# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_crs_apr22_0m
_database_code_depnum_ccdc_archive 'CCDC 1405369'
_audit_update_record             
;
2015-06-06 deposited with the CCDC.
2015-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N3 O4 S'
_chemical_formula_weight         407.44

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3710(5)
_cell_length_b                   10.0074(6)
_cell_length_c                   12.8160(8)
_cell_angle_alpha                67.264(4)
_cell_angle_beta                 80.722(5)
_cell_angle_gamma                86.904(5)
_cell_volume                     977.20(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.982
_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            13194
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3316
_reflns_number_gt                1823
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0805P)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         3316
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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 -0.18705(13) -0.17043(10) 0.41309(8) 0.0627(4) Uani 1 1 d . . .
O1 O -0.4216(4) 0.2965(3) 0.2739(3) 0.1065(11) Uani 1 1 d . . .
O2 O -0.2243(4) -0.3121(3) 0.4225(2) 0.0843(9) Uani 1 1 d . . .
O3 O -0.1526(3) -0.1470(3) 0.51074(19) 0.0728(8) Uani 1 1 d . . .
O4 O 0.4208(4) 0.1344(3) -0.1884(2) 0.0738(8) Uani 1 1 d . . .
N1 N -0.4297(5) 0.1583(4) 0.2709(4) 0.1034(13) Uani 1 1 d . . .
N2 N -0.3431(4) -0.0725(4) 0.3688(3) 0.0603(9) Uani 1 1 d . . .
N3 N 0.3272(4) 0.0972(3) 0.0195(2) 0.0557(8) Uani 1 1 d . . .
C1 C -0.3134(6) 0.4240(4) 0.3701(4) 0.1050(17) Uani 1 1 d . . .
H1A H -0.3663 0.5010 0.3158 0.157 Uiso 1 1 calc R . .
H1B H -0.1999 0.4459 0.3576 0.157 Uiso 1 1 calc R . .
H1C H -0.3596 0.4141 0.4463 0.157 Uiso 1 1 calc R . .
C2 C -0.3355(5) 0.2862(5) 0.3554(4) 0.0696(11) Uani 1 1 d . . .
C3 C -0.2898(5) 0.1512(4) 0.4047(3) 0.0701(12) Uani 1 1 d . . .
H3 H -0.2290 0.1144 0.4643 0.084 Uiso 1 1 calc R . .
C4 C -0.3511(5) 0.0755(4) 0.3495(3) 0.0576(10) Uani 1 1 d . . .
C5 C -0.0264(4) -0.0990(4) 0.3024(3) 0.0513(9) Uani 1 1 d . . .
C6 C -0.0112(5) -0.1336(4) 0.2056(3) 0.0557(10) Uani 1 1 d . . .
H6 H -0.0811 -0.2007 0.2026 0.067 Uiso 1 1 calc R . .
C7 C 0.1076(4) -0.0676(4) 0.1151(3) 0.0573(10) Uani 1 1 d . . .
H7 H 0.1163 -0.0894 0.0501 0.069 Uiso 1 1 calc R . .
C8 C 0.2145(4) 0.0304(4) 0.1181(3) 0.0512(9) Uani 1 1 d . . .
C9 C 0.2043(5) 0.0611(4) 0.2161(3) 0.0588(10) Uani 1 1 d . . .
H9 H 0.2784 0.1238 0.2208 0.071 Uiso 1 1 calc R . .
C10 C 0.0827(5) -0.0030(4) 0.3061(3) 0.0590(10) Uani 1 1 d . . .
H10 H 0.0740 0.0189 0.3710 0.071 Uiso 1 1 calc R . .
C11 C 0.4396(5) 0.1941(4) 0.0047(3) 0.0590(11) Uani 1 1 d . . .
C12 C 0.5391(4) 0.2627(4) -0.0982(3) 0.0563(10) Uani 1 1 d . . .
C13 C 0.5227(5) 0.2293(4) -0.1965(3) 0.0611(10) Uani 1 1 d . . .
C14 C 0.6223(5) 0.3038(5) -0.3010(3) 0.0759(12) Uani 1 1 d . . .
H14 H 0.6143 0.2811 -0.3639 0.091 Uiso 1 1 calc R . .
C15 C 0.7280(6) 0.4060(5) -0.3128(4) 0.0846(13) Uani 1 1 d . . .
H15 H 0.7883 0.4543 -0.3844 0.101 Uiso 1 1 calc R . .
C16 C 0.7519(5) 0.4440(4) -0.2196(4) 0.0709(12) Uani 1 1 d . . .
