# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1414989'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 N3 O8 S'
_chemical_formula_sum            'C18 H23 N3 O8 S'
_chemical_formula_weight         441.45

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           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_HALL  'P 2yb'

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

_cell_length_a                   9.9041(10)
_cell_length_b                   10.0867(9)
_cell_length_c                   10.6948(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.617(8)
_cell_angle_gamma                90.00
_cell_volume                     1064.94(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_chemical_absolute_configuration .

_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  'Xcalibur, Sapphire3'
_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            8460
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         29.28
_reflns_number_total             4609
_reflns_number_gt                3406
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1189P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_number_reflns         4609
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_restrained_S_all      0.839
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 -0.08292(9) 0.15265(8) 0.43500(8) 0.0523(2) Uani 1 1 d . . .
O3 O -0.1640(3) 0.2687(3) 0.4348(3) 0.0632(7) Uani 1 1 d . . .
O4 O -0.0315(3) 0.1181(2) 0.5745(2) 0.0553(6) Uani 1 1 d . . .
O5 O 0.0479(3) 0.0752(2) 0.8304(2) 0.0548(6) Uani 1 1 d . . .
O7 O -0.0881(2) 0.3155(2) 0.9140(2) 0.0517(6) Uani 1 1 d . . .
O2 O -0.1398(3) 0.0308(3) 0.3866(3) 0.0707(8) Uani 1 1 d . . .
O8 O -0.1160(3) 0.1010(3) 0.9737(3) 0.0663(7) Uani 1 1 d . . .
O6 O 0.3032(3) 0.2177(3) 0.6508(3) 0.0684(7) Uani 1 1 d . . .
C8 C 0.0131(4) 0.2279(3) 0.6547(3) 0.0489(7) Uani 1 1 d . . .
H8A H -0.0644 0.2697 0.6883 0.059 Uiso 1 1 calc R . .
H8B H 0.0585 0.2934 0.6066 0.059 Uiso 1 1 calc R . .
O1 O 0.4767(4) 0.0828(4) 0.6299(4) 0.1064(13) Uani 1 1 d . . .
C5 C 0.0664(4) 0.1876(3) 0.3657(3) 0.0482(8) Uani 1 1 d . . .
C14 C 0.0424(4) 0.2669(3) 0.9544(3) 0.0514(8) Uani 1 1 d . . .
H14 H 0.0757 0.3004 1.0372 0.062 Uiso 1 1 calc R . .
C13 C 0.1402(3) 0.2929(3) 0.8545(3) 0.0482(7) Uani 1 1 d . . .
H13 H 0.1235 0.3792 0.8141 0.058 Uiso 1 1 calc R . .
C16 C -0.1852(4) 0.2253(4) 0.9598(3) 0.0565(9) Uani 1 1 d . . .
N1 N 0.2781(3) 0.2842(4) 0.9165(3) 0.0681(9) Uani 1 1 d . . .
C9 C 0.1095(3) 0.1766(3) 0.7610(3) 0.0464(7) Uani 1 1 d . . .
