# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_azo-metossi
_database_code_depnum_ccdc_archive 'CCDC 1478445'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2016-06-24 downloaded from the CCDC.
;
_audit_creation_date             06/30/2014

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Compound 5a'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N4 O S'
_chemical_formula_weight         288.37

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   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                   15.239(4)
_cell_length_b                   5.9523(15)
_cell_length_c                   16.588(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.134(3)
_cell_angle_gamma                90.00
_cell_volume                     1421.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    223
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.04

_exptl_crystal_description       plates
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9241
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11807
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         28.26
_reflns_number_total             3393
_reflns_number_gt                2764
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0570P)²+0.3058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3393
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.20885(3) 0.54498(6) 0.47258(2) 0.04475(13) Uani 1 1 d . . .
N1 N 0.11563(9) 0.4434(2) 0.58008(8) 0.0482(3) Uani 1 1 d . . .
N2 N 0.13009(10) 0.1621(2) 0.48681(8) 0.0518(3) Uani 1 1 d . . .
N3 N 0.25502(9) 0.3258(2) 0.34444(8) 0.0479(3) Uani 1 1 d . . .
N4 N 0.29240(9) 0.5139(2) 0.33793(8) 0.0456(3) Uani 1 1 d . . .
O1 O 0.43409(10) 0.5743(2) 0.06962(9) 0.0702(4) Uani 1 1 d . . .
C1 C 0.14532(10) 0.3684(2) 0.51781(9) 0.0428(3) Uani 1 1 d . . .
C2 C 0.16971(13) 0.1374(3) 0.42519(10) 0.0536(4) Uani 1 1 d . . .
H2 H 0.1664 0.0017 0.3965 0.064 Uiso 1 1 calc R . .
C3 C 0.21475(11) 0.3184(3) 0.40659(9) 0.0462(3) Uani 1 1 d . . .
C4 C 0.32994(10) 0.5212(3) 0.27028(9) 0.0422(3) Uani 1 1 d . . .
C5 C 0.37672(11) 0.7155(3) 0.26246(10) 0.0500(4) Uani 1 1 d . . .
H5 H 0.3838 0.8305 0.3020 0.060 Uiso 1 1 calc R . .
C6 C 0.41319(11) 0.7411(3) 0.19659(11) 0.0521(4) Uani 1 1 d . . .
H6 H 0.4446 0.8720 0.1922 0.062 Uiso 1 1 calc R . .
C7 C 0.40249(11) 0.5710(3) 0.13751(10) 0.0489(4) Uani 1 1 d . . .
C8 C 0.35657(11) 0.3742(3) 0.14534(11) 0.0531(4) Uani 1 1 d . . .
H8 H 0.3501 0.2590 0.1060 0.064 Uiso 1 1 calc R . .
C9 C 0.32082(11) 0.3490(3) 0.21057(10) 0.0490(4) Uani 1 1 d . . .
H9 H 0.2903 0.2168 0.2152 0.059 Uiso 1 1 calc R . .
C10 C 0.47452(16) 0.7742(4) 0.05196(14) 0.0767(6) Uani 1 1 d . . .
H10A H 0.4940 0.7516 0.0031 0.115 Uiso 1 1 calc R . .
H10B H 0.5273 0.8132 0.1003 0.115 Uiso 1 1 calc R . .
H10C H 0.4297 0.8935 0.0405 0.115 Uiso 1 1 calc R . .
C11 C 0.06853(12) 0.2986(3) 0.62416(11) 0.0539(4) Uani 1 1 d . . .
H11A H 0.1091 0.1785 0.6544 0.065 Uiso 1 1 calc R . .
H11B H 0.0127 0.2336 0.5844 0.065 Uiso 1 1 calc R . .
C12 C 0.04525(12) 0.4566(3) 0.68561(12) 0.0605(5) Uani 1 1 d . . .
H12A H -0.0173 0.5148 0.6610 0.073 Uiso 1 1 calc R . .
H12B H 0.0502 0.3803 0.7386 0.073 Uiso 1 1 calc R . .
C13 C 0.11570(13) 0.6438(3) 0.70091(12) 0.0636(5) Uani 1 1 d . . .
H13A H 0.1726 0.6043 0.7460 0.076 Uiso 1 1 calc R . .
H13B H 0.0913 0.7819 0.7164 0.076 Uiso 1 1 calc R . .
C14 C 0.13280(13) 0.6692(3) 0.61622(11) 0.0545(4) Uani 1 1 d . . .
H14A H 0.0903 0.7771 0.5798 0.065 Uiso 1 1 calc R . .
H14B H 0.1961 0.7163 0.6246 0.065 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 C1 1.7552(15) . ?
S1 C3 1.7579(16) . ?
N1 C1 1.3331(19) . ?
N1 C14 1.460(2) . ?
N1 C11 1.4618(19) . ?
N2 C1 1.322(2) . ?
N2 C2 1.355(2) . ?
N3 N4 1.2764(18) . ?
N3 C3 1.3624(19) . ?
N4 C4 1.4174(19) . ?
O1 C7 1.362(2) . ?
O1 C10 1.414(2) . ?
C2 C3 1.366(2) . ?
C4 C5 1.387(2) . ?
C4 C9 1.400(2) . ?
C5 C6 1.387(2) . ?
C6 C7 1.381(2) . ?
C7 C8 1.392(2) . ?
C8 C9 1.370(2) . ?
C11 C12 1.512(3) . ?
C12 C13 1.510(3) . ?
C13 C14 1.518(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
C1 S1 C3 87.40(7) . . ?
C1 N1 C14 124.44(13) . . ?
C1 N1 C11 122.51(14) . . ?
C14 N1 C11 112.87(13) . . ?
C1 N2 C2 109.24(13) . . ?
N4 N3 C3 114.64(13) . . ?
N3 N4 C4 113.65(13) . . ?
C7 O1 C10 118.64(15) . . ?
N2 C1 N1 123.45(13) . . ?
N2 C1 S1 116.17(11) . . ?
N1 C1 S1 120.38(12) . . ?
N2 C2 C3 117.76(15) . . ?
N3 C3 C2 125.52(14) . . ?
N3 C3 S1 125.01(11) . . ?
C2 C3 S1 109.42(12) . . ?
C5 C4 C9 118.63(14) . . ?
C5 C4 N4 116.94(14) . . ?
C9 C4 N4 124.42(13) . . ?
C4 C5 C6 121.09(15) . . ?
C7 C6 C5 119.58(15) . . ?
O1 C7 C6 125.78(15) . . ?
O1 C7 C8 114.44(15) . . ?
C6 C7 C8 119.78(15) . . ?
C9 C8 C7 120.54(15) . . ?
C8 C9 C4 120.36(15) . . ?
N1 C11 C12 103.44(14) . . ?
C13 C12 C11 105.16(14) . . ?
C12 C13 C14 104.24(15) . . ?
N1 C14 C13 103.09(13) . . ?

