Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008231/cv6111sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008231/cv6111Isup2.hkl |
CCDC reference: 189385
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
C13H12N2OS2 | Dx = 1.450 Mg m−3 |
Mr = 276.37 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4198 reflections |
a = 5.1608 (1) Å | θ = 2.7–28.3° |
b = 9.4909 (2) Å | µ = 0.41 mm−1 |
c = 25.8492 (7) Å | T = 293 K |
V = 1266.11 (5) Å3 | Slab, yellow |
Z = 4 | 0.50 × 0.36 × 0.18 mm |
F(000) = 576 |
Siemens SMART CCD area-detector diffractometer | 1819 independent reflections |
Radiation source: fine-focus sealed tube | 1354 reflections with I > \2s(I) |
Graphite monochromator | Rint = 0.098 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.4°, θmin = 2.7° |
ω scans | h = −6→6 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −12→9 |
Tmin = 0.822, Tmax = 0.930 | l = −29→34 |
7639 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0835P)2] where P = (Fo2 + 2Fc2)/3 |
1819 reflections | (Δ/σ)max < 0.001 |
168 parameters | Δρmax = 1.14 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. 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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.4589 (3) | 0.10790 (15) | 0.15175 (5) | 0.0353 (4) | |
S2 | 0.2867 (3) | 0.08316 (15) | 0.04029 (5) | 0.0399 (4) | |
O1 | 0.9665 (10) | 0.3408 (5) | 0.21024 (14) | 0.0477 (12) | |
N1 | 0.8086 (9) | 0.3032 (4) | 0.11433 (14) | 0.0286 (9) | |
N2 | 0.6577 (9) | 0.2463 (4) | 0.07616 (15) | 0.0346 (11) | |
H2A | 0.6818 | 0.2728 | 0.0447 | 0.042* | |
C1 | 1.1388 (11) | 0.4315 (5) | 0.1896 (2) | 0.0345 (13) | |
C2 | 1.2990 (13) | 0.5013 (7) | 0.2248 (2) | 0.0454 (16) | |
H2 | 1.2800 | 0.4839 | 0.2600 | 0.055* | |
C3 | 1.4819 (13) | 0.5940 (7) | 0.20861 (19) | 0.0458 (15) | |
H3 | 1.5874 | 0.6384 | 0.2328 | 0.055* | |
C4 | 1.5143 (11) | 0.6241 (5) | 0.1550 (2) | 0.0321 (11) | |
C5 | 1.7074 (12) | 0.7214 (6) | 0.1381 (2) | 0.0378 (13) | |
H5 | 1.8172 | 0.7634 | 0.1621 | 0.045* | |
C6 | 1.7311 (11) | 0.7528 (6) | 0.0873 (2) | 0.0379 (13) | |
H6 | 1.8545 | 0.8179 | 0.0765 | 0.045* | |
C7 | 1.5688 (12) | 0.6868 (7) | 0.0507 (2) | 0.0439 (15) | |
H7 | 1.5882 | 0.7072 | 0.0157 | 0.053* | |
C8 | 1.3837 (10) | 0.5933 (6) | 0.06616 (18) | 0.0328 (12) | |
H8 | 1.2781 | 0.5516 | 0.0414 | 0.039* | |
C9 | 1.3480 (10) | 0.5580 (5) | 0.11881 (19) | 0.0278 (11) | |
