data_smz_f1_rt2 _audit_creation_method SHELXL-2014/6 _chemical_name_systematic ' 4-amino-N-(4-methylpyrimidin-2-yl) ' _chemical_name_common ' Sulfamerazine ' _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N4 O2 S' _chemical_formula_sum 'C11 H12 N4 O2 S' _chemical_formula_weight 264.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_H-M_alt 'P n a 21' _space_group_name_Hall 'P 2c -2n' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 14.4902(9) _cell_length_b 8.2249(6) _cell_length_c 22.0106(14) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2623.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293.0(2) _cell_measurement_reflns_used 1876 _cell_measurement_theta_min 3.8590 _cell_measurement_theta_max 26.9580 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_F_000 1104 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_absorpt_coefficient_mu 0.247 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89972 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; 'Thu Dec 11 01:21:55 2014' ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 293.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 7706 _diffrn_reflns_av_unetI/netI 0.0657 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.367 _diffrn_reflns_theta_max 29.116 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.863 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.679 _diffrn_reflns_point_group_measured_fraction_full 0.816 _reflns_number_total 4785 _reflns_number_gt 3259 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.535 _reflns_Friedel_fraction_max 0.485 _reflns_Friedel_fraction_full 0.625 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; 'Thu Dec 11 01:21:55 2014' ; _computing_cell_refinement ; 'Thu Dec 11 01:21:55 2014' ; _computing_data_reduction ; 'Thu Dec 11 01:21:55 2014' ; _computing_structure_solution 'SHELXT' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics 'OSCAIL' _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0366P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 941 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.02(7) _chemical_absolute_configuration ad _refine_ls_number_reflns 4785 _refine_ls_number_parameters 343 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.949 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.64733(9) 0.49675(15) 0.34465(7) 0.0402(3) Uani 1 1 d . . . . . S2 S 0.57774(9) 0.49469(15) 0.65218(7) 0.0394(3) Uani 1 1 d . . . . . O1 O 0.6902(3) 0.3726(4) 0.30896(18) 0.0526(10) Uani 1 1 d . . . . . O2 O 0.5502(2) 0.5231(4) 0.33785(19) 0.0514(9) Uani 1 1 d . . . . . O3 O 0.6746(2) 0.4662(4) 0.65829(18) 0.0508(9) Uani 1 1 d . . . . . O4 O 0.5356(3) 0.6221(4) 0.68633(16) 0.0497(10) Uani 1 1 d . . . . . N1 N 0.8432(4) 1.1154(6) 0.3125(3) 0.0601(14) Uani 1 1 d D . . . . N2 N 0.6569(3) 0.4499(6) 0.4177(2) 0.0430(11) Uani 1 1 d D . . . . N3 N 0.8153(3) 0.4107(5) 0.4179(2) 0.0460(12) Uani 1 1 d . . . . . N4 N 0.7284(4) 0.4265(6) 0.5095(2) 0.0591(14) Uani 1 1 d . . . . . N5 N 0.3810(4) -0.1196(6) 0.6967(3) 0.0788(19) Uani 1 1 d . . . . . H5A H 0.4087 -0.2107 0.6907 0.102 Uiso 1 1 calc R U . . . H5B H 0.3247 -0.1186 0.7090 0.102 Uiso 1 1 calc R U . . . N6 N 0.5679(3) 0.5355(6) 0.5793(2) 0.0471(12) Uani 1 1 d D . . . . N7 N 0.4105(3) 0.5843(5) 0.5798(2) 0.0481(12) Uani 1 1 d . . . . . N8 N 0.4963(4) 0.5661(7) 0.4875(2) 0.0613(14) Uani 1 1 d . . . . . C1 C 0.7065(4) 0.6782(6) 0.3345(3) 0.0363(12) Uani 1 1 d . . . . . C2 C 0.7951(3) 0.6811(6) 0.3111(2) 0.0386(12) Uani 1 1 d . . . . . H2 H 0.8241 0.5842 0.3006 0.050 Uiso 1 1 calc R U . . . C3 C 0.8404(4) 0.8253(6) 0.3034(3) 0.0400(13) Uani 1 1 d . . . . . H3 H 0.9000 0.8256 0.2877 0.052 Uiso 1 1 calc R U . . . C4 C 0.7979(4) 0.9731(6) 0.3187(2) 0.0405(12) Uani 1 1 d . . . . . C5 C 0.7089(4) 0.9675(6) 0.3428(3) 0.0473(14) Uani 1 1 d . . . . . H5 H 0.6801 1.0638 0.3543 0.061 Uiso 1 1 calc R U . . . C6 C 0.6631(4) 0.8236(6) 0.3499(3) 0.0447(13) Uani 1 1 d . . . . . H6 H 0.6032 0.8227 0.3650 0.058 Uiso 1 1 calc R U . . . C7 C 0.7376(4) 0.4298(6) 0.4492(2) 0.0419(13) Uani 1 1 d . . . . . C8 C 0.8058(4) 0.3997(10) 0.5408(3) 0.081(2) Uani 1 1 d . . . . . H8 H 0.8025 0.3924 0.5829 0.106 Uiso 1 1 calc R U . . . C9 C 0.8900(4) 0.3823(9) 0.5132(3) 0.076(2) Uani 1 1 d . . . . . H9 H 0.9434 0.3668 0.5359 0.098 Uiso 1 1 calc R U . . . C10 C 0.8929(4) 0.3888(7) 0.4504(3) 0.0551(16) Uani 1 1 d . . . . . C11 C 0.9800(5) 0.3731(9) 0.4149(4) 0.080(2) Uani 1 1 d . . . . . H11A H 0.9786 0.2741 0.3917 0.104 Uiso 1 1 calc R U . . . H11B H 1.0317 0.3709 0.4422 0.104 Uiso 1 1 calc R U . . . H11C H 0.9859 0.4640 0.3878 0.104 Uiso 1 1 calc R U . . . C12 C 0.5188(4) 