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
C3 N3 N4 C4 -177.15(12) . . . . ?
C2 N2 C1 N1 -179.33(15) . . . . ?
C2 N2 C1 S1 0.32(18) . . . . ?
C14 N1 C1 N2 179.02(15) . . . . ?
C11 N1 C1 N2 4.3(2) . . . . ?
C14 N1 C1 S1 -0.6(2) . . . . ?
C11 N1 C1 S1 -175.36(12) . . . . ?
C3 S1 C1 N2 -0.05(13) . . . . ?
C3 S1 C1 N1 179.61(13) . . . . ?
C1 N2 C2 C3 -0.5(2) . . . . ?
N4 N3 C3 C2 179.28(15) . . . . ?
N4 N3 C3 S1 1.9(2) . . . . ?
N2 C2 C3 N3 -177.20(14) . . . . ?
N2 C2 C3 S1 0.5(2) . . . . ?
C1 S1 C3 N3 177.47(14) . . . . ?
C1 S1 C3 C2 -0.23(13) . . . . ?
N3 N4 C4 C5 -176.18(13) . . . . ?
N3 N4 C4 C9 5.4(2) . . . . ?
C9 C4 C5 C6 0.6(2) . . . . ?
N4 C4 C5 C6 -177.88(14) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C10 O1 C7 C6 -5.9(3) . . . . ?
C10 O1 C7 C8 174.60(17) . . . . ?
C5 C6 C7 O1 179.56(16) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
O1 C7 C8 C9 -179.66(15) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C7 C8 C9 C4 0.1(2) . . . . ?
C5 C4 C9 C8 -0.8(2) . . . . ?
N4 C4 C9 C8 177.59(15) . . . . ?
C1 N1 C11 C12 -177.89(14) . . . . ?
C14 N1 C11 C12 6.81(19) . . . . ?
N1 C11 C12 C13 -25.05(19) . . . . ?
C11 C12 C13 C14 34.00(19) . . . . ?
C1 N1 C14 C13 -161.24(15) . . . . ?
C11 N1 C14 C13 13.95(18) . . . . ?
C12 C13 C14 N1 -28.97(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.263
_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_azo-nitro
_database_code_depnum_ccdc_archive 'CCDC 1478446'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2016-06-24 downloaded from the CCDC.
;
_audit_creation_date             06/30/2014
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'compound 3a'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 N5 O2 S'
_chemical_formula_weight         303.34

