Perylene Diimide-Embedded Double [8]Helicenes.
Liu, Bo; Böckmann, Marcus; Jiang, Wei; Doltsinis, Nikos L.; Wang, Zhaohui; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c00954

data_4134595
_publ_section_title
;
 Perylene Diimide-Embedded Double [8]Helicenes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c00954
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '4(C H Cl3), C98 H78 N2 O4'
_chemical_formula_sum            'C102 H82 Cl12 N2 O4'
_chemical_formula_weight         1825.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.878(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.2129(4)
_cell_length_b                   14.7868(4)
_cell_length_c                   20.7684(7)
_cell_measurement_reflns_used    25243
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      74.3120
_cell_measurement_theta_min      2.9940
_cell_volume                     4535.5(2)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.955
_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     16.00  41.00   0.50    2.00    --   46.95 -21.00 152.00   50
  2  \w     67.00 102.00   0.50    4.00    --  103.25 -21.00 152.00   70
  3  \w     33.00  60.00   0.50    4.00    --  103.25 -21.00 152.00   54
  4  \w     31.00 126.00   0.50    4.00    --  103.25 -77.00 120.00  190
  5  \w     54.00  79.00   0.50    2.00    --   46.95  21.00 -41.00   50
  6  \w     44.00  75.00   0.50    2.00    --   46.95  38.00  30.00   62
  7  \w     92.00 120.00   0.50    4.00    --  103.25  21.00 -41.00   56
  8  \w    123.00 168.00   0.50    4.00    --  103.25  21.00 -41.00   90
  9  \w     91.00 169.00   0.50    4.00    --  103.25  30.00-120.00  156
 10  \w     82.00 107.00   0.50    4.00    --  103.25 -94.00 -60.00   50
 11  \w     52.00 114.00   0.50    4.00    --  103.25 -45.00 -30.00  124
 12  \w     40.00  65.00   0.50    2.00    --   46.95  57.00 120.00   50
 13  \w     24.00 109.00   0.50    2.00    --   46.95  77.00  60.00  170
 14  \w     24.00 117.00   0.50    2.00    --   46.95  77.00   0.00  186
 15  \w     31.00 107.00   0.50    4.00    --  103.25 -94.00 120.00  152
 16  \w     18.00  94.00   0.50    2.00    --   46.95-125.00 -30.00  152
 17  \w    -22.00   4.00   0.50    2.00    --   46.95 -21.00 152.00   52
 18  \w    -26.00  34.00   0.50    2.00    --   46.95 -38.00  60.00  120
 19  \w    -22.00   5.00   0.50    2.00    --  -46.95  21.00 -41.00   54
 20  \w    -68.00 -38.00   0.50    2.00    --  -46.95 -19.00  60.00   60
 21  \w    -91.00 -66.00   0.50    4.00    --  -99.00  21.00 -41.00   50
 22  \w   -120.00 -73.00   0.50    2.00    --  -46.95 -19.00  60.00   94
 23  \w    -97.00 -33.00   0.50    2.00    --  -46.95 -57.00  30.00  128
 24  \w   -103.00 -76.00   0.50    4.00    --  -99.00 -77.00  37.28   54
 25  \w   -100.00 -74.00   0.50    4.00    --  -99.00 -81.00  91.56   52
 26  \w   -104.00 -77.00   0.50    4.00    --  -99.00 -74.00  73.23   54
 27  \w   -102.00 -76.00   0.50    4.00    --  -99.00 -77.00  30.00   52
 28  \w   -100.00 -75.00   0.50    4.00    --  -99.00 -80.00  55.29   50
 29  \w   -100.00 -74.00   0.50    4.00    --  -99.00 -81.00  25.13   52
 30  \w   -104.00 -78.00   0.50    4.00    --  -99.00 -73.00  38.55   52
 31  \w   -108.00 -81.00   0.50    4.00    --  -99.00 -66.00  59.50   54
 32  \w    -99.00 -73.00   0.50    4.00    --  -99.00 -83.00  69.95   52
 33  \w   -104.00 -78.00   0.50    4.00    --  -99.00 -73.00  89.23   52
 34  \w   -100.00 -74.00   0.50    4.00    --  -99.00 -82.00 139.06   52
 35  \w   -102.00 -76.00   0.50    4.00    --  -99.00 -76.00 101.83   52
 36  \w   -102.00 -75.00   0.50    4.00    --  -99.00 -80.00  86.70   54
 37  \w   -102.00 -76.00   0.50    4.00    --  -99.00 -76.00  99.43   52
 38  \w   -100.00 -73.00   0.50    4.00    --  -99.00 -83.00 124.61   54
 39  \w   -103.00 -77.00   0.50    4.00    --  -99.00 -74.00 141.07   52
 40  \w   -108.00 -82.00   0.50    4.00    --  -99.00 -61.00 120.00   52
 41  \w   -100.00 -74.00   0.50    4.00    --  -99.00 -81.00 119.38   52
 42  \w   -102.00 -76.00   0.50    4.00    --  -99.00 -77.00  58.47   52
 43  \w   -105.00 -78.00   0.50    4.00    --  -99.00 -73.00 105.01   54
