# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ddv2rm
_database_code_depnum_ccdc_archive 'CCDC 1500511'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
;  
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 F3 N O2, C12 H14 N4 O2 S'
_chemical_formula_sum            'C26 H24 F3 N5 O4 S'
_chemical_formula_weight         559.56

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'
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'
F F 0.0171 0.0103 '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           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_hall  -P2ac2ab

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

_cell_length_a                   15.889(2)
_cell_length_b                   14.854(2)
_cell_length_c                   22.217(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5243.3(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1165
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      20.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .57
_exptl_crystal_size_mid          .27
_exptl_crystal_size_min          .18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2320
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .796
_exptl_absorpt_correction_T_max  .997
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            21212
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4609
_reflns_number_gt                3050
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1301P)²+2.9315P] 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         4585
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.2242
_refine_ls_wR_factor_gt          0.1970
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 1.10541(6) -0.04822(6) 0.19303(4) 0.0428(3) Uani 1 1 d . . .
O2 O 1.05858(18) -0.08270(19) 0.24241(13) 0.0576(8) Uani 1 1 d . . .
O1 O 1.18842(17) -0.08137(19) 0.18179(14) 0.0588(8) Uani 1 1 d . . .
N4 N 0.94852(18) -0.08182(19) 0.06143(14) 0.0402(7) Uani 1 1 d . . .
N3 N 0.92279(19) -0.0242(2) 0.16015(14) 0.0415(8) Uani 1 1 d . . .
N2 N 1.05571(18) -0.0731(2) 0.13032(14) 0.0447(8) Uani 1 1 d . . .
H200 H 1.0853 -0.0977 0.1024 0.054 Uiso 1 1 calc R . .
C1 C 0.9719(2) -0.0588(2) 0.11744(17) 0.0387(9) Uani 1 1 d . . .
C2 C 1.0507(2) 0.2081(3) 0.23273(18) 0.0492(10) Uani 1 1 d . . .
H2 H 1.0092 0.2392 0.2536 0.059 Uiso 1 1 calc R . .
C3 C 1.1089(2) 0.0695(2) 0.19843(15) 0.0383(9) Uani 1 1 d . . .
C4 C 1.1791(3) 0.2071(3) 0.17666(18) 0.0482(10) Uani 1 1 d . . .
H4 H 1.2243 0.2375 0.1595 0.058 Uiso 1 1 calc R . .
C5 C 0.8129(2) -0.0319(3) 0.08837(19) 0.0495(10) Uani 1 1 d . . .
H5 H 0.7570 -0.0210 0.0781 0.059 Uiso 1 1 calc R . .
C6 C 0.8672(2) -0.0688(2) 0.04712(18) 0.0430(9) Uani 1 1 d . . .
C7 C 1.1755(2) 0.1157(3) 0.17270(17) 0.0459(10) Uani 1 1 d . . .
H7 H 1.2177 0.0843 0.1527 0.055 Uiso 1 1 calc R . .
C8 C 1.1164(2) 0.2559(3) 0.20582(16) 0.0433(9) Uani 1 1 d . . .
C9 C 0.8418(2) -0.0109(2) 0.14536(19) 0.0448(10) Uani 1 1 d . . .
N1 N 1.1192(2) 0.3477(2) 0.20879(16) 0.0607(10) Uani 1 1 d . . .
H1A H 1.1603 0.3765 0.1924 0.073 Uiso 1 1 calc R . .
H1B H 1.0799 0.3768 0.2270 0.073 Uiso 1 1 calc R . .
C10 C 1.0463(2) 0.1159(3) 0.22899(18) 0.0467(10) Uani 1 1 d . . .
H10 H 1.0019 0.0849 0.2467 0.056 Uiso 1 1 calc R . .
C11 C 0.7865(3) 0.0274(3) 0.1932(2) 0.0603(12) Uani 1 1 d . . .
H11A H 0.7549 -0.0202 0.2118 0.090 Uiso 1 1 calc R . .
H11B H 0.7484 0.0702 0.1757 0.090 Uiso 1 1 calc R . .
H11C H 0.8205 0.0569 0.2230 0.090 Uiso 1 1 calc R . .
C12 C 0.8400(3) -0.0944(3) -0.0150(2) 0.0649(13) Uani 1 1 d . . .
H12A H 0.8699 -0.0586 -0.0439 0.097 Uiso 1 1 calc R . .
H12B H 0.7806 -0.0840 -0.0193 0.097 Uiso 1 1 calc R . .
H12C H 0.8519 -0.1569 -0.0218 0.097 Uiso 1 1 calc R . .
O3 O 0.15236(17) 0.8665(2) 1.02857(13) 0.0568(8) Uani 1 1 d . . .
O4 O 0.04013(18) 0.8565(2) 0.96971(13) 0.0615(8) Uani 1 1 d . . .
H4A H 0.0167 0.8739 1.0005 0.092 Uiso 1 1 calc R . .
N5 N 0.3010(2) 0.8351(3) 0.97719(15) 0.0578(10) Uani 1 1 d . . .
H5A H 0.2704 0.8488 1.0078 0.069 Uiso 1 1 calc R . .
C13 C 0.2568(2) 0.8007(2) 0.92958(17) 0.0442(9) Uani 1 1 d . . .
C14 C 0.1679(2) 0.8082(2) 0.92914(17) 0.0426(9) Uani 1 1 d . . .
C15 C 0.1205(2) 0.8460(2) 0.98009(18) 0.0446(9) Uani 1 1 d . . .
C16 C 0.4162(3) 0.8606(3) 1.0436(2) 0.0596(12) Uani 1 1 d . . .
H16 H 0.3790 0.8532 1.0755 0.072 Uiso 1 1 calc R . .
C17 C 0.2485(3) 0.7244(3) 0.83380(19) 0.0572(12) Uani 1 1 d . . .
H17 H 0.2756 0.6948 0.8024 0.069 Uiso 1 1 calc R . .
C18 C 0.2954(3) 0.7568(3) 0.88107(18) 0.0501(10) Uani 1 1 d . . .
H18 H 0.3536 0.7496 0.8808 0.060 Uiso 1 1 calc R . .
C19 C 0.3869(2) 0.8519(3) 0.98504(19) 0.0510(10) Uani 1 1 d . . .
C20 C 0.4437(3) 0.8641(3) 0.9378(2) 0.0573(11) Uani 1 1 d . . .
H20 H 0.4252 0.8614 0.8981 0.069 Uiso 1 1 calc R . .
C21 C 0.1230(3) 0.7758(3) 0.87935(18) 0.0512(10) Uani 1 1 d . . .
H21 H 0.0648 0.7823 0.8784 0.061 Uiso 1 1 calc R . .
C22 C 0.4990(3) 0.8799(3) 1.0551(2) 0.0660(13) Uani 1 1 d . . .
H22 H 0.5171 0.8870 1.0946 0.079 Uiso 1 1 calc R . .
C23 C 0.5274(3) 0.8803(3) 0.9503(2) 0.0621(12) Uani 1 1 d . . .
C24 C 0.1629(3) 0.7346(3) 0.8318(2) 0.0631(12) Uani 1 1 d . . .
H24 H 0.1322 0.7141 0.7989 0.076 Uiso 1 1 calc R . .
C25 C 0.5557(3) 0.8889(3) 1.0084(2) 0.0688(13) Uani 1 1 d . . .
H25 H 0.6121 0.9006 1.0162 0.083 Uiso 1 1 calc R . .
F3 F 0.5604(3) 0.9414(4) 0.85633(19) 0.1482(18) Uani 1 1 d . . .
F1 F 0.6556(2) 0.9265(6) 0.9119(2) 0.231(4) Uani 1 1 d . . .
C26 C 0.5867(3) 0.8868(6) 0.8997(3) 0.095(2) Uani 1 1 d . . .
F2 F 0.5995(4) 0.8166(4) 0.8709(3) 0.238(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.421(3) . ?
S1 O1 1.430(3) . ?
S1 N2 1.643(3) . ?
S1 C3 1.754(4) . ?
N4 C1 1.343(5) . ?
N4 C6 1.344(5) . ?
N3 C1 1.332(4) . ?
N3 C9 1.342(5) . ?
N2 C1 1.378(4) . ?
N2 H200 0.8600 . ?
C2 C10 1.373(5) . ?
C2 C8 1.397(5) . ?
C2 H2 0.9300 . ?
C3 C7 1.384(5) . ?
C3 C10 1.388(5) . ?
C4 C7 1.362(5) . ?
C4 C8 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(5) . ?
C5 C9 1.383(6) . ?
C5 H5 0.9300 . ?
C6 C12 1.496(6) . ?
C7 H7 0.9300 . ?
C8 N1 1.367(5) . ?
C9 C11 1.493(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O3 C15 1.228(4) . ?
O4 C15 1.307(5) . ?
O4 H4A 0.8200 . ?
N5 C13 1.369(5) . ?
N5 C19 1.399(5) . ?
N5 H5A 0.8600 . ?
C13 C18 1.401(5) . ?
C13 C14 1.416(5) . ?
C14 C21 1.402(5) . ?
C14 C15 1.471(5) . ?
C16 C22 1.371(6) . ?
C16 C19 1.387(6) . ?
C16 H16 0.9300 . ?
C17 C24 1.370(6) . ?
C17 C18 1.375(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.396(6) . ?
C20 C23 1.379(6) . ?
C20 H20 0.9300 . ?
C21 C24 1.375(6) . ?
C21 H21 0.9300 . ?
C22 C25 1.380(7) . ?
C22 H22 0.9300 . ?
C23 C25 1.374(7) . ?
C23 C26 1.471(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
F3 C26 1.328(7) . ?
F1 C26 1.273(8) . ?
C26 F2 1.241(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.58(18) . . ?
O2 S1 N2 108.77(17) . . ?
O1 S1 N2 102.58(16) . . ?
O2 S1 C3 108.86(17) . . ?
O1 S1 C3 109.03(17) . . ?
N2 S1 C3 107.30(16) . . ?
C1 N4 C6 116.7(3) . . ?
C1 N3 C9 116.4(3) . . ?
C1 N2 S1 127.3(3) . . ?
C1 N2 H200 116.4 . . ?
S1 N2 H200 116.4 . . ?
N3 C1 N4 126.6(3) . . ?
N3 C1 N2 118.5(3) . . ?
N4 C1 N2 114.9(3) . . ?
C10 C2 C8 121.3(4) . . ?
C10 C2 H2 119.4 . . ?
C8 C2 H2 119.4 . . ?
C7 C3 C10 120.3(4) . . ?
C7 C3 S1 119.4(3) . . ?
C10 C3 S1 120.4(3) . . ?
C7 C4 C8 121.3(4) . . ?
C7 C4 H4 119.4 . . ?
C8 C4 H4 119.4 . . ?
C6 C5 C9 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C9 C5 H5 120.3 . . ?
N4 C6 C5 120.3(4) . . ?
N4 C6 C12 117.4(4) . . ?
C5 C6 C12 122.4(4) . . ?
C4 C7 C3 119.9(4) . . ?
C4 C7 H7 120.0 . . ?
C3 C7 H7 120.0 . . ?
N1 C8 C4 121.3(4) . . ?
N1 C8 C2 120.7(4) . . ?
C4 C8 C2 118.0(4) . . ?
N3 C9 C5 120.7(4) . . ?
N3 C9 C11 116.5(4) . . ?
C5 C9 C11 122.8(4) . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C2 C10 C3 119.2(4) . . ?
C2 C10 H10 120.4 . . ?
C3 C10 H10 120.4 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 O4 H4A 109.5 . . ?
C13 N5 C19 131.6(3) . . ?
C13 N5 H5A 114.2 . . ?
C19 N5 H5A 114.2 . . ?
N5 C13 C18 122.9(4) . . ?
N5 C13 C14 119.2(3) . . ?
C18 C13 C14 117.9(4) . . ?
C21 C14 C13 119.0(3) . . ?
C21 C14 C15 118.5(4) . . ?
C13 C14 C15 122.4(4) . . ?
O3 C15 O4 121.9(4) . . ?
O3 C15 C14 123.9(4) . . ?
O4 C15 C14 114.2(4) . . ?
C22 C16 C19 121.1(4) . . ?
C22 C16 H16 119.4 . . ?
C19 C16 H16 119.4 . . ?
C24 C17 C18 121.6(4) . . ?
C24 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 120.9(4) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C16 C19 C20 118.4(4) . . ?
C16 C19 N5 117.4(4) . . ?
C20 C19 N5 124.1(4) . . ?
C23 C20 C19 119.6(4) . . ?
C23 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C24 C21 C14 121.6(4) . . ?
C24 C21 H21 119.2 . . ?
C14 C21 H21 119.2 . . ?
C16 C22 C25 120.4(5) . . ?
C16 C22 H22 119.8 . . ?
C25 C22 H22 119.8 . . ?
C25 C23 C20 121.4(4) . . ?
C25 C23 C26 120.2(5) . . ?
C20 C23 C26 118.4(5) . . ?
C17 C24 C21 118.8(4) . . ?
C17 C24 H24 120.6 . . ?
C21 C24 H24 120.6 . . ?
C23 C25 C22 118.9(4) . . ?
C23 C25 H25 120.5 . . ?
C22 C25 H25 120.5 . . ?
F2 C26 F1 111.1(6) . . ?
F2 C26 F3 101.0(6) . . ?
F1 C26 F3 98.2(7) . . ?
F2 C26 C23 116.4(6) . . ?
F1 C26 C23 114.8(6) . . ?
F3 C26 C23 113.1(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
O2 S1 N2 C1 49.9(4) . . . . ?
O1 S1 N2 C1 177.5(3) . . . . ?
C3 S1 N2 C1 -67.7(4) . . . . ?
C9 N3 C1 N4 -0.2(5) . . . . ?
C9 N3 C1 N2 179.5(3) . . . . ?
C6 N4 C1 N3 -0.2(5) . . . . ?
C6 N4 C1 N2 -179.9(3) . . . . ?
S1 N2 C1 N3 -2.7(5) . . . . ?
S1 N2 C1 N4 177.0(3) . . . . ?
O2 S1 C3 C7 153.6(3) . . . . ?
O1 S1 C3 C7 21.6(3) . . . . ?
N2 S1 C3 C7 -88.8(3) . . . . ?
O2 S1 C3 C10 -25.4(3) . . . . ?
O1 S1 C3 C10 -157.4(3) . . . . ?
N2 S1 C3 C10 92.2(3) . . . . ?
C1 N4 C6 C5 1.4(5) . . . . ?
C1 N4 C6 C12 -179.8(3) . . . . ?
C9 C5 C6 N4 -2.1(6) . . . . ?
C9 C5 C6 C12 179.1(4) . . . . ?
C8 C4 C7 C3 -0.5(6) . . . . ?
C10 C3 C7 C4 -0.9(6) . . . . ?
S1 C3 C7 C4 -179.9(3) . . . . ?
C7 C4 C8 N1 -178.7(4) . . . . ?
C7 C4 C8 C2 2.0(6) . . . . ?
C10 C2 C8 N1 178.6(4) . . . . ?
C10 C2 C8 C4 -2.1(6) . . . . ?
C1 N3 C9 C5 -0.6(5) . . . . ?
C1 N3 C9 C11 179.7(3) . . . . ?
C6 C5 C9 N3 1.7(6) . . . . ?
C6 C5 C9 C11 -178.6(4) . . . . ?
C8 C2 C10 C3 0.7(6) . . . . ?
C7 C3 C10 C2 0.8(6) . . . . ?
S1 C3 C10 C2 179.8(3) . . . . ?
C19 N5 C13 C18 14.0(7) . . . . ?
C19 N5 C13 C14 -166.9(4) . . . . ?
N5 C13 C14 C21 177.8(4) . . . . ?
C18 C13 C14 C21 -3.1(5) . . . . ?
N5 C13 C14 C15 -4.5(6) . . . . ?
C18 C13 C14 C15 174.7(3) . . . . ?
C21 C14 C15 O3 171.1(4) . . . . ?
C13 C14 C15 O3 -6.6(6) . . . . ?
C21 C14 C15 O4 -8.9(5) . . . . ?
C13 C14 C15 O4 173.3(3) . . . . ?
C24 C17 C18 C13 0.9(6) . . . . ?
N5 C13 C18 C17 -179.1(4) . . . . ?
C14 C13 C18 C17 1.7(6) . . . . ?
C22 C16 C19 C20 -0.6(6) . . . . ?
C22 C16 C19 N5 -178.0(4) . . . . ?
C13 N5 C19 C16 -160.5(4) . . . . ?
C13 N5 C19 C20 22.3(7) . . . . ?
C16 C19 C20 C23 2.9(6) . . . . ?
N5 C19 C20 C23 -179.9(4) . . . . ?
C13 C14 C21 C24 1.9(6) . . . . ?
C15 C14 C21 C24 -175.9(4) . . . . ?
C19 C16 C22 C25 -1.6(7) . . . . ?
C19 C20 C23 C25 -3.1(7) . . . . ?
C19 C20 C23 C26 175.9(5) . . . . ?
C18 C17 C24 C21 -2.1(7) . . . . ?
C14 C21 C24 C17 0.7(7) . . . . ?
C20 C23 C25 C22 0.8(7) . . . . ?
C26 C23 C25 C22 -178.1(5) . . . . ?
C16 C22 C25 C23 1.5(7) . . . . ?
C25 C23 C26 F2 111.7(7) . . . . ?
C20 C23 C26 F2 -67.3(9) . . . . ?
C25 C23 C26 F1 -20.3(10) . . . . ?
C20 C23 C26 F1 160.7(7) . . . . ?
C25 C23 C26 F3 -132.0(6) . . . . ?
C20 C23 C26 F3 49.0(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_sf4mm
_database_code_depnum_ccdc_archive 'CCDC 1500513'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
;  
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N4 O2 S, C5 H7 N2'
_chemical_formula_sum            'C17 H20 N6 O2 S'
_chemical_formula_weight         372.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_hall  'P 2yb'

