# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Hongyu Zhang' _publ_contact_author_email hongyuzhang@jlu.edu.cn loop_ _publ_author_name 'Dandan Yao' 'Shanshan Zhao' 'Jianhua Guo' 'Zuolun Zhang' 'Hongyu Zhang' 'Yu Liu' 'Yue Wang' data_mCzOH _database_code_depnum_ccdc_archive 'CCDC 805257' #TrackingRef 'crystal data combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 N2 O S' _chemical_formula_weight 392.46 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 P2(1)/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 8.3907(4) _cell_length_b 30.6491(14) _cell_length_c 7.7677(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.2680(10) _cell_angle_gamma 90.00 _cell_volume 1927.09(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4779 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9600 _exptl_absorpt_correction_T_max 0.9671 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 14128 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4779 _reflns_number_gt 3118 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0761P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4779 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 C1 C -0.3249(2) -0.03184(6) 0.1065(3) 0.0464(5) Uani 1 1 d . . . C2 C -0.4046(3) -0.06555(7) -0.0038(3) 0.0557(6) Uani 1 1 d . . . H2 H -0.3868 -0.0703 -0.1155 0.067 Uiso 1 1 calc R . . C3 C -0.5106(3) -0.09150(7) 0.0592(4) 0.0602(6) Uani 1 1 d . . . H3 H -0.5649 -0.1143 -0.0112 0.072 Uiso 1 1 calc R . . C4 C -0.5384(3) -0.08444(7) 0.2252(3) 0.0597(6) Uani 1 1 d . . . H4 H -0.6119 -0.1024 0.2631 0.072 Uiso 1 1 calc R . . C5 C -0.4594(3) -0.05140(7) 0.3352(3) 0.0558(6) Uani 1 1 d . . . H5 H -0.4788 -0.0468 0.4462 0.067 Uiso 1 1 calc R . . C6 C -0.3493(2) -0.02506(6) 0.2752(3) 0.0451(5) Uani 1 1 d . . . C7 C -0.1707(2) 0.02870(6) 0.2755(3) 0.0417(4) Uani 1 1 d . . . C8 C -0.0654(2) 0.06651(6) 0.3417(2) 0.0384(4) Uani 1 1 d . . . C9 C -0.0381(2) 0.07987(6) 0.5207(3) 0.0425(4) Uani 1 1 d . . . C10 C 0.0625(3) 0.11525(7) 0.5821(3) 0.0462(5) Uani 1 1 d . . . H10 H 0.0837 0.1233 0.7014 0.055 Uiso 1 1 calc R . . C11 C 0.1316(3) 0.13871(7) 0.4698(3) 0.0454(5) Uani 1 1 d . . . H11 H 0.1960 0.1631 0.5122 0.054 Uiso 1 1 calc R . . C12 C 0.1058(2) 0.12610(6) 0.2929(2) 0.0388(4) Uani 1 1 d . . . C13 C 0.0109(2) 0.08984(6) 0.2311(2) 0.0406(4) Uani 1 1 d . . . H13 H -0.0026 0.0808 0.1139 0.049 Uiso 1 1 calc R . . C14 C 0.3412(2) 0.16388(6) 0.2128(3) 0.0422(5) Uani 1 1 d . . . C15 C 0.4745(3) 0.14978(8) 0.3483(3) 0.0552(6) Uani 1 1 d . . . H15 H 0.4611 0.1300 0.4342 0.066 Uiso 1 1 calc R . . C16 C 0.6286(3) 0.16645(9) 0.3500(4) 0.0666(7) Uani 1 1 d . . . H16 H 0.7206 0.1575 0.4387 0.080 Uiso 1 1 calc R . . C17 C 0.6487(3) 0.19591(9) 0.2233(4) 0.0725(8) Uani 1 1 d . . . H17 H 0.7537 0.2066 0.2292 0.087 Uiso 1 1 calc R . . C18 C 0.5178(3) 0.20969(7) 0.0891(4) 0.0623(7) Uani 1 1 d . . . H18 H 0.5334 0.2297 0.0049 0.075 Uiso 1 1 calc R . . C19 C 0.3599(3) 0.19333(6) 0.0800(3) 0.0469(5) Uani 1 1 d . . . C20 C 0.1980(3) 0.19909(6) -0.0403(3) 0.0455(5) Uani 1 1 d . . . C21 C 0.1371(3) 0.22402(7) -0.1937(3) 0.0577(6) Uani 1 1 d . . . H21 H 0.2079 0.2412 -0.2390 0.069 Uiso 1 1 calc R . . C22 C -0.0286(4) 0.22287(8) -0.2768(3) 0.0654(7) Uani 1 1 d . . . H22 H -0.0698 0.2390 -0.3804 0.078 Uiso 1 1 calc R . . C23 C -0.1360(3) 0.19789(7) -0.2080(3) 0.0588(6) Uani 1 1 d . . . H23 H -0.2483 0.1984 -0.2651 0.071 Uiso 1 1 calc R . . C24 C -0.0808(3) 0.17257(6) -0.0583(3) 0.0466(5) Uani 1 1 d . . . H24 H -0.1531 0.1557 -0.0139 0.056 Uiso 1 1 calc R . . C25 C 0.0875(2) 0.17322(6) 0.0241(2) 0.0403(4) Uani 1 1 d . . . N1 N -0.2596(2) 0.00937(5) 0.3699(2) 0.0452(4) Uani 1 1 d . . . N2 N 0.17605(19) 0.15134(5) 0.1765(2) 0.0412(4) Uani 1 1 d . . . O1 O -0.1083(2) 0.05961(5) 0.63676(19) 0.0593(4) Uani 1 1 d . . . H1 H -0.1699 0.0402 0.5848 0.089 Uiso 1 1 calc R . . S1 S -0.18823(7) 0.006350(17) 0.06517(7) 0.04938(18) Uani 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 C1 0.0437(11) 0.0378(10) 0.0616(13) 0.0005(9) 0.0206(10) 0.0021(9) C2 0.0566(13) 0.0478(12) 0.0678(15) -0.0095(11) 0.0258(11) -0.0021(10) C3 0.0584(14) 0.0422(12) 0.0815(17) -0.0077(11) 0.0212(13) -0.0061(10) C4 0.0586(14) 0.0456(12) 0.0777(17) 0.0067(11) 0.0230(12) -0.0103(10) C5 0.0593(14) 0.0506(12) 0.0626(14) 0.0070(11) 0.0251(11) -0.0087(10) C6 0.0466(11) 0.0369(10) 0.0538(12) 0.0047(9) 0.0168(9) -0.0013(8) C7 0.0439(11) 0.0390(10) 0.0450(11) 0.0052(8) 0.0168(9) 0.0027(8) C8 0.0396(10) 0.0371(9) 0.0410(10) 0.0038(8) 0.0150(8) 0.0014(8) C9 0.0434(11) 0.0454(11) 0.0429(11) 0.0072(9) 0.0189(9) 0.0040(9) C10 0.0505(12) 0.0541(12) 0.0363(10) -0.0048(9) 0.0153(9) 0.0001(10) C11 0.0467(11) 0.0456(11) 0.0460(11) -0.0073(9) 0.0159(9) -0.0077(9) C12 0.0379(10) 0.0401(10) 0.0411(10) 0.0026(8) 0.0151(8) -0.0004(8) C13 0.0451(11) 0.0415(10) 0.0375(10) 0.0006(8) 0.0148(8) -0.0015(8) C14 0.0443(11) 0.0385(10) 0.0472(11) -0.0103(8) 0.0178(9) -0.0077(8) C15 0.0491(13) 0.0629(14) 0.0529(13) -0.0089(11) 0.0124(10) -0.0078(10) C16 0.0440(13) 0.0796(17) 0.0736(17) -0.0278(14) 0.0112(12) -0.0117(12) C17 0.0543(16) 0.0723(17) 0.099(2) -0.0347(16) 0.0357(16) -0.0253(13) C18 0.0717(17) 0.0462(12) 0.0830(17) -0.0154(12) 0.0452(15) -0.0194(11) C19 0.0580(13) 0.0360(10) 0.0548(12) -0.0122(9) 0.0290(10) -0.0114(9) C20 0.0655(14) 0.0310(9) 0.0481(12) -0.0041(8) 0.0292(10) -0.0049(9) C21 0.0875(19) 0.0382(11) 0.0565(13) 0.0061(10) 0.0351(13) 