# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Marc Fourmigue' _publ_contact_author_email MARC.FOURMIGUE@UNIV-RENNES1.FR _publ_section_title ; A series of strongly one-dimensional organic metals with strictly uniform stacks: (o-DMTTF)2X (X = Cl, Br, I) ; loop_ _publ_author_name 'Michel Fourmigue' 'Pascale Auban-Senzier' 'Claude Coulon' 'Kim R. Dunbar' 'Claude Pasquier' ; E.Reinheimer ; # Attachment 'oMe2_Br_RT.cif' data_BratRT _database_code_depnum_ccdc_archive 'CCDC 659041' _audit_creation_date 2007-10-31T18:01:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C8 H8 S4), Br' _chemical_formula_sum 'C16 H16 Br S8' _chemical_formula_weight 544.68 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I -4 2 d' _symmetry_space_group_name_Hall 'I -4 2bw' _symmetry_Int_Tables_number 122 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, -z+1/4' '-x, -y, z' '-x, y+1/2, -z+1/4' '-y+1/2, -x, z+3/4' '-y, x, -z' 'y, -x, -z' 'y+1/2, x, z+3/4' 'x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1, -z+3/4' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1, -z+3/4' '-y+1, -x+1/2, z+5/4' '-y+1/2, x+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' 'y+1, x+1/2, z+5/4' _cell_length_a 17.0920(3) _cell_length_b 17.0920(3) _cell_length_c 7.0582(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2061.96(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10744 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.755 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1100 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.02 -18 1 1 0.032 1 5 7 0.148 -2 -2 -3 0.116 -2 19 1 0.036 2 -14 -1 0.095 -3 0 1 0.07 2 1 -1 0.113 -2 -1 0 0.029 2 1 0 0.016 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.803 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.6393 _exptl_absorpt_correction_T_max 0.8301 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.323633E-1 _diffrn_orient_matrix_ub_12 0.257479E-1 _diffrn_orient_matrix_ub_13 0.100217 _diffrn_orient_matrix_ub_21 0.16984E-2 _diffrn_orient_matrix_ub_22 -0.502427E-1 _diffrn_orient_matrix_ub_23 0.724795E-1 _diffrn_orient_matrix_ub_31 0.487113E-1 _diffrn_orient_matrix_ub_32 -0.153549E-1 _diffrn_orient_matrix_ub_33 -0.691104E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_av_unetI/netI 0.0234 _diffrn_reflns_number 17533 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 1191 _reflns_number_gt 1123 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0269P)^2^+0.9713P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0022(3) _refine_ls_number_reflns 1191 _refine_ls_number_parameters 61 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.024 _refine_ls_wR_factor_ref 0.0596 _refine_ls_wR_factor_gt 0.0578 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.378(12) _refine_diff_density_max 0.251 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.61878(3) 0.16385(3) 0.13492(9) 0.03321(15) Uani 1 1 d . . . S2 S 0.80782(4) 0.33526(3) 0.12805(10) 0.03430(15) Uani 1 1 d . . . C1 C 0.67293(17) 0.25 0.125 0.0278(6) Uani 1 2 d S . . C3 C 0.89930(12) 0.28924(14) 0.1278(4) 0.0359(5) Uani 1 1 d . . . C4 C 0.52911(13) 0.21121(14) 0.1307(4) 0.0388(5) Uani 1 1 d . . . H4 H 0.4825 0.1832 0.1362 0.047 Uiso 1 1 calc R . . C2 C 0.75280(18) 0.25 0.125 0.0279(6) Uani 1 2 d S . . C5 C 0.96884(16) 0.34277(17) 0.1317(5) 0.0510(7) Uani 1 1 d . . . H5A H 1.0158 0.3126 0.1175 0.077 Uiso 1 1 calc R . . H5B H 0.9702 0.3702 0.2504 0.077 Uiso 1 1 calc R . . H5C H 0.965 0.3798 0.0299 0.077 Uiso 1 1 calc R . . Br1 Br 0.5 0 0.25 0.04593(16) Uani 1 4 d S . . 