 
data_2009src0461p-1
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H5 N3 O S'
_chemical_formula_weight          191.21
 
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'
 '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'
 'H'  'H'   0.0000   0.0000
 '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                    6.1693(5)
_cell_length_b                    7.0845(6)
_cell_length_c                    10.3537(8)
_cell_angle_alpha                 87.871(5)
_cell_angle_beta                  74.394(5)
_cell_angle_gamma                 69.471(5)
_cell_volume                      407.34(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     15253
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.11
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.559
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              196
_exptl_absorpt_coefficient_mu     0.353
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9622
_exptl_absorpt_correction_T_max   0.9965
_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             6867
_diffrn_reflns_av_R_equivalents   0.0607
_diffrn_reflns_av_sigmaI/netI     0.0594
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.08
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1849
_reflns_number_gt                 1358
_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.

 Thiophene ring is disordered: 38.27% of the time in position b. EADP
 restraints used on thiophene ring, together with SAME command.
;
 
_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+0.7389P] 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          1849
_refine_ls_number_parameters      142
_refine_ls_number_restraints      10
_refine_ls_R_factor_all           0.0970
_refine_ls_R_factor_gt            0.0642
_refine_ls_wR_factor_ref          0.1271
_refine_ls_wR_factor_gt           0.1118
_refine_ls_goodness_of_fit_ref    1.129
_refine_ls_restrained_S_all       1.127
_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
C1 C 1.153(3) 0.205(3) -0.1002(11) 0.0248(13) Uani 0.617(4) 1 d PD A 1
C2 C 1.065(2) 0.196(2) -0.2130(11) 0.0248(13) Uani 0.617(4) 1 d PD A 1
H2 H 0.9025 0.2173 -0.2093 0.030 Uiso 0.617(4) 1 calc PR A 1
C3 C 1.476(3) 0.1253(15) -0.3070(9) 0.0248(13) Uani 0.617(4) 1 d PD A 1
H3 H 1.6262 0.0916 -0.3733 0.030 Uiso 0.617(4) 1 calc PR A 1
C4 C 1.2642(13) 0.1494(14) -0.3349(11) 0.0248(13) Uani 0.617(4) 1 d PD A 1
H4 H 1.2485 0.1374 -0.4227 0.030 Uiso 0.617(4) 1 calc PR A 1
S1 S 1.4400(4) 0.1625(5) -0.1388(3) 0.0247(5) Uani 0.617(4) 1 d PD A 1
C1B C 1.131(3) 0.208(4) -0.1064(14) 0.012(3) Uani 0.383(4) 1 d PD A 2
C2B C 1.387(3) 0.165(3) -0.1390(19) 0.027(2) Uani 0.383(4) 1 d PD A 2
H2B H 1.4767 0.1584 -0.0761 0.032 Uiso 0.383(4) 1 calc PR A 2
C3B C 1.310(2) 0.150(2) -0.3475(18) 0.027(2) Uani 0.383(4) 1 d PD A 2
H3B H 1.3387 0.1307 -0.4418 0.032 Uiso 0.383(4) 1 calc PR A 2
C4B C 1.486(4) 0.135(3) -0.2852(14) 0.027(2) Uani 0.383(4) 1 d PD A 2
H4B H 1.6502 0.1079 -0.3312 0.032 Uiso 0.383(4) 1 calc PR A 2
S1B S 1.0352(8) 0.2057(7) -0.2359(4) 0.0244(8) Uani 0.383(4) 1 d PD A 2
C8 C 0.6560(5) 0.3316(4) 0.1918(3) 0.0215(6) Uani 1 1 d . A .
C5 C 0.9955(5) 0.2558(4) 0.0337(3) 0.0209(6) Uani 1 1 d . . .
C10 C 0.8275(5) 0.3527(4) 0.3810(3) 0.0236(6) Uani 1 1 d . A .
C7 C 0.8397(5) 0.3271(4) 0.2446(3) 0.0214(6) Uani 1 1 d . . .
N11 N 0.8171(5) 0.3715(4) 0.4932(3) 0.0316(6) Uani 1 1 d . . .
N12 N 0.4220(5) 0.3734(4) 0.2423(3) 0.0280(6) Uani 1 1 d . . .
N6 N 1.0541(4) 0.2797(4) 0.1406(2) 0.0212(5) Uani 1 1 d . A .
