 
data_2007may0016
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C6 H7 N O S'
_chemical_formula_weight          141.19
 
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                    10.0846(3)
_cell_length_b                    10.4718(3)
_cell_length_c                    10.9149(3)
_cell_angle_alpha                 106.7180(10)
_cell_angle_beta                  111.473(2)
_cell_angle_gamma                 95.603(2)
_cell_volume                      1000.33(5)
_cell_formula_units_Z             6
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     55607
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.06
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.406
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              444
_exptl_absorpt_coefficient_mu     0.394
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9767
_exptl_absorpt_correction_T_max   0.9922
_exptl_absorpt_process_details    
'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
The values of Tmin and Tmax are based on the cell
dimensions only and were generated using the size 
command in SHELX. SADABS reports the ratio of minimum 
to maximum apparent transmission as 0.815889
;
 
_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             20416
_diffrn_reflns_av_R_equivalents   0.0709
_diffrn_reflns_av_sigmaI/netI     0.0530
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          3.31
_diffrn_reflns_theta_max          27.50
_reflns_number_total              4571
_reflns_number_gt                 3522
_reflns_threshold_expression      >2sigma(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     '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)+(0.0983P)²+1.4846P] 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          4571
_refine_ls_number_parameters      271
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.0943
_refine_ls_R_factor_gt            0.0699
_refine_ls_wR_factor_ref          0.1960
_refine_ls_wR_factor_gt           0.1732
_refine_ls_goodness_of_fit_ref    1.126
_refine_ls_restrained_S_all       1.125
_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
C1 C 0.1537(4) 0.2535(3) 0.3445(3) 0.0232(7) Uani 1 1 d . . .
C2 C 0.2993(4) 0.3010(3) 0.4276(4) 0.0243(7) Uani 1 1 d . . .
H2 H 0.3728 0.2725 0.3982 0.029 Uiso 1 1 calc R . .
C3 C 0.3316(4) 0.3969(3) 0.5622(4) 0.0248(7) Uani 1 1 d . . .
C4 C 0.2066(4) 0.4183(4) 0.5774(4) 0.0292(7) Uani 1 1 d . . .
H4 H 0.2058 0.4794 0.6604 0.035 Uiso 1 1 calc R . .
C5 C 0.0889(4) 0.1522(3) 0.1994(3) 0.0229(7) Uani 1 1 d . . .
C6 C 0.4843(4) 0.4663(4) 0.6737(4) 0.0322(8) Uani 1 1 d . . .
H6A H 0.5175 0.5520 0.6632 0.048 Uiso 1 1 calc R . .
H6B H 0.5507 0.4057 0.6635 0.048 Uiso 1 1 calc R . .
H6C H 0.4838 0.4860 0.7669 0.048 Uiso 1 1 calc R . .
N1 N -0.0539(3) 0.1295(3) 0.1240(3) 0.0275(6) Uani 1 1 d D . .
O1 O 0.1700(3) 0.0914(2) 0.1525(3) 0.0271(5) Uani 1 1 d . . .
S1 S 0.05129(9) 0.32415(9) 0.43226(9) 0.0270(2) Uani 1 1 d . . .
C11 C 0.1674(4) 0.7481(3) 0.2977(4) 0.0231(7) Uani 1 1 d . . .
C12 C 0.0540(4) 0.7426(3) 0.1775(4) 0.0269(7) Uani 1 1 d . . .
H12 H 0.0500 0.8133 0.1386 0.032 Uiso 1 1 calc R . .
C13 C -0.0571(4) 0.6207(3) 0.1170(4) 0.0268(7) Uani 1 1 d . . .
C14 C -0.0223(4) 0.5373(4) 0.1942(4) 0.0301(8) Uani 1 1 d . . .
H14 H -0.0831 0.4507 0.1700 0.036 Uiso 1 1 calc R . .
C15 C 0.3039(4) 0.8535(3) 0.3907(3) 0.0240(7) Uani 1 1 d . . .
