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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 70| Part 9| September 2014| Pages o933-o934

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

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).

1. Related literature

For information on Schiff bases, see: Vladimirova et al. (2001[Vladimirova, M. P., Simova, S. D., Stanoeva, E. R. & Mitewa, M. I. (2001). Dyes Pigm. 50, 157-162.]). For 1,2,3-triazole derivatives and the `click' chemistry concept, see: Kolb et al. (2001[Kolb, H. C., Finn, M. G. & Sharpless, K. B. (2001). Angew. Chem. Int. Ed. 40, 2004-2021.]); Wang et al. (2005[Wang, Q., Chittaboina, S. & Barnhill, H. N. (2005). Lett. Org. Chem. 2, 293-301.]). 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[Yu, H. X., Ma, J. F., Xu, G. H., Li, S. L., Yang, J., Liu, Y. Y. & Cheng, Y. X. (2006). J. Organomet. Chem. 691, 3531-3539.]). For the biological utility of mol­ecules containing the morpholine moiety, see: Nelson et al. (2004[Nelson, T. D., Rosen, J. D., Brands, K. M. J., Craig, B., Huffman, M. A. & McNamara, J. M. (2004). Tetrahedron Lett. 45, 8917-8920.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C19H25N5O2

  • Mr = 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[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.961, Tmax = 0.993

