# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Harkesh B. Singh' 'R. Butcher' 'Karuppasamy Kandasamy' 'Sangit Kumar' _publ_contact_author_name 'Prof Harkesh B. Singh' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology, Bombay Powai Mumbai Maharashtra 400076 INDIA ; _publ_contact_author_email CHHBSIA@CHEM.IITB.AC.IN _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Synthesis of organochalcogens stabilized by intramolecular nonbonded interaction of sterically non-hindered 2-phenyl-2-oxazoline: Self-organization of organylselenenyl halides by Se...Se interaction ; data_6 _database_code_depnum_ccdc_archive 'CCDC 229425' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 N O Se' _chemical_formula_weight 225.12 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.893(2) _cell_length_b 7.901(2) _cell_length_c 15.805(5) _cell_angle_alpha 85.564(5) _cell_angle_beta 84.968(5) _cell_angle_gamma 62.449(5) _cell_volume 869.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description chunk _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.719 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 4.263 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.6253 _exptl_absorpt_correction_T_max 1.000 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8279 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 27.00 _reflns_number_total 8283 _reflns_number_gt 6332 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1309P)^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_number_reflns 8283 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0904 _refine_ls_R_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.1870 _refine_ls_wR_factor_gt 0.1774 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 Se1A Se 0.22800(10) 0.19463(10) 0.15657(4) 0.03763(19) Uani 1 1 d . . . Se1B Se 0.22666(10) 0.15889(11) 0.30514(5) 0.0413(2) Uani 1 1 d . . . O1A O 0.2383(8) 0.0351(8) -0.1113(3) 0.0568(14) Uani 1 1 d . . . O1B O -0.0762(10) 0.2875(11) 0.5661(4) 0.081(2) Uani 1 1 d . . . N1A N 0.2497(9) 0.2254(8) -0.0159(4) 0.0465(15) Uani 1 1 d . . . N1B N 0.1868(10) 0.1973(10) 0.4789(4) 0.0544(17) Uani 1 1 d . . . C1A C 0.2457(8) -0.0431(9) 0.1221(4) 0.0337(14) Uani 1 1 d . . . C2A C 0.2538(9) -0.1847(9) 0.1822(5) 0.0381(16) Uani 1 1 d . . . H2AA H 0.2504 -0.1654 0.2398 0.046 Uiso 1 1 calc R . . C3A C 0.2670(11) -0.3536(11) 0.1566(6) 0.052(2) Uani 1 1 d . . . H3AA H 0.2712 -0.4474 0.1969 0.062 Uiso 1 1 calc R . . C4A C 0.2739(12) -0.3836(12) 0.0712(5) 0.059(2) Uani 1 1 d . . . H4AA H 0.2849 -0.4985 0.0542 0.071 Uiso 1 1 calc R . . C5A C 0.2646(11) -0.2444(11) 0.0110(5) 0.0461(19) Uani 1 1 d . . . H5AA H 0.2670 -0.2645 -0.0464 0.055 Uiso 1 1 calc R . . C6A C 0.2517(9) -0.0733(9) 0.0360(4) 0.0349(15) Uani 1 1 d . . . C7A C 0.2488(10) 0.0698(11) -0.0278(5) 0.0432(18) Uani 1 1 d . . . C8A C 0.2368(10) 0.2048(12) -0.1611(5) 0.049(2) Uani 1 1 d . . . H8AA H 0.3491 0.1664 -0.2001 0.059 Uiso 1 1 calc R . . H8AB H 0.1233 0.2690 -0.1935 0.059 Uiso 1 1 calc R . . C9A C 0.2374(11) 0.3298(11) -0.0981(4) 0.0541(18) Uani 1 1 d . . . H9AA H 0.1210 0.4502 -0.0988 0.065 Uiso 1 1 calc R . . H9AB H 0.3463 0.3555 -0.1093 0.065 Uiso 1 1 calc R . . C1B C -0.0366(9) 0.2152(10) 0.3345(4) 0.0377(15) Uani 1 1 d . . . C2B C -0.1591(11) 0.2283(12) 0.2747(5) 0.0495(19) Uani 1 1 d . . . H2BA H -0.1137 0.2107 0.2182 0.059 Uiso 1 1 calc R . . C3B C -0.3472(11) 0.2665(13) 0.2952(6) 0.056(2) Uani 1 1 d . . . H3BA H -0.4256 0.2705 0.2536 0.068 Uiso 1 1 calc R . . C4B C -0.4171(12) 0.2993(15) 0.3811(6) 0.072(3) Uani 1 1 d . . . H4BA H -0.5440 0.3292 0.3963 0.086 Uiso 1 1 calc R . . C5B C -0.2995(11) 0.2873(13) 0.4411(6) 0.056(2) Uani 1 1 d . . . H5BA H -0.3466 0.3048 0.4975 0.067 Uiso 1 1 calc R . . C6B C -0.1065(10) 0.2488(10) 0.4208(5) 0.0406(16) Uani 1 1 d . . . C7B C 0.0138(11) 0.2392(11) 0.4876(5) 0.0458(18) Uani 1 1 d . . . C8B C 0.2511(13) 0.2133(14) 0.5611(5) 0.064(2) Uani 1 1 d . . . H8BA H 0.2913 0.3127 0.5582 0.077 Uiso 1 1 calc R . . H8BB H 0.3556 0.0933 0.5795 0.077 Uiso 1 1 calc R . . C9B C 0.0701(14) 0.2657(14) 0.6203(5) 0.068(2) Uani 1 1 d . . . H9BA H 0.0907 0.1651 0.6635 0.082 Uiso 1 1 calc R . . H9BB H 0.0348 0.3837 0.6480 0.082 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 Se1A 0.0461(4) 0.0355(4) 0.0370(4) -0.0029(3) -0.0005(3) -0.0236(3) Se1B 0.0373(4) 0.0542(5) 0.0381(4) -0.0060(3) -0.0030(3) -0.0251(3) O1A 0.062(3) 0.079(4) 0.033(3) -0.010(3) 0.000(2) -0.034(3) O1B 0.080(4) 0.118(6) 0.045(4) -0.031(4) 0.020(3) -0.046(4) N1A 0.062(4) 0.038(3) 0.039(3) -0.001(3) 0.000(3) -0.023(3) N1B 0.069(4) 0.077(5) 0.032(3) -0.006(3) -0.007(3) -0.045(4) C1A 0.022(3) 0.031(3) 0.051(4) -0.007(3) 0.002(3) -0.015(2) C2A 0.043(4) 0.034(4) 0.041(4) 0.003(3) -0.004(3) -0.021(3) C3A 0.053(4) 0.041(4) 0.063(6) 0.010(4) 0.003(4) -0.025(3) C4A 0.068(6) 0.054(5) 0.064(6) -0.027(4) 0.020(4) -0.035(4) C5A 0.046(4) 0.043(4) 0.056(5) -0.016(3) 0.009(3) -0.025(3) C6A 0.031(3) 0.033(3) 0.042(4) -0.002(3) -0.003(3) -0.016(3) C7A 0.033(4) 0.057(5) 0.037(4) -0.009(3) 0.002(3) -0.018(3) C8A 0.039(4) 0.067(5) 0.042(4) 0.013(4) -0.012(3) -0.025(4) C9A 0.046(4) 0.056(5) 0.051(4) 0.007(4) -0.009(4) -0.016(3) C1B 0.038(4) 0.044(4) 0.037(4) -0.003(3) 0.002(3) -0.025(3) C2B 0.042(4) 0.067(5) 0.045(5) -0.007(4) -0.005(3) -0.029(4) C3B 