#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/58/4125815.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4125815
loop_
_publ_author_name
'Georgiou, Irene'
'Kervyn, Simon'
'Rossignon, Alexandre'
'De Leo, Federica'
'Wouters, Johan'
'Bruylants, Gilles'
'Bonifazi, Davide'
_publ_section_title
;
 Versatile Self-Adapting Boronic Acids for H-Bond Recognition: From
 Discrete to Polymeric Supramolecules.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2710
_journal_page_last               2727
_journal_paper_doi               10.1021/jacs.6b11362
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C6 H5 B Br2 O2, C8 H6 N2'
_chemical_formula_sum            'C14 H11 B Br2 N2 O2'
_chemical_formula_weight         409.88
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.118(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5305(11)
_cell_length_b                   14.1551(11)
_cell_length_c                   8.1397(6)
_cell_measurement_reflns_used    2407
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1520
_cell_measurement_theta_min      2.8600
_cell_volume                     1552.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7705
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    5.224
_exptl_absorpt_correction_T_max  0.5500
_exptl_absorpt_correction_T_min  0.2697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0396
_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)+(0.0313P)²+0.7113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                1829
_reflns_number_total             2738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b11362_si_007.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4125815
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3390(3) 0.0201(3) 0.0331(4) 0.0494(10) Uani 1 1 d .
C2 C 0.3839(3) 0.0905(3) 0.1329(4) 0.0551(11) Uani 1 1 d .
C3 C 0.4587(3) 0.0727(4) 0.2555(5) 0.0699(14) Uani 1 1 d .
H3 H 0.4861 0.1221 0.3199 0.084 Uiso 1 1 calc R
C4 C 0.4922(3) -0.0171(5) 0.2821(5) 0.0758(16) Uani 1 1 d .
H4 H 0.5431 -0.0290 0.3639 0.091 Uiso 1 1 calc R
C5 C 0.4510(3) -0.0903(4) 0.1881(5) 0.0693(13) Uani 1 1 d .
H5 H 0.4732 -0.1520 0.2054 0.083 Uiso 1 1 calc R
C6 C 0.3757(3) -0.0698(3) 0.0673(5) 0.0559(11) Uani 1 1 d .
B1 B 0.2516(3) 0.0423(3) -0.1047(5) 0.0489(11) Uani 1 1 d .
O1 O 0.2747(2) 0.0621(2) -0.2586(3) 0.0654(9) Uani 1 1 d .
O2 O 0.1593(2) 0.0407(3) -0.0579(4) 0.0698(10) Uani 1 1 d .
Br1 Br 0.34322(4) 0.21804(4) 0.09733(6) 0.0784(2) Uani 1 1 d .
Br2 Br 0.32148(4) -0.17406(4) -0.05835(7) 0.0883(2) Uani 1 1 d .
H2O H 0.116(3) 0.055(3) -0.128(5) 0.068(15) Uiso 1 1 d .
H1O H 0.227(4) 0.071(4) -0.326(6) 0.10(2) Uiso 1 1 d .
C7 C 0.0882(3) 0.9130(3) 0.2513(5) 0.0619(12) Uani 1 1 d .
H7 H 0.0985 0.9295 0.1436 0.074 Uiso 1 1 calc R
C8 C 0.1712(3) 0.8932(3) 0.3597(6) 0.0672(12) Uani 1 1 d .
H8 H 0.2346 0.8965 0.3245 0.081 Uiso 1 1 calc R
C9 C 0.1579(3) 0.8693(3) 0.5165(6) 0.0645(12) Uani 1 1 d .
H9 H 0.2124 0.8570 0.5913 0.077 Uiso 1 1 calc R
C10 C 0.0614(3) 0.8630(3) 0.5663(5) 0.0478(10) Uani 1 1 d .
C11 C 0.0383(4) 0.8380(3) 0.7270(5) 0.0611(12) Uani 1 1 d .
H11 H 0.0885 0.8236 0.8088 0.073 Uiso 1 1 calc R
C12 C -0.0582(4) 0.8353(3) 0.7594(5) 0.0649(12) Uani 1 1 d .
H12 H -0.0753 0.8189 0.8637 0.078 Uiso 1 1 calc R
C13 C -0.1310(3) 0.8577(3) 0.6342(5) 0.0613(12) Uani 1 1 d .
H13 H -0.1967 0.8557 0.6591 0.074 Uiso 1 1 calc R
C14 C -0.0176(3) 0.8840(2) 0.4483(4) 0.0435(9) Uani 1 1 d .
N1 N -0.1139(2) 0.8813(2) 0.4832(4) 0.0531(8) Uani 1 1 d .
