# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 892370' #TrackingRef 'web_deposit_cif_file_0_FushunLiang_1342496409.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H11 Br2 Cl O' _chemical_formula_sum 'C15 H11 Br2 Cl O' _chemical_formula_weight 402.51 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' Cl Cl 0.1484 0.1585 '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 b c a' _symmetry_space_group_name_hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 5.871(5) _cell_length_b 16.844(5) _cell_length_c 29.189(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 2887(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2831 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 25.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.852 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 5.790 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2245 _exptl_absorpt_correction_T_max 0.3060 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14394 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2831 _reflns_number_gt 1875 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0246P)^2^+2.4964P] 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 0.00010(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2831 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 Cl1 Cl 0.1255(2) -0.25356(7) 0.71095(4) 0.0555(3) Uani 1 1 d . . . Br1 Br 0.46952(10) 0.02119(3) 0.561976(16) 0.05976(19) Uani 1 1 d . . . Br2 Br 0.79296(9) 0.08699(3) 0.701111(16) 0.05018(16) Uani 1 1 d . . . C1 C 0.2915(8) -0.1735(2) 0.69392(13) 0.0355(10) Uani 1 1 d . . . C2 C 0.4964(8) -0.1872(2) 0.67287(14) 0.0403(11) Uani 1 1 d . . . H2A H 0.5487 -0.2388 0.6686 0.048 Uiso 1 1 calc R . . C3 C 0.6246(7) -0.1233(2) 0.65803(14) 0.0369(10) Uani 1 1 d . . . H3A H 0.7634 -0.1322 0.6436 0.044 Uiso 1 1 calc R . . C4 C 0.5496(7) -0.0463(2) 0.66432(13) 0.0324(9) Uani 1 1 d . . . C5 C 0.3426(7) -0.0347(2) 0.68609(14) 0.0410(11) Uani 1 1 d . . . H5A H 0.2901 0.0168 0.6906 0.049 Uiso 1 1 calc R . . C6 C 0.2125(8) -0.0974(2) 0.70118(14) 0.0418(10) Uani 1 1 d . . . H6A H 0.0744 -0.0886 0.7160 0.050 Uiso 1 1 calc R . . C7 C 0.6926(7) 0.0218(2) 0.64792(13) 0.0379(10) Uani 1 1 d . . . H7A H 0.8281 0.0003 0.6328 0.045 Uiso 1 1 calc R . . C8 C 0.5816(7) 0.0800(2) 0.61613(13) 0.0367(10) Uani 1 1 d . . . H8A H 0.4551 0.1070 0.6316 0.044 Uiso 1 1 calc R . . C9 C 0.7461(8) 0.1407(2) 0.59575(14) 0.0409(11) Uani 1 1 d . . . C10 C 0.6584(7) 0.2166(2) 0.57712(13) 0.0338(10) Uani 1 1 d . . . C11 C 0.8033(8) 0.2603(2) 0.54871(14) 0.0443(11) Uani 1 1 d . . . H11A H 0.9464 0.2404 0.5413 0.053 Uiso 1 1 calc R . . C12 C 0.7359(9) 0.3323(3) 0.53170(15) 0.0537(13) Uani 1 1 d . . . H12A H 0.8318 0.3603 0.5122 0.064 Uiso 1 1 calc R . . C13 C 0.5281(9) 0.3632(3) 0.54331(16) 0.0536(13) Uani 1 1 d . . . H13A H 0.4847 0.4126 