# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Georghiou, Paris E.' 'Ashram, Muhammad' _publ_contact_author_name 'Dr Paris E Georghiou' _publ_contact_author_address ; Department of Chemistry Memorial Univesity of Newfoundland St John's Newfoundland CANADA ; _publ_contact_author_email 'PARISG@MUN.CA' _publ_section_title ; Chemical reactivity of hydroxymethylnaphthols: hetero-Diels-Alder products of 0-naphthoquinomethides derived from 2-and 3-hydroxymethylnaphthols ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1997-1998). teXsan for Windows version 1.03. Single Crystal Structure Analysis Software. Version 1.04. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Sheldrick, G.M. (1997). ; data__dmh-46 #(MAH 2002 paper; Compound 25a) _database_code_CSD 178406 _audit_creation_date '1999-10-06' _audit_creation_method 'by teXsan for Windows v1.0' _audit_update_record ; ? ; #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows (MSC, 1997)' _computing_structure_solution ; SHELX97 (Sheldrick, 1997) ; _computing_structure_refinement 'teXsan for Windows (MSC, 1997)' _computing_publication_material 'teXsan for Windows (MSC, 1997)' #------------------------------------------------------------------------------ _cell_length_a 6.237(1) _cell_length_b 26.725(2) _cell_length_c 16.872(2) _cell_angle_alpha 90 _cell_angle_beta 96.20(2) _cell_angle_gamma 90 _cell_volume 2795.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 20.1 _cell_measurement_theta_max 25.7 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 496.64 _chemical_formula_analytical ? _chemical_formula_sum 'C33 H36 O4 ' _chemical_formula_moiety 'C33 H36 O4 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1064.00 _exptl_absorpt_coefficient_mu 0.603 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.909 _exptl_special_details ; The scan width was (0.94+0.14tan\q)\% with an \w scan speed of 4\% per minute (up to 6 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.07 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -4 3 -1 -3 4 0 -4 4 _diffrn_reflns_number 4689 _reflns_number_total 4251 _reflns_number_gt 2008 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.03110 _diffrn_reflns_av_sigmaI/netI 0.148 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 60.07 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.01964 _diffrn_orient_matrix_UB_12 -0.02938 _diffrn_orient_matrix_UB_13 0.03677 _diffrn_orient_matrix_UB_21 -0.00457 _diffrn_orient_matrix_UB_22 0.02278 _diffrn_orient_matrix_UB_23 0.04682 _diffrn_orient_matrix_UB_31 -0.16001 _diffrn_orient_matrix_UB_32 -0.00426 _diffrn_orient_matrix_UB_33 -0.00331 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 132 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 144 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 16 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.0219(4) 0.2265(1) 0.4329(2) 0.063(1) 1.000 . Uani d ? O(2) 0.5817(5) 0.1361(1) 0.6707(2) 0.071(1) 1.000 . Uani d ? O(3) 0.9013(6) 0.1226(1) 0.7524(2) 0.116(2) 1.000 . Uani d ? O(4) -0.1086(5) 0.2519(1) 0.3047(2) 0.077(1) 1.000 . Uani d ? C(1) 0.1620(6) 0.1928(1) 0.4035(2) 0.048(1) 1.000 . Uani d ? C(2) 0.1457(6) 0.1837(2) 0.3206(2) 0.052(1) 1.000 . Uani d ? C(3) 0.2843(7) 0.1521(2) 0.2923(2) 0.057(1) 1.000 . Uani d ? C(4) 0.4437(6) 0.1262(1) 0.3427(2) 0.051(1) 1.000 . Uani d ? C(5) 0.5782(7) 0.0897(2) 0.3129(2) 0.064(1) 1.000 . Uani d ? C(6) 0.7212(7) 0.0615(2) 0.3605(3) 0.068(2) 1.000 . Uani d ? C(7) 0.7329(8) 0.0714(2) 0.4436(3) 0.080(2) 1.000 . Uani d ? C(8) 0.6106(7) 0.1070(2) 0.4742(2) 0.069(2) 1.000 . Uani d ? C(9) 0.4581(6) 0.1354(1) 0.4256(2) 0.050(1) 1.000 . Uani d ? C(10) 0.3147(6) 0.1706(1) 0.4566(2) 0.049(1) 1.000 . Uani d ? C(11) 0.3226(7) 0.1811(1) 0.5452(2) 0.055(1) 1.000 . Uani d ? C(12) 0.5264(6) 0.2054(1) 0.5847(2) 0.048(1) 1.000 . Uani d ? C(13) 0.6512(7) 0.1816(2) 0.6447(2) 0.055(1) 1.000 . Uani d ? C(14) 0.8492(7) 0.2007(2) 0.6808(2) 0.060(1) 1.000 . Uani d ? C(15) 0.9176(7) 0.2454(2) 0.6549(2) 0.061(1) 1.000 . Uani d ? C(16) 0.7933(6) 0.2737(1) 0.5966(2) 0.049(1) 1.000 . Uani d ? C(17) 0.8557(7) 0.3219(2) 0.5744(2) 0.059(1) 1.000 . Uani d ? C(18) 0.7330(7) 0.3516(2) 0.5220(2) 0.057(1) 1.000 . Uani d ? C(19) 0.5339(7) 0.3317(2) 0.4895(3) 0.061(1) 1.000 . Uani d ? C(20) 0.4644(6) 0.2853(1) 0.5081(2) 0.053(1) 1.000 . Uani d ? C(21) 0.5916(6) 0.2541(2) 0.5623(2) 0.050(1) 1.000 . Uani d ? C(22) -0.1600(7) 0.2392(2) 0.3800(3) 0.077(2) 1.000 . Uani d ? C(23) -0.0293(7) 0.2093(2) 0.2666(2) 0.068(2) 1.000 . Uani d ? C(24) 0.8506(8) 0.0187(2) 0.3301(3) 0.084(2) 1.000 . Uani d ? C(25) 0.848(1) 0.0185(3) 0.2420(4) 0.258(5) 1.000 . Uani d ? C(26) 1.0799(9) 0.0195(2) 0.3659(4) 0.115(2) 1.000 . Uani d ? C(27) 0.755(1) -0.0305(2) 0.3596(5) 0.167(3) 1.000 . Uani d ? C(28) 0.686(1) 0.1214(2) 0.7451(3) 0.102(2) 1.000 . Uani d ? C(29) 0.9812(8) 0.1716(2) 0.7448(3) 0.093(2) 1.000 . Uani d ? C(30) 0.8043(9) 0.4040(2) 0.4985(3) 0.076(2) 1.000 . Uani d ? C(31) 0.993(2) 0.4221(3) 0.5504(5) 0.225(4) 1.000 . Uani d ? C(32) 0.634(1) 0.4396(2) 0.4998(9) 0.356(7) 1.000 . Uani d ? C(33) 0.877(2) 0.4014(3) 0.4191(5) 0.218(5) 1.000 . Uani d ? H(1) 0.2761 0.1468 0.2364 0.069 1.000 . Uiso c ? H(2) 0.5686 0.0846 0.2570 0.076 1.000 . Uiso c ? H(3) 0.8301 0.0525 0.4789 0.096 1.000 . Uiso c ? H(4) 0.6284 0.1130 0.5301 0.083 1.000 . Uiso c ? H(5) 0.2054 0.2026 0.5529 0.066 1.000 . Uiso c ? H(6) 0.3051 0.1501 0.5713 0.066 1.000 . Uiso c ? H(7) 1.0537 0.2580 0.6768 0.073 1.000 . Uiso c ? H(8) 0.9909 0.3344 0.5974 0.070 1.000 . Uiso c ? H(9) 0.4436 0.3515 0.4530 0.073 1.000 . Uiso c ? H(10) 0.3286 0.2736 0.4843 0.064 1.000 . Uiso c ? H(11) -0.2555 0.2114 0.3752 0.093 1.000 . Uiso c ? H(12) -0.2298 0.2670 0.4014 0.093 1.000 . Uiso c ? H(13) -0.1444 0.1864 0.2536 0.081 1.000 . Uiso c ? H(14) 0.0276 0.2196 0.2192 0.081 1.000 . Uiso c ? H(15) 0.7205 0.0006 0.2196 0.308 1.000 . Uiso c ? H(16) 0.8423 0.0513 0.2225 0.308 1.000 . Uiso c ? H(17) 0.9707 0.0015 0.2276 0.308 1.000 . Uiso c ? H(18) 1.0850 0.0189 0.4224 0.137 1.000 . Uiso c ? H(19) 1.1530 -0.0090 0.3485 0.137 1.000 . Uiso c ? H(20) 1.1478 0.0491 0.3498 0.137 1.000 . Uiso c ? H(21) 0.7545 -0.0293 0.4156 0.201 1.000 . Uiso c ? H(22) 0.6114 -0.0344 0.3349 0.201 1.000 . Uiso c ? H(23) 0.8401 -0.0580 0.3455 0.201 1.000 . Uiso c ? H(24) 0.6383 0.1430 0.7844 0.123 1.000 . Uiso c ? H(25) 0.6427 0.0880 0.7548 0.123 1.000 . Uiso c ? H(26) 0.9785 0.1886 0.7941 0.112 1.000 . Uiso c ? H(27) 1.1255 0.1697 0.7319 0.112 1.000 . Uiso c ? H(28) 0.9609 0.4190 0.6047 0.275 1.000 . Uiso c ? H(29) 1.1134 0.4036 0.5421 0.275 1.000 . Uiso c ? H(30) 1.0123 0.4567 0.5395 0.275 1.000 . Uiso c ? H(31) 0.6048 0.4462 0.5521 0.421 1.000 . Uiso c ? H(32) 0.6720 0.4700 0.4746 0.421 1.000 . Uiso c ? H(33) 0.5056 0.4266 0.4696 0.421 1.000 . Uiso c ? H(34) 1.0256 0.3967 0.4233 0.265 1.000 . Uiso c ? H(35) 0.8029 0.3751 0.3903 0.265 1.000 . Uiso c ? H(36) 0.8395 0.4325 0.3922 0.265 1.000 . Uiso c ? 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 O(1) 0.053(2) 0.072(2) 0.062(2) 0.010(2) -0.000(2) -0.007(2) O(2) 0.092(2) 0.066(2) 0.051(2) -0.015(2) -0.016(2) 0.014(2) O(3) 0.118(3) 0.091(3) 0.125(3) -0.017(3) -0.048(3) 0.041(3) O(4) 0.089(2) 0.078(2) 0.065(2) 0.029(2) 0.010(2) 0.010(2) C(1) 0.046(2) 0.044(2) 0.053(3) -0.003(2) 0.002(2) -0.001(2) C(2) 0.055(3) 0.057(3) 0.043(3) 0.003(2) -0.005(2) 0.005(2) C(3) 0.070(3) 0.057(3) 0.042(2) -0.003(3) -0.005(2) 0.001(2) C(4) 0.056(3) 0.045(3) 0.052(3) -0.001(2) 0.003(2) -0.004(2) C(5) 0.075(3) 0.062(3) 0.052(3) 0.008(3) -0.002(2) -0.006(2) C(6) 0.082(3) 0.056(3) 0.062(3) 0.008(3) -0.006(3) -0.007(3) C(7) 0.092(4) 0.064(3) 0.075(4) 0.025(3) -0.025(3) -0.013(3) C(8) 0.088(4) 0.058(3) 0.056(3) 0.011(3) -0.016(3) -0.007(3) C(9) 0.064(3) 0.039(2) 0.045(2) -0.003(2) -0.007(2) -0.003(2) C(10) 0.051(3) 0.050(3) 0.043(2) -0.010(2) -0.003(2) -0.003(2) C(11) 0.066(3) 0.051(3) 0.046(2) -0.003(2) 0.001(2) -0.001(2) C(12) 0.062(3) 0.044(3) 0.039(2) -0.003(2) 0.001(2) -0.004(2) C(13) 0.070(3) 0.048(3) 0.045(2) -0.005(2) -0.001(2) -0.001(2) C(14) 0.067(3) 0.061(3) 0.049(3) 0.004(3) -0.007(2) -0.006(2) C(15) 0.061(3) 0.064(3) 0.055(3) -0.003(3) -0.010(2) -0.003(2) C(16) 0.048(3) 0.049(3) 0.051(3) -0.002(2) 0.004(2) -0.003(2) C(17) 0.060(3) 0.060(3) 0.055(3) -0.013(3) 0.004(2) -0.009(2) C(18) 0.063(3) 0.055(3) 0.055(3) -0.002(3) 0.013(2) -0.004(2) C(19) 0.066(3) 0.051(3) 0.066(3) 0.005(2) 0.004(3) 0.000(2) C(20) 0.055(3) 0.049(3) 0.056(3) 0.001(2) 0.000(2) -0.005(2) C(21) 0.057(3) 0.055(3) 0.039(2) 0.000(2) 0.006(2) -0.006(2) C(22) 0.060(3) 0.098(4) 0.073(3) 0.017(3) 0.006(3) -0.000(3) C(23) 0.071(3) 0.079(3) 0.052(3) 0.009(3) 0.004(2) 0.006(3) C(24) 0.070(3) 0.063(3) 0.118(5) 0.021(3) 0.003(3) -0.023(3) C(25) 0.35(1) 0.33(1) 0.086(5) 0.27(1) -0.036(6) -0.072(6) C(26) 0.084(4) 0.104(5) 0.156(6) 0.015(4) 0.015(4) -0.012(4) C(27) 0.127(6) 0.074(4) 0.30(1) -0.004(4) 0.050(6) -0.068(6) C(28) 0.116(5) 0.099(4) 0.084(4) -0.022(4) -0.025(4) 0.043(3) C(29) 0.104(4) 0.084(4) 0.082(4) -0.019(3) -0.032(3) 0.027(3) C(30) 0.104(4) 0.058(3) 0.065(3) -0.020(3) 0.004(3) 0.004(3) C(31) 0.33(1) 0.124(6) 0.188(7) -0.154(8) -0.111(8) 0.069(6) C(32) 0.156(7) 0.034(4) 0.92(3) 0.024(4) 0.23(1) 0.075(9) C(33) 0.37(1) 0.150(7) 0.145(7) -0.130(8) 0.077(8) 0.028(6) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00006|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000043(1) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2008 