#------------------------------------------------------------------------------
#$Date: 2016-11-09 08:03:36 +0100 (Wed 09 de Nov de 2016) $
#$Revision: 188353 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/70/7227039.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_7227039
loop_
_publ_author_name
'Ashizawa, Minoru'
'Hasegawa, Tsukasa'
'Kawauchi, Susumu'
'Masunaga, Hiroyasu'
'Hikima, Takaaki'
'Sato, Hiroyasu'
'Matsumoto, Hidetoshi'
_publ_section_title
;
 Structure-Property Relationship of Two Structural Isomers of
 Thiophene-Flanked Diazaisoindigo on Carrier-Transport Properties
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA17424H
_journal_year                    2016
_chemical_formula_moiety         'C34 H36 N4 O2 S2'
_chemical_formula_sum            'C34 H36 N4 O2 S2'
_chemical_formula_weight         596.80
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-10-29 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                99.8742(10)
_cell_angle_beta                 98.6417(11)
_cell_angle_gamma                101.4850(10)
_cell_formula_units_Z            1
_cell_length_a                   5.02134(9)
_cell_length_b                   9.79352(18)
_cell_length_c                   16.0988(3)
_cell_measurement_reflns_used    7738
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      4.71
_cell_volume                     750.27(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8771
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.204
_diffrn_reflns_theta_min         4.710
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.908
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             316.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     94
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0860P)²+0.0154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2294
_reflns_number_total             2692
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c6ra17424h2.cif
_cod_data_source_block           6_6_T_DAII
_cod_database_code               7227039
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.2588(6) 0.8695(3) 0.27340(15) 0.0465(4) Uani 0.558(2) 1 d D U P A 1
O1 O 0.9617(2) 0.32330(11) 0.11116(6) 0.0469(3) Uani 1 1 d . . . . .
N1 N 0.7273(2) 0.49245(12) 0.15162(7) 0.0369(3) Uani 1 1 d . . . . .
N2 N 0.5365(2) 0.69518(12) 0.16717(7) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.116(3) 1.0163(9) 0.2872(8) 0.0437(15) Uani 0.558(2) 1 d D U P A 1
H1 H 0.0225 1.0389 0.3315 0.052 Uiso 0.558(2) 1 calc R U P A 1
C2 C 0.155(4) 1.0952(17) 0.2267(9) 0.0489(19) Uani 0.558(2) 1 d D U P A 1
H2 H 0.0925 1.1781 0.2246 0.059 Uiso 0.558(2) 1 calc R U P A 1
C3 C 0.3654(3) 0.90698(15) 0.18408(9) 0.0390(4) Uani 1 1 d D U . . .
C4 C 0.5102(3) 0.81392(14) 0.13705(9) 0.0378(4) Uani 1 1 d . . . . .
C5 C 0.6196(3) 0.84573(16) 0.06639(10) 0.0461(4) Uani 1 1 d . . . . .
H5 H 0.5977 0.9281 0.0474 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7607(3) 0.75664(16) 0.02376(9) 0.0445(4) Uani 1 1 d . . . . .
H6 H 0.8319 0.7781 -0.0238 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7941(3) 0.63462(14) 0.05340(8) 0.0340(3) Uani 1 1 d . . . . .
C8 C 0.6746(3) 0.61415(14) 0.12594(8) 0.0344(3) Uani 1 1 d . . . . .
C9 C 0.9286(3) 0.51750(14) 0.03207(8) 0.0332(3) Uani 1 1 d . . . . .
C10 C 0.8820(3) 0.42948(14) 0.10024(9) 0.0360(3) Uani 1 1 d . . . . .
C11 C 0.6315(3) 0.43774(15) 0.22363(8) 0.0391(4) Uani 1 1 d . . . . .
H11A H 0.6488 0.3399 0.2187 0.047 Uiso 1 1 calc R U . . .
H11B H 0.4368 0.4376 0.2200 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7900(3) 0.52347(15) 0.31070(9) 0.0435(4) Uani 1 1 d . . . . .
H12A H 0.7690 0.6208 0.3167 0.052 Uiso 1 1 calc R U . . .
H12B H 0.9853 0.5253 0.3144 0.052 Uiso 1 1 calc R U . . .
C13 C 0.6876(3) 0.46068(17) 0.38393(10) 0.0445(4) Uani 1 1 d . . . . .
H13A H 0.7537 0.5318 0.4368 0.053 Uiso 1 1 calc R U . . .
H13B H 0.4869 0.4403 0.3728 0.053 Uiso 1 1 calc R U . . .
C14 C 0.7785(3) 0.32549(16) 0.39684(9) 0.0416(4) Uani 1 1 d . . . . .
H14A H 0.9790 0.3447 0.4065 0.050 Uiso 1 1 calc R U . . .
H14B H 0.7073 0.2529 0.3448 0.050 Uiso 1 1 calc R U . . .
