2-[(E)-(3,4-Dimethyl-isoxazol-5-yl)imino-meth-yl]phenol.

The title compound, C(12)H(12)N(2)O(2), has been synthesized by the reaction of 5-amino-3,4-dimethyl-isoxazole and salicyladehyde. The mol-ecule adopts an E configuration about the central C=N double bond. The dihedral angle between the isoxazole and phenyl rings is 4.2 (2)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. The crystal studied was a non-merohedral twin with a domain ratio of 0.834 (4):0.166 (4).

Related literature

For background to the biological and pharmacological properties of oxazole derivatives, see: Spinelli (1999 ▶); Conti et al. (1998 ▶); Mishra et al. (1998 ▶); Ko et al. (1998 ▶); Kang et al. (2000 ▶); Huang & Chen (2005 ▶). For details of hydrogen bonding and hydrogen-bond motifs, see: Jeffrey & Saenger (1991 ▶); Bernstein et al. (1995 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C12H12N2O2

M = 216.24

Triclinic,

a = 5.3475 (14) Å

b = 8.615 (2) Å

c = 12.321 (3) Å

α = 103.696 (5)°

β = 91.486 (5)°

γ = 94.059 (5)°

V = 549.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.56 × 0.14 × 0.08 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.951, T max = 0.993

2467 measured reflections

2467 independent reflections

1946 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.203

S = 1.06

2467 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008160/sj2738sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008160/sj2738Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H12N2O2	Z = 2
Mr = 216.24	F(000) = 228
Triclinic, P1	Dx = 1.307 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3475 (14) Å	Cell parameters from 2862 reflections
b = 8.615 (2) Å	θ = 2.4–29.7°
c = 12.321 (3) Å	µ = 0.09 mm−1
α = 103.696 (5)°	T = 100 K
β = 91.486 (5)°	Plate, yellow
γ = 94.059 (5)°	0.56 × 0.14 × 0.08 mm
V = 549.6 (2) Å3

Bruker APEX DUO CCD area-detector diffractometer	2467 independent reflections
Radiation source: fine-focus sealed tube	1946 reflections with I > 2σ(I)
graphite	Rint = 0.0000
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.951, Tmax = 0.993	k = −11→10
2467 measured reflections	l = −6→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0657P)2 + 1.1217P] where P = (Fo2 + 2Fc2)/3
2467 reflections	(Δ/σ)max = 0.001
152 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
O1	1.0387 (4)	1.1305 (2)	0.41739 (17)	0.0228 (5)
O2	0.6135 (4)	0.7350 (3)	0.08828 (18)	0.0262 (5)
N1	0.8330 (5)	0.9521 (3)	0.2591 (2)	0.0194 (5)
N2	1.2481 (5)	1.2478 (3)	0.4414 (2)	0.0252 (6)
C1	0.2930 (5)	0.7387 (3)	0.3499 (3)	0.0201 (6)
H1A	0.3082	0.7892	0.4256	0.024*
C2	0.0960 (5)	0.6240 (3)	0.3108 (3)	0.0221 (6)
H2A	−0.0224	0.5990	0.3593	0.026*
C3	0.0782 (6)	0.5468 (4)	0.1976 (3)	0.0249 (7)
H3A	−0.0529	0.4691	0.1710	0.030*
C4	0.2512 (6)	0.5831 (4)	0.1235 (3)	0.0250 (7)
H4A	0.2362	0.5296	0.0484	0.030*
C5	0.4491 (5)	0.7008 (3)	0.1626 (2)	0.0199 (6)
C6	0.4711 (5)	0.7802 (3)	0.2771 (2)	0.0186 (6)
C7	0.6723 (5)	0.9024 (3)	0.3225 (2)	0.0191 (6)
H7A	0.6859	0.9462	0.3992	0.023*
C8	1.0225 (5)	1.0682 (3)	0.3052 (2)	0.0176 (6)
C9	1.2091 (5)	1.1366 (3)	0.2539 (2)	0.0192 (6)
C10	1.3428 (5)	1.2479 (3)	0.3446 (2)	0.0195 (6)
C11	1.2629 (6)	1.1010 (4)	0.1327 (3)	0.0276 (7)
H11A	1.1457	1.0163	0.0921	0.041*
H11C	1.4305	1.0685	0.1229	0.041*
H11D	1.2470	1.1953	0.1051	0.041*
C12	1.5687 (5)	1.3582 (4)	0.3386 (3)	0.0243 (7)
H12A	1.6191	1.4202	0.4124	0.036*
H12D	1.5285	1.4287	0.2920	0.036*
H12B	1.7034	1.2963	0.3075	0.036*
H1O2	0.722 (11)	0.820 (7)	0.132 (5)	0.080 (18)*

