(E)-N-(1,3-Benzodioxol-5-yl)-1-(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth-oxy}phen-yl)methanimine.

In the title compound, C20H18N4O3, the dihedral angles between the central benzene ring and the 1H-1,2,3-triazole ring and the fused benzene ring are 65.34 (19) and 3.64 (18)°, respectively. The dioxole ring adopts a shallow envelope conformation, with the methyl-ene C atom displaced by 0.156 (5) Å from the other four atoms (r.m.s. deviation = 0.007Å). In the crystal, the mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds, generating a three-dimensional network.

Related literature

For background to Schiff base compounds, see: Arora et al. (2002 ▶); Calligaris & Randaccio (1987 ▶); Macho et al. (2004 ▶); Singh et al. (2012 ▶); Tanaka & Shiraishi (2000 ▶).

Experimental

Crystal data

C20H18N4O3

M = 362.38

Orthorhombic,

a = 5.1506 (6) Å

b = 15.334 (2) Å

c = 22.965 (5) Å

V = 1813.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.69 × 0.39 × 0.20 mm

Data collection

STOE IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.956, T max = 0.985

13771 measured reflections

3770 independent reflections

2125 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.103

S = 0.90

3770 reflections

245 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.12 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: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813025749/hb7140sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025749/hb7140Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025749/hb7140Isup3.cml

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

C20H18N4O3	F(000) = 760
Mr = 362.38	Dx = 1.327 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 11139 reflections
a = 5.1506 (6) Å	θ = 1.3–27.2°
b = 15.334 (2) Å	µ = 0.09 mm−1
c = 22.965 (5) Å	T = 296 K
V = 1813.8 (5) Å3	Prism, light brown
Z = 4	0.69 × 0.39 × 0.20 mm

STOE IPDS 2 diffractometer	3770 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2125 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.059
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 1.6°
ω–scans	h = −6→6
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→19
Tmin = 0.956, Tmax = 0.985	l = −28→26
13771 measured reflections

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.103	W = 1/[Σ2(FO2) + (0.0508P)2] WHERE P = (FO2 + 2FC2)/3
S = 0.90	(Δ/σ)max < 0.001
3770 reflections	Δρmax = 0.16 e Å−3
245 parameters	Δρmin = −0.12 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
O1	0.2051 (5)	0.1543 (2)	0.27007 (10)	0.1086 (10)
O2	0.5181 (6)	0.07091 (18)	0.22561 (9)	0.1006 (11)
O3	0.4365 (5)	0.13425 (16)	0.73893 (8)	0.0846 (9)
N1	0.5539 (7)	0.08711 (18)	0.46490 (11)	0.0776 (11)
N2	0.5549 (5)	0.2095 (2)	0.85838 (11)	0.0836 (10)
N3	0.5512 (5)	0.19340 (19)	0.91438 (11)	0.0805 (10)
N4	0.3268 (5)	0.15416 (17)	0.92593 (10)	0.0667 (9)
C1	0.5363 (7)	0.08489 (19)	0.40356 (13)	0.0675 (11)
C2	0.3460 (6)	0.1275 (2)	0.36999 (13)	0.0735 (11)
C3	0.3620 (7)	0.1170 (2)	0.31150 (14)	0.0737 (12)
C4	0.5479 (8)	0.0678 (2)	0.28498 (14)	0.0738 (11)
C5	0.7368 (7)	0.0265 (2)	0.31609 (15)	0.0857 (16)
C6	0.7253 (7)	0.0361 (2)	0.37593 (14)	0.0787 (12)
C7	0.2850 (9)	0.1171 (3)	0.21640 (16)	0.1060 (16)
C8	0.3987 (8)	0.1305 (2)	0.49551 (14)	0.0783 (12)
C9	0.4109 (6)	0.1334 (2)	0.55880 (13)	0.0733 (12)
C10	0.5886 (9)	0.0871 (3)	0.59019 (15)	0.1013 (16)
C11	0.5948 (8)	0.0893 (3)	0.64980 (16)	0.1047 (16)
C12	0.4170 (7)	0.1383 (2)	0.67992 (13)	0.0721 (11)
C13	0.2412 (9)	0.1849 (3)	0.65028 (15)	0.1113 (18)
C14	0.2367 (8)	0.1829 (3)	0.59057 (15)	0.1157 (18)
C15	0.2705 (7)	0.1901 (2)	0.77187 (13)	0.0803 (11)
C16	0.3326 (6)	0.1800 (2)	0.83444 (13)	0.0653 (11)
C17	0.1889 (6)	0.1448 (2)	0.87751 (14)	0.0758 (11)
C18	0.2532 (8)	0.1336 (3)	0.98629 (13)	0.0887 (14)
C19	0.4671 (9)	0.0978 (3)	1.02037 (16)	0.0963 (18)
C20	0.5422 (9)	0.1288 (3)	1.06988 (17)	0.1170 (18)
H2	0.21630	0.16100	0.38710	0.0880*
H5	0.86600	−0.00630	0.29810	0.1030*
H6	0.85030	0.00850	0.39860	0.0940*
H7A	0.15200	0.07780	0.20190	0.1270*
H7B	0.31190	0.16260	0.18770	0.1270*
H8	0.26940	0.16230	0.47680	0.0940*
H10	0.70940	0.05300	0.57050	0.1220*
H11	0.71980	0.05750	0.66990	0.1260*
H13	0.12130	0.21880	0.67030	0.1330*
H14	0.11300	0.21580	0.57090	0.1390*
H15A	0.09040	0.17480	0.76490	0.0970*
H15B	0.29610	0.25020	0.76010	0.0970*
H17	0.02600	0.11920	0.87400	0.0910*
H18A	0.19090	0.18630	1.00500	0.1060*
H18B	0.11160	0.09190	0.98580	0.1060*
H19	0.55480	0.04970	1.00550	0.1160*
H20A	0.45840	0.17680	1.08590	0.1410*
H20B	0.68020	0.10300	1.08950	0.1410*

