#------------------------------------------------------------------------------
#$Date: 2024-04-05 03:05:16 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291023 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/30/7063062.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7063062
loop_
_publ_author_name
'Ali, Hasrat'
'van Lier, Johan E.'
_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_formula_moiety         'C18 H8 Br2 N2'
_chemical_formula_sum            'C18 H8 Br2 N2'
_chemical_formula_weight         412.08
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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             2023-04-04T09:59:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-09-11 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.726(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.686(3)
_cell_length_b                   16.072(4)
_cell_length_c                   8.999(2)
_cell_measurement_reflns_used    7536
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.26
_cell_measurement_wavelength     0.71073
_cell_volume                     1544.8(7)
_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      296(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      -0.03112
_diffrn_orient_matrix_UB_12      -0.004472
_diffrn_orient_matrix_UB_13      0.088718
_diffrn_orient_matrix_UB_21      -0.106529
_diffrn_orient_matrix_UB_22      -0.001822
_diffrn_orient_matrix_UB_23      -0.029112
_diffrn_orient_matrix_UB_31      0.005377
_diffrn_orient_matrix_UB_32      -0.061981
_diffrn_orient_matrix_UB_33      -0.005545
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.077
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10361
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         1.907
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.243
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.522
_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    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.98
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.98
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0230P)²+0.0865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.07
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         0
_reflns_number_gt                1848
_reflns_number_total             3122
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj04853e2.cif
_cod_data_source_block           shelx_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7063059--7063065.cif.'
_cod_original_cell_volume        1544.9(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7063062
_shelx_estimated_absorpt_t_min   0.264
_shelx_estimated_absorpt_t_max   0.859
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5230(4) 0.6656(3) 0.2651(5) 0.0253(12) Uani 1 1 d . . . . .
C2 C 0.4423(4) 0.6215(3) 0.1701(5) 0.0214(11) Uani 1 1 d . . . . .
C3 C 0.3588(4) 0.6633(3) 0.0749(5) 0.0231(11) Uani 1 1 d . . . . .
C4 C 0.3559(4) 0.7495(3) 0.0742(5) 0.0264(11) Uani 1 1 d . . . . .
H4 H 0.299247 0.777468 0.011735 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4364(4) 0.7934(3) 0.1654(5) 0.0263(12) Uani 1 1 d . . . . .
H5 H 0.435539 0.851286 0.162894 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5187(4) 0.7528(3) 0.2609(5) 0.0283(12) Uani 1 1 d . . . . .
H6 H 0.572035 0.783509 0.323386 0.034 Uiso 1 1 calc R U . . .
C7 C 0.6103(5) 0.6226(3) 0.3629(5) 0.0302(13) Uani 1 1 d . . . . .
C8 C 0.6814(5) 0.5845(3) 0.4418(5) 0.0263(11) Uani 1 1 d . . . . .
C9 C 0.7680(4) 0.5388(3) 0.5329(5) 0.0256(12) Uani 1 1 d . . . . .
C10 C 0.8106(5) 0.5694(3) 0.6687(5) 0.0274(12) Uani 1 1 d . . . . .
H10 H 0.780121 0.619946 0.70257 0.033 Uiso 1 1 calc R U . . .
C11 C 0.8969(4) 0.5264(3) 0.7546(5) 0.0259(12) Uani 1 1 d . . . . .
H11 H 0.925404 0.548638 0.844847 0.031 Uiso 1 1 calc R U . . .
C12 C 0.9421(4) 0.4501(3) 0.7079(5) 0.0243(12) Uani 1 1 d . . . . .
C13 C 0.9008(4) 0.4197(3) 0.5718(5) 0.0252(12) Uani 1 1 d . . . . .
H13 H 0.931809 0.369229 0.538137 0.03 Uiso 1 1 calc R U . . .
C14 C 0.8151(5) 0.4625(3) 0.4852(5) 0.0302(13) Uani 1 1 d . . . . .
H14 H 0.788016 0.440613 0.394122 0.036 Uiso 1 1 calc R U . . .
C15 C 1.0397(4) 0.4087(3) 0.8017(5) 0.0246(12) Uani 1 1 d . . . . .
H15 H 1.098454 0.443804 0.847262 0.03 Uiso 1 1 calc R U . . .
C16 C 1.0544(4) 0.3286(3) 0.8291(5) 0.0270(12) Uani 1 1 d . . . . .
C17 C 0.4468(4) 0.5320(3) 0.1683(5) 0.0280(12) Uani 1 1 d . . . . .
