#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/16/4001644.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_4001644
loop_
_publ_author_name
'Kim, Chunki'
'Liu, Jianhua'
'Lin, Jason'
'Tamayo, Arnold B.'
'Walker, Bright'
'Wu, Guang'
'Nguyen, Thuc-Quyen'
_publ_section_title
;
 Influence of Structural Variation on the Solid-State Properties of
 Diketopyrrolopyrrole-Based Oligophenylenethiophenes: Single-Crystal
 Structures, Thermal Properties, Optical Bandgaps, Energy Levels, Film
 Morphology, and Hole Mobility
;
_journal_issue                   10
_journal_name_full               'Chemistry of Materials'
_journal_page_first              1699
_journal_paper_doi               10.1021/cm202852f
_journal_volume                  24
_journal_year                    2012
_chemical_formula_sum            'C58 H68 N2 O2 S4'
_chemical_formula_weight         953.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.891(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.2356(12)
_cell_length_b                   14.3381(10)
_cell_length_c                   9.8764(6)
_cell_measurement_temperature    100(2)
_cell_volume                     2563.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Kappa APex II'
_diffrn_measurement_method       'Omega scan'
_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  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0702
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14937
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         1.12
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         6519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0540
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                4198
_reflns_number_total             6519
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm202852f_si_003.cif
_cod_data_source_block           C6PT2C6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/C
_cod_database_code               4001644
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
S1 S 0.30791(3) 0.46308(5) 0.23754(6) 0.02384(16) Uani 1 1 d .
S2 S 0.28648(3) 0.32730(4) 0.62681(6) 0.02318(16) Uani 1 1 d .
O1 O 0.46398(9) 0.68774(12) -0.61270(16) 0.0233(4) Uani 1 1 d .
N1 N 0.43578(10) 0.60695(14) -0.42250(19) 0.0189(4) Uani 1 1 d .
C13 C 0.32007(12) 0.39163(16) 0.3790(2) 0.0197(5) Uani 1 1 d .
C4 C 0.42911(12) 0.49228(17) -0.2304(2) 0.0191(5) Uani 1 1 d .
C11 C 0.40610(12) 0.33530(17) 0.2444(2) 0.0199(5) Uani 1 1 d .
H11 H 0.4446 0.2958 0.2213 0.024 Uiso 1 1 calc R
C17 C 0.21774(12) 0.38041(18) 0.7047(2) 0.0235(5) Uani 1 1 d .
C12 C 0.37440(12) 0.32780(17) 0.3674(2) 0.0202(5) Uani 1 1 d .
H12 H 0.3894 0.2827 0.4356 0.024 Uiso 1 1 calc R
C6 C 0.45392(12) 0.39608(16) -0.0279(2) 0.0190(4) Uani 1 1 d .
H6 H 0.4837 0.3506 0.0225 0.023 Uiso 1 1 calc R
C9 C 0.36636(12) 0.52604(18) -0.1790(2) 0.0220(5) Uani 1 1 d .
H9 H 0.3353 0.5695 -0.2310 0.026 Uiso 1 1 calc R
C16 C 0.18876(13) 0.45378(19) 0.6285(3) 0.0286(6) Uani 1 1 d .
H16 H 0.1506 0.4925 0.6546 0.034 Uiso 1 1 calc R
C2 C 0.45244(12) 0.52101(16) -0.3597(2) 0.0189(4) Uani 1 1 d .
C5 C 0.47170(12) 0.42462(16) -0.1525(2) 0.0196(5) Uani 1 1 d .
H5 H 0.5135 0.3983 -0.1871 0.024 Uiso 1 1 calc R
C10 C 0.37570(12) 0.40545(17) 0.1616(2) 0.0191(5) Uani 1 1 d .
C7 C 0.39267(11) 0.43297(17) 0.0260(2) 0.0193(5) Uani 1 1 d .
C8 C 0.34867(12) 0.49728(18) -0.0538(2) 0.0236(5) Uani 1 1 d .
