# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Andreas Decken' ;Department of Chemistry University of New Brunswick Fredericton, NB E3B 5A3 Canada ; 'Glen Briand' ;Department of Chemistry Mount Allison University 63C York Street Sackville, NB E4L 1G8 Canada ; N.S.Hamilton '' _publ_contact_author_address ;Department of Chemistry University of New Brunswick Fredericton, NB E3B 5A3 Canada ; _publ_contact_author_email adecken@unb.ca _publ_contact_author_fax '(506) 453-4981' _publ_contact_author_phone '(506) 453-4875' _publ_contact_author_name 'Andreas Decken' data_gb080693 _database_code_depnum_ccdc_archive 'CCDC 747574' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; Hydrogen atoms were included in calculated positions and refined using a riding model. Disordered solvent (hexane) could not be modelleled properly. The crystal was twinned and the structure refined using all data. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 In2 O2' _chemical_formula_sum 'C20 H30 In2 O2' _chemical_formula_weight 532.08 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' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_int_tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 27.368(6) _cell_length_b 27.368(6) _cell_length_c 8.447(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5479(2) _cell_formula_units_Z 9 _cell_measurement_temperature 198(1) _cell_measurement_reflns_used 8200 _cell_measurement_theta_min 2.563 _cell_measurement_theta_max 28.3025 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.375 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2376 _exptl_absorpt_coefficient_mu 1.901 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5358 _exptl_absorpt_correction_T_max 0.8706 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 198(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2758 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2758 _reflns_number_gt 2354 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0864P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2758 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1549 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.204 _refine_ls_restrained_S_all 1.204 _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 In1 In 0.426388(10) 0.970989(10) 0.00054(3) 0.03674(11) Uani 1 1 d . . . O1 O 0.49311(8) 0.95111(9) 0.0454(3) 0.0328(5) Uani 1 1 d . . . C1 C 0.3900(2) 0.9415(2) -0.2279(6) 0.0775(15) Uani 1 1 d . . . H1A H 0.3503 0.9121 -0.2160 0.116 Uiso 1 1 calc R . . H1B H 0.4105 0.9258 -0.2831 0.116 Uiso 1 1 calc R . . H1C H 0.3923 0.9729 -0.2894 0.116 Uiso 1 1 calc R . . C2 C 0.38986(19) 0.97811(18) 0.2173(6) 0.0644(12) Uani 1 1 d . . . H2A H 0.3722 1.0012 0.1998 0.097 Uiso 1 1 calc R . . H2B H 0.4194 0.9959 0.2980 0.097 Uiso 1 1 calc R . . H2C H 0.3612 0.9405 0.2532 0.097 Uiso 1 1 calc R . . C3 C 0.48916(13) 0.90215(13) 0.1000(4) 0.0326(7) Uani 1 1 d . . . C4 C 0.48736(15) 0.89204(17) 0.2625(4) 0.0459(9) Uani 1 1 d . . . C5 C 0.48301(18) 0.8415(2) 0.3112(6) 0.0670(13) Uani 1 1 d . . . H5 H 0.4819 0.8337 0.4212 0.080 Uiso 1 1 calc R . . C6 C 0.48031(18) 0.8025(2) 0.2040(8) 0.0774(17) Uani 1 1 d . . . H6 H 0.4771 0.7682 0.2401 0.093 Uiso 1 1 calc R . . C7 C 0.48228(17) 0.81301(17) 0.0473(7) 0.0698(15) Uani 1 1 d . . . H7 H 0.4807 0.7858 -0.0256 0.084 Uiso 1 1 calc R . . C8 C 0.48656(14) 0.86260(15) -0.0099(5) 0.0460(9) Uani 1 1 d . . . C9 C 0.4873(2) 0.9320(2) 0.3801(5) 0.0717(14) Uani 1 1 d . . . H9A H 0.5018 0.9692 0.3309 0.108 Uiso 1 1 calc R . . H9B H 0.5115 0.9351 0.4697 0.108 Uiso 1 1 calc R . . H9C H 0.4488 0.9183 0.4177 0.108 Uiso 1 1 calc R . . C10 C 0.4863(2) 0.87292(19) -0.1845(5) 0.0716(14) Uani 1 1 d . . . H10A H 0.4842 0.8410 -0.2432 0.107 Uiso 1 1 calc R . . H10B H 0.5211 0.9076 -0.2134 0.107 Uiso 1 1 calc R . . H10C H 0.4536 0.8769 -0.2108 0.107 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 In1 0.03056(16) 0.03236(16) 0.04648(18) 0.00241(10) -0.00164(10) 0.01511(11) O1 0.0341(12) 0.0276(11) 0.0381(13) 0.0026(9) 0.0018(9) 0.0166(10) C1 0.059(3) 0.076(3) 0.064(3) 0.004(2) -0.031(2) 0.008(2) C2 0.058(3) 0.055(3) 0.084(3) 0.004(2) 0.031(2) 0.030(2) C3 0.0258(15) 0.0264(16) 0.0452(19) 0.0046(14) 0.0010(14) 0.0128(13) C4 0.0321(18) 0.049(2) 0.050(2) 0.0142(18) -0.0034(16) 0.0156(16) C5 0.042(2) 0.076(3) 0.082(3) 0.043(3) 0.003(2) 0.029(2) C6 0.048(3) 0.054(3) 0.140(5) 0.045(3) 0.014(3) 0.033(2) C7 0.043(2) 0.037(2) 0.139(5) 0.006(3) 0.022(3) 0.0265(19) C8 0.0290(17) 0.0326(19) 0.073(3) -0.0026(17) 0.0105(17) 0.0131(15) C9 0.074(3) 0.080(3) 0.035(2) 0.006(2) -0.003(2) 0.019(3) C10 0.080(3) 0.055(3) 0.064(3) -0.019(2) 0.023(2) 0.022(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 In1 C1 2.137(4) . ? In1 C2 2.141(4) . ? In1 O1 2.184(2) . ? In1 O1 2.203(2) 10_675 ? O1 C3 1.369(4) . ? O1 In1 2.203(2) 10_675 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.396(5) . ? C3 C8 1.401(5) . ? C4 C5 1.391(6) . ? C4 C9 1.479(6) . ? C5 C6 1.372(7) . ? C5 H5 0.9500 . ? C6 C7 1.350(8) . ? C6 H6 0.9500 . ? C7 C8 1.389(6) . ? C7 H7 0.9500 . ? C8 C10 1.502(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 C1 In1 C2 131.0(2) . . ? C1 In1 O1 110.66(17) . . ? C2 In1 O1 111.16(15) . . ? C1 In1 O1 104.99(15) . 10_675 ? C2 In1 O1 110.44(14) . 10_675 ? O1 In1 O1 73.47(9) . 10_675 ? C3 O1 In1 129.46(18) . . ? C3 O1 In1 123.92(18) . 10_675 ? In1 O1 In1 106.53(9) . 10_675 ? In1 C1 H1A 109.5 . . ? In1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? In1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? In1 C2 H2A 109.5 . . ? In1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? In1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O1 C3 C4 120.2(3) . . ? O1 C3 C8 118.8(3) . . ? C4 C3 C8 121.0(3) . . ? C5 C4 C3 117.7(4) . . ? C5 C4 C9 120.4(4) . . ? C3 C4 C9 121.8(3) . . ? C6 C5 C4 121.5(4) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C7 C6 C5 120.1(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 121.5(5) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C7 C8 C3 118.1(4) . . ? C7 C8 C10 121.2(4) . . ? C3 C8 C10 120.6(3) . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.550 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.161 data_gb080701 _database_code_depnum_ccdc_archive 'CCDC 747575' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; Hydrogen atoms were included in calculated positions and refined using a riding model. The molecule was disordered over two sites with equal occupancy factors. