Isomeric Effect in Unidirectionally Extended Fused-Ring Electron Acceptors
Jia, Boyu; Li, Mengyang; Zhou, Jiadong; Xiao, Yiqun; Zhang, Shenghan; Wang, Jiayu; Lu, Xinhui; Xie, Zengqi; Tang, Zheng; Zhan, Xiaowei; Chemistry of Materials  (2020) –; doi:10.1021/acs.chemmater.0c04318

data_4003844
_publ_section_title
;
 Isomeric Effect in Unidirectionally Extended Fused-Ring Electron
 Acceptors
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c04318
_journal_year                    2020
_chemical_formula_moiety
'0.5(C116 H90 F4 N4 O2 S4), 0.5(C116 H96 F4 N4 O2 S4)'
_chemical_formula_sum            'C116 H93 F4 N4 O2 S4'
_chemical_formula_weight         1779.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.789(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.301(3)
_cell_length_b                   37.511(5)
_cell_length_c                   27.083(5)
_cell_measurement_reflns_used    8699
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      48.3430
_cell_measurement_theta_min      2.6300
_cell_volume                     21905(6)
_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 0.988
_diffrn_measured_fraction_theta_max 0.942
_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    -79.00 -43.00   0.50    5.00    --    0.00 -57.00 -30.00   72
  2  \w    -61.00  10.00   0.50    5.00    --    0.00 -57.00-180.00  142
  3  \w    -77.00 -52.00   0.50    5.00    --    0.00 -37.00-150.00   50
  4  \w     17.00  94.00   0.50   20.00    --    5.00  37.00 -60.00  154
  5  \w   -112.00 -75.00   0.50   20.00    --  -98.80  72.00 -90.00   74
  6  \w    -71.00 -38.00   0.50   20.00    --  -98.80  72.00 -90.00   66
  7  \w   -113.00 -85.00   0.50   20.00    --  -98.80 -72.00  90.00   56
  8  \w   -113.00 -78.00   0.50   20.00    --  -98.80  72.00 -60.00   70
  9  \w   -180.00 -85.00   0.50   20.00    --  -98.80 -19.00-120.00  190
 10  \w    -64.00 -13.00   0.50   20.00    --  -98.80  72.00 -60.00  102
 11  \w   -185.00-156.00   0.50   20.00    --  -98.80 -72.00  60.00   58
 12  \w   -125.00 -99.00   0.50   20.00    --  -98.80 -72.00  60.00   52
 13  \w   -188.00 -87.00   0.50   20.00    --  -98.80 -37.00-150.00  202
 14  \w    -86.00 -60.00   0.50   20.00    --  -98.80  72.00   0.00   52
 15  \w   -112.00 -16.00   0.50   20.00    --  -98.80  72.00 -30.00  192
 16  \w   -168.00 -92.00   0.50   20.00    --  -98.80 -72.00-180.00  152
 17  \w    -91.00 -17.00   0.50   20.00    --  -98.80  37.00 -30.00  148
;
_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      0.0474919000
_diffrn_orient_matrix_UB_12      -0.0012635000
_diffrn_orient_matrix_UB_13      -0.0325858000
_diffrn_orient_matrix_UB_21      0.0136303000
_diffrn_orient_matrix_UB_22      -0.0394417000
_diffrn_orient_matrix_UB_23      0.0143133000
_diffrn_orient_matrix_UB_31      -0.0518009000
_diffrn_orient_matrix_UB_32      -0.0109297000
_diffrn_orient_matrix_UB_33      -0.0469390000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.1044
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            127363
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.486
_diffrn_reflns_theta_min         2.582
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32574
_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    1.079
_exptl_crystal_description       plate
_exptl_crystal_F_000             7464
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2347
_refine_ls_number_reflns         42174
_refine_ls_number_restraints     173
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.2159
_refine_ls_R_factor_gt           0.1204
_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          0.3250