C16 C -0.1947(4) 0.5892(4) -0.0136(4) 0.0335(8) Uani 1 1 d . . .
H16A H -0.2206 0.4911 -0.0686 0.050 Uiso 1 1 calc R . .
H16B H -0.1788 0.6420 -0.0699 0.050 Uiso 1 1 calc R . .
H16C H -0.2744 0.6137 0.0126 0.050 Uiso 1 1 calc R . .
N2 N 0.3197(3) 0.9690(3) 0.3631(3) 0.0267(6) Uani 1 1 d D . .
O2 O 0.4002(3) 0.8341(2) 0.4898(3) 0.0284(5) Uani 1 1 d . . .
S2 S 0.14069(10) 0.60346(9) 0.33849(9) 0.0279(2) Uani 1 1 d . . .
H1N H -0.086(5) 0.069(4) 0.039(3) 0.038(12) Uiso 1 1 d D . .
H2N H -0.118(3) 0.160(4) 0.154(4) 0.018(9) Uiso 1 1 d D . .
H3N H 0.253(3) 0.979(4) 0.291(3) 0.027(10) Uiso 1 1 d D . .
H4N H 0.403(3) 1.028(4) 0.412(4) 0.038(12) Uiso 1 1 d D . .
H5N H 0.420(2) 0.136(4) 1.181(4) 0.030(11) Uiso 1 1 d D . .
H6N H 0.561(4) 0.170(4) 1.309(2) 0.020(9) Uiso 1 1 d D . .
C21 C 0.5011(4) 0.1747(3) 1.0008(4) 0.0248(7) Uani 1 1 d . . .
C22 C 0.3550(4) 0.1239(3) 0.9163(4) 0.0249(7) Uani 1 1 d . . .
H22 H 0.2857 0.0958 0.9488 0.030 Uiso 1 1 calc R . .
C23 C 0.3170(4) 0.1172(4) 0.7749(4) 0.0281(7) Uani 1 1 d . . .
C24 C 0.4376(4) 0.1641(4) 0.7577(4) 0.0329(8) Uani 1 1 d . . .
H24 H 0.4344 0.1681 0.6709 0.040 Uiso 1 1 calc R . .
C25 C 0.5873(4) 0.1950(3) 1.1502(4) 0.0243(7) Uani 1 1 d . . .
C26 C 0.1668(4) 0.0617(5) 0.6581(4) 0.0389(9) Uani 1 1 d . . .
H26A H 0.1670 0.0791 0.5746 0.058 Uiso 1 1 calc R . .
H26B H 0.0970 0.1067 0.6872 0.058 Uiso 1 1 calc R . .
H26C H 0.1381 -0.0372 0.6360 0.058 Uiso 1 1 calc R . .
N3 N 0.5138(3) 0.1696(3) 1.2232(3) 0.0265(6) Uani 1 1 d D . .
O3 O 0.7218(3) 0.2352(3) 1.2030(3) 0.0319(6) Uani 1 1 d . . .
S3 S 0.59544(10) 0.21520(11) 0.90858(10) 0.0364(3) 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
C1 C2 1.360(5) . ?
C1 C5 1.484(5) . ?
C1 S1 1.731(3) . ?
C2 C3 1.418(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.361(5) . ?
C3 C6 1.511(5) . ?
C4 S1 1.708(4) . ?
C4 H4 0.9500 . ?
C5 O1 1.249(4) . ?
C5 N1 1.326(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N1 H1N 0.874(19) . ?
N1 H2N 0.868(18) . ?
C11 C12 1.370(5) . ?
C11 C15 1.476(5) . ?
C11 S2 1.721(3) . ?
C12 C13 1.419(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(5) . ?
C13 C16 1.503(5) . ?
C14 S2 1.708(4) . ?
C14 H14 0.9500 . ?
C15 O2 1.245(4) . ?
C15 N2 1.337(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N2 H3N 0.870(19) . ?