  • 25155 measured reflections

  • 3610 independent reflections

  • 1769 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.16 e Å−3

  • Δρmin = −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 DA 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[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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 (HCN, 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 Uiso(H) = 1.2Ueq(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 Rint 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
[Figure 1] 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.
[Figure 2] 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
C19H25N5O2F(000) = 760
Mr = 355.44Dx = 1.217 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15061 reflections
a = 22.3034 (10) Åθ = 1.5–27.1°
b = 5.2531 (3) ŵ = 0.08 mm1
c = 16.5878 (8) ÅT = 296 K
β = 93.051 (4)°Block, light brown
V = 1940.71 (17) Å30.61 × 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 focus1769 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.191
Detector resolution: 6.67 pixels mm-1θmax = 25.5°, θmin = 1.8°
ω scansh = 2626
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 66
Tmin = 0.961, Tmax = 0.993l = 2020
25155 measured reflections
Refinement top
Refinement on F27 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0624P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.001
3610 reflectionsΔρmax = 0.16 e Å3
272 parametersΔρmin = 0.14 e Å3
Crystal data top
C19H25N5O2V = 1940.71 (17) Å3
Mr = 355.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 22.3034 (10) ŵ = 0.08 mm1
b = 5.2531 (3) ÅT = 296 K
c = 16.5878 (8) Å0.61 × 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)
Tmin = 0.961, Tmax = 0.993Rint = 0.191
25155 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0547 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 0.93Δρmax = 0.16 e Å3
3610 reflectionsΔρmin = 0.14 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.00977 (10)0.1772 (6)0.1080 (2)0.1613 (15)
O20.52892 (6)0.7614 (3)0.42272 (9)0.0777 (6)
N10.12323 (13)0.3855 (6)0.15681 (19)0.1249 (11)
N20.27681 (10)0.5151 (6)0.24066 (15)0.1151 (10)
N30.65963 (9)0.6517 (4)0.44128 (13)0.0839 (8)
N40.70715 (9)0.6485 (4)0.49113 (14)0.0923 (9)
N50.70797 (8)0.8676 (4)0.53186 (12)0.0807 (8)
C10.0707 (2)0.4126 (9)0.2028 (3)0.172 (2)
C20.01503 (16)0.4008 (10)0.1505 (3)0.179 (3)
C30.05926 (16)0.1478 (10)0.0616 (3)0.180 (2)
C40.11659 (13)0.1510 (8)0.1120 (2)0.1436 (18)
C5A0.1714 (3)0.4194 (16)0.2175 (5)0.096 (2)0.634 (13)
C6A0.2293 (3)0.482 (2)0.1740 (5)0.096 (3)0.634 (13)
C70.31518 (10)0.6820 (5)0.23080 (15)0.0809 (10)
C80.37040 (9)0.7061 (4)0.28150 (13)0.0658 (8)
C90.38592 (9)0.5339 (4)0.34293 (14)0.0711 (8)
C100.43840 (9)0.5580 (4)0.38852 (14)0.0695 (8)
C110.47744 (9)0.7556 (4)0.37429 (13)0.0646 (8)
C120.46337 (10)0.9286 (4)0.31340 (14)0.0774 (9)
C130.40997 (11)0.9006 (4)0.26846 (15)0.0805 (9)
C140.57484 (10)0.9369 (4)0.40298 (15)0.0775 (9)
