# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 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_4a _database_code_depnum_ccdc_archive 'CCDC 916377' #TrackingRef '4a.cif' _chemical_formula_sum 'C11 H12 F6 O2' _chemical_formula_moiety 'C11 H12 F6 O2' _chemical_formula_weight 290.20 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2+Z 3 1/2+X,1/2-Y,+Z 4 -X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 9.4508(11) _cell_length_b 26.424(3) _cell_length_c 5.0500(6) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1261.1(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11417 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 68.09 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592.00 _exptl_absorpt_coefficient_mu 1.459 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku Saturn70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 29.257 _diffrn_reflns_number 14894 _diffrn_reflns_av_R_equivalents 0.0881 _diffrn_reflns_theta_max 68.13 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.980 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # 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 2197 _reflns_number_gt 2122 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1206 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2197 _refine_ls_number_parameters 172 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.6180P] 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 0.230 _refine_diff_density_min -0.230 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 938 Friedel Pairs' _refine_ls_abs_structure_Flack -0.0(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; 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) ; F F 0.0727 0.0534 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; 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 F1 F 0.2781(2) 0.19204(6) 0.9186(5) 0.0616(6) Uani 1.0 4 d . . . F2 F 0.25016(19) 0.14992(7) 0.5548(5) 0.0621(6) Uani 1.0 4 d . . . F3 F 0.6652(2) 0.03857(7) 0.9417(5) 0.0669(6) Uani 1.0 4 d . . . F4 F 0.5850(3) 0.06184(8) 0.5536(5) 0.0711(6) Uani 1.0 4 d . . . F5 F 0.6752(3) 0.13413(8) 1.1070(4) 0.0615(6) Uani 1.0 4 d . . . F6 F 0.79954(18) 0.11659(9) 0.7580(5) 0.0743(7) Uani 1.0 4 d . . . O1 O 0.43088(18) 0.22168(7) 0.5149(5) 0.0446(5) Uani 1.0 4 d . . . O3 O 0.20841(19) 0.10168(7) 1.0168(5) 0.0475(6) Uani 1.0 4 d . . . C1 C 0.4734(3) 0.18099(9) 0.6541(6) 0.0365(6) Uani 1.0 4 d . . . C2 C 0.3404(3) 0.15656(10) 0.7643(6) 0.0385(6) Uani 1.0 4 d . . . C3 C 0.3395(3) 0.10689(9) 0.9150(6) 0.0385(6) Uani 1.0 4 d . . . C4 C 0.4415(3) 0.07246(10) 0.9317(7) 0.0472(7) Uani 1.0 4 d . . . C5 C 0.5856(4) 0.07508(12) 0.8177(7) 0.0518(8) Uani 1.0 4 d . . . C6 C 0.6646(4) 0.12429(12) 0.8432(7) 0.0479(7) Uani 1.0 4 d . . . C7 C 0.6077(3) 0.16857(11) 0.6957(7) 0.0448(7) Uani 1.0 4 d . . . C8 C 0.5364(3) 0.25196(10) 0.3839(7) 0.0460(7) Uani 1.0 4 d . . . C9 C 0.4599(4) 0.29258(11) 0.2341(8) 0.0574(9) Uani 1.0 4 d . . . C10 C 0.1783(4) 0.05660(11) 1.1655(8) 0.0527(8) Uani 1.0 4 d . . . C11 C 0.0303(4) 0.06115(13) 1.2686(10) 0.0714(12) Uani 1.0 4 d . . . H4 H 0.4194 0.0427 1.0283 0.0566 Uiso 1.0 4 calc R . . H7 H 0.6762 0.1908 0.6219 0.0538 Uiso 1.0 4 calc R . . H8A H 0.5927 0.2308 0.2610 0.0552 Uiso 1.0 4 calc R . . H8B H 0.6013 0.2672 0.5155 0.0552 Uiso 1.0 4 calc R . . H9A H 0.5287 0.3137 0.1396 0.0688 Uiso 1.0 4 calc R . . H9B H 0.4061 0.3136 0.3582 0.0688 Uiso 1.0 4 calc R . . H9C H 0.3950 0.2770 0.1065 0.0688 Uiso 1.0 4 calc R . . H10A H 0.2458 0.0531 1.3143 0.0632 Uiso 1.0 4 calc R . . H10B H 0.1869 0.0264 1.0506 0.0632 Uiso 1.0 4 calc R . . H11A H -0.0356 0.0643 1.1196 0.0857 Uiso 1.0 4 calc R . . H11B H 0.0230 0.0912 1.3816 0.0857 Uiso 1.0 4 calc R . . H11C H 0.0066 0.0309 1.3720 0.0857 Uiso 1.0 4 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 F1 0.0658(11) 0.0335(8) 0.0856(14) 0.0062(8) 0.0384(11) 0.0043(9) F2 0.0506(9) 0.0635(11) 0.0723(13) -0.0169(8) -0.0242(10) 0.0273(10) F3 0.0589(10) 0.0510(10) 0.0907(15) 0.0272(8) 0.0038(11) 0.0116(11) F4 0.1023(16) 0.0588(12) 0.0523(11) 0.0091(12) 0.0104(12) -0.0172(10) F5 0.0664(13) 0.0715(12) 0.0465(11) -0.0077(10) -0.0110(9) -0.0013(10) F6 0.0386(10) 0.0871(15) 0.0972(17) 0.0216(9) 0.0163(11) 0.0293(14) O1 0.0357(9) 0.0372(9) 0.0610(13) -0.0006(8) 0.0050(10) 0.0115(9) O3 0.0369(10) 0.0379(10) 0.0678(14) -0.0013(8) 0.0015(10) 0.0151(10) C1 0.0381(13) 0.0335(12) 0.0378(14) -0.0007(11) -0.0001(11) -0.0035(12) C2 0.0335(13) 0.0349(13) 0.0471(16) 0.0020(10) -0.0012(12) 0.0004(12) C3 0.0376(13) 0.0306(12) 0.0473(16) -0.0007(10) -0.0045(12) 0.0013(12) C4 0.0462(15) 0.0349(13) 0.0605(19) 0.0012(12) -0.0023(14) 0.0060(14) C5 0.0543(19) 0.0451(16) 0.056(2) 0.0182(14) -0.0001(15) -0.0023(15) C6 0.0351(14) 0.0597(18) 0.0491(17) 0.0080(13) 0.0041(13) 0.0027(15) C7 0.0373(13) 0.0472(15) 0.0499(17) 0.0003(12) 0.0048(13) 0.0022(14) C8 0.0393(14) 0.0409(14) 0.0578(18) -0.0049(11) 0.0116(14) 0.0016(14) C9 0.0525(18) 0.0399(15) 0.080(3) -0.0008(13) 0.0187(17) 0.0147(16) C10 0.0479(16) 0.0371(15) 0.073(3) -0.0060(12) -0.0015(16) 0.0168(15) C11 0.0547(19) 0.0524(19) 0.107(4) -0.0072(15) 0.015(3) 0.028(3) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r2' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r2' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _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 F1 C2 1.354(4) yes . . F2 C2 1.370(4) yes . . F3 C5 1.374(4) yes . . F4 C5 1.379(5) yes . . F5 C6 1.361(4) yes . . F6 C6 1.361(4) yes . . O1 C1 1.346(4) yes . . O1 C8 1.440(4) yes . . O3 C3 1.349(4) yes . . O3 C10 1.437(4) yes . . C1 C2 1.519(4) yes . . C1 C7 1.328(4) yes . . C2 C3 1.517(4) yes . . C3 C4 1.328(4) yes . . C4 C5 1.480(5) yes . . C5 C6 1.505(5) yes . . C6 C7 1.488(5) yes . . C8 C9 1.499(5) yes . . C10 C11 1.497(5) yes . . C4 H4 0.950 no . . C7 H7 0.950 no . . C8 H8A 0.990 no . . C8 H8B 0.990 no . . C9 H9A 0.980 no . . C9 H9B 0.980 no . . C9 H9C 0.980 no . . C10 H10A 0.990 no . . C10 H10B 0.990 no . . C11 H11A 0.980 no . . C11 H11B 0.980 no . . C11 H11C 0.980 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 C1 O1 C8 118.5(2) yes . . . C3 O3 C10 117.8(2) yes . . . O1 C1 C2 106.5(2) yes . . . O1 C1 C7 124.5(3) yes . . . C2 C1 C7 128.9(3) yes . . . F1 C2 F2 105.2(2) yes . . . F1 C2 C1 106.1(2) yes . . . F1 C2 C3 107.9(3) yes . . . F2 C2 C1 106.7(3) yes . . . F2 C2 C3 105.8(3) yes . . . C1 C2 C3 123.8(3) yes . . . O3 C3 C2 106.6(2) yes . . . O3 C3 C4 124.9(3) yes . . . C2 C3 C4 128.3(3) yes . . . C3 C4 C5 127.7(3) yes . . . F3 C5 F4 105.4(3) yes . . . F3 C5 C4 107.1(3) yes . . . F3 C5 C6 107.2(3) yes . . . F4 C5 C4 111.1(3) yes . . . F4 C5 C6 107.7(3) yes . . . C4 C5 C6 117.6(3) yes . . . F5 C6 F6 105.6(3) yes . . . F5 C6 C5 106.5(3) yes . . . F5 C6 C7 111.5(3) yes . . . F6 C6 C5 108.0(3) yes . . . F6 C6 C7 107.4(3) yes . . . C5 C6 C7 117.2(3) yes . . . C1 C7 C6 128.3(3) yes . . . O1 C8 C9 107.2(3) yes . . . O3 C10 C11 107.5(3) yes . . . C3 C4 H4 116.161 no . . . C5 C4 H4 116.180 no . . . C1 C7 H7 115.853 no . . . C6 C7 H7 115.870 no . . . O1 C8 H8A 110.276 no . . . O1 C8 H8B 110.278 no . . . C9 C8 H8A 110.272 no . . . C9 C8 H8B 110.285 no . . . H8A C8 H8B 108.538 no . . . C8 C9 H9A 109.467 no . . . C8 C9 H9B 109.474 no . . . C8 C9 H9C 109.484 no . . . H9A C9 H9B 109.460 no . . . H9A C9 H9C 109.465 no . . . H9B C9 H9C 109.477 no . . . O3 C10 H10A 110.227 no . . . O3 C10 H10B 110.219 no . . . C11 C10 H10A 110.219 no . . . C11 C10 H10B 110.211 no . . . H10A C10 H10B 108.492 no . . . C10 C11 H11A 109.474 no . . . C10 C11 H11B 109.470 no . . . C10 C11 H11C 109.478 no . . . H11A C11 H11B 109.471 no . . . H11A C11 H11C 109.466 no . . . H11B C11 H11C 109.468 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 C1 O1 C8 C9 177.1(2) no . . . . C8 O1 C1 C2 -179.2(2) no . . . . C8 O1 C1 C7 5.1(4) no . . . . C3 O3 C10 C11 177.0(3) no . . . . C10 O3 C3 C2 178.6(3) no . . . . C10 O3 C3 C4 3.1(4) no . . . . O1 C1 C2 F1 -60.0(3) no . . . . O1 C1 C2 F2 51.8(3) no . . . . O1 C1 C2 C3 174.7(3) no . . . . O1 C1 C7 C6 -179.2(3) no . . . . C2 C1 C7 C6 6.1(5) no . . . . C7 C1 C2 F1 115.5(3) no . . . . C7 C1 C2 F2 -132.7(3) no . . . . C7 C1 C2 C3 -9.8(5) no . . . . F1 C2 C3 O3 45.8(3) no . . . . F1 C2 C3 C4 -138.9(3) no . . . . F2 C2 C3 O3 -66.5(3) no . . . . F2 C2 C3 C4 108.9(3) no . . . . C1 C2 C3 O3 170.3(3) no . . . . C1 C2 C3 C4 -14.4(5) no . . . . O3 C3 C4 C5 177.9(3) no . . . . C2 C3 C4 C5 3.4(6) no . . . . C3 C4 C5 F3 164.1(3) no . . . . C3 C4 C5 F4 -81.3(4) no . . . . C3 C4 C5 C6 43.4(5) no . . . . F3 C5 C6 F5 -61.6(3) no . . . . F3 C5 C6 F6 51.5(4) no . . . . F3 C5 C6 C7 172.9(3) no . . . . F4 C5 C6 F5 -174.5(3) no . . . . F4 C5 C6 F6 -61.4(3) no . . . . F4 C5 C6 C7 59.9(4) no . . . . C4 C5 C6 F5 59.0(4) no . . . . C4 C5 C6 F6 172.1(3) no . . . . C4 C5 C6 C7 -66.6(4) no . . . . F5 C6 C7 C1 -86.1(4) no . . . . F6 C6 C7 C1 158.6(3) no . . . . C5 C6 C7 C1 37.0(5) no . . . . 