#------------------------------------------------------------------------------
#$Date: 2023-09-05 21:57:49 +0200 (Tue 05 de Sep de 2023) $
#$Revision: 286145 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/68/7246853.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_7246853
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            'C18 H16 F3 N O2 S'
_chemical_formula_weight         367.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-01-17 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                102.617(2)
_cell_angle_beta                 92.927(2)
_cell_angle_gamma                99.557(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9764(5)
_cell_length_b                   9.7004(6)
_cell_length_c                   10.5392(6)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      55.040
_cell_measurement_theta_min      4.376
_cell_volume                     879.46(9)
_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 0.984
_diffrn_measured_fraction_theta_max 0.985
_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  0.0665
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18169
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.183
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0569P)²+0.2614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3128
_reflns_number_total             3391
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc00557g2.cif
_cod_data_source_block           mo_d8v22527_0m
_cod_depositor_comments
'Adding full bibliography for 7246851--7246854.cif.'
_cod_database_code               7246853
_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   0.961
_shelx_estimated_absorpt_t_max   0.974
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.18775(4) 0.31515(4) 0.87182(3) 0.03161(14) Uani 1 1 d . . . . .
F1 F 0.35629(12) 0.16210(13) 0.97935(11) 0.0538(3) Uani 1 1 d . . . . .
F2 F 0.12583(13) 0.14435(12) 1.02680(11) 0.0539(3) Uani 1 1 d . . . . .
F3 F 0.17587(16) 0.03661(11) 0.83763(12) 0.0626(3) Uani 1 1 d . . . . .
O1 O 0.41225(12) 0.36692(12) 0.57728(10) 0.0355(3) Uani 1 1 d . . . . .
O2 O 0.25110(14) 0.43458(12) 0.98451(11) 0.0440(3) Uani 1 1 d . . . . .
N1 N 0.53700(14) 0.42311(14) 0.68413(12) 0.0345(3) Uani 1 1 d . . . . .
C1 C 0.28542(17) 0.32062(15) 0.63259(14) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.31839(16) 0.30841(15) 0.75564(14) 0.0305(3) Uani 1 1 d . . . . .
C3 C 0.48967(16) 0.34109(15) 0.78384(14) 0.0311(3) Uani 1 1 d . . . . .
H3 H 0.5181 0.4031 0.8725 0.037 Uiso 1 1 calc R U . . .
C4 C 0.56326(17) 0.20930(16) 0.76840(15) 0.0323(3) Uani 1 1 d . . . . .
C5 C 0.50157(19) 0.08111(18) 0.68150(16) 0.0399(4) Uani 1 1 d . . . . .
H5 H 0.4093 0.0736 0.6319 0.048 Uiso 1 1 calc R U . . .
C6 C 0.5737(2) -0.03650(18) 0.66651(17) 0.0459(4) Uani 1 1 d . . . . .
H6 H 0.5307 -0.1227 0.6066 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7081(2) -0.02700(19) 0.73933(19) 0.0479(4) Uani 1 1 d . . . . .
H7 H 0.7576 -0.1063 0.7292 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7698(2) 0.0998(2) 0.8274(2) 0.0497(4) Uani 1 1 d . . . . .
H8 H 0.8610 0.1061 0.8780 0.060 Uiso 1 1 calc R U . . .
C9 C 0.69847(19) 0.21795(18) 0.84202(18) 0.0419(4) Uani 1 1 d . . . . .
H9 H 0.7418 0.3040 0.9019 0.050 Uiso 1 1 calc R U . . .
C10 C 0.14401(18) 0.29245(16) 0.54841(14) 0.0333(3) Uani 1 1 d . . . . .
C11 C 0.0187(2) 0.19587(18) 0.56820(17) 0.0442(4) Uani 1 1 d . . . . .
H11 H 0.0256 0.1444 0.6336 0.053 Uiso 1 1 calc R U . . .
C12 C -0.1157(2) 0.1764(2) 0.4908(2) 0.0548(5) Uani 1 1 d . . . . .
H12 H -0.2021 0.1152 0.5064 0.066 Uiso 1 1 calc R U . . .
C13 C -0.1232(2) 0.2470(2) 0.39061(18) 0.0521(5) Uani 1 1 d . . . . .
H13 H -0.2147 0.2315 0.3378 0.062 Uiso 1 1 calc R U . . .
C14 C 0.0011(2) 0.34001(18) 0.36609(16) 0.0422(4) Uani 1 1 d . . . . .
C15 C 0.13404(19) 0.36416(17) 0.44747(15) 0.0366(3) Uani 1 1 d . . . . .
H15 H 0.2184 0.4296 0.4345 0.044 Uiso 1 1 calc R U . . .
C16 C -0.0053(3) 0.4150(3) 0.25536(19) 0.0591(5) Uani 1 1 d . . . . .
H16A H 0.0450 0.5144 0.2851 0.089 Uiso 1 1 calc R U . . .
H16B H -0.1104 0.4113 0.2259 0.089 Uiso 1 1 calc R U . . .
H16C H 0.0453 0.3675 0.1838 0.089 Uiso 1 1 calc R U . . .
C17 C 0.2156(2) 0.15427(18) 0.93145(16) 0.0396(4) Uani 1 1 d . . . . .
C18 C 0.5275(2) 0.57519(17) 0.72978(17) 0.0411(4) Uani 1 1 d . . . . .
H18A H 0.5334 0.6212 0.6568 0.062 Uiso 1 1 calc R U . . .
H18B H 0.6109 0.6219 0.7954 0.062 Uiso 1 1 calc R U . . .
H18C H 0.4320 0.5831 0.7674 0.062 Uiso 1 1 calc R U . . .
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'
N N 0.0061 0.0033 '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 C2 107.94(7) . . ?
