#------------------------------------------------------------------------------
#$Date: 2019-09-17 11:39:08 +0300 (Tue, 17 Sep 2019) $
#$Revision: 218360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/39/7233902.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_7233902
loop_
_publ_author_name
'Oratai Pitayatanakul'
'Toshiki Higashino'
'Tomofumi Kadoya'
'Masaki Tanaka'
'Hirotaka Kojima'
'Minoru Ashizawa'
'Tadashi Kawamoto'
'Hidetoshi Matsumoto'
'Ken Ishikawa'
'Takehiko Mori'
_publ_section_title
;
 High performance ambipolar organic field-effect transistors based on
 indigo derivatives
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9311
_journal_page_last               9317
_journal_paper_doi               10.1039/C4TC01563K
_journal_volume                  2
_journal_year                    2014
_chemical_formula_moiety         'C16 H8 Br2 N2 O2'
_chemical_formula_sum            'C16 H8 Br2 N2 O2'
_chemical_formula_weight         420.06
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.23(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   13.794(7)
_cell_length_b                   4.462(4)
_cell_length_c                   11.963(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      17.23
_cell_measurement_theta_min      14.96
_cell_volume                     690.9(8)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        WinAFC
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2356
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_standards_decay_%        -0.665
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.892
_exptl_absorpt_correction_T_max  0.308
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             408.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.740
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     116
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0562P)²+0.9432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                1201
_reflns_number_total             2015
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            1000001.cif
_cod_data_source_block           PCOD1000001
_cod_original_cell_volume        690.8(8)
_cod_database_code               7233902
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.44404(4) 0.20426(13) 0.36230(4) 0.0493(2) Uani 1.0 4 d . . .
O1 O 0.0793(3) 1.0089(8) 0.2338(3) 0.0385(7) Uani 1.0 4 d . . .
N1 N 0.0870(3) 0.7284(9) -0.0363(3) 0.0342(8) Uani 1.0 4 d . . .
C1 C 0.3317(4) 0.3641(11) 0.2342(4) 0.0364(10) Uani 1.0 4 d . . .
C2 C 0.2635(4) 0.5601(11) 0.2575(4) 0.0342(9) Uani 1.0 4 d . . .
C3 C 0.3215(4) 0.2761(11) 0.1183(5) 0.0398(10) Uani 1.0 4 d . . .
C4 C 0.1837(3) 0.6697(10) 0.1617(4) 0.0289(8) Uani 1.0 4 d . . .
C5 C 0.2396(4) 0.3870(12) 0.0209(5) 0.0378(10) Uani 1.0 4 d . . .
C6 C 0.1724(3) 0.5851(10) 0.0444(4) 0.0312(9) Uani 1.0 4 d . . .
C7 C 0.0999(4) 0.8783(10) 0.1544(4) 0.0301(9) Uani 1.0 4 d . . .
C8 C 0.0424(3) 0.9115(10) 0.0246(4) 0.0302(9) Uani 1.0 4 d . . .
H1 H 0.257(4) 0.612(11) 0.335(4) 0.031(12) Uiso 1.0 4 d . . .
H2 H 0.372(4) 0.146(10) 0.104(4) 0.023(11) Uiso 1.0 4 d . . .
H3 H 0.219(4) 0.317(11) -0.056(5) 0.033(12) Uiso 1.0 4 d . . .
H4 H 0.069(4) 0.700(11) -0.112(5) 0.039(14) Uiso 1.0 4 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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C6 N1 C8 109.4(4) yes . . .
Br1 C1 C2 119.8(4) yes . . .
Br1 C1 C3 117.9(4) yes . . .
C2 C1 C3 122.4(4) yes . . .
C1 C2 C4 117.4(4) yes . . .
C1 C3 C5 120.0(5) yes . . .
C2 C4 C6 121.1(5) yes . . .
C2 C4 C7 131.6(4) yes . . .
C6 C4 C7 107.3(3) yes . . .
C3 C5 C6 117.5(5) yes . . .
N1 C6 C4 110.1(4) yes . . .
N1 C6 C5 128.3(4) yes . . .
C4 C6 C5 121.6(4) yes . . .
O1 C7 C4 130.1(4) yes . . .
