Crystal structure of {(E)-4-[(1-allyl-1H-1,2,3-triazol-4-yl)meth­oxy]benzyl­idene}[2-(morpholin-4-yl)eth­yl]amine

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

doi:10.1107/S1600536814016754

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o933-o934

doi:10.1107/S1600536814016754

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Crystal structure of {(E)-4-[(1-allyl-1H-1,2,3-triazol-4-yl)methoxy]benzylidene}[2-(morpholin-4-yl)ethyl]amine

Sevim Türktekin Çelikesir,^a 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

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 July 2014; accepted 19 July 2014; online 1 August 2014)

In the title compound, C₁₉H₂₅N₅O₂, the morpholine ring has a chair conformation. The plane of the central benzene ring makes dihedral angles of 88.75 (12) and 60.02 (7)°, respectively, with the mean plane formed by the four planar C atoms of the morpholine ring and with the plane of the triazole ring. In the crystal, molecules are linked via C—H⋯π interactions, forming slabs lying parallel to (10-1). The C atoms of the bridging ethylene group, between the morpholine and benzene rings, and the terminal ethene group of the prop-1-ene substituent attached to the triazole ring, are disordered over two sets of sites, with an occupancy ratio of 0.634 (13):0.366 (13).

Keywords: crystal structure; Schiff base; morpholine; 1,2,3-triazole; disorder.

CCDC reference: 1014976

1. Related literature

For information on Schiff bases, see: Vladimirova et al. (2001 ). For 1,2,3-triazole derivatives and the `click' chemistry concept, see: Kolb et al. (2001 ); Wang et al. (2005 ). For the biological activity of 1,2,3-triazole derivatives, including their potential applications as antitumor, antibacterial, antifungal and antiviral agents, see: Yu et al. (2006 ). For the biological utility of molecules containing the morpholine moiety, see: Nelson et al. (2004 ).

2. Experimental

2.1. Crystal data

C₁₉H₂₅N₅O₂
M_r = 355.44
Monoclinic, P 2₁ /c
a = 22.3034 (10) Å
b = 5.2531 (3) Å
c = 16.5878 (8) Å
β = 93.051 (4)°
V = 1940.71 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.61 × 0.43 × 0.10 mm

2.2. Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.961, T_max = 0.993
25155 measured reflections
3610 independent reflections
1769 reflections with I > 2σ(I)
R_int = 0.191

2.3. Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.130
S = 0.93
3610 reflections
272 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the 1,2,3-triazole ring N3–N5/C15/C16.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6A—H6A1⋯Cgⁱ	0.97	2.90	3.617 (8)	132
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: 1014976

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814016754/su2753sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016754/su2753Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016754/su2753Isup3.cml

checkCIF report

Synthesis and crystallization top

Reaction of 4-((1-allyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde (1.0 mmol) with 2-morpholinoethanamine (1.0 mmol) in refluxing ethanol gave the title compound. Recrystallization from ethanol gave light brown crystals in 75% yield. m.p. 385 - 387 K. IR (KBr, cm^-1): 1635 (C=N). ¹H-NMR (250 MHz, CDCl₃), δ (ppm): 2.48 (CH₂—N morpholine, t, 4H, J=5 Hz), 2.62 (morpholine-CH₂—CH₂, t, 2H, J=7.5 Hz), 3.65 (CH₂—O morpholine and morpholine-CH₂—CH₂, t, 6H, J=5 Hz), 4.92 (d, 2H, J=7.5 Hz), 5.17 (s, 2H), 5.29 (m, 2H), 5.98 (m, 1H), 6.92 (aromatic H, d, 2H, J=10 Hz), 7.56 (aromatic H, d, 2H, J= Hz 5), 7.6 (H triazole, s, 1H), 8.15 (HC═N, s, 1H). ¹³CNMR (62.9 MHz, CDCl₃), δ (p.p.m): 53.9 (CH₂—N morpholine), 58.8, 59.3 (N—CH₂—CH₂, and CH₂—N), 61.9 (CH₂—O), 66.9 (CH₂—O morpholine), 114.7-143.9 (aromatic carbons and C=C triazole), 161.1 (C=N).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were included in calculated positions and treated as riding atoms: C—H = 0.93 - 0.97 Å with U_iso(H) = 1.2U_eq(C). Reflections (1 2 0), (1 3 0) and (0 4 1) were omitted owing to bad agreement. Atoms C5A/C5B, C6A/C6B, C18A/C18B and C19A/C19B are disordered over two sites with an occupancy ratio of 0.634 (13):0.366 (13). Owing to the poor quality of the crystal the value of R_int is high (0.191).

