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_7129895
_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         'C37.97 H32.53 N4 O4'
_chemical_formula_sum            'C37.97 H32.53 N4 O4'
_chemical_formula_weight         608.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-04 deposited with the CCDC.	2022-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.811(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.4426(10)
_cell_length_b                   17.7385(5)
_cell_length_c                   7.0866(2)
_cell_measurement_reflns_used    6194
_cell_measurement_temperature    169.99(15)
_cell_measurement_theta_max      75.0020
_cell_measurement_theta_min      3.0480
_cell_volume                     3068.88(18)
_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(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.952
_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    -22.00  28.00   0.50    4.00    --  -47.45  19.00   0.00  100
  2  \w    -16.00  24.00   0.50    4.00    --  -47.45  96.00  -7.00   80
  3  \w    -22.00  24.00   0.50    4.00    --  -47.45  19.00  90.00   92
  4  \w    -20.00  25.00   0.50    4.00    --  -47.45  38.00 120.00   90
  5  \w    -26.00  28.00   0.50    4.00    --   47.45 -19.00 150.00  108
  6  \w     57.00 101.00   0.50   13.00    --  103.25 -94.00  90.00   88
  7  \w     45.00  70.00   0.50   13.00    --  103.25 -61.00 150.00   50
  8  \w     32.00  65.00   0.50   13.00    --  103.25 -61.00  90.00   66
  9  \w     32.00 100.00   0.50   13.00    --  103.25 -94.00  30.00  136
 10  \w     31.00  60.00   0.50   13.00    --  103.25 -61.00  30.00   58
 11  \w    -15.00  29.00   0.50    4.00    --   47.45 -96.00-116.00   88
 12  \w     44.00  69.00   0.50   13.00    --  103.25 -96.00-116.00   50
 13  \w     44.00 109.00   0.50   13.00    --  103.25 -77.00-120.00  130
 14  \w     34.00  68.00   0.50   13.00    --  103.25 -61.00-120.00   68
 15  \w     94.00 167.00   0.50   13.00    --  103.25  61.00 -60.00  146
 16  \w     93.00 154.00   0.50   13.00    --  103.25  96.00  -7.00  122
 17  \w    119.00 152.00   0.50   13.00    --  103.25  61.00  90.00   66
 18  \w     91.00 149.00   0.50   13.00    --  103.25  45.00  90.00  116
 19  \w    -57.00 -30.00   0.50   13.00    --  -99.00  61.00-180.00   54
 20  \w    -66.00 -31.00   0.50   13.00    --  -99.00  61.00-150.00   70
 21  \w    -66.00 -27.00   0.50   13.00    --  -99.00  61.00 -90.00   78
 22  \w    -78.00 -20.00   0.50    4.00    --  -47.45  96.00  -7.00  116
 23  \w    -67.00 -39.00   0.50   13.00    --  -99.00  61.00   0.00   56
 24  \w    -81.00 -40.00   0.50   13.00    --  -99.00  96.00  -7.00   82
 25  \w   -110.00 -83.00   0.50   13.00    --  -99.00 125.00   0.00   54
 26  \w   -151.00-126.00   0.50   13.00    --  -99.00 -96.00-116.00   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      -0.0275565000
_diffrn_orient_matrix_UB_12      -0.0676767000
_diffrn_orient_matrix_UB_13      0.0931646000
_diffrn_orient_matrix_UB_21      0.0523963000
_diffrn_orient_matrix_UB_22      -0.0470532000
_diffrn_orient_matrix_UB_23      -0.0196430000
_diffrn_orient_matrix_UB_31      0.0218248000
_diffrn_orient_matrix_UB_32      0.0273869000
_diffrn_orient_matrix_UB_33      0.1957287000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            21056
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.634
_diffrn_reflns_theta_min         3.079
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51780
_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            'fluorescent intense red'
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       needle
_exptl_crystal_F_000             1281
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6065
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0998P)^2^+0.5457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4433
_reflns_number_total             6065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01061e2.cif
_cod_data_source_block           tx5648
_cod_database_code               7129895
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'C, H, O,N'
_reflns_odcompleteness_completeness 99.49
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C36A-C35 = C36-C35 = C37A-C36A = C38-C37A
 1.54 with sigma of 0.01
 C35A-C34 = C35-C34 = C36A-C35A = C36-C35 = C37-C36 = C37A-C36A = C38-C37A =
 C38-C37 = C34-C33
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37A) \\sim Ueq, Uanis(C37)
\\sim Ueq, Uanis(C36A) \\sim Ueq, Uanis(C38) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.01
Uanis(C35A) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C36A) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37A) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C37) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.01
4. Others
 Sof(H38D)=Sof(H38E)=Sof(H38F)=Sof(C36A)=Sof(H36C)=Sof(H36D)=Sof(C37A)=
 Sof(H37C)=Sof(H37D)=1-FVAR(1)
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H38A)=Sof(H38B)=
 Sof(H38C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,
 H31B), C33(H33A,H33B), C34(H34A,H34B), C34(H34C,H34D), C35(H35A,H35B),
 C36(H36A,H36B), C37(H37A,H37B), C36A(H36C,H36D), C37A(H37C,H37D), C35A(H35C,
 H35D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C12(H12), C19(H19), C20(H20)
5.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C38(H38A,H38B,H38C), C38(H38D,H38E,H38F)
;
_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 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.533