
#######################################################################
#
#                 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 
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# 
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#  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 
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data_ss75
_database_code_depnum_ccdc_archive 'CCDC 765775'
#TrackingRef 'ss75.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N3 O5 S'
_chemical_formula_weight         373.38

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'

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

_cell_length_a                   4.3449(2)
_cell_length_b                   18.7349(5)
_cell_length_c                   10.4511(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.293(3)
_cell_angle_gamma                90.00
_cell_volume                     849.33(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23270
_cell_measurement_theta_min      2.1685
_cell_measurement_theta_max      31.4909

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            53082
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         30.03
_reflns_number_total             4948
_reflns_number_gt                4427
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

The molecule is achiral and crystallizes by chance in a chiral space group.
;

_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)+(0.0386P)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    'NH free, rigid methyl, others riding'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration .
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_number_reflns         4948
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.001
_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
S S 0.70307(7) 0.201062(17) 0.47240(3) 0.02458(7) Uani 1 1 d . . .
N1 N 0.6275(2) 0.31422(5) 0.31499(10) 0.0188(2) Uani 1 1 d . . .
H01 H 0.547(4) 0.3580(9) 0.3133(16) 0.032(4) Uiso 1 1 d . . .
N2 N 0.3808(2) 0.31795(5) 0.50472(10) 0.0184(2) Uani 1 1 d . . .
H02 H 0.352(3) 0.2975(8) 0.5696(14) 0.015(3) Uiso 1 1 d . . .
N3 N -0.4084(2) 0.50756(6) 0.88833(10) 0.0217(2) Uani 1 1 d . . .
O1 O 0.3184(2) 0.42349(5) 0.39621(8) 0.0249(2) Uani 1 1 d . . .
O2 O 1.3592(2) 0.26139(5) -0.19535(8) 0.02300(19) Uani 1 1 d . . .
O3 O 1.1666(2) 0.15317(4) -0.15384(8) 0.02212(19) Uani 1 1 d . . .
O4 O -0.4171(2) 0.57270(5) 0.89538(10) 0.0325(2) Uani 1 1 d . . .
O5 O -0.5401(2) 0.46760(5) 0.95986(10) 0.0340(2) Uani 1 1 d . . .
C1 C 0.5683(3) 0.27990(6) 0.42321(11) 0.0176(2) Uani 1 1 d . . .
C2 C 0.2705(3) 0.38658(6) 0.48935(11) 0.0179(2) Uani 1 1 d . . .
C11 C 0.7830(3) 0.28820(6) 0.20878(11) 0.0174(2) Uani 1 1 d . . .
C12 C 0.7506(3) 0.21775(6) 0.16702(11) 0.0203(2) Uani 1 1 d . . .
H12 H 0.6334 0.1847 0.2130 0.024 Uiso 1 1 calc R . .
C13 C 0.8915(3) 0.19654(7) 0.05758(10) 0.0190(2) Uani 1 1 d . . .
H13 H 0.8700 0.1487 0.0285 0.023 Uiso 1 1 calc R . .
C14 C 1.0643(3) 0.24457(6) -0.01022(11) 0.0173(2) Uani 1 1 d . . .
C15 C 1.0941(3) 0.31480(6) 0.03167(11) 0.0187(2) Uani 1 1 d . . .
H15 H 1.2116 0.3477 -0.0145 0.022 Uiso 1 1 calc R . .
C16 C 0.9529(3) 0.33707(6) 0.14069(11) 0.0197(2) Uani 1 1 d . . .
H16 H 0.9717 0.3852 0.1687 0.024 Uiso 1 1 calc R . .
C17 C 1.2141(3) 0.22209(6) -0.12857(11) 0.0179(2) Uani 1 1 d . . .
C18 C 1.3081(3) 0.12471(7) -0.26520(12) 0.0233(3) Uani 1 1 d . . .
H18A H 1.5338 0.1325 -0.2580 0.028 Uiso 1 1 calc R . .
H18B H 1.2228 0.1484 -0.3441 0.028 Uiso 1 1 calc R . .
C19 C 1.2367(3) 0.04603(7) -0.26943(14) 0.0324(3) Uani 1 1 d . . .
H19A H 1.3278 0.0230 -0.1920 0.049 Uiso 1 1 calc R . .
H19B H 1.3232 0.0248 -0.3452 0.049 Uiso 1 1 calc R . .
H19C H 1.0128 0.0391 -0.2739 0.049 Uiso 1 1 calc R . .
C21 C 0.0900(3) 0.41549(6) 0.59554(11) 0.0174(2) Uani 1 1 d . . .
C22 C 0.0783(3) 0.48991(6) 0.60784(11) 0.0197(2) Uani 1 1 d . . .
H22 H 0.1814 0.5193 0.5499 0.024 Uiso 1 1 calc R . .
C23 C -0.0840(3) 0.52089(6) 0.70466(12) 0.0202(2) Uani 1 1 d . . .
H23 H -0.0933 0.5712 0.7144 0.024 Uiso 1 1 calc R . .
C24 C -0.2310(3) 0.47571(6) 0.78612(11) 0.0180(2) Uani 1 1 d . . .
C25 C -0.2291(3) 0.40225(6) 0.77541(11) 0.0183(2) Uani 1 1 d . . .
H25 H -0.3369 0.3732 0.8325 0.022 Uiso 1 1 calc R . .
C26 C -0.0649(3) 0.37195(6) 0.67885(11) 0.0181(2) Uani 1 1 d . . .
H26 H -0.0583 0.3215 0.6696 0.022 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C1 1.6595(12) . ?
N1 C1 1.3388(15) . ?
N1 C11 1.4186(15) . ?
N2 C2 1.3782(15) . ?
N2 C1 1.4062(14) . ?
N3 O5 1.2230(14) . ?
N3 O4 1.2233(13) . ?
N3 C24 1.4785(15) . ?
O1 C2 1.2216(14) . ?
O2 C17 1.2155(14) . ?
O3 C17 1.3317(14) . ?
O3 C18 1.4488(14) . ?
C2 C21 1.4967(15) . ?
C11 C12 1.3948(17) . ?
C11 C16 1.3963(16) . ?
C12 C13 1.3861(16) . ?
C13 C14 1.3913(16) . ?
C14 C15 1.3904(16) . ?
C14 C17 1.4913(16) . ?
C15 C16 1.3889(16) . ?
C18 C19 1.5065(19) . ?
C21 C26 1.3942(16) . ?
C21 C22 1.4014(15) . ?
C22 C23 1.3928(17) . ?
C23 C24 1.3827(17) . ?
C24 C25 1.3808(16) . ?
C25 C26 1.3901(16) . ?

