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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/4/12/58/4125811.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_4125811
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(C6 H5 B Cl2 O2), 2(C7 H8)'
_chemical_formula_sum            'C40 H34 B2 Cl4 N4 O4'
_chemical_formula_weight         798.13
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.143(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4226(10)
_cell_length_b                   25.677(4)
_cell_length_c                   10.9888(16)
_cell_measurement_reflns_used    1891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4770
_cell_measurement_theta_min      3.0250
_cell_volume                     1978.5(5)
_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    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 0.957
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7424
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  0.9500
_exptl_absorpt_correction_T_min  0.9065
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0740
_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)+(0.0955P)²+0.4628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.1997
_reflns_number_gt                2231
_reflns_number_total             3337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b11362_si_024.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4125811
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4385(4) 0.18173(12) 0.2104(3) 0.0493(8) Uani 1 1 d . . .
C2 C 0.4247(5) 0.21846(13) 0.1139(3) 0.0544(9) Uani 1 1 d . . .
C3 C 0.2718(5) 0.25241(15) 0.0692(4) 0.0695(11) Uani 1 1 d . . .
H3 H 0.2654 0.2759 0.0035 0.083 Uiso 1 1 calc R . .
C4 C 0.1294(6) 0.25066(17) 0.1240(5) 0.0790(12) Uani 1 1 d . . .
H4 H 0.0260 0.2732 0.0946 0.095 Uiso 1 1 calc R . .
C5 C 0.1376(5) 0.21649(17) 0.2206(4) 0.0732(11) Uani 1 1 d . . .
H5 H 0.0427 0.2159 0.2587 0.088 Uiso 1 1 calc R . .
C6 C 0.2905(5) 0.18280(15) 0.2604(3) 0.0605(9) Uani 1 1 d . . .
Cl1 Cl 0.60578(14) 0.22142(4) 0.04710(10) 0.0756(4) Uani 1 1 d . . .
Cl2 Cl 0.29545(19) 0.13908(5) 0.38210(11) 0.0974(5) Uani 1 1 d . . .
B1 B 0.6091(5) 0.14103(16) 0.2599(3) 0.0493(9) Uani 1 1 d . . .
O1 O 0.7629(4) 0.15483(11) 0.3571(3) 0.0758(9) Uani 1 1 d . . .
O2 O 0.5841(4) 0.09432(11) 0.2009(3) 0.0695(8) Uani 1 1 d . . .
H1O H 0.844(6) 0.1349(18) 0.389(4) 0.073(13) Uiso 1 1 d . . .
H2O H 0.673(7) 0.079(2) 0.236(4) 0.091(16) Uiso 1 1 d . . .
N1 N 0.6518(4) 0.51281(11) 0.1654(2) 0.0486(7) Uani 1 1 d . . .
N2 N 0.5041(4) 0.57093(11) 0.0052(2) 0.0484(7) Uani 1 1 d . . .
C7 C 0.8012(5) 0.45152(16) 0.3310(3) 0.0594(9) Uani 1 1 d . . .
H7 H 0.8519 0.4784 0.3889 0.071 Uiso 1 1 calc R . .
C8 C 0.8381(5) 0.40205(17) 0.3688(4) 0.0681(11) Uani 1 1 d . . .
H8 H 0.9143 0.3949 0.4529 0.082 Uiso 1 1 calc R . .
C9 C 0.7623(5) 0.35982(17) 0.2820(4) 0.0677(10) Uani 1 1 d . . .
H9 H 0.7909 0.3257 0.3105 0.081 Uiso 1 1 calc R . .
C10 C 0.6506(5) 0.36856(15) 0.1603(3) 0.0612(9) Uani 1 1 d . . .
H10 H 0.6019 0.3407 0.1051 0.073 Uiso 1 1 calc R . .
C11 C 0.6069(4) 0.42067(13) 0.1158(3) 0.0463(8) Uani 1 1 d . . .
C12 C 0.6852(4) 0.46335(14) 0.2032(3) 0.0470(8) Uani 1 1 d . . .