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1751 _refine_ls_R_factor_gt 0.0680 _refine_ls_wR_factor_all 0.0750 _refine_ls_wR_factor_ref 0.0660 _refine_ls_goodness_of_fit_all 1.651 _refine_ls_goodness_of_fit_ref 2.180 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.24 _refine_diff_density_max 0.00 #============================================================================== # MOLECULAR GEOMETRY _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 O1 C1 1.382(6) . . ? O1 C22 1.407(7) . . ? O2 C13 1.378(6) . . ? O2 C28 1.404(7) . . ? O3 C28 1.338(9) . . ? O3 C29 1.411(8) . . ? O4 C22 1.387(7) . . ? O4 C23 1.423(7) . . ? C1 C2 1.412(7) . . ? C1 C10 1.370(7) . . ? C2 C3 1.334(7) . . ? C2 C23 1.508(8) . . ? C3 C4 1.417(7) . . ? C3 H1 0.95 . . no C4 C5 1.413(7) . . ? C4 C9 1.414(7) . . ? C5 C6 1.362(8) . . ? C5 H2 0.95 . . no C6 C7 1.421(8) . . ? C6 C24 1.520(8) . . ? C7 C8 1.356(8) . . ? C7 H3 0.95 . . no C8 C9 1.409(8) . . ? C8 H4 0.95 . . no C9 C10 1.436(7) . . ? C10 C11 1.517(7) . . ? C11 C12 1.515(7) . . ? C11 H5 0.95 . . no C11 H6 0.95 . . no C12 C13 1.366(7) . . ? C12 C21 1.427(7) . . ? C13 C14 1.411(8) . . ? C14 C15 1.358(8) . . ? C14 C29 1.502(8) . . ? C15 C16 1.405(8) . . ? C15 H7 0.95 . . no C16 C17 1.409(8) . . ? C16 C21 1.426(7) . . ? C17 C18 1.360(8) . . ? C17 H8 0.95 . . no C18 C19 1.406(8) . . ? C18 C30 1.535(8) . . ? C19 C20 1.362(8) . . ? C19 H9 0.95 . . no C20 C21 1.416(8) . . ? C20 H10 0.95 . . no C22 H11 0.95 . . no C22 H12 0.95 . . no C23 H13 0.95 . . no C23 H14 0.95 . . no C24 C25 1.48(1) . . ? C24 C26 1.492(9) . . ? C24 C27 1.55(1) . . ? C25 H15 0.97 . . no C25 H16 0.94 . . no C25 H17 0.94 . . no C26 H18 0.95 . . no C26 H19 0.95 . . no C26 H20 0.95 . . no C27 H21 0.95 . . no C27 H22 0.95 . . no C27 H23 0.95 . . no C28 H24 0.95 . . no C28 H25 0.95 . . no C29 H26 0.95 . . no C29 H27 0.95 . . no C30 C31 1.47(1) . . ? C30 C32 1.43(1) . . ? C30 C33 1.46(1) . . ? C31 H28 0.96 . . no C31 H29 0.92 . . no C31 H30 0.95 . . no C32 H31 0.94 . . no C32 H32 0.96 . . no C32 H33 0.96 . . no C33 H34 0.93 . . no C33 H35 0.95 . . no C33 H36 0.96 . . no #------------------------------------------------------------------------------ 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 C1 O1 C22 115.3(5) . . . ? C13 O2 C28 113.6(5) . . . ? C28 O3 C29 112.0(7) . . . ? C22 O4 C23 110.1(5) . . . ? O1 C1 C2 119.1(5) . . . ? O1 C1 C10 118.0(5) . . . ? C2 C1 C10 122.9(6) . . . ? C1 C2 C3 118.9(5) . . . ? C1 C2 C23 119.4(6) . . . ? C3 C2 C23 121.7(6) . . . ? C2 C3 C4 122.3(6) . . . ? C2 C3 H1 118.9 . . . no C4 C3 H1 118.8 . . . no C3 C4 C5 121.9(6) . . . ? C3 C4 C9 118.3(6) . . . ? C5 C4 C9 119.6(6) . . . ? C4 C5 C6 123.3(6) . . . ? C4 C5 H2 118.4 . . . no C6 C5 H2 118.3 . . . no C5 C6 C7 116.0(6) . . . ? C5 C6 C24 123.7(6) . . . ? C7 C6 C24 120.1(6) . . . ? C6 C7 C8 122.4(6) . . . ? C6 C7 H3 118.7 . . . no C8 C7 H3 118.8 . . . no C7 C8 C9 121.9(6) . . . ? C7 C8 H4 119.1 . . . no C9 C8 H4 119.1 . . . no C4 C9 C8 116.7(6) . . . ? C4 C9 C10 119.9(5) . . . ? C8 C9 C10 123.3(5) . . . ? C1 C10 C9 117.6(5) . . . ? C1 C10 C11 120.6(6) . . . ? C9 C10 C11 121.7(5) . . . ? C10 C11 C12 116.7(5) . . . ? C10 C11 H5 107.7 . . . no C10 C11 H6 107.6 . . . no C12 C11 H5 107.7 . . . no C12 C11 H6 107.5 . . . no H5 C11 H6 109.5 . . . no C11 C12 C13 120.7(6) . . . ? C11 C12 C21 121.6(5) . . . ? C13 C12 C21 117.7(5) . . . ? O2 C13 C12 118.2(5) . . . ? O2 C13 C14 118.2(5) . . . ? C12 C13 C14 123.6(6) . . . ? C13 C14 C15 118.0(6) . . . ? C13 C14 C29 120.6(6) . . . ? C15 C14 C29 121.4(6) . . . ? C14 C15 C16 122.0(6) . . . ? C14 C15 H7 119.0 . . . no C16 C15 H7 119.0 . . . no C15 C16 C17 122.0(6) . . . ? C15 C16 C21 118.8(6) . . . ? C17 C16 C21 119.0(5) . . . ? C16 C17 C18 123.6(6) . . . ? C16 C17 H8 118.2 . . . no C18 C17 H8 118.2 . . . no C17 C18 C19 116.4(6) . . . ? C17 C18 C30 122.7(6) . . . ? C19 C18 C30 120.8(6) . . . ? C18 C19 C20 122.9(6) . . . ? C18 C19 H9 118.6 . . . no C20 C19 H9 118.4 . . . no C19 C20 C21 121.0(6) . . . ? C19 C20 H10 119.5 . . . no C21 C20 H10 119.5 . . . no C12 C21 C16 119.5(5) . . . ? C12 C21 C20 123.5(5) . . . ? C16 C21 C20 117.0(6) . . . ? O1 C22 O4 113.0(5) . . . ? O1 C22 H11 108.7 . . . no O1 C22 H12 108.7 . . . no O4 C22 H11 108.5 . . . no O4 C22 H12 108.5 . . . no H11 C22 H12 109.5 . . . no O4 C23 C2 110.7(5) . . . ? O4 C23 H13 109.2 . . . no O4 C23 H14 109.2 . . . no C2 C23 H13 109.1 . . . no C2 C23 H14 109.1 . . . no H13 C23 H14 109.5 . . . no C6 C24 C25 113.1(7) . . . ? C6 C24 C26 111.9(6) . . . ? C6 C24 C27 107.1(7) . . . ? C25 C24 C26 108.2(8) . . . ? C25 C24 C27 110.9(9) . . . ? C26 C24 C27 105.5(7) . . . ? C24 C25 H15 108.2 . . . no C24 C25 H16 110.2 . . . no C24 C25 H17 109.7 . . . no H15 C25 H16 109.1 . . . no H15 C25 H17 108.3 . . . no H16 C25 H17 111.2 . . . no C24 C26 H18 109.5 . . . no C24 C26 H19 109.5 . . . no C24 C26 H20 109.5 . . . no H18 C26 H19 109.5 . . . no H18 C26 H20 109.4 . . . no H19 C26 H20 109.5 . . . no C24 C27 H21 109.6 . . . no C24 C27 H22 109.2 . . . no C24 C27 H23 109.4 . . . no H21 C27 H22 109.5 . . . no H21 C27 H23 109.8 . . . no H22 C27 H23 109.3 . . . no O2 C28 O3 116.0(7) . . . ? O2 C28 H24 107.9 . . . no O2 C28 H25 107.8 . . . no O3 C28 H24 107.8 . . . no O3 C28 H25 107.7 . . . no H24 C28 H25 109.5 . . . no O3 C29 C14 112.0(6) . . . ? O3 C29 H26 108.9 . . . no O3 C29 H27 108.9 . . . no C14 C29 H26 108.8 . . . no C14 C29 H27 108.8 . . . no H26 C29 H27 109.5 . . . no C18 C30 C31 112.5(7) . . . ? C18 C30 C32 111.5(7) . . . ? C18 C30 C33 108.7(7) . . . ? C31 C30 C32 109(1) . . . ? C31 C30 C33 104.7(9) . . . ? C32 C30 C33 111(1) . . . ? C30 C31 H28 107.8 . . . no C30 C31 H29 110.3 . . . no C30 C31 H30 108.4 . . . no H28 C31 H29 110.7 . . . no H28 C31 H30 108.2 . . . no H29 C31 H30 111.5 . . . no C30 C32 H31 111.0 . . . no C30 C32 H32 109.6 . . . no C30 C32 H33 109.1 . . . no H31 C32 H32 110.1 . . . no H31 C32 H33 109.4 . . . no H32 C32 H33 107.6 . . . no C30 C33 H34 110.1 . . . no C30 C33 H35 108.8 . . . no C30 C33 H36 107.9 . . . no H34 C33 H35 111.4 . . . no H34 C33 H36 110.1 . . . no H35 C33 H36 108.5 . . . no #------------------------------------------------------------------------------ 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 O1 C16 3.480(7) . 1_455 no O2 C27 3.52(1) . 3_656 no O4 C29 3.345(9) . 4_354 no C20 C22 3.572(9) . 1_655 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C3 . . . . 178.5(6) no O1 C1 C2 C23 . . . . -2.4(8) no O1 C1 C10 C9 . . . . 179.4(5) no O1 C1 C10 C11 . . . . 2.5(8) no O1 C22 O4 C23 . . . . 67.0(7) no O2 C13 C12 C11 . . . . -2.8(9) no O2 C13 C12 C21 . . . . 175.4(5) no O2 C13 C14 C15 . . . . 179.8(6) no O2 C13 C14 C29 . . . . 0.9(9) no O2 C28 O3 C29 . . . . 64(1) no O3 C28 O2 C13 . . . . -51.3(9) no O3 C29 C14 C13 . . . . 10(1) no O3 C29 C14 C15 . . . . -169.2(7) no O4 C22 O1 C1 . . . . -48.3(8) no O4 C23 C2 C1 . . . . 19.7(8) no O4 C23 C2 C3 . . . . -161.3(6) no C1 C2 C3 C4 . . . . 1.8(9) no C1 C10 C9 C4 . . . . 2.4(8) no C1 C10 C9 C8 . . . . -174.8(6) no C1 C10 C11 C12 . . . . -118.3(6) no C2 C1 O1 C22 . . . . 15.6(8) no C2 C1 C10 C9 . . . . -2.2(8) no C2 C1 C10 C11 . . . . -179.1(5) no C2 C3 C4 C5 . . . . 174.7(6) no C2 C3 C4 C9 . . . . -1.5(9) no C2 C23 O4 C22 . . . . -50.1(7) no C3 C2 C1 C10 . . . . 0.1(9) no C3 C4 C5 C6 . . . . -174.8(6) no C3 C4 C9 C8 . . . . 176.7(6) no C3 C4 C9 C10 . . . . -0.6(8) no C4 C3 C2 C23 . . . . -177.2(6) no C4 C5 C6 C7 . . . . -1(1) no C4 C5 C6 C24 . . . . 173.8(6) no C4 C9 C8 C7 . . . . -2(1) no C4 C9 C10 C11 . . . . 179.2(5) no C5 C4 C9 C8 . . . . 0.4(8) no C5 C4 C9 C10 . . . . -176.9(5) no C5 C6 C7 C8 . . . . -0(1) no C5 C6 C24 C25 . . . . 14(1) no C5 C6 C24 C26 . . . . 136.8(8) no C5 C6 C24 C27 . . . . -108.1(9) no C6 C5 C4 C9 . . . . 1(1) no C6 C7 C8 C9 . . . . 2(1) no C7 C6 C24 C25 . . . . -171(1) no C7 C6 C24 C26 . . . . -48(1) no C7 C6 C24 C27 . . . . 66.9(9) no C7 C8 C9 C10 . . . . 175.1(7) no C8 C7 C6 C24 . . . . -175.7(7) no C8 C9 C10 C11 . . . . 2.1(9) no C9 C10 C11 C12 . . . . 65.0(8) no C10 C1 O1 C22 . . . . -166.0(5) no C10 C1 C2 C23 . . . . 179.2(6) no C10 C11 C12 C13 . . . . -118.9(6) no C10 C11 C12 C21 . . . . 63.0(8) no C11 C12 C13 C14 . . . . 176.1(6) no C11 C12 C21 C16 . . . . -175.0(5) no C11 C12 C21 C20 . . . . 6.1(9) no C12 C13 O2 C28 . . . . -163.6(6) no C12 C13 C14 C15 . . . . 0.9(9) no C12 C13 C14 C29 . . . . -178.0(6) no C12 C21 C16 C15 . . . . -3.4(8) no C12 C21 C16 C17 . . . . -179.8(6) no C12 C21 C20 C19 . . . . 179.4(6) no C13 C12 C21 C16 . . . . 6.8(8) no C13 C12 C21 C20 . . . . -172.1(6) no C13 C14 C15 C16 . . . . 3(1) no C14 C13 O2 C28 . . . . 17.5(8) no C14 C13 C12 C21 . . . . -5.7(9) no C14 C15 C16 C17 . . . . 174.7(6) no C14 C15 C16 C21 . . . . -1.5(9) no C14 C29 O3 C28 . . . . -39.6(9) no C15 C16 C17 C18 . . . . -175.7(6) no C15 C16 C21 C20 . . . . 175.6(6) no C16 C15 C14 C29 . . . . -178.3(6) no C16 C17 C18 C19 . . . . 0.1(9) no C16 C17 C18 C30 . . . . -179.9(6) no C16 C21 C20 C19 . . . . 0.4(9) no C17 C16 C21 C20 . . . . -0.7(8) no C17 C18 C19 C20 . . . . -0.5(9) no C17 C18 C30 C31 . . . . -12(1) no C17 C18 C30 C32 . . . . -134(1) no C17 C18 C30 C33 . . . . 103.5(9) no C18 C17 C16 C21 . . . . 0.5(9) no C18 C19 C20 C21 . . . . 0(1) no C19 C18 C30 C31 . . . . 168.1(9) no C19 C18 C30 C32 . . . . 46(1) no C19 C18 C30 C33 . . . . -76(1) no C20 C19 C18 C30 . . . . 