data_smz_f1_150_a _audit_creation_method SHELXL-97 _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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_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 14.4393(7) _cell_length_b 8.1764(4) _cell_length_c 21.7395(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2566.6(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8842 _exptl_absorpt_correction_T_max 0.9513 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8420 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 29.07 _reflns_number_total 4192 _reflns_number_gt 3341 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(9) _refine_ls_number_reflns 4192 _refine_ls_number_parameters 343 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.64354(5) 0.49436(9) 0.34343(4) 0.01954(19) Uani 1 1 d . . . S2 S 0.57820(5) 0.49857(10) 0.65338(5) 0.01872(19) Uani 1 1 d . . . O1 O 0.68657(15) 0.3695(3) 0.30747(12) 0.0260(6) Uani 1 1 d . . . O2 O 0.54606(14) 0.5218(3) 0.33711(12) 0.0255(5) Uani 1 1 d . . . O3 O 0.67585(14) 0.4711(3) 0.65984(13) 0.0244(5) Uani 1 1 d . . . O4 O 0.53577(14) 0.6256(3) 0.68895(12) 0.0246(6) Uani 1 1 d . . . N1 N 0.8407(2) 1.1170(3) 0.31257(17) 0.0295(7) Uani 1 1 d D . . N2 N 0.65281(18) 0.4463(4) 0.41725(15) 0.0215(7) Uani 1 1 d D . . N3 N 0.81265(18) 0.4078(3) 0.41640(14) 0.0218(6) Uani 1 1 d . . . N4 N 0.7274(2) 0.4318(4) 0.50975(15) 0.0320(8) Uani 1 1 d . . . N5 N 0.3802(2) -0.1205(3) 0.69460(16) 0.0373(8) Uani 1 1 d . . . H5A H 0.3238 -0.1196 0.7073 0.049 Uiso 1 1 calc R . . H5B H 0.4076 -0.2121 0.6876 0.049 Uiso 1 1 calc R . . N6 N 0.56791(18) 0.5428(4) 0.57988(14) 0.0231(7) Uani 1 1 d D . . N7 N 0.40951(19) 0.5878(3) 0.58098(14) 0.0236(7) Uani 1 1 d . . . N8 N 0.4945(2) 0.5652(4) 0.48739(15) 0.0325(8) Uani 1 1 d . . . C1 C 0.7021(2) 0.6770(4) 0.33375(19) 0.0192(8) Uani 1 1 d . . . C2 C 0.7923(2) 0.6795(4) 0.31027(16) 0.0186(7) Uani 1 1 d . . . H2 H 0.8213 0.5821 0.2996 0.024 Uiso 1 1 calc R . . C3 C 0.8378(2) 0.8250(4) 0.30289(19) 0.0195(8) Uani 1 1 d . . . H3 H 0.8978 0.8256 0.2873 0.025 Uiso 1 1 calc R . . C4 C 0.7951(2) 0.9732(4) 0.31861(16) 0.0195(7) Uani 1 1 d . . . C5 C 0.7044(2) 0.9696(4) 0.3424(2) 0.0240(8) Uani 1 1 d . . . H5 H 0.6749 1.0668 0.3530 0.031 Uiso 1 1 calc R . . C6 C 0.6593(2) 0.8233(4) 0.35014(18) 0.0213(8) Uani 1 1 d . . . H6 H 0.5997 0.8218 0.3664 0.028 Uiso 1 1 calc R . . C7 C 0.7356(2) 0.4284(4) 0.44866(17) 0.0216(8) Uani 1 1 d . . . C8 C 0.8058(3) 0.4074(6) 0.5410(2) 