N2 N -0.0037(2) 0.9098(2) 0.2911(4) 0.0511(8) Uani 1 1 d .
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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 114.2(3)
C6 C1 B1 123.7(4)
C2 C1 B1 122.1(4)
C3 C2 C1 123.2(4)
C3 C2 Br1 117.8(4)
C1 C2 Br1 119.0(3)
C4 C3 C2 119.8(5)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.2(4)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 118.3(5)
C4 C5 H5 120.9
C6 C5 H5 120.9
C5 C6 C1 124.4(4)
C5 C6 Br2 116.3(4)
C1 C6 Br2 119.3(3)
O2 B1 O1 124.7(4)
O2 B1 C1 116.8(4)
O1 B1 C1 118.5(4)
B1 O1 H1O 115(3)
B1 O2 H2O 116(3)
N2 C7 C8 124.3(4)
N2 C7 H7 117.8
C8 C7 H7 117.8
C9 C8 C7 118.8(4)
C9 C8 H8 120.6
C7 C8 H8 120.6
C8 C9 C10 119.7(4)
C8 C9 H9 120.2
C10 C9 H9 120.2
C14 C10 C9 117.4(4)
C14 C10 C11 117.9(4)
C9 C10 C11 124.7(4)
C12 C11 C10 118.8(4)
C12 C11 H11 120.6
C10 C11 H11 120.6
C11 C12 C13 118.9(4)
C11 C12 H12 120.5
C13 C12 H12 120.5
N1 C13 C12 124.9(4)
N1 C13 H13 117.6
C12 C13 H13 117.6
N1 C14 N2 114.8(3)
N1 C14 C10 122.5(3)
N2 C14 C10 122.7(4)
C13 N1 C14 117.0(3)
C7 N2 C14 117.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.385(6)
C1 C2 1.390(6)
C1 B1 1.587(6)
C2 C3 1.379(6)
C2 Br1 1.903(5)
C3 C4 1.361(7)
C3 H3 0.9300
C4 C5 1.376(7)
C4 H4 0.9300
C5 C6 1.382(5)
C5 H5 0.9300
C6 Br2 1.905(4)
B1 O2 1.338(5)
B1 O1 1.347(5)
O1 H1O 0.82(5)
O2 H2O 0.81(4)
C7 N2 1.313(5)
C7 C8 1.394(6)
C7 H7 0.9300
C8 C9 1.348(6)
C8 H8 0.9300
C9 C10 1.405(5)
C9 H9 0.9300
C10 C14 1.403(5)
C10 C11 1.417(5)
C11 C12 1.355(6)
C11 H11 0.9300
C12 C13 1.389(6)
C12 H12 0.9300
C13 N1 1.314(5)
C13 H13 0.9300
C14 N1 1.359(4)
C14 N2 1.360(4)
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 C3 0.0(5)
B1 C1 C2 C3 178.7(4)
C6 C1 C2 Br1 178.7(3)
B1 C1 C2 Br1 -2.6(5)
C1 C2 C3 C4 0.6(6)
Br1 C2 C3 C4 -178.1(3)
C2 C3 C4 C5 -0.7(7)
C3 C4 C5 C6 0.2(6)
C4 C5 C6 C1 0.4(6)
C4 C5 C6 Br2 -179.8(3)
C2 C1 C6 C5 -0.5(6)
B1 C1 C6 C5 -179.2(4)
C2 C1 C6 Br2 179.8(3)
B1 C1 C6 Br2 1.1(5)
C6 C1 B1 O2 90.4(5)
C2 C1 B1 O2 -88.2(5)
C6 C1 B1 O1 -90.3(5)
C2 C1 B1 O1 91.1(5)
N2 C7 C8 C9 -0.1(7)
C7 C8 C9 C10 1.2(7)
C8 C9 C10 C14 -1.1(6)
C8 C9 C10 C11 179.6(4)
C14 C10 C11 C12 0.1(6)
C9 C10 C11 C12 179.4(4)
C10 C11 C12 C13 -0.3(6)
C11 C12 C13 N1 0.3(7)
C9 C10 C14 N1 -179.2(4)
C11 C10 C14 N1 0.2(5)
C9 C10 C14 N2 -0.1(6)
C11 C10 C14 N2 179.2(3)
C12 C13 N1 C14 0.0(6)
N2 C14 N1 C13 -179.3(3)
C10 C14 N1 C13 -0.2(6)
C8 C7 N2 C14 -1.1(6)
N1 C14 N2 C7 -179.7(4)
C10 C14 N2 C7 1.2(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125201
