# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 N O S'
_chemical_formula_sum            'C23 H15 N O S'
_chemical_formula_weight         353.42

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   7.5420(6)
_cell_length_b                   16.0923(14)
_cell_length_c                   14.6720(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.015(2)
_cell_angle_gamma                90.00
_cell_volume                     1741.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    3153
_cell_measurement_theta_min      2.532
_cell_measurement_theta_max      23.881

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
;
The structure was solved by direct methods (Bruker, 2000) and
successive difference Fourier syntheses.
;

_diffrn_ambient_temperature      291(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 CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11702
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4001
_reflns_number_gt                2920
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  'SHELXTL (BRUKER 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0608P)²+0.2431P] 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         4001
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1129
_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 -0.1538(2) 0.33985(11) 0.91710(12) 0.0521(4) Uani 1 1 d . . .
C2 C -0.0209(2) 0.37748(11) 0.88156(11) 0.0505(4) Uani 1 1 d . . .
H2 H 0.0197 0.4311 0.8976 0.061 Uiso 1 1 calc R . .
C3 C 0.0498(2) 0.32761(10) 0.81808(11) 0.0482(4) Uani 1 1 d . . .
C4 C -0.0378(3) 0.25254(11) 0.80759(13) 0.0595(5) Uani 1 1 d . . .
H4 H -0.0113 0.2109 0.7685 0.071 Uiso 1 1 calc R . .
C5 C -0.2490(3) 0.37638(13) 0.98337(14) 0.0648(5) Uani 1 1 d . . .
H5 H -0.2193 0.4308 1.0017 0.078 Uiso 1 1 calc R . .
C6 C 0.1991(2) 0.35325(10) 0.77313(11) 0.0478(4) Uani 1 1 d . . .
C7 C 0.3147(2) 0.41756(10) 0.81049(11) 0.0483(4) Uani 1 1 d . . .
H7 H 0.2974 0.4449 0.8638 0.058 Uiso 1 1 calc R . .
C8 C 0.4559(2) 0.44123(10) 0.76861(11) 0.0456(4) Uani 1 1 d . . .
C9 C 0.4823(2) 0.39936(10) 0.68825(11) 0.0468(4) Uani 1 1 d . . .
C10 C 0.3665(2) 0.33572(10) 0.64861(12) 0.0530(4) Uani 1 1 d . . .
H10 H 0.3823 0.3089 0.5947 0.064 Uiso 1 1 calc R . .
C11 C 0.2278(2) 0.31368(11) 0.69165(12) 0.0535(4) Uani 1 1 d . . .
H11 H 0.1500 0.2710 0.6660 0.064 Uiso 1 1 calc R . .
C12 C 0.5966(2) 0.50354(10) 0.79045(11) 0.0472(4) Uani 1 1 d . . .
C13 C 0.7020(2) 0.49696(10) 0.72216(11) 0.0480(4) Uani 1 1 d . . .
C14 C 0.8571(3) 0.54466(11) 0.72581(13) 0.0564(4) Uani 1 1 d . . .
H14 H 0.9264 0.5398 0.6805 0.068 Uiso 1 1 calc R . .
C15 C 0.9043(3) 0.59934(11) 0.79907(14) 0.0625(5) Uani 1 1 d . . .
H15 H 1.0082 0.6315 0.8035 0.075 Uiso 1 1 calc R . .
C16 C 0.8007(3) 0.60777(11) 0.86640(13) 0.0615(5) Uani 1 1 d . . .
H16 H 0.8358 0.6456 0.9147 0.074 Uiso 1 1 calc R . .
C17 C 0.6462(3) 0.56067(10) 0.86273(12) 0.0550(4) Uani 1 1 d . . .
H17 H 0.5765 0.5670 0.9076 0.066 Uiso 1 1 calc R . .
C18 C 0.7015(2) 0.40973(10) 0.58083(11) 0.0463(4) Uani 1 1 d . . .
C19 C 0.7481(2) 0.32768(11) 0.57146(12) 0.0545(4) Uani 1 1 d . . .
H19 H 0.7338 0.2888 0.6163 0.065 Uiso 1 1 calc R . .
C20 C 0.8162(3) 0.30366(12) 0.49490(14) 0.0648(5) Uani 1 1 d . . .
H20 H 0.8475 0.2484 0.4882 0.078 Uiso 1 1 calc R . .
C21 C 0.8377(3) 0.36105(14) 0.42873(14) 0.0678(5) Uani 1 1 d . . .
H21 H 0.8827 0.3446 0.3771 0.081 Uiso 1 1 calc R . .
