 
data_00tam075
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H17 N5 O2 S2'
_chemical_formula_weight          339.44
 
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                    12.179(2)
_cell_length_b                    9.6098(19)
_cell_length_c                    13.353(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  101.92(3)
_cell_angle_gamma                 90.00
_cell_volume                      1529.1(5)
_cell_formula_units_Z             4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       2.96
_cell_measurement_theta_max       25.03
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.125
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.474
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              712
_exptl_absorpt_coefficient_mu     0.363
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.897
_exptl_absorpt_correction_T_max   0.956
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD'
_diffrn_measurement_method        'φ and 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             9929
_diffrn_reflns_av_R_equivalents   0.0387
_diffrn_reflns_av_sigmaI/netI     0.0363
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          25.03
_reflns_number_total              2697
_reflns_number_gt                 2267
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection      
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_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)+(0.0508P)²+0.5356P] 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      SHELXL
_refine_ls_extinction_coef        0.0050(15)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2697
_refine_ls_number_parameters      268
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0436
_refine_ls_R_factor_gt            0.0347
_refine_ls_wR_factor_ref          0.0917
_refine_ls_wR_factor_gt           0.0863
_refine_ls_goodness_of_fit_ref    1.034
_refine_ls_restrained_S_all       1.034
_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
S12 S 1.00175(4) 0.13290(5) 0.84697(5) 0.03327(19) Uani 1 1 d . . .
C17 C 0.89695(16) 0.22709(18) 0.88868(14) 0.0204(4) Uani 1 1 d . . .
N13 N 0.92018(14) 0.35911(15) 0.90391(13) 0.0275(4) Uani 1 1 d . . .
N22 N 0.74934(14) -0.37912(18) 0.88186(13) 0.0266(4) Uani 1 1 d . . .
C24 C 0.68270(17) -0.28122(19) 0.89945(15) 0.0263(5) Uani 1 1 d . . .
C22 C 0.85219(18) -0.3227(2) 0.85676(18) 0.0272(5) Uani 1 1 d . . .
C18 C 1.02480(18) 0.3880(2) 0.88296(18) 0.0319(5) Uani 1 1 d . . .
C19 C 1.0803(2) 0.2824(2) 0.85201(18) 0.0334(5) Uani 1 1 d . . .
C21 C 0.83492(19) -0.1661(2) 0.86401(18) 0.0303(5) Uani 1 1 d . . .
C25 C 0.5739(2) -0.3080(3) 0.9273(2) 0.0391(6) Uani 1 1 d . . .
H13 H 0.8962(15) 0.1492(19) 1.1058(14) 0.014(5) Uiso 1 1 d . . .
H16 H 0.7164(17) 0.512(2) 1.2385(15) 0.028(5) Uiso 1 1 d . . .
H12 H 0.9641(18) 0.2265(19) 1.2704(15) 0.024(5) Uiso 1 1 d . . .
H15 H 0.6494(17) 0.4406(19) 1.0699(15) 0.021(5) Uiso 1 1 d . . .
H22A H 0.860(2) -0.352(2) 0.7878(19) 0.041(6) Uiso 1 1 d . . .
H22B H 0.9146(19) -0.350(2) 0.9041(18) 0.031(6) Uiso 1 1 d . . .
H21A H 0.8288(19) -0.119(2) 0.7968(19) 0.041(6) Uiso 1 1 d . . .
H25A H 0.550(2) -0.396(3) 0.906(2) 0.049(7) Uiso 1 1 d . . .
H19 H 1.148(2) 0.279(2) 0.8361(18) 0.040(7) Uiso 1 1 d . . .
H21B H 0.8904(18) -0.123(2) 0.9177(17) 0.026(5) Uiso 1 1 d . . .
H25B H 0.531(3) -0.227(3) 0.900(2) 0.071(9) Uiso 1 1 d . . .
H11 H 0.956(2) 0.404(2) 1.3952(18) 0.035(7) Uiso 1 1 d . . .
H10 H 0.858(2) 0.497(3) 1.3916(18) 0.042(7) Uiso 1 1 d . . .
H25C H 0.583(2) -0.299(3) 1.000(2) 0.052(8) Uiso 1 1 d . . .
H18 H 1.051(2) 0.477(2) 0.8933(17) 0.037(6) Uiso 1 1 d . . .