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
C1 N1 C11 128.26(10) . . ?
C2 N2 C1 127.74(10) . . ?
O5 N3 O4 123.84(11) . . ?
O5 N3 C24 118.43(10) . . ?
O4 N3 C24 117.73(10) . . ?
C17 O3 C18 116.62(10) . . ?
N1 C1 N2 114.47(10) . . ?
N1 C1 S 127.44(9) . . ?
N2 C1 S 118.03(9) . . ?
O1 C2 N2 123.16(11) . . ?
O1 C2 C21 120.42(10) . . ?
N2 C2 C21 116.41(10) . . ?
C12 C11 C16 120.52(11) . . ?
C12 C11 N1 121.74(11) . . ?
C16 C11 N1 117.58(10) . . ?
C13 C12 C11 119.21(11) . . ?
C12 C13 C14 120.77(12) . . ?
C15 C14 C13 119.66(11) . . ?
C15 C14 C17 119.42(10) . . ?
C13 C14 C17 120.91(10) . . ?
C16 C15 C14 120.33(11) . . ?
C15 C16 C11 119.50(11) . . ?
O2 C17 O3 123.59(11) . . ?
O2 C17 C14 124.80(11) . . ?
O3 C17 C14 111.61(10) . . ?
O3 C18 C19 106.71(10) . . ?
C26 C21 C22 120.22(11) . . ?
C26 C21 C2 122.93(10) . . ?
C22 C21 C2 116.85(10) . . ?
C23 C22 C21 120.25(11) . . ?
C24 C23 C22 117.61(11) . . ?
C25 C24 C23 123.71(11) . . ?
C25 C24 N3 117.83(10) . . ?
C23 C24 N3 118.44(10) . . ?
C24 C25 C26 118.14(11) . . ?
C25 C26 C21 120.05(11) . . ?