C4 C 0.0984(4) 0.3150(4) 0.3352(3) 0.0566(8) Uani 1 1 d . . .
H4 H 0.0388 0.3839 0.3482 0.068 Uiso 1 1 calc R . .
C10 C 0.2353(4) 0.1151(4) 0.7135(4) 0.0598(9) Uani 1 1 d . . .
H10A H 0.2937 0.0802 0.7829 0.072 Uiso 1 1 calc R . .
H10B H 0.2106 0.0432 0.6559 0.072 Uiso 1 1 calc R . .
N2 N 0.3520(3) 0.3778(4) 0.9011(4) 0.0732(10) Uani 1 1 d . . .
C11 C 0.4273(4) 0.1896(5) 0.6149(4) 0.0693(12) Uani 1 1 d . . .
C3 C 0.2206(4) 0.3403(4) 0.2848(4) 0.0656(10) Uani 1 1 d . . .
H3 H 0.2420 0.4272 0.2648 0.079 Uiso 1 1 calc R . .
C2 C 0.3110(4) 0.2412(4) 0.2635(3) 0.0621(9) Uani 1 1 d . . .
C15 C 0.0197(4) 0.1183(3) 0.9531(3) 0.0500(8) Uani 1 1 d . . .
H15 H 0.0789 0.0743 1.0182 0.060 Uiso 1 1 calc R . .
C17 C -0.2229(5) 0.2688(5) 1.0871(4) 0.0801(13) Uani 1 1 d . . .
H17A H -0.2697 0.3521 1.0797 0.120 Uiso 1 1 calc R . .
H17B H -0.1423 0.2785 1.1425 0.120 Uiso 1 1 calc R . .
H17C H -0.2808 0.2035 1.1203 0.120 Uiso 1 1 calc R . .
C12 C 0.4907(5) 0.3068(7) 0.5602(4) 0.0908(16) Uani 1 1 d . . .
H12A H 0.4289 0.3802 0.5585 0.136 Uiso 1 1 calc R . .
H12B H 0.5120 0.2867 0.4763 0.136 Uiso 1 1 calc R . .
H12C H 0.5722 0.3294 0.6103 0.136 Uiso 1 1 calc R . .
C18 C -0.3035(4) 0.2128(6) 0.8634(5) 0.0839(13) Uani 1 1 d . . .
H18A H -0.3495 0.2965 0.8543 0.126 Uiso 1 1 calc R . .
H18B H -0.3650 0.1468 0.8899 0.126 Uiso 1 1 calc R . .
H18C H -0.2718 0.1872 0.7845 0.126 Uiso 1 1 calc R . .
C6 C 0.1557(5) 0.0857(4) 0.3462(5) 0.0807(14) Uani 1 1 d . . .
H6 H 0.1347 -0.0009 0.3671 0.097 Uiso 1 1 calc R . .
N3 N 0.4300(5) 0.4564(5) 0.8932(7) 0.126(2) Uani 1 1 d . . .
C1 C 0.4446(5) 0.2698(6) 0.2120(5) 0.0899(15) Uani 1 1 d . . .
H1A H 0.4521 0.3632 0.1968 0.135 Uiso 1 1 calc R . .
H1B H 0.4502 0.2222 0.1348 0.135 Uiso 1 1 calc R . .
H1C H 0.5169 0.2422 0.2715 0.135 Uiso 1 1 calc R . .
C7 C 0.2765(5) 0.1137(5) 0.2953(5) 0.0816(13) Uani 1 1 d . . .
H7 H 0.3360 0.0448 0.2820 0.098 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
S1 O3 1.419(3) . ?
S1 O2 1.431(3) . ?
S1 O4 1.577(3) . ?
S1 C5 1.742(4) . ?
O4 C8 1.448(4) . ?
O5 C9 1.429(4) . ?
O5 C15 1.432(4) . ?
O7 C14 1.417(4) . ?
O7 C16 1.438(4) . ?
O8 C15 1.389(4) . ?
O8 C16 1.431(5) . ?
O6 C11 1.347(5) . ?
O6 C10 1.430(5) . ?
C8 C9 1.516(5) . ?
O1 C11 1.189(6) . ?
C5 C4 1.369(5) . ?
C5 C6 1.383(5) . ?
C14 C15 1.515(5) . ?
C14 C13 1.522(4) . ?
C13 N1 1.472(5) . ?
C13 C9 1.556(4) . ?
C16 C18 1.503(6) . ?
C16 C17 1.506(5) . ?
N1 N2 1.214(5) . ?
C9 C10 1.515(5) . ?
C4 C3 1.388(5) . ?
N2 N3 1.115(5) . ?
C11 C12 1.481(7) . ?
C3 C2 1.373(6) . ?
C2 C7 1.380(7) . ?
C2 C1 1.501(6) . ?
C6 C7 1.383(6) . ?

