# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Hans-Joachim Knolker'
_publ_contact_author_email       HANS-JOACHIM.KNOELKER@TU-DRESDEN.DE

_publ_section_title              
;
First total synthesis of clausine L and pityriazole, a
metabolite of the human pathogenic yeast Malassezia furfur
;
loop_
_publ_author_name
'Hans-Joachim Knolker'
'Ronny Forke'
'Anne Jager'

# Attachment 'an50.cif'

data_an50
_database_code_depnum_ccdc_archive 'CCDC 683126'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_int_tables_number      33

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

_cell_length_a                   14.127(1)
_cell_length_b                   11.910(2)
_cell_length_c                   7.618(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1281.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    198(2)
_cell_measurement_reflns_used    379
_cell_measurement_theta_min      4.193
_cell_measurement_theta_max      24.129

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'

_publ_section_references         
;
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
These references have to be cited in the publication, because they named
software was used for measurement, evaluation of data, solution, refinement
and computing the publication material of the structure.
They are in ACTACC-format and need to be changed for publication in another
journal.
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

<enCIFer>
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004).
J. Appl. Cryst. 37, 331-334.

<SIR2004>
Burla, M. C., Caliandro, R.,Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori,
G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.

<Dirax/LSQ>
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.

<EVALCCD>
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst. 36, 220-229.

<ORTEP-3 for Windows>
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

<WinGX>
Farrugia, L. J. (1999). WinGX. J. Appl. Cryst. 32, 837-838.

<CIF-Format>
Hall, S. R., Allen, F. H. & Brown, I. D. (1991). Acta Cryst. A47, 655-685.

<COLLECT>
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.

<SHELX97-2>
Sheldrick, G. M. (1997). SHELX97. Programs for Crystal Structure Analysis
(Release 97-2). University of G\"ottingen, Germany.

<SADABS 2.10>
Sheldrick, G. M. (2002). SADABS, Version 2.10, Bruker Analytical X-Ray Systems,
Inc.: Madison, WI.

<PLATON>
Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool. Utrecht
University, Utrecht, The Netherlands.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      198(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       \f
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7318
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         25.40
_reflns_number_total             2201
_reflns_number_gt                1582
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0397P)^2^+0.1664P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(18)
_refine_ls_number_reflns         2201
_refine_ls_number_parameters     178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.7334(2) 0.7932(3) 0.1341(4) 0.0393(7) Uani 1 1 d . . .
H1 H 0.7919 0.7863 0.0734 0.047 Uiso 1 1 calc R . .
C2 C 0.6904(2) 0.7022(2) 0.2102(4) 0.0372(7) Uani 1 1 d . . .
C3 C 0.6012(2) 0.7107(2) 0.2943(4) 0.0348(7) Uani 1 1 d . . .
C4 C 0.5572(2) 0.8141(2) 0.3071(4) 0.0340(7) Uani 1 1 d . . .
H4 H 0.4974 0.8205 0.3632 0.041 Uiso 1 1 calc R . .
C4A C 0.6007(2) 0.9077(2) 0.2379(4) 0.0332(7) Uani 1 1 d . . .
C4B C 0.5789(2) 1.0267(2) 0.2367(4) 0.0382(7) Uani 1 1 d . . .
C5 C 0.5075(2) 1.0902(2) 0.3125(5) 0.0472(8) Uani 1 1 d . . .
H5 H 0.4559 1.0551 0.3708 0.057 Uiso 1 1 calc R . .
C6 C 0.5134(3) 1.2058(3) 0.3010(5) 0.0585(10) Uani 1 1 d . . .
H6 H 0.4652 1.2510 0.3518 0.070 Uiso 1 1 calc R . .
C7 C 0.5886(3) 1.2564(3) 0.2165(5) 0.0653(11) Uani 1 1 d . . .
H7 H 0.5922 1.3360 0.2152 0.078 Uiso 1 1 calc R . .
C8 C 0.6588(3) 1.1959(3) 0.1339(5) 0.0567(10) Uani 1 1 d . . .
H8 H 0.7084 1.2318 0.0713 0.068 Uiso 1 1 calc R . .
C8A C 0.6534(2) 1.0792(2) 0.1467(4) 0.0439(8) Uani 1 1 d . . .
N9 N 0.7172(2) 0.9989(2) 0.0902(4) 0.0453(7) Uani 1 1 d . . .
C9A C 0.6876(2) 0.8958(2) 0.1498(4) 0.0376(7) Uani 1 1 d . . .
O10 O 0.72848(15) 0.59621(16) 0.2090(3) 0.0467(6) Uani 1 1 d . . .
C10 C 0.8154(2) 0.5806(3) 0.1152(5) 0.0618(10) Uani 1 1 d . . .
H10A H 0.8657 0.6244 0.1715 0.093 Uiso 1 1 calc R . .
H10B H 0.8075 0.6058 -0.0063 0.093 Uiso 1 1 calc R . .
H10C H 0.8325 0.5008 0.1163 0.093 Uiso 1 1 calc R . .
C11 C 0.5536(2) 0.6103(2) 0.3679(4) 0.0365(7) Uani 1 1 d . . .
O11 O 0.59168(15) 0.53367(18) 0.4441(3) 0.0555(7) Uani 1 1 d . . .
O12 O 0.46045(15) 0.61190(15) 0.3377(3) 0.0427(6) Uani 1 1 d . . .
C12 C 0.4066(2) 0.5184(3) 0.4035(5) 0.0521(9) Uani 1 1 d . . .
H12A H 0.4251 0.5031 0.5251 0.078 Uiso 1 1 calc R . .
H12B H 0.4192 0.4520 0.3312 0.078 Uiso 1 1 calc R . .
H12C H 0.3390 0.5364 0.3990 0.078 Uiso 1 1 calc R . .
H9 H 0.770(2) 1.012(2) 0.035(4) 0.039(9) Uiso 1 1 d . . .

