# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1842 data_global _publ_contact_author_name 'Lyall R. Hanton' _publ_contact_author_address ; 'Department of Chemistry University of Otago PO Box 56 Dunedin NZ' ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; 'Thiophene S-binding of a conformationally constrained thiophenophane leading to the formation of a copper (I) coordination polymer' ; data_C13H13NS3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N S3' _chemical_formula_sum 'C13 H13 N S3' _chemical_formula_weight 279.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.768(5) _cell_length_b 15.464(5) _cell_length_c 15.529(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 2585.8(17) _cell_formula_units_Z 8 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 1312 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 26.28 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.549 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8566 _exptl_absorpt_correction_T_max 0.957 _exptl_absorpt_process_details 'SADABS (Sheldrick 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6628 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 26.28 _reflns_number_total 1312 _reflns_number_gt 959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R- factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1312 _refine_ls_number_parameters 154 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0680 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0621(4) 0.26221(18) 0.23016(17) 0.0190(14) Uani 1 1 d . . . C2 C 1.1663(4) 0.21518(19) 0.25169(19) 0.0271(15) Uani 1 1 d . . . H2 H 1.2276 0.2391 0.2865 0.032 Uiso 1 1 calc R . . C3 C 1.1783(4) 0.1312(2) 0.2204(2) 0.0380(15) Uani 1 1 d . . . H3 H 1.2468 0.0975 0.2347 0.046 Uiso 1 1 calc R . . C4 C 1.0855(4) 0.0992(2) 0.1672(2) 0.0306(16) Uani 1 1 d . . . H4 H 1.0916 0.0436 0.1448 0.037 Uiso 1 1 calc R . . C5 C 0.9847(4) 0.1500(2) 0.14770(17) 0.0216(14) Uani 1 1 d . . . C6 C 0.8853(4) 0.11944(19) 0.08751(17) 0.0295(13) Uani 1 1 d . . . H6A H 0.8119 0.1549 0.0956 0.035 Uiso 1 1 calc R . . H6B H 0.8634 0.0604 0.1022 0.035 Uiso 1 1 calc R . . C7 C 0.8604(4) 0.22415(17) -0.06511(18) 0.0259(12) Uani 1 1 d . . . H7A H 0.8913 0.2356 -0.1227 0.031 Uiso 1 1 calc R . . H7B H 0.7714 0.2155 -0.0695 0.031 Uiso 1 1 calc R . . C8 C 0.8835(4) 0.30214(19) -0.01081(18) 0.0233(11) Uani 1 1 d U . . C9 C 0.7989(4) 0.34861(19) 0.03455(18) 0.0304(11) Uani 1 1 d U . . H9 H 0.7140 0.3377 0.0332 0.036 Uiso 1 1 calc R . . C10 C 0.8537(6) 0.4161(2) 0.0846(2) 0.026(3) Uani 1 1 d . . . H10 H 0.8076 0.4531 0.1193 0.031 Uiso 1 1 calc R . . C11 C 0.9784(6) 0.4214(2) 0.0770(2) 0.021(2) Uani 1 1 d . . . C12 C 1.0646(4) 0.47970(18) 0.12458(18) 0.0327(13) Uani 1 1 d . . . H12A H 1.0161 0.5239 0.1534 0.039 Uiso 1 1 calc R . . H12B H 1.1181 0.5085 0.0833 0.039 Uiso 1 1 calc R . . C13 C 1.0508(3) 0.35585(16) 0.26046(17) 0.0270(12) Uani 1 1 d . . . H13A H 1.0660 0.3587 0.3220 0.032 Uiso 1 1 calc R . . H13B H 0.9671 0.3764 0.2498 0.032 