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_1559375
_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         'C82 H88 Cl2 N8 O2 S5'
_chemical_formula_sum            'C82 H88 Cl2 N8 O2 S5'
_chemical_formula_weight         1448.80
_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             2019-11-18
_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                105.241(3)
_cell_angle_beta                 94.313(4)
_cell_angle_gamma                99.330(3)
_cell_formula_units_Z            2
_cell_length_a                   13.6375(6)
_cell_length_b                   15.3980(5)
_cell_length_c                   19.4824(6)
_cell_measurement_reflns_used    4123
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      51.3560
_cell_measurement_theta_min      3.2960
_cell_volume                     3865.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.937
_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    -88.00 -61.00   0.50    6.00    --    0.00 -37.00 -60.00   54
  2  \w    -40.00 -14.00   0.50    6.00    --    0.00 -19.00  30.00   52
  3  \w      1.00  77.00   0.50    6.00    --    0.00  19.00-120.00  152
  4  \w    -81.00  13.00   0.50    6.00    --    0.00 -72.00 120.00  188
  5  \w    -56.00  12.00   0.50    6.00    --    0.00 -37.00 -60.00  136
  6  \w    -88.00   8.00   0.50    6.00    --    0.00 -57.00 -90.00  192
  7  \w   -105.00 -67.00   0.50   24.00    --  -98.80  72.00 -30.00   76
  8  \w   -100.00 -29.00   0.50   24.00    --  -98.80  72.00 150.00  142
  9  \w   -112.00 -27.00   0.50   24.00    --  -98.80  72.00-120.00  170
 10  \w   -113.00 -65.00   0.50   24.00    --  -98.80  72.00 120.00   96
 11  \w   -113.00 -35.00   0.50   24.00    --  -98.80  72.00 -60.00  156
 12  \w   -110.00 -26.00   0.50   24.00    --  -98.80  72.00-180.00  168
 13  \w   -101.00  -9.00   0.50   24.00    --  -98.80  57.00  60.00  184
 14  \w    -82.00 -57.00   0.50   24.00    --  -98.80  57.00-120.00   50
 15  \w   -112.00 -10.00   0.50   24.00    --  -98.80  19.00  30.00  204
 16  \w    -90.00 -10.00   0.50   24.00    --  -98.80  57.00 150.00  160
 17  \w   -113.00 -60.00   0.50   24.00    --  -98.80  72.00  30.00  106
 18  \w   -111.00 -14.00   0.50   24.00    --  -98.80  19.00 -60.00  194
 19  \w   -112.00 -26.00   0.50   24.00    --  -98.80  72.00  60.00  172
 20  \w    -92.00 -64.00   0.50   24.00    --  -98.80  72.00 -90.00   56
 21  \w   -113.00 -63.00   0.50   24.00    --  -98.80  72.00   0.00  100
 22  \w   -120.00 -10.00   0.50   24.00    --  -98.80   0.00 -90.00  220
 23  \w   -187.00-132.00   0.50   24.00    --  -98.80 -19.00 -60.00  110
 24  \w   -188.00-173.00   0.50   24.00    --  -98.80   0.00 -90.00   30
;
_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      -0.0381955000
_diffrn_orient_matrix_UB_12      0.0798326000
_diffrn_orient_matrix_UB_13      -0.0203851000
_diffrn_orient_matrix_UB_21      0.0008632000
_diffrn_orient_matrix_UB_22      -0.0481961000
_diffrn_orient_matrix_UB_23      -0.0799205000
_diffrn_orient_matrix_UB_31      -0.1088565000
_diffrn_orient_matrix_UB_32      -0.0495526000
_diffrn_orient_matrix_UB_33      -0.0043129000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.1197
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40074
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.935
_diffrn_reflns_theta_min         3.029
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.419
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.245
_exptl_crystal_description       needle
_exptl_crystal_F_000             1532
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.193
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     898
_refine_ls_number_reflns         14686
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1814
_refine_ls_R_factor_gt           0.0961
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1799P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2539
_refine_ls_wR_factor_ref         0.3134
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6867
_reflns_number_total             14686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ee02251a2.cif
_cod_data_source_block           ly_dcl_2
_cod_depositor_comments
'Adding full bibliography for 1559374--1559377.cif.'
_cod_database_code               1559375
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.09
_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
 C22-C24
 2.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C22) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C2AA) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C24) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C02C) \\sim Ueq, Uanis(C02E) \\sim Ueq, Uanis(C02G) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C027) \\sim Ueq, Uanis(C025) \\sim Ueq, Uanis(C024) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C25) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C0AA) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C027(H027), C22(H22)
4.b Secondary CH2 refined with riding coordinates:
 C01A(H01A,H01B), C01G(H01C,H01D), C01I(H01E,H01F), C01L(H01G,H01H), C01N(H01I,
 H01J), C01P(H01K,H01L), C01R(H01N,H01P), C01V(H01R,H01S), C01W(H01T,H01U),
 C01X(H01V,H01W), C01Y(H01X,H01Y), C01Z(H01Z,H), C020(H02A,H02B), C022(H02C,
 H02D), C025(H02H,H02I), C026(H02J,H02K), C028(H02L,H02M), C02B(H02Q,H02R),
 C02C(H02S,H02T), C02D(H02U,H02V), C02E(H02W,H02X), C12(H12A,H12B), C15(H15A,
 H15B), C21(H21A,H21B), C16(H16A,H16B), C25(H25A,H25B), C33(H33A,H33B), C5(H5A,
 H5B), C3(H3A,H3B), C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C015(H015), C016(H016), C018(H018), C019(H019), C01M(H01M),
 C01O(H01O), C01Q(H01Q)
4.d Idealised Me refined as rotating group:
 C024(H02E,H02F,H02G), C02A(H02N,H02O,H02P), C02G(H02Y,HA,HB), C24(H24A,H24B,
 H24C), C2AA(H2AA,H2AB,H2AC), C0AA(H0AA,H0AB,H0AC)
;
_shelx_res_checksum              38430
_shelx_fab_checksum              85421
_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 1.566
_oxdiff_exptl_absorpt_empirical_full_min 0.544