#------------------------------------------------------------------------------ #$Date: 2016-03-23 16:03:23 +0200 (Wed, 23 Mar 2016) $ #$Revision: 179360 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/32/57/4325710.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4325710 loop_ _publ_author_name 'Stefan Durben' 'Thomas Baumgartner' _publ_contact_author_address ; Department of Chemistry University of Calgary 2500 University Drive N.W. Calgary, Alberta, Canada T2N 1N4 ; _publ_contact_author_email thomas.baumgartner@ucalgary.ca _publ_contact_author_name 'Baumgartner, Thomas' _publ_contact_author_phone (403)220-3039 _publ_section_title ; Azadibenzophospholes: Functional Building Blocks with Pronounced Electron-Acceptor Character ; _journal_name_full 'Inorganic Chemistry' _journal_page_first 6823 _journal_page_last 6836 _journal_paper_doi 10.1021/ic200951x _journal_volume 50 _journal_year 2011 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C11 H7 Br2 N' _chemical_formula_sum 'C11 H7 Br2 N' _chemical_formula_weight 312.98 _chemical_name_common sd104 _chemical_name_systematic ; 3-Bromo-4-(2-bromophenyl)pyridine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2011-02-23T10:10:00-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90.00 _cell_angle_beta 130.860(18) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.7205(7) _cell_length_b 10.9312(9) _cell_length_c 12.9728(9) _cell_measurement_reflns_used 2030 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.485 _cell_measurement_theta_min 0.998 _cell_volume 1042.5(3) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.97 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_UB_11 -0.0352192 _diffrn_orient_matrix_UB_12 0.0746392 _diffrn_orient_matrix_UB_13 0.0430022 _diffrn_orient_matrix_UB_21 0.0271104 _diffrn_orient_matrix_UB_22 0.0512101 _diffrn_orient_matrix_UB_23 -0.0761961 _diffrn_orient_matrix_UB_31 -0.0936756 _diffrn_orient_matrix_UB_32 -0.0132415 _diffrn_orient_matrix_UB_33 -0.0522866 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_unetI/netI 0.0378 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 3043 _diffrn_reflns_theta_full 25 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.14 _exptl_absorpt_coefficient_mu 7.732 _exptl_absorpt_correction_T_max 0.6294 _exptl_absorpt_correction_T_min 0.4808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Denzo and Scalepack' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.994 _exptl_crystal_description blade _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.824 _refine_diff_density_min -0.77 _refine_diff_density_rms 0.148 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_hydrogen_treatment riding _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 2322 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.097 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.057 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+8.3863P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1223 _refine_ls_wR_factor_ref 0.1354 _reflns_number_gt 1884 _reflns_number_total 2322 _reflns_threshold_expression >2\s(I) _cod_data_source_file ic200951x_si_002_4.cif _cod_data_source_block cmpd12 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 4325710 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 C2 C 0.0727(8) 0.1360(6) 0.6905(6) 0.0332(14) Uani 1 1 d . C3 C -0.0442(9) 0.1603(7) 0.5527(7) 0.0410(16) Uani 1 1 d . H3 H -0.0108 0.1357 0.5031 0.049 Uiso 1 1 calc R C4 C -0.2456(10) 0.2518(7) 0.5611(7) 0.0479(19) Uani 1 1 d . H4 H -0.3565 0.2911 0.5164 0.057 Uiso 1 1 calc R C5 C -0.1368(9) 