# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Julien Gautrot' _publ_contact_author_email JULIENGAUTROT@YAHOO.FR _publ_section_title ; Synthesis of electron-accepting polymers containing phenanthra-9,10-quinone units ; loop_ _publ_author_name J.E.Gautrot D.C.Cupertino M.Helliwell P.Hodge J.Raftery # Attachment 'Cpd7.cif' data_s1920ba _database_code_depnum_ccdc_archive 'CCDC 701642' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H6 Br2 O2' _chemical_formula_weight 366.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.307(2) _cell_length_b 7.976(2) _cell_length_c 11.348(2) _cell_angle_alpha 73.870(3) _cell_angle_beta 77.321(4) _cell_angle_gamma 64.943(3) _cell_volume 571.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 449 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 22.83 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.127 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 7.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2252 _exptl_absorpt_correction_T_max 0.9326 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2875 _diffrn_reflns_av_R_equivalents 0.0940 _diffrn_reflns_av_sigmaI/netI 0.2881 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1987 _reflns_number_gt 858 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1987 _refine_ls_number_parameters 158 _refine_ls_number_restraints 149 _refine_ls_R_factor_all 0.1561 _refine_ls_R_factor_gt 0.0844 _refine_ls_wR_factor_ref 0.1846 _refine_ls_wR_factor_gt 0.1600 _refine_ls_goodness_of_fit_ref 0.809 _refine_ls_restrained_S_all 0.782 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.3597(3) 0.6286(2) 0.87855(16) 0.0249(5) Uani 1 1 d . . . Br2 Br 0.1712(3) 1.2293(2) -0.09713(16) 0.0258(5) Uani 1 1 d . . . O1 O 0.2481(15) 1.3004(14) 0.5540(9) 0.021(2) Uani 1 1 d U . . O2 O 0.1781(16) 1.4544(15) 0.3123(10) 0.021(3) Uiso 1 1 d U . . C1 C 0.292(2) 0.922(2) 0.6625(15) 0.020(2) Uani 1 1 d U . . H1 H 0.2961 0.9985 0.7125 0.024 Uiso 1 1 calc R . . C2 C 0.317(2) 0.738(2) 0.7141(15) 0.022(2) Uani 1 1 d U . . C3 C 0.298(2) 0.634(2) 0.6369(14) 0.017(2) Uani 1 1 d U . . H3 H 0.2994 0.5101 0.6714 0.021 Uiso 1 1 calc R . . C4 C 0.277(2) 0.707(2) 0.5167(14) 0.018(2) Uani 1 1 d U . . H4 H 0.2783 0.6287 0.4665 0.021 Uiso 1 1 calc R . . C5 C 0.243(2) 0.867(2) 0.2462(15) 0.023(2) Uani 1 1 d U . . H5 H 0.2643 0.7376 0.2785 0.028 Uiso 1 1 calc R . . C6 C 0.228(2) 0.939(2) 0.1208(15) 0.024(3) Uani 1 1 d U . . H6 H 0.2329 0.8627 0.0683 0.029 Uiso 1 1 calc R . . C7 C 0.205(3) 1.130(2) 0.0734(15) 0.026(3) Uani 1 1 d U . . C8 C 0.190(2) 1.243(2) 0.1478(15) 0.022(2) Uani 1 1 d U . . H8 H 0.1630 1.3737 0.1149 0.026 Uiso 1 1 calc R . . C9 C 0.242(2) 1.205(2) 0.4917(14) 0.019(2) Uani 1 1 d U . . C10 C 0.262(2) 1.001(2) 0.5383(15) 0.018(2) Uani 1 1 d U . . C11 C 0.255(2) 0.896(2) 0.4618(15) 0.017(2) Uani 1 1 d U . . C12 C 0.227(3) 0.982(2) 0.3281(16) 0.023(2) Uani 1 1 d U . . C13 C 0.214(2) 1.167(2) 0.2746(15) 0.020(2) Uani 1 1 d U . . C14 C 0.203(2) 1.291(2) 0.3557(15) 0.021(2) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0247(11) 0.0233(11) 0.0263(12) -0.0074(9) -0.0008(9) -0.0088(9) Br2 0.0314(12) 0.0228(11) 0.0259(12) -0.0081(9) -0.0036(9) -0.0111(10) O1 0.014(6) 0.024(5) 0.027(5) -0.015(4) 0.008(5) -0.009(5) C1 0.013(6) 0.021(5) 0.027(4) -0.008(4) -0.002(5) -0.006(5) C2 0.016(6) 0.021(5) 0.027(5) -0.005(4) 0.000(5) -0.005(5) C3 0.005(5) 0.019(5) 0.027(5) -0.004(3) 0.004(5) -0.006(5) C4 0.008(5) 0.015(4) 0.029(5) -0.004(3) -0.003(5) -0.002(5) C5 0.025(6) 0.019(5) 0.028(4) -0.007(4) -0.003(6) -0.009(5) C6 0.028(7) 0.021(5) 0.030(4) -0.006(5) -0.011(6) -0.013(6) C7 0.034(7) 0.021(5) 0.028(5) -0.005(4) -0.007(6) -0.014(6) C8 0.024(6) 0.019(5) 0.024(4) -0.006(3) 0.001(5) -0.011(5) C9 0.014(5) 0.021(4) 0.026(4) -0.008(3) 0.000(5) -0.009(5) C10 0.010(5) 0.019(4) 0.027(4) -0.006(3) -0.001(5) -0.007(4) C11 0.009(5) 0.015(4) 0.025(4) -0.006(3) 0.001(5) -0.003(4) C12 0.024(6) 0.014(4) 0.026(4) -0.006(3) -0.003(5) -0.001(5) C13 0.018(5) 0.018(4) 0.026(4) -0.005(3) -0.005(5) -0.007(5) C14 0.018(6) 0.018(4) 0.028(4) -0.007(3) -0.004(5) -0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.861(16) . ? Br2 C7 1.904(16) . ? O1 C9 1.190(15) . ? O2 C14 1.207(16) . ? C1 C2 1.37(2) . ? C1 C10 1.40(2) . ? C1 H1 0.9500 . ? C2 C3 1.423(19) . ? C3 C4 1.34(2) . ? C3 H3 0.9500 . ? C4 C11 1.417(19) . ? C4 H4 0.9500 . ? C5 C6 1.39(2) . ? C5 C12 1.430(19) . ? C5 H5 0.9500 . ? C6 C7 1.41(2) . ? C6 H6 0.9500 . ? C7 C8 1.359(19) . ? C8 C13 1.42(2) . ? C8 H8 0.9500 . ? C9 C10 1.519(19) . ? C9 C14 1.54(2) . ? C10 C11 1.386(18) . ? C11 C12 1.50(2) . ? C12 C13 1.40(2) . ? C13 C14 1.499(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 121.6(14) . . ? C2 C1 H1 119.2 . . ? C10 C1 H1 119.2 . . ? C1 C2 C3 116.7(15) . . ? C1 C2 Br1 122.5(12) . . ? C3 C2 Br1 120.7(12) . . ? C4 C3 C2 121.4(15) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C11 122.2(14) . . ? C3 C4 H4 118.9 . . ? C11 C4 H4 118.9 . . ? C6 C5 C12 122.0(15) . . ? C6 C5 H5 119.0 . . ? C12 C5 H5 119.0 . . ? C5 C6 C7 118.2(14) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C8 C7 C6 121.7(16) . . ? C8 C7 Br2 120.6(13) . . ? C6 C7 Br2 117.5(12) . . ? C7 C8 C13 119.7(15) . . ? C7 C8 H8 120.2 . . ? C13 C8 H8 120.2 . . ? O1 C9 C10 124.3(15) . . ? O1 C9 C14 119.9(14) . . ? C10 C9 C14 115.7(12) . . ? C11 C10 C1 121.4(15) . . ? C11 C10 C9 122.1(15) . . ? C1 C10 C9 116.5(12) . . ? C10 C11 C4 116.4(15) . . ? C10 C11 C12 120.6(13) . . ? C4 C11 C12 123.0(13) . . ? C13 C12 C5 116.9(16) . . ? C13 C12 C11 121.9(13) . . ? C5 C12 C11 