(E)-N-(1,3-Benzodioxol-5-yl)-1-(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth­oxy}phen­yl)methanimine

Akkurt, M.; Jarrahpour, A.; Chermahini, M.M.; Shiri, P.; Büyükgüngör, O.

doi:10.1107/S1600536813025749

organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1576

doi:10.1107/S1600536813025749

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(E)-N-(1,3-Benzodioxol-5-yl)-1-(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]methoxy}phenyl)methanimine

Mehmet Akkurt,^a ^* Aliasghar Jarrahpour,^b Mehdi Mohammadi Chermahini,^b Pezhman Shiri ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 16 September 2013; accepted 17 September 2013; online 21 September 2013)

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 methylene C atom displaced by 0.156 (5) Å from the other four atoms (r.m.s. deviation = 0.007Å). In the crystal, the molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds, generating a three-dimensional network.

CCDC reference: 961586

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_r = 362.38
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.103
S = 0.90
3770 reflections
245 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.12 e Å⁻³

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) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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 ).

Supporting information

CCDC reference: 961586

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813025749/hb7140sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813025749/hb7140Isup3.cml

checkCIF report

Comment top

Schiff bases are one of the most important mixed donor systems in coordination chemistry. They result from the condensation of primary amines with carbonyl compounds to give imines containing a C=N bond (Calligaris & Randaccio, 1987). Schiff bases are widely in use for synthetic purposes both by organic and inorganic chemists (Arora et al., 2002). They are used as biological, analytical, polymer and liquid crystalline materials (Tanaka & Shiraishi, 2000). Also, they are used as substrate in the preparation of a large of bioactive and industrial compounds via ring closure, cycloaddition, replacement reaction, cyclization and enantioselective oxidation (Macho et al., 2004). Triazoles are also important class of heterocycles because of their varied biological activities (Singh et al., 2012). Due to their broad range of biological activities and their value as synthetic precursors for pharmaceutical compounds, 1,2,3-triazole derivatives have received increasing attention. Therefore, compound (I), which has the two mentioned features, was synthesized and its X-ray studies is reported here.

As shown in Fig. 1, the 1H-1,2,3-triazole ring (N2–N4/C16/C17) and the 1,3-benzodioxole ring system (O1/O2/C1–C7) of the title compound (I) are almostly planar with maximum deviations of 0.002 (3) Å for N4 and 0.078 (5) Å for C7, respectively. The dihedral angle between the above-mentioned rings 62.91 (15)°. The benzene ring (C9–C14) in the middle of the molecule (I) forms dihedral angles of 65.34 (19) and 3.73 (16)° with the 1H-1,2,3-triazole ring and the 1,3-benzodioxole ring system, respectively. The C1–N1–C8–C9, C12–O3–C15–C16 and N4–C18–C19–C20 torsion angles are 179.5 (3), -176.5 (3) and 126.6 (5)°, respectively.

In the crystal, C—H···O and C—H···N hydrogen bonding interactions (Table 1; Figs. 2 & 3) connect the adjacent molecules, forming three dimensional network. However, C—H···π interactions and π-π stacking interactions are not observed.

Related literature top

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 top

Reaction of 4-((1-allyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde (1.00 mmol) with benzo[d][1,3]dioxol-5-amine (1.00 mmol) in refluxing ethanol gave the title compound. Recrystallization from ethanol gave light brown prisms in 72% yield. Mp: 373–375 K. IR (KBr, cm^-1):1612 (C=N). ¹H-NMR (250 MHz, CDCl₃) δ (p.p.m.): 4.92 (d, 2H, J=7.5 Hz), 5.21 (s, 2H), 5.30 (m, 2H), 5.91 (O—CH₂—O, s, 2H), 5.97 (m, 1H), 6.75 (aromatic H, d, 2H, J=10 Hz), 6.99 (aromatic H, d, 2H, J=10 Hz), 7.19 (aromatic H, s, 1H), 7.81 (aromatic H, d, 2H, J=10 Hz), 7.57 (H triazole, s, 1H), 8.30 (HC═N, s, 1H). ¹³CNMR (62.9 MHz, CDCl₃), δ (p.p.m): 62.8 (CH₂—N), 62.1 (CH₂—O), 101.3 (O—CH₂—O), 101.7–148.2 (aromatic carbons and C=C triazole), 158.0 (C=N).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	Fig. 1. The molecular structure of compound (I) with 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of compound (I) viewed down the a axis. Hydrogen bonds are indicated by broken lines. H atoms not participating in hydrogen bonding have been omitted for clarity.
	Fig. 3. A packing diagram for compound (I), viewed down the c axis, showing the hydrogen-bonding network. H atoms not participating in hydrogen bonding have been omitted for clarity.

(E)-N-(1,3-Benzodioxol-5-yl)-1-(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]methoxy}phenyl)methanimine top

Crystal data top

C₂₀H₁₈N₄O₃	F(000) = 760
M_r = 362.38	D_x = 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

Data collection top

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	R_int = 0.059
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.6°
ω–scans	h = −6→6
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→19
T_min = 0.956, T_max = 0.985	l = −28→26
13771 measured reflections

Refinement top

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	Δρ_max = 0.16 e Å⁻³
245 parameters	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₂₀H₁₈N₄O₃	V = 1813.8 (5) Å³
M_r = 362.38	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.1506 (6) Å	µ = 0.09 mm⁻¹
b = 15.334 (2) Å	T = 296 K
c = 22.965 (5) Å	0.69 × 0.39 × 0.20 mm

Data collection top

STOE IPDS 2 diffractometer	3770 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2125 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.985	R_int = 0.059
13771 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.103	H-atom parameters constrained
S = 0.90	Δρ_max = 0.16 e Å⁻³
3770 reflections	Δρ_min = −0.12 e Å⁻³
245 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, −y, z−1/2; (ii) x−1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, −y, z−1/2; (ii) x−1/2, −y+1/2, −z+1.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-N-(1,3-Benzodioxol-5-yl)-1-(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth­­oxy}phen­yl)methanimine

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organic compounds

(E)-N-(1,3-Benzodioxol-5-yl)-1-(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]methoxy}phenyl)methanimine