C22 C 0.7927(3) 0.44284(13) 0.43882(13) 0.0641(5) Uani 1 1 d . . .
H22 H 0.8091 0.4817 0.3943 0.077 Uiso 1 1 calc R . .
C23 C 0.7237(2) 0.46778(11) 0.51422(12) 0.0563(4) Uani 1 1 d . . .
H23 H 0.6921 0.5231 0.5204 0.068 Uiso 1 1 calc R . .
N1 N 0.6306(2) 0.43460(8) 0.65952(9) 0.0495(3) Uani 1 1 d . . .
O1 O -0.3619(2) 0.34302(11) 1.01666(13) 0.0974(5) Uani 1 1 d . . .
S1 S -0.19945(7) 0.24215(3) 0.87233(4) 0.06684(18) 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 C2 1.364(2) . ?
C1 C5 1.448(2) . ?
C1 S1 1.7111(18) . ?
C2 C3 1.415(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(2) . ?
C3 C6 1.478(2) . ?
C4 S1 1.7026(19) . ?
C4 H4 0.9300 . ?
C5 O1 1.194(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(2) . ?
C6 C11 1.410(2) . ?
C7 C8 1.389(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.408(2) . ?
C8 C12 1.447(2) . ?
C9 C10 1.393(2) . ?
C9 N1 1.395(2) . ?
C10 C11 1.376(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.395(2) . ?
C12 C13 1.406(2) . ?
C13 C14 1.391(2) . ?
C13 N1 1.391(2) . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.380(2) . ?
C18 C23 1.387(2) . ?
C18 N1 1.427(2) . ?
C19 C20 1.384(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(2) . ?
C22 H22 0.9300 . ?
C23 H23 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
C2 C1 C5 125.65(18) . . ?
C2 C1 S1 111.47(13) . . ?
C5 C1 S1 122.87(14) . . ?
C1 C2 C3 114.04(16) . . ?
C1 C2 H2 123.0 . . ?
C3 C2 H2 123.0 . . ?
C4 C3 C2 109.58(15) . . ?
C4 C3 C6 126.19(16) . . ?
C2 C3 C6 124.20(15) . . ?
C3 C4 S1 114.10(14) . . ?
C3 C4 H4 122.9 . . ?
S1 C4 H4 122.9 . . ?
O1 C5 C1 126.0(2) . . ?
O1 C5 H5 117.0 . . ?
C1 C5 H5 117.0 . . ?
C7 C6 C11 118.45(15) . . ?
C7 C6 C3 120.36(14) . . ?
C11 C6 C3 121.19(15) . . ?
C8 C7 C6 120.34(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.66(15) . . ?
C7 C8 C12 133.39(15) . . ?
C9 C8 C12 106.95(14) . . ?
C10 C9 N1 130.21(14) . . ?
C10 C9 C8 121.04(15) . . ?
N1 C9 C8 108.72(14) . . ?
C11 C10 C9 117.95(15) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C10 C11 C6 122.54(16) . . ?
C10 C11 H11 118.7 . . ?
C6 C11 H11 118.7 . . ?
C17 C12 C13 119.33(16) . . ?
C17 C12 C8 133.88(15) . . ?
C13 C12 C8 106.71(14) . . ?
C14 C13 N1 129.05(15) . . ?
C14 C13 C12 121.77(16) . . ?
N1 C13 C12 109.07(14) . . ?
C15 C14 C13 117.45(17) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C14 C15 C16 121.72(18) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 120.92(17) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C12 118.77(16) . . ?
C16 C17 H17 120.6 . . ?
C12 C17 H17 120.6 . . ?
C19 C18 C23 120.23(15) . . ?
C19 C18 N1 119.66(15) . . ?
C23 C18 N1 120.10(14) . . ?
C18 C19 C20 119.55(17) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.28(18) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.95(17) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 120.57(18) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 119.40(17) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?
C13 N1 C9 108.53(13) . . ?
C13 N1 C18 125.33(14) . . ?
C9 N1 C18 126.11(14) . . ?
C4 S1 C1 90.79(9) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 993165'
#######################################################################
#
#                 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_2



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 N O S'
_chemical_formula_sum            'C23 H15 N O S'
_chemical_formula_weight         353.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.297(6)
_cell_length_b                   14.286(7)
_cell_length_c                   10.070(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.840(7)
_cell_angle_gamma                90.00
_cell_volume                     1857.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1784
_cell_measurement_theta_min      2.526
_cell_measurement_theta_max      21.305

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
;
The structure was solved by direct methods (Bruker, 2000) and
successive difference Fourier syntheses.
