# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name V.Kumar P.Raghavaiah S.Mobin V.Nair _publ_contact_author_name 'Vipin Nair' _publ_contact_author_email vnair@niper.ac.in data_niper2 _database_code_depnum_ccdc_archive 'CCDC 772207' #TrackingRef 'niper2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Cl N3 O S' _chemical_formula_weight 383.88 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.2935(2) _cell_length_b 12.3730(3) _cell_length_c 20.6291(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1861.62(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7258 _cell_measurement_theta_min 3.3811 _cell_measurement_theta_max 32.6512 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_T_min 0.9129 _exptl_absorpt_correction_T_max 0.9582 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8067 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3272 _reflns_number_gt 3053 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0396P)^2^+0.1561P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(5) _refine_ls_number_reflns 3272 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0643 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.69640(6) 1.00439(4) 0.986280(19) 0.02756(12) Uani 1 1 d . . . Cl2 Cl 0.03415(7) 0.99863(4) 0.83723(2) 0.03541(13) Uani 1 1 d . . . O1 O 0.13314(19) 0.90212(11) 1.10180(6) 0.0329(3) Uani 1 1 d . . . N1 N 0.3852(2) 0.96561(11) 1.05040(6) 0.0211(3) Uani 1 1 d . . . N2 N 0.5902(2) 1.08218(12) 1.10129(7) 0.0205(3) Uani 1 1 d . . . N3 N 0.0828(3) 0.71892(13) 0.77664(8) 0.0345(4) Uani 1 1 d . . . C1 C 0.1904(3) 0.81406(13) 0.88145(8) 0.0199(4) Uani 1 1 d . . . C2 C 0.2915(3) 0.75502(14) 0.92645(8) 0.0230(4) Uani 1 1 d . . . H2 H 0.3154 0.6806 0.9190 0.028 Uiso 1 1 calc R . . C3 C 0.3573(3) 0.80423(14) 0.98187(8) 0.0235(4) Uani 1 1 d . . . H3 H 0.4263 0.7640 1.0126 0.028 Uiso 1 1 calc R . . C4 C 0.3219(2) 0.91228(14) 0.99227(8) 0.0212(4) Uani 1 1 d . . . C5 C 0.2176(3) 0.97178(14) 0.94910(8) 0.0228(4) Uani 1 1 d . . . H5 H 0.1897 1.0453 0.9579 0.027 Uiso 1 1 calc R . . C6 C 0.1547(3) 0.92330(14) 0.89327(8) 0.0219(4) Uani 1 1 d . . . C7 C 0.1285(3) 0.76284(14) 0.82259(9) 0.0243(4) Uani 1 1 d . . . C8 C 0.2730(3) 0.95435(14) 1.10533(8) 0.0231(4) Uani 1 1 d . . . C9 C 0.3406(2) 1.01045(15) 1.16477(7) 0.0246(4) Uani 1 1 d . . . H9A H 0.4240 0.9619 1.1890 0.030 Uiso 1 1 calc R . . H9B H 0.2356 1.0284 1.1932 0.030 Uiso 1 1 calc R . . C10 C 0.4417(3) 1.11316(15) 1.14636(8) 0.0243(4) Uani 1 1 d . . . H10 H 0.4985 1.1440 1.1864 0.029 Uiso 1 1 calc R . . C11 C 0.3135(3) 1.19786(16) 1.11743(10) 0.0327(4) Uani 1 1 d . . . H11A H 0.3848 1.2613 1.1043 0.049 Uiso 1 1 calc R . . H11B H 0.2223 1.2192 1.1499 0.049 Uiso 1 1 calc R . . H11C H 0.2511 1.1675 1.0795 0.049 Uiso 1 1 calc R . . C12 C 0.5556(2) 1.01999(13) 1.04951(8) 0.0207(4) Uani 1 1 d . . . C13 C 0.7757(3) 1.13076(14) 1.11089(8) 0.0223(4) Uani 1 1 d . . . H13 H 0.8646 1.0865 1.0852 0.027 Uiso 1 1 calc R . . C14 C 0.7813(3) 1.24508(16) 1.08370(9) 0.0344(5) Uani 1 1 d . . . H14A H 0.7421 1.2441 1.0383 0.052 Uiso 1 1 calc R . . H14B H 0.9066 1.2733 1.0865 0.052 Uiso 1 1 calc R . . H14C H 0.6987 1.2915 1.1088 0.052 Uiso 1 1 calc R . . C15 C 0.8289(2) 1.11995(13) 1.18168(8) 0.0200(4) Uani 1 1 d . . . C16 C 0.8555(3) 1.20800(15) 1.22240(9) 0.0281(4) Uani 1 1 d . . . H16 H 0.8423 1.2792 1.2058 0.034 Uiso 1 1 calc R . . C17 C 0.9011(3) 1.19304(18) 1.28677(10) 0.0370(5) Uani 1 1 d . . . H17 H 0.9203 1.2541 1.3139 0.044 Uiso 1 1 calc R . . C18 C 0.9189(3) 1.09069(19) 1.31212(10) 0.0360(5) Uani 1 1 d . . . H18 H 0.9485 1.0809 1.3566 0.043 Uiso 1 1 calc R . . C19 C 0.8933(2) 1.00209(19) 1.27218(9) 0.0328(4) Uani 1 1 d . . . H19 H 0.9062 0.9311 1.2892 0.039 Uiso 1 1 calc R . . C20 C 0.8492(2) 1.01653(15) 1.20759(8) 0.0250(4) Uani 1 1 d . . . H20 H 0.8325 0.9552 1.1805 0.030 Uiso 1 1 calc R . . 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 0.0270(2) 0.0371(2) 0.0186(2) -0.0049(2) 0.00512(16) -0.0054(3) Cl2 0.0462(3) 0.0328(2) 0.0273(2) 0.0005(2) -0.01599(19) 0.0103(3) O1 0.0299(8) 0.0420(8) 0.0269(7) -0.0009(6) 0.0049(6) -0.0123(7) N1 0.0218(8) 0.0270(8) 0.0145(7) 0.0004(5) -0.0016(6) -0.0029(6) N2 0.0180(8) 0.0269(7) 0.0165(7) -0.0018(6) -0.0008(6) -0.0003(6) N3 0.0424(11) 0.0314(8) 0.0297(9) -0.0037(8) -0.0083(8) 0.0007(8) C1 0.0199(9) 0.0232(8) 0.0166(8) -0.0009(6) 0.0014(7) -0.0029(8) C2 0.0240(11) 0.0200(9) 0.0249(9) 0.0011(7) 0.0016(8) 0.0016(8) C3 0.0229(10) 0.0270(9) 0.0205(9) 0.0049(7) -0.0030(7) 0.0015(8) C4 0.0186(9) 0.0296(9) 0.0153(8) 0.0004(7) 0.0023(7) -0.0024(8) C5 0.0262(10) 0.0208(9) 0.0212(9) 0.0003(7) -0.0005(7) -0.0010(7) C6 0.0207(9) 0.0271(9) 0.0178(8) 0.0043(7) -0.0018(7) 0.0006(8) C7 0.0246(10) 0.0244(9) 0.0240(9) 0.0008(8) -0.0015(8) 0.0003(8) C8 0.0224(10) 0.0259(9) 0.0210(9) 0.0048(7) 0.0006(7) 0.0015(8) C9 0.0212(9) 0.0356(10) 0.0170(8) -0.0004(8) 0.0015(6) 0.0017(9) C10 0.0186(10) 0.0346(10) 0.0198(9) -0.0061(7) -0.0013(7) 0.0017(8) C11 0.0260(10) 0.0355(11) 0.0367(10) -0.0031(9) 0.0005(9) 0.0059(9) C12 0.0218(9) 0.0231(10) 0.0171(8) 0.0028(7) -0.0034(7) -0.0004(8) C13 0.0184(9) 0.0258(9) 0.0228(9) -0.0015(7) 0.0001(7) -0.0024(7) C14 0.0355(13) 0.0368(11) 0.0309(11) 0.0100(8) -0.0031(9) -0.0096(10) C15 0.0129(9) 0.0260(9) 