Lemniscular carbon nanohoops with contiguous conjugation from planar chiral [2.2]paracyclophane: influence of the regioselective synthesis on topological chirality.
He, Jing; Yu, Mo-Han; Lian, Zhe; Fan, Yan-Qing; Guo, Sheng-Zhu; Li, Xiao-Nan; Wang, Ying; Wang, Wen-Guang; Cheng, Zhi-Yun; Jiang, Hua; Chemical science 14 (2023) 4426–4433; doi:10.1039/d2sc06825g

data_1568718
_publ_section_title
;
 Lemniscular carbon nanohoops with contiguous conjugation from planar
 chiral [2.2]paracyclophane: influence of the regioselective synthesis on
 topological chirality.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              4426
_journal_page_last               4433
_journal_paper_doi               10.1039/d2sc06825g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C104 H84 O8'
_chemical_formula_sum            'C104 H84 O8'
_chemical_formula_weight         1461.71
_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
_audit_creation_date             2022-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-18 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                94.4940(10)
_cell_angle_beta                 95.4560(10)
_cell_angle_gamma                112.361(2)
_cell_formula_units_Z            2
_cell_length_a                   13.7107(2)
_cell_length_b                   16.2983(3)
_cell_length_c                   21.2715(3)
_cell_measurement_reflns_used    35940
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.0240
_cell_measurement_theta_min      3.3880
_cell_volume                     4342.02(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_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    -65.00  21.00   0.50    0.60    --  -48.75  72.00  61.00  172
  2  \w   -111.00 -62.00   0.50    0.60    --  -48.75 -72.00 -68.00   98
  3  \w     47.00 111.00   0.50    0.60    --   48.75  72.00  61.00  128
  4  \w   -174.00-111.00   0.50    2.41    -- -102.00 -72.00 -68.00  126
  5  \w    -88.00 -42.00   0.50    2.41    -- -102.00  72.00  61.00   92
  6  \w   -109.00 -83.00   0.50    2.41    -- -102.00 -72.00 -68.00   52
  7  \w     85.00 174.00   0.50    2.41    --  102.75  72.00  61.00  178
  8  \w     44.00  90.00   0.50    2.41    --  102.75 -72.00 -68.00   92
  9  \w    -11.00  17.00   0.50    0.60    --  -48.75  19.00  30.00   56
 10  \w    -22.00  46.00   0.50    0.60    --   48.75 -72.00 -68.00  136
 11  \w     19.00  87.00   0.50    0.60    --   48.75-125.00 -30.00  136
 12  \w     95.00 121.00   0.50    0.60    --   48.75 125.00 150.00   52
 13  \w    -24.00  28.00   0.50    0.60    --   48.75 -19.00 120.00  104
 14  \w     83.00 116.00   0.50    0.60    --   48.75 125.00 -90.00   66
 15  \w     84.00 121.00   0.50    0.60    --   48.75 125.00   0.00   74
 16  \w    -57.00 -32.00   0.50    2.41    -- -102.00  57.00 150.00   50
 17  \w   -108.00 -81.00   0.50    2.41    -- -102.00 -77.00 -90.00   54
 18  \w    -62.00 -36.00   0.50    2.41    -- -102.00  57.00 -90.00   52
 19  \w   -169.00-119.00   0.50    2.41    -- -102.00 -77.00 -90.00  100
 20  \w   -112.00 -82.00   0.50    2.41    -- -102.00 -77.00-180.00   60
 21  \w   -166.00-122.00   0.50    2.41    -- -102.00 -77.00-180.00   88
 22  \w   -105.00 -31.00   0.50    2.41    -- -102.00 125.00  60.00  148
 23  \w   -173.00 -99.00   0.50    2.41    -- -102.00 -37.00 150.00  148
 24  \w     57.00  82.00   0.50    2.41    --  102.75 -77.00  30.00   50
 25  \w     31.00 115.00   0.50    2.41    --  102.75-125.00-150.00  168
 26  \w     31.00 109.00   0.50    2.41    --  102.75 -99.00-150.00  156
 27  \w     50.00 115.00   0.50    2.41    --  102.75-125.00  60.00  130
 28  \w     43.00 105.00   0.50    2.41    --  102.75 -99.00 -90.00  124
 29  \w     71.00 105.00   0.50    2.41    --  102.75 -99.00 120.00   68
 30  \w     45.00 116.00   0.50    2.41    --  102.75-125.00 150.00  142
