# 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_fx141125a
_database_code_depnum_ccdc_archive 'CCDC 1416185'
_audit_update_record             
;
2016-03-02 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2016-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H14 N4 O2 S, C7 H5 N O3 S'
_chemical_formula_sum            'C19 H19 N5 O5 S2'
_chemical_formula_weight         461.51
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0729(3)
_cell_length_b                   17.6015(7)
_cell_length_c                   14.4311(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.488(4)
_cell_angle_gamma                90.00
_cell_volume                     1985.40(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2642
_cell_measurement_temperature    220.00(10)
_cell_measurement_theta_max      73.3000
_cell_measurement_theta_min      4.0400
_exptl_absorpt_coefficient_mu    2.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7165
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         4.04
_diffrn_ambient_temperature      220.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -41.00   36.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000  -90.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega  -96.00  -40.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  125.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   36.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega   18.00   57.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2343 -125.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  5 omega   41.00   67.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2343 -125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   86.00  158.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   77.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
  7 omega   29.00   89.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
  8 omega   29.00   96.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -77.0000   60.0000 67

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00   70.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
 10 omega  113.00  139.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   91.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   72.00  173.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   15.0000  120.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1863259000
_diffrn_orient_matrix_UB_12      -0.0121360000
_diffrn_orient_matrix_UB_13      0.0053141000
_diffrn_orient_matrix_UB_21      -0.0544507000
_diffrn_orient_matrix_UB_22      0.0716370000
_diffrn_orient_matrix_UB_23      -0.0613866000
_diffrn_orient_matrix_UB_31      -0.0338014000
_diffrn_orient_matrix_UB_32      -0.0488013000
_diffrn_orient_matrix_UB_33      -0.0914854000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2853
_reflns_number_total             3553
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.6213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1302
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C2(H2), C3(H3), C4(H4), C5(H5A)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S2 S 0.50176(9) 0.56061(4) 0.79808(5) 0.0321(2) Uani 1 d . . .
O4 O 0.4184(3) 0.63335(14) 0.77609(18) 0.0501(6) Uani 1 d . . .
O5 O 0.4375(3) 0.51285(14) 0.86257(16) 0.0432(6) Uani 1 d . . .
N2 N 1.2385(4) 0.60504(17) 0.9882(2) 0.0386(6) Uani 1 d . . .
H2A H 1.272(5) 0.590(2) 1.051(3) 0.046 Uiso 1 d . . R
H2B H 1.312(5) 0.589(2) 0.956(3) 0.046 Uiso 1 d . . R
N3 N 0.4781(3) 0.52231(13) 0.69399(16) 0.0293(5) Uani 1 d . . .
N4 N 0.6393(3) 0.40982(13) 0.74675(16) 0.0259(5) Uani 1 d . . .
N5 N 0.4634(3) 0.42392(13) 0.59078(16) 0.0256(5) Uani 1 d . . .
H5 H 0.384(4) 0.447(2) 0.553(2) 0.031 Uiso 1 d . . R
C8 C 1.0662(4) 0.59648(16) 0.9435(2) 0.0307(6) Uani 1 d . . .
C9 C 0.9437(4) 0.58877(19) 0.9960(2) 0.0380(7) Uani 1 d . . .
H9 H 0.9773 0.5907 1.0625 0.046 Uiso 1 calc . . R
C10 C 0.7731(4) 0.57836(19) 0.9506(2) 0.0367(7) Uani 1 d . . .
H10 H 0.6928 0.5734 0.9864 0.044 Uiso 1 calc . . R
C11 C 0.7216(4) 0.57531(15) 0.8510(2) 0.0284(6) Uani 1 d . . .
C12 C 0.8394(4) 0.58507(17) 0.7976(2) 0.0322(6) Uani 1 d . . .
H12 H 0.8041 0.5842 0.7311 0.039 Uiso 1 calc . . R
C13 C 1.0111(4) 0.59628(16) 0.8427(2) 0.0323(6) Uani 1 d . . .
H13 H 1.0899 0.6037 0.8063 0.039 Uiso 1 calc . . R
C14 C 0.5302(3) 0.45152(15) 0.68129(18) 0.0241(5) Uani 1 d . . .
C15 C 0.6820(4) 0.34125(15) 0.7200(2) 0.0274(6) Uani 1 d . . .
