#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/95/7119535.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_7119535
loop_
_publ_author_name
'Wang, Li-Jing'
'Chen, Manman'
'Qi, Lin'
'Xu, Zhidong'
'Li, Wei'
_publ_section_title
;
 Copper-mediated oxysulfonylation of alkenyl oximes with sodium
 sulfinates: a facile synthesis of isoxazolines featuring a sulfone
 substituent.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2056
_journal_page_last               2059
_journal_paper_doi               10.1039/c7cc00090a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-12-26 deposited with the CCDC.
2017-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.9760(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.0767(10)
_cell_length_b                   10.7938(6)
_cell_length_c                   8.1475(5)
_cell_measurement_reflns_used    3266
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.63
_cell_measurement_theta_min      2.20
_cell_volume                     1588.76(16)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11473
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.9056
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0515P)²+0.3063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                2653
_reflns_number_total             3958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc00090a2.cif
_cod_data_source_block           chenman
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7119535.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7119535
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.06169(8) 0.22026(14) 0.02278(18) 0.0592(4) Uani 1 1 d .
O1 O 0.26381(8) -0.03713(13) 0.34109(17) 0.0770(4) Uani 1 1 d .
O2 O 0.35178(8) 0.13694(16) 0.36745(19) 0.0876(5) Uani 1 1 d .
O3 O 0.13714(7) 0.21096(13) -0.01388(15) 0.0686(4) Uani 1 1 d .
S1 S 0.30001(3) 0.06647(5) 0.26847(6) 0.06119(16) Uani 1 1 d .
C1 C -0.08417(9) 0.21203(15) 0.1392(2) 0.0543(4) Uani 1 1 d .
H1 H -0.0721 0.2785 0.0725 0.065 Uiso 1 1 calc R
C2 C -0.15499(10) 0.20093(18) 0.1944(2) 0.0641(5) Uani 1 1 d .
H2 H -0.1904 0.2601 0.1651 0.077 Uiso 1 1 calc R
C3 C -0.17390(11) 0.10251(19) 0.2931(2) 0.0647(5) Uani 1 1 d .
H3 H -0.2217 0.0959 0.3309 0.078 Uiso 1 1 calc R
C4 C -0.12176(11) 0.01469(18) 0.3351(2) 0.0625(5) Uani 1 1 d .
H4 H -0.1345 -0.0522 0.4003 0.075 Uiso 1 1 calc R
C5 C -0.05033(10) 0.02505(16) 0.2809(2) 0.0544(4) Uani 1 1 d .
H5 H -0.0153 -0.0347 0.3105 0.065 Uiso 1 1 calc R
C6 C -0.03038(9) 0.12425(14) 0.18238(18) 0.0452(3) Uani 1 1 d .
C7 C 0.04516(9) 0.13517(14) 0.12398(18) 0.0463(4) Uani 1 1 d .
C8 C 0.10860(9) 0.05266(16) 0.1730(2) 0.0551(4) Uani 1 1 d .
H8A H 0.0999 -0.0320 0.1375 0.066 Uiso 1 1 calc R
H8B H 0.1182 0.0539 0.2909 0.066 Uiso 1 1 calc R
C9 C 0.17139(9) 0.11144(16) 0.0823(2) 0.0549(4) Uani 1 1 d .
H9 H 0.1930 0.0505 0.0087 0.066 Uiso 1 1 calc R
C10 C 0.23226(10) 0.17117(16) 0.1886(2) 0.0589(4) Uani 1 1 d .
H10A H 0.2098 0.2131 0.2796 0.071 Uiso 1 1 calc R
H10B H 0.2567 0.2335 0.1240 0.071 Uiso 1 1 calc R
C11 C 0.34416(9) 0.01445(17) 0.0926(2) 0.0564(4) Uani 1 1 d .
C12 C 0.39142(11) 0.0923(2) 0.0128(3) 0.0773(6) Uani 1 1 d .
H12 H 0.4016 0.1711 0.0540 0.093 Uiso 1 1 calc R
C13 C 0.42356(13) 0.0520(2) -0.1291(3) 0.0892(7) Uani 1 1 d .
H13 H 0.4549 0.1050 -0.1837 0.107 Uiso 1 1 calc R
C14 C 0.41031(11) -0.0648(2) -0.1918(3) 0.0768(6) Uani 1 1 d .
