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_1552929
_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
'C49 H49 N2 O3 S2, C49 H48 N2 O3 S2, 2(C3 H6 O)'
_chemical_formula_sum            'C104 H109 N4 O8 S4'
_chemical_formula_weight         1671.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 89.997(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2836(2)
_cell_length_b                   20.0101(5)
_cell_length_c                   29.3242(6)
_cell_measurement_reflns_used    8815
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.4000
_cell_measurement_theta_min      2.9900
_cell_volume                     8968.1(3)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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    -63.00 -20.00   0.50    5.00    --    0.00  20.00-180.00   86
  2  \w    -15.00  73.00   0.50    5.00    --    0.00  20.00-180.00  176
  3  \w   -100.00 -61.00   0.50   30.00    --  -90.00  59.00 -22.72   78
  4  \w   -179.00-122.00   0.50   30.00    --  -90.00  56.00  93.75  114
  5  \w   -136.00 -14.00   0.50   30.00    --  -90.00  58.00-177.24  244
  6  \w   -177.00-146.00   0.50   30.00    --  -90.00  59.00 122.03   62
  7  \w   -160.00  -4.00   0.50   30.00    --  -90.00  59.00-138.62  312
  8  \w    -50.00 -25.00   0.50   30.00    --  -90.00  59.00 163.27   50
  9  \w    -85.00  -1.00   0.50   30.00    --  -90.00  59.00 122.03  168
 10  \w    -38.00  -2.00   0.50   30.00    --  -90.00  56.00  93.75   72
 11  \w   -178.00 -22.00   0.50   30.00    --  -90.00  59.00-169.54  312
 12  \w   -178.00-145.00   0.50   30.00    --  -90.00  59.00 154.04   66
 13  \w   -162.00-134.00   0.50   30.00    --  -90.00  59.00 163.27   56
 14  \w   -123.00 -85.00   0.50   30.00    --  -90.00  59.00 163.27   76
 15  \w   -136.00-111.00   0.50   30.00    --  -90.00  59.00 -22.72   50
 16  \w   -135.00 -74.00   0.50   30.00    --  -90.00  58.00-119.97  122
;
_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      0.0048336000
_diffrn_orient_matrix_UB_12      0.0615427000
_diffrn_orient_matrix_UB_13      0.0313809000
_diffrn_orient_matrix_UB_21      0.0151373000
_diffrn_orient_matrix_UB_22      -0.0460157000
_diffrn_orient_matrix_UB_23      0.0414341000
_diffrn_orient_matrix_UB_31      0.0995411000
_diffrn_orient_matrix_UB_32      0.0039173000
_diffrn_orient_matrix_UB_33      -0.0078460000
_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  0.0953
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            62183
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         2.208
_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    1.446
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69242
_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            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       rod
_exptl_crystal_F_000             3556
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of chloroform and acetone'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1174
_refine_ls_number_reflns         15523
_refine_ls_number_restraints     2209
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.0998
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1195P)^2^+19.4910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2395
_refine_ls_wR_factor_ref         0.2842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9046
_reflns_number_total             15523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9mh01439j2.cif
_cod_data_source_block           4TICO
_cod_depositor_comments
;Adding full bibliography for 1552926--1552934.cif.

 Adding full bibliography for 1552926--1552934.cif.
;
_cod_database_code               1552929
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C98 H82 N4 O6 S4'
_chemical_oxdiff_usercomment
'Sample #10: OPN018 Chloroform/Acetone recollection'
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.751
_reflns_odcompleteness_completeness 97.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.452(4)
 0.548(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C36-C35
 -1.4 with sigma of 0.02
 C99-C98 = C98-C97 = C97-C96 = C96-C95 = C95-C94 = C94-C93 = C93-C92
 1.5 with sigma of 0.03
