BF<sub>3</sub>·Et<sub>2</sub>O-assisted synthesis of sulfinylated spiro[5.5]trienones from biaryl ynones.
Roy, Barnali; Kuila, Puspendu; Jha, Sangam; Sarkar, Debayan; Organic & biomolecular chemistry 22 (2024) 4292–4296; doi:10.1039/d3ob02010j

data_7159919
_publ_section_title
;
 BF<sub>3</sub>&#xb7;Et<sub>2</sub>O-assisted synthesis of sulfinylated
 spiro[5.5]trienones from biaryl ynones.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4292
_journal_page_last               4296
_journal_paper_doi               10.1039/d3ob02010j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C27 H17 F O3 S'
_chemical_formula_sum            'C27 H17 F O3 S'
_chemical_formula_weight         440.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-12-13 deposited with the CCDC.	2024-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.4241(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.85251(18)
_cell_length_b                   9.76803(17)
_cell_length_c                   20.3019(3)
_cell_measurement_reflns_used    13869
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.8010
_cell_measurement_theta_min      4.1250
_cell_volume                     2123.11(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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    -72.00  31.00   0.50    0.25    --  -40.33  90.00 104.00  206
  2  \w    -21.00  72.00   0.50    0.25    --   40.33 -90.00 -10.00  186
  3  \w    -81.00 -11.00   0.50    1.00    --  -82.50  90.00 104.00  140
  4  \w    100.00 168.00   0.50    1.00    --   96.67  90.00 104.00  136
  5  \w     26.00 106.00   0.50    1.00    --   96.67 -90.00 -10.00  160
  6  \w    -24.00  35.00   0.50    0.25    --  -40.33  12.00  30.00  118
  7  \w    -78.00   4.00   0.50    0.25    --  -40.33 104.00   0.00  164
  8  \w    -24.00  35.00   0.50    0.25    --  -40.33  12.00 -90.00  118
  9  \w    -31.00  30.00   0.50    0.25    --  -40.33  25.00 150.00  122
 10  \w    -24.00  35.00   0.50    0.25    --  -40.33  12.00   0.00  118
 11  \w    -24.00  35.00   0.50    0.25    --  -40.33  12.00-120.00  118
 12  \w     41.00  99.00   0.50    0.25    --   40.33-138.00  30.00  116
 13  \w    -30.00  31.00   0.50    0.25    --   40.33 -25.00   0.00  122
 14  \w    -47.00 -15.00   0.50    1.00    --  -82.50  42.00-120.00   64
 15  \w   -153.00 -78.00   0.50    1.00    --  -82.50 -90.00 -10.00  150
 16  \w    -83.00 -14.00   0.50    1.00    --  -82.50  68.00 -60.00  138
 17  \w     22.00 106.00   0.50    1.00    --   96.67 -96.00  60.00  168
 18  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00-180.00   54
 19  \w     29.00  83.00   0.50    1.00    --   96.67 -68.00 -90.00  108
 20  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00  90.00   54
 21  \w     73.00 165.00   0.50    1.00    --   96.67  68.00  30.00  184
 22  \w     73.00 165.00   0.50    1.00    --   96.67  68.00 150.00  184
 23  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00  60.00   54
 24  \w     78.00 163.00   0.50    1.00    --   96.67  50.00-150.00  170
 25  \w    105.00 170.00   0.50    1.00    --   96.67  96.00 120.00  130
 26  \w     99.00 164.00   0.50    1.00    --   96.67 117.00  30.00  130
 27  \w     29.00  83.00   0.50    1.00    --   96.67 -68.00  60.00  108
 28  \w     29.00  68.00   0.50    1.00    --   96.67 -59.00  60.00   78
 29  \w     29.00  68.00   0.50    1.00    --   96.67 -59.00 120.00   78
 30  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00-150.00   54
 31  \w     82.00 167.00   0.50    1.00    --   96.67  25.00-180.00  170
 32  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00   0.00   54
 33  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00 150.00   54
 34  \w     29.00  68.00   0.50    1.00    --   96.67 -59.00   0.00   78
 35  \w     30.00 109.00   0.50    1.00    --   96.67-117.00-150.00  158
 36  \w   -107.00 -21.00   0.50    0.25    --  -40.33 -50.00 -90.00  172
 37  \w   -108.00 -17.00   0.50    0.25    --  -40.33 -64.00-150.00  182
 38  \w   -109.00 -13.00   0.50    0.25    --  -40.33 -77.00 120.00  192
 39  \w   -109.00 -13.00   0.50    0.25    --  -40.33 -77.00  90.00  192
 40  \w   -109.00 -13.00   0.50    0.25    --  -40.33 -77.00-180.00  192
 41  \w   -108.00 -17.00   0.50    0.25    --  -40.33 -64.00   0.00  182
 42  \w   -109.00 -13.00   0.50    0.25    --  -40.33 -77.00 -90.00  192
 43  \w     14.00 109.00   0.50    0.25    --   40.33  77.00 -30.00  190
 44  \w     14.00 109.00   0.50    0.25    --   40.33  77.00  30.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0956350000
_diffrn_orient_matrix_UB_12      0.0984886000
_diffrn_orient_matrix_UB_13      0.0227177000
_diffrn_orient_matrix_UB_21      0.0249191000
_diffrn_orient_matrix_UB_22      0.1045339000
_diffrn_orient_matrix_UB_23      -0.0531968000
_diffrn_orient_matrix_UB_31      -0.1045449000
_diffrn_orient_matrix_UB_32      -0.0651344000
_diffrn_orient_matrix_UB_33      -0.0507273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21307
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.208
_diffrn_reflns_theta_min         4.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             912
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0587
_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^)+(0.1039P)^2^+1.2083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3375
_reflns_number_total             3859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02010j2.cif
_cod_data_source_block           sj-c_auto
_cod_depositor_comments
'Adding full bibliography for 7159918--7159919.cif.'
_cod_database_code               7159919
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O S F'
_chemical_oxdiff_usercomment     '100 K'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C6(H6), C8(H8), C15(H15), C9(H9), C32(H32), C14(H14), C12(H12),
 C18(H18), C21(H21), C19(H19), C22(H22), C31(H31), C7(H7), C30(H30), C28(H28),
 C29(H29)
;
_shelx_res_checksum              52945
_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 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.793