(E)-Benz-yl(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth-oxy}benzyl-idene)amine.

The triazole ring of the title compound, C20H20N4O, is normal to the central benzene ring, making a dihedral angle of 90.0 (3)°, and forms a dihedral angle of 69.2 (3)° with the terminal phenyl ring. The dihedral angle between the phenyl and benzene rings is 88.2 (3)°. The atoms of the terminal propenyl group are disordered over two sets of sites, with a site-occupancy ratio of 0.663 (13):0.337 (13). In the crystal, C-H⋯N contacts lead to the formation of a layer structure extending parallel to (011). Two weak C-H⋯π inter-actions are also observed.

Related literature

For background to the importance of Schiff bases and triazole derivatives and their uses, see: Calligaris & Randaccio (1987 ▶); Dikusar & Kozlov (2006 ▶); Macho et al. (2004 ▶); Yap & Weinreb (2006 ▶); Yu et al. (2006 ▶). For similar structures, see: Akkurt et al. (2013a ▶,b ▶).

Experimental

Crystal data

C20H20N4O

M = 332.40

Monoclinic,

a = 8.5873 (9) Å

b = 20.0601 (13) Å

c = 10.7450 (9) Å

β = 97.241 (8)°

V = 1836.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.57 × 0.24 × 0.05 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.971, T max = 0.996

10252 measured reflections

3236 independent reflections

981 reflections with I > 2σ(I)

R int = 0.137

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.117

S = 0.93

3236 reflections

236 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.11 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814002645/sj5391sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002645/sj5391Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002645/sj5391Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H20N4O	F(000) = 704
Mr = 332.40	Dx = 1.202 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4967 reflections
a = 8.5873 (9) Å	θ = 1.9–27.9°
b = 20.0601 (13) Å	µ = 0.08 mm−1
c = 10.7450 (9) Å	T = 296 K
β = 97.241 (8)°	Prism, colourless
V = 1836.2 (3) Å3	0.57 × 0.24 × 0.05 mm
Z = 4

Stoe IPDS 2 diffractometer	3236 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	981 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.137
Detector resolution: 6.67 pixels mm-1	θmax = 25.0°, θmin = 2.0°
ω scans	h = −9→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −23→23
Tmin = 0.971, Tmax = 0.996	l = −12→12
10252 measured reflections

Refinement on F2	6 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.079	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0181P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
3236 reflections	Δρmax = 0.16 e Å−3
236 parameters	Δρmin = −0.11 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
O1	0.3201 (4)	0.56064 (18)	0.0649 (3)	0.0860 (16)
N1	0.2214 (5)	0.2770 (2)	0.3186 (4)	0.089 (2)
N2	0.2721 (5)	0.6732 (2)	−0.1458 (5)	0.091 (2)
N3	0.3496 (6)	0.7255 (3)	−0.1800 (4)	0.092 (2)
N4	0.4179 (5)	0.7540 (2)	−0.0749 (5)	0.0762 (17)
C1	0.0466 (7)	0.1614 (3)	0.1724 (7)	0.092 (3)
C2	0.0451 (9)	0.1104 (4)	0.0881 (6)	0.114 (3)
C3	0.1458 (10)	0.0586 (4)	0.1125 (9)	0.125 (4)
C4	0.2454 (8)	0.0562 (4)	0.2212 (9)	0.127 (4)
C5	0.2463 (8)	0.1079 (4)	0.3075 (6)	0.104 (3)
C6	0.1454 (7)	0.1609 (3)	0.2823 (6)	0.075 (3)
C7	0.1495 (7)	0.2187 (3)	0.3719 (5)	0.099 (3)
C8	0.1315 (6)	0.3256 (3)	0.2899 (5)	0.082 (3)
C9	0.1839 (7)	0.3873 (3)	0.2328 (5)	0.075 (2)
C10	0.3292 (6)	0.3939 (3)	0.1924 (5)	0.079 (2)
C11	0.3695 (6)	0.4523 (3)	0.1362 (5)	0.077 (2)
C12	0.2673 (6)	0.5053 (3)	0.1221 (5)	0.074 (2)
C13	0.1217 (6)	0.4994 (3)	0.1635 (5)	0.084 (3)
C14	0.0817 (6)	0.4405 (3)	0.2180 (5)	0.084 (2)
C15	0.2156 (6)	0.6170 (3)	0.0470 (5)	0.090 (3)
C16	0.2921 (6)	0.6707 (3)	−0.0195 (6)	0.074 (2)
C17	0.3832 (6)	0.7217 (3)	0.0260 (5)	0.082 (3)
C18B	0.512 (2)	0.8153 (7)	−0.072 (2)	0.090 (4)	0.663 (13)
C19B	0.4081 (17)	0.8751 (6)	−0.0933 (16)	0.112 (6)	0.663 (13)
C20B	0.415 (4)	0.9226 (11)	−0.0118 (19)	0.174 (9)	0.663 (13)
C20A	0.382 (8)	0.918 (2)	−0.077 (4)	0.174 (9)	0.337 (13)
C18A	0.503 (6)	0.8150 (14)	−0.104 (4)	0.090 (4)	0.337 (13)
C19A	0.458 (3)	0.8683 (12)	−0.015 (3)	0.112 (6)	0.337 (13)
H2	−0.02440	0.11120	0.01440	0.1370*
H5	0.31470	0.10670	0.38190	0.1250*
H3	0.14660	0.02430	0.05430	0.1500*
H4	0.31270	0.02010	0.23780	0.1530*
H1	−0.02120	0.19720	0.15450	0.1100*
H10	0.40050	0.35880	0.20280	0.0950*
H11	0.46700	0.45590	0.10770	0.0930*
H13	0.05130	0.53490	0.15470	0.1010*
H14	−0.01650	0.43660	0.24520	0.1010*
H15A	0.19210	0.63320	0.12760	0.1080*
H15B	0.11790	0.60380	−0.00210	0.1080*
H17	0.41500	0.73210	0.10960	0.0990*
H18C	0.58140	0.81320	−0.13650	0.1080*	0.663 (13)
H18D	0.57620	0.81910	0.00870	0.1080*	0.663 (13)
H19B	0.33780	0.87810	−0.16630	0.1340*	0.663 (13)
H20C	0.48460	0.92000	0.06150	0.2100*	0.663 (13)
H20D	0.34920	0.95950	−0.02640	0.2100*	0.663 (13)
H7A	0.04360	0.22950	0.38750	0.1180*
H7B	0.20970	0.20660	0.45120	0.1180*
H8	0.02760	0.32260	0.30530	0.0980*
H18A	0.47240	0.82830	−0.19040	0.1080*	0.337 (13)
H18B	0.61520	0.80750	−0.09120	0.1080*	0.337 (13)
H19A	0.48070	0.86620	0.07150	0.1340*	0.337 (13)
H20A	0.36230	0.91730	−0.16370	0.2100*	0.337 (13)
H20B	0.34760	0.95410	−0.03250	0.2100*	0.337 (13)

