#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:17:23 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236452 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/67/7236705.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_7236705
loop_
_publ_author_name
'Li, Xiangchun'
'Wang, Hengbin'
'Schneider, Julia A.'
'Wei, Zitang'
'Lai, Wen-Yong'
'Huang, Wei'
'Wudl, Fred'
'Zheng, Yonghao'
_publ_section_title
;
 Catalyst-free one-step synthesis of ortho-tetraaryl perylene diimides for
 efficient OPV non-fullerene acceptors
;
_journal_issue                   11
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2781
_journal_paper_doi               10.1039/C7TC00263G
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C62 H62 N2 O4 S4'
_chemical_formula_weight         1027.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-13 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.575(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.251(3)
_cell_length_b                   20.123(8)
_cell_length_c                   21.102(9)
_cell_measurement_reflns_used    271
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      2
_cell_volume                     2649(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1294
_diffrn_reflns_av_unetI/netI     0.2147
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9982
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.586
_diffrn_reflns_theta_max         24.586
_diffrn_reflns_theta_min         1.400
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.5432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       needle
_exptl_crystal_F_000             1088
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.2448
_refine_ls_R_factor_gt           0.0935
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1240P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2069
_refine_ls_wR_factor_ref         0.2810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1699
_reflns_number_total             4356
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7tc00263g2.cif
_cod_data_source_block           z07082016_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7236705
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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
C1 C -0.1983(13) 0.3342(4) 0.2555(3) 0.048(2) Uani 1 1 d D . . A 4
C2 C -0.3080(14) 0.3905(4) 0.2564(3) 0.047(2) Uani 1 1 d D . . A 4
C4 C 0.0198(12) 0.4215(3) 0.3074(3) 0.0359(18) Uani 1 1 d . . . A 4
C5 C 0.1844(12) 0.4579(3) 0.3474(3) 0.0326(18) Uani 1 1 d . . . A 4
C6 C 0.3099(11) 0.5105(3) 0.3271(3) 0.0331(18) Uani 1 1 d . . . A 4
C7 C 0.3020(13) 0.5295(4) 0.2585(4) 0.047(2) Uani 1 1 d . . . A 4