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 F1 O1 2.618(3) no . . F1 O3 2.526(3) no . . F1 C4 3.518(4) no . . F1 C7 3.370(4) no . . F2 O1 2.560(3) no . . F2 O3 2.688(4) no . . F2 C4 3.329(4) no . . F2 C7 3.488(4) no . . F3 F5 2.661(3) no . . F3 F6 2.593(3) no . . F3 C3 3.571(4) no . . F4 F5 3.491(3) no . . F4 F6 2.696(3) no . . F4 C1 3.359(4) no . . F4 C2 3.569(4) no . . F4 C3 3.183(4) no . . F4 C7 2.918(4) no . . F5 C1 3.225(4) no . . F5 C3 3.394(4) no . . F5 C4 2.883(4) no . . F6 C1 3.560(4) no . . C1 C4 3.206(4) no . . C1 C5 3.105(4) no . . C2 C5 3.174(5) no . . C2 C6 3.205(4) no . . C3 C6 3.128(4) no . . C3 C7 3.211(4) no . . C4 C7 3.215(4) no . . C4 C10 2.786(5) no . . C7 C8 2.791(5) no . . F1 F2 3.410(3) no . 1_556 F1 O1 3.430(3) no . 1_556 F1 C8 3.596(4) no . 3_456 F1 C9 3.542(4) no . 1_556 F1 C9 3.427(4) no . 3_456 F2 F1 3.410(3) no . 1_554 F2 O3 3.027(4) no . 1_554 F2 C3 3.528(4) no . 1_554 F2 C8 3.398(4) no . 3_455 F2 C9 3.529(4) no . 3_455 F2 C10 3.226(4) no . 1_554 F2 C11 3.451(5) no . 1_554 F3 F4 3.240(4) no . 1_556 F3 F4 3.598(3) no . 4_655 F3 C10 3.234(4) no . 4_654 F4 F3 3.240(4) no . 1_554 F4 F3 3.598(3) no . 4_654 F4 F5 3.076(3) no . 1_554 F4 C4 3.432(4) no . 1_554 F5 F4 3.076(3) no . 1_556 F5 F6 3.522(3) no . 1_556 F5 C1 3.578(4) no . 1_556 F5 C7 3.174(4) no . 1_556 F5 C9 3.377(4) no . 3_556 F6 F5 3.522(3) no . 1_554 O1 F1 3.430(3) no . 1_554 O3 F2 3.027(4) no . 1_556 C1 F5 3.578(4) no . 1_554 C3 F2 3.528(4) no . 1_556 C4 F4 3.432(4) no . 1_556 C7 F5 3.174(4) no . 1_554 C8 F1 3.596(4) no . 3_554 C8 F2 3.398(4) no . 3_555 C9 F1 3.542(4) no . 1_554 C9 F1 3.427(4) no . 3_554 C9 F2 3.529(4) no . 3_555 C9 F5 3.377(4) no . 3_454 C10 F2 3.226(4) no . 1_556 C10 F3 3.234(4) no . 4_655 C11 F2 3.451(5) no . 1_556 F3 H4 2.3658 no . . F4 H4 2.9077 no . . F4 H7 3.5318 no . . F5 H4 3.4414 no . . F5 H7 2.8710 no . . F6 H7 2.3826 no . . O1 H7 2.5164 no . . O1 H9A 3.2180 no . . O1 H9B 2.5653 no . . O1 H9C 2.5511 no . . O3 H4 2.5323 no . . O3 H11A 2.5615 no . . O3 H11B 2.5573 no . . O3 H11C 3.2170 no . . C1 H8A 2.6352 no . . C1 H8B 2.6718 no . . C2 H4 3.3756 no . . C2 H7 3.3770 no . . C3 H10A 2.6210 no . . C3 H10B 2.6594 no . . C4 H10A 2.7232 no . . C4 H10B 2.7626 no . . C5 H7 3.3258 no . . C6 H4 3.3016 no . . C7 H8A 2.7470 no . . C7 H8B 2.7609 no . . C8 H7 2.4086 no . . C10 H4 2.4101 no . . H4 H10A 2.2033 no . . H4 H10B 2.2416 no . . H7 H8A 2.2504 no . . H7 H8B 2.2054 no . . H8A H9A 2.3528 no . . H8A H9B 2.8523 no . . H8A H9C 2.3640 no . . H8B H9A 2.3633 no . . H8B H9B 2.3538 no . . H8B H9C 2.8524 no . . H10A H11A 2.8503 no . . H10A H11B 2.3580 no . . H10A H11C 2.3534 no . . H10B H11A 2.3548 no . . H10B H11B 2.8503 no . . H10B H11C 2.3565 no . . F1 H7 3.5718 no . 3_455 F1 H8A 3.5883 no . 1_556 F1 H8A 3.1962 no . 3_456 F1 H8B 2.8454 no . 3_455 F1 H9A 2.6128 no . 3_456 F1 H9C 2.6766 no . 1_556 F2 H8B 2.6107 no . 3_455 F2 H9A 3.1152 no . 3_455 F2 H9B 3.5342 no . 3_455 F2 H10A 2.8317 no . 1_554 F2 H11B 2.7898 no . 1_554 F3 H4 3.0989 no . 4_654 F3 H10A 2.6446 no . 4_654 F3 H10B 2.9672 no . 4_654 F3 H11A 3.0446 no . 1_655 F4 H4 3.1213 no . 1_554 F4 H4 2.7643 no . 4_654 F4 H10A 3.4338 no . 1_554 F4 H10B 3.1754 no . 4_654 F5 H7 3.0008 no . 1_556 F5 H8A 2.7821 no . 1_556 F5 H9B 2.8775 no . 3_556 F5 H9C 3.1352 no . 3_556 F5 H11A 3.2990 no . 1_655 F6 H9A 3.4347 no . 3_556 F6 H9B 2.9143 no . 3_555 F6 H9C 3.4369 no . 3_556 F6 H11A 2.7699 no . 1_655 F6 H11B 2.9197 no . 1_654 F6 H11C 3.5709 no . 1_654 O1 H7 3.3815 no . 3_455 O1 H8B 3.1285 no . 3_455 O1 H9C 3.3434 no . 1_556 O3 H9A 2.8762 no . 3_456 C1 H8A 3.5209 no . 1_556 C1 H9C 3.4940 no . 1_556 C2 H8B 3.2778 no . 3_455 C2 H9A 3.5906 no . 3_456 C3 H10A 3.4645 no . 1_554 C5 H4 3.4374 no . 4_654 C6 H8A 3.5831 no . 1_556 C6 H11A 3.5340 no . 1_655 C7 H8A 3.2976 no . 1_556 C7 H9B 3.3283 no . 3_555 C9 H7 3.3497 no . 3_455 C9 H8A 3.5281 no . 3_455 C9 H11B 3.2160 no . 3_554 C10 H11C 3.2559 no . 4_554 C11 H9A 3.3711 no . 3_456 C11 H9B 3.5408 no . 3_456 C11 H10B 3.4051 no . 4_555 C11 H11C 3.1707 no . 4_554 H4 F3 3.0989 no . 4_655 H4 F4 3.1213 no . 1_556 H4 F4 2.7643 no . 4_655 H4 C5 3.4374 no . 4_655 H7 F1 3.5718 no . 3_555 H7 F5 3.0008 no . 1_554 H7 O1 3.3815 no . 3_555 H7 C9 3.3497 no . 3_555 H7 H8A 3.4865 no . 1_556 H7 H9B 2.5510 no . 3_555 H7 H9C 3.4319 no . 3_555 H7 H9C 3.3148 no . 3_556 H8A F1 3.5883 no . 1_554 H8A F1 3.1962 no . 3_554 H8A F5 2.7821 no . 1_554 H8A C1 3.5209 no . 1_554 H8A C6 3.5831 no . 1_554 H8A C7 3.2976 no . 1_554 H8A C9 3.5281 no . 3_555 H8A H7 3.4865 no . 1_554 H8A H9B 3.2236 no . 3_555 H8A H9C 2.9695 no . 3_555 H8B F1 2.8454 no . 3_555 H8B F2 2.6107 no . 3_555 H8B O1 3.1285 no . 3_555 H8B C2 3.2778 no . 3_555 H8B H9A 3.4515 no . 1_556 H8B H9C 3.5739 no . 1_556 H9A F1 2.6128 no . 3_554 H9A F2 3.1152 no . 3_555 H9A F6 3.4347 no . 3_454 H9A O3 2.8762 no . 3_554 H9A C2 3.5906 no . 3_554 H9A C11 3.3711 no . 3_554 H9A H8B 3.4515 no . 1_554 H9A H11A 3.2825 no . 3_554 H9A H11B 2.7955 no . 3_554 H9B F2 3.5342 no . 3_555 H9B F5 2.8775 no . 3_454 H9B F6 2.9143 no . 3_455 H9B C7 3.3283 no . 3_455 H9B C11 3.5408 no . 3_554 H9B H7 2.5510 no . 3_455 H9B H8A 3.2236 no . 3_455 H9B H11A 3.4879 no . 3_554 H9B H11B 2.7504 no . 3_554 H9C F1 2.6766 no . 1_554 H9C F5 3.1352 no . 3_454 H9C F6 3.4369 no . 3_454 H9C O1 3.3434 no . 1_554 H9C C1 3.4940 no . 1_554 H9C H7 3.3148 no . 3_454 H9C H7 3.4319 no . 3_455 H9C H8A 2.9695 no . 3_455 H9C H8B 3.5739 no . 1_554 H10A F2 2.8317 no . 1_556 H10A F3 2.6446 no . 4_655 H10A F4 3.4338 no . 1_556 H10A C3 3.4645 no . 1_556 H10B F3 2.9672 no . 4_655 H10B F4 3.1754 no . 4_655 H10B C11 3.4051 no . 4_554 H10B H11A 3.5393 no . 4_554 H10B H11C 2.5404 no . 4_554 H11A F3 3.0446 no . 1_455 H11A F5 3.2990 no . 1_455 H11A F6 2.7699 no . 1_455 H11A C6 3.5340 no . 1_455 H11A H9A 3.2825 no . 3_456 H11A H9B 3.4879 no . 3_456 H11A H10B 3.5393 no . 4_555 H11A H11C 2.8234 no . 4_554 H11B F2 2.7898 no . 1_556 H11B F6 2.9197 no . 1_456 H11B C9 3.2160 no . 3_456 H11B H9A 2.7955 no . 3_456 H11B H9B 2.7504 no . 3_456 H11C F6 3.5709 no . 1_456 H11C C10 3.2559 no . 4_555 H11C C11 3.1707 no . 4_555 H11C H10B 2.5404 no . 4_555 H11C H11A 2.8234 no . 4_555 H11C H11C 3.0108 no . 4_554 H11C H11C 3.0108 no . 4_555 data_4b _database_code_depnum_ccdc_archive 'CCDC 916378' #TrackingRef '4b.cif' _chemical_formula_sum 'C19 H10 Br2 F6 O2' _chemical_formula_moiety 'C19 H10 Br2 F6 O2' _chemical_formula_weight 544.09 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 5.512(2) _cell_length_b 13.104(7) _cell_length_c 14.668(8) _cell_angle_alpha 115.201(10) _cell_angle_beta 90.957(10) _cell_angle_gamma 98.891(9) _cell_volume 943.0(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2851 _cell_measurement_theta_min 1.54 _cell_measurement_theta_max 25.35 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.060 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.916 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528.00 _exptl_absorpt_coefficient_mu 4.