	U11	U22	U33	U12	U13	U23
O1	0.087 (3)	0.073 (2)	0.105 (3)	0.010 (2)	0.040 (2)	0.020 (2)
N1	0.108 (4)	0.069 (3)	0.091 (4)	−0.020 (3)	0.019 (3)	−0.001 (3)
N2	0.094 (4)	0.098 (4)	0.079 (4)	−0.014 (3)	0.009 (3)	0.004 (3)
N3	0.098 (4)	0.106 (4)	0.071 (3)	−0.013 (3)	0.009 (3)	0.008 (3)
N4	0.083 (3)	0.076 (3)	0.070 (3)	−0.007 (3)	0.011 (3)	0.007 (3)
C1	0.089 (4)	0.087 (5)	0.097 (5)	−0.006 (4)	0.006 (4)	0.011 (4)
C2	0.140 (7)	0.118 (6)	0.089 (5)	−0.032 (5)	0.029 (4)	−0.007 (5)
C3	0.119 (7)	0.089 (6)	0.182 (9)	−0.020 (5)	0.074 (6)	−0.027 (6)
C4	0.082 (6)	0.111 (7)	0.188 (9)	0.005 (5)	0.018 (5)	0.016 (7)
C5	0.097 (5)	0.101 (5)	0.113 (6)	−0.015 (5)	0.005 (4)	0.011 (5)
C6	0.071 (4)	0.065 (4)	0.090 (5)	−0.014 (3)	0.018 (4)	0.016 (4)
C7	0.128 (5)	0.076 (4)	0.095 (5)	−0.019 (4)	0.023 (4)	0.004 (4)
C8	0.092 (5)	0.069 (4)	0.088 (4)	−0.014 (4)	0.025 (4)	−0.014 (4)
C9	0.077 (4)	0.065 (4)	0.084 (4)	−0.008 (3)	0.015 (3)	−0.008 (4)
C10	0.073 (4)	0.068 (4)	0.098 (4)	0.002 (3)	0.015 (3)	0.000 (4)
C11	0.066 (4)	0.077 (4)	0.093 (4)	0.001 (3)	0.030 (3)	−0.005 (4)
C12	0.077 (4)	0.068 (4)	0.082 (4)	0.002 (3)	0.028 (3)	−0.006 (3)
C13	0.079 (4)	0.079 (4)	0.100 (5)	0.003 (3)	0.034 (3)	0.003 (4)
C14	0.078 (4)	0.082 (4)	0.100 (4)	−0.008 (4)	0.039 (3)	0.001 (4)
C15	0.099 (5)	0.078 (4)	0.099 (5)	0.009 (4)	0.032 (3)	0.003 (4)
C16	0.081 (4)	0.074 (4)	0.068 (4)	0.003 (3)	0.017 (3)	0.007 (4)
C17	0.108 (5)	0.084 (4)	0.058 (4)	−0.003 (4)	0.024 (3)	0.002 (4)
C18B	0.080 (6)	0.091 (5)	0.099 (11)	−0.004 (4)	0.016 (7)	0.003 (6)
C19B	0.112 (10)	0.072 (6)	0.137 (14)	0.017 (6)	−0.040 (8)	−0.008 (9)
C20B	0.177 (17)	0.156 (10)	0.18 (2)	0.048 (10)	−0.012 (17)	−0.071 (14)
C20A	0.177 (17)	0.156 (10)	0.18 (2)	0.048 (10)	−0.012 (17)	−0.071 (14)
C18A	0.080 (6)	0.091 (5)	0.099 (11)	−0.004 (4)	0.016 (7)	0.003 (6)
C19A	0.112 (10)	0.072 (6)	0.137 (14)	0.017 (6)	−0.040 (8)	−0.008 (9)