Related literature top

For information on Schiff bases, see: Vladimirova et al. (2001). For 1,2,3-triazole derivatives and the `click' chemistry concept, see: Kolb et al. (2001); Wang et al. (2005). For the biological activity of 1,2,3-triazole derivatives, including their potential applications as antitumor, antibacterial, antifungal and antiviral agents, see: Yu et al. (2006). For the biological utility of molecules containing the morpholine moiety, see: Nelson et al. (2004).

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 the title molecule, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level. For clarity only the major disordered components are shown.
	Fig. 2. Crystal packing diagram of the title compound viewed along the b axis. For clarity only the major disordered components are shown.

{(E)-4-[(1-Allyl-1H-1,2,3-triazol-4-yl)methoxy]benzylidene}[2-(morpholin-4-yl)ethyl]amine top

Crystal data top

C₁₉H₂₅N₅O₂	F(000) = 760
M_r = 355.44	D_x = 1.217 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15061 reflections
a = 22.3034 (10) Å	θ = 1.5–27.1°
b = 5.2531 (3) Å	µ = 0.08 mm⁻¹
c = 16.5878 (8) Å	T = 296 K
β = 93.051 (4)°	Block, light brown
V = 1940.71 (17) Å³	0.61 × 0.43 × 0.10 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	3610 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1769 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.191
Detector resolution: 6.67 pixels mm^-1	θ_max = 25.5°, θ_min = 1.8°
ω scans	h = −26→26
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −6→6
T_min = 0.961, T_max = 0.993	l = −20→20
25155 measured reflections

Refinement top

Refinement on F²	7 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0624P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max = 0.001
3610 reflections	Δρ_max = 0.16 e Å⁻³
272 parameters	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₉H₂₅N₅O₂	V = 1940.71 (17) Å³
M_r = 355.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.3034 (10) Å	µ = 0.08 mm⁻¹
b = 5.2531 (3) Å	T = 296 K
c = 16.5878 (8) Å	0.61 × 0.43 × 0.10 mm
β = 93.051 (4)°

