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_7159112
_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 H22 O4 S'
_chemical_formula_sum            'C23 H22 O4 S'
_chemical_formula_weight         394.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-05
_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                 105.952(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1182(3)
_cell_length_b                   11.9825(2)
_cell_length_c                   20.4080(4)
_cell_measurement_reflns_used    13011
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8830
_cell_measurement_theta_min      2.1470
_cell_volume                     3789.75(13)
_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 0.953
_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    -79.00 100.00   0.50   34.30    --   10.60 -19.00 -60.00  358
  2  \w    -15.00 100.00   0.50   34.30    --   10.60  77.00-180.00  230
  3  \w    -79.00  41.00   0.50   34.30    --   10.60 -57.00  60.00  240
  4  \w    -79.00  41.00   0.50   34.30    --   10.60 -57.00-180.00  240
  5  \w    -79.00  18.00   0.50   34.30    --   10.60 -77.00 -60.00  194
  6  \w    -58.00  -7.00   0.50   34.30    --  -10.90 -57.00 120.00  102
;
_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      0.0328782000
_diffrn_orient_matrix_UB_12      -0.0271401000
_diffrn_orient_matrix_UB_13      0.0253384000
_diffrn_orient_matrix_UB_21      0.0203847000
_diffrn_orient_matrix_UB_22      -0.0162721000
_diffrn_orient_matrix_UB_23      -0.0251755000
_diffrn_orient_matrix_UB_31      0.0244832000
_diffrn_orient_matrix_UB_32      0.0500183000
_diffrn_orient_matrix_UB_33      0.0055669000
_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  0.0246
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21960
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.057
_diffrn_reflns_theta_min         2.076
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66204
_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    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0678P)^2^+4.6744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3582
_reflns_number_total             3978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02199d2.cif
_cod_data_source_block           k10905-myc-a
_cod_depositor_comments
'Adding full bibliography for 7159105--7159114.cif.'
_cod_database_code               7159112
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H20 O3 S1'
_diffrn_oxdiff_digest_frames
;
0171cc723889e23743fc34b5bdc9ca803c00025efd1
;
_diffrn_oxdiff_digest_hkl
;
01ada15eb2271a878c4d2dcc5debca170dc064
;
_reflns_odcompleteness_completeness 99.51
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C15(H15C,H15A,H15B)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              25029
_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.501