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_7159105
_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         'C23 H20 O3 S'
_chemical_formula_sum            'C23 H20 O3 S'
_chemical_formula_weight         376.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-24
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   11.76610(10)
_cell_length_c                   19.6971(2)
_cell_measurement_reflns_used    45226
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9910
_cell_measurement_theta_min      2.1540
_cell_volume                     3694.52(7)
_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 1.000
_diffrn_measured_fraction_theta_max 0.980
_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      5.00  53.00   0.50   11.09    --   10.60  36.00-165.00   96
  2  \w    -70.00 -44.00   0.50   11.09    --   10.60 -36.00  37.00   52
  3  \w     14.00  39.00   0.50   11.09    --  -10.90  36.00-165.00   50
  4  \w    -61.00 -36.00   0.50   11.09    --  -10.90 -36.00  37.00   50
  5  \w     -5.00  35.00   0.50   11.09    --   10.60  82.00 -60.00   80
  6  \w    -33.00  -1.00   0.50   11.09    --   10.60 -57.00 -60.00   64
  7  \w      0.00  26.00   0.50   11.09    --   10.60  82.00-120.00   52
  8  \w     16.00  41.00   0.50   11.09    --   10.60 -57.00 -60.00   50
  9  \w    -14.00  11.00   0.50   11.09    --   10.60  82.00  30.00   50
 10  \w    -14.00 100.00   0.50   11.09    --   10.60  82.00 150.00  228
 11  \w    -14.00  97.00   0.50   11.09    --   10.60  82.00  90.00  222
 12  \w     45.00  91.00   0.50   11.09    --   10.60  82.00-120.00   92
 13  \w     62.00  88.00   0.50   11.09    --   10.60  82.00 -60.00   52
 14  \w    -17.00 100.00   0.50   11.09    --   10.60  57.00-120.00  234
 15  \w    -50.00 -13.00   0.50   11.09    --   10.60 -77.00-150.00   74
 16  \w     -4.00 100.00   0.50   11.09    --   10.60  57.00 -30.00  208
 17  \w     -7.00  40.00   0.50   11.09    --   10.60  82.00-150.00   94
 18  \w     16.00  83.00   0.50   11.09    --   10.60  82.00  30.00  134
 19  \w     27.00  53.00   0.50   11.09    --   10.60  77.00  60.00   52
 20  \w     54.00  97.00   0.50   11.09    --   10.60  77.00  60.00   86
 21  \w    -97.00  12.00   0.50   11.09    --  -10.90 -82.00-150.00  218
 22  \w    -21.00   4.00   0.50   11.09    --  -10.90 -82.00  30.00   50
 23  \w    -73.00 -48.00   0.50   11.09    --  -10.90 -82.00  30.00   50
 24  \w    -28.00   9.00   0.50   11.09    --  -10.90 -82.00 -30.00   74
 25  \w    -69.00 -43.00   0.50   11.09    --  -10.90 -82.00 -30.00   52
;
_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      -0.0430561000
_diffrn_orient_matrix_UB_12      -0.0093250000
_diffrn_orient_matrix_UB_13      -0.0071809000
_diffrn_orient_matrix_UB_21      -0.0100440000
_diffrn_orient_matrix_UB_22      0.0532595000
_diffrn_orient_matrix_UB_23      0.0147718000
_diffrn_orient_matrix_UB_31      0.0050318000
_diffrn_orient_matrix_UB_32      0.0266428000
_diffrn_orient_matrix_UB_33      -0.0320478000
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            73544
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.058
_diffrn_reflns_theta_min         2.068
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73551
_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    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0012(2)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0380P)^2^+2.0008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0823
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3623
_reflns_number_total             3978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02199d2.cif
_cod_data_source_block           k10904-myc-a
_cod_depositor_comments
'Adding full bibliography for 7159105--7159114.cif.'
_cod_database_code               7159105
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H20 O3 S1'
_diffrn_oxdiff_digest_frames
;
012e5d2c132879a120621bf29690a1a452000256284
;
_diffrn_oxdiff_digest_hkl
;
010f16ea9fa3be386c132b7bb05a6d7e58ea5d
;
_reflns_odcompleteness_completeness 99.95
_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:
 C9(H9A,H9B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              14190
_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 1.144
_oxdiff_exptl_absorpt_empirical_full_min 0.825