Synthesis and crystal packing of perylene-derivatives with extreme sterically demanding pentaphenylbenzene bay-substituents.
Dusold, Carolin; Weiss, Corinna; Hampel, Frank; Hirsch, Andreas; Chemical communications (Cambridge, England) 57 (2021) 583–586; doi:10.1039/d0cc07773a

data_7127610
_publ_section_title
;
 Synthesis and crystal packing of perylene-derivatives with extreme
 sterically demanding pentaphenylbenzene bay-substituents.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              583
_journal_page_last               586
_journal_paper_doi               10.1039/d0cc07773a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C88 H116 O8'
_chemical_formula_sum            'C88 H116 O8'
_chemical_formula_weight         1301.80
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-11-26 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                84.401(2)
_cell_angle_beta                 66.537(2)
_cell_angle_gamma                69.279(2)
_cell_formula_units_Z            2
_cell_length_a                   16.5010(4)
_cell_length_b                   16.5277(4)
_cell_length_c                   16.5470(3)
_cell_measurement_reflns_used    25917
_cell_measurement_temperature    113(14)
_cell_measurement_theta_max      68.8990
_cell_measurement_theta_min      2.8940
_cell_volume                     3866.92(17)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      113(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_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     -9.00  16.00   1.00   15.28    --   34.00 102.00  -4.71   25
  2  \w      5.00  30.00   1.00   15.28    --   42.00  89.00-122.23   25
  3  \w    -91.00  -2.00   1.00   15.28    --  -42.18 125.00  90.00   89
  4  \w   -115.00 -61.00   1.00   15.28    --  -42.18 -57.00 -30.00   54
  5  \w   -116.00 -18.00   1.00   15.28    --  -42.18 -38.00  90.00   98
  6  \w   -115.00 -14.00   1.00   15.28    --  -42.18 -57.00-150.00  101
  7  \w   -100.00 -21.00   1.00   15.28    --  -42.18 -38.00   0.00   79
  8  \w    -56.00 -14.00   1.00   15.28    --  -42.18 -57.00 -30.00   42
  9  \w      2.00  82.00   1.00   15.28    --   42.18 -99.00 -30.00   80
 10  \w     16.00  41.00   1.00   15.28    --   50.00  82.00  53.63   25
 11  \w     16.00  42.00   1.00   15.28    --   50.00  82.00 -16.12   26
 12  \w     17.00  42.00   1.00   15.28    --   50.00  82.00-164.88   25
 13  \w     16.00  43.00   1.00   15.28    --   50.00  82.00 -85.09   27
 14  \w     16.00  41.00   1.00   15.28    --   50.00  81.00 130.93   25
 15  \w     89.00 130.00   1.00   15.28    --   62.00  77.00-143.58   41
 16  \w     29.00  55.00   1.00   15.28    --   62.00  77.00-143.58   26
 17  \w     30.00  56.00   1.00   15.28    --   62.00  77.00  74.99   26
 18  \w     30.00  58.00   1.00   15.28    --   62.00  77.00 156.88   28
 19  \w     34.00  59.00   1.00   15.28    --   66.00  77.00-103.82   25
 20  \w     33.00  69.00   1.00   15.28    --   66.00  77.00 -75.75   36
 21  \w     33.00  59.00   1.00   15.28    --   66.00  77.00 -13.72   26
 22  \w     38.00  69.00   1.00   15.28    --   70.00  76.00   4.35   31
 23  \w     38.00  64.00   1.00   15.28    --   70.00  76.00  80.28   26
 24  \w     38.00  64.00   1.00   15.28    --   70.00  76.00 101.80   26
 25  \w    117.00 146.00   1.00   15.28    --   70.00  76.00   4.35   29
 26  \w     42.00  75.00   1.00   61.09    --   74.00  77.00 151.72   33
 27  \w     43.00  77.00   1.00   61.09    --   74.00  76.00 -60.67   34
 28  \w     47.00  74.00   1.00   61.09    --   78.00  69.00 121.83   27
 29  \w     46.00  72.00   1.00   61.09    --   78.00  76.00-173.88   26
 30  \w     46.00  76.00   1.00   61.09    --   78.00  73.00  24.46   30
