#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:05:42 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236395 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/66/7236659.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_7236659
loop_
_publ_author_name
'Mishra, Ruchika'
'Regar, Ramprasad'
'Singh, Varun'
'Panini, Piyush'
'Singhal, Rahul'
'Keshtov, M. L.'
'Sharma, Ganesh D.'
'Sankar, Jeyaraman'
_publ_section_title
;
 Modulation of the power conversion efficiency of organic solar cells via
 architectural variation of a promising non-fullerene acceptor
;
_journal_issue                   2
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              574
_journal_paper_doi               10.1039/C7TA08533H
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C46 H34 N2 O4 S2'
_chemical_formula_sum            'C46 H34 N2 O4 S2'
_chemical_formula_weight         742.87
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-08-21 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                91.005(3)
_cell_angle_beta                 102.408(4)
_cell_angle_gamma                98.557(2)
_cell_formula_units_Z            1
_cell_length_a                   7.2661(9)
_cell_length_b                   7.4190(9)
_cell_length_c                   16.444(2)
_cell_measurement_reflns_used    3608
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.55
_cell_measurement_theta_min      2.54
_cell_volume                     854.98(18)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14690
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.540
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3020
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0662P)²+0.8308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1535
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2047
_reflns_number_total             3020
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ta08533h2.cif
_cod_data_source_block           R23
_cod_original_cell_volume        854.99(18)
_cod_database_code               7236659
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.969
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2314(3) 0.7676(3) 0.76057(12) 0.0314(5) Uani 1 1 d . . . . .
O2 O 0.7523(3) 0.5084(3) 0.87956(12) 0.0366(6) Uani 1 1 d . . . . .
N1 N 0.9974(3) 0.6361(3) 0.82259(13) 0.0207(5) Uani 1 1 d . . . . .
C1 C 1.2401(4) 0.3684(4) 0.90013(18) 0.0287(7) Uani 1 1 d . . . . .
H1A H 1.1567 0.3182 0.9365 0.043 Uiso 1 1 calc R U . . .
H1B H 1.3549 0.3101 0.9101 0.043 Uiso 1 1 calc R U . . .
H1C H 1.1723 0.3449 0.8417 0.043 Uiso 1 1 calc R U . . .
C2 C 1.2967(4) 0.5728(4) 0.91885(17) 0.0227(7) Uani 1 1 d . . . . .
H2A H 1.3790 0.6229 0.8812 0.027 Uiso 1 1 calc R U . . .
H2B H 1.3722 0.5952 0.9768 0.027 Uiso 1 1 calc R U . . .
C3 C 1.1251(4) 0.6729(4) 0.90822(16) 0.0216(6) Uani 1 1 d . . . . .
H3 H 1.0483 0.6211 0.9484 0.026 Uiso 1 1 calc R U . . .
C4 C 1.1760(4) 0.8771(4) 0.92992(17) 0.0275(7) Uani 1 1 d . . . . .
H4A H 1.2674 0.9313 0.8969 0.033 Uiso 1 1 calc R U . . .
H4B H 1.0594 0.9341 0.9143 0.033 Uiso 1 1 calc R U . . .
C5 C 1.2626(4) 0.9195(4) 1.02117(18) 0.0311(7) Uani 1 1 d . . . . .
H5A H 1.1777 0.8572 1.0544 0.047 Uiso 1 1 calc R U . . .
H5B H 1.2798 1.0516 1.0332 0.047 Uiso 1 1 calc R U . . .
H5C H 1.3867 0.8774 1.0354 0.047 Uiso 1 1 calc R U . . .
C6 C 1.0676(4) 0.6906(4) 0.75324(17) 0.0224(6) Uani 1 1 d . . . . .
C7 C 0.9377(4) 0.6544(4) 0.66998(16) 0.0203(6) Uani 1 1 d . . . . .
C8 C 0.7478(4) 0.5686(4) 0.66085(16) 0.0182(6) Uani 1 1 d . . . . .
C9 C 0.6828(4) 0.5169(4) 0.73316(16) 0.0203(6) Uani 1 1 d . . . . .
C10 C 0.8092(4) 0.5512(4) 0.81725(17) 0.0233(7) Uani 1 1 d . . . . .
C11 C 0.4994(4) 0.4339(4) 0.72600(17) 0.0279(7) Uani 1 1 d . . . . .
