#------------------------------------------------------------------------------
#$Date: 2022-09-09 03:34:46 +0300 (Fri, 09 Sep 2022) $
#$Revision: 277744 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158871.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158871
loop_
_publ_author_name
'Hsueh, Nai-Chen'
'Chang, Meng-Yang'
_publ_section_title
;
 BF3·OEt2-Mediated Nucleophilic Fluorocyclization of Sulfonyl
 3-Methylene-oxabenzocyclooctan-6-ones. Diastereocontrolled Synthesis of
 Benzofused Fluorooxabicyclo[4.2.1]nonanes
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01459A
_journal_year                    2022
_chemical_formula_moiety         'C13 H16 O4 S'
_chemical_formula_sum            'C13 H16 O4 S'
_chemical_formula_weight         268.32
_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   mixed
_audit_creation_date             2019-12-12
_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
_cell_angle_beta                 92.806(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1912(3)
_cell_length_b                   6.0583(2)
_cell_length_c                   25.2332(11)
_cell_measurement_reflns_used    5612
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.7240
_cell_measurement_theta_min      2.5760
_cell_volume                     1250.69(8)
_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    '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 0.983
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  -4.00   0.50    5.69    --   10.60 -73.00-114.00   52
  2  ω     31.00  57.00   0.50    5.69    --   10.60  73.00  14.00   52
  3  ω    -12.00  14.00   0.50    5.69    --  -10.90  73.00  14.00   52
  4  ω    -68.00 -43.00   0.50    5.69    --  -10.90 -73.00-114.00   50
  5  ω    -14.00  12.00   0.50    5.69    --   10.60  77.00 -30.00   52
  6  ω    -15.00 100.00   0.50    5.69    --   10.60  77.00 -60.00  230
  7  ω    -55.00  37.00   0.50    5.69    --   10.60 -57.00-180.00  184
  8  ω     -6.00  90.00   0.50    5.69    --   10.60  77.00  30.00  192
  9  ω   -100.00 -38.00   0.50    5.69    --  -10.90 -82.00 150.00  124
 10  ω    -32.00  -2.00   0.50    5.69    --  -10.90 -82.00 150.00   60
 11  ω     -7.00  18.00   0.50    5.69    --  -10.90  77.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0503405000
_diffrn_orient_matrix_UB_12      0.0608727000
_diffrn_orient_matrix_UB_13      0.0167882000
_diffrn_orient_matrix_UB_21      -0.0659755000
_diffrn_orient_matrix_UB_22      -0.0726745000
_diffrn_orient_matrix_UB_23      -0.0063936000
_diffrn_orient_matrix_UB_31      0.0250842000
_diffrn_orient_matrix_UB_32      -0.0686492000
_diffrn_orient_matrix_UB_33      0.0216754000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10768
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.034
_diffrn_reflns_theta_min         2.580
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47989
_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    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.228
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0854
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+12.5635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2230
_reflns_number_total             2550
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01459a2.cif
_cod_data_source_block           ncmsn19
_cod_database_code               7158871
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C13 H16 O4 S1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_oxdiff_digest_frames
;
01f71fb24bc7f4c6e6d79c471d793301580002509e5
;
_diffrn_oxdiff_digest_hkl
;
015c616415bcaa2cc1ccaa31f44234f15fbf3b
;
_reflns_odcompleteness_completeness 99.36
_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, All O(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)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.506
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22592(15) 0.0852(2) 0.55569(5) 0.0131(3) Uani 1 1 d . . . . .
O1 O 0.4686(4) 0.7459(6) 0.64249(13) 0.0145(7) Uani 1 1 d . . . . .
C1 C 0.4734(6) 0.6203(8) 0.68883(19) 0.0135(10) Uani 1 1 d . . . . .
O2 O 0.1614(4) 0.5180(6) 0.62342(14) 0.0150(7) Uani 1 1 d . . . . .
H6 H 0.2123 0.6375 0.6206 0.022 Uiso 1 1 calc GR . . . .
C2 C 0.5645(6) 0.6931(9) 0.7332(2) 0.0176(11) Uani 1 1 d . . . . .
H1 H 0.6238 0.8276 0.7318 0.021 Uiso 1 1 calc R . . . .
O3 O 0.1105(5) -0.0265(6) 0.58801(14) 0.0210(8) Uani 1 1 d . . . . .
C3 C 0.5688(6) 0.5691(10) 0.7795(2) 0.0208(11) Uani 1 1 d . . . . .
H2 H 0.6314 0.6184 0.8099 0.025 Uiso 1 1 calc R . . . .
O4 O 0.3221(5) -0.0521(6) 0.52203(15) 0.0231(9) Uani 1 1 d . . . . .