;

_diffrn_ambient_temperature      291(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 CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12416
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_sigmaI/netI    0.0876
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         28.37
_reflns_number_total             4590
_reflns_number_gt                2300
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  'SHELXTL (BRUKER 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0757P)²+0.1280P] 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         4590
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1853
_refine_ls_wR_factor_gt          0.1558
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.2750(2) 0.10600(19) 0.3139(3) 0.0603(7) Uani 1 1 d . . .
C2 C 0.3343(2) 0.1700(2) 0.2648(3) 0.0719(8) Uani 1 1 d . . .
H2 H 0.3151 0.1958 0.1775 0.086 Uiso 1 1 calc R . .
C3 C 0.4278(2) 0.1929(2) 0.3607(3) 0.0661(8) Uani 1 1 d . . .
H3 H 0.4769 0.2339 0.3422 0.079 Uiso 1 1 calc R . .
C4 C 0.4383(2) 0.14795(16) 0.4842(3) 0.0513(6) Uani 1 1 d . . .
C5 C 0.1780(3) 0.0649(2) 0.2379(4) 0.0771(9) Uani 1 1 d . . .
H5 H 0.1517 0.0855 0.1488 0.093 Uiso 1 1 calc R . .
C6 C 0.52518(19) 0.15617(16) 0.6064(3) 0.0501(6) Uani 1 1 d . . .
C7 C 0.5976(2) 0.23107(17) 0.6127(3) 0.0584(7) Uani 1 1 d . . .
H7 H 0.5853 0.2753 0.5430 0.070 Uiso 1 1 calc R . .
C8 C 0.6843(2) 0.24010(18) 0.7175(3) 0.0594(7) Uani 1 1 d . . .
H8 H 0.7302 0.2895 0.7192 0.071 Uiso 1 1 calc R . .
C9 C 0.7021(2) 0.17281(17) 0.8224(3) 0.0517(6) Uani 1 1 d . . .
C10 C 0.62933(19) 0.09985(15) 0.8239(3) 0.0462(6) Uani 1 1 d . . .
C11 C 0.54214(19) 0.09177(16) 0.7153(3) 0.0479(6) Uani 1 1 d . . .
H11 H 0.4950 0.0436 0.7149 0.057 Uiso 1 1 calc R . .
C12 C 0.7694(2) 0.08573(17) 1.0105(3) 0.0517(6) Uani 1 1 d . . .
C13 C 0.6724(2) 0.04527(16) 0.9472(3) 0.0485(6) Uani 1 1 d . . .
C14 C 0.6387(2) -0.03359(18) 1.0092(3) 0.0613(7) Uani 1 1 d . . .
H14 H 0.5757 -0.0621 0.9699 0.074 Uiso 1 1 calc R . .
C15 C 0.7008(3) -0.0674(2) 1.1288(4) 0.0763(9) Uani 1 1 d . . .
H15 H 0.6780 -0.1184 1.1712 0.092 Uiso 1 1 calc R . .
C16 C 0.7969(3) -0.0277(2) 1.1887(4) 0.0799(9) Uani 1 1 d . . .
H16 H 0.8374 -0.0538 1.2683 0.096 Uiso 1 1 calc R . .
C17 C 0.8335(2) 0.0509(2) 1.1310(3) 0.0657(8) Uani 1 1 d . . .
H17 H 0.8971 0.0782 1.1708 0.079 Uiso 1 1 calc R . .
C18 C 0.8795(2) 0.21929(19) 0.9563(3) 0.0557(7) Uani 1 1 d . . .
C19 C 0.8819(3) 0.3086(2) 1.0129(4) 0.0799(10) Uani 1 1 d . . .
H19 H 0.8245 0.3322 1.0393 0.096 Uiso 1 1 calc R . .
C20 C 0.9716(3) 0.3617(2) 1.0292(4) 0.0912(11) Uani 1 1 d . . .
H20 H 0.9739 0.4211 1.0678 0.109 Uiso 1 1 calc R . .
C21 C 1.0558(3) 0.3290(3) 0.9899(4) 0.0866(11) Uani 1 1 d . . .
H21 H 1.1148 0.3660 1.0005 0.104 Uiso 1 1 calc R . .
C22 C 1.0536(3) 0.2402(3) 0.9339(4) 0.0950(12) Uani 1 1 d . . .
H22 H 1.1114 0.2168 0.9083 0.114 Uiso 1 1 calc R . .
C23 C 0.9640(2) 0.1862(2) 0.9162(4) 0.0842(10) Uani 1 1 d . . .
