# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_12aj002k _database_code_depnum_ccdc_archive 'CCDC 909373' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-09-13 _audit_author_name 'Webster, M.' _chemical_name_systematic ; dibromo(dimethyl sulfide)selenium(II) ; # Me2S = C2H6S # dimethyl sulphide # methylsulfanylmethane (chemspider) # dimethyl sulfide (ACD iLab (defaults)) _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H6 Br2 S Se' _chemical_formula_sum 'C2 H6 Br2 S Se' _chemical_formula_weight 300.91 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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' 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 6.518(4) _cell_length_b 6.8952(9) _cell_length_c 16.170(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.587(11) _cell_angle_gamma 90.00 _cell_volume 714.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2799 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 16.613 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.105 # Expt'l Tmin & Tmax _exptl_absorpt_correction_T_max 1.000 # scaled to Tmax=1.0 _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, HF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ SuperBright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3254 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.1151 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1435 _reflns_number_gt 959 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.0000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1435 _refine_ls_number_parameters 57 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0517 _refine_ls_wR_factor_gt 0.0498 _refine_ls_goodness_of_fit_ref 0.679 _refine_ls_restrained_S_all 0.679 _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 Se1 Se 0.33187(8) 1.09064(8) 0.32794(4) 0.00902(15) Uani 1 1 d . . . Br1 Br 0.37500(8) 0.95843(8) 0.17236(4) 0.01314(15) Uani 1 1 d . . . Br2 Br 0.28124(8) 1.20763(8) 0.46549(4) 0.01289(15) Uani 1 1 d . . . S1 S 0.1059(2) 0.8413(2) 0.32494(9) 0.0123(3) Uani 1 1 d . . . C1 C -0.1340(8) 0.9524(8) 0.3382(4) 0.0153(14) Uani 1 1 d . . . H1A H -0.2349 0.8517 0.3459 0.023 Uiso 1 1 calc R . . H1B H -0.1898 1.0294 0.2882 0.023 Uiso 1 1 calc R . . H1C H -0.1087 1.0369 0.3878 0.023 Uiso 1 1 calc R . . C2 C 0.1787(8) 0.7123(8) 0.4221(4) 0.0181(15) Uani 1 1 d . . . H2A H 0.1894 0.8034 0.4693 0.027 Uiso 1 1 calc R . . H2B H 0.3138 0.6489 0.4235 0.027 Uiso 1 1 calc R . . H2C H 0.0727 0.6142 0.4268 0.027 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 Se1 0.0065(3) 0.0099(3) 0.0110(3) 0.0005(2) 0.0024(2) -0.0001(2) Br1 0.0138(3) 0.0138(3) 0.0127(3) 0.0003(3) 0.0048(3) 0.0034(3) Br2 0.0155(3) 0.0124(3) 0.0112(3) -0.0010(3) 0.0039(3) 0.0002(3) S1 0.0105(8) 0.0122(8) 0.0151(8) -0.0025(7) 0.0048(7) -0.0015(7) C1 0.007(3) 0.020(3) 0.019(4) 0.007(3) 0.004(3) -0.005(3) C2 0.013(3) 0.011(3) 0.029(4) 0.009(3) 0.001(3) 0.002(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 Se1 S1 2.2587(16) . ? Se1 Br2 2.4448(8) . ? Se1 Br1 2.7384(9) . ? S1 C1 1.789(5) . ? S1 C2 1.792(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 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 S1 Se1 Br2 94.25(4) . . ? S1 Se1 Br1 84.46(4) . . ? Br2 Se1 Br1 178.16(3) . . ? C1 S1 C2 101.7(3) . . ? C1 S1 Se1 104.6(2) . . ? C2 S1 Se1 107.00(19) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Se1 Br1 3.176(1) . 2_655 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.885 _refine_diff_density_min -0.750 _refine_diff_density_rms 0.198 data_12aj011r _database_code_depnum_ccdc_archive 'CCDC 909374' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-09-14 _audit_author_name 'Webster, M.' _chemical_name_systematic ; trans-dichlorobis(tetrahydrothiophene)selenium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H16 Cl2 S2 Se' _chemical_formula_sum 'C8 H16 Cl2 S2 Se' _chemical_formula_weight 326.19 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' Cl Cl 0.1484 0.1585 '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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.591(6) _cell_length_b 9.133(3) _cell_length_c 9.089(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.820(8) _cell_angle_gamma 90.00 _cell_volume 1209.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2738 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.4 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 3.846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.662 # Expt'l Tmin & Tmax _exptl_absorpt_correction_T_max 1.000 # scaled to Tmax=1.0 _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, VHF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ Superbright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 ' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2996 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1377 _reflns_number_gt 1208 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.0192P)^2^+2.0751P] 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 1377 _refine_ls_number_parameters 61 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0538 _refine_ls_wR_factor_gt 0.0519 _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 Se1 Se 0.5000 0.0000 0.5000 0.01000(9) Uani 1 2 d S . . Cl1 Cl 0.40014(4) 0.18784(6) 0.34245(6) 0.01565(13) Uani 1 1 d . . . S1 S 0.64957(4) 0.14334(6) 0.57399(6) 0.01270(13) Uani 1 1 d . . . C1 C 0.61763(16) 0.3338(2) 0.5218(3) 0.0139(5) Uani 1 1 d . . . H1A H 0.6705 0.3901 0.5157 0.017 Uiso 1 1 calc R . . H1B H 0.5667 0.3400 0.4189 0.017 Uiso 1 1 calc R . . C2 C 0.58787(15) 0.3924(3) 0.6528(3) 0.0154(5) Uani 1 1 d . . . H2A H 0.5253 0.3580 0.6389 0.018 Uiso 1 1 calc R . . H2B H 0.5881 0.5008 0.6528 0.018 Uiso 1 1 calc R . . C3 C 0.65744(16) 0.3335(3) 0.8068(3) 0.0166(5) Uani 1 1 d . . . H3A H 0.7167 0.3853 0.8324 0.020 Uiso 1 1 calc R . . H3B H 0.6346 0.3486 0.8943 0.020 Uiso 1 1 calc R . . C4 C 0.66992(16) 0.1701(3) 0.7839(3) 0.0172(5) Uani 1 1 d . . . H4A H 0.6256 0.1121 0.8154 0.021 Uiso 1 1 calc R . . H4B H 0.7328 0.1389 0.8487 0.021 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 Se1 0.01053(15) 0.01023(16) 0.00988(15) 0.00018(12) 0.00440(11) -0.00009(12) Cl1 0.0156(3) 0.0138(3) 0.0172(3) 0.0029(2) 0.0054(2) 0.0019(2) S1 0.0127(3) 0.0111(3) 0.0151(3) -0.0005(2) 0.0058(2) -0.0001(2) C1 0.0194(11) 0.0103(11) 0.0141(11) 0.0002(9) 0.0086(9) -0.0016(9) C2 0.0147(11) 0.0141(12) 0.0177(11) -0.0036(9) 0.0063(9) 0.0013(9) C3 0.0163(11) 0.0192(13) 0.0137(11) -0.0044(10) 0.0047(9) -0.0027(9) C4 0.0200(12) 0.0176(12) 0.0100(11) 0.0010(9) 0.0003(9) -0.0032(10) _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 Se1 Cl1 2.4151(8) . ? Se1 Cl1 2.4151(7) 5_656 ? Se1 S1 2.5475(9) 5_656 ? Se1 S1 2.5475(9) . ? S1 C1 1.825(2) . ? S1 C4 1.836(2) . ? C1 C2 1.520(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.532(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.528(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? 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 Cl1 Se1 Cl1 180.0 . 5_656 ? Cl1 Se1 S1 82.63(3) . 