#------------------------------------------------------------------------------ #$Date: 2019-10-07 10:29:59 +0300 (Mon, 07 Oct 2019) $ #$Revision: 219121 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234407.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_7234407 loop_ _publ_author_name 'Oratai Pitayatanakul' 'Kodai Iijima' 'Minoru Ashizawa' 'Tadashi Kawamoto' 'Hidetoshi Matsumoto' 'Takehiko Mori' _publ_section_title ; An iodine effect in ambipolar organic field-effect transistors based on indigo derivatives ; _journal_name_full 'Journal of Materials Chemistry C' _journal_page_first 8612 _journal_page_last 8617 _journal_paper_doi 10.1039/C5TC01023C _journal_volume 3 _journal_year 2015 _chemical_formula_moiety 'C16 H8 I2 N2 O2' _chemical_formula_sum 'C16 H8 I2 N2 O2' _chemical_formula_weight 514.06 _chemical_melting_point_gt 573.15 _chemical_name_systematic 5,5'-diiodoindigo _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 95.3328(7) _cell_angle_gamma 90.0000 _cell_formula_units_Z 2 _cell_length_a 14.0666(3) _cell_length_b 4.38905(8) _cell_length_c 11.9563(3) _cell_measurement_reflns_used 7327 _cell_measurement_temperature 273 _cell_measurement_theta_max 68.23 _cell_measurement_theta_min 3.15 _cell_volume 734.98(3) _computing_cell_refinement 'RAPID AUTO' _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_data_reduction 'RAPID AUTO' _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 273 _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_reflns_av_R_equivalents 0.1359 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7874 _diffrn_reflns_theta_full 68.23 _diffrn_reflns_theta_max 68.23 _diffrn_standards_interval_count . _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 33.681 _exptl_absorpt_correction_T_max 0.668 _exptl_absorpt_correction_T_min 0.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_crystal_colour 'dark blue' _exptl_crystal_density_diffrn 2.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 480.00 _exptl_crystal_recrystallization_method Sublimation _exptl_crystal_size_max 0.097 _exptl_crystal_size_mid 0.078 _exptl_crystal_size_min 0.012 _refine_diff_density_max 1.910 _refine_diff_density_min -0.830 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 100 _refine_ls_number_reflns 1349 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0449 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0762P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1338 _reflns_number_gt 1185 _reflns_number_total 1349 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file J-Mater-Chem-C-2015-3-8612.cif _cod_data_source_block 20140331 _cod_depositor_comments ; The following automatic conversions were performed: data name '_chemical_melting_point' was changed to '_chemical_melting_point_gt' since the value was specified as 'more than' ('>') a certain temperature. The value '> 300C' was changed to '573.15' -- it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_original_cell_volume 734.97(3) _cod_database_code 7234407 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 I1 I 0.43365(2) 0.75743(5) -0.14867(3) 0.0384(3) Uani 1.0 4 d . . . O1 O 0.07442(16) -0.0254(6) -0.19384(18) 0.0367(7) Uani 1.0 4 d . . . N1 N 0.0836(4) 0.2685(6) 0.0800(4) 