# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1436500'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N6 O3 S'
_chemical_formula_sum            'C20 H26 N6 O3 S'
_chemical_formula_weight         430.53

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'
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'
H H 0.0000 0.0000 '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/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   12.7147(16)
_cell_length_b                   6.2855(9)
_cell_length_c                   27.243(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.679(9)
_cell_angle_gamma                90.00
_cell_volume                     2139.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1473
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      18.18

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   multi-scan

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28786
_diffrn_reflns_av_R_equivalents  0.1946
_diffrn_reflns_av_sigmaI/netI    0.1481
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3862
_reflns_number_gt                1513
_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)+(0.0000P)²+0.0080P] 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         3862
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_restrained_S_all      0.817
_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
N5 N 0.6499(2) 0.5439(5) 0.04644(9) 0.0506(7) Uani 1 1 d . . .
S1 S 0.66271(8) 0.44219(16) 0.21111(3) 0.0756(3) Uani 1 1 d . . .
O2 O 1.0146(2) -0.5543(4) 0.14431(12) 0.1156(11) Uani 1 1 d . . .
O3 O 1.0357(2) -0.5843(4) 0.06877(11) 0.0945(9) Uani 1 1 d . . .
N4 N 0.9981(2) -0.4936(5) 0.10141(14) 0.0695(9) Uani 1 1 d . . .
N3 N 0.7555(2) 0.2456(4) 0.04708(11) 0.0522(7) Uani 1 1 d . . .
N2 N 0.7101(2) 0.3605(4) 0.12185(9) 0.0531(7) Uani 1 1 d . . .
N1 N 0.6004(2) 0.6659(4) 0.13266(9) 0.0644(8) Uani 1 1 d . . .
C12 C 0.6409(2) 0.5831(4) -0.00684(10) 0.0492(8) Uani 1 1 d . . .
H12A H 0.6023 0.4676 -0.0258 0.059 Uiso 1 1 calc R . .
H12B H 0.7115 0.5922 -0.0154 0.059 Uiso 1 1 calc R . .
C11 C 0.8219(3) -0.0290(5) 0.11114(11) 0.0543(9) Uani 1 1 d . . .
H11 H 0.7859 0.0322 0.1344 0.065 Uiso 1 1 calc R . .
C10 C 0.8827(3) -0.2118(5) 0.12310(12) 0.0611(10) Uani 1 1 d . . .
H10 H 0.8883 -0.2728 0.1546 0.073 Uiso 1 1 calc R . .
C9 C 0.9341(3) -0.3018(5) 0.08838(12) 0.0500(9) Uani 1 1 d . . .
C8 C 0.9274(2) -0.2180(5) 0.04159(12) 0.0579(9) Uani 1 1 d . . .
H8 H 0.9608 -0.2843 0.0181 0.069 Uiso 1 1 calc R . .
C7 C 0.8697(3) -0.0321(5) 0.03011(11) 0.0545(9) Uani 1 1 d . . .
H7 H 0.8672 0.0312 -0.0009 0.065 Uiso 1 1 calc R . .
C6 C 0.8155(2) 0.0613(5) 0.06434(11) 0.0477(8) Uani 1 1 d . . .
C5 C 0.7037(2) 0.3869(5) 0.07321(13) 0.0482(9) Uani 1 1 d . . .
C4 C 0.6576(3) 0.4969(5) 0.14805(11) 0.0496(9) Uani 1 1 d . . .
C3 C 0.5606(3) 0.7549(6) 0.17232(13) 0.0725(11) Uani 1 1 d . . .
H3 H 0.5181 0.8763 0.1679 0.087 Uiso 1 1 calc R . .
C2 C 0.5850(3) 0.6617(5) 0.21626(12) 0.0614(10) Uani 1 1 d . . .
C1 C 0.5509(3) 0.7238(6) 0.26450(11) 0.0920(13) Uani 1 1 d . . .
H1A H 0.5074 0.8495 0.2592 0.138 Uiso 1 1 calc R . .
H1B H 0.6132 0.7517 0.2895 0.138 Uiso 1 1 calc R . .
H1C H 0.5106 0.6099 0.2754 0.138 Uiso 1 1 calc R . .
C14 C 0.5578(2) 0.8439(5) -0.07447(10) 0.0550(9) Uani 1 1 d . . .
H14A H 0.5101 0.7364 -0.0917 0.066 Uiso 1 1 calc R . .
H14B H 0.5205 0.9792 -0.0790 0.066 Uiso 1 1 calc R . .
C13 C 0.5810(2) 0.7915(4) -0.01921(10) 0.0484(8) Uani 1 1 d . . .
H13A H 0.5138 0.7844 -0.0073 0.058 Uiso 1 1 calc R . .
H13B H 0.6229 0.9060 -0.0014 0.058 Uiso 1 1 calc R . .
N6 N 0.6531(2) 0.8566(4) -0.09805(8) 0.0495(7) Uani 1 1 d . . .
C20 C 0.7125(3) 1.0341(5) -0.09048(11) 0.0481(8) Uani 1 1 d . . .
C16 C 0.6556(3) 0.7326(5) -0.18519(12) 0.0731(11) Uani 1 1 d . . .
H16A H 0.6486 0.6007 -0.2040 0.088 Uiso 1 1 calc R . .
H16B H 0.5882 0.8083 -0.1936 0.088 Uiso 1 1 calc R . .
C15 C 0.6763(3) 0.6804(5) -0.12979(11) 0.0603(10) Uani 1 1 d . . .
H15A H 0.6328 0.5589 -0.1244 0.072 Uiso 1 1 calc R . .
H15B H 0.7508 0.6398 -0.1196 0.072 Uiso 1 1 calc R . .
O1 O 0.69294(18) 1.1784(3) -0.06281(7) 0.0664(7) Uani 1 1 d . . .
C19 C 0.8037(3) 1.0553(5) -0.11821(11) 0.0646(10) Uani 1 1 d . . .
H19A H 0.8502 0.9327 -0.1107 0.077 Uiso 1 1 calc R . .
H19B H 0.8450 1.1807 -0.1061 0.077 Uiso 1 1 calc R . .
C18 C 0.7692(3) 1.0728(6) -0.17439(11) 0.0734(11) Uani 1 1 d . . .
H18A H 0.7069 1.1647 -0.1815 0.088 Uiso 1 1 calc R . .
H18B H 0.8262 1.1407 -0.1879 0.088 Uiso 1 1 calc R . .
C17 C 0.7425(3) 0.8654(6) -0.20091(12) 0.0855(12) Uani 1 1 d . . .
H17A H 0.8072 0.7803 -0.1965 0.103 Uiso 1 1 calc R . .
H17B H 0.7217 0.8949 -0.2363 0.103 Uiso 1 1 calc R . .
H3A H 0.744(3) 0.277(5) 0.0129(12) 0.093(13) Uiso 1 1 d . . .
H5 H 0.623(2) 0.651(4) 0.0653(10) 0.059(10) 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
N5 C5 1.338(3) . ?
N5 C12 1.456(3) . ?
N5 H5 0.95(3) . ?
S1 C2 1.718(3) . ?
S1 C4 1.741(3) . ?
O2 N4 1.210(3) . ?
O3 N4 1.225(3) . ?
N4 C9 1.461(4) . ?
N3 C5 1.380(4) . ?
N3 C6 1.418(3) . ?
N3 H3A 0.94(3) . ?
N2 C5 1.323(3) . ?
N2 C4 1.367(4) . ?
N1 C4 1.311(3) . ?
N1 C3 1.393(4) . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C6 1.384(4) . ?
C11 C10 1.389(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.368(4) . ?
C10 H10 0.9300 . ?
C9 C8 1.367(4) . ?
C8 C7 1.385(4) . ?
C8 H8 0.9300 . ?
C7 C6 1.388(4) . ?
C7 H7 0.9300 . ?
C3 C2 1.317(4) . ?
C3 H3 0.9300 . ?
C2 C1 1.510(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C14 N6 1.474(4) . ?
C14 C13 1.516(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N6 C20 1.341(3) . ?
N6 C15 1.469(3) . ?
C20 O1 1.234(3) . ?
C20 C19 1.503(4) . ?
C16 C17 1.509(4) . ?
C16 C15 1.519(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C19 C18 1.516(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C18 C17 1.499(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 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
C5 N5 C12 127.3(3) . . ?
C5 N5 H5 115.4(16) . . ?
C12 N5 H5 116.7(16) . . ?
C2 S1 C4 90.27(16) . . ?
O2 N4 O3 122.2(3) . . ?
O2 N4 C9 118.9(3) . . ?
O3 N4 C9 118.8(3) . . ?
C5 N3 C6 129.3(3) . . ?
C5 N3 H3A 112(2) . . ?
C6 N3 H3A 118(2) . . ?
C5 N2 C4 119.9(3) . . ?
C4 N1 C3 109.7(3) . . ?
N5 C12 C13 108.1(2) . . ?
N5 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
N5 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C6 C11 C10 119.4(3) . . ?
C6 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C8 C9 C10 122.0(3) . . ?
C8 C9 N4 118.7(3) . . ?
C10 C9 N4 119.3(3) . . ?
C9 C8 C7 118.3(3) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C11 C6 C7 119.6(3) . . ?
C11 C6 N3 125.2(3) . . ?
C7 C6 N3 115.2(3) . . ?
N2 C5 N5 124.7(3) . . ?
N2 C5 N3 119.3(3) . . ?
N5 C5 N3 116.0(3) . . ?
N1 C4 N2 129.6(3) . . ?
N1 C4 S1 113.1(2) . . ?
N2 C4 S1 117.3(2) . . ?
C2 C3 N1 117.9(3) . . ?
C2 C3 H3 121.0 . . ?
N1 C3 H3 121.0 . . ?
C3 C2 C1 128.2(3) . . ?
C3 C2 S1 109.0(3) . . ?
C1 C2 S1 122.8(3) . . ?
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 . . ?
N6 C14 C13 114.9(2) . . ?
N6 C14 H14A 108.5 . . ?
C13 C14 H14A 108.5 . . ?
N6 C14 H14B 108.5 . . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C13 C12 113.9(2) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C20 N6 C15 123.3(3) . . ?
C20 N6 C14 117.6(3) . . ?
C15 N6 C14 119.1(3) . . ?
O1 C20 N6 122.3(3) . . ?
O1 C20 C19 120.2(3) . . ?
N6 C20 C19 117.5(3) . . ?
C17 C16 C15 113.6(3) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
N6 C15 C16 113.9(2) . . ?
N6 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
N6 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C20 C19 C18 114.1(3) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C17 C18 C19 114.9(3) . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18B 108.5 . . ?
C19 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C18 C17 C16 117.2(3) . . ?
C18 C17 H17A 108.0 . . ?
C16 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
C16 C17 H17B 108.0 . . ?
H17A C17 H17B 107.2 . . ?

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
C5 N5 C12 C13 -174.5(3) . . . . ?
C6 C11 C10 C9 -0.8(5) . . . . ?
C11 C10 C9 C8 -0.3(5) . . . . ?
C11 C10 C9 N4 179.8(3) . . . . ?
O2 N4 C9 C8 171.4(3) . . . . ?
O3 N4 C9 C8 -6.6(5) . . . . ?
O2 N4 C9 C10 -8.7(5) . . . . ?
O3 N4 C9 C10 173.3(3) . . . . ?
C10 C9 C8 C7 2.3(5) . . . . ?
N4 C9 C8 C7 -177.8(3) . . . . ?
C9 C8 C7 C6 -3.2(5) . . . . ?
C10 C11 C6 C7 0.0(4) . . . . ?
C10 C11 C6 N3 179.2(3) . . . . ?
C8 C7 C6 C11 2.0(4) . . . . ?
C8 C7 C6 N3 -177.2(3) . . . . ?
C5 N3 C6 C11 8.9(5) . . . . ?
C5 N3 C6 C7 -171.8(3) . . . . ?
C4 N2 C5 N5 1.5(5) . . . . ?
C4 N2 C5 N3 -178.8(3) . . . . ?
C12 N5 C5 N2 179.1(3) . . . . ?
C12 N5 C5 N3 -0.6(4) . . . . ?
C6 N3 C5 N2 2.5(5) . . . . ?
C6 N3 C5 N5 -177.8(3) . . . . ?
C3 N1 C4 N2 179.2(3) . . . . ?
C3 N1 C4 S1 0.5(3) . . . . ?
C5 N2 C4 N1 -2.7(5) . . . . ?
C5 N2 C4 S1 176.0(2) . . . . ?
C2 S1 C4 N1 -0.8(3) . . . . ?
C2 S1 C4 N2 -179.6(3) . . . . ?
C4 N1 C3 C2 0.1(5) . . . . ?
N1 C3 C2 C1 -178.9(3) . . . . ?
N1 C3 C2 S1 -0.7(4) . . . . ?
C4 S1 C2 C3 0.8(3) . . . . ?
C4 S1 C2 C1 179.2(3) . . . . ?
N6 C14 C13 C12 -57.6(3) . . . . ?
N5 C12 C13 C14 -175.4(2) . . . . ?
C13 C14 N6 C20 -78.0(3) . . . . ?
C13 C14 N6 C15 104.1(3) . . . . ?
C15 N6 C20 O1 -178.4(3) . . . . ?
C14 N6 C20 O1 3.8(4) . . . . ?
C15 N6 C20 C19 3.2(4) . . . . ?
C14 N6 C20 C19 -174.6(2) . . . . ?
C20 N6 C15 C16 -70.1(4) . . . . ?
C14 N6 C15 C16 107.7(3) . . . . ?
C17 C16 C15 N6 78.0(4) . . . . ?
O1 C20 C19 C18 -112.7(3) . . . . ?
N6 C20 C19 C18 65.7(4) . . . . ?
C20 C19 C18 C17 -80.7(4) . . . . ?
C19 C18 C17 C16 57.9(4) . . . . ?
C15 C16 C17 C18 -56.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1436501'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N4 O2 S2, C4 H9 N O'
_chemical_formula_sum            'C15 H19 N5 O3 S2'
_chemical_formula_weight         381.47

