#------------------------------------------------------------------------------
#$Date: 2024-04-05 02:05:16 +0200 (Fri 05 de Apr de 2024) $
#$Revision: 291023 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/30/7063063.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_7063063
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         'C16 H8 Br2 N2'
_chemical_formula_sum            'C16 H8 Br2 N2'
_chemical_formula_weight         388.06
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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             2023-04-18T09:17:44-00:00
_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                91.706(5)
_cell_angle_beta                 92.741(5)
_cell_angle_gamma                98.326(5)
_cell_formula_units_Z            2
_cell_length_a                   3.9428(12)
_cell_length_b                   7.726(2)
_cell_length_c                   22.719(7)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.67
_cell_measurement_wavelength     0.71073
_cell_volume                     683.5(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.986
_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      0.060589
_diffrn_orient_matrix_UB_12      0.130101
_diffrn_orient_matrix_UB_13      -0.000917
_diffrn_orient_matrix_UB_21      0.109248
_diffrn_orient_matrix_UB_22      -0.01265
_diffrn_orient_matrix_UB_23      -0.03842
_diffrn_orient_matrix_UB_31      -0.224237
_diffrn_orient_matrix_UB_32      0.007044
_diffrn_orient_matrix_UB_33      -0.021626
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12639
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.796
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.919
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.515
_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    1.886
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.555
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.83
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0471
_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)+6.3416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0
_reflns_number_gt                2220
_reflns_number_total             2747
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj04853e2.cif
_cod_data_source_block           shelx_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7063059--7063065.cif.'
_cod_original_cell_volume        683.5(4)
_cod_database_code               7063063
_shelx_estimated_absorpt_t_min   0.138
_shelx_estimated_absorpt_t_max   0.861
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.7932(14) 0.3862(8) 0.8282(3) 0.0188(12) Uani 1 1 d . . . . .
C2 C 0.6699(14) 0.2166(8) 0.8467(2) 0.0174(12) Uani 1 1 d . . . . .
C3 C 0.7697(15) 0.1648(8) 0.9035(3) 0.0205(13) Uani 1 1 d . . . . .
C4 C 0.9832(15) 0.2797(9) 0.9415(3) 0.0235(13) Uani 1 1 d . . . . .
H4 H 1.051283 0.244047 0.979437 0.028 Uiso 1 1 calc R U . . .
C5 C 1.0975(15) 0.4484(9) 0.9238(3) 0.0238(13) Uani 1 1 d . . . . .
H5 H 1.240878 0.528435 0.950046 0.029 Uiso 1 1 calc R U . . .
C6 C 1.0045(15) 0.5003(8) 0.8683(3) 0.0219(13) Uani 1 1 d . . . . .
H6 H 1.085494 0.615885 0.85713 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4259(15) 0.0952(8) 0.8111(3) 0.0193(12) Uani 1 1 d . . . . .
C8 C 0.6424(17) -0.0087(9) 0.9212(3) 0.0264(14) Uani 1 1 d . . . . .
C9 C 0.6972(14) 0.4443(8) 0.7688(2) 0.0175(12) Uani 1 1 d . . . . .
C10 C 0.6159(15) 0.6115(8) 0.7631(2) 0.0200(12) Uani 1 1 d . . . . .
H10 H 0.625492 0.686691 0.797203 0.024 Uiso 1 1 calc R U . . .
C11 C 0.5202(16) 0.6719(8) 0.7085(3) 0.0225(13) Uani 1 1 d . . . . .
H11 H 0.461136 0.786489 0.705882 0.027 Uiso 1 1 calc R U . . .
C12 C 0.5105(14) 0.5655(8) 0.6578(2) 0.0174(12) Uani 1 1 d . . . . .
C13 C 0.6063(15) 0.3995(8) 0.6637(2) 0.0191(12) Uani 1 1 d . . . . .
H13 H 0.607471 0.325546 0.629545 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6998(15) 0.3403(8) 0.7183(2) 0.0200(12) Uani 1 1 d . . . . .
H14 H 0.766236 0.227311 0.721051 0.024 Uiso 1 1 calc R U . . .
C15 C 0.4062(15) 0.6121(8) 0.5979(3) 0.0193(12) Uani 1 1 d . . . . .
H15 H 0.431131 0.526687 0.568095 0.023 Uiso 1 1 calc R U . . .
C16 C 0.2824(14) 0.7531(8) 0.5779(2) 0.0180(12) Uani 1 1 d . . . . .
Br1 Br 0.19625(17) 0.95051(8) 0.62137(3) 0.02607(18) Uani 1 1 d . . . . .
Br2 Br 0.16569(16) 0.76504(9) 0.49655(3) 0.02722(19) Uani 1 1 d . . . . .
N1 N 0.2237(14) -0.0032(8) 0.7861(2) 0.0299(13) Uani 1 1 d . . . . .
N2 N 0.5431(16) -0.1457(8) 0.9358(3) 0.0380(15) 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
C6 C1 C2 117.9(5) . . ?
C6 C1 C9 120.7(5) . . ?
C2 C1 C9 121.4(5) . . ?
C3 C2 C1 119.9(5) . . ?
C3 C2 C7 117.7(5) . . ?
C1 C2 C7 122.3(5) . . ?
C4 C3 C2 120.6(6) . . ?
C4 C3 C8 120.5(5) . . ?
C2 C3 C8 118.9(6) . . ?
C3 C4 C5 119.4(5) . . ?
C6 C5 C4 120.7(6) . . ?
C5 C6 C1 121.5(6) . . ?
N1 C7 C2 175.8(6) . . ?
N2 C8 C3 179.3(7) . . ?
C14 C9 C10 118.4(5) . . ?
C14 C9 C1 122.5(5) . . ?
C10 C9 C1 119.0(5) . . ?
C9 C10 C11 121.4(5) . . ?
C10 C11 C12 120.4(6) . . ?
C11 C12 C13 117.7(5) . . ?
C11 C12 C15 125.7(5) . . ?
C13 C12 C15 116.6(5) . . ?
C14 C13 C12 121.4(5) . . ?
C9 C14 C13 120.6(5) . . ?
C16 C15 C12 131.6(6) . . ?
C15 C16 Br1 128.0(4) . . ?
C15 C16 Br2 119.6(5) . . ?
Br1 C16 Br2 112.4(3) . . ?
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 C6 1.403(9) . ?
C1 C2 1.414(8) . ?
C1 C9 1.485(7) . ?
C2 C3 1.416(7) . ?
C2 C7 1.442(9) . ?
C3 C4 1.383(9) . ?
C3 C8 1.437(9) . ?
C4 C5 1.394(9) . ?
C5 C6 1.383(8) . ?
C7 N1 1.136(8) . ?
C8 N2 1.139(9) . ?
C9 C14 1.382(8) . ?
C9 C10 1.383(8) . ?
C10 C11 1.393(8) . ?
C11 C12 1.391(8) . ?
C12 C13 1.397(8) . ?
C12 C15 1.472(7) . ?
C13 C14 1.387(8) . ?
C15 C16 1.340(8) . ?
C16 Br1 1.873(6) . ?
C16 Br2 1.891(5) . ?