	U11	U22	U33	U12	U13	U23
O1	0.0194 (11)	0.0238 (11)	0.0233 (11)	−0.0060 (8)	0.0019 (8)	0.0042 (8)
O2	0.0250 (12)	0.0281 (11)	0.0232 (11)	−0.0040 (9)	0.0061 (9)	0.0028 (9)
N1	0.0170 (12)	0.0148 (11)	0.0261 (13)	0.0009 (9)	0.0020 (9)	0.0041 (9)
N2	0.0207 (13)	0.0246 (13)	0.0290 (14)	−0.0061 (10)	−0.0003 (10)	0.0062 (10)
C1	0.0155 (14)	0.0176 (13)	0.0270 (15)	0.0054 (10)	0.0036 (11)	0.0036 (11)
C2	0.0152 (14)	0.0204 (14)	0.0318 (16)	0.0021 (11)	0.0054 (11)	0.0078 (12)
C3	0.0159 (14)	0.0225 (14)	0.0353 (17)	−0.0013 (11)	−0.0012 (12)	0.0063 (12)
C4	0.0247 (16)	0.0227 (15)	0.0246 (15)	−0.0006 (12)	−0.0007 (12)	0.0004 (12)
C5	0.0164 (14)	0.0194 (14)	0.0242 (14)	0.0026 (11)	0.0021 (11)	0.0052 (11)
C6	0.0154 (13)	0.0155 (13)	0.0256 (14)	0.0033 (10)	0.0019 (11)	0.0054 (11)
C7	0.0199 (14)	0.0158 (13)	0.0216 (14)	0.0058 (11)	0.0019 (11)	0.0034 (10)
C8	0.0140 (13)	0.0163 (13)	0.0237 (14)	0.0051 (10)	0.0029 (10)	0.0056 (10)
C9	0.0159 (13)	0.0169 (13)	0.0262 (15)	0.0037 (10)	0.0033 (11)	0.0074 (11)
C10	0.0136 (13)	0.0169 (13)	0.0296 (15)	0.0038 (10)	0.0020 (11)	0.0079 (11)
C11	0.0272 (16)	0.0291 (16)	0.0260 (16)	0.0009 (13)	0.0080 (12)	0.0055 (12)
C12	0.0137 (13)	0.0215 (14)	0.0392 (17)	0.0005 (11)	0.0038 (12)	0.0100 (12)

O1—C8	1.357 (3)	C4—H4A	0.9300
O1—N2	1.429 (3)	C5—C6	1.412 (4)
O2—C5	1.353 (4)	C6—C7	1.452 (4)
O2—H1O2	0.95 (6)	C7—H7A	0.9300
N1—C7	1.293 (4)	C8—C9	1.367 (4)
N1—C8	1.381 (4)	C9—C10	1.426 (4)
N2—C10	1.308 (4)	C9—C11	1.491 (4)
C1—C2	1.385 (4)	C10—C12	1.498 (4)
C1—C6	1.410 (4)	C11—H11A	0.9600
C1—H1A	0.9300	C11—H11C	0.9600
C2—C3	1.394 (4)	C11—H11D	0.9600
C2—H2A	0.9300	C12—H12A	0.9600
C3—C4	1.387 (4)	C12—H12D	0.9600
C3—H3A	0.9300	C12—H12B	0.9600
C4—C5	1.404 (4)
C8—O1—N2	107.7 (2)	N1—C7—H7A	119.1
C5—O2—H1O2	103 (3)	C6—C7—H7A	119.1
C7—N1—C8	120.3 (2)	O1—C8—C9	110.8 (2)
C10—N2—O1	105.3 (2)	O1—C8—N1	119.7 (2)
C2—C1—C6	121.2 (3)	C9—C8—N1	129.5 (3)
C2—C1—H1A	119.4	C8—C9—C10	103.2 (3)
C6—C1—H1A	119.4	C8—C9—C11	128.4 (3)
C1—C2—C3	118.9 (3)	C10—C9—C11	128.4 (3)
C1—C2—H2A	120.6	N2—C10—C9	112.9 (3)
C3—C2—H2A	120.6	N2—C10—C12	119.8 (3)
C4—C3—C2	121.6 (3)	C9—C10—C12	127.3 (3)
C4—C3—H3A	119.2	C9—C11—H11A	109.5
C2—C3—H3A	119.2	C9—C11—H11C	109.5
C3—C4—C5	119.7 (3)	H11A—C11—H11C	109.5
C3—C4—H4A	120.2	C9—C11—H11D	109.5
C5—C4—H4A	120.2	H11A—C11—H11D	109.5
O2—C5—C4	118.4 (3)	H11C—C11—H11D	109.5
O2—C5—C6	121.9 (3)	C10—C12—H12A	109.5
C4—C5—C6	119.6 (3)	C10—C12—H12D	109.5
C1—C6—C5	119.0 (3)	H12A—C12—H12D	109.5
C1—C6—C7	118.8 (3)	C10—C12—H12B	109.5
C5—C6—C7	122.2 (3)	H12A—C12—H12B	109.5
N1—C7—C6	121.8 (3)	H12D—C12—H12B	109.5
C8—O1—N2—C10	−0.3 (3)	N2—O1—C8—C9	0.3 (3)
C6—C1—C2—C3	1.3 (4)	N2—O1—C8—N1	−179.4 (2)
C1—C2—C3—C4	−0.6 (5)	C7—N1—C8—O1	−0.3 (4)
C2—C3—C4—C5	−0.3 (5)	C7—N1—C8—C9	−179.9 (3)
C3—C4—C5—O2	−179.3 (3)	O1—C8—C9—C10	−0.2 (3)
C3—C4—C5—C6	0.5 (4)	N1—C8—C9—C10	179.4 (3)
C2—C1—C6—C5	−1.1 (4)	O1—C8—C9—C11	178.7 (3)
C2—C1—C6—C7	179.4 (3)	N1—C8—C9—C11	−1.7 (5)
O2—C5—C6—C1	180.0 (3)	O1—N2—C10—C9	0.1 (3)
C4—C5—C6—C1	0.2 (4)	O1—N2—C10—C12	−179.8 (2)
O2—C5—C6—C7	−0.5 (4)	C8—C9—C10—N2	0.0 (3)
C4—C5—C6—C7	179.7 (3)	C11—C9—C10—N2	−178.9 (3)
C8—N1—C7—C6	−179.7 (2)	C8—C9—C10—C12	180.0 (3)
C1—C6—C7—N1	−176.1 (3)	C11—C9—C10—C12	1.1 (5)
C5—C6—C7—N1	4.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1	1.00 (9)	1.71 (8)	2.648 (5)	154 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N1	1.00 (9)	1.71 (8)	2.648 (5)	154 (8)