C16 C 0.6192(4) 0.31222(16) 0.6275(2) 0.0287(6) Uani 1 d . . .
H16 H 0.6547 0.2650 0.6109 0.034 Uiso 1 calc . . R
C17 C 0.5049(3) 0.35474(16) 0.56240(19) 0.0265(6) Uani 1 d . . .
C18 C 0.7989(4) 0.29388(17) 0.7933(2) 0.0362(7) Uani 1 d . . .
H18A H 0.8960 0.3236 0.8254 0.054 Uiso 1 calc . . GR
H18B H 0.8368 0.2511 0.7629 0.054 Uiso 1 calc . . GR
H18C H 0.7394 0.2763 0.8391 0.054 Uiso 1 calc . . GR
C19 C 0.4203(4) 0.33069(18) 0.4630(2) 0.0350(7) Uani 1 d . . .
H19A H 0.2996 0.3253 0.4565 0.053 Uiso 1 calc . . GR
H19B H 0.4670 0.2829 0.4497 0.053 Uiso 1 calc . . GR
H19C H 0.4398 0.3683 0.4188 0.053 Uiso 1 calc . . GR
S1 S 1.10322(9) 0.68287(4) 0.56077(5) 0.02928(19) Uani 1 d . . .
O1 O 1.2230(3) 0.74314(12) 0.56637(16) 0.0394(5) Uani 1 d . . .
O2 O 1.0049(3) 0.68126(14) 0.63046(14) 0.0398(5) Uani 1 d . . .
O3 O 1.2013(3) 0.49750(12) 0.46003(15) 0.0356(5) Uani 1 d . . .
N1 N 1.1994(3) 0.59910(14) 0.55834(17) 0.0315(5) Uani 1 d . . .
H1 H 1.284(5) 0.579(2) 0.602(3) 0.038 Uiso 1 d . . R
C1 C 0.9744(4) 0.67130(15) 0.44345(19) 0.0264(6) Uani 1 d . . .
C2 C 0.8575(4) 0.72230(16) 0.3918(2) 0.0308(6) Uani 1 d . . .
H2 H 0.8374 0.7690 0.4172 0.037 Uiso 1 calc . . R
C3 C 0.7705(4) 0.70038(18) 0.2993(2) 0.0358(7) Uani 1 d . . .
H3 H 0.6907 0.7331 0.2619 0.043 Uiso 1 calc . . R
C4 C 0.8016(4) 0.63057(19) 0.2627(2) 0.0365(7) Uani 1 d . . .
H4 H 0.7412 0.6171 0.2012 0.044 Uiso 1 calc . . R
C5 C 0.9205(4) 0.58034(17) 0.3155(2) 0.0319(6) Uani 1 d . . .
H5A H 0.9410 0.5336 0.2903 0.038 Uiso 1 calc . . R
C6 C 1.0083(4) 0.60192(16) 0.40734(19) 0.0265(6) Uani 1 d . . .
C7 C 1.1438(4) 0.55955(16) 0.4753(2) 0.0290(6) Uani 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
S2 O4 1.444(2) . ?
S2 O5 1.443(3) . ?
S2 N3 1.614(2) . ?
S2 C11 1.767(3) . ?
N2 C8 1.387(4) . ?
N3 C14 1.342(4) . ?
N4 C14 1.338(3) . ?
N4 C15 1.338(4) . ?
N5 C14 1.371(3) . ?
N5 C17 1.353(4) . ?
C8 C9 1.395(4) . ?
C8 C13 1.410(4) . ?
C9 C10 1.381(5) . ?
C10 C11 1.393(4) . ?
C11 C12 1.377(4) . ?
C12 C13 1.390(4) . ?
C15 C16 1.400(4) . ?
C15 C18 1.485(4) . ?
C16 C17 1.364(4) . ?
C17 C19 1.487(4) . ?
S1 O1 1.424(2) . ?
S1 O2 1.429(2) . ?
S1 N1 1.671(3) . ?
S1 C1 1.763(3) . ?
O3 C7 1.229(4) . ?
N1 C7 1.361(4) . ?
C1 C2 1.379(4) . ?
C1 C6 1.382(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.385(5) . ?
C4 C5 1.385(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.476(4) . ?

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
O4 S2 N3 103.04(14) . . ?
O4 S2 C11 109.13(14) . . ?
