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_4134593
_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_formula_moiety         'C H Cl3, C98 H78 N2 O4'
_chemical_formula_sum            'C99 H79 Cl3 N2 O4'
_chemical_formula_weight         1466.99
_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             2019-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                69.440(2)
_cell_angle_beta                 82.721(2)
_cell_angle_gamma                80.7830(10)
_cell_formula_units_Z            1
_cell_length_a                   7.71580(10)
_cell_length_b                   15.2504(3)
_cell_length_c                   16.7377(3)
_cell_measurement_reflns_used    33457
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      74.8720
_cell_measurement_theta_min      2.7810
_cell_volume                     1814.96(6)
_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      169.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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     -1.00  45.00   0.50    1.00    --   26.00  86.00  97.65   92
  2  \w     24.00 119.00   0.50    1.00    --   46.95  77.00 120.00  190
  3  \w     73.00 119.00   0.50    1.00    --   46.95 131.00 122.00   92
  4  \w     73.00 169.00   0.50    3.00    --  103.25 131.00 122.00  192
  5  \w    103.00 136.00   0.50    3.00    --   90.00  67.00 -37.85   66
  6  \w     69.00 119.00   0.50    1.00    --   46.95 138.00 -62.00  100
  7  \w     69.00 169.00   0.50    3.00    --  103.25 138.00 -62.00  200
  8  \w     71.00  97.00   0.50    3.00    --   90.00  67.00 -37.85   52
  9  \w     42.00  75.00   0.50    1.00    --   66.00  83.00 -11.50   66
 10  \w     31.00  64.00   0.50    1.00    --   54.00  81.00 -24.36   66
 11  \w     36.00  72.00   0.50    1.00    --   58.00  76.00   3.75   72
 12  \w     47.00  82.00   0.50    1.00    --   70.00  79.00  54.29   70
 13  \w     33.00  69.00   0.50    1.00    --   54.00  75.00 157.53   72
 14  \w     32.00  57.00   0.50    1.00    --   54.00  77.00 131.43   50
 15  \w     36.00  62.00   0.50    1.00    --   58.00  76.00  81.42   52
 16  \w     37.00  62.00   0.50    1.00    --   58.00  76.00  58.21   50
 17  \w     35.00  61.00   0.50    1.00    --   58.00  77.00  16.43   52
 18  \w     26.00 122.00   0.50    1.00    --   50.00  81.00 -65.42  192
 19  \w     41.00  66.00   0.50    1.00    --   62.00  75.00-156.33   50
 20  \w     38.00  65.00   0.50    1.00    --   62.00  80.00-107.85   54
 21  \w     48.00  73.00   0.50    1.00    --   70.00  78.00 -75.84   50
 22  \w     34.00 121.00   0.50    1.00    --   46.95  19.00 -90.00  174
 23  \w     26.00 122.00   0.50    1.00    --   50.00  80.00-114.75  192
 24  \w     32.00  75.00   0.50    3.00    --  103.25 -45.00-180.00   86
 25  \w     32.00 125.00   0.50    3.00    --  103.25 -77.00-150.00  186
 26  \w     31.00 126.00   0.50    3.00    --  103.25-138.00-123.00  190
 27  \w     31.00 121.00   0.50    3.00    --  103.25-131.00  51.00  180
 28  \w     45.00 116.00   0.50    3.00    --  103.25-125.00  90.00  142
 29  \w     32.00 120.00   0.50    3.00    --  103.25 -61.00  30.00  176
 30  \w     20.00  98.00   0.50    1.00    --   46.95-131.00  51.00  156
 31  \w     24.00 102.00   0.50    1.00    --   46.95-138.00-123.00  156
 32  \w     25.00 122.00   0.50    1.00    --   50.00  82.00-155.68  194
 33  \w     11.00  37.00   0.50    1.00    --   42.00  94.00   3.96   52
 34  \w    -45.00 -14.00   0.50    1.00    --    6.00 132.00  43.55   62
 35  \w    -64.00 -33.00   0.50    1.00    --   10.00 171.00 -39.11   62
 36  \w     -3.00  29.00   0.50    1.00    --   30.00  98.00-148.50   64
 37  \w    -87.00 -51.00   0.50    1.00    --  -70.00 -68.00  -0.51   72
 38  \w    -79.00 -53.00   0.50    3.00    --  -78.00 -81.00  46.15   52
 39  \w    -67.00 -41.00   0.50    1.00    --  -66.00 -83.00  92.89   52
 40  \w    -63.00 -37.00   0.50    1.00    --  -62.00 -82.00 121.21   52
 41  \w    -77.00 -51.00   0.50    3.00    --  -74.00 -80.00 131.82   52