179.5(6) no #------------------------------------------------------------------------------ #============================================================================== # 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 #============================================================================== data_schaulk _database_code_CSD 178407 _audit_creation_date '2001-09-25' _audit_creation_method 'by teXsan for Windows v1.06' _audit_update_record ; ? ; #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_structure_solution ; SHELX97 (Sheldrick, 1997) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-1999)' #------------------------------------------------------------------------------ _cell_length_a 8.911(4) _cell_length_b 12.901(2) _cell_length_c 8.346(8) _cell_angle_alpha 91.10(4) _cell_angle_beta 107.23(6) _cell_angle_gamma 106.15(2) _cell_volume 875(1) _cell_formula_units_Z 2 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 17.9 _cell_measurement_theta_max 21.7 #------------------------------------------------------------------------------ _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'parallelepiped' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 470.16 _chemical_formula_analytical ? _chemical_formula_sum 'C22 H14 Br2 O2 ' _chemical_formula_moiety 'C22 H14 Br2 O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 464.00 _exptl_absorpt_coefficient_mu 4.661 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.628 _exptl_special_details ; The scan width was (1.73+0.35tan\q)\% with an \w scan speed of 4\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.38 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 3 0 2 1 -1 1 4 -1 _diffrn_reflns_number 3314 _reflns_number_total 3094 _reflns_number_gt 1684 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.03860 _diffrn_reflns_av_sigmaI/netI 0.077 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.06006 _diffrn_orient_matrix_UB_12 0.07943 _diffrn_orient_matrix_UB_13 0.01888 _diffrn_orient_matrix_UB_21 -0.10519 _diffrn_orient_matrix_UB_22 0.01679 _diffrn_orient_matrix_UB_23 -0.00992 _diffrn_orient_matrix_UB_31 0.02171 _diffrn_orient_matrix_UB_32 -0.00160 _diffrn_orient_matrix_UB_33 0.12441 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 44 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 28 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 4 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Br 0 4 -0.374 2.456 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Br(1) 0.86791(7) 0.76298(5) 0.44448(8) 0.0462(2) 1.000 . Uani d ? Br(2) 0.12403(7) -0.09335(5) 0.19045(9) 0.0581(3) 1.000 . Uani d ? O(1) 0.6007(5) 0.2910(3) 0.0683(5) 0.065(2) 1.000 . Uani d ? O(3) 0.5199(4) 0.2817(3) 0.3626(4) 0.035(1) 1.000 . Uani d ? C(1) 0.4793(7) 0.2213(5) 0.0716(7) 0.037(2) 1.000 . Uani d ? C(2) 0.3984(6) 0.2321(4) 0.2051(7) 0.029(2) 1.000 . Uani d ? C(4) 0.5881(6) 0.3930(4) 0.3812(6) 0.025(2) 1.000 . Uani d ? C(5) 0.7344(6) 0.4332(4) 0.5200(7) 0.026(2) 1.000 . Uani d ? C(6) 0.7986(7) 0.3658(4) 0.6357(8) 0.037(2) 1.000 . Uani d ? C(7) 0.9398(7) 0.4054(5) 0.7673(7) 0.039(2) 1.000 . Uani d ? C(8) 1.0278(6) 0.5148(5) 0.7862(8) 0.044(2) 1.000 . Uani d ? C(9) 0.9725(7) 0.5838(4) 0.6789(8) 0.036(2) 1.000 . Uani d ? C(10) 0.8243(6) 0.5452(4) 0.5457(6) 0.026(2) 1.000 . Uani d ? C(11) 0.7552(6) 0.6125(4) 0.4300(7) 0.032(2) 1.000 . Uani d ? C(12) 0.6086(7) 0.5722(5) 0.3081(7) 0.036(2) 1.000 . Uani d ? C(13) 0.5216(6) 0.4603(4) 0.2797(6) 0.029(2) 1.000 . Uani d ? C(14) 0.3659(8) 0.4182(5) 0.1337(8) 0.038(2) 1.000 . Uani d ? C(15) 0.2779(6) 0.3002(5) 0.1432(7) 0.034(2) 1.000 . Uani d ? C(16) 0.3035(6) 0.1240(5) 0.2395(7) 0.034(2) 1.000 . Uani d ? C(17) 0.2539(6) 0.0369(4) 0.1321(7) 0.033(2) 1.000 . Uani d ? C(18) 0.2921(6) 0.0320(5) -0.0261(7) 0.035(2) 1.000 . Uani d ? C(19) 0.2289(7) -0.0594(5) -0.1437(9) 0.050(2) 1.000 . Uani d ? C(20) 0.2768(8) -0.0587(6) -0.2876(9) 0.060(3) 1.000 . Uani d ? C(21) 0.3862(9) 0.0312(7) -0.3146(8) 0.058(3) 1.000 . Uani d ? C(22) 0.4540(7) 0.1225(6) -0.1983(9) 0.048(2) 1.000 . Uani d ? C(23) 0.4054(6) 0.1252(5) -0.0534(7) 0.036(2) 1.000 . Uani d ? H(1) 0.747(5) 0.295(4) 0.618(6) 0.044 1.000 . Uiso d ? H(2) 0.985(5) 0.364(4) 0.843(6) 0.046 1.000 . Uiso d ? H(3) 1.122(5) 0.543(4) 0.868(6) 0.052 1.000 . Uiso d ? H(4) 1.028(5) 0.651(4) 0.683(6) 0.041 1.000 . Uiso d ? H(5) 0.573(6) 0.612(4) 0.247(6) 0.040 1.000 . Uiso d ? H(6) 0.291(5) 0.453(4) 0.140(6) 0.044 1.000 . Uiso d ? H(7) 0.386(5) 0.418(4) 0.029(6) 0.044 1.000 . Uiso d ? H(8) 0.204(5) 0.261(4) 0.031(5) 0.042 1.000 . Uiso d ? H(9) 0.211(5) 0.299(4) 0.221(5) 0.042 1.000 . Uiso d ? H(10) 0.269(5) 0.121(4) 0.341(5) 0.040 1.000 . Uiso d ? H(11) 0.150(6) -0.121(4) -0.115(6) 0.060 1.000 . Uiso d ? H(12) 0.222(6) -0.128(4) -0.377(6) 0.073 1.000 . Uiso d ? H(13) 0.421(6) 0.028(5) -0.396(6) 0.067 1.000 . Uiso d ? H(14) 0.544(5) 0.186(4) -0.206(6) 0.058 1.000 . Uiso d ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br(1) 0.0542(5) 0.0275(4) 0.0575(5) 0.0079(3) 0.0219(4) 0.0079(3) Br(2) 0.0529(5) 0.0367(5) 0.0733(6) 0.0001(4) 0.0152(4) 0.0100(4) O(1) 0.068(3) 0.050(3) 0.080(3) -0.006(2) 0.052(3) -0.010(3) O(3) 0.040(2) 0.027(2) 0.032(2) 0.009(2) 0.003(2) 0.005(2) C(1) 0.040(4) 0.037(4) 0.042(4) 0.019(3) 0.016(3) 0.015(3) C(2) 0.036(3) 0.017(3) 0.033(4) 0.005(3) 0.009(3) -0.001(3) C(4) 0.033(3) 0.020(3) 0.026(3) 0.005(3) 0.018(3) 0.003(3) C(5) 0.033(3) 0.026(3) 0.025(4) 0.013(3) 0.015(3) 0.006(3) C(6) 0.044(4) 0.026(4) 0.041(4) 0.012(3) 0.012(3) 0.006(3) C(7) 0.040(4) 0.042(4) 0.035(4) 0.021(3) 0.005(3) 0.015(3) C(8) 0.027(4) 0.051(5) 0.044(5) 0.006(3) 0.000(3) -0.001(4) C(9) 0.037(4) 0.031(4) 0.044(4) 0.010(3) 0.018(3) 0.003(3) C(10) 0.031(3) 0.026(3) 0.025(3) 0.011(3) 0.013(3) 0.005(3) C(11) 0.036(3) 0.028(3) 0.029(4) 0.000(3) 0.017(3) -0.006(3) C(12) 0.050(4) 0.034(4) 0.037(4) 0.019(3) 0.027(4) 0.016(3) C(13) 0.036(3) 0.035(4) 0.022(4) 0.014(3) 0.012(3) 0.004(3) C(14) 0.041(4) 0.043(4) 0.031(4) 0.013(3) 0.015(3) 0.006(3) C(15) 0.035(4) 0.046(4) 0.024(4) 0.017(3) 0.010(3) 0.001(3) C(16) 0.037(4) 0.031(4) 0.032(4) 0.012(3) 0.008(3) 0.006(3) C(17) 0.021(3) 0.027(3) 0.046(4) 0.002(3) 0.007(3) 0.007(3) C(18) 0.032(3) 0.041(4) 0.030(4) 0.019(3) -0.002(3) -0.003(3) C(19) 0.045(4) 0.050(5) 0.047(5) 0.015(3) 0.006(4) -0.005(4) C(20) 0.057(5) 0.061(6) 0.050(5) 0.026(4) -0.005(4) -0.026(4) C(21) 0.061(5) 0.097(6) 0.024(4) 0.047(5) 0.002(4) -0.006(5) C(22) 0.048(5) 0.060(5) 0.045(5) 0.032(4) 0.011(4) 0.011(4) C(23) 0.037(4) 0.040(4) 0.036(4) 0.024(3) 0.007(3) 0.003(3) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1684 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_all 0.0330 _refine_ls_wR_factor_ref 0.0270 _refine_ls_goodness_of_fit_all 1.346 _refine_ls_goodness_of_fit_ref 1.550 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.52 _refine_diff_density_max 0.51 #============================================================================== # MOLECULAR GEOMETRY _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(11) 1.905(6) . . ? Br(2) C(17) 1.919(6) . . ? O(1) C(1) 1.207(7) . . ? O(3) C(2) 1.431(7) . . ? O(3) C(4) 1.381(6) . . ? C(1) C(2) 1.519(8) . . ? C(1) C(23) 1.466(9) . . ? C(2) C(15) 1.551(8) . . ? C(2) C(16) 1.499(8) . . ? C(4) C(5) 1.420(8) . . ? C(4) C(13) 1.356(7) . . ? C(5) C(6) 1.413(8) . . ? C(5) C(10) 1.421(8) . . ? C(6) C(7) 1.361(9) . . ? C(6) H(1) 0.89(5) . . no C(7) C(8) 1.390(9) . . ? C(7) H(2) 0.91(5) . . no C(8) C(9) 1.360(9) . . ? C(8) H(3) 0.89(6) . . no C(9) C(10) 1.404(9) . . ? C(9) H(4) 0.86(5) . . no C(10) C(11) 1.429(8) . . ? C(11) C(12) 1.351(9) . . ? C(12) C(13) 1.412(9) . . ? C(12) H(5) 0.79(5) . . no C(13) C(14) 1.503(9) . . ? C(14) C(15) 1.52(1) . . ? C(14) H(6) 0.92(5) . . no C(14) H(7) 0.94(5) . . no C(15) H(8) 1.00(5) . . no C(15) H(9) 1.00(5) . . no C(16) C(17) 1.309(8) . . ? C(16) H(10) 0.98(5) . . no C(17) C(18) 1.462(8) . . ? C(18) C(19) 1.389(9) . . ? C(18) C(23) 1.410(8) . . ? C(19) C(20) 1.39(1) . . ? C(19) H(11) 0.99(6) . . no C(20) C(21) 1.36(1) . . ? C(20) H(12) 1.05(6) . . no C(21) C(22) 1.38(1) . . ? C(21) H(13) 0.83(6) . . no C(22) C(23) 1.403(9) . . ? C(22) H(14) 0.99(5) . . no #------------------------------------------------------------------------------ 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(2) O(3) C(4) 117.6(5) . . . ? O(1) C(1) C(2) 120.4(7) . . . ? O(1) C(1) C(23) 121.1(7) . . . ? C(2) C(1) C(23) 118.4(6) . . . ? O(3) C(2) C(1) 110.6(5) . . . ? O(3) C(2) C(15) 110.7(5) . . . ? O(3) C(2) C(16) 106.0(5) . . . ? C(1) C(2) C(15) 109.0(5) . . . ? C(1) C(2) C(16) 112.1(6) . . . ? C(15) C(2) C(16) 108.3(5) . . . ? O(3) C(4) C(5) 114.3(6) . . . ? O(3) C(4) C(13) 124.0(6) . . . ? C(5) C(4) C(13) 121.8(6) . . . ? C(4) C(5) C(6) 122.8(6) . . . ? C(4) C(5) C(10) 120.0(6) . . . ? C(6) C(5) C(10) 117.2(6) . . . ? C(5) C(6) C(7) 122.1(7) . . . ? C(5) C(6) H(1) 118(4) . . . no C(7) C(6) H(1) 120(4) . . . no C(6) C(7) C(8) 119.5(7) . . . ? C(6) C(7) H(2) 124(4) . . . no C(8) C(7) H(2) 116(4) . . . no C(7) C(8) C(9) 121.2(7) . . . ? C(7) C(8) H(3) 122(4) . . . no C(9) C(8) H(3) 117(4) . . . no C(8) C(9) C(10) 120.2(6) . . . ? C(8) C(9) H(4) 123(4) . . . no C(10) C(9) H(4) 117(4) . . . no C(5) C(10) C(9) 119.9(6) . . . ? C(5) C(10) C(11) 116.3(6) . . . ? C(9) C(10) C(11) 123.8(6) . . . ? Br(1) C(11) C(10) 120.5(5) . . . ? Br(1) C(11) C(12) 117.9(5) . . . ? C(10) C(11) C(12) 121.5(6) . . . ? C(11) C(12) C(13) 