O5 S2 O4 115.80(16) . . ?
O5 S2 N3 112.27(13) . . ?
O5 S2 C11 106.89(14) . . ?
N3 S2 C11 109.62(13) . . ?
C14 N3 S2 123.1(2) . . ?
C15 N4 C14 117.6(2) . . ?
C17 N5 C14 122.6(2) . . ?
N2 C8 C9 121.5(3) . . ?
N2 C8 C13 120.1(3) . . ?
C9 C8 C13 118.4(3) . . ?
C10 C9 C8 120.9(3) . . ?
C9 C10 C11 120.0(3) . . ?
C10 C11 S2 117.4(2) . . ?
C12 C11 S2 122.4(2) . . ?
C12 C11 C10 120.1(3) . . ?
C11 C12 C13 120.2(3) . . ?
C12 C13 C8 120.3(3) . . ?
N3 C14 N5 113.4(2) . . ?
N4 C14 N3 125.9(2) . . ?
N4 C14 N5 120.7(2) . . ?
N4 C15 C16 123.1(3) . . ?
N4 C15 C18 117.7(3) . . ?
C16 C15 C18 119.2(3) . . ?
C17 C16 C15 118.5(3) . . ?
N5 C17 C16 117.5(2) . . ?
N5 C17 C19 117.3(3) . . ?
C16 C17 C19 125.2(3) . . ?
O1 S1 O2 117.64(14) . . ?
O1 S1 N1 110.25(13) . . ?
O1 S1 C1 111.69(13) . . ?
O2 S1 N1 109.88(14) . . ?
O2 S1 C1 112.05(13) . . ?
N1 S1 C1 92.49(13) . . ?
C7 N1 S1 114.7(2) . . ?
C2 C1 S1 127.2(2) . . ?
C2 C1 C6 123.0(3) . . ?
C6 C1 S1 109.8(2) . . ?
C1 C2 C3 116.7(3) . . ?
C4 C3 C2 120.9(3) . . ?
C3 C4 C5 121.5(3) . . ?
C4 C5 C6 117.9(3) . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 C7 112.3(2) . . ?
C5 C6 C7 127.7(3) . . ?
O3 C7 N1 123.9(3) . . ?
O3 C7 C6 125.5(3) . . ?
N1 C7 C6 110.7(2) . . ?

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
N2 H2B O5 0.88(4) 2.31(4) 3.156(4) 160(4) 1_655
N5 H5 O3 0.83(4) 1.95(4) 2.778(3) 177(3) 1_455
C10 H10 O5 0.93 2.59 2.926(4) 101.5 .
C12 H12 N3 0.93 2.77 3.128(4) 103.8 .
N1 H1 N3 0.89(4) 2.04(4) 2.919(3) 174(3) 1_655

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
S2 N3 C14 N4 -16.0(4) . . . . ?
S2 N3 C14 N5 165.6(2) . . . . ?
S2 C11 C12 C13 -179.8(2) . . . . ?
O4 S2 N3 C14 -176.6(2) . . . . ?
O4 S2 C11 C10 93.0(3) . . . . ?
O4 S2 C11 C12 -85.7(3) . . . . ?
O5 S2 N3 C14 -51.3(3) . . . . ?
O5 S2 C11 C10 -32.9(3) . . . . ?
O5 S2 C11 C12 148.4(2) . . . . ?
N2 C8 C9 C10 -178.3(3) . . . . ?
N2 C8 C13 C12 177.8(3) . . . . ?
N3 S2 C11 C10 -154.8(2) . . . . ?
N3 S2 C11 C12 26.5(3) . . . . ?
N4 C15 C16 C17 -2.2(4) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C9 C8 C13 C12 -2.9(4) . . . . ?
C9 C10 C11 S2 179.2(3) . . . . ?
C9 C10 C11 C12 -2.1(5) . . . . ?
C10 C11 C12 C13 1.5(4) . . . . ?
C11 S2 N3 C14 67.4(3) . . . . ?
C11 C12 C13 C8 1.1(4) . . . . ?
C13 C8 C9 C10 2.4(5) . . . . ?
C14 N4 C15 C16 0.6(4) . . . . ?
C14 N4 C15 C18 -178.2(3) . . . . ?
C14 N5 C17 C16 -0.6(4) . . . . ?