0.0212(8) -0.0034(7) 0.0019(7) -0.0016(7) C16 0.0231(10) 0.0292(10) 0.0320(10) -0.0056(8) -0.0024(8) -0.0016(8) C17 0.0280(11) 0.0541(13) 0.0289(11) -0.0176(10) -0.0043(9) -0.0070(10) C18 0.0218(11) 0.0650(15) 0.0212(10) 0.0007(10) -0.0023(8) -0.0046(11) C19 0.0217(9) 0.0463(11) 0.0304(9) 0.0130(10) -0.0005(7) 0.0006(11) C20 0.0197(9) 0.0266(10) 0.0286(9) -0.0011(8) 0.0009(7) 0.0002(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 C12 1.6713(17) . ? Cl2 C6 1.7259(17) . ? O1 C8 1.210(2) . ? N1 C8 1.405(2) . ? N1 C12 1.414(2) . ? N1 C4 1.444(2) . ? N2 C12 1.341(2) . ? N2 C10 1.478(2) . ? N2 C13 1.494(2) . ? N3 C7 1.142(2) . ? C1 C2 1.393(2) . ? C1 C6 1.398(2) . ? C1 C7 1.442(2) . ? C2 C3 1.381(2) . ? C2 H2 0.9500 . ? C3 C4 1.378(3) . ? C3 H3 0.9500 . ? C4 C5 1.383(2) . ? C5 C6 1.377(2) . ? C5 H5 0.9500 . ? C8 C9 1.493(2) . ? C9 C10 1.517(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.526(3) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C13 C15 1.517(2) . ? C13 C14 1.522(3) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.389(2) . ? C15 C20 1.395(2) . ? C16 C17 1.381(3) . ? C16 H16 0.9500 . ? C17 C18 1.376(3) . ? C17 H17 0.9500 . ? C18 C19 1.384(3) . ? C18 H18 0.9500 . ? C19 C20 1.382(2) . ? C19 H19 0.9500 . ? C20 H20 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 C8 N1 C12 124.74(14) . . ? C8 N1 C4 116.01(14) . . ? C12 N1 C4 119.18(13) . . ? C12 N2 C10 120.78(15) . . ? C12 N2 C13 120.49(14) . . ? C10 N2 C13 118.44(14) . . ? C2 C1 C6 119.31(15) . . ? C2 C1 C7 119.78(15) . . ? C6 C1 C7 120.89(15) . . ? C3 C2 C1 120.29(16) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 119.44(16) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 121.26(16) . . ? C3 C4 N1 120.83(15) . . ? C5 C4 N1 117.84(15) . . ? C6 C5 C4 119.32(16) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 120.33(15) . . ? C5 C6 Cl2 119.65(13) . . ? C1 C6 Cl2 120.02(13) . . ? N3 C7 C1 177.48(19) . . ? O1 C8 N1 119.70(16) . . ? O1 C8 C9 125.19(16) . . ? N1 C8 C9 115.10(15) . . ? C8 C9 C10 110.13(14) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? N2 C10 C9 107.23(14) . . ? N2 C10 C11 112.40(15) . . ? C9 C10 C11 112.06(16) . . ? N2 C10 H10 108.3 . . ? C9 C10 H10 108.3 . . ? C11 C10 H10 108.3 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 N1 115.38(14) . . ? N2 C12 S1 124.91(14) . . ? N1 C12 S1 119.71(12) . . ? N2 C13 C15 108.89(14) . . ? N2 C13 C14 110.44(15) . . ? C15 C13 C14 115.47(15) . . ? N2 C13 H13 107.2 . . ? C15 C13 H13 107.2 . . ? C14 C13 H13 107.2 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 118.22(16) . . ? C16 C15 C13 123.27(16) . . ? C20 C15 C13 118.49(15) . . ? C17 C16 C15 120.64(18) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 120.75(19) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 119.33(18) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C20 C19 C18 120.2(2) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C15 120.85(18) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.6(3) . . . . ? C7 C1 C2 C3 177.64(17) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 C5 1.7(3) . . . . ? C2 C3 C4 N1 178.62(16) . . . . ? C8 N1 C4 C3 -83.6(2) . . . . ? C12 N1 C4 C3 93.5(2) . . . . ? C8 N1 C4 C5 93.41(19) . . . . ? C12 N1 C4 C5 -89.6(2) . . . . ? C3 C4 C5 C6 -2.9(3) . . . . ? N1 C4 C5 C6 -179.84(16) . . . . ? C4 C5 C6 C1 2.2(3) . . . . ? C4 C5 C6 Cl2 -176.81(14) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? C7 C1 C6 C5 -178.76(17) . . . . ? C2 C1 C6 Cl2 178.52(15) . . . . ? C7 C1 C6 Cl2 0.3(2) . . . . ? C2 C1 C7 N3 -4(5) . . . . ? C6 C1 C7 N3 175(5) . . . . ? C12 N1 C8 O1 -176.73(16) . . . . ? C4 N1 C8 O1 0.1(2) . . . . ? C12 N1 C8 C9 3.4(2) . . . . ? C4 N1 C8 C9 -179.77(15) . . . . ? O1 C8 C9 C10 -146.99(17) . . . . ? N1 C8 C9 C10 32.9(2) . . . . ? C12 N2 C10 C9 50.3(2) . . . . ? C13 N2 C10 C9 -135.87(15) . . . . ? C12 N2 C10 C11 -73.3(2) . . . . ? C13 N2 C10 C11 100.54(18) . . . . ? C8 C9 C10 N2 -56.34(19) . . . . ? C8 C9 C10 C11 67.46(19) . . . . ? C10 N2 C12 N1 -15.3(2) . . . . ? C13 N2 C12 N1 170.97(14) . . . . ? C10 N2 C12 S1 164.31(13) . . . . ? C13 N2 C12 S1 -9.4(2) . . . . ? C8 N1 C12 N2 -14.0(2) . . . . ? C4 N1 C12 N2 169.27(15) . . . . ? C8 N1 C12 S1 166.38(13) . . . . ? C4 N1 C12 S1 -10.4(2) . . . . ? C12 N2 C13 C15 -137.44(15) . . . . ? C10 N2 C13 C15 48.69(19) . . . . ? C12 N2 C13 C14 94.80(18) . . . . ? C10 N2 C13 C14 -79.08(19) . . . . ? N2 C13 C15 C16 -115.83(19) . . . . ? C14 C13 C15 C16 9.0(3) . . . . ? N2 C13 C15 C20 63.0(2) . . . . ? C14 C13 C15 C20 -172.08(17) . . . . ? C20 C15 C16 C17 0.1(3) . . . . ? C13 C15 C16 C17 178.96(18) . . . . ? C15 C16 C17 C18 -0.8(3) . . . . ? C16 C17 C18 C19 0.9(3) . . . . ? C17 C18 C19 C20 -0.4(3) . . . . ? C18 C19 C20 C15 -0.3(3) . . . . ? C16 C15 C20 C19 0.4(3) . . . . ? C13 C15 C20 C19 -178.49(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.169 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.035 # Attachment 'niper3.cif' data_niper3 _database_code_depnum_ccdc_archive 'CCDC 772208' #TrackingRef 'niper3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Cl N3 O S' _chemical_formula_weight 383.88 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.5879(2) _cell_length_b 10.1912(2) _cell_length_c 