#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/50/2205076.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_2205076
loop_
_publ_author_name
'Bhuvanesh, Nattamai S. P.'
'Reibenspies, Joseph H.'
_publ_section_title
;
 4-Bromophenylboronic acid ethanol 0.04-solvate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o362
_journal_page_last               o364
_journal_paper_doi               10.1107/S1600536804033744
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H6 B Br O2, 0.04 C2 H6 O1'
_chemical_formula_moiety         'C6 H6 B Br O2, 0.04 C2 H6 O1'
_chemical_formula_sum            'C6.08 H6.24 B Br O2.04'
_chemical_formula_weight         202.67
_chemical_name_common            'p-bromophenylboronic acid'
_chemical_name_systematic
;
 4-bromophenylboronic acid'
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.902(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   29.1857(11)
_cell_length_b                   9.8249(4)
_cell_length_c                   12.0285(5)
_cell_measurement_reflns_used    5323
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      58.54
_cell_measurement_theta_min      3.10
_cell_volume                     3375.0(2)
_computing_cell_refinement
'CELL-NOW (Sheldrick, 2003) and SAINT (Bruker--Nonius, 2003)'
_computing_data_collection       'FRAMBO (Bruker--Nonius, 2003)'
_computing_data_reduction
;
SAINT
;
_computing_molecular_graphics
'X-seed (Barbour, 1999) and Diamond (Brandenbourg, 2001)'
_computing_publication_material
;SHELXTL (Sheldrick, 2001) and Platon (Spek, 2004)  as incorporated
in WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2001)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15334
_diffrn_reflns_theta_full        58.93
_diffrn_reflns_theta_max         58.93
_diffrn_reflns_theta_min         6.20
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.169
_exptl_absorpt_correction_T_max  0.7905
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1585
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.951
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0495
_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)+(0.0951P)²+7.7358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1487
_reflns_number_gt                1953
_reflns_number_total             2529
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6113.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2205076
_cod_database_fobs_code          2205076
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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 0.10930(3) 0.0000 1.15897(6) 0.0553(3) Uani d S 1 Br
Br2 0.18168(3) 0.0000 0.43533(7) 0.0561(3) Uani d S 1 Br
Br3 0.26821(3) 0.0000 0.74754(10) 0.0767(4) Uani d S 1 Br
Br4 0.24421(4) 0.0000 1.11904(9) 0.1026(5) Uani d S 1 Br
B1 0.3895(3) 0.0000 0.3777(7) 0.0364(18) Uani d S 1 B
B2 0.4722(3) 0.0000 0.6587(6) 0.0332(18) Uani d S 1 B
B3 -0.0174(3) 0.0000 0.6723(6) 0.0327(17) Uani d S 1 B
