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_7232109
_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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0508P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.154
_shelx_estimated_absorpt_t_max   0.841
_shelx_res_checksum              65040