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_4134594
_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         'C98 H78 N2 O4'
_chemical_formula_sum            'C98 H78 N2 O4'
_chemical_formula_weight         1347.62
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                70.914(2)
_cell_angle_beta                 88.7450(10)
_cell_angle_gamma                88.2070(10)
_cell_formula_units_Z            8
_cell_length_a                   16.3803(3)
_cell_length_b                   29.3997(6)
_cell_length_c                   34.6846(5)
_cell_measurement_reflns_used    45698
_cell_measurement_temperature    169.99(13)
_cell_measurement_theta_max      74.8130
_cell_measurement_theta_min      2.6830
_cell_volume                     15776.1(5)
_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(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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    -19.00   6.00   0.50    2.00    --   46.95 -73.00  60.00   50
  2  \w     21.00  47.00   0.50    2.00    --   46.95 -73.00  60.00   52
  3  \w     18.00  89.00   0.50    2.00    --   46.95-125.00  60.00  142
  4  \w     57.00  87.00   0.50    5.00    --  103.25 -73.00  60.00   60
  5  \w     45.00 115.00   0.50    5.00    --  103.25 -15.00   0.00  140
  6  \w     47.00 106.00   0.50    5.00    --  103.25 -94.00-120.00  118
  7  \w     90.00 117.00   0.50    5.00    --  103.25-125.00 -90.00   54
  8  \w     36.00  67.00   0.50    5.00    --  103.25-125.00 -90.00   62
  9  \w     42.00 117.00   0.50    5.00    --  103.25-125.00-150.00  150
 10  \w     32.00 107.00   0.50    5.00    --  103.25 -77.00-120.00  150
 11  \w     21.00  93.00   0.50    2.00    --   46.95-125.00 -90.00  144
 12  \w     32.00 103.00   0.50    5.00    --  103.25 -94.00  60.00  142
 13  \w     41.00  98.00   0.50    5.00    --  103.25 -94.00 120.00  114
 14  \w     38.00 117.00   0.50    5.00    --  103.25-125.00  60.00  158
 15  \w    143.00 168.00   0.50    5.00    --  103.25  15.00 120.00   50
 16  \w     92.00 157.00   0.50    5.00    --  103.25  45.00 150.00  130
 17  \w     31.00 112.00   0.50    2.00    --   46.95  73.00-170.00  162
 18  \w     83.00 146.00   0.50    5.00    --  103.25  73.00-170.00  126
 19  \w    -67.00  12.00   0.50    2.00    --  -46.95  73.00-170.00  158
 20  \w    -78.00 -53.00   0.50    5.00    --  -99.00  73.00-170.00   50
 21  \w   -115.00 -31.00   0.50    5.00    --  -99.00 125.00 -60.00  168
 22  \w    -92.00 -65.00   0.50    5.00    --  -99.00  45.00  30.00   54
 23  \w   -115.00 -28.00   0.50    2.00    --  -46.95 -73.00  60.00  174
 24  \w   -116.00 -71.00   0.50    2.00    --  -46.95-125.00  30.00   90
 25  \w   -162.00 -79.00   0.50    5.00    --  -99.00 -73.00  60.00  166
 26  \w   -161.00 -93.00   0.50    5.00    --  -99.00 -45.00   0.00  136
 27  \w   -157.00 -86.00   0.50    5.00    --  -99.00 -45.00 -90.00  142
 28  \w   -115.00 -71.00   0.50    2.00    --  -46.95-125.00-150.00   88
 29  \w   -164.00 -94.00   0.50    5.00    --  -99.00 -45.00 -60.00  140
