# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email 'srinivasulu aitipamula@ices.a-star.edu.sg' _publ_contact_author_name 'Srinivasulu Aitipamula' loop_ _publ_author_name 'Srinivasulu Aitipamula' 'Pui Shan Chow' 'Reginald B. H. Tan' data_SM-Diox(1:1) _database_code_depnum_ccdc_archive 'CCDC 840570' #TrackingRef 'SMZ-solvates-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Sulfamerazine-1,4-dioxane (1:1)' ; _chemical_name_common 'Sulfamerazine-1,4-dioxane (1:1)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N4 O4 S' _chemical_formula_weight 352.41 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 Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.511(2) _cell_length_b 12.436(3) _cell_length_c 12.095(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.05(3) _cell_angle_gamma 90.00 _cell_volume 1693.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4412 _cell_measurement_theta_min 2.3762 _cell_measurement_theta_max 31.0986 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9100 _exptl_absorpt_correction_T_max 0.9314 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13291 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4166 _reflns_number_gt 3926 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0612P)^2^+0.6995P] 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_number_reflns 4166 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.003 _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 0.73250(3) 1.02422(3) 0.82028(3) 0.02328(12) Uani 1 1 d . . . O1 O 0.71880(10) 1.02708(9) 0.69959(9) 0.0291(2) Uani 1 1 d . . . N2 N 0.87041(11) 0.99193(10) 0.87837(11) 0.0250(3) Uani 1 1 d . . . O2 O 0.71518(10) 1.12241(8) 0.87781(10) 0.0283(2) Uani 1 1 d . . . N3 N 0.87597(11) 0.83719(10) 0.77014(11) 0.0251(3) Uani 1 1 d . . . N4 N 1.03617(11) 0.88563(10) 0.92233(11) 0.0252(3) Uani 1 1 d . . . C1 C 0.64030(12) 0.92553(11) 0.85626(12) 0.0230(3) Uani 1 1 d . . . O3 O 0.31653(13) 0.59084(11) 0.11230(12) 0.0440(3) Uani 1 1 d . . . C5 C 0.50748(14) 0.77664(13) 0.80619(14) 0.0302(3) Uani 1 1 d . . . H5 H 0.4686 0.7265 0.7516 0.036 Uiso 1 1 calc R . . C6 C 0.58448(13) 0.85096(12) 0.77644(13) 0.0272(3) Uani 1 1 d . . . H6 H 0.5994 0.8514 0.7021 0.033 Uiso 1 1 calc R . . C7 C 0.92889(12) 0.89991(11) 0.85487(12) 0.0224(3) Uani 1 1 d . . . C2 C 0.61989(13) 0.92436(12) 0.96601(12) 0.0255(3) Uani 1 1 d . . . H2 H 0.6584 0.9752 1.0200 0.031 Uiso 1 1 calc R . . C10 C 1.09559(13) 0.79761(13) 0.90014(13) 0.0281(3) Uani 1 1 d . . . H10 H 1.1718 0.7833 0.9457 0.034 Uiso 1 1 calc R . . C8 C 0.93746(13) 0.75007(12) 0.74938(13) 0.0261(3) Uani 1 1 d . . . C3 C 0.54396(14) 0.84946(13) 0.99606(13) 0.0276(3) Uani 1 1 d . . . H3 H 0.5308 0.8486 1.0710 0.033 Uiso 1 1 calc R . . N1 N 0.40855(15) 0.70187(13) 0.94520(15) 0.0400(4) Uani 1 1 d . . . C9 C 1.04974(14) 0.72767(12) 0.81377(14) 0.0282(3) Uani 1 1 d . . . H9 H 1.0932 0.6664 0.7987 0.034 Uiso 1 1 calc R . . C4 C 0.48575(14) 0.77425(12) 0.91653(14) 0.0276(3) Uani 1 1 d . . . O4 O 0.14523(13) 0.43093(11) 0.11530(13) 0.0474(3) Uani 1 1 d . . . C11 C 0.87932(16) 0.68126(14) 0.65195(15) 0.0360(4) Uani 1 1 d . . . H11A H 0.7943 0.6750 0.6513 0.054 Uiso 1 1 calc R . . H11B H 0.9156 0.6096 0.6597 0.054 Uiso 1 1 calc R . . H11C H 0.8900 0.7141 0.5811 0.054 Uiso 1 1 calc R . . C12 C 0.23950(19) 0.41433(16) 0.05777(18) 0.0447(4) Uani 1 1 d . . . H12A H 0.2133 0.4353 -0.0225 0.054 Uiso 1 1 calc R . . H12B H 0.2609 0.3371 0.0605 0.054 Uiso 1 1 calc R . . C13 C 0.34599(19) 0.47949(16) 0.1112(2) 0.0501(5) Uani 1 1 d . . . H13A H 0.3760 0.4544 0.1897 0.060 Uiso 1 1 calc R . . H13B H 0.4098 0.4692 0.0685 0.060 Uiso 1 1 calc R . . C14 C 0.11732(19) 0.54238(17) 0.1181(2) 0.0508(5) Uani 1 1 d . . . H14A H 0.0540 0.5526 0.1613 0.061 Uiso 1 1 calc R . . H14B H 0.0870 0.5684 0.0400 0.061 Uiso 1 1 calc R . . C15 C 0.22424(19) 0.60677(15) 0.17165(17) 0.0424(4) Uani 1 1 d . . . H15A H 0.2032 0.6840 0.1706 0.051 Uiso 1 1 calc R . . H15B H 0.2515 0.5844 0.2514 0.051 Uiso 1 1 calc R . . H4 H 0.377(2) 0.6542(19) 0.8961(19) 0.043(6) Uiso 1 1 d . . . H7 H 0.897(2) 1.0302(18) 0.943(2) 0.047(6) Uiso 1 1 d . . . H1 H 0.3974(18) 0.6973(16) 1.0154(19) 0.036(5) 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 0.02155(19) 0.02101(19) 0.0269(2) 0.00112(12) 0.00425(14) 0.00138(12) O1 0.0312(6) 0.0292(6) 0.0269(5) 0.0049(4) 0.0058(4) 0.0014(4) N2 0.0190(6) 0.0237(6) 0.0312(6) -0.0045(5) 0.0033(5) 0.0011(5) O2 0.0260(5) 0.0211(5) 0.0371(6) -0.0012(4) 0.0049(4) 0.0031(4) N3 0.0244(6) 0.0246(6) 0.0268(6) -0.0023(5) 0.0062(5) 0.0000(5) N4 0.0218(6) 0.0254(6) 0.0282(6) -0.0013(5) 0.0050(5) 0.0014(5) C1 0.0199(6) 0.0223(6) 0.0266(7) 0.0009(5) 0.0046(5) 0.0014(5) O3 0.0499(8) 0.0372(7) 0.0522(8) -0.0082(6) 0.0275(6) -0.0134(6) C5 0.0295(8) 0.0306(8) 0.0302(8) -0.0063(6) 0.0057(6) -0.0063(6) C6 0.0269(7) 0.0295(7) 0.0249(7) -0.0033(6) 0.0050(6) -0.0019(6) C7 0.0209(6) 0.0217(6) 0.0257(6) 0.0002(5) 0.0076(5) 0.0000(5) C2 0.0260(7) 0.0254(7) 0.0249(7) -0.0033(5) 0.0048(5) -0.0014(6) C10 0.0235(7) 0.0295(7) 0.0313(7) -0.0005(6) 0.0061(6) 0.0030(6) C8 0.0291(7) 0.0240(7) 0.0267(7) -0.0005(5) 0.0096(6) 0.0003(6) C3 0.0294(7) 0.0290(7) 0.0259(7) -0.0030(6) 0.0090(6) -0.0007(6) N1 0.0453(9) 0.0389(8) 0.0405(8) -0.0094(7) 0.0195(7) -0.0177(7) C9 0.0275(7) 0.0253(7) 0.0329(8) -0.0024(6) 0.0087(6) 0.0034(6) C4 0.0252(7) 0.0265(7) 0.0325(8) -0.0021(6) 0.0090(6) -0.0015(6) O4 0.0487(8) 0.0380(7) 0.0579(9) 0.0053(6) 0.0167(7) -0.0123(6) C11 0.0388(9) 0.0342(8) 0.0336(8) -0.0096(7) 0.0043(7) 0.0045(7) C12 0.0553(12) 0.0354(9) 0.0453(10) -0.0054(8) 0.0145(9) -0.0080(8) C13 0.0426(11) 0.0417(11) 0.0701(14) -0.0133(9) 0.0209(10) -0.0044(8) C14 0.0416(11) 0.0456(11) 0.0682(14) 0.0061(10) 0.0181(10) -0.0008(9) C15 0.0534(11) 0.0352(9) 0.0447(10) -0.0022(7) 0.0245(9) -0.0037(8) _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 1.4356(12) . ? S1 O2 1.4397(11) . ? S1 N2 1.6461(14) . ? S1 C1 1.7364(15) . ? N2 C7 1.3869(18) . ? N2 H7 0.92(2) . ? N3 C7 1.3302(19) . ? N3 C8 1.3462(19) . ? N4 C7 1.3423(19) . ? N4 C10 1.3471(19) . ? C1 C6 1.395(2) . ? C1 C2 1.396(2) . ? O3 C15 1.415(2) . ? O3 C13 1.426(2) . ? C5 C6 1.379(2) . ? C5 C4 1.409(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C2 C3 1.377(2) . ? C2 H2 0.9500 . ? C10 C9 1.377(2) . ? C10 H10 0.9500 . ? C8 C9 1.391(2) . ? C8 C11 1.497(2) . ? C3 C4 1.407(2) . ? C3 H3 0.9500 . ? N1 C4 1.360(2) . ? N1 H4 0.86(2) . ? N1 H1 0.89(2) . ? C9 H9 0.9500 . ? O4 C12 1.421(3) . ? O4 C14 1.425(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.499(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.498(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? 