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_7232111
_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            'C3.5 H2 Cl0.5 N0.5 O0.5'
_chemical_formula_weight         76.78
_chemical_melting_point          354.5(15)
_chemical_name_common            '4-chlorobenzonitrile oxide'
_chemical_name_systematic        4-chlorobenzonitrile-N-oxide
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 101.2010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.5995(4)
_cell_length_b                   7.7964(7)
_cell_length_c                   9.3711(8)
_cell_measurement_reflns_used    643
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      3.43
_cell_volume                     329.64(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'
_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 0.998
_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  0.0152
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.343
_diffrn_reflns_theta_min         2.215
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       needle
_exptl_crystal_F_000             156
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   0.7455
_exptl_transmission_factor_min   0.6579
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0244
_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^)+(0.0341P)^2^+0.0940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0698
_reflns_Friedel_coverage         0.000
_reflns_number_gt                740
_reflns_number_total             792
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02008f2.cif
_cod_data_source_block           14141z4Cl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '353-356 K' was changed to
'354.5(15)' - 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_formula_sum        'C3.50 H2 Cl0.50 N0.50 O0.50'
_cod_database_code               7232111
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.6579
_shelx_estimated_absorpt_t_max   0.7455
_shelx_res_checksum              28104