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#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/24/2242404.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242404
loop_
_publ_author_name
'Cárdenas-Valenzuela, A. Jaquelin'
'González-García, Gerardo'
'Zárraga- Nuñez, Ramón'
'Höpfl, Herbert'
'Campos-Gaxiola, José J.'
'Cruz-Enríquez, Adriana'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of 3-cyanophenylboronic
 acid
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              441
_journal_page_last               444
_journal_paper_doi               10.1107/S2056989018003146
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C7 H6 B N O2'
_chemical_formula_moiety         'C7 H6 B N O2'
_chemical_formula_sum            'C7 H6 B N O2'
_chemical_formula_weight         146.94
_chemical_name_systematic
;
3-Cyanophenylboronic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 93.472(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8064(2)
_cell_length_b                   16.1560(10)
_cell_length_c                   11.4585(4)
_cell_measurement_reflns_used    4312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0530
_cell_measurement_theta_min      4.3500
_cell_volume                     703.36(6)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee,
2008;
Palatinus et al.,  2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0945
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
;
Rigaku OD SuperNova Single source at offset EosS2
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7332
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.563
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.199
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0422
_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)+(0.0566P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                1347
_reflns_number_total             1434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5425sup1.cif
_cod_data_source_block           I
_cod_database_code               2242404
_cod_database_fobs_code          2242404
_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   0.954
_shelx_estimated_absorpt_t_max   0.980
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O2 0.8906(3) 0.49351(6) 0.34935(8) 0.0436(3) Uani d 1
H H2 0.881271 0.482459 0.279381 0.065 Uiso calc 1
O O1 0.8143(3) 0.60701(6) 0.47187(8) 0.0507(3) Uani d 1
H H1 0.900315 0.572989 0.518407 0.076 Uiso calc 1
N N1 0.0762(4) 0.58588(8) -0.12243(11) 0.0485(4) Uani d 1
C C3 0.3424(3) 0.65006(8) 0.06942(10) 0.0307(3) Uani d 1
C C7 0.1909(4) 0.61462(8) -0.03743(11) 0.0355(3) Uani d 1
C C1 0.6246(3) 0.62961(8) 0.26214(10) 0.0302(3) Uani d 1
C C2 0.4765(3) 0.59744(8) 0.15775(11) 0.0309(3) Uani d 1
H H2A 0.467006 0.540428 0.146805 0.037 Uiso calc 1
C C4 0.3561(4) 0.73542(8) 0.08286(12) 0.0367(3) Uani d 1
H H4 0.267843 0.770116 0.023320 0.044 Uiso calc 1
C C6 0.6325(4) 0.71575(8) 0.27423(11) 0.0352(3) Uani d 1
H H6 0.727616 0.738593 0.343630 0.042 Uiso calc 1
C C5 0.5031(4) 0.76802(8) 0.18615(12) 0.0400(3) Uani d 1
H H5 0.515094 0.825073 0.196425 0.048 Uiso calc 1
B B1 0.7827(4) 0.57324(9) 0.36442(12) 0.0336(3) Uani d 1
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -16 11 0.1521
-5 3 1 0.2929
0 16 -11 0.0462
5 1 -5 0.1089
0 1 16 0.1849
-5 -1 2 0.2968
0 -1 -16 0.0978
0 -19 -9 0.0649
0 19 9 0.1485
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C3 C7 119.00(12)
C4 C3 C7 119.98(11)
C4 C3 C2 121.02(12)
N1 C7 C3 178.81(15)
C2 C1 C6 117.51(11)
C2 C1 B1 122.70(11)
C6 C1 B1 119.79(11)
C1 C2 C3 120.50(12)
C5 C4 C3 118.95(12)
C5 C6 C1 122.04(12)
C4 C5 C6 119.98(12)
O2 B1 C1 123.75(11)
O1 B1 O2 119.15(12)
O1 B1 C1 117.10(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 B1 1.3661(18)
O1 B1 1.3455(17)
N1 C7 1.1416(18)
C3 C7 1.4401(18)
C3 C2 1.3948(17)
C3 C4 1.3882(19)
C1 C2 1.3917(17)
C1 C6 1.3987(18)
C1 B1 1.5747(18)
C4 C5 1.3825(19)
C6 C5 1.3834(19)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O2 3_766 0.82 1.98 2.7960(10) 170
O2 H2 N1 3_665 0.82 2.12 2.909(2) 160
C2 H2A N1 3_665 0.93 2.71 3.452(2) 138
C4 H4 O1 4_475 0.93 2.67 3.469(2) 144
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
C3 C4 C5 C6 -0.2(2)
C7 C3 C2 C1 -179.96(12)
C7 C3 C4 C5 -179.92(12)
C1 C6 C5 C4 0.9(2)
C2 C3 C4 C5 -0.5(2)
C2 C1 C6 C5 -0.8(2)
C2 C1 B1 O2 21.3(2)
C2 C1 B1 O1 -159.37(13)
C4 C3 C2 C1 0.64(19)
C6 C1 C2 C3 0.00(18)
C6 C1 B1 O2 -158.17(13)
C6 C1 B1 O1 21.14(19)
B1 C1 C2 C3 -179.50(12)
B1 C1 C6 C5 178.76(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 2734325