C18 C 0.2728(5) 0.6183(3) -0.0221(5) 0.0262(12) Uani 1 1 d . . . . .
Br1 Br 1.18923(6) 0.29055(3) 0.95118(6) 0.04110(18) Uani 1 1 d . . . . .
Br2 Br 0.94857(5) 0.24285(3) 0.75948(6) 0.03573(17) Uani 1 1 d . . . . .
N1 N 0.4514(4) 0.4608(3) 0.1657(5) 0.0392(12) Uani 1 1 d . . . . .
N2 N 0.2041(4) 0.5842(3) -0.0994(5) 0.0413(12) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.2(4) . . ?
C2 C1 C7 120.7(4) . . ?
C6 C1 C7 121.1(4) . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 C17 119.7(4) . . ?
C3 C2 C17 119.8(4) . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 C18 119.0(4) . . ?
C2 C3 C18 121.0(4) . . ?
C5 C4 C3 120.0(4) . . ?
C4 C5 C6 120.6(4) . . ?
C5 C6 C1 120.7(4) . . ?
C8 C7 C1 177.9(5) . . ?
C7 C8 C9 178.6(6) . . ?
C10 C9 C14 118.1(4) . . ?
C10 C9 C8 121.2(4) . . ?
C14 C9 C8 120.7(4) . . ?
C11 C10 C9 121.2(4) . . ?
C10 C11 C12 120.5(4) . . ?
C11 C12 C13 118.6(4) . . ?
C11 C12 C15 118.1(4) . . ?
C13 C12 C15 123.2(4) . . ?
C14 C13 C12 121.2(4) . . ?
C13 C14 C9 120.4(4) . . ?
C16 C15 C12 128.6(4) . . ?
C15 C16 Br2 125.9(4) . . ?
C15 C16 Br1 120.7(4) . . ?
Br2 C16 Br1 113.4(2) . . ?
N1 C17 C2 179.1(6) . . ?
N2 C18 C3 178.7(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.391(6) . ?
C1 C6 1.404(6) . ?
C1 C7 1.440(6) . ?
C2 C3 1.391(6) . ?
C2 C17 1.439(6) . ?
C3 C4 1.386(6) . ?
C3 C18 1.443(6) . ?
C4 C5 1.367(6) . ?
C5 C6 1.375(6) . ?
C7 C8 1.192(6) . ?
C8 C9 1.423(6) . ?
C9 C10 1.381(6) . ?
C9 C14 1.399(6) . ?
C10 C11 1.372(6) . ?
C11 C12 1.388(6) . ?
C12 C13 1.379(6) . ?
C12 C15 1.480(6) . ?
C13 C14 1.370(6) . ?
C15 C16 1.319(6) . ?
C16 Br2 1.879(5) . ?
C16 Br1 1.887(5) . ?
C17 N1 1.145(5) . ?
C18 N2 1.137(6) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.7(7) . . . . ?
C7 C1 C2 C3 -179.5(5) . . . . ?
C6 C1 C2 C17 178.2(4) . . . . ?
C7 C1 C2 C17 -0.6(7) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
C17 C2 C3 C4 -178.8(4) . . . . ?
C1 C2 C3 C18 -178.7(4) . . . . ?
C17 C2 C3 C18 2.3(7) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C18 C3 C4 C5 179.9(5) . . . . ?
C3 C4 C5 C6 -1.5(7) . . . . ?
C4 C5 C6 C1 1.0(7) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
C7 C1 C6 C5 178.9(5) . . . . ?
C14 C9 C10 C11 0.3(7) . . . . ?
C8 C9 C10 C11 -178.1(5) . . . . ?
C9 C10 C11 C12 -1.2(8) . . . . ?
C10 C11 C12 C13 1.7(7) . . . . ?
C10 C11 C12 C15 177.0(4) . . . . ?
C11 C12 C13 C14 -1.4(7) . . . . ?
C15 C12 C13 C14 -176.5(5) . . . . ?
C12 C13 C14 C9 0.5(8) . . . . ?
C10 C9 C14 C13 0.1(7) . . . . ?
C8 C9 C14 C13 178.4(5) . . . . ?
C11 C12 C15 C16 143.2(5) . . . . ?
C13 C12 C15 C16 -41.7(8) . . . . ?
C12 C15 C16 Br2 -2.3(8) . . . . ?
C12 C15 C16 Br1 179.0(4) . . . . ?