Data collection top

Stoe IPDS 2 diffractometer	3610 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1769 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.993	R_int = 0.191
25155 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	7 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 0.93	Δρ_max = 0.16 e Å⁻³
3610 reflections	Δρ_min = −0.14 e Å⁻³
272 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	Occ. (<1)
O1	0.00977 (10)	0.1772 (6)	0.1080 (2)	0.1613 (15)
O2	0.52892 (6)	0.7614 (3)	0.42272 (9)	0.0777 (6)
N1	0.12323 (13)	0.3855 (6)	0.15681 (19)	0.1249 (11)
N2	0.27681 (10)	0.5151 (6)	0.24066 (15)	0.1151 (10)
N3	0.65963 (9)	0.6517 (4)	0.44128 (13)	0.0839 (8)
N4	0.70715 (9)	0.6485 (4)	0.49113 (14)	0.0923 (9)
N5	0.70797 (8)	0.8676 (4)	0.53186 (12)	0.0807 (8)
C1	0.0707 (2)	0.4126 (9)	0.2028 (3)	0.172 (2)
C2	0.01503 (16)	0.4008 (10)	0.1505 (3)	0.179 (3)
C3	0.05926 (16)	0.1478 (10)	0.0616 (3)	0.180 (2)
C4	0.11659 (13)	0.1510 (8)	0.1120 (2)	0.1436 (18)
C5A	0.1714 (3)	0.4194 (16)	0.2175 (5)	0.096 (2)	0.634 (13)
C6A	0.2293 (3)	0.482 (2)	0.1740 (5)	0.096 (3)	0.634 (13)
C7	0.31518 (10)	0.6820 (5)	0.23080 (15)	0.0809 (10)
C8	0.37040 (9)	0.7061 (4)	0.28150 (13)	0.0658 (8)
C9	0.38592 (9)	0.5339 (4)	0.34293 (14)	0.0711 (8)
C10	0.43840 (9)	0.5580 (4)	0.38852 (14)	0.0695 (8)
C11	0.47744 (9)	0.7556 (4)	0.37429 (13)	0.0646 (8)
C12	0.46337 (10)	0.9286 (4)	0.31340 (14)	0.0774 (9)
C13	0.40997 (11)	0.9006 (4)	0.26846 (15)	0.0805 (9)
C14	0.57484 (10)	0.9369 (4)	0.40298 (15)	0.0775 (9)
C15	0.63014 (9)	0.8731 (4)	0.45100 (13)	0.0644 (8)
C16	0.66101 (11)	1.0086 (5)	0.50812 (15)	0.0795 (9)
C17	0.75478 (13)	0.9218 (7)	0.59454 (18)	0.1190 (14)
C18A	0.7974 (4)	1.113 (2)	0.5714 (7)	0.114 (3)	0.634 (13)
C19A	0.8541 (6)	1.080 (3)	0.5825 (11)	0.151 (5)	0.634 (13)
C5B	0.1961 (5)	0.338 (2)	0.1835 (7)	0.083 (4)	0.366 (13)
C6B	0.2144 (7)	0.590 (3)	0.2047 (9)	0.104 (5)	0.366 (13)
C18B	0.8105 (6)	0.998 (4)	0.5629 (12)	0.109 (6)	0.366 (13)
C19B	0.8417 (14)	1.199 (3)	0.579 (2)	0.153 (10)	0.366 (13)
H1A	0.07240	0.57420	0.23110	0.2060*
H1B	0.07020	0.27810	0.24280	0.2060*
H5A1	0.17700	0.26510	0.24920	0.1160*	0.634 (13)
H3A	0.05980	0.28410	0.02220	0.2160*
H3B	0.05590	−0.01220	0.03260	0.2160*
H6A2	0.22430	0.63690	0.14260	0.1150*	0.634 (13)
H5A2	0.16200	0.55730	0.25360	0.1160*	0.634 (13)
H2A	−0.01930	0.41900	0.18370	0.2150*
H2B	0.01450	0.54230	0.11290	0.2150*
H6A1	0.23960	0.34400	0.13840	0.1150*	0.634 (13)
H10	0.44790	0.44120	0.42930	0.0830*
H12	0.48940	1.06130	0.30290	0.0930*
H13	0.40040	1.01780	0.22780	0.0970*
H14A	0.56250	1.10930	0.41490	0.0930*
H14B	0.58190	0.92630	0.34590	0.0930*
H16	0.65130	1.16920	0.52710	0.0950*
H17A	0.73600	0.97870	0.64280	0.1430*
H17B	0.77630	0.76560	0.60780	0.1430*
H18A	0.78320	1.26370	0.54790	0.1370*	0.634 (13)
