data_2007src0079
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. E. McDonald
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H13 N O5 S'
_chemical_formula_weight          295.30
 
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
 
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                    15.8005(6)
_cell_length_b                    5.17630(10)
_cell_length_c                    16.9786(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  99.723(2)
_cell_angle_gamma                 90.00
_cell_volume                      1368.70(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3349
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Needle
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.41
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.433
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              616
_exptl_absorpt_coefficient_mu     0.255
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9027
_exptl_absorpt_correction_T_max   0.9949
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details
;
SADABS was used to perform the Absorption correction
Parameter refinement on 12451 reflections reduced R(int) from 0.1094 to 0.0531
Ratio of minimum to maximum apparent transmission: 0.889747
The given Tmin and Tmax were generated using the SHELX SIZE command
;


_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             13652
_diffrn_reflns_av_R_equivalents   0.0522
_diffrn_reflns_av_sigmaI/netI     0.0480
_diffrn_reflns_limit_h_min        -20
_diffrn_reflns_limit_h_max        20
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.26
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3138
_reflns_number_gt                 2581
_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   'WinGX (Farrugia, 1999)'
 
_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)+(0.0050P)²+2.7074P] 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          3138
_refine_ls_number_parameters      182
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0722
_refine_ls_R_factor_gt            0.0566
_refine_ls_wR_factor_ref          0.1168
_refine_ls_wR_factor_gt           0.1070
_refine_ls_goodness_of_fit_ref    1.094
_refine_ls_restrained_S_all       1.094
_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 0.97137(16) -0.0932(5) 0.25600(15) 0.0207(5) Uani 1 1 d . . .
C2 C 0.98241(16) -0.0288(5) 0.17646(14) 0.0198(5) Uani 1 1 d . . .
C3 C 1.04277(16) -0.1385(5) 0.13991(15) 0.0207(5) Uani 1 1 d . . .
H3 H 1.0479 -0.0871 0.0872 0.025 Uiso 1 1 calc R . .
C4 C 1.16564(16) -0.3867(5) 0.13866(15) 0.0215(5) Uani 1 1 d . . .
H4A H 1.1459 -0.4022 0.0803 0.026 Uiso 1 1 calc R . .
H4B H 1.1888 -0.5562 0.1589 0.026 Uiso 1 1 calc R . .
C5 C 1.23510(16) -0.1846(5) 0.15489(14) 0.0202(5) Uani 1 1 d . . .
C6 C 1.37741(18) -0.0875(6) 0.13434(17) 0.0295(6) Uani 1 1 d . . .
H6A H 1.4139 -0.1056 0.1875 0.035 Uiso 1 1 calc R . .
H6B H 1.3572 0.0936 0.1279 0.035 Uiso 1 1 calc R . .
C7 C 1.42751(18) -0.1574(6) 0.06956(17) 0.0317(6) Uani 1 1 d . . .
H7A H 1.4459 -0.3381 0.0758 0.047 Uiso 1 1 calc R . .
H7B H 1.4781 -0.0455 0.0734 0.047 Uiso 1 1 calc R . .
H7C H 1.3912 -0.1341 0.0173 0.047 Uiso 1 1 calc R . .
C8 C 0.81373(16) 0.0119(5) 0.10469(14) 0.0200(5) Uani 1 1 d . . .
C9 C 0.75279(17) 0.0385(5) 0.15434(14) 0.0223(5) Uani 1 1 d . . .
H9 H 0.7600 0.1642 0.1957 0.027 Uiso 1 1 calc R . .
C10 C 0.68139(17) -0.1210(5) 0.14263(15) 0.0259(6) Uani 1 1 d . . .
H10 H 0.6393 -0.1057 0.1762 0.031 Uiso 1 1 calc R . .
C11 C 0.67132(17) -0.3032(5) 0.08182(15) 0.0252(5) Uani 1 1 d . . .
H11 H 0.6229 -0.4146 0.0747 0.030 Uiso 1 1 calc R . .
C12 C 0.73159(17) -0.3237(5) 0.03130(15) 0.0260(6) Uani 1 1 d . . .
H12 H 0.7234 -0.4458 -0.0111 0.031 Uiso 1 1 calc R . .
C13 C 0.80360(16) -0.1667(5) 0.04261(15) 0.0226(5) Uani 1 1 d . . .
H13 H 0.8453 -0.1808 0.0086 0.027 Uiso 1 1 calc R . .
N1 N 0.96202(16) -0.1415(5) 0.31965(13) 0.0295(5) Uani 1 1 d . . .
O1 O 1.09497(11) -0.3175(3) 0.17687(10) 0.0229(4) Uani 1 1 d . . .
O2 O 1.22666(12) 0.0215(4) 0.18610(11) 0.0278(4) Uani 1 1 d . . .
O3 O 1.30402(12) -0.2642(4) 0.12732(11) 0.0263(4) Uani 1 1 d . . .
O4 O 0.89815(12) 0.3994(3) 0.17765(10) 0.0248(4) Uani 1 1 d . . .
O5 O 0.93863(12) 0.2464(4) 0.04993(10) 0.0257(4) Uani 1 1 d . . .
S1 S 0.90927(4) 0.19205(12) 0.12425(3) 0.01951(15) 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 N1 1.143(3) . ?
C1 C2 1.430(3) . ?
C2 C3 1.348(3) . ?
C2 S1 1.756(3) . ?
C3 O1 1.326(3) . ?
C3 H3 0.9500 . ?
C4 O1 1.428(3) . ?
C4 C5 1.507(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O2 1.208(3) . ?
C5 O3 1.322(3) . ?
C6 O3 1.466(3) . ?
C6 C7 1.504(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.391(3) . ?
C8 C9 1.390(3) . ?
C8 S1 1.758(3) . ?
C9 C10 1.385(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O4 S1 1.4349(18) . ?
O5 S1 1.4438(17) . ?
 
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 C2 179.0(3) . . ?
C3 C2 C1 123.0(2) . . ?
C3 C2 S1 119.89(19) . . ?
C1 C2 S1 116.99(18) . . ?
O1 C3 C2 120.6(2) . . ?
O1 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O1 C4 C5 110.1(2) . . ?
O1 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
O1 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?
O2 C5 O3 126.1(2) . . ?
O2 C5 C4 124.2(2) . . ?
O3 C5 C4 109.7(2) . . ?
O3 C6 C7 107.3(2) . . ?
O3 C6 H6A 110.3 . . ?
C7 C6 H6A 110.3 . . ?
O3 C6 H6B 110.3 . . ?
C7 C6 H6B 110.3 . . ?
H6A C6 H6B 108.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 121.5(2) . . ?
C13 C8 S1 118.76(19) . . ?
C9 C8 S1 119.59(19) . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 118.8(2) . . ?
C12 C13 H13 120.6 . . ?
C8 C13 H13 120.6 . . ?
C3 O1 C4 115.58(19) . . ?
C5 O3 C6 117.7(2) . . ?
O4 S1 O5 119.88(11) . . ?
O4 S1 C2 107.96(11) . . ?
O5 S1 C2 106.67(11) . . ?
O4 S1 C8 108.87(12) . . ?
O5 S1 C8 109.32(11) . . ?
C2 S1 C8 102.77(12) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.341
_refine_diff_density_min   -0.398
_refine_diff_density_rms    0.071
