# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kck4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N4 O2 S'
_chemical_formula_weight         326.37

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.1492(7)
_cell_length_b                   7.7691(8)
_cell_length_c                   14.105(2)
_cell_angle_alpha                97.012(10)
_cell_angle_beta                 102.997(10)
_cell_angle_gamma                98.628(8)
_cell_volume                     744.79(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2464
_cell_measurement_theta_min      3.2950
_cell_measurement_theta_max      28.9360

_exptl_crystal_description       needles
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5120
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3024
_reflns_number_gt                2531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0635P)²+0.1516P] 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         3024
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.06288(7) 0.16665(5) 0.19946(3) 0.03976(16) Uani 1 1 d . . .
N1 N 0.2467(2) 0.51417(17) 0.30957(10) 0.0335(3) Uani 1 1 d . . .
N2 N 0.2717(2) 0.66852(18) 0.37088(11) 0.0374(3) Uani 1 1 d . . .
N3 N 0.2718(2) 0.62955(18) 0.45800(11) 0.0371(3) Uani 1 1 d . . .
O1 O 0.0843(2) 0.00271(16) 0.14984(10) 0.0548(4) Uani 1 1 d . . .
C7 C 0.2287(2) 0.3755(2) 0.35996(12) 0.0329(4) Uani 1 1 d . . .
O2 O -0.1249(2) 0.19328(18) 0.20867(10) 0.0501(4) Uani 1 1 d . . .
C8 C 0.2433(2) 0.4495(2) 0.45484(12) 0.0332(4) Uani 1 1 d . . .
C2 C 0.1678(3) 0.3230(3) 0.04928(14) 0.0440(4) Uani 1 1 d . . .
H9 H 0.1213 0.2142 0.0086 0.053 Uiso 1 1 calc R . .
C5 C 0.3127(3) 0.6475(2) 0.17015(13) 0.0371(4) Uani 1 1 d . . .
H10 H 0.3617 0.7558 0.2111 0.044 Uiso 1 1 calc R . .
C9 C 0.2305(2) 0.3715(2) 0.54357(13) 0.0356(4) Uani 1 1 d . . .
C6 C 0.2406(3) 0.5034(2) 0.20833(12) 0.0335(4) Uani 1 1 d . . .
C4 C 0.3122(3) 0.6316(3) 0.07145(14) 0.0410(4) Uani 1 1 d . . .
C14 C 0.2335(3) 0.4805(3) 0.62978(14) 0.0429(4) Uani 1 1 d . . .
H14 H 0.2445 0.6015 0.6310 0.051 Uiso 1 1 calc R . .
C1 C 0.1649(3) 0.3411(2) 0.14769(13) 0.0366(4) Uani 1 1 d . . .
C11 C 0.1965(3) 0.1217(3) 0.62798(16) 0.0523(5) Uani 1 1 d . . .
H17 H 0.1826 0.0006 0.6273 0.063 Uiso 1 1 calc R . .
C3 C 0.2404(3) 0.4679(3) 0.01214(14) 0.0473(5) Uani 1 1 d . . .
H18 H 0.2413 0.4558 -0.0542 0.057 Uiso 1 1 calc R . .
C15 C 0.3892(3) 0.7910(3) 0.03092(16) 0.0551(6) Uani 1 1 d . . .
H19A H 0.3016 0.8734 0.0304 0.083 Uiso 1 1 calc R . .
H19B H 0.3992 0.7552 -0.0351 0.083 Uiso 1 1 calc R . .
H19C H 0.5158 0.8458 0.0717 0.083 Uiso 1 1 calc R . .
C10 C 0.2117(3) 0.1903(2) 0.54338(15) 0.0455(5) Uani 1 1 d . . .
H20 H 0.2094 0.1153 0.4863 0.055 Uiso 1 1 calc R . .
C13 C 0.2202(3) 0.4101(3) 0.71362(16) 0.0530(5) Uani 1 1 d . . .
H21 H 0.2238 0.4843 0.7712 0.064 Uiso 1 1 calc R . .
