# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2013 ####################################################################### # # 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_(BTBT)2PF6_ #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C28 H16 F6 P S4' _chemical_formula_moiety 'C28 H16 F6 P S4' _chemical_formula_weight 625.64 _chemical_melting_point ? _chemical_absolute_configuration ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P -4 21 c' _symmetry_space_group_name_Hall 'P -4 2n' _symmetry_Int_Tables_number 114 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 +Y,-X,-Z 3 -X,-Y,+Z 4 -Y,+X,-Z 5 1/2-X,1/2+Y,1/2-Z 6 1/2-Y,1/2-X,1/2+Z 7 1/2+X,1/2-Y,1/2-Z 8 1/2+Y,1/2+X,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 13.4896(14) _cell_length_b 13.4896(14) _cell_length_c 6.7343(18) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1225.4(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.39 _cell_measurement_theta_max 16.92 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 634.00 _exptl_absorpt_coefficient_mu 0.519 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 0.901 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 298 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 1411 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 4 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.059 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1120 _reflns_number_gt 718 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1368 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 1120 _refine_ls_number_parameters 89 _refine_ls_goodness_of_fit_ref 0.854 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.390 _refine_diff_density_min -0.300 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 87 Friedel Pairs' _refine_ls_abs_structure_Flack 1.1(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; C C 0.0033 0.0016 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; P P 0.1023 0.0942 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 1.04020(8) 0.34999(7) 0.0998(3) 0.0294(3) Uani 1.0 8 d . . . P1 P 1.0000 0.0000 0.0000 0.0425(7) Uani 1.0 2 d . . . F1 F 1.0000 0.0000 0.2348(11) 0.097(2) Uani 1.0 4 d . . . F2 F 1.0308(3) 0.1136(3) 0.0001(6) 0.0753(13) Uani 1.0 8 d . . . C1 C 0.8466(4) 0.2744(4) 0.0999(9) 0.0339(10) Uani 1.0 8 d . . . C2 C 0.7452(4) 0.2940(4) 0.1016(9) 0.0395(11) Uani 1.0 8 d . . . C3 C 0.7081(3) 0.3901(4) 0.1017(10) 0.0373(10) Uani 1.0 8 d . . . C4 C 0.7704(3) 0.4699(4) 0.1031(9) 0.0340(10) Uani 1.0 8 d . . . C5 C 0.8733(3) 0.4535(3) 0.1017(8) 0.0280(9) Uani 1.0 8 d . . . C6 C 0.9092(3) 0.3553(3) 0.1014(8) 0.0282(9) Uani 1.0 8 d . . . C7 C 1.0469(3) 0.4774(3) 0.1015(8) 0.0272(9) Uani 1.0 8 d . . . H1 H 0.8708 0.2099 0.0980 0.0407 