 
data_00ale002
 
_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                    10.534(2)
_cell_length_b                    12.936(3)
_cell_length_c                    17.191(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  107.77(3)
_cell_angle_gamma                 90.00
_cell_volume                      2230.8(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           0.25
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.520
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1056
_exptl_absorpt_coefficient_mu     0.465
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8926
_exptl_absorpt_correction_T_max   0.9637
_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          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             19523
_diffrn_reflns_av_R_equivalents   0.0878
_diffrn_reflns_av_sigmaI/netI     0.0627
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.94
_diffrn_reflns_theta_max          25.03
_reflns_number_total              3938
_reflns_number_gt                 2890
_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)+(0.0521P)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          3938
_refine_ls_number_parameters      361
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0646
_refine_ls_R_factor_gt            0.0400
_refine_ls_wR_factor_ref          0.1016
_refine_ls_wR_factor_gt           0.0917
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_restrained_S_all       1.032
_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 0.69239(6) 0.57187(5) -0.08959(4) 0.02329(18) Uani 1 1 d . . .
S12 S 0.84723(7) 0.75569(5) 0.03577(4) 0.0300(2) Uani 1 1 d . . .
S21 S 0.81776(6) 0.07347(5) 0.11850(4) 0.02438(19) Uani 1 1 d . . .
S22 S 0.63514(7) 0.08306(7) -0.07338(5) 0.0379(2) Uani 1 1 d . . .
O11 O 0.66220(17) 0.46787(14) -0.11992(11) 0.0313(5) Uani 1 1 d . . .
O12 O 0.62019(17) 0.61186(15) -0.03712(11) 0.0320(5) Uani 1 1 d . . .
O21 O 0.91444(18) 0.03367(14) 0.19157(11) 0.0337(5) Uani 1 1 d . . .
O22 O 0.68019(17) 0.04393(14) 0.10245(11) 0.0315(5) Uani 1 1 d . . .
N11 N 0.5716(2) 0.8423(2) -0.38022(16) 0.0311(6) Uani 1 1 d . . .
N12 N 0.85087(19) 0.57011(16) -0.04551(12) 0.0217(5) Uani 1 1 d . . .
N13 N 1.0391(2) 0.63256(19) 0.05217(14) 0.0261(5) Uani 1 1 d . . .
N21 N 0.8434(3) 0.52760(19) 0.15165(15) 0.0295(6) Uani 1 1 d . . .
N22 N 0.8744(2) 0.03564(16) 0.04598(13) 0.0243(5) Uani 1 1 d . . .
N23 N 0.8466(2) 0.01147(17) -0.09147(13) 0.0251(5) Uani 1 1 d . . .
C11 C 0.5977(2) 0.7778(2) -0.31347(16) 0.0234(6) Uani 1 1 d . . .
C12 C 0.6640(2) 0.6845(2) -0.31092(16) 0.0224(6) Uani 1 1 d . . .
C13 C 0.6944(2) 0.6225(2) -0.24236(15) 0.0210(6) Uani 1 1 d . . .
C14 C 0.6594(2) 0.65395(19) -0.17450(15) 0.0208(6) Uani 1 1 d . . .
C15 C 0.5924(3) 0.7465(2) -0.17654(17) 0.0256(6) Uani 1 1 d . . .
C16 C 0.5602(3) 0.8072(2) -0.24508(16) 0.0268(6) Uani 1 1 d . . .
C17 C 0.9102(2) 0.64180(19) 0.00850(15) 0.0215(6) Uani 1 1 d . . .
C18 C 1.0876(3) 0.7089(2) 0.10979(18) 0.0326(7) Uani 1 1 d . . .
C19 C 0.9986(3) 0.7810(2) 0.10922(19) 0.0337(7) Uani 1 1 d . . .
C21 C 0.8373(2) 0.4232(2) 0.13989(15) 0.0224(6) Uani 1 1 d . . .
C22 C 0.9523(3) 0.3621(2) 0.16839(16) 0.0254(6) Uani 1 1 d . . .
