Effect of the chlorine substitution position of the end-group on intermolecular interactions and photovoltaic performance of small molecule acceptors
Li, Xiaojun; Angunawela, Indunil; Chang, Yuan; Zhou, Jiadong; Huang, He; Zhong, Lian; Liebman-Pelaez, Alex; Zhu, Chenhui; Meng, Lei; Xie, Zengqi; Ade, Harald; Yan, He; Li, Yongfang; Energy & Environmental Science 13 (2020) 5028–5038; doi:10.1039/D0EE02251A

data_1559377
_publ_section_title
;
 Effect of the chlorine substitution position of the end-group on
 intermolecular interactions and photovoltaic performance of small
 molecule acceptors
;
_journal_issue                   12
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              5028
_journal_page_last               5038
_journal_paper_doi               10.1039/D0EE02251A
_journal_volume                  13
_journal_year                    2020
_chemical_formula_moiety         '2(C34 H34 Cl N2 O2 S)'
_chemical_formula_sum            'C68 H68 Cl2 N4 O4 S2'
_chemical_formula_weight         1140.28
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-16 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                106.356(7)
_cell_angle_beta                 113.691(7)
_cell_angle_gamma                95.799(8)
_cell_formula_units_Z            2
_cell_length_a                   14.6444(12)
_cell_length_b                   15.9434(16)
_cell_length_c                   17.9860(11)
_cell_measurement_reflns_used    6013
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      70.6600
_cell_measurement_theta_min      3.0150
_cell_volume                     3578.6(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -87.00 -49.00   0.50    3.93    --    0.00 -57.00-150.00   76
  2  \w    -30.00  10.00   0.50    3.93    --    0.00 -72.00 -60.00   80
  3  \w     -7.00  20.00   0.50    3.93    --    0.00  72.00 -90.00   54
  4  \w    -88.00  12.00   0.50    3.93    --    0.00 -57.00 120.00  200
  5  \w    -40.00  13.00   0.50    3.93    --    0.00 -57.00-150.00  106
  6  \w    -80.00 -40.00   0.50    3.93    --    0.00 -72.00 -60.00   80
  7  \w    -87.00 -34.00   0.50    3.93    --    0.00 -19.00   0.00  106
  8  \w      4.00  31.00   0.50    3.93    --    0.00  19.00  90.00   54
  9  \w   -102.00 -31.00   0.50   15.73    --  -98.80  72.00-150.00  142
 10  \w    -97.00 -70.00   0.50   15.73    --  -98.80  72.00-120.00   54
 11  \w   -112.00 -43.00   0.50   15.73    --  -98.80  72.00  90.00  138
 12  \w   -112.00 -41.00   0.50   15.73    --  -98.80  72.00  60.00  142
 13  \w    -94.00 -55.00   0.50   15.73    --  -98.80  72.00 -60.00   78
 14  \w   -112.00 -11.00   0.50   15.73    --  -98.80  48.00-138.00  202
 15  \w   -100.00 -22.00   0.50   15.73    --  -98.80  72.00 -90.00  156
 16  \w   -112.00 -22.00   0.50   15.73    --  -98.80  19.00  60.00  180
 17  \w    -89.00 -62.00   0.50   15.73    --  -98.80  72.00  30.00   54
 18  \w    -55.00 -13.00   0.50   15.73    --  -98.80  57.00 120.00   84
 19  \w    -85.00 -45.00   0.50   15.73    --  -98.80  72.00 -30.00   80
 20  \w   -113.00 -73.00   0.50   15.73    --  -98.80  72.00-180.00   80
 21  \w    -79.00 -10.00   0.50   15.73    --  -98.80  57.00 -90.00  138
 22  \w   -110.00 -35.00   0.50   15.73    --  -98.80  72.00   0.00  150
 23  \w   -106.00 -13.00   0.50   15.73    --  -98.80  19.00 150.00  186
 24  \w    -49.00 -23.00   0.50   15.73    --  -98.80  72.00 -60.00   52
 25  \w   -185.00 -15.00   0.50   15.73    --  -98.80   0.00 150.00  340
 26  \w   -104.00 -45.00   0.50   15.73    --  -98.80  72.00 136.09  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0046351000
