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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/7/24/71/7247145.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_7247145
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            'C20 H15 B N2 O2'
_chemical_formula_weight         326.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.007(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0840(8)
_cell_length_b                   7.3311(5)
_cell_length_c                   21.0913(13)
_cell_measurement_reflns_used    2174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.72
_cell_measurement_theta_min      2.23
_cell_volume                     1692.7(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0587
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_min         2.233
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6039
_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            yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0109(19)
_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   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0514
_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)+(0.0594P)²+0.2328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1910
_reflns_number_total             3443
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra03936f2.cif
_cod_data_source_block           4Cyanophenylboronicacid_Acridine
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7247145
_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   0.965
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_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_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 0.41552(13) 0.8467(2) 0.53079(8) 0.0625(5) Uani 1 1 d . . . . .
H1 H 0.359489 0.795704 0.544938 0.094 Uiso 1 1 calc R U . . .
O2 O 0.62896(13) 0.8563(2) 0.54921(9) 0.0668(5) Uani 1 1 d . . . . .
H2A H 0.612681 0.951306 0.529144 0.100 Uiso 1 1 calc R U . . .
N1 N 0.18901(15) 0.7771(2) 0.55596(9) 0.0468(5) Uani 1 1 d . . . . .
N2 N 0.5771(2) -0.0485(3) 0.72519(13) 0.0912(8) Uani 1 1 d . . . . .
C1 C 0.15859(19) 0.8364(3) 0.61193(11) 0.0483(6) Uani 1 1 d . . . . .
C2 C 0.2532(2) 0.8792(3) 0.66320(13) 0.0655(7) Uani 1 1 d . . . . .
H2 H 0.334243 0.858996 0.658610 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2265(3) 0.9495(4) 0.71891(15) 0.0848(9) Uani 1 1 d . . . . .
H3 H 0.289634 0.979987 0.751614 0.102 Uiso 1 1 calc R U . . .
C4 C 0.1051(4) 0.9767(4) 0.72794(15) 0.0908(10) Uani 1 1 d . . . . .
H4 H 0.088684 1.024851 0.766479 0.109 Uiso 1 1 calc R U . . .
C5 C 0.0119(3) 0.9336(4) 0.68115(14) 0.0738(8) Uani 1 1 d . . . . .
H5 H -0.068172 0.950265 0.688123 0.089 Uiso 1 1 calc R U . . .
C6 C 0.0347(2) 0.8626(3) 0.62106(12) 0.0517(6) Uani 1 1 d . . . . .
C7 C -0.05636(19) 0.8244(3) 0.57019(13) 0.0545(6) Uani 1 1 d . . . . .
H7 H -0.137773 0.839399 0.574968 0.065 Uiso 1 1 calc R U . . .
C8 C -0.02760(18) 0.7641(3) 0.51223(12) 0.0470(6) Uani 1 1 d . . . . .
C9 C -0.1173(2) 0.7262(3) 0.45823(14) 0.0646(7) Uani 1 1 d . . . . .
H9 H -0.199608 0.740005 0.461232 0.077 Uiso 1 1 calc R U . . .
C10 C -0.0842(3) 0.6703(3) 0.40258(15) 0.0747(8) Uani 1 1 d . . . . .
H10 H -0.143886 0.645083 0.367555 0.090 Uiso 1 1 calc R U . . .
C11 C 0.0400(3) 0.6498(3) 0.39695(13) 0.0726(8) Uani 1 1 d . . . . .
H11 H 0.061111 0.611850 0.358066 0.087 Uiso 1 1 calc R U . . .
C12 C 0.1294(2) 0.6844(3) 0.44716(12) 0.0592(6) Uani 1 1 d . . . . .
H12 H 0.210935 0.669748 0.442587 0.071 Uiso 1 1 calc R U . . .
C13 C 0.09839(19) 0.7430(3) 0.50669(11) 0.0451(5) Uani 1 1 d . . . . .
C14 C 0.53488(18) 0.5860(3) 0.59523(11) 0.0475(6) Uani 1 1 d . . . . .
C15 C 0.44278(19) 0.4554(3) 0.58639(11) 0.0564(6) Uani 1 1 d . . . . .
H15 H 0.371528 0.479984 0.558085 0.068 Uiso 1 1 calc R U . . .
C16 C 0.4538(2) 0.2905(3) 0.61828(12) 0.0617(7) Uani 1 1 d . . . . .
H16 H 0.391349 0.204733 0.610964 0.074 Uiso 1 1 calc R U . . .
C17 C 0.55852(19) 0.2540(3) 0.66120(11) 0.0504(6) Uani 1 1 d . . . . .
C18 C 0.6518(2) 0.3809(3) 0.67162(12) 0.0589(6) Uani 1 1 d . . . . .
H18 H 0.722247 0.356875 0.700605 0.071 Uiso 1 1 calc R U . . .
C19 C 0.63906(19) 0.5435(3) 0.63850(12) 0.0578(7) Uani 1 1 d . . . . .
H19 H 0.702418 0.627858 0.645319 0.069 Uiso 1 1 calc R U . . .
C20 C 0.5693(2) 0.0846(4) 0.69664(13) 0.0639(7) Uani 1 1 d . . . . .
B1 B 0.5237(2) 0.7703(4) 0.55709(14) 0.0510(7) 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'
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 H2A 109.5 . . ?
C1 N1 C13 118.37(18) . . ?
N1 C1 C2 118.8(2) . . ?
N1 C1 C6 122.6(2) . . ?
C2 C1 C6 118.6(2) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 123.6(2) . . ?
C7 C6 C1 117.9(2) . . ?
C5 C6 C1 118.4(2) . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 122.9(2) . . ?
C7 C8 C13 118.1(2) . . ?
C9 C8 C13 119.0(2) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N1 C13 C12 118.9(2) . . ?
N1 C13 C8 122.4(2) . . ?
C12 C13 C8 118.7(2) . . ?
C19 C14 C15 116.8(2) . . ?
C19 C14 B1 121.39(19) . . ?
C15 C14 B1 121.8(2) . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 C20 119.9(2) . . ?
C18 C17 C20 119.8(2) . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C14 122.4(2) . . ?
C18 C19 H19 118.8 . . ?
C14 C19 H19 118.8 . . ?
N2 C20 C17 179.2(3) . . ?
O2 B1 O1 118.5(2) . . ?
O2 B1 C14 117.5(2) . . ?
O1 B1 C14 123.9(2) . . ?
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 1.360(3) . ?
O1 H1 0.8200 . ?
O2 B1 1.360(3) . ?
O2 H2A 0.8200 . ?
N1 C1 1.349(3) . ?
N1 C13 1.351(3) . ?
N2 C20 1.143(3) . ?
C1 C2 1.419(3) . ?
C1 C6 1.429(3) . ?
C2 C3 1.358(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.350(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.429(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(3) . ?
C8 C13 1.428(3) . ?
C9 C10 1.347(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.408(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.419(3) . ?
C12 H12 0.9300 . ?
C14 C19 1.390(3) . ?
C14 C15 1.391(3) . ?
C14 B1 1.568(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(3) . ?
C17 C20 1.445(3) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