0.0006(11) C22 0.101(2) 0.0481(13) 0.0496(13) 0.0101(10) 0.0247(14) 0.0196(13) C23 0.0675(15) 0.0560(13) 0.0492(13) -0.0018(10) 0.0086(11) 0.0164(11) C24 0.0509(12) 0.0455(11) 0.0453(11) -0.0039(9) 0.0160(9) 0.0003(9) C25 0.0521(12) 0.0341(9) 0.0383(10) -0.0035(8) 0.0179(9) -0.0021(8) N1 0.0495(10) 0.0413(9) 0.0484(10) 0.0030(7) 0.0195(8) -0.0064(8) N2 0.0420(9) 0.0420(8) 0.0406(9) 0.0027(7) 0.0128(7) -0.0083(7) O1 0.0706(11) 0.0672(11) 0.0482(9) 0.0030(7) 0.0299(8) -0.0121(8) S1 0.0519(3) 0.0485(3) 0.0552(3) -0.0046(2) 0.0271(3) -0.0054(2) _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 C1 C6 1.393(3) . ? C1 C2 1.396(3) . ? C1 S1 1.727(2) . ? C2 C3 1.376(3) . ? C2 H2 0.9300 . ? C3 C4 1.386(3) . ? C3 H3 0.9300 . ? C4 C5 1.377(3) . ? C4 H4 0.9300 . ? C5 C6 1.396(3) . ? C5 H5 0.9300 . ? C6 N1 1.389(3) . ? C7 N1 1.317(2) . ? C7 C8 1.466(3) . ? C7 S1 1.741(2) . ? C8 C13 1.396(3) . ? C8 C9 1.409(3) . ? C9 O1 1.351(2) . ? C9 C10 1.380(3) . ? C10 C11 1.372(3) . ? C10 H10 0.9300 . ? C11 C12 1.388(3) . ? C11 H11 0.9300 . ? C12 C13 1.378(3) . ? C12 N2 1.430(2) . ? C13 H13 0.9300 . ? C14 C15 1.387(3) . ? C14 N2 1.394(2) . ? C14 C19 1.410(3) . ? C15 C16 1.388(3) . ? C15 H15 0.9300 . ? C16 C17 1.378(4) . ? C16 H16 0.9300 . ? C17 C18 1.367(4) . ? C17 H17 0.9300 . ? C18 C19 1.401(3) . ? C18 H18 0.9300 . ? C19 C20 1.442(3) . ? C20 C21 1.395(3) . ? C20 C25 1.408(3) . ? C21 C22 1.370(3) . ? C21 H21 0.9300 . ? C22 C23 1.392(3) . ? C22 H22 0.9300 . ? C23 C24 1.373(3) . ? C23 H23 0.9300 . ? C24 C25 1.389(3) . ? C24 H24 0.9300 . ? C25 N2 1.393(2) . ? O1 H1 0.8200 . ? 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 C6 C1 C2 121.52(19) . . ? C6 C1 S1 110.04(15) . . ? C2 C1 S1 128.44(18) . . ? C3 C2 C1 117.3(2) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C2 C3 C4 121.6(2) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 121.4(2) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.1(2) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? N1 C6 C1 114.72(18) . . ? N1 C6 C5 125.2(2) . . ? C1 C6 C5 120.1(2) . . ? N1 C7 C8 122.53(18) . . ? N1 C7 S1 115.16(15) . . ? C8 C7 S1 122.31(14) . . ? C13 C8 C9 118.51(17) . . ? C13 C8 C7 121.34(17) . . ? C9 C8 C7 120.15(17) . . ? O1 C9 C10 117.71(18) . . ? O1 C9 C8 122.61(18) . . ? C10 C9 C8 119.68(18) . . ? C11 C10 C9 120.97(18) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 120.11(18) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 119.65(17) . . ? C13 C12 N2 120.85(17) . . ? C11 C12 N2 119.49(17) . . ? C12 C13 C8 120.99(18) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C15 C14 N2 128.87(19) . . ? C15 C14 C19 122.1(2) . . ? N2 C14 C19 108.92(18) . . ? C14 C15 C16 117.1(2) . . ? C14 C15 H15 121.4 . . ? C16 C15 H15 121.4 . . ? C17 C16 C15 121.5(2) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C18 C17 C16 121.5(2) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C19 119.1(2) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C14 118.5(2) . . ? C18 C19 C20 134.9(2) . . ? C14 C19 C20 106.58(17) . . ? C21 C20 C25 119.0(2) . . ? C21 C20 C19 133.7(2) . . ? C25 C20 C19 107.29(17) . . ? C22 C21 C20 119.1(2) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 120.8(2) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C24 C23 C22 121.9(2) . . ? C24 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? C23 C24 C25 117.2(2) . . ? C23 C24 H24 121.4 . . ? C25 C24 H24 121.4 . . ? C24 C25 N2 129.38(18) . . ? C24 C25 C20 121.99(18) . . ? N2 C25 C20 108.61(17) . . ? C7 N1 C6 110.74(17) . . ? C25 N2 C14 108.58(15) . . ? C25 N2 C12 125.56(16) . . ? C14 N2 C12 125.10(16) . . ? C9 O1 H1 109.5 . . ? C1 S1 C7 89.33(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.255 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.058 #===end data_mMeOH _database_code_depnum_ccdc_archive 'CCDC 805258' #TrackingRef 'crystal data combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 N2 O S' _chemical_formula_weight 270.34 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.9711(14) _cell_length_b 11.626(2) _cell_length_c 16.440(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.97(3) _cell_angle_gamma 90.00 _cell_volume 1332.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3040 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 20.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9533 _exptl_absorpt_correction_T_max 0.9590 _exptl_absorpt_process_details ? _exptl_special_details ; Higash,T(1995) Progrom for Absorption Correcttion. Rigaku Corporation,Tokyo,Japan. ; _diffrn_ambient_temperature 293(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 'Omega scan' _diffrn_measurement_method 10.0 _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 12828 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3040 _reflns_number_gt 2017 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1058P)^2^+0.1003P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3040 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0864 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 C1 C 0.2221(4) -0.0602(2) 0.63249(15) 0.0541(6) Uani 1 1 d . . . C2 C 0.0736(5) -0.1366(2) 0.64982(17) 0.0674(8) Uani 1 1 d . . . H2 H -0.0448 -0.1324 0.6230 0.081 Uiso 1 1 calc R . . C3 C 0.1115(5) -0.2194(3) 0.70930(18) 0.0749(9) Uani 1 1 d . . . H3 H 0.0158 -0.2715 0.7227 0.090 Uiso 1 1 calc R . . C4 C 0.2850(6) -0.2259(3) 0.74826(17) 0.0730(9) Uani 1 1 d . . . H4 H 