0.3142(6) 0.6656(2) 0.0383(12) Uani 1 1 d . . . . . C13 C 0.5643(4) 0.1687(6) 0.6558(3) 0.0511(16) Uani 1 1 d . . . . . H13 H 0.6251 0.1680 0.6422 0.066 Uiso 1 1 calc R U . . . C14 C 0.5181(4) 0.0236(7) 0.6666(3) 0.0574(17) Uani 1 1 d . . . . . H14 H 0.5483 -0.0748 0.6605 0.075 Uiso 1 1 calc R U . . . C15 C 0.4268(4) 0.0241(6) 0.6866(3) 0.0495(15) Uani 1 1 d . . . . . C16 C 0.3822(4) 0.1722(6) 0.6966(2) 0.0429(13) Uani 1 1 d . . . . . H16 H 0.3214 0.1739 0.7100 0.056 Uiso 1 1 calc R U . . . C17 C 0.4286(4) 0.3159(6) 0.6865(3) 0.0382(13) Uani 1 1 d . . . . . H17 H 0.3993 0.4145 0.6939 0.050 Uiso 1 1 calc R U . . . C18 C 0.4872(4) 0.5638(6) 0.5480(2) 0.0418(13) Uani 1 1 d . . . . . C19 C 0.4194(5) 0.5980(11) 0.4574(3) 0.090(3) Uani 1 1 d . . . . . H19 H 0.4217 0.6017 0.4152 0.117 Uiso 1 1 calc R U . . . C20 C 0.3371(5) 0.6258(10) 0.4853(3) 0.085(2) Uani 1 1 d . . . . . H20 H 0.2847 0.6516 0.4629 0.110 Uiso 1 1 calc R U . . . C21 C 0.3338(5) 0.6146(7) 0.5474(3) 0.0566(16) Uani 1 1 d . . . . . C22 C 0.2455(4) 0.6353(9) 0.5820(4) 0.084(2) Uani 1 1 d . . . . . H22A H 0.2005 0.5596 0.5672 0.109 Uiso 1 1 calc R U . . . H22B H 0.2231 0.7442 0.5767 0.109 Uiso 1 1 calc R U . . . H22C H 0.2565 0.6154 0.6244 0.109 Uiso 1 1 calc R U . . . H1N1 H 0.895(2) 1.113(6) 0.293(2) 0.051(16) Uiso 1 1 d D . . . . H2N1 H 0.805(3) 1.200(4) 0.314(2) 0.053(17) Uiso 1 1 d D . . . . H1N2 H 0.609(3) 0.486(6) 0.440(2) 0.055(18) Uiso 1 1 d D . . . . H1N6 H 0.616(3) 0.496(7) 0.558(3) 0.09(3) Uiso 1 1 d D . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0371(7) 0.0435(7) 0.0399(7) 0.0035(7) -0.0020(6) -0.0025(6) S2 0.0351(7) 0.0458(7) 0.0374(7) 0.0043(7) -0.0026(6) -0.0025(6) O1 0.055(3) 0.044(2) 0.059(2) -0.008(2) -0.001(2) -0.0065(18) O2 0.0341(19) 0.069(2) 0.051(2) 0.010(2) -0.007(2) -0.0084(18) O3 0.037(2) 0.065(2) 0.050(2) 0.011(2) -0.008(2) -0.0013(17) O4 0.056(3) 0.044(2) 0.049(2) -0.0077(19) 0.000(2) 0.0006(18) N1 0.052(3) 0.045(3) 0.083(4) -0.011(3) 0.023(3) -0.004(3) N2 0.030(2) 0.060(3) 0.040(3) 0.012(3) 0.003(2) 0.002(2) N3 0.041(3) 0.047(2) 0.050(3) 0.011(2) 0.001(2) 0.003(2) N4 0.042(3) 0.096(4) 0.039(3) 0.010(3) -0.002(2) 0.014(3) N5 0.067(4) 0.042(3) 0.128(5) -0.006(3) 0.034(4) -0.011(2) N6 0.034(3) 0.069(3) 0.038(3) 0.015(3) 0.002(2) 0.006(2) N7 0.042(3) 0.054(3) 0.048(3) 0.003(2) 0.001(2) 0.007(2) N8 0.047(3) 0.093(4) 0.043(3) 0.006(3) 0.000(3) 0.016(3) C1 0.036(3) 0.038(2) 0.035(3) 0.002(2) 0.003(3) 0.005(2) C2 0.035(3) 0.046(3) 0.034(3) 0.000(3) 0.000(2) 0.006(2) C3 0.035(3) 0.049(3) 0.035(3) -0.002(3) 0.007(3) -0.001(2) C4 0.042(3) 0.043(3) 0.037(3) -0.003(2) -0.001(2) -0.001(2) C5 0.048(3) 0.039(3) 0.056(3) -0.007(3) 0.013(3) 0.003(2) C6 0.038(3) 0.047(3) 0.048(3) 0.001(3) 0.009(3) 0.003(2) C7 0.036(3) 0.045(3) 0.044(3) 0.008(3) 0.003(3) 0.002(2) C8 0.050(4) 0.144(7) 0.050(4) 0.003(4) -0.008(4) 0.025(4) C9 0.038(4) 0.129(6) 0.059(4) 0.002(4) -0.010(4) 0.023(4) C10 0.039(3) 0.059(4) 0.067(4) 0.004(3) -0.005(3) 0.007(3) C11 0.052(4) 0.094(5) 0.094(5) -0.006(5) 0.006(5) 0.011(4) C12 0.036(3) 0.038(2) 0.041(3) 0.004(2) -0.001(3) -0.001(2) C13 0.037(3) 0.045(3) 0.071(4) -0.007(3) 0.011(4) 0.005(2) C14 0.046(3) 0.045(3) 0.080(5) -0.002(3) 0.015(3) 0.011(3) C15 0.057(4) 0.044(3) 0.048(3) -0.004(3) 0.004(3) -0.006(3) C16 0.038(3) 0.048(3) 0.043(3) -0.007(3) 0.006(3) -0.004(2) C17 0.038(3) 0.038(3) 0.038(3) -0.005(3) 0.002(3) 0.002(2) C18 0.033(3) 0.046(3) 0.046(3) 0.010(3) -0.004(3) 0.002(2) C19 0.064(5) 0.159(8) 0.046(4) 0.011(5) -0.012(4) 0.027(5) C20 0.048(4) 0.135(7) 0.071(5) -0.008(5) -0.011(4) 0.035(4) C21 0.045(4) 0.063(4) 0.062(4) -0.004(3) 0.004(3) 0.010(3) C22 0.037(4) 0.120(6) 0.093(5) -0.001(5) 0.004(4) 0.015(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.430(4) . ? S1 O2 1.432(4) . ? S1 N2 1.659(5) . ? S1 C1 1.735(5) . ? S2 O4 1.427(4) . ? S2 O3 1.429(4) . ? S2 N6 1.646(5) . ? S2 C12 1.738(5) . ? N1 C4 1.349(7) . ? N1 H1N1 0.87(2) . ? N1 H2N1 0.89(2) . ? N2 C7 1.370(7) . ? N2 H1N2 0.90(2) . ? N3 C7 1.329(6) . ? N3 C10 1.344(7) . ? N4 C8 1.334(8) . ? N4 C7 1.335(7) . ? N5 C15 1.373(7) . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? N6 C18 1.376(6) . ? N6 H1N6 0.91(2) . ? N7 C18 1.325(6) . ? N7 C21 1.343(8) . ? N8 C19 1.322(8) . ? N8 C18 1.337(7) . ? C1 C2 1.384(7) . ? C1 C6 1.393(7) . ? C2 C3 1.366(7) . ? C2 H2 0.9300 . ? C3 C4 1.404(7) . ? C3 H3 0.9300 . ? C4 C5 1.396(7) . ? C5 C6 1.366(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.370(9) . ? C8 H8 0.9300 . ? C9 C10 1.384(10) . ? C9 H9 0.9300 . ? C10 C11 1.491(8) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.383(7) . ? C12 C17 1.386(7) . ? C13 C14 1.389(8) . ? C13 H13 0.9300 . ? C14 C15 1.394(8) . ? C14 H14 0.9300 . ? C15 C16 1.396(7) . ? C16 C17 1.377(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C19 C20 1.361(10) . ? C19 H19 0.9300 . ? C20 C21 1.371(10) . ? C20 H20 0.9300 . ? C21 C22 1.498(8) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 118.5(2) . . ? O1 S1 N2 109.3(2) . . ? O2 S1 N2 102.6(2) . . ? O1 S1 C1 109.2(3) . . ? O2 S1 C1 110.0(2) . . ? N2 S1 C1 106.5(3) . . ? O4 S2 O3 119.4(2) . . ? O4 S2 N6 109.1(2) . . ? O3 S2 N6 102.2(2) . . ? O4 S2 C12 109.1(3) . . ? O3 S2 C12 109.1(2) . . ? N6 S2 C12 107.3(3) . . ? C4 N1 H1N1 117(3) . . ? C4 N1 H2N1 112(3) . . ? H1N1 N1 H2N1 125(5) . . ? C7 N2 S1 126.1(4) . . ? C7 N2 H1N2 116(4) . . ? S1 N2 H1N2 112(4) . . ? C7 N3 C10 116.7(5) . . ? C8 N4 C7 115.6(6) . . ? C15 N5 H5A 120.0 . . ? C15 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C18 N6 S2 126.6(4) . . ? C18 N6 H1N6 117(5) . . ? S2 N6 H1N6 112(5) . . ? C18 N7 C21 116.0(5) . . ? C19 N8 C18 114.8(6) . . ? C2 C1 C6 119.6(5) . . ? C2 C1 S1 121.4(4) . . ? C6 C1 S1 119.0(4) . . ? C3 C2 C1 120.5(5) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.8(5) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? N1 C4 C5 121.1(5) . . ? N1 C4 C3 120.9(5) . . ? C5 C4 C3 117.9(5) . . ? C6 C5 C4 121.4(5) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 119.9(5) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N3 C7 N4 126.7(6) . . ? N3 C7 N2 118.4(5) . . ? N4 C7 N2 114.9(5) . . ? N4 C8 C9 122.5(6) . . ? N4 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C8 C9 C10 117.7(7) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? N3 C10 C9 120.7(6) . . ? N3 C10 C11 116.2(6) . . ? C9 C10 C11 123.1(7) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 120.7(5) . . ? C13 C12 S2 118.6(4) . . ? C17 C12 S2 120.7(4) . . ? C12 C13 C14 119.1(5) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 120.6(5) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? N5 C15 C14 120.4(5) . . ? N5 C15 C16 120.2(5) . . ? C14 C15 C16 119.4(5) . . ? C17 C16 C15 119.8(5) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C12 120.3(5) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? N7 C18 N8 127.3(5) . . ? N7 C18 N6 118.0(5) . . ? N8 C18 N6 114.7(5) . . ? N8 C19 C20 123.0(7) . . ? N8 C19 H19 118.5 . . ? C20 C19 H19 118.5 . . ? C19 C20 C21 118.1(7) . . ? C19 C20 H20 121.0 . . ? C21 C20 H20 121.0 . . ? N7 C21 C20 120.8(6) . . ? N7 C21 C22 117.3(6) . . ? C20 C21 C22 122.0(7) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N2 C7 60.6(5) . . . . ? O2 S1 N2 C7 -172.8(5) . . . . ? C1 S1 N2 C7 -57.2(5) . . . . ? O4 S2 N6 C18 -56.5(6) . . . . ? O3 S2 N6 C18 176.2(5) . . . . ? C12 S2 N6 C18 61.6(6) . . . . ? O1 S1 C1 C2 -18.1(5) . . . . ? O2 S1 C1 C2 -149.8(4) . . . . ? N2 S1 C1 C2 99.8(5) . . . . ? O1 S1 C1 C6 161.5(4) . . . . ? O2 S1 C1 C6 29.9(5) . . . . ? N2 S1 C1 C6 -80.6(5) . . . . ? C6 C1 C2 C3 0.3(8) . . . . ? S1 C1 C2 C3 179.9(4) . . . . ? C1 C2 C3 C4 -0.2(8) . . . . ? C2 C3 C4 N1 178.5(5) . . . . ? C2 C3 C4 C5 0.9(8) . . . . ? N1 C4 C5 C6 -179.2(6) . . . . ? C3 C4 C5 C6 -1.7(9) . . . . ? C4 C5 C6 C1 1.8(9) . . . . ? C2 C1 C6 C5 -1.0(8) . . . . ? S1 C1 C6 C5 179.3(5) . . . . ? C10 N3 C7 N4 -1.3(9) . . . . ? C10 N3 C7 N2 -179.0(5) . . . . ? C8 N4 C7 N3 -0.7(9) . . . . ? C8 N4 C7 N2 177.1(6) . . . . ? S1 N2 C7 N3 -15.5(8) . . . . ? S1 N2 C7 N4 166.5(4) . . . . ? C7 N4 C8 C9 2.3(11) . . . . ? N4 C8 C9 C10 -1.8(12) . . . . ? C7 N3 C10 C9 1.8(9) . . . . ? C7 N3 C10 C11 -178.0(5) . . . . ? C8 C9 C10 N3 -0.3(11) . . . . ? C8 C9 C10 C11 179.5(7) . . . . ? O4 S2 C12 C13 -157.1(4) . . . . ? O3 S2 C12 C13 -25.1(5) . . . . ? N6 S2 C12 C13 84.9(5) . . . . ? O4 S2 C12 C17 21.8(5) . . . . ? O3 S2 C12 C17 153.8(4) . . . . ? N6 S2 C12 C17 -96.2(5) . . . . ? C17 C12 C13 C14 0.8(9) . . . . ? S2 C12 C13 C14 179.7(5) . . . . ? C12 C13 C14 C15 0.5(9) . . . . ? C13 C14 C15 N5 179.4(6) . . . . ? C13 C14 C15 C16 -1.0(9) . . . . ? N5 C15 C16 C17 179.8(5) . . . . ? C14 C15 C16 C17 0.2(8) . . . . ? C15 C16 C17 C12 1.1(8) . . . . ? C13 C12 C17 C16 -1.6(8) . . . . ? S2 C12 C17 C16 179.5(4) . . . . ? C21 N7 C18 N8 -1.7(9) . . . . ? C21 N7 C18 N6 178.8(5) . . . . ? C19 N8 C18 N7 2.4(10) . . . . ? C19 N8 C18 N6 -178.1(6) . . . . ? S2 N6 C18 N7 10.6(8) . . . . ? S2 N6 C18 N8 -168.9(5) . . . . ? C18 N8 C19 C20 -0.3(12) . . . . ? N8 C19 C20 C21 -2.2(14) . . . . ? C18 N7 C21 C20 -1.1(9) . . . . ? C18 N7 C21 C22 178.9(6) . . . . ? C19 C20 C21 N7 2.9(12) . . . . ? C19 C20 C21 C22 -177.1(7) . . . . ? _refine_diff_density_max 0.264 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.057 _shelxl_version_number 2014/6 _shelx_res_file ; TITL smz_f1_rt2_a.res in