5_656 ? Cl1 Se1 S1 97.37(3) 5_656 5_656 ? Cl1 Se1 S1 97.37(3) . . ? Cl1 Se1 S1 82.63(3) 5_656 . ? S1 Se1 S1 180.000(15) 5_656 . ? C1 S1 C4 94.21(11) . . ? C1 S1 Se1 106.35(8) . . ? C4 S1 Se1 98.44(8) . . ? C2 C1 S1 105.25(16) . . ? C2 C1 H1A 110.7 . . ? S1 C1 H1A 110.7 . . ? C2 C1 H1B 110.7 . . ? S1 C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? C1 C2 C3 106.14(19) . . ? C1 C2 H2A 110.5 . . ? C3 C2 H2A 110.5 . . ? C1 C2 H2B 110.5 . . ? C3 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? C4 C3 C2 107.55(19) . . ? C4 C3 H3A 110.2 . . ? C2 C3 H3A 110.2 . . ? C4 C3 H3B 110.2 . . ? C2 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? C3 C4 S1 106.77(16) . . ? C3 C4 H4A 110.4 . . ? S1 C4 H4A 110.4 . . ? C3 C4 H4B 110.4 . . ? S1 C4 H4B 110.4 . . ? H4A C4 H4B 108.6 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.380 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.090 loop_ _citation_id _citation_database_id_CSD primary CEQKUE data_12aj006rai _database_code_depnum_ccdc_archive 'CCDC 909375' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-09-15 _audit_author_name 'Webster, M.' _chemical_name_systematic ; trans-dibromobis(tetrahydrothiophene)selenium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H16 Br2 S2 Se' _chemical_formula_sum 'C8 H16 Br2 S2 Se' _chemical_formula_weight 415.11 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' 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.903(7) _cell_length_b 9.336(4) _cell_length_c 9.397(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.966(8) _cell_angle_gamma 90.00 _cell_volume 1284.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5390 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 9.428 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.433 # Expt'l Tmin & Tmax _exptl_absorpt_correction_T_max 1.000 # scaled to Tmax=1.0 _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, VHF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ Superbright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 ' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5715 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1451 _reflns_number_gt 1392 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+33.3311P] 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 1451 _refine_ls_number_parameters 61 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 Se1 Se 0.0000 1.0000 0.5000 0.01324(18) Uani 1 2 d S . . Br1 Br 0.10751(4) 0.80872(6) 0.67340(6) 0.01818(16) Uani 1 1 d . . . S1 S -0.14816(9) 0.85495(14) 0.40916(16) 0.0162(3) Uani 1 1 d . . . C1 C -0.1177(4) 0.6692(6) 0.4660(7) 0.0187(11) Uani 1 1 d . . . H1A H -0.0680 0.6640 0.5702 0.022 Uiso 1 1 calc R . . H1B H -0.1711 0.6153 0.4669 0.022 Uiso 1 1 calc R . . C2 C -0.0859(4) 0.6086(6) 0.3434(6) 0.0204(11) Uani 1 1 d . . . H2A H -0.0232 0.6413 0.3628 0.024 Uiso 1 1 calc R . . H2B H -0.0865 0.5025 0.3447 0.024 Uiso 1 1 calc R . . C3 C -0.1527(4) 0.6646(6) 0.1900(7) 0.0207(12) Uani 1 1 d . . . H3A H -0.2125 0.6163 0.1613 0.025 Uiso 1 1 calc R . . H3B H -0.1296 0.6459 0.1080 0.025 Uiso 1 1 calc R . . C4 C -0.1631(4) 0.8261(6) 0.2073(6) 0.0201(11) Uani 1 1 d . . . H4A H -0.2243 0.8588 0.1361 0.024 Uiso 1 1 calc R . . H4B H -0.1163 0.8795 0.1839 0.024 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 Se1 0.0124(3) 0.0136(4) 0.0130(4) 0.0004(3) 0.0042(3) 0.0000(3) Br1 0.0168(3) 0.0166(3) 0.0193(3) 0.0034(2) 0.0049(2) 0.0016(2) S1 0.0147(6) 0.0153(6) 0.0177(6) 0.0001(5) 0.0053(5) 0.0000(5) C1 0.021(3) 0.016(3) 0.018(3) 0.001(2) 0.006(2) -0.003(2) C2 0.019(3) 0.021(3) 0.019(3) -0.004(2) 0.006(2) 0.000(2) C3 0.017(3) 0.023(3) 0.018(3) -0.004(2) 0.002(2) -0.003(2) C4 0.020(3) 0.024(3) 0.012(2) -0.001(2) 0.002(2) -0.003(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 Se1 S1 2.5582(16) . ? Se1 S1 2.5582(16) 5_576 ? Se1 Br1 2.5677(8) . ? Se1 Br1 2.5677(8) 5_576 ? S1 C1 1.824(6) . ? S1 C4 1.837(6) . ? C1 C2 1.536(8) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.512(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.532(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? 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 S1 Se1 S1 180.0 . 5_576 ? S1 Se1 Br1 98.17(4) . . ? S1 Se1 Br1 81.83(4) 5_576 . ? S1 Se1 Br1 81.83(4) . 5_576 ? S1 Se1 Br1 98.17(4) 5_576 5_576 ? Br1 Se1 Br1 180.0 . 5_576 ? C1 S1 C4 94.3(3) . . ? C1 S1 Se1 107.50(19) . . ? C4 S1 Se1 98.84(19) . . ? C2 C1 S1 105.0(4) . . ? C2 C1 H1A 110.8 . . ? S1 C1 H1A 110.8 . . ? C2 C1 H1B 110.8 . . ? S1 C1 H1B 110.8 . . ? H1A C1 H1B 108.8 . . ? C3 C2 C1 105.8(5) . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2B 110.6 . . ? C1 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? C2 C3 C4 107.7(5) . . ? C2 C3 H3A 110.2 . . ? C4 C3 H3A 110.2 . . ? C2 C3 H3B 110.2 . . ? C4 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? C3 C4 S1 106.2(4) . . ? C3 C4 H4A 110.5 . . ? S1 C4 H4A 110.5 . . ? C3 C4 H4B 110.5 . . ? S1 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.868 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.178 data_12aj001k _database_code_depnum_ccdc_archive 'CCDC 909376' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-09-16 _audit_author_name 'Webster, M.' _chemical_name_systematic ; Dibromo[1,2-bis(methylsulfanyl)ethane-S,S']selenium(II) ; # MeSCH2CH2SMe = C4H10S2 # 2,5-dithiahexane # 1,2-bis(methylthio)ethane (iLab name (defaults)) # 1,2-bis(methylsulfanyl)ethane (iLab IUPAC name with selected options) # 1,2-bis(methylsulfanyl)ethane (chemspider) _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H10 Br2 S2 Se' _chemical_formula_sum 'C4 H10 Br2 S2 Se' _chemical_formula_weight 361.02 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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' 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 15.713(6) _cell_length_b 8.730(3) _cell_length_c 15.133(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.835(8) _cell_angle_gamma 90.00 _cell_volume 1952.7(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7403 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 12.384 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.657 # Expt'l Tmin & Tmax _exptl_absorpt_correction_T_max 1.000 # scaled to Tmax=1.0 _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, HF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ SuperBright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 ' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10204 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0790 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4458 _reflns_number_gt 3273 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+7.8315P] 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 4458 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Se1 Se 0.50769(5) 0.33956(7) 0.79700(4) 0.00995(15) Uani 1 1 d . . . Se2 Se 1.03193(4) 0.07452(8) 0.78461(4) 0.01046(15) Uani 1 1 d . . . Br1 Br 0.38077(5) 0.38311(8) 0.87453(4) 0.01404(16) Uani 1 1 d . . . Br2 Br 0.66192(5) 0.29020(8) 0.93822(4) 0.01561(16) Uani 1 1 d . . . Br3 