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_7159109
_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         'C40 H38 O6 S2'
_chemical_formula_sum            'C40 H38 O6 S2'
_chemical_formula_weight         678.82
_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             2020-06-02
_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                62.701(2)
_cell_angle_beta                 86.646(2)
_cell_angle_gamma                73.3530(10)
_cell_formula_units_Z            2
_cell_length_a                   10.30720(10)
_cell_length_b                   14.2750(3)
_cell_length_c                   15.3721(4)
_cell_measurement_reflns_used    21143
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9040
_cell_measurement_theta_min      2.0700
_cell_volume                     1918.57(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.952
_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  41.00   0.50   16.92    --   10.60 -57.00  80.00  240
  2  \w    -20.00 100.00   0.50   16.92    --   10.60  57.00-137.00  240
  3  \w    -35.00  75.00   0.50   16.92    --  -10.90  57.00-137.00  220
  4  \w    -65.00 -40.00   0.50   16.92    --  -10.90 -57.00  80.00   50
  5  \w     14.00 100.00   0.50   16.92    --   10.60  77.00 -30.00  172
  6  \w    -16.00  51.00   0.50   16.92    --   10.60  82.00-120.00  134
  7  \w    -13.00  26.00   0.50   16.92    --   10.60  77.00  90.00   78
  8  \w     49.00 100.00   0.50   16.92    --   10.60  82.00 -90.00  102
  9  \w     74.00 100.00   0.50   16.92    --   10.60  77.00  90.00   52
 10  \w    -14.00  31.00   0.50   16.92    --   10.60  82.00 -60.00   90
 11  \w      0.00  26.00   0.50   16.92    --   10.60  82.00 -90.00   52
 12  \w    -17.00  30.00   0.50   16.92    --   10.60  82.00   0.00   94
 13  \w     33.00  59.00   0.50   16.92    --   10.60  82.00   0.00   52
 14  \w    -79.00  36.00   0.50   16.92    --   10.60 -77.00 120.00  230
 15  \w    -70.00  -1.00   0.50   16.92    --   10.60 -57.00-180.00  138
 16  \w     -8.00 100.00   0.50   16.92    --   10.60  82.00-180.00  216
 17  \w    -50.00 -24.00   0.50   16.92    --   10.60 -77.00-120.00   52
 18  \w    -49.00 -24.00   0.50   16.92    --   10.60 -78.00 -21.92   50
 19  \w      5.00  36.00   0.50   16.92    --   10.60 -78.00 -21.92   62
 20  \w     -7.00  46.00   0.50   16.92    --   10.60  82.00  90.00  106
 21  \w     -8.00  17.00   0.50   16.92    --  -10.90 -82.00  30.00   50
 22  \w    -99.00 -28.00   0.50   16.92    --  -10.90 -82.00  30.00  142
 23  \w    -72.00 -47.00   0.50   16.92    --  -10.90 -82.00 150.00   50
;
_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      0.0390428000
_diffrn_orient_matrix_UB_12      -0.0549510000
_diffrn_orient_matrix_UB_13      0.0310131000
_diffrn_orient_matrix_UB_21      0.0604752000
_diffrn_orient_matrix_UB_22      0.0141549000
_diffrn_orient_matrix_UB_23      -0.0171891000
_diffrn_orient_matrix_UB_31      0.0039352000
_diffrn_orient_matrix_UB_32      0.0141256000
_diffrn_orient_matrix_UB_33      0.0381950000
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43823
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.005
_diffrn_reflns_theta_min         1.654
_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  0.62082
_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    1.175
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0814P)^2^+1.7797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1681
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6369
_reflns_number_total             7990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02199d2.cif
_cod_data_source_block           k10906-myc-a
_cod_depositor_comments
'Adding full bibliography for 7159105--7159114.cif.'
_cod_original_cell_volume        1918.57(7)
_cod_database_code               7159109
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C39 H34 O6 S2'
_diffrn_oxdiff_digest_frames
;
01125918f4068438183eeeb4fca17ca32c00025aba9
;
_diffrn_oxdiff_digest_hkl
;
01d06997705bd232a012a5bc722da39187a42e
;
_reflns_odcompleteness_completeness 99.35
_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:
 C8(H8), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C21(H21), C22(H22), C28(H28), C29(H29), C31(H31), C32(H32),
  C35(H35), C36(H36), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C33(H33A,H33B,H33C), C40(H40A,H40B,
 H40C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              62776
_shelx_fab_checksum              15203
_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 1.319
_oxdiff_exptl_absorpt_empirical_full_min 0.678