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The title compound, C7H7NO3S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022415/rz6099sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022415/rz6099Isup2.hkl
Contains datablock I

CCDC reference: 282585

Key indicators

  • Single-crystal X-ray study
  • T = 303 K
  • Mean [sigma](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

Computing details top

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
C7H7NO3SF(000) = 768
Mr = 185.20Dx = 1.562 Mg m3
Monoclinic, P21/cMelting point: 482 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.826 (4) ÅCell parameters from 25 reflections
b = 13.596 (2) Åθ = 2–25°
c = 11.990 (5) ŵ = 0.37 mm1
β = 102.06 (4)°T = 303 K
V = 1566.6 (10) Å3Prism, white
Z = 80.24 × 0.20 × 0.18 mm
Data collection top
Nonius MACH3 sealed-tube
diffractometer
Rint = 0.060
ω–2θ scansθmax = 25.0°, θmin = 2.1°
Absorption correction: ψ scan
(North et al., 1968)
h = 011
Tmin = 0.914, Tmax = 0.935k = 116
3186 measured reflectionsl = 1413
2751 independent reflections3 standard reflections every 60 min
1546 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullAll 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 = 1.02Δρmax = 0.34 e Å3
2751 reflectionsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
C10.7804 (4)1.0868 (3)0.0244 (4)0.0348 (10)
C20.6995 (4)1.0116 (3)0.0763 (3)0.0340 (10)
H2A0.76210.96390.12020.041*
H2B0.63470.97710.01710.041*
C30.5158 (4)0.9831 (3)0.2161 (3)0.0305 (9)
C40.5059 (4)0.8859 (3)0.1841 (4)0.0357 (10)
H40.55270.8630.12940.043*
C50.4262 (5)0.8225 (3)0.2333 (4)0.0435 (12)
H50.41690.75720.20980.052*
C60.3602 (5)0.8548 (3)0.3168 (4)0.0460 (12)
H60.30860.81170.35180.055*
C70.3721 (5)0.9512 (3)0.3472 (4)0.0458 (13)
H70.32770.97430.40330.055*
C110.2918 (4)0.3235 (3)0.0317 (4)0.0355 (10)
C120.2326 (5)0.2477 (3)0.0999 (4)0.0356 (10)
H12A0.30660.2080.14420.043*
H12B0.1690.20460.04950.043*
C130.0714 (4)0.2161 (3)0.2555 (3)0.0302 (10)
C140.0822 (5)0.1161 (3)0.2376 (4)0.0381 (11)
H140.13480.0930.1870.046*
C150.0153 (5)0.0522 (3)0.2947 (4)0.0442 (12)
H150.02170.0150.28230.053*
C160.0617 (5)0.0849 (3)0.3704 (4)0.0446 (11)
H160.10790.04060.40860.054*
C170.0694 (5)0.1838 (3)0.3888 (4)0.0408 (11)
H170.12180.20720.43940.049*
N10.4473 (4)1.0137 (2)0.2972 (3)0.0374 (9)
N110.0016 (4)0.2469 (2)0.3341 (3)0.0352 (9)
O10.7865 (3)1.1724 (2)0.0509 (3)0.0518 (9)
O20.8412 (4)1.0477 (2)0.0519 (3)0.0489 (9)
H20.88661.08990.07680.073*
O30.4564 (4)1.1086 (2)0.3228 (3)0.0598 (11)
O110.2770 (3)0.4108 (2)0.0426 (3)0.0486 (9)
O120.3582 (4)0.2836 (2)0.0398 (3)0.0475 (9)
H120.39010.32690.07450.071*
O130.0026 (3)0.3426 (2)0.3535 (3)0.0503 (9)
S80.60680 (12)1.07807 (8)0.16754 (10)0.0393 (3)
S200.14192 (12)0.31331 (7)0.19280 (10)0.0382 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.035 (2)0.039 (2)0.034 (2)0.005 (2)0.016 (2)0.001 (2)
C20.037 (2)0.036 (2)0.032 (2)0.0010 (19)0.014 (2)0.0016 (19)
C30.029 (2)0.035 (2)0.030 (2)0.0011 (18)0.0105 (19)0.0001 (19)
C40.043 (3)0.031 (2)0.037 (3)0.0037 (19)0.018 (2)0.0014 (19)
C50.052 (3)0.029 (2)0.052 (3)0.001 (2)0.015 (2)0.000 (2)
C60.052 (3)0.037 (2)0.056 (3)0.005 (2)0.027 (3)0.011 (2)
C70.053 (3)0.043 (3)0.050 (3)0.001 (2)0.033 (3)0.009 (2)