C14 N5 C17 C19 178.5(3) . . . . ?
C15 N4 C14 N3 -177.4(3) . . . . ?
C15 N4 C14 N5 0.9(4) . . . . ?
C15 C16 C17 N5 2.1(4) . . . . ?
C15 C16 C17 C19 -177.0(3) . . . . ?
C17 N5 C14 N3 177.5(2) . . . . ?
C17 N5 C14 N4 -1.0(4) . . . . ?
C18 C15 C16 C17 176.6(3) . . . . ?
S1 N1 C7 O3 178.9(2) . . . . ?
S1 N1 C7 C6 -0.4(3) . . . . ?
S1 C1 C2 C3 179.7(2) . . . . ?
S1 C1 C6 C5 179.7(2) . . . . ?
S1 C1 C6 C7 -1.7(3) . . . . ?
O1 S1 N1 C7 -114.7(2) . . . . ?
O1 S1 C1 C2 -64.9(3) . . . . ?
O1 S1 C1 C6 114.2(2) . . . . ?
O2 S1 N1 C7 114.1(2) . . . . ?
O2 S1 C1 C2 69.5(3) . . . . ?
O2 S1 C1 C6 -111.4(2) . . . . ?
N1 S1 C1 C2 -177.9(3) . . . . ?
N1 S1 C1 C6 1.2(2) . . . . ?
C1 S1 N1 C7 -0.5(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 C6 C7 O3 -177.9(3) . . . . ?
C1 C6 C7 N1 1.4(3) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C2 C1 C6 C7 177.5(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C6 C7 -177.8(3) . . . . ?
C5 C6 C7 O3 0.6(5) . . . . ?
C5 C6 C7 N1 179.9(3) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_g150513a
_database_code_depnum_ccdc_archive 'CCDC 1437001'
_audit_update_record             
;
2016-03-02 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2016-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H15 N4 O2 S, C7 H4 N O3 S'
_chemical_formula_sum            'C19 H19 N5 O5 S2'
_chemical_formula_weight         461.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   10.5425(3)
_cell_length_b                   16.0431(4)
_cell_length_c                   25.3246(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4283.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7010
_cell_measurement_temperature    220.00(10)
_cell_measurement_theta_max      28.4440
_cell_measurement_theta_min      3.3290
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21676
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.82
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   39.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00  -35.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -57.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00    4.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega -104.00  -57.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327 -178.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega  -23.00   19.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -99.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
  6 omega  -44.00    9.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327   57.0000  -60.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0564260000
_diffrn_orient_matrix_UB_12      0.0014123000
_diffrn_orient_matrix_UB_13      -0.0152245000
_diffrn_orient_matrix_UB_21      -0.0319271000
_diffrn_orient_matrix_UB_22      -0.0199044000
_diffrn_orient_matrix_UB_23      -0.0211988000
_diffrn_orient_matrix_UB_31      -0.0180781000
_diffrn_orient_matrix_UB_32      0.0394337000
_diffrn_orient_matrix_UB_33      -0.0101642000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3426
_reflns_number_total             4376
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1428
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All H(H,H) groups
2. Restrained distances
 N4-H4A = N4-H4B
 0.8 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C5(H5), C4(H4), C9(H9), C15(H15), C16(H16), C18(H18),
 C17(H17)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S2 S 0.42405(6) 0.19692(3) 0.335195(19) 0.04129(19) Uani 1 d . . .
O1 O 0.49244(19) 0.15659(10) 0.29376(6) 0.0570(5) Uani 1 d . . .
O2 O 0.29945(17) 0.16738(11) 0.34866(7) 0.0565(5) Uani 1 d . . .
N1 N 0.50115(18) 0.18410(11) 0.39162(7) 0.0376(4) Uani 1 d . . .
H1 H 0.461(2) 0.1657(15) 0.4176(9) 0.045 Uiso 1 d . . R
N2 N 0.67422(16) 0.17529(10) 0.44682(6) 0.0288(4) Uani 1 d . . .
H2 H 0.625(2) 0.1522(13) 0.4708(8) 0.035 Uiso 1 d . . R
N4 N 0.3856(3) 0.55573(13) 0.29058(9) 0.0638(7) Uani 1 d . . D
H4A H 0.430(3) 0.5769(18) 0.2668(9) 0.077 Uiso 1 d . . DR
H4B H 0.333(3) 0.5811(17) 0.3078(11) 0.077 Uiso 1 d . . DR
N3 N 0.69819(18) 0.23058(10) 0.36143(6) 0.0365(4) Uani 1 d . . .