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 118.26(7) . . ? O1 S1 N2 109.36(7) . . ? O2 S1 N2 102.66(7) . . ? O1 S1 C1 109.22(7) . . ? O2 S1 C1 108.96(7) . . ? N2 S1 C1 107.82(7) . . ? C7 N2 S1 125.45(11) . . ? C7 N2 H7 121.2(15) . . ? S1 N2 H7 110.9(15) . . ? C7 N3 C8 116.20(13) . . ? C7 N4 C10 115.30(13) . . ? C6 C1 C2 120.44(13) . . ? C6 C1 S1 120.92(11) . . ? C2 C1 S1 118.60(11) . . ? C15 O3 C13 110.22(15) . . ? C6 C5 C4 120.81(14) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 119.55(14) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? N3 C7 N4 127.31(13) . . ? N3 C7 N2 118.55(13) . . ? N4 C7 N2 114.14(13) . . ? C3 C2 C1 120.02(14) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? N4 C10 C9 122.29(14) . . ? N4 C10 H10 118.9 . . ? C9 C10 H10 118.9 . . ? N3 C8 C9 121.34(14) . . ? N3 C8 C11 116.16(14) . . ? C9 C8 C11 122.48(14) . . ? C2 C3 C4 120.47(14) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C4 N1 H4 118.9(15) . . ? C4 N1 H1 121.3(14) . . ? H4 N1 H1 119(2) . . ? C10 C9 C8 117.55(14) . . ? C10 C9 H9 121.2 . . ? C8 C9 H9 121.2 . . ? N1 C4 C3 120.60(15) . . ? N1 C4 C5 120.69(15) . . ? C3 C4 C5 118.70(14) . . ? C12 O4 C14 110.60(15) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O4 C12 C13 110.46(16) . . ? O4 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? O4 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O3 C13 C12 110.74(18) . . ? O3 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? O4 C14 C15 111.18(17) . . ? O4 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? O4 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? O3 C15 C14 109.99(16) . . ? O3 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? O3 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.286 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.051 #====END data_SM-Diox(1:0.5) _database_code_depnum_ccdc_archive 'CCDC 840571' #TrackingRef 'SMZ-solvates-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Sulfamerazine-1,4-dioxane (1:0.5)' ; _chemical_name_common 'Sulfamerazine-1,4-dioxane (1:0.5)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 N4 O3 S' _chemical_formula_weight 308.36 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7675(16) _cell_length_b 8.1233(16) _cell_length_c 12.631(3) _cell_angle_alpha 91.16(3) _cell_angle_beta 95.69(3) _cell_angle_gamma 105.23(3) _cell_volume 764.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2572 _cell_measurement_theta_min 1.6221 _cell_measurement_theta_max 30.9634 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9518 _exptl_absorpt_correction_T_max 0.9518 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10768 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3750 _reflns_number_gt 3591 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0502P)^2^+0.3873P] 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_number_reflns 3750 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.001 _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 0.12079(5) 0.51419(5) 0.76835(3) 0.02287(11) Uani 1 1 d . . . O3 O 0.12072(15) 0.99926(15) 0.09194(9) 0.0273(2) Uani 1 1 d . . . O2 O -0.06584(15) 0.44087(15) 0.78071(9) 0.0280(3) Uani 1 1 d . . . O1 O 0.21727(16) 0.66478(14) 0.83125(9) 0.0282(3) Uani 1 1 d . . . N2 N 0.11404(18) 0.55840(17) 0.64128(10) 0.0242(3) Uani 1 1 d . . . N3 N 0.42399(17) 0.67181(17) 0.64132(10) 0.0244(3) Uani 1 1 d . . . C1 C 0.23722(19) 0.35944(19) 0.78499(11) 0.0213(3) Uani 1 1 d . . . C5 C 0.5052(2) 0.2777(2) 0.84469(13) 0.0254(3) Uani 1 1 d . . . H5 H 0.6248 0.3066 0.8784 0.030 Uiso 1 1 calc R . . N4 N 0.22325(18) 0.61693(18) 0.48017(11) 0.0282(3) Uani 1 1 d . . . C2 C 0.1524(2) 0.19197(19) 0.74789(12) 0.0231(3) Uani 1 1 d . . . H2 H 0.0320 0.1635 0.7155 0.028 Uiso 1 1 calc R . . C3 C 0.2440(2) 0.06783(19) 0.75852(12) 0.0239(3) Uani 1 1 d . . . H3 H 0.1862 -0.0461 0.7331 0.029 Uiso 1 1 calc R . . N1 N 0.5127(2) -0.01411(19) 0.81513(14) 0.0353(3) Uani 1 1 d . . . C6 C 0.4139(2) 0.4027(2) 0.83337(12) 0.0239(3) Uani 1 1 d . . . H6 H 0.4710 0.5170 0.8583 0.029 Uiso 1 1 calc R . . C7 C 0.2625(2) 0.61874(19) 0.58629(12) 0.0232(3) Uani 1 1 d . . . C4 C 0.4228(2) 0.1086(2) 0.80686(12) 0.0245(3) Uani 1 1 d . . . C8 C 0.5635(2) 0.7306(2) 0.58471(13) 0.0278(3) Uani 1 1 d . . . C13 C 0.0730(2) 0.8616(2) 0.01264(13) 0.0288(3) Uani 1 1 d . . . H13A H 0.0760 0.7535 0.0467 0.035 Uiso 1 1 calc R . . H13B H 0.1616 0.8825 -0.0401 0.035 Uiso 1 1 calc R . . C9 C 0.5378(2) 0.7381(2) 0.47461(14) 0.0346(4) Uani 1 1 d . . . H9 H 0.6355 0.7822 0.4345 0.042 Uiso 1 1 calc R . . C12 C 0.1117(2) 1.1551(2) 0.04331(13) 0.0297(3) Uani 1 1 d . . . H12A H 0.2013 1.1832 -0.0086 0.036 Uiso 1 1 calc R . . H12B H 0.1410 1.2493 0.0985 0.036 Uiso 1 1 calc R . . C10 C 0.3639(2) 0.6786(2) 0.42585(14) 0.0345(4) Uani 1 1 d . . . H10 H 0.3436 0.6817 0.3506 0.041 Uiso 1 1 calc R . . C11 C 0.7458(2) 0.7857(3) 0.64641(15) 0.0363(4) Uani 1 1 d . . . H11A H 0.7528 0.8851 0.6935 0.055 Uiso 1 1 calc R . . H11B H 0.8374 0.8162 0.5969 0.055 Uiso 1 1 calc R . . H11C H 0.7664 0.6920 0.6891 0.055 Uiso 1 1 calc R . . H1 H 0.450(3) -0.124(3) 0.7986(18) 0.042(6) Uiso 1 1 d . . . H4 H 0.624(3) 0.009(3) 0.850(2) 0.052(7) Uiso 1 1 d . . . H7 H 0.015(3) 0.505(3) 0.6024(18) 0.039(6) 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 0.02354(19) 0.0259(2) 0.02156(19) 0.00444(14) 0.00578(13) 0.00925(14) O3 0.0278(6) 0.0338(6) 0.0217(5) 0.0031(4) 0.0010(4) 0.0111(5) O2 0.0238(5) 0.0364(6) 0.0272(6) 0.0094(5) 0.0087(4) 0.0112(5) O1 0.0340(6) 0.0270(6) 0.0257(6) 0.0002(4) 0.0059(5) 0.0108(5) N2 0.0211(6) 0.0311(7) 0.0212(6) 0.0061(5) 0.0040(5) 0.0075(5) N3 0.0228(6) 0.0260(6) 0.0251(6) 0.0018(5) 0.0049(5) 0.0068(5) C1 0.0224(7) 0.0231(7) 0.0198(6) 0.0037(5) 0.0037(5) 0.0077(5) C5 0.0192(7) 0.0270(7) 0.0287(8) 0.0014(6) 0.0021(6) 0.0041(6) N4 0.0253(6) 0.0355(7) 0.0234(6) 0.0059(5) 0.0059(5) 0.0059(5) C2 0.0206(7) 0.0258(7) 0.0225(7) 0.0029(6) 0.0035(5) 0.0047(5) C3 0.0231(7) 0.0217(7) 0.0254(7) 0.0008(6) 0.0028(5) 0.0034(5) N1 0.0255(7) 0.0260(7) 0.0543(10) -0.0061(7) -0.0047(6) 0.0106(6) C6 0.0217(7) 0.0233(7) 0.0255(7) 0.0020(6) 0.0036(5) 0.0034(5) C7 0.0236(7) 0.0233(7) 0.0244(7) 0.0034(6) 0.0052(5) 0.0081(6) C4 0.0240(7) 0.0254(7) 0.0257(7) 0.0018(6) 0.0042(6) 0.0090(6) C8 0.0253(7) 0.0289(8) 0.0291(8) 0.0000(6) 0.0058(6) 0.0059(6) C13 0.0321(8) 0.0339(8) 0.0238(7) 0.0028(6) 0.0034(6) 0.0146(7) C9 0.0257(8) 0.0450(10) 0.0302(8) 0.0043(7) 0.0104(6) 0.0012(7) C12 0.0325(8) 0.0312(8) 0.0252(7) 0.0030(6) 0.0026(6) 0.0084(6) C10 0.0303(8) 0.0470(10) 0.0243(8) 0.0057(7) 0.0086(6) 0.0044(7) C11 0.0234(8) 0.0470(10) 0.0357(9) -0.0034(8) 0.0043(7) 0.0044(7) _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 1.4319(13) . ? S1 O2 1.4408(12) . ? S1 N2 1.6505(13) . ? S1 C1 1.7356(15) . ? O3 C12 1.433(2) . ? O3 C13 1.434(2) . ? N2 C7 1.3887(19) . ? N2 H7 0.87(2) . ? N3 C7 1.332(2) . ? N3 C8 1.345(2) . ? C1 C2 1.395(2) . ? C1 C6 1.397(2) . ? C5 C6 1.385(2) . ? C5 C4 1.406(2) . ? C5 H5 0.9500 . ? N4 C10 1.338(2) . ? N4 C7 1.344(2) . ? C2 C3 1.380(2) . ? C2 H2 0.9500 . ? C3 C4 1.412(2) . ? C3 H3 0.9500 . ? N1 C4 