 
data_s80
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C11 H6 N4 O3 S2 W'
_chemical_formula_weight          490.17
 
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'
 'S'  'S'   0.1246   0.1234
 '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'
 'W'  'W'  -0.8490   6.8722
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
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                    9.896(4)
_cell_length_b                    13.4790(15)
_cell_length_c                    11.6350(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  111.423(10)
_cell_angle_gamma                 90.00
_cell_volume                      1444.7(7)
_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        unk
_exptl_crystal_colour             unk
_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     2.254
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              920
_exptl_absorpt_coefficient_mu     8.298
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             5452
_diffrn_reflns_av_R_equivalents   0.1082
_diffrn_reflns_av_sigmaI/netI     0.1632
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.71
_diffrn_reflns_theta_max          24.71
_reflns_number_total              2424
_reflns_number_gt                 2006
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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 > 2σ(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)+(0.0825P)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     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2424
_refine_ls_number_parameters      166
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0832
_refine_ls_R_factor_gt            0.0778
_refine_ls_wR_factor_ref          0.2078
_refine_ls_wR_factor_gt           0.2017
_refine_ls_goodness_of_fit_ref    0.995
_refine_ls_restrained_S_all       0.995
_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
W1 W 0.19703(6) 0.18169(4) 0.26748(6) 0.0295(3) Uani 1 1 d . . .
S1 S 0.0316(5) 0.1482(3) 0.0477(4) 0.0432(10) Uani 1 1 d . . .
S2 S 0.2644(5) 0.1265(3) 0.4870(3) 0.0393(9) Uani 1 1 d . . .
O1 O 0.0300(14) 0.3837(9) 0.1913(15) 0.065(4) Uani 1 1 d . . .
O2 O 0.4334(18) 0.3409(11) 0.3974(18) 0.094(6) Uani 1 1 d . . .
O3 O 0.428(2) 0.1670(15) 0.145(3) 0.127(10) Uani 1 1 d . . .
N1 N -0.0184(7) 0.1277(6) 0.2449(6) 0.028(2) Uani 1 1 d G . .
C1 C -0.0783(8) 0.1164(6) 0.1174(6) 0.031(3) Uani 1 1 d G . .
N2 N -0.2204(9) 0.0832(7) 0.0614(6) 0.038(3) Uani 1 1 d G . .
C2 C -0.3025(7) 0.0614(7) 0.1328(8) 0.042(4) Uani 1 1 d G . .
H2 H -0.3976 0.0392 0.0953 0.051 Uiso 1 1 calc R . .
C3 C -0.2426(9) 0.0728(7) 0.2603(8) 0.044(4) Uani 1 1 d G . .
H3 H -0.2976 0.0582 0.3081 0.052 Uiso 1 1 calc R . .
C4 C -0.1005(9) 0.1059(7) 0.3163(5) 0.032(3) Uani 1 1 d G . .
H4 H -0.0605 0.1135 0.4016 0.039 Uiso 1 1 calc R . .
N3 N 0.2565(10) 0.0267(5) 0.3023(7) 0.030(3) Uani 1 1 d G . .
C5 C 0.2852(10) 0.0183(5) 0.4282(7) 0.028(3) Uani 1 1 d G . .
N4 N 0.3265(11) -0.0727(6) 0.4869(6) 0.045(3) Uani 1 1 d G . .
C6 C 0.3389(12) -0.1552(5) 0.4198(9) 0.052(5) Uani 1 1 d G . .
H6 H 0.3665 -0.2160 0.4591 0.063 Uiso 1 1 calc R . .
C7 C 0.3102(12) -0.1467(5) 0.2940(9) 0.044(4) Uani 1 1 d G . .
H7 H 0.3185 -0.2020 0.2491 0.053 Uiso 1 1 calc R . .
C8 C 0.2690(11) -0.0558(6) 0.2353(6) 0.035(3) Uani 1 1 d G . .
H8 H 0.2497 -0.0502 0.1511 0.042 Uiso 1 1 calc R . .
C9 C 0.0917(19) 0.3129(12) 0.2181(19) 0.046(5) Uani 1 1 d . . .
C10 C 0.3448(19) 0.2780(13) 0.3493(18) 0.056(5) Uani 1 1 d . . .
