# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Fumio Toda' _publ_contact_author_address ; Department of Chemistry Okayama University of Science Faculty of Science Ridai-cho 1-1 Okayama 700-0005 JAPAN ; _publ_contact_author_email toda@chem.ous.ac.jp _publ_contact_author_fax ' 81-86-256-9604 ' _publ_contact_author_phone ' 81-86-256-9604 ' _publ_contact_letter ; ? ; _publ_requested_category ' CM' _publ_section_title ; Isolation of equatorial conformers of chloro- and bromocyclohexane in a pure state as inclusion complexes with a host compound ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; loop_ _publ_author_name 'Fumio Toda' 'Shinya Hirano' 'Shinji Toyota' #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_hirano_b _database_code_depnum_ccdc_archive 'CCDC 235182' _audit_creation_date 'Fri Oct 31 17:46:57 2003' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C40 H41 Cl F4 O4 ' _chemical_formula_moiety 'C34 H30 F4 O4, C6 H11 Cl ' _chemical_formula_weight 697.21 _chemical_melting_point 227.5-228.0 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 10.2812(4) _cell_length_b 12.5651(5) _cell_length_c 13.8054(8) _cell_angle_alpha 90.791(1) _cell_angle_beta 89.982(1) _cell_angle_gamma 107.375(4) _cell_volume 1701.9(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9507 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 93.2 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.908 _exptl_absorpt_correction_T_max 0.991 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 11124 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.8715 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.8715 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). 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 6791 _reflns_number_gt 5214 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.2056 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 6791 _refine_ls_number_parameters 442 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.16000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0002 _refine_diff_density_max 1.97 _refine_diff_density_min -0.77 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Cl Cl 0.148 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; F F 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl(1) Cl 0.16203(8) 0.57849(6) 0.15676(5) 0.0286(2) Uani 1.00 d . . . F(1) F -0.0610(2) -0.0658(2) 0.3751(1) 0.0310(5) Uani 1.00 d . . . F(2) F 0.7190(2) -0.3302(1) 0.4029(1) 0.0304(5) Uani 1.00 d . . . F(3) F 0.6508(2) 0.5573(1) 0.0728(1) 0.0307(5) Uani 1.00 d . . . F(4) F 1.2869(2) 0.1684(1) -0.0142(1) 0.0238(4) Uani 1.00 d . . . O(1) O 0.4399(2) -0.0559(1) 0.1371(1) 0.0142(4) Uani 1.00 d . . . O(2) O 0.6603(2) 0.0554(1) 0.0445(1) 0.0120(4) Uani 1.00 d . . . O(3) O 0.5987(2) 0.1122(1) 0.3480(1) 0.0128(4) Uani 1.00 d . . . O(4) O 0.8028(2) 0.1798(1) 0.2709(1) 0.0122(4) Uani 1.00 d . . . C(1) C 0.3286(2) -0.0375(2) 0.2819(2) 0.0120(5) Uani 1.00 d . . . C(2) C 0.3002(2) 0.0518(2) 0.3294(2) 0.0141(6) Uani 1.00 d . . . C(3) C 0.1688(3) 0.0418(2) 0.3624(2) 0.0192(6) Uani 1.00 d . . . C(4) C 0.0677(3) -0.0568(2) 0.3446(2) 0.0200(6) Uani 1.00 d . . . C(5) C 0.0920(3) -0.1467(2) 0.2986(2) 0.0202(6) Uani 1.00 d . . . C(6) C 0.2234(3) -0.1366(2) 0.2676(2) 0.0167(6) Uani 1.00 d . . . C(7) C 0.5258(2) -0.1194(2) 0.2832(2) 0.0128(5) Uani 1.00 d . . . C(8) C 0.5753(3) -0.1893(2) 0.2244(2) 0.0167(6) Uani 1.00 d . . . C(9) C 0.6394(3) -0.2617(2) 0.2643(2) 0.0195(6) Uani 1.00 d . . . C(10) C 0.6529(3) -0.2620(2) 0.3635(2) 0.0197(6) Uani 1.00 d . . . C(11) C 0.6013(3) -0.1975(2) 0.4245(2) 0.0182(6) Uani 1.00 d . . . C(12) C 0.5372(3) -0.1255(2) 0.3836(2) 0.0145(6) Uani 1.00 d . . . C(13) C 0.4672(2) -0.0323(2) 0.2383(2) 0.0106(5) Uani 1.00 d . . . C(14) C 0.5727(2) 0.0860(2) 0.2472(2) 0.0106(5) Uani 1.00 d . . . C(15) C 0.7255(2) 0.2535(2) 0.0905(2) 0.0114(5) Uani 1.00 d . . . C(16) C 0.6011(3) 0.2596(2) 0.0548(2) 0.0147(6) Uani 1.00 d . . . C(17) C 0.5754(3) 0.3620(2) 0.0480(2) 0.0190(7) Uani 1.00 d . . . C(18) C 0.6755(3) 0.4562(2) 0.0775(2) 0.0205(7) Uani 1.00 d . . . C(19) C 0.7995(3) 0.4541(2) 0.1123(2) 0.0189(6) Uani 1.00 d . . . C(20) C 0.8245(3) 0.3519(2) 0.1181(2) 0.0147(6) Uani 1.00 d . . . C(21) C 0.8979(2) 0.1475(2) 0.0752(2) 0.0104(5) Uani 1.00 d . . . C(22) C 0.9467(3) 0.1946(2) -0.0133(2) 0.0144(6) Uani 1.00 d . . . C(23) C 1.0766(3) 0.2005(2) -0.0448(2) 0.0175(6) Uani 1.00 d . . . C(24) C 1.1576(3) 0.1587(2) 0.0142(2) 0.0154(6) Uani 1.00 d . . . C(25) C 1.1128(3) 0.1087(2) 0.1009(2) 0.0182(6) Uani 1.00 d . . . C(26) C 0.9816(3) 0.1043(2) 0.1316(2) 0.0148(6) Uani 1.00 d . . . C(27) C 0.7515(2) 0.1412(2) 0.1028(2) 0.0101(5) Uani 1.00 d . . . C(28) C 0.7169(2) 0.0987(2) 0.2076(2) 0.0103(5) Uani 1.00 d . . . C(29) C 0.7314(2) 0.1885(2) 0.3589(2) 0.0104(5) Uani 1.00 d . . . C(30) C 0.8044(3) 0.1543(2) 0.4426(2) 0.0151(6) Uani 1.00 d . . . C(31) C 0.9491(3) 0.2358(3) 0.4519(2) 0.0223(7) Uani 1.00 d . . . C(32) C 0.9438(3) 0.3544(3) 0.4670(2) 0.0293(7) Uani 1.00 d . . . C(33) C 0.8677(3) 0.3901(2) 0.3842(2) 0.0254(7) Uani 1.00 d . . . C(34) C 0.7256(3) 0.3073(2) 0.3707(2) 0.0194(6) Uani 1.00 d . . . C(35) C 0.2803(4) 0.5188(3) 0.2179(3) 0.040(1) Uani 1.00 d . . . C(36) C 0.2527(5) 0.4022(3) 0.1933(3) 0.050(1) Uani 