# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1549520'
_audit_update_record             
;
2017-05-12 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H28 N4 O6 S2'
_chemical_formula_weight         544.63

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                   10.2637(11)
_cell_length_b                   12.3231(14)
_cell_length_c                   12.7383(14)
_cell_angle_alpha                97.1560(10)
_cell_angle_beta                 107.7330(10)
_cell_angle_gamma                112.9910(10)
_cell_volume                     1357.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2604
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      22.83

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9309
_exptl_absorpt_correction_T_max  0.9623
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            10855
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.15
_reflns_number_total             4829
_reflns_number_gt                3191
_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    '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)+(0.0860P)²+0.3148P] 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         4829
_refine_ls_number_parameters     339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1439
_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 0.7810(2) 0.74041(19) 0.24417(19) 0.0422(5) Uani 1 1 d . . .
N2 N 0.9286(3) 1.0744(2) 0.2884(2) 0.0525(6) Uani 1 1 d . . .
N3 N 0.6439(3) 0.8492(2) 0.1876(2) 0.0464(6) Uani 1 1 d . . .
H3 H 0.5767 0.7842 0.1328 0.056 Uiso 1 1 calc R . .
N4 N 1.2624(3) 0.8141(3) 0.5200(3) 0.0810(9) Uani 1 1 d . . .
O1 O 0.5467(3) 0.3156(2) 0.04222(19) 0.0769(7) Uani 1 1 d . . .
O2 O 0.9011(2) 0.62711(19) 0.3115(2) 0.0660(6) Uani 1 1 d . . .
O3 O 0.8903(3) 1.0789(2) 0.1881(2) 0.0745(7) Uani 1 1 d . . .
O4 O 0.9797(3) 1.1628(2) 0.3698(2) 0.0729(7) Uani 1 1 d . . .
O5 O 0.1577(3) 0.4611(3) 0.3284(2) 0.0930(9) Uani 1 1 d . . .
O6 O -0.0428(2) 0.7568(2) 0.0811(2) 0.0647(6) Uani 1 1 d . . .
S1 S 1.21885(9) 1.09372(8) 0.45331(8) 0.0693(3) Uani 1 1 d . . .
S2 S 0.63140(12) 0.26205(8) 0.11568(8) 0.0750(3) Uani 1 1 d . . .
C1 C 0.6432(8) 0.3150(5) 0.2559(4) 0.148(3) Uani 1 1 d . . .
H1A H 0.6928 0.4031 0.2793 0.221 Uiso 1 1 calc R . .
H1B H 0.7015 0.2855 0.3082 0.221 Uiso 1 1 calc R . .
H1C H 0.5418 0.2851 0.2560 0.221 Uiso 1 1 calc R . .
C2 C 0.8255(5) 0.3494(4) 0.1395(5) 0.130(2) Uani 1 1 d . . .
H2A H 0.8410 0.3310 0.0701 0.195 Uiso 1 1 calc R . .
H2B H 0.8885 0.3298 0.1990 0.195 Uiso 1 1 calc R . .
H2C H 0.8528 0.4351 0.1624 0.195 Uiso 1 1 calc R . .
C3 C 1.0491(3) 0.9545(3) 0.3781(2) 0.0453(7) Uani 1 1 d . . .
C4 C 1.0440(3) 0.8422(3) 0.3821(2) 0.0483(7) Uani 1 1 d . . .
C5 C 0.9091(3) 0.7287(3) 0.3118(3) 0.0486(7) Uani 1 1 d . . .
C6 C 0.7781(3) 0.8509(2) 0.2454(2) 0.0423(6) Uani 1 1 d . . .
C7 C 0.9160(3) 0.9584(2) 0.3099(2) 0.0436(7) Uani 1 1 d . . .
C8 C 1.1665(4) 0.8274(3) 0.4582(3) 0.0587(8) Uani 1 1 d . . .
C9 C 0.6431(3) 0.6246(2) 0.1727(2) 0.0476(7) Uani 1 1 d . . .
H9A H 0.6738 0.5601 0.1635 0.057 Uiso 1 1 calc R . .
H9B H 0.6005 0.6340 0.0971 0.057 Uiso 1 1 calc R . .
