#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:57:49 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286145 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/68/7246854.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_7246854
loop_
_publ_author_name
'Liao, Tian-Ming'
'Ma, Wen-Jiang'
'Gao, Yu-Ning'
'Bian, Ming'
'Jiang, Min'
'Liu, Jin-Tao'
'Chen, Hui-Yu'
'Liu, Zhen-Jiang'
_publ_section_title
;
 Facile synthesis of (polyfluoro)alkanesulfinyl 4-isoxazolines: a stepwise
 solvent- and catalyst-free approach or a one-pot process in water
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              5233
_journal_page_last               5239
_journal_paper_doi               10.1039/D3GC00557G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C16 H11 F3 O2 S'
_chemical_formula_weight         324.31
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-05-04 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.4230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8998(2)
_cell_length_b                   16.2836(4)
_cell_length_c                   10.5436(3)
_cell_measurement_reflns_used    6827
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.948
_cell_measurement_theta_min      4.760
_cell_volume                     1457.88(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13887
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.705
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0192P)²+0.7644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0746
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2394
_reflns_number_total             2840
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc00557g2.cif
_cod_data_source_block           mo_d8v23144_0m
_cod_depositor_comments
'Adding full bibliography for 7246851--7246854.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246854
_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. 
;
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.970
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.20219(5) 0.43960(3) 0.60032(4) 0.03339(12) Uani 1 1 d . . . . .
F1 F 0.37644(12) 0.43596(8) 0.43394(10) 0.0526(3) Uani 1 1 d . . . . .
F2 F 0.27609(17) 0.32036(7) 0.46052(12) 0.0665(4) Uani 1 1 d . . . . .
F3 F 0.13052(13) 0.41521(9) 0.34558(11) 0.0612(4) Uani 1 1 d . . . . .
O1 O 0.34719(15) 0.28880(8) 0.75721(14) 0.0497(4) Uani 1 1 d . . . . .
O2 O 0.17952(14) 0.52844(8) 0.57390(13) 0.0447(3) Uani 1 1 d . . . . .
C1 C 0.68601(19) 0.35573(10) 0.66907(16) 0.0324(4) Uani 1 1 d . . . . .
H1 H 0.6423 0.4038 0.6234 0.039 Uiso 1 1 calc R U . . .
C2 C 0.8323(2) 0.32917(11) 0.66625(17) 0.0374(4) Uani 1 1 d . . . . .
H2 H 0.8866 0.3584 0.6167 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8989(2) 0.25995(12) 0.73588(19) 0.0447(5) Uani 1 1 d . . . . .
H3 H 0.9996 0.2427 0.7355 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8176(2) 0.21587(12) 0.8062(2) 0.0475(5) Uani 1 1 d . . . . .
H4 H 0.8631 0.1687 0.8537 0.057 Uiso 1 1 calc R U . . .
C5 C 0.6697(2) 0.24098(11) 0.80699(18) 0.0399(4) Uani 1 1 d . . . . .
H5 H 0.6138 0.2102 0.8534 0.048 Uiso 1 1 calc R U . . .
C6 C 0.60317(19) 0.31174(10) 0.73918(16) 0.0301(4) Uani 1 1 d . . . . .
C7 C 0.44363(19) 0.33753(10) 0.74102(16) 0.0323(4) Uani 1 1 d . . . . .
C8 C 0.39773(18) 0.42576(10) 0.71507(16) 0.0291(4) Uani 1 1 d . . . . .
C9 C 0.46637(19) 0.49455(10) 0.77300(16) 0.0307(4) Uani 1 1 d . . . . .
H9 H 0.4130 0.5431 0.7377 0.037 Uiso 1 1 calc R U . . .
C10 C 0.61145(19) 0.50689(10) 0.88272(16) 0.0311(4) Uani 1 1 d . . . . .
C11 C 0.6781(2) 0.58516(11) 0.89989(19) 0.0414(4) Uani 1 1 d . . . . .
H11 H 0.6300 0.6277 0.8415 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8144(2) 0.60086(13) 1.0021(2) 0.0485(5) Uani 1 1 d . . . . .
H12 H 0.8585 0.6538 1.0126 0.058 Uiso 1 1 calc R U . . .