C12 C 0.2018(3) 0.2316(3) 0.71297(16) 0.0551(6) Uani 1 1 d . . .
H22 H 0.1930 0.1852 0.7699 0.066 Uiso 1 1 calc R . .
N4 N 0.2066(2) 0.20114(18) 0.31176(11) 0.0369(4) Uani 1 1 d . . .
C16 C 0.3819(3) 0.1174(3) 0.32835(16) 0.0526(5) Uani 1 1 d . . .
H1A H 0.3424 -0.0078 0.3230 0.079 Uiso 1 1 calc R . .
H1B H 0.4638 0.1641 0.3930 0.079 Uiso 1 1 calc R . .
H1C H 0.4529 0.1416 0.2798 0.079 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0492(3) 0.0305(2) 0.0328(3) -0.00078(18) 0.0055(2) -0.00198(19)
N1 0.0431(8) 0.0252(7) 0.0295(7) 0.0022(5) 0.0073(6) 0.0029(6)
N2 0.0480(9) 0.0277(7) 0.0329(8) 0.0003(6) 0.0075(7) 0.0035(6)
N3 0.0455(9) 0.0314(7) 0.0320(8) 0.0018(6) 0.0082(6) 0.0038(6)
O1 0.0811(11) 0.0325(7) 0.0428(8) -0.0053(6) 0.0112(7) 0.0008(7)
C7 0.0376(9) 0.0271(8) 0.0323(9) 0.0050(7) 0.0062(7) 0.0041(7)
O2 0.0436(8) 0.0530(8) 0.0474(8) 0.0075(6) 0.0062(6) -0.0034(6)
C8 0.0345(9) 0.0310(8) 0.0311(9) 0.0018(7) 0.0055(7) 0.0031(7)
C2 0.0510(11) 0.0442(10) 0.0329(10) -0.0025(8) 0.0078(8) 0.0075(9)
C5 0.0409(10) 0.0329(9) 0.0369(10) 0.0062(7) 0.0087(8) 0.0063(7)
C9 0.0316(9) 0.0400(9) 0.0318(9) 0.0065(7) 0.0045(7) 0.0011(7)
C6 0.0372(9) 0.0327(8) 0.0299(9) 0.0047(7) 0.0068(7) 0.0070(7)
C4 0.0395(10) 0.0487(11) 0.0401(10) 0.0161(8) 0.0128(8) 0.0130(8)
C14 0.0465(11) 0.0454(10) 0.0355(10) 0.0045(8) 0.0114(8) 0.0046(8)
C1 0.0418(10) 0.0332(9) 0.0325(9) 0.0025(7) 0.0070(8) 0.0051(7)
C11 0.0523(12) 0.0490(11) 0.0537(13) 0.0223(10) 0.0078(10) 0.0004(9)
C3 0.0538(12) 0.0591(12) 0.0315(10) 0.0088(9) 0.0135(9) 0.0127(10)
C15 0.0616(14) 0.0581(13) 0.0542(13) 0.0244(11) 0.0227(11) 0.0120(10)
C10 0.0515(12) 0.0412(10) 0.0404(11) 0.0071(8) 0.0084(9) 0.0024(8)
C13 0.0567(13) 0.0666(14) 0.0363(11) 0.0091(10) 0.0149(9) 0.0073(10)
C12 0.0510(12) 0.0725(15) 0.0414(12) 0.0242(11) 0.0094(9) 0.0011(10)
N4 0.0476(9) 0.0265(7) 0.0325(8) 0.0010(6) 0.0054(7) 0.0045(6)
C16 0.0612(13) 0.0372(10) 0.0541(13) -0.0013(9) 0.0039(10) 0.0154(9)

_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 1.4201(15) . ?
S1 O1 1.4229(13) . ?
S1 N4 1.6487(15) . ?
S1 C1 1.7569(18) . ?
N1 N2 1.3530(18) . ?
N1 C7 1.367(2) . ?
N1 C6 1.411(2) . ?
N2 N3 1.301(2) . ?
