# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prof Keith Smith' _publ_contact_author_address ; Department of Chemistry University of Wales - Swansea Singleton Park Swansea SA2 8PP UNITED KINGDOM ; _publ_contact_author_email K.SMITH@SWANSEA.AC.UK _publ_section_title ; Bromination of cis,trans,trans-1,5,9-cyclododecatriene with bromine; an extensive study ; loop_ _publ_author_name 'Keith Smith' 'Alex D. Checquer' 'Simon G. Clement' 'Gamal A. El-Hiti' 'Oliver W. Howarth' ; M.B.Hursthouse ; 'Elfyn Jones' 'Gurvinder S. Kang' 'Chia-Hui Liu' data_03HUR307 _database_code_depnum_ccdc_archive 'CCDC 217888' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H18 Br6' _chemical_formula_weight 641.72 _chemical_melting_point ? _chemical_compound_source ? 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 Monoclinic _symmetry_space_group_name_H-M P21/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 15.676(4) _cell_length_b 6.4009(4) _cell_length_c 18.702(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.578(8) _cell_angle_gamma 90.00 _cell_volume 1732.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.460 _exptl_crystal_density_method ? _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 13.886 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7273 _diffrn_reflns_av_R_equivalents 0.0862 _diffrn_reflns_av_sigmaI/netI 0.1334 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2684 _reflns_number_observed 1967 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-92 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0448P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2684 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_obs 0.0451 _refine_ls_wR_factor_all 0.1116 _refine_ls_wR_factor_obs 0.1098 _refine_ls_goodness_of_fit_all 1.001 _refine_ls_goodness_of_fit_obs 1.163 _refine_ls_restrained_S_all 1.001 _refine_ls_restrained_S_obs 1.163 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.09005(7) 0.20233(13) 0.01009(5) 0.0224(3) Uani 1 d . . Br2 Br 0.03592(7) 0.32007(14) -0.17960(5) 0.0269(3) Uani 1 d . . Br3 Br 0.35120(7) 0.8056(2) -0.17455(6) 0.0310(3) Uani 1 d . . Br4 Br 0.36083(7) 1.23546(13) -0.05881(6) 0.0282(3) Uani 1 d . . Br5 Br 0.48245(7) 0.5817(2) 0.15929(6) 0.0291(3) Uani 1 d . . Br6 Br 0.34749(7) 0.6081(2) 0.27629(6) 0.0294(3) Uani 1 d . . C1 C 0.1415(6) 0.4504(13) -0.0227(5) 0.023(2) Uani 1 d . . H1 H 0.1955(6) 0.4045(13) -0.0326(5) 0.027 Uiso 1 calc R . C2 C 0.0710(6) 0.5387(13) -0.0987(5) 0.020(2) Uani 1 d . . H2 H 0.0154(6) 0.5775(13) -0.0897(5) 0.024 Uiso 1 calc R . C3 C 0.1047(7) 0.7318(13) -0.1275(6) 0.025(2) Uani 1 d . . H3A H 0.1194(7) 0.8393(13) -0.0880(6) 0.030 Uiso 1 calc R . H3B H 0.0549(7) 0.7839(13) -0.1732(6) 0.030 Uiso 1 calc R . C4 C 0.1920(6) 0.6930(13) -0.1478(5) 0.021(2) Uani 1 d . . H4A H 0.2295(6) 0.5842(13) -0.1142(5) 0.025 Uiso 1 calc R . H4B H 0.1718(6) 0.6432(13) -0.2007(5) 0.025 Uiso 1 calc R . C5 C 0.2510(6) 0.8862(13) -0.1391(5) 0.018(2) Uani 1 d . . H5 H 0.2130(6) 0.9938(13) -0.1742(5) 0.022 Uiso 1 calc R . C6 C 0.2919(6) 0.9772(12) -0.0591(5) 0.021(2) Uani 1 d . . H6 H 0.2394(6) 1.0201(12) -0.0463(5) 0.026 Uiso 1 calc R . C7 C 0.3534(6) 0.8382(13) 0.0093(5) 0.020(2) Uani 1 d . . H7A H 0.3232(6) 0.7046(13) 0.0068(5) 0.024 Uiso 1 calc R . H7B H 0.4118(6) 0.8125(13) 0.0042(5) 0.024 Uiso 1 calc R . C8 C 0.3715(6) 0.9371(13) 0.0861(5) 0.021(2) Uani 1 d . . H8A H 0.3180(6) 1.0214(13) 0.0810(5) 0.026 Uiso 1 calc R . H8B H 0.4233(6) 1.0319(13) 0.0972(5) 0.026 Uiso 1 calc R . C9 C 0.3920(6) 0.7962(13) 0.1561(5) 0.021(2) Uani 1 d . . H9 H 0.4228(6) 0.8852(13) 0.2013(5) 0.025 Uiso 1 calc R . C10 C 0.3087(6) 0.6994(13) 0.1683(5) 0.021(2) Uani 1 d . . H10 H 0.2647(6) 0.8137(13) 0.1617(5) 0.025 Uiso 1 calc R . C11 C 0.2550(7) 0.5268(13) 0.1125(6) 0.027(2) Uani 1 d . . H11A H 0.2968(7) 0.4532(13) 0.0942(6) 0.032 Uiso 1 calc R . H11B H 0.2328(7) 0.4275(13) 0.1405(6) 0.032 Uiso 1 calc R . C12 C 0.1748(6) 0.6051(14) 0.0442(5) 0.025(2) Uani 1 d . . H12A H 0.1922(6) 0.7343(14) 0.0263(5) 0.030 Uiso 1 calc R . H12B H 0.1242(6) 0.6360(14) 0.0603(5) 0.030 Uiso 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 0.0242(6) 0.0225(5) 0.0231(6) -0.0005(4) 0.0120(4) -0.0027(4) Br2 0.0328(6) 0.0246(6) 0.0196(5) -0.0043(4) 0.0059(4) -0.0037(4) Br3 0.0322(7) 0.0366(6) 0.0348(6) 0.0011(5) 0.0246(5) 0.0034(5) Br4 0.0247(6) 0.0205(5) 0.0421(7) 0.0072(4) 0.0159(5) -0.0005(4) Br5 0.0206(6) 0.0426(6) 0.0248(6) 0.0063(5) 0.0095(5) 0.0066(4) Br6 0.0259(6) 0.0447(6) 0.0181(5) 0.0007(4) 0.0091(4) -0.0036(5) C1 0.016(5) 0.025(5) 0.028(6) 0.001(4) 0.009(4) -0.006(4) C2 0.024(6) 0.021(5) 0.013(5) -0.004(4) 0.007(4) 0.001(4) C3 0.025(6) 0.022(5) 0.025(6) 0.001(4) 0.005(5) -0.005(4) C4 0.026(6) 0.021(5) 0.018(5) -0.004(4) 0.010(4) 0.001(4) C5 0.022(6) 0.020(5) 0.019(5) 0.012(4) 0.015(4) 0.009(4) C6 0.021(6) 0.016(5) 0.036(6) 0.008(4) 0.020(5) 0.004(4) C7 0.010(5) 0.027(5) 0.027(6) 0.005(4) 0.012(4) 0.005(4) C8 0.012(5) 0.024(5) 0.026(6) 0.001(4) 0.003(4) -0.005(4) C9 0.014(5) 0.023(5) 0.022(5) -0.005(4) 0.003(4) 0.003(4) C10 0.018(5) 0.024(5) 0.015(5) 0.011(4) 0.001(4) 0.002(4) C11 0.032(6) 0.014(5) 0.030(6) -0.004(4) 0.007(5) -0.006(4) C12 0.017(6) 0.030(6) 0.027(6) 0.005(4) 0.007(5) 0.001(4) _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 1.982(9) . ? Br2 C2 1.978(8) . ? Br3 C5 1.993(9) . ? Br4 C6 1.974(8) . ? Br5 C9 1.957(8) . ? Br6 C10 1.962(8) . ? C1 C12 1.522(12) . ? C1 C2 1.534(12) . ? C2 C3 1.522(12) . ? C3 C4 1.574(13) . ? C4 C5 1.515(12) . ? C5 C6 1.501(12) . ? C6 C7 1.552(12) . ? C7 C8 1.494(12) . ? C8 C9 1.519(12) . ? C9 C10 1.540(12) . ? C10 C11 1.530(12) . ? C11 C12 1.494(12) . ? 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 C12 C1 C2 114.8(7) . . ? C12 C1 Br1 108.6(6) . . ? C2 C1 Br1 110.3(6) . . ? C3 C2 C1 113.7(8) . . ? C3 C2 Br2 109.6(6) . . ? C1 C2 Br2 109.8(6) . . ? C2 C3 C4 114.2(7) . . ? C5 C4 C3 113.4(7) . . ? C6 C5 C4 115.6(7) . . ? C6 C5 Br3 110.0(6) . . ? C4 C5 Br3 106.2(5) . . ? C5 C6 C7 119.4(7) . . ? C5 C6 Br4 110.6(6) . . ? C7 C6 Br4 108.2(6) . . ? C8 C7 C6 112.2(7) . . ? C7 C8 C9 118.4(7) . . ? C8 C9 C10 117.1(7) . . ? C8 C9 Br5 110.8(6) . . ? C10 C9 Br5 111.0(6) . . ? C11 C10 C9 117.7(8) . . ? C11 C10 Br6 111.0(6) . . ? C9 C10 Br6 109.1(6) . . ? C12 C11 C10 113.8(7) . . ? C11 C12 C1 113.3(7) . . ? 