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.488 _exptl_absorpt_correction_T_max 0.916 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_reflns_number 6092 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_theta_max 25.36 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.971 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 10 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # 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 3342 _reflns_number_gt 2201 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1210 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3342 _refine_ls_number_parameters 262 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0423P)^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 0.007 _refine_diff_density_max 0.670 _refine_diff_density_min -0.650 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 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) ; Br Br -0.2901 2.4595 ; 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) ; O O 0.0106 0.0060 ; 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 Br11 Br -0.78401(11) 0.12641(5) 0.05535(5) 0.0433(3) Uani 1.0 2 d . . . Br17 Br 0.80463(13) 1.41585(6) 0.37952(6) 0.0535(3) Uani 1.0 2 d . . . F1 F -0.0420(7) 0.7569(3) 0.1043(3) 0.0478(10) Uani 1.0 2 d . . . F2 F -0.2872(6) 0.8341(3) 0.2173(3) 0.0478(10) Uani 1.0 2 d . . . F3 F 0.2589(7) 0.8975(3) 0.5122(3) 0.0497(10) Uani 1.0 2 d . . . F4 F -0.1434(6) 0.8605(4) 0.4394(3) 0.0515(11) Uani 1.0 2 d . . . F5 F 0.3510(6) 0.7156(4) 0.3718(3) 0.0603(12) Uani 1.0 2 d . . . F6 F 0.0078(7) 0.6949(3) 0.4570(3) 0.0468(10) Uani 1.0 2 d . . . O1 O -0.2765(8) 0.5978(4) 0.1261(4) 0.0504(13) Uani 1.0 2 d . . . O3 O 0.2147(8) 0.9388(4) 0.2128(3) 0.0440(11) Uani 1.0 2 d . . . C1 C -0.1396(9) 0.6755(5) 0.2122(5) 0.0262(13) Uani 1.0 2 d . . . C2 C -0.0774(10) 0.7858(5) 0.2025(5) 0.0276(14) Uani 1.0 2 d . . . C3 C 0.1366(10) 0.8790(5) 0.2655(5) 0.0260(13) Uani 1.0 2 d . . . C4 C 0.2273(11) 0.9030(6) 0.3574(5) 0.0426(17) Uani 1.0 2 d . . . C5 C 0.1315(17) 0.8455(7) 0.4198(6) 0.081(3) Uani 1.0 2 d . . . C6 C 0.0718(18) 0.7305(8) 0.3847(6) 0.085(3) Uani 1.0 2 d . . . C7 C -0.0823(11) 0.6542(5) 0.2897(5) 0.0371(15) Uani 1.0 2 d . . . C8 C -0.3808(11) 0.4890(6) 0.1174(5) 0.0353(15) Uani 1.0 2 d . . . C9 C -0.2879(12) 0.3972(6) 0.0552(5) 0.0419(16) Uani 1.0 2 d . . . C10 C -0.4033(11) 0.2888(6) 0.0380(5) 0.0396(16) Uani 1.0 2 d . . . C11 C -0.6141(10) 0.2759(5) 0.0848(5) 0.0330(15) Uani 1.0 2 d . . . C12 C -0.7053(11) 0.3692(6) 0.1491(5) 0.0452(18) Uani 1.0 2 d . . . C13 C -0.5892(12) 0.4776(6) 0.1637(6) 0.052(2) Uani 1.0 2 d . . . C14 C 0.3565(10) 1.0482(5) 0.2602(5) 0.0307(14) Uani 1.0 2 d . . . C15 C 0.2693(10) 1.1370(6) 0.3352(5) 0.0345(15) Uani 1.0 2 d . . . C16 C 0.4040(11) 1.2459(5) 0.3703(5) 0.0331(15) Uani 1.0 2 d . . . C17 C 0.6220(10) 1.2646(5) 0.3308(5) 0.0312(14) Uani 1.0 2 d . . . C18 C 0.7101(10) 1.1759(6) 0.2576(5) 0.0355(16) Uani 1.0 2 d . . . C19 C 0.5774(11) 1.0667(6) 0.2225(5) 0.0352(15) Uani 1.0 2 d . . . H4 H 0.3667 0.9627 0.3859 0.0511 Uiso 1.0 2 calc R . . H7 H -0.1493 0.5799 0.2832 0.0445 Uiso 1.0 2 calc R . . H9 H -0.1433 0.4071 0.0234 0.0502 Uiso 1.0 2 calc R . . H10 H -0.3388 0.2235 -0.0055 0.0476 Uiso 1.0 2 calc R . . H12 H -0.8460 0.3601 0.1833 0.0543 Uiso 1.0 2 calc R . . H13 H -0.6544 0.5434 0.2057 0.0623 Uiso 1.0 2 calc R . . H15 H 0.1189 1.1232 0.3622 0.0414 Uiso 1.0 2 calc R . . H16 H 0.3466 1.3084 0.4219 0.0397 Uiso 1.0 2 calc R . . H18 H 0.8617 1.1897 0.2314 0.0426 Uiso 1.0 2 calc R . . H19 H 0.6378 1.0042 0.1723 0.0423 Uiso 1.0 2 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 Br11 0.0527(4) 0.0325(5) 0.0406(5) -0.0125(3) -0.0060(4) 0.0192(4) Br17 0.0700(5) 0.0323(5) 0.0511(6) -0.0215(4) -0.0133(4) 0.0223(4) F1 0.068(3) 0.039(3) 0.022(3) -0.0244(18) -0.0082(18) 0.0114(18) F2 0.0347(19) 0.030(2) 0.076(3) 0.0002(17) -0.0112(18) 0.022(2) F3 0.072(3) 0.036(3) 0.031(3) -0.0172(19) -0.0237(19) 0.0157(19) F4 0.047(2) 0.074(3) 0.047(3) 0.030(2) 0.0218(19) 0.032(3) F5 0.041(2) 0.088(4) 0.047(3) 0.031(3) -0.0011(19) 0.019(3) F6 0.070(3) 0.042(3) 0.029(3) -0.0135(19) -0.0038(18) 0.0237(19) O1 0.068(3) 0.031(3) 0.043(3) -0.028(3) -0.032(3) 0.021(3) O3 0.067(3) 0.033(3) 0.024(3) -0.025(3) -0.010(2) 0.016(3) C1 0.024(3) 0.018(4) 0.025(4) -0.006(3) -0.004(3) 0.001(3) C2 0.034(4) 0.027(4) 0.024(4) 0.002(3) 0.003(3) 0.015(3) C3 0.029(3) 0.024(4) 0.022(4) -0.006(3) -0.001(3) 0.011(3) C4 0.044(4) 0.038(4) 0.043(5) -0.021(3) -0.015(4) 0.025(4) C5 0.137(8) 0.049(6) 0.037(5) -0.059(5) -0.048(5) 0.026(5) C6 0.146(8) 0.060(6) 0.031(5) -0.054(6) -0.027(5) 0.030(5) C7 0.054(4) 0.025(4) 0.025(4) -0.013(3) -0.009(3) 0.011(3) C8 0.039(4) 0.028(4) 0.034(4) -0.015(3) -0.021(3) 0.017(4) C9 0.052(4) 0.033(4) 0.031(4) -0.011(4) -0.004(4) 0.010(4) C10 0.043(4) 0.032(4) 0.033(4) -0.005(3) 0.000(3) 0.009(4) C11 0.033(4) 0.026(4) 0.035(4) -0.009(3) -0.011(3) 0.014(3) C12 0.040(4) 0.031(4) 0.054(5) 0.007(4) 0.007(4) 0.008(4) C13 0.051(4) 0.021(4) 0.062(6) 0.002(4) -0.008(4) 0.000(4) C14 0.043(4) 0.022(4) 0.022(4) -0.017(3) -0.013(3) 0.013(3) C15 0.034(4) 0.038(4) 0.033(4) -0.003(3) 0.001(3) 0.021(4) C16 0.048(4) 0.022(4) 0.030(4) 0.007(3) 0.007(3) 0.011(3) C17 0.037(4) 0.023(4) 0.029(4) -0.011(3) -0.010(3) 0.013(3) C18 0.030(4) 0.045(5) 0.040(5) -0.005(3) 0.002(3) 0.031(4) C19 0.044(4) 0.031(4) 0.032(4) 0.002(3) 0.001(3) 0.016(4) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_structure_solution 'DIRDIF99-PATTY (Gould, et al., 1999)' _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 Br11 C11 1.898(6) yes . . Br17 C17 1.899(6) yes . . F1 C2 1.351(7) yes . . F2 C2 1.380(7) yes . . F3 C5 1.352(9) yes . . F4 C5 1.574(11) yes . . F5 C6 1.586(11) yes . . F6 C6 1.360(11) yes . . O1 C1 1.355(6) yes . . O1 C8 1.403(9) yes . . O3 C3 1.348(9) yes . . O3 C14 1.392(7) yes . . C1 C2 1.500(10) yes . . C1 C7 1.325(11) yes . . C2 C3 1.515(7) yes . . C3 C4 1.317(10) yes . . C4 C5 1.472(13) yes . . C5 C6 1.350(12) yes . . C6 C7 1.474(9) yes . . C8 C9 1.346(9) yes . . C8 C13 1.365(10) yes . . C9 C10 1.377(10) yes . . C10 C11 1.383(9) yes . . C11 C12 1.364(9) yes . . C12 C13 1.389(10) yes . . C14 C15 1.377(8) yes . . C14 C19 1.376(9) yes . . C15 C16 1.374(8) yes . . C16 C17 1.376(9) yes . . C17 C18 1.367(8) yes . . C18 C19 1.372(9) yes . . C4 H4 0.950 no . . C7 H7 0.950 no . . C9 H9 0.950 no . . C10 H10 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 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 C1 O1 C8 120.1(6) yes . . . C3 O3 C14 121.4(5) yes . . . O1 C1 C2 107.4(6) yes . . . O1 C1 C7 124.2(6) yes . . . C2 C1 C7 128.4(5) yes . . . F1 C2 F2 104.6(5) yes . . . F1 C2 C1 106.4(5) yes . . . F1 C2 C3 107.3(5) yes . . . F2 C2 C1 107.3(5) yes . . . F2 C2 C3 107.7(5) yes . . . C1 C2 C3 122.3(6) yes . . . O3 C3 C2 107.9(6) yes . . . O3 C3 C4 124.7(5) yes . . . C2 C3 C4 127.3(7) yes . . . C3 C4 C5 125.8(6) yes . . . F3 C5 F4 105.5(6) yes . . . F3 C5 C4 109.5(6) yes . . . F3 C5 C6 113.4(9) yes . . . F4 C5 C4 110.1(8) yes . . . F4 C5 C6 91.9(7) yes . . . C4 C5 C6 123.6(7) yes . . . F5 C6 F6 104.2(7) yes . . . F5 C6 C5 92.2(7) yes . . . F5 C6 C7 110.0(6) yes . . . F6 C6 C5 114.0(7) yes . . . F6 C6 C7 108.8(7) yes . . . C5 C6 C7 124.5(10) yes . . . C1 C7 C6 128.6(7) yes . . . O1 C8 C9 119.1(6) yes . . . O1 C8 C13 118.9(6) yes . . . C9 C8 C13 121.6(7) yes . . . C8 C9 C10 119.7(7) yes . . . C9 C10 C11 119.3(6) yes . . . Br11 C11 C10 119.4(5) yes . . . Br11 C11 C12 119.7(5) yes . . . C10 C11 C12 120.8(6) yes . . . C11 C12 C13 118.9(7) yes . . . C8 C13 C12 119.5(6) yes . . . O3 C14 C15 121.4(5) yes . . . O3 C14 C19 117.2(5) yes . . . C15 C14 C19 121.1(6) yes . . . C14 C15 C16 118.8(6) yes . . . C15 C16 C17 120.0(5) yes . . . Br17 C17 C16 119.4(4) yes . . . Br17 C17 C18 119.5(5) yes . . . C16 C17 C18 121.1(6) yes . . . C17 C18 C19 119.4(6) yes . . . C14 C19 C18 119.7(6) yes . . . C3 C4 H4 117.123 no . . . C5 C4 H4 117.126 no . . . C1 C7 H7 115.689 no . . . C6 C7 H7 115.686 no . . . C8 C9 H9 120.133 no . . . C10 C9 H9 120.132 no . . . C9 C10 H10 120.336 no . . . C11 C10 H10 120.337 no . . . C11 C12 H12 120.540 no . . . C13 C12 H12 120.539 no . . . C8 C13 H13 120.243 no . . . C12 C13 H13 120.248 no . . . C14 C15 H15 120.620 no . . . C16 C15 H15 120.612 no . . . C15 C16 H16 120.021 no . . . C17 C16 H16 120.016 no . . . C17 C18 H18 120.311 no . . . C19 C18 H18 120.311 no . . . C14 C19 H19 120.159 no . . . C18 C19 H19 120.165 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 C1 O1 C8 C9 -108.7(6) no . . . . C1 O1 C8 C13 78.1(7) no . . . . C8 O1 C1 C2 -174.2(4) no . . . . C8 O1 C1 C7 4.1(8) no . . . . C3 O3 