 
data_01ale005
 
_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/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                    10.7740(10)
_cell_length_b                    8.4670(10)
_cell_length_c                    11.3670(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.650(10)
_cell_angle_gamma                 90.00
_cell_volume                      1036.51(18)
_cell_formula_units_Z             4
_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           0.22
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.636
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              528
_exptl_absorpt_coefficient_mu     0.500
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8851
_exptl_absorpt_correction_T_max   0.9706
_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             7262
_diffrn_reflns_av_R_equivalents   0.0756
_diffrn_reflns_av_sigmaI/netI     0.0643
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.00
_diffrn_reflns_theta_max          26.00
_reflns_number_total              2026
_reflns_number_gt                 1655
_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)+(0.0515P)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          2026
_refine_ls_number_parameters      181
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0555
_refine_ls_R_factor_gt            0.0382
_refine_ls_wR_factor_ref          0.0959
_refine_ls_wR_factor_gt           0.0910
_refine_ls_goodness_of_fit_ref    1.053
_refine_ls_restrained_S_all       1.053
_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 0.48228(5) 0.11472(6) 0.26293(4) 0.01403(18) Uani 1 1 d . . .
S12 S 0.34389(6) 0.34250(6) 0.06718(5) 0.02392(19) Uani 1 1 d . . .
O11 O 0.49723(14) 0.03463(15) 0.37404(12) 0.0190(4) Uani 1 1 d . . .
O12 O 0.40188(14) 0.04220(15) 0.17448(12) 0.0181(4) Uani 1 1 d . . .
N11 N 0.98740(17) 0.1901(2) 0.07072(16) 0.0163(4) Uani 1 1 d . . .
N12 N 0.44221(16) 0.29157(19) 0.29397(14) 0.0146(4) Uani 1 1 d . . .
N13 N 0.38859(17) 0.54216(19) 0.22789(15) 0.0144(4) Uani 1 1 d . . .
C11 C 0.8672(2) 0.1691(2) 0.11378(17) 0.0135(4) Uani 1 1 d . . .
C12 C 0.8393(2) 0.2310(2) 0.22415(18) 0.0152(5) Uani 1 1 d . . .
C13 C 0.7221(2) 0.2152(2) 0.26780(17) 0.0144(5) Uani 1 1 d . . .
C14 C 0.63056(19) 0.1339(2) 0.20310(17) 0.0134(4) Uani 1 1 d . . .
C15 C 0.6582(2) 0.0682(2) 0.09514(17) 0.0141(4) Uani 1 1 d . . .
C16 C 0.7761(2) 0.0845(2) 0.05115(17) 0.0137(4) Uani 1 1 d . . .
C17 C 0.39804(19) 0.3863(2) 0.20909(17) 0.0145(4) Uani 1 1 d . . .
C18 C 0.3421(2) 0.6287(3) 0.13377(19) 0.0188(5) Uani 1 1 d . . .
C19 C 0.3143(2) 0.5414(3) 0.0404(2) 0.0270(6) Uani 1 1 d . . .
H10 H 0.989(2) 0.164(3) -0.005(2) 0.027(7) Uiso 1 1 d . . .
H11 H 1.010(2) 0.283(3) 0.082(2) 0.027(7) Uiso 1 1 d . . .
H12 H 0.900(2) 0.289(3) 0.2670(19) 0.017(6) Uiso 1 1 d . . .
H13 H 0.704(2) 0.263(2) 0.346(2) 0.016(5) Uiso 1 1 d . . .
H15 H 0.595(2) 0.013(3) 0.053(2) 0.024(6) Uiso 1 1 d . . .
H16 H 0.794(2) 0.038(2) -0.0242(19) 0.012(5) Uiso 1 1 d . . .
H17 H 0.4147(19) 0.581(2) 0.2943(18) 0.008(5) Uiso 1 1 d . . .
H18 H 0.337(2) 0.740(3) 0.144(2) 0.028(6) Uiso 1 1 d . . .
H19 H 0.290(2) 0.562(3) -0.032(2) 0.032(7) 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 O11 1.4384(14) . ?
S11 O12 1.4449(14) . ?
S11 N12 1.6006(17) . ?
S11 C14 1.762(2) . ?
S12 C19 1.739(2) . ?
S12 C17 1.740(2) . ?
N11 C11 1.409(3) . ?
N11 H10 0.89(3) . ?
N11 H11 0.84(3) . ?
N12 C17 1.332(3) . ?
N13 C17 1.341(3) . ?
N13 C18 1.379(3) . ?
N13 H17 0.86(2) . ?
C11 C16 1.394(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.94(2) . ?
C13 C14 1.395(3) . ?
C13 H13 1.00(2) . ?
C14 C15 1.387(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.95(2) . ?
C16 H16 0.97(2) . ?
C18 C19 1.321(3) . ?
C18 H18 0.95(3) . ?
C19 H19 0.88(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
O11 S11 O12 117.41(9) . . ?
O11 S11 N12 105.76(9) . . ?
O12 S11 N12 113.01(9) . . ?
O11 S11 C14 107.60(9) . . ?
O12 S11 C14 107.62(9) . . ?
N12 S11 C14 104.61(9) . . ?
C19 S12 C17 90.61(11) . . ?
C11 N11 H10 110.6(17) . . ?
C11 N11 H11 109.6(17) . . ?
H10 N11 H11 112(2) . . ?
C17 N12 S11 119.79(14) . . ?
C17 N13 C18 115.27(18) . . ?
C17 N13 H17 119.4(13) . . ?
C18 N13 H17 125.3(13) . . ?
C16 C11 C12 118.9(2) . . ?
C16 C11 N11 121.88(19) . . ?
C12 C11 N11 119.18(19) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7(14) . . ?
C11 C12 H12 119.6(14) . . ?
C12 C13 C14 119.99(19) . . ?
C12 C13 H13 118.8(13) . . ?
C14 C13 H13 121.2(13) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 S11 121.63(16) . . ?
C13 C14 S11 118.50(15) . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 121.6(14) . . ?
C14 C15 H15 118.3(14) . . ?
C15 C16 C11 120.43(19) . . ?
C15 C16 H16 119.1(13) . . ?
C11 C16 H16 120.5(13) . . ?
N12 C17 N13 120.29(17) . . ?
N12 C17 S12 130.27(15) . . ?
N13 C17 S12 109.43(15) . . ?
C19 C18 N13 113.2(2) . . ?
C19 C18 H18 129.5(14) . . ?
N13 C18 H18 117.3(14) . . ?
C18 C19 S12 111.44(18) . . ?
C18 C19 H19 134.4(16) . . ?
S12 C19 H19 114.0(16) . . ?
 
