Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Mikael Hakansson' 'Anders Lennartson' 'Tove Wiklund' _publ_contact_author_name 'Mikael Hakansson' _publ_contact_author_address ; Department of Chemistry Goteborg University Goteborg 412 96 SWEDEN ; _publ_contact_author_email HSON@CHEM.GU.SE _publ_requested_journal CrystEngComm _publ_section_title ; Concomitant polymorphs: chiral and racemic crystals of a diaryl sulphide ; data_alfa-1 _database_code_depnum_ccdc_archive 'CCDC 651277' _audit_creation_method shelxl-97 _chemical_name_systematic (10-nitro-phenantren-9-yl)(phenyl)sulphide _chemical_name_common none _chemical_melting_point 'not measured' _chemical_formula_moiety 'C20 H13 N O2 S' _chemical_formula_sum 'C20 H13 N O2 S' _chemical_formula_weight 331.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source c c 0.0033 0.0016 'international tables vol c tables 4.2.6.8 and 6.1.1.4' h h 0.0000 0.0000 'international tables vol c tables 4.2.6.8 and 6.1.1.4' n n 0.0061 0.0033 'international tables vol c tables 4.2.6.8 and 6.1.1.4' o o 0.0106 0.0060 'international tables vol c tables 4.2.6.8 and 6.1.1.4' s s 0.1246 0.1234 'international tables vol c tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_h-m 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_int_tables_number 19 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 5.8976(10) _cell_length_b 16.381(3) _cell_length_c 16.464(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1590.6(5) _cell_formula_units_z 4 _cell_measurement_temperature 303(2) _cell_measurement_reflns_used 2853 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 25.5 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_f_000 688 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_t_min 0.85 _exptl_absorpt_correction_t_max 0.97 _exptl_absorpt_process_details '(CrystalClear; Rigaku, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 303(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type mok\a _diffrn_radiation_wavelength 0.71073 _diffrn_source ; rotating-anode X-ray tube ; _diffrn_source_type 'Rigaku RU-H3R' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS IIc image-plate system' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 105 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10349 _diffrn_reflns_av_r_equivalents 0.0405 _diffrn_reflns_av_sigmai/neti 0.0281 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2853 _reflns_number_gt 2684 _reflns_threshold_expression >2sigma(i) _computing_data_collection '(CrystalClear; Rigaku, 2000)' _computing_cell_refinement '(CrystalClear; Rigaku, 2000)' _computing_data_reduction '(CrystalClear; Rigaku, 2000)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'shelxl-97 (sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 1990)' _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^)+(0.0529p)^2^+0.0438p] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'flack h d (1983), acta cryst. a39, 876-881' _refine_ls_abs_structure_flack 0.04(7) _refine_ls_number_reflns 2853 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_r_factor_all 0.0327 _refine_ls_r_factor_gt 0.0298 _refine_ls_wr_factor_ref 0.0793 _refine_ls_wr_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_s_all 1.051 _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 -0.0956(4) 0.13141(12) 0.89765(10) 0.0560(4) uani 1 1 d . . . c2 c -0.2686(4) 0.07555(15) 0.90743(12) 0.0681(6) uani 1 1 d . . . c3 c -0.2867(4) 0.00850(14) 0.85574(14) 0.0648(6) uani 1 1 d . . . c4 c -0.1313(3) -0.00339(11) 0.79522(12) 0.0534(4) uani 1 1 d . . . c5 c 0.0511(3) 0.05132(9) 0.78317(9) 0.0409(3) uani 1 1 d . . . c6 c 0.2185(3) 0.03959(9) 0.71986(9) 0.0396(3) uani 1 1 d . . . c7 c 0.2213(4) -0.03063(10) 0.67002(11) 0.0573(5) uani 1 1 d . . . c8 c 0.3882(5) -0.04256(12) 0.61284(11) 0.0680(6) uani 1 1 d . . . c9 c 0.5602(4) 0.01416(12) 0.60271(11) 0.0607(5) uani 1 1 d . . . c10 c 0.5632(3) 0.08352(11) 0.64900(10) 0.0497(4) uani 1 1 d . . . c11 c 0.3946(3) 0.09794(8) 0.70800(8) 0.0380(3) uani 1 1 d . . . c12 c 0.3999(3) 0.17024(8) 0.75861(8) 0.0385(3) uani 1 1 d . . . c13 c 0.2418(3) 0.17782(9) 0.81824(8) 0.0406(3) uani 1 1 d . . . c14 c 0.0661(3) 0.12056(9) 0.83488(9) 0.0412(3) uani 1 1 d . . . c15 c 0.5831(3) 0.29003(9) 0.65613(9) 0.0389(3) uani 1 1 d . . . c16 c 0.3930(3) 0.28136(9) 0.60726(10) 0.0428(3) uani 1 1 d . . . c17 c 0.3856(3) 0.32078(10) 0.53263(10) 0.0472(4) uani 1 1 d . . . c18 c 0.5634(3) 0.36980(11) 0.50761(10) 0.0521(4) uani 1 1 d . . . c19 c 0.7504(3) 0.37935(11) 0.55730(11) 0.0548(4) uani 1 1 d . . . c20 c 0.7623(3) 0.33944(10) 0.63099(10) 0.0487(4) uani 1 1 d . . . n1 n 0.2494(3) 0.25031(10) 0.87115(9) 0.0572(4) uani 1 1 d . . . o1 o 0.3504(3) 0.24455(11) 0.93488(9) 0.0923(5) uani 1 1 d . . . o2 o 0.1521(3) 0.31132(9) 0.84860(13) 0.0977(6) uani 1 1 d . . . s1 s 0.62130(7) 0.24294(3) 0.75250(2) 0.05217(14) uani 1 1 d . . . h1 h -0.080(4) 0.1797(15) 0.9320(15) 0.082(7) uiso 1 1 d . . . h2 h -0.383(5) 0.0882(16) 0.9506(17) 0.092(7) uiso 1 1 d . . . h3 h -0.424(5) -0.0216(14) 0.8674(14) 0.077(7) uiso 1 1 d . . . h4 h -0.151(4) -0.0510(14) 0.7570(13) 0.068(6) uiso 1 1 d . . . h7 h 0.110(5) -0.0705(17) 0.6770(15) 0.090(8) uiso 1 1 d . . . h8 h 0.375(6) -0.0896(18) 0.5834(17) 0.103(9) uiso 1 1 d . . . h9 h 0.688(4) 0.0030(16) 0.5593(17) 0.096(8) uiso 1 1 d . . . h10 h 0.686(4) 0.1205(14) 0.6431(13) 0.069(6) uiso 1 1 d . . . h16 h 0.267(3) 0.2416(13) 0.6232(11) 0.058(5) uiso 1 1 d . . . h17 h 0.252(4) 0.3136(12) 0.5009(11) 