#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232109.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_7232109
loop_
_publ_author_name
'Dhami, Jaya K.'
'Idzorek, Kiersten M.'
'Johnson, Ryan B.'
'Van Auken, Kaitlyn S.'
'Ojala, William H.'
_publ_section_title
;
 Intramolecular geometry and intermolecular interactions of the CNO group
 of crystalline benzonitrile oxides: a comparison with phenyl cyanates,
 phenyl isocyanates, and phenyl azides
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              908
_journal_paper_doi               10.1039/C8CE02008F
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C7 H4 Br N O'
_chemical_formula_weight         198.02
_chemical_melting_point          374(3)
_chemical_name_common            '3-bromobenzonitrile oxide'
_chemical_name_systematic        3-bromobenzonitrile-N-oxide
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-19 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.068(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.671(15)
_cell_length_b                   3.903(2)
_cell_length_c                   14.123(8)
_cell_measurement_reflns_used    2294
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      3.00
_cell_volume                     1359.8(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'PLATON (Spek, 2009) Mercury (Allen et al, 2004)'
_computing_publication_material  'Bruker SHELXTL enCIFer (Allen et al, 2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0767
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5423
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.333
_diffrn_reflns_theta_min         1.651
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    5.962
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.7455
_exptl_transmission_factor_min   0.4301
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0434
_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)+(0.0508P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                980
_reflns_number_total             1379
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce02008f2.cif
_cod_data_source_block           15150a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '372-377 K' was changed to '374(3)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7232108--7232111.cif.
;
_cod_original_cell_volume        1359.9(14)
_cod_database_code               7232109
_shelx_shelxl_version_number     2014/7
_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   0.154
_shelx_estimated_absorpt_t_max   0.841
_shelx_res_file
;

    15150a.res created by SHELXL-2014/7


TITL 15150a in C2/c
CELL 0.71073 25.6714 3.9034 14.1232 90.000 106.068 90.000
ZERR 8.00 0.0149 0.0023 0.0081 0.000 0.006 0.000
LATT 7
SYMM -x, y, -z+1/2
SFAC C  H  N  O  Br
UNIT 56 32 8 8 8
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 8
ACTA
BOND $H
FMAP 2
PLAN 10
CONF
SIZE 0.030 0.140 0.500
TEMP -100
WGHT    0.050800
FVAR       0.10191
BR1   5    0.298623    0.188263    0.111994    11.00000    0.04573    0.04288 =
         0.03834   -0.00571    0.00499   -0.00124
C1    1    0.416381    0.568258    0.345812    11.00000    0.03412    0.03019 =
         0.04777    0.00063    0.01050    0.00473
C2    1    0.387233    0.481788    0.251966    11.00000    0.03873    0.03069 =
         0.04044    0.00101    0.01609    0.00392
AFIX  43
H2    2    0.400398    0.535047    0.197115    11.00000   -1.20000
AFIX   0
C3    1    0.338920    0.317596    0.239303    11.00000    0.03935    0.02460 =
         0.03698    0.00078    0.00992    0.00342
C4    1    0.319314    0.235587    0.317581    11.00000    0.04448    0.03529 =
         0.04306   -0.00049    0.02164   -0.00085
AFIX  43
H4    2    0.285922    0.116885    0.307615    11.00000   -1.20000
AFIX   0
C5    1    0.348918    0.328576    0.410163    11.00000    0.06457    0.04167 =
         0.03957    0.00496    0.02771    0.00304
AFIX  43
H5    2    0.335559    0.275908    0.464829    11.00000   -1.20000
AFIX   0
C6    1    0.396753    0.493735    0.425511    11.00000    0.05490    0.04267 =
         0.03122    0.00147    0.00535    0.00703
AFIX  43
H6    2    0.416730    0.558124    0.490246    11.00000   -1.20000
AFIX   0
C7    1    0.465910    0.745576    0.359322    11.00000    0.04368    0.04057 =
         0.04422    0.00171    0.00598    0.00761
N1    3    0.505800    0.882495    0.366565    11.00000    0.03598    0.04532 =
         0.03947   -0.00324    0.00495   -0.00235
O1    4    0.548794    1.027846    0.373989    11.00000    0.04555    0.06439 =
         0.05646   -0.00950    0.01131   -0.01696
HKLF 4 1 1 0 0 0 1 0 0 0 1

REM  15150a in C2/c
REM R1 =  0.0434 for     980 Fo > 4sig(Fo)  and  0.0693 for all    1379 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0500      0.0000