1.00 d . . . C(37) C 0.3424(4) 0.3472(3) 0.2491(3) 0.0347(9) Uani 1.00 d . . . C(38) C 0.3426(4) 0.3691(3) 0.3546(3) 0.043(1) Uani 1.00 d . . . C(39) C 0.3723(4) 0.4907(3) 0.3802(3) 0.046(1) Uani 1.00 d . . . C(40) C 0.2869(3) 0.5497(2) 0.3239(2) 0.0245(7) Uani 1.00 d . . . H(1) H 0.5209 -0.0246 0.1020 0.0357 Uiso 1.00 calc . . . H(2) H 0.3702 0.1201 0.3401 0.0163 Uiso 1.00 calc . . . H(3) H 0.1495 0.1011 0.3965 0.0239 Uiso 1.00 calc . . . H(4) H 0.0211 -0.2140 0.2886 0.0242 Uiso 1.00 calc . . . H(5) H 0.2412 -0.1980 0.2357 0.0195 Uiso 1.00 calc . . . H(6) H 0.5663 -0.1873 0.1564 0.0195 Uiso 1.00 calc . . . H(7) H 0.6729 -0.3096 0.2246 0.0230 Uiso 1.00 calc . . . H(8) H 0.6091 -0.2010 0.4924 0.0235 Uiso 1.00 calc . . . H(9) H 0.4999 -0.0808 0.4249 0.0175 Uiso 1.00 calc . . . H(10) H 0.5357 0.1398 0.2181 0.0135 Uiso 1.00 calc . . . H(11) H 0.6602 0.0718 -0.0173 0.0357 Uiso 1.00 calc . . . H(12) H 0.5341 0.1935 0.0344 0.0174 Uiso 1.00 calc . . . H(13) H 0.4906 0.3664 0.0248 0.0228 Uiso 1.00 calc . . . H(14) H 0.8674 0.5207 0.1327 0.0220 Uiso 1.00 calc . . . H(15) H 0.9104 0.3488 0.1408 0.0168 Uiso 1.00 calc . . . H(16) H 0.8902 0.2236 -0.0527 0.0171 Uiso 1.00 calc . . . H(17) H 1.1094 0.2333 -0.1048 0.0202 Uiso 1.00 calc . . . H(18) H 1.1696 0.0779 0.1389 0.0228 Uiso 1.00 calc . . . H(19) H 0.9494 0.0709 0.1918 0.0184 Uiso 1.00 calc . . . H(20) H 0.7360 0.0296 0.2139 0.0126 Uiso 1.00 calc . . . H(21) H 0.8098 0.0805 0.4309 0.0177 Uiso 1.00 calc . . . H(22) H 0.7561 0.1551 0.5010 0.0177 Uiso 1.00 calc . . . H(23) H 0.9987 0.2315 0.3944 0.0261 Uiso 1.00 calc . . . H(24) H 0.9942 0.2151 0.5056 0.0261 Uiso 1.00 calc . . . H(25) H 1.0350 0.4036 0.4701 0.0351 Uiso 1.00 calc . . . H(26) H 0.8992 0.3592 0.5262 0.0351 Uiso 1.00 calc . . . H(27) H 0.9178 0.3933 0.3252 0.0302 Uiso 1.00 calc . . . H(28) H 0.8598 0.4626 0.3978 0.0302 Uiso 1.00 calc . . . H(29) H 0.6718 0.3121 0.4259 0.0244 Uiso 1.00 calc . . . H(30) H 0.6837 0.3266 0.3145 0.0244 Uiso 1.00 calc . . . H(31) H 0.3662 0.5547 0.1925 0.0574 Uiso 1.00 calc . . . H(32) H 0.1599 0.3639 0.2056 0.0633 Uiso 1.00 calc . . . H(33) H 0.2692 0.3964 0.1250 0.0633 Uiso 1.00 calc . . . H(34) H 0.3108 0.2686 0.2381 0.0423 Uiso 1.00 calc . . . H(35) H 0.4341 0.3745 0.2253 0.0423 Uiso 1.00 calc . . . H(36) H 0.4136 0.3437 0.3840 0.0591 Uiso 1.00 calc . . . H(37) H 0.2586 0.3300 0.3808 0.0591 Uiso 1.00 calc . . . H(38) H 0.4669 0.5285 0.3693 0.0544 Uiso 1.00 calc . . . H(39) H 0.3554 0.4975 0.4485 0.0544 Uiso 1.00 calc . . . H(40) H 0.3272 0.6287 0.3306 0.0302 Uiso 1.00 calc . . . H(41) H 0.1978 0.5300 0.3504 0.0302 Uiso 1.00 calc . . . 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 Cl(1) 0.0333(4) 0.0232(4) 0.0313(4) 0.0112(3) -0.0094(3) 0.0014(3) F(1) 0.0102(8) 0.039(1) 0.044(1) 0.0064(7) 0.0066(7) 0.0046(8) F(2) 0.030(1) 0.0278(9) 0.040(1) 0.0182(7) -0.0060(8) 0.0064(7) F(3) 0.040(1) 0.0200(8) 0.040(1) 0.0202(8) -0.0096(8) -0.0010(7) F(4) 0.0106(8) 0.0337(9) 0.0278(9) 0.0078(6) 0.0076(6) 0.0017(7) O(1) 0.0125(8) 0.0190(9) 0.0053(7) -0.0039(7) -0.0015(6) -0.0007(6) O(2) 0.0112(8) 0.0145(8) 0.0072(7) -0.0010(6) -0.0022(6) -0.0009(6) O(3) 0.0100(8) 0.0164(8) 0.0075(8) -0.0025(6) -0.0009(6) -0.0035(6) O(4) 0.0107(8) 0.0158(8) 0.0062(7) -0.0016(6) -0.0003(6) -0.0039(6) C(1) 0.009(1) 0.017(1) 0.009(1) 0.0021(9) -0.0024(8) 0.0018(8) C(2) 0.010(1) 0.017(1) 0.015(1) 0.0029(9) -0.0015(9) 0.0014(9) C(3) 0.016(1) 0.024(1) 0.021(1) 0.010(1) 0.0020(10) 0.003(1) C(4) 0.008(1) 0.030(1) 0.021(1) 0.004(1) 0.0019(9) 0.008(1) C(5) 0.013(1) 0.023(1) 0.020(1) -0.0031(10) -0.0018(9) 0.003(1) C(6) 0.013(1) 0.019(1) 0.015(1) -0.0005(9) -0.0012(9) 0.0000(9) C(7) 0.012(1) 0.012(1) 0.012(1) -0.0011(9) 0.0001(8) 0.0005(8) C(8) 0.017(1) 0.017(1) 0.014(1) 0.0025(9) 0.0036(9) 0.0016(9) C(9) 0.019(1) 0.015(1) 0.024(1) 0.0047(10) 0.005(1) -0.0006(10) C(10) 0.013(1) 0.018(1) 0.029(1) 0.0049(10) -0.0027(10) 0.006(1) C(11) 0.018(1) 0.019(1) 0.016(1) 0.0028(10) -0.0055(9) 0.0023(9) C(12) 0.015(1) 0.016(1) 0.012(1) 0.0045(9) -0.0004(9) -0.0002(9) C(13) 0.011(1) 0.012(1) 0.0053(10) -0.0017(8) -0.0009(8) 0.0001(8) C(14) 0.012(1) 0.011(1) 0.0062(10) 0.0006(8) -0.0006(8) -0.0009(8) C(15) 0.011(1) 0.015(1) 0.008(1) 0.0045(9) 0.0024(8) 0.0016(8) C(16) 0.012(1) 0.019(1) 0.014(1) 0.0070(9) -0.0005(9) 0.0014(9) C(17) 0.018(1) 0.024(1) 0.018(1) 0.012(1) -0.0020(10) 0.0033(10) C(18) 0.028(2) 0.016(1) 0.022(1) 0.013(1) 0.000(1) 0.0020(10) C(19) 0.022(1) 0.014(1) 0.022(1) 0.0074(10) -0.0020(10) -0.0017(10) C(20) 0.013(1) 0.015(1) 0.016(1) 0.0052(9) -0.0011(9) 0.0005(9) C(21) 0.011(1) 0.009(1) 0.011(1) 0.0020(8) 0.0002(8) -0.0025(8) C(22) 0.013(1) 0.018(1) 0.013(1) 0.0064(9) 0.0003(9) 0.0022(9) C(23) 0.017(1) 0.021(1) 0.014(1) 0.0047(10) 0.0035(9) 0.0011(9) C(24) 0.011(1) 0.016(1) 0.019(1) 0.0027(9) 0.0042(9) -0.0024(9) C(25) 0.013(1) 0.024(1) 0.019(1) 0.0083(10) 0.0009(9) 0.0010(10) C(26) 0.015(1) 0.018(1) 0.013(1) 0.0064(9) 0.0019(9) 0.0027(9) C(27) 0.010(1) 0.010(1) 0.009(1) 0.0008(8) -0.0017(8) -0.0010(8) C(28) 0.009(1) 0.010(1) 0.009(1) -0.0001(8) -0.0022(8) -0.0016(8) C(29) 0.007(1) 0.013(1) 0.009(1) 0.0004(8) -0.0006(8) -0.0027(8) C(30) 0.012(1) 0.022(1) 0.010(1) 0.0023(9) -0.0013(8) 0.0013(9) C(31) 0.013(1) 0.037(2) 0.011(1) 0.000(1) -0.0023(9) 0.000(1) C(32) 