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_7159108
_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         'C44 H34 F2 O6 S2, 2(C H Cl3)'
_chemical_formula_sum            'C46 H36 Cl6 F2 O6 S2'
_chemical_formula_weight         999.57
_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             2020-07-07
_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                85.3580(10)
_cell_angle_beta                 75.2910(10)
_cell_angle_gamma                69.7540(10)
_cell_formula_units_Z            2
_cell_length_a                   10.35170(10)
_cell_length_b                   14.6496(2)
_cell_length_c                   16.2001(3)
_cell_measurement_reflns_used    34084
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.0560
_cell_measurement_theta_min      2.1570
_cell_volume                     2229.33(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 0.998
_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    -41.00 -16.00   0.50   32.14    --   10.60 -44.00 150.00   50
  2  \w     14.00  39.00   0.50   32.14    --   10.60  44.00 -58.00   50
  3  \w    -63.00 -38.00   0.50   32.14    --  -10.90 -44.00 150.00   50
  4  \w      8.00  36.00   0.50   32.14    --  -10.90  44.00 -58.00   56
  5  \w    -17.00  36.00   0.50   32.14    --   10.60  82.00-150.00  106
  6  \w     16.00  50.00   0.50   32.14    --   10.60  77.00-180.00   68
  7  \w      9.00  41.00   0.50   32.14    --   10.60 -57.00-120.00   64
  8  \w    -17.00 100.00   0.50   32.14    --   10.60  82.00 -30.00  234
  9  \w     22.00  76.00   0.50   32.14    --   10.60  77.00   0.00  108
 10  \w     62.00  88.00   0.50   32.14    --   10.60  82.00  60.00   52
 11  \w     12.00  38.00   0.50   32.14    --   10.60  77.00  60.00   52
 12  \w     -7.00  55.00   0.50   32.14    --   10.60  82.00  90.00  124
 13  \w     34.00 100.00   0.50   32.14    --   10.60  82.00 150.00  132
 14  \w     -8.00  23.00   0.50   32.14    --   10.60  82.00 150.00   62
 15  \w     41.00  67.00   0.50   32.14    --   10.60  82.00-150.00   52
 16  \w     13.00  39.00   0.50   32.14    --   10.60  77.00 -60.00   52
 17  \w     47.00  93.00   0.50   32.14    --   10.60  77.00 -60.00   92
 18  \w    -63.00  -7.00   0.50   32.14    --   10.60 -57.00-120.00  112
 19  \w    -17.00   8.00   0.50   32.14    --   10.60  82.00  60.00   50
 20  \w    -60.00  40.00   0.50   32.14    --   10.60 -57.00-150.00  200
 21  \w     29.00  54.00   0.50   32.14    --   10.60  82.00  60.00   50
 22  \w    -14.00  12.00   0.50   32.14    --  -10.90 -82.00   0.00   52
 23  \w    -69.00 -44.00   0.50   32.14    --  -10.90 -82.00   0.00   50
 24  \w    -97.00 -72.00   0.50   32.14    --  -10.90 -82.00   0.00   50
 25  \w    -32.00  70.00   0.50   32.14    --  -10.90  82.00  30.00  204
 26  \w    -31.00  -5.00   0.50   32.14    --  -10.90 -57.00 120.00   52
 27  \w    -96.00 -65.00   0.50   32.14    --  -10.90 -57.00 120.00   62
 28  \w    -21.00   4.00   0.50   32.14    --  -10.90 -82.00 120.00   50
 29  \w    -26.00   2.00   0.50   32.14    --  -10.90 -82.00-120.00   56
 30  \w    -82.00 -57.00   0.50   32.14    --  -10.90 -82.00-120.00   50
 31  \w    -93.00  10.00   0.50   32.14    --  -10.90 -82.00 150.00  206
 32  \w   -100.00 -44.00   0.50   32.14    --  -10.90 -82.00 120.00  112
 33  \w    -33.00  -8.00   0.50   32.14    --  -10.90 -77.00  60.00   50
 34  \w     37.00  62.00   0.50   32.14    --  -10.90  44.00 -58.00   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      -0.0700793000
_diffrn_orient_matrix_UB_12      0.0198066000
_diffrn_orient_matrix_UB_13      -0.0057186000
_diffrn_orient_matrix_UB_21      -0.0241403000
_diffrn_orient_matrix_UB_22      0.0201868000
_diffrn_orient_matrix_UB_23      0.0417655000
_diffrn_orient_matrix_UB_31      0.0130611000
_diffrn_orient_matrix_UB_32      0.0431694000
_diffrn_orient_matrix_UB_33      -0.0164949000
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            55235
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.053
_diffrn_reflns_theta_min         1.963
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61328
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.834
_refine_diff_density_min         -1.293
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         9369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0662P)^2^+3.3466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8524
_reflns_number_total             9369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02199d2.cif
_cod_data_source_block           k10907-myc-a
_cod_depositor_comments
'Adding full bibliography for 7159105--7159114.cif.'
_cod_database_code               7159108
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C42 H33 O6 F2'
_diffrn_oxdiff_digest_frames
;
01cd7ac0a7015f3f96495c27a20c2cf580000252835
;
_diffrn_oxdiff_digest_hkl
;
0108ad029b16df6010be6f4842114e92302ab6
;
_reflns_odcompleteness_completeness 99.48
_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
2.a Ternary CH refined with riding coordinates:
 C45(H45), C46(H46)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C23(H23A,H23B), C30(H30A,H30B)
2.c 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), C25(H25), C26(H26), C27(H27),
  C28(H28), C33(H33), C34(H34), C36(H36), C37(H37), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              74813
_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 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.739