O1—C12	1.373 (7)	C19A—C20A	1.32 (5)
O1—C15	1.441 (7)	C19B—C20B	1.29 (3)
N1—C7	1.472 (7)	C1—H1	0.9300
N1—C8	1.258 (7)	C2—H2	0.9300
N2—N3	1.319 (7)	C3—H3	0.9300
N2—C16	1.347 (8)	C4—H4	0.9300
N3—N4	1.334 (7)	C5—H5	0.9300
N4—C17	1.329 (7)	C7—H7A	0.9700
N4—C18B	1.470 (16)	C7—H7B	0.9700
N4—C18A	1.48 (4)	C8—H8	0.9300
C1—C2	1.365 (10)	C10—H10	0.9300
C1—C6	1.365 (10)	C11—H11	0.9300
C2—C3	1.356 (11)	C13—H13	0.9300
C3—C4	1.359 (13)	C14—H14	0.9300
C4—C5	1.391 (11)	C15—H15A	0.9700
C5—C6	1.377 (10)	C15—H15B	0.9700
C6—C7	1.505 (8)	C17—H17	0.9300
C8—C9	1.477 (8)	C18A—H18B	0.9700
C9—C10	1.378 (8)	C18A—H18A	0.9700
C9—C14	1.378 (8)	C18B—H18D	0.9700
C10—C11	1.382 (8)	C18B—H18C	0.9700
C11—C12	1.375 (8)	C19A—H19A	0.9300
C12—C13	1.384 (7)	C19B—H19B	0.9300
C13—C14	1.381 (8)	C20A—H20B	0.9400
C15—C16	1.490 (8)	C20A—H20A	0.9300
C16—C17	1.342 (8)	C20B—H20D	0.9300
C18A—C19A	1.52 (5)	C20B—H20C	0.9300
C18B—C19B	1.50 (2)
C12—O1—C15	117.3 (4)	C5—C4—H4	120.00
C7—N1—C8	115.9 (5)	C4—C5—H5	120.00
N3—N2—C16	107.8 (4)	C6—C5—H5	120.00
N2—N3—N4	106.8 (4)	N1—C7—H7A	110.00
N3—N4—C17	111.2 (4)	N1—C7—H7B	110.00
N3—N4—C18B	124.0 (9)	C6—C7—H7A	110.00
N3—N4—C18A	110.6 (17)	C6—C7—H7B	110.00
C17—N4—C18B	124.8 (9)	H7A—C7—H7B	108.00
C17—N4—C18A	138.1 (17)	N1—C8—H8	119.00
C2—C1—C6	121.4 (6)	C9—C8—H8	119.00
C1—C2—C3	119.6 (7)	C9—C10—H10	120.00
C2—C3—C4	120.7 (8)	C11—C10—H10	120.00
C3—C4—C5	119.8 (7)	C10—C11—H11	120.00
C4—C5—C6	119.6 (6)	C12—C11—H11	120.00
C1—C6—C5	118.9 (6)	C12—C13—H13	120.00
C1—C6—C7	120.7 (5)	C14—C13—H13	120.00
C5—C6—C7	120.4 (6)	C9—C14—H14	119.00
N1—C7—C6	109.9 (4)	C13—C14—H14	119.00
N1—C8—C9	122.8 (5)	O1—C15—H15A	110.00
C8—C9—C10	123.2 (5)	O1—C15—H15B	110.00
C8—C9—C14	118.3 (5)	C16—C15—H15A	110.00
C10—C9—C14	118.6 (5)	C16—C15—H15B	110.00
C9—C10—C11	120.4 (5)	H15A—C15—H15B	108.00
C10—C11—C12	120.8 (5)	N4—C17—H17	128.00
O1—C12—C11	115.6 (5)	C16—C17—H17	128.00
O1—C12—C13	125.1 (5)	H18A—C18A—H18B	109.00
C11—C12—C13	119.2 (5)	N4—C18A—H18B	111.00
C12—C13—C14	119.5 (5)	C19A—C18A—H18A	110.00
C9—C14—C13	121.5 (5)	N4—C18A—H18A	110.00
O1—C15—C16	109.1 (4)	C19A—C18A—H18B	110.00