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
C11 N1 C1 N2 -173.62(11) . . . . ?
C11 N1 C1 S 9.38(19) . . . . ?
C2 N2 C1 N1 -4.33(17) . . . . ?
C2 N2 C1 S 172.98(10) . . . . ?
C1 N2 C2 O1 2.3(2) . . . . ?
C1 N2 C2 C21 -176.47(11) . . . . ?
C1 N1 C11 C12 36.52(18) . . . . ?
C1 N1 C11 C16 -148.20(12) . . . . ?
C16 C11 C12 C13 0.58(18) . . . . ?
N1 C11 C12 C13 175.72(11) . . . . ?
C11 C12 C13 C14 0.15(17) . . . . ?
C12 C13 C14 C15 -0.48(17) . . . . ?
C12 C13 C14 C17 -179.51(11) . . . . ?
C13 C14 C15 C16 0.09(17) . . . . ?
C17 C14 C15 C16 179.13(11) . . . . ?
C14 C15 C16 C11 0.62(18) . . . . ?
C12 C11 C16 C15 -0.96(18) . . . . ?
N1 C11 C16 C15 -176.30(11) . . . . ?
C18 O3 C17 O2 2.24(17) . . . . ?
C18 O3 C17 C14 -178.52(10) . . . . ?
C15 C14 C17 O2 -1.71(18) . . . . ?
C13 C14 C17 O2 177.32(12) . . . . ?
C15 C14 C17 O3 179.07(11) . . . . ?
C13 C14 C17 O3 -1.91(15) . . . . ?
C17 O3 C18 C19 176.98(11) . . . . ?
O1 C2 C21 C26 156.54(12) . . . . ?
N2 C2 C21 C26 -24.66(17) . . . . ?
O1 C2 C21 C22 -22.65(17) . . . . ?
N2 C2 C21 C22 156.14(11) . . . . ?
C26 C21 C22 C23 1.06(19) . . . . ?
C2 C21 C22 C23 -179.72(11) . . . . ?
C21 C22 C23 C24 -0.25(18) . . . . ?
C22 C23 C24 C25 -0.96(19) . . . . ?
C22 C23 C24 N3 -179.10(10) . . . . ?
O5 N3 C24 C25 1.30(16) . . . . ?
O4 N3 C24 C25 -177.99(12) . . . . ?
O5 N3 C24 C23 179.54(12) . . . . ?
O4 N3 C24 C23 0.26(16) . . . . ?
C23 C24 C25 C26 1.32(19) . . . . ?
N3 C24 C25 C26 179.47(10) . . . . ?
C24 C25 C26 C21 -0.45(17) . . . . ?
C22 C21 C26 C25 -0.70(18) . . . . ?
C2 C21 C26 C25 -179.87(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H01 O1 0.892(16) 1.827(16) 2.6164(13) 146.2(15) .
N2 H02 O2 0.795(15) 2.546(15) 3.3154(14) 163.2(13) 1_456
C26 H26 N2 0.95 2.90 3.1036(16) 93.1 1_455
C19 H19B O1 0.98 2.53 3.3251(16) 138.1 2_745
C25 H25 O2 0.95 2.48 3.2126(15) 133.4 1_356
C26 H26 O2 0.95 2.50 3.0227(15) 114.6 1_456
C12 H12 O4 0.95 2.54 3.1308(15) 120.6 2_546
C13 H13 O4 0.95 2.59 3.1609(16) 118.9 2_546
C15 H15 O5 0.95 2.51 3.3795(15) 151.8 1_754

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.038
# end of cif file



