# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Min Shi' _publ_contact_author_email mshi@mail.sioc.ac.cn _publ_author_name 'Min Shi' data_mo_dm11356_0m _database_code_depnum_ccdc_archive 'CCDC 834559' #TrackingRef 'mo_dm11356_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H18 O' _chemical_formula_weight 310.37 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.066(3) _cell_length_b 11.863(3) _cell_length_c 10.534(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.516(3) _cell_angle_gamma 90.00 _cell_volume 1614.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 1854 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 29.32 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9775 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7068 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 30.03 _reflns_number_total 4154 _reflns_number_gt 3454 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0614P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3.9(18) _chemical_abaolute_configuration ad _refine_ls_number_reflns 4154 _refine_ls_number_parameters 217 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 O1 O 0.15559(12) 0.13603(14) 0.37880(16) 0.0367(4) Uani 1 1 d . . . C1 C 0.23506(15) 0.15534(16) 0.45081(19) 0.0245(4) Uani 1 1 d . . . C2 C 0.29868(14) 0.25814(16) 0.45502(18) 0.0234(4) Uani 1 1 d . . . C3 C 0.28412(16) 0.35107(17) 0.3728(2) 0.0302(5) Uani 1 1 d . . . H3 H 0.2293 0.3527 0.3026 0.036 Uiso 1 1 calc R . . C4 C 0.35184(17) 0.44033(18) 0.3968(2) 0.0361(5) Uani 1 1 d . . . H4 H 0.3446 0.5042 0.3418 0.043 Uiso 1 1 calc R . . C5 C 0.43064(17) 0.43717(18) 0.5011(3) 0.0379(5) Uani 1 1 d . . . H5 H 0.4764 0.4996 0.5163 0.046 Uiso 1 1 calc R . . C6 C 0.44449(15) 0.34476(17) 0.5841(2) 0.0302(4) Uani 1 1 d . . . H6 H 0.4982 0.3441 0.6556 0.036 Uiso 1 1 calc R . . C7 C 0.37751(13) 0.25379(15) 0.55914(17) 0.0210(4) Uani 1 1 d . . . C8 C 0.37500(13) 0.14394(14) 0.63724(17) 0.0187(3) Uani 1 1 d . . . C9 C 0.28699(14) 0.07531(15) 0.55471(18) 0.0219(4) Uani 1 1 d . . . H9 H 0.3202 0.0132 0.5112 0.026 Uiso 1 1 calc R . . C10 C 0.20848(15) 0.02203(17) 0.6303(2) 0.0272(4) Uani 1 1 d . . . H10A H 0.1512 -0.0118 0.5704 0.033 Uiso 1 1 calc R . . H10B H 0.2421 -0.0385 0.6863 0.033 Uiso 1 1 calc R . . C11 C 0.16576(15) 0.11180(18) 0.7120(2) 0.0284(4) Uani 1 1 d . . . H11A H 0.1302 0.1710 0.6556 0.034 Uiso 1 1 calc R . . H11B H 0.1145 0.0773 0.7606 0.034 Uiso 1 1 calc R . . C12 C 0.25149(14) 0.16382(15) 0.80381(18) 0.0226(4) Uani 1 1 d . . . C13 C 0.23326(17) 0.19886(16) 0.92589(19) 0.0284(4) Uani 1 1 d . . . H13 H 0.1655 0.1928 0.9476 0.034 Uiso 1 1 calc R . . C14 C 0.31141(18) 0.24183(17) 1.0148(2) 0.0324(5) Uani 1 1 d . . . H14 H 0.2977 0.2657 1.0967 0.039 Uiso 1 1 calc R . . C15 C 0.41049(18) 0.24966(18) 0.9831(2) 0.0335(5) Uani 1 1 d . . . H15 H 0.4653 0.2779 1.0441 0.040 Uiso 1 1 calc R . . C16 C 0.42979(16) 0.21658(17) 0.8629(2) 0.0284(4) Uani 1 1 d . . . H16 H 0.4979 0.2228 0.8423 0.034 Uiso 1 1 calc R . . C17 C 0.35124(14) 0.17442(14) 0.77163(18) 0.0207(4) Uani 1 1 d . . . C18 C 0.47576(13) 0.07600(14) 0.64589(17) 0.0189(3) Uani 1 1 d . . . C19 C 0.54787(15) 0.09561(16) 0.56424(19) 0.0252(4) Uani 1 1 d . . . H19 H 0.5385 0.1573 0.5062 0.030 Uiso 1 1 calc R . . C20 C 0.63415(15) 0.02584(17) 0.5662(2) 0.0287(4) Uani 1 1 d . . . H20 H 0.6829 0.0404 0.5097 0.034 Uiso 1 1 calc R . . C21 C 0.64880(15) -0.06389(17) 0.6497(2) 0.0275(4) Uani 1 1 d . . . H21 H 0.7075 -0.1114 0.6512 0.033 Uiso 1 1 calc R . . C22 C 0.57700(17) -0.08425(17) 0.7319(2) 0.0298(5) Uani 1 1 d . . . H22 H 0.5864 -0.1463 0.7895 0.036 Uiso 1 1 calc R . . C23 C 0.49164(15) -0.01463(16) 0.73029(19) 0.0277(4) Uani 1 1 d . . . H23 H 0.4434 -0.0290 0.7875 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0325(8) 0.0400(8) 0.0338(8) -0.0072(7) -0.0079(7) 0.0041(7) C1 0.0243(9) 0.0256(9) 0.0233(9) -0.0051(7) 0.0027(7) 0.0038(7) C2 0.0236(9) 0.0249(9) 0.0228(9) 0.0004(7) 0.0073(8) 0.0067(7) C3 0.0302(11) 0.0346(11) 0.0270(10) 0.0080(9) 0.0080(9) 0.0113(9) C4 0.0346(11) 0.0291(10) 0.0470(13) 0.0164(10) 0.0139(10) 0.0084(9) C5 0.0271(10) 0.0243(10) 0.0633(16) 0.0117(10) 0.0099(10) -0.0012(8) C6 0.0220(9) 0.0243(9) 0.0437(13) 0.0039(9) 0.0033(9) 0.0019(7) C7 0.0183(8) 0.0206(8) 0.0248(9) 0.0019(7) 0.0054(7) 0.0039(7) C8 0.0159(8) 0.0179(8) 0.0220(9) 0.0010(6) 0.0024(7) 0.0023(6) C9 0.0204(8) 0.0197(8) 0.0257(9) -0.0051(7) 0.0039(7) 0.0005(6) C10 0.0234(9) 0.0255(10) 0.0335(10) -0.0018(8) 0.0067(8) -0.0036(7) C11 0.0224(9) 0.0299(10) 0.0344(11) -0.0004(8) 0.0096(8) 0.0007(7) C12 0.0242(9) 0.0192(8) 0.0251(9) 0.0044(7) 0.0064(7) 0.0050(7) C13 0.0355(11) 0.0226(9) 0.0300(11) 0.0055(8) 0.0148(9) 0.0103(8) C14 0.0492(13) 0.0266(10) 0.0220(10) -0.0008(8) 0.0071(9) 0.0120(9) C15 0.0397(12) 0.0294(10) 0.0288(11) -0.0057(8) -0.0034(9) 0.0040(9) C16 0.0263(10) 0.0285(10) 0.0296(11) -0.0049(8) 0.0019(8) 0.0034(8) C17 0.0223(9) 0.0173(8) 0.0226(9) 0.0004(7) 0.0032(7) 0.0039(7) C18 0.0166(8) 0.0191(8) 0.0207(9) -0.0018(7) 0.0019(7) 0.0029(6) C19 0.0258(9) 0.0225(9) 0.0286(10) 0.0018(8) 0.0088(8) 0.0046(7) C20 0.0247(10) 0.0292(10) 0.0346(11) -0.0025(8) 0.0124(8) 0.0024(8) C21 0.0240(9) 0.0261(9) 0.0317(11) -0.0079(8) 0.0019(8) 0.0078(7) C22 0.0356(11) 0.0287(10) 0.0250(11) 0.0033(8) 0.0044(9) 0.0142(8) C23 0.0299(10) 0.0278(9) 0.0272(10) 0.0049(8) 0.0098(8) 0.0084(8) _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 O1 C1 1.214(2) . ? C1 C2 1.473(3) . ? C1 C9 1.530(3) . ? C2 C7 1.390(3) . ? C2 C3 1.397(3) . ? C3 C4 1.379(3) . ? C3 H3 0.9500 . ? C4 C5 1.391(3) . ? C4 H4 0.9500 . ? C5 C6 1.397(3) . ? C5 H5 0.9500 . ? C6 C7 1.390(3) . ? C6 H6 0.9500 . ? C7 C8 1.544(2) . ? C8 C18 1.535(2) . ? C8 C17 1.537(3) . ? C8 C9 1.564(3) . ? C9 C10 1.526(3) . ? C9 H9 1.0000 . ? C10 C11 1.526(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.500(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.400(2) . ? C12 C13 1.405(3) . ? C13 C14 1.377(3) . ? C13 H13 0.9500 . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 C17 1.391(3) . ? C16 H16 0.9500 . ? C18 C19 1.386(2) . ? C18 C23 1.391(3) . ? C19 C20 1.396(3) . ? C19 H19 0.9500 . ? C20 C21 1.376(3) . ? C20 H20 0.9500 . ? C21 C22 1.388(3) . ? C21 H21 0.9500 . ? C22 C23 1.386(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? 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 O1 C1 C2 127.01(19) . . ? O1 C1 C9 125.31(18) . . ? C2 C1 C9 107.69(16) . . ? C7 C2 C3 122.37(18) . . ? C7 C2 C1 109.99(16) . . ? C3 C2 C1 127.60(18) . . ? C4 C3 C2 117.9(2) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 121.9(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 118.1(2) . . ? C7 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C6 C7 C2 119.53(17) . . ? C6 C7 C8 128.09(17) . . ? C2 C7 C8 112.34(15) . . ? C18 C8 C17 110.95(15) . . ? C18 C8 C7 112.90(14) . . ? C17 C8 C7 108.38(14) . . ? C18 C8 C9 108.26(14) . . ? C17 C8 C9 113.73(14) . . ? C7 C8 C9 102.42(14) . . ? C10 C9 C1 111.68(16) . . ? C10 C9 C8 114.91(16) . . ? C1 C9 C8 106.65(14) . . ? C10 C9 H9 107.8 . . ? C1 C9 H9 107.8 . . ? C8 C9 H9 107.8 . . ? C11 C10 C9 109.61(16) . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 110.49(16) . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C17 C12 C13 119.02(19) . . ? C17 C12 C11 120.93(18) . . ? C13 C12 C11 120.02(18) . . ? C14 C13 C12 121.54(19) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 119.02(18) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 120.3(2) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 121.22(19) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C16 C17 C12 118.88(18) . . ? C16 C17 C8 119.48(16) . . ? C12 C17 C8 121.62(17) . . ? C19 C18 C23 118.40(16) . . ? C19 C18 C8 122.07(16) . . ? C23 C18 C8 119.29(16) . . ? C18 C19 C20 120.85(18) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C21 C20 C19 120.23(19) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 119.35(18) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 120.38(18) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C18 120.78(18) . . ? C22 C23 H23 119.6 . . ? C18 C23 H23 119.6 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.210 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.048 data_dm11379 _database_code_depnum_ccdc_archive 'CCDC 837266' #TrackingRef 'dm11379.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 O' _chemical_formula_weight 262.33 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.653(3) _cell_length_b 7.9432(18) _cell_length_c 23.492(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2734.4(11) _cell_formula_units_Z 8 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 1916 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 23.78 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9848 _exptl_absorpt_correction_T_max 0.9962 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17150 _diffrn_reflns_av_R_equivalents 0.1099 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2685 _reflns_number_gt 1810 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0717P)^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 2685 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.002 _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 O1 O 0.36091(11) 0.1686(2) 0.51603(8) 0.0320(5) Uani 1 1 d . . . C1 C 0.39715(16) 0.2857(3) 0.54099(9) 0.0209(6) Uani 1 1 d . . . C2 C 0.49553(15) 0.3062(3) 0.55208(9) 0.0177(6) Uani 1 1 d . . . C3 C 0.56702(16) 0.1993(3) 0.53706(9) 0.0225(6) Uani 1 1 d . . . H3 H 0.5558 0.0979 0.5168 0.027 Uiso 1 1 calc R . . C4 C 0.65441(15) 0.2447(3) 0.55226(10) 0.0234(6) Uani 1 1 d . . . H4 H 0.7044 0.1747 0.5421 0.028 Uiso 1 1 calc R . . C5 C 0.66963(16) 0.3926(3) 0.58243(9) 0.0240(6) Uani 1 1 d . . . H5 H 0.7303 0.4220 0.5926 0.029 Uiso 1 1 calc R . . C6 C 0.59885(15) 0.4979(3) 0.59803(9) 0.0214(6) Uani 1 1 d . . . H6 H 0.6102 0.5972 0.6194 0.026 Uiso 1 1 calc R . . C7 C 0.51026(15) 0.4551(3) 0.58166(9) 0.0172(5) Uani 1 1 d . . . C8 C 0.42192(14) 0.5538(3) 0.59056(9) 0.0173(5) Uani 1 1 d . . . H8 H 0.4239 0.6559 0.5657 0.021 Uiso 1 1 calc R . . C9 C 0.34653(15) 0.4339(3) 0.56726(9) 0.0189(6) Uani 1 1 d . . . H9 H 0.3116 0.4936 0.5367 0.023 Uiso 1 1 calc R . . C10 C 0.27995(15) 0.3731(3) 0.61280(10) 0.0228(6) Uani 1 1 d . . . H10A H 0.2499 0.2683 0.5998 0.027 Uiso 1 1 calc R . . H10B H 0.2321 0.4592 0.6188 0.027 Uiso 1 1 calc R . . C11 C 0.32964(16) 0.3399(3) 0.66899(10) 0.0233(6) Uani 1 1 d . . . H11A H 0.2864 0.2930 0.6972 0.028 Uiso 1 1 calc R . . H11B H 0.3790 0.2567 0.6629 0.028 Uiso 1 1 calc R . . C12 C 0.36943(15) 0.5026(3) 0.69107(9) 0.0192(5) Uani 1 1 d . . . C13 C 0.36300(15) 0.5496(3) 0.74850(10) 0.0231(6) Uani 1 1 d . . . C14 C 0.39649(15) 0.7051(3) 0.76473(10) 0.0265(6) Uani 1 1 d . . . H14 H 0.3939 0.7370 0.8037 0.032 Uiso 1 1 calc R . . C15 C 0.43375(16) 0.8153(3) 0.72541(11) 0.0252(6) Uani 1 1 d . . . H15 H 0.4548 0.9224 0.7376 0.030 Uiso 1 1 calc R . . C16 C 0.44073(15) 0.7712(3) 0.66833(10) 0.0208(6) Uani 1 1 d . . . C17 C 0.40995(14) 0.6117(3) 0.65179(9) 0.0167(5) Uani 1 1 d . . . C18 C 0.47782(16) 0.8976(3) 0.62616(11) 0.0253(6) Uani 1 1 d . . . H18A H 0.4974 0.9992 0.6464 0.038 Uiso 1 1 calc R . . H18B H 0.4301 0.9270 0.5987 0.038 Uiso 1 1 calc R . . H18C H 0.5300 0.8487 0.6060 0.038 Uiso 1 1 calc R . . C19 C 0.31963(18) 