0.0292(10) Uani 1.0 4 d . . . C1 C 0.0396(3) 0.0847(9) -0.0042(3) 0.0295(8) Uani 1.0 4 d . . . C2 C 0.0944(3) 0.1082(9) -0.1042(3) 0.0271(8) Uani 1.0 4 d . . . C3 C 0.1636(3) 0.4047(9) 0.0409(3) 0.0273(8) Uani 1.0 4 d . . . C4 C 0.1740(4) 0.3123(10) -0.0692(4) 0.0286(9) Uani 1.0 4 d . . . C5 C 0.2290(3) 0.6022(9) 0.0974(3) 0.0343(9) Uani 1.0 4 d . . . C6 C 0.2512(3) 0.4114(9) -0.1253(3) 0.0307(8) Uani 1.0 4 d . . . C7 C 0.3058(4) 0.6984(10) 0.0413(5) 0.0363(11) Uani 1.0 4 d . . . C8 C 0.3160(3) 0.6018(9) -0.0686(3) 0.0312(8) Uani 1.0 4 d . . . H1 H 0.0645 0.2939 0.1457 0.0351 Uiso 1.0 4 calc R . . H5 H 0.2216 0.6675 0.1701 0.0411 Uiso 1.0 4 calc R . . H6 H 0.2582 0.3503 -0.1986 0.0368 Uiso 1.0 4 calc R . . H7 H 0.3511 0.8285 0.0772 0.0436 Uiso 1.0 4 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I1 0.0257(4) 0.0507(4) 0.0398(4) -0.00840(8) 0.0080(3) -0.00110(9) O1 0.0377(14) 0.0475(17) 0.0250(13) -0.0080(12) 0.0023(11) -0.0033(11) N1 0.026(3) 0.041(3) 0.021(3) -0.0059(11) 0.0032(17) -0.0045(10) C1 0.0226(16) 0.040(2) 0.0257(18) 0.0001(16) 0.0019(14) -0.0002(15) C2 0.0277(18) 0.032(2) 0.0208(17) 0.0011(16) 0.0000(14) 0.0032(16) C3 0.0244(16) 0.036(2) 0.0212(17) 0.0022(15) 0.0013(13) 0.0011(15) C4 0.024(2) 0.0361(19) 0.025(3) 0.0023(18) -0.0004(16) 0.0003(18) C5 0.035(2) 0.043(3) 0.0255(18) -0.0025(17) 0.0063(15) -0.0001(17) C6 0.0233(17) 0.042(3) 0.0273(18) 0.0007(15) 0.0054(14) 0.0019(16) C7 0.025(3) 0.051(3) 0.033(3) -0.0022(17) -0.000(2) -0.0007(18) C8 0.0242(16) 0.036(2) 0.0338(19) 0.0008(16) 0.0054(14) 0.0041(17) 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 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) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; I I -0.3257 6.8362 ; 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 C1 N1 C3 108.9(4) yes . . . N1 C1 C1 125.5(4) yes . . 3_555 N1 C1 C2 108.3(4) yes . . . C1 C1 C2 126.2(3) yes 3_555 . . O1 C2 C1 125.1(3) yes . . . O1 C2 C4 130.3(4) yes . . . C1 C2 C4 104.6(3) yes . . . N1 C3 C4 110.5(4) yes . . . N1 C3 C5 128.5(4) yes . . . C4 C3 C5 121.0(4) yes . . . C2 C4 C3 107.6(4) yes . . . C2 C4 C6 131.4(4) yes . . . C3 C4 C6 121.1(4) yes . . . C3 C5 C7 117.6(4) yes . . . C4 C6 C8 117.6(4) yes . . . C5 C7 C8 120.9(4) yes . . . I1 C8 C6 119.3(3) yes . . . I1 C8 C7 118.9(3) yes . . . C6 C8 C7 121.8(4) yes . . . C1 N1 H1 125.533 no . . . C3 N1 H1 125.522 no . . . C3 C5 H5 121.183 no . . . C7 C5 H5 121.194 no . . . C4 C6 H6 121.188 no . . . C8 C6 H6 121.185 no . . . C5 C7 H7 119.564 no . . . C8 C7 H7 119.558 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 I1 C8 2.101(4) yes . . O1 C2 1.231(4) yes . . N1 C1 1.390(6) yes . . N1 C3 1.393(6) yes . . C1 C1 1.351(5) yes . 3_555 C1 C2 1.485(5) yes . . C2 C4 1.465(6) yes . . C3 C4 1.399(6) yes . . C3 C5 1.393(5) yes . . C4 C6 1.397(6) yes . . C5 C7 1.389(7) yes . . C6 C8 1.370(5) yes . . C7 C8 1.401(7) yes . . N1 H1 0.860 no . . C5 H5 0.930 no . . C6 H6 0.930 no . . C7 H7 0.930 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 3.511(6) no . . O1 N1 2.914(6) no . 3_555 O1 C1 2.992(4) no . 3_555 O1 C3 3.516(4) no . . O1 C6 3.186(4) no . . N1 C2 3.036(6) no . 3_555 C1 C3 3.570(5) no . 3_555 C3 C8 2.754(5) no . . C4 C7 2.757(7) no . . C5 C6 2.836(5) no . . O1 O1 3.237(4) no . 