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H35 In O' _chemical_formula_sum 'C20 H35 In O' _chemical_formula_weight 406.30 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' In In -0.7276 1.3100 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_space_group_name_Hall '-P 2yb' _symmetry_int_tables_number 11 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 9.4341(17) _cell_length_b 9.9553(18) _cell_length_c 11.237(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.514(2) _cell_angle_gamma 90.00 _cell_volume 1034.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 198(1) _cell_measurement_reflns_used 6417 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 28.33 _exptl_crystal_description Irregular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 1.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.525024 _exptl_absorpt_correction_T_max 0.631296 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 198(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7196 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2453 _reflns_number_gt 2417 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0564P)^2^+9.3053P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2453 _refine_ls_number_parameters 202 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.2006 _refine_ls_wR_factor_gt 0.2004 _refine_ls_goodness_of_fit_ref 1.281 _refine_ls_restrained_S_all 1.278 _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 In1 In 0.56689(8) 0.7500 0.42303(6) 0.0408(3) Uani 1 2 d S . . O1 O 0.4265(10) 0.5939(12) 0.3728(8) 0.041(2) Uani 0.50 1 d P . . C1 C 0.528(2) 0.907(2) 0.3007(16) 0.063(5) Uani 0.50 1 d P . . H1A H 0.4595 0.8779 0.2277 0.095 Uiso 0.50 1 calc PR . . H1B H 0.6188 0.9348 0.2785 0.095 Uiso 0.50 1 calc PR . . H1C H 0.4865 0.9829 0.3377 0.095 Uiso 0.50 1 calc PR . . C2 C 0.7130(19) 0.8138(19) 0.5803(13) 0.053(4) Uani 0.50 1 d P . . H2A H 0.6743 0.7906 0.6524 0.080 Uiso 0.50 1 calc PR . . H2B H 0.7260 0.9113 0.5772 0.080 Uiso 0.50 1 calc PR . . H2C H 0.8063 0.7690 0.5844 0.080 Uiso 0.50 1 calc PR . . C3 C 0.3287(14) 0.6061(15) 0.2684(11) 0.035(3) Uani 0.50 1 d P . . C4 C 0.3634(14) 0.5636(15) 0.1566(11) 0.035(3) Uani 0.50 1 d P . . C5 C 0.2630(14) 0.5880(16) 0.0475(11) 0.037(3) Uani 0.50 1 d P . . H5 H 0.2885 0.5643 -0.0274 0.045 Uiso 0.50 1 calc PR . . C6 C 0.1290(14) 0.6453(14) 0.0456(12) 0.034(3) Uani 0.50 1 d P . . C7 C 0.0932(13) 0.6771(14) 0.1576(11) 0.034(3) Uani 0.50 1 d P . . H7 H 0.0002 0.7133 0.1584 0.040 Uiso 0.50 1 calc PR . . C8 C 0.1900(14) 0.6574(14) 0.2687(12) 0.034(3) Uani 0.50 1 d P . . C9 C 0.5050(15) 0.4892(17) 0.1530(12) 0.040(3) Uani 0.50 1 d P . . C10 C 0.6432(16) 0.5752(19) 0.2035(16) 0.051(4) Uani 0.50 1 d P . . H10A H 0.6155 0.6696 0.2089 0.076 Uiso 0.50 1 calc PR . . H10B H 0.7116 0.5672 0.1487 0.076 Uiso 0.50 1 calc PR . . H10C H 0.6887 0.5426 0.2844 0.076 Uiso 0.50 1 calc PR . . C11 C 0.509(2) 0.351(2) 0.2249(17) 0.060(5) Uani 0.50 1 d P . . H11A H 0.5085 0.3694 0.3106 0.090 Uiso 0.50 1 calc PR . . H11B H 0.5967 0.3014 0.2186 0.090 Uiso 0.50 1 calc PR . . H11C H 0.4236 0.2974 0.1899 0.090 Uiso 0.50 1 calc PR . . C12 C 0.515(2) 0.446(2) 0.0228(14) 0.061(5) Uani 0.50 1 d P . . H12A H 0.4308 0.3906 -0.0115 0.092 Uiso 0.50 1 calc PR . . H12B H 0.6037 0.3950 0.0249 0.092 Uiso 0.50 1 calc PR . . H12C H 0.5155 0.5266 -0.0277 0.092 Uiso 0.50 1 calc PR . . C13 C 0.0194(16) 0.6707(16) -0.0755(12) 0.033(3) Uani 0.50 1 d P . . C14 C 0.012(3) 0.552(3) -0.156(2) 0.098(10) Uani 0.50 1 d PU . . H14A H -0.0145 0.4727 -0.1134 0.147 Uiso 0.50 1 calc PR . . H14B H 0.1064 0.5375 -0.1773 0.147 Uiso 0.50 1 calc PR . . H14C H -0.0611 0.5673 -0.2298 0.147 Uiso 0.50 1 calc PR . . C15 C 0.077(3) 0.790(4) -0.136(3) 0.15(2) Uani 0.50 1 d PU . . H15A H 0.1287 0.7581 -0.1983 0.224 Uiso 0.50 1 calc PR . . H15B H 0.1434 0.8425 -0.0752 0.224 Uiso 0.50 1 calc PR . . H15C H -0.0039 0.8475 -0.1746 0.224 Uiso 0.50 1 calc PR . . C16 C -0.127(2) 0.698(7) -0.0584(19) 0.16(3) Uani 0.50 1 d PU . . H16A H -0.1486 0.7932 -0.0729 0.236 Uiso 0.50 1 calc PR . . H16B H -0.1340 0.6745 0.0249 0.236 Uiso 0.50 1 calc PR . . H16C H -0.1954 0.6435 -0.1157 0.236 Uiso 0.50 1 calc PR . . C17 C 0.1393(15) 0.6851(15) 0.3892(12) 0.037(3) Uani 0.50 1 d P . . C18 C 0.138(2) 0.556(2) 0.4582(16) 0.060(5) Uani 0.50 1 d P . . H18A H 0.0702 0.4928 0.4096 0.090 Uiso 0.50 1 calc PR . . H18B H 0.1068 0.5739 0.5349 0.090 Uiso 0.50 1 calc PR . . H18C H 0.2350 0.5170 0.4751 0.090 Uiso 0.50 1 calc PR . . C19 C 0.2385(19) 0.787(2) 0.4690(15) 0.063(7) Uani 0.50 1 d P . . H19A H 0.1839 0.8333 0.5221 0.095 Uiso 0.50 1 calc PR . . H19B H 0.2744 0.8523 0.4171 0.095 Uiso 0.50 1 calc PR . . H19C H 0.3205 0.7392 0.5186 0.095 Uiso 0.50 1 calc PR . . C20 C -0.0140(13) 0.7500 0.3667(11) 0.053(3) Uani 1 2 d S . . H20A H -0.0810 0.6957 0.3079 0.080 Uiso 0.50 1 calc PR . . H20B H -0.0091 0.8410 0.3346 0.080 Uiso 0.50 1 calc PR . . H20C H -0.0483 0.7541 0.4434 0.080 Uiso 0.50 2 calc SPR . . 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 In1 0.0375(4) 0.0552(5) 0.0262(4) 0.000 -0.0023(3) 0.000 O1 0.032(5) 0.063(7) 0.026(4) -0.004(4) -0.001(4) 0.002(5) C1 0.074(12) 0.063(12) 0.049(9) 0.004(9) 0.003(9) 0.002(10) C2 0.055(9) 0.067(10) 0.034(7) -0.008(7) 0.000(6) 0.003(8) C3 0.028(6) 0.046(8) 0.027(6) 0.008(6) -0.001(5) -0.001(6) C4 0.032(6) 0.042(7) 0.029(6) -0.002(5) 0.001(5) 0.003(6) C5 0.036(7) 0.050(8) 0.024(6) -0.003(6) 0.004(5) 0.003(6) C6 0.029(6) 0.037(7) 0.029(6) -0.001(5) -0.007(5) 0.005(5) C7 0.027(6) 0.038(7) 0.032(6) 0.003(5) -0.002(5) 0.002(5) C8 0.032(6) 0.037(7) 0.031(6) -0.004(5) 0.004(5) -0.002(5) C9 0.038(7) 0.054(9) 0.026(6) -0.002(6) 0.002(5) 0.006(6) C10 0.039(8) 0.059(10) 0.056(9) -0.009(8) 0.012(7) -0.005(7) C11 0.055(10) 0.062(11) 0.060(10) 0.009(9) 0.003(8) 0.021(9) C12 0.047(9) 0.103(17) 0.034(9) -0.014(9) 0.006(7) 0.009(11) C13 0.035(7) 0.036(7) 0.028(6) -0.003(6) 0.003(5) -0.003(6) C14 0.12(2) 0.078(16) 0.071(14) -0.028(12) -0.044(14) 0.035(15) C15 0.084(17) 0.20(6) 0.13(2) 0.12(3) -0.060(16) -0.08(2) C16 0.041(9) 0.37(10) 0.054(10) 0.05(3) -0.010(8) -0.01(2) C17 0.038(7) 0.038(7) 0.034(6) 0.001(6) 0.006(5) 0.005(6) C18 0.086(13) 0.051(10) 0.046(9) 0.012(8) 0.022(9) 0.016(10) C19 0.062(9) 0.09(2) 0.044(8) -0.030(9) 0.018(7) -0.016(9) C20 0.045(6) 0.069(8) 0.049(6) 0.000 0.015(5) 0.000 _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 In1 O1 2.047(11) . ? In1 O1 2.047(11) 4_575 ? In1 C1 2.066(19) 4_575 ? In1 C1 2.066(19) . ? In1 C2 2.110(15) . ? In1 C2 2.110(15) 4_575 ? O1 C3 1.345(15) . ? O1 C1 1.37(2) 4_575 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C8 1.405(18) . ? C3 C4 1.424(18) . ? C4 C5 1.413(17) . ? C4 C9 1.535(19) . ? C5 C6 1.383(18) . ? C5 H5 0.9500 . ? C6 C7 1.403(19) . ? C6 C13 1.557(18) . ? C7 C8 1.405(17) . ? C7 H7 0.9500 . ? C8 C17 1.548(18) . ? C9 C12 1.54(2) . ? C9 C10 1.57(2) . ? C9 C11 1.59(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C16 1.45(3) . ? C13 C14 1.48(3) . ? C13 C15 1.53(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.50(2) . ? C17 C19 1.54(2) . ? C17 C20 1.558(17) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 In1 O1 98.8(6) . 