# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1407124'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 N3 O2, C7 H4 N O3 S'
_chemical_formula_sum            'C20 H16 N4 O5 S'
_chemical_formula_weight         424.43

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/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   6.1217(11)
_cell_length_b                   24.779(5)
_cell_length_c                   12.246(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.345(3)
_cell_angle_gamma                90.00
_cell_volume                     1838.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2718
_cell_measurement_theta_min      2.984
_cell_measurement_theta_max      25.782

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9470
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14883
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4404
_reflns_number_gt                3240
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0353P)²+1.8901P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4404
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O1 O 0.6809(3) 0.18777(8) 0.94229(13) 0.0307(4) Uani 1 1 d . . .
O2 O 0.1598(3) 0.08276(8) 0.95856(14) 0.0347(5) Uani 1 1 d . . .
N1 N 0.5800(3) 0.14744(8) 0.77758(17) 0.0221(4) Uani 1 1 d . . .
N2 N 0.4006(3) 0.12312(8) 0.81257(16) 0.0209(4) Uani 1 1 d . . .
N3 N 1.2737(3) 0.25181(8) 0.74449(17) 0.0225(4) Uani 1 1 d . . .
C1 C 1.2486(4) 0.25088(11) 0.8513(2) 0.0257(5) Uani 1 1 d . . .
C2 C 1.0694(4) 0.22591(10) 0.8841(2) 0.0236(5) Uani 1 1 d . . .
C3 C 0.9123(4) 0.20215(9) 0.80639(18) 0.0196(5) Uani 1 1 d . . .
C4 C 0.9424(4) 0.20354(10) 0.69579(19) 0.0224(5) Uani 1 1 d . . .
C5 C 1.1263(4) 0.22866(10) 0.6674(2) 0.0246(5) Uani 1 1 d . . .
C6 C 0.7150(4) 0.17847(10) 0.84853(18) 0.0208(5) Uani 1 1 d . . .
C7 C 0.2726(4) 0.09749(10) 0.73816(19) 0.0212(5) Uani 1 1 d . . .
C8 C 0.0784(4) 0.06927(9) 0.76213(19) 0.0205(5) Uani 1 1 d . . .
C9 C 0.0291(4) 0.06214(10) 0.86967(19) 0.0219(5) Uani 1 1 d . . .
C10 C -0.1550(4) 0.03285(10) 0.8870(2) 0.0262(6) Uani 1 1 d . . .
C11 C -0.2948(4) 0.01204(10) 0.7986(2) 0.0282(6) Uani 1 1 d . . .
C12 C -0.2532(5) 0.01996(11) 0.6917(2) 0.0290(6) Uani 1 1 d . . .
C13 C -0.0664(4) 0.04772(10) 0.6743(2) 0.0258(5) Uani 1 1 d . . .
S1 S 0.36331(11) 0.13131(3) 0.44052(5) 0.02361(17) Uani 1 1 d . . .
N4 N 0.1883(3) 0.17062(8) 0.36910(16) 0.0245(5) Uani 1 1 d . . .
O4 O 0.4941(3) 0.16085(7) 0.52914(13) 0.0296(4) Uani 1 1 d . . .
O5 O 0.2577(3) 0.08402(7) 0.47575(13) 0.0315(4) Uani 1 1 d . . .
O6 O 0.1151(3) 0.19995(7) 0.18985(13) 0.0254(4) Uani 1 1 d . . .
C15 C 0.5231(4) 0.11536(9) 0.33644(17) 0.0195(5) Uani 1 1 d . . .
C16 C 0.4232(4) 0.14130(9) 0.24189(18) 0.0190(5) Uani 1 1 d . . .
C17 C 0.5154(4) 0.13791(10) 0.14554(19) 0.0220(5) Uani 1 1 d . . .
C18 C 0.7068(4) 0.10824(10) 0.1469(2) 0.0256(5) Uani 1 1 d . . .
