data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 Br2' _chemical_formula_sum 'C18 H14 Br2' _chemical_formula_weight 390.11 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 8.1087(2) _cell_length_b 11.5770(3) _cell_length_c 32.9287(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3091.16(13) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 10003 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 5.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1563 _exptl_absorpt_correction_T_max 0.251 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9246 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2753 _reflns_number_gt 2172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0707P)^2^+1.0496P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2753 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 0.73244(7) -0.25239(4) -0.005973(17) 0.03429(19) Uani 1 1 d . . . Br2 Br 0.85765(7) -0.46282(4) 0.056948(17) 0.0395(2) Uani 1 1 d . . . C1 C 0.8255(6) -0.2206(4) 0.04551(15) 0.0266(11) Uani 1 1 d . . . C2 C 0.8739(5) -0.3050(4) 0.07075(15) 0.0265(10) Uani 1 1 d . . . C3 C 0.9463(6) -0.2815(4) 0.11148(15) 0.0296(11) Uani 1 1 d . . . H3A H 0.8832 -0.3217 0.1317 0.036 Uiso 1 1 d R . . H3B H 1.0584 -0.3081 0.1121 0.036 Uiso 1 1 d R . . C4 C 0.9472(5) -0.1565(4) 0.12370(14) 0.0245(10) Uani 1 1 d . . . C5 C 0.8955(5) -0.0723(4) 0.09836(14) 0.0246(10) Uani 1 1 d . . . C6 C 0.8409(6) -0.0960(4) 0.05587(14) 0.0307(11) Uani 1 1 d . . . H6A H 0.9210 -0.0611 0.0383 0.037 Uiso 1 1 d R . . H6B H 0.7363 -0.0585 0.0523 0.037 Uiso 1 1 d R . . C7 C 0.8892(5) 0.0521(4) 0.10995(15) 0.0246(10) Uani 1 1 d . . . C8 C 0.9704(5) 0.1353(4) 0.08681(15) 0.0256(10) Uani 1 1 d . . . H8 H 1.0287 0.1125 0.0627 0.031 Uiso 1 1 d R . . C9 C 0.9706(6) 0.2498(4) 0.09835(17) 0.0320(12) Uani 1 1 d . . . H9 H 1.0266 0.3057 0.0818 0.038 Uiso 1 1 d R . . C10 C 0.8899(6) 0.2831(4) 0.13276(16) 0.0332(12) Uani 1 1 d . . . H10 H 0.8910 0.3624 0.1412 0.040 Uiso 1 1 d R . . C11 C 0.8063(6) 0.2031(4) 0.15568(17) 0.0370(13) Uani 1 1 d . . . H11 H 0.7488 0.2273 0.1797 0.044 Uiso 1 1 d R . . C12 C 0.8063(6) 0.0881(4) 0.14436(16) 0.0319(11) Uani 1 1 d . . . H12 H 0.7469 0.0328 0.1604 0.038 Uiso 1 1 d R . . C13 C 1.0149(5) -0.1326(4) 0.16456(15) 0.0280(11) Uani 1 1 d . . . C14 C 1.1355(6) -0.0481(4) 0.17057(16) 0.0324(12) Uani 1 1 d . . . H14 H 1.1752 -0.0039 0.1479 0.039 Uiso 1 1 d R . . C15 C 1.1990(7) -0.0262(5) 0.20869(18) 0.0427(14) Uani 1 1 d . . . H15 H 1.2797 0.0336 0.2124 0.051 Uiso 1 1 d R . . C16 C 1.1453(8) -0.0890(6) 0.24168(18) 0.0512(16) Uani 1 1 d . . . H16 H 1.1920 -0.0755 0.2680 0.061 Uiso 1 1 d R . . C17 C 1.0282(8) -0.1724(6) 0.23638(18) 0.0522(16) Uani 1 1 d . . . H17 H 0.9880 -0.2152 0.2593 0.063 Uiso 1 1 d R . . C18 C 0.9635(7) -0.1961(5) 0.19820(16) 0.0376(12) Uani 1 1 d . . . H18 H 0.8829 -0.2562 0.1949 0.045 Uiso 1 1 d 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 0.0380(3) 0.0391(3) 0.0258(3) -0.0043(2) -0.0034(2) -0.0063(2) Br2 0.0496(3) 0.0242(3) 0.0449(4) -0.0051(2) 0.0000(3) -0.0050(2) C1 0.026(2) 0.029(3) 0.025(3) -0.004(2) 0.001(2) -0.007(2) C2 0.027(2) 0.025(2) 0.027(3) -0.002(2) 0.002(2) -0.0029(19) C3 0.033(3) 0.027(2) 0.029(3) 0.003(2) 0.005(2) -0.003(2) C4 0.026(2) 0.022(2) 