4_575 ? O1 In1 C1 38.9(6) . 4_575 ? O1 In1 C1 111.8(6) 4_575 4_575 ? O1 In1 C1 111.8(6) . . ? O1 In1 C1 38.9(6) 4_575 . ? C1 In1 C1 98.3(11) 4_575 . ? O1 In1 C2 137.6(6) . . ? O1 In1 C2 106.3(6) 4_575 . ? C1 In1 C2 141.7(8) 4_575 . ? C1 In1 C2 109.3(8) . . ? O1 In1 C2 106.3(6) . 4_575 ? O1 In1 C2 137.6(6) 4_575 4_575 ? C1 In1 C2 109.3(8) 4_575 4_575 ? C1 In1 C2 141.7(8) . 4_575 ? C2 In1 C2 35.0(10) . 4_575 ? C3 O1 C1 85.6(11) . 4_575 ? C3 O1 In1 117.7(9) . . ? C1 O1 In1 71.3(10) 4_575 . ? In1 C1 H1A 109.5 . . ? In1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? In1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? In1 C2 H2A 109.5 . . ? In1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? In1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O1 C3 C8 120.5(12) . . ? O1 C3 C4 120.3(12) . . ? C8 C3 C4 119.2(11) . . ? C5 C4 C3 118.8(12) . . ? C5 C4 C9 119.7(12) . . ? C3 C4 C9 121.4(11) . . ? C6 C5 C4 122.4(12) . . ? C6 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? C5 C6 C7 117.5(11) . . ? C5 C6 C13 121.7(12) . . ? C7 C6 C13 120.7(12) . . ? C6 C7 C8 122.4(12) . . ? C6 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C7 C8 C3 119.3(12) . . ? C7 C8 C17 119.5(12) . . ? C3 C8 C17 121.1(11) . . ? C4 C9 C12 112.0(12) . . ? C4 C9 C10 113.1(13) . . ? C12 C9 C10 106.9(14) . . ? C4 C9 C11 109.6(12) . . ? C12 C9 C11 104.1(15) . . ? C10 C9 C11 110.8(13) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C16 C13 C14 107(3) . . ? C16 C13 C15 110(3) . . ? C14 C13 C15 109(2) . . ? C16 C13 C6 113.3(13) . . ? C14 C13 C6 110.2(14) . . ? C15 C13 C6 106.5(14) . . ? 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 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C19 109.2(14) . . ? C18 C17 C8 109.6(12) . . ? C19 C17 C8 111.6(12) . . ? C18 C17 C20 109.5(12) . . ? C19 C17 C20 105.0(11) . . ? C8 C17 C20 111.7(10) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.433 _refine_diff_density_min -1.859 _refine_diff_density_rms 0.176 data_gb080573 _database_code_depnum_ccdc_archive 'CCDC 747576' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; Hydrogen atoms were included in calculated positions and refined using a riding model. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H11 In S' _chemical_formula_sum 'C8 H11 In S' _chemical_formula_weight 254.05 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 '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 b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' _symmetry_int_tables_number 61 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' '-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 12.5789(19) _cell_length_b 6.9213(11) _cell_length_c 21.401(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1863.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 198(1) _cell_measurement_reflns_used 4795 _cell_measurement_theta_min 2.498 _cell_measurement_theta_max 28.243 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 2.688 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3467 _exptl_absorpt_correction_T_max 0.8773 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 198(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11723 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2109 _reflns_number_gt 1685 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0213P)^2^+1.5710P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2109 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0219 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0496 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _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 In1 In 0.346661(16) 0.21114(3) 0.473549(9) 0.03096(8) Uani 1 1 d . . . S1 S 0.33345(6) -0.14569(12) 0.43541(3) 0.03145(17) Uani 1 1 d . . . C1 C 0.3117(3) 0.1870(5) 0.57148(14) 0.0401(8) Uani 1 1 d . . . H1A H 0.3481 0.0736 0.5887 0.060 Uiso 1 1 calc R . . H1B H 0.2349 0.1728 0.5773 0.060 Uiso 1 1 calc R . . H1C H 0.3363 0.3034 0.5932 0.060 Uiso 1 1 calc R . . C2 C 0.4784(3) 0.3231(5) 0.42185(16) 0.0458(8) Uani 1 1 d . . . H2A H 0.4703 0.4631 0.4169 0.069 Uiso 1 1 calc R . . H2B H 0.4808 0.2619 0.3806 0.069 Uiso 1 1 calc R . . H2C H 0.5446 0.2956 0.4443 0.069 Uiso 1 1 calc R . . C3 C 0.3395(2) -0.1196(4) 0.35221(13) 0.0287(6) Uani 1 1 d . . . C4 C 0.2521(2) -0.0629(4) 0.31725(13) 0.0342(7) Uani 1 1 d . . . H4 H 0.1862 -0.0371 0.3373 0.041 Uiso 1 1 calc R . . C5 C 0.2611(3) -0.0441(5) 0.25299(15) 0.0416(8) Uani 1 1 d . . . H5 H 0.2012 -0.0051 0.2290 0.050 Uiso 1 1 calc R . . C6 C 0.3565(3) -0.0817(5) 0.22364(14) 0.0426(8) Uani 1 1 d . . . H6 H 0.3623 -0.0679 0.1796 0.051 Uiso 1 1 calc R . . C7 C 0.4433(3) -0.1392(6) 0.25822(15) 0.0448(8) Uani 1 1 d . . . H7 H 0.5088 -0.1664 0.2379 0.054 Uiso 1 1 calc R . . C8 C 0.4353(2) -0.1575(5) 0.32265(14) 0.0392(8) Uani 1 1 d . . . H8 H 0.4955 -0.1960 0.3465 0.047 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 In1 0.03228(12) 0.03489(14) 0.02570(12) 0.00025(9) -0.00038(7) -0.00255(9) S1 0.0358(4) 0.0327(4) 0.0258(4) 0.0007(3) 0.0018(3) -0.0012(3) C1 0.0420(16) 0.051(2) 0.0269(15) -0.0031(15) -0.0041(13) -0.0004(15) C2 0.0355(16) 0.054(2) 0.0474(19) 0.0106(17) 0.0047(14) -0.0058(16) C3 0.0355(15) 0.0255(16) 0.0251(14) -0.0026(12) 0.0026(11) -0.0034(12) C4 0.0389(15) 0.0318(17) 0.0318(15) 0.0013(13) 0.0041(13) 0.0051(14) C5 0.0502(19) 0.0413(19) 0.0333(16) 0.0045(15) -0.0038(14) 0.0055(16) C6 0.057(2) 0.044(2) 0.0262(16) -0.0007(14) 0.0050(14) -0.0050(17) C7 0.0392(17) 0.059(2) 0.0360(17) -0.0022(16) 0.0101(13) -0.0078(17) C8 0.0327(15) 0.052(2) 0.0326(16) -0.0007(15) 0.0018(12) -0.0037(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag In1 C2 2.138(3) . ? In1 C1 2.148(3) . ? In1 S1 2.6041(8) 8_665 ? In1 S1 2.6064(9) . ? S1 C3 1.791(3) . ? S1 In1 2.6041(8) 8_655 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C8 1.386(4) . ? C3 C4 1.387(4) . ? C4 C5 1.386(4) . ? C4 H4 0.9500 . ? C5 C6 1.379(5) . ? C5 H5 0.9500 . ? C6 C7 1.378(5) . ? C6 H6 0.9500 . ? C7 C8 1.388(4) . ? C7 H7 0.9500 . ? C8 H8 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 C2 In1 C1 133.77(13) . . ? C2 In1 S1 111.98(9) . 