0.034(4) 0.079(6) 0.062(6) -0.007(4) -0.003(4) -0.030(4) C4B 0.042(5) 0.109(8) 0.073(6) -0.026(6) 0.008(4) -0.041(5) C5B 0.048(4) 0.071(5) 0.053(5) -0.019(4) 0.018(4) -0.032(4) C6B 0.039(4) 0.041(4) 0.047(4) -0.010(3) 0.005(3) -0.023(3) C7B 0.053(5) 0.053(4) 0.035(4) -0.012(3) 0.006(3) -0.027(4) C8B 0.086(6) 0.076(6) 0.044(5) -0.010(4) -0.012(4) -0.047(5) C9B 0.101(7) 0.072(6) 0.040(4) -0.016(4) -0.008(5) -0.043(5) _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 Se1A C1A 1.935(6) . ? Se1A Se1B 2.3429(10) . ? Se1B C1B 1.934(7) . ? O1A C7A 1.386(9) . ? O1A C8A 1.497(9) . ? O1B C7B 1.362(9) . ? O1B C9B 1.436(11) . ? N1A C7A 1.261(10) . ? N1A C9A 1.470(9) . ? N1B C7B 1.244(10) . ? N1B C8B 1.471(9) . ? C1A C2A 1.392(9) . ? C1A C6A 1.393(10) . ? C2A C3A 1.380(11) . ? C3A C4A 1.380(12) . ? C4A C5A 1.376(11) . ? C5A C6A 1.393(9) . ? C6A C7A 1.449(10) . ? C8A C9A 1.457(11) . ? C1B C2B 1.375(10) . ? C1B C6B 1.423(10) . ? C2B C3B 1.384(11) . ? C3B C4B 1.417(12) . ? C4B C5B 1.352(12) . ? C5B C6B 1.420(10) . ? C6B C7B 1.456(10) . ? C8B C9B 1.538(13) . ? 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 C1A Se1A Se1B 103.5(2) . . ? C1B Se1B Se1A 101.4(2) . . ? C7A O1A C8A 104.2(6) . . ? C7B O1B C9B 105.3(7) . . ? C7A N1A C9A 108.9(7) . . ? C7B N1B C8B 108.8(7) . . ? C2A C1A C6A 119.6(6) . . ? C2A C1A Se1A 120.9(5) . . ? C6A C1A Se1A 119.5(5) . . ? C3A C2A C1A 120.2(7) . . ? C2A C3A C4A 120.1(7) . . ? C5A C4A C3A 120.4(7) . . ? C4A C5A C6A 120.1(8) . . ? C1A C6A C5A 119.7(6) . . ? C1A C6A C7A 120.6(6) . . ? C5A C6A C7A 119.8(7) . . ? N1A C7A O1A 116.0(7) . . ? N1A C7A C6A 127.4(7) . . ? O1A C7A C6A 116.6(7) . . ? C9A C8A O1A 105.4(6) . . ? C8A C9A N1A 105.4(7) . . ? C2B C1B C6B 119.1(6) . . ? C2B C1B Se1B 122.4(5) . . ? C6B C1B Se1B 118.5(5) . . ? C1B C2B C3B 122.9(8) . . ? C2B C3B C4B 118.2(8) . . ? C5B C4B C3B 120.1(7) . . ? C4B C5B C6B 122.1(8) . . ? C5B C6B C1B 117.6(7) . . ? C5B C6B C7B 120.1(7) . . ? C1B C6B C7B 122.3(6) . . ? N1B C7B O1B 118.0(7) . . ? N1B C7B C6B 126.3(7) . . ? O1B C7B C6B 115.7(7) . . ? N1B C8B C9B 102.4(7) . . ? O1B C9B C8B 105.3(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 C1A Se1A Se1B C1B -79.5(3) . . . . ? Se1B Se1A C1A C2A 0.1(5) . . . . ? Se1B Se1A C1A C6A -179.4(4) . . . . ? C6A C1A C2A C3A -0.3(10) . . . . ? Se1A C1A C2A C3A -179.8(5) . . . . ? C1A C2A C3A C4A 0.6(11) . . . . ? C2A C3A C4A C5A -1.1(12) . . . . ? C3A C4A C5A C6A 1.2(12) . . . . ? C2A C1A C6A C5A 0.4(9) . . . . ? Se1A C1A C6A C5A 179.9(5) . . . . ? C2A C1A C6A C7A -178.3(6) . . . . ? Se1A C1A C6A C7A 1.3(8) . . . . ? C4A C5A C6A C1A -0.9(11) . . . . ? C4A C5A C6A C7A 177.8(7) . . . . ? C9A N1A C7A O1A 0.4(9) . . . . ? C9A N1A C7A C6A -177.6(6) . . . . ? C8A O1A C7A N1A 1.5(8) . . . . ? C8A O1A C7A C6A 179.7(5) . . . . ? C1A C6A C7A N1A 3.5(11) . . . . ? C5A C6A C7A N1A -175.2(7) . . . . ? C1A C6A C7A O1A -174.5(5) . . . . ? C5A C6A C7A O1A 6.8(9) . . . . ? C7A O1A C8A C9A -2.8(7) . . . . ? O1A C8A C9A N1A 3.0(8) . . . . ? C7A N1A C9A C8A -2.2(9) . . . . ? Se1A Se1B C1B C2B 11.7(7) . . . . ? Se1A Se1B C1B C6B -166.6(5) . . . . ? C6B C1B C2B C3B -2.3(12) . . . . ? Se1B C1B C2B C3B 179.3(7) . . . . ? C1B C2B C3B C4B 2.1(13) . . . . ? C2B C3B C4B C5B -2.0(15) . . . . ? C3B C4B C5B C6B 2.3(15) . . . . ? C4B C5B C6B C1B -2.4(12) . . . . ? C4B C5B C6B C7B 179.4(9) . . . . ? C2B C1B C6B C5B 2.4(11) . . . . ? Se1B C1B C6B C5B -179.2(6) . . . . ? C2B C1B C6B C7B -179.5(7) . . . . ? Se1B C1B C6B C7B -1.0(9) . . . . ? C8B N1B C7B O1B -0.3(11) . . . . ? C8B N1B C7B C6B 177.3(8) . . . . ? C9B O1B C7B N1B -2.6(11) . . . . ? C9B O1B C7B C6B 179.5(7) . . . . ? C5B C6B C7B N1B 176.1(8) . . . . ? C1B C6B C7B N1B -2.0(13) . . . . ? C5B C6B C7B O1B -6.2(11) . . . . ? C1B C6B C7B O1B 175.7(7) . . . . ? C7B N1B C8B C9B 2.8(9) . . . . ? C7B O1B C9B C8B 4.1(9) . . . . ? N1B C8B C9B O1B -4.2(9) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.177 _refine_diff_density_min -1.028 _refine_diff_density_rms 0.197 #=== END data_11 _database_code_depnum_ccdc_archive 'CCDC 229426' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N2 O2 S2' _chemical_formula_weight 356.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7728(7) _cell_length_b 7.7691(6) _cell_length_c 15.5568(13) _cell_angle_alpha 85.376(5) _cell_angle_beta 85.840(7) _cell_angle_gamma 63.251(7) _cell_volume 835.48(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 51 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 28.02 _exptl_crystal_description thick_plate _exptl_crystal_colour Pale_yellow _exptl_crystal_size_max 0.99 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 2.998 _exptl_absorpt_correction_type Shelxa _exptl_absorpt_correction_T_min 0.5842 _exptl_absorpt_correction_T_max 0.8743 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2434 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0106 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 57.48 _reflns_number_total 2243 _reflns_number_gt 2184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0260P)^2^+0.6710P] 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 SHELXL _refine_ls_extinction_coef 0.025(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2243 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0827 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 