# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_13b
_database_code_depnum_ccdc_archive 'CCDC 1423524'
_audit_update_record             
;
2015-09-10 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;

_audit_creation_date             2015-09-10T10:50:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C9 H11 N5 S'
_chemical_formula_moiety         'C9 H11 N5 S'
_chemical_formula_weight         221.29
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
_space_group_IT_number           29
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   21.0057(3)
_cell_length_b                   4.06460(10)
_cell_length_c                   12.0663(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1030.22(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200.00(10)
_cell_measurement_reflns_used    8618
_cell_measurement_theta_min      4.1770
_cell_measurement_theta_max      73.4440

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             464

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.582
_exptl_absorpt_correction_T_min  0.79540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics, implemented in 
SCALE3 ABSPACK scaling algorithm.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      200.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_number            13406
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.209
_diffrn_reflns_theta_max         73.611
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_coverage         0.899
_reflns_number_total             2040
_reflns_number_gt                1980
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.1641P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2040
_refine_ls_number_parameters     144
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(8)
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.033

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50793(2) 0.15728(16) 0.53023(6) 0.04479(19) Uani 1 1 d . . . . .
N3 N 0.71012(9) 0.7618(5) 0.45329(14) 0.0290(4) Uani 1 1 d . . . . .
C5 C 0.65802(11) 0.5920(6) 0.41027(17) 0.0291(5) Uani 1 1 d . . . . .
N2 N 0.61653(9) 0.4703(5) 0.48309(15) 0.0314(4) Uani 1 1 d . . . . .
C9 C 0.79565(10) 1.0508(6) 0.44665(19) 0.0320(5) Uani 1 1 d . . . . .
N4 N 0.75481(9) 0.8973(5) 0.38070(15) 0.0316(4) Uani 1 1 d . . . . .
C2 C 0.56588(11) 0.3195(6) 0.4404(2) 0.0353(5) Uani 1 1 d . . . . .
N1 N 0.55206(10) 0.2769(6) 0.33323(18) 0.0435(5) Uani 1 1 d . . . . .
H1N H 0.7069(18) 0.766(8) 0.708(3) 0.065 Uiso 1 1 d . U . . .
H2N H 0.6571(19) 0.590(9) 0.641(3) 0.065 Uiso 1 1 d . U . . .
C4 C 0.64999(11) 0.5572(7) 0.29599(18) 0.0377(5) Uani 1 1 d . . . . .
H4 H 0.6795 0.6372 0.2453 0.045 Uiso 1 1 calc R U . . .
C3 C 0.59556(13) 0.3973(8) 0.2635(2) 0.0437(6) Uani 1 1 d . . . . .
H3 H 0.5885 0.371 0.1879 0.052 Uiso 1 1 calc R U . . .
C10 C 0.85302(12) 1.2184(7) 0.3996(2) 0.0418(6) Uani 1 1 d . . . . .
H10A H 0.889 1.0739 0.4043 0.063 Uiso 1 1 calc R U . . .
H10B H 0.8615 1.4156 0.4408 0.063 Uiso 1 1 calc R U . . .
H10C H 0.8453 1.2734 0.3234 0.063 Uiso 1 1 calc R U . . .
N5 N 0.68861(10) 0.7426(7) 0.64959(16) 0.0400(5) Uani 1 1 d . . . . .
C7 C 0.72461(10) 0.8363(6) 0.56230(16) 0.0306(5) Uani 1 1 d . . . . .
C8 C 0.77946(10) 1.0224(6) 0.55910(18) 0.0335(5) Uani 1 1 d . . . . .
H8 H 0.8013 1.111 0.6192 0.04 Uiso 1 1 calc R U . . .
C1 C 0.54321(12) 0.2298(8) 0.6631(2) 0.0446(6) Uani 1 1 d . . . . .
H1A H 0.585 0.1345 0.665 0.067 Uiso 1 1 calc R U . . .
H1B H 0.5173 0.1313 0.7197 0.067 Uiso 1 1 calc R U . . .
H1C H 0.5462 0.4624 0.6759 0.067 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.759(3) . ?
S1 C1 1.791(3) . ?
N3 C7 1.384(3) . ?
N3 C5 1.394(3) . ?
N3 N4 1.397(3) . ?
C5 N2 1.333(3) . ?
C5 C4 1.396(3) . ?
N2 C2 1.332(3) . ?
C9 N4 1.326(3) . ?
C9 C8 1.404(3) . ?
C9 C10 1.496(3) . ?
C2 N1 1.336(3) . ?
N1 C3 1.335(4) . ?
C4 C3 1.373(4) . ?
C4 H4 0.93 . ?
C3 H3 0.93 . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?
N5 C7 1.351(3) . ?
N5 H1N 0.81(4) . ?
N5 H2N 0.91(4) . ?
C7 C8 1.379(3) . ?
C8 H8 0.93 . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?

