#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/69/4106912.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_4106912
loop_
_publ_author_name
'Li-Yen Lin'
'Yi-Hong Chen'
'Zheng-Yu Huang'
'Hao-Wu Lin'
'Shu-Hua Chou'
'Francis Lin'
'Chang-Wen Chen'
'Yi-Hung Liu'
'Ken-Tsung Wong'
_publ_section_title
;
 A Low-Energy-Gap Organic Dye for High-Performance Small-Molecule Organic
 Solar Cells
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15822
_journal_page_last               15825
_journal_paper_doi               10.1021/ja205126t
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C28 H19 N5 S2'
_chemical_formula_weight         489.60
_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                 92.984(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6787(2)
_cell_length_b                   16.9340(4)
_cell_length_c                   18.3591(4)
_cell_measurement_reflns_used    6803
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      76.8630
_cell_measurement_theta_min      3.5501
_cell_volume                     2384.02(10)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) 
(compiled Jan 20 2011,15:58:25) 
empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) 
(compiled Jan 20 2011,15:58:25) 
empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) 
(compiled Jan 20 2011,15:58:25) 
empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14007
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    2.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) 
(compiled Jan 20 2011,15:58:25) 
empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.004
_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          0.1272
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                3910
_reflns_number_total             4346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja205126t_si_001.cif
_cod_data_source_block           ic14908
_cod_database_code               4106912
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 0.31247(6) 0.96784(3) 0.65158(2) 0.03368(16) Uani 1 1 d .
S2 S 0.06028(5) 0.90365(2) 0.32556(2) 0.02981(16) Uani 1 1 d .
N1 N 0.22636(17) 0.93228(8) 0.57657(7) 0.0289(3) Uani 1 1 d .
N2 N 0.38339(19) 1.05220(9) 0.62403(8) 0.0323(3) Uani 1 1 d .
N3 N 0.6794(3) 1.36752(11) 0.57116(13) 0.0567(5) Uani 1 1 d .
N4 N 0.5936(2) 1.25383(11) 0.36151(10) 0.0480(4) Uani 1 1 d .
N5 N -0.1120(2) 0.77346(8) 0.27583(8) 0.0352(3) Uani 1 1 d .
C1 C 0.25019(19) 0.98659(9) 0.52491(9) 0.0244(3) Uani 1 1 d .
C2 C 0.34061(19) 1.05600(10) 0.55217(9) 0.0273(3) Uani 1 1 d .
C3 C 0.3803(2) 1.12007(9) 0.50490(9) 0.0277(3) Uani 1 1 d .
C4 C 0.3211(2) 1.11157(10) 0.43233(9) 0.0291(3) Uani 1 1 d .
H4A H 0.3416 1.1524 0.4000 0.035 Uiso 1 1 calc R
C5 C 0.2327(2) 1.04475(10) 0.40575(9) 0.0275(3) Uani 1 1 d .
H5A H 0.1967 1.0435 0.3566 0.033 Uiso 1 1 calc R
C6 C 0.19513(19) 0.97972(9) 0.44887(9) 0.0247(3) Uani 1 1 d .
C7 C 0.1077(2) 0.91093(9) 0.41972(8) 0.0249(3) Uani 1 1 d .
C8 C 0.0465(2) 0.84471(9) 0.45419(9) 0.0277(3) Uani 1 1 d .
H8A H 0.0602 0.8371 0.5043 0.033 Uiso 1 1 calc R
C9 C -0.0377(2) 0.79004(9) 0.40738(9) 0.0290(3) Uani 1 1 d .
H9A H -0.0851 0.7429 0.4232 0.035 Uiso 1 1 calc R
C10 C -0.0432(2) 0.81354(9) 0.33498(9) 0.0282(3) Uani 1 1 d .
C11 C 0.4683(2) 1.18875(10) 0.53528(10) 0.0325(4) Uani 1 1 d .
H11A H 0.4722 1.1927 0.5859 0.039 Uiso 1 1 calc R
C12 C 0.5460(2) 1.24829(10) 0.49981(11) 0.0337(4) Uani 1 1 d .
C13 C 0.6204(2) 1.31441(11) 0.54037(12) 0.0409(4) Uani 1 1 d .
C14 C 0.5695(2) 1.25108(10) 0.42292(11) 0.0358(4) Uani 1 1 d .
C15 C -0.1557(2) 0.69174(9) 0.28440(8) 0.0294(3) Uani 1 1 d .
C16 C -0.3290(2) 0.66851(10) 0.28153(9) 0.0338(4) Uani 1 1 d .
H16A H -0.4170 0.7051 0.2708 0.041 Uiso 1 1 calc R
C17 C -0.3702(2) 0.59022(10) 0.29473(10) 0.0340(4) Uani 1 1 d .
H17A H -0.4866 0.5748 0.2929 0.041 Uiso 1 1 calc R
C18 C -0.2415(2) 0.53434(9) 0.31057(9) 0.0301(4) Uani 1 1 d .
C19 C -0.0684(2) 0.55847(10) 0.31158(9) 0.0323(4) Uani 1 1 d .
H19A H 0.0197 0.5216 0.3209 0.039 Uiso 1 1 calc R
C20 C -0.0248(2) 0.63658(10) 0.29898(9) 0.0314(4) Uani 1 1 d .
