# 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_km
_database_code_depnum_ccdc_archive 'CCDC 1053279'
_audit_update_record             
;
2015-03-11 deposited with the CCDC.
2016-02-16 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 H12 N2 O3 S'
_chemical_formula_weight         347.27

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           Mnonclinic
_symmetry_space_group_name_H-M   'P 21/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                   12.513(5)
_cell_length_b                   14.980(6)
_cell_length_c                   8.251(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.583(14)
_cell_angle_gamma                90.00
_cell_volume                     1545.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    16744
_cell_measurement_theta_min      1.63
_cell_measurement_theta_max      24.82

_exptl_crystal_description       Needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16744
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         24.82
_reflns_number_total             2650
_reflns_number_gt                1880
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'

_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)+(0.2000P)²+0.0000P] 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         2650
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1477
_refine_ls_R_factor_gt           0.1220
_refine_ls_wR_factor_ref         0.3787
_refine_ls_wR_factor_gt          0.3602
_refine_ls_goodness_of_fit_ref   1.488
_refine_ls_restrained_S_all      1.488
_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
S1 S 0.29289(17) 0.36044(12) 0.8376(2) 0.0721(8) Uani 1 1 d . . .
O1 O 0.9093(5) 0.3312(4) 0.2400(7) 0.0862(17) Uani 1 1 d . . .
O2 O 0.6648(4) 0.0854(3) 0.5186(6) 0.0649(13) Uani 1 1 d . . .
N1 N 0.5289(4) 0.2243(3) 0.6306(5) 0.0445(12) Uani 1 1 d . . .
C1 C 0.2029(6) 0.2914(6) 0.9181(9) 0.078(2) Uani 1 1 d . . .
H1 H 0.1418 0.3114 0.9670 0.093 Uiso 1 1 calc R . .
C2 C 0.3685(5) 0.2712(4) 0.7777(7) 0.0511(15) Uani 1 1 d . . .
C3 C 0.4632(5) 0.2886(4) 0.6888(7) 0.0479(15) Uani 1 1 d . . .
C4 C 0.6076(5) 0.2673(3) 0.5493(6) 0.0436(14) Uani 1 1 d . . .
C5 C 0.6962(5) 0.2367(3) 0.4673(6) 0.0434(14) Uani 1 1 d . . .
C6 C 0.7208(5) 0.1412(3) 0.4550(7) 0.0458(14) Uani 1 1 d . . .
C7 C 0.8164(5) 0.1154(4) 0.3647(7) 0.0525(15) Uani 1 1 d . . .
C8 C 0.8790(5) 0.1794(4) 0.2927(8) 0.0543(16) Uani 1 1 d . . .
C9 C 0.9673(6) 0.1518(5) 0.2100(9) 0.0685(19) Uani 1 1 d . . .
H9 H 1.0099 0.1940 0.1611 0.082 Uiso 1 1 calc R . .
C10 C 0.9925(7) 0.0626(6) 0.1999(10) 0.083(2) Uani 1 1 d . . .
H10 H 1.0515 0.0450 0.1434 0.100 Uiso 1 1 calc R . .
C11 C 0.7591(5) 0.3020(4) 0.3955(7) 0.0517(15) Uani 1 1 d . . .
C12 C 0.8539(5) 0.2754(4) 0.3056(7) 0.0593(17) Uani 1 1 d . . .
C13 C 0.8427(6) 0.0251(4) 0.3525(9) 0.0680(19) Uani 1 1 d . . .
H13 H 0.8001 -0.0179 0.3990 0.082 Uiso 1 1 calc R . .
C14 C 0.9317(7) -0.0002(6) 0.2719(10) 0.087(2) Uani 1 1 d . . .
H14 H 0.9503 -0.0601 0.2664 0.104 Uiso 1 1 calc R . .
C15 C 0.7341(6) 0.3934(4) 0.4087(8) 0.0589(17) Uani 1 1 d . . .
H15 H 0.7768 0.4352 0.3593 0.071 Uiso 1 1 calc R . .
C16 C 0.6490(6) 0.4220(4) 0.4917(7) 0.0599(18) Uani 1 1 d . . .
H16 H 0.6342 0.4827 0.5003 0.072 Uiso 1 1 calc R . .
C17 C 0.5846(6) 0.3589(3) 0.5633(7) 0.0535(17) Uani 1 1 d . . .
C18 C 0.3239(6) 0.1923(4) 0.8238(7) 0.0608(18) Uani 1 1 d . . .
H18 H 0.3535 0.1366 0.8041 0.073 Uiso 1 1 calc R . .
C19 C 0.2282(6) 0.2047(5) 0.9044(8) 0.071(2) Uani 1 1 d . . .
H19 H 0.1873 0.1583 0.9436 0.086 Uiso 1 1 calc R . .
N2A N 0.4955(5) 0.3702(3) 0.6512(6) 0.054(2) Uani 0.99(2) 1 d P . .
O4 O 0.4638(4) 0.0386(3) 0.6728(7) 0.060(2) Uani 0.94(2) 1 d P . .
H100 H 0.516(5) 0.169(4) 0.630(6) 0.043(15) Uiso 1 1 d . . .
H101 H 0.479(7) -0.005(7) 0.727(11) 0.10(3) Uiso 1 1 d . . .
H102 H 0.459(9) 0.011(8) 0.581(13) 0.13(4) 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
S1 C1 1.687(8) . ?
S1 C2 1.722(6) . ?
O1 C12 1.227(8) . ?
O2 C6 1.225(7) . ?
N1 C3 1.367(7) . ?
N1 C4 1.376(7) . ?
N1 H100 0.85(6) . ?
C1 C19 1.343(11) . ?
C1 H1 0.9300 . ?
C2 C18 1.369(9) . ?
C2 C3 1.445(9) . ?
C3 N2A 1.329(7) . ?
C4 C5 1.402(8) . ?
C4 C17 1.409(7) . ?
C5 C11 1.403(8) . ?
C5 C6 1.468(7) . ?
C6 C7 1.489(9) . ?
C7 C8 1.388(9) . ?
C7 C13 1.397(9) . ?
C8 C9 1.387(10) . ?
C8 C12 1.477(9) . ?
C9 C10 1.376(11) . ?
C9 H9 0.9300 . ?
C10 C14 1.363(12) . ?
C10 H10 0.9300 . ?
C11 C15 1.409(9) . ?
C11 C12 1.482(10) . ?
C13 C14 1.375(11) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.361(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.392(9) . ?
C16 H16 0.9300 . ?
C17 N2A 1.368(9) . ?
C18 C19 1.407(10) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O4 H101 0.81(11) . ?
O4 H102 0.86(11) . ?