0.051(5) uiso 1 1 d . . . h18 h 0.549(3) 0.3950(12) 0.4547(12) 0.058(5) uiso 1 1 d . . . h19 h 0.870(4) 0.4145(15) 0.5403(14) 0.073(6) uiso 1 1 d . . . h20 h 0.900(3) 0.3456(10) 0.6649(11) 0.045(4) uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_u_11 _atom_site_aniso_u_22 _atom_site_aniso_u_33 _atom_site_aniso_u_23 _atom_site_aniso_u_13 _atom_site_aniso_u_12 c1 0.0651(11) 0.0624(10) 0.0406(7) 0.0110(8) 0.0055(9) 0.0223(9) c2 0.0587(11) 0.0875(15) 0.0580(11) 0.0398(11) 0.0171(10) 0.0208(10) c3 0.0533(11) 0.0680(13) 0.0732(12) 0.0377(11) -0.0023(10) 0.0018(9) c4 0.0560(10) 0.0450(8) 0.0591(9) 0.0194(8) -0.0080(9) -0.0014(8) c5 0.0490(9) 0.0349(7) 0.0390(7) 0.0109(6) -0.0078(7) 0.0038(6) c6 0.0527(8) 0.0305(7) 0.0357(7) 0.0051(5) -0.0074(7) 0.0045(6) c7 0.0834(13) 0.0344(8) 0.0540(10) -0.0013(7) -0.0067(10) -0.0010(8) c8 0.1077(16) 0.0467(9) 0.0496(10) -0.0107(8) 0.0011(12) 0.0166(12) c9 0.0813(14) 0.0560(10) 0.0447(9) 0.0003(8) 0.0108(10) 0.0206(9) c10 0.0591(11) 0.0513(10) 0.0387(8) 0.0069(7) 0.0023(7) 0.0080(8) c11 0.0480(8) 0.0354(7) 0.0306(6) 0.0052(5) -0.0045(6) 0.0044(6) c12 0.0467(7) 0.0345(7) 0.0342(6) 0.0055(5) -0.0091(7) 0.0018(6) c13 0.0531(8) 0.0338(7) 0.0349(7) -0.0019(5) -0.0092(7) 0.0088(6) c14 0.0499(8) 0.0405(8) 0.0332(6) 0.0092(6) -0.0023(6) 0.0094(6) c15 0.0392(7) 0.0351(7) 0.0425(7) -0.0026(5) -0.0027(6) -0.0010(6) c16 0.0420(8) 0.0380(7) 0.0484(8) 0.0037(6) -0.0062(7) -0.0033(6) c17 0.0545(9) 0.0433(8) 0.0438(8) 0.0007(6) -0.0100(8) 0.0037(7) c18 0.0659(11) 0.0481(9) 0.0424(8) 0.0042(7) 0.0097(8) 0.0065(8) c19 0.0505(9) 0.0536(10) 0.0601(10) 0.0034(8) 0.0163(9) -0.0060(8) c20 0.0411(8) 0.0502(9) 0.0548(9) -0.0036(7) 0.0020(8) -0.0059(7) n1 0.0703(9) 0.0443(7) 0.0571(8) -0.0137(6) -0.0065(7) 0.0082(7) o1 0.1299(14) 0.0919(11) 0.0550(7) -0.0329(8) -0.0261(9) 0.0141(12) o2 0.1107(13) 0.0462(8) 0.1361(15) -0.0243(9) -0.0277(13) 0.0255(9) s1 0.0549(2) 0.0532(2) 0.0485(2) 0.00830(18) -0.01896(19) -0.01340(18) _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 1.380(3) . ? c1 c14 1.417(2) . ? c1 h1 0.98(3) . ? c2 c3 1.394(4) . ? c2 h2 1.00(3) . ? c3 c4 1.368(3) . ? c3 h3 0.97(3) . ? c4 c5 1.414(2) . ? c4 h4 1.01(2) . ? c5 c14 1.421(2) . ? c5 c6 1.449(2) . ? c6 c7 1.413(2) . ? c6 c11 1.425(2) . ? c7 c8 1.376(3) . ? c7 h7 0.93(3) . ? c8 c9 1.386(3) . ? c8 h8 0.91(3) . ? c9 c10 1.368(3) . ? c9 h9 1.05(3) . ? c10 c11 1.410(2) . ? c10 h10 0.95(2) . ? c11 c12 1.448(2) . ? c12 c13 1.360(2) . ? c12 s1 1.7703(15) . ? c13 c14 1.424(2) . ? c13 n1 1.473(2) . ? c15 c16 1.387(2) . ? c15 c20 1.394(2) . ? c15 s1 1.7785(16) . ? c16 c17 1.389(2) . ? c16 h16 1.02(2) . ? c17 c18 1.383(3) . ? c17 h17 0.95(2) . ? c18 c19 1.382(3) . ? c18 h18 0.97(2) . ? c19 c20 1.380(3) . ? c19 h19 0.95(3) . ? c20 h20 0.99(2) . ? n1 o1 1.210(2) . ? n1 o2 1.211(2) . ? 