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

In the approximately planar molecule of the title compound, C₁₅H₁₂N₂O₂, which is a derivative of oxadiazole, 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) = 0.008 Å
• R factor = 0.063
• wR factor = 0.181
• Data-to-parameter ratio = 7.9

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) .....       7.91
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               1360
           Count of symmetry unique reflns         1364
           Completeness (_total/calc)             99.71%
           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         no
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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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-Methylphenyl)-1,2,4-oxadiazol-5-yl]phenol

Crystal data

C15H12N2O2	F(000) = 264
Mr = 252.27	Dx = 1.343 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 6.5110 (13) Å	θ = 9–12°
b = 5.172 (1) Å	µ = 0.09 mm^−1
c = 18.763 (4) Å	T = 293 K
β = 99.14 (3)°	Block, colourless
V = 623.8 (2) Å^3	0.30 × 0.10 × 0.10 mm
Z = 2

Data collection

Enraf–Nonius CAD-4 diffractometer	900 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 26.0°, θmin = 1.1°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→6
Tmin = 0.973, Tmax = 0.991	l = −23→22
1483 measured reflections	3 standard reflections every 200 reflections
1360 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.181	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.099P)^2] where P = (Fo^2 + 2Fc^2)/3
1360 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.21 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

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
O1	0.3517 (5)	1.0967 (8)	0.2605 (2)	0.0667 (11)
O2	0.9481 (6)	1.2325 (9)	0.3728 (2)	0.0789 (13)
H2A	0.9092	1.1246	0.3416	0.118*
N1	0.3661 (6)	0.8946 (10)	0.2106 (2)	0.0657 (13)
N2	0.6824 (6)	0.9897 (8)	0.2723 (2)	0.0515 (11)
C1	0.9121 (10)	0.0519 (13)	0.0584 (3)	0.084 (2)
H1B	0.8061	−0.0175	0.0220	0.126*
H1C	0.9686	−0.0838	0.0905	0.126*
H1D	1.0208	0.1260	0.0358	0.126*
C2	0.8201 (8)	0.2562 (11)	0.1000 (3)	0.0584 (14)
C3	0.9425 (8)	0.3869 (12)	0.1558 (3)	0.0646 (15)
H3A	1.0830	0.3461	0.1671	0.078*
C4	0.8602 (8)	0.5773 (11)	0.1952 (3)	0.0616 (15)
H4A	0.9449	0.6627	0.2324	0.074*
C5	0.6521 (7)	0.6386 (11)	0.1787 (3)	0.0499 (12)
C6	0.5298 (8)	0.5093 (12)	0.1238 (3)	0.0637 (15)
H6A	0.3891	0.5491	0.1128	0.076*
C7	0.6130 (9)	0.3208 (13)	0.0845 (3)	0.0697 (17)
H7A	0.5277	0.2368	0.0471	0.084*
C8	0.5640 (7)	0.8413 (10)	0.2205 (2)	0.0499 (12)
C9	0.5446 (7)	1.1411 (11)	0.2946 (3)	0.0533 (13)
C10	0.5832 (8)	1.3408 (10)	0.3479 (3)	0.0557 (13)
C11	0.4232 (9)	1.4999 (11)	0.3631 (3)	0.0666 (16)
H11A	0.2889	1.4756	0.3385	0.080*
C12	0.4603 (11)	1.6904 (13)	0.4135 (4)	0.0770 (18)
H12A	0.3530	1.7981	0.4226	0.092*
C13	0.6590 (12)	1.7223 (15)	0.4511 (3)	0.0830 (19)
H13A	0.6837	1.8494	0.4865	0.100*
C14	0.8190 (11)	1.5718 (14)	0.4375 (3)	0.0809 (19)
H14A	0.9524	1.5983	0.4625	0.097*
C15	0.7820 (8)	1.3768 (11)	0.3855 (3)	0.0598 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.057 (2)	0.059 (2)	0.082 (2)	0.003 (2)	0.0037 (18)	−0.004 (2)
O2	0.068 (2)	0.069 (3)	0.093 (3)	−0.008 (2)	−0.009 (2)	−0.014 (2)
N1	0.056 (3)	0.059 (3)	0.080 (3)	−0.002 (2)	0.004 (2)	−0.009 (3)
N2	0.049 (2)	0.045 (2)	0.060 (2)	−0.006 (2)	0.0055 (19)	0.006 (2)
C1	0.114 (5)	0.055 (4)	0.088 (4)	0.012 (4)	0.033 (4)	0.000 (4)
C2	0.070 (3)	0.039 (3)	0.067 (3)	0.002 (3)	0.014 (3)	0.013 (3)
C3	0.056 (3)	0.060 (4)	0.077 (4)	0.004 (3)	0.008 (3)	0.015 (4)
C4	0.057 (3)	0.052 (3)	0.074 (3)	−0.005 (3)	0.004 (2)	0.007 (3)
C5	0.051 (3)	0.044 (3)	0.054 (3)	−0.007 (3)	0.004 (2)	0.010 (3)
C6	0.056 (3)	0.063 (4)	0.069 (3)	−0.003 (3)	0.000 (3)	−0.003 (3)
C7	0.078 (4)	0.066 (4)	0.064 (3)	−0.011 (4)	0.004 (3)	−0.004 (3)
C8	0.048 (3)	0.044 (3)	0.057 (3)	−0.004 (3)	0.006 (2)	0.007 (3)
C9	0.054 (3)	0.047 (3)	0.058 (3)	−0.008 (3)	0.007 (2)	0.004 (3)
C10	0.070 (3)	0.044 (3)	0.057 (3)	−0.010 (3)	0.019 (2)	0.005 (3)
C11	0.078 (4)	0.049 (3)	0.078 (4)	−0.009 (3)	0.030 (3)	0.005 (3)
C12	0.097 (5)	0.053 (4)	0.090 (4)	−0.002 (4)	0.044 (4)	0.001 (4)
C13	0.119 (6)	0.060 (4)	0.074 (4)	−0.004 (5)	0.030 (4)	−0.006 (4)
C14	0.104 (5)	0.065 (4)	0.068 (4)	−0.023 (4)	−0.004 (3)	0.001 (4)
C15	0.070 (3)	0.048 (3)	0.061 (3)	−0.010 (3)	0.008 (3)	0.002 (3)

