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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/58/4125822.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_4125822
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         'C14 H8 N4, 2(C9 H13 B O2)'
_chemical_formula_sum            'C32 H34 B2 N4 O4'
_chemical_formula_weight         560.27
_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                109.53(2)
_cell_angle_beta                 105.321(17)
_cell_angle_gamma                104.113(13)
_cell_formula_units_Z            1
_cell_length_a                   7.9753(9)
_cell_length_b                   10.291(2)
_cell_length_c                   10.730(3)
_cell_measurement_reflns_used    2365
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3490
_cell_measurement_theta_min      3.5620
_cell_volume                     745.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Shelxs86
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5051
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.2275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                2143
_reflns_number_total             2638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b11362_si_031.cif
_cod_data_source_block           shelxl
_cod_database_code               4125822
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C10 C 0.5483(2) 0.95216(18) 0.97643(17) 0.0351(4) Uani 1 1 d .
C11 C 0.1938(2) 0.84797(19) 0.95881(18) 0.0396(4) Uani 1 1 d .
C12 C 0.0062(3) 0.7831(2) 0.9452(2) 0.0514(5) Uani 1 1 d .
C13 C -0.0754(3) 0.6353(2) 0.8939(2) 0.0582(6) Uani 1 1 d .
H13 H -0.1970 0.5945 0.8869 0.070 Uiso 1 1 calc R
C14 C 0.2912(3) 0.75099(19) 0.91259(18) 0.0392(4) Uani 1 1 d .
C15 C 0.1969(3) 0.5953(2) 0.8585(2) 0.0520(5) Uani 1 1 d .
H15 H 0.2573 0.5312 0.8286 0.062 Uiso 1 1 calc R
C16 C 0.0212(3) 0.5404(2) 0.8502(2) 0.0590(6) Uani 1 1 d .
H16 H -0.0383 0.4386 0.8152 0.071 Uiso 1 1 calc R
N1 N 0.4648(2) 0.80381(15) 0.91943(15) 0.0398(4) Uani 1 1 d .
N2 N 0.2740(2) 0.99421(16) 1.01250(15) 0.0403(4) Uani 1 1 d .
H12 H -0.061(3) 0.848(2) 0.973(2) 0.062(6) Uiso 1 1 d .
C1 C 0.3985(2) 0.84261(18) 0.61038(17) 0.0362(4) Uani 1 1 d .
C2 C 0.2237(2) 0.84430(19) 0.61188(18) 0.0382(4) Uani 1 1 d .
C3 C 0.2016(3) 0.9786(2) 0.6672(2) 0.0442(5) Uani 1 1 d .
H3 H 0.0857 0.9787 0.6691 0.053 Uiso 1 1 calc R
C4 C 0.3469(3) 1.1127(2) 0.7199(2) 0.0433(5) Uani 1 1 d .
C5 C 0.5170(3) 1.10968(19) 0.71534(19) 0.0416(4) Uani 1 1 d .
H5 H 0.6156 1.1987 0.7491 0.050 Uiso 1 1 calc R
C6 C 0.5454(2) 0.97789(19) 0.66193(18) 0.0372(4) Uani 1 1 d .
C7 C 0.0603(3) 0.7027(2) 0.5551(2) 0.0598(6) Uani 1 1 d .
H7A H -0.0391 0.7241 0.5817 0.090 Uiso 1 1 calc R
H7B H 0.0975 0.6383 0.5943 0.090 Uiso 1 1 calc R
H7C H 0.0180 0.6550 0.4528 0.090 Uiso 1 1 calc R
C8 C 0.3191(4) 1.2579(2) 0.7793(3) 0.0708(7) Uani 1 1 d .
H8A H 0.3495 1.2910 0.8802 0.106 Uiso 1 1 calc R
H8B H 0.1912 1.2442 0.7332 0.106 Uiso 1 1 calc R
H8C H 0.3989 1.3307 0.7622 0.106 Uiso 1 1 calc R
C9 C 0.7350(3) 0.9812(2) 0.6611(2) 0.0546(5) Uani 1 1 d .
