 
data_2009src0064
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H14 N4 O S'
_chemical_formula_weight          274.34
 
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
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    6.2194(2)
_cell_length_b                    7.6717(2)
_cell_length_c                    13.7114(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  101.551(2)
_cell_angle_gamma                 90.00
_cell_volume                      640.97(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     28753
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.421
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              288
_exptl_absorpt_coefficient_mu     0.250
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9754
_exptl_absorpt_correction_T_max   0.9925
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)'

 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             7626
_diffrn_reflns_av_R_equivalents   0.0345
_diffrn_reflns_av_sigmaI/netI     0.0432
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.03
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2712
_reflns_number_gt                 2523
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.0243P)²+0.2721P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.14(8)
_refine_ls_number_reflns          2712
_refine_ls_number_parameters      172
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0419
_refine_ls_R_factor_gt            0.0375
_refine_ls_wR_factor_ref          0.0833
_refine_ls_wR_factor_gt           0.0804
_refine_ls_goodness_of_fit_ref    1.082
_refine_ls_restrained_S_all       1.082
_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
C2 C 0.8314(4) 0.6609(3) 0.74870(19) 0.0322(6) Uani 1 1 d . . .
H2 H 0.7562 0.5972 0.7910 0.039 Uiso 1 1 calc R . .
C3 C 1.0467(4) 0.7089(3) 0.78523(17) 0.0300(5) Uani 1 1 d . . .
H3 H 1.1203 0.6808 0.8509 0.036 Uiso 1 1 calc R . .
C4 C 1.1481(4) 0.8003(3) 0.72034(17) 0.0272(5) Uani 1 1 d . . .
H4 H 1.2964 0.8350 0.7425 0.033 Uiso 1 1 calc R . .
C6 C 0.8376(4) 0.7898(3) 0.59989(16) 0.0213(4) Uani 1 1 d . . .
C8 C 0.8431(3) 0.9133(3) 0.43358(15) 0.0231(5) Uani 1 1 d . . .
H8A H 0.9914 0.9516 0.4673 0.028 Uiso 1 1 calc R . .
H8B H 0.7613 1.0172 0.4034 0.028 Uiso 1 1 calc R . .
C9 C 0.8630(3) 0.7830(3) 0.35216(15) 0.0192(4) Uani 1 1 d . . .
H9A H 0.9256 0.8414 0.2998 0.023 Uiso 1 1 calc R . .
H9B H 0.9631 0.6874 0.3805 0.023 Uiso 1 1 calc R . .
C11 C 0.5335(4) 0.6352(3) 0.38294(16) 0.0200(4) Uani 1 1 d . . .
H11A H 0.6173 0.5333 0.4145 0.024 Uiso 1 1 calc R . .
H11B H 0.3856 0.5946 0.3500 0.024 Uiso 1 1 calc R . .
C12 C 0.5128(3) 0.7697(3) 0.46217(16) 0.0223(5) Uani 1 1 d . . .
H12A H 0.4172 0.8666 0.4318 0.027 Uiso 1 1 calc R . .
H12B H 0.4450 0.7154 0.5142 0.027 Uiso 1 1 calc R . .
C13 C 0.5263(3) 0.7465(3) 0.21697(16) 0.0191(4) Uani 1 1 d . . .
C14 C 0.6414(3) 0.8023(3) 0.13758(15) 0.0196(4) Uani 1 1 d . . .
C15 C 0.8404(3) 0.7551(3) 0.11815(16) 0.0220(5) Uani 1 1 d . . .
H15 H 0.9398 0.6790 0.1594 0.026 Uiso 1 1 calc R . .
C16 C 0.8829(4) 0.8319(3) 0.02971(16) 0.0252(5) Uani 1 1 d . . .
H16 H 1.0137 0.8131 0.0054 0.030 Uiso 1 1 calc R . .
C17 C 0.7158(3) 0.9350(4) -0.01628(15) 0.0271(5) Uani 1 1 d . . .
H17 H 0.7169 0.9977 -0.0759 0.032 Uiso 1 1 calc R . .
N1 N 0.7236(3) 0.6996(3) 0.65661(14) 0.0280(4) Uani 1 1 d . . .
N5 N 1.0480(3) 0.8422(3) 0.62812(14) 0.0245(4) Uani 1 1 d . . .
N7 N 0.7295(3) 0.8368(2) 0.50676(13) 0.0226(4) Uani 1 1 d . . .
N10 N 0.6459(3) 0.7113(2) 0.30846(13) 0.0199(4) Uani 1 1 d . . .
O19 O 0.3253(2) 0.7247(2) 0.19643(12) 0.0288(4) Uani 1 1 d . . .
S18 S 0.50252(8) 0.93889(8) 0.04575(4) 0.02609(14) Uani 1 1 d . . .
 
 
_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
C2 N1 1.339(3) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 N5 1.332(3) . ?
C4 H4 0.9500 . ?
C6 N1 1.345(3) . ?
C6 N5 1.349(3) . ?
C6 N7 1.367(3) . ?
C8 N7 1.461(3) . ?
C8 C9 1.522(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N10 1.470(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 N10 1.469(3) . ?
C11 C12 1.522(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N7 1.458(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O19 1.237(2) . ?
C13 N10 1.351(3) . ?
C13 C14 1.481(3) . ?
C14 C15 1.366(3) . ?
C14 S18 1.730(2) . ?
C15 C16 1.420(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.357(3) . ?
C16 H16 0.9500 . ?
C17 S18 1.713(2) . ?
C17 H17 0.9500 . ?
 
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
N1 C2 C3 123.3(2) . . ?
N1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C4 C3 C2 115.9(2) . . ?
C4 C3 H3 122.1 . . ?
C2 C3 H3 122.1 . . ?
N5 C4 C3 123.2(2) . . ?
N5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
N1 C6 N5 125.5(2) . . ?
N1 C6 N7 117.29(19) . . ?
N5 C6 N7 117.17(19) . . ?
N7 C8 C9 111.17(17) . . ?
N7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N10 C9 C8 110.00(17) . . ?
N10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N10 C11 C12 110.30(17) . . ?
N10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
N10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N7 C12 C11 109.59(17) . . ?
N7 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
N7 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
O19 C13 N10 121.9(2) . . ?
O19 C13 C14 119.15(19) . . ?
N10 C13 C14 118.88(17) . . ?
C15 C14 C13 131.1(2) . . ?
C15 C14 S18 111.00(17) . . ?
C13 C14 S18 117.75(15) . . ?
C14 C15 C16 112.8(2) . . ?
C14 C15 H15 123.6 . . ?
C16 C15 H15 123.6 . . ?
C17 C16 C15 112.51(19) . . ?
C17 C16 H16 123.7 . . ?
C15 C16 H16 123.7 . . ?
C16 C17 S18 112.12(17) . . ?
C16 C17 H17 123.9 . . ?
S18 C17 H17 123.9 . . ?
C2 N1 C6 115.9(2) . . ?
C4 N5 C6 116.3(2) . . ?
C6 N7 C12 122.62(18) . . ?
C6 N7 C8 122.20(17) . . ?
C12 N7 C8 112.79(17) . . ?
C13 N10 C11 118.33(17) . . ?
C13 N10 C9 126.39(17) . . ?
C11 N10 C9 113.05(16) . . ?
C17 S18 C14 91.57(11) . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.184
_refine_diff_density_min   -0.206
_refine_diff_density_rms    0.050