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   P21/n

loop_
_symmetry_equiv_pos_as_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                   6.0819(3)
_cell_length_b                   32.2686(17)
_cell_length_c                   7.3498(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.852(2)
_cell_angle_gamma                90.00
_cell_volume                     1356.71(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    88
_cell_measurement_theta_min      5.5
_cell_measurement_theta_max      28.5

_exptl_crystal_description       plates
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8826
_exptl_absorpt_correction_T_max  0.9504
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phin and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23550
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         28.68
_reflns_number_total             3215
_reflns_number_gt                2871
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0719P)²+0.5706P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.03015(7) 0.091658(12) 0.36295(6) 0.03641(15) Uani 1 1 d . . .
C1 C 0.2712(3) 0.12497(5) 0.4339(2) 0.0354(3) Uani 1 1 d . . .
C2 C 0.4437(3) 0.06848(5) 0.3883(3) 0.0407(4) Uani 1 1 d . . .
H2 H 0.5674 0.0520 0.3843 0.049 Uiso 1 1 calc R . .
C3 C 0.2211(3) 0.05283(5) 0.3415(2) 0.0357(3) Uani 1 1 d . . .
C4 C -0.1223(3) -0.03550(5) 0.1914(2) 0.0331(3) Uani 1 1 d . . .
C5 C 0.0372(3) -0.06580(5) 0.1820(3) 0.0386(4) Uani 1 1 d . . .
H5 H 0.1949 -0.0592 0.2162 0.046 Uiso 1 1 calc R . .
C6 C -0.0374(3) -0.10550(6) 0.1223(3) 0.0402(4) Uani 1 1 d . . .
H6 H 0.0683 -0.1258 0.1163 0.048 Uiso 1 1 calc R . .
C7 C -0.2738(3) -0.11439(5) 0.0717(2) 0.0369(3) Uani 1 1 d . . .
C8 C -0.4350(3) -0.08497(6) 0.0800(3) 0.0419(4) Uani 1 1 d . . .
H8 H -0.5925 -0.0917 0.0452 0.050 Uiso 1 1 calc R . .
C9 C -0.3589(3) -0.04544(5) 0.1407(3) 0.0395(4) Uani 1 1 d . . .
H9 H -0.4653 -0.0254 0.1478 0.047 Uiso 1 1 calc R . .
C10 C 0.4337(3) 0.19515(6) 0.5159(3) 0.0497(4) Uani 1 1 d . . .
H10A H 0.5176 0.1922 0.4256 0.060 Uiso 1 1 calc R . .
H10B H 0.5432 0.1929 0.6469 0.060 Uiso 1 1 calc R . .
C11 C 0.3008(4) 0.23587(6) 0.4857(4) 0.0622(6) Uani 1 1 d . . .
H11A H 0.2566 0.2449 0.3522 0.075 Uiso 1 1 calc R . .
H11B H 0.3942 0.2574 0.5688 0.075 Uiso 1 1 calc R . .
C12 C 0.0203(3) 0.18254(6) 0.4624(3) 0.0489(4) Uani 1 1 d . . .
H12A H -0.0541 0.1675 0.5400 0.059 Uiso 1 1 calc R . .
H12B H -0.0839 0.1830 0.3290 0.059 Uiso 1 1 calc R . .
N1 N 0.1569(3) 0.01346(4) 0.2867(2) 0.0371(3) Uani 1 1 d . . .
N2 N -0.0609(2) 0.00596(4) 0.2488(2) 0.0364(3) Uani 1 1 d . . .
N3 N -0.3549(3) -0.15619(5) 0.0073(2) 0.0484(4) Uani 1 1 d . . .
N4 N 0.2451(3) 0.16420(5) 0.4784(2) 0.0427(3) Uani 1 1 d . . .
O1 O -0.2154(3) -0.18085(5) -0.0192(3) 0.0731(5) Uani 1 1 d . . .
O2 O -0.5584(3) -0.16508(5) -0.0169(3) 0.0719(5) Uani 1 1 d . . .
N5 N 0.4753(3) 0.10891(5) 0.4405(2) 0.0421(3) Uani 1 1 d . . .
C13 C 0.0861(4) 0.22603(7) 0.5393(4) 0.0634(6) Uani 1 1 d . . .
H13A H 0.1224 0.2270 0.6783 0.076 Uiso 1 1 calc R . .
H13B H -0.0394 0.2454 0.4787 0.076 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 C1 1.7484(17) . ?
S1 C3 1.7515(17) . ?
C1 N4 1.330(2) . ?
C1 N5 1.331(2) . ?
C2 N5 1.355(2) . ?
C2 C3 1.374(2) . ?
C3 N1 1.350(2) . ?
C4 C5 1.395(2) . ?
C4 C9 1.396(2) . ?
C4 N2 1.414(2) . ?
C5 C6 1.380(2) . ?
C6 C7 1.387(2) . ?
C7 C8 1.381(2) . ?
C7 N3 1.459(2) . ?
C8 C9 1.379(2) . ?
C10 N4 1.475(2) . ?
C10 C11 1.519(3) . ?
C11 C13 1.519(4) . ?
C12 N4 1.457(2) . ?
C12 C13 1.515(3) . ?
N1 N2 1.281(2) . ?
N3 O2 1.223(2) . ?
N3 O1 1.226(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
C1 S1 C3 87.26(8) . . ?
N4 C1 N5 123.32(15) . . ?
N4 C1 S1 120.03(13) . . ?
N5 C1 S1 116.65(12) . . ?
N5 C2 C3 117.23(15) . . ?
N1 C3 C2 125.52(15) . . ?
N1 C3 S1 124.52(13) . . ?
C2 C3 S1 109.97(12) . . ?
C5 C4 C9 119.77(15) . . ?
C5 C4 N2 124.06(15) . . ?
C9 C4 N2 116.17(14) . . ?
C6 C5 C4 120.50(16) . . ?
C5 C6 C7 118.43(16) . . ?
C8 C7 C6 122.19(16) . . ?
C8 C7 N3 118.87(16) . . ?
C6 C7 N3 118.94(16) . . ?
C9 C8 C7 119.01(16) . . ?
C8 C9 C4 120.10(16) . . ?
N4 C10 C11 102.54(16) . . ?
C10 C11 C13 104.06(18) . . ?
N4 C12 C13 102.96(16) . . ?
N2 N1 C3 114.57(14) . . ?
N1 N2 C4 113.12(14) . . ?
O2 N3 O1 123.04(18) . . ?
O2 N3 C7 118.56(17) . . ?
O1 N3 C7 118.40(17) . . ?
C1 N4 C12 123.61(15) . . ?
C1 N4 C10 122.71(15) . . ?
C12 N4 C10 112.88(15) . . ?
C1 N5 C2 108.89(14) . . ?
C12 C13 C11 103.79(18) . . ?

