Stereoselective synthesis of [2.2]triphenylenophanes <i>via</i> intramolecular double [2 + 2 + 2] cycloadditions.
Kawai, Yuya; Nogami, Juntaro; Nagashima, Yuki; Tanaka, Ken; Chemical science 14 (2023) 3963–3972; doi:10.1039/d3sc00571b

data_1568628
_publ_section_title
;
 Stereoselective synthesis of [2.2]triphenylenophanes <i>via</i>
 intramolecular double [2 + 2 + 2] cycloadditions.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              3963
_journal_page_last               3972
_journal_paper_doi               10.1039/d3sc00571b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C70 H52 O2'
_chemical_formula_sum            'C70 H52 O2'
_chemical_formula_weight         925.11
_chemical_name_common            (+-)-3e
_chemical_name_systematic        '[2.2][5]Helicenophane'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-23
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-01-25 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.506(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9227(4)
_cell_length_b                   24.0368(7)
_cell_length_c                   17.1320(5)
_cell_measurement_reflns_used    12231
_cell_measurement_temperature    210
_cell_measurement_theta_max      28.0240
_cell_measurement_theta_min      2.0780
_cell_volume                     5275.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_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     85.00 110.00   0.50   84.92    --   20.00  54.00 -30.00   50
  2  \w    -70.00 -15.00   0.50   84.92    --   20.00  54.00 120.00  110
  3  \w     43.00  72.00   0.50   84.92    --   20.00  54.00 120.00   58
  4  \w     76.00 109.00   0.50   84.92    --   20.00  54.00 120.00   66
  5  \w    -74.00 107.00   0.50   84.92    --   20.00  54.00-120.00  362
  6  \w    -42.00   6.00   0.50   84.92    --   20.00  54.00-150.00   96
  7  \w     18.00  43.00   0.50   84.92    --   20.00  54.00-150.00   50
  8  \w     70.00  97.00   0.50   84.92    --   20.00  54.00-150.00   54
  9  \w    -17.00  83.00   0.50   84.92    --   20.00  54.00-180.00  200
 10  \w     11.00  36.00   0.50   84.92    --   20.00  54.00  60.00   50
 11  \w     75.00 100.00   0.50   84.92    --   20.00  54.00  60.00   50
 12  \w    -62.00 -33.00   0.50   84.92    --   20.00  54.00 -30.00   58
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II (JP)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0521125000
_diffrn_orient_matrix_UB_12      -0.0087385000
_diffrn_orient_matrix_UB_13      -0.0015775000
_diffrn_orient_matrix_UB_21      -0.0186695000
_diffrn_orient_matrix_UB_22      -0.0248576000
_diffrn_orient_matrix_UB_23      -0.0192206000
_diffrn_orient_matrix_UB_31      -0.0006162000
_diffrn_orient_matrix_UB_32      0.0132720000
_diffrn_orient_matrix_UB_33      -0.0370459000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            55196
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.653
_diffrn_reflns_theta_min         2.324
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.61a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.172
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         15579
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0765
_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^)+(0.0931P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.1958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7720
_reflns_number_total             15579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00571b2.cif
_cod_data_source_block           exp_529_auto
_cod_depositor_comments
'Adding full bibliography for 1568627--1568628.cif.'
_cod_database_code               1568628
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Restrained distances
 C70-C71 \\sim C70-C71A
 with sigma of 0.02
 C70-C34 \\sim C70-C34A
 with sigma of 0.04
 C71-C34 \\sim C71A-C34A
 with sigma of 0.02
2. Others
 Sof(H70C)=Sof(H70D)=Sof(C71A)=Sof(H71C)=Sof(H71D)=Sof(C34A)=Sof(H34D)=
 Sof(H34E)=Sof(H34F)=1-FVAR(1)
 Sof(H70A)=Sof(H70B)=Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(C34)=Sof(H34A)=Sof(H34B)=
 Sof(H34C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C35(H35A,H35B), C33(H33A,H33B), C69(H69A,H69B), C62(H62A,
 H62B), C63(H63A,H63B), C70(H70A,H70B), C70(H70C,H70D), C71(H71A,H71B),
 C71A(H71C,H71D)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C39(H39), C10(H10), C28(H28), C18(H18), C40(H40), C17(H17),
 C21(H21), C7(H7), C24(H24), C59(H59), C9(H9), C23(H23), C46(H46), C8(H8),
 C43(H43), C65(H65), C22(H22), C44(H44), C68(H68), C57(H57), C45(H45), C58(H58),
  C56(H56), C50(H50), C66(H66), C67(H67), C53(H53), C51(H51), C52(H52)
3.c Idealised Me refined as rotating group:
 C64(H64A,H64B,H64C), C34(H34A,H34B,H34C), C34A(H34D,H34E,H34F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              73912
_shelx_fab_checksum              94857
_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 1.175
_oxdiff_exptl_absorpt_empirical_full_min 0.778