8_665 ? C1 In1 S1 99.07(9) . 8_665 ? C2 In1 S1 103.34(10) . . ? C1 In1 S1 102.63(10) . . ? S1 In1 S1 101.94(2) 8_665 . ? C3 S1 In1 112.77(9) . 8_655 ? C3 S1 In1 102.29(10) . . ? In1 S1 In1 108.53(3) 8_655 . ? In1 C1 H1A 109.5 . . ? In1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? In1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? In1 C2 H2A 109.5 . . ? In1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? In1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C8 C3 C4 119.8(3) . . ? C8 C3 S1 118.1(2) . . ? C4 C3 S1 122.1(2) . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.0(3) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.1(3) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C3 C8 C7 119.9(3) . . ? C3 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.667 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.092 data_publication_text _database_code_depnum_ccdc_archive 'CCDC 747577' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C20 H35 In S' _chemical_formula_sum 'C20 H35 In S' _exptl_crystal_recrystallization_method Toluene _chemical_melting_point ? _exptl_crystal_description Irregular _exptl_crystal_colour Colourless _diffrn_ambient_temperature 173(1) _chemical_formula_weight 422.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 '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 _chemical_absolute_configuration ? 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 13.1942(13) _cell_length_b 8.9451(9) _cell_length_c 17.4003(17) _cell_angle_alpha 90.00 _cell_angle_beta 91.973(1) _cell_angle_gamma 90.00 _cell_volume 2052.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 8313 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 28.26 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 1.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6688 _exptl_absorpt_correction_T_max 0.8109 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13856 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4611 _reflns_number_gt 4083 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0224P)^2^+1.1730P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4611 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0220 _refine_ls_wR_factor_ref 0.0558 _refine_ls_wR_factor_gt 0.0517 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 In1 In 0.474618(10) 0.701753(15) 0.179279(7) 0.02035(5) Uani 1 1 d . . . S1 S 0.56876(3) 0.47861(5) 0.24223(2) 0.01940(10) Uani 1 1 d . . . C1 C 0.58740(18) 0.8244(3) 0.12020(13) 0.0338(5) Uani 1 1 d . . . H1A H 0.6196 0.7587 0.0831 0.051 Uiso 1 1 calc R . . H1B H 0.6388 0.8617 0.1574 0.051 Uiso 1 1 calc R . . H1C H 0.5555 0.9090 0.0930 0.051 Uiso 1 1 calc R . . C2 C 0.32050(15) 0.6250(2) 0.17277(12) 0.0274(4) Uani 1 1 d . . . H2A H 0.2750 0.7082 0.1840 0.041 Uiso 1 1 calc R . . H2B H 0.3116 0.5450 0.2104 0.041 Uiso 1 1 calc R . . H2C H 0.3045 0.5869 0.1210 0.041 Uiso 1 1 calc R . . C3 C 0.69766(13) 0.5355(2) 0.22808(10) 0.0167(3) Uani 1 1 d . . . C4 C 0.74712(14) 0.6310(2) 0.28302(10) 0.0187(4) Uani 1 1 d . . . C5 C 0.83311(15) 0.7082(2) 0.26032(11) 0.0216(4) Uani 1 1 d . . . H5 H 0.8646 0.7761 0.2957 0.026 Uiso 1 1 calc R . . C6 C 0.87488(14) 0.6908(2) 0.18863(11) 0.0212(4) Uani 1 1 d . . . C7 C 0.83138(14) 0.5837(2) 0.14035(10) 0.0199(4) Uani 1 1 d . . . H7 H 0.8623 0.5645 0.0928 0.024 Uiso 1 1 calc R . . C8 C 0.74477(14) 0.5025(2) 0.15755(10) 0.0179(4) Uani 1 1 d . . . C9 C 0.71521(14) 0.6516(2) 0.36802(10) 0.0206(4) Uani 1 1 d . . . C10 C 0.70986(17) 0.4989(2) 0.40789(11) 0.0273(4) Uani 1 1 d . . . H10A H 0.7752 0.4476 0.4043 0.041 Uiso 1 1 calc R . . H10B H 0.6565 0.4383 0.3827 0.041 Uiso 1 1 calc R . . H10C H 0.6945 0.5131 0.4621 0.041 Uiso 1 1 calc R . . C11 C 0.61308(16) 0.7331(2) 0.37491(11) 0.0264(4) Uani 1 1 d . . . H11A H 0.6047 0.7636 0.4284 0.040 Uiso 1 1 calc R . . H11B H 0.5576 0.6659 0.3589 0.040 Uiso 1 1 calc R . . H11C H 0.6119 0.8218 0.3418 0.040 Uiso 1 1 calc R . . C12 C 0.79402(17) 0.7436(3) 0.41509(11) 0.0288(4) Uani 1 1 d . . . H12A H 0.7743 0.7482 0.4688 0.043 Uiso 1 1 calc R . . H12B H 0.7972 0.8451 0.3941 0.043 Uiso 1 1 calc R . . H12C H 0.8607 0.6961 0.4123 0.043 Uiso 1 1 calc R . . C13 C 0.96397(16) 0.7882(2) 0.16430(12) 0.0280(5) Uani 1 1 d . . . C14 C 0.9208(2) 0.9373(4) 0.1355(2) 0.0775(11) Uani 1 1 d . . . H14A H 0.8857 0.9870 0.1772 0.116 Uiso 1 1 calc R . . H14B H 0.8728 0.9194 0.0923 0.116 Uiso 1 1 calc R . . H14C H 0.9761 1.0011 0.1186 0.116 Uiso 1 1 calc R . . C15 C 1.0384(2) 0.8184(4) 0.23063(15) 0.0522(8) Uani 1 1 d . . . H15A H 1.0634 0.7233 0.2518 0.078 Uiso 1 1 calc R . . H15B H 1.0044 0.8745 0.2707 0.078 Uiso 1 1 calc R . . H15C H 1.0955 0.8770 0.2123 0.078 Uiso 1 1 calc R . . C16 C 1.0214(3) 0.7173(4) 0.0995(2) 0.0792(13) Uani 1 1 d . . . H16A H 1.0772 0.7830 0.0854 0.119 Uiso 1 1 calc R . . H16B H 0.9752 0.7028 0.0547 0.119 Uiso 1 1 calc R . . H16C H 1.0487 0.6204 0.1164 0.119 Uiso 1 1 calc R . . C17 C 0.70849(14) 0.3817(2) 0.09842(10) 0.0209(4) Uani 1 1 d . . . C18 C 0.79109(17) 0.3485(3) 0.04000(12) 0.0301(5) Uani 1 1 d . . . H18A H 0.8544 0.3216 0.0677 0.045 Uiso 1 1 calc R . . H18B H 0.8021 0.4375 0.0085 0.045 Uiso 1 1 calc R . . H18C H 0.7691 0.2654 0.0068 0.045 Uiso 1 1 calc R . . C19 C 0.68897(17) 0.2310(2) 0.13769(12) 0.0277(4) Uani 1 1 d . . . H19A H 0.6308 0.2404 0.1709 0.041 Uiso 1 1 calc R . . H19B H 0.7491 0.2018 0.1687 0.041 Uiso 1 1 calc R . . H19C H 0.6745 0.1546 0.0985 0.041 Uiso 1 1 calc R . . C20 C 0.61339(16) 0.4307(2) 0.05132(11) 0.0278(4) Uani 1 1 d . . . H20A H 0.5955 0.3537 0.0132 0.042 Uiso 1 1 calc R . . H20B H 0.6271 0.5251 0.0250 0.042 Uiso 1 1 calc R . . H20C H 0.5569 0.4446 0.0858 0.042 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 In1 0.01951(8) 0.02141(8) 0.02021(7) 0.00127(5) 0.00161(5) 0.00044(5) S1 0.0155(2) 0.0203(2) 0.0225(2) 0.00372(17) 0.00169(17) -0.00136(18) C1 0.0365(12) 0.0263(11) 0.0398(12) 0.0035(9) 0.0165(10) 0.0003(9) C2 0.0230(10) 0.0279(11) 0.0309(10) -0.0018(8) -0.0032(8) -0.0013(8) C3 0.0137(8) 0.0167(9) 0.0198(8) 0.0022(7) 0.0003(7) 0.0000(7) C4 0.0172(9) 0.0188(9) 0.0199(8) -0.0007(7) -0.0001(7) 0.0034(7) C5 0.0189(9) 0.0215(10) 0.0242(9) -0.0045(7) -0.0014(7) -0.0030(7) C6 0.0157(9) 0.0225(10) 