0.021(1) 0.034(2) 0.021(1) -0.010(1) 0.000(1) -0.013(1) C(33) 0.027(2) 0.014(1) 0.029(1) -0.003(1) 0.001(1) -0.009(1) C(34) 0.020(1) 0.015(1) 0.022(1) 0.0037(10) 0.0019(10) -0.0035(10) C(35) 0.048(2) 0.042(2) 0.039(2) 0.027(2) -0.016(2) -0.005(1) C(36) 0.092(3) 0.043(2) 0.029(2) 0.044(2) -0.022(2) -0.011(1) C(37) 0.047(2) 0.026(2) 0.039(2) 0.022(1) 0.005(1) 0.005(1) C(38) 0.041(2) 0.048(2) 0.044(2) 0.017(2) -0.008(2) 0.009(2) C(39) 0.066(3) 0.028(2) 0.037(2) 0.004(2) -0.030(2) 0.005(1) C(40) 0.032(2) 0.022(1) 0.021(1) 0.011(1) -0.001(1) 0.000(1) #------------------------------------------------------------------------------ _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl(1) C(35) 1.821(3) . . yes F(1) C(4) 1.361(3) . . yes F(2) C(10) 1.361(3) . . yes F(3) C(18) 1.370(3) . . yes F(4) C(24) 1.356(3) . . yes O(1) C(13) 1.435(3) . . yes O(2) C(27) 1.436(3) . . yes O(3) C(14) 1.432(3) . . yes O(3) C(29) 1.420(3) . . yes O(4) C(28) 1.422(3) . . yes O(4) C(29) 1.439(3) . . yes C(1) C(2) 1.396(3) . . yes C(1) C(6) 1.397(3) . . yes C(1) C(13) 1.531(3) . . yes C(2) C(3) 1.395(3) . . yes C(3) C(4) 1.378(4) . . yes C(4) C(5) 1.375(4) . . yes C(5) C(6) 1.386(4) . . yes C(7) C(8) 1.391(3) . . yes C(7) C(12) 1.395(3) . . yes C(7) C(13) 1.536(3) . . yes C(8) C(9) 1.393(4) . . yes C(9) C(10) 1.375(4) . . yes C(10) C(11) 1.373(4) . . yes C(11) C(12) 1.393(4) . . yes C(13) C(14) 1.559(3) . . yes C(14) C(28) 1.543(3) . . yes C(15) C(16) 1.394(4) . . yes C(15) C(20) 1.394(3) . . yes C(15) C(27) 1.525(3) . . yes C(16) C(17) 1.393(3) . . yes C(17) C(18) 1.373(4) . . yes C(18) C(19) 1.370(4) . . yes C(19) C(20) 1.387(3) . . yes C(21) C(22) 1.391(3) . . yes C(21) C(26) 1.390(3) . . yes C(21) C(27) 1.532(3) . . yes C(22) C(23) 1.386(3) . . yes C(23) C(24) 1.382(4) . . yes C(24) C(25) 1.373(4) . . yes C(25) C(26) 1.400(3) . . yes C(27) C(28) 1.553(3) . . yes C(29) C(30) 1.513(3) . . yes C(29) C(34) 1.518(3) . . yes C(30) C(31) 1.537(3) . . yes C(31) C(32) 1.519(4) . . yes C(32) C(33) 1.531(4) . . yes C(33) C(34) 1.529(4) . . yes C(35) C(36) 1.443(5) . . yes C(35) C(40) 1.506(4) . . yes C(36) C(37) 1.522(5) . . yes C(37) C(38) 1.479(5) . . yes C(38) C(39) 1.503(5) . . yes C(39) C(40) 1.526(4) . . yes #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(14) O(3) C(29) 109.0(2) . . . yes C(28) O(4) C(29) 110.0(2) . . . yes C(2) C(1) C(6) 118.9(2) . . . yes C(2) C(1) C(13) 124.2(2) . . . yes C(6) C(1) C(13) 116.8(2) . . . yes C(1) C(2) C(3) 120.5(2) . . . yes C(2) C(3) C(4) 118.5(2) . . . yes F(1) C(4) C(3) 118.5(2) . . . yes F(1) C(4) C(5) 118.8(2) . . . yes C(3) C(4) C(5) 122.7(2) . . . yes C(4) C(5) C(6) 118.4(2) . . . yes C(1) C(6) C(5) 121.0(2) . . . yes C(8) C(7) C(12) 118.9(2) . . . yes C(8) C(7) C(13) 120.4(2) . . . yes C(12) C(7) C(13) 120.5(2) . . . yes C(7) C(8) C(9) 120.9(2) . . . yes C(8) C(9) C(10) 118.2(2) . . . yes F(2) C(10) C(9) 118.5(2) . . . yes F(2) C(10) C(11) 118.5(2) . . . yes C(9) C(10) C(11) 123.0(2) . . . yes C(10) C(11) C(12) 118.2(2) . . . yes C(7) C(12) C(11) 120.8(2) . . . yes O(1) C(13) C(1) 104.5(2) . . . yes O(1) C(13) C(7) 110.4(2) . . . yes O(1) C(13) C(14) 107.4(2) . . . yes C(1) C(13) C(7) 111.4(2) . . . yes C(1) C(13) C(14) 112.9(2) . . . yes C(7) C(13) C(14) 110.0(2) . . . yes O(3) C(14) C(13) 108.2(2) . . . yes O(3) C(14) C(28) 102.3(2) . . . yes C(13) C(14) C(28) 116.7(2) . . . yes C(16) C(15) C(20) 118.9(2) . . . yes C(16) C(15) C(27) 120.8(2) . . . yes C(20) C(15) C(27) 120.3(2) . . . yes C(15) C(16) C(17) 120.6(2) . . . yes C(16) C(17) C(18) 118.2(3) . . . yes F(3) C(18) C(17) 118.9(3) . . . yes F(3) C(18) C(19) 118.0(2) . . . yes C(17) C(18) C(19) 123.1(2) . . . yes C(18) C(19) C(20) 118.3(2) . . . yes C(15) C(20) C(19) 120.9(2) . . . yes C(22) C(21) C(26) 118.6(2) . . . yes C(22) C(21) C(27) 117.8(2) . . . yes C(26) C(21) C(27) 123.5(2) . . . yes C(21) C(22) C(23) 121.4(2) . . . yes C(22) C(23) C(24) 118.2(2) . . . yes F(4) C(24) C(23) 118.7(2) . . . yes F(4) C(24) C(25) 118.8(2) . . . yes C(23) C(24) C(25) 122.6(2) . . . yes C(24) C(25) C(26) 118.2(2) . . . yes C(21) C(26) C(25) 121.0(2) . . . yes O(2) C(27) C(15) 111.7(2) . . . yes O(2) C(27) C(21) 108.2(2) . . . yes O(2) C(27) C(28) 103.1(2) . . . yes C(15) C(27) C(21) 111.3(2) . . . yes C(15) C(27) C(28) 110.5(2) . . . yes C(21) C(27) C(28) 111.8(2) . . . yes O(4) C(28) C(14) 103.4(2) . . . yes O(4) C(28) C(27) 106.9(2) . . . yes C(14) C(28) C(27) 118.9(2) . . . yes O(3) C(29) O(4) 106.0(2) . . . yes O(3) C(29) C(30) 109.9(2) . . . yes O(3) C(29) C(34) 111.2(2) . . . yes O(4) C(29) C(30) 108.6(2) . . . yes O(4) C(29) C(34) 108.9(2) . . . yes C(30) C(29) C(34) 112.1(2) . . . yes C(29) C(30) C(31) 109.4(2) . . . yes C(30) C(31) C(32) 110.6(2) . . . yes C(31) C(32) C(33) 111.5(2) . . . yes C(32) C(33) C(34) 110.7(2) . . . yes C(29) C(34) C(33) 111.7(2) . . . yes Cl(1) C(35) C(36) 111.2(3) . . . yes Cl(1) C(35) C(40) 109.4(2) . . . yes C(36) C(35) C(40) 117.1(3) . . . yes C(35) C(36) C(37) 112.7(3) . . . yes C(36) C(37) C(38) 112.8(3) . . . yes C(37) C(38) C(39) 113.3(3) . . . yes C(38) C(39) C(40) 114.1(3) . . . yes C(35) C(40) C(39) 111.3(3) . . . yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl(1) C(35) C(36) C(37) -175.5(3) . . . . yes Cl(1) C(35) C(40) C(39) 