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
C1 0.0293(15) 0.0549(19) 0.0336(17) 0.0010(16) 0.0039(15) -0.0032(14)
C2 0.0354(16) 0.0434(17) 0.0328(17) -0.0011(15) -0.0023(15) 0.0048(14)
C3 0.0382(17) 0.0354(17) 0.0309(15) 0.0017(13) -0.0035(14) 0.0006(13)
C4 0.0318(15) 0.0378(16) 0.0325(17) 0.0020(13) 0.0008(14) -0.0032(12)
C4A 0.0351(17) 0.0365(15) 0.0281(15) 0.0029(13) -0.0021(14) -0.0034(13)
C4B 0.0502(18) 0.0359(15) 0.0286(15) 0.0030(14) -0.0033(14) -0.0054(15)
C5 0.063(2) 0.0403(18) 0.0386(18) 0.0022(14) 0.0034(19) 0.0013(16)
C6 0.093(3) 0.041(2) 0.041(2) 0.0023(16) -0.001(2) 0.0071(19)
C7 0.104(3) 0.0373(18) 0.054(2) 0.0039(19) -0.006(3) -0.002(2)
C8 0.087(3) 0.041(2) 0.0418(19) 0.0114(17) -0.008(2) -0.0176(19)
C8A 0.059(2) 0.0446(19) 0.0275(16) 0.0030(15) -0.0071(17) -0.0094(17)
N9 0.0442(16) 0.0493(16) 0.0425(17) 0.0069(12) 0.0053(15) -0.0124(14)
C9A 0.0373(16) 0.0415(18) 0.0341(17) 0.0057(15) -0.0029(14) -0.0088(14)
O10 0.0475(13) 0.0455(12) 0.0471(13) 0.0019(10) 0.0093(12) 0.0116(10)
C10 0.045(2) 0.076(3) 0.065(3) -0.001(2) 0.0114(19) 0.0196(17)
C11 0.0413(19) 0.0357(16) 0.0324(17) 0.0013(13) 0.0021(14) 0.0008(14)
O11 0.0488(13) 0.0491(13) 0.0685(16) 0.0248(12) -0.0048(13) 0.0013(11)
O12 0.0399(12) 0.0400(12) 0.0481(14) 0.0079(10) -0.0006(11) -0.0059(10)
C12 0.053(2) 0.0432(19) 0.060(2) 0.0075(16) -0.002(2) -0.0146(16)

