Intramolecular geometry and intermolecular interactions of the CNO group of crystalline benzonitrile oxides: a comparison with phenyl cyanates, phenyl isocyanates, and phenyl azides
Dhami, Jaya K.; Idzorek, Kiersten M.; Johnson, Ryan B.; Van Auken, Kaitlyn S.; Ojala, William H.; CrystEngComm 21 (2019) 908–; doi:10.1039/C8CE02008F

data_7232108
_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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0499P)^2^+0.5840P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.267
_shelx_estimated_absorpt_t_max   0.301
_shelx_res_checksum              82760