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#$Date: 2018-02-04 00:30:57 +0200 (Sun, 04 Feb 2018) $
#$Revision: 206135 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/43/4514333.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_4514333
loop_
_publ_author_name
'Liu, Wei'
'Ulaganathan, Mani'
'Abdelwahab, Ibrahim'
'Luo, Xin'
'Chen, Zhongxin'
'Rong Tan, Sherman Jun'
'Wang, Xiaowei'
'Liu, Yanpeng'
'Geng, Dechao'
'Bao, Yang'
'Chen, Jianyi'
'Loh, Kian Ping'
_publ_section_title
;
 Two-Dimensional Polymer Synthesized via Solid-State Polymerization for
 High-Performance Supercapacitors.
;
_journal_issue                   1
_journal_name_full               'ACS nano'
_journal_page_first              852
_journal_page_last               860
_journal_paper_doi               10.1021/acsnano.7b08354
_journal_volume                  12
_journal_year                    2018
_chemical_formula_moiety         'C17 H7 Br2 N2'
_chemical_formula_sum            'C17 H7 Br2 N2'
_chemical_formula_weight         399.07
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                96.687(3)
_cell_angle_beta                 96.766(2)
_cell_angle_gamma                95.701(2)
_cell_formula_units_Z            2
_cell_length_a                   3.8581(2)
_cell_length_b                   10.5438(6)
_cell_length_c                   16.1258(9)
_cell_measurement_reflns_used    2686
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.439
_cell_measurement_theta_min      2.476
_cell_volume                     642.72(6)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX v2014.11.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX v2014.11.0.'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution
'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13295
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.439
_diffrn_reflns_theta_min         2.476
_exptl_absorpt_coefficient_mu    6.298
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_correction_T_min  0.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.062
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             386
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0352
_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)+(0.0279P)²+0.3997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2420
_reflns_number_total             3210
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nn7b08354_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4514332--4514333.cif.'
_cod_database_code               4514333
_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   0.304
_shelx_estimated_absorpt_t_max   0.858
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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
Br1 Br 0.96765(8) 0.24264(3) 0.74926(2) 0.01444(9) Uani 1 1 d . .
Br2 Br 0.26156(9) 0.74932(3) 1.04409(2) 0.01701(10) Uani 1 1 d . .
N1 N 0.5910(7) 1.0426(2) 0.33726(15) 0.0103(5) Uani 1 1 d . .
N2 N 0.6466(7) 0.7664(2) 0.55087(15) 0.0104(5) Uani 1 1 d . .
C1 C 0.5168(8) 1.1538(3) 0.31446(19) 0.0106(6) Uani 1 1 d . .
C2 C 0.5455(8) 1.0221(3) 0.41756(19) 0.0105(6) Uani 1 1 d . .
C3 C 0.6166(8) 0.9049(3) 0.44402(19) 0.0119(7) Uani 1 1 d . .
H3 H 0.6941 0.8408 0.4063 0.014 Uiso 1 1 calc R U
C4 C 0.5738(8) 0.8819(3) 0.52560(19) 0.0101(6) Uani 1 1 d . .
C5 C 0.6025(8) 0.7490(3) 0.62903(18) 0.0102(6) Uani 1 1 d . .
C6 C 0.6785(8) 0.6271(3) 0.65842(19) 0.0095(6) Uani 1 1 d . .
C7 C 0.7915(8) 0.5318(3) 0.60312(19) 0.0119(7) Uani 1 1 d . .
H7 H 0.8131 0.5469 0.5469 0.014 Uiso 1 1 calc R U
C8 C 0.8719(8) 0.4164(3) 0.62848(19) 0.0126(7) Uani 1 1 d . .
H8 H 0.9464 0.3520 0.5905 0.015 Uiso 1 1 calc R U
C9 C 0.8407(8) 0.3973(3) 0.7113(2) 0.0120(6) Uani 1 1 d . .
C10 C 0.7264(8) 0.4885(3) 0.76703(19) 0.0110(6) Uani 1 1 d . .
H10 H 0.7060 0.4722 0.8231 0.013 Uiso 1 1 calc R U
C11 C 0.6402(8) 0.6053(3) 0.74128(19) 0.0109(6) Uani 1 1 d . .
C12 C 0.5135(8) 0.7040(3) 0.79904(19) 0.0104(6) Uani 1 1 d . .
C13 C 0.4402(8) 0.8223(3) 0.77170(19) 0.0100(6) Uani 1 1 d . .
C14 C 0.3268(8) 0.9171(3) 0.82690(19) 0.0119(6) Uani 1 1 d . .
H14 H 0.2825 0.9969 0.8083 0.014 Uiso 1 1 calc R U
C15 C 0.2784(8) 0.8967(3) 0.9077(2) 0.0138(7) Uani 1 1 d . .
H15 H 0.2013 0.9615 0.9450 0.017 Uiso 1 1 calc R U
C16 C 0.3448(8) 0.7791(3) 0.93367(19) 0.0138(7) Uani 1 1 d . .
C17 C 0.4612(8) 0.6848(3) 0.88157(19) 0.0120(7) Uani 1 1 d . .
H17 H 0.5067 0.6059 0.9014 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 0.0033 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'
N N 0.0061 0.0033 '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'
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
C1 N1 C2 116.9(3) . .
C5 N2 C4 117.1(3) . .
N1 C1 C5 122.3(3) . 2_676
N1 C1 C13 118.0(3) . 2_676
C5 C1 C13 119.7(3) 2_676 2_676
N1 C2 C3 118.8(3) . .
N1 C2 C4 121.3(3) . 2_676
C3 C2 C4 119.8(3) . 2_676
C4 C3 C2 120.0(3) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
N2 C4 C3 119.3(3) . .