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 0.0314(3) 0.0278(3) 0.0404(3) 0.0000(3) -0.0011(3) -0.0036(2) S2 0.0325(3) 0.0269(3) 0.0435(3) 0.0026(3) -0.0015(2) -0.0042(2) C1 0.0294(14) 0.0238(13) 0.0301(14) -0.0024(13) 0 0 C3 0.0280(10) 0.0458(13) 0.0341(12) 0.0105(12) -0.0014(11) -0.0041(9) C4 0.0274(10) 0.0464(12) 0.0426(13) 0.0028(13) 0.0001(11) -0.0071(9) C2 0.0276(13) 0.0247(12) 0.0314(15) -0.0007(12) 0 0 C5 0.0367(12) 0.0658(18) 0.0505(15) 0.0179(16) -0.0052(13) -0.0172(11) Br1 0.03842(18) 0.03842(18) 0.0610(3) 0 0 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C4 1.733(2) . ? S1 C1 1.7406(17) . ? S2 C2 1.7346(18) . ? S2 C3 1.750(2) . ? C1 C2 1.365(4) . ? C1 S1 1.7406(17) 2 ? C3 C3 1.342(5) 2 ? C3 C5 1.500(3) . ? C4 C4 1.329(5) 2 ? C2 S2 1.7346(18) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C1 94.27(11) . . ? C2 S2 C3 96.13(12) . . ? C2 C1 S1 122.12(8) . . ? C2 C1 S1 122.12(8) . 2 ? S1 C1 S1 115.75(17) . 2 ? C3 C3 C5 127.60(16) 2 . ? C3 C3 S2 116.70(8) 2 . ? C5 C3 S2 115.7(2) . . ? C4 C4 S1 117.85(8) 2 . ? C1 C2 S2 122.83(9) . . ? C1 C2 S2 122.83(9) . 2 ? S2 C2 S2 114.33(18) . 2 ? # Attachment 'oMe2_Cl_RT.cif' data_ChlorideRT _database_code_depnum_ccdc_archive 'CCDC 659042' _audit_creation_date 2007-07-11T14:59:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C8 H8 S4), Cl1' _chemical_formula_sum 'C16 H16 Cl S8' _chemical_formula_weight 500.22 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I -4 2 d' _symmetry_space_group_name_Hall 'I -4 2bw' _symmetry_Int_Tables_number 122 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, -z+1/4' '-x, -y, z' '-x, y+1/2, -z+1/4' '-y+1/2, -x, z+3/4' '-y, x, -z' 'y, -x, -z' 'y+1/2, x, z+3/4' 'x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1, -z+3/4' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1, -z+3/4' '-y+1, -x+1/2, z+5/4' '-y+1/2, x+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' 'y+1, x+1/2, z+5/4' _cell_length_a 16.9376(6) _cell_length_b 16.9376(6) _cell_length_c 7.0400(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2019.65(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11121 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1028 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.02 -1 0 0 0.015 1 -12 -12 0.089 -14 13 13 0.097 0 1 0 0.022 0 -1 0 0.015 0 0 1 0.099 -1 3 0 0.015 1 -3 0 0.013 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.016 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.8069 _exptl_absorpt_correction_T_max 1.1853 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.504813E-1 _diffrn_orient_matrix_ub_12 -0.57879E-2 _diffrn_orient_matrix_ub_13 -0.723331E-1 _diffrn_orient_matrix_ub_21 0.59666E-2 _diffrn_orient_matrix_ub_22 -0.550043E-1 _diffrn_orient_matrix_ub_23 0.04958 _diffrn_orient_matrix_ub_31 -0.300298E-1 _diffrn_orient_matrix_ub_32 -0.206585E-1 _diffrn_orient_matrix_ub_33 -0.111744 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.1299 _diffrn_reflns_av_unetI/netI 0.0471 _diffrn_reflns_number 14655 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 1161 _reflns_number_gt 1010 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. Positions of the hydrogen atoms, first identified in the Fourier difference map, were calculated using the HFIX 43 for the sp2 H atom, but HFIX 137 for the methyl H atoms. In this approach, a difference electron density synthesis is calculated around the circle which represents the locus of possible hydrogen positions (for a fixed X-H distance and Y-X-H angle). The maximum electron densityis then taken as the starting position for the hydrogen atoms. In subsequent refinement cycles (and in further least-squares jobs) the hydrogens are re-idealized at the start of each cycle, but the current torsion angle is retained;the torsion angles are allowed to refine whilst keeping the X-H distance and Y-X-H angle fixed. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+3.5107P] 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_number_reflns 1161 _refine_ls_number_parameters 60 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(2) _refine_diff_density_max 0.491 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.115 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.38314(4) 0.33694(5) 0.11459(12) 0.0352(2) Uani 1 1 d . . . S2 S 0.19241(4) 0.16403(4) 0.12304(13) 0.0353(2) Uani 1 1 d . . . C1 C 0.3282(2) 0.25 0.125 0.0304(8) Uani 1 2 d S . . C3 C 0.10004(16) 0.2105(2) 0.1236(5) 0.0363(6) Uani 1 1 d . . . C4 C 0.47334(16) 0.2889(2) 0.1194(5) 0.0401(7) Uani 1 1 d . . . H4 H 0.5204 0.3171 0.1142 0.048 Uiso 1 1 calc R . . C2 C 0.2477(3) 0.25 0.125 0.0291(7) Uani 1 2 d S . . C5 C 0.0299(2) 0.1560(2) 0.1205(6) 0.0483(9) Uani 1 1 d . . . H5A H -0.0177 0.1864 0.1331 0.073 Uiso 1 1 calc R . . H5B H 0.0337 0.1193 0.2239 0.073 Uiso 1 1 calc R . . H5C H 0.0289 0.1277 0.0024 0.073 Uiso 1 1 calc R . . Cl1 Cl 0.5 0.5 0 0.0568(5) Uani 1 4 d S . . 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 0.0334(4) 0.0331(4) 0.0391(4) -0.0003(4) -0.0009(4) -0.0047(3) S2 0.0333(4) 0.0298(3) 0.0429(4) 0.0024(4) -0.0010(4) -0.0036(3) C1 0.0339(19) 0.0294(18) 0.0280(19) 0.0000(19) 0 0 C3 0.0285(13) 0.0468(16) 0.0336(14) 0.0078(17) -0.0018(15) -0.0023(12) C4 0.0276(13) 0.0524(17) 0.0403(16) 0.0028(19) 0.0028(15) -0.0052(13) C2 0.0291(17) 0.0292(17) 0.0290(18) -0.0003(18) 0 0 C5 0.0377(16) 0.061(2) 0.047(2) 0.015(2) -0.0033(18) -0.0147(15) Cl1 0.0514(7) 0.0514(7) 0.0677(13) 0 0 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C4 1.731(3) . ? S1 C1 1.744(2) . ? S2 C2 1.731(2) . ? S2 C3 1.751(3) . ? C1 C2 1.364(6) . ? C1 S1 1.744(2) 2 ? C3 C3 1.339(7) 2 ? C3 C5 1.504(4) . ? C4 C4 1.320(7) 2 ? C2 S2 1.731(2) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C1 94.21(16) . . ? C2 S2 C3 96.04(16) . . ? C2 C1 S1 122.27(12) . 2 ? C2 C1 S1 122.27(12) . . ? S1 C1 S1 115.5(2) 2 . ? C3 C3 C5 127.83(19) 2 . ? C3 C3 S2 116.70(11) 2 . ? C5 C3 S2 115.5(2) . . ? C4 C4 S1 118.05(11) 2 . ? C1 C2 S2 122.74(12) . . ? C1 C2 S2 122.74(12) . 2 ? S2 C2 S2 114.5(2) . 2 ? # Attachment 'oMe2_I_RT.cif' data_IatRT _database_code_depnum_ccdc_archive 'CCDC 659046' _audit_creation_date 2007-10-30T16:34:01-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C8 H8 S4), I' _chemical_formula_sum 'C16 H16 I S8' _chemical_formula_weight 591.67 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I -4 2 d' _symmetry_space_group_name_Hall 'I -4 2bw' _symmetry_Int_Tables_number 122 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, -z+1/4' '-x, -y, z' '-x, y+1/2, -z+1/4' '-y+1/2, -x, z+3/4' '-y, x, -z' 'y, -x, -z' 'y+1/2, x, z+3/4' 'x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1, -z+3/4' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1, -z+3/4' '-y+1, -x+1/2, z+5/4' '-y+1/2, x+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' 'y+1, x+1/2, z+5/4' _cell_length_a 17.4031(2) _cell_length_b 17.4031(2) _cell_length_c 7.09780(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2149.70(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10091 