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#$Date: 2024-04-05 03:05:16 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291023 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/30/7063061.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_7063061
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 O'
_chemical_formula_sum            'C16 H8 Br2 N2 O'
_chemical_formula_weight         404.06
_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             2023-03-31T15:46:18-00:00
_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                 96.755(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5579(18)
_cell_length_b                   8.9875(15)
_cell_length_c                   15.356(3)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.22
_cell_measurement_wavelength     0.71073
_cell_volume                     1447.0(4)
_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 0.992
_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      -0.088882
_diffrn_orient_matrix_UB_12      0.004856
_diffrn_orient_matrix_UB_13      -0.03042
_diffrn_orient_matrix_UB_21      0.032091
_diffrn_orient_matrix_UB_22      -0.026974
_diffrn_orient_matrix_UB_23      -0.056584
_diffrn_orient_matrix_UB_31      -0.012044
_diffrn_orient_matrix_UB_32      -0.107702
_diffrn_orient_matrix_UB_33      0.0128
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15199
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.426
_diffrn_reflns_theta_min         1.942
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.601
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.588
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0409P)²+1.3635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0
_reflns_number_gt                2295
_reflns_number_total             2957
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj04853e2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7063059--7063065.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7063061
_shelx_estimated_absorpt_t_min   0.207
_shelx_estimated_absorpt_t_max   0.663
_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 0.4177(3) 0.5838(4) 0.6831(2) 0.0143(7) Uani 1 1 d . . . . .
C2 C 0.4657(3) 0.4726(4) 0.6346(2) 0.0140(7) Uani 1 1 d . . . . .
H2 H 0.553886 0.448274 0.643014 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3824(3) 0.3968(4) 0.5731(2) 0.0107(7) Uani 1 1 d . . . . .
C4 C 0.2521(3) 0.4321(4) 0.5615(2) 0.0130(7) Uani 1 1 d . . . . .
C5 C 0.2068(3) 0.5460(4) 0.6110(2) 0.0176(8) Uani 1 1 d . . . . .
H5 H 0.118952 0.571601 0.603133 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2899(3) 0.6212(4) 0.6713(2) 0.0163(8) Uani 1 1 d . . . . .
H6 H 0.25927 0.69916 0.704952 0.02 Uiso 1 1 calc R U . . .
C7 C 0.4289(3) 0.2835(4) 0.5189(2) 0.0133(7) Uani 1 1 d . . . . .
C8 C 0.1638(3) 0.3496(4) 0.5006(2) 0.0168(8) Uani 1 1 d . . . . .
C9 C 0.6191(3) 0.6348(4) 0.7679(2) 0.0165(8) Uani 1 1 d . . . . .
C10 C 0.7088(3) 0.7162(4) 0.7302(2) 0.0182(8) Uani 1 1 d . . . . .
H10 H 0.683267 0.784666 0.684278 0.022 Uiso 1 1 calc R U . . .
C11 C 0.8370(3) 0.6967(4) 0.7602(2) 0.0168(8) Uani 1 1 d . . . . .
H11 H 0.899516 0.753032 0.734914 0.02 Uiso 1 1 calc R U . . .
C12 C 0.8750(3) 0.5951(4) 0.8271(2) 0.0127(7) Uani 1 1 d . . . . .
C13 C 0.7811(3) 0.5128(4) 0.8614(2) 0.0185(8) Uani 1 1 d . . . . .
H13 H 0.805432 0.44092 0.905551 0.022 Uiso 1 1 calc R U . . .
C14 C 0.6535(3) 0.5325(4) 0.8329(2) 0.0186(8) Uani 1 1 d . . . . .
H14 H 0.590407 0.476376 0.857657 0.022 Uiso 1 1 calc R U . . .
C15 C 1.0085(3) 0.5650(4) 0.8605(2) 0.0155(8) Uani 1 1 d . . . . .
H15 H 1.025514 0.465677 0.879574 0.019 Uiso 1 1 calc R U . . .
C16 C 1.1083(3) 0.6534(4) 0.8683(2) 0.0159(8) Uani 1 1 d . . . . .
Br1 Br 1.10957(4) 0.85785(4) 0.84292(3) 0.02556(13) Uani 1 1 d . . . . .
