# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_14464_auto
_database_code_depnum_ccdc_archive 'CCDC 2363463'
loop_
_audit_author_name
_audit_author_address
oxime
;Fuyang Normal University
China
;
_audit_update_record             
;
2024-06-18 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2024-06-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N2 O3 S'
_chemical_formula_sum            'C14 H14 N2 O3 S'
_chemical_formula_weight         290.33
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   15.053(3)
_cell_length_b                   5.5099(9)
_cell_length_c                   16.412(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.360(14)
_cell_angle_gamma                90
_cell_volume                     1361.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    576
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.3240
_cell_measurement_theta_min      3.6550
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.1125
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5321
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.482
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  85.00   1.00    7.50    --   16.96  57.00  60.00   83
  2  ω    -51.00  33.00   1.00    7.50    --   16.96 -57.00 -60.00   84
  3  ω    -33.00  -4.00   1.00    7.50    --  -17.43 -77.00  60.00   29
  4  ω    -45.00 -20.00   1.00    7.50    --  -17.43  77.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0130769000
_diffrn_orient_matrix_UB_12      -0.1231171000
_diffrn_orient_matrix_UB_13      -0.0039370000
_diffrn_orient_matrix_UB_21      0.0377051000
_diffrn_orient_matrix_UB_22      -0.0363989000
_diffrn_orient_matrix_UB_23      0.0231204000
_diffrn_orient_matrix_UB_31      -0.0250203000
_diffrn_orient_matrix_UB_32      0.0098415000
_diffrn_orient_matrix_UB_33      0.0363127000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1479
_reflns_number_total             2675
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0713
_refine_ls_restrained_S_all      1.829
_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)+(0.0297P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1329
_refine_special_details          ?
_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
2. Restrained distances
 N1-N1
 1.5 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1 C 0.3280(2) 0.4313(6) 0.4143(2) 0.0371(10) Uani 1 1 d . . . . .
H1A H 0.3573 0.3876 0.3639 0.045 Uiso 1 1 calc R U . . .
H1B H 0.3216 0.6065 0.4155 0.045 Uiso 1 1 calc R U . . .
C2 C 0.3840(2) 0.3507(7) 0.4855(2) 0.0331(9) Uani 1 1 d . . . . .
C3 C 0.3790(2) 0.4700(7) 0.5664(2) 0.0332(9) Uani 1 1 d . . . . .
C4 C 0.3304(3) 0.6792(7) 0.5799(2) 0.0434(11) Uani 1 1 d . . . . .
H4 H 0.2991 0.7528 0.5376 0.052 Uiso 1 1 calc R U . . .
C5 C 0.3295(3) 0.7764(8) 0.6574(3) 0.0539(12) Uani 1 1 d . . . . .
H5 H 0.2977 0.9175 0.6680 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3756(3) 0.6636(8) 0.7184(2) 0.0546(12) Uani 1 1 d . . . . .
H6 H 0.3754 0.7257 0.7710 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4222(3) 0.4575(8) 0.7006(2) 0.0545(12) Uani 1 1 d . . . . .
H7 H 0.4533 0.3821 0.7427 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1726(2) 0.3766(7) 0.3226(2) 0.0324(9) Uani 1 1 d . . . . .
C9 C 0.1253(3) 0.5874(7) 0.3161(2) 0.0403(10) Uani 1 1 d . . . . .
H9 H 0.1180 0.6872 0.3612 0.048 Uiso 1 1 calc R U . . .
C10 C 0.0881(3) 0.6516(7) 0.2413(2) 0.0454(11) Uani 1 1 d . . . . .
H10 H 0.0560 0.7951 0.2367 0.054 Uiso 1 1 calc R U . . .
C11 C 0.0984(3) 0.5044(8) 0.1736(2) 0.0412(10) Uani 1 1 d . . . . .
C12 C 0.1457(3) 0.2928(7) 0.1820(2) 0.0445(11) Uani 1 1 d . . . . .
H12 H 0.1526 0.1917 0.1371 0.053 Uiso 1 1 calc R U . . .
C13 C 0.1834(2) 0.2272(7) 0.2559(2) 0.0416(10) Uani 1 1 d . . . . .
H13 H 0.2156 0.0838 0.2605 0.050 Uiso 1 1 calc R U . . .
C14 C 0.0574(3) 0.5776(8) 0.0928(2) 0.0675(14) Uani 1 1 d . . . . .
H14A H -0.0035 0.6227 0.1008 0.101 Uiso 1 1 calc R U . . .
H14B H 0.0603 0.4436 0.0555 0.101 Uiso 1 1 calc R U . . .
H14C H 0.0895 0.7130 0.0708 0.101 Uiso 1 1 calc R U . . .