C14 C15 -60.4(9) no . . . . C3 O3 C14 C19 125.6(6) no . . . . C14 O3 C3 C2 160.8(5) no . . . . C14 O3 C3 C4 -16.3(8) no . . . . O1 C1 C2 F1 -35.9(6) no . . . . O1 C1 C2 F2 75.5(5) no . . . . O1 C1 C2 C3 -159.5(4) no . . . . O1 C1 C7 C6 177.6(5) no . . . . C2 C1 C7 C6 -4.5(10) no . . . . C7 C1 C2 F1 145.8(6) no . . . . C7 C1 C2 F2 -102.7(7) no . . . . C7 C1 C2 C3 22.3(9) no . . . . F1 C2 C3 O3 29.7(6) no . . . . F1 C2 C3 C4 -153.2(5) no . . . . F2 C2 C3 O3 -82.4(6) no . . . . F2 C2 C3 C4 94.7(7) no . . . . C1 C2 C3 O3 152.8(5) no . . . . C1 C2 C3 C4 -30.1(8) no . . . . O3 C3 C4 C5 174.4(5) no . . . . C2 C3 C4 C5 -2.3(10) no . . . . C3 C4 C5 F3 -175.8(6) no . . . . C3 C4 C5 F4 -60.2(8) no . . . . C3 C4 C5 C6 46.4(12) no . . . . F3 C5 C6 F5 -68.6(8) no . . . . F3 C5 C6 F6 38.0(11) no . . . . F3 C5 C6 C7 175.2(7) no . . . . F4 C5 C6 F5 -176.4(5) no . . . . F4 C5 C6 F6 -69.8(8) no . . . . F4 C5 C6 C7 67.4(9) no . . . . C4 C5 C6 F5 67.8(10) no . . . . C4 C5 C6 F6 174.4(8) no . . . . C4 C5 C6 C7 -48.3(14) no . . . . F5 C6 C7 C1 -89.9(9) no . . . . F6 C6 C7 C1 156.5(6) no . . . . C5 C6 C7 C1 17.5(13) no . . . . O1 C8 C9 C10 -173.5(6) no . . . . O1 C8 C13 C12 174.9(6) no . . . . C9 C8 C13 C12 1.9(11) no . . . . C13 C8 C9 C10 -0.5(11) no . . . . C8 C9 C10 C11 0.2(11) no . . . . C9 C10 C11 Br11 176.5(6) no . . . . C9 C10 C11 C12 -1.4(10) no . . . . Br11 C11 C12 C13 -175.1(5) no . . . . C10 C11 C12 C13 2.8(11) no . . . . C11 C12 C13 C8 -3.0(11) no . . . . O3 C14 C15 C16 -172.0(6) no . . . . O3 C14 C19 C18 171.9(6) no . . . . C15 C14 C19 C18 -2.1(11) no . . . . C19 C14 C15 C16 1.8(11) no . . . . C14 C15 C16 C17 -0.2(11) no . . . . C15 C16 C17 Br17 179.6(6) no . . . . C15 C16 C17 C18 -1.0(11) no . . . . Br17 C17 C18 C19 -179.9(5) no . . . . C16 C17 C18 C19 0.6(11) no . . . . C17 C18 C19 C14 0.9(11) no . . . . 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 F1 O1 2.422(7) no . . F1 O3 2.422(5) no . . F1 C4 3.541(7) no . . F1 C7 3.507(9) no . . F2 F4 3.200(6) no . . F2 O1 2.813(6) no . . F2 O3 2.906(6) no . . F2 C4 3.243(7) no . . F2 C7 3.299(9) no . . F3 F5 2.532(5) no . . F3 F6 2.572(5) no . . F3 C3 3.569(8) no . . F4 F5 3.479(6) no . . F4 F6 2.549(7) no . . F4 C1 3.182(6) no . . F4 C2 3.228(8) no . . F4 C3 3.081(8) no . . F4 C7 2.737(7) no . . F5 C1 3.372(7) no . . F5 C3 3.461(9) no . . F5 C4 2.738(10) no . . F6 C1 3.561(8) no . . C1 C4 3.178(7) no . . C1 C5 3.084(9) no . . C1 C9 3.337(8) no . . C1 C13 3.123(8) no . . C2 C5 3.094(11) no . . C2 C6 3.178(13) no . . C3 C6 3.111(13) no . . C3 C7 3.173(10) no . . C3 C15 3.046(9) no . . C3 C19 3.446(9) no . . C4 C7 3.161(9) no . . C4 C14 2.844(11) no . . C4 C15 3.193(11) no . . C7 C8 2.808(8) no . . C7 C13 3.281(8) no . . C8 C11 2.722(9) no . . C9 C12 2.756(10) no . . C10 C13 2.745(9) no . . C14 C17 2.724(8) no . . C15 C18 2.767(9) no . . C16 C19 2.750(8) no . . Br11 Br11 3.4832(15) no . 2_355 Br11 F1 3.488(5) no . 2_465 Br11 C19 3.541(8) no . 1_445 Br17 F6 3.327(4) no . 1_665 Br17 F6 3.502(5) no . 2_676 F1 Br11 3.488(5) no . 2_465 F1 C9 3.180(7) no . 2_565 F1 C10 3.495(8) no . 2_465 F1 C10 3.210(8) no . 2_565 F1 C11 3.166(8) no . 2_465 F1 C12 3.517(8) no . 2_465 F2 O3 3.264(6) no . 1_455 F2 C3 3.351(7) no . 1_455 F2 C4 3.399(7) no . 1_455 F2 C14 3.516(8) no . 1_455 F2 C19 3.218(9) no . 1_455 F3 F4 3.521(6) no . 1_655 F3 F4 3.113(7) no . 2_576 F3 C4 3.433(6) no . 2_676 F4 F3 3.521(6) no . 1_455 F4 F3 3.113(7) no . 2_576 F4 F4 3.408(6) no . 2_576 F4 F5 3.004(5) no . 1_455 F4 C4 3.365(7) no . 2_576 F4 C5 3.501(9) no . 2_576 F4 C15 3.377(9) no . 2_576 F5 F4 3.004(5) no . 1_655 F5 C7 3.454(7) no . 1_655 F5 C13 3.375(7) no . 1_655 F6 Br17 3.327(4) no . 1_445 F6 Br17 3.502(5) no . 2_676 F6 C15 3.457(7) no . 2_576 F6 C16 3.351(7) no . 2_576 F6 C17 3.490(8) no . 2_676 O1 C9 3.582(9) no . 2_465 O3 F2 3.264(6) no . 1_655 C3 F2 3.351(7) no . 1_655 C4 F2 3.399(7) no . 1_655 C4 F3 3.433(6) no . 2_676 C4 F4 3.365(7) no . 2_576 C5 F4 3.501(9) no . 2_576 C7 F5 3.454(7) no . 1_455 C9 F1 3.180(7) no . 2_565 C9 O1 3.582(9) no . 2_465 C10 F1 3.495(8) no . 2_465 C10 F1 3.210(8) no . 2_565 C11 F1 3.166(8) no . 2_465 C12 F1 3.517(8) no . 2_465 C13 F5 3.375(7) no . 1_455 C14 F2 3.516(8) no . 1_655 C15 F4 3.377(9) no . 2_576 C15 F6 3.457(7) no . 2_576 C15 C18 3.452(9) no . 1_455 C16 F6 3.351(7) no . 2_576 C17 F6 3.490(8) no . 2_676 C18 C15 3.452(9) no . 1_655 C19 Br11 3.541(8) no . 1_665 C19 F2 3.218(9) no . 1_655 Br11 H10 2.9177 no . . Br11 H12 2.9102 no . . Br17 H16 2.9052 no . . Br17 H18 2.9039 no . . F3 H4 2.3970 no . . F4 H4 3.1813 no . . F4 H7 3.3993 no . . F5 H4 3.1429 no . . F5 H7 2.9751 no . . F6 H7 2.4023 no . . O1 H7 2.5130 no . . O1 H9 2.5398 no . . O1 H13 2.5567 no . . O3 H4 2.5335 no . . O3 H15 2.6162 no . . O3 H19 2.5278 no . . C1 H9 3.4234 no . . C1 H13 3.0636 no . . C2 H4 3.3642 no . . C2 H7 3.3527 no . . C3 H15 2.9150 no . . C3 H19 3.5809 no . . C4 H15 3.0082 no . . C5 H7 3.2885 no . . C6 H4 3.2131 no . . C7 H13 3.2406 no . . C8 H7 2.4337 no . . C8 H10 3.2133 no . . C8 H12 3.2398 no . . C9 H7 3.1670 no . . C9 H13 3.2198 no . . C10 H12 3.2483 no . . C11 H9 3.2431 no . . C11 H13 3.2316 no . . C12 H10 3.2446 no . . C13 H7 2.7567 no . . C13 H9 3.2220 no . . C14 H4 2.5373 no . . C14 H16 3.2292 no . . C14 H18 3.2369 no . . C15 H4 2.8057 no . . C15 H19 3.2523 no . . C16 H18 3.2447 no . . C17 H15 3.2427 no . . C17 H19 3.2247 no . . C18 H16 3.2414 no . . C19 H4 3.3678 no . . C19 H15 3.2551 no . . H4 H15 2.8118 no . . H7 H9 3.5113 no . . H7 H13 2.8794 no . . H9 H10 2.3333 no . . H12 H13 2.3510 no . . H15 H16 2.3329 no . . H18 H19 2.3290 no . . Br11 H18 3.1644 no . 1_345 Br11 H19 3.2216 no . 2_565 Br17 H7 3.0184 no . 1_665 Br17 H12 3.3696 no . 1_765 F1 H9 2.5465 no . 2_565 F1 H10 2.6119 no . 2_565 F2 H4 3.1934 no . 1_455 F2 H10 3.4309 no . 2_465 F2 H19 2.6641 no . 1_455 F3 H4 2.4990 no . 2_676 F3 H15 2.8600 no . 2_576 F4 H4 3.4120 no . 1_455 F4 H4 3.0626 no . 2_576 F4 H15 2.8246 no . 2_576 F5 H7 3.4782 no . 1_655 F5 H13 2.5142 no . 1_655 F5 H16 3.5832 no . 2_676 F6 H15 2.8975 no . 2_576 F6 H16 2.6698 no . 2_576 O1 H9 3.2036 no . 2_565 O3 H10 3.0409 no . 2_565 O3 H19 3.5225 no . 1_455 C1 H13 3.3843 no . 1_655 C2 H9 3.5783 no . 2_565 C5 H15 3.3914 no . 2_576 C6 H13 3.3132 no . 1_655 C7 H13 2.9698 no . 1_655 C9 H12 3.2692 no . 1_655 C10 H12 3.4713 no . 1_655 C12 H9 3.2366 no . 1_455 C13 H9 3.4226 no . 1_455 C15 H18 3.0174 no . 1_455 C16 H18 3.3866 no . 1_455 C18 H15 3.0289 no . 1_655 C19 H15 3.3880 no . 1_655 H4 F2 3.1934 no . 1_655 H4 F3 2.4990 no . 2_676 H4 F4 3.4120 no . 1_655 H4 F4 3.0626 no . 2_576 H4 H4 3.3045 no . 2_676 H7 Br17 3.0184 no . 1_445 H7 F5 3.4782 no . 1_455 H7 H12 3.3486 no . 1_655 H7 H13 3.0014 no . 1_655 H9 F1 2.5465 no . 2_565 H9 O1 3.2036 no . 2_565 H9 C2 3.5783 no . 2_565 H9 C12 3.2366 no . 1_655 H9 C13 3.4226 no . 1_655 H9 H9 3.0271 no . 2_565 H9 H12 3.1593 no . 1_655 H9 H13 3.4357 no . 1_655 H10 F1 2.6119 no . 2_565 H10 F2 3.4309 no . 2_465 H10 O3 3.0409 no . 2_565 H10 H12 3.5044 no . 1_655 H10 H19 3.1195 no . 2_565 H12 Br17 3.3696 no . 1_345 H12 C9 3.2692 no . 1_455 H12 C10 3.4713 no . 1_455 H12 H7 3.3486 no . 1_455 H12 H9 3.1593 no . 1_455 H12 H10 3.5044 no . 1_455 H12 H18 2.8896 no . 1_345 H13 F5 2.5142 no . 1_455 H13 C1 3.3843 no . 1_455 H13 C6 3.3132 no . 1_455 H13 C7 2.9698 no . 1_455 H13 H7 3.0014 no . 1_455 H13 H9 3.4357 no . 1_455 H15 F3 2.8600 no . 2_576 H15 F4 2.8246 no . 2_576 H15 F6 2.8975 no . 2_576 H15 C5 3.3914 no . 2_576 H15 C18 3.0289 no . 1_455 H15 C19 3.3880 no . 1_455 H15 H18 2.8576 no . 1_455 H15 H19 3.4638 no . 1_455 H16 F5 3.5832 no . 2_676 H16 F6 2.6698 no . 2_576 H16 H18 3.4838 no . 1_455 H18 Br11 3.1644 no . 1_765 H18 C15 3.0174 no . 1_655 H18 C16 3.3866 no . 1_655 H18 H12 2.8896 no . 1_765 H18 H15 2.8576 no . 1_655 H18 H16 3.4838 no . 1_655 H19 Br11 3.2216 no . 2_565 H19 F2 2.6641 no . 1_655 H19 O3 3.5225 no . 1_655 H19 H10 3.1195 no . 2_565 H19 H15 3.4638 no . 