#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/30/7123069.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_7123069
loop_
_publ_author_name
'Liu, Jun'
'Min, Yang'
'Dou, Chuandong'
'Tian, Hongkun'
'Wang, Lixiang'
_publ_section_title
;
 A Disk-Type Polyarene Containing Four B← N Units
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00769E
_journal_year                    2019
_chemical_formula_moiety         'C20 H8 Br4 N4'
_chemical_formula_sum            'C20 H8 Br4 N4'
_chemical_formula_weight         623.94
_chemical_name_systematic        TBNP
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-12-29 deposited with the CCDC.    2019-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.727(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3870(9)
_cell_length_b                   15.2414(18)
_cell_length_c                   17.567(2)
_cell_measurement_reflns_used    3002
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.35
_cell_volume                     1954.9(4)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_min         1.778
_exptl_absorpt_coefficient_mu    8.249
_exptl_absorpt_correction_T_max  0.176925
_exptl_absorpt_correction_T_min  0.146238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0931 before and 0.0224 after correction.
The Ratio of minimum to maximum transmission is 0.5373.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.120
_exptl_crystal_description       cube
_exptl_crystal_F_000             1184
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3 and CH3OH'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2822
_reflns_number_total             3979
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc00769e2.cif
_cod_data_source_block           2
_cod_database_code               7123069
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.276
_shelx_estimated_absorpt_t_min   0.232
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br4 Br 0.20967(7) 0.31560(3) 0.13829(3) 0.05805(17) Uani 1 1 d .
Br1 Br 0.08819(7) 0.18592(3) 0.54160(3) 0.05592(17) Uani 1 1 d .
Br2 Br 0.30280(7) 0.05157(3) 0.46014(3) 0.05119(16) Uani 1 1 d .
Br3 Br 0.00538(8) 0.45156(4) 0.22391(3) 0.06634(19) Uani 1 1 d .
C7 C 0.2831(5) 0.3302(3) 0.4425(2) 0.0372(9) Uani 1 1 d .
C12 C 0.3233(6) 0.2357(3) 0.4332(2) 0.0371(9) Uani 1 1 d .
C13 C 0.2547(5) 0.1713(3) 0.4713(2) 0.0363(9) Uani 1 1 d .
C1 C 0.2262(7) 0.4904(4) 0.5868(3) 0.0556(13) Uani 1 1 d .
H1 H 0.219(7) 0.452(3) 0.620(3) 0.067 Uiso 1 1 d R
N1 N 0.2687(5) 0.3627(2) 0.5107(2) 0.0419(8) Uani 1 1 d .
N2 N 0.2635(5) 0.4719(2) 0.3796(2) 0.0462(9) Uani 1 1 d .
C9 C 0.2964(6) 0.3450(3) 0.3005(2) 0.0411(10) Uani 1 1 d .
C3 C 0.2220(7) 0.6330(3) 0.5286(4) 0.0619(14) Uani 1 1 d .
H3 H 0.210(7) 0.701(4) 0.535(3) 0.074 Uiso 1 1 d R
C5 C 0.2499(6) 0.5060(3) 0.4507(3) 0.0455(11) Uani 1 1 d .
C8 C 0.2755(6) 0.3860(3) 0.3754(2) 0.0403(10) Uani 1 1 d .
C2 C 0.2151(7) 0.5793(3) 0.5924(3) 0.0599(14) Uani 1 1 d .
H2 H 0.207(7) 0.602(3) 0.645(3) 0.072 Uiso 1 1 d R
N3 N 0.5803(5) 0.1610(2) 0.3914(2) 0.0403(8) Uani 1 1 d .
N4 N 0.5567(5) 0.2713(2) 0.2604(2) 0.0455(9) Uani 1 1 d .
C16 C 0.6893(6) 0.2089(3) 0.2749(2) 0.0433(10) Uani 1 1 d .
C11 C 0.4524(6) 0.2202(3) 0.3767(2) 0.0382(9) Uani 1 1 d .
C10 C 0.4391(6) 0.2760(3) 0.3099(2) 0.0390(10) Uani 1 1 d .
C15 C 0.7000(5) 0.1522(3) 0.3396(2) 0.0394(10) Uani 1 1 d .
C17 C 0.8228(7) 0.2005(4) 0.2248(3) 0.0566(13) Uani 1 1 d .
H17 H 0.819(6) 0.246(3) 0.184(3) 0.068 Uiso 1 1 d R
C19 C 0.9574(6) 0.0798(4) 0.3004(3) 0.0579(13) Uani 1 1 d .
H19 H 1.046605 0.036286 0.307674 0.069 Uiso 1 1 calc R
C20 C 0.8372(6) 0.0870(3) 0.3510(3) 0.0485(11) Uani 1 1 d .
H20 H 0.845(6) 0.047(3) 0.394(3) 0.058 Uiso 1 1 d R
C18 C 0.9504(7) 0.1363(4) 0.2376(3) 0.0627(14) Uani 1 1 d .
H18 H 1.035004 0.129832 0.203794 0.075 Uiso 1 1 calc R
C6 C 0.2482(6) 0.4516(3) 0.5151(3) 0.0428(10) Uani 1 1 d .
C14 C 0.1924(6) 0.3679(3) 0.2337(3) 0.0439(10) Uani 1 1 d .
C4 C 0.2387(7) 0.5981(3) 0.4585(3) 0.0562(13) Uani 1 1 d .
H4 H 0.235(7) 0.632(3) 0.414(3) 0.067 Uiso 1 1 d R
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 0.0000 0.0000 '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
N1 C7 C12 120.7(4)
N1 C7 C8 121.4(4)
C8 C7 C12 117.7(4)
C7 C12 C11 112.6(3)
C13 C12 C7 124.3(4)
C13 C12 C11 123.1(4)
Br2 C13 Br1 109.6(2)
C12 C13 Br1 125.4(3)
C12 C13 Br2 125.0(3)
C2 C1 C6 119.6(5)
C7 N1 C6 116.7(4)
C8 N2 C5 116.3(4)
C10 C9 C8 111.6(4)
C14 C9 C8 122.7(4)
C14 C9 C10 125.7(4)
C4 C3 C2 121.0(5)
N2 C5 C6 121.4(4)
N2 C5 C4 118.6(4)
C6 C5 C4 120.0(4)
C7 C8 C9 118.5(4)
N2 C8 C7 122.3(4)
N2 C8 C9 119.1(4)
C1 C2 C3 121.0(5)
C11 N3 C15 117.3(4)
C10 N4 C16 116.2(4)
N4 C16 C15 121.7(4)
N4 C16 C17 119.6(4)
C15 C16 C17 118.7(4)
N3 C11 C12 119.6(4)
N3 C11 C10 121.8(4)
C10 C11 C12 118.4(4)
N4 C10 C9 119.6(4)
N4 C10 C11 122.3(4)
C11 C10 C9 118.0(4)
N3 C15 C16 120.6(4)
N3 C15 C20 119.8(4)
C20 C15 C16 119.5(4)
C18 C17 C16 119.6(5)
C20 C19 C18 121.4(5)
C19 C20 C15 119.5(5)
C17 C18 C19 121.2(5)
N1 C6 C1 119.3(4)
N1 C6 C5 121.7(4)
C5 C6 C1 119.0(4)
Br3 C14 Br4 110.9(2)
C9 C14 Br4 124.1(3)
C9 C14 Br3 125.0(3)
C3 C4 C5 119.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br4 C14 1.878(4)
Br1 C13 1.885(4)
Br2 C13 1.875(4)
Br3 C14 1.868(4)
C7 C12 1.484(5)
C7 N1 1.316(5)
C7 C8 1.447(6)
C12 C13 1.330(5)
C12 C11 1.496(5)
C1 C2 1.363(7)
C1 C6 1.423(6)
N1 C6 1.367(5)
N2 C5 1.369(5)
N2 C8 1.315(5)
C9 C8 1.485(6)
C9 C10 1.480(6)
C9 C14 1.348(6)
C3 C2 1.394(7)
C3 C4 1.364(7)
C5 C6 1.404(6)
C5 C4 1.414(6)
N3 C11 1.304(5)
N3 C15 1.368(5)
N4 C16 1.361(5)
N4 C10 1.321(5)
C16 C15 1.420(6)
C16 C17 1.423(6)
C11 C10 1.440(6)
C15 C20 1.413(6)
C17 C18 1.353(7)
C19 C20 1.352(6)
C19 C18 1.395(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189566
