#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/02/2240215.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240215
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Melo, Vanessa'
'Ellena, Javier'
_publ_section_title
;
 Crystal structure of 4-bromo-N-(2-hydroxyphenyl)benzamide
;
_journal_coeditor_code           SU5019
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1261
_journal_page_last               o1262
_journal_paper_doi               10.1107/S1600536814024696
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C13 H10 Br N O2'
_chemical_formula_sum            'C13 H10 Br N O2'
_chemical_formula_weight         292.13
_chemical_melting_point          454.0(10)
_chemical_name_common            4-bromo-N-(2-hydroxyphenyl)benzamide
_chemical_name_systematic
;
4-Bromo-N-(2-hydroxyphenyl)benzamide
;
_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_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.0080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.4258(10)
_cell_length_b                   5.64730(10)
_cell_length_c                   9.2464(3)
_cell_measurement_reflns_used    2490
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.376
_cell_measurement_theta_min      3.484
_cell_volume                     1221.54(7)
_computing_cell_refinement
;
SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Nonius, 2000)
;
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0632
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21458
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_min         3.484
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.353
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.129
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.677
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0999P)²+0.5651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1680
_reflns_number_gt                1664
_reflns_number_total             2490
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su5019sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2240215
_cod_database_fobs_code          2240215
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Br Br1 0.46192(2) 1.31657(9) 0.85256(8) 0.1081(3) Uani d 1
O O1 0.23094(11) 0.5820(4) 0.8853(2) 0.0546(6) Uani d 1
C C7 0.24418(16) 0.7116(6) 0.7843(3) 0.0462(8) Uani d 1
C C9 0.15972(16) 0.4064(6) 0.5411(4) 0.0513(8) Uani d 1
O O2 0.20914(13) 0.3579(5) 0.4767(3) 0.0700(8) Uani d 1
H HO2 0.2040 0.2472 0.4201 0.105 Uiso calc 1
N N1 0.21228(13) 0.7256(5) 0.6607(3) 0.0520(7) Uani d 1
H H1 0.2235 0.8168 0.5933 0.062 Uiso calc 1
C C1 0.29740(16) 0.8587(6) 0.7961(3) 0.0490(8) Uani d 1
C C6 0.30259(17) 1.0664(6) 0.7177(4) 0.0565(9) Uani d 1
H H6 0.2728 1.1161 0.6543 0.068 Uiso calc 1
C C8 0.16058(15) 0.5964(6) 0.6357(3) 0.0500(8) Uani d 1
C C5 0.3522(2) 1.1998(7) 0.7340(5) 0.0675(11) Uani d 1