2_544 O1 O1 3.237(4) no . 2_554 O1 N1 2.943(6) no . 4_554 O1 C3 3.557(4) no . 4_554 O1 C4 3.500(5) no . 1_545 O1 C5 3.476(5) no . 4_554 O1 C6 3.547(5) no . 1_545 N1 O1 2.943(6) no . 4_555 N1 N1 3.534(6) no . 3_565 N1 C1 3.405(5) no . 3_565 N1 C5 3.564(5) no . 1_545 C1 N1 3.405(5) no . 3_565 C1 C3 3.473(5) no . 1_545 C1 C5 3.529(5) no . 1_545 C3 O1 3.557(4) no . 4_555 C3 C1 3.473(5) no . 1_565 C4 O1 3.500(5) no . 1_565 C4 C7 3.462(7) no . 1_545 C5 O1 3.476(5) no . 4_555 C5 N1 3.564(5) no . 1_565 C5 C1 3.529(5) no . 1_565 C6 O1 3.547(5) no . 1_565 C7 C4 3.462(7) no . 1_565 I1 H6 3.0604 no . . I1 H7 3.0539 no . . O1 H1 2.3976 no . 3_555 O1 H6 3.0713 no . . N1 H5 2.7575 no . . C1 H1 2.7034 no . 3_555 C2 H1 3.1628 no . . C2 H1 2.8550 no . 3_555 C2 H6 2.8627 no . . C3 H6 3.2766 no . . C3 H7 3.2233 no . . C4 H1 3.1176 no . . C4 H5 3.2722 no . . C5 H1 2.7873 no . . C6 H7 3.2496 no . . C7 H6 3.2640 no . . C8 H5 3.2708 no . . H1 H5 2.7448 no . . H5 H7 2.3293 no . . I1 H5 3.5361 no . 4_564 I1 H6 3.5980 no . 1_565 I1 H7 3.5668 no . 3_675 I1 H7 3.3945 no . 4_564 O1 H1 2.1639 no . 4_554 O1 H5 2.8189 no . 4_554 N1 H5 3.3905 no . 1_545 N1 H6 3.4787 no . 4_555 C1 H1 3.4617 no . 3_565 C2 H1 3.4527 no . 3_565 C2 H1 3.0114 no . 4_554 C2 H5 3.5838 no . 4_554 C3 H6 3.4575 no . 4_555 C5 H6 3.1429 no . 4_555 C5 H6 3.4212 no . 4_565 C6 H5 3.5248 no . 4_554 C6 H5 3.0634 no . 4_564 C8 H5 3.4324 no . 4_564 H1 O1 2.1639 no . 4_555 H1 C1 3.4617 no . 3_565 H1 C2 3.4527 no . 3_565 H1 C2 3.0114 no . 4_555 H1 H5 3.5223 no . 1_545 H1 H6 3.2169 no . 4_555 H5 I1 3.5361 no . 4_565 H5 O1 2.8189 no . 4_555 H5 N1 3.3905 no . 1_565 H5 C2 3.5838 no . 4_555 H5 C6 3.5248 no . 4_555 H5 C6 3.0634 no . 4_565 H5 C8 3.4324 no . 4_565 H5 H1 3.5223 no . 1_565 H5 H6 2.7832 no . 4_555 H5 H6 2.6571 no . 4_565 H6 I1 3.5980 no . 1_545 H6 N1 3.4787 no . 4_554 H6 C3 3.4575 no . 4_554 H6 C5 3.1429 no . 4_554 H6 C5 3.4212 no . 4_564 H6 H1 3.2169 no . 4_554 H6 H5 2.7832 no . 4_554 H6 H5 2.6571 no . 4_564 H6 H7 3.3952 no . 4_564 H7 I1 3.5668 no . 3_675 H7 I1 3.3945 no . 4_565 H7 H6 3.3952 no . 4_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 H1 O1 . . 3_555 2.914(6) 0.860 2.398 119.1 no N1 H1 O1 . . 4_555 2.943(6) 0.860 2.164 150.5 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 C1 N1 C3 C4 -0.3(4) no . . . . C1 N1 C3 C5 -179.1(3) no . . . . C3 N1 C1 C1 179.4(3) no . . . 3_555 C3 N1 C1 C2 -0.8(4) no . . . . N1 C1 C1 N1 180.0(4) no . . 3_555 3_555 N1 C1 C1 C2 -0.2(6) no . . 3_555 3_555 N1 C1 C2 O1 -179.7(3) no . . . . N1 C1 C2 C4 1.5(4) no . . . . C1 C1 C2 O1 0.1(6) no 3_555 . . . C1 C1 C2 C4 -178.7(4) no 3_555 . . . C2 C1 C1 N1 0.2(6) no . . 3_555 3_555 C2 C1 C1 C2 180.0(4) no . . 3_555 3_555 O1 C2 C4 C3 179.7(4) no . . . . O1 C2 C4 C6 -1.3(7) no . . . . C1 C2 C4 C3 -1.7(4) no . . . . C1 C2 C4 C6 177.4(4) no . . . . N1 C3 C4 C2 1.3(4) no . . . . N1 C3 C4 C6 -177.9(3) no . . . . N1 C3 C5 C7 177.3(3) no . . . . C4 C3 C5 C7 -1.3(5) no . . . . C5 C3 C4 C2 -179.8(3) no . . . . C5 C3 C4 C6 1.0(6) no . . . . C2 C4 C6 C8 -178.9(4) no . . . . C3 C4 C6 C8 0.1(6) no . . . . C3 C5 C7 C8 0.7(6) no . . . . C4 C6 C8 I1 179.9(3) no . . . . C4 C6 C8 C7 -0.7(5) no . . . . C5 C7 C8 I1 179.8(3) no . . . . C5 C7 C8 C6 0.3(6) no . . . .