1_655 data_5b _database_code_depnum_ccdc_archive 'CCDC 916379' #TrackingRef '5b.cif' _chemical_formula_sum 'C18 H10 Br2 F4 O2' _chemical_formula_moiety 'C18 H10 Br2 F4 O2' _chemical_formula_weight 494.08 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 10.8993(14) _cell_length_b 12.8061(17) _cell_length_c 13.1597(17) _cell_angle_alpha 75.917(7) _cell_angle_beta 71.005(8) _cell_angle_gamma 89.973(6) _cell_volume 1678.4(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10660 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 25.43 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.030 _exptl_crystal_density_diffrn 1.955 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960.00 _exptl_absorpt_coefficient_mu 4.896 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.599 _exptl_absorpt_correction_T_max 0.863 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Saturn70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.286 _diffrn_reflns_number 16480 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_theta_max 25.35 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # 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 6102 _reflns_number_gt 3765 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1195 _refine_ls_wR_factor_ref 0.3703 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 6102 _refine_ls_number_parameters 469 _refine_ls_goodness_of_fit_ref 1.310 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.2000P)^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 0.023 _refine_diff_density_max 4.170 _refine_diff_density_min -1.650 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 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) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Br Br -0.2901 2.4595 ; 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 Br10 Br 0.30649(13) 0.54681(14) 0.06241(11) 0.0533(5) Uani 1.0 2 d . . . Br16 Br 0.20249(13) 0.29581(14) 0.93105(12) 0.0613(6) Uani 1.0 2 d . . . Br30 Br 0.80198(12) 1.17771(11) 0.06541(10) 0.0463(5) Uani 1.0 2 d . . . Br36 Br 0.70518(12) 0.98530(12) 0.93236(11) 0.0474(5) Uani 1.0 2 d . . . F1 F 0.3988(8) 0.9008(7) 0.5504(7) 0.062(3) Uani 1.0 2 d . . . F2 F 0.3433(8) 1.0283(7) 0.4364(7) 0.072(3) Uani 1.0 2 d . . . F3 F 0.0279(8) 0.8415(8) 0.4835(7) 0.066(3) Uani 1.0 2 d . . . F4 F 0.1310(9) 0.9923(8) 0.4016(7) 0.073(3) Uani 1.0 2 d . . . F21 F 0.8990(8) 0.5750(8) 0.5487(8) 0.073(3) Uani 1.0 2 d . . . F22 F 0.8461(9) 0.5066(8) 0.4309(8) 0.080(3) Uani 1.0 2 d . . . F23 F 0.5264(8) 0.6685(8) 0.4818(7) 0.072(3) Uani 1.0 2 d . . . F24 F 0.6343(9) 0.5580(8) 0.3978(8) 0.086(3) Uani 1.0 2 d . . . O1 O 0.3582(8) 0.8476(7) 0.3374(9) 0.052(3) Uani 1.0 2 d . . . O4 O 0.1081(9) 0.7459(8) 0.7312(8) 0.056(3) Uani 1.0 2 d . . . O21 O 0.8563(9) 0.7356(7) 0.3349(9) 0.057(3) Uani 1.0 2 d . . . O24 O 0.6100(10) 0.6393(8) 0.7289(9) 0.062(3) Uani 1.0 2 d . . . C1 C 0.2722(13) 0.8488(12) 0.4446(12) 0.053(4) Uani 1.0 2 d . . . C2 C 0.3129(16) 0.9265(12) 0.4998(12) 0.059(4) Uani 1.0 2 d . . . C3 C 0.1610(14) 0.9142(16) 0.5772(13) 0.077(6) Uani 1.0 2 d . . . C4 C 0.1659(13) 0.7841(11) 0.6233(12) 0.043(4) Uani 1.0 2 d . . . C5 C 0.2335(12) 0.7489(10) 0.5401(13) 0.051(4) Uani 1.0 2 d . . . C6 C 0.1304(14) 0.9036(12) 0.4704(12) 0.056(4) Uani 1.0 2 d . . . C7 C 0.3377(11) 0.7727(12) 0.2794(12) 0.051(4) Uani 1.0 2 d . . . C8 C 0.4472(13) 0.7554(12) 0.2024(12) 0.055(4) Uani 1.0 2 d . . . C9 C 0.4387(12) 0.6884(11) 0.1394(11) 0.043(4) Uani 1.0 2 d . . . C10 C 0.3195(12) 0.6359(12) 0.1566(11) 0.049(4) Uani 1.0 2 d . . . C11 C 0.2066(14) 0.6545(12) 0.2364(12) 0.058(4) Uani 1.0 2 d . . . C12 C 0.2164(14) 0.7232(13) 0.3029(13) 0.065(5) Uani 1.0 2 d . . . C13 C 0.1334(14) 0.6373(10) 0.7738(10) 0.045(4) Uani 1.0 2 d . . . C14 C 0.2630(13) 0.6126(11) 0.7635(12) 0.056(4) Uani 1.0 2 d . . . C15 C 0.2804(13) 0.5083(13) 0.8112(11) 0.052(4) Uani 1.0 2 d . . . C16 C 0.1801(12) 0.4364(10) 0.8675(11) 0.040(3) Uani 1.0 2 d . . . C17 C 0.0500(14) 0.4566(13) 0.8763(11) 0.058(4) Uani 1.0 2 d . . . C18 C 0.0307(14) 0.5639(15) 0.8279(13) 0.070(5) Uani 1.0 2 d . . . C21 C 0.7707(13) 0.6824(13) 0.4407(12) 0.053(4) Uani 1.0 2 d . . . C22 C 0.8078(18) 0.5744(12) 0.4992(13) 0.070(5) Uani 1.0 2 d . . . C23 C 0.6651(14) 0.5548(13) 0.5704(12) 0.059(4) Uani 1.0 2 d . . . C24 C 0.6695(15) 0.6507(10) 0.6209(14) 0.057(5) Uani 1.0 2 d . . . C25 C 0.7336(12) 0.7285(11) 0.5372(12) 0.049(4) Uani 1.0 2 d . . . C26 C 0.6337(16) 0.6128(12) 0.4699(12) 0.056(4) Uani 1.0 2 d . . . C27 C 0.8362(13) 0.8396(12) 0.2821(13) 0.054(4) Uani 1.0 2 d . . . C28 C 0.9488(13) 0.8974(13) 0.2059(12) 0.053(4) Uani 1.0 2 d . . . C29 C 0.9369(12) 1.0005(13) 0.1409(11) 0.049(4) Uani 1.0 2 d . . . C30 C 0.8126(11) 1.0449(11) 0.1520(11) 0.042(3) Uani 1.0 2 d . . . C31 C 0.7085(13) 0.9829(13) 0.2331(13) 0.059(4) Uani 1.0 2 d . . . C32 C 0.7131(13) 0.8814(12) 0.3031(13) 0.059(4) Uani 1.0 2 d . . . C33 C 0.6414(12) 0.7276(11) 0.7676(11) 0.045(4) Uani 1.0 2 d . . . C34 C 0.7652(15) 0.7503(12) 0.7613(12) 0.061(4) Uani 1.0 2 d . . . C35 C 0.7864(14) 0.8310(12) 0.8072(11) 0.053(4) Uani 1.0 2 d . . . C36 C 0.6802(11) 0.8819(10) 0.8581(10) 0.039(3) Uani 1.0 2 d . . . C37 C 0.5574(13) 0.8496(13) 0.8692(12) 0.053(4) Uani 1.0 2 d . . . C38 C 0.5363(13) 0.7760(12) 0.8218(11) 0.053(4) Uani 1.0 2 d . . . H3 H 0.1196 0.9636 0.6244 0.0922 Uiso 1.0 2 calc R . . H5 H 0.2540 0.6769 0.5392 0.0616 Uiso 1.0 2 calc R . . H8 H 0.5290 0.7897 0.1926 0.0661 Uiso 1.0 2 calc R . . H9 H 0.5145 0.6772 0.0832 0.0516 Uiso 1.0 2 calc R . . H11 H 0.1244 0.6214 0.2458 0.0695 Uiso 1.0 2 calc R . . H12 H 0.1429 0.7347 0.3609 0.0783 Uiso 1.0 2 calc R . . H14 H 0.3344 0.6658 0.7254 0.0677 Uiso 1.0 2 calc R . . H15 H 0.3661 0.4877 0.8035 0.0627 Uiso 1.0 2 calc R . . H17 H -0.0199 0.4017 0.9125 0.0697 Uiso 1.0 2 calc R . . H18 H -0.0548 0.5840 0.8337 0.0841 Uiso 1.0 2 calc R . . H23 H 0.6233 0.4815 0.6166 0.0703 Uiso 1.0 2 calc R . . H25 H 0.7528 0.8007 0.5378 0.0586 Uiso 1.0 2 calc R . . H28 H 1.0312 0.8694 0.1973 0.0638 Uiso 1.0 2 calc R . . H29 H 1.0135 1.0419 0.0882 0.0586 Uiso 1.0 2 calc R . . H31 H 0.6256 1.0105 0.2433 0.0709 Uiso 1.0 2 calc R . . H32 H 0.6378 0.8435 0.3609 0.0705 Uiso 1.0 2 calc R . . H34 H 0.8344 0.7120 0.7266 0.0734 Uiso 1.0 2 calc R . . H35 H 0.8715 0.8515 0.8042 0.0630 Uiso 1.0 2 calc R . . H37 H 0.4859 0.8806 0.9118 0.0638 Uiso 1.0 2 calc R . . H38 H 0.4508 0.7565 0.8248 0.0634 Uiso 1.0 2 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 Br10 0.0408(9) 0.0804(12) 0.0421(9) 0.0095(7) -0.0129(7) -0.0236(8) Br16 0.0414(9) 0.0743(12) 0.0514(10) -0.0011(7) -0.0140(7) 0.0121(8) Br30 0.0373(8) 0.0546(10) 0.0411(8) -0.0065(6) -0.0133(6) -0.0013(6) Br36 0.0350(8) 0.0653(10) 0.0472(9) 0.0070(7) -0.0139(7) -0.0237(7) F1 0.044(5) 0.057(6) 0.076(6) -0.002(4) -0.019(5) -0.004(5) F2 0.080(6) 0.035(5) 0.079(6) -0.007(5) -0.002(5) -0.006(5) F3 0.054(5) 0.079(7) 0.072(6) 0.018(5) -0.023(5) -0.031(5) F4 0.091(7) 0.074(7) 0.062(6) 0.040(6) -0.031(5) -0.021(5) F21 0.056(6) 0.097(8) 0.082(7) 0.027(5) -0.033(5) -0.035(6) F22 0.078(7) 0.069(7) 0.089(7) 0.010(5) -0.009(5) -0.042(6) F23 0.066(6) 0.075(7) 0.063(6) -0.006(5) -0.019(5) -0.002(5) F24 0.092(7) 0.072(7) 0.088(7) -0.024(6) -0.025(6) -0.016(6) O1 0.038(5) 0.033(5) 0.093(8) 0.002(4) -0.024(6) -0.027(5) O4 0.056(6) 0.047(6) 0.068(7) 0.020(5) -0.024(6) -0.017(5) O21 0.039(6) 0.033(6) 0.105(9) 0.006(4) -0.033(6) -0.014(6) O24 0.079(8) 0.046(6) 0.062(7) -0.005(6) -0.024(6) -0.012(5) C1 0.041(8) 0.056(10) 0.062(10) 0.007(7) -0.015(8) -0.016(8) C2 0.065(11) 0.037(9) 0.064(10) -0.010(7) -0.002(8) -0.021(8) C3 0.044(9) 0.121(17) 0.057(10) 0.006(10) -0.020(8) -0.003(10) C4 0.054(9) 0.034(8) 0.065(10) 0.017(7) -0.040(8) -0.027(7) C5 0.049(9) 0.026(7) 0.098(12) 0.014(6) -0.044(9) -0.025(8) C6 0.046(9) 0.040(9) 0.057(10) -0.005(7) 0.018(8) -0.017(8) C7 0.018(7) 0.057(9) 0.075(10) 0.009(6) -0.021(7) -0.005(8) C8 0.044(9) 0.056(10) 0.056(9) -0.021(7) -0.021(8) 0.006(8) C9 0.028(7) 0.049(9) 0.040(8) 0.002(6) -0.005(6) -0.000(7) C10 0.028(7) 0.069(10) 0.047(8) 0.005(7) -0.016(7) -0.005(7) C11 0.045(8) 0.058(10) 0.079(11) 0.000(7) -0.022(8) -0.030(9) C12 0.044(9) 0.080(12) 0.089(12) 0.011(8) -0.019(9) -0.056(10) C13 0.067(9) 0.024(7) 0.038(8) 0.005(6) -0.008(7) -0.009(6) C14 0.045(8) 0.030(8) 0.090(12) 0.002(6) -0.025(8) -0.004(8) C15 0.030(7) 0.070(11) 0.063(10) 0.008(7) -0.021(7) -0.022(8) C16 0.048(8) 0.027(7) 0.050(8) 