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

_cell_length_a                   8.0233(13)
_cell_length_b                   14.923(3)
_cell_length_c                   15.703(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.694(4)
_cell_angle_gamma                90.00
_cell_volume                     1863.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1236
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      21.81

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .56
_exptl_crystal_size_mid          .37
_exptl_crystal_size_min          .17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .783
_exptl_absorpt_correction_T_max  .989
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            8048
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0830
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3950
_reflns_number_gt                3156
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0341P)²+0.2401P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(10)
_refine_ls_number_reflns         3950
_refine_ls_number_parameters     473
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.37330(16) 0.87754(8) 0.60271(7) 0.0422(3) Uani 1 1 d . . .
S2 S 0.81452(15) 0.90100(7) 0.06870(7) 0.0376(3) Uani 1 1 d . . .
O4 O 0.9200(4) 0.8762(2) 0.00563(19) 0.0466(8) Uani 1 1 d . . .
C1 C 0.4751(6) 0.8787(4) 0.0699(3) 0.0428(11) Uani 1 1 d . . .
H1 H 0.4804 0.9293 0.1047 0.051 Uiso 1 1 calc R . .
N3 N 0.4854(5) 0.9992(3) 0.7382(2) 0.0420(10) Uani 1 1 d . . .
C2 C -0.0905(6) 0.8846(4) 0.6717(3) 0.0474(12) Uani 1 1 d . . .
H2 H -0.1987 0.8966 0.6450 0.057 Uiso 1 1 calc R . .
C3 C 0.2036(6) 0.8726(3) 0.6635(3) 0.0389(11) Uani 1 1 d . . .
C4 C 0.4786(6) 1.0318(3) 0.6590(3) 0.0384(11) Uani 1 1 d . . .
N1 N 0.4231(5) 0.9787(3) 0.5887(2) 0.0415(10) Uani 1 1 d . . .
C5 C 0.0425(6) 0.8893(3) 0.6251(3) 0.0437(12) Uani 1 1 d . . .
H5 H 0.0233 0.9040 0.5671 0.052 Uiso 1 1 calc R . .
C6 C -0.0653(6) 0.8621(3) 0.7577(3) 0.0421(12) Uani 1 1 d . . .
N5 N 0.9113(5) 0.7170(3) 0.1270(3) 0.0438(10) Uani 1 1 d . . .
O2 O 0.3075(5) 0.8463(2) 0.5181(2) 0.0542(10) Uani 1 1 d . . .
O1 O 0.5065(4) 0.8236(2) 0.6470(2) 0.0549(10) Uani 1 1 d . . .
N8 N -0.1987(6) 0.8533(3) 0.8048(3) 0.0611(13) Uani 1 1 d . . .
H8A H -0.2999 0.8619 0.7804 0.073 Uiso 1 1 calc R . .
H8B H -0.1802 0.8393 0.8583 0.073 Uiso 1 1 calc R . .
O3 O 0.7861(4) 0.9963(2) 0.0763(2) 0.0498(9) Uani 1 1 d . . .
N2 N 0.5190(5) 1.1154(3) 0.6383(2) 0.0469(11) Uani 1 1 d . . .
C7 C 0.3151(6) 0.7558(3) 0.0012(3) 0.0408(12) Uani 1 1 d . . .
N6 N 0.9070(5) 0.7668(3) 0.2705(3) 0.0501(11) Uani 1 1 d . . .
N4 N 0.8788(5) 0.8698(2) 0.1639(2) 0.0418(10) Uani 1 1 d . . .
C8 C 0.8996(6) 0.7806(3) 0.1859(3) 0.0402(11) Uani 1 1 d . . .
C9 C 0.0963(7) 0.8441(3) 0.7960(3) 0.0457(13) Uani 1 1 d . . .
H9 H 0.1145 0.8281 0.8537 0.055 Uiso 1 1 calc R . .
C10 C 0.5237(7) 1.0578(4) 0.8029(3) 0.0484(13) Uani 1 1 d . . .
C11 C 0.6177(6) 0.8493(3) 0.0382(3) 0.0393(11) Uani 1 1 d . . .
C12 C 0.7004(7) 0.0881(4) 0.4188(3) 0.0546(14) Uani 1 1 d . . .
N7 N 0.1672(5) 0.7086(3) -0.0153(3) 0.0556(12) Uani 1 1 d . . .
H7A H 0.1626 0.6611 -0.0466 0.067 Uiso 1 1 calc R . .
H7B H 0.0793 0.7265 0.0056 0.067 Uiso 1 1 calc R . .
N10 N 0.6690(6) 0.1450(3) 0.4794(3) 0.0633(13) Uani 1 1 d . . .
H10A H 0.6576 0.1255 0.5299 0.076 Uiso 1 1 calc R . .
H10B H 0.6600 0.2013 0.4683 0.076 Uiso 1 1 calc R . .
C13 C 0.2304(6) 0.8493(3) 0.7506(3) 0.0440(12) Uani 1 1 d . . .
H13 H 0.3386 0.8375 0.7775 0.053 Uiso 1 1 calc R . .
C14 C 0.4571(7) 0.7273(3) -0.0323(3) 0.0474(13) Uani 1 1 d . . .
H14 H 0.4512 0.6774 -0.0681 0.057 Uiso 1 1 calc R . .
C15 C 0.3248(7) 0.8336(4) 0.0502(3) 0.0508(13) Uani 1 1 d . . .
H15 H 0.2285 0.8556 0.0700 0.061 Uiso 1 1 calc R . .
C16 C 0.5582(8) 1.1464(4) 0.7868(3) 0.0588(16) Uani 1 1 d . . .
H16 H 0.5804 1.1871 0.8317 0.071 Uiso 1 1 calc R . .
C17 C 0.5590(7) 1.1729(3) 0.7036(3) 0.0547(14) Uani 1 1 d . . .
C18 C 0.9210(7) 0.6819(4) 0.2979(4) 0.0584(15) Uani 1 1 d . . .
C19 C 0.9223(7) 0.6323(3) 0.1548(4) 0.0549(14) Uani 1 1 d . . .
N11 N 0.7687(6) -0.0268(4) 0.2913(3) 0.0677(14) Uani 1 1 d . . .
H11 H 0.7893 -0.0629 0.2513 0.081 Uiso 1 1 calc R . .
C20 C 0.6078(6) 0.7727(3) -0.0128(3) 0.0433(12) Uani 1 1 d . . .
H20 H 0.7035 0.7518 -0.0340 0.052 Uiso 1 1 calc R . .
C21 C 0.7160(7) -0.0034(4) 0.4333(4) 0.0611(15) Uani 1 1 d . . .
H21 H 0.7025 -0.0272 0.4867 0.073 Uiso 1 1 calc R . .
C22 C 0.7541(10) 0.0595(5) 0.2762(4) 0.081(2) Uani 1 1 d . . .
H22 H 0.7663 0.0806 0.2216 0.097 Uiso 1 1 calc R . .
C23 C 0.5258(9) 1.0214(4) 0.8916(3) 0.0697(18) Uani 1 1 d . . .
H23A H 0.4477 0.9726 0.8905 0.105 Uiso 1 1 calc R . .
H23B H 0.4943 1.0678 0.9287 0.105 Uiso 1 1 calc R . .
H23C H 0.6369 1.0005 0.9126 0.105 Uiso 1 1 calc R . .
C24 C 0.6082(9) 1.2657(4) 0.6826(4) 0.078(2) Uani 1 1 d . . .
H24A H 0.7257 1.2671 0.6767 0.118 Uiso 1 1 calc R . .
H24B H 0.5868 1.3056 0.7279 0.118 Uiso 1 1 calc R . .
H24C H 0.5436 1.2844 0.6297 0.118 Uiso 1 1 calc R . .
C25 C 0.9348(10) 0.5610(4) 0.0896(5) 0.089(2) Uani 1 1 d . . .
H25A H 0.8773 0.5801 0.0350 0.134 Uiso 1 1 calc R . .
H25B H 0.8841 0.5070 0.1071 0.134 Uiso 1 1 calc R . .
H25C H 1.0510 0.5501 0.0846 0.134 Uiso 1 1 calc R . .
C26 C 0.7515(7) -0.0579(4) 0.3686(4) 0.0718(17) Uani 1 1 d . . .
H26 H 0.7640 -0.1191 0.3790 0.086 Uiso 1 1 calc R . .
C27 C 0.9256(10) 0.6667(5) 0.3929(4) 0.088(2) Uani 1 1 d . . .
H27A H 1.0171 0.7000 0.4234 0.133 Uiso 1 1 calc R . .
H27B H 0.9410 0.6040 0.4053 0.133 Uiso 1 1 calc R . .
H27C H 0.8216 0.6865 0.4105 0.133 Uiso 1 1 calc R . .
C28 C 0.9276(8) 0.6128(4) 0.2414(4) 0.0680(17) Uani 1 1 d . . .
H28 H 0.9355 0.5538 0.2607 0.082 Uiso 1 1 calc R . .
C29 C 0.7225(9) 0.1179(4) 0.3361(4) 0.0749(19) Uani 1 1 d . . .
H29 H 0.7150 0.1788 0.3232 0.090 Uiso 1 1 calc R . .
N12 N 0.2833(6) 0.0397(4) 0.4243(3) 0.0662(14) Uani 1 1 d . . .
H12 H 0.3176 0.0234 0.4762 0.079 Uiso 1 1 calc R . .
C30 C 0.1736(9) 0.0012(4) 0.2844(4) 0.0747(19) Uani 1 1 d . . .
H30 H 0.1341 -0.0428 0.2449 0.090 Uiso 1 1 calc R . .
C31 C 0.2871(8) 0.1242(5) 0.4020(5) 0.0757(18) Uani 1 1 d . . .
H31 H 0.3244 0.1659 0.4443 0.091 Uiso 1 1 calc R . .
C32 C 0.2254(8) -0.0207(4) 0.3652(4) 0.0705(17) Uani 1 1 d . . .
H32 H 0.2212 -0.0805 0.3814 0.085 Uiso 1 1 calc R . .
C33 C 0.1783(9) 0.0905(5) 0.2587(4) 0.0762(19) Uani 1 1 d . . .
C34 C 0.2414(9) 0.1534(4) 0.3237(5) 0.0774(19) Uani 1 1 d . . .
H34 H 0.2498 0.2139 0.3106 0.093 Uiso 1 1 calc R . .
N9 N 0.1214(10) 0.1159(5) 0.1800(4) 0.129(3) Uani 1 1 d . . .
H9A H 0.0797 0.0770 0.1427 0.154 Uiso 1 1 calc R . .
H9B H 0.1258 0.1714 0.1659 0.154 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.440(3) . ?
S1 O1 1.441(4) . ?
S1 N1 1.584(4) . ?
S1 C3 1.766(5) . ?
S2 O4 1.435(3) . ?
S2 O3 1.448(3) . ?
S2 N4 1.584(4) . ?
S2 C11 1.766(5) . ?
C1 C11 1.379(6) . ?
C1 C15 1.380(7) . ?
C1 H1 0.9300 . ?
N3 C4 1.330(6) . ?
N3 C10 1.344(6) . ?
C2 C5 1.374(6) . ?
C2 C6 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C5 1.374(6) . ?
C3 C13 1.400(6) . ?
C4 N2 1.340(6) . ?
C4 N1 1.383(6) . ?
C5 H5 0.9300 . ?
C6 C9 1.380(7) . ?
C6 N8 1.386(6) . ?
N5 C19 1.337(6) . ?
N5 C8 1.338(6) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N2 C17 1.342(6) . ?
C7 N7 1.374(6) . ?
C7 C14 1.385(7) . ?
C7 C15 1.390(7) . ?
N6 C18 1.337(7) . ?
N6 C8 1.338(6) . ?
N4 C8 1.380(6) . ?
C9 C13 1.370(7) . ?
C9 H9 0.9300 . ?
C10 C16 1.381(7) . ?
C10 C23 1.492(7) . ?
C11 C20 1.392(6) . ?
C12 N10 1.324(6) . ?
C12 C21 1.387(7) . ?
C12 C29 1.406(7) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
C13 H13 0.9300 . ?
C14 C20 1.384(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.367(7) . ?
C16 H16 0.9300 . ?
C17 C24 1.489(7) . ?
C18 C28 1.366(8) . ?
C18 C27 1.504(8) . ?
C19 C28 1.385(8) . ?
C19 C25 1.489(8) . ?
N11 C22 1.312(8) . ?
N11 C26 1.324(7) . ?
N11 H11 0.8600 . ?
C20 H20 0.9300 . ?
C21 C26 1.362(8) . ?
C21 H21 0.9300 . ?
C22 C29 1.332(8) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
N12 C31 1.311(8) . ?
N12 C32 1.331(7) . ?
N12 H12 0.8600 . ?
C30 C32 1.322(8) . ?
C30 C33 1.395(9) . ?
C30 H30 0.9300 . ?
C31 C34 1.310(9) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 N9 1.314(7) . ?
C33 C34 1.428(9) . ?
C34 H34 0.9300 . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 114.9(2) . . ?
O2 S1 N1 104.4(2) . . ?
O1 S1 N1 114.5(2) . . ?
O2 S1 C3 105.7(2) . . ?
O1 S1 C3 107.0(2) . . ?
N1 S1 C3 110.0(2) . . ?
O4 S2 O3 115.1(2) . . ?
O4 S2 N4 115.3(2) . . ?
O3 S2 N4 104.2(2) . . ?
O4 S2 C11 106.8(2) . . ?
O3 S2 C11 107.9(2) . . ?
N4 S2 C11 107.1(2) . . ?
C11 C1 C15 120.4(5) . . ?
C11 C1 H1 119.8 . . ?
C15 C1 H1 119.8 . . ?
C4 N3 C10 116.5(4) . . ?
C5 C2 C6 120.8(4) . . ?
C5 C2 H2 119.6 . . ?
C6 C2 H2 119.6 . . ?
C5 C3 C13 119.1(4) . . ?
C5 C3 S1 120.3(3) . . ?
C13 C3 S1 120.6(4) . . ?
N3 C4 N2 125.9(4) . . ?
N3 C4 N1 120.3(4) . . ?
N2 C4 N1 113.8(4) . . ?
C4 N1 S1 119.7(3) . . ?
C3 C5 C2 120.6(4) . . ?
C3 C5 H5 119.7 . . ?
C2 C5 H5 119.7 . . ?
C2 C6 C9 118.6(4) . . ?
C2 C6 N8 121.5(5) . . ?
C9 C6 N8 119.8(4) . . ?
C19 N5 C8 116.9(4) . . ?
C6 N8 H8A 120.0 . . ?
C6 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C4 N2 C17 116.8(4) . . ?
N7 C7 C14 120.3(5) . . ?
N7 C7 C15 121.0(5) . . ?
C14 C7 C15 118.7(5) . . ?
C18 N6 C8 117.2(5) . . ?
C8 N4 S2 122.2(3) . . ?
N6 C8 N5 125.4(4) . . ?
N6 C8 N4 112.7(4) . . ?
N5 C8 N4 121.9(4) . . ?
C13 C9 C6 121.3(4) . . ?
C13 C9 H9 119.4 . . ?
C6 C9 H9 119.4 . . ?
N3 C10 C16 121.0(5) . . ?
N3 C10 C23 116.2(4) . . ?
C16 C10 C23 122.8(5) . . ?
C1 C11 C20 118.9(5) . . ?
C1 C11 S2 121.2(4) . . ?
C20 C11 S2 119.7(4) . . ?
N10 C12 C21 122.3(5) . . ?
N10 C12 C29 121.4(5) . . ?
C21 C12 C29 116.3(5) . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C12 N10 H10A 120.0 . . ?
C12 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C9 C13 C3 119.6(5) . . ?
C9 C13 H13 120.2 . . ?
C3 C13 H13 120.2 . . ?
C7 C14 C20 120.3(5) . . ?
C7 C14 H14 119.9 . . ?
C20 C14 H14 119.9 . . ?
C1 C15 C7 120.9(5) . . ?
C1 C15 H15 119.5 . . ?
C7 C15 H15 119.5 . . ?
C17 C16 C10 118.6(5) . . ?
C17 C16 H16 120.7 . . ?
C10 C16 H16 120.7 . . ?
N2 C17 C16 120.9(5) . . ?
N2 C17 C24 118.0(5) . . ?
C16 C17 C24 121.1(5) . . ?
N6 C18 C28 121.0(5) . . ?
N6 C18 C27 116.8(5) . . ?
C28 C18 C27 122.2(6) . . ?
N5 C19 C28 120.7(5) . . ?
N5 C19 C25 117.3(5) . . ?
C28 C19 C25 122.0(5) . . ?
C22 N11 C26 119.5(5) . . ?
C22 N11 H11 120.2 . . ?
C26 N11 H11 120.2 . . ?
C14 C20 C11 120.7(5) . . ?
C14 C20 H20 119.7 . . ?
C11 C20 H20 119.7 . . ?
C26 C21 C12 119.3(5) . . ?
C26 C21 H21 120.3 . . ?
C12 C21 H21 120.3 . . ?
N11 C22 C29 122.4(6) . . ?
N11 C22 H22 118.8 . . ?
C29 C22 H22 118.8 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C25 H25A 109.5 . . ?
C19 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C19 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N11 C26 C21 122.1(6) . . ?
N11 C26 H26 118.9 . . ?
C21 C26 H26 118.9 . . ?
C18 C27 H27A 109.5 . . ?
C18 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C18 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C18 C28 C19 118.7(5) . . ?
C18 C28 H28 120.6 . . ?
C19 C28 H28 120.6 . . ?
C22 C29 C12 120.3(6) . . ?
C22 C29 H29 119.8 . . ?
C12 C29 H29 119.8 . . ?
C31 N12 C32 118.9(5) . . ?
C31 N12 H12 120.5 . . ?
C32 N12 H12 120.5 . . ?
C32 C30 C33 119.7(6) . . ?
C32 C30 H30 120.1 . . ?
C33 C30 H30 120.1 . . ?
C34 C31 N12 123.8(6) . . ?
C34 C31 H31 118.1 . . ?
N12 C31 H31 118.1 . . ?
C30 C32 N12 122.5(6) . . ?
C30 C32 H32 118.7 . . ?
N12 C32 H32 118.7 . . ?
N9 C33 C30 121.9(7) . . ?
N9 C33 C34 121.8(7) . . ?
C30 C33 C34 116.2(6) . . ?
C31 C34 C33 118.7(6) . . ?
C31 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C33 N9 H9A 120.0 . . ?
C33 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C3 C5 -34.0(5) . . . . ?
O1 S1 C3 C5 -156.9(4) . . . . ?
N1 S1 C3 C5 78.1(4) . . . . ?
O2 S1 C3 C13 144.3(4) . . . . ?
O1 S1 C3 C13 21.4(4) . . . . ?
N1 S1 C3 C13 -103.5(4) . . . . ?
C10 N3 C4 N2 5.5(8) . . . . ?
C10 N3 C4 N1 -173.2(4) . . . . ?
N3 C4 N1 S1 -2.1(6) . . . . ?
N2 C4 N1 S1 179.0(4) . . . . ?
O2 S1 N1 C4 174.7(4) . . . . ?
O1 S1 N1 C4 -58.8(4) . . . . ?
C3 S1 N1 C4 61.7(4) . . . . ?
C13 C3 C5 C2 0.9(7) . . . . ?
S1 C3 C5 C2 179.2(4) . . . . ?
C6 C2 C5 C3 -0.6(8) . . . . ?
C5 C2 C6 C9 -0.3(7) . . . . ?
C5 C2 C6 N8 -177.2(5) . . . . ?
N3 C4 N2 C17 -4.7(8) . . . . ?
N1 C4 N2 C17 174.0(4) . . . . ?
O4 S2 N4 C8 -61.4(4) . . . . ?
O3 S2 N4 C8 171.5(4) . . . . ?
C11 S2 N4 C8 57.3(4) . . . . ?
C18 N6 C8 N5 -2.6(8) . . . . ?
C18 N6 C8 N4 177.7(4) . . . . ?
C19 N5 C8 N6 3.7(7) . . . . ?
C19 N5 C8 N4 -176.5(5) . . . . ?
S2 N4 C8 N6 -161.9(3) . . . . ?
S2 N4 C8 N5 18.3(7) . . . . ?
C2 C6 C9 C13 0.9(7) . . . . ?
N8 C6 C9 C13 177.9(4) . . . . ?
C4 N3 C10 C16 -1.6(8) . . . . ?
C4 N3 C10 C23 178.2(5) . . . . ?
C15 C1 C11 C20 -0.9(7) . . . . ?
C15 C1 C11 S2 -175.4(4) . . . . ?
O4 S2 C11 C1 -161.4(4) . . . . ?
O3 S2 C11 C1 -37.1(4) . . . . ?
N4 S2 C11 C1 74.6(4) . . . . ?
O4 S2 C11 C20 24.2(4) . . . . ?
O3 S2 C11 C20 148.5(4) . . . . ?
N4 S2 C11 C20 -99.8(4) . . . . ?
C6 C9 C13 C3 -0.6(7) . . . . ?
C5 C3 C13 C9 -0.3(7) . . . . ?
S1 C3 C13 C9 -178.7(4) . . . . ?
N7 C7 C14 C20 -177.4(4) . . . . ?
C15 C7 C14 C20 3.9(7) . . . . ?
C11 C1 C15 C7 2.6(7) . . . . ?
N7 C7 C15 C1 177.2(4) . . . . ?
C14 C7 C15 C1 -4.1(7) . . . . ?
N3 C10 C16 C17 -2.5(9) . . . . ?
C23 C10 C16 C17 177.7(6) . . . . ?
C4 N2 C17 C16 0.1(8) . . . . ?
C4 N2 C17 C24 178.7(5) . . . . ?
C10 C16 C17 N2 3.3(9) . . . . ?
C10 C16 C17 C24 -175.3(6) . . . . ?
C8 N6 C18 C28 0.0(8) . . . . ?
C8 N6 C18 C27 -178.8(5) . . . . ?
C8 N5 C19 C28 -2.4(8) . . . . ?
C8 N5 C19 C25 179.8(5) . . . . ?
C7 C14 C20 C11 -2.3(7) . . . . ?
C1 C11 C20 C14 0.8(7) . . . . ?
S2 C11 C20 C14 175.3(4) . . . . ?
N10 C12 C21 C26 -178.8(6) . . . . ?
C29 C12 C21 C26 0.2(9) . . . . ?
C26 N11 C22 C29 0.1(11) . . . . ?
C22 N11 C26 C21 1.1(10) . . . . ?
C12 C21 C26 N11 -1.2(9) . . . . ?
N6 C18 C28 C19 1.1(9) . . . . ?
C27 C18 C28 C19 179.8(6) . . . . ?
N5 C19 C28 C18 0.1(9) . . . . ?
C25 C19 C28 C18 177.8(6) . . . . ?
N11 C22 C29 C12 -1.1(12) . . . . ?
N10 C12 C29 C22 179.9(7) . . . . ?
C21 C12 C29 C22 1.0(10) . . . . ?
C32 N12 C31 C34 -2.0(11) . . . . ?
C33 C30 C32 N12 -0.2(10) . . . . ?
C31 N12 C32 C30 1.0(10) . . . . ?
C32 C30 C33 N9 -177.0(7) . . . . ?
C32 C30 C33 C34 0.3(10) . . . . ?
N12 C31 C34 C33 2.2(11) . . . . ?
N9 C33 C34 C31 176.1(8) . . . . ?
C30 C33 C34 C31 -1.2(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_snddm
_database_code_depnum_ccdc_archive 'CCDC 1500510'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
;  
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F3 N2 O2, C12 H14 N4 O2 S'
_chemical_formula_sum            'C25 H23 F3 N6 O4 S'
_chemical_formula_weight         560.55