REM Highest difference peak  0.726,  deepest hole -0.943,  1-sigma level  0.119
Q1    1   0.2902  0.1784  0.0041  11.00000  0.05    0.73
Q2    1   0.2989 -0.1293  0.1157  11.00000  0.05    0.60
Q3    1   0.3090  0.1503  0.2175  11.00000  0.05    0.55
Q4    1   0.3009  0.4769  0.1161  11.00000  0.05    0.45
Q5    1   0.2407  0.3472  0.0571  11.00000  0.05    0.41
Q6    1   0.3416  0.1751  0.0460  11.00000  0.05    0.37
Q7    1   0.3381  0.1840  0.0704  11.00000  0.05    0.36
Q8    1   0.3159  0.4069  0.2626  11.00000  0.05    0.33
Q9    1   0.3029  0.3006  0.4372  11.00000  0.05    0.33
Q10   1   0.3178 -0.1238  0.2568  11.00000  0.05    0.32
;
_shelx_res_checksum              65040
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Br1 Br 0.29862(2) 0.18826(14) 0.11199(4) 0.0436(2) Uani 1 1 d . .
C1 C 0.41638(19) 0.5683(13) 0.3458(4) 0.0375(12) Uani 1 1 d . .
C2 C 0.38723(19) 0.4818(13) 0.2520(4) 0.0356(11) Uani 1 1 d . .
H2 H 0.4004 0.5350 0.1971 0.043 Uiso 1 1 calc R U
C3 C 0.3389(2) 0.3176(12) 0.2393(4) 0.0338(11) Uani 1 1 d . .
C4 C 0.3193(2) 0.2356(12) 0.3176(4) 0.0390(13) Uani 1 1 d . .
H4 H 0.2859 0.1169 0.3076 0.047 Uiso 1 1 calc R U
C5 C 0.3489(2) 0.3286(14) 0.4102(4) 0.0459(14) Uani 1 1 d . .
H5 H 0.3356 0.2759 0.4648 0.055 Uiso 1 1 calc R U
C6 C 0.3968(2) 0.4937(15) 0.4255(4) 0.0442(13) Uani 1 1 d . .
H6 H 0.4167 0.5581 0.4902 0.053 Uiso 1 1 calc R U
C7 C 0.4659(2) 0.7456(13) 0.3593(4) 0.0441(13) Uani 1 1 d . .
N1 N 0.50580(18) 0.8825(11) 0.3666(3) 0.0414(11) Uani 1 1 d . .
O1 O 0.54879(14) 1.0278(11) 0.3740(3) 0.0560(11) Uani 1 1 d . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0457(3) 0.0429(4) 0.0383(4) -0.0057(2) 0.0050(2) -0.0012(2)
C1 0.034(3) 0.030(3) 0.048(3) 0.001(2) 0.011(2) 0.005(2)
C2 0.039(3) 0.031(3) 0.040(3) 0.001(2) 0.016(2) 0.004(2)
C3 0.039(3) 0.025(2) 0.037(3) 0.001(2) 0.010(2) 0.003(2)
C4 0.044(3) 0.035(3) 0.043(3) 0.000(2) 0.022(3) -0.001(2)
C5 0.065(4) 0.042(3) 0.040(3) 0.005(2) 0.028(3) 0.003(3)
C6 0.055(4) 0.043(3) 0.031(3) 0.001(2) 0.005(3) 0.007(3)
C7 0.044(3) 0.041(4) 0.044(3) 0.002(2) 0.006(3) 0.008(2)
N1 0.036(3) 0.045(3) 0.039(3) -0.003(2) 0.005(2) -0.002(2)
O1 0.046(2) 0.064(3) 0.056(3) -0.010(2) 0.011(2) -0.017(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'
Br Br -0.2901 2.4595 '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
C2 C1 C6 120.6(5)
C2 C1 C7 118.7(5)
C6 C1 C7 120.6(5)
C3 C2 C1 118.4(4)
C3 C2 H2 120.8
C1 C2 H2 120.8
C2 C3 C4 121.8(5)
C2 C3 Br1 119.5(4)
C4 C3 Br1 118.7(4)
C5 C4 C3 118.5(5)
C5 C4 H4 120.7
C3 C4 H4 120.7
C6 C5 C4 121.4(5)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C1 119.3(5)
C5 C6 H6 120.4
C1 C6 H6 120.4
N1 C7 C1 177.2(6)
C7 N1 O1 179.5(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.878(5)
C1 C2 1.372(7)
C1 C6 1.385(7)
C1 C7 1.413(8)
C2 C3 1.363(7)
C2 H2 0.95
C3 C4 1.373(7)
C4 C5 1.367(8)
C4 H4 0.95
C5 C6 1.350(8)
C5 H5 0.95
C6 H6 0.95
C7 N1 1.134(7)
N1 O1 1.219(5)
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
C7 C1 C2 C3 -178.6(5)
C1 C2 C3 Br1 -178.9(4)
Br1 C3 C4 C5 179.7(4)
C7 C1 C6 C5 179.0(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13526713