Br 1.17171(5) 0.02791(8) 0.93899(4) 0.01577(16) Uani 1 1 d . . . Br4 Br 1.11544(5) 0.12120(8) 0.65972(4) 0.01567(16) Uani 1 1 d . . . S1 S 0.38341(11) 0.39569(19) 0.65253(10) 0.0122(4) Uani 1 1 d . . . S2 S 0.60043(11) 0.28201(19) 0.70200(10) 0.0118(3) Uani 1 1 d . . . S3 S 0.93800(12) 0.0405(2) 0.88061(10) 0.0128(4) Uani 1 1 d . . . S4 S 0.89538(12) 0.1331(2) 0.65235(10) 0.0129(4) Uani 1 1 d . . . C1 C 0.3228(5) 0.2210(8) 0.6214(5) 0.0219(17) Uani 1 1 d . . . H1A H 0.2817 0.2268 0.5562 0.033 Uiso 1 1 calc R . . H1B H 0.2876 0.2034 0.6630 0.033 Uiso 1 1 calc R . . H1C H 0.3655 0.1364 0.6279 0.033 Uiso 1 1 calc R . . C2 C 0.4437(5) 0.3978(8) 0.5688(4) 0.0132(14) Uani 1 1 d . . . H2A H 0.3997 0.3852 0.5045 0.016 Uiso 1 1 calc R . . H2B H 0.4735 0.4986 0.5718 0.016 Uiso 1 1 calc R . . C3 C 0.5146(5) 0.2725(8) 0.5874(4) 0.0160(15) Uani 1 1 d . . . H3A H 0.5441 0.2787 0.5392 0.019 Uiso 1 1 calc R . . H3B H 0.4840 0.1718 0.5804 0.019 Uiso 1 1 calc R . . C4 C 0.6568(5) 0.4581(8) 0.6932(5) 0.0154(15) Uani 1 1 d . . . H4A H 0.6802 0.4509 0.6411 0.023 Uiso 1 1 calc R . . H4B H 0.7070 0.4759 0.7519 0.023 Uiso 1 1 calc R . . H4C H 0.6137 0.5432 0.6819 0.023 Uiso 1 1 calc R . . C5 C 0.9433(5) 0.2258(7) 0.9353(4) 0.0170(16) Uani 1 1 d . . . H5A H 0.9335 0.3062 0.8877 0.026 Uiso 1 1 calc R . . H5B H 1.0028 0.2393 0.9836 0.026 Uiso 1 1 calc R . . H5C H 0.8963 0.2324 0.9642 0.026 Uiso 1 1 calc R . . C6 C 0.8258(5) 0.0458(8) 0.7916(4) 0.0161(15) Uani 1 1 d . . . H6A H 0.8113 -0.0568 0.7625 0.019 Uiso 1 1 calc R . . H6B H 0.7808 0.0695 0.8223 0.019 Uiso 1 1 calc R . . C7 C 0.8173(5) 0.1636(8) 0.7150(4) 0.0139(15) Uani 1 1 d . . . H7A H 0.8278 0.2669 0.7437 0.017 Uiso 1 1 calc R . . H7B H 0.7548 0.1610 0.6696 0.017 Uiso 1 1 calc R . . C8 C 0.8571(5) -0.0487(8) 0.5953(5) 0.0222(17) Uani 1 1 d . . . H8A H 0.8666 -0.1291 0.6429 0.033 Uiso 1 1 calc R . . H8B H 0.8914 -0.0735 0.5538 0.033 Uiso 1 1 calc R . . H8C H 0.7926 -0.0421 0.5582 0.033 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 Se1 0.0099(3) 0.0104(3) 0.0097(3) 0.0004(2) 0.0034(2) 0.0002(3) Se2 0.0079(3) 0.0107(3) 0.0122(3) -0.0002(3) 0.0026(2) -0.0002(3) Br1 0.0140(3) 0.0159(4) 0.0141(3) 0.0032(3) 0.0072(3) 0.0028(3) Br2 0.0138(3) 0.0168(4) 0.0133(3) -0.0002(3) 0.0007(3) -0.0012(3) Br3 0.0109(3) 0.0184(4) 0.0152(3) 0.0009(3) 0.0007(3) -0.0011(3) Br4 0.0120(3) 0.0193(4) 0.0173(3) 0.0027(3) 0.0071(3) 0.0000(3) S1 0.0091(8) 0.0136(9) 0.0138(7) 0.0022(7) 0.0037(6) 0.0020(7) S2 0.0101(8) 0.0129(9) 0.0118(7) -0.0008(7) 0.0029(6) 0.0013(7) S3 0.0122(8) 0.0153(9) 0.0107(7) 0.0003(7) 0.0037(6) -0.0007(7) S4 0.0113(8) 0.0140(9) 0.0140(7) 0.0024(7) 0.0051(6) 0.0025(7) C1 0.018(4) 0.023(4) 0.020(3) 0.010(3) 0.000(3) -0.005(3) C2 0.018(4) 0.013(4) 0.011(3) 0.003(3) 0.008(3) 0.003(3) C3 0.018(4) 0.016(4) 0.019(3) 0.006(3) 0.012(3) 0.003(3) C4 0.013(4) 0.012(4) 0.024(4) -0.003(3) 0.009(3) -0.003(3) C5 0.023(4) 0.008(4) 0.020(3) 0.000(3) 0.008(3) -0.003(3) C6 0.010(3) 0.019(4) 0.019(3) 0.004(3) 0.003(3) 0.007(3) C7 0.011(3) 0.016(4) 0.012(3) -0.004(3) 0.000(3) -0.004(3) C8 0.014(4) 0.024(4) 0.021(4) -0.002(3) -0.005(3) 0.010(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 Se1 S2 2.4217(19) . ? Se1 S1 2.4363(18) . ? Se1 Br1 2.6620(12) . ? Se1 Br2 2.6667(12) . ? Se2 S3 2.4150(19) . ? Se2 S4 2.4407(18) . ? Se2 Br3 2.6393(11) . ? Se2 Br4 2.6726(12) . ? S1 C1 1.775(7) . ? S1 C2 1.822(6) . ? S2 C4 1.801(7) . ? S2 C3 1.802(7) . ? S3 C5 1.806(7) . ? S3 C6 1.820(7) . ? S4 C7 1.807(7) . ? S4 C8 1.809(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.518(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.521(9) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 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 S2 Se1 S1 88.26(6) . . ? S2 Se1 Br1 169.42(5) . . ? S1 Se1 Br1 82.79(5) . . ? S2 Se1 Br2 82.87(5) . . ? S1 Se1 Br2 170.19(5) . . ? Br1 Se1 Br2 106.43(4) . . ? S3 Se2 S4 88.42(7) . . ? S3 Se2 Br3 86.76(5) . . ? S4 Se2 Br3 173.83(5) . . ? S3 Se2 Br4 172.34(5) . . ? S4 Se2 Br4 83.92(5) . . ? Br3 Se2 Br4 100.88(4) . . ? C1 S1 C2 100.6(3) . . ? C1 S1 Se1 105.1(2) . . ? C2 S1 Se1 100.3(2) . . ? C4 S2 C3 101.2(3) . . ? C4 S2 Se1 106.0(2) . . ? C3 S2 Se1 100.1(2) . . ? C5 S3 C6 101.4(3) . . ? C5 S3 Se2 102.9(2) . . ? C6 S3 Se2 100.9(2) . . ? C7 S4 C8 101.8(3) . . ? C7 S4 Se2 99.5(2) . . ? C8 S4 Se2 105.4(2) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 S1 112.7(4) . . ? C3 C2 H2A 109.1 . . ? S1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? S1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 S2 114.1(5) . . ? C2 C3 H3A 108.7 . . ? S2 C3 H3A 108.7 . . ? C2 C3 H3B 108.7 . . ? S2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? S2 C4 H4A 109.5 . . ? S2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? S2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? S3 C5 H5A 109.5 . . ? S3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? S3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 S3 113.1(5) . . ? C7 C6 H6A 109.0 . . ? S3 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? S3 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C6 C7 S4 113.7(5) . . ? C6 C7 H7A 108.8 . . ? S4 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? S4 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? S4 C8 H8A 109.5 . . ? S4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 S1 C2 C3 -67.5(6) . . . . ? Se1 S1 C2 C3 40.1(5) . . . . ? S1 C2 C3 S2 -59.3(6) . . . . ? C4 S2 C3 C2 -66.2(6) . . . . ? Se1 S2 C3 C2 42.5(5) . . . . ? C5 S3 C6 C7 66.8(6) . . . . ? Se2 S3 C6 C7 -38.9(5) . . . . ? S3 C6 C7 S4 59.1(6) . . . . ? C8 S4 C7 C6 64.8(5) . . . . ? Se2 S4 C7 C6 -43.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.057 _refine_diff_density_min -1.071 _refine_diff_density_rms 0.256 data_12aj002ra _database_code_depnum_ccdc_archive 'CCDC 909377' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-09-16 _audit_author_name 'Webster, M.' _chemical_name_systematic ; Dibromobis(4-bromo-1,2-bis(methylthio)benzene-S)selenium(II) ; # C8H9BrS2 # 4-bromo-1,2-bis(methylthio)benzene (I-Lab defaults) # 4-bromo-1,2-bis(methylsulfanyl)benzene (I-Lab selected options) _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Br4 S4 Se' _chemical_formula_sum 'C16 H18 Br4 S4 Se' _chemical_formula_weight 737.14 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' 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.963(7) _cell_length_b 11.782(6) _cell_length_c 12.718(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.534(8) _cell_angle_gamma 90.00 _cell_volume 2280.8(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5610 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 9.020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.659 # Expt'l Tmin & Tmax _exptl_absorpt_correction_T_max 1.000 # scaled to Tmax=1.0 _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, VHF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ Superbright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 ' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7467 _diffrn_reflns_av_R_equivalents 0.0822 _diffrn_reflns_av_sigmaI/netI 0.0974 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2599 _reflns_number_gt 1715 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.0379P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2599 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 Se1 Se 0.5000 0.28771(8) 0.2500 0.0150(2) Uani 1 2 d S . . Br1 Br 0.50275(4) 0.42620(6) 0.11064(6) 0.02163(19) Uani 1 1 d . . . Br2 Br 0.35285(5) 0.30171(7) -0.31262(6) 0.0302(2) Uani 1 1 d . . . S1 S 0.50700(10) 0.11249(14) 0.10606(14) 0.0180(4) Uani 1 1 d . . . S2 S 0.32991(11) 0.04592(15) 0.12575(14) 0.0204(4) Uani 1 1 d . . . C1 C 0.4130(4) 0.1462(5) -0.0081(5) 0.0183(14) Uani 1 1 d . . . C2 C 0.3314(4) 0.1130(5) 0.0035(5) 0.0190(15) Uani 1 1 d . . . C3 C 0.2559(4) 0.1393(5) -0.0840(5) 0.0200(15) Uani 1 1 d . . . H3 H 0.1996 0.1200 -0.0786 0.024 Uiso 1 1 calc R . . C4 C 0.2625(4) 0.1929(5) -0.1778(6) 0.0197(15) Uani 1 1 d . . . H4 H 0.2110 0.2094 -0.2368 0.024 Uiso 1 1 calc R . . C5 C 0.3444(4) 0.2225(5) -0.1855(5) 0.0195(14) Uani 1 1 d . . . C6 C 0.4205(4) 0.2012(5) -0.1011(6) 0.0198(15) Uani 1 1 d . . . H6 H 0.4762 0.2235 -0.1067 0.024 Uiso 1 1 calc R . . C7 C 0.5985(4) 0.1539(6) 0.0615(5) 0.0224(15) Uani 1 1 d . . . H7A H 0.5950 0.1160 -0.0083 0.034 Uiso 1 1 calc R . . H7B H 0.6532 0.1322 0.1174 0.034 Uiso 1 1 calc R . . H7C H 0.5975 0.2363 0.0509 0.034 Uiso 1 1 calc R . . C8 C 0.2164(4) 0.0066(6) 0.0971(6) 0.0296(18) Uani 1 1 d . . . H8A H 0.1796 0.0749 0.0805 0.044 Uiso 1 1 calc R . . H8B H 0.2079 -0.0316 0.1616 0.044 Uiso 1 1 calc R . . H8C H 0.1997 -0.0448 0.0336 0.044 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 Se1 0.0145(4) 0.0197(5) 0.0117(5) 0.000 0.0054(3) 0.000 Br1 0.0254(4) 0.0232(4) 0.0180(4) 0.0044(3) 0.0092(3) -0.0020(3) Br2 0.0313(4) 0.0398(5) 0.0217(4) 0.0090(3) 0.0111(3) 0.0055(3) S1 0.0179(8) 0.0221(8) 0.0146(8) -0.0020(7) 0.0056(6) 0.0006(7) S2 0.0197(8) 0.0259(9) 0.0168(9) 0.0013(7) 0.0074(7) 0.0001(7) C1 0.017(3) 0.019(3) 0.019(4) -0.004(3) 0.004(3) 0.000(3) C2 0.026(4) 0.014(3) 0.016(3) -0.004(3) 0.005(3) -0.001(3) C3 0.017(3) 0.023(4) 0.019(4) -0.007(3) 0.004(3) 0.001(3) C4 0.019(3) 0.021(3) 0.019(4) -0.006(3) 0.005(3) -0.001(3) C5 0.026(3) 0.022(3) 0.010(3) 0.000(3) 0.005(3) 0.002(3) C6 0.014(3) 0.020(4) 0.027(4) -0.001(3) 0.009(3) 0.003(3) C7 0.019(3) 0.030(4) 0.017(4) -0.003(3) 0.004(3) -0.002(3) C8 0.026(4) 0.032(4) 0.031(5) 0.004(3) 0.007(3) -0.002(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 Se1 Br1 2.4192(12) 2_655 ? Se1 Br1 2.4192(12) . ? Se1 S1 2.784(2) . ? Se1 S1 2.784(2) 2_655 ? Br2 C5 1.906(7) . ? S1 C7 1.786(7) . ? S1 C1 1.791(6) . ? S2 C2 1.751(7) . ? S2 C8 1.798(7) . ? C1 C6 1.385(9) . ? C1 C2 1.410(9) . ? C2 C3 1.407(8) . ? C3 C4 1.381(9) . ? C3 H3 0.9500 . ? C4 C5 1.386(9) . ? C4 H4 0.9500 . ? C5 C6 1.380(8) . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 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 Br1 Se1 Br1 95.18(6) 2_655 . ? Br1 Se1 S1 174.38(5) 2_655 . ? Br1 Se1 S1 90.30(5) . . ? Br1 Se1 S1 90.30(5) 2_655 2_655 ? Br1 Se1 S1 174.38(5) . 2_655 ? S1 Se1 S1 84.26(8) . 2_655 ? C7 S1 C1 104.3(3) . . ? C7 S1 Se1 101.8(2) . . ? C1 S1 Se1 100.3(2) . . ? C2 S2 C8 102.6(3) . . ? C6 C1 C2 122.7(6) . . ? C6 C1 S1 121.9(5) . . ? C2 C1 S1 115.3(5) . . ? C3 C2 C1 117.0(6) . . ? C3 C2 S2 124.4(5) . . ? C1 C2 S2 118.6(5) . . ? C4 C3 C2 121.0(6) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.6(6) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 121.9(6) . . ? C6 C5 Br2 118.6(5) . . ? C4 C5 Br2 119.5(5) . . ? C5 C6 C1 117.8(6) . . ? C5 C6 H6 121.1 . . ? C1 C6 H6 121.1 . . ? S1 C7 H7A 109.5 . . ? S1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? S2 C8 H8A 109.5 . . ? S2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.847 _refine_diff_density_min -1.235 _refine_diff_density_rms 0.200 data_12aj001ra _database_code_depnum_ccdc_archive 'CCDC 909378' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-09-18 _audit_author_name 'Webster, M.' _chemical_name_systematic ; catena-dibromo(2,6-dithiaheptane-S,S')selenium(II) ; # MeS(CH2)3SMe = C5H12S2 # 2,6-dithiaheptane # 1,3-Bis(methylsulfanyl)propane (Chemspider IUPAC) # 1,3-Bis(methylthio)propane (Chemspider) _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H12 Br2 S2 Se' _chemical_formula_sum 'C5 H12 Br2 S2 Se' _chemical_formula_weight 375.05 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' 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.0866(16) _cell_length_b 8.0491(11) _cell_length_c 14.533(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.211(8) _cell_angle_gamma 90.00 _cell_volume 1114.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2485 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 10.856 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.659 # Expt'l Tmin & Tmax _exptl_absorpt_correction_T_max 1.000 # scaled to Tmax=1.0 _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, VHF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ Superbright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 ' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2684 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1269 _reflns_number_gt 1198 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+319.8433P] 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 1269 _refine_ls_number_parameters 49 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1088 _refine_ls_R_factor_gt 0.1052 _refine_ls_wR_factor_ref 0.2814 _refine_ls_wR_factor_gt 0.2801 _refine_ls_goodness_of_fit_ref 1.271 _refine_ls_restrained_S_all 1.271 _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 Se1 Se 0.7500 0.2500 0.5000 0.0129(6) Uani 1 2 d S . . Br1 Br 0.7274(2) -0.0172(2) 0.40001(14) 0.0173(5) Uani 1 1 d . . . S1 S 0.7954(5) 0.0905(6) 0.6566(3) 0.0155(9) Uani 1 1 d . . . C1 C 0.655(2) -0.055(3) 0.6324(14) 0.021(4) Uani 1 1 d . . . H1A H 0.6534 -0.1251 0.5768 0.032 Uiso 1 1 calc R . . H1B H 0.5655 0.0044 0.6173 0.032 Uiso 1 1 calc R . . H1C H 0.6682 -0.1256 0.6899 0.032 Uiso 1 1 calc R . . C2 C 0.942(2) -0.039(3) 0.6570(13) 0.019(4) Uani 1 1 d . . . H2A H 0.9122 -0.1153 0.6002 0.023 Uiso 1 1 calc R . . H2B H 1.0183 0.0318 0.6498 0.023 Uiso 1 1 calc R . . C3 C 1.0000 -0.142(4) 0.7500 0.024(6) Uani 1 2 d S . . H3A H 0.9242 -0.2150 0.7562 0.029 Uiso 0.50 1 calc PR . . H3B H 1.0758 -0.2150 0.7438 0.029 Uiso 0.50 1 calc PR . . 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 Se1 0.0147(12) 0.0142(12) 0.0080(11) -0.0029(9) 0.0012(9) 0.0018(9) Br1 0.0217(10) 0.0153(9) 0.0146(9) -0.0055(7) 0.0054(7) -0.0020(7) S1 0.018(2) 0.015(2) 0.012(2) 0.0012(16) 0.0031(16) 0.0015(17) C1 0.020(9) 0.028(11) 0.017(9) 0.007(8) 0.009(7) -0.009(8) C2 0.015(9) 0.028(11) 0.011(8) 0.002(8) 0.002(7) 0.006(8) C3 0.012(12) 0.024(15) 0.034(16) 0.000 0.005(11) 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 Se1 S1 2.520(5) . ? Se1 S1 2.520(5) 7_656 ? Se1 Br1 2.5636(19) . ? Se1 Br1 2.5636(19) 7_656 ? S1 C1 1.79(2) . ? S1 C2 1.81(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.53(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C2 1.53(3) 2_756 ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? 