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

Dang, Y.-Q.; Tian, L.-J.

doi:10.1107/S1600536809007946

organic compounds

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Volume 65| Part 4| April 2009| Page o720

doi:10.1107/S1600536809007946

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

Yan-Qiu Dang ^a ^* and Lai-Jin Tian ^b

^aDepartment of Chemistry and Chemical Engineering, Binzhou University, Binzhou 256600, People's Republic of China, and ^bDepartment of Chemistry, Qufu Normal University, Qufu 273165, People's Republic of China
^*Correspondence e-mail: yanqiudang@163.com

(Received 2 March 2009; accepted 4 March 2009; online 11 March 2009)

In the title Schiff base compound, C₁₁H₁₂N₄O, the molecule 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, molecules are linked into a one-dimensional supramolecular chain by intermolecular 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 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_r = 216.25
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.135
S = 1.01
1196 reflections
146 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Schiff bases play an important role in coordination chemistry and have demonstrated significant biological activity (Ali et al., 2002; Borisova et al., 2007; Maheswari et al., 2006). The title compound, derived from 2-phenyl-2H-1,2,3-triazole-4-carbaldehyde and 2-aminoethanol, is a potential N₃O tetradentate Schiff base ligand. Its crystal structure is described here.

The title molecule (Fig. 1) 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)°. Atoms C9 and N4 are nearly coplanar with the triazole ring; the maximum deviation from the mean plane through these seven atoms is 0.066 (7) Å for C9. The torsion angles C8—C7—C9—N4 and N3—C7—C9—N4 are 8.4 (11) and -173.2 (6)°, respectively. The bond lengths (Allen et al., 1987) and angles of the molecule are within normal ranges. The N4═C9 [1.255 (5) Å] and N4—C10 [1.461 (5) Å] bond distances are comparable to those found in similar Schiff base compounds, such as 2-(2-(2-(4-phenylpiperazinyl)ethoxy)benzylideneamino)ethanol (Nate et al., 1987) and 1,4-bis(2-hydroxy-3-(N-(2-hydroxyethyl)imino)-5-methylbenzyl)piperazine (Yogavel et al., 2003). In the crystal structure, O1—H1···N4 intermolecular hydrogen bonds (Table 1 and Fig. 2), formed between the hydroxyl group and the imino N, link the molecules into a one-dimension supramolecular chain.

Related literature top

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 Schiff bases, see: Nate et al. (1987); Yogavel et al. (2003). For standard bond-length data, see: Allen et al. (1987).

Experimental top

2-Phenyl-2H-1,2,3-triazole-4-carbaldehyde (0.17 g, 1 mmol) and 2-aminoethanol (0.06 g, 1 mmol) were refluxed for 30 min in a methanol solution (15 ml). The reaction mixture was cooled to room temprature and filtered. After allowing the filtrate to stand in air for 3 d, pale yellow plate crystals (yield 76%; mp 346–347 K) were obtained.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed down the a axis. The intermolecular hydrogen bonds are shown as dashed lines.

2-[(E)-(2-Phenyl-2H-1,2,3-triazol-4-yl)methyleneamino]ethanol top

Crystal data top

C₁₁H₁₂N₄O	F(000) = 456
M_r = 216.25	D_x = 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

Data collection top

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

Refinement top

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 = 1.01	w = 1/[σ²(F_o²) + (0.0327P)²] where P = (F_o² + 2F_c²)/3
1196 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₁H₁₂N₄O	V = 1115.8 (8) Å³
M_r = 216.25	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 13.124 (5) Å	µ = 0.09 mm⁻¹
b = 12.770 (5) Å	T = 295 K
c = 6.658 (3) Å	0.12 × 0.07 × 0.03 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	1196 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	596 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.993	R_int = 0.084
5534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	1 restraint
wR(F²) = 0.135	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
1196 reflections	Δρ_min = −0.14 e Å⁻³
146 parameters

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.

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₄O
M_r	216.25
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	295
a, b, c (Å)	13.124 (5), 12.770 (5), 6.658 (3)
V (Å³)	1115.8 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.12 × 0.07 × 0.03

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.989, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5534, 1196, 596
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.135, 1.01
No. of reflections	1196
No. of parameters	146
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4ⁱ	0.82	2.02	2.835 (6)	173.1

Symmetry code: (i) −x+1/2, y, z+1/2.

Acknowledgements

This work was supported by the Key Laboratory of Colloid Interface Chemistry of the Ministry of Education (200707). Binzhou University is also thanked for supporting this work (BZXYQNLG200820).

References

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