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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/7/23/38/7233834.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_7233834
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            'C18 H8 F6 N2 O2'
_chemical_formula_weight         398.26
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'I b a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.2110(10)
_cell_length_b                   8.6741(7)
_cell_length_c                   12.6299(6)
_cell_measurement_reflns_used    10000
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      5
_cell_volume                     3090.6(3)
_computing_cell_refinement       XDS
_computing_data_collection       XDS
_computing_data_reduction        XDS
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  MAR225
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  Si(111)
_diffrn_radiation_source         'BL 14.2, PSF, BESSY, Berlin, Germany'
_diffrn_radiation_wavelength     0.84344
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24964
_diffrn_reflns_theta_full        30.10
_diffrn_reflns_theta_max         34.71
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       0.035(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    restrain
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                3703
_reflns_number_total             3750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000002.cif
_cod_data_source_block           PCOD1000002
_cod_original_sg_symbol_H-M      Iba2
_cod_database_code               7233834
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, 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
F1 F 0.68660(3) 0.46573(12) 0.60568(9) 0.0291(2) Uani 1 1 d . . .
F2 F 0.63353(4) 0.33067(11) 0.68578(10) 0.0324(3) Uani 1 1 d . . .
F3 F 0.65380(3) 0.55213(11) 0.74723(9) 0.0256(2) Uani 1 1 d . . .
F4 F 0.25869(4) 1.20485(12) 0.27801(9) 0.0310(2) Uani 1 1 d . . .
F5 F 0.21513(3) 1.24602(12) 0.41511(9) 0.0282(2) Uani 1 1 d . . .
F6 F 0.26867(4) 1.41023(10) 0.37084(11) 0.0329(3) Uani 1 1 d . . .
O1 O 0.48400(3) 0.79319(13) 0.33883(9) 0.0193(2) Uani 1 1 d . . .
O2 O 0.41785(4) 0.95730(11) 0.71163(8) 0.0181(2) Uani 1 1 d . . .
N1 N 0.49707(4) 0.78166(13) 0.61511(10) 0.0148(2) Uani 1 1 d . . .
H1 H 0.4896 0.8027 0.6812 0.018 Uiso 1 1 calc R . .
N2 N 0.40826(4) 0.96205(12) 0.43506(10) 0.0149(2) Uani 1 1 d . . .
H2 H 0.4176 0.9442 0.3697 0.018 Uiso 1 1 calc R . .
C1 C 0.47218(4) 0.82997(13) 0.52690(11) 0.0133(2) Uani 1 1 d . . .
C2 C 0.49667(4) 0.76996(14) 0.43050(12) 0.0139(2) Uani 1 1 d . . .
C3 C 0.53712(4) 0.68286(14) 0.47259(12) 0.0150(3) Uani 1 1 d . . .
C4 C 0.57319(5) 0.60259(15) 0.42050(11) 0.0180(3) Uani 1 1 d . . .
H4 H 0.5736 0.5943 0.3455 0.022 Uiso 1 1 calc R . .
C5 C 0.60868(5) 0.53487(15) 0.48194(13) 0.0192(3) Uani 1 1 d . . .
H5 H 0.6338 0.4796 0.4492 0.023 Uiso 1 1 calc R . .
C6 C 0.60683(4) 0.54926(14) 0.59201(12) 0.0152(3) Uani 1 1 d . . .
C7 C 0.57110(4) 0.62788(15) 0.64576(12) 0.0153(3) Uani 1 1 d . . .
H7 H 0.5707 0.6357 0.7208 0.018 Uiso 1 1 calc R . .
C8 C 0.53574(4) 0.69468(14) 0.58292(12) 0.0132(3) Uani 1 1 d . . .
C9 C 0.64558(5) 0.47552(16) 0.65715(13) 0.0191(3) Uani 1 1 d . . .
C10 C 0.43176(4) 0.91592(13) 0.52503(11) 0.0138(2) Uani 1 1 d . . .
C11 C 0.40517(4) 0.97259(14) 0.61937(12) 0.0140(2) Uani 1 1 d . . .
C12 C 0.36298(5) 1.04800(15) 0.57421(11) 0.0146(3) Uani 1 1 d . . .
C13 C 0.32390(5) 1.11924(15) 0.62163(12) 0.0171(3) Uani 1 1 d . . .
