# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_r2
_database_code_depnum_ccdc_archive 'CCDC 1451828'
_audit_update_record             
;
2016-02-04 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N3 O2 S'
_chemical_formula_weight         347.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   9.6224(12)
_cell_length_b                   14.7044(19)
_cell_length_c                   11.8502(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.565(4)
_cell_angle_gamma                90.00
_cell_volume                     1658.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2729
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      64.53

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6109
_exptl_absorpt_correction_T_max  0.6501
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       '\\\f and \\\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16278
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.65
_diffrn_reflns_theta_max         64.53
_reflns_number_total             2729
_reflns_number_gt                2603
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0488P)²+0.4828P] 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         2729
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.53180(13) 0.65529(8) 0.73103(11) 0.0413(3) Uani 1 1 d . . .
C2 C 0.61794(16) 0.66885(10) 0.83189(13) 0.0383(3) Uani 1 1 d . . .
C3 C 0.61782(15) 0.75974(10) 0.86359(12) 0.0359(3) Uani 1 1 d . . .
C4 C 0.68256(17) 0.81225(11) 0.95620(13) 0.0437(4) Uani 1 1 d . . .
H4 H 0.7457 0.7857 1.0138 0.052 Uiso 1 1 calc R . .
C5 C 0.65151(19) 0.90231(11) 0.96031(15) 0.0495(4) Uani 1 1 d . . .
H5 H 0.6946 0.9378 1.0205 0.059 Uiso 1 1 calc R . .
C6 C 0.55366(19) 0.94237(11) 0.87308(15) 0.0492(4) Uani 1 1 d . . .
H6 H 0.5316 1.0037 0.8777 0.059 Uiso 1 1 calc R . .
C7 C 0.49256(17) 0.89305(10) 0.78408(14) 0.0437(4) Uani 1 1 d . . .
H7 H 0.4282 0.9200 0.7276 0.052 Uiso 1 1 calc R . .
N8 N 0.52583(13) 0.80180(8) 0.77684(10) 0.0358(3) Uani 1 1 d . . .
C9 C 0.47810(16) 0.73554(10) 0.69804(13) 0.0387(3) Uani 1 1 d . . .
C10 C 0.38214(16) 0.75019(11) 0.59136(13) 0.0433(4) Uani 1 1 d . . .
C11 C 0.3836(2) 0.82824(13) 0.52518(15) 0.0530(4) Uani 1 1 d . . .
H11 H 0.4445 0.8757 0.5499 0.064 Uiso 1 1 calc R . .
C12 C 0.2940(2) 0.83543(17) 0.42212(17) 0.0676(6) Uani 1 1 d . . .
H12 H 0.2946 0.8880 0.3785 0.081 Uiso 1 1 calc R . .
C13 C 0.2054(3) 0.7659(2) 0.3846(2) 0.0825(7) Uani 1 1 d . . .
H13 H 0.1459 0.7712 0.3155 0.099 Uiso 1 1 calc R . .
C14 C 0.2038(2) 0.68793(19) 0.4488(2) 0.0805(7) Uani 1 1 d . . .
H14 H 0.1440 0.6404 0.4223 0.097 Uiso 1 1 calc R . .
C15 C 0.2903(2) 0.67985(14) 0.55182(17) 0.0595(5) Uani 1 1 d . . .
H15 H 0.2875 0.6274 0.5952 0.071 Uiso 1 1 calc R . .
S16 S 0.70204(4) 0.58004(2) 0.91196(3) 0.04398(16) Uani 1 1 d . . .
C17 C 0.83794(15) 0.54808(10) 0.83424(13) 0.0374(3) Uani 1 1 d . . .
C18 C 0.88013(17) 0.60040(11) 0.74824(15) 0.0468(4) Uani 1 1 d . . .
H18 H 0.8353 0.6553 0.7280 0.056 Uiso 1 1 calc R . .
C19 C 0.9886(2) 0.57155(13) 0.69226(17) 0.0561(5) Uani 1 1 d . . .
H19 H 1.0155 0.6073 0.6344 0.067 Uiso 1 1 calc R . .
C20 C 1.05771(19) 0.49053(13) 0.72090(16) 0.0529(4) Uani 1 1 d . . .
H20 H 1.1316 0.4714 0.6843 0.064 Uiso 1 1 calc R . .
C21 C 1.01286(16) 0.43920(10) 0.80575(14) 0.0418(4) Uani 1 1 d . . .
C22 C 0.90469(16) 0.46508(10) 0.86309(13) 0.0395(3) Uani 1 1 d . . .
H22 H 0.8769 0.4283 0.9195 0.047 Uiso 1 1 calc R . .
N23 N 1.08035(16) 0.35069(10) 0.83538(13) 0.0521(4) Uani 1 1 d . . .
O24 O 1.19007(17) 0.33366(11) 0.79980(14) 0.0794(5) Uani 1 1 d . . .
O25 O 1.02426(16) 0.29838(9) 0.89341(15) 0.0722(4) Uani 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
N1 C9 1.324(2) . ?
N1 C2 1.364(2) . ?
C2 C3 1.388(2) . ?
C2 S16 1.7412(15) . ?
C3 N8 1.3969(19) . ?
C3 C4 1.409(2) . ?
C4 C5 1.360(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.418(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.341(2) . ?
C6 H6 0.9300 . ?
C7 N8 1.3851(19) . ?
C7 H7 0.9300 . ?
N8 C9 1.380(2) . ?
C9 C10 1.466(2) . ?
C10 C11 1.391(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
S16 C17 1.7715(16) . ?
C17 C18 1.385(2) . ?
C17 C22 1.398(2) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(2) . ?
C21 N23 1.473(2) . ?
C22 H22 0.9300 . ?
N23 O25 1.211(2) . ?
N23 O24 1.220(2) . ?

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
C9 N1 C2 106.75(12) . . ?
N1 C2 C3 110.66(12) . . ?
N1 C2 S16 122.71(11) . . ?
C3 C2 S16 126.42(12) . . ?
C2 C3 N8 104.66(12) . . ?
C2 C3 C4 136.07(14) . . ?
N8 C3 C4 119.26(13) . . ?
C5 C4 C3 119.17(15) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.25(15) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.94(15) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 N8 119.61(15) . . ?
C6 C7 H7 120.2 . . ?
N8 C7 H7 120.2 . . ?
C9 N8 C7 132.00(13) . . ?
C9 N8 C3 107.21(12) . . ?
C7 N8 C3 120.68(13) . . ?
N1 C9 N8 110.70(13) . . ?
N1 C9 C10 123.62(14) . . ?
N8 C9 C10 125.67(13) . . ?
C11 C10 C15 118.76(16) . . ?
C11 C10 C9 123.33(16) . . ?
C15 C10 C9 117.82(16) . . ?
C12 C11 C10 120.08(19) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C2 S16 C17 103.58(7) . . ?
C18 C17 C22 119.38(15) . . ?
C18 C17 S16 123.72(12) . . ?
C22 C17 S16 116.90(12) . . ?
C19 C18 C17 120.46(15) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 121.07(16) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 117.41(16) . . ?
C21 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
C20 C21 C22 123.39(15) . . ?
C20 C21 N23 118.90(15) . . ?
C22 C21 N23 117.69(15) . . ?
C21 C22 C17 118.27(14) . . ?
C21 C22 H22 120.9 . . ?
C17 C22 H22 120.9 . . ?
O25 N23 O24 123.22(15) . . ?
O25 N23 C21 118.59(15) . . ?
O24 N23 C21 118.19(16) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        64.53
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.036