C150.63014 (9)0.8731 (4)0.45100 (13)0.0644 (8)
C160.66101 (11)1.0086 (5)0.50812 (15)0.0795 (9)
C170.75478 (13)0.9218 (7)0.59454 (18)0.1190 (14)
C18A0.7974 (4)1.113 (2)0.5714 (7)0.114 (3)0.634 (13)
C19A0.8541 (6)1.080 (3)0.5825 (11)0.151 (5)0.634 (13)
C5B0.1961 (5)0.338 (2)0.1835 (7)0.083 (4)0.366 (13)
C6B0.2144 (7)0.590 (3)0.2047 (9)0.104 (5)0.366 (13)
C18B0.8105 (6)0.998 (4)0.5629 (12)0.109 (6)0.366 (13)
C19B0.8417 (14)1.199 (3)0.579 (2)0.153 (10)0.366 (13)
H1A0.072400.574200.231100.2060*
H1B0.070200.278100.242800.2060*
H5A10.177000.265100.249200.1160*0.634 (13)
H3A0.059800.284100.022200.2160*
H3B0.055900.012200.032600.2160*
H6A20.224300.636900.142600.1150*0.634 (13)
H5A20.162000.557300.253600.1160*0.634 (13)
H2A0.019300.419000.183700.2150*
H2B0.014500.542300.112900.2150*
H6A10.239600.344000.138400.1150*0.634 (13)
H100.447900.441200.429300.0830*
H120.489401.061300.302900.0930*
H130.400401.017800.227800.0970*
H14A0.562501.109300.414900.0930*
H14B0.581900.926300.345900.0930*
H160.651301.169200.527100.0950*
H17A0.736000.978700.642800.1430*
H17B0.776300.765600.607800.1430*
H18A0.783201.263700.547900.1370*0.634 (13)
H19A0.868800.930500.606000.1820*0.634 (13)
H19B0.880501.205900.567100.1820*0.634 (13)
H4A0.117200.008700.149300.1720*
H4B0.150100.131500.077600.1720*
H70.308400.797800.188900.0970*
H90.360100.400000.353100.0850*
H5B10.201100.222900.229000.0990*0.366 (13)
H5B20.217900.272900.138800.0990*0.366 (13)
H6B10.189500.666400.244200.1250*0.366 (13)
H6B20.216400.700400.158000.1250*0.366 (13)
H18B0.826200.887300.525500.1310*0.366 (13)
H19C0.828401.316300.616400.1840*0.366 (13)
H19D0.877501.226100.554600.1840*0.366 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0905 (16)0.195 (3)0.196 (3)0.0408 (17)0.0134 (17)0.031 (2)
O20.0721 (9)0.0850 (10)0.0749 (11)0.0148 (8)0.0063 (8)0.0196 (8)
N10.1009 (18)0.141 (2)0.127 (2)0.0382 (17)0.0480 (18)0.0348 (19)
N20.0763 (14)0.164 (2)0.1018 (18)0.0213 (15)0.0260 (13)0.0395 (17)
N30.0847 (13)0.0753 (13)0.0906 (16)0.0021 (11)0.0044 (12)0.0121 (11)
N40.0861 (14)0.0884 (15)0.1015 (17)0.0078 (12)0.0030 (13)0.0022 (13)
N50.0753 (13)0.0914 (14)0.0747 (14)0.0147 (12)0.0029 (11)0.0018 (12)
C10.147 (3)0.194 (4)0.171 (4)0.033 (3)0.022 (3)0.030 (3)
C20.101 (3)0.206 (5)0.227 (5)0.006 (3)0.021 (3)0.035 (4)
C30.090 (2)0.266 (5)0.180 (4)0.035 (3)0.021 (3)0.065 (4)
C40.090 (2)0.183 (4)0.156 (3)0.008 (2)0.011 (2)0.001 (3)
C5A0.066 (3)0.141 (5)0.082 (4)0.004 (3)0.001 (3)0.001 (3)
C6A0.059 (3)0.151 (7)0.077 (5)0.011 (4)0.000 (3)0.001 (4)
C70.0742 (15)0.1012 (19)0.0670 (16)0.0125 (14)0.0008 (13)0.0074 (14)
C80.0673 (13)0.0702 (14)0.0597 (15)0.0124 (11)0.0007 (11)0.0038 (11)
C90.0664 (14)0.0790 (14)0.0680 (16)0.0028 (11)0.0048 (12)0.0050 (13)
C100.0686 (13)0.0735 (14)0.0664 (15)0.0002 (11)0.0041 (12)0.0155 (11)
C110.0681 (13)0.0658 (13)0.0594 (14)0.0053 (11)0.0024 (11)0.0016 (11)
C120.0843 (16)0.0622 (14)0.0844 (18)0.0044 (11)0.0085 (14)0.0129 (12)
C130.0953 (17)0.0662 (14)0.0785 (18)0.0044 (13)0.0104 (14)0.0156 (12)
