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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232108.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_7232108
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 H3 Cl2 N O'
_chemical_formula_weight         188.00
_chemical_melting_point          349.0(10)
_chemical_name_common            '2,6-dichlorobenzonitrile oxide'
_chemical_name_systematic        2,6-dichlorobenzonitrile-N-oxide
_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
_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                 97.848(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9611(2)
_cell_length_b                   13.3377(5)
_cell_length_c                   14.4800(5)
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.50
_cell_measurement_theta_min      3.08
_cell_volume                     757.84(5)
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker-AXS D8 Venture PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6061
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.487
_diffrn_reflns_theta_min         4.527
_diffrn_source                   'ImuS micro-focus'
_exptl_absorpt_coefficient_mu    7.172
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014 (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_transmission_factor_max   0.7538
_exptl_transmission_factor_min   0.4212
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0368
_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)+(0.0499P)²+0.5840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1416
_reflns_number_total             1535
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce02008f2.cif
_cod_data_source_block           15145b26diCl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '348-350K' was changed to '349.0(10)'
- 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_database_code               7232108
_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   0.267
_shelx_estimated_absorpt_t_max   0.301
_shelx_res_file
;

    15145b.res created by SHELXL-2014/7


TITL 15145a in P2(1)/c
CELL 1.54178 3.9611 13.3377 14.4800 90.000 97.848 90.000
ZERR 4.00 0.0002 0.0005 0.0005 0.000 0.002 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C  H  N  O  Cl
UNIT 28 12 4 4 8
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 5
CONF
SIZE 0.220 0.230 0.250
TEMP -150.150
WGHT    0.049900    0.584000
FVAR       0.17810
CL1   5    0.868124    0.400631    0.799651    11.00000    0.04027    0.03296 =
         0.01485   -0.00750    0.00397    0.00249
CL2   5    0.725974    0.101945    0.546400    11.00000    0.03412    0.01555 =
         0.03184   -0.00542    0.00280   -0.00317
C1    1    0.813538    0.257316    0.666640    11.00000    0.01357    0.01834 =
         0.01525    0.00519    0.00027    0.00362
C2    1    0.925118    0.354887    0.691146    11.00000    0.01851    0.01983 =
         0.01258   -0.00171   -0.00163    0.00374
C3    1    1.078256    0.414008    0.630741    11.00000    0.02161    0.01389 =
         0.02311   -0.00048    0.00021    0.00015
AFIX  43
H3    2    1.153068    0.479811    0.648354    11.00000   -1.20000
AFIX   0
C4    1    1.121772    0.376189    0.543862    11.00000    0.01943    0.01781 =
         0.01942    0.00612    0.00414    0.00231
AFIX  43
H4    2    1.227206    0.416732    0.502046    11.00000   -1.20000
AFIX   0
C5    1    1.014219    0.280324    0.516953    11.00000    0.02012    0.02018 =
         0.01383   -0.00041    0.00224    0.00575
AFIX  43
H5    2    1.044733    0.255278    0.457235    11.00000   -1.20000
AFIX   0
C6    1    0.861614    0.221639    0.578475    11.00000    0.01734    0.01385 =
         0.01689   -0.00082   -0.00161    0.00347
C7    1    0.650933    0.197589    0.729082    11.00000    0.02045    0.02277 =
         0.02119    0.00642    0.00287    0.00347
N1    3    0.517006    0.159211    0.784799    11.00000    0.02075    0.01812 =
         0.01908    0.00134    0.00437    0.00192
O1    4    0.373671    0.116398    0.843532    11.00000    0.03512    0.03254 =
         0.02837    0.01016    0.01636   -0.00049
HKLF 4 1 1 0 0 0 1 0 0 0 1

REM  15145a in P2(1)/c
REM R1 =  0.0368 for    1416 Fo > 4sig(Fo)  and  0.0396 for all    1535 data
REM    100 parameters refined using      0 restraints