_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 1.372(4) . ?
C1 C9A 1.389(4) . ?
C1 H1 0.9500 . ?
C2 O10 1.372(3) . ?
C2 C3 1.417(4) . ?
C3 C4 1.382(4) . ?
C3 C11 1.482(4) . ?
C4 C4A 1.377(4) . ?
C4 H4 0.9500 . ?
C4A C9A 1.406(4) . ?
C4A C4B 1.451(4) . ?
C4B C5 1.387(4) . ?
C4B C8A 1.403(5) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(5) . ?
C7 H7 0.9500 . ?
C8 C8A 1.395(4) . ?
C8 H8 0.9500 . ?
C8A N9 1.383(4) . ?
N9 C9A 1.374(4) . ?
N9 H9 0.87(3) . ?
O10 C10 1.433(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O11 1.208(3) . ?
C11 O12 1.336(4) . ?
O12 C12 1.439(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 C9A 116.9(3) . . ?
C2 C1 H1 121.6 . . ?
C9A C1 H1 121.6 . . ?
C1 C2 O10 123.4(3) . . ?
C1 C2 C3 121.9(3) . . ?
O10 C2 C3 114.7(2) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 C11 119.2(3) . . ?
C2 C3 C11 121.1(2) . . ?
C4A C4 C3 119.6(3) . . ?
C4A C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C4A C9A 119.4(3) . . ?
C4 C4A C4B 134.3(3) . . ?
C9A C4A C4B 106.2(2) . . ?
C5 C4B C8A 120.5(3) . . ?
C5 C4B C4A 133.2(3) . . ?
C8A C4B C4A 106.2(3) . . ?
C6 C5 C4B 118.2(3) . . ?
C6 C5 H5 120.9 . . ?
C4B C5 H5 120.9 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 122.6(3) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C8A 116.8(3) . . ?
C7 C8 H8 121.6 . . ?
C8A C8 H8 121.6 . . ?
N9 C8A C8 129.2(3) . . ?
N9 C8A C4B 109.5(3) . . ?
C8 C8A C4B 121.2(3) . . ?
C9A N9 C8A 108.5(3) . . ?
C9A N9 H9 125.5(19) . . ?
C8A N9 H9 125.8(19) . . ?
N9 C9A C1 128.0(3) . . ?
N9 C9A C4A 109.5(3) . . ?
C1 C9A C4A 122.4(2) . . ?
C2 O10 C10 117.3(2) . . ?
O10 C10 H10A 109.5 . . ?
O10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O10 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O11 C11 O12 122.2(3) . . ?
O11 C11 C3 126.1(3) . . ?
O12 C11 C3 111.7(3) . . ?
C11 O12 C12 116.7(2) . . ?
O12 C12 H12A 109.5 . . ?
O12 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O12 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 C2 O10 -178.3(3) . . . . ?
C9A C1 C2 C3 2.8(4) . . . . ?
C1 C2 C3 C4 -2.7(4) . . . . ?
O10 C2 C3 C4 178.4(3) . . . . ?
C1 C2 C3 C11 176.9(3) . . . . ?
O10 C2 C3 C11 -2.1(4) . . . . ?
C2 C3 C4 C4A 0.0(4) . . . . ?
C11 C3 C4 C4A -179.5(3) . . . . ?
C3 C4 C4A C9A 2.3(4) . . . . ?
C3 C4 C4A C4B -175.6(3) . . . . ?
C4 C4A C4B C5 3.4(6) . . . . ?
C9A C4A C4B C5 -174.7(3) . . . . ?
C4 C4A C4B C8A 178.6(3) . . . . ?
C9A C4A C4B C8A 0.5(3) . . . . ?
C8A C4B C5 C6 -1.8(5) . . . . ?
C4A C4B C5 C6 172.9(3) . . . . ?
C4B C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 C8 2.8(6) . . . . ?
C6 C7 C8 C8A -3.2(6) . . . . ?
C7 C8 C8A N9 -174.1(3) . . . . ?
C7 C8 C8A C4B 1.2(5) . . . . ?
C5 C4B C8A N9 177.4(3) . . . . ?
C4A C4B C8A N9 1.5(3) . . . . ?
C5 C4B C8A C8 1.3(5) . . . . ?
C4A C4B C8A C8 -174.7(3) . . . . ?
C8 C8A N9 C9A 172.8(3) . . . . ?
C4B C8A N9 C9A -3.0(3) . . . . ?
C8A N9 C9A C1 -175.3(3) . . . . ?
C8A N9 C9A C4A 3.3(3) . . . . ?
C2 C1 C9A N9 177.9(3) . . . . ?
C2 C1 C9A C4A -0.5(4) . . . . ?
C4 C4A C9A N9 179.3(3) . . . . ?
C4B C4A C9A N9 -2.3(3) . . . . ?
C4 C4A C9A C1 -2.1(4) . . . . ?
C4B C4A C9A C1 176.3(3) . . . . ?
C1 C2 O10 C10 -3.2(4) . . . . ?
C3 C2 O10 C10 175.7(3) . . . . ?
C4 C3 C11 O11 -141.4(3) . . . . ?
C2 C3 C11 O11 39.0(5) . . . . ?
C4 C3 C11 O12 39.7(4) . . . . ?
C2 C3 C11 O12 -139.8(3) . . . . ?
O11 C11 O12 C12 1.2(4) . . . . ?
C3 C11 O12 C12 -180.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042
_chemical_compound_source        synthesis

# Attachment 'an59.cif'

data_an59
_database_code_depnum_ccdc_archive 'CCDC 683127'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N2 O5 S'
_chemical_formula_sum            'C28 H20 N2 O5 S'
_chemical_formula_weight         496.52

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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_int_tables_number      14

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                   12.061(1)
_cell_length_b                   22.545(1)
_cell_length_c                   9.161(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.45(1)
_cell_angle_gamma                90.00
_cell_volume                     2376.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    308
_cell_measurement_theta_min      4.031?
_cell_measurement_theta_max      21.500

_exptl_crystal_description       needle
_exptl_crystal_colour            'light grey'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8976
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'

_publ_section_references         
;
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
These references have to be cited in the publication, because they named
software was used for measurement, evaluation of data, solution, refinement
and computing the publication material of the structure.
They are in ACTACC-format and need to be changed for publication in another
journal.
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

<enCIFer>
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004).
J. Appl. Cryst. 37, 331-334.