Uiso 1.0 8 calc R . . H2 H 0.7010 0.2412 0.1026 0.0475 Uiso 1.0 8 calc R . . H3 H 0.6399 0.4002 0.1009 0.0448 Uiso 1.0 8 calc R . . H4 H 0.7452 0.5341 0.1050 0.0408 Uiso 1.0 8 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0279(6) 0.0273(6) 0.0330(5) 0.0041(4) -0.0000(6) -0.0001(6) P1 0.0331(9) 0.0331(9) 0.061(2) 0.0000 0.0000 0.0000 F1 0.101(5) 0.124(6) 0.067(4) -0.038(5) 0.0000 0.0000 F2 0.053(2) 0.0349(17) 0.138(4) -0.0044(14) 0.017(2) 0.001(3) C1 0.039(3) 0.032(2) 0.031(2) 0.0005(19) -0.002(3) -0.002(3) C2 0.039(3) 0.045(3) 0.035(3) -0.010(2) 0.005(3) -0.006(3) C3 0.027(3) 0.047(3) 0.038(3) -0.0020(18) 0.004(3) -0.002(3) C4 0.028(2) 0.041(3) 0.032(2) 0.0072(18) -0.001(3) -0.001(3) C5 0.0284(19) 0.031(2) 0.0249(19) 0.0014(16) -0.001(3) 0.002(3) C6 0.029(2) 0.033(3) 0.0227(18) 0.0029(16) 0.000(2) 0.002(3) C7 0.032(2) 0.024(2) 0.025(2) 0.0034(16) -0.004(2) -0.002(2) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction WinAFC _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 C6 1.768(5) yes . . S1 C7 1.720(4) yes . . P1 F1 1.581(8) yes . . P1 F1 1.581(8) yes . 2_665 P1 F2 1.588(4) yes . . P1 F2 1.588(4) yes . 2_665 P1 F2 1.588(4) yes . 3_755 P1 F2 1.588(4) yes . 4_645 C1 C2 1.392(7) yes . . C1 C6 1.381(6) yes . . C2 C3 1.389(7) yes . . C3 C4 1.367(7) yes . . C4 C5 1.406(6) yes . . C5 C6 1.410(6) yes . . C5 C7 1.424(6) yes . 3_765 C7 C7 1.405(6) yes . 3_765 C1 H1 0.930 no . . C2 H2 0.930 no . . C3 H3 0.930 no . . C4 H4 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C6 S1 C7 90.69(19) yes . . . F1 P1 F1 180.000 yes . . 2_665 F1 P1 F2 89.99(15) yes . . . F1 P1 F2 90.01(15) yes . . 2_665 F1 P1 F2 89.99(15) yes . . 3_755 F1 P1 F2 90.01(15) yes . . 4_645 F1 P1 F2 90.01(15) yes 2_665 . . F1 P1 F2 89.99(15) yes 2_665 . 2_665 F1 P1 F2 90.01(15) yes 2_665 . 3_755 F1 P1 F2 89.99(15) yes 2_665 . 4_645 F2 P1 F2 90.00(16) yes . . 2_665 F2 P1 F2 180.0(2) yes . . 3_755 F2 P1 F2 90.00(16) yes . . 4_645 F2 P1 F2 90.00(16) yes 2_665 . 3_755 F2 P1 F2 180.0(2) yes 2_665 . 4_645 F2 P1 F2 90.00(16) yes 3_755 . 4_645 C2 C1 C6 116.8(4) yes . . . C1 C2 C3 122.1(5) yes . . . C2 C3 C4 120.9(4) yes . . . C3 C4 C5 118.9(4) yes . . . C4 C5 C6 119.1(4) yes . . . C4 C5 C7 130.0(4) yes . . 3_765 C6 C5 C7 110.9(4) yes . . 3_765 S1 C6 C1 125.4(4) yes . . . S1 C6 C5 112.4(3) yes . . . C1 C6 C5 122.2(4) yes . . . S1 C7 C5 133.9(4) yes . . 3_765 S1 C7 C7 112.8(3) yes . . 3_765 C5 C7 C7 113.3(4) yes 3_765 . 3_765 C2 C1 H1 121.629 no . . . C6 C1 H1 121.617 no . . . C1 C2 H2 118.937 no . . . C3 C2 H2 118.930 no . . . C2 C3 H3 119.556 no . . . C4 C3 H3 119.545 no . . . C3 C4 H4 120.558 no . . . C5 C4 H4 120.563 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C6 S1 C7 C5 179.9(5) no . . . 3_765 C6 S1 C7 C7 -0.5(4) no . . . 