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_7159111
_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         'C42 H36 O8 S2'
_chemical_formula_sum            'C42 H36 O8 S2'
_chemical_formula_weight         732.83
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-22
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2020-11-03 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                91.424(3)
_cell_angle_beta                 109.342(4)
_cell_angle_gamma                107.452(4)
_cell_formula_units_Z            2
_cell_length_a                   11.1955(4)
_cell_length_b                   13.5009(6)
_cell_length_c                   14.0064(6)
_cell_measurement_reflns_used    14169
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.3520
_cell_measurement_theta_min      2.0360
_cell_volume                     1887.39(15)
_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 0.996
_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    -23.00 100.00   0.50   21.52    --   10.60  49.00  52.00  246
  2  \w    -79.00  37.00   0.50   21.52    --   10.60 -49.00 -95.00  232
  3  \w      7.00  33.00   0.50   21.52    --  -10.90  49.00  52.00   52
  4  \w    -39.00 -14.00   0.50   21.52    --  -10.90 -49.00 -95.00   50
  5  \w     -7.00  43.00   0.50   21.52    --   10.60  82.00-180.00  100
  6  \w     34.00  99.00   0.50   21.52    --   10.60  57.00  90.00  130
  7  \w    -15.00  99.00   0.50   21.52    --   10.60  77.00 150.00  228
  8  \w     56.00  89.00   0.50   21.52    --   10.60  82.00-180.00   66
  9  \w    -10.00  48.00   0.50   21.52    --   10.60  82.00  90.00  116
 10  \w    -34.00  -3.00   0.50   21.52    --   10.60 -77.00 150.00   62
 11  \w      9.00  35.00   0.50   21.52    --   10.60  57.00-150.00   52
 12  \w     60.00  86.00   0.50   21.52    --   10.60  57.00-150.00   52
 13  \w      8.00  96.00   0.50   21.52    --   10.60  82.00 -60.00  176
 14  \w    -16.00  99.00   0.50   21.52    --   10.60  82.00 -90.00  230
 15  \w    -18.00   8.00   0.50   21.52    --   10.60  57.00  90.00   52
 16  \w     -8.00  60.00   0.50   21.52    --   10.60  82.00   0.00  136
 17  \w     68.00 100.00   0.50   21.52    --   10.60  82.00   0.00   64
 18  \w    -35.00  78.00   0.50   21.52    --  -10.90  64.00  50.76  226
 19  \w    -25.00   0.00   0.50   21.52    --  -10.90  77.00-150.00   50
 20  \w    -12.00  13.00   0.50   21.52    --  -10.90 -82.00 -90.00   50
 21  \w    -90.00 -43.00   0.50   21.52    --  -10.90 -82.00 -90.00   94
 22  \w    -70.00 -44.00   0.50   21.52    --  -10.90 -82.00 -30.00   52
 23  \w   -100.00 -20.00   0.50   21.52    --  -10.90 -82.00-150.00  160
;
_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      0.0300356000
_diffrn_orient_matrix_UB_12      -0.0335259000
_diffrn_orient_matrix_UB_13      0.0301617000
_diffrn_orient_matrix_UB_21      -0.0640023000
_diffrn_orient_matrix_UB_22      -0.0383311000
_diffrn_orient_matrix_UB_23      -0.0119407000
_diffrn_orient_matrix_UB_31      0.0069815000
_diffrn_orient_matrix_UB_32      -0.0223281000
_diffrn_orient_matrix_UB_33      -0.0434065000
_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  0.0753
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38013
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.596
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75448
_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    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         6626
_refine_ls_number_restraints     303
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0624P)^2^+1.5969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4732
_reflns_number_total             6626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02199d2.cif
_cod_data_source_block           k10909-myc-g
_cod_depositor_comments
'Adding full bibliography for 7159105--7159114.cif.'
_cod_database_code               7159111
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C42 H31 S2 O8'
_reflns_odcompleteness_completeness 99.22
_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
 C26-H26
 0.93 with sigma of 0.02
3. Rigid bond restraints
 O4, C25
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 9
 C25, C26
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 9.5
4. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq,
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(O1)
\\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4) \\sim Ueq,
Uanis(O5) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O8) \\sim
Ueq: with sigma of 0.008 and sigma for terminal atoms of 0.008
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C17(H17A,H17B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C21(H21), C22(H22), C23(H23), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33),
  C34(H34), C37(H37), C38(H38), C40(H40), C41(H41)
5.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C42(H42A,H42B,H42C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              79849
_shelx_fab_checksum              94295
_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 2.397
_oxdiff_exptl_absorpt_empirical_full_min 0.676