Perylene Five-membered Ring Diimide for Organic Semiconductors and π-Expanded Conjugated Molecules
Chen, Liangliang; Wu, Botao; Qin, Liyuan; Huang, Yan-Ying; Meng, Wei; Kong, Ruirui; Yu, Xiaobo; ChenChai, Kaiyuan; Li, Cheng; Zhang, Guanxin; Zhang, Xisha; Zhang, Deqing; Chemical Communications  (2022) –; doi:10.1039/D2CC01061E

data_7129896
_publ_section_title
;
 Perylene Five-membered Ring Diimide for Organic Semiconductors and
 \p-Expanded Conjugated Molecules
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01061E
_journal_year                    2022
_chemical_formula_moiety         '3(C32 H29 N O2)'
_chemical_formula_sum            'C96 H87 N3 O6'
_chemical_formula_weight         1378.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-01 deposited with the CCDC.	2022-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.469(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   40.9622(10)
_cell_length_b                   10.7321(2)
_cell_length_c                   39.9989(10)
_cell_measurement_reflns_used    10556
_cell_measurement_temperature    169.99(14)
_cell_measurement_theta_max      74.0480
_cell_measurement_theta_min      2.1720
_cell_volume                     16004.6(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.954
_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      7.00  34.00   0.50   18.00    --   47.20 -42.00 -71.00   54
  2  \w     31.00  96.00   0.50   51.27    --  103.25 -94.00  30.00  130
  3  \w     55.00 105.00   0.50   51.27    --  103.25 -94.00 120.00  100
  4  \w     32.00 105.00   0.50   51.27    --  103.25 -94.00  60.00  146
  5  \w     34.00  75.00   0.50   51.27    --  103.25 -61.00-120.00   82
  6  \w    101.00 169.00   0.50   51.27    --  103.25  30.00   0.00  136
  7  \w    136.00 169.00   0.50   51.27    --  103.25 125.00 -60.00   66
  8  \w     89.00 115.00   0.50   18.00    --   47.20  42.00  81.00   52
  9  \w     97.00 140.00   0.50   51.27    --  103.25  42.00  81.00   86
 10  \w     89.00 122.00   0.50   51.27    --  103.25 125.00 -60.00   66
 11  \w     37.00  77.00   0.50   18.00    --   47.20  42.00  81.00   80
 12  \w    -10.00  15.00   0.50   18.00    --  -47.20  42.00  81.00   50
 13  \w    -57.00 -31.00   0.50   51.27    --  -99.00  77.00 -30.00   52
 14  \w    -12.00  28.00   0.50   18.00    --  -47.20  19.00-120.00   80
 15  \w    -22.00  27.00   0.50   18.00    --  -47.20  19.00-150.00   98
 16  \w    -60.00 -32.00   0.50   51.27    --  -99.00  61.00-150.00   56
 17  \w    -58.00 -31.00   0.50   51.27    --  -99.00  61.00-180.00   54
 18  \w    -65.00 -37.00   0.50   51.27    --  -99.00  61.00-120.00   56
 19  \w    -94.00 -63.00   0.50   51.27    --  -99.00  77.00 -30.00   62
 20  \w   -101.00 -29.00   0.50   51.27    --  -99.00  77.00 -90.00  144
 21  \w   -109.00 -36.00   0.50   18.00    --  -47.20 -42.00 -71.00  146
 22  \w    -64.00 -33.00   0.50   51.27    --  -99.00  61.00 150.00   62
 23  \w    -66.00 -26.00   0.50   51.27    --  -99.00  61.00 120.00   80
 24  \w   -152.00 -95.00   0.50   51.27    --  -99.00 -42.00 -71.00  114
 25  \w   -119.00 -76.00   0.50   18.00    --  -47.20-125.00  30.00   86
 26  \w   -120.00 -95.00   0.50   18.00    --  -47.20-125.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0215740000
_diffrn_orient_matrix_UB_12      -0.1224397000
_diffrn_orient_matrix_UB_13      -0.0097641000
_diffrn_orient_matrix_UB_21      -0.0020843000
_diffrn_orient_matrix_UB_22      0.0072349000
_diffrn_orient_matrix_UB_23      -0.0392969000
_diffrn_orient_matrix_UB_31      0.0351778000
_diffrn_orient_matrix_UB_32      -0.0746262000