C6 C 0.4161(2) 0.30316(12) 0.32205(7) 0.0366(5) Uani 1 d . . .
C3 C 0.3951(2) 0.47250(13) 0.30036(8) 0.0419(5) Uani 1 d . . .
C11 C 0.9012(3) 0.27532(18) 0.32774(9) 0.0589(7) Uani 1 d . . .
H11A H 0.9156 0.2325 0.3019 0.108(12) Uiso 1 calc . . GR
H11B H 0.9811 0.2941 0.3415 0.161 Uiso 1 calc . . GR
H11C H 0.8578 0.3213 0.3115 0.161 Uiso 1 calc . . GR
C1 C 0.5033(2) 0.34142(13) 0.28857(7) 0.0369(5) Uani 1 d . . .
H1A H 0.5694 0.3107 0.2740 0.037(6) Uiso 1 calc . . R
C7 C 0.6275(2) 0.19762(11) 0.39924(7) 0.0317(4) Uani 1 d . . .
C12 C 0.8393(2) 0.16474(13) 0.51282(7) 0.0371(5) Uani 1 d . . .
H12A H 0.8030 0.2029 0.5378 0.080(9) Uiso 1 calc . . GR
H12B H 0.9301 0.1675 0.5148 0.120 Uiso 1 calc . . GR
H12C H 0.8118 0.1091 0.5208 0.120 Uiso 1 calc . . GR
C2 C 0.4913(2) 0.42485(13) 0.27718(7) 0.0397(5) Uani 1 d . . .
H2A H 0.5477 0.4499 0.2538 0.045(6) Uiso 1 calc . . R
C10 C 0.79734(19) 0.18748(11) 0.45877(8) 0.0303(4) Uani 1 d . . .
C5 C 0.3185(2) 0.34982(14) 0.34482(8) 0.0426(5) Uani 1 d . . .
H5 H 0.2601 0.3242 0.3670 0.069(8) Uiso 1 calc . . R
C4 C 0.3089(2) 0.43347(15) 0.33440(8) 0.0465(6) Uani 1 d . . .
H4 H 0.2446 0.4645 0.3501 0.052(7) Uiso 1 calc . . R
C9 C 0.8747(2) 0.22112(12) 0.42051(7) 0.0367(5) Uani 1 d . . .
H9 H 0.9604 0.2303 0.4270 0.031(5) Uiso 1 calc . . R
C8 C 0.8217(2) 0.24095(12) 0.37194(8) 0.0390(5) Uani 1 d . . .
S1 S 0.21573(5) 0.09696(3) 0.482111(19) 0.03392(17) Uani 1 d . . .
O3 O 0.17321(16) 0.03650(9) 0.44449(6) 0.0468(4) Uani 1 d . . .
O5 O 0.54900(14) 0.10228(9) 0.52362(5) 0.0397(4) Uani 1 d . . .
O4 O 0.14610(15) 0.17379(9) 0.48392(6) 0.0452(4) Uani 1 d . . .
N5 N 0.36653(17) 0.11625(10) 0.47575(6) 0.0332(4) Uani 1 d . . .
C14 C 0.35279(19) 0.05360(11) 0.56049(7) 0.0315(4) Uani 1 d . . .
C15 C 0.3912(2) 0.02153(13) 0.60851(8) 0.0405(5) Uani 1 d . . .
H15 H 0.4760 0.0223 0.6185 0.056(7) Uiso 1 calc . . R
C19 C 0.2261(2) 0.05201(12) 0.54589(8) 0.0338(5) Uani 1 d . . .
C16 C 0.2981(3) -0.01201(14) 0.64145(9) 0.0471(6) Uani 1 d . . .
H16 H 0.3210 -0.0333 0.6743 0.050(7) Uiso 1 calc . . R
C13 C 0.4326(2) 0.09243(12) 0.51847(7) 0.0322(4) Uani 1 d . . .
C18 C 0.1327(2) 0.01845(13) 0.57774(8) 0.0419(5) Uani 1 d . . .