C19 C 0.8043(4) 0.08210(11) 0.2416(2) 0.0278(6) Uani 1 1 d . . .
C20 C 0.7127(4) 0.08539(11) 0.3388(2) 0.0266(6) Uani 1 1 d . . .
C21 C 0.2277(4) 0.17285(10) 0.26409(19) 0.0213(5) Uani 1 1 d . . .
H1 H 1.367(5) 0.2701(11) 0.898(2) 0.029(7) Uiso 1 1 d . . .
H2 H 1.044(4) 0.2248(10) 0.959(2) 0.026(7) Uiso 1 1 d . . .
H3 H 1.411(5) 0.2711(12) 0.724(2) 0.044(9) Uiso 1 1 d . . .
H4 H 0.835(4) 0.1883(10) 0.636(2) 0.022(7) Uiso 1 1 d . . .
H5 H 1.157(4) 0.2312(11) 0.595(2) 0.031(7) Uiso 1 1 d . . .
H7 H 0.302(4) 0.0944(11) 0.666(2) 0.029(7) Uiso 1 1 d . . .
H10 H -0.190(4) 0.0296(10) 0.961(2) 0.028(7) Uiso 1 1 d . . .
H11 H -0.419(5) -0.0082(11) 0.815(2) 0.027(7) Uiso 1 1 d . . .
H12 H -0.346(4) 0.0047(10) 0.632(2) 0.026(7) Uiso 1 1 d . . .
H13 H -0.034(4) 0.0527(11) 0.598(2) 0.028(7) Uiso 1 1 d . . .
H17 H 0.442(4) 0.1561(11) 0.083(2) 0.029(7) Uiso 1 1 d . . .
H18 H 0.772(5) 0.1074(11) 0.079(2) 0.034(8) Uiso 1 1 d . . .
H19 H 0.941(5) 0.0614(11) 0.241(2) 0.036(8) Uiso 1 1 d . . .
H20 H 0.775(5) 0.0666(11) 0.403(2) 0.031(7) Uiso 1 1 d . . .
H21 H 0.599(5) 0.1427(11) 0.714(2) 0.032(8) Uiso 1 1 d . . .
H22 H 0.279(7) 0.0994(17) 0.933(3) 0.089(14) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.219(3) . ?
O2 C9 1.354(3) . ?
O2 H22 0.93(4) . ?
N1 C6 1.349(3) . ?
N1 N2 1.375(3) . ?
N1 H21 0.82(3) . ?
N2 C7 1.281(3) . ?
N3 C5 1.337(3) . ?
N3 C1 1.339(3) . ?
N3 H3 1.03(3) . ?
C1 C2 1.370(3) . ?
C1 H1 0.98(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.95(3) . ?
C3 C4 1.394(3) . ?
C3 C6 1.500(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.98(3) . ?
C5 H5 0.93(3) . ?
C7 C8 1.446(3) . ?
C7 H7 0.93(3) . ?
C8 C13 1.397(3) . ?
C8 C9 1.404(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.379(4) . ?
C10 H10 0.96(3) . ?
C11 C12 1.383(4) . ?
C11 H11 0.95(3) . ?
C12 C13 1.377(4) . ?
C12 H12 0.94(3) . ?
C13 H13 0.99(3) . ?
S1 O5 1.4346(18) . ?
S1 O4 1.4501(18) . ?
S1 N4 1.609(2) . ?
S1 C15 1.760(2) . ?
N4 C21 1.344(3) . ?
O6 C21 1.253(3) . ?
C15 C20 1.375(3) . ?
C15 C16 1.386(3) . ?
C16 C17 1.382(3) . ?
C16 C21 1.487(3) . ?
C17 C18 1.381(4) . ?
C17 H17 0.94(3) . ?
C18 C19 1.386(4) . ?
C18 H18 0.97(3) . ?
C19 C20 1.389(4) . ?
C19 H19 0.98(3) . ?
C20 H20 0.95(3) . ?

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
C9 O2 H22 107(3) . . ?