120.5(14) . . ? C12 C13 C8 120.8(14) . . ? C12 C13 C14 119.2(15) . . ? C8 C13 C14 119.6(14) . . ? O2 C14 C13 120.0(15) . . ? O2 C14 C9 120.1(13) . . ? C13 C14 C9 119.7(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -4(2) . . . . ? C10 C1 C2 Br1 179.3(12) . . . . ? C1 C2 C3 C4 6(2) . . . . ? Br1 C2 C3 C4 -176.4(12) . . . . ? C2 C3 C4 C11 -6(2) . . . . ? C12 C5 C6 C7 3(2) . . . . ? C5 C6 C7 C8 -2(3) . . . . ? C5 C6 C7 Br2 -177.1(13) . . . . ? C6 C7 C8 C13 5(3) . . . . ? Br2 C7 C8 C13 179.7(12) . . . . ? C2 C1 C10 C11 0(2) . . . . ? C2 C1 C10 C9 -178.7(14) . . . . ? O1 C9 C10 C11 -179.9(15) . . . . ? C14 C9 C10 C11 3(2) . . . . ? O1 C9 C10 C1 -1(2) . . . . ? C14 C9 C10 C1 -178.3(14) . . . . ? C1 C10 C11 C4 0(2) . . . . ? C9 C10 C11 C4 179.4(13) . . . . ? C1 C10 C11 C12 -178.7(14) . . . . ? C9 C10 C11 C12 0(2) . . . . ? C3 C4 C11 C10 2(2) . . . . ? C3 C4 C11 C12 -178.5(14) . . . . ? C6 C5 C12 C13 -6(2) . . . . ? C6 C5 C12 C11 -176.8(14) . . . . ? C10 C11 C12 C13 2(2) . . . . ? C4 C11 C12 C13 -177.0(16) . . . . ? C10 C11 C12 C5 172.6(15) . . . . ? C4 C11 C12 C5 -6(2) . . . . ? C5 C12 C13 C8 9(2) . . . . ? C11 C12 C13 C8 179.3(15) . . . . ? C5 C12 C13 C14 -178.2(14) . . . . ? C11 C12 C13 C14 -7(2) . . . . ? C7 C8 C13 C12 -8(3) . . . . ? C7 C8 C13 C14 178.3(14) . . . . ? C12 C13 C14 O2 -174.9(16) . . . . ? C8 C13 C14 O2 -2(2) . . . . ? C12 C13 C14 C9 10(2) . . . . ? C8 C13 C14 C9 -176.3(15) . . . . ? O1 C9 C14 O2 0(2) . . . . ? C10 C9 C14 O2 177.4(14) . . . . ? O1 C9 C14 C13 174.6(13) . . . . ? C10 C9 C14 C13 -8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.259 _refine_diff_density_min -1.370 _refine_diff_density_rms 0.244 data_s1894abs _database_code_depnum_ccdc_archive 'CCDC 701643' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H6 Br2 O2' _chemical_formula_weight 366.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.683(6) _cell_length_b 7.257(4) _cell_length_c 14.885(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.542(8) _cell_angle_gamma 90.00 _cell_volume 1189.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 903 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 23.50 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 6.805 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.684 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6392 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0895 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2426 _reflns_number_gt 1711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.7544P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2426 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.81703(6) 0.85828(9) 0.05751(5) 0.02210(19) Uani 1 1 d . . . Br2 Br 0.37894(6) 0.50682(10) 0.30401(5) 0.0292(2) Uani 1 1 d . . . O1 O 0.2293(4) 