#------------------------------------------------------------------------------ #$Date: 2011-11-02 19:57:34 +0200 (Wed, 02 Nov 2011) $ #$Revision: 29029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/8103100.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_8103100 loop_ _publ_author_name 'Wenxiu Sun' 'Qilong Hu' 'Chunming Ding' 'Yan Duan' 'Jingwen Jia' _publ_section_title ; Crystal structure of 2-acetamido-5-bromobenzoic acid, C9H8BrNO3 ; _journal_issue 1 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 75 _journal_volume 226 _journal_year 2011 _chemical_formula_sum 'C9 H8 Br N O3' _chemical_formula_weight 258.07 _chemical_name_systematic ; 2-acetamido-5-bromo benzoic acid ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 113.129(13) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 14.919(4) _cell_length_b 9.333(2) _cell_length_c 15.508(4) _cell_measurement_reflns_used 1810 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 24.65 _cell_measurement_theta_min 2.64 _cell_volume 1985.8(9) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4729 _diffrn_reflns_theta_full 24.65 _diffrn_reflns_theta_max 24.65 _diffrn_reflns_theta_min 2.64 _exptl_absorpt_coefficient_mu 4.120 _exptl_absorpt_correction_T_max 0.3881 _exptl_absorpt_correction_T_min 0.2902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 1024 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.579 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.071 _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 1683 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.085 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0382 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+4.1963P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0951 _refine_ls_wR_factor_ref 0.1005 _reflns_number_gt 1385 _reflns_number_total 1683 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file 1267-3297.cff _[local]_cod_data_source_block global _[local]_cod_cif_authors_sg_H-M C2/c _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 8103100 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' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 Br1 Br 0.35211(3) 1.03064(6) 0.20033(4) 0.0670(2) Uani 1 1 d . O3 O -0.1453(2) 1.1214(3) 0.10082(19) 0.0477(7) Uani 1 1 d . N1 N -0.0741(2) 0.9045(4) 0.1067(2) 0.0405(7) Uani 1 1 d . C7 C 0.0226(2) 0.9420(4) 0.1222(2) 0.0341(8) Uani 1 1 d . C5 C 0.1612(3) 1.0979(5) 0.1855(3) 0.0448(9) Uani 1 1 d . C3 C 0.1770(3) 0.8729(4) 0.1190(2) 0.0360(8) Uani 1 1 d . C8 C -0.1494(3) 0.9919(4) 0.0994(2) 0.0378(8) Uani 1 1 d . C4 C 0.2169(3) 0.9981(4) 0.1640(3) 0.0401(9) Uani 1 1 d . C2 C 0.0788(2) 0.8438(4) 0.0968(2) 0.0326(8) Uani 1 1 d . C6 C 0.0638(3) 1.0700(4) 0.1643(3) 0.0420(9) Uani 1 1 d . C9 C -0.2410(3) 0.9127(5) 0.0877(3) 0.0544(11) Uani 1 1 d . H9A H -0.2700 0.9557 0.1267 0.082 Uiso 1 1 calc R H9B H -0.2256 0.8144 0.1055 0.082 Uiso 1 1 calc R H9C H -0.2858 0.9175 0.0233 0.082 Uiso 1 1 calc R O1 O -0.02043(18) 0.6376(3) 