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_1559374
_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         'C68 H68 Cl2 N4 O4 S2'
_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             2018-11-16
_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                88.307(2)
_cell_angle_beta                 76.712(2)
_cell_angle_gamma                82.866(2)
_cell_formula_units_Z            2
_cell_length_a                   13.3351(4)
_cell_length_b                   16.6987(4)
_cell_length_c                   17.3392(3)
_cell_measurement_reflns_used    14660
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.2370
_cell_measurement_theta_min      4.0550
_cell_volume                     3728.61(16)
_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 0.979
_diffrn_measured_fraction_theta_max 0.979
_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    -36.00  12.00   0.50    0.85    --    0.00 -57.00  90.00   96
  2  \w    -47.00  12.00   0.50    0.85    --    0.00 -57.00 -60.00  118
  3  \w    -74.00   7.00   0.50    0.85    --    0.00 -72.00-120.00  162
  4  \w     26.00  87.00   0.50    0.85    --    0.00  38.00 120.00  122
  5  \w    -87.00 -60.00   0.50    0.85    --    0.00 -57.00  90.00   54
  6  \w     -3.00  24.00   0.50    0.85    --    0.00  38.00 120.00   54
  7  \w    -78.00 -46.00   0.50    0.85    --    0.00 -19.00-180.00   64
  8  \w    -36.00  11.00   0.50    0.85    --    0.00 -19.00 -60.00   94
  9  \w   -113.00 -58.00   0.50    3.41    --  -98.80  72.00  90.00  110
 10  \w   -105.00 -71.00   0.50    3.41    --  -98.80  72.00 150.00   68
 11  \w   -112.00 -16.00   0.50    3.41    --  -98.80  72.00-120.00  192
 12  \w   -113.00 -31.00   0.50    3.41    --  -98.80  72.00  60.00  164
 13  \w    -48.00 -22.00   0.50    3.41    --  -98.80  72.00   0.00   52
 14  \w   -102.00  -9.00   0.50    3.41    --  -98.80  19.00 150.00  186
 15  \w    -48.00 -13.00   0.50    3.41    --  -98.80  57.00-120.00   70
 16  \w    -66.00 -14.00   0.50    3.41    --  -98.80  72.00-180.00  104
 17  \w   -113.00 -43.00   0.50    3.41    --  -98.80  72.00  30.00  140
 18  \w   -112.00  -9.00   0.50    3.41    --  -98.80  19.00  60.00  206
 19  \w   -112.00 -49.00   0.50    3.41    --  -98.80  72.00 -30.00  126
 20  \w   -112.00 -73.00   0.50    3.41    --  -98.80  72.00 120.00   78
 21  \w   -114.00 -85.00   0.50    3.41    --  -98.80 -19.00-120.00   58
 22  \w   -112.00 -57.00   0.50    3.41    --  -98.80  72.00-150.00  110
 23  \w   -106.00 -10.00   0.50    3.41    --  -98.80  57.00-180.00  192
 24  \w    -95.00 -46.00   0.50    3.41    --  -98.80  72.00 -90.00   98
 25  \w   -103.00 -76.00   0.50    3.41    --  -98.80  72.00-180.00   54
 26  \w   -103.00 -61.00   0.50    3.41    --  -98.80  72.00   0.00   84
 27  \w   -183.00 -14.00   0.50    3.41    --  -98.80   0.00  30.00  338
;
_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      -0.0409806000
_diffrn_orient_matrix_UB_12      0.0622132000
_diffrn_orient_matrix_UB_13      0.0671986000
_diffrn_orient_matrix_UB_21      0.1007552000
_diffrn_orient_matrix_UB_22      0.0398274000
_diffrn_orient_matrix_UB_23      -0.0251992000
_diffrn_orient_matrix_UB_31      -0.0496811000
_diffrn_orient_matrix_UB_32      0.0564616000
_diffrn_orient_matrix_UB_33      -0.0564249000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36794
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         2.618
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    1.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68028
_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            'dull dark brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.016
_exptl_crystal_description       plate
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     727
_refine_ls_number_reflns         13037
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0889
_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^)+(0.1482P)^2^+8.1199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2740
_refine_ls_wR_factor_ref         0.2882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9812
_reflns_number_total             13037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ee02251a2.cif
_cod_data_source_block           mo_cl_1
_cod_depositor_comments
'Adding full bibliography for 1559374--1559377.cif.'
_cod_database_code               1559374
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.923
_reflns_odcompleteness_completeness 98.20
_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. Uiso/Uaniso restraints and constraints
Uanis(N02G) \\sim Ueq, Uanis(N026) \\sim Ueq, Uanis(N029) \\sim Ueq,
Uanis(N022) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C02F) \\sim Ueq, Uanis(C02C) \\sim Ueq, Uanis(C02E) \\sim Ueq,
Uanis(C02D) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C00V(H00C,H00D), C00Y(H00E,H00F), C012(H01A,H01B), C015(H01C,
 H01D), C016(H01E,H01F), C017(H01G,H01H), C01B(H01I,H01J), C01F(H01L,H01M),
 C01H(H01Q,H01R), C01I(H01S,H01T), C01O(H01W,H01X), C01P(H01Y,H), C01U(H0AA,HC),
  C01V(H1AA,HD), C01X(H3AA,HE), C01Y(H4AA,HF), C01Z(H5AA,HG), C023(H02A,H02B),
 C025(H02C,H02D)
3.b Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C00T(H00T), C010(H010), C011(H011), C019(H019), C01D(H01K),
 C01J(H01U), C01N(H01V), C01R(H01Z), C01W(H2AA)
3.c Idealised Me refined as rotating group:
 C01G(H01N,H01O,H01P), C01S(H01,HA,HB), C027(H02E,H02F,H02G), C028(H02H,H02I,
 H02J), C02A(H02K,H02L,H02M), C02B(H02N,H02O,H02P)
;
_shelx_res_checksum              80894
_shelx_fab_checksum              81032
_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 1.813
_oxdiff_exptl_absorpt_empirical_full_min 0.496