0.0472(12) Uani 1 1 d . . . H8 H 0.8037 0.4045 0.5837 0.061 Uiso 1 1 calc R . . C9 C 0.8896(3) 0.3864(6) 0.5120(2) 0.0424(11) Uani 1 1 d . . . H9 H 0.9436 0.3716 0.5346 0.055 Uiso 1 1 calc R . . C10 C 0.8914(2) 0.3878(4) 0.4490(2) 0.0293(9) Uani 1 1 d . . . C11 C 0.9778(2) 0.3669(5) 0.4129(2) 0.0381(10) Uani 1 1 d . . . H11A H 0.9817 0.2563 0.3982 0.049 Uiso 1 1 calc R . . H11B H 1.0303 0.3901 0.4385 0.049 Uiso 1 1 calc R . . H11C H 0.9773 0.4406 0.3785 0.049 Uiso 1 1 calc R . . C12 C 0.5190(2) 0.3170(4) 0.66629(16) 0.0181(7) Uani 1 1 d . . . C13 C 0.5635(2) 0.1698(4) 0.6551(2) 0.0246(8) Uani 1 1 d . . . H13 H 0.6243 0.1696 0.6411 0.032 Uiso 1 1 calc R . . C14 C 0.5181(2) 0.0238(4) 0.66470(18) 0.0261(9) Uani 1 1 d . . . H14 H 0.5486 -0.0745 0.6573 0.034 Uiso 1 1 calc R . . C15 C 0.4261(2) 0.0228(4) 0.68558(17) 0.0234(8) Uani 1 1 d . . . C16 C 0.3821(2) 0.1728(4) 0.69684(17) 0.0218(8) Uani 1 1 d . . . H16 H 0.3214 0.1742 0.7112 0.028 Uiso 1 1 calc R . . C17 C 0.4283(2) 0.3189(4) 0.68676(19) 0.0215(9) Uani 1 1 d . . . H17 H 0.3984 0.4179 0.6937 0.028 Uiso 1 1 calc R . . C18 C 0.4861(2) 0.5676(4) 0.54838(17) 0.0222(8) Uani 1 1 d . . . C19 C 0.4164(3) 0.5940(6) 0.4568(2) 0.0456(12) Uani 1 1 d . . . H19 H 0.4183 0.5954 0.4140 0.059 Uiso 1 1 calc R . . C20 C 0.3332(3) 0.6217(6) 0.4854(2) 0.0469(12) Uani 1 1 d . . . H20 H 0.2799 0.6444 0.4629 0.061 Uiso 1 1 calc R . . C21 C 0.3313(2) 0.6147(5) 0.54896(19) 0.0291(9) Uani 1 1 d . . . C22 C 0.2451(2) 0.6367(5) 0.5861(2) 0.0401(10) Uani 1 1 d . . . H22A H 0.1922 0.6330 0.5594 0.052 Uiso 1 1 calc R . . H22B H 0.2471 0.7404 0.6067 0.052 Uiso 1 1 calc R . . H22C H 0.2407 0.5506 0.6160 0.052 Uiso 1 1 calc R . . H1N1 H 0.8925(15) 1.124(4) 0.2936(15) 0.026(9) Uiso 1 1 d D . . H2N1 H 0.8085(19) 1.205(3) 0.3175(16) 0.032(10) Uiso 1 1 d D . . H1N2 H 0.6084(19) 0.478(4) 0.4412(16) 0.029(11) Uiso 1 1 d D . . H1N6 H 0.619(2) 0.508(5) 0.561(2) 0.059(15) 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 0.0183(4) 0.0213(4) 0.0190(5) 0.0019(4) -0.0012(4) -0.0015(3) S2 0.0181(4) 0.0207(4) 0.0175(5) 0.0025(4) -0.0007(4) -0.0014(3) O1 0.0303(12) 0.0219(12) 0.0258(15) -0.0024(11) 0.0005(12) -0.0019(10) O2 0.0196(11) 0.0331(12) 0.0237(15) 0.0037(12) -0.0047(12) -0.0020(9) O3 0.0165(11) 0.0333(13) 0.0233(14) 0.0030(12) -0.0029(11) -0.0031(9) O4 0.0249(12) 0.0213(12) 0.0276(16) -0.0020(10) -0.0028(12) 0.0002(9) N1 0.0235(16) 0.0226(14) 0.042(2) -0.0049(14) 0.0125(16) -0.0001(12) N2 0.0138(14) 0.0328(16) 0.0180(18) 