H H5 0.3560 1.3385 0.6811 0.081 Uiso calc 1
C C2 0.34181(18) 0.7886(7) 0.8900(4) 0.0604(9) Uani d 1
H H2 0.3384 0.6499 0.9431 0.073 Uiso calc 1
C C4 0.39549(18) 1.1262(7) 0.8281(5) 0.0665(10) Uani d 1
C C13 0.1110(2) 0.6596(7) 0.7011(4) 0.0683(11) Uani d 1
H H13 0.1113 0.7876 0.7645 0.082 Uiso calc 1
C C10 0.11003(19) 0.2786(8) 0.5152(5) 0.0696(11) Uani d 1
H H10 0.1096 0.1490 0.4532 0.083 Uiso calc 1
C C11 0.0610(2) 0.3429(9) 0.5812(5) 0.0816(13) Uani d 1
H H11 0.0275 0.2566 0.5635 0.098 Uiso calc 1
C C3 0.39140(18) 0.9208(7) 0.9065(5) 0.0704(11) Uani d 1
H H3 0.4214 0.8717 0.9694 0.084 Uiso calc 1
C C12 0.06136(19) 0.5340(10) 0.6729(5) 0.0851(14) Uani d 1
H H12 0.0280 0.5786 0.7160 0.102 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
O1 C7 N1 122.0(3)
O1 C7 C1 120.9(3)
N1 C7 C1 117.2(3)
O2 C9 C10 123.4(3)
O2 C9 C8 116.7(3)
C10 C9 C8 119.9(4)
C9 O2 HO2 109.5
C7 N1 C8 122.9(3)
C7 N1 H1 118.6
C8 N1 H1 118.6
C2 C1 C6 119.2(3)
C2 C1 C7 119.0(3)
C6 C1 C7 121.7(3)
C5 C6 C1 119.9(4)
C5 C6 H6 120.1
C1 C6 H6 120.1
C9 C8 C13 119.4(4)
C9 C8 N1 119.0(3)
C13 C8 N1 121.5(3)
C4 C5 C6 119.6(4)
C4 C5 H5 120.2
C6 C5 H5 120.2
C1 C2 C3 121.1(4)
C1 C2 H2 119.4
C3 C2 H2 119.4
C5 C4 C3 121.6(4)
C5 C4 Br1 118.7(3)
C3 C4 Br1 119.7(3)
C12 C13 C8 120.3(4)
C12 C13 H13 119.9
C8 C13 H13 119.9
C11 C10 C9 120.1(4)
C11 C10 H10 120.0
C9 C10 H10 120.0
C12 C11 C10 120.2(4)
C12 C11 H11 119.9
C10 C11 H11 119.9
C4 C3 C2 118.6(4)
C4 C3 H3 120.7
C2 C3 H3 120.7
C11 C12 C13 120.1(4)
C11 C12 H12 120.0
C13 C12 H12 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.895(4)
O1 C7 1.239(4)
C7 N1 1.334(4)
C7 C1 1.497(5)
C9 O2 1.357(4)
C9 C10 1.380(5)
C9 C8 1.384(5)
O2 HO2 0.8200
N1 C8 1.423(5)
N1 H1 0.8600
C1 C2 1.377(5)
C1 C6 1.388(5)
C6 C5 1.387(6)
C6 H6 0.9300
C8 C13 1.384(5)
C5 C4 1.365(7)
C5 H5 0.9300
C2 C3 1.383(6)
C2 H2 0.9300
C4 C3 1.374(6)
C13 C12 1.375(7)
C13 H13 0.9300
C10 C11 1.378(7)
C10 H10 0.9300
C11 C12 1.372(7)
C11 H11 0.9300
C3 H3 0.9300
C12 H12 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 HO2 O1 4_565 0.82 2.00 2.682(3) 141
N1 H1 O1 4_575 0.86 2.02 2.824(3) 155
C6 H6 O2 1_565 0.93 2.56 3.458(5) 164
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
O1 C7 N1 C8 0.8(5)
C1 C7 N1 C8 -179.6(3)
O1 C7 C1 C2 24.5(5)
N1 C7 C1 C2 -155.1(3)
O1 C7 C1 C6 -153.9(3)
N1 C7 C1 C6 26.5(4)
C2 C1 C6 C5 0.3(5)
C7 C1 C6 C5 178.7(3)
O2 C9 C8 C13 177.9(3)
C10 C9 C8 C13 -1.4(5)
O2 C9 C8 N1 -0.7(4)
C10 C9 C8 N1 180.0(3)
C7 N1 C8 C9 -107.5(4)
C7 N1 C8 C13 73.9(5)
C1 C6 C5 C4 -0.5(6)
C6 C1 C2 C3 -0.3(5)
C7 C1 C2 C3 -178.8(3)
C6 C5 C4 C3 0.7(6)
C6 C5 C4 Br1 -178.2(3)
C9 C8 C13 C12 0.3(6)
N1 C8 C13 C12 178.8(4)
O2 C9 C10 C11 -178.0(4)
C8 C9 C10 C11 1.3(6)
C9 C10 C11 C12 -0.1(7)
C5 C4 C3 C2 -0.8(6)
Br1 C4 C3 C2 178.1(3)
C1 C2 C3 C4 0.6(6)
C10 C11 C12 C13 -1.1(7)
C8 C13 C12 C11 1.0(7)