 31  \w     50.00  76.00   1.00   61.09    --   82.00  73.00-141.63   26
 32  \w     50.00  77.00   1.00   61.09    --   82.00  74.00 -38.61   27
 33  \w     54.00  80.00   1.00   61.09    --   86.00  76.00-110.91   26
 34  \w     54.00  83.00   1.00   61.09    --   86.00  75.00  59.10   29
 35  \w     60.00  85.00   1.00   61.09    --   90.00  69.00 130.19   25
 36  \w     67.00 144.00   1.00   61.09    --   98.29  77.00 -60.00   77
 37  \w     35.00 117.00   1.00   61.09    --   98.29-125.00-150.00   82
 38  \w     24.00  80.00   1.00   61.09    --   98.29 -94.00 120.00   56
 39  \w     66.00 157.00   1.00   61.09    --   98.29  77.00  60.00   91
 40  \w     66.00  92.00   1.00   61.09    --   98.29  77.00 120.00   26
 41  \w     95.00 174.00   1.00   61.09    --   98.29  77.00 -90.00   79
 42  \w     68.00 158.00   1.00   61.09    --   98.29  77.00  90.00   90
 43  \w     36.00 109.00   1.00   61.09    --   98.29 -94.00 -30.00   73
 44  \w     66.00 148.00   1.00   61.09    --   98.29  77.00-180.00   82
 45  \w     66.00 158.00   1.00   61.09    --   98.29  77.00  30.00   92
 46  \w     66.00 145.00   1.00   61.09    --   98.29  77.00-120.00   79
 47  \w     23.00 102.00   1.00   61.09    --   98.29 -94.00  60.00   79
 48  \w     67.00 162.00   1.00   61.09    --   98.29  77.00 150.00   95
 49  \w     22.00 109.00   1.00   61.09    --   98.29 -94.00-120.00   87
 50  \w     67.00  93.00   1.00   61.09    --   98.29  77.00 -90.00   26
 51  \w     66.00 143.00   1.00   61.09    --   98.29  77.00   0.00   77
 52  \w     68.00  97.00   1.00   61.09    --   98.29  69.00 143.72   29
 53  \w    103.00 173.00   1.00   61.09    --   98.29  77.00 120.00   70
 54  \w     66.00 170.00   1.00   61.09    --   98.29  77.00-150.00  104
 55  \w    106.00 131.00   1.00   61.09    --   98.29 -77.00 -90.00   25
 56  \w     26.00  64.00   1.00   61.09    --   98.29 -77.00 -90.00   38
 57  \w     66.00 174.00   1.00   61.09    --   98.29  77.00 -30.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1078174000
_diffrn_orient_matrix_UB_12      0.0318819000
_diffrn_orient_matrix_UB_13      0.0300595000
_diffrn_orient_matrix_UB_21      -0.0058720000
_diffrn_orient_matrix_UB_22      -0.0654016000
_diffrn_orient_matrix_UB_23      0.0732920000
_diffrn_orient_matrix_UB_31      -0.0099525000
_diffrn_orient_matrix_UB_32      0.0682870000
_diffrn_orient_matrix_UB_33      0.0636564000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            69673
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.660
_diffrn_reflns_theta_min         2.862
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description       needle
_exptl_crystal_F_000             1416
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of toluene and methanol  by solvent layering'
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.081
_refine_diff_density_max         2.964
_refine_diff_density_min         -1.582
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.789
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     700
_refine_ls_number_reflns         14290
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      2.813
_refine_ls_R_factor_all          0.2198
_refine_ls_R_factor_gt           0.1977
_refine_ls_shift/su_max          0.002
_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          0.5463
_refine_ls_wR_factor_ref         0.5795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11376
_reflns_number_total             14290
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07773a2.cif
_cod_data_source_block           20hir_cw02_2
_cod_depositor_comments
'Adding full bibliography for 7127610--7127611.cif.'