0.0056(13) -0.0010(13) 0.0009(11) N3 0.0193(14) 0.0257(15) 0.0205(18) 0.0002(12) 0.0004(14) 0.0023(12) N4 0.0224(16) 0.053(2) 0.021(2) 0.0024(16) -0.0028(15) 0.0106(15) N5 0.0321(16) 0.0213(14) 0.059(2) -0.0023(15) 0.0124(17) -0.0051(12) N6 0.0169(14) 0.0339(16) 0.0184(19) 0.0059(13) 0.0028(14) 0.0023(12) N7 0.0212(15) 0.0245(15) 0.025(2) -0.0001(13) 0.0037(14) -0.0006(12) N8 0.0250(16) 0.0512(19) 0.021(2) 0.0052(15) -0.0022(15) 0.0105(15) C1 0.0206(17) 0.0214(15) 0.015(2) 0.0010(15) 0.0005(16) 0.0002(13) C2 0.0198(16) 0.0237(16) 0.0123(19) 0.0005(14) -0.0025(15) 0.0055(12) C3 0.0157(16) 0.0295(19) 0.013(2) -0.0026(16) 0.0011(15) 0.0002(13) C4 0.0192(15) 0.0250(16) 0.0144(18) -0.0010(13) -0.0016(14) -0.0018(13) C5 0.0229(16) 0.0225(17) 0.027(2) -0.0006(17) 0.005(2) 0.0029(13) C6 0.0174(15) 0.0267(16) 0.020(2) 0.0016(16) 0.0064(16) 0.0033(12) C7 0.0200(17) 0.0205(16) 0.024(2) 0.0041(14) -0.0018(17) 0.0008(13) C8 0.036(2) 0.082(3) 0.024(3) -0.002(2) -0.007(2) 0.017(2) C9 0.0212(19) 0.079(3) 0.027(3) -0.005(2) -0.010(2) 0.0155(19) C10 0.0215(18) 0.0321(19) 0.034(3) -0.0052(17) -0.0003(18) 0.0036(15) C11 0.024(2) 0.048(2) 0.042(3) -0.006(2) 0.001(2) 0.0048(16) C12 0.0198(15) 0.0201(14) 0.014(2) 0.0020(13) 0.0002(15) -0.0025(12) C13 0.0183(17) 0.0244(16) 0.031(2) -0.0004(18) 0.0052(19) 0.0006(13) C14 0.0255(16) 0.0185(16) 0.034(3) -0.0030(15) 0.0026(17) 0.0036(13) C15 0.0257(18) 0.0230(17) 0.021(2) -0.0006(14) 0.0017(16) -0.0003(13) C16 0.0207(17) 0.0238(16) 0.021(2) 0.0002(15) 0.0015(15) -0.0015(12) C17 0.0208(18) 0.0196(17) 0.024(2) -0.0028(15) 0.0007(17) 0.0037(13) C18 0.0180(17) 0.0259(16) 0.023(2) 0.0027(15) -0.0022(16) 0.0012(13) C19 0.032(2) 0.082(3) 0.023(3) -0.001(2) -0.005(2) 0.019(2) C20 0.026(2) 0.077(3) 0.038(3) -0.003(2) -0.010(2) 0.021(2) C21 0.0214(18) 0.0340(19) 0.032(3) -0.0030(17) -0.0015(18) 0.0053(15) C22 0.0212(18) 0.049(2) 0.050(3) -0.005(2) 0.000(2) 0.0066(17) _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 1.428(2) . ? S1 O2 1.432(2) . ? S1 N2 1.658(3) . ? S1 C1 1.729(3) . ? S2 O4 1.433(2) . ? S2 O3 1.435(2) . ? S2 N6 1.645(3) . ? S2 C12 1.736(3) . ? N1 C4 1.355(4) . ? N1 H1N1 0.855(18) . ? N1 H2N1 0.861(18) . ? N2 C7 1.385(4) . ? N2 H1N2 0.865(18) . ? N3 C7 1.326(4) . ? N3 C10 1.350(4) . ? N4 C7 1.334(5) . ? N4 C8 1.336(5) . ? N5 C15 1.361(4) . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? N6 C18 1.380(4) . ? N6 H1N6 0.898(19) . ? N7 C18 1.324(4) . ? N7 C21 1.344(5) . ? N8 C19 1.331(5) . ? N8 C18 1.332(5) . ? C1 C6 1.393(5) . ? C1 C2 1.399(4) . ? C2 C3 1.369(5) . ? C2 H2 0.9300 . ? C3 C4 1.402(4) . ? C3 H3 0.9300 . ? C4 C5 1.409(4) . ? C5 C6 1.372(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.374(5) . ? C8 H8 0.9300 . ? C9 C10 1.370(6) . ? C9 H9 0.9300 . ? C10 C11 1.483(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C17 1.383(4) . ? C12 C13 1.386(4) . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.405(4) . ? C14 H14 0.9300 . ? C15 C16 1.403(4) . ? C16 C17 1.386(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C19 C20 1.373(5) . ? C19 H19 0.9300 . ? C20 C21 1.382(6) . ? C20 H20 0.9300 . ? C21 C22 1.494(5) . ? 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 119.15(15) . . ? O1 S1 N2 108.97(16) . . ? O2 S1 N2 102.09(15) . . ? O1 S1 C1 109.76(16) . . ? O2 S1 C1 109.50(14) . . ? N2 S1 C1 106.46(18) . . ? O4 S2 O3 118.76(15) . . ? O4 S2 N6 109.04(15) . . ? O3 S2 N6 102.60(15) . . ? O4 S2 C12 108.79(16) . . ? O3 S2 C12 109.54(15) . . ? N6 S2 C12 107.48(16) . . ? C4 N1 H1N1 122(2) . . ? C4 N1 H2N1 117(2) . . ? H1N1 N1 H2N1 119(3) . . ? C7 N2 S1 124.9(2) . . ? C7 N2 H1N2 112(3) . . ? S1 N2 H1N2 117(3) . . ? C7 N3 C10 116.4(3) . . ? C7 N4 C8 115.3(3) . . ? C15 N5 H5A 120.0 . . ? C15 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C18 N6 S2 126.3(2) . . ? C18 N6 H1N6 122(3) . . ? S2 N6 H1N6 108(3) . . ? C18 N7 C21 116.4(3) . . ? C19 N8 C18 114.7(3) . . ? C6 C1 C2 119.6(3) . . ? C6 C1 S1 119.6(2) . . ? C2 C1 S1 120.8(2) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? N1 C4 C3 120.8(3) . . ? N1 C4 C5 120.4(3) . . ? C3 C4 C5 118.8(3) . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 120.5(3) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? N3 C7 N4 127.2(3) . . ? N3 C7 N2 118.5(3) . . ? N4 C7 N2 114.3(3) . . ? N4 C8 C9 122.1(4) . . ? N4 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? C10 C9 C8 118.3(4) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? N3 C10 C9 120.6(3) . . ? N3 C10 C11 116.4(4) . . ? C9 C10 C11 123.0(4) . . ? 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 . . ? C17 C12 C13 120.3(3) . . ? C17 C12 S2 120.6(2) . . ? C13 C12 S2 119.1(2) . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? N5 C15 C16 120.5(3) . . ? N5 C15 C14 120.8(3) . . ? C16 C15 C14 118.7(3) . . ? C17 C16 C15 120.5(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C12 C17 C16 119.8(3) . . ? C12 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? N7 C18 N8 127.7(3) . . ? N7 C18 N6 117.9(3) . . ? N8 C18 N6 114.4(3) . . ? N8 C19 C20 123.0(4) . . ? N8 C19 H19 118.5 . . ? C20 C19 H19 118.5 . . ? C19 C20 C21 117.6(4) . . ? C19 C20 H20 121.2 . . ? C21 C20 H20 121.2 . . ? N7 C21 C20 120.5(3) . . ? N7 C21 C22 116.1(4) . . ? C20 C21 C22 123.4(4) . . ? 