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_7159190
_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 H25 F O9 S, C H Cl3'
_chemical_formula_sum            'C28 H26 Cl3 F O9 S'
_chemical_formula_weight         663.90
_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             2020-12-04
_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                79.068(2)
_cell_angle_beta                 81.726(2)
_cell_angle_gamma                72.665(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4568(2)
_cell_length_b                   10.0048(2)
_cell_length_c                   18.1713(4)
_cell_measurement_reflns_used    22513
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9660
_cell_measurement_theta_min      2.1430
_cell_volume                     1434.70(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -79.00  36.00   0.50    4.48    --   10.60 -77.00  60.00  230
  2  \w    -79.00  35.00   0.50    4.48    --   10.60 -68.00 -84.22  228
  3  \w    -17.00 100.00   0.50    4.48    --   10.60  82.00 -60.00  234
  4  \w    -17.00 100.00   0.50    4.48    --   10.60  82.00 150.00  234
  5  \w    -20.00 100.00   0.50    4.48    --   10.60  57.00-120.00  240
  6  \w    -17.00 100.00   0.50    4.48    --   10.60  82.00  90.00  234
  7  \w    -79.00  36.00   0.50    4.48    --   10.60 -76.00  11.45  230
  8  \w    -15.00 100.00   0.50    4.48    --   10.60  77.00-150.00  230
  9  \w   -100.00  17.00   0.50    4.48    --  -10.90 -82.00 120.00  234
 10  \w   -100.00  17.00   0.50    4.48    --  -10.90 -82.00   0.00  234
 11  \w   -100.00  17.00   0.50    4.48    --  -10.90 -82.00-120.00  234
 12  \w   -100.00  15.00   0.50    4.48    --  -10.90 -77.00 -60.00  230
 13  \w    -79.00 -32.00   0.50    4.48    --   10.60 -77.00 120.00   94
 14  \w    -38.00  79.00   0.50    4.48    --  -10.90  82.00-180.00  234
;
_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      0.0533532000
_diffrn_orient_matrix_UB_12      -0.0658144000
_diffrn_orient_matrix_UB_13      0.0151779000
_diffrn_orient_matrix_UB_21      -0.0087703000
_diffrn_orient_matrix_UB_22      0.0244193000
_diffrn_orient_matrix_UB_23      0.0349536000
_diffrn_orient_matrix_UB_31      -0.0697445000
_diffrn_orient_matrix_UB_32      -0.0269176000
_diffrn_orient_matrix_UB_33      0.0119265000
_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  0.0464
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35403
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.159
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30426
_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    1.537
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.925
_refine_diff_density_min         -1.150
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         5016
_refine_ls_number_restraints     1380
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1107P)^2^+1.9535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.1797
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4445
_reflns_number_total             5016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00149k2.cif
_cod_data_source_block           k10912-myc-a
_cod_depositor_comments
'Adding full bibliography for 7159184--7159192.cif.'
_cod_database_code               7159190
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
019f71c277a9bb1086302060c690bd18fa000259416
;
_diffrn_oxdiff_digest_hkl
;
0181ae7013976170e5fb1cfa6ed8de7136ace7
;
_reflns_odcompleteness_completeness 99.37
_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. Restrained distances
 Cl2-C28 \\sim Cl5-C29
 with sigma of 0.02
 Cl3-C28 \\sim Cl6-C29
 with sigma of 0.02
 Cl1-C28 \\sim Cl4-C29
 with sigma of 0.02
 Cl2-Cl3 \\sim Cl5-Cl6
 with sigma of 0.04
 Cl2-Cl1 \\sim Cl5-Cl4
 with sigma of 0.04
 Cl3-Cl1 \\sim Cl6-Cl4
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim O1 \\sim O2 \\sim O3 \\sim O4
\\sim O5 \\sim O6 \\sim O7 \\sim O8 \\sim O9 \\sim S1 \\sim Cl1 \\sim Cl2 \\sim
Cl3 \\sim Cl4 \\sim Cl5 \\sim Cl6 \\sim F1: within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=Sof(C29)=Sof(H29)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C28)=Sof(H28)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C28(H28), C29(H29)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C14(H14), C23(H23), C24(H24), C26(H26), C27(H27)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              89814
_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 1.957
_oxdiff_exptl_absorpt_empirical_full_min 0.464