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5882(6)
_cell_length_b                   9.0566(7)
_cell_length_c                   13.2569(9)
_cell_angle_alpha                93.909(4)
_cell_angle_beta                 107.379(4)
_cell_angle_gamma                107.982(4)
_cell_volume                     921.26(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4193
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.59

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   multi-scan

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12000
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3152
_reflns_number_gt                2348
_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)+(0.0000P)²+0.6000P] 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         3152
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
S2 S 0.15430(9) 0.74647(7) 0.02646(5) 0.0542(2) Uani 1 1 d . . .
S1 S 0.26176(8) 1.09627(7) 0.08753(5) 0.05046(19) Uani 1 1 d . . .
O1 O -0.3987(3) 0.2900(3) 0.45659(19) 0.1084(9) Uani 1 1 d . . .
O2 O -0.2711(4) 0.5235(3) 0.55005(19) 0.1088(9) Uani 1 1 d . . .
N1 N 0.1396(3) 1.1434(2) 0.23286(16) 0.0478(5) Uani 1 1 d . . .
N2 N 0.0748(2) 0.8762(2) 0.18694(14) 0.0445(5) Uani 1 1 d . . .
N3 N -0.0046(2) 0.6068(2) 0.15402(15) 0.0494(5) Uani 1 1 d . . .
H3A H -0.0116 0.5260 0.1125 0.059 Uiso 1 1 calc R . .
N4 N -0.3029(3) 0.4269(3) 0.4714(2) 0.0730(7) Uani 1 1 d . . .
C1 C 0.3839(4) 1.4256(3) 0.0938(2) 0.0739(9) Uani 1 1 d . . .
H1A H 0.3580 1.5171 0.1133 0.111 Uiso 1 1 calc R . .
H1B H 0.3444 1.3977 0.0170 0.111 Uiso 1 1 calc R . .
H1C H 0.5072 1.4483 0.1221 0.111 Uiso 1 1 calc R . .
C2 C 0.2929(3) 1.2902(3) 0.1395(2) 0.0511(6) Uani 1 1 d . . .
C3 C 0.2195(3) 1.2914(3) 0.21481(19) 0.0517(6) Uani 1 1 d . . .
H3 H 0.2219 1.3835 0.2518 0.062 Uiso 1 1 calc R . .
C4 C 0.1483(3) 1.0230(3) 0.17314(17) 0.0421(6) Uani 1 1 d . . .
C5 C 0.0733(3) 0.7499(3) 0.12848(17) 0.0424(6) Uani 1 1 d . . .
C6 C -0.0746(3) 0.5703(3) 0.23640(18) 0.0436(6) Uani 1 1 d . . .
C11 C -0.0438(4) 0.6774(3) 0.32612(19) 0.0594(7) Uani 1 1 d . . .
H11 H 0.0261 0.7819 0.3341 0.071 Uiso 1 1 calc R . .
C10 C -0.1162(4) 0.6298(3) 0.4036(2) 0.0625(8) Uani 1 1 d . . .
H10 H -0.0930 0.7014 0.4645 0.075 Uiso 1 1 calc R . .
C9 C -0.2224(3) 0.4767(3) 0.39045(19) 0.0513(6) Uani 1 1 d . . .
C8 C -0.2536(4) 0.3676(3) 0.3032(2) 0.0606(7) Uani 1 1 d . . .
H8 H -0.3244 0.2635 0.2958 0.073 Uiso 1 1 calc R . .
C7 C -0.1788(3) 0.4145(3) 0.2269(2) 0.0565(7) Uani 1 1 d . . .
H7 H -0.1982 0.3408 0.1680 0.068 Uiso 1 1 calc R . .
O3 O 0.9128(2) 1.0688(2) 0.34718(13) 0.0608(5) Uani 1 1 d . . .
N5 N 0.6601(3) 0.9178(3) 0.35898(16) 0.0594(6) Uani 1 1 d . . .
C14 C 0.7603(3) 0.9772(3) 0.3018(2) 0.0536(7) Uani 1 1 d . . .
C13 C 0.7294(4) 0.9607(4) 0.47639(19) 0.0701(9) Uani 1 1 d . . .
H13A H 0.8537 0.9902 0.5005 0.105 Uiso 1 1 calc R . .
H13B H 0.6813 0.8721 0.5072 0.105 Uiso 1 1 calc R . .
H13C H 0.6986 1.0478 0.4984 0.105 Uiso 1 1 calc R . .
C12 C 0.4798(4) 0.8107(5) 0.3131(2) 0.1091(14) Uani 1 1 d . . .
H12A H 0.4474 0.7886 0.2364 0.164 Uiso 1 1 calc R . .
H12B H 0.4050 0.8590 0.3321 0.164 Uiso 1 1 calc R . .
H12C H 0.4686 0.7141 0.3408 0.164 Uiso 1 1 calc R . .
C15 C 0.6871(4) 0.9309(4) 0.1812(2) 0.0713(8) Uani 1 1 d . . .
H15A H 0.7680 0.9925 0.1505 0.107 Uiso 1 1 calc R . .
H15B H 0.5791 0.9496 0.1549 0.107 Uiso 1 1 calc R . .
H15C H 0.6674 0.8210 0.1614 0.107 Uiso 1 1 calc R . .
H1 H 0.074(3) 1.128(3) 0.276(2) 0.064(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
S2 C5 1.698(2) . ?
S1 C4 1.744(2) . ?
S1 C2 1.751(2) . ?
O1 N4 1.222(3) . ?
O2 N4 1.218(3) . ?
N1 C4 1.338(3) . ?
N1 C3 1.378(3) . ?
N1 H1 0.90(2) . ?
N2 C5 1.332(3) . ?
N2 C4 1.336(3) . ?
N3 C5 1.379(3) . ?
N3 C6 1.408(3) . ?
N3 H3A 0.8600 . ?
N4 C9 1.466(3) . ?
C1 C2 1.508(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.331(3) . ?
C3 H3 0.9300 . ?
C6 C11 1.387(3) . ?
C6 C7 1.391(3) . ?
C11 C10 1.381(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.370(3) . ?
C10 H10 0.9300 . ?
C9 C8 1.371(3) . ?
C8 C7 1.377(3) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
O3 C14 1.247(3) . ?
N5 C14 1.329(3) . ?
N5 C12 1.462(3) . ?
N5 C13 1.466(3) . ?
C14 C15 1.508(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C4 S1 C2 91.04(11) . . ?
C4 N1 C3 115.6(2) . . ?
C4 N1 H1 121.9(16) . . ?
C3 N1 H1 122.0(16) . . ?
C5 N2 C4 122.57(18) . . ?
C5 N3 C6 131.06(19) . . ?
C5 N3 H3A 114.5 . . ?
C6 N3 H3A 114.5 . . ?
O2 N4 O1 123.2(2) . . ?
O2 N4 C9 118.6(2) . . ?
O1 N4 C9 118.2(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 . . ?
C3 C2 C1 129.5(2) . . ?
C3 C2 S1 110.31(17) . . ?
C1 C2 S1 120.08(19) . . ?
C2 C3 N1 113.8(2) . . ?
C2 C3 H3 123.1 . . ?
N1 C3 H3 123.1 . . ?
N2 C4 N1 118.91(19) . . ?
N2 C4 S1 131.85(17) . . ?
N1 C4 S1 109.24(16) . . ?
N2 C5 N3 115.54(19) . . ?
N2 C5 S2 127.26(17) . . ?
N3 C5 S2 117.20(16) . . ?
C11 C6 C7 118.6(2) . . ?
C11 C6 N3 124.5(2) . . ?
C7 C6 N3 116.86(19) . . ?
C10 C11 C6 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 N4 119.8(2) . . ?
C8 C9 N4 119.0(2) . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C14 N5 C12 124.6(2) . . ?
C14 N5 C13 119.6(2) . . ?
C12 N5 C13 115.8(2) . . ?
O3 C14 N5 120.6(2) . . ?
O3 C14 C15 120.6(2) . . ?
N5 C14 C15 118.8(2) . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C4 S1 C2 C3 -0.4(2) . . . . ?
C4 S1 C2 C1 -177.3(2) . . . . ?
C1 C2 C3 N1 176.7(3) . . . . ?
S1 C2 C3 N1 0.2(3) . . . . ?
C4 N1 C3 C2 0.2(3) . . . . ?
C5 N2 C4 N1 177.9(2) . . . . ?
C5 N2 C4 S1 -2.1(4) . . . . ?
C3 N1 C4 N2 179.5(2) . . . . ?
C3 N1 C4 S1 -0.5(3) . . . . ?
C2 S1 C4 N2 -179.5(2) . . . . ?
C2 S1 C4 N1 0.45(19) . . . . ?
C4 N2 C5 N3 178.7(2) . . . . ?
C4 N2 C5 S2 -1.9(4) . . . . ?
C6 N3 C5 N2 -4.5(4) . . . . ?
C6 N3 C5 S2 176.1(2) . . . . ?
C5 N3 C6 C11 -15.4(4) . . . . ?
C5 N3 C6 C7 166.0(2) . . . . ?
C7 C6 C11 C10 -0.4(4) . . . . ?
N3 C6 C11 C10 -179.0(3) . . . . ?
C6 C11 C10 C9 -1.5(4) . . . . ?
C11 C10 C9 C8 2.3(4) . . . . ?
C11 C10 C9 N4 -178.5(3) . . . . ?
O2 N4 C9 C10 -1.1(4) . . . . ?
O1 N4 C9 C10 179.1(3) . . . . ?
O2 N4 C9 C8 178.1(3) . . . . ?
O1 N4 C9 C8 -1.6(4) . . . . ?
C10 C9 C8 C7 -1.1(4) . . . . ?
N4 C9 C8 C7 179.6(3) . . . . ?
C9 C8 C7 C6 -0.9(4) . . . . ?
C11 C6 C7 C8 1.6(4) . . . . ?
N3 C6 C7 C8 -179.7(2) . . . . ?
C12 N5 C14 O3 179.6(3) . . . . ?
C13 N5 C14 O3 0.1(4) . . . . ?
C12 N5 C14 C15 -0.9(4) . . . . ?
C13 N5 C14 C15 179.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1436502'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N4 O2 S2, C2 H6 O S'
_chemical_formula_sum            'C13 H16 N4 O3 S3'
_chemical_formula_weight         372.48

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8556(4)
_cell_length_b                   10.5492(5)
_cell_length_c                   11.5009(6)
_cell_angle_alpha                91.605(3)
_cell_angle_beta                 102.511(3)
_cell_angle_gamma                110.839(2)
_cell_volume                     863.80(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6485
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      28.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_process_details   multi-scan