Pna2(1) REM Old TITL smz_f1_rt2 in Pnma REM SHELXT solution in Pna2(1) REM R1 0.129, Rweak 0.194, Alpha 0.008, Orientation a'=-a, b'=c, c'=b REM Flack x = 0.018 ( 0.070 ) from Parsons' quotients REM Formula found by SHELXT: C25 N4 O5 S2 CELL 0.71073 14.4902 8.2249 22.0106 90.000 90.000 90.000 ZERR 8.000 0.0009 0.0006 0.0014 0.000 0.000 0.000 REM SG 33 4 4 Pna21 PGmm2 Orthorhombic LATT -1 REM SG ASUN 1 .5 .5 1. REM SG ORGN on 2(1) SYMM -X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,Z SYMM 0.5-X,0.5+Y,0.5+Z SFAC C H N O S UNIT 88 96 32 16 8 FMAP 2 PLAN -32 BOND $H L.S. 12 ACTA CONF HTAB LIST 4 DFIX .89 .02 N1 H1N1 N1 H2N1 N2 H1N2 N6 H1N6 WGHT 0.036600 FVAR 0.35522 S1 5 0.647330 0.496752 0.344652 11.00000 0.03705 0.04349 = 0.03994 0.00349 -0.00202 -0.00252 S2 5 0.577736 0.494690 0.652177 11.00000 0.03507 0.04579 = 0.03740 0.00430 -0.00256 -0.00246 O1 4 0.690196 0.372565 0.308964 11.00000 0.05492 0.04420 = 0.05857 -0.00842 -0.00115 -0.00650 O2 4 0.550160 0.523068 0.337852 11.00000 0.03409 0.06875 = 0.05138 0.00991 -0.00715 -0.00836 O3 4 0.674587 0.466245 0.658294 11.00000 0.03724 0.06530 = 0.04972 0.01094 -0.00845 -0.00133 O4 4 0.535600 0.622145 0.686327 11.00000 0.05608 0.04402 = 0.04895 -0.00775 0.00005 0.00065 N1 3 0.843202 1.115412 0.312474 11.00000 0.05200 0.04534 = 0.08306 -0.01060 0.02334 -0.00390 N2 3 0.656862 0.449935 0.417712 11.00000 0.02960 0.05977 = 0.03960 0.01201 0.00259 0.00167 N3 3 0.815257 0.410683 0.417948 11.00000 0.04140 0.04656 = 0.05011 0.01071 0.00119 0.00342 N4 3 0.728400 0.426534 0.509544 11.00000 0.04234 0.09610 = 0.03898 0.00955 -0.00243 0.01408 N5 3 0.381047 -0.119630 0.696675 11.00000 0.06667 0.04190 = 0.12772 -0.00623 0.03366 -0.01076 AFIX 93 H5A 2 0.408750 -0.210712 0.690706 11.00000 -1.30000 H5B 2 0.324717 -0.118561 0.708974 11.00000 -1.30000 AFIX 0 N6 3 0.567865 0.535479 0.579250 11.00000 0.03419 0.06884 = 0.03837 0.01531 0.00167 0.00644 N7 3 0.410450 0.584341 0.579766 11.00000 0.04177 0.05421 = 0.04834 0.00262 0.00099 0.00692 N8 3 0.496283 0.566109 0.487495 11.00000 0.04715 0.09335 = 0.04334 0.00561 -0.00028 0.01625 C1 1 0.706458 0.678157 0.334451 11.00000 0.03620 0.03830 = 0.03452 0.00223 0.00293 0.00534 C2 1 0.795123 0.681099 0.311085 11.00000 0.03541 0.04603 = 0.03450 0.00009 0.00037 0.00601 AFIX 43 H2 2 0.824096 0.584210 0.300568 11.00000 -1.30000 AFIX 0 C3 1 0.840355 0.825300 0.303367 11.00000 0.03525 0.04949 = 0.03513 -0.00162 0.00702 -0.00142 AFIX 43 H3 2 0.899987 0.825568 0.287743 11.00000 -1.30000 AFIX 0 C4 1 0.797919 0.973139 0.318734 11.00000 0.04204 0.04257 = 0.03684 -0.00277 -0.00072 -0.00106 C5 1 0.708897 0.967542 0.342833 11.00000 0.04752 0.03874 = 0.05559 -0.00715 0.01330 0.00320 AFIX 43 H5 2 0.680126 1.063833 0.354315 11.00000 -1.30000 AFIX 0 C6 1 0.663150 0.823634 0.349909 11.00000 0.03841 0.04738 = 0.04845 0.00074 0.00924 0.00325 AFIX 43 H6 2 0.603212 0.822730 0.365014 11.00000 -1.30000 AFIX 0 C7 1 0.737559 0.429768 0.449212 11.00000 0.03643 0.04539 = 0.04373 0.00773 0.00285 0.00220 C8 1 0.805825 0.399672 0.540796 11.00000 0.05018 0.14354 = 0.05018 0.00314 -0.00812 0.02470 AFIX 43 H8 2 0.802510 0.392441 0.582905 11.00000 -1.30000 AFIX 0 C9 1 0.890005 0.382342 0.513219 11.00000 0.03818 0.12950 = 0.05911 0.00177 -0.01029 0.02279 AFIX 43 H9 2 0.943404 0.366756 0.535925 11.00000 -1.30000 AFIX 0 C10 1 0.892873 0.388822 0.450397 11.00000 0.03930 0.05940 = 0.06655 0.00353 -0.00451 0.00686 C11 1 0.980022 0.373068 0.414877 11.00000 0.05182 0.09422 = 0.09381 -0.00627 0.00565 0.01062 AFIX 137 H11A 2 0.978580 0.274149 0.391745 11.00000 -1.30000 H11B 2 1.031656 0.370893 0.442193 11.00000 -1.30000 H11C 2 0.985947 0.464017 0.387821 11.00000 -1.30000 AFIX 0 C12 1 0.518781 0.314174 0.665568 11.00000 0.03584 0.03808 = 0.04089 0.00386 -0.00145 -0.00112 C13 1 0.564326 0.168709 0.655829 11.00000 0.03744 0.04516 = 0.07081 -0.00741 0.01132 0.00495 AFIX 43 H13 2 0.625092 0.168047 0.642233 11.00000 -1.30000 AFIX 0 C14 1 0.518088 0.023618 0.666628 11.00000 0.04648 0.04540 = 0.08041 -0.00165 0.01456 0.01118 AFIX 43 H14 2 0.548333 -0.074753 0.660500 11.00000 -1.30000 AFIX 0 C15 1 0.426754 0.024080 0.686570 11.00000 0.05689 0.04399 = 0.04750 -0.00443 0.00368 -0.00550 C16 1 0.382210 0.172220 0.696581 11.00000 0.03820 0.04760 = 0.04296 -0.00678 0.00612 -0.00426 AFIX 43 H16 2 0.321357 0.173876 0.709995 11.00000 -1.30000 AFIX 0 C17 1 0.428604 0.315880 0.686545 11.00000 0.03841 0.03805 = 0.03808 -0.00475 0.00189 0.00208 AFIX 43 H17 2 0.399274 0.414520 0.693880 11.00000 -1.30000 AFIX 0 C18 1 0.487237 0.563820 0.547952 11.00000 0.03325 0.04629 = 0.04598 0.00966 -0.00419 0.00194 C19 1 0.419446 0.598041 0.457364 11.00000 0.06431 0.15933 = 0.04644 0.01137 -0.01182 0.02727 AFIX 43 H19 2 0.421736 0.601693 0.415160 11.00000 -1.30000 AFIX 0 C20 1 0.337137 0.625814 0.485323 11.00000 0.04784 0.13505 = 0.07074 -0.00791 -0.01138 0.03523 AFIX 43 H20 2 0.284712 0.651631 0.462939 11.00000 -1.30000 AFIX 0 C21 1 0.333764 0.614622 0.547438 11.00000 0.04483 0.06277 = 0.06217 -0.00404 0.00405 0.00963 C22 1 0.245541 0.635304 0.582033 11.00000 0.03732 0.12030 = 0.09349 -0.00113 0.00354 0.01468 AFIX 137 H22A 2 0.200484 0.559565 0.567151 11.00000 -1.30000 H22B 2 0.223088 0.744192 0.576722 11.00000 -1.30000 H22C 2 0.256499 0.615412 0.624400 11.00000 -1.30000 AFIX 0 H1N1 2 0.895346 1.112744 0.292541 11.00000 0.05100 H2N1 2 0.804972 1.199652 0.313785 11.00000 0.05348 H1N2 2 0.608528 0.485612 0.439655 11.00000 0.05482 H1N6 2 0.616316 0.496020 0.557721 11.00000 0.08953 HKLF 4 REM smz_f1_rt2_a.res in Pna2(1) REM R1 = 0.0487 for 3259 Fo > 4sig(Fo) and 0.0773 for all 4785 data REM 343 parameters refined using 5 restraints END WGHT 0.0298 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 x, y-1, z HTAB N5 O4_$1 HTAB C8 O3 HTAB C14 O4_$1 HTAB C19 O2 EQIV $2 -x+3/2, y+1/2, z-1/2 HTAB N1 O4_$2 EQIV $3 x, y+1, z HTAB N1 O1_$3 HTAB N2 N8 HTAB N6 N4 REM Highest difference peak 0.264, deepest hole -0.328, 1-sigma level 0.057 Q1 1 0.5194 0.3727 0.3385 11.00000 0.05 0.21 Q2 1 0.5397 0.6558 0.3417 11.00000 0.05 0.20 Q3 1 0.7005 0.3789 0.6536 11.00000 0.05 0.19 Q4 1 1.0422 0.2708 0.3468 11.00000 0.05 0.18 Q5 1 0.6799 0.3532 0.6226 11.00000 0.05 0.18 Q6 1 0.7885 0.2747 0.5767 11.00000 0.05 0.18 Q7 1 0.2237 0.4833 0.5999 11.00000 0.05 0.18 Q8 1 0.5454 0.7724 0.3756 11.00000 0.05 0.18 Q9 1 0.7423 0.2588 0.6266 11.00000 0.05 0.17 Q10 1 1.0382 0.2505 0.3653 11.00000 0.05 0.17 Q11 1 0.5325 0.4730 0.3808 11.00000 0.05 0.17 Q12 1 0.9821 0.2012 0.3912 11.00000 0.05 0.17 Q13 1 0.2598 0.7450 0.6680 11.00000 0.05 0.17 Q14 1 0.5804 0.7269 0.6204 11.00000 0.05 0.16 Q15 1 0.6754 0.3654 0.6755 11.00000 0.05 0.16 Q16 1 0.6858 0.2579 0.6605 11.00000 0.05 0.16 Q17 1 0.2468 0.3898 0.5940 11.00000 0.05 0.16 Q18 1 0.6656 0.6749 0.6804 11.00000 0.05 0.16 Q19 1 0.9858 0.1445 0.4114 11.00000 0.05 0.16 Q20 1 0.5630 0.3737 0.6689 11.00000 0.05 0.16 Q21 1 0.6554 0.6196 0.3231 11.00000 0.05 0.16 Q22 1 0.4384 0.7504 0.4261 11.00000 0.05 0.15 Q23 1 0.5389 0.8250 0.3420 11.00000 0.05 0.15 Q24 1 0.6684 0.5114 0.6595 11.00000 0.05 0.15 Q25 1 0.7758 0.3875 0.6619 11.00000 0.05 0.15 Q26 1 0.3156 0.6267 0.5687 11.00000 0.05 0.15 Q27 1 0.2465 0.6835 0.6565 11.00000 0.05 0.15 Q28 1 0.4977 0.6465 0.3899 11.00000 0.05 0.15 Q29 1 0.7978 0.4730 0.5918 11.00000 0.05 0.15 Q30 1 0.7034 0.2282 0.5719 11.00000 0.05 0.15 Q31 1 0.5988 0.3938 0.2304 11.00000 0.05 0.15 Q32 1 0.7076 0.5937 0.6585 11.00000 0.05 0.15 ; _shelx_res_checksum 34787 _shelx_hkl_file ; 0 0 4 1989.34 21.45 0 0 -4 1959.63 16.30 0 0 -4 2022.67 21.26 0 0 5 1.58 1.22 0 0 -5 3.77 2.00 0 0 5 1.35 1.16 0 0 6 9716.39 43.58 0 0 -6 9999.00 44.70 0 0 6 9620.93 57.88 0 0 -6 9647.40 57.13 0 0 7 22.56 3.44 0 0 -7 12.80 2.44 0 0 7 10.57 2.68 0 0 8 6715.19 42.20 0 0 -8 7015.81 43.30 0 0 -8 6871.24 55.74 0 0 8 6822.65 56.30 0 0 9 32.14 4.52 0 0 -9 32.13 4.03 0 0 -10 251.27 11.92 0 0 -10 251.57 9.25 0 0 10 250.94 12.07 0 0 -11 2.46 1.12 0 0 -11 3.93 2.53 0 0 -12 1574.71 33.01 0 0 -12 1552.00 25.16 0 0 -13 23.40 3.40 0 0 -13 21.59 5.69 0 0 -14 42.67 6.00 0 0 -14 39.79 4.30 0 0 -15 1.14 1.18 0 0 -15 3.07 1.57 0 0 -16 129.61 8.42 0 0 -16 134.93 11.34 0 0 -17 6.09 2.38 0 0 -17 3.43 2.12 0 0 -18 28.57 5.61 0 0 -19 2.60 2.13 0 0 -20 222.76 16.64 0 0 -21 7.82 3.69 0 0 -22 19.68 5.37 0 0 -23 -1.24 1.93 0 0 -24 -1.81 1.35 0 0 -25 2.71 2.74 0 0 -26 184.37 18.10 0 0 -27 7.47 3.88 0 0 -28 51.31 10.13 0 0 -29 4.05 3.42 1 0 4 0.59 0.45 1 0 -4 2.90 1.27 1 0 -4 0.57 0.47 -1 0 4 -0.05 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1996.70 26.48 -1 2 -2 1947.37 24.38 1 -2 -2 2037.51 27.78 -1 2 -2 1979.87 21.66 -1 -2 3 631.56 15.42 -1 2 -3 635.56 15.08 1 -2 3 623.42 12.93 1 2 -3 635.28 15.57 1 -2 3 634.59 15.31 1 -2 -3 627.52 16.23 1 2 -3 630.70 15.45 -1 2 -3 620.99 13.00 -1 2 -4 85.34 5.91 1 2 -4 83.51 5.91 1 -2 -4 83.21 6.12 1 -2 4 82.26 5.87 -1 -2 4 81.43 5.73 1 2 -4 76.49 5.74 -1 2 -4 78.18 4.96 -1 2 -5 14.56 2.27 1 2 -5 13.74 2.56 1 2 -5 13.87 2.55 1 -2 5 14.66 2.58 1 -2 -5 14.72 2.64 -1 2 -5 13.85 2.63 1 2 -6 86.47 6.52 1 -2 6 79.47 6.62 -1 2 -6 82.71 5.74 -1 2 -6 77.20 6.49 1 2 6 78.44 4.18 1 -2 -6 77.38 3.26 1 2 -6 82.82 6.65 1 -2 -6 84.74 6.46 -1 2 -7 79.05 6.88 1 2 7 77.44 4.51 1 -2 -7 80.94 6.61 1 2 -7 82.29 6.72 1 -2 -7 78.03 3.91 1 2 -7 80.15 7.06 1 2 8 59.43 4.30 1 2 -8 58.44 6.27 1 -2 -8 55.32 3.72 -1 2 -8 