#------------------------------------------------------------------------------
#$Date: 2019-10-01 10:17:20 +0300 (Tue, 01 Oct 2019) $
#$Revision: 218951 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/42/7234254.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_7234254
loop_
_publ_author_name
'Yue Jiang'
'Clement Cabanetos'
'Magali Allain'
'Ping Liu'
'Jean Roncali'
_publ_section_title
;
 Manipulation of the band gap and efficiency of a minimalist push-pull
 molecular donor for organic solar cells
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              5145
_journal_page_last               5151
_journal_paper_doi               10.1039/C5TC00913H
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C21 H15 N3 S1'
_chemical_formula_sum            'C21 H15 N3 S'
_chemical_formula_weight         341.42
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                82.547(6)
_cell_angle_beta                 84.108(6)
_cell_angle_gamma                87.123(5)
_cell_formula_units_Z            2
_cell_length_a                   5.7003(4)
_cell_length_b                   8.7382(5)
_cell_length_c                   17.506(1)
_cell_measurement_reflns_used    7815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      4.00
_cell_volume                     859.44(9)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND 3.2i (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30819
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         4
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0381P)²+0.2550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                2704
_reflns_number_total             3941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-5145.cif
_cod_data_source_block           sad
_cod_database_code               7234254
loop_
_symmetry_equiv_pos_as_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C -0.1038(4) 0.6939(3) 0.03822(13) 0.0700(6) Uani 1 d . . .
H1 H -0.2353 0.64 0.0607 0.084 Uiso 1 calc R . .
C2 C -0.0685(5) 0.7298(3) -0.04204(14) 0.0834(8) Uani 1 d . . .
H2 H -0.1786 0.7012 -0.0728 0.1 Uiso 1 calc R . .
C3 C 0.1243(5) 0.8058(3) -0.07565(12) 0.0649(6) Uani 1 d . . .
H3 H 0.1478 0.8284 -0.1292 0.078 Uiso 1 calc R . .
C4 C 0.2828(4) 0.8488(3) -0.03044(13) 0.0731(7) Uani 1 d . . .
H4 H 0.4163 0.9002 -0.0532 0.088 Uiso 1 calc R . .
C5 C 0.2469(4) 0.8165(3) 0.04932(11) 0.0614(6) Uani 1 d . . .
H5 H 0.3548 0.8487 0.0798 0.074 Uiso 1 calc R . .
C6 C 0.0551(3) 0.73808(19) 0.08381(9) 0.0395(4) Uani 1 d . . .
C7 C -0.1772(3) 0.8015(2) 0.20308(11) 0.0493(5) Uani 1 d . . .
H7A H -0.2643 0.7371 0.2438 0.074 Uiso 1 calc R . .
H7B H -0.2808 0.8438 0.1651 0.074 Uiso 1 calc R . .
H7C H -0.1116 0.884 0.2243 0.074 Uiso 1 calc R . .
C8 C 0.1747(3) 0.62660(19) 0.21046(9) 0.0378(4) Uani 1 d . . .
C9 C 0.1664(3) 0.6300(2) 0.29112(10) 0.0421(4) Uani 1 d . . .
H9 H 0.05 0.6903 0.3155 0.05 Uiso 1 calc R . .
C10 C 0.3279(3) 0.5454(2) 0.33401(10) 0.0421(4) Uani 1 d . . .
H10 H 0.3185 0.5505 0.387 0.051 Uiso 1 calc R . .
C11 C 0.5066(3) 0.45163(19) 0.30069(9) 0.0378(4) Uani 1 d . . .
C12 C 0.5109(3) 0.44627(19) 0.22085(9) 0.0406(4) Uani 1 d . . .
H12 H 0.6255 0.3842 0.1968 0.049 Uiso 1 calc R . .
C13 C 0.3511(3) 0.53002(19) 0.17724(9) 0.0402(4) Uani 1 d . . .
H13 H 0.3593 0.5229 0.1245 0.048 Uiso 1 calc R . .
C14 C 0.6799(3) 0.36675(19) 0.34695(9) 0.0410(4) Uani 1 d . . .
C15 C 0.7009(4) 0.3628(3) 0.42511(11) 0.0634(6) Uani 1 d . . .
H15 H 0.5988 0.4179 0.4574 0.076 Uiso 1 calc R . .
C16 C 0.8879(4) 0.2694(3) 0.45109(11) 0.0621(6) Uani 1 d . . .
H16 H 0.923 0.2568 0.5023 0.074 Uiso 1 calc R . .
C17 C 1.0171(3) 0.1969(2) 0.39410(9) 0.0426(4) Uani 1 d . . .