0.8425(7) -0.2512(3) 0.0297(12) Uani 1 1 d . . . O2 O 0.0823(4) 0.6519(6) -0.1726(3) 0.0291(12) Uani 1 1 d . . . C1 C 0.4843(6) 0.8460(9) -0.1609(5) 0.0233(15) Uani 1 1 d . . . H1 H 0.4535 0.8766 -0.2267 0.028 Uiso 1 1 calc R . . C2 C 0.6083(6) 0.8637(9) -0.1115(4) 0.0231(15) Uani 1 1 d . . . H2 H 0.6631 0.9019 -0.1427 0.028 Uiso 1 1 calc R . . C3 C 0.6490(6) 0.8227(8) -0.0135(4) 0.0195(15) Uani 1 1 d . . . C4 C 0.5731(5) 0.7605(8) 0.0333(4) 0.0179(15) Uani 1 1 d . . . H4 H 0.6049 0.7321 0.0994 0.021 Uiso 1 1 calc R . . C5 C 0.4031(6) 0.6324(8) 0.1298(4) 0.0203(15) Uani 1 1 d . . . H5 H 0.4864 0.6466 0.1668 0.024 Uiso 1 1 calc R . . C6 C 0.3218(6) 0.5700(9) 0.1724(4) 0.0195(15) Uani 1 1 d . . . C7 C 0.1974(6) 0.5521(9) 0.1225(5) 0.0255(16) Uani 1 1 d . . . H7 H 0.1429 0.5122 0.1536 0.031 Uiso 1 1 calc R . . C8 C 0.1565(6) 0.5945(9) 0.0261(5) 0.0247(16) Uani 1 1 d . . . H8 H 0.0725 0.5831 -0.0094 0.030 Uiso 1 1 calc R . . C9 C 0.2728(6) 0.7781(9) -0.1706(5) 0.0232(16) Uani 1 1 d . . . C10 C 0.4052(5) 0.7842(8) -0.1155(4) 0.0200(15) Uani 1 1 d . . . C11 C 0.4475(5) 0.7390(8) -0.0170(4) 0.0167(14) Uani 1 1 d . . . C12 C 0.3630(5) 0.6749(8) 0.0318(4) 0.0168(14) Uani 1 1 d . . . C13 C 0.2370(5) 0.6538(9) -0.0196(4) 0.0201(15) Uani 1 1 d . . . C14 C 0.1876(6) 0.6894(9) -0.1234(5) 0.0220(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0185(3) 0.0207(3) 0.0238(4) -0.0024(3) 0.0027(3) -0.0032(3) Br2 0.0271(4) 0.0361(4) 0.0243(4) 0.0071(3) 0.0084(3) 0.0009(3) O1 0.025(3) 0.038(3) 0.016(2) -0.006(2) -0.006(2) 0.006(2) O2 0.021(2) 0.026(3) 0.032(3) -0.005(2) -0.004(2) 0.000(2) C1 0.024(3) 0.023(4) 0.022(3) 0.002(3) 0.006(3) -0.002(3) C2 0.025(4) 0.021(4) 0.023(4) 0.000(3) 0.008(3) 0.001(3) C3 0.023(3) 0.013(4) 0.021(3) -0.002(3) 0.005(3) -0.004(3) C4 0.019(3) 0.013(3) 0.016(3) 0.001(3) -0.001(3) 0.004(3) C5 0.017(3) 0.011(3) 0.029(4) -0.008(3) 0.003(3) -0.003(3) C6 0.022(3) 0.018(3) 0.018(3) 0.002(3) 0.005(3) 0.003(3) C7 0.020(4) 0.025(4) 0.031(4) -0.004(3) 0.008(3) -0.002(3) C8 0.023(4) 0.018(4) 0.031(4) -0.005(3) 0.006(3) -0.006(3) C9 0.025(4) 0.017(4) 0.023(4) -0.007(3) 0.002(3) 0.009(3) C10 0.020(3) 0.014(3) 0.018(3) -0.003(3) -0.003(3) 0.002(3) C11 0.022(3) 0.009(3) 0.016(3) -0.003(3) 0.002(3) 0.000(3) C12 0.018(3) 0.008(3) 0.019(3) -0.001(3) -0.002(3) 0.001(3) C13 0.020(3) 0.015(3) 0.023(3) 0.000(3) 0.003(3) -0.004(3) C14 0.018(3) 0.017(4) 0.022(3) -0.002(3) -0.004(3) 0.007(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C3 1.911(6) . ? Br2 C6 1.903(6) . ? O1 C9 1.228(7) . ? O2 C14 1.233(7) . ? C1 C10 1.390(9) . ? C1 C2 1.394(8) . ? C1 H1 0.9500 . ? C2 C3 1.406(9) . ? C2 H2 0.9500 . ? C3 C4 1.375(9) . ? C4 C11 1.416(8) . ? C4 H4 0.9500 . ? C5 C6 1.382(9) . ? C5 C12 1.410(8) . ? C5 H5 0.9500 . ? C6 C7 1.400(9) . ? C7 C8 