 
data_99ale005
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H9 N3 O2 S2'
_chemical_formula_weight          255.31
 
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    P21/c
 
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                    17.448(3)
_cell_length_b                    8.498(2)
_cell_length_c                    15.511(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  112.81(3)
_cell_angle_gamma                 90.00
_cell_volume                      2120.0(9)
_cell_formula_units_Z             8
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.15
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.600
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1056
_exptl_absorpt_coefficient_mu     0.489
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9085
_exptl_absorpt_correction_T_max   0.9302
_exptl_absorpt_process_details    
'SADABS V2.10 (Sheldrick, 2003)'

 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
__diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source                  
'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator    'graphite'
_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             17182
_diffrn_reflns_av_R_equivalents   0.1049
_diffrn_reflns_av_sigmaI/netI     0.0904
_diffrn_reflns_limit_h_min        -20
_diffrn_reflns_limit_h_max        20
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          2.53
_diffrn_reflns_theta_max          25.03
_reflns_number_total              3723
_reflns_number_gt                 2239
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_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)+(0.0463P)²+0.0000P] 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_number_reflns          3723
_refine_ls_number_parameters      361
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.1024
_refine_ls_R_factor_gt            0.0485
_refine_ls_wR_factor_ref          0.1072
_refine_ls_wR_factor_gt           0.0946
_refine_ls_goodness_of_fit_ref    0.930
_refine_ls_restrained_S_all       0.929
_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
S11 S 0.38389(6) 0.89999(10) 0.05813(5) 0.0224(2) Uani 1 1 d . . .
S12 S 0.35594(7) 0.67522(11) -0.12332(6) 0.0358(3) Uani 1 1 d . . .
O11 O 0.43201(15) 0.9805(3) 0.14457(14) 0.0265(6) Uani 1 1 d . . .
O12 O 0.37758(15) 0.9780(3) -0.02689(14) 0.0266(6) Uani 1 1 d . . .
N11 N 0.0429(2) 0.8058(3) 0.04887(19) 0.0229(7) Uani 1 1 d D . .
N12 N 0.42098(19) 0.7271(3) 0.06960(17) 0.0243(7) Uani 1 1 d . . .
N13 N 0.41198(18) 0.4768(3) 0.00738(18) 0.0226(7) Uani 1 1 d D . .
C11 C 0.1228(2) 0.8299(4) 0.0495(2) 0.0201(8) Uani 1 1 d . . .
C12 C 0.1921(2) 0.7666(4) 0.1219(2) 0.0217(9) Uani 1 1 d . . .
C13 C 0.2708(3) 0.7879(4) 0.1239(2) 0.0229(9) Uani 1 1 d . . .
C14 C 0.2825(2) 0.8755(4) 0.0544(2) 0.0202(8) Uani 1 1 d . . .
C15 C 0.2139(2) 0.9412(4) -0.0170(2) 0.0218(9) Uani 1 1 d . . .
C16 C 0.1357(2) 0.9194(4) -0.0190(2) 0.0195(8) Uani 1 1 d . . .
C17 C 0.3990(2) 0.6322(4) -0.0041(2) 0.0230(8) Uani 1 1 d . . .
C18 C 0.3886(3) 0.3902(5) -0.0737(2) 0.0296(9) Uani 1 1 d . . .
C19 C 0.3571(3) 0.4784(4) -0.1498(3) 0.0371(11) Uani 1 1 d . . .
S21 S 0.10697(6) 0.38054(10) 0.18198(5) 0.0227(2) Uani 1 1 d . . .
S22 S 0.13791(7) 0.14944(11) 0.36058(5) 0.0360(3) Uani 1 1 d . . .
O21 O 0.05793(15) 0.4621(3) 0.09711(14) 0.0283(6) Uani 1 1 d . . .
O22 O 0.11267(15) 0.4496(3) 0.26910(14) 0.0264(6) Uani 1 1 d . . .
N21 N 0.4468(2) 0.3251(4) 0.18213(19) 0.0249(7) Uani 1 1 d D . .
N22 N 0.07236(18) 0.2041(3) 0.16818(16) 0.0215(7) Uani 1 1 d . . .
N23 N 0.08016(19) -0.0471(3) 0.22929(17) 0.0228(7) Uani 1 1 d D . .