	U11	U22	U33	U12	U13	U23
O1	0.1206 (19)	0.141 (2)	0.0642 (14)	0.042 (2)	−0.0067 (14)	0.0042 (15)
O2	0.124 (2)	0.120 (2)	0.0578 (15)	0.017 (2)	0.0055 (14)	0.0026 (12)
O3	0.1008 (16)	0.0939 (16)	0.0591 (13)	0.0306 (15)	−0.0030 (12)	−0.0015 (11)
N1	0.092 (2)	0.080 (2)	0.0608 (17)	0.0018 (17)	−0.0005 (16)	0.0038 (14)
N2	0.0768 (17)	0.112 (2)	0.0619 (16)	−0.0184 (17)	0.0002 (13)	0.0072 (15)
N3	0.0732 (17)	0.107 (2)	0.0612 (17)	−0.0200 (17)	0.0011 (14)	0.0006 (14)
N4	0.0618 (14)	0.0779 (16)	0.0605 (15)	−0.0056 (14)	0.0087 (13)	−0.0084 (14)
C1	0.080 (2)	0.0608 (19)	0.0618 (19)	−0.0081 (18)	0.0036 (17)	0.0032 (14)
C2	0.0775 (19)	0.077 (2)	0.066 (2)	0.0063 (19)	0.0018 (16)	−0.0023 (16)
C3	0.084 (2)	0.075 (2)	0.062 (2)	0.004 (2)	−0.0049 (17)	0.0055 (17)
C4	0.093 (2)	0.069 (2)	0.0595 (19)	−0.004 (2)	0.007 (2)	0.0025 (16)
C5	0.097 (3)	0.087 (3)	0.073 (2)	0.010 (2)	0.0141 (19)	0.0074 (19)
C6	0.085 (2)	0.081 (2)	0.070 (2)	0.006 (2)	0.0023 (19)	0.0122 (18)
C7	0.124 (3)	0.129 (3)	0.065 (2)	0.015 (3)	−0.010 (2)	−0.005 (2)
C8	0.098 (2)	0.073 (2)	0.064 (2)	0.005 (2)	−0.0065 (18)	0.0066 (17)
C9	0.094 (2)	0.067 (2)	0.059 (2)	0.003 (2)	−0.0048 (17)	0.0070 (16)
C10	0.120 (3)	0.120 (3)	0.064 (2)	0.050 (3)	0.007 (2)	0.005 (2)
C11	0.121 (3)	0.125 (3)	0.068 (2)	0.057 (3)	−0.001 (2)	0.007 (2)
C12	0.085 (2)	0.075 (2)	0.0562 (19)	0.014 (2)	−0.0066 (16)	0.0015 (16)
C13	0.132 (3)	0.139 (4)	0.063 (2)	0.068 (3)	−0.013 (2)	−0.011 (2)
C14	0.143 (4)	0.133 (3)	0.071 (2)	0.068 (3)	−0.021 (2)	−0.003 (2)
C15	0.078 (2)	0.095 (2)	0.0678 (19)	0.023 (2)	−0.0062 (16)	−0.0114 (17)
C16	0.0604 (18)	0.074 (2)	0.0616 (18)	0.0075 (17)	−0.0012 (15)	−0.0087 (15)
C17	0.0595 (16)	0.094 (2)	0.074 (2)	−0.0092 (17)	0.0001 (18)	−0.0173 (19)
C18	0.088 (2)	0.108 (3)	0.070 (2)	−0.008 (2)	0.0180 (19)	−0.002 (2)
C19	0.129 (4)	0.093 (3)	0.067 (2)	0.012 (3)	0.016 (3)	−0.0023 (19)
C20	0.160 (4)	0.125 (3)	0.066 (2)	0.018 (3)	0.005 (3)	−0.003 (2)