<SIR2004>
Burla, M. C., Caliandro, R.,Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori,
G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.

<Dirax/LSQ>
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.

<EVALCCD>
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst. 36, 220-229.

<ORTEP-3 for Windows>
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

<WinGX>
Farrugia, L. J. (1999). WinGX. J. Appl. Cryst. 32, 837-838.

<CIF-Format>
Hall, S. R., Allen, F. H. & Brown, I. D. (1991). Acta Cryst. A47, 655-685.

<COLLECT>
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.

<SHELX97-2>
Sheldrick, G. M. (1997). SHELX97. Programs for Crystal Structure Analysis
(Release 97-2). University of G\"ottingen, Germany.

<SADABS 2.10>
Sheldrick, G. M. (2002). SADABS, Version 2.10, Bruker Analytical X-Ray Systems,
Inc.: Madison, WI.

<PLATON>
Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool. Utrecht
University, Utrecht, The Netherlands.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       \f
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36307
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5184
_reflns_number_gt                3315
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0437P)^2^+1.2622P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5184
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.29822(18) 0.01353(9) 0.9813(2) 0.0349(5) Uani 1 1 d . . .
C2 C 0.3740(2) 0.04577(10) 1.1001(3) 0.0382(5) Uani 1 1 d . . .
O2 O 0.35850(15) 0.10523(7) 1.0974(2) 0.0558(5) Uani 1 1 d . . .
H2 H 0.4098 0.1205 1.1672 0.084 Uiso 1 1 calc R . .
C3 C 0.46350(19) 0.01784(10) 1.2166(3) 0.0371(5) Uani 1 1 d . . .
C10 C 0.5400(2) 0.05429(11) 1.3370(3) 0.0431(6) Uani 1 1 d . . .
O4 O 0.62186(13) 0.02427(7) 1.44016(19) 0.0494(4) Uani 1 1 d . . .
O3 O 0.53243(17) 0.10831(8) 1.3447(2) 0.0686(6) Uani 1 1 d . . .
C11 C 0.7050(2) 0.05918(13) 1.5554(3) 0.0614(8) Uani 1 1 d . . .
H11A H 0.7527 0.0815 1.5081 0.092 Uiso 1 1 calc R . .
H11B H 0.7531 0.0333 1.6315 0.092 Uiso 1 1 calc R . .
H11C H 0.6642 0.0859 1.6028 0.092 Uiso 1 1 calc R . .
C4 C 0.47609(18) -0.04366(10) 1.2144(2) 0.0365(5) Uani 1 1 d . . .
H4 H 0.5340 -0.0623 1.2913 0.044 Uiso 1 1 calc R . .
C4A C 0.40318(18) -0.07678(9) 1.0990(2) 0.0340(5) Uani 1 1 d . . .
C4B C 0.38879(19) -0.13957(9) 1.0670(3) 0.0371(5) Uani 1 1 d . . .
C5 C 0.4393(2) -0.19043(10) 1.1447(3) 0.0474(6) Uani 1 1 d . . .