C23 C 0.9471(3) 0.2572(2) 0.15965(17) 0.0253(6) Uani 1 1 d . . .
C24 C 0.8260(2) 0.2082(2) 0.12317(15) 0.0210(6) Uani 1 1 d . . .
C25 C 0.7110(3) 0.2675(2) 0.09268(16) 0.0250(6) Uani 1 1 d . . .
C26 C 0.7169(3) 0.3732(2) 0.10050(17) 0.0274(6) Uani 1 1 d . . .
C27 C 0.7984(2) 0.0408(2) -0.03194(16) 0.0235(6) Uani 1 1 d . . .
C28 C 0.7626(3) 0.0268(2) -0.16958(18) 0.0307(7) Uani 1 1 d . . .
C29 C 0.6454(3) 0.0657(2) -0.17146(18) 0.0371(7) Uani 1 1 d . . .
H10 H 0.501(3) 0.890(3) -0.386(2) 0.054(10) Uiso 1 1 d . . .
H11 H 0.580(3) 0.815(2) -0.4230(19) 0.039(9) Uiso 1 1 d . . .
H12 H 0.685(2) 0.6612(19) -0.3570(16) 0.022(7) Uiso 1 1 d . . .
H13 H 0.739(2) 0.5590(19) -0.2414(15) 0.019(7) Uiso 1 1 d . . .
H15 H 0.566(2) 0.7633(18) -0.1333(16) 0.018(7) Uiso 1 1 d . . .
H16 H 0.507(2) 0.867(2) -0.2491(16) 0.029(7) Uiso 1 1 d . . .
H17 H 1.083(3) 0.578(2) 0.0520(17) 0.029(8) Uiso 1 1 d . . .
H18 H 1.174(3) 0.700(2) 0.1446(18) 0.038(8) Uiso 1 1 d . . .
H19 H 1.008(2) 0.837(2) 0.1424(16) 0.026(7) Uiso 1 1 d . . .
H20 H 0.764(3) 0.566(2) 0.1360(17) 0.030(8) Uiso 1 1 d . . .
H21 H 0.919(3) 0.555(2) 0.1818(19) 0.039(9) Uiso 1 1 d . . .
H22 H 1.033(3) 0.397(2) 0.1948(17) 0.029(7) Uiso 1 1 d . . .
H23 H 1.022(3) 0.217(2) 0.1784(16) 0.029(7) Uiso 1 1 d . . .
H25 H 0.629(3) 0.235(2) 0.0700(18) 0.035(8) Uiso 1 1 d . . .
H26 H 0.640(3) 0.416(2) 0.0812(17) 0.032(8) Uiso 1 1 d . . .
H27 H 0.929(3) -0.011(2) -0.0800(18) 0.043(9) Uiso 1 1 d . . .
H28 H 0.793(3) 0.006(2) -0.2127(17) 0.029(7) Uiso 1 1 d . . .
H29 H 0.569(3) 0.079(3) -0.216(2) 0.067(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 1.4417(19) . ?
S11 O11 1.4427(19) . ?
S11 N12 1.609(2) . ?
S11 C14 1.752(3) . ?
S12 C19 1.737(3) . ?
S12 C17 1.738(3) . ?
S21 O22 1.4417(18) . ?
S21 O21 1.4489(19) . ?
S21 N22 1.613(2) . ?
S21 C24 1.746(3) . ?
S22 C27 1.736(2) . ?
S22 C29 1.737(3) . ?
N11 C11 1.377(3) . ?
N11 H10 0.95(3) . ?
N11 H11 0.84(3) . ?
N12 C17 1.326(3) . ?
N13 C17 1.342(3) . ?
N13 C18 1.382(4) . ?
N13 H17 0.85(3) . ?
N21 C21 1.365(3) . ?
N21 H20 0.94(3) . ?
N21 H21 0.88(3) . ?
N22 C27 1.336(3) . ?
N23 C27 1.329(3) . ?
N23 C28 1.378(3) . ?