3_765 C7 S1 C6 C1 179.6(5) no . . . . C7 S1 C6 C5 0.4(4) no . . . . C2 C1 C6 S1 180.0(5) no . . . . C2 C1 C6 C5 -0.9(8) no . . . . C6 C1 C2 C3 0.9(8) no . . . . C1 C2 C3 C4 -0.9(9) no . . . . C2 C3 C4 C5 0.9(9) no . . . . C3 C4 C5 C6 -0.8(8) no . . . . C3 C4 C5 C7 179.6(6) no . . . 3_765 C4 C5 C6 S1 -179.9(5) no . . . . C4 C5 C6 C1 0.8(8) no . . . . C4 C5 C7 S1 -0.9(10) no . . 3_765 3_765 C4 C5 C7 C7 179.5(6) no . . 3_765 . C6 C5 C7 S1 179.4(5) no . . 3_765 3_765 C6 C5 C7 C7 -0.1(7) no . . 3_765 . C7 C5 C6 S1 -0.2(6) no 3_765 . . . C7 C5 C6 C1 -179.5(5) no 3_765 . . . S1 C7 C7 S1 -179.2(3) no . . 3_765 3_765 S1 C7 C7 C5 0.5(6) no . . 3_765 . C5 C7 C7 S1 0.5(6) no 3_765 . 3_765 3_765 C5 C7 C7 C5 -179.9(4) no 3_765 . 3_765 . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 S1 C4 3.525(5) no . 3_765 C1 C4 2.831(7) no . . C2 C5 2.759(7) no . . C3 C6 2.753(6) no . . S1 F2 3.261(4) no . . S1 C5 3.567(6) no . 8_544 S1 C5 3.590(6) no . 8_545 F1 F1 3.572(11) no . 2_666 F1 C3 3.360(6) no . 5_645 F1 C3 3.360(6) no . 7_555 F2 S1 3.261(4) no . . F2 C1 3.366(6) no . . F2 C1 3.397(6) no . 2_665 F2 C3 3.594(7) no . 7_555 F2 C3 3.524(7) no . 8_544 F2 C4 3.506(7) no . 8_544 C1 F2 3.366(6) no . . C1 F2 3.397(6) no . 4_645 C1 C2 3.452(8) no . 8_544 C1 C2 3.474(8) no . 8_545 C1 C3 3.521(9) no . 8_544 C1 C3 3.545(9) no . 8_545 C2 C1 3.474(8) no . 8_544 C2 C1 3.452(8) no . 8_545 C2 C2 3.494(8) no . 8_544 C2 C2 3.494(8) no . 8_545 C3 F1 3.360(6) no . 5_655 C3 F2 3.594(7) no . 7_455 C3 F2 3.524(7) no . 8_545 C3 C1 3.545(9) no . 8_544 C3 C1 3.521(9) no . 8_545 C4 F2 3.506(7) no . 8_545 C5 S1 3.590(6) no . 8_544 C5 S1 3.567(6) no . 8_545 C5 C6 3.430(8) no . 8_544 C5 C6 3.426(8) no . 8_545 C6 C5 3.426(8) no . 8_544 C6 C5 3.430(8) no . 8_545 C6 C6 3.521(8) no . 8_544 C6 C6 3.521(8) no . 8_545 C7 C7 3.399(8) no . 6_664 C7 C7 3.399(8) no . 6_665 S1 H1 2.9653 no . . S1 H4 3.2908 no . 3_765 C1 H3 3.2634 no . . C2 H4 3.2381 no . . C3 H1 3.2755 no . . C4 H2 3.2249 no . . C5 H1 3.2869 no . . C5 H3 3.2300 no . . C6 H2 3.2030 no . . C6 H4 3.2733 no . . C7 H4 2.8094 no . 3_765 H1 H2 2.3300 no . . H2 H3 2.2974 no . . H3 H4 2.2980 no . . S1 H2 3.1114 no . 2_665 S1 H2 3.1990 no . 7_555 P1 H1 3.3890 no . . P1 H1 3.3890 no . 2_665 P1 H1 3.3890 no . 3_755 P1 H1 3.3890 no . 4_645 P1 H3 3.5496 no . 5_645 P1 H3 3.5496 no . 6_654 P1 H3 3.5496 no . 7_555 P1 H3 3.5496 no . 8_544 F1 H1 3.4495 no . . F1 H1 3.4495 no . 3_755 F1 H3 2.5691 no . 5_645 F1 H3 3.3844 no . 6_655 F1 H3 2.5691 no . 7_555 F1 H3 3.3844 no . 8_545 F1 H4 3.5090 no . 5_645 F1 H4 3.5090 no . 7_555 F2 H1 2.6027 no . . F2 H1 2.5132 no . 2_665 F2 H3 3.0698 no . 7_555 F2 H3 3.2335 no . 8_544 F2 H4 3.1981 no . 8_544 C2 H1 3.5780 no . 8_544 C2 H1 3.5321 no . 8_545 C2 H2 3.5876 no . 