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 c14 119.95(19) . . ? c2 c1 h1 122.6(15) . . ? c14 c1 h1 117.5(15) . . ? c1 c2 c3 120.54(19) . . ? c1 c2 h2 116.3(16) . . ? c3 c2 h2 123.0(16) . . ? c4 c3 c2 120.4(2) . . ? c4 c3 h3 129.2(15) . . ? c2 c3 h3 110.2(14) . . ? c3 c4 c5 121.44(19) . . ? c3 c4 h4 119.1(12) . . ? c5 c4 h4 119.4(12) . . ? c4 c5 c14 117.98(15) . . ? c4 c5 c6 122.38(15) . . ? c14 c5 c6 119.63(14) . . ? c7 c6 c11 117.27(15) . . ? c7 c6 c5 122.25(16) . . ? c11 c6 c5 120.43(13) . . ? c8 c7 c6 121.41(19) . . ? c8 c7 h7 119.3(16) . . ? c6 c7 h7 119.3(16) . . ? c7 c8 c9 120.73(17) . . ? c7 c8 h8 115(2) . . ? c9 c8 h8 124(2) . . ? c10 c9 c8 119.94(19) . . ? c10 c9 h9 120.9(14) . . ? c8 c9 h9 119.2(14) . . ? c9 c10 c11 120.90(18) . . ? c9 c10 h10 118.9(14) . . ? c11 c10 h10 120.1(14) . . ? c10 c11 c6 119.75(14) . . ? c10 c11 c12 121.19(15) . . ? c6 c11 c12 119.05(14) . . ? c13 c12 c11 118.38(14) . . ? c13 c12 s1 119.03(11) . . ? c11 c12 s1 122.24(12) . . ? c12 c13 c14 125.28(13) . . ? c12 c13 n1 118.67(15) . . ? c14 c13 n1 116.06(14) . . ? c1 c14 c5 119.67(16) . . ? c1 c14 c13 123.16(15) . . ? c5 c14 c13 117.12(13) . . ? c16 c15 c20 119.99(14) . . ? c16 c15 s1 125.13(12) . . ? c20 c15 s1 114.88(12) . . ? c15 c16 c17 119.40(15) . . ? c15 c16 h16 120.2(11) . . ? c17 c16 h16 120.0(11) . . ? c18 c17 c16 120.64(16) . . ? c18 c17 h17 122.4(11) . . ? c16 c17 h17 117.0(11) . . ? c19 c18 c17 119.61(15) . . ? c19 c18 h18 123.6(12) . . ? c17 c18 h18 116.8(12) . . ? c20 c19 c18 120.50(17) . . ? c20 c19 h19 120.5(14) . . ? c18 c19 h19 119.0(14) . . ? c19 c20 c15 119.84(16) . . ? c19 c20 h20 119.2(10) . . ? c15 c20 h20 120.9(10) . . ? o1 n1 o2 124.30(17) . . ? o1 n1 c13 117.69(15) . . ? o2 n1 c13 118.00(15) . . ? c12 s1 c15 104.42(7) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.121 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.026 _chemical_compound_source synthetic _exptl_crystal_recrystallization_method ; A solution in methylene chloride was layered with hexane at ambient temperature. ; _diffrn_ambient_pressure 101 # Attachment 'beta_1.cif' data_f2 _database_code_depnum_ccdc_archive 'CCDC 651278' _audit_creation_method SHELXL-97 _chemical_name_systematic (10-nitro-phenantren-9-yl)(phenyl)sulphide _chemical_name_common none _chemical_melting_point 'not measured' _chemical_formula_moiety 'C20 H13 N O2 S' _chemical_formula_sum 'C20 H13 N O2 S' _chemical_formula_weight 331.37 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 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 8.6557(15) _cell_length_b 12.706(2) _cell_length_c 14.439(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.420(7) _cell_angle_gamma 90.00 _cell_volume 1583.