data_195k_smz-f2_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 orthorhombic _symmetry_space_group_name_H-M Pbca _space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.1070(3) _cell_length_b 11.5902(3) _cell_length_c 22.8593(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2412.84(12) _cell_formula_units_Z 8 _cell_measurement_temperature 195 _cell_measurement_reflns_used 2359 _cell_measurement_theta_min 3.2550 _cell_measurement_theta_max 29.3520 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _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 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.268 _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.93262 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 195 _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type 'Synchrotron' _diffrn_radiation_source 'Diamond Light Source Beamline I19' _diffrn_radiation_monochromator 'double crystal Silicon 111' _diffrn_measurement_specimen_support 'MiTeGen loop' _diffrn_measurement_device 'CrystalLogic Kappa (3 circle)' _diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)' _diffrn_measurement_method ; omega rotation with 1 degree frames ; _diffrn_reflns_number 6243 _diffrn_reflns_av_R_equivalents 0.0600 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 2 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 29.4723 _diffrn_orient_matrix_UB_11 0.0160755000 _diffrn_orient_matrix_UB_12 -0.0448817000 _diffrn_orient_matrix_UB_21 0.0295456000 _diffrn_orient_matrix_UB_22 -0.0306691000 _diffrn_orient_matrix_UB_23 0.0229734000 _diffrn_orient_matrix_UB_31 -0.0677578000 _diffrn_orient_matrix_UB_32 -0.0240205000 _diffrn_orient_matrix_UB_33 0.0056190000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -60.00 60.00 1.0000 0.4000 omega____ theta____ kappa____ phi______ frames - 30.0000 0.0000 0.0000 120 ; _reflns_number_total 3369 _reflns_number_gt 2265 _reflns_threshold_expression >2sigma(I) _computing_structure_solution ; SHELXS-97, Sheldrick, G.M. (2008) Acta Crystallogr.,D64,112-122 ; _computing_structure_refinement ; SHELXL-97/2, G.M. Sheldrick, G.M. (2008) Acta Crystallogr.,D64,112-122 ; _computing_molecular_graphics ; ORTEX, McArdle, P. (1995) J.Appl.Cryst.,28,65-65 ; _computing_publication_material ; Ciftab, G.M. Sheldrick, G.M. (2008) Acta Crystallogr.,D64,112-122 ; _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^)+(0.0463P)^2^+1.4827P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3369 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1578 _refine_ls_wR_factor_gt 0.1359 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.33187(8) 0.34610(5) 0.38965(3) 0.02542(18) Uani 1 1 d . . . O2 O 0.1966(2) 0.39705(17) 0.40959(9) 0.0313(5) Uani 1 1 d . . . O1 O 0.3416(2) 0.22338(15) 0.38635(9) 0.0340(5) Uani 1 1 d . . . N4 N 0.6664(3) 0.42628(19) 0.48537(10) 0.0290(5) Uani 1 1 d . . . N3 N 0.6555(3) 0.28498(18) 0.40864(11) 0.0300(5) Uani 1 1 d . . . N2 N 0.4516(3) 0.39487(19) 0.43722(11) 0.0287(5) Uani 