data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. N. Blagden
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C17 H25 N3 O8 S2'
_chemical_formula_weight          463.52
_chemical_absolute_configuration   unk
 
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            orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
_symmetry_space_group_name_hall   'P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    9.1633(5)
_cell_length_b                    27.6017(15)
_cell_length_c                    8.0214(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2028.79(19)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2555
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        slab
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.42
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.07
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.518
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              976
_exptl_absorpt_coefficient_mu     0.314
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8793
_exptl_absorpt_correction_T_max   0.9783
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)'

_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             14775
_diffrn_reflns_av_R_equivalents   0.0427
_diffrn_reflns_av_sigmaI/netI     0.0449
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -35
_diffrn_reflns_limit_k_max        35
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          3.14
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4583
_reflns_number_gt                 4243
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0348P)²+1.3890P] where P=(Fo²+2Fc²)/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    -0.05(7)
_refine_ls_number_reflns          4583
_refine_ls_number_parameters      300
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0453
_refine_ls_R_factor_gt            0.0399
_refine_ls_wR_factor_ref          0.0959
_refine_ls_wR_factor_gt           0.0929
_refine_ls_goodness_of_fit_ref    1.083
_refine_ls_restrained_S_all       1.083
_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
C1 C 0.2364(3) 0.92732(10) 0.2896(4) 0.0257(5) Uani 1 1 d . . .
H1 H 0.3028 0.9560 0.2964 0.031 Uiso 1 1 calc R . .
C2 C 0.0781(3) 0.94377(9) 0.2718(4) 0.0240(6) Uani 1 1 d . . .
H2 H 0.0143 0.9147 0.2571 0.029 Uiso 1 1 calc R . .
C3 C 0.0301(3) 0.97124(9) 0.4257(4) 0.0233(5) Uani 1 1 d . . .
H3 H 0.0855 1.0024 0.4342 0.028 Uiso 1 1 calc R . .
C4 C 0.0577(3) 0.94042(9) 0.5807(3) 0.0219(5) Uani 1 1 d . . .
H4 H -0.0068 0.9112 0.5756 0.026 Uiso 1 1 calc R . .
C5 C 0.2156(3) 0.92355(10) 0.5859(3) 0.0239(5) Uani 1 1 d . . .
H5 H 0.2816 0.9522 0.5978 0.029 Uiso 1 1 calc R . .
C6 C 0.2439(3) 0.88831(9) 0.7260(3) 0.0235(5) Uani 1 1 d . . .
H6A H 0.3458 0.8766 0.7193 0.028 Uiso 1 1 calc R . .
H6B H 0.2313 0.9050 0.8342 0.028 Uiso 1 1 calc R . .
C7 C 0.4210(3) 0.88142(10) 0.1349(3) 0.0222(5) Uani 1 1 d . . .
C8 C 0.5383(3) 0.91169(9) 0.1728(4) 0.0252(6) Uani 1 1 d . . .
H8 H 0.5206 0.9432 0.2159 0.030 Uiso 1 1 calc R . .
C9 C 0.6813(3) 0.89607(9) 0.1478(3) 0.0240(6) Uani 1 1 d . . .
H9 H 0.7607 0.9169 0.1732 0.029 Uiso 1 1 calc R . .
C10 C 0.7072(3) 0.84995(9) 0.0858(3) 0.0191(5) Uani 1 1 d . . .
C11 C 0.5898(3) 0.81973(9) 0.0456(3) 0.0230(5) Uani 1 1 d . . .
H11 H 0.6072 0.7883 0.0017 0.028 Uiso 1 1 calc R . .
C12 C 0.4486(3) 0.83561(9) 0.0699(3) 0.0237(5) Uani 1 1 d . . .
H12 H 0.3693 0.8150 0.0418 0.028 Uiso 1 1 calc R . .
C13 C 0.9337(3) 0.79088(9) 0.3370(3) 0.0189(5) Uani 1 1 d . . .
C14 C 0.8612(3) 0.71904(9) 0.5033(3) 0.0255(6) Uani 1 1 d . . .
H14 H 0.8226 0.6900 0.5488 0.031 Uiso 1 1 calc R . .