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 S1 Se1 S1 180.000(1) . 7_656 ? S1 Se1 Br1 92.30(12) . . ? S1 Se1 Br1 87.70(12) 7_656 . ? S1 Se1 Br1 87.70(12) . 7_656 ? S1 Se1 Br1 92.30(12) 7_656 7_656 ? Br1 Se1 Br1 180.0 . 7_656 ? C1 S1 C2 102.5(10) . . ? C1 S1 Se1 105.1(7) . . ? C2 S1 Se1 101.7(6) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 S1 112.9(12) . . ? C3 C2 H2A 109.0 . . ? S1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? S1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C2 114(3) 2_756 . ? C2 C3 H3A 108.7 2_756 . ? C2 C3 H3A 108.7 . . ? C2 C3 H3B 108.7 2_756 . ? C2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? 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 # S1 Se1 S1 C1 78(100) 7_656 . . . ? # S1 Se1 S1 C2 -175(100) 7_656 . . . ? Br1 Se1 S1 C1 -52.3(8) . . . . ? Br1 Se1 S1 C1 127.7(8) 7_656 . . . ? Br1 Se1 S1 C2 54.3(7) . . . . ? Br1 Se1 S1 C2 -125.7(7) 7_656 . . . ? C1 S1 C2 C3 -75.8(17) . . . . ? Se1 S1 C2 C3 175.6(14) . . . . ? S1 C2 C3 C2 -61.8(10) . . . 2_756 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 4.565 _refine_diff_density_min -3.077 _refine_diff_density_rms 0.532 data_12aj012r _database_code_depnum_ccdc_archive 'CCDC 909379' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-10-27 _audit_author_name 'Webster, M.' _chemical_name_systematic ; bis[3,4-bis(methylsulfanyl)phenyl](methyl)[2-(methylsulfanyl)phenyl]sulfonium hexachloroselenate(IV) dichloroselenium(II) ; # [C16H19S4]+ # [3,4-bis(methylthio)phenyl](methyl)[2-(methylthio)phenyl]sulfonium # (I-Lab defaults) # [3,4-bis(methylsulfanyl)phenyl](methyl)[2-(methylsulfanyl)phenyl]sulfonium # (I-Lab selected options) _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C16 H19 S4 1+), Cl6 Se 2-, 1.76(Cl2 Se)' _chemical_formula_sum 'C32 H38 Cl9.52 S8 Se2.76' _chemical_formula_weight 1234.52 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' Cl Cl 0.1484 0.1585 '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' _space_group_IT_number 2 _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.095(4) _cell_length_b 10.111(4) _cell_length_c 12.633(5) _cell_angle_alpha 112.040(8) _cell_angle_beta 96.489(7) _cell_angle_gamma 92.494(7) _cell_volume 1182.5(8) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8152 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.734 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 613.7 # # NB Current version of checkcif gives wrong value for F(000) (614.7) # _exptl_absorpt_coefficient_mu 3.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.499 # Expt'l Tmin & Tmax _exptl_absorpt_correction_T_max 1.000 # scaled to Tmax=1.0 _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, VHF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ Superbright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 ' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10466 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0793 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5314 _reflns_number_gt 3902 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.0183P)^2^+3.7721P] 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 5314 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.81068(11) 0.53998(12) 0.27377(10) 0.0163(2) Uani 1 1 d . . . S2 S 0.6846(2) 0.5133(2) 0.03865(14) 0.0607(6) Uani 1 1 d . . . S3 S 0.32102(12) 0.59074(13) 0.42534(11) 0.0217(3) Uani 1 1 d . . . S4 S 0.26552(12) 0.26727(13) 0.33542(11) 0.0213(3) Uani 1 1 d . . . C1 C 0.9130(5) 0.5302(5) 0.3958(4) 0.0212(10) Uani 1 1 d . . . H1A H 0.9014 0.4328 0.3945 0.032 Uiso 1 1 calc R . . H1B H 0.8862 0.5981 0.4670 0.032 Uiso 1 1 calc R . . H1C H 1.0071 0.5544 0.3927 0.032 Uiso 1 1 calc R . . C2 C 0.8704(5) 0.4107(5) 0.1532(4) 0.0196(10) Uani 1 1 d . . . C3 C 0.8161(5) 0.4066(6) 0.0439(4) 0.0282(12) Uani 1 1 d . . . C4 C 0.8659(6) 0.3131(7) -0.0521(5) 0.0375(14) Uani 1 1 d . . . H4 H 0.8312 0.3073 -0.1270 0.045 Uiso 1 1 calc R . . C5 C 0.9652(6) 0.2290(6) -0.0393(5) 0.0392(15) Uani 1 1 d . . . H5 H 1.0001 0.1677 -0.1054 0.047 Uiso 1 1 calc R . . C6 C 1.0146(6) 0.2325(7) 0.0681(5) 0.0392(14) Uani 1 1 d . . . H6 H 1.0816 0.1722 0.0754 0.047 Uiso 1 1 calc R . . C7 C 0.9674(5) 0.3227(6) 0.1642(4) 0.0269(11) Uani 1 1 d . . . H7 H 1.0011 0.3248 0.2382 0.032 Uiso 1 1 calc R . . C8 C 0.6824(7) 0.5310(8) -0.0962(6) 0.0533(18) Uani 1 1 d . . . H8A H 0.7724 0.5643 -0.1032 0.080 Uiso 1 1 calc R . . H8B H 0.6198 0.6006 -0.1009 0.080 Uiso 1 1 calc R . . H8C H 0.6538 0.4379 -0.1587 0.080 Uiso 1 1 calc R . . C9 C 0.6552(4) 0.4556(5) 0.2825(4) 0.0173(9) Uani 1 1 d . . . C10 C 0.5638(4) 0.5465(5) 0.3398(4) 0.0159(9) Uani 1 1 d . . . H10 H 0.5827 0.6475 0.3671 0.019 Uiso 1 1 calc R . . C11 C 0.4446(4) 0.4878(5) 0.3565(4) 0.0166(9) Uani 1 1 d . . . C12 C 0.4181(5) 0.3352(5) 0.3107(4) 0.0180(10) Uani 1 1 d . . . C13 C 0.5096(5) 0.2488(5) 0.2515(4) 0.0227(10) Uani 1 1 d . . . H13 H 0.4898 0.1477 0.2197 0.027 Uiso 1 1 calc R . . C14 C 0.6294(5) 0.3074(5) 0.2380(4) 0.0215(10) Uani 1 1 d . . . H14 H 0.6930 0.2477 0.1989 0.026 Uiso 1 1 calc R . . C15 C 0.3926(5) 0.7719(5) 0.4671(4) 0.0233(11) Uani 1 1 d . . . H15A H 0.4761 0.7877 0.5198 0.035 Uiso 1 1 calc R . . H15B H 0.3294 0.8384 0.5059 0.035 Uiso 1 1 calc R . . H15C H 0.4114 0.7884 0.3984 0.035 Uiso 1 1 calc R . . C16 C 0.2688(5) 0.0769(5) 0.2651(4) 0.0271(12) Uani 1 1 d . . . H16A H 0.2737 0.0520 0.1830 0.041 Uiso 1 1 calc R . . H16B H 0.1872 0.0282 0.2740 0.041 Uiso 1 1 calc R . . H16C H 0.3472 0.0465 0.3001 0.041 Uiso 1 1 calc R . . Se1 Se 0.0000 0.0000 0.5000 0.01462(15) Uani 1 2 d S . . Cl1 Cl 0.22863(11) 0.10631(12) 0.54751(10) 0.0214(3) Uani 1 1 d . . . Cl2 Cl 0.05058(12) -0.13186(12) 0.62240(10) 0.0231(3) Uani 1 1 d . . . Cl3 Cl -0.06218(11) 0.19194(12) 0.66028(10) 0.0199(2) Uani 1 1 d . . . Se2 Se 0.29029(6) 0.07076(6) 0.77369(5) 0.02282(15) Uani 0.80 1 d P . . Cl4 Cl 0.2904(2) 0.03603(18) 0.93623(15) 0.0457(4) Uani 0.80 1 d P . . Cl5 Cl 0.48299(18) 0.19255(18) 0.81688(18) 0.0477(5) Uani 0.80 1 d P . . Se3 Se 0.4706(7) 0.2124(7) 0.9850(6) 0.0289(15) Uani 0.08 1 d P . . Cl6 Cl 0.2904(2) 0.03603(18) 0.93623(15) 0.0457(4) Uani 0.08 1 d P . . Cl7 Cl 0.48299(18) 0.19255(18) 0.81688(18) 0.0477(5) Uani 0.08 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0143(5) 0.0186(6) 0.0167(6) 0.0076(5) 0.0017(5) 0.0009(4) S2 0.0768(13) 0.0831(14) 0.0258(8) 0.0217(9) 0.0019(9) 0.0520(11) S3 0.0166(6) 0.0219(6) 0.0271(7) 0.0089(5) 0.0061(5) 0.0059(5) S4 0.0164(6) 0.0206(6) 0.0274(6) 0.0093(5) 0.0052(5) 0.0001(5) C1 0.021(2) 0.027(3) 0.015(2) 0.009(2) -0.001(2) -0.002(2) C2 0.015(2) 0.024(2) 0.020(2) 0.008(2) 0.0031(19) -0.0005(19) C3 0.027(3) 0.042(3) 0.017(2) 0.012(2) 0.006(2) 0.005(2) C4 0.030(3) 0.056(4) 0.020(3) 0.009(3) 0.002(2) 0.001(3) C5 0.031(3) 0.046(4) 0.028(3) -0.003(3) 0.016(3) 0.006(3) C6 0.032(3) 0.047(4) 0.037(3) 0.010(3) 0.016(3) 0.019(3) C7 0.020(3) 0.040(3) 0.022(3) 0.012(2) 0.005(2) 