C21 C 0.3679(2) 0.3390(4) 0.1853(2) 0.0200(8) Uani 1 1 d . . .
C22 C 0.2995(3) 0.2777(4) 0.1113(2) 0.0241(9) Uani 1 1 d . . .
C23 C 0.2210(3) 0.2898(4) 0.1116(2) 0.0252(9) Uani 1 1 d . . .
C24 C 0.2085(2) 0.3648(4) 0.1857(2) 0.0202(8) Uani 1 1 d . . .
C25 C 0.2768(2) 0.4266(4) 0.2589(2) 0.0225(9) Uani 1 1 d . . .
C26 C 0.3556(2) 0.4148(4) 0.2586(2) 0.0226(9) Uani 1 1 d . . .
C27 C 0.0934(2) 0.1072(4) 0.2418(2) 0.0227(8) Uani 1 1 d . . .
C28 C 0.1057(2) -0.1349(4) 0.3107(2) 0.0302(10) Uani 1 1 d . . .
C29 C 0.1377(3) -0.0492(4) 0.3866(3) 0.0384(11) Uani 1 1 d . . .
H10 H 0.0052(19) 0.821(4) -0.0079(15) 0.039(12) Uiso 1 1 d D . .
H11 H 0.038(2) 0.707(2) 0.064(2) 0.038(11) Uiso 1 1 d D . .
H12 H 0.1815(19) 0.709(3) 0.1685(19) 0.016(8) Uiso 1 1 d . . .
H13 H 0.314(2) 0.741(3) 0.1720(19) 0.011(8) Uiso 1 1 d . . .
H15 H 0.226(2) 1.001(4) -0.061(2) 0.027(9) Uiso 1 1 d . . .
H16 H 0.087(2) 0.961(3) -0.070(2) 0.021(9) Uiso 1 1 d . . .
H17 H 0.431(2) 0.435(4) 0.0640(14) 0.027(10) Uiso 1 1 d D . .
H18 H 0.397(2) 0.284(4) -0.067(2) 0.027(10) Uiso 1 1 d . . .
H19 H 0.340(2) 0.450(4) -0.209(2) 0.042(12) Uiso 1 1 d . . .
H20 H 0.4873(18) 0.360(4) 0.2329(17) 0.043(12) Uiso 1 1 d D . .
H21 H 0.456(2) 0.232(2) 0.1679(19) 0.017(9) Uiso 1 1 d D . .
H22 H 0.309(2) 0.225(4) 0.058(2) 0.044(11) Uiso 1 1 d . . .
H23 H 0.173(2) 0.244(4) 0.066(2) 0.019(9) Uiso 1 1 d . . .
H25 H 0.270(2) 0.482(4) 0.310(2) 0.023(9) Uiso 1 1 d . . .
H26 H 0.403(2) 0.447(4) 0.312(2) 0.026(9) Uiso 1 1 d . . .
H27 H 0.063(3) -0.088(4) 0.1721(16) 0.059(13) Uiso 1 1 d D . .
H28 H 0.097(2) -0.241(4) 0.301(2) 0.027(10) Uiso 1 1 d . . .
H29 H 0.161(2) -0.073(4) 0.451(2) 0.039(11) 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
S11 O12 1.442(2) . ?
S11 O11 1.448(2) . ?
S11 N12 1.588(3) . ?
S11 C14 1.760(4) . ?
S12 C19 1.725(4) . ?
S12 C17 1.744(3) . ?
N11 C11 1.406(4) . ?
N11 H10 0.881(18) . ?
N11 H11 0.887(18) . ?
N12 C17 1.328(4) . ?
N13 C17 1.340(4) . ?
N13 C18 1.376(4) . ?
N13 H17 0.884(17) . ?
C11 C16 1.393(4) . ?
C11 C12 1.401(5) . ?
C12 C13 1.374(5) . ?
C12 H12 0.95(3) . ?
C13 C14 1.388(4) . ?
C13 H13 0.92(3) . ?
C14 C15 1.395(5) . ?
C15 C16 1.365(5) . ?
C15 H15 0.94(3) . ?
C16 H16 0.97(3) . ?
C18 C19 1.324(5) . ?
C18 H18 0.92(3) . ?
C19 H19 0.89(3) . ?
