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_4003846
_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      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             2020-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.580(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4700(5)
_cell_length_b                   19.6160(6)
_cell_length_c                   35.4927(9)
_cell_measurement_reflns_used    8486
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      68.4130
_cell_measurement_theta_min      2.5370
_cell_volume                     10064.2(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     18.00  43.00   0.50   20.00    --    5.00  27.00-144.00   50
  2  \w    -33.00  -8.00   0.50   20.00    --    5.00 -27.00  52.00   50
  3  \w   -163.00-101.00   0.50   20.00    --  -98.80 -27.00  52.00  124
  4  \w    -86.00 -60.00   0.50   20.00    --  -98.80  27.00-144.00   52
  5  \w    -88.00 -34.00   0.50    5.00    --    0.00 -37.00 -60.00  108
  6  \w    -26.00  13.00   0.50    5.00    --    0.00 -37.00 -60.00   78
  7  \w    -88.00  12.00   0.50    5.00    --    0.00 -57.00-180.00  200
  8  \w    -48.00 -14.00   0.50    5.00    --    0.00 -57.00-120.00   68
  9  \w   -185.00 -88.00   0.50   20.00    --  -98.80 -37.00  90.00  194
 10  \w   -187.00-136.00   0.50   20.00    --  -98.80 -72.00-180.00  102
 11  \w   -186.00 -85.00   0.50   20.00    --  -98.80 -19.00 -30.00  202
 12  \w   -105.00 -67.00   0.50   20.00    --  -98.80  72.00 -30.00   76
 13  \w   -104.00 -20.00   0.50   20.00    --  -98.80  72.00 -90.00  168
 14  \w   -106.00 -20.00   0.50   20.00    --  -98.80  37.00-120.00  172
 15  \w   -112.00 -41.00   0.50   20.00    --  -98.80  72.00  60.00  142
 16  \w    -57.00  -9.00   0.50   20.00    --  -98.80  37.00 -30.00   96
 17  \w    -86.00 -28.00   0.50   20.00    --  -98.80  57.00   0.00  116
;
_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      0.0807790000
_diffrn_orient_matrix_UB_12      -0.0191245000
_diffrn_orient_matrix_UB_13      -0.0247658000
_diffrn_orient_matrix_UB_21      0.0694912000
_diffrn_orient_matrix_UB_22      0.0196260000
_diffrn_orient_matrix_UB_23      0.0323056000
_diffrn_orient_matrix_UB_31      -0.0022447000
_diffrn_orient_matrix_UB_32      -0.0736169000
_diffrn_orient_matrix_UB_33      0.0151640000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            56658
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         2.492
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59818
_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    1.226
_exptl_crystal_description       plate
_exptl_crystal_F_000             3928
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.215
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1241
_refine_ls_number_reflns         17952
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0952
_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^)+(0.1329P)^2^+13.6379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2540
_refine_ls_wR_factor_ref         0.2890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10437
_reflns_number_total             17952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm0c04318_si_002.cif
_cod_data_source_block           aoic2
_cod_database_code               4003846
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.923
_reflns_odcompleteness_completeness 99.84
_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. Restrained distances
 C02Y-C1 = C1-C1AA = C1AA-C0AA
 1.5 with sigma of 0.01
 C03I-C03G = C03G-C03H = C03H-C2 = C2-C03O
 1.5 with sigma of 0.01
 C03F-C3 = C3-C03J
 1.5 with sigma of 0.01
3. Others
 Sof(HA)=Sof(HB)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H0AD)=Sof(H0AE)=Sof(C1AA)=
 Sof(H1AB)=Sof(H1AC)=1-FVAR(1)
 Sof(H02Z)=Sof(H)=Sof(C03L)=Sof(H1AA)=Sof(HK)=Sof(H0AB)=Sof(H0AC)=Sof(C4)=
 Sof(H4A)=Sof(H4B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C02K(H02C,H02D), C02L(H02H,H02I), C02N(H02J,H02K), C02O(H02L,H02N), C02U(H02O,
 H02Q), C02V(H02S,H02U), C02W(H02V,H02W), C02X(H02X,H02Y), C02Y(H02Z,H),
 C02Y(HA,HB), C030(H03A,H03B), C031(H03C,H03D), C032(H03E,H03F), C034(H03G,
 H03H), C036(H03I,H03J), C037(H03K,H03L), C038(H03M,H03N), C03A(H03O,H03P),
 C03B(H03Q,H03R), C03D(H03S,H03T), C03F(H03U,H03V), C03G(H03W,H03X), C03H(H03Y,
 HE), C03I(H03Z,HF), C03L(H1AA,HK), C03N(H3AA,HN), C2(H2A,H2B), C3(H3A,H3B),
 C1(H1A,H1B), C0AA(H0AB,H0AC), C0AA(H0AD,H0AE), C4(H4A,H4B), C1AA(H1AB,H1AC),
 C2AA(H2AB,H2AC)
4.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00L(H00L), C00Q(H00Q), C00Y(H00Y), C010(H010), C012(H012),
 C015(H015), C016(H016), C017(H017), C018(H018), C01C(H01C), C01D(H01D),
 C01G(H01G), C01M(H01M), C01N(H01N), C01O(H01O), C01T(H01T), C01V(H01V),
 C01X(H01X), C01Y(H01Y), C01Z(H01Z), C020(H020), C022(H022), C024(H024),
 C029(H029), C02A(H02A), C02B(H02B), C02E(H02E), C02F(H02F), C02G(H02G),
 C02M(H02M), C02P(H02P), C02R(H02R), C02T(H02T)
4.c Idealised Me refined as rotating group:
 C02Z(H02,HC,HD), C03J(H03,HG,HH), C03K(H0AA,HI,HJ), C03M(H2AA,HL,HM),
 C03O(H4AA,HO,HP), C3AA(H3AB,H3AC,H3AD)
;
_shelx_res_checksum              90321
_shelx_hkl_checksum              96738
_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 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.556