H11 H 0.4563 0.3997 0.7750 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3723(4) 0.3977(4) 0.64803(17) 0.0269(7) Uani 1 1 d . . . . .
C13 C 0.6236(4) 0.5341(4) 0.58072(16) 0.0176(6) Uani 1 1 d . . . . .
C14 C 0.6951(4) 0.5886(4) 0.50885(16) 0.0190(6) Uani 1 1 d . . . . .
C16 C 1.0020(4) 0.7066(4) 0.60128(18) 0.0305(8) Uani 1 1 d . . . . .
H16 H 1.1298 0.7658 0.6072 0.037 Uiso 1 1 calc R U . A .
C17 C 0.4304(4) 0.4468(4) 0.57412(17) 0.0201(6) Uani 1 1 d . . . . .
C15 C 0.8839(4) 0.6750(4) 0.52207(18) 0.0317(8) Uani 1 1 d . . . A -1
H15 H 0.9337 0.7137 0.4753 0.038 Uiso 1 1 calc R U . A -1
C18A C 0.1901(6) 0.2896(6) 0.6544(2) 0.0167(10) Uani 0.627(3) 1 d . . P B -1
C19A C 0.0463(6) 0.2107(6) 0.6681(2) 0.0192(10) Uani 0.627(3) 1 d . . P B -1
C20A C -0.1343(7) 0.1164(8) 0.6810(4) 0.0339(5) Uani 0.627(3) 1 d D . P B -1
C21A C -0.1860(8) 0.0649(8) 0.7556(4) 0.0339(5) Uani 0.627(3) 1 d D . P B -1
H21A H -0.0999 0.0861 0.8084 0.041 Uiso 0.627(3) 1 calc R U P B -1
C22A C -0.3803(10) -0.0228(11) 0.7454(6) 0.0339(5) Uani 0.627(3) 1 d D . P B -1
H22A H -0.4403 -0.0653 0.7888 0.041 Uiso 0.627(3) 1 calc R U P B -1
C23A C -0.2850(8) 0.0690(7) 0.6121(4) 0.0339(5) Uani 0.627(3) 1 d D . P B -1
H23A H -0.2786 0.0923 0.5560 0.041 Uiso 0.627(3) 1 calc R U P B -1
S1A S -0.48331(19) -0.0371(2) 0.64265(10) 0.0339(5) Uani 0.627(3) 1 d D . P B
-1
C18B C 0.9775(11) 0.7683(12) 0.4552(5) 0.031(2) Uani 0.373(3) 1 d . . P B -2
C19B C 1.0725(12) 0.8295(11) 0.4143(5) 0.031(2) Uani 0.373(3) 1 d . . P B -2
C20B C -0.1835(18) 0.1009(13) 0.6455(6) 0.0393(9) Uani 0.373(3) 1 d D . P B -2
C21B C -0.3862(16) 0.0458(12) 0.6137(6) 0.0393(9) Uani 0.373(3) 1 d D . P B -2
H21B H -0.4517 0.0517 0.5574 0.047 Uiso 0.373(3) 1 calc R U P B -2
C22B C -0.4758(17) -0.0215(14) 0.6827(7) 0.0393(9) Uani 0.373(3) 1 d D . P B -2
H22B H -0.6083 -0.0616 0.6777 0.047 Uiso 0.373(3) 1 calc R U P B -2
C23B C -0.1353(15) 0.0681(13) 0.7319(6) 0.0393(9) Uani 0.373(3) 1 d D . P B -2
H23B H -0.0095 0.0935 0.7653 0.047 Uiso 0.373(3) 1 calc R U P B -2
S1B S -0.3173(4) -0.0165(4) 0.76613(17) 0.0393(9) Uani 0.373(3) 1 d D . P B -2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_3
C6 N1 C10 123.0(2) .
C6 N1 C3 119.5(2) .
C10 N1 C3 117.5(2) .
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
C1 C2 C3 112.7(2) .
C1 C2 H2A 109.0 .
C3 C2 H2A 109.0 .
C1 C2 H2B 109.0 .
C3 C2 H2B 109.0 .
H2A C2 H2B 107.8 .
N1 C3 C4 110.8(2) .
N1 C3 C2 111.9(2) .