1.360(2) . ? N1 H1 0.91(2) . ? N1 H4 0.91(3) . ? C6 H6 0.9500 . ? C8 C9 1.390(2) . ? C8 C11 1.499(2) . ? C13 C12 1.507(2) 2_575 ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C9 C10 1.385(2) . ? C9 H9 0.9500 . ? C12 C13 1.507(2) 2_575 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 118.98(8) . . ? O1 S1 N2 109.05(8) . . ? O2 S1 N2 102.39(7) . . ? O1 S1 C1 108.98(7) . . ? O2 S1 C1 109.72(7) . . ? N2 S1 C1 106.97(7) . . ? C12 O3 C13 109.62(12) . . ? C7 N2 S1 125.44(11) . . ? C7 N2 H7 115.7(15) . . ? S1 N2 H7 114.9(15) . . ? C7 N3 C8 116.59(14) . . ? C2 C1 C6 120.66(14) . . ? C2 C1 S1 118.91(11) . . ? C6 C1 S1 120.43(12) . . ? C6 C5 C4 120.73(14) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C10 N4 C7 115.04(14) . . ? C3 C2 C1 119.74(14) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.61(14) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C4 N1 H1 118.1(14) . . ? C4 N1 H4 120.7(16) . . ? H1 N1 H4 120(2) . . ? C5 C6 C1 119.52(14) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? N3 C7 N4 127.19(14) . . ? N3 C7 N2 118.74(14) . . ? N4 C7 N2 114.07(14) . . ? N1 C4 C5 121.20(14) . . ? N1 C4 C3 120.06(15) . . ? C5 C4 C3 118.74(14) . . ? N3 C8 C9 121.06(15) . . ? N3 C8 C11 116.56(15) . . ? C9 C8 C11 122.38(15) . . ? O3 C13 C12 110.84(13) . 2_575 ? O3 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 2_575 . ? O3 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 2_575 . ? H13A C13 H13B 108.1 . . ? C10 C9 C8 117.26(15) . . ? C10 C9 H9 121.4 . . ? C8 C9 H9 121.4 . . ? O3 C12 C13 110.68(14) . 2_575 ? O3 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 2_575 . ? O3 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 2_575 . ? H12A C12 H12B 108.1 . . ? N4 C10 C9 122.84(16) . . ? N4 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.271 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.054 #====END data_SM-DMF _database_code_depnum_ccdc_archive 'CCDC 840572' #TrackingRef 'SMZ-solvates-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Sulfamerazine-dimethylformamide(1:1)' ; _chemical_name_common Sulfamerazine-dimethylformamide(1:1) _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N4 O2 S, C3 H7 N O' _chemical_formula_sum 'C14 H19 N5 O3 S' _chemical_formula_weight 337.41 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.774(2) _cell_length_b 12.556(3) _cell_length_c 14.659(3) _cell_angle_alpha 76.58(3) _cell_angle_beta 77.57(3) _cell_angle_gamma 86.18(3) _cell_volume 1708.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4034 _cell_measurement_theta_min 2.3243 _cell_measurement_theta_max 31.0936 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9130 _exptl_absorpt_correction_T_max 0.9551 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24377 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.28 _reflns_number_total 8380 _reflns_number_gt 7310 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0686P)^2^+1.1323P] 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_number_reflns 8380 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.1783 _refine_ls_wR_factor_gt 0.1708 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _refine_ls_shift/su_max 0.001 _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 0.64137(5) 0.72662(4) 0.24282(3) 0.02293(14) Uani 1 1 d . . . S2A S 0.14275(5) 0.22452(4) 0.24239(3) 0.02372(14) Uani 1 1 d . . . N5 N 0.6808(2) 0.38749(16) 0.45624(14) 0.0371(5) Uani 1 1 d . . . O3 O 0.5453(2) 0.33631(16) 0.36630(14) 0.0452(5) Uani 1 1 d . . . N5A N 0.1672(3) 0.12088(19) 0.52900(15) 0.0446(5) Uani 1 1 d . . . C12 C 0.5929(3) 0.4064(2) 0.39591(18) 0.0401(6) Uani 1 1 d . . . H12 H 0.5650 0.4802 0.3741 0.048 Uiso 1 1 calc R . . O1A O 0.01124(16) 0.18147(12) 0.29868(11) 0.0283(3) Uani 1 1 d . . . O2A O 0.26824(16) 0.16160(12) 0.25404(11) 0.0290(3) Uani 1 1 d . . . O2 O 0.76648(16) 0.66324(12) 0.25527(10) 0.0276(3) Uani 1 1 d . . . O1 O 0.50981(16) 0.68487(12) 0.30019(10) 0.0269(3) Uani 1 1 d . . . C14 C 0.7252(3) 0.2765(2) 0.49435(18) 0.0451(6) Uani 1 1 d . . . H14A H 0.6753 0.2247 0.4730 0.068 Uiso 1 1 calc R . . H14B H 0.7042 0.2616 0.5645 0.068 Uiso 1 1 calc R . . H14C H 0.8263 0.2682 0.4712 0.068 Uiso 1 1 calc R . . N2A N 0.14298(19) 0.23487(14) 0.12787(12) 0.0246(4) Uani 1 1 d . . . N3A N -0.06631(18) 0.33624(14) 0.12555(12) 0.0247(4) Uani 1 1 d . . . N3 N 0.43091(18) 0.83646(14) 0.12798(12) 0.0241(4) Uani 1 1 d . . . N2 N 0.6409(2) 0.73546(14) 0.12885(13) 0.0247(4) Uani 1 1 d . . . N1A N 0.2057(2) 0.67601(17) 0.27551(16) 0.0330(4) Uani 1 1 d . . . C2A C 0.2939(2) 0.40188(18) 0.23061(15) 0.0262(4) Uani 1 1 d . . . H2A H 0.3734 0.3603 0.2078 0.031 Uiso 1 1 calc R . . C13A C 0.2193(4) 0.0183(3) 0.5027(2) 0.0546(8) Uani 1 1 d . . . H13A H 0.1545 -0.0405 0.5384 0.082 Uiso 1 1 calc R . . H13B H 0.3120 0.0006 0.5183 0.082 Uiso 1 1 calc R . . H13C H 0.2265 0.0259 0.4338 0.082 Uiso 1 1 calc R . . N4A N 0.08613(19) 0.30693(15) -0.01807(13) 0.0284(4) Uani 1 1 d . . . C6 C 0.5453(2) 0.91809(17) 0.29307(14) 0.0240(4) Uani 1 1 d . . . H6 H 0.4553 0.8862 0.3129 0.029 Uiso 1 1 calc R . . N4 N 0.5830(2) 0.80929(16) -0.01679(13) 0.0295(4) Uani 1 1 d . . . C5A C 0.0595(2) 0.52148(17) 0.29988(14) 0.0253(4) Uani 1 1 d . . . H5A H -0.0198 0.5618 0.3248 0.030 Uiso 1 1 calc R . . C1 C 0.6611(2) 0.85855(16) 0.25538(14) 0.0225(4) Uani 1 1 d . . . C1A C 0.1605(2) 0.35591(16) 0.25697(14) 0.0229(4) Uani 1 1 d . . . C5 C 0.5626(2) 1.02379(17) 0.30127(14) 0.0246(4) Uani 1 1 d . . . H5 H 0.4843 1.0637 0.3283 0.029 Uiso 1 1 calc R . . C13 C 0.7275(3) 0.4759(2) 0.4911(2) 0.0492(7) Uani 1 1 d . . . H13D H 0.6960 0.5464 0.4564 0.074 Uiso 1 1 calc R . . H13E H 0.8300 0.4739 0.4805 0.074 Uiso 1 1 calc R . . H13F H 0.6878 0.4666 0.5597 0.074 Uiso 1 1 calc R . . C2 C 0.7929(2) 0.90575(18) 0.22458(15) 0.0264(4) Uani 1 1 d . . . H2 H 0.8710 0.8650 0.1988 0.032 Uiso 1 1 calc R . . C7 C 0.5458(2) 0.79721(16) 0.07871(14) 0.0229(4) Uani 1 1 d . . . C12A C 0.0453(4) 0.1207(4) 0.5899(2) 0.0670(10) Uani 1 1 d . . . H12A H -0.0039 0.0538 0.6121 0.080 Uiso 1 1 calc R . . C3A C 0.3094(2) 0.50786(18) 0.23795(16) 0.0288(4) Uani 1 1 d . . . H3A H 0.3999 0.5390 0.2201 0.035 Uiso 1 1 calc R . . C3 C 0.8102(2) 1.01163(18) 0.23146(15) 0.0271(4) Uani 1 1 d . . . H3 H 0.9002 1.0435 0.2101 0.032 Uiso 1 1 calc R . . C7A C 0.0486(2) 0.29593(16) 0.07733(14) 0.0230(4) Uani 1 1 d . . . O3A O -0.0077(4) 0.1991(3) 0.6192(2) 0.1167(15) Uani 1 1 d . . . C8 C 0.3409(2) 0.89374(17) 0.07673(16) 0.0278(4) Uani 1 1 d . . . C4 C 0.6949(2) 1.07274(17) 0.27002(15) 0.0252(4) Uani 1 1 d . . . N1 N 0.7111(2) 1.17757(17) 0.27502(16) 0.0344(4) Uani 1 1 d . . . C6A C 0.0435(2) 0.41559(17) 0.29172(14) 0.0241(4) Uani 1 1 d . . . H6A H -0.0467 0.3838 0.3097 0.029 Uiso 1 1 calc R . . C4A C 0.1926(2) 0.57033(17) 0.27156(15) 0.0254(4) Uani 1 1 d . . . C8A C -0.1556(2) 0.39376(18) 0.07336(16) 0.0280(4) Uani 1 1 d . . . C11A C -0.2833(3) 