C8 C 0.5301(12) 0.6258(4) 0.2853(3) 0.0372(18) Uani 1 1 d . . . A 4
C9 C 0.5755(11) 0.5999(3) 0.3511(3) 0.0309(17) Uani 1 1 d . . . A 4
C10 C 0.7216(11) 0.6306(3) 0.3939(3) 0.0309(17) Uani 1 1 d . . . A 4
C11 C 0.7435(11) 0.6065(3) 0.4562(3) 0.0350(18) Uani 1 1 d . . . A 4
H11 H 0.8465 0.6273 0.4848 0.042 Uiso 1 1 calc R U . A 4
C12 C 0.6262(11) 0.5550(3) 0.4788(3) 0.0323(17) Uani 1 1 d . . . A 4
C13 C 0.4770(11) 0.5221(3) 0.4355(3) 0.0314(17) Uani 1 1 d . . . A 4
C14 C 0.3526(11) 0.4688(3) 0.4550(3) 0.0315(17) Uani 1 1 d . . . A 4
C15 C 0.2092(12) 0.4379(3) 0.4116(3) 0.0351(18) Uani 1 1 d . . . A 4
H15 H 0.1249 0.4021 0.4255 0.042 Uiso 1 1 calc R U . A 4
C16 C 0.4533(11) 0.5443(3) 0.3707(3) 0.0313(17) Uani 1 1 d . . . A 4
C17 C 0.8644(12) 0.6863(3) 0.3797(3) 0.0396(19) Uani 1 1 d . . . A 4
C18 C 1.1611(15) 0.7541(5) 0.3502(5) 0.072(3) Uani 1 1 d D . . A 4
C19 C 1.0445(18) 0.7894(5) 0.3859(5) 0.075(3) Uani 1 1 d D . . A 4
C21 C 0.3806(15) 0.6118(4) 0.1746(3) 0.065(3) Uani 1 1 d . . . A 4
C22 C 0.2122(15) 0.6637(4) 0.1693(4) 0.067(3) Uani 1 1 d . . . A 4
H22A H 0.0793 0.6444 0.1846 0.080 Uiso 1 1 calc R U . A 4
H22B H 0.2566 0.7002 0.1987 0.080 Uiso 1 1 calc R U . A 4
C23 C 0.1589(14) 0.6932(4) 0.1064(3) 0.063(3) Uani 1 1 d . . . A 4
H23A H 0.1169 0.6570 0.0764 0.076 Uiso 1 1 calc R U . A 4
H23B H 0.2896 0.7142 0.0914 0.076 Uiso 1 1 calc R U . A 4
C24 C -0.0176(15) 0.7441(4) 0.1041(4) 0.070(3) Uani 1 1 d . . . A 4
H24A H -0.1477 0.7227 0.1191 0.084 Uiso 1 1 calc R U . A 4
H24B H 0.0244 0.7797 0.1348 0.084 Uiso 1 1 calc R U . A 4
C25 C -0.0767(15) 0.7760(5) 0.0421(4) 0.076(3) Uani 1 1 d . . . A 4
H25A H -0.1208 0.7407 0.0113 0.092 Uiso 1 1 calc R U . A 4
H25B H 0.0532 0.7973 0.0268 0.092 Uiso 1 1 calc R U . A 4
C26 C -0.2505(14) 0.8268(4) 0.0413(4) 0.071(3) Uani 1 1 d . . . A 4
H26A H -0.3834 0.8059 0.0535 0.107 Uiso 1 1 calc R U . A 4
H26B H -0.2726 0.8454 -0.0016 0.107 Uiso 1 1 calc R U . A 4
H26C H -0.2096 0.8624 0.0713 0.107 Uiso 1 1 calc R U . A 4
C28 C 0.663(2) 0.5352(7) 0.1361(5) 0.128(6) Uani 1 1 d . . . A 4
C29 C 0.708(3) 0.4980(8) 0.0866(6) 0.165(7) Uani 1 1 d . . . A 4
H29A H 0.7501 0.5294 0.0535 0.198 Uiso 1 1 calc R U . A 4
H29B H 0.5701 0.4781 0.0706 0.198 Uiso 1 1 calc R U . A 4
C30 C 0.870(3) 0.4421(8) 0.0874(6) 0.150(6) Uani 1 1 d . . . A 4
H30A H 0.9890 0.4585 0.1166 0.180 Uiso 1 1 calc R U . A 4
H30B H 0.8016 0.4062 0.1110 0.180 Uiso 1 1 calc R U . A 4
C31 C 0.969(4) 0.4101(8) 0.0433(8) 0.204(8) Uani 1 1 d . . . A 4
H31A H 0.9189 0.3640 0.0411 0.306 Uiso 1 1 calc R U . A 4
H31B H 1.1242 0.4107 0.0539 0.306 Uiso 1 1 calc R U . A 4
H31C H 0.9385 0.4317 0.0022 0.306 Uiso 1 1 calc R U . A 4
C3A C -0.1918(9) 0.4482(3) 0.2878(2) 0.0534(7) Uani 0.821(4) 1 d . . P A 4
