# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_190113a
_database_code_depnum_ccdc_archive 'CCDC 1906721'
loop_
_audit_author_name
_audit_author_address
HPIBT
;Northwest Agricultural  and Forestry University
China
;
_audit_update_record             
;
2019-03-30 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 N2 O3 S'
_chemical_formula_weight         310.32

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   5.6795(5)
_cell_length_b                   28.701(3)
_cell_length_c                   7.8681(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.117(2)
_cell_angle_gamma                90.00
_cell_volume                     1282.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1452
_cell_measurement_theta_min      2.839
_cell_measurement_theta_max      26.43

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9240
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6289
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2242
_reflns_number_gt                1516
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0805P)²+0.8369P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2242
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2959(7) 0.90285(12) 0.3792(5) 0.0528(9) Uani 1 1 d . . .
N2 N 0.0372(6) 0.66809(11) 0.2627(4) 0.0437(8) Uani 1 1 d . . .
O1 O 0.5939(6) 0.86347(11) 0.5082(4) 0.0611(9) Uani 1 1 d . . .
O2 O -0.0507(6) 0.92039(10) 0.2422(4) 0.0634(9) Uani 1 1 d . . .
O3 O -0.2027(5) 0.73821(10) 0.1481(4) 0.0554(8) Uani 1 1 d . . .
H3 H -0.1647 0.7108 0.1588 0.083 Uiso 1 1 calc R . .
S1 S 0.43024(18) 0.67359(4) 0.41596(15) 0.0491(4) Uani 1 1 d . . .
C1 C 0.4166(8) 0.86350(15) 0.4290(6) 0.0490(10) Uani 1 1 d . . .
C2 C 0.0871(8) 0.89238(15) 0.2963(6) 0.0516(11) Uani 1 1 d . . .
C3 C 0.0808(7) 0.84136(14) 0.2850(5) 0.0440(10) Uani 1 1 d . . .
C4 C 0.2765(7) 0.82398(14) 0.3669(5) 0.0433(10) Uani 1 1 d . . .
C5 C 0.3155(7) 0.77752(14) 0.3767(5) 0.0452(10) Uani 1 1 d . . .
H5 H 0.4478 0.7661 0.4328 0.054 Uiso 1 1 calc R . .
C6 C 0.1580(7) 0.74745(14) 0.3031(5) 0.0400(9) Uani 1 1 d . . .
C7 C -0.0426(7) 0.76501(14) 0.2207(5) 0.0438(10) Uani 1 1 d . . .
C8 C -0.0793(7) 0.81291(15) 0.2136(5) 0.0480(11) Uani 1 1 d . . .
H8 H -0.2122 0.8250 0.1604 0.058 Uiso 1 1 calc R . .
C9 C 0.1887(7) 0.69761(14) 0.3161(5) 0.0416(10) Uani 1 1 d . . .
C10 C 0.1001(7) 0.62291(14) 0.2999(5) 0.0439(10) Uani 1 1 d . . .
C11 C 0.3137(7) 0.61954(14) 0.3866(5) 0.0449(10) Uani 1 1 d . . .
C12 C 0.4001(8) 0.57646(15) 0.4352(6) 0.0538(12) Uani 1 1 d . . .
H12 H 0.5423 0.5738 0.4931 0.065 Uiso 1 1 calc R . .
C13 C 0.2713(8) 0.53847(16) 0.3957(6) 0.0598(12) Uani 1 1 d . . .
H13 H 0.3256 0.5093 0.4289 0.072 Uiso 1 1 calc R . .
C14 C 0.0626(9) 0.54148(16) 0.3080(6) 0.0628(13) Uani 1 1 d . . .
H14 H -0.0198 0.5144 0.2816 0.075 Uiso 1 1 calc R . .
C15 C -0.0256(8) 0.58353(15) 0.2592(6) 0.0563(12) Uani 1 1 d . . .
H15 H -0.1671 0.5855 0.2000 0.068 Uiso 1 1 calc R . .
C16 C 0.3796(9) 0.94958(15) 0.4132(7) 0.0694(14) Uani 1 1 d . . .
H16A H 0.3551 0.9569 0.5309 0.104 Uiso 1 1 calc R . .
H16B H 0.2947 0.9714 0.3437 0.104 Uiso 1 1 calc R . .
H16C H 0.5446 0.9515 0.3876 0.104 Uiso 1 1 calc R . .