H23 H 0.9618 0.1271 0.8768 0.101 Uiso 1 1 calc R . .
N1 N 0.78585(16) 0.16441(15) 0.9341(2) 0.0559(6) Uani 1 1 d . . .
O1 O 0.1287(2) 0.0058(2) 0.2820(3) 0.1054(8) Uani 1 1 d . . .
S1 S 0.33316(6) 0.07461(5) 0.48048(8) 0.0616(3) 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 C2 1.375(4) . ?
C1 C5 1.456(4) . ?
C1 S1 1.730(3) . ?
C2 C3 1.417(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.478(4) . ?
C4 S1 1.740(3) . ?
C5 O1 1.216(4) . ?
C5 H5 0.9300 . ?
C6 C11 1.407(3) . ?
C6 C7 1.431(3) . ?
C7 C8 1.370(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.406(4) . ?
C8 H8 0.9300 . ?
C9 N1 1.385(3) . ?
C9 C10 1.425(3) . ?
C10 C11 1.395(4) . ?
C10 C13 1.462(4) . ?
C11 H11 0.9300 . ?
C12 C17 1.397(4) . ?
C12 N1 1.409(3) . ?
C12 C13 1.419(4) . ?
C13 C14 1.412(3) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.403(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.366(4) . ?
C18 C19 1.394(4) . ?
C18 N1 1.443(3) . ?
C19 C20 1.390(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.357(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.395(4) . ?
C22 H22 0.9300 . ?
C23 H23 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
C2 C1 C5 126.3(3) . . ?
C2 C1 S1 111.1(2) . . ?
C5 C1 S1 122.6(2) . . ?
C1 C2 C3 113.1(3) . . ?
C1 C2 H2 123.4 . . ?
C3 C2 H2 123.4 . . ?
C4 C3 C2 113.0(3) . . ?
C4 C3 H3 123.5 . . ?
C2 C3 H3 123.5 . . ?
C3 C4 C6 127.2(2) . . ?
C3 C4 S1 110.7(2) . . ?
C6 C4 S1 122.01(19) . . ?
O1 C5 C1 125.1(3) . . ?
O1 C5 H5 117.4 . . ?
C1 C5 H5 117.4 . . ?
C11 C6 C7 118.3(2) . . ?
C11 C6 C4 123.0(2) . . ?
C7 C6 C4 118.7(2) . . ?
C8 C7 C6 122.6(2) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 118.3(2) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
N1 C9 C8 128.9(2) . . ?
N1 C9 C10 110.1(2) . . ?
C8 C9 C10 121.0(2) . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 C13 134.8(2) . . ?
C9 C10 C13 105.7(2) . . ?
C10 C11 C6 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C17 C12 N1 128.1(3) . . ?
C17 C12 C13 123.1(2) . . ?
N1 C12 C13 108.8(2) . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 C10 134.4(3) . . ?
C12 C13 C10 107.1(2) . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 122.1(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C12 C17 C16 116.4(3) . . ?
C12 C17 H17 121.8 . . ?
C16 C17 H17 121.8 . . ?
C23 C18 C19 119.8(3) . . ?
C23 C18 N1 120.4(2) . . ?
C19 C18 N1 119.7(2) . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 119.7(3) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 119.5(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C22 120.6(3) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C9 N1 C12 108.3(2) . . ?
C9 N1 C18 125.1(2) . . ?
C12 N1 C18 126.1(2) . . ?
C1 S1 C4 92.03(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
C5 C1 C2 C3 -176.5(3) . . . . ?
S1 C1 C2 C3 1.0(3) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C2 C3 C4 C6 -179.6(2) . . . . ?
C2 C3 C4 S1 1.5(3) . . . . ?
C2 C1 C5 O1 177.2(3) . . . . ?
S1 C1 C5 O1 0.1(5) . . . . ?
C3 C4 C6 C11 -163.9(3) . . . . ?
S1 C4 C6 C11 14.9(3) . . . . ?
C3 C4 C6 C7 13.9(4) . . . . ?
S1 C4 C6 C7 -167.23(18) . . . . ?
C11 C6 C7 C8 2.6(4) . . . . ?
C4 C6 C7 C8 -175.3(2) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C7 C8 C9 N1 176.5(3) . . . . ?
C7 C8 C9 C10 -3.3(4) . . . . ?
N1 C9 C10 C11 -175.9(2) . . . . ?
C8 C9 C10 C11 3.9(4) . . . . ?
N1 C9 C10 C13 1.1(3) . . . . ?
C8 C9 C10 C13 -179.1(2) . . . . ?