0.007(2) C8 0.055(4) 0.064(5) 0.049(4) 0.037(4) -0.010(3) -0.001(4) C9 0.013(2) 0.021(2) 0.019(2) 0.009(2) -0.0003(19) -0.0008(18) C10 0.018(2) 0.018(2) 0.014(2) 0.0087(18) -0.0011(18) 0.0046(18) C11 0.017(2) 0.021(2) 0.013(2) 0.0089(19) 0.0001(18) 0.0051(18) C12 0.017(2) 0.022(2) 0.017(2) 0.010(2) 0.0019(19) 0.0000(19) C13 0.022(3) 0.020(2) 0.025(3) 0.006(2) 0.006(2) 0.003(2) C14 0.016(2) 0.026(3) 0.025(3) 0.010(2) 0.008(2) 0.007(2) C15 0.022(3) 0.015(2) 0.029(3) 0.003(2) 0.004(2) 0.005(2) C16 0.020(3) 0.029(3) 0.028(3) 0.005(2) 0.009(2) -0.003(2) Se1 0.0144(3) 0.0134(3) 0.0167(3) 0.0062(3) 0.0030(3) 0.0016(2) Cl1 0.0192(6) 0.0191(5) 0.0266(6) 0.0089(5) 0.0061(5) 0.0009(4) Cl2 0.0226(6) 0.0208(6) 0.0278(6) 0.0118(5) 0.0022(5) 0.0021(5) Cl3 0.0206(6) 0.0182(5) 0.0200(6) 0.0051(4) 0.0063(5) 0.0025(4) Se2 0.0196(3) 0.0215(3) 0.0277(3) 0.0088(3) 0.0055(3) 0.0059(2) Cl4 0.0643(12) 0.0388(9) 0.0396(9) 0.0142(8) 0.0249(9) 0.0248(9) Cl5 0.0333(9) 0.0361(9) 0.0665(12) 0.0114(9) 0.0081(9) 0.0027(7) Se3 0.034(4) 0.031(4) 0.022(3) 0.011(3) -0.004(3) 0.008(3) Cl6 0.0643(12) 0.0388(9) 0.0396(9) 0.0142(8) 0.0249(9) 0.0248(9) Cl7 0.0333(9) 0.0361(9) 0.0665(12) 0.0114(9) 0.0081(9) 0.0027(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.782(5) . ? S1 C9 1.788(4) . ? S1 C1 1.793(5) . ? S2 C3 1.758(6) . ? S2 C8 1.776(6) . ? S3 C11 1.754(5) . ? S3 C15 1.797(5) . ? S4 C12 1.766(5) . ? S4 C16 1.796(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C7 1.382(7) . ? C2 C3 1.411(7) . ? C3 C4 1.391(7) . ? C4 C5 1.376(8) . ? C4 H4 0.9500 . ? C5 C6 1.379(8) . ? C5 H5 0.9500 . ? C6 C7 1.367(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.389(6) . ? C9 C10 1.395(6) . ? C10 C11 1.390(6) . ? C10 H10 0.9500 . ? C11 C12 1.431(6) . ? C12 C13 1.383(6) . ? C13 C14 1.380(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? Se1 Cl3 2.3884(13) 2_556 ? Se1 Cl3 2.3884(13) . ? Se1 Cl1 2.4145(14) 2_556 ? Se1 Cl1 2.4145(14) . ? Se1 Cl2 2.4203(13) 2_556 ? Se1 Cl2 2.4203(13) . ? Cl1 Se2 3.0117(17) . ? Cl2 Se2 3.0481(16) . ? Se2 Cl5 2.1554(19) . ? Se2 Cl4 2.209(2) . ? Cl4 Se3 2.347(7) . ? Cl5 Se3 2.075(7) . ? 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 S1 C9 104.1(2) . . ? C2 S1 C1 103.8(2) . . ? C9 S1 C1 100.4(2) . . ? C3 S2 C8 104.6(3) . . ? C11 S3 C15 103.4(2) . . ? C12 S4 C16 102.9(2) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 C3 121.2(5) . . ? C7 C2 S1 122.9(4) . . ? C3 C2 S1 115.9(4) . . ? C4 C3 C2 117.7(5) . . ? C4 C3 S2 124.8(4) . . ? C2 C3 S2 117.5(4) . . ? C5 C4 C3 120.4(5) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.9(5) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 120.1(5) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 119.7(5) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? S2 C8 H8A 109.5 . . ? S2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 122.1(4) . . ? C14 C9 S1 121.5(4) . . ? C10 C9 S1 116.3(3) . . ? C11 C10 C9 119.3(4) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 118.5(4) . . ? C10 C11 S3 123.6(4) . . ? C12 C11 S3 117.8(3) . . ? C13 C12 C11 120.4(4) . . ? C13 C12 S4 123.3(4) . . ? C11 C12 S4 116.3(4) . . ? C14 C13 C12 120.9(4) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C9 118.7(4) . . ? C13 C14 H14 120.6 . . ? C9 C14 H14 120.6 . . ? S3 C15 H15A 109.5 . . ? S3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S4 C16 H16A 109.5 . . ? S4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Cl3 Se1 Cl3 180.00(5) 2_556 . ? Cl3 Se1 Cl1 90.52(4) 2_556 2_556 ? Cl3 Se1 Cl1 89.48(4) . 2_556 ? Cl3 Se1 Cl1 89.48(4) 2_556 . ? Cl3 Se1 Cl1 90.52(4) . . ? Cl1 Se1 Cl1 180.0 2_556 . ? Cl3 Se1 Cl2 89.77(5) 2_556 2_556 ? Cl3 Se1 Cl2 90.23(5) . 2_556 ? Cl1 Se1 Cl2 89.79(4) 2_556 2_556 ? Cl1 Se1 Cl2 90.21(4) . 2_556 ? Cl3 Se1 Cl2 90.23(5) 2_556 . ? Cl3 Se1 Cl2 89.77(5) . . ? Cl1 Se1 Cl2 90.21(4) 2_556 . ? Cl1 Se1 Cl2 89.79(4) . . ? Cl2 Se1 Cl2 180.0 2_556 . ? Se1 Cl1 Se2 97.21(4) . . ? Se1 Cl2 Se2 96.14(4) . . ? Cl5 Se2 Cl4 97.34(8) . . ? Cl5 Se2 Cl1 93.63(6) . . ? Cl4 Se2 Cl1 168.20(6) . . ? Cl5 Se2 Cl2 158.15(6) . . ? Cl4 Se2 Cl2 101.62(6) . . ? Cl1 Se2 Cl2 68.54(4) . . ? Se2 Cl4 Se3 78.35(17) . . ? Se3 Cl5 Se2 85.8(2) . . ? Cl5 Se3 Cl4 95.4(3) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.313 _refine_diff_density_min -0.816 _refine_diff_density_rms 0.134 data_12aj013r _database_code_depnum_ccdc_archive 'CCDC 909380' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-10-22 _audit_author_name 'Webster, M.' _chemical_name_systematic ; bis[2-methyl-1-(methylthio)-1,3-dihydro-2-benzothiophenium] hexachlorodiselenate(II) ; # [C10H13S2]+ # 2-methyl-1-(methylthio)-1,3-dihydro-2-benzothiophenium (I-Lab defaults) # 2-methyl-1-(methylsulfanyl)-1,3-dihydro-2-benzothiophenium # (I-Lab selected options) _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C10 H13 S2 1+), Cl6 Se2 2-' _chemical_formula_sum 'C20 H26 Cl6 S4 Se2' _chemical_formula_weight 765.27 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' Cl Cl 0.1484 0.1585 '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' _space_group_IT_number 2 _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.607(4) _cell_length_b 9.262(5) _cell_length_c 10.897(6) _cell_angle_alpha 93.373(7) _cell_angle_beta 96.211(7) _cell_angle_gamma 107.647(8) _cell_volume 724.0(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5239 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description chip _exptl_crystal_colour yellow _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.755 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 3.407 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.655 # Expt'l Tmin & Tmax _exptl_absorpt_correction_T_max 1.000 # scaled to Tmax=1.0 _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, VHF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ Superbright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 ' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6696 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_sigmaI/netI 0.1085 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3282 _reflns_number_gt 2246 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.0305P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3282 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 S1 S 0.29126(16) 0.18241(15) 0.34845(12) 0.0237(3) Uani 1 1 d . . . S2 S 0.49983(17) 0.27538(16) 0.13534(13) 0.0273(3) Uani 1 1 d . . . C1 C 0.1924(7) 0.2837(6) 0.4530(5) 0.0288(13) Uani 1 1 d . . . H1A H 0.0815 0.2999 0.4091 0.043 Uiso 1 1 calc R . . H1B H 0.2840 0.3823 0.4839 0.043 Uiso 1 1 calc R . . H1C H 0.1576 0.2240 0.5229 0.043 Uiso 1 1 calc R . . C2 C 0.0855(6) 0.0414(5) 0.2681(5) 0.0224(11) Uani 1 1 d . . . H2A H 0.1165 -0.0485 0.2351 0.027 Uiso 1 1 calc R . . H2B H -0.0088 0.0079 0.3251 0.027 Uiso 1 1 calc R . . C3 C 0.0122(7) 0.1155(6) 0.1639(5) 0.0213(11) Uani 1 1 d . . . C4 C -0.1595(6) 0.0558(6) 0.0936(5) 0.0232(12) Uani 1 1 d . . . H4 H -0.2443 -0.0370 0.1113 0.028 Uiso 1 1 calc R . . C5 C -0.2071(7) 0.1330(6) -0.0035(5) 0.0263(12) Uani 1 1 d . . . H5 H -0.3250 0.0923 -0.0529 0.032 Uiso 1 1 calc R . . C6 C -0.0840(7) 0.2693(6) -0.0292(5) 0.0280(13) Uani 1 1 d . . . H6 H -0.1191 0.3217 -0.0953 0.034 Uiso 1 1 calc R . . C7 C 0.0899(7) 0.3297(6) 0.0408(5) 0.0246(12) Uani 1 1 d . . . H7 H 0.1758 0.4214 0.0222 0.030 Uiso 1 1 calc R . . C8 C 0.1349(6) 0.2519(6) 0.1391(5) 0.0236(12) Uani 1 1 d . . . C9 C 0.3206(6) 0.3030(6) 0.2202(5) 0.0221(11) Uani 1 1 d . . . H9 H 0.3522 0.4124 0.2524 0.027 Uiso 1 1 calc R . . C10 C 0.7019(6) 0.3681(6) 0.2480(5) 0.0279(13) Uani 1 1 d . . . H10A H 0.7046 0.4726 0.2713 0.042 Uiso 1 1 calc R . . H10B H 0.8150 0.3699 0.2118 0.042 Uiso 1 1 calc R . . H10C H 0.6956 0.3121 0.3217 0.042 Uiso 1 1 calc R . . Se1 Se 0.40138(6) 0.81344(6) 0.38010(5) 0.02148(16) Uani 1 1 d . . . Cl1 Cl 0.27931(15) 0.95307(14) 0.56275(13) 0.0263(3) Uani 1 1 d . . . Cl2 Cl 0.12590(17) 0.62529(15) 0.35225(13) 0.0302(3) Uani 1 1 d . . . Cl3 Cl 0.52110(17) 0.71210(15) 0.22770(13) 0.0289(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0192(6) 0.0303(8) 0.0235(8) 0.0042(6) 0.0009(5) 0.0106(6) S2 0.0188(6) 0.0336(8) 0.0284(8) 0.0004(6) 0.0026(6) 0.0072(6) C1 0.026(3) 0.026(3) 0.037(4) 0.001(3) 0.005(2) 0.012(2) C2 0.022(2) 0.019(3) 0.026(3) 0.003(2) 0.004(2) 0.007(2) C3 0.023(3) 0.025(3) 0.019(3) 0.000(2) 0.002(2) 0.014(2) C4 0.018(2) 0.028(3) 0.026(3) 0.000(2) 0.004(2) 0.009(2) C5 0.020(3) 0.038(3) 0.023(3) -0.005(3) -0.003(2) 0.015(2) C6 0.033(3) 0.034(3) 0.023(3) 0.002(3) -0.004(2) 0.021(3) C7 0.025(3) 0.026(3) 0.024(3) 0.002(2) 0.003(2) 0.011(2) C8 0.021(3) 0.027(3) 0.024(3) 0.001(2) -0.001(2) 0.010(2) C9 0.020(2) 0.020(3) 0.027(3) 0.001(2) 0.002(2) 0.009(2) C10 0.016(2) 0.031(3) 0.036(4) -0.004(3) 0.003(2) 0.008(2) Se1 0.0174(3) 0.0222(3) 0.0251(3) 0.0037(2) -0.0014(2) 0.0079(2) Cl1 0.0178(6) 0.0286(8) 0.0327(8) 0.0034(6) 0.0048(5) 0.0069(5) Cl2 0.0217(6) 0.0267(8) 0.0374(9) 0.0007(6) -0.0009(6) 0.0024(5) Cl3 0.0296(7) 0.0273(8) 0.0310(8) -0.0007(6) 0.0061(6) 0.0108(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.797(5) . ? S1 C2 1.803(5) . ? S1 C9 1.830(5) . ? S2 C9 1.799(5) . ? S2 C10 1.810(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.502(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.377(6) . ? C3 C8 1.386(7) . ? C4 C5 1.387(6) . ? C4 H4 0.9500 . ? C5 C6 1.390(7) . ? C5 H5 0.9500 . ? C6 C7 1.388(7) . ? C6 H6 0.9500 . ? C7 C8 1.395(6) . ? C7 H7 0.9500 . ? C8 C9 1.509(6) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? Se1 Cl2 2.2598(16) . ? Se1 Cl3 2.2651(16) . ? Se1 Cl1 2.7057(17) . ? 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 S1 C2 101.4(2) . . ? C1 S1 C9 101.6(2) . . ? C2 S1 C9 94.0(2) . . ? C9 S2 C10 99.6(2) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 S1 106.7(3) . . ? C3 C2 H2A 110.4 . . ? S1 C2 H2A 110.4 . . ? C3 C2 H2B 110.4 . . ? S1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? C4 C3 C8 120.4(4) . . ? C4 C3 C2 125.0(5) . . ? C8 C3 C2 114.6(4) . . ? C3 C4 C5 119.2(5) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 120.6(5) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 120.6(5) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 118.1(5) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? C3 C8 C7 121.1(5) . . ? C3 C8 C9 115.4(4) . . ? C7 C8 C9 123.5(5) . . ? C8 C9 S2 110.5(4) . . ? C8 C9 S1 105.3(3) . . ? S2 C9 S1 110.2(2) . . ? C8 C9 H9 110.3 . . ? S2 C9 H9 110.3 . . ? S1 C9 H9 110.3 . . ? S2 C10 H10A 109.5 . . ? S2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? S2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Cl2 Se1 Cl3 94.68(6) . . ? Cl2 Se1 Cl1 89.37(6) . . ? Cl3 Se1 Cl1 175.87(5) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 Cl1 3.238(2) . 1_545 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.896 _refine_diff_density_min -0.720 _refine_diff_density_rms 0.155 data_12aj007ra _database_code_depnum_ccdc_archive 'CCDC 909381' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-10-23 _audit_author_name 'Webster, M.' _chemical_name_systematic ; bis(2-methyl-1,3-dihydro-2-benzothiophenium) tetrabromoselenate(II) ; # [C9H11S]^+^ # 2-methyl-1,3-dihydro-2-benzothiophenium (I-Lab defaults) # 2-methyl-1,3-dihydro-2-benzothiophenium (I-Lab selected options) _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C9 H11 S 1+), Br4 Se 2-' _chemical_formula_sum 'C18 H22 Br4 S2 Se' _chemical_formula_weight 701.08 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' S S 0.1246 0.1234 '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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.882(4) _cell_length_b 10.349(3) _cell_length_c 15.570(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.937(8) _cell_angle_gamma 90.00 _cell_volume 2268.2(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8615 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description chip _exptl_crystal_colour yellow _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.053 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 8.887 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.757 # _exptl_absorpt_correction_T_max 1.000 # _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, VHF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ Superbright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 ' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10473 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2596 _reflns_number_gt 2200 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _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 'w=1/[\s^2^(Fo^2^)+(0.0205P)^2^+7.8882P] 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 2596 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0690 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.15002(7) 0.72477(11) 0.13969(7) 0.0333(2) Uani 1 1 d . . . C1 C 0.0287(3) 0.9187(4) 0.1146(3) 0.0295(8) Uani 1 1 d . . . C2 C -0.0266(2) 0.8105(4) 0.0808(2) 0.0242(7) Uani 1 1 d . . . C3 C -0.1243(3) 0.8171(4) 0.0589(2) 0.0282(8) Uani 1 1 d . . . H3 H -0.1624 0.7438 0.0344 0.034 Uiso 1 1 calc R . . C4 C -0.1661(3) 0.9309(4) 0.0730(3) 0.0340(9) Uani 1 1 d . . . H4 H -0.2331 0.9356 0.0584 0.041 Uiso 1 1 calc R . . C5 C -0.1109(3) 1.0372(4) 0.1080(3) 0.0392(10) Uani 1 1 d . . . H5 H -0.1404 1.1147 0.1179 0.047 Uiso 1 1 calc R . . C6 C -0.0131(3) 1.0331(4) 0.1292(3) 0.0415(10) Uani 1 1 d . . . H6 H 0.0247 1.1069 0.1532 0.050 Uiso 1 1 calc R . . C7 C 0.1341(3) 0.8985(4) 0.1330(3) 0.0409(10) Uani 1 1 d . . . H7A H 0.1716 0.9402 0.1908 0.049 Uiso 1 1 calc R . . H7B H 0.1540 0.9348 0.0832 0.049 Uiso 1 1 calc R . . C8 C 0.0280(3) 0.6926(4) 0.0722(3) 0.0339(9) Uani 1 1 d . . . H8A H 0.0226 0.6774 0.0079 0.041 Uiso 1 1 calc R . . H8B H 0.0037 0.6155 0.0954 0.041 Uiso 1 1 calc R . . C9 C 0.1460(3) 0.6985(4) 0.2520(2) 0.0297(8) Uani 1 1 d . . . H9A H 0.2052 0.7293 0.2964 0.045 Uiso 1 1 calc R . . H9B H 0.1385 0.6059 0.2612 0.045 Uiso 1 1 calc R . . H9C H 0.0921 0.7458 0.2598 0.045 Uiso 1 1 calc R . . Se1 Se 0.0000 0.61731(4) 0.7500 0.01941(11) Uani 1 2 d S . . Br1 Br -0.12332(2) 0.62712(4) 0.83635(2) 0.02585(10) Uani 1 1 d . . . Br2 Br 0.13789(2) 