# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_15059_0m
_database_code_depnum_ccdc_archive 'CCDC 1452828'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'SMT-SAC salt'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N5 O5 S2'
_chemical_formula_weight         461.51

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'
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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   10.4993(5)
_cell_length_b                   16.0117(8)
_cell_length_c                   25.1481(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4227.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    147
_cell_measurement_theta_min      0.70
_cell_measurement_theta_max      25

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    2.658
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.4652
_exptl_absorpt_correction_T_max  0.5449
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2 platform CCD'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23853
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         5.34
_diffrn_reflns_theta_max         74.47
_reflns_number_total             4250
_reflns_number_gt                4203
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex 2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0404P)²+2.7874P] 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         4250
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
S2 S 0.28379(3) 0.09557(2) 0.517179(13) 0.01524(10) Uani 1 1 d . . .
O27 O -0.05075(10) 0.10212(6) 0.47494(4) 0.0197(2) Uani 1 1 d . . .
C27 C 0.06639(14) 0.09185(8) 0.48046(5) 0.0153(3) Uani 1 1 d . . .
O22 O 0.32593(10) 0.03533(6) 0.55562(4) 0.0226(2) Uani 1 1 d . . .
O21 O 0.35522(10) 0.17215(6) 0.51491(4) 0.0222(2) Uani 1 1 d . . .
N8 N 0.13250(11) 0.11583(7) 0.52348(5) 0.0162(2) Uani 1 1 d . . .
C21 C 0.27306(13) 0.04956(8) 0.45318(6) 0.0160(3) Uani 1 1 d . . .
C26 C 0.14614(13) 0.05187(8) 0.43835(5) 0.0155(3) Uani 1 1 d . . .
C22 C 0.36688(14) 0.01506(9) 0.42139(6) 0.0203(3) Uani 1 1 d . . .
C23 C 0.32760(16) -0.01802(9) 0.37285(6) 0.0229(3) Uani 1 1 d . . .
C25 C 0.10745(15) 0.01937(9) 0.38989(6) 0.0195(3) Uani 1 1 d . . .
C24 C 0.20028(16) -0.01569(9) 0.35705(6) 0.0222(3) Uani 1 1 d . . .
S1 S 0.07836(3) 0.19905(2) 0.664461(14) 0.01901(11) Uani 1 1 d . . .
O12 O 0.20341(11) 0.17015(7) 0.65060(5) 0.0278(3) Uani 1 1 d . . .
N1 N 0.00028(12) 0.18537(8) 0.60779(5) 0.0181(3) Uani 1 1 d . . .
N3 N -0.17379(11) 0.17606(7) 0.55249(5) 0.0138(2) Uani 1 1 d . . .
C2 C -0.12675(14) 0.19895(8) 0.60036(5) 0.0153(3) Uani 1 1 d . . .
O11 O 0.01063(12) 0.15833(7) 0.70642(4) 0.0284(3) Uani 1 1 d . . .
C4 C -0.29758(13) 0.18884(8) 0.54042(6) 0.0149(3) Uani 1 1 d . . .
N7 N -0.19704(12) 0.23270(7) 0.63829(5) 0.0181(3) Uani 1 1 d . . .
C5 C -0.37532(14) 0.22297(9) 0.57895(6) 0.0180(3) Uani 1 1 d . . .
C11 C 0.08507(14) 0.30541(9) 0.67754(6) 0.0176(3) Uani 1 1 d . . .
C13 C 0.19261(15) 0.43652(10) 0.66545(6) 0.0221(3) Uani 1 1 d . . .
N14 N 0.11251(17) 0.55903(9) 0.70886(6) 0.0314(3) Uani 1 1 d . . .
C14 C 0.10479(15) 0.47559(9) 0.69947(6) 0.0200(3) Uani 1 1 d . . .
C41 C -0.33932(14) 0.16636(9) 0.48582(6) 0.0177(3) Uani 1 1 d . . .
C12 C 0.18344(15) 0.35227(10) 0.65482(6) 0.0207(3) Uani 1 1 d . . .
C17 C -0.00345(14) 0.34313(9) 0.71117(5) 0.0183(3) Uani 1 1 d . . .
C61 C -0.39982(18) 0.27797(12) 0.67230(7) 0.0285(4) Uani 1 1 d . . .
C15 C 0.00732(15) 0.42720(9) 0.72262(6) 0.0193(3) Uani 1 1 d . . .