C9 C10 C11 C6 -1.2(3) . . . . ?
C13 C10 C11 C6 -177.1(2) . . . . ?
C7 C6 C11 C10 -2.0(3) . . . . ?
C4 C6 C11 C10 175.9(2) . . . . ?
C17 C12 C13 C14 0.4(4) . . . . ?
N1 C12 C13 C14 -178.3(2) . . . . ?
C17 C12 C13 C10 -179.3(2) . . . . ?
N1 C12 C13 C10 2.0(3) . . . . ?
C11 C10 C13 C14 -5.2(5) . . . . ?
C9 C10 C13 C14 178.5(3) . . . . ?
C11 C10 C13 C12 174.4(3) . . . . ?
C9 C10 C13 C12 -1.9(3) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C10 C13 C14 C15 -179.9(3) . . . . ?
C13 C14 C15 C16 -1.6(5) . . . . ?
C14 C15 C16 C17 1.8(5) . . . . ?
N1 C12 C17 C16 178.2(3) . . . . ?
C13 C12 C17 C16 -0.3(4) . . . . ?
C15 C16 C17 C12 -0.8(5) . . . . ?
C23 C18 C19 C20 -1.0(5) . . . . ?
N1 C18 C19 C20 -177.8(3) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C19 C20 C21 C22 -0.9(6) . . . . ?
C20 C21 C22 C23 1.2(6) . . . . ?
C19 C18 C23 C22 1.3(5) . . . . ?
N1 C18 C23 C22 178.1(3) . . . . ?
C21 C22 C23 C18 -1.4(6) . . . . ?
C8 C9 N1 C12 -179.7(2) . . . . ?
C10 C9 N1 C12 0.1(3) . . . . ?
C8 C9 N1 C18 -7.5(4) . . . . ?
C10 C9 N1 C18 172.2(2) . . . . ?
C17 C12 N1 C9 -180.0(3) . . . . ?
C13 C12 N1 C9 -1.3(3) . . . . ?
C17 C12 N1 C18 8.0(4) . . . . ?
C13 C12 N1 C18 -173.4(2) . . . . ?
C23 C18 N1 C9 -94.6(3) . . . . ?
C19 C18 N1 C9 82.2(4) . . . . ?
C23 C18 N1 C12 76.1(4) . . . . ?
C19 C18 N1 C12 -107.1(3) . . . . ?
C2 C1 S1 C4 -0.1(2) . . . . ?
C5 C1 S1 C4 177.5(2) . . . . ?
C3 C4 S1 C1 -0.8(2) . . . . ?
C6 C4 S1 C1 -179.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 993166'
#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H23 N3 O3 S'
_chemical_formula_sum            'C29 H23 N3 O3 S'
_chemical_formula_weight         493.56

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'
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                   9.090(5)
_cell_length_b                   9.383(5)
_cell_length_c                   15.108(8)
_cell_angle_alpha                79.476(9)
_cell_angle_beta                 81.970(8)
_cell_angle_gamma                81.163(9)
_cell_volume                     1243.6(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1741
_cell_measurement_theta_min      2.283
_cell_measurement_theta_max      25.419

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
; 
The structure was solved by direct methods (Bruker, 2000) and
successive difference Fourier syntheses. 
;

_diffrn_ambient_temperature      291(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 CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8356
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         27.55
_reflns_number_total             5657
_reflns_number_gt                3278
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  'SHELXTL (BRUKER 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0627P)²] 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         5657
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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 -0.3504(3) 0.3610(3) -0.07710(16) 0.0486(6) Uani 1 1 d . . .
C2 C -0.2822(3) 0.4421(2) -0.02093(15) 0.0431(5) Uani 1 1 d . . .
C3 C -0.2099(3) 0.3486(2) 0.05049(16) 0.0477(6) Uani 1 1 d . . .
C4 C -0.2879(3) 0.5892(2) -0.03433(14) 0.0443(5) Uani 1 1 d . . .
H4 H -0.3383 0.6393 -0.0826 0.053 Uiso 1 1 calc R . .
C5 C -0.2274(3) 0.6792(2) 0.01505(14) 0.0412(5) Uani 1 1 d . . .
C6 C -0.2355(3) 0.8295(2) -0.00472(15) 0.0491(6) Uani 1 1 d . . .
H6 H -0.2830 0.8855 -0.0526 0.059 Uiso 1 1 calc R . .
C7 C -0.1660(3) 0.8902(2) 0.05350(15) 0.0474(6) Uani 1 1 d . . .
H7 H -0.1616 0.9898 0.0480 0.057 Uiso 1 1 calc R . .