C10 C 0.5199(3) 0.5851(2) 0.2199(3) 0.0471(7) Uani 1 1 d . . .
C11 C 0.3669(4) 0.5196(3) 0.1439(3) 0.0638(9) Uani 1 1 d . . .
H11 H 0.3434 0.5028 0.0653 0.077 Uiso 1 1 calc R . .
C12 C 0.2508(4) 0.4795(3) 0.1828(3) 0.0741(10) Uani 1 1 d . . .
H12 H 0.1497 0.4351 0.1306 0.089 Uiso 1 1 calc R . .
C13 C 0.2827(4) 0.5045(3) 0.2984(3) 0.0592(8) Uani 1 1 d . . .
C14 C 0.4331(4) 0.5705(3) 0.3764(3) 0.0616(9) Uani 1 1 d . . .
H14 H 0.4555 0.5882 0.4548 0.074 Uiso 1 1 calc R . .
C15 C 0.5513(3) 0.6103(3) 0.3353(3) 0.0547(8) Uani 1 1 d . . .
H15 H 0.6527 0.6545 0.3872 0.066 Uiso 1 1 calc R . .
C16 C 0.1776(5) 0.4886(4) 0.4439(3) 0.0897(12) Uani 1 1 d . . .
H16A H 0.2514 0.4649 0.4872 0.134 Uiso 1 1 calc R . .
H16B H 0.0814 0.4446 0.4506 0.134 Uiso 1 1 calc R . .
H16C H 0.2137 0.5752 0.4729 0.134 Uiso 1 1 calc R . .
C17 C 0.6011(3) 0.9472(3) 0.2089(3) 0.0551(8) Uani 1 1 d . . .
H17A H 0.6336 1.0042 0.1653 0.066 Uiso 1 1 calc R . .
H17B H 0.6532 0.9918 0.2897 0.066 Uiso 1 1 calc R . .
C18 C 0.4303(3) 0.8960(3) 0.1753(2) 0.0491(7) Uani 1 1 d . . .
C19 C 0.3476(4) 0.8035(3) 0.2148(3) 0.0538(8) Uani 1 1 d . . .
H19 H 0.3989 0.7705 0.2640 0.065 Uiso 1 1 calc R . .
C20 C 0.1915(4) 0.7591(3) 0.1830(3) 0.0567(8) Uani 1 1 d . . .
H20 H 0.1385 0.6961 0.2097 0.068 Uiso 1 1 calc R . .
C21 C 0.1128(3) 0.8086(3) 0.1108(3) 0.0503(7) Uani 1 1 d . . .
C22 C 0.1931(4) 0.9016(3) 0.0720(3) 0.0559(8) Uani 1 1 d . . .
H22 H 0.1422 0.9360 0.0243 0.067 Uiso 1 1 calc R . .
C23 C 0.3492(4) 0.9439(3) 0.1038(3) 0.0561(8) Uani 1 1 d . . .
H23 H 0.4018 1.0065 0.0765 0.067 Uiso 1 1 calc R . .
C24 C -0.1252(4) 0.8083(4) 0.0099(3) 0.0740(10) Uani 1 1 d . . .
H24A H -0.0914 0.8918 0.0497 0.111 Uiso 1 1 calc R . .
H24B H -0.2330 0.7618 -0.0084 0.111 Uiso 1 1 calc R . .
H24C H -0.1066 0.8058 -0.0596 0.111 Uiso 1 1 calc R . .
C25 C 1.3634(4) 1.0685(4) 0.4217(5) 0.1067(16) Uani 1 1 d . . .
H25A H 1.4002 1.0259 0.4721 0.160 Uiso 1 1 calc R . .
H25B H 1.4469 1.1459 0.4322 0.160 Uiso 1 1 calc R . .
H25C H 1.3214 1.0200 0.3436 0.160 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 C6 1.372(3) . ?
N1 C5 1.408(3) . ?
N1 C9 1.477(3) . ?
N2 O4 1.216(3) . ?
N2 O3 1.233(3) . ?
N2 C7 1.452(4) . ?
N3 C6 1.340(3) . ?
