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_7159107
_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         'C29 H24 O3 S'
_chemical_formula_sum            'C29 H24 O3 S'
_chemical_formula_weight         452.54
_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             2020-10-19
_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                113.403(2)
_cell_angle_beta                 103.061(2)
_cell_angle_gamma                99.138(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6718(3)
_cell_length_b                   10.5127(2)
_cell_length_c                   12.8470(3)
_cell_measurement_reflns_used    19957
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.7830
_cell_measurement_theta_min      2.1280
_cell_volume                     1121.72(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 0.998
_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  45.00   0.50    2.92    --   10.60 -44.00  22.00  248
  2  \w    -24.00 100.00   0.50    2.92    --   10.60  44.00 173.00  248
  3  \w   -100.00  23.00   0.50    2.92    --  -10.90 -44.00  22.00  246
  4  \w    -45.00  78.00   0.50    2.92    --  -10.90  44.00 173.00  246
  5  \w    -17.00 100.00   0.50    2.92    --   10.60  82.00 -60.00  234
  6  \w    -15.00 100.00   0.50    2.92    --   10.60  77.00-150.00  230
  7  \w    -15.00 100.00   0.50    2.92    --   10.60  77.00 -90.00  230
  8  \w    -17.00 100.00   0.50    2.92    --   10.60  82.00 120.00  234
  9  \w    -17.00 100.00   0.50    2.92    --   10.60  82.00-150.00  234
 10  \w    -27.00 100.00   0.50    2.92    --   10.60  38.00-120.00  254
 11  \w   -100.00  17.00   0.50    2.92    --  -10.90 -82.00  30.00  234
 12  \w   -100.00  17.00   0.50    2.92    --  -10.90 -82.00 120.00  234
 13  \w   -100.00  17.00   0.50    2.92    --  -10.90 -82.00 -30.00  234
 14  \w   -100.00   3.00   0.50    2.92    --  -10.90 -57.00   0.00  206
 15  \w     -9.00  16.00   0.50    2.92    --  -10.90 -82.00 -90.00   50
 16  \w    -98.00 -60.00   0.50    2.92    --  -10.90 -82.00 -90.00   76
 17  \w     33.00  78.00   0.50    2.92    --  -10.90  82.00 -90.00   90
 18  \w    -36.00  16.00   0.50    2.92    --  -10.90  82.00 -90.00  104
;
_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      -0.0718366000
_diffrn_orient_matrix_UB_12      -0.0022286000
_diffrn_orient_matrix_UB_13      0.0049151000
_diffrn_orient_matrix_UB_21      -0.0221227000
_diffrn_orient_matrix_UB_22      -0.0760941000
_diffrn_orient_matrix_UB_23      -0.0344162000
_diffrn_orient_matrix_UB_31      0.0221964000
_diffrn_orient_matrix_UB_32      -0.0079118000
_diffrn_orient_matrix_UB_33      0.0531109000
_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  0.0599
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.132
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12672
_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    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0492P)^2^+0.4169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3584
_reflns_number_total             3958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02199d2.cif
_cod_data_source_block           k10910-myc-c
_cod_depositor_comments
'Adding full bibliography for 7159105--7159114.cif.'
_cod_original_cell_volume        1121.72(5)
_cod_database_code               7159107
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
01ddb39772ffe15e3c72ea0000a4af635c00025c068
;
_diffrn_oxdiff_digest_hkl
;
017bb31da4400700a58a93f8dcd6eaeb5b025a
;
_reflns_odcompleteness_completeness 99.30
_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:
 C3(H3A,H3B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27),
  C28(H28)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_shelx_res_checksum              86759
_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 4.035
_oxdiff_exptl_absorpt_empirical_full_min 0.593