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12850
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3058
_reflns_number_gt                2624
_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)+(0.0000P)²+0.5000P] 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         3058
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 1.33495(7) 0.83371(5) 0.85199(4) 0.04626(15) Uani 1 1 d . . .
S2 S 1.16081(8) 0.96198(5) 0.66221(5) 0.05836(18) Uani 1 1 d . . .
C6 C 0.7423(3) 0.65477(19) 0.44482(16) 0.0391(4) Uani 1 1 d . . .
C9 C 0.4644(3) 0.4356(2) 0.29634(17) 0.0417(4) Uani 1 1 d . . .
C11 C 0.7388(3) 0.5236(2) 0.45830(17) 0.0442(5) Uani 1 1 d . . .
H11 H 0.8304 0.5095 0.5169 0.053 Uiso 1 1 calc R . .
C8 C 0.4637(3) 0.5646(2) 0.28243(18) 0.0479(5) Uani 1 1 d . . .
H8 H 0.3715 0.5778 0.2237 0.057 Uiso 1 1 calc R . .
C10 C 0.5983(3) 0.4139(2) 0.38396(17) 0.0461(5) Uani 1 1 d . . .
H10 H 0.5942 0.3257 0.3931 0.055 Uiso 1 1 calc R . .
C7 C 0.6018(3) 0.6734(2) 0.35690(17) 0.0477(5) Uani 1 1 d . . .
H7 H 0.6020 0.7609 0.3488 0.057 Uiso 1 1 calc R . .
C5 C 1.0145(3) 0.79714(19) 0.61556(16) 0.0405(4) Uani 1 1 d . . .
C4 C 1.1408(3) 0.69617(19) 0.77075(16) 0.0389(4) Uani 1 1 d . . .
C2 C 1.3982(3) 0.7282(2) 0.95283(17) 0.0475(5) Uani 1 1 d . . .
C3 C 1.2740(3) 0.6005(2) 0.92416(18) 0.0507(5) Uani 1 1 d . . .
H3 H 1.2823 0.5293 0.9680 0.061 Uiso 1 1 calc R . .
C1 C 1.5713(3) 0.7863(3) 1.0531(2) 0.0660(7) Uani 1 1 d . . .
H1A H 1.5495 0.8402 1.1128 0.099 Uiso 1 1 calc R . .
H1B H 1.6739 0.8427 1.0224 0.099 Uiso 1 1 calc R . .
H1C H 1.6016 0.7132 1.0884 0.099 Uiso 1 1 calc R . .
N1 N 1.1324(3) 0.58377(18) 0.82372(15) 0.0477(4) Uani 1 1 d . . .
N2 N 1.0137(2) 0.68760(15) 0.67012(13) 0.0408(4) Uani 1 1 d . . .
N3 N 0.8796(2) 0.77490(18) 0.51085(15) 0.0460(4) Uani 1 1 d . . .
N4 N 0.3195(2) 0.32099(18) 0.21519(16) 0.0517(4) Uani 1 1 d . . .
O2 O 0.3009(2) 0.20543(16) 0.23928(16) 0.0717(5) Uani 1 1 d . . .
O1 O 0.2231(2) 0.34506(17) 0.12538(14) 0.0674(5) Uani 1 1 d . . .
O3 O 0.1253(3) 0.67446(18) 0.2324(2) 0.1130(9) Uani 1 1 d . . .
C12 C 0.2733(5) 0.9166(4) 0.3557(3) 0.0821(9) Uani 1 1 d . . .
C13 C 0.1123(5) 0.8854(3) 0.1208(3) 0.0807(9) Uani 1 1 d . . .
S3' S 0.07711(10) 0.79732(7) 0.24637(8) 0.0612(2) Uani 0.84 1 d P . .
S3 S 0.2173(9) 0.8003(6) 0.2335(5) 0.0957(16) Uani 0.16 1 d P . .
H3A H 0.879(3) 0.844(2) 0.4859(19) 0.053(7) Uiso 1 1 d . . .
H1 H 1.042(3) 0.507(2) 0.795(2) 0.063(7) Uiso 1 1 d . . .
H12A H 0.252(5) 1.008(4) 0.366(3) 0.143(14) Uiso 1 1 d . . .
H12B H 0.391(5) 0.933(3) 0.333(3) 0.105(12) Uiso 1 1 d . . .
H12C H 0.281(5) 0.880(4) 0.427(3) 0.121(13) Uiso 1 1 d . . .
H13A H 0.025(5) 0.822(4) 0.051(3) 0.124(12) Uiso 1 1 d . . .
H13B H 0.085(5) 0.967(4) 0.130(3) 0.137(14) Uiso 1 1 d . . .
H13C H 0.242(5) 0.905(4) 0.115(3) 0.130(14) 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 C4 1.7426(19) . ?
S1 C2 1.746(2) . ?
S2 C5 1.7004(19) . ?
C6 C11 1.388(3) . ?
C6 C7 1.400(3) . ?
C6 N3 1.402(2) . ?
C9 C8 1.376(3) . ?
C9 C10 1.378(3) . ?
C9 N4 1.458(2) . ?
C11 C10 1.384(3) . ?
C8 C7 1.372(3) . ?
C5 N2 1.329(2) . ?
C5 N3 1.372(2) . ?
C4 N2 1.332(2) . ?
C4 N1 1.336(2) . ?
C2 C3 1.332(3) . ?
C2 C1 1.497(3) . ?
C3 N1 1.377(2) . ?
N4 O2 1.222(2) . ?
N4 O1 1.232(2) . ?
O3 S3 1.264(6) . ?
O3 S3' 1.488(2) . ?
C12 S3 1.711(6) . ?
C12 S3' 1.798(3) . ?
C13 S3' 1.757(3) . ?
C13 S3 1.814(7) . ?
S3' S3 1.132(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
C4 S1 C2 91.36(9) . . ?
C11 C6 C7 119.22(17) . . ?
C11 C6 N3 125.48(17) . . ?
C7 C6 N3 115.28(17) . . ?
C8 C9 C10 121.44(18) . . ?
C8 C9 N4 118.31(18) . . ?
C10 C9 N4 120.25(18) . . ?
C10 C11 C6 119.55(18) . . ?
C7 C8 C9 118.69(18) . . ?
C9 C10 C11 119.96(18) . . ?
C8 C7 C6 121.12(19) . . ?
N2 C5 N3 116.25(17) . . ?
N2 C5 S2 127.39(14) . . ?
N3 C5 S2 116.35(14) . . ?
N2 C4 N1 119.55(17) . . ?
N2 C4 S1 131.47(15) . . ?
N1 C4 S1 108.95(14) . . ?
C3 C2 C1 129.8(2) . . ?
C3 C2 S1 110.05(15) . . ?
C1 C2 S1 120.12(16) . . ?
C2 C3 N1 113.85(19) . . ?
C4 N1 C3 115.77(18) . . ?
C5 N2 C4 121.61(16) . . ?
C5 N3 C6 131.87(17) . . ?
O2 N4 O1 123.22(18) . . ?
O2 N4 C9 118.18(19) . . ?
O1 N4 C9 118.60(18) . . ?
S3 O3 S3' 47.7(3) . . ?
S3 C12 S3' 37.6(2) . . ?
S3' C13 S3 36.9(2) . . ?
S3 S3' O3 55.7(3) . . ?
S3 S3' C13 74.3(4) . . ?
O3 S3' C13 107.44(18) . . ?
S3 S3' C12 67.0(3) . . ?
O3 S3' C12 105.32(16) . . ?
C13 S3' C12 97.80(17) . . ?
S3' S3 O3 76.5(4) . . ?
S3' S3 C12 75.4(3) . . ?
O3 S3 C12 122.7(5) . . ?
S3' S3 C13 68.8(3) . . ?
O3 S3 C13 115.6(4) . . ?
C12 S3 C13 98.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1436503'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N8 O4 S4 Zn, 2(C2.80 H6.80 N O)'
_chemical_formula_sum            'C27.60 H31.60 N10 O6 S4 Zn'
_chemical_formula_weight         793.06

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'
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'
Zn Zn 0.2839 1.4301 '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           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   35.437(2)
_cell_length_b                   5.1812(3)
_cell_length_c                   19.7021(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.827(5)
_cell_angle_gamma                90.00
_cell_volume                     3604.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1836
_cell_measurement_theta_min      3.8870
_cell_measurement_theta_max      26.0540

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1636.8
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_process_details   multi-scan

_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  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2760
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6405
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3271
_reflns_number_gt                2266
_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)+(0.0000P)²+12.0000P] 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_number_reflns         3271
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Zn1 Zn 0.5000 0.28053(15) 0.7500 0.0491(2) Uani 1 2 d S . .
S2 S 0.44557(3) 0.0889(3) 0.70660(6) 0.0616(4) Uani 1 1 d . . .
S1 S 0.49805(3) 0.7663(3) 0.56081(6) 0.0695(4) Uani 1 1 d . . .
N1 N 0.50787(9) 0.5076(7) 0.67004(16) 0.0487(9) Uani 1 1 d . . .
N2 N 0.44727(9) 0.4553(7) 0.60360(16) 0.0537(10) Uani 1 1 d . . .
C4 C 0.48260(11) 0.5474(9) 0.6184(2) 0.0480(11) Uani 1 1 d . . .
N3 N 0.39327(10) 0.2258(8) 0.61473(18) 0.0636(11) Uani 1 1 d . . .
H3A H 0.3839 0.0929 0.6334 0.076 Uiso 1 1 calc R . .
O O 0.29280(12) 0.8864(11) 0.4004(2) 0.1185(17) Uani 1 1 d . . .
O4 O 0.25315(12) 0.5988(10) 0.4259(2) 0.1328(19) Uani 1 1 d . . .
C3 C 0.54020(12) 0.6527(9) 0.6637(2) 0.0557(12) Uani 1 1 d . . .
H3 H 0.5608 0.6454 0.6962 0.067 Uiso 1 1 calc R . .
C5 C 0.43039(11) 0.2821(9) 0.6371(2) 0.0496(11) Uani 1 1 d . . .
C6 C 0.36862(12) 0.3512(10) 0.5666(2) 0.0581(13) Uani 1 1 d . . .
C11 C 0.37706(13) 0.5576(12) 0.5272(3) 0.0847(18) Uani 1 1 d . . .
H11 H 0.4016 0.6222 0.5300 0.102 Uiso 1 1 calc R . .
N4 N 0.28458(13) 0.6961(12) 0.4317(2) 0.0904(16) Uani 1 1 d . . .
C2 C 0.54058(12) 0.8044(10) 0.6085(2) 0.0578(12) Uani 1 1 d . . .
C9 C 0.31384(14) 0.5735(12) 0.4778(2) 0.0723(15) Uani 1 1 d . . .
C7 C 0.33180(14) 0.2566(12) 0.5595(3) 0.0903(19) Uani 1 1 d . . .
H7 H 0.3255 0.1143 0.5850 0.108 Uiso 1 1 calc R . .
C10 C 0.34950(14) 0.6701(12) 0.4837(3) 0.0902(19) Uani 1 1 d . . .
H10 H 0.3553 0.8134 0.4582 0.108 Uiso 1 1 calc R . .
C1 C 0.57142(14) 0.9796(11) 0.5880(3) 0.0872(18) Uani 1 1 d . . .
H1A H 0.5919 0.9805 0.6231 0.131 Uiso 1 1 calc R . .
H1B H 0.5616 1.1514 0.5816 0.131 Uiso 1 1 calc R . .
H1C H 0.5804 0.9187 0.5463 0.131 Uiso 1 1 calc R . .
C8 C 0.30493(15) 0.3684(13) 0.5161(3) 0.101(2) Uani 1 1 d . . .
H8 H 0.2803 0.3042 0.5125 0.121 Uiso 1 1 calc R . .
O2A O 0.35180(14) 0.8419(11) 0.6886(3) 0.141(2) Uani 1 1 d . . .
C13 C 0.2855(2) 0.385(2) 0.7266(5) 0.197(5) Uani 1 1 d . . .
H13A H 0.2712 0.4390 0.6854 0.295 Uiso 1 1 calc R . .
H13B H 0.2711 0.4191 0.7648 0.295 Uiso 1 1 calc R . .
H13C H 0.2907 0.2039 0.7242 0.295 Uiso 1 1 calc R . .
C14 C 0.3258(3) 0.717(2) 0.6883(4) 0.112(3) Uani 0.80 1 d P . .
H14 H 0.3064 0.7439 0.6543 0.135 Uiso 0.80 1 calc PR . .
N5 N 0.3212(2) 0.5285(12) 0.7346(3) 0.125(2) Uani 1 1 d . . .
C12 C 0.3492(2) 0.449(2) 0.7851(4) 0.190(5) Uani 1 1 d . . .
H12A H 0.3731 0.5232 0.7760 0.285 Uiso 1 1 calc R . .
H12B H 0.3511 0.2644 0.7848 0.285 Uiso 1 1 calc R . .
H12C H 0.3425 0.5058 0.8289 0.285 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
Zn1 N1 2.005(3) 2_656 ?
Zn1 N1 2.005(3) . ?
Zn1 S2 2.2715(12) . ?
Zn1 S2 2.2715(12) 2_656 ?
S2 C5 1.745(4) . ?
S1 C2 1.719(4) . ?
S1 C4 1.725(4) . ?
N1 C4 1.314(5) . ?
N1 C3 1.385(5) . ?
N2 C5 1.290(5) . ?
N2 C4 1.349(5) . ?
N3 C5 1.383(5) . ?
N3 C6 1.395(5) . ?
O N4 1.213(6) . ?
O4 N4 1.219(6) . ?
C3 C2 1.342(6) . ?
C6 C11 1.369(6) . ?
C6 C7 1.390(6) . ?
C11 C10 1.374(6) . ?
N4 C9 1.464(6) . ?
C2 C1 1.502(6) . ?
C9 C10 1.355(7) . ?
C9 C8 1.356(7) . ?
C7 C8 1.356(7) . ?
O2A C14 1.126(10) . ?
C13 N5 1.463(9) . ?
C14 N5 1.353(10) . ?
N5 C12 1.407(9) . ?