173.6(2) . . . . yes F(1) C(4) C(3) C(2) -178.8(2) . . . . yes F(1) C(4) C(5) C(6) 179.9(2) . . . . yes F(2) C(10) C(9) C(8) -178.1(2) . . . . yes F(2) C(10) C(11) C(12) 178.2(2) . . . . yes F(3) C(18) C(17) C(16) -178.9(2) . . . . yes F(3) C(18) C(19) C(20) 179.4(2) . . . . yes F(4) C(24) C(23) C(22) -177.3(2) . . . . yes F(4) C(24) C(25) C(26) 176.9(2) . . . . yes O(1) C(13) C(1) C(2) -119.6(2) . . . . yes O(1) C(13) C(1) C(6) 56.6(3) . . . . yes O(1) C(13) C(7) C(8) 15.3(3) . . . . yes O(1) C(13) C(7) C(12) -168.4(2) . . . . yes O(1) C(13) C(14) O(3) 178.6(2) . . . . yes O(1) C(13) C(14) C(28) -66.9(2) . . . . yes O(2) C(27) C(15) C(16) 20.4(3) . . . . yes O(2) C(27) C(15) C(20) -161.9(2) . . . . yes O(2) C(27) C(21) C(22) 73.3(2) . . . . yes O(2) C(27) C(21) C(26) -103.7(2) . . . . yes O(2) C(27) C(28) O(4) -179.6(2) . . . . yes O(2) C(27) C(28) C(14) -63.3(2) . . . . yes O(3) C(14) C(13) C(1) 63.9(2) . . . . yes O(3) C(14) C(13) C(7) -61.2(2) . . . . yes O(3) C(14) C(28) O(4) -28.8(2) . . . . yes O(3) C(14) C(28) C(27) -146.9(2) . . . . yes O(3) C(29) O(4) C(28) -0.9(2) . . . . yes O(3) C(29) C(30) C(31) 178.5(2) . . . . yes O(3) C(29) C(34) C(33) 179.1(2) . . . . yes O(4) C(28) C(14) C(13) -146.6(2) . . . . yes O(4) C(28) C(27) C(15) -60.1(2) . . . . yes O(4) C(28) C(27) C(21) 64.4(2) . . . . yes O(4) C(29) O(3) C(14) -19.1(2) . . . . yes O(4) C(29) C(30) C(31) 63.0(2) . . . . yes O(4) C(29) C(34) C(33) -64.5(3) . . . . yes C(1) C(2) C(3) C(4) -1.8(4) . . . . yes C(1) C(6) C(5) C(4) -0.4(4) . . . . yes C(1) C(13) C(7) C(8) 130.9(2) . . . . yes C(1) C(13) C(7) C(12) -52.7(3) . . . . yes C(1) C(13) C(14) C(28) 178.4(2) . . . . yes C(2) C(1) C(6) C(5) 0.8(4) . . . . yes C(2) C(1) C(13) C(7) 121.2(2) . . . . yes C(2) C(1) C(13) C(14) -3.2(3) . . . . yes C(2) C(3) C(4) C(5) 2.2(4) . . . . yes C(3) C(2) C(1) C(6) 0.3(4) . . . . yes C(3) C(2) C(1) C(13) 176.4(2) . . . . yes C(3) C(4) C(5) C(6) -1.1(4) . . . . yes C(5) C(6) C(1) C(13) -175.6(2) . . . . yes C(6) C(1) C(13) C(7) -62.7(3) . . . . yes C(6) C(1) C(13) C(14) 173.0(2) . . . . yes C(7) C(8) C(9) C(10) -0.2(4) . . . . yes C(7) C(12) C(11) C(10) 0.0(4) . . . . yes C(7) C(13) C(14) C(28) 53.3(2) . . . . yes C(8) C(7) C(12) C(11) 2.2(4) . . . . yes C(8) C(7) C(13) C(14) -103.1(2) . . . . yes C(8) C(9) C(10) C(11) 2.6(4) . . . . yes C(9) C(8) C(7) C(12) -2.1(4) . . . . yes C(9) C(8) C(7) C(13) 174.3(2) . . . . yes C(9) C(10) C(11) C(12) -2.5(4) . . . . yes C(11) C(12) C(7) C(13) -174.2(2) . . . . yes C(12) C(7) C(13) C(14) 73.2(3) . . . . yes C(13) C(14) O(3) C(29) 153.3(2) . . . . yes C(13) C(14) C(28) C(27) 95.3(2) . . . . yes C(14) O(3) C(29) C(30) -136.2(2) . . . . yes C(14) O(3) C(29) C(34) 99.1(2) . . . . yes C(14) C(28) O(4) C(29) 18.5(2) . . . . yes C(14) C(28) C(27) C(15) 56.2(3) . . . . yes C(14) C(28) C(27) C(21) -179.3(2) . . . . yes C(15) C(16) C(17) C(18) -0.2(4) . . . . yes C(15) C(20) C(19) C(18) -0.9(4) . . . . yes C(15) C(27) C(21) C(22) -49.8(3) . . . . yes C(15) C(27) C(21) C(26) 133.2(2) . . . . yes C(16) C(15) C(20) C(19) 1.4(4) . . . . yes C(16) C(15) C(27) C(21) 141.5(2) . . . . yes C(16) C(15) C(27) C(28) -93.7(2) . . . . yes C(16) C(17) C(18) C(19) 0.7(4) . . . . yes C(17) C(16) C(15) C(20) -0.8(4) . . . . yes C(17) C(16) C(15) C(27) 176.9(2) . . . . yes C(17) C(18) C(19) C(20) -0.2(4) . . . . yes C(19) C(20) C(15) C(27) -176.4(2) . . . . yes C(20) C(15) C(27) C(21) -40.8(3) . . . . yes C(20) C(15) C(27) C(28) 84.0(3) . . . . yes C(21) C(22) C(23) C(24) -0.3(4) . . . . yes C(21) C(26) C(25) C(24) 1.2(4) . . . . yes C(22) C(21) C(26) C(25) 0.5(4) . . . . yes C(22) C(21) C(27) C(28) -173.8(2) . . . . yes C(22) C(23) C(24) C(25) 2.2(4) . . . . yes C(23) C(22) C(21) C(26) -1.0(4) . . . . yes C(23) C(22) C(21) C(27) -178.2(2) . . . . yes C(23) C(24) C(25) C(26) -2.6(4) . . . . yes C(25) C(26) C(21) C(27) 177.6(2) . . . . yes C(26) C(21) C(27) C(28) 9.1(3) . . . . yes C(27) C(28) O(4) C(29) 144.7(2) . . . . yes C(28) O(4) C(29) C(30) 117.2(2) . . . . yes C(28) O(4) C(29) C(34) -120.6(2) . . . . yes C(28) C(14) O(3) C(29) 29.6(2) . . . . yes C(29) C(30) C(31) C(32) 58.1(3) . . . . yes C(29) C(34) C(33) C(32) -53.1(3) . . . . yes C(30) C(29) C(34) C(33) 55.6(3) . . . . yes C(30) C(31) C(32) C(33) -57.6(3) . . . . yes C(31) C(30) C(29) C(34) -57.3(3) . . . . yes C(31) C(32) C(33) C(34) 54.6(3) . . . . yes C(35) C(36) C(37) C(38) 50.2(5) . . . . yes C(35) C(40) C(39) C(38) -44.8(4) . . . . yes C(36) C(35) C(40) C(39) 45.9(5) . . . . yes C(36) C(37) C(38) C(39) -50.9(5) . . . . yes C(37) C(36) C(35) C(40) -48.7(5) . . . . yes C(37) C(38) C(39) C(40) 49.3(5) . . . . yes C(37) C(38) C(39) C(40) 49.3(5) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F(1) C(10) 3.227(3) . 1_455 ? F(1) F(2) 3.441(3) . 1_455 ? F(1) C(11) 3.443(3) . 1_455 ? F(1) C(30) 3.557(3) . 1_455 ? F(2) C(38) 3.421(4) . 2_656 ? F(2) C(39) 3.599(4) . 2_656 ? F(3) C(17) 3.267(3) . 2_665 ? F(3) F(4) 3.422(2) . 2_765 ? F(3) C(9) 3.489(3) . 1_565 ? F(3) C(23) 3.493(3) . 2_765 ? F(4) O(2) 3.042(2) . 2_755 ? F(4) C(8) 3.209(3) . 2_755 ? F(4) C(16) 3.227(3) . 1_655 ? F(4) C(17) 3.329(3) . 1_655 ? O(1) O(2) 2.711(2) . 2_655 ? O(1) C(16) 3.594(3) . 2_655 ? O(2) O(2) 3.396(3) . 2_655 ? C(4) C(30) 3.595(4) . 