;
_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      -0.0811149000
_diffrn_orient_matrix_UB_12      0.0240401000
_diffrn_orient_matrix_UB_13      0.0073237000
_diffrn_orient_matrix_UB_21      -0.0129303000
_diffrn_orient_matrix_UB_22      -0.0414875000
_diffrn_orient_matrix_UB_23      0.0402812000
_diffrn_orient_matrix_UB_31      0.0459187000
_diffrn_orient_matrix_UB_32      0.0278822000
_diffrn_orient_matrix_UB_33      0.0230893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            166904
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.049
_diffrn_reflns_theta_max         66.049
_diffrn_reflns_theta_min         2.696
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29076
_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            'fluorescent light blue'
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_description       cube
_exptl_crystal_F_000             5696
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.33
_refine_diff_density_max         1.948
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.782
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     3741
_refine_ls_number_reflns         53748
_refine_ls_number_restraints     1196
_refine_ls_restrained_S_all      23.970
_refine_ls_R_factor_all          0.2294
_refine_ls_R_factor_gt           0.1979
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_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          0.4492
_refine_ls_wR_factor_ref         0.4780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                32654
_reflns_number_total             53748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00954_si_004.cif
_cod_data_source_block           tx1116-a_sq
_cod_depositor_comments
;

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C392 H312 N8 O16'
_cod_original_formula_weight         5390.48
_cod_original_formula_moiety         '4(C98 H78 N2 O4)'
_cod_original_formula_units_Z            2
_cod_database_code               4134594
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     CHON
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.816
_reflns_odcompleteness_completeness 99.68
_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
 H10N-H7DA_$1 = H10N-H7DB_$2 = H1H-H2HB = H3HA-H5HB
 2.16 with sigma of 0.01
 H11U-H132_$3
 2.16 with sigma of 0.01
 C6A-C6C_$2
 3.25 with sigma of 0.02
 C1H-C3H = C3H-C5H = C2H-C4H = C4H-C6H = C2H-C7H
 2.54 with sigma of 0.03
 C1H-C2H = C2H-C3H = C3H-C4H = C4H-C5H = C5H-C6H
 1.53 with sigma of 0.02
 C1G-C8G = C8G-C10G = C7G-C9G = C9G-C11G
 2.54 with sigma of 0.03
 C1G-C3G = C3G-C5G = C2G-C4G = C4G-C6G = C2G-C7G
 2.54 with sigma of 0.03
 C1G-C7G = C7G-C8G = C8G-C9G
 1.53 with sigma of 0.02
 C9G-C10G = C10G-C11G
 1.53 with sigma of 0.01
 C1G-C2G = C2G-C3G = C3G-C4G = C4G-C5G = C5G-C6G
 1.53 with sigma of 0.02
 C1F-C8F = C8F-C10F = C7F-C9F = C9F-C11F
 2.54 with sigma of 0.03
 C1F-C3F = C3F-C5F = C2F-C4F = C4F-C6F = C2F-C7F
 2.54 with sigma of 0.03
 C1F-C7F = C7F-C8F = C8F-C9F = C9F-C10F = C10F-C11F