 31  \w     61.00  88.00   0.50    2.41    --  102.75 -99.00  30.00   54
 32  \w    101.00 167.00   0.50    2.41    --  102.75  57.00 -30.00  132
 33  \w     41.00  66.00   0.50    2.41    --  102.75 -57.00-180.00   50
 34  \w     78.00 114.00   0.50    2.41    --  102.75-125.00   0.00   72
 35  \w     31.00  56.00   0.50    2.41    --  102.75 -57.00-150.00   50
 36  \w     31.00  57.00   0.50    2.41    --  102.75-125.00-120.00   52
 37  \w     87.00 112.00   0.50    2.41    --  102.75-125.00-120.00   50
 38  \w     36.00  70.00   0.50    2.41    --  102.75-125.00   0.00   68
 39  \w     90.00 165.00   0.50    2.41    --  102.75  57.00   0.00  150
 40  \w     35.00  64.00   0.50    2.41    --  102.75 -57.00  90.00   58
 41  \w     62.00  92.00   0.50    2.41    --  102.75 -99.00 -60.00   60
 42  \w     37.00  64.00   0.50    2.41    --  102.75 -57.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0154635000
_diffrn_orient_matrix_UB_12      0.0508863000
_diffrn_orient_matrix_UB_13      -0.0587464000
_diffrn_orient_matrix_UB_21      -0.1070388000
_diffrn_orient_matrix_UB_22      0.0093293000
_diffrn_orient_matrix_UB_23      0.0037424000
_diffrn_orient_matrix_UB_31      0.0578040000
_diffrn_orient_matrix_UB_32      0.0890747000
_diffrn_orient_matrix_UB_33      0.0437165000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            55712
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.347
_diffrn_reflns_theta_min         3.408
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'fluorescent light white'
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description       needle
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1017
_refine_ls_number_reflns         17529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0913
_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^)+(0.0426P)^2^+19.6234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2200
_refine_ls_wR_factor_ref         0.2275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15073
_reflns_number_total             17529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06825g2.cif
_cod_data_source_block           20220217a_auto
_cod_depositor_comments
'Adding full bibliography for 1568718--1568719.cif.'
_cod_original_cell_volume        4342.01(13)
_cod_database_code               1568718
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O'
_diffrn_oxdiff_digest_frames
;
01a20160b9ba7d7eaf7c6c572db561ceea00036e4a3
;
_diffrn_oxdiff_digest_hkl
;
017cdfd18e242c6f9bb838b0f68b0dd583301b
;
_reflns_odcompleteness_completeness 99.86
_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.a Secondary CH2 refined with riding coordinates:
 C00W(H00A,H00B), C44(H44A,H44B), C01S(H01A,H01B), C45(H45A,H45B)
2.b Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C71(H71), C77(H77), C00Q(H00Q), C86(H86), C147(H147), C60(H60),
 C155(H155), C68(H68), C101(H101), C57(H57), C72(H72), C58(H58), C78(H78),
 C96(H96), C73(H73), C99(H99), C85(H85), C61(H61), C103(H103), C114(H114),
 C109(H109), C80(H80), C84(H84), C111(H111), C136(H136), C01V(H01V), C128(H128),
  C112(H112), C102(H102), C87(H87), C116(H116), C79(H79), C67(H67), C028(H028),
 C108(H108), C130(H130), C65(H65), C141(H141), C02F(H02F), C115(H115),
 C117(H117), C137(H137), C153(H153), C66(H66), C122(H122), C123(H123),
 C131(H131), C125(H125), C124(H124), C142(H142), C129(H129)
2.c Idealised Me refined as rotating group:
 C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C76(H76A,H76B,H76C), C140(H14A,H14B,
 H14C), C119(H11A,H11B,H11C), C118(H11D,H11E,H11F), C82(H82A,H82B,H82C),
 C139(H13A,H13B,H13C)
;
_shelx_res_checksum              39143
_shelx_hkl_checksum              10172
_shelx_fab_checksum              97484
_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 4.574
_oxdiff_exptl_absorpt_empirical_full_min 0.270