2_656 ? C(4) C(31) 3.595(4) . 2_656 ? C(10) C(39) 3.563(5) . 1_545 ? C(32) C(32) 3.597(6) . 2_766 ? #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_site_distance_DH _geom_hbond_site_distance_HA _geom_hbond_site_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1) O(2) . . . 0.943 1.691 2.622(2) 168.676 no O(2) H(11) O(1) . . 2_655 0.880 1.923 2.710(2) 148.040 no O(2) H(11) O(2) . . 2_655 0.880 3.224 3.397(2) 93.710 no #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_hirano _database_code_depnum_ccdc_archive 'CCDC 235183' _audit_creation_date 'Sat Jul 31 08:55:15 2004' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C40 H41 Br F4 O4 ' _chemical_formula_moiety 'C34 H30 F4 O4, C6 H11 Br' _chemical_formula_weight 741.66 _chemical_melting_point 226.5-227.0 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 10.2862(6) _cell_length_b 12.7217(8) _cell_length_c 13.8094(8) _cell_angle_alpha 91.793(3) _cell_angle_beta 89.989(4) _cell_angle_gamma 106.967(2) _cell_volume 1727.5(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9683 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 113.2 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 1.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.682 _exptl_absorpt_correction_T_max 0.778 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 9663 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.7752 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.7752 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). 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 6118 _reflns_number_gt 5360 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1635 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 6118 _refine_ls_number_parameters 442 _refine_ls_goodness_of_fit_ref 1.367 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.09500(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0003 _refine_diff_density_max 1.17 _refine_diff_density_min -0.98 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Br Br -0.290 2.459 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; F F 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br(1) Br 0.15653(3) 0.57509(3) 0.15131(2) 0.0405(1) Uani 1.00 d . . . F(1) F 0.7185(2) -0.3281(2) 0.3958(2) 0.0450(6) Uani 1.00 d . . . F(2) F -0.0617(2) -0.0645(2) 0.3748(2) 0.0433(6) Uani 1.00 d . . . F(3) F 1.2803(2) 0.1660(2) -0.0145(1) 0.0365(5) Uani 1.00 d . . . F(4) F 0.6322(2) 0.5450(2) 0.0775(2) 0.0490(6) Uani 1.00 d . . . O(1) O 0.4377(2) -0.0536(2) 0.1373(1) 0.0234(5) Uani 1.00 d . . . O(2) O 0.6584(2) 0.0531(1) 0.0463(1) 0.0200(4) Uani 1.00 d . . . O(3) O 0.5970(2) 0.1105(1) 0.3503(1) 0.0212(4) Uani 1.00 d . . . O(4) O 0.7997(2) 0.1784(1) 0.2737(1) 0.0212(4) Uani 1.00 d . . . C(1) C 0.5242(2) -0.1182(2) 0.2815(2) 0.0202(6) Uani 1.00 d . . . C(2) C 0.5372(3) -0.1241(2) 0.3815(2) 0.0243(7) Uani 1.00 d . . . C(3) C 0.6014(3) -0.1954(2) 0.4206(2) 0.0297(7) Uani 1.00 d . . . C(4) C 0.6521(3) -0.2603(2) 0.3580(2) 0.0307(7) Uani 1.00 d . . . C(5) C 0.6376(3) -0.2597(2) 0.2594(2) 0.0306(7) Uani 1.00 d . . . C(6) C 0.5723(3) -0.1876(2) 0.2215(2) 0.0254(7) Uani 1.00 d . . . C(7) C 0.3278(2) -0.0362(2) 0.2824(2) 0.0216(6) Uani 1.00 d . . . C(8) C 0.2984(3) 0.0507(2) 0.3315(2) 0.0228(6) Uani 1.00 d . . . C(9) C 0.1668(3) 0.0412(2) 0.3639(2) 0.0300(7) Uani 1.00 d . . . C(10) C 0.0674(3) -0.0550(3) 0.3445(2) 0.0304(7) Uani 1.00 d . . . C(11) C 0.0921(3) -0.1443(2) 0.2974(2) 0.0304(7) Uani 1.00 d . . . C(12) C 0.2231(3) -0.1343(2) 0.2671(2) 0.0251(7) Uani 1.00 d . . . C(13) C 0.4658(2) -0.0317(2) 0.2388(2) 0.0188(6) Uani 1.00 d . . . C(14) C 0.5699(2) 0.0854(2) 0.2497(2) 0.0185(6) Uani 1.00 d . . . C(15) C 0.8936(2) 0.1468(2) 0.0780(2) 0.0182(6) Uani 1.00 d . . . C(16) C 0.9784(3) 0.1036(2) 0.1328(2) 0.0243(7) Uani 1.00 d . . . C(17) C 1.1092(3) 0.1081(2) 0.1008(2) 0.0269(7) Uani 1.00 d . . . C(18) C 1.1519(3) 0.1577(2) 0.0159(2) 0.0253(7) Uani 1.00 d . . . C(19) C 1.0713(3) 0.2005(2) -0.0419(2) 0.0289(7) Uani 1.00 d . . . C(20) C 0.9414(3) 0.1942(2) -0.0094(2) 0.0251(7) Uani 1.00 d . . . C(21) C 0.7167(2) 0.2487(2) 0.0941(2) 0.0209(6) Uani 1.00 d . . . C(22) C 0.8128(3) 0.3466(2) 0.1244(2) 0.0243(6) Uani 1.00 d . . . C(23) C 0.7841(3) 0.4469(2) 0.1197(2) 0.0306(7) Uani 1.00 d . . . C(24) C 0.6599(3) 0.4462(2) 0.0823(2) 0.0319(8) Uani 1.00 d . . . C(25) C 0.5638(3) 0.3525(3) 0.0501(2) 0.0310(8) Uani 1.00 d . . . C(26) C 0.5926(3) 0.2527(2) 0.0565(2) 0.0246(7) Uani 1.00 d . . . C(27) C 0.7472(2) 0.1392(2) 0.1062(2) 0.0181(6) Uani 1.00 d . . . C(28) C 0.7138(2) 0.0978(2) 0.2095(2) 0.0179(6) Uani 1.00 d . . . C(29) C 0.7299(2) 0.1863(2) 0.3614(2) 0.0201(6) Uani 1.00 d . . . C(30) C 0.8041(3) 0.1516(2) 0.4445(2) 0.0263(7) Uani 1.00 d . . . C(31) C 0.9472(3) 0.2332(3) 0.4548(2) 0.0316(7) Uani 1.00 d . . . C(32) C 0.9411(3) 0.3506(3) 0.4719(3) 0.0407(9) Uani 1.00 d . . . C(33) C 0.8631(3) 0.3849(2) 0.3906(3) 0.0386(8) Uani 1.00 d . . . C(34) C 0.7214(3) 0.3030(2) 0.3762(2) 0.0305(7) Uani 1.00 d . . . C(35) C 0.2848(4) 0.5142(3) 0.2212(3) 0.045(1) Uani 1.00 d . . . C(36) C 0.2553(5) 0.3971(3) 0.1995(3) 0.055(1) Uani 1.00 d . . . C(37) C 0.3444(5) 0.3453(3) 0.2573(3) 0.053(1) Uani 1.00 d . . . C(38) C 0.3448(4) 0.3703(3) 0.3634(3) 0.053(1) Uani 1.00 d . . . C(39) C 0.3740(5) 