C10 | 1.1568 (10) | 0.4598 (5) | 0.13679 (18) | 0.0265 (11) | |
C11 | 0.9841 (10) | 0.3911 (5) | 0.10023 (18) | 0.0293 (11) | |
H11 | 1.0014 | 0.4116 | 0.0652 | 0.035* | |
C12 | 0.4755 (11) | 0.1517 (5) | 0.08604 (17) | 0.0269 (11) | |
C13 | 0.2061 (12) | −0.0206 (6) | 0.1536 (2) | 0.0445 (15) | |
H13C | 0.0419 | 0.0250 | 0.1487 | 0.053* | |
H13A | 0.2075 | −0.0672 | 0.1866 | 0.053* | |
H13B | 0.2330 | −0.0885 | 0.1266 | 0.053* | |
H1A | 0.891 (12) | 0.310 (6) | 0.186 (2) | 0.038 (17)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0478 (8) | 0.0328 (7) | 0.0251 (6) | −0.0078 (7) | −0.0035 (6) | 0.0063 (5) |
S2 | 0.0565 (9) | 0.0363 (8) | 0.0268 (6) | −0.0148 (7) | −0.0087 (6) | −0.0006 (6) |
O1 | 0.063 (3) | 0.053 (3) | 0.026 (2) | −0.023 (2) | 0.003 (2) | 0.0027 (19) |
N1 | 0.039 (2) | 0.022 (2) | 0.0245 (19) | −0.006 (2) | −0.0022 (18) | −0.0008 (17) |
N2 | 0.049 (3) | 0.033 (2) | 0.0221 (18) | −0.009 (2) | −0.0053 (19) | −0.0003 (18) |
C1 | 0.043 (3) | 0.029 (3) | 0.032 (2) | −0.006 (2) | −0.002 (2) | 0.003 (2) |
C2 | 0.065 (4) | 0.047 (4) | 0.024 (2) | −0.014 (3) | 0.002 (3) | −0.004 (3) |
C3 | 0.058 (4) | 0.045 (4) | 0.034 (3) | −0.015 (3) | −0.004 (3) | −0.011 (3) |
C4 | 0.039 (3) | 0.018 (2) | 0.040 (3) | 0.002 (2) | −0.002 (2) | −0.006 (2) |
C5 | 0.041 (3) | 0.029 (3) | 0.043 (3) | −0.003 (3) | 0.002 (3) | −0.009 (2) |
C6 | 0.036 (3) | 0.028 (3) | 0.050 (3) | −0.002 (2) | 0.006 (3) | 0.000 (3) |
C7 | 0.053 (4) | 0.037 (3) | 0.041 (3) | −0.007 (3) | 0.001 (3) | 0.006 (3) |
C8 | 0.042 (3) | 0.030 (3) | 0.026 (2) | −0.006 (3) | 0.001 (2) | 0.002 (2) |
C9 | 0.034 (3) | 0.020 (2) | 0.029 (2) | 0.003 (2) | −0.001 (2) | 0.0012 (19) |
C10 | 0.036 (3) | 0.017 (2) | 0.026 (2) | 0.002 (2) | 0.000 (2) | −0.0034 (19) |
C11 | 0.039 (3) | 0.024 (2) | 0.025 (2) | −0.001 (3) | 0.001 (2) | −0.0018 (19) |
C12 | 0.042 (3) | 0.015 (2) | 0.024 (2) | 0.001 (2) | 0.000 (2) | 0.0008 (18) |
C13 | 0.055 (4) | 0.035 (3) | 0.043 (3) | −0.013 (3) | 0.002 (3) | 0.011 (3) |
S1—C12 | 1.751 (5) | C4—C5 | 1.427 (7) |
S1—C13 | 1.786 (6) | C5—C6 | 1.352 (7) |
S2—C12 | 1.664 (5) | C5—H5 | 0.9300 |
O1—C1 | 1.348 (7) | C6—C7 | 1.411 (8) |
O1—H1A | 0.79 (6) | C6—H6 | 0.9300 |
N1—C11 | 1.284 (6) | C7—C8 | 1.363 (8) |
N1—N2 | 1.368 (5) | C7—H7 | 0.9300 |
N2—C12 | 1.325 (6) | C8—C9 | 1.413 (6) |
N2—H2A | 0.8600 | C8—H8 | 0.9300 |
C1—C10 | 1.395 (7) | C9—C10 | 1.435 (7) |
C1—C2 | 1.397 (8) | C10—C11 | 1.453 (7) |
