#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/06/2240653.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_2240653
loop_
_publ_author_name
'Laus, Gerhard'
'Kahlenberg, Volker'
'Gelbrich, Thomas'
'Nerdinger, Sven'
'Schottenberger, Herwig'
_publ_section_title
;
 Crystal structure of 3-bromo-2-hydroxybenzoic acid
;
_journal_coeditor_code           WM5143
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              531
_journal_page_last               535
_journal_paper_doi               10.1107/S2056989015007331
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C7 H5 Br O3'
_chemical_formula_moiety         'C7 H5 Br O3'
_chemical_formula_sum            'C7 H5 Br O3'
_chemical_formula_weight         217.02
_chemical_name_systematic
;
3-Bromo-2-hydroxybenzoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90.208(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.7978(4)
_cell_length_b                   10.5567(6)
_cell_length_c                   18.0366(10)
_cell_measurement_reflns_used    1701
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.093
_cell_measurement_theta_min      2.977
_cell_volume                     723.12(10)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al.,
2006) and
XP (Sheldrick, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.3575
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Xcalibur (Ruby, Gemini ultra)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4627
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.070
_diffrn_reflns_theta_min         2.971
_exptl_absorpt_coefficient_mu    5.632
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.09355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.993
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.791
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1594
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0507P)²+0.2934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                1309
_reflns_number_total             1594
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm5143sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2240653
_cod_database_fobs_code          2240653
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.266
_shelx_estimated_absorpt_t_max   0.661
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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'
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 0.28846(10) 0.31635(3) 0.19518(2) 0.02717(17) Uani d 1
O O2 0.9783(9) 0.1747(2) 0.51138(16) 0.0323(7) Uani d 1
H H2 1.055(16) 0.109(4) 0.535(3) 0.08(2) Uiso d 1
O O1 0.5137(8) 0.1225(2) 0.30358(15) 0.0304(7) Uani d 1
H H1 0.574(15) 0.064(4) 0.334(3) 0.060(16) Uiso d 1
O O3 0.7802(8) 0.0380(2) 0.42729(15) 0.0330(7) Uani d 1
C C3 0.4674(10) 0.3437(3) 0.2917(2) 0.0214(8) Uani d 1
C C2 0.5652(10) 0.2381(3) 0.3340(2) 0.0216(8) Uani d 1
C C1 0.7081(10) 0.2576(3) 0.4042(2) 0.0214(8) Uani d 1
C C7 0.8233(10) 0.1476(4) 0.4484(2) 0.0241(8) Uani d 1
C C4 0.5058(10) 0.4649(3) 0.3191(2) 0.0251(8) Uani d 1
H H4 0.4369 0.5356 0.2899 0.030 Uiso calc 1
C C6 0.7467(10) 0.3806(3) 0.4318(2) 0.0242(8) Uani d 1
H H6 0.8432 0.3935 0.4799 0.029 Uiso calc 1
C C5 0.6454(11) 0.4832(4) 0.3896(2) 0.0284(9) Uani d 1
H H5 0.6711 0.5666 0.4087 0.034 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 0.0033 0.0016 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O2 H2 114(4)
C2 O1 H1 111(4)
C4 C3 C2 121.0(4)
C4 C3 Br1 120.7(3)
C2 C3 Br1 118.3(3)
O1 C2 C1 123.9(3)
O1 C2 C3 117.4(3)
C1 C2 C3 118.7(3)
C2 C1 C6 120.1(3)
C2 C1 C7 119.3(3)
C6 C1 C7 120.6(3)
O3 C7 O2 122.2(3)
O3 C7 C1 122.4(3)
O2 C7 C1 115.4(3)
C3 C4 C5 119.8(3)
C3 C4 H4 120.1
C5 C4 H4 120.1
C5 C6 C1 120.3(4)
C5 C6 H6 119.9
C1 C6 H6 119.9
C6 C5 C4 120.1(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.889(4)
O2 C7 1.309(5)
O2 H2 0.87(2)
O1 C2 1.352(5)
O1 H1 0.85(2)
O3 C7 1.229(5)
C3 C4 1.379(5)
C3 C2 1.400(5)
C2 C1 1.391(5)
C1 C6 1.398(6)
C1 C7 1.474(5)
C4 C5 1.388(6)
C4 H4 0.9500
C6 C5 1.379(5)
C6 H6 0.9500
C5 H5 0.9500
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
O1 H1 O3 . 0.85(2) 1.88(4) 2.604(4) 142(5)
O2 H2 O3 3_756 0.87(2) 1.80(2) 2.664(4) 172(6)
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
C4 C3 C2 O1 178.9(4)
Br1 C3 C2 O1 -2.2(5)
C4 C3 C2 C1 -1.0(6)
Br1 C3 C2 C1 177.9(3)
O1 C2 C1 C6 -178.9(3)
C3 C2 C1 C6 1.0(5)
O1 C2 C1 C7 2.1(6)
C3 C2 C1 C7 -178.0(3)
C2 C1 C7 O3 -4.2(6)
C6 C1 C7 O3 176.9(4)
C2 C1 C7 O2 175.1(3)
C6 C1 C7 O2 -3.8(5)
C2 C3 C4 C5 0.4(6)
Br1 C3 C4 C5 -178.5(3)
C2 C1 C6 C5 -0.3(6)
C7 C1 C6 C5 178.6(4)
C1 C6 C5 C4 -0.3(6)
C3 C4 C5 C6 0.3(6)
