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_7159191
_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     dual
_audit_creation_date             2020-09-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-11-22 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                114.802(2)
_cell_angle_beta                 99.369(2)
_cell_angle_gamma                91.662(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4581(2)
_cell_length_b                   12.4673(3)
_cell_length_c                   13.9001(3)
_cell_measurement_reflns_used    18628
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9880
_cell_measurement_theta_min      2.4480
_cell_volume                     1305.05(6)
_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 (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_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.956
_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    -20.00 100.00   0.50    9.21    --   10.60  57.00   0.00  240
  2  \w    -17.00 100.00   0.50    9.21    --   10.60  82.00 -90.00  234
  3  \w    -17.00 100.00   0.50    9.21    --   10.60  82.00  90.00  234
  4  \w    -17.00 100.00   0.50    9.21    --   10.60  82.00   0.00  234
  5  \w    -17.00 100.00   0.50    9.21    --   10.60  82.00-150.00  234
  6  \w    -17.00 100.00   0.50    9.21    --   10.60  82.00  60.00  234
  7  \w    -79.00  37.00   0.50    9.21    --   10.60 -80.00 134.87  232
  8  \w    -79.00  37.00   0.50    9.21    --   10.60 -79.00  43.16  232
  9  \w    -17.00 100.00   0.50    9.21    --   10.60  82.00-180.00  234
 10  \w    -67.00  40.00   0.50    9.21    --   10.60 -57.00  60.00  214
 11  \w    -67.00 -23.00   0.50    9.21    --   10.60 -77.00-180.00   88
 12  \w     -7.00  36.00   0.50    9.21    --   10.60 -77.00-180.00   86
 13  \w    -12.00  13.00   0.50    9.21    --  -10.90 -82.00-180.00   50
 14  \w    -77.00 -51.00   0.50    9.21    --  -10.90 -38.00  60.00   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      -0.0683198000
_diffrn_orient_matrix_UB_12      -0.0374097000
_diffrn_orient_matrix_UB_13      -0.0371262000
_diffrn_orient_matrix_UB_21      0.0485993000
_diffrn_orient_matrix_UB_22      -0.0253898000
_diffrn_orient_matrix_UB_23      -0.0392957000
_diffrn_orient_matrix_UB_31      0.0167579000
_diffrn_orient_matrix_UB_32      -0.0439403000
_diffrn_orient_matrix_UB_33      0.0189589000
_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  0.0651
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28967
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.024
_diffrn_reflns_theta_min         2.455
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76780
_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    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0637P)^2^+0.4157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4616
_reflns_number_total             5453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00149k2.cif
_cod_data_source_block           k10909-myc-d
_cod_depositor_comments
'Adding full bibliography for 7159184--7159192.cif.'
_cod_original_cell_volume        1305.04(6)
_cod_database_code               7159191
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
01b09ebd08ef877338a7c38cb5ae083bfd00025e8ef
;
_diffrn_oxdiff_digest_hkl
;
01742a89d73a2c9af63c32ebc8a35b5eea6183
;
_reflns_odcompleteness_completeness 99.40
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C11(H11), C19(H19), C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              24861
_shelx_fab_checksum              62487
_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 1.871
_oxdiff_exptl_absorpt_empirical_full_min 0.644