C8 C -0.1048(2) 0.7867(2) 0.11997(14) 0.0397(5) Uani 1 1 d . . .
C9 C -0.0277(3) 0.8064(2) 0.19566(14) 0.0414(5) Uani 1 1 d . . .
C10 C -0.0069(3) 0.6910(2) 0.26853(15) 0.0508(6) Uani 1 1 d . . .
H10 H -0.0408 0.6029 0.2673 0.061 Uiso 1 1 calc R . .
C11 C 0.0618(3) 0.7042(2) 0.34137(15) 0.0524(6) Uani 1 1 d . . .
H11 H 0.0739 0.6269 0.3891 0.063 Uiso 1 1 calc R . .
C12 C 0.1125(3) 0.8358(2) 0.34190(14) 0.0419(5) Uani 1 1 d . . .
C13 C 0.0914(2) 0.9547(2) 0.27064(14) 0.0389(5) Uani 1 1 d . . .
C14 C 0.0217(2) 0.9383(2) 0.19734(14) 0.0407(5) Uani 1 1 d . . .
H14 H 0.0084 1.0155 0.1497 0.049 Uiso 1 1 calc R . .
C15 C 0.1505(2) 1.0752(2) 0.29440(14) 0.0411(5) Uani 1 1 d . . .
C16 C 0.2043(3) 1.0253(2) 0.37885(15) 0.0432(5) Uani 1 1 d . . .
C17 C 0.2686(3) 1.1161(3) 0.42157(17) 0.0565(7) Uani 1 1 d . . .
H17 H 0.3062 1.0819 0.4768 0.068 Uiso 1 1 calc R . .
C18 C 0.2742(3) 1.2585(3) 0.37871(18) 0.0654(7) Uani 1 1 d . . .
H18 H 0.3171 1.3212 0.4056 0.078 Uiso 1 1 calc R . .
C19 C 0.2178(3) 1.3107(3) 0.29658(18) 0.0618(7) Uani 1 1 d . . .
H19 H 0.2219 1.4078 0.2700 0.074 Uiso 1 1 calc R . .
C20 C 0.1557(3) 1.2205(2) 0.25390(16) 0.0499(6) Uani 1 1 d . . .
H20 H 0.1178 1.2560 0.1989 0.060 Uiso 1 1 calc R . .
C21 C 0.2202(3) 0.7892(2) 0.48979(15) 0.0446(6) Uani 1 1 d . . .
C22 C 0.3011(3) 0.6518(3) 0.48834(17) 0.0580(7) Uani 1 1 d . . .
H22 H 0.3330 0.6190 0.4335 0.070 Uiso 1 1 calc R . .
C23 C 0.3340(3) 0.5642(3) 0.56846(19) 0.0707(8) Uani 1 1 d . . .
H23 H 0.3859 0.4708 0.5677 0.085 Uiso 1 1 calc R . .
C24 C 0.2904(3) 0.6140(3) 0.65004(19) 0.0693(8) Uani 1 1 d . . .
H24 H 0.3145 0.5552 0.7040 0.083 Uiso 1 1 calc R . .
C25 C 0.2113(3) 0.7508(3) 0.65104(16) 0.0634(7) Uani 1 1 d . . .
H25 H 0.1825 0.7848 0.7058 0.076 Uiso 1 1 calc R . .
C26 C 0.1744(3) 0.8381(3) 0.57122(15) 0.0516(6) Uani 1 1 d . . .
H26 H 0.1189 0.9298 0.5724 0.062 Uiso 1 1 calc R . .
C27 C 0.5077(3) 0.8308(3) 0.21686(18) 0.0579(7) Uani 1 1 d . . .
H27 H 0.4756 0.8627 0.1599 0.069 Uiso 1 1 calc R . .
C28 C 0.6134(3) 0.8851(3) 0.34291(18) 0.0734(8) Uani 1 1 d . . .
H28A H 0.5918 0.7883 0.3692 0.110 Uiso 1 1 calc R . .
H28B H 0.5646 0.9529 0.3817 0.110 Uiso 1 1 calc R . .
H28C H 0.7197 0.8870 0.3362 0.110 Uiso 1 1 calc R . .
C29 C 0.5688(4) 1.0742(3) 0.2082(2) 0.0784(9) Uani 1 1 d . . .
H29A H 0.5392 1.0848 0.1486 0.118 Uiso 1 1 calc R . .
H29B H 0.6701 1.0947 0.2037 0.118 Uiso 1 1 calc R . .
H29C H 0.5036 1.1414 0.2417 0.118 Uiso 1 1 calc R . .