C13 C 0.5379(3) 0.52079(11) 0.0429(2) 0.0427(8) Uani 1 1 d . . .
C14 C 0.3344(3) 0.41981(11) 0.3976(2) 0.126(6) Uani 0.60 1 d PR A 1
C15 C 0.2887(3) 0.47181(11) 0.3679(2) 0.102(4) Uani 0.60 1 d PR A 1
H15 H 0.3203 0.4967 0.4329 0.123 Uiso 0.60 1 calc PR A 1
C16 C 0.1956(3) 0.48655(11) 0.2410(2) 0.107(4) Uani 0.60 1 d PR A 1
H16 H 0.1650 0.5213 0.2211 0.129 Uiso 0.60 1 calc PR A 1
C17 C 0.1483(3) 0.44928(11) 0.1439(2) 0.092(6) Uani 0.60 1 d PR A 1
H17 H 0.0860 0.4591 0.0590 0.110 Uiso 0.60 1 calc PR A 1
C18 C 0.1940(3) 0.39728(11) 0.1736(2) 0.109(4) Uani 0.60 1 d PR A 1
H18 H 0.1623 0.3724 0.1086 0.131 Uiso 0.60 1 calc PR A 1
C19 C 0.2870(3) 0.38254(11) 0.3005(2) 0.094(4) Uani 0.60 1 d PR A 1
H19 H 0.3176 0.3477 0.3204 0.113 Uiso 0.60 1 calc PR A 1
C20 C 0.4351(3) 0.39928(11) 0.5196(2) 0.155(6) Uani 0.60 1 d PR A 1
H20A H 0.5597 0.3885 0.5212 0.232 Uiso 0.60 1 calc PR A 1
H20B H 0.3673 0.3699 0.5368 0.232 Uiso 0.60 1 calc PR A 1
H20C H 0.4470 0.4255 0.5842 0.232 Uiso 0.60 1 calc PR A 1
C14' C 0.3050(3) 0.41180(11) 0.3457(2) 0.100(6) Uani 0.40 1 d PR A 2
C15' C 0.3235(3) 0.46182(11) 0.3967(2) 0.168(12) Uani 0.40 1 d PR A 2
H15' H 0.3851 0.4670 0.4843 0.202 Uiso 0.40 1 calc PR A 2
C16' C 0.2498(3) 0.50407(11) 0.3168(2) 0.163(11) Uani 0.40 1 d PR A 2
H16' H 0.2621 0.5375 0.3510 0.195 Uiso 0.40 1 calc PR A 2
C17' C 0.1576(3) 0.49632(11) 0.1859(2) 0.123(7) Uani 0.40 1 d PR A 2
H17' H 0.1083 0.5246 0.1325 0.147 Uiso 0.40 1 calc PR A 2
C18' C 0.1392(3) 0.44631(11) 0.1349(2) 0.166(16) Uani 0.40 1 d PR A 2
H18' H 0.0775 0.4411 0.0473 0.199 Uiso 0.40 1 calc PR A 2
C19' C 0.2129(3) 0.40405(11) 0.2147(2) 0.109(8) Uani 0.40 1 d PR A 2
H19' H 0.2005 0.3706 0.1806 0.130 Uiso 0.40 1 calc PR A 2
C20' C 0.4069(3) 0.36151(11) 0.4398(2) 0.192(13) Uani 0.40 1 d PR A 2
H20D H 0.5416 0.3675 0.4763 0.288 Uiso 0.40 1 calc PR A 2
H20E H 0.3846 0.3302 0.3894 0.288 Uiso 0.40 1 calc PR A 2
H20F H 0.3528 0.3580 0.5077 0.288 Uiso 0.40 1 calc PR A 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'
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'
Cl Cl 0.1484 0.1585 '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'
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
C6 C1 C2 114.8(3) . .
C6 C1 B1 121.6(3) . .
C2 C1 B1 123.6(3) . .
C3 C2 C1 122.7(3) . .