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.828 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.053 -1 0 0 0.088 0 -4 -1 0.248 0 4 1 0.278 0 -1 0 0.068 0 1 0 0.075 -3 0 1 0.308 3 0 -1 0.293 -4 -2 -5 0.371 3 2 -4 0.393 2 1 17 0.338 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.3534 _exptl_absorpt_correction_T_max 0.892 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.324243E-1 _diffrn_orient_matrix_ub_12 0.15241E-1 _diffrn_orient_matrix_ub_13 -0.110149 _diffrn_orient_matrix_ub_21 0.393744E-1 _diffrn_orient_matrix_ub_22 0.389965E-1 _diffrn_orient_matrix_ub_23 -0.372415E-1 _diffrn_orient_matrix_ub_31 0.264593E-1 _diffrn_orient_matrix_ub_32 -0.393542E-1 _diffrn_orient_matrix_ub_33 -0.795611E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0852 _diffrn_reflns_av_unetI/netI 0.0281 _diffrn_reflns_number 14532 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.41 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 1226 _reflns_number_gt 1197 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+1.5432P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0066(5) _refine_ls_number_reflns 1226 _refine_ls_number_parameters 61 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0584 _refine_ls_wR_factor_gt 0.0575 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.050 _refine_ls_shift/su_mean 0.046 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_diff_density_max 0.326 _refine_diff_density_min -0.665 _refine_diff_density_rms 0.065 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.62275(3) 0.16537(3) 0.13423(9) 0.03422(16) Uani 1 1 d . . . S2 S 0.80850(4) 0.33367(4) 0.13007(10) 0.03695(16) Uani 1 1 d . . . C1 C 0.67608(18) 0.25 0.125 0.0295(6) Uani 1 2 d S . . C3 C 0.89831(15) 0.28875(16) 0.1294(4) 0.0405(6) Uani 1 1 d . . . C4 C 0.53486(15) 0.21176(15) 0.1302(4) 0.0406(5) Uani 1 1 d . . . H4 H 0.4891 0.1842 0.1351 0.049 Uiso 1 1 calc R . . C2 C 0.7546(2) 0.25 0.125 0.0295(7) Uani 1 2 d S . . C5 C 0.96673(19) 0.3410(2) 0.1365(5) 0.0597(8) Uani 1 1 d . . . H5A H 1.0129 0.3109 0.1318 0.09 Uiso 1 1 calc R . . H5B H 0.9657 0.3701 0.2514 0.09 Uiso 1 1 calc R . . H5C H 0.9654 0.3754 0.0309 0.09 Uiso 1 1 calc R . . I1 I 0.5 0 0.25 0.04331(14) Uani 1 4 d S . . 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 0.0354(3) 0.0270(3) 0.0403(3) -0.0003(3) -0.0006(2) -0.0027(2) S2 0.0383(3) 0.0295(3) 0.0431(3) 0.0038(3) -0.0023(3) -0.0057(2) C1 0.0333(15) 0.0251(14) 0.0300(13) 0.0002(12) 0 0 C3 0.0339(12) 0.0535(15) 0.0340(10) 0.0161(12) -0.0032(11) -0.0048(10) C4 0.0337(12) 0.0434(13) 0.0447(12) 0.0035(12) 0.0017(13) -0.0057(10) C2 0.0324(15) 0.0255(13) 0.0305(14) 0.0020(12) 0 0 C5 0.0428(15) 0.079(2) 0.0576(16) 0.0232(18) -0.0083(15) -0.0223(14) I1 0.03415(15) 0.03415(15) 0.0616(2) 0 0 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C4 1.730(3) . ? S1 C1 1.7421(18) . ? S2 C2 1.732(2) . ? S2 C3 1.748(3) . ? C1 C2 1.367(5) . ? C1 S1 1.7421(18) 2 ? C3 C3 1.350(6) 2 ? C3 C5 1.499(4) . ? C4 C4 1.333(5) 2 ? C4 H4 0.93 . ? C2 S2 1.732(2) 2 ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? 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 C4 S1 C1 94.35(12) . . ? C2 S2 C3 96.19(14) . . ? C2 C1 S1 122.19(9) . . ? C2 C1 S1 122.19(9) . 2 ? S1 C1 S1 115.62(18) . 2 ? C3 C3 C5 127.4(2) 2 . ? C3 C3 S2 116.55(9) 2 . ? C5 C3 S2 116.1(2) . . ? C4 C4 S1 117.84(8) 2 . ? C4 C4 H4 121.1 2 . ? S1 C4 H4 121.1 . . ? C1 C2 S2 122.76(10) . . ? C1 C2 S2 122.76(10) . 2 ? S2 C2 S2 114.5(2) . 2 ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ?