#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/20/1552051.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_1552051
loop_
_publ_author_name
'Wei Liu'
'Xin Luo'
'Yang Bao'
'Yan Peng Liu'
'Guo-Hong Ning'
'Ibrahim Abdelwahab'
'Linjun Li'
'Chang Tai Nai'
'Zhi Gang Hu'
'Dan Zhao'
'Bin Liu'
'Su Ying Quek'
'Kian Ping Loh'
_publ_section_title
;
 A two-dimensional conjugated aromatic polymer via C-C coupling reaction
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              563
_journal_page_last               570
_journal_paper_doi               10.1038/nchem.2696
_journal_volume                  9
_journal_year                    2017
_chemical_formula_sum            'C34 H14 Br4 N4'
_chemical_formula_weight         798.13
_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'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 99.857(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2408(10)
_cell_length_b                   4.6467(4)
_cell_length_c                   25.9293(19)
_cell_measurement_reflns_used    6517
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      3.46
_cell_volume                     1334.36(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8157
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.580
_diffrn_reflns_theta_min         3.460
_diffrn_source                   'Sealed Microfocusing Source'
_exptl_absorpt_coefficient_mu    7.638
_exptl_absorpt_correction_T_max  0.9694
_exptl_absorpt_correction_T_min  0.3137
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.179
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+18.9752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2231
_reflns_number_total             2373
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nchem.2696-s2.cif
_cod_data_source_block           f218
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Integration' was
changed to 'integration' in accordance with the built-in table
derived from the CIF Core dictionary named 'cif_core.dic' version
2.4.5 last updated on 2014-11-21.

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1552051
_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_min   0.150
_shelx_estimated_absorpt_t_max   0.844
_shelxl_version_number           2014/6
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.32163(6) 0.59290(18) 0.42270(3) 0.0240(2) Uani 1 1 d . . . . .
Br2 Br 1.14503(6) 1.08897(19) 0.27562(3) 0.0257(2) Uani 1 1 d . . . . .
N1 N 0.7866(5) 0.2772(11) 0.45976(19) 0.0112(10) Uani 1 1 d . . . . .
N2 N 1.0038(4) 0.4144(11) 0.42315(18) 0.0094(10) Uani 1 1 d . . . . .
C1 C 0.6801(5) 0.6264(13) 0.4020(2) 0.0095(12) Uani 1 1 d . . . . .
C2 C 0.5711(6) 0.5588(14) 0.4205(2) 0.0133(13) Uani 1 1 d . . . . .
H2B H 0.5710 0.4180 0.4470 0.016 Uiso 1 1 calc R U . . .
C3 C 0.4679(6) 0.6958(15) 0.4000(2) 0.0167(14) Uani 1 1 d . . . . .
C4 C 0.4650(6) 0.9098(15) 0.3621(2) 0.0150(13) Uani 1 1 d . . . . .
H4A H 0.3918 1.0077 0.3490 0.018 Uiso 1 1 calc R U . . .
C5 C 0.5692(6) 0.9765(14) 0.3440(2) 0.0138(13) Uani 1 1 d . . . . .
H5A H 0.5672 1.1206 0.3179 0.017 Uiso 1 1 calc R U . . .
C6 C 0.6792(5) 0.8379(14) 0.3630(2) 0.0108(12) Uani 1 1 d . . . . .
C7 C 0.7917(6) 0.9033(13) 0.3433(2) 0.0107(12) Uani 1 1 d . . . . .
C8 C 0.7951(5) 1.1115(14) 0.3040(2) 0.0117(12) Uani 1 1 d . . . . .
H8A H 0.7240 1.2169 0.2908 0.014 Uiso 1 1 calc R U . . .
C9 C 0.8998(6) 1.1660(14) 0.2841(2) 0.0130(13) Uani 1 1 d . . . . .
H9A H 0.9004 1.3054 0.2574 0.016 Uiso 1 1 calc R U . . .
C10 C 1.0033(6) 1.0141(15) 0.3039(2) 0.0153(13) Uani 1 1 d . . . . .
C11 C 1.0045(5) 0.8138(14) 0.3428(2) 0.0120(12) Uani 1 1 d . . . . .
H11A H 1.0769 0.7130 0.3560 0.014 Uiso 1 1 calc R U . . .
C12 C 0.8991(5) 0.7576(13) 0.3630(2) 0.0092(12) Uani 1 1 d . . . . .
C13 C 0.9018(5) 0.5419(13) 0.4044(2) 0.0101(12) Uani 1 1 d . . . . .
C14 C 0.7906(5) 0.4739(13) 0.4235(2) 0.0089(12) Uani 1 1 d . . . . .
C15 C 0.8918(5) 0.1406(13) 0.4793(2) 0.0106(12) Uani 1 1 d . . . . .
C16 C 1.0019(6) 0.2114(13) 0.4611(2) 0.0098(12) Uani 1 1 d . . . . .
C17 C 0.8914(6) -0.0713(14) 0.5179(2) 0.0113(12) Uani 1 1 d . . . . .
H17 H 0.8184 -0.1188 0.5298 0.014 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C14 N1 C15 117.2(5) . .
C13 N2 C16 117.3(5) . .
C6 C1 C2 119.6(5) . .
C6 C1 C14 121.0(5) . .
C2 C1 C14 119.4(5) . .
C3 C2 C1 119.7(6) . .
C3 C2 H2B 120.2 . .
C1 C2 H2B 120.2 . .
C2 C3 C4 121.9(6) . .
C2 C3 Br1 119.4(5) . .
C4 C3 Br1 118.7(5) . .
C5 C4 C3 118.9(6) . .
C5 C4 H4A 120.5 . .
C3 C4 H4A 120.5 . .
C4 C5 C6 122.0(6) . .
C4 C5 H5A 119.0 . .
C6 C5 H5A 119.0 . .
C5 C6 C1 118.0(5) . .
C5 C6 C7 122.6(6) . .
C1 C6 C7 119.5(5) . .
C12 C7 C8 117.8(5) . .
C12 C7 C6 120.6(5) . .
C8 C7 C6 121.6(6) . .
C9 C8 C7 121.6(6) . .
C9 C8 H8A 119.2 . .
C7 C8 H8A 119.2 . .
C10 C9 C8 118.9(6) . .
C10 C9 H9A 120.5 . .
C8 C9 H9A 120.5 . .
C11 C10 C9 121.4(6) . .
C11 C10 Br2 120.4(5) . .
C9 C10 Br2 118.2(5) . .
C10 C11 C12 120.0(6) . .
C10 C11 H11A 120.0 . .
C12 C11 H11A 120.0 . .
C11 C12 C7 120.3(6) . .
C11 C12 C13 119.3(5) . .
C7 C12 C13 120.4(5) . .
N2 C13 C14 121.6(5) . .
N2 C13 C12 119.2(5) . .
C14 C13 C12 119.2(5) . .
N1 C14 C1 118.7(5) . .
N1 C14 C13 121.9(5) . .
C1 C14 C13 119.3(5) . .
N1 C15 C17 119.0(5) . .
N1 C15 C16 120.9(6) . .
C17 C15 C16 120.1(6) . .
N2 C16 C17 119.1(5) . 3_756
N2 C16 C15 121.0(5) . .
C17 C16 C15 119.9(6) 3_756 .
C16 C17 C15 119.9(6) 3_756 .
C16 C17 H17 120.0 3_756 .
C15 C17 H17 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.899(6) .
Br2 C10 1.897(6) .
N1 C14 1.317(8) .
N1 C15 1.361(8) .
N2 C13 1.309(8) .
N2 C16 1.367(8) .
C1 C6 1.409(9) .
C1 C2 1.425(8) .
C1 C14 1.455(8) .
C2 C3 1.349(10) .
C2 H2B 0.9500 .
C3 C4 1.395(9) .
C4 C5 1.370(9) .
C4 H4A 0.9500 .
C5 C6 1.406(9) .
C5 H5A 0.9500 .
C6 C7 1.475(8) .
C7 C12 1.403(9) .
C7 C8 1.410(9) .
C8 C9 1.386(9) .
C8 H8A 0.9500 .
C9 C10 1.382(9) .
C9 H9A 0.9500 .
C10 C11 1.370(9) .
C11 C12 1.400(8) .
C11 H11A 0.9500 .
C12 C13 1.465(8) .
C13 C14 1.456(8) .
C15 C17 1.405(9) .
C15 C16 1.436(8) .
C16 C17 1.390(9) 3_756
C17 C16 1.390(9) 3_756
C17 H17 0.9500 .
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
C6 C1 C2 C3 0.7(9) . . . .
C14 C1 C2 C3 -178.8(6) . . . .
C1 C2 C3 C4 -1.9(10) . . . .
C1 C2 C3 Br1 177.3(5) . . . .
C2 C3 C4 C5 1.9(10) . . . .
Br1 C3 C4 C5 -177.3(5) . . . .
C3 C4 C5 C6 -0.7(10) . . . .
C4 C5 C6 C1 -0.4(9) . . . .
C4 C5 C6 C7 178.8(6) . . . .
C2 C1 C6 C5 0.4(9) . . . .
C14 C1 C6 C5 180.0(6) . . . .
C2 C1 C6 C7 -178.8(5) . . . .
C14 C1 C6 C7 0.7(9) . . . .
C5 C6 C7 C12 -179.4(6) . . . .
C1 C6 C7 C12 -0.2(9) . . . .
C5 C6 C7 C8 0.3(9) . . . .
C1 C6 C7 C8 179.5(6) . . . .
C12 C7 C8 C9 1.9(9) . . . .
C6 C7 C8 C9 -177.8(6) . . . .
C7 C8 C9 C10 -0.7(9) . . . .
C8 C9 C10 C11 -0.5(10) . . . .
C8 C9 C10 Br2 179.3(5) . . . .
C9 C10 C11 C12 0.5(10) . . . .
Br2 C10 C11 C12 -179.3(5) . . . .
C10 C11 C12 C7 0.7(9) . . . .
C10 C11 C12 C13 179.7(6) . . . .
C8 C7 C12 C11 -1.9(9) . . . .
C6 C7 C12 C11 177.8(6) . . . .
C8 C7 C12 C13 179.1(5) . . . .
C6 C7 C12 C13 -1.2(9) . . . .
C16 N2 C13 C14 0.8(8) . . . .
C16 N2 C13 C12 -179.0(5) . . . .
C11 C12 C13 N2 2.8(9) . . . .
C7 C12 C13 N2 -178.2(5) . . . .
C11 C12 C13 C14 -177.0(5) . . . .
C7 C12 C13 C14 2.0(8) . . . .
C15 N1 C14 C1 -179.5(5) . . . .
C15 N1 C14 C13 0.7(8) . . . .
C6 C1 C14 N1 -179.7(6) . . . .
C2 C1 C14 N1 -0.2(8) . . . .
C6 C1 C14 C13 0.1(9) . . . .
C2 C1 C14 C13 179.6(5) . . . .
N2 C13 C14 N1 -1.4(9) . . . .
C12 C13 C14 N1 178.4(5) . . . .
N2 C13 C14 C1 178.8(5) . . . .
C12 C13 C14 C1 -1.5(8) . . . .
C14 N1 C15 C17 -179.8(5) . . . .
C14 N1 C15 C16 0.5(8) . . . .
C13 N2 C16 C17 -180.0(5) . . . 3_756
C13 N2 C16 C15 0.4(8) . . . .
N1 C15 C16 N2 -1.1(9) . . . .
C17 C15 C16 N2 179.2(5) . . . .
N1 C15 C16 C17 179.3(5) . . . 3_756
C17 C15 C16 C17 -0.4(10) . . . 3_756
N1 C15 C17 C16 -179.3(5) . . . 3_756
C16 C15 C17 C16 0.4(10) . . . 3_756
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168303106