O1—C3	1.373 (4)	C12—C13	1.339 (5)
O1—C7	1.419 (5)	C13—C14	1.372 (5)
O2—C4	1.373 (4)	C15—C16	1.480 (4)
O2—C7	1.410 (6)	C16—C17	1.348 (4)
O3—C12	1.360 (4)	C18—C19	1.459 (6)
O3—C15	1.427 (4)	C19—C20	1.292 (6)
N1—C1	1.412 (4)	C2—H2	0.9300
N1—C8	1.255 (5)	C5—H5	0.9300
N2—N3	1.310 (4)	C6—H6	0.9300
N2—C16	1.348 (4)	C7—H7A	0.9700
N3—N4	1.330 (4)	C7—H7B	0.9700
N4—C17	1.327 (4)	C8—H8	0.9300
N4—C18	1.471 (4)	C10—H10	0.9300
C1—C2	1.408 (4)	C11—H11	0.9300
C1—C6	1.382 (5)	C13—H13	0.9300
C2—C3	1.355 (4)	C14—H14	0.9300
C3—C4	1.363 (5)	C15—H15A	0.9700
C4—C5	1.363 (5)	C15—H15B	0.9700
C5—C6	1.383 (5)	C17—H17	0.9300
C8—C9	1.456 (4)	C18—H18A	0.9700
C9—C10	1.364 (5)	C18—H18B	0.9700
C9—C14	1.383 (5)	C19—H19	0.9300
C10—C11	1.370 (5)	C20—H20A	0.9300
C11—C12	1.372 (5)	C20—H20B	0.9300
C3—O1—C7	105.3 (3)	C18—C19—C20	124.1 (4)
C4—O2—C7	105.2 (3)	C1—C2—H2	122.00
C12—O3—C15	117.2 (3)	C3—C2—H2	122.00
C1—N1—C8	122.0 (3)	C4—C5—H5	122.00
N3—N2—C16	109.0 (3)	C6—C5—H5	122.00
N2—N3—N4	107.1 (2)	C1—C6—H6	118.00
N3—N4—C17	110.3 (2)	C5—C6—H6	119.00
N3—N4—C18	120.6 (3)	O1—C7—H7A	110.00
C17—N4—C18	128.9 (3)	O1—C7—H7B	110.00
N1—C1—C2	125.4 (3)	O2—C7—H7A	110.00
N1—C1—C6	115.2 (3)	O2—C7—H7B	110.00
C2—C1—C6	119.4 (3)	H7A—C7—H7B	108.00
C1—C2—C3	116.4 (3)	N1—C8—H8	118.00
O1—C3—C2	127.0 (3)	C9—C8—H8	118.00
O1—C3—C4	109.5 (3)	C9—C10—H10	119.00
C2—C3—C4	123.5 (3)	C11—C10—H10	119.00
O2—C4—C3	110.3 (3)	C10—C11—H11	120.00
O2—C4—C5	128.1 (3)	C12—C11—H11	120.00
C3—C4—C5	121.6 (3)	C12—C13—H13	120.00
C4—C5—C6	116.2 (3)	C14—C13—H13	120.00
C1—C6—C5	123.0 (3)	C9—C14—H14	119.00
O1—C7—O2	108.6 (3)	C13—C14—H14	119.00
N1—C8—C9	123.2 (3)	O3—C15—H15A	110.00
C8—C9—C10	122.7 (3)	O3—C15—H15B	110.00
C8—C9—C14	121.0 (3)	C16—C15—H15A	110.00
C10—C9—C14	116.2 (3)	C16—C15—H15B	110.00
C9—C10—C11	122.1 (4)	H15A—C15—H15B	108.00
C10—C11—C12	120.1 (4)	N4—C17—H17	127.00
O3—C12—C11	115.3 (3)	C16—C17—H17	127.00