1 1 d . . . N1 N 0.4547(3) 0.5324(3) 0.15483(12) 0.0405(7) Uani 1 1 d . . . C1 C 0.3750(3) 0.4034(2) 0.32143(12) 0.0255(5) Uani 1 1 d . . . C2 C 0.4485(3) 0.3372(2) 0.28002(13) 0.0335(7) Uani 1 1 d . . . H2 H 0.4787 0.2628 0.2893 0.044 Uiso 1 1 calc R . . C3 C 0.4767(3) 0.3813(2) 0.22545(13) 0.0356(7) Uani 1 1 d . . . H3 H 0.5268 0.3366 0.1982 0.046 Uiso 1 1 calc R . . C4 C 0.4311(3) 0.4928(2) 0.21018(13) 0.0304(6) Uani 1 1 d . . . C5 C 0.3577(3) 0.5593(2) 0.25263(14) 0.0328(6) Uani 1 1 d . . . H5 H 0.3268 0.6336 0.2434 0.043 Uiso 1 1 calc R . . C6 C 0.3312(3) 0.5158(2) 0.30752(12) 0.0273(6) Uani 1 1 d . . . H6 H 0.2843 0.5610 0.3354 0.035 Uiso 1 1 calc R . . C7 C 0.5983(3) 0.3659(2) 0.44322(11) 0.0244(5) Uani 1 1 d . . . C8 C 0.8087(3) 0.4007(3) 0.49307(13) 0.0332(6) Uani 1 1 d . . . H8 H 0.8612 0.4398 0.5218 0.043 Uiso 1 1 calc R . . C9 C 0.8796(3) 0.3190(2) 0.46014(13) 0.0334(7) Uani 1 1 d . . . H9 H 0.9786 0.3029 0.4659 0.043 Uiso 1 1 calc R . . C10 C 0.7992(3) 0.2613(2) 0.41811(13) 0.0306(6) Uani 1 1 d . . . C11 C 0.8661(4) 0.1680(3) 0.38126(15) 0.0438(8) Uani 1 1 d . . . H11A H 0.8182 0.0960 0.3894 0.057 Uiso 1 1 calc R . . H11B H 0.9688 0.1615 0.3902 0.057 Uiso 1 1 calc R . . H11C H 0.8542 0.1869 0.3406 0.057 Uiso 1 1 calc R . . H1N2 H 0.417(4) 0.445(3) 0.4587(14) 0.034(9) Uiso 1 1 d . . . H1N1 H 0.514(3) 0.494(3) 0.1363(14) 0.031(9) Uiso 1 1 d . . . H2N1 H 0.448(4) 0.598(3) 0.1479(16) 0.048(11) Uiso 1 1 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 0.0268(4) 0.0263(3) 0.0231(3) -0.0018(2) 0.0000(3) -0.0029(3) O2 0.0233(11) 0.0420(10) 0.0286(10) -0.0004(9) -0.0003(8) -0.0007(8) O1 0.0443(13) 0.0258(9) 0.0319(11) -0.0020(8) -0.0008(9) -0.0069(9) N4 0.0247(14) 0.0337(11) 0.0288(12) -0.0019(10) -0.0039(10) 0.0015(9) N3 0.0337(14) 0.0281(10) 0.0281(12) -0.0022(9) 0.0031(10) 0.0030(10) N2 0.0251(14) 0.0298(11) 0.0311(13) -0.0089(10) -0.0028(10) 0.0031(9) N1 0.054(2) 0.0353(13) 0.0322(14) 0.0035(11) 0.0153(13) 0.0036(13) C1 0.0253(15) 0.0273(11) 0.0238(13) -0.0012(10) -0.0005(11) -0.0009(10) C2 0.0410(18) 0.0279(12) 0.0317(15) -0.0012(11) 0.0019(13) 0.0077(12) C3 0.0442(19) 0.0317(13) 0.0310(15) -0.0028(12) 0.0125(14) 0.0039(12) C4 0.0324(16) 0.0305(12) 0.0282(14) 0.0014(11) 0.0036(12) -0.0041(11) C5 0.0408(18) 0.0241(11) 0.0336(15) 0.0018(11) 0.0059(13) -0.0009(11) C6 0.0300(16) 0.0252(11) 0.0267(13) -0.0036(10) 0.0031(12) 0.0011(10) C7 0.0241(15) 0.0251(11) 0.0240(13) 0.0023(10) 0.0000(11) -0.0007(10) C8 0.0273(16) 0.0430(15) 0.0291(15) 0.0015(12) -0.0046(12) 0.0000(12) C9 0.0272(17) 0.0426(15) 0.0306(15) 0.0079(13) 0.0022(12) 0.0044(12) C10 0.0316(16) 0.0296(12) 0.0305(15) 0.0069(11) 0.0080(12) 0.0071(11) C11 0.038(2) 0.0435(16) 0.050(2) -0.0048(15) 0.0088(16) 0.0132(14) _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 1.4271(18) . ? S1 O2 1.440(2) . ? S1 N2 1.640(2) . ? S1 C1 1.740(3) . ? N4 C8 1.341(4) . ? N4 C7 1.343(3) . ? N3 C7 1.333(3) . ? N3 C10 1.355(4) . ? N2 C7 1.384(4) . ? N2 H1N2 0.82(3) . ? N1 