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

Yan, X.-C.; Wang, H.-B.; Liu, Z.-Q.

doi:10.1107/S1600536806008142

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

X.-C. Yan, H.-B. Wang and Z.-Q. Liu

The crystal structure of the title compound, C₁₀H₁₀N₂O₂, is characterized by an O—H

N hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008142/bt2010sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008142/bt2010Isup2.hkl Contains datablock I

CCDC reference: 604973

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.053
wR factor = 0.152
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   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

   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
   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: 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: SHELXL97.

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

Crystal data top

C₁₀H₁₀N₂O₂	F(000) = 400
M_r = 190.20	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 7.529 (2) Å	θ = 9–13°
b = 14.307 (3) Å	µ = 0.10 mm⁻¹
c = 8.799 (3) Å	T = 293 K
β = 106.39 (3)°	Block, colourless
V = 909.3 (5) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1242 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 26.0°, θ_min = 2.9°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
T_min = 0.971, T_max = 0.980	l = −10→10
1896 measured reflections	3 standard reflections every 200 reflections
1764 independent reflections	intensity decay: please provide

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.08P)² + 0.3P] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.002
1764 reflections	Δρ_max = 0.14 e Å⁻³
128 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (10)

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.

¹H NMR (CDCl₃): δ 7.92–7.94 (m, 1H), 7.37–7.40 (m, 1H), 7.28–7.32 (m, 2H), 4.94 (s, 2H), 3.46–3.47 (w, H), 2.60–2.61 (s, 3H).

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

	x	y	z	U_iso*/U_eq
O1	0.3216 (2)	0.68819 (11)	1.2124 (2)	0.0559 (5)
O2	0.3893 (3)	0.60569 (12)	1.5756 (2)	0.0607 (5)
N1	0.2464 (3)	0.64625 (14)	1.0624 (2)	0.0540 (6)
N2	0.3906 (2)	0.53988 (12)	1.2415 (2)	0.0415 (5)
C1	0.0278 (4)	0.59033 (19)	0.7579 (3)	0.0590 (7)
H1B	−0.0584	0.5826	0.6550	0.089*
H1C	0.1212	0.6346	0.7517	0.089*
H1D	−0.0365	0.6127	0.8307	0.089*
C2	0.1169 (3)	0.49816 (17)	0.8147 (3)	0.0436 (6)
C3	0.0774 (3)	0.4215 (2)	0.7135 (3)	0.0553 (7)
H3A	−0.0055	0.4289	0.6135	0.066*
C4	0.1564 (4)	0.33503 (19)	0.7559 (3)	0.0599 (7)
H4A	0.1277	0.2855	0.6847	0.072*
C5	0.2780 (4)	0.32227 (17)	0.9038 (3)	0.0538 (6)
H5A	0.3319	0.2641	0.9331	0.065*
C6	0.3193 (3)	0.39597 (15)	1.0078 (3)	0.0463 (6)
H6A	0.4010	0.3870	1.1079	0.056*
C7	0.2409 (3)	0.48431 (15)	0.9664 (2)	0.0390 (5)
C8	0.2904 (3)	0.55843 (15)	1.0875 (3)	0.0383 (5)
C9	0.4033 (3)	0.61996 (15)	1.3100 (3)	0.0426 (5)
C10	0.4909 (4)	0.64440 (18)	1.4796 (3)	0.0556 (7)
H10A	0.6168	0.6207	1.5124	0.067*
H10B	0.4957	0.7118	1.4917	0.067*
H2A	0.4326	0.5436	1.6246	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0594 (11)	0.0394 (9)	0.0614 (11)	0.0045 (8)	0.0049 (8)	−0.0041 (8)
O2	0.0650 (11)	0.0602 (11)	0.0566 (11)	0.0118 (9)	0.0169 (9)	0.0086 (8)
N1	0.0574 (13)	0.0451 (11)	0.0528 (12)	0.0055 (10)	0.0046 (10)	−0.0017 (9)
N2	0.0378 (10)	0.0396 (10)	0.0464 (11)	−0.0001 (8)	0.0111 (8)	0.0016 (8)
C1	0.0507 (14)	0.0727 (18)	0.0508 (14)	0.0079 (13)	0.0096 (12)	0.0135 (13)
C2	0.0325 (11)	0.0550 (14)	0.0453 (12)	−0.0015 (10)	0.0144 (9)	0.0033 (10)
C3	0.0444 (13)	0.0737 (18)	0.0466 (14)	−0.0084 (12)	0.0107 (11)	−0.0049 (13)
C4	0.0595 (16)	0.0584 (16)	0.0628 (17)	−0.0131 (13)	0.0188 (13)	−0.0176 (13)
C5	0.0554 (15)	0.0440 (13)	0.0631 (16)	−0.0019 (11)	0.0186 (12)	−0.0060 (11)
C6	0.0420 (12)	0.0440 (13)	0.0516 (14)	0.0005 (10)	0.0113 (10)	−0.0011 (10)
C7	0.0322 (10)	0.0429 (12)	0.0446 (12)	−0.0042 (9)	0.0152 (9)	0.0009 (9)
C8	0.0310 (10)	0.0387 (11)	0.0455 (12)	0.0001 (9)	0.0114 (9)	0.0042 (10)
C9	0.0347 (11)	0.0396 (12)	0.0533 (13)	−0.0008 (9)	0.0121 (10)	0.0013 (10)
C10	0.0527 (14)	0.0504 (14)	0.0590 (15)	−0.0039 (12)	0.0084 (12)	−0.0087 (12)