H21N H 0.692(2) -0.088(3) 0.898(2) 0.055(8) Uiso 1 1 d . . .
H22 H 0.7349(19) -0.458(3) 0.8820(16) 0.032(6) Uiso 1 1 d . . .
S11 S 0.71038(4) 0.22524(4) 0.94674(3) 0.01863(17) Uani 1 1 d . . .
O11 O 0.63130(11) 0.11375(12) 0.95588(10) 0.0235(3) Uani 1 1 d . . .
N12 N 0.80539(13) 0.15336(15) 0.90254(12) 0.0210(4) Uani 1 1 d . . .
O12 O 0.65654(11) 0.34490(12) 0.88981(10) 0.0225(3) Uani 1 1 d . . .
C13 C 0.85919(15) 0.22204(18) 1.13177(15) 0.0200(4) Uani 1 1 d . . .
C15 C 0.71382(15) 0.39467(19) 1.11187(14) 0.0204(4) Uani 1 1 d . . .
N21 N 0.72369(15) -0.15680(18) 0.88952(14) 0.0298(4) Uani 1 1 d . . .
C14 C 0.76581(15) 0.28552(17) 1.07157(14) 0.0177(4) Uani 1 1 d . . .
C12 C 0.90009(17) 0.26719(19) 1.23040(15) 0.0217(4) Uani 1 1 d . . .
C11 C 0.84862(16) 0.37742(19) 1.27151(14) 0.0220(4) Uani 1 1 d . . .
N11 N 0.88887(17) 0.4212(2) 1.37001(13) 0.0320(4) Uani 1 1 d . . .
C16 C 0.75355(15) 0.43921(19) 1.21071(14) 0.0217(4) 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
S12 C19 1.719(2) . ?
S12 C17 1.7471(19) . ?
C17 N13 1.307(2) . ?
C17 N12 1.366(2) . ?
N13 C18 1.388(3) . ?
N22 C24 1.295(3) . ?
N22 C22 1.466(3) . ?
C24 N21 1.313(3) . ?
C24 C25 1.471(3) . ?
C22 C21 1.525(3) . ?
C18 C19 1.331(3) . ?
C21 N21 1.466(3) . ?
S11 O12 1.4576(13) . ?
S11 O11 1.4626(13) . ?
S11 N12 1.5641(16) . ?
S11 C14 1.7620(19) . ?
C13 C12 1.378(3) . ?
C13 C14 1.391(3) . ?
C15 C16 1.377(3) . ?
C15 C14 1.390(2) . ?
C12 C11 1.400(3) . ?
C11 N11 1.371(3) . ?
C11 C16 1.401(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
C19 S12 C17 89.53(10) . . ?
N13 C17 N12 129.74(17) . . ?
N13 C17 S12 113.80(14) . . ?
N12 C17 S12 116.44(13) . . ?
C17 N13 C18 109.94(16) . . ?
C24 N22 C22 111.69(17) . . ?
N22 C24 N21 112.18(19) . . ?
N22 C24 C25 123.34(19) . . ?
N21 C24 C25 124.48(19) . . ?
N22 C22 C21 102.42(16) . . ?
C19 C18 N13 117.15(19) . . ?
C18 C19 S12 109.57(17) . . ?
N21 C21 C22 102.76(16) . . ?
O12 S11 O11 112.85(8) . . ?
O12 S11 N12 116.09(8) . . ?
O11 S11 N12 105.03(8) . . ?
O12 S11 C14 106.09(8) . . ?
O11 S11 C14 106.99(8) . . ?
N12 S11 C14 109.48(9) . . ?
C17 N12 S11 120.69(12) . . ?
C12 C13 C14 120.34(18) . . ?
C16 C15 C14 120.52(17) . . ?
C24 N21 C21 110.91(17) . . ?
C15 C14 C13 119.40(17) . . ?
C15 C14 S11 119.88(14) . . ?
C13 C14 S11 120.68(14) . . ?
C13 C12 C11 120.69(18) . . ?
N11 C11 C12 120.52(18) . . ?
N11 C11 C16 120.98(18) . . ?
C12 C11 C16 118.48(17) . . ?
C15 C16 C11 120.55(17) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.257
_refine_diff_density_min   -0.336
_refine_diff_density_rms    0.052