H18 H 0.0480 0.0176 0.5675 0.035(6) Uiso 1 calc . . R
C17 C 0.1721(3) -0.01398(13) 0.62593(9) 0.0467(6) Uani 1 d . . .
H17 H 0.1123 -0.0377 0.6484 0.063(8) Uiso 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
S2 O1 1.4283(17) . ?
S2 O2 1.4375(19) . ?
S2 N1 1.6568(17) . ?
S2 C6 1.739(2) . ?
N1 H1 0.84(2) . ?
N1 C7 1.363(3) . ?
N2 H2 0.88(2) . ?
N2 C7 1.350(2) . ?
N2 C10 1.347(3) . ?
N4 H4A 0.834(17) . ?
N4 H4B 0.816(17) . ?
N4 C3 1.362(3) . ?
N3 C7 1.324(2) . ?
N3 C8 1.339(3) . ?
C6 C1 1.393(3) . ?
C6 C5 1.397(3) . ?
C3 C2 1.399(3) . ?
C3 C4 1.400(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 C8 1.504(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.375(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C10 1.484(3) . ?
C2 H2A 0.9300 . ?
C10 C9 1.377(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.388(3) . ?
S1 O3 1.4317(15) . ?
S1 O4 1.4354(15) . ?
S1 N5 1.6276(18) . ?
S1 C19 1.772(2) . ?
O5 C13 1.244(3) . ?
N5 C13 1.342(3) . ?
C14 C15 1.381(3) . ?
C14 C19 1.386(3) . ?
C14 C13 1.493(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.396(3) . ?
C19 C18 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.390(3) . ?
C17 H17 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
O1 S2 O2 119.09(11) . . ?
O1 S2 N1 109.26(10) . . ?
O1 S2 C6 109.13(10) . . ?
O2 S2 N1 101.70(10) . . ?
O2 S2 C6 108.94(11) . . ?
N1 S2 C6 108.09(9) . . ?
S2 N1 H1 118.3(17) . . ?
C7 N1 S2 125.56(14) . . ?
C7 N1 H1 116.1(17) . . ?
C7 N2 H2 121.0(14) . . ?
C10 N2 H2 118.1(14) . . ?
C10 N2 C7 120.90(18) . . ?
H4A N4 H4B 124(3) . . ?
C3 N4 H4A 119(2) . . ?
C3 N4 H4B 116(2) . . ?
C7 N3 C8 116.95(17) . . ?
C1 C6 S2 121.11(17) . . ?
C1 C6 C5 120.07(19) . . ?
C5 C6 S2 118.80(17) . . ?
N4 C3 C2 120.9(2) . . ?
N4 C3 C4 120.2(2) . . ?
C2 C3 C4 119.0(2) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
C6 C1 H1A 120.1 . . ?
C2 C1 C6 119.7(2) . . ?
C2 C1 H1A 120.1 . . ?
N2 C7 N1 116.14(17) . . ?
N3 C7 N1 120.76(17) . . ?
N3 C7 N2 123.10(19) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2A 119.6 . . ?
N2 C10 C12 117.30(17) . . ?
N2 C10 C9 118.03(18) . . ?
C9 C10 C12 124.67(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C10 C9 H9 120.8 . . ?
C10 C9 C8 118.3(2) . . ?
C8 C9 H9 120.8 . . ?
N3 C8 C11 116.1(2) . . ?
N3 C8 C9 122.65(18) . . ?
C9 C8 C11 121.3(2) . . ?
O3 S1 O4 116.29(10) . . ?
O3 S1 N5 111.64(9) . . ?
O3 S1 C19 110.49(9) . . ?
O4 S1 N5 109.85(9) . . ?
O4 S1 C19 110.61(9) . . ?
N5 S1 C19 96.16(9) . . ?
C13 N5 S1 111.89(13) . . ?
C15 C14 C19 120.68(19) . . ?
C15 C14 C13 128.2(2) . . ?
C19 C14 C13 111.13(17) . . ?
C14 C15 H15 121.2 . . ?
C14 C15 C16 117.6(2) . . ?
C16 C15 H15 121.2 . . ?
C14 C19 S1 107.16(14) . . ?
C18 C19 S1 130.28(18) . . ?
C18 C19 C14 122.55(19) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.6 . . ?
O5 C13 N5 124.05(17) . . ?
O5 C13 C14 122.28(17) . . ?
N5 C13 C14 113.66(18) . . ?