24.2981(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1878.97(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13287 _cell_measurement_theta_min 3.3375 _cell_measurement_theta_max 32.8326 _exptl_crystal_description block _exptl_crystal_colour coloorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_T_min 0.9137 _exptl_absorpt_correction_T_max 0.9463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13418 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3299 _reflns_number_gt 3128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0386P)^2^+0.0671P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_number_reflns 3299 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0226 _refine_ls_R_factor_gt 0.0211 _refine_ls_wR_factor_ref 0.0571 _refine_ls_wR_factor_gt 0.0567 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.66951(5) 0.00970(4) -0.011547(16) 0.03176(11) Uani 1 1 d . . . Cl1 Cl 0.39929(5) 0.30605(3) -0.178369(14) 0.02941(10) Uani 1 1 d . . . O1 O 0.08079(16) -0.15630(10) -0.05451(4) 0.0336(3) Uani 1 1 d . . . N1 N 0.33500(16) -0.05096(11) -0.03193(4) 0.0212(3) Uani 1 1 d . . . N2 N 0.39701(16) 0.01007(12) 0.05829(4) 0.0225(2) Uani 1 1 d . . . N3 N 0.4677(2) 0.10278(14) -0.30077(5) 0.0375(4) Uani 1 1 d . . . C1 C 0.4168(2) 0.04526(14) -0.19837(5) 0.0226(3) Uani 1 1 d . . . C2 C 0.4152(2) -0.08564(14) -0.18212(6) 0.0270(3) Uani 1 1 d . . . H2 H 0.4311 -0.1527 -0.2088 0.032 Uiso 1 1 calc R . . C3 C 0.3909(2) -0.11895(14) -0.12750(5) 0.0242(3) Uani 1 1 d . . . H3 H 0.3904 -0.2084 -0.1165 0.029 Uiso 1 1 calc R . . C4 C 0.36717(18) -0.02012(14) -0.08906(5) 0.0206(3) Uani 1 1 d . . . C5 C 0.36737(18) 0.11046(14) -0.10432(5) 0.0212(3) Uani 1 1 d . . . H5 H 0.3498 0.1772 -0.0776 0.025 Uiso 1 1 calc R . . C6 C 0.3934(2) 0.14305(13) -0.15894(6) 0.0208(3) Uani 1 1 d . . . C7 C 0.4443(2) 0.07857(14) -0.25527(6) 0.0269(3) Uani 1 1 d . . . C8 C 0.46050(18) -0.00967(14) 0.00783(5) 0.0216(3) Uani 1 1 d . . . C9 C 0.1798(2) -0.11860(14) -0.01893(6) 0.0245(3) Uani 1 1 d . . . C10 C 0.1496(2) -0.13364(15) 0.04153(6) 0.0302(4) Uani 1 1 d . . . H10A H 0.2179 -0.2092 0.0557 0.036 Uiso 1 1 calc R . . H10B H 0.0231 -0.1499 0.0488 0.036 Uiso 1 1 calc R . . C11 C 0.20800(18) -0.00839(16) 0.07019(6) 0.0261(3) Uani 1 1 d . . . H11 H 0.1930 -0.0200 0.1108 0.031 Uiso 1 1 calc R . . C12 C 0.1003(2) 0.10975(16) 0.05201(6) 0.0311(3) Uani 1 1 d . . . H12A H 0.1378 0.1873 0.0728 0.047 Uiso 1 1 calc R . . H12B H -0.0249 0.0930 0.0590 0.047 Uiso 1 1 calc R . . H12C H 0.1186 0.1250 0.0126 0.047 Uiso 1 1 calc R . . C13 C 0.5169(2) 0.03738(15) 0.10544(6) 0.0281(4) Uani 1 1 d . . . H13 H 0.6347 0.0595 0.0895 0.034 Uiso 1 1 calc R . . C14 C 0.5409(3) -0.08620(18) 0.13948(7) 0.0432(5) Uani 1 1 d . . . H14A H 0.4294 -0.1087 0.1575 0.065 Uiso 1 1 calc R . . H14B H 0.6316 -0.0712 0.1675 0.065 Uiso 1 1 calc R . . H14C H 0.5773 -0.1585 0.1155 0.065 Uiso 1 1 calc R . . C15 C 0.4554(2) 0.15725(15) 0.13715(6) 0.0253(3) Uani 1 1 d . . . C16 C 0.4204(2) 0.15370(16) 0.19316(6) 0.0313(4) Uani 1 1 d . . . H16 H 0.4248 0.0726 0.2124 0.038 Uiso 1 1 calc R . . C17 C 0.3791(2) 0.26794(18) 0.22120(7) 0.0394(4) Uani 1 1 d . . . H17 H 0.3553 0.2643 0.2596 0.047 Uiso 1 1 calc R . . C18 C 0.3720(2) 0.38685(18) 0.19423(7) 0.0395(4) Uani 1 1 d . . . H18 H 0.3454 0.4648 0.2140 0.047 Uiso 1 1 calc R . . C19 C 0.4038(3) 0.39188(17) 0.13843(7) 0.0392(4) Uani 1 1 d . . . H19 H 0.3969 0.4731 0.1194 0.047 Uiso 1 1 calc R . . C20 C 0.4460(2) 0.27799(16) 0.11034(7) 0.0318(4) Uani 1 1 d . . . H20 H 0.4690 0.2822 0.0719 0.038 Uiso 1 1 calc R . . 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 0.02341(19) 0.0505(3) 0.02138(18) -0.00209(17) 0.00136(14) -0.00400(19) Cl1 0.0431(2) 0.02057(17) 0.02455(18) 0.00161(14) 0.00680(17) -0.00081(16) O1 0.0344(6) 0.0373(6) 0.0291(6) -0.0072(5) -0.0005(5) -0.0120(5) N1 0.0258(6) 0.0248(6) 0.0130(5) -0.0003(4) 0.0008(5) -0.0042(5) N2 0.0237(6) 0.0299(6) 0.0138(6) -0.0017(5) -0.0015(5) 0.0012(6) N3 0.0649(10) 0.0284(7) 0.0194(7) -0.0021(5) 0.0016(6) -0.0077(7) C1 0.0263(8) 0.0256(7) 0.0160(6) -0.0003(5) -0.0013(6) -0.0013(6) C2 0.0385(9) 0.0235(7) 0.0191(7) -0.0045(6) 0.0004(7) -0.0002(7) C3 0.0325(8) 0.0210(7) 0.0190(7) -0.0002(5) -0.0002(6) -0.0008(7) C4 0.0204(7) 0.0274(7) 0.0141(6) -0.0001(5) -0.0008(5) -0.0021(6) C5 0.0221(8) 0.0234(7) 0.0180(7) -0.0047(5) 0.0026(5) -0.0024(6) C6 0.0226(7) 0.0191(7) 0.0209(7) 0.0008(5) 0.0004(6) -0.0008(6) C7 0.0392(9) 0.0199(7) 0.0216(8) -0.0036(6) -0.0022(6) -0.0043(6) C8 0.0249(7) 0.0223(7) 0.0175(7) 0.0004(6) -0.0012(5) 0.0015(6) C9 0.0288(8) 0.0202(7) 0.0245(8) -0.0022(6) 0.0020(6) -0.0018(6) C10 0.0361(9) 0.0305(8) 0.0240(8) 0.0019(6) 0.0066(7) -0.0075(7) C11 0.0270(8) 0.0342(8) 0.0172(7) -0.0001(6) 0.0033(6) -0.0035(7) C12 0.0246(8) 0.0386(9) 0.0301(8) -0.0085(7) -0.0004(7) -0.0003(8) C13 0.0301(8) 0.0383(9) 0.0161(7) -0.0046(6) -0.0063(6) 0.0052(7) C14 0.0617(12) 0.0402(10) 0.0276(9) -0.0048(7) -0.0141(8) 0.0190(9) C15 0.0212(8) 0.0343(8) 0.0204(7) -0.0048(6) -0.0045(6) -0.0020(6) C16 0.0340(9) 0.0387(9) 0.0211(8) -0.0027(6) -0.0010(7) -0.0035(7) C17 0.0393(10) 0.0532(11) 0.0258(8) -0.0151(7) 0.0042(7) -0.0064(8) C18 0.0346(10) 0.0402(10) 0.0439(10) -0.0192(8) -0.0047(7) 0.0001(8) C19 0.0404(10) 0.0298(9) 