H19A	0.86880	0.93050	0.60600	0.1820*	0.634 (13)
H19B	0.88050	1.20590	0.56710	0.1820*	0.634 (13)
H4A	0.11720	0.00870	0.14930	0.1720*
H4B	0.15010	0.13150	0.07760	0.1720*
H7	0.30840	0.79780	0.18890	0.0970*
H9	0.36010	0.40000	0.35310	0.0850*
H5B1	0.20110	0.22290	0.22900	0.0990*	0.366 (13)
H5B2	0.21790	0.27290	0.13880	0.0990*	0.366 (13)
H6B1	0.18950	0.66640	0.24420	0.1250*	0.366 (13)
H6B2	0.21640	0.70040	0.15800	0.1250*	0.366 (13)
H18B	0.82620	0.88730	0.52550	0.1310*	0.366 (13)
H19C	0.82840	1.31630	0.61640	0.1840*	0.366 (13)
H19D	0.87750	1.22610	0.55460	0.1840*	0.366 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0905 (16)	0.195 (3)	0.196 (3)	−0.0408 (17)	−0.0134 (17)	−0.031 (2)
O2	0.0721 (9)	0.0850 (10)	0.0749 (11)	−0.0148 (8)	−0.0063 (8)	0.0196 (8)
N1	0.1009 (18)	0.141 (2)	0.127 (2)	−0.0382 (17)	−0.0480 (18)	0.0348 (19)
N2	0.0763 (14)	0.164 (2)	0.1018 (18)	−0.0213 (15)	−0.0260 (13)	0.0395 (17)
N3	0.0847 (13)	0.0753 (13)	0.0906 (16)	0.0021 (11)	−0.0044 (12)	−0.0121 (11)
N4	0.0861 (14)	0.0884 (15)	0.1015 (17)	0.0078 (12)	−0.0030 (13)	−0.0022 (13)
N5	0.0753 (13)	0.0914 (14)	0.0747 (14)	−0.0147 (12)	−0.0029 (11)	0.0018 (12)
C1	0.147 (3)	0.194 (4)	0.171 (4)	−0.033 (3)	−0.022 (3)	−0.030 (3)
C2	0.101 (3)	0.206 (5)	0.227 (5)	−0.006 (3)	−0.021 (3)	−0.035 (4)
C3	0.090 (2)	0.266 (5)	0.180 (4)	−0.035 (3)	−0.021 (3)	−0.065 (4)
C4	0.090 (2)	0.183 (4)	0.156 (3)	−0.008 (2)	−0.011 (2)	−0.001 (3)
C5A	0.066 (3)	0.141 (5)	0.082 (4)	−0.004 (3)	0.001 (3)	0.001 (3)
C6A	0.059 (3)	0.151 (7)	0.077 (5)	−0.011 (4)	0.000 (3)	−0.001 (4)
C7	0.0742 (15)	0.1012 (19)	0.0670 (16)	0.0125 (14)	0.0008 (13)	0.0074 (14)
C8	0.0673 (13)	0.0702 (14)	0.0597 (15)	0.0124 (11)	0.0007 (11)	−0.0038 (11)
C9	0.0664 (14)	0.0790 (14)	0.0680 (16)	−0.0028 (11)	0.0048 (12)	0.0050 (13)
C10	0.0686 (13)	0.0735 (14)	0.0664 (15)	−0.0002 (11)	0.0041 (12)	0.0155 (11)
C11	0.0681 (13)	0.0658 (13)	0.0594 (14)	0.0053 (11)	−0.0024 (11)	0.0016 (11)
C12	0.0843 (16)	0.0622 (14)	0.0844 (18)	−0.0044 (11)	−0.0085 (14)	0.0129 (12)
C13	0.0953 (17)	0.0662 (14)	0.0785 (18)	0.0044 (13)	−0.0104 (14)	0.0156 (12)
C14	0.0825 (15)	0.0649 (13)	0.0845 (18)	−0.0127 (11)	0.0003 (13)	0.0070 (12)
C15	0.0676 (13)	0.0558 (12)	0.0697 (15)	−0.0082 (11)	0.0032 (12)	0.0023 (11)
C16	0.0864 (16)	0.0665 (13)	0.0849 (18)	−0.0048 (13)	−0.0009 (14)	−0.0124 (13)
C17	0.0904 (19)	0.175 (3)	0.089 (2)	−0.029 (2)	−0.0193 (17)	0.002 (2)
C18A	0.094 (5)	0.092 (5)	0.152 (6)	−0.016 (5)	−0.042 (5)	−0.009 (5)
C19A	0.093 (6)	0.206 (13)	0.153 (7)	−0.026 (9)	−0.007 (5)	0.020 (11)
C5B	0.071 (7)	0.119 (7)	0.057 (6)	0.029 (5)	0.000 (5)	0.002 (5)
C6B	0.114 (10)	0.128 (10)	0.068 (8)	0.010 (8)	−0.008 (6)	0.006 (6)
C18B	0.066 (9)	0.125 (12)	0.134 (9)	0.009 (7)	−0.011 (6)	−0.027 (10)
C19B	0.116 (17)	0.127 (13)	0.217 (19)	−0.036 (11)	0.016 (14)	−0.018 (14)