 1.53 with sigma of 0.02
 C1F-C2F = C2F-C3F = C3F-C4F = C4F-C5F = C5F-C6F
 1.53 with sigma of 0.02
 C1E-C8E = C8E-C10E = C7E-C9E = C9E-C11E
 2.54 with sigma of 0.03
 C1E-C3E = C3E-C5E = C2E-C4E = C4E-C6E = C2E-C7E
 2.54 with sigma of 0.03
 C1E-C7E = C7E-C8E = C8E-C9E = C9E-C10E = C10E-C11E
 1.53 with sigma of 0.02
 C1E-C2E = C2E-C3E = C3E-C4E = C4E-C5E = C5E-C6E
 1.53 with sigma of 0.02
 C1D-C8D = C8D-C10D = C7D-C9D = C9D-C11D
 2.54 with sigma of 0.03
 C1D-C3D = C3D-C5D = C2D-C4D = C4D-C6D = C2D-C7D
 2.54 with sigma of 0.03
 C1D-C7D = C7D-C8D = C8D-C9D = C9D-C10D = C10D-C11D
 1.53 with sigma of 0.02
 C1D-C2D = C2D-C3D = C3D-C4D = C4D-C5D = C5D-C6D
 1.53 with sigma of 0.02
 C1C-C8C = C8C-C10C = C7C-C9C = C9C-C11C
 2.54 with sigma of 0.03
 C1C-C3C = C3C-C5C = C2C-C4C = C4C-C6C = C2C-C7C
 2.54 with sigma of 0.03
 C1C-C7C = C7C-C8C = C8C-C9C = C9C-C10C = C10C-C11C
 1.53 with sigma of 0.02
 C1C-C2C = C2C-C3C = C3C-C4C = C4C-C5C = C5C-C6C
 1.53 with sigma of 0.02
 C1B-C8B = C8B-C10B = C7B-C9B = C9B-C11B
 2.54 with sigma of 0.03
 C1B-C3B = C3B-C5B = C2B-C4B = C4B-C6B = C2B-C7B
 2.54 with sigma of 0.03
 C1B-C7B = C7B-C8B = C8B-C9B = C9B-C10B = C10B-C11B
 1.53 with sigma of 0.02
 C1B-C2B = C2B-C3B = C3B-C4B = C4B-C5B = C5B-C6B
 1.53 with sigma of 0.02
 C1A-C8A = C8A-C10A = C7A-C9A = C9A-C11A
 2.54 with sigma of 0.03
 C1A-C3A = C3A-C5A = C2A-C4A = C4A-C6A = C2A-C7A
 2.54 with sigma of 0.03
 C1A-C7A = C7A-C8A = C8A-C9A = C9A-C10A = C10A-C11A
 1.53 with sigma of 0.02
 C1A-C2A = C2A-C3A = C3A-C4A = C4A-C5A = C5A-C6A
 1.53 with sigma of 0.02
 C1H-C8H = C8H-C10H = C7H-C9H = C9H-C11H
 2.54 with sigma of 0.03
 C1H-C7H = C7H-C8H = C8H-C9H = C9H-C10H = C10H-C11H
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C5C \\sim C6C \\sim C146 \\sim C297: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A \\sim C8A \\sim
C9A \\sim C10A \\sim C11A \\sim C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B
\\sim C6B \\sim C7B \\sim C8B \\sim C9B \\sim C10B \\sim C11B \\sim C1C \\sim
C2C \\sim C3C \\sim C4C \\sim C5C \\sim C6C \\sim C7C \\sim C8C \\sim C9C \\sim
C10C \\sim C11C \\sim C1D \\sim C2D \\sim C3D \\sim C4D \\sim C5D \\sim C6D
\\sim C7D \\sim C8D \\sim C9D \\sim C10D \\sim C11D \\sim C1E \\sim C2E \\sim
C3E \\sim C4E \\sim C5E \\sim C6E \\sim C7E \\sim C8E \\sim C9E \\sim C10E
\\sim C11E \\sim C1F \\sim C2F \\sim C3F \\sim C4F \\sim C5F \\sim C6F \\sim
C7F \\sim C8F \\sim C9F \\sim C10F \\sim C11F \\sim C1G \\sim C2G \\sim C3G
\\sim C4G \\sim C5G \\sim C6G \\sim C7G \\sim C8G \\sim C9G \\sim C10G \\sim
C11G \\sim C1H \\sim C2H \\sim C3H \\sim C4H \\sim C5H \\sim C6H \\sim C7H
\\sim C8H \\sim C9H \\sim C10H \\sim C11H: within 3.8A with sigma of 0.02 and
sigma for terminal atoms of 0.04
4. Others
 Fixed U11: C11G(0.206445)
 Fixed X: C7D(0.32203) C10G(0.471429)
 Fixed Y: C10G(0.779509)
5.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C1E(H1E), C1F(H1F), C1G(H1G), C1H(H1H)
5.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C7A(H7AA,