0.0475(10) -0.0022(7) -0.0120(8) -0.0020(8) C20 0.0324(9) 0.0386(9) 0.0245(8) 0.0011(7) -0.0041(7) -0.0029(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 C8 1.6661(14) . ? Cl1 C6 1.7276(13) . ? O1 C9 1.2081(18) . ? N1 C9 1.4005(19) . ? N1 C8 1.4204(17) . ? N1 C4 1.4439(17) . ? N2 C8 1.3326(17) . ? N2 C11 1.4751(19) . ? N2 C13 1.4890(17) . ? N3 C7 1.1466(19) . ? C1 C2 1.3913(19) . ? C1 C6 1.394(2) . ? C1 C7 1.439(2) . ? C2 C3 1.3823(19) . ? C2 H2 0.9500 . ? C3 C4 1.3854(19) . ? C3 H3 0.9500 . ? C4 C5 1.382(2) . ? C5 C6 1.3822(19) . ? C5 H5 0.9500 . ? C9 C10 1.495(2) . ? C10 C11 1.520(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.521(2) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.518(2) . ? C13 C15 1.518(2) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.387(2) . ? C15 C20 1.394(2) . ? C16 C17 1.385(2) . ? C16 H16 0.9500 . ? C17 C18 1.379(3) . ? C17 H17 0.9500 . ? C18 C19 1.378(2) . ? C18 H18 0.9500 . ? C19 C20 1.384(2) . ? C19 H19 0.9500 . ? C20 H20 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 C9 N1 C8 123.78(11) . . ? C9 N1 C4 117.78(11) . . ? C8 N1 C4 118.43(11) . . ? C8 N2 C11 120.84(11) . . ? C8 N2 C13 121.02(12) . . ? C11 N2 C13 117.83(11) . . ? C2 C1 C6 119.30(12) . . ? C2 C1 C7 120.01(12) . . ? C6 C1 C7 120.68(13) . . ? C3 C2 C1 120.60(13) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 119.09(13) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 121.27(12) . . ? C5 C4 N1 117.90(12) . . ? C3 C4 N1 120.79(12) . . ? C4 C5 C6 119.30(12) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 120.43(13) . . ? C5 C6 Cl1 119.81(11) . . ? C1 C6 Cl1 119.76(11) . . ? N3 C7 C1 178.65(17) . . ? N2 C8 N1 115.35(12) . . ? N2 C8 S1 125.89(11) . . ? N1 C8 S1 118.76(10) . . ? O1 C9 N1 121.20(13) . . ? O1 C9 C10 125.12(14) . . ? N1 C9 C10 113.64(12) . . ? C9 C10 C11 108.64(12) . . ? C9 C10 H10A 110.0 . . ? C11 C10 H10A 110.0 . . ? C9 C10 H10B 110.0 . . ? C11 C10 H10B 110.0 . . ? H10A C10 H10B 108.3 . . ? N2 C11 C10 107.49(12) . . ? N2 C11 C12 111.39(13) . . ? C10 C11 C12 112.04(13) . . ? N2 C11 H11 108.6 . . ? C10 C11 H11 108.6 . . ? C12 C11 H11 108.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C14 109.73(13) . . ? N2 C13 C15 110.69(12) . . ? C14 C13 C15 115.35(13) . . ? N2 C13 H13 106.9 . . ? C14 C13 H13 106.9 . . ? C15 C13 H13 106.9 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 118.14(14) . . ? C16 C15 C13 122.40(14) . . ? C20 C15 C13 119.27(13) . . ? C17 C16 C15 120.27(15) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 120.92(15) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 119.57(16) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C20 119.64(16) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C19 C20 C15 121.44(15) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.0(2) . . . . ? C7 C1 C2 C3 179.32(15) . . . . ? C1 C2 C3 C4 0.3(2) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C2 C3 C4 N1 177.77(14) . . . . ? C9 N1 C4 C5 113.96(14) . . . . ? C8 N1 C4 C5 -65.18(17) . . . . ? C9 N1 C4 C3 -63.83(18) . . . . ? C8 N1 C4 C3 117.03(15) . . . . ? C3 C4 C5 C6 -0.6(2) . . . . ? N1 C4 C5 C6 -178.40(13) . . . . ? C4 C5 C6 C1 0.9(2) . . . . ? C4 C5 C6 Cl1 -178.45(11) . . . . ? C2 C1 C6 C5 -0.6(2) . . . . ? C7 C1 C6 C5 -179.90(14) . . . . ? C2 C1 C6 Cl1 178.76(13) . . . . ? C7 C1 C6 Cl1 -0.6(2) . . . . ? C2 C1 C7 N3 -23(8) . . . . ? C6 C1 C7 N3 157(8) . . . . ? C11 N2 C8 N1 -1.06(19) . . . . ? C13 N2 C8 N1 172.38(12) . . . . ? C11 N2 C8 S1 178.99(11) . . . . ? C13 N2 C8 S1 -7.6(2) . . . . ? C9 N1 C8 N2 -25.96(19) . . . . ? C4 N1 C8 N2 153.12(12) . . . . ? C9 N1 C8 S1 153.99(11) . . . . ? C4 N1 C8 S1 -26.92(17) . . . . ? C8 N1 C9 O1 -176.93(14) . . . . ? C4 N1 C9 O1 4.0(2) . . . . ? C8 N1 C9 C10 5.0(2) . . . . ? C4 N1 C9 C10 -174.05(13) . . . . ? O1 C9 C10 C11 -139.84(15) . . . . ? N1 C9 C10 C11 38.10(18) . . . . ? C8 N2 C11 C10 43.20(18) . . . . ? C13 N2 C11 C10 -130.44(13) . . . . ? C8 N2 C11 C12 -79.88(16) . . . . ? C13 N2 C11 C12 106.48(14) . . . . ? C9 C10 C11 N2 -60.08(16) . . . . ? C9 C10 C11 C12 62.60(17) . . . . ? C8 N2 C13 C14 -101.35(16) . . . . ? C11 N2 C13 C14 72.28(17) . . . . ? C8 N2 C13 C15 130.21(14) . . . . ? C11 N2 C13 C15 -56.16(17) . . . . ? N2 C13 C15 C16 124.19(15) . . . . ? C14 C13 C15 C16 -1.1(2) . . . . ? N2 C13 C15 C20 -60.75(19) . . . . ? C14 C13 C15 C20 173.91(15) . . . . ? C20 C15 C16 C17 -0.6(2) . . . . ? C13 C15 C16 C17 174.51(16) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C16 C17 C18 C19 1.0(3) . . . . ? C17 C18 C19 C20 -1.3(3) . . . . ? C18 C19 C20 C15 0.7(3) . . . . ? C16 C15 C20 C19 0.3(2) . . . . ? C13 C15 C20 C19 -174.97(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.133 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.041 # Attachment 'enp174.cif' data_enp174 _database_code_depnum_ccdc_archive 'CCDC 772209' #TrackingRef 'enp174.