8_544 C2 H4 3.2138 no . 2_565 C3 H1 3.4025 no . 8_544 C3 H1 3.3519 no . 8_545 C3 H4 3.2829 no . 2_565 C4 H2 3.4144 no . 4_655 C4 H3 3.5270 no . 4_655 H1 P1 3.3890 no . . H1 F1 3.4495 no . . H1 F2 2.6027 no . . H1 F2 2.5132 no . 4_645 H1 C2 3.5321 no . 8_544 H1 C2 3.5780 no . 8_545 H1 C3 3.3519 no . 8_544 H1 C3 3.4025 no . 8_545 H1 H3 3.5003 no . 8_544 H1 H3 3.5380 no . 8_545 H1 H4 3.4745 no . 5_645 H2 S1 3.1114 no . 4_645 H2 S1 3.1990 no . 7_455 H2 C2 3.5876 no . 8_545 H2 C4 3.4144 no . 2_565 H2 H2 3.4533 no . 8_544 H2 H2 3.4533 no . 8_545 H2 H4 2.6565 no . 2_565 H2 H4 3.4942 no . 5_645 H3 P1 3.5496 no . 5_655 H3 F1 2.5691 no . 5_655 H3 F1 3.3844 no . 6_564 H3 F2 3.0698 no . 7_455 H3 F2 3.2335 no . 8_545 H3 C4 3.5270 no . 2_565 H3 H1 3.5380 no . 8_544 H3 H1 3.5003 no . 8_545 H3 H3 3.5495 no . 2_565 H3 H3 3.5495 no . 4_655 H3 H4 2.7935 no . 2_565 H4 F1 3.5090 no . 5_655 H4 F2 3.1981 no . 8_545 H4 C2 3.2138 no . 4_655 H4 C3 3.2829 no . 4_655 H4 H1 3.4745 no . 5_655 H4 H2 2.6565 no . 4_655 H4 H2 3.4942 no . 5_655 H4 H3 2.7935 no . 4_655 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 949377' ####################################################################### # # 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_(BTBT)2PF6_ #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C28 H16 F6 P S4' _chemical_formula_moiety 'C28 H16 F6 P S4' _chemical_formula_weight 625.64 _chemical_melting_point ? _chemical_absolute_configuration ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P -4 21 c' _symmetry_space_group_name_Hall 'P -4 2n' _symmetry_Int_Tables_number 114 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 +Y,-X,-Z 3 -X,-Y,+Z 4 -Y,+X,-Z 5 1/2-X,1/2+Y,1/2-Z 6 1/2-Y,1/2-X,1/2+Z 7 1/2+X,1/2-Y,1/2-Z 8 1/2+Y,1/2+X,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 13.407(5) _cell_length_b 13.407(5) _cell_length_c 6.638(6) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1193.2(13) _cell_formula_units_Z 2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 15.21 _cell_measurement_theta_max 17.36 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 634.00 _exptl_absorpt_coefficient_mu 0.533 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.887 _exptl_absorpt_correction_T_max 0.899 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 298 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 2557 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_theta_max 29.97 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measured_fraction_theta_full 0.974 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.134 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1065 _reflns_number_gt 863 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1291 