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_7063064
_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         'C24 H10 Br2 N4 O2'
_chemical_formula_sum            'C24 H10 Br2 N4 O2'
_chemical_formula_weight         546.18
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_audit_update_record
;
2023-09-11 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   15.480(7)
_cell_length_c                   22.251(10)
_cell_measurement_reflns_used    7454
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.25
_cell_measurement_wavelength     0.71073
_cell_volume                     2111.5(17)
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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      -0.026762
_diffrn_orient_matrix_UB_12      -0.008804
_diffrn_orient_matrix_UB_13      -0.043907
_diffrn_orient_matrix_UB_21      0.058673
_diffrn_orient_matrix_UB_22      0.059044
_diffrn_orient_matrix_UB_23      -0.008444
_diffrn_orient_matrix_UB_31      0.149846
_diffrn_orient_matrix_UB_32      -0.024691
_diffrn_orient_matrix_UB_33      -0.004536
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_unetI/netI     0.0991
_diffrn_reflns_Laue_measured_fraction_full 0.984
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_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
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_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8688
_diffrn_reflns_point_group_measured_fraction_full 0.969
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_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.368
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_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.87
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_exptl_absorpt_process_details
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.924
_refine_diff_density_min         -1.303
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.057(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0822P)^2^+2.7592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.159
_refine_ls_wR_factor_ref         0.1711
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                2946
_reflns_number_total             4147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04853e2.cif
_cod_data_source_block           shelx_CCDC5
_cod_depositor_comments
'Adding full bibliography for 7063059--7063065.cif.'
_cod_original_cell_volume        2111.4(16)
_cod_database_code               7063064
_shelx_estimated_absorpt_t_min   0.293
_shelx_estimated_absorpt_t_max   0.631
_shelx_shelxl_version_number     2018/3