0.0253(9) 0.0011(7) 0.0008(7) -0.0013(7) C7 0.0182(9) 0.0224(10) 0.0191(8) -0.0001(7) 0.0029(7) 0.0004(7) C8 0.0186(9) 0.0175(9) 0.0175(8) 0.0008(7) -0.0012(7) 0.0009(7) C9 0.0199(9) 0.0215(9) 0.0204(8) -0.0020(7) 0.0025(7) 0.0026(8) C10 0.0363(12) 0.0243(10) 0.0213(9) 0.0023(8) 0.0014(8) 0.0043(9) C11 0.0250(10) 0.0281(11) 0.0264(9) -0.0038(8) 0.0044(8) 0.0050(9) C12 0.0288(11) 0.0348(11) 0.0227(9) -0.0076(8) -0.0009(8) 0.0000(9) C13 0.0218(10) 0.0318(12) 0.0307(10) -0.0033(8) 0.0047(8) -0.0091(9) C14 0.0462(17) 0.059(2) 0.127(3) 0.054(2) -0.0036(19) -0.0161(15) C15 0.0365(14) 0.077(2) 0.0427(13) 0.0048(13) -0.0061(11) -0.0336(14) C16 0.0547(19) 0.101(3) 0.085(2) -0.053(2) 0.0474(18) -0.0525(19) C17 0.0224(9) 0.0205(9) 0.0199(8) -0.0022(7) 0.0019(7) -0.0043(8) C18 0.0326(11) 0.0321(11) 0.0261(9) -0.0095(9) 0.0085(9) -0.0049(9) C19 0.0356(12) 0.0204(10) 0.0274(10) -0.0024(8) 0.0067(9) -0.0021(9) C20 0.0310(11) 0.0309(11) 0.0212(9) -0.0016(8) -0.0038(8) -0.0039(9) _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 In1 C1 2.140(2) . ? In1 C2 2.145(2) . ? In1 S1 2.5755(5) . ? In1 S1 2.8948(5) 2_655 ? S1 C3 1.8002(18) . ? S1 In1 2.8948(5) 2_645 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.424(2) . ? C3 C8 1.426(2) . ? C4 C5 1.397(3) . ? C4 C9 1.562(2) . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 C7 1.385(3) . ? C6 C13 1.535(3) . ? C7 C8 1.395(3) . ? C7 H7 0.9500 . ? C8 C17 1.556(2) . ? C9 C10 1.535(3) . ? C9 C12 1.540(3) . ? C9 C11 1.541(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.514(3) . ? C13 C16 1.519(3) . ? C13 C14 1.528(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C19 1.537(3) . ? C17 C20 1.539(3) . ? C17 C18 1.545(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C1 In1 C2 144.30(9) . . ? C1 In1 S1 105.57(7) . . ? C2 In1 S1 102.53(6) . . ? C1 In1 S1 86.56(6) . 2_655 ? C2 In1 S1 95.51(6) . 2_655 ? S1 In1 S1 124.240(8) . 2_655 ? C3 S1 In1 99.61(6) . . ? C3 S1 In1 120.61(6) . 2_645 ? In1 S1 In1 139.764(18) . 2_645 ? In1 C1 H1A 109.5 . . ? In1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? In1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? In1 C2 H2A 109.5 . . ? In1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? In1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C8 119.92(16) . . ? C4 C3 S1 119.41(13) . . ? C8 C3 S1 120.09(13) . . ? C5 C4 C3 117.70(16) . . ? C5 C4 C9 117.24(16) . . ? C3 C4 C9 125.01(16) . . ? C6 C5 C4 123.33(17) . . ? C6 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C7 C6 C5 116.94(17) . . ? C7 C6 C13 122.05(17) . . ? C5 C6 C13 121.00(17) . . ? C6 C7 C8 123.72(16) . . ? C6 C7 H7 118.1 . . ? C8 C7 H7 118.1 . . ? C7 C8 C3 117.49(16) . . ? C7 C8 C17 117.09(15) . . ? C3 C8 C17 125.42(16) . . ? C10 C9 C12 106.03(16) . . ? C10 C9 C11 109.42(16) . . ? C12 C9 C11 106.37(16) . . ? C10 C9 C4 109.96(15) . . ? C12 C9 C4 111.54(16) . . ? C11 C9 C4 113.21(15) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C13 C16 108.3(2) . . ? C15 C13 C14 108.6(2) . . ? C16 C13 C14 108.1(3) . . ? C15 C13 C6 111.95(18) . . ? C16 C13 C6 111.96(19) . . ? C14 C13 C6 107.79(18) . . ? 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 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C19 C17 C20 109.91(16) . . ? C19 C17 C18 104.87(16) . . ? C20 C17 C18 106.57(15) . . ? C19 C17 C8 111.56(15) . . ? C20 C17 C8 112.41(16) . . ? C18 C17 C8 111.15(15) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.530 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.067 data_gb080685 _database_code_depnum_ccdc_archive 'CCDC 747578' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; Hydrogen atoms were included in calculated positions and refined using a riding model. The compound is a racemate. The Flack parameter is therfor meaningless and has been removed from the cif. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 In2 Se2' _chemical_formula_sum 'C16 H22 In2 Se2' _chemical_formula_weight 601.90 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 '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 c' _symmetry_space_group_name_Hall 'P -2yc' _symmetry_int_tables_number 7 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 10.9188(15) _cell_length_b 11.7444(17) _cell_length_c 7.7891(11) _cell_angle_alpha 90.00 _cell_angle_beta 108.046(2) _cell_angle_gamma 90.00 _cell_volume 949.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 4318 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.22 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.105 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 6.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.327026 _exptl_absorpt_correction_T_max 0.730296 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6387 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3694 _reflns_number_gt 3479 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0279P)^2^+18.6515P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3694 _refine_ls_number_parameters 185 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 In1 In 0.57566(8) 0.16178(10) 0.83523(12) 0.0268(3) Uani 1 1 d . . . In2 In 0.55866(8) 0.34299(11) 0.42236(12) 0.0282(3) Uani 1 1 d . . . Se1 Se 0.65852(14) 0.38037(13) 0.7868(2) 0.0230(3) Uani 1 1 d . . . Se2 Se 0.47128(15) 0.12775(15) 0.4749(2) 0.0271(4) Uani 1 1 d . . . C1 C 0.7431(19) 0.0507(14) 0.890(3) 0.034(4) Uani 1 1 d . . . H1A H 0.7872 0.0483 1.0203 0.052 Uiso 1 1 calc R . . H1B H 0.8021 0.0800 0.8280 0.052 Uiso 1 1 calc R . . H1C H 0.7153 -0.0262 0.8463 0.052 Uiso 1 1 calc R . . C2 C 0.4353(17) 0.2053(17) 0.959(2) 0.033(4) Uani 1 1 d . . . H2A H 0.4233 0.1415 1.0332 0.049 Uiso 1 1 calc R . . H2B H 0.3536 0.2220 0.8656 0.049 Uiso 1 1 calc R . . H2C H 0.4638 0.2726 1.0352 0.049 Uiso 1 1 calc R . . C3 C 0.7209(15) 0.2913(15) 0.338(3) 0.034(4) Uani 1 1 d . . . H3A H 0.6990 0.2990 0.2070 0.051 Uiso 1 1 calc R . . H3B H 0.7422 0.2118 0.3726 0.051 Uiso 1 1 calc R . . H3C H 0.7952 0.3397 0.3971 0.051 Uiso 1 1 calc R . . C4 C 0.3899(17) 0.4446(17) 0.323(3) 0.036(4) Uani 1 1 d . . . H4A H 0.4006 0.4971 0.2305 0.054 Uiso 1 1 calc R . . H4B H 0.3760 0.4883 0.4222 0.054 Uiso 1 1 calc R . . H4C H 0.3155 0.3953 0.2693 0.054 Uiso 1 1 calc R . . C5 C 0.8423(17) 0.3718(15) 0.816(3) 0.027(4) Uani 1 1 d . . . C6 C 0.8947(12) 0.4500(11) 0.7276(17) 0.028(3) Uani 1 1 d . . . H6 H 0.8404 0.5035 0.6480 0.034 Uiso 1 1 calc R . . C7 C 1.0253(13) 0.4510(13) 0.7537(19) 0.035(3) Uani 1 1 d . . . H7 H 1.0614 0.5027 0.6887 0.042 Uiso 1 1 calc R . . C8 