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H23 Cl2 N3 O S' _chemical_formula_weight 508.44 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' Cl Cl 0.1484 0.1585 '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) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.7540(9) _cell_length_b 9.3273(8) _cell_length_c 13.3001(12) _cell_angle_alpha 90.00 _cell_angle_beta 89.90 _cell_angle_gamma 90.00 _cell_volume 1210.02(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6069 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 25.92 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8751 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6817 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.94 _reflns_number_total 4421 _reflns_number_gt 4266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0884P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(5) _refine_ls_number_reflns 4421 _refine_ls_number_parameters 313 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.2217(2) 0.5499(3) 0.16852(18) 0.0152(5) Uani 1 1 d . . . C2 C 0.2248(2) 0.4596(3) 0.07405(17) 0.0142(5) Uani 1 1 d . . . H2 H 0.3222 0.4549 0.0507 0.017 Uiso 1 1 calc R . . C3 C 0.1819(2) 0.3078(3) 0.10418(17) 0.0146(5) Uani 1 1 d . . . H3 H 0.1857 0.2455 0.0431 0.018 Uiso 1 1 calc R . . C4 C 0.3236(2) 0.3385(3) 0.25384(18) 0.0150(5) Uani 1 1 d . . . C5 C 0.2605(3) 0.5580(3) 0.34772(17) 0.0155(5) Uani 1 1 d . . . C6 C 0.3547(3) 0.6647(3) 0.36934(18) 0.0182(5) Uani 1 1 d . . . H6 H 0.4309 0.6806 0.3262 0.022 Uiso 1 1 calc R . . C7 C 0.3366(3) 0.7476(3) 0.45428(19) 0.0191(5) Uani 1 1 d . . . H7 H 0.4008 0.8210 0.4696 0.023 Uiso 1 1 calc R . . C8 C 0.2250(3) 0.7244(3) 0.51760(19) 0.0185(5) Uani 1 1 d . . . C9 C 0.1333(3) 0.6142(3) 0.49528(19) 0.0197(5) Uani 1 1 d . . . C10 C 0.1497(3) 0.5319(3) 0.40988(19) 0.0178(5) Uani 1 1 d . . . H10 H 0.0858 0.4585 0.3941 0.021 Uiso 1 1 calc R . . C11 C 0.2027(3) 0.8149(3) 0.60414(19) 0.0216(6) Uani 1 1 d . . . C12 C 0.0377(3) 0.2989(3) 0.14847(19) 0.0210(5) Uani 1 1 d . . . H12A H 0.0195 0.2006 0.1707 0.031 Uiso 1 1 calc R . . H12B H -0.0294 0.3263 0.0972 0.031 Uiso 1 1 calc R . . H12C H 0.0304 0.3642 0.2060 0.031 Uiso 1 1 calc R . . C13 C 0.3436(3) 0.1098(3) 0.16496(18) 0.0163(5) Uani 1 1 d . . . C14 C 0.3651(2) 0.0791(3) 0.05364(18) 0.0158(5) Uani 1 1 d . . . C15 C 0.2999(3) -0.0341(3) 0.00406(19) 0.0178(5) Uani 1 1 d . . . H15 H 0.2451 -0.1000 0.0409 0.021 Uiso 1 1 calc R . . C16 C 0.3155(3) -0.0502(3) -0.09955(19) 0.0197(5) Uani 1 1 d . . . H16 H 0.2714 -0.1275 -0.1329 0.024 Uiso 1 1 calc R . . C17 C 0.3946(3) 0.0452(3) -0.15453(19) 0.0202(5) Uani 1 1 d . . . H17 H 0.4030 0.0346 -0.2253 0.024 Uiso 1 1 calc R . . C18 C 0.4615(3) 0.1563(3) -0.10541(19) 0.0190(5) Uani 1 1 d . . . H18 H 0.5167 0.2215 -0.1424 0.023 Uiso 1 1 calc R . . C19 C 0.4475(2) 0.1719(3) -0.00187(19) 0.0176(5) Uani 1 1 d . . . H19 H 0.4950 0.2470 0.0315 0.021 Uiso 1 1 calc R . . C20 C 0.2561(3) 0.0022(3) 0.2223(2) 0.0226(6) Uani 1 1 d . . . H20A H 0.2479 0.0325 0.2926 0.034 Uiso 1 1 calc R . . H20B H 0.2994 -0.0925 0.2193 0.034 Uiso 1 1 calc R . . H20C H 0.1648 -0.0026 0.1919 0.034 Uiso 1 1 calc R . . C21 C 0.1409(3) 0.5286(3) -0.01037(19) 0.0184(5) Uani 1 1 d . . . H21A H 0.0420 0.5167 0.0044 0.022 Uiso 1 1 calc R . . H21B H 0.1608 0.6326 -0.0126 0.022 Uiso 1 1 calc R . . C22 C 0.1723(3) 0.4632(3) -0.11184(18) 0.0174(5) Uani 1 1 d . . . C23 C 0.1012(3) 0.3438(3) -0.14706(19) 0.0188(5) Uani 1 1 d . . . H23 H 0.0297 0.3037 -0.1075 0.023 Uiso 1 1 calc R . . C24 C 0.1340(3) 0.2825(3) -0.23991(18) 0.0214(5) Uani 1 1 d . . . H24 H 0.0859 0.2005 -0.2635 0.026 Uiso 1 1 calc R . . C25 C 0.2372(3) 0.3429(3) -0.29675(19) 0.0209(5) Uani 1 1 d . . . C26 C 0.3085(3) 0.4612(3) -0.26441(19) 0.0220(6) Uani 1 1 d . . . H26 H 0.3796 0.5010 -0.3046 0.026 Uiso 1 1 calc R . . C27 C 0.2752(3) 0.5215(3) -0.1721(2) 0.0212(5) Uani 1 1 d . . . H27 H 0.3234 0.6040 -0.1496 0.025 Uiso 1 1 calc R . . Cl1 Cl -0.00465(7) 0.58158(9) 0.57463(5) 0.02971(19) Uani 1 1 d . . . Cl2 Cl 0.27788(7) 0.26857(8) -0.41324(5) 0.02986(18) Uani 1 1 d . . . H13 H 0.441(3) 0.120(3) 0.199(2) 0.017(7) Uiso 1 1 d . . . N1 N 0.2695(2) 0.4795(2) 0.25430(15) 0.0147(4) Uani 1 1 d . . . N2 N 0.2866(2) 0.2574(2) 0.17610(15) 0.0145(4) Uani 1 1 d . . . N3 N 0.1841(2) 0.8900(3) 0.67066(18) 0.0291(6) Uani 1 1 d . . . O1 O 0.18153(18) 0.67230(19) 0.17220(13) 0.0196(4) Uani 1 1 d . . . S1 S 0.42661(6) 0.28748(7) 0.34699(4) 0.02004(16) 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 0.0121(11) 0.0183(13) 0.0153(12) -0.0019(10) -0.0012(9) -0.0012(9) C2 0.0156(11) 0.0129(12) 0.0140(11) -0.0016(10) -0.0022(9) 0.0004(9) C3 0.0140(11) 0.0152(12) 0.0147(11) -0.0009(9) -0.0027(9) 0.0018(9) C4 0.0160(12) 0.0140(11) 0.0149(11) -0.0001(9) 0.0010(9) 0.0001(9) C5 0.0189(12) 0.0164(12) 0.0111(11) -0.0042(9) -0.0035(9) 0.0025(10) C6 0.0192(12) 0.0202(13) 0.0154(12) -0.0017(10) -0.0008(10) -0.0008(10) C7 0.0204(12) 0.0200(13) 0.0169(12) -0.0049(10) -0.0032(10) -0.0009(10) C8 0.0220(13) 0.0200(13) 0.0135(11) -0.0013(10) -0.0044(10) 0.0032(10) C9 0.0167(12) 0.0275(14) 0.0150(12) 0.0005(10) 0.0006(10) -0.0005(10) C10 0.0168(12) 0.0200(12) 0.0165(12) -0.0010(10) -0.0027(10) -0.0016(10) C11 0.0182(12) 0.0271(15) 0.0196(13) -0.0014(11) -0.0013(10) 0.0011(11) C12 0.0206(13) 0.0206(13) 0.0218(12) -0.0019(11) -0.0024(10) -0.0007(11) C13 0.0201(12) 0.0119(12) 0.0168(12) -0.0001(10) -0.0016(10) 0.0031(9) C14 0.0146(11) 0.0162(12) 0.0167(11) 0.0000(10) -0.0024(9) 0.0039(10) C15 0.0180(12) 0.0156(12) 0.0199(12) -0.0001(10) -0.0001(10) 0.0038(10) C16 0.0207(13) 0.0164(12) 0.0221(13) -0.0050(10) -0.0047(10) 0.0031(10) C17 