C4 C3 C2 114.2(2) .
N1 C3 H3 106.5 .
C4 C3 H3 106.5 .
C2 C3 H3 106.5 .
C5 C4 C3 112.5(2) .
C5 C4 H4A 109.1 .
C3 C4 H4A 109.1 .
C5 C4 H4B 109.1 .
C3 C4 H4B 109.1 .
H4A C4 H4B 107.8 .
C4 C5 H5A 109.5 .
C4 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
C4 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
O1 C6 N1 121.0(2) .
O1 C6 C7 120.8(2) .
N1 C6 C7 118.2(2) .
C16 C7 C8 119.2(3) .
C16 C7 C6 119.5(2) .
C8 C7 C6 121.3(2) .
C7 C8 C9 118.4(2) .
C7 C8 C13 121.1(2) .
C9 C8 C13 120.5(2) .
C11 C9 C8 119.5(2) .
C11 C9 C10 118.9(2) .
C8 C9 C10 121.6(2) .
O2 C10 N1 121.0(2) .
O2 C10 C9 121.5(3) .
N1 C10 C9 117.6(2) .
C9 C11 C12 121.7(3) .
C9 C11 H11 119.2 .
C12 C11 H11 119.2 .
C11 C12 C17 120.9(3) .
C11 C12 C18A 112.2(3) .
C17 C12 C18A 126.5(3) .
C8 C13 C14 118.8(2) .
C8 C13 C17 119.3(2) .
C14 C13 C17 121.9(2) .
C15 C14 C13 117.4(2) .
C15 C14 C17 123.1(2) 2_666
C13 C14 C17 119.5(2) 2_666
C7 C16 C15 121.0(3) .
C7 C16 H16 119.5 .
C15 C16 H16 119.5 .
C12 C17 C13 118.0(2) .
C12 C17 C14 123.4(2) 2_666
C13 C17 C14 118.6(2) 2_666
C16 C15 C14 122.5(3) .
C16 C15 H15 118.8 .
C14 C15 H15 118.8 .
C19A C18A C12 172.7(4) .
C18A C19A C20A 177.2(5) .
C23A C20A C21A 112.0(5) .
C23A C20A C19A 118.9(6) .
C21A C20A C19A 129.2(5) .
C20A C21A C22A 114.2(6) .
C20A C21A H21A 122.9 .
C22A C21A H21A 122.9 .
C21A C22A S1A 108.2(6) .
C21A C22A H22A 125.9 .
S1A C22A H22A 125.9 .
C20A C23A S1A 110.4(4) .
C20A C23A H23A 124.8 .
S1A C23A H23A 124.8 .
C22A S1A C23A 95.2(3) .
C23B C20B C21B 109.7(8) .
C20B C21B C22B 109.3(9) .
C20B C21B H21B 125.4 .
C22B C21B H21B 125.4 .
C21B C22B S1B 109.9(8) .
C21B C22B H22B 125.0 .
S1B C22B H22B 125.0 .
C20B C23B S1B 112.1(8) .
C20B C23B H23B 124.0 .
S1B C23B H23B 124.0 .
C22B S1B C23B 99.0(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.221(3) .
O2 C10 1.215(3) .
N1 C6 1.389(3) .
N1 C10 1.402(3) .
N1 C3 1.506(3) .
C1 C2 1.519(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.525(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.522(4) .
C3 H3 1.0000 .
C4 C5 1.505(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C7 1.481(4) .
C7 C16 1.354(4) .
C7 C8 1.406(4) .
C8 C9 1.410(4) .
C8 C13 1.423(4) .
C9 C11 1.362(4) .
C9 C10 1.481(4) .
C11 C12 1.405(4) .
C11 H11 0.9500 .
C12 C17 1.406(4) .
C12 C18A 1.468(5) .
C13 C14 1.431(4) .
C13 C17 1.436(4) .
C14 C15 1.395(4) .
C14 C17 1.464(4) 2_666
C16 C15 1.392(4) .
C16 H16 0.9500 .
C17 C14 1.464(4) 2_666
C15 H15 0.9500 .
C18A C19A 1.187(6) .
C19A C20A 1.452(7) .
C20A C23A 1.395(7) .
C20A C21A 1.400(8) .
C21A C22A 1.437(8) .
C21A H21A 0.9500 .
