#------------------------------------------------------------------------------
#$Date: 2023-08-03 04:22:23 +0300 (Thu, 03 Aug 2023) $
#$Revision: 285435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247153.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_7247153
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            'C19 H20 B N3 O3'
_chemical_formula_weight         349.19
_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
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                99.982(5)
_cell_angle_beta                 102.829(4)
_cell_angle_gamma                105.296(7)
_cell_formula_units_Z            2
_cell_length_a                   7.5470(4)
_cell_length_b                   11.5173(7)
_cell_length_c                   11.9183(8)
_cell_measurement_reflns_used    5679
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.27
_cell_volume                     944.22(11)
_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 0.997
_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  0.0959
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26286
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.678
_diffrn_reflns_theta_min         1.808
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6250
_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            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       rod
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0645
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0731P)²+0.3460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.1955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2355
_reflns_number_total             3941
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra03936f2.cif
_cod_data_source_block           4Cyanophenylboronicacid_12bis(4pyridyl)ethane
_cod_database_code               7247153
_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   0.957
_shelx_estimated_absorpt_t_max   0.984
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 0.5817(3) 0.1962(2) 0.29630(17) 0.0902(6) Uani 1 1 d . . . . .
H1 H 0.600338 0.198347 0.231364 0.135 Uiso 1 1 calc R U . . .
O2 O 0.7002(3) 0.1345(2) 0.46559(16) 0.0843(6) Uani 1 1 d . . . . .
H2A H 0.630313 0.171322 0.488368 0.126 Uiso 1 1 calc R U . . .
O3 O 0.5527(4) 0.2310(3) 0.0764(2) 0.1096(9) Uani 1 1 d . . . . .
N1 N 0.4684(3) 0.2482(2) 0.5603(2) 0.0725(6) Uani 1 1 d . . . . .
N2 N -0.3073(4) 0.6285(2) 0.8963(2) 0.0883(7) Uani 1 1 d . . . . .
N3 N 1.2748(4) -0.1443(2) 0.1073(2) 0.0916(8) Uani 1 1 d . . . . .
C1 C 0.8270(3) 0.0758(2) 0.2952(2) 0.0580(6) Uani 1 1 d . . . . .
C2 C 0.9914(4) 0.0643(2) 0.3664(2) 0.0663(6) Uani 1 1 d . . . . .
H2 H 1.022790 0.094783 0.448255 0.080 Uiso 1 1 calc R U . . .
C3 C 1.1094(4) 0.0092(2) 0.3196(2) 0.0681(7) Uani 1 1 d . . . . .
H3 H 1.219992 0.004260 0.368951 0.082 Uiso 1 1 calc R U . . .
C4 C 1.0610(3) -0.0384(2) 0.1987(2) 0.0595(6) Uani 1 1 d . . . . .
C5 C 0.8958(3) -0.0304(2) 0.1248(2) 0.0620(6) Uani 1 1 d . . . . .
H5 H 0.862434 -0.063604 0.043290 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7819(3) 0.0275(2) 0.1738(2) 0.0620(6) Uani 1 1 d . . . . .
H6 H 0.672880 0.034108 0.124191 0.074 Uiso 1 1 calc R U . . .
C7 C 1.1814(4) -0.0973(2) 0.1481(2) 0.0692(7) Uani 1 1 d . . . . .
C8 C 0.4106(4) 0.2202(3) 0.6510(3) 0.0814(8) Uani 1 1 d . . . . .
H8 H 0.452243 0.161655 0.684768 0.098 Uiso 1 1 calc R U . . .
C9 C 0.2923(5) 0.2725(3) 0.6987(3) 0.1027(11) Uani 1 1 d . . . . .
H9 H 0.254116 0.248280 0.762351 0.123 Uiso 1 1 calc R U . . .
C10 C 0.2304(7) 0.3599(4) 0.6532(4) 0.1296(15) Uani 1 1 d . . . . .
C11 C 0.2904(7) 0.3879(4) 0.5591(4) 0.1358(16) Uani 1 1 d . . . . .
H11 H 0.252342 0.446907 0.524169 0.163 Uiso 1 1 calc R U . . .
C12 C 0.4056(5) 0.3306(3) 0.5153(3) 0.1002(11) Uani 1 1 d . . . . .
H12 H 0.441852 0.351076 0.449815 0.120 Uiso 1 1 calc R U . . .
C15 C -0.2968(5) 0.5196(3) 0.9074(3) 0.0984(10) Uani 1 1 d . . . . .
H15 H -0.369056 0.479349 0.951373 0.118 Uiso 1 1 calc R U . . .
C16 C -0.1868(6) 0.4613(3) 0.8587(4) 0.1143(13) Uani 1 1 d . . . . .
H16 H -0.184411 0.383994 0.870757 0.137 Uiso 1 1 calc R U . . .
C17 C -0.0819(6) 0.5147(4) 0.7934(4) 0.1229(14) Uani 1 1 d . . . . .
C18 C -0.0907(6) 0.6278(4) 0.7808(4) 0.1228(14) Uani 1 1 d . . . . .