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
C2 S1 C1 101.77(12) . . ?
C7 N3 C5 129.42(19) . . ?
C7 N3 N4 111.21(17) . . ?
C5 N3 N4 119.29(17) . . ?
N2 C5 N3 116.85(18) . . ?
N2 C5 C4 122.3(2) . . ?
N3 C5 C4 120.8(2) . . ?
C2 N2 C5 116.0(2) . . ?
N4 C9 C8 112.6(2) . . ?
N4 C9 C10 120.5(2) . . ?
C8 C9 C10 126.8(2) . . ?
C9 N4 N3 104.12(17) . . ?
N2 C2 N1 127.4(2) . . ?
N2 C2 S1 119.13(19) . . ?
N1 C2 S1 113.43(19) . . ?
C3 N1 C2 114.4(2) . . ?
C3 C4 C5 115.5(2) . . ?
C3 C4 H4 122.2 . . ?
C5 C4 H4 122.2 . . ?
N1 C3 C4 124.3(2) . . ?
N1 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 N5 H1N 112(3) . . ?
C7 N5 H2N 121(2) . . ?
H1N N5 H2N 121(3) . . ?
N5 C7 C8 130.1(2) . . ?
N5 C7 N3 123.8(2) . . ?
C8 C7 N3 106.10(18) . . ?
C7 C8 C9 105.95(19) . . ?
C7 C8 H8 127 . . ?
C9 C8 H8 127 . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


####################################################################### 
# 
# 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_13c
_database_code_depnum_ccdc_archive 'CCDC 1423525'
_audit_update_record             
;
2015-09-10 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;

_audit_creation_date             2015-09-10T11:52:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C9 H11 N5 S'
_chemical_formula_moiety         'C9 H11 N5 S'
_chemical_formula_weight         221.29

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.54390(10)
_cell_length_b                   23.3450(4)
_cell_length_c                   5.85840(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.946(2)
_cell_angle_gamma                90
_cell_volume                     1024.16(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    7975
_cell_measurement_theta_min      3.7700
_cell_measurement_theta_max      73.0820

