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_1568627
_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         'C58 H46 N2 O6 S2'
_chemical_formula_sum            'C58 H46 N2 O6 S2'
_chemical_formula_weight         931.09
_chemical_name_common            (+-)-3a
_chemical_name_systematic        '[2.2]Triphenylenophane'
_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             2023-01-17
_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                 96.463(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3238(6)
_cell_length_b                   20.1104(7)
_cell_length_c                   16.9292(7)
_cell_measurement_reflns_used    9694
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      29.4010
_cell_measurement_theta_min      1.8740
_cell_volume                     4507.3(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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.949
_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    -43.00 -17.50   0.50  418.85    --   20.00  54.00-153.20   51
  2  \w      5.00 109.50   0.50  418.85    --   20.00  54.00-153.20  209
  3  \w    -74.00 -44.50   0.50  418.85    --   20.00  54.00 120.00   59
  4  \w    -38.00  44.50   0.50  418.85    --   20.00  54.00 120.00  165
  5  \w     61.00  86.50   0.50  418.85    --   20.00  54.00 120.00   51
  6  \w    -73.00 -30.50   0.50  418.85    --   20.00  54.00   0.00   85
  7  \w     -7.00 107.50   0.50  418.85    --   20.00  54.00   0.00  229
  8  \w     45.00  81.50   0.50  418.85    --   20.00  54.00  26.80   73
  9  \w    -64.00 -27.50   0.50  418.85    --   20.00  54.00  30.00   73
 10  \w     60.00  84.50   0.50  418.85    --   20.00  54.00  30.00   49
 11  \w    -18.00   6.50   0.50  418.85    --   20.00  54.00  90.00   49
 12  \w     76.00 100.50   0.50  418.85    --   20.00  54.00  90.00   49
 13  \w    -69.00 -44.50   0.50  418.85    --   20.00  54.00-153.20   49
;
_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      0.0535457000
_diffrn_orient_matrix_UB_12      -0.0005799000
_diffrn_orient_matrix_UB_13      0.0062256000
_diffrn_orient_matrix_UB_21      0.0012634000
_diffrn_orient_matrix_UB_22      0.0343783000
_diffrn_orient_matrix_UB_23      -0.0092423000
_diffrn_orient_matrix_UB_31      -0.0017182000
_diffrn_orient_matrix_UB_32      0.0078991000
_diffrn_orient_matrix_UB_33      0.0406404000
_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  0.1102
_diffrn_reflns_av_unetI/netI     0.1103
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            44991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.604
_diffrn_reflns_theta_min         2.297
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.955
_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    1.372
_exptl_crystal_description       plate
_exptl_crystal_F_000             1952
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         13167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0633
_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^)+(0.0761P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7369
_reflns_number_total             13167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00571b2.cif
_cod_data_source_block           exp_403_autored
_cod_depositor_comments
'Adding full bibliography for 1568627--1568628.cif.'
_cod_database_code               1568627
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C232 H184 N8 O24 S8 '
_chemical_oxdiff_usercomment     200K
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.929
_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:
 C00N(H00B,H00C), C012(H01A,H01B), C015(H01C,H01D), C018(H01E,H01F), C01B(H01H,
 H01I), C01G(H01O,H01P)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00O(H00O), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011),
 C013(H013), C016(H016), C01A(H01G), C01C(H01J), C01E(H01K), C01H(H01Q),
 C01I(H01R), C01K(H01V), C01L(H01W), C01M(H01X), C01O(H01Y), C01P(H01Z),
 C01Q(H01), C01S(H1), C01T(H2), C01U(H3)
2.c Idealised Me refined as rotating group:
 C01F(H01L,H01M,H01N), C01J(H01S,H01T,H01U), C01V(H4,H,HA), C01W(H5,HB,HC)
;
_shelx_res_checksum              8237
_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 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.723