C6 C -0.32137(15) 0.24349(9) 0.62780(6) 0.0186(3) Uani 1 1 d . . .
H17 H -0.0725(17) 0.3096(11) 0.7256(7) 0.016(4) Uiso 1 1 d . . .
H12 H 0.245(2) 0.3281(13) 0.6313(8) 0.028(5) Uiso 1 1 d . . .
H25 H 0.0192(19) 0.0195(12) 0.3798(7) 0.024(5) Uiso 1 1 d . . .
H13 H 0.259(2) 0.4706(13) 0.6498(8) 0.033(5) Uiso 1 1 d . . .
H5 H -0.465(2) 0.2313(12) 0.5721(7) 0.027(5) Uiso 1 1 d . . .
H15 H -0.0551(18) 0.4535(11) 0.7477(8) 0.024(5) Uiso 1 1 d . . .
H23 H 0.3921(19) -0.0464(12) 0.3505(8) 0.026(5) Uiso 1 1 d . . .
H24 H 0.1786(19) -0.0399(12) 0.3226(8) 0.027(5) Uiso 1 1 d . . .
H22 H 0.4535(19) 0.0151(12) 0.4340(7) 0.024(5) Uiso 1 1 d . . .
H41C H -0.427(2) 0.1722(14) 0.4832(8) 0.035(6) Uiso 1 1 d . . .
H41B H -0.299(2) 0.2045(13) 0.4611(9) 0.034(5) Uiso 1 1 d . . .
H3 H -0.123(2) 0.1506(13) 0.5267(8) 0.031(5) Uiso 1 1 d . . .
H41A H -0.312(2) 0.1098(14) 0.4750(8) 0.036(6) Uiso 1 1 d . . .
H14B H 0.065(2) 0.5814(13) 0.7316(8) 0.028(5) Uiso 1 1 d . . .
H14A H 0.168(2) 0.5883(14) 0.6913(9) 0.038(6) Uiso 1 1 d . . .
H61C H -0.410(3) 0.2381(17) 0.6995(11) 0.059(8) Uiso 1 1 d . . .
H61B H -0.481(3) 0.2972(16) 0.6602(10) 0.053(7) Uiso 1 1 d . . .
H61A H -0.360(3) 0.3263(17) 0.6889(10) 0.055(7) Uiso 1 1 d . . .
H1 H 0.044(2) 0.1645(14) 0.5805(9) 0.036(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
S2 O22 1.4355(11) . ?
S2 O21 1.4385(11) . ?
S2 N8 1.6290(12) . ?
S2 C21 1.7735(15) . ?
O27 C27 1.2486(18) . ?
C27 N8 1.3415(19) . ?
C27 C26 1.4942(19) . ?
C21 C22 1.384(2) . ?
C21 C26 1.384(2) . ?
C26 C25 1.386(2) . ?
C22 C23 1.393(2) . ?
C23 C24 1.395(2) . ?
C25 C24 1.395(2) . ?
S1 O11 1.4298(12) . ?
S1 O12 1.4351(12) . ?
S1 N1 1.6586(12) . ?
S1 C11 1.7359(14) . ?
N1 C2 1.3642(19) . ?
N3 C4 1.3503(18) . ?
N3 C2 1.3519(18) . ?
C2 N7 1.3216(18) . ?
C4 C5 1.380(2) . ?
C4 C41 1.486(2) . ?
N7 C6 1.343(2) . ?
C5 C6 1.392(2) . ?
C11 C17 1.394(2) . ?
C11 C12 1.399(2) . ?
C13 C12 1.378(2) . ?
C13 C14 1.405(2) . ?
N14 C14 1.359(2) . ?
C14 C15 1.409(2) . ?
C17 C15 1.381(2) . ?
C61 C6 1.495(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O22 S2 O21 116.03(7) . . ?
O22 S2 N8 111.65(7) . . ?
O21 S2 N8 110.03(6) . . ?
O22 S2 C21 110.59(6) . . ?
O21 S2 C21 110.56(6) . . ?
N8 S2 C21 96.27(6) . . ?
O27 C27 N8 124.17(13) . . ?
O27 C27 C26 121.97(13) . . ?
N8 C27 C26 113.85(12) . . ?
C27 N8 S2 111.66(10) . . ?
C22 C21 C26 122.70(14) . . ?
C22 C21 S2 130.16(12) . . ?
C26 C21 S2 107.13(10) . . ?
C21 C26 C25 120.61(13) . . ?