C20A C 0.8565(8) 0.7559(2) 0.4107(2) 0.0670(9) Uani 0.701(5) 1 d . . P A 4
C3B C 0.0445(4) 0.33954(11) 0.29022(11) 0.0534(7) Uani 0.179(4) 1 d . . P A 4
C20B C 1.0673(5) 0.67954(14) 0.33533(14) 0.0670(9) Uani 0.299(5) 1 d . . P A 4
C27A C 0.463(3) 0.5724(11) 0.1257(8) 0.066(5) Uani 0.524(15) 1 d . . P A 4
N1 N 0.4121(10) 0.5868(3) 0.2422(3) 0.0405(16) Uani 1 1 d . . . A 4
O1 O 0.2089(10) 0.4967(3) 0.2179(2) 0.072(2) Uani 1 1 d . . . A 4
O2 O 0.5971(10) 0.6805(3) 0.2704(2) 0.0641(17) Uani 1 1 d . . . A 4
S1A S 0.0445(4) 0.33954(11) 0.29022(11) 0.0534(7) Uani 0.821(4) 1 d . . P A 4
S2A S 1.0673(5) 0.67954(14) 0.33533(14) 0.0670(9) Uani 0.701(5) 1 d . . P A 4
S1B S -0.1918(9) 0.4482(3) 0.2878(2) 0.0534(7) Uani 0.179(4) 1 d . . P A 4
S2B S 0.8565(8) 0.7559(2) 0.4107(2) 0.0670(9) Uani 0.299(5) 1 d . . P A 4
C27B C 0.581(4) 0.6117(12) 0.1427(9) 0.066(5) Uani 0.476(15) 1 d . . P A 4
H2 H -0.443(9) 0.401(2) 0.236(3) 0.07(3) Uiso 1 1 d D . . B 4
H18 H 1.275(9) 0.764(3) 0.324(3) 0.08(3) Uiso 1 1 d D . . C 4
H19 H 1.069(12) 0.830(4) 0.408(5) 0.19(6) Uiso 1 1 d D . . D 4
H1 H -0.239(9) 0.292(2) 0.239(4) 0.10(3) Uiso 1 1 d D . . E 4
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'
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'
H H 0.0000 0.0000 '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
C2 C1 C3B 113.7(6) .
C2 C1 H1 130(3) .
C3B C1 H1 116(3) .
C1 C2 C3A 115.5(7) .
C1 C2 H2 130(3) .
C3A C2 H2 114(3) .
C3A C4 C5 124.3(6) .
C3A C4 C3B 112.9(5) .
C5 C4 C3B 122.1(5) .
C6 C5 C15 118.6(6) .
C6 C5 C4 125.5(6) .
C15 C5 C4 115.9(6) .
C5 C6 C16 120.5(6) .
C5 C6 C7 120.2(7) .
C16 C6 C7 119.2(7) .
O1 C7 N1 120.0(7) .
O1 C7 C6 122.4(8) .
N1 C7 C6 117.5(7) .
O2 C8 N1 121.3(6) .
O2 C8 C9 120.2(7) .
N1 C8 C9 118.5(7) .
C10 C9 C16 120.1(6) .
C10 C9 C8 121.9(7) .
C16 C9 C8 117.9(6) .
C9 C10 C11 118.6(6) .
C9 C10 C17 126.1(6) .
C11 C10 C17 115.3(6) .
C12 C11 C10 124.4(7) .
C12 C11 H11 117.8 .
C10 C11 H11 117.8 .
C11 C12 C13 118.0(6) .
C11 C12 C14 123.8(6) 3_666
C13 C12 C14 118.2(6) 3_666
C14 C13 C12 121.3(6) .
C14 C13 C16 119.4(6) .
C12 C13 C16 119.3(6) .
C15 C14 C13 119.8(6) .
C15 C14 C12 119.7(7) 3_666
C13 C14 C12 120.5(6) 3_666
C14 C15 C5 122.2(7) .
C14 C15 H15 118.9 .
C5 C15 H15 118.9 .
C6 C16 C9 121.0(6) .
C6 C16 C13 119.5(6) .
C9 C16 C13 119.5(6) .
C10 C17 C20A 124.5(5) .
C10 C17 C20B 123.7(5) .
C20A C17 C20B 111.4(5) .
C19 C18 C20B 114.0(7) .
C19 C18 H18 134(3) .
C20B C18 H18 111(4) .
C18 C19 C20A 116.5(9) .
C18 C19 H19 133(3) .
C20A C19 H19 109(4) .
C27A C21 C27B 45.9(10) .
C27A C21 C22 128.6(9) .
C27B C21 C22 126.3(10) .
C27A C21 N1 117.9(9) .
C27B C21 N1 111.7(9) .
C22 C21 N1 110.8(6) .
C23 C22 C21 118.2(7) .
C23 C22 H22A 107.8 .
C21 C22 H22A 107.8 .