N3 C8 1.377(2) . ?
C7 C8 1.365(2) . ?
C7 N4 1.408(2) . ?
C8 C9 1.471(2) . ?
C2 C3 1.379(3) . ?
C2 C1 1.383(3) . ?
C2 H9 0.9300 . ?
C5 C6 1.381(2) . ?
C5 C4 1.382(3) . ?
C5 H10 0.9300 . ?
C9 C14 1.388(2) . ?
C9 C10 1.393(3) . ?
C6 C1 1.392(2) . ?
C4 C3 1.390(3) . ?
C4 C15 1.508(3) . ?
C14 C13 1.378(3) . ?
C14 H14 0.9300 . ?
C11 C12 1.374(3) . ?
C11 C10 1.384(3) . ?
C11 H17 0.9300 . ?
C3 H18 0.9300 . ?
C15 H19A 0.9600 . ?
C15 H19B 0.9600 . ?
C15 H19C 0.9600 . ?
C10 H20 0.9300 . ?
C13 C12 1.371(3) . ?
C13 H21 0.9300 . ?
C12 H22 0.9300 . ?
N4 C16 1.483(2) . ?
C16 H1A 0.9600 . ?
C16 H1B 0.9600 . ?
C16 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.63(9) . . ?
O2 S1 N4 107.18(8) . . ?
O1 S1 N4 108.03(8) . . ?
O2 S1 C1 108.42(8) . . ?
O1 S1 C1 109.95(9) . . ?
N4 S1 C1 102.19(8) . . ?
N2 N1 C7 110.32(13) . . ?
N2 N1 C6 123.34(13) . . ?
C7 N1 C6 126.34(14) . . ?
N3 N2 N1 106.85(13) . . ?
N2 N3 C8 110.39(14) . . ?
C8 C7 N1 105.33(14) . . ?
C8 C7 N4 134.10(15) . . ?
N1 C7 N4 120.54(15) . . ?
C7 C8 N3 107.09(14) . . ?
C7 C8 C9 131.98(15) . . ?
N3 C8 C9 120.92(15) . . ?
C3 C2 C1 119.28(18) . . ?
C3 C2 H9 120.4 . . ?
C1 C2 H9 120.4 . . ?
C6 C5 C4 120.27(17) . . ?
C6 C5 H10 119.9 . . ?
C4 C5 H10 119.9 . . ?
C14 C9 C10 118.75(17) . . ?
C14 C9 C8 119.32(16) . . ?
C10 C9 C8 121.92(16) . . ?
C5 C6 C1 120.44(16) . . ?
C5 C6 N1 121.46(15) . . ?
C1 C6 N1 118.08(15) . . ?
C5 C4 C3 118.76(17) . . ?
C5 C4 C15 119.47(18) . . ?
C3 C4 C15 121.77(18) . . ?
C13 C14 C9 120.32(19) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C2 C1 C6 119.65(17) . . ?
C2 C1 S1 122.27(14) . . ?
C6 C1 S1 118.06(13) . . ?
C12 C11 C10 120.35(19) . . ?
C12 C11 H17 119.8 . . ?
C10 C11 H17 119.8 . . ?
C2 C3 C4 121.56(18) . . ?
C2 C3 H18 119.2 . . ?
C4 C3 H18 119.2 . . ?
C4 C15 H19A 109.5 . . ?
C4 C15 H19B 109.5 . . ?
H19A C15 H19B 109.5 . . ?
C4 C15 H19C 109.5 . . ?
H19A C15 H19C 109.5 . . ?
H19B C15 H19C 109.5 . . ?
C11 C10 C9 120.15(19) . . ?
C11 C10 H20 119.9 . . ?
C9 C10 H20 119.9 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H21 119.7 . . ?
C14 C13 H21 119.7 . . ?
C13 C12 C11 119.77(19) . . ?
C13 C12 H22 120.1 . . ?
C11 C12 H22 120.1 . . ?
C7 N4 C16 116.99(14) . . ?
C7 N4 S1 112.53(11) . . ?
C16 N4 S1 118.09(12) . . ?