C18 C 1.2109(3) 0.0938(2) 0.40685(10) 0.0433(4) Uani 1 d . . .
H18 H 1.2455 0.0754 0.4581 0.052 Uiso 1 calc R . .
C19 C 1.3566(3) 0.0164(2) 0.35709(9) 0.0403(4) Uani 1 d . . .
C20 C 1.5424(3) -0.0852(2) 0.38535(10) 0.0476(5) Uani 1 d . . .
C21 C 1.3407(3) 0.0325(2) 0.27526(10) 0.0423(4) Uani 1 d . . .
N1 N 0.0133(3) 0.70946(18) 0.16666(8) 0.0459(4) Uani 1 d . . .
N2 N 1.3313(3) 0.0452(2) 0.20983(9) 0.0634(5) Uani 1 d . . .
N3 N 1.6896(3) -0.1659(2) 0.40879(10) 0.0685(5) Uani 1 d . . .
S1 S 0.89872(8) 0.25004(5) 0.30623(2) 0.03936(14) Uani 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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'
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
C6 C1 C2 119.9(2) . .
C6 C1 H1 120 . .
C2 C1 H1 120 . .
C3 C2 C1 120.7(2) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C4 119.4(2) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C3 C4 C5 120.3(2) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C6 C5 C4 120.80(19) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C1 118.82(18) . .
C5 C6 N1 120.78(16) . .
C1 C6 N1 120.32(17) . .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C13 121.40(15) . .
N1 C8 C9 121.71(15) . .
C13 C8 C9 116.86(15) . .
C10 C9 C8 120.86(16) . .
C10 C9 H9 119.6 . .
C8 C9 H9 119.6 . .
C9 C10 C11 122.29(16) . .
C9 C10 H10 118.9 . .
C11 C10 H10 118.9 . .
C12 C11 C10 116.58(15) . .
C12 C11 C14 122.16(15) . .
C10 C11 C14 121.25(15) . .
C13 C12 C11 121.83(16) . .
C13 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C12 C13 C8 121.55(15) . .
C12 C13 H13 119.2 . .
C8 C13 H13 119.2 . .
C15 C14 C11 128.78(16) . .
C15 C14 S1 109.86(13) . .
C11 C14 S1 121.36(12) . .
C14 C15 C16 114.00(17) . .
C14 C15 H15 123 . .
C16 C15 H15 123 . .
C17 C16 C15 113.96(16) . .
C17 C16 H16 123 . .
C15 C16 H16 123 . .
C16 C17 C18 124.32(16) . .
C16 C17 S1 109.46(13) . .
C18 C17 S1 126.21(13) . .
C19 C18 C17 131.10(16) . .
C19 C18 H18 114.5 . .
C17 C18 H18 114.5 . .
C18 C19 C21 123.69(15) . .
C18 C19 C20 120.15(15) . .
C21 C19 C20 116.14(15) . .
N3 C20 C19 179.18(19) . .
N2 C21 C19 179.1(2) . .
C8 N1 C6 121.37(14) . .
C8 N1 C7 120.51(14) . .
C6 N1 C7 116.58(14) . .
C14 S1 C17 92.71(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.367(3) .
C1 C2 1.395(3) .
C1 H1 0.93 .
C2 C3 1.354(3) .
C2 H2 0.93 .
C3 C4 1.357(3) .
C3 H3 0.93 .
C4 C5 1.384(3) .
C4 H4 0.93 .
C5 C6 1.365(3) .
C5 H5 0.93 .
C6 N1 1.436(2) .
C7 N1 1.461(2) .
C7 H7A 0.96 .
C7 H7B 0.96 .
C7 H7C 0.96 .
C8 N1 1.375(2) .
C8 C13 1.408(2) .
C8 C9 1.412(2) .
C9 C10 1.374(2) .
C9 H9 0.93 .
C10 C11 1.403(2) .
C10 H10 0.93 .
C11 C12 1.402(2) .
C11 C14 1.455(2) .
C12 C13 1.371(2) .
C12 H12 0.93 .
C13 H13 0.93 .
C14 C15 1.382(2) .
C14 S1 1.7269(17) .
C15 C16 1.387(3) .
C15 H15 0.93 .
C16 C17 1.380(3) .
C16 H16 0.93 .
C17 C18 1.407(2) .
C17 S1 1.7416(16) .
C18 C19 1.362(2) .
C18 H18 0.93 .
C19 C21 1.433(2) .
C19 C20 1.433(3) .
C20 N3 1.143(2) .
C21 N2 1.143(2) .