0.4413(2) 0.12734(18) 0.0367(5) Uani 1 1 d . . . H11A H -0.3432 0.3820 0.1686 0.055 Uiso 1 1 calc R . . H11B H -0.3350 0.4873 0.0819 0.055 Uiso 1 1 calc R . . H11C H -0.2553 0.4858 0.1668 0.055 Uiso 1 1 calc R . . C14A C 0.2573(5) 0.2126(3) 0.4924(3) 0.0912(15) Uani 1 1 d . . . H14D H 0.2097 0.2772 0.5123 0.137 Uiso 1 1 calc R . . H14E H 0.2807 0.2267 0.4223 0.137 Uiso 1 1 calc R . . H14F H 0.3434 0.1970 0.5176 0.137 Uiso 1 1 calc R . . C9A C -0.1286(3) 0.4075(2) -0.02559(16) 0.0350(5) Uani 1 1 d . . . H9A H -0.1921 0.4465 -0.0627 0.042 Uiso 1 1 calc R . . C10 C 0.4910(3) 0.8652(2) -0.06601(17) 0.0375(5) Uani 1 1 d . . . H10 H 0.5113 0.8753 -0.1338 0.045 Uiso 1 1 calc R . . C9 C 0.3674(3) 0.9090(2) -0.02234(17) 0.0357(5) Uani 1 1 d . . . H9 H 0.3031 0.9481 -0.0588 0.043 Uiso 1 1 calc R . . C11 C 0.2126(2) 0.9399(2) 0.13160(18) 0.0359(5) Uani 1 1 d . . . H11D H 0.1526 0.8799 0.1716 0.054 Uiso 1 1 calc R . . H11E H 0.1612 0.9871 0.0867 0.054 Uiso 1 1 calc R . . H11F H 0.2401 0.9828 0.1725 0.054 Uiso 1 1 calc R . . C10A C -0.0055(3) 0.3622(2) -0.06784(16) 0.0354(5) Uani 1 1 d . . . H10A H 0.0149 0.3708 -0.1355 0.043 Uiso 1 1 calc R . . H7A H 0.223(3) 0.223(2) 0.094(2) 0.034(7) Uiso 1 1 d . . . H1 H 0.797(4) 1.201(3) 0.261(2) 0.053(9) Uiso 1 1 d . . . H4A H 0.137(4) 0.709(3) 0.307(2) 0.050(9) Uiso 1 1 d . . . H4 H 0.647(3) 1.208(3) 0.306(2) 0.046(9) Uiso 1 1 d . . . H1A H 0.286(3) 0.695(2) 0.264(2) 0.044(8) Uiso 1 1 d . . . H7 H 0.724(3) 0.722(2) 0.094(2) 0.042(8) 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 0.0248(3) 0.0230(3) 0.0209(2) -0.00296(19) -0.00702(19) 0.00177(19) S2A 0.0264(3) 0.0244(3) 0.0207(2) -0.00342(19) -0.0080(2) 0.00181(19) N5 0.0451(12) 0.0352(11) 0.0269(9) -0.0027(8) -0.0047(9) 0.0037(9) O3 0.0474(11) 0.0451(10) 0.0465(11) -0.0156(9) -0.0150(9) 0.0116(8) N5A 0.0522(14) 0.0510(13) 0.0310(10) -0.0067(10) -0.0148(10) 0.0082(11) C12 0.0465(15) 0.0363(13) 0.0337(12) -0.0064(10) -0.0048(11) 0.0083(11) O1A 0.0310(8) 0.0273(7) 0.0247(7) -0.0009(6) -0.0055(6) -0.0041(6) O2A 0.0319(8) 0.0306(8) 0.0261(7) -0.0059(6) -0.0127(6) 0.0084(6) O2 0.0295(8) 0.0287(8) 0.0252(7) -0.0050(6) -0.0109(6) 0.0095(6) O1 0.0288(8) 0.0242(7) 0.0258(7) -0.0013(6) -0.0056(6) -0.0027(6) C14 0.0538(17) 0.0458(15) 0.0328(13) -0.0047(11) -0.0106(12) 0.0117(12) N2A 0.0249(9) 0.0284(9) 0.0204(8) -0.0062(7) -0.0061(7) 0.0073(7) N3A 0.0254(9) 0.0245(8) 0.0228(8) -0.0022(7) -0.0058(7) 0.0007(7) N3 0.0229(9) 0.0239(8) 0.0252(8) -0.0039(7) -0.0068(7) 0.0015(7) N2 0.0264(9) 0.0271(9) 0.0218(8) -0.0063(7) -0.0082(7) 0.0052(7) N1A 0.0296(11) 0.0297(10) 0.0386(11) -0.0091(8) -0.0028(9) -0.0018(8) C2A 0.0212(10) 0.0319(11) 0.0267(10) -0.0095(8) -0.0050(8) 0.0019(8) C13A 0.0619(19) 0.0617(19) 0.0386(15) -0.0070(13) -0.0135(14) 0.0057(15) N4A 0.0274(9) 0.0351(10) 0.0231(9) -0.0067(7) -0.0081(7) 0.0065(8) C6 0.0195(9) 0.0293(10) 0.0210(9) -0.0016(8) -0.0035(7) -0.0009(8) N4 0.0291(10) 0.0358(10) 0.0239(9) -0.0062(8) -0.0090(7) 0.0067(8) C5A 0.0218(10) 0.0310(11) 0.0219(9) -0.0045(8) -0.0041(8) 0.0020(8) C1 0.0210(10) 0.0255(10) 0.0211(9) -0.0037(8) -0.0066(8) 0.0003(7) C1A 0.0250(10) 0.0255(10) 0.0198(9) -0.0064(8) -0.0069(8) 0.0013(8) C5 0.0233(10) 0.0260(10) 0.0236(9) -0.0044(8) -0.0053(8) 0.0032(8) C13 0.0593(18) 0.0520(16) 0.0339(13) -0.0064(12) -0.0040(12) -0.0131(14) C2 0.0224(10) 0.0313(11) 0.0260(10) -0.0073(8) -0.0062(8) 0.0032(8) C7 0.0260(10) 0.0213(9) 0.0221(9) -0.0025(7) -0.0090(8) 0.0003(8) C12A 0.056(2) 0.105(3) 0.0447(17) -0.0243(18) -0.0222(15) 0.0303(19) C3A 0.0216(10) 0.0345(11) 0.0309(11) -0.0077(9) -0.0064(8) -0.0016(8) C3 0.0207(10) 0.0329(11) 0.0282(10) -0.0074(9) -0.0047(8) -0.0037(8) C7A 0.0244(10) 0.0220(9) 0.0225(9) -0.0029(8) -0.0066(8) -0.0007(8) O3A 0.130(3) 0.166(3) 0.0800(19) -0.078(2) -0.0588(19) 0.117(3) C8 0.0284(11) 0.0247(10) 0.0291(10) -0.0015(8) -0.0086(9) 0.0017(8) C4 0.0265(10) 0.0248(10) 0.0240(9) -0.0024(8) -0.0078(8) -0.0018(8) N1 0.0316(11) 0.0288(10) 0.0422(12) -0.0102(9) -0.0027(9) -0.0049(8) C6A 0.0228(10) 0.0283(10) 0.0220(9) -0.0049(8) -0.0067(8) -0.0008(8) C4A 0.0273(10) 0.0278(10) 0.0219(9) -0.0044(8) -0.0081(8) -0.0003(8) C8A 0.0244(10) 0.0301(11) 0.0277(10) -0.0021(9) -0.0059(8) -0.0005(8) C11A 0.0294(12) 0.0395(13) 0.0353(12) -0.0029(10) -0.0024(10) 0.0080(10) C14A 0.162(5) 0.065(2) 0.058(2) 0.0058(17) -0.056(3) -0.045(2) C9A 0.0317(12) 0.0437(13) 0.0265(11) -0.0013(10) -0.0096(9) 0.0096(10) C10 0.0382(13) 0.0483(14) 0.0250(11) -0.0034(10) -0.0126(10) 0.0100(11) C9 0.0292(12) 0.0447(14) 0.0313(11) -0.0013(10) -0.0131(10) 0.0091(10) C11 0.0273(11) 0.0362(12) 0.0393(13) -0.0027(10) -0.0056(10) 0.0084(9) C10A 0.0343(12) 0.0483(14) 0.0224(10) -0.0034(10) -0.0104(9) 0.0076(10) _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 1.4335(16) . ? S1 O2 1.4357(15) . ? S1 N2 1.6493(18) . ? S1 C1 1.736(2) . ? S2A O1A 1.4332(16) . ? S2A O2A 1.4339(16) . ? S2A N2A 1.6529(18) . ? S2A C1A 1.736(2) . ? N5 C12 1.334(3) . ? N5 C14 1.451(3) . ? N5 C13 1.460(3) . ? O3 C12 1.224(3) . ? N5A C12A 1.326(4) . ? N5A C14A 1.427(4) . ? N5A C13A 1.458(4) . ? C12 H12 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N2A C7A 1.387(3) . ? N2A H7A 0.86(3) . ? N3A C7A 1.329(3) . ? N3A C8A 1.348(3) . ? N3 C7 1.330(3) . ? N3 C8 1.344(3) . ? N2 C7 1.393(3) . ? N2 H7 0.89(3) . ? N1A C4A 1.357(3) . ? N1A H4A 0.87(3) . ? N1A H1A 0.81(3) . ? C2A C3A 1.380(3) . ? C2A C1A 1.401(3) . ? C2A H2A 0.9500 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? N4A C10A 1.334(3) . ? N4A C7A 1.344(3) . ? C6 C5 1.384(3) . ? C6 C1 1.398(3) . ? C6 H6 0.9500 . ? N4 C10 1.335(3) . ? N4 C7 1.343(3) . ? C5A C6A 1.384(3) . ? C5A C4A 1.412(3) . ? C5A H5A 0.9500 . ? C1 C2 1.393(3) . ? C1A C6A 1.393(3) . ? C5 C4 1.408(3) . ? C5 H5 0.9500 . ? C13 H13D 0.9800 . ? C13 H13E 0.9800 . ? C13 H13F 0.9800 . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? C12A O3A 1.207(4) . ? C12A H12A 0.9500 . ? C3A C4A 1.407(3) . ? C3A H3A 0.9500 . ? C3 C4 1.410(3) . ? C3 H3 0.9500 . ? C8 C9 1.389(3) . ? C8 C11 1.496(3) . ? C4 N1 1.357(3) . ? N1 H1 0.88(3) . ? N1 H4 0.82(3) . ? C6A H6A 0.9500 . ? C8A C9A 1.389(3) . ? C8A C11A 1.495(3) . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? C14A H14D 0.9800 . ? C14A H14E 0.9800 . ? C14A H14F 0.9800 . ? C9A C10A 1.380(3) . ? C9A H9A 0.9500 . ? C10 C9 1.384(3) . ? C10 H10 0.9500 . ? C9 H9 0.9500 . ? C11 H11D 0.9800 . ? C11 H11E 0.9800 . ? C11 H11F 0.9800 . ? C10A H10A 0.9500 . ? 