C19 C18 H18 121.8 . . ?
C19 C18 C17 116.5(2) . . ?
C17 C18 H18 121.8 . . ?
C16 C17 C18 121.8(2) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?

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
N1 H1 N5 0.84(2) 1.95(2) 2.782(2) 176(2) .
N2 H2 O5 0.88(2) 1.75(2) 2.626(2) 171(2) .
N4 H4A O1 0.834(17) 2.158(19) 2.972(3) 165(3) 4_655
N4 H4B O2 0.816(17) 2.220(18) 3.029(3) 171(3) 7_665
C1 H1A O1 0.93 2.65 2.970(3) 101.0 .
C5 H5 O2 0.93 2.59 2.935(3) 102.4 .
C15 H15 O5 0.93 2.83 3.011(3) 92.0 .

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
S2 N1 C7 N2 -173.41(13) . . . . ?
S2 N1 C7 N3 6.4(3) . . . . ?
S2 C6 C1 C2 177.24(15) . . . . ?
S2 C6 C5 C4 -178.93(17) . . . . ?
O1 S2 N1 C7 48.5(2) . . . . ?
O1 S2 C6 C1 -22.0(2) . . . . ?
O1 S2 C6 C5 156.64(17) . . . . ?
O2 S2 N1 C7 175.23(17) . . . . ?
O2 S2 C6 C1 -153.53(16) . . . . ?
O2 S2 C6 C5 25.10(19) . . . . ?
N1 S2 C6 C1 96.74(17) . . . . ?
N1 S2 C6 C5 -84.63(18) . . . . ?
N2 C10 C9 C8 0.3(3) . . . . ?
N4 C3 C2 C1 177.7(2) . . . . ?
N4 C3 C4 C5 -179.4(2) . . . . ?
C6 S2 N1 C7 -70.17(19) . . . . ?
C6 C1 C2 C3 2.3(3) . . . . ?
C6 C5 C4 C3 1.0(3) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C7 N2 C10 C12 177.22(17) . . . . ?
C7 N2 C10 C9 -1.8(3) . . . . ?
C7 N3 C8 C11 177.66(19) . . . . ?
C7 N3 C8 C9 -2.1(3) . . . . ?
C12 C10 C9 C8 -178.68(18) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C10 N2 C7 N1 -178.70(16) . . . . ?
C10 N2 C7 N3 1.5(3) . . . . ?
C10 C9 C8 N3 1.7(3) . . . . ?
C10 C9 C8 C11 -178.0(2) . . . . ?
C5 C6 C1 C2 -1.4(3) . . . . ?
C4 C3 C2 C1 -1.6(3) . . . . ?
C8 N3 C7 N1 -179.31(18) . . . . ?
C8 N3 C7 N2 0.5(3) . . . . ?
S1 N5 C13 O5 -178.31(16) . . . . ?
S1 N5 C13 C14 0.7(2) . . . . ?
S1 C19 C18 C17 178.66(16) . . . . ?
O3 S1 N5 C13 -115.29(14) . . . . ?
O3 S1 C19 C14 115.72(14) . . . . ?
O3 S1 C19 C18 -63.0(2) . . . . ?
O4 S1 N5 C13 114.18(15) . . . . ?
O4 S1 C19 C14 -114.06(14) . . . . ?
O4 S1 C19 C18 67.3(2) . . . . ?
N5 S1 C19 C14 -0.15(14) . . . . ?
N5 S1 C19 C18 -178.82(19) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C14 C19 C18 C17 0.2(3) . . . . ?
C15 C14 C19 S1 -179.20(15) . . . . ?
C15 C14 C19 C18 -0.4(3) . . . . ?
C15 C14 C13 O5 -2.1(3) . . . . ?
C15 C14 C13 N5 178.88(19) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C19 S1 N5 C13 -0.35(15) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C19 C14 C13 O5 178.21(18) . . . . ?
C19 C14 C13 N5 -0.9(2) . . . . ?
C19 C18 C17 C16 0.6(3) . . . . ?
C13 C14 C15 C16 -179.87(19) . . . . ?
C13 C14 C19 S1 0.55(19) . . . . ?
C13 C14 C19 C18 179.35(17) . . . . ?

_olex2_date_sample_data_collection 2015-05-13
_olex2_submission_special_instructions 'No special instructions were received'
