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#$Date: 2023-09-05 22:57:49 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286145 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/68/7246851.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_7246851
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            'C17 H14 F3 N O2 S'
_chemical_formula_weight         353.35
_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
;
2023-01-17 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.207(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3303(17)
_cell_length_b                   17.815(3)
_cell_length_c                   10.8360(18)
_cell_measurement_reflns_used    7762
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.712
_cell_measurement_theta_min      4.660
_cell_volume                     1667.6(5)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0577
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15324
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.058
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0578
_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)+(0.0738P)²+0.9695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1624
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2432
_reflns_number_total             3088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc00557g2.cif
_cod_data_source_block           mo_d8v21849_0m
_cod_depositor_comments
'Adding full bibliography for 7246851--7246854.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246851
_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   0.955
_shelx_estimated_absorpt_t_max   0.972
_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 0.67854(8) 0.50317(4) 0.27445(7) 0.0420(3) Uani 1 1 d . . . . .
F1 F 0.3944(2) 0.55965(12) 0.1750(2) 0.0807(7) Uani 1 1 d . . . . .
F2 F 0.4862(3) 0.54441(14) 0.3866(3) 0.0906(8) Uani 1 1 d . . . . .
F3 F 0.5688(3) 0.63329(11) 0.2985(3) 0.0907(8) Uani 1 1 d . . . . .
O1 O 0.6011(2) 0.29049(11) 0.2792(2) 0.0483(5) Uani 1 1 d . . . . .
O2 O 0.6838(3) 0.52251(13) 0.1437(2) 0.0585(6) Uani 1 1 d . . . . .
N1 N 0.4836(3) 0.30664(14) 0.1447(2) 0.0478(6) Uani 1 1 d . . . . .
C1 C 0.4461(3) 0.38727(16) 0.1513(3) 0.0411(6) Uani 1 1 d . . . . .
H1 H 0.4326 0.4123 0.0671 0.049 Uiso 1 1 calc R U . . .
C2 C 0.5895(3) 0.41608(15) 0.2615(3) 0.0377(6) Uani 1 1 d . . . . .
C3 C 0.6669(3) 0.35705(15) 0.3331(3) 0.0405(6) Uani 1 1 d . . . . .
C4 C 0.8036(3) 0.35035(16) 0.4567(3) 0.0421(6) Uani 1 1 d . . . . .
C5 C 0.8313(4) 0.40244(18) 0.5585(3) 0.0524(8) Uani 1 1 d . . . . .
H5 H 0.7635 0.4424 0.5477 0.063 Uiso 1 1 calc R U . . .
C6 C 0.9585(4) 0.3952(2) 0.6753(4) 0.0697(10) Uani 1 1 d . . . . .
H6 H 0.9762 0.4305 0.7429 0.084 Uiso 1 1 calc R U . . .
C7 C 1.0594(4) 0.3367(2) 0.6930(4) 0.0727(11) Uani 1 1 d . . . . .
H7 H 1.1446 0.3319 0.7726 0.087 Uiso 1 1 calc R U . . .
C8 C 1.0347(4) 0.2852(2) 0.5937(4) 0.0675(10) Uani 1 1 d . . . . .
H8 H 1.1045 0.2460 0.6051 0.081 Uiso 1 1 calc R U . . .
C9 C 0.9067(4) 0.29092(18) 0.4764(4) 0.0566(8) Uani 1 1 d . . . . .
H9 H 0.8893 0.2549 0.4102 0.068 Uiso 1 1 calc R U . . .
C10 C 0.2989(3) 0.39370(16) 0.1797(3) 0.0408(6) Uani 1 1 d . . . . .
C11 C 0.1623(3) 0.41363(18) 0.0811(3) 0.0540(8) Uani 1 1 d . . . . .
H11 H 0.1606 0.4255 -0.0030 0.065 Uiso 1 1 calc R U . . .
C12 C 0.0252(4) 0.4166(2) 0.1042(5) 0.0716(11) Uani 1 1 d . . . . .
H12 H -0.0672 0.4300 0.0362 0.086 Uiso 1 1 calc R U . . .
C13 C 0.0284(4) 0.3995(2) 0.2280(5) 0.0693(10) Uani 1 1 d . . . . .
H13 H -0.0627 0.4010 0.2440 0.083 Uiso 1 1 calc R U . . .
C14 C 0.1633(4) 0.3803(2) 0.3280(4) 0.0699(10) Uani 1 1 d . . . . .
H14 H 0.1641 0.3694 0.4122 0.084 Uiso 1 1 calc R U . . .
C15 C 0.2992(4) 0.3769(2) 0.3054(3) 0.0578(8) Uani 1 1 d . . . . .
H15 H 0.3911 0.3634 0.3741 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5210(4) 0.56307(18) 0.2825(4) 0.0568(8) Uani 1 1 d . . . . .
C17 C 0.5660(5) 0.2938(2) 0.0544(4) 0.0722(11) Uani 1 1 d . . . . .
H17A H 0.6501 0.3288 0.0748 0.108 Uiso 1 1 calc R U . . .
H17B H 0.4958 0.3008 -0.0361 0.108 Uiso 1 1 calc R U . . .
H17C H 0.6058 0.2435 0.0658 0.108 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 108.60(13) . . ?