H5 H 0.4995 -0.1877 1.2358 0.057 Uiso 1 1 calc R . .
C6 C 0.3985(2) -0.24513(11) 1.0843(3) 0.0555(7) Uani 1 1 d . . .
H6 H 0.4301 -0.2795 1.1366 0.067 Uiso 1 1 calc R . .
C7 C 0.3106(2) -0.24938(11) 0.9462(3) 0.0569(7) Uani 1 1 d . . .
H7 H 0.2862 -0.2868 0.9065 0.068 Uiso 1 1 calc R . .
C8 C 0.2588(2) -0.20012(11) 0.8665(3) 0.0495(6) Uani 1 1 d . . .
H8 H 0.2001 -0.2034 0.7741 0.059 Uiso 1 1 calc R . .
C8A C 0.29767(19) -0.14530(10) 0.9296(3) 0.0379(5) Uani 1 1 d . . .
N9 N 0.25756(18) -0.08898(8) 0.8787(2) 0.0399(5) Uani 1 1 d . . .
C9A C 0.31684(18) -0.04757(9) 0.9816(2) 0.0328(5) Uani 1 1 d . . .
N1' N 0.08575(16) 0.07524(8) 0.63695(19) 0.0395(5) Uani 1 1 d . . .
C2' C 0.1860(2) 0.04268(10) 0.7120(3) 0.0394(5) Uani 1 1 d . . .
H2' H 0.2337 0.0236 0.6636 0.047 Uiso 1 1 calc R . .
C3' C 0.20285(19) 0.04308(9) 0.8636(2) 0.0361(5) Uani 1 1 d . . .
C3A' C 0.11024(19) 0.07791(10) 0.8903(2) 0.0360(5) Uani 1 1 d . . .
C4' C 0.0804(2) 0.09128(12) 1.0224(3) 0.0486(6) Uani 1 1 d . . .
H4' H 0.1238 0.0764 1.1169 0.058 Uiso 1 1 calc R . .
C5' C -0.0144(2) 0.12693(13) 1.0104(3) 0.0587(7) Uani 1 1 d . . .
H5' H -0.0351 0.1361 1.0977 0.070 Uiso 1 1 calc R . .
C6' C -0.0801(2) 0.14951(12) 0.8694(3) 0.0546(7) Uani 1 1 d . . .
H6' H -0.1430 0.1740 0.8647 0.066 Uiso 1 1 calc R . .
C7' C -0.05366(19) 0.13629(11) 0.7370(3) 0.0438(6) Uani 1 1 d . . .
H7' H -0.0974 0.1515 0.6429 0.053 Uiso 1 1 calc R . .
C7A' C 0.04069(18) 0.09945(10) 0.7492(2) 0.0351(5) Uani 1 1 d . . .
S S 0.05740(5) 0.09527(3) 0.45606(6) 0.04076(17) Uani 1 1 d . . .
O1A O -0.06083(14) 0.11494(8) 0.40827(18) 0.0518(5) Uani 1 1 d . . .
O1B O 0.09244(16) 0.04682(8) 0.38079(18) 0.0556(5) Uani 1 1 d . . .
C12 C 0.1491(2) 0.15578(11) 0.4577(3) 0.0431(6) Uani 1 1 d . . .
C13 C 0.2567(3) 0.14496(13) 0.4403(4) 0.0645(8) Uani 1 1 d . . .
H13 H 0.2794 0.1065 0.4256 0.077 Uiso 1 1 calc R . .
C14 C 0.3304(3) 0.19212(16) 0.4449(4) 0.0844(10) Uani 1 1 d . . .
H14 H 0.4033 0.1854 0.4331 0.101 Uiso 1 1 calc R . .
C15 C 0.2974(3) 0.24861(15) 0.4667(4) 0.0824(10) Uani 1 1 d . . .
H15 H 0.3472 0.2802 0.4681 0.099 Uiso 1 1 calc R . .
C16 C 0.1921(3) 0.25841(14) 0.4860(5) 0.0944(12) Uani 1 1 d . . .
H16 H 0.1705 0.2968 0.5028 0.113 Uiso 1 1 calc R . .
C17 C 0.1159(3) 0.21177(13) 0.4813(4) 0.0734(9) Uani 1 1 d . . .
H17 H 0.0433 0.2187 0.4941 0.088 Uiso 1 1 calc R . .
H9 H 0.201(2) -0.0835(11) 0.802(3) 0.047(7) Uiso 1 1 d . . .

