Download citation
Download citation
link to html
In the approximately planar molecule of the title compound, C14H9ClN2O2, an intra­molecular O—H...N hydrogen bond helps to establish the mol­ecular conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047052/hb2194sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047052/hb2194Isup2.hkl
Contains datablock I

CCDC reference: 629840

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.053
  • wR factor = 0.140
  • Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.67 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1 - H ... 1.07 Ang.
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.02 From the CIF: _reflns_number_total 1343 Count of symmetry unique reflns 1346 Completeness (_total/calc) 99.78% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; 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: SHELXTL (Siemens, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

2-[3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]phenol top
Crystal data top
C14H9ClN2O2F(000) = 280
Mr = 272.68Dx = 1.475 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 6.3900 (13) Åθ = 9–12°
b = 5.038 (1) ŵ = 0.31 mm1
c = 19.255 (4) ÅT = 293 K
β = 97.98 (3)°Block, colourless
V = 613.9 (2) Å30.30 × 0.20 × 0.10 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
904 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 26.0°, θmin = 1.1°
ω/2θ scansh = 07
Absorption correction: ψ scan
(North et al., 1968)
k = 06
Tmin = 0.913, Tmax = 0.970l = 2323
1466 measured reflections3 standard reflections every 200 reflections
1343 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140 w = 1/[σ2(Fo2) + (0.0624P)2 + 0.1265P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1343 reflectionsΔρmax = 0.21 e Å3
175 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (2)
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
Cl0.9006 (3)0.4011 (4)0.04725 (8)0.0737 (5)
C60.5783 (8)0.9310 (12)0.3471 (3)0.0498 (13)
O10.9467 (6)0.8104 (11)0.3699 (3)0.0774 (15)
O20.3393 (6)0.6909 (9)0.2622 (2)0.0629 (12)
N10.3522 (7)0.4873 (11)0.2124 (3)0.0628 (15)
N20.6734 (6)0.5767 (12)0.2703 (2)0.0480 (11)
C10.4186 (9)1.0959 (17)0.3644 (3)0.0630 (16)
H1B0.28201.07760.34090.076*
C20.4606 (11)1.2861 (15)0.4160 (3)0.0724 (19)
H2B0.35311.39610.42710.087*
C30.6621 (12)1.3119 (17)0.4509 (3)0.076 (2)
H3A0.69051.43930.48590.091*
C40.8199 (11)1.1538 (15)0.4349 (3)0.070 (2)
H4A0.95591.17650.45840.084*
C50.7819 (9)0.9577 (14)0.3838 (3)0.0593 (16)
C70.5387 (8)0.7289 (13)0.2950 (3)0.0496 (14)
C80.5527 (8)0.4313 (12)0.2198 (3)0.0491 (14)
C90.6360 (8)0.2240 (12)0.1771 (3)0.0478 (13)
C100.8482 (8)0.1519 (13)0.1918 (3)0.0579 (18)
H10A0.93600.23360.22810.070*
C110.9271 (9)0.0437 (14)0.1515 (3)0.0612 (16)
H11A1.06730.09730.16150.073*
C120.7985 (10)0.1555 (12)0.0977 (3)0.0557 (15)
C130.5886 (9)0.0883 (15)0.0814 (3)0.0637 (18)
H13A0.50220.17120.04500.076*
C140.5106 (8)0.1086 (17)0.1217 (3)0.0591 (15)
H14A0.37080.16280.11080.071*
H0.903 (9)0.678 (15)0.327 (3)0.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0897 (11)0.0604 (9)0.0744 (10)0.0075 (11)0.0233 (8)0.0019 (10)
C60.054 (3)0.040 (3)0.056 (3)0.012 (3)0.012 (3)0.005 (3)