S1A S 0.68930(8) 0.71975(8) 0.66528(3) 0.0325(2) Uani 1 1 d . . . S1B S 0.67038(9) 0.70896(8) 0.79787(4) 0.0346(2) Uani 1 1 d . . . O1A O 0.5283(3) 0.7460(3) 0.39500(11) 0.0536(5) Uani 1 1 d . . . O1B O 0.7790(3) 0.4314(3) 1.06275(11) 0.0644(6) Uani 1 1 d . . . N1A N 0.7325(3) 0.7435(3) 0.49002(12) 0.0394(5) Uani 1 1 d . . . N1B N 0.7064(4) 0.6932(3) 0.97356(13) 0.0489(6) Uani 1 1 d . . . C1A C 0.4622(3) 0.7447(3) 0.63307(14) 0.0278(5) Uani 1 1 d . . . C2A C 0.3192(3) 0.7514(3) 0.69316(16) 0.0362(6) Uani 1 1 d . . . H2AA H 0.3402 0.7448 0.7517 0.043(7) Uiso 1 1 calc R . . C3A C 0.1457(4) 0.7676(4) 0.66744(18) 0.0437(7) Uani 1 1 d . . . H3AA H 0.0511 0.7728 0.7088 0.043(7) Uiso 1 1 calc R . . C4A C 0.1119(4) 0.7763(4) 0.58107(18) 0.0473(7) Uani 1 1 d . . . H4AA H -0.0047 0.7866 0.5639 0.057(8) Uiso 1 1 calc R . . C5A C 0.2524(4) 0.7694(4) 0.52073(17) 0.0417(6) Uani 1 1 d . . . H5AA H 0.2294 0.7755 0.4625 0.054(8) Uiso 1 1 calc R . . C6A C 0.4285(3) 0.7536(3) 0.54450(14) 0.0304(5) Uani 1 1 d . . . C7A C 0.5730(3) 0.7477(3) 0.47750(14) 0.0317(6) Uani 1 1 d . . . C8A C 0.8319(4) 0.7345(4) 0.40517(15) 0.0447(7) Uani 1 1 d . . . H8AA H 0.9501 0.6152 0.4014 0.058(8) Uiso 1 1 calc R . . H8AB H 0.8624 0.8426 0.3944 0.055(8) Uiso 1 1 calc R . . C9A C 0.6890(4) 0.7435(4) 0.34193(16) 0.0502(7) Uani 1 1 d . . . H9AA H 0.6492 0.8593 0.3042 0.058(8) Uiso 1 1 calc R . . H9AB H 0.7446 0.6317 0.3070 0.059(8) Uiso 1 1 calc R . . C1B C 0.7182(3) 0.4646(3) 0.82784(14) 0.0311(5) Uani 1 1 d . . . C2B C 0.7243(4) 0.3401(3) 0.76679(16) 0.0390(6) Uani 1 1 d . . . H2BA H 0.7044 0.3841 0.7093 0.039(7) Uiso 1 1 calc R . . C3B C 0.7594(4) 0.1522(4) 0.79041(18) 0.0498(7) Uani 1 1 d . . . H3BA H 0.7624 0.0714 0.7487 0.054(8) Uiso 1 1 calc R . . C4B C 0.7898(5) 0.0840(4) 0.87487(19) 0.0557(8) Uani 1 1 d . . . H4BA H 0.8158 -0.0433 0.8903 0.076(10) Uiso 1 1 calc R . . C5B C 0.7815(4) 0.2053(4) 0.93653(18) 0.0487(7) Uani 1 1 d . . . H5BA H 0.8001 0.1593 0.9939 0.059(8) Uiso 1 1 calc R . . C6B C 0.7457(3) 0.3965(3) 0.91469(15) 0.0344(6) Uani 1 1 d . . . C7B C 0.7409(3) 0.5185(4) 0.98287(14) 0.0365(6) Uani 1 1 d . . . C8B C 0.7224(5) 0.7547(4) 1.05836(16) 0.0517(7) Uani 1 1 d . . . H8BA H 0.6032 0.8632 1.0759 0.063(9) Uiso 1 1 calc R . . H8BB H 0.8267 0.7912 1.0572 0.051(8) Uiso 1 1 calc R . . C9B C 0.7638(5) 0.5779(5) 1.11871(17) 0.0560(8) Uani 1 1 d . . . H9BA H 0.8831 0.5384 1.1477 0.073(10) Uiso 1 1 calc R . . H9BB H 0.6597 0.6036 1.1618 0.061(9) 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 S1A 0.0361(4) 0.0398(4) 0.0260(3) 0.0033(2) -0.0075(2) -0.0209(3) S1B 0.0519(4) 0.0311(3) 0.0260(3) 0.0014(2) -0.0094(2) -0.0225(3) O1A 0.0713(13) 0.0726(13) 0.0269(10) -0.0014(8) -0.0129(9) -0.0396(11) O1B 0.1063(17) 0.0584(13) 0.0293(10) 0.0107(9) -0.0218(10) -0.0368(12) N1A 0.0414(12) 0.0505(13) 0.0281(11) -0.0007(9) -0.0022(9) -0.0223(10) N1B 0.0784(17) 0.0490(14) 0.0290(12) -0.0007(10) -0.0099(11) -0.0361(12) C1A 0.0316(12) 0.0197(11) 0.0309(12) 0.0013(9) -0.0071(10) -0.0099(9) C2A 0.0406(14) 0.0325(13) 0.0347(14) 0.0028(10) -0.0045(11) -0.0158(11) C3A 0.0333(14) 0.0388(14) 0.0574(18) 0.0066(12) -0.0010(12) -0.0162(12) C4A 0.0373(15) 0.0469(16) 0.0619(19) 0.0110(13) -0.0184(13) -0.0224(13) C5A 0.0468(16) 0.0408(14) 0.0419(15) 0.0058(11) -0.0200(12) -0.0220(12) C6A 0.0364(13) 0.0224(11) 0.0327(13) 0.0031(9) -0.0102(10) -0.0128(10) C7A 0.0468(15) 0.0201(11) 0.0266(12) -0.0002(9) -0.0100(10) -0.0125(10) C8A 0.0533(17) 0.0408(15) 0.0331(14) -0.0034(11) 0.0079(12) -0.0160(13) C9A 0.080(2) 0.0414(15) 0.0269(13) -0.0035(11) 0.0014(13) -0.0255(15) C1B 0.0331(13) 0.0278(12) 0.0323(13) 0.0001(10) -0.0066(10) -0.0130(10) C2B 0.0502(15) 0.0314(13) 0.0340(14) -0.0029(10) -0.0083(11) -0.0159(12) C3B 0.0640(18) 0.0310(14) 0.0537(18) -0.0069(12) -0.0114(14) -0.0187(13) C4B 0.075(2) 0.0296(14) 0.064(2) 0.0059(13) -0.0170(15) -0.0240(14) C5B 0.0623(18) 0.0410(15) 0.0437(16) 0.0142(12) -0.0163(13) -0.0245(13) C6B 0.0379(13) 0.0359(13) 0.0315(13) 0.0036(10) -0.0095(10) -0.0180(11) C7B 0.0396(14) 0.0474(16) 0.0251(13) 0.0045(11) -0.0075(10) -0.0220(12) C8B 0.0644(19) 0.0677(19) 0.0333(15) -0.0100(13) -0.0058(13) -0.0368(17) C9B 0.066(2) 0.078(2) 0.0285(14) -0.0043(14) -0.0093(13) -0.0353(17) _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 S1A C1A 1.792(2) . ? S1A S1B 2.0549(8) . ? S1B C1B 1.791(2) . ? O1A C7A 1.356(3) . ? O1A C9A 1.440(3) . ? O1B C7B 1.352(3) . ? O1B C9B 1.446(3) . ? N1A C7A 1.254(3) . ? N1A C8A 1.471(3) . ? N1B C7B 1.258(3) . ? N1B C8B 1.471(3) . ? C1A C2A 1.385(3) . ? C1A C6A 1.412(3) . ? C2A C3A 1.382(3) . ? C3A C4A 1.378(4) . ? C4A C5A 1.372(4) . ? C5A C6A 1.393(3) . ? C6A C7A 1.463(3) . ? C8A C9A 1.511(4) . ? C1B C2B 1.393(3) . ? C1B C6B 1.406(3) . ? C2B C3B 1.382(3) . ? C3B C4B 1.372(4) . ? C4B C5B 1.377(4) . ? C5B C6B 1.400(3) . ? C6B C7B 1.466(3) . ? C8B C9B 1.520(4) . ? 