C3 C2 Cl1 118.8(3) . .
C1 C2 Cl1 118.5(3) . .
C4 C3 C2 118.7(4) . .
C4 C3 H3 120.6 . .
C2 C3 H3 120.6 . .
C5 C4 C3 121.1(4) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C6 118.2(4) . .
C4 C5 H5 120.9 . .
C6 C5 H5 120.9 . .
C5 C6 C1 124.5(3) . .
C5 C6 Cl2 117.2(3) . .
C1 C6 Cl2 118.3(3) . .
O1 B1 O2 124.8(3) . .
O1 B1 C1 118.4(3) . .
O2 B1 C1 116.8(3) . .
B1 O1 H1O 121(3) . .
B1 O2 H2O 105(4) . .
C12 N1 C13 116.5(2) . .
C11 N2 C13 116.9(3) 3_665 .
C8 C7 C12 120.5(3) . .
C8 C7 H7 119.8 . .
C12 C7 H7 119.8 . .
C7 C8 C9 121.1(3) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
C10 C9 C8 121.1(4) . .
C10 C9 H9 119.4 . .
C8 C9 H9 119.4 . .
C9 C10 C11 119.7(4) . .
C9 C10 H10 120.1 . .
C11 C10 H10 120.1 . .
N2 C11 C10 119.4(3) 3_665 .
N2 C11 C12 121.5(3) 3_665 .
C10 C11 C12 119.1(3) . .
N1 C12 C7 120.2(3) . .
N1 C12 C11 121.4(3) . .
C7 C12 C11 118.4(3) . .
N1 C13 N2 116.3(2) . .
N1 C13 C13 122.2(3) . 3_665
N2 C13 C13 121.5(3) . 3_665
C15 C14 C19 120.0 . .
C15 C14 C20 126.6 . .
C19 C14 C20 113.3 . .
C14 C15 C16 120.0 . .
C14 C15 H15 120.0 . .
C16 C15 H15 120.0 . .
C15 C16 C17 120.0 . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
C18 C17 C16 120.0 . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C19 120.0 . .
C17 C18 H18 120.0 . .
C19 C18 H18 120.0 . .
C18 C19 C14 120.0 . .
C18 C19 H19 120.0 . .
C14 C19 H19 120.0 . .
C15' C14' C19' 120.0 . .
C15' C14' C20' 119.9 . .
C19' C14' C20' 119.9 . .
C16' C15' C14' 120.0 . .
C16' C15' H15' 120.0 . .
C14' C15' H15' 120.0 . .
C15' C16' C17' 120.0 . .
C15' C16' H16' 120.0 . .
C17' C16' H16' 120.0 . .
C16' C17' C18' 120.0 . .
C16' C17' H17' 120.0 . .
C18' C17' H17' 120.0 . .
C19' C18' C17' 120.0 . .
C19' C18' H18' 120.0 . .
C17' C18' H18' 120.0 . .
C18' C19' C14' 120.0 . .
C18' C19' H19' 120.0 . .
C14' C19' H19' 120.0 . .
C14' C20' H20D 109.5 . .
C14' C20' H20E 109.5 . .
H20D C20' H20E 109.5 . .
C14' C20' H20F 109.5 . .
H20D C20' H20F 109.5 . .
H20E C20' H20F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.381(5) .
C1 C2 1.398(5) .
C1 B1 1.594(5) .
C2 C3 1.387(5) .
C2 Cl1 1.731(4) .
C3 C4 1.378(6) .
C3 H3 0.9300 .
C4 C5 1.363(6) .
C4 H4 0.9300 .
C5 C6 1.379(5) .
C5 H5 0.9300 .
C6 Cl2 1.737(4) .
B1 O1 1.330(5) .
B1 O2 1.347(5) .
O1 H1O 0.78(4) .
O2 H2O 0.76(5) .
N1 C12 1.334(4) .
N1 C13 1.350(3) .
N2 C11 1.333(4) 3_665
N2 C13 1.351(4) .
C7 C8 1.336(5) .