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 S1 C2 91.3(4) . . ?
C3 N1 C4 107.3(5) . . ?
C3 N1 H100 125(4) . . ?
C4 N1 H100 127(4) . . ?
C19 C1 S1 113.3(6) . . ?
C19 C1 H1 123.4 . . ?
S1 C1 H1 123.4 . . ?
C18 C2 C3 130.6(5) . . ?
C18 C2 S1 110.8(5) . . ?
C3 C2 S1 118.7(4) . . ?
N2A C3 N1 111.9(5) . . ?
N2A C3 C2 123.3(5) . . ?
N1 C3 C2 124.9(5) . . ?
N1 C4 C5 133.0(5) . . ?
N1 C4 C17 105.2(5) . . ?
C5 C4 C17 121.9(5) . . ?
C4 C5 C11 116.5(5) . . ?
C4 C5 C6 121.7(5) . . ?
C11 C5 C6 121.8(6) . . ?
O2 C6 C5 120.7(5) . . ?
O2 C6 C7 121.7(5) . . ?
C5 C6 C7 117.6(5) . . ?
C8 C7 C13 119.9(6) . . ?
C8 C7 C6 121.1(5) . . ?
C13 C7 C6 119.0(6) . . ?
C9 C8 C7 118.8(6) . . ?
C9 C8 C12 120.1(6) . . ?
C7 C8 C12 121.0(6) . . ?
C10 C9 C8 120.5(7) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C14 C10 C9 120.7(8) . . ?
C14 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C5 C11 C15 120.9(6) . . ?
C5 C11 C12 120.0(6) . . ?
C15 C11 C12 119.0(5) . . ?
O1 C12 C8 120.4(7) . . ?
O1 C12 C11 121.2(6) . . ?
C8 C12 C11 118.4(5) . . ?
C14 C13 C7 120.0(7) . . ?
C14 C13 H13 120.0 . . ?
C7 C13 H13 120.0 . . ?
C10 C14 C13 120.0(7) . . ?
C10 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C11 121.8(6) . . ?
C16 C15 H15 119.1 . . ?
C11 C15 H15 119.1 . . ?
C15 C16 C17 118.7(6) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
N2A C17 C16 130.0(5) . . ?
N2A C17 C4 109.9(5) . . ?
C16 C17 C4 120.2(6) . . ?
C2 C18 C19 112.5(6) . . ?
C2 C18 H18 123.7 . . ?
C19 C18 H18 123.7 . . ?
C1 C19 C18 112.1(7) . . ?
C1 C19 H19 123.9 . . ?
C18 C19 H19 123.9 . . ?
C3 N2A C17 105.8(5) . . ?
H101 O4 H102 96(9) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.82
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.125
