# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2021

####################################################################### 
# 
# 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_c16h18
_database_code_depnum_ccdc_archive 'CCDC 2068464'
loop_
_audit_author_name
_audit_author_address
'Kuangsen Sung'
;National Cheng Kung University
Taiwan
;
_audit_update_record             
;
2021-07-01 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H18 N4 O3 S'
_chemical_formula_sum            'C16 H18 N4 O3 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         346.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   10.7329(4)
_cell_length_b                   15.3130(6)
_cell_length_c                   10.9752(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.0676(16)
_cell_angle_gamma                90
_cell_volume                     1683.23(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      3.322
_cell_measurement_theta_max      27.061
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8340
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28452
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.322
_diffrn_reflns_theta_max         27.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3718
_reflns_number_gt                2836
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+1.4827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3718
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.001
_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_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
S S 0.55935(6) 0.08125(4) 0.79384(6) 0.03084(17) Uani 1 1 d . . . . .
O1 O 0.15180(15) 0.05632(12) 0.22910(15) 0.0322(4) Uani 1 1 d . . . . .
O2 O 0.40821(16) -0.17076(11) 0.56461(18) 0.0359(4) Uani 1 1 d . . . . .
O3 O 0.61781(16) -0.17254(11) 0.56193(17) 0.0348(4) Uani 1 1 d . . . . .
N1 N -0.03418(18) 0.14301(13) 0.19317(17) 0.0265(4) Uani 1 1 d . . . . .
N2 N -0.04246(18) 0.15289(12) 0.39528(18) 0.0266(4) Uani 1 1 d . . . . .
N3 N 0.36374(18) -0.03483(13) 0.69343(18) 0.0236(4) Uani 1 1 d . . . . .
H3A H 0.338(3) -0.0795(19) 0.646(3) 0.036(8) Uiso 1 1 d . . . . .
N4 N 0.56247(19) -0.06386(12) 0.66492(18) 0.0244(4) Uani 1 1 d . . . . .
H4A H 0.640(3) -0.0523(16) 0.686(2) 0.023(6) Uiso 1 1 d . . . . .
C1 C 0.0732(2) 0.09434(15) 0.2684(2) 0.0248(5) Uani 1 1 d . . . . .
C2 C -0.0977(2) 0.17525(15) 0.2735(2) 0.0266(5) Uani 1 1 d . . . . .
C3 C 0.0672(2) 0.10038(15) 0.4014(2) 0.0236(4) Uani 1 1 d . . . . .
C4 C 0.1569(2) 0.06017(15) 0.5047(2) 0.0245(5) Uani 1 1 d . . . . .
H4B H 0.2231 0.0273 0.4862 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1675(2) 0.05961(14) 0.6408(2) 0.0235(4) Uani 1 1 d . . . . .
C6 C 0.0768(2) 0.10368(16) 0.6844(2) 0.0303(5) Uani 1 1 d . . . . .
H6A H 0.0058 0.1359 0.6238 0.036 Uiso 1 1 calc R U . . .
C7 C 0.0892(3) 0.10091(17) 0.8138(2) 0.0337(5) Uani 1 1 d . . . . .
H7A H 0.0265 0.1310 0.8413 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1923(2) 0.05456(16) 0.9041(2) 0.0315(5) Uani 1 1 d . . . . .
H8A H 0.1999 0.0526 0.9930 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2842(2) 0.01111(15) 0.8641(2) 0.0270(5) Uani 1 1 d . . . . .
H9A H 0.3555 -0.0204 0.9256 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2717(2) 0.01378(14) 0.7339(2) 0.0231(4) Uani 1 1 d . . . . .
C11 C 0.4893(2) -0.00939(14) 0.71471(19) 0.0229(4) Uani 1 1 d . . . . .
C12 C 0.5193(2) -0.13991(15) 0.5941(2) 0.0267(5) Uani 1 1 d . . . . .
C13 C 0.5880(3) -0.25282(19) 0.4845(3) 0.0496(8) Uani 1 1 d . . . . .
H13A H 0.4962 -0.2504 0.4190 0.060 Uiso 1 1 calc R U . . .