0.3055 -0.2833 0.7869 0.088 Uiso 1 1 calc R . . C5 C 0.4322(5) -0.1494(2) 0.73206(16) 0.0644(7) Uani 1 1 d . . . H5 H 0.5499 -0.1535 0.7594 0.077 Uiso 1 1 calc R . . C6 C 0.3958(4) -0.0665(2) 0.67333(15) 0.0537(6) Uani 1 1 d . . . C7 C 0.4592(4) 0.0837(2) 0.59317(14) 0.0495(6) Uani 1 1 d . . . C8 C 0.5626(4) 0.1797(2) 0.55886(14) 0.0504(6) Uani 1 1 d . . . C9 C 0.7460(4) 0.2067(2) 0.58853(17) 0.0626(7) Uani 1 1 d . . . C10 C 0.8448(5) 0.2977(3) 0.55438(19) 0.0754(9) Uani 1 1 d . . . H10 H 0.9681 0.3146 0.5732 0.090 Uiso 1 1 calc R . . C11 C 0.7649(5) 0.3630(3) 0.49368(19) 0.0741(9) Uani 1 1 d . . . H11 H 0.8345 0.4237 0.4721 0.089 Uiso 1 1 calc R . . C12 C 0.5774(5) 0.3400(2) 0.46300(16) 0.0621(7) Uani 1 1 d . . . C13 C 0.4821(4) 0.2470(2) 0.49647(14) 0.0569(6) Uani 1 1 d . . . H13 H 0.3600 0.2288 0.4767 0.068 Uiso 1 1 calc R . . C14 C 0.6027(6) 0.4973(3) 0.3644(2) 0.0979(13) Uani 1 1 d . . . H14A H 0.6390 0.5548 0.4036 0.147 Uiso 1 1 calc R . . H14B H 0.5264 0.5319 0.3219 0.147 Uiso 1 1 calc R . . H14C H 0.7158 0.4640 0.3417 0.147 Uiso 1 1 calc R . . C15 C 0.3072(6) 0.3833(3) 0.3731(2) 0.0841(10) Uani 1 1 d . . . H15A H 0.3091 0.3104 0.3456 0.126 Uiso 1 1 calc R . . H15B H 0.2673 0.4422 0.3355 0.126 Uiso 1 1 calc R . . H15C H 0.2191 0.3799 0.4172 0.126 Uiso 1 1 calc R . . N1 N 0.5298(3) 0.01741(19) 0.65000(13) 0.0580(6) Uani 1 1 d . . . N2 N 0.4927(5) 0.4087(2) 0.40368(17) 0.0841(8) Uani 1 1 d . . . O1 O 0.8363(3) 0.1460(2) 0.65008(14) 0.0817(6) Uani 1 1 d . . . H1 H 0.7714 0.0897 0.6617 0.123 Uiso 1 1 calc R . . S1 S 0.22380(10) 0.05124(5) 0.56217(4) 0.0558(3) Uani 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 C1 0.0643(17) 0.0524(13) 0.0455(12) 0.0006(10) 0.0011(11) 0.0016(11) C2 0.081(2) 0.0610(15) 0.0607(16) 0.0040(13) 0.0013(14) -0.0184(14) C3 0.092(3) 0.0670(17) 0.0660(17) 0.0050(14) 0.0017(17) -0.0173(16) C4 0.101(3) 0.0611(16) 0.0572(16) 0.0128(13) 0.0067(17) 0.0051(16) C5 0.074(2) 0.0672(16) 0.0521(14) 0.0040(12) -0.0009(13) 0.0157(14) C6 0.0642(17) 0.0522(13) 0.0450(13) -0.0039(10) 0.0048(11) 0.0099(11) C7 0.0518(15) 0.0521(12) 0.0448(12) -0.0065(10) 0.0062(10) 0.0048(10) C8 0.0554(16) 0.0521(13) 0.0440(12) -0.0070(10) 0.0070(11) 0.0022(11) C9 0.0595(18) 0.0705(17) 0.0582(15) -0.0071(13) 0.0111(13) -0.0060(13) C10 0.063(2) 0.087(2) 0.0761(19) -0.0049(16) 0.0062(15) -0.0180(16) C11 0.083(2) 0.0677(17) 0.0724(19) -0.0075(15) 0.0192(17) -0.0185(16) C12 0.079(2) 0.0543(14) 0.0528(14) -0.0050(11) 0.0120(13) -0.0071(13) C13 0.0659(18) 0.0557(14) 0.0492(13) -0.0029(11) 0.0012(12) -0.0014(12) C14 0.145(4) 0.071(2) 0.079(2) 0.0135(17) 0.023(2) -0.024(2) C15 0.108(3) 0.073(2) 0.0706(19) 0.0155(15) -0.0024(19) 0.0024(18) N1 0.0575(14) 0.0663(13) 0.0503(12) 0.0033(10) 0.0040(10) 0.0063(10) N2 0.104(2) 0.0697(16) 0.0779(17) 0.0191(13) -0.0041(16) -0.0200(15) O1 0.0578(14) 0.1099(18) 0.0769(14) 0.0109(12) -0.0101(11) -0.0075(12) S1 0.0606(5) 0.0562(4) 0.0505(4) 0.0058(3) -0.0040(3) -0.0036(3) _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 C1 C6 1.376(4) . ? C1 C2 1.397(4) . ? C1 S1 1.737(3) . ? C2 C3 1.395(4) . ? C2 H2 0.9300 . ? C3 C4 1.361(5) . ? C3 H3 0.9300 . ? C4 C5 1.387(5) . ? C4 H4 0.9300 . ? C5 C6 1.384(4) . ? C5 H5 0.9300 . ? C6 N1 1.408(3) . ? C7 N1 1.301(3) . ? C7 C8 1.448(4) . ? C7 S1 1.751(3) . ? C8 C9 1.396(4) . ? C8 C13 1.400(4) . ? C9 O1 1.377(4) . ? C9 C10 1.387(4) . ? C10 C11 1.365(5) . ? C10 H10 0.9300 . ? C11 C12 1.418(5) . ? C11 H11 0.9300 . ? C12 N2 1.385(4) . ? C12 C13 1.388(4) . ? C13 H13 0.9300 . ? C14 N2 1.442(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N2 1.411(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? O1 H1 0.8200 . ? 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 C6 C1 C2 121.1(2) . . ? C6 C1 S1 110.4(2) . . ? C2 C1 S1 128.5(2) . . ? C3 C2 C1 116.7(3) . . ? C3 C2 H2 121.6 . . ? C1 C2 H2 121.6 . . ? C4 C3 C2 121.6(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 121.9(3) . . ? C3 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C6 C5 C4 116.9(3) . . ? C6 C5 H5 121.5 . . ? C4 C5 H5 121.5 . . ? C1 C6 C5 121.8(3) . . ? C1 C6 N1 114.4(2) . . ? C5 C6 N1 123.9(3) . . ? N1 C7 C8 123.4(3) . . ? N1 C7 S1 115.0(2) . . ? C8 C7 S1 121.51(19) . . ? C9 C8 C13 118.9(2) . . ? C9 C8 C7 119.7(2) . . ? C13 C8 C7 121.4(2) . . ? O1 C9 C10 117.7(3) . . ? O1 C9 C8 123.1(3) . . ? C10 C9 C8 119.2(3) . . ? C11 C10 C9 121.4(3) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 121.1(3) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? N2 C12 C13 121.8(3) . . ? N2 C12 C11 121.4(3) . . ? C13 C12 C11 116.8(3) . . ? C12 C13 C8 122.5(3) . . ? C12 C13 H13 118.8 . . ? C8 C13 H13 118.8 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 N1 C6 111.1(2) . . ? C12 N2 C15 120.5(3) . . ? C12 N2 C14 120.2(3) . . ? C15 N2 C14 118.8(3) . . ? C9 O1 H1 109.5 . . ? C1 S1 C7 89.07(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.949 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.066 #===end data_mPhOH _database_code_depnum_ccdc_archive 'CCDC 805259' #TrackingRef 'crystal data combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H18 N2 O S' _chemical_formula_weight 394.47 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 8.8320(6) _cell_length_b 9.9071(7) _cell_length_c 11.6033(8) _cell_angle_alpha 84.8300(10) _cell_angle_beta 84.4180(10) _cell_angle_gamma 79.0620(10) _cell_volume 989.44(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4924 _cell_measurement_theta_min 1.77 _cell_measurement_theta_max 28.39 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_T_max 0.9683 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 7414 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 28.39 _reflns_number_total 4924 _reflns_number_gt 2675 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0532P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4924 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1083 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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 C1 C 1.1950(3) 0.3235(2) -0.01338(19) 0.0539(5) Uani 1 1 d . . . C2 C 1.3186(3) 0.3891(2) -0.0518(2) 0.0700(7) Uani 1 1 d . . . H2 H 1.4088 0.3718 -0.0135 0.084 Uiso 1 1 calc R . . C3 C 1.3029(3) 0.4809(3) -0.1488(2) 0.0788(8) Uani 1 1 d . . . H3 H 1.3837 0.5263 -0.1763 0.095 Uiso 1 1 calc R . . C4 C 1.1690(3) 0.5061(2) -0.2054(2) 0.0739(7) Uani 1 1 d . . . H4 H 1.1617 0.5680 -0.2707 0.089 Uiso 1 1 calc R . . C5 C 1.0467(3) 0.4424(2) -0.16831(19) 0.0626(6) Uani 1 1 d . . . H5 H 0.9572 0.4605 -0.2075 0.075 Uiso 1 1 calc R . . C6 C 1.0593(3) 0.3497(2) -0.07021(17) 0.0492(5) Uani 1 1 d . . . C7 C 0.9934(2) 0.19604(19) 0.06785(16) 0.0451(5) Uani 1 1 d . . . C8 C 0.9002(2) 0.10363(19) 0.13302(16) 0.0439(5) Uani 1 1 d . . . C9 C 0.7559(2) 0.0924(2) 0.09798(17) 0.0494(5) Uani 1 1 d . . . C10 C 0.6769(2) -0.0049(2) 0.15469(18) 0.0550(6) Uani 1 1 d . . . H10 H 0.5813 -0.0126 0.1313 0.066 Uiso 1 1 calc R . . C11 C 0.7376(2) -0.0907(2) 0.24556(17) 0.0515(5) Uani 1 1 d . . . H11 H 0.6842 -0.1579 0.2808 0.062 Uiso 1 1 calc R . . C12 C 0.8774(2) -0.0784(2) 0.28524(16) 0.0450(5) Uani 1 1 d . . . C13 C 0.9552(2) 0.0201(2) 0.22998(16) 0.0454(5) Uani 1 1 d . . . H13 H 1.0468 0.0318 0.2577 0.055 Uiso 1 1 calc R . . C14 C 0.8298(2) -0.2006(2) 0.47432(16) 0.0421(5) Uani 1 1 d . . . C15 C 0.7278(3) -0.0994(2) 0.52865(18) 0.0557(6) Uani 1 1 d . . . H15 H 0.7260 -0.0075 0.5031 0.067 Uiso 1 1 calc R . . C16 C 0.6280(3) -0.1328(3) 0.6208(2) 0.0713(7) Uani 1 1 d . . . H16 H 0.5577 -0.0636 0.6563 0.086 Uiso 1 1 calc R . . C17 C 0.6320(3) -0.2676(4) 0.6603(2) 0.0768(8) Uani 1 1 d . . . H17 H 0.5666 -0.2898 0.7240 0.092 Uiso 1 1 calc R . . C18 C 0.7322(3) -0.3699(3) 0.6059(2) 0.0716(8) Uani 1 1 d . . . H18 H 0.7342 -0.4616 0.6324 0.086 Uiso 1 1 calc R . . C19 C 0.8298(3) -0.3372(2) 0.5121(2) 0.0557(6) Uani 1 1 d . . . H19 H 0.8959 -0.4070 0.4741 0.067 Uiso 1 1 calc R . . C20 C 1.0964(2) -0.21248(18) 0.38913(17) 0.0425(5) Uani 1 1 d . . . C21 C 1.1541(2) -0.2431(2) 0.49775(18) 0.0523(5) Uani 1 1 d . . . H21 H 1.0873 -0.2332 0.5648 0.063 Uiso 1 1 calc R . . C22 C 1.3106(3) -0.2884(2) 0.5058(2) 0.0661(7) Uani 1 1 d . . . H22 H 1.3477 -0.3114 0.5787 0.079 Uiso 1 1 calc R . . C23 C 1.4124(3) -0.3001(2) 0.4091(2) 0.0688(7) Uani 1 1 d . . . H23 H 1.5179 -0.3287 0.4159 0.083 Uiso 1 1 calc R . . C24 C 1.3558(2) -0.2688(2) 0.3017(2) 0.0590(6) Uani 1 1 d . . . H24 H 1.4238 -0.2758 0.2352 0.071 Uiso 1 1 calc R . . C25 C 1.1995(2) -0.2273(2) 0.29157(18) 0.0500(5) Uani 1 1 d . . . H25 H 1.1629 -0.2091 0.2182 0.060 Uiso 1 1 calc R . . N1 N 0.9460(2) 0.27621(17) -0.02239(14) 0.0499(4) Uani 1 1 d . . . N2 N 0.93599(18) -0.16709(17) 0.38042(14) 0.0519(5) Uani 1 1 d . . . O1 O 0.69061(18) 0.17319(18) 0.00813(13) 0.0699(5) Uani 1 1 d . . . H1 H 0.7481 0.2260 -0.0193 0.105 Uiso 1 1 calc R . . S1 S 1.17908(7) 0.20323(6) 0.10280(5) 0.05785(19) Uani 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 C1 0.0621(14) 0.0429(12) 0.0522(13) -0.0002(10) -0.0012(11) -0.0019(10) C2 0.0635(16) 0.0624(15) 0.0804(18) 0.0014(13) 0.0023(13) -0.0091(13) C3 0.085(2) 0.0602(16) 0.085(2) 0.0070(14) 0.0188(16) -0.0167(14) C4 0.101(2) 0.0523(15) 0.0600(16) 0.0102(12) 0.0113(15) -0.0080(15) C5 0.0839(18) 0.0509(13) 0.0479(13) 0.0067(11) -0.0024(12) -0.0058(12) C6 0.0634(14) 0.0403(11) 0.0391(11) -0.0006(9) 0.0008(10) -0.0010(10) C7 0.0541(12) 0.0427(11) 0.0350(11) -0.0010(9) -0.0056(9) 0.0001(10) C8 0.0496(12) 0.0432(11) 0.0348(11) 0.0012(9) -0.0045(9) 0.0002(9) C9 0.0478(12) 0.0573(13) 0.0373(11) 0.0048(10) -0.0052(9) 0.0018(10) C10 0.0438(12) 0.0720(15) 0.0462(12) 0.0028(11) -0.0080(10) -0.0037(11) C11 0.0474(12) 0.0575(13) 0.0458(12) 0.0027(10) -0.0002(10) -0.0052(10) C12 0.0452(12) 0.0471(12) 0.0370(11) 0.0055(9) -0.0033(9) 0.0022(9) C13 0.0457(12) 0.0495(12) 0.0383(11) 0.0039(9) -0.0086(9) -0.0024(9) C14 0.0412(11) 0.0441(11) 0.0390(11) 0.0071(9) -0.0051(9) -0.0065(9) C15 0.0615(14) 0.0513(13) 0.0526(14) -0.0013(11) 0.0014(11) -0.0103(11) C16 0.0612(15) 0.098(2) 0.0537(15) -0.0142(14) 0.0066(12) -0.0127(14) C17 0.0645(17) 0.131(3) 0.0439(14) 0.0191(16) -0.0102(12) -0.0505(18) C18 0.0786(18) 0.0738(18) 0.0723(18) 0.0341(15) -0.0330(15) -0.0434(16) C19 0.0593(14) 0.0432(12) 0.0634(14) 0.0099(11) -0.0168(11) -0.0069(10) C20 0.0442(11) 0.0381(11) 0.0433(11) 0.0083(9) -0.0065(9) -0.0068(9) C21 0.0542(13) 0.0575(13) 0.0460(12) 0.0133(10) -0.0087(10) -0.0179(11) C22 0.0614(15) 0.0751(16) 0.0680(16) 0.0295(13) -0.0300(13) -0.0320(13) C23 0.0426(13) 0.0722(16) 0.0900(19) 0.0288(14) -0.0160(13) -0.0170(12) C24 0.0454(13) 0.0590(14) 0.0678(15) 0.0086(12) 0.0008(11) -0.0064(11) C25 0.0491(13) 0.0522(12) 0.0456(12) 0.0048(10) -0.0054(10) -0.0046(10) N1 0.0604(11) 0.0474(10) 0.0382(9) 0.0042(8) -0.0083(8) -0.0016(9) N2 0.0425(10) 0.0600(11) 0.0440(10) 0.0181(8) -0.0009(8) 0.0023(8) O1 