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 C12 C1 C2 C3 56.2(11) . . . . ? Br1 C1 C2 C3 179.3(6) . . . . ? C12 C1 C2 Br2 179.4(6) . . . . ? Br1 C1 C2 Br2 -57.5(7) . . . . ? C1 C2 C3 C4 62.7(10) . . . . ? Br2 C2 C3 C4 -60.6(9) . . . . ? C2 C3 C4 C5 -152.6(8) . . . . ? C3 C4 C5 C6 61.5(10) . . . . ? C3 C4 C5 Br3 -176.2(6) . . . . ? C4 C5 C6 C7 56.6(11) . . . . ? Br3 C5 C6 C7 -63.7(9) . . . . ? C4 C5 C6 Br4 -176.9(6) . . . . ? Br3 C5 C6 Br4 62.7(6) . . . . ? C5 C6 C7 C8 -167.8(8) . . . . ? Br4 C6 C7 C8 64.7(8) . . . . ? C6 C7 C8 C9 153.6(8) . . . . ? C7 C8 C9 C10 -82.4(10) . . . . ? C7 C8 C9 Br5 46.2(10) . . . . ? C8 C9 C10 C11 71.5(10) . . . . ? Br5 C9 C10 C11 -57.0(9) . . . . ? C8 C9 C10 Br6 -160.8(6) . . . . ? Br5 C9 C10 Br6 70.6(6) . . . . ? C9 C10 C11 C12 -92.5(10) . . . . ? Br6 C10 C11 C12 140.8(7) . . . . ? C10 C11 C12 C1 161.2(8) . . . . ? C2 C1 C12 C11 -169.7(8) . . . . ? Br1 C1 C12 C11 66.3(9) . . . . ? _refine_diff_density_max 1.818 _refine_diff_density_min -1.017 _refine_diff_density_rms 0.269 data_03HUR315 _database_code_depnum_ccdc_archive 'CCDC 217896' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H18 Br4' _chemical_formula_weight 481.90 _chemical_melting_point ? _chemical_compound_source ? 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 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 6.5740(2) _cell_length_b 31.5300(6) _cell_length_c 7.6670(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.030(6) _cell_angle_gamma 90.00 _cell_volume 1511.16(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.118 _exptl_crystal_density_method ? _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 10.627 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2544 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 24.95 _reflns_number_total 1531 _reflns_number_observed 1419 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-92 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0568P)^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 ? _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 -0.04(3) _refine_ls_number_reflns 1531 _refine_ls_number_parameters 145 _refine_ls_number_restraints 74 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_obs 0.0396 _refine_ls_wR_factor_all 0.1050 _refine_ls_wR_factor_obs 0.1047 _refine_ls_goodness_of_fit_all 1.101 _refine_ls_goodness_of_fit_obs 1.144 _refine_ls_restrained_S_all 1.082 _refine_ls_restrained_S_obs 1.122 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.3074(2) 0.03975(4) 0.0709(2) 0.0228(3) Uani 1 d . . Br2 Br 0.8755(2) 0.02142(4) 0.2384(2) 0.0233(3) Uani 1 d . . Br3 Br 1.2856(2) 0.17388(4) 0.2344(2) 0.0275(4) Uani 1 d . . Br4 Br 0.8234(2) 0.23351(4) 0.2066(2) 0.0287(4) Uani 1 d . . C1 C 0.7198(19) 0.1085(4) -0.3251(17) 0.017(3) Uani 1 d U . H1 H 0.8505(19) 0.0946(4) -0.2833(17) 0.020 Uiso 1 calc R . C2 C 0.7249(20) 0.1509(4) -0.3332(18) 0.024(3) Uani 1 d U . H2 H 0.5935(20) 0.1644(4) -0.3799(18) 0.029 Uiso 1 calc R . C3 C 0.9172(21) 0.1790(4) -0.2757(20) 0.024(3) Uani 1 d U . H3A H 0.9288(21) 0.1943(4) -0.3819(20) 0.029 Uiso 1 calc R . H3B H 1.0444(21) 0.1616(4) -0.2293(20) 0.029 Uiso 1 calc R . C4 C 0.9067(21) 0.2110(4) -0.1267(19) 0.026(3) Uani 1 d U . H4A H 1.0444(21) 0.2249(4) -0.0797(19) 0.031 Uiso 1 calc R . H4B H 0.8014(21) 0.2326(4) -0.1825(19) 0.031 Uiso 1 calc R . C5 C 0.8492(19) 0.1911(4) 0.0337(17) 0.019(3) Uani 1 d U . H5 H 0.7048(19) 0.1796(4) -0.0198(17) 0.023 Uiso 1 calc R . C6 C 0.9869(18) 0.1535(4) 0.1217(18) 0.017(3) Uani 1 d U . H6 H 0.9874(18) 0.1335(4) 0.0237(18) 0.021 Uiso 1 calc R . C7 C 0.9194(19) 0.1290(4) 0.2658(17) 0.020(3) Uani 1 d U . H7A H 0.9024(19) 0.1485(4) 0.3582(17) 0.024 Uiso 1 calc R . H7B H 1.0297(19) 0.1087(4) 0.3258(17) 0.024 Uiso 1 calc R . C8 C 0.7094(19) 0.1058(4) 0.1781(17) 0.021(3) Uani 1 d U . H8A H 0.6090(19) 0.1255(4) 0.0993(17) 0.025 Uiso 1 calc R . H8B H 0.6511(19) 0.0972(4) 0.2745(17) 0.025 Uiso 1 calc R . C9 C 0.7240(19) 0.0662(4) 0.0641(18) 0.017(3) Uani 1 d U . H9 H 0.8156(19) 0.0737(4) -0.0106(18) 0.020 Uiso 1 calc R . C10 C 0.5139(19) 0.0497(4) -0.0666(18) 0.019(3) Uani 1 d U . H10 H 0.5431(19) 0.0223(4) -0.1144(18) 0.022 Uiso 1 calc R . C11 C 0.4072(22) 0.0776(4) -0.2279(19) 0.026(3) Uani 1 d U . H11A H 0.3934(22) 0.1059(4) -0.1824(19) 0.032 Uiso 1 calc R . H11B H 0.2638(22) 0.0669(4) -0.2858(19) 0.032 Uiso 1 calc R . C12 C 0.5216(19) 0.0815(4) -0.3776(18) 0.024(3) Uani 1 d U . H12A H 0.5597(19) 0.0533(4) -0.4072(18) 0.028 Uiso 1 calc R . H12B H 0.4212(19) 0.0932(4) -0.4879(18) 0.028 Uiso 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 0.0191(7) 0.0231(7) 0.0280(8) 0.0014(6) 0.0103(6) -0.0023(5) Br2 0.0225(7) 0.0201(7) 0.0276(8) 0.0076(6) 0.0080(6) 0.0011(5) Br3 0.0185(7) 0.0197(7) 0.0397(9) -0.0031(7) 0.0023(6) -0.0002(5) Br4 0.0318(9) 0.0216(7) 0.0353(9) -0.0073(6) 0.0140(7) 0.0050(5) C1 0.015(4) 0.020(5) 0.021(5) 0.002(4) 0.014(4) -0.001(4) C2 0.029(5) 0.024(5) 0.020(5) 0.002(4) 0.010(4) 0.003(4) C3 0.028(5) 0.019(5) 0.026(5) 0.006(4) 0.008(4) -0.010(4) C4 0.026(5) 0.026(5) 0.026(5) 0.003(4) 0.007(4) -0.004(4) C5 0.021(5) 0.020(5) 0.015(5) -0.001(4) 0.003(4) -0.005(4) C6 0.022(4) 0.012(4) 0.019(5) -0.004(4) 0.008(4) 0.001(4) C7 0.025(5) 0.015(4) 0.020(5) 0.002(4) 0.009(4) -0.001(4) C8 0.023(5) 0.024(5) 0.019(5) -0.004(4) 0.010(4) 0.006(4) C9 0.019(4) 0.011(4) 0.018(5) 0.003(4) 0.004(4) 0.002(3) C10 0.019(4) 0.017(4) 0.020(5) -0.001(4) 0.007(4) 0.002(3) C11 0.025(5) 0.031(5) 0.025(5) 0.003(4) 0.010(4) -0.005(4) C12 0.022(5) 0.026(5) 0.022(5) 0.001(4) 0.006(4) -0.000(4) _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 C10 1.985(12) . ? Br2 C9 1.988(12) . ? Br3 C6 1.992(12) . ? Br4 C5 1.927(13) . ? C1 C2 1.34(2) . ? C1 C12 1.50(2) . ? C1 H1 0.93 . ? C2 C3 1.49(2) . ? C2 H2 0.93 . ? C3 C4 1.54(2) . ? C3 H3A 0.97 . ? C3 H3B 0.97 . ? C4 C5 1.53(2) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C6 1.52(2) . ? C5 H5 0.98 . ? C6 C7 1.52(2) . ? C6 H6 0.98 . ? C7 C8 1.52(2) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.54(2) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 C10 1.53(2) . ? C9 H9 0.98 . ? C10 C11 1.50(2) . ? C10 H10 0.98 . ? C11 C12 1.56(2) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? 