56.95 6.29 -1 2 -9 86.87 7.97 1 -2 -9 85.77 5.17 1 2 9 84.11 5.56 1 2 -9 92.01 8.14 1 2 -10 29.44 4.78 -1 -2 10 37.13 3.53 1 2 10 26.05 3.35 1 -2 -10 24.55 3.03 -1 2 -10 25.74 4.58 1 2 -11 2.52 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3.12 2 2 -6 17.34 3.17 -2 2 -6 16.76 3.21 2 -2 -6 16.37 3.03 2 -2 6 13.96 1.41 -2 2 7 313.69 13.62 2 -2 -7 321.59 8.54 2 2 7 317.38 10.41 -2 2 -7 309.53 13.89 2 2 -7 317.86 14.26 -2 2 8 22.83 3.79 2 2 -8 19.48 3.50 2 2 8 19.81 2.74 2 -2 -8 19.76 2.31 -2 2 -8 19.85 3.90 2 2 9 310.14 11.53 2 2 -9 306.68 15.27 -2 2 -9 312.68 15.45 2 -2 -9 307.48 10.23 -2 2 9 317.29 14.33 2 2 10 63.54 5.52 2 2 -10 66.82 7.33 -2 2 -10 63.37 7.34 2 -2 -10 61.59 4.93 -2 2 10 68.65 6.83 2 2 -11 2.94 1.94 2 -2 -11 2.11 0.90 -2 -2 11 9.26 2.77 -2 2 -11 2.54 1.97 2 2 11 4.13 1.44 -2 2 -12 103.03 9.79 2 -2 -12 100.38 7.08 -2 -2 12 99.89 6.55 2 2 -12 104.94 9.92 2 -2 -13 396.67 14.99 2 2 -13 415.90 20.42 -2 -2 13 399.75 13.23 -2 2 -13 401.86 20.10 -2 -2 14 1.74 0.61 -2 2 -14 5.36 3.03 2 -2 -14 3.89 1.89 2 2 -14 4.64 2.60 2 2 -15 13.36 3.78 -2 -2 15 10.34 1.85 -2 2 -15 14.54 3.95 2 -2 -15 12.74 2.76 -2 -2 16 3.42 1.33 2 2 -16 1.84 1.90 -2 2 -16 3.00 1.37 2 -2 -16 2.83 1.65 2 -2 -17 128.43 10.25 -2 2 -17 123.81 12.52 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2.36 -3 -8 -3 6.75 2.41 3 8 -4 16.28 4.38 3 -8 4 15.50 4.05 -3 -8 4 17.22 5.21 3 8 -5 6.80 3.03 3 -8 5 6.78 2.95 -3 -8 5 6.53 3.44 3 8 -6 0.46 1.37 -3 -8 6 0.24 0.88 3 8 -7 5.81 2.80 -3 -8 7 7.44 3.72 -3 8 -7 4.41 2.46 3 8 -8 5.48 2.85 -3 -8 8 9.32 4.24 -3 8 -8 5.97 2.74 3 8 -9 11.99 4.39 -3 -8 9 16.85 5.21 -3 8 -9 10.58 3.84 -3 8 -10 3.40 2.49 3 8 -10 2.39 1.67 -3 8 -11 1.98 1.91 3 8 -11 1.73 2.04 -3 8 -12 7.59 3.89 3 8 -12 4.71 2.82 -3 8 -13 20.32 6.19 3 8 -13 18.71 5.81 -3 8 -14 1.92 1.94 3 8 -14 5.45 3.29 -3 8 -15 6.34 3.34 3 8 -15 8.50 4.07 -3 8 -16 3.55 3.03 3 8 -16 1.31 1.92 -3 8 -17 5.39 3.73 3 8 -17 1.24 1.68 -3 8 -18 1.29 2.05 -4 -8 0 47.40 8.64 4 8 0 53.05 7.29 -4 -8 1 46.88 8.51 -4 -8 -1 42.79 7.91 4 8 -1 44.85 6.89 4 8 -2 3.99 2.44 -4 -8 2 3.10 2.22 -4 -8 -2 -1.10 2.85 4 8 -3 3.33 2.05 -4 -8 3 0.36 1.48 4 -8 -3 1.24 0.67 -4 -8 -3 -0.90 2.82 4 8 -4 5.35 2.53 -4 -8 4 7.30 3.60 4 8 -5 14.47 4.54 -4 -8 5 16.11 5.21 -4 -8 6 36.06 7.50 4 8 -6 34.99 7.07 -4 -8 7 28.52 6.91 4 8 -7 32.12 6.87 4 8 -8 2.96 2.08 -4 -8 8 3.93 2.62 4 8 -9 7.38 3.52 -4 -8 9 11.99 5.08 4 8 -10 44.53 8.47 -4 -8 10 52.51 9.36 4 8 -11 6.51 3.35 4 8 -12 3.13 2.09 4 8 -13 7.10 3.94 4 8 -14 2.39 2.49 4 8 -15 -0.68 1.64 4 8 -16 7.38 4.01 4 8 -17 0.00 0.80 -5 -8 0 20.45 5.59 5 8 0 23.99 5.11 5 8 -1 0.48 0.65 5 8 1 -0.86 1.21 -5 -8 1 -0.57 1.54 -5 -8 -1 0.05 2.47 5 8 -2 4.04 2.12 -5 -8 2 2.62 1.52 -5 -8 -2 0.90 1.06 5 8 -3 3.46 2.15 -5 -8 3 5.74 3.72 -5 -8 -3 -1.97 3.11 5 8 -4 5.64 2.82 -5 -8 4 8.81 4.22 5 8 -5 2.50 1.89 -5 -8 5 2.40 2.94 5 8 -6 7.12 2.90 -5 -8 6 7.88 3.45 5 8 -7 4.98 2.76 -5 -8 7 5.67 3.21 5 8 -8 6.89 3.19 -5 -8 8 10.35 4.61 -5 -8 9 3.87 3.12 5 8 -9 0.44 1.59 5 8 -10 -0.07 0.48 -5 -8 10 2.31 2.39 5 8 -11 1.51 1.54 5 8 -12 2.97 2.35 5 8 -13 -1.33 2.09 5 8 -14 -2.48 2.66 5 8 -15 12.13 5.08 5 8 -16 2.95 2.18 -6 -8 0 1.50 1.41 6 8 0 1.51 1.43 -6 -8 1 8.54 3.98 6 8 -1 5.61 2.59 -6 -8 -1 5.25 2.44 6 8 1 5.97 2.61 -6 -8 2 23.26 6.25 6 8 -2 24.08 5.55 -6 -8 -2 22.82 6.02 -6 -8 3 -0.95 1.40 6 8 -3 1.10 1.27 -6 -8 -3 -2.00 3.10 -6 -8 4 27.16 7.06 6 8 -4 19.51 5.17 -6 -8 -4 18.69 5.40 -6 -8 5 16.61 5.71 6 8 -5 10.04 3.96 -6 -8 6 4.24 2.40 6 8 -6 3.85 2.51 -6 -8 7 15.87 5.58 6 8 -7 15.39 4.81 6 8 -8 39.86 8.07 -6 -8 8 44.18 9.07 -6 -8 9 11.88 5.63 6 8 -9 7.61 3.60 -6 -8 10 7.22 3.97 6 8 -10 4.13 2.36 6 8 -11 10.74 4.53 6 8 -12 19.26 6.18 6 8 -13 14.40 5.64 6 8 -14 10.72 4.46 6 8 -15 4.65 3.17 6 8 -16 2.82 2.73 -7 -8 0 -1.26 1.63 7 8 0 -0.48 1.47 -7 -8 1 0.37 1.03 -7 -8 -1 -1.05 2.07 7 8 -1 -0.68 0.59 7 8 1 0.41 0.54 -7 -8 2 5.52 3.87 -7 -8 -2 1.71 2.22 7 8 -2 2.95 2.18 -7 -8 3 2.82 2.68 7 8 -3 -0.14 0.56 -7 -8 -3 -2.31 3.76 -7 -8 4 3.26 3.22 7 8 -4 1.32 1.26 -7 -8 -4 1.12 1.50 -7 -8 5 5.85 4.05 7 8 -5 3.25 2.27 -7 -8 6 6.28 3.69 7 8 -6 3.37 2.04 -7 -8 7 1.99 2.91 7 8 -7 -1.40 1.70 -7 -8 8 2.55 2.68 7 8 -8 2.93 2.49 -7 -8 9 4.13 3.90 7 8 -9 2.64 2.09 -7 -8 10 4.29 3.89 7 8 -10 2.70 2.37 7 8 -11 4.48 3.22 7 8 -12 2.44 2.53 7 8 -13 3.19 2.66 7 8 -14 2.53 2.04 7 8 -15 2.02 2.29 -8 -8 0 -1.77 2.79 -8 -8 1 16.02 5.58 -8 -8 -1 14.44 4.85 -8 -8 2 13.49 4.97 -8 -8 -2 12.06 4.53 8 8 -2 12.73 4.40 -8 -8 3 2.58 2.38 -8 -8 -3 1.88 1.08 8 8 -3 3.27 2.56 -8 -8 4 3.72 3.08 8 8 -4 4.02 2.86 -8 -8 -4 3.74 2.68 -8 -8 5 27.97 7.59 8 8 -5 23.83 6.30 -8 -8 -5 20.59 6.27 -8 -8 6 5.96 3.56 8 8 -6 5.83 3.25 -8 -8 7 5.17 3.25 