Geometric parameters (Å, º) top

O1—C2	1.372 (6)	C1—H1A	0.9700
O1—C3	1.388 (5)	C1—H1B	0.9700
O2—C11	1.366 (2)	C2—H2A	0.9700
O2—C14	1.429 (3)	C2—H2B	0.9700
N1—C1	1.439 (5)	C3—H3A	0.9700
N1—C4	1.442 (5)	C3—H3B	0.9700
N1—C5A	1.444 (8)	C4—H4A	0.9700
N1—C5B	1.680 (12)	C4—H4B	0.9700
N2—C6A	1.500 (8)	C5A—H5A1	0.9700
N2—C7	1.242 (4)	C5A—H5A2	0.9700
N2—C6B	1.536 (16)	C5B—H5B1	0.9700
N3—N4	1.309 (3)	C5B—H5B2	0.9700
N3—C15	1.350 (3)	C6A—H6A2	0.9700
N4—N5	1.334 (3)	C6A—H6A1	0.9700
N5—C16	1.325 (3)	C6B—H6B2	0.9700
N5—C17	1.462 (4)	C6B—H6B1	0.9700
C1—C2	1.478 (6)	C7—H7	0.9300
C3—C4	1.490 (5)	C9—H9	0.9300
C5A—C6A	1.548 (10)	C10—H10	0.9300
C5B—C6B	1.424 (19)	C12—H12	0.9300
C7—C8	1.459 (3)	C13—H13	0.9300
C8—C9	1.392 (3)	C14—H14A	0.9700
C8—C13	1.375 (3)	C14—H14B	0.9700
C9—C10	1.365 (3)	C16—H16	0.9300
C10—C11	1.383 (3)	C17—H17A	0.9700
C11—C12	1.382 (3)	C17—H17B	0.9700
C12—C13	1.379 (3)	C18A—H18A	0.9300
C14—C15	1.471 (3)	C18B—H18B	0.9300
C15—C16	1.345 (3)	C19A—H19B	0.9300
C17—C18B	1.432 (15)	C19A—H19A	0.9300
C17—C18A	1.449 (10)	C19B—H19C	0.9300
C18A—C19A	1.280 (16)	C19B—H19D	0.9300
C18B—C19B	1.29 (3)

C2—O1—C3	109.4 (3)	N1—C4—H4B	109.00
C11—O2—C14	118.02 (17)	C3—C4—H4A	109.00
C1—N1—C4	107.1 (3)	C3—C4—H4B	110.00
C1—N1—C5A	102.4 (4)	H4A—C4—H4B	108.00
C1—N1—C5B	132.7 (5)	N1—C5A—H5A1	110.00
C4—N1—C5A	121.1 (4)	N1—C5A—H5A2	110.00
C4—N1—C5B	94.6 (4)	C6A—C5A—H5A1	110.00
C6A—N2—C7	116.7 (4)	C6A—C5A—H5A2	110.00
C6B—N2—C7	112.6 (6)	H5A1—C5A—H5A2	108.00
N4—N3—C15	108.6 (2)	H5B1—C5B—H5B2	109.00
N3—N4—N5	107.31 (19)	N1—C5B—H5B2	112.00
N4—N5—C16	110.0 (2)	C6B—C5B—H5B1	112.00
N4—N5—C17	121.2 (2)	N1—C5B—H5B1	112.00
C16—N5—C17	128.7 (2)	C6B—C5B—H5B2	112.00
N1—C1—C2	111.5 (4)	N2—C6A—H6A2	111.00
O1—C2—C1	112.6 (4)	C5A—C6A—H6A1	111.00
O1—C3—C4	111.8 (4)	N2—C6A—H6A1	111.00
N1—C4—C3	111.1 (3)	C5A—C6A—H6A2	111.00
N1—C5A—C6A	108.0 (6)	H6A1—C6A—H6A2	109.00
N1—C5B—C6B	100.8 (9)	N2—C6B—H6B1	113.00
N2—C6A—C5A	104.8 (6)	C5B—C6B—H6B2	113.00
N2—C6B—C5B	95.7 (10)	N2—C6B—H6B2	113.00
N2—C7—C8	123.5 (2)	C5B—C6B—H6B1	113.00
C9—C8—C13	117.5 (2)	H6B1—C6B—H6B2	110.00
C7—C8—C9	122.3 (2)	N2—C7—H7	118.00
C7—C8—C13	120.2 (2)	C8—C7—H7	118.00
C8—C9—C10	121.17 (19)	C10—C9—H9	119.00
C9—C10—C11	120.3 (2)	C8—C9—H9	119.00
O2—C11—C12	124.47 (19)	C9—C10—H10	120.00
C10—C11—C12	119.8 (2)	C11—C10—H10	120.00
O2—C11—C10	115.68 (19)	C11—C12—H12	121.00
C11—C12—C13	118.7 (2)	C13—C12—H12	121.00
C8—C13—C12	122.5 (2)	C8—C13—H13	119.00
O2—C14—C15	108.63 (18)	C12—C13—H13	119.00
C14—C15—C16	130.1 (2)	O2—C14—H14A	110.00
N3—C15—C14	122.10 (19)	O2—C14—H14B	110.00
N3—C15—C16	107.8 (2)	C15—C14—H14A	110.00
N5—C16—C15	106.3 (2)	C15—C14—H14B	110.00
N5—C17—C18A	113.6 (5)	H14A—C14—H14B	108.00
N5—C17—C18B	113.3 (8)	C15—C16—H16	127.00
C17—C18A—C19A	121.7 (11)	N5—C16—H16	127.00
C17—C18B—C19B	129 (2)	N5—C17—H17A	109.00
N1—C1—H1A	109.00	C18A—C17—H17B	109.00
N1—C1—H1B	109.00	N5—C17—H17B	109.00
C2—C1—H1A	109.00	C18A—C17—H17A	109.00
C2—C1—H1B	109.00	C18B—C17—H17B	84.00
H1A—C1—H1B	108.00	H17A—C17—H17B	108.00
O1—C2—H2A	109.00	C18B—C17—H17A	130.00
O1—C2—H2B	109.00	C19A—C18A—H18A	119.00
C1—C2—H2A	109.00	C17—C18A—H18A	119.00
C1—C2—H2B	109.00	C19B—C18B—H18B	116.00
H2A—C2—H2B	108.00	C17—C18B—H18B	116.00
O1—C3—H3A	109.00	C18A—C19A—H19B	120.00
O1—C3—H3B	109.00	H19A—C19A—H19B	120.00
C4—C3—H3A	109.00	C18A—C19A—H19A	120.00
C4—C3—H3B	109.00	C18B—C19B—H19C	120.00
H3A—C3—H3B	108.00	C18B—C19B—H19D	120.00
N1—C4—H4A	109.00	H19C—C19B—H19D	120.00