S21 O21 1.440(2) . ?
S21 O22 1.441(2) . ?
S21 N22 1.600(3) . ?
S21 C24 1.755(4) . ?
S22 C29 1.736(4) . ?
S22 C27 1.736(3) . ?
N21 C21 1.401(5) . ?
N21 H20 0.880(18) . ?
N21 H21 0.854(18) . ?
N22 C27 1.339(4) . ?
N23 C27 1.333(4) . ?
N23 C28 1.384(4) . ?
N23 H27 0.888(18) . ?
C21 C26 1.395(4) . ?
C21 C22 1.396(5) . ?
C22 C23 1.376(5) . ?
C22 H22 1.01(3) . ?
C23 C24 1.404(4) . ?
C23 H23 0.94(3) . ?
C24 C25 1.392(5) . ?
C25 C26 1.381(5) . ?
C25 H25 0.97(3) . ?
C26 H26 0.96(3) . ?
C28 C29 1.310(5) . ?
C28 H28 0.92(3) . ?
C29 H29 0.94(3) . ?
 
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
O12 S11 O11 116.16(14) . . ?
O12 S11 N12 114.29(14) . . ?
O11 S11 N12 105.58(14) . . ?
O12 S11 C14 107.78(15) . . ?
O11 S11 C14 107.50(14) . . ?
N12 S11 C14 104.78(16) . . ?
C19 S12 C17 90.50(18) . . ?
C11 N11 H10 110(2) . . ?
C11 N11 H11 110(3) . . ?
H10 N11 H11 108(3) . . ?
C17 N12 S11 119.8(2) . . ?
C17 N13 C18 115.5(3) . . ?
C17 N13 H17 120(2) . . ?
C18 N13 H17 124(2) . . ?
C16 C11 C12 118.4(4) . . ?
C16 C11 N11 121.9(3) . . ?
C12 C11 N11 119.7(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 122.7(19) . . ?
C11 C12 H12 117(2) . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 117.4(19) . . ?
C14 C13 H13 122.6(19) . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 S11 119.1(3) . . ?
C15 C14 S11 121.4(3) . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 124(2) . . ?
C14 C15 H15 116(2) . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 121.3(19) . . ?
C11 C16 H16 117.8(19) . . ?
N12 C17 N13 120.4(3) . . ?
N12 C17 S12 130.3(3) . . ?
N13 C17 S12 109.2(2) . . ?
C19 C18 N13 112.7(4) . . ?
C19 C18 H18 131(2) . . ?
N13 C18 H18 117(2) . . ?
C18 C19 S12 112.1(3) . . ?
C18 C19 H19 129(2) . . ?
S12 C19 H19 119(2) . . ?
O21 S21 O22 117.51(14) . . ?
O21 S21 N22 105.62(14) . . ?
O22 S21 N22 113.13(14) . . ?
O21 S21 C24 107.53(14) . . ?
O22 S21 C24 107.36(15) . . ?
N22 S21 C24 104.88(15) . . ?
C29 S22 C27 90.30(17) . . ?
C21 N21 H20 114(2) . . ?
C21 N21 H21 112(2) . . ?
H20 N21 H21 112(3) . . ?
C27 N22 S21 119.8(2) . . ?
C27 N23 C28 114.9(3) . . ?
C27 N23 H27 120(3) . . ?
C28 N23 H27 125(3) . . ?
C26 C21 C22 119.3(4) . . ?
C26 C21 N21 122.1(3) . . ?
C22 C21 N21 118.6(3) . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 121(2) . . ?
C21 C22 H22 118(2) . . ?
C22 C23 C24 120.5(4) . . ?
C22 C23 H23 124(2) . . ?
C24 C23 H23 116(2) . . ?
C25 C24 C23 119.0(3) . . ?
C25 C24 S21 122.1(3) . . ?
C23 C24 S21 118.9(3) . . ?
C26 C25 C24 120.5(3) . . ?
C26 C25 H25 119(2) . . ?
C24 C25 H25 121(2) . . ?
C25 C26 C21 120.4(3) . . ?
C25 C26 H26 121(2) . . ?
C21 C26 H26 119(2) . . ?
N23 C27 N22 120.4(3) . . ?
N23 C27 S22 109.8(2) . . ?