0.4925(3) 0.3851(3) 0.055(1) Uani 1.00 d . . . C(40) C 0.2874(4) 0.5463(3) 0.3276(2) 0.0385(9) Uani 1.00 d . . . H(1) H 0.5103 -0.0339 0.1075 0.0539 Uiso 1.00 calc . . . H(2) H 0.5016 -0.0791 0.4235 0.0283 Uiso 1.00 calc . . . H(3) H 0.6103 -0.1997 0.4885 0.0345 Uiso 1.00 calc . . . H(4) H 0.6708 -0.3068 0.2182 0.0361 Uiso 1.00 calc . . . H(5) H 0.5608 -0.1862 0.1531 0.0299 Uiso 1.00 calc . . . H(6) H 0.3686 0.1177 0.3434 0.0263 Uiso 1.00 calc . . . H(7) H 0.1470 0.1002 0.3986 0.0355 Uiso 1.00 calc . . . H(8) H 0.0212 -0.2104 0.2861 0.0354 Uiso 1.00 calc . . . H(9) H 0.2424 -0.1951 0.2350 0.0293 Uiso 1.00 calc . . . H(10) H 0.5327 0.1379 0.2221 0.0217 Uiso 1.00 calc . . . H(11) H 0.6765 0.0772 -0.0083 0.0579 Uiso 1.00 calc . . . H(12) H 0.9473 0.0705 0.1923 0.0284 Uiso 1.00 calc . . . H(13) H 1.1667 0.0775 0.1373 0.0315 Uiso 1.00 calc . . . H(14) H 1.1038 0.2334 -0.1013 0.0336 Uiso 1.00 calc . . . H(15) H 0.8842 0.2228 -0.0481 0.0293 Uiso 1.00 calc . . . H(16) H 0.8983 0.3446 0.1486 0.0280 Uiso 1.00 calc . . . H(17) H 0.8483 0.5135 0.1414 0.0360 Uiso 1.00 calc . . . H(18) H 0.4798 0.3557 0.0237 0.0365 Uiso 1.00 calc . . . H(19) H 0.5271 0.1866 0.0351 0.0285 Uiso 1.00 calc . . . H(20) H 0.7343 0.0302 0.2153 0.0207 Uiso 1.00 calc . . . H(21) H 0.8109 0.0798 0.4308 0.0305 Uiso 1.00 calc . . . H(22) H 0.7556 0.1522 0.5028 0.0305 Uiso 1.00 calc . . . H(23) H 0.9927 0.2133 0.5079 0.0374 Uiso 1.00 calc . . . H(24) H 0.9964 0.2298 0.3970 0.0374 Uiso 1.00 calc . . . H(25) H 1.0311 0.3988 0.4749 0.0485 Uiso 1.00 calc . . . H(26) H 0.8970 0.3549 0.5317 0.0485 Uiso 1.00 calc . . . H(27) H 0.9123 0.3882 0.3323 0.0452 Uiso 1.00 calc . . . H(28) H 0.8535 0.4554 0.4070 0.0452 Uiso 1.00 calc . . . H(29) H 0.6683 0.3059 0.4322 0.0358 Uiso 1.00 calc . . . H(30) H 0.6792 0.3220 0.3213 0.0358 Uiso 1.00 calc . . . H(31) H 0.3717 0.5479 0.1969 0.0554 Uiso 1.00 calc . . . H(32) H 0.1627 0.3618 0.2143 0.0655 Uiso 1.00 calc . . . H(33) H 0.2698 0.3866 0.1326 0.0655 Uiso 1.00 calc . . . H(34) H 0.3118 0.2676 0.2472 0.0623 Uiso 1.00 calc . . . H(35) H 0.4346 0.3712 0.2344 0.0623 Uiso 1.00 calc . . . H(36) H 0.4134 0.3460 0.3936 0.0646 Uiso 1.00 calc . . . H(37) H 0.2588 0.3332 0.3891 0.0646 Uiso 1.00 calc . . . H(38) H 0.4662 0.5274 0.3712 0.0646 Uiso 1.00 calc . . . H(39) H 0.3579 0.5026 0.4521 0.0646 Uiso 1.00 calc . . . H(40) H 0.3234 0.6237 0.3350 0.0448 Uiso 1.00 calc . . . H(41) H 0.1969 0.5242 0.3520 0.0448 Uiso 1.00 calc . . . 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 Br(1) 0.0447(2) 0.0325(2) 0.0459(2) 0.0133(1) -0.0120(2) 0.0048(1) F(1) 0.044(1) 0.040(1) 0.059(1) 0.0234(9) -0.0081(9) 0.0092(9) F(2) 0.0181(8) 0.055(1) 0.057(1) 0.0110(8) 0.0075(8) 0.0050(9) F(3) 0.0192(8) 0.048(1) 0.043(1) 0.0115(7) 0.0072(7) 0.0015(8) F(4) 0.064(1) 0.0323(10) 0.062(1) 0.0318(9) -0.017(1) -0.0021(9) O(1) 0.0209(8) 0.0286(10) 0.0166(9) 0.0010(7) -0.0044(7) -0.0011(7) O(2) 0.0197(8) 0.0233(9) 0.0151(9) 0.0035(7) -0.0019(7) -0.0011(6) O(3) 0.0185(8) 0.0242(9) 0.0168(9) 0.0004(7) -0.0023(7) -0.0026(6) O(4) 0.0177(8) 0.0263(9) 0.0158(9) 0.0008(7) -0.0020(7) -0.0040(7) C(1) 0.017(1) 0.018(1) 0.022(1) -0.0005(9) -0.0017(9) -0.0002(9) C(2) 0.025(1) 0.026(1) 0.021(1) 0.006(1) -0.002(1) -0.0002(9) C(3) 0.031(1) 0.028(1) 0.029(2) 0.006(1) -0.006(1) 0.005(1) C(4) 0.025(1) 0.025(1) 0.042(2) 0.007(1) -0.004(1) 0.008(1) C(5) 0.029(1) 0.026(1) 0.038(2) 0.010(1) 0.007(1) 0.000(1) C(6) 0.028(1) 0.026(1) 0.022(1) 0.007(1) 0.004(1) -0.0009(10) C(7) 0.019(1) 0.028(1) 0.018(1) 0.0077(10) -0.0026(9) 0.0034(9) C(8) 0.021(1) 0.023(1) 0.024(1) 0.0063(9) 0.0000(10) 0.0028(9) C(9) 0.024(1) 0.037(2) 0.033(2) 0.015(1) 0.003(1) 0.004(1) C(10) 0.016(1) 0.043(2) 0.033(2) 0.010(1) 0.002(1) 0.007(1) C(11) 0.022(1) 0.038(2) 0.027(2) 0.002(1) -0.002(1) 0.004(1) C(12) 0.021(1) 0.027(1) 0.024(1) 0.0027(10) -0.002(1) -0.0013(10) C(13) 0.022(1) 0.021(1) 0.013(1) 0.0046(9) -0.0021(9) 0.0004(8) C(14) 0.018(1) 0.022(1) 0.016(1) 0.0068(9) -0.0026(9) -0.0010(8) C(15) 0.019(1) 0.020(1) 0.016(1) 0.0058(9) -0.0005(9) -0.0011(8) C(16) 0.022(1) 0.029(1) 0.024(1) 0.009(1) -0.0016(10) 0.0033(10) C(17) 0.021(1) 0.033(1) 0.029(2) 0.011(1) -0.002(1) 0.000(1) C(18) 0.017(1) 0.029(1) 0.030(2) 0.0077(10) 0.002(1) -0.002(1) C(19) 0.027(1) 0.036(2) 0.025(2) 0.012(1) 0.006(1) 0.004(1) C(20) 0.022(1) 0.032(1) 0.024(1) 0.011(1) -0.0009(10) 0.005(1) C(21) 0.022(1) 0.023(1) 0.020(1) 0.0099(10) 0.0005(10) 0.0019(9) C(22) 0.026(1) 0.023(1) 0.025(1) 0.0082(10) -0.005(1) -0.0001(9) C(23) 0.036(1) 0.024(1) 0.033(2) 0.010(1) -0.005(1) -0.001(1) C(24) 0.044(2) 0.026(1) 0.033(2) 0.022(1) -0.003(1) 0.000(1) C(25) 0.030(1) 0.036(2) 0.033(2) 0.018(1) -0.003(1) 0.002(1) C(26) 0.022(1) 0.029(1) 0.024(1) 0.010(1) -0.003(1) 0.0021(10) C(27) 0.016(1) 0.019(1) 0.018(1) 0.0037(9) -0.0044(9) -0.0014(8) C(28) 0.017(1) 0.018(1) 0.017(1) 0.0037(9) -0.0035(9) -0.0022(8) C(29) 0.015(1) 0.025(1) 0.017(1) 0.0019(9) -0.0012(9) -0.0029(9) C(30) 0.022(1) 0.037(2) 0.018(1) 0.006(1) -0.0016(10) 0.002(1) C(31) 0.021(1) 0.045(2) 0.024(1) 0.002(1) -0.006(1) -0.001(1) C(32) 0.031(2) 0.044(2) 0.037(2) -0.002(1) -0.002(1) -0.020(1) C(33) 0.038(2) 0.022(1) 0.050(2) 0.001(1) 0.001(1) -0.013(1) C(34) 0.029(1) 0.024(1) 0.039(2) 0.009(1) -0.002(1) -0.007(1) C(35) 0.053(2) 0.043(2) 