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 118.53(9) . . ? O1 S1 N2 109.27(10) . . ? O2 S1 N2 102.58(10) . . ? O1 S1 C1 109.36(10) . . ? O2 S1 C1 109.52(10) . . ? N2 S1 C1 106.86(10) . . ? O1A S2A O2A 118.71(10) . . ? O1A S2A N2A 108.95(10) . . ? O2A S2A N2A 102.33(9) . . ? O1A S2A C1A 109.36(10) . . ? O2A S2A C1A 109.71(10) . . ? N2A S2A C1A 107.04(10) . . ? C12 N5 C14 120.4(2) . . ? C12 N5 C13 121.5(2) . . ? C14 N5 C13 117.9(2) . . ? C12A N5A C14A 124.7(3) . . ? C12A N5A C13A 118.3(3) . . ? C14A N5A C13A 116.9(3) . . ? O3 C12 N5 125.3(2) . . ? O3 C12 H12 117.3 . . ? N5 C12 H12 117.3 . . ? N5 C14 H14A 109.5 . . ? N5 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N5 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7A N2A S2A 125.93(15) . . ? C7A N2A H7A 115.0(19) . . ? S2A N2A H7A 114.5(18) . . ? C7A N3A C8A 116.63(18) . . ? C7 N3 C8 116.49(18) . . ? C7 N2 S1 125.27(15) . . ? C7 N2 H7 116.3(19) . . ? S1 N2 H7 114.0(19) . . ? C4A N1A H4A 120(2) . . ? C4A N1A H1A 114(2) . . ? H4A N1A H1A 123(3) . . ? C3A C2A C1A 119.67(19) . . ? C3A C2A H2A 120.2 . . ? C1A C2A H2A 120.2 . . ? N5A C13A H13A 109.5 . . ? N5A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? N5A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C10A N4A C7A 115.08(19) . . ? C5 C6 C1 119.68(19) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C10 N4 C7 115.04(19) . . ? C6A C5A C4A 120.75(19) . . ? C6A C5A H5A 119.6 . . ? C4A C5A H5A 119.6 . . ? C2 C1 C6 120.33(19) . . ? C2 C1 S1 119.20(16) . . ? C6 C1 S1 120.44(16) . . ? C6A C1A C2A 120.67(19) . . ? C6A C1A S2A 120.51(16) . . ? C2A C1A S2A 118.79(16) . . ? C6 C5 C4 120.63(19) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? N5 C13 H13D 109.5 . . ? N5 C13 H13E 109.5 . . ? H13D C13 H13E 109.5 . . ? N5 C13 H13F 109.5 . . ? H13D C13 H13F 109.5 . . ? H13E C13 H13F 109.5 . . ? C3 C2 C1 120.19(19) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? N3 C7 N4 127.34(19) . . ? N3 C7 N2 118.58(18) . . ? N4 C7 N2 114.08(18) . . ? O3A C12A N5A 124.9(4) . . ? O3A C12A H12A 117.6 . . ? N5A C12A H12A 117.6 . . ? C2A C3A C4A 120.7(2) . . ? C2A C3A H3A 119.6 . . ? C4A C3A H3A 119.6 . . ? C2 C3 C4 120.35(19) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? N3A C7A N4A 127.05(19) . . ? N3A C7A N2A 118.86(18) . . ? N4A C7A N2A 114.09(18) . . ? N3 C8 C9 120.9(2) . . ? N3 C8 C11 116.8(2) . . ? C9 C8 C11 122.3(2) . . ? N1 C4 C5 120.7(2) . . ? N1 C4 C3 120.5(2) . . ? C5 C4 C3 118.82(19) . . ? C4 N1 H1 116(2) . . ? C4 N1 H4 119(2) . . ? H1 N1 H4 122(3) . . ? C5A C6A C1A 119.51(19) . . ? C5A C6A H6A 120.2 . . ? C1A C6A H6A 120.2 . . ? N1A C4A C3A 121.2(2) . . ? N1A C4A C5A 120.1(2) . . ? C3A C4A C5A 118.63(19) . . ? N3A C8A C9A 120.9(2) . . ? N3A C8A C11A 116.7(2) . . ? C9A C8A C11A 122.4(2) . . ? C8A C11A H11A 109.5 . . ? C8A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C8A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? N5A C14A H14D 109.5 . . ? N5A C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? N5A C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? C10A C9A C8A 117.2(2) . . ? C10A C9A H9A 121.4 . . ? C8A C9A H9A 121.4 . . ? N4 C10 C9 122.7(2) . . ? N4 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C10 C9 C8 117.5(2) . . ? C10 C9 H9 121.3 . . ? C8 C9 H9 121.3 . . ? C8 C11 H11D 109.5 . . ? C8 C11 H11E 109.5 . . ? H11D C11 H11E 109.5 . . ? C8 C11 H11F 109.5 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? N4A C10A C9A 123.0(2) . . ? N4A C10A H10A 118.5 . . ? C9A C10A H10A 118.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.445 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.059 #====END data_SM-DMA _database_code_depnum_ccdc_archive 'CCDC 840573' #TrackingRef 'SMZ-solvates-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Sulfamerazine-dimethylacetamide(1:1)' ; _chemical_name_common Sulfamerazine-dimethylacetamide(1:1) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 N5 O3 S' _chemical_formula_weight 351.44 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6792(15) _cell_length_b 8.3101(17) _cell_length_c 15.125(3) _cell_angle_alpha 93.13(3) _cell_angle_beta 101.81(3) _cell_angle_gamma 104.77(3) _cell_volume 907.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2608 _cell_measurement_theta_min 2.5510 _cell_measurement_theta_max 31.0677 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9167 _exptl_absorpt_correction_T_max 0.9366 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13429 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4440 _reflns_number_gt 4184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0857P)^2^+0.7409P] 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_number_reflns 4440 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1661 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.001 _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 0.32539(6) -0.02839(6) 0.27193(3) 0.02508(16) Uani 1 1 d . . . N2 N 0.3561(2) -0.0637(2) 0.37956(12) 0.0257(4) Uani 1 1 d . . . O2 O 0.5116(2) 0.0374(2) 0.26196(10) 0.0309(3) Uani 1 1 d . . . O1 O 0.2111(2) -0.17847(19) 0.21653(10) 0.0299(3) Uani 1 1 d . . . N4 N 0.2779(2) -0.1135(2) 0.51564(12) 0.0290(4) Uani 1 1 d . . . N3 N 0.0436(2) -0.1754(2) 0.37767(12) 0.0261(4) Uani 1 1 d . . . N1 N -0.0643(3) 0.4982(3) 0.23208(16) 0.0375(5) Uani 1 1 d . . . C1 C 0.2099(3) 0.1263(2) 0.25933(13) 0.0240(4) Uani 1 1 d . . . C5 C -0.0720(3) 0.2071(3) 0.21315(13) 0.0263(4) Uani 1 1 d . . . H5 H -0.2012 0.1777 0.1876 0.032 Uiso 1 1 calc R . . C7 C 0.2171(3) -0.1203(2) 0.42541(13) 0.0241(4) Uani 1 1 d . . . C3 C 0.2174(3) 0.4176(3) 0.27852(14) 0.0289(4) Uani 1 1 d . . . H3 H 0.2844 0.5311 0.2982 0.035 Uiso 1 1 calc R . . C6 C 0.0193(3) 0.0835(3) 0.22295(13) 0.0259(4) Uani 1 1 d . . . H6 H -0.0474 -0.0305 0.2050 0.031 Uiso 1 1 calc R . . C8 C -0.0864(3) -0.2324(3) 0.42476(15) 0.0290(4) Uani 1 1 d . . . C4 C 0.0255(3) 0.3767(3) 0.24080(13) 0.0265(4) Uani 1 1 d . . . C2 C 0.3086(3) 0.2935(3) 0.28711(13) 0.0274(4) Uani 1 1 d . . . H2 H 0.4381 0.3221 0.3118 0.033 Uiso 1 1 calc R . . C9 C -0.0383(3) -0.2336(3) 0.51836(16) 0.0360(5) Uani 1 1 d . . . H9 H -0.1291 -0.2751 0.5518 0.043 Uiso 1 1 calc R . . O3 O 0.5677(3) 0.3993(3) 0.12761(14) 0.0524(5) Uani 1 1 d . . . C10 C 0.1458(3) -0.1724(3) 0.56090(15) 0.0362(5) Uani 1 1 d . . . H10 H 0.1809 -0.1717 0.6249 0.043 Uiso 1 1 calc R . . N5 N 0.2881(3) 0.2977(4) 0.03959(16) 0.0557(7) Uani 1 1 d . . . C12 C 0.4182(4) 0.4203(4) 0.08888(18) 0.0502(7) Uani 1 1 d . . . C11 C -0.2819(3) -0.2922(3) 0.37075(17) 0.0384(5) Uani 1 1 d . . . H11A H -0.3122 -0.2038 0.3353 0.058 Uiso 1 1 calc R . . H11B H -0.3655 -0.3198 0.4121 0.058 Uiso 1 1 calc R . . H11C H -0.2960 -0.3921 0.3295 0.058 Uiso 1 1 calc R . . C14 C 0.1053(4) 0.3051(4) -0.00992(19) 0.0514(7) Uani 1 1 d . . . H14A H 0.0236 0.3006 0.0324 0.077 Uiso 1 1 calc R . . H14B H 0.0528 0.2099 -0.0574 0.077 Uiso 1 1 calc R . . H14C H 0.1174 0.4099 -0.0379 0.077 Uiso 1 1 calc R . . C13 C 0.3679(5) 0.5849(4) 0.0925(2) 0.0596(8) Uani 1 1 d . . . H13A H 0.4704 0.6710 0.1319 0.089 Uiso 1 1 calc R . . H13B H 0.2568 0.5714 0.1168 0.089 Uiso 1 1 calc R . . H13C H 0.3441 0.6189 0.0311 0.089 Uiso 1 1 calc R . . C15 C 0.3275(5) 0.1252(4) 0.0350(2) 0.0572(8) Uani 1 1 d . . . H15A H 0.4467 0.1323 0.0759 0.086 Uiso 1 1 calc R . . H15B H 0.3314 0.0907 -0.0274 0.086 Uiso 1 1 