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_7129894
_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         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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     iterative
_audit_creation_date             2021-04-01
_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                95.710(7)
_cell_angle_beta                 103.580(6)
_cell_angle_gamma                93.738(6)
_cell_formula_units_Z            4
_cell_length_a                   10.8776(7)
_cell_length_b                   14.0655(13)
_cell_length_c                   18.9337(13)
_cell_measurement_reflns_used    4305
_cell_measurement_temperature    169.99(14)
_cell_measurement_theta_max      73.5960
_cell_measurement_theta_min      2.3670
_cell_volume                     2790.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.933
_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    -56.00  26.00   0.50    5.00    --  -46.32  57.00 -30.00  164
  2  \w     24.00 118.00   0.50    5.00    --   46.32  77.00 -90.00  188
  3  \w     85.00 127.00   0.50   20.00    --  103.25 110.00 -99.00   84
  4  \w     93.00 167.00   0.50   20.00    --  103.25  45.00  60.00  148
  5  \w    110.00 168.00   0.50   20.00    --  103.25  30.00  90.00  116
  6  \w     47.00  82.00   0.50   20.00    --  103.25 -94.00  90.00   70
  7  \w     83.00 109.00   0.50   20.00    --  103.25-125.00  30.00   52
  8  \w     33.00 110.00   0.50   20.00    --  103.25-110.00 165.00  154
  9  \w     32.00  64.00   0.50   20.00    --  103.25-125.00  30.00   64
 10  \w     31.00 126.00   0.50   20.00    --  103.25 -77.00 -30.00  190
 11  \w     34.00 108.00   0.50   20.00    --  103.25 -94.00-120.00  148
 12  \w     37.00 105.00   0.50   20.00    --  103.25 -45.00 -60.00  136
 13  \w      5.00  84.00   0.50    5.00    --   46.32-110.00 165.00  158
 14  \w    -24.00  59.00   0.50    5.00    --   46.32 -57.00 150.00  166
 15  \w    -86.00   1.00   0.50    5.00    --  -46.32 110.00 -99.00  174
 16  \w    -79.00 -29.00   0.50   20.00    --  -99.00 125.00  60.00  100
 17  \w    -94.00 -51.00   0.50   20.00    --  -99.00 110.00 -99.00   86
 18  \w    -88.00 -61.00   0.50   20.00    --  -99.00  30.00 -90.00   54
 19  \w   -118.00 -28.00   0.50   20.00    --  -99.00  77.00 -90.00  180
 20  \w   -115.00 -80.00   0.50   20.00    --  -99.00 125.00  60.00   70
 21  \w   -167.00 -86.00   0.50   20.00    --  -99.00 -30.00-180.00  162
 22  \w   -115.00 -75.00   0.50    5.00    --  -46.32-125.00 -60.00   80
 23  \w   -112.00 -83.00   0.50    5.00    --  -46.32-125.00-150.00   58
 24  \w   -137.00 -98.00   0.50   20.00    --  -99.00 -30.00   0.00   78
 25  \w   -162.00 -97.00   0.50   20.00    --  -99.00 -45.00-120.00  130
 26  \w   -137.00-110.00   0.50   20.00    --  -99.00-110.00 165.00   54
 27  \w   -168.00-111.50   0.50   20.00    --  -99.00 -45.00 150.00  113
;
_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      -0.0794336000
_diffrn_orient_matrix_UB_12      -0.0904817000
_diffrn_orient_matrix_UB_13      0.0094759000
_diffrn_orient_matrix_UB_21      0.0519457000
_diffrn_orient_matrix_UB_22      -0.0588738000
_diffrn_orient_matrix_UB_23      -0.0577917000
_diffrn_orient_matrix_UB_31      0.1113547000
_diffrn_orient_matrix_UB_32      -0.0237835000
_diffrn_orient_matrix_UB_33      0.0606349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29717
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.871
_diffrn_reflns_theta_min         2.418
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.261
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     846
_refine_ls_number_reflns         10852
_refine_ls_number_restraints     335
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1966
_refine_ls_R_factor_gt           0.1411
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3237
_refine_ls_wR_factor_ref         0.3799
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5240
_reflns_number_total             10852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01061e2.cif
_cod_data_source_block           tx1154
_cod_database_code               7129894
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_reflns_odcompleteness_completeness 98.82
_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
 C71A-C70A = C71A-C72A
 1.54 with sigma of 0.01
 C51-C50 = C50-C49 = C52-C51 = C53-C52 = C54-C53
 1.54 with sigma of 0.01
 C50-C49 = C50A-C49 = C51A-C50A = C51-C50 = C52-C51 = C52A-C51A = C53A-C52A =
 C53-C52 = C54-C53 = C54A-C53A
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C69 \\sim C70 \\sim C71 \\sim C72 \\sim C69A \\sim C70A \\sim C71A \\sim C72A
\\sim C68: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C50A \\sim C51A \\sim C52A
\\sim C53A \\sim C54A: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
Uanis(C69) \\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C72)
\\sim Ueq, Uanis(C69A) \\sim Ueq, Uanis(C70A) \\sim Ueq, Uanis(C71A) \\sim Ueq,
Uanis(C72A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C50) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53)
\\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C50A) \\sim Ueq, Uanis(C51A) \\sim Ueq,
Uanis(C52A) \\sim Ueq, Uanis(C53A) \\sim Ueq, Uanis(C54A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H68C)=Sof(H68D)=Sof(C69A)=Sof(H69C)=Sof(H69D)=Sof(C70A)=Sof(H70C)=
 Sof(H70D)=Sof(C71A)=Sof(H71C)=Sof(H71D)=Sof(C72A)=Sof(H72D)=Sof(H72E)=
 Sof(H72F)=1-FVAR(1)
 Sof(H68A)=Sof(H68B)=Sof(C69)=Sof(H69A)=Sof(H69B)=Sof(C70)=Sof(H70A)=Sof(H70B)=
 Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(H72C)=FVAR(1)
 Sof(H49C)=Sof(H49D)=Sof(C50A)=Sof(H50C)=Sof(H50D)=Sof(C51A)=Sof(H51C)=
 Sof(H51D)=Sof(C52A)=Sof(H52C)=Sof(H52D)=Sof(C53A)=Sof(H53C)=Sof(H53D)=
 Sof(C54A)=Sof(H54D)=Sof(H54E)=Sof(H54F)=1-FVAR(2)
 Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C51)=Sof(H51A)=Sof(H51B)=
 Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(C54)=Sof(H54A)=
 Sof(H54B)=Sof(H54C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,
 H29B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C49(H49A,H49B), C49(H49C,H49D), C50(H50A,H50B), C51(H51A,H51B),
  C52(H52A,H52B), C53(H53A,H53B), C67(H67A,H67B), C68(H68A,H68B), C68(H68C,
 H68D), C69(H69A,H69B), C70(H70A,H70B), C71(H71A,H71B), C69A(H69C,H69D),
 C70A(H70C,H70D), C71A(H71C,H71D), C50A(H50C,H50D), C51A(H51C,H51D), C52A(H52C,
 H52D), C53A(H53C,H53D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C14(H14), C17(H17), C18(H18), C19(H19),
 C40(H40), C41(H41), C42(H42), C46(H46), C58(H58), C59(H59), C60(H60), C64(H64)
5.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C36(H36A,H36B,H36C), C54(H54A,H54B,H54C), C72(H72A,H72B,
 H72C), C72A(H72D,H72E,H72F), C54A(H54D,H54E,H54F)
;
_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 4.742
_oxdiff_exptl_absorpt_empirical_full_min 0.349