C15 C 0.36341(12) -0.1407(2) -0.1100(3) 0.0761(6) Uani 1 1 d .
H15 H 0.3541 -0.2201 -0.1501 0.091 Uiso 1 1 calc R
C16 C 0.32959(11) -0.10216(18) 0.0309(3) 0.0683(5) Uani 1 1 d .
H16 H 0.2972 -0.1546 0.0836 0.082 Uiso 1 1 calc R
C17 C 0.44631(15) -0.1053(3) -0.3479(3) 0.1162(10) Uani 1 1 d .
H17A H 0.4168 -0.0779 -0.4412 0.174 Uiso 1 1 calc R
H17B H 0.4501 -0.1940 -0.3496 0.174 Uiso 1 1 calc R
H17C H 0.4949 -0.0697 -0.3519 0.174 Uiso 1 1 calc R
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'
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
C7 N1 O3 109.59(13)
N1 O3 C9 109.59(12)
O2 S1 O1 118.71(10)
O2 S1 C11 108.82(9)
O1 S1 C11 108.31(9)
O2 S1 C10 107.31(9)
O1 S1 C10 109.22(9)
C11 S1 C10 103.40(8)
C2 C1 C6 120.43(16)
C2 C1 H1 119.8
C6 C1 H1 119.8
C1 C2 C3 120.55(17)
C1 C2 H2 119.7
C3 C2 H2 119.7
C4 C3 C2 119.64(18)
C4 C3 H3 120.2
C2 C3 H3 120.2
C3 C4 C5 120.36(17)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.60(16)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 118.42(16)
C5 C6 C7 120.74(14)
C1 C6 C7 120.84(14)
N1 C7 C6 120.59(14)
N1 C7 C8 113.99(15)
C6 C7 C8 125.42(14)
C7 C8 C9 101.58(13)
C7 C8 H8A 111.5
C9 C8 H8A 111.5
C7 C8 H8B 111.5
C9 C8 H8B 111.5
H8A C8 H8B 109.3
O3 C9 C8 105.07(13)
O3 C9 C10 106.25(14)
C8 C9 C10 116.05(14)
O3 C9 H9 109.7
C8 C9 H9 109.7
C10 C9 H9 109.7
C9 C10 S1 114.58(12)
C9 C10 H10A 108.6
S1 C10 H10A 108.6
C9 C10 H10B 108.6
S1 C10 H10B 108.6
H10A C10 H10B 107.6
C12 C11 C16 119.93(19)
C12 C11 S1 119.79(15)
C16 C11 S1 120.24(14)
C11 C12 C13 119.2(2)
C11 C12 H12 120.4
C13 C12 H12 120.4
C14 C13 C12 121.7(2)
C14 C13 H13 119.1
C12 C13 H13 119.1
C15 C14 C13 118.0(2)
C15 C14 C17 121.8(2)
C13 C14 C17 120.1(2)
C14 C15 C16 121.5(2)
C14 C15 H15 119.3
C16 C15 H15 119.3
C11 C16 C15 119.59(19)
C11 C16 H16 120.2
C15 C16 H16 120.2
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 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
N1 C7 1.277(2)
N1 O3 1.4099(18)
O1 S1 1.4337(14)
O2 S1 1.4327(14)
O3 C9 1.455(2)
S1 C11 1.7560(19)
S1 C10 1.7737(18)
C1 C2 1.377(2)
C1 C6 1.394(2)
C1 H1 0.9300
C2 C3 1.382(3)
C2 H2 0.9300
C3 C4 1.372(3)
C3 H3 0.9300
C4 C5 1.384(3)
C4 H4 0.9300
C5 C6 1.393(2)
C5 H5 0.9300
C6 C7 1.466(2)
C7 C8 1.496(2)
C8 C9 1.515(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.520(2)
C9 H9 0.9800
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.377(3)
C11 C16 1.377(3)
C12 C13 1.382(3)
C12 H12 0.9300
C13 C14 1.378(3)
C13 H13 0.9300
C14 C15 1.369(3)
C14 C17 1.513(3)
C15 C16 1.383(3)
C15 H15 0.9300
C16 H16 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139187390