8 8 -7 7.24 3.69 -8 -8 8 22.71 6.98 8 8 -8 12.12 4.63 -8 -8 9 24.30 7.43 8 8 -9 15.25 5.50 -8 -8 10 8.35 4.84 8 8 -10 2.58 2.32 8 8 -11 27.73 7.47 8 8 -12 21.06 6.85 8 8 -13 1.91 1.89 8 8 -14 3.78 3.20 -9 -8 0 0.42 0.87 -9 -8 1 -0.03 1.28 -9 -8 -1 -2.37 2.28 -9 -8 2 5.21 3.24 -9 -8 -2 1.09 2.26 -9 -8 3 3.03 2.95 -9 -8 -3 1.29 0.61 -9 -8 4 6.42 4.31 -9 -8 -4 -1.84 1.90 9 8 -4 3.06 2.78 9 8 -5 0.46 0.77 -9 -8 -5 2.43 2.65 -9 -8 6 8.34 3.71 9 8 -6 11.15 4.68 -9 -8 -6 3.82 1.85 -9 -8 7 2.25 0.67 9 8 -7 3.53 2.34 -9 -8 8 6.44 4.16 9 8 -8 1.50 1.20 -9 -8 9 2.41 3.17 9 8 -9 4.25 3.06 -9 -8 10 6.41 3.93 9 8 -10 1.19 1.33 9 8 -11 3.84 3.41 9 8 -12 1.39 1.02 9 8 -13 -0.46 0.74 -10 -8 0 6.49 3.02 -10 -8 1 8.32 4.38 -10 -8 -1 9.72 4.14 -10 -8 2 6.47 3.69 -10 -8 -2 4.15 3.00 -10 -8 3 8.80 4.74 -10 -8 -3 4.79 2.21 -10 -8 4 23.54 7.43 -10 -8 -4 16.20 5.56 -10 -8 5 26.81 7.60 -10 -8 -5 18.30 6.05 -10 -8 6 24.69 7.62 -10 -8 -6 17.55 6.02 10 8 -6 19.44 6.33 -10 -8 7 7.34 3.91 10 8 -7 2.04 2.42 -10 -8 8 12.57 5.78 10 8 -8 16.69 5.81 10 8 -9 12.32 5.24 10 8 -10 3.78 2.92 10 8 -11 10.83 5.10 -11 -8 0 -0.26 1.63 -11 -8 1 9.29 4.57 -11 -8 -1 12.81 5.67 -11 -8 2 1.98 2.39 -11 -8 -2 -0.43 2.25 -11 -8 3 4.64 3.39 -11 -8 -3 -3.24 3.66 -11 -8 4 5.05 3.72 -11 -8 -4 -0.74 1.24 11 8 -7 0.92 1.85 11 8 -8 2.35 2.64 11 8 -9 -0.44 0.66 0 -9 0 -0.25 0.93 0 -9 1 1.47 2.49 0 -9 -1 1.23 1.54 0 -9 2 1.68 2.26 0 -9 -2 0.46 1.44 0 -9 3 11.50 4.26 0 -9 -3 9.89 3.50 0 -9 4 -0.19 0.87 0 -9 -4 -1.65 2.00 0 -9 5 3.22 2.50 0 -9 6 1.50 2.01 0 9 -6 -0.66 1.93 0 -9 7 5.69 3.58 0 9 -7 0.28 0.86 0 9 -8 -2.21 2.03 0 9 -9 6.36 3.25 0 9 -10 -4.64 3.13 0 9 -11 5.04 2.90 0 9 -12 -3.75 3.45 0 9 -13 -2.00 2.28 0 9 -14 -1.17 2.21 0 9 -15 1.66 1.32 0 9 -16 -0.78 1.97 1 -9 0 18.21 4.79 -1 -9 0 25.08 6.07 1 -9 1 5.16 2.70 -1 -9 1 4.21 2.44 1 -9 -1 3.42 2.63 -1 -9 -1 3.36 2.00 1 -9 2 12.85 4.31 -1 -9 2 13.02 4.44 1 -9 -2 12.04 3.81 -1 -9 -2 14.85 4.45 1 -9 3 26.38 5.82 -1 -9 3 28.23 6.64 1 -9 -3 22.12 5.37 -1 -9 -3 18.88 5.03 1 -9 4 16.99 4.75 -1 -9 4 19.40 5.43 1 -9 -4 17.88 4.80 -1 -9 -4 18.24 5.02 1 -9 5 3.51 2.64 -1 -9 5 3.08 2.42 -1 -9 6 31.96 6.89 1 9 -6 27.47 6.13 1 -9 6 33.88 6.95 -1 -9 7 21.16 5.73 -1 9 -7 17.24 4.73 1 9 -7 18.59 5.22 1 -9 7 23.40 5.71 -1 -9 8 1.66 1.91 -1 9 -8 1.27 1.05 1 9 -8 1.30 1.60 -1 9 -9 6.53 2.95 1 9 -9 7.10 3.40 -1 9 -10 14.38 4.60 1 9 -10 17.81 5.29 -1 9 -11 0.90 0.94 1 9 -11 5.67 3.38 -1 9 -12 2.80 2.02 1 9 -12 4.87 2.75 -1 9 -13 10.02 4.37 1 9 -13 10.94 4.40 -1 9 -14 3.92 3.07 1 9 -14 4.90 3.03 -1 9 -15 5.03 3.29 1 9 -15 2.03 2.24 -1 9 -16 9.25 4.44 1 9 -16 7.89 4.16 2 -9 0 4.93 2.39 -2 -9 0 4.00 2.33 2 -9 1 2.15 2.08 -2 -9 1 2.92 2.02 2 -9 -1 2.14 1.71 -2 -9 -1 -1.96 2.96 2 -9 2 3.23 2.14 -2 -9 2 4.70 2.62 2 -9 -2 2.27 1.76 -2 -9 -2 1.23 1.39 -2 -9 3 12.23 4.70 2 -9 -3 5.97 2.72 -2 -9 -3 4.99 2.55 -2 -9 4 10.63 4.59 2 -9 -4 0.79 1.05 -2 -9 -4 6.24 3.04 -2 -9 5 2.68 2.39 2 9 -5 3.38 2.04 -2 -9 6 10.04 4.56 2 9 -6 5.24 2.78 -2 -9 7 1.02 2.74 -2 9 -7 0.16 1.05 2 9 -7 -0.14 0.77 -2 -9 8 3.28 2.87 -2 9 -8 0.64 1.36 2 9 -8 1.90 1.51 -2 9 -9 -0.98 1.63 2 9 -9 0.48 1.36 -2 -9 9 2.30 2.64 -2 9 -10 3.84 2.38 2 9 -10 4.24 2.70 -2 9 -11 1.04 0.44 2 9 -11 0.96 1.28 -2 9 -12 1.64 2.03 2 9 -12 0.75 1.32 -2 9 -13 1.46 1.20 2 9 -13 1.04 1.58 -2 9 -14 1.66 1.72 2 9 -14 2.22 1.89 -2 9 -15 -0.11 1.73 2 9 -15 2.86 2.41 -2 9 -16 0.02 0.50 -3 -9 0 15.61 4.96 -3 -9 1 30.68 7.20 -3 -9 -1 26.36 6.43 -3 -9 2 12.88 4.52 -3 -9 -2 11.40 3.96 -3 -9 3 32.64 7.46 -3 -9 -3 32.81 7.19 -3 -9 4 34.29 7.73 -3 -9 -4 28.17 6.67 -3 -9 5 15.41 5.06 3 9 -5 16.82 4.89 -3 -9 6 21.22 5.94 3 9 -6 20.94 5.55 -3 -9 7 19.26 6.03 3 9 -7 16.84 5.30 -3 -9 8 14.46 5.48 3 9 -8 9.62 3.91 -3 -9 9 32.43 7.90 3 9 -9 23.93 6.20 3 9 -10 8.07 3.64 3 9 -11 3.60 2.61 -3 9 -12 1.79 1.92 3 9 -12 2.75 2.31 -3 9 -13 6.88 3.78 3 9 -13 5.34 3.59 -3 9 -14 1.94 1.78 3 9 -14 3.39 2.82 -3 9 -15 5.09 3.31 3 9 -15 3.27 2.99 -3 9 -16 2.65 2.51 -4 -9 0 11.56 4.61 -4 -9 1 9.05 4.41 -4 -9 -1 0.99 1.07 -4 -9 2 4.44 2.94 -4 -9 -2 -2.89 1.91 -4 -9 3 6.69 4.03 -4 -9 -3 0.05 1.42 -4 -9 4 7.88 3.66 -4 -9 -4 0.27 2.04 4 9 -5 1.54 1.37 -4 -9 5 1.02 1.38 4 9 -6 0.64 1.19 -4 -9 6 3.23 2.92 4 9 -7 3.95 2.66 -4 -9 7 -0.20 1.35 4 9 -8 8.25 3.59 -4 -9 8 12.04 4.66 -4 -9 9 6.65 4.07 4 9 -9 2.74 2.12 4 9 -10 1.17 2.25 4 9 -11 -0.65 0.69 4 9 -12 8.50 4.56 4 9 -13 5.19 3.57 4 9 -14 1.62 0.76 4 9 -15 1.24 0.72 -5 -9 0 11.18 4.82 -5 -9 1 36.32 8.02 -5 -9 -1 37.65 8.20 -5 -9 2 4.93 2.83 -5 -9 -2 4.11 3.19 -5 -9 3 0.17 1.80 -5 -9 -3 -1.28 2.31 5 9 -4 13.07 4.54 -5 -9 4 14.53 5.31 -5 -9 -4 7.72 3.55 -5 -9 5 31.25 7.77 -5 -9 -5 34.60 8.02 5 9 -5 28.58 6.58 5 9 -6 6.85 3.60 -5 -9 6 6.87 3.88 5 9 -7 22.66 6.31 -5 -9 7 26.17 6.99 5 9 -8 7.89 3.91 -5 -9 8 14.78 5.54 5 9 -9 14.89 5.26 -5 -9 9 10.57 4.60 5 9 -10 12.93 4.98 -5 -9 10 18.17 6.05 5 9 -11 14.86 5.38 5 9 -12 8.11 4.07 5 9 -13 1.95 2.07 5 9 -14 3.26 2.43 -6 -9 0 0.96 1.03 -6 -9 1 4.28 2.86 -6 -9 -1 5.04 2.63 -6 -9 2 -1.55 2.57 -6 -9 -2 1.93 2.19 -6 -9 3 2.41 2.50 -6 -9 -3 0.11 1.12 6 9 -4 1.83 1.61 -6 -9 4 1.92 3.00 -6 -9 -4 -1.47 2.98 6 9 -5 2.88 1.95 -6 -9 5 5.83 3.25 -6 -9 -5 0.24 2.13 6 9 -6 5.11 2.67 -6 -9 6 5.47 3.69 6 9 -7 2.45 2.26 -6 -9 7 3.37 2.89 6 9 -8 -3.28 2.59 -6 -9 8 5.92 3.86 6 9 -9 1.96 2.29 -6 -9 9 3.05 2.51 6 9 -10 2.50 1.95 -6 -9 10 1.87 2.33 6 9 -11 0.36 1.29 6 9 -12 5.95 3.49 6 9 -13 -1.77 2.63 -7 -9 0 2.31 2.56 -7 -9 1 -1.46 1.93 -7 -9 -1 1.02 1.58 -7 -9 2 33.97 8.73 -7 -9 -2 32.63 8.09 -7 -9 3 3.60 3.70 -7 -9 -3 0.19 1.53 -7 -9 4 24.95 7.56 7 9 -4 12.71 4.46 -7 -9 -4 14.34 5.26 -7 -9 5 1.21 1.85 7 9 -5 4.07 2.67 -7 -9 -5 3.91 3.23 -7 -9 6 16.41 5.92 7 9 -6 11.92 4.49 -7 -9 -6 8.87 4.17 -7 -9 7 0.23 2.97 7 9 -7 1.38 2.37 7 9 -8 52.09 9.92 -7 -9 8 49.51 10.51 -7 -9 9 4.67 3.49 7 9 -9 4.27 3.06 7 9 -10 2.22 2.27 -7 -9 10 6.94 4.47 7 9 -11 6.02 3.81 7 9 -12 29.04 7.97 -8 -9 0 0.20 1.36 -8 -9 1 1.13 1.77 -8 -9 -1 2.48 1.74 -8 -9 2 9.26 4.94 -8 -9 -2 1.88 2.36 -8 -9 3 1.63 2.58 -8 -9 -3 0.27 1.17 -8 -9 4 0.45 1.39 8 9 -4 2.77 2.16 -8 -9 -4 1.43 1.66 -8 -9 5 6.70 3.86 8 9 -5 6.55 3.44 -8 -9 -5 3.89 3.15 -8 -9 6 3.43 3.26 8 9 -6 2.56 2.27 -8 -9 -6 0.68 0.69 -8 -9 7 3.88 2.91 8 9 -7 -0.92 1.55 8 9 -8 2.67 2.16 8 9 -9 0.29 1.67 8 9 -10 4.75 3.31 8 9 -11 2.25 2.59 -9 -9 0 18.30 6.36 -9 -9 1 14.88 5.81 9 9 -4 4.07 2.79 9 9 -5 29.13 7.45 9 9 -6 8.89 4.35 9 9 -7 5.67 3.74 9 9 -8 3.37 3.19 9 9 -9 10.09 4.78 9 9 -10 18.94 6.86 10 9 -4 4.76 3.47 10 9 -5 0.76 1.82 10 9 -6 1.10 2.02 10 9 -7 0.16 1.42 10 9 -8 0.66 1.93 11 9 -4 3.17 2.84 11 9 -5 4.15 3.12 11 9 -6 2.60 2.89 0 -10 0 37.43 7.73 0 -10 1 2.69 2.71 0 -10 -1 0.32 1.18 0 -10 2 8.07 3.66 0 -10 -2 7.12 3.01 0 -10 3 -1.88 2.02 0 -10 -3 -1.24 2.32 0 -10 4 11.02 4.24 0 -10 -4 13.00 4.72 0 -10 -5 0.21 1.30 0 -10 -6 19.31 5.74 0 10 -13 -1.03 1.86 -1 -10 0 3.54 2.26 -1 -10 1 2.21 2.39 -1 -10 -1 1.24 2.21 -1 -10 2 7.43 3.89 -1 -10 -2 3.23 2.41 -1 -10 3 3.24 2.59 -1 -10 -3 4.91 3.36 -1 -10 4 8.71 4.17 -1 -10 -4 9.14 3.80 -1 -10 5 0.19 0.77 -1 -10 -5 0.47 1.47 -1 -10 6 17.34 5.63 -1 -10 -6 8.48 4.04 -1 -10 7 7.94 4.22 1 10 -12 5.58 3.26 -1 10 -13 4.53 3.31 1 10 -13 4.29 3.18 -2 -10 0 4.53 3.27 -2 -10 1 2.90 2.88 -2 -10 -1 -0.94 1.64 -2 -10 2 11.77 4.72 -2 -10 -2 5.16 2.68 -2 -10 3 11.06 5.05 -2 -10 -3 9.08 3.97 -2 -10 4 5.08 3.20 -2 -10 -4 6.27 3.51 -2 -10 5 -0.71 1.30 -2 -10 -5 -3.26 3.04 -2 -10 6 3.52 3.43 -2 -10 -6 2.29 2.46 -2 -10 7 21.92 6.49 -2 -10 8 7.50 4.23 2 10 -12 1.57 2.00 2 10 -13 6.33 4.06 -3 -10 0 0.23 1.51 -3 -10 1 1.22 1.20 -3 -10 -1 1.25 1.31 -3 -10 2 12.42 5.17 -3 -10 -2 8.49 3.78 -3 -10 3 30.80 7.84 -3 -10 -3 27.42 7.11 -3 -10 4 17.14 5.90 -3 -10 -4 12.52 5.02 -3 -10 5 12.30 4.93 -3 -10 -5 4.87 2.88 -3 -10 6 4.29 2.94 -3 -10 -6 -2.40 1.92 -3 -10 7 3.01 2.51 -3 -10 8 9.05 4.43 3 10 -11 7.01 3.83 3 10 -12 2.72 2.84 -4 -10 0 12.84 5.16 -4 -10 1 11.21 4.98 -4 -10 -1 0.97 1.18 -4 -10 2 0.83 1.31 -4 -10 -2 0.60 1.28 -4 -10 3 3.87 3.52 -4 -10 -3 0.46 0.94 -4 -10 4 8.64 4.49 -4 -10 -4 9.62 4.41 -4 -10 5 10.72 4.62 -4 -10 -5 7.84 3.86 -4 -10 6 6.54 3.69 -4 -10 -6 3.75 3.13 -4 -10 7 5.02 3.52 -4 -10 -7 1.92 1.89 -4 -10 8 3.54 2.77 -4 -10 9 15.28 5.59 4 10 -11 5.30 3.48 4 10 -12 1.79 2.51 -5 -10 0 2.53 2.86 -5 -10 1 10.00 4.73 -5 -10 -1 4.77 3.30 -5 -10 2 4.10 3.22 -5 -10 -2 3.18 2.21 -5 -10 3 4.28 3.60 -5 -10 -3 2.29 2.45 -5 -10 4 1.41 1.74 -5 -10 -4 2.19 1.56 -5 -10 5 1.15 1.47 -5 -10 -5 0.75 1.40 -5 -10 6 4.16 4.09 -5 -10 -6 1.26 1.39 -5 -10 7 2.91 2.90 -5 -10 8 1.35 1.96 5 10 -11 -0.43 1.92 -6 -10 0 0.28 1.58 -6 -10 1 4.52 3.21 -6 -10 -1 -1.18 2.36 -6 -10 2 8.12 3.84 -6 -10 -2 8.01 3.78 -6 -10 3 5.77 4.04 -6 -10 4 6.72 3.95 -2 -11 0 -0.19 1.55 -2 -11 1 2.92 2.98 -2 -11 -1 5.27 3.36 -2 -11 2 -1.44 1.75 -2 -11 -2 0.01 1.22 -2 -11 3 0.36 0.82 -2 -11 -3 -1.52 1.79 -2 -11 -4 0.36 1.32 -2 -11 -5 -1.59 2.66 -3 -11 0 3.21 2.91 -3 -11 1 4.20 3.46 -3 -11 -1 1.50 2.12 -3 -11 2 1.40 2.16 -3 -11 3 0.53 1.57 TITL smz_f1_rt2 in Pnma REM Pnma (#62, found as Pbnm in bca setting) CELL 0.71073 14.490238 22.010572 8.224880 90.0000 90.0000 90.0000 ZERR 7.00 0.000854 0.001428 0.000571 0.0000 0.0000 0.0000 LATT 1 SYMM -x+1/2,-y, z+1/2 SYMM -x, y+1/2,-z SYMM x+1/2,-y+1/2,-z+1/2 SFAC C H N O S UNIT 105.00 105.00 21.00 14.00 7.00 TREF HKLF 4 END _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' ; _shelx_hkl_checksum 41469