0.0213(13) 0.0245(14) 0.0148(12) -0.0036(10) -0.0007(10) 0.0058(10) C18 0.0178(12) 0.0206(14) 0.0186(12) 0.0012(10) 0.0021(10) 0.0018(10) C19 0.0157(12) 0.0196(13) 0.0175(12) -0.0011(10) -0.0019(9) 0.0023(10) C20 0.0319(15) 0.0168(14) 0.0191(13) 0.0006(10) 0.0034(11) 0.0004(11) C21 0.0233(13) 0.0164(12) 0.0157(12) -0.0007(10) -0.0055(10) 0.0036(10) C22 0.0210(12) 0.0168(12) 0.0144(11) 0.0014(10) -0.0060(10) 0.0034(10) C23 0.0202(13) 0.0203(13) 0.0159(12) 0.0019(10) -0.0028(10) -0.0014(10) C24 0.0238(13) 0.0225(13) 0.0179(12) -0.0034(12) -0.0053(10) -0.0036(11) C25 0.0249(14) 0.0259(13) 0.0119(11) -0.0004(10) -0.0040(10) 0.0051(11) C26 0.0211(13) 0.0278(15) 0.0172(12) 0.0040(11) -0.0001(10) -0.0021(11) C27 0.0211(13) 0.0212(13) 0.0214(13) 0.0010(10) -0.0054(10) -0.0030(10) Cl1 0.0239(3) 0.0447(4) 0.0204(3) -0.0062(3) 0.0070(3) -0.0070(3) Cl2 0.0347(4) 0.0382(4) 0.0167(3) -0.0062(3) 0.0011(3) 0.0031(3) N1 0.0174(10) 0.0150(10) 0.0117(9) -0.0030(8) -0.0025(8) 0.0022(8) N2 0.0167(10) 0.0144(11) 0.0123(9) -0.0002(8) -0.0022(8) 0.0005(8) N3 0.0266(13) 0.0372(14) 0.0235(12) -0.0097(11) 0.0020(10) -0.0005(11) O1 0.0254(10) 0.0138(9) 0.0197(9) -0.0024(7) -0.0046(7) 0.0011(7) S1 0.0240(3) 0.0217(3) 0.0144(3) -0.0014(2) -0.0060(2) 0.0040(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 O1 1.208(3) . ? C1 N1 1.397(3) . ? C1 C2 1.513(3) . ? C2 C3 1.530(3) . ? C2 C21 1.532(3) . ? C2 H2 1.0000 . ? C3 N2 1.478(3) . ? C3 C12 1.526(3) . ? C3 H3 1.0000 . ? C4 N2 1.331(3) . ? C4 N1 1.417(3) . ? C4 S1 1.666(2) . ? C5 C10 1.382(4) . ? C5 C6 1.385(4) . ? C5 N1 1.445(3) . ? C6 C7 1.380(4) . ? C6 H6 0.9500 . ? C7 C8 1.392(4) . ? C7 H7 0.9500 . ? C8 C9 1.395(4) . ? C8 C11 1.443(4) . ? C9 C10 1.380(4) . ? C9 Cl1 1.736(3) . ? C10 H10 0.9500 . ? C11 N3 1.143(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N2 1.492(3) . ? C13 C20 1.521(4) . ? C13 C14 1.522(3) . ? C13 H13 1.05(3) . ? C14 C19 1.392(4) . ? C14 C15 1.398(4) . ? C15 C16 1.394(3) . ? C15 H15 0.9500 . ? C16 C17 1.385(4) . ? C16 H16 0.9500 . ? C17 C18 1.388(4) . ? C17 H17 0.9500 . ? C18 C19 1.391(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.512(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.393(4) . ? C22 C27 1.393(4) . ? C23 C24 1.397(4) . ? C23 H23 0.9500 . ? C24 C25 1.378(4) . ? C24 H24 0.9500 . ? C25 C26 1.374(4) . ? C25 Cl2 1.743(3) . ? C26 C27 1.389(4) . ? C26 H26 0.9500 . ? C27 H27 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 C1 N1 121.3(2) . . ? O1 C1 C2 124.4(2) . . ? N1 C1 C2 114.2(2) . . ? C1 C2 C3 107.0(2) . . ? C1 C2 C21 111.4(2) . . ? C3 C2 C21 115.7(2) . . ? C1 C2 H2 107.4 . . ? C3 C2 H2 107.4 . . ? C21 C2 H2 107.4 . . ? N2 C3 C12 111.8(2) . . ? N2 C3 C2 105.97(19) . . ? C12 C3 C2 113.8(2) . . ? N2 C3 H3 108.4 . . ? C12 C3 H3 108.4 . . ? C2 C3 H3 108.4 . . ? N2 C4 N1 115.4(2) . . ? N2 C4 S1 125.4(2) . . ? N1 C4 S1 119.14(18) . . ? C10 C5 C6 121.4(2) . . ? C10 C5 N1 118.1(2) . . ? C6 C5 N1 120.3(2) . . ? C7 C6 C5 119.3(2) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 120.4(2) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C9 119.1(2) . . ? C7 C8 C11 120.5(2) . . ? C9 C8 C11 120.3(2) . . ? C10 C9 C8 120.8(2) . . ? C10 C9 Cl1 119.4(2) . . ? C8 C9 Cl1 119.8(2) . . ? C9 C10 C5 118.9(2) . . ? C9 C10 H10 120.5 . . ? C5 C10 H10 120.5 . . ? N3 C11 C8 177.8(3) . . ? C3 C12 H12A 109.5 . . ? C3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C20 110.5(2) . . ? N2 C13 C14 108.70(19) . . ? C20 C13 C14 116.1(2) . . ? N2 C13 H13 102.1(16) . . ? C20 C13 H13 110.3(16) . . ? C14 C13 H13 108.1(15) . . ? C19 C14 C15 118.8(2) . . ? C19 C14 C13 118.5(2) . . ? C15 C14 C13 122.6(2) . . ? C16 C15 C14 119.9(2) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 120.9(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 119.5(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 119.9(2) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C14 121.0(2) . . ? C18 C19 H19 119.5 . . ? C14 C19 H19 119.5 . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C2 112.1(2) . . ? C22 C21 H21A 109.2 . . ? C2 C21 H21A 109.2 . . ? C22 C21 H21B 109.2 . . ? C2 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C23 C22 C27 118.5(2) . . ? C23 C22 C21 121.5(2) . . ? C27 C22 C21 120.0(2) . . ? C22 C23 C24 120.7(2) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C25 C24 C23 118.9(3) . . ? C25 C24 H24 120.6 . . ? C23 C24 H24 120.6 . . ? C26 C25 C24 121.8(2) . . ? C26 C25 Cl2 118.9(2) . . ? C24 C25 Cl2 119.4(2) . . ? C25 C26 C27 119.0(2) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C26 C27 C22 121.1(3) . . ? C26 C27 H27 119.4 . . ? C22 C27 H27 119.4 . . ? C1 N1 C4 123.9(2) . . ? C1 N1 C5 116.4(2) . . ? C4 N1 C5 119.7(2) . . ? C4 N2 C3 120.7(2) . . ? C4 N2 C13 120.0(2) . . ? C3 N2 C13 119.17(19) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.411 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.057 # Attachment 'enp176.cif' data_enp176 _database_code_depnum_ccdc_archive 'CCDC 772210' #TrackingRef 'enp176.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H23 Cl2 N3 O S' _chemical_formula_weight 508.44 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 '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) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.8114(11) _cell_length_b 10.9871(11) _cell_length_c 11.0108(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.048(2) _cell_angle_gamma 90.00 _cell_volume 1250.