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 C1A S1A S1B 105.11(8) . . ? C1B S1B S1A 104.31(8) . . ? C7A O1A C9A 105.7(2) . . ? C7B O1B C9B 106.0(2) . . ? C7A N1A C8A 107.2(2) . . ? C7B N1B C8B 107.5(2) . . ? C2A C1A C6A 118.8(2) . . ? C2A C1A S1A 121.57(17) . . ? C6A C1A S1A 119.61(17) . . ? C3A C2A C1A 121.0(2) . . ? C4A C3A C2A 120.5(2) . . ? C5A C4A C3A 119.2(2) . . ? C4A C5A C6A 121.7(2) . . ? C5A C6A C1A 118.8(2) . . ? C5A C6A C7A 119.5(2) . . ? C1A C6A C7A 121.7(2) . . ? N1A C7A O1A 118.1(2) . . ? N1A C7A C6A 125.8(2) . . ? O1A C7A C6A 116.2(2) . . ? N1A C8A C9A 104.2(2) . . ? O1A C9A C8A 104.72(19) . . ? C2B C1B C6B 118.7(2) . . ? C2B C1B S1B 121.25(18) . . ? C6B C1B S1B 120.03(17) . . ? C3B C2B C1B 121.0(2) . . ? C4B C3B C2B 120.5(2) . . ? C3B C4B C5B 119.5(2) . . ? C4B C5B C6B 121.3(2) . . ? C5B C6B C1B 118.9(2) . . ? C5B C6B C7B 119.0(2) . . ? C1B C6B C7B 122.1(2) . . ? N1B C7B O1B 118.0(2) . . ? N1B C7B C6B 126.3(2) . . ? O1B C7B C6B 115.7(2) . . ? N1B C8B C9B 104.1(2) . . ? O1B C9B C8B 104.3(2) . . ? 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 C1A S1A S1B C1B 80.41(11) . . . . ? S1B S1A C1A C2A -0.51(19) . . . . ? S1B S1A C1A C6A -179.04(15) . . . . ? C6A C1A C2A C3A -0.4(3) . . . . ? S1A C1A C2A C3A -178.96(18) . . . . ? C1A C2A C3A C4A 0.4(4) . . . . ? C2A C3A C4A C5A -0.3(4) . . . . ? C3A C4A C5A C6A 0.1(4) . . . . ? C4A C5A C6A C1A -0.1(3) . . . . ? C4A C5A C6A C7A -179.7(2) . . . . ? C2A C1A C6A C5A 0.3(3) . . . . ? S1A C1A C6A C5A 178.82(17) . . . . ? C2A C1A C6A C7A 179.87(19) . . . . ? S1A C1A C6A C7A -1.6(3) . . . . ? C8A N1A C7A O1A -0.9(3) . . . . ? C8A N1A C7A C6A 178.9(2) . . . . ? C9A O1A C7A N1A -1.2(3) . . . . ? C9A O1A C7A C6A 179.04(19) . . . . ? C5A C6A C7A N1A 176.2(2) . . . . ? C1A C6A C7A N1A -3.4(3) . . . . ? C5A C6A C7A O1A -4.1(3) . . . . ? C1A C6A C7A O1A 176.31(19) . . . . ? C7A N1A C8A C9A 2.4(3) . . . . ? C7A O1A C9A C8A 2.6(3) . . . . ? N1A C8A C9A O1A -3.1(3) . . . . ? S1A S1B C1B C2B -11.1(2) . . . . ? S1A S1B C1B C6B 170.51(17) . . . . ? C6B C1B C2B C3B -1.0(4) . . . . ? S1B C1B C2B C3B -179.4(2) . . . . ? C1B C2B C3B C4B -0.2(4) . . . . ? C2B C3B C4B C5B 1.2(5) . . . . ? C3B C4B C5B C6B -1.0(5) . . . . ? C4B C5B C6B C1B -0.2(4) . . . . ? C4B C5B C6B C7B -179.2(3) . . . . ? C2B C1B C6B C5B 1.1(4) . . . . ? S1B C1B C6B C5B 179.57(19) . . . . ? C2B C1B C6B C7B -179.8(2) . . . . ? S1B C1B C6B C7B -1.4(3) . . . . ? C8B N1B C7B O1B 1.1(3) . . . . ? C8B N1B C7B C6B -178.4(2) . . . . ? C9B O1B C7B N1B 1.2(3) . . . . ? C9B O1B C7B C6B -179.2(2) . . . . ? C5B C6B C7B N1B -178.3(3) . . . . ? C1B C6B C7B N1B 2.7(4) . . . . ? C5B C6B C7B O1B 2.2(3) . . . . ? C1B C6B C7B O1B -176.8(2) . . . . ? C7B N1B C8B C9B -2.8(3) . . . . ? C7B O1B C9B C8B -2.8(3) . . . . ? N1B C8B C9B O1B 3.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 57.48 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.194 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.036 #=== END data_13 _database_code_depnum_ccdc_archive 'CCDC 229427' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 N O S' _chemical_formula_weight 269.35 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 P2(1)2(1)2(1) 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 5.6512(10) _cell_length_b 7.9702(14) _cell_length_c 30.441(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1371.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 44 _cell_measurement_theta_min 6.27 _cell_measurement_theta_max 35.59 _exptl_crystal_description needle _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.85 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type Shelxa _exptl_absorpt_correction_T_min 0.4874 _exptl_absorpt_correction_T_max 0.8356 _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1033 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 22.94 _reflns_number_total 1033 _reflns_number_gt 1000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0573P)^2^+0.2440P] 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 SHELXL _refine_ls_extinction_coef 0.119(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.43(14) _refine_ls_number_reflns 1033 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S S 0.23901(14) 0.36337(7) 0.87497(2) 0.0441(3) Uani 1 1 d . . . O O 0.8129(5) 0.5276(3) 0.78254(7) 0.0674(8) Uani 1 1 d . . . N N 0.6111(5) 0.3192(3) 0.81450(8) 0.0549(8) Uani 1 1 d . . . C1 C 0.3017(5) 0.5725(3) 0.85877(8) 0.0407(7) Uani 1 1 d . . . C2 C 0.1707(7) 0.7080(4) 0.87453(10) 0.0537(9) Uani 1 1 d . . . H2A H 0.0440 0.6874 0.8933 0.044(8) Uiso 1 1 calc R . . C3 C 0.2227(7) 0.8717(3) 0.86321(11) 0.0578(9) Uani 1 1 d . . . H3A H 0.1313 0.9590 0.8743 0.081(12) Uiso 1 1 calc R . . C4 C 0.4091(7) 0.9058(4) 0.83568(10) 0.0594(9) Uani 1 1 d . . . H4A H 0.4461 1.0161 0.8284 0.071(10) Uiso 1 1 calc R . . C5 C 0.5404(7) 0.7755(4) 0.81895(10) 0.0545(9) Uani 1 1 d . . . H5A H 0.6651 0.7992 0.8000 0.068(11) Uiso 1 1 calc R . . C6 C 0.4916(5) 0.6081(3) 0.82957(8) 0.0396(7) Uani 1 1 d . . . C7 C 0.6348(6) 0.4759(3) 0.80943(8) 0.0416(7) Uani 1 1 d . . . C8 C 0.7934(7) 0.2359(4) 0.78794(10) 0.0557(9) Uani 1 1 d . . . H8A H 0.7218 0.1658 0.7655 0.067(10) Uiso 1 1 calc R . . H8B H 0.8948 0.1668 0.8062 0.063(9) Uiso 1 1 calc R . . C9 C 0.9334(7) 0.3785(4) 0.76722(10) 0.0570(9) Uani 1 1 d . . . H9A H 1.0968 0.3771 0.7770 0.060(9) Uiso 1 1 calc R . . H9B H 0.9297 0.3715 0.7354 0.062(9) Uiso 1 1 calc R . . C10 C 0.0045(6) 0.3897(4) 0.91570(9) 0.0483(8) Uani 1 1 d . . . H10A H 0.0521 0.4707 0.9378 0.055(9) Uiso 1 1 calc R . . H10B H -0.1390 0.4298 0.9017 0.063(10) Uiso 1 1 calc R . . C11 C -0.0380(5) 0.2210(3) 0.93655(8) 0.0397(7) Uani 1 1 d . . . C12 C -0.2321(6) 0.1236(4) 0.92534(9) 