 42  \w    -79.00 -53.00   0.50    3.00    --  -78.00 -81.00 160.30   52
 43  \w    -83.00 -57.00   0.50    3.00    --  -82.00 -83.00 117.17   52
 44  \w    -85.00 -40.00   0.50    1.00    --  -62.00 -74.00 157.86   90
 45  \w    -89.00 -52.00   0.50    3.00    --  -78.00 -83.00  83.11   74
 46  \w    -91.00 -60.00   0.50    3.00    --  -82.00 -74.00  62.64   62
 47  \w    -84.00 -57.00   0.50    3.00    --  -82.00 -82.00 -21.64   54
 48  \w    -70.00 -40.00   0.50    1.00    --  -62.00 -74.00 -84.32   60
 49  \w    -72.00 -46.00   0.50    1.00    --  -70.00 -82.00-134.06   52
 50  \w    -71.00 -45.00   0.50    1.00    --  -70.00 -81.00-174.59   52
 51  \w    -82.00 -56.00   0.50    3.00    --  -82.00 -83.00-112.65   52
 52  \w    -81.00 -52.00   0.50    3.00    --  -78.00 -83.00 -72.43   58
 53  \w    -81.00 -56.00   0.50    3.00    --  -82.00 -83.00 -50.49   50
 54  \w    -87.00 -61.00   0.50    3.00    --  -82.00 -72.00 -12.95   52
 55  \w    -91.00 -65.00   0.50    3.00    --  -86.00 -73.00 -37.17   52
 56  \w    -94.00 -60.00   0.50    3.00    --  -86.00 -83.00  24.22   68
 57  \w    -92.00 -65.00   0.50    3.00    --  -86.00 -73.00  79.78   54
 58  \w    -88.00 -60.00   0.50    3.00    --  -86.00 -83.00 167.86   56
 59  \w    -94.00 -68.00   0.50    3.00    --  -86.00 -64.00 177.60   52
 60  \w   -120.00 -34.00   0.50    1.00    --  -46.95 -38.00  90.00  172
 61  \w   -104.00 -72.00   0.50    3.00    --  -90.00 -66.00  38.68   64
 62  \w   -109.00 -82.00   0.50    3.00    --  -99.00 -63.00  69.39   54
 63  \w   -110.00 -77.00   0.50    3.00    --  -99.00 -74.00  11.33   66
 64  \w   -106.00 -81.00   0.50    3.00    --  -99.00 -65.00 -68.86   50
 65  \w    -92.00 -59.00   0.50    3.00    --  -82.00 -78.00-105.81   66
 66  \w    -90.00 -63.00   0.50    3.00    --  -86.00 -83.00-123.87   54
 67  \w   -100.00 -73.00   0.50    3.00    --  -90.00 -66.00 -91.91   54
 68  \w   -117.00 -69.00   0.50    3.00    --  -90.00 -75.00-118.24   96
 69  \w   -112.00 -79.00   0.50    3.00    --  -99.00 -69.00-174.66   66
 70  \w   -119.00 -62.00   0.50    1.00    --  -46.95-138.00-123.00  114
 71  \w   -127.00 -74.00   0.50    3.00    --  -90.00 -60.00-166.37  106
 72  \w   -128.00 -80.00   0.50    3.00    --  -99.00 -70.00 -83.67   96
 73  \w   -119.00 -67.00   0.50    1.00    --  -46.95-131.00  51.00  104
 74  \w   -150.00 -72.00   0.50    3.00    --  -94.00 -76.00 -28.36  156
 75  \w   -139.00-113.00   0.50    3.00    --  -99.00 -63.00  69.39   52
 76  \w   -151.00 -96.00   0.50    3.00    --  -82.00 -74.00  62.64  110
 77  \w   -138.00 -78.00   0.50    3.00    --  -99.00 -77.00 156.39  120
 78  \w   -142.00 -81.00   0.50    3.00    --  -99.00 -77.00 150.00  122
 79  \w   -159.00 -73.00   0.50    3.00    --  -99.00 -83.00 130.35  172
 80  \w   -168.00 -67.00   0.50    3.00    --  -99.00-131.00  51.00  202
 81  \w   -158.00-123.00   0.50    3.00    --  -86.00 -73.00 -37.17   70
 82  \w   -167.00-131.00   0.50    3.00    --  -99.00 -70.00 -83.67   72
 83  \w   -162.00-122.00   0.50    3.00    --  -99.00 -65.00 -68.86   80
 84  \w   -163.00 -76.00   0.50    3.00    --  -99.00 -77.00   0.00  174
 85  \w   -157.00-128.00   0.50    3.00    --  -90.00 -60.00-166.37   58
 86  \w   -167.00 -75.00   0.50    3.00    --  -99.00 -79.00-106.77  184
 87  \w   -168.00 -62.00   0.50    3.00    --  -99.00-138.00-123.00  212
 88  \w   -166.00 -77.00   0.50    3.00    --  -99.00 -78.00  46.84  178
 89  \w   -163.00 -76.00   0.50    3.00    --  -99.00 -78.00 113.28  174
 90  \w   -161.00 -73.00   0.50    3.00    --  -99.00 -83.00 175.02  176
 91  \w   -167.00 -83.00   0.50    3.00    --  -99.00 -63.00  55.00  168
 92  \w   -112.00 -27.00   0.50    3.00    --  -99.00  61.00 -30.00  170
 93  \w   -102.00 -17.00   0.50    1.00    --  -46.95 138.00 -62.00  170
 94  \w      7.00  37.00   0.50    1.00    --   38.00  94.00 177.15   60
 95  \w    -98.00 -14.00   0.50    1.00    --  -46.95 131.00 122.00  168
 96  \w   -121.00 -26.00   0.50    3.00    --  -99.00 131.00 122.00  190
 97  \w   -126.00 -26.00   0.50    3.00    --  -99.00 138.00 -62.00  200