B4 0.1077(3) 0.0000 0.6452(6) 0.0316(17) Uani d S 1 B
C1 0.3372(2) 0.0000 0.3902(5) 0.0319(15) Uani d S 1 C
C2 0.31330(17) 0.1214(5) 0.3959(4) 0.0417(12) Uani d . 1 C
H2 0.3289 0.2054 0.3913 0.050 Uiso calc R 1 H
C3 0.26742(17) 0.1220(6) 0.4080(4) 0.0432(13) Uani d . 1 C
H3 0.2515 0.2057 0.4114 0.052 Uiso calc R 1 H
C4 0.2448(2) 0.0000 0.4151(6) 0.0413(17) Uani d S 1 C
C5 0.4204(2) 0.0000 0.6800(5) 0.0325(15) Uani d S 1 C
C6 0.39688(18) 0.1209(5) 0.6913(5) 0.0476(13) Uani d . 1 C
H6 0.4121 0.2050 0.6841 0.057 Uiso calc R 1 H
C7 0.35231(19) 0.1223(6) 0.7125(5) 0.0554(15) Uani d . 1 C
H7 0.3372 0.2062 0.7214 0.066 Uiso calc R 1 H
C8 0.3297(3) 0.0000 0.7209(7) 0.050(2) Uani d S 1 C
C9 0.0142(2) 0.0000 0.7927(5) 0.0309(15) Uani d S 1 C
C10 0.0292(2) 0.1183(6) 0.8500(5) 0.0595(17) Uani d . 1 C
H10 0.0203 0.2027 0.8134 0.071 Uiso calc R 1 H
C11 0.0569(3) 0.1196(6) 0.9599(5) 0.0683(19) Uani d . 1 C
H11 0.0661 0.2033 0.9974 0.082 Uiso calc R 1 H
C12 0.0705(3) 0.0000 1.0117(6) 0.0451(18) Uani d S 1 C
C13 0.1415(2) 0.0000 0.7645(6) 0.0329(15) Uani d S 1 C
C14 0.15724(19) 0.1206(6) 0.8203(4) 0.0486(14) Uani d . 1 C
H14 0.1473 0.2050 0.7848 0.058 Uiso calc R 1 H
C15 0.1872(2) 0.1208(7) 0.9267(5) 0.0608(17) Uani d . 1 C
H15 0.1973 0.2043 0.9637 0.073 Uiso calc R 1 H
C16 0.2020(3) 0.0000 0.9772(6) 0.057(2) Uani d S 1 C
O1 -0.03255(12) -0.1186(3) 0.6166(3) 0.0396(8) Uani d . 1 O
H1 -0.0431 -0.1020 0.5476 0.059 Uiso calc R 1 H
O2 0.49501(12) 0.1180(3) 0.6497(3) 0.0419(8) Uani d . 1 O
H2A 0.4984 0.1279 0.5824 0.063 Uiso calc R 1 H
O3 0.41357(12) 0.1171(3) 0.3713(3) 0.0470(9) Uani d . 1 O
H3A 0.4238 0.1176 0.3109 0.071 Uiso calc R 1 H
O4 0.09238(12) 0.1174(3) 0.5902(3) 0.0415(8) Uani d . 1 O
H4 0.0930 0.1097 0.5210 0.062 Uiso calc R 1 H
O20 0.0713(9) 0.5000 1.0222(18) 0.022(4) Uani d SP 0.16 O
H20A 0.0420 0.5000 0.9954 0.033 Uiso d SPR 0.16 H
C21 0.1441(13) 0.5000 0.941(3) 0.022(4) Uani d SP 0.16 C
H21A 0.1480 0.5000 0.8641 0.033 Uiso d SPR 0.16 H
H21B 0.1586 0.5798 0.9794 0.033 Uiso d PR 0.16 H
C22 0.0908(14) 0.5000 0.944(3) 0.022(4) Uani d SP 0.16 C
H22A 0.0787 0.5778 0.8993 0.026 Uiso d PR 0.16 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O3 B1 O3 6 . 115.7(7)
O3 B1 C1 6 . 122.1(3)
O3 B1 C1 . . 122.1(3)
O2 B2 O2 . 6 118.0(6)
O2 B2 C5 . . 121.0(3)
O2 B2 C5 6 . 121.0(3)
O1 B3 O1 . 6 116.4(6)
O1 B3 C9 . . 121.8(3)
O1 B3 C9 6 . 121.8(3)
O4 B4 O4 6 . 116.3(6)
O4 B4 C13 6 . 121.9(3)
O4 B4 C13 . . 121.9(3)
C2 C1 C2 6 . 118.2(6)
C2 C1 B1 6 . 120.9(3)
C2 C1 B1 . . 120.9(3)
C3 C2 C1 . . 121.1(5)
C3 C2 H2 . . 119.4
C1 C2 H2 . . 119.4
C2 C3 C4 . . 119.4(5)
C2 C3 H3 . . 120.3
C4 C3 H3 . . 120.3
C3 C4 C3 . 6 120.7(6)
C3 C4 Br2 . . 119.7(3)
C3 C4 Br2 6 . 119.7(3)
C6 C5 C6 6 . 117.1(6)
C6 C5 B2 6 . 121.4(3)
C6 C5 B2 . . 121.4(3)
C7 C6 C5 . . 122.0(5)
C7 C6 H6 . . 119.0
C5 C6 H6 . . 119.0
C6 C7 C8 . . 119.1(5)
C6 C7 H7 . . 120.4
C8 C7 H7 . . 120.4