0.5321 0.064 Uiso 1 1 calc R . . C14 C 0.3833(8) 0.3218(3) 0.57141(15) 0.0485(12) Uani 1 1 d . . . H14A H 0.2430 0.3433 0.5795 0.058 Uiso 1 1 calc R . . C15 C 0.4468(7) 0.2478(2) 0.58769(14) 0.0400(10) Uani 1 1 d . . . H15A H 0.3465 0.2190 0.6059 0.048 Uiso 1 1 calc R . . O1 O 0.9476(6) 0.1243(2) 0.59438(13) 0.0715(11) 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 Cl1 0.0630(8) 0.0472(7) 0.0563(7) 0.0098(5) 0.0057(6) -0.0197(6) Br1 0.0960(5) 0.0381(3) 0.0452(3) 0.0026(2) -0.0192(3) -0.0070(3) Br2 0.0575(3) 0.0402(3) 0.0528(3) -0.0052(2) -0.0128(2) -0.0043(2) C1 0.041(3) 0.032(2) 0.033(2) 0.0022(17) -0.001(2) -0.0033(19) C2 0.053(3) 0.026(2) 0.043(2) 0.0034(18) 0.002(2) 0.004(2) C3 0.036(2) 0.032(2) 0.043(2) 0.0029(19) 0.008(2) 0.0061(19) C4 0.034(2) 0.027(2) 0.036(2) 0.0046(17) -0.0014(18) 0.0032(18) C5 0.042(3) 0.027(2) 0.054(3) -0.0009(19) 0.006(2) 0.0071(19) C6 0.037(2) 0.044(3) 0.044(2) 0.002(2) 0.006(2) 0.001(2) C7 0.042(3) 0.029(2) 0.042(2) 0.0001(18) 0.001(2) 0.003(2) C8 0.043(3) 0.026(2) 0.042(2) -0.0014(18) 0.007(2) -0.0001(18) C9 0.041(3) 0.032(2) 0.049(3) 0.0023(19) 0.011(2) -0.002(2) C10 0.037(3) 0.030(2) 0.034(2) 0.0023(17) 0.0026(19) -0.0041(18) C11 0.049(3) 0.038(3) 0.045(2) -0.001(2) 0.010(2) -0.008(2) C12 0.070(4) 0.046(3) 0.045(3) 0.012(2) 0.008(3) -0.012(3) C13 0.070(4) 0.036(3) 0.055(3) 0.009(2) -0.009(3) -0.005(3) C14 0.046(3) 0.044(3) 0.055(3) 0.007(2) -0.003(2) 0.005(2) C15 0.040(3) 0.034(2) 0.045(2) 0.008(2) 0.003(2) -0.007(2) O1 0.044(2) 0.058(2) 0.112(3) 0.027(2) 0.024(2) 0.0110(17) _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 Cl1 C1 1.736(4) . ? Br1 C8 1.978(4) . ? Br2 C7 1.991(4) . ? C1 C2 1.371(6) . ? C1 C6 1.381(5) . ? C2 C3 1.383(5) . ? C3 C4 1.381(5) . ? C4 C5 1.385(5) . ? C4 C7 1.499(5) . ? C5 C6 1.375(6) . ? C7 C8 1.499(5) . ? C8 C9 1.527(5) . ? C9 O1 1.216(5) . ? C9 C10 1.481(6) . ? C10 C15 1.384(6) . ? C10 C11 1.398(5) . ? C11 C12 1.369(6) . ? C12 C13 1.370(7) . ? C13 C14 1.372(6) . ? C14 C15 1.385(6) . ? 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 121.3(4) . . ? C2 C1 Cl1 119.4(3) . . ? C6 C1 Cl1 119.3(3) . . ? C1 C2 C3 119.2(4) . . ? C4 C3 C2 121.0(4) . . ? C3 C4 C5 118.2(4) . . ? C3 C4 C7 119.8(4) . . ? C5 C4 C7 122.0(4) . . ? C6 C5 C4 121.7(4) . . ? C5 C6 C1 118.5(4) . . ? C8 C7 C4 117.0(4) . . ? C8 C7 Br2 104.5(3) . . ? C4 C7 Br2 109.8(3) . . ? C7 C8 C9 113.8(4) . . ? C7 C8 Br1 108.1(3) . . ? C9 C8 Br1 103.5(3) . . ? O1 C9 C10 121.5(4) . . ? O1 C9 C8 118.5(4) . . ? C10 C9 C8 120.0(4) . . ? C15 C10 C11 118.6(4) . . ? C15 C10 C9 124.0(4) . . ? C11 C10 C9 117.4(4) . . ? C12 C11 C10 120.4(4) . . ? C11 C12 C13 120.3(4) . . ? C12 C13 C14 120.5(4) . . ? C13 C14 C15 119.7(5) . . ? C10 C15 C14 120.5(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.592 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.132