0.016(6) -0.022(7) -0.009(6) C17 0.053(9) 0.072(11) 0.050(9) 0.013(8) -0.028(8) -0.004(8) C18 0.036(9) 0.093(14) 0.075(11) -0.015(9) -0.000(8) -0.035(11) C21 0.046(9) 0.061(10) 0.047(9) -0.002(7) -0.015(7) -0.008(8) C22 0.100(14) 0.042(9) 0.076(12) 0.036(9) -0.033(11) -0.026(9) C23 0.052(9) 0.061(10) 0.053(9) 0.006(8) -0.009(8) -0.011(8) C24 0.075(11) 0.018(7) 0.088(12) -0.016(7) -0.056(10) 0.009(7) C25 0.040(8) 0.039(8) 0.075(10) 0.013(6) -0.019(8) -0.028(8) C26 0.073(11) 0.048(9) 0.041(8) 0.018(8) 0.003(8) -0.031(7) C27 0.042(8) 0.043(8) 0.091(11) 0.012(7) -0.024(8) -0.040(8) C28 0.039(8) 0.084(12) 0.052(9) 0.020(8) -0.023(7) -0.035(9) C29 0.019(7) 0.087(12) 0.043(8) 0.012(7) -0.008(6) -0.025(8) C30 0.029(7) 0.044(8) 0.052(8) -0.006(6) -0.007(6) -0.022(7) C31 0.030(8) 0.062(10) 0.093(12) 0.007(7) -0.028(8) -0.025(9) C32 0.043(8) 0.043(9) 0.080(11) 0.000(7) -0.008(8) -0.014(8) C33 0.040(8) 0.037(8) 0.070(10) 0.002(6) -0.031(8) -0.021(7) C34 0.080(11) 0.039(9) 0.073(11) 0.015(8) -0.029(9) -0.024(8) C35 0.054(9) 0.049(9) 0.065(10) 0.015(7) -0.027(8) -0.025(8) C36 0.038(7) 0.046(8) 0.040(7) 0.001(6) -0.027(6) -0.006(6) C37 0.042(8) 0.065(10) 0.058(9) 0.006(7) -0.029(7) -0.010(8) C38 0.033(8) 0.053(9) 0.054(9) -0.003(7) -0.007(7) 0.007(7) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _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 Br10 C10 1.913(17) yes . . Br16 C16 1.844(12) yes . . Br30 C30 1.829(13) yes . . Br36 C36 1.894(15) yes . . F1 C2 1.31(2) yes . . F2 C2 1.340(15) yes . . F3 C6 1.310(18) yes . . F4 C6 1.267(16) yes . . F21 C22 1.35(3) yes . . F22 C22 1.37(2) yes . . F23 C26 1.354(19) yes . . F24 C26 1.31(2) yes . . O1 C1 1.421(17) yes . . O1 C7 1.42(2) yes . . O4 C4 1.316(16) yes . . O4 C13 1.430(16) yes . . O21 C21 1.402(15) yes . . O21 C27 1.397(17) yes . . O24 C24 1.327(19) yes . . O24 C33 1.43(2) yes . . C1 C2 1.51(3) yes . . C1 C5 1.505(18) yes . . C1 C6 1.66(2) yes . . C2 C3 1.62(2) yes . . C3 C4 1.64(3) yes . . C3 C6 1.58(3) yes . . C4 C5 1.29(2) yes . . C7 C8 1.351(18) yes . . C7 C12 1.37(2) yes . . C8 C9 1.35(3) yes . . C9 C10 1.388(19) yes . . C10 C11 1.399(18) yes . . C11 C12 1.41(3) yes . . C13 C14 1.42(2) yes . . C13 C18 1.342(19) yes . . C14 C15 1.37(2) yes . . C15 C16 1.317(17) yes . . C16 C17 1.41(2) yes . . C17 C18 1.41(3) yes . . C21 C22 1.53(3) yes . . C21 C25 1.47(3) yes . . C21 C26 1.62(3) yes . . C22 C23 1.52(2) yes . . C23 C24 1.54(3) yes . . C23 C26 1.49(3) yes . . C24 C25 1.289(17) yes . . C27 C28 1.378(17) yes . . C27 C32 1.41(2) yes . . C28 C29 1.42(2) yes . . C29 C30 1.447(18) yes . . C30 C31 1.363(16) yes . . C31 C32 1.41(2) yes . . C33 C34 1.35(3) yes . . C33 C38 1.374(19) yes . . C34 C35 1.37(3) yes . . C35 C36 1.385(19) yes . . C36 C37 1.35(2) yes . . C37 C38 1.31(3) yes . . C3 H3 1.000 no . . C5 H5 0.950 no . . C8 H8 0.950 no . . C9 H9 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C14 H14 0.950 no . . C15 H15 0.950 no . . C17 H17 0.950 no . . C18 H18 0.950 no . . C23 H23 1.000 no . . C25 H25 0.950 no . . C28 H28 0.950 no . . C29 H29 0.950 no . . C31 H31 0.950 no . . C32 H32 0.950 no . . C34 H34 0.950 no . . C35 H35 0.950 no . . C37 H37 0.950 no . . C38 H38 0.950 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 C1 O1 C7 122.5(10) yes . . . C4 O4 C13 114.1(11) yes . . . C21 O21 C27 120.5(11) yes . . . C24 O24 C33 113.6(10) yes . . . O1 C1 C2 116.3(11) yes . . . O1 C1 C5 122.1(13) yes . . . O1 C1 C6 125.3(13) yes . . . C2 C1 C5 99.9(13) yes . . . C2 C1 C6 86.6(12) yes . . . C5 C1 C6 98.9(9) yes . . . F1 C2 F2 109.3(13) yes . . . F1 C2 C1 120.0(13) yes . . . F1 C2 C3 117.2(12) yes . . . F2 C2 C1 114.1(14) yes . . . F2 C2 C3 108.5(13) yes . . . C1 C2 C3 85.8(13) yes . . . C2 C3 C4 91.1(12) yes . . . C2 C3 C6 85.8(11) yes . . . C4 C3 C6 94.1(14) yes . . . O4 C4 C3 114.7(12) yes . . . O4 C4 C5 137.9(13) yes . . . C3 C4 C5 107.4(11) yes . . . C1 C5 C4 103.6(12) yes . . . F3 C6 F4 108.1(14) yes . . . F3 C6 C1 116.7(13) yes . . . F3 C6 C3 118.7(11) yes . . . F4 C6 C1 114.5(10) yes . . . F4 C6 C3 115.2(15) yes . . . C1 C6 C3 82.1(12) yes . . . O1 C7 C8 113.8(12) yes . . . O1 C7 C12 121.5(12) yes . . . C8 C7 C12 124.7(17) yes . . . C7 C8 C9 119.0(14) yes . . . C8 C9 C10 120.1(12) yes . . . Br10 C10 C9 119.9(10) yes . . . Br10 C10 C11 119.4(12) yes . . . C9 C10 C11 120.4(15) yes . . . C10 C11 C12 119.1(14) yes . . . C7 C12 C11 116.5(13) yes . . . O4 C13 C14 119.6(11) yes . . . O4 C13 C18 117.6(14) yes . . . C14 C13 C18 122.8(13) yes . . . C13 C14 C15 116.9(11) yes . . . C14 C15 C16 120.9(13) yes . . . Br16 C16 C15 121.2(11) yes . . . Br16 C16 C17 114.7(9) yes . . . C15 C16 C17 123.8(13) yes . . . C16 C17 C18 115.6(12) yes . . . C13 C18 C17 119.8(14) yes . . . O21 C21 C22 117.5(12) yes . . . O21 C21 C25 124.4(13) yes . . . O21 C21 C26 127.2(14) yes . . . C22 C21 C25 96.4(12) yes . . . C22 C21 C26 83.0(12) yes . . . C25 C21 C26 97.8(10) yes . . . F21 C22 F22 106.3(14) yes . . . F21 C22 C21 119.1(14) yes . . . F21 C22 C23 119.3(14) yes . . . F22 C22 C21 112.4(14) yes . . . F22 C22 C23 113.6(15) yes . . . C21 C22 C23 85.4(12) yes . . . C22 C23 C24 93.8(13) yes . . . C22 C23 C26 88.0(11) yes . . . C24 C23 C26 98.9(13) yes . . . O24 C24 C23 119.9(11) yes . . . O24 C24 C25 135.7(15) yes . . . C23 C24 C25 104.3(14) yes . . . C21 C25 C24 105.6(14) yes . . . F23 C26 F24 105.9(14) yes . . . F23 C26 C21 116.5(12) yes . . . F23 C26 C23 119.8(12) yes . . . F24 C26 C21 113.7(11) yes . . . F24 C26 C23 117.0(13) yes . . . C21 C26 C23 83.0(12) yes . . . O21 C27 C28 113.2(12) yes . . . O21 C27 C32 123.8(11) yes . . . C28 C27 C32 123.0(13) yes . . . C27 C28 C29 117.5(13) yes . . . C28 C29 C30 122.4(10) yes . . . Br30 C30 C29 120.8(8) yes . . . Br30 C30 C31 124.0(11) yes . . . C29 C30 C31 115.1(12) yes . . . C30 C31 C32 125.7(13) yes . . . C27 C32 C31 116.0(11) yes . . . O24 C33 C34 120.3(13) yes . . . O24 C33 C38 115.1(13) yes . . . C34 C33 C38 124.2(16) yes . . . C33 C34 C35 117.1(14) yes . . . C34 C35 C36 118.2(15) yes . . . Br36 C36 C35 118.8(11) yes . . . Br36 C36 C37 118.8(11) yes . . . C35 C36 C37 121.8(15) yes . . . C36 C37 C38 120.5(14) yes . . . C33 C38 C37 118.0(14) yes . . . C2 C3 H3 124.963 no . . . C4 C3 H3 124.958 no . . . C6 C3 H3 124.964 no . . . C1 C5 H5 128.218 no . . . C4 C5 H5 128.218 no . . . C7 C8 H8 120.517 no . . . C9 C8 H8 120.527 no . . . C8 C9 H9 119.931 no . . . C10 C9 H9 119.932 no . . . C10 C11 H11 120.436 no . . . C12 C11 H11 120.432 no . . . C7 C12 H12 121.750 no . . . C11 C12 H12 121.759 no . . . C13 C14 H14 121.538 no . . . C15 C14 H14 121.534 no . . . C14 C15 H15 119.560 no . . . C16 C15 H15 119.561 no . . . C16 C17 H17 122.175 no . . . C18 C17 H17 122.182 no . . . C13 C18 H18 120.106 no . . . C17 C18 H18 120.116 no . . . C22 C23 H23 122.586 no . . . C24 C23 H23 122.587 no . . . C26 C23 H23 122.589 no . . . C21 C25 H25 127.192 no . . . C24 C25 H25 127.201 no . . . C27 C28 H28 121.261 no . . . C29 C28 H28 121.251 no . . . C28 C29 H29 118.799 no . . . C30 C29 H29 118.806 no . . . C30 C31 H31 117.146 no . . . C32 C31 H31 117.145 no . . . C27 C32 H32 121.988 no . . . C31 C32 H32 121.993 no . . . C33 C34 H34 121.462 no . . . C35 C34 H34 121.481 no . . . C34 C35 H35 120.921 no . . . C36 C35 H35 120.923 no . . . C36 C37 H37 119.754 no . . . C38 C37 H37 119.742 no . . . C33 C38 H38 121.008 no . . . C37 C38 H38 120.997 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 C1 O1 C7 C8 -156.6(11) no . . . . C1 O1 C7 C12 22.7(19) no . . . . C7 O1 C1 C2 174.9(11) no . . . . C7 O1 C1 C5 52.5(19) no . . . . C7 O1 C1 C6 -79.5(16) no . . . . C4 O4 C13 C14 61.0(17) no . . . . C4 O4 C13 C18 -122.7(13) no . . . . C13 O4 C4 C3 -168.9(11) no . . . . C13 O4 C4 C5 7(3) no . . . . C21 O21 C27 C28 154.6(13) no . . . . C21 O21 C27 C32 -26(3) no . . . . C27 O21 C21 C22 -172.8(13) no . . . . C27 O21 C21 C25 -52(2) no . . . . C27 O21 C21 C26 84.4(19) no . . . . C24 O24 C33 C34 -62.6(16) no . . . . C24 O24 C33 C38 124.9(12) no . . . . C33 O24 C24 C23 169.4(12) no . . . . C33 O24 C24 C25 -13(3) no . . . . O1 C1 C2 F1 -80.5(15) no . . . . O1 C1 C2 F2 52.0(18) no . . . . O1 C1 C2 C3 160.4(11) no . . . . O1 C1 C5 C4 174.5(13) no . . . . O1 C1 C6 F3 