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
O11 S11 N12 C17 -166.91(16) . . . . ?
O12 S11 N12 C17 -37.16(19) . . . . ?
C14 S11 N12 C17 79.62(18) . . . . ?
C16 C11 C12 C13 -3.1(3) . . . . ?
N11 C11 C12 C13 178.76(17) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C12 C13 C14 S11 179.36(15) . . . . ?
O11 S11 C14 C15 120.15(17) . . . . ?
O12 S11 C14 C15 -7.25(19) . . . . ?
N12 S11 C14 C15 -127.69(16) . . . . ?
O11 S11 C14 C13 -58.79(16) . . . . ?
O12 S11 C14 C13 173.80(14) . . . . ?
N12 S11 C14 C13 53.37(17) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
S11 C14 C15 C16 -179.49(14) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C12 C11 C16 C15 2.9(3) . . . . ?
N11 C11 C16 C15 -178.98(17) . . . . ?
S11 N12 C17 N13 -166.05(16) . . . . ?
S11 N12 C17 S12 15.0(3) . . . . ?
C18 N13 C17 N12 179.78(19) . . . . ?
C18 N13 C17 S12 -1.0(2) . . . . ?
C19 S12 C17 N12 -179.7(2) . . . . ?
C19 S12 C17 N13 1.20(17) . . . . ?
C17 N13 C18 C19 0.2(3) . . . . ?
N13 C18 C19 S12 0.8(3) . . . . ?
C17 S12 C19 C18 -1.1(2) . . . . ?
 
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 N12  0.89(3) 2.36(3) 3.173(2) 153(2) 4_665
N11 H11 O11  0.84(3) 2.19(3) 2.988(2) 160(2) 2_655
N13 H17 N11  0.86(2) 2.06(2) 2.902(3) 166.3(19) 2_655
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.430
_refine_diff_density_min   -0.591
_refine_diff_density_rms    0.111