C7 C8 C7 . 6 120.5(7)
C7 C8 Br3 . . 119.7(3)
C7 C8 Br3 6 . 119.7(3)
C10 C9 C10 . 6 115.4(7)
C10 C9 B3 . . 122.3(3)
C10 C9 B3 6 . 122.3(3)
C9 C10 C11 . . 122.8(5)
C9 C10 H10 . . 118.6
C11 C10 H10 . . 118.6
C12 C11 C10 . . 119.0(6)
C12 C11 H11 . . 120.5
C10 C11 H11 . . 120.5
C11 C12 C11 6 . 120.9(7)
C11 C12 Br1 6 . 119.5(4)
C11 C12 Br1 . . 119.5(4)
C14 C13 C14 . 6 116.7(7)
C14 C13 B4 . . 121.7(3)
C14 C13 B4 6 . 121.7(3)
C13 C14 C15 . . 121.7(6)
C13 C14 H14 . . 119.1
C15 C14 H14 . . 119.1
C16 C15 C14 . . 119.3(6)
C16 C15 H15 . . 120.4
C14 C15 H15 . . 120.4
C15 C16 C15 6 . 121.3(8)
C15 C16 Br4 6 . 119.4(4)
C15 C16 Br4 . . 119.4(4)
B3 O1 H1 . . 109.5
B2 O2 H2A . . 109.5
B1 O3 H3A . . 109.5
B4 O4 H4 . . 109.5
C22 O20 H20A . . 108.0
C22 C21 H21A . . 109.7
C22 C21 H21B . . 109.3
H21A C21 H21B . . 109.5
O20 C22 C21 . . 131(3)
O20 C22 H22A . . 105.0
C21 C22 H22A . . 104.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C12 . 1.896(7)
Br2 C4 . 1.908(7)
Br3 C8 . 1.888(7)
Br4 C16 . 1.887(8)
B1 O3 6 1.359(6)
B1 O3 . 1.359(6)
B1 C1 . 1.565(10)
B2 O2 . 1.353(5)
B2 O2 6 1.353(5)
B2 C5 . 1.585(10)
B3 O1 . 1.371(5)
B3 O1 6 1.371(5)
B3 C9 . 1.549(10)
B4 O4 6 1.358(5)
B4 O4 . 1.358(5)
B4 C13 . 1.565(10)
C1 C2 6 1.390(6)
C1 C2 . 1.390(6)
C2 C3 . 1.377(7)
C2 H2 . 0.9500
C3 C4 . 1.379(6)
C3 H3 . 0.9500
C4 C3 6 1.379(6)
C5 C6 6 1.392(6)
C5 C6 . 1.392(6)
C6 C7 . 1.376(7)
C6 H6 . 0.9500
C7 C8 . 1.384(7)
C7 H7 . 0.9500
C8 C7 6 1.384(7)
C9 C10 . 1.375(7)
C9 C10 6 1.375(7)
C10 C11 . 1.401(8)
C10 H10 . 0.9500
C11 C12 . 1.350(7)
C11 H11 . 0.9500
C12 C11 6 1.350(7)
C13 C14 . 1.392(7)
C13 C14 6 1.392(7)
C14 C15 . 1.395(8)
C14 H14 . 0.9500
C15 C16 . 1.361(8)
C15 H15 . 0.9500
C16 C15 6 1.361(8)
O1 H1 . 0.8400
O2 H2A . 0.8400
O3 H3A . 0.8400
O4 H4 . 0.8400
O20 C22 . 1.20(4)
O20 H20A . 0.8499
C21 C22 . 1.56(5)
C21 H21A . 0.9600
C21 H21B . 0.9600
C22 H22A . 0.9600
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O3 B1 C1 C2 6 6 0.3(10)
O3 B1 C1 C2 . 6 179.7(6)
O3 B1 C1 C2 6 . -179.7(6)
O3 B1 C1 C2 . . -0.3(10)
C2 C1 C2 C3 6 . 0.7(10)
B1 C1 C2 C3 . . -179.4(5)
C1 C2 C3 C4 . . 0.3(8)
C2 C3 C4 C3 . 6 -1.2(10)
C2 C3 C4 Br2 . . 178.6(4)
O2 B2 C5 C6 . 6 -178.9(6)
O2 B2 C5 C6 6 6 0.7(10)
O2 B2 C5 C6 . . -0.7(10)
O2 B2 C5 C6 6 . 178.9(6)
C6 C5 C6 C7 6 . -0.1(11)
B2 C5 C6 C7 . . -178.4(6)
C5 C6 C7 C8 . . -1.2(10)
C6 C7 C8 C7 . 6 2.6(12)
C6 C7 C8 Br3 . . -179.0(5)
O1 B3 C9 C10 . . -179.2(6)
O1 B3 C9 C10 6 . -0.5(10)
O1 B3 C9 C10 . 6 0.5(10)
O1 B3 C9 C10 6 6 179.2(6)
C10 C9 C10 C11 6 . -1.1(12)
B3 C9 C10 C11 . . 178.6(6)
C9 C10 C11 C12 . . 1.2(11)
C10 C11 C12 C11 . 6 -1.2(13)
C10 C11 C12 Br1 . . 178.5(5)
O4 B4 C13 C14 6 . 179.7(5)
O4 B4 C13 C14 . . 0.4(9)
O4 B4 C13 C14 6 6 -0.4(9)
O4 B4 C13 C14 . 6 -179.7(5)
C14 C13 C14 C15 6 . -0.2(10)
B4 C13 C14 C15 . . 179.8(5)
C13 C14 C15 C16 . . 0.7(9)
C14 C15 C16 C15 . 6 -1.3(12)
C14 C15 C16 Br4 . . 177.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139067411
