Meta-analysis: the molecular organization of non-fullerene acceptors
Mondelli, Pierluigi; Boschetto, Gabriele; Horton, Peter N.; Tiwana, Priti; Skylaris, Chris-Kriton; Coles, Simon J.; Krompiec, Michal; Morse, Graham; Materials Horizons 7 (2020) 1062–1072; doi:10.1039/C9MH01439J

data_1552934
_publ_section_title
;
 Meta-analysis: the molecular organization of non-fullerene acceptors
;
_journal_issue                   4
_journal_name_full               'Materials Horizons'
_journal_page_first              1062
_journal_page_last               1072
_journal_paper_doi               10.1039/C9MH01439J
_journal_volume                  7
_journal_year                    2020
_chemical_formula_moiety         '2(C47 H41 N2 O S2), C H Cl3'
_chemical_formula_sum            'C95 H83 Cl3 N4 O2 S4'
_chemical_formula_weight         1547.24
_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             2019-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-24 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                87.770(8)
_cell_angle_beta                 88.724(9)
_cell_angle_gamma                78.001(12)
_cell_formula_units_Z            2
_cell_length_a                   8.7454(13)
_cell_length_b                   18.872(2)
_cell_length_c                   25.2647(18)
_cell_measurement_reflns_used    2866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2090
_cell_measurement_theta_min      2.4540
_cell_volume                     4075.1(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -89.00  48.00   0.50   20.00    --    0.00  28.00  58.00  274
  2  \w    -88.00  88.00   0.50   20.00    --    0.00  10.00-150.00  352
  3  \w    -84.00  94.00   0.50   20.00    --    5.00  28.00  58.00  356
  4  \w   -179.00  -1.00   0.50  100.00    --  -90.00  28.00  58.00  356
  5  \w   -178.00-120.00   0.50  100.00    --  -90.00  59.00 171.21  116
  6  \w   -178.00-119.00   0.50  100.00    --  -90.00  59.00   5.82  118
  7  \w   -111.00 -84.00   0.50  100.00    --  -90.00  59.00   5.82   54
  8  \w    -53.00 -22.00   0.50  100.00    --  -90.00  59.00   5.82   62
  9  \w   -178.00-153.00   0.50  100.00    --  -90.00  58.00-134.21   50
 10  \w   -101.00 -74.00   0.50  100.00    --  -90.00  58.00  60.95   54
 11  \w   -135.00 -12.00   0.50  100.00    --  -90.00  58.00-134.21  246
 12  \w   -178.00-151.00   0.50  100.00    --  -90.00  59.00 -53.70   54
 13  \w   -148.00 -96.00   0.50  100.00    --  -90.00  59.00 -53.70  104
 14  \w    -87.00  -2.00   0.50  100.00    --  -90.00  59.00 -53.70  170
 15  \w   -179.00  -5.00   0.50  100.00    --  -90.00  59.00 108.53  348
 16  \w   -179.00-141.00   0.50  100.00    --  -90.00  58.00  60.95   76
 17  \w   -113.00  -2.00   0.50  100.00    --  -90.00  59.00 171.21  222
 18  \w   -177.00-102.00   0.50  100.00    --  -90.00   0.00 -30.00  150
 19  \w    -89.00 -39.00   0.50  100.00    --  -90.00   0.00 -30.00  100
 20  \w    -33.00  -2.00   0.50  100.00    --  -90.00   0.00 -30.00   62
 21  \w   -172.00-141.00   0.50  100.00    --  -90.00  59.00-113.29   62
 22  \w   -178.00-119.00   0.50  100.00    --  -90.00  49.00 120.00  118
 23  \w   -179.00 -23.00   0.50  100.00    --  -90.00  57.00 -87.97  312
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter \c goniometer'
_diffrn_measurement_device_type
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0225117000
_diffrn_orient_matrix_UB_12      -0.0709938000
_diffrn_orient_matrix_UB_13      -0.0238099000
_diffrn_orient_matrix_UB_21      0.1681615000
_diffrn_orient_matrix_UB_22      -0.0367293000
_diffrn_orient_matrix_UB_23      0.0153029000
_diffrn_orient_matrix_UB_31      -0.0604563000
_diffrn_orient_matrix_UB_32      -0.0241722000
_diffrn_orient_matrix_UB_33      0.0540694000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.1316
_diffrn_reflns_av_unetI/netI     0.1258
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            43879
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        58.930
_diffrn_reflns_theta_max         58.930
_diffrn_reflns_theta_min         2.395
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    2.380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       needle
_exptl_crystal_F_000             1624
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of Pet. ether and chloroform'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.146
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.450
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1028
_refine_ls_number_reflns         11657
_refine_ls_number_restraints     1813
_refine_ls_restrained_S_all      1.408
_refine_ls_R_factor_all          0.3079
_refine_ls_R_factor_gt           0.1768
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4418
_refine_ls_wR_factor_ref         0.5171
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4311
_reflns_number_total             11657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9mh01439j2.cif
_cod_data_source_block           m-ITIC
_cod_depositor_comments
;Adding full bibliography for 1552926--1552934.cif.