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
N1 Zn1 N1 108.1(2) 2_656 . ?
N1 Zn1 S2 112.49(10) 2_656 . ?
N1 Zn1 S2 97.51(10) . . ?
N1 Zn1 S2 97.51(10) 2_656 2_656 ?
N1 Zn1 S2 112.49(10) . 2_656 ?
S2 Zn1 S2 128.15(8) . 2_656 ?
C5 S2 Zn1 103.92(15) . . ?
C2 S1 C4 91.6(2) . . ?
C4 N1 C3 111.1(4) . . ?
C4 N1 Zn1 124.8(3) . . ?
C3 N1 Zn1 124.1(3) . . ?
C5 N2 C4 126.7(4) . . ?
N1 C4 N2 132.2(4) . . ?
N1 C4 S1 112.3(3) . . ?
N2 C4 S1 115.5(3) . . ?
C5 N3 C6 130.0(4) . . ?
C2 C3 N1 117.1(4) . . ?
N2 C5 N3 117.0(4) . . ?
N2 C5 S2 132.5(3) . . ?
N3 C5 S2 110.6(3) . . ?
C11 C6 C7 117.9(4) . . ?
C11 C6 N3 126.5(4) . . ?
C7 C6 N3 115.6(4) . . ?
C6 C11 C10 120.5(5) . . ?
O N4 O4 123.0(5) . . ?
O N4 C9 118.7(5) . . ?
O4 N4 C9 118.2(6) . . ?
C3 C2 C1 129.0(4) . . ?
C3 C2 S1 107.9(3) . . ?
C1 C2 S1 123.1(4) . . ?
C10 C9 C8 120.0(5) . . ?
C10 C9 N4 120.0(6) . . ?
C8 C9 N4 119.9(5) . . ?
C8 C7 C6 121.0(5) . . ?
C9 C10 C11 120.4(5) . . ?
C7 C8 C9 120.2(5) . . ?
O2A C14 N5 123.9(9) . . ?
C14 N5 C12 124.6(8) . . ?
C14 N5 C13 116.5(8) . . ?
C12 N5 C13 118.7(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1436504'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N4 O2 S2'
_chemical_formula_sum            'C11 H10 N4 O2 S2'
_chemical_formula_weight         294.35

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6976(8)
_cell_length_b                   12.5934(9)
_cell_length_c                   14.4096(9)
_cell_angle_alpha                87.490(5)
_cell_angle_beta                 85.965(5)
_cell_angle_gamma                83.479(5)
_cell_volume                     1922.7(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1908
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      24.60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   multi-scan

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11109
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6599
_reflns_number_gt                4099
_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)+(0.0900P)²+0.0100P] 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         6599
_refine_ls_number_parameters     525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
S2 S 0.32921(13) 0.41280(9) 0.75115(7) 0.0505(4) Uani 1 1 d . . .
S1 S 0.29004(13) 0.21107(9) 0.66598(7) 0.0462(4) Uani 1 1 d . . .
O1 O 0.3446(4) 0.8037(3) 0.2291(2) 0.0740(12) Uani 1 1 d . . .
O2 O 0.3892(4) 0.9305(3) 0.3136(2) 0.0923(15) Uani 1 1 d . . .
N3 N 0.3493(4) 0.5644(3) 0.6221(2) 0.0438(10) Uani 1 1 d . . .
H4A H 0.3623 0.5975 0.6708 0.053 Uiso 1 1 calc R . .
N2 N 0.3155(4) 0.4036(3) 0.5644(2) 0.0416(10) Uani 1 1 d . . .
N4 N 0.3664(4) 0.8386(4) 0.3042(3) 0.0526(12) Uani 1 1 d . . .
N1 N 0.2951(4) 0.2479(3) 0.4921(2) 0.0492(11) Uani 1 1 d . . .
H1 H 0.2987 0.2796 0.4381 0.059 Uiso 1 1 calc R . .
C6 C 0.3515(4) 0.6272(3) 0.5393(3) 0.0408(12) Uani 1 1 d . . .
C7 C 0.3910(4) 0.7266(3) 0.5473(3) 0.0377(12) Uani 1 1 d . . .
H7 H 0.4140 0.7468 0.6045 0.045 Uiso 1 1 calc R . .
C8 C 0.3968(5) 0.7973(3) 0.4701(3) 0.0489(13) Uani 1 1 d . . .
H8 H 0.4249 0.8639 0.4753 0.059 Uiso 1 1 calc R . .
C9 C 0.3601(5) 0.7673(4) 0.3856(3) 0.0448(13) Uani 1 1 d . . .
C10 C 0.3204(5) 0.6687(4) 0.3781(3) 0.0564(15) Uani 1 1 d . . .
H10 H 0.2958 0.6494 0.3211 0.068 Uiso 1 1 calc R . .
C11 C 0.3162(5) 0.5968(4) 0.4539(3) 0.0548(15) Uani 1 1 d . . .
H11 H 0.2902 0.5296 0.4477 0.066 Uiso 1 1 calc R . .
C5 C 0.3299(4) 0.4590(3) 0.6387(3) 0.0379(12) Uani 1 1 d . . .
C4 C 0.3011(4) 0.3001(4) 0.5710(3) 0.0379(12) Uani 1 1 d . . .
C2 C 0.2784(5) 0.1050(3) 0.5932(3) 0.0485(13) Uani 1 1 d . . .
C3 C 0.2829(5) 0.1401(4) 0.5036(3) 0.0498(14) Uani 1 1 d . . .
H3A H 0.2782 0.0960 0.4542 0.060 Uiso 1 1 calc R . .
C1 C 0.2703(5) -0.0045(4) 0.6335(3) 0.0688(17) Uani 1 1 d . . .
H1A H 0.2454 -0.0489 0.5872 0.103 Uiso 1 1 calc R . .
H1B H 0.2092 -0.0018 0.6856 0.103 Uiso 1 1 calc R . .
H1C H 0.3511 -0.0335 0.6538 0.103 Uiso 1 1 calc R . .
S3 S 0.34197(12) 0.96388(9) -0.11628(7) 0.0443(4) Uani 1 1 d . . .
S4 S 0.35006(14) 0.75398(9) -0.20123(7) 0.0520(4) Uani 1 1 d . . .
O3 O 0.2791(4) 0.2501(3) 0.2470(2) 0.0733(12) Uani 1 1 d . . .
O4 O 0.3561(3) 0.3676(3) 0.3234(2) 0.0631(11) Uani 1 1 d . . .
N8 N 0.3200(4) 0.3362(3) 0.2505(3) 0.0517(12) Uani 1 1 d . . .
N7 N 0.3369(4) 0.6025(3) -0.0705(2) 0.0419(10) Uani 1 1 d . . .
H7A H 0.3343 0.5666 -0.1196 0.050 Uiso 1 1 calc R . .
N6 N 0.3436(4) 0.7681(3) -0.0130(2) 0.0436(10) Uani 1 1 d . . .
N5 N 0.3452(4) 0.9293(3) 0.0576(2) 0.0423(10) Uani 1 1 d . . .
C17 C 0.3330(4) 0.5420(3) 0.0129(3) 0.0360(11) Uani 1 1 d . . .
C22 C 0.2818(5) 0.4448(3) 0.0107(3) 0.0463(13) Uani 1 1 d . . .
H22 H 0.2507 0.4253 -0.0440 0.056 Uiso 1 1 calc R . .
C21 C 0.2770(5) 0.3777(3) 0.0885(3) 0.0456(13) Uani 1 1 d . . .
H21 H 0.2408 0.3141 0.0874 0.055 Uiso 1 1 calc R . .
C20 C 0.3267(4) 0.4066(4) 0.1682(3) 0.0398(12) Uani 1 1 d . . .
C19 C 0.3786(5) 0.5008(4) 0.1721(3) 0.0460(13) Uani 1 1 d . . .
H19 H 0.4116 0.5186 0.2266 0.055 Uiso 1 1 calc R . .
C18 C 0.3815(4) 0.5692(3) 0.0947(3) 0.0448(13) Uani 1 1 d . . .
H18 H 0.4159 0.6335 0.0972 0.054 Uiso 1 1 calc R . .
C16 C 0.3441(4) 0.7100(3) -0.0874(3) 0.0371(11) Uani 1 1 d . . .
C15 C 0.3440(4) 0.8743(3) -0.0207(3) 0.0392(12) Uani 1 1 d . . .
C13 C 0.3447(4) 1.0722(3) -0.0443(3) 0.0420(12) Uani 1 1 d . . .
C14 C 0.3468(4) 1.0381(3) 0.0454(3) 0.0466(13) Uani 1 1 d . . .
H14 H 0.3491 1.0836 0.0943 0.056 Uiso 1 1 calc R . .
C12 C 0.3484(5) 1.1817(3) -0.0859(3) 0.0595(16) Uani 1 1 d . . .
H12A H 0.2640 1.2137 -0.0944 0.089 Uiso 1 1 calc R . .
H12B H 0.3957 1.1781 -0.1451 0.089 Uiso 1 1 calc R . .
H12C H 0.3880 1.2240 -0.0452 0.089 Uiso 1 1 calc R . .
S5 S 0.02677(13) 0.87838(9) 0.10967(7) 0.0435(4) Uani 1 1 d . . .
S6 S 0.01003(13) 0.67168(9) 0.02282(7) 0.0457(4) Uani 1 1 d . . .
O6 O -0.0012(4) 0.2906(3) 0.5501(2) 0.0660(11) Uani 1 1 d . . .
O5 O -0.0582(4) 0.1668(3) 0.4701(2) 0.0744(12) Uani 1 1 d . . .
N9 N 0.0414(4) 0.8390(3) 0.2816(3) 0.0488(12) Uani 1 1 d . . .
N10 N 0.0264(4) 0.6819(3) 0.2093(2) 0.0402(10) Uani 1 1 d . . .
N11 N 0.0012(3) 0.5189(3) 0.1524(2) 0.0390(10) Uani 1 1 d . . .
H11A H -0.0046 0.4833 0.1035 0.047 Uiso 1 1 calc R . .
N12 N -0.0261(4) 0.2557(3) 0.4758(3) 0.0497(11) Uani 1 1 d . . .
C28 C -0.0035(4) 0.4587(3) 0.2357(3) 0.0365(11) Uani 1 1 d . . .
C29 C 0.0436(5) 0.4862(3) 0.3186(3) 0.0456(13) Uani 1 1 d . . .
H29 H 0.0793 0.5499 0.3214 0.055 Uiso 1 1 calc R . .
C30 C 0.0367(5) 0.4183(3) 0.3960(3) 0.0444(13) Uani 1 1 d . . .
H30 H 0.0683 0.4362 0.4511 0.053 Uiso 1 1 calc R . .
C31 C -0.0161(5) 0.3249(3) 0.3926(3) 0.0407(12) Uani 1 1 d . . .
C32 C -0.0646(5) 0.2959(3) 0.3118(3) 0.0467(13) Uani 1 1 d . . .
H32 H -0.1024 0.2330 0.3105 0.056 Uiso 1 1 calc R . .
C33 C -0.0559(5) 0.3618(3) 0.2335(3) 0.0451(13) Uani 1 1 d . . .
H33 H -0.0852 0.3419 0.1782 0.054 Uiso 1 1 calc R . .
C27 C 0.0135(4) 0.6256(3) 0.1350(3) 0.0379(11) Uani 1 1 d . . .
C26 C 0.0314(4) 0.7862(3) 0.2038(3) 0.0380(12) Uani 1 1 d . . .
C25 C 0.0469(5) 0.9473(4) 0.2700(3) 0.0526(14) Uani 1 1 d . . .
H25 H 0.0545 0.9912 0.3191 0.063 Uiso 1 1 calc R . .
C24 C 0.0405(5) 0.9837(3) 0.1822(3) 0.0459(13) Uani 1 1 d . . .
C23 C 0.0365(5) 1.0956(3) 0.1440(3) 0.0615(16) Uani 1 1 d . . .
H23A H -0.0489 1.1227 0.1330 0.092 Uiso 1 1 calc R . .
H23B H 0.0875 1.0971 0.0865 0.092 Uiso 1 1 calc R . .
H23C H 0.0684 1.1393 0.1878 0.092 Uiso 1 1 calc R . .
H5A H 0.346(4) 0.897(3) 0.118(3) 0.043(12) Uiso 1 1 d . . .
H9A H 0.040(4) 0.803(3) 0.330(3) 0.044(14) 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 C5 1.698(4) . ?
S1 C4 1.737(4) . ?
S1 C2 1.755(4) . ?
O1 N4 1.232(4) . ?
O2 N4 1.225(5) . ?
N3 C5 1.375(5) . ?
N3 C6 1.402(5) . ?
N3 H4A 0.8600 . ?
N2 C4 1.328(5) . ?
N2 C5 1.329(5) . ?
N4 C9 1.448(5) . ?
N1 C4 1.347(5) . ?
N1 C3 1.380(5) . ?
N1 H1 0.8600 . ?
