#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:50:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180216 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/02/7110228.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_7110228
loop_
_publ_author_name
'Wan Yue'
'Tao He'
'Matthias Stolte'
'Marcel Gsanger'
'Frank Wurthner'
_publ_section_title
;
 Cyanated isoindigos for n-type and ambipolar organic thin film
 transistors
;
_journal_name_full               Chem.Commun.
_journal_page_first              545
_journal_paper_doi               10.1039/c3cc48037b
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C34 H40 N4 O2'
_chemical_formula_sum            'C34 H40 N4 O2'
_chemical_formula_weight         536.70
_chemical_name_common            dicyano-isoindigo
_chemical_name_systematic
;
6,6'-dicyano-N.N'-(1-octyl)isoindigo 
;
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                107.491(2)
_cell_angle_beta                 90.824(2)
_cell_angle_gamma                93.038(2)
_cell_formula_units_Z            1
_cell_length_a                   5.2943(4)
_cell_length_b                   9.7777(8)
_cell_length_c                   14.7860(12)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.41
_cell_measurement_theta_min      3.14
_cell_volume                     728.63(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multi_layered_optics
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.256
_diffrn_reflns_theta_min         3.135
_diffrn_source                   'Incoatec ImuS_microsource_with_mirror'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.749
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0677P)²+0.1776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2707
_reflns_number_total             2869
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c3cc48037b.txt
_cod_data_source_block           yw27b_c
_cod_database_code               7110228
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
C1 C 0.7606(2) 1.02482(11) 0.60577(7) 0.0192(2) Uani 1 1 d . .
C2 C 0.8969(2) 0.96525(11) 0.51293(7) 0.0182(2) Uani 1 1 d . .
C3 C 0.75566(19) 0.82741(11) 0.46533(8) 0.0187(2) Uani 1 1 d . .
C4 C 0.5514(2) 0.81400(11) 0.52393(7) 0.0187(2) Uani 1 1 d . .
C5 C 0.7813(2) 0.71562(12) 0.38177(8) 0.0215(2) Uani 1 1 d . .
H5 H 0.9173 0.7201 0.3414 0.026 Uiso 1 1 calc R U
C6 C 0.6078(2) 0.59784(12) 0.35768(8) 0.0224(2) Uani 1 1 d . .
H6 H 0.6266 0.5218 0.3009 0.027 Uiso 1 1 calc R U
C7 C 0.4060(2) 0.59014(11) 0.41608(8) 0.0208(2) Uani 1 1 d . .
C8 C 0.3756(2) 0.69883(12) 0.50127(8) 0.0208(2) Uani 1 1 d . .
H8 H 0.2399 0.6934 0.5416 0.025 Uiso 1 1 calc R U
C9 C 0.2252(2) 0.46817(12) 0.38786(8) 0.0227(3) Uani 1 1 d . .
C10 C 0.3885(2) 0.95230(12) 0.68496(8) 0.0212(2) Uani 1 1 d . .
H10A H 0.2176 0.9097 0.6609 0.025 Uiso 1 1 calc R U
H10B H 0.3744 1.0563 0.7161 0.025 Uiso 1 1 calc R U
C11 C 0.4823(2) 0.88333(13) 0.75768(8) 0.0250(3) Uani 1 1 d . .
H11A H 0.6479 0.9307 0.7850 0.030 Uiso 1 1 calc R U
H11B H 0.5083 0.7808 0.7255 0.030 Uiso 1 1 calc R U
C12 C 0.2984(2) 0.89416(12) 0.83789(8) 0.0232(3) Uani 1 1 d . .
H12A H 0.2851 0.9965 0.8742 0.028 Uiso 1 1 calc R U
H12B H 0.1285 0.8549 0.8105 0.028 Uiso 1 1 calc R U
C13 C 0.3837(2) 0.81227(13) 0.90494(8) 0.0255(3) Uani 1 1 d . .
H13A H 0.5445 0.8591 0.9374 0.031 Uiso 1 1 calc R U
H13B H 0.4180 0.7133 0.8669 0.031 Uiso 1 1 calc R U
C14 C 0.1927(2) 0.80417(12) 0.97991(8) 0.0249(3) Uani 1 1 d . .
H14A H 0.1728 0.9021 1.0230 0.030 Uiso 1 1 calc R U
H14B H 0.0264 0.7668 0.9482 0.030 Uiso 1 1 calc R U
C15 C 0.2727(2) 0.70803(13) 1.03827(8) 0.0267(3) Uani 1 1 d . .
H15A H 0.3231 0.6160 0.9945 0.032 Uiso 1 1 calc R U
H15B H 0.4233 0.7548 1.0783 0.032 Uiso 1 1 calc R U
C16 C 0.0685(2) 0.67599(13) 1.10190(8) 0.0280(3) Uani 1 1 d . .