_diffrn_orient_matrix_UB_33      0.0122586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            58606
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.594
_diffrn_reflns_theta_min         2.370
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       needle
_exptl_crystal_F_000             5856
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1277
_refine_ls_number_reflns         15863
_refine_ls_number_restraints     997
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0737
_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^)+(0.1208P)^2^+9.1525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9157
_reflns_number_total             15863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01061e2.cif
_cod_data_source_block           tx3975a_sq
_cod_database_code               7129896
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     C,H,O,N
_reflns_odcompleteness_completeness 99.61
_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
 C82-C81 = C80-C79 = C86-C65 = C67-C66 = C70-C71 = C68-C69 = C88-C89 = C91-C92
 1.51 with sigma of 0.01
 C126-C125 = C127-C125 = C128-C125 = C111-N4 = C112-C111 = C113-C112 = C114-
 C113 = C114-C115 = C94-C93 = C95-C94 = C96-C95 = C97-C96 = C97-C98 = C107-C109
 = C107-C108 = C107-C110 = C116-C115 = C112-C111
 1.54 with sigma of 0.01
 C121-C120 = C122-C121 = C123-C122 = C123-C124 = C117-C124 = C118-C117 = C119-
 C118 = C119-C81 = C80-C117 = C80-C81 = C82-C83 = C84-C83 = C84-C85 = C87-C85 =
 C87-C88 = C82-C88 = C86-C85 = C86-C67 = C68-C67 = C68-C92 = C87-C92 = C68-C69 =
  C99-C69 = C70-C106 = C105-C106 = C70-C69 = C99-C100 = C100-C101 = C102-C101 =
 C103-C102 = C103-C104 = C105-C104 = C72-C71 = C73-C72 = C74-C73 = C74-C90 =
 C75-C74 = C79-C78 = C80-C79 = C79-C89
 1.39 with sigma of 0.01
 N4-C111 = N3-C93
 1.46 with sigma of 0.01
 N4-C77 = N4-C76
 1.38 with sigma of 0.01
 O7-C77 = O8-C76 = O5-C65 = O6-C66
 1.22 with sigma of 0.01
 C122-C125 = C107-C102
 1.51 with sigma of 0.01
 C115-C113
 2.5 with sigma of 0.02
 C111-C113
 2.5 with sigma of 0.02
 C98-C96
 2.5 with sigma of 0.02
 C114-C112
 2.5 with sigma of 0.02
 C95-C93
 2.5 with sigma of 0.02
 C96-C94
 2.5 with sigma of 0.02
 C95-C97
 2.5 with sigma of 0.02
 N3-C94
 2.5 with sigma of 0.02
 N4-C112
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O5 \\sim O6 \\sim O7 \\sim O8 \\sim N3 \\sim N4 \\sim C65 \\sim C66 \\sim C67
\\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim C72 \\sim C73 \\sim C74 \\sim C75
\\sim C76 \\sim C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81 \\sim C82 \\sim C83
\\sim C84 \\sim C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89 \\sim C90 \\sim C91
\\sim C92 \\sim C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97 \\sim C98 \\sim C99
\\sim C100 \\sim C101 \\sim C102 \\sim C103 \\sim C104 \\sim C105 \\sim C106
\\sim C107 \\sim C108 \\sim C109 \\sim C110 \\sim C111 \\sim C112 \\sim C113
\\sim C114 \\sim C115 \\sim C116 \\sim C117 \\sim C118 \\sim C119 \\sim C120
\\sim C121 \\sim C122 \\sim C123 \\sim C124 \\sim C125 \\sim C126 \\sim C127
\\sim C128: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C98) \\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(C88) \\sim Ueq, Uanis(C79)
\\sim Ueq, Uanis(C90) \\sim Ueq, Uanis(C82) \\sim Ueq, Uanis(C87) \\sim Ueq,
Uanis(C80) \\sim Ueq, Uanis(C78) \\sim Ueq, Uanis(C91) \\sim Ueq, Uanis(C74)
\\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C85) \\sim Ueq,
Uanis(C92) \\sim Ueq, Uanis(C117) \\sim Ueq, Uanis(C75) \\sim Ueq, Uanis(C76)