0.4353(4) 0.79200(10) 0.0386(8) Uani 1 1 d . . . H19A H 0.3263 0.4849 0.8300 0.058 Uiso 1 1 calc R . . H19B H 0.3498 0.3252 0.7911 0.058 Uiso 1 1 calc R . . H19C H 0.2547 0.4216 0.7832 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0284(10) 0.0273(12) 0.0404(10) -0.0138(9) -0.0069(8) -0.0018(8) C1 0.0236(12) 0.0229(16) 0.0162(11) 0.0001(11) -0.0018(10) -0.0019(11) C2 0.0212(12) 0.0186(16) 0.0132(10) 0.0012(10) 0.0009(9) -0.0012(10) C3 0.0300(13) 0.0199(16) 0.0175(11) 0.0015(10) 0.0036(10) 0.0012(11) C4 0.0213(12) 0.0273(17) 0.0216(12) 0.0077(11) 0.0060(9) 0.0076(11) C5 0.0194(11) 0.0327(17) 0.0200(12) 0.0032(11) -0.0007(10) -0.0031(11) C6 0.0227(12) 0.0233(16) 0.0183(11) -0.0007(11) 0.0001(9) -0.0038(11) C7 0.0224(12) 0.0176(15) 0.0117(11) 0.0025(10) 0.0028(9) -0.0012(10) C8 0.0189(11) 0.0158(14) 0.0171(11) 0.0016(10) -0.0001(9) 0.0009(9) C9 0.0199(12) 0.0193(15) 0.0174(11) 0.0004(10) -0.0036(9) 0.0010(10) C10 0.0172(11) 0.0210(16) 0.0303(14) -0.0021(11) 0.0010(10) -0.0030(10) C11 0.0229(12) 0.0215(16) 0.0255(13) 0.0059(11) 0.0062(10) -0.0013(11) C12 0.0145(11) 0.0221(15) 0.0212(12) 0.0030(10) -0.0011(9) 0.0036(10) C13 0.0148(11) 0.0347(17) 0.0199(11) 0.0006(11) -0.0010(9) 0.0020(11) C14 0.0208(12) 0.0416(19) 0.0171(12) -0.0079(12) -0.0012(10) 0.0054(12) C15 0.0218(12) 0.0230(16) 0.0310(13) -0.0106(11) -0.0036(10) 0.0032(11) C16 0.0176(11) 0.0203(16) 0.0245(12) -0.0004(11) -0.0015(9) 0.0010(11) C17 0.0141(10) 0.0178(15) 0.0181(11) 0.0005(10) -0.0020(9) 0.0035(10) C18 0.0267(12) 0.0168(16) 0.0325(13) -0.0014(11) -0.0023(11) -0.0005(11) C19 0.0298(14) 0.065(2) 0.0214(13) 0.0036(13) 0.0022(11) -0.0124(14) _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 O1 C1 1.221(3) . ? C1 C2 1.474(3) . ? C1 C9 1.522(3) . ? C2 C7 1.389(3) . ? C2 C3 1.394(3) . ? C3 C4 1.377(3) . ? C3 H3 0.9500 . ? C4 C5 1.390(4) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 C7 1.396(3) . ? C6 H6 0.9500 . ? C7 C8 1.528(3) . ? C8 C17 1.520(3) . ? C8 C9 1.558(3) . ? C8 H8 1.0000 . ? C9 C10 1.527(3) . ? C9 H9 1.0000 . ? C10 C11 1.530(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.510(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.398(3) . ? C12 C13 1.403(3) . ? C13 C14 1.382(4) . ? C13 C19 1.507(4) . ? C14 C15 1.385(4) . ? C14 H14 0.9500 . ? C15 C16 1.389(3) . ? C15 H15 0.9500 . ? C16 C17 1.400(3) . ? C16 C18 1.512(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 O1 C1 C2 126.5(2) . . ? O1 C1 C9 124.9(2) . . ? C2 C1 C9 108.6(2) . . ? C7 C2 C3 121.9(2) . . ? C7 C2 C1 109.5(2) . . ? C3 C2 C1 128.6(2) . . ? C4 C3 C2 118.3(2) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 121.8(2) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C7 118.5(2) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C2 C7 C6 119.3(2) . . ? C2 C7 C8 111.95(19) . . ? C6 C7 C8 128.7(2) . . ? C17 C8 C7 112.48(17) . . ? C17 C8 C9 115.82(18) . . ? C7 C8 C9 103.84(19) . . ? C17 C8 H8 108.1 . . ? C7 C8 H8 108.1 . . ? C9 C8 H8 108.1 . . ? C1 C9 C10 110.5(2) . . ? C1 C9 C8 105.65(18) . . ? C10 C9 C8 113.60(18) . . ? C1 C9 H9 109.0 . . ? C10 C9 H9 109.0 . . ? C8 C9 H9 109.0 . . ? C9 C10 C11 110.79(18) . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 109.4(2) . . ? C12 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? C12 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? C17 C12 C13 119.9(2) . . ? C17 C12 C11 117.9(2) . . ? C13 C12 C11 122.2(2) . . ? C14 C13 C12 118.6(2) . . ? C14 C13 C19 120.0(2) . . ? C12 C13 C19 121.3(2) . . ? C13 C14 C15 121.4(2) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C14 C15 C16 120.9(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C17 118.2(2) . . ? C15 C16 C18 119.4(2) . . ? C17 C16 C18 122.3(2) . . ? C12 C17 C16 121.0(2) . . ? C12 C17 C8 119.1(2) . . ? C16 C17 C8 120.0(2) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C13 C19 H19A 109.5 . . ? C13 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C13 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.229 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.049 data_cd211380 _database_code_depnum_ccdc_archive 'CCDC 844935' #TrackingRef 'cd211380.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H11 Br O' _chemical_formula_weight 311.17 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4862(9) _cell_length_b 21.575(2) _cell_length_c 6.9770(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.788(2) _cell_angle_gamma 90.00 _cell_volume 1276.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2589 _cell_measurement_theta_min 4.802 _cell_measurement_theta_max 50.963 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.315 _exptl_crystal_size_mid 0.203 _exptl_crystal_size_min 0.186 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 3.206 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.24409 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 6876 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2501 _reflns_number_gt 2065 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0436P)^2^+0.4649P] 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 SHELXL _refine_ls_extinction_coef 0.0049(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2501 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0883 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _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 0.45059(4) 0.582814(14) 0.37746(5) 0.07119(16) Uani 1 1 d . . . O1 O -0.16857(19) 0.69763(8) 0.3014(3) 0.0541(5) Uani 1 1 d . . . C1 C 0.1117(3) 0.71801(10) 0.3332(3) 0.0378(5) Uani 1 1 d . . . C2 C 0.1823(3) 0.66110(11) 0.3441(3) 0.0426(5) Uani 1 1 d . . . H2 H 0.1236 0.6247 0.3435 0.051 Uiso 1 1 calc R . . C3 