The title compound, C
7H
7NO
3S, is a simple new pyridylthio-
N-oxide of pharmacological interest. There are two independent molecules in the asymmetric unit. Strong O—H
O hydrogen-bond interactions link the molecules in ribbons lying in the (101) plane.
Supporting information
CCDC reference: 282585
Key indicators
- Single-crystal X-ray study
- T = 303 K
- Mean (C-C) = 0.006 Å
- R factor = 0.052
- wR factor = 0.150
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.21
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
2-(Acetylsulfanyl)pyridine N-oxide
top
Crystal data top
C7H7NO3S | F(000) = 768 |
Mr = 185.20 | Dx = 1.562 Mg m−3 |
Monoclinic, P21/c | Melting point: 482 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.826 (4) Å | Cell parameters from 25 reflections |
b = 13.596 (2) Å | θ = 2–25° |
c = 11.990 (5) Å | µ = 0.37 mm−1 |
β = 102.06 (4)° | T = 303 K |
V = 1566.6 (10) Å3 | Prism, white |
Z = 8 | 0.24 × 0.20 × 0.18 mm |
Data collection top
Nonius MACH3 sealed-tube diffractometer | Rint = 0.060 |
ω–2θ scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→11 |
Tmin = 0.914, Tmax = 0.935 | k = −1→16 |
3186 measured reflections | l = −14→13 |
2751 independent reflections | 3 standard reflections every 60 min |
1546 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.150 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.34 e Å−3 |
2751 reflections | Δρmin = −0.33 e Å−3 |
219 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.7804 (4) | 1.0868 (3) | 0.0244 (4) | 0.0348 (10) | |
C2 | 0.6995 (4) | 1.0116 (3) | 0.0763 (3) | 0.0340 (10) | |
H2A | 0.7621 | 0.9639 | 0.1202 | 0.041* | |
H2B | 0.6347 | 0.9771 | 0.0171 | 0.041* | |
C3 | 0.5158 (4) | 0.9831 (3) | 0.2161 (3) | 0.0305 (9) | |
C4 | 0.5059 (4) | 0.8859 (3) | 0.1841 (4) | 0.0357 (10) | |
H4 | 0.5527 | 0.863 | 0.1294 | 0.043* | |
C5 | 0.4262 (5) | 0.8225 (3) | 0.2333 (4) | 0.0435 (12) | |
H5 | 0.4169 | 0.7572 | 0.2098 | 0.052* | |
C6 | 0.3602 (5) | 0.8548 (3) | 0.3168 (4) | 0.0460 (12) | |
H6 | 0.3086 | 0.8117 | 0.3518 | 0.055* | |
C7 | 0.3721 (5) | 0.9512 (3) | 0.3472 (4) | 0.0458 (13) | |
H7 | 0.3277 | 0.9743 | 0.4033 | 0.055* | |
C11 | 0.2918 (4) | 0.3235 (3) | 0.0317 (4) | 0.0355 (10) | |
C12 | 0.2326 (5) | 0.2477 (3) | 0.0999 (4) | 0.0356 (10) | |
H12A | 0.3066 | 0.208 | 0.1442 | 0.043* | |
H12B | 0.169 | 0.2046 | 0.0495 | 0.043* | |
C13 | 0.0714 (4) | 0.2161 (3) | 0.2555 (3) | 0.0302 (10) | |
C14 | 0.0822 (5) | 0.1161 (3) | 0.2376 (4) | 0.0381 (11) | |
H14 | 0.1348 | 0.093 | 0.187 | 0.046* | |
C15 | 0.0153 (5) | 0.0522 (3) | 0.2947 (4) | 0.0442 (12) | |
H15 | 0.0217 | −0.015 | 0.2823 | 0.053* | |
C16 | −0.0617 (5) | 0.0849 (3) | 0.3704 (4) | 0.0446 (11) | |
H16 | −0.1079 | 0.0406 | 0.4086 | 0.054* | |
C17 | −0.0694 (5) | 0.1838 (3) | 0.3888 (4) | 0.0408 (11) | |