 44  \w   -102.00 -76.00   0.50    4.00    --  -99.00 -77.00 120.00   52
 45  \w   -102.00 -75.00   0.50    4.00    --  -99.00 -80.00 126.58   54
 46  \w   -102.00 -75.00   0.50    4.00    --  -99.00 -80.00 133.75   54
 47  \w   -101.00 -76.00   0.50    4.00    --  -99.00 -76.00 153.67   50
 48  \w   -106.00 -80.00   0.50    4.00    --  -99.00 -67.00 122.74   52
 49  \w   -107.00 -81.00   0.50    4.00    --  -99.00 -66.00  82.53   52
 50  \w   -104.00 -78.00   0.50    4.00    --  -99.00 -72.00  55.16   52
 51  \w   -103.00 -77.00   0.50    4.00    --  -99.00 -76.00  12.31   52
 52  \w   -104.00 -78.00   0.50    4.00    --  -99.00 -72.00  49.38   52
 53  \w   -104.00 -77.00   0.50    4.00    --  -99.00 -77.00  90.00   54
 54  \w   -102.00 -76.00   0.50    4.00    --  -99.00 -76.00 147.19   52
 55  \w   -103.00 -76.00   0.50    4.00    --  -99.00 -77.00  99.31   54
 56  \w   -121.00 -60.00   0.50    2.00    --  -46.95 -21.00 152.00  122
 57  \w   -121.00 -82.00   0.50    4.00    --  -99.00 -61.00  60.00   78
 58  \w   -121.00 -86.00   0.50    4.00    --  -99.00 -46.00   7.55   70
 59  \w   -125.00 -78.00   0.50    4.00    --  -99.00 -72.00  10.09   94
 60  \w   -147.00-121.00   0.50    4.00    --  -99.00 -83.00  69.95   52
 61  \w   -151.00-126.00   0.50    4.00    --  -99.00 -21.00 152.00   50
 62  \w   -167.00-106.00   0.50    4.00    --  -99.00 -76.00 153.67  122
 63  \w   -154.00-127.00   0.50    4.00    --  -99.00 -80.00 133.75   54
 64  \w   -165.00-140.00   0.50    4.00    --  -99.00 -80.00  55.29   50
 65  \w   -166.00-139.00   0.50    4.00    --  -99.00 -76.00  12.31   54
 66  \w   -168.00-115.00   0.50    4.00    --  -99.00 -81.00  25.13  106
 67  \w   -168.00-141.00   0.50    4.00    --  -99.00 -83.00 124.61   54
 68  \w   -167.00 -86.00   0.50    4.00    --  -99.00 -47.00  68.06  162
 69  \w   -167.00-126.00   0.50    4.00    --  -99.00 -46.00   7.55   82
 70  \w   -167.00 -80.00   0.50    4.00    --  -99.00 -67.00  56.00  174
 71  \w   -167.00 -82.00   0.50    4.00    --  -99.00 -63.00 120.00  170
 72  \w   -113.00 -87.00   0.50    4.00    --  -99.00 125.00  30.00   52
 73  \w    -73.00 -27.00   0.50    4.00    --  -99.00 125.00  30.00   92
;
_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      -0.0331087000
_diffrn_orient_matrix_UB_12      0.0161806000
_diffrn_orient_matrix_UB_13      0.0636274000
_diffrn_orient_matrix_UB_21      0.0971975000
_diffrn_orient_matrix_UB_22      0.0241097000
_diffrn_orient_matrix_UB_23      0.0375600000
_diffrn_orient_matrix_UB_31      -0.0181216000
_diffrn_orient_matrix_UB_32      0.1000729000
_diffrn_orient_matrix_UB_33      -0.0194105000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            88080
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.296
_diffrn_reflns_theta_min         2.992
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54691
_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_colour            'light red'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.315
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details
;
 Flack x determined using 4589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.148(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.337
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1081
_refine_ls_number_reflns         17304
_refine_ls_number_restraints     462
_refine_ls_restrained_S_all      2.404
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.1375
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3298
_refine_ls_wR_factor_ref         0.3437
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                13005
_reflns_number_total             17304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00954_si_008.cif
_cod_data_source_block           tx635a
_cod_database_code               4134595
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     CHON
_reflns_odcompleteness_completeness 99.96
_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
 C53-C15 = C35-C34 = C39-C38 = C38-C37
 1.39 with sigma of 0.01
 Cl10-C101 = Cl11-C101 = Cl12-C101 = Cl6-C100 = Cl5-C100 = Cl4-C100
 1.76 with sigma of 0.01
 Cl8-C102 = Cl7-C102 = Cl9-C102
 1.76 with sigma of 0.01
 C85-C84 = C86-C85 = C87-C86
