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
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
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 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
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Data collection: X-AREA (Stoe & Cie, 2002); cell 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
10.1107/S1600536813025749/hb7140sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813025749/hb7140Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813025749/hb7140Isup3.cml
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).
All H atoms were plocated geometrically with C—H = 0.93 - 0.97 Å, and refined using a riding model with Uiso(H) = 1.2Ueq(C). The
was indeterminate in the present The (120), (130) and (041) reflections were omitted owing to bad agreement.Data collection: X-AREA (Stoe & Cie, 2002); cell
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).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 |
C20H18N4O3 | V = 1813.8 (5) Å3 |
Mr = 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 |
STOE IPDS 2 diffractometer | 3770 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2125 reflections with I > 2σ(I) |
Tmin = 0.956, Tmax = 0.985 | Rint = 0.059 |
13771 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 1 restraint |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.16 e Å−3 |
3770 reflections | Δρmin = −0.12 e Å−3 |
245 parameters |
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 |
Symmetry codes: (i) −x+3/2, −y, z−1/2; (ii) x−1/2, −y+1/2, −z+1. |
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).
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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.