H17 | −0.1218 | 0.2072 | 0.4394 | 0.049* | |
N1 | 0.4473 (4) | 1.0137 (2) | 0.2972 (3) | 0.0374 (9) | |
N11 | −0.0016 (4) | 0.2469 (2) | 0.3341 (3) | 0.0352 (9) | |
O1 | 0.7865 (3) | 1.1724 (2) | 0.0509 (3) | 0.0518 (9) | |
O2 | 0.8412 (4) | 1.0477 (2) | −0.0519 (3) | 0.0489 (9) | |
H2 | 0.8866 | 1.0899 | −0.0768 | 0.073* | |
O3 | 0.4564 (4) | 1.1086 (2) | 0.3228 (3) | 0.0598 (11) | |
O11 | 0.2770 (3) | 0.4108 (2) | 0.0426 (3) | 0.0486 (9) | |
O12 | 0.3582 (4) | 0.2836 (2) | −0.0398 (3) | 0.0475 (9) | |
H12 | 0.3901 | 0.3269 | −0.0745 | 0.071* | |
O13 | −0.0026 (3) | 0.3426 (2) | 0.3535 (3) | 0.0503 (9) | |
S8 | 0.60680 (12) | 1.07807 (8) | 0.16754 (10) | 0.0393 (3) | |
S20 | 0.14192 (12) | 0.31331 (7) | 0.19280 (10) | 0.0382 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.035 (2) | 0.039 (2) | 0.034 (2) | 0.005 (2) | 0.016 (2) | 0.001 (2) |
C2 | 0.037 (2) | 0.036 (2) | 0.032 (2) | 0.0010 (19) | 0.014 (2) | −0.0016 (19) |
C3 | 0.029 (2) | 0.035 (2) | 0.030 (2) | 0.0011 (18) | 0.0105 (19) | −0.0001 (19) |
C4 | 0.043 (3) | 0.031 (2) | 0.037 (3) | 0.0037 (19) | 0.018 (2) | −0.0014 (19) |
C5 | 0.052 (3) | 0.029 (2) | 0.052 (3) | 0.001 (2) | 0.015 (2) | 0.000 (2) |
C6 | 0.052 (3) | 0.037 (2) | 0.056 (3) | −0.005 (2) | 0.027 (3) | 0.011 (2) |
C7 | 0.053 (3) | 0.043 (3) | 0.050 (3) | −0.001 (2) | 0.033 (3) | 0.009 (2) |
C11 | 0.035 (2) | 0.042 (3) | 0.031 (2) | 0.001 (2) | 0.012 (2) | 0.003 (2) |
C12 | 0.038 (3) | 0.039 (2) | 0.034 (2) | 0.002 (2) | 0.016 (2) | −0.005 (2) |
C13 | 0.029 (2) | 0.037 (2) | 0.026 (2) | −0.0011 (18) | 0.0081 (19) | 0.0007 (18) |
C14 | 0.040 (3) | 0.031 (2) | 0.046 (3) | 0.0012 (19) | 0.016 (2) | −0.005 (2) |
C15 | 0.054 (3) | 0.031 (2) | 0.049 (3) | −0.001 (2) | 0.011 (2) | 0.000 (2) |
C16 | 0.049 (3) | 0.042 (3) | 0.046 (3) | −0.011 (2) | 0.017 (2) | 0.008 (2) |
C17 | 0.045 (3) | 0.044 (3) | 0.040 (3) | −0.003 (2) | 0.025 (2) | 0.002 (2) |
N1 | 0.046 (2) | 0.0294 (19) | 0.042 (2) | 0.0046 (16) | 0.0237 (19) | 0.0026 (17) |
N11 | 0.043 (2) | 0.0314 (19) | 0.035 (2) | −0.0013 (16) | 0.0165 (18) | 0.0000 (16) |
O1 | 0.069 (2) | 0.0386 (19) | 0.057 (2) | −0.0084 (16) | 0.0357 (19) | −0.0073 (16) |
O2 | 0.063 (2) | 0.0405 (17) | 0.056 (2) | −0.0014 (16) | 0.0406 (18) | −0.0031 (16) |
O3 | 0.089 (3) | 0.0330 (17) | 0.075 (3) | −0.0089 (17) | 0.058 (2) | −0.0095 (17) |
O11 | 0.066 (2) | 0.0370 (18) | 0.051 (2) | 0.0020 (16) | 0.0319 (18) | 0.0016 (15) |
O12 | 0.067 (2) | 0.0402 (17) | 0.047 (2) | 0.0019 (16) | 0.0382 (18) | −0.0018 (15) |
O13 | 0.071 (2) | 0.0296 (16) | 0.065 (2) | 0.0002 (15) | 0.0466 (19) | −0.0051 (15) |
S8 | 0.0490 (7) | 0.0327 (6) | 0.0442 (7) | −0.0039 (5) | 0.0278 (6) | −0.0044 (5) |
S20 | 0.0504 (7) | 0.0292 (6) | 0.0421 (7) | −0.0002 (5) | 0.0257 (6) | −0.0012 (5) |