 1.54 with sigma of 0.01
 C78-C77 = C79-C78 = C80-C79 = C81-C80 = C81-C82 = C83-C77 = C84-C83 = C89-C88
 = C90-C89 = C90-C91 = C92-C91 = C93-C92 = C94-C88 = C94-C95 = C95-C96 = C96-
 C97 = C98-C97
 1.54 with sigma of 0.01
 C95-C97
 2.5 with sigma of 0.02
 C96-C94
 2.5 with sigma of 0.02
 Cl10-Cl12
 2.7 with sigma of 0.02
 Cl11-Cl12
 2.7 with sigma of 0.02
 Cl10-Cl11
 2.7 with sigma of 0.02
 C83-C85
 2.5 with sigma of 0.02
 C84-C86
 2.5 with sigma of 0.02
 C96-C98
 2.5 with sigma of 0.02
 C93-C91
 2.5 with sigma of 0.02
 C80-C82
 2.5 with sigma of 0.02
 C85-C87
 2.6 with sigma of 0.02
3. Rigid bond restraints
 C13, C14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N2, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C79, C80
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C30, C31
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C34, C37
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C65, C76
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C69, C70
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C84, C85
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C41, C52
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C37, C38
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N2, C88
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C35, C36
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C86, C87
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O2AA \\sim O3 \\sim N2 \\sim C10 \\sim C11: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04
Cl1 \\sim Cl2 \\sim Cl3 \\sim Cl4 \\sim Cl5 \\sim Cl6 \\sim C99 \\sim C100
\\sim Cl10 \\sim Cl11 \\sim Cl12 \\sim C101: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04
C88 \\sim C89 \\sim C90 \\sim C91 \\sim C92 \\sim C93 \\sim C94 \\sim C95 \\sim
C96 \\sim C97 \\sim C98: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81 \\sim C82 \\sim C83 \\sim C84 \\sim
C85 \\sim C86 \\sim C87: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
Uanis(O3) \\sim Ueq, Uanis(O2AA) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(Cl5) \\sim Ueq, Uanis(Cl6) \\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(Cl4)
\\sim Ueq, Uanis(Cl12) \\sim Ueq, Uanis(Cl10) \\sim Ueq, Uanis(C101) \\sim Ueq,
Uanis(Cl11) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(C99)
\\sim Ueq, Uanis(Cl3) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C102) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl9) \\sim Ueq, Uanis(Cl8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C88) \\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(C90) \\sim Ueq, Uanis(C94)
\\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C91) \\sim Ueq, Uanis(C96) \\sim Ueq,
Uanis(C98) \\sim Ueq, Uanis(C95) \\sim Ueq, Uanis(C92) \\sim Ueq, Uanis(C93)
\\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C78) \\sim Ueq, Uanis(C79) \\sim Ueq,
Uanis(C80) \\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C84)
\\sim Ueq, Uanis(C82) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(C86) \\sim Ueq,
Uanis(C87) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Riding coordinates:
 C82(H82A,H82B,H82C), C87(H87A,H87B,H87C), C93(H93A,H93B,H93C), C98(H98A,H98B,
 H98C)
5.b Ternary CH refined with riding coordinates:
 C77(H77), C88(H88), C99(H99), C100(H100), C102(H102), C101(H101)
5.c Secondary CH2 refined with riding coordinates:
 C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B), C81(H81A,H81B), C83(H83A,
 H83B), C84(H84A,H84B), C85(H85A,H85B), C86(H86A,H86B), C89(H89A,H89B),
 C90(H90A,H90B), C91(H91A,H91B), C92(H92A,H92B), C94(H94A,H94B), C95(H95A,H95B),
  C96(H96A,H96B), C97(H97A,H97B)
5.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C13(H13), C18(H18), C29(H29), C30(H30), C35(H35), C36(H36),
 C37(H37), C38(H38), C43(H43), C44(H44), C45(H45), C46(H46), C48(H48), C49(H49),
  C50(H50), C51(H51), C53(H53), C54(H54), C59(H59), C60(H60), C61(H61),
 C62(H62), C67(H67), C68(H68), C69(H69), C70(H70), C72(H72), C73(H73), C74(H74),
  C75(H75)
;
_shelx_res_checksum              66348
_shelx_hkl_checksum              20598
_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 4.442
_oxdiff_exptl_absorpt_empirical_full_min 0.292