0.045(2) 0.020(2) -0.003(2) 0.004(1) C(36) 0.089(3) 0.047(2) 0.039(2) 0.035(2) -0.015(2) -0.009(2) C(37) 0.081(3) 0.045(2) 0.046(2) 0.038(2) 0.002(2) 0.005(2) C(38) 0.055(2) 0.054(2) 0.055(2) 0.023(2) -0.004(2) 0.016(2) C(39) 0.068(3) 0.046(2) 0.046(2) 0.008(2) -0.021(2) 0.007(2) C(40) 0.050(2) 0.040(2) 0.028(2) 0.018(1) -0.001(1) -0.005(1) #------------------------------------------------------------------------------ _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br(1) C(35) 1.979(4) . . yes F(1) C(4) 1.362(3) . . yes F(2) C(10) 1.364(3) . . yes F(3) C(18) 1.362(3) . . yes F(4) C(24) 1.371(3) . . yes O(1) C(13) 1.433(3) . . yes O(2) C(27) 1.441(3) . . yes O(3) C(14) 1.426(3) . . yes O(3) C(29) 1.429(3) . . yes O(4) C(28) 1.425(3) . . yes O(4) C(29) 1.424(3) . . yes C(1) C(2) 1.394(4) . . yes C(1) C(6) 1.385(4) . . yes C(1) C(13) 1.532(3) . . yes C(2) C(3) 1.389(4) . . yes C(3) C(4) 1.381(4) . . yes C(4) C(5) 1.371(4) . . yes C(5) C(6) 1.398(4) . . yes C(7) C(8) 1.386(4) . . yes C(7) C(12) 1.400(4) . . yes C(7) C(13) 1.528(3) . . yes C(8) C(9) 1.399(4) . . yes C(9) C(10) 1.366(4) . . yes C(10) C(11) 1.378(4) . . yes C(11) C(12) 1.382(4) . . yes C(13) C(14) 1.563(3) . . yes C(14) C(28) 1.547(3) . . yes C(15) C(16) 1.393(3) . . yes C(15) C(20) 1.391(4) . . yes C(15) C(27) 1.532(3) . . yes C(16) C(17) 1.402(4) . . yes C(17) C(18) 1.360(4) . . yes C(18) C(19) 1.382(4) . . yes C(19) C(20) 1.390(4) . . yes C(21) C(22) 1.398(4) . . yes C(21) C(26) 1.393(3) . . yes C(21) C(27) 1.528(3) . . yes C(22) C(23) 1.394(4) . . yes C(23) C(24) 1.376(4) . . yes C(24) C(25) 1.369(4) . . yes C(25) C(26) 1.390(4) . . yes C(27) C(28) 1.540(3) . . yes C(29) C(30) 1.525(3) . . yes C(29) C(34) 1.519(4) . . yes C(30) C(31) 1.537(4) . . yes C(31) C(32) 1.524(5) . . yes C(32) C(33) 1.526(5) . . yes C(33) C(34) 1.533(4) . . yes C(35) C(36) 1.452(5) . . yes C(35) C(40) 1.511(5) . . yes C(36) C(37) 1.516(5) . . yes C(37) C(38) 1.489(6) . . yes C(38) C(39) 1.515(6) . . yes C(39) C(40) 1.510(5) . . yes #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(14) O(3) C(29) 108.7(2) . . . yes C(28) O(4) C(29) 109.8(2) . . . yes C(2) C(1) C(6) 118.7(2) . . . yes C(2) C(1) C(13) 120.5(2) . . . yes C(6) C(1) C(13) 120.7(2) . . . yes C(1) C(2) C(3) 120.9(2) . . . yes C(2) C(3) C(4) 118.4(3) . . . yes F(1) C(4) C(3) 118.7(3) . . . yes F(1) C(4) C(5) 118.6(3) . . . yes C(3) C(4) C(5) 122.6(3) . . . yes C(4) C(5) C(6) 118.0(3) . . . yes C(1) C(6) C(5) 121.2(3) . . . yes C(8) C(7) C(12) 118.5(2) . . . yes C(8) C(7) C(13) 124.7(2) . . . yes C(12) C(7) C(13) 116.7(2) . . . yes C(7) C(8) C(9) 120.8(2) . . . yes C(8) C(9) C(10) 118.4(3) . . . yes F(2) C(10) C(9) 118.8(3) . . . yes F(2) C(10) C(11) 118.3(3) . . . yes C(9) C(10) C(11) 122.9(2) . . . yes C(10) C(11) C(12) 118.0(3) . . . yes C(7) C(12) C(11) 121.3(3) . . . yes O(1) C(13) C(1) 110.8(2) . . . yes O(1) C(13) C(7) 104.1(2) . . . yes O(1) C(13) C(14) 107.0(2) . . . yes C(1) C(13) C(7) 111.6(2) . . . yes C(1) C(13) C(14) 110.7(2) . . . yes C(7) C(13) C(14) 112.4(2) . . . yes O(3) C(14) C(13) 108.2(2) . . . yes O(3) C(14) C(28) 102.0(2) . . . yes C(13) C(14) C(28) 116.3(2) . . . yes C(16) C(15) C(20) 118.5(2) . . . yes C(16) C(15) C(27) 123.4(2) . . . yes C(20) C(15) C(27) 118.0(2) . . . yes C(15) C(16) C(17) 120.8(2) . . . yes C(16) C(17) C(18) 118.2(2) . . . yes F(3) C(18) C(17) 118.9(2) . . . yes F(3) C(18) C(19) 117.8(3) . . . yes C(17) C(18) C(19) 123.4(2) . . . yes C(18) C(19) C(20) 117.6(3) . . . yes C(15) C(20) C(19) 121.5(2) . . . yes C(22) C(21) C(26) 119.1(2) . . . yes C(22) C(21) C(27) 119.6(2) . . . yes C(26) C(21) C(27) 121.3(2) . . . yes C(21) C(22) C(23) 120.7(2) . . . yes C(22) C(23) C(24) 117.8(3) . . . yes F(4) C(24) C(23) 117.7(3) . . . yes F(4) C(24) C(25) 119.0(3) . . . yes C(23) C(24) C(25) 123.4(3) . . . yes C(24) C(25) C(26) 118.4(2) . . . yes C(21) C(26) C(25) 120.6(3) . . . yes O(2) C(27) C(15) 107.5(2) . . . yes O(2) C(27) C(21) 111.3(2) . . . yes O(2) C(27) C(28) 103.2(2) . . . yes C(15) C(27) C(21) 111.5(2) . . . yes C(15) C(27) C(28) 112.2(2) . . . yes C(21) C(27) C(28) 110.8(2) . . . yes O(4) C(28) C(14) 103.4(2) . . . yes O(4) C(28) C(27) 106.6(2) . . . yes C(14) C(28) C(27) 119.0(2) . . . yes O(3) C(29) O(4) 106.4(2) . . . yes O(3) C(29) C(30) 109.4(2) . . . yes O(3) C(29) C(34) 110.6(2) . . . yes O(4) C(29) C(30) 108.7(2) . . . yes O(4) C(29) C(34) 109.4(2) . . . yes C(30) C(29) C(34) 112.3(2) . . . yes C(29) C(30) C(31) 108.7(2) . . . yes C(30) C(31) C(32) 111.4(2) . . . yes C(31) C(32) C(33) 111.3(2) . . . yes C(32) C(33) C(34) 111.2(3) . . . yes C(29) C(34) C(33) 111.1(2) . . . yes Br(1) C(35) C(36) 110.5(3) . . . yes Br(1) C(35) C(40) 109.8(2) . . . yes C(36) C(35) C(40) 115.2(3) . . . yes C(35) C(36) C(37) 112.3(3) . . . yes C(36) C(37) C(38) 113.5(3) . . . yes C(37) C(38) C(39) 111.6(3) . . . yes C(38) C(39) C(40) 114.1(3) . . . yes C(35) C(40) C(39) 111.4(3) . . . yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br(1) C(35) C(36) C(37) -175.7(3) . . . . yes Br(1) C(35) C(40) C(39) 174.6(3) . . . . yes F(1) C(4) C(3) C(2) 178.2(2) . . . . yes F(1) C(4) C(5) C(6) -178.4(2) . . . . yes F(2) C(10) C(9) C(8) -179.3(3) . . . . yes F(2) C(10) C(11) C(12) -179.8(3) . . . . yes F(3) C(18) C(17) C(16) 