122.0(6) . . . ? C(11) C(12) H(5) 119(5) . . . no C(13) C(12) H(5) 119(5) . . . no C(4) C(13) C(12) 118.0(6) . . . ? C(4) C(13) C(14) 121.9(7) . . . ? C(12) C(13) C(14) 120.0(6) . . . ? C(13) C(14) C(15) 111.2(6) . . . ? C(13) C(14) H(6) 110(4) . . . no C(13) C(14) H(7) 112(4) . . . no C(15) C(14) H(6) 103(4) . . . no C(15) C(14) H(7) 105(4) . . . no H(6) C(14) H(7) 114(5) . . . no C(2) C(15) C(14) 112.7(6) . . . ? C(2) C(15) H(8) 104(3) . . . no C(2) C(15) H(9) 110(3) . . . no C(14) C(15) H(8) 113(3) . . . no C(14) C(15) H(9) 108(3) . . . no H(8) C(15) H(9) 109(4) . . . no C(2) C(16) C(17) 122.2(6) . . . ? C(2) C(16) H(10) 118(3) . . . no C(17) C(16) H(10) 119(3) . . . no Br(2) C(17) C(16) 116.8(5) . . . ? Br(2) C(17) C(18) 118.4(5) . . . ? C(16) C(17) C(18) 124.8(6) . . . ? C(17) C(18) C(19) 123.8(7) . . . ? C(17) C(18) C(23) 116.5(6) . . . ? C(19) C(18) C(23) 119.7(7) . . . ? C(18) C(19) C(20) 120.1(8) . . . ? C(18) C(19) H(11) 114(4) . . . no C(20) C(19) H(11) 126(4) . . . no C(19) C(20) C(21) 120.5(8) . . . ? C(19) C(20) H(12) 118(4) . . . no C(21) C(20) H(12) 121(4) . . . no C(20) C(21) C(22) 120.8(8) . . . ? C(20) C(21) H(13) 119(5) . . . no C(22) C(21) H(13) 119(5) . . . no C(21) C(22) C(23) 120.0(8) . . . ? C(21) C(22) H(14) 123(4) . . . no C(23) C(22) H(14) 117(4) . . . no C(1) C(23) C(18) 121.0(7) . . . ? C(1) C(23) C(22) 120.1(7) . . . ? C(18) C(23) C(22) 118.9(7) . . . ? #------------------------------------------------------------------------------ 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 O(1) C(8) 3.406(9) . 2_766 no C(1) C(20) 3.57(1) . 2_655 no C(5) C(9) 3.535(9) . 2_766 no C(8) C(10) 3.56(1) . 2_766 no C(17) C(21) 3.48(1) . 2_655 no C(18) C(22) 3.57(1) . 2_655 no C(19) C(23) 3.53(1) . 2_655 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br(1) C(11) C(10) C(5) . . . . -177.3(4) no Br(1) C(11) C(10) C(9) . . . . 2.5(9) no Br(1) C(11) C(12) C(13) . . . . 175.4(5) no Br(2) C(17) C(16) C(2) . . . . -176.9(5) no Br(2) C(17) C(18) C(19) . . . . 5.3(9) no Br(2) C(17) C(18) C(23) . . . . -171.8(4) no O(1) C(1) C(2) O(3) . . . . -36.5(8) no O(1) C(1) C(2) C(15) . . . . 85.5(8) no O(1) C(1) C(2) C(16) . . . . -154.6(6) no O(1) C(1) C(23) C(18) . . . . 163.6(6) no O(1) C(1) C(23) C(22) . . . . -13(1) no O(3) C(2) C(1) C(23) . . . . 144.2(5) no O(3) C(2) C(15) C(14) . . . . 54.2(8) no O(3) C(2) C(16) C(17) . . . . -141.0(6) no O(3) C(4) C(5) C(6) . . . . -4.0(9) no O(3) C(4) C(5) C(10) . . . . 175.0(5) no O(3) C(4) C(13) C(12) . . . . -177.0(6) no O(3) C(4) C(13) C(14) . . . . -1(1) no C(1) C(2) O(3) C(4) . . . . 78.7(6) no C(1) C(2) C(15) C(14) . . . . -67.7(7) no C(1) C(2) C(16) C(17) . . . . -20.2(9) no C(1) C(23) C(18) C(17) . . . . -0.2(9) no C(1) C(23) C(18) C(19) . . . . -177.5(6) no C(1) C(23) C(22) C(21) . . . . 179.0(7) no C(2) O(3) C(4) C(5) . . . . -164.8(5) no C(2) O(3) C(4) C(13) . . . . 16.6(8) no C(2) C(1) C(23) C(18) . . . . -17.1(9) no C(2) C(1) C(23) C(22) . . . . 166.6(6) no C(2) C(15) C(14) C(13) . . . . -39.0(8) no C(2) C(16) C(17) C(18) . . . . 4(1) no C(4) O(3) C(2) C(15) . . . . -42.2(7) no C(4) O(3) C(2) C(16) . . . . -159.5(5) no C(4) C(5) C(6) C(7) . . . . 179.4(7) no C(4) C(5) C(10) C(9) . . . . -177.3(6) no C(4) C(5) C(10) C(11) . . . . 2.5(8) no C(4) C(13) C(12) C(11) . . . . 1(1) no C(4) C(13) C(14) C(15) . . . . 13.4(9) no C(5) C(4) C(13) C(12) . . . . 4.5(9) no C(5) C(4) C(13) C(14) . . . . -179.4(6) no C(5) C(6) C(7) C(8) . . . . -2(1) no C(5) C(10) C(9) C(8) . . . . -2(1) no C(5) C(10) C(11) C(12) . . . . 3.0(9) no C(6) C(5) C(4) C(13) . . . . 174.6(6) no C(6) C(5) C(10) C(9) . . . . 1.7(9) no C(6) C(5) C(10) C(11) . . . . -178.5(6) no C(6) C(7) C(8) C(9) . . . . 2(1) no C(7) C(6) C(5) C(10) . . . . 0(1) no C(7) C(8) C(9) C(10) . . . . -0(1) no C(8) C(9) C(10) C(11) . . . . 178.3(6) no C(9) C(10) C(11) C(12) . . . . -177.2(6) no C(10) C(5) C(4) C(13) . . . . -6.4(9) no C(10) C(11) C(12) C(13) . . . . -5(1) no C(11) C(12) C(13) C(14) . . . . -175.0(6) no C(12) C(13) C(14) C(15) . . . . -170.6(6) no C(14) C(15) C(2) C(16) . . . . 170.1(6) no C(15) C(2) C(1) C(23) . . . . -93.9(7) no C(15) C(2) C(16) C(17) . . . . 100.1(7) no C(16) C(2) C(1) C(23) . . . . 26.0(8) no C(16) C(17) C(18) C(19) . . . . -175.4(7) no C(16) C(17) C(18) C(23) . . . . 7(1) no C(17) C(18) C(19) C(20) . . . . -177.3(7) no C(17) C(18) C(23) C(22) . . . . 176.2(6) no C(18) C(19) C(20) C(21) . . . . 0(1) no C(18) C(23) C(22) C(21) . . . . 3(1) no C(19) C(18) C(23) C(22) . . . . -1(1) no C(19) C(20) C(21) C(22) . . . . 1(1) no C(20) C(19) C(18) C(23) . . . . -0(1) no C(20) C(21) C(22) C(23) . . . . -3(1) no #------------------------------------------------------------------------------ #============================================================================== # 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 #============================================================================== data_3-mh-16 #(MAH 2002 Compound 27) _database_code_CSD 178408 _audit_creation_date '2001-09-25' _audit_creation_method 'by teXsan for Windows v1.06' _audit_update_record ; ? ; #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-1999)' #------------------------------------------------------------------------------ _cell_length_a 9.529(4) _cell_length_b 17.524(8) _cell_length_c 12.147(5) _cell_angle_alpha 90 _cell_angle_beta 98.82(4) _cell_angle_gamma 90 _cell_volume 2004(1) _cell_formula_units_Z 4 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.1 _cell_measurement_theta_max 18.2 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'irreg.' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 498.21 _chemical_formula_analytical ? _chemical_formula_sum 'C24 H18 Br2 O2 ' _chemical_formula_moiety 'C24 H18 Br2 O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 992.00 _exptl_absorpt_coefficient_mu 4.073 _exptl_absorpt_correction_type ? ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.566 _exptl_special_details ; The scan width was (0.94+0.35tan\q)\% with an \w scan speed of 8\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.11 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 2 2 2 1 1 2 -1 1 _diffrn_reflns_number 3913 _reflns_number_total 3683 _reflns_number_gt 1945 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.04400 _diffrn_reflns_av_sigmaI/netI 0.092 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.06 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.10367 _diffrn_orient_matrix_UB_12 -0.00351 _diffrn_orient_matrix_UB_13 0.02959 _diffrn_orient_matrix_UB_21 0.00456 _diffrn_orient_matrix_UB_22 -0.05051 _diffrn_orient_matrix_UB_23 -0.03760 _diffrn_orient_matrix_UB_31 0.02259 _diffrn_orient_matrix_UB_32 0.02632 _diffrn_orient_matrix_UB_33 -0.06820 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 96 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 72 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 8 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Br 0 8 -0.374 2.456 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Br(1) -0.63973(7) 0.02167(4) -0.78151(6) 0.0924(3) 1.000 . Uani d ? Br(2) -0.90103(6) -0.39895(3) -0.43139(5) 0.0600(2) 1.000 . Uani d ? O(1) -0.6252(3) -0.1158(2) -0.5418(3) 0.056(1) 1.000 . Uani d ? O(3) -0.7944(3) -0.2418(2) -0.5504(2) 0.039(1) 1.000 . Uani d ? C(1) -0.6275(4) -0.2793(2) -0.6728(4) 0.033(1) 1.000 . Uani d ? C(2) -0.6856(4) -0.2866(3) -0.5769(4) 0.034(2) 1.000 . Uani d ? C(4) -0.8418(4) -0.1784(3) -0.6209(4) 0.033(2) 1.000 . Uani d ? C(5) -0.9945(4) -0.1621(3) -0.6060(3) 0.033(2) 1.000 . Uani d ? C(6) -1.0849(5) -0.2208(3) -0.5859(4) 0.045(2) 1.000 . Uani d ? C(7) -1.2254(6) -0.2058(4) -0.5797(5) 0.055(2) 1.000 . Uani d ? C(8) -1.2781(5) -0.1324(4) -0.5973(4) 0.053(2) 1.000 . Uani d ? C(9) -1.1900(6) -0.0741(3) -0.6165(4) 0.048(2) 1.000 . Uani d ? C(10) -1.0453(5) -0.0876(3) -0.6211(4) 0.035(2) 1.000 . Uani d ? C(11) -0.9495(5) -0.0259(3) -0.6384(4) 0.043(2) 1.000 . Uani d ? C(12) -0.8080(5) -0.0345(3) -0.6270(4) 0.038(2) 1.000 . Uani d ? C(13) -0.7458(5) -0.1090(3) -0.5905(4) 0.036(2) 1.000 . Uani d ? C(14) -0.8366(5) -0.1989(3) -0.7446(4) 0.042(2) 1.000 . Uani d ? C(15) -0.6891(5) -0.2226(3) -0.7604(4) 0.044(2) 1.000 . Uani d ? C(16) -0.6401(4) -0.3434(3) -0.4960(4) 0.033(2) 1.000 . Uani d ? C(17) -0.5272(5) -0.3879(3) -0.5100(4) 0.037(2) 1.000 . Uani d ? C(18) -0.4549(4) -0.3793(2) -0.6018(4) 0.033(1) 1.000 . Uani d ? C(19) -0.3286(5) -0.4205(3) -0.6095(4) 0.044(2) 1.000 . Uani d ? C(20) -0.2562(5) -0.4094(3) -0.6963(5) 0.051(2) 1.000 . Uani d ? C(21) -0.3107(5) -0.3582(3) -0.7821(5) 0.048(2) 1.000 . Uani d ? C(22) -0.4319(5) -0.3175(3) -0.7776(4) 0.041(2) 1.000 . Uani d ? C(23) -0.5074(4) -0.3252(2) -0.6861(4) 0.031(1) 1.000 . Uani d ? C(24) -0.7127(6) 0.0304(3) -0.6400(5) 0.055(2) 1.000 . Uani d ? C(25) -0.7112(5) -0.3505(3) -0.3963(4) 0.046(2) 1.000 . Uani d ? H(1) -1.049(4) -0.273(2) -0.579(3) 0.054 1.000 . Uiso d ? H(2) -1.286(4) -0.246(2) -0.562(3) 0.060 1.000 . Uiso d ? H(3) -1.376(4) -0.123(2) -0.594(3) 0.062 1.000 . Uiso d ? H(4) -1.215(4) -0.024(2) -0.631(4) 0.055 1.000 . Uiso d ? H(5) -0.993(4) 0.022(2) -0.655(3) 0.049 1.000 . Uiso d ? H(6) -0.874(4) -0.151(2) -0.794(3) 0.046 1.000 . Uiso d ? H(7) -0.909(4) -0.245(2) -0.764(3) 0.046 1.000 . Uiso d ? H(8) -0.681(4) -0.237(2) -0.832(3) 0.049 1.000 . Uiso d ? H(9) -0.626(4) -0.177(2) -0.760(3) 0.049 1.000 . Uiso d ? H(10) -0.498(4) -0.427(2) -0.463(3) 