O2 S1 C17 102.81(7) . . ?
C2 S1 C17 98.91(7) . . ?
C1 O1 N1 107.33(10) . . ?
C18 N1 C3 110.91(12) . . ?
C18 N1 O1 104.34(11) . . ?
C3 N1 O1 102.90(10) . . ?
C2 C1 O1 111.76(13) . . ?
C2 C1 C10 133.29(14) . . ?
O1 C1 C10 114.94(13) . . ?
C1 C2 C3 107.88(13) . . ?
C1 C2 S1 123.06(11) . . ?
C3 C2 S1 125.78(11) . . ?
N1 C3 C4 110.46(12) . . ?
N1 C3 C2 101.88(11) . . ?
C4 C3 C2 114.41(12) . . ?
N1 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
C5 C4 C9 118.74(15) . . ?
C5 C4 C3 122.22(14) . . ?
C9 C4 C3 119.03(14) . . ?
C4 C5 C6 121.01(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 119.96(16) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 119.52(16) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.68(17) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 120.08(16) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C15 119.69(15) . . ?
C11 C10 C1 120.78(14) . . ?
C15 C10 C1 119.53(15) . . ?
C12 C11 C10 119.46(17) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.06(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 121.63(16) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 118.19(16) . . ?
C13 C14 C16 121.91(17) . . ?
C15 C14 C16 119.90(18) . . ?
C14 C15 C10 120.88(16) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1 C17 F3 109.34(15) . . ?
F1 C17 F2 107.83(13) . . ?
F3 C17 F2 108.18(14) . . ?
F1 C17 S1 112.93(12) . . ?
F3 C17 S1 110.81(11) . . ?
F2 C17 S1 107.59(11) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 1.4790(11) . ?
S1 C2 1.7366(15) . ?
S1 C17 1.8534(17) . ?
F1 C17 1.320(2) . ?
F2 C17 1.329(2) . ?
F3 C17 1.320(2) . ?
O1 C1 1.3601(18) . ?
O1 N1 1.4898(16) . ?
N1 C18 1.467(2) . ?
N1 C3 1.4887(19) . ?
C1 C2 1.350(2) . ?
C1 C10 1.462(2) . ?
C2 C3 1.518(2) . ?
C3 C4 1.516(2) . ?
C3 H3 0.9900 . ?
C4 C5 1.383(2) . ?
C4 C9 1.387(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.387(2) . ?
C8 H8 0.9400 . ?
C9 H9 0.9400 . ?
C10 C11 1.395(2) . ?
C10 C15 1.399(2) . ?
C11 C12 1.384(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.389(2) . ?
C14 C16 1.507(3) . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
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
C3 H3 O2 0.99 2.57 3.3953(18) 140.8 2_667
C18 H18A O1 0.97 2.56 3.457(2) 153.5 2_666
C3 H3 O2 0.99 2.57 3.3953(18) 140.8 2_667
C18 H18A O1 0.97 2.56 3.457(2) 153.5 2_666
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
C1 O1 N1 C18 -89.25(13) . . . . ?
C1 O1 N1 C3 26.63(13) . . . . ?
N1 O1 C1 C2 -14.30(15) . . . . ?
N1 O1 C1 C10 166.58(11) . . . . ?
O1 C1 C2 C3 -4.17(16) . . . . ?
C10 C1 C2 C3 174.72(15) . . . . ?
O1 C1 C2 S1 156.38(10) . . . . ?
C10 C1 C2 S1 -24.7(2) . . . . ?
O2 S1 C2 C1 -121.71(13) . . . . ?
C17 S1 C2 C1 131.63(13) . . . . ?
O2 S1 C2 C3 35.30(14) . . . . ?
C17 S1 C2 C3 -71.36(13) . . . . ?
C18 N1 C3 C4 -154.29(13) . . . . ?
O1 N1 C3 C4 94.63(13) . . . . ?
C18 N1 C3 C2 83.76(14) . . . . ?
O1 N1 C3 C2 -27.31(13) . . . . ?
C1 C2 C3 N1 20.47(15) . . . . ?
S1 C2 C3 N1 -139.41(11) . . . . ?
C1 C2 C3 C4 -98.72(14) . . . . ?
S1 C2 C3 C4 101.40(14) . . . . ?
N1 C3 C4 C5 -84.85(17) . . . . ?
C2 C3 C4 C5 29.4(2) . . . . ?
N1 C3 C4 C9 93.94(17) . . . . ?
C2 C3 C4 C9 -151.83(14) . . . . ?
C9 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C6 178.02(16) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C5 C4 C9 C8 0.3(3) . . . . ?
C3 C4 C9 C8 -178.51(16) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C2 C1 C10 C11 -24.0(2) . . . . ?
O1 C1 C10 C11 154.84(14) . . . . ?
C2 C1 C10 C15 155.48(16) . . . . ?
O1 C1 C10 C15 -25.66(19) . . . . ?
C15 C10 C11 C12 -2.5(3) . . . . ?
C1 C10 C11 C12 177.01(16) . . . . ?
C10 C11 C12 C13 3.2(3) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C12 C13 C14 C16 178.75(18) . . . . ?
C13 C14 C15 C10 2.3(2) . . . . ?
C16 C14 C15 C10 -178.05(15) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C1 C10 C15 C14 -179.80(13) . . . . ?
O2 S1 C17 F1 -51.73(13) . . . . ?
C2 S1 C17 F1 59.09(13) . . . . ?
O2 S1 C17 F3 -174.79(12) . . . . ?
C2 S1 C17 F3 -63.97(13) . . . . ?
O2 S1 C17 F2 67.14(12) . . . . ?
C2 S1 C17 F2 177.96(11) . . . . ?