C21 C26 C27 111.09(12) . . ?
C25 C26 C27 128.30(13) . . ?
C21 C22 C23 116.57(14) . . ?
C22 C23 C24 121.54(14) . . ?
C26 C25 C24 117.82(14) . . ?
C23 C24 C25 120.76(14) . . ?
O11 S1 O12 119.16(7) . . ?
O11 S1 N1 109.15(7) . . ?
O12 S1 N1 101.59(7) . . ?
O11 S1 C11 109.13(7) . . ?
O12 S1 C11 108.98(7) . . ?
N1 S1 C11 108.21(7) . . ?
C2 N1 S1 125.44(10) . . ?
C4 N3 C2 120.72(12) . . ?
N7 C2 N3 123.34(13) . . ?
N7 C2 N1 120.81(13) . . ?
N3 C2 N1 115.85(12) . . ?
N3 C4 C5 118.13(13) . . ?
N3 C4 C41 117.07(12) . . ?
C5 C4 C41 124.79(13) . . ?
C2 N7 C6 116.97(13) . . ?
C4 C5 C6 118.20(13) . . ?
C17 C11 C12 120.51(13) . . ?
C17 C11 S1 120.86(11) . . ?
C12 C11 S1 118.61(12) . . ?
C12 C13 C14 120.53(14) . . ?
N14 C14 C13 120.30(15) . . ?
N14 C14 C15 120.79(15) . . ?
C13 C14 C15 118.90(14) . . ?
C13 C12 C11 119.82(14) . . ?
C15 C17 C11 119.61(14) . . ?
C17 C15 C14 120.61(14) . . ?
N7 C6 C5 122.59(13) . . ?
N7 C6 C61 115.85(14) . . ?
C5 C6 C61 121.56(14) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        74.47
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_123k
_database_code_depnum_ccdc_archive 'CCDC 1511452'
_audit_update_record             
;
2016-10-25 deposited with the CCDC.
2018-08-13 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 H19 N5 O5 S2'
_chemical_formula_weight         461.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0291(2)
_cell_length_b                   17.5002(4)
_cell_length_c                   14.6076(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.8270(10)
_cell_angle_gamma                90.00
_cell_volume                     1953.97(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    128(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    2.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_T_max  0.7241
_exptl_absorpt_process_details   'multi-scan absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      128(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            13328
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.06
_diffrn_reflns_theta_max         67.09
_reflns_number_total             3467
_reflns_number_gt                2890
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0343P)²+2.3497P] 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         3467
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
S1 S -0.29775(8) 0.06167(4) 0.20224(4) 0.01689(17) Uani 1 1 d . . .
O1 O -0.3586(3) 0.13503(10) 0.22484(14) 0.0255(5) Uani 1 1 d . . .
O2 O -0.4284(2) 0.01399(11) 0.13727(13) 0.0231(4) Uani 1 1 d . . .
N1 N -0.1068(3) -0.08981(12) 0.25232(15) 0.0163(5) Uani 1 1 d . . .
N2 N -0.2167(3) 0.02312(12) 0.30635(15) 0.0166(5) Uani 1 1 d . . .
N3 N 0.2495(3) 0.10454(14) 0.00952(18) 0.0218(5) Uani 1 1 d . . .
N4 N -0.1248(3) -0.07573(12) 0.40948(15) 0.0150(5) Uani 1 1 d . . .
C1 C 0.0081(4) -0.20597(15) 0.20552(19) 0.0209(6) Uani 1 1 d . . .
H1A H -0.0222 -0.1778 0.1447 0.031 Uiso 1 1 calc R . .
H1B H -0.0585 -0.2538 0.1965 0.031 Uiso 1 1 calc R . .
H1C H 0.1336 -0.2175 0.2265 0.031 Uiso 1 1 calc R . .
C2 C -0.0351(3) -0.15879(14) 0.27972(18) 0.0158(5) Uani 1 1 d . . .
C3 C -0.1501(3) -0.04801(14) 0.31872(17) 0.0147(5) Uani 1 1 d . . .
C4 C -0.1310(3) 0.07638(14) 0.14853(18) 0.0159(5) Uani 1 1 d . . .
C5 C 0.0434(4) 0.08649(14) 0.20211(18) 0.0187(6) Uani 1 1 d . . .
C6 C 0.1685(4) 0.09717(15) 0.15636(19) 0.0186(6) Uani 1 1 d . . .