 O201-C201 \\sim O211-C211
 with sigma of 0.02
 O211-C211 \\sim O216-C216
 with sigma of 0.02
 O52-C84 \\sim O3-C42 \\sim O2-C34 \\sim O53-C92
 with sigma of 0.02
 O52-C85 \\sim O3-C43 \\sim O2-C35 \\sim O53-C93
 with sigma of 0.02
 C25-C34 \\sim C31-C42 \\sim C75-C84 \\sim C81-C92
 with sigma of 0.02
 C93-C94 \\sim C93-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 C93-C95A
 with sigma of 0.04
 C94-C96 \\sim C94A-C96A
 with sigma of 0.04
 C96-C98 \\sim C96A-C98A
 with sigma of 0.04
 C94A-C92 \\sim C92-C94
 with sigma of 0.04
 C202-O201 \\sim C203-O201 \\sim C213-O211 \\sim O211-C212
 with sigma of 0.04
 C213-C211 \\sim C211-C212 \\sim C202-C201 \\sim C203-C201
 with sigma of 0.02
 C202-C203 \\sim C213-C212
 with sigma of 0.04
 C211-C212 \\sim C216-C217
 with sigma of 0.02
 C211-C213 \\sim C216-C218
 with sigma of 0.02
 O211-C212 \\sim O216-C217
 with sigma of 0.04
 O211-C213 \\sim O216-C218
 with sigma of 0.04
 C212-C213 \\sim C217-C218
 with sigma of 0.04
 C34-C35 \\sim C35-C36 \\sim C36-C37 \\sim C37-C38 \\sim C38-C39 \\sim C39-C40
\\sim C40-C41
 with sigma of 0.02
 C38-C40 \\sim C35-C37 \\sim C37-C39 \\sim C39-C41 \\sim C34-C36 \\sim C36-C38
 with sigma of 0.04
 C91-C90 \\sim C90-C89 \\sim C89-C88 \\sim C88-C87 \\sim C87-C86 \\sim C86-C85
\\sim C85-C84
 with sigma of 0.02
 C91-C89 \\sim C89-C87 \\sim C87-C85 \\sim C90-C88 \\sim C88-C86 \\sim C86-C84
 with sigma of 0.04
 C43-C44 \\sim C44-C45 \\sim C45-C46 \\sim C46-C47 \\sim C47-C48 \\sim C48-C49
\\sim C43-C42
 with sigma of 0.02
 C44-C46 \\sim C46-C48 \\sim C43-C45 \\sim C45-C47 \\sim C47-C49 \\sim C42-C44
 with sigma of 0.04
 C96-C97 \\sim C96A-C97A
 with sigma of 0.02
 C97-C98 \\sim C97A-C98A
 with sigma of 0.02
 C95-C97 \\sim C95A-C97A
 with sigma of 0.04
 C99-C98 \\sim C98-C97 \\sim C97-C96 \\sim C96-C95 \\sim C95-C94 \\sim C94-C93
\\sim C93-C92
 with sigma of 0.02
 C99-C97 \\sim C97-C95 \\sim C95-C93 \\sim C98-C96 \\sim C96-C94 \\sim C94-C92
 with sigma of 0.04
 C98-C99 \\sim C98A-C99A
 with sigma of 0.02
 C97-C99 \\sim C97A-C99A
 with sigma of 0.04
4. 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
5. 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
6. Others
 Sof(O216)=Sof(C216)=Sof(C217)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C218)=
 Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(O211)=Sof(C211)=Sof(C212)=Sof(H21G)=Sof(H21H)=Sof(H21I)=Sof(C213)=
 Sof(H21J)=Sof(H21K)=Sof(H21L)=FVAR(1)
 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(H97C)=Sof(H97D)=
 Sof(C98A)=Sof(H98C)=Sof(H98D)=Sof(C99A)=Sof(H99D)=Sof(H99E)=Sof(H99F)=1-FVAR(2)
 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(C98)=Sof(H98A)=
 Sof(H98B)=Sof(C99)=Sof(H99A)=Sof(H99B)=Sof(H99C)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C65(H65A,H65B), C84(H84A,H84B), C85(H85A,H85B), C86(H86A,H86B), C87(H87A,
 H87B), C88(H88A,H88B), C89(H89A,H89B), C90(H90A,H90B), C92(H92A,H92B),
 C93(H93A,H93B), C93(H93C,H93D), C94(H94A,H94B), C95(H95A,H95B), C96(H96A,H96B),
  C97(H97A,H97B), C98(H98A,H98B), C94A(H94C,H94D), C95A(H95C,H95D), C96A(H96C,
 H96D), C97A(H97C,H97D), C98A(H98C,H98D), C34(H34A,H34B), C35(H35A,H35B),
 C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B),
  C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,
 H46B), C47(H47A,H47B), C48(H48A,H48B)
7.b Me refined with riding coordinates:
 C91(H91A,H91B,H91C), C99(H99A,H99B,H99C), C99A(H99D,H99E,H99F), C41(H41A,H41B,
 H41C), C49(H49A,H49B,H49C), C217(H21A,H21B,H21C), C218(H21D,H21E,H21F),
 C202(H20A,H20B,H20C), C203(H20D,H20E,H20F), C212(H21G,H21H,H21I), C213(H21J,
 H21K,H21L)
7.c Aromatic/amide H refined with riding coordinates:
 C56(H56), C57(H57), C58(H58), C59(H59), C63(H63), C73(H73), C74(H74),
 C76(H76), C77(H77), C79(H79), C80(H80), C82(H82), C83(H83), C6(H6), C7(H7),
 C8(H8), C9(H9), C13(H13), C15(H15), C23(H23), C24(H24), C26(H26), C27(H27),
 C29(H29), C30(H30), C32(H32), C33(H33)
;
_shelx_res_checksum              99655
_shelx_hkl_checksum              74434
_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 #10:OPN018'
_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 2.519
_oxdiff_exptl_absorpt_empirical_full_min 0.690