Geometric parameters (Å, º)

O1—C9	1.336 (6)	C5—C6	1.372 (7)
O1—N1	1.416 (6)	C5—C8	1.478 (7)
O2—C15	1.365 (6)	C6—C7	1.384 (8)
O2—H2A	0.8200	C6—H6A	0.9300
N1—C8	1.302 (6)	C7—H7A	0.9300
N2—C9	1.309 (6)	C9—C10	1.432 (7)
N2—C8	1.375 (6)	C10—C15	1.385 (7)
C1—C2	1.495 (8)	C10—C11	1.392 (7)
C1—H1B	0.9600	C11—C12	1.360 (8)
C1—H1C	0.9600	C11—H11A	0.9300
C1—H1D	0.9600	C12—C13	1.382 (9)
C2—C7	1.375 (8)	C12—H12A	0.9300
C2—C3	1.386 (8)	C13—C14	1.357 (9)
C3—C4	1.389 (8)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.396 (9)
C4—C5	1.378 (6)	C14—H14A	0.9300
C4—H4A	0.9300
C9—O1—N1	106.7 (4)	C2—C7—H7A	119.6
C15—O2—H2A	109.5	C6—C7—H7A	119.6
C8—N1—O1	103.3 (4)	N1—C8—N2	114.4 (5)
C9—N2—C8	103.0 (4)	N1—C8—C5	122.2 (5)
C2—C1—H1B	109.5	N2—C8—C5	123.3 (4)
C2—C1—H1C	109.5	N2—C9—O1	112.6 (5)
H1B—C1—H1C	109.5	N2—C9—C10	127.0 (4)
C2—C1—H1D	109.5	O1—C9—C10	120.4 (5)
H1B—C1—H1D	109.5	C15—C10—C11	119.1 (5)
H1C—C1—H1D	109.5	C15—C10—C9	119.9 (5)
C7—C2—C3	117.9 (5)	C11—C10—C9	121.0 (5)
C7—C2—C1	121.5 (6)	C12—C11—C10	121.0 (6)
C3—C2—C1	120.6 (5)	C12—C11—H11A	119.5
C2—C3—C4	121.5 (5)	C10—C11—H11A	119.5
C2—C3—H3A	119.2	C11—C12—C13	119.3 (7)
C4—C3—H3A	119.2	C11—C12—H12A	120.3
C5—C4—C3	119.5 (5)	C13—C12—H12A	120.3
C5—C4—H4A	120.2	C14—C13—C12	121.3 (7)
C3—C4—H4A	120.2	C14—C13—H13A	119.4
C6—C5—C4	119.2 (5)	C12—C13—H13A	119.4
C6—C5—C8	121.1 (4)	C13—C14—C15	119.6 (6)
C4—C5—C8	119.7 (5)	C13—C14—H14A	120.2
C5—C6—C7	121.0 (5)	C15—C14—H14A	120.2
C5—C6—H6A	119.5	O2—C15—C10	122.7 (5)
C7—C6—H6A	119.5	O2—C15—C14	117.6 (5)
C2—C7—C6	120.8 (5)	C10—C15—C14	119.7 (6)
C9—O1—N1—C8	0.1 (5)	C8—N2—C9—O1	0.0 (5)
C7—C2—C3—C4	0.1 (8)	C8—N2—C9—C10	−178.5 (5)
C1—C2—C3—C4	−180.0 (5)	N1—O1—C9—N2	−0.1 (5)
C2—C3—C4—C5	0.0 (8)	N1—O1—C9—C10	178.6 (4)
C3—C4—C5—C6	0.2 (7)	N2—C9—C10—C15	−4.8 (7)
C3—C4—C5—C8	−179.9 (4)	O1—C9—C10—C15	176.8 (5)
C4—C5—C6—C7	−0.6 (8)	N2—C9—C10—C11	175.6 (5)
C8—C5—C6—C7	179.6 (5)	O1—C9—C10—C11	−2.8 (7)
C3—C2—C7—C6	−0.4 (8)	C15—C10—C11—C12	0.7 (7)
C1—C2—C7—C6	179.6 (5)	C9—C10—C11—C12	−179.7 (5)
C5—C6—C7—C2	0.7 (8)	C10—C11—C12—C13	−1.4 (8)
O1—N1—C8—N2	−0.1 (5)	C11—C12—C13—C14	1.8 (10)
O1—N1—C8—C5	−179.8 (4)	C12—C13—C14—C15	−1.4 (10)
C9—N2—C8—N1	0.1 (6)	C11—C10—C15—O2	−178.7 (5)
C9—N2—C8—C5	179.7 (4)	C9—C10—C15—O2	1.7 (7)
C6—C5—C8—N1	4.7 (7)	C11—C10—C15—C14	−0.4 (7)
C4—C5—C8—N1	−175.2 (5)	C9—C10—C15—C14	180.0 (5)
C6—C5—C8—N2	−174.9 (5)	C13—C14—C15—O2	179.1 (5)
C4—C5—C8—N2	5.2 (7)	C13—C14—C15—C10	0.7 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82	1.94	2.663 (5)	147