C23 C22 H22B 107.8 .
C21 C22 H22B 107.8 .
H22A C22 H22B 107.1 .
C22 C23 C24 115.4(7) .
C22 C23 H23A 108.4 .
C24 C23 H23A 108.4 .
C22 C23 H23B 108.4 .
C24 C23 H23B 108.4 .
H23A C23 H23B 107.5 .
C25 C24 C23 117.7(7) .
C25 C24 H24A 107.9 .
C23 C24 H24A 107.9 .
C25 C24 H24B 107.9 .
C23 C24 H24B 107.9 .
H24A C24 H24B 107.2 .
C24 C25 C26 116.6(8) .
C24 C25 H25A 108.1 .
C26 C25 H25A 108.1 .
C24 C25 H25B 108.1 .
C26 C25 H25B 108.1 .
H25A C25 H25B 107.3 .
C25 C26 H26A 109.5 .
C25 C26 H26B 109.5 .
H26A C26 H26B 109.5 .
C25 C26 H26C 109.5 .
H26A C26 H26C 109.5 .
H26B C26 H26C 109.5 .
C29 C28 C27A 113.0(15) .
C29 C28 C27B 133.0(12) .
C27A C28 C27B 42.3(9) .
C28 C29 C30 125.8(13) .
C28 C29 H29A 105.9 .
C30 C29 H29A 105.9 .
C28 C29 H29B 105.9 .
C30 C29 H29B 105.9 .
H29A C29 H29B 106.2 .
C31 C30 C29 134.4(16) .
C31 C30 H30A 103.6 .
C29 C30 H30A 103.6 .
C31 C30 H30B 103.6 .
C29 C30 H30B 103.6 .
H30A C30 H30B 105.3 .
C30 C31 H31A 109.5 .
C30 C31 H31B 109.5 .
H31A C31 H31B 109.5 .
C30 C31 H31C 109.5 .
H31A C31 H31C 109.5 .
H31B C31 H31C 109.5 .
C4 C3A C2 104.2(5) .
C19 C20A C17 102.4(6) .
C1 C3B C4 93.7(4) .
C17 C20B C18 95.5(5) .
C21 C27A C28 121.4(14) .
C8 N1 C7 123.9(6) .
C8 N1 C21 117.7(7) .
C7 N1 C21 118.0(7) .
C21 C27B C28 108.8(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.325(10) .
C1 C3B 1.647(8) .
C1 H1 0.94(4) .
C2 C3A 1.501(9) .
C2 H2 0.94(4) .
C4 C3A 1.462(8) .
C4 C5 1.483(9) .
C4 C3B 1.698(7) .
C5 C6 1.400(9) .
C5 C15 1.413(9) .
C6 C16 1.418(9) .
C6 C7 1.494(9) .
C7 O1 1.203(8) .
C7 N1 1.398(9) .
C8 O2 1.226(8) .
C8 N1 1.379(9) .
C8 C9 1.494(9) .
C9 C10 1.388(9) .
C9 C16 1.431(9) .
C10 C11 1.402(9) .
C10 C17 1.475(9) .
C11 C12 1.372(9) .
C11 H11 0.9500 .
C12 C13 1.428(9) .
C12 C14 1.474(9) 3_666
C13 C14 1.402(9) .
C13 C16 1.437(9) .
C14 C15 1.388(9) .
C14 C12 1.474(9) 3_666
C15 H15 0.9500 .
C17 C20A 1.548(8) .
C17 C20B 1.629(7) .
C18 C19 1.294(13) .
C18 C20B 1.634(11) .
C18 H18 0.94(4) .
C19 C20A 1.478(11) .
C19 H19 0.95(4) .
C21 C27A 1.42(2) .
C21 C27B 1.46(2) .
C21 C22 1.482(10) .
C21 N1 1.513(9) .
C22 C23 1.473(10) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.505(10) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.483(10) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C26 1.490(11) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C28 C29 1.329(16) .
C28 C27A 1.46(2) .
C28 C27B 1.63(2) .
C29 C30 1.514(18) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C30 C31 1.317(18) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