0.0513(8) Uani 1 1 d . . . H12A H -0.3363 0.1608 0.9038 0.065(10) Uiso 1 1 calc R . . C13 C -0.2722(7) -0.0292(4) 0.94603(11) 0.0622(9) Uani 1 1 d . . . H13A H -0.4022 -0.0942 0.9382 0.102(14) Uiso 1 1 calc R . . C14 C -0.1184(7) -0.0844(4) 0.97827(11) 0.0634(9) Uani 1 1 d . . . H14A H -0.1457 -0.1860 0.9924 0.079(11) Uiso 1 1 calc R . . C15 C 0.0743(7) 0.0110(4) 0.98936(10) 0.0600(9) Uani 1 1 d . . . H15A H 0.1781 -0.0263 1.0109 0.103(14) Uiso 1 1 calc R . . C16 C 0.1150(6) 0.1627(4) 0.96856(9) 0.0495(8) Uani 1 1 d . . . H16A H 0.2468 0.2261 0.9762 0.055(9) 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 S 0.0524(6) 0.0333(4) 0.0468(5) 0.0033(3) 0.0151(4) 0.0026(4) O 0.0703(19) 0.0500(12) 0.0818(15) 0.0047(11) 0.0372(15) 0.0010(13) N 0.0610(19) 0.0400(14) 0.0636(15) -0.0002(11) 0.0244(16) 0.0040(14) C1 0.0467(18) 0.0361(13) 0.0392(13) -0.0019(11) -0.0015(14) 0.0021(14) C2 0.063(2) 0.0431(16) 0.0545(16) -0.0017(13) 0.0150(18) 0.0064(17) C3 0.069(2) 0.0376(15) 0.0671(18) -0.0054(14) 0.009(2) 0.0020(19) C4 0.074(2) 0.0332(15) 0.0709(19) 0.0023(14) 0.004(2) -0.0056(18) C5 0.061(2) 0.0448(16) 0.0578(17) 0.0045(14) 0.0105(18) -0.0055(17) C6 0.0427(17) 0.0367(14) 0.0394(13) -0.0008(11) 0.0022(13) -0.0012(15) C7 0.0451(18) 0.0454(16) 0.0342(13) 0.0030(11) 0.0078(15) -0.0038(15) C8 0.062(2) 0.0520(16) 0.0533(16) -0.0023(14) 0.0147(19) 0.0096(18) C9 0.055(2) 0.066(2) 0.0502(15) -0.0002(14) 0.0146(15) 0.0007(19) C10 0.052(2) 0.0466(17) 0.0462(15) 0.0031(13) 0.0115(15) 0.0063(17) C11 0.0405(18) 0.0428(15) 0.0358(13) -0.0004(11) 0.0089(14) 0.0028(15) C12 0.0410(18) 0.0611(18) 0.0518(16) 0.0034(14) -0.0049(15) 0.004(2) C13 0.049(2) 0.059(2) 0.079(2) 0.0030(16) 0.004(2) -0.012(2) C14 0.068(2) 0.0495(17) 0.072(2) 0.0140(16) 0.003(2) 0.001(2) C15 0.065(2) 0.0554(18) 0.0590(17) 0.0095(15) -0.0113(19) 0.007(2) C16 0.0480(19) 0.0495(16) 0.0511(15) -0.0008(13) -0.0066(15) -0.0027(17) _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 S C1 1.774(3) . ? S C10 1.827(3) . ? O C7 1.361(4) . ? O C9 1.447(4) . ? N C7 1.266(4) . ? N C8 1.469(4) . ? C1 C2 1.395(4) . ? C1 C6 1.422(4) . ? C2 C3 1.381(4) . ? C3 C4 1.373(5) . ? C4 C5 1.374(4) . ? C5 C6 1.400(4) . ? C6 C7 1.463(4) . ? C8 C9 1.522(4) . ? C10 C11 1.506(4) . ? C11 C16 1.383(4) . ? C11 C12 1.387(4) . ? C12 C13 1.390(4) . ? C13 C14 1.383(5) . ? C14 C15 1.370(5) . ? C15 C16 1.384(4) . ? 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 C1 S C10 103.04(13) . . ? C7 O C9 107.1(2) . . ? C7 N C8 107.7(3) . . ? C2 C1 C6 117.4(3) . . ? C2 C1 S 121.7(2) . . ? C6 C1 S 120.8(2) . . ? C3 C2 C1 122.2(3) . . ? C4 C3 C2 120.2(3) . . ? C3 C4 C5 119.4(3) . . ? C4 C5 C6 121.9(3) . . ? C5 C6 C1 118.9(3) . . ? C5 C6 C7 118.7(3) . . ? C1 C6 C7 122.4(2) . . ? N C7 O 116.8(3) . . ? N C7 C6 126.9(3) . . ? O C7 C6 116.3(2) . . ? N C8 C9 104.8(2) . . ? O C9 C8 103.6(2) . . ? C11 C10 S 107.40(19) . . ? C16 C11 C12 118.6(3) . . ? C16 C11 C10 119.8(3) . . ? C12 C11 C10 121.5(3) . . ? C11 C12 C13 120.5(3) . . ? C14 C13 C12 119.9(3) . . ? C15 C14 C13 119.8(3) . . ? C14 C15 C16 120.3(3) . . ? C11 C16 C15 120.8(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 C10 S C1 C2 -4.3(3) . . . . ? C10 S C1 C6 174.6(2) . . . . ? C6 C1 C2 C3 -1.1(5) . . . . ? S C1 C2 C3 177.9(3) . . . . ? C1 C2 C3 C4 -0.2(6) . . . . ? C2 C3 C4 C5 1.1(5) . . . . ? C3 C4 C5 C6 -0.8(5) . . . . ? C4 C5 C6 C1 -0.4(5) . . . . ? C4 C5 C6 C7 178.2(3) . . . . ? C2 C1 C6 C5 1.3(4) . . . . ? S C1 C6 C5 -177.6(2) . . . . ? C2 C1 C6 C7 -177.3(3) . . . . ? S C1 C6 C7 3.8(4) . . . . ? C8 N C7 O -0.4(4) . . . . ? C8 N C7 C6 179.9(3) . . . . ? C9 O C7 N -1.0(4) . . . . ? C9 O C7 C6 178.7(3) . . . . ? C5 C6 C7 N -178.1(4) . . . . ? C1 C6 C7 N 0.5(5) . . . . ? C5 C6 C7 O 2.2(4) . . . . ? C1 C6 C7 O -179.2(2) . . . . ? C7 N C8 C9 1.5(4) . . . . ? C7 O C9 C8 1.9(3) . . . . ? N C8 C9 O -2.0(3) . . . . ? C1 S C10 C11 -171.9(2) . . . . ? S C10 C11 C16 78.7(3) . . . . ? S C10 C11 C12 -103.2(3) . . . . ? C16 C11 C12 C13 0.3(4) . . . . ? C10 C11 C12 C13 -177.9(3) . . . . ? C11 C12 C13 C14 0.4(5) . . . . ? C12 C13 C14 C15 -0.7(5) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? C12 C11 C16 C15 -0.7(4) . . . . ? C10 C11 C16 C15 177.5(3) . . . . ? C14 C15 C16 C11 0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 22.94 _diffrn_measured_fraction_theta_full 0.894 _refine_diff_density_max 0.164 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.030 #=== END data_15 _database_code_depnum_ccdc_archive 'CCDC 229428' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 Br N O Se' _chemical_formula_weight 305.03 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z' 'x-1/2, y, -z-1/2' _cell_length_a 7.3118(6) _cell_length_b 15.2642(12) _cell_length_c 17.2559(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1925.