C15 C 0.6799(3) 0.26832(18) 0.47207(10) 0.0478(4) Uani 1 1 d . . . . .
H15A H 0.7327 0.3445 0.5228 0.057 Uiso 1 1 calc R U . . .
H15B H 0.4794 0.2389 0.4593 0.057 Uiso 1 1 calc R U . . .
C16 C 0.7960(4) 0.1442(2) 0.49153(12) 0.0621(5) Uani 1 1 d . . . . .
H16A H 0.7396 0.0671 0.4423 0.093 Uiso 1 1 calc R U . . .
H16B H 0.7279 0.1138 0.5396 0.093 Uiso 1 1 calc R U . . .
H16C H 0.9944 0.1728 0.5051 0.093 Uiso 1 1 calc R U . . .
C17 C 0.3021(18) 1.0351(8) 0.1669(5) 0.100(4) Uani 0.558(2) 1 d D U P A 1
H17 H 0.3516 1.0753 0.1215 0.120 Uiso 0.558(2) 1 calc R U P A 1
S1A S 0.3040(3) 1.05366(15) 0.15657(11) 0.0426(4) Uani 0.442(2) 1 d D U P A 2
C17A C 0.242(3) 0.8774(15) 0.2535(6) 0.053(3) Uani 0.442(2) 1 d D U P A 2
H17A H 0.2440 0.7969 0.2767 0.064 Uiso 0.442(2) 1 calc R U P A 2
C1A C 0.134(5) 1.089(2) 0.2362(11) 0.047(2) Uani 0.442(2) 1 d D U P A 2
H1A H 0.0625 1.1697 0.2468 0.056 Uiso 0.442(2) 1 calc R U P A 2
C2A C 0.113(4) 0.9877(12) 0.2833(11) 0.050(2) Uani 0.442(2) 1 d D U P A 2
H2A H 0.0247 0.9898 0.3301 0.061 Uiso 0.442(2) 1 calc R U P A 2
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
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(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
C3 S1 C1 92.2(5) .
C10 N1 C8 110.80(11) .
C10 N1 C11 124.20(11) .
C8 N1 C11 125.00(11) .
C8 N2 C4 115.58(12) .
C2 C1 S1 112.8(10) .
C2 C1 H1 123.6 .
S1 C1 H1 123.6 .
C1 C2 C17 111.4(11) .
C1 C2 H2 124.3 .
C17 C2 H2 124.3 .
C17A C3 C4 124.6(5) .
C17 C3 C4 128.7(4) .
C17A C3 S1A 111.5(5) .
C4 C3 S1A 123.70(12) .
C17 C3 S1 111.2(4) .
C4 C3 S1 120.11(14) .
N2 C4 C5 121.76(13) .
N2 C4 C3 116.02(13) .
C5 C4 C3 122.21(14) .
C6 C5 C4 121.03(14) .
C6 C5 H5 119.5 .
C4 C5 H5 119.5 .
C5 C6 C7 118.79(14) .
C5 C6 H6 120.6 .
C7 C6 H6 120.6 .
C6 C7 C8 114.91(13) .
C6 C7 C9 137.69(13) .
C8 C7 C9 107.37(11) .
N2 C8 N1 121.96(12) .
N2 C8 C7 127.92(13) .
N1 C8 C7 110.11(12) .
C9 C9 C7 132.55(15) 2_765
C9 C9 C10 122.93(15) 2_765
C7 C9 C10 104.52(11) .
O1 C10 N1 123.39(13) .
O1 C10 C9 129.44(13) .
N1 C10 C9 107.17(11) .
N1 C11 C12 113.43(12) .
N1 C11 H11A 108.9 .
C12 C11 H11A 108.9 .
N1 C11 H11B 108.9 .
C12 C11 H11B 108.9 .
H11A C11 H11B 107.7 .
C11 C12 C13 111.66(12) .
C11 C12 H12A 109.3 .
C13 C12 H12A 109.3 .
C11 C12 H12B 109.3 .
C13 C12 H12B 109.3 .
H12A C12 H12B 107.9 .
C14 C13 C12 114.65(13) .
C14 C13 H13A 108.6 .
C12 C13 H13A 108.6 .
C14 C13 H13B 108.6 .
C12 C13 H13B 108.6 .
H13A C13 H13B 107.6 .
C13 C14 C15 113.23(13) .
C13 C14 H14A 108.9 .
C15 C14 H14A 108.9 .
C13 C14 H14B 108.9 .
C15 C14 H14B 108.9 .
H14A C14 H14B 107.7 .
C16 C15 C14 113.48(13) .
C16 C15 H15A 108.9 .
C14 C15 H15A 108.9 .
C16 C15 H15B 108.9 .
C14 C15 H15B 108.9 .
H15A C15 H15B 107.7 .
C15 C16 H16A 109.5 .
C15 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C15 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
C3 C17 C2 112.4(8) .