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8302 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 25.96 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.369 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8636 _exptl_absorpt_correction_T_max 0.9366 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9363 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.96 _reflns_number_total 4769 _reflns_number_gt 4645 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0363P)^2^+0.1800P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 4769 _refine_ls_number_parameters 309 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0694 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.81173(17) 0.85609(16) 0.34071(16) 0.0191(4) Uani 1 1 d . . . C2 C 0.77253(18) 0.77968(17) 0.43680(16) 0.0192(4) Uani 1 1 d . . . H2 H 0.6824 0.8041 0.4329 0.023 Uiso 1 1 calc R . . C3 C 0.76668(17) 0.64696(17) 0.39337(16) 0.0182(4) Uani 1 1 d . . . H3 H 0.7360 0.5967 0.4545 0.022 Uiso 1 1 calc R . . C4 C 0.66391(15) 0.72277(17) 0.17871(15) 0.0166(3) Uani 1 1 d . . . C5 C 0.78067(16) 0.89147(17) 0.11706(15) 0.0179(3) Uani 1 1 d . . . C6 C 0.71413(17) 0.99878(17) 0.08110(16) 0.0200(4) Uani 1 1 d . . . H6 H 0.6486 1.0224 0.1179 0.024 Uiso 1 1 calc R . . C7 C 0.74333(18) 1.07180(17) -0.00873(17) 0.0212(4) Uani 1 1 d . . . H7 H 0.6986 1.1464 -0.0331 0.025 Uiso 1 1 calc R . . C8 C 0.83885(17) 1.03592(18) -0.06385(16) 0.0200(4) Uani 1 1 d . . . C9 C 0.90428(16) 0.92708(19) -0.02613(16) 0.0210(4) Uani 1 1 d . . . C10 C 0.87664(17) 0.85366(18) 0.06451(16) 0.0215(4) Uani 1 1 d . . . H10 H 0.9219 0.7795 0.0902 0.026 Uiso 1 1 calc R . . C11 C 0.86520(17) 1.11212(19) -0.15929(17) 0.0236(4) Uani 1 1 d . . . C12 C 0.89653(18) 0.59593(18) 0.38934(17) 0.0233(4) Uani 1 1 d . . . H12A H 0.9301 0.6454 0.3320 0.035 Uiso 1 1 calc R . . H12B H 0.8851 0.5118 0.3586 0.035 Uiso 1 1 calc R . . H12C H 0.9578 0.5979 0.4748 0.035 Uiso 1 1 calc R . . C13 C 0.85650(19) 0.79831(18) 0.57475(16) 0.0217(4) Uani 1 1 d . . . H13A H 0.9479 0.7790 0.5826 0.026 Uiso 1 1 calc R . . H13B H 0.8516 0.8841 0.6003 0.026 Uiso 1 1 calc R . . C14 C 0.80671(17) 0.71482(19) 0.65961(15) 0.0204(4) Uani 1 1 d . . . C15 C 0.86896(18) 0.60622(19) 0.70561(17) 0.0228(4) Uani 1 1 d . . . H15 H 0.9521 0.5904 0.6964 0.027 Uiso 1 1 calc R . . C16 C 0.81183(18) 0.52031(18) 0.76488(17) 0.0247(4) Uani 1 1 d . . . H16 H 0.8551 0.4462 0.7956 0.030 Uiso 1 1 calc R . . C17 C 0.69104(19) 0.54453(18) 0.77833(17) 0.0233(4) Uani 1 1 d . . . C18 C 0.62858(19) 0.65349(19) 0.73834(17) 0.0250(4) Uani 1 1 d . . . H18 H 0.5473 0.6707 0.7514 0.030 Uiso 1 1 calc R . . C19 C 0.68718(19) 0.73725(18) 0.67871(16) 0.0231(4) Uani 1 1 d . . . H19 H 0.6445 0.8121 0.6501 0.028 Uiso 1 1 calc R . . C20 C 0.56511(17) 0.54653(17) 0.25349(17) 0.0191(4) Uani 1 1 d . . . H20 H 0.5215 0.5356 0.1606 0.023 Uiso 1 1 calc R . . C21 C 0.62593(16) 0.42596(18) 0.30659(16) 0.0202(4) Uani 1 1 d . . . C22 C 0.63085(18) 0.38508(19) 0.42767(18) 0.0249(4) Uani 1 1 d . . . H22 H 0.5891 0.4305 0.4778 0.030 Uiso 1 1 calc R . . C23 C 0.6959(2) 0.2791(2) 0.4756(2) 0.0348(5) Uani 1 1 d . . . H23 H 0.6984 0.2525 0.5584 0.042 Uiso 1 1 calc R . . C24 C 0.7566(2) 0.2120(2) 0.4051(2) 0.0400(6) Uani 1 1 d . . . H24 H 0.8018 0.1397 0.4390 0.048 Uiso 1 1 calc R . . C25 C 0.7517(2) 0.25054(19) 0.2838(2) 0.0364(5) Uani 1 1 d . . . H25 H 0.7935 0.2043 0.2344 0.044 Uiso 1 1 calc R . . C26 C 0.68590(19) 0.35660(19) 0.23412(19) 0.0277(4) Uani 1 1 d . . . H26 H 0.6818 0.3818 0.1505 0.033 Uiso 1 1 calc R . . C27 C 0.46573(18) 0.59554(18) 0.31432(18) 0.0240(4) Uani 1 1 d . . . H27A H 0.4309 0.6727 0.2739 0.036 Uiso 1 1 calc R . . H27B H 0.5070 0.6089 0.4052 0.036 Uiso 1 1 calc R . . H27C H 0.3953 0.5366 0.3030 0.036 Uiso 1 1 calc R . . Cl1 Cl 1.02610(4) 0.88414(5) -0.09076(4) 0.02952(12) Uani 1 1 d . . . Cl2 Cl 0.61458(5) 0.43424(5) 0.84548(5) 0.03094(12) Uani 1 1 d . . . N1 N 0.75571(15) 0.81741(14) 0.21515(13) 0.0186(3) Uani 1 1 d . . . N2 N 0.66857(14) 0.63942(14) 0.26857(13) 0.0177(3) Uani 1 1 d . . . N3 N 0.88220(16) 1.17544(18) -0.23518(15) 0.0300(4) Uani 1 1 d . . . O1 O 0.88387(13) 0.94213(13) 0.36468(11) 0.0250(3) Uani 1 1 d . . . S1 S 0.56145(4) 0.72253(4) 0.03196(4) 0.02044(10) 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 0.0184(9) 0.0185(9) 0.0195(8) -0.0005(7) 0.0043(7) 0.0005(7) C2 0.0198(9) 0.0212(10) 0.0161(8) -0.0005(7) 0.0045(7) -0.0027(7) C3 0.0185(9) 0.0195(9) 0.0154(8) 0.0019(7) 0.0034(7) -0.0012(7) C4 0.0137(8) 0.0181(8) 0.0188(8) -0.0008(7) 0.0060(6) 0.0007(7) C5 0.0172(8) 0.0195(9) 0.0165(8) 0.0008(7) 0.0042(6) -0.0042(7) C6 0.0182(9) 0.0235(10) 0.0196(8) -0.0008(7) 0.0076(7) -0.0013(7) C7 0.0200(9) 0.0200(9) 0.0230(9) 0.0033(7) 0.0054(7) 0.0002(7) C8 0.0192(9) 0.0244(10) 0.0163(8) 0.0008(7) 0.0049(7) -0.0050(8) C9 0.0162(8) 0.0299(10) 0.0181(8) -0.0028(8) 0.0068(7) -0.0021(8) C10 0.0196(9) 0.0233(10) 0.0210(8) 0.0010(7) 0.0054(7) 0.0022(7) C11 0.0161(9) 0.0331(11) 0.0205(9) 0.0018(8) 0.0035(7) -0.0013(8) C12 0.0206(9) 0.0237(10) 0.0244(9) -0.0011(7) 0.0044(7) 0.0011(8) C13 