H8 H 0.3057 0.5216 -0.0208 0.028 Uiso 1 1 calc R
C15 C 0.22125(13) 0.46668(19) 0.5062(3) 0.0273(5) Uani 1 1 d .
H15 H 0.2070 0.5147 0.4421 0.033 Uiso 1 1 calc R
C3 C 0.49524(12) 0.47266(16) -0.4421(2) 0.0192(5) Uani 1 1 d .
C14 C 0.27518(12) 0.40291(17) 0.4902(2) 0.0216(5) Uani 1 1 d .
C1 C 0.46885(12) 0.61571(16) -0.5447(2) 0.0194(5) Uani 1 1 d .
C18 C 0.20056(13) 0.34265(19) 0.8387(2) 0.0258(5) Uani 1 1 d .
H18A H 0.2470 0.3391 0.9017 0.031 Uiso 1 1 calc R
H18B H 0.1814 0.2783 0.8246 0.031 Uiso 1 1 calc R
C20 C 0.13001(14) 0.3582(2) 1.0420(3) 0.0299(6) Uani 1 1 d .
H20A H 0.1778 0.3462 1.0980 0.036 Uiso 1 1 calc R
H20B H 0.1046 0.2975 1.0251 0.036 Uiso 1 1 calc R
C19 C 0.14473(14) 0.3998(2) 0.9061(3) 0.0311(6) Uani 1 1 d .
H19A H 0.0978 0.4030 0.8444 0.037 Uiso 1 1 calc R
H19B H 0.1635 0.4642 0.9210 0.037 Uiso 1 1 calc R
C21 C 0.08312(16) 0.4208(2) 1.1216(3) 0.0375(7) Uani 1 1 d .
H21A H 0.1080 0.4820 1.1364 0.045 Uiso 1 1 calc R
H21B H 0.0349 0.4315 1.0662 0.045 Uiso 1 1 calc R
C22 C 0.06958(17) 0.3809(3) 1.2587(3) 0.0423(7) Uani 1 1 d .
H22A H 0.1176 0.3708 1.3148 0.051 Uiso 1 1 calc R
H22B H 0.0449 0.3196 1.2444 0.051 Uiso 1 1 calc R
C23 C 0.0220(2) 0.4447(3) 1.3357(4) 0.0664(12) Uani 1 1 d .
H23A H 0.0442 0.5071 1.3436 0.100 Uiso 1 1 calc R
H23B H 0.0190 0.4193 1.4270 0.100 Uiso 1 1 calc R
H23C H -0.0277 0.4489 1.2859 0.100 Uiso 1 1 calc R
C24 C 0.40152(13) 0.68852(17) -0.3694(2) 0.0218(5) Uani 1 1 d .
H24A H 0.4306 0.7445 -0.3873 0.026 Uiso 1 1 calc R
H24B H 0.4027 0.6821 -0.2694 0.026 Uiso 1 1 calc R
C25 C 0.32196(13) 0.70261(18) -0.4322(3) 0.0258(5) Uani 1 1 d .
H25A H 0.3209 0.7159 -0.5308 0.031 Uiso 1 1 calc R
H25B H 0.2936 0.6446 -0.4224 0.031 Uiso 1 1 calc R
C26 C 0.28627(16) 0.7820(2) -0.3645(3) 0.0452(8) Uani 1 1 d .
H26A H 0.3200 0.8364 -0.3597 0.054 Uiso 1 1 calc R
H26B H 0.2805 0.7635 -0.2698 0.054 Uiso 1 1 calc R
C27 C 0.21136(18) 0.8121(3) -0.4349(4) 0.0566(10) Uani 1 1 d .
H27A H 0.1944 0.8671 -0.3868 0.068 Uiso 1 1 calc R
H27B H 0.2170 0.8313 -0.5294 0.068 Uiso 1 1 calc R
C28 C 0.1544(2) 0.7391(3) -0.4395(7) 0.0949(18) Uani 1 1 d .
H28A H 0.1532 0.7136 -0.3467 0.114 Uiso 1 1 calc R
H28B H 0.1675 0.6876 -0.4989 0.114 Uiso 1 1 calc R
C29 C 0.0775(3) 0.7760(5) -0.4933(10) 0.160(4) Uani 1 1 d .
