2-[(E)-(2-Phenyl-2H-1,2,3-triazol-4-yl)methyl-eneamino]ethanol.

In the title Schiff base compound, C(11)H(12)N(4)O, the mol-ecule adopts a trans configuration about the central C=N bond. The dihedral angle between the phenyl ring and the triazole ring is 14.3 (3)°. In the crystal structure, mol-ecules are linked into a one-dimensional supra-molecular chain by inter-molecular O-H⋯N hydrogen bonding between the hydroxyl group and the imino N atom.

Related literature

For related literature on Schiff bases, see: Ali et al. (2002 ▶); Borisova et al. (2007 ▶); Maheswari et al. (2006 ▶). For the crystal structures of similar n class="Chemical">Schiff bases, see: Nate et al. (1987 ▶); Yogavel et al. (2003 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12N4O

M = 216.25

Orthorhombic,

a = 13.124 (5) Å

b = 12.770 (5) Å

c = 6.658 (3) Å

V = 1115.8 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.12 × 0.07 × 0.03 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.989, T max = 0.993

5534 measured reflections

1196 independent reflections

596 reflections with I > 2σ(I)

R int = 0.084

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.135

S = 1.01

1196 reflections

146 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007946/wn2313sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007946/wn2313Isup2.hkl

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

C11H12N4O	F(000) = 456
Mr = 216.25	Dx = 1.287 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 320 reflections
a = 13.124 (5) Å	θ = 2.2–18.5°
b = 12.770 (5) Å	µ = 0.09 mm−1
c = 6.658 (3) Å	T = 295 K
V = 1115.8 (8) Å3	Plate, pale yellow
Z = 4	0.12 × 0.07 × 0.03 mm

Bruker SMART APEX area-detector diffractometer	1196 independent reflections
Radiation source: fine-focus sealed tube	596 reflections with I > 2σ(I)
graphite	Rint = 0.084
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −16→16
Tmin = 0.989, Tmax = 0.993	k = −13→15
5534 measured reflections	l = −7→8

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0327P)2] where P = (Fo2 + 2Fc2)/3
1196 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.0897 (3)	0.2763 (3)	0.8805 (10)	0.0761 (13)
N2	0.1661 (3)	0.3447 (3)	0.8868 (7)	0.0596 (11)
N3	0.2589 (3)	0.3020 (3)	0.8840 (7)	0.0578 (10)
N4	0.3009 (3)	0.0258 (3)	0.8507 (8)	0.0687 (13)
O1	0.3829 (3)	−0.0715 (3)	1.2273 (8)	0.0842 (13)
H1	0.3311	−0.0391	1.2570	0.126*
C1	0.1492 (4)	0.4541 (4)	0.8940 (10)	0.0680 (14)
C2	0.0539 (5)	0.4918 (4)	0.9368 (10)	0.084 (2)
H2	0.0006	0.4456	0.9619	0.101*
C3	0.0372 (6)	0.5982 (5)	0.9427 (11)	0.103 (3)
H3	−0.0274	0.6241	0.9718	0.123*
C4	0.1147 (7)	0.6647 (5)	0.9060 (11)	0.113 (3)
H4	0.1035	0.7365	0.9139	0.136*
C5	0.2086 (6)	0.6287 (4)	0.8579 (11)	0.107 (2)
H5	0.2605	0.6758	0.8274	0.128*
C6	0.2278 (5)	0.5209 (4)	0.8539 (9)	0.0877 (19)
H6	0.2925	0.4954	0.8247	0.105*
C7	0.2401 (3)	0.2000 (3)	0.8766 (9)	0.0602 (13)
C8	0.1364 (3)	0.1845 (4)	0.8733 (11)	0.0720 (15)
H8	0.1041	0.1197	0.8669	0.086*
C9	0.3212 (4)	0.1209 (4)	0.8771 (10)	0.0673 (14)
H9	0.3884	0.1414	0.8972	0.081*
C10	0.3852 (3)	−0.0487 (4)	0.8635 (14)	0.0854 (19)
H10A	0.4489	−0.0112	0.8791	0.103*
H10B	0.3888	−0.0894	0.7408	0.103*
C11	0.3691 (4)	−0.1209 (4)	1.0410 (13)	0.077 (2)
H11A	0.3006	−0.1491	1.0349	0.093*
H11B	0.4163	−0.1791	1.0308	0.093*