C110.035 (2)0.042 (3)0.031 (2)0.001 (2)0.012 (2)0.003 (2)
C120.038 (3)0.039 (2)0.034 (2)0.002 (2)0.016 (2)0.005 (2)
C130.029 (2)0.037 (2)0.026 (2)0.0011 (18)0.0081 (19)0.0007 (18)
C140.040 (3)0.031 (2)0.046 (3)0.0012 (19)0.016 (2)0.005 (2)
C150.054 (3)0.031 (2)0.049 (3)0.001 (2)0.011 (2)0.000 (2)
C160.049 (3)0.042 (3)0.046 (3)0.011 (2)0.017 (2)0.008 (2)
C170.045 (3)0.044 (3)0.040 (3)0.003 (2)0.025 (2)0.002 (2)
N10.046 (2)0.0294 (19)0.042 (2)0.0046 (16)0.0237 (19)0.0026 (17)
N110.043 (2)0.0314 (19)0.035 (2)0.0013 (16)0.0165 (18)0.0000 (16)
O10.069 (2)0.0386 (19)0.057 (2)0.0084 (16)0.0357 (19)0.0073 (16)
O20.063 (2)0.0405 (17)0.056 (2)0.0014 (16)0.0406 (18)0.0031 (16)
O30.089 (3)0.0330 (17)0.075 (3)0.0089 (17)0.058 (2)0.0095 (17)
O110.066 (2)0.0370 (18)0.051 (2)0.0020 (16)0.0319 (18)0.0016 (15)
O120.067 (2)0.0402 (17)0.047 (2)0.0019 (16)0.0382 (18)0.0018 (15)
O130.071 (2)0.0296 (16)0.065 (2)0.0002 (15)0.0466 (19)0.0051 (15)
S80.0490 (7)0.0327 (6)0.0442 (7)0.0039 (5)0.0278 (6)0.0044 (5)
S200.0504 (7)0.0292 (6)0.0421 (7)0.0002 (5)0.0257 (6)0.0012 (5)
Geometric parameters (Å, º) top
C1—O11.205 (5)C11—C121.507 (6)
C1—O21.306 (5)C12—S201.802 (4)
C1—C21.508 (6)C12—H12A0.97
C2—S81.806 (4)C12—H12B0.97
C2—H2A0.97C13—N111.364 (5)
C2—H2B0.97C13—C141.383 (5)
C3—N11.359 (5)C13—S201.736 (4)
C3—C41.374 (6)C14—C151.360 (6)
C3—S81.739 (4)C14—H140.93
C4—C51.378 (6)C15—C161.372 (6)
C4—H40.93C15—H150.93
C5—C61.373 (6)C16—C171.366 (6)
C5—H50.93C16—H160.93
C6—C71.359 (6)C17—N111.340 (5)
C6—H60.93C17—H170.93
C7—N11.346 (5)N1—O31.324 (4)
C7—H70.93N11—O131.323 (4)
C11—O111.206 (5)O2—H20.82
C11—O121.299 (5)O12—H120.82
O1—C1—O2125.0 (4)S20—C12—H12A110.3
O1—C1—C2123.2 (4)C11—C12—H12B110.3
O2—C1—C2111.8 (4)S20—C12—H12B110.3
C1—C2—S8106.7 (3)H12A—C12—H12B108.6
C1—C2—H2A110.4N11—C13—C14118.6 (4)
S8—C2—H2A110.4N11—C13—S20112.3 (3)
C1—C2—H2B110.4C14—C13—S20129.1 (3)
S8—C2—H2B110.4C15—C14—C13119.3 (4)
H2A—C2—H2B108.6C15—C14—H14120.4
N1—C3—C4118.5 (4)C13—C14—H14120.4
N1—C3—S8112.2 (3)C14—C15—C16121.2 (4)
C4—C3—S8129.2 (3)C14—C15—H15119.4
C3—C4—C5119.7 (4)C16—C15—H15119.4
C3—C4—H4120.1C17—C16—C15118.9 (4)
C5—C4—H4120.1C17—C16—H16120.6
C6—C5—C4120.6 (4)C15—C16—H16120.6
C6—C5—H5119.7N11—C17—C16120.1 (4)
C4—C5—H5119.7N11—C17—H17119.9
C7—C6—C5118.5 (4)C16—C17—H17119.9
C7—C6—H6120.8O3—N1—C7122.0 (3)
C5—C6—H6120.8O3—N1—C3116.4 (3)
N1—C7—C6121.0 (4)C7—N1—C3121.7 (4)
N1—C7—H7119.5O13—N11—C17121.4 (3)
C6—C7—H7119.5O13—N11—C13116.7 (3)
O11—C11—O12124.9 (4)C17—N11—C13121.9 (3)
O11—C11—C12123.0 (4)C1—O2—H2109.5
O12—C11—C12112.1 (4)C11—O12—H12109.5
C11—C12—S20107.1 (3)C3—S8—C2101.01 (19)
C11—C12—H12A110.3C13—S20—C12100.62 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O13i0.821.762.568 (5)167
O12—H12···O3ii0.821.742.541 (5)163
C4—H4···O12iii0.932.513.325 (6)147
C14—H14···O2iii0.932.553.344 (6)144
C6—H6···O1iv0.932.513.420 (6)168
C5—H5···O3iv0.932.453.250 (5)144
C7—H7···O11v0.932.413.286 (6)156
C15—H15···O13vi0.932.513.347 (5)149
C16—H16···O11vi0.932.573.477 (6)164
C17—H17···O1vii0.932.403.279 (6)157
Symmetry codes: (i) x+1, y+3/2, z1/2; (ii) x, y+3/2, z1/2; (iii) x+1, y+1, z; (iv) x+1, y1/2, z+1/2; (v) x, y+3/2, z+1/2; (vi) x, y1/2, z+1/2; (vii) x1, y+3/2, z+1/2.
 

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