C6 C7 1.379(6) . ?
C6 C11 1.394(5) . ?
C7 C8 1.397(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(6) . ?
C10 C11 1.389(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C2 C3 1.345(5) . ?
C2 C1 1.482(6) . ?
C3 H3A 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
S3 C15 1.741(4) . ?
S3 C13 1.754(4) . ?
S4 C16 1.707(4) . ?
O3 N8 1.219(5) . ?
O4 N8 1.240(4) . ?
N8 C20 1.452(5) . ?
N7 C16 1.375(5) . ?
N7 C17 1.396(5) . ?
N7 H7A 0.8600 . ?
N6 C16 1.324(5) . ?
N6 C15 1.338(5) . ?
N5 C15 1.351(5) . ?
N5 C14 1.376(5) . ?
N5 H5A 0.95(4) . ?
C17 C18 1.391(5) . ?
C17 C22 1.399(6) . ?
C22 C21 1.376(5) . ?
C22 H22 0.9300 . ?
C21 C20 1.378(5) . ?
C21 H21 0.9300 . ?
C20 C19 1.371(6) . ?
C19 C18 1.380(5) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C13 C14 1.345(5) . ?
C13 C12 1.482(6) . ?
C14 H14 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
S5 C26 1.746(4) . ?
S5 C24 1.749(4) . ?
S6 C27 1.695(4) . ?
O6 N12 1.232(4) . ?
O5 N12 1.216(5) . ?
N9 C26 1.345(5) . ?
N9 C25 1.374(6) . ?
N9 H9A 0.82(4) . ?
N10 C26 1.319(5) . ?
N10 C27 1.333(5) . ?
N11 C27 1.376(5) . ?
N11 C28 1.393(5) . ?
N11 H11A 0.8600 . ?
N12 C31 1.456(5) . ?
C28 C29 1.400(5) . ?
C28 C33 1.402(6) . ?
C29 C30 1.379(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.365(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.388(5) . ?
C32 C33 1.375(5) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C25 C24 1.330(5) . ?
C25 H25 0.9300 . ?
C24 C23 1.488(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C4 S1 C2 91.5(2) . . ?
C5 N3 C6 131.1(4) . . ?
C5 N3 H4A 114.5 . . ?
C6 N3 H4A 114.5 . . ?
C4 N2 C5 121.9(4) . . ?
O2 N4 O1 123.5(4) . . ?
O2 N4 C9 118.8(4) . . ?
O1 N4 C9 117.6(4) . . ?
C4 N1 C3 115.7(4) . . ?
C4 N1 H1 122.2 . . ?
C3 N1 H1 122.2 . . ?
C7 C6 C11 120.0(4) . . ?
C7 C6 N3 114.7(4) . . ?
C11 C6 N3 125.3(4) . . ?
C6 C7 C8 120.4(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 N4 119.4(4) . . ?
C8 C9 N4 120.5(4) . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C6 118.9(4) . . ?
C10 C11 H11 120.6 . . ?
C6 C11 H11 120.6 . . ?
N2 C5 N3 116.2(4) . . ?
N2 C5 S2 127.0(3) . . ?
N3 C5 S2 116.8(3) . . ?
N2 C4 N1 118.5(4) . . ?
N2 C4 S1 132.2(3) . . ?
N1 C4 S1 109.3(3) . . ?
C3 C2 C1 129.8(4) . . ?
C3 C2 S1 110.0(3) . . ?
C1 C2 S1 120.1(3) . . ?
C2 C3 N1 113.6(4) . . ?
C2 C3 H3A 123.2 . . ?
N1 C3 H3A 123.2 . . ?
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 . . ?
C15 S3 C13 91.4(2) . . ?
O3 N8 O4 122.1(4) . . ?
O3 N8 C20 120.4(4) . . ?
O4 N8 C20 117.5(4) . . ?
C16 N7 C17 130.8(3) . . ?
C16 N7 H7A 114.6 . . ?
C17 N7 H7A 114.6 . . ?
C16 N6 C15 121.2(4) . . ?
C15 N5 C14 116.1(4) . . ?
C15 N5 H5A 123(2) . . ?
C14 N5 H5A 120(2) . . ?
C18 C17 N7 124.7(4) . . ?
C18 C17 C22 119.0(4) . . ?
N7 C17 C22 116.1(4) . . ?
C21 C22 C17 120.7(4) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C22 C21 C20 118.8(4) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C19 C20 C21 121.7(4) . . ?
C19 C20 N8 119.7(4) . . ?
C21 C20 N8 118.6(4) . . ?
C20 C19 C18 119.6(4) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N6 C16 N7 115.9(3) . . ?
N6 C16 S4 127.4(3) . . ?
N7 C16 S4 116.7(3) . . ?
N6 C15 N5 118.6(4) . . ?
N6 C15 S3 132.5(3) . . ?
N5 C15 S3 108.9(3) . . ?
C14 C13 C12 129.6(4) . . ?
C14 C13 S3 110.3(3) . . ?
C12 C13 S3 120.0(3) . . ?
C13 C14 N5 113.2(4) . . ?
C13 C14 H14 123.4 . . ?
N5 C14 H14 123.4 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C26 S5 C24 91.6(2) . . ?
C26 N9 C25 116.1(4) . . ?
C26 N9 H9A 116(3) . . ?
C25 N9 H9A 128(3) . . ?
C26 N10 C27 122.4(4) . . ?
C27 N11 C28 130.9(3) . . ?
C27 N11 H11A 114.6 . . ?
C28 N11 H11A 114.6 . . ?
O5 N12 O6 122.5(4) . . ?
O5 N12 C31 119.8(4) . . ?
O6 N12 C31 117.8(4) . . ?
N11 C28 C29 125.0(4) . . ?
N11 C28 C33 116.1(4) . . ?
C29 C28 C33 118.9(4) . . ?
C30 C29 C28 119.6(4) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C31 C30 C29 120.6(4) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 121.2(4) . . ?
C30 C31 N12 119.9(4) . . ?
C32 C31 N12 118.9(4) . . ?
C33 C32 C31 118.8(4) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C32 C33 C28 120.9(4) . . ?
C32 C33 H33 119.5 . . ?
C28 C33 H33 119.5 . . ?
N10 C27 N11 115.8(4) . . ?
N10 C27 S6 127.0(3) . . ?
N11 C27 S6 117.2(3) . . ?
N10 C26 N9 119.6(4) . . ?
N10 C26 S5 132.0(3) . . ?
N9 C26 S5 108.4(3) . . ?
C24 C25 N9 113.9(4) . . ?
C24 C25 H25 123.0 . . ?
N9 C25 H25 123.0 . . ?
C25 C24 C23 129.2(4) . . ?
C25 C24 S5 110.1(3) . . ?
C23 C24 S5 120.7(3) . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C5 N3 C6 C7 -171.5(4) . . . . ?
C5 N3 C6 C11 9.4(8) . . . . ?
C11 C6 C7 C8 -0.4(7) . . . . ?
N3 C6 C7 C8 -179.6(4) . . . . ?
C6 C7 C8 C9 1.2(7) . . . . ?
C7 C8 C9 C10 -0.9(7) . . . . ?
C7 C8 C9 N4 -179.3(4) . . . . ?
O2 N4 C9 C10 172.4(5) . . . . ?
O1 N4 C9 C10 -5.5(7) . . . . ?
O2 N4 C9 C8 -9.1(7) . . . . ?
O1 N4 C9 C8 173.0(4) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
N4 C9 C10 C11 178.3(4) . . . . ?
C9 C10 C11 C6 0.9(7) . . . . ?
C7 C6 C11 C10 -0.6(7) . . . . ?
N3 C6 C11 C10 178.4(4) . . . . ?
C4 N2 C5 N3 177.3(4) . . . . ?
C4 N2 C5 S2 -1.6(7) . . . . ?
C6 N3 C5 N2 3.1(7) . . . . ?
C6 N3 C5 S2 -177.8(4) . . . . ?
C5 N2 C4 N1 -175.8(4) . . . . ?
C5 N2 C4 S1 2.9(7) . . . . ?
C3 N1 C4 N2 178.6(4) . . . . ?
C3 N1 C4 S1 -0.4(5) . . . . ?
C2 S1 C4 N2 -178.5(5) . . . . ?
C2 S1 C4 N1 0.3(3) . . . . ?
C4 S1 C2 C3 -0.2(4) . . . . ?
C4 S1 C2 C1 177.8(4) . . . . ?
C1 C2 C3 N1 -177.7(5) . . . . ?
S1 C2 C3 N1 0.0(5) . . . . ?
C4 N1 C3 C2 0.3(6) . . . . ?
C16 N7 C17 C18 -25.3(7) . . . . ?
C16 N7 C17 C22 158.1(4) . . . . ?
C18 C17 C22 C21 1.3(7) . . . . ?
N7 C17 C22 C21 178.1(4) . . . . ?
C17 C22 C21 C20 -1.8(7) . . . . ?
C22 C21 C20 C19 1.1(7) . . . . ?
C22 C21 C20 N8 179.2(4) . . . . ?
O3 N8 C20 C19 -176.8(5) . . . . ?
O4 N8 C20 C19 3.8(6) . . . . ?
O3 N8 C20 C21 5.0(7) . . . . ?
O4 N8 C20 C21 -174.4(4) . . . . ?
C21 C20 C19 C18 0.0(7) . . . . ?
N8 C20 C19 C18 -178.0(4) . . . . ?
C20 C19 C18 C17 -0.6(7) . . . . ?
N7 C17 C18 C19 -176.6(4) . . . . ?
C22 C17 C18 C19 -0.1(7) . . . . ?
C15 N6 C16 N7 -176.7(4) . . . . ?
C15 N6 C16 S4 2.1(7) . . . . ?
C17 N7 C16 N6 -2.4(7) . . . . ?
C17 N7 C16 S4 178.7(4) . . . . ?
C16 N6 C15 N5 -179.1(4) . . . . ?
C16 N6 C15 S3 1.5(7) . . . . ?
C14 N5 C15 N6 179.4(4) . . . . ?
C14 N5 C15 S3 -1.1(5) . . . . ?
C13 S3 C15 N6 -179.9(5) . . . . ?
C13 S3 C15 N5 0.6(3) . . . . ?
C15 S3 C13 C14 -0.1(4) . . . . ?
C15 S3 C13 C12 178.1(4) . . . . ?
C12 C13 C14 N5 -178.4(4) . . . . ?
S3 C13 C14 N5 -0.5(5) . . . . ?
C15 N5 C14 C13 1.1(6) . . . . ?
C27 N11 C28 C29 -21.9(7) . . . . ?
C27 N11 C28 C33 160.3(4) . . . . ?
N11 C28 C29 C30 -178.1(4) . . . . ?
C33 C28 C29 C30 -0.5(7) . . . . ?
C28 C29 C30 C31 -0.3(7) . . . . ?
C29 C30 C31 C32 -0.3(7) . . . . ?
C29 C30 C31 N12 -178.1(4) . . . . ?
O5 N12 C31 C30 -170.7(5) . . . . ?
O6 N12 C31 C30 9.2(7) . . . . ?
O5 N12 C31 C32 11.4(7) . . . . ?
O6 N12 C31 C32 -168.7(4) . . . . ?
C30 C31 C32 C33 1.7(7) . . . . ?
N12 C31 C32 C33 179.5(4) . . . . ?
C31 C32 C33 C28 -2.5(7) . . . . ?
N11 C28 C33 C32 179.7(4) . . . . ?
C29 C28 C33 C32 1.9(7) . . . . ?
C26 N10 C27 N11 -175.8(4) . . . . ?
C26 N10 C27 S6 3.9(7) . . . . ?
C28 N11 C27 N10 1.8(7) . . . . ?
C28 N11 C27 S6 -177.8(4) . . . . ?
C27 N10 C26 N9 178.4(4) . . . . ?
C27 N10 C26 S5 -1.3(7) . . . . ?
C25 N9 C26 N10 179.6(4) . . . . ?
C25 N9 C26 S5 -0.7(5) . . . . ?
C24 S5 C26 N10 -179.7(5) . . . . ?
C24 S5 C26 N9 0.6(3) . . . . ?
C26 N9 C25 C24 0.4(7) . . . . ?
N9 C25 C24 C23 176.3(5) . . . . ?
N9 C25 C24 S5 0.0(6) . . . . ?
C26 S5 C24 C25 -0.3(4) . . . . ?
C26 S5 C24 C23 -177.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1436505'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 Br N4 O3 S, C2 H6 O S'
_chemical_formula_sum            'C13 H15 Br N4 O4 S2'
_chemical_formula_weight         435.31