N3 C17 1.459(3) . ?
N3 H3 0.8600 . ?
N4 C8 1.141(4) . ?
O1 S2 1.474(2) . ?
O2 C5 1.222(3) . ?
O5 C13 1.375(4) . ?
O5 C16 1.400(4) . ?
O6 C21 1.369(4) . ?
O6 C24 1.427(4) . ?
S1 C3 1.771(3) . ?
S1 C25 1.776(4) . ?
S2 C2 1.759(5) . ?
S2 C1 1.774(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.373(4) . ?
C3 C7 1.400(4) . ?
C4 C8 1.426(4) . ?
C4 C5 1.447(4) . ?
C6 C7 1.410(4) . ?
C9 C10 1.501(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.372(4) . ?
C10 C11 1.394(4) . ?
C11 C12 1.367(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C14 C15 1.405(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.506(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.385(4) . ?
C18 C23 1.388(4) . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(4) . ?
C22 C23 1.379(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C6 N1 C5 123.5(2) . . ?
C6 N1 C9 120.3(2) . . ?
C5 N1 C9 116.1(2) . . ?
O4 N2 O3 123.2(3) . . ?
O4 N2 C7 118.7(3) . . ?
O3 N2 C7 118.0(3) . . ?
C6 N3 C17 126.1(2) . . ?
C6 N3 H3 117.0 . . ?
C17 N3 H3 117.0 . . ?
C13 O5 C16 120.1(3) . . ?
C21 O6 C24 117.2(2) . . ?
C3 S1 C25 104.50(17) . . ?
O1 S2 C2 105.8(2) . . ?
O1 S2 C1 106.0(2) . . ?
C2 S2 C1 97.9(3) . . ?
S2 C1 H1A 109.5 . . ?
S2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S2 C2 H2A 109.5 . . ?
S2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
S2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C7 118.6(3) . . ?
C4 C3 S1 122.2(2) . . ?
C7 C3 S1 119.1(2) . . ?
C3 C4 C8 123.3(3) . . ?
C3 C4 C5 121.8(3) . . ?
C8 C4 C5 114.8(3) . . ?
O2 C5 N1 120.2(3) . . ?
O2 C5 C4 123.7(3) . . ?
N1 C5 C4 116.0(2) . . ?
N3 C6 N1 117.8(2) . . ?
N3 C6 C7 124.6(2) . . ?
N1 C6 C7 117.6(2) . . ?
C3 C7 C6 122.1(2) . . ?
C3 C7 N2 118.4(2) . . ?
C6 C7 N2 118.5(2) . . ?
N4 C8 C4 178.5(4) . . ?
N1 C9 C10 114.6(2) . . ?
N1 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C15 C10 C11 118.3(3) . . ?
C15 C10 C9 122.7(3) . . ?
C11 C10 C9 119.1(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 O5 115.8(3) . . ?
C12 C13 C14 120.0(3) . . ?
O5 C13 C14 124.2(3) . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 121.1(3) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 110.9(2) . . ?
N3 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C23 117.0(3) . . ?
C19 C18 C17 123.1(3) . . ?
C23 C18 C17 119.9(3) . . ?
C20 C19 C18 121.7(3) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
O6 C21 C22 124.7(3) . . ?
O6 C21 C20 116.2(3) . . ?
C22 C21 C20 119.1(3) . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C18 122.2(3) . . ?
C22 C23 H23 118.9 . . ?
C18 C23 H23 118.9 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
S1 C25 H25A 109.5 . . ?
S1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
S1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C25 S1 C3 C4 47.1(3) . . . . ?
C25 S1 C3 C7 -131.3(3) . . . . ?
C7 C3 C4 C8 -172.7(3) . . . . ?
S1 C3 C4 C8 8.9(4) . . . . ?
C7 C3 C4 C5 4.5(4) . . . . ?
S1 C3 C4 C5 -173.9(2) . . . . ?
C6 N1 C5 O2 175.8(3) . . . . ?
C9 N1 C5 O2 -1.9(4) . . . . ?
C6 N1 C5 C4 -2.1(4) . . . . ?
C9 N1 C5 C4 -179.8(2) . . . . ?