calc R . . H15C H 0.2294 0.0428 0.0536 0.086 Uiso 1 1 calc R . . H4 H -0.168(5) 0.474(4) 0.204(2) 0.050(9) Uiso 1 1 d . . . H7 H 0.458(5) -0.013(4) 0.412(2) 0.046(8) Uiso 1 1 d . . . H1 H 0.004(5) 0.607(4) 0.245(2) 0.054(9) 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 0.0231(3) 0.0320(3) 0.0215(2) 0.00426(18) 0.00677(18) 0.00816(19) N2 0.0200(8) 0.0360(9) 0.0214(8) 0.0067(7) 0.0055(6) 0.0065(7) O2 0.0242(7) 0.0435(9) 0.0285(7) 0.0095(6) 0.0111(6) 0.0104(6) O1 0.0323(8) 0.0316(7) 0.0264(7) -0.0001(6) 0.0069(6) 0.0101(6) N4 0.0246(8) 0.0375(9) 0.0238(8) 0.0053(7) 0.0071(7) 0.0048(7) N3 0.0222(8) 0.0290(8) 0.0267(8) 0.0022(6) 0.0065(6) 0.0058(6) N1 0.0310(10) 0.0313(10) 0.0464(12) -0.0002(8) -0.0005(9) 0.0100(8) C1 0.0233(9) 0.0283(9) 0.0207(8) 0.0047(7) 0.0065(7) 0.0058(7) C5 0.0216(9) 0.0316(10) 0.0235(9) 0.0017(7) 0.0043(7) 0.0039(7) C7 0.0233(9) 0.0258(9) 0.0248(9) 0.0036(7) 0.0079(7) 0.0073(7) C3 0.0264(10) 0.0285(10) 0.0284(9) 0.0032(8) 0.0042(8) 0.0029(8) C6 0.0235(9) 0.0281(9) 0.0238(9) 0.0018(7) 0.0049(7) 0.0037(7) C8 0.0243(10) 0.0303(10) 0.0327(10) 0.0011(8) 0.0095(8) 0.0061(8) C4 0.0275(10) 0.0287(10) 0.0234(9) 0.0041(7) 0.0061(7) 0.0075(8) C2 0.0217(9) 0.0330(10) 0.0245(9) 0.0039(8) 0.0036(7) 0.0032(8) C9 0.0287(11) 0.0446(13) 0.0341(11) 0.0050(9) 0.0145(9) 0.0030(9) O3 0.0305(9) 0.0793(15) 0.0450(10) 0.0097(10) 0.0028(8) 0.0143(9) C10 0.0321(11) 0.0488(13) 0.0268(10) 0.0074(9) 0.0114(9) 0.0047(10) N5 0.0414(13) 0.0855(19) 0.0336(11) 0.0097(11) 0.0052(9) 0.0076(12) C12 0.0431(14) 0.0734(19) 0.0348(12) 0.0088(12) 0.0132(11) 0.0129(13) C11 0.0241(10) 0.0453(13) 0.0421(12) -0.0014(10) 0.0082(9) 0.0038(9) C14 0.0382(14) 0.0712(19) 0.0388(13) 0.0074(13) 0.0002(11) 0.0109(13) C13 0.086(2) 0.0533(17) 0.0571(18) 0.0124(14) 0.0434(17) 0.0275(16) C15 0.080(2) 0.0468(15) 0.0444(15) 0.0049(12) 0.0194(15) 0.0127(15) _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 1.4334(17) . ? S1 O2 1.4374(15) . ? S1 N2 1.6498(17) . ? S1 C1 1.736(2) . ? N2 C7 1.387(2) . ? N2 H7 0.83(3) . ? N4 C7 1.342(3) . ? N4 C10 1.343(3) . ? N3 C7 1.329(3) . ? N3 C8 1.347(3) . ? N1 C4 1.358(3) . ? N1 H4 0.79(3) . ? N1 H1 0.91(3) . ? C1 C2 1.397(3) . ? C1 C6 1.398(3) . ? C5 C6 1.382(3) . ? C5 C4 1.410(3) . ? C5 H5 0.9500 . ? C3 C2 1.384(3) . ? C3 C4 1.411(3) . ? C3 H3 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.389(3) . ? C8 C11 1.497(3) . ? C2 H2 0.9500 . ? C9 C10 1.377(3) . ? C9 H9 0.9500 . ? O3 C12 1.237(4) . ? C10 H10 0.9500 . ? N5 C12 1.299(4) . ? N5 C14 1.468(4) . ? N5 C15 1.539(4) . ? C12 C13 1.514(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 119.06(10) . . ? O1 S1 N2 108.88(10) . . ? O2 S1 N2 102.53(9) . . ? O1 S1 C1 108.76(9) . . ? O2 S1 C1 109.61(10) . . ? N2 S1 C1 107.33(9) . . ? C7 N2 S1 125.79(15) . . ? C7 N2 H7 115(2) . . ? S1 N2 H7 115(2) . . ? C7 N4 C10 114.88(18) . . ? C7 N3 C8 116.58(18) . . ? C4 N1 H4 119(2) . . ? C4 N1 H1 118(2) . . ? H4 N1 H1 121(3) . . ? C2 C1 C6 120.35(19) . . ? C2 C1 S1 119.39(15) . . ? C6 C1 S1 120.25(15) . . ? C6 C5 C4 120.43(18) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? N3 C7 N4 127.37(18) . . ? N3 C7 N2 118.62(18) . . ? N4 C7 N2 114.01(18) . . ? C2 C3 C4 120.49(19) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C6 C1 120.02(18) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N3 C8 C9 120.8(2) . . ? N3 C8 C11 116.3(2) . . ? C9 C8 C11 122.9(2) . . ? N1 C4 C5 120.5(2) . . ? N1 C4 C3 120.6(2) . . ? C5 C4 C3 118.87(19) . . ? C3 C2 C1 119.84(19) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C10 C9 C8 117.6(2) . . ? C10 C9 H9 121.2 . . ? C8 C9 H9 121.2 . . ? N4 C10 C9 122.7(2) . . ? N4 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? C12 N5 C14 126.8(3) . . ? C12 N5 C15 116.6(3) . . ? C14 N5 C15 116.6(3) . . ? O3 C12 N5 121.2(3) . . ? O3 C12 C13 125.1(3) . . ? N5 C12 C13 113.7(3) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N5 C14 H14A 109.5 . . ? N5 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N5 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N5 C15 H15A 109.5 . . ? N5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.594 _refine_diff_density_min -0.532 _refine_diff_density_rms 0.068 #====END data_SM-CP(1:1) _database_code_depnum_ccdc_archive 'CCDC 840574' #TrackingRef 'SMZ-solvates-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Sulfamerazine-cyclopentanone(1:1)' ; _chemical_name_common Sulfamerazine-cyclopentanone(1:1) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 N4 O3 S' _chemical_formula_weight 348.42 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9650(12) _cell_length_b 9.6479(19) _cell_length_c 14.817(3) _cell_angle_alpha 76.16(3) _cell_angle_beta 83.05(3) _cell_angle_gamma 89.71(3) _cell_volume 821.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2357 _cell_measurement_theta_min 2.1747 _cell_measurement_theta_max 30.9798 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9094 _exptl_absorpt_correction_T_max 0.9623 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11686 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4004 _reflns_number_gt 3825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0598P)^2^+1.2728P] 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_number_reflns 4004 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1576 _refine_ls_wR_factor_gt 0.1564 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _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 0.09200(9) 0.77141(5) 0.20977(4) 0.01864(16) Uani 1 1 d . . . O1 O 0.3125(3) 0.78348(18) 0.23675(11) 0.0237(4) Uani 1 1 d . . . O2 O -0.0933(3) 0.84173(17) 0.25059(11) 0.0237(4) Uani 1 1 d . . . N2 N 0.0914(3) 0.8413(2) 0.09735(13) 0.0207(4) Uani 1 1 d . . . N3 N 0.4164(3) 0.7355(2) 0.03958(13) 0.0209(4) Uani 1 1 d . . . N4 N 0.2514(3) 0.9417(2) -0.05209(13) 0.0204(4) Uani 1 1 d . . . N1 N -0.1418(4) 0.1568(2) 0.29153(17) 0.0282(5) Uani 1 1 d . . . C2 C -0.1882(4) 0.5466(2) 0.21502(15) 0.0201(4) Uani 1 1 d . . . H2 H -0.2950 0.6152 0.1918 0.024 Uiso 1 1 calc R . . C1 C 0.0239(4) 0.5903(2) 0.23038(14) 0.0184(4) Uani 1 1 d . . . C4 C -0.0870(4) 0.2994(2) 0.27065(15) 0.0202(4) Uani 1 1 d . . . C5 C 0.1232(4) 0.3458(2) 0.28693(15) 0.0207(4) Uani 1 1 d . . . H5 H 0.2286 0.2778 0.3124 0.025 Uiso 1 1 calc R . . C7 C 0.2637(4) 0.8381(2) 0.02556(15) 0.0190(4) Uani 1 1 d . . . C6 C 0.1783(4) 0.4901(2) 0.26614(15) 0.0203(4) Uani 1 1 d . . . H6 H 0.3222 0.5206 0.2764 0.024 Uiso 1 1 calc R . . C10 C 0.4176(4) 0.9447(2) -0.12207(16) 0.0219(4) Uani 1 1 d . . . H10 H 0.4183 1.0167 -0.1785 0.026 Uiso 1 1 calc R . . C8 C 0.5799(4) 0.7400(2) -0.03258(16) 0.0220(4) Uani 1 1 d . . . C3 C -0.2410(4) 0.4021(2) 0.23400(16) 0.0218(4) Uani 1 1 d . . . H3 H -0.3835 0.3719 0.2221 0.026 Uiso 1 1 calc R . . C9 C 0.5881(4) 0.8464(3) -0.11495(16) 0.0242(5) Uani 1 1 d . . . H9 H 0.7067 0.8514 -0.1647 0.029 Uiso 1 1 calc R . . C11 C 0.7529(4) 0.6255(3) -0.02076(18) 