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 303(2) _cell_measurement_reflns_used 2836 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 25.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.823 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details '(CrystalClear; Rigaku, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 303(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'rotating-anode X-ray tube' _diffrn_source_type 'Rigaku RU-H3R' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS IIc image-plate system' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 105 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10089 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2836 _reflns_number_gt 2454 _reflns_threshold_expression >2sigma(I) _computing_data_collection '(CrystalClear; Rigaku, 2000)' _computing_cell_refinement '(CrystalClear; Rigaku, 2000)' _computing_data_reduction '(CrystalClear; Rigaku, 2000)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 1990)' _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^)+(0.0836P)^2^+0.0228P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2836 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.43610(19) 0.45726(12) -0.20571(10) 0.0517(4) Uani 1 1 d . . . C2 C 0.5594(2) 0.50752(13) -0.24037(11) 0.0608(4) Uani 1 1 d . . . C3 C 0.7041(2) 0.50571(13) -0.19138(12) 0.0637(4) Uani 1 1 d . . . C4 C 0.72568(18) 0.45489(12) -0.10773(11) 0.0541(4) Uani 1 1 d . . . C5 C 0.60206(15) 0.40236(10) -0.06868(9) 0.0421(3) Uani 1 1 d . . . C6 C 0.61932(15) 0.34921(10) 0.02098(9) 0.0426(3) Uani 1 1 d . . . C7 C 0.76293(18) 0.34398(12) 0.07408(11) 0.0531(4) Uani 1 1 d . . . C8 C 0.7769(2) 0.29691(13) 0.15946(12) 0.0619(4) Uani 1 1 d . . . C9 C 0.6479(2) 0.25303(12) 0.19656(13) 0.0614(4) Uani 1 1 d . . . C10 C 0.5057(2) 0.25548(11) 0.14709(11) 0.0538(4) Uani 1 1 d . . . C11 C 0.48856(16) 0.30241(10) 0.05845(9) 0.0429(3) Uani 1 1 d . . . C12 C 0.34086(15) 0.30310(10) 0.00404(9) 0.0433(3) Uani 1 1 d . . . C13 C 0.33126(15) 0.34973(11) -0.08038(9) 0.0429(3) Uani 1 1 d . . . C14 C 0.45563(15) 0.40363(10) -0.12014(9) 0.0421(3) Uani 1 1 d . . . C15 C 0.19012(15) 0.11807(12) 0.05590(9) 0.0463(3) Uani 1 1 d . . . C16 C 0.28680(19) 0.06065(15) 0.00252(13) 0.0626(4) Uani 1 1 d . . . C17 C 0.2902(2) -0.04788(15) 0.00999(16) 0.0759(6) Uani 1 1 d . . . C18 C 0.1976(2) -0.09981(15) 0.06865(15) 0.0742(5) Uani 1 1 d . . . C19 C 0.0998(2) -0.04307(14) 0.12034(12) 0.0657(5) Uani 1 1 d . . . C20 C 0.09613(18) 0.06585(13) 0.11474(10) 0.0532(4) Uani 1 1 d . . . O2 O 0.16119(17) 0.26929(13) -0.18981(10) 0.0834(4) Uani 1 1 d . . . O1 O 0.09277(14) 0.41869(12) -0.13409(11) 0.0848(4) Uani 1 1 d . . . S1 S 0.16788(4) 0.25677(3) 