2-[3-(4-Chloro­phen­yl)-1,2,4-oxadiazol-5-yl]phenol

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

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

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Computing details

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

Crystal data

C14H9ClN2O2	F(000) = 280
Mr = 272.68	Dx = 1.475 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 6.3900 (13) Å	θ = 9–12°
b = 5.038 (1) Å	µ = 0.31 mm^−1
c = 19.255 (4) Å	T = 293 K
β = 97.98 (3)°	Block, colourless
V = 613.9 (2) Å^3	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection

Enraf–Nonius CAD-4 diffractometer	904 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 26.0°, θmin = 1.1°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→6
Tmin = 0.913, Tmax = 0.970	l = −23→23
1466 measured reflections	3 standard reflections every 200 reflections
1343 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.140	w = 1/[σ^2(Fo^2) + (0.0624P)^2 + 0.1265P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1343 reflections	Δρmax = 0.21 e Å^−3
175 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.9006 (3)	−0.4011 (4)	0.04725 (8)	0.0737 (5)
C6	0.5783 (8)	0.9310 (12)	0.3471 (3)	0.0498 (13)
O1	0.9467 (6)	0.8104 (11)	0.3699 (3)	0.0774 (15)
O2	0.3393 (6)	0.6909 (9)	0.2622 (2)	0.0629 (12)
N1	0.3522 (7)	0.4873 (11)	0.2124 (3)	0.0628 (15)
N2	0.6734 (6)	0.5767 (12)	0.2703 (2)	0.0480 (11)
C1	0.4186 (9)	1.0959 (17)	0.3644 (3)	0.0630 (16)
H1B	0.2820	1.0776	0.3409	0.076*
C2	0.4606 (11)	1.2861 (15)	0.4160 (3)	0.0724 (19)
H2B	0.3531	1.3961	0.4271	0.087*
C3	0.6621 (12)	1.3119 (17)	0.4509 (3)	0.076 (2)
H3A	0.6905	1.4393	0.4859	0.091*
C4	0.8199 (11)	1.1538 (15)	0.4349 (3)	0.070 (2)
H4A	0.9559	1.1765	0.4584	0.084*
C5	0.7819 (9)	0.9577 (14)	0.3838 (3)	0.0593 (16)
C7	0.5387 (8)	0.7289 (13)	0.2950 (3)	0.0496 (14)
C8	0.5527 (8)	0.4313 (12)	0.2198 (3)	0.0491 (14)
C9	0.6360 (8)	0.2240 (12)	0.1771 (3)	0.0478 (13)
C10	0.8482 (8)	0.1519 (13)	0.1918 (3)	0.0579 (18)
H10A	0.9360	0.2336	0.2281	0.070*
C11	0.9271 (9)	−0.0437 (14)	0.1515 (3)	0.0612 (16)
H11A	1.0673	−0.0973	0.1615	0.073*
C12	0.7985 (10)	−0.1555 (12)	0.0977 (3)	0.0557 (15)
C13	0.5886 (9)	−0.0883 (15)	0.0814 (3)	0.0637 (18)
H13A	0.5022	−0.1712	0.0450	0.076*
C14	0.5106 (8)	0.1086 (17)	0.1217 (3)	0.0591 (15)
H14A	0.3708	0.1628	0.1108	0.071*
H	0.903 (9)	0.678 (15)	0.327 (3)	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0897 (11)	0.0604 (9)	0.0744 (10)	0.0075 (11)	0.0233 (8)	0.0019 (10)
C6	0.054 (3)	0.040 (3)	0.056 (3)	−0.012 (3)	0.012 (3)	0.005 (3)
O1	0.052 (2)	0.077 (3)	0.098 (3)	−0.002 (3)	−0.007 (2)	−0.013 (3)
O2	0.048 (2)	0.066 (3)	0.073 (3)	0.002 (2)	0.0028 (19)	−0.006 (2)
N1	0.040 (3)	0.073 (4)	0.073 (3)	0.002 (3)	0.001 (2)	−0.010 (3)
N2	0.042 (2)	0.050 (3)	0.051 (2)	−0.009 (3)	0.002 (2)	0.004 (3)
C1	0.067 (4)	0.057 (4)	0.067 (4)	−0.001 (4)	0.019 (3)	0.005 (4)
C2	0.088 (5)	0.060 (5)	0.076 (4)	−0.007 (4)	0.035 (4)	−0.004 (4)
C3	0.102 (6)	0.060 (5)	0.066 (4)	−0.019 (5)	0.018 (4)	−0.004 (4)
C4	0.074 (4)	0.062 (5)	0.072 (4)	−0.013 (4)	0.001 (3)	−0.001 (4)
C5	0.062 (4)	0.057 (4)	0.059 (3)	−0.016 (4)	0.008 (3)	0.002 (4)
C7	0.045 (3)	0.047 (3)	0.056 (3)	−0.008 (3)	0.005 (3)	0.013 (3)
C8	0.042 (3)	0.054 (4)	0.050 (3)	−0.010 (3)	0.002 (2)	0.010 (3)
C9	0.043 (3)	0.049 (3)	0.050 (3)	−0.005 (3)	0.002 (2)	0.003 (3)
C10	0.052 (3)	0.063 (5)	0.056 (3)	−0.005 (3)	−0.002 (3)	0.003 (4)
C11	0.047 (3)	0.069 (4)	0.066 (4)	0.005 (3)	0.004 (3)	0.009 (4)
C12	0.068 (4)	0.045 (4)	0.057 (4)	−0.004 (3)	0.016 (3)	0.009 (3)
C13	0.056 (4)	0.067 (5)	0.066 (4)	−0.003 (4)	−0.001 (3)	−0.008 (4)
C14	0.052 (3)	0.062 (4)	0.061 (3)	0.000 (4)	−0.002 (3)	0.003 (4)