N23 H27 0.88(3) . ?
C11 C12 1.388(4) . ?
C11 C16 1.403(4) . ?
C12 C13 1.380(4) . ?
C12 H12 0.94(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.95(2) . ?
C14 C15 1.385(4) . ?
C15 C16 1.369(4) . ?
C15 H15 0.90(2) . ?
C16 H16 0.94(3) . ?
C18 C19 1.320(4) . ?
C18 H18 0.93(3) . ?
C19 H19 0.91(3) . ?
C21 C26 1.400(4) . ?
C21 C22 1.403(4) . ?
C22 C23 1.364(4) . ?
C22 H22 0.95(3) . ?
C23 C24 1.391(4) . ?
C23 H23 0.92(3) . ?
C24 C25 1.394(4) . ?
C25 C26 1.373(4) . ?
C25 H25 0.94(3) . ?
C26 H26 0.95(3) . ?
C28 C29 1.324(4) . ?
C28 H28 0.93(3) . ?
C29 H29 0.94(4) . ?
 
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 117.42(11) . . ?
O12 S11 N12 112.33(11) . . ?
O11 S11 N12 103.86(11) . . ?
O12 S11 C14 107.19(12) . . ?
O11 S11 C14 107.36(12) . . ?
N12 S11 C14 108.32(11) . . ?
C19 S12 C17 90.85(13) . . ?
O22 S21 O21 118.12(12) . . ?
O22 S21 N22 111.02(11) . . ?
O21 S21 N22 103.55(11) . . ?
O22 S21 C24 107.83(11) . . ?
O21 S21 C24 107.64(12) . . ?
N22 S21 C24 108.27(11) . . ?
C27 S22 C29 90.58(14) . . ?
C11 N11 H10 115.7(19) . . ?
C11 N11 H11 115(2) . . ?
H10 N11 H11 118(3) . . ?
C17 N12 S11 121.28(18) . . ?
C17 N13 C18 115.3(2) . . ?
C17 N13 H17 122.2(19) . . ?
C18 N13 H17 121.2(19) . . ?
C21 N21 H20 118.8(17) . . ?
C21 N21 H21 118.5(19) . . ?
H20 N21 H21 122(3) . . ?
C27 N22 S21 120.65(18) . . ?
C27 N23 C28 115.3(2) . . ?
C27 N23 H27 120(2) . . ?
C28 N23 H27 124(2) . . ?
N11 C11 C12 121.6(2) . . ?
N11 C11 C16 119.9(3) . . ?
C12 C11 C16 118.5(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 118.8(15) . . ?
C11 C12 H12 120.1(15) . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.3(15) . . ?
C14 C13 H13 120.0(15) . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 S11 120.99(19) . . ?
C13 C14 S11 119.1(2) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 121.0(16) . . ?
C14 C15 H15 118.3(16) . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 121.2(16) . . ?
C11 C16 H16 118.2(16) . . ?
N12 C17 N13 120.6(2) . . ?
N12 C17 S12 130.15(19) . . ?
N13 C17 S12 109.21(19) . . ?
C19 C18 N13 113.2(3) . . ?
C19 C18 H18 130.0(18) . . ?
N13 C18 H18 116.7(18) . . ?
C18 C19 S12 111.4(2) . . ?
C18 C19 H19 128.3(17) . . ?
S12 C19 H19 120.2(16) . . ?
N21 C21 C26 121.5(2) . . ?
N21 C21 C22 120.6(2) . . ?
C26 C21 C22 117.9(3) . . ?
C23 C22 C21 121.3(2) . . ?
C23 C22 H22 121.9(16) . . ?
C21 C22 H22 116.8(16) . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 121.7(17) . . ?
C24 C23 H23 118.0(17) . . ?
C23 C24 C25 119.4(3) . . ?
C23 C24 S21 120.1(2) . . ?
C25 C24 S21 120.5(2) . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 120.1(17) . . ?
C24 C25 H25 119.6(17) . . ?
C25 C26 C21 120.9(3) . . ?
C25 C26 H26 122.1(17) . . ?
C21 C26 H26 117.0(17) . . ?
N23 C27 N22 120.3(2) . . ?
N23 C27 S22 109.70(19) . . ?
N22 C27 S22 130.0(2) . . ?
C29 C28 N23 113.2(3) . . ?
C29 C28 H28 129.3(17) . . ?
N23 C28 H28 117.4(16) . . ?
C28 C29 S22 111.1(2) . . ?
C28 C29 H29 130(2) . . ?
S22 C29 H29 118(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 -33.3(2) . . . . ?
O11 S11 N12 C17 -161.2(2) . . . . ?
C14 S11 N12 C17 84.9(2) . . . . ?
O22 S21 N22 C27 39.3(2) . . . . ?
O21 S21 N22 C27 167.0(2) . . . . ?
C24 S21 N22 C27 -78.9(2) . . . . ?
N11 C11 C12 C13 177.3(2) . . . . ?
C16 C11 C12 C13 -1.0(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C12 C13 C14 S11 177.32(19) . . . . ?
O12 S11 C14 C15 9.0(2) . . . . ?
O11 S11 C14 C15 136.0(2) . . . . ?
N12 S11 C14 C15 -112.4(2) . . . . ?
O12 S11 C14 C13 -167.18(19) . . . . ?
O11 S11 C14 C13 -40.2(2) . . . . ?
N12 S11 C14 C13 71.4(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
S11 C14 C15 C16 -176.1(2) . . . . ?
C14 C15 C16 C11 -1.7(4) . . . . ?
N11 C11 C16 C15 -176.2(3) . . . . ?
C12 C11 C16 C15 2.2(4) . . . . ?
S11 N12 C17 N13 171.72(18) . . . . ?
S11 N12 C17 S12 -8.5(3) . . . . ?
C18 N13 C17 N12 -176.4(2) . . . . ?
C18 N13 C17 S12 3.8(3) . . . . ?
C19 S12 C17 N12 177.3(3) . . . . ?
C19 S12 C17 N13 -2.9(2) . . . . ?
C17 N13 C18 C19 -2.8(4) . . . . ?
N13 C18 C19 S12 0.4(3) . . . . ?
C17 S12 C19 C18 1.4(2) . . . . ?
N21 C21 C22 C23 177.7(2) . . . . ?
C26 C21 C22 C23 -1.3(4) . . . . ?
C21 C22 C23 C24 -1.1(4) . . . . ?
C22 C23 C24 C25 2.6(4) . . . . ?
C22 C23 C24 S21 -175.5(2) . . . . ?
O22 S21 C24 C23 162.1(2) . . . . ?
O21 S21 C24 C23 33.6(2) . . . . ?
N22 S21 C24 C23 -77.7(2) . . . . ?
O22 S21 C24 C25 -16.0(2) . . . . ?
O21 S21 C24 C25 -144.4(2) . . . . ?
N22 S21 C24 C25 104.2(2) . . . . ?
C23 C24 C25 C26 -1.7(4) . . . . ?
S21 C24 C25 C26 176.5(2) . . . . ?
C24 C25 C26 C21 -0.8(4) . . . . ?
N21 C21 C26 C25 -176.7(2) . . . . ?
C22 C21 C26 C25 2.2(4) . . . . ?
C28 N23 C27 N22 -175.7(2) . . . . ?
C28 N23 C27 S22 3.8(3) . . . . ?
S21 N22 C27 N23 178.61(19) . . . . ?
S21 N22 C27 S22 -0.8(4) . . . . ?
C29 S22 C27 N23 -3.5(2) . . . . ?
C29 S22 C27 N22 175.9(3) . . . . ?
C27 N23 C28 C29 -2.0(4) . . . . ?
N23 C28 C29 S22 -0.9(4) . . . . ?
C27 S22 C29 C28 2.5(3) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.315
_refine_diff_density_min   -0.475
_refine_diff_density_rms    0.077