0.039 1.000 . Uiso d ? H(11) -0.295(4) -0.458(2) -0.546(3) 0.052 1.000 . Uiso d ? H(12) -0.168(4) -0.436(2) -0.703(3) 0.054 1.000 . Uiso d ? H(13) -0.264(4) -0.350(3) -0.841(3) 0.060 1.000 . Uiso d ? H(14) -0.463(4) -0.285(2) -0.833(3) 0.047 1.000 . Uiso d ? H(15) -0.762(4) 0.080(2) -0.648(4) 0.063 1.000 . Uiso d ? H(16) -0.627(4) 0.027(3) -0.595(4) 0.063 1.000 . Uiso d ? H(17) -0.665(4) -0.386(2) -0.339(3) 0.051 1.000 . Uiso d ? H(18) -0.734(4) -0.303(2) -0.364(3) 0.051 1.000 . Uiso d ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br(1) 0.0967(5) 0.1023(6) 0.0915(6) -0.0188(5) 0.0569(4) -0.0004(5) Br(2) 0.0535(3) 0.0560(4) 0.0752(4) 0.0000(3) 0.0252(3) 0.0152(4) O(1) 0.039(2) 0.055(3) 0.069(3) -0.001(2) -0.000(2) 0.001(2) O(3) 0.046(2) 0.037(2) 0.036(2) 0.011(2) 0.011(2) 0.004(2) C(1) 0.037(3) 0.025(3) 0.037(3) 0.003(2) 0.005(2) 0.000(2) C(2) 0.038(3) 0.029(3) 0.036(3) 0.003(2) 0.006(2) 0.001(3) C(4) 0.034(3) 0.028(3) 0.037(3) 0.008(2) 0.006(2) 0.007(3) C(5) 0.034(3) 0.034(3) 0.030(3) -0.003(3) 0.002(2) -0.005(3) C(6) 0.038(3) 0.042(4) 0.051(4) -0.002(3) -0.006(3) -0.005(3) C(7) 0.041(4) 0.062(5) 0.059(4) -0.015(3) 0.003(3) -0.000(4) C(8) 0.032(3) 0.087(5) 0.042(4) -0.003(4) 0.009(3) -0.013(3) C(9) 0.046(3) 0.052(4) 0.046(4) 0.013(3) 0.009(3) 0.001(3) C(10) 0.035(3) 0.039(4) 0.031(3) 0.003(3) 0.004(2) -0.002(3) C(11) 0.055(4) 0.032(4) 0.043(3) 0.013(3) 0.013(3) 0.000(3) C(12) 0.043(3) 0.034(3) 0.040(3) -0.003(3) 0.012(2) 0.002(3) C(13) 0.035(3) 0.039(4) 0.038(3) 0.002(3) 0.013(2) -0.000(3) C(14) 0.045(3) 0.041(4) 0.037(3) 0.010(3) -0.000(3) 0.004(3) C(15) 0.050(3) 0.050(4) 0.034(3) 0.011(3) 0.015(3) 0.009(3) C(16) 0.039(3) 0.030(3) 0.033(3) -0.004(2) 0.011(2) 0.000(3) C(17) 0.045(3) 0.025(4) 0.038(3) 0.004(3) -0.000(3) 0.002(3) C(18) 0.037(3) 0.017(3) 0.046(3) -0.002(2) 0.007(2) -0.006(2) C(19) 0.047(3) 0.033(4) 0.052(4) 0.007(3) 0.007(3) -0.000(3) C(20) 0.042(3) 0.045(4) 0.067(4) 0.007(3) 0.009(3) -0.013(3) C(21) 0.049(3) 0.049(4) 0.053(4) -0.008(3) 0.025(3) -0.019(3) C(22) 0.046(3) 0.040(4) 0.038(3) -0.001(3) 0.010(3) 0.000(3) C(23) 0.037(3) 0.021(3) 0.035(3) -0.006(2) 0.004(2) -0.007(2) C(24) 0.054(4) 0.047(4) 0.069(4) 0.000(3) 0.022(3) 0.003(4) C(25) 0.047(3) 0.047(4) 0.043(4) 0.009(3) 0.004(3) 0.012(3) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.00000049(4) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1945 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1327 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_all 0.0370 _refine_ls_wR_factor_ref 0.0320 _refine_ls_goodness_of_fit_all 1.408 _refine_ls_goodness_of_fit_ref 1.670 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.77 _refine_diff_density_max 0.72 #============================================================================== # MOLECULAR GEOMETRY _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(24) 1.957(7) . . ? Br(2) C(25) 1.984(7) . . ? O(1) C(13) 1.215(6) . . ? O(3) C(2) 1.378(6) . . ? O(3) C(4) 1.433(6) . . ? C(1) C(2) 1.369(7) . . ? C(1) C(15) 1.508(8) . . ? C(1) C(23) 1.429(7) . . ? C(2) C(16) 1.420(7) . . ? C(4) C(5) 1.521(7) . . ? C(4) C(13) 1.533(7) . . ? C(4) C(14) 1.553(8) . . ? C(5) C(6) 1.386(8) . . ? C(5) C(10) 1.395(7) . . ? C(6) C(7) 1.379(8) . . ? C(6) H(1) 0.97(5) . . no C(7) C(8) 1.384(9) . . ? C(7) H(2) 0.95(5) . . no C(8) C(9) 1.366(9) . . ? C(8) H(3) 0.96(5) . . no C(9) C(10) 1.409(8) . . ? C(9) H(4) 0.91(5) . . no C(10) C(11) 1.451(8) . . ? C(11) C(12) 1.343(7) . . ? C(11) H(5) 0.94(5) . . no C(12) C(13) 1.473(8) . . ? C(12) C(24) 1.478(9) . . ? C(14) C(15) 1.506(8) . . ? C(14) H(6) 1.06(5) . . no C(14) H(7) 1.06(5) . . no C(15) H(8) 0.92(5) . . no C(15) H(9) 1.00(5) . . no C(16) C(17) 1.360(7) . . ? C(16) C(25) 1.480(8) . . ? C(17) C(18) 1.405(7) . . ? C(17) H(10) 0.91(5) . . no C(18) C(19) 1.418(7) . . ? C(18) C(23) 1.430(7) . . ? C(19) C(20) 1.360(8) . . ? C(19) H(11) 1.02(5) . . no C(20) C(21) 1.413(9) . . ? C(20) H(12) 0.97(5) . . no C(21) C(22) 1.366(8) . . ? C(21) H(13) 0.91(5) . . no C(22) C(23) 1.419(7) . . ? C(22) H(14) 0.90(5) . . no C(24) H(15) 0.99(5) . . no C(24) H(16) 0.91(5) . . no C(25) H(17) 0.99(5) . . no C(25) H(18) 0.96(5) . . no #------------------------------------------------------------------------------ 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(2) O(3) C(4) 118.8(4) . . . ? C(2) C(1) C(15) 119.9(5) . . . ? C(2) C(1) C(23) 118.7(5) . . . ? C(15) C(1) C(23) 121.5(5) . . . ? O(3) C(2) C(1) 124.2(5) . . . ? O(3) C(2) C(16) 113.5(5) . . . ? C(1) C(2) C(16) 122.3(5) . . . ? O(3) C(4) C(5) 107.1(4) . . . ? O(3) C(4) C(13) 110.5(5) . . . ? O(3) C(4) C(14) 110.1(5) . . . ? C(5) C(4) C(13) 111.7(5) . . . ? C(5) C(4) C(14) 109.3(5) . . . ? C(13) C(4) C(14) 108.1(5) . . . ? C(4) C(5) C(6) 120.9(6) . . . ? C(4) C(5) C(10) 118.6(5) . . . ? C(6) C(5) C(10) 120.4(5) . . . ? C(5) C(6) C(7) 120.2(6) . . . ? C(5) C(6) H(1) 119(3) . . . no C(7) C(6) H(1) 120(3) . . . no C(6) C(7) C(8) 120.1(7) . . . ? C(6) C(7) H(2) 120(4) . . . no C(8) C(7) H(2) 120(4) . . . no C(7) C(8) C(9) 120.2(6) . . . ? C(7) C(8) H(3) 120(4) . . . no C(9) C(8) H(3) 120(4) . . . no C(8) C(9) C(10) 120.8(6) . . . ? C(8) C(9) H(4) 127(4) . . . no C(10) C(9) H(4) 112(4) . . . no C(5) C(10) C(9) 118.3(6) . . . ? C(5) C(10) C(11) 120.2(5) . . . ? C(9) C(10) C(11) 121.4(6) . . . ? C(10) C(11) C(12) 123.0(6) . . . ? C(10) C(11) H(5) 115(3) . . . no C(12) C(11) H(5) 122(3) . . . no C(11) C(12) C(13) 118.8(6) . . . ? C(11) C(12) C(24) 121.7(6) . . . ? C(13) C(12) C(24) 119.2(6) . . . ? O(1) C(13) C(4) 121.6(6) . . . ? O(1) C(13) C(12) 122.7(6) . . . ? C(4) C(13) C(12) 115.6(5) . . . ? C(4) C(14) C(15) 110.9(5) . . . ? C(4) C(14) H(6) 108(3) . . . no C(4) C(14) H(7) 106(3) . . . no C(15) C(14) H(6) 113(3) . . . no C(15) C(14) H(7) 111(3) . . . no H(6) C(14) H(7) 109(4) . . . no C(1) C(15) C(14) 111.2(5) . . . ? C(1) C(15) H(8) 115(4) . . . no C(1) C(15) H(9) 111(3) . . . no C(14) C(15) H(8) 114(3) . . . no C(14) C(15) H(9) 110(3) . . . no H(8) C(15) H(9) 95(4) . . . no C(2) C(16) C(17) 118.5(5) . . . ? C(2) C(16) C(25) 119.7(5) . . . ? C(17) C(16) C(25) 121.7(6) . . . ? C(16) C(17) C(18) 122.2(6) . . . ? C(16) C(17) H(10) 122(3) . . . no C(18) C(17) H(10) 116(3) . . . no C(17) C(18) C(19) 121.5(6) . . . ? C(17) C(18) C(23) 118.6(5) . . . ? C(19) C(18) C(23) 119.8(6) . . . ? C(18) C(19) C(20) 121.1(6) . . . ? C(18) C(19) H(11) 116(3) . . . no C(20) C(19) H(11) 123(3) . . . no C(19) C(20) C(21) 119.3(6) . . . ? C(19) C(20) H(12) 123(3) . . . no C(21) C(20) H(12) 118(3) . . . no C(20) C(21) C(22) 121.3(6) . . . ? C(20) C(21) H(13) 120(4) . . . no C(22) C(21) H(13) 118(4) . . . no C(21) C(22) C(23) 121.0(6) . . . ? C(21) C(22) H(14) 119(4) . . . no C(23) C(22) H(14) 120(4) . . . no C(1) C(23) C(18) 119.4(5) . . . ? C(1) C(23) C(22) 123.1(6) . . . ? C(18) C(23) C(22) 117.4(5) . . . ? Br(1) C(24) C(12) 109.9(5) . . . ? Br(1) C(24) H(15) 102(3) . . . no Br(1) C(24) H(16) 97(4) . . . no C(12) C(24) H(15) 113(3) . . . no C(12) C(24) H(16) 113(4) . . . no H(15) C(24) H(16) 119(5) . . . no Br(2) C(25) C(16) 112.1(5) . . . ? Br(2) C(25) H(17) 100(3) . . . no Br(2) C(25) H(18) 102(3) . . . no C(16) C(25) H(17) 115(3) . . . no C(16) C(25) H(18) 115(3) . . . no H(17) C(25) H(18) 112(5) . . . no #------------------------------------------------------------------------------ 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 O(1) C(8) 3.487(7) . 1_655 no C(7) C(22) 3.469(9) . 1_455 no C(7) C(23) 3.493(9) . 1_455 no C(8) C(24) 3.40(1) . 3_354 no C(9) C(24) 3.47(1) . 3_354 no C(9) C(12) 3.520(9) . 3_354 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br(1) C(24) C(12) C(11) . . . . -106.4(6) no Br(1) C(24) C(12) C(13) . . . . 79.4(6) no Br(2) C(25) C(16) C(2) . . . . 75.1(7) no Br(2) C(25) C(16) C(17) . . . . -107.9(6) no O(1) C(13) C(4) O(3) . . . . 22.3(7) no O(1) C(13) C(4) C(5) . . . . 141.3(5) no O(1) C(13) C(4) C(14) . . . . -98.3(6) no O(1) C(13) C(12) C(11) . . . . -153.6(6) no O(1) C(13) C(12) C(24) . . . . 20.7(9) no O(3) C(2) C(1) C(15) . . . . -3.9(9) no O(3) C(2) C(1) C(23) . . . . 175.0(5) no O(3) C(2) C(16) C(17) . . . . -175.9(5) no O(3) C(2) C(16) C(25) . . . . 1.1(8) no O(3) C(4) C(5) C(6) . . . . -33.5(7) no O(3) C(4) C(5) C(10) . . . . 151.1(5) no O(3) C(4) C(13) C(12) . . . . -159.5(4) no O(3) C(4) C(14) C(15) . . . . -57.2(7) no C(1) C(2) O(3) C(4) . . . . -6.6(8) no C(1) C(2) C(16) C(17) . . . . 5.6(9) no C(1) C(2) C(16) C(25) . . . . -177.4(6) no C(1) C(15) C(14) C(4) . . . . 47.2(7) no C(1) C(23) C(18) C(17) . . . . 2.5(8) no C(1) C(23) C(18) C(19) . . . . -174.6(5) no C(1) C(23) C(22) C(21) . . . . 174.5(6) no C(2) O(3) C(4) C(5) . . . . 155.3(5) no C(2) O(3) C(4) C(13) . . . . -82.8(6) no C(2) O(3) C(4) C(14) . . . . 36.5(7) no C(2) C(1) C(15) C(14) . . . . -18.0(8) no C(2) C(1) C(23) C(18) . . . . 2.6(8) no C(2) C(1) C(23) C(22) . . . . -174.5(6) no C(2) C(16) C(17) C(18) . . . . -0.1(9) no C(4) O(3) C(2) C(16) . . . . 175.0(5) no C(4) C(5) C(6) C(7) . . . . -175.8(6) no C(4) C(5) C(10) C(9) . . . . 174.7(5) no C(4) C(5) C(10) C(11) . . . . -6.7(8) no C(4) C(13) C(12) C(11) . . . . 28.1(8) no C(4) C(13) C(12) C(24) . . . . -157.5(5) no C(5) C(4) C(13) C(12) . . . . -40.4(6) no C(5) C(4) C(14) C(15) . . . . -174.7(5) no C(5) C(6) C(7) C(8) . . . . 2(1) no C(5) C(10) C(9) C(8) . . . . 0(1) no C(5) C(10) C(11) C(12) . . . . -8.6(9) no C(6) C(5) C(4) C(13) . . . . -154.6(6) no C(6) C(5) C(4) C(14) . . . . 