0.025(3) -0.0013(19) 0.003(2) -0.0020(19) C5 0.026(2) 0.022(2) 0.026(3) -0.002(2) 0.005(2) -0.0021(18) C6 0.033(3) 0.028(3) 0.031(3) 0.001(2) 0.000(2) 0.000(2) C7 0.026(2) 0.026(2) 0.022(3) -0.0018(19) -0.0057(19) 0.0010(19) C8 0.027(2) 0.024(2) 0.026(3) 0.002(2) -0.003(2) 0.0035(19) C9 0.036(3) 0.026(3) 0.034(3) 0.003(2) -0.006(2) 0.002(2) C10 0.036(3) 0.026(2) 0.037(3) -0.005(2) -0.006(2) 0.006(2) C11 0.044(3) 0.037(3) 0.030(3) -0.007(2) 0.002(2) 0.012(2) C12 0.034(2) 0.033(3) 0.029(3) 0.000(2) 0.003(2) -0.002(2) C13 0.031(2) 0.027(2) 0.026(3) 0.003(2) 0.001(2) 0.003(2) C14 0.035(3) 0.031(3) 0.032(3) -0.002(2) -0.003(2) 0.002(2) C15 0.051(3) 0.037(3) 0.040(4) -0.007(3) -0.020(3) 0.002(2) C16 0.067(4) 0.057(4) 0.029(3) -0.006(3) -0.018(3) 0.010(3) C17 0.068(4) 0.056(4) 0.032(3) 0.009(3) 0.007(3) 0.009(3) C18 0.045(3) 0.041(3) 0.027(3) 0.005(2) -0.002(2) -0.001(2) _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 C1 1.892(5) . ? Br2 C2 1.887(5) . ? C1 C2 1.341(7) . ? C1 C6 1.487(7) . ? C2 C3 1.489(7) . ? C3 C4 1.502(6) . ? C3 H3A 0.9600 . ? C3 H3B 0.9599 . ? C4 C5 1.350(6) . ? C4 C13 1.479(7) . ? C5 C6 1.493(6) . ? C5 C7 1.491(6) . ? C6 H6A 0.9599 . ? C6 H6B 0.9600 . ? C7 C12 1.382(7) . ? C7 C8 1.394(6) . ? C8 C9 1.379(6) . ? C8 H8 0.9601 . ? C9 C10 1.364(7) . ? C9 H9 0.9600 . ? C10 C11 1.374(8) . ? C10 H10 0.9601 . ? C11 C12 1.382(7) . ? C11 H11 0.9601 . ? C12 H12 0.9599 . ? C13 C18 1.394(7) . ? C13 C14 1.397(6) . ? C14 C15 1.381(7) . ? C14 H14 0.9600 . ? C15 C16 1.378(9) . ? C15 H15 0.9600 . ? C16 C17 1.366(9) . ? C16 H16 0.9599 . ? C17 C18 1.390(8) . ? C17 H17 0.9600 . ? C18 H18 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 C2 C1 C6 122.7(5) . . ? C2 C1 Br1 122.0(4) . . ? C6 C1 Br1 115.3(4) . . ? C1 C2 C3 122.7(4) . . ? C1 C2 Br2 122.4(4) . . ? C3 C2 Br2 114.9(3) . . ? C2 C3 C4 114.8(4) . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3A 106.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 107.4 . . ? H3A C3 H3B 109.5 . . ? C5 C4 C13 122.9(4) . . ? C5 C4 C3 121.9(4) . . ? C13 C4 C3 115.2(4) . . ? C4 C5 C6 122.6(4) . . ? C4 C5 C7 123.4(4) . . ? C6 C5 C7 114.0(4) . . ? C1 C6 C5 114.7(4) . . ? C1 C6 H6A 109.1 . . ? C5 C6 H6A 106.7 . . ? C1 C6 H6B 109.7 . . ? C5 C6 H6B 107.0 . . ? H6A C6 H6B 109.5 . . ? C12 C7 C8 118.0(4) . . ? C12 C7 C5 121.2(4) . . ? C8 C7 C5 120.8(4) . . ? C9 C8 C7 121.0(5) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 120.0(5) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.2(5) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 119.3 . . ? C10 C11 C12 120.1(5) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 120.2 . . ? C7 C12 C11 120.8(5) . . ? C7 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C18 C13 C14 117.8(5) . . ? C18 C13 C4 120.9(4) . . ? C14 C13 C4 121.3(4) . . ? C15 C14 C13 121.3(5) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.1(5) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 119.5(5) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 121.2(6) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 118.8 . . ? C17 C18 C13 120.1(5) . . ? C17 C18 H18 120.2 . . ? C13 C18 H18 119.7 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.421 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.125