Tandem <i>C</i>- and <i>O</i>-alkylative annulation of β-ketosulfones with 1,2-bisbromomethyl arenes: one-pot construction of sulfonyl indanes and dioxadibenzofused macrocycles.
Hsueh, Nai-Chen; Chen, Kuan-Ting; Chang, Meng-Yang; Organic & biomolecular chemistry 21 (2023) 1487–1500; doi:10.1039/d2ob02199d

data_7159106
_publ_section_title
;
 Tandem <i>C</i>- and <i>O</i>-alkylative annulation of
 &#x3b2;-ketosulfones with 1,2-bisbromomethyl arenes: one-pot construction
 of sulfonyl indanes and dioxadibenzofused macrocycles.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1487
_journal_page_last               1500
_journal_paper_doi               10.1039/d2ob02199d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C46 H40 O6 S2'
_chemical_formula_sum            'C46 H40 O6 S2'
_chemical_formula_weight         752.90
_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             2020-05-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-11-03 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                113.228(2)
_cell_angle_beta                 99.000(2)
_cell_angle_gamma                97.420(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7982(3)
_cell_length_b                   13.2829(4)
_cell_length_c                   16.3495(4)
_cell_measurement_reflns_used    36569
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9390
_cell_measurement_theta_min      2.1400
_cell_volume                     1888.14(10)
_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 0.997
_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    -79.00 100.00   0.50    8.13    --   10.60  19.00-150.00  358
  2  \w    -79.00  38.00   0.50    8.13    --   10.60 -82.00-180.00  234
  3  \w    -17.00 100.00   0.50    8.13    --   10.60  82.00-120.00  234
  4  \w    -15.00 100.00   0.50    8.13    --   10.60  77.00  60.00  230
  5  \w    -17.00 100.00   0.50    8.13    --   10.60  82.00  90.00  234
  6  \w    -79.00  41.00   0.50    8.13    --   10.60 -57.00-120.00  240
  7  \w    -17.00 100.00   0.50    8.13    --   10.60  82.00 150.00  234
  8  \w    -17.00 100.00   0.50    8.13    --   10.60  82.00 -90.00  234
  9  \w    -20.00 100.00   0.50    8.13    --   10.60  57.00   0.00  240
 10  \w    -20.00 100.00   0.50    8.13    --   10.60  57.00  90.00  240
 11  \w    -79.00 100.00   0.50    8.13    --   10.60  19.00-150.00  358
 12  \w    -41.00  79.00   0.50    8.13    --  -10.90  57.00  30.00  240
 13  \w   -100.00  17.00   0.50    8.13    --  -10.90 -82.00-120.00  234
 14  \w    -38.00   4.00   0.50    8.13    --  -10.90  82.00 -60.00   84
 15  \w    -38.00  79.00   0.50    8.13    --  -10.90  82.00  90.00  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      -0.0366381000
_diffrn_orient_matrix_UB_12      0.0433932000
_diffrn_orient_matrix_UB_13      0.0186445000
_diffrn_orient_matrix_UB_21      -0.0308753000
_diffrn_orient_matrix_UB_22      -0.0071716000
_diffrn_orient_matrix_UB_23      -0.0446971000
_diffrn_orient_matrix_UB_31      -0.0576608000
_diffrn_orient_matrix_UB_32      -0.0399820000
_diffrn_orient_matrix_UB_33      -0.0022579000
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            59934
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.079
_diffrn_reflns_theta_min         2.153
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54829
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0016(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         7935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.9069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6922
_reflns_number_total             7935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02199d2.cif
_cod_data_source_block           k10905-myc-b
_cod_depositor_comments
'Adding full bibliography for 7159105--7159114.cif.'
_cod_database_code               7159106
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H19 S1 O3'
_diffrn_oxdiff_digest_frames
;
01027885f1b5d1ce246cef4a29a81886970002575e2
;
_diffrn_oxdiff_digest_hkl
;
015fee47cfdb8061ff183af62b6a47eccb7ba3
;
_reflns_odcompleteness_completeness 99.50
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C24(H24A,H24B), C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28),
  C29(H29), C34(H34), C35(H35), C37(H37), C38(H38), C42(H42), C43(H43),
 C44(H44), C45(H45), C46(H46)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C39(H39A,H39B,H39C)
;
_shelx_res_checksum              44121
_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.665