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2653(7)
_cell_length_b                   10.2683(7)
_cell_length_c                   11.4407(8)
_cell_angle_alpha                66.570(4)
_cell_angle_beta                 80.387(5)
_cell_angle_gamma                65.245(5)
_cell_volume                     906.93(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1534
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      17.82

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    2.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_T_max  0.739
_exptl_absorpt_process_details   multi-scan

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13108
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3255
_reflns_number_gt                1699
_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)+(0.0000P)²+1.9000P] 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         3255
_refine_ls_number_parameters     208
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      3.545
_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
C6 C 0.8923(16) 0.7047(16) 0.7715(12) 0.065(6) Uani 1 1 d GD . .
C7 C 0.7412(16) 0.8167(14) 0.7329(13) 0.076(6) Uani 1 1 d GD . .
H7 H 0.6924 0.8900 0.7707 0.091 Uiso 1 1 calc R . .
C8 C 0.6630(13) 0.8192(15) 0.6379(14) 0.083(7) Uani 1 1 d G . .
H8A H 0.5619 0.8942 0.6121 0.099 Uiso 1 1 calc R . .
C9 C 0.7360(17) 0.7098(17) 0.5814(12) 0.071(6) Uani 1 1 d G . .
C10 C 0.8871(17) 0.5978(15) 0.6200(13) 0.080(7) Uani 1 1 d G . .
H10 H 0.9359 0.5246 0.5823 0.096 Uiso 1 1 calc R . .
C11 C 0.9652(13) 0.5953(14) 0.7151(13) 0.078(7) Uani 1 1 d G . .
H11 H 1.0664 0.5204 0.7409 0.094 Uiso 1 1 calc R . .
S1 S 0.8365(7) 0.9391(7) 1.1359(6) 0.0779(18) Uani 1 1 d D . .
C2 C 1.073(3) 0.827(3) 1.286(2) 0.073(6) Uani 1 1 d . . .
C3 C 0.925(3) 0.929(3) 1.2636(19) 0.073(6) Uani 1 1 d . . .
C4 C 1.014(3) 0.796(2) 1.122(2) 0.065(6) Uani 1 1 d . . .
N3 N 0.9764(19) 0.6939(19) 0.8660(15) 0.070(5) Uani 1 1 d . . .
H3 H 1.0714 0.6245 0.8799 0.084 Uiso 1 1 calc R . .
N1 N 1.125(2) 0.750(2) 1.2017(17) 0.073(5) Uani 1 1 d . . .
N2 N 1.038(2) 0.7323(19) 1.0306(16) 0.073(5) Uani 1 1 d . . .
H2 H 1.1273 0.6585 1.0294 0.088 Uiso 1 1 calc R . .
Br1 Br 0.8064(3) 1.0634(3) 1.3513(3) 0.1049(12) Uani 1 1 d . . .
C1 C 1.182(3) 0.791(3) 1.386(2) 0.103(9) Uani 1 1 d . . .
H1A H 1.2716 0.8161 1.3470 0.154 Uiso 1 1 calc R . .
H1B H 1.2175 0.6836 1.4382 0.154 Uiso 1 1 calc R . .
H1C H 1.1259 0.8512 1.4381 0.154 Uiso 1 1 calc R . .
S2 S 0.5503(7) 0.6040(8) 0.0698(7) 0.088(2) Uani 1 1 d . . .
C5 C 0.924(3) 0.783(3) 0.941(2) 0.066(6) Uani 1 1 d . . .
O1 O 0.7991(17) 0.8879(17) 0.9331(13) 0.078(4) Uani 1 1 d . . .
N4 N 0.660(3) 0.710(3) 0.479(2) 0.091(6) Uani 1 1 d D . .
O2 O 0.732(2) 0.616(2) 0.4289(17) 0.125(7) Uani 1 1 d D . .
O3 O 0.526(2) 0.805(2) 0.450(2) 0.138(8) Uani 1 1 d D . .
O4 O 0.7219(16) 0.5289(17) 0.0434(14) 0.094(5) Uani 1 1 d . . .
C12 C 0.516(3) 0.487(3) 0.220(3) 0.138(12) Uani 1 1 d . . .
H12A H 0.5323 0.3889 0.2190 0.207 Uiso 1 1 calc R . .
H12B H 0.4085 0.5348 0.2455 0.207 Uiso 1 1 calc R . .
H12C H 0.5879 0.4725 0.2801 0.207 Uiso 1 1 calc R . .
C13 C 0.527(3) 0.764(3) 0.105(2) 0.105(8) Uani 1 1 d . . .
H13A H 0.5943 0.7300 0.1751 0.158 Uiso 1 1 calc R . .
H13B H 0.4183 0.8123 0.1265 0.158 Uiso 1 1 calc R . .
H13C H 0.5561 0.8359 0.0315 0.158 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
C6 C7 1.3900 . ?
C6 C11 1.3900 . ?
C6 N3 1.378(17) . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C9 N4 1.46(2) . ?
C10 C11 1.3900 . ?
S1 C4 1.72(2) . ?
S1 C3 1.74(2) . ?
C2 C3 1.32(3) . ?
C2 N1 1.38(2) . ?
C2 C1 1.49(3) . ?
C3 Br1 1.89(2) . ?
C4 N1 1.29(2) . ?
C4 N2 1.38(2) . ?
N3 C5 1.38(2) . ?
N2 C5 1.39(2) . ?
S2 O4 1.488(14) . ?
S2 C12 1.73(3) . ?
S2 C13 1.76(2) . ?
C5 O1 1.20(2) . ?
N4 O3 1.21(2) . ?
N4 O2 1.22(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
C7 C6 C11 120.0 . . ?
C7 C6 N3 123.3(12) . . ?
C11 C6 N3 116.7(12) . . ?
C8 C7 C6 120.0 . . ?
C9 C8 C7 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 N4 121.9(13) . . ?
C10 C9 N4 118.1(13) . . ?
C9 C10 C11 120.0 . . ?
C10 C11 C6 120.0 . . ?
C4 S1 C3 85.7(10) . . ?
C3 C2 N1 113(2) . . ?
C3 C2 C1 127(2) . . ?
N1 C2 C1 120(2) . . ?
C2 C3 S1 113.9(16) . . ?
C2 C3 Br1 127.6(17) . . ?
S1 C3 Br1 118.5(13) . . ?
N1 C4 N2 121.4(19) . . ?
N1 C4 S1 116.6(15) . . ?
N2 C4 S1 122.0(17) . . ?
C5 N3 C6 126.9(17) . . ?
C4 N1 C2 111.3(18) . . ?
C4 N2 C5 122.9(18) . . ?
O4 S2 C12 105.9(11) . . ?
O4 S2 C13 107.1(10) . . ?
C12 S2 C13 99.0(13) . . ?
O1 C5 N3 127(2) . . ?
O1 C5 N2 122.7(18) . . ?
N3 C5 N2 110(2) . . ?
O3 N4 O2 124(2) . . ?
O3 N4 C9 117.2(19) . . ?
O2 N4 C9 119(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1445143'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N4 O2 S2'
_chemical_formula_sum            'C11 H10 N4 O2 S2'
_chemical_formula_weight         294.35

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   24.0180(18)
_cell_length_b                   4.9616(2)
_cell_length_c                   23.5481(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.834(9)
_cell_angle_gamma                90.00
_cell_volume                     2586.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1414
_cell_measurement_theta_min      3.4156
_cell_measurement_theta_max      28.5612

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   multi-scan

_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  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4565
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2324
_reflns_number_gt                1834
_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)+(0.0900P)²+0.0078P] 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         2324
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.29343(3) -0.00903(13) 0.30818(3) 0.0464(3) Uani 1 1 d . . .
S2 S 0.24600(3) 0.11672(14) 0.40684(3) 0.0489(3) Uani 1 1 d . . .
N2 N 0.34485(10) 0.3718(4) 0.40294(10) 0.0411(5) Uani 1 1 d . . .
O1 O 0.54378(10) 1.2218(4) 0.61395(11) 0.0706(7) Uani 1 1 d . . .
N3 N 0.31856(11) 0.4667(4) 0.48438(10) 0.0403(5) Uani 1 1 d . . .
N1 N 0.37520(12) 0.3318(5) 0.32224(11) 0.0475(6) Uani 1 1 d . . .
O2 O 0.48629(12) 1.3435(5) 0.66033(12) 0.0873(9) Uani 1 1 d . . .
N4 N 0.49665(12) 1.2027(5) 0.62291(11) 0.0545(6) Uani 1 1 d . . .
C4 C 0.33948(12) 0.2513(5) 0.35041(12) 0.0384(6) Uani 1 1 d . . .
C6 C 0.36465(11) 0.6500(5) 0.51583(11) 0.0367(6) Uani 1 1 d . . .
C5 C 0.30715(12) 0.3251(5) 0.43065(12) 0.0378(6) Uani 1 1 d . . .
C9 C 0.45112(12) 1.0127(5) 0.58576(12) 0.0417(6) Uani 1 1 d . . .
C8 C 0.39556(13) 1.0113(5) 0.59060(12) 0.0437(7) Uani 1 1 d . . .
H8 H 0.3874 1.1306 0.6169 0.052 Uiso 1 1 calc R . .
C7 C 0.35228(12) 0.8289(5) 0.55556(12) 0.0410(6) Uani 1 1 d . . .
H7 H 0.3147 0.8249 0.5584 0.049 Uiso 1 1 calc R . .
C2 C 0.36889(14) 0.2019(6) 0.26791(13) 0.0529(7) Uani 1 1 d . . .
C3 C 0.32691(14) 0.0094(6) 0.25492(14) 0.0539(8) Uani 1 1 d . . .
H3 H 0.3167 -0.1032 0.2208 0.065 Uiso 1 1 calc R . .
C11 C 0.42091(12) 0.6587(5) 0.51132(13) 0.0449(7) Uani 1 1 d . . .
H11 H 0.4292 0.5433 0.4845 0.054 Uiso 1 1 calc R . .
C10 C 0.46415(13) 0.8388(5) 0.54680(13) 0.0466(7) Uani 1 1 d . . .
H10 H 0.5019 0.8432 0.5445 0.056 Uiso 1 1 calc R . .
C1 C 0.40707(18) 0.2893(8) 0.23388(17) 0.0891(13) Uani 1 1 d . . .
H1A H 0.4464 0.2093 0.2526 0.134 Uiso 1 1 calc R . .
H1B H 0.4108 0.4820 0.2355 0.134 Uiso 1 1 calc R . .
H1C H 0.3885 0.2324 0.1917 0.134 Uiso 1 1 calc R . .
H3A H 0.2935(12) 0.436(5) 0.4983(13) 0.039(8) Uiso 1 1 d . . .
H1 H 0.3937(13) 0.447(5) 0.3360(14) 0.041(9) 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 C3 1.735(3) . ?
S1 C4 1.740(3) . ?
S2 C5 1.703(3) . ?
N2 C5 1.326(3) . ?
N2 C4 1.334(3) . ?
O1 N4 1.233(3) . ?
N3 C5 1.379(3) . ?
N3 C6 1.402(3) . ?
N1 C4 1.333(3) . ?
N1 C2 1.387(3) . ?
O2 N4 1.223(3) . ?
N4 C9 1.452(3) . ?
C6 C11 1.397(4) . ?
C6 C7 1.403(3) . ?
C9 C10 1.381(4) . ?
C9 C8 1.383(4) . ?
C8 C7 1.384(4) . ?
C2 C3 1.335(4) . ?
C2 C1 1.497(4) . ?
C11 C10 1.379(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C4 90.21(13) . . ?
C5 N2 C4 122.6(2) . . ?
C5 N3 C6 130.6(2) . . ?
C4 N1 C2 117.3(2) . . ?
O2 N4 O1 122.4(2) . . ?
O2 N4 C9 119.3(3) . . ?
O1 N4 C9 118.3(2) . . ?
N1 C4 N2 118.5(2) . . ?
N1 C4 S1 109.10(19) . . ?
N2 C4 S1 132.4(2) . . ?
C11 C6 N3 124.7(2) . . ?
C11 C6 C7 119.6(2) . . ?
N3 C6 C7 115.8(2) . . ?
N2 C5 N3 115.6(2) . . ?
N2 C5 S2 127.6(2) . . ?
N3 C5 S2 116.77(19) . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 N4 119.6(3) . . ?
C8 C9 N4 118.6(2) . . ?
C9 C8 C7 118.7(2) . . ?
C8 C7 C6 120.5(2) . . ?
C3 C2 N1 110.2(3) . . ?
C3 C2 C1 130.5(3) . . ?
N1 C2 C1 119.3(3) . . ?
C2 C3 S1 113.1(2) . . ?
C10 C11 C6 119.8(2) . . ?
C11 C10 C9 119.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1445144'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N4 O2 S2, C4 H9 N O'
_chemical_formula_sum            'C15 H19 N5 O3 S2'
_chemical_formula_weight         381.47

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6923(2)
_cell_length_b                   9.6622(2)
_cell_length_c                   11.9422(3)
_cell_angle_alpha                106.3890(10)
_cell_angle_beta                 91.6680(10)
_cell_angle_gamma                107.4030(10)
_cell_volume                     911.10(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7050
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.37

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   multi-scan

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13899
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3258
_reflns_number_gt                2775
_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)+(0.1000P)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_number_reflns         3258
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.005