C140.0825 (15)0.0649 (13)0.0845 (18)0.0127 (11)0.0003 (13)0.0070 (12)
C150.0676 (13)0.0558 (12)0.0697 (15)0.0082 (11)0.0032 (12)0.0023 (11)
C160.0864 (16)0.0665 (13)0.0849 (18)0.0048 (13)0.0009 (14)0.0124 (13)
C170.0904 (19)0.175 (3)0.089 (2)0.029 (2)0.0193 (17)0.002 (2)
C18A0.094 (5)0.092 (5)0.152 (6)0.016 (5)0.042 (5)0.009 (5)
C19A0.093 (6)0.206 (13)0.153 (7)0.026 (9)0.007 (5)0.020 (11)
C5B0.071 (7)0.119 (7)0.057 (6)0.029 (5)0.000 (5)0.002 (5)
C6B0.114 (10)0.128 (10)0.068 (8)0.010 (8)0.008 (6)0.006 (6)
C18B0.066 (9)0.125 (12)0.134 (9)0.009 (7)0.011 (6)0.027 (10)
C19B0.116 (17)0.127 (13)0.217 (19)0.036 (11)0.016 (14)0.018 (14)
Geometric parameters (Å, º) top
O1—C21.372 (6)C1—H1A0.9700
O1—C31.388 (5)C1—H1B0.9700
O2—C111.366 (2)C2—H2A0.9700
O2—C141.429 (3)C2—H2B0.9700
N1—C11.439 (5)C3—H3A0.9700
N1—C41.442 (5)C3—H3B0.9700
N1—C5A1.444 (8)C4—H4A0.9700
N1—C5B1.680 (12)C4—H4B0.9700
N2—C6A1.500 (8)C5A—H5A10.9700
N2—C71.242 (4)C5A—H5A20.9700
N2—C6B1.536 (16)C5B—H5B10.9700
N3—N41.309 (3)C5B—H5B20.9700
N3—C151.350 (3)C6A—H6A20.9700
N4—N51.334 (3)C6A—H6A10.9700
N5—C161.325 (3)C6B—H6B20.9700
N5—C171.462 (4)C6B—H6B10.9700
C1—C21.478 (6)C7—H70.9300
C3—C41.490 (5)C9—H90.9300
C5A—C6A1.548 (10)C10—H100.9300
C5B—C6B1.424 (19)C12—H120.9300
C7—C81.459 (3)C13—H130.9300
C8—C91.392 (3)C14—H14A0.9700
C8—C131.375 (3)C14—H14B0.9700
C9—C101.365 (3)C16—H160.9300
C10—C111.383 (3)C17—H17A0.9700
C11—C121.382 (3)C17—H17B0.9700
C12—C131.379 (3)C18A—H18A0.9300
C14—C151.471 (3)C18B—H18B0.9300
C15—C161.345 (3)C19A—H19B0.9300
C17—C18B1.432 (15)C19A—H19A0.9300
C17—C18A1.449 (10)C19B—H19C0.9300
C18A—C19A1.280 (16)C19B—H19D0.9300
C18B—C19B1.29 (3)
C2—O1—C3109.4 (3)N1—C4—H4B109.00
C11—O2—C14118.02 (17)C3—C4—H4A109.00
C1—N1—C4107.1 (3)C3—C4—H4B110.00
C1—N1—C5A102.4 (4)H4A—C4—H4B108.00
C1—N1—C5B132.7 (5)N1—C5A—H5A1110.00
C4—N1—C5A121.1 (4)N1—C5A—H5A2110.00
C4—N1—C5B94.6 (4)C6A—C5A—H5A1110.00
C6A—N2—C7116.7 (4)C6A—C5A—H5A2110.00
C6B—N2—C7112.6 (6)H5A1—C5A—H5A2108.00
N4—N3—C15108.6 (2)H5B1—C5B—H5B2109.00
N3—N4—N5107.31 (19)N1—C5B—H5B2112.00
N4—N5—C16110.0 (2)C6B—C5B—H5B1112.00
N4—N5—C17121.2 (2)N1—C5B—H5B1112.00
C16—N5—C17128.7 (2)C6B—C5B—H5B2112.00
N1—C1—C2111.5 (4)N2—C6A—H6A2111.00
O1—C2—C1112.6 (4)C5A—C6A—H6A1111.00
O1—C3—C4111.8 (4)N2—C6A—H6A1111.00
N1—C4—C3111.1 (3)C5A—C6A—H6A2111.00
N1—C5A—C6A108.0 (6)H6A1—C6A—H6A2109.00
N1—C5B—C6B100.8 (9)N2—C6B—H6B1113.00
N2—C6A—C5A104.8 (6)C5B—C6B—H6B2113.00
N2—C6B—C5B95.7 (10)N2—C6B—H6B2113.00
N2—C7—C8123.5 (2)C5B—C6B—H6B1113.00
C9—C8—C13117.5 (2)H6B1—C6B—H6B2110.00
C7—C8—C9122.3 (2)N2—C7—H7118.00
C7—C8—C13120.2 (2)C8—C7—H7118.00
C8—C9—C10121.17 (19)C10—C9—H9119.00
C9—C10—C11120.3 (2)C8—C9—H9119.00
O2—C11—C12124.47 (19)C9—C10—H10120.00
C10—C11—C12119.8 (2)C11—C10—H10120.00
O2—C11—C10115.68 (19)C11—C12—H12121.00
C11—C12—C13118.7 (2)C13—C12—H12121.00
C8—C13—C12122.5 (2)C8—C13—H13119.00
O2—C14—C15108.63 (18)C12—C13—H13119.00
C14—C15—C16130.1 (2)O2—C14—H14A110.00
N3—C15—C14122.10 (19)O2—C14—H14B110.00
N3—C15—C16107.8 (2)C15—C14—H14A110.00