C7 C 0.1221(3) 0.09639(14) 0.05520(18) 0.0176(6) Uani 1 1 d . . .
C8 C -0.0030(3) -0.18757(15) 0.37271(18) 0.0168(5) Uani 1 1 d . . .
C9 C -0.0516(3) -0.14506(14) 0.43839(18) 0.0153(5) Uani 1 1 d . . .
C10 C -0.0354(4) -0.16879(18) 0.53809(19) 0.0206(6) Uani 1 1 d . . .
C11 C -0.1801(4) 0.07871(15) 0.04822(19) 0.0201(6) Uani 1 1 d . . .
C12 C -0.0543(4) 0.08872(15) 0.00286(19) 0.0198(6) Uani 1 1 d . . .
S2 S -0.53715(8) -0.18365(4) 0.56094(4) 0.01632(17) Uani 1 1 d . . .
O3 O -0.6512(2) -0.24469(10) 0.56649(13) 0.0226(4) Uani 1 1 d . . .
O4 O -0.3675(2) -0.18128(11) 0.63126(12) 0.0218(4) Uani 1 1 d . . .
O5 O -0.7401(2) 0.00279(10) 0.45878(13) 0.0205(4) Uani 1 1 d . . .
N5 N -0.6371(3) -0.09936(13) 0.55800(16) 0.0184(5) Uani 1 1 d . . .
C13 C -0.5335(4) -0.13083(15) 0.26143(19) 0.0197(6) Uani 1 1 d . . .
C14 C -0.6013(4) -0.08046(16) 0.31421(18) 0.0188(6) Uani 1 1 d . . .
C15 C -0.5971(3) -0.10176(14) 0.40616(18) 0.0160(5) Uani 1 1 d . . .
C16 C -0.5246(3) -0.17178(14) 0.44325(17) 0.0149(5) Uani 1 1 d . . .
C17 C -0.4639(4) -0.20100(16) 0.29932(19) 0.0209(6) Uani 1 1 d . . .
C18 C -0.4579(4) -0.22280(15) 0.39203(19) 0.0186(6) Uani 1 1 d . . .
C19 C -0.6660(3) -0.05954(15) 0.47422(18) 0.0169(5) Uani 1 1 d . . .
H12 H -0.091(4) 0.0857(15) -0.068(2) 0.017(7) Uiso 1 1 d . . .
H5 H 0.080(4) 0.0874(16) 0.272(2) 0.023(8) Uiso 1 1 d . . .
H13 H -0.542(4) -0.1183(16) 0.197(2) 0.018(7) Uiso 1 1 d . . .
H11 H -0.296(4) 0.0709(17) 0.013(2) 0.028(8) Uiso 1 1 d . . .
H8 H 0.056(4) -0.2348(17) 0.390(2) 0.022(8) Uiso 1 1 d . . .
H3B H 0.342(5) 0.0855(18) 0.041(2) 0.029(9) Uiso 1 1 d . . .
H5A H -0.661(4) -0.0856(17) 0.605(2) 0.024(8) Uiso 1 1 d . . .
H3A H 0.212(4) 0.0904(17) -0.056(2) 0.024(8) Uiso 1 1 d . . .
H4 H -0.153(4) -0.0505(17) 0.447(2) 0.022(9) Uiso 1 1 d . . .
H10C H 0.032(5) -0.212(2) 0.550(3) 0.045(10) Uiso 1 1 d . . .
H14 H -0.648(4) -0.0349(19) 0.286(2) 0.031(9) Uiso 1 1 d . . .
H17 H -0.415(4) -0.2353(18) 0.263(2) 0.031(9) Uiso 1 1 d . . .
H6 H 0.289(4) 0.1023(18) 0.192(2) 0.033(9) Uiso 1 1 d . . .
H10B H 0.026(5) -0.133(2) 0.583(3) 0.055(12) Uiso 1 1 d . . .
H10A H -0.145(5) -0.178(2) 0.546(3) 0.045(10) Uiso 1 1 d . . .
H18 H -0.413(4) -0.2692(17) 0.421(2) 0.023(8) 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 1.4450(19) . ?
S1 O1 1.4471(19) . ?
S1 N2 1.608(2) . ?
S1 C4 1.766(3) . ?
N1 C3 1.343(3) . ?
N1 C2 1.345(3) . ?
N2 C3 1.345(3) . ?
N3 C7 1.389(3) . ?
N3 H3B 0.81(3) . ?
N3 H3A 0.94(3) . ?