0.0627(10) 0.0871(12) 0.0547(10) 0.0254(9) -0.0224(8) -0.0061(9) S1 0.0576(4) 0.0567(4) 0.0563(4) 0.0116(3) -0.0132(3) -0.0061(3) _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 C1 C2 1.391(3) . ? C1 C6 1.394(3) . ? C1 S1 1.730(2) . ? C2 C3 1.383(3) . ? C2 H2 0.9300 . ? C3 C4 1.379(3) . ? C3 H3 0.9300 . ? C4 C5 1.367(3) . ? C4 H4 0.9300 . ? C5 C6 1.396(3) . ? C5 H5 0.9300 . ? C6 N1 1.391(3) . ? C7 N1 1.308(2) . ? C7 C8 1.458(3) . ? C7 S1 1.743(2) . ? C8 C9 1.401(3) . ? C8 C13 1.404(2) . ? C9 O1 1.361(2) . ? C9 C10 1.379(3) . ? C10 C11 1.378(3) . ? C10 H10 0.9300 . ? C11 C12 1.389(3) . ? C11 H11 0.9300 . ? C12 C13 1.376(3) . ? C12 N2 1.423(2) . ? C13 H13 0.9300 . ? C14 C15 1.369(3) . ? C14 C19 1.384(3) . ? C14 N2 1.426(2) . ? C15 C16 1.376(3) . ? C15 H15 0.9300 . ? C16 C17 1.367(4) . ? C16 H16 0.9300 . ? C17 C18 1.369(4) . ? C17 H17 0.9300 . ? C18 C19 1.376(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C25 1.383(3) . ? C20 C21 1.392(3) . ? C20 N2 1.413(2) . ? C21 C22 1.379(3) . ? C21 H21 0.9300 . ? C22 C23 1.366(3) . ? C22 H22 0.9300 . ? C23 C24 1.376(3) . ? C23 H23 0.9300 . ? C24 C25 1.376(3) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? O1 H1 0.8200 . ? 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 C2 C1 C6 121.3(2) . . ? C2 C1 S1 129.07(19) . . ? C6 C1 S1 109.65(16) . . ? C3 C2 C1 117.8(2) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C4 C3 C2 120.9(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 121.8(2) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 118.4(2) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? N1 C6 C1 114.90(17) . . ? N1 C6 C5 125.3(2) . . ? C1 C6 C5 119.8(2) . . ? N1 C7 C8 122.77(18) . . ? N1 C7 S1 115.28(15) . . ? C8 C7 S1 121.92(13) . . ? C9 C8 C13 118.33(18) . . ? C9 C8 C7 120.78(16) . . ? C13 C8 C7 120.85(17) . . ? O1 C9 C10 118.07(18) . . ? O1 C9 C8 122.41(18) . . ? C10 C9 C8 119.51(17) . . ? C11 C10 C9 120.9(2) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 120.9(2) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 118.25(17) . . ? C13 C12 N2 122.08(17) . . ? C11 C12 N2 119.67(18) . . ? C12 C13 C8 121.93(18) . . ? C12 C13 H13 119.0 . . ? C8 C13 H13 119.0 . . ? C15 C14 C19 119.22(19) . . ? C15 C14 N2 120.94(17) . . ? C19 C14 N2 119.84(19) . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.0(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 120.1(2) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C14 120.1(2) . . ? C18 C19 H19 120.0 . . ? C14 C19 H19 120.0 . . ? C25 C20 C21 118.35(18) . . ? C25 C20 N2 121.57(17) . . ? C21 C20 N2 120.08(18) . . ? C22 C21 C20 119.9(2) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C23 C22 C21 121.5(2) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C22 C23 C24 118.7(2) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C23 C24 C25 120.7(2) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C20 120.80(19) . . ? C24 C25 H25 119.6 . . ? C20 C25 H25 119.6 . . ? C7 N1 C6 110.80(17) . . ? C20 N2 C12 121.97(16) . . ? C20 N2 C14 119.27(14) . . ? C12 N2 C14 118.51(15) . . ? C9 O1 H1 109.5 . . ? C1 S1 C7 89.37(10) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.167 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.044 #===end data_pCzOH _database_code_depnum_ccdc_archive 'CCDC 805260' #TrackingRef 'crystal data combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 N2 O S' _chemical_formula_weight 392.46 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.949(2) _cell_length_b 15.759(3) _cell_length_c 13.031(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.10(3) _cell_angle_gamma 90.00 _cell_volume 1930.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4382 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 27.48 _exptl_crystal_description colorless _exptl_crystal_colour block _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9416 _exptl_absorpt_correction_T_max 0.9592 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Omega scan' _diffrn_measurement_method 10.0 _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 18395 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4382 _reflns_number_gt 3214 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0541P)^2^+0.3109P] 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 4382 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 C1 C 0.45031(17) 0.02839(11) 1.22899(13) 0.0465(4) Uani 1 1 d . . . C2 C 0.4915(2) -0.03933(12) 1.30052(16) 0.0627(5) Uani 1 1 d . . . H2 H 0.5697 -0.0726 1.3030 0.075 Uiso 1 1 calc R . . C3 C 0.4130(2) -0.05558(14) 1.36749(18) 0.0752(6) Uani 1 1 d . . . H3 H 0.4389 -0.1004 1.4165 0.090 Uiso 1 1 calc R . . C4 C 0.2962(2) -0.00641(16) 1.36330(18) 0.0767(6) Uani 1 1 d . . . H4 H 0.2437 -0.0198 1.4085 0.092 Uiso 1 1 calc R . . C5 C 0.2556(2) 0.06177(13) 1.29402(17) 0.0641(5) Uani 1 1 d . . . H5 H 0.1779 0.0950 1.2928 0.077 Uiso 1 1 calc R . . C6 C 0.33463(17) 0.07949(10) 1.22571(13) 0.0463(4) Uani 1 1 d . . . C7 C 0.39636(15) 0.14218(10) 1.09498(13) 0.0408(3) Uani 1 1 d . . . C8 C 0.39153(15) 0.20204(10) 1.00881(12) 0.0400(3) Uani 1 1 d . . . C9 C 0.28932(16) 0.26740(10) 0.98185(13) 0.0431(4) Uani 1 1 d . . . C10 C 0.28448(16) 0.32393(10) 0.89932(13) 0.0445(4) Uani 1 1 d . . . H10 H 0.2168 0.3670 0.8818 0.053 Uiso 1 1 calc R . . C11 C 0.37984(16) 0.31651(10) 0.84301(13) 0.0430(4) Uani 1 1 d . . . C12 C 0.48055(17) 0.25176(11) 0.86757(14) 0.0474(4) Uani 