_cod_database_code               7127610
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C88 H116O8'
_chemical_oxdiff_usercomment     CW-185-
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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
 C101-C100 \\sim C101-C102 \\sim C103-C102 \\sim C104-C103 \\sim C104-C105
\\sim C105-C106 \\sim C106-
 C107
 with sigma of 0.02
 C91-C92 \\sim C93-C92A
 with sigma of 0.02
 C10B-C105 \\sim C10B-C103 \\sim C104-C103 \\sim C105-C104 \\sim C103-C102
\\sim C102-C101 \\sim C10A-
 C101 \\sim C10A-C103
 with sigma of 0.02
 C91-C90 \\sim C90A-C91 \\sim C89-C90A \\sim C89-C90
 with sigma of 0.02
 C66A-C65 \\sim C66-C65 \\sim C68-C67 \\sim C67-C66 \\sim C69-C68 \\sim
C69A-C68A \\sim C67A-C68A ~
 C66A-C67A \\sim C65-C64 \\sim C64-C63 \\sim C63-C62 \\sim C62-C61 \\sim C59-C61
 with sigma of 0.02
 C87-C88 \\sim C89-C90 \\sim C89-C90A \\sim C90A-C91 \\sim C91-C90
 with sigma of 0.02
 C87-C88 \\sim C87A-C88 \\sim C87A-C86 \\sim C87-C86
 with sigma of 0.02
 C87A-C88 \\sim C87-C88 \\sim C87-C86 \\sim C87A-C86
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C99) = Uanis(C100) = Uanis(C102) = Uanis(C103) = Uanis(C106) =
Uanis(C101) = Uanis(C105) = Uanis(C104) = Uanis(C107) = Uanis(C108) =
Uanis(C10C) = Uanis(C10B) = Uanis(C10A)
Uanis(C86) = Uanis(C88) = Uanis(C89) = Uanis(C87A) = Uanis(C91) = Uanis(C92) =
Uanis(C93) = Uanis(C95) = Uanis(C94) = Uanis(C90)
Uanis(C90) = Uanis(C90A)
Uanis(C73) = Uanis(C79) = Uanis(C74) = Uanis(C80) = Uanis(C78) = Uanis(C77) =
Uanis(C81) = Uanis(C76) = Uanis(C75) = Uanis(C82)
Uanis(C61) = Uanis(C62) = Uanis(C59) = Uanis(C63) = Uanis(C65) = Uanis(C66) =
Uanis(C68) = Uanis(C67) = Uanis(C69) = Uanis(C68A) = Uanis(C66A) = Uanis(C67A)
= Uanis(C69A) = Uanis(C64)
Uanis(C73) = Uanis(C74) = Uanis(C75) = Uanis(C76) = Uanis(C77) = Uanis(C78) =
Uanis(C79) = Uanis(C80) = Uanis(C81) = Uanis(C82)
Uanis(C87A) = Uanis(C87)
4. Others
 Sof(H10U)=Sof(H10V)=Sof(C107)=Sof(H10W)=Sof(H10X)=Sof(HB)=Sof(HC)=Sof(HD)=1-
 FVAR(1)
 Sof(H10S)=Sof(H10T)=Sof(H)=Sof(H10Y)=Sof(HA)=Sof(C10C)=Sof(H10Z)=Sof(HE)=
 FVAR(1)
 Sof(H65C)=Sof(H65D)=Sof(C66A)=Sof(H66C)=Sof(H66D)=Sof(C67A)=Sof(H67C)=
 Sof(H67D)=Sof(C68A)=Sof(H68C)=Sof(H68D)=Sof(C69A)=Sof(H69D)=Sof(H69E)=
 Sof(H69F)=1-FVAR(2)
 Sof(H65A)=Sof(H65B)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(C67)=Sof(H67A)=Sof(H67B)=
 Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(C69)=Sof(H69A)=Sof(H69B)=Sof(H69C)=FVAR(2)