_diffrn_orient_matrix_UB_12      0.0669093000
_diffrn_orient_matrix_UB_13      -0.0479800000
_diffrn_orient_matrix_UB_21      0.1173913000
_diffrn_orient_matrix_UB_22      0.0182223000
_diffrn_orient_matrix_UB_23      0.0331132000
_diffrn_orient_matrix_UB_31      -0.0151277000
_diffrn_orient_matrix_UB_32      -0.0772826000
_diffrn_orient_matrix_UB_33      -0.0812474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31592
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         2.868
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    1.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_description       needle
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.619
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     722
_refine_ls_number_reflns         12454
_refine_ls_number_restraints     174
_refine_ls_restrained_S_all      1.289
_refine_ls_R_factor_all          0.2605
_refine_ls_R_factor_gt           0.2023
_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/[\s^2^(Fo^2^)+(0.3500P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5001
_refine_ls_wR_factor_ref         0.5666
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6206
_reflns_number_total             12454
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ee02251a2.cif
_cod_data_source_block           mo_cl_2
_cod_depositor_comments
'Adding full bibliography for 1559374--1559377.cif.'
_cod_database_code               1559377
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.822
_reflns_odcompleteness_completeness 97.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C01F-C01G = C01G-C01P = C01P-C01T = C01T-C14 = C14-C021
 1.54 with sigma of 0.01
 C01D-C01L = C01L-C01U = C01U-C01X = C01X-C020 = C020-C022
 1.54 with sigma of 0.01
 C014-C01I = C01I-C01S = C01S-C15 = C15-C7 = C7-C1AA
 1.54 with sigma of 0.01
 C01B-C01H = C01H-C01W = C01W-C01Z = C01Z-C0AA = C0AA-C11
 1.54 with sigma of 0.01
 C01Z-C11
 2.45 with sigma of 0.01
3. Rigid bond restraints
 C01B, C01H, C01W, C01Z, C0AA, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C01F) \\sim Ueq, Uanis(C01G) \\sim Ueq, Uanis(C01P) \\sim Ueq,
Uanis(C01T) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C021) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C01D) \\sim Ueq, Uanis(C01L) \\sim Ueq, Uanis(C01U) \\sim Ueq,
Uanis(C01X) \\sim Ueq, Uanis(C020) \\sim Ueq, Uanis(C022) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C014) \\sim Ueq, Uanis(C01I) \\sim Ueq, Uanis(C01S) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C1AA) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C01B) \\sim Ueq, Uanis(C01H) \\sim Ueq, Uanis(C01W) \\sim Ueq,
Uanis(C01Z) \\sim Ueq, Uanis(C0AA) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C014(H01Q,H01R), C01B(H01T,H01U), C01D(H01A,H01B), C01F(H01C,H01D), C01G(H01E,
 H01F), C01H(H01V,H01W), C01I(H01X,H01Y), C01L(H01G,H01H), C01P(H01I,H01J),
 C01S(H01,H), C01T(H01K,H01L), C01U(H01M,H01N), C01W(H0AA,HA), C01X(H01O,H01P),
 C01Z(H1AA,HB), C020(H02A,H02B), C14(H14A,H14B), C15(H15A,H15B), C0AA(H0AB,
 H0AC), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00J(H00J), C00T(H00T), C00Z(H00Z), C010(H010), C013(H013),
 C015(H015), C019(H019), C01A(H01S), C01K(H01Z)
5.c Idealised Me refined as rotating group:
 C00X(H00B,H00C,H00D), C021(H02C,H02D,H02E), C022(H02F,H02G,H02H), C5(H5A,H5B,
 H5C), C11(H11A,H11B,H11C), C1AA(H1AB,H1AC,H1AD)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.704
_oxdiff_exptl_absorpt_empirical_full_min 0.401