1 1 d . . . H12 H 0.5440 0.2466 0.8291 0.057 Uiso 1 1 calc R . . C13 C 0.48520(16) 0.19561(10) 0.94921(13) 0.0451(4) Uani 1 1 d . . . H13 H 0.5523 0.1522 0.9653 0.054 Uiso 1 1 calc R . . C14 C 0.37857(15) 0.46443(10) 0.77210(14) 0.0446(4) Uani 1 1 d . . . C15 C 0.38852(18) 0.51245(11) 0.86303(15) 0.0525(4) Uani 1 1 d . . . H15 H 0.3894 0.4870 0.9277 0.063 Uiso 1 1 calc R . . C16 C 0.3971(2) 0.59970(12) 0.85458(18) 0.0637(5) Uani 1 1 d . . . H16 H 0.4046 0.6336 0.9147 0.076 Uiso 1 1 calc R . . C17 C 0.3946(2) 0.63744(13) 0.75749(19) 0.0680(6) Uani 1 1 d . . . H17 H 0.4007 0.6962 0.7537 0.082 Uiso 1 1 calc R . . C18 C 0.38324(19) 0.58957(12) 0.66746(17) 0.0603(5) Uani 1 1 d . . . H18 H 0.3811 0.6156 0.6029 0.072 Uiso 1 1 calc R . . C19 C 0.37490(16) 0.50138(11) 0.67338(14) 0.0481(4) Uani 1 1 d . . . C20 C 0.36679(16) 0.43315(11) 0.59804(14) 0.0488(4) Uani 1 1 d . . . C21 C 0.35437(19) 0.42952(15) 0.48790(16) 0.0616(5) Uani 1 1 d . . . H21 H 0.3516 0.4791 0.4486 0.074 Uiso 1 1 calc R . . C22 C 0.3464(2) 0.35192(17) 0.43879(16) 0.0688(6) Uani 1 1 d . . . H22 H 0.3379 0.3493 0.3656 0.083 Uiso 1 1 calc R . . C23 C 0.35092(19) 0.27729(15) 0.49617(16) 0.0650(5) Uani 1 1 d . . . H23 H 0.3471 0.2256 0.4610 0.078 Uiso 1 1 calc R . . C24 C 0.36101(18) 0.27804(12) 0.60457(15) 0.0557(4) Uani 1 1 d . . . H24 H 0.3624 0.2279 0.6426 0.067 Uiso 1 1 calc R . . C25 C 0.36891(16) 0.35667(11) 0.65427(13) 0.0462(4) Uani 1 1 d . . . N1 N 0.30661(14) 0.14380(9) 1.14887(11) 0.0478(3) Uani 1 1 d . . . N2 N 0.37588(14) 0.37596(9) 0.76040(11) 0.0457(3) Uani 1 1 d . . . O1 O 0.19176(14) 0.27698(8) 1.03195(11) 0.0613(4) Uani 1 1 d . . . H1 H 0.2027 0.2399 1.0781 0.092 Uiso 1 1 calc R . . S1 S 0.52411(5) 0.06191(3) 1.13278(4) 0.05150(15) Uani 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 C1 0.0473(8) 0.0457(9) 0.0455(9) 0.0050(7) 0.0141(7) -0.0072(7) C2 0.0625(11) 0.0557(11) 0.0691(13) 0.0208(10) 0.0204(10) 0.0019(9) C3 0.0776(14) 0.0738(14) 0.0718(14) 0.0322(11) 0.0209(11) -0.0070(11) C4 0.0772(14) 0.0946(17) 0.0681(14) 0.0233(12) 0.0374(11) -0.0108(13) C5 0.0615(11) 0.0758(13) 0.0637(12) 0.0112(10) 0.0322(10) -0.0001(10) C6 0.0480(9) 0.0475(9) 0.0435(9) 0.0034(7) 0.0154(7) -0.0066(7) C7 0.0395(7) 0.0389(8) 0.0442(9) 0.0003(7) 0.0137(6) -0.0022(6) C8 0.0409(7) 0.0360(8) 0.0435(9) 0.0032(6) 0.0141(6) -0.0015(6) C9 0.0440(8) 0.0398(8) 0.0479(9) -0.0001(7) 0.0186(7) 0.0004(7) C10 0.0442(8) 0.0371(8) 0.0515(10) 0.0053(7) 0.0145(7) 0.0047(7) C11 0.0428(8) 0.0395(8) 0.0445(9) 0.0070(7) 0.0112(7) -0.0027(7) C12 0.0441(8) 0.0501(9) 0.0518(10) 0.0109(8) 0.0209(7) 0.0041(7) C13 0.0411(8) 0.0440(9) 0.0517(10) 0.0099(7) 0.0174(7) 0.0065(7) C14 0.0366(7) 0.0420(9) 0.0515(10) 0.0095(7) 0.0094(7) -0.0005(7) C15 0.0515(9) 0.0471(10) 0.0547(11) 0.0057(8) 0.0116(8) -0.0009(8) C16 0.0591(11) 0.0479(11) 0.0772(14) -0.0015(10) 0.0129(10) -0.0008(9) C17 0.0652(12) 0.0414(10) 0.0911(16) 0.0142(10) 0.0169(11) 0.0006(9) C18 0.0515(10) 0.0539(11) 0.0727(13) 0.0261(10) 0.0162(9) 0.0025(8) C19 0.0363(8) 0.0493(9) 0.0554(10) 0.0162(8) 0.0106(7) 0.0005(7) C20 0.0352(8) 0.0607(11) 0.0499(10) 0.0146(8) 0.0131(7) 0.0013(7) C21 0.0470(9) 0.0855(15) 0.0524(11) 0.0184(10) 0.0162(8) -0.0031(9) C22 0.0507(10) 0.1100(19) 0.0478(11) 0.0018(12) 0.0191(8) -0.0047(11) C23 0.0504(10) 0.0852(15) 0.0596(12) -0.0116(11) 0.0183(9) 0.0016(10) C24 0.0509(9) 0.0584(11) 0.0570(11) 0.0014(9) 0.0169(8) 0.0041(8) C25 0.0388(8) 0.0534(10) 0.0455(9) 0.0078(8) 0.0127(7) 0.0016(7) N1 0.0498(8) 0.0479(8) 0.0496(8) 0.0059(6) 0.0216(6) 0.0012(6) N2 0.0508(7) 0.0406(7) 0.0446(8) 0.0098(6) 0.0140(6) 0.0004(6) O1 0.0682(8) 0.0565(8) 0.0746(9) 0.0159(6) 0.0444(7) 0.0207(6) S1 0.0495(2) 0.0512(3) 0.0586(3) 0.0160(2) 0.0243(2) 0.01029(19) _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 C1 C2 1.388(2) . ? C1 C6 1.394(2) . ? C1 S1 1.7299(17) . ? C2 C3 1.372(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(3) . ? C3 H3 0.9300 . ? C4 C5 1.376(3) . ? C4 H4 0.9300 . ? C5 C6 1.395(2) . ? C5 H5 0.9300 . ? C6 N1 1.387(2) . ? C7 N1 1.3045(19) . ? C7 C8 1.455(2) . ? C7 S1 1.7459(16) . ? C8 C13 1.398(2) . ? C8 C9 1.409(2) . ? C9 O1 1.3438(18) . ? C9 C10 1.385(2) . ? C10 C11 1.381(2) . ? C10 H10 0.9300 . ? C11 C12 1.392(2) . ? C11 N2 1.4177(19) . ? C12 C13 1.373(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.382(2) . ? C14 C19 1.402(2) . ? C14 N2 1.402(2) . ? C15 C16 1.384(3) . ? C15 H15 0.9300 . ? C16 C17 1.391(3) . ? C16 H16 0.9300 . ? C17 C18 1.368(3) . ? C17 H17 0.9300 . ? C18 C19 1.396(3) . ? C18 H18 0.9300 . ? C19 C20 1.440(3) . ? C20 C21 1.401(3) . ? C20 C25 1.407(2) . ? C21 C22 1.370(3) . ? C21 H21 0.9300 . ? C22 C23 1.387(3) . ? C22 H22 0.9300 . ? C23 C24 1.383(3) . ? C23 H23 0.9300 . ? C24 C25 1.388(3) . ? C24 H24 0.9300 . ? C25 N2 1.395(2) . ? O1 H1 0.8200 . ? 