0.2332(7) 0.6992(7) 0.0406(16) Uani 1 1 d . H5 H -0.1744 0.2593 0.7456 0.049 Uiso 1 1 calc R Br2 Br 0.28986(9) 0.04897(7) 0.77095(7) 0.0401(2) Uani 1 1 d . N1 N -0.2019(8) 0.2170(6) 0.4877(6) 0.0461(15) Uani 1 1 d . C11 C 0.1550(8) 0.1544(6) 0.9186(6) 0.0302(13) Uani 1 1 d . C12 C 0.2880(9) 0.2386(6) 1.0131(6) 0.0337(14) Uani 1 1 d . C13 C 0.4068(9) 0.2150(7) 1.1504(7) 0.0380(15) Uani 1 1 d . H13 H 0.4961 0.2718 1.2113 0.046 Uiso 1 1 calc R C14 C 0.3932(10) 0.1064(7) 1.1980(7) 0.0412(16) Uani 1 1 d . H14 H 0.4717 0.091 1.2912 0.049 Uiso 1 1 calc R C15 C 0.2641(10) 0.0212(7) 1.1081(7) 0.0420(16) Uani 1 1 d . H15 H 0.2558 -0.052 1.1402 0.05 Uiso 1 1 calc R C16 C 0.1454(9) 0.0448(7) 0.9681(7) 0.0380(15) Uani 1 1 d . H16 H 0.059 -0.0134 0.9074 0.046 Uiso 1 1 calc R C1 C 0.0298(8) 0.1750(6) 0.7687(7) 0.0324(13) Uani 1 1 d . Br1 Br 0.30546(11) 0.38963(7) 0.95035(8) 0.0467(2) 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 C2 0.027(3) 0.032(3) 0.031(3) -0.003(3) 0.015(3) -0.005(2) C3 0.040(4) 0.040(4) 0.031(3) 0.000(3) 0.018(3) -0.008(3) C4 0.031(4) 0.048(4) 0.033(4) 0.003(3) 0.007(3) 0.005(3) C5 0.034(3) 0.036(4) 0.042(4) 0.001(3) 0.020(3) 0.005(3) Br2 0.0368(4) 0.0456(4) 0.0397(4) 0.0018(3) 0.0259(3) 0.0039(3) N1 0.040(3) 0.041(3) 0.026(3) 0.003(3) 0.008(3) -0.003(3) C11 0.027(3) 0.030(3) 0.027(3) -0.001(2) 0.015(3) 0.007(2) C12 0.031(3) 0.039(4) 0.029(3) 0.006(3) 0.019(3) 0.006(3) C13 0.037(3) 0.037(4) 0.031(3) -0.006(3) 0.019(3) 0.002(3) C14 0.037(4) 0.051(4) 0.029(3) 0.003(3) 0.019(3) 0.010(3) C15 0.042(4) 0.043(4) 0.040(4) 0.011(3) 0.026(3) 0.007(3) C16 0.028(3) 0.040(4) 0.033(3) -0.003(3) 0.014(3) 0.000(3) C1 0.028(3) 0.024(3) 0.034(3) -0.004(2) 0.015(3) -0.003(2) Br1 0.0503(4) 0.0388(4) 0.0429(4) -0.0031(3) 0.0269(4) -0.0083(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 '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' Br Br -0.29 2.46 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C3 C2 C1 120.1(6) C3 C2 Br2 119.2(5) C1 C2 Br2 120.7(5) N1 C3 C2 123.0(7) N1 C3 H3 118.5 C2 C3 H3 118.5 N1 C4 C5 123.9(7) N1 C4 H4 118.1 C5 C4 H4 118.1 C4 C5 C1 119.4(7) C4 C5 H5 120.3 C1 C5 H5 120.3 C3 N1 C4 117.3(6) C16 C11 C12 117.8(6) C16 C11 C1 119.3(6) C12 C11 C1 122.9(6) C13 C12 C11 121.7(6) C13 C12 Br1 119.0(5) C11 C12 Br1 119.2(5) C12 C13 C14 119.7(7) C12 C13 H13 120.2 C14 C13 H13 120.2 C15 C14 C13 120.2(6) C15 C14 H14 119.9 C13 C14 H14 119.9 C14 C15 C16 119.8(7) C14 C15 H15 120.1 C16 C15 H15 120.1 C11 C16 C15 120.7(6) C11 C16 H16 119.6 C15 C16 H16 119.6 C5 C1 C2 116.4(6) C5 C1 C11 121.8(6) C2 C1 C11 121.8(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C2 C3 1.378(9) C2 C1 1.393(9) C2 Br2 1.889(6) C3 N1 1.325(9) C3 H3 0.93 C4 N1 1.326(10) C4 C5 1.375(10) C4 H4 0.93 C5 C1 1.389(9) C5 H5 0.93 C11 C16 1.391(10) C11 C12 1.395(9) C11 C1 1.489(8) C12 C13 1.372(9) C12 Br1 1.897(7) C13 C14 1.384(10) C13 H13 0.93 C14 C15 1.374(11) C14 H14 0.93 C15 C16 1.397(9) C15 H15 0.93 C16 H16 0.93 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 C1 C2 C3 N1 -2.1(11) Br2 C2 C3 N1 177.6(5) N1 C4 C5 C1 0.2(12) C2 C3 N1 C4 0.5(11) C5 C4 N1 C3 0.5(12) C16 C11 C12 C13 0.4(9) C1 C11 C12 C13 -177.1(6) C16 C11 C12 Br1 -179.7(5) C1 C11 C12 Br1 2.8(8) C11 C12 C13 C14 -1.5(10) Br1 C12 C13 C14 178.6(5) C12 C13 C14 C15 1.5(10) C13 C14 C15 C16 -0.5(11) C12 C11 C16 C15 0.7(10) C1 C11 C16 C15 178.3(6) C14 C15 C16 C11 -0.7(10) C4 C5 C1 C2 -1.7(10) C4 C5 C1 C11 178.8(7) C3 C2 C1 C5 2.6(9) Br2 C2 C1 C5 -177.0(5) C3 C2 C1 C11 -178.0(6) Br2 C2 C1 C11 2.4(8) C16 C11 C1 C5 92.7(8) C12 C11 C1 C5 -89.9(8) C16 C11 C1 C2 -86.7(8) C12 C11 C1 C2 90.7(8)