88.2(16) no . . . . O1 C1 C6 F4 -39(3) no . . . . O1 C1 C6 C3 -153.6(14) no . . . . C2 C1 C5 C4 44.7(13) no . . . . C5 C1 C2 F1 53.0(14) no . . . . C5 C1 C2 F2 -174.6(11) no . . . . C5 C1 C2 C3 -66.2(10) no . . . . C2 C1 C6 F3 -151.7(12) no . . . . C2 C1 C6 F4 80.7(14) no . . . . C2 C1 C6 C3 -33.5(8) no . . . . C6 C1 C2 F1 151.5(11) no . . . . C6 C1 C2 F2 -76.1(12) no . . . . C6 C1 C2 C3 32.3(8) no . . . . C5 C1 C6 F3 -52.2(17) no . . . . C5 C1 C6 F4 -179.9(14) no . . . . C5 C1 C6 C3 66.0(12) no . . . . C6 C1 C5 C4 -43.4(15) no . . . . F1 C2 C3 C4 -61.9(15) no . . . . F1 C2 C3 C6 -156.0(12) no . . . . F2 C2 C3 C4 173.8(13) no . . . . F2 C2 C3 C6 79.7(14) no . . . . C1 C2 C3 C4 59.8(11) no . . . . C1 C2 C3 C6 -34.3(10) no . . . . C2 C3 C4 O4 136.3(13) no . . . . C2 C3 C4 C5 -40.8(15) no . . . . C2 C3 C6 F3 147.1(12) no . . . . C2 C3 C6 F4 -82.5(13) no . . . . C2 C3 C6 C1 30.9(9) no . . . . C4 C3 C6 F3 56.3(14) no . . . . C4 C3 C6 F4 -173.2(10) no . . . . C4 C3 C6 C1 -59.8(8) no . . . . C6 C3 C4 O4 -137.9(12) no . . . . C6 C3 C4 C5 45.1(13) no . . . . O4 C4 C5 C1 -175.6(19) no . . . . C3 C4 C5 C1 0.4(16) no . . . . O1 C7 C8 C9 -177.8(11) no . . . . O1 C7 C12 C11 177.0(11) no . . . . C8 C7 C12 C11 -4(3) no . . . . C12 C7 C8 C9 3(3) no . . . . C7 C8 C9 C10 -2(2) no . . . . C8 C9 C10 Br10 176.9(11) no . . . . C8 C9 C10 C11 2(2) no . . . . Br10 C10 C11 C12 -177.8(9) no . . . . C9 C10 C11 C12 -3(2) no . . . . C10 C11 C12 C7 4(2) no . . . . O4 C13 C14 C15 176.6(12) no . . . . O4 C13 C18 C17 -177.0(13) no . . . . C14 C13 C18 C17 -1(3) no . . . . C18 C13 C14 C15 1(3) no . . . . C13 C14 C15 C16 -3(3) no . . . . C14 C15 C16 Br16 179.6(13) no . . . . C14 C15 C16 C17 5(3) no . . . . Br16 C16 C17 C18 -179.9(9) no . . . . C15 C16 C17 C18 -5(3) no . . . . C16 C17 C18 C13 3(3) no . . . . O21 C21 C22 F21 78.1(19) no . . . . O21 C21 C22 F22 -47(2) no . . . . O21 C21 C22 C23 -160.9(14) no . . . . O21 C21 C25 C24 -171.3(12) no . . . . O21 C21 C26 F23 -87.8(18) no . . . . O21 C21 C26 F24 36(2) no . . . . O21 C21 C26 C23 152.3(14) no . . . . C22 C21 C25 C24 -41.5(13) no . . . . C25 C21 C22 F21 -56.3(14) no . . . . C25 C21 C22 F22 178.5(12) no . . . . C25 C21 C22 C23 64.8(11) no . . . . C22 C21 C26 F23 152.9(13) no . . . . C22 C21 C26 F24 -83.5(13) no . . . . C22 C21 C26 C23 33.0(10) no . . . . C26 C21 C22 F21 -153.4(13) no . . . . C26 C21 C22 F22 81.4(14) no . . . . C26 C21 C22 C23 -32.3(10) no . . . . C25 C21 C26 F23 57.3(14) no . . . . C25 C21 C26 F24 -179.1(11) no . . . . C25 C21 C26 C23 -62.6(10) no . . . . C26 C21 C25 C24 42.2(13) no . . . . F21 C22 C23 C24 57.4(15) no . . . . F21 C22 C23 C26 156.1(13) no . . . . F22 C22 C23 C24 -176.0(12) no . . . . F22 C22 C23 C26 -77.3(14) no . . . . C21 C22 C23 C24 -63.5(12) no . . . . C21 C22 C23 C26 35.2(12) no . . . . C22 C23 C24 O24 -137.0(15) no . . . . C22 C23 C24 C25 44.9(15) no . . . . C22 C23 C26 F23 -149.7(14) no . . . . C22 C23 C26 F24 79.9(14) no . . . . C22 C23 C26 C21 -33.2(10) no . . . . C24 C23 C26 F23 -56.2(16) no . . . . C24 C23 C26 F24 173.4(11) no . . . . C24 C23 C26 C21 60.4(10) no . . . . C26 C23 C24 O24 134.4(14) no . . . . C26 C23 C24 C25 -43.7(14) no . . . . O24 C24 C25 C21 -179.4(18) no . . . . C23 C24 C25 C21 -1.8(16) no . . . . O21 C27 C28 C29 174.6(13) no . . . . O21 C27 C32 C31 -172.8(14) no . . . . C28 C27 C32 C31 6(3) no . . . . C32 C27 C28 C29 -5(3) no . . . . C27 C28 C29 C30 -0(3) no . . . . C28 C29 C30 Br30 -179.5(13) no . . . . C28 C29 C30 C31 3(3) no . . . . Br30 C30 C31 C32 -178.5(11) no . . . . C29 C30 C31 C32 -1(3) no . . . . C30 C31 C32 C27 -3(3) no . . . . O24 C33 C34 C35 -175.5(10) no . . . . O24 C33 C38 C37 173.1(10) no . . . . C34 C33 C38 C37 1(2) no . . . . C38 C33 C34 C35 -4(2) no . . . . C33 C34 C35 C36 1.1(18) no . . . . C34 C35 C36 Br36 175.0(10) no . . . . C34 C35 C36 C37 4.1(18) no . . . . Br36 C36 C37 C38 -178.0(9) no . . . . C35 C36 C37 C38 -7(2) no . . . . C36 C37 C38 C33 4(2) no . . . . 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 F1 O1 3.202(16) no . . F1 O4 3.527(11) no . . F1 C4 2.704(16) no . . F1 C5 2.709(18) no . . F1 C6 3.41(2) no . . F2 F4 2.563(14) no . . F2 O1 2.900(15) no . . F2 C4 3.568(14) no . . F2 C5 3.558(15) no . . F2 C6 2.667(18) no . . F3 O1 3.475(11) no . . F3 O4 3.577(15) no . . F3 C2 3.38(2) no . . F3 C4 2.71(2) no . . F3 C5 2.763(17) no . . F3 C12 3.276(19) no . . F4 O1 3.111(13) no . . F4 C2 2.73(2) no . . F4 C4 3.564(17) no . . F4 C5 3.584(16) no . . F21 O21 3.225(14) no . . F21 O24 3.508(13) no . . F21 C24 2.645(18) no . . F21 C25 2.677(17) no . . F21 C26 3.37(2) no . . F22 F24 2.542(15) no . . F22 O21 2.883(13) no . . F22 C24 3.531(19) no . . F22 C25 3.514(18) no . . F22 C26 2.652(19) no . . F23 O21 3.474(11) no . . F23 O24 3.589(16) no . . F23 C22 3.35(3) no . . F23 C24 2.74(3) no . . F23 C25 2.751(19) no . . F23 C32 3.298(15) no . . F24 O21 3.082(14) no . . F24 C22 2.68(3) no . . F24 C24 3.55(3) no . . F24 C25 3.54(2) no . . O1 C3 3.49(2) no . . O1 C4 3.548(17) no . . O1 C9 3.579(19) no . . O4 C1 3.514(16) no . . O4 C2 3.430(15) no . . O4 C6 3.465(18) no . . O21 C23 3.408(15) no . . O21 C24 3.538(18) no . . O24 C21 3.524(17) no . . O24 C22 3.384(19) no . . O24 C26 3.43(2) no . . O24 C37 3.57(2) no . . C1 C12 2.94(3) no . . C4 C14 2.94(2) no . . C4 C18 3.332(19) no . . C5 C7 3.18(3) no . . C5 C12 3.28(3) no . . C5 C13 2.893(18) no . . C5 C14 3.15(3) no . . C6 C7 3.55(2) no . . C6 C12 3.49(3) no . . C7 C10 2.70(3) no . . C8 C11 2.78(2) no . . C9 C12 2.788(18) no . . C13 C16 2.695(17) no . . C14 C17 2.811(19) no . . C15 C18 2.77(2) no . . C21 C28 3.586(18) no . . C21 C32 2.94(2) no . . C24 C34 2.92(3) no . . C24 C38 3.35(3) no . . C25 C27 3.13(2) no . . C25 C32 3.30(2) no . . C25 C33 2.86(2) no . . C25 C34 3.16(3) no . . C26 C27 3.519(18) no . . C26 C32 3.535(19) no . . C27 C30 2.830(19) no . . C28 C31 2.79(2) no . . C29 C32 2.804(16) no . . C33 C36 2.64(3) no . . C34 C37 2.75(2) no . . C35 C38 2.75(3) no . . Br10 O24 3.534(11) no . 2_666 Br10 C15 3.557(17) no . 1_554 Br16 C35 3.473(15) no . 2_667 Br30 O4 3.474(12) no . 2_676 F1 F1 3.090(11) no . 2_676 F1 F2 3.026(13) no . 2_676 F1 F23 3.476(14) no . . F1 C31 3.41(2) no . 2_676 F2 F1 3.026(13) no . 2_676 F2 C25 3.295(17) no . 2_676 F2 C33 3.554(15) no . 2_676 F2 C38 3.537(14) no . 2_676 F3 F4 3.111(14) no . 2_576 F3 F21 3.486(14) no . 1_455 F3 O21 3.583(16) no . 1_455 F3 C25 3.304(16) no . 1_455 F4 F3 3.111(14) no . 2_576 F4 F4 3.215(11) no . 2_576 F4 C3 3.350(19) no . 2_576 F4 C6 3.270(17) no . 2_576 F4 C34 3.425(15) no . 2_676 F4 C35 2.974(15) no . 2_676 F4 C36 3.355(13) no . 2_676 F21 F3 3.486(14) no . 1_655 F21 F21 3.089(14) no . 2_766 F21 F22 3.038(14) no . 2_766 F21 C11 3.436(16) no . 2_666 F22 F21 3.038(14) no . 2_766 F22 C5 3.284(17) no . 2_666 F22 C13 3.567(19) no . 2_666 F22 C18 3.57(2) no . 2_666 F23 F1 3.476(14) no . . F23 F24 3.155(13) no . 2_666 F23 O1 3.518(14) no . . F23 C5 3.261(16) no . . F24 F23 3.155(13) no . 2_666 F24 F24 3.308(11) no . 2_666 F24 C14 3.354(19) no . 2_666 F24 C15 2.937(19) no . 2_666 F24 C16 3.401(15) no . 2_666 F24 C23 3.425(19) no . 2_666 F24 C26 3.344(17) no . 2_666 O1 F23 3.518(14) no . . O4 Br30 3.474(12) no . 2_676 O4 C35 3.568(17) no . 1_455 O21 F3 3.583(16) no . 1_655 O24 Br10 3.534(11) no . 2_666 C3 F4 3.350(19) no . 2_576 C5 F22 3.284(17) no . 2_666 C5 F23 3.261(16) no . . C6 F4 3.270(17) no . 2_576 C9 C37 3.466(17) no . 1_554 C11 F21 3.436(16) no . 2_666 C13 F22 3.567(19) no . 2_666 C14 F24 3.354(19) no . 2_666 C15 Br10 3.557(17) no . 1_556 C15 F24 2.937(19) no . 2_666 C16 F24 3.401(15) no . 2_666 C17 C17 3.53(3) no . 2_567 C18 F22 3.57(2) no . 2_666 C23 F24 3.425(19) no . 2_666 C25 F2 3.295(17) no . 2_676 C25 F3 3.304(16) no . 1_655 C26 F24 3.344(17) no . 2_666 C29 C29 3.51(2) no . 2_775 C31 F1 3.41(2) no . 2_676 C33 F2 3.554(15) no . 2_676 C34 F4 3.425(15) no . 2_676 C35 Br16 3.473(15) no . 2_667 C35 F4 2.974(15) no . 2_676 C35 O4 3.568(17) no . 1_655 C36 F4 3.355(13) no . 2_676 C37 C9 3.466(17) no . 1_556 C38 F2 3.537(14) no . 