N4 C9 1.358(3) . ?
N4 C3 1.367(3) . ?
N4 H4 0.79(3) . ?
C1 C2 1.486(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C8 1.397(4) . ?
C4 C5 1.390(4) . ?
C4 C11 1.397(4) . ?
C5 C6 1.379(4) . ?
C5 H5 0.98(3) . ?
C6 C7 1.409(4) . ?
C6 H6 0.95(3) . ?
C7 C12 1.395(4) . ?
C8 C9 1.362(4) . ?
C8 H8 0.95(3) . ?
C9 C10 1.481(3) . ?
C10 H10C 0.91(4) . ?
C10 H10B 0.94(4) . ?
C10 H10A 0.94(4) . ?
C11 C12 1.378(4) . ?
C11 H11 0.93(3) . ?
C12 H12 0.99(3) . ?
S2 O3 1.4255(19) . ?
S2 O4 1.4337(18) . ?
S2 N5 1.673(2) . ?
S2 C16 1.765(3) . ?
O5 C19 1.230(3) . ?
N5 C19 1.365(3) . ?
N5 H5A 0.81(3) . ?
C13 C14 1.387(4) . ?
C13 C17 1.392(4) . ?
C13 H13 0.94(3) . ?
C14 C15 1.384(4) . ?
C14 H14 0.92(3) . ?
C15 C16 1.393(4) . ?
C15 C19 1.475(4) . ?
C16 C18 1.374(4) . ?
C17 C18 1.393(4) . ?
C17 H17 0.96(3) . ?
C18 H18 0.93(3) . ?

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 O1 115.74(12) . . ?
O2 S1 N2 112.41(11) . . ?
O1 S1 N2 102.92(11) . . ?
O2 S1 C4 106.80(12) . . ?
O1 S1 C4 109.07(12) . . ?
N2 S1 C4 109.82(12) . . ?
C3 N1 C2 117.1(2) . . ?
C3 N2 S1 123.00(18) . . ?
C7 N3 H3B 111(2) . . ?
C7 N3 H3A 113.7(19) . . ?
H3B N3 H3A 115(3) . . ?
C9 N4 C3 122.7(2) . . ?
C9 N4 H4 118(2) . . ?
C3 N4 H4 119(2) . . ?
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 . . ?
N1 C2 C8 123.2(2) . . ?
N1 C2 C1 117.1(2) . . ?
C8 C2 C1 119.6(2) . . ?
N1 C3 N2 126.0(2) . . ?
N1 C3 N4 120.8(2) . . ?
N2 C3 N4 113.2(2) . . ?
C5 C4 C11 119.9(2) . . ?
C5 C4 S1 122.6(2) . . ?
C11 C4 S1 117.5(2) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 118.5(17) . . ?
C4 C5 H5 121.4(17) . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6 121(2) . . ?
C7 C6 H6 118(2) . . ?
N3 C7 C12 121.3(2) . . ?
N3 C7 C6 120.4(2) . . ?
C12 C7 C6 118.3(2) . . ?
C9 C8 C2 118.7(2) . . ?
C9 C8 H8 121.1(18) . . ?
C2 C8 H8 120.1(18) . . ?
N4 C9 C8 117.3(2) . . ?
N4 C9 C10 117.1(2) . . ?
C8 C9 C10 125.6(2) . . ?
C9 C10 H10C 107(2) . . ?
C9 C10 H10B 112(2) . . ?
H10C C10 H10B 105(3) . . ?
C9 C10 H10A 112(2) . . ?
H10C C10 H10A 111(3) . . ?
H10B C10 H10A 110(3) . . ?
C12 C11 C4 119.7(3) . . ?
C12 C11 H11 121.0(19) . . ?
C4 C11 H11 119.2(19) . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 H12 118.1(16) . . ?
C7 C12 H12 120.4(16) . . ?
O3 S2 O4 117.84(11) . . ?
O3 S2 N5 110.52(11) . . ?
O4 S2 N5 109.62(11) . . ?
O3 S2 C16 111.90(11) . . ?
O4 S2 C16 111.67(12) . . ?
N5 S2 C16 92.37(11) . . ?
C19 N5 S2 114.93(18) . . ?
C19 N5 H5A 126(2) . . ?
S2 N5 H5A 119(2) . . ?
C14 C13 C17 121.2(3) . . ?
C14 C13 H13 118.9(17) . . ?
C17 C13 H13 119.9(17) . . ?