C3 C4 C5 O2 178.7(3) . . . . ?
C8 C4 C5 O2 -3.9(4) . . . . ?
C3 C4 C5 N1 -3.5(4) . . . . ?
C8 C4 C5 N1 173.9(3) . . . . ?
C17 N3 C6 N1 156.7(3) . . . . ?
C17 N3 C6 C7 -21.5(4) . . . . ?
C5 N1 C6 N3 -172.3(2) . . . . ?
C9 N1 C6 N3 5.4(4) . . . . ?
C5 N1 C6 C7 6.1(4) . . . . ?
C9 N1 C6 C7 -176.2(2) . . . . ?
C4 C3 C7 C6 -0.2(4) . . . . ?
S1 C3 C7 C6 178.3(2) . . . . ?
C4 C3 C7 N2 -168.5(3) . . . . ?
S1 C3 C7 N2 9.9(4) . . . . ?
N3 C6 C7 C3 173.3(3) . . . . ?
N1 C6 C7 C3 -5.0(4) . . . . ?
N3 C6 C7 N2 -18.4(4) . . . . ?
N1 C6 C7 N2 163.3(2) . . . . ?
O4 N2 C7 C3 -57.7(4) . . . . ?
O3 N2 C7 C3 120.5(3) . . . . ?
O4 N2 C7 C6 133.5(3) . . . . ?
O3 N2 C7 C6 -48.3(4) . . . . ?
C3 C4 C8 N4 123(15) . . . . ?
C5 C4 C8 N4 -54(16) . . . . ?
C6 N1 C9 C10 -75.9(3) . . . . ?
C5 N1 C9 C10 101.9(3) . . . . ?
N1 C9 C10 C15 -31.4(4) . . . . ?
N1 C9 C10 C11 149.0(3) . . . . ?
C15 C10 C11 C12 -1.0(5) . . . . ?
C9 C10 C11 C12 178.7(3) . . . . ?
C10 C11 C12 C13 0.7(6) . . . . ?
C11 C12 C13 O5 179.4(3) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C16 O5 C13 C12 -175.9(4) . . . . ?
C16 O5 C13 C14 3.5(6) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
O5 C13 C14 C15 -179.8(3) . . . . ?
C11 C10 C15 C14 0.5(5) . . . . ?
C9 C10 C15 C14 -179.2(3) . . . . ?
C13 C14 C15 C10 0.2(5) . . . . ?
C6 N3 C17 C18 -151.2(3) . . . . ?
N3 C17 C18 C19 52.8(4) . . . . ?
N3 C17 C18 C23 -128.8(3) . . . . ?
C23 C18 C19 C20 1.2(5) . . . . ?
C17 C18 C19 C20 179.6(3) . . . . ?
C18 C19 C20 C21 -1.0(5) . . . . ?
C24 O6 C21 C22 -3.7(4) . . . . ?
C24 O6 C21 C20 178.3(3) . . . . ?
C19 C20 C21 O6 178.3(3) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
O6 C21 C22 C23 -177.4(3) . . . . ?
C20 C21 C22 C23 0.6(5) . . . . ?
C21 C22 C23 C18 -0.4(5) . . . . ?
C19 C18 C23 C22 -0.5(5) . . . . ?
C17 C18 C23 C22 -179.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1553238'
_audit_update_record             
;
2017-05-31 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 N4 O3 S'
_chemical_formula_weight         282.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.033(4)
_cell_length_b                   14.483(12)
_cell_length_c                   19.140(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.932(10)
_cell_angle_gamma                90
_cell_volume                     1385(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6990
_cell_measurement_theta_min      0.844656
_cell_measurement_theta_max      28.2795

_exptl_crystal_description       block
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12559
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.768
_diffrn_reflns_theta_max         27.885
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3203
_reflns_number_gt                2082
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.1113P)²+0.8311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3203
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.2280
_refine_ls_wR_factor_gt          0.2032
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.003
_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
N1 N 0.5643(6) 0.34840(19) 0.17101(16) 0.0622(7) Uani 1 1 d . . . . .
N2 N 0.3196(5) 0.12212(17) 0.22673(13) 0.0493(6) Uani 1 1 d . . . . .
