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#$Date: 2023-08-03 04:22:23 +0300 (Thu, 03 Aug 2023) $
#$Revision: 285435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247152.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_7247152
loop_
_publ_author_name
'Easmin, Samina'
'Pedireddi, Venkateswara Rao'
_publ_section_title
;
 Supramolecular assemblies in the molecular complexes of
 4-cyanophenylboronic acid with different N-donor ligands
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              23267
_journal_page_last               23284
_journal_paper_doi               10.1039/D3RA03936F
_journal_volume                  13
_journal_year                    2023
_chemical_formula_sum            'C17 H16 B N5 O3'
_chemical_formula_weight         349.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-04 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                105.5490(10)
_cell_angle_beta                 108.761(3)
_cell_angle_gamma                90.865(6)
_cell_formula_units_Z            2
_cell_length_a                   8.8653(3)
_cell_length_b                   9.0872(4)
_cell_length_c                   12.2227(5)
_cell_measurement_reflns_used    4572
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.39
_cell_measurement_theta_min      2.34
_cell_volume                     892.67(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25898
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.544
_diffrn_reflns_theta_min         2.341
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.057(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0791P)²+0.1490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1796
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1990
_reflns_number_total             3672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra03936f2.cif
_cod_data_source_block           4Cyanophenylboronicacid_Azopyridine_hydrate
_cod_original_cell_volume        892.67(6)
_cod_database_code               7247152
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8333(2) 0.1499(2) 0.54252(15) 0.0852(5) Uani 1 1 d . . . . .
H1 H 0.854117 0.165931 0.485753 0.128 Uiso 1 1 calc R U . . .
O2 O 0.6164(2) 0.2901(2) 0.47570(17) 0.1006(6) Uani 1 1 d . . . . .
H2 H 0.668293 0.303509 0.433787 0.151 Uiso 1 1 calc R U . . .
O3 O 0.0287(3) 0.1009(4) 0.4072(3) 0.1441(10) Uani 1 1 d G . . . .
H3A H 0.040107 0.141542 0.376624 0.216 Uiso 1 1 d G U . . .
H4A H 0.055151 0.007950 0.395019 0.49(6) Uiso 1 1 d G . . . .
N1 N 0.3181(3) 0.0560(3) 0.9289(2) 0.0976(7) Uani 1 1 d . . . . .
N2 N 0.2759(4) 0.6164(3) -0.3110(3) 0.1003(8) Uani 1 1 d . . . . .
N3 N 0.1161(3) 0.2439(3) 0.2593(3) 0.0944(7) Uani 1 1 d . . . . .
C1 C 0.6094(3) 0.1630(2) 0.63062(18) 0.0615(6) Uani 1 1 d . . . . .
C2 C 0.4518(3) 0.1893(3) 0.6156(2) 0.0748(6) Uani 1 1 d . . . . .
H2A H 0.395868 0.229592 0.553688 0.090 Uiso 1 1 calc R U . . .
C3 C 0.3756(3) 0.1575(3) 0.6896(2) 0.0767(7) Uani 1 1 d . . . . .
H3 H 0.268667 0.173788 0.676271 0.092 Uiso 1 1 calc R U . . .
C4 C 0.4576(3) 0.1014(2) 0.78339(19) 0.0647(6) Uani 1 1 d . . . . .
C5 C 0.6139(3) 0.0732(3) 0.8009(2) 0.0763(7) Uani 1 1 d . . . . .
H5 H 0.669584 0.034384 0.863766 0.092 Uiso 1 1 calc R U . . .
C6 C 0.6877(3) 0.1032(3) 0.72422(19) 0.0728(6) Uani 1 1 d . . . . .
H6 H 0.793217 0.082652 0.735739 0.087 Uiso 1 1 calc R U . . .
C7 C 0.3786(3) 0.0748(3) 0.8640(2) 0.0761(7) Uani 1 1 d . . . . .