N4 C16 H1A 109.5 . . ?
N4 C16 H1B 109.5 . . ?
H1A C16 H1B 109.5 . . ?
N4 C16 H1C 109.5 . . ?
H1A C16 H1C 109.5 . . ?
H1B C16 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 992617'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kck14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N4 O2 S'
_chemical_formula_weight         250.28

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

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                   8.0936(11)
_cell_length_b                   21.469(3)
_cell_length_c                   6.2322(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.001(11)
_cell_angle_gamma                90.00
_cell_volume                     1078.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1481
_cell_measurement_theta_min      3.8030
_cell_measurement_theta_max      28.2600

_exptl_crystal_description       needles
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4271
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2203
_reflns_number_gt                1848
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.3483P] 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         2203
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.34840(6) 0.63710(3) 0.93127(9) 0.0395(2) Uani 1 1 d . . .
C1 C 0.0144(2) 0.62848(9) 0.8238(3) 0.0288(4) Uani 1 1 d . . .
N1 N 0.0124(2) 0.59291(8) 1.0123(3) 0.0317(4) Uani 1 1 d . . .
N2 N -0.1306(2) 0.57633(9) 1.0989(3) 0.0398(5) Uani 1 1 d . . .
C5 C 0.1754(3) 0.67974(10) 0.5719(3) 0.0357(5) Uani 1 1 d . . .
H5 H 0.2773 0.6914 0.5264 0.043 Uiso 1 1 calc R . .
C6 C 0.1677(3) 0.64679(10) 0.7613(3) 0.0309(5) Uani 1 1 d . . .
C2 C -0.1298(3) 0.64386(10) 0.7023(3) 0.0339(5) Uani 1 1 d . . .
H2 H -0.2316 0.6313 0.7459 0.041 Uiso 1 1 calc R . .
N4 N 0.3040(2) 0.57326(9) 1.0617(3) 0.0379(4) Uani 1 1 d . . .
C3 C -0.1232(3) 0.67809(10) 0.5153(3) 0.0349(5) Uani 1 1 d . . .
C7 C 0.1453(3) 0.56760(10) 1.1255(3) 0.0330(5) Uani 1 1 d . . .
C4 C 0.0311(3) 0.69509(10) 0.4518(3) 0.0383(5) Uani 1 1 d . . .
H4 H 0.0366 0.7174 0.3247 0.046 Uiso 1 1 calc R . .
O1 O 0.4837(2) 0.62253(11) 0.8099(3) 0.0687(6) Uani 1 1 d . . .
N3 N -0.0860(3) 0.54184(10) 1.2646(3) 0.0454(5) Uani 1 1 d . . .
O2 O 0.3651(2) 0.68793(8) 1.0782(3) 0.0632(5) Uani 1 1 d . . .
C8 C 0.0814(3) 0.53540(11) 1.2867(3) 0.0424(6) Uani 1 1 d . . .
H8 H 0.1420 0.5128 1.3938 0.051 Uiso 1 1 calc R . .
C9 C -0.2807(3) 0.69621(13) 0.3843(4) 0.0502(6) Uani 1 1 d . . .
H9A H -0.3724 0.6742 0.4362 0.075 Uiso 1 1 calc R . .
H9B H -0.2721 0.6858 0.2359 0.075 Uiso 1 1 calc R . .
H9C H -0.2981 0.7402 0.3971 0.075 Uiso 1 1 calc R . .
C10 C 0.4388(3) 0.54766(13) 1.2086(4) 0.0540(7) Uani 1 1 d . . .
H10A H 0.4377 0.5671 1.3472 0.081 Uiso 1 1 calc R . .
H10B H 0.5432 0.5556 1.1516 0.081 Uiso 1 1 calc R . .