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'
F F 0.0171 0.0103 '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           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_hall  -P2ac2ab

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

_cell_length_a                   15.840(2)
_cell_length_b                   14.613(2)
_cell_length_c                   21.829(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5052.8(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1165
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      20.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .52
_exptl_crystal_size_mid          .32
_exptl_crystal_size_min          .15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2320.0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .877
_exptl_absorpt_correction_T_max  .979
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            25363
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4448
_reflns_number_gt                3550
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0577P)²+3.4553P] 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         4448
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.74900(16) 0.72119(17) 0.16177(11) 0.0277(6) Uani 1 1 d . . .
H1 H 0.7790 0.6929 0.1931 0.033 Uiso 1 1 calc R . .
C2 C 0.66213(16) 0.72245(17) 0.16593(11) 0.0294(6) Uani 1 1 d . . .
H2 H 0.6345 0.6967 0.1993 0.035 Uiso 1 1 calc R . .
C3 C 0.61757(16) 0.76313(17) 0.11900(11) 0.0265(6) Uani 1 1 d . . .
H3 H 0.5589 0.7651 0.1205 0.032 Uiso 1 1 calc R . .
C4 C 0.66015(15) 0.80120(16) 0.06939(10) 0.0221(5) Uani 1 1 d . . .
C5 C 0.75001(15) 0.79665(16) 0.06985(10) 0.0234(5) Uani 1 1 d . . .
C6 C 0.88130(15) 0.84911(16) 0.01560(11) 0.0233(5) Uani 1 1 d . . .
C7 C 0.90833(16) 0.87688(18) -0.04259(11) 0.0279(6) Uani 1 1 d . . .
H7 H 0.8692 0.8822 -0.0742 0.033 Uiso 1 1 calc R . .
C8 C 0.99209(16) 0.89640(18) -0.05379(11) 0.0302(6) Uani 1 1 d . . .
H8 H 1.0090 0.9149 -0.0927 0.036 Uiso 1 1 calc R . .
C9 C 1.05097(16) 0.88851(18) -0.00749(11) 0.0290(6) Uani 1 1 d . . .
H9 H 1.1075 0.9018 -0.0148 0.035 Uiso 1 1 calc R . .
C10 C 1.02473(15) 0.86055(17) 0.04997(11) 0.0267(6) Uani 1 1 d . . .
C11 C 0.94080(16) 0.84090(17) 0.06228(11) 0.0271(6) Uani 1 1 d . . .
H11 H 0.9244 0.8224 0.1013 0.032 Uiso 1 1 calc R . .
C12 C 1.08693(17) 0.8529(2) 0.10111(12) 0.0338(6) Uani 1 1 d . . .
C13 C 0.80656(15) 0.52792(17) 0.09015(11) 0.0269(6) Uani 1 1 d . . .
H13 H 0.7498 0.5198 0.0807 0.032 Uiso 1 1 calc R . .
C14 C 0.83758(15) 0.50224(16) 0.14695(11) 0.0236(5) Uani 1 1 d . . .
C15 C 0.86065(15) 0.56543(16) 0.04800(11) 0.0239(5) Uani 1 1 d . . .
C16 C 0.96738(14) 0.54996(15) 0.11785(10) 0.0196(5) Uani 1 1 d . . .
C18 C 1.10794(14) 0.41767(16) 0.19820(10) 0.0203(5) Uani 1 1 d . . .
C19 C 1.04595(14) 0.36864(17) 0.22953(10) 0.0233(5) Uani 1 1 d . . .
H19 H 1.0011 0.3993 0.2479 0.028 Uiso 1 1 calc R . .
C20 C 1.05125(15) 0.27500(17) 0.23323(11) 0.0248(6) Uani 1 1 d . . .
H20 H 1.0100 0.2426 0.2544 0.030 Uiso 1 1 calc R . .
C21 C 1.11791(15) 0.22753(16) 0.20557(10) 0.0217(5) Uani 1 1 d . . .
C22 C 1.18060(15) 0.27803(17) 0.17519(10) 0.0250(6) Uani 1 1 d . . .
H22 H 1.2261 0.2478 0.1574 0.030 Uiso 1 1 calc R . .
C23 C 1.17547(15) 0.37151(17) 0.17150(10) 0.0235(5) Uani 1 1 d . . .
H23 H 1.2172 0.4042 0.1511 0.028 Uiso 1 1 calc R . .
C24 C 0.83299(16) 0.5954(2) -0.01415(11) 0.0334(6) Uani 1 1 d . . .
H24A H 0.8275 0.6608 -0.0148 0.050 Uiso 1 1 calc R . .
H24B H 0.7795 0.5679 -0.0237 0.050 Uiso 1 1 calc R . .
H24C H 0.8741 0.5768 -0.0439 0.050 Uiso 1 1 calc R . .
C25 C 0.78227(16) 0.46233(19) 0.19526(11) 0.0313(6) Uani 1 1 d . . .
H25A H 0.8144 0.4204 0.2198 0.047 Uiso 1 1 calc R . .
H25B H 0.7362 0.4304 0.1764 0.047 Uiso 1 1 calc R . .
H25C H 0.7606 0.5105 0.2207 0.047 Uiso 1 1 calc R . .
C26 C 0.61229(15) 0.84316(16) 0.01879(11) 0.0237(5) Uani 1 1 d . . .
F1 F 1.07149(11) 0.78336(14) 0.13897(8) 0.0563(5) Uani 1 1 d . . .
F2 F 1.16499(10) 0.83836(18) 0.08166(8) 0.0731(7) Uani 1 1 d . . .
F3 F 1.08802(16) 0.92556(14) 0.13710(10) 0.0812(8) Uani 1 1 d . . .
N1 N 0.79486(12) 0.83398(15) 0.02240(9) 0.0274(5) Uani 1 1 d . . .
H1A H 0.7647 0.8509 -0.0083 0.033 Uiso 1 1 calc R . .
N2 N 1.05239(12) 0.56245(14) 0.12985(9) 0.0235(5) Uani 1 1 d . . .
H200 H 1.0819 0.5863 0.1009 0.028 Uiso 1 1 calc R . .
N3 N 0.94318(12) 0.57695(13) 0.06166(8) 0.0212(4) Uani 1 1 d . . .
N4 N 0.91939(12) 0.51352(13) 0.16116(9) 0.0221(4) Uani 1 1 d . . .
N5 N 1.12269(13) 0.13449(14) 0.20852(9) 0.0295(5) Uani 1 1 d . . .
H5A H 1.0844 0.1040 0.2276 0.035 Uiso 1 1 calc R . .
H5B H 1.1640 0.1063 0.1913 0.035 Uiso 1 1 calc R . .
N6 N 0.79281(13) 0.75786(14) 0.11571(9) 0.0255(5) Uani 1 1 d . . .
O1 O 1.05655(11) 0.57110(12) 0.24416(7) 0.0282(4) Uani 1 1 d . . .
O2 O 1.18615(10) 0.57153(12) 0.18110(8) 0.0295(4) Uani 1 1 d . . .
O3 O 0.64540(11) 0.86916(12) -0.02923(7) 0.0300(4) Uani 1 1 d . . .
O4 O 0.53131(10) 0.85068(13) 0.02908(8) 0.0304(4) Uani 1 1 d . . .
H4 H 0.5083 0.8737 -0.0009 0.046 Uiso 1 1 calc R . .
S1 S 1.10309(4) 0.53672(4) 0.19312(3) 0.02167(17) Uani 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
C1 N6 1.334(3) . ?
C1 C2 1.379(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.425(3) . ?
C4 C26 1.473(3) . ?
C5 N6 1.335(3) . ?
C5 N1 1.369(3) . ?
C6 C11 1.393(3) . ?
C6 N1 1.395(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.379(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 C12 1.493(4) . ?
C11 H11 0.9300 . ?
C12 F3 1.321(3) . ?
C12 F2 1.324(3) . ?
C12 F1 1.332(3) . ?
C13 C15 1.372(3) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9300 . ?
C14 N4 1.343(3) . ?
C14 C25 1.490(3) . ?
C15 N3 1.351(3) . ?
C15 C24 1.491(3) . ?
C16 N4 1.325(3) . ?
C16 N3 1.344(3) . ?
C16 N2 1.384(3) . ?
C18 C23 1.392(3) . ?
C18 C19 1.395(3) . ?
C18 S1 1.745(2) . ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.400(3) . ?
C20 H20 0.9300 . ?
C21 N5 1.363(3) . ?
C21 C22 1.404(3) . ?
C22 C23 1.371(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 O3 1.232(3) . ?
C26 O4 1.307(3) . ?
N1 H1A 0.8600 . ?
N2 S1 1.6414(19) . ?
N2 H200 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
O1 S1 1.4273(17) . ?
O2 S1 1.4347(17) . ?
O4 H4 0.8200 . ?