C 1.1031(18) 0.3757(14) 0.876(3) 0.034(5) Uani 1 1 d . . . H8 H 1.1936 0.3790 0.8986 0.041 Uiso 1 1 calc R . . C9 C 1.0533(13) 0.2962(14) 0.966(2) 0.037(3) Uani 1 1 d . . . H9 H 1.1078 0.2414 1.0418 0.045 Uiso 1 1 calc R . . C10 C 0.9202(11) 0.2976(11) 0.9422(18) 0.028(3) Uani 1 1 d . . . H10 H 0.8844 0.2487 1.0112 0.033 Uiso 1 1 calc R . . C11 C 0.2879(17) 0.1319(15) 0.426(3) 0.024(3) Uani 1 1 d . . . C12 C 0.2142(12) 0.0506(11) 0.3175(18) 0.030(3) Uani 1 1 d . . . H12 H 0.2544 -0.0034 0.2617 0.036 Uiso 1 1 calc R . . C13 C 0.0800(14) 0.0440(14) 0.285(2) 0.041(4) Uani 1 1 d . . . H13 H 0.0307 -0.0165 0.2170 0.049 Uiso 1 1 calc R . . C14 C 0.0209(17) 0.1313(18) 0.359(3) 0.035(4) Uani 1 1 d . . . H14 H -0.0693 0.1302 0.3404 0.042 Uiso 1 1 calc R . . C15 C 0.0956(13) 0.2167(13) 0.458(2) 0.037(3) Uani 1 1 d . . . H15 H 0.0554 0.2768 0.5021 0.045 Uiso 1 1 calc R . . C16 C 0.2265(12) 0.2178(12) 0.4946(19) 0.031(3) Uani 1 1 d . . . H16 H 0.2761 0.2769 0.5669 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 In1 0.0232(6) 0.0296(6) 0.0285(7) 0.0004(5) 0.0091(5) -0.0013(5) In2 0.0199(5) 0.0306(6) 0.0308(7) -0.0016(5) 0.0028(5) 0.0068(5) Se1 0.0143(6) 0.0212(7) 0.0328(10) -0.0027(7) 0.0064(6) -0.0011(6) Se2 0.0264(8) 0.0254(8) 0.0270(10) -0.0033(7) 0.0044(7) 0.0018(7) C1 0.043(9) 0.028(7) 0.030(9) 0.005(6) 0.007(7) 0.007(7) C2 0.029(8) 0.048(9) 0.020(7) -0.006(7) 0.005(6) -0.007(7) C3 0.010(6) 0.031(8) 0.058(12) -0.013(7) 0.005(7) 0.007(5) C4 0.023(7) 0.052(10) 0.039(10) 0.011(8) 0.018(7) 0.011(7) C5 0.020(7) 0.029(8) 0.025(9) -0.012(7) -0.003(6) 0.001(6) C6 0.033(6) 0.028(6) 0.022(6) 0.006(5) 0.007(5) 0.006(5) C7 0.038(7) 0.044(8) 0.027(7) -0.003(6) 0.016(6) -0.011(6) C8 0.020(7) 0.015(7) 0.062(13) -0.006(7) 0.004(7) 0.000(5) C9 0.026(6) 0.046(8) 0.035(8) 0.004(6) 0.002(6) 0.007(6) C10 0.023(6) 0.025(6) 0.029(7) 0.010(5) 0.000(5) -0.006(5) C11 0.018(7) 0.031(8) 0.026(8) 0.005(6) 0.013(7) -0.001(6) C12 0.031(6) 0.024(6) 0.032(7) -0.013(5) 0.006(5) 0.003(5) C13 0.033(7) 0.045(8) 0.040(9) -0.013(7) 0.006(6) -0.016(6) C14 0.016(7) 0.045(10) 0.044(11) 0.000(8) 0.011(7) 0.003(7) C15 0.031(7) 0.043(8) 0.039(8) -0.007(6) 0.013(6) 0.008(6) C16 0.029(6) 0.033(7) 0.032(7) -0.006(6) 0.009(5) -0.005(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 In1 C2 2.110(19) . ? In1 C1 2.178(18) . ? In1 Se2 2.712(2) . ? In1 Se1 2.786(2) . ? In2 C4 2.130(18) . ? In2 C3 2.157(17) . ? In2 Se1 2.742(2) . ? In2 Se2 2.777(2) . ? Se1 C5 1.951(19) . ? Se2 C11 1.920(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.38(2) . ? C5 C10 1.39(2) . ? C6 C7 1.377(19) . ? C6 H6 0.9500 . ? C7 C8 1.38(2) . ? C7 H7 0.9500 . ? C8 C9 1.37(3) . ? C8 H8 0.9500 . ? C9 C10 1.408(17) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.36(2) . ? C11 C16 1.41(2) . ? C12 C13 1.411(18) . ? C12 H12 0.9500 . ? C13 C14 1.42(3) . ? C13 H13 0.9500 . ? C14 C15 1.37(3) . ? C14 H14 0.9500 . ? C15 C16 1.368(18) . ? C15 H15 0.9500 . ? C16 H16 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 C2 In1 C1 137.7(7) . . ? C2 In1 Se2 112.1(5) . . ? C1 In1 Se2 99.9(5) . . ? C2 In1 Se1 98.7(5) . . ? C1 In1 Se1 106.9(5) . . ? Se2 In1 Se1 92.61(7) . . ? C4 In2 C3 138.2(7) . . ? C4 In2 Se1 108.0(5) . . ? C3 In2 Se1 105.0(5) . . ? C4 In2 Se2 105.4(5) . . ? C3 In2 Se2 98.1(5) . . ? Se1 In2 Se2 92.16(7) . . ? C5 Se1 In2 100.3(6) . . ? C5 Se1 In1 107.6(5) . . ? In2 Se1 In1 87.19(6) . . ? C11 Se2 In1 106.3(6) . . ? C11 Se2 In2 109.4(5) . . ? In1 Se2 In2 88.00(7) . . ? In1 C1 H1A 109.5 . . ? In1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? In1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? In1 C2 H2A 109.5 . . ? In1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? In1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? In2 C3 H3A 109.5 . . ? In2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? In2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? In2 C4 H4A 109.5 . . ? In2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? In2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 121.0(15) . . ? C6 C5 Se1 118.6(12) . . ? C10 C5 Se1 119.9(14) . . ? C5 C6 C7 120.3(13) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C8 118.9(14) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C9 C8 C7 122.0(16) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 118.8(14) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C5 C10 C9 118.7(14) . . ? C5 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C12 C11 C16 118.7(14) . . ? C12 C11 Se2 119.1(13) . . ? C16 C11 Se2 122.2(13) . . ? C11 C12 C13 122.0(13) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C12 C13 C14 117.7(13) . . ? C12 C13 H13 121.1 . . ? C14 C13 H13 121.1 . . ? C15 C14 C13 119.2(15) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 121.8(14) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C15 C16 C11 120.2(13) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.920 _refine_diff_density_min -1.107 _refine_diff_density_rms 0.236 data_gb080709 _database_code_depnum_ccdc_archive 'CCDC 747579' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; Hydrogen atoms were included in calculated positions and refined using a riding model. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H17 In Se' _chemical_formula_sum 'C11 H17 In Se' _chemical_formula_weight 343.03 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 '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 c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac ' _symmetry_int_tables_number 29 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 22.591(3) _cell_length_b 7.2214(9) _cell_length_c 7.5586(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1233.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 198(1) _cell_measurement_reflns_used 5684 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 28.13 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.575 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.010 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 4.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1679 _exptl_absorpt_correction_T_max 0.9533 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 198(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7769 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2314 _reflns_number_gt 2083 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0284P)^2^] 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 0.035(13) _refine_ls_number_reflns 2314 _refine_ls_number_parameters 123 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0606 _refine_ls_wR_factor_gt 0.0589 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 In1 In 0.014654(13) 0.19282(4) 0.08684(5) 0.02579(9) Uani 1 1 d . . . Se1 Se 0.049247(19) 0.07267(6) 0.41390(7) 0.02615(11) Uani 1 1 d . . . C1 C -0.0492(2) 0.3972(8) 0.1638(8) 0.0369(13) Uani 1 1 d . . . H1A H -0.0425 0.5113 0.0966 0.055 Uiso 1 1 calc R . . H1B H -0.0452 0.4229 0.2906 0.055 Uiso 1 1 calc R . . H1C H -0.0892 0.3508 0.1395 0.055 Uiso 1 1 calc R . . C2 C 0.0982(2) 0.1857(8) -0.0469(7) 0.0388(13) Uani 1 1 d . . . H2A H 0.0920 0.2024 -0.1742 0.058 Uiso 1 1 calc R . . H2B H 0.1174 0.0660 -0.0256 0.058 Uiso 1 1 calc R . . H2C H 0.1235 0.2854 -0.0020 0.058 Uiso 1 1 calc R . . C3 C 0.1254(2) -0.0364(6) 0.3615(6) 0.0214(9) Uani 1 1 d . . . C4 C 0.1304(2) -0.2088(6) 0.2734(6) 0.0259(10) Uani 1 1 d . . . C5 C 0.1865(2) -0.2833(7) 0.2467(7) 0.0297(11) Uani 1 1 d . . . H5 H 0.1900 -0.4012 0.1919 0.036 Uiso 1 1 calc R . . C6 C 0.2375(3) -0.1910(7) 0.2977(6) 0.0317(12) Uani 1 1 d . . . C7 C 0.2322(2) -0.0196(6) 0.3767(7) 0.0305(11) Uani 1 1 d . . . H7 H 0.2670 0.0465 0.4086 0.037 Uiso 1 1 calc R . . C8 C 0.1767(2) 0.0591(6) 0.4111(8) 0.0272(9) Uani 1 1 d . . . C9 C 0.0777(3) -0.3140(7) 0.2047(8) 0.0369(13) Uani 1 1 d . . . H9A H 0.0902 -0.3963 0.1086 0.055 Uiso 1 1 calc R . . H9B H 0.0481 -0.2265 0.1602 0.055 Uiso 1 1 calc R . . H9C H 0.0605 -0.3878 0.3006 0.055 Uiso 1 1 calc R . . C10 C 0.2971(3) -0.2778(8) 0.2691(9) 0.0432(14) Uani 1 1 d . . . H10A H 0.2958 -0.4080 0.3055 0.065 Uiso 1 1 calc R . . H10B H 0.3268 -0.2119 0.3395 0.065 Uiso 1 1 calc R . . H10C H 0.3076 -0.2702 0.1435 0.065 Uiso 1 1 calc R . . C11 C 0.1751(3) 0.2478(7) 0.4968(8) 0.0375(13) Uani 1 1 d . . . H11A H 0.1491 0.3297 0.4288 0.056 Uiso 1 1 calc R . . H11B H 0.2152 0.2999 0.4993 0.056 Uiso 1 1 calc R . . H11C H 0.1601 0.2365 0.6180 0.056 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 In1 0.02072(15) 0.02925(14) 0.02741(15) 0.00137(17) 0.00109(18) 0.00267(13) Se1 0.0239(2) 0.0298(2) 0.0248(2) 0.0018(2) 0.0018(2) 0.0038(2) C1 0.029(3) 0.037(3) 0.045(3) -0.001(2) 0.005(2) 0.005(3) C2 0.029(3) 0.052(3) 0.036(3) 0.010(2) 0.006(2) 0.000(3) C3 0.021(2) 0.023(2) 0.020(2) 0.0029(16) -0.0001(18) 0.0012(19) C4 0.030(3) 0.030(2) 0.017(2) -0.0014(18) -0.001(2) 0.004(2) C5 0.031(3) 0.033(2) 0.026(3) 0.000(2) 0.003(3) 0.003(2) C6 0.031(3) 0.044(3) 0.020(3) 0.001(2) 0.003(2) 0.006(3) C7 0.024(3) 0.040(3) 0.028(3) 0.0014(18) 0.001(2) -0.003(2) C8 0.024(2) 0.033(2) 0.024(2) 0.002(2) 0.001(3) -0.005(2) C9 0.032(3) 0.041(3) 0.038(3) -0.016(2) 0.000(3) 0.001(3) C10 0.032(3) 0.059(4) 0.039(3) 0.004(3) 0.001(3) 0.009(3) C11 0.035(3) 0.034(2) 0.044(3) -0.006(2) 0.006(3) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag In1 C2 2.142(5) . ? In1 C1 2.145(5) . ? In1 Se1 2.7328(6) 2_554 ? In1 Se1 2.7340(7) . ? Se1 C3 1.934(5) . ? Se1 In1 2.7328(6) 2 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C8 1.399(6) . ? C3 C4 1.417(6) . ? C4 C5 1.391(7) . ? C4 C9 1.506(7) . ? C5 C6 1.385(7) . ? C5 H5 0.9500 . ? C6 C7 1.379(7) . ? C6 C10 1.501(8) . ? C7 C8 1.401(7) . ? C7 H7 0.9500 . ? C8 C11 1.510(7) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 In1 C1 137.5(2) . . ? C2 In1 Se1 102.88(15) . 2_554 ? C1 In1 Se1 104.90(16) . 2_554 ? C2 In1 Se1 99.62(15) . . ? C1 In1 Se1 99.52(16) . . ? Se1 In1 Se1 111.154(15) 2_554 . ? C3 Se1 In1 106.39(12) . 2 ? C3 Se1 In1 101.46(12) . . ? In1 Se1 In1 120.274(19) 2 . ? In1 C1 H1A 109.5 . . ? In1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? In1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? In1 C2 H2A 109.5 . . ? In1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? In1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C8 C3 C4 119.5(4) . . ? C8 C3 Se1 118.8(3) . . ? C4 C3 Se1 121.7(4) . . ? C5 C4 C3 118.7(5) . . ? C5 C4 C9 118.4(4) . . ? C3 C4 C9 122.9(4) . . ? C6 C5 C4 122.0(5) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C7 C6 C5 118.7(5) . . ? C7 C6 C10 121.0(5) . . ? C5 C6 C10 120.3(4) . . ? C6 C7 C8 121.4(5) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C3 C8 C7 119.5(4) . . ? C3 C8 C11 122.7(4) . . ? C7 C8 C11 117.8(4) . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.456 _refine_diff_density_min -0.874 _refine_diff_density_rms 0.123 data_gb090598 _database_code_depnum_ccdc_archive 'CCDC 747580' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; Hydrogen atoms were included in calculated positions and refined using a riding model. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C20 H35 In Se' _chemical_formula_sum 'C20 H35 In Se' _exptl_crystal_recrystallization_method Toluene _chemical_melting_point ? _exptl_crystal_description Rod _exptl_crystal_colour Colourless _diffrn_ambient_temperature 173(1) _chemical_formula_weight 469.26 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 '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 _chemical_absolute_configuration ? 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 13.226(3) _cell_length_b 9.016(2) _cell_length_c 17.484(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.547(4) _cell_angle_gamma 90.00 _cell_volume 2082.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 7165 _cell_measurement_theta_min 2.332 _cell_measurement_theta_max 27.983 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 2.879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2770 _exptl_absorpt_correction_T_max 0.8130 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8755 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4570 _reflns_number_gt 3491 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0572P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4570 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.404 _refine_ls_restrained_S_all 1.404 _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 In1 In 0.47039(3) 0.79115(4) 0.17196(2) 0.01993(12) Uani 1 1 d . . . Se1 Se 0.56285(4) 1.01834(6) 0.24488(3) 0.01924(14) Uani 1 1 d . . . C1 C 0.5848(5) 0.6819(7) 0.1107(3) 0.0356(16) Uani 1 1 d . . . H1A H 0.5593 0.5859 0.0920 0.053 Uiso 1 1 calc R . . H1B H 0.6447 0.6663 0.1448 0.053 Uiso 1 1 calc R . . H1C H 0.6031 0.7434 0.0672 0.053 Uiso 1 1 calc R . . C2 C 0.3165(4) 0.8636(6) 0.1643(3) 0.0272(13) Uani 1 1 d . . . H2A H 0.3013 0.9063 0.1135 0.041 Uiso 1 1 calc R . . H2B H 0.3059 0.9388 0.2036 0.041 Uiso 1 1 calc R . . H2C H 0.2717 0.7790 0.1722 0.041 Uiso 1 1 calc R . . C3 C 0.7027(4) 0.9618(6) 0.2296(3) 