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_1559376
_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             2019-11-02
_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                65.789(14)
_cell_angle_beta                 65.996(13)
_cell_angle_gamma                72.836(14)
_cell_formula_units_Z            2
_cell_length_a                   14.699(2)
_cell_length_b                   17.173(3)
_cell_length_c                   17.727(2)
_cell_measurement_reflns_used    1524
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      45.5520
_cell_measurement_theta_min      2.9060
_cell_volume                     3683.8(10)
_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 0.967
_diffrn_measured_fraction_theta_max 0.927
_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    -85.00  12.00   0.50    5.00    --    0.00 -37.00 -90.00  194
  2  \w    -86.00 -50.00   0.50    5.00    --    0.00 -19.00 -30.00   72
  3  \w    -45.00  13.00   0.50    5.00    --    0.00 -72.00-180.00  116
  4  \w    -69.00  -1.00   0.50    5.00    --    0.00 -72.00  90.00  136
  5  \w    -83.00 -28.00   0.50   20.00    --    5.00 -57.00 150.00  110
  6  \w     -7.00  43.00   0.50   20.00    --    5.00  19.00 -60.00  100
  7  \w     -7.00  18.00   0.50   20.00    --    5.00 -57.00 150.00   50
  8  \w   -111.00  -9.00   0.50   20.00    --  -98.80  19.00-180.00  204
  9  \w    -94.00 -62.00   0.50   20.00    --  -98.80  72.00  30.00   64
 10  \w    -53.00 -27.00   0.50   20.00    --  -98.80  72.00 120.00   52
 11  \w    -98.00 -68.00   0.50   20.00    --  -98.80  72.00  90.00   60
 12  \w   -113.00  -9.00   0.50   20.00    --  -98.80  57.00-150.00  208
 13  \w    -96.00 -47.00   0.50   20.00    --  -98.80  72.00 -30.00   98
 14  \w    -88.00 -62.00   0.50   20.00    --  -98.80  72.00 -90.00   52
 15  \w    -92.00 -34.00   0.50   20.00    --  -98.80  72.00-150.00  116
 16  \w   -106.00 -42.00   0.50   20.00    --  -98.80  72.00   0.00  128
 17  \w    -94.00  -9.00   0.50   20.00    --  -98.80  57.00 -60.00  170
 18  \w   -110.00 -16.00   0.50   20.00    --  -98.80  19.00  90.00  188
 19  \w   -111.00 -25.00   0.50   20.00    --  -98.80  72.00-120.00  172
 20  \w   -111.00 -70.00   0.50   20.00    --  -98.80  72.00-180.00   82
 21  \w   -111.00 -24.00   0.50   20.00    --  -98.80  72.00  60.00  174
 22  \w   -110.00 -83.00   0.50   20.00    --  -98.80  72.00 150.00   54
 23  \w   -113.00 -21.00   0.50   20.00    --  -98.80  72.00 -60.00  184
 24  \w   -111.00 -57.00   0.50   20.00    --  -98.80  72.00 120.00  108
 25  \w   -184.00 -66.00   0.50   20.00    --  -98.80   0.00 150.00  236
;
_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      0.0225021000
_diffrn_orient_matrix_UB_12      0.0874458000
_diffrn_orient_matrix_UB_13      -0.0721124000
_diffrn_orient_matrix_UB_21      -0.1012066000
_diffrn_orient_matrix_UB_22      0.0134610000
_diffrn_orient_matrix_UB_23      -0.0138079000
_diffrn_orient_matrix_UB_31      -0.0522788000
_diffrn_orient_matrix_UB_32      0.0456215000
_diffrn_orient_matrix_UB_33      0.0691608000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1741
_diffrn_reflns_av_unetI/netI     0.2686
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37726
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.913
_diffrn_reflns_theta_min         2.855
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81882
_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    1.306
_exptl_crystal_description       needle
_exptl_crystal_F_000             1532
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     898
_refine_ls_number_reflns         13864
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.3262
_refine_ls_R_factor_gt           0.1302
_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^)+(0.1878P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3220
_refine_ls_wR_factor_ref         0.4378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3722
_reflns_number_total             13864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ee02251a2.cif
_cod_data_source_block           ly_dcl_1
_cod_depositor_comments
'Adding full bibliography for 1559374--1559377.cif.'
_cod_original_cell_volume        3683.8(11)
_cod_database_code               1559376
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 97.13
_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(C02M) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C02G) \\sim Ueq, Uanis(C02P) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C01Z)
\\sim Ueq, Uanis(C02C) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C01Z(H01Z), C02B(H02V)
3.b Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B), C00P(H00C,H00D), C01A(H01A,H01B), C01M(H01C,H01D), C01R(H01E,
 H01F), C01S(H01G,H01H), C01T(H01L,H01M), C01U(H01O,H01P), C01W(H01Q,H01R),
 C01X(H01S,H01T), C020(H02A,H02B), C023(H02F,H02G), C024(H02H,H02I), C025(H02J,
 H02K), C026(H02L,H02M), C027(H02N,H02O), C028(H02P,H02Q), C029(H02R,H02S),
 C02A(H02T,H02U), C02C(H02W,H02X), C02D(H02Y,H), C02F(H02,HC), C02G(H0AA,HD),
 C02J(H3AA,HI), C02K(H4AA,HJ), C02L(H5AA,HK), C02M(H6AA,HL), C02N(H7AA,HM),
 C02P(H9AA,HP), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C013(H013), C018(H018), C01I(H01I), C01J(H01J), C01K(H01K),
 C01N(H01N), C021(H021)
3.d Idealised Me refined as rotating group:
 C01Y(H01U,H01V,H01W), C022(H02C,H02D,H02E), C02E(H02Z,HA,HB), C02H(H1AA,HE,
 HF), C02I(H2AA,HG,HH), C02O(H8AA,HN,HO)
;
_shelx_res_checksum              58727
_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 2.044
_oxdiff_exptl_absorpt_empirical_full_min 0.597