END

WGHT      0.0499      0.5840

REM Highest difference peak  0.290,  deepest hole -0.460,  1-sigma level  0.077
Q1    1   1.0310  0.2402  0.5606  11.00000  0.05    0.29
Q2    1   0.9177  0.3002  0.6817  11.00000  0.05    0.29
Q3    1   0.8699  0.2616  0.5402  11.00000  0.05    0.27
Q4    1   0.9076  0.3836  0.6427  11.00000  0.05    0.26
Q5    1   0.8816  0.2377  0.6304  11.00000  0.05    0.24
;
_shelx_res_checksum              82760
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_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
Cl1 Cl 0.86812(15) 0.40063(4) 0.79965(3) 0.02934(18) Uani 1 1 d . .
Cl2 Cl 0.72597(14) 0.10194(3) 0.54640(4) 0.02733(18) Uani 1 1 d . .
C1 C 0.8135(5) 0.25732(14) 0.66664(12) 0.0159(4) Uani 1 1 d . .
C2 C 0.9251(5) 0.35489(14) 0.69115(12) 0.0173(4) Uani 1 1 d . .
C3 C 1.0783(5) 0.41401(14) 0.63074(14) 0.0198(4) Uani 1 1 d . .
H3 H 1.1531 0.4798 0.6484 0.024 Uiso 1 1 calc R U
C4 C 1.1218(5) 0.37619(14) 0.54386(14) 0.0187(4) Uani 1 1 d . .
H4 H 1.2272 0.4167 0.5020 0.022 Uiso 1 1 calc R U
C5 C 1.0142(5) 0.28032(14) 0.51695(12) 0.0181(4) Uani 1 1 d . .
H5 H 1.0447 0.2553 0.4572 0.022 Uiso 1 1 calc R U
C6 C 0.8616(5) 0.22164(13) 0.57847(12) 0.0164(4) Uani 1 1 d . .
C7 C 0.6509(5) 0.19759(15) 0.72908(14) 0.0215(4) Uani 1 1 d . .
N1 N 0.5170(4) 0.15921(12) 0.78480(11) 0.0192(4) Uani 1 1 d . .
O1 O 0.3737(4) 0.11640(12) 0.84353(11) 0.0309(4) 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
Cl1 0.0403(3) 0.0330(3) 0.0148(3) -0.00750(17) 0.0040(2) 0.0025(2)
Cl2 0.0341(3) 0.0156(3) 0.0318(3) -0.00542(17) 0.0028(2) -0.00317(17)
C1 0.0136(9) 0.0183(9) 0.0153(8) 0.0052(7) 0.0003(7) 0.0036(7)
C2 0.0185(9) 0.0198(9) 0.0126(8) -0.0017(7) -0.0016(7) 0.0037(7)
C3 0.0216(10) 0.0139(8) 0.0231(10) -0.0005(7) 0.0002(7) 0.0001(7)
C4 0.0194(10) 0.0178(9) 0.0194(9) 0.0061(7) 0.0041(7) 0.0023(7)
C5 0.0201(9) 0.0202(9) 0.0138(8) -0.0004(7) 0.0022(7) 0.0058(7)
C6 0.0173(9) 0.0139(8) 0.0169(9) -0.0008(7) -0.0016(7) 0.0035(7)
C7 0.0204(10) 0.0228(9) 0.0212(9) 0.0064(8) 0.0029(8) 0.0035(7)
N1 0.0207(8) 0.0181(8) 0.0191(8) 0.0013(6) 0.0044(6) 0.0019(6)
O1 0.0351(9) 0.0325(8) 0.0284(8) 0.0102(6) 0.0164(7) -0.0005(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C6 C1 C2 117.92(17)
C6 C1 C7 121.26(17)
C2 C1 C7 120.81(17)
C3 C2 C1 121.36(17)
C3 C2 Cl1 119.88(15)
C1 C2 Cl1 118.75(15)
C2 C3 C4 119.16(17)
C2 C3 H3 120.4
C4 C3 H3 120.4
C5 C4 C3 121.23(18)
C5 C4 H4 119.4
C3 C4 H4 119.4
C6 C5 C4 118.99(17)
C6 C5 H5 120.5
C4 C5 H5 120.5
C5 C6 C1 121.34(17)
C5 C6 Cl2 119.75(14)
C1 C6 Cl2 118.90(14)
N1 C7 C1 172.3(2)
C7 N1 O1 178.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.7288(18)
Cl2 C6 1.7277(19)
C1 C6 1.400(3)
C1 C2 1.404(3)
C1 C7 1.423(3)
C2 C3 1.378(3)
C3 C4 1.388(3)
C3 H3 0.95
C4 C5 1.387(3)
C4 H4 0.95
C5 C6 1.385(3)
C5 H5 0.95
C7 N1 1.145(3)
N1 O1 1.226(2)
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 -179.01(18)
C6 C1 C2 Cl1 179.94(14)
C7 C1 C2 Cl1 1.1(2)
Cl1 C2 C3 C4 -179.94(15)
C4 C5 C6 Cl2 -179.96(14)
C7 C1 C6 C5 178.81(17)
C2 C1 C6 Cl2 -179.87(13)
C7 C1 C6 Cl2 -1.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 76185