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
C1 0.0365(12) 0.0348(12) 0.0321(12) 0.0038(10) 0.0084(9) 0.0031(10)
C2 0.0416(13) 0.0298(12) 0.0433(13) 0.0024(10) 0.0129(10) 0.0028(10)
O2 0.0579(12) 0.0295(9) 0.0674(13) -0.0014(8) -0.0005(9) 0.0040(8)
C3 0.0338(12) 0.0342(12) 0.0413(13) -0.0022(10) 0.0084(10) 0.0001(10)
C10 0.0372(13) 0.0421(14) 0.0472(14) -0.0079(12) 0.0084(11) -0.0019(11)
O4 0.0401(9) 0.0476(10) 0.0504(10) -0.0146(8) -0.0019(8) -0.0014(8)
O3 0.0650(13) 0.0399(11) 0.0826(15) -0.0175(10) -0.0059(10) -0.0009(9)
C11 0.0448(15) 0.0710(19) 0.0588(17) -0.0277(15) 0.0010(13) -0.0077(13)
C4 0.0316(12) 0.0363(12) 0.0371(12) 0.0027(10) 0.0036(9) 0.0038(10)
C4A 0.0337(12) 0.0312(12) 0.0368(12) 0.0006(10) 0.0099(10) 0.0022(9)
C4B 0.0346(12) 0.0342(12) 0.0425(13) -0.0014(10) 0.0117(10) 0.0025(10)
C5 0.0444(14) 0.0377(14) 0.0558(16) 0.0047(12) 0.0086(12) 0.0063(11)
C6 0.0574(17) 0.0338(14) 0.076(2) 0.0059(13) 0.0215(15) 0.0101(12)
C7 0.0600(17) 0.0348(14) 0.077(2) -0.0135(14) 0.0217(15) -0.0060(13)
C8 0.0489(15) 0.0420(14) 0.0544(16) -0.0120(12) 0.0106(12) -0.0048(12)
C8A 0.0390(13) 0.0346(12) 0.0404(13) -0.0019(10) 0.0124(10) 0.0019(10)
N9 0.0406(11) 0.0386(11) 0.0338(11) -0.0028(9) 0.0010(9) 0.0014(9)
C9A 0.0329(11) 0.0354(12) 0.0291(11) 0.0009(10) 0.0076(9) 0.0015(9)
N1' 0.0453(11) 0.0432(11) 0.0274(10) 0.0052(8) 0.0073(8) 0.0091(9)
C2' 0.0446(13) 0.0362(12) 0.0376(13) 0.0027(10) 0.0126(10) 0.0100(10)
C3' 0.0405(13) 0.0312(12) 0.0340(12) 0.0037(10) 0.0075(10) 0.0012(10)
C3A' 0.0351(12) 0.0398(13) 0.0320(11) 0.0036(10) 0.0083(9) -0.0009(10)
C4' 0.0473(15) 0.0648(17) 0.0337(13) 0.0076(12) 0.0122(11) 0.0053(13)
C5' 0.0501(16) 0.087(2) 0.0440(15) 0.0018(14) 0.0224(12) 0.0107(15)
C6' 0.0390(14) 0.0734(19) 0.0515(16) -0.0009(14) 0.0139(12) 0.0129(13)
C7' 0.0351(13) 0.0530(15) 0.0389(13) 0.0046(11) 0.0046(10) 0.0052(11)
C7A' 0.0368(12) 0.0370(12) 0.0312(11) 0.0014(10) 0.0095(9) -0.0007(10)
S 0.0456(4) 0.0457(3) 0.0266(3) 0.0023(3) 0.0041(2) 0.0011(3)
O1A 0.0403(9) 0.0706(12) 0.0361(9) 0.0067(8) -0.0011(7) 0.0003(8)
O1B 0.0781(13) 0.0523(11) 0.0354(9) -0.0065(8) 0.0155(9) 0.0009(9)
C12 0.0462(14) 0.0460(14) 0.0361(13) 0.0036(11) 0.0107(11) 0.0020(11)
C13 0.0574(18) 0.0620(18) 0.078(2) -0.0140(16) 0.0262(15) -0.0035(15)
C14 0.067(2) 0.089(3) 0.108(3) -0.025(2) 0.043(2) -0.0212(19)
C15 0.082(2) 0.068(2) 0.106(3) -0.005(2) 0.040(2) -0.0226(19)
C16 0.100(3) 0.0443(18) 0.152(4) -0.003(2) 0.058(3) -0.0028(18)
C17 0.068(2) 0.0487(17) 0.114(3) 0.0085(17) 0.0436(19) 0.0071(15)