N3 N 0.6038(5) 0.17191(16) 0.14373(13) 0.0496(6) Uani 1 1 d . . . . .
N4 N 0.5845(9) -0.1586(2) 0.1184(2) 0.0931(11) Uani 1 1 d . . . . .
O1 O 0.7914(6) 0.3676(2) 0.19359(19) 0.0958(10) Uani 1 1 d . . . . .
O2 O 0.4460(8) 0.3740(2) 0.11574(17) 0.1033(11) Uani 1 1 d . . . . .
O3 O 0.1946(5) -0.02986(17) 0.23139(13) 0.0679(7) Uani 1 1 d . . . . .
S1 S 0.84165(19) 0.06059(7) 0.05889(5) 0.0672(3) Uani 1 1 d . . . . .
C1 C 0.4155(7) 0.2868(2) 0.21498(19) 0.0629(9) Uani 1 1 d . . . . .
H1A H 0.2270 0.3028 0.2088 0.075 Uiso 1 1 calc R U . . .
H1B H 0.4830 0.2946 0.2643 0.075 Uiso 1 1 calc R U . . .
C2 C 0.4508(6) 0.1876(2) 0.19331(16) 0.0476(7) Uani 1 1 d . . . . .
C3 C 0.3304(6) 0.0277(2) 0.20628(16) 0.0504(7) Uani 1 1 d . . . . .
C4 C 0.5113(6) 0.0108(2) 0.15441(15) 0.0497(7) Uani 1 1 d . . . . .
C5 C 0.5490(7) -0.0833(2) 0.13422(18) 0.0623(8) Uani 1 1 d . . . . .
C6 C 0.6368(6) 0.0827(2) 0.12410(15) 0.0478(7) Uani 1 1 d . . . . .
C7 C 0.9251(9) 0.1742(3) 0.0303(2) 0.0787(11) Uani 1 1 d . . . . .
H7A H 0.7642 0.2063 0.0125 0.118 Uiso 1 1 calc R U . . .
H7B H 1.0395 0.1690 -0.0062 0.118 Uiso 1 1 calc R U . . .
H7C H 1.0162 0.2077 0.0693 0.118 Uiso 1 1 calc R U . . .
C8 C 0.1599(7) 0.1433(3) 0.28530(18) 0.0644(9) Uani 1 1 d . . . . .
H8A H 0.0259 0.0955 0.2874 0.077 Uiso 1 1 calc R U . . .
H8B H 0.0671 0.2014 0.2756 0.077 Uiso 1 1 calc R U . . .
C9 C 0.3307(13) 0.1496(6) 0.3566(3) 0.141(3) Uani 1 1 d . . . . .
H9A H 0.4289 0.2072 0.3563 0.170 Uiso 1 1 calc R U . . .
H9B H 0.2066 0.1568 0.3913 0.170 Uiso 1 1 calc R U . . .
C10 C 0.5010(13) 0.0884(7) 0.3814(3) 0.159(3) Uani 1 1 d . . . . .
H10A H 0.6307 0.0823 0.3481 0.190 Uiso 1 1 calc R U . . .
H10B H 0.4059 0.0301 0.3811 0.190 Uiso 1 1 calc R U . . .
C11 C 0.6589(11) 0.0988(5) 0.4544(2) 0.1116(18) Uani 1 1 d . . . . .
H11A H 0.7758 0.1512 0.4546 0.167 Uiso 1 1 calc R U . . .
H11B H 0.7631 0.0441 0.4656 0.167 Uiso 1 1 calc R U . . .
H11C H 0.5370 0.1077 0.4887 0.167 Uiso 1 1 calc R U . . .


_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 O1 1.205(4) . ?
N1 O2 1.208(4) . ?
N1 C1 1.489(4) . ?
N2 C2 1.359(4) . ?
N2 C3 1.425(4) . ?
N2 C8 1.488(4) . ?
N3 C2 1.312(4) . ?
N3 C6 1.362(4) . ?
N4 C5 1.152(5) . ?
O3 C3 1.214(4) . ?
S1 C6 1.742(3) . ?