O9 O 0.7525(3) 0.2861(3) 0.05686(19) 0.0226(5) Uani 1 1 d . A .
H12B H 0.336(6) 0.348(5) 0.195(3) 0.031(9) Uiso 1 1 d . . .
H12A H 0.348(8) 0.432(7) 0.326(5) 0.062(13) Uiso 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
C1 0.031(3) 0.026(2) 0.018(2) -0.0023(16) -0.0070(17) -0.0091(18)
C2 0.031(3) 0.026(2) 0.018(2) -0.0023(16) -0.0070(17) -0.0091(18)
C3 0.031(3) 0.026(2) 0.018(2) -0.0023(16) -0.0070(17) -0.0091(18)
C4 0.031(3) 0.026(2) 0.018(2) -0.0023(16) -0.0070(17) -0.0091(18)
S1 0.0172(9) 0.0328(9) 0.0218(8) -0.0013(6) -0.0016(7) -0.0085(8)
C1B 0.006(4) 0.010(4) 0.022(5) 0.004(4) -0.007(3) -0.001(4)
C2B 0.021(4) 0.034(4) 0.023(4) 0.001(3) 0.004(3) -0.013(3)
C3B 0.021(4) 0.034(4) 0.023(4) 0.001(3) 0.004(3) -0.013(3)
C4B 0.021(4) 0.034(4) 0.023(4) 0.001(3) 0.004(3) -0.013(3)
S1B 0.0267(16) 0.0300(14) 0.0175(16) -0.0013(12) -0.0067(10) -0.0106(11)
C8 0.0224(14) 0.0216(15) 0.0193(14) -0.0005(11) -0.0026(11) -0.0084(12)
C5 0.0211(14) 0.0187(14) 0.0234(14) 0.0004(11) -0.0075(12) -0.0063(12)
C10 0.0191(14) 0.0278(16) 0.0238(15) 0.0018(12) -0.0058(12) -0.0085(12)
C7 0.0189(14) 0.0242(15) 0.0208(14) 0.0002(11) -0.0039(11) -0.0083(12)
N11 0.0262(14) 0.0465(17) 0.0223(14) 0.0009(12) -0.0044(11) -0.0148(12)
N12 0.0198(13) 0.0390(16) 0.0253(14) -0.0078(12) -0.0039(11) -0.0113(12)
N6 0.0224(12) 0.0225(13) 0.0180(12) -0.0007(10) -0.0044(10) -0.0078(10)
O9 0.0216(10) 0.0278(11) 0.0191(10) -0.0017(8) -0.0068(8) -0.0085(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
C1 C2 1.425(17) . ?
C1 C5 1.435(9) . ?
C1 S1 1.627(16) . ?
C2 C4 1.458(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(8) . ?
C3 S1 1.713(7) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C1B C2B 1.45(2) . ?
C1B C5 1.449(13) . ?
C1B S1B 1.607(18) . ?
C2B C4B 1.464(17) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.379(12) . ?
C3B S1B 1.694(11) . ?
C3B H3B 0.9500 . ?
C4B H4B 0.9500 . ?
C8 N12 1.323(4) . ?
C8 O9 1.365(3) . ?
C8 C7 1.375(4) . ?
C5 N6 1.287(4) . ?
C5 O9 1.391(3) . ?
C10 N11 1.156(4) . ?
C10 C7 1.409(4) . ?
C7 N6 1.403(4) . ?
N12 H12B 0.87(4) . ?
N12 H12A 0.90(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
C2 C1 C5 121.9(12) . . ?
C2 C1 S1 113.9(8) . . ?
C5 C1 S1 124.1(11) . . ?
C1 C2 C4 109.1(11) . . ?
C1 C2 H2 125.4 . . ?
C4 C2 H2 125.4 . . ?
C4 C3 S1 112.3(12) . . ?
C4 C3 H3 123.8 . . ?
S1 C3 H3 123.8 . . ?
C3 C4 C2 111.5(13) . . ?
C3 C4 H4 124.2 . . ?
C2 C4 H4 124.2 . . ?
C1 S1 C3 93.1(7) . . ?
C2B C1B C5 117.4(15) . . ?
C2B C1B S1B 113.4(10) . . ?
C5 C1B S1B 129.2(11) . . ?
C1B C2B C4B 108.6(16) . . ?
C1B C2B H2B 125.7 . . ?
C4B C2B H2B 125.7 . . ?
C4B C3B S1B 112.0(18) . . ?
C4B C3B H3B 124.0 . . ?
S1B C3B H3B 124.0 . . ?
C3B C4B C2B 111(2) . . ?
C3B C4B H4B 124.4 . . ?
C2B C4B H4B 124.4 . . ?
C1B S1B C3B 94.7(8) . . ?
N12 C8 O9 118.3(3) . . ?
N12 C8 C7 134.5(3) . . ?
O9 C8 C7 107.2(2) . . ?
N6 C5 O9 113.5(2) . . ?
N6 C5 C1 126.7(8) . . ?
O9 C5 C1 119.8(8) . . ?
N6 C5 C1B 132.9(8) . . ?
O9 C5 C1B 113.6(8) . . ?
C1 C5 C1B 6.3(15) . . ?
N11 C10 C7 179.2(3) . . ?
C8 C7 N6 109.2(2) . . ?
C8 C7 C10 127.3(3) . . ?
N6 C7 C10 123.4(2) . . ?
C8 N12 H12B 121(2) . . ?
C8 N12 H12A 120(3) . . ?
H12B N12 H12A 119(3) . . ?
C5 N6 C7 105.0(2) . . ?
C8 O9 C5 105.1(2) . . ?
 
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
N12 H12B N6  0.87(4) 2.18(4) 3.016(4) 162(3) 1_455
N12 H12A N11  0.90(5) 2.16(5) 3.044(4) 168(4) 2_666
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.306
_refine_diff_density_min   -0.358
_refine_diff_density_rms    0.074