Geometric parameters (Å, º) top
C1—O1 | 1.205 (5) | C11—C12 | 1.507 (6) |
C1—O2 | 1.306 (5) | C12—S20 | 1.802 (4) |
C1—C2 | 1.508 (6) | C12—H12A | 0.97 |
C2—S8 | 1.806 (4) | C12—H12B | 0.97 |
C2—H2A | 0.97 | C13—N11 | 1.364 (5) |
C2—H2B | 0.97 | C13—C14 | 1.383 (5) |
C3—N1 | 1.359 (5) | C13—S20 | 1.736 (4) |
C3—C4 | 1.374 (6) | C14—C15 | 1.360 (6) |
C3—S8 | 1.739 (4) | C14—H14 | 0.93 |
C4—C5 | 1.378 (6) | C15—C16 | 1.372 (6) |
C4—H4 | 0.93 | C15—H15 | 0.93 |
C5—C6 | 1.373 (6) | C16—C17 | 1.366 (6) |
C5—H5 | 0.93 | C16—H16 | 0.93 |
C6—C7 | 1.359 (6) | C17—N11 | 1.340 (5) |
C6—H6 | 0.93 | C17—H17 | 0.93 |
C7—N1 | 1.346 (5) | N1—O3 | 1.324 (4) |
C7—H7 | 0.93 | N11—O13 | 1.323 (4) |
C11—O11 | 1.206 (5) | O2—H2 | 0.82 |
C11—O12 | 1.299 (5) | O12—H12 | 0.82 |
| | | |
O1—C1—O2 | 125.0 (4) | S20—C12—H12A | 110.3 |
O1—C1—C2 | 123.2 (4) | C11—C12—H12B | 110.3 |
O2—C1—C2 | 111.8 (4) | S20—C12—H12B | 110.3 |
C1—C2—S8 | 106.7 (3) | H12A—C12—H12B | 108.6 |
C1—C2—H2A | 110.4 | N11—C13—C14 | 118.6 (4) |
S8—C2—H2A | 110.4 | N11—C13—S20 | 112.3 (3) |
C1—C2—H2B | 110.4 | C14—C13—S20 | 129.1 (3) |
S8—C2—H2B | 110.4 | C15—C14—C13 | 119.3 (4) |
H2A—C2—H2B | 108.6 | C15—C14—H14 | 120.4 |
N1—C3—C4 | 118.5 (4) | C13—C14—H14 | 120.4 |
N1—C3—S8 | 112.2 (3) | C14—C15—C16 | 121.2 (4) |
C4—C3—S8 | 129.2 (3) | C14—C15—H15 | 119.4 |
C3—C4—C5 | 119.7 (4) | C16—C15—H15 | 119.4 |
C3—C4—H4 | 120.1 | C17—C16—C15 | 118.9 (4) |
C5—C4—H4 | 120.1 | C17—C16—H16 | 120.6 |
C6—C5—C4 | 120.6 (4) | C15—C16—H16 | 120.6 |
C6—C5—H5 | 119.7 | N11—C17—C16 | 120.1 (4) |
C4—C5—H5 | 119.7 | N11—C17—H17 | 119.9 |
C7—C6—C5 | 118.5 (4) | C16—C17—H17 | 119.9 |
C7—C6—H6 | 120.8 | O3—N1—C7 | 122.0 (3) |
C5—C6—H6 | 120.8 | O3—N1—C3 | 116.4 (3) |
N1—C7—C6 | 121.0 (4) | C7—N1—C3 | 121.7 (4) |
N1—C7—H7 | 119.5 | O13—N11—C17 | 121.4 (3) |
C6—C7—H7 | 119.5 | O13—N11—C13 | 116.7 (3) |
O11—C11—O12 | 124.9 (4) | C17—N11—C13 | 121.9 (3) |
O11—C11—C12 | 123.0 (4) | C1—O2—H2 | 109.5 |
O12—C11—C12 | 112.1 (4) | C11—O12—H12 | 109.5 |
C11—C12—S20 | 107.1 (3) | C3—S8—C2 | 101.01 (19) |
C11—C12—H12A | 110.3 | C13—S20—C12 | 100.62 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O13i | 0.82 | 1.76 | 2.568 (5) | 167 |
O12—H12···O3ii | 0.82 | 1.74 | 2.541 (5) | 163 |
C4—H4···O12iii | 0.93 | 2.51 | 3.325 (6) | 147 |
C14—H14···O2iii | 0.93 | 2.55 | 3.344 (6) | 144 |
C6—H6···O1iv | 0.93 | 2.51 | 3.420 (6) | 168 |
C5—H5···O3iv | 0.93 | 2.45 | 3.250 (5) | 144 |
C7—H7···O11v | 0.93 | 2.41 | 3.286 (6) | 156 |
C15—H15···O13vi | 0.93 | 2.51 | 3.347 (5) | 149 |
C16—H16···O11vi | 0.93 | 2.57 | 3.477 (6) | 164 |
C17—H17···O1vii | 0.93 | 2.40 | 3.279 (6) | 157 |
Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+3/2, z+1/2; (vi) −x, y−1/2, −z+1/2; (vii) x−1, −y+3/2, z+1/2. |