High-Performance Simple Nonfused Ring Electron Acceptors with Diphenylamino Flanking Groups.
Wang, Xiaodong; Lu, Hao; Zhou, Jiadong; Xu, Xiaoyun; Zhang, Cai'e; Huang, Hao; Song, Jinsheng; Liu, Yahui; Xu, Xinjun; Xie, Zengqi; Tang, Zheng; Bo, Zhishan; ACS applied materials & interfaces 13 (2021) 39652–39659; doi:10.1021/acsami.1c09597

data_4518951
_publ_section_title
;
 High-Performance Simple Nonfused Ring Electron Acceptors with
 Diphenylamino Flanking Groups.
;
_journal_issue                   33
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              39652
_journal_page_last               39659
_journal_paper_doi               10.1021/acsami.1c09597
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C78 H36 F4 N6 O2 S4'
_chemical_formula_sum            'C78 H36 F4 N6 O2 S4'
_chemical_formula_weight         1293.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           50
_space_group_name_Hall           '-P 2ab 2b'
_space_group_name_H-M_alt        'P b a n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0496(8)
_cell_length_b                   28.0149(11)
_cell_length_c                   35.322(5)
_cell_measurement_reflns_used    4206
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      67.5430
_cell_measurement_theta_min      3.1850
_cell_volume                     15882(2)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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    -10.00  33.00   0.50   10.00    --    0.00  57.00-120.00   86
  2  \w    -62.00 -37.00   0.50   10.00    --    0.00 -19.00-150.00   50
  3  \w    -87.00  12.00   0.50   10.00    --    0.00 -72.00  30.00  198
  4  \w      4.00  66.00   0.50   10.00    --    0.00  57.00 -30.00  124
  5  \w     40.00  88.00   0.50   10.00    --    0.00  57.00-120.00   96
  6  \w    -87.00  12.00   0.50   10.00    --    0.00 -19.00  90.00  198
  7  \w   -112.00 -13.00   0.50   40.00    --  -98.80  72.00 -30.00  198
  8  \w    -94.00 -62.00   0.50   40.00    --  -98.80  72.00 150.00   64
  9  \w    -57.00 -25.00   0.50   40.00    --  -98.80  72.00-120.00   64
 10  \w   -112.00 -29.00   0.50   40.00    --  -98.80  72.00  30.00  166
 11  \w   -113.00 -51.00   0.50   40.00    --  -98.80  72.00-150.00  124
 12  \w    -47.00 -15.00   0.50   40.00    --  -98.80  57.00 -30.00   64
 13  \w    -95.00 -68.00   0.50   40.00    --  -98.80  72.00  90.00   54
 14  \w   -111.00 -37.00   0.50   40.00    --  -98.80  57.00 150.00  148
 15  \w   -112.00 -18.00   0.50   40.00    --  -98.80  19.00-150.00  188
 16  \w   -112.00 -60.00   0.50   40.00    --  -98.80  72.00 -90.00  104
 17  \w   -112.00 -41.00   0.50   40.00    --  -98.80  72.00   0.00  142
 18  \w   -112.00 -10.00   0.50   40.00    --  -98.80  19.00 -60.00  204
 19  \w   -108.00 -18.00   0.50   40.00    --  -98.80  72.00  60.00  180
 20  \w    -95.00 -69.00   0.50   40.00    --  -98.80  19.00  90.00   52
 21  \w    -50.00 -10.00   0.50   40.00    --  -98.80  19.00  90.00   80
 22  \w    -75.00 -54.00   0.50   40.00    --  -98.80  72.00-180.00   42
;
_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      -0.0016958000
_diffrn_orient_matrix_UB_12      0.0435291000
_diffrn_orient_matrix_UB_13      0.0057681000
_diffrn_orient_matrix_UB_21      0.0285066000
_diffrn_orient_matrix_UB_22      0.0029775000
_diffrn_orient_matrix_UB_23      -0.0816163000
_diffrn_orient_matrix_UB_31      -0.0470216000
_diffrn_orient_matrix_UB_32      0.0001527000
_diffrn_orient_matrix_UB_33      -0.0500735000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2623
_diffrn_reflns_av_unetI/netI     0.1441
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            118423
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         2.502
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53377
_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_density_diffrn    0.541
_exptl_crystal_description       plate
_exptl_crystal_F_000             2648
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.066
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         14104
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1841
_refine_ls_R_factor_gt           0.1142
_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          0.2983
_refine_ls_wR_factor_ref         0.3514
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5906
_reflns_number_total             14104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am1c09597_si_001.cif
_cod_data_source_block           ch3_2f
_cod_original_sg_symbol_H-M      'P b a n'
_cod_database_code               4518951
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C00I-C016 = C016-C01A = C01A-C01E = C01E-C4
 1.5 with sigma of 0.01
 C00I-C01A = C016-C01E = C01A-C4
 2.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C00A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00G(H00G), C00K(H00K), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C010(H010), C011(H011), C012(H012), C014(H014), C015(H015), C018(H018)
4.b Idealised Me refined as rotating group:
 C017(H01A,H01B,H01C), C019(H01D,H01E,H01F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              65609
_shelx_hkl_checksum              78465
_shelx_fab_checksum              13533
_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 1.738
_oxdiff_exptl_absorpt_empirical_full_min 0.418