O3—C12—C13	125.5 (3)	N4—C18—H18A	109.00
C11—C12—C13	119.2 (3)	N4—C18—H18B	109.00
C12—C13—C14	120.5 (4)	C19—C18—H18A	109.00
C9—C14—C13	121.9 (4)	C19—C18—H18B	109.00
O3—C15—C16	108.8 (3)	H18A—C18—H18B	108.00
N2—C16—C15	123.0 (3)	C18—C19—H19	118.00
N2—C16—C17	107.5 (3)	C20—C19—H19	118.00
C15—C16—C17	129.5 (3)	C19—C20—H20A	120.00
N4—C17—C16	106.1 (3)	C19—C20—H20B	120.00
N4—C18—C19	113.1 (3)	H20A—C20—H20B	120.00
C3—O1—C7—O2	−10.7 (4)	C1—C2—C3—O1	−177.6 (3)
C7—O1—C3—C2	−174.9 (4)	O1—C3—C4—C5	177.1 (3)
C7—O1—C3—C4	6.8 (4)	O1—C3—C4—O2	−0.3 (4)
C7—O2—C4—C5	176.5 (4)	C2—C3—C4—C5	−1.4 (5)
C4—O2—C7—O1	10.5 (4)	C2—C3—C4—O2	−178.7 (3)
C7—O2—C4—C3	−6.4 (4)	O2—C4—C5—C6	178.1 (3)
C12—O3—C15—C16	−176.5 (3)	C3—C4—C5—C6	1.2 (5)
C15—O3—C12—C13	−5.8 (5)	C4—C5—C6—C1	−0.5 (5)
C15—O3—C12—C11	174.6 (3)	N1—C8—C9—C14	179.4 (4)
C1—N1—C8—C9	179.5 (3)	N1—C8—C9—C10	−1.8 (6)
C8—N1—C1—C2	−1.7 (5)	C8—C9—C14—C13	178.5 (4)
C8—N1—C1—C6	178.3 (3)	C8—C9—C10—C11	−178.8 (4)
C16—N2—N3—N4	−0.3 (4)	C10—C9—C14—C13	−0.4 (6)
N3—N2—C16—C17	0.1 (4)	C14—C9—C10—C11	0.0 (6)
N3—N2—C16—C15	178.2 (3)	C9—C10—C11—C12	0.8 (7)
N2—N3—N4—C17	0.4 (3)	C10—C11—C12—C13	−1.2 (6)
N2—N3—N4—C18	−175.1 (3)	C10—C11—C12—O3	178.5 (4)
C17—N4—C18—C19	142.4 (4)	C11—C12—C13—C14	0.8 (6)
C18—N4—C17—C16	174.6 (3)	O3—C12—C13—C14	−178.8 (4)
N3—N4—C17—C16	−0.4 (4)	C12—C13—C14—C9	0.0 (7)
N3—N4—C18—C19	−43.1 (5)	O3—C15—C16—N2	70.4 (4)
C6—C1—C2—C3	0.2 (5)	O3—C15—C16—C17	−111.9 (4)
N1—C1—C6—C5	179.7 (3)	N2—C16—C17—N4	0.2 (4)
C2—C1—C6—C5	−0.3 (5)	C15—C16—C17—N4	−177.8 (3)
N1—C1—C2—C3	−179.8 (3)	N4—C18—C19—C20	126.6 (5)
C1—C2—C3—C4	0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3i	0.93	2.59	3.471 (4)	157
C7—H7B···N2ii	0.97	2.59	3.380 (5)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3i	0.93	2.59	3.471 (4)	157
C7—H7B⋯N2ii	0.97	2.59	3.380 (5)	138

Symmetry codes: (i) ; (ii) .