C 0.3459(3) 0.66026(11) 0.3561(3) 0.0458(6) Uani 1 1 d . . . C4 C 0.4332(3) 0.71364(13) 0.3531(4) 0.0504(6) Uani 1 1 d . . . H4 H 0.5427 0.7114 0.3583 0.060 Uiso 1 1 calc R . . C5 C 0.3595(3) 0.77089(12) 0.3423(4) 0.0455(6) Uani 1 1 d . . . H5 H 0.4187 0.8071 0.3397 0.055 Uiso 1 1 calc R . . C6 C 0.1969(2) 0.77329(10) 0.3354(3) 0.0360(5) Uani 1 1 d . . . C7 C 0.0810(3) 0.82534(10) 0.3226(3) 0.0365(5) Uani 1 1 d . . . C8 C -0.0663(3) 0.80171(11) 0.3088(3) 0.0394(5) Uani 1 1 d . . . C9 C -0.0596(3) 0.73395(11) 0.3136(3) 0.0395(5) Uani 1 1 d . . . C10 C -0.2102(3) 0.84127(11) 0.2942(4) 0.0497(6) Uani 1 1 d . . . H10A H -0.2462 0.8508 0.4214 0.060 Uiso 1 1 calc R . . H10B H -0.2939 0.8193 0.2248 0.060 Uiso 1 1 calc R . . C11 C -0.1710(3) 0.90101(12) 0.1890(4) 0.0547(7) Uani 1 1 d . . . H11A H -0.1666 0.8923 0.0529 0.066 Uiso 1 1 calc R . . H11B H -0.2551 0.9307 0.2069 0.066 Uiso 1 1 calc R . . C12 C -0.0176(3) 0.92958(11) 0.2556(3) 0.0449(6) Uani 1 1 d . . . C13 C 0.1089(3) 0.89196(11) 0.3203(3) 0.0411(5) Uani 1 1 d . . . C14 C 0.2493(3) 0.92006(12) 0.3803(4) 0.0523(6) Uani 1 1 d . . . H14 H 0.3324 0.8958 0.4275 0.063 Uiso 1 1 calc R . . C15 C 0.2668(4) 0.98341(13) 0.3706(4) 0.0606(7) Uani 1 1 d . . . H15 H 0.3617 1.0015 0.4106 0.073 Uiso 1 1 calc R . . C16 C 0.1456(4) 1.01986(13) 0.3024(4) 0.0613(7) Uani 1 1 d . . . H16 H 0.1584 1.0626 0.2944 0.074 Uiso 1 1 calc R . . C17 C 0.0049(4) 0.99295(12) 0.2459(4) 0.0563(7) Uani 1 1 d . . . H17 H -0.0771 1.0180 0.2001 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0626(2) 0.0625(2) 0.0874(3) -0.00655(15) -0.01435(16) 0.02839(14) O1 0.0352(9) 0.0468(10) 0.0799(13) 0.0021(9) -0.0045(8) -0.0086(7) C1 0.0322(11) 0.0432(13) 0.0378(12) 0.0009(9) -0.0009(9) 0.0004(9) C2 0.0403(13) 0.0408(13) 0.0466(13) -0.0014(10) -0.0022(10) 0.0016(10) C3 0.0422(13) 0.0485(14) 0.0462(14) -0.0032(10) -0.0042(10) 0.0133(11) C4 0.0310(12) 0.0660(17) 0.0540(15) -0.0004(12) -0.0011(11) 0.0050(11) C5 0.0316(12) 0.0536(15) 0.0513(14) 0.0020(11) 0.0006(10) -0.0036(10) C6 0.0307(11) 0.0414(12) 0.0358(11) 0.0017(9) -0.0009(9) -0.0017(9) C7 0.0347(12) 0.0402(12) 0.0345(12) 0.0031(9) -0.0014(9) -0.0014(9) C8 0.0334(12) 0.0414(12) 0.0433(13) 0.0021(9) -0.0013(9) 0.0010(9) C9 0.0310(11) 0.0440(13) 0.0434(13) 0.0017(10) 0.0006(9) -0.0025(9) C10 0.0338(12) 0.0504(15) 0.0647(16) -0.0009(12) -0.0026(11) 0.0056(10) C11 0.0507(15) 0.0485(15) 0.0641(17) -0.0002(12) -0.0128(13) 0.0109(12) C12 0.0519(14) 0.0418(13) 0.0405(13) -0.0002(10) -0.0037(11) 0.0031(10) C13 0.0442(13) 0.0404(12) 0.0386(12) 0.0024(10) -0.0002(10) -0.0039(10) C14 0.0483(15) 0.0509(15) 0.0573(16) 0.0057(11) -0.0029(12) -0.0092(11) C15 0.0661(18) 0.0537(16) 0.0616(17) 0.0022(13) -0.0018(14) -0.0231(14) C16 0.088(2) 0.0393(14) 0.0563(16) 0.0045(12) 0.0032(15) -0.0107(14) C17 0.0743(19) 0.0419(14) 0.0524(16) 0.0026(11) -0.0029(13) 0.0061(13) _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 1.896(2) . ? O1 C9 1.213(3) . ? C1 C2 1.367(3) . ? C1 C6 1.395(3) . ? C1 C9 1.496(3) . ? C2 C3 1.389(3) . ? C2 H2 0.9300 . ? C3 C4 1.370(4) . ? C4 C5 1.385(4) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 C7 1.494(3) . ? C7 C8 1.351(3) . ? C7 C13 1.457(3) . ? C8 C9 1.463(3) . ? C8 C10 1.491(3) . ? C10 C11 1.525(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.501(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.382(3) . ? C12 C13 1.408(3) . ? C13 C14 1.390(3) . ? C14 C15 1.377(4) . ? C14 H14 0.9300 . ? C15 C16 1.368(4) . ? C15 H15 0.9300 . ? C16 C17 1.374(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? 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 C6 122.8(2) . . ? C2 C1 C9 129.4(2) . . ? C6 C1 C9 107.85(19) . . ? C1 C2 C3 116.8(2) . . ? C1 C2 H2 121.6 . . ? C3 C2 H2 121.6 . . ? C4 C3 C2 121.9(2) . . ? C4 C3 Br1 119.34(18) . . ? C2 C3 Br1 118.76(19) . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 119.0(2) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C1 119.1(2) . . ? C5 C6 C7 133.3(2) . . ? C1 C6 C7 107.59(18) . . ? C8 C7 C13 121.5(2) . . ? C8 C7 C6 109.05(19) . . ? C13 C7 C6 129.5(2) . . ? C7 C8 C9 109.9(2) . . ? C7 C8 C10 122.9(2) . . ? C9 C8 C10 127.2(2) . . ? O1 C9 C8 127.9(2) . . ? O1 C9 C1 126.5(2) . . ? C8 C9 C1 105.58(18) . . ? C8 C10 C11 109.0(2) . . ? C8 C10 H10A 109.9 . . ? C11 C10 H10A 109.9 . . ? C8 C10 H10B 109.9 . . ? C11 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? C12 C11 C10 113.5(2) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C17 C12 C13 118.7(2) . . ? C17 C12 C11 120.7(2) . . ? C13 C12 C11 120.5(2) . . ? C14 C13 C12 118.9(2) . . ? C14 C13 C7 124.4(2) . . ? C12 C13 C7 116.7(2) . . ? C15 C14 C13 120.7(3) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C16 C15 C14 120.4(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.6(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C12 121.6(3) . . ? C16 C17 H17 119.2 . . ? C12 C17 H17 119.2 . . ? 