2_676 Br10 H9 2.9384 no . . Br10 H11 2.9452 no . . Br16 H15 2.8431 no . . Br16 H17 2.8276 no . . Br30 H29 2.9362 no . . Br30 H31 2.8981 no . . Br36 H35 2.9124 no . . Br36 H37 2.8609 no . . F1 H3 3.0511 no . . F1 H5 3.3301 no . . F1 H14 3.2287 no . . F2 H3 2.7984 no . . F3 H3 3.0822 no . . F3 H5 3.3863 no . . F3 H12 2.4081 no . . F4 H3 2.8264 no . . F4 H12 3.4640 no . . F21 H23 2.9994 no . . F21 H25 3.2944 no . . F21 H34 3.1586 no . . F22 H23 2.7799 no . . F23 H23 3.0242 no . . F23 H25 3.3605 no . . F23 H32 2.4568 no . . F24 H23 2.7687 no . . F24 H32 3.5673 no . . O1 H5 2.8866 no . . O1 H8 2.4542 no . . O1 H12 2.6456 no . . O4 H3 2.7829 no . . O4 H5 2.8563 no . . O4 H14 2.6561 no . . O4 H18 2.5203 no . . O21 H25 2.8664 no . . O21 H28 2.4691 no . . O21 H32 2.7186 no . . O24 H23 2.7573 no . . O24 H25 2.8186 no . . O24 H34 2.6055 no . . O24 H38 2.5196 no . . C1 H3 3.1074 no . . C1 H12 2.6694 no . . C2 H5 3.1428 no . . C3 H5 3.3034 no . . C4 H14 2.8433 no . . C4 H18 3.4984 no . . C5 H3 3.3043 no . . C5 H12 2.8789 no . . C5 H14 2.9615 no . . C6 H5 3.2518 no . . C6 H12 2.8568 no . . C7 H5 3.1552 no . . C7 H9 3.1889 no . . C7 H11 3.2322 no . . C8 H12 3.2638 no . . C9 H11 3.2759 no . . C10 H8 3.2375 no . . C10 H12 3.2899 no . . C11 H9 3.2746 no . . C12 H5 3.1813 no . . C12 H8 3.2591 no . . C13 H5 2.8484 no . . C13 H15 3.2452 no . . C13 H17 3.2497 no . . C14 H5 2.8995 no . . C14 H18 3.2765 no . . C15 H17 3.2607 no . . C16 H14 3.2006 no . . C16 H18 3.2634 no . . C17 H15 3.2577 no . . C18 H14 3.2748 no . . C21 H23 3.0402 no . . C21 H32 2.7183 no . . C22 H25 3.0867 no . . C23 H25 3.1769 no . . C24 H34 2.8181 no . . C24 H38 3.5101 no . . C25 H23 3.1813 no . . C25 H32 2.9243 no . . C25 H34 2.9985 no . . C26 H25 3.1751 no . . C26 H32 2.9470 no . . C27 H25 3.0964 no . . C27 H29 3.2456 no . . C27 H31 3.2451 no . . C28 H32 3.3077 no . . C29 H31 3.2331 no . . C30 H28 3.3696 no . . C30 H32 3.3147 no . . C31 H29 3.2297 no . . C32 H25 3.1800 no . . C32 H28 3.3088 no . . C33 H25 2.7807 no . . C33 H35 3.1940 no . . C33 H37 3.1656 no . . C34 H25 2.9020 no . . C34 H38 3.2571 no . . C35 H37 3.2420 no . . C36 H34 3.2383 no . . C36 H38 3.1745 no . . C37 H35 3.2461 no . . C38 H34 3.2626 no . . H5 H12 2.9185 no . . H5 H14 2.8321 no . . H8 H9 2.3088 no . . H11 H12 2.3907 no . . H14 H15 2.3388 no . . H17 H18 2.3967 no . . H25 H32 2.9270 no . . H25 H34 2.8844 no . . H28 H29 2.3696 no . . H31 H32 2.3468 no . . H34 H35 2.3567 no . . H37 H38 2.2691 no . . Br10 H15 3.5234 no . 1_554 Br10 H17 3.1199 no . 2_566 Br10 H18 2.9408 no . 2_566 Br10 H38 3.4899 no . 1_554 Br16 H8 3.1900 no . 2_666 Br16 H9 3.0432 no . 2_666 Br16 H35 3.3646 no . 2_667 Br30 H17 3.2715 no . 1_664 Br30 H28 3.5415 no . 2_775 Br30 H37 3.1262 no . 2_676 Br30 H38 2.8962 no . 2_676 Br36 H28 3.1458 no . 2_776 Br36 H29 3.0171 no . 2_776 Br36 H37 3.2288 no . 2_677 F1 H31 3.1246 no . 2_676 F1 H32 3.1942 no . . F2 H25 2.4776 no . 2_676 F2 H31 3.3419 no . . F2 H32 3.5141 no . 2_676 F3 H3 3.2541 no . 2_576 F3 H25 2.8637 no . 1_455 F3 H34 3.2349 no . 1_455 F4 H3 2.8993 no . 2_576 F4 H25 3.3104 no . 2_676 F4 H35 2.9578 no . 2_676 F21 H11 3.1541 no . 2_666 F21 H12 3.2593 no . 1_655 F22 H5 2.4785 no . 2_666 F22 H11 3.2781 no . 1_655 F23 H5 2.8251 no . . F23 H14 3.2001 no . . F23 H23 3.2587 no . 2_666 F24 H5 3.2652 no . 2_666 F24 H14 3.5868 no . 2_666 F24 H15 2.8508 no . 2_666 F24 H23 2.9276 no . 2_666 O1 H31 3.2836 no . . O1 H32 3.1615 no . . O4 H34 3.0365 no . 1_455 O4 H35 2.9010 no . 1_455 O21 H11 3.2643 no . 1_655 O21 H12 3.2520 no . 1_655 O24 H14 3.0366 no . . O24 H15 3.0299 no . . C2 H25 3.5140 no . 2_676 C3 H25 3.5906 no . 2_676 C3 H35 3.4964 no . 1_455 C4 H34 3.4574 no . 1_455 C4 H35 3.5679 no . 1_455 C7 H23 3.2952 no . 2_666 C8 H23 3.2805 no . 2_666 C9 H15 3.2225 no . 2_666 C9 H23 3.2696 no . 2_666 C9 H37 3.2718 no . 1_554 C10 H23 3.2532 no . 2_666 C11 H17 3.4334 no . 2_566 C11 H23 3.3019 no . 2_666 C11 H28 3.3817 no . 1_455 C12 H23 3.3008 no . 2_666 C12 H28 3.1730 no . 1_455 C13 H34 3.5984 no . 1_455 C14 H38 3.1690 no . . C17 H11 3.1562 no . 2_566 C18 H11 3.4079 no . 2_566 C18 H17 3.5138 no . 2_567 C18 H34 3.2516 no . 1_455 C22 H5 3.4770 no . 2_666 C23 H5 3.5942 no . 2_666 C24 H14 3.4822 no . . C27 H3 3.1610 no . 2_676 C28 H3 3.0909 no . 2_676 C29 H3 3.0951 no . 2_676 C29 H29 3.0673 no . 2_775 C29 H35 3.1819 no . 2_776 C30 H3 3.2369 no . 2_676 C30 H29 3.5528 no . 2_775 C31 H3 3.2267 no . 2_676 C31 H8 3.3993 no . . C31 H37 3.4906 no . 2_676 C32 H3 3.1989 no . 2_676 C32 H8 3.2016 no . . C34 H18 3.0854 no . 1_655 C35 H29 3.5146 no . 2_776 C36 H9 3.4132 no . 1_556 C37 H9 3.0232 no . 1_556 C37 H31 3.1646 no . 2_676 C38 H9 3.2921 no . 1_556 C38 H14 3.3366 no . . C38 H31 3.3422 no . 2_676 H3 F3 3.2541 no . 2_576 H3 F4 2.8993 no . 2_576 H3 C27 3.1610 no . 2_676 H3 C28 3.0909 no . 2_676 H3 C29 3.0951 no . 2_676 H3 C30 3.2369 no . 2_676 H3 C31 3.2267 no . 2_676 H3 C32 3.1989 no . 2_676 H3 H25 3.2461 no . 2_676 H3 H28 3.5648 no . 2_676 H3 H29 3.5656 no . 2_676 H3 H35 3.0255 no . 1_455 H5 F22 2.4785 no . 2_666 H5 F23 2.8251 no . . H5 F24 3.2652 no . 2_666 H5 C22 3.4770 no . 2_666 H5 C23 3.5942 no . 2_666 H5 H23 3.2169 no . 2_666 H8 Br16 3.1900 no . 2_666 H8 C31 3.3993 no . . H8 C32 3.2016 no . . H8 H31 3.3051 no . . H8 H32 3.0395 no . . H9 Br16 3.0432 no . 2_666 H9 C36 3.4132 no . 1_554 H9 C37 3.0232 no . 1_554 H9 C38 3.2921 no . 1_554 H9 H15 2.8465 no . 2_666 H9 H37 3.0931 no . 1_554 H9 H38 3.5958 no . 1_554 H11 F21 3.1541 no . 2_666 H11 F22 3.2781 no . 1_455 H11 O21 3.2643 no . 1_455 H11 C17 3.1562 no . 2_566 H11 C18 3.4079 no . 2_566 H11 H17 2.7505 no . 2_566 H11 H18 3.2308 no . 2_566 H11 H28 3.3106 no . 1_455 H12 F21 3.2593 no . 1_455 H12 O21 3.2520 no . 1_455 H12 H28 2.9991 no . 1_455 H14 F23 3.2001 no . . H14 F24 3.5868 no . 2_666 H14 O24 3.0366 no . . H14 C24 3.4822 no . . H14 C38 3.3366 no . . H14 H38 2.5481 no . . H15 Br10 3.5234 no . 1_556 H15 F24 2.8508 no . 2_666 H15 O24 3.0299 no . . H15 C9 3.2225 no . 2_666 H15 H9 2.8465 no . 2_666 H15 H23 3.0859 no . . H17 Br10 3.1199 no . 2_566 H17 Br30 3.2715 no . 1_446 H17 C11 3.4334 no . 2_566 H17 C18 3.5138 no . 2_567 H17 H11 2.7505 no . 2_566 H18 Br10 2.9408 no . 2_566 H18 C34 3.0854 no . 1_455 H18 H11 3.2308 no . 2_566 H18 H34 2.4727 no . 1_455 H18 H35 3.4762 no . 1_455 H23 F23 3.2587 no . 2_666 H23 F24 2.9276 no . 2_666 H23 C7 3.2952 no . 2_666 H23 C8 3.2805 no . 2_666 H23 C9 3.2696 no . 2_666 H23 C10 3.2532 no . 2_666 H23 C11 3.3019 no . 2_666 H23 C12 3.3008 no . 2_666 H23 H5 3.2169 no . 2_666 H23 H15 3.0859 no . . H25 F2 2.4776 no . 2_676 H25 F3 2.8637 no . 1_655 H25 F4 3.3104 no . 2_676 H25 C2 3.5140 no . 2_676 H25 C3 3.5906 no . 2_676 H25 H3 3.2461 no . 2_676 H28 Br30 3.5415 no . 2_775 H28 Br36 3.1458 no . 2_776 H28 C11 3.3817 no . 1_655 H28 C12 3.1730 no . 1_655 H28 H3 3.5648 no . 2_676 H28 H11 3.3106 no . 1_655 H28 H12 2.9991 no . 1_655 H29 Br36 3.0171 no . 2_776 H29 C29 3.0673 no . 2_775 H29 C30 3.5528 no . 2_775 H29 C35 3.5146 no . 2_776 H29 H3 3.5656 no . 2_676 H29 H29 2.8766 no . 2_775 H29 H35 2.7463 no . 2_776 H31 F1 3.1246 no . 2_676 H31 F2 3.3419 no . . H31 O1 3.2836 no . . H31 C37 3.1646 no . 2_676 H31 C38 3.3422 no . 2_676 H31 H8 3.3051 no . . H31 H37 2.7962 no . 2_676 H31 H38 3.0960 no . 2_676 H32 F1 3.1942 no . . H32 F2 3.5141 no . 2_676 H32 O1 3.1615 no . . H32 H8 3.0395 no . . H34 F3 3.2349 no . 1_655 H34 O4 3.0365 no . 1_655 H34 C4 3.4574 no . 1_655 H34 C13 3.5984 no . 1_655 H34 C18 3.2516 no . 1_655 H34 H18 2.4727 no . 1_655 H35 Br16 3.3646 no . 2_667 H35 F4 2.9578 no . 2_676 H35 O4 2.9010 no . 1_655 H35 C3 3.4964 no . 1_655 H35 C4 3.5679 no . 1_655 H35 C29 3.1819 no . 2_776 H35 H3 3.0255 no . 1_655 H35 H18 3.4762 no . 1_655 H35 H29 2.7463 no . 2_776 H37 Br30 3.1262 no . 2_676 H37 Br36 3.2288 no . 2_677 H37 C9 3.2718 no . 1_556 H37 C31 3.4906 no . 2_676 H37 H9 3.0931 no . 1_556 H37 H31 2.7962 no . 2_676 H38 Br10 3.4899 no . 1_556 H38 Br30 2.8962 no . 2_676 H38 C14 3.1690 no . . H38 H9 3.5958 no . 1_556 H38 H14 2.5481 no . . H38 H31 3.0960 no . 2_676 #============================================================================== #============================================================================== # 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 #==============================================================================