H10C H 0.4236 0.5036 1.2230 0.081 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0257(3) 0.0409(4) 0.0509(4) 0.0123(3) -0.0011(2) -0.0018(2)
C1 0.0294(10) 0.0289(10) 0.0286(9) 0.0009(8) 0.0044(8) -0.0021(8)
N1 0.0304(9) 0.0349(10) 0.0302(8) 0.0056(7) 0.0055(7) -0.0025(8)
N2 0.0366(10) 0.0474(12) 0.0368(10) 0.0061(9) 0.0112(8) -0.0051(9)
C5 0.0335(11) 0.0365(12) 0.0381(11) 0.0038(9) 0.0083(9) -0.0033(9)
C6 0.0279(10) 0.0314(11) 0.0335(10) 0.0021(9) 0.0026(8) 0.0008(9)
C2 0.0281(11) 0.0376(12) 0.0359(11) 0.0000(9) 0.0016(8) -0.0036(9)
N4 0.0324(10) 0.0389(11) 0.0417(10) 0.0103(8) 0.0001(8) 0.0039(8)
C3 0.0371(12) 0.0336(11) 0.0329(10) -0.0008(9) -0.0031(9) 0.0003(9)
C7 0.0350(11) 0.0307(11) 0.0332(10) 0.0021(9) 0.0036(8) 0.0008(9)
C4 0.0467(13) 0.0374(12) 0.0306(10) 0.0079(9) 0.0021(9) -0.0025(10)
O1 0.0314(9) 0.0938(16) 0.0836(13) 0.0388(12) 0.0202(9) 0.0137(10)
N3 0.0514(12) 0.0480(12) 0.0385(10) 0.0094(9) 0.0141(9) -0.0051(10)
O2 0.0643(12) 0.0418(10) 0.0769(12) 0.0013(9) -0.0311(10) -0.0094(9)
C8 0.0518(14) 0.0404(13) 0.0351(11) 0.0077(10) 0.0048(10) 0.0006(11)
C9 0.0431(14) 0.0558(16) 0.0492(13) 0.0078(12) -0.0109(11) 0.0026(12)
C10 0.0446(14) 0.0574(17) 0.0581(15) 0.0154(13) -0.0054(11) 0.0139(13)

_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 O1 1.4188(18) . ?
S1 O2 1.4233(19) . ?
S1 N4 1.6491(18) . ?
S1 C6 1.742(2) . ?
C1 C2 1.374(3) . ?
C1 C6 1.389(3) . ?
C1 N1 1.403(2) . ?
N1 C7 1.348(3) . ?
N1 N2 1.366(2) . ?
N2 N3 1.296(3) . ?
C5 C4 1.371(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
N4 C7 1.383(3) . ?
N4 C10 1.468(3) . ?
C3 C4 1.392(3) . ?
C3 C9 1.504(3) . ?
C7 C8 1.358(3) . ?
C4 H4 0.9300 . ?
N3 C8 1.357(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
O1 S1 O2 118.51(13) . . ?
O1 S1 N4 106.91(11) . . ?
O2 S1 N4 109.43(11) . . ?
O1 S1 C6 110.38(11) . . ?
O2 S1 C6 109.11(11) . . ?
N4 S1 C6 101.05(10) . . ?
C2 C1 C6 120.91(18) . . ?
C2 C1 N1 121.39(18) . . ?
C6 C1 N1 117.69(18) . . ?
C7 N1 N2 110.67(16) . . ?
C7 N1 C1 126.23(17) . . ?
N2 N1 C1 123.01(17) . . ?
N3 N2 N1 106.09(17) . . ?
C4 C5 C6 119.34(19) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.46(19) . . ?
C5 C6 S1 118.87(16) . . ?
C1 C6 S1 121.25(15) . . ?
C1 C2 C3 119.91(19) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C7 N4 C10 116.49(18) . . ?
C7 N4 S1 117.56(15) . . ?
C10 N4 S1 115.88(16) . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 C9 120.1(2) . . ?
C4 C3 C9 121.1(2) . . ?
N1 C7 C8 104.74(19) . . ?
N1 C7 N4 122.19(18) . . ?
C8 C7 N4 132.9(2) . . ?
C5 C4 C3 121.61(19) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
N2 N3 C8 110.18(18) . . ?