H20A H 0.0916 0.6519 0.3003 0.038 Uiso 1 1 calc R
C21 C -0.2871(3) 0.45036(11) 0.32944(11) 0.0409(4) Uani 1 1 d .
H21A H -0.1820 0.4205 0.3388 0.061 Uiso 1 1 calc R
H21B H -0.3543 0.4271 0.2894 0.061 Uiso 1 1 calc R
H21C H -0.3542 0.4501 0.3721 0.061 Uiso 1 1 calc R
C22 C -0.1337(2) 0.80953(9) 0.20568(9) 0.0297(3) Uani 1 1 d .
C23 C -0.2408(2) 0.87498(10) 0.19554(10) 0.0319(4) Uani 1 1 d .
H23A H -0.3016 0.8946 0.2341 0.038 Uiso 1 1 calc R
C24 C -0.2569(2) 0.91110(10) 0.12762(10) 0.0336(4) Uani 1 1 d .
H24A H -0.3275 0.9554 0.1213 0.040 Uiso 1 1 calc R
C25 C -0.1690(3) 0.88208(11) 0.06867(10) 0.0352(4) Uani 1 1 d .
C26 C -0.0635(3) 0.81591(11) 0.08016(10) 0.0416(4) Uani 1 1 d .
H26A H -0.0035 0.7957 0.0416 0.050 Uiso 1 1 calc R
C27 C -0.0459(3) 0.77941(11) 0.14761(10) 0.0376(4) Uani 1 1 d .
H27A H 0.0245 0.7350 0.1540 0.045 Uiso 1 1 calc R
C28 C -0.1855(3) 0.92177(14) -0.00473(11) 0.0511(5) Uani 1 1 d .
H28B H -0.1162 0.8939 -0.0384 0.077 Uiso 1 1 calc R
H28C H -0.1453 0.9753 -0.0003 0.077 Uiso 1 1 calc R
H28D H -0.3054 0.9214 -0.0224 0.077 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 0.0181 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'
S S 0.3331 0.5567 '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
N1 S1 N2 101.09(8)
C10 S2 C7 92.09(8)
C1 N1 S1 106.43(11)
C2 N2 S1 106.24(12)
C10 N5 C22 121.86(14)
C10 N5 C15 118.43(14)
C22 N5 C15 119.65(13)
N1 C1 C2 113.25(14)
N1 C1 C6 125.85(14)
C2 C1 C6 120.90(14)
N2 C2 C1 112.99(15)
N2 C2 C3 125.59(15)
C1 C2 C3 121.41(15)
C4 C3 C11 125.18(16)
C4 C3 C2 115.62(14)
C11 C3 C2 119.12(15)
C3 C4 C5 123.18(15)
C6 C5 C4 123.58(15)
C5 C6 C7 122.41(15)
C5 C6 C1 115.27(14)
C7 C6 C1 122.33(14)
C8 C7 C6 130.69(15)
C8 C7 S2 109.66(12)
C6 C7 S2 119.64(12)
C7 C8 C9 114.41(14)
C10 C9 C8 112.90(14)
N5 C10 C9 127.73(15)
N5 C10 S2 121.30(13)
C9 C10 S2 110.93(12)
C12 C11 C3 128.54(17)
C11 C12 C14 125.37(16)
C11 C12 C13 120.04(18)
C14 C12 C13 114.53(16)
N3 C13 C12 178.6(2)
N4 C14 C12 177.96(19)
C20 C15 C16 120.03(15)
C20 C15 N5 119.93(16)
C16 C15 N5 119.97(16)
C17 C16 C15 119.46(16)
C16 C17 C18 121.46(16)
C19 C18 C17 118.19(15)
C19 C18 C21 120.48(16)
C17 C18 C21 121.28(16)
C20 C19 C18 121.14(15)
C19 C20 C15 119.70(16)
C27 C22 C23 119.94(16)
C27 C22 N5 119.79(16)
C23 C22 N5 120.27(16)
C24 C23 C22 119.81(16)
C23 C24 C25 121.17(17)
C26 C25 C24 117.86(16)
C26 C25 C28 121.08(19)
C24 C25 C28 121.05(18)
C25 C26 C27 121.61(18)
C22 C27 C26 119.61(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N1 1.6128(14)
S1 N2 1.6192(16)
S2 C10 1.7332(16)
S2 C7 1.7522(15)
N1 C1 1.341(2)
N2 C2 1.344(2)
N3 C13 1.143(3)
N4 C14 1.153(3)
N5 C10 1.364(2)
N5 C22 1.427(2)
N5 C15 1.435(2)
C1 C2 1.441(2)
C1 C6 1.442(2)
C2 C3 1.432(2)
C3 C4 1.393(2)
C3 C11 1.443(2)
C4 C5 1.395(2)
C5 C6 1.395(2)
C6 C7 1.434(2)
C7 C8 1.382(2)
C8 C9 1.399(2)
C9 C10 1.386(2)
C11 C12 1.356(3)
C12 C14 1.433(3)
C12 C13 1.446(2)
C15 C20 1.388(2)
C15 C16 1.386(3)
C16 C17 1.387(3)
C17 C18 1.388(3)
C18 C19 1.389(3)
C18 C21 1.509(2)
C19 C20 1.387(2)
C22 C27 1.388(3)
C22 C23 1.386(2)
C23 C24 1.389(2)
C24 C25 1.394(3)
C25 C26 1.392(3)
C25 C28 1.505(2)
C26 C27 1.384(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660276