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 C12 125.8(12) . . ? C2 C1 H1 117.1(8) . . ? C12 C1 H1 117.1(7) . . ? C1 C2 C3 127.6(12) . . ? C1 C2 H2 116.2(8) . . ? C3 C2 H2 116.2(7) . . ? C2 C3 C4 112.3(10) . . ? C2 C3 H3A 109.1(7) . . ? C4 C3 H3A 109.1(7) . . ? C2 C3 H3B 109.1(7) . . ? C4 C3 H3B 109.1(7) . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 114.0(10) . . ? C5 C4 H4A 108.8(7) . . ? C3 C4 H4A 108.8(7) . . ? C5 C4 H4B 108.8(7) . . ? C3 C4 H4B 108.8(7) . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 114.6(10) . . ? C6 C5 Br4 113.8(9) . . ? C4 C5 Br4 111.4(9) . . ? C6 C5 H5 105.3(6) . . ? C4 C5 H5 105.3(7) . . ? Br4 C5 H5 105.3(4) . . ? C5 C6 C7 116.8(10) . . ? C5 C6 Br3 108.2(8) . . ? C7 C6 Br3 108.6(8) . . ? C5 C6 H6 107.7(7) . . ? C7 C6 H6 107.7(6) . . ? Br3 C6 H6 107.7(3) . . ? C6 C7 C8 110.6(10) . . ? C6 C7 H7A 109.5(6) . . ? C8 C7 H7A 109.5(6) . . ? C6 C7 H7B 109.5(6) . . ? C8 C7 H7B 109.5(6) . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 115.6(10) . . ? C7 C8 H8A 108.4(6) . . ? C9 C8 H8A 108.4(6) . . ? C7 C8 H8B 108.4(7) . . ? C9 C8 H8B 108.4(7) . . ? H8A C8 H8B 107.4 . . ? C10 C9 C8 116.5(10) . . ? C10 C9 Br2 111.2(8) . . ? C8 C9 Br2 107.4(8) . . ? C10 C9 H9 107.1(7) . . ? C8 C9 H9 107.1(7) . . ? Br2 C9 H9 107.1(4) . . ? C11 C10 C9 116.0(10) . . ? C11 C10 Br1 108.0(8) . . ? C9 C10 Br1 109.5(9) . . ? C11 C10 H10 107.7(7) . . ? C9 C10 H10 107.7(6) . . ? Br1 C10 H10 107.7(4) . . ? C10 C11 C12 116.3(11) . . ? C10 C11 H11A 108.2(7) . . ? C12 C11 H11A 108.2(7) . . ? C10 C11 H11B 108.2(7) . . ? C12 C11 H11B 108.2(7) . . ? H11A C11 H11B 107.4 . . ? C1 C12 C11 115.0(11) . . ? C1 C12 H12A 108.5(7) . . ? C11 C12 H12A 108.5(7) . . ? C1 C12 H12B 108.5(7) . . ? C11 C12 H12B 108.5(7) . . ? H12A C12 H12B 107.5 . . ? 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 C12 C1 C2 C3 177.5(12) . . . . ? C1 C2 C3 C4 -121.3(15) . . . . ? C2 C3 C4 C5 48.7(16) . . . . ? C3 C4 C5 C6 52.2(15) . . . . ? C3 C4 C5 Br4 -176.7(9) . . . . ? C4 C5 C6 C7 -172.5(11) . . . . ? Br4 C5 C6 C7 57.5(13) . . . . ? C4 C5 C6 Br3 64.7(12) . . . . ? Br4 C5 C6 Br3 -65.2(9) . . . . ? C5 C6 C7 C8 68.1(14) . . . . ? Br3 C6 C7 C8 -169.4(8) . . . . ? C6 C7 C8 C9 73.6(13) . . . . ? C7 C8 C9 C10 -163.6(11) . . . . ? C7 C8 C9 Br2 70.9(12) . . . . ? C8 C9 C10 C11 68.4(15) . . . . ? Br2 C9 C10 C11 -168.1(9) . . . . ? C8 C9 C10 Br1 -54.1(12) . . . . ? Br2 C9 C10 Br1 69.5(9) . . . . ? C9 C10 C11 C12 69.5(15) . . . . ? Br1 C10 C11 C12 -167.2(9) . . . . ? C2 C1 C12 C11 -81.4(17) . . . . ? C10 C11 C12 C1 -74.2(15) . . . . ? _refine_diff_density_max 0.836 _refine_diff_density_min -0.691 _refine_diff_density_rms 0.170 data_03HUR316 _database_code_depnum_ccdc_archive 'CCDC 217897' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H18 Br4' _chemical_formula_weight 481.90 _chemical_melting_point ? _chemical_compound_source ? 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 Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 9.9321(10) _cell_length_b 13.1468(5) _cell_length_c 11.9463(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.373(8) _cell_angle_gamma 90.00 _cell_volume 1471.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.175 _exptl_crystal_density_method ? _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 10.913 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6176 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0811 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.04 _reflns_number_total 2243 _reflns_number_observed 1732 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-92 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0940P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2243 _refine_ls_number_parameters 145 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_obs 0.0496 _refine_ls_wR_factor_all 0.1349 _refine_ls_wR_factor_obs 0.1320 _refine_ls_goodness_of_fit_all 0.950 _refine_ls_goodness_of_fit_obs 1.067 _refine_ls_restrained_S_all 0.964 _refine_ls_restrained_S_obs 1.079 _refine_ls_shift/esd_max -0.011 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.18801(8) 0.55627(6) 0.59897(8) 0.0200(3) Uani 1 d . . Br2 Br 0.29611(9) 0.56835(7) 0.91128(8) 0.0275(3) Uani 1 d . . Br3 Br 0.60162(9) 0.23817(6) 0.56648(8) 0.0235(3) Uani 1 d . . Br4 Br 0.84976(10) 0.27165(7) 0.88320(8) 0.0312(3) Uani 1 d . . C1 C 0.6402(12) 0.6644(8) 0.8134(12) 0.056(3) Uani 1 d U . H1A H 0.6725(12) 0.7317(8) 0.8441(12) 0.067 Uiso 1 calc R . H1B H 0.6868(12) 0.6170(8) 0.8766(12) 0.067 Uiso 1 calc R . C2 C 0.4790(9) 0.6604(6) 0.7990(8) 0.025(2) Uani 1 d U . H2A H 0.4609(9) 0.7072(6) 0.8552(8) 0.030 Uiso 1 calc R . H2B H 0.4242(9) 0.6836(6) 0.7198(8) 0.030 Uiso 1 calc R . C3 C 0.4267(9) 0.5550(6) 0.8181(8) 0.021(2) Uani 1 d U . H3 H 0.5105(9) 0.5177(6) 0.8682(8) 0.025 Uiso 1 calc R . C4 C 0.3569(9) 0.4883(6) 0.7119(8) 0.018(2) Uani 1 d U . H4 H 0.3236(9) 0.4265(6) 0.7404(8) 0.022 Uiso 1 calc R . C5 C 0.4534(9) 0.4558(6) 0.6416(8) 0.019(2) Uani 1 d U . H5A H 0.4813(9) 0.5151(6) 0.6064(8) 0.022 Uiso 1 calc R . H5B H 0.4014(9) 0.4103(6) 0.5780(8) 0.022 Uiso 1 calc R . C6 C 0.5882(8) 0.4013(6) 0.7233(7) 0.017(2) Uani 1 d U . H6A H 0.6410(8) 0.4482(6) 0.7850(7) 0.021 Uiso 1 calc R . H6B H 0.5589(8) 0.3444(6) 0.7615(7) 0.021 Uiso 1 calc R . C7 C 0.6862(8) 0.3626(5) 0.6587(7) 0.016(2) Uani 1 d U . H7 H 0.6884(8) 0.4149(5) 0.6009(7) 0.019 Uiso 1 calc R . C8 C 0.8404(9) 0.3407(6) 0.7330(8) 0.020(2) Uani 1 d U . H8 H 0.8756(9) 0.2914(6) 0.6878(8) 0.024 Uiso 1 calc R . C9 C 0.9423(10) 0.4298(6) 0.7567(10) 0.033(2) Uani 1 d U . H9A H 0.9526(10) 0.4506(6) 0.6820(10) 0.039 Uiso 1 calc R . H9B H 1.0351(10) 0.4069(6) 0.8079(10) 0.039 Uiso 1 calc R . C10 C 0.8961(15) 0.5305(10) 0.8184(15) 0.081(4) Uani 1 d U . H10 H 0.9204(15) 0.5471(10) 0.8983(15) 0.097 Uiso 1 calc R . C11 C 0.8190(16) 0.5793(11) 0.7283(14) 0.082(4) Uani 1 d U . H11 H 0.8375(16) 0.5740(11) 0.6572(14) 0.098 Uiso 1 calc R . C12 C 0.6922(16) 0.6486(10) 0.7348(13) 0.078(4) Uani 1 d U . H12A H 0.7168(16) 0.7158(10) 0.7143(13) 0.094 Uiso 1 calc R . H12B H 0.6116(16) 0.6269(10) 0.6675(13) 0.094 Uiso 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 0.0133(4) 0.0277(5) 0.0180(5) 0.0044(4) 0.0039(4) 0.0042(4) Br2 0.0284(5) 0.0380(5) 0.0184(6) 0.0017(4) 0.0109(4) 0.0107(4) Br3 0.0244(5) 0.0250(5) 0.0232(6) -0.0081(4) 0.0106(4) -0.0043(4) Br4 0.0316(6) 0.0437(6) 0.0178(6) 0.0043(4) 0.0074(5) 0.0161(5) C1 0.050(5) 0.046(5) 0.079(6) -0.014(4) 0.032(5) -0.003(4) C2 0.025(4) 0.022(4) 0.030(4) -0.008(3) 0.010(4) -0.001(3) C3 0.018(4) 0.026(4) 0.020(4) 0.000(3) 0.009(3) 0.008(3) C4 0.020(4) 0.016(3) 0.019(4) 0.004(3) 0.007(3) 0.006(3) C5 0.014(3) 0.020(4) 0.024(4) 0.001(3) 0.009(3) -0.004(3) C6 0.015(3) 0.016(3) 0.022(4) 0.000(3) 0.006(3) -0.001(3) C7 0.019(4) 0.011(3) 0.018(4) -0.001(3) 0.007(3) -0.004(3) C8 0.023(4) 0.021(4) 0.019(4) -0.004(3) 0.011(3) 0.001(3) C9 0.023(4) 0.031(4) 0.047(5) -0.011(4) 0.015(4) -0.004(4) C10 0.069(6) 0.073(6) 0.090(7) 0.007(5) 0.010(5) -0.016(5) C11 0.086(6) 0.087(6) 0.075(6) 0.005(5) 0.031(5) -0.032(5) C12 0.086(6) 0.067(6) 0.078(7) 0.004(5) 0.022(5) -0.013(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 C4 1.982(8) . ? Br2 C3 1.978(8) . ? Br3 C7 1.995(8) . ? Br4 C8 1.985(8) . ? C1 C12 1.23(2) . ? C1 C2 1.553(13) . ? C2 C3 1.524(11) . ? C3 C4 1.508(12) . ? C4 C5 1.530(11) . ? C5 C6 1.546(12) . ? C6 C7 1.518(10) . ? C7 C8 1.522(12) . ? C8 C9 1.512(12) . ? C9 C10 1.65(2) . ? C10 C11 1.27(2) . ? C11 C12 1.58(2) . ? 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 C12 C1 C2 126.0(13) . . ? C3 C2 C1 113.8(7) . . ? C4 C3 C2 119.2(7) . . ? C4 C3 Br2 108.7(5) . . ? C2 C3 Br2 108.8(5) . . ? C3 C4 C5 115.3(7) . . ? C3 C4 Br1 111.1(5) . . ? C5 C4 Br1 107.2(6) . . ? C4 C5 C6 110.6(7) . . ? C7 C6 C5 113.7(7) . . ? C6 C7 C8 117.2(7) . . ? C6 C7 Br3 109.4(5) . . ? C8 C7 Br3 109.0(5) . . ? C9 C8 C7 116.4(7) . . ? C9 C8 Br4 111.0(6) . . ? C7 C8 Br4 110.5(5) . . ? C8 C9 C10 115.9(8) . . ? C11 C10 C9 101.9(15) . . ? C10 C11 C12 121.2(15) . . ? C1 C12 C11 132.8(14) . . ? 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 C12 C1 C2 C3 87.9(16) . . . . ? C1 C2 C3 C4 -96.2(10) . . . . ? C1 C2 C3 Br2 138.5(7) . . . . ? C2 C3 C4 C5 64.3(10) . . . . ? Br2 C3 C4 C5 -170.3(5) . . . . ? C2 C3 C4 Br1 -57.8(8) . . . . ? Br2 C3 C4 Br1 67.6(6) . . . . ? C3 C4 C5 C6 56.1(9) . . . . ? Br1 C4 C5 C6 -179.7(5) . . . . ? C4 C5 C6 C7 177.4(6) . . . . ? C5 C6 C7 C8 160.0(7) . . . . ? C5 C6 C7 Br3 -75.2(7) . . . . ? C6 C7 C8 C9 -85.9(9) . . . . ? Br3 C7 C8 C9 149.1(6) . . . . ? C6 C7 C8 Br4 41.8(8) . . . . ? Br3 C7 C8 Br4 -83.2(5) . . . . ? C7 C8 C9 C10 55.2(12) . . . . ? Br4 C8 C9 C10 -72.2(10) . . . . ? C8 C9 C10 C11 -87.7(13) . . . . ? C9 C10 C11 C12 149.7(12) . . . . ? C2 C1 C12 C11 -130.6(16) . . . . ? C10 C11 C12 C1 -4.7(26) . . . . ? _refine_diff_density_max 2.762 _refine_diff_density_min -1.153 _refine_diff_density_rms 0.212 data_03HUR317 _database_code_depnum_ccdc_archive 'CCDC 217898' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H18 Br4' _chemical_formula_weight 481.90 _chemical_melting_point ? _chemical_compound_source ? 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 Monoclinic _symmetry_space_group_name_H-M P21/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 11.4559(14) _cell_length_b 7.4771(13) _cell_length_c 17.7504(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.342(7) _cell_angle_gamma 90.00 _cell_volume 1520.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.106 _exptl_crystal_density_method ? _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 10.565 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5014 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0915 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 24.95 _reflns_number_total 2240 _reflns_number_observed 1670 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-92 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0530P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2240 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_obs 0.0442 _refine_ls_wR_factor_all 0.1089 _refine_ls_wR_factor_obs 0.1075 _refine_ls_goodness_of_fit_all 0.967 _refine_ls_goodness_of_fit_obs 1.117 _refine_ls_restrained_S_all 0.967 _refine_ls_restrained_S_obs 1.117 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.87985(6) 0.17068(10) 0.70152(4) 0.0274(2) Uani 1 d . . Br2 Br 0.56391(6) 0.22878(9) 0.69655(4) 0.0268(2) Uani 1 d . . Br3 Br 0.50886(6) 0.25544(10) 0.41339(5) 0.0311(3) Uani 1 d . . Br4 Br 0.76711(7) 0.24833(10) 0.30366(4) 0.0360(3) Uani 1 d . . C1 C 0.7152(5) 0.4420(9) 0.3713(4) 0.019(2) Uani 1 d . . H1 H 0.6559(5) 0.5133(9) 0.3443(4) 0.023 Uiso 1 calc R . C2 C 0.6608(5) 0.3631(8) 0.4411(4) 0.0171(15) Uani 1 d . . H2 H 0.6450(5) 0.4631(8) 0.4750(4) 0.021 Uiso 1 calc R . C3 C 0.7339(6) 0.2300(8) 0.4856(4) 0.018(2) Uani 1 d . . H3A H 0.8106(6) 0.2815(8) 0.4948(4) 0.022 Uiso 1 calc R . H3B H 0.7440(6) 0.1241(8) 0.4548(4) 0.022 Uiso 1 calc R . C4 C 0.6841(6) 0.1723(9) 0.5616(4) 0.024(2) Uani 1 d . . H4A H 0.6062(6) 0.1252(9) 0.5522(4) 0.028 Uiso 1 calc R . H4B H 0.7318(6) 0.0749(9) 0.5813(4) 0.028 Uiso 1 calc R . C5 C 0.6768(5) 0.3136(9) 0.6219(4) 0.019(2) Uani 1 d . . H5 H 0.6418(5) 0.4193(9) 0.5978(4) 0.023 Uiso 1 calc R . C6 C 0.7851(5) 0.3755(8) 0.6619(4) 0.019(2) Uani 1 d . . H6 H 0.7600(5) 0.4434(8) 0.7059(4) 0.023 Uiso 1 calc R . C7 C 0.8689(5) 0.4976(9) 0.6192(4) 0.021(2) Uani 1 d . . H7A H 0.9371(5) 0.5209(9) 0.6511(4) 0.025 Uiso 1 calc R . H7B H 0.8948(5) 0.4352(9) 0.5747(4) 0.025 Uiso 1 calc R . C8 C 0.8150(5) 0.6757(8) 0.5951(4) 0.0152(15) Uani 1 d . . H8A H 0.7435(5) 0.6536(8) 0.5663(4) 0.018 Uiso 1 calc R . H8B H 0.7954(5) 0.7438(8) 0.6396(4) 0.018 Uiso 1 calc R . C9 C 0.8964(6) 0.7824(8) 0.5485(4) 0.023(2) Uani 1 d . . H9 H 0.9609(6) 0.8331(8) 0.5731(4) 0.027 Uiso 1 calc R . C10 C 0.8847(6) 0.8112(9) 0.4751(4) 0.024(2) Uani 1 d . . H10 H 0.9413(6) 0.8813(9) 0.4527(4) 0.029 Uiso 1 calc R . C11 C 0.7882(6) 0.7408(9) 0.4248(4) 0.022(2) Uani 1 d . . H11A H 0.7710(6) 0.8273(9) 0.3853(4) 0.027 Uiso 1 calc R . H11B H 0.7183(6) 0.7258(9) 0.4540(4) 0.027 Uiso 1 calc R . C12 C 0.8200(5) 0.5613(9) 0.3888(4) 0.020(2) Uani 1 d . . H12A H 0.8606(5) 0.5843(9) 0.3424(4) 0.024 Uiso 1 calc R . H12B H 0.8734(5) 0.4979(9) 0.4226(4) 0.024 Uiso 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 0.0249(5) 0.0262(4) 0.0311(5) 0.0100(4) -0.0003(3) 0.0029(3) Br2 0.0230(5) 0.0312(5) 0.0264(5) 0.0054(3) 0.0071(3) -0.0068(3) Br3 0.0207(5) 0.0290(5) 0.0433(5) 0.0037(4) -0.0067(3) -0.0066(3) Br4 0.0543(6) 0.0309(5) 0.0231(5) -0.0098(4) 0.0090(4) 0.0004(4) C1 0.021(4) 0.016(4) 0.021(4) 0.002(3) 0.005(3) 0.004(3) C2 0.016(4) 0.012(4) 0.023(4) -0.003(3) -0.002(3) -0.001(3) C3 0.016(4) 0.017(4) 0.022(4) -0.001(3) 0.002(3) 0.004(3) C4 0.032(4) 0.014(4) 0.025(4) 0.002(3) 0.003(3) -0.005(3) C5 0.022(4) 0.016(4) 0.020(4) 0.011(3) 0.008(3) -0.003(3) C6 0.016(4) 0.014(4) 0.026(4) 0.007(3) -0.000(3) 0.007(3) C7 0.014(4) 0.016(4) 0.033(5) -0.000(3) 0.005(3) -0.000(3) C8 0.014(4) 0.016(4) 0.016(4) 0.001(3) 0.000(3) -0.001(3) C9 0.021(4) 0.013(4) 0.034(5) -0.005(3) 0.004(3) -0.003(3) C10 0.022(4) 0.015(4) 0.037(5) -0.003(3) 0.009(3) -0.007(3) C11 0.029(4) 0.017(4) 0.021(4) 0.008(3) -0.002(3) 0.003(3) C12 0.018(4) 0.018(4) 0.025(4) 0.004(3) 0.003(3) 0.000(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 C6 1.996(6) . ? Br2 C5 1.977(6) . ? Br3 C2 1.969(6) . ? Br4 C1 1.981(6) . ? C1 C2 1.519(9) . ? C1 C12 1.522(9) . ? C2 C3 1.511(9) . ? C3 C4 1.538(9) . ? C4 C5 1.509(10) . ? C5 C6 1.489(9) . ? C6 C7 1.537(8) . ? C7 C8 1.524(9) . ? C8 C9 1.492(9) . ? C9 C10 1.324(10) . ? C10 C11 1.500(10) . ? C11 C12 1.534(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 C2 C1 C12 113.5(6) . . ? C2 C1 Br4 110.2(4) . . ? C12 C1 Br4 107.8(4) . . ? C3 C2 C1 116.7(5) . . ? C3 C2 Br3 109.7(4) . . ? C1 C2 Br3 109.4(4) . . ? C2 C3 C4 115.5(5) . . ? C5 C4 C3 117.0(6) . . ? C6 C5 C4 119.8(5) . . ? C6 C5 Br2 109.4(4) . . ? C4 C5 Br2 107.4(4) . . ? C5 C6 C7 118.2(6) . . ? C5 C6 Br1 111.7(4) . . ? C7 C6 Br1 106.8(4) . . ? C8 C7 C6 113.8(5) . . ? C9 C8 C7 111.6(5) . . ? C10 C9 C8 125.6(7) . . ? C9 C10 C11 125.8(6) . . ? C10 C11 C12 112.1(5) . . ? C1 C12 C11 113.8(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 C12 C1 C2 C3 -66.7(7) . . . . ? Br4 C1 C2 C3 54.3(7) . . . . ? C12 C1 C2 Br3 168.1(4) . . . . ? Br4 C1 C2 Br3 -71.0(4) . . . . ? C1 C2 C3 C4 171.8(6) . . . . ? Br3 C2 C3 C4 -63.1(7) . . . . ? C2 C3 C4 C5 -66.1(8) . . . . ? C3 C4 C5 C6 -73.7(8) . . . . ? C3 C4 C5 Br2 160.9(5) . . . . ? C4 C5 C6 C7 73.7(8) . . . . ? Br2 C5 C6 C7 -161.8(4) . . . . ? C4 C5 C6 Br1 -50.8(7) . . . . ? Br2 C5 C6 Br1 73.7(5) . . . . ? C5 C6 C7 C8 61.9(8) . . . . ? Br1 C6 C7 C8 -171.2(5) . . . . ? C6 C7 C8 C9 -175.2(6) . . . . ? C7 C8 C9 C10 108.0(8) . . . . ? C8 C9 C10 C11 -0.6(11) . . . . ? C9 C10 C11 C12 -92.2(8) . . . . ? C2 C1 C12 C11 -71.5(7) . . . . ? Br4 C1 C12 C11 166.2(5) . . . . ? C10 C11 C12 C1 151.1(6) . . . . ? _refine_diff_density_max 1.062 _refine_diff_density_min -0.910 _refine_diff_density_rms 0.218 data_compound_03HUR967 _database_code_depnum_ccdc_archive 'CCDC 260841' _audit_creation_method 'manually at CCDC' _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_sum C12H18Br2 _chemical_formula_moiety ? _chemical_formula_weight 322.08 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a _symmetry_Int_Tables_number ? loop_ _symmetry_equiv_pos_as_xyz ? ? ? _cell_length_a 7.733 _cell_length_b 15.842 _cell_length_c 10.62 _cell_angle_alpha 90 _cell_angle_beta 102.83 _cell_angle_gamma 90 _cell_volume 1268.53 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.68 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_special_details ; ? ; _exptl_absorpt_correction_type ? _exptl_absorpt_coefficient_mu 62.94 _exptl_crystal_F_000 640 _diffrn_ambient_temperature 293 _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo k alpha' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_number 9725 _diffrn_reflns_theta_max 23 _diffrn_reflns_av_R_equivalents ? _reflns_number_total 9725 _reflns_observed_criterion Fo>3sigma(Fo) _reflns_number_gt 2475 _refine_ls_R_factor_gt 0.079 _refine_ls_wR_factor_ref 0.076 _refine_ls_number_reflns 2475 _refine_ls_hydrogen_treatment ? _refine_ls_number_parameters 145 _refine_ls_number_restraints ? _refine_special_details ; ? ; _refine_diff_density_max ? _refine_diff_density_min ? loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z Br1 0.0210,2 0.6514,1 0.8705,1 Br2 0.0292,2 0.6344,1 0.5328,1 C1 0.0857,11 0.5521,5 0.7773,8 C2 0.1905,12 0.5801,5 0.6802,8 C3 0.3486,11 0.6357,5 0.7273,8 C4 0.4922,12 0.6270,7 0.6499,10 C5 0.5817,12 0.5417,7 0.6595,10 C6 0.5979,12 0.4860,7 0.7483,10 C7 0.6818,13 0.4012,7 0.7518,10 C8 0.5484,13 0.3284,6 0.7530,10 C9 0.4905,13 0.3224,5 0.8776,9 C10 0.3486,11 0.3532,6 0.9064,9 C11 0.2099,11 0.4040,5 0.8196,9 C12 0.1896,12 0.4911,5 0.8795,8 H11 -0.0390,77 0.5278,37 0.7165,56 H21 0.2166,81 0.5392,40 0.6502,59 H31 0.3071,11 0.6930,5 0.7206,8 H32 0.3995,11 0.6227,5 0.8161,8 H41 0.4394,12 0.6379,7 0.5607,10 H42 0.5823,12 0.6683,7 0.6809,10 H51 0.6308,12 0.5256,7 0.5876,10 H61 0.5513,12 0.5015,7 0.8217,10 H71 0.7316,13 0.3958,7 0.6771,10 H72 0.7748,13 0.3979,7 0.8284,10 H81 0.6075,13 0.2768,6 0.7405,10 H82 0.4462,13 0.3357,6 0.6838,10 H91 0.5679,13 0.2919,5 0.9456,9 H101 0.3305,11 0.3409,6 0.9911,9 H111 0.2431,11 0.4121,5 0.7385,9 H112 0.0982,11 0.3750,5 0.8053,9 H121 0.1277,12 0.4845,5 0.9479,8 H122 0.3050,12 0.5144,5 0.9137,8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 Br1 1.981,9 C2 Br2 1.970,10 C2 C1 1.512,14 C12 C1 1.540,13 C3 C2 1.501,13 C4 C3 1.527,14 C5 C4 1.512,16 C6 C5 1.277,14 C7 C6 1.488,14 C8 C7 1.550,15 C9 C8 1.491,14 C10 C9 1.298,13 C11 C10 1.486,12 C12 C11 1.542,14 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 ? ? ? ? ? ? ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle ? ? ? ? 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 ? ? ? ? ? data_05sjc00001 _database_code_depnum_ccdc_archive 'CCDC 261191' _audit_creation_date 2005-01-18T23:04:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C14 H21 Br6 N' _chemical_formula_weight 682.78 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 10.2529(7) _cell_length_b 13.9866(17) _cell_length_c 14.4984(13) _cell_angle_alpha 75.851(7) _cell_angle_beta 79.144(7) _cell_angle_gamma 83.639(8) _cell_volume 1975.