H13 H 0.3208 1.1235 0.6965 0.021 Uiso 1 1 calc R . .
C14 C 0.28972(5) 1.18356(15) 0.55590(12) 0.0175(3) Uani 1 1 d . . .
H14 H 0.2625 1.2315 0.5856 0.021 Uiso 1 1 calc R . .
C15 C 0.29535(4) 1.17768(14) 0.44590(12) 0.0158(3) Uani 1 1 d . . .
C16 C 0.33394(4) 1.10878(14) 0.39698(12) 0.0158(3) Uani 1 1 d . . .
H16 H 0.3373 1.1076 0.3222 0.019 Uiso 1 1 calc R . .
C17 C 0.36757(4) 1.04117(14) 0.46369(12) 0.0144(3) Uani 1 1 d . . .
C18 C 0.25951(5) 1.25884(17) 0.37708(13) 0.0203(3) Uani 1 1 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 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'
F F 0.0171 0.0103 '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 109.16(12) . .
C10 N2 C17 109.15(12) . .
C10 C1 N1 127.23(12) . .
C10 C1 C2 124.31(12) . .
N1 C1 C2 108.45(10) . .
O1 C2 C3 130.68(13) . .
O1 C2 C1 125.21(12) . .
C3 C2 C1 104.10(12) . .
C4 C3 C8 121.74(13) . .
C4 C3 C2 130.68(14) . .
C8 C3 C2 107.56(12) . .
C5 C4 C3 118.04(13) . .
C4 C5 C6 119.25(12) . .
C7 C6 C5 123.75(13) . .
C7 C6 C9 117.75(13) . .
C5 C6 C9 118.50(12) . .
C6 C7 C8 116.21(13) . .
N1 C8 C3 110.72(12) . .
N1 C8 C7 128.25(13) . .
C3 C8 C7 121.00(12) . .
F1 C9 F3 107.26(12) . .
F1 C9 F2 106.89(12) . .
F3 C9 F2 106.14(13) . .
F1 C9 C6 112.99(13) . .
F3 C9 C6 112.23(11) . .
F2 C9 C6 110.95(12) . .
C1 C10 N2 125.24(12) . .
C1 C10 C11 125.98(12) . .
N2 C10 C11 108.77(11) . .
O2 C11 C12 130.67(12) . .
O2 C11 C10 125.23(12) . .
C12 C11 C10 104.10(12) . .
C13 C12 C17 121.16(13) . .
C13 C12 C11 131.87(14) . .
C17 C12 C11 106.97(12) . .
C14 C13 C12 117.95(13) . .
C13 C14 C15 119.99(12) . .
C16 C15 C14 123.15(13) . .
C16 C15 C18 118.08(14) . .
C14 C15 C18 118.64(13) . .
C15 C16 C17 116.43(13) . .
N2 C17 C16 127.80(14) . .
N2 C17 C12 110.91(12) . .
C16 C17 C12 121.28(12) . .
F4 C18 F6 106.95(13) . .
F4 C18 F5 106.81(12) . .
F6 C18 F5 106.33(12) . .
F4 C18 C15 112.82(12) . .
F6 C18 C15 111.22(12) . .
F5 C18 C15 112.31(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C9 1.3298(17) .
F2 C9 1.3510(16) .
F3 C9 1.3378(19) .
F4 C18 1.336(2) .
F5 C18 1.3457(15) .
F6 C18 1.3407(16) .
O1 C2 1.2284(19) .
O2 C11 1.226(2) .
N1 C1 1.3819(17) .
N1 C8 1.3874(15) .
N2 C10 1.3750(17) .
N2 C17 1.3855(15) .
C1 C10 1.3626(16) .
C1 C2 1.4935(18) .
C2 C3 1.4681(17) .
C3 C4 1.3976(17) .
C3 C8 1.398(2) .
C4 C5 1.3963(19) .
C5 C6 1.397(2) .
C6 C7 1.3936(18) .
C6 C9 1.5103(19) .
C7 C8 1.4001(17) .
C10 C11 1.4913(18) .
C11 C12 1.4729(18) .
C12 C13 1.3986(18) .
C12 C17 1.403(2) .
C13 C14 1.3893(19) .
C14 C15 1.399(2) .
C15 C16 1.3873(18) .
C15 C18 1.5077(18) .
C16 C17 1.3977(18) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 136862245