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
O3 S1 O2 120.11(17) . . ?
O3 S1 O4 108.89(14) . . ?
O2 S1 O4 103.90(15) . . ?
O3 S1 C5 109.35(16) . . ?
O2 S1 C5 110.03(16) . . ?
O4 S1 C5 103.11(15) . . ?
C8 O4 S1 116.81(19) . . ?
C9 O5 C15 112.4(2) . . ?
C14 O7 C16 107.2(3) . . ?
C15 O8 C16 109.5(3) . . ?
C11 O6 C10 117.1(3) . . ?
O4 C8 C9 109.1(3) . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 S1 120.8(3) . . ?
C6 C5 S1 119.3(3) . . ?
O7 C14 C15 102.0(3) . . ?
O7 C14 C13 110.1(3) . . ?
C15 C14 C13 105.5(3) . . ?
N1 C13 C14 107.1(3) . . ?
N1 C13 C9 111.8(3) . . ?
C14 C13 C9 102.6(2) . . ?
O8 C16 O7 105.2(3) . . ?
O8 C16 C18 109.8(3) . . ?
O7 C16 C18 109.0(3) . . ?
O8 C16 C17 108.2(3) . . ?
O7 C16 C17 110.2(3) . . ?
C18 C16 C17 114.1(4) . . ?
N2 N1 C13 116.1(3) . . ?
O5 C9 C10 106.2(3) . . ?
O5 C9 C8 111.4(3) . . ?
C10 C9 C8 111.9(3) . . ?
O5 C9 C13 106.0(2) . . ?
C10 C9 C13 113.6(3) . . ?
C8 C9 C13 107.7(3) . . ?
C5 C4 C3 119.5(3) . . ?
O6 C10 C9 106.9(3) . . ?
N3 N2 N1 173.0(5) . . ?
O1 C11 O6 121.8(4) . . ?
O1 C11 C12 126.4(5) . . ?
O6 C11 C12 111.8(4) . . ?
C4 C3 C2 122.1(4) . . ?
C7 C2 C3 117.4(4) . . ?
C7 C2 C1 120.8(4) . . ?
C3 C2 C1 121.8(4) . . ?
O8 C15 O5 111.7(3) . . ?
O8 C15 C14 105.5(3) . . ?
O5 C15 C14 105.6(3) . . ?
C5 C6 C7 119.5(4) . . ?
C2 C7 C6 121.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.882
_diffrn_reflns_theta_full        29.28
_diffrn_measured_fraction_theta_full 0.882
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1420474'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 N5 O5'
_chemical_formula_sum            'C10 H11 N5 O5'
_chemical_formula_weight         281.24