_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 C9A 1.395(3) . ?
C1 C2 1.397(3) . ?
C1 C3' 1.479(3) . ?
C2 O2 1.353(3) . ?
C2 C3 1.417(3) . ?
O2 H2 0.8200 . ?
C3 C4 1.396(3) . ?
C3 C10 1.460(3) . ?
C10 O3 1.225(3) . ?
C10 O4 1.329(3) . ?
O4 C11 1.451(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C4 C4A 1.376(3) . ?
C4 H4 0.9300 . ?
C4A C9A 1.415(3) . ?
C4A C4B 1.445(3) . ?
C4B C5 1.390(3) . ?
C4B C8A 1.407(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(4) . ?
C7 H7 0.9300 . ?
C8 C8A 1.385(3) . ?
C8 H8 0.9300 . ?
C8A N9 1.389(3) . ?
N9 C9A 1.367(3) . ?
N9 H9 0.83(2) . ?
N1' C2' 1.405(3) . ?
N1' C7A' 1.409(3) . ?
N1' S 1.6515(18) . ?
C2' C3' 1.342(3) . ?
C2' H2' 0.9300 . ?
C3' C3A' 1.445(3) . ?
C3A' C4' 1.395(3) . ?
C3A' C7A' 1.400(3) . ?
C4' C5' 1.375(4) . ?
C4' H4' 0.9300 . ?
C5' C6' 1.393(4) . ?
C5' H5' 0.9300 . ?
C6' C7' 1.376(3) . ?
C6' H6' 0.9300 . ?
C7' C7A' 1.386(3) . ?
C7' H7' 0.9300 . ?
S O1B 1.4219(18) . ?
S O1A 1.4309(17) . ?
S C12 1.754(2) . ?
C12 C17 1.361(4) . ?
C12 C13 1.376(4) . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.352(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(4) . ?
C16 H16 0.9300 . ?
C17 H17 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
C9A C1 C2 116.38(19) . . ?
C9A C1 C3' 122.41(19) . . ?
C2 C1 C3' 121.20(19) . . ?
O2 C2 C1 116.52(19) . . ?
O2 C2 C3 121.6(2) . . ?
C1 C2 C3 121.9(2) . . ?
C2 O2 H2 109.5 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 C10 121.5(2) . . ?
C2 C3 C10 119.0(2) . . ?
O3 C10 O4 121.2(2) . . ?
O3 C10 C3 124.2(2) . . ?
O4 C10 C3 114.6(2) . . ?
C10 O4 C11 116.44(19) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4A C4 C3 120.2(2) . . ?
C4A C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C4A C9A 119.12(19) . . ?
C4 C4A C4B 134.2(2) . . ?
C9A C4A C4B 106.60(19) . . ?
C5 C4B C8A 119.1(2) . . ?
C5 C4B C4A 134.2(2) . . ?
C8A C4B C4A 106.58(19) . . ?
C6 C5 C4B 118.9(2) . . ?
C6 C5 H5 120.6 . . ?
C4B C5 H5 120.6 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 122.0(2) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C8A 117.2(2) . . ?
C7 C8 H8 121.4 . . ?
C8A C8 H8 121.4 . . ?
C8 C8A N9 129.5(2) . . ?
C8 C8A C4B 122.1(2) . . ?
N9 C8A C4B 108.44(19) . . ?
C9A N9 C8A 109.61(19) . . ?
C9A N9 H9 127.7(17) . . ?
C8A N9 H9 122.4(17) . . ?
N9 C9A C1 128.5(2) . . ?
N9 C9A C4A 108.65(18) . . ?
C1 C9A C4A 122.86(19) . . ?
C2' N1' C7A' 108.00(17) . . ?
C2' N1' S 121.50(15) . . ?
C7A' N1' S 128.11(15) . . ?
C3' C2' N1' 110.09(19) . . ?
C3' C2' H2' 125.0 . . ?
N1' C2' H2' 125.0 . . ?
C2' C3' C3A' 107.13(19) . . ?
C2' C3' C1 126.5(2) . . ?
C3A' C3' C1 126.36(19) . . ?
C4' C3A' C7A' 119.1(2) . . ?
C4' C3A' C3' 132.7(2) . . ?
C7A' C3A' C3' 108.14(19) . . ?
C5' C4' C3A' 118.8(2) . . ?
C5' C4' H4' 120.6 . . ?
C3A' C4' H4' 120.6 . . ?
C4' C5' C6' 121.1(2) . . ?
C4' C5' H5' 119.5 . . ?
C6' C5' H5' 119.5 . . ?
C7' C6' C5' 121.4(2) . . ?
C7' C6' H6' 119.3 . . ?
C5' C6' H6' 119.3 . . ?
C6' C7' C7A' 117.4(2) . . ?
C6' C7' H7' 121.3 . . ?
C7A' C7' H7' 121.3 . . ?
C7' C7A' C3A' 122.2(2) . . ?
C7' C7A' N1' 131.3(2) . . ?
C3A' C7A' N1' 106.50(18) . . ?
O1B S O1A 120.23(11) . . ?
O1B S N1' 105.92(10) . . ?
O1A S N1' 106.21(10) . . ?
O1B S C12 108.85(11) . . ?
O1A S C12 109.26(11) . . ?
N1' S C12 105.31(11) . . ?
C17 C12 C13 121.1(3) . . ?
C17 C12 S 120.5(2) . . ?