	U11	U22	U33	U12	U13	U23
N1	0.066 (2)	0.051 (2)	0.111 (4)	−0.004 (2)	0.003 (4)	0.007 (4)
N2	0.076 (3)	0.046 (2)	0.057 (3)	−0.001 (2)	0.002 (3)	0.005 (3)
N3	0.071 (2)	0.052 (2)	0.051 (3)	−0.0108 (19)	−0.002 (3)	0.001 (3)
N4	0.063 (2)	0.054 (2)	0.089 (4)	0.005 (2)	0.012 (3)	0.009 (3)
O1	0.070 (3)	0.066 (3)	0.117 (4)	0.0067 (19)	−0.014 (2)	−0.001 (3)
C1	0.100 (4)	0.052 (3)	0.053 (4)	−0.004 (3)	0.008 (4)	−0.006 (4)
C2	0.105 (4)	0.062 (4)	0.086 (6)	0.009 (3)	0.001 (4)	−0.005 (3)
C3	0.156 (7)	0.061 (4)	0.092 (6)	0.023 (4)	−0.005 (5)	0.002 (4)
C4	0.207 (9)	0.055 (4)	0.077 (6)	0.013 (5)	0.013 (7)	−0.010 (4)
C5	0.181 (8)	0.057 (4)	0.083 (6)	−0.028 (4)	0.043 (6)	−0.011 (4)
C6	0.132 (5)	0.056 (3)	0.075 (5)	−0.023 (3)	0.020 (5)	−0.004 (4)
C7	0.064 (3)	0.050 (3)	0.066 (4)	−0.008 (2)	−0.001 (4)	0.013 (3)
C8	0.068 (3)	0.047 (3)	0.101 (5)	0.000 (2)	−0.012 (5)	0.012 (4)
C9	0.063 (3)	0.066 (3)	0.073 (4)	−0.007 (2)	−0.004 (4)	0.014 (5)
C10	0.069 (3)	0.064 (3)	0.124 (6)	0.018 (3)	0.017 (5)	−0.011 (5)
C11	0.055 (3)	0.045 (3)	0.132 (7)	0.012 (3)	0.010 (4)	0.007 (5)

N1—C8	1.324 (5)	C4—C5	1.354 (8)
N1—N2	1.330 (5)	C4—H4	0.9300
N2—N3	1.336 (5)	C5—C6	1.400 (7)
N2—C1	1.415 (6)	C5—H5	0.9300
N3—C7	1.327 (5)	C6—H6	0.9300
N4—C9	1.255 (5)	C7—C8	1.376 (6)
N4—C10	1.461 (5)	C7—C9	1.468 (6)
O1—C11	1.403 (8)	C8—H8	0.9300
O1—H1	0.8200	C9—H9	0.9300
C1—C6	1.365 (7)	C10—C11	1.514 (9)
C1—C2	1.371 (7)	C10—H10A	0.9700
C2—C3	1.377 (7)	C10—H10B	0.9700
C2—H2	0.9300	C11—H11A	0.9700
C3—C4	1.347 (9)	C11—H11B	0.9700
C3—H3	0.9300
C8—N1—N2	103.5 (4)	C1—C6—H6	120.8
N1—N2—N3	114.8 (3)	C5—C6—H6	120.8
N1—N2—C1	122.1 (4)	N3—C7—C8	109.0 (4)
N3—N2—C1	123.1 (4)	N3—C7—C9	122.7 (4)
C7—N3—N2	103.4 (3)	C8—C7—C9	128.3 (4)
C9—N4—C10	117.4 (4)	N1—C8—C7	109.3 (4)
C11—O1—H1	109.5	N1—C8—H8	125.4
C6—C1—C2	120.8 (5)	C7—C8—H8	125.4
C6—C1—N2	119.5 (5)	N4—C9—C7	120.7 (4)
C2—C1—N2	119.7 (5)	N4—C9—H9	119.6
C1—C2—C3	119.8 (6)	C7—C9—H9	119.6
C1—C2—H2	120.1	N4—C10—C11	109.7 (5)
C3—C2—H2	120.1	N4—C10—H10A	109.7
C4—C3—C2	119.8 (7)	C11—C10—H10A	109.7
C4—C3—H3	120.1	N4—C10—H10B	109.7
C2—C3—H3	120.1	C11—C10—H10B	109.7
C3—C4—C5	121.1 (6)	H10A—C10—H10B	108.2
C3—C4—H4	119.4	O1—C11—C10	113.5 (5)
C5—C4—H4	119.4	O1—C11—H11A	108.9
C4—C5—C6	120.1 (6)	C10—C11—H11A	108.9
C4—C5—H5	119.9	O1—C11—H11B	108.9
C6—C5—H5	119.9	C10—C11—H11B	108.9
C1—C6—C5	118.3 (6)	H11A—C11—H11B	107.7
C8—N1—N2—N3	0.0 (8)	C2—C1—C6—C5	0.1 (10)
C8—N1—N2—C1	179.4 (6)	N2—C1—C6—C5	178.7 (6)
N1—N2—N3—C7	−0.3 (7)	C4—C5—C6—C1	1.8 (11)
C1—N2—N3—C7	−179.8 (5)	N2—N3—C7—C8	0.5 (7)
N1—N2—C1—C6	−165.0 (6)	N2—N3—C7—C9	−178.2 (5)
N3—N2—C1—C6	14.4 (9)	N2—N1—C8—C7	0.4 (8)
N1—N2—C1—C2	13.6 (10)	N3—C7—C8—N1	−0.6 (8)
N3—N2—C1—C2	−166.9 (6)	C9—C7—C8—N1	178.0 (6)
C6—C1—C2—C3	−1.0 (11)	C10—N4—C9—C7	−176.9 (6)
N2—C1—C2—C3	−179.6 (6)	N3—C7—C9—N4	−173.2 (6)
C1—C2—C3—C4	0.1 (11)	C8—C7—C9—N4	8.4 (11)
C2—C3—C4—C5	1.8 (12)	C9—N4—C10—C11	115.1 (7)
C3—C4—C5—C6	−2.8 (12)	N4—C10—C11—O1	−71.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4i	0.82	2.02	2.835 (6)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N4i	0.82	2.02	2.835 (6)	173

Symmetry code: (i) .