_refine_ls_wR_factor_ref         0.3910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14280
_reflns_number_total             42174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm0c04318_si_002.cif
_cod_data_source_block           aoic
_cod_database_code               4003844
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.02
_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
 C2AA-C3AA
 2.45 with sigma of 0.01
 C5-C4AA
 2.45 with sigma of 0.01
 C3AA-C4AA
 1.5 with sigma of 0.01
 C5AA-C4 = C4-C6AA = C6AA-C7AA = C7AA-C8AA
 1.5 with sigma of 0.01
 C068-C3 = C3-C9AA = C9AA-C25 = C25-C6 = C6-C0BA
 1.5 with sigma of 0.01
 C25-C0BA
 2.45 with sigma of 0.01
3. Rigid bond restraints
 C065, C5, C2AA, C3AA, C4AA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C068, C3, C9AA, C25, C6, C0BA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C05W) \\sim Ueq, Uanis(C0AA) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C1AA) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C06G) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C065) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C2AA) \\sim Ueq, Uanis(C3AA)
\\sim Ueq, Uanis(C4AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C5AA) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6AA) \\sim Ueq, Uanis(C7AA)
\\sim Ueq, Uanis(C8AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C068) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C9AA) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C0BA) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C03N(H03A,H03B), C03S(H03D,H03F), C045(H04A,H04B), C046(H04C,H04D), C04J(H04E,
 H04F), C04Q(H04G,H04H), C04U(H04I,H04J), C04V(H04L,H04M), C050(H05A,H05B),
 C052(H05C,H05D), C055(H05E,H05F), C05H(H1AA,H), C05J(H2AA,HA), C05L(H05P,H05Q),
  C05P(H05R,H05S), C05S(H6AA,HB), C05T(H05U,H05V), C05U(H05W,H05X), C05W(H8AA,
 HC), C05Z(H05Z,HD), C063(H06A,H06B), C065(H06X,H06Y), C067(H06C,H06D),
 C068(H06Z,HE), C06A(H06E,H06F), C06B(H06G,H06H), C06C(H06,HF), C06E(H06I,H06J),
  C06H(H06N,H06O), C06I(H0BA,HG), C06J(H1BA,HH), C06K(H06P,H06Q), C072(H07A,
 H07B), C18(H18A,H18B), C5(H5A,H5B), C0AA(H0AB,H0AC), C10(H10A,H10B), C7(H7A,
 H7B), C1(H1A,H1B), C2AA(H2AB,H2AC), C3AA(H3AB,H3AC), C12(H12A,H12B), C5AA(H5AB,
 H5AC), C3(H3A,H3B), C4(H4A,H4B), C6AA(H6AB,H6AC), C7AA(H7AB,H7AC), C6(H6A,H6B),
  C9AA(H9AB,H9AC), C25(H25A,H25B)
5.b Aromatic/amide H refined with riding coordinates:
 C00W(H00W), C00Y(H00Y), C017(H017), C01A(H01A), C01B(H01B), C01C(H01C),
 C01F(H01F), C01O(H01O), C01X(H01X), C01Y(H01Y), C020(H020), C027(H027),
 C028(H028), C02B(H02B), C02D(H02D), C02H(H02H), C02K(H02K), C02M(H02M),
 C02P(H02P), C02V(H02V), C02Y(H02Y), C030(H030), C032(H032), C038(H038),
 C039(H039), C03C(H03C), C03E(H03E), C03H(H03H), C03I(H03I), C03K(H03K),
 C03Q(H03Q), C03R(H03R), C03U(H03U), C03V(H03V), C03W(H03W), C03Y(H03Y),
 C041(H041), C043(H043), C044(H044), C048(H048), C04D(H04O), C04K(H04K),
 C04M(H04P), C04N(H04N), C04P(H04Q), C04R(H04R), C04S(H04S), C04T(H04T),
 C04X(H04X), C04Y(H04Y), C053(H053), C057(H057), C058(H058), C059(H059),
 C05A(H05), C05C(H0AA), C05D(H05J), C05F(H05N), C05G(H05O), C05N(H3AA),
 C05O(H4AA), C05Q(H5AA), C05R(H05T), C05V(H7AA), C05X(H05Y), C05Y(H9AA),
 C061(H061), C064(H064)
5.c Idealised Me refined as rotating group:
 C056(H05G,H05H,H05I), C05E(H05K,H05L,H05M), C060(H06U,H06V,H06W), C06F(H06K,
 H06L,H06M), C06T(H06R,H06S,H06T), C1AA(H1AB,H1AC,H1AD)
;
_shelx_res_checksum              12348
_shelx_hkl_checksum              69548
_shelx_fab_checksum              7994
_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 3.633
_oxdiff_exptl_absorpt_empirical_full_min 0.452