#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/40/2204084.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_2204084
loop_
_publ_author_name
'Liu, Zhao-Di'
'Qu, Yang'
'Tan, Min-Yu'
'Zhu, Hai-Liang'
_publ_section_title
;
 5-Bromosalicylic acid
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1310
_journal_page_last               o1311
_journal_paper_doi               10.1107/S1600536804016411
_journal_volume                  60
_journal_year                    2004
_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        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.06(3)
_cell_angle_beta                 90.40(3)
_cell_angle_gamma                101.19(3)
_cell_formula_units_Z            4
_cell_length_a                   4.8050(10)
_cell_length_b                   12.047(2)
_cell_length_c                   14.666(3)
_cell_measurement_reflns_used    2884
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      6
_cell_volume                     756.9(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5095
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.380
_exptl_absorpt_correction_T_max  0.767
_exptl_absorpt_correction_T_min  0.514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0474P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                1786
_reflns_number_total             2884
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6123.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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               2204084
_cod_database_fobs_code          2204084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
Br1 0.25119(15) 0.48915(6) 1.17770(5) 0.0856(3) Uani d . 1 Br
Br2 1.18701(11) 0.81837(5) 0.36237(4) 0.0617(2) Uani d . 1 Br
C1 0.5842(9) 0.1934(5) 0.9862(4) 0.0453(12) Uani d . 1 C
C2 0.4840(10) 0.1796(5) 0.8913(4) 0.0517(13) Uani d . 1 C
C3 0.3207(11) 0.2593(5) 0.8842(4) 0.0569(14) Uani d . 1 C
H3A 0.2526 0.2495 0.8191 0.080 Uiso d R 1 H
C4 0.2555(12) 0.3509(5) 0.9682(5) 0.0631(15) Uani d . 1 C
H4A 0.1427 0.4059 0.9627 0.080 Uiso d R 1 H
C5 0.3520(11) 0.3630(5) 1.0618(4) 0.0539(13) Uani d . 1 C
C6 0.5135(10) 0.2875(5) 1.0717(4) 0.0520(13) Uani d . 1 C
H6A 0.5801 0.2982 1.1372 0.080 Uiso d R 1 H
C7 0.7631(10) 0.1111(5) 0.9956(4) 0.0527(13) Uani d . 1 C
C8 0.6147(9) 0.7144(4) 0.5390(4) 0.0425(12) Uani d . 1 C
C9 0.7277(11) 0.7988(5) 0.6366(4) 0.0478(12) Uani d . 1 C
C10 0.9752(11) 0.8867(5) 0.6504(4) 0.0543(14) Uani d . 1 C
H10A 1.0527 0.9449 0.7171 0.080 Uiso d R 1 H
C11 1.1106(11) 0.8911(5) 0.5699(4) 0.0523(13) Uani d . 1 C
H11A 1.2839 0.9517 0.5800 0.080 Uiso d R 1 H
C12 0.9997(10) 0.8090(5) 0.4732(4) 0.0458(12) Uani d . 1 C
C13 0.7562(10) 0.7204(4) 0.4573(4) 0.0429(12) Uani d . 1 C
H13A 0.6814 0.6627 0.3901 0.080 Uiso d R 1 H
C14 0.3498(10) 0.6208(4) 0.5223(4) 0.0415(11) Uani d . 1 C
O1 0.8472(8) 0.1329(3) 1.0875(3) 0.0646(10) Uani d . 1 O