C11 C 0.349(2) 0.1785(13) 0.194(2) 0.061(7) Uani 1 1 d . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
W1 0.0333(5) 0.0126(4) 0.0388(5) 0.00503(18) 0.0087(3) -0.00080(19)
S1 0.048(2) 0.050(2) 0.033(2) 0.0094(19) 0.0180(18) -0.001(2)
S2 0.055(3) 0.0270(19) 0.030(2) -0.0099(14) 0.0079(17) 0.0029(16)
O1 0.048(8) 0.022(6) 0.116(12) 0.023(7) 0.017(7) 0.012(6)
O2 0.077(11) 0.037(7) 0.120(15) 0.003(9) -0.022(10) -0.029(8)
O3 0.070(12) 0.118(16) 0.23(3) 0.110(16) 0.093(16) 0.052(11)
N1 0.040(7) 0.008(5) 0.034(7) 0.003(4) 0.012(5) 0.002(4)
C1 0.042(9) 0.013(6) 0.033(8) 0.002(5) 0.008(6) 0.006(6)
N2 0.041(7) 0.029(7) 0.035(7) -0.007(5) 0.005(6) -0.006(6)
C2 0.035(9) 0.026(8) 0.066(12) -0.008(7) 0.019(8) 0.001(7)
C3 0.032(8) 0.035(9) 0.066(12) 0.016(8) 0.020(8) 0.001(7)
C4 0.051(9) 0.033(8) 0.018(7) 0.004(6) 0.018(6) 0.009(7)
N3 0.043(7) 0.014(5) 0.029(6) -0.001(5) 0.008(5) 0.001(5)
C5 0.035(8) 0.013(6) 0.036(8) 0.003(5) 0.012(6) 0.002(5)
N4 0.051(8) 0.031(7) 0.048(8) 0.012(6) 0.012(6) 0.003(6)
C6 0.051(11) 0.027(8) 0.075(14) 0.009(9) 0.018(9) 0.006(8)
C7 0.042(9) 0.033(9) 0.052(11) -0.012(8) 0.010(8) 0.007(7)
C8 0.045(9) 0.022(7) 0.039(9) -0.015(6) 0.016(7) 0.003(6)
C9 0.027(9) 0.038(10) 0.067(13) 0.004(7) 0.011(8) -0.014(7)
C10 0.041(10) 0.030(9) 0.072(12) 0.023(9) -0.007(8) 0.007(8)
C11 0.046(12) 0.044(12) 0.116(19) 0.042(10) 0.056(13) 0.018(8)
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
W1 C10 1.927(18) . ?
W1 C11 1.988(18) . ?
W1 C9 2.027(17) . ?
W1 N3 2.168(6) . ?
W1 N1 2.175(6) . ?
W1 S2 2.505(4) . ?
W1 S1 2.523(4) . ?
S1 C1 1.633(7) . ?
S2 C5 1.656(7) . ?
O1 C9 1.11(2) . ?
O2 C10 1.20(2) . ?
O3 C11 1.13(3) . ?
N1 C1 1.3900 . ?
N1 C4 1.3900 . ?
C1 N2 1.3900 . ?
N2 C2 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
N3 C5 1.3900 . ?
N3 C8 1.3900 . ?
C5 N4 1.3900 . ?
N4 C6 1.3900 . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 C8 1.3900 . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
 
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
C10 W1 C11 70.8(10) . . ?
C10 W1 C9 76.8(6) . . ?
C11 W1 C9 106.8(7) . . ?
C10 W1 N3 116.8(5) . . ?
C11 W1 N3 82.1(5) . . ?
C9 W1 N3 166.0(5) . . ?
C10 W1 N1 144.9(7) . . ?
C11 W1 N1 143.5(8) . . ?
C9 W1 N1 83.0(5) . . ?
N3 W1 N1 83.5(3) . . ?
C10 W1 S2 79.9(6) . . ?
C11 W1 S2 118.2(7) . . ?
C9 W1 S2 117.7(6) . . ?
N3 W1 S2 64.6(2) . . ?
N1 W1 S2 84.7(2) . . ?
C10 W1 S1 135.7(6) . . ?
C11 W1 S1 82.6(8) . . ?
C9 W1 S1 78.0(6) . . ?
N3 W1 S1 92.8(2) . . ?
N1 W1 S1 64.7(2) . . ?
S2 W1 S1 144.36(14) . . ?
C1 S1 W1 81.2(3) . . ?
C5 S2 W1 82.4(3) . . ?
C1 N1 C4 120.0 . . ?
C1 N1 W1 100.5(4) . . ?
C4 N1 W1 139.4(4) . . ?
N2 C1 N1 120.0 . . ?
N2 C1 S1 126.5(5) . . ?
N1 C1 S1 113.5(5) . . ?
C2 N2 C1 120.0 . . ?
C3 C2 N2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N2 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 N1 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C4 H4 120.0 . . ?
C5 N3 C8 120.0 . . ?
C5 N3 W1 102.3(4) . . ?
C8 N3 W1 137.7(4) . . ?
N4 C5 N3 120.0 . . ?
N4 C5 S2 129.2(5) . . ?
N3 C5 S2 110.8(5) . . ?
C5 N4 C6 120.0 . . ?
N4 C6 C7 120.0 . . ?
N4 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 N3 120.0 . . ?
C7 C8 H8 120.0 . . ?
N3 C8 H8 120.0 . . ?
O1 C9 W1 177.8(15) . . ?
O2 C10 W1 177.4(15) . . ?
O3 C11 W1 172(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.983
_diffrn_reflns_theta_full              24.71
_diffrn_measured_fraction_theta_full   0.983
_refine_diff_density_max    2.663
_refine_diff_density_min   -5.455
_refine_diff_density_rms    0.432