C15 C 0.9437(3) 0.75033(9) 0.5867(3) 0.0244(5) Uani 1 1 d . . .
H15 H 0.9726 0.7456 0.6993 0.029 Uiso 1 1 calc R . .
N1 N 0.2764(3) 0.89723(9) 0.1528(3) 0.0247(5) Uani 1 1 d . . .
N2 N 0.9627(2) 0.82773(7) 0.2371(3) 0.0196(4) Uani 1 1 d . . .
N3 N 0.9831(2) 0.79019(8) 0.4941(3) 0.0213(5) Uani 1 1 d . . .
O1 O 0.2502(2) 0.89814(6) 0.4365(2) 0.0259(4) Uani 1 1 d . . .
O2 O 0.0610(2) 0.97517(7) 0.1304(3) 0.0290(4) Uani 1 1 d . . .
O3 O -0.1230(2) 0.98104(7) 0.4194(3) 0.0283(4) Uani 1 1 d . . .
O4 O 0.0284(2) 0.96574(7) 0.7322(3) 0.0279(4) Uani 1 1 d . . .
O5 O 0.1463(2) 0.84787(6) 0.7175(2) 0.0232(4) Uani 1 1 d . . .
O6 O 0.9643(2) 0.86921(6) -0.0274(2) 0.0245(4) Uani 1 1 d . . .
O7 O 0.8845(2) 0.78424(6) -0.0266(2) 0.0237(4) Uani 1 1 d . . .
S1 S 0.88784(6) 0.83034(2) 0.05711(8) 0.01827(13) Uani 1 1 d . . .
S2 S 0.83337(7) 0.73854(2) 0.29943(8) 0.02258(15) Uani 1 1 d . . .
H1N H 0.212(4) 0.8718(13) 0.157(4) 0.042(10) Uiso 1 1 d . . .
H2O H 0.062(5) 0.9534(15) 0.021(6) 0.068(13) Uiso 1 1 d . . .
H3N H 1.034(3) 0.8107(12) 0.532(4) 0.028(9) Uiso 1 1 d . . .
H3O H -0.142(4) 1.0035(14) 0.335(5) 0.058(12) Uiso 1 1 d . . .
H4O H -0.079(5) 0.9614(17) 0.779(6) 0.084(15) Uiso 1 1 d . . .
H5O H 0.082(5) 0.8493(15) 0.808(5) 0.069(13) Uiso 1 1 d . . .
C21 C 0.6259(3) 0.91426(11) 0.6726(4) 0.0314(6) Uani 1 1 d . . .
H21A H 0.5489 0.9239 0.5926 0.038 Uiso 1 1 calc R . .
H21B H 0.5782 0.9073 0.7807 0.038 Uiso 1 1 calc R . .
C22 C 0.6993(3) 0.86878(11) 0.6101(4) 0.0321(7) Uani 1 1 d . . .
H22A H 0.7428 0.8750 0.5006 0.048 Uiso 1 1 calc R . .
H22B H 0.6269 0.8428 0.6006 0.048 Uiso 1 1 calc R . .
H22C H 0.7758 0.8590 0.6887 0.048 Uiso 1 1 calc R . .
O21 O 0.7255(2) 0.95378(7) 0.6937(3) 0.0300(4) Uani 1 1 d . . .
H21O H 0.740(5) 0.9632(15) 0.579(6) 0.068(13) Uiso 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 N1 1.425(4) . ?
C1 O1 1.432(3) . ?
C1 C2 1.527(4) . ?
C1 H1 1.0000 . ?
C2 O2 1.436(3) . ?
C2 C3 1.514(4) . ?
C2 H2 1.0000 . ?
C3 O3 1.429(3) . ?
C3 C4 1.528(4) . ?
C3 H3 1.0000 . ?
C4 O4 1.427(3) . ?
C4 C5 1.521(4) . ?
C4 H4 1.0000 . ?
C5 O1 1.425(3) . ?
C5 C6 1.508(4) . ?
C5 H5 1.0000 . ?
C6 O5 1.432(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.391(4) . ?
C7 C8 1.395(4) . ?
C7 N1 1.402(4) . ?
C8 C9 1.394(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(4) . ?
C10 S1 1.756(2) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N2 1.322(3) . ?