 Adding full bibliography for 1552926--1552934.cif.
;
_cod_original_cell_volume        4075.1(9)
_cod_database_code               1552934
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C94H82N4O2S4
_chemical_oxdiff_usercomment     'Sample #21: m-ITIC'
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.717
_reflns_odcompleteness_completeness 98.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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
 C42-C43 = C80-C81 = C30-C31 = C92-C93
 1.54 with sigma of 0.02
 C93-C94 \\sim C93A-C94A
 with sigma of 0.02
 C94-C95 \\sim C94A-C95A
 with sigma of 0.02
 C95-C96 \\sim C95A-C96A
 with sigma of 0.02
 C93-C95 \\sim C93A-C95A
 with sigma of 0.04
 C94-C96 \\sim C94A-C96A
 with sigma of 0.04
 C30-C26 \\sim C80-C76 \\sim C42-C38 \\sim C92-C88
 with sigma of 0.02
 C92-C93 \\sim C92A-C93A
 with sigma of 0.02
 C88-C93 \\sim C90-C93A
 with sigma of 0.04
 C92-C94 \\sim C92A-C94A
 with sigma of 0.04
 C92A-C90 \\sim C92-C88
 with sigma of 0.02
 C47-C46 \\sim C46-C45 \\sim C45-C44 \\sim C44-C43 \\sim C43-C42
 with sigma of 0.02
 C47-C45 \\sim C45-C43 \\sim C46-C44 \\sim C44-C42
 with sigma of 0.04
 C35-C34 \\sim C34-C33 \\sim C33-C32 \\sim C32-C31 \\sim C31-C30
 with sigma of 0.02
 C35-C33 \\sim C33-C31 \\sim C34-C32 \\sim C32-C30
 with sigma of 0.04
 C80-C81 \\sim C81-C82 \\sim C82-C83 \\sim C83-C84 \\sim C84-C85
 with sigma of 0.02
 C80-C82 \\sim C82-C84 \\sim C81-C83 \\sim C83-C85
 with sigma of 0.04
 C96-C97 \\sim C96A-C97A
 with sigma of 0.02
 C95-C97 \\sim C95A-C97A
 with sigma of 0.04
 C97-C96 \\sim C96-C95 \\sim C95-C94 \\sim C94-C93 \\sim C93-C92
 with sigma of 0.02
 C97-C95 \\sim C95-C93 \\sim C96-C94 \\sim C94-C92
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H88)=Sof(C92A)=Sof(H92C)=Sof(H92D)=Sof(C93A)=Sof(H93C)=Sof(H93D)=
 Sof(C94A)=Sof(H94C)=Sof(H94D)=Sof(C95A)=Sof(H95C)=Sof(H95D)=Sof(C96A)=
 Sof(H96C)=Sof(H96D)=Sof(C97A)=Sof(H97D)=Sof(H97E)=Sof(H97F)=1-FVAR(1)
 Sof(H90)=Sof(C92)=Sof(H92A)=Sof(H92B)=Sof(C93)=Sof(H93A)=Sof(H93B)=Sof(C94)=
 Sof(H94A)=Sof(H94B)=Sof(C95)=Sof(H95A)=Sof(H95B)=Sof(C96)=Sof(H96A)=Sof(H96B)=
 Sof(C97)=Sof(H97A)=Sof(H97B)=Sof(H97C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C101(H101)
6.b Secondary CH2 refined with riding coordinates:
 C80(H80A,H80B), C81(H81A,H81B), C82(H82A,H82B), C83(H83A,H83B), C84(H84A,
 H84B), C92(H92A,H92B), C93(H93A,H93B), C94(H94A,H94B), C95(H95A,H95B),
 C96(H96A,H96B), C92A(H92C,H92D), C93A(H93C,H93D), C94A(H94C,H94D), C95A(H95C,
 H95D), C96A(H96C,H96D), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B),
 C33(H33A,H33B), C34(H34A,H34B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B),
  C45(H45A,H45B), C46(H46A,H46B)
6.c Me refined with riding coordinates:
 C85(H85A,H85B,H85C), C97(H97A,H97B,H97C), C97A(H97D,H97E,H97F), C35(H35A,H35B,
 H35C), C47(H47A,H47B,H47C)
6.d Aromatic/amide H refined with riding coordinates:
 C56(H56), C57(H57), C58(H58), C59(H59), C63(H63), C65(H65), C73(H73),
 C75(H75), C77(H77), C78(H78), C79(H79), C87(H87), C88(H88), C89(H89), C90(H90),
  C91(H91), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C15(H15), C23(H23),
 C25(H25), C27(H27), C28(H28), C29(H29), C37(H37), C39(H39), C40(H40), C41(H41)
;
_shelx_res_checksum              16786
_shelx_hkl_checksum              60038
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id 'Sample #21: m-ITIC'
_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 2.046
_oxdiff_exptl_absorpt_empirical_full_min 0.503