C4 1.363(4) . ? N1 H1N1 0.82(3) . ? N1 H2N1 0.78(4) . ? C1 C2 1.390(4) . ? C1 C6 1.399(3) . ? C2 C3 1.372(4) . ? C2 H2 0.9300 . ? C3 C4 1.401(4) . ? C3 H3 0.9300 . ? C4 C5 1.408(4) . ? C5 C6 1.374(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.371(4) . ? C8 H8 0.9300 . ? C9 C10 1.380(4) . ? C9 H9 0.9300 . ? C10 C11 1.500(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 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 118.58(12) . . ? O1 S1 N2 109.72(12) . . ? O2 S1 N2 102.55(12) . . ? O1 S1 C1 108.60(12) . . ? O2 S1 C1 108.68(13) . . ? N2 S1 C1 108.22(13) . . ? C8 N4 C7 115.2(2) . . ? C7 N3 C10 115.2(2) . . ? C7 N2 S1 128.6(2) . . ? C7 N2 H1N2 119(2) . . ? S1 N2 H1N2 113(2) . . ? C4 N1 H1N1 114(2) . . ? C4 N1 H2N1 120(3) . . ? H1N1 N1 H2N1 119(3) . . ? C2 C1 C6 119.7(3) . . ? C2 C1 S1 120.6(2) . . ? C6 C1 S1 119.7(2) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? N1 C4 C3 119.7(3) . . ? N1 C4 C5 122.0(3) . . ? C3 C4 C5 118.3(3) . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 120.0(3) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N3 C7 N4 127.7(3) . . ? N3 C7 N2 119.3(2) . . ? N4 C7 N2 113.0(2) . . ? N4 C8 C9 122.4(3) . . ? N4 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C8 C9 C10 117.9(3) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? N3 C10 C9 121.7(3) . . ? N3 C10 C11 116.7(3) . . ? C9 C10 C11 121.7(3) . . ? 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 . . ? 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 46.5(3) . . . . ? O2 S1 N2 C7 173.4(2) . . . . ? C1 S1 N2 C7 -71.9(3) . . . . ? O1 S1 C1 C2 -17.6(3) . . . . ? O2 S1 C1 C2 -147.9(2) . . . . ? N2 S1 C1 C2 101.5(3) . . . . ? O1 S1 C1 C6 160.4(2) . . . . ? O2 S1 C1 C6 30.1(3) . . . . ? N2 S1 C1 C6 -80.5(2) . . . . ? C6 C1 C2 C3 -0.7(5) . . . . ? S1 C1 C2 C3 177.3(2) . . . . ? C1 C2 C3 C4 -0.6(5) . . . . ? C2 C3 C4 N1 -177.0(3) . . . . ? C2 C3 C4 C5 1.1(5) . . . . ? N1 C4 C5 C6 177.9(3) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C1 -1.2(4) . . . . ? C2 C1 C6 C5 1.6(4) . . . . ? S1 C1 C6 C5 -176.4(2) . . . . ? C10 N3 C7 N4 0.7(4) . . . . ? C10 N3 C7 N2 -179.2(2) . . . . ? C8 N4 C7 N3 -0.3(4) . . . . ? C8 N4 C7 N2 179.6(2) . . . . ? S1 N2 C7 N3 -2.9(4) . . . . ? S1 N2 C7 N4 177.2(2) . . . . ? C7 N4 C8 C9 0.2(4) . . . . ? N4 C8 C9 C10 -0.5(4) . . . . ? C7 N3 C10 C9 -1.0(4) . . . . ? C7 N3 C10 C11 178.1(2) . . . . ? C8 C9 C10 N3 1.0(4) . . . . ? C8 C9 C10 C11 -178.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C6 H6 O1 0.93 2.49 3.393(3) 163.3 8_665 C8 H8 O2 0.93 2.51 3.232(4) 134.4 5_666 C9 H9 O2 0.93 2.61 3.239(4) 125.8 1_655 N2 H1N2 N4 0.82(3) 2.11(3) 2.929(3) 179(3) 5_666 N1 H1N1 O2 0.82(3) 2.26(3) 3.080(4) 174(3) 6_656 N1 H2N1 O1 0.78(4) 2.53(4) 3.038(3) 124(3) 3_655 N1 H2N1 N3 0.78(4) 2.69(4) 3.418(4) 155(3) 3_655 _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 29.47 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 0.372 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.084