O1 C7 C8 125.3(4) yes . . .
C4 C7 C8 104.6(4) yes . . .
N1 C8 C7 108.6(4) yes . . .
N1 C8 C8 126.2(4) yes . . 3_575
C7 C8 C8 125.2(5) yes . . 3_575
C6 N1 H4 122(4) no . . .
C8 N1 H4 129(4) no . . .
C1 C2 H1 129(3) no . . .
C4 C2 H1 113(3) no . . .
C1 C3 H2 121(3) no . . .
C5 C3 H2 119(3) no . . .
C3 C5 H3 126(3) no . . .
C6 C5 H3 115(4) no . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C1 1.902(4) yes . .
O1 C7 1.229(6) yes . .
N1 C6 1.393(5) yes . .
N1 C8 1.373(7) yes . .
C1 C2 1.382(7) yes . .
C1 C3 1.400(7) yes . .
C2 C4 1.376(6) yes . .
C3 C5 1.403(6) yes . .
C4 C6 1.409(6) yes . .
C4 C7 1.463(7) yes . .
C5 C6 1.378(7) yes . .
C7 C8 1.487(5) yes . .
C8 C8 1.364(6) yes . 3_575
N1 H4 0.86(5) no . .
C2 H1 0.99(6) no . .
C3 H2 0.97(5) no . .
C5 H3 0.92(5) no . .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 3.501(6) no . .
O1 N1 2.911(5) no . 3_575
O1 C2 3.169(6) no . .
O1 C6 3.517(6) no . .
O1 C8 2.985(5) no . 3_575
N1 C2 3.596(6) no . .
N1 C7 3.034(6) no . 3_575
C1 C6 2.740(6) no . .
C2 C5 2.842(7) no . .
C3 C4 2.765(7) no . .
C6 C8 3.579(7) no . 3_575
O1 O1 3.241(5) no . 2_545
O1 O1 3.241(5) no . 2_555
O1 N1 2.915(6) no . 4_565
O1 C2 3.476(6) no . 1_565
O1 C4 3.517(6) no . 1_565
O1 C5 3.413(6) no . 4_565
O1 C6 3.511(5) no . 4_565
O1 C7 3.593(7) no . 2_555
N1 O1 2.915(6) no . 4_564
N1 N1 3.480(7) no . 3_565
N1 C5 3.541(7) no . 1_565
N1 C8 3.395(7) no . 3_565
C2 O1 3.476(6) no . 1_545
C3 C4 3.447(7) no . 1_545
C4 O1 3.517(6) no . 1_545
C4 C3 3.447(7) no . 1_565
C5 O1 3.413(6) no . 4_564
C5 N1 3.541(7) no . 1_545
C5 C8 3.462(7) no . 1_545
C6 O1 3.511(5) no . 4_564
C6 C8 3.465(7) no . 1_545
C6 C8 3.560(7) no . 3_565
C7 O1 3.593(7) no . 2_545
C8 N1 3.395(7) no . 3_565
C8 C5 3.462(7) no . 1_565
C8 C6 3.465(7) no . 1_565
C8 C6 3.560(7) no . 3_565
Br1 H1 3.08(5) no . .
Br1 H2 2.91(4) no . .
O1 H1 2.93(5) no . .
O1 H4 2.44(5) no . 3_575
N1 H3 2.66(6) no . .
C1 H3 3.29(5) no . .
C2 H2 3.31(5) no . .
C3 H1 3.37(6) no . .
C4 H3 3.22(6) no . .
C4 H4 3.11(5) no . .
C5 H4 2.72(5) no . .
C6 H1 3.27(5) no . .
C6 H2 3.26(5) no . .
C7 H1 2.75(4) no . .
C7 H4 3.17(6) no . .
C7 H4 2.90(6) no . 3_575
C8 H4 2.75(6) no . 3_575
H2 H3 2.44(6) no . .
H3 H4 2.58(7) no . .