H9A H 0.7904 0.9463 0.7281 0.082 Uiso 1 1 calc R
H9B H 0.8134 1.0808 0.6876 0.082 Uiso 1 1 calc R
H9C H 0.7221 0.9184 0.5671 0.082 Uiso 1 1 calc R
B1 B 0.4341(3) 0.6931(2) 0.5573(2) 0.0433(5) Uani 1 1 d .
O1 O 0.4981(2) 0.63586(15) 0.65060(16) 0.0582(4) Uani 1 1 d .
O2 O 0.4037(2) 0.61831(17) 0.41858(15) 0.0642(5) Uani 1 1 d .
H2O H 0.431(4) 0.535(4) 0.400(3) 0.115(10) Uiso 1 1 d .
H1O H 0.511(4) 0.692(3) 0.738(3) 0.086(8) Uiso 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 0.0030 0.0020 '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 0.0010 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 C10 N1 116.86(14) 2_677 .
N2 C10 C10 121.9(2) 2_677 2_677
N1 C10 C10 121.2(2) . 2_677
N2 C11 C12 119.66(16) . .
N2 C11 C14 121.82(17) . .
C12 C11 C14 118.51(17) . .
C13 C12 C11 120.3(2) . .
C13 C12 H12 121.1(13) . .
C11 C12 H12 118.7(13) . .
C12 C13 C16 121.1(2) . .
C12 C13 H13 119.4 . .
C16 C13 H13 119.4 . .
N1 C14 C15 119.82(16) . .
N1 C14 C11 121.67(16) . .
C15 C14 C11 118.51(17) . .
C16 C15 C14 120.44(18) . .
C16 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C15 C16 C13 121.13(19) . .
C15 C16 H16 119.4 . .
C13 C16 H16 119.4 . .
C14 N1 C10 116.82(14) . .
C11 N2 C10 116.49(14) . 2_677
C6 C1 C2 118.67(15) . .
C6 C1 B1 119.82(16) . .
C2 C1 B1 121.47(16) . .
C3 C2 C1 119.54(16) . .
C3 C2 C7 119.48(17) . .
C1 C2 C7 120.98(16) . .
C4 C3 C2 122.02(16) . .
C4 C3 H3 119.0 . .
C2 C3 H3 119.0 . .
C5 C4 C3 117.93(16) . .
C5 C4 C8 121.06(19) . .
C3 C4 C8 121.01(18) . .
C4 C5 C6 121.87(17) . .
C4 C5 H5 119.1 . .
C6 C5 H5 119.1 . .
C5 C6 C1 119.95(16) . .
C5 C6 C9 119.62(17) . .
C1 C6 C9 120.43(16) . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C4 C8 H8A 109.5 . .
C4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
O2 B1 O1 118.04(16) . .
O2 B1 C1 120.78(17) . .
O1 B1 C1 121.17(16) . .
B1 O1 H1O 110.7(17) . .
B1 O2 H2O 114(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C10 N2 1.346(2) 2_677
C10 N1 1.346(2) .
C10 C10 1.436(3) 2_677
C11 N2 1.327(2) .
C11 C12 1.428(3) .
C11 C14 1.448(2) .
C12 C13 1.345(3) .
C12 H12 0.97(2) .
C13 C16 1.420(3) .
C13 H13 0.9300 .
C14 N1 1.330(2) .
C14 C15 1.424(3) .
C15 C16 1.344(3) .
C15 H15 0.9300 .
C16 H16 0.9300 .
N2 C10 1.346(2) 2_677
C1 C6 1.401(3) .
C1 C2 1.403(2) .
C1 B1 1.576(2) .
C2 C3 1.385(2) .
C2 C7 1.501(3) .
C3 C4 1.385(3) .
C3 H3 0.9300 .
C4 C5 1.378(3) .
C4 C8 1.512(2) .
C5 C6 1.385(2) .
C5 H5 0.9300 .
C6 C9 1.507(2) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
B1 O2 1.349(3) .
B1 O1 1.371(3) .
O1 H1O 0.89(3) .
O2 H2O 0.91(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125208