C2—C3 | 1.356 (8) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C13—H13C | 0.9600 |
C3—C4 | 1.424 (7) | C13—H13A | 0.9600 |
C3—H3 | 0.9300 | C13—H13B | 0.9600 |
C4—C9 | 1.416 (7) | ||
C12—S1—C13 | 102.9 (3) | C8—C7—C6 | 120.6 (5) |
C1—O1—H1A | 104 (4) | C8—C7—H7 | 119.7 |
C11—N1—N2 | 117.0 (4) | C6—C7—H7 | 119.7 |
C12—N2—N1 | 122.2 (4) | C7—C8—C9 | 121.8 (5) |
C12—N2—H2A | 118.9 | C7—C8—H8 | 119.1 |
N1—N2—H2A | 118.9 | C9—C8—H8 | 119.1 |
O1—C1—C10 | 123.7 (5) | C8—C9—C4 | 116.9 (5) |
O1—C1—C2 | 115.9 (5) | C8—C9—C10 | 123.7 (5) |
C10—C1—C2 | 120.5 (5) | C4—C9—C10 | 119.3 (4) |
C3—C2—C1 | 121.2 (5) | C1—C10—C9 | 119.2 (5) |
C3—C2—H2 | 119.4 | C1—C10—C11 | 120.6 (5) |
C1—C2—H2 | 119.4 | C9—C10—C11 | 120.2 (4) |
C2—C3—C4 | 120.8 (5) | N1—C11—C10 | 122.6 (4) |
C2—C3—H3 | 119.6 | N1—C11—H11 | 118.7 |
C4—C3—H3 | 119.6 | C10—C11—H11 | 118.7 |
C9—C4—C3 | 118.9 (5) | N2—C12—S2 | 122.9 (4) |
C9—C4—C5 | 120.5 (5) | N2—C12—S1 | 112.5 (4) |
C3—C4—C5 | 120.6 (5) | S2—C12—S1 | 124.6 (3) |
C6—C5—C4 | 120.2 (5) | S1—C13—H13C | 109.5 |
C6—C5—H5 | 119.9 | S1—C13—H13A | 109.5 |
C4—C5—H5 | 119.9 | H13C—C13—H13A | 109.5 |
C5—C6—C7 | 120.0 (5) | S1—C13—H13B | 109.5 |
C5—C6—H6 | 120.0 | H13C—C13—H13B | 109.5 |
C7—C6—H6 | 120.0 | H13A—C13—H13B | 109.5 |
C11—N1—N2—C12 | 178.2 (5) | C5—C4—C9—C10 | 179.5 (5) |
O1—C1—C2—C3 | 179.3 (6) | O1—C1—C10—C9 | −179.8 (5) |
C10—C1—C2—C3 | −2.5 (10) | C2—C1—C10—C9 | 2.1 (8) |
C1—C2—C3—C4 | 0.7 (10) | O1—C1—C10—C11 | 0.3 (8) |
C2—C3—C4—C9 | 1.5 (9) | C2—C1—C10—C11 | −177.8 (5) |
C2—C3—C4—C5 | −179.8 (6) | C8—C9—C10—C1 | 179.5 (5) |
C9—C4—C5—C6 | 0.8 (8) | C4—C9—C10—C1 | 0.0 (7) |
C3—C4—C5—C6 | −177.9 (6) | C8—C9—C10—C11 | −0.6 (7) |
C4—C5—C6—C7 | −1.5 (9) | C4—C9—C10—C11 | 179.9 (5) |
C5—C6—C7—C8 | 1.3 (9) | N2—N1—C11—C10 | 179.7 (4) |
C6—C7—C8—C9 | −0.5 (9) | C1—C10—C11—N1 | 0.4 (8) |
C7—C8—C9—C4 | −0.2 (8) | C9—C10—C11—N1 | −179.5 (5) |
C7—C8—C9—C10 | −179.7 (5) | N1—N2—C12—S2 | 179.0 (4) |
C3—C4—C9—C8 | 178.7 (5) | N1—N2—C12—S1 | −1.3 (6) |
C5—C4—C9—C8 | 0.0 (7) | C13—S1—C12—N2 | −179.2 (4) |
C3—C4—C9—C10 | −1.8 (8) | C13—S1—C12—S2 | 0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N1 | 0.79 (6) | 1.90 (5) | 2.634 (5) | 153 (6) |
C11—H11···S2i | 0.93 | 2.94 | 3.780 (5) | 150 |
N2—H2A···S2i | 0.86 | 2.64 | 3.482 (4) | 165 |
C2—H2···S1ii | 0.93 | 2.90 | 3.573 (6) | 130 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x+2, y+1/2, −z+1/2. |