One-pot synthesis of sulfonyl dibenzosuberdiones <i>via</i> In(OTf)<sub>3</sub>-promoted double Friedel-Crafts reactions of oxygenated arylacetic acids with β-arylvinyl sulfones.
Chang, Meng-Yang; Lin, Chun-Yi; Organic & biomolecular chemistry 21 (2023) 2405–2416; doi:10.1039/d3ob00149k

data_7159184
_publ_section_title
;
 One-pot synthesis of sulfonyl dibenzosuberdiones <i>via</i>
 In(OTf)<sub>3</sub>-promoted double Friedel-Crafts reactions of
 oxygenated arylacetic acids with &#x3b2;-arylvinyl sulfones.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2405
_journal_page_last               2416
_journal_paper_doi               10.1039/d3ob00149k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C27 H26 O8 S'
_chemical_formula_sum            'C27 H26 O8 S'
_chemical_formula_weight         510.54
_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     iterative
_audit_creation_date             2020-08-20
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2022-11-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                95.015(3)
_cell_angle_beta                 110.780(4)
_cell_angle_gamma                99.316(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3890(4)
_cell_length_b                   11.3607(4)
_cell_length_c                   12.5465(5)
_cell_measurement_reflns_used    12480
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.7840
_cell_measurement_theta_min      2.3260
_cell_volume                     1219.41(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.951
_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    -17.00 100.00   0.50   48.47    --   10.60  82.00  90.00  234
  2  \w    -17.00 100.00   0.50   48.47    --   10.60  82.00 -60.00  234
  3  \w    -17.00 100.00   0.50   48.47    --   10.60  82.00  60.00  234
  4  \w    -15.00 100.00   0.50   48.47    --   10.60  77.00-180.00  230
  5  \w    -15.00 100.00   0.50   48.47    --   10.60  77.00   0.00  230
  6  \w    -17.00 100.00   0.50   48.47    --   10.60  82.00 -90.00  234
  7  \w      2.00  97.00   0.50   48.47    --   10.60  38.00 -30.00  190
  8  \w    -17.00  94.00   0.50   48.47    --   10.60  82.00 150.00  222
  9  \w    -11.00  36.00   0.50   48.47    --   10.60  82.00  30.00   94
 10  \w    -17.00  96.00   0.50   48.47    --   10.60  82.00-120.00  226
 11  \w    -75.00  48.00   0.50   48.47    --   10.60 -38.00  30.00  246
 12  \w    -27.00  19.00   0.50   48.47    --  -10.90  82.00 120.00   92
 13  \w      3.00  50.00   0.50   48.47    --  -10.90   0.00  90.00   94
 14  \w    -75.00 -49.00   0.50   48.47    --  -10.90   0.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0057165000
_diffrn_orient_matrix_UB_12      0.0505138000
_diffrn_orient_matrix_UB_13      0.0398590000
_diffrn_orient_matrix_UB_21      -0.0246178000
_diffrn_orient_matrix_UB_22      0.0334944000
_diffrn_orient_matrix_UB_23      -0.0459679000
_diffrn_orient_matrix_UB_31      -0.0786313000
_diffrn_orient_matrix_UB_32      -0.0207509000
_diffrn_orient_matrix_UB_33      -0.0068467000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27691
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.045
_diffrn_reflns_theta_min         2.336
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0632P)^2^+0.8447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4084
_reflns_number_total             5083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00149k2.cif
_cod_data_source_block           k10908-myc-c
_cod_depositor_comments
'Adding full bibliography for 7159184--7159192.cif.'
_cod_database_code               7159184
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C27 H24 S O8'
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C14(H14), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              14459
_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 0.693