Geometric parameters (Å, º)

Cl—C12	1.754 (6)	C3—C4	1.354 (10)
C6—C1	1.392 (8)	C3—H3A	0.9300
C6—C5	1.398 (8)	C4—C5	1.391 (9)
C6—C7	1.428 (8)	C4—H4A	0.9300
O1—C5	1.345 (7)	C8—C9	1.474 (8)
O1—H	1.06 (7)	C9—C14	1.372 (8)
O2—C7	1.355 (6)	C9—C10	1.394 (7)
O2—N1	1.415 (6)	C10—C11	1.392 (8)
N1—C8	1.300 (7)	C10—H10A	0.9300
N2—C7	1.292 (7)	C11—C12	1.353 (8)
N2—C8	1.367 (7)	C11—H11A	0.9300
C1—C2	1.379 (10)	C12—C13	1.376 (8)
C1—H1B	0.9300	C13—C14	1.393 (9)
C2—C3	1.374 (9)	C13—H13A	0.9300
C2—H2B	0.9300	C14—H14A	0.9300
C1—C6—C5	119.0 (6)	N2—C7—C6	128.3 (5)
C1—C6—C7	122.0 (5)	O2—C7—C6	119.5 (5)
C5—C6—C7	119.0 (5)	N1—C8—N2	114.3 (5)
C5—O1—H	112 (3)	N1—C8—C9	121.3 (5)
C7—O2—N1	106.2 (4)	N2—C8—C9	124.4 (5)
C8—N1—O2	103.4 (4)	C14—C9—C10	119.6 (6)
C7—N2—C8	103.9 (4)	C14—C9—C8	121.1 (5)
C2—C1—C6	120.7 (6)	C10—C9—C8	119.2 (5)
C2—C1—H1B	119.6	C11—C10—C9	119.3 (5)
C6—C1—H1B	119.6	C11—C10—H10A	120.4
C3—C2—C1	119.6 (7)	C9—C10—H10A	120.4
C3—C2—H2B	120.2	C12—C11—C10	119.6 (6)
C1—C2—H2B	120.2	C12—C11—H11A	120.2
C4—C3—C2	120.6 (7)	C10—C11—H11A	120.2
C4—C3—H3A	119.7	C11—C12—C13	122.7 (6)
C2—C3—H3A	119.7	C11—C12—Cl	119.0 (5)
C3—C4—C5	121.1 (6)	C13—C12—Cl	118.3 (5)
C3—C4—H4A	119.4	C12—C13—C14	117.5 (6)
C5—C4—H4A	119.4	C12—C13—H13A	121.3
O1—C5—C4	117.9 (6)	C14—C13—H13A	121.3
O1—C5—C6	123.1 (6)	C9—C14—C13	121.3 (5)
C4—C5—C6	118.9 (6)	C9—C14—H14A	119.4
N2—C7—O2	112.1 (5)	C13—C14—H14A	119.4
C7—O2—N1—C8	−1.1 (5)	C5—C6—C7—O2	176.1 (5)
C5—C6—C1—C2	1.1 (9)	O2—N1—C8—N2	0.6 (6)
C7—C6—C1—C2	178.7 (5)	O2—N1—C8—C9	179.7 (4)
C6—C1—C2—C3	−0.4 (10)	C7—N2—C8—N1	0.2 (7)
C1—C2—C3—C4	0.4 (11)	C7—N2—C8—C9	−178.9 (5)
C2—C3—C4—C5	−1.3 (11)	N1—C8—C9—C14	9.0 (8)
C3—C4—C5—O1	179.2 (6)	N2—C8—C9—C14	−172.0 (6)
C3—C4—C5—C6	2.1 (9)	N1—C8—C9—C10	−173.5 (6)
C1—C6—C5—O1	−178.9 (6)	N2—C8—C9—C10	5.5 (8)
C7—C6—C5—O1	3.5 (9)	C14—C9—C10—C11	−2.4 (9)
C1—C6—C5—C4	−2.0 (8)	C8—C9—C10—C11	−180.0 (5)
C7—C6—C5—C4	−179.6 (5)	C9—C10—C11—C12	1.8 (9)
C8—N2—C7—O2	−1.0 (6)	C10—C11—C12—C13	−1.5 (9)
C8—N2—C7—C6	−177.0 (5)	C10—C11—C12—Cl	179.8 (4)
N1—O2—C7—N2	1.3 (6)	C11—C12—C13—C14	1.8 (9)
N1—O2—C7—C6	177.8 (4)	Cl—C12—C13—C14	−179.5 (5)
C1—C6—C7—N2	174.3 (6)	C10—C9—C14—C13	2.8 (10)
C5—C6—C7—N2	−8.1 (8)	C8—C9—C14—C13	−179.7 (6)
C1—C6—C7—O2	−1.5 (8)	C12—C13—C14—C9	−2.4 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H···N2	1.06 (7)	1.78 (6)	2.680 (6)	139 (5)