C22A S1A 1.688(8) .
C22A H22A 0.9500 .
C23A S1A 1.714(6) .
C23A H23A 0.9500 .
C18B C19B 1.118(11) .
C20B C23B 1.423(11) .
C20B C21B 1.447(12) .
C21B C22B 1.484(11) .
C21B H21B 0.9500 .
C22B S1B 1.586(12) .
C22B H22B 0.9500 .
C23B S1B 1.595(9) .
C23B H23B 0.9500 .
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
C6 N1 C3 C4 65.8(3) . .
C10 N1 C3 C4 -112.6(3) . .
C6 N1 C3 C2 -63.0(3) . .
C10 N1 C3 C2 118.6(3) . .
C1 C2 C3 N1 -55.5(3) . .
C1 C2 C3 C4 177.6(2) . .
N1 C3 C4 C5 166.2(2) . .
C2 C3 C4 C5 -66.3(3) . .
C10 N1 C6 O1 178.5(3) . .
C3 N1 C6 O1 0.2(4) . .
C10 N1 C6 C7 -0.9(4) . .
C3 N1 C6 C7 -179.2(2) . .
O1 C6 C7 C16 0.4(4) . .
N1 C6 C7 C16 179.8(3) . .
O1 C6 C7 C8 -178.9(3) . .
N1 C6 C7 C8 0.5(4) . .
C16 C7 C8 C9 -179.4(3) . .
C6 C7 C8 C9 -0.1(4) . .
C16 C7 C8 C13 0.7(4) . .
C6 C7 C8 C13 -179.9(2) . .
C7 C8 C9 C11 179.8(3) . .
C13 C8 C9 C11 -0.3(4) . .
C7 C8 C9 C10 0.1(4) . .
C13 C8 C9 C10 180.0(2) . .
C6 N1 C10 O2 -178.7(3) . .
C3 N1 C10 O2 -0.4(4) . .
C6 N1 C10 C9 0.9(4) . .
C3 N1 C10 C9 179.3(2) . .
C11 C9 C10 O2 -0.6(4) . .
C8 C9 C10 O2 179.1(3) . .
C11 C9 C10 N1 179.7(3) . .
C8 C9 C10 N1 -0.5(4) . .
C8 C9 C11 C12 0.2(4) . .
C10 C9 C11 C12 179.9(3) . .
C9 C11 C12 C17 -0.2(5) . .
C9 C11 C12 C18A 173.5(3) . .
C7 C8 C13 C14 -0.1(4) . .
C9 C8 C13 C14 -179.9(2) . .
C7 C8 C13 C17 -179.8(2) . .
C9 C8 C13 C17 0.4(4) . .
C8 C13 C14 C15 -0.6(4) . .
C17 C13 C14 C15 179.0(3) . .
C8 C13 C14 C17 179.7(2) . 2_666
C17 C13 C14 C17 -0.7(4) . 2_666
C8 C7 C16 C15 -0.6(5) . .
C6 C7 C16 C15 -180.0(3) . .
C11 C12 C17 C13 0.3(4) . .
C18A C12 C17 C13 -172.5(3) . .
C11 C12 C17 C14 179.6(3) . 2_666
C18A C12 C17 C14 6.8(5) . 2_666
C8 C13 C17 C12 -0.4(4) . .
C14 C13 C17 C12 179.9(2) . .
C8 C13 C17 C14 -179.7(2) . 2_666
C14 C13 C17 C14 0.7(4) . 2_666
C7 C16 C15 C14 -0.1(5) . .
C13 C14 C15 C16 0.8(5) . .
C17 C14 C15 C16 -179.6(3) 2_666 .
C23A C20A C21A C22A -0.5(7) . .
C19A C20A C21A C22A 178.3(6) . .
C20A C21A C22A S1A 0.8(7) . .
C21A C20A C23A S1A -0.1(6) . .
C19A C20A C23A S1A -179.0(4) . .
C21A C22A S1A C23A -0.7(6) . .
C20A C23A S1A C22A 0.5(5) . .
C23B C20B C21B C22B 1.6(11) . .
C20B C21B C22B S1B -2.2(10) . .
C21B C20B C23B S1B -0.4(10) . .
C21B C22B S1B C23B 1.8(8) . .
C20B C23B S1B C22B -0.8(8) . .