N3 C8 C7 108.3(2) . . ?
N3 C8 H8 125.8 . . ?
C7 C8 H8 125.8 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 992618'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kck21

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O5 S'
_chemical_formula_weight         374.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   10.3978(17)
_cell_length_b                   19.453(4)
_cell_length_c                   9.6211(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.179(16)
_cell_angle_gamma                90.00
_cell_volume                     1930.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1680
_cell_measurement_theta_min      4.2990
_cell_measurement_theta_max      70.3480


_exptl_crystal_description       needles
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    1.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6419
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         71.49
_reflns_number_total             3614
_reflns_number_gt                2152
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1607P)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         3614
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.2664
_refine_ls_wR_factor_gt          0.1826
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.014
_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
C9 C 0.8336(4) 0.1324(2) -0.0198(4) 0.0370(9) Uani 1 1 d . . .
C10 C 0.9375(4) 0.1069(2) 0.0685(5) 0.0445(11) Uani 1 1 d . . .
H10 H 1.0139 0.1322 0.0847 0.053 Uiso 1 1 calc R . .
C6 C 1.0492(4) 0.3262(2) -0.0599(5) 0.0395(10) Uani 1 1 d . . .
C11 C 0.9282(5) 0.0433(3) 0.1337(5) 0.0516(12) Uani 1 1 d . . .
C14 C 0.7190(4) 0.0955(2) -0.0435(5) 0.0438(10) Uani 1 1 d . . .
C13 C 0.7104(5) 0.0318(3) 0.0194(7) 0.0602(14) Uani 1 1 d . . .
H13 H 0.6350 0.0059 0.0006 0.072 Uiso 1 1 calc R . .
C1 C 1.1097(5) 0.3589(3) 0.0576(6) 0.0586(14) Uani 1 1 d . . .
H1 H 1.0606 0.3774 0.1228 0.070 Uiso 1 1 calc R . .
C17 C 1.0412(6) 0.0165(3) 0.2341(6) 0.0682(16) Uani 1 1 d . . .
H17A H 1.1169 0.0437 0.2256 0.102 Uiso 1 1 calc R . .
H17B H 1.0579 -0.0305 0.2119 0.102 Uiso 1 1 calc R . .
H17C H 1.0204 0.0193 0.3284 0.102 Uiso 1 1 calc R . .
C12 C 0.8139(5) 0.0065(3) 0.1103(7) 0.0656(15) Uani 1 1 d . . .
H12 H 0.8062 -0.0353 0.1556 0.079 Uiso 1 1 calc R . .
C5 C 1.1234(4) 0.2964(3) -0.1540(6) 0.0568(13) Uani 1 1 d . . .
H5 H 1.0836 0.2731 -0.2322 0.068 Uiso 1 1 calc R . .
C4 C 1.2581(5) 0.3017(4) -0.1307(8) 0.081(2) Uani 1 1 d . . .
H4 H 1.3084 0.2819 -0.1934 0.097 Uiso 1 1 calc R . .
C3 C 1.3168(5) 0.3364(3) -0.0139(8) 0.0770(19) Uani 1 1 d . . .
H3 H 1.4066 0.3406 0.0008 0.092 Uiso 1 1 calc R . .
C2 C 1.2440(5) 0.3640(3) 0.0784(7) 0.0721(18) Uani 1 1 d . . .
H2 H 1.2842 0.3868 0.1571 0.087 Uiso 1 1 calc R . .
C7 C 0.9033(4) 0.3192(2) -0.0866(4) 0.0358(9) Uani 1 1 d . . .
H7 H 0.8753 0.3131 -0.1869 0.043 Uiso 1 1 calc R . .
C8 C 0.8660(3) 0.2564(2) -0.0051(4) 0.0345(9) Uani 1 1 d . . .
O3 O 0.8601(3) 0.25862(16) 0.1211(3) 0.0478(8) Uani 1 1 d . . .
O4 O 0.8461(3) 0.37998(15) -0.0363(3) 0.0428(7) Uani 1 1 d . . .
