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_7159188
_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         'C29 H30 O11 S'
_chemical_formula_sum            'C29 H30 O11 S'
_chemical_formula_weight         586.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-20
_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                90
_cell_angle_beta                 95.210(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8679(2)
_cell_length_b                   19.3858(5)
_cell_length_c                   15.9313(3)
_cell_measurement_reflns_used    21624
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9410
_cell_measurement_theta_min      2.4580
_cell_volume                     2727.46(11)
_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    '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 0.997
_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    -15.00 100.00   0.50   11.49    --   10.60  77.00 -60.00  230
  2  \w    -15.00 100.00   0.50   11.49    --   10.60  77.00 120.00  230
  3  \w    -79.00  41.00   0.50   11.49    --   10.60 -57.00 -30.00  240
  4  \w    -79.00 -40.00   0.50   11.49    --   10.60 -57.00   0.00   78
  5  \w    -17.00 100.00   0.50   11.49    --   10.60  82.00 150.00  234
  6  \w    -79.00  35.00   0.50   11.49    --   10.60 -57.00   0.00  228
  7  \w      9.00  35.00   0.50   11.49    --   10.60 -57.00   0.00   52
  8  \w    -36.00  17.00   0.50   11.49    --  -10.90 -82.00  90.00  106
  9  \w    -13.00  76.00   0.50   11.49    --  -10.90  77.00  30.00  178
;
_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      0.0386453000
_diffrn_orient_matrix_UB_12      -0.0112682000
_diffrn_orient_matrix_UB_13      -0.0346014000
_diffrn_orient_matrix_UB_21      -0.0233759000
_diffrn_orient_matrix_UB_22      -0.0343936000
_diffrn_orient_matrix_UB_23      0.0068685000
_diffrn_orient_matrix_UB_31      -0.0663712000
_diffrn_orient_matrix_UB_32      0.0055377000
_diffrn_orient_matrix_UB_33      -0.0274431000
_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  0.0369
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35913
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.045
_diffrn_reflns_theta_min         2.462
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11639
_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    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         5718
_refine_ls_number_restraints     1315
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0537P)^2^+1.8571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4845
_reflns_number_total             5718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00149k2.cif
_cod_data_source_block           k11001-myc-f
_cod_depositor_comments
'Adding full bibliography for 7159184--7159192.cif.'
_cod_database_code               7159188
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.20
_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. Rigid bond restraints
 O7, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 7.8
3. Uiso/Uaniso restraints and constraints
C9 \\sim C1 \\sim C18 \\sim C26 \\sim C7 \\sim C25 \\sim C17 \\sim C23 \\sim C8
\\sim C22 \\sim C13 \\sim C19 \\sim C2 \\sim C10 \\sim C24 \\sim C3 \\sim C27
\\sim C14 \\sim C6 \\sim C15 \\sim C16 \\sim C12 \\sim C29 \\sim C4 \\sim C21
\\sim C11 \\sim C20 \\sim C5 \\sim C28 \\sim O2 \\sim O4 \\sim O6 \\sim O9
\\sim O10 \\sim O1 \\sim O7 \\sim O11 \\sim O3 \\sim O5 \\sim O8 \\sim S1:
within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 3.8A
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C24(H24), C27(H27), C4(H4), C11(H11), C28(H28)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C16(H16A,H16B,
 H16C), C29(H29A,H29B,H29C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              67679
_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 5.625
_oxdiff_exptl_absorpt_empirical_full_min 0.573