Geometric parameters (Å, º) top

O1—C9	1.331 (3)	C3—C4	1.378 (4)
O1—N1	1.414 (3)	C3—H3A	0.9300
O2—C10	1.404 (3)	C4—C5	1.376 (4)
O2—H2A	1.0008	C4—H4A	0.9300
N1—C8	1.302 (3)	C5—C6	1.373 (3)
N2—C9	1.285 (3)	C5—H5A	0.9300
N2—C8	1.378 (3)	C6—C7	1.399 (3)
C1—C2	1.500 (3)	C6—H6A	0.9300
C1—H1B	0.9600	C7—C8	1.475 (3)
C1—H1C	0.9600	C9—C10	1.493 (3)
C1—H1D	0.9600	C10—H10A	0.9700
C2—C3	1.391 (3)	C10—H10B	0.9700
C2—C7	1.411 (3)

C9—O1—N1	106.35 (17)	C6—C5—H5A	120.2
C10—O2—H2A	116.2	C4—C5—H5A	120.2
C8—N1—O1	103.61 (17)	C5—C6—C7	121.4 (2)
C9—N2—C8	103.70 (18)	C5—C6—H6A	119.3
C2—C1—H1B	109.5	C7—C6—H6A	119.3
C2—C1—H1C	109.5	C6—C7—C2	119.4 (2)
H1B—C1—H1C	109.5	C6—C7—C8	117.37 (19)
C2—C1—H1D	109.5	C2—C7—C8	123.2 (2)
H1B—C1—H1D	109.5	N1—C8—N2	113.27 (19)
H1C—C1—H1D	109.5	N1—C8—C7	124.8 (2)
C3—C2—C7	117.4 (2)	N2—C8—C7	121.91 (18)
C3—C2—C1	119.0 (2)	N2—C9—O1	113.1 (2)
C7—C2—C1	123.6 (2)	N2—C9—C10	129.1 (2)
C4—C3—C2	122.5 (2)	O1—C9—C10	117.8 (2)
C4—C3—H3A	118.8	O2—C10—C9	110.3 (2)
C2—C3—H3A	118.8	O2—C10—H10A	109.6
C5—C4—C3	119.7 (2)	C9—C10—H10A	109.6
C5—C4—H4A	120.1	O2—C10—H10B	109.6
C3—C4—H4A	120.1	C9—C10—H10B	109.6
C6—C5—C4	119.6 (2)	H10A—C10—H10B	108.1

C9—O1—N1—C8	0.4 (2)	O1—N1—C8—C7	179.32 (19)
C7—C2—C3—C4	−1.0 (3)	C9—N2—C8—N1	1.0 (2)
C1—C2—C3—C4	178.7 (2)	C9—N2—C8—C7	−179.14 (19)
C2—C3—C4—C5	0.7 (4)	C6—C7—C8—N1	171.9 (2)
C3—C4—C5—C6	0.0 (4)	C2—C7—C8—N1	−9.6 (3)
C4—C5—C6—C7	−0.3 (4)	C6—C7—C8—N2	−7.9 (3)
C5—C6—C7—C2	0.0 (3)	C2—C7—C8—N2	170.60 (19)
C5—C6—C7—C8	178.6 (2)	C8—N2—C9—O1	−0.8 (2)
C3—C2—C7—C6	0.6 (3)	C8—N2—C9—C10	177.7 (2)
C1—C2—C7—C6	−179.0 (2)	N1—O1—C9—N2	0.3 (2)
C3—C2—C7—C8	−177.9 (2)	N1—O1—C9—C10	−178.36 (19)
C1—C2—C7—C8	2.5 (3)	N2—C9—C10—O2	−68.3 (3)
O1—N1—C8—N2	−0.9 (2)	O1—C9—C10—O2	110.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2ⁱ	1.00	1.92	2.858 (3)	154

Symmetry code: (i) −x+1, −y+1, −z+3.

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

Supporting information

Key indicators

checkCIF/PLATON results

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