_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
N1 C1 1.378(5) . ?
N1 C2 1.385(6) . ?
N1 C16 1.448(5) . ?
N2 C9 1.278(5) . ?
N2 C10 1.376(5) . ?
O1 C1 1.182(5) . ?
O2 C2 1.200(5) . ?
O3 C7 1.320(5) . ?
O3 H3 0.8200 . ?
S1 C11 1.702(4) . ?
S1 C9 1.723(4) . ?
C1 C4 1.469(6) . ?
C2 C3 1.468(6) . ?
C3 C8 1.344(6) . ?
C3 C4 1.377(6) . ?
C4 C5 1.354(5) . ?
C5 C6 1.371(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(5) . ?
C6 C9 1.444(6) . ?
C7 C8 1.392(6) . ?
C8 H8 0.9300 . ?
C10 C15 1.374(6) . ?
C10 C11 1.394(6) . ?
C11 C12 1.384(6) . ?
C12 C13 1.349(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C1 N1 C2 112.4(4) . . ?
C1 N1 C16 122.9(4) . . ?
C2 N1 C16 124.6(4) . . ?
C9 N2 C10 112.4(3) . . ?
C7 O3 H3 109.5 . . ?
C11 S1 C9 89.6(2) . . ?
O1 C1 N1 125.0(4) . . ?
O1 C1 C4 129.4(4) . . ?
N1 C1 C4 105.6(4) . . ?
O2 C2 N1 125.4(4) . . ?
O2 C2 C3 129.2(4) . . ?
N1 C2 C3 105.4(4) . . ?
C8 C3 C4 121.3(4) . . ?
C8 C3 C2 130.4(4) . . ?
C4 C3 C2 108.3(4) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 C1 130.8(4) . . ?
C3 C4 C1 108.2(4) . . ?
C4 C5 C6 119.3(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 119.8(4) . . ?
C5 C6 C9 121.0(4) . . ?
C7 C6 C9 119.1(4) . . ?
O3 C7 C8 117.1(4) . . ?
O3 C7 C6 123.3(4) . . ?
C8 C7 C6 119.7(4) . . ?
C3 C8 C7 118.8(4) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
N2 C9 C6 123.5(4) . . ?
N2 C9 S1 114.8(3) . . ?
C6 C9 S1 121.6(3) . . ?
C15 C10 N2 126.2(4) . . ?
C15 C10 C11 120.5(4) . . ?
N2 C10 C11 113.2(4) . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 S1 129.7(3) . . ?
C10 C11 S1 109.9(3) . . ?
C13 C12 C11 117.8(4) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C14 122.1(4) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 120.9(5) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 118.2(4) . . ?
C14 C15 H15 120.9 . . ?
C10 C15 H15 120.9 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C2 N1 C1 O1 -176.6(4) . . . . ?
C16 N1 C1 O1 2.6(7) . . . . ?
C2 N1 C1 C4 2.2(5) . . . . ?
C16 N1 C1 C4 -178.6(4) . . . . ?
C1 N1 C2 O2 179.2(4) . . . . ?
C16 N1 C2 O2 0.1(7) . . . . ?
C1 N1 C2 C3 -3.1(5) . . . . ?
C16 N1 C2 C3 177.8(4) . . . . ?
O2 C2 C3 C8 -0.7(8) . . . . ?
N1 C2 C3 C8 -178.3(4) . . . . ?
O2 C2 C3 C4 -179.7(5) . . . . ?
N1 C2 C3 C4 2.7(5) . . . . ?
C8 C3 C4 C5 0.7(7) . . . . ?
C2 C3 C4 C5 179.7(4) . . . . ?
C8 C3 C4 C1 179.5(4) . . . . ?
C2 C3 C4 C1 -1.5(5) . . . . ?
O1 C1 C4 C5 -3.0(8) . . . . ?
N1 C1 C4 C5 178.3(4) . . . . ?
O1 C1 C4 C3 178.3(5) . . . . ?
N1 C1 C4 C3 -0.4(5) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C1 C4 C5 C6 -178.2(4) . . . . ?
C4 C5 C6 C7 -0.8(6) . . . . ?
C4 C5 C6 C9 -177.7(4) . . . . ?
C5 C6 C7 O3 -179.5(4) . . . . ?
C9 C6 C7 O3 -2.6(6) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C9 C6 C7 C8 177.3(4) . . . . ?
C4 C3 C8 C7 -1.2(6) . . . . ?
C2 C3 C8 C7 -180.0(4) . . . . ?
O3 C7 C8 C3 -179.5(4) . . . . ?
C6 C7 C8 C3 0.6(6) . . . . ?
C10 N2 C9 C6 -176.0(4) . . . . ?
C10 N2 C9 S1 1.0(5) . . . . ?
C5 C6 C9 N2 173.8(4) . . . . ?
C7 C6 C9 N2 -3.1(6) . . . . ?
C5 C6 C9 S1 -2.9(5) . . . . ?
C7 C6 C9 S1 -179.9(3) . . . . ?
C11 S1 C9 N2 -1.2(3) . . . . ?
C11 S1 C9 C6 175.8(3) . . . . ?
C9 N2 C10 C15 -179.9(4) . . . . ?
C9 N2 C10 C11 -0.1(5) . . . . ?
C15 C10 C11 C12 -1.0(6) . . . . ?
N2 C10 C11 C12 179.2(4) . . . . ?
C15 C10 C11 S1 179.0(3) . . . . ?
N2 C10 C11 S1 -0.8(5) . . . . ?
C9 S1 C11 C12 -178.9(4) . . . . ?
C9 S1 C11 C10 1.1(3) . . . . ?
C10 C11 C12 C13 0.0(7) . . . . ?
S1 C11 C12 C13 -180.0(4) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C12 C13 C14 C15 -1.0(8) . . . . ?
C13 C14 C15 C10 0.1(7) . . . . ?
N2 C10 C15 C14 -179.3(4) . . . . ?
C11 C10 C15 C14 0.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.059