C8 C 0.1596(4) 0.5070(4) -0.3413(3) 0.1066(10) Uani 1 1 d . . . . .
H8 H 0.097281 0.469209 -0.422339 0.128 Uiso 1 1 calc R U . . .
C9 C 0.1242(3) 0.4448(3) -0.2609(3) 0.0934(8) Uani 1 1 d . . . . .
H9 H 0.039528 0.367986 -0.286281 0.112 Uiso 1 1 calc R U . . .
C10 C 0.2164(3) 0.4987(3) -0.1432(2) 0.0749(7) Uani 1 1 d . . . . .
C11 C 0.3385(3) 0.6105(3) -0.1098(2) 0.0852(7) Uani 1 1 d . . . . .
H11 H 0.404206 0.648233 -0.029547 0.102 Uiso 1 1 calc R U . . .
C12 C 0.3629(4) 0.6664(3) -0.1959(3) 0.0952(9) Uani 1 1 d . . . . .
H12 H 0.445839 0.744426 -0.172153 0.114 Uiso 1 1 calc R U . . .
C13 C 0.0276(4) 0.1942(3) 0.1431(4) 0.0976(9) Uani 1 1 d . . . . .
H13 H -0.055042 0.115835 0.119140 0.117 Uiso 1 1 calc R U . . .
C14 C 0.0516(4) 0.2523(3) 0.0564(3) 0.0929(8) Uani 1 1 d . . . . .
H14 H -0.012806 0.213821 -0.024141 0.112 Uiso 1 1 calc R U . . .
C15 C 0.1710(4) 0.3666(3) 0.0912(3) 0.0819(8) Uani 1 1 d . . . . .
C16 C 0.2617(3) 0.4185(3) 0.2091(3) 0.0905(8) Uani 1 1 d . . . . .
H16 H 0.344377 0.497465 0.235234 0.109 Uiso 1 1 calc R U . . .
C17 C 0.2309(4) 0.3536(4) 0.2897(3) 0.0959(8) Uani 1 1 d . . . . .
H17 H 0.295345 0.389780 0.370339 0.115 Uiso 1 1 calc R U . . .
B1 B 0.6912(3) 0.2012(3) 0.5438(2) 0.0685(7) Uani 1 1 d . . . . .
N5 N 0.1288(16) 0.3842(16) -0.0307(15) 0.064(4) Uani 0.28(2) 1 d . . P A 1
N6 N 0.2510(17) 0.4820(16) -0.0223(17) 0.064(4) Uani 0.27(3) 1 d . . P A 1
N5A N 0.1533(7) 0.4140(7) -0.0761(9) 0.080(2) Uani 0.72(2) 1 d . . P A 2
N6A N 0.2367(7) 0.4544(6) 0.0255(10) 0.080(2) Uani 0.73(3) 1 d . . P 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'
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'
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
_geom_angle_publ_flag
B1 O1 H1 109.5 . . ?
B1 O2 H2 109.5 . . ?
H3A O3 H4A 120.1 . . ?
C8 N2 C12 116.5(2) . . ?
C17 N3 C13 116.6(2) . . ?
C2 C1 C6 116.98(19) . . ?
C2 C1 B1 119.9(2) . . ?
C6 C1 B1 123.1(2) . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2A 119.1 . . ?
C1 C2 H2A 119.1 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.04(19) . . ?
C5 C4 C7 120.5(2) . . ?
C3 C4 C7 119.5(2) . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 122.1(2) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
N1 C7 C4 178.8(3) . . ?
N2 C8 C9 124.0(3) . . ?
N2 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 N6 145.9(7) . . ?
C11 C10 N6 94.7(7) . . ?
C9 C10 N5A 107.1(3) . . ?
C11 C10 N5A 133.5(4) . . ?
C10 C11 C12 118.5(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
N2 C12 C11 123.7(3) . . ?
N2 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
N3 C13 C14 123.6(3) . . ?