O2 S1 C16 103.09(15) . . ?
C2 S1 C16 98.90(14) . . ?
C3 O1 N1 107.4(2) . . ?
C17 N1 O1 104.2(2) . . ?
C17 N1 C1 111.9(3) . . ?
O1 N1 C1 103.89(19) . . ?
N1 C1 C2 102.3(2) . . ?
N1 C1 C10 109.2(2) . . ?
C2 C1 C10 114.4(2) . . ?
N1 C1 H1 110.2 . . ?
C2 C1 H1 110.2 . . ?
C10 C1 H1 110.2 . . ?
C3 C2 C1 108.3(2) . . ?
C3 C2 S1 121.0(2) . . ?
C1 C2 S1 128.4(2) . . ?
C2 C3 O1 112.2(2) . . ?
C2 C3 C4 133.2(3) . . ?
O1 C3 C4 114.6(2) . . ?
C5 C4 C9 118.4(3) . . ?
C5 C4 C3 120.6(3) . . ?
C9 C4 C3 121.0(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 120.3(3) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C11 C10 C15 118.5(3) . . ?
C11 C10 C1 120.6(3) . . ?
C15 C10 C1 120.9(3) . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
F1 C16 F3 107.9(3) . . ?
F1 C16 F2 108.4(3) . . ?
F3 C16 F2 107.8(3) . . ?
F1 C16 S1 113.4(2) . . ?
F3 C16 S1 108.6(2) . . ?
F2 C16 S1 110.5(2) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 1.477(2) . ?
S1 C2 1.740(3) . ?
S1 C16 1.845(3) . ?
F1 C16 1.310(4) . ?
F2 C16 1.328(4) . ?
F3 C16 1.317(4) . ?
O1 C3 1.361(3) . ?
O1 N1 1.484(3) . ?
N1 C17 1.473(4) . ?
N1 C1 1.486(4) . ?
C1 C2 1.507(4) . ?
C1 C10 1.521(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.344(4) . ?
C3 C4 1.464(4) . ?
C4 C5 1.389(4) . ?
C4 C9 1.392(4) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.365(4) . ?
C10 C15 1.393(4) . ?
C11 C12 1.394(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
C1 H1 O2 0.98 2.42 3.367(3) 161.8 3_665
C1 H1 O2 0.98 2.42 3.367(3) 161.8 3_665
C1 H1 O2 0.98 2.42 3.367(3) 161.8 3_665
C1 H1 O2 0.98 2.42 3.367(3) 161.8 3_665
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
C3 O1 N1 C17 95.1(3) . . . . ?
C3 O1 N1 C1 -22.2(3) . . . . ?
C17 N1 C1 C2 -88.1(3) . . . . ?
O1 N1 C1 C2 23.7(2) . . . . ?
C17 N1 C1 C10 150.4(3) . . . . ?
O1 N1 C1 C10 -97.8(2) . . . . ?
N1 C1 C2 C3 -18.4(3) . . . . ?
C10 C1 C2 C3 99.5(3) . . . . ?
N1 C1 C2 S1 144.0(2) . . . . ?
C10 C1 C2 S1 -98.1(3) . . . . ?
O2 S1 C2 C3 116.8(2) . . . . ?
C16 S1 C2 C3 -136.1(2) . . . . ?
O2 S1 C2 C1 -43.6(3) . . . . ?
C16 S1 C2 C1 63.5(3) . . . . ?
C1 C2 C3 O1 5.0(3) . . . . ?
S1 C2 C3 O1 -158.98(19) . . . . ?
C1 C2 C3 C4 -173.5(3) . . . . ?
S1 C2 C3 C4 22.5(4) . . . . ?
N1 O1 C3 C2 11.0(3) . . . . ?
N1 O1 C3 C4 -170.2(2) . . . . ?
C2 C3 C4 C5 35.0(4) . . . . ?
O1 C3 C4 C5 -143.5(3) . . . . ?
C2 C3 C4 C9 -146.5(3) . . . . ?
O1 C3 C4 C9 35.1(4) . . . . ?
C9 C4 C5 C6 0.4(5) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C6 C7 C8 C9 -1.4(6) . . . . ?
C7 C8 C9 C4 1.7(5) . . . . ?
C5 C4 C9 C8 -1.2(5) . . . . ?
C3 C4 C9 C8 -179.7(3) . . . . ?
N1 C1 C10 C11 -105.2(3) . . . . ?
C2 C1 C10 C11 140.9(3) . . . . ?
N1 C1 C10 C15 72.5(3) . . . . ?
C2 C1 C10 C15 -41.4(4) . . . . ?
C15 C10 C11 C12 -0.6(5) . . . . ?
C1 C10 C11 C12 177.2(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 C14 0.4(6) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C13 C14 C15 C10 0.4(6) . . . . ?
C11 C10 C15 C14 0.3(5) . . . . ?
C1 C10 C15 C14 -177.5(3) . . . . ?
O2 S1 C16 F1 49.0(3) . . . . ?
C2 S1 C16 F1 -62.6(3) . . . . ?
O2 S1 C16 F3 -71.0(3) . . . . ?
C2 S1 C16 F3 177.4(2) . . . . ?
O2 S1 C16 F2 171.0(2) . . . . ?
C2 S1 C16 F2 59.4(3) . . . . ?