 98  \w   -111.00 -28.00   0.50    3.00    --  -99.00  45.00-180.00  166
 99  \w   -166.00 -76.00   0.50    3.00    --  -99.00 -77.00-141.14  180
;
_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      0.1853967000
_diffrn_orient_matrix_UB_12      0.0279801000
_diffrn_orient_matrix_UB_13      -0.0052623000
_diffrn_orient_matrix_UB_21      0.0036549000
_diffrn_orient_matrix_UB_22      0.0376062000
_diffrn_orient_matrix_UB_23      -0.0984224000
_diffrn_orient_matrix_UB_31      -0.0822752000
_diffrn_orient_matrix_UB_32      0.0981149000
_diffrn_orient_matrix_UB_33      0.0022993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            64481
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.081
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42327
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             770
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     572
_refine_ls_number_reflns         7216
_refine_ls_number_restraints     309
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1330P)^2^+0.8104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2179
_refine_ls_wR_factor_ref         0.2227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6490
_reflns_number_total             7216
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00954_si_006.cif
_cod_data_source_block           tx573a
_cod_database_code               4134593
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     CHON
_reflns_odcompleteness_completeness 99.95
_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
 Cl1-C50 = Cl3-C50 = Cl2-C50
 1.76 with sigma of 0.01
 C49A-C48A = C48A-C47A = C47A-C46 = C46-C45 = C45-C39
 1.54 with sigma of 0.01
 C47A-C49A
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim Cl1 \\sim C50 \\sim Cl3: within 1.9A with sigma of 0.02 and sigma for
terminal atoms of 0.04
C41 \\sim C42 \\sim C43 \\sim C44 \\sim C40A \\sim C42A \\sim C44A \\sim C40:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49 \\sim C45A \\sim C47A \\sim C48A
\\sim C49A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C50) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl3)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C40A) \\sim Ueq, Uanis(C42A) \\sim Ueq,
Uanis(C44A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C45) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49)
\\sim Ueq, Uanis(C45A) \\sim Ueq, Uanis(C47A) \\sim Ueq, Uanis(C48A) \\sim Ueq,
Uanis(C49A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H39A)=Sof(H41C)=Sof(H41D)=Sof(H43C)=Sof(H43D)=Sof(C40A)=Sof(H40C)=
 Sof(H40D)=Sof(C42A)=Sof(H42C)=Sof(H42D)=Sof(C44A)=Sof(H44D)=Sof(H44E)=
 Sof(H44F)=1-FVAR(1)
 Sof(H39)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=
 Sof(H42B)=Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(1)
 Sof(H46C)=Sof(H46D)=Sof(C45A)=Sof(H45C)=Sof(H45D)=Sof(C47A)=Sof(H47C)=
 Sof(H47D)=Sof(C48A)=Sof(H48C)=Sof(H48D)=Sof(C49A)=Sof(H49D)=Sof(H49E)=
 Sof(H49F)=1-FVAR(2)
 Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H46A)=Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=FVAR(2)
 Fixed Sof: Cl1(0.5) Cl2(0.5) Cl3(0.5) C50(0.5) H50(0.5)
5.a Riding coordinates:
 C44(H44A,H44B,H44C), C49(H49A,H49B,H49C)
5.b Ternary CH refined with riding coordinates:
 C50(H50), C39(H39), C39(H39A)
5.c Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C41(H41A,H41B), C41(H41C,H41D), C42(H42A,H42B), C43(H43A,
 H43B), C43(H43C,H43D), C45(H45A,H45B), C46(H46A,H46B), C46(H46C,H46D),
 C47(H47A,H47B), C48(H48A,H48B), C40A(H40C,H40D), C42A(H42C,H42D), C45A(H45C,
 H45D), C47A(H47C,H47D), C48A(H48C,H48D)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C15(H15), C16(H16), C21(H21), C22(H22), C23(H23), C24(H24),
 C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37)
5.e Idealised Me refined as rotating group:
 C44A(H44D,H44E,H44F), C49A(H49D,H49E,H49F)
;
_shelx_res_checksum              67792
_shelx_hkl_checksum              34424
_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 2.966
_oxdiff_exptl_absorpt_empirical_full_min 0.291