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
C3 S1 C1 N4 -179.61(15) . . . . ?
C3 S1 C1 N5 0.29(14) . . . . ?
N5 C2 C3 N1 -179.92(16) . . . . ?
N5 C2 C3 S1 0.2(2) . . . . ?
C1 S1 C3 N1 179.85(15) . . . . ?
C1 S1 C3 C2 -0.23(13) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
N2 C4 C5 C6 -179.26(15) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C5 C6 C7 N3 179.65(15) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
N3 C7 C8 C9 -179.97(16) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C5 C4 C9 C8 -0.5(3) . . . . ?
N2 C4 C9 C8 178.97(15) . . . . ?
N4 C10 C11 C13 29.0(2) . . . . ?
C2 C3 N1 N2 -179.52(16) . . . . ?
S1 C3 N1 N2 0.4(2) . . . . ?
C3 N1 N2 C4 179.85(13) . . . . ?
C5 C4 N2 N1 1.8(2) . . . . ?
C9 C4 N2 N1 -177.64(14) . . . . ?
C8 C7 N3 O2 -7.9(3) . . . . ?
C6 C7 N3 O2 172.12(18) . . . . ?
C8 C7 N3 O1 172.45(18) . . . . ?
C6 C7 N3 O1 -7.5(3) . . . . ?
N5 C1 N4 C12 176.83(17) . . . . ?
S1 C1 N4 C12 -3.3(3) . . . . ?
N5 C1 N4 C10 7.8(3) . . . . ?
S1 C1 N4 C10 -172.27(14) . . . . ?
C13 C12 N4 C1 176.96(18) . . . . ?
C13 C12 N4 C10 -13.1(2) . . . . ?
C11 C10 N4 C1 160.02(19) . . . . ?
C11 C10 N4 C12 -10.0(2) . . . . ?
N4 C1 N5 C2 179.65(17) . . . . ?
S1 C1 N5 C2 -0.2(2) . . . . ?
C3 C2 N5 C1 0.0(2) . . . . ?
N4 C12 C13 C11 30.8(2) . . . . ?
C10 C11 C13 C12 -37.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.920
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.096