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
N6 C1 C2 124.3(2) . . ?
N6 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 117.4(2) . . ?
C3 C4 C26 120.0(2) . . ?
C5 C4 C26 122.6(2) . . ?
N6 C5 N1 118.2(2) . . ?
N6 C5 C4 122.2(2) . . ?
N1 C5 C4 119.6(2) . . ?
C11 C6 N1 124.9(2) . . ?
C11 C6 C7 118.8(2) . . ?
N1 C6 C7 116.3(2) . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C10 C11 121.7(2) . . ?
C9 C10 C12 120.1(2) . . ?
C11 C10 C12 118.2(2) . . ?
C10 C11 C6 119.3(2) . . ?
C10 C11 H11 120.4 . . ?
C6 C11 H11 120.4 . . ?
F3 C12 F2 107.9(2) . . ?
F3 C12 F1 104.3(2) . . ?
F2 C12 F1 104.4(2) . . ?
F3 C12 C10 113.1(2) . . ?
F2 C12 C10 112.9(2) . . ?
F1 C12 C10 113.6(2) . . ?
C15 C13 C14 119.1(2) . . ?
C15 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N4 C14 C13 121.1(2) . . ?
N4 C14 C25 116.9(2) . . ?
C13 C14 C25 122.1(2) . . ?
N3 C15 C13 120.4(2) . . ?
N3 C15 C24 116.6(2) . . ?
C13 C15 C24 123.0(2) . . ?
N4 C16 N3 127.3(2) . . ?
N4 C16 N2 118.4(2) . . ?
N3 C16 N2 114.3(2) . . ?
C23 C18 C19 119.8(2) . . ?
C23 C18 S1 119.35(18) . . ?
C19 C18 S1 120.82(18) . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 121.0(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
N5 C21 C20 121.0(2) . . ?
N5 C21 C22 120.5(2) . . ?
C20 C21 C22 118.5(2) . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C18 120.2(2) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C14 C25 H25A 109.5 . . ?
C14 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C14 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 O4 122.6(2) . . ?
O3 C26 C4 123.2(2) . . ?
O4 C26 C4 114.3(2) . . ?
C5 N1 C6 130.8(2) . . ?
C5 N1 H1A 114.6 . . ?
C6 N1 H1A 114.6 . . ?
C16 N2 S1 127.24(16) . . ?
C16 N2 H200 116.4 . . ?
S1 N2 H200 116.4 . . ?
C16 N3 C15 116.1(2) . . ?
C16 N4 C14 116.0(2) . . ?
C21 N5 H5A 120.0 . . ?
C21 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C1 N6 C5 118.1(2) . . ?
C26 O4 H4 109.5 . . ?
O1 S1 O2 119.44(11) . . ?
O1 S1 N2 108.87(10) . . ?
O2 S1 N2 102.33(10) . . ?
O1 S1 C18 108.92(11) . . ?
O2 S1 C18 108.95(11) . . ?
N2 S1 C18 107.66(10) . . ?

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
N6 C1 C2 C3 1.0(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C26 178.9(2) . . . . ?
C3 C4 C5 N6 -0.2(3) . . . . ?
C26 C4 C5 N6 -179.5(2) . . . . ?
C3 C4 C5 N1 -179.3(2) . . . . ?
C26 C4 C5 N1 1.4(3) . . . . ?
C11 C6 C7 C8 -0.4(4) . . . . ?
N1 C6 C7 C8 178.0(2) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C8 C9 C10 C12 -179.0(2) . . . . ?
C9 C10 C11 C6 0.3(4) . . . . ?
C12 C10 C11 C6 178.9(2) . . . . ?
N1 C6 C11 C10 -178.1(2) . . . . ?
C7 C6 C11 C10 0.1(4) . . . . ?
C9 C10 C12 F3 97.3(3) . . . . ?
C11 C10 C12 F3 -81.4(3) . . . . ?
C9 C10 C12 F2 -25.6(4) . . . . ?
C11 C10 C12 F2 155.8(2) . . . . ?
C9 C10 C12 F1 -144.1(3) . . . . ?
C11 C10 C12 F1 37.2(3) . . . . ?
C15 C13 C14 N4 0.0(4) . . . . ?
C15 C13 C14 C25 179.1(2) . . . . ?
C14 C13 C15 N3 0.2(3) . . . . ?
C14 C13 C15 C24 -179.8(2) . . . . ?
C23 C18 C19 C20 -0.8(3) . . . . ?
S1 C18 C19 C20 -179.65(18) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 N5 -179.1(2) . . . . ?
C19 C20 C21 C22 1.6(3) . . . . ?
N5 C21 C22 C23 179.2(2) . . . . ?
C20 C21 C22 C23 -1.5(3) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?
C19 C18 C23 C22 0.9(3) . . . . ?
S1 C18 C23 C22 179.75(18) . . . . ?
C3 C4 C26 O3 -172.0(2) . . . . ?
C5 C4 C26 O3 7.3(4) . . . . ?
C3 C4 C26 O4 8.1(3) . . . . ?
C5 C4 C26 O4 -172.6(2) . . . . ?
N6 C5 N1 C6 -8.6(4) . . . . ?
C4 C5 N1 C6 170.6(2) . . . . ?
C11 C6 N1 C5 -10.6(4) . . . . ?
C7 C6 N1 C5 171.1(2) . . . . ?
N4 C16 N2 S1 0.1(3) . . . . ?
N3 C16 N2 S1 -179.59(16) . . . . ?
N4 C16 N3 C15 -0.1(3) . . . . ?
N2 C16 N3 C15 179.64(19) . . . . ?
C13 C15 N3 C16 -0.1(3) . . . . ?
C24 C15 N3 C16 179.8(2) . . . . ?
N3 C16 N4 C14 0.2(3) . . . . ?
N2 C16 N4 C14 -179.5(2) . . . . ?
C13 C14 N4 C16 -0.2(3) . . . . ?
C25 C14 N4 C16 -179.3(2) . . . . ?
C2 C1 N6 C5 -1.5(4) . . . . ?
N1 C5 N6 C1 -179.7(2) . . . . ?
C4 C5 N6 C1 1.1(3) . . . . ?
C16 N2 S1 O1 -48.0(2) . . . . ?
C16 N2 S1 O2 -175.3(2) . . . . ?
C16 N2 S1 C18 69.9(2) . . . . ?
C23 C18 S1 O1 -153.07(17) . . . . ?
C19 C18 S1 O1 25.8(2) . . . . ?
C23 C18 S1 O2 -21.2(2) . . . . ?
C19 C18 S1 O2 157.61(18) . . . . ?
C23 C18 S1 N2 89.02(19) . . . . ?
C19 C18 S1 N2 -92.13(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_j5am
_database_code_depnum_ccdc_archive 'CCDC 1500516'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
;  
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N3 O3 S, 0.5(C4 H12 N2)'
_chemical_formula_sum            'C12 H16 N4 O3 S'
_chemical_formula_weight         296.35

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           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                   8.0883(15)
_cell_length_b                   8.2003(16)
_cell_length_c                   11.818(2)
_cell_angle_alpha                108.255(3)
_cell_angle_beta                 94.274(5)
_cell_angle_gamma                104.221(3)
_cell_volume                     711.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1065
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      24.97

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          .42
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .740
_exptl_absorpt_correction_T_max  .937
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            2501
_diffrn_reflns_av_R_equivalents  0.0071
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2501
_reflns_number_gt                2501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1441P)²+0.4411P] 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         2501
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1972
_refine_ls_wR_factor_gt          0.1905
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 0.17224(11) 1.01148(10) 0.85018(8) 0.0363(5) Uani 1 1 d . . .
O2 O 0.2263(4) 1.0288(3) 0.9728(2) 0.0472(9) Uani 1 1 d . . .
O1 O 0.0801(3) 1.1353(3) 0.8324(2) 0.0408(8) Uani 1 1 d . . .
C1 C 0.3649(5) 1.1231(4) 0.6918(4) 0.0365(13) Uani 1 1 d . . .
H1 H 0.2705 1.1564 0.6665 0.044 Uiso 1 1 calc R . .
O3 O -0.1245(4) 0.7184(3) 0.4877(2) 0.0507(9) Uani 1 1 d . . .
C2 C -0.0297(5) 0.7446(4) 0.6705(3) 0.0346(10) Uani 1 1 d . . .
C3 C 0.3570(5) 1.0472(4) 0.7834(3) 0.0330(11) Uani 1 1 d . . .
N2 N 0.0588(4) 0.8078(3) 0.7872(3) 0.0386(10) Uani 1 1 d . . .
N1 N 0.8011(5) 1.1309(4) 0.6263(4) 0.0508(12) Uani 1 1 d . . .
H1A H 0.8901 1.1041 0.6512 0.061 Uiso 1 1 calc R . .
H1B H 0.8049 1.1786 0.5709 0.061 Uiso 1 1 calc R . .
C4 C 0.4987(5) 0.9957(4) 0.8186(3) 0.0352(13) Uani 1 1 d . . .
H4 H 0.4950 0.9442 0.8786 0.042 Uiso 1 1 calc R . .
C5 C -0.1522(5) 0.5744(4) 0.6156(4) 0.0457(12) Uani 1 1 d . . .
H5 H -0.1873 0.4866 0.6501 0.055 Uiso 1 1 calc R . .
N4 N 0.0148(5) 0.6473(4) 0.9571(3) 0.0522(11) Uani 1 1 d . . .
H4A H 0.0225 0.6915 0.8963 0.063 Uiso 1 1 calc R . .
H4B H 0.0171 0.7372 1.0251 0.063 Uiso 1 1 calc R . .
N3 N -0.0091(4) 0.8336(4) 0.5959(3) 0.0486(11) Uani 1 1 d . . .
C6 C 0.6532(5) 1.0979(4) 0.6750(4) 0.0376(13) Uani 1 1 d . . .
C7 C 0.5089(5) 1.1483(4) 0.6399(4) 0.0427(14) Uani 1 1 d . . .
H7 H 0.5122 1.1999 0.5800 0.051 Uiso 1 1 calc R . .
C8 C 0.6436(5) 1.0204(4) 0.7654(3) 0.0356(12) Uani 1 1 d . . .
H8 H 0.7370 0.9851 0.7898 0.043 Uiso 1 1 calc R . .
C9 C -0.2058(5) 0.5666(4) 0.5055(4) 0.0440(12) Uani 1 1 d . . .
C10 C 0.1635(6) 0.5783(5) 0.9720(4) 0.0550(14) Uani 1 1 d . . .
H10A H 0.2696 0.6756 0.9935 0.066 Uiso 1 1 calc R . .
H10B H 0.1678 0.4897 0.8962 0.066 Uiso 1 1 calc R . .
C11 C -0.1497(6) 0.5055(5) 0.9308(4) 0.0604(15) Uani 1 1 d . . .
H11A H -0.1571 0.4141 0.8535 0.072 Uiso 1 1 calc R . .
H11B H -0.2454 0.5559 0.9254 0.072 Uiso 1 1 calc R . .
C12 C -0.3326(6) 0.4291(5) 0.4007(4) 0.0603(14) Uani 1 1 d . . .
H12A H -0.3757 0.3222 0.4193 0.090 Uiso 1 1 calc R . .
H12B H -0.2768 0.4023 0.3310 0.090 Uiso 1 1 calc R . .
H12C H -0.4270 0.4744 0.3842 0.090 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.435(3) . ?
S1 O1 1.454(2) . ?
S1 N2 1.597(3) . ?
S1 C3 1.746(4) . ?
C1 C7 1.358(6) . ?
C1 C3 1.405(6) . ?
C1 H1 0.9300 . ?
O3 C9 1.345(5) . ?
O3 N3 1.425(4) . ?
C2 N3 1.304(5) . ?
C2 N2 1.381(4) . ?
C2 C5 1.417(4) . ?
C3 C4 1.394(5) . ?
N1 C6 1.370(6) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C4 C8 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C9 1.318(5) . ?
C5 H5 0.9300 . ?
N4 C10 1.470(6) . ?
N4 C11 1.474(5) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
C6 C8 1.402(6) . ?
C6 C7 1.407(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C12 1.492(5) . ?
C10 C11 1.510(6) 2_567 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C10 1.510(6) 2_567 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
O2 S1 O1 116.60(16) . . ?
O2 S1 N2 104.93(15) . . ?
O1 S1 N2 111.78(14) . . ?
O2 S1 C3 107.84(16) . . ?
O1 S1 C3 106.46(16) . . ?
N2 S1 C3 109.04(16) . . ?
C7 C1 C3 120.6(3) . . ?
C7 C1 H1 119.7 . . ?
C3 C1 H1 119.7 . . ?
C9 O3 N3 108.2(3) . . ?
N3 C2 N2 124.1(3) . . ?
N3 C2 C5 111.3(3) . . ?
N2 C2 C5 124.5(3) . . ?
C4 C3 C1 118.8(4) . . ?
C4 C3 S1 119.8(3) . . ?
C1 C3 S1 121.4(3) . . ?
C2 N2 S1 121.8(2) . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C8 C4 C3 120.4(3) . . ?
C8 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C9 C5 C2 105.5(3) . . ?
C9 C5 H5 127.3 . . ?
C2 C5 H5 127.3 . . ?
C10 N4 C11 111.2(3) . . ?
C10 N4 H4A 109.4 . . ?
C11 N4 H4A 109.4 . . ?
C10 N4 H4B 109.4 . . ?
C11 N4 H4B 109.4 . . ?
H4A N4 H4B 108.0 . . ?
C2 N3 O3 104.8(3) . . ?
N1 C6 C8 121.1(3) . . ?
N1 C6 C7 121.0(4) . . ?
C8 C6 C7 117.8(5) . . ?
C1 C7 C6 121.2(4) . . ?
C1 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C4 C8 C6 121.2(3) . . ?
C4 C8 H8 119.4 . . ?
C6 C8 H8 119.4 . . ?
C5 C9 O3 110.2(3) . . ?
C5 C9 C12 134.2(4) . . ?
O3 C9 C12 115.6(4) . . ?
N4 C10 C11 110.7(4) . 2_567 ?
N4 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 2_567 . ?
N4 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 2_567 . ?
H10A C10 H10B 108.1 . . ?
N4 C11 C10 111.0(3) . 2_567 ?
N4 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 2_567 . ?
N4 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 2_567 . ?
H11A C11 H11B 108.0 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C7 C1 C3 C4 -1.0(5) . . . . ?
C7 C1 C3 S1 -179.3(2) . . . . ?
O2 S1 C3 C4 32.6(3) . . . . ?
O1 S1 C3 C4 158.5(2) . . . . ?
N2 S1 C3 C4 -80.8(3) . . . . ?
O2 S1 C3 C1 -149.1(3) . . . . ?
O1 S1 C3 C1 -23.2(3) . . . . ?
N2 S1 C3 C1 97.5(3) . . . . ?
N3 C2 N2 S1 10.8(6) . . . . ?
C5 C2 N2 S1 -170.2(3) . . . . ?
O2 S1 N2 C2 173.8(3) . . . . ?
O1 S1 N2 C2 46.5(4) . . . . ?
C3 S1 N2 C2 -70.9(3) . . . . ?
C1 C3 C4 C8 0.6(5) . . . . ?
S1 C3 C4 C8 179.0(2) . . . . ?
N3 C2 C5 C9 -0.9(5) . . . . ?
N2 C2 C5 C9 180.0(4) . . . . ?
N2 C2 N3 O3 179.9(3) . . . . ?
C5 C2 N3 O3 0.8(4) . . . . ?
C9 O3 N3 C2 -0.4(4) . . . . ?
C3 C1 C7 C6 0.7(5) . . . . ?
N1 C6 C7 C1 -177.0(3) . . . . ?
C8 C6 C7 C1 0.1(5) . . . . ?
C3 C4 C8 C6 0.1(5) . . . . ?
N1 C6 C8 C4 176.6(3) . . . . ?
C7 C6 C8 C4 -0.5(5) . . . . ?
C2 C5 C9 O3 0.6(5) . . . . ?
C2 C5 C9 C12 -179.6(5) . . . . ?
N3 O3 C9 C5 -0.1(5) . . . . ?
N3 O3 C9 C12 -179.9(3) . . . . ?
C11 N4 C10 C11 -56.1(5) . . . 2_567 ?
C10 N4 C11 C10 56.3(6) . . . 2_567 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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_smx4pm
_database_code_depnum_ccdc_archive 'CCDC 1500515'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
;  
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N4 O2 S, 0.5(C4 H12 N2)'
_chemical_formula_sum            'C14 H19 N5 O2 S'
_chemical_formula_weight         321.40

