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_7127611
_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         'C176 H220 O8'
_chemical_formula_sum            'C176 H220 O8'
_chemical_formula_weight         2463.51
_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             2020-08-19
_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                105.764(2)
_cell_angle_beta                 95.876(2)
_cell_angle_gamma                95.998(2)
_cell_formula_units_Z            2
_cell_length_a                   15.3455(4)
_cell_length_b                   18.7629(5)
_cell_length_c                   28.3210(5)
_cell_measurement_reflns_used    14768
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      72.3530
_cell_measurement_theta_min      2.8930
_cell_volume                     7731.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.953
_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    -90.00  -2.00   1.00    1.70    --  -42.06 125.00 -30.00   88
  2  \w    -69.00  31.00   1.00    1.70    --  -42.06  57.00 -90.00  100
  3  \w   -111.00 -14.00   1.00    1.70    --  -42.06 -57.00 120.00   97
  4  \w    124.00 176.00   1.00    6.79    --  104.13  61.00  30.00   52
  5  \w     33.00 126.00   1.00    6.79    --  104.13 -61.00  90.00   93
  6  \w     62.00 110.00   1.00    6.79    --  104.13 -94.00 -30.00   48
  7  \w     21.00 110.00   1.00    6.79    --  104.13 -94.00  90.00   89
  8  \w     43.00 129.00   1.00    6.79    --  104.13 -45.00 -30.00   86
  9  \w     33.00 126.00   1.00    6.79    --  104.13 -45.00-120.00   93
 10  \w     24.00 109.00   1.00    6.79    --  104.13 -94.00-120.00   85
 11  \w     18.00 178.00   1.00    6.79    --  104.13   0.00  30.00  160
;
_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      0.0108284000
_diffrn_orient_matrix_UB_12      0.0860605000
_diffrn_orient_matrix_UB_13      0.0144926000
_diffrn_orient_matrix_UB_21      0.0763948000
_diffrn_orient_matrix_UB_22      0.0004378000
_diffrn_orient_matrix_UB_23      -0.0312721000
_diffrn_orient_matrix_UB_31      -0.0665595000
_diffrn_orient_matrix_UB_32      -0.0037238000
_diffrn_orient_matrix_UB_33      -0.0454704000
_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  0.0483
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            48409
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.412
_diffrn_reflns_theta_min         2.923
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.316
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_description       block
_exptl_crystal_F_000             2680
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and MeOH  by solvent layering'
_exptl_crystal_size_max          0.633
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.207
_refine_diff_density_max         2.029
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.537
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1605
_refine_ls_number_reflns         29169
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.537
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.1307
_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          0.3528
_refine_ls_wR_factor_ref         0.3996
_reflns_Friedel_coverage         0.000
_reflns_number_gt                21002
_reflns_number_total             29169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07773a2.cif
_cod_data_source_block           20hir_cd02_2
_cod_depositor_comments
'Adding full bibliography for 7127610--7127611.cif.'
_cod_database_code               7127611
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 99.00
_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
 C1b-C146 \\sim C1b-C1f \\sim C142-C141
 with sigma of 0.02
 C1b-C1f \\sim C145-C144
 with sigma of 0.02
 C1e-C99a \\sim C1a-C99a \\sim C1c-C99a \\sim C102-C99 \\sim C100-C99 \\sim
C101-C99
 with sigma of 0.02
 C145-C146 \\sim C1b-C146