C17 C 0.8650(6) 0.5489(5) -0.2332(5) 0.0914(15) Uani 1 1 d . . .
H17 H 0.9250 0.5971 -0.3049 0.110 Uiso 1 1 calc R . .
C18 C 0.8894(6) 0.5825(5) -0.1432(6) 0.0995(17) Uani 1 1 d . . .
H18 H 0.9664 0.6517 -0.1533 0.119 Uiso 1 1 calc R . .
C19 C 0.7988(6) 0.5129(5) -0.0377(5) 0.0939(15) Uani 1 1 d . . .
H19 H 0.8148 0.5359 0.0236 0.113 Uiso 1 1 calc R . .
C20 C 0.6864(5) 0.4112(5) -0.0215(4) 0.0781(12) Uani 1 1 d . . .
H20 H 0.6265 0.3661 0.0508 0.094 Uiso 1 1 calc R . .
C21 C 0.6582(4) 0.3723(4) -0.1111(3) 0.0606(10) Uani 1 1 d . . .
H1N2 H -0.379(4) -0.099(4) 0.327(3) 0.061(12) Uiso 1 1 d . . .
H11 H 0.452(4) 0.213(3) 0.062(3) 0.049(10) Uiso 1 1 d . . .
H1O4 H 0.369(12) 0.098(10) -0.116(4) 0.105(6) 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 O2 1.423(2) . ?
S1 O3 1.433(2) . ?
S1 N2 1.631(3) . ?
S1 C5 1.742(4) . ?
O1 C2 1.332(4) . ?
O1 N1 1.403(4) . ?
O4 C13 1.274(4) . ?
O4 H1O4 0.90(2) . ?
N1 C4 1.281(5) . ?
N2 C4 1.404(5) . ?
N2 H1N2 0.79(3) . ?
N3 C11 1.327(4) . ?
N3 C8 1.402(4) . ?
C1 C2 1.486(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.317(5) . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C5 C10 1.380(4) . ?
C5 C6 1.397(4) . ?
C6 C7 1.371(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(5) . ?
C9 C10 1.378(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.383(5) . ?
C11 H11 0.85(3) . ?
C12 C13 1.450(5) . ?
C12 C21 1.466(5) . ?
C13 C14 1.407(5) . ?
C14 C15 1.337(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.431(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(5) . ?
C16 C21 1.415(5) . ?
C17 C18 1.366(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.358(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.403(5) . ?
C20 H20 0.9300 . ?

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
O2 S1 O3 120.31(16) . . ?
O2 S1 N2 105.16(18) . . ?
O3 S1 N2 108.10(17) . . ?
O2 S1 C5 109.08(17) . . ?
O3 S1 C5 107.93(17) . . ?
N2 S1 C5 105.28(16) . . ?
C2 O1 N1 107.8(3) . . ?
C13 O4 H1O4 108(7) . . ?
C4 N1 O1 105.4(3) . . ?
C4 N2 S1 122.0(3) . . ?
C4 N2 H1N2 119(3) . . ?
S1 N2 H1N2 110(3) . . ?
C11 N3 C8 126.8(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 109.5(4) . . ?
C3 C2 C1 135.2(4) . . ?
O1 C2 C1 115.2(4) . . ?
C2 C3 C4 105.6(4) . . ?
C2 C3 H3 127.2 . . ?
C4 C3 H3 127.2 . . ?
N1 C4 C3 111.6(4) . . ?
N1 C4 N2 118.1(4) . . ?
C3 C4 N2 130.3(4) . . ?
C10 C5 C6 119.0(3) . . ?
C10 C5 S1 121.1(3) . . ?
C6 C5 S1 119.9(3) . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 N3 117.3(3) . . ?
C9 C8 N3 123.2(3) . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C5 121.6(3) . . ?
C9 C10 H10 119.2 . . ?
C5 C10 H10 119.2 . . ?
N3 C11 C12 123.3(4) . . ?
N3 C11 H11 118(2) . . ?
C12 C11 H11 119(2) . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 C21 121.3(3) . . ?
C13 C12 C21 119.0(4) . . ?
O4 C13 C14 120.7(4) . . ?
O4 C13 C12 120.8(4) . . ?
C14 C13 C12 118.6(4) . . ?
C15 C14 C13 122.1(4) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 122.6(4) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C17 C16 C21 119.6(4) . . ?
C17 C16 C15 121.7(5) . . ?
C21 C16 C15 118.7(4) . . ?
C18 C17 C16 121.3(5) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 121.0(5) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 121.7(5) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C20 C21 C16 117.1(4) . . ?
C20 C21 C12 123.9(4) . . ?
C16 C21 C12 119.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