85.8(7) no C(6) C(5) C(10) C(9) . . . . -0.7(9) no C(6) C(5) C(10) C(11) . . . . 177.9(6) no C(6) C(7) C(8) C(9) . . . . -2(1) no C(7) C(6) C(5) C(10) . . . . -1(1) no C(7) C(8) C(9) C(10) . . . . 1(1) no C(8) C(9) C(10) C(11) . . . . -178.2(6) no C(9) C(10) C(11) C(12) . . . . 169.9(6) no C(10) C(5) C(4) C(13) . . . . 30.1(7) no C(10) C(5) C(4) C(14) . . . . -89.5(6) no C(10) C(11) C(12) C(13) . . . . -2.8(9) no C(10) C(11) C(12) C(24) . . . . -177.0(6) no C(12) C(13) C(4) C(14) . . . . 80.0(6) no C(13) C(4) C(14) C(15) . . . . 63.5(7) no C(14) C(15) C(1) C(23) . . . . 163.1(5) no C(15) C(1) C(2) C(16) . . . . 174.4(5) no C(15) C(1) C(23) C(18) . . . . -178.6(5) no C(15) C(1) C(23) C(22) . . . . 4.4(9) no C(16) C(2) C(1) C(23) . . . . -6.7(9) no C(16) C(17) C(18) C(19) . . . . 173.3(6) no C(16) C(17) C(18) C(23) . . . . -3.8(9) no C(17) C(18) C(19) C(20) . . . . -177.2(6) no C(17) C(18) C(23) C(22) . . . . 179.7(5) no C(18) C(17) C(16) C(25) . . . . -177.1(6) no C(18) C(19) C(20) C(21) . . . . -2(1) no C(18) C(23) C(22) C(21) . . . . -2.6(9) no C(19) C(18) C(23) C(22) . . . . 2.6(8) no C(19) C(20) C(21) C(22) . . . . 2(1) no C(20) C(19) C(18) C(23) . . . . -0.2(9) no C(20) C(21) C(22) C(23) . . . . 0(1) no #------------------------------------------------------------------------------ #============================================================================== # 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 #============================================================================== data_dmh-51-3 _database_code_CSD 178409 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_structure_solution ; SHELX97 (Sheldrick, 1997) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-1999)' #------------------------------------------------------------------------------ _cell_length_a 7.271(1) _cell_length_b 31.618(1) _cell_length_c 16.619(1) _cell_angle_alpha 90 _cell_angle_beta 92.647(2) _cell_angle_gamma 90 _cell_volume 3816.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 23.8 _cell_measurement_theta_max 29.6 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 510.18 _chemical_formula_analytical ? _chemical_formula_sum 'C24 H14 Br2 O3 ' _chemical_formula_moiety '?' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 2016.00 _exptl_absorpt_coefficient_mu 5.597 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.564 _exptl_special_details ; The scan width was (1.05+0.14tan\q)\% with an \w scan speed of 4\% per minute (up to 6 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -1.01 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 1 -4 -1 -1 -4 -1 4 -4 _diffrn_reflns_number 6329 _reflns_number_total 5815 _reflns_number_gt 3282 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.03710 _diffrn_reflns_av_sigmaI/netI 0.132 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 60.07 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00298 _diffrn_orient_matrix_UB_12 -0.00215 _diffrn_orient_matrix_UB_13 -0.05996 _diffrn_orient_matrix_UB_21 0.00444 _diffrn_orient_matrix_UB_22 -0.03154 _diffrn_orient_matrix_UB_23 0.00422 _diffrn_orient_matrix_UB_31 -0.13757 _diffrn_orient_matrix_UB_32 -0.00106 _diffrn_orient_matrix_UB_33 -0.00395 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 192 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 112 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 24 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Br 0 16 -0.767 1.283 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Br(1) 0.4275(1) 0.37916(2) 0.46705(5) 0.0605(3) 1.000 . Uani d ? Br(2) 0.2630(1) 0.15945(2) 0.28633(5) 0.0626(3) 1.000 . Uani d ? Br(3) 0.9947(1) 0.44214(3) 0.50911(5) 0.0709(3) 1.000 . Uani d ? Br(4) 0.8081(1) 0.22810(3) 0.30801(6) 0.0624(3) 1.000 . Uani d ? O(1) 0.4148(6) 0.2143(1) 0.4980(3) 0.046(1) 1.000 . Uani d ? O(2) 0.1027(7) 0.1464(2) 0.5431(3) 0.064(2) 1.000 . Uani d ? O(3) 0.8339(6) 0.3931(1) 0.2929(3) 0.047(1) 1.000 . Uani d ? O(4) 1.1631(8) 0.4505(2) 0.2529(3) 0.070(2) 1.000 . Uani d ? O(5) 1.317(1) 0.5100(2) 0.1650(4) 0.092(3) 1.000 . Uani d ? O(6) -0.0041(9) 0.0845(2) 0.6381(3) 0.082(2) 1.000 . Uani d ? C(1) 0.3936(9) 0.2504(2) 0.4517(4) 0.038(2) 1.000 . Uani d ? C(2) 0.425(1) 0.2909(2) 0.4845(4) 0.040(2) 1.000 . Uani d ? C(3) 0.3949(9) 0.3228(2) 0.4294(4) 0.040(2) 1.000 . Uani d ? C(4) 0.3320(9) 0.3168(2) 0.3464(4) 0.038(2) 1.000 . Uani d ? C(5) 0.295(1) 0.3507(2) 0.2926(5) 0.047(2) 1.000 . Uani d ? C(6) 0.235(1) 0.3435(2) 0.2149(5) 0.057(3) 1.000 . Uani d ? C(7) 0.210(1) 0.3020(2) 0.1871(4) 0.052(2) 1.000 . Uani d ? C(8) 0.246(1) 0.2688(2) 0.2371(4) 0.045(2) 1.000 . Uani d ? C(9) 0.3061(9) 0.2744(2) 0.3180(4) 0.038(2) 1.000 . Uani d ? C(10) 0.3363(9) 0.2407(2) 0.3741(4) 0.039(2) 1.000 . Uani d ? C(11) 0.3236(9) 0.1954(2) 0.3734(4) 0.039(2) 1.000 . Uani d ? C(12) 0.371(1) 0.1809(2) 0.4471(4) 0.047(2) 1.000 . Uani d ? C(13) 0.391(1) 0.1380(2) 0.4836(4) 0.048(2) 1.000 . Uani d ? C(14) 0.255(1) 0.1234(2) 0.5321(4) 0.050(2) 1.000 . Uani d ? C(15) 0.276(1) 0.0828(2) 0.5695(4) 0.053(3) 1.000 . Uani d ? C(16) 0.428(1) 0.0596(2) 0.5568(4) 0.058(3) 1.000 . Uani d ? C(17) 0.566(1) 0.0730(2) 0.5075(4) 0.049(2) 1.000 . Uani d ? C(18) 0.722(1) 0.0484(3) 0.4904(5) 0.070(3) 1.000 . Uani d ? C(19) 0.853(1) 0.0615(3) 0.4424(6) 0.073(3) 1.000 . Uani d ? C(20) 0.832(1) 0.1031(4) 0.4092(6) 0.085(4) 1.000 . Uani d ? C(21) 0.685(1) 0.1278(3) 0.4206(5) 0.062(3) 1.000 . Uani d ? C(22) 0.548(1) 0.1135(2) 0.4703(4) 0.047(2) 1.000 . Uani d ? C(23) 0.492(1) 0.2962(2) 0.5706(5) 0.056(2) 1.000 . Uani d ? C(24) 0.140(1) 0.0667(3) 0.6241(5) 0.064(3) 1.000 . Uani d ? C(26) 0.8478(9) 0.3561(2) 0.3367(4) 0.041(2) 1.000 . Uani d ? C(27) 0.8148(9) 0.3167(2) 0.3018(4) 0.037(2) 1.000 . Uani d ? C(28) 0.8428(9) 0.2831(2) 0.3530(4) 0.040(2) 1.000 . Uani d ? C(29) 0.9032(9) 0.2870(2) 0.4348(4) 0.043(2) 1.000 . Uani d ? C(30) 0.936(1) 0.2519(2) 0.4860(5) 0.057(3) 1.000 . Uani d ? C(31) 0.992(1) 0.2573(3) 0.5632(5) 0.064(3) 1.000 . Uani d ? C(32) 1.018(1) 0.2974(3) 0.5973(4) 0.059(3) 1.000 . Uani d ? C(33) 0.988(1) 0.3319(3) 0.5510(4) 0.052(2) 1.000 . Uani d ? C(34) 0.9317(9) 0.3282(2) 0.4681(4) 0.042(2) 1.000 . Uani d ? C(35) 0.9039(9) 0.3635(2) 0.4153(4) 0.040(2) 1.000 . Uani d ? C(36) 0.9233(9) 0.4085(2) 0.4203(4) 0.045(2) 1.000 . Uani d ? C(37) 0.884(1) 0.4253(2) 0.3467(4) 0.044(2) 1.000 . Uani d ? C(38) 0.891(1) 0.4683(2) 0.3132(4) 0.049(2) 1.000 . Uani d ? C(39) 1.035(1) 0.4796(2) 0.2683(4) 0.051(2) 1.000 . Uani d ? C(40) 1.046(1) 0.5219(2) 0.2354(5) 0.057(3) 1.000 . Uani d ? C(41) 0.917(1) 0.5497(3) 0.2519(5) 0.064(3) 1.000 . Uani d ? C(42) 0.762(1) 0.5407(2) 0.2983(5) 0.056(3) 1.000 . Uani d ? C(43) 0.625(1) 0.5699(3) 0.3149(6) 0.076(3) 1.000 . Uani d ? C(44) 0.476(1) 0.5582(3) 0.3570(6) 0.077(3) 1.000 . Uani d ? C(45) 0.463(1) 0.5174(3) 0.3857(5) 0.082(4) 1.000 . Uani d ? C(46) 0.595(1) 0.4877(3) 0.3737(5) 0.068(3) 1.000 . Uani d ? C(47) 0.752(1) 0.4978(2) 0.3286(4) 0.053(2) 1.000 . Uani d ? C(48) 0.747(1) 0.3143(2) 0.2147(4) 0.054(2) 1.000 . Uani d ? C(49) 1.197(1) 0.5335(3) 0.1852(5) 0.070(3) 1.000 . Uani d ? H(5) 0.4379 0.0355 0.5856 0.069 1.000 . Uiso c ? H(6) 0.7391 0.0242 0.5201 0.084 1.000 . Uiso c ? H(7) 0.9602 0.0532 0.4252 0.086 1.000 . Uiso c ? H(8) 0.9299 0.1118 0.3851 0.102 1.000 . Uiso c ? H(9) 0.6877 0.1517 0.4012 0.074 1.000 . Uiso c ? H(13) 0.1645 0.0373 0.6373 0.079 1.000 . Uiso c ? H(14) 0.0312 0.1268 0.5720 0.075 1.000 . Uiso c ? H(19) 0.9320 0.5774 0.2374 0.077 1.000 . Uiso c ? H(20) 0.6284 0.5966 0.2947 0.089 1.000 . Uiso c ? H(21) 0.3835 0.5782 0.3661 0.092 1.000 . Uiso c ? H(22) 0.3574 0.5105 0.4149 0.100 1.000 . Uiso c ? H(23) 0.5939 0.4649 0.3959 0.080 1.000 . Uiso c ? H(27) 1.1844 0.5631 0.1774 0.084 1.000 . Uiso c ? H(28) 1.2527 0.4646 0.2177 0.082 1.000 . Uiso c ? H(1) 0.3132 0.3788 0.3109 0.058 1.000 . Uiso c ? H(2) 0.2076 0.3667 0.1802 0.068 1.000 . Uiso c ? H(3) 0.1701 0.2970 0.1326 0.063 1.000 . Uiso c ? H(4) 0.2303 0.2410 0.2169 0.056 1.000 . Uiso c ? H(10) 0.3977 0.2885 0.6050 0.068 1.000 . Uiso c ? H(11) 0.5955 0.2775 0.5807 0.068 1.000 . Uiso c ? H(12) 0.5297 0.3242 0.5799 0.068 1.000 . Uiso c ? H(15) 0.9186 0.2240 0.4658 0.067 1.000 . Uiso c ? H(16) 1.0154 0.2332 0.5954 0.079 1.000 . Uiso c ? H(17) 1.0543 0.3003 0.6524 0.072 1.000 . Uiso c ? H(18) 1.0063 0.3596 0.5741 0.060 1.000 . Uiso c ? H(24) 0.6170 0.3100 0.2126 0.065 1.000 . Uiso c ? H(25) 0.7746 0.3399 0.1885 0.065 1.000 . Uiso c ? H(26) 0.8047 0.2913 0.1896 0.065 1.000 . Uiso c ? 