C15 C14 C13 118.1(3) . . ?
C15 C14 H14 124(2) . . ?
C13 C14 H14 118(2) . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 C19 128.0(2) . . ?
C16 C15 C19 112.1(2) . . ?
C18 C16 C15 123.1(2) . . ?
C18 C16 S2 127.0(2) . . ?
C15 C16 S2 109.91(19) . . ?
C13 C17 C18 121.2(3) . . ?
C13 C17 H17 120.8(19) . . ?
C18 C17 H17 118.0(19) . . ?
C16 C18 C17 116.6(2) . . ?
C16 C18 H18 118.8(19) . . ?
C17 C18 H18 124.6(19) . . ?
O5 C19 N5 123.8(2) . . ?
O5 C19 C15 125.5(2) . . ?
N5 C19 C15 110.6(2) . . ?

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
O2 S1 N2 C3 52.2(2) . . . . ?
O1 S1 N2 C3 177.4(2) . . . . ?
C4 S1 N2 C3 -66.5(2) . . . . ?
C3 N1 C2 C8 -0.7(4) . . . . ?
C3 N1 C2 C1 178.3(2) . . . . ?
C2 N1 C3 N2 177.3(2) . . . . ?
C2 N1 C3 N4 -1.2(4) . . . . ?
S1 N2 C3 N1 15.2(4) . . . . ?
S1 N2 C3 N4 -166.15(18) . . . . ?
C9 N4 C3 N1 1.7(4) . . . . ?
C9 N4 C3 N2 -177.0(2) . . . . ?
O2 S1 C4 C5 -148.9(2) . . . . ?
O1 S1 C4 C5 85.3(2) . . . . ?
N2 S1 C4 C5 -26.8(2) . . . . ?
O2 S1 C4 C11 31.9(2) . . . . ?
O1 S1 C4 C11 -93.8(2) . . . . ?
N2 S1 C4 C11 154.1(2) . . . . ?
C11 C4 C5 C6 -1.4(4) . . . . ?
S1 C4 C5 C6 179.5(2) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C5 C6 C7 N3 -177.8(2) . . . . ?
C5 C6 C7 C12 3.4(4) . . . . ?
N1 C2 C8 C9 2.2(4) . . . . ?
C1 C2 C8 C9 -176.8(2) . . . . ?
C3 N4 C9 C8 -0.1(4) . . . . ?
C3 N4 C9 C10 -178.7(2) . . . . ?
C2 C8 C9 N4 -1.7(4) . . . . ?
C2 C8 C9 C10 176.7(3) . . . . ?
C5 C4 C11 C12 2.0(4) . . . . ?
S1 C4 C11 C12 -178.9(2) . . . . ?
C4 C11 C12 C7 0.2(4) . . . . ?
N3 C7 C12 C11 178.3(2) . . . . ?
C6 C7 C12 C11 -2.9(4) . . . . ?
O3 S2 N5 C19 -114.34(19) . . . . ?
O4 S2 N5 C19 114.15(19) . . . . ?
C16 S2 N5 C19 0.1(2) . . . . ?
C17 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C13 C14 C15 C19 -177.7(2) . . . . ?
C14 C15 C16 C18 -1.1(4) . . . . ?
C19 C15 C16 C18 177.4(2) . . . . ?
C14 C15 C16 S2 -179.9(2) . . . . ?
C19 C15 C16 S2 -1.4(3) . . . . ?
O3 S2 C16 C18 -64.7(3) . . . . ?
O4 S2 C16 C18 69.8(3) . . . . ?
N5 S2 C16 C18 -178.0(2) . . . . ?
O3 S2 C16 C15 114.01(19) . . . . ?
O4 S2 C16 C15 -111.45(19) . . . . ?
N5 S2 C16 C15 0.76(19) . . . . ?
C14 C13 C17 C18 -0.8(4) . . . . ?
C15 C16 C18 C17 0.7(4) . . . . ?
S2 C16 C18 C17 179.3(2) . . . . ?
C13 C17 C18 C16 0.3(4) . . . . ?
S2 N5 C19 O5 178.8(2) . . . . ?
S2 N5 C19 C15 -0.9(3) . . . . ?
C14 C15 C19 O5 0.2(4) . . . . ?
C16 C15 C19 O5 -178.3(2) . . . . ?
C14 C15 C19 N5 179.9(2) . . . . ?
C16 C15 C19 N5 1.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        67.09
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.070