O5 O 0.6515(3) 0.3355(2) -0.1106(4) 0.0596(10) Uani 1 1 d . . .
C15 C 0.7149(4) 0.3826(3) -0.0621(5) 0.0473(11) Uani 1 1 d . . .
C16 C 0.6635(5) 0.4516(3) -0.0281(8) 0.0727(17) Uani 1 1 d . . .
H16A H 0.6276 0.4740 -0.1131 0.109 Uiso 1 1 calc R . .
H16B H 0.7327 0.4790 0.0184 0.109 Uiso 1 1 calc R . .
H16C H 0.5973 0.4460 0.0321 0.109 Uiso 1 1 calc R . .
S1 S 0.58209(10) 0.12841(7) -0.15179(13) 0.0505(4) Uani 1 1 d . . .
O1 O 0.4849(3) 0.0768(2) -0.1600(4) 0.0720(12) Uani 1 1 d . . .
N2 N 0.8469(3) 0.19831(18) -0.0810(3) 0.0355(8) Uani 1 1 d . . .
H2A H 0.8426 0.2011 -0.1706 0.043 Uiso 1 1 calc R . .
O2 O 0.6237(3) 0.1546(2) -0.2777(4) 0.0651(11) Uani 1 1 d . . .
N1 N 0.5323(4) 0.1937(2) -0.0696(5) 0.0565(11) Uani 1 1 d . . .
H1A H 0.5318 0.2343 -0.1050 0.068 Uiso 1 1 calc R . .
C18 C 0.4879(7) 0.1815(4) 0.0673(7) 0.087(2) Uani 1 1 d . . .
H18A H 0.4318 0.1421 0.0615 0.131 Uiso 1 1 calc R . .
H18B H 0.4415 0.2211 0.0938 0.131 Uiso 1 1 calc R . .
H18C H 0.5614 0.1733 0.1361 0.131 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C9 0.041(2) 0.034(2) 0.037(2) 0.0014(18) 0.0084(16) -0.0012(16)
C10 0.044(2) 0.040(2) 0.049(3) 0.000(2) 0.0043(19) 0.0023(18)
C6 0.0350(19) 0.037(2) 0.047(3) 0.0010(19) 0.0059(17) -0.0027(16)
C11 0.061(3) 0.040(3) 0.053(3) -0.015(2) 0.007(2) 0.011(2)
C14 0.0392(19) 0.040(2) 0.052(3) 0.002(2) 0.0063(18) -0.0003(18)
C13 0.053(3) 0.046(3) 0.083(4) 0.010(3) 0.011(3) -0.007(2)
C1 0.050(2) 0.054(3) 0.071(4) -0.018(3) 0.001(2) -0.001(2)
C17 0.078(4) 0.057(3) 0.068(4) 0.005(3) 0.005(3) 0.025(3)
C12 0.068(3) 0.043(3) 0.088(4) 0.021(3) 0.019(3) -0.001(2)
C5 0.045(2) 0.071(4) 0.055(3) -0.002(3) 0.010(2) 0.008(2)
C4 0.047(3) 0.102(5) 0.098(5) 0.007(4) 0.024(3) 0.021(3)
C3 0.035(2) 0.075(4) 0.119(6) 0.019(4) 0.002(3) 0.000(2)
C2 0.046(3) 0.064(4) 0.101(5) 0.004(3) -0.013(3) -0.007(3)
C7 0.0356(18) 0.037(2) 0.035(2) 0.0050(18) 0.0024(16) 0.0005(16)
C8 0.0316(17) 0.035(2) 0.037(2) -0.0045(18) 0.0038(15) 0.0026(15)
O3 0.0689(19) 0.0446(18) 0.0312(17) 0.0017(14) 0.0112(14) 0.0010(15)
O4 0.0410(14) 0.0364(16) 0.0512(19) -0.0015(14) 0.0068(13) 0.0031(12)
O5 0.0401(16) 0.068(2) 0.069(2) -0.006(2) 0.0002(16) 0.0030(16)
C15 0.045(2) 0.049(3) 0.047(3) 0.005(2) 0.006(2) 0.007(2)
C16 0.062(3) 0.054(3) 0.106(5) -0.003(3) 0.023(3) 0.018(3)
S1 0.0399(6) 0.0576(8) 0.0525(8) 0.0031(6) 0.0006(5) -0.0070(5)
O1 0.0517(19) 0.074(3) 0.086(3) 0.015(2) -0.0091(18) -0.0224(18)
N2 0.0433(17) 0.0367(19) 0.0275(18) -0.0037(15) 0.0080(14) -0.0034(14)
O2 0.0571(19) 0.091(3) 0.047(2) -0.004(2) 0.0042(16) -0.0097(19)
N1 0.050(2) 0.060(3) 0.059(3) 0.013(2) 0.0032(18) 0.0113(19)
C18 0.102(5) 0.099(5) 0.065(4) 0.010(4) 0.030(4) 0.029(4)

_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
C9 C14 1.385(6) . ?