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 1065 _refine_ls_number_parameters 89 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.800 _refine_diff_density_min -0.480 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 85 Friedel Pairs' _refine_ls_abs_structure_Flack 0.1(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; C C 0.0033 0.0016 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; P P 0.1023 0.0942 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 -0.04037(6) 0.65124(6) 0.89967(18) 0.0108(3) Uani 1.0 8 d . . . P1 P 0.0000 1.0000 1.0000 0.0147(5) Uani 1.0 2 d . . . F1 F -0.02999(17) 0.88365(18) 1.0002(5) 0.0237(6) Uani 1.0 8 d . . . F2 F 0.0000 1.0000 0.7586(6) 0.0283(9) Uani 1.0 4 d . . . C1 C 0.1548(3) 0.7271(3) 0.8981(7) 0.0124(7) Uani 1.0 8 d . . . C2 C 0.2572(3) 0.7081(3) 0.8977(7) 0.0133(7) Uani 1.0 8 d . . . C3 C 0.2954(3) 0.6105(3) 0.8959(7) 0.0145(7) Uani 1.0 8 d . . . C4 C 0.2313(3) 0.5299(3) 0.8951(7) 0.0132(7) Uani 1.0 8 d . . . C5 C 0.1277(3) 0.5461(3) 0.8979(7) 0.0108(7) Uani 1.0 8 d . . . C6 C 0.0908(3) 0.6457(3) 0.8986(7) 0.0106(7) Uani 1.0 8 d . . . C7 C -0.0472(3) 0.5225(3) 0.8973(7) 0.0108(7) Uani 1.0 8 d . . . H1 H 0.1303 0.7920 0.8979 0.0149 Uiso 1.0 8 calc R . . H2 H 0.3014 0.7615 0.8988 0.0160 Uiso 1.0 8 calc R . . H3 H 0.3640 0.6002 0.8952 0.0174 Uiso 1.0 8 calc R . . H4 H 0.2565 0.4653 0.8928 0.0159 Uiso 1.0 8 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0106(4) 0.0105(5) 0.0114(4) 0.0009(3) -0.0004(5) -0.0003(5) P1 0.0120(6) 0.0120(6) 0.0200(11) 0.0000 0.0000 0.0000 F1 0.0194(13) 0.0114(11) 0.0403(16) -0.0020(10) 0.0051(12) 0.0013(12) F2 0.028(3) 0.037(3) 0.0202(18) -0.013(2) 0.0000 0.0000 C1 0.0146(17) 0.0116(16) 0.0111(17) -0.0004(13) 0.0000(18) -0.0019(15) C2 0.0128(17) 0.0140(17) 0.0133(16) -0.0029(13) -0.0012(18) -0.0024(17) C3 0.0123(17) 0.0204(19) 0.0109(16) 0.0035(14) 0.0018(18) 0.0004(19) C4 0.0131(16) 0.0172(17) 0.0094(14) 0.0019(13) 0.0023(16) -0.0019(18) C5 0.0106(15) 0.0143(16) 0.0076(15) -0.0001(13) 0.0005(16) 0.0010(18) C6 0.0135(16) 0.0108(16) 0.0076(15) 0.0005(12) -0.0013(16) -0.0028(17) C7 0.0155(17) 0.0099(16) 0.0071(16) -0.0003(13) 0.0017(15) 0.0017(15) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction WinAFC _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 C6 1.760(4) yes . . S1 C7 1.728(4) yes . . P1 F1 1.611(3) yes . . P1 F1 1.611(3) yes . 2_467 P1 F1 1.611(3) yes . 3_575 P1 F1 1.611(3) yes . 4_667 P1 F2 1.602(5) yes . . P1 F2 1.602(5) yes . 2_467 C1 C2 1.397(6) yes . . C1 C6 1.389(5) yes . . C2 C3 1.405(6) yes . . C3 C4 1.381(6) yes . . C4 C5 1.405(5) yes . . C5 C6 1.424(5) yes . . C5 C7 1.419(5) yes . 3_565 C7 C7 1.403(5) yes . 