N2 C4 C2 120.5(3) . 2_676
C3 C4 C2 120.2(3) . 2_676
N2 C5 C1 121.8(3) . 2_676
N2 C5 C6 118.7(3) . .
C1 C5 C6 119.4(3) 2_676 .
C7 C6 C11 119.9(3) . .
C7 C6 C5 119.5(3) . .
C11 C6 C5 120.6(3) . .
C8 C7 C6 121.5(3) . .
C8 C7 H7 119.3 . .
C6 C7 H7 119.3 . .
C7 C8 C9 118.0(3) . .
C7 C8 H8 121.0 . .
C9 C8 H8 121.0 . .
C10 C9 C8 122.0(3) . .
C10 C9 Br1 119.1(2) . .
C8 C9 Br1 118.9(2) . .
C9 C10 C11 120.3(3) . .
C9 C10 H10 119.9 . .
C11 C10 H10 119.9 . .
C10 C11 C6 118.4(3) . .
C10 C11 C12 121.5(3) . .
C6 C11 C12 120.1(3) . .
C17 C12 C13 118.0(3) . .
C17 C12 C11 122.0(3) . .
C13 C12 C11 119.9(3) . .
C14 C13 C12 120.0(3) . .
C14 C13 C1 119.7(3) . 2_676
C12 C13 C1 120.2(3) . 2_676
C15 C14 C13 121.1(3) . .
C15 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
C14 C15 C16 118.5(3) . .
C14 C15 H15 120.7 . .
C16 C15 H15 120.7 . .
C17 C16 C15 121.9(3) . .
C17 C16 Br2 119.8(2) . .
C15 C16 Br2 118.3(2) . .
C16 C17 C12 120.4(3) . .
C16 C17 H17 119.8 . .
C12 C17 H17 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C9 1.896(3) .
Br2 C16 1.902(3) .
N1 C1 1.317(4) .
N1 C2 1.366(4) .
N2 C5 1.323(4) .
N2 C4 1.373(4) .
C1 C5 1.438(4) 2_676
C1 C13 1.466(4) 2_676
C2 C3 1.395(4) .
C2 C4 1.433(4) 2_676
C3 C4 1.391(4) .
C3 H3 0.9500 .
C4 C2 1.433(4) 2_676
C5 C1 1.438(4) 2_676
C5 C6 1.465(4) .
C6 C7 1.402(4) .
C6 C11 1.404(4) .
C7 C8 1.380(4) .
C7 H7 0.9500 .
C8 C9 1.391(4) .
C8 H8 0.9500 .
C9 C10 1.379(4) .
C10 C11 1.402(4) .
C10 H10 0.9500 .
C11 C12 1.474(4) .
C12 C17 1.404(4) .
C12 C13 1.414(4) .
C13 C14 1.398(4) .
C13 C1 1.466(4) 2_676
C14 C15 1.377(4) .
C14 H14 0.9500 .
C15 C16 1.391(4) .
C15 H15 0.9500 .
C16 C17 1.371(4) .
C17 H17 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 Br1 0.95 3.04 3.905(3) 151.7 2_766
C3 H3 Br1 0.95 3.04 3.905(3) 151.7 2_766
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_4
C2 N1 C1 C5 0.8(4) . 2_676
C2 N1 C1 C13 -179.4(3) . 2_676
C1 N1 C2 C3 179.2(3) . .
C1 N1 C2 C4 -0.7(4) . 2_676
N1 C2 C3 C4 179.7(3) . .
C4 C2 C3 C4 -0.5(5) 2_676 .
C5 N2 C4 C3 179.9(3) . .
C5 N2 C4 C2 -0.2(4) . 2_676
C2 C3 C4 N2 -179.6(3) . .
C2 C3 C4 C2 0.5(5) . 2_676
C4 N2 C5 C1 0.1(4) . 2_676
C4 N2 C5 C6 -179.8(3) . .
N2 C5 C6 C7 -0.7(4) . .
C1 C5 C6 C7 179.4(3) 2_676 .
N2 C5 C6 C11 179.1(3) . .
C1 C5 C6 C11 -0.8(4) 2_676 .
C11 C6 C7 C8 -1.0(5) . .
C5 C6 C7 C8 178.9(3) . .
C6 C7 C8 C9 -0.5(5) . .
C7 C8 C9 C10 1.3(5) . .
C7 C8 C9 Br1 -177.5(2) . .
C8 C9 C10 C11 -0.6(5) . .
Br1 C9 C10 C11 178.2(2) . .
C9 C10 C11 C6 -1.0(5) . .
C9 C10 C11 C12 179.3(3) . .
C7 C6 C11 C10 1.7(4) . .
C5 C6 C11 C10 -178.1(3) . .
C7 C6 C11 C12 -178.5(3) . .
C5 C6 C11 C12 1.6(4) . .
C10 C11 C12 C17 -2.2(5) . .
C6 C11 C12 C17 178.1(3) . .
C10 C11 C12 C13 177.9(3) . .
C6 C11 C12 C13 -1.8(4) . .
C17 C12 C13 C14 1.4(4) . .
C11 C12 C13 C14 -178.7(3) . .
C17 C12 C13 C1 -178.7(3) . 2_676
C11 C12 C13 C1 1.2(4) . 2_676
C12 C13 C14 C15 -1.2(5) . .
C1 C13 C14 C15 178.9(3) 2_676 .
C13 C14 C15 C16 0.0(5) . .
C14 C15 C16 C17 1.0(5) . .
C14 C15 C16 Br2 -177.8(2) . .
C15 C16 C17 C12 -0.7(5) . .
Br2 C16 C17 C12 178.1(2) . .
C13 C12 C17 C16 -0.5(5) . .
C11 C12 C17 C16 179.6(3) . .
