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_7159918
_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_absolute_configuration unk
_chemical_formula_moiety         'C28 H18 Cl F O3 S'
_chemical_formula_sum            'C28 H18 Cl F O3 S'
_chemical_formula_weight         488.970
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_Int_Tables_number      29
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5567(2)
_cell_length_b                   11.19093(14)
_cell_length_c                   9.50595(12)
_cell_measurement_reflns_used    11577
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.1620
_cell_measurement_theta_min      3.9350
_cell_volume                     2186.83(4)
_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  'olex2.refine 1.3 (Bourhis et al., 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 0.9967
_diffrn_measured_fraction_theta_max 0.9907
_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    -48.00  26.00   0.50    0.20    --  -41.33  43.00 -90.00  148
  2  \w    -47.00 -15.00   0.50    0.40    --  -82.50  42.00-150.00   64
  3  \w    -48.00  26.00   0.50    0.20    --  -41.33  43.00   0.00  148
  4  \w    -24.00  35.00   0.50    0.20    --  -41.33  10.00 146.00  118
  5  \w     18.00 109.00   0.50    0.20    --   41.33  65.00 120.00  182
  6  \w     56.00 173.00   0.50    0.40    --   96.67  10.00 146.00  234
  7  \w      1.00 118.00   0.50    0.20    --   41.33  10.00 146.00  234
  8  \w     30.00 109.00   0.50    0.40    --   96.67-117.00  90.00  158
  9  \w     34.00  93.00   0.50    0.20    --   41.33-126.00 145.00  118
 10  \w     48.00 110.00   0.50    0.20    --   41.33-152.00  73.00  124
 11  \w     30.00 109.00   0.50    0.40    --   96.67-117.00  60.00  158
 12  \w     45.00 128.00   0.50    0.40    --   96.67-146.00 -21.00  166
 13  \w     32.00 110.00   0.50    0.40    --   96.67-122.00-126.00  156
 14  \w    -35.00  24.00   0.50    0.20    --   41.33 -10.00 -27.00  118
 15  \w    -34.00  24.00   0.50    0.20    --   41.33 -11.00-150.00  116
 16  \w     29.00  68.00   0.50    0.40    --   96.67 -59.00-150.00   78
 17  \w     30.00  57.00   0.50    0.40    --   96.67 -50.00   0.00   54
 18  \w     30.00  57.00   0.50    0.40    --   96.67 -50.00  30.00   54
 19  \w     29.00  68.00   0.50    0.40    --   96.67 -59.00  60.00   78
 20  \w     99.00 164.00   0.50    0.40    --   96.67 117.00-180.00  130
 21  \w     94.00 163.00   0.50    0.40    --   96.67 126.00-137.00  138
 22  \w     76.00 165.00   0.50    0.40    --   96.67 152.00 115.00  178
 23  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00-120.00  192
 24  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00 -90.00  192
 25  \w   -109.00 -18.00   0.50    0.20    --  -41.33 -65.00 -30.00  182
 26  \w   -109.00 -18.00   0.50    0.20    --  -41.33 -65.00-180.00  182
 27  \w    -87.00 -12.00   0.50    0.20    --  -41.33 126.00-137.00  150
 28  \w    -88.00 -16.00   0.50    0.40    --  -82.50 126.00-137.00  144
 29  \w   -118.00  -4.00   0.50    0.20    --  -41.33 -10.00 -27.00  228
 30  \w   -159.00 -45.00   0.50    0.40    --  -82.50 -10.00 -27.00  228
 31  \w   -110.00 -58.00   0.50    0.20    --  -41.33-146.00 -21.00  104
 32  \w   -109.00 -54.00   0.50    0.20    --  -41.33-152.00  73.00  110
;
_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      -0.0049496000
_diffrn_orient_matrix_UB_12      0.1370630000
_diffrn_orient_matrix_UB_13      -0.0119022000
_diffrn_orient_matrix_UB_21      -0.0083555000
_diffrn_orient_matrix_UB_22      0.0090352000
_diffrn_orient_matrix_UB_23      0.1606203000
_diffrn_orient_matrix_UB_31      0.0743084000
_diffrn_orient_matrix_UB_32      0.0101940000
_diffrn_orient_matrix_UB_33      0.0172080000
_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  0.0598
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.9967
_diffrn_reflns_Laue_measured_fraction_max 0.9907
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16231
_diffrn_reflns_point_group_measured_fraction_full 0.8901
_diffrn_reflns_point_group_measured_fraction_max 0.8829
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         68.30
_diffrn_reflns_theta_min         3.95
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62515
_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    1.485
_exptl_crystal_F_000             1013.889
_refine_diff_density_max         0.4402
_refine_diff_density_min         -0.3777
_refine_diff_density_rms         0.0587
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.038(15)
_refine_ls_d_res_high            0.8297
_refine_ls_d_res_low             11.1909
_refine_ls_extinction_coef       0.0005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0452
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0452
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+0.6492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.760
_reflns_limit_h_max              24
_reflns_limit_h_min              -24
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                3441
_reflns_number_total             3551
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ob02010j2.cif
_cod_data_source_block           SJ-B_auto
_cod_depositor_comments
'Adding full bibliography for 7159918--7159919.cif.'
_cod_original_sg_symbol_Hall     ' P 2c -2ac'
_cod_database_code               7159918
_chemical_oxdiff_formula         'C H O S F Cl'
_chemical_oxdiff_usercomment     '100 K'
_reflns_odcompleteness_completeness 90.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C32(H32), C4(H4), C15(H15), C34(H34), C33(H33), C11(H11), C22(H22),
 C6(H6), C30(H30), C20(H20), C12(H12), C31(H31), C23(H23), C3(H3)
2.b Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c)
;
_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 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.691