C3 C17 H17 123.8 .
C2 C17 H17 123.8 .
C3 S1A C1A 93.7(6) .
C3 C17A C2A 110.3(11) .
C3 C17A H17A 124.8 .
C2A C17A H17A 124.8 .
C2A C1A S1A 112.0(13) .
C2A C1A H1A 124.0 .
S1A C1A H1A 124.0 .
C1A C2A C17A 112.3(14) .
C1A C2A H2A 123.8 .
C17A C2A H2A 123.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C3 1.680(3) .
S1 C1 1.726(8) .
O1 C10 1.2162(16) .
N1 C10 1.3702(18) .
N1 C8 1.3867(16) .
N1 C11 1.4631(16) .
N2 C8 1.3148(18) .
N2 C4 1.3565(17) .
C1 C2 1.356(11) .
C1 H1 0.9300 .
C2 C17 1.420(12) .
C2 H2 0.9300 .
C3 C17A 1.403(10) .
C3 C17 1.415(7) .
C3 C4 1.458(2) .
C3 S1A 1.646(2) .
C4 C5 1.391(2) .
C5 C6 1.386(2) .
C5 H5 0.9300 .
C6 C7 1.3910(19) .
C6 H6 0.9300 .
C7 C8 1.4164(18) .
C7 C9 1.4606(18) .
C9 C9 1.377(3) 2_765
C9 C10 1.5243(19) .
C11 C12 1.5160(19) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.5289(19) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.520(2) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.5257(19) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.507(2) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17 0.9300 .
S1A C1A 1.668(13) .
C17A C2A 1.416(14) .
C17A H17A 0.9300 .
C1A C2A 1.349(14) .
C1A H1A 0.9300 .
C2A H2A 0.9300 .
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
C3 S1 C1 C2 -1.7(11) . .
S1 C1 C2 C17 0.4(17) . .
C1 S1 C3 C17 2.5(6) . .
C1 S1 C3 C4 -179.3(4) . .
C8 N2 C4 C5 0.9(2) . .
C8 N2 C4 C3 -178.02(12) . .
C17A C3 C4 N2 -3.7(7) . .
C17 C3 C4 N2 -178.5(4) . .
S1A C3 C4 N2 -178.23(12) . .
S1 C3 C4 N2 3.6(2) . .
C17A C3 C4 C5 177.4(7) . .
C17 C3 C4 C5 2.6(5) . .
S1A C3 C4 C5 2.8(2) . .
S1 C3 C4 C5 -175.36(17) . .
N2 C4 C5 C6 0.0(3) . .
C3 C4 C5 C6 178.83(14) . .
C4 C5 C6 C7 -0.6(3) . .
C5 C6 C7 C8 0.3(2) . .
C5 C6 C7 C9 -177.54(15) . .
C4 N2 C8 N1 177.39(11) . .
C4 N2 C8 C7 -1.3(2) . .
C10 N1 C8 N2 -177.96(12) . .
C11 N1 C8 N2 2.1(2) . .
C10 N1 C8 C7 0.90(16) . .
C11 N1 C8 C7 -179.08(12) . .
C6 C7 C8 N2 0.6(2) . .
C9 C7 C8 N2 179.15(13) . .
C6 C7 C8 N1 -178.14(11) . .
C9 C7 C8 N1 0.37(15) . .
C6 C7 C9 C9 -3.1(3) . 2_765
C8 C7 C9 C9 178.90(19) . 2_765
C6 C7 C9 C10 176.66(16) . .
C8 C7 C9 C10 -1.33(14) . .
C8 N1 C10 O1 177.92(13) . .
C11 N1 C10 O1 -2.1(2) . .
C8 N1 C10 C9 -1.72(15) . .
C11 N1 C10 C9 178.25(11) . .
C9 C9 C10 O1 2.0(3) 2_765 .
C7 C9 C10 O1 -177.75(14) . .
C9 C9 C10 N1 -178.34(16) 2_765 .
C7 C9 C10 N1 1.87(15) . .
C10 N1 C11 C12 105.59(16) . .
C8 N1 C11 C12 -74.44(17) . .
N1 C11 C12 C13 -178.72(12) . .
C11 C12 C13 C14 74.79(17) . .
C12 C13 C14 C15 178.27(13) . .
C13 C14 C15 C16 -173.44(13) . .
C4 C3 C17 C2 179.2(9) . .
S1 C3 C17 C2 -2.7(11) . .
C1 C2 C17 C3 1.4(17) . .
C17A C3 S1A C1A 3.2(11) . .
C4 C3 S1A C1A 178.4(9) . .
C4 C3 C17A C2A -178.6(9) . .
S1A C3 C17A C2A -3.5(13) . .
C3 S1A C1A C2A -2.1(17) . .
S1A C1A C2A C17A 0(2) . .
C3 C17A C2A C1A 2(2) . .