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 C6 C1 C2 C3 -0.6(3) . . . . ? C9 C1 C2 C3 178.1(2) . . . . ? C1 C2 C3 C4 -1.4(4) . . . . ? C1 C2 C3 Br1 178.60(17) . . . . ? C2 C3 C4 C5 1.6(4) . . . . ? Br1 C3 C4 C5 -178.42(18) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? C4 C5 C6 C1 -2.1(3) . . . . ? C4 C5 C6 C7 -179.6(2) . . . . ? C2 C1 C6 C5 2.3(3) . . . . ? C9 C1 C6 C5 -176.6(2) . . . . ? C2 C1 C6 C7 -179.6(2) . . . . ? C9 C1 C6 C7 1.5(2) . . . . ? C5 C6 C7 C8 176.4(2) . . . . ? C1 C6 C7 C8 -1.4(3) . . . . ? C5 C6 C7 C13 -2.6(4) . . . . ? C1 C6 C7 C13 179.7(2) . . . . ? C13 C7 C8 C9 179.67(19) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C13 C7 C8 C10 -1.2(4) . . . . ? C6 C7 C8 C10 179.8(2) . . . . ? C7 C8 C9 O1 -178.7(2) . . . . ? C10 C8 C9 O1 2.2(4) . . . . ? C7 C8 C9 C1 0.2(3) . . . . ? C10 C8 C9 C1 -178.9(2) . . . . ? C2 C1 C9 O1 -1.0(4) . . . . ? C6 C1 C9 O1 177.8(2) . . . . ? C2 C1 C9 C8 -179.9(2) . . . . ? C6 C1 C9 C8 -1.1(2) . . . . ? C7 C8 C10 C11 31.4(3) . . . . ? C9 C8 C10 C11 -149.6(2) . . . . ? C8 C10 C11 C12 -44.7(3) . . . . ? C10 C11 C12 C17 -150.8(2) . . . . ? C10 C11 C12 C13 32.3(3) . . . . ? C17 C12 C13 C14 2.9(4) . . . . ? C11 C12 C13 C14 179.8(2) . . . . ? C17 C12 C13 C7 -178.2(2) . . . . ? C11 C12 C13 C7 -1.3(3) . . . . ? C8 C7 C13 C14 163.3(2) . . . . ? C6 C7 C13 C14 -17.9(4) . . . . ? C8 C7 C13 C12 -15.6(3) . . . . ? C6 C7 C13 C12 163.3(2) . . . . ? C12 C13 C14 C15 -2.2(4) . . . . ? C7 C13 C14 C15 178.9(2) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C14 C15 C16 C17 0.9(4) . . . . ? C15 C16 C17 C12 -0.2(4) . . . . ? C13 C12 C17 C16 -1.7(4) . . . . ? C11 C12 C17 C16 -178.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C4 H4 O1 0.93 2.51 3.427(3) 168.0 1_655 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.383 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.057 data_cd211424 _database_code_depnum_ccdc_archive 'CCDC 848746' #TrackingRef 'cd211424.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H20 O' _chemical_formula_weight 324.40 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.997(2) _cell_length_b 8.7960(19) _cell_length_c 20.266(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.471(4) _cell_angle_gamma 90.00 _cell_volume 1757.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2712 _cell_measurement_theta_min 5.060 _cell_measurement_theta_max 47.378 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.269 _exptl_crystal_size_mid 0.213 _exptl_crystal_size_min 0.157 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.72146 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 9277 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3442 _reflns_number_gt 2669 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0555P)^2^+0.2485P] 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 3442 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _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 O1 O -0.12979(11) 0.83434(18) 0.39533(7) 0.0901(5) Uani 1 1 d . . . C1 C -0.00967(15) 0.86222(19) 0.40652(8) 0.0575(4) Uani 1 1 d . . . C2 C 0.08852(14) 0.80965(17) 0.46331(7) 0.0503(4) Uani 1 1 d . . . C3 C 0.06630(17) 0.71615(19) 0.51570(8) 0.0606(4) Uani 1 1 d . . . H3 H -0.0208 0.6822 0.5182 0.073 Uiso 1 1 calc R . . C4 C 0.17279(18) 0.67403(18) 0.56361(8) 0.0603(4) Uani 1 1 d . . . C5 C 0.30154(18) 0.72867(18) 0.55789(8) 0.0598(4) Uani 1 1 d . . . H5 H 0.3745 0.7022 0.5905 0.072 Uiso 1 1 calc R . . C6 C 0.32460(15) 0.82029(17) 0.50577(7) 0.0522(4) Uani 1 1 d . . . H6 H 0.4118 0.8536 0.5031 0.063 Uiso 1 1 calc R . . C7 C 0.21639(13) 0.86217(15) 0.45744(7) 0.0434(3) Uani 1 1 d . . . C8 C 0.21749(13) 0.95599(15) 0.39400(6) 0.0422(3) Uani 1 1 d . . . C9 C 0.06392(14) 0.95708(16) 0.36138(7) 0.0495(4) Uani 1 1 d . . . H9 H 0.0308 1.0618 0.3621 0.059 Uiso 1 1 calc R . . C10 C 0.03362(16) 0.90063(19) 0.29023(8) 0.0596(4) Uani 1 1 d . . . H10A H -0.0633 0.8862 0.2773 0.072 Uiso 1 1 calc R . . H10B H 0.0630 0.9755 0.2605 0.072 Uiso 1 1 calc R . . C11 C 0.10598(17) 0.75235(18) 0.28391(8) 0.0630(4) Uani 1 1 d . . . H11A H 0.0770 0.6777 0.3139 0.076 Uiso 1 1 calc R . . H11B H 0.0828 0.7144 0.2385 0.076 Uiso 1 1 calc R . . C12 C 0.25604(16) 0.77413(16) 0.30079(7) 0.0508(4) Uani 1 1 d . . . C13 C 0.3441(2) 0.69894(19) 0.26548(8) 0.0673(5) Uani 1 1 d . . . H13 H 0.3086 0.6338 0.2308 0.081 Uiso 1 1 calc R . . C14 C 0.4811(2) 0.7181(2) 0.28023(10) 0.0791(6) Uani 1 1 d . . . H14 H 0.5382 0.6644 0.2567 0.095 Uiso 1 1 calc R . . C15 C 0.53396(19) 0.8169(2) 0.32984(10) 0.0778(5) Uani 1 1 d . . . H15 H 0.6273 0.8311 0.3400 0.093 Uiso 1 1 calc R . . C16 C 0.44857(15) 0.8958(2) 0.36492(8) 0.0614(4) Uani 1 1 d . . . H16 H 0.4851 0.9639 0.3981 0.074 Uiso 1 1 calc R . . C17 C 0.30938(14) 0.87471(15) 0.35127(7) 0.0455(3) Uani 1 1 d . . . C18 C 0.26395(14) 1.12075(15) 0.40748(7) 0.0476(3) Uani 1 1 d . . . C19 C 0.27543(19) 1.21296(19) 0.35313(9) 0.0710(5) Uani 1 1 d . . . H19 H 0.2599 1.1717 0.3103 0.085 Uiso 1 1 calc R . . C20 C 0.3092(2) 1.3637(2) 0.36127(12) 0.0874(6) Uani 1 1 d . . . H20 H 0.3162 1.4235 0.3241 0.105 Uiso 1 1 calc R . . C21 C 0.3327(2) 1.4263(2) 0.42407(12) 0.0846(6) Uani 1 1 d . . . H21 H 0.3555 1.5285 0.4297 0.102 Uiso 1 1 calc R . . C22 C 0.32243(18) 1.3374(2) 0.47834(11) 0.0732(5) Uani 1 1 d . . . H22 H 0.3390 1.3792 0.5211 0.088 Uiso 1 1 calc R . . C23 C 0.28750(15) 1.18529(17) 0.47003(8) 0.0558(4) Uani 1 1 d . . . H23 H 0.2799 1.1262 0.5073 0.067 Uiso 1 1 calc R . . C24 C 0.1539(2) 0.5681(2) 0.61976(9) 0.0905(6) Uani 1 1 d . . . H24A H 0.0642 0.5806 0.6302 0.136 Uiso 1 1 calc R . . H24B H 0.2196 0.5914 0.6586 0.136 Uiso 1 1 calc R . . H24C H 0.1658 0.4650 0.6063 0.136 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0406(7) 0.1432(13) 0.0855(9) 0.0142(9) 0.0069(6) -0.0161(7) C1 0.0408(8) 0.0748(10) 0.0573(9) -0.0025(8) 0.0088(7) -0.0035(7) C2 0.0464(8) 0.0574(8) 0.0486(8) -0.0030(7) 0.0125(6) -0.0051(7) C3 0.0614(10) 0.0691(10) 0.0556(9) -0.0024(8) 0.0219(8) -0.0125(8) C4 0.0813(12) 0.0571(9) 0.0448(8) -0.0017(7) 0.0169(8) -0.0053(8) C5 0.0693(11) 0.0596(9) 0.0479(8) 0.0012(7) 0.0019(7) 0.0033(8) C6 0.0488(8) 0.0542(8) 0.0520(8) -0.0003(7) 0.0039(6) -0.0021(7) C7 0.0434(8) 0.0425(7) 0.0445(7) -0.0044(6) 0.0080(6) -0.0011(6) C8 0.0398(7) 0.0432(7) 0.0436(7) -0.0012(6) 0.0065(6) -0.0009(5) C9 0.0427(8) 0.0502(8) 0.0542(8) 0.0011(6) 0.0036(6) 0.0034(6) C10 0.0528(9) 