0.04901(3) 0.05407(18) Uani 1 1 d . . . N1 N 0.18233(14) 0.34546(11) -0.13841(9) 0.0563(3) Uani 1 1 d . . . H1 H 0.334(2) 0.4610(15) -0.2411(12) 0.066(5) Uiso 1 1 d . . . H2 H 0.542(2) 0.5436(15) -0.2979(14) 0.072(5) Uiso 1 1 d . . . H3 H 0.791(2) 0.5463(16) -0.2183(14) 0.081(6) Uiso 1 1 d . . . H4 H 0.824(2) 0.4522(16) -0.0746(13) 0.072(5) Uiso 1 1 d . . . H7 H 0.847(2) 0.3711(13) 0.0499(12) 0.062(5) Uiso 1 1 d . . . H8 H 0.869(2) 0.2953(17) 0.1950(13) 0.074(5) Uiso 1 1 d . . . H9 H 0.659(3) 0.2250(17) 0.2548(16) 0.077(6) Uiso 1 1 d . . . H10 H 0.413(3) 0.2254(16) 0.1748(14) 0.075(6) Uiso 1 1 d . . . H16 H 0.349(3) 0.0990(18) -0.0416(14) 0.085(6) Uiso 1 1 d . . . H17 H 0.361(3) -0.0797(19) -0.0302(15) 0.092(7) Uiso 1 1 d . . . H18 H 0.202(3) -0.175(2) 0.0777(16) 0.098(7) Uiso 1 1 d . . . H19 H 0.021(3) -0.0762(18) 0.1631(16) 0.098(7) Uiso 1 1 d . . . H20 H 0.030(2) 0.1062(15) 0.1515(12) 0.066(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0542(9) 0.0530(8) 0.0481(7) -0.0019(6) 0.0052(6) 0.0039(7) C2 0.0742(11) 0.0575(9) 0.0524(8) 0.0031(7) 0.0158(8) -0.0003(7) C3 0.0649(10) 0.0621(10) 0.0674(9) -0.0039(7) 0.0264(8) -0.0111(8) C4 0.0416(8) 0.0587(9) 0.0632(8) -0.0084(7) 0.0120(6) -0.0040(6) C5 0.0363(7) 0.0412(7) 0.0496(7) -0.0074(5) 0.0079(5) 0.0034(5) C6 0.0374(7) 0.0391(6) 0.0509(7) -0.0077(5) 0.0010(5) 0.0063(5) C7 0.0400(8) 0.0516(8) 0.0667(9) -0.0072(7) -0.0025(7) 0.0062(6) C8 0.0566(10) 0.0562(9) 0.0688(10) -0.0075(8) -0.0203(8) 0.0120(7) C9 0.0743(12) 0.0513(9) 0.0558(9) 0.0036(7) -0.0130(8) 0.0058(7) C10 0.0608(10) 0.0483(8) 0.0517(8) 0.0025(6) 0.0008(7) 0.0014(6) C11 0.0422(7) 0.0393(7) 0.0469(7) -0.0038(5) 0.0020(6) 0.0054(5) C12 0.0370(7) 0.0426(7) 0.0508(7) -0.0030(5) 0.0065(5) 0.0018(5) C13 0.0330(6) 0.0466(7) 0.0487(7) -0.0048(6) 0.0008(5) 0.0034(5) C14 0.0386(7) 0.0420(7) 0.0462(6) -0.0056(5) 0.0058(5) 0.0034(5) C15 0.0362(7) 0.0517(7) 0.0501(7) -0.0051(6) -0.0029(5) -0.0030(5) C16 0.0475(9) 0.0650(10) 0.0761(10) -0.0170(8) 0.0111(8) -0.0028(7) C17 0.0576(11) 0.0633(11) 0.1057(14) -0.0307(10) -0.0009(10) 0.0066(8) C18 0.0691(12) 0.0522(9) 0.0974(13) -0.0090(9) -0.0188(10) -0.0033(8) C19 0.0696(11) 0.0593(10) 0.0661(10) 0.0049(8) -0.0087(8) -0.0128(8) C20 0.0505(8) 0.0580(8) 0.0506(7) -0.0016(6) 0.0002(6) -0.0041(7) O2 0.0729(10) 0.0931(10) 0.0800(9) -0.0152(7) -0.0213(7) -0.0129(7) O1 0.0438(7) 0.0977(10) 0.1118(10) 0.0116(8) -0.0019(6) 0.0208(6) S1 0.0410(3) 0.0524(3) 0.0709(3) 0.00210(15) 0.01778(18) 0.00286(14) N1 0.0394(7) 0.0679(8) 0.0609(7) 0.0053(6) -0.0013(5) -0.0013(6) _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 1.371(2) . ? C1 C14 1.410(2) . ? C1 H1 0.99(2) . ? C2 C3 1.390(3) . ? C2 H2 0.95(2) . ? C3 C4 1.370(3) . ? C3 H3 1.01(2) . ? C4 C5 1.415(2) . ? C4 