S1 C7 1.799(4) . ?
C1 C2 1.512(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C4 1.446(4) . ?
C4 C6 1.381(4) . ?
C4 C5 1.436(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.525(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.283(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.529(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
O1 N1 O2 126.1(4) . . ?
O1 N1 C1 117.1(3) . . ?
O2 N1 C1 116.8(3) . . ?
C2 N2 C3 120.2(2) . . ?
C2 N2 C8 123.3(3) . . ?
C3 N2 C8 116.5(3) . . ?
C2 N3 C6 117.8(3) . . ?
C6 S1 C7 103.33(17) . . ?
N1 C1 C2 109.3(3) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
N3 C2 N2 125.5(3) . . ?
N3 C2 C1 117.5(3) . . ?
N2 C2 C1 117.0(3) . . ?
O3 C3 N2 120.6(3) . . ?
O3 C3 C4 125.9(3) . . ?
N2 C3 C4 113.5(3) . . ?
C6 C4 C5 121.3(3) . . ?
C6 C4 C3 121.2(3) . . ?
C5 C4 C3 117.4(3) . . ?
N4 C5 C4 178.7(4) . . ?
N3 C6 C4 121.5(3) . . ?
N3 C6 S1 118.3(2) . . ?
C4 C6 S1 120.2(2) . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 112.9(3) . . ?
N2 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 124.6(7) . . ?
C10 C9 H9A 106.2 . . ?
C8 C9 H9A 106.2 . . ?
C10 C9 H9B 106.2 . . ?
C8 C9 H9B 106.2 . . ?
H9A C9 H9B 106.4 . . ?
C9 C10 C11 121.3(7) . . ?
C9 C10 H10A 107.0 . . ?
C11 C10 H10A 107.0 . . ?
C9 C10 H10B 107.0 . . ?
C11 C10 H10B 107.0 . . ?
H10A C10 H10B 106.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O1 N1 C1 C2 -92.0(4) . . . . ?
O2 N1 C1 C2 87.6(4) . . . . ?
C6 N3 C2 N2 -0.5(4) . . . . ?
C6 N3 C2 C1 179.9(3) . . . . ?
C3 N2 C2 N3 -3.3(4) . . . . ?
C8 N2 C2 N3 176.7(3) . . . . ?
C3 N2 C2 C1 176.3(3) . . . . ?
C8 N2 C2 C1 -3.7(4) . . . . ?
N1 C1 C2 N3 1.9(4) . . . . ?
N1 C1 C2 N2 -177.8(3) . . . . ?
C2 N2 C3 O3 -173.3(3) . . . . ?
C8 N2 C3 O3 6.7(4) . . . . ?
C2 N2 C3 C4 6.2(4) . . . . ?
C8 N2 C3 C4 -173.8(3) . . . . ?
O3 C3 C4 C6 173.5(3) . . . . ?
N2 C3 C4 C6 -5.9(4) . . . . ?
O3 C3 C4 C5 -4.7(5) . . . . ?
N2 C3 C4 C5 175.8(3) . . . . ?
C2 N3 C6 C4 0.9(4) . . . . ?
C2 N3 C6 S1 -179.4(2) . . . . ?
C5 C4 C6 N3 -179.2(3) . . . . ?
C3 C4 C6 N3 2.6(4) . . . . ?
C5 C4 C6 S1 1.1(4) . . . . ?
C3 C4 C6 S1 -177.1(2) . . . . ?
C7 S1 C6 N3 -5.8(3) . . . . ?
C7 S1 C6 C4 173.9(3) . . . . ?
C2 N2 C8 C9 -83.5(5) . . . . ?
C3 N2 C8 C9 96.5(5) . . . . ?
N2 C8 C9 C10 -50.5(9) . . . . ?
C8 C9 C10 C11 -178.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A O1 0.97 2.37 3.330(5) 170.5 1_455
C1 H1A O1 0.97 2.37 3.330(5) 170.5 1_455
C1 H1A O1 0.97 2.37 3.330(5) 170.5 1_455
C1 H1A O1 0.97 2.37 3.330(5) 170.5 1_455

_refine_diff_density_max         0.657
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3