\\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C119) \\sim Ueq,
Uanis(C84) \\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C118)
\\sim Ueq, Uanis(C124) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(N4) \\sim Ueq,
Uanis(C70) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C67)
\\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C120) \\sim Ueq, Uanis(C123) \\sim Ueq,
Uanis(C111) \\sim Ueq, Uanis(C106) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(N3)
\\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C99) \\sim Ueq, Uanis(C121) \\sim Ueq,
Uanis(C122) \\sim Ueq, Uanis(C112) \\sim Ueq, Uanis(C105) \\sim Ueq, Uanis(C93)
\\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(C125) \\sim Ueq,
Uanis(C113) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C94) \\sim Ueq, Uanis(C101)
\\sim Ueq, Uanis(C127) \\sim Ueq, Uanis(C126) \\sim Ueq, Uanis(C128) \\sim Ueq,
Uanis(C114) \\sim Ueq, Uanis(C103) \\sim Ueq, Uanis(C95) \\sim Ueq, Uanis(C102)
\\sim Ueq, Uanis(C115) \\sim Ueq, Uanis(C96) \\sim Ueq, Uanis(C107) \\sim Ueq,
Uanis(C97) \\sim Ueq, Uanis(C108) \\sim Ueq, Uanis(C109) \\sim Ueq, Uanis(C110)
\\sim Ueq, Uanis(C116) \\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(O7) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O5(0.5) O6(0.5) O7(0.5) O8(0.5) N3(0.5) N4(0.5) C65(0.5) C66(0.5)
 C67(0.5) C68(0.5) C69(0.5) C70(0.5) C71(0.5) C72(0.5) H72(0.5) C73(0.5)
 H73(0.5) C74(0.5) C75(0.5) C76(0.5) C77(0.5) C78(0.5) C79(0.5) C80(0.5)
 C81(0.5) C82(0.5) C83(0.5) H83(0.5) C84(0.5) H84(0.5) C85(0.5) C86(0.5)
 C87(0.5) C88(0.5) C89(0.5) C90(0.5) C91(0.5) C92(0.5) C93(0.5) H93A(0.5)
 H93B(0.5) C94(0.5) H94A(0.5) H94B(0.5) C95(0.5) H95A(0.5) H95B(0.5) C96(0.5)
 H96A(0.5) H96B(0.5) C97(0.5) H97A(0.5) H97B(0.5) C98(0.5) H98A(0.5) H98B(0.5)
 H98C(0.5) C99(0.5) C100(0.5) H100(0.5) C101(0.5) H101(0.5) C102(0.5) C103(0.5)
 H103(0.5) C104(0.5) H104(0.5) C105(0.5) C106(0.5) H106(0.5) C107(0.5)
 C108(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C109(0.5) H10D(0.5) H10E(0.5)
 H10F(0.5) C110(0.5) H11A(0.5) H11B(0.5) H11C(0.5) C111(0.5) H11D(0.5)
 H11E(0.5) C112(0.5) H11F(0.5) H11G(0.5) C113(0.5) H11H(0.5) H11I(0.5)
 C114(0.5) H11J(0.5) H11K(0.5) C115(0.5) H11L(0.5) H11M(0.5) C116(0.5)
 H11N(0.5) H11O(0.5) H11P(0.5) C117(0.5) C118(0.5) C119(0.5) H119(0.5)
 C120(0.5) H120(0.5) C121(0.5) H121(0.5) C122(0.5) C123(0.5) H123(0.5)
 C124(0.5) H124(0.5) C125(0.5) C126(0.5) H12A(0.5) H12B(0.5) H12C(0.5)
 C127(0.5) H12D(0.5) H12E(0.5) H12F(0.5) C128(0.5) H12G(0.5) H12H(0.5) H12I(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,
 H31B), C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B), C62(H62A,H62B),
 C63(H63A,H63B), C93(H93A,H93B), C94(H94A,H94B), C95(H95A,H95B), C96(H96A,H96B),
  C97(H97A,H97B), C111(H11D,H11E), C112(H11F,H11G), C113(H11H,H11I), C114(H11J,
 H11K), C115(H11L,H11M)
5.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21),
 C42(H42), C43(H43), C48(H48), C49(H49), C51(H51), C52(H52), C54(H54), C72(H72),
  C73(H73), C83(H83), C84(H84), C100(H100), C101(H101), C103(H103), C104(H104),
 C106(H106), C119(H119), C120(H120), C121(H121), C123(H123), C124(H124)
5.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C32(H32A,H32B,
 H32C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C), C64(H64A,
 H64B,H64C), C98(H98A,H98B,H98C), C108(H10A,H10B,H10C), C109(H10D,H10E,H10F),
 C110(H11A,H11B,H11C), C116(H11N,H11O,H11P), C126(H12A,H12B,H12C), C127(H12D,
 H12E,H12F), C128(H12G,H12H,H12I)
;
_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 2.308
_oxdiff_exptl_absorpt_empirical_full_min 0.553