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'thick need' _exptl_crystal_colour 'pale orang' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.8 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.104 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 8.005 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.2223 _exptl_absorpt_correction_T_max 0.6867 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(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 10791 _diffrn_reflns_av_R_equivalents 0.0751 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.36 _reflns_number_total 2379 _reflns_number_gt 1434 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0239P)^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 SHELXL _refine_ls_extinction_coef 0.00329(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2379 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0515 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 Se Se 0.24875(5) 0.407268(16) 0.286189(15) 0.01062(9) Uani 1 1 d . . . Br Br 0.25198(6) 0.441718(19) 0.439643(15) 0.01856(9) Uani 1 1 d . . . O O 0.3462(3) 0.28103(13) 0.08627(11) 0.0142(5) Uani 1 1 d . . . N N 0.2618(4) 0.37863(14) 0.17473(13) 0.0114(5) Uani 1 1 d . . . C1 C 0.3254(4) 0.28791(18) 0.29589(17) 0.0099(6) Uani 1 1 d . . . C2 C 0.3500(4) 0.24155(19) 0.36510(18) 0.0138(7) Uani 1 1 d . . . H2A H 0.3275 0.2688 0.4137 0.017 Uiso 1 1 calc R . . C3 C 0.4074(5) 0.1555(2) 0.36159(18) 0.0173(7) Uani 1 1 d . . . H3A H 0.4234 0.1236 0.4084 0.021 Uiso 1 1 calc R . . C4 C 0.4427(4) 0.11401(19) 0.29093(19) 0.0157(7) Uani 1 1 d . . . H4A H 0.4865 0.0554 0.2903 0.019 Uiso 1 1 calc R . . C5 C 0.4140(4) 0.1580(2) 0.22210(18) 0.0142(7) Uani 1 1 d . . . H5A H 0.4335 0.1297 0.1738 0.017 Uiso 1 1 calc R . . C6 C 0.3554(4) 0.24540(19) 0.22521(16) 0.0107(6) Uani 1 1 d . . . C7 C 0.3207(4) 0.3012(2) 0.16024(17) 0.0105(6) Uani 1 1 d . . . C8 C 0.2871(4) 0.35914(18) 0.04134(17) 0.0162(8) Uani 1 1 d . . . H8A H 0.1741 0.3465 0.0118 0.019 Uiso 1 1 calc R . . H8B H 0.3839 0.3777 0.0047 0.019 Uiso 1 1 calc R . . C9 C 0.2521(5) 0.43110(17) 0.10349(15) 0.0141(6) Uani 1 1 d . . . H9A H 0.3478 0.4770 0.1023 0.017 Uiso 1 1 calc R . . H9B H 0.1305 0.4586 0.0970 0.017 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 Se 0.01358(16) 0.00864(13) 0.00964(14) -0.00095(10) -0.0004(2) 0.00049(17) Br 0.02440(19) 0.02119(16) 0.01008(14) -0.00581(11) 0.0000(2) 0.00155(19) O 0.0233(14) 0.0097(11) 0.0096(11) 0.0001(9) 0.0000(10) 0.0014(10) N 0.0175(14) 0.0100(10) 0.0068(10) 0.0001(8) -0.0018(14) 0.0004(14) C1 0.0093(16) 0.0103(14) 0.0102(15) 0.0006(12) -0.0016(12) -0.0018(12) C2 0.0174(19) 0.0120(15) 0.0120(15) -0.0004(12) -0.0022(14) -0.0017(14) C3 0.024(2) 0.0136(15) 0.0146(16) 0.0071(14) -0.0054(14) -0.0022(14) C4 0.0164(18) 0.0066(15) 0.0240(18) 0.0008(13) 0.0002(15) -0.0002(13) C5 0.0155(19) 0.0122(15) 0.0149(17) -0.0024(13) 0.0004(14) 0.0001(13) C6 0.0098(17) 0.0095(14) 0.0128(16) -0.0009(12) -0.0008(13) -0.0006(13) C7 0.0100(16) 0.0127(15) 0.0088(14) -0.0012(12) -0.0018(12) -0.0022(12) C8 0.028(3) 0.0110(14) 0.0098(14) 0.0010(11) -0.0047(13) 0.0042(13) C9 0.0247(17) 0.0115(13) 0.0062(12) 0.0024(10) -0.0017(19) 0.0046(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 Se C1 1.913(3) . ? Se N 1.975(2) . ? Se Br 2.6998(4) . ? O C7 1.326(3) . ? O C8 1.486(3) . ? N C7 1.283(4) . ? N C9 1.469(3) . ? C1 C6 1.399(4) . ? C1 C2 1.400(4) . ? C2 C3 1.380(4) . ? C3 C4 1.398(4) . ? C4 C5 1.380(4) . ? C5 C6 1.402(4) . ? C6 C7 1.431(4) . ? C8 C9 1.556(4) . ? 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 C1 Se N 81.97(11) . . ? C1 Se Br 95.57(9) . . ? N Se Br 176.37(8) . . ? C7 O C8 106.0(2) . . ? C7 N C9 110.8(2) . . ? C7 N Se 114.22(19) . . ? C9 N Se 133.80(17) . . ? C6 C1 C2 119.3(3) . . ? C6 C1 Se 114.3(2) . . ? C2 C1 Se 126.4(2) . . ? C3 C2 C1 118.9(3) . . ? C2 C3 C4 121.7(3) . . ? C5 C4 C3 120.1(3) . . ? C4 C5 C6 118.4(3) . . ? C1 C6 C5 121.5(3) . . ? C1 C6 C7 112.3(3) . . ? C5 C6 C7 126.2(3) . . ? N C7 O 116.7(3) . . ? N C7 C6 117.1(3) . . ? O C7 C6 126.2(3) . . ? O C8 C9 104.7(2) . . ? N C9 C8 100.6(2) . . ? 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 C1 Se N C7 -3.5(2) . . . . ? Br Se N C7 44.1(12) . . . . ? C1 Se N C9 -169.7(3) . . . . ? Br Se N C9 -122.2(10) . . . . ? N Se C1 C6 1.9(2) . . . . ? Br Se C1 C6 -175.4(2) . . . . ? N Se C1 C2 -177.1(3) . . . . ? Br Se C1 C2 5.6(3) . . . . ? C6 C1 C2 C3 1.5(5) . . . . ? Se C1 C2 C3 -179.5(2) . . . . ? C1 C2 C3 C4 0.5(5) . . . . ? C2 C3 C4 C5 -2.4(5) . . . . ? C3 C4 C5 C6 2.2(5) . . . . ? C2 C1 C6 C5 -1.6(5) . . . . ? Se C1 C6 C5 179.3(2) . . . . ? C2 C1 C6 C7 178.8(3) . . . . ? Se C1 C6 C7 -0.3(4) . . . . ? C4 C5 C6 C1 -0.2(5) . . . . ? C4 C5 C6 C7 179.3(3) . . . . ? C9 N C7 O -5.3(4) . . . . ? Se N C7 O -174.7(2) . . . . ? C9 N C7 C6 173.7(3) . . . . ? Se N C7 C6 4.3(4) . . . . ? C8 O C7 N -2.3(4) . . . . ? C8 O C7 C6 178.8(3) . . . . ? C1 C6 C7 N -2.7(4) . . . . ? C5 C6 C7 N 177.7(3) . . . . ? C1 C6 C7 O 176.3(3) . . . . ? C5 C6 C7 O -3.3(5) . . . . ? C7 O C8 C9 8.2(3) . . . . ? C7 N C9 C8 9.8(4) . . . . ? Se N C9 C8 176.4(2) . . . . ? O C8 C9 N -10.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.712 _refine_diff_density_min -0.863 _refine_diff_density_rms 0.171 # === END data_16 _database_code_depnum_ccdc_archive 'CCDC 229429' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 I2 N2 O2 Se2' _chemical_formula_weight 704.05 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 15.416(3) _cell_length_b 17.917(3) _cell_length_c 7.8119(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.816(4) _cell_angle_gamma 90.00 _cell_volume 2103.