 
data_2008src1291p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H15 N3 O2 S'
_chemical_formula_weight          241.31
 
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/c
 
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                    20.4469(13)
_cell_length_b                    5.6971(3)
_cell_length_c                    9.6808(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  93.743(4)
_cell_angle_gamma                 90.00
_cell_volume                      1125.29(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     17440
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        lath
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.23
_exptl_crystal_size_mid           0.03
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.424
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              512
_exptl_absorpt_coefficient_mu     0.277
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9390
_exptl_absorpt_correction_T_max   0.9972
_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             8885
_diffrn_reflns_av_R_equivalents   0.1029
_diffrn_reflns_av_sigmaI/netI     0.0894
_diffrn_reflns_limit_h_min        -24
_diffrn_reflns_limit_h_max        24
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          3.00
_diffrn_reflns_theta_max          25.02
_reflns_number_total              1981
_reflns_number_gt                 1289
_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.

 Due to the weakly diffracting nature of the crystals, data were only
 included out to 25deg (ACTA 50).
;
 
_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)+(0.0000P)²+6.1699P] 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          1981
_refine_ls_number_parameters      146
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1461
_refine_ls_R_factor_gt            0.0876
_refine_ls_wR_factor_ref          0.1760
_refine_ls_wR_factor_gt           0.1490
_refine_ls_goodness_of_fit_ref    1.143
_refine_ls_restrained_S_all       1.143
_refine_ls_shift/su_max           0.012
_refine_ls_shift/su_mean          0.002
 
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 0.1045(3) 0.3398(12) -0.1517(6) 0.0335(16) Uani 1 1 d . . .
H2 H 0.1001 0.2143 -0.2163 0.040 Uiso 1 1 calc R . .
C3 C 0.0557(3) 0.5076(13) -0.1562(6) 0.0316(14) Uani 1 1 d . . .
H3 H 0.0189 0.4991 -0.2212 0.038 Uiso 1 1 calc R . .
C4 C 0.0630(3) 0.6884(12) -0.0615(6) 0.0354(16) Uani 1 1 d . . .
H4 H 0.0303 0.8066 -0.0598 0.042 Uiso 1 1 calc R . .
C5 C 0.1173(3) 0.6995(11) 0.0306(6) 0.0265(14) Uani 1 1 d . . .
H5 H 0.1227 0.8258 0.0944 0.032 Uiso 1 1 calc R . .
C6 C 0.1642(2) 0.5214(10) 0.0284(5) 0.0191(12) Uani 1 1 d . . .
C8 C 0.2227(3) 0.6505(10) 0.2462(5) 0.0201(13) Uani 1 1 d . . .
H8A H 0.2031 0.5501 0.3159 0.024 Uiso 1 1 calc R . .
H8B H 0.1959 0.7947 0.2348 0.024 Uiso 1 1 calc R . .
C9 C 0.2917(3) 0.7155(10) 0.2970(6) 0.0233(13) Uani 1 1 d . . .
H9A H 0.3105 0.8271 0.2320 0.028 Uiso 1 1 calc R . .
H9B H 0.2916 0.7913 0.3890 0.028 Uiso 1 1 calc R . .
C11 C 0.3324(3) 0.3807(10) 0.1702(5) 0.0212(13) Uani 1 1 d . . .
H11A H 0.3597 0.2373 0.1781 0.025 Uiso 1 1 calc R . .
H11B H 0.3516 0.4876 0.1030 0.025 Uiso 1 1 calc R . .
C12 C 0.2635(3) 0.3174(10) 0.1202(6) 0.0235(13) Uani 1 1 d . . .
H12A H 0.2637 0.2455 0.0271 0.028 Uiso 1 1 calc R . .
H12B H 0.2459 0.2007 0.1837 0.028 Uiso 1 1 calc R . .
C15 C 0.4529(3) 0.7063(10) 0.3214(6) 0.0246(14) Uani 1 1 d . . .
H15A H 0.4962 0.7044 0.3713 0.037 Uiso 1 1 calc R . .
H15B H 0.4346 0.8650 0.3237 0.037 Uiso 1 1 calc R . .
H15C H 0.4571 0.6588 0.2251 0.037 Uiso 1 1 calc R . .
N1 N 0.1579(2) 0.3413(9) -0.0621(5) 0.0291(12) Uani 1 1 d . . .
N7 N 0.2217(2) 0.5251(8) 0.1139(4) 0.0202(10) Uani 1 1 d . . .
N10 N 0.33163(19) 0.4969(9) 0.3065(4) 0.0175(10) Uani 1 1 d . . .
O13 O 0.42863(18) 0.2792(7) 0.3991(4) 0.0237(9) Uani 1 1 d . . .
O14 O 0.38620(18) 0.6092(7) 0.5315(3) 0.0232(9) Uani 1 1 d . . .
S1 S 0.40063(7) 0.5098(3) 0.40080(13) 0.0199(4) 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
C2 0.029(4) 0.038(4) 0.033(3) -0.009(3) -0.002(3) -0.006(3)
C3 0.025(3) 0.042(4) 0.027(3) -0.001(3) -0.005(2) -0.007(4)
C4 0.031(4) 0.042(4) 0.032(3) 0.006(3) -0.003(3) 0.009(3)
C5 0.028(3) 0.031(4) 0.020(3) -0.005(3) -0.001(3) 0.007(3)
C6 0.018(3) 0.020(3) 0.020(3) 0.005(3) 0.006(2) -0.005(3)
C8 0.020(3) 0.017(3) 0.023(3) -0.001(2) 0.001(2) 0.003(2)
C9 0.029(3) 0.019(3) 0.021(3) -0.003(2) -0.002(2) 0.003(3)
C11 0.025(3) 0.022(3) 0.016(3) -0.003(2) -0.001(2) 0.007(3)
C12 0.028(3) 0.017(3) 0.025(3) -0.007(3) -0.005(2) 0.002(3)
C15 0.017(3) 0.028(3) 0.028(3) 0.007(3) -0.001(2) -0.001(3)
N1 0.030(3) 0.029(3) 0.028(3) -0.003(2) -0.002(2) -0.003(2)
N7 0.018(2) 0.018(3) 0.024(2) -0.001(2) -0.0017(19) 0.006(2)
N10 0.017(2) 0.020(2) 0.016(2) 0.000(2) 0.0031(17) 0.001(2)
O13 0.027(2) 0.017(2) 0.026(2) 0.0013(17) -0.0006(17) 0.0026(18)
O14 0.030(2) 0.022(2) 0.0168(18) 0.0004(17) -0.0006(16) 0.0005(18)
S1 0.0230(7) 0.0192(7) 0.0175(6) 0.0002(7) 0.0010(5) 0.0000(7)
 