177.8(2) . . . . yes F(3) C(18) C(19) C(20) -178.5(3) . . . . yes F(4) C(24) C(23) C(22) -179.8(3) . . . . yes F(4) C(24) C(25) C(26) -179.2(3) . . . . yes O(1) C(13) C(1) C(2) -169.0(2) . . . . yes O(1) C(13) C(1) C(6) 14.7(3) . . . . yes O(1) C(13) C(7) C(8) -119.2(3) . . . . yes O(1) C(13) C(7) C(12) 57.8(3) . . . . yes O(1) C(13) C(14) O(3) 178.6(2) . . . . yes O(1) C(13) C(14) C(28) -67.5(2) . . . . yes O(2) C(27) C(15) C(16) -102.4(3) . . . . yes O(2) C(27) C(15) C(20) 74.0(3) . . . . yes O(2) C(27) C(21) C(22) -162.7(2) . . . . yes O(2) C(27) C(21) C(26) 19.6(3) . . . . yes O(2) C(27) C(28) O(4) 179.1(2) . . . . yes O(2) C(27) C(28) C(14) -64.6(2) . . . . yes O(3) C(14) C(13) C(1) -60.6(2) . . . . yes O(3) C(14) C(13) C(7) 64.8(2) . . . . yes O(3) C(14) C(28) O(4) -29.4(2) . . . . yes O(3) C(14) C(28) C(27) -147.3(2) . . . . yes O(3) C(29) O(4) C(28) -1.1(3) . . . . yes O(3) C(29) C(30) C(31) 179.4(2) . . . . yes O(3) C(29) C(34) C(33) 178.6(2) . . . . yes O(4) C(28) C(14) C(13) -146.9(2) . . . . yes O(4) C(28) C(27) C(15) 63.7(2) . . . . yes O(4) C(28) C(27) C(21) -61.7(2) . . . . yes O(4) C(29) O(3) C(14) -19.3(2) . . . . yes O(4) C(29) C(30) C(31) 63.7(3) . . . . yes O(4) C(29) C(34) C(33) -64.5(3) . . . . yes C(1) C(2) C(3) C(4) 0.0(4) . . . . yes C(1) C(6) C(5) C(4) 0.4(4) . . . . yes C(1) C(13) C(7) C(8) 121.2(3) . . . . yes C(1) C(13) C(7) C(12) -61.7(3) . . . . yes C(1) C(13) C(14) C(28) 53.3(3) . . . . yes C(2) C(1) C(6) C(5) -2.4(4) . . . . yes C(2) C(1) C(13) C(7) -53.5(3) . . . . yes C(2) C(1) C(13) C(14) 72.5(3) . . . . yes C(2) C(3) C(4) C(5) -2.2(4) . . . . yes C(3) C(2) C(1) C(6) 2.2(4) . . . . yes C(3) C(2) C(1) C(13) -174.1(2) . . . . yes C(3) C(4) C(5) C(6) 2.0(4) . . . . yes C(5) C(6) C(1) C(13) 173.9(2) . . . . yes C(6) C(1) C(13) C(7) 130.3(2) . . . . yes C(6) C(1) C(13) C(14) -103.8(3) . . . . yes C(7) C(8) C(9) C(10) -1.1(4) . . . . yes C(7) C(12) C(11) C(10) -0.7(4) . . . . yes C(7) C(13) C(14) C(28) 178.8(2) . . . . yes C(8) C(7) C(12) C(11) 1.9(4) . . . . yes C(8) C(7) C(13) C(14) -3.8(3) . . . . yes C(8) C(9) C(10) C(11) 2.3(5) . . . . yes C(9) C(8) C(7) C(12) -0.9(4) . . . . yes C(9) C(8) C(7) C(13) 176.1(2) . . . . yes C(9) C(10) C(11) C(12) -1.4(4) . . . . yes C(11) C(12) C(7) C(13) -175.4(2) . . . . yes C(12) C(7) C(13) C(14) 173.2(2) . . . . yes C(13) C(14) O(3) C(29) 153.1(2) . . . . yes C(13) C(14) C(28) C(27) 95.2(2) . . . . yes C(14) O(3) C(29) C(30) -136.5(2) . . . . yes C(14) O(3) C(29) C(34) 99.3(2) . . . . yes C(14) C(28) O(4) C(29) 19.0(2) . . . . yes C(14) C(28) C(27) C(15) 179.9(2) . . . . yes C(14) C(28) C(27) C(21) 54.5(3) . . . . yes C(15) C(16) C(17) C(18) 1.3(4) . . . . yes C(15) C(20) C(19) C(18) 0.1(4) . . . . yes C(15) C(27) C(21) C(22) -42.6(3) . . . . yes C(15) C(27) C(21) C(26) 139.7(2) . . . . yes C(16) C(15) C(20) C(19) -0.9(4) . . . . yes C(16) C(15) C(27) C(21) 135.3(2) . . . . yes C(16) C(15) C(27) C(28) 10.3(3) . . . . yes C(16) C(17) C(18) C(19) -2.3(4) . . . . yes C(17) C(16) C(15) C(20) 0.2(4) . . . . yes C(17) C(16) C(15) C(27) 176.7(2) . . . . yes C(17) C(18) C(19) C(20) 1.6(4) . . . . yes C(19) C(20) C(15) C(27) -177.6(3) . . . . yes C(20) C(15) C(27) C(21) -48.2(3) . . . . yes C(20) C(15) C(27) C(28) -173.2(2) . . . . yes C(21) C(22) C(23) C(24) -1.5(4) . . . . yes C(21) C(26) C(25) C(24) -0.4(5) . . . . yes C(22) C(21) C(26) C(25) -0.8(4) . . . . yes C(22) C(21) C(27) C(28) 83.2(3) . . . . yes C(22) C(23) C(24) C(25) 0.3(5) . . . . yes C(23) C(22) C(21) C(26) 1.8(4) . . . . yes C(23) C(22) C(21) C(27) -176.0(3) . . . . yes C(23) C(24) C(25) C(26) 0.6(5) . . . . yes C(25) C(26) C(21) C(27) 176.9(3) . . . . yes C(26) C(21) C(27) C(28) -94.5(3) . . . . yes C(27) C(28) O(4) C(29) 145.2(2) . . . . yes C(28) O(4) C(29) C(30) 116.5(2) . . . . yes C(28) O(4) C(29) C(34) -120.6(2) . . . . yes C(28) C(14) O(3) C(29) 30.0(2) . . . . yes C(29) C(30) C(31) C(32) 57.6(3) . . . . yes C(29) C(34) C(33) C(32) -53.6(3) . . . . yes C(30) C(29) C(34) C(33) 56.2(3) . . . . yes C(30) C(31) C(32) C(33) -57.0(3) . . . . yes C(31) C(30) C(29) C(34) -57.5(3) . . . . yes C(31) C(32) C(33) C(34) 54.3(3) . . . . yes C(35) C(36) C(37) C(38) 51.5(5) . . . . yes C(35) C(40) C(39) C(38) -48.1(5) . . . . yes C(36) C(35) C(40) C(39) 49.1(4) . . . . yes C(36) C(37) C(38) C(39) -50.7(5) . . . . yes C(37) C(36) C(35) C(40) -50.7(5) . . . . yes C(37) C(38) C(39) C(40) 49.9(5) . . . . yes C(37) C(38) C(39) C(40) 49.9(5) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F(1) C(38) 3.418(5) . 2_656 ? F(1) F(2) 3.475(3) . 1_655 ? F(2) C(4) 3.257(3) . 1_455 ? F(2) C(3) 3.446(3) . 1_455 ? F(2) C(30) 3.528(4) . 1_455 ? F(3) O(2) 3.051(3) . 2_755 ? F(3) C(6) 3.217(3) . 2_755 ? F(3) C(26) 3.219(3) . 1_655 ? F(3) C(25) 3.280(4) . 1_655 ? F(4) C(25) 3.249(3) . 2_665 ? F(4) F(4) 3.365(4) . 2_665 ? F(4) C(5) 3.466(4) . 1_565 ? O(1) O(2) 2.722(2) . 2_655 ? O(1) C(26) 3.576(3) . 2_655 ? O(2) O(2) 3.377(3) . 2_655 ? C(10) C(30) 3.595(4) . 2_656 ? #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_site_distance_DH _geom_hbond_site_distance_HA _geom_hbond_site_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1) O(2) . . . 0.829 1.826 2.624(2) 160.987 no O(2) H(11) O(1) . . 2_655 0.823 2.099 2.722(2) 132.374 no