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 0.31798(5) 0.07066(5) 0.12337(4) 0.05386(18) Uani 1 1 d . . .
S2 S 0.47209(6) 0.02596(5) 0.32855(4) 0.06213(19) Uani 1 1 d . . .
C6 C 0.40919(18) 0.33323(17) 0.61188(14) 0.0467(4) Uani 1 1 d . . .
C8 C 0.4232(2) 0.4427(2) 0.82172(16) 0.0613(5) Uani 1 1 d . . .
H8 H 0.4526 0.4455 0.8980 0.074 Uiso 1 1 calc R . .
C9 C 0.3498(2) 0.54446(18) 0.80180(15) 0.0513(4) Uani 1 1 d . . .
C11 C 0.3394(2) 0.43947(18) 0.59401(15) 0.0519(4) Uani 1 1 d . . .
H11 H 0.3132 0.4400 0.5181 0.062 Uiso 1 1 calc R . .
C10 C 0.3095(2) 0.54343(18) 0.68931(15) 0.0526(4) Uani 1 1 d . . .
H10 H 0.2619 0.6133 0.6774 0.063 Uiso 1 1 calc R . .
C7 C 0.4516(2) 0.3386(2) 0.72755(16) 0.0595(5) Uani 1 1 d . . .
H7 H 0.5000 0.2697 0.7404 0.071 Uiso 1 1 calc R . .
C5 C 0.40493(18) 0.16975(17) 0.40307(14) 0.0472(4) Uani 1 1 d . . .
C4 C 0.28257(19) 0.20627(17) 0.24298(14) 0.0471(4) Uani 1 1 d . . .
C2 C 0.2242(2) 0.1323(2) 0.02468(16) 0.0618(5) Uani 1 1 d . . .
C3 C 0.1714(3) 0.2462(2) 0.08222(17) 0.0679(5) Uani 1 1 d . . .
H3 H 0.1185 0.2943 0.0445 0.081 Uiso 1 1 calc R . .
C1 C 0.2114(3) 0.0604(3) -0.10569(17) 0.0828(6) Uani 1 1 d . . .
H1A H 0.1668 0.1155 -0.1460 0.124 Uiso 1 1 calc R . .
H1B H 0.1417 -0.0434 -0.1269 0.124 Uiso 1 1 calc R . .
H1C H 0.3174 0.0633 -0.1276 0.124 Uiso 1 1 calc R . .
N3 N 0.44067(19) 0.21867(17) 0.52355(13) 0.0543(4) Uani 1 1 d . . .
N2 N 0.32022(16) 0.24007(14) 0.35855(11) 0.0475(3) Uani 1 1 d . . .
N1 N 0.2030(2) 0.28574(18) 0.20321(14) 0.0592(4) Uani 1 1 d . . .
N4 N 0.3127(2) 0.65113(18) 0.90215(15) 0.0649(4) Uani 1 1 d . . .
O1 O 0.2271(2) 0.72373(19) 0.88424(16) 0.0933(5) Uani 1 1 d . . .
O2 O 0.3701(2) 0.6651(2) 1.00129(14) 0.0992(6) Uani 1 1 d . . .
O3 O 0.1408(2) 0.53271(18) 0.34912(17) 0.0928(5) Uani 1 1 d . . .
C14 C 0.0858(4) 0.7408(4) 0.5182(2) 0.0830(6) Uani 1 1 d . . .
C13 C 0.0326(4) 0.8666(3) 0.3605(4) 0.0983(9) Uani 1 1 d . . .
C12 C 0.0938(4) 0.6405(4) 0.1892(3) 0.0949(8) Uani 1 1 d . . .
N5 N 0.0804(6) 0.7220(8) 0.3148(7) 0.0745(12) Uani 0.40 1 d P . .
C15 C 0.1051(7) 0.6550(9) 0.3891(9) 0.0707(14) Uani 0.40 1 d P . .
N5' N 0.0764(3) 0.7470(4) 0.3965(4) 0.0597(6) Uani 0.60 1 d P . .
C15' C 0.1049(5) 0.6325(5) 0.3123(5) 0.0601(9) Uani 0.60 1 d P . .
H1 H 0.482(2) 0.173(2) 0.5500(17) 0.052(5) Uiso 1 1 d . . .
H2 H 0.186(2) 0.368(2) 0.247(2) 0.072(6) Uiso 1 1 d . . .
H14A H 0.074(4) 0.652(4) 0.527(3) 0.154(15) Uiso 1 1 d . . .
H14B H -0.020(4) 0.756(4) 0.533(3) 0.147(12) Uiso 1 1 d . . .
H14C H 0.192(4) 0.828(4) 0.561(3) 0.133(10) Uiso 1 1 d . . .
H13C H 0.106(5) 0.942(5) 0.431(4) 0.170(16) Uiso 1 1 d . . .
H13B H -0.069(4) 0.855(4) 0.367(3) 0.122(11) Uiso 1 1 d . . .
H13A H 0.083(4) 0.905(4) 0.301(3) 0.152(13) Uiso 1 1 d . . .
H12B H 0.111(5) 0.550(5) 0.145(4) 0.175(16) Uiso 1 1 d . . .
H12A H -0.021(4) 0.624(3) 0.150(3) 0.131(11) Uiso 1 1 d . . .
H12C H 0.162(4) 0.728(4) 0.169(3) 0.135(10) 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 C2 1.7432(19) . ?
S1 C4 1.7500(16) . ?
S2 C5 1.6973(16) . ?
C6 N3 1.397(2) . ?
C6 C11 1.399(2) . ?
C6 C7 1.402(2) . ?
C8 C7 1.365(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.375(2) . ?
C9 N4 1.458(2) . ?
C11 C10 1.378(2) . ?
C5 N2 1.329(2) . ?
C5 N3 1.376(2) . ?
C4 N2 1.332(2) . ?
C4 N1 1.341(2) . ?
C2 C3 1.337(3) . ?
C2 C1 1.501(3) . ?
C3 N1 1.383(3) . ?
N4 O1 1.216(2) . ?
N4 O2 1.226(2) . ?
O3 C15 1.277(9) . ?
O3 C15' 1.277(6) . ?
C14 N5' 1.473(5) . ?
C14 C15 1.572(11) . ?
C13 N5' 1.483(5) . ?
C13 N5 1.533(8) . ?
C12 C15' 1.495(6) . ?
C12 N5 1.511(9) . ?
N5 N5' 0.941(6) . ?
N5 C15' 0.944(6) . ?
N5 C15 1.284(9) . ?
C15 C15' 0.880(8) . ?
C15 N5' 0.975(7) . ?
N5' C15' 1.359(5) . ?

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 C4 91.11(8) . . ?
N3 C6 C11 125.70(15) . . ?
N3 C6 C7 115.67(15) . . ?
C11 C6 C7 118.63(15) . . ?
C7 C8 C9 118.97(17) . . ?
C10 C9 C8 120.82(16) . . ?
C10 C9 N4 120.16(15) . . ?
C8 C9 N4 119.01(16) . . ?
C10 C11 C6 119.77(15) . . ?
C9 C10 C11 120.39(15) . . ?
C8 C7 C6 121.39(16) . . ?
N2 C5 N3 115.98(14) . . ?
N2 C5 S2 127.49(12) . . ?
N3 C5 S2 116.53(12) . . ?
N2 C4 N1 118.85(15) . . ?
N2 C4 S1 131.92(12) . . ?
N1 C4 S1 109.24(12) . . ?
C3 C2 C1 128.23(18) . . ?
C3 C2 S1 110.62(14) . . ?
C1 C2 S1 121.15(15) . . ?
C2 C3 N1 113.61(17) . . ?
C5 N3 C6 132.71(15) . . ?
C5 N2 C4 121.63(14) . . ?
C4 N1 C3 115.42(16) . . ?
O1 N4 O2 122.52(18) . . ?
O1 N4 C9 118.72(17) . . ?
O2 N4 C9 118.76(17) . . ?
C15 O3 C15' 40.3(3) . . ?
N5' C14 C15 37.2(2) . . ?
N5' C13 N5 36.3(2) . . ?
C15' C12 N5 36.6(2) . . ?
N5' N5 C15' 92.3(6) . . ?
N5' N5 C15 49.0(5) . . ?
C15' N5 C15 43.3(4) . . ?
N5' N5 C12 163.0(8) . . ?
C15' N5 C12 70.8(7) . . ?
C15 N5 C12 114.1(9) . . ?
N5' N5 C13 68.9(6) . . ?
C15' N5 C13 161.0(9) . . ?
C15 N5 C13 117.9(9) . . ?
C12 N5 C13 127.9(4) . . ?
C15' C15 N5' 94.1(8) . . ?
C15' C15 O3 69.9(9) . . ?
N5' C15 O3 164.0(11) . . ?
C15' C15 N5 47.3(5) . . ?
N5' C15 N5 46.8(4) . . ?
O3 C15 N5 117.2(11) . . ?
C15' C15 C14 159.9(9) . . ?
N5' C15 C14 65.9(8) . . ?
O3 C15 C14 130.1(6) . . ?
N5 C15 C14 112.7(9) . . ?
N5 N5' C15 84.2(7) . . ?
N5 N5' C15' 44.0(4) . . ?
C15 N5' C15' 40.2(5) . . ?
N5 N5' C14 161.1(7) . . ?
C15 N5' C14 77.0(8) . . ?
C15' N5' C14 117.2(5) . . ?
N5 N5' C13 74.8(6) . . ?
C15 N5' C13 158.9(9) . . ?
C15' N5' C13 118.7(5) . . ?
C14 N5' C13 124.1(3) . . ?
C15 C15' N5 89.4(7) . . ?
C15 C15' O3 69.8(8) . . ?
N5 C15' O3 159.2(8) . . ?
C15 C15' N5' 45.7(5) . . ?
N5 C15' N5' 43.8(4) . . ?
O3 C15' N5' 115.5(6) . . ?
C15 C15' C12 162.0(9) . . ?
N5 C15' C12 72.6(7) . . ?
O3 C15' C12 128.2(4) . . ?
N5' C15' C12 116.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1445145'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 N4 O4 S'
_chemical_formula_weight         296.31

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.557(2)
_cell_length_b                   8.595(2)
_cell_length_c                   12.225(3)
_cell_angle_alpha                92.35(2)
_cell_angle_beta                 91.90(2)
_cell_angle_gamma                98.16(2)
_cell_volume                     680.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    521
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      13.66

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   multi-scan

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7334
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_sigmaI/netI    0.2294
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2399
_reflns_number_gt                1122
_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)+(0.0090P)²+5.5000P] 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         2399
_refine_ls_number_parameters     190
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.2901
_refine_ls_R_factor_gt           0.1164
_refine_ls_wR_factor_ref         0.3261
_refine_ls_wR_factor_gt          0.2735
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.002

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 0.8226(6) 0.3967(5) -0.2170(3) 0.0749(14) Uani 1 1 d . . .
O1 O 0.7821(13) 0.2069(10) -0.0372(6) 0.064(3) Uani 1 1 d . . .
O2 O 0.791(2) -0.2302(15) 0.4894(10) 0.127(5) Uani 1 1 d . . .
O3 O 0.505(2) -0.258(2) 0.3989(9) 0.174(7) Uani 1 1 d . . .
N1 N 1.2089(16) 0.4986(13) -0.1997(8) 0.064(3) Uani 1 1 d . . .
N2 N 1.0995(15) 0.3419(12) -0.0550(8) 0.057(3) Uani 1 1 d . . .
H2 H 1.2210 0.3659 -0.0250 0.068 Uiso 1 1 calc R . .
N3 N 1.0409(14) 0.1823(12) 0.0864(8) 0.057(3) Uani 1 1 d . . .
H3A H 1.1705 0.2118 0.0996 0.069 Uiso 1 1 calc R . .
N4 N 0.690(3) -0.2060(17) 0.4109(11) 0.106(5) Uani 1 1 d . . .
C2 C 1.138(3) 0.5554(16) -0.2983(11) 0.074(4) Uani 1 1 d . . .
C3 C 0.935(2) 0.5119(17) -0.3175(11) 0.084(5) Uani 1 1 d . . .
H3 H 0.8621 0.5406 -0.3783 0.101 Uiso 1 1 calc R . .
C4 C 1.0586(19) 0.4116(14) -0.1524(10) 0.050(3) Uani 1 1 d . . .
C5 C 0.962(2) 0.2385(15) -0.0033(10) 0.049(3) Uani 1 1 d . . .
C6 C 0.9430(19) 0.0825(15) 0.1619(10) 0.058(4) Uani 1 1 d D . .
C7 C 1.066(2) 0.0520(16) 0.2538(10) 0.070(4) Uani 1 1 d D . .
H7 H 1.2031 0.0983 0.2610 0.083 Uiso 1 1 calc R . .
C8 C 0.984(2) -0.0462(17) 0.3330(11) 0.078(4) Uani 1 1 d D . .
H8 H 1.0647 -0.0692 0.3924 0.093 Uiso 1 1 calc R . .
C10 C 0.6496(19) -0.0836(15) 0.2305(10) 0.066(4) Uani 1 1 d D . .
H10 H 0.5109 -0.1263 0.2254 0.079 Uiso 1 1 calc R . .
C11 C 0.7370(18) 0.0077(14) 0.1487(10) 0.060(4) Uani 1 1 d D . .
H11 H 0.6601 0.0197 0.0851 0.072 Uiso 1 1 calc R . .
O4 O 0.4624(16) 0.3235(15) 0.0748(9) 0.075(3) Uani 1 1 d D . .
C9 C 0.775(2) -0.1100(17) 0.3211(11) 0.077(4) Uani 1 1 d D . .
C1 C 1.288(2) 0.6499(17) -0.3652(10) 0.089(5) Uani 1 1 d . . .
H1A H 1.4014 0.5931 -0.3794 0.133 Uiso 1 1 calc R . .
H1B H 1.3391 0.7478 -0.3263 0.133 Uiso 1 1 calc R . .
H1C H 1.2225 0.6703 -0.4333 0.133 Uiso 1 1 calc R . .
H1P H 0.518(16) 0.261(10) 0.033(7) 0.05(4) Uiso 1 1 d D . .
H4Q H 0.578(16) 0.386(18) 0.078(15) 0.16(9) Uiso 1 1 d 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 C4 1.700(12) . ?
S1 C3 1.727(13) . ?
O1 C5 1.228(12) . ?
O2 N4 1.192(15) . ?
O3 N4 1.233(15) . ?
N1 C4 1.314(13) . ?
N1 C2 1.408(14) . ?
N2 C5 1.362(13) . ?
N2 C4 1.390(14) . ?
N2 H2 0.8600 . ?
N3 C5 1.333(13) . ?
N3 C6 1.396(14) . ?
N3 H3A 0.8600 . ?
N4 C9 1.478(17) . ?
C2 C3 1.345(17) . ?
C2 C1 1.475(17) . ?
C3 H3 0.9300 . ?
C6 C11 1.412(12) . ?
C6 C7 1.416(12) . ?
C7 C8 1.383(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.402(13) . ?
C8 H8 0.9300 . ?
C10 C11 1.385(12) . ?
C10 C9 1.402(13) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
O4 H1P 0.85(2) . ?
O4 H4Q 0.86(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C4 S1 C3 88.4(7) . . ?
C4 N1 C2 111.1(11) . . ?
C5 N2 C4 125.2(10) . . ?
C5 N2 H2 117.4 . . ?
C4 N2 H2 117.4 . . ?
C5 N3 C6 129.3(11) . . ?
C5 N3 H3A 115.3 . . ?
C6 N3 H3A 115.3 . . ?
O2 N4 O3 122.5(15) . . ?
O2 N4 C9 122.6(15) . . ?
O3 N4 C9 114.9(15) . . ?
C3 C2 N1 112.2(13) . . ?
C3 C2 C1 129.2(13) . . ?
N1 C2 C1 118.6(13) . . ?
C2 C3 S1 112.7(11) . . ?
C2 C3 H3 123.7 . . ?
S1 C3 H3 123.7 . . ?
N1 C4 N2 119.6(11) . . ?
N1 C4 S1 115.6(9) . . ?
N2 C4 S1 124.8(9) . . ?
O1 C5 N3 125.0(12) . . ?
O1 C5 N2 121.0(12) . . ?
N3 C5 N2 113.9(12) . . ?
N3 C6 C11 124.0(11) . . ?
N3 C6 C7 116.1(11) . . ?
C11 C6 C7 119.9(11) . . ?
C8 C7 C6 120.5(12) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 118.1(12) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
C11 C10 C9 118.5(12) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C6 120.0(11) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
H1P O4 H4Q 88(10) . . ?
C8 C9 C10 122.8(12) . . ?
C8 C9 N4 116.4(13) . . ?
C10 C9 N4 120.8(13) . . ?
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 . . ?