_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 1.349(7) . ?
C2 C3 1.380(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(8) . ?
C5 H5 0.9500 . ?
C6 N1 1.350(7) . ?
C6 N7 1.394(6) . ?
C8 N7 1.465(7) . ?
C8 C9 1.510(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N10 1.489(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 N10 1.478(6) . ?
C11 C12 1.503(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N7 1.459(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 S1 1.759(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N10 S1 1.631(4) . ?
O13 S1 1.434(4) . ?
O14 S1 1.435(4) . ?
 
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 124.7(6) . . ?
N1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 C4 116.7(5) . . ?
C2 C3 H3 121.7 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.7(6) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
N1 C6 N7 116.1(5) . . ?
N1 C6 C5 121.7(5) . . ?
N7 C6 C5 122.2(5) . . ?
N7 C8 C9 111.3(4) . . ?
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 108.2(4) . . ?
N10 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
N10 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
N10 C11 C12 109.3(4) . . ?
N10 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
N10 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
N7 C12 C11 110.7(5) . . ?
N7 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
N7 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 N1 C2 117.5(5) . . ?
C6 N7 C12 118.8(5) . . ?
C6 N7 C8 119.3(4) . . ?
C12 N7 C8 112.6(4) . . ?
C11 N10 C9 110.9(4) . . ?
C11 N10 S1 117.4(3) . . ?
C9 N10 S1 116.6(4) . . ?
O13 S1 O14 118.5(2) . . ?
O13 S1 N10 106.5(2) . . ?
O14 S1 N10 106.9(2) . . ?
O13 S1 C15 108.9(3) . . ?
O14 S1 C15 107.4(3) . . ?
N10 S1 C15 108.2(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.394
_refine_diff_density_min   -0.402
_refine_diff_density_rms    0.096