N1 N 0.4402(2) 0.1769(6) 0.48136(18) 0.0424(9) Uani 1 1 d D . . A -1
N2 N 0.4258(2) 0.3577(6) 0.62644(18) 0.0445(9) Uani 1 1 d . . . . .
O1 O 0.17061(18) 0.4059(5) 0.48151(15) 0.0586(9) Uani 1 1 d . . . . .
O2 O 0.2327(2) 0.0364(5) 0.41798(16) 0.0609(9) Uani 1 1 d . . . . .
O3 O 0.4457(2) 0.0640(6) 0.40604(16) 0.0528(9) Uani 1 1 d . . . . .
S1 S 0.22068(7) 0.2934(2) 0.41719(6) 0.0431(3) Uani 1 1 d . . . . .
H3 H 0.487(3) -0.053(8) 0.417(3) 0.087(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.503(5) . ?
C1 S1 1.786(4) . ?
C2 C3 1.484(5) . ?
C2 N1 1.280(4) . ?
C3 C4 1.384(5) . ?
C3 N2 1.357(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.364(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.367(5) . ?
C7 H7 0.9300 . ?
C7 N2 1.336(4) . ?
C8 C9 1.366(4) . ?
C8 C13 1.381(5) . ?
C8 S1 1.769(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(5) . ?
C11 C12 1.372(5) . ?
C11 C14 1.514(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 O3 1.387(4) . ?
O1 S1 1.441(3) . ?
O2 S1 1.428(3) . ?
O3 H3 0.92(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
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 S1 110.9(2) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
C3 C2 C1 122.2(3) . . ?
N1 C2 C1 123.2(3) . . ?
N1 C2 C3 114.5(3) . . ?
C4 C3 C2 122.8(3) . . ?
N2 C3 C2 114.8(3) . . ?
N2 C3 C4 122.4(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.8(4) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 H7 118.0 . . ?
N2 C7 C6 124.1(4) . . ?
N2 C7 H7 118.0 . . ?
C9 C8 C13 120.6(3) . . ?
C9 C8 S1 119.9(3) . . ?
C13 C8 S1 119.5(3) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.5(4) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C14 120.0(4) . . ?
C12 C11 C10 118.5(4) . . ?
C12 C11 C14 121.5(4) . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.3(4) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 C12 119.3(4) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 N1 O3 115.2(3) . . ?
C7 N2 C3 116.7(3) . . ?
N1 O3 H3 101(3) . . ?
C8 S1 C1 103.38(16) . . ?
O1 S1 C1 108.30(17) . . ?
O1 S1 C8 108.58(18) . . ?
O2 S1 C1 107.92(19) . . ?
O2 S1 C8 108.42(18) . . ?
O2 S1 O1 119.12(18) . . ?

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 C2 C3 C4 -7.4(5) . . . . ?
C1 C2 C3 N2 172.5(3) . . . . ?
C1 C2 N1 O3 -0.6(5) . . . . ?
C2 C1 S1 C8 -172.0(3) . . . . ?
C2 C1 S1 O1 72.9(3) . . . . ?
C2 C1 S1 O2 -57.3(3) . . . . ?
C2 C3 C4 C5 179.7(3) . . . . ?
C2 C3 N2 C7 -179.2(3) . . . . ?
C3 C2 N1 O3 -179.8(3) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C3 N2 C7 0.7(5) . . . . ?
C4 C5 C6 C7 0.5(6) . . . . ?
C5 C6 C7 N2 0.1(6) . . . . ?
C6 C7 N2 C3 -0.7(6) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C9 C8 C13 C12 0.0(6) . . . . ?
C9 C8 S1 C1 -89.4(3) . . . . ?
C9 C8 S1 O1 25.4(3) . . . . ?
C9 C8 S1 O2 156.2(3) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C9 C10 C11 C14 -179.9(4) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
C11 C12 C13 C8 0.4(6) . . . . ?
C13 C8 C9 C10 -0.3(6) . . . . ?
C13 C8 S1 C1 90.5(3) . . . . ?
C13 C8 S1 O1 -154.6(3) . . . . ?
C13 C8 S1 O2 -23.8(4) . . . . ?
C14 C11 C12 C13 179.7(4) . . . . ?
N1 C2 C3 C4 171.9(3) . . . . ?
N1 C2 C3 N2 -8.2(5) . . . . ?
N2 C3 C4 C5 -0.2(6) . . . . ?
S1 C1 C2 C3 -84.5(4) . . . . ?
S1 C1 C2 N1 96.3(4) . . . . ?
S1 C8 C9 C10 179.7(3) . . . . ?
S1 C8 C13 C12 -180.0(3) . . . . ?


_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 1.052
_oxdiff_exptl_absorpt_empirical_full_min 0.936