0.0698(10) 0.0527(9) 0.0039(8) -0.0021(7) -0.0042(8) C11 0.0780(12) 0.0580(9) 0.0526(9) -0.0096(7) 0.0095(8) -0.0147(8) C12 0.0655(10) 0.0415(7) 0.0473(8) 0.0044(6) 0.0151(7) -0.0002(6) C13 0.0955(14) 0.0533(9) 0.0583(10) -0.0026(8) 0.0275(9) 0.0065(9) C14 0.0868(14) 0.0811(13) 0.0784(13) 0.0032(10) 0.0407(11) 0.0229(11) C15 0.0554(10) 0.0991(14) 0.0846(13) 0.0107(12) 0.0284(9) 0.0133(10) C16 0.0487(9) 0.0761(11) 0.0609(9) -0.0003(8) 0.0133(7) 0.0012(8) C17 0.0477(8) 0.0449(7) 0.0454(7) 0.0047(6) 0.0118(6) 0.0021(6) C18 0.0417(8) 0.0444(8) 0.0575(8) -0.0015(6) 0.0107(6) -0.0002(6) C19 0.0922(14) 0.0538(10) 0.0674(11) 0.0054(8) 0.0141(9) -0.0115(9) C20 0.1101(17) 0.0529(11) 0.1006(16) 0.0142(11) 0.0211(12) -0.0121(10) C21 0.0831(14) 0.0426(9) 0.1279(19) -0.0087(11) 0.0169(12) -0.0064(9) C22 0.0719(12) 0.0555(10) 0.0923(13) -0.0251(10) 0.0138(10) -0.0006(8) C23 0.0520(9) 0.0516(9) 0.0650(10) -0.0096(7) 0.0131(7) 0.0007(7) C24 0.1282(18) 0.0891(14) 0.0574(11) 0.0106(10) 0.0250(11) -0.0163(12) _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 O1 C1 1.2100(18) . ? C1 C2 1.460(2) . ? C1 C9 1.515(2) . ? C2 C7 1.3826(19) . ? C2 C3 1.389(2) . ? C3 C4 1.369(2) . ? C3 H3 0.9300 . ? C4 C5 1.397(2) . ? C4 C24 1.506(2) . ? C5 C6 1.378(2) . ? C5 H5 0.9300 . ? C6 C7 1.3844(19) . ? C6 H6 0.9300 . ? C7 C8 1.5294(18) . ? C8 C18 1.5326(19) . ? C8 C17 1.5385(19) . ? C8 C9 1.5685(18) . ? C9 C10 1.508(2) . ? C9 H9 0.9800 . ? C10 C11 1.507(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.495(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.390(2) . ? C12 C17 1.391(2) . ? C13 C14 1.364(3) . ? C13 H13 0.9300 . ? C14 C15 1.368(3) . ? C14 H14 0.9300 . ? C15 C16 1.384(2) . ? C15 H15 0.9300 . ? C16 C17 1.386(2) . ? C16 H16 0.9300 . ? C18 C23 1.374(2) . ? C18 C19 1.388(2) . ? C19 C20 1.371(2) . ? C19 H19 0.9300 . ? C20 C21 1.371(3) . ? C20 H20 0.9300 . ? C21 C22 1.367(3) . ? C21 H21 0.9300 . ? C22 C23 1.386(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 O1 C1 C2 126.99(15) . . ? O1 C1 C9 124.32(14) . . ? C2 C1 C9 108.68(12) . . ? C7 C2 C3 122.00(14) . . ? C7 C2 C1 109.74(13) . . ? C3 C2 C1 128.22(14) . . ? C4 C3 C2 119.92(15) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 117.91(15) . . ? C3 C4 C24 121.57(17) . . ? C5 C4 C24 120.49(16) . . ? C6 C5 C4 122.52(15) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C5 C6 C7 119.22(14) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C2 C7 C6 118.43(13) . . ? C2 C7 C8 112.79(12) . . ? C6 C7 C8 128.71(13) . . ? C7 C8 C18 113.85(11) . . ? C7 C8 C17 108.07(10) . . ? C18 C8 C17 110.38(11) . . ? C7 C8 C9 102.46(10) . . ? C18 C8 C9 108.43(11) . . ? C17 C8 C9 113.53(11) . . ? C10 C9 C1 110.79(12) . . ? C10 C9 C8 115.45(12) . . ? C1 C9 C8 106.31(11) . . ? C10 C9 H9 108.0 . . ? C1 C9 H9 108.0 . . ? C8 C9 H9 108.0 . . ? C11 C10 C9 110.03(12) . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 110.32(13) . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C13 C12 C17 118.86(15) . . ? C13 C12 C11 121.20(15) . . ? C17 C12 C11 119.91(13) . . ? C14 C13 C12 121.81(17) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C15 119.47(16) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 120.01(18) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 120.96(17) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C12 118.87(13) . . ? C16 C17 C8 119.90(12) . . ? C12 C17 C8 121.16(12) . . ? C23 C18 C19 117.84(14) . . ? C23 C18 C8 123.79(13) . . ? C19 C18 C8 118.26(13) . . ? C20 C19 C18 121.37(18) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 120.07(19) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C20 119.54(17) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C23 120.35(18) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C18 C23 C22 120.83(16) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C4 C24 H24A 109.5 . . ? C4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 O1 C1 C2 C7 178.33(17) . . . . ? C9 C1 C2 C7 -0.38(17) . . . . ? O1 C1 C2 C3 0.8(3) . . . . ? C9 C1 C2 C3 -177.90(15) . . . . ? C7 C2 C3 C4 0.3(2) . . . . ? C1 C2 C3 C4 177.54(15) . . . . ? C2 C3 C4 C5 0.4(2) . . . . ? C2 C3 C4 C24 -177.67(16) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? C24 C4 C5 C6 177.08(16) . . . . ? C4 C5 C6 C7 0.9(2) . . . . ? C3 C2 C7 C6 -0.4(2) . . . . ? C1 C2 C7 C6 -178.10(13) . . . . ? C3 C2 C7 C8 176.90(13) . . . . ? C1 C2 C7 C8 -0.80(17) . . . . ? C5 C6 C7 C2 -0.2(2) . . . . ? C5 C6 C7 C8 -177.01(13) . . . . ? C2 C7 C8 C18 118.42(13) . . . . ? C6 C7 C8 C18 -64.62(18) . . . . ? C2 C7 C8 C17 -118.57(13) . . . . ? C6 C7 C8 C17 58.39(17) . . . . ? C2 C7 C8 C9 1.57(15) . . . . ? C6 C7 C8 C9 178.53(14) . . . . ? O1 C1 C9 C10 -51.2(2) . . . . ? C2 C1 C9 C10 127.51(14) . . . . ? O1 C1 C9 C8 -177.41(16) . . . . ? C2 C1 C9 C8 1.34(16) . . . . ? C7 C8 C9 C10 -124.97(13) . . . . ? C18 C8 C9 C10 114.35(13) . . . . ? C17 C8 C9 C10 -8.70(17) . . . . ? C7 C8 C9 C1 -1.68(14) . . . . ? C18 C8 C9 C1 -122.36(12) . . . . ? C17 C8 C9 C1 114.59(13) . . . . ? C1 C9 C10 C11 -72.83(16) . . . . ? C8 C9 C10 C11 48.06(17) . . . . ? C9 C10 C11 C12 -61.81(17) . . . . ? C10 C11 C12 C13 -141.66(15) . . . . ? C10 C11 C12 C17 36.32(19) . . . . ? C17 C12 C13 C14 1.8(2) . . . . ? C11 C12 C13 C14 179.82(16) . . . . ? C12 C13 C14 C15 -1.8(3) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C14 C15 C16 C17 1.0(3) . . . . ? C15 C16 C17 C12 -0.9(2) . . . . ? C15 C16 C17 C8 176.07(14) . . . . ? C13 C12 C17 C16 -0.4(2) . . . . ? C11 C12 C17 C16 -178.45(13) . . . . ? C13 C12 C17 C8 -177.38(13) . . . . ? C11 C12 C17 C8 4.6(2) . . . . ? C7 C8 C17 C16 -82.72(15) . . . . ? C18 C8 C17 C16 42.37(17) . . . . ? C9 C8 C17 C16 164.35(13) . . . . ? C7 C8 C17 C12 94.21(14) . . . . ? C18 C8 C17 C12 -140.70(13) . . . . ? C9 C8 C17 C12 -18.72(17) . . . . ? C7 C8 C18 C23 -7.28(19) . . . . ? C17 C8 C18 C23 -129.01(14) . . . . ? C9 C8 C18 C23 106.04(15) . . . . ? C7 C8 C18 C19 176.60(13) . . . . ? C17 C8 C18 C19 54.87(17) . . . . ? C9 C8 C18 C19 -70.07(17) . . . . ? C23 C18 C19 C20 0.0(3) . . . . ? C8 C18 C19 C20 176.38(17) . . . . ? C18 C19 C20 C21 0.1(3) . . . . ? C19 C20 C21 C22 0.1(3) . . . . ? C20 C21 C22 C23 -0.5(3) . . . . ? C19 C18 C23 C22 -0.4(2) . . . . ? C8 C18 C23 C22 -176.55(14) . . . . ? C21 C22 C23 C18 0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.182 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.028 data_cd211494 _database_code_depnum_ccdc_archive 'CCDC 855051' #TrackingRef 'cd211494.