Uiso 1 1 calc R . . N1 N 0.9700(3) 0.23145(14) 0.18038(15) 0.0207(9) Uani 1 1 d U . . S1 S 0.93082(11) 0.12348(5) -0.02639(5) 0.0349(5) Uani 1 1 d . . . S2 S 1.03191(12) 0.34214(5) 0.00651(5) 0.0272(5) Uani 1 1 d . . . S3 S 1.16179(11) 0.42549(5) 0.20436(5) 0.0309(5) 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 C1 0.015(5) 0.0273(17) 0.0146(15) 0.0038(12) 0.003(2) 0.000(2) C2 0.021(5) 0.0334(18) 0.0267(16) 0.0010(15) -0.006(2) -0.001(2) C3 0.041(5) 0.0319(18) 0.0415(19) 0.0003(15) -0.014(2) 0.009(2) C4 0.032(6) 0.0259(17) 0.0344(19) -0.0020(15) -0.006(2) 0.002(3) C5 0.014(5) 0.0308(18) 0.0201(15) 0.0032(14) 0.0026(19) -0.007(2) C6 0.029(4) 0.0325(17) 0.0270(16) 0.0005(14) 0.002(2) -0.009(2) C7 0.012(4) 0.0393(18) 0.0267(16) -0.0003(14) 0.000(2) -0.004(2) C8 0.018(3) 0.0296(14) 0.0224(14) 0.0013(12) -0.0007(17) 0.0007(19) C9 0.023(3) 0.0403(16) 0.0279(14) 0.0022(14) -0.0020(18) 0.000(2) C10 0.022(8) 0.0298(18) 0.0272(16) 0.0004(14) 0.004(3) 0.010(4) C11 0.014(8) 0.0248(17) 0.0240(17) 0.0042(13) -0.001(3) -0.002(4) C12 0.041(4) 0.0260(16) 0.0308(17) 0.0053(13) -0.008(2) -0.001(2) C13 0.030(4) 0.0300(16) 0.0206(15) 0.0015(13) 0.003(2) 0.0003(19) N1 0.015(3) 0.0286(13) 0.0189(12) 0.0013(10) 0.0017(15) -0.0020(15) S1 0.0482(16) 0.0329(5) 0.0236(4) -0.0048(3) 0.0006(5) -0.0005(6) S2 0.0258(16) 0.0296(4) 0.0261(4) -0.0002(3) -0.0004(5) -0.0009(6) S3 0.0315(13) 0.0291(4) 0.0322(4) 0.0048(3) -0.0038(5) -0.0064(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.344(4) . ? C1 C2 1.379(4) . ? C1 C13 1.527(4) . ? C2 C3 1.393(4) . ? C3 C4 1.387(5) . ? C4 C5 1.373(5) . ? C5 N1 1.367(4) . ? C5 C6 1.498(5) . ? C6 S1 1.837(3) . ? C7 C8 1.493(4) . ? C7 S1 1.833(3) . ? C8 C9 1.357(5) . ? C8 S2 1.735(4) . ? C9 C10 1.429(5) . ? C10 C11 1.350(5) . ? C11 C12 1.490(5) . ? C11 S2 1.741(4) . ? C12 S3 1.825(3) . ? C13 S3 1.829(3) . ? 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 N1 C1 C2 123.6(3) . . ? N1 C1 C13 117.0(4) . . ? C2 C1 C13 119.3(3) . . ? C1 C2 C3 118.9(4) . . ? C4 C3 C2 118.2(4) . . ? C5 C4 C3 119.8(3) . . ? N1 C5 C4 122.4(3) . . ? N1 C5 C6 116.1(4) . . ? C4 C5 C6 121.5(3) . . ? C5 C6 S1 113.5(3) . . ? C8 C7 S1 115.6(2) . . ? C9 C8 C7 127.5(4) . . ? C9 C8 S2 110.4(3) . . ? C7 C8 S2 122.0(3) . . ? C8 C9 C10 113.1(4) . . ? C11 C10 C9 114.1(4) . . ? C10 C11 C12 127.8(4) . . ? C10 C11 S2 110.0(3) . . ? C12 C11 S2 122.1(4) . . ? C11 C12 S3 114.5(2) . . ? C1 C13 S3 111.1(2) . . ? C1 N1 C5 117.0(3) . . ? C7 S1 C6 103.54(15) . . ? C8 S2 C11 92.5(2) . . ? C12 S3 C13 102.66(16) . . ? _diffrn_measured_fraction_theta_max 0.500 _diffrn_reflns_theta_full 26.28 _diffrn_measured_fraction_theta_full 0.500 _refine_diff_density_max 0.341 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.040 #===END data_[Cu(C13H13NS3)](BF4) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 Cu F6 N P S3' _chemical_formula_sum 'C13 H13 Cu F6 N P S3' _chemical_formula_weight 487.