Br1 H2 3.48(5) no . 2_645
Br1 H2 3.12(5) no . 2_655
Br1 H2 3.43(5) no . 4_555
Br1 H3 3.56(7) no . 4_555
O1 H1 3.56(5) no . 1_565
O1 H3 2.70(5) no . 4_565
O1 H4 2.11(6) no . 4_565
N1 H1 3.30(6) no . 4_564
N1 H3 3.25(6) no . 1_565
C1 H3 3.47(6) no . 4_555
C2 H3 3.02(6) no . 4_555
C5 H1 3.21(5) no . 4_554
C5 H1 3.22(5) no . 4_564
C6 H1 3.39(6) no . 4_564
C7 H3 3.55(5) no . 4_565
C7 H4 3.40(5) no . 3_565
C7 H4 2.99(6) no . 4_565
C8 H3 3.43(6) no . 1_565
C8 H4 3.47(6) no . 3_565
H1 O1 3.56(5) no . 1_545
H1 N1 3.30(6) no . 4_565
H1 C5 3.21(5) no . 4_555
H1 C5 3.22(5) no . 4_565
H1 C6 3.39(6) no . 4_565
H1 H2 3.27(6) no . 4_555
H1 H3 2.47(8) no . 4_555
H1 H3 2.99(7) no . 4_565
H1 H4 3.00(8) no . 4_565
H2 Br1 3.12(5) no . 2_645
H2 Br1 3.48(5) no . 2_655
H2 Br1 3.43(5) no . 4_554
H2 H1 3.27(6) no . 4_554
H3 Br1 3.56(7) no . 4_554
H3 O1 2.70(5) no . 4_564
H3 N1 3.25(6) no . 1_545
H3 C1 3.47(6) no . 4_554
H3 C2 3.02(6) no . 4_554
H3 C7 3.55(5) no . 4_564
H3 C8 3.43(6) no . 1_545
H3 H1 2.47(8) no . 4_554
H3 H1 2.99(7) no . 4_564
H3 H4 3.37(7) no . 1_545
H4 O1 2.11(6) no . 4_564
H4 C7 3.40(5) no . 3_565
H4 C7 2.99(6) no . 4_564
H4 C8 3.47(6) no . 3_565
H4 H1 3.00(8) no . 4_564
H4 H3 3.37(7) no . 1_565
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H4 O1 . . 3_575 2.911(5) 0.86(6) 2.44(5) 115(5) no
N1 H4 O1 . . 4_564 2.915(6) 0.86(6) 2.11(5) 154(5) no
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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 N1 C8 C7 -2.1(5) no . . . .
C6 N1 C8 C8 179.6(4) no . . . 3_575
C8 N1 C6 C4 1.2(5) no . . . .
C8 N1 C6 C5 -178.9(4) no . . . .
Br1 C1 C2 C4 179.9(3) no . . . .
Br1 C1 C3 C5 179.7(3) no . . . .
C2 C1 C3 C5 -0.2(8) no . . . .
C3 C1 C2 C4 -0.2(7) no . . . .
C1 C2 C4 C6 -0.0(7) no . . . .
C1 C2 C4 C7 -179.5(4) no . . . .
C1 C3 C5 C6 0.9(7) no . . . .
C2 C4 C6 N1 -179.3(4) no . . . .
C2 C4 C6 C5 0.8(7) no . . . .
C2 C4 C7 O1 -0.4(9) no . . . .
C2 C4 C7 C8 178.0(5) no . . . .
C6 C4 C7 O1 -179.9(5) no . . . .
C6 C4 C7 C8 -1.5(5) no . . . .
C7 C4 C6 N1 0.3(5) no . . . .
C7 C4 C6 C5 -179.6(4) no . . . .
C3 C5 C6 N1 178.9(5) no . . . .
C3 C5 C6 C4 -1.2(7) no . . . .
O1 C7 C8 N1 -179.2(4) no . . . .
O1 C7 C8 C8 -1.0(8) no . . . 3_575
C4 C7 C8 N1 2.2(5) no . . . .
C4 C7 C8 C8 -179.5(4) no . . . 3_575
N1 C8 C8 N1 -180.0(4) no . . 3_575 3_575
N1 C8 C8 C7 -2.0(8) no . . 3_575 3_575
C7 C8 C8 N1 2.0(8) no . . 3_575 3_575
C7 C8 C8 C7 -180.0(5) no . . 3_575 3_575