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 Br O' _chemical_formula_weight 389.28 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 7.6582(8) _cell_length_b 9.1199(10) _cell_length_c 14.2106(19) _cell_angle_alpha 71.294(2) _cell_angle_beta 81.511(3) _cell_angle_gamma 68.506(2) _cell_volume 874.18(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1977 _cell_measurement_theta_min 5.016 _cell_measurement_theta_max 54.399 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.321 _exptl_crystal_size_mid 0.225 _exptl_crystal_size_min 0.165 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 2.358 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0915 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 4813 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3377 _reflns_number_gt 2697 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0624P)^2^+0.2190P] 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 3377 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _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 0.74661(5) 0.76018(5) 0.52088(2) 0.07415(18) Uani 1 1 d . . . O1 O 0.0848(3) 0.6625(3) 0.28222(18) 0.0660(6) Uani 1 1 d . . . C1 C 0.2440(4) 0.6641(3) 0.2722(2) 0.0423(6) Uani 1 1 d . . . C2 C 0.3491(3) 0.6819(3) 0.34363(19) 0.0374(6) Uani 1 1 d . . . C3 C 0.2856(4) 0.7163(3) 0.4334(2) 0.0471(7) Uani 1 1 d . . . H3 H 0.1637 0.7243 0.4574 0.057 Uiso 1 1 calc R . . C4 C 0.4045(4) 0.7383(4) 0.4858(2) 0.0483(7) Uani 1 1 d . . . H4 H 0.3650 0.7615 0.5462 0.058 Uiso 1 1 calc R . . C5 C 0.5854(4) 0.7255(3) 0.44793(19) 0.0432(6) Uani 1 1 d . . . C6 C 0.6535(4) 0.6868(3) 0.36015(18) 0.0379(6) Uani 1 1 d . . . H6 H 0.7766 0.6759 0.3374 0.045 Uiso 1 1 calc R . . C7 C 0.5311(3) 0.6650(3) 0.30737(17) 0.0318(5) Uani 1 1 d . . . C8 C 0.5706(3) 0.6152(3) 0.21096(17) 0.0330(5) Uani 1 1 d . . . C9 C 0.3680(4) 0.6554(3) 0.17921(19) 0.0396(6) Uani 1 1 d . . . H9 H 0.3304 0.7663 0.1324 0.048 Uiso 1 1 calc R . . C10 C 0.3459(4) 0.5416(4) 0.1280(2) 0.0537(8) Uani 1 1 d . . . H10A H 0.2150 0.5736 0.1136 0.064 Uiso 1 1 calc R . . H10B H 0.4180 0.5506 0.0656 0.064 Uiso 1 1 calc R . . C11 C 0.4129(4) 0.3669(4) 0.1931(3) 0.0576(8) Uani 1 1 d . . . H11A H 0.4136 0.2943 0.1557 0.069 Uiso 1 1 calc R . . H11B H 0.3256 0.3542 0.2494 0.069 Uiso 1 1 calc R . . C12 C 0.6063(4) 0.3160(3) 0.2305(2) 0.0434(6) Uani 1 1 d . . . C13 C 0.6826(3) 0.4293(3) 0.23682(17) 0.0339(5) Uani 1 1 d . . . C14 C 0.8648(4) 0.3732(3) 0.26911(19) 0.0403(6) Uani 1 1 d . . . H14 H 0.9169 0.4491 0.2719 0.048 Uiso 1 1 calc R . . C15 C 0.9699(4) 0.2081(4) 0.2970(2) 0.0515(7) Uani 1 1 d . . . H15 H 1.0916 0.1730 0.3184 0.062 Uiso 1 1 calc R . . C16 C 0.8929(5) 0.0954(4) 0.2931(2) 0.0577(8) Uani 1 1 d . . . H16 H 0.9616 -0.0166 0.3127 0.069 Uiso 1 1 calc R . . C17 C 0.7151(5) 0.1491(4) 0.2602(2) 0.0566(8) Uani 1 1 d . . . H17 H 0.6648 0.0719 0.2576 0.068 Uiso 1 1 calc R . . C18 C 0.6725(3) 0.7128(3) 0.12898(17) 0.0338(5) Uani 1 1 d . . . C19 C 0.6560(4) 0.8709(3) 0.1244(2) 0.0470(7) Uani 1 1 d . . . H19 H 0.5855 0.9173 0.1733 0.056 Uiso 1 1 calc R . . C20 C 0.7428(5) 0.9610(4) 0.0481(2) 0.0573(8) Uani 1 1 d . . . H20 H 0.7324 1.0664 0.0470 0.069 Uiso 1 1 calc R . . C21 C 0.8443(4) 0.8964(4) -0.0261(2) 0.0552(8) Uani 1 1 d . . . H21 H 0.9047 0.9565 -0.0767 0.066 Uiso 1 1 calc R . . C22 C 0.8554(4) 0.7427(4) -0.0247(2) 0.0542(8) Uani 1 1 d . . . H22 H 0.9204 0.6994 -0.0758 0.065 Uiso 1 1 calc R . . C23 C 0.7709(4) 0.6508(3) 0.05210(19) 0.0443(6) Uani 1 1 d . . . H23 H 0.7803 0.5462 0.0522 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0767(3) 0.1288(4) 0.0509(2) -0.0463(2) 0.00749(16) -0.0597(3) O1 0.0337(11) 0.0994(17) 0.0809(16) -0.0450(14) 0.0076(10) -0.0281(11) C1 0.0297(14) 0.0459(15) 0.0529(16) -0.0181(12) 0.0007(11) -0.0122(12) C2 0.0333(13) 0.0401(14) 0.0405(13) -0.0145(11) 0.0049(10) -0.0143(11) C3 0.0373(15) 0.0576(17) 0.0479(16) -0.0231(13) 0.0120(12) -0.0163(13) C4 0.0531(17) 0.0607(17) 0.0358(14) -0.0231(13) 0.0135(12) -0.0227(14) C5 0.0494(16) 0.0536(16) 0.0350(13) -0.0164(12) 0.0000(11) -0.0247(13) C6 0.0355(13) 0.0515(15) 0.0334(12) -0.0172(11) 0.0039(10) -0.0202(12) C7 0.0328(12) 0.0311(12) 0.0312(12) -0.0088(10) 0.0021(9) -0.0120(10) C8 0.0334(13) 0.0395(13) 0.0303(12) -0.0127(10) 0.0008(9) -0.0160(11) C9 0.0340(13) 0.0462(15) 0.0393(14) -0.0100(11) -0.0060(10) -0.0147(11) C10 0.0436(16) 0.082(2) 0.0494(16) -0.0302(16) -0.0060(13) -0.0257(16) C11 0.0581(19) 0.070(2) 0.069(2) -0.0374(17) -0.0004(15) -0.0352(16) C12 0.0534(17) 0.0482(16) 0.0400(14) -0.0226(12) 0.0035(12) -0.0238(13) C13 0.0397(14) 0.0384(13) 0.0273(11) -0.0128(10) 0.0042(10) -0.0169(11) C14 0.0416(15) 0.0417(14) 0.0404(14) -0.0155(11) 0.0013(11) -0.0155(12) C15 0.0487(17) 0.0503(17) 0.0471(16) -0.0157(13) -0.0049(13) -0.0048(14) C16 0.073(2) 0.0387(16) 