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) 0.0649(6) 0.0379(4) 0.0786(6) -0.0037(4) 0.0032(5) -0.0104(4) Br(2) 0.0937(7) 0.0415(4) 0.0516(5) -0.0013(5) -0.0062(5) -0.0081(4) Br(3) 0.0891(7) 0.0592(6) 0.0629(6) 0.0059(5) -0.0117(5) -0.0200(5) Br(4) 0.0693(6) 0.0423(5) 0.0759(6) -0.0056(5) 0.0084(5) -0.0043(5) O(1) 0.060(3) 0.037(3) 0.039(3) -0.001(2) -0.009(2) -0.002(2) O(2) 0.066(4) 0.062(4) 0.062(4) 0.002(3) 0.001(3) -0.005(3) O(3) 0.059(3) 0.042(3) 0.039(3) -0.003(3) -0.002(2) 0.004(2) O(4) 0.073(4) 0.054(3) 0.083(4) 0.002(3) 0.020(3) 0.009(3) O(5) 0.112(6) 0.069(5) 0.098(5) -0.018(4) 0.028(4) 0.008(4) O(6) 0.084(5) 0.085(5) 0.078(4) -0.008(4) 0.022(4) 0.003(4) C(1) 0.030(4) 0.037(4) 0.048(4) 0.006(3) -0.002(3) 0.004(4) C(2) 0.046(4) 0.038(4) 0.035(4) -0.005(4) 0.004(3) -0.004(3) C(3) 0.035(4) 0.034(4) 0.051(5) 0.001(3) 0.005(3) -0.007(3) C(4) 0.033(4) 0.036(4) 0.045(4) 0.003(3) 0.007(3) 0.004(3) C(5) 0.047(5) 0.037(4) 0.059(5) 0.003(4) 0.011(4) -0.001(4) C(6) 0.055(5) 0.055(5) 0.060(5) -0.000(4) 0.012(4) 0.023(4) C(7) 0.055(5) 0.058(5) 0.045(5) 0.002(4) 0.003(4) 0.006(4) C(8) 0.053(5) 0.044(4) 0.038(4) 0.000(4) 0.005(4) -0.004(4) C(9) 0.031(4) 0.035(4) 0.048(4) 0.000(3) -0.000(3) 0.002(4) C(10) 0.038(4) 0.042(4) 0.036(4) -0.002(3) -0.003(3) 0.001(3) C(11) 0.046(5) 0.032(4) 0.040(4) -0.003(3) 0.008(3) -0.005(3) C(12) 0.062(5) 0.040(4) 0.039(4) 0.001(4) -0.006(4) 0.002(4) C(13) 0.073(6) 0.035(4) 0.034(4) 0.004(4) -0.012(4) -0.003(3) C(14) 0.060(5) 0.050(5) 0.039(4) 0.004(4) -0.001(4) -0.003(4) C(15) 0.075(6) 0.045(5) 0.039(4) -0.002(5) 0.001(4) -0.002(4) C(16) 0.087(7) 0.040(4) 0.046(5) -0.001(5) -0.005(5) 0.005(4) C(17) 0.058(5) 0.038(4) 0.048(5) 0.003(4) -0.019(4) -0.007(4) C(18) 0.086(7) 0.058(6) 0.065(6) 0.009(6) -0.009(5) -0.016(5) C(19) 0.070(7) 0.077(7) 0.070(6) 0.024(6) -0.005(5) -0.016(5) C(20) 0.075(7) 0.103(8) 0.076(7) -0.007(6) 0.007(6) -0.007(6) C(21) 0.063(6) 0.059(5) 0.064(6) 0.004(5) -0.001(5) -0.010(5) C(22) 0.058(5) 0.047(5) 0.035(4) -0.003(4) -0.008(4) -0.009(4) C(23) 0.059(5) 0.042(4) 0.065(5) -0.009(4) -0.003(4) -0.002(4) C(24) 0.070(6) 0.054(5) 0.070(6) -0.007(5) 0.008(5) -0.003(5) C(26) 0.040(4) 0.039(4) 0.044(4) 0.004(3) 0.011(3) 0.012(3) C(27) 0.033(4) 0.040(4) 0.038(4) -0.004(3) 0.002(3) -0.007(3) C(28) 0.038(4) 0.040(4) 0.043(4) -0.006(3) 0.005(3) -0.007(3) C(29) 0.033(4) 0.047(4) 0.052(5) 0.008(4) 0.019(4) 0.003(4) C(30) 0.050(5) 0.051(5) 0.071(6) 0.010(4) 0.009(4) 0.018(5) C(31) 0.048(5) 0.076(6) 0.068(6) 0.020(5) 0.013(5) 0.035(5) C(32) 0.054(5) 0.095(7) 0.029(4) 0.018(5) 0.010(4) 0.021(5) C(33) 0.041(5) 0.069(5) 0.046(5) -0.003(4) 0.007(4) 0.002(4) C(34) 0.027(4) 0.059(5) 0.040(4) 0.005(4) 0.005(3) 0.005(4) C(35) 0.047(5) 0.036(4) 0.037(4) 0.012(4) 0.003(3) 0.006(3) C(36) 0.038(4) 0.052(5) 0.045(4) 0.006(4) 0.000(3) -0.007(4) C(37) 0.046(5) 0.037(4) 0.047(5) -0.005(4) -0.001(4) 0.007(4) C(38) 0.051(5) 0.044(4) 0.052(5) 0.003(4) -0.012(4) 0.004(4) C(39) 0.059(5) 0.037(4) 0.058(5) -0.011(4) -0.003(4) 0.009(4) C(40) 0.070(6) 0.043(5) 0.059(5) -0.009(5) 0.002(4) 0.003(4) C(41) 0.088(7) 0.044(5) 0.059(5) -0.006(5) -0.014(5) -0.002(4) C(42) 0.081(7) 0.041(4) 0.044(5) 0.007(5) -0.021(5) -0.013(4) C(43) 0.098(8) 0.046(5) 0.083(7) 0.011(6) -0.017(6) -0.005(5) C(44) 0.079(7) 0.066(6) 0.085(7) 0.026(6) -0.013(6) -0.011(6) C(45) 0.072(7) 0.103(8) 0.070(6) 0.011(6) 0.000(5) -0.013(6) C(46) 0.065(6) 0.059(5) 0.078(6) 0.019(5) -0.006(5) 0.001(5) C(47) 0.059(5) 0.052(5) 0.046(5) -0.004(4) -0.015(4) -0.001(4) C(48) 0.054(5) 0.058(5) 0.048(5) -0.002(4) -0.003(4) -0.003(4) C(49) 0.101(8) 0.041(5) 0.067(6) -0.011(5) -0.007(6) -0.007(5) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00008|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3282 _refine_ls_number_parameters 523 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1262 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_all 0.0550 _refine_ls_wR_factor_ref 0.0450 _refine_ls_goodness_of_fit_all 1.222 _refine_ls_goodness_of_fit_ref 1.360 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.52 _refine_diff_density_max 0.43 #============================================================================== # MOLECULAR GEOMETRY _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(3) 1.900(7) . . ? Br(2) C(11) 1.877(7) . . ? Br(3) C(36) 1.873(8) . . ? Br(4) C(28) 1.905(7) . . ? O(1) C(1) 1.382(9) . . ? O(1) C(12) 1.382(9) . . ? O(2) C(14) 1.35(1) . . ? O(2) H(14) 0.95 . . no O(3) C(26) 1.379(9) . . ? O(3) C(37) 1.391(9) . . ? O(4) C(39) 1.34(1) . . ? O(4) H(28) 1.00 . . no O(5) C(49) 1.21(1) . . ? O(6) C(24) 1.22(1) . . ? C(1) C(2) 1.41(1) . . ? C(1) C(10) 1.37(1) . . ? C(2) C(3) 1.37(1) . . ? C(2) C(23) 1.50(1) . . ? C(3) C(4) 1.44(1) . . ? C(4) C(5) 1.41(1) . . ? C(4) C(9) 1.43(1) . . ? C(5) C(6) 1.36(1) . . ? C(5) H(1) 0.95 . . no C(6) C(7) 1.40(1) . . ? C(6) H(2) 0.95 . . no C(7) C(8) 1.36(1) . . ? C(7) H(3) 0.95 . . no C(8) C(9) 1.41(1) . . ? C(8) H(4) 0.94 . . no C(9) C(10) 1.43(1) . . ? C(10) C(11) 1.44(1) . . ? C(11) C(12) 1.34(1) . . ? C(12) C(13) 1.49(1) . . ? C(13) C(14) 1.39(1) . . ? C(13) C(22) 1.41(1) . . ? C(14) C(15) 1.43(1) . . ? C(15) C(16) 1.35(1) . . ? C(15) C(24) 1.46(1) . . ? C(16) C(17) 1.39(1) . . ? C(16) H(5) 0.90 . . no C(17) C(18) 1.41(1) . . ? C(17) C(22) 1.42(1) . . ? C(18) C(19) 1.34(1) . . ? C(18) H(6) 0.92 . . no C(19) C(20) 1.43(1) . . ? C(19) H(7) 0.88 . . no C(20) C(21) 1.34(1) . . ? C(20) H(8) 0.88 . . no C(21) C(22) 1.40(1) . . ? C(21) H(9) 0.82 . . no C(23) H(10) 0.94 . . no C(23) H(11) 0.97 . . no C(23) H(12) 0.94 . . no C(24) H(13) 0.97 . . no C(26) C(27) 1.39(1) . . ? C(26) C(35) 1.37(1) . . ? C(27) C(28) 1.37(1) . . ? C(27) C(48) 1.51(1) . . ? C(28) C(29) 1.41(1) . . ? C(29) C(30) 1.41(1) . . ? C(29) C(34) 1.43(1) . . ? C(30) C(31) 1.34(1) . . ? C(30) H(15) 0.95 . . no C(31) C(32) 1.40(1) . . ? C(31) H(16) 0.94 . . no C(32) C(33) 1.35(1) . . ? C(32) H(17) 0.95 . . no C(33) C(34) 1.42(1) . . ? C(33) H(18) 0.96 . . no C(34) C(35) 1.43(1) . . ? C(35) C(36) 1.43(1) . . ? C(36) C(37) 1.35(1) . . ? C(37) C(38) 1.47(1) . . ? C(38) C(39) 1.36(1) . . ? C(38) C(47) 1.41(1) . . ? C(39) C(40) 1.45(1) . . ? C(40) C(41) 1.33(1) . . ? C(40) C(49) 1.46(1) . . ? C(41) C(42) 1.42(1) . . ? C(41) H(19) 0.92 . . no C(42) C(43) 1.39(1) . . ? C(42) C(47) 1.45(1) . . ? C(43) C(44) 1.37(1) . . ? C(43) H(20) 0.91 . . no C(44) C(45) 1.38(1) . . ? C(44) H(21) 0.94 . . no C(45) C(46) 1.37(1) . . ? C(45) H(22) 0.95 . . no C(46) C(47) 1.43(1) . . ? C(46) H(23) 0.81 . . no C(48) H(24) 0.95 . . no C(48) H(25) 0.95 . . no C(48) H(26) 0.95 . . no C(49) H(27) 0.95 . . no #------------------------------------------------------------------------------ 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(1) O(1) C(12) 105.8(6) . . . ? C(14) O(2) H(14) 100.8 . . . no C(26) O(3) C(37) 105.6(6) . . . ? C(39) O(4) H(28) 106.6 . . . no O(1) C(1) C(2) 121.6(7) . . . ? O(1) C(1) C(10) 111.1(7) . . . ? C(2) C(1) C(10) 127.2(7) . . . ? C(1) C(2) C(3) 113.1(7) . . . ? C(1) C(2) C(23) 120.7(7) . . . ? C(3) C(2) C(23) 126.2(7) . . . ? Br(1) C(3) C(2) 117.0(6) . . . ? Br(1) C(3) C(4) 117.9(6) . . . ? C(2) C(3) C(4) 125.0(7) . . . ? C(3) C(4) C(5) 123.1(7) . . . ? C(3) C(4) C(9) 118.0(7) . . . ? C(5) C(4) C(9) 118.9(7) . . . ? C(4) C(5) C(6) 121.0(8) . . . ? C(4) C(5) H(1) 119.3 . . . no C(6) C(5) H(1) 119.7 . . . no C(5) C(6) C(7) 119.9(8) . . . ? C(5) C(6) H(2) 119.7 . . . no C(7) C(6) H(2) 120.4 . . . no C(6) C(7) C(8) 120.5(8) . . . ? C(6) C(7) H(3) 119.8 . . . no C(8) C(7) H(3) 119.7 . . . no C(7) C(8) C(9) 121.9(8) . . . ? C(7) C(8) H(4) 119.1 . . . no C(9) C(8) H(4) 119.0 . . . no C(4) C(9) C(8) 117.7(7) . . . ? C(4) C(9) C(10) 118.0(7) . . . ? C(8) C(9) C(10) 124.2(7) . . . ? C(1) C(10) C(9) 118.6(7) . . . ? C(1) C(10) C(11) 104.3(7) . . . ? C(9) C(10) C(11) 137.1(7) . . . ? Br(2) C(11) C(10) 128.6(6) . . . ? Br(2) C(11) C(12) 122.6(6) . . . ? C(10) C(11) C(12) 108.7(7) . . . ? O(1) C(12) C(11) 110.0(7) . . . ? O(1) C(12) C(13) 115.4(6) . . . ? C(11) C(12) C(13) 134.6(7) . . . ? C(12) C(13) C(14) 118.7(8) . . . ? C(12) C(13) C(22) 120.3(8) . . . ? C(14) C(13) C(22) 120.9(8) . . . ? O(2) C(14) C(13) 120.8(8) . . . ? O(2) C(14) C(15) 120.0(8) . . . ? C(13) C(14) C(15) 119.2(9) . . . ? C(14) C(15) C(16) 119.4(9) . . . ? C(14) C(15) C(24) 121.2(9) . . . ? C(16) C(15) C(24) 119.3(9) . . . ? C(15) C(16) C(17) 123.0(8) . . . ? C(15) C(16) H(5) 115.0 . . . no C(17) C(16) H(5) 121.8 . . . no C(16) C(17) C(18) 123.9(9) . . . ? C(16) C(17) C(22) 118.3(9) . . . ? C(18) C(17) C(22) 117.7(9) . . . ? C(17) C(18) C(19) 123(1) . . . ? C(17) C(18) H(6) 116.2 . . . no C(19) C(18) H(6) 119.9 . . . no C(18) C(19) C(20) 117(1) . . . ? C(18) C(19) H(7) 139.9 . . . no C(20) C(19) H(7) 103.2 . . . no C(19) C(20) C(21) 123(1) . . . ? C(19) C(20) H(8) 112.9 . . . no C(21) C(20) H(8) 123.3 . . . no C(20) C(21) C(22) 119(1) . . . ? C(20) C(21) H(9) 116.4 . . . no C(22) C(21) H(9) 124.1 . . . no C(13) C(22) C(17) 119.1(8) . . . ? C(13) C(22) C(21) 121.2(8) . . . ? C(17) C(22) C(21) 119.6(9) . . . ? C(2) C(23) H(10) 109.8 . . . no C(2) C(23) H(11) 108.2 . . . no C(2) C(23) H(12) 109.9 . . . no H(10) C(23) H(11) 108.7 . . . no H(10) C(23) H(12) 111.2 . . . no H(11) C(23) H(12) 109.0 . . . no O(6) C(24) C(15) 125(1) . . . ? O(6) C(24) H(13) 123.2 . . . no C(15) C(24) H(13) 110.5 . . . no O(3) C(26) C(27) 122.2(7) . . . ? O(3) C(26) C(35) 111.7(7) . . . ? C(27) C(26) C(35) 126.1(7) . . . ? C(26) C(27) C(28) 114.7(7) . . . ? C(26) C(27) C(48) 119.3(7) . . . ? C(28) C(27) C(48) 126.0(7) . . . ? Br(4) C(28) C(27) 116.8(6) . . . ? Br(4) C(28) C(29) 119.1(6) . . . ? C(27) C(28) C(29) 124.0(7) . . . ? C(28) C(29) C(30) 123.1(8) . . . ? C(28) C(29) C(34) 119.1(8) . . . ? C(30) C(29) C(34) 117.8(8) . . . ? C(29) C(30) C(31) 120.9(9) . . . ? C(29) C(30) H(15) 120.0 . . . no C(31) C(30) H(15) 119.0 . . . no C(30) C(31) C(32) 122.1(9) . . . ? C(30) C(31) H(16) 118.7 . . . no C(32) C(31) H(16) 119.2 . . . no C(31) C(32) C(33) 119.2(8) . . . ? C(31) C(32) H(17) 120.4 . . . no C(33) C(32) H(17) 120.4 . . . no C(32) C(33) C(34) 121.2(9) . . . ? C(32) C(33) H(18) 119.6 . . . no C(34) C(33) H(18) 119.2 . . . no C(29) C(34) C(33) 118.7(8) . . . ? C(29) C(34) C(35) 117.4(7) . . . ? C(33) C(34) C(35) 123.8(8) . . . ? C(26) C(35) C(34) 