N2 H4N 0.869(19) . ?
C21 C22 1.369(5) . ?
C21 C25 1.479(5) . ?
C21 S3 1.722(3) . ?
C22 C23 1.427(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.363(5) . ?
C23 C26 1.499(5) . ?
C24 S3 1.715(4) . ?
C24 H24 0.9500 . ?
C25 O3 1.235(4) . ?
C25 N3 1.330(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N3 H5N 0.872(19) . ?
N3 H6N 0.878(18) . ?
 
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
C2 C1 C5 125.4(3) . . ?
C2 C1 S1 110.9(2) . . ?
C5 C1 S1 123.7(2) . . ?
C1 C2 C3 113.8(3) . . ?
C1 C2 H2 123.1 . . ?
C3 C2 H2 123.1 . . ?
C4 C3 C2 111.0(3) . . ?
C4 C3 C6 124.6(3) . . ?
C2 C3 C6 124.5(3) . . ?
C3 C4 S1 113.2(3) . . ?
C3 C4 H4 123.4 . . ?
S1 C4 H4 123.4 . . ?
O1 C5 N1 122.3(3) . . ?
O1 C5 C1 119.1(3) . . ?
N1 C5 C1 118.6(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 N1 H1N 115(3) . . ?
C5 N1 H2N 127(2) . . ?
H1N N1 H2N 118(4) . . ?
C4 S1 C1 91.11(17) . . ?
C12 C11 C15 130.7(3) . . ?
C12 C11 S2 111.6(2) . . ?
C15 C11 S2 117.7(3) . . ?
C11 C12 C13 113.2(3) . . ?
C11 C12 H12 123.4 . . ?
C13 C12 H12 123.4 . . ?
C14 C13 C12 110.8(3) . . ?
C14 C13 C16 124.9(3) . . ?
C12 C13 C16 124.3(3) . . ?
C13 C14 S2 113.6(3) . . ?
C13 C14 H14 123.2 . . ?
S2 C14 H14 123.2 . . ?
O2 C15 N2 121.9(3) . . ?
O2 C15 C11 120.9(3) . . ?
N2 C15 C11 117.2(3) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 N2 H3N 120(3) . . ?
C15 N2 H4N 118(3) . . ?
H3N N2 H4N 122(4) . . ?
C14 S2 C11 90.87(17) . . ?
C22 C21 C25 131.5(3) . . ?
C22 C21 S3 111.2(3) . . ?
C25 C21 S3 117.2(2) . . ?
C21 C22 C23 113.5(3) . . ?
C21 C22 H22 123.3 . . ?
C23 C22 H22 123.3 . . ?
C24 C23 C22 110.8(3) . . ?
C24 C23 C26 123.7(3) . . ?
C22 C23 C26 125.4(3) . . ?
C23 C24 S3 113.3(3) . . ?
C23 C24 H24 123.4 . . ?
S3 C24 H24 123.4 . . ?
O3 C25 N3 122.6(3) . . ?
O3 C25 C21 120.2(3) . . ?
N3 C25 C21 117.3(3) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 N3 H5N 120(3) . . ?
C25 N3 H6N 120(3) . . ?
H5N N3 H6N 119(4) . . ?
C24 S3 C21 91.25(18) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N1 H1N O1  0.874(19) 2.08(2) 2.949(4) 173(4) 2
N1 H2N O3  0.868(18) 2.04(2) 2.908(4) 174(3) 1_454
N2 H3N O1  0.870(19) 2.16(3) 2.956(4) 152(4) 1_565
N2 H4N O2  0.869(19) 2.04(2) 2.906(4) 175(4) 2_676
N3 H5N O1  0.872(19) 2.40(2) 3.227(4) 158(4) 1_556
N3 H6N O2  0.878(18) 2.10(2) 2.942(4) 160(3) 2_667
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.897
_refine_diff_density_min   -0.595
_refine_diff_density_rms    0.127