 with sigma of 0.02
 C1d-C142 \\sim C143-C142
 with sigma of 0.02
 C1d-C1f \\sim C143-C144
 with sigma of 0.02
 C97a-C98 \\sim C97a-C96a
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C185) = Uanis(C184) = Uanis(C183) = Uanis(C182) = Uanis(C181) =
Uanis(C180) = Uanis(C179) = Uanis(C178) = Uanis(C177) = Uanis(C176)
Uanis(C99) = Uanis(C99a)
Uanis(C144) = Uanis(C1f)
Uanis(C99a) = Uanis(C99)
Uanis(C96a) = Uanis(C96)
Uanis(C1c) = Uanis(C1a) = Uanis(C102) = Uanis(C1e) = Uanis(C100) = Uanis(C101)
Uanis(C95a) = Uanis(C97a) = Uanis(C95) = Uanis(C97)
Uanis(C1b) = Uanis(C145)
Uanis(C1d) = Uanis(C143)
Uanis(C142) = Uanis(C1d) = Uanis(C143) = Uanis(C1f) = Uanis(C144)
4. Others
 Sof(H14E)=Sof(H14F)=Sof(C143)=Sof(H14I)=Sof(H14J)=Sof(C144)=Sof(H14K)=
 Sof(H14L)=Sof(C145)=Sof(H14M)=Sof(H14N)=Sof(H14O)=Sof(H14P)=Sof(H14Q)=1-FVAR(1)
 Sof(H14G)=Sof(H14H)=Sof(H14R)=Sof(H14S)=Sof(H14T)=Sof(C1b)=Sof(H14U)=
 Sof(H14V)=Sof(C1d)=Sof(H17H)=Sof(H17I)=Sof(C1f)=Sof(H18N)=Sof(H18O)=FVAR(1)
 Sof(H94)=Sof(C95)=Sof(H95)=Sof(C96)=Sof(C97)=Sof(H97)=Sof(H98)=Sof(C99)=
 Sof(C100)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C101)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C102)=Sof(H10G)=Sof(H10H)=Sof(H10I)=1-FVAR(2)
 Sof(H94A)=Sof(H98A)=Sof(C96a)=Sof(C1a)=Sof(H13J)=Sof(H13K)=Sof(H13L)=
 Sof(C99a)=Sof(C97a)=Sof(H149)=Sof(C95a)=Sof(H161)=Sof(C1c)=Sof(H16A)=Sof(H16B)=
 Sof(H16C)=Sof(C1e)=Sof(H17J)=Sof(H17K)=Sof(H17L)=FVAR(2)
5.a Riding coordinates:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C44(H44A,H44B,
 H44C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C54(H54A,H54B,H54C), C55(H55A,
 H55B,H55C), C56(H56A,H56B,H56C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C),
 C66(H66A,H66B,H66C), C74(H74A,H74B,H74C), C75(H75A,H75B,H75C), C76(H76A,H76B,
 H76C), C90(H90A,H90B,H90C), C91(H91A,H91B,H91C), C92(H92A,H92B,H92C),
 C100(H10A,H10B,H10C), C101(H10D,H10E,H10F), C102(H10G,H10H,H10I), C109(H10J,
 H10K,H10L), C110(H11A,H11B,H11C), C111(H11D,H11E,H11F), C120(H12A,H12B,H12C),
 C121(H12D,H12E,H12F), C122(H12G,H12H,H12I), C130(H13A,H13B,H13C), C131(H13D,
 H13E,H13F), C132(H13G,H13H,H13I), C1a(H13J,H13K,H13L), C146(H14R,H14S,H14T),
 C146(H14O,H14P,H14Q), C159(H15S,H15T,H15U), C1c(H16A,H16B,H16C), C172(H17E,
 H17F,H17G), C1e(H17J,H17K,H17L), C185(H18K,H18L,H18M)
5.b Secondary CH2 refined with riding coordinates:
 C136(H13M,H13N), C138(H13O,H13P), C139(H13Q,H13R), C140(H14A,H14B), C141(H14C,
 H14D), C142(H14E,H14F), C142(H14G,H14H), C143(H14I,H14J), C144(H14K,H14L),
 C145(H14M,H14N), C1b(H14U,H14V), C150(H15A,H15B), C151(H15C,H15D), C152(H15E,
 H15F), C153(H15G,H15H), C154(H15I,H15J), C155(H15K,H15L), C156(H15M,H15N),
 C157(H15O,H15P), C158(H15Q,H15R), C163(H16D,H16E), C164(H16F,H16G), C165(H16H,
 H16I), C166(H16J,H16K), C167(H16L,H16M), C168(H16N,H16O), C169(H16P,H16Q),
 C170(H17A,H17B), C171(H17C,H17D), C1d(H17H,H17I), C176(H17M,H17N), C177(H17O,
 H17P), C178(H17Q,H17R), C179(H17S,H17T), C180(H18A,H18B), C181(H18C,H18D),
 C182(H18E,H18F), C183(H18G,H18H), C184(H18I,H18J), C1f(H18N,H18O)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7), C15(H15), C19(H19), C28(H28), C29(H29),
 C31(H31), C32(H32), C38(H38), C39(H39), C41(H41), C42(H42), C48(H48), C49(H49),
  C51(H51), C52(H52), C58(H58), C59(H59), C61(H61), C62(H62), C68(H68),
 C69(H69), C71(H71), C72(H72), C84(H84), C85(H85), C87(H87), C88(H88), C94(H94),
  C94(H94A), C95(H95), C97(H97), C98(H98A), C98(H98), C104(H104), C105(H105),
 C107(H107), C108(H108), C114(H114), C115(H115), C117(H117), C118(H118),
 C124(H124), C125(H125), C127(H127), C128(H128), C97a(H149), C95a(H161)
;
_olex2_date_sample_data_collection 2020-07-16
_olex2_diffrn_ambient_temperature_device 'Cryojet - Oxford Instruments'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id CD_182
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.694
_oxdiff_exptl_absorpt_empirical_full_min 0.731