3_565 C1 H1 0.930 no . . C2 H2 0.930 no . . C3 H3 0.930 no . . C4 H4 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C6 S1 C7 90.62(17) yes . . . F1 P1 F1 90.00(12) yes . . 2_467 F1 P1 F1 179.92(14) yes . . 3_575 F1 P1 F1 90.00(12) yes . . 4_667 F1 P1 F2 90.04(10) yes . . . F1 P1 F2 89.96(10) yes . . 2_467 F1 P1 F1 90.00(12) yes 2_467 . 3_575 F1 P1 F1 179.92(14) yes 2_467 . 4_667 F1 P1 F2 89.96(10) yes 2_467 . . F1 P1 F2 90.04(10) yes 2_467 . 2_467 F1 P1 F1 90.00(12) yes 3_575 . 4_667 F1 P1 F2 90.04(10) yes 3_575 . . F1 P1 F2 89.96(10) yes 3_575 . 2_467 F1 P1 F2 89.96(10) yes 4_667 . . F1 P1 F2 90.04(10) yes 4_667 . 2_467 F2 P1 F2 180.000 yes . . 2_467 C2 C1 C6 117.6(4) yes . . . C1 C2 C3 121.9(4) yes . . . C2 C3 C4 120.1(4) yes . . . C3 C4 C5 119.6(4) yes . . . C4 C5 C6 119.3(4) yes . . . C4 C5 C7 130.7(4) yes . . 3_565 C6 C5 C7 110.1(3) yes . . 3_565 S1 C6 C1 125.8(3) yes . . . S1 C6 C5 112.8(3) yes . . . C1 C6 C5 121.5(4) yes . . . S1 C7 C5 133.5(3) yes . . 3_565 S1 C7 C7 112.5(3) yes . . 3_565 C5 C7 C7 114.0(3) yes 3_565 . 3_565 C2 C1 H1 121.189 no . . . C6 C1 H1 121.177 no . . . C1 C2 H2 119.041 no . . . C3 C2 H2 119.046 no . . . C2 C3 H3 119.947 no . . . C4 C3 H3 119.939 no . . . C3 C4 H4 120.189 no . . . C5 C4 H4 120.195 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C6 S1 C7 C5 179.5(4) no . . . 3_565 C6 S1 C7 C7 0.4(3) no . . . 3_565 C7 S1 C6 C1 179.4(4) no . . . . C7 S1 C6 C5 -0.4(3) no . . . . C2 C1 C6 S1 179.9(4) no . . . . C2 C1 C6 C5 -0.3(7) no . . . . C6 C1 C2 C3 0.7(7) no . . . . C1 C2 C3 C4 -0.2(7) no . . . . C2 C3 C4 C5 -0.5(7) no . . . . C3 C4 C5 C6 0.8(7) no . . . . C3 C4 C5 C7 179.8(5) no . . . 3_565 C4 C5 C6 S1 179.4(4) no . . . . C4 C5 C6 C1 -0.4(7) no . . . . C4 C5 C7 S1 2.0(8) no . . 3_565 3_565 C4 C5 C7 C7 -179.0(5) no . . 3_565 . C6 C5 C7 S1 -179.0(4) no . . 3_565 3_565 C6 C5 C7 C7 0.1(6) no . . 3_565 . C7 C5 C6 S1 0.2(5) no 3_565 . . . C7 C5 C6 C1 -179.6(4) no 3_565 . . . S1 C7 C7 S1 178.9(3) no . . 3_565 3_565 S1 C7 C7 C5 -0.4(5) no . . 3_565 . C5 C7 C7 S1 -0.4(5) no 3_565 . 3_565 3_565 C5 C7 C7 C5 -179.7(4) no 3_565 . 3_565 . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 S1 C4 3.529(4) no . 3_565 C1 C4 2.836(6) no . . C2 C5 2.780(6) no . . C3 C6 2.784(5) no . . S1 F1 3.190(3) no . . S1 C4 3.586(6) no . 8_455 S1 C5 3.541(6) no . 8_454 S1 C5 3.519(6) no . 8_455 S1 C7 3.593(5) no . 6_555 F1 S1 3.190(3) no . . F1 C1 3.317(5) no . . F1 C1 3.365(5) no . 2_467 F1 C3 3.521(6) no . 7_466 F1 C3 3.442(6) no . 8_455 F1 C4 3.419(6) no . 8_455 F2 F2 3.433(7) no . 2_466 F2 C3 3.282(4) no . 5_556 F2 C3 3.282(4) no . 7_466 C1 F1 3.317(5) no . . C1 F1 3.365(5) no . 4_667 C1 C1 3.591(7) no . 8_454 C1 C1 3.591(7) no . 8_455 C1 C2 3.421(7) no . 8_454 C1 C2 3.417(7) no . 8_455 C1 C3 3.507(7) no . 8_454 C1 C3 3.480(7) no . 8_455 C2 C1 3.417(7) no . 