H16A H -0.0859 0.6340 1.0628 0.034 Uiso 1 1 calc R U
H16B H 0.0256 0.7670 1.1489 0.034 Uiso 1 1 calc R U
C17 C 0.1525(3) 0.57246(14) 1.15403(9) 0.0356(3) Uani 1 1 d . .
H17A H 0.2064 0.4848 1.1080 0.053 Uiso 1 1 calc R U
H17B H 0.0110 0.5481 1.1895 0.053 Uiso 1 1 calc R U
H17C H 0.2940 0.6179 1.1981 0.053 Uiso 1 1 calc R U
N1 N 0.55737(17) 0.93258(10) 0.60493(6) 0.0199(2) Uani 1 1 d . .
N2 N 0.08344(19) 0.37065(11) 0.36399(7) 0.0280(2) Uani 1 1 d . .
O1 O 0.81290(15) 1.13267(8) 0.67172(6) 0.0263(2) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 C1 N1 122.99(10) .
O1 C1 C2 129.48(10) .
N1 C1 C2 107.53(9) .
C2 C2 C3 132.19(13) 2_776
C2 C2 C1 123.62(13) 2_776
C3 C2 C1 104.19(8) .
C5 C3 C4 117.66(10) .
C5 C3 C2 135.29(10) .
C4 C3 C2 107.05(9) .
C8 C4 N1 126.39(10) .
C8 C4 C3 123.46(10) .
N1 C4 C3 110.16(9) .
C6 C5 C3 120.00(10) .
C5 C6 C7 120.64(10) .
C6 C7 C8 121.21(10) .
C6 C7 C9 119.32(10) .
C8 C7 C9 119.47(10) .
C4 C8 C7 117.01(10) .
N2 C9 C7 178.85(12) .
N1 C10 C11 112.25(9) .
C10 C11 C12 112.66(9) .
C13 C12 C11 111.82(9) .
C12 C13 C14 114.36(9) .
C15 C14 C13 112.56(10) .
C16 C15 C14 114.30(10) .
C15 C16 C17 112.16(11) .
C1 N1 C4 110.95(9) .
C1 N1 C10 122.73(9) .
C4 N1 C10 126.01(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2177(13) .
C1 N1 1.3641(14) .
C1 C2 1.5288(14) .
C2 C2 1.375(2) 2_776
C2 C3 1.4760(15) .
C3 C5 1.3958(15) .
C3 C4 1.4204(14) .
C4 C8 1.3784(15) .
C4 N1 1.3929(14) .
C5 C6 1.3887(15) .
C6 C7 1.3963(15) .
C7 C8 1.4004(16) .
C7 C9 1.4426(15) .
C9 N2 1.1450(15) .
C10 N1 1.4657(13) .
C10 C11 1.5210(14) .
C11 C12 1.5281(14) .
C12 C13 1.5266(14) .
C13 C14 1.5277(15) .
C14 C15 1.5254(15) .
C15 C16 1.5238(16) .
C16 C17 1.5242(16) .
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
O1 C1 C2 C2 -4.3(2) . 2_776
N1 C1 C2 C2 176.31(12) . 2_776
O1 C1 C2 C3 175.91(11) . .
N1 C1 C2 C3 -3.51(11) . .
C2 C2 C3 C5 3.6(2) 2_776 .
C1 C2 C3 C5 -176.64(11) . .
C2 C2 C3 C4 -177.29(14) 2_776 .
C1 C2 C3 C4 2.50(10) . .
C5 C3 C4 C8 -1.68(15) . .
C2 C3 C4 C8 179.01(9) . .
C5 C3 C4 N1 178.60(9) . .
C2 C3 C4 N1 -0.71(11) . .
C4 C3 C5 C6 1.10(15) . .
C2 C3 C5 C6 -179.84(11) . .
C3 C5 C6 C7 0.37(16) . .
C5 C6 C7 C8 -1.39(16) . .
C5 C6 C7 C9 178.37(10) . .
N1 C4 C8 C7 -179.62(9) . .
C3 C4 C8 C7 0.70(16) . .
C6 C7 C8 C4 0.84(16) . .
C9 C7 C8 C4 -178.92(9) . .
N1 C10 C11 C12 -175.99(9) . .
C10 C11 C12 C13 174.64(10) . .
C11 C12 C13 C14 -173.22(10) . .
C12 C13 C14 C15 173.78(10) . .
C13 C14 C15 C16 -169.96(10) . .
C14 C15 C16 C17 176.55(10) . .
O1 C1 N1 C4 -176.22(10) . .
C2 C1 N1 C4 3.24(11) . .
O1 C1 N1 C10 -2.24(16) . .
C2 C1 N1 C10 177.22(9) . .
C8 C4 N1 C1 178.61(10) . .
C3 C4 N1 C1 -1.67(12) . .
C8 C4 N1 C10 4.88(17) . .
C3 C4 N1 C10 -175.41(9) . .
C11 C10 N1 C1 -87.40(12) . .
C11 C10 N1 C4 85.65(13) . .