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow-ora _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.88 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 6.464 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.726571 _exptl_absorpt_correction_T_max 0.928082 _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 '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 18422 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_sigmaI/netI 0.1368 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 29.10 _reflns_number_total 5193 _reflns_number_gt 2110 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0072P)^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 SHELXL _refine_ls_extinction_coef 0.00035(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5193 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1363 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0456 _refine_ls_wR_factor_gt 0.0370 _refine_ls_goodness_of_fit_ref 0.783 _refine_ls_restrained_S_all 0.783 _refine_ls_shift/su_max 0.002 _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 I1 I 0.17413(3) 0.937594(19) 0.36289(5) 0.06501(14) Uani 1 1 d . . . I2 I -0.33945(3) 0.553132(19) 0.64882(5) 0.07049(15) Uani 1 1 d . . . Se1 Se 0.13836(3) 0.77911(3) 0.36555(6) 0.04232(15) Uani 1 1 d . . . Se2 Se -0.36135(3) 0.71103(3) 0.62200(6) 0.04494(16) Uani 1 1 d . . . O1 O 0.0115(2) 0.5839(2) 0.3980(4) 0.0670(11) Uani 1 1 d . . . O2 O -0.4739(2) 0.91551(18) 0.5059(4) 0.0538(9) Uani 1 1 d . . . N1 N 0.1115(3) 0.6690(2) 0.3691(5) 0.0441(11) Uani 1 1 d . . . N2 N -0.3780(3) 0.8242(2) 0.6056(5) 0.0436(11) Uani 1 1 d . . . C11 C 0.0195(3) 0.7867(3) 0.4028(5) 0.0393(13) Uani 1 1 d . . . C12 C -0.0271(4) 0.8508(3) 0.4172(6) 0.0500(15) Uani 1 1 d . . . H12A H -0.0005 0.8971 0.4116 0.060 Uiso 1 1 calc R . . C13 C -0.1128(4) 0.8467(3) 0.4398(6) 0.0681(18) Uani 1 1 d . . . H13A H -0.1444 0.8904 0.4472 0.082 Uiso 1 1 calc R . . C14 C -0.1521(4) 0.7786(4) 0.4516(6) 0.0646(17) Uani 1 1 d . . . H14A H -0.2100 0.7769 0.4684 0.077 Uiso 1 1 calc R . . C15 C -0.1081(4) 0.7135(3) 0.4392(6) 0.0592(16) Uani 1 1 d . . . H15A H -0.1352 0.6678 0.4483 0.071 Uiso 1 1 calc R . . C16 C -0.0221(4) 0.7167(3) 0.4127(5) 0.0407(13) Uani 1 1 d . . . C17 C 0.0332(4) 0.6555(3) 0.3950(6) 0.0475(15) Uani 1 1 d . . . C18 C 0.1621(3) 0.5994(3) 0.3610(6) 0.0565(16) Uani 1 1 d . . . H18A H 0.2107 0.5936 0.4628 0.068 Uiso 1 1 calc R . . H18B H 0.1845 0.5964 0.2547 0.068 Uiso 1 1 calc R . . C19 C 0.0863(4) 0.5427(3) 0.3609(7) 0.0748(19) Uani 1 1 d . . . H19C H 0.0694 0.5183 0.2475 0.090 Uiso 1 1 calc R . . H19A H 0.1058 0.5048 0.4499 0.090 Uiso 1 1 calc R . . C21 C -0.4790(3) 0.7130(3) 0.4739(6) 0.0402(12) Uani 1 1 d . . . C22 C -0.5300(4) 0.6519(3) 0.4059(6) 0.0480(15) Uani 1 1 d . . . H22A H -0.5087 0.6037 0.4313 0.058 Uiso 1 1 calc R . . C23 C -0.6124(4) 0.6639(3) 0.3003(7) 0.0606(17) Uani 1 1 d . . . H23A H -0.6462 0.6227 0.2536 0.073 Uiso 1 1 calc R . . C24 C -0.6478(4) 0.7346(4) 0.2600(7) 0.0604(16) Uani 1 1 d . . . H24A H -0.7036 0.7405 0.1861 0.072 Uiso 1 1 calc R . . C25 C -0.5990(4) 0.7956(3) 0.3308(6) 0.0481(14) Uani 1 1 d . . . H25A H -0.6222 0.8435 0.3087 0.058 Uiso 1 1 calc R . . C26 C -0.5143(3) 0.7849(3) 0.4364(6) 0.0386(12) Uani 1 1 d . . . C27 C -0.4560(4) 0.8434(3) 0.5163(6) 0.0433(14) Uani 1 1 d . . . C28 C -0.3262(3) 0.8912(2) 0.6701(6) 0.0513(15) Uani 1 1 d . . . H28A H -0.2756 0.8968 0.6163 0.062 Uiso 1 1 calc R . . H28B H -0.3055 0.8901 0.7967 0.062 Uiso 1 1 calc R . . C29 C -0.3940(4) 0.9529(3) 0.6129(6) 0.0578(15) Uani 1 1 d . . . H29A H -0.4082 0.9772 0.7142 0.069 Uiso 1 1 calc R . . H29B H -0.3713 0.9900 0.5438 0.069 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 I1 0.0708(3) 0.0509(3) 0.0738(3) -0.0004(2) 0.0172(2) -0.0172(2) I2 0.0852(4) 0.0439(2) 0.0772(3) 0.0099(2) 0.0070(2) 0.0093(2) Se1 0.0330(4) 0.0517(3) 0.0423(3) 0.0006(3) 0.0084(3) -0.0001(3) Se2 0.0350(4) 0.0505(4) 0.0487(4) 0.0008(3) 0.0079(3) -0.0007(3) O1 0.070(3) 0.049(3) 0.082(3) -0.002(2) 0.018(2) -0.009(2) O2 0.042(3) 0.038(2) 0.080(3) 0.0039(19) 0.010(2) 0.0068(19) N1 0.048(4) 0.033(3) 0.051(3) 0.001(2) 0.011(3) 0.004(2) N2 0.044(3) 0.033(3) 0.053(3) -0.006(2) 0.010(3) -0.001(2) C11 0.034(3) 0.054(4) 0.028(3) 0.001(3) 0.003(2) -0.004(3) C12 0.036(4) 0.054(4) 0.060(4) -0.006(3) 0.012(3) 0.009(3) C13 0.056(5) 0.083(5) 0.066(4) 0.006(3) 0.014(4) 0.028(4) C14 0.037(4) 0.100(5) 0.059(4) 0.006(4) 0.014(3) 0.004(4) C15 0.045(5) 0.071(5) 0.058(4) 0.009(3) 0.004(3) -0.014(4) C16 0.034(4) 0.056(4) 0.028(3) 0.002(3) 0.000(3) 0.000(3) C17 0.059(5) 0.050(4) 0.032(3) 0.003(3) 0.006(3) -0.011(4) C18 0.068(5) 0.040(3) 0.064(4) -0.001(3) 0.021(3) 0.013(3) C19 0.097(6) 0.037(4) 0.088(5) -0.008(3) 0.015(4) -0.005(4) C21 0.021(3) 0.060(4) 0.040(3) 0.002(3) 0.008(2) -0.004(3) C22 0.038(4) 0.053(4) 0.050(4) -0.002(3) 0.005(3) -0.010(3) C23 0.044(5) 0.068(4) 0.073(5) -0.014(3) 0.020(4) -0.019(3) C24 0.032(4) 0.094(5) 0.054(4) 0.001(4) 0.008(3) 0.001(4) C25 0.038(4) 0.054(4) 0.053(4) -0.002(3) 0.013(3) 0.012(3) C26 0.031(4) 0.042(3) 0.046(3) 0.003(3) 0.014(3) 0.000(3) C27 0.046(4) 0.043(4) 0.045(4) 0.003(3) 0.019(3) 0.004(3) C28 0.048(4) 0.039(3) 0.066(4) -0.003(3) 0.012(3) -0.002(3) C29 0.057(4) 0.038(3) 0.076(4) -0.009(3) 0.010(4) -0.005(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 I1 Se1 2.8935(8) . ? I2 Se2 2.8513(8) . ? Se1 C11 1.923(5) . ? Se1 N1 2.018(4) . ? Se2 C21 1.923(5) . ? Se2 N2 2.044(4) . ? O1 C17 1.327(5) . ? O1 C19 1.452(6) . ? O2 C27 1.320(5) . ? O2 C29 1.485(5) . ? N1 C17 1.289(6) . ? N1 C18 1.479(5) . ? N2 C27 1.295(6) . ? N2 C28 1.468(5) . ? C11 C12 1.372(5) . ? C11 C16 1.418(6) . ? C12 C13 1.373(6) . ? C12 H12A 0.9300 . ? C13 C14 1.375(6) . ? C13 H13A 0.9300 . ? C14 C15 1.363(6) . ? C14 H14A 0.9300 . ? C15 C16 1.387(6) . ? C15 H15A 0.9300 . ? C16 C17 1.416(6) . ? C18 C19 1.548(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19C 0.9700 . ? C19 H19A 0.9700 . ? C21 C22 1.383(6) . ? C21 C26 1.404(6) . ? C22 C23 1.369(6) . ? C22 H22A 0.9300 . ? C23 C24 1.388(6) . ? C23 H23A 0.9300 . ? C24 C25 1.372(6) . ? C24 H24A 0.9300 . ? C25 C26 1.395(6) . ? C25 H25A 0.9300 . ? C26 C27 1.431(6) . ? C28 C29 1.518(6) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? 