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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_HALL  'P 2yb'

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

_cell_length_a                   6.5121(16)
_cell_length_b                   6.8206(14)
_cell_length_c                   13.045(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.72(3)
_cell_angle_gamma                90.00
_cell_volume                     578.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_chemical_absolute_configuration .

_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  'Xcalibur, Sapphire3'
_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            3239
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0777
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1747
_reflns_number_gt                1300
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1355P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(3)
_refine_ls_number_reflns         1747
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.2016
_refine_ls_wR_factor_gt          0.1776
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_restrained_S_all      0.911
_refine_ls_shift/su_max          0.080
_refine_ls_shift/su_mean         0.014

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
O2 O 0.9788(6) 0.4029(7) 1.0247(3) 0.0528(12) Uani 1 1 d . . .
O3 O 0.1272(6) 0.4944(6) 0.8053(3) 0.0455(10) Uani 1 1 d . . .
O4 O 0.0377(7) 0.2339(7) 0.6487(4) 0.0593(13) Uani 1 1 d . . .
N1 N 0.4551(7) 0.3550(7) 0.8472(3) 0.0399(11) Uani 1 1 d . . .
O5 O -0.0345(7) 0.8435(8) 0.6092(3) 0.0655(14) Uani 1 1 d . . .
H5 H -0.0700 0.9587 0.6109 0.098 Uiso 1 1 calc R . .
N2 N 0.7517(7) 0.2226(7) 0.9256(4) 0.0420(12) Uani 1 1 d . . .
H2 H 0.8299 0.1230 0.9390 0.050 Uiso 1 1 calc R . .
O1 O 0.5221(7) 0.0300(7) 0.8338(4) 0.0563(12) Uani 1 1 d . . .
C6 C 0.2463(8) 0.3238(9) 0.7926(4) 0.0406(14) Uani 1 1 d . . .
H6 H 0.1790 0.2115 0.8232 0.049 Uiso 1 1 calc R . .
C7 C 0.2424(9) 0.2967(9) 0.6759(4) 0.0418(14) Uani 1 1 d . . .
H7 H 0.3517 0.2141 0.6510 0.050 Uiso 1 1 calc R . .
N4 N 0.4495(8) 0.7612(10) 0.6096(4) 0.0536(14) Uani 1 1 d . . .
C3 C 0.5163(9) 0.5368(9) 0.8822(4) 0.0420(14) Uani 1 1 d . . .
H3 H 0.4335 0.6449 0.8659 0.050 Uiso 1 1 calc R . .
C9 C 0.0559(9) 0.5603(10) 0.7020(4) 0.0453(15) Uani 1 1 d . . .
N3 N 0.4279(8) 0.6134(9) 0.6632(4) 0.0517(14) Uani 1 1 d . . .
C4 C 0.6911(10) 0.5618(8) 0.9387(4) 0.0416(14) Uani 1 1 d . . .
H4 H 0.7302 0.6870 0.9603 0.050 Uiso 1 1 calc R . .
C5 C 0.8186(8) 0.3996(9) 0.9663(4) 0.0406(13) Uani 1 1 d . . .
C1 C 0.5749(9) 0.1881(9) 0.8664(4) 0.0394(13) Uani 1 1 d . . .
N5 N 0.4881(10) 0.8980(12) 0.5652(6) 0.0739(18) Uani 1 1 d . . .
C10 C -0.0953(10) 0.4069(11) 0.6616(5) 0.0553(17) Uani 1 1 d . . .
H10A H -0.1981 0.3807 0.7104 0.066 Uiso 1 1 calc R . .
H10B H -0.1635 0.4468 0.5967 0.066 Uiso 1 1 calc R . .
C8 C 0.2385(9) 0.5107(12) 0.6374(4) 0.0505(16) Uani 1 1 d . . .
H8 H 0.1996 0.5182 0.5637 0.061 Uiso 1 1 calc R . .
C11 C -0.0095(11) 0.7686(10) 0.7114(5) 0.0529(16) Uani 1 1 d . . .
H11A H -0.1380 0.7766 0.7448 0.063 Uiso 1 1 calc R . .
H11B H 0.0943 0.8429 0.7515 0.063 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
O2 C5 1.251(6) . ?
O3 C6 1.414(7) . ?
O3 C9 1.467(7) . ?
O4 C7 1.423(7) . ?
O4 C10 1.480(9) . ?
N1 C3 1.371(8) . ?
N1 C1 1.394(7) . ?
N1 C6 1.509(7) . ?
O5 C11 1.427(8) . ?
O5 H5 0.8200 . ?
N2 C5 1.378(8) . ?
N2 C1 1.364(8) . ?
N2 H2 0.8600 . ?
O1 C1 1.201(7) . ?
C6 C7 1.531(8) . ?
C6 H6 0.9800 . ?
C7 C8 1.543(9) . ?
C7 H7 0.9800 . ?
N4 N5 1.135(10) . ?
N4 N3 1.240(8) . ?
C3 C4 1.326(8) . ?
C3 H3 0.9300 . ?
C9 C11 1.490(9) . ?
C9 C10 1.508(9) . ?
C9 C8 1.539(9) . ?
N3 C8 1.439(8) . ?
C4 C5 1.416(8) . ?
C4 H4 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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 O3 C9 106.7(4) . . ?
C7 O4 C10 106.1(5) . . ?
C3 N1 C1 122.1(5) . . ?
C3 N1 C6 121.2(5) . . ?
C1 N1 C6 116.5(5) . . ?
C11 O5 H5 109.5 . . ?
C5 N2 C1 127.1(5) . . ?
C5 N2 H2 116.4 . . ?
C1 N2 H2 116.4 . . ?
O3 C6 N1 108.2(4) . . ?
O3 C6 C7 104.0(4) . . ?
N1 C6 C7 116.3(5) . . ?
O3 C6 H6 109.4 . . ?
N1 C6 H6 109.4 . . ?
C7 C6 H6 109.3 . . ?
O4 C7 C6 103.9(5) . . ?
O4 C7 C8 102.0(5) . . ?
C6 C7 C8 102.0(4) . . ?
O4 C7 H7 115.7 . . ?
C6 C7 H7 115.7 . . ?
C8 C7 H7 115.7 . . ?
N5 N4 N3 173.2(7) . . ?
C4 C3 N1 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
N1 C3 H3 119.3 . . ?
O3 C9 C11 107.0(5) . . ?
O3 C9 C10 105.6(5) . . ?
C11 C9 C10 120.5(6) . . ?
O3 C9 C8 103.0(4) . . ?
C11 C9 C8 119.3(6) . . ?
C10 C9 C8 99.6(5) . . ?
N4 N3 C8 113.0(5) . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
O2 C5 N2 118.8(6) . . ?
O2 C5 C4 126.4(6) . . ?
N2 C5 C4 114.8(4) . . ?
O1 C1 N1 121.7(5) . . ?
O1 C1 N2 124.5(6) . . ?
N1 C1 N2 113.7(5) . . ?
O4 C10 C9 102.7(5) . . ?
O4 C10 H10A 111.2 . . ?
C9 C10 H10A 111.2 . . ?
O4 C10 H10B 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
N3 C8 C9 116.5(6) . . ?
N3 C8 C7 112.9(5) . . ?
C9 C8 C7 91.5(5) . . ?
N3 C8 H8 111.5 . . ?
C9 C8 H8 111.5 . . ?
C7 C8 H8 111.5 . . ?
O5 C11 C9 106.3(5) . . ?
O5 C11 H11A 110.5 . . ?
C9 C11 H11A 110.5 . . ?
O5 C11 H11B 110.5 . . ?
C9 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?