C13 C 0.8855(2) 0.53924(14) 1.08828(19) 0.0483(5) Uani 1 1 d . . . . .
H13 H 0.9793 0.5497 1.1564 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8189(2) 0.46217(13) 1.07461(18) 0.0437(5) Uani 1 1 d . . . . .
H14 H 0.8667 0.4204 1.1347 0.052 Uiso 1 1 calc R U . . .
C15 C 0.6828(2) 0.44576(11) 0.97354(16) 0.0361(4) Uani 1 1 d . . . . .
H15 H 0.6378 0.3931 0.9658 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2509(2) 0.39989(11) 0.45183(17) 0.0380(4) Uani 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'
F F 0.0171 0.0103 '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
O2 S1 C8 107.32(7) . . ?
O2 S1 C16 103.59(8) . . ?
C8 S1 C16 95.70(7) . . ?
C2 C1 C6 120.27(16) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.17(17) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.97(17) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.18(17) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.14(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.24(16) . . ?
C1 C6 C7 121.50(14) . . ?
C5 C6 C7 119.24(15) . . ?
O1 C7 C6 122.26(16) . . ?
O1 C7 C8 119.07(15) . . ?
C6 C7 C8 118.59(14) . . ?
C9 C8 C7 131.33(15) . . ?
C9 C8 S1 114.72(12) . . ?
C7 C8 S1 113.37(11) . . ?
C8 C9 C10 130.61(16) . . ?
C8 C9 H9 114.7 . . ?
C10 C9 H9 114.7 . . ?
C11 C10 C15 118.32(16) . . ?
C11 C10 C9 117.87(16) . . ?
C15 C10 C9 123.76(15) . . ?
C12 C11 C10 120.63(18) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.17(19) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.87(18) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.56(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.40(17) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
F2 C16 F3 108.87(15) . . ?
F2 C16 F1 108.30(16) . . ?
F3 C16 F1 107.45(15) . . ?
F2 C16 S1 111.21(13) . . ?
F3 C16 S1 108.26(12) . . ?
F1 C16 S1 112.62(12) . . ?
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 O2 1.4757(13) . ?
S1 C8 1.8116(16) . ?
S1 C16 1.8613(18) . ?
F1 C16 1.325(2) . ?
F2 C16 1.313(2) . ?
F3 C16 1.322(2) . ?
O1 C7 1.218(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.389(2) . ?
C1 H1 0.9400 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.486(2) . ?
C7 C8 1.496(2) . ?
C8 C9 1.333(2) . ?
C9 C10 1.467(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.395(2) . ?
C10 C15 1.395(2) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.379(2) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O2 0.94 2.28 2.832(2) 116.7 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.7(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C1 C6 C7 -178.31(15) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 179.84(16) . . . . ?
C1 C6 C7 O1 152.63(17) . . . . ?
C5 C6 C7 O1 -26.0(2) . . . . ?
C1 C6 C7 C8 -24.2(2) . . . . ?
C5 C6 C7 C8 157.19(15) . . . . ?
O1 C7 C8 C9 128.4(2) . . . . ?
C6 C7 C8 C9 -54.7(2) . . . . ?
O1 C7 C8 S1 -42.2(2) . . . . ?
C6 C7 C8 S1 134.70(13) . . . . ?
O2 S1 C8 C9 13.36(15) . . . . ?
C16 S1 C8 C9 119.53(13) . . . . ?
O2 S1 C8 C7 -174.39(11) . . . . ?
C16 S1 C8 C7 -68.23(13) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
S1 C8 C9 C10 170.52(14) . . . . ?
C8 C9 C10 C11 163.00(17) . . . . ?
C8 C9 C10 C15 -19.5(3) . . . . ?
C15 C10 C11 C12 2.0(3) . . . . ?
C9 C10 C11 C12 179.58(16) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C11 C10 C15 C14 -2.3(2) . . . . ?
C9 C10 C15 C14 -179.69(16) . . . . ?
O2 S1 C16 F2 179.54(12) . . . . ?
C8 S1 C16 F2 70.15(13) . . . . ?
O2 S1 C16 F3 -60.89(13) . . . . ?
C8 S1 C16 F3 -170.28(12) . . . . ?
O2 S1 C16 F1 57.77(14) . . . . ?
C8 S1 C16 F1 -51.62(14) . . . . ?