8_454 C2 C1 3.421(7) no . 8_455 C2 C2 3.447(7) no . 8_454 C2 C2 3.447(7) no . 8_455 C3 F1 3.521(6) no . 7_566 C3 F1 3.442(6) no . 8_454 C3 F2 3.282(4) no . 5_546 C3 C1 3.480(7) no . 8_454 C3 C1 3.507(7) no . 8_455 C4 S1 3.586(6) no . 8_454 C4 F1 3.419(6) no . 8_454 C4 C6 3.584(7) no . 8_454 C5 S1 3.519(6) no . 8_454 C5 S1 3.541(6) no . 8_455 C5 C6 3.376(7) no . 8_454 C5 C6 3.386(7) no . 8_455 C6 C4 3.584(7) no . 8_455 C6 C5 3.386(7) no . 8_454 C6 C5 3.376(7) no . 8_455 C6 C6 3.478(7) no . 8_454 C6 C6 3.478(7) no . 8_455 C7 S1 3.593(5) no . 6_554 C7 C7 3.352(7) no . 6_554 C7 C7 3.352(7) no . 6_555 C7 C7 3.573(7) no . 8_454 C7 C7 3.573(7) no . 8_455 S1 H1 2.9669 no . . S1 H4 3.2924 no . 3_565 C1 H3 3.2810 no . . C2 H4 3.2548 no . . C3 H1 3.2897 no . . C4 H2 3.2444 no . . C5 H1 3.2971 no . . C5 H3 3.2495 no . . C6 H2 3.2233 no . . C6 H4 3.2842 no . . C7 H4 2.8107 no . 3_565 H1 H2 2.3301 no . . H2 H3 2.3205 no . . H3 H4 2.3124 no . . S1 H2 3.0410 no . 2_467 S1 H2 3.1290 no . 7_466 S1 H4 3.5653 no . 8_455 P1 H1 3.3596 no . . P1 H1 3.3596 no . 2_467 P1 H1 3.3596 no . 3_575 P1 H1 3.3596 no . 4_667 P1 H3 3.4656 no . 5_556 P1 H3 3.4656 no . 6_565 P1 H3 3.4656 no . 7_466 P1 H3 3.4656 no . 8_455 F1 H1 2.5671 no . . F1 H1 2.4872 no . 2_467 F1 H3 2.9925 no . 7_466 F1 H3 3.1607 no . 8_455 F1 H4 3.1149 no . 8_455 F2 H1 3.4181 no . . F2 H1 3.4181 no . 3_575 F2 H3 2.4841 no . 5_556 F2 H3 3.3087 no . 6_564 F2 H3 2.4841 no . 7_466 F2 H3 3.3087 no . 8_454 F2 H4 3.4476 no . 5_556 F2 H4 3.4476 no . 7_466 C2 H1 3.5087 no . 8_454 C2 H1 3.5111 no . 8_455 C2 H2 3.5413 no . 8_454 C2 H2 3.5539 no . 8_455 C2 H4 3.1533 no . 2_567 C3 H1 3.3165 no . 8_454 C3 H1 3.3433 no . 8_455 C3 H4 3.2152 no . 2_567 C4 H2 3.3568 no . 4_657 C4 H3 3.4631 no . 4_657 H1 P1 3.3596 no . . H1 F1 2.5671 no . . H1 F1 2.4872 no . 4_667 H1 F2 3.4181 no . . H1 C2 3.5111 no . 8_454 H1 C2 3.5087 no . 8_455 H1 C3 3.3433 no . 8_454 H1 C3 3.3165 no . 8_455 H1 H3 3.4972 no . 8_454 H1 H3 3.4627 no . 8_455 H1 H4 3.3799 no . 5_556 H2 S1 3.0410 no . 4_667 H2 S1 3.1290 no . 7_566 H2 C2 3.5539 no . 8_454 H2 C2 3.5413 no . 8_455 H2 C4 3.3568 no . 2_567 H2 H2 3.4041 no . 8_454 H2 H2 3.4041 no . 8_455 H2 H4 2.6079 no . 2_567 H2 H4 3.4371 no . 5_556 H3 P1 3.4656 no . 5_546 H3 F1 2.9925 no . 7_566 H3 F1 3.1607 no . 8_454 H3 F2 2.4841 no . 5_546 H3 F2 3.3087 no . 6_655 H3 C4 3.4631 no . 2_567 H3 H1 3.4627 no . 8_454 H3 H1 3.4972 no . 8_455 H3 H3 3.4918 no . 2_567 H3 H3 3.4918 no . 4_657 H3 H4 2.7422 no . 2_567 H4 S1 3.5653 no . 8_454 H4 F1 3.1149 no . 8_454 H4 F2 3.4476 no . 5_546 H4 C2 3.1533 no . 4_657 H4 C3 3.2152 no . 4_657 H4 H1 3.3799 no . 5_546 H4 H2 2.6079 no . 4_657 H4 H2 3.4371 no . 5_546 H4 H3 2.7422 no . 4_657 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 949378'