C13 C12 S 118.4(2) . . ?
C12 C13 C14 118.8(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 118.9(3) . . ?
C12 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 C2 O2 178.0(2) . . . . ?
C3' C1 C2 O2 -2.8(3) . . . . ?
C9A C1 C2 C3 -1.3(3) . . . . ?
C3' C1 C2 C3 177.9(2) . . . . ?
O2 C2 C3 C4 -180.0(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
O2 C2 C3 C10 0.5(3) . . . . ?
C1 C2 C3 C10 179.8(2) . . . . ?
C4 C3 C10 O3 -179.7(2) . . . . ?
C2 C3 C10 O3 -0.2(4) . . . . ?
C4 C3 C10 O4 1.1(3) . . . . ?
C2 C3 C10 O4 -179.3(2) . . . . ?
O3 C10 O4 C11 -3.6(3) . . . . ?
C3 C10 O4 C11 175.6(2) . . . . ?
C2 C3 C4 C4A 0.9(3) . . . . ?
C10 C3 C4 C4A -179.6(2) . . . . ?
C3 C4 C4A C9A 1.0(3) . . . . ?
C3 C4 C4A C4B -176.4(2) . . . . ?
C4 C4A C4B C5 3.8(5) . . . . ?
C9A C4A C4B C5 -173.8(3) . . . . ?
C4 C4A C4B C8A 179.7(2) . . . . ?
C9A C4A C4B C8A 2.1(2) . . . . ?
C8A C4B C5 C6 0.1(3) . . . . ?
C4A C4B C5 C6 175.6(2) . . . . ?
C4B C5 C6 C7 1.7(4) . . . . ?
C5 C6 C7 C8 -1.8(4) . . . . ?
C6 C7 C8 C8A -0.1(4) . . . . ?
C7 C8 C8A N9 -176.4(2) . . . . ?
C7 C8 C8A C4B 2.0(4) . . . . ?
C5 C4B C8A C8 -2.0(3) . . . . ?
C4A C4B C8A C8 -178.6(2) . . . . ?
C5 C4B C8A N9 176.6(2) . . . . ?
C4A C4B C8A N9 0.0(2) . . . . ?
C8 C8A N9 C9A 176.3(2) . . . . ?
C4B C8A N9 C9A -2.3(3) . . . . ?
C8A N9 C9A C1 -174.6(2) . . . . ?
C8A N9 C9A C4A 3.6(3) . . . . ?
C2 C1 C9A N9 -178.8(2) . . . . ?
C3' C1 C9A N9 2.0(4) . . . . ?
C2 C1 C9A C4A 3.3(3) . . . . ?
C3' C1 C9A C4A -175.9(2) . . . . ?
C4 C4A C9A N9 178.49(19) . . . . ?
C4B C4A C9A N9 -3.5(2) . . . . ?
C4 C4A C9A C1 -3.2(3) . . . . ?
C4B C4A C9A C1 174.8(2) . . . . ?
C7A' N1' C2' C3' 2.7(3) . . . . ?
S N1' C2' C3' 166.50(16) . . . . ?
N1' C2' C3' C3A' -0.5(3) . . . . ?
N1' C2' C3' C1 179.5(2) . . . . ?
C9A C1 C3' C2' -59.1(3) . . . . ?
C2 C1 C3' C2' 121.8(3) . . . . ?
C9A C1 C3' C3A' 121.0(2) . . . . ?
C2 C1 C3' C3A' -58.2(3) . . . . ?
C2' C3' C3A' C4' 176.7(3) . . . . ?
C1 C3' C3A' C4' -3.3(4) . . . . ?
C2' C3' C3A' C7A' -1.9(3) . . . . ?
C1 C3' C3A' C7A' 178.1(2) . . . . ?
C7A' C3A' C4' C5' -2.1(4) . . . . ?
C3' C3A' C4' C5' 179.4(3) . . . . ?
C3A' C4' C5' C6' 0.0(4) . . . . ?
C4' C5' C6' C7' 1.0(4) . . . . ?
C5' C6' C7' C7A' 0.2(4) . . . . ?
C6' C7' C7A' C3A' -2.4(4) . . . . ?
C6' C7' C7A' N1' 176.0(2) . . . . ?
C4' C3A' C7A' C7' 3.4(3) . . . . ?
C3' C3A' C7A' C7' -177.8(2) . . . . ?
C4' C3A' C7A' N1' -175.3(2) . . . . ?
C3' C3A' C7A' N1' 3.5(2) . . . . ?
C2' N1' C7A' C7' 177.6(2) . . . . ?
S N1' C7A' C7' 15.2(4) . . . . ?
C2' N1' C7A' C3A' -3.8(2) . . . . ?
S N1' C7A' C3A' -166.17(17) . . . . ?
C2' N1' S O1B 38.2(2) . . . . ?
C7A' N1' S O1B -161.57(19) . . . . ?
C2' N1' S O1A 167.08(17) . . . . ?
C7A' N1' S O1A -32.6(2) . . . . ?
C2' N1' S C12 -77.1(2) . . . . ?
C7A' N1' S C12 83.2(2) . . . . ?
O1B S C12 C17 160.8(2) . . . . ?
O1A S C12 C17 27.7(3) . . . . ?
N1' S C12 C17 -86.0(2) . . . . ?
O1B S C12 C13 -21.6(2) . . . . ?
O1A S C12 C13 -154.7(2) . . . . ?
N1' S C12 C13 91.6(2) . . . . ?
C17 C12 C13 C14 -1.0(4) . . . . ?
S C12 C13 C14 -178.5(2) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 1.0(6) . . . . ?
C14 C15 C16 C17 -1.2(6) . . . . ?
C13 C12 C17 C16 0.7(5) . . . . ?
S C12 C17 C16 178.2(3) . . . . ?
C15 C16 C17 C12 0.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.048
_chemical_compound_source        synthesis