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8853 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 2.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 12.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number none _diffrn_standards_decay_% negligible _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_unetI/netI 0.0661 _diffrn_reflns_number 39119 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 9016 _reflns_number_gt 7371 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0598P)^2^+7.3754P] 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_number_reflns 9016 _refine_ls_number_parameters 381 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.166 _refine_diff_density_min -1.923 _refine_diff_density_rms 0.255 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' 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 C1 C 0.6416(5) -0.0167(4) 0.2221(4) 0.0118(11) Uani 1 1 d . . . H1 H 0.5985 -0.0595 0.2837 0.014 Uiso 1 1 calc R . . C2 C 0.6374(5) 0.0870(4) 0.2389(4) 0.0109(11) Uani 1 1 d . . . H2 H 0.6967 0.086 0.2865 0.013 Uiso 1 1 calc R . . C3 C 0.4984(6) 0.1280(4) 0.2764(4) 0.0119(11) Uani 1 1 d . . . H3A H 0.4373 0.1236 0.2325 0.014 Uiso 1 1 calc R . . H3B H 0.5019 0.1987 0.2753 0.014 Uiso 1 1 calc R . . C4 C 0.4420(5) 0.0730(4) 0.3797(4) 0.0119(11) Uani 1 1 d . . . H4A H 0.4583 0.0008 0.3856 0.014 Uiso 1 1 calc R . . H4B H 0.4882 0.0914 0.4263 0.014 Uiso 1 1 calc R . . C5 C 0.2925(5) 0.0990(4) 0.4035(4) 0.0107(11) Uani 1 1 d U . . H5 H 0.2763 0.1724 0.3844 0.013 Uiso 1 1 calc R . . C6 C 0.2128(5) 0.0531(4) 0.3499(4) 0.0093(10) Uani 1 1 d . . . H6 H 0.2567 0.0668 0.2807 0.011 Uiso 1 1 calc R . . C7 C 0.2021(6) -0.0579(4) 0.3834(4) 0.0118(11) Uani 1 1 d . . . H7A H 0.133 -0.0715 0.4418 0.014 Uiso 1 1 calc R . . H7B H 0.2879 -0.0889 0.4019 0.014 Uiso 1 1 calc R . . C8 C 0.1678(6) -0.1067(4) 0.3083(4) 0.0125(11) Uani 1 1 d . . . H8A H 0.0833 -0.075 0.2879 0.015 Uiso 1 1 calc R . . H8B H 0.1546 -0.1774 0.3376 0.015 Uiso 1 1 calc R . . C9 C 0.2785(5) -0.0975(4) 0.2196(4) 0.0100(11) Uani 1 1 d . . . H9 H 0.3 -0.0266 0.2005 0.012 Uiso 1 1 calc R . . C10 C 0.4083(6) -0.1576(4) 0.2361(4) 0.0122(11) Uani 1 1 d . . . H10 H 0.4324 -0.1444 0.2953 0.015 Uiso 1 1 calc R . . C11 C 0.5267(6) -0.1330(4) 0.1553(4) 0.0159(12) Uani 1 1 d . . . H11A H 0.503 -0.1394 0.0941 0.019 Uiso 1 1 calc R . . H11B H 0.6026 -0.1813 0.1696 0.019 Uiso 1 1 calc R . . C12 C 0.5700(5) -0.0278(4) 0.1425(4) 0.0112(11) Uani 1 1 d . . . H12A H 0.6297 -0.0096 0.0797 0.013 Uiso 1 1 calc R . . H12B H 0.4903 0.019 0.1407 0.013 Uiso 1 1 calc R . . C13 C 0.7615(5) 0.6362(4) 0.3862(4) 0.0111(11) Uani 1 1 d . . . H13 H 0.7571 0.638 0.3174 0.013 Uiso 1 1 calc R . . C14 C 0.8936(6) 0.6751(4) 0.3878(4) 0.0130(11) Uani 1 1 d . . . H14 H 0.8935 0.7456 0.3511 0.016 Uiso 1 1 calc R . . C15 C 1.0147(6) 0.6189(4) 0.3421(4) 0.0156(12) Uani 1 1 d . . . H15A H 1.0109 0.5476 0.3728 0.019 Uiso 1 1 calc R . . H15B H 1.0963 0.6414 0.3551 0.019 Uiso 1 1 calc R . . C16 C 1.0242(6) 0.6332(4) 0.2327(4) 0.0152(12) Uani 1 1 d . . . H16A H 1.0523 0.7003 0.2 0.018 Uiso 1 1 calc R . . H16B H 0.9353 0.6276 0.218 0.018 Uiso 1 1 calc R . . C17 C 1.1241(6) 0.5559(4) 0.1935(4) 0.0129(11) Uani 1 1 d . . . H17 H 1.2058 0.5503 0.2234 0.016 Uiso 1 1 calc R . . C18 C 1.0694(5) 0.4544(4) 0.2187(4) 0.0120(11) Uani 1 1 d . . . H18 H 1.0328 0.4399 0.2893 0.014 Uiso 1 1 calc R . . C19 C 0.9573(6) 0.4430(4) 0.1673(4) 0.0138(12) Uani 1 1 d . . . H19A H 0.9965 0.4323 0.1025 0.017 Uiso 1 1 calc R . . H19B H 0.9002 0.5053 0.1584 0.017 Uiso 1 1 calc R . . C20 C 0.8704(6) 0.3576(4) 0.2211(4) 0.0110(11) Uani 1 1 d . . . H20A H 0.8068 0.3505 0.1799 0.013 Uiso 1 1 calc R . . H20B H 0.928 0.2955 0.2317 0.013 Uiso 1 1 calc R . . C21 C 0.7925(6) 0.3709(4) 0.3182(4) 0.0132(11) Uani 1 1 d . . . H21 H 0.8587 0.386 0.3543 0.016 Uiso 1 1 calc R . . C22 C 0.6863(6) 0.4550(4) 0.3144(4) 0.0134(12) Uani 1 1 d . . . H22 H 0.7269 0.5144 0.2693 0.016 Uiso 1 1 calc R . . C23 C 0.6320(6) 0.4833(4) 0.4098(4) 0.0156(12) Uani 1 1 d . . . H23A H 0.6035 0.4235 0.4592 0.019 Uiso 1 1 calc R . . H23B H 0.5528 0.5301 0.4023 0.019 Uiso 1 1 calc R . . C24 C 0.7354(6) 0.5311(4) 0.4447(4) 0.0148(12) Uani 1 1 d . . . H24A H 0.7043 0.5328 0.5133 0.018 Uiso 1 1 calc R . . H24B H 0.8201 0.4896 0.441 0.018 Uiso 1 1 calc R . . C25 C 0.1986(7) 0.1534(5) 0.0678(5) 0.0212(14) Uani 1 1 d . . . C26 C 0.0665(8) 0.1704(7) 0.0395(7) 0.043(2) Uani 1 1 d . . . H26A H -0.002 0.1592 0.0974 0.064 Uiso 1 1 calc R . . H26B H 0.0582 0.1248 -0.0004 0.064 Uiso 1 1 calc R . . H26C H 0.055 0.2387 0.0025 0.064 Uiso 1 1 calc R . . C27 C 0.6569(6) 0.6438(5) 0.0754(5) 0.0207(14) Uani 1 1 d . . . C28 C 0.5497(7) 0.6369(6) 0.0257(5) 0.0296(16) Uani 1 1 d . . . H28A H 0.4685 0.6215 0.0728 0.044 Uiso 1 1 calc R . . H28B H 0.5738 0.5844 -0.0098 0.044 Uiso 1 1 calc R . . H28C H 0.5344 0.7 -0.0197 0.044 Uiso 1 1 calc R . . N1 N 0.2984(6) 0.1410(4) 0.0898(4) 0.0259(13) Uani 1 1 d . . . N2 N 0.7390(6) 0.6497(4) 0.1156(4) 0.0247(12) Uani 1 1 d . . . Br1 Br 0.82900(6) -0.06859(4) 0.19730(4) 0.01698(14) Uani 1 1 d . . . Br2 Br 0.70287(6) 0.18028(4) 0.11748(4) 0.01384(13) Uani 1 1 d . . . Br3 Br 0.23257(6) 0.05589(4) 0.54319(4) 0.01301(13) Uani 1 1 d . . . Br4 Br 0.03173(5) 0.11766(4) 0.35430(4) 0.01451(13) Uani 1 1 d . . . Br5 Br 0.21031(6) -0.12327(5) 0.11151(4) 0.01879(14) Uani 1 1 d . . . Br6 Br 0.38377(6) -0.30045(4) 0.26327(5) 0.01895(14) Uani 1 1 d . . . Br7 Br 0.61334(6) 0.72515(4) 0.43199(5) 0.01822(14) Uani 1 1 d . . . Br8 Br 0.91539(6) 0.67097(5) 0.52037(4) 0.01926(14) Uani 1 1 d . . . Br9 Br 1.17508(6) 0.60090(5) 0.05355(4) 0.01880(14) Uani 1 1 d . . . Br10 Br 1.21528(6) 0.35413(4) 0.19965(5) 0.01992(14) Uani 1 1 d . . . Br11 Br 0.72079(6) 0.24533(4) 0.39336(4) 0.01555(13) Uani 1 1 d . . . Br12 Br 0.53437(6) 0.42786(4) 0.26064(5) 0.02041(14) 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 C1 0.012(3) 0.015(3) 0.008(3) -0.001(2) -0.003(2) -0.001(2) C2 0.012(3) 0.018(3) 0.003(2) -0.003(2) 0.001(2) -0.004(2) C3 0.018(3) 0.012(3) 0.005(3) -0.001(2) -0.001(2) -0.001(2) C4 0.015(3) 0.018(3) 0.003(3) -0.002(2) -0.005(2) -0.001(2) C5 0.0118(13) 0.0110(13) 0.0096(14) -0.0029(9) -0.0015(9) -0.0009(9) C6 0.014(3) 0.012(3) 