#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/32/2233248.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_2233248
loop_
_publ_author_name
'Lin, Hong-Yi'
'Fang, Sin-Kai'
'Chen, Kew-Yu'
_publ_section_title
;
 2-(Dibromomethyl)benzoic acid
;
_journal_coeditor_code           LX2208
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o109
_journal_paper_doi               10.1107/S1600536811052858
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H6 Br2 O2'
_chemical_formula_moiety         'C8 H6 Br2 O2'
_chemical_formula_sum            'C8 H6 Br2 O2'
_chemical_formula_weight         293.95
_chemical_name_systematic
;
2-(Dibromomethyl)benzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.709(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9988(6)
_cell_length_b                   25.617(3)
_cell_length_c                   7.1844(8)
_cell_measurement_reflns_used    2762
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      29.2388
_cell_measurement_theta_min      2.8553
_cell_volume                     911.68(18)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_sigmaI/netI    0.0910
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7515
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.30
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    8.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.929
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.1645
_refine_ls_R_factor_gt           0.0908
_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/[σ²(Fo²)+(0.0876P)²+4.8672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2268
_reflns_number_gt                1221
_reflns_number_total             2210
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2208.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2233248
_cod_database_fobs_code          2233248
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Br Br1 0.4317(3) 0.14770(6) 0.73655(16) 0.0676(5) Uani d . 1 2
Br Br2 0.6793(3) 0.22661(4) 0.4627(2) 0.0700(5) Uani d . 1 2
O O1 0.8610(16) 0.0565(3) 0.5279(11) 0.055(2) Uani d . 1 2
O O2 0.7203(17) -0.0025(3) 0.3117(11) 0.057(2) Uani d . 1 2
H H2A 0.8523 -0.0181 0.3649 0.086 Uiso calc R 1 2
C C1 0.613(2) 0.1540(4) 0.5132(14) 0.038(2) Uani d . 1 2
H H1A 0.7859 0.1356 0.5355 0.046 Uiso calc R 1 2
C C2 0.4355(19) 0.1276(3) 0.3520(12) 0.032(2) Uani d . 1 2
C C3 0.216(2) 0.1550(4) 0.2570(14) 0.043(2) Uani d . 1 2
H H3A 0.1840 0.1890 0.2926 0.052 Uiso calc R 1 2
C C4 0.050(2) 0.1329(4) 0.1143(14) 0.045(3) Uani d . 1 2
H H4A -0.0943 0.1519 0.0528 0.054 Uiso calc R 1 2
C C5 0.093(2) 0.0821(4) 0.0596(14) 0.050(3) Uani d . 1 2
H H5A -0.0223 0.0667 -0.0375 0.060 Uiso calc R 1 2
C C6 0.307(2) 0.0547(4) 0.1501(14) 0.041(2) Uani d . 1 2
H H6A 0.3367 0.0207 0.1115 0.049 Uiso calc R 1 2
C C7 0.484(2) 0.0759(4) 0.2988(12) 0.033(2) Uani d . 1 2
C C8 0.702(2) 0.0430(4) 0.3896(14) 0.037(2) Uani d . 1 2
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'
Br Br -0.2901 2.4595 '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 O2 H2A 109.5
C2 C1 Br2 112.5(7)
C2 C1 Br1 107.6(7)
Br2 C1 Br1 110.2(4)
C2 C1 H1A 108.8
Br2 C1 H1A 108.8
Br1 C1 H1A 108.8
C3 C2 C7 119.4(9)
C3 C2 C1 119.2(8)
C7 C2 C1 121.4(8)
C4 C3 C2 121.5(10)
C4 C3 H3A 119.2
C2 C3 H3A 119.2
C3 C4 C5 120.2(10)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C6 C5 C4 119.3(9)
C6 C5 H5A 120.4
C4 C5 H5A 120.4
C5 C6 C7 122.4(9)
C5 C6 H6A 118.8
C7 C6 H6A 118.8
C2 C7 C6 117.3(9)
C2 C7 C8 124.5(9)
C6 C7 C8 118.2(9)
O1 C8 O2 121.5(9)
O1 C8 C7 123.9(9)
O2 C8 C7 114.6(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.951(10)
Br2 C1 1.932(10)
O1 C8 1.235(12)
O2 C8 1.302(11)
O2 H2A 0.8200
C1 C2 1.519(13)
C1 H1A 0.9800
C2 C3 1.399(14)
C2 C7 1.409(12)
C3 C4 1.354(14)
C3 H3A 0.9300
C4 C5 1.386(15)
C4 H4A 0.9300
C5 C6 1.370(15)
C5 H5A 0.9300
C6 C7 1.402(13)
C6 H6A 0.9300
C7 C8 1.461(14)
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 H2A O1 3_756 0.82 1.82 2.641(11) 176
C1 H1A O1 1_555 0.98 2.06 2.784(13) 129
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
Br2 C1 C2 C3 -40.2(11)
Br1 C1 C2 C3 81.4(9)
Br2 C1 C2 C7 141.2(8)
Br1 C1 C2 C7 -97.3(9)
C7 C2 C3 C4 -0.2(15)
C1 C2 C3 C4 -178.9(9)
C2 C3 C4 C5 0.4(16)
C3 C4 C5 C6 -0.7(16)
C4 C5 C6 C7 0.9(17)
C3 C2 C7 C6 0.4(14)
C1 C2 C7 C6 179.1(9)
C3 C2 C7 C8 -178.5(9)
C1 C2 C7 C8 0.1(15)
C5 C6 C7 C2 -0.8(15)
C5 C6 C7 C8 178.3(10)
C2 C7 C8 O1 2.9(16)
C6 C7 C8 O1 -176.1(10)
C2 C7 C8 O2 -176.3(9)
C6 C7 C8 O2 4.7(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 306469