H1A 0.9495 0.0820 1.0857 0.080 Uiso d R 1 H
O2 0.8317(8) 0.0295(4) 0.9219(3) 0.0626(10) Uani d . 1 O
O3 0.5389(8) 0.0905(4) 0.8053(3) 0.0647(10) Uani d . 1 O
H3B 0.6431 0.0485 0.8187 0.080 Uiso d R 1 H
O4 0.2719(7) 0.5438(3) 0.4282(2) 0.0548(9) Uani d . 1 O
H4B 0.1153 0.4942 0.4244 0.080 Uiso d R 1 H
O5 0.2157(7) 0.6147(3) 0.5919(3) 0.0535(9) Uani d . 1 O
O6 0.6054(8) 0.8009(3) 0.7193(3) 0.0674(11) Uani d . 1 O
H6C 0.4536 0.7446 0.7026 0.080 Uiso d R 1 H
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
C6 C1 C2 118.7(5)
C6 C1 C7 120.9(5)
C2 C1 C7 120.5(5)
O3 C2 C3 118.0(5)
O3 C2 C1 122.5(5)
C3 C2 C1 119.5(5)
C4 C3 C2 121.0(5)
C4 C3 H3A 119.8
C2 C3 H3A 119.2
C3 C4 C5 119.2(5)
C3 C4 H4A 120.5
C5 C4 H4A 120.2
C6 C5 C4 121.4(5)
C6 C5 Br1 120.2(4)
C4 C5 Br1 118.4(4)
C5 C6 C1 120.1(5)
C5 C6 H6A 120.0
C1 C6 H6A 119.8
O2 C7 O1 122.6(5)
O2 C7 C1 122.0(5)
O1 C7 C1 115.3(5)
C9 C8 C13 119.3(5)
C9 C8 C14 120.4(5)
C13 C8 C14 120.3(4)
O6 C9 C10 117.1(4)
O6 C9 C8 123.5(5)
C10 C9 C8 119.4(5)
C11 C10 C9 120.5(5)
C11 C10 H10A 119.8
C9 C10 H10A 119.7
C10 C11 C12 120.5(5)
C10 C11 H11A 120.1
C12 C11 H11A 119.3
C13 C12 C11 120.3(5)
C13 C12 Br2 119.8(4)
C11 C12 Br2 119.9(4)
C12 C13 C8 119.9(4)
C12 C13 H13A 120.0
C8 C13 H13A 120.0
O5 C14 O4 123.0(4)
O5 C14 C8 122.2(5)
O4 C14 C8 114.8(4)
C7 O1 H1A 108.8
C2 O3 H3B 109.7
C14 O4 H4B 109.4
C9 O6 H6C 109.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.904(5)
Br2 C12 1.897(5)
C1 C6 1.403(7)
C1 C2 1.404(7)
C1 C7 1.476(7)
C2 O3 1.350(6)
C2 C3 1.386(7)
C3 C4 1.366(7)
C3 H3A 0.9601
C4 C5 1.387(7)
C4 H4A 0.9602
C5 C6 1.353(7)
C6 H6A 0.9601
C7 O2 1.227(6)
C7 O1 1.309(6)
C8 C9 1.402(6)
C8 C13 1.403(6)
C8 C14 1.471(6)
C9 O6 1.345(6)
C9 C10 1.381(7)
C10 C11 1.367(7)
C10 H10A 0.9600
C11 C12 1.384(7)
C11 H11A 0.9600
C12 C13 1.368(7)
C13 H13A 0.9600
C14 O5 1.231(5)
C14 O4 1.312(5)
O1 H1A 0.8499
O3 H3B 0.8500
O4 H4B 0.8500
O6 H6C 0.8500
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 H1A O2 2_757 0.85 1.83 2.681(5) 179
O3 H3B O2 . 0.85 1.87 2.614(5) 145
O4 H4B O5 2_566 0.85 1.80 2.648(5) 177
O6 H6C O5 . 0.85 1.90 2.633(5) 144
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
C6 C1 C2 O3 -179.1(4)
C7 C1 C2 O3 1.6(7)
C6 C1 C2 C3 0.5(7)
C7 C1 C2 C3 -178.8(4)
O3 C2 C3 C4 179.5(5)
C1 C2 C3 C4 -0.1(8)
C2 C3 C4 C5 -0.7(8)
C3 C4 C5 C6 1.2(8)
C3 C4 C5 Br1 -178.7(4)
C4 C5 C6 C1 -0.8(8)
Br1 C5 C6 C1 179.1(3)
C2 C1 C6 C5 -0.1(7)
C7 C1 C6 C5 179.3(4)
C6 C1 C7 O2 -178.8(5)
C2 C1 C7 O2 0.5(7)
C6 C1 C7 O1 0.0(7)
C2 C1 C7 O1 179.3(4)
C13 C8 C9 O6 179.3(4)
C14 C8 C9 O6 -0.4(7)
C13 C8 C9 C10 0.3(7)
C14 C8 C9 C10 -179.4(4)
O6 C9 C10 C11 -179.4(5)
C8 C9 C10 C11 -0.4(8)
C9 C10 C11 C12 1.0(8)
C10 C11 C12 C13 -1.5(8)
C10 C11 C12 Br2 178.9(4)
C11 C12 C13 C8 1.4(7)
Br2 C12 C13 C8 -179.0(3)
C9 C8 C13 C12 -0.8(7)
C14 C8 C13 C12 178.9(4)
C9 C8 C14 O5 1.6(7)
C13 C8 C14 O5 -178.1(4)
C9 C8 C14 O4 -177.2(4)
C13 C8 C14 O4 3.1(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6706