 H7AB), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10A,H10B), C2B(H2BA,H2BB),
 C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB),
  C9B(H9BA,H9BB), C10B(H10C,H10D), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C4C(H4CA,
 H4CB), C5C(H5CA,H5CB), C7C(H7CA,H7CB), C8C(H8CA,H8CB), C9C(H9CA,H9CB),
 C10C(H10E,H10F), C2D(H2DA,H2DB), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C5D(H5DA,
 H5DB), C7D(H7DA,H7DB), C8D(H8DA,H8DB), C9D(H9DA,H9DB), C10D(H10G,H10H),
 C2E(H2EA,H2EB), C3E(H3EA,H3EB), C4E(H4EA,H4EB), C5E(H5EA,H5EB), C7E(H7EA,H7EB),
  C8E(H8EA,H8EB), C9E(H9EA,H9EB), C10E(H10I,H10J), C2F(H2FA,H2FB), C3F(H3FA,
 H3FB), C4F(H4FA,H4FB), C5F(H5FA,H5FB), C7F(H7FA,H7FB), C8F(H8FA,H8FB),
 C9F(H9FA,H9FB), C10F(H10K,H10L), C2G(H2GA,H2GB), C3G(H3GA,H3GB), C4G(H4GA,
 H4GB), C5G(H5GA,H5GB), C7G(H7GA,H7GB), C8G(H8GA,H8GB), C9G(H9GA,H9GB),
 C10G(H10M,H10N), C2H(H2HA,H2HB), C3H(H3HA,H3HB), C4H(H4HA,H4HB), C5H(H5HA,
 H5HB), C7H(H7HA,H7HB), C8H(H8HA,H8HB), C9H(H9HA,H9HB), C10H(H10O,H10P)
5.c Me refined with riding coordinates:
 C6A(H6AA,H6AB,H6AC), C11A(H11A,H11B,H11C), C6B(H6BA,H6BB,H6BC), C11B(H11D,
 H11E,H11F), C6C(H6CA,H6CB,H6CC), C11C(H11G,H11H,H11I), C6D(H6DA,H6DB,H6DC),
 C11D(H11J,H11K,H11L), C6E(H6EA,H6EB,H6EC), C11E(H11M,H11N,H11O), C6F(H6FA,H6FB,
 H6FC), C11F(H11P,H11Q,H11R), C6G(H6GA,H6GB,H6GC), C11G(H11S,H11T,H11U),
 C6H(H6HA,H6HB,H6HC), C11H(H11V,H11W,H11X)
5.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20),
 C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31),
  C39(H39), C47(H47), C52(H52), C55(H55), C56(H56), C58(H58), C59(H59),
 C61(H61), C62(H62), C65(H65), C66(H66), C69(H69), C70(H70), C72(H72), C73(H73),
  C74(H74), C75(H75), C81(H81), C89(H89), C90(H90), C91(H91), C92(H92),
 C94(H94), C95(H95), C97(H97), C98(H98), C100(H100), C101(H101), C103(H103),
 C104(H104), C106(H106), C107(H107), C110(H110), C120(H120), C124(H124),
 C129(H129), C130(H130), C132(H132), C133(H133), C135(H135), C136(H136),
 C139(H139), C140(H140), C143(H143), C144(H144), C146(H146), C147(H147),
 C148(H148), C149(H149), C161(H161), C162(H162), C171(H171), C176(H176),
 C177(H177), C178(H178), C180(H180), C181(H181), C183(H183), C184(H184),
 C186(H186), C187(H187), C193(H193), C194(H194), C195(H195), C196(H196),
 C200(H200), C205(H205), C206(H206), C208(H208), C209(H209), C214(H214),
 C215(H215), C216(H216), C217(H217), C219(H219), C220(H220), C222(H222),
 C223(H223), C225(H225), C226(H226), C227(H227), C237(H237), C240(H240),
 C241(H241), C243(H243), C244(H244), C246(H246), C247(H247), C249(H249),
 C250(H250), C252(H252), C253(H253), C255(H255), C256(H256), C257(H257),
 C258(H258), C266(H266), C273(H273), C275(H275), C282(H282), C283(H283),
 C285(H285), C286(H286), C288(H288), C289(H289), C290(H290), C291(H291),
 C294(H294), C295(H295), C297(H297), C298(H298), C299(H299), C300(H300)
;
_shelx_res_checksum              25833
_shelx_hkl_checksum              81408
_shelx_fab_checksum              39627
_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 3.162
_oxdiff_exptl_absorpt_empirical_full_min 0.331