H29A H 0.0617 0.8217 -0.4289 0.241 Uiso 1 1 calc R
H29B H 0.0423 0.7241 -0.5033 0.241 Uiso 1 1 calc R
H29C H 0.0793 0.8058 -0.5821 0.241 Uiso 1 1 calc R
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'
S S 0.1246 0.1234 '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
C13 S1 C10 92.21(11) . .
C14 S2 C17 92.66(12) . .
C2 N1 C1 111.33(19) . .
C2 N1 C24 129.07(18) . .
C1 N1 C24 118.74(19) . .
C12 C13 C14 128.2(2) . .
C12 C13 S1 110.76(17) . .
C14 C13 S1 121.05(18) . .
C9 C4 C5 117.5(2) . .
C9 C4 C2 124.2(2) . .
C5 C4 C2 118.3(2) . .
C10 C11 C12 113.0(2) . .
C16 C17 C18 131.2(2) . .
C16 C17 S2 110.41(17) . .
C18 C17 S2 118.36(19) . .
C13 C12 C11 113.5(2) . .
C5 C6 C7 120.9(2) . .
C8 C9 C4 120.9(2) . .
C17 C16 C15 113.4(2) . .
C3 C2 N1 106.88(19) . .
C3 C2 C4 128.4(2) . .
N1 C2 C4 124.7(2) . .
C6 C5 C4 121.3(2) . .
C11 C10 C7 128.9(2) . .
C11 C10 S1 110.52(16) . .
C7 C10 S1 120.52(17) . .
C6 C7 C8 117.7(2) . .
C6 C7 C10 120.8(2) . .
C8 C7 C10 121.5(2) . .
C9 C8 C7 121.4(2) . .
C14 C15 C16 113.0(2) . .
C2 C3 C3 109.3(3) . 3_664
C2 C3 C1 142.3(2) . 3_664
C3 C3 C1 108.2(2) 3_664 3_664
C15 C14 C13 129.8(2) . .
C15 C14 S2 110.55(18) . .
C13 C14 S2 119.69(18) . .
O1 C1 N1 122.0(2) . .
O1 C1 C3 133.9(2) . 3_664
N1 C1 C3 104.12(19) . 3_664
C17 C18 C19 114.4(2) . .
C19 C20 C21 113.2(2) . .
C18 C19 C20 111.8(2) . .
C22 C21 C20 113.6(2) . .
C21 C22 C23 112.5(3) . .
N1 C24 C25 112.95(19) . .
C26 C25 C24 111.1(2) . .
C25 C26 C27 115.0(3) . .
C28 C27 C26 113.9(3) . .
C27 C28 C29 112.2(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C13 1.726(2) .
S1 C10 1.731(2) .
S2 C14 1.724(2) .
S2 C17 1.725(2) .
O1 C1 1.229(3) .
N1 C2 1.396(3) .
N1 C1 1.418(3) .
N1 C24 1.453(3) .
C13 C12 1.364(3) .
C13 C14 1.455(3) .
C4 C9 1.393(3) .
C4 C5 1.412(3) .
C4 C2 1.453(3) .
C11 C10 1.371(3) .
C11 C12 1.411(3) .
C17 C16 1.363(4) .
C17 C18 1.498(3) .
C6 C5 1.372(3) .
C6 C7 1.398(3) .
C9 C8 1.379(3) .
C16 C15 1.420(3) .
C2 C3 1.380(3) .
C10 C7 1.464(3) .
C7 C8 1.401(3) .
C15 C14 1.366(3) .
C3 C3 1.415(4) 3_664
C3 C1 1.439(3) 3_664
C1 C3 1.439(3) 3_664
C18 C19 1.521(3) .
C20 C19 1.522(4) .
C20 C21 1.522(4) .
C21 C22 1.517(4) .
C22 C23 1.525(4) .
C24 C25 1.521(3) .
C25 C26 1.508(4) .
C26 C27 1.519(4) .
C27 C28 1.472(6) .
C28 C29 1.532(6) .