N22 C27 S22 129.8(3) . . ?
C29 C28 N23 113.2(3) . . ?
C29 C28 H28 133(2) . . ?
N23 C28 H28 114(2) . . ?
C28 C29 S22 111.7(3) . . ?
C28 C29 H29 133(2) . . ?
S22 C29 H29 115(2) . . ?
 
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
O12 S11 N12 C17 -39.9(3) . . . . ?
O11 S11 N12 C17 -168.8(3) . . . . ?
C14 S11 N12 C17 77.8(3) . . . . ?
C16 C11 C12 C13 -2.0(5) . . . . ?
N11 C11 C12 C13 179.7(3) . . . . ?
C11 C12 C13 C14 1.2(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C12 C13 C14 S11 -179.6(2) . . . . ?
O12 S11 C14 C13 173.1(2) . . . . ?
O11 S11 C14 C13 -61.0(3) . . . . ?
N12 S11 C14 C13 51.0(3) . . . . ?
O12 S11 C14 C15 -6.4(3) . . . . ?
O11 S11 C14 C15 119.5(3) . . . . ?
N12 S11 C14 C15 -128.5(3) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
S11 C14 C15 C16 179.4(2) . . . . ?
C14 C15 C16 C11 -0.8(5) . . . . ?
C12 C11 C16 C15 1.8(5) . . . . ?
N11 C11 C16 C15 -180.0(3) . . . . ?
S11 N12 C17 N13 -163.1(3) . . . . ?
S11 N12 C17 S12 19.5(5) . . . . ?
C18 N13 C17 N12 -178.6(3) . . . . ?
C18 N13 C17 S12 -0.7(4) . . . . ?
C19 S12 C17 N12 178.4(4) . . . . ?
C19 S12 C17 N13 0.7(3) . . . . ?
C17 N13 C18 C19 0.2(5) . . . . ?
N13 C18 C19 S12 0.4(5) . . . . ?
C17 S12 C19 C18 -0.6(4) . . . . ?
O21 S21 N22 C27 -166.3(3) . . . . ?
O22 S21 N22 C27 -36.4(3) . . . . ?
C24 S21 N22 C27 80.2(3) . . . . ?
C26 C21 C22 C23 -1.0(5) . . . . ?
N21 C21 C22 C23 -179.6(3) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
C22 C23 C24 S21 178.9(3) . . . . ?
O21 S21 C24 C25 121.5(3) . . . . ?
O22 S21 C24 C25 -5.8(3) . . . . ?
N22 S21 C24 C25 -126.4(3) . . . . ?
O21 S21 C24 C23 -57.4(3) . . . . ?
O22 S21 C24 C23 175.3(2) . . . . ?
N22 S21 C24 C23 54.7(3) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
S21 C24 C25 C26 -178.7(2) . . . . ?
C24 C25 C26 C21 -0.7(5) . . . . ?
C22 C21 C26 C25 1.2(5) . . . . ?
N21 C21 C26 C25 179.7(3) . . . . ?
C28 N23 C27 N22 179.1(3) . . . . ?
C28 N23 C27 S22 -1.3(4) . . . . ?
S21 N22 C27 N23 -165.8(3) . . . . ?
S21 N22 C27 S22 14.7(5) . . . . ?
C29 S22 C27 N23 1.1(3) . . . . ?
C29 S22 C27 N22 -179.3(4) . . . . ?
C27 N23 C28 C29 0.9(5) . . . . ?
N23 C28 C29 S22 0.0(5) . . . . ?
C27 S22 C29 C28 -0.6(4) . . . . ?
 
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
N11 H10 N22  0.881(18) 2.33(2) 3.184(4) 162(3) 3_565
N11 H11 O21  0.887(18) 2.14(2) 3.001(4) 164(3) .
N13 H17 N21  0.884(17) 1.978(19) 2.846(4) 167(3) .
N21 H20 O11  0.880(18) 2.14(2) 3.005(4) 168(3) 2_645
N21 H21 O11  0.854(18) 2.18(2) 2.977(4) 155(3) 1_545
N23 H27 N11  0.888(18) 2.02(2) 2.899(4) 171(4) 1_545
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.434
_refine_diff_density_min   -0.479
_refine_diff_density_rms    0.077