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
C9 O3 C6 N1 125.0(5) . . . . ?
C9 O3 C6 C7 0.8(5) . . . . ?
C3 N1 C6 O3 -11.7(7) . . . . ?
C1 N1 C6 O3 163.8(5) . . . . ?
C3 N1 C6 C7 104.8(6) . . . . ?
C1 N1 C6 C7 -79.6(6) . . . . ?
C10 O4 C7 C6 71.0(5) . . . . ?
C10 O4 C7 C8 -34.8(6) . . . . ?
O3 C6 C7 O4 -71.9(5) . . . . ?
N1 C6 C7 O4 169.3(5) . . . . ?
O3 C6 C7 C8 33.9(6) . . . . ?
N1 C6 C7 C8 -85.0(6) . . . . ?
C1 N1 C3 C4 -1.9(8) . . . . ?
C6 N1 C3 C4 173.5(5) . . . . ?
C6 O3 C9 C11 -162.1(5) . . . . ?
C6 O3 C9 C10 68.5(6) . . . . ?
C6 O3 C9 C8 -35.5(6) . . . . ?
N5 N4 N3 C8 -175(6) . . . . ?
N1 C3 C4 C5 -1.2(9) . . . . ?
C1 N2 C5 O2 175.4(6) . . . . ?
C1 N2 C5 C4 -2.9(8) . . . . ?
C3 C4 C5 O2 -174.8(6) . . . . ?
C3 C4 C5 N2 3.3(8) . . . . ?
C3 N1 C1 O1 -178.5(6) . . . . ?
C6 N1 C1 O1 6.0(8) . . . . ?
C3 N1 C1 N2 2.3(7) . . . . ?
C6 N1 C1 N2 -173.2(5) . . . . ?
C5 N2 C1 O1 -179.0(6) . . . . ?
C5 N2 C1 N1 0.2(8) . . . . ?
C7 O4 C10 C9 -2.4(6) . . . . ?
O3 C9 C10 O4 -68.1(6) . . . . ?
C11 C9 C10 O4 170.9(6) . . . . ?
C8 C9 C10 O4 38.5(6) . . . . ?
N4 N3 C8 C9 -95.3(7) . . . . ?
N4 N3 C8 C7 160.7(6) . . . . ?
O3 C9 C8 N3 -64.1(7) . . . . ?
C11 C9 C8 N3 54.2(8) . . . . ?
C10 C9 C8 N3 -172.6(6) . . . . ?
O3 C9 C8 C7 52.5(5) . . . . ?
C11 C9 C8 C7 170.8(5) . . . . ?
C10 C9 C8 C7 -56.0(5) . . . . ?
O4 C7 C8 N3 175.7(5) . . . . ?
C6 C7 C8 N3 68.5(6) . . . . ?
O4 C7 C8 C9 56.0(5) . . . . ?
C6 C7 C8 C9 -51.2(5) . . . . ?
O3 C9 C11 O5 167.4(5) . . . . ?
C10 C9 C11 O5 -72.2(7) . . . . ?
C8 C9 C11 O5 51.2(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.053