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 C2 C1 C6 121.63(16) . . ? C2 C1 S1 128.28(14) . . ? C6 C1 S1 110.09(12) . . ? C3 C2 C1 117.79(19) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 121.07(19) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 121.70(19) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 117.98(19) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? N1 C6 C1 114.40(14) . . ? N1 C6 C5 125.77(16) . . ? C1 C6 C5 119.80(16) . . ? N1 C7 C8 123.17(14) . . ? N1 C7 S1 115.19(12) . . ? C8 C7 S1 121.64(11) . . ? C13 C8 C9 118.18(14) . . ? C13 C8 C7 121.45(14) . . ? C9 C8 C7 120.35(14) . . ? O1 C9 C10 117.24(14) . . ? O1 C9 C8 122.56(14) . . ? C10 C9 C8 120.18(14) . . ? C11 C10 C9 120.17(14) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.52(14) . . ? C10 C11 N2 119.61(14) . . ? C12 C11 N2 119.87(14) . . ? C13 C12 C11 119.33(15) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C8 121.61(15) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? C15 C14 C19 122.17(16) . . ? C15 C14 N2 129.15(15) . . ? C19 C14 N2 108.64(15) . . ? C14 C15 C16 117.70(17) . . ? C14 C15 H15 121.1 . . ? C16 C15 H15 121.1 . . ? C15 C16 C17 120.9(2) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C18 C17 C16 121.08(18) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 119.42(18) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C18 C19 C14 118.70(18) . . ? C18 C19 C20 134.16(17) . . ? C14 C19 C20 107.11(15) . . ? C21 C20 C25 118.67(18) . . ? C21 C20 C19 134.05(17) . . ? C25 C20 C19 107.25(15) . . ? C22 C21 C20 119.15(19) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 121.22(19) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 121.5(2) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C23 C24 C25 117.26(18) . . ? C23 C24 H24 121.4 . . ? C25 C24 H24 121.4 . . ? C24 C25 N2 129.31(16) . . ? C24 C25 C20 122.19(17) . . ? N2 C25 C20 108.48(15) . . ? C7 N1 C6 111.28(14) . . ? C25 N2 C14 108.50(13) . . ? C25 N2 C11 126.06(14) . . ? C14 N2 C11 125.44(14) . . ? C9 O1 H1 109.5 . . ? C1 S1 C7 89.04(8) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.384 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.038 #===end data_pPhOH _database_code_depnum_ccdc_archive 'CCDC 805261' #TrackingRef 'crystal data combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H18 N2 O S' _chemical_formula_weight 394.47 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 P2(1)/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 20.542(4) _cell_length_b 7.2295(14) _cell_length_c 13.494(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.92(3) _cell_angle_gamma 90.00 _cell_volume 1979.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4505 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9351 _exptl_absorpt_correction_T_max 0.9684 _exptl_absorpt_process_details ? _exptl_special_details ; Higash,T(1995) Progrom for Absorption Correcttion. Rigaku Corporation,Tokyo,Japan. ; _diffrn_ambient_temperature 293(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 'Omega scan' _diffrn_measurement_method 10.0 _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 18151 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4505 _reflns_number_gt 2657 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-97 (Sheldrick, 1990)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0651P)^2^+0.1444P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4505 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1105 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 C1 C 0.43841(12) 0.8793(3) 0.61744(17) 0.0500(6) Uani 1 1 d . . . C2 C 0.37030(13) 0.8863(4) 0.6200(2) 0.0650(7) Uani 1 1 d . . . H2 H 0.3442 0.7808 0.6099 0.078 Uiso 1 1 calc R . . C3 C 0.34372(14) 1.0553(4) 0.6380(2) 0.0691(8) Uani 1 1 d . . . H3 H 0.2987 1.0633 0.6399 0.083 Uiso 1 1 calc R . . C4 C 0.38128(14) 1.2126(4) 0.65333(19) 0.0639(7) Uani 1 1 d . . . H4 H 0.3613 1.3244 0.6644 0.077 Uiso 1 1 calc R . . C5 C 0.44734(13) 1.2072(3) 0.65256(17) 0.0545(6) Uani 1 1 d . . . H5 H 0.4725 1.3142 0.6637 0.065 Uiso 1 1 calc R . . C6 C 0.47671(11) 1.0401(3) 0.63488(15) 0.0440(5) Uani 1 1 d . . . C7 C 0.55610(11) 0.8386(3) 0.61260(16) 0.0427(5) Uani 1 1 d . . . C8 C 0.62172(11) 0.7722(3) 0.60612(16) 0.0420(5) Uani 1 1 d . . . C9 C 0.67554(11) 0.8939(3) 0.61547(17) 0.0462(5) Uani 1 1 d . . . C10 C 0.73790(12) 0.8326(3) 0.60601(18) 0.0522(6) Uani 1 1 d . . . H10 H 0.7724 0.9170 0.6098 0.063 Uiso 1 1 calc R . . C11 C 0.74981(11) 0.6466(3) 0.59086(18) 0.0495(6) Uani 1 1 d . . . C12 C 0.69718(12) 0.5217(3) 0.58535(18) 0.0516(6) Uani 1 1 d . . . H12 H 0.7044 0.3961 0.5771 0.062 Uiso 1 1 calc R . . C13 C 0.63556(11) 0.5845(3) 0.59211(17) 0.0479(6) Uani 1 1 d . . . H13 H 0.6012 0.4997 0.5873 0.057 Uiso 1 1 calc R . . C14 C 0.87182(12) 0.6732(3) 0.6195(2) 0.0564(6) Uani 1 1 d . . . C15 C 0.87855(14) 0.7640(4) 0.7110(2) 0.0692(8) Uani 1 1 d . . . H15 H 0.8441 0.7616 0.7484 0.083 Uiso 1 1 calc R . . C16 C 0.93549(16) 0.8576(4) 0.7471(3) 0.0893(10) Uani 1 1 d . . . H16 H 0.9390 0.9196 0.8081 0.107 Uiso 1 1 calc R . . C17 C 0.98719(17) 0.8605(5) 0.6941(4) 0.1024(13) Uani 1 1 d . . . H17 H 1.0255 0.9252 0.7183 0.123 Uiso 1 1 calc R . . C18 C 0.98192(15) 0.7677(5) 0.6055(3) 0.0924(11) Uani 1 1 d . . . H18 H 1.0174 0.7666 0.5703 0.111 Uiso 1 1 calc R . . C19 C 0.92457(13) 0.6748(4) 0.5669(2) 0.0714(8) Uani 1 1 d . . . H19 H 0.9215 0.6136 0.5057 0.086 Uiso 1 1 calc R . . C20 C 0.81652(11) 0.4338(3) 0.5095(2) 0.0539(6) Uani 1 1 d . . . C21 C 0.85041(13) 0.2729(3) 0.5382(2) 0.0708(8) Uani 1 1 d . . . H21 H 0.8704 0.2562 0.6043 0.085 Uiso 1 1 calc R . . C22 C 0.85439(16) 0.1354(4) 0.4667(4) 0.0903(11) Uani 1 1 d . . . H22 H 0.8770 0.0264 0.4853 0.108 Uiso 1 1 calc R . . C23 C 0.82525(18) 0.1600(5) 0.3695(3) 0.0919(11) Uani 1 1 d . . . H23 H 0.8283 0.0678 0.3224 0.110 Uiso 1 1 calc R . . C24 C 0.79214(16) 0.3170(5) 0.3418(3) 0.0859(10) Uani 1 1 d . . . H24 H 0.7723 0.3324 0.2755 0.103 Uiso 1 1 calc R . . C25 C 0.78745(13) 0.4552(4) 0.4107(2) 