C13 N3 1.339(3) . ?
C13 S2 1.738(2) . ?
C14 C15 1.328(4) . ?
C14 S2 1.741(3) . ?
C14 H14 0.9500 . ?
C15 N3 1.376(3) . ?
C15 H15 0.9500 . ?
N1 H1N 0.92(4) . ?
N2 S1 1.600(2) . ?
N3 H3N 0.79(3) . ?
O2 H2O 1.06(5) . ?
O3 H3O 0.93(4) . ?
O4 H4O 1.06(5) . ?
O5 H5O 0.93(5) . ?
O6 S1 1.4498(18) . ?
O7 S1 1.4388(18) . ?
C21 O21 1.432(3) . ?
C21 C22 1.510(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O21 H21O 0.97(5) . ?
 
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
N1 C1 O1 106.5(2) . . ?
N1 C1 C2 110.2(2) . . ?
O1 C1 C2 109.1(2) . . ?
N1 C1 H1 110.3 . . ?
O1 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
O2 C2 C3 108.0(2) . . ?
O2 C2 C1 110.9(2) . . ?
C3 C2 C1 110.4(2) . . ?
O2 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
O3 C3 C2 110.6(2) . . ?
O3 C3 C4 107.3(2) . . ?
C2 C3 C4 109.6(2) . . ?
O3 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
O4 C4 C5 107.8(2) . . ?
O4 C4 C3 112.9(2) . . ?
C5 C4 C3 110.5(2) . . ?
O4 C4 H4 108.5 . . ?
C5 C4 H4 108.5 . . ?
C3 C4 H4 108.5 . . ?
O1 C5 C6 105.7(2) . . ?
O1 C5 C4 109.8(2) . . ?
C6 C5 C4 112.4(2) . . ?
O1 C5 H5 109.6 . . ?
C6 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
O5 C6 C5 111.1(2) . . ?
O5 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
O5 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C12 C7 C8 119.1(2) . . ?
C12 C7 N1 119.5(2) . . ?
C8 C7 N1 121.3(2) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 S1 119.41(19) . . ?
C11 C10 S1 120.74(19) . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
N2 C13 N3 120.9(2) . . ?
N2 C13 S2 129.9(2) . . ?
N3 C13 S2 109.27(19) . . ?
C15 C14 S2 110.8(2) . . ?
C15 C14 H14 124.6 . . ?
S2 C14 H14 124.6 . . ?
C14 C15 N3 113.4(3) . . ?
C14 C15 H15 123.3 . . ?
N3 C15 H15 123.3 . . ?
C7 N1 C1 120.2(2) . . ?
C7 N1 H1N 112(2) . . ?
C1 N1 H1N 104(2) . . ?
C13 N2 S1 119.67(18) . . ?
C13 N3 C15 115.5(2) . . ?
C13 N3 H3N 123(2) . . ?
C15 N3 H3N 121(2) . . ?
C5 O1 C1 113.31(18) . . ?
C2 O2 H2O 108(2) . . ?
C3 O3 H3O 109(3) . . ?
C4 O4 H4O 115(3) . . ?
C6 O5 H5O 109(3) . . ?
O7 S1 O6 116.53(11) . . ?
O7 S1 N2 112.97(11) . . ?
O6 S1 N2 104.35(11) . . ?
O7 S1 C10 108.25(12) . . ?
O6 S1 C10 106.78(11) . . ?
N2 S1 C10 107.46(12) . . ?
C13 S2 C14 90.96(13) . . ?
O21 C21 C22 112.9(2) . . ?
O21 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
O21 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 O21 H21O 100(3) . . ?
 
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
N3 H3N O5  0.79(3) 2.08(3) 2.826(3) 157(3) 1_655
O3 H3O O21  0.93(4) 1.81(4) 2.720(3) 165(4) 2_574
O4 H4O O21  1.06(5) 1.93(5) 2.812(3) 138(4) 1_455
O5 H5O O6  0.93(5) 1.80(5) 2.704(3) 165(4) 1_456
O21 H21O O3  0.97(5) 1.86(4) 2.708(3) 145(4) 1_655
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.458
_refine_diff_density_min   -0.294
_refine_diff_density_rms    0.058
