 
data_99scw127a
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H12 N4 O3 S'
_chemical_formula_weight          292.32
 
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           triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.451(2)
_cell_length_b                    11.797(2)
_cell_length_c                    14.488(3)
_cell_angle_alpha                 104.81(3)
_cell_angle_beta                  103.71(3)
_cell_angle_gamma                 98.48(3)
_cell_volume                      1322.9(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(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           0.2
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.2
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.468
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              608
_exptl_absorpt_coefficient_mu     0.258
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.950
_exptl_absorpt_correction_T_max   0.950
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature      293(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             11382
_diffrn_reflns_av_R_equivalents   0.0551
_diffrn_reflns_av_sigmaI/netI     0.0740
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          1.83
_diffrn_reflns_theta_max          25.02
_reflns_number_total              4612
_reflns_number_gt                 2969
_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)+(0.0630P)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          4612
_refine_ls_number_parameters      457
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0862
_refine_ls_R_factor_gt            0.0471
_refine_ls_wR_factor_ref          0.1255
_refine_ls_wR_factor_gt           0.1081
_refine_ls_goodness_of_fit_ref    0.970
_refine_ls_restrained_S_all       0.970
_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
S1 S 0.23896(9) 0.90913(6) 0.12174(6) 0.0468(2) Uani 1 1 d . . .
O1 O 0.1660(2) 0.79140(16) 0.12068(15) 0.0554(5) Uani 1 1 d . . .
O2 O 0.1352(2) 0.98698(18) 0.09408(16) 0.0591(6) Uani 1 1 d . . .
O3 O 0.7124(4) 1.3556(2) 0.5434(2) 0.1181(12) Uani 1 1 d . . .
N1 N 0.7243(3) 1.1608(2) 0.51793(19) 0.0510(7) Uani 1 1 d . . .
N2 N 0.3506(3) 0.8950(2) 0.04203(18) 0.0455(6) Uani 1 1 d . . .
N3 N 0.6009(3) 0.87514(18) 0.00968(17) 0.0434(6) Uani 1 1 d . . .
N4 N 0.6056(3) 0.67477(18) 0.07730(17) 0.0464(6) Uani 1 1 d . . .
C1 C 0.8893(5) 1.3102(4) 0.6749(3) 0.0670(10) Uani 1 1 d . . .
C2 C 0.7687(4) 1.2796(3) 0.5732(3) 0.0599(9) Uani 1 1 d . . .
C3 C 0.6089(4) 1.1062(2) 0.4248(2) 0.0448(7) Uani 1 1 d . . .
C4 C 0.5624(4) 0.9806(2) 0.3924(2) 0.0449(7) Uani 1 1 d . . .
C5 C 0.4488(4) 0.9198(3) 0.3009(2) 0.0465(7) Uani 1 1 d . . .
C6 C 0.3805(3) 0.9837(2) 0.2396(2) 0.0424(7) Uani 1 1 d . . .
C7 C 0.4248(4) 1.1084(3) 0.2722(3) 0.0559(9) Uani 1 1 d . . .
C8 C 0.5357(4) 1.1684(3) 0.3625(3) 0.0580(9) Uani 1 1 d . . .
C9 C 0.4792(3) 0.8323(2) 0.04375(19) 0.0371(6) Uani 1 1 d . . .
C10 C 0.7247(4) 0.8156(3) 0.0099(2) 0.0483(7) Uani 1 1 d . . .
C11 C 0.7279(4) 0.7188(2) 0.0442(2) 0.0497(7) Uani 1 1 d . . .
C12 C 0.4801(4) 0.7308(2) 0.0756(2) 0.0448(7) Uani 1 1 d . . .
S21 S 0.50845(8) 0.50786(5) -0.23770(5) 0.0427(2) Uani 1 1 d . . .
O21 O 0.5629(2) 0.62168(14) -0.25085(15) 0.0517(5) Uani 1 1 d . . .
O22 O 0.6287(2) 0.44614(15) -0.19839(15) 0.0522(5) Uani 1 1 d . . .
O23 O 0.0802(3) -0.00078(17) -0.60246(17) 0.0708(7) Uani 1 1 d . . .
N21 N 0.0506(3) 0.1808(2) -0.62031(19) 0.0498(6) Uani 1 1 d . . .
N22 N 0.3970(3) 0.5257(2) -0.15949(18) 0.0433(6) Uani 1 1 d . . .
N23 N 0.1601(3) 0.5464(2) -0.11254(18) 0.0512(6) Uani 1 1 d . . .