0.0663(7) Uani 1 1 d . . . H25 H 0.7646 0.5634 0.3906 0.080 Uiso 1 1 calc R . . N1 N 0.54359(9) 1.0133(2) 0.63219(13) 0.0455(5) Uani 1 1 d . . . N2 N 0.81269(9) 0.5793(3) 0.58046(17) 0.0581(6) Uani 1 1 d . . . O1 O 0.66834(8) 1.0774(2) 0.63253(15) 0.0640(5) Uani 1 1 d . . . H1 H 0.6296 1.0996 0.6362 0.096 Uiso 1 1 calc R . . S1 S 0.48685(3) 0.69469(8) 0.59465(5) 0.0540(2) Uani 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 C1 0.0549(14) 0.0569(14) 0.0377(14) -0.0016(10) 0.0055(11) -0.0059(11) C2 0.0565(16) 0.0790(18) 0.0585(18) -0.0054(13) 0.0061(13) -0.0142(14) C3 0.0518(15) 0.099(2) 0.0574(18) -0.0024(15) 0.0098(13) 0.0068(16) C4 0.0654(18) 0.0781(18) 0.0471(16) -0.0018(13) 0.0049(13) 0.0160(15) C5 0.0678(17) 0.0564(14) 0.0392(14) 0.0005(11) 0.0075(12) 0.0075(12) C6 0.0490(13) 0.0531(14) 0.0290(12) 0.0026(9) 0.0034(10) -0.0032(11) C7 0.0556(14) 0.0403(12) 0.0325(12) -0.0003(9) 0.0079(10) -0.0045(10) C8 0.0514(13) 0.0375(11) 0.0373(12) -0.0001(9) 0.0073(10) -0.0065(10) C9 0.0548(14) 0.0365(11) 0.0468(14) -0.0020(10) 0.0065(11) -0.0059(10) C10 0.0510(14) 0.0421(13) 0.0634(17) -0.0021(10) 0.0082(12) -0.0119(10) C11 0.0488(13) 0.0447(13) 0.0544(16) 0.0004(10) 0.0063(11) -0.0056(11) C12 0.0564(15) 0.0403(12) 0.0586(16) -0.0027(10) 0.0106(12) -0.0058(11) C13 0.0525(14) 0.0423(13) 0.0494(15) -0.0039(10) 0.0095(11) -0.0109(11) C14 0.0500(14) 0.0476(14) 0.0698(18) 0.0060(12) 0.0035(13) -0.0021(11) C15 0.0641(17) 0.0642(17) 0.075(2) 0.0018(14) -0.0015(15) -0.0071(14) C16 0.076(2) 0.081(2) 0.102(3) -0.0111(18) -0.0153(19) -0.0127(17) C17 0.064(2) 0.082(2) 0.150(4) -0.004(2) -0.017(2) -0.0170(18) C18 0.0509(18) 0.085(2) 0.142(4) 0.010(2) 0.017(2) -0.0096(16) C19 0.0551(16) 0.0655(17) 0.094(2) 0.0060(15) 0.0135(15) -0.0036(13) C20 0.0462(13) 0.0425(13) 0.0745(19) -0.0003(12) 0.0144(13) -0.0014(11) C21 0.0647(17) 0.0537(16) 0.096(2) 0.0138(15) 0.0172(16) 0.0077(13) C22 0.075(2) 0.0457(16) 0.159(4) 0.007(2) 0.048(2) 0.0078(15) C23 0.078(2) 0.077(2) 0.129(4) -0.033(2) 0.046(2) -0.0118(18) C24 0.075(2) 0.107(3) 0.079(2) -0.0237(19) 0.0227(17) -0.0078(19) C25 0.0594(17) 0.0677(17) 0.072(2) -0.0012(14) 0.0117(15) 0.0060(13) N1 0.0492(11) 0.0529(11) 0.0348(11) 0.0029(8) 0.0074(8) 0.0003(9) N2 0.0474(12) 0.0491(12) 0.0774(16) -0.0089(10) 0.0082(11) -0.0030(9) O1 0.0584(10) 0.0379(9) 0.0962(15) -0.0081(8) 0.0132(11) -0.0094(8) S1 0.0551(4) 0.0507(4) 0.0559(4) -0.0055(3) 0.0076(3) -0.0118(3) _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 C1 C6 1.403(3) . ? C1 C2 1.406(3) . ? C1 S1 1.721(2) . ? C2 C3 1.375(4) . ? C2 H2 0.9300 . ? C3 C4 1.371(4) . ? C3 H3 0.9300 . ? C4 C5 1.359(3) . ? C4 H4 0.9300 . ? C5 C6 1.387(3) . ? C5 H5 0.9300 . ? C6 N1 1.394(3) . ? C7 N1 1.324(3) . ? C7 C8 1.446(3) . ? C7 S1 1.748(2) . ? C8 C9 1.403(3) . ? C8 C13 1.405(3) . ? C9 O1 1.358(2) . ? C9 C10 1.380(3) . ? C10 C11 1.388(3) . ? C10 H10 0.9300 . ? C11 C12 1.402(3) . ? C11 N2 1.408(3) . ? C12 C13 1.361(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C19 1.385(4) . ? C14 C15 1.387(4) . ? C14 N2 1.420(3) . ? C15 C16 1.373(4) . ? C15 H15 0.9300 . ? C16 C17 1.370(5) . ? C16 H16 0.9300 . ? C17 C18 1.360(5) . ? C17 H17 0.9300 . ? C18 C19 1.386(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.380(3) . ? C20 C25 1.383(4) . ? C20 N2 1.432(3) . ? C21 C22 1.397(4) . ? C21 H21 0.9300 . ? C22 C23 1.366(5) . ? C22 H22 0.9300 . ? C23 C24 1.347(5) . ? C23 H23 0.9300 . ? C24 C25 1.379(4) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? O1 H1 0.8200 . ? 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 C6 C1 C2 120.0(2) . . ? C6 C1 S1 110.36(17) . . ? C2 C1 S1 129.6(2) . . ? C3 C2 C1 117.4(2) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C4 C3 C2 122.3(3) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C5 C4 C3 121.0(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 N1 125.6(2) . . ? C5 C6 C1 120.2(2) . . ? N1 C6 C1 114.2(2) . . ? N1 C7 C8 122.70(19) . . ? N1 C7 S1 114.60(16) . . ? C8 C7 S1 122.70(15) . . ? C9 C8 C13 116.4(2) . . ? C9 C8 C7 121.01(18) . . ? C13 C8 C7 122.58(19) . . ? O1 C9 C10 117.15(19) . . ? O1 C9 C8 121.5(2) . . ? C10 C9 C8 121.32(19) . . ? C9 C10 C11 120.8(2) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C12 118.7(2) . . ? C10 C11 N2 122.4(2) . . ? C12 C11 N2 118.9(2) . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 122.7(2) . . ? C12 C13 H13 118.6 . . ? C8 C13 H13 118.6 . . ? C19 C14 C15 118.3(3) . . ? C19 C14 N2 120.4(2) . . ? C15 C14 N2 121.3(2) . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 119.3(3) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 121.1(3) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C14 C19 C18 119.9(3) . . ? C14 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C25 119.2(2) . . ? C21 C20 N2 120.6(3) . . ? C25 C20 N2 120.1(2) . . ? C20 C21 C22 119.2(3) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C23 C22 C21 120.5(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C24 C23 C22 120.3(3) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 120.6(3) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C20 120.3(3) . . ? C24 C25 H25 119.8 . . ? C20 C25 H25 119.8 . . ? C7 N1 C6 111.13(18) . . ? C11 N2 C14 122.89(19) . . ? C11 N2 C20 117.83(19) . . ? C14 N2 C20 117.84(19) . . ? C9 O1 H1 109.5 . . ? C1 S1 C7 89.68(11) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.381 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.042