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
C4 N1 C2 C3 2.3(17) . . . . ?
C4 N1 C2 C1 -177.4(12) . . . . ?
N1 C2 C3 S1 -1.1(17) . . . . ?
C1 C2 C3 S1 178.5(12) . . . . ?
C4 S1 C3 C2 -0.2(12) . . . . ?
C2 N1 C4 N2 178.5(11) . . . . ?
C2 N1 C4 S1 -2.5(14) . . . . ?
C5 N2 C4 N1 -173.9(12) . . . . ?
C5 N2 C4 S1 7.3(17) . . . . ?
C3 S1 C4 N1 1.6(10) . . . . ?
C3 S1 C4 N2 -179.5(11) . . . . ?
C6 N3 C5 O1 -2(2) . . . . ?
C6 N3 C5 N2 176.0(11) . . . . ?
C4 N2 C5 O1 -5.0(18) . . . . ?
C4 N2 C5 N3 177.1(11) . . . . ?
C5 N3 C6 C11 7(2) . . . . ?
C5 N3 C6 C7 -175.7(12) . . . . ?
N3 C6 C7 C8 -179.6(13) . . . . ?
C11 C6 C7 C8 -2(2) . . . . ?
C6 C7 C8 C9 -2(2) . . . . ?
C9 C10 C11 C6 -5(2) . . . . ?
N3 C6 C11 C10 -176.9(12) . . . . ?
C7 C6 C11 C10 6.1(19) . . . . ?
C7 C8 C9 C10 3(2) . . . . ?
C7 C8 C9 N4 -176.2(13) . . . . ?
C11 C10 C9 C8 1(2) . . . . ?
C11 C10 C9 N4 179.8(13) . . . . ?
O2 N4 C9 C8 -1(2) . . . . ?
O3 N4 C9 C8 178.9(16) . . . . ?
O2 N4 C9 C10 -179.6(16) . . . . ?
O3 N4 C9 C10 0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.081


####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1445146'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N7 O5 S'
_chemical_formula_weight         511.56

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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4079(8)
_cell_length_b                   10.8878(11)
_cell_length_c                   13.9669(14)
_cell_angle_alpha                86.117(6)
_cell_angle_beta                 85.722(6)
_cell_angle_gamma                68.541(5)
_cell_volume                     1185.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    920
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      17.76

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             543
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   multi-scan

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6964
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.1054
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4100
_reflns_number_gt                1507
_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)+(0.0000P)²+0.4000P] 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         4100
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.002
_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 0.19546(14) 1.28439(10) -0.00324(7) 0.0621(4) Uani 1 1 d . . .
C9 C 0.5064(5) 0.9300(4) -0.2566(3) 0.0490(12) Uani 1 1 d . . .
C12 C 0.6344(6) 1.0260(4) -0.4195(3) 0.0503(12) Uani 1 1 d . . .
C14 C 0.4329(5) 1.0625(4) -0.2847(3) 0.0566(12) Uani 1 1 d . . .
H14 H 0.3411 1.1190 -0.2487 0.068 Uiso 1 1 calc R . .
C6 C -0.0159(5) 1.3994(4) 0.1572(3) 0.0537(12) Uani 1 1 d . . .
H6 H -0.0140 1.4828 0.1395 0.064 Uiso 1 1 calc R . .
C4 C 0.0716(5) 1.1647(4) 0.1297(3) 0.0480(12) Uani 1 1 d . . .
C3 C -0.0217(5) 1.1478(4) 0.2138(3) 0.0576(13) Uani 1 1 d . . .
H3 H -0.0229 1.0646 0.2327 0.069 Uiso 1 1 calc R . .
C10 C 0.6434(5) 0.8472(4) -0.3116(3) 0.0628(13) Uani 1 1 d . . .
H10 H 0.6927 0.7583 -0.2931 0.075 Uiso 1 1 calc R . .
C1 C -0.1081(5) 1.3775(5) 0.2391(3) 0.0512(12) Uani 1 1 d . . .
C11 C 0.7067(5) 0.8959(4) -0.3930(3) 0.0619(13) Uani 1 1 d . . .
H11 H 0.7982 0.8401 -0.4297 0.074 Uiso 1 1 calc R . .
C5 C 0.0729(5) 1.2910(4) 0.1036(3) 0.0478(12) Uani 1 1 d . . .
C2 C -0.1118(5) 1.2552(5) 0.2684(3) 0.0548(12) Uani 1 1 d . . .
H2 H -0.1741 1.2450 0.3242 0.066 Uiso 1 1 calc R . .
C13 C 0.4977(5) 1.1098(4) -0.3669(3) 0.0627(13) Uani 1 1 d . . .
H13 H 0.4488 1.1984 -0.3867 0.075 Uiso 1 1 calc R . .
C7 C 0.2313(5) 1.1138(4) -0.0067(3) 0.0526(12) Uani 1 1 d . . .
N2 N 0.3229(4) 1.0550(3) -0.0846(2) 0.0579(11) Uani 1 1 d . . .
N3 N 0.4453(4) 0.8698(4) -0.1766(3) 0.0547(11) Uani 1 1 d . . .
N1 N 0.1612(4) 1.0662(3) 0.0674(2) 0.0563(10) Uani 1 1 d . . .
N4 N 0.7043(5) 1.0793(4) -0.5042(3) 0.0684(12) Uani 1 1 d . . .
O2 O 0.6448(4) 1.1982(3) -0.5240(2) 0.0957(12) Uani 1 1 d . . .
O1 O 0.8201(4) 1.0043(3) -0.5525(2) 0.1056(13) Uani 1 1 d . . .
N7 N 0.3491(4) 0.6283(4) 0.2364(2) 0.0557(10) Uani 1 1 d . . .
C21 C 0.1485(5) 0.5186(4) 0.3940(3) 0.0715(14) Uani 1 1 d . . .
H21A H 0.1290 0.4728 0.4531 0.086 Uiso 1 1 calc R . .
H21B H 0.1096 0.4839 0.3420 0.086 Uiso 1 1 calc R . .
C22 C 0.3381(5) 0.4878(4) 0.3775(3) 0.0616(13) Uani 1 1 d . . .
H22A H 0.3708 0.5456 0.4151 0.074 Uiso 1 1 calc R . .
H22B H 0.3990 0.3976 0.4001 0.074 Uiso 1 1 calc R . .
C18 C 0.2371(6) 0.7456(4) 0.2876(3) 0.0747(14) Uani 1 1 d . . .
H18A H 0.2312 0.8242 0.2487 0.090 Uiso 1 1 calc R . .
H18B H 0.2876 0.7487 0.3472 0.090 Uiso 1 1 calc R . .
C20 C 0.0403(5) 0.6655(4) 0.4006(3) 0.0788(14) Uani 1 1 d . . .
H20A H -0.0789 0.6756 0.4124 0.095 Uiso 1 1 calc R . .
H20B H 0.0740 0.6994 0.4550 0.095 Uiso 1 1 calc R . .
C19 C 0.0576(6) 0.7475(4) 0.3103(3) 0.0851(16) Uani 1 1 d . . .
H19A H 0.0218 0.7144 0.2562 0.102 Uiso 1 1 calc R . .
H19B H -0.0192 0.8381 0.3180 0.102 Uiso 1 1 calc R . .
C16 C 0.2894(5) 0.6577(4) 0.0622(3) 0.0585(12) Uani 1 1 d . . .
H16A H 0.1755 0.7169 0.0817 0.070 Uiso 1 1 calc R . .
H16B H 0.2851 0.5707 0.0559 0.070 Uiso 1 1 calc R . .
C17 C 0.4124(5) 0.6507(4) 0.1378(3) 0.0592(13) Uani 1 1 d . . .
H17A H 0.5204 0.5797 0.1237 0.071 Uiso 1 1 calc R . .
H17B H 0.4338 0.7326 0.1344 0.071 Uiso 1 1 calc R . .
C15 C 0.3463(5) 0.7072(4) -0.0346(3) 0.0581(12) Uani 1 1 d . . .
H15A H 0.4677 0.6604 -0.0480 0.070 Uiso 1 1 calc R . .
H15B H 0.2847 0.6916 -0.0856 0.070 Uiso 1 1 calc R . .
N5 N -0.2098(5) 1.4928(4) 0.2955(3) 0.0630(12) Uani 1 1 d . . .
O3 O -0.2351(4) 1.6041(3) 0.2585(2) 0.0828(11) Uani 1 1 d . . .
O4 O -0.2659(4) 1.4733(3) 0.3763(2) 0.0856(11) Uani 1 1 d . . .
C8 C 0.3569(5) 0.9274(5) -0.0951(3) 0.0512(12) Uani 1 1 d . . .
N6 N 0.3104(4) 0.8490(4) -0.0302(3) 0.0555(11) Uani 1 1 d . . .
O5 O 0.4710(4) 0.4086(3) 0.22539(19) 0.0789(10) Uani 1 1 d . . .
C23 C 0.3918(5) 0.5039(5) 0.2737(3) 0.0538(13) Uani 1 1 d . . .
H3A H 0.471(3) 0.786(3) -0.1802(19) 0.022(11) Uiso 1 1 d . . .
H6A H 0.251(5) 0.892(4) 0.024(3) 0.086(16) 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 C5 1.739(4) . ?
S1 C7 1.772(4) . ?
C9 C14 1.388(4) . ?
C9 C10 1.389(4) . ?
C9 N3 1.415(4) . ?
C12 C11 1.359(4) . ?
C12 C13 1.375(4) . ?
C12 N4 1.461(5) . ?
C14 C13 1.383(4) . ?
C6 C5 1.379(4) . ?
C6 C1 1.390(4) . ?
C4 N1 1.383(4) . ?
C4 C3 1.402(4) . ?
C4 C5 1.402(4) . ?
C3 C2 1.382(4) . ?
C10 C11 1.376(4) . ?
C1 C2 1.377(4) . ?
C1 N5 1.475(5) . ?
C7 N1 1.322(4) . ?
C7 N2 1.340(4) . ?
N2 C8 1.328(4) . ?
N3 C8 1.369(4) . ?
N4 O1 1.211(4) . ?
N4 O2 1.225(4) . ?
N7 C23 1.346(4) . ?
N7 C18 1.475(4) . ?
N7 C17 1.476(4) . ?
C21 C22 1.507(4) . ?
C21 C20 1.529(4) . ?
C22 C23 1.503(4) . ?
C18 C19 1.512(5) . ?
C20 C19 1.525(4) . ?
C16 C17 1.511(4) . ?
C16 C15 1.531(4) . ?
C15 N6 1.466(4) . ?
N5 O4 1.226(4) . ?
N5 O3 1.234(4) . ?
C8 N6 1.337(4) . ?
O5 C23 1.224(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C7 89.2(2) . . ?
C14 C9 C10 119.5(4) . . ?
C14 C9 N3 124.1(4) . . ?
C10 C9 N3 116.4(4) . . ?
C11 C12 C13 121.2(4) . . ?
C11 C12 N4 119.9(4) . . ?
C13 C12 N4 118.9(4) . . ?
C13 C14 C9 119.3(4) . . ?
C5 C6 C1 116.5(4) . . ?
N1 C4 C3 125.1(4) . . ?
N1 C4 C5 116.0(4) . . ?
C3 C4 C5 118.9(4) . . ?
C2 C3 C4 119.8(4) . . ?
C11 C10 C9 120.5(4) . . ?
C2 C1 C6 123.4(4) . . ?
C2 C1 N5 119.0(4) . . ?
C6 C1 N5 117.6(4) . . ?
C12 C11 C10 119.5(4) . . ?
C6 C5 C4 122.3(4) . . ?
C6 C5 S1 128.4(4) . . ?
C4 C5 S1 109.4(3) . . ?
C1 C2 C3 119.2(4) . . ?
C12 C13 C14 120.0(4) . . ?
N1 C7 N2 130.7(4) . . ?
N1 C7 S1 114.6(3) . . ?
N2 C7 S1 114.7(3) . . ?
C8 N2 C7 119.9(4) . . ?
C8 N3 C9 128.2(4) . . ?
C7 N1 C4 110.8(4) . . ?
O1 N4 O2 122.0(4) . . ?
O1 N4 C12 118.7(4) . . ?
O2 N4 C12 119.3(4) . . ?
C23 N7 C18 123.6(3) . . ?
C23 N7 C17 119.3(3) . . ?
C18 N7 C17 117.1(3) . . ?
C22 C21 C20 114.8(3) . . ?
C23 C22 C21 113.2(3) . . ?
N7 C18 C19 113.4(3) . . ?
C19 C20 C21 113.3(3) . . ?
C18 C19 C20 113.8(4) . . ?
C17 C16 C15 110.4(3) . . ?
N7 C17 C16 113.4(3) . . ?
N6 C15 C16 108.4(3) . . ?
O4 N5 O3 123.4(4) . . ?
O4 N5 C1 118.4(4) . . ?
O3 N5 C1 118.2(4) . . ?
N2 C8 N6 124.2(4) . . ?
N2 C8 N3 119.2(4) . . ?
N6 C8 N3 116.6(4) . . ?
C8 N6 C15 127.8(4) . . ?
O5 C23 N7 121.4(4) . . ?
O5 C23 C22 121.7(4) . . ?
N7 C23 C22 116.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046