N1 N -0.1498(3) 0.2739(2) 0.10705(15) 0.0682(7) Uani 1 1 d . . .
N2 N 0.1823(2) 0.87899(19) 0.40693(12) 0.0460(5) Uani 1 1 d . . .
N3 N 0.5591(2) 0.9258(2) 0.25472(14) 0.0554(5) Uani 1 1 d . . .
O1 O -0.3512(2) 0.23043(18) -0.05803(13) 0.0711(5) Uani 1 1 d . . .
O2 O -0.4078(2) 0.44571(18) -0.14642(11) 0.0644(5) Uani 1 1 d . . .
H2 H -0.4312 0.3951 -0.1798 0.097 Uiso 1 1 calc R . .
O3 O 0.4991(2) 0.7010(2) 0.25203(12) 0.0705(5) Uani 1 1 d . . .
S1 S -0.13094(7) 0.61390(6) 0.10791(4) 0.04607(19) 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 O1 1.207(3) . ?
C1 O2 1.312(3) . ?
C1 C2 1.487(3) . ?
C2 C4 1.352(3) . ?
C2 C3 1.428(3) . ?
C3 N1 1.146(3) . ?
C4 C5 1.435(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 S1 1.726(2) . ?
C6 C7 1.394(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.474(3) . ?
C8 S1 1.720(2) . ?
C9 C14 1.385(3) . ?
C9 C10 1.407(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C12 N2 1.389(3) . ?
C12 C13 1.412(3) . ?
C13 C14 1.393(3) . ?
C13 C15 1.444(3) . ?
C14 H14 0.9300 . ?
C15 C20 1.394(3) . ?
C15 C16 1.404(3) . ?
C16 C17 1.393(3) . ?
C16 N2 1.397(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.379(3) . ?
C21 C22 1.385(3) . ?
C21 N2 1.429(3) . ?
C22 C23 1.376(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 O3 1.247(3) . ?
C27 N3 1.314(3) . ?
C27 H27 0.9300 . ?
C28 N3 1.451(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N3 1.451(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
O2 H2 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
O1 C1 O2 125.4(2) . . ?
O1 C1 C2 121.4(2) . . ?
O2 C1 C2 113.2(2) . . ?
C4 C2 C3 122.5(2) . . ?
C4 C2 C1 124.3(2) . . ?
C3 C2 C1 113.2(2) . . ?
N1 C3 C2 179.0(3) . . ?
C2 C4 C5 129.4(2) . . ?
C2 C4 H4 115.3 . . ?
C5 C4 H4 115.3 . . ?
C6 C5 C4 125.6(2) . . ?
C6 C5 S1 109.79(16) . . ?
C4 C5 S1 124.58(17) . . ?
C5 C6 C7 114.1(2) . . ?
C5 C6 H6 123.0 . . ?
C7 C6 H6 123.0 . . ?
C8 C7 C6 112.8(2) . . ?
C8 C7 H7 123.6 . . ?
C6 C7 H7 123.6 . . ?
C7 C8 C9 129.4(2) . . ?
C7 C8 S1 110.85(16) . . ?
C9 C8 S1 119.71(15) . . ?
C14 C9 C10 119.2(2) . . ?
C14 C9 C8 120.99(18) . . ?
C10 C9 C8 119.8(2) . . ?
C11 C10 C9 122.2(2) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 118.2(2) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C11 C12 N2 130.0(2) . . ?
C11 C12 C13 121.2(2) . . ?
N2 C12 C13 108.79(19) . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 C15 133.71(19) . . ?
C12 C13 C15 106.84(18) . . ?
C9 C14 C13 119.76(19) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C20 C15 C16 119.4(2) . . ?
C20 C15 C13 133.6(2) . . ?
C16 C15 C13 106.96(18) . . ?
C17 C16 N2 129.6(2) . . ?
C17 C16 C15 121.6(2) . . ?
N2 C16 C15 108.86(19) . . ?
C18 C17 C16 117.4(2) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 C19 121.8(2) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C15 119.0(2) . . ?
C19 C20 H20 120.5 . . ?
C15 C20 H20 120.5 . . ?
C26 C21 C22 120.0(2) . . ?
C26 C21 N2 120.2(2) . . ?
C22 C21 N2 119.8(2) . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 119.7(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 119.9(2) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
O3 C27 N3 124.5(2) . . ?
O3 C27 H27 117.7 . . ?
N3 C27 H27 117.7 . . ?
N3 C28 H28A 109.5 . . ?
N3 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N3 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C12 N2 C16 108.54(17) . . ?