N3 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C15 C14 C13 118.2(3) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 118.8(2) . . ?
C14 C15 N5 92.8(7) . . ?
C16 C15 N5 148.2(7) . . ?
C14 C15 N6A 134.1(4) . . ?
C16 C15 N6A 107.1(4) . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
N3 C17 C16 123.4(3) . . ?
N3 C17 H17 118.3 . . ?
C16 C17 H17 118.3 . . ?
O2 B1 O1 122.8(2) . . ?
O2 B1 C1 116.9(2) . . ?
O1 B1 C1 120.3(2) . . ?
N6 N5 C15 103.6(13) . . ?
N5 N6 C10 105.4(13) . . ?
N6A N5A C10 108.0(9) . . ?
N5A N6A C15 106.9(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.354(3) . ?
O1 H1 0.8200 . ?
O2 B1 1.344(3) . ?
O2 H2 0.8200 . ?
O3 H3A 0.6191 . ?
O3 H4A 0.8673 . ?
N1 C7 1.135(3) . ?
N2 C8 1.310(4) . ?
N2 C12 1.315(4) . ?
N3 C17 1.302(4) . ?
N3 C13 1.328(4) . ?
C1 C2 1.382(3) . ?
C1 C6 1.386(3) . ?
C1 B1 1.568(3) . ?
C2 C3 1.373(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 C7 1.445(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.369(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.352(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.353(4) . ?
C10 N6 1.46(2) . ?
C10 N5A 1.483(14) . ?
C11 C12 1.357(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.349(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.351(4) . ?
C15 N5 1.47(2) . ?
C15 N6A 1.500(13) . ?
C16 C17 1.367(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N5 N6 1.35(3) . ?
N5A N6A 1.175(13) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(4) . . . . ?
B1 C1 C2 C3 180.0(2) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C2 C3 C4 C5 -1.8(4) . . . . ?
C2 C3 C4 C7 177.2(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C7 C4 C5 C6 -178.4(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
B1 C1 C6 C5 178.7(2) . . . . ?
C12 N2 C8 C9 0.6(5) . . . . ?
N2 C8 C9 C10 -0.8(5) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C8 C9 C10 N6 -174.8(7) . . . . ?
C8 C9 C10 N5A 179.8(3) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
N6 C10 C11 C12 178.0(4) . . . . ?
N5A C10 C11 C12 -178.8(3) . . . . ?
C8 N2 C12 C11 0.3(4) . . . . ?
C10 C11 C12 N2 -1.1(4) . . . . ?
C17 N3 C13 C14 -0.1(4) . . . . ?
N3 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C13 C14 C15 N5 -176.0(4) . . . . ?
C13 C14 C15 N6A 177.7(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
N5 C15 C16 C17 173.1(7) . . . . ?
N6A C15 C16 C17 -177.8(2) . . . . ?
C13 N3 C17 C16 0.6(4) . . . . ?
C15 C16 C17 N3 -0.8(4) . . . . ?
C2 C1 B1 O2 14.7(3) . . . . ?
C6 C1 B1 O2 -165.1(2) . . . . ?
C2 C1 B1 O1 -167.5(2) . . . . ?
C6 C1 B1 O1 12.7(4) . . . . ?
C14 C15 N5 N6 -171.3(6) . . . . ?
C16 C15 N5 N6 15.0(11) . . . . ?
C15 N5 N6 C10 178.2(5) . . . . ?
C9 C10 N6 N5 -11.3(12) . . . . ?
C11 C10 N6 N5 173.2(6) . . . . ?
C9 C10 N5A N6A 176.8(3) . . . . ?
C11 C10 N5A N6A -3.5(5) . . . . ?
C10 N5A N6A C15 -179.7(2) . . . . ?
C14 C15 N6A N5A 5.3(5) . . . . ?
C16 C15 N6A N5A -177.0(3) . . . . ?