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 61.8(3) . . . . ? O2 S1 N2 C7 -171.3(3) . . . . ? C1 S1 N2 C7 -56.6(3) . . . . ? O4 S2 N6 C18 -58.5(3) . . . . ? O3 S2 N6 C18 174.7(3) . . . . ? C12 S2 N6 C18 59.2(3) . . . . ? O1 S1 C1 C6 162.4(3) . . . . ? O2 S1 C1 C6 29.9(4) . . . . ? N2 S1 C1 C6 -79.8(3) . . . . ? O1 S1 C1 C2 -18.2(4) . . . . ? O2 S1 C1 C2 -150.8(3) . . . . ? N2 S1 C1 C2 99.6(3) . . . . ? C6 C1 C2 C3 -0.6(5) . . . . ? S1 C1 C2 C3 -180.0(3) . . . . ? C1 C2 C3 C4 -0.1(5) . . . . ? C2 C3 C4 N1 178.6(3) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? N1 C4 C5 C6 -178.1(4) . . . . ? C3 C4 C5 C6 0.2(6) . . . . ? C4 C5 C6 C1 -0.9(6) . . . . ? C2 C1 C6 C5 1.1(6) . . . . ? S1 C1 C6 C5 -179.6(3) . . . . ? C10 N3 C7 N4 0.1(5) . . . . ? C10 N3 C7 N2 -178.8(3) . . . . ? C8 N4 C7 N3 -1.8(5) . . . . ? C8 N4 C7 N2 177.1(4) . . . . ? S1 N2 C7 N3 -17.6(4) . . . . ? S1 N2 C7 N4 163.4(3) . . . . ? C7 N4 C8 C9 2.3(6) . . . . ? N4 C8 C9 C10 -1.2(7) . . . . ? C7 N3 C10 C9 1.2(5) . . . . ? C7 N3 C10 C11 -179.2(3) . . . . ? C8 C9 C10 N3 -0.6(6) . . . . ? C8 C9 C10 C11 179.8(4) . . . . ? O4 S2 C12 C17 22.9(4) . . . . ? O3 S2 C12 C17 154.2(3) . . . . ? N6 S2 C12 C17 -95.0(3) . . . . ? O4 S2 C12 C13 -157.8(3) . . . . ? O3 S2 C12 C13 -26.5(3) . . . . ? N6 S2 C12 C13 84.3(3) . . . . ? C17 C12 C13 C14 -0.4(6) . . . . ? S2 C12 C13 C14 -179.7(3) . . . . ? C12 C13 C14 C15 0.3(6) . . . . ? C13 C14 C15 N5 179.3(4) . . . . ? C13 C14 C15 C16 -0.5(6) . . . . ? N5 C15 C16 C17 -179.0(3) . . . . ? C14 C15 C16 C17 0.8(5) . . . . ? C13 C12 C17 C16 0.7(6) . . . . ? S2 C12 C17 C16 -180.0(3) . . . . ? C15 C16 C17 C12 -0.9(5) . . . . ? C21 N7 C18 N8 -2.5(5) . . . . ? C21 N7 C18 N6 178.8(3) . . . . ? C19 N8 C18 N7 3.2(6) . . . . ? C19 N8 C18 N6 -178.1(3) . . . . ? S2 N6 C18 N7 13.2(5) . . . . ? S2 N6 C18 N8 -165.6(3) . . . . ? C18 N8 C19 C20 -0.9(6) . . . . ? N8 C19 C20 C21 -1.7(7) . . . . ? C18 N7 C21 C20 -0.5(5) . . . . ? C18 N7 C21 C22 179.8(3) . . . . ? C19 C20 C21 N7 2.5(7) . . . . ? C19 C20 C21 C22 -177.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.877 _diffrn_reflns_theta_full 29.07 _diffrn_measured_fraction_theta_full 0.877 _refine_diff_density_max 0.286 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.077