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The mol­ecule of the title compound, C5H4ClNO2, is essentially planar, with normal values for the bond lengths and angles. In the crystal structure, inter­molecular O—H...N hydrogen bonds link the mol­ecules into zigzag chains extending along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601508X/cv2046sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680601508X/cv2046Isup2.hkl
Contains datablock I

CCDC reference: 608419

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.136
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

(Z)-5-Chlorofuran-2-carbaldehyde oxime top
Crystal data top
C5H4ClNO2F(000) = 296
Mr = 145.54Dx = 1.608 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3079 reflections
a = 9.394 (3) Åθ = 2.3–23.0°
b = 5.0879 (15) ŵ = 0.55 mm1
c = 12.870 (4) ÅT = 298 K
β = 102.301 (4)°Block, colourless
V = 601.0 (3) Å30.41 × 0.34 × 0.25 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1055 independent reflections
Radiation source: fine-focus sealed tube910 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 118
Tmin = 0.807, Tmax = 0.875k = 65
2747 measured reflectionsl = 1513
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0777P)2 + 0.2968P]
where P = (Fo2 + 2Fc2)/3
1055 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.28 e Å3
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.13446 (8)0.22129 (16)0.51656 (6)0.0622 (4)
O10.35953 (18)0.2213 (3)0.43231 (13)0.0396 (5)
O20.6067 (2)0.5928 (4)0.25446 (15)0.0515 (5)
H2A0.66630.64750.22150.077*
N10.6512 (2)0.3476 (4)0.29819 (17)0.0426 (5)
C10.2395 (2)0.3608 (5)0.44027 (19)0.0388 (6)
C20.2291 (3)0.5858 (5)0.3861 (2)0.0418 (6)
H2B0.15610.71170.38040.050*
C30.3525 (3)0.5937 (5)0.33906 (19)0.0383 (6)
H3A0.37590.72680.29610.046*
C40.4297 (2)0.3709 (5)0.36835 (17)0.0339 (6)
C50.5617 (3)0.2537 (5)0.3502 (2)0.0397 (6)
H5A0.58460.08880.38030.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0547 (5)0.0689 (6)0.0750 (6)0.0042 (3)0.0405 (4)0.0070 (4)
O10.0382 (10)0.0375 (9)0.0485 (10)0.0016 (7)0.0217 (8)0.0071 (7)
O20.0466 (10)0.0503 (11)0.0670 (12)0.0028 (9)0.0331 (9)0.0127 (9)
N10.0371 (11)0.0439 (12)0.0519 (12)0.0005 (9)0.0208 (9)0.0039 (10)
C10.0342 (13)0.0444 (14)0.0423 (13)0.0029 (10)0.0183 (10)0.0058 (11)
C20.0385 (13)0.0396 (14)0.0519 (14)0.0066 (11)0.0197 (11)0.0015 (11)
C30.0405 (13)0.0345 (12)0.0435 (12)0.0000 (10)0.0173 (10)0.0015 (10)
C40.0349 (12)0.0336 (12)0.0368 (12)0.0055 (10)0.0155 (9)0.0015 (9)
C50.0379 (13)0.0360 (13)0.0492 (14)0.0024 (10)0.0181 (11)0.0004 (10)
Geometric parameters (Å, º) top
Cl1—C11.690 (2)C2—C31.418 (3)
O1—C11.354 (3)C2—H2B0.9300
O1—C41.387 (3)C3—C41.355 (3)
O2—N11.395 (3)C3—H3A0.9300
O2—H2A0.8200C4—C51.439 (3)
N1—C51.274 (3)C5—H5A0.9300
C1—C21.333 (4)
C1—O1—C4105.41 (18)C4—C3—C2107.2 (2)
N1—O2—H2A109.5C4—C3—H3A126.4
C5—N1—O2111.88 (19)C2—C3—H3A126.4
C2—C1—O1112.3 (2)C3—C4—O1109.29 (19)
C2—C1—Cl1132.67 (19)C3—C4—C5136.9 (2)
O1—C1—Cl1115.00 (18)O1—C4—C5113.8 (2)
C1—C2—C3105.8 (2)N1—C5—C4128.2 (2)
C1—C2—H2B127.1N1—C5—H5A115.9
C3—C2—H2B127.1C4—C5—H5A115.9
C4—O1—C1—C20.1 (3)C2—C3—C4—C5179.9 (3)
C4—O1—C1—Cl1179.24 (15)C1—O1—C4—C30.1 (3)
O1—C1—C2—C30.0 (3)C1—O1—C4—C5179.99 (19)
Cl1—C1—C2—C3179.2 (2)O2—N1—C5—C41.1 (4)
C1—C2—C3—C40.1 (3)C3—C4—C5—N12.7 (5)
C2—C3—C4—O10.1 (3)O1—C4—C5—N1177.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···N1i0.822.052.823 (3)156
Symmetry code: (i) x+3/2, y+1/2, z+1/2.
 

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