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_7159110
_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         'C38 H36 O6'
_chemical_formula_sum            'C38 H36 O6'
_chemical_formula_weight         588.67
_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             2020-09-03
_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                106.306(2)
_cell_angle_beta                 107.568(2)
_cell_angle_gamma                98.437(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1316(2)
_cell_length_b                   12.7947(3)
_cell_length_c                   14.4860(4)
_cell_measurement_reflns_used    19528
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.0110
_cell_measurement_theta_min      2.3590
_cell_volume                     1498.28(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 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 0.997
_diffrn_measured_fraction_theta_max 0.951
_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    -20.00 100.00   0.50   24.59    --   10.60  57.00-180.00  240
  2  \w    -79.00  41.00   0.50   24.59    --   10.60 -57.00 120.00  240
  3  \w    -79.00  36.00   0.50   24.59    --   10.60 -77.00  60.00  230
  4  \w    -15.00 100.00   0.50   24.59    --   10.60  77.00-150.00  230
  5  \w    -79.00  38.00   0.50   24.59    --   10.60 -82.00 120.00  234
  6  \w    -17.00 100.00   0.50   24.59    --   10.60  82.00   0.00  234
  7  \w    -17.00 100.00   0.50   24.59    --   10.60  82.00 -60.00  234
  8  \w    -17.00 100.00   0.50   24.59    --   10.60  82.00  60.00  234
  9  \w    -17.00 100.00   0.50   24.59    --   10.60  82.00-120.00  234
 10  \w    -17.00 100.00   0.50   24.59    --   10.60  82.00-180.00  234
 11  \w    -79.00  38.00   0.50   24.59    --   10.60 -82.00 -60.00  234
 12  \w   -100.00  17.00   0.50   24.59    --  -10.90 -82.00 -90.00  234
 13  \w   -100.00 -14.00   0.50   24.59    --  -10.90 -82.00  30.00  172
 14  \w    -17.00  16.00   0.50   24.59    --  -10.90 -82.00   0.00   66
 15  \w    -63.00 -29.00   0.50   24.59    --  -10.90 -82.00   0.00   68
;
_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      0.0778576000
_diffrn_orient_matrix_UB_12      0.0236379000
_diffrn_orient_matrix_UB_13      0.0374395000
_diffrn_orient_matrix_UB_21      0.0289407000
_diffrn_orient_matrix_UB_22      0.0064675000
_diffrn_orient_matrix_UB_23      -0.0388590000
_diffrn_orient_matrix_UB_31      -0.0138820000
_diffrn_orient_matrix_UB_32      0.0544406000
_diffrn_orient_matrix_UB_33      0.0090415000
_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  0.0695
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37071
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.050
_diffrn_reflns_theta_min         2.360
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83308
_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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.1818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4983
_reflns_number_total             6264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02199d2.cif
_cod_data_source_block           k10908-myc-e
_cod_depositor_comments
'Adding full bibliography for 7159105--7159114.cif.'
_cod_original_cell_volume        1498.27(7)
_cod_database_code               7159110
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H17 O3 Br'
_reflns_odcompleteness_completeness 99.33
_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:
 C10(H10A,H10B), C12(H12A,H12B), C19(H19A,H19B), C22(H22A,H22B), C31(H31A,
 H31B), C38(H38A,H38B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34),
  C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              74959
_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 3.554
_oxdiff_exptl_absorpt_empirical_full_min 0.759