C9 C10 1.381(6) . ?
C9 N2 1.425(5) . ?
C10 C11 1.395(7) . ?
C6 C1 1.378(7) . ?
C6 C5 1.388(6) . ?
C6 C7 1.512(5) . ?
C11 C12 1.383(7) . ?
C11 C17 1.518(7) . ?
C14 C13 1.387(7) . ?
C14 S1 1.775(4) . ?
C13 C12 1.389(8) . ?
C1 C2 1.390(7) . ?
C5 C4 1.394(7) . ?
C4 C3 1.386(10) . ?
C3 C2 1.349(9) . ?
C7 O4 1.435(5) . ?
C7 C8 1.528(6) . ?
C8 O3 1.224(5) . ?
C8 N2 1.346(5) . ?
O4 C15 1.356(5) . ?
O5 C15 1.190(6) . ?
C15 C16 1.495(7) . ?
S1 O1 1.420(4) . ?
S1 O2 1.430(4) . ?
S1 N1 1.615(5) . ?
N1 C18 1.469(7) . ?

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
C14 C9 C10 120.4(4) . . ?
C14 C9 N2 121.6(4) . . ?
C10 C9 N2 117.9(4) . . ?
C9 C10 C11 120.1(4) . . ?
C1 C6 C5 119.6(4) . . ?
C1 C6 C7 121.7(4) . . ?
C5 C6 C7 118.6(4) . . ?
C12 C11 C10 119.6(5) . . ?
C12 C11 C17 120.4(5) . . ?
C10 C11 C17 120.0(5) . . ?
C9 C14 C13 119.5(4) . . ?
C9 C14 S1 121.3(4) . . ?
C13 C14 S1 119.2(3) . . ?
C12 C13 C14 120.3(5) . . ?
C6 C1 C2 120.0(5) . . ?
C11 C12 C13 120.1(5) . . ?
C6 C5 C4 119.6(5) . . ?
C3 C4 C5 119.9(6) . . ?
C2 C3 C4 120.1(5) . . ?
C3 C2 C1 120.9(6) . . ?
O4 C7 C6 108.5(3) . . ?
O4 C7 C8 110.1(3) . . ?
C6 C7 C8 107.4(3) . . ?
O3 C8 N2 123.1(4) . . ?
O3 C8 C7 121.8(4) . . ?
N2 C8 C7 115.0(4) . . ?
C15 O4 C7 114.8(3) . . ?
O5 C15 O4 122.5(4) . . ?
O5 C15 C16 125.6(4) . . ?
O4 C15 C16 111.9(4) . . ?
O1 S1 O2 119.6(2) . . ?
O1 S1 N1 108.3(2) . . ?
O2 S1 N1 106.5(2) . . ?
O1 S1 C14 106.9(2) . . ?
O2 S1 C14 108.7(2) . . ?
N1 S1 C14 106.2(2) . . ?
C8 N2 C9 123.1(3) . . ?
C18 N1 S1 117.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        71.49
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.088


#===END
_database_code_depnum_ccdc_archive 'CCDC 992619'