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   P2(1)/c
_symmetry_space_group_name_hall  '-P 2ybc'

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

_cell_length_a                   6.2696(12)
_cell_length_b                   13.417(3)
_cell_length_c                   19.801(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.890(4)
_cell_angle_gamma                90.00
_cell_volume                     1659.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1949
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      23.60

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .43
_exptl_crystal_size_mid          .33
_exptl_crystal_size_min          .18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .889
_exptl_absorpt_correction_T_max  .998
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            6902
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2926
_reflns_number_gt                2328
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0521P)²+1.3829P] 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         2926
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.39140(11) 0.83249(5) 0.36675(3) 0.0355(2) Uani 1 1 d . . .
O4 O 0.6190(3) 0.84708(15) 0.36197(10) 0.0457(5) Uani 1 1 d . . .
N2 N 0.3204(4) 0.83597(17) 0.44107(11) 0.0381(6) Uani 1 1 d . . .
O3 O 0.2584(3) 0.90465(15) 0.32945(10) 0.0485(5) Uani 1 1 d . . .
C1 C 0.3286(4) 0.7143(2) 0.33288(13) 0.0373(6) Uani 1 1 d . . .
N1 N 0.1671(4) 0.4377(2) 0.25025(13) 0.0546(7) Uani 1 1 d . . .
H1A H 0.0400 0.4144 0.2522 0.066 Uiso 1 1 calc R . .
H1B H 0.2621 0.4029 0.2320 0.066 Uiso 1 1 calc R . .
N6 N 0.9301(4) 0.9170(2) 0.45958(14) 0.0539(7) Uani 1 1 d . . .
H6A H 1.0546 0.8849 0.4558 0.065 Uiso 1 1 calc R . .
H6B H 0.8252 0.8819 0.4366 0.065 Uiso 1 1 calc R . .
N3 N 0.2917(5) 0.7671(2) 0.54438(12) 0.0508(7) Uani 1 1 d . . .
C2 C 0.4785(5) 0.6571(2) 0.30406(16) 0.0468(8) Uani 1 1 d . . .
H2 H 0.6184 0.6801 0.3040 0.056 Uiso 1 1 calc R . .
C3 C 0.4241(5) 0.5670(2) 0.27554(16) 0.0494(8) Uani 1 1 d . . .
H3 H 0.5269 0.5299 0.2555 0.059 Uiso 1 1 calc R . .
C4 C 0.1230(5) 0.6788(2) 0.33311(16) 0.0502(8) Uani 1 1 d . . .
H4 H 0.0196 0.7170 0.3520 0.060 Uiso 1 1 calc R . .
C5 C 0.4001(5) 0.7680(2) 0.48921(13) 0.0388(7) Uani 1 1 d . . .
N4 N 0.5675(4) 0.7119(2) 0.47826(13) 0.0526(7) Uani 1 1 d . . .
C6 C 0.2183(5) 0.5300(2) 0.27612(14) 0.0403(7) Uani 1 1 d . . .
C7 C 0.0694(5) 0.5875(3) 0.30569(17) 0.0523(8) Uani 1 1 d . . .
H7 H -0.0697 0.5639 0.3070 0.063 Uiso 1 1 calc R . .
C8 C 0.3583(7) 0.7034(3) 0.59280(16) 0.0664(10) Uani 1 1 d . . .
C9 C 0.9414(6) 1.0169(3) 0.42975(18) 0.0604(10) Uani 1 1 d . . .
H9A H 0.8043 1.0500 0.4310 0.072 Uiso 1 1 calc R . .
H9B H 0.9726 1.0112 0.3828 0.072 Uiso 1 1 calc R . .
C10 C 0.8881(6) 0.9227(3) 0.53186(19) 0.0613(9) Uani 1 1 d . . .
H10A H 0.8857 0.8561 0.5508 0.074 Uiso 1 1 calc R . .
H10B H 0.7494 0.9531 0.5359 0.074 Uiso 1 1 calc R . .
C11 C 0.6297(6) 0.6470(3) 0.5271(2) 0.0685(11) Uani 1 1 d . . .
C14 C 0.2356(9) 0.7029(4) 0.6548(2) 0.1064(18) Uani 1 1 d . . .
H14A H 0.2276 0.7695 0.6721 0.160 Uiso 1 1 calc R . .
H14B H 0.3072 0.6608 0.6888 0.160 Uiso 1 1 calc R . .
H14C H 0.0936 0.6781 0.6431 0.160 Uiso 1 1 calc R . .
C13 C 0.8138(8) 0.5804(4) 0.5129(3) 0.1096(18) Uani 1 1 d . . .
H13A H 0.7843 0.5494 0.4694 0.164 Uiso 1 1 calc R . .
H13B H 0.8323 0.5301 0.5473 0.164 Uiso 1 1 calc R . .
H13C H 0.9422 0.6194 0.5129 0.164 Uiso 1 1 calc R . .
C12 C 0.5285(8) 0.6410(3) 0.5850(2) 0.0820(13) Uani 1 1 d . . .
H12 H 0.5734 0.5955 0.6187 0.098 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.440(2) . ?
S1 O4 1.452(2) . ?
S1 N2 1.574(2) . ?
S1 C1 1.754(3) . ?
N2 C5 1.381(4) . ?
C1 C2 1.374(4) . ?
C1 C4 1.375(4) . ?
N1 C6 1.368(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N6 C9 1.468(5) . ?
N6 C10 1.479(4) . ?
N6 H6A 0.9000 . ?
N6 H6B 0.9000 . ?
N3 C8 1.325(4) . ?
N3 C5 1.335(4) . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C6 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C7 1.370(4) . ?
C4 H4 0.9300 . ?
C5 N4 1.325(4) . ?
N4 C11 1.334(4) . ?
C6 C7 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C12 1.375(6) . ?
C8 C14 1.503(5) . ?
C9 C10 1.497(5) 3_776 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C9 1.497(5) 3_776 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.359(6) . ?
C11 C13 1.505(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 113.92(13) . . ?
O3 S1 N2 105.20(12) . . ?
O4 S1 N2 114.51(12) . . ?
O3 S1 C1 108.10(13) . . ?
O4 S1 C1 106.67(13) . . ?
N2 S1 C1 108.19(13) . . ?
C5 N2 S1 120.75(19) . . ?
C2 C1 C4 118.9(3) . . ?
C2 C1 S1 121.6(2) . . ?
C4 C1 S1 119.5(2) . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C9 N6 C10 111.1(2) . . ?
C9 N6 H6A 109.4 . . ?
C10 N6 H6A 109.4 . . ?
C9 N6 H6B 109.4 . . ?
C10 N6 H6B 109.4 . . ?
H6A N6 H6B 108.0 . . ?
C8 N3 C5 116.6(3) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C6 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
C6 C3 H3 119.5 . . ?
C7 C4 C1 120.5(3) . . ?
C7 C4 H4 119.8 . . ?
C1 C4 H4 119.8 . . ?
N4 C5 N3 126.5(3) . . ?
N4 C5 N2 120.5(3) . . ?
N3 C5 N2 113.0(3) . . ?
C5 N4 C11 116.0(3) . . ?
N1 C6 C7 121.3(3) . . ?
N1 C6 C3 120.7(3) . . ?
C7 C6 C3 118.0(3) . . ?
C4 C7 C6 121.1(3) . . ?
C4 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
N3 C8 C12 120.8(3) . . ?
N3 C8 C14 116.3(4) . . ?
C12 C8 C14 123.0(4) . . ?
N6 C9 C10 110.3(3) . 3_776 ?
N6 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 3_776 . ?
N6 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 3_776 . ?
H9A C9 H9B 108.1 . . ?
N6 C10 C9 109.9(3) . 3_776 ?
N6 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 3_776 . ?
N6 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 3_776 . ?
H10A C10 H10B 108.2 . . ?
N4 C11 C12 121.4(4) . . ?
N4 C11 C13 115.6(4) . . ?
C12 C11 C13 122.9(4) . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 C8 118.7(3) . . ?
C11 C12 H12 120.6 . . ?
C8 C12 H12 120.6 . . ?

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
O3 S1 N2 C5 173.1(2) . . . . ?
O4 S1 N2 C5 -61.1(3) . . . . ?
C1 S1 N2 C5 57.7(3) . . . . ?
O3 S1 C1 C2 118.5(3) . . . . ?
O4 S1 C1 C2 -4.4(3) . . . . ?
N2 S1 C1 C2 -128.1(3) . . . . ?
O3 S1 C1 C4 -59.5(3) . . . . ?
O4 S1 C1 C4 177.6(2) . . . . ?
N2 S1 C1 C4 54.0(3) . . . . ?
C4 C1 C2 C3 0.6(5) . . . . ?
S1 C1 C2 C3 -177.4(2) . . . . ?
C1 C2 C3 C6 -1.3(5) . . . . ?
C2 C1 C4 C7 0.7(5) . . . . ?
S1 C1 C4 C7 178.7(3) . . . . ?
C8 N3 C5 N4 -0.2(5) . . . . ?
C8 N3 C5 N2 179.7(3) . . . . ?
S1 N2 C5 N4 13.4(4) . . . . ?
S1 N2 C5 N3 -166.5(2) . . . . ?
N3 C5 N4 C11 1.3(5) . . . . ?
N2 C5 N4 C11 -178.6(3) . . . . ?
C2 C3 C6 N1 -177.0(3) . . . . ?
C2 C3 C6 C7 0.7(5) . . . . ?
C1 C4 C7 C6 -1.3(5) . . . . ?
N1 C6 C7 C4 178.3(3) . . . . ?
C3 C6 C7 C4 0.6(5) . . . . ?
C5 N3 C8 C12 -1.1(5) . . . . ?
C5 N3 C8 C14 179.9(4) . . . . ?
C10 N6 C9 C10 57.8(4) . . . 3_776 ?
C9 N6 C10 C9 -57.6(4) . . . 3_776 ?
C5 N4 C11 C12 -1.2(6) . . . . ?
C5 N4 C11 C13 177.4(4) . . . . ?
N4 C11 C12 C8 0.0(7) . . . . ?
C13 C11 C12 C8 -178.4(4) . . . . ?
N3 C8 C12 C11 1.2(7) . . . . ?
C14 C8 C12 C11 -180.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.051
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sf4pacm
_database_code_depnum_ccdc_archive 'CCDC 1500512'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
;  
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 N4 O2 S, C5 H7 N2'
_chemical_formula_sum            'C16 H18 N6 O2 S'
_chemical_formula_weight         358.42

