BF3·OEt2-Mediated Nucleophilic Fluorocyclization of Sulfonyl 3-Methylene-oxabenzocyclooctan-6-ones. Diastereocontrolled Synthesis of Benzofused Fluorooxabicyclo[4.2.1]nonanes
Hsueh, Nai-Chen; Chang, Meng-Yang; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01459A

data_7158875
_publ_section_title
;
 BF3&#x00B7;OEt2-Mediated Nucleophilic Fluorocyclization of Sulfonyl
 3-Methylene-oxabenzocyclooctan-6-ones. Diastereocontrolled Synthesis of
 Benzofused Fluorooxabicyclo[4.2.1]nonanes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01459A
_journal_year                    2022
_chemical_formula_moiety         'C19 H18 Cl F O3 S'
_chemical_formula_sum            'C19 H18 Cl F O3 S'
_chemical_formula_weight         380.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-02-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-11 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.409(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9529(3)
_cell_length_b                   7.52540(10)
_cell_length_c                   15.8144(3)
_cell_measurement_reflns_used    18945
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9380
_cell_measurement_theta_min      2.6480
_cell_volume                     1707.06(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 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 1.000
_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    -36.00   7.00   0.50    3.66    --   10.60 -79.00 -30.00   86
  2  \w     16.00  99.00   0.50    3.66    --   10.60  79.00  93.00  166
  3  \w    -43.00 -13.00   0.50    3.66    --  -10.90 -79.00 -30.00   60
  4  \w    -31.00  -6.00   0.50    3.66    --  -10.90  79.00  93.00   50
  5  \w     -3.00  23.00   0.50    3.66    --   10.60  82.00-180.00   52
  6  \w    -77.00 -51.00   0.50    3.66    --   10.60 -77.00   0.00   52
  7  \w     19.00 100.00   0.50    3.66    --   10.60  77.00-150.00  162
  8  \w     -9.00  37.00   0.50    3.66    --   10.60  82.00-120.00   92
  9  \w    -17.00 100.00   0.50    3.66    --   10.60  82.00 150.00  234
 10  \w     23.00  48.00   0.50    3.66    --   10.60  77.00 -90.00   50
 11  \w     19.00  91.00   0.50    3.66    --   10.60  82.00   0.00  144
 12  \w    -17.00 100.00   0.50    3.66    --   10.60  82.00  60.00  234
 13  \w    -50.00 -21.00   0.50    3.66    --  -10.90 -82.00 -90.00   58
 14  \w     54.00  79.00   0.50    3.66    --  -10.90  77.00 120.00   50
 15  \w    -33.00  -8.00   0.50    3.66    --  -10.90  57.00  60.00   50
 16  \w    -34.00  -8.00   0.50    3.66    --  -10.90  77.00 120.00   52
 17  \w    -31.00  79.00   0.50    3.66    --  -10.90  77.00  30.00  220
 18  \w    -14.00  17.00   0.50    3.66    --  -10.90 -82.00 -90.00   62
 19  \w    -33.00  53.00   0.50    3.66    --  -10.90  77.00 -60.00  172
 20  \w     22.00  72.00   0.50    3.66    --  -10.90  57.00  60.00  100
 21  \w    -50.00   8.00   0.50    3.66    --  -10.90 -77.00-150.00  116
;
_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      -0.0393438000
_diffrn_orient_matrix_UB_12      -0.0294666000
_diffrn_orient_matrix_UB_13      -0.0337832000
_diffrn_orient_matrix_UB_21      0.0298885000
_diffrn_orient_matrix_UB_22      -0.0448796000
_diffrn_orient_matrix_UB_23      -0.0206734000
_diffrn_orient_matrix_UB_31      -0.0023312000
_diffrn_orient_matrix_UB_32      -0.0773961000
_diffrn_orient_matrix_UB_33      0.0248753000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31146
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.66
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+1.1332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                3062
_reflns_number_total             3362
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob01459a2.cif
_cod_data_source_block           nco115nb
_cod_original_cell_volume        1707.06(5)
_cod_database_code               7158875
_chemical_oxdiff_formula         'C19 H18 O3 Cl1 F1 S1'
_diffrn_oxdiff_digest_frames
;
017417dda8dd145a762ff1d34b10eab0d4000253299
;
_diffrn_oxdiff_digest_hkl
;
01b0e261cff2fff9c603219d8776f85245c412
;
_reflns_odcompleteness_completeness 99.76
_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 Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.720