H18 H -0.019303 0.669832 0.737453 0.147 Uiso 1 1 calc R U . . .
C19 C -0.2058(6) 0.6796(3) 0.8326(4) 0.1070(11) Uani 1 1 d . . . . .
H19 H -0.211600 0.756582 0.821434 0.128 Uiso 1 1 calc R U . . .
B1 B 0.6942(4) 0.1387(3) 0.3530(3) 0.0639(7) Uani 1 1 d . . . . .
H4 H 0.488(6) 0.277(4) 0.069(4) 0.137(15) Uiso 1 1 d . . . . .
H7 H 0.579(6) 0.216(4) 0.013(4) 0.133(15) Uiso 1 1 d . . . . .
C13A C 0.037(2) 0.3896(14) 0.6677(11) 0.123(5) Uani 0.44(2) 1 d . . P A 1
H13A H -0.014134 0.425753 0.605136 0.148 Uiso 0.44(2) 1 calc R U P A 1
H13B H -0.061048 0.315277 0.667382 0.148 Uiso 0.44(2) 1 calc R U P A 1
C14A C 0.104(2) 0.4772(11) 0.7815(11) 0.113(5) Uani 0.413(19) 1 d . . P A 1
H14A H 0.207311 0.548937 0.783253 0.136 Uiso 0.413(19) 1 calc R U P A 1
H14B H 0.146916 0.439333 0.844502 0.136 Uiso 0.413(19) 1 calc R U P A 1
C13B C 0.160(2) 0.4471(13) 0.7342(17) 0.195(7) Uani 0.56(2) 1 d . . P A 2
H13C H 0.194312 0.435855 0.814082 0.234 Uiso 0.56(2) 1 calc R U P A 2
H13D H 0.227407 0.532385 0.737090 0.234 Uiso 0.56(2) 1 calc R U P A 2
C14B C -0.0102(19) 0.4311(12) 0.7034(16) 0.172(5) Uani 0.587(19) 1 d . . P A 2
H14C H -0.077981 0.344346 0.694589 0.206 Uiso 0.587(19) 1 calc R U P A 2
H14D H -0.043151 0.448933 0.626203 0.206 Uiso 0.587(19) 1 calc R U 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
C12 N1 C8 116.2(2) . . ?
C19 N2 C15 115.3(2) . . ?
C6 C1 C2 117.6(2) . . ?
C6 C1 B1 121.9(2) . . ?
C2 C1 B1 120.4(2) . . ?
C3 C2 C1 122.1(2) . . ?
C4 C3 C2 119.1(2) . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 C7 119.9(2) . . ?
C5 C4 C7 119.6(2) . . ?
C6 C5 C4 119.3(2) . . ?
C5 C6 C1 121.4(2) . . ?
N3 C7 C4 179.3(3) . . ?
N1 C8 C9 123.5(3) . . ?
C10 C9 C8 120.2(3) . . ?
C11 C10 C9 115.9(3) . . ?
C11 C10 C13B 123.6(6) . . ?
C9 C10 C13B 117.2(7) . . ?
C11 C10 C13A 116.6(6) . . ?
C9 C10 C13A 123.1(6) . . ?
C10 C11 C12 120.6(3) . . ?
N1 C12 C11 123.7(3) . . ?
N2 C15 C16 124.1(3) . . ?
C17 C16 C15 120.2(3) . . ?
C16 C17 C18 116.6(3) . . ?
C16 C17 C14B 119.4(5) . . ?
C18 C17 C14B 121.0(6) . . ?
C16 C17 C14A 119.1(5) . . ?
C18 C17 C14A 119.3(6) . . ?
C17 C18 C19 119.3(3) . . ?
N2 C19 C18 124.4(3) . . ?
O2 B1 O1 119.7(2) . . ?
O2 B1 C1 116.5(2) . . ?
O1 B1 C1 123.8(2) . . ?
C14A C13A C10 102.2(11) . . ?
C13A C14A C17 103.0(11) . . ?
C14B C13B C10 114.7(17) . . ?
C13B C14B C17 113.9(16) . . ?
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 1.346(3) . ?
O2 B1 1.343(3) . ?
N1 C12 1.308(4) . ?
N1 C8 1.311(3) . ?
N2 C19 1.298(4) . ?
N2 C15 1.304(4) . ?
N3 C7 1.136(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.391(3) . ?
C1 B1 1.587(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.393(3) . ?
C4 C7 1.441(3) . ?
C5 C6 1.383(3) . ?
C8 C9 1.369(4) . ?
C9 C10 1.360(5) . ?
C10 C11 1.357(5) . ?
C10 C13B 1.548(12) . ?
C10 C13A 1.625(13) . ?
C11 C12 1.360(4) . ?
C15 C16 1.361(4) . ?
C16 C17 1.339(5) . ?
C17 C18 1.353(5) . ?
C17 C14B 1.596(13) . ?
C17 C14A 1.598(12) . ?
C18 C19 1.370(4) . ?
C13A C14A 1.44(2) . ?
C13B C14B 1.21(2) . ?