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                   7.871(2)
_cell_length_b                   9.438(3)
_cell_length_c                   12.417(4)
_cell_angle_alpha                101.990(6)
_cell_angle_beta                 103.624(7)
_cell_angle_gamma                103.701(6)
_cell_volume                     836.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1267
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      23.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .39
_exptl_crystal_size_mid          .23
_exptl_crystal_size_min          .14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .740
_exptl_absorpt_correction_T_max  .937
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            2952
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2952
_reflns_number_gt                1706
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1399P)²+0.3574P] 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         2952
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.2067
_refine_ls_wR_factor_gt          0.1668
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 1.02689(14) 0.16683(11) 0.71558(10) 0.0322(5) Uani 1 1 d . . .
O2 O 1.1292(4) 0.0845(3) 0.7774(3) 0.0432(10) Uani 1 1 d . . .
O1 O 1.0723(4) 0.1878(3) 0.6125(3) 0.0403(9) Uani 1 1 d . . .
N5 N 1.0736(5) 0.5702(4) 0.8632(3) 0.0338(10) Uani 1 1 d . . .
C1 C 0.7212(6) -0.0636(4) 0.5761(4) 0.0365(13) Uani 1 1 d . . .
H1 H 0.7943 -0.0869 0.5303 0.044 Uiso 1 1 calc R . .
N4 N 0.8799(6) 0.4174(4) 0.6750(4) 0.0344(11) Uani 1 1 d . . .
C2 C 0.7934(6) 0.0605(4) 0.6737(4) 0.0280(11) Uani 1 1 d . . .
C3 C 0.5413(6) -0.1526(5) 0.5470(4) 0.0351(13) Uani 1 1 d . . .
H3 H 0.4949 -0.2372 0.4829 0.042 Uiso 1 1 calc R . .
N2 N 0.7018(5) 0.6129(4) 0.9780(4) 0.0413(12) Uani 1 1 d . . .
H2 H 0.7832 0.6336 1.0435 0.050 Uiso 1 1 calc R . .
C4 C 0.9976(6) 0.4373(4) 0.7773(4) 0.0291(12) Uani 1 1 d . . .
N3 N 1.0575(5) 0.3216(4) 0.8085(3) 0.0351(11) Uani 1 1 d . . .
N6 N 0.2478(5) -0.2066(4) 0.5840(4) 0.0474(12) Uani 1 1 d . . .
H6A H 0.1801 -0.1848 0.6261 0.057 Uiso 1 1 calc R . .
H6B H 0.2037 -0.2839 0.5240 0.057 Uiso 1 1 calc R . .
C5 C 0.6829(6) 0.0948(5) 0.7408(4) 0.0361(13) Uani 1 1 d . . .
H5 H 0.7307 0.1762 0.8071 0.043 Uiso 1 1 calc R . .
C6 C 0.4436(6) 0.5461(5) 0.7668(4) 0.0311(13) Uani 1 1 d . . .
C7 C 0.5007(6) 0.0074(5) 0.7089(4) 0.0385(13) Uani 1 1 d . . .
H7 H 0.4259 0.0329 0.7528 0.046 Uiso 1 1 calc R . .
C8 C 0.4295(6) -0.1166(5) 0.6128(4) 0.0377(13) Uani 1 1 d . . .
C9 C 1.0265(7) 0.6906(5) 0.8407(5) 0.0428(15) Uani 1 1 d . . .
N1 N 0.3207(6) 0.5148(4) 0.6654(4) 0.0453(12) Uani 1 1 d . . .
H1A H 0.2795 0.4237 0.6204 0.054 Uiso 1 1 calc R . .
H1B H 0.2820 0.5856 0.6443 0.054 Uiso 1 1 calc R . .
C10 C 0.6416(8) 0.7221(6) 0.9459(5) 0.0434(15) Uani 1 1 d . . .
H10 H 0.6852 0.8197 0.9959 0.052 Uiso 1 1 calc R . .
C11 C 0.6368(7) 0.4706(5) 0.9089(5) 0.0381(13) Uani 1 1 d . . .
H11 H 0.6793 0.3951 0.9331 0.046 Uiso 1 1 calc R . .
C12 C 0.8360(7) 0.5402(5) 0.6574(5) 0.0428(14) Uani 1 1 d . . .
H12 H 0.7532 0.5303 0.5871 0.051 Uiso 1 1 calc R . .
C13 C 0.5118(8) 0.4346(5) 0.8057(5) 0.0439(16) Uani 1 1 d . . .
H13 H 0.4695 0.3349 0.7592 0.053 Uiso 1 1 calc R . .
C14 C 0.9054(8) 0.6805(5) 0.7365(5) 0.0441(15) Uani 1 1 d . . .
H14 H 0.8729 0.7643 0.7210 0.053 Uiso 1 1 calc R . .
C15 C 0.5216(8) 0.6952(5) 0.8449(5) 0.0472(16) Uani 1 1 d . . .
H15 H 0.4865 0.7753 0.8236 0.057 Uiso 1 1 calc R . .
C16 C 1.1098(8) 0.8370(5) 0.9342(5) 0.0619(17) Uani 1 1 d . . .
H16A H 1.0767 0.8247 1.0021 0.093 Uiso 1 1 calc R . .
H16B H 1.0653 0.9146 0.9091 0.093 Uiso 1 1 calc R . .
H16C H 1.2408 0.8657 0.9515 0.093 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.447(3) . ?
S1 O1 1.447(3) . ?
S1 N3 1.589(3) . ?
S1 C2 1.764(4) . ?
N5 C9 1.337(6) . ?
N5 C4 1.362(5) . ?
C1 C3 1.383(6) . ?
C1 C2 1.391(6) . ?
C1 H1 0.9300 . ?
N4 C12 1.331(6) . ?
N4 C4 1.331(6) . ?
C2 C5 1.385(6) . ?
C3 C8 1.387(6) . ?
C3 H3 0.9300 . ?
N2 C10 1.327(7) . ?
N2 C11 1.338(6) . ?
N2 H2 0.8600 . ?
C4 N3 1.378(6) . ?
N6 C8 1.397(5) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
C5 C7 1.390(6) . ?
C5 H5 0.9300 . ?
C6 N1 1.321(6) . ?
C6 C13 1.409(7) . ?
C6 C15 1.429(6) . ?
C7 C8 1.379(6) . ?
C7 H7 0.9300 . ?
C9 C14 1.384(8) . ?
C9 C16 1.494(6) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C10 C15 1.314(7) . ?
C10 H10 0.9300 . ?
C11 C13 1.339(7) . ?
C11 H11 0.9300 . ?
C12 C14 1.371(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O2 S1 O1 114.9(2) . . ?
O2 S1 N3 105.1(2) . . ?
O1 S1 N3 113.57(19) . . ?
O2 S1 C2 106.8(2) . . ?
O1 S1 C2 107.6(2) . . ?
N3 S1 C2 108.50(19) . . ?
C9 N5 C4 116.3(5) . . ?
C3 C1 C2 120.3(4) . . ?
C3 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C12 N4 C4 115.6(4) . . ?
C5 C2 C1 119.4(4) . . ?
C5 C2 S1 120.4(3) . . ?
C1 C2 S1 120.2(3) . . ?
C1 C3 C8 120.4(4) . . ?
C1 C3 H3 119.8 . . ?
C8 C3 H3 119.8 . . ?
C10 N2 C11 120.4(5) . . ?
C10 N2 H2 119.8 . . ?
C11 N2 H2 119.8 . . ?
N4 C4 N5 125.7(4) . . ?
N4 C4 N3 122.6(4) . . ?
N5 C4 N3 111.6(5) . . ?
C4 N3 S1 121.5(3) . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C2 C5 C7 119.9(4) . . ?
C2 C5 H5 120.0 . . ?
C7 C5 H5 120.0 . . ?
N1 C6 C13 122.4(5) . . ?
N1 C6 C15 123.2(5) . . ?
C13 C6 C15 114.4(5) . . ?
C8 C7 C5 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
C5 C7 H7 119.6 . . ?
C7 C8 C3 119.3(4) . . ?
C7 C8 N6 120.2(4) . . ?
C3 C8 N6 120.6(4) . . ?
N5 C9 C14 121.9(4) . . ?
N5 C9 C16 116.7(6) . . ?
C14 C9 C16 121.4(5) . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C15 C10 N2 121.4(5) . . ?
C15 C10 H10 119.3 . . ?
N2 C10 H10 119.3 . . ?
N2 C11 C13 121.4(5) . . ?
N2 C11 H11 119.3 . . ?
C13 C11 H11 119.3 . . ?
N4 C12 C14 124.0(6) . . ?
N4 C12 H12 118.0 . . ?
C14 C12 H12 118.0 . . ?
C11 C13 C6 120.7(5) . . ?
C11 C13 H13 119.6 . . ?
C6 C13 H13 119.6 . . ?
C12 C14 C9 116.4(5) . . ?
C12 C14 H14 121.8 . . ?
C9 C14 H14 121.8 . . ?
C10 C15 C6 121.7(5) . . ?
C10 C15 H15 119.2 . . ?
C6 C15 H15 119.2 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C3 C1 C2 C5 -0.5(7) . . . . ?
C3 C1 C2 S1 176.1(4) . . . . ?
O2 S1 C2 C5 95.5(4) . . . . ?
O1 S1 C2 C5 -140.6(4) . . . . ?
N3 S1 C2 C5 -17.4(5) . . . . ?
O2 S1 C2 C1 -81.1(4) . . . . ?
O1 S1 C2 C1 42.8(4) . . . . ?
N3 S1 C2 C1 166.1(4) . . . . ?
C2 C1 C3 C8 1.8(7) . . . . ?
C12 N4 C4 N5 0.4(6) . . . . ?
C12 N4 C4 N3 -179.5(4) . . . . ?
C9 N5 C4 N4 -1.1(6) . . . . ?
C9 N5 C4 N3 178.8(3) . . . . ?
N4 C4 N3 S1 14.1(5) . . . . ?
N5 C4 N3 S1 -165.8(3) . . . . ?
O2 S1 N3 C4 172.3(3) . . . . ?
O1 S1 N3 C4 45.9(4) . . . . ?
C2 S1 N3 C4 -73.7(4) . . . . ?
C1 C2 C5 C7 -1.5(7) . . . . ?
S1 C2 C5 C7 -178.0(4) . . . . ?
C2 C5 C7 C8 2.1(8) . . . . ?
C5 C7 C8 C3 -0.8(8) . . . . ?
C5 C7 C8 N6 177.7(5) . . . . ?
C1 C3 C8 C7 -1.2(8) . . . . ?
C1 C3 C8 N6 -179.7(4) . . . . ?
C4 N5 C9 C14 0.8(6) . . . . ?
C4 N5 C9 C16 -179.8(4) . . . . ?
C11 N2 C10 C15 -2.1(7) . . . . ?
C10 N2 C11 C13 0.8(6) . . . . ?
C4 N4 C12 C14 0.6(6) . . . . ?
N2 C11 C13 C6 -0.4(7) . . . . ?
N1 C6 C13 C11 179.8(4) . . . . ?
C15 C6 C13 C11 1.2(6) . . . . ?
N4 C12 C14 C9 -0.8(7) . . . . ?
N5 C9 C14 C12 0.0(7) . . . . ?
C16 C9 C14 C12 -179.4(4) . . . . ?
N2 C10 C15 C6 3.0(7) . . . . ?
N1 C6 C15 C10 179.0(4) . . . . ?
C13 C6 C15 C10 -2.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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_jmpy5m
_database_code_depnum_ccdc_archive 'CCDC 1510567'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
;  
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C11 H11 N4 O2 S), C4 H12 N2'
_chemical_formula_sum            'C26 H34 N10 O4 S2'
_chemical_formula_weight         614.75

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                   5.9301(9)
_cell_length_b                   13.886(2)
_cell_length_c                   18.557(3)
_cell_angle_alpha                86.989(3)
_cell_angle_beta                 81.358(3)
_cell_angle_gamma                82.556(3)
_cell_volume                     1497.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2023
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      23.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .41
_exptl_crystal_size_mid          .32
_exptl_crystal_size_min          .17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .854
_exptl_absorpt_correction_T_max  .980
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            6405
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5251
_reflns_number_gt                3730
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1302P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5251
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1850
_refine_ls_wR_factor_gt          0.1468
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.26730(12) 0.68267(5) 0.11614(4) 0.0396(3) Uani 1 1 d . . .
O4 O 0.0224(3) 0.67748(15) 0.12447(11) 0.0464(5) Uani 1 1 d . . .
N9 N 0.3908(4) 0.67642(18) 0.03463(13) 0.0435(6) Uani 1 1 d . . .
O3 O 0.3905(4) 0.60592(15) 0.15553(12) 0.0524(6) Uani 1 1 d . . .
C1 C 0.3064(5) 0.7934(2) 0.15064(15) 0.0386(7) Uani 1 1 d . . .
C2 C 0.3026(5) 0.7333(2) -0.02078(16) 0.0429(7) Uani 1 1 d . . .
N7 N 0.1151(5) 0.7971(2) -0.00760(13) 0.0509(7) Uani 1 1 d . . .
N8 N 0.4215(5) 0.7132(2) -0.08764(15) 0.0600(8) Uani 1 1 d . . .
C3 C 0.3872(6) 0.9636(2) 0.21024(16) 0.0474(8) Uani 1 1 d . . .
C4 C 0.1362(5) 0.8442(2) 0.19858(16) 0.0453(7) Uani 1 1 d . . .
H4 H -0.0059 0.8214 0.2109 0.054 Uiso 1 1 calc R . .
C5 C 0.5569(6) 0.9118(2) 0.16248(18) 0.0501(8) Uani 1 1 d . . .
H5 H 0.6991 0.9344 0.1501 0.060 Uiso 1 1 calc R . .
N10 N 0.4271(6) 1.0476(2) 0.23785(18) 0.0727(9) Uani 1 1 d . . .
H10A H 0.5579 1.0688 0.2258 0.087 Uiso 1 1 calc R . .
H10B H 0.3214 1.0794 0.2674 0.087 Uiso 1 1 calc R . .
C6 C 0.1765(6) 0.9278(2) 0.22791(17) 0.0512(8) Uani 1 1 d . . .
H6 H 0.0611 0.9612 0.2602 0.061 Uiso 1 1 calc R . .
C7 C 0.0331(6) 0.8429(3) -0.06520(18) 0.0590(9) Uani 1 1 d . . .
C8 C 0.5181(5) 0.8279(2) 0.13329(17) 0.0471(7) Uani 1 1 d . . .
H8 H 0.6342 0.7939 0.1017 0.057 Uiso 1 1 calc R . .
C9 C 0.1356(8) 0.8242(3) -0.1349(2) 0.0720(11) Uani 1 1 d . . .
H9 H 0.0745 0.8543 -0.1749 0.086 Uiso 1 1 calc R . .
C10 C 0.3299(8) 0.7601(3) -0.14351(19) 0.0752(12) Uani 1 1 d . . .
H10 H 0.4036 0.7480 -0.1906 0.090 Uiso 1 1 calc R . .
C11 C -0.1799(8) 0.9146(4) -0.0493(3) 0.0965(16) Uani 1 1 d . . .
H11A H -0.2541 0.9028 -0.0006 0.145 Uiso 1 1 calc R . .
H11B H -0.2830 0.9074 -0.0834 0.145 Uiso 1 1 calc R . .
H11C H -0.1384 0.9795 -0.0539 0.145 Uiso 1 1 calc R . .
S2 S 0.92729(14) 0.19119(6) 0.36162(4) 0.0461(3) Uani 1 1 d . . .
O1 O 0.8159(4) 0.13024(17) 0.32118(12) 0.0592(6) Uani 1 1 d . . .
O2 O 1.1744(4) 0.16859(17) 0.35337(12) 0.0586(6) Uani 1 1 d . . .
N5 N 0.8078(5) 0.18177(19) 0.44310(13) 0.0487(7) Uani 1 1 d . . .
N12 N 0.7330(5) 0.5974(2) 0.25435(15) 0.0599(8) Uani 1 1 d . . .
H12A H 0.8431 0.6283 0.2335 0.072 Uiso 1 1 calc R . .
H12B H 0.5945 0.6262 0.2611 0.072 Uiso 1 1 calc R . .
N6 N 0.7336(6) 0.2195(2) 0.56271(15) 0.0640(8) Uani 1 1 d . . .
C12 C 0.7785(5) 0.5015(2) 0.27703(16) 0.0457(8) Uani 1 1 d . . .
C13 C 0.6506(5) 0.3579(2) 0.33843(17) 0.0471(8) Uani 1 1 d . . .
H13 H 0.5318 0.3253 0.3623 0.057 Uiso 1 1 calc R . .
C14 C 1.0002(6) 0.4539(3) 0.26662(17) 0.0546(9) Uani 1 1 d . . .
H14 H 1.1189 0.4856 0.2416 0.066 Uiso 1 1 calc R . .
N11 N 1.0272(5) 0.2923(2) 0.48455(14) 0.0532(7) Uani 1 1 d . . .
C15 C 0.8725(5) 0.3109(2) 0.32903(15) 0.0413(7) Uani 1 1 d . . .
C16 C 0.8606(5) 0.2345(2) 0.49836(16) 0.0449(7) Uani 1 1 d . . .
C17 C 1.0668(7) 0.3413(3) 0.5409(2) 0.0622(10) Uani 1 1 d . . .
C18 C 0.6027(6) 0.4514(3) 0.31328(17) 0.0517(8) Uani 1 1 d . . .
H18 H 0.4522 0.4819 0.3203 0.062 Uiso 1 1 calc R . .
C19 C 1.0462(6) 0.3603(3) 0.29297(18) 0.0541(9) Uani 1 1 d . . .
H19 H 1.1965 0.3297 0.2864 0.065 Uiso 1 1 calc R . .
C20 C 0.9440(8) 0.3300(3) 0.6087(2) 0.0802(12) Uani 1 1 d . . .
H20 H 0.9706 0.3638 0.6479 0.096 Uiso 1 1 calc R . .
C21 C 1.2485(8) 0.4081(3) 0.5251(3) 0.0881(13) Uani 1 1 d . . .
H21A H 1.3974 0.3705 0.5189 0.132 Uiso 1 1 calc R . .
H21B H 1.2369 0.4505 0.5651 0.132 Uiso 1 1 calc R . .
H21C H 1.2278 0.4461 0.4814 0.132 Uiso 1 1 calc R . .
C22 C 0.7813(8) 0.2678(3) 0.6170(2) 0.0775(12) Uani 1 1 d . . .
H22 H 0.6996 0.2588 0.6632 0.093 Uiso 1 1 calc R . .
N1 N 0.8344(4) 0.58268(17) 0.01965(14) 0.0445(6) Uani 1 1 d . . .
H1A H 0.6900 0.6130 0.0221 0.053 Uiso 1 1 calc R . .
H1B H 0.9189 0.6218 0.0384 0.053 Uiso 1 1 calc R . .
C23 C 0.9298(5) 0.5658(2) -0.05705(17) 0.0483(8) Uani 1 1 d . . .
H23A H 0.9377 0.6278 -0.0834 0.058 Uiso 1 1 calc R . .
H23B H 0.8290 0.5300 -0.0789 0.058 Uiso 1 1 calc R . .
C24 C 0.8325(5) 0.4907(2) 0.06361(18) 0.0487(8) Uani 1 1 d . . .
H24A H 0.7273 0.4516 0.0471 0.058 Uiso 1 1 calc R . .
H24B H 0.7784 0.5049 0.1144 0.058 Uiso 1 1 calc R . .
N3 N 0.4328(5) 0.0858(2) 0.45996(15) 0.0558(7) Uani 1 1 d . . .
H3A H 0.5587 0.1165 0.4568 0.067 Uiso 1 1 calc R . .
H3B H 0.3295 0.1232 0.4364 0.067 Uiso 1 1 calc R . .
C25 C 0.3356(6) 0.0734(3) 0.5371(2) 0.0609(9) Uani 1 1 d . . .
H25A H 0.1931 0.0450 0.5408 0.073 Uiso 1 1 calc R . .
H25B H 0.3025 0.1362 0.5596 0.073 Uiso 1 1 calc R . .
C26 C 0.4952(6) -0.0084(3) 0.42424(19) 0.0611(9) Uani 1 1 d . . .
H26A H 0.5616 0.0024 0.3739 0.073 Uiso 1 1 calc R . .
H26B H 0.3580 -0.0397 0.4245 0.073 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.443(2) . ?
S1 O4 1.448(2) . ?
S1 N9 1.580(3) . ?
S1 C1 1.752(3) . ?
N9 C2 1.387(4) . ?
C1 C4 1.385(4) . ?
C1 C8 1.388(4) . ?
C2 N7 1.329(4) . ?
C2 N8 1.355(4) . ?
N7 C7 1.338(4) . ?
N8 C10 1.342(5) . ?
C3 N10 1.359(4) . ?
C3 C5 1.388(5) . ?
C3 C6 1.391(5) . ?
C4 C6 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C8 1.370(4) . ?
C5 H5 0.9300 . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
C6 H6 0.9300 . ?
C7 C9 1.367(5) . ?
C7 C11 1.505(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.357(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
S2 O1 1.441(2) . ?
S2 O2 1.445(2) . ?
S2 N5 1.577(3) . ?
S2 C15 1.746(3) . ?
N5 C16 1.385(4) . ?
N12 C12 1.380(4) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N6 C22 1.323(5) . ?
N6 C16 1.334(4) . ?
C12 C14 1.384(5) . ?
C12 C18 1.397(4) . ?
C13 C18 1.365(4) . ?
C13 C15 1.381(4) . ?
C13 H13 0.9300 . ?
C14 C19 1.373(5) . ?
C14 H14 0.9300 . ?
N11 C16 1.339(4) . ?
N11 C17 1.342(4) . ?
C15 C19 1.381(4) . ?
C17 C20 1.367(6) . ?
C17 C21 1.498(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C22 1.363(6) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?
N1 C23 1.469(4) . ?
N1 C24 1.479(4) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
C23 C24 1.513(4) 2_765 ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C23 1.513(4) 2_765 ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
N3 C25 1.470(5) . ?
N3 C26 1.476(5) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
C25 C26 1.501(4) 2_656 ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C25 1.501(4) 2_656 ?
C26 H26A 0.9700 . ?
C26 H26B 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
O3 S1 O4 113.46(13) . . ?
O3 S1 N9 105.05(13) . . ?
O4 S1 N9 113.97(12) . . ?
O3 S1 C1 107.71(12) . . ?
O4 S1 C1 107.54(13) . . ?
N9 S1 C1 108.89(13) . . ?
C2 N9 S1 121.1(2) . . ?
C4 C1 C8 119.2(3) . . ?
C4 C1 S1 121.5(2) . . ?
C8 C1 S1 119.2(2) . . ?
N7 C2 N8 125.3(3) . . ?
N7 C2 N9 121.8(3) . . ?
N8 C2 N9 112.9(3) . . ?
C2 N7 C7 117.3(3) . . ?
C10 N8 C2 114.9(3) . . ?
N10 C3 C5 120.3(3) . . ?
N10 C3 C6 121.5(3) . . ?
C5 C3 C6 118.2(3) . . ?
C6 C4 C1 120.2(3) . . ?
C6 C4 H4 119.9 . . ?
C1 C4 H4 119.9 . . ?
C8 C5 C3 121.0(3) . . ?
C8 C5 H5 119.5 . . ?
C3 C5 H5 119.5 . . ?
C3 N10 H10A 120.0 . . ?
C3 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C4 C6 C3 121.1(3) . . ?
C4 C6 H6 119.5 . . ?
C3 C6 H6 119.5 . . ?
N7 C7 C9 121.5(4) . . ?
N7 C7 C11 116.6(3) . . ?
C9 C7 C11 121.9(3) . . ?
C5 C8 C1 120.4(3) . . ?
C5 C8 H8 119.8 . . ?
C1 C8 H8 119.8 . . ?
C10 C9 C7 117.4(3) . . ?
C10 C9 H9 121.3 . . ?
C7 C9 H9 121.3 . . ?
N8 C10 C9 123.5(3) . . ?
N8 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 S2 O2 114.17(15) . . ?
O1 S2 N5 105.29(14) . . ?
O2 S2 N5 113.24(13) . . ?
O1 S2 C15 108.22(13) . . ?
O2 S2 C15 106.25(14) . . ?
N5 S2 C15 109.57(14) . . ?
C16 N5 S2 122.5(2) . . ?
C12 N12 H12A 120.0 . . ?
C12 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C22 N6 C16 115.0(3) . . ?
N12 C12 C14 120.8(3) . . ?
N12 C12 C18 120.7(3) . . ?
C14 C12 C18 118.5(3) . . ?
C18 C13 C15 121.1(3) . . ?
C18 C13 H13 119.4 . . ?
C15 C13 H13 119.4 . . ?
C19 C14 C12 120.5(3) . . ?
C19 C14 H14 119.8 . . ?
C12 C14 H14 119.8 . . ?
C16 N11 C17 116.5(3) . . ?
C19 C15 C13 118.6(3) . . ?
C19 C15 S2 121.5(2) . . ?
C13 C15 S2 119.9(2) . . ?
N6 C16 N11 126.5(3) . . ?
N6 C16 N5 113.3(3) . . ?
N11 C16 N5 120.2(3) . . ?
N11 C17 C20 120.6(4) . . ?
N11 C17 C21 116.6(4) . . ?
C20 C17 C21 122.7(4) . . ?
C13 C18 C12 120.4(3) . . ?
C13 C18 H18 119.8 . . ?
C12 C18 H18 119.8 . . ?
C14 C19 C15 121.0(3) . . ?
C14 C19 H19 119.5 . . ?
C15 C19 H19 119.5 . . ?
C22 C20 C17 118.0(3) . . ?
C22 C20 H20 121.0 . . ?
C17 C20 H20 121.0 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 C20 123.4(4) . . ?
N6 C22 H22 118.3 . . ?
C20 C22 H22 118.3 . . ?
C23 N1 C24 111.7(2) . . ?
C23 N1 H1A 109.3 . . ?
C24 N1 H1A 109.3 . . ?
C23 N1 H1B 109.3 . . ?
C24 N1 H1B 109.3 . . ?
H1A N1 H1B 107.9 . . ?
N1 C23 C24 111.2(2) . 2_765 ?
N1 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 2_765 . ?
N1 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 2_765 . ?
H23A C23 H23B 108.0 . . ?
N1 C24 C23 111.0(3) . 2_765 ?
N1 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 2_765 . ?
N1 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 2_765 . ?
H24A C24 H24B 108.0 . . ?
C25 N3 C26 111.7(3) . . ?
C25 N3 H3A 109.3 . . ?
C26 N3 H3A 109.3 . . ?
C25 N3 H3B 109.3 . . ?
C26 N3 H3B 109.3 . . ?
H3A N3 H3B 107.9 . . ?
N3 C25 C26 109.3(3) . 2_656 ?
N3 C25 H25A 109.8 . . ?
C26 C25 H25A 109.8 2_656 . ?
N3 C25 H25B 109.8 . . ?
C26 C25 H25B 109.8 2_656 . ?
H25A C25 H25B 108.3 . . ?
N3 C26 C25 110.8(3) . 2_656 ?
N3 C26 H26A 109.5 . . ?
C25 C26 H26A 109.5 2_656 . ?
N3 C26 H26B 109.5 . . ?
C25 C26 H26B 109.5 2_656 . ?
H26A C26 H26B 108.1 . . ?