N5—C16—C15106.3 (2)C15—C14—H14B110.00
N5—C17—C18A113.6 (5)H14A—C14—H14B108.00
N5—C17—C18B113.3 (8)C15—C16—H16127.00
C17—C18A—C19A121.7 (11)N5—C16—H16127.00
C17—C18B—C19B129 (2)N5—C17—H17A109.00
N1—C1—H1A109.00C18A—C17—H17B109.00
N1—C1—H1B109.00N5—C17—H17B109.00
C2—C1—H1A109.00C18A—C17—H17A109.00
C2—C1—H1B109.00C18B—C17—H17B84.00
H1A—C1—H1B108.00H17A—C17—H17B108.00
O1—C2—H2A109.00C18B—C17—H17A130.00
O1—C2—H2B109.00C19A—C18A—H18A119.00
C1—C2—H2A109.00C17—C18A—H18A119.00
C1—C2—H2B109.00C19B—C18B—H18B116.00
H2A—C2—H2B108.00C17—C18B—H18B116.00
O1—C3—H3A109.00C18A—C19A—H19B120.00
O1—C3—H3B109.00H19A—C19A—H19B120.00
C4—C3—H3A109.00C18A—C19A—H19A120.00
C4—C3—H3B109.00C18B—C19B—H19C120.00
H3A—C3—H3B108.00C18B—C19B—H19D120.00
N1—C4—H4A109.00H19C—C19B—H19D120.00
C2—O1—C3—C457.7 (5)N4—N5—C16—C150.0 (3)
C3—O1—C2—C157.7 (5)N1—C1—C2—O158.5 (5)
C14—O2—C11—C128.4 (3)O1—C3—C4—N158.5 (5)
C11—O2—C14—C15167.78 (18)N1—C5A—C6A—N2179.8 (6)
C14—O2—C11—C10170.68 (19)N2—C7—C8—C13178.0 (3)
C1—N1—C4—C355.4 (4)N2—C7—C8—C93.4 (4)
C4—N1—C5A—C6A79.1 (7)C7—C8—C13—C12178.5 (2)
C4—N1—C1—C255.3 (5)C7—C8—C9—C10178.8 (2)
C5A—N1—C1—C2176.3 (5)C9—C8—C13—C120.1 (3)
C1—N1—C5A—C6A161.9 (6)C13—C8—C9—C100.1 (3)
C5A—N1—C4—C3172.1 (5)C8—C9—C10—C110.1 (3)
C6A—N2—C7—C8167.7 (4)C9—C10—C11—C120.3 (3)
C7—N2—C6A—C5A143.5 (5)C9—C10—C11—O2179.44 (19)
C15—N3—N4—N50.4 (3)C10—C11—C12—C130.6 (3)
N4—N3—C15—C14179.4 (2)O2—C11—C12—C13179.6 (2)
N4—N3—C15—C160.4 (3)C11—C12—C13—C80.5 (3)
N3—N4—N5—C160.3 (3)O2—C14—C15—N365.1 (3)
N3—N4—N5—C17178.3 (2)O2—C14—C15—C16116.2 (3)
C17—N5—C16—C15177.8 (2)N3—C15—C16—N50.3 (3)
N4—N5—C17—C18A108.4 (5)C14—C15—C16—N5179.1 (2)
C16—N5—C17—C18A74.0 (5)N5—C17—C18A—C19A132.7 (12)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the 1,2,3-triazole ring N3–N5/C15/C16.
D—H···AD—HH···AD···AD—H···A
C6A—H6A1···Cgi0.972.903.617 (8)132
Symmetry code: (i) x+1, y1/2, 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···AD—HH···AD···AD—H···A
C6A—H6A1···Cgi0.972.903.617 (8)132
Symmetry code: (i) x+1, y1/2, 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

First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationKolb, H. C., Finn, M. G. & Sharpless, K. B. (2001). Angew. Chem. Int. Ed. 40, 2004–2021.  Web of Science CrossRef CAS Google Scholar
First citationNelson, T. D., Rosen, J. D., Brands, K. M. J., Craig, B., Huffman, M. A. & McNamara, J. M. (2004). Tetrahedron Lett. 45, 8917–8920.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationVladimirova, M. P., Simova, S. D., Stanoeva, E. R. & Mitewa, M. I. (2001). Dyes Pigm. 50, 157–162.  Web of Science CrossRef CAS Google Scholar
First citationWang, Q., Chittaboina, S. & Barnhill, H. N. (2005). Lett. Org. Chem. 2, 293–301.  Web of Science CrossRef CAS Google Scholar
First citationYu, H. X., Ma, J. F., Xu, G. H., Li, S. L., Yang, J., Liu, Y. Y. & Cheng, Y. X. (2006). J. Organomet. Chem. 691, 3531–3539.  Web of Science CSD CrossRef CAS Google Scholar

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