0.0229(10) 0.0227(10) 0.0182(8) -0.0008(7) 0.0039(7) -0.0042(8) C14 0.0253(9) 0.0215(9) 0.0135(7) -0.0030(7) 0.0040(7) -0.0036(8) C15 0.0204(9) 0.0282(11) 0.0200(9) 0.0008(7) 0.0061(7) 0.0011(8) C16 0.0273(10) 0.0235(10) 0.0223(9) 0.0052(7) 0.0057(8) 0.0044(8) C17 0.0290(10) 0.0241(10) 0.0193(9) 0.0022(7) 0.0110(8) -0.0032(8) C18 0.0265(10) 0.0297(11) 0.0228(9) -0.0010(8) 0.0134(8) 0.0041(8) C19 0.0302(10) 0.0216(10) 0.0181(8) 0.0018(7) 0.0081(7) 0.0044(8) C20 0.0184(9) 0.0196(9) 0.0180(8) 0.0010(7) 0.0032(7) -0.0050(7) C21 0.0153(8) 0.0191(9) 0.0231(8) -0.0013(8) 0.0007(7) -0.0046(7) C22 0.0206(9) 0.0228(10) 0.0289(9) 0.0004(8) 0.0037(7) -0.0051(8) C23 0.0291(11) 0.0287(11) 0.0398(12) 0.0139(10) -0.0003(9) -0.0066(9) C24 0.0253(11) 0.0199(11) 0.0637(15) 0.0050(11) -0.0046(10) -0.0003(9) C25 0.0257(11) 0.0214(11) 0.0589(15) -0.0153(10) 0.0071(10) -0.0008(8) C26 0.0231(10) 0.0285(11) 0.0291(10) -0.0084(8) 0.0040(8) -0.0057(8) C27 0.0217(9) 0.0218(10) 0.0295(10) 0.0029(8) 0.0089(8) 0.0011(8) Cl1 0.0255(2) 0.0392(3) 0.0288(2) 0.0002(2) 0.01570(19) 0.0035(2) Cl2 0.0364(3) 0.0273(2) 0.0346(3) 0.0054(2) 0.0190(2) -0.0022(2) N1 0.0198(8) 0.0199(8) 0.0164(7) 0.0019(6) 0.0060(6) -0.0025(6) N2 0.0171(7) 0.0181(8) 0.0166(7) 0.0012(6) 0.0031(6) -0.0019(6) N3 0.0242(9) 0.0419(11) 0.0250(8) 0.0078(8) 0.0088(7) -0.0046(8) O1 0.0288(7) 0.0217(7) 0.0227(6) 0.0009(5) 0.0049(5) -0.0080(6) S1 0.0219(2) 0.0231(2) 0.01484(18) 0.00108(17) 0.00294(16) -0.00334(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 O1 1.205(2) . ? C1 N1 1.403(2) . ? C1 C2 1.506(2) . ? C2 C3 1.530(3) . ? C2 C13 1.538(2) . ? C2 H2 1.0000 . ? C3 N2 1.472(2) . ? C3 C12 1.524(3) . ? C3 H3 1.0000 . ? C4 N2 1.338(2) . ? C4 N1 1.412(2) . ? C4 S1 1.6698(16) . ? C5 C6 1.377(3) . ? C5 C10 1.391(2) . ? C5 N1 1.440(2) . ? C6 C7 1.380(3) . ? C6 H6 0.9500 . ? C7 C8 1.399(3) . ? C7 H7 0.9500 . ? C8 C9 1.390(3) . ? C8 C11 1.436(3) . ? C9 C10 1.382(3) . ? C9 Cl1 1.7358(18) . ? C10 H10 0.9500 . ? C11 N3 1.143(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.516(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.390(3) . ? C14 C19 1.391(3) . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 C17 1.383(3) . ? C16 H16 0.9500 . ? C17 C18 1.382(3) . ? C17 Cl2 1.7483(19) . ? C18 C19 1.387(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 N2 1.487(2) . ? C20 C21 1.518(3) . ? C20 C27 1.521(3) . ? C20 H20 1.0000 . ? C21 C26 1.393(3) . ? C21 C22 1.393(3) . ? C22 C23 1.382(3) . ? C22 H22 0.9500 . ? C23 C24 1.370(4) . ? C23 H23 0.9500 . ? C24 C25 1.387(4) . ? C24 H24 0.9500 . ? C25 C26 1.391(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 C1 N1 121.23(16) . . ? O1 C1 C2 125.54(16) . . ? N1 C1 C2 113.23(15) . . ? C1 C2 C3 107.83(14) . . ? C1 C2 C13 114.43(15) . . ? C3 C2 C13 113.20(15) . . ? C1 C2 H2 107.0 . . ? C3 C2 H2 107.0 . . ? C13 C2 H2 107.0 . . ? N2 C3 C12 111.71(14) . . ? N2 C3 C2 107.33(14) . . ? C12 C3 C2 113.93(16) . . ? N2 C3 H3 107.9 . . ? C12 C3 H3 107.9 . . ? C2 C3 H3 107.9 . . ? N2 C4 N1 115.01(14) . . ? N2 C4 S1 125.79(14) . . ? N1 C4 S1 119.20(13) . . ? C6 C5 C10 121.76(16) . . ? C6 C5 N1 120.17(16) . . ? C10 C5 N1 118.02(16) . . ? C5 C6 C7 119.58(17) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C8 120.00(17) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 119.26(17) . . ? C9 C8 C11 121.85(17) . . ? C7 C8 C11 118.89(17) . . ? C10 C9 C8 121.27(17) . . ? C10 C9 Cl1 119.21(15) . . ? C8 C9 Cl1 119.50(14) . . ? C9 C10 C5 118.12(17) . . ? C9 C10 H10 120.9 . . ? C5 C10 H10 120.9 . . ? N3 C11 C8 177.4(2) . . ? C3 C12 H12A 109.5 . . ? C3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C2 108.34(15) . . ? C14 C13 H13A 110.0 . . ? C2 C13 H13A 110.0 . . ? C14 C13 H13B 110.0 . . ? C2 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? C15 C14 C19 117.97(17) . . ? C15 C14 C13 121.49(17) . . ? C19 C14 C13 119.96(17) . . ? C14 C15 C16 121.28(17) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 118.87(18) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C18 C17 C16 121.43(18) . . ? C18 C17 Cl2 119.20(15) . . ? C16 C17 Cl2 119.37(15) . . ? C17 C18 C19 118.52(17) . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? C18 C19 C14 121.85(18) . . ? C18 C19 H19 119.1 . . ? C14 C19 H19 119.1 . . ? N2 C20 C21 109.22(14) . . ? N2 C20 C27 108.24(15) . . ? C21 C20 C27 114.93(15) . . ? N2 C20 H20 108.1 . . ? C21 C20 H20 108.1 . . ? C27 C20 H20 108.1 . . ? C26 C21 C22 118.57(18) . . ? C26 C21 C20 118.60(16) . . ? C22 C21 C20 122.73(17) . . ? C23 C22 C21 120.6(2) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 120.8(2) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 119.4(2) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C24 C25 C26 120.4(2) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 120.20(19) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? C20 C27 H27A 109.5 . . ? C20 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C20 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C1 N1 C4 124.58(14) . . ? C1 N1 C5 116.51(14) . . ? C4 N1 C5 118.28(14) . . ? C4 N2 C3 120.83(14) . . ? C4 N2 C20 121.54(14) . . ? C3 N2 C20 117.10(13) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.261 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.040