gem-Dibromovinyl phthalonitriles: synthesis, structure elucidation, Hirshfeld surface analysis and energy framework calculations
Ali, Hasrat; van Lier, Johan E.; New Journal of Chemistry 48 (2024) 6350–6366; doi:10.1039/D3NJ04853E

data_7063060
_publ_section_title
;
 gem-Dibromovinyl phthalonitriles: synthesis, structure elucidation,
 Hirshfeld surface analysis and energy framework calculations
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6350
_journal_page_last               6366
_journal_paper_doi               10.1039/D3NJ04853E
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H8 Br2 N2'
_chemical_formula_sum            'C16 H8 Br2 N2'
_chemical_formula_weight         388.06
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2023-10-11T10:48:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-10-17 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.710(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.792(3)
_cell_length_b                   12.009(2)
_cell_length_c                   8.5544(16)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.27
_cell_measurement_wavelength     0.71073
_cell_volume                     1392.2(5)
_computing_cell_refinement       'SAINT V8.38A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      0.001748
_diffrn_orient_matrix_UB_12      -0.010218
_diffrn_orient_matrix_UB_13      0.116505
_diffrn_orient_matrix_UB_21      0.069042
_diffrn_orient_matrix_UB_22      0.029337
_diffrn_orient_matrix_UB_23      0.023169
_diffrn_orient_matrix_UB_31      -0.025985
_diffrn_orient_matrix_UB_32      0.07726
_diffrn_orient_matrix_UB_33      0.006611
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13281
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.444
_diffrn_reflns_theta_min         2.266
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.812
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0216
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0064P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0392
_refine_ls_wR_factor_ref         0.0404
_reflns_Friedel_coverage         0.985
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2619
_reflns_number_total             2851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04853e2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7063059--7063065.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7063060
_shelx_estimated_absorpt_t_min   0.389
_shelx_estimated_absorpt_t_max   0.594
_shelx_shelxl_version_number     2018/3