C4 C 0.4815(7) 0.3724(10) 0.7813(2) 0.0209(12) Uani 1 1 d . . . . .
H3 H 0.4853 0.2861 0.8128 0.025 Uiso 1 1 calc R . . . .
C5 C 0.3888(6) 0.3035(9) 0.73694(19) 0.0166(10) Uani 1 1 d . . . . .
H4 H 0.3285 0.1698 0.7385 0.020 Uiso 1 1 calc R . . . .
C6 C 0.3821(6) 0.4270(8) 0.68983(18) 0.0116(9) Uani 1 1 d . . . . .
C7 C 0.2708(6) 0.3518(8) 0.64340(18) 0.0128(10) Uani 1 1 d . . . . .
H5 H 0.2003 0.2334 0.6578 0.015 Uiso 1 1 calc R . . . .
C8 C 0.3643(6) 0.2419(8) 0.59870(18) 0.0113(9) Uani 1 1 d . . . . .
H7 H 0.4411 0.1331 0.6163 0.014 Uiso 1 1 calc R . . . .
C9 C 0.4688(6) 0.3914(8) 0.56399(19) 0.0129(10) Uani 1 1 d . . . . .
H11 H 0.4997 0.3069 0.5324 0.015 Uiso 1 1 calc R . . . .
H12 H 0.4016 0.5185 0.5514 0.015 Uiso 1 1 calc R . . . .
C10 C 0.6237(6) 0.4780(8) 0.59285(18) 0.0132(10) Uani 1 1 d . . . . .
C11 C 0.6120(6) 0.7137(8) 0.6122(2) 0.0159(10) Uani 1 1 d . . . . .
H15 H 0.7109 0.7502 0.6346 0.019 Uiso 1 1 calc R . . . .
H16 H 0.6075 0.8150 0.5814 0.019 Uiso 1 1 calc R . . . .
C12 C 0.1187(6) 0.2776(9) 0.5153(2) 0.0192(11) Uani 1 1 d . . . . .
H8 H 0.0436 0.1995 0.4903 0.029 Uiso 1 1 calc GR . . . .
H9 H 0.1963 0.3643 0.4955 0.029 Uiso 1 1 calc GR . . . .
H10 H 0.0563 0.3763 0.5375 0.029 Uiso 1 1 calc GR . . . .
C13 C 0.7587(7) 0.3643(9) 0.5984(2) 0.0191(11) Uani 1 1 d . . . . .
H13 H 0.769(8) 0.230(13) 0.581(3) 0.037(19) Uiso 1 1 d . . . . .
H14 H 0.852(7) 0.435(10) 0.615(2) 0.015(14) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 116.8(2) . . ?
O3 S1 C8 108.4(2) . . ?
O3 S1 C12 108.4(2) . . ?
O4 S1 C8 108.2(2) . . ?
O4 S1 C12 108.1(2) . . ?
C12 S1 C8 106.4(2) . . ?
C1 O1 C11 112.3(4) . . ?
C2 C1 O1 119.7(4) . . ?
C2 C1 C6 121.5(5) . . ?
C6 C1 O1 118.8(4) . . ?
C1 C2 C3 119.9(5) . . ?
C2 C3 C4 120.0(5) . . ?
C5 C4 C3 119.6(5) . . ?
C4 C5 C6 121.3(5) . . ?
C1 C6 C5 117.8(4) . . ?
C1 C6 C7 122.8(4) . . ?
C5 C6 C7 119.4(4) . . ?
O2 C7 C6 113.9(4) . . ?
O2 C7 C8 111.8(4) . . ?
C6 C7 C8 113.1(4) . . ?
C7 C8 S1 110.4(3) . . ?
C7 C8 C9 117.9(4) . . ?
C9 C8 S1 108.5(3) . . ?
C10 C9 C8 113.7(4) . . ?
C11 C10 C9 114.5(4) . . ?
C13 C10 C9 123.4(5) . . ?
C13 C10 C11 122.0(5) . . ?
O1 C11 C10 111.3(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.446(4) . ?
S1 O4 1.449(4) . ?
S1 C8 1.801(5) . ?
S1 C12 1.756(5) . ?
O1 C1 1.394(6) . ?
O1 C11 1.446(6) . ?
C1 C2 1.386(7) . ?
C1 C6 1.390(7) . ?
O2 C7 1.424(6) . ?
C2 C3 1.388(8) . ?
C3 C4 1.392(8) . ?
C4 C5 1.386(7) . ?
C5 C6 1.404(7) . ?
C6 C7 1.519(6) . ?
C7 C8 1.545(6) . ?
C8 C9 1.547(6) . ?
C9 C10 1.525(7) . ?
C10 C11 1.514(7) . ?
C10 C13 1.304(8) . ?