118.7(7) . . . ? C(26) C(35) C(36) 104.4(7) . . . ? C(34) C(35) C(36) 136.9(8) . . . ? Br(3) C(36) C(35) 129.2(6) . . . ? Br(3) C(36) C(37) 122.1(7) . . . ? C(35) C(36) C(37) 108.7(7) . . . ? O(3) C(37) C(36) 109.5(7) . . . ? O(3) C(37) C(38) 116.4(7) . . . ? C(36) C(37) C(38) 134.0(8) . . . ? C(37) C(38) C(39) 119.6(8) . . . ? C(37) C(38) C(47) 120.4(8) . . . ? C(39) C(38) C(47) 120.1(8) . . . ? O(4) C(39) C(38) 118.8(8) . . . ? O(4) C(39) C(40) 120.6(9) . . . ? C(38) C(39) C(40) 120.5(9) . . . ? C(39) C(40) C(41) 118.8(9) . . . ? C(39) C(40) C(49) 120.5(9) . . . ? C(41) C(40) C(49) 120.7(9) . . . ? C(40) C(41) C(42) 124.4(9) . . . ? C(40) C(41) H(19) 118.9 . . . no C(42) C(41) H(19) 116.4 . . . no C(41) C(42) C(43) 124(1) . . . ? C(41) C(42) C(47) 115.4(9) . . . ? C(43) C(42) C(47) 120(1) . . . ? C(42) C(43) C(44) 121(1) . . . ? C(42) C(43) H(20) 120.6 . . . no C(44) C(43) H(20) 118.4 . . . no C(43) C(44) C(45) 120(1) . . . ? C(43) C(44) H(21) 119.4 . . . no C(45) C(44) H(21) 120.8 . . . no C(44) C(45) C(46) 122(1) . . . ? C(44) C(45) H(22) 117.4 . . . no C(46) C(45) H(22) 120.3 . . . no C(45) C(46) C(47) 120(1) . . . ? C(45) C(46) H(23) 121.5 . . . no C(47) C(46) H(23) 117.7 . . . no C(38) C(47) C(42) 120.7(9) . . . ? C(38) C(47) C(46) 122.9(9) . . . ? C(42) C(47) C(46) 116.4(9) . . . ? C(27) C(48) H(24) 108.8 . . . no C(27) C(48) H(25) 109.3 . . . no C(27) C(48) H(26) 109.2 . . . no H(24) C(48) H(25) 109.7 . . . no H(24) C(48) H(26) 109.6 . . . no H(25) C(48) H(26) 110.1 . . . no O(5) C(49) C(40) 125.3(9) . . . ? O(5) C(49) H(27) 129.5 . . . no C(40) C(49) H(27) 104.9 . . . no #------------------------------------------------------------------------------ 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 Br(1) C(44) 3.57(1) . 3_666 no O(1) C(31) 3.57(1) . 1_455 no O(2) C(20) 3.21(1) . 1_455 no O(2) C(48) 3.24(1) . 4_455 no O(3) C(24) 3.33(1) . 4_554 no O(3) O(6) 3.546(9) . 4_554 no O(4) O(6) 3.340(9) . 4_654 no O(4) C(5) 3.36(1) . 1_655 no O(4) C(6) 3.49(1) . 1_655 no O(5) O(6) 3.30(1) . 4_654 no O(5) C(19) 3.46(1) . 2_755 no O(5) C(24) 3.47(1) . 4_654 no O(5) C(18) 3.48(1) . 4_554 no O(6) C(6) 3.26(1) . 4_455 no O(6) C(18) 3.29(1) . 1_455 no O(6) C(19) 3.45(1) . 1_455 no C(1) C(30) 3.40(1) . 1_455 no C(1) C(31) 3.54(1) . 1_455 no C(2) C(32) 3.58(1) . 1_455 no C(3) C(34) 3.46(1) . 1_455 no C(5) C(26) 3.37(1) . 1_455 no C(6) C(27) 3.54(1) . 1_455 no C(6) C(26) 3.56(1) . 1_455 no C(7) C(48) 3.45(1) . 1_455 no C(7) C(31) 3.51(1) . 4_454 no C(7) C(27) 3.55(1) . 1_455 no C(8) C(31) 3.57(1) . 4_454 no C(9) C(28) 3.46(1) . 1_455 no C(10) C(30) 3.54(1) . 1_455 no C(19) C(24) 3.60(1) . 1_655 no C(20) C(41) 3.58(1) . 2_645 no C(23) C(32) 3.49(1) . 1_455 no C(44) C(49) 3.51(1) . 1_455 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br(1) C(3) C(2) C(1) . . . . 178.7(6) no Br(1) C(3) C(2) C(23) . . . . -4(1) no Br(1) C(3) C(4) C(5) . . . . 0(1) no Br(1) C(3) C(4) C(9) . . . . -179.6(6) no Br(2) C(11) C(10) C(1) . . . . -177.1(6) no Br(2) C(11) C(10) C(9) . . . . 3(2) no Br(2) C(11) C(12) O(1) . . . . 177.7(5) no Br(2) C(11) C(12) C(13) . . . . 0(2) no Br(3) C(36) C(35) C(26) . . . . 179.7(6) no Br(3) C(36) C(35) C(34) . . . . -2(2) no Br(3) C(36) C(37) O(3) . . . . -179.6(5) no Br(3) C(36) C(37) C(38) . . . . 4(2) no Br(4) C(28) C(27) C(26) . . . . -177.9(6) no Br(4) C(28) C(27) C(48) . . . . 4(1) no Br(4) C(28) C(29) C(30) . . . . -1(1) no Br(4) C(28) C(29) C(34) . . . . 179.1(6) no O(1) C(1) C(2) C(3) . . . . -179.3(7) no O(1) C(1) C(2) C(23) . . . . 3(1) no O(1) C(1) C(10) C(9) . . . . 179.6(7) no O(1) C(1) C(10) C(11) . . . . -0.6(9) no O(1) C(12) C(11) C(10) . . . . -0(1) no O(1) C(12) C(13) C(14) . . . . 79(1) no O(1) C(12) C(13) C(22) . . . . -99.9(9) no O(2) C(14) C(13) C(12) . . . . 3(1) no O(2) C(14) C(13) C(22) . . . . -178.2(7) no O(2) C(14) C(15) C(16) . . . . 178.7(8) no O(2) C(14) C(15) C(24) . . . . -4(1) no O(3) C(26) C(27) C(28) . . . . 177.2(7) no O(3) C(26) C(27) C(48) . . . . -5(1) no O(3) C(26) C(35) C(34) . . . . -177.7(7) no O(3) C(26) C(35) C(36) . . . . 0.8(9) no O(3) C(37) C(36) C(35) . . . . 1(1) no O(3) C(37) C(38) C(39) . . . . -76(1) no O(3) C(37) C(38) C(47) . . . . 105.7(9) no O(4) C(39) C(38) C(37) . . . . 3(1) no O(4) C(39) C(38) C(47) . . . . -178.4(8) no O(4) C(39) C(40) C(41) . . . . 179.8(8) no O(4) C(39) C(40) C(49) . . . . -0(1) no O(5) C(49) C(40) C(39) . . . . 2(2) no O(5) C(49) C(40) C(41) . . . . -177(1) no O(6) C(24) C(15) C(14) . . . . 5(2) no O(6) C(24) C(15) C(16) . . . . -177.8(9) no C(1) O(1) C(12) C(11) . . . . -0.3(9) no C(1) O(1) C(12) C(13) . . . . 177.6(7) no C(1) C(2) C(3) C(4) . . . . 2(1) no C(1) C(10) C(9) C(4) . . . . -2(1) no C(1) C(10) C(9) C(8) . . . . -179.4(8) no C(1) C(10) C(11) C(12) . . . . 0.3(9) no C(2) C(1) O(1) C(12) . . . . 179.1(8) no C(2) C(1) C(10) C(9) . . . . 1(1) no C(2) C(1) C(10) C(11) . . . . -179.0(8) no C(2) C(3) C(4) C(5) . . . . 177.2(8) no C(2) C(3) C(4) C(9) . . . . -3(1) no C(3) C(2) C(1) C(10) . . . . -1(1) no C(3) C(4) C(5) C(6) . . . . -179.5(8) no C(3) C(4) C(9) C(8) . . . . -179.7(7) no C(3) C(4) C(9) C(10) . . . . 3(1) no C(4) C(3) C(2) C(23) . . . . 179.4(8) no C(4) C(5) C(6) C(7) . . . . -1(1) no C(4) C(9) C(8) C(7) . . . . -1(1) no C(4) C(9) C(10) C(11) . . . . 178.3(9) no C(5) C(4) C(9) C(8) . . . . 0(1) no C(5) C(4) C(9) C(10) . . . . -177.4(7) no C(5) C(6) C(7) C(8) . . . . 0(1) no C(6) C(5) C(4) C(9) . . . . 1(1) no C(6) C(7) C(8) C(9) . . . . 1(1) no C(7) C(8) C(9) C(10) . . . . 176.7(8) no C(8) C(9) C(10) C(11) . . . . 1(2) no C(9) C(10) C(11) C(12) . . . . -179.8(9) no C(10) C(1) O(1) C(12) . . . . 0.6(9) no C(10) C(1) C(2) C(23) . . . . -178.7(8) no C(10) C(11) C(12) C(13) . . . . -177(1) no C(11) C(12) C(13) C(14) . . . . -104(1) no C(11) C(12) C(13) C(22) . . . . 77(1) no C(12) C(13) C(14) C(15) . . . . -178.1(7) no C(12) C(13) C(22) C(17) . . . . 178.5(7) no C(12) C(13) C(22) C(21) . . . . -2(1) no C(13) C(14) C(15) C(16) . . . . -0(1) no C(13) C(14) C(15) C(24) . . . . 177.3(8) no C(13) C(22) C(17) C(16) . . . . -1(1) no C(13) C(22) C(17) C(18) . . . . 177.6(8) no C(13) C(22) C(21) C(20) . . . . -179.6(9) no C(14) C(13) C(22) C(17) . . . . -0(1) no C(14) C(13) C(22) C(21) . . . . 179.1(8) no C(14) C(15) C(16) C(17) . . . . -1(1) no C(15) C(14) C(13) C(22) . . . . 1(1) no C(15) C(16) C(17) C(18) . . . . -177.0(8) no C(15) C(16) C(17) C(22) . . . . 1(1) no C(16) C(17) C(18) C(19) . . . . 179.3(9) no C(16) C(17) C(22) C(21) . . . . 180.0(8) no C(17) C(16) C(15) C(24) . . . . -178.3(8) no C(17) C(18) C(19) C(20) . . . . 2(2) no C(17) C(22) C(21) C(20) . . . . -0(1) no C(18) C(17) C(22) C(21) . . . . -2(1) no C(18) C(19) C(20) C(21) . . . . -4(2) no C(19) C(18) C(17) C(22) . . . . 1(1) no C(19) C(20) C(21) C(22) . . . . 3(2) no C(26) O(3) C(37) C(36) . . . . -0.9(9) no C(26) O(3) C(37) C(38) . . . . 176.4(7) no C(26) C(27) C(28) C(29) . . . . -1(1) no C(26) C(35) C(34) C(29) . . . . 1(1) no C(26) C(35) C(34) C(33) . . . . -179.4(8) no C(26) C(35) C(36) C(37) . . . . -1(1) no C(27) C(26) O(3) C(37) . . . . -177.6(7) no C(27) C(26) C(35) C(34) . . . . -0(1) no C(27) C(26) C(35) C(36) . . . . 178.3(8) no C(27) C(28) C(29) C(30) . . . . -178.1(8) no C(27) C(28) C(29) C(34) . . . . 2(1) no C(28) C(27) C(26) C(35) . . . . -0(1) no C(28) C(29) C(30) C(31) . . . . -179.6(8) no C(28) C(29) C(34) C(33) . . . . 178.5(7) no C(28) C(29) C(34) C(35) . . . . -2(1) no C(29) C(28) C(27) C(48) . . . . -178.6(7) no C(29) C(30) C(31) C(32) . . . . 1(2) no C(29) C(34) C(33) C(32) . . . . 1(1) no C(29) C(34) C(35) C(36) . . . . -176.5(9) no C(30) C(29) C(34) C(33) . . . . -1(1) no C(30) C(29) C(34) C(35) . . . . 178.0(7) no C(30) C(31) C(32) C(33) . . . . -1(2) no C(31) C(30) C(29) C(34) . . . . 0(1) no C(31) C(32) C(33) C(34) . . . . -0(1) no C(32) C(33) C(34) C(35) . . . . -177.7(8) no C(33) C(34) C(35) C(36) . . . . 3(2) no C(34) C(35) C(36) C(37) . . . . 176.8(9) no C(35) C(26) O(3) C(37) . . . . -0.0(9) no C(35) C(26) C(27) C(48) . . . . 177.8(8) no C(35) C(36) C(37) C(38) . . . . -175.2(9) no C(36) C(37) C(38) C(39) . . . . 101(1) no C(36) C(37) C(38) C(47) . . . . -78(1) no C(37) C(38) C(39) C(40) . . . . -179.3(8) no C(37) C(38) C(47) C(42) . . . . 177.7(8) no C(37) C(38) C(47) C(46) . . . . -3(1) no C(38) C(39) C(40) C(41) . . . . 2(1) no C(38) C(39) C(40) C(49) . . . . -177.9(9) no C(38) C(47) C(42) C(41) . . . . 1(1) no C(38) C(47) C(42) C(43) . . . . -179.1(8) no C(38) C(47) C(46) C(45) . . . . -178.9(9) no C(39) C(38) C(47) C(42) . . . . -1(1) no C(39) C(38) C(47) C(46) . . . . 178.6(8) no C(39) C(40) C(41) C(42) . . . . -2(2) no C(40) C(39) C(38) C(47) . . . . -1(1) no C(40) C(41) C(42) C(43) . . . . -179.4(9) no C(40) C(41) C(42) C(47) . . . . 0(1) no C(41) C(42) C(43) C(44) . . . . 177.0(9) no C(41) C(42) C(47) C(46) . . . . -178.5(8) no C(42) C(41) C(40) C(49) . . . . 178.0(9) no C(42) C(43) C(44) C(45) . . . . 2(2) no C(42) C(47) C(46) C(45) . . . . 1(1) no C(43) C(42) C(47) C(46) . . . . 1(1) no C(43) C(44) C(45) C(46) . . . . 0(2) no C(44) C(43) C(42) C(47) . . . . -3(2) no C(44) C(45) C(46) C(47) . . . . -1(2) no #------------------------------------------------------------------------------ #============================================================================== # 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 #==============================================================================