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C11' 0.0020 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' _cell_length_a 10.727(5) _cell_length_b 21.194(9) _cell_length_c 7.553(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1717.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 1986 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.41 _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.888 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 1.787 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3642 _exptl_absorpt_correction_T_max 0.6695 _exptl_absorpt_process_details 'SADABS (Sheldrick 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20131 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.41 _reflns_number_total 1986 _reflns_number_gt 1886 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R- factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+25.5495P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1986 _refine_ls_number_parameters 184 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0876 _refine_ls_wR_factor_ref 0.1818 _refine_ls_wR_factor_gt 0.1809 _refine_ls_goodness_of_fit_ref 1.314 _refine_ls_restrained_S_all 1.299 _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 Cu1 Cu 0.65702(11) 0.18002(6) 0.5000 0.0250(3) Uani 1 2 d S . . S2 S 1.0734(2) 0.22564(11) 0.5000 0.0229(5) Uani 1 2 d S . . S3 S 0.5513(2) 0.08311(13) 0.5000 0.0311(6) Uani 1 2 d S . . C10 C 0.6335(6) 0.0500(3) 0.3129(11) 0.0306(17) Uani 1 1 d . . . H10A H 0.6499 0.0046 0.3345 0.037 Uiso 1 1 calc R A 1 H10B H 0.5812 0.0535 0.2054 0.037 Uiso 1 1 calc R A 1 N1 N 0.7841(9) 0.1402(4) 0.3378(15) 0.012(2) Uani 0.50 1 d PU . 1 C2 C 0.751(2) 0.0829(12) 0.285(4) 0.025(6) Uani 0.50 1 d PU . 1 C3 C 0.8400(14) 0.0486(6) 0.178(2) 0.027(3) Uani 0.50 1 d P . 1 H3 H 0.8213 0.0070 0.1397 0.033 Uiso 0.50 1 calc PR . 1 C4 C 0.9519(14) 0.0758(7) 0.132(2) 0.028(3) Uani 0.50 1 d P . 1 H4 H 1.0081 0.0541 0.0564 0.034 Uiso 0.50 1 calc PR . 1 C5 C 0.9823(14) 0.1353(7) 0.197(2) 0.026(3) Uani 0.50 1 d PU . 1 H5 H 1.0601 0.1544 0.1698 0.031 Uiso 0.50 1 calc PR . 1 C6 C 0.8963(12) 0.1655(6) 0.3021(17) 0.012(3) Uani 0.50 1 d PU . 1 C11 C11 0.9292(12) 0.2292(6) 0.3801(18) 0.019(3) Uani 0.50 1 d P . 1 H11A H 0.8617 0.2431 0.4606 0.022 Uiso 0.50 1 calc PR . 1 H11B H 0.9364 0.2607 0.2837 0.022 Uiso 0.50 1 calc PR . 1 S1' S 0.7820(3) 0.15242(16) 0.2235(5) 0.0225(7) Uani 0.50 1 d P . 2 C2' C 0.9394(14) 0.1490(6) 0.279(2) 0.014(2) Uani 0.50 1 d PU . 2 C3' C 0.9721(13) 0.0902(7) 0.3203(18) 0.024(3) Uani 0.50 1 d PU . 2 H3' H 1.0564 0.0787 0.3419 0.028 Uiso 0.50 1 calc PR . 2 C4' C 0.8740(14) 0.0462(7) 0.330(2) 0.032(3) Uani 0.50 1 d P . 2 H4' H 0.8814 0.0038 0.3702 0.039 Uiso 0.50 1 calc PR . 2 C5' C 0.768(2) 0.0737(10) 0.274(3) 0.011(5) Uani 0.50 1 d PU . 2 C12 C 1.0163(13) 0.2087(6) 0.2733(18) 0.022(3) Uani 0.50 1 d PU . 2 H12A H 0.9649 0.2442 0.2300 0.026 Uiso 0.50 1 calc PR . 2 H12B H 1.0878 0.2032 0.1918 0.026 Uiso 0.50 1 calc PR . 2 P1 P 0.3486(3) 0.13125(14) 0.0000 0.0325(7) Uani 1 2 d S . . F5 F 0.4039(7) 0.0615(3) 0.0000 0.053(2) Uani 1 2 d S . .