0.0543(18) -0.0163(13) -0.0009(16) -0.0090(15) C17 0.079(2) 0.0447(17) 0.0593(19) -0.0244(14) 0.0019(16) -0.0301(16) C18 0.0325(13) 0.0397(13) 0.0306(12) -0.0109(10) -0.0004(9) -0.0134(11) C19 0.0621(18) 0.0498(16) 0.0383(14) -0.0175(12) 0.0068(12) -0.0287(14) C20 0.076(2) 0.0548(18) 0.0501(17) -0.0077(14) 0.0005(15) -0.0399(17) C21 0.0485(17) 0.065(2) 0.0442(16) 0.0013(14) 0.0033(13) -0.0265(15) C22 0.0473(17) 0.064(2) 0.0365(15) -0.0114(13) 0.0100(12) -0.0090(14) C23 0.0476(16) 0.0435(15) 0.0376(14) -0.0125(12) 0.0043(12) -0.0123(13) _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 C5 1.890(3) . ? O1 C1 1.211(3) . ? C1 C2 1.466(4) . ? C1 C9 1.515(4) . ? C2 C7 1.383(3) . ? C2 C3 1.387(4) . ? C3 C4 1.361(4) . ? C3 H3 0.9300 . ? C4 C5 1.387(4) . ? C4 H4 0.9300 . ? C5 C6 1.381(4) . ? C6 C7 1.386(3) . ? C6 H6 0.9300 . ? C7 C8 1.533(3) . ? C8 C18 1.527(3) . ? C8 C13 1.541(3) . ? C8 C9 1.559(3) . ? C9 C10 1.511(4) . ? C9 H9 0.9800 . ? C10 C11 1.501(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.504(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.391(4) . ? C12 C17 1.397(4) . ? C13 C14 1.391(4) . ? C14 C15 1.377(4) . ? C14 H14 0.9300 . ? C15 C16 1.378(5) . ? C15 H15 0.9300 . ? C16 C17 1.365(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.382(4) . ? C18 C23 1.386(4) . ? C19 C20 1.382(4) . ? C19 H19 0.9300 . ? C20 C21 1.372(5) . ? C20 H20 0.9300 . ? C21 C22 1.367(5) . ? C21 H21 0.9300 . ? C22 C23 1.383(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 O1 C1 C2 127.4(3) . . ? O1 C1 C9 125.1(3) . . ? C2 C1 C9 107.5(2) . . ? C7 C2 C3 121.8(2) . . ? C7 C2 C1 109.6(2) . . ? C3 C2 C1 128.5(2) . . ? C4 C3 C2 118.9(2) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 123.1(3) . . ? C6 C5 Br1 118.6(2) . . ? C4 C5 Br1 118.3(2) . . ? C5 C6 C7 117.3(2) . . ? C5 C6 H6 121.3 . . ? C7 C6 H6 121.3 . . ? C2 C7 C6 119.7(2) . . ? C2 C7 C8 111.8(2) . . ? C6 C7 C8 128.4(2) . . ? C18 C8 C7 114.38(19) . . ? C18 C8 C13 110.91(19) . . ? C7 C8 C13 108.00(18) . . ? C18 C8 C9 109.90(19) . . ? C7 C8 C9 101.55(19) . . ? C13 C8 C9 111.8(2) . . ? C10 C9 C1 113.6(2) . . ? C10 C9 C8 115.6(2) . . ? C1 C9 C8 105.7(2) . . ? C10 C9 H9 107.2 . . ? C1 C9 H9 107.2 . . ? C8 C9 H9 107.2 . . ? C11 C10 C9 110.3(2) . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C10 C11 C12 112.7(2) . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C17 118.1(3) . . ? C13 C12 C11 122.5(2) . . ? C17 C12 C11 119.5(2) . . ? C14 C13 C12 119.2(2) . . ? C14 C13 C8 118.7(2) . . ? C12 C13 C8 122.2(2) . . ? C15 C14 C13 121.6(3) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C16 119.3(3) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C17 C16 C15 119.6(3) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C12 122.2(3) . . ? C16 C17 H17 118.9 . . ? C12 C17 H17 118.9 . . ? C19 C18 C23 117.9(2) . . ? C19 C18 C8 121.1(2) . . ? C23 C18 C8 120.9(2) . . ? C20 C19 C18 120.9(3) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C21 C20 C19 120.6(3) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 119.1(3) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C21 C22 C23 120.7(3) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C18 120.8(3) . . ? C22 C23 H23 119.6 . . ? C18 C23 H23 119.6 . . ? 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 O1 C1 C2 C7 175.5(3) . . . . ? C9 C1 C2 C7 -7.1(3) . . . . ? O1 C1 C2 C3 -6.8(5) . . . . ? C9 C1 C2 C3 170.7(3) . . . . ? C7 C2 C3 C4 1.8(4) . . . . ? C1 C2 C3 C4 -175.8(3) . . . . ? C2 C3 C4 C5 0.0(4) . . . . ? C3 C4 C5 C6 -1.8(5) . . . . ? C3 C4 C5 Br1 178.9(2) . . . . ? C4 C5 C6 C7 1.9(4) . . . . ? Br1 C5 C6 C7 -178.86(18) . . . . ? C3 C2 C7 C6 -1.7(4) . . . . ? C1 C2 C7 C6 176.3(2) . . . . ? C3 C2 C7 C8 175.9(2) . . . . ? C1 C2 C7 C8 -6.1(3) . . . . ? C5 C6 C7 C2 -0.1(4) . . . . ? C5 C6 C7 C8 -177.3(2) . . . . ? C2 C7 C8 C18 134.3(2) . . . . ? C6 C7 C8 C18 -48.3(3) . . . . ? C2 C7 C8 C13 -101.7(2) . . . . ? C6 C7 C8 C13 75.7(3) . . . . ? C2 C7 C8 C9 16.0(3) . . . . ? C6 C7 C8 C9 -166.6(2) . . . . ? O1 C1 C9 C10 -37.8(4) . . . . ? C2 C1 C9 C10 144.7(2) . . . . ? O1 C1 C9 C8 -165.6(3) . . . . ? C2 C1 C9 C8 16.9(3) . . . . ? C18 C8 C9 C10 92.7(3) . . . . ? C7 C8 C9 C10 -145.8(2) . . . . ? C13 C8 C9 C10 -30.9(3) . . . . ? C18 C8 C9 C1 -140.7(2) . . . . ? C7 C8 C9 C1 -19.2(2) . . . . ? C13 C8 C9 C1 95.7(2) . . . . ? C1 C9 C10 C11 -65.5(3) . . . . ? C8 C9 C10 C11 57.0(3) . . . . ? C9 C10 C11 C12 -51.1(3) . . . . ? C10 C11 C12 C13 22.9(4) . . . . ? C10 C11 C12 C17 -157.1(3) . . . . ? C17 C12 C13 C14 2.1(4) . . . . ? C11 C12 C13 C14 -177.9(2) . . . . ? C17 C12 C13 C8 -176.8(2) . . . . ? C11 C12 C13 C8 3.2(4) . . . . ? C18 C8 C13 C14 58.6(3) . . . . ? C7 C8 C13 C14 -67.4(3) . . . . ? C9 C8 C13 C14 -178.3(2) . . . . ? C18 C8 C13 C12 -122.5(2) . . . . ? C7 C8 C13 C12 111.5(2) . . . . ? C9 C8 C13 C12 0.6(3) . . . . ? C12 C13 C14 C15 -1.5(4) . . . . ? C8 C13 C14 C15 177.5(2) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C14 C15 C16 C17 1.0(5) . . . . ? C15 C16 C17 C12 -0.3(5) . . . . ? C13 C12 C17 C16 -1.3(4) . . . . ? C11 C12 C17 C16 178.7(3) . . . . ? C7 C8 C18 C19 -26.8(3) . . . . ? C13 C8 C18 C19 -149.2(2) . . . . ? C9 C8 C18 C19 86.6(3) . . . . ? C7 C8 C18 C23 158.8(2) . . . . ? C13 C8 C18 C23 36.4(3) . . . . ? C9 C8 C18 C23 -87.7(3) . . . . ? C23 C18 C19 C20 -3.1(4) . . . . ? C8 C18 C19 C20 -177.6(3) . . . . ? C18 C19 C20 C21 1.4(5) . . . . ? C19 C20 C21 C22 1.3(5) . . . . ? C20 C21 C22 C23 -2.1(5) . . . . ? C21 C22 C23 C18 0.3(5) . . . . ? C19 C18 C23 C22 2.3(4) . . . . ? C8 C18 C23 C22 176.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.649 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.058