0.001(2) -0.001(2) -0.002(2) 0.003(2) C7 0.017(3) 0.015(3) 0.003(2) -0.002(2) 0.002(2) -0.004(2) C8 0.015(3) 0.017(3) 0.009(3) -0.007(2) -0.004(2) -0.004(2) C9 0.013(3) 0.015(3) 0.005(3) -0.005(2) -0.005(2) -0.002(2) C10 0.019(3) 0.004(2) 0.014(3) -0.001(2) -0.005(2) -0.001(2) C11 0.022(3) 0.015(3) 0.011(3) -0.008(2) 0.004(2) -0.005(2) C12 0.014(3) 0.016(3) 0.005(3) -0.005(2) 0.000(2) -0.005(2) C13 0.018(3) 0.009(3) 0.007(3) -0.002(2) -0.002(2) 0.001(2) C14 0.021(3) 0.014(3) 0.006(3) -0.002(2) -0.006(2) -0.002(2) C15 0.017(3) 0.016(3) 0.016(3) -0.005(2) -0.006(2) -0.002(2) C16 0.027(3) 0.009(3) 0.010(3) -0.005(2) -0.001(2) -0.001(2) C17 0.015(3) 0.019(3) 0.003(3) -0.001(2) 0.004(2) -0.004(2) C18 0.013(3) 0.009(3) 0.012(3) -0.001(2) -0.002(2) 0.003(2) C19 0.015(3) 0.019(3) 0.008(3) -0.002(2) -0.001(2) -0.003(2) C20 0.017(3) 0.013(3) 0.004(3) -0.006(2) 0.000(2) -0.002(2) C21 0.016(3) 0.010(3) 0.013(3) 0.000(2) -0.004(2) -0.004(2) C22 0.015(3) 0.015(3) 0.009(3) 0.001(2) -0.002(2) -0.004(2) C23 0.017(3) 0.009(3) 0.017(3) 0.000(2) 0.004(2) -0.005(2) C24 0.024(3) 0.011(3) 0.007(3) 0.001(2) 0.001(2) -0.002(2) C25 0.030(4) 0.017(3) 0.014(3) -0.002(2) 0.000(3) 0.001(3) C26 0.028(4) 0.048(5) 0.051(6) -0.008(4) -0.012(4) 0.001(3) C27 0.026(3) 0.016(3) 0.014(3) 0.005(2) 0.000(3) 0.001(2) C28 0.027(4) 0.039(4) 0.026(4) -0.009(3) -0.009(3) -0.005(3) N1 0.033(3) 0.022(3) 0.023(3) 0.002(2) -0.015(3) 0.000(2) N2 0.027(3) 0.021(3) 0.026(3) 0.000(2) -0.013(3) 0.004(2) Br1 0.0155(3) 0.0205(3) 0.0142(3) -0.0043(2) -0.0028(2) 0.0033(2) Br2 0.0201(3) 0.0142(3) 0.0056(3) -0.0002(2) 0.0018(2) -0.0060(2) Br3 0.0196(3) 0.0174(3) 0.0019(2) -0.0019(2) -0.0003(2) -0.0040(2) Br4 0.0136(3) 0.0152(3) 0.0134(3) -0.0006(2) -0.0033(2) 0.0008(2) Br5 0.0277(3) 0.0244(3) 0.0080(3) -0.0064(2) -0.0064(2) -0.0056(2) Br6 0.0241(3) 0.0102(3) 0.0224(3) -0.0033(2) -0.0030(2) -0.0035(2) Br7 0.0196(3) 0.0145(3) 0.0215(3) -0.0072(2) -0.0034(2) 0.0013(2) Br8 0.0311(3) 0.0204(3) 0.0104(3) -0.0083(2) -0.0121(2) 0.0068(2) Br9 0.0253(3) 0.0219(3) 0.0064(3) 0.0011(2) 0.0023(2) -0.0078(2) Br10 0.0195(3) 0.0182(3) 0.0196(3) -0.0030(2) -0.0014(2) 0.0030(2) Br11 0.0189(3) 0.0104(3) 0.0138(3) 0.0021(2) 0.0001(2) -0.0015(2) Br12 0.0220(3) 0.0163(3) 0.0265(3) -0.0050(3) -0.0135(3) 0.0001(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.523(8) . ? C1 C12 1.526(8) . ? C1 Br1 1.976(5) . ? C1 H1 1 . ? C2 C3 1.527(8) . ? C2 Br2 1.969(5) . ? C2 H2 1 . ? C3 C4 1.542(7) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C5 1.530(7) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.511(8) . ? C5 Br3 1.965(6) . ? C5 H5 1 . ? C6 C7 1.519(8) . ? C6 Br4 1.970(5) . ? C6 H6 1 . ? C7 C8 1.528(8) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 C9 1.536(8) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.519(7) . ? C9 Br5 1.954(5) . ? C9 H9 1 . ? C10 C11 1.525(8) . ? C10 Br6 1.975(5) . ? C10 H10 1 . ? C11 C12 1.541(8) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C14 1.521(8) . ? C13 C24 1.531(8) . ? C13 Br7 1.975(5) . ? C13 H13 1 . ? C14 C15 1.525(8) . ? C14 Br8 1.963(6) . ? C14 H14 1 . ? C15 C16 1.535(8) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.541(8) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.519(8) . ? C17 Br9 1.959(5) . ? C17 H17 1 . ? C18 C19 1.525(8) . ? C18 Br10 1.962(5) . ? C18 H18 1 . ? C19 C20 1.533(8) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 C21 1.525(8) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 C22 1.510(8) . ? C21 Br11 1.965(5) . ? C21 H21 1 . ? C22 C23 1.520(8) . ? C22 Br12 1.978(6) . ? C22 H22 1 . ? C23 C24 1.534(8) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C25 N1 1.111(9) . ? C25 C26 1.467(10) . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C27 N2 1.131(9) . ? C27 C28 1.447(10) . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? 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 C12 116.4(5) . . ? C2 C1 Br1 109.3(4) . . ? C12 C1 Br1 109.5(4) . . ? C2 C1 H1 107.1 . . ? C12 C1 H1 107.1 . . ? Br1 C1 H1 107.1 . . ? C1 C2 C3 114.2(5) . . ? C1 C2 Br2 110.2(4) . . ? C3 C2 Br2 106.7(4) . . ? C1 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? Br2 C2 H2 108.6 . . ? C2 C3 C4 113.2(5) . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 110.6(4) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 112.3(5) . . ? C6 C5 Br3 110.0(4) . . ? C4 C5 Br3 109.5(4) . . ? C6 C5 H5 108.3 . . ? C4 C5 H5 108.3 . . ? Br3 C5 H5 108.3 . . ? C5 C6 C7 116.3(4) . . ? C5 C6 Br4 110.0(4) . . ? C7 C6 Br4 108.5(4) . . ? C5 C6 H6 107.2 . . ? C7 C6 H6 107.2 . . ? Br4 C6 H6 107.2 . . ? C6 C7 C8 114.4(5) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C9 111.3(4) . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108 . . ? C10 C9 C8 115.6(5) . . ? C10 C9 Br5 112.0(4) . . ? C8 C9 Br5 109.8(4) . . ? C10 C9 H9 106.2 . . ? C8 C9 H9 106.2 . . ? Br5 C9 H9 106.2 . . ? C9 C10 C11 115.7(5) . . ? C9 C10 Br6 110.6(4) . . ? C11 C10 Br6 109.0(4) . . ? C9 C10 H10 107 . . ? C11 C10 H10 107 . . ? Br6 C10 H10 107 . . ? C10 C11 C12 112.5(5) . . ? 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 . . ? C1 C12 C11 113.7(5) . . ? C1 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C1 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C24 117.0(5) . . ? C14 C13 Br7 109.7(4) . . ? C24 C13 Br7 107.4(4) . . ? C14 C13 H13 107.4 . . ? C24 C13 H13 107.4 . . ? Br7 C13 H13 107.4 . . ? C13 C14 C15 113.9(5) . . ? C13 C14 Br8 110.9(4) . . ? C15 C14 Br8 107.8(4) . . ? C13 C14 H14 108 . . ? C15 C14 H14 108 . . ? Br8 C14 H14 108 . . ? C14 C15 C16 113.2(5) . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C15 C16 C17 111.6(5) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108 . . ? C18 C17 C16 112.3(4) . . ? C18 C17 Br9 110.4(4) . . ? C16 C17 Br9 109.7(4) . . ? C18 C17 H17 108.1 . . ? C16 C17 H17 108.1 . . ? Br9 C17 H17 108.1 . . ? C17 C18 C19 116.5(5) . . ? C17 C18 Br10 109.7(4) . . ? C19 C18 Br10 109.9(4) . . ? C17 C18 H18 106.7 . . ? C19 C18 H18 106.7 . . ? Br10 C18 H18 106.7 . . ? C18 C19 C20 113.9(5) . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C21 C20 C19 113.9(5) . . ? C21 C20 H20A 108.8 . . ? C19 C20 H20A 108.8 . . ? C21 C20 H20B 108.8 . . ? C19 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 115.9(5) . . ? C22 C21 Br11 111.5(4) . . ? C20 C21 Br11 109.9(4) . . ? C22 C21 H21 106.3 . . ? C20 C21 H21 106.3 . . ? Br11 C21 H21 106.3 . . ? C21 C22 C23 115.6(5) . . ? C21 C22 Br12 111.5(4) . . ? C23 C22 Br12 108.1(4) . . ? C21 C22 H22 107.1 . . ? C23 C22 H22 107.1 . . ? Br12 C22 H22 107.1 . . ? C22 C23 C24 112.1(5) . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23B 109.2 . . ? C24 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C13 C24 C23 113.3(5) . . ? C13 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? C13 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? N1 C25 C26 179.4(8) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N2 C27 C28 178.8(8) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? data_compound_TBCD-5 _database_code_depnum_ccdc_archive 'CCDC 261487' _audit_creation_method 'manually at CCDC' _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_sum 'C12 H18 Br4' _chemical_formula_moiety ? _chemical_formula_weight 481.89 _chemical_melting_point ? _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_Int_Tables_number ? loop_ _symmetry_equiv_pos_as_xyz '0.5+x, 0.5-y, 0.5-z' '-x, 0.5+y, 0.5-z' '0.5-x, -y, 0.5+z' _cell_length_a 17.163(2) _cell_length_b 12.517(1) _cell_length_c 14.250(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3061.32 _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 2.09 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_special_details ; ? ; _exptl_absorpt_correction_type psi-scan _exptl_absorpt_coefficient_mu 103.95 _exptl_crystal_F_000 1840 _diffrn_ambient_temperature 219 _diffrn_radiation_probe x-ray _diffrn_radiation_type Mok\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_number 3112 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_av_R_equivalents ? _reflns_number_total 2691 _reflns_observed_criterion Fo>3\s(Fo) _reflns_number_gt 1125 _refine_ls_R_factor_gt 0.068 _refine_ls_wR_factor_ref 0.087 _refine_ls_number_reflns 1125 _refine_ls_hydrogen_treatment ? _refine_ls_number_parameters 166 _refine_ls_number_restraints ? _refine_special_details ; ? ; _refine_diff_density_max ? _refine_diff_density_min ? loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z Br1 0.1878(1) -0.1269(2) 0.0790(2) Br2 0.3293(1) 0.0619(2) 0.1312(2) Br3 -0.0187(1) 0.0709(2) 0.1435(2) Br4 -0.0458(2) 0.3566(2) 0.1628(2) C1 0.1952(12) 0.0141(15) 0.0190(13) C2 0.2240(11) 0.0972(16) 0.0861(14) C3 0.1715(12) 0.1270(18) 0.1678(15) C4 0.1112(12) 0.2124(16) 0.1438(14) C5 0.0404(11) 0.1826(15) 0.0811(13) C6 -0.0094(12) 0.2746(15) 0.0539(13) C7 0.0269(13) 0.3529(17) -0.0138(15) C8 0.0558(15) 0.3049(21) -0.1076(16) C9 0.1337(11) 0.2536(18) -0.1020(14) C10 0.1548(12) 0.1596(17) -0.1353(14) C11 0.2354(14) 0.1100(20) -0.1289(18) C12 0.2368(12) 0.0050(18) -0.0747(15) H11 0.1387(80) 0.0154(107) 0.0128(90) H21 0.2429(91) 0.1493(139) 0.0462(108) H31 0.1468(77) 0.0723(113) 0.1857(92) H32 0.2012(67) 0.1581(92) 0.2365(84) H41 0.0854(68) 0.2096(92) 0.2078(96) H42 0.1392(96) 0.2789(141) 0.1258(108) H51 0.0501(194) 0.1542(288) 0.0232(255) H61 -0.0211(107) 0.4058(144) -0.0276(276) H72 0.0850(82) 0.3830(108) 0.0029(98) H81 0.0549(104) 0.3788(141) -0.1600(118) H82 0.0208(79) 0.2639(101) -0.1092(81) H91 0.1791(118) 0.2978(147) -0.0589(143) H101 0.1158(102) 0.1158(132) -0.1754(107) H111 0.2781(93) 0.1588(133) -0.0833(108) H112 0.2592(157) 0.0997(207) -0.1847(166) H121 0.3054(72) -0.0015(95) -0.0704(88) H122 0.2198(125) -0.0364(182) -0.1169(133) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 Br1 1.964(1) C5 Br3 1.943(1) C2 Br2 1.969(22) C8 Br4 1.963(21) C2 C1 1.497(28) C12 C1 1.519(31) C3 C2 1.519(29) C4 C3 1.527(30) C5 C4 1.554(30) C6 C5 1.486(27) C7 C6 1.509(29) C8 C7 1.547(33) C9 C8 1.485(31) C10 C9 1.318(30) C11 C10 1.519(34) C12 C11 1.525(34) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 ? ? ? ? ? ? ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle ? ? ? ? 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 ? ? ? ? ? #END #END data_compound_hbcd-1 _database_code_depnum_ccdc_archive 'CCDC 261488' _audit_creation_method 'manually at CCDC' _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_sum 'C12 H18 Br6' _chemical_formula_moiety ? _chemical_formula_weight 641.73 _chemical_melting_point ? _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz '0.5+x, 0.5-y, 0.5-z' '-x, 0.5+y, 0.5-z' '0.5-x, -y, 0.5+z' _cell_length_a 11.670(2) _cell_length_b 28.998(6) _cell_length_c 10.483(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3547.52(6) _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 1.207 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_special_details ; ? ; _exptl_absorpt_correction_type psi-scan _exptl_absorpt_coefficient_mu 133.01 _exptl_crystal_F_000 2336 _diffrn_ambient_temperature 219.0 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_number 3613 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_av_R_equivalents ? _reflns_number_total 1740 _reflns_observed_criterion Fo>3\s(Fo) _reflns_number_gt 1358 _refine_ls_R_factor_gt 0.054 _refine_ls_wR_factor_ref 0.072 _refine_ls_number_reflns 1358 _refine_ls_hydrogen_treatment ? _refine_ls_number_parameters 103 _refine_ls_number_restraints ? _refine_special_details ; ? ; _refine_diff_density_max ? _refine_diff_density_min ? loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z BR1 0.07002 0.01497 0.33659 BR2 0.35612 -0.00438 0.42888 BR3 0.11110 -0.15643 0.86825 BR4 0.28357 -0.23608 0.68592 BR5 -0.10747 -0.12676 0.44005 BR6 -0.05473 -0.17649 0.14518 C1 0.13170 -0.04637 0.39416 C2 0.22274 -0.03678 0.49775 C3 0.26023 -0.07979 0.56725 C4 0.16524 -0.09696 0.66145 C5 0.20645 -0.14350 0.71714 C6 0.19378 -0.18475 0.62060 C7 0.06958 -0.19921 0.59112 C8 0.05341 -0.20200 0.44179 C9 0.04050 -0.15269 0.39414 C10 0.06725 -0.14726 0.25078 C11 0.07375 -0.09517 0.20237 C12 0.17816 -0.07166 0.27795 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C1 2.012 Br2 C2 1.956 Br3 C5 1.972 Br4 C6 1.945 Br5 C9 1.944 Br6 C10 1.993 C1 C2 1.544 C1 C12 1.522 C2 C3 1.509 C3 C4 1.566 C4 C5 1.547 C5 C6 1.574 C6 C7 1.540 C7 C8 1.579 C8 C9 1.522 C9 C10 1.543 C10 C11 1.595 C11 C12 1.605 #END