N24 N 0.0814(3) 0.6939(2) -0.2312(2) 0.0644(8) Uani 1 1 d . . .
C21 C -0.1122(6) 0.0029(4) -0.7497(3) 0.0682(10) Uani 1 1 d . . .
C22 C 0.0153(4) 0.0587(2) -0.6516(2) 0.0505(7) Uani 1 1 d . . .
C23 C 0.1611(3) 0.2565(2) -0.5290(2) 0.0438(7) Uani 1 1 d . . .
C24 C 0.2382(4) 0.3710(3) -0.5245(2) 0.0571(8) Uani 1 1 d . . .
C25 C 0.3434(4) 0.4482(3) -0.4358(2) 0.0550(8) Uani 1 1 d . . .
C26 C 0.3724(3) 0.4125(2) -0.3513(2) 0.0397(6) Uani 1 1 d . . .
C27 C 0.2950(4) 0.2987(2) -0.3555(2) 0.0458(7) Uani 1 1 d . . .
C28 C 0.1881(4) 0.2215(2) -0.4435(2) 0.0479(7) Uani 1 1 d . . .
C29 C 0.2569(3) 0.5751(2) -0.1676(2) 0.0419(7) Uani 1 1 d . . .
C210 C 0.0264(4) 0.5945(3) -0.1175(3) 0.0648(10) Uani 1 1 d . . .
C211 C -0.0145(5) 0.6646(3) -0.1758(3) 0.0693(10) Uani 1 1 d . . .
C212 C 0.2173(4) 0.6482(3) -0.2264(3) 0.0565(8) Uani 1 1 d . . .
H1A H 0.773(4) 1.115(3) 0.549(2) 0.064(10) Uiso 1 1 d . . .
H1B H 0.924(4) 1.243(3) 0.691(2) 0.079(11) Uiso 1 1 d . . .
H1C H 0.835(5) 1.344(3) 0.730(3) 0.124(15) Uiso 1 1 d . . .
H1D H 0.978(6) 1.377(4) 0.681(3) 0.127(16) Uiso 1 1 d . . .
H2A H 0.370(3) 0.958(2) 0.023(2) 0.054(9) Uiso 1 1 d . . .
H4 H 0.606(3) 0.936(2) 0.435(2) 0.047(7) Uiso 1 1 d . . .
H5 H 0.417(3) 0.840(2) 0.281(2) 0.048(8) Uiso 1 1 d . . .
H7 H 0.380(4) 1.148(2) 0.234(2) 0.061(9) Uiso 1 1 d . . .
H8 H 0.555(4) 1.253(3) 0.384(2) 0.069(9) Uiso 1 1 d . . .
H10 H 0.800(4) 0.850(2) -0.014(2) 0.056(9) Uiso 1 1 d . . .
H11 H 0.824(4) 0.683(2) 0.051(2) 0.062(9) Uiso 1 1 d . . .
H12 H 0.394(4) 0.698(2) 0.093(2) 0.057(9) Uiso 1 1 d . . .
H21A H 0.009(4) 0.214(3) -0.666(2) 0.063(10) Uiso 1 1 d . . .
H21B H -0.128(5) -0.072(4) -0.767(3) 0.114(17) Uiso 1 1 d . . .
H21C H -0.093(6) 0.028(4) -0.801(4) 0.135(19) Uiso 1 1 d . . .
H21D H -0.218(7) 0.019(4) -0.749(4) 0.15(2) Uiso 1 1 d . . .
H22A H 0.392(4) 0.469(3) -0.136(2) 0.068(11) Uiso 1 1 d . . .
H24 H 0.215(4) 0.391(2) -0.587(2) 0.061(9) Uiso 1 1 d . . .
H25 H 0.390(4) 0.525(3) -0.434(2) 0.074(10) Uiso 1 1 d . . .
H27 H 0.310(3) 0.275(2) -0.297(2) 0.056(8) Uiso 1 1 d . . .
H28 H 0.136(3) 0.146(2) -0.443(2) 0.064(9) Uiso 1 1 d . . .
H210 H -0.035(5) 0.571(3) -0.085(3) 0.088(14) Uiso 1 1 d . . .
H211 H -0.100(4) 0.701(3) -0.177(2) 0.078(11) Uiso 1 1 d . . .
H212 H 0.275(4) 0.669(3) -0.268(3) 0.081(12) 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
S1 O2 1.4257(19) . ?
S1 O1 1.4287(18) . ?