 Sof(H86C)=Sof(H86D)=Sof(C87)=Sof(H87A)=Sof(H87B)=Sof(H88C)=Sof(H88D)=1-FVAR(3)
 Sof(H86A)=Sof(H86B)=Sof(H88A)=Sof(H88B)=Sof(C87A)=Sof(H87C)=Sof(H87D)=FVAR(3)
 Sof(H89C)=Sof(H89D)=Sof(H91C)=Sof(H91D)=Sof(H93C)=Sof(H93D)=Sof(C90A)=
 Sof(H90C)=Sof(H90D)=Sof(C92A)=Sof(H92C)=Sof(H92D)=1-FVAR(4)
 Sof(H89A)=Sof(H89B)=Sof(C90)=Sof(H90A)=Sof(H90B)=Sof(H91A)=Sof(H91B)=Sof(C92)=
 Sof(H92A)=Sof(H92B)=Sof(H93A)=Sof(H93B)=FVAR(4)
 Sof(H10E)=Sof(H10F)=Sof(H10L)=Sof(H10K)=Sof(H10R)=Sof(H10Q)=Sof(C10A)=Sof(H1)=
 Sof(HG)=Sof(C10B)=Sof(H10)=Sof(HF)=1-FVAR(5)
 Sof(H10C)=Sof(H10D)=Sof(C102)=Sof(H10G)=Sof(H10H)=Sof(H10J)=Sof(H10I)=
 Sof(C104)=Sof(H10M)=Sof(H10N)=Sof(H10P)=Sof(H10O)=FVAR(5)
5.a Riding coordinates:
 C108(H,H10Y,HA), C108(HB,HC,HD)
5.b Secondary CH2 refined with riding coordinates:
 C59(H59A,H59B), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,
 H64B), C65(H65A,H65B), C65(H65C,H65D), C66(H66A,H66B), C67(H67A,H67B),
 C68(H68A,H68B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B), C76(H76A,H76B),
  C77(H77A,H77B), C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B), C81(H81A,
 H81B), C86(H86A,H86B), C86(H86C,H86D), C87(H87A,H87B), C88(H88A,H88B),
 C88(H88C,H88D), C89(H89A,H89B), C89(H89C,H89D), C90(H90A,H90B), C91(H91A,H91B),
  C91(H91C,H91D), C92(H92A,H92B), C93(H93A,H93B), C93(H93C,H93D), C94(H94A,
 H94B), C99(H99A,H99B), C100(H10A,H10B), C101(H10C,H10D), C101(H10E,H10F),
 C102(H10G,H10H), C103(H10J,H10I), C103(H10L,H10K), C104(H10M,H10N), C105(H10P,
 H10O), C105(H10R,H10Q), C106(H10U,H10V), C106(H10S,H10T), C107(H10W,H10X),
 C66A(H66C,H66D), C67A(H67C,H67D), C68A(H68C,H68D), C87A(H87C,H87D), C90A(H90C,
 H90D), C92A(H92C,H92D), C10A(H1,HG), C10B(H10,HF), C10C(H10Z,HE)
5.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C16(H16), C18(H18), C23(H23), C24(H24), C30(H30), C35(H35),
 C36(H36), C38(H38), C39(H39), C47(H47), C48(H48), C50(H50), C51(H51)
5.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C53(H53A,H53B,
 H53C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C69(H69A,H69B,H69C), C82(H82A,
 H82B,H82C), C95(H95A,H95B,H95C), C69A(H69D,H69E,H69F)
;
_olex2_date_sample_data_collection 2020-10-23
_olex2_diffrn_ambient_temperature_device 'Cryojet - Oxford Instruments'
_olex2_exptl_crystal_mounting_method 'The crystal was mounted on a mylar loop'
_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 1.371
_oxdiff_exptl_absorpt_empirical_full_min 0.714