C6 N1 N2 119.43(19) . . ?
C6 N1 H21 123(2) . . ?
N2 N1 H21 118(2) . . ?
C7 N2 N1 115.44(19) . . ?
C5 N3 C1 121.4(2) . . ?
C5 N3 H3 121.1(17) . . ?
C1 N3 H3 117.5(17) . . ?
N3 C1 C2 120.3(2) . . ?
N3 C1 H1 112.3(16) . . ?
C2 C1 H1 127.4(15) . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 122.9(16) . . ?
C3 C2 H2 117.3(16) . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 C6 116.3(2) . . ?
C4 C3 C6 124.8(2) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 118.2(15) . . ?
C3 C4 H4 122.7(15) . . ?
N3 C5 C4 120.6(2) . . ?
N3 C5 H5 115.4(17) . . ?
C4 C5 H5 123.9(17) . . ?
O1 C6 N1 122.8(2) . . ?
O1 C6 C3 120.5(2) . . ?
N1 C6 C3 116.7(2) . . ?
N2 C7 C8 122.1(2) . . ?
N2 C7 H7 122.1(17) . . ?
C8 C7 H7 115.7(17) . . ?
C13 C8 C9 118.4(2) . . ?
C13 C8 C7 118.5(2) . . ?
C9 C8 C7 123.1(2) . . ?
O2 C9 C10 118.3(2) . . ?
O2 C9 C8 121.6(2) . . ?
C10 C9 C8 120.1(2) . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 120.7(16) . . ?
C9 C10 H10 119.0(16) . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 117.1(16) . . ?
C12 C11 H11 122.2(16) . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.0(16) . . ?
C11 C12 H12 120.6(16) . . ?
C12 C13 C8 121.3(2) . . ?
C12 C13 H13 119.6(16) . . ?
C8 C13 H13 119.1(16) . . ?
O5 S1 O4 114.29(10) . . ?
O5 S1 N4 111.36(12) . . ?
O4 S1 N4 110.66(11) . . ?
O5 S1 C15 110.89(11) . . ?
O4 S1 C15 110.54(11) . . ?
N4 S1 C15 97.95(11) . . ?
C21 N4 S1 110.32(17) . . ?
C20 C15 C16 122.4(2) . . ?
C20 C15 S1 131.47(19) . . ?
C16 C15 S1 106.08(17) . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 C21 128.8(2) . . ?
C15 C16 C21 111.10(19) . . ?
C18 C17 C16 118.2(2) . . ?
C18 C17 H17 124.6(16) . . ?
C16 C17 H17 117.2(16) . . ?
C17 C18 C19 121.4(2) . . ?
C17 C18 H18 117.0(17) . . ?
C19 C18 H18 121.6(17) . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 H19 120.0(17) . . ?
C20 C19 H19 119.2(17) . . ?
C15 C20 C19 117.3(2) . . ?
C15 C20 H20 121.3(17) . . ?
C19 C20 H20 121.3(17) . . ?
O6 C21 N4 124.1(2) . . ?
O6 C21 C16 121.4(2) . . ?
N4 C21 C16 114.5(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H22 N2 0.93(4) 1.84(4) 2.671(3) 147(4) .
N1 H21 O4 0.82(3) 2.30(3) 3.030(3) 149(3) .
N3 H3 O6 1.03(3) 1.55(3) 2.579(3) 179(3) 4_766

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.061
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 1407125'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N3 O3, C7 H4 N O3 S'
_chemical_formula_sum            'C21 H18 N4 O6 S'
_chemical_formula_weight         454.45

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/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   6.1904(9)
_cell_length_b                   26.105(4)
_cell_length_c                   12.4015(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.464(2)
_cell_angle_gamma                90.00
_cell_volume                     1970.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2278
_cell_measurement_theta_min      5.875
_cell_measurement_theta_max      28.368

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9286
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16673
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4746
_reflns_number_gt                3159
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0500P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4746
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
O1 O 0.7414(3) 0.18941(6) 0.86397(12) 0.0360(4) Uani 1 1 d . . .
O2 O 0.2186(3) 0.08665(6) 0.86870(12) 0.0320(4) Uani 1 1 d . . .
O3 O -0.1178(3) 0.03070(6) 0.89476(12) 0.0340(4) Uani 1 1 d . . .
N1 N 0.6364(3) 0.15123(7) 0.69888(16) 0.0251(4) Uani 1 1 d . . .
N2 N 0.4576(3) 0.12779(6) 0.73074(14) 0.0240(4) Uani 1 1 d . . .
N3 N 1.3220(3) 0.25003(7) 0.67046(15) 0.0255(4) Uani 1 1 d . . .
C1 C 1.3017(4) 0.24969(8) 0.77606(18) 0.0272(5) Uani 1 1 d . . .
C2 C 1.1250(4) 0.22622(8) 0.80851(18) 0.0256(5) Uani 1 1 d . . .
C3 C 0.9654(3) 0.20361(7) 0.73053(16) 0.0219(4) Uani 1 1 d . . .
C4 C 0.9909(4) 0.20442(8) 0.62097(18) 0.0268(5) Uani 1 1 d . . .
C5 C 1.1714(4) 0.22813(8) 0.59326(19) 0.0270(5) Uani 1 1 d . . .
C6 C 0.7711(3) 0.18053(8) 0.77143(17) 0.0240(5) Uani 1 1 d . . .
C7 C 0.3277(4) 0.10477(8) 0.65371(18) 0.0261(5) Uani 1 1 d . . .
C8 C 0.1338(3) 0.07741(7) 0.67209(17) 0.0245(5) Uani 1 1 d . . .
C9 C 0.0882(3) 0.06873(7) 0.77665(16) 0.0221(4) Uani 1 1 d . . .
C10 C -0.0958(4) 0.03928(7) 0.78891(17) 0.0245(5) Uani 1 1 d . . .
C11 C -0.2355(4) 0.02138(8) 0.69765(19) 0.0305(5) Uani 1 1 d . . .
C12 C -0.1946(4) 0.03132(10) 0.5936(2) 0.0407(6) Uani 1 1 d . . .
C13 C -0.0120(4) 0.05867(10) 0.58032(19) 0.0387(6) Uani 1 1 d . . .
C14 C -0.3013(4) 0.00019(11) 0.9118(2) 0.0379(6) Uani 1 1 d . . .
S1 S 0.41072(9) 0.13825(2) 0.35908(4) 0.02558(15) Uani 1 1 d . . .
O4 O 0.5453(3) 0.16544(6) 0.44868(11) 0.0330(4) Uani 1 1 d . . .
O5 O 0.3050(3) 0.09318(6) 0.39140(12) 0.0365(4) Uani 1 1 d . . .
O6 O 0.1552(2) 0.20558(5) 0.11070(12) 0.0287(4) Uani 1 1 d . . .
N4 N 0.2354(3) 0.17639(7) 0.28786(14) 0.0264(4) Uani 1 1 d . . .
C15 C 0.5621(3) 0.12341(7) 0.25566(16) 0.0225(4) Uani 1 1 d . . .
C16 C 0.4617(3) 0.14874(7) 0.16243(15) 0.0209(4) Uani 1 1 d . . .
C17 C 0.5443(4) 0.14494(8) 0.06641(17) 0.0263(5) Uani 1 1 d . . .
C18 C 0.7299(4) 0.11490(9) 0.06717(19) 0.0325(5) Uani 1 1 d . . .
C19 C 0.8266(4) 0.08888(9) 0.1614(2) 0.0365(6) Uani 1 1 d . . .
C20 C 0.7455(4) 0.09270(9) 0.2579(2) 0.0320(5) Uani 1 1 d . . .
C21 C 0.2691(3) 0.17948(7) 0.18405(17) 0.0230(4) Uani 1 1 d . . .