H13B H 0.5945 -0.3038 0.5419 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6858(3) -0.26154(18) 0.4178(3) 0.0415(6) Uani 1 1 d . . . . .
H14A H 0.6672 -0.3151 0.3654 0.062 Uiso 1 1 calc R U . . .
H14B H 0.6784 -0.2110 0.3608 0.062 Uiso 1 1 calc R U . . .
H14C H 0.7764 -0.2643 0.4833 0.062 Uiso 1 1 calc R U . . .
C15 C -0.0746(3) 0.1530(2) 0.0516(2) 0.0374(6) Uani 1 1 d . . . . .
H15A H -0.1537 0.1905 0.0193 0.19(3) Uiso 1 1 calc R . . . .
H15B H -0.0015 0.1796 0.0309 0.14(2) Uiso 1 1 calc R . . . .
H15C H -0.0956 0.0955 0.0099 0.14(2) Uiso 1 1 calc R . . . .
C16 C -0.2193(3) 0.23051(19) 0.2197(3) 0.0394(6) Uani 1 1 d . . . . .
H16A H -0.2415 0.2382 0.1256 0.22(3) Uiso 1 1 calc R . . . .
H16B H -0.2940 0.2020 0.2353 0.25(4) Uiso 1 1 calc R . . . .
H16C H -0.2025 0.2877 0.2627 0.28(4) 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
S C11 1.666(2) . ?
O1 C1 1.224(3) . ?
O2 C12 1.213(3) . ?
O3 C12 1.327(3) . ?
O3 C13 1.463(3) . ?
N1 C1 1.372(3) . ?
N1 C2 1.385(3) . ?
N1 C15 1.463(3) . ?
N2 C2 1.298(3) . ?
N2 C3 1.406(3) . ?
N3 C11 1.340(3) . ?
N3 C10 1.429(3) . ?
N3 H3A 0.84(3) . ?
N4 C12 1.384(3) . ?
N4 C11 1.385(3) . ?
N4 H4A 0.80(3) . ?
C1 C3 1.488(3) . ?
C2 C16 1.488(3) . ?
C3 C4 1.344(3) . ?
C4 C5 1.457(3) . ?
C4 H4B 0.9500 . ?
C5 C10 1.402(3) . ?
C5 C6 1.402(3) . ?
C6 C7 1.379(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.386(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.386(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9A 0.9500 . ?
C13 C14 1.485(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C12 O3 C13 116.25(18) . . ?
C1 N1 C2 108.06(17) . . ?
C1 N1 C15 124.05(19) . . ?
C2 N1 C15 127.8(2) . . ?
C2 N2 C3 105.37(18) . . ?
C11 N3 C10 123.97(19) . . ?
C11 N3 H3A 115.0(18) . . ?
C10 N3 H3A 120.6(19) . . ?
C12 N4 C11 127.24(19) . . ?
C12 N4 H4A 116.9(18) . . ?
C11 N4 H4A 115.6(18) . . ?
O1 C1 N1 125.6(2) . . ?
O1 C1 C3 130.9(2) . . ?
N1 C1 C3 103.47(18) . . ?
N2 C2 N1 114.46(19) . . ?
N2 C2 C16 124.8(2) . . ?
N1 C2 C16 120.8(2) . . ?
C4 C3 N2 129.50(19) . . ?
C4 C3 C1 121.87(19) . . ?
N2 C3 C1 108.63(18) . . ?
C3 C4 C5 129.5(2) . . ?
C3 C4 H4B 115.3 . . ?
C5 C4 H4B 115.3 . . ?
C10 C5 C6 117.52(19) . . ?
C10 C5 C4 119.89(19) . . ?
C6 C5 C4 122.6(2) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C5 121.5(2) . . ?
C9 C10 N3 118.9(2) . . ?
C5 C10 N3 119.57(18) . . ?
N3 C11 N4 115.7(2) . . ?
N3 C11 S 124.74(17) . . ?
N4 C11 S 119.58(16) . . ?
O2 C12 O3 125.7(2) . . ?
O2 C12 N4 125.2(2) . . ?
O3 C12 N4 109.15(18) . . ?
O3 C13 C14 108.4(2) . . ?
O3 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
O3 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.066


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