0.60157(4) 0.90255(2) 0.02634(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0224(5) 0.0513(6) 0.0275(5) 0.0015(4) 0.0100(4) 0.0043(4) C1 0.0280(19) 0.031(2) 0.028(2) 0.0078(16) 0.0077(17) -0.0037(15) C2 0.0230(17) 0.034(2) 0.0172(17) -0.0005(14) 0.0079(15) 0.0010(15) C3 0.0246(18) 0.033(2) 0.0226(18) 0.0022(15) 0.0023(16) -0.0011(15) C4 0.0255(19) 0.049(3) 0.028(2) 0.0139(18) 0.0099(17) 0.0096(18) C5 0.043(2) 0.033(2) 0.040(2) 0.0061(18) 0.012(2) 0.0142(19) C6 0.048(3) 0.027(2) 0.042(3) 0.0001(18) 0.005(2) -0.0056(18) C7 0.026(2) 0.053(3) 0.043(2) 0.015(2) 0.0101(19) -0.0083(18) C8 0.0266(19) 0.051(3) 0.0211(19) -0.0107(17) 0.0032(16) 0.0040(18) C9 0.0262(19) 0.035(2) 0.0234(19) -0.0057(16) 0.0025(16) -0.0069(16) Se1 0.0155(2) 0.0209(2) 0.0204(2) 0.000 0.00372(19) 0.000 Br1 0.01810(17) 0.0359(2) 0.02379(18) -0.00446(15) 0.00718(14) 0.00132(14) Br2 0.01680(17) 0.0398(2) 0.01942(18) 0.00038(14) 0.00174(14) 0.00199(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C9 1.789(4) . ? S1 C8 1.810(4) . ? S1 C7 1.812(5) . ? C1 C2 1.388(5) . ? C1 C6 1.390(6) . ? C1 C7 1.515(5) . ? C2 C3 1.383(5) . ? C2 C8 1.496(5) . ? C3 C4 1.382(5) . ? C3 H3 0.9500 . ? C4 C5 1.376(6) . ? C4 H4 0.9500 . ? C5 C6 1.385(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? Se1 Br2 2.5915(7) . ? Se1 Br2 2.5915(7) 2_556 ? Se1 Br1 2.6053(7) 2_556 ? Se1 Br1 2.6053(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 S1 C8 101.18(18) . . ? C9 S1 C7 99.3(2) . . ? C8 S1 C7 93.5(2) . . ? C2 C1 C6 120.5(4) . . ? C2 C1 C7 114.2(4) . . ? C6 C1 C7 125.3(4) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 C8 125.2(3) . . ? C1 C2 C8 114.8(3) . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 120.2(4) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 121.0(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 118.6(4) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C1 C7 S1 104.8(3) . . ? C1 C7 H7A 110.8 . . ? S1 C7 H7A 110.8 . . ? C1 C7 H7B 110.8 . . ? S1 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? C2 C8 S1 105.6(3) . . ? C2 C8 H8A 110.6 . . ? S1 C8 H8A 110.6 . . ? C2 C8 H8B 110.6 . . ? S1 C8 H8B 110.6 . . ? H8A C8 H8B 108.7 . . ? S1 C9 H9A 109.5 . . ? S1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? S1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? Br2 Se1 Br2 172.79(3) . 2_556 ? Br2 Se1 Br1 89.69(3) . 2_556 ? Br2 Se1 Br1 90.59(3) 2_556 2_556 ? Br2 Se1 Br1 90.59(3) . . ? Br2 Se1 Br1 89.69(3) 2_556 . ? Br1 Se1 Br1 175.53(3) 2_556 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.022 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.120 data_12aj010ra _database_code_depnum_ccdc_archive 'CCDC 909382' #TrackingRef 'SeX2_all10_1.cif' _audit_creation_method 'SHELXL-97 + hand edit' _audit_creation_date 2012-11-02 _audit_author_name 'Webster, M.' _chemical_name_systematic ; Dichloro(methylsulfanylmethane)selenium(II) ; # Me2S = C2H6S # dimethyl sulphide # methylsulfanylmethane (chemspider) # (Methylsulfanyl)methane (chemspider) # dimethyl sulfide (ACD iLab (defaults)) (NB mostly 'f' rather than 'ph') # (methylthio)methane (ACD iLab (defaults)) (iLab produced two names). _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H6 Cl2 S Se' _chemical_formula_sum 'C2 H6 Cl2 S Se' _chemical_formula_weight 211.99 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' Cl Cl 0.1484 0.1585 '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 monoclinic _symmetry_space_group_name_H-M 'P 21' _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.338(4) _cell_length_b 6.697(4) _cell_length_c 7.977(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.946(7) _cell_angle_gamma 90.00 _cell_volume 335.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1719 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.099 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 6.575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.759 # Expt'l Tmin & Tmax _exptl_absorpt_correction_T_max 1.000 # scaled to Tmax=1.0 _exptl_absorpt_process_details ;Jacobson, R.A. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator ? _diffrn_radiation_collimation 'Confocal mirrors, VHF VariMax ' _diffrn_source 'Rotating anode X-ray tube' _diffrn_source_type 'Rigaku FR-E+ Superbright' _diffrn_measurement_device 'Four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 ' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1733 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0618 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1214 _reflns_number_gt 1161 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.0000P)^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 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 -0.001(8) _chemical_absolute_configuration ad _refine_ls_number_reflns 1214 _refine_ls_number_parameters 57 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0198 _refine_ls_wR_factor_ref 0.0457 _refine_ls_wR_factor_gt 0.0452 _refine_ls_goodness_of_fit_ref 0.734 _refine_ls_restrained_S_all 0.734 _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 Se1 Se 0.66858(4) 0.34499(4) 0.34624(3) 0.01200(8) Uani 1 1 d . . . Cl1 Cl 0.72422(13) 0.23746(12) 0.08012(10) 0.01818(17) Uani 1 1 d . . . Cl2 Cl 0.62048(13) 0.47720(12) 0.63555(10) 0.01889(17) Uani 1 1 d . . . S1 S 0.89125(12) 0.60477(12) 0.33990(10) 0.01439(16) Uani 1 1 d . . . C1 C 0.8076(5) 0.7310(5) 0.1448(4) 0.0210(8) Uani 1 1 d . . . H1A H 0.9118 0.8344 0.1273 0.032 Uiso 1 1 calc R . . H1B H 0.6682 0.7930 0.1486 0.032 Uiso 1 1 calc R . . H1C H 0.7968 0.6350 0.0513 0.032 Uiso 1 1 calc R . . C2 C 1.1371(5) 0.4951(5) 0.3003(4) 0.0160(7) Uani 1 1 d . . . H2A H 1.1105 0.4058 0.2023 0.024 Uiso 1 1 calc R . . H2B H 1.1992 0.4188 0.3999 0.024 Uiso 1 1 calc R . . H2C H 1.2361 0.6007 0.2771 0.024 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 Se1 0.00844(13) 0.01419(14) 0.01341(14) 0.00098(14) 0.00161(9) 0.00054(13) Cl1 0.0196(4) 0.0204(4) 0.0146(4) -0.0032(3) 0.0026(3) -0.0027(3) Cl2 0.0211(4) 0.0203(4) 0.0164(4) 0.0015(3) 0.0066(3) 0.0043(3) S1 0.0123(4) 0.0144(4) 0.0168(4) -0.0012(3) 0.0033(3) -0.0012(3) C1 0.0154(17) 0.0192(18) 0.028(2) 0.0090(15) 0.0020(15) 0.0023(14) C2 0.0089(15) 0.0187(15) 0.0202(17) 0.0043(14) 0.0021(12) 0.0046(13) _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 Se1 S1 2.2453(12) . ? Se1 Cl1 2.3143(13) . ? Se1 Cl2 2.5292(14) . ? S1 C1 1.786(3) . ? S1 C2 1.790(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 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 S1 Se1 Cl1 92.55(3) . . ? S1 Se1 Cl2 84.53(3) . . ? Cl1 Se1 Cl2 177.08(3) . . ? C1 S1 C2 101.62(15) . . ? C1 S1 Se1 105.94(12) . . ? C2 S1 Se1 104.55(13) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Se1 Cl2 3.085(2) . 2_646 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.468 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.104 #===END OF CIF ============================================================== # # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # #===END OF FILE =============================================================