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_4003845
_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         'C121 H112 F4 N4 O2 S4'
_chemical_formula_sum            'C121 H112 F4 N4 O2 S4'
_chemical_formula_weight         1858.38
_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             2020-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                77.309(7)
_cell_angle_beta                 88.059(8)
_cell_angle_gamma                90.002(8)
_cell_formula_units_Z            2
_cell_length_a                   10.7771(14)
_cell_length_b                   18.5061(15)
_cell_length_c                   26.1941(18)
_cell_measurement_reflns_used    3365
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      69.2600
_cell_measurement_theta_min      2.5410
_cell_volume                     5093.5(9)
_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      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.828
_diffrn_measured_fraction_theta_max 0.828
_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     14.00  61.00   0.50    8.00    --    0.00  48.00  -0.00   94
  2  \w    -57.00 -32.00   0.50   32.00    --    5.00 -48.00-148.00   50
  3  \w     18.00  43.00   0.50   32.00    --    5.00  48.00  -0.00   50
  4  \w    -45.00 -13.00   0.50   32.00    --  -99.50  48.00  -0.00   64
  5  \w   -106.00 -79.00   0.50   32.00    --  -99.50  48.00  -0.00   54
  6  \w   -153.00-126.00   0.50   32.00    --  -99.50 -48.00-148.00   54
  7  \w    -44.00 -10.00   0.50    8.00    --    0.00 -48.00-148.00   68
  8  \w    -89.00 -32.00   0.50    8.00    --    0.00 -19.00  90.00  114
  9  \w    -88.00  12.00   0.50    8.00    --    0.00 -37.00   0.00  200
 10  \w    -86.00 -35.00   0.50    8.00    --    0.00 -57.00 150.00  102
 11  \w   -106.00 -79.00   0.50   32.00    --  -99.50  57.00-120.00   54
 12  \w   -188.00-114.00   0.50   32.00    --  -99.50 -19.00 -90.00  148
 13  \w   -188.00 -87.00   0.50   32.00    --  -99.50 -37.00-120.00  202
 14  \w    -49.00 -21.00   0.50   32.00    --  -99.50  72.00-150.00   56
 15  \w   -112.00 -23.00   0.50   32.00    --  -99.50  57.00-180.00  178
 16  \w   -108.00 -12.00   0.50   32.00    --  -99.50  57.00  30.00  192
 17  \w    -84.00 -57.00   0.50   32.00    --  -99.50  72.00-150.00   54
 18  \w   -111.00 -19.00   0.50   32.00    --  -99.50  72.00   0.00  184
 19  \w    -50.00 -25.00   0.50   32.00    --  -99.50  57.00-120.00   50
 20  \w   -102.00 -34.00   0.50   32.00    --  -99.50  37.00-180.00  136
;
_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      0.0245204000
_diffrn_orient_matrix_UB_12      0.0137753000
_diffrn_orient_matrix_UB_13      -0.0596495000
_diffrn_orient_matrix_UB_21      -0.0811820000
_diffrn_orient_matrix_UB_22      -0.0678030000
_diffrn_orient_matrix_UB_23      -0.0019017000
_diffrn_orient_matrix_UB_31      -0.1152283000
_diffrn_orient_matrix_UB_32      0.0499477000
_diffrn_orient_matrix_UB_33      -0.0087748000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.1166
_diffrn_reflns_Laue_measured_fraction_full 0.828
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27714
_diffrn_reflns_point_group_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         2.447
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77760
_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    1.212
_exptl_crystal_description       plate
_exptl_crystal_F_000             1964
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.066
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1250
_refine_ls_number_reflns         15063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.221
_refine_ls_R_factor_all          0.2550
_refine_ls_R_factor_gt           0.1558
_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^)+(0.3000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4464
_refine_ls_wR_factor_ref         0.5260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6678
_reflns_number_total             15063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm0c04318_si_002.cif
_cod_data_source_block           aoic1
_cod_database_code               4003845
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 83.12
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H02S)=Sof(H02T)=Sof(HK)=Sof(HL)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C5)=
 Sof(H5A)=Sof(H5B)=Sof(C18)=Sof(H18A)=Sof(H18B)=1-FVAR(1)
 Sof(H02P)=Sof(H02Q)=Sof(H3AA)=Sof(HJ)=Sof(C03P)=Sof(H8AA)=Sof(HR)=Sof(C4)=
 Sof(H4A)=Sof(H4B)=Sof(C19)=Sof(H19A)=Sof(H19B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C02C(H02B,H02C), C02F(H02F,H02G), C02K(H02J,H02K), C02Q(H02L,H02N), C02S(H02P,
 H02Q), C02S(H02S,H02T), C02T(H02U,H02V), C02X(H02X,H02Y), C02Y(H02Z,H),
 C02Z(H02,HA), C030(H03A,H03B), C031(H03C,H03D), C032(H03E,H03F), C034(H03G,
 H03H), C035(H03I,H03J), C036(H03K,H03L), C038(H03M,H03N), C03A(H03R,H03S),
 C03B(H03T,H03U), C03C(H03V,H03W), C03D(H03X,H03Y), C03F(H03,HD), C03G(H0AA,HE),
  C03J(H3AA,HJ), C03J(HK,HL), C03K(H4AA,HM), C03L(H5AA,HN), C03M(H6AA,HO),
 C03P(H8AA,HR), C13(H13A,H13B), C03S(H0BA,HU), C4(H4A,H4B), C19(H19A,H19B),
 C5(H5A,H5B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00I(H00I), C00K(H00K), C00L(H00L), C00N(H00N), C00Q(H00Q),
 C00R(H00R), C00T(H00T), C00U(H00U), C00W(H00W), C00X(H00X), C014(H014),
 C018(H018), C01A(H01A), C01D(H01D), C01K(H01K), C01M(H01M), C01O(H01O),
 C01Q(H01Q), C01T(H01T), C01Z(H01Z), C021(H021), C024(H024), C027(H027),
 C029(H029), C02A(H02A), C02D(H02D), C02E(H02E), C02G(H02H), C02H(H02I),
 C02M(H02M), C02O(H02O), C02R(H02R), C02W(H02W)
3.c Idealised Me refined as rotating group:
 C039(H03O,H03P,H03Q), C03E(H03Z,HB,HC), C03H(H1AA,HF,HG), C03I(H2AA,HH,HI),
 C03O(H7AA,HP,HQ), C03R(H9AA,HS,HT)
;
_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 2.133
_oxdiff_exptl_absorpt_empirical_full_min 0.468