1.386(9) . ? C7 H7 0.9500 . ? C8 C13 1.401(9) . ? C8 H8 0.9500 . ? C9 C10 1.489(8) . ? C9 C14 1.538(10) . ? C10 C11 1.420(8) . ? C11 C12 1.481(9) . ? C12 C13 1.423(8) . ? C13 C14 1.480(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C1 C2 121.1(6) . . ? C10 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 117.3(6) . . ? C1 C2 H2 121.3 . . ? C3 C2 H2 121.3 . . ? C4 C3 C2 123.0(6) . . ? C4 C3 Br1 118.8(4) . . ? C2 C3 Br1 118.3(5) . . ? C3 C4 C11 119.9(6) . . ? C3 C4 H4 120.1 . . ? C11 C4 H4 120.1 . . ? C6 C5 C12 120.3(5) . . ? C6 C5 H5 119.8 . . ? C12 C5 H5 119.8 . . ? C5 C6 C7 122.6(6) . . ? C5 C6 Br2 119.5(4) . . ? C7 C6 Br2 117.9(5) . . ? C8 C7 C6 117.8(7) . . ? C8 C7 H7 121.1 . . ? C6 C7 H7 121.1 . . ? C7 C8 C13 121.0(6) . . ? C7 C8 H8 119.5 . . ? C13 C8 H8 119.5 . . ? O1 C9 C10 122.7(7) . . ? O1 C9 C14 119.1(6) . . ? C10 C9 C14 118.2(6) . . ? C1 C10 C11 121.2(5) . . ? C1 C10 C9 118.6(6) . . ? C11 C10 C9 120.0(6) . . ? C4 C11 C10 117.5(6) . . ? C4 C11 C12 121.2(5) . . ? C10 C11 C12 121.3(5) . . ? C5 C12 C13 117.3(6) . . ? C5 C12 C11 122.1(5) . . ? C13 C12 C11 120.6(5) . . ? C8 C13 C12 121.0(6) . . ? C8 C13 C14 118.0(5) . . ? C12 C13 C14 120.9(6) . . ? O2 C14 C13 123.0(7) . . ? O2 C14 C9 119.4(6) . . ? C13 C14 C9 117.6(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -2.1(10) . . . . ? C1 C2 C3 C4 2.4(10) . . . . ? C1 C2 C3 Br1 -176.7(5) . . . . ? C2 C3 C4 C11 -1.3(10) . . . . ? Br1 C3 C4 C11 177.9(5) . . . . ? C12 C5 C6 C7 -2.2(10) . . . . ? C12 C5 C6 Br2 178.2(5) . . . . ? C5 C6 C7 C8 1.8(10) . . . . ? Br2 C6 C7 C8 -178.7(5) . . . . ? C6 C7 C8 C13 -0.2(10) . . . . ? C2 C1 C10 C11 0.7(10) . . . . ? C2 C1 C10 C9 176.6(6) . . . . ? O1 C9 C10 C1 -7.6(10) . . . . ? C14 C9 C10 C1 173.2(6) . . . . ? O1 C9 C10 C11 168.3(6) . . . . ? C14 C9 C10 C11 -10.8(9) . . . . ? C3 C4 C11 C10 -0.2(9) . . . . ? C3 C4 C11 C12 -179.1(6) . . . . ? C1 C10 C11 C4 0.5(9) . . . . ? C9 C10 C11 C4 -175.4(6) . . . . ? C1 C10 C11 C12 179.4(6) . . . . ? C9 C10 C11 C12 3.5(9) . . . . ? C6 C5 C12 C13 1.0(9) . . . . ? C6 C5 C12 C11 -178.9(6) . . . . ? C4 C11 C12 C5 -0.1(9) . . . . ? C10 C11 C12 C5 -178.9(6) . . . . ? C4 C11 C12 C13 -180.0(6) . . . . ? C10 C11 C12 C13 1.2(9) . . . . ? C7 C8 C13 C12 -0.9(10) . . . . ? C7 C8 C13 C14 177.6(6) . . . . ? C5 C12 C13 C8 0.5(9) . . . . ? C11 C12 C13 C8 -179.6(6) . . . . ? C5 C12 C13 C14 -178.0(6) . . . . ? C11 C12 C13 C14 2.0(9) . . . . ? C8 C13 C14 O2 -7.4(10) . . . . ? C12 C13 C14 O2 171.1(6) . . . . ? C8 C13 C14 C9 172.3(6) . . . . ? C12 C13 C14 C9 -9.2(9) . . . . ? O1 C9 C14 O2 14.0(9) . . . . ? C10 C9 C14 O2 -166.8(6) . . . . ? O1 C9 C14 C13 -165.7(6) . . . . ? C10 C9 C14 C13 13.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.635 _refine_diff_density_min -0.877 _refine_diff_density_rms 0.148