Br2 Br 1.27163(3) 0.58222(5) 0.91234(3) 0.02695(14) Uani 1 1 d . . . . .
N1 N 0.4636(3) 0.1957(4) 0.4739(2) 0.0218(7) Uani 1 1 d . . . . .
N2 N 0.0927(3) 0.2874(4) 0.4527(2) 0.0227(7) Uani 1 1 d . . . . .
O1 O 0.4899(2) 0.6679(3) 0.74475(18) 0.0229(6) 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'
O O 0.0106 0.006 '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
O1 C1 C2 124.2(3) . . ?
O1 C1 C6 114.3(3) . . ?
C2 C1 C6 121.4(3) . . ?
C1 C2 C3 118.6(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 C7 120.5(3) . . ?
C4 C3 C7 118.9(3) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 C8 119.6(3) . . ?
C3 C4 C8 120.9(3) . . ?
C6 C5 C4 119.7(3) . . ?
C5 C6 C1 120.3(3) . . ?
N1 C7 C3 178.0(4) . . ?
N2 C8 C4 178.5(4) . . ?
C14 C9 C10 121.7(3) . . ?
C14 C9 O1 119.5(3) . . ?
C10 C9 O1 118.5(3) . . ?
C9 C10 C11 119.0(3) . . ?
C10 C11 C12 120.7(3) . . ?
C13 C12 C11 118.0(3) . . ?
C13 C12 C15 118.0(3) . . ?
C11 C12 C15 124.0(3) . . ?
C14 C13 C12 121.7(3) . . ?
C9 C14 C13 118.8(3) . . ?
C16 C15 C12 130.4(3) . . ?
C15 C16 Br1 126.7(3) . . ?
C15 C16 Br2 121.1(3) . . ?
Br1 C16 Br2 112.16(18) . . ?
C1 O1 C9 120.3(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 O1 1.371(4) . ?
C1 C2 1.378(5) . ?
C1 C6 1.381(5) . ?
C2 C3 1.392(5) . ?
C3 C4 1.402(5) . ?
C3 C7 1.438(5) . ?
C4 C5 1.392(5) . ?
C4 C8 1.445(5) . ?
C5 C6 1.376(5) . ?
C7 N1 1.137(4) . ?
C8 N2 1.135(5) . ?
C9 C14 1.373(5) . ?
C9 C10 1.377(5) . ?
C9 O1 1.401(4) . ?
C10 C11 1.389(5) . ?
C11 C12 1.399(5) . ?
C12 C13 1.389(5) . ?
C12 C15 1.467(5) . ?
C13 C14 1.378(5) . ?
C15 C16 1.314(5) . ?
C16 Br1 1.879(4) . ?
C16 Br2 1.888(3) . ?
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
O1 C1 C2 C3 -179.1(3) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C1 C2 C3 C7 177.9(3) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C7 C3 C4 C5 -177.3(3) . . . . ?
C2 C3 C4 C8 -177.2(3) . . . . ?
C7 C3 C4 C8 4.3(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C8 C4 C5 C6 177.7(3) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
O1 C1 C6 C5 179.6(3) . . . . ?
C2 C1 C6 C5 0.9(6) . . . . ?
C14 C9 C10 C11 -1.6(5) . . . . ?
O1 C9 C10 C11 172.5(3) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 1.2(5) . . . . ?
C10 C11 C12 C15 178.1(3) . . . . ?
C11 C12 C13 C14 -2.0(5) . . . . ?
C15 C12 C13 C14 -179.1(3) . . . . ?
C10 C9 C14 C13 0.8(5) . . . . ?
O1 C9 C14 C13 -173.2(3) . . . . ?
C12 C13 C14 C9 1.0(5) . . . . ?
C13 C12 C15 C16 -150.3(4) . . . . ?
C11 C12 C15 C16 32.8(6) . . . . ?
C12 C15 C16 Br1 3.3(6) . . . . ?
C12 C15 C16 Br2 -178.9(3) . . . . ?
C2 C1 O1 C9 -5.9(5) . . . . ?
C6 C1 O1 C9 175.3(3) . . . . ?
C14 C9 O1 C1 -87.0(4) . . . . ?
C10 C9 O1 C1 98.7(4) . . . . ?