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 C11 Se1 N1 82.03(19) . . ? C11 Se1 I1 96.97(16) . . ? N1 Se1 I1 178.97(13) . . ? C21 Se2 N2 81.7(2) . . ? C21 Se2 I2 98.21(16) . . ? N2 Se2 I2 179.18(11) . . ? C17 O1 C19 105.8(4) . . ? C27 O2 C29 105.7(4) . . ? C17 N1 C18 111.7(4) . . ? C17 N1 Se1 112.8(3) . . ? C18 N1 Se1 135.3(4) . . ? C27 N2 C28 109.7(4) . . ? C27 N2 Se2 112.7(4) . . ? C28 N2 Se2 137.6(4) . . ? C12 C11 C16 119.0(5) . . ? C12 C11 Se1 127.2(4) . . ? C16 C11 Se1 113.8(4) . . ? C11 C12 C13 120.1(5) . . ? C11 C12 H12A 119.9 . . ? C13 C12 H12A 119.9 . . ? C12 C13 C14 120.5(5) . . ? C12 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C15 C14 C13 121.3(5) . . ? C15 C14 H14A 119.3 . . ? C13 C14 H14A 119.3 . . ? C14 C15 C16 118.9(5) . . ? C14 C15 H15A 120.6 . . ? C16 C15 H15A 120.6 . . ? C15 C16 C17 126.8(5) . . ? C15 C16 C11 120.2(5) . . ? C17 C16 C11 113.0(5) . . ? N1 C17 O1 115.7(5) . . ? N1 C17 C16 118.4(5) . . ? O1 C17 C16 126.0(6) . . ? N1 C18 C19 98.5(4) . . ? N1 C18 H18A 112.1 . . ? C19 C18 H18A 112.1 . . ? N1 C18 H18B 112.1 . . ? C19 C18 H18B 112.1 . . ? H18A C18 H18B 109.7 . . ? O1 C19 C18 107.4(4) . . ? O1 C19 H19C 110.2 . . ? C18 C19 H19C 110.2 . . ? O1 C19 H19A 110.2 . . ? C18 C19 H19A 110.2 . . ? H19C C19 H19A 108.5 . . ? C22 C21 C26 119.0(5) . . ? C22 C21 Se2 126.6(4) . . ? C26 C21 Se2 114.3(4) . . ? C23 C22 C21 118.7(5) . . ? C23 C22 H22A 120.6 . . ? C21 C22 H22A 120.6 . . ? C22 C23 C24 123.0(5) . . ? C22 C23 H23A 118.5 . . ? C24 C23 H23A 118.5 . . ? C25 C24 C23 118.9(6) . . ? C25 C24 H24A 120.5 . . ? C23 C24 H24A 120.5 . . ? C24 C25 C26 119.1(5) . . ? C24 C25 H25A 120.5 . . ? C26 C25 H25A 120.5 . . ? C25 C26 C21 121.2(5) . . ? C25 C26 C27 124.9(5) . . ? C21 C26 C27 113.9(5) . . ? N2 C27 O2 116.7(5) . . ? N2 C27 C26 117.3(5) . . ? O2 C27 C26 126.0(6) . . ? N2 C28 C29 102.0(4) . . ? N2 C28 H28A 111.4 . . ? C29 C28 H28A 111.4 . . ? N2 C28 H28B 111.4 . . ? C29 C28 H28B 111.4 . . ? H28A C28 H28B 109.2 . . ? O2 C29 C28 105.6(4) . . ? O2 C29 H29A 110.6 . . ? C28 C29 H29A 110.6 . . ? O2 C29 H29B 110.6 . . ? C28 C29 H29B 110.6 . . ? H29A C29 H29B 108.8 . . ? 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 C11 Se1 N1 C17 -0.8(3) . . . . ? I1 Se1 N1 C17 12(7) . . . . ? C11 Se1 N1 C18 -175.7(4) . . . . ? I1 Se1 N1 C18 -163(6) . . . . ? C21 Se2 N2 C27 2.8(3) . . . . ? I2 Se2 N2 C27 -80(10) . . . . ? C21 Se2 N2 C28 -178.6(5) . . . . ? I2 Se2 N2 C28 99(10) . . . . ? N1 Se1 C11 C12 -178.9(4) . . . . ? I1 Se1 C11 C12 1.3(4) . . . . ? N1 Se1 C11 C16 0.0(3) . . . . ? I1 Se1 C11 C16 -179.8(3) . . . . ? C16 C11 C12 C13 -0.3(7) . . . . ? Se1 C11 C12 C13 178.5(4) . . . . ? C11 C12 C13 C14 1.2(8) . . . . ? C12 C13 C14 C15 -0.8(8) . . . . ? C13 C14 C15 C16 -0.5(8) . . . . ? C14 C15 C16 C17 -179.4(5) . . . . ? C14 C15 C16 C11 1.4(7) . . . . ? C12 C11 C16 C15 -1.0(6) . . . . ? Se1 C11 C16 C15 -180.0(3) . . . . ? C12 C11 C16 C17 179.7(4) . . . . ? Se1 C11 C16 C17 0.7(5) . . . . ? C18 N1 C17 O1 -4.1(6) . . . . ? Se1 N1 C17 O1 179.7(3) . . . . ? C18 N1 C17 C16 177.6(4) . . . . ? Se1 N1 C17 C16 1.4(6) . . . . ? C19 O1 C17 N1 -2.6(6) . . . . ? C19 O1 C17 C16 175.5(5) . . . . ? C15 C16 C17 N1 179.3(5) . . . . ? C11 C16 C17 N1 -1.4(6) . . . . ? C15 C16 C17 O1 1.2(8) . . . . ? C11 C16 C17 O1 -179.5(4) . . . . ? C17 N1 C18 C19 8.2(5) . . . . ? Se1 N1 C18 C19 -176.8(3) . . . . ? C17 O1 C19 C18 7.8(5) . . . . ? N1 C18 C19 O1 -9.3(5) . . . . ? N2 Se2 C21 C22 179.5(4) . . . . ? I2 Se2 C21 C22 -1.4(4) . . . . ? N2 Se2 C21 C26 -1.3(3) . . . . ? I2 Se2 C21 C26 177.9(3) . . . . ? C26 C21 C22 C23 1.7(7) . . . . ? Se2 C21 C22 C23 -179.1(4) . . . . ? C21 C22 C23 C24 -0.8(8) . . . . ? C22 C23 C24 C25 -1.1(8) . . . . ? C23 C24 C25 C26 2.1(7) . . . . ? C24 C25 C26 C21 -1.2(7) . . . . ? C24 C25 C26 C27 179.0(4) . . . . ? C22 C21 C26 C25 -0.7(6) . . . . ? Se2 C21 C26 C25 -180.0(3) . . . . ? C22 C21 C26 C27 179.1(4) . . . . ? Se2 C21 C26 C27 -0.2(5) . . . . ? C28 N2 C27 O2 -2.0(6) . . . . ? Se2 N2 C27 O2 177.0(3) . . . . ? C28 N2 C27 C26 177.3(4) . . . . ? Se2 N2 C27 C26 -3.7(5) . . . . ? C29 O2 C27 N2 -2.0(6) . . . . ? C29 O2 C27 C26 178.7(4) . . . . ? C25 C26 C27 N2 -177.5(4) . . . . ? C21 C26 C27 N2 2.7(6) . . . . ? C25 C26 C27 O2 1.7(8) . . . . ? C21 C26 C27 O2 -178.1(4) . . . . ? C27 N2 C28 C29 5.0(5) . . . . ? Se2 N2 C28 C29 -173.7(3) . . . . ? C27 O2 C29 C28 5.0(5) . . . . ? N2 C28 C29 O2 -5.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.516 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.100