H4 0.94(2) . ? C5 C14 1.4190(18) . ? C5 C6 1.4577(19) . ? C6 C7 1.4108(19) . ? C6 C11 1.422(2) . ? C7 C8 1.367(3) . ? C7 H7 0.902(19) . ? C8 C9 1.392(3) . ? C8 H8 0.91(2) . ? C9 C10 1.375(3) . ? C9 H9 0.91(2) . ? C10 C11 1.409(2) . ? C10 H10 1.00(2) . ? C11 C12 1.4481(18) . ? C12 C13 1.352(2) . ? C12 S1 1.7776(14) . ? C13 C14 1.4328(19) . ? C13 N1 1.4833(17) . ? C15 C16 1.388(2) . ? C15 C20 1.389(2) . ? C15 S1 1.7748(15) . ? C16 C17 1.383(3) . ? C16 H16 1.00(2) . ? C17 C18 1.378(3) . ? C17 H17 0.96(2) . ? C18 C19 1.375(3) . ? C18 H18 0.97(2) . ? C19 C20 1.387(2) . ? C19 H19 1.04(2) . ? C20 H20 0.957(19) . ? O2 N1 1.2248(19) . ? O1 N1 1.2158(18) . ? 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 C14 120.05(15) . . ? C2 C1 H1 118.7(10) . . ? C14 C1 H1 121.2(10) . . ? C1 C2 C3 120.18(15) . . ? C1 C2 H2 117.9(13) . . ? C3 C2 H2 122.0(13) . . ? C4 C3 C2 120.85(15) . . ? C4 C3 H3 121.6(12) . . ? C2 C3 H3 117.5(12) . . ? C3 C4 C5 121.19(16) . . ? C3 C4 H4 121.4(12) . . ? C5 C4 H4 117.4(12) . . ? C4 C5 C14 117.29(13) . . ? C4 C5 C6 122.94(13) . . ? C14 C5 C6 119.77(12) . . ? C7 C6 C11 117.87(13) . . ? C7 C6 C5 122.01(13) . . ? C11 C6 C5 120.11(12) . . ? C8 C7 C6 121.56(16) . . ? C8 C7 H7 119.9(11) . . ? C6 C7 H7 118.5(11) . . ? C7 C8 C9 120.33(15) . . ? C7 C8 H8 121.9(13) . . ? C9 C8 H8 117.7(13) . . ? C10 C9 C8 120.22(16) . . ? C10 C9 H9 120.8(14) . . ? C8 C9 H9 119.0(14) . . ? C9 C10 C11 120.59(17) . . ? C9 C10 H10 119.9(12) . . ? C11 C10 H10 119.5(12) . . ? C10 C11 C6 119.42(13) . . ? C10 C11 C12 121.47(13) . . ? C6 C11 C12 119.10(12) . . ? C13 C12 C11 118.82(12) . . ? C13 C12 S1 118.65(11) . . ? C11 C12 S1 122.21(10) . . ? C12 C13 C14 125.09(12) . . ? C12 C13 N1 118.92(12) . . ? C14 C13 N1 115.99(11) . . ? C1 C14 C5 120.42(13) . . ? C1 C14 C13 122.63(13) . . ? C5 C14 C13 116.95(12) . . ? C16 C15 C20 119.67(15) . . ? C16 C15 S1 123.94(12) . . ? C20 C15 S1 116.26(11) . . ? C17 C16 C15 119.40(18) . . ? C17 C16 H16 121.9(13) . . ? C15 C16 H16 118.6(13) . . ? C18 C17 C16 121.01(18) . . ? C18 C17 H17 126.5(14) . . ? C16 C17 H17 112.5(14) . . ? C19 C18 C17 119.61(18) . . ? C19 C18 H18 117.6(14) . . ? C17 C18 H18 122.7(14) . . ? C18 C19 C20 120.28(18) . . ? C18 C19 H19 124.6(13) . . ? C20 C19 H19 115.1(13) . . ? C19 C20 C15 120.02(16) . . ? C19 C20 H20 120.9(11) . . ? C15 C20 H20 119.1(11) . . ? C15 S1 C12 104.98(6) . . ? O1 N1 O2 124.74(14) . . ? O1 N1 C13 118.22(13) . . ? O2 N1 C13 117.00(13) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.174 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.034 _chemical_compound_source synthetic _exptl_crystal_recrystallization_method ; A solution in methylene chloride was layered with hexane at ambient temperature. ; _diffrn_ambient_pressure 101