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
O3 S1 N9 C2 173.2(2) . . . . ?
O4 S1 N9 C2 48.4(2) . . . . ?
C1 S1 N9 C2 -71.7(2) . . . . ?
O3 S1 C1 C4 -102.5(3) . . . . ?
O4 S1 C1 C4 20.2(3) . . . . ?
N9 S1 C1 C4 144.1(2) . . . . ?
O3 S1 C1 C8 73.3(3) . . . . ?
O4 S1 C1 C8 -164.1(2) . . . . ?
N9 S1 C1 C8 -40.1(3) . . . . ?
S1 N9 C2 N7 1.8(4) . . . . ?
S1 N9 C2 N8 -175.5(2) . . . . ?
N8 C2 N7 C7 2.1(5) . . . . ?
N9 C2 N7 C7 -174.9(3) . . . . ?
N7 C2 N8 C10 -3.1(5) . . . . ?
N9 C2 N8 C10 174.1(3) . . . . ?
C8 C1 C4 C6 0.5(4) . . . . ?
S1 C1 C4 C6 176.3(2) . . . . ?
N10 C3 C5 C8 -178.9(3) . . . . ?
C6 C3 C5 C8 0.2(5) . . . . ?
C1 C4 C6 C3 0.2(5) . . . . ?
N10 C3 C6 C4 178.6(3) . . . . ?
C5 C3 C6 C4 -0.6(4) . . . . ?
C2 N7 C7 C9 0.9(5) . . . . ?
C2 N7 C7 C11 179.8(3) . . . . ?
C3 C5 C8 C1 0.5(5) . . . . ?
C4 C1 C8 C5 -0.8(4) . . . . ?
S1 C1 C8 C5 -176.7(2) . . . . ?
N7 C7 C9 C10 -2.7(6) . . . . ?
C11 C7 C9 C10 178.5(4) . . . . ?
C2 N8 C10 C9 1.1(5) . . . . ?
C7 C9 C10 N8 1.6(6) . . . . ?
O1 S2 N5 C16 -176.4(2) . . . . ?
O2 S2 N5 C16 58.2(3) . . . . ?
C15 S2 N5 C16 -60.3(3) . . . . ?
N12 C12 C14 C19 176.3(3) . . . . ?
C18 C12 C14 C19 -1.5(5) . . . . ?
C18 C13 C15 C19 -0.5(4) . . . . ?
C18 C13 C15 S2 -179.8(2) . . . . ?
O1 S2 C15 C19 -113.9(3) . . . . ?
O2 S2 C15 C19 9.1(3) . . . . ?
N5 S2 C15 C19 131.8(3) . . . . ?
O1 S2 C15 C13 65.4(3) . . . . ?
O2 S2 C15 C13 -171.6(2) . . . . ?
N5 S2 C15 C13 -48.9(3) . . . . ?
C22 N6 C16 N11 0.1(5) . . . . ?
C22 N6 C16 N5 179.2(3) . . . . ?
C17 N11 C16 N6 -1.3(5) . . . . ?
C17 N11 C16 N5 179.6(3) . . . . ?
S2 N5 C16 N6 177.2(2) . . . . ?
S2 N5 C16 N11 -3.7(4) . . . . ?
C16 N11 C17 C20 1.2(5) . . . . ?
C16 N11 C17 C21 -178.4(3) . . . . ?
C15 C13 C18 C12 0.3(5) . . . . ?
N12 C12 C18 C13 -177.1(3) . . . . ?
C14 C12 C18 C13 0.7(5) . . . . ?
C12 C14 C19 C15 1.3(5) . . . . ?
C13 C15 C19 C14 -0.3(5) . . . . ?
S2 C15 C19 C14 179.0(2) . . . . ?
N11 C17 C20 C22 0.0(6) . . . . ?
C21 C17 C20 C22 179.6(4) . . . . ?
C16 N6 C22 C20 1.3(6) . . . . ?
C17 C20 C22 N6 -1.4(7) . . . . ?
C24 N1 C23 C24 -55.4(4) . . . 2_765 ?
C23 N1 C24 C23 55.3(3) . . . 2_765 ?
C26 N3 C25 C26 57.1(4) . . . 2_656 ?
C25 N3 C26 C25 -57.9(4) . . . 2_656 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.128
####################################################################### 
# 
# 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_dv2acm
_database_code_depnum_ccdc_archive 'CCDC 1500514'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
;  
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H10 N3 O3 S), 2(C5 H7 N2), H2 O'
_chemical_formula_sum            'C30 H36 N10 O7 S2'
_chemical_formula_weight         712.81

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                   10.2001(18)
_cell_length_b                   11.201(2)
_cell_length_c                   15.778(3)
_cell_angle_alpha                106.698(3)
_cell_angle_beta                 91.809(3)
_cell_angle_gamma                101.329(4)
_cell_volume                     1685.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1657
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      22.60