0.0283(5) Uani 1 1 d . . . H11A H 0.8856 0.6597 0.0014 0.042 Uiso 1 1 calc R . . H11B H 0.7979 0.6018 -0.0810 0.042 Uiso 1 1 calc R . . H11C H 0.6882 0.5401 0.0251 0.042 Uiso 1 1 calc R . . O3 O 0.2828(5) 1.0231(2) 0.36361(16) 0.0462(6) Uani 1 1 d . . . C12 C 0.5370(4) 0.8454(3) 0.43321(17) 0.0262(5) Uani 1 1 d . . . H12A H 0.6297 0.9149 0.4531 0.031 Uiso 1 1 calc R . . H12B H 0.6195 0.8210 0.3772 0.031 Uiso 1 1 calc R . . C13 C 0.4843(5) 0.7123(3) 0.51194(18) 0.0301(5) Uani 1 1 d . . . H13A H 0.4725 0.7354 0.5739 0.036 Uiso 1 1 calc R . . H13B H 0.6018 0.6401 0.5091 0.036 Uiso 1 1 calc R . . C16 C 0.3109(5) 0.9053(3) 0.41283(17) 0.0273(5) Uani 1 1 d . . . C15 C 0.1292(4) 0.7965(3) 0.46240(19) 0.0341(6) Uani 1 1 d . . . H15A H 0.0199 0.7842 0.4195 0.041 Uiso 1 1 calc R . . H15B H 0.0469 0.8251 0.5169 0.041 Uiso 1 1 calc R . . C14 C 0.2573(5) 0.6592(3) 0.49373(19) 0.0351(6) Uani 1 1 d . . . H14A H 0.1769 0.5967 0.5514 0.042 Uiso 1 1 calc R . . H14B H 0.2774 0.6058 0.4440 0.042 Uiso 1 1 calc R . . H1 H -0.273(7) 0.135(4) 0.286(3) 0.044(10) Uiso 1 1 d . . . H7 H -0.016(6) 0.896(4) 0.083(2) 0.041(9) Uiso 1 1 d . . . H4 H -0.039(7) 0.095(4) 0.313(3) 0.050(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 0.0220(3) 0.0163(3) 0.0165(3) -0.00240(19) -0.00103(19) -0.00034(19) O1 0.0257(9) 0.0230(8) 0.0219(8) -0.0036(6) -0.0047(6) -0.0047(6) O2 0.0287(9) 0.0215(8) 0.0194(7) -0.0042(6) 0.0014(6) 0.0043(6) N2 0.0226(9) 0.0189(9) 0.0177(9) -0.0008(7) 0.0013(7) 0.0022(7) N3 0.0232(9) 0.0191(9) 0.0194(9) -0.0033(7) -0.0017(7) 0.0006(7) N4 0.0239(9) 0.0177(9) 0.0181(9) -0.0023(7) -0.0010(7) -0.0017(7) N1 0.0286(11) 0.0181(10) 0.0375(12) -0.0039(8) -0.0078(9) -0.0020(8) C2 0.0207(10) 0.0195(10) 0.0184(10) -0.0012(8) -0.0028(8) 0.0025(8) C1 0.0208(10) 0.0171(9) 0.0154(9) -0.0015(7) 0.0006(8) 0.0003(8) C4 0.0241(11) 0.0173(10) 0.0182(10) -0.0038(8) 0.0001(8) -0.0012(8) C5 0.0203(10) 0.0201(10) 0.0205(10) -0.0024(8) -0.0031(8) 0.0029(8) C7 0.0222(10) 0.0170(9) 0.0166(9) -0.0029(8) -0.0005(8) -0.0029(8) C6 0.0179(10) 0.0218(10) 0.0199(10) -0.0028(8) -0.0019(8) 0.0007(8) C10 0.0268(11) 0.0200(10) 0.0174(10) -0.0027(8) -0.0002(8) -0.0032(8) C8 0.0243(11) 0.0222(11) 0.0215(10) -0.0092(8) -0.0030(8) -0.0008(9) C3 0.0199(10) 0.0222(11) 0.0234(10) -0.0043(8) -0.0054(8) -0.0011(8) C9 0.0254(11) 0.0252(11) 0.0212(10) -0.0061(9) 0.0017(9) -0.0007(9) C11 0.0277(12) 0.0293(12) 0.0275(12) -0.0065(9) -0.0030(9) 0.0073(10) O3 0.0772(17) 0.0239(10) 0.0443(12) -0.0101(8) -0.0313(12) 0.0184(10) C12 0.0235(11) 0.0284(12) 0.0246(11) -0.0031(9) -0.0008(9) 0.0018(9) C13 0.0309(13) 0.0303(13) 0.0254(12) 0.0009(10) -0.0044(10) 0.0094(10) C16 0.0361(13) 0.0270(12) 0.0226(11) -0.0105(9) -0.0101(10) 0.0114(10) C15 0.0225(12) 0.0560(18) 0.0266(12) -0.0148(12) -0.0047(10) 0.0034(11) C14 0.0430(16) 0.0312(13) 0.0276(12) -0.0036(10) 0.0025(11) -0.0083(11) _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 1.4333(18) . ? S1 O2 1.4402(17) . ? S1 N2 1.641(2) . ? S1 C1 1.742(2) . ? N2 C7 1.393(3) . ? N2 H7 0.85(4) . ? N3 C7 1.338(3) . ? N3 C8 1.350(3) . ? N4 C10 1.340(3) . ? N4 C7 1.341(3) . ? N1 C4 1.368(3) . ? N1 H1 0.83(4) . ? N1 H4 0.89(4) . ? C2 C3 1.385(3) . ? C2 C1 1.397(3) . ? C2 H2 0.9500 . ? C1 C6 1.388(3) . ? C4 C5 1.400(3) . ? C4 C3 1.405(3) . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C10 C9 1.383(3) . ? C10 H10 0.9500 . ? C8 C9 1.390(3) . ? C8 C11 1.502(3) . ? C3 H3 0.9500 . ? C9 H9 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O3 C16 1.218(3) . ? C12 C16 1.500(3) . ? C12 C13 1.519(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.526(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C16 C15 1.506(4) . ? C15 C14 1.528(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 119.11(10) . . ? O1 S1 N2 110.78(11) . . ? O2 S1 N2 102.22(10) . . ? O1 S1 C1 107.66(11) . . ? O2 S1 C1 109.01(11) . . ? N2 S1 C1 107.50(11) . . ? C7 N2 S1 127.31(17) . . ? C7 N2 H7 116(2) . . ? S1 N2 H7 116(2) . . ? C7 N3 C8 115.59(19) . . ? C10 N4 C7 115.3(2) . . ? C4 N1 H1 117(3) . . ? C4 N1 H4 119(3) . . ? H1 N1 H4 124(4) . . ? C3 C2 C1 119.3(2) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C6 C1 C2 120.4(2) . . ? C6 C1 S1 119.39(18) . . ? C2 C1 S1 120.16(17) . . ? N1 C4 C5 120.4(2) . . ? N1 C4 C3 120.9(2) . . ? C5 C4 C3 118.7(2) . . ? C6 C5 C4 120.4(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? N3 C7 N4 127.7(2) . . ? N3 C7 N2 118.84(19) . . ? N4 C7 N2 113.5(2) . . ? C5 C6 C1 120.2(2) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? N4 C10 C9 122.2(2) . . ? N4 C10 H10 118.9 . . ? C9 C10 H10 118.9 . . ? N3 C8 C9 121.4(2) . . ? N3 C8 C11 117.5(2) . . ? C9 C8 C11 121.1(2) . . ? C2 C3 C4 121.0(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C10 C9 C8 117.7(2) . . ? C10 C9 H9 121.1 . . ? C8 C9 H9 121.1 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C16 C12 C13 105.0(2) . . ? C16 C12 H12A 110.8 . . ? C13 C12 H12A 110.8 . . ? C16 C12 H12B 110.8 . . ? C13 C12 H12B 110.8 . . ? H12A C12 H12B 108.8 . . ? C12 C13 C14 103.4(2) . . ? C12 C13 H13A 111.1 . . ? C14 C13 H13A 111.1 . . ? C12 C13 H13B 111.1 . . ? C14 C13 H13B 111.1 . . ? H13A C13 H13B 109.0 . . ? O3 C16 C12 124.6(3) . . ? O3 C16 C15 126.5(3) . . ? C12 C16 C15 109.0(2) . . ? C16 C15 C14 104.2(2) . . ? C16 C15 H15A 110.9 . . ? C14 C15 H15A 110.9 . . ? C16 C15 H15B 110.9 . . ? C14 C15 H15B 110.9 . . ? H15A C15 H15B 108.9 . . ? C13 C14 C15 103.6(2) . . ? C13 C14 H14A 111.1 . . ? C15 C14 H14A 111.1 . . ? C13 C14 H14B 111.1 . . ? C15 C14 H14B 111.1 . . ? H14A C14 H14B 109.0 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.588 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.079 #====END data_SM-3PC(1:1) _database_code_depnum_ccdc_archive 'CCDC 840575' #TrackingRef 'SMZ-solvates-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Sulfamerazine-3-Picoline(1:1)' ; _chemical_name_common Sulfamerazine-3-Picoline(1:1) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 N5 O2 S' _chemical_formula_weight 357.43 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8319(16) _cell_length_b 8.1117(16) _cell_length_c 15.358(3) _cell_angle_alpha 76.47(3) _cell_angle_beta 77.04(3) _cell_angle_gamma 73.54(3) _cell_volume 896.