C12 N2 C21 125.25(19) . . ?
C16 N2 C21 126.18(19) . . ?
C27 N3 C28 121.5(2) . . ?
C27 N3 C29 121.1(2) . . ?
C28 N3 C29 117.4(2) . . ?
C1 O2 H2 109.5 . . ?
C8 S1 C5 92.53(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
O1 C1 C2 C4 -174.6(2) . . . . ?
O2 C1 C2 C4 5.0(4) . . . . ?
O1 C1 C2 C3 4.9(4) . . . . ?
O2 C1 C2 C3 -175.6(2) . . . . ?
C4 C2 C3 N1 -79(14) . . . . ?
C1 C2 C3 N1 102(14) . . . . ?
C3 C2 C4 C5 0.4(4) . . . . ?
C1 C2 C4 C5 179.8(2) . . . . ?
C2 C4 C5 C6 178.4(2) . . . . ?
C2 C4 C5 S1 -0.7(4) . . . . ?
C4 C5 C6 C7 -179.3(2) . . . . ?
S1 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C9 -177.5(2) . . . . ?
C6 C7 C8 S1 1.2(3) . . . . ?
C7 C8 C9 C14 -14.4(4) . . . . ?
S1 C8 C9 C14 166.96(17) . . . . ?
C7 C8 C9 C10 164.1(2) . . . . ?
S1 C8 C9 C10 -14.5(3) . . . . ?
C14 C9 C10 C11 -0.4(4) . . . . ?
C8 C9 C10 C11 -178.9(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 N2 178.7(2) . . . . ?
C10 C11 C12 C13 1.5(4) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
N2 C12 C13 C14 -179.4(2) . . . . ?
C11 C12 C13 C15 177.4(2) . . . . ?
N2 C12 C13 C15 -0.4(3) . . . . ?
C10 C9 C14 C13 0.2(3) . . . . ?
C8 C9 C14 C13 178.7(2) . . . . ?
C12 C13 C14 C9 0.8(3) . . . . ?
C15 C13 C14 C9 -177.9(2) . . . . ?
C14 C13 C15 C20 2.2(5) . . . . ?
C12 C13 C15 C20 -176.6(2) . . . . ?
C14 C13 C15 C16 178.6(2) . . . . ?
C12 C13 C15 C16 -0.3(3) . . . . ?
C20 C15 C16 C17 -2.7(4) . . . . ?
C13 C15 C16 C17 -179.7(2) . . . . ?
C20 C15 C16 N2 177.8(2) . . . . ?
C13 C15 C16 N2 0.8(3) . . . . ?
N2 C16 C17 C18 -179.1(2) . . . . ?
C15 C16 C17 C18 1.5(4) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 C20 -1.1(5) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C16 C15 C20 C19 1.9(4) . . . . ?
C13 C15 C20 C19 178.0(3) . . . . ?
C26 C21 C22 C23 0.7(4) . . . . ?
N2 C21 C22 C23 -178.3(2) . . . . ?
C21 C22 C23 C24 -1.8(4) . . . . ?
C22 C23 C24 C25 1.2(4) . . . . ?
C23 C24 C25 C26 0.4(4) . . . . ?
C22 C21 C26 C25 0.9(4) . . . . ?
N2 C21 C26 C25 180.0(2) . . . . ?
C24 C25 C26 C21 -1.5(4) . . . . ?
C11 C12 N2 C16 -176.6(2) . . . . ?
C13 C12 N2 C16 0.9(3) . . . . ?
C11 C12 N2 C21 1.5(4) . . . . ?
C13 C12 N2 C21 179.0(2) . . . . ?
C17 C16 N2 C12 179.5(3) . . . . ?
C15 C16 N2 C12 -1.0(3) . . . . ?
C17 C16 N2 C21 1.4(4) . . . . ?
C15 C16 N2 C21 -179.1(2) . . . . ?
C26 C21 N2 C12 -127.3(3) . . . . ?
C22 C21 N2 C12 51.8(3) . . . . ?
C26 C21 N2 C16 50.5(3) . . . . ?
C22 C21 N2 C16 -130.4(3) . . . . ?
O3 C27 N3 C28 0.8(4) . . . . ?
O3 C27 N3 C29 178.5(3) . . . . ?
C7 C8 S1 C5 -1.10(19) . . . . ?
C9 C8 S1 C5 177.75(19) . . . . ?
C6 C5 S1 C8 0.69(19) . . . . ?
C4 C5 S1 C8 179.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.043

#===END
_database_code_depnum_ccdc_archive 'CCDC 993167'