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .47
_exptl_crystal_size_mid          .36
_exptl_crystal_size_min          .13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .860
_exptl_absorpt_correction_T_max  .995
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            8936
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5934
_reflns_number_gt                3991
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0725P)²+0.0495P] 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         5934
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1710(3) 0.6830(3) 0.96956(19) 0.0347(7) Uani 1 1 d . . .
C2 C 0.4979(3) 0.5867(3) 0.8408(2) 0.0401(7) Uani 1 1 d . . .
H2 H 0.5168 0.5346 0.8740 0.048 Uiso 1 1 calc R . .
C3 C 0.4522(3) 0.6951(3) 0.88140(19) 0.0353(7) Uani 1 1 d . . .
C4 C 0.0413(3) 0.7091(3) 0.9820(2) 0.0425(8) Uani 1 1 d . . .
H4 H 0.0206 0.7830 1.0187 0.051 Uiso 1 1 calc R . .
C5 C 0.4221(3) 0.7715(3) 0.8314(2) 0.0438(8) Uani 1 1 d . . .
H5 H 0.3921 0.8454 0.8585 0.053 Uiso 1 1 calc R . .
C6 C 0.4831(3) 0.6287(3) 0.7001(2) 0.0451(8) Uani 1 1 d . . .
C7 C -0.0442(3) 0.6074(3) 0.9310(2) 0.0418(8) Uani 1 1 d . . .
C8 C 0.4363(3) 0.7382(3) 0.7422(2) 0.0458(8) Uani 1 1 d . . .
H8 H 0.4146 0.7893 0.7090 0.055 Uiso 1 1 calc R . .
C9 C 0.5158(3) 0.5549(3) 0.7520(2) 0.0454(8) Uani 1 1 d . . .
H9 H 0.5502 0.4833 0.7260 0.054 Uiso 1 1 calc R . .
C10 C -0.1920(3) 0.5755(3) 0.9093(2) 0.0572(9) Uani 1 1 d . . .
H10A H -0.2120 0.5565 0.8464 0.086 Uiso 1 1 calc R . .
H10B H -0.2290 0.6469 0.9399 0.086 Uiso 1 1 calc R . .
H10C H -0.2307 0.5026 0.9276 0.086 Uiso 1 1 calc R . .
C11 C -0.0077(3) 0.6942(3) 0.47173(19) 0.0381(7) Uani 1 1 d . . .
C12 C 0.2693(3) 0.7760(3) 0.3946(2) 0.0384(7) Uani 1 1 d . . .
C13 C -0.2064(3) 0.7407(3) 0.4616(2) 0.0448(8) Uani 1 1 d . . .
C14 C 0.3146(3) 0.8995(3) 0.2646(2) 0.0499(9) Uani 1 1 d . . .
C15 C -0.1458(3) 0.6427(3) 0.4405(2) 0.0466(8) Uani 1 1 d . . .
H15 H -0.1854 0.5578 0.4114 0.056 Uiso 1 1 calc R . .
C16 C 0.3344(4) 0.9019(3) 0.4177(2) 0.0576(9) Uani 1 1 d . . .
H16 H 0.3632 0.9464 0.4769 0.069 Uiso 1 1 calc R . .
C17 C 0.2272(4) 0.7130(3) 0.3065(2) 0.0537(9) Uani 1 1 d . . .
H17 H 0.1828 0.6277 0.2903 0.064 Uiso 1 1 calc R . .
C18 C 0.2490(4) 0.7726(3) 0.2423(2) 0.0595(10) Uani 1 1 d . . .
H18 H 0.2197 0.7276 0.1832 0.071 Uiso 1 1 calc R . .
C19 C 0.3571(4) 0.9627(3) 0.3529(2) 0.0665(11) Uani 1 1 d . . .
H19 H 0.4019 1.0478 0.3692 0.080 Uiso 1 1 calc R . .
C20 C -0.3470(3) 0.7546(3) 0.4449(3) 0.0651(10) Uani 1 1 d . . .
H20A H -0.3951 0.6806 0.3993 0.098 Uiso 1 1 calc R . .
H20B H -0.3451 0.8292 0.4262 0.098 Uiso 1 1 calc R . .
H20C H -0.3909 0.7630 0.4986 0.098 Uiso 1 1 calc R . .
C21 C 0.7610(3) 0.7645(3) 0.1942(2) 0.0417(8) Uani 1 1 d . . .
C22 C 0.7432(4) 0.9647(3) 0.2929(2) 0.0573(9) Uani 1 1 d . . .
H22 H 0.6958 1.0292 0.3109 0.069 Uiso 1 1 calc R . .
C23 C 0.6921(3) 0.8631(3) 0.2218(2) 0.0530(9) Uani 1 1 d . . .
H23 H 0.6111 0.8588 0.1912 0.064 Uiso 1 1 calc R . .
C24 C 0.8840(3) 0.7793(3) 0.2424(2) 0.0508(9) Uani 1 1 d . . .
H24 H 0.9341 0.7167 0.2260 0.061 Uiso 1 1 calc R . .
C25 C 0.9301(4) 0.8838(4) 0.3122(2) 0.0561(9) Uani 1 1 d . . .
H25 H 1.0123 0.8927 0.3431 0.067 Uiso 1 1 calc R . .
C26 C -0.0778(3) 0.2189(3) 0.2189(2) 0.0516(9) Uani 1 1 d . . .
H26 H -0.1602 0.1852 0.1851 0.062 Uiso 1 1 calc R . .
C27 C 0.0295(3) 0.1598(3) 0.1968(2) 0.0466(8) Uani 1 1 d . . .
C28 C 0.1554(4) 0.3205(3) 0.3224(3) 0.0626(10) Uani 1 1 d . . .
H28 H 0.2357 0.3555 0.3585 0.075 Uiso 1 1 calc R . .
C29 C 0.1463(4) 0.2141(4) 0.2533(3) 0.0707(12) Uani 1 1 d . . .
H29 H 0.2201 0.1763 0.2434 0.085 Uiso 1 1 calc R . .
C30 C -0.0635(4) 0.3242(3) 0.2886(2) 0.0599(10) Uani 1 1 d . . .
H30 H -0.1366 0.3624 0.3018 0.072 Uiso 1 1 calc R . .
N1 N 0.3339(3) 0.9604(3) 0.2006(2) 0.0749(10) Uani 1 1 d . . .
H1A H 0.3732 1.0397 0.2151 0.090 Uiso 1 1 calc R . .
H1B H 0.3066 0.9193 0.1459 0.090 Uiso 1 1 calc R . .
N2 N 0.5006(3) 0.5983(3) 0.61085(18) 0.0661(9) Uani 1 1 d . . .
H2A H 0.5324 0.5325 0.5859 0.079 Uiso 1 1 calc R . .
H2B H 0.4798 0.6451 0.5801 0.079 Uiso 1 1 calc R . .
N3 N 0.0897(2) 0.6240(2) 0.46112(16) 0.0401(6) Uani 1 1 d . . .
N4 N 0.2871(2) 0.7711(2) 1.00839(16) 0.0382(6) Uani 1 1 d . . .
N5 N 0.0117(3) 0.8185(2) 0.51143(18) 0.0488(7) Uani 1 1 d . . .
N6 N 0.1626(2) 0.5681(2) 0.91449(19) 0.0484(7) Uani 1 1 d . . .
N7 N 0.0520(3) 0.3758(2) 0.33959(18) 0.0503(7) Uani 1 1 d . . .
H7 H 0.0592 0.4444 0.3832 0.060 Uiso 1 1 calc R . .
N8 N 0.8597(3) 0.9751(3) 0.33791(18) 0.0571(8) Uani 1 1 d . . .
H8A H 0.8896 1.0404 0.3834 0.069 Uiso 1 1 calc R . .
N9 N 0.7123(3) 0.6626(2) 0.12566(18) 0.0526(7) Uani 1 1 d . . .
H9A H 0.6367 0.6561 0.0971 0.063 Uiso 1 1 calc R . .
H9B H 0.7562 0.6028 0.1097 0.063 Uiso 1 1 calc R . .
N10 N 0.0181(3) 0.0580(3) 0.1258(2) 0.0710(9) Uani 1 1 d . . .
H10D H 0.0855 0.0225 0.1131 0.085 Uiso 1 1 calc R . .
H10E H -0.0565 0.0277 0.0927 0.085 Uiso 1 1 calc R . .
O1 O 0.2862(2) 0.7864(2) 0.56106(14) 0.0533(6) Uani 1 1 d . . .
O2 O 0.3160(2) 0.59198(19) 0.45194(14) 0.0504(6) Uani 1 1 d . . .
O3 O 0.5247(2) 0.8542(2) 1.03889(14) 0.0520(6) Uani 1 1 d . . .
O4 O 0.4452(2) 0.6288(2) 1.02480(14) 0.0494(6) Uani 1 1 d . . .
O5 O 0.2321(3) 0.0059(3) 0.99511(19) 0.0617(7) Uani 1 1 d . . .
O6 O 0.0223(2) 0.5185(2) 0.88856(15) 0.0517(6) Uani 1 1 d . . .
O7 O -0.1171(2) 0.8490(2) 0.50518(15) 0.0511(6) Uani 1 1 d . . .
S1 S 0.42887(7) 0.73630(7) 0.99526(5) 0.0381(2) Uani 1 1 d . . .
S2 S 0.24243(8) 0.69361(7) 0.47481(5) 0.0404(2) Uani 1 1 d . . .
H2W H 0.299(4) 0.060(4) 0.989(3) 0.083(15) Uiso 1 1 d . . .
H1W H 0.258(4) -0.062(5) 0.997(3) 0.113(19) 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
C1 N6 1.315(4) . ?
C1 N4 1.378(4) . ?
C1 C4 1.418(4) . ?
C2 C9 1.371(4) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C5 1.387(4) . ?
C3 S1 1.758(3) . ?
C4 C7 1.321(4) . ?
C4 H4 0.9300 . ?
C5 C8 1.369(4) . ?
C5 H5 0.9300 . ?
C6 N2 1.377(4) . ?
C6 C9 1.395(4) . ?
C6 C8 1.398(4) . ?
C7 O6 1.346(4) . ?
C7 C10 1.485(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N5 1.324(4) . ?
C11 N3 1.369(4) . ?
C11 C15 1.426(4) . ?
C12 C16 1.373(4) . ?
C12 C17 1.376(4) . ?
C12 S2 1.767(3) . ?
C13 C15 1.329(4) . ?
C13 O7 1.349(4) . ?
C13 C20 1.496(4) . ?
C14 N1 1.372(4) . ?
C14 C19 1.380(5) . ?
C14 C18 1.384(4) . ?
C15 H15 0.9300 . ?
C16 C19 1.383(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N9 1.325(4) . ?
C21 C23 1.397(4) . ?
C21 C24 1.402(4) . ?
C22 N8 1.332(4) . ?
C22 C23 1.349(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.347(5) . ?
C24 H24 0.9300 . ?
C25 N8 1.340(4) . ?
C25 H25 0.9300 . ?
C26 C30 1.341(5) . ?
C26 C27 1.391(4) . ?
C26 H26 0.9300 . ?
C27 N10 1.331(4) . ?
C27 C29 1.386(5) . ?
C28 N7 1.322(4) . ?
C28 C29 1.350(5) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 N7 1.332(4) . ?
C30 H30 0.9300 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 S2 1.577(2) . ?
N4 S1 1.574(2) . ?
N5 O7 1.429(3) . ?
N6 O6 1.430(3) . ?
N7 H7 0.8600 . ?
N8 H8A 0.8600 . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 H10D 0.8600 . ?
N10 H10E 0.8600 . ?
O1 S2 1.449(2) . ?
O2 S2 1.451(2) . ?
O3 S1 1.450(2) . ?
O4 S1 1.446(2) . ?
O5 H2W 0.85(4) . ?
O5 H1W 0.86(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
N6 C1 N4 126.7(3) . . ?
N6 C1 C4 110.5(3) . . ?
N4 C1 C4 122.8(3) . . ?
C9 C2 C3 120.6(3) . . ?
C9 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C5 119.6(3) . . ?
C2 C3 S1 120.8(2) . . ?
C5 C3 S1 119.6(2) . . ?
C7 C4 C1 106.1(3) . . ?
C7 C4 H4 127.0 . . ?
C1 C4 H4 127.0 . . ?
C8 C5 C3 120.0(3) . . ?
C8 C5 H5 120.0 . . ?
C3 C5 H5 120.0 . . ?
N2 C6 C9 121.5(3) . . ?
N2 C6 C8 120.5(3) . . ?
C9 C6 C8 117.9(3) . . ?
C4 C7 O6 110.2(3) . . ?
C4 C7 C10 133.7(3) . . ?
O6 C7 C10 116.0(3) . . ?
C5 C8 C6 121.1(3) . . ?
C5 C8 H8 119.5 . . ?
C6 C8 H8 119.5 . . ?
C2 C9 C6 120.8(3) . . ?
C2 C9 H9 119.6 . . ?
C6 C9 H9 119.6 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 N3 125.6(3) . . ?
N5 C11 C15 110.1(3) . . ?
N3 C11 C15 124.3(3) . . ?
C16 C12 C17 118.6(3) . . ?
C16 C12 S2 121.5(3) . . ?
C17 C12 S2 119.9(2) . . ?
C15 C13 O7 110.2(3) . . ?
C15 C13 C20 133.8(3) . . ?
O7 C13 C20 116.0(3) . . ?
N1 C14 C19 121.4(3) . . ?
N1 C14 C18 120.5(3) . . ?
C19 C14 C18 118.1(3) . . ?
C13 C15 C11 106.0(3) . . ?
C13 C15 H15 127.0 . . ?
C11 C15 H15 127.0 . . ?
C12 C16 C19 120.0(3) . . ?
C12 C16 H16 120.0 . . ?
C19 C16 H16 120.0 . . ?
C18 C17 C12 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
C17 C18 C14 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C14 C18 H18 119.8 . . ?
C14 C19 C16 121.3(3) . . ?
C14 C19 H19 119.3 . . ?
C16 C19 H19 119.3 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N9 C21 C23 121.4(3) . . ?
N9 C21 C24 121.9(3) . . ?
C23 C21 C24 116.7(3) . . ?
N8 C22 C23 121.9(3) . . ?
N8 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C21 120.0(3) . . ?
C22 C23 H23 120.0 . . ?
C21 C23 H23 120.0 . . ?
C25 C24 C21 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
C21 C24 H24 119.8 . . ?
N8 C25 C24 121.3(3) . . ?
N8 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C30 C26 C27 120.6(3) . . ?
C30 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
N10 C27 C29 123.4(3) . . ?
N10 C27 C26 121.2(3) . . ?
C29 C27 C26 115.4(3) . . ?
N7 C28 C29 121.1(3) . . ?
N7 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C28 C29 C27 121.5(3) . . ?
C28 C29 H29 119.2 . . ?
C27 C29 H29 119.2 . . ?
N7 C30 C26 122.0(3) . . ?
N7 C30 H30 119.0 . . ?
C26 C30 H30 119.0 . . ?
C14 N1 H1A 120.0 . . ?
C14 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C11 N3 S2 119.8(2) . . ?
C1 N4 S1 121.0(2) . . ?
C11 N5 O7 105.5(2) . . ?
C1 N6 O6 105.2(2) . . ?
C28 N7 C30 119.3(3) . . ?
C28 N7 H7 120.4 . . ?
C30 N7 H7 120.4 . . ?
C22 N8 C25 119.8(3) . . ?
C22 N8 H8A 120.1 . . ?
C25 N8 H8A 120.1 . . ?
C21 N9 H9A 120.0 . . ?
C21 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C27 N10 H10D 120.0 . . ?
C27 N10 H10E 120.0 . . ?
H10D N10 H10E 120.0 . . ?
H2W O5 H1W 109(4) . . ?
C7 O6 N6 108.0(2) . . ?
C13 O7 N5 108.1(2) . . ?
O4 S1 O3 114.67(13) . . ?
O4 S1 N4 114.09(13) . . ?
O3 S1 N4 104.89(13) . . ?
O4 S1 C3 106.55(13) . . ?
O3 S1 C3 107.42(13) . . ?
N4 S1 C3 108.99(13) . . ?
O1 S2 O2 114.35(13) . . ?
O1 S2 N3 115.26(13) . . ?
O2 S2 N3 105.23(13) . . ?
O1 S2 C12 107.15(14) . . ?
O2 S2 C12 106.95(13) . . ?
N3 S2 C12 107.44(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C2 C3 C5 1.1(4) . . . . ?
C9 C2 C3 S1 179.9(2) . . . . ?
N6 C1 C4 C7 -1.4(3) . . . . ?
N4 C1 C4 C7 176.1(3) . . . . ?
C2 C3 C5 C8 0.7(4) . . . . ?
S1 C3 C5 C8 -178.1(2) . . . . ?
C1 C4 C7 O6 0.9(3) . . . . ?
C1 C4 C7 C10 -175.9(3) . . . . ?
C3 C5 C8 C6 -1.0(5) . . . . ?
N2 C6 C8 C5 -178.1(3) . . . . ?
C9 C6 C8 C5 -0.5(5) . . . . ?
C3 C2 C9 C6 -2.6(5) . . . . ?
N2 C6 C9 C2 179.9(3) . . . . ?
C8 C6 C9 C2 2.3(5) . . . . ?
O7 C13 C15 C11 -1.3(4) . . . . ?
C20 C13 C15 C11 176.7(3) . . . . ?
N5 C11 C15 C13 1.1(4) . . . . ?
N3 C11 C15 C13 -178.5(3) . . . . ?
C17 C12 C16 C19 -0.4(5) . . . . ?
S2 C12 C16 C19 178.2(3) . . . . ?
C16 C12 C17 C18 0.2(5) . . . . ?
S2 C12 C17 C18 -178.4(3) . . . . ?
C12 C17 C18 C14 -0.2(6) . . . . ?
N1 C14 C18 C17 -178.5(3) . . . . ?
C19 C14 C18 C17 0.3(5) . . . . ?
N1 C14 C19 C16 178.3(3) . . . . ?
C18 C14 C19 C16 -0.5(6) . . . . ?
C12 C16 C19 C14 0.5(6) . . . . ?
N8 C22 C23 C21 0.7(6) . . . . ?
N9 C21 C23 C22 178.8(3) . . . . ?
C24 C21 C23 C22 -1.5(5) . . . . ?
N9 C21 C24 C25 -179.5(3) . . . . ?
C23 C21 C24 C25 0.8(5) . . . . ?
C21 C24 C25 N8 0.7(5) . . . . ?
C30 C26 C27 N10 -177.5(3) . . . . ?
C30 C26 C27 C29 2.6(5) . . . . ?
N7 C28 C29 C27 1.2(6) . . . . ?
N10 C27 C29 C28 177.2(4) . . . . ?
C26 C27 C29 C28 -2.9(6) . . . . ?
C27 C26 C30 N7 -0.5(6) . . . . ?
N5 C11 N3 S2 -15.7(4) . . . . ?
C15 C11 N3 S2 163.9(2) . . . . ?
N6 C1 N4 S1 -5.0(4) . . . . ?
C4 C1 N4 S1 177.9(2) . . . . ?
N3 C11 N5 O7 179.1(2) . . . . ?
C15 C11 N5 O7 -0.5(3) . . . . ?
N4 C1 N6 O6 -176.1(3) . . . . ?
C4 C1 N6 O6 1.3(3) . . . . ?
C29 C28 N7 C30 1.1(5) . . . . ?
C26 C30 N7 C28 -1.4(5) . . . . ?
C23 C22 N8 C25 0.8(5) . . . . ?
C24 C25 N8 C22 -1.5(5) . . . . ?
C4 C7 O6 N6 -0.2(3) . . . . ?
C10 C7 O6 N6 177.3(2) . . . . ?
C1 N6 O6 C7 -0.7(3) . . . . ?
C15 C13 O7 N5 1.0(3) . . . . ?
C20 C13 O7 N5 -177.4(3) . . . . ?
C11 N5 O7 C13 -0.2(3) . . . . ?
C1 N4 S1 O4 -58.4(3) . . . . ?
C1 N4 S1 O3 175.3(2) . . . . ?
C1 N4 S1 C3 60.5(2) . . . . ?
C2 C3 S1 O4 -8.8(3) . . . . ?
C5 C3 S1 O4 170.0(2) . . . . ?
C2 C3 S1 O3 114.5(2) . . . . ?
C5 C3 S1 O3 -66.7(3) . . . . ?
C2 C3 S1 N4 -132.4(2) . . . . ?
C5 C3 S1 N4 46.5(3) . . . . ?
C11 N3 S2 O1 57.3(3) . . . . ?
C11 N3 S2 O2 -175.7(2) . . . . ?
C11 N3 S2 C12 -62.0(3) . . . . ?
C16 C12 S2 O1 6.3(3) . . . . ?
C17 C12 S2 O1 -175.1(3) . . . . ?
C16 C12 S2 O2 -116.7(3) . . . . ?
C17 C12 S2 O2 61.8(3) . . . . ?
C16 C12 S2 N3 130.7(3) . . . . ?
C17 C12 S2 N3 -50.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053