S1 N2 1.648(2) . ?
S1 C6 1.753(3) . ?
O3 C2 1.201(4) . ?
N1 C2 1.370(4) . ?
N1 C3 1.390(4) . ?
N2 C9 1.401(3) . ?
N3 C9 1.331(3) . ?
N3 C10 1.344(3) . ?
N4 C12 1.328(3) . ?
N4 C11 1.332(4) . ?
C1 C2 1.500(5) . ?
C3 C8 1.394(4) . ?
C3 C4 1.398(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.388(4) . ?
C7 C8 1.356(4) . ?
C9 C12 1.390(3) . ?
C10 C11 1.358(4) . ?
S21 O21 1.4286(17) . ?
S21 O22 1.4292(19) . ?
S21 N22 1.630(2) . ?
S21 C26 1.753(3) . ?
O23 C22 1.218(3) . ?
N21 C22 1.358(3) . ?
N21 C23 1.408(4) . ?
N22 C29 1.389(3) . ?
N23 C210 1.332(4) . ?
N23 C29 1.336(3) . ?
N24 C212 1.333(4) . ?
N24 C211 1.338(4) . ?
C21 C22 1.484(5) . ?
C23 C28 1.384(4) . ?
C23 C24 1.387(4) . ?
C24 C25 1.376(4) . ?
C25 C26 1.373(4) . ?
C26 C27 1.384(3) . ?
C27 C28 1.374(4) . ?
C29 C212 1.382(4) . ?
C210 C211 1.349(5) . ?
 
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
O2 S1 O1 120.22(12) . . ?
O2 S1 N2 103.87(12) . . ?
O1 S1 N2 108.08(12) . . ?
O2 S1 C6 109.05(13) . . ?
O1 S1 C6 108.54(13) . . ?
N2 S1 C6 106.18(13) . . ?
C2 N1 C3 128.7(3) . . ?
C9 N2 S1 124.97(19) . . ?
C9 N3 C10 115.9(2) . . ?
C12 N4 C11 116.6(2) . . ?
O3 C2 N1 122.4(3) . . ?
O3 C2 C1 121.2(3) . . ?
N1 C2 C1 116.3(3) . . ?
N1 C3 C8 124.4(2) . . ?
N1 C3 C4 117.5(2) . . ?
C8 C3 C4 118.1(3) . . ?
C5 C4 C3 121.0(3) . . ?
C4 C5 C6 119.7(3) . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 S1 120.9(2) . . ?
C7 C6 S1 119.7(2) . . ?
C8 C7 C6 121.0(3) . . ?
C7 C8 C3 120.8(3) . . ?
N3 C9 C12 121.5(2) . . ?
N3 C9 N2 115.0(2) . . ?
C12 C9 N2 123.5(3) . . ?
N3 C10 C11 122.4(3) . . ?
N4 C11 C10 121.9(3) . . ?
N4 C12 C9 121.6(3) . . ?
O21 S21 O22 119.89(12) . . ?
O21 S21 N22 108.51(12) . . ?
O22 S21 N22 103.98(12) . . ?
O21 S21 C26 108.25(13) . . ?
O22 S21 C26 109.41(12) . . ?
N22 S21 C26 105.92(12) . . ?
C22 N21 C23 126.7(3) . . ?
C29 N22 S21 126.7(2) . . ?
C210 N23 C29 115.5(3) . . ?
C212 N24 C211 116.1(3) . . ?
O23 C22 N21 123.0(3) . . ?
O23 C22 C21 122.4(3) . . ?
N21 C22 C21 114.6(3) . . ?
C28 C23 C24 119.6(3) . . ?
C28 C23 N21 121.6(3) . . ?
C24 C23 N21 118.8(3) . . ?
C25 C24 C23 120.1(3) . . ?
C26 C25 C24 120.2(3) . . ?
C25 C26 C27 119.8(3) . . ?
C25 C26 S21 121.3(2) . . ?
C27 C26 S21 118.9(2) . . ?
C28 C27 C26 120.4(3) . . ?
C27 C28 C23 119.8(3) . . ?
N23 C29 C212 121.4(3) . . ?
N23 C29 N22 114.2(3) . . ?
C212 C29 N22 124.4(3) . . ?
N23 C210 C211 123.5(4) . . ?
N24 C211 C210 121.5(3) . . ?
N24 C212 C29 122.0(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.990
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.990
_refine_diff_density_max    0.284
_refine_diff_density_min   -0.327
_refine_diff_density_rms    0.050
