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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/38/7233836.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_7233836
loop_
_publ_author_name
'I. V. Klimovich'
'L. I. Leshanskaya'
'S. I. Troyanov'
'D. V. Anokhin'
'D. V. Novikov'
'A. A. Piryazev'
'D. A. Ivanov'
'N. N. Dremova'
'P. A. Troshin'
_publ_section_title
;
 Design of indigo derivatives as environment-friendly organic
 semiconductors for sustainable organic electronics
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              7621
_journal_page_last               7631
_journal_paper_doi               10.1039/C4TC00550C
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C16 H8 Cl2 N2 O2'
_chemical_formula_weight         331.14
_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_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.090(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.1129(8)
_cell_length_b                   4.5375(2)
_cell_length_c                   11.7091(7)
_cell_measurement_reflns_used    5514
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      4
_cell_volume                     654.30(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  IPDS(Stoe)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1114
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9060
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0300P)²+1.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                1352
_reflns_number_total             1748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000004.cif
_cod_data_source_block           PCOD1000004
_cod_original_cell_volume        654.30(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7233836
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.94730(6) 0.21264(16) 0.86998(6) 0.02176(19) Uani 1 1 d . . .
O1 O 0.58334(16) 1.0297(4) 0.73829(16) 0.0169(4) Uani 1 1 d . . .
N1 N 0.59110(18) 0.7235(5) 0.46722(19) 0.0151(4) Uani 1 1 d . . .
C1 C 0.5435(2) 0.9120(6) 0.5264(2) 0.0150(5) Uani 1 1 d . . .
C2 C 0.6045(2) 0.8912(6) 0.6593(2) 0.0154(5) Uani 1 1 d . . .
C3 C 0.6902(2) 0.6753(6) 0.6694(2) 0.0150(5) Uani 1 1 d . . .
C4 C 0.7738(2) 0.5668(6) 0.7698(2) 0.0159(5) Uani 1 1 d . . .
C5 C 0.8425(2) 0.3616(6) 0.7484(2) 0.0179(6) Uani 1 1 d . . .
C6 C 0.8303(2) 0.2651(7) 0.6304(2) 0.0187(5) Uani 1 1 d . . .
C7 C 0.7482(2) 0.3757(6) 0.5303(2) 0.0169(5) Uani 1 1 d . . .
C8 C 0.6780(2) 0.5817(6) 0.5512(2) 0.0153(5) Uani 1 1 d . . .
H1 H 0.566(3) 0.689(9) 0.385(4) 0.037(11) Uiso 1 1 d . . .
H4 H 0.780(3) 0.640(8) 0.850(3) 0.027(9) Uiso 1 1 d . . .
H6 H 0.884(3) 0.140(8) 0.621(3) 0.022(9) Uiso 1 1 d . . .
H7 H 0.739(2) 0.307(7) 0.446(3) 0.012(7) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0184(3) 0.0236(4) 0.0204(3) 0.0048(3) 0.0029(2) 0.0030(3)
O1 0.0242(10) 0.0162(10) 0.0122(8) -0.0003(7) 0.0088(7) 0.0008(8)
N1 0.0195(11) 0.0148(11) 0.0110(9) 0.0002(8) 0.0052(8) 0.0015(9)
C1 0.0216(14) 0.0129(12) 0.0118(11) 0.0000(10) 0.0072(10) -0.0024(10)
C2 0.0197(13) 0.0136(12) 0.0125(11) 0.0017(10) 0.0048(10) -0.0014(10)
C3 0.0200(12) 0.0135(12) 0.0127(11) 0.0008(9) 0.0072(9) -0.0026(10)
C4 0.0186(13) 0.0153(13) 0.0140(11) 0.0014(10) 0.0057(10) -0.0021(10)
C5 0.0177(12) 0.0170(14) 0.0160(12) 0.0038(10) 0.0019(10) -0.0012(10)
C6 0.0189(12) 0.0177(14) 0.0200(12) 0.0016(11) 0.0072(10) 0.0024(11)
C7 0.0205(13) 0.0166(13) 0.0142(11) -0.0003(10) 0.0068(10) -0.0002(10)
C8 0.0181(12) 0.0152(12) 0.0135(11) 0.0014(10) 0.0064(10) -0.0024(10)
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 C8 109.7(2) . .
C1 C1 N1 126.3(3) 3_676 .
C1 C1 C2 125.5(3) 3_676 .
N1 C1 C2 108.3(2) . .
O1 C2 C3 130.4(2) . .
O1 C2 C1 125.2(3) . .
C3 C2 C1 104.4(2) . .
C4 C3 C8 121.0(3) . .
C4 C3 C2 131.6(2) . .
C8 C3 C2 107.3(2) . .
C5 C4 C3 117.4(2) . .
C4 C5 C6 122.0(3) . .
C4 C5 Cl1 119.7(2) . .
C6 C5 Cl1 118.3(2) . .
C7 C6 C5 120.7(3) . .
C6 C7 C8 117.7(3) . .
N1 C8 C7 128.5(2) . .
N1 C8 C3 110.3(2) . .
C7 C8 C3 121.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.740(3) .
O1 C2 1.226(3) .
N1 C1 1.378(3) .
N1 C8 1.382(3) .
C1 C1 1.356(5) 3_676
C1 C2 1.488(4) .
C2 C3 1.465(4) .
C3 C4 1.393(4) .
C3 C8 1.404(3) .
C4 C5 1.377(4) .
C5 C6 1.406(4) .
C6 C7 1.385(4) .
C7 C8 1.390(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 136653217