C7 C12 1.419(4) .
C7 H7 0.9300 .
C8 C9 1.432(6) .
C8 H8 0.9300 .
C9 C10 1.341(5) .
C9 H9 0.9300 .
C10 C11 1.425(5) .
C10 H10 0.9300 .
C11 N2 1.333(4) 3_665
C11 C12 1.448(4) .
C13 C13 1.414(5) 3_665
C14 C15 1.3900 .
C14 C19 1.3900 .
C14 C20 1.4060 .
C15 C16 1.3900 .
C15 H15 0.9300 .
C16 C17 1.3900 .
C16 H16 0.9300 .
C17 C18 1.3900 .
C17 H17 0.9300 .
C18 C19 1.3900 .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C14' C15' 1.3900 .
C14' C19' 1.3900 .
C14' C20' 1.6720 .
C15' C16' 1.3900 .
C15' H15' 0.9300 .
C16' C17' 1.3900 .
C16' H16' 0.9300 .
C17' C18' 1.3900 .
C17' H17' 0.9300 .
C18' C19' 1.3900 .
C18' H18' 0.9300 .
C19' H19' 0.9300 .
C20' H20D 0.9600 .
C20' H20E 0.9600 .
C20' H20F 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -1.7(5) . .
B1 C1 C2 C3 177.8(3) . .
C6 C1 C2 Cl1 178.6(2) . .
B1 C1 C2 Cl1 -1.9(4) . .
C1 C2 C3 C4 1.4(5) . .
Cl1 C2 C3 C4 -178.8(3) . .
C2 C3 C4 C5 0.2(6) . .
C3 C4 C5 C6 -1.4(6) . .
C4 C5 C6 C1 1.1(6) . .
C4 C5 C6 Cl2 -179.1(3) . .
C2 C1 C6 C5 0.4(5) . .
B1 C1 C6 C5 -179.1(3) . .
C2 C1 C6 Cl2 -179.4(3) . .
B1 C1 C6 Cl2 1.1(4) . .
C6 C1 B1 O1 -90.9(4) . .
C2 C1 B1 O1 89.7(4) . .
C6 C1 B1 O2 87.8(4) . .
C2 C1 B1 O2 -91.6(4) . .
C12 C7 C8 C9 0.1(6) . .
C7 C8 C9 C10 -0.5(6) . .
C8 C9 C10 C11 0.3(6) . .
C9 C10 C11 N2 180.0(3) . 3_665
C9 C10 C11 C12 0.3(5) . .
C13 N1 C12 C7 -179.1(3) . .
C13 N1 C12 C11 1.7(4) . .
C8 C7 C12 N1 -178.7(3) . .
C8 C7 C12 C11 0.6(5) . .
N2 C11 C12 N1 -1.2(4) 3_665 .
C10 C11 C12 N1 178.5(3) . .
N2 C11 C12 C7 179.6(3) 3_665 .
C10 C11 C12 C7 -0.8(4) . .
C12 N1 C13 N2 179.8(2) . .
C12 N1 C13 C13 -2.1(4) . 3_665
C11 N2 C13 N1 179.4(2) 3_665 .
C11 N2 C13 C13 1.3(4) 3_665 3_665
C19 C14 C15 C16 0.0 . .
C20 C14 C15 C16 177.0 . .
C14 C15 C16 C17 0.0 . .
C15 C16 C17 C18 0.0 . .
C16 C17 C18 C19 0.0 . .
C17 C18 C19 C14 0.0 . .
C15 C14 C19 C18 0.0 . .
C20 C14 C19 C18 -177.4 . .
C19' C14' C15' C16' 0.0 . .
C20' C14' C15' C16' 175.7 . .
C14' C15' C16' C17' 0.0 . .
C15' C16' C17' C18' 0.0 . .
C16' C17' C18' C19' 0.0 . .
C17' C18' C19' C14' 0.0 . .
C15' C14' C19' C18' 0.0 . .
C20' C14' C19' C18' -175.7 . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125198