0.07388(19) 0.0467(7) Uani 1 1 d . O2 O 0.0687(2) 0.6595(3) -0.0141(2) 0.0657(8) Uani 1 1 d . H2 H 0.0432 0.5823 -0.0350 0.099 Uiso 1 1 calc R C1 C 0.0377(2) 0.7049(4) 0.0513(2) 0.0335(8) Uani 1 1 d . H1 H -0.081(3) 0.808(5) 0.105(3) 0.049(12) Uiso 1 1 d . H3 H 0.211(3) 0.805(4) 0.103(2) 0.036(10) Uiso 1 1 d . H5 H 0.190(3) 1.188(5) 0.217(3) 0.053(11) Uiso 1 1 d . H6 H 0.030(3) 1.140(5) 0.183(3) 0.053(12) Uiso 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 Br1 0.0372(3) 0.0721(4) 0.0875(4) -0.0122(3) 0.0199(2) -0.0187(2) O3 0.0554(16) 0.0321(15) 0.0646(17) 0.0036(13) 0.0335(14) 0.0041(12) N1 0.0370(17) 0.0286(18) 0.058(2) -0.0047(15) 0.0211(14) -0.0023(14) C7 0.0355(18) 0.030(2) 0.0392(18) 0.0011(15) 0.0172(15) -0.0022(14) C5 0.049(2) 0.042(2) 0.043(2) -0.0087(18) 0.0176(18) -0.0125(19) C3 0.0346(18) 0.035(2) 0.0389(19) 0.0004(16) 0.0152(16) -0.0006(15) C8 0.041(2) 0.037(2) 0.0396(19) -0.0011(16) 0.0203(16) 0.0022(16) C4 0.0337(18) 0.044(2) 0.043(2) -0.0006(17) 0.0145(15) -0.0113(16) C2 0.0339(18) 0.0294(19) 0.0350(18) 0.0025(14) 0.0141(14) -0.0016(14) C6 0.047(2) 0.036(2) 0.048(2) -0.0073(17) 0.0236(18) -0.0022(17) C9 0.041(2) 0.045(2) 0.079(3) -0.004(2) 0.026(2) 0.0025(19) O1 0.0444(15) 0.0343(14) 0.0738(18) -0.0067(13) 0.0364(14) -0.0106(11) O2 0.070(2) 0.051(2) 0.083(2) -0.0108(17) 0.0366(18) -0.0065(16) C1 0.0307(17) 0.0278(19) 0.043(2) -0.0002(15) 0.0157(15) 0.0025(14) 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' N N 0.0061 0.0033 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C8 N1 C7 128.5(3) C8 N1 H1 121(3) C7 N1 H1 111(3) C6 C7 C2 119.6(3) C6 C7 N1 122.0(3) C2 C7 N1 118.4(3) C4 C5 C6 119.6(4) C4 C5 H5 121(2) C6 C5 H5 120(2) C4 C3 C2 119.8(3) C4 C3 H3 124(2) C2 C3 H3 116(2) O3 C8 N1 124.4(3) O3 C8 C9 122.1(3) N1 C8 C9 113.5(3) C3 C4 C5 121.2(3) C3 C4 Br1 119.2(3) C5 C4 Br1 119.6(3) C3 C2 C7 119.4(3) C3 C2 C1 119.0(3) C7 C2 C1 121.6(3) C5 C6 C7 120.4(4) C5 C6 H6 116(3) C7 C6 H6 124(3) C8 C9 H9A 109.5 C8 C9 H9B 109.5 H9A C9 H9B 109.5 C8 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C1 O2 H2 109.5 O1 C1 O2 123.2(3) O1 C1 C2 121.1(3) O2 C1 C2 115.7(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C4 1.894(4) O3 C8 1.210(4) N1 C8 1.357(5) N1 C7 1.410(5) N1 H1 0.90(5) C7 C6 1.384(5) C7 C2 1.400(5) C5 C4 1.373(6) C5 C6 1.383(5) C5 H5 0.98(4) C3 C4 1.371(5) C3 C2 1.393(5) C3 H3 0.90(4) C8 C9 1.499(5) C2 C1 1.488(5) C6 H6 0.94(4) C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 O1 C1 1.228(4) O2 C1 1.339(4) O2 H2 0.8200 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 C8 N1 C7 C6 23.3(6) C8 N1 C7 C2 -158.9(3) C7 N1 C8 O3 3.8(6) C7 N1 C8 C9 -177.0(3) C2 C3 C4 C5 -1.8(6) C2 C3 C4 Br1 176.2(3) C6 C5 C4 C3 2.2(6) C6 C5 C4 Br1 -175.9(3) C4 C3 C2 C7 -1.1(5) C4 C3 C2 C1 -177.7(3) C6 C7 C2 C3 3.6(5) N1 C7 C2 C3 -174.3(3) C6 C7 C2 C1 -180.0(3) N1 C7 C2 C1 2.2(5) C4 C5 C6 C7 0.4(6) C2 C7 C6 C5 -3.2(6) N1 C7 C6 C5 174.6(3) C3 C2 C1 O1 139.6(3) C7 C2 C1 O1 -36.9(5) C3 C2 C1 O2 -40.0(5) C7 C2 C1 O2 143.5(3)