O10.052 (2)0.077 (3)0.098 (3)0.002 (3)0.007 (2)0.013 (3)
O20.048 (2)0.066 (3)0.073 (3)0.002 (2)0.0028 (19)0.006 (2)
N10.040 (3)0.073 (4)0.073 (3)0.002 (3)0.001 (2)0.010 (3)
N20.042 (2)0.050 (3)0.051 (2)0.009 (3)0.002 (2)0.004 (3)
C10.067 (4)0.057 (4)0.067 (4)0.001 (4)0.019 (3)0.005 (4)
C20.088 (5)0.060 (5)0.076 (4)0.007 (4)0.035 (4)0.004 (4)
C30.102 (6)0.060 (5)0.066 (4)0.019 (5)0.018 (4)0.004 (4)
C40.074 (4)0.062 (5)0.072 (4)0.013 (4)0.001 (3)0.001 (4)
C50.062 (4)0.057 (4)0.059 (3)0.016 (4)0.008 (3)0.002 (4)
C70.045 (3)0.047 (3)0.056 (3)0.008 (3)0.005 (3)0.013 (3)
C80.042 (3)0.054 (4)0.050 (3)0.010 (3)0.002 (2)0.010 (3)
C90.043 (3)0.049 (3)0.050 (3)0.005 (3)0.002 (2)0.003 (3)
C100.052 (3)0.063 (5)0.056 (3)0.005 (3)0.002 (3)0.003 (4)
C110.047 (3)0.069 (4)0.066 (4)0.005 (3)0.004 (3)0.009 (4)
C120.068 (4)0.045 (4)0.057 (4)0.004 (3)0.016 (3)0.009 (3)
C130.056 (4)0.067 (5)0.066 (4)0.003 (4)0.001 (3)0.008 (4)
C140.052 (3)0.062 (4)0.061 (3)0.000 (4)0.002 (3)0.003 (4)
Geometric parameters (Å, º) top
Cl—C121.754 (6)C3—C41.354 (10)
C6—C11.392 (8)C3—H3A0.9300
C6—C51.398 (8)C4—C51.391 (9)
C6—C71.428 (8)C4—H4A0.9300
O1—C51.345 (7)C8—C91.474 (8)
O1—H1.06 (7)C9—C141.372 (8)
O2—C71.355 (6)C9—C101.394 (7)
O2—N11.415 (6)C10—C111.392 (8)
N1—C81.300 (7)C10—H10A0.9300
N2—C71.292 (7)C11—C121.353 (8)
N2—C81.367 (7)C11—H11A0.9300
C1—C21.379 (10)C12—C131.376 (8)
C1—H1B0.9300C13—C141.393 (9)
C2—C31.374 (9)C13—H13A0.9300
C2—H2B0.9300C14—H14A0.9300
C1—C6—C5119.0 (6)N2—C7—C6128.3 (5)
C1—C6—C7122.0 (5)O2—C7—C6119.5 (5)
C5—C6—C7119.0 (5)N1—C8—N2114.3 (5)
C5—O1—H112 (3)N1—C8—C9121.3 (5)
C7—O2—N1106.2 (4)N2—C8—C9124.4 (5)
C8—N1—O2103.4 (4)C14—C9—C10119.6 (6)
C7—N2—C8103.9 (4)C14—C9—C8121.1 (5)
C2—C1—C6120.7 (6)C10—C9—C8119.2 (5)
C2—C1—H1B119.6C11—C10—C9119.3 (5)
C6—C1—H1B119.6C11—C10—H10A120.4
C3—C2—C1119.6 (7)C9—C10—H10A120.4
C3—C2—H2B120.2C12—C11—C10119.6 (6)
C1—C2—H2B120.2C12—C11—H11A120.2
C4—C3—C2120.6 (7)C10—C11—H11A120.2
C4—C3—H3A119.7C11—C12—C13122.7 (6)
C2—C3—H3A119.7C11—C12—Cl119.0 (5)
C3—C4—C5121.1 (6)C13—C12—Cl118.3 (5)
C3—C4—H4A119.4C12—C13—C14117.5 (6)
C5—C4—H4A119.4C12—C13—H13A121.3
O1—C5—C4117.9 (6)C14—C13—H13A121.3
O1—C5—C6123.1 (6)C9—C14—C13121.3 (5)
C4—C5—C6118.9 (6)C9—C14—H14A119.4
N2—C7—O2112.1 (5)C13—C14—H14A119.4
C7—O2—N1—C81.1 (5)C5—C6—C7—O2176.1 (5)
C5—C6—C1—C21.1 (9)O2—N1—C8—N20.6 (6)
C7—C6—C1—C2178.7 (5)O2—N1—C8—C9179.7 (4)
C6—C1—C2—C30.4 (10)C7—N2—C8—N10.2 (7)
C1—C2—C3—C40.4 (11)C7—N2—C8—C9178.9 (5)
C2—C3—C4—C51.3 (11)N1—C8—C9—C149.0 (8)
C3—C4—C5—O1179.2 (6)N2—C8—C9—C14172.0 (6)
C3—C4—C5—C62.1 (9)N1—C8—C9—C10173.5 (6)
C1—C6—C5—O1178.9 (6)N2—C8—C9—C105.5 (8)
C7—C6—C5—O13.5 (9)C14—C9—C10—C112.4 (9)
C1—C6—C5—C42.0 (8)C8—C9—C10—C11180.0 (5)
C7—C6—C5—C4179.6 (5)C9—C10—C11—C121.8 (9)
C8—N2—C7—O21.0 (6)C10—C11—C12—C131.5 (9)
C8—N2—C7—C6177.0 (5)C10—C11—C12—Cl179.8 (4)
N1—O2—C7—N21.3 (6)C11—C12—C13—C141.8 (9)
N1—O2—C7—C6177.8 (4)Cl—C12—C13—C14179.5 (5)
C1—C6—C7—N2174.3 (6)C10—C9—C14—C132.8 (10)
C5—C6—C7—N28.1 (8)C8—C9—C14—C13179.7 (6)
C1—C6—C7—O21.5 (8)C12—C13—C14—C92.4 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H···N21.06 (7)1.78 (6)2.680 (6)139 (5)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds