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_7159114
_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         'C48 H44 O6 S2'
_chemical_formula_sum            'C48 H44 O6 S2'
_chemical_formula_weight         780.99
_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             2020-06-04
_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                85.246(2)
_cell_angle_beta                 87.858(2)
_cell_angle_gamma                74.443(2)
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_cell_length_a                   14.1278(3)
_cell_length_b                   16.6555(3)
_cell_length_c                   17.1139(3)
_cell_measurement_reflns_used    26301
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.0060
_cell_measurement_theta_min      2.3780
_cell_volume                     3865.64(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 0.995
_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    -57.00 -24.00   0.50   32.08    --   10.60   9.00 -68.00   66
  2  \w     14.00  50.00   0.50   32.08    --  -10.90   9.00 -68.00   72
  3  \w    -35.00 -10.00   0.50   32.08    --  -10.90  -9.00 118.00   50
  4  \w    -25.00   0.00   0.50   32.08    --  -10.90   9.00 -68.00   50
  5  \w     -5.00  21.00   0.50   32.08    --   10.60  82.00  60.00   52
  6  \w     -5.00  31.00   0.50   32.08    --   10.60  82.00  30.00   72
  7  \w     20.00 100.00   0.50   32.08    --   10.60  77.00 -90.00  160
  8  \w     -2.00  47.00   0.50   32.08    --   10.60  82.00-120.00   98
  9  \w     51.00 100.00   0.50   32.08    --   10.60  77.00  90.00   98
 10  \w     -7.00  19.00   0.50   32.08    --   10.60  77.00  90.00   52
 11  \w    -16.00  45.00   0.50   32.08    --   10.60  82.00   0.00  122
 12  \w    -14.00  11.00   0.50   32.08    --   10.60  -9.00 118.00   50
 13  \w    -15.00 100.00   0.50   32.08    --   10.60  82.00 150.00  230
 14  \w    -16.00   9.00   0.50   32.08    --   10.60  57.00   0.00   50
 15  \w     13.00  94.00   0.50   32.08    --   10.60  57.00   0.00  162
 16  \w     -3.00  42.00   0.50   32.08    --   10.60  82.00-180.00   90
 17  \w    -29.00  36.00   0.50   32.08    --   10.60 -77.00  60.00  130
 18  \w    -78.00  27.00   0.50   32.08    --   10.60 -82.00-120.00  210
 19  \w    -92.00  16.00   0.50   32.08    --  -10.90 -57.00  60.00  216
 20  \w    -45.00  12.00   0.50   32.08    --  -10.90 -82.00-180.00  114
 21  \w    -25.00  11.00   0.50   32.08    --  -10.90 -82.00 -30.00   72
 22  \w    -98.00 -44.00   0.50   32.08    --  -10.90 -82.00  90.00  108
 23  \w    -31.00   8.00   0.50   32.08    --  -10.90 -77.00-150.00   78
 24  \w    -91.00 -54.00   0.50   32.08    --  -10.90 -77.00-150.00   74
 25  \w    -22.00   9.00   0.50   32.08    --  -10.90 -82.00  90.00   62
;
_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      -0.0125196000
_diffrn_orient_matrix_UB_12      -0.0386386000
_diffrn_orient_matrix_UB_13      0.0043512000
_diffrn_orient_matrix_UB_21      0.0505644000
_diffrn_orient_matrix_UB_22      -0.0216729000
_diffrn_orient_matrix_UB_23      0.0018552000
_diffrn_orient_matrix_UB_31      -0.0017798000
_diffrn_orient_matrix_UB_32      0.0016646000
_diffrn_orient_matrix_UB_33      0.0413243000
_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  0.0484
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            84580
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.072
_diffrn_reflns_theta_min         1.996
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14206
_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    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.173
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1017
_refine_ls_number_reflns         16148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0913P)^2^+1.3475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12257
_reflns_number_total             16148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02199d2.cif
_cod_data_source_block           k10906-myc-e
_cod_depositor_comments
;
Adding full bibliography for 7159105--7159114.cif.

2025-01-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11.29 H10.35 O1.41 S0.47'
_cod_original_formula_weight         183.75
_cod_original_formula_moiety         '0.24(C48 H44 O6 S2)'
_cod_original_formula_units_Z            17
_cod_database_code               7159114
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
0103b983f9340122ea034fa27b8441d652000254c48
;
_diffrn_oxdiff_digest_hkl
;
0136f10d0ad3ae045de8c5cba7b05d253820fc
;
_reflns_odcompleteness_completeness 99.31
_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:
 C1(H1A,H1B), C8(H8A,H8B), C25(H25A,H25B), C32(H32A,H32B), C49(H49A,H49B),
 C56(H56A,H56B), C73(H73A,H73B), C80(H80A,H80B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15),
 C19(H19), C20(H20), C22(H22), C23(H23), C27(H27), C28(H28), C29(H29), C30(H30),
  C35(H35), C36(H36), C38(H38), C39(H39), C43(H43), C44(H44), C46(H46),
 C47(H47), C51(H51), C52(H52), C53(H53), C54(H54), C59(H59), C60(H60), C62(H62),
  C63(H63), C67(H67), C68(H68), C70(H70), C71(H71), C75(H75), C76(H76),
 C77(H77), C78(H78), C83(H83), C84(H84), C86(H86), C87(H87), C91(H91), C92(H92),
  C94(H94), C95(H95)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C40(H40A,H40B,H40C), C48(H48A,H48B,
 H48C), C64(H64A,H64B,H64C), C72(H72A,H72B,H72C), C88(H88A,H88B,H88C), C96(H96A,
 H96B,H96C)
;
_shelx_res_checksum              92344
_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 6.623
_oxdiff_exptl_absorpt_empirical_full_min 0.543