0.0168(11) Uani 1 1 d . . . C4 C 0.7515(4) 0.8640(6) 0.2829(3) 0.0179(11) Uani 1 1 d . . . C5 C 0.8362(4) 0.7873(6) 0.2590(3) 0.0207(11) Uani 1 1 d . . . H5 H 0.8680 0.7179 0.2931 0.025 Uiso 1 1 calc R . . C6 C 0.8762(4) 0.8080(6) 0.1872(3) 0.0186(12) Uani 1 1 d . . . C7 C 0.8332(4) 0.9168(6) 0.1413(3) 0.0198(12) Uani 1 1 d . . . H7 H 0.8633 0.9379 0.0941 0.024 Uiso 1 1 calc R . . C8 C 0.7479(4) 0.9983(6) 0.1600(3) 0.0165(11) Uani 1 1 d . . . C9 C 0.7222(4) 0.8389(6) 0.3677(3) 0.0206(12) Uani 1 1 d . . . C10 C 0.8035(5) 0.7488(6) 0.4128(3) 0.0279(14) Uani 1 1 d . . . H10A H 0.8697 0.7957 0.4077 0.042 Uiso 1 1 calc R . . H10B H 0.8052 0.6476 0.3925 0.042 Uiso 1 1 calc R . . H10C H 0.7874 0.7458 0.4669 0.042 Uiso 1 1 calc R . . C11 C 0.6225(4) 0.7538(6) 0.3743(3) 0.0255(13) Uani 1 1 d . . . H11A H 0.6155 0.7223 0.4275 0.038 Uiso 1 1 calc R . . H11B H 0.6226 0.6663 0.3411 0.038 Uiso 1 1 calc R . . H11C H 0.5656 0.8182 0.3587 0.038 Uiso 1 1 calc R . . C12 C 0.7163(5) 0.9877(6) 0.4093(3) 0.0283(14) Uani 1 1 d . . . H12A H 0.7801 1.0417 0.4046 0.042 Uiso 1 1 calc R . . H12B H 0.7047 0.9703 0.4635 0.042 Uiso 1 1 calc R . . H12C H 0.6604 1.0465 0.3865 0.042 Uiso 1 1 calc R . . C13 C 0.9641(4) 0.7109(6) 0.1618(3) 0.0264(13) Uani 1 1 d . . . C14 C 0.9202(6) 0.5637(9) 0.1340(5) 0.072(3) Uani 1 1 d . . . H14A H 0.8711 0.5813 0.0913 0.108 Uiso 1 1 calc R . . H14B H 0.8863 0.5149 0.1759 0.108 Uiso 1 1 calc R . . H14C H 0.9748 0.5001 0.1169 0.108 Uiso 1 1 calc R . . C15 C 1.0409(5) 0.6827(9) 0.2272(4) 0.051(2) Uani 1 1 d . . . H15A H 1.0959 0.6209 0.2091 0.077 Uiso 1 1 calc R . . H15B H 1.0079 0.6315 0.2688 0.077 Uiso 1 1 calc R . . H15C H 1.0685 0.7775 0.2460 0.077 Uiso 1 1 calc R . . C16 C 1.0189(5) 0.7812(9) 0.0965(4) 0.063(3) Uani 1 1 d . . . H16A H 1.0754 0.7175 0.0829 0.094 Uiso 1 1 calc R . . H16B H 1.0449 0.8787 0.1124 0.094 Uiso 1 1 calc R . . H16C H 0.9719 0.7927 0.0520 0.094 Uiso 1 1 calc R . . C17 C 0.7122(4) 1.1227(6) 0.1028(3) 0.0204(12) Uani 1 1 d . . . C18 C 0.7956(5) 1.1596(7) 0.0467(3) 0.0303(14) Uani 1 1 d . . . H18A H 0.8048 1.0753 0.0123 0.045 Uiso 1 1 calc R . . H18B H 0.8593 1.1797 0.0757 0.045 Uiso 1 1 calc R . . H18C H 0.7758 1.2473 0.0165 0.045 Uiso 1 1 calc R . . C19 C 0.6928(5) 1.2688(6) 0.1447(3) 0.0269(14) Uani 1 1 d . . . H19A H 0.6846 1.3493 0.1073 0.040 Uiso 1 1 calc R . . H19B H 0.7503 1.2906 0.1802 0.040 Uiso 1 1 calc R . . H19C H 0.6310 1.2597 0.1734 0.040 Uiso 1 1 calc R . . C20 C 0.6186(4) 1.0773(6) 0.0539(3) 0.0282(13) Uani 1 1 d . . . H20A H 0.5617 1.0611 0.0869 0.042 Uiso 1 1 calc R . . H20B H 0.6328 0.9855 0.0263 0.042 Uiso 1 1 calc R . . H20C H 0.6013 1.1562 0.0170 0.042 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 In1 0.0221(2) 0.0178(2) 0.0200(2) -0.00085(16) 0.00158(15) -0.00090(17) Se1 0.0165(3) 0.0172(3) 0.0242(3) -0.0049(2) 0.0017(2) 0.0014(2) C1 0.045(4) 0.023(4) 0.040(3) -0.004(3) 0.018(3) 0.000(3) C2 0.024(3) 0.025(3) 0.032(3) 0.003(3) -0.005(3) 0.000(3) C3 0.015(3) 0.013(3) 0.023(3) -0.004(2) 0.004(2) -0.001(2) C4 0.021(3) 0.015(3) 0.017(2) 0.000(2) -0.001(2) -0.004(2) C5 0.022(3) 0.017(3) 0.023(3) 0.004(2) -0.003(2) 0.002(2) C6 0.019(3) 0.016(3) 0.021(3) -0.001(2) -0.001(2) 0.000(2) C7 0.020(3) 0.019(3) 0.021(3) 0.001(2) 0.003(2) 0.000(2) C8 0.015(3) 0.014(3) 0.020(3) 0.001(2) -0.002(2) -0.001(2) C9 0.026(3) 0.017(3) 0.019(3) 0.001(2) 0.000(2) -0.001(2) C10 0.032(3) 0.030(4) 0.022(3) 0.009(2) -0.003(3) 0.002(3) C11 0.028(3) 0.024(3) 0.025(3) 0.005(2) 0.005(3) -0.004(2) C12 0.041(4) 0.023(3) 0.021(3) 0.001(2) -0.001(3) -0.005(3) C13 0.022(3) 0.027(3) 0.030(3) 0.000(3) 0.002(2) 0.007(3) C14 0.050(5) 0.051(5) 0.116(7) -0.045(5) 0.008(5) 0.011(4) C15 0.039(4) 0.072(6) 0.043(4) -0.003(4) 0.001(3) 0.029(4) C16 0.041(5) 0.079(6) 0.070(5) 0.029(4) 0.035(4) 0.037(4) C17 0.023(3) 0.016(3) 0.023(3) 0.003(2) 0.001(2) 0.003(2) C18 0.037(4) 0.027(3) 0.027(3) 0.012(3) 0.008(3) 0.006(3) C19 0.037(4) 0.020(3) 0.024(3) 0.005(2) 0.004(3) -0.001(3) C20 0.034(3) 0.029(3) 0.021(3) 0.002(2) -0.004(2) 0.004(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 In1 C1 2.134(5) . ? In1 C2 2.136(5) . ? In1 Se1 2.6792(8) . ? In1 Se1 2.9007(8) 2_645 ? Se1 C3 1.948(5) . ? Se1 In1 2.9007(8) 2_655 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.418(7) . ? C3 C8 1.419(6) . ? C4 C5 1.397(7) . ? C4 C9 1.565(6) . ? C5 C6 1.396(6) . ? C5 H5 0.9500 . ? C6 C7 1.375(7) . ? C6 C13 1.536(7) . ? C7 C8 1.397(7) . ? C7 H7 0.9500 . ? C8 C17 1.561(7) . ? C9 C12 1.530(7) . ? C9 C11 1.535(7) . ? C9 C10 1.537(8) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.517(8) . ? C13 C16 1.519(7) . ? C13 C14 1.520(9) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C20 1.529(7) . ? C17 C19 1.535(7) . ? C17 C18 1.545(7) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C1 In1 C2 143.6(2) . . ? C1 In1 Se1 105.82(18) . . ? C2 In1 Se1 102.10(16) . . ? C1 In1 Se1 89.25(16) . 2_645 ? C2 In1 Se1 97.22(15) . 2_645 ? Se1 In1 Se1 119.07(2) . 2_645 ? C3 Se1 In1 98.66(15) . . ? C3 Se1 In1 117.18(15) . 2_655 ? In1 Se1 In1 144.16(2) . 2_655 ? In1 C1 H1A 109.5 . . ? In1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? In1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? In1 C2 H2A 109.5 . . ? In1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? In1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C8 120.8(5) . . ? C4 C3 Se1 118.7(3) . . ? C8 C3 Se1 119.7(4) . . ? C5 C4 C3 117.3(4) . . ? C5 C4 C9 116.6(5) . . ? C3 C4 C9 126.0(4) . . ? C6 C5 C4 123.0(5) . . ? C6 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C7 C6 C5 117.2(5) . . ? C7 C6 C13 122.5(4) . . ? C5 C6 C13 120.3(5) . . ? C6 C7 C8 123.8(4) . . ? C6 C7 H7 118.1 . . ? C8 C7 H7 118.1 . . ? C7 C8 C3 117.0(5) . . ? C7 C8 C17 116.9(4) . . ? C3 C8 C17 126.1(4) . . ? C12 C9 C11 109.9(4) . . ? C12 C9 C10 105.6(5) . . ? C11 C9 C10 106.3(4) . . ? C12 C9 C4 110.1(4) . . ? C11 C9 C4 113.2(4) . . ? C10 C9 C4 111.4(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C13 C16 108.1(5) . . ? C15 C13 C14 109.2(6) . . ? C16 C13 C14 108.2(6) . . ? C15 C13 C6 111.6(5) . . ? C16 C13 C6 111.9(5) . . ? C14 C13 C6 107.9(5) . . ? 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 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C20 C17 C19 110.4(5) . . ? C20 C17 C18 106.6(4) . . ? C19 C17 C18 104.9(4) . . ? C20 C17 C8 112.4(4) . . ? C19 C17 C8 111.3(4) . . ? C18 C17 C8 110.9(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.185 _refine_diff_density_min -1.208 _refine_diff_density_rms 0.137