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             464

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.598
_exptl_absorpt_correction_T_min  0.67926
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics, implemented in 
SCALE3 ABSPACK scaling algorithm.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.016
_diffrn_reflns_number            14217
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.787
_diffrn_reflns_theta_max         66.565
_diffrn_reflns_theta_full        66.565
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             1797
_reflns_number_gt                1665
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.3255P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1797
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44312(5) 0.42785(2) 1.25476(7) 0.03497(16) Uani 1 1 d . . . . .
C9 C 0.9534(2) 0.43465(7) 0.8388(3) 0.0374(4) Uani 1 1 d . . . . .
H9A H 1.0664 0.4527 0.8276 0.056 Uiso 1 1 calc R U . . .
H9B H 0.9534 0.4185 0.9895 0.056 Uiso 1 1 calc R U . . .
H9C H 0.8598 0.4626 0.8124 0.056 Uiso 1 1 calc R U . . .
C3 C 0.3579(2) 0.30542(6) 0.8177(3) 0.0323(4) Uani 1 1 d . . . . .
H3 H 0.2682 0.2786 0.7795 0.039 Uiso 1 1 calc R U . . .
C4 C 0.5021(2) 0.30527(7) 0.6955(3) 0.0322(4) Uani 1 1 d . . . . .
H4 H 0.5132 0.2787 0.5798 0.039 Uiso 1 1 calc R U . . .
N3 N 0.78049(16) 0.35087(5) 0.6388(2) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.61668(16) 0.38511(5) 0.9221(2) 0.0267(3) Uani 1 1 d . . . . .
N5 N 1.0025(2) 0.29726(6) 0.2007(3) 0.0358(3) Uani 1 1 d . . . . .
C2 C 0.47208(19) 0.37990(6) 1.0306(3) 0.0274(3) Uani 1 1 d . . . . .
N4 N 0.79235(17) 0.31261(5) 0.4576(2) 0.0301(3) Uani 1 1 d . . . . .
C5 C 0.63079(19) 0.34715(6) 0.7548(3) 0.0265(3) Uani 1 1 d . . . . .
N1 N 0.33926(17) 0.34219(5) 0.9893(2) 0.0307(3) Uani 1 1 d . . . . .
C8 C 0.9232(2) 0.38841(6) 0.6634(3) 0.0289(3) Uani 1 1 d . . . . .
C7 C 1.0264(2) 0.37415(6) 0.4975(3) 0.0307(3) Uani 1 1 d . . . . .
H7 H 1.1325 0.3916 0.4697 0.037 Uiso 1 1 calc R U . . .
C6 C 0.9410(2) 0.32739(6) 0.3752(3) 0.0285(3) Uani 1 1 d . . . . .
C1 C 0.6411(2) 0.47116(8) 1.2663(3) 0.0393(4) Uani 1 1 d . . . . .
H1A H 0.7447 0.447 1.2892 0.059 Uiso 1 1 calc R U . . .
H1B H 0.6437 0.4978 1.3914 0.059 Uiso 1 1 calc R U . . .
H1C H 0.6407 0.4918 1.1244 0.059 Uiso 1 1 calc R U . . .
H2N H 1.079(3) 0.3129(8) 0.136(3) 0.035(5) Uiso 1 1 d . . . . .
H1N H 0.927(3) 0.2734(9) 0.115(3) 0.042(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.7593(15) . ?
S1 C1 1.7982(17) . ?
C9 C8 1.489(2) . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C3 N1 1.342(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.93 . ?
C4 C5 1.392(2) . ?
C4 H4 0.93 . ?
N3 C8 1.3819(19) . ?
N3 C5 1.3895(19) . ?
N3 N4 1.3982(17) . ?
N2 C5 1.3348(19) . ?
N2 C2 1.3329(19) . ?
N5 C6 1.368(2) . ?
N5 H2N 0.82(2) . ?
N5 H1N 0.90(2) . ?
C2 N1 1.334(2) . ?
N4 C6 1.319(2) . ?
C8 C7 1.358(2) . ?
C7 C6 1.418(2) . ?
C7 H7 0.93 . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?

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
C2 S1 C1 102.02(8) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C3 C4 123.63(14) . . ?
N1 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
C3 C4 C5 116.16(14) . . ?
C3 C4 H4 121.9 . . ?
C5 C4 H4 121.9 . . ?
C8 N3 C5 131.12(13) . . ?
C8 N3 N4 111.32(12) . . ?
C5 N3 N4 117.50(12) . . ?
C5 N2 C2 115.60(13) . . ?
C6 N5 H2N 116.3(13) . . ?
C6 N5 H1N 118.9(13) . . ?
H2N N5 H1N 116.9(19) . . ?
N1 C2 N2 127.89(14) . . ?
N1 C2 S1 113.38(11) . . ?
N2 C2 S1 118.73(11) . . ?
C6 N4 N3 104.25(12) . . ?
N2 C5 N3 117.34(13) . . ?
N2 C5 C4 122.30(14) . . ?
N3 C5 C4 120.36(13) . . ?
C2 N1 C3 114.41(13) . . ?
C7 C8 N3 106.08(13) . . ?
C7 C8 C9 128.20(14) . . ?
N3 C8 C9 125.72(13) . . ?
C8 C7 C6 106.58(13) . . ?
C8 C7 H7 126.7 . . ?
C6 C7 H7 126.7 . . ?
N4 C6 N5 121.31(15) . . ?
N4 C6 C7 111.77(13) . . ?
N5 C6 C7 126.82(14) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