H1 H 1.422(4) 0.2667(9) 0.8257(19) 0.038(7) Uiso 1 1 d . . .
H2 H 1.108(3) 0.2263(8) 0.8774(17) 0.021(5) Uiso 1 1 d . . .
H3 H 1.461(4) 0.2680(9) 0.645(2) 0.050(7) Uiso 1 1 d . . .
H4 H 0.891(3) 0.1901(7) 0.5675(16) 0.016(5) Uiso 1 1 d . . .
H5 H 1.194(4) 0.2303(8) 0.5186(18) 0.031(6) Uiso 1 1 d . . .
H7 H 0.357(4) 0.1049(9) 0.5833(19) 0.035(6) Uiso 1 1 d . . .
H11 H -0.363(4) 0.0006(8) 0.7066(18) 0.033(6) Uiso 1 1 d . . .
H12 H -0.288(4) 0.0187(9) 0.534(2) 0.044(7) Uiso 1 1 d . . .
H13 H 0.021(4) 0.0638(9) 0.509(2) 0.040(7) Uiso 1 1 d . . .
H14A H -0.296(4) -0.0351(10) 0.8802(19) 0.042(7) Uiso 1 1 d . . .
H14B H -0.283(4) -0.0040(9) 0.990(2) 0.041(7) Uiso 1 1 d . . .
H14C H -0.440(4) 0.0175(9) 0.8850(18) 0.036(7) Uiso 1 1 d . . .
H17 H 0.479(3) 0.1626(8) 0.0039(17) 0.023(6) Uiso 1 1 d . . .
H18 H 0.785(4) 0.1113(9) 0.002(2) 0.041(7) Uiso 1 1 d . . .
H19 H 0.955(5) 0.0668(10) 0.159(2) 0.056(8) Uiso 1 1 d . . .
H20 H 0.811(4) 0.0751(9) 0.3225(19) 0.037(7) Uiso 1 1 d . . .
H21 H 0.645(4) 0.1493(9) 0.631(2) 0.037(7) Uiso 1 1 d . . .
H22 H 0.327(5) 0.1031(11) 0.844(2) 0.063(9) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.217(2) . ?
O2 C9 1.356(2) . ?
O2 H22 0.90(3) . ?
O3 C10 1.363(2) . ?
O3 C14 1.434(3) . ?
N1 C6 1.348(3) . ?
N1 N2 1.383(2) . ?
N1 H21 0.86(2) . ?
N2 C7 1.281(3) . ?
N3 C5 1.337(3) . ?
N3 C1 1.338(3) . ?
N3 H3 1.08(3) . ?
C1 C2 1.376(3) . ?
C1 H1 0.98(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.88(2) . ?
C3 C4 1.396(3) . ?
C3 C6 1.513(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.90(2) . ?
C5 H5 0.96(2) . ?
C7 C8 1.450(3) . ?
C7 H7 0.92(2) . ?
C8 C9 1.395(3) . ?
C8 C13 1.406(3) . ?
C9 C10 1.405(3) . ?
C10 C11 1.376(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.98(2) . ?
C12 C13 1.372(3) . ?
C12 H12 0.91(2) . ?
C13 H13 0.95(2) . ?
C14 H14A 1.00(2) . ?
C14 H14B 0.96(2) . ?
C14 H14C 0.98(2) . ?
S1 O5 1.4383(15) . ?
S1 O4 1.4479(15) . ?
S1 N4 1.6129(18) . ?
S1 C15 1.764(2) . ?
O6 C21 1.247(2) . ?
N4 C21 1.344(3) . ?
C15 C16 1.378(3) . ?
C15 C20 1.386(3) . ?
C16 C17 1.382(3) . ?
C16 C21 1.501(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.93(2) . ?
C18 C19 1.390(3) . ?
C18 H18 0.93(2) . ?
C19 C20 1.382(3) . ?
C19 H19 0.99(3) . ?
C20 H20 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H22 104.3(18) . . ?
C10 O3 C14 117.00(19) . . ?
C6 N1 N2 119.36(18) . . ?
C6 N1 H21 123.3(16) . . ?
N2 N1 H21 116.8(16) . . ?
C7 N2 N1 114.88(17) . . ?
C5 N3 C1 121.37(19) . . ?
C5 N3 H3 118.1(13) . . ?
C1 N3 H3 120.6(13) . . ?
N3 C1 C2 120.7(2) . . ?
N3 C1 H1 114.4(14) . . ?
C2 C1 H1 124.9(14) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 121.8(14) . . ?
C3 C2 H2 118.8(14) . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 C6 116.47(18) . . ?
C4 C3 C6 124.72(19) . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 118.9(13) . . ?
C3 C4 H4 121.7(13) . . ?
N3 C5 C4 120.4(2) . . ?
N3 C5 H5 117.5(13) . . ?
C4 C5 H5 122.1(13) . . ?
O1 C6 N1 123.8(2) . . ?
O1 C6 C3 120.39(19) . . ?
N1 C6 C3 115.81(18) . . ?
N2 C7 C8 122.6(2) . . ?
N2 C7 H7 119.9(15) . . ?
C8 C7 H7 117.5(15) . . ?
C9 C8 C13 119.2(2) . . ?
C9 C8 C7 122.64(19) . . ?
C13 C8 C7 118.18(19) . . ?
O2 C9 C8 122.44(18) . . ?
O2 C9 C10 117.91(18) . . ?
C8 C9 C10 119.63(19) . . ?
O3 C10 C11 125.4(2) . . ?
O3 C10 C9 114.78(19) . . ?
C11 C10 C9 119.86(19) . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.6(13) . . ?
C12 C11 H11 119.8(13) . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 120.6(15) . . ?
C11 C12 H12 119.1(16) . . ?
C12 C13 C8 120.4(2) . . ?
C12 C13 H13 120.2(14) . . ?
C8 C13 H13 119.3(14) . . ?
O3 C14 H14A 111.6(14) . . ?
O3 C14 H14B 105.3(15) . . ?
H14A C14 H14B 106.5(19) . . ?
O3 C14 H14C 111.4(14) . . ?
H14A C14 H14C 112.4(19) . . ?
H14B C14 H14C 109.3(19) . . ?
O5 S1 O4 114.50(9) . . ?
O5 S1 N4 111.26(10) . . ?
O4 S1 N4 110.72(9) . . ?
O5 S1 C15 110.60(9) . . ?
O4 S1 C15 110.98(10) . . ?
N4 S1 C15 97.54(9) . . ?
C21 N4 S1 110.83(14) . . ?
C16 C15 C20 122.52(19) . . ?
C16 C15 S1 106.63(15) . . ?
C20 C15 S1 130.85(17) . . ?
C15 C16 C17 120.46(19) . . ?
C15 C16 C21 111.02(17) . . ?
C17 C16 C21 128.49(19) . . ?
C16 C17 C18 118.0(2) . . ?
C16 C17 H17 120.6(13) . . ?
C18 C17 H17 121.4(13) . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 H18 118.7(15) . . ?
C19 C18 H18 120.5(15) . . ?
C20 C19 C18 121.6(2) . . ?
C20 C19 H19 119.6(16) . . ?
C18 C19 H19 118.8(16) . . ?
C19 C20 C15 116.7(2) . . ?
C19 C20 H20 122.0(15) . . ?
C15 C20 H20 121.3(15) . . ?
O6 C21 N4 124.47(19) . . ?
O6 C21 C16 121.59(18) . . ?
N4 C21 C16 113.93(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H22 N2 0.90(3) 1.86(3) 2.681(2) 152(3) .
N1 H21 O4 0.86(2) 2.27(2) 3.074(2) 156(2) .
N3 H3 O6 1.08(3) 1.51(3) 2.589(2) 179(2) 4_766

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.054