C2—O1—C3—C4	57.7 (5)	N4—N5—C16—C15	0.0 (3)
C3—O1—C2—C1	−57.7 (5)	N1—C1—C2—O1	58.5 (5)
C14—O2—C11—C12	−8.4 (3)	O1—C3—C4—N1	−58.5 (5)
C11—O2—C14—C15	−167.78 (18)	N1—C5A—C6A—N2	179.8 (6)
C14—O2—C11—C10	170.68 (19)	N2—C7—C8—C13	−178.0 (3)
C1—N1—C4—C3	55.4 (4)	N2—C7—C8—C9	3.4 (4)
C4—N1—C5A—C6A	79.1 (7)	C7—C8—C13—C12	−178.5 (2)
C4—N1—C1—C2	−55.3 (5)	C7—C8—C9—C10	178.8 (2)
C5A—N1—C1—C2	176.3 (5)	C9—C8—C13—C12	0.1 (3)
C1—N1—C5A—C6A	−161.9 (6)	C13—C8—C9—C10	0.1 (3)
C5A—N1—C4—C3	172.1 (5)	C8—C9—C10—C11	−0.1 (3)
C6A—N2—C7—C8	−167.7 (4)	C9—C10—C11—C12	−0.3 (3)
C7—N2—C6A—C5A	−143.5 (5)	C9—C10—C11—O2	−179.44 (19)
C15—N3—N4—N5	−0.4 (3)	C10—C11—C12—C13	0.6 (3)
N4—N3—C15—C14	179.4 (2)	O2—C11—C12—C13	179.6 (2)
N4—N3—C15—C16	0.4 (3)	C11—C12—C13—C8	−0.5 (3)
N3—N4—N5—C16	0.3 (3)	O2—C14—C15—N3	65.1 (3)
N3—N4—N5—C17	178.3 (2)	O2—C14—C15—C16	−116.2 (3)
C17—N5—C16—C15	−177.8 (2)	N3—C15—C16—N5	−0.3 (3)
N4—N5—C17—C18A	108.4 (5)	C14—C15—C16—N5	−179.1 (2)
C16—N5—C17—C18A	−74.0 (5)	N5—C17—C18A—C19A	−132.7 (12)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the 1,2,3-triazole ring N3–N5/C15/C16.

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6A1···Cgⁱ	0.97	2.90	3.617 (8)	132

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the 1,2,3-triazole ring N3–N5/C15/C16.

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6A1···Cgⁱ	0.97	2.90	3.617 (8)	132

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

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). AJ, MMC and PS thank the Shiraz University Council for financial support.

References

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o933-o934

doi:10.1107/S1600536814016754

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

Crystal structure of {(E)-4-[(1-allyl-1H-1,2,3-triazol-4-yl)meth­­oxy]benzyl­­idene}[2-(morpholin-4-yl)eth­yl]amine

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of {(E)-4-[(1-allyl-1H-1,2,3-triazol-4-yl)methoxy]benzylidene}[2-(morpholin-4-yl)ethyl]amine