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2775 _cell_measurement_theta_min 2.6630 _cell_measurement_theta_max 30.7901 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9167 _exptl_absorpt_correction_T_max 0.9167 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13256 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4400 _reflns_number_gt 4195 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0598P)^2^+0.4494P] 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_number_reflns 4400 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.001 _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 1.00335(5) 0.57241(5) 0.27035(2) 0.02010(11) Uani 1 1 d . . . O1 O 0.93578(15) 0.73886(14) 0.21651(7) 0.0242(2) Uani 1 1 d . . . O2 O 1.19494(14) 0.49843(15) 0.25925(7) 0.0248(2) Uani 1 1 d . . . N2 N 0.95109(17) 0.58975(17) 0.37888(8) 0.0215(3) Uani 1 1 d . . . N3 N 0.64128(17) 0.70431(17) 0.37980(9) 0.0225(3) Uani 1 1 d . . . C1 C 0.89530(19) 0.42340(19) 0.25634(10) 0.0200(3) Uani 1 1 d . . . N4 N 0.76828(18) 0.61527(19) 0.51679(9) 0.0264(3) Uani 1 1 d . . . C5 C 0.6473(2) 0.3608(2) 0.21255(10) 0.0221(3) Uani 1 1 d . . . H5 H 0.5388 0.4002 0.1878 0.027 Uiso 1 1 calc R . . C4 C 0.7179(2) 0.1803(2) 0.24016(10) 0.0222(3) Uani 1 1 d . . . C2 C 0.9691(2) 0.2447(2) 0.28283(10) 0.0228(3) Uani 1 1 d . . . H2 H 1.0789 0.2061 0.3064 0.027 Uiso 1 1 calc R . . C7 C 0.7776(2) 0.63896(19) 0.42636(10) 0.0210(3) Uani 1 1 d . . . C13 C 0.2752(2) 0.9241(2) 0.04152(10) 0.0251(3) Uani 1 1 d . . . N1 N 0.6285(2) 0.06265(19) 0.23570(10) 0.0288(3) Uani 1 1 d . . . C6 C 0.7346(2) 0.48130(19) 0.22105(10) 0.0214(3) Uani 1 1 d . . . H6 H 0.6854 0.6029 0.2029 0.026 Uiso 1 1 calc R . . N5 N 0.33406(19) 1.0994(2) 0.13355(10) 0.0311(3) Uani 1 1 d . . . C14 C 0.1948(2) 1.0756(2) -0.01327(11) 0.0296(3) Uani 1 1 d . . . H14 H 0.1478 1.0685 -0.0638 0.035 Uiso 1 1 calc R . . C3 C 0.8818(2) 0.1247(2) 0.27451(11) 0.0248(3) Uani 1 1 d . . . H3 H 0.9326 0.0033 0.2921 0.030 Uiso 1 1 calc R . . C12 C 0.3423(2) 0.9452(2) 0.11374(11) 0.0282(3) Uani 1 1 d . . . H12 H 0.3978 0.8426 0.1517 0.034 Uiso 1 1 calc R . . C16 C 0.2541(2) 1.2434(2) 0.07987(12) 0.0313(4) Uani 1 1 d . . . H16 H 0.2456 1.3545 0.0931 0.038 Uiso 1 1 calc R . . C8 C 0.4755(2) 0.7511(2) 0.42868(11) 0.0261(3) Uani 1 1 d . . . C15 C 0.1835(2) 1.2370(2) 0.00624(12) 0.0320(4) Uani 1 1 d . . . H15 H 0.1281 1.3417 -0.0304 0.038 Uiso 1 1 calc R . . C9 C 0.4507(2) 0.7352(3) 0.52277(12) 0.0334(4) Uani 1 1 d . . . H9 H 0.3342 0.7705 0.5574 0.040 Uiso 1 1 calc R . . C11 C 0.3215(2) 0.8192(3) 0.37670(12) 0.0338(4) Uani 1 1 d . . . H11A H 0.3344 0.9289 0.3356 0.051 Uiso 1 1 calc R . . H11B H 0.2072 0.8402 0.4193 0.051 Uiso 1 1 calc R . . H11C H 0.3220 0.7330 0.3413 0.051 Uiso 1 1 calc R . . C17 C 0.2909(2) 0.7443(2) 0.02530(12) 0.0329(4) Uani 1 1 d . . . H17A H 0.1920 0.6974 0.0648 0.049 Uiso 1 1 calc R . . H17B H 0.4068 0.6675 0.0389 0.049 Uiso 1 1 calc R . . H17C H 0.2839 0.7509 -0.0384 0.049 Uiso 1 1 calc R . . C10 C 0.6020(2) 0.6661(3) 0.56371(11) 0.0335(4) Uani 1 1 d . . . H10 H 0.5877 0.6541 0.6278 0.040 Uiso 1 1 calc R . . H4 H 0.532(3) 0.099(3) 0.2053(15) 0.035(5) Uiso 1 1 d . . . H1 H 0.681(3) -0.049(3) 0.2464(15) 0.038(6) Uiso 1 1 d . . . H7 H 1.031(3) 0.531(3) 0.4103(16) 0.043(6) 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 0.01882(19) 0.02321(19) 0.01786(18) -0.00452(13) -0.00194(13) -0.00475(13) O1 0.0261(5) 0.0232(5) 0.0221(5) -0.0020(4) -0.0033(4) -0.0067(4) O2 0.0182(5) 0.0329(6) 0.0231(5) -0.0079(4) -0.0012(4) -0.0053(4) N2 0.0176(6) 0.0284(6) 0.0178(6) -0.0061(5) -0.0034(5) -0.0028(5) N3 0.0199(6) 0.0243(6) 0.0218(6) -0.0031(5) -0.0029(5) -0.0044(5) C1 0.0197(6) 0.0212(6) 0.0187(6) -0.0051(5) -0.0028(5) -0.0036(5) N4 0.0228(6) 0.0339(7) 0.0203(6) -0.0056(5) -0.0033(5) -0.0029(5) C5 0.0191(7) 0.0256(7) 0.0207(7) -0.0034(5) -0.0050(5) -0.0033(5) C4 0.0226(7) 0.0250(7) 0.0188(6) -0.0058(5) -0.0021(5) -0.0052(6) C2 0.0192(7) 0.0240(7) 0.0241(7) -0.0050(5) -0.0059(5) -0.0011(5) C7 0.0211(7) 0.0217(6) 0.0200(6) -0.0043(5) -0.0013(5) -0.0061(5) C13 0.0214(7) 0.0313(8) 0.0215(7) -0.0056(6) 0.0007(6) -0.0077(6) N1 0.0295(7) 0.0239(7) 0.0356(7) -0.0030(5) -0.0128(6) -0.0069(6) C6 0.0212(7) 0.0215(7) 0.0193(6) -0.0037(5) -0.0035(5) -0.0015(5) N5 0.0263(7) 0.0380(8) 0.0313(7) -0.0129(6) -0.0059(6) -0.0052(6) C14 0.0266(8) 0.0397(9) 0.0217(7) -0.0019(6) -0.0053(6) -0.0090(7) C3 0.0250(7) 0.0207(7) 0.0269(7) -0.0045(5) -0.0062(6) -0.0012(6) C12 0.0253(8) 0.0324(8) 0.0245(7) -0.0050(6) -0.0047(6) -0.0032(6) C16 0.0274(8) 0.0317(8) 0.0343(9) -0.0109(7) 0.0005(7) -0.0072(6) C8 0.0220(7) 0.0276(7) 0.0252(7) -0.0022(6) -0.0029(6) -0.0036(6) C15 0.0286(8) 0.0315(8) 0.0299(8) 0.0003(6) -0.0019(6) -0.0050(7) C9 0.0216(8) 0.0455(10) 0.0259(8) -0.0055(7) 0.0005(6) -0.0010(7) C11 0.0220(7) 0.0434(10) 0.0308(8) -0.0004(7) -0.0053(6) -0.0043(7) C17 0.0339(9) 0.0363(9) 0.0300(8) -0.0095(7) 0.0004(7) -0.0127(7) C10 0.0269(8) 0.0476(10) 0.0196(7) -0.0061(7) -0.0002(6) -0.0021(7) _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 1.4338(12) . ? S1 O2 1.4365(12) . ? S1 N2 1.6542(13) . ? S1 C1 1.7340(15) . ? N2 C7 1.3864(19) . ? N2 H7 0.84(2) . ? N3 C7 1.333(2) . ? N3 C8 1.345(2) . ? C1 C6 1.396(2) . ? C1 C2 1.398(2) . ? N4 C10 1.341(2) . ? N4 C7 1.3449(19) . ? C5 C6 1.385(2) . ? C5 C4 1.408(2) . ? C5 H5 0.9500 . ? C4 N1 1.356(2) . ? C4 C3 1.412(2) . ? C2 C3 1.381(2) . ? C2 H2 0.9500 . ? C13 C14 1.389(2) . ? C13 C12 1.391(2) . ? C13 C17 1.503(2) . ? N1 H4 0.92(2) . ? N1 H1 0.88(2) . ? C6 H6 0.9500 . ? N5 C12 1.336(2) . ? N5 C16 1.343(2) . ? C14 C15 1.385(3) . ? C14 H14 0.9500 . ? C3 H3 0.9500 . ? C12 H12 0.9500 . ? C16 C15 1.382(3) . ? C16 H16 0.9500 . ? C8 C9 1.394(2) . ? C8 C11 1.499(2) . ? C15 H15 0.9500 . ? C9 C10 1.381(2) . ? C9 H9 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C10 H10 0.9500 . ? 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 118.89(7) . . ? O1 S1 N2 109.00(7) . . ? O2 S1 N2 102.55(7) . . ? O1 S1 C1 108.78(7) . . ? O2 S1 C1 109.70(7) . . ? N2 S1 C1 107.26(7) . . ? C7 N2 S1 125.50(11) . . ? C7 N2 H7 116.1(16) . . ? S1 N2 H7 114.6(16) . . ? C7 N3 C8 116.45(13) . . ? C6 C1 C2 120.52(14) . . ? C6 C1 S1 120.41(11) . . ? C2 C1 S1 119.05(11) . . ? C10 N4 C7 115.01(14) . . ? C6 C5 C4 120.66(13) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? N1 C4 C5 120.74(14) . . ? N1 C4 C3 120.62(14) . . ? C5 C4 C3 118.62(14) . . ? C3 C2 C1 119.72(14) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? N3 C7 N4 127.32(14) . . ? N3 C7 N2 118.55(13) . . ? N4 C7 N2 114.13(13) . . ? C14 C13 C12 116.85(15) . . ? C14 C13 C17 122.72(15) . . ? C12 C13 C17 120.43(15) . . ? C4 N1 H4 119.3(14) . . ? C4 N1 H1 119.3(15) . . ? H4 N1 H1 119(2) . . ? C5 C6 C1 119.73(13) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C12 N5 C16 117.14(15) . . ? C15 C14 C13 119.60(16) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C2 C3 C4 120.73(14) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? N5 C12 C13 124.65(16) . . ? N5 C12 H12 117.7 . . ? C13 C12 H12 117.7 . . ? N5 C16 C15 122.81(16) . . ? N5 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? N3 C8 C9 121.02(15) . . ? N3 C8 C11 116.48(14) . . ? C9 C8 C11 122.49(15) . . ? C16 C15 C14 118.95(16) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C10 C9 C8 117.43(15) . . ? C10 C9 H9 121.3 . . ? C8 C9 H9 121.3 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N4 C10 C9 122.74(15) . . ? N4 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.307 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.057 #====END