N2—C16—C15	120.1 (5)	N4—C18B—H18D	109.00
N2—C16—C17	109.5 (5)	C19B—C18B—H18C	110.00
C15—C16—C17	130.4 (6)	N4—C18B—H18C	110.00
N4—C17—C16	104.8 (5)	H18C—C18B—H18D	108.00
N4—C18A—C19A	106 (3)	C19B—C18B—H18D	110.00
N4—C18B—C19B	110.6 (12)	C20A—C19A—H19A	125.00
C18A—C19A—C20A	111 (3)	C18A—C19A—H19A	124.00
C18B—C19B—C20B	120.9 (19)	C18B—C19B—H19B	120.00
C2—C1—H1	119.00	C20B—C19B—H19B	120.00
C6—C1—H1	119.00	C19A—C20A—H20A	121.00
C1—C2—H2	120.00	C19A—C20A—H20B	120.00
C3—C2—H2	120.00	H20A—C20A—H20B	120.00
C2—C3—H3	120.00	C19B—C20B—H20C	120.00
C4—C3—H3	120.00	C19B—C20B—H20D	120.00
C3—C4—H4	120.00	H20C—C20B—H20D	120.00
C12—O1—C15—C16	−178.3 (4)	C4—C5—C6—C1	−0.1 (10)
C15—O1—C12—C11	179.3 (5)	C1—C6—C7—N1	−70.5 (7)
C15—O1—C12—C13	0.2 (7)	C5—C6—C7—N1	106.7 (6)
C7—N1—C8—C9	−178.6 (5)	N1—C8—C9—C14	−172.7 (5)
C8—N1—C7—C6	112.8 (6)	N1—C8—C9—C10	8.0 (9)
C16—N2—N3—N4	0.8 (6)	C8—C9—C14—C13	−178.9 (5)
N3—N2—C16—C15	179.1 (5)	C8—C9—C10—C11	178.0 (5)
N3—N2—C16—C17	−0.2 (6)	C10—C9—C14—C13	0.3 (8)
N2—N3—N4—C18B	−178.1 (9)	C14—C9—C10—C11	−1.2 (8)
N2—N3—N4—C17	−1.2 (6)	C9—C10—C11—C12	1.5 (8)
C18B—N4—C17—C16	177.9 (9)	C10—C11—C12—C13	−0.8 (8)
N3—N4—C17—C16	1.1 (6)	C10—C11—C12—O1	−180.0 (5)
C17—N4—C18B—C19B	−99.3 (15)	C11—C12—C13—C14	−0.1 (8)
N3—N4—C18B—C19B	77.2 (16)	O1—C12—C13—C14	179.0 (5)
C2—C1—C6—C5	0.6 (10)	C12—C13—C14—C9	0.3 (8)
C2—C1—C6—C7	177.8 (6)	O1—C15—C16—N2	89.9 (6)
C6—C1—C2—C3	−1.3 (11)	O1—C15—C16—C17	−91.1 (7)
C1—C2—C3—C4	1.6 (12)	N2—C16—C17—N4	−0.5 (6)
C2—C3—C4—C5	−1.2 (12)	C15—C16—C17—N4	−179.7 (5)
C3—C4—C5—C6	0.4 (11)	N4—C18B—C19B—C20B	122 (2)
C4—C5—C6—C7	−177.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N3i	0.93	2.54	3.379 (7)	150
C18B—H18D···N1ii	0.97	2.52	3.42 (2)	153
C13—H13···Cg2iii	0.93	2.88	3.638 (6)	139
C18B—H18C···Cg2iv	0.97	2.95	3.706 (18)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯N3i	0.93	2.54	3.379 (7)	150
C18B—H18D⋯N1ii	0.97	2.52	3.42 (2)	153
C13—H13⋯Cg2iii	0.93	2.88	3.638 (6)	139
C18B—H18C⋯Cg2iv	0.97	2.95	3.706 (18)	135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .