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Acta Cryst. (2008). E64, o1067    [ doi:10.1107/S1600536808012725 ]

4-{[1-(4-Ethoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl]diphenylmethyl}morpholine

J.-G. Wu, H.-R. Dong, H.-S. Dong and S. W. Ng

Abstract top

The title compound, C28H30N4O2, synthesized from 4-[1-(4-ethoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl]diphenylmethanol and morpholine, consists of a subsituted triazolyl group and a morpholinyl group that crowd the aliphatic C atom of a diphenylmethyl unit [Ctriaz-C-Nmorph = 110.1 (1)° and Cphenyl-C-Cphenyl = 103.9 (1)°]. The morpholine ring adopts a chair conformation.

Comment top

We have recently reported the synthesis of some (1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)diarylmethanols and characterized one of them, 1-(4-tolyl)-5-methyl-1H-1,2,3-triazol-4-yl]bis(3-chlorophenyl)methanol, by X-ray crystallography (Dong et al., 2008). In the present study, the methanolic –OH group of [1-(4-ethoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl]diphenylmethanol is replaced by a morpholinyl ring in the expectation that the resulting compound (Scheme I) will possess enhanced biological activity. The compound, C28H30N4O2 (Fig. 1), consists of a subsituted triazolyl part and a morpholinyl part that crowd the aliphatic carbon atom of the diphenylmethyl entity, the crowding depressing the Cphenyl–C–Cphenyl angle [103.9 (1)°] from the idealized angle. The morpholinyl ring adopts a chair conformation.

Related literature top

For background literature on the synthesis of precursor (1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)diarylmethanols, see: Dong et al. (2008).

Experimental top

[1-(4-Ethoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl]diphenylmethanol, which was synthesized by a modification of a published procedure (Dong et al., 2008) (1.2 g, 3.2 mmol), was dissolved in benzene (30 ml); dry hydrogen chloride gas was passed into the refluxing solution until the theoretical quantity of water was formed. Morpholine (0.4 ml) and triethylamine (0.7 ml) were added and the mixture kept at 318 K for two hours. Removal of the solvent gave a solid; this was washed with water, dried and recrystallized from ethyl acetate to give the pure compound, m.p. 456–458 K in 90% yield. The formulation was established by 1H-NMR and mass spectrosopic analyses. 1H-NMR(300 MHz, CDCl3): 1.422–1.469 (t, 3H, J = 6.9 Hz, ArOCH2–CH3), 2.049 (s, 3H, triazolyl–CH3), 2.456 (br, 4H, –N(CH2)2–), 3.829–3.859 (t, 4H, J = 4.5 Hz, –CH2OCH2–), 4.044–4.114 (q, 2H, J = 6.9 Hz, ArO–CH2–), 6.975–7.006 (d, 2H, J = 9.3 Hz, C2H5OAr–3,5H), 7.143–7.192 (t, 2H, J = 7.5 Hz, Ar–4H), 7.258–7.352 (m, 6H, C2H5OAr–2,6H, Ar–3,5H), 7.557–7.583 (d, 4H, J = 7.8 Hz, Ar–2,6H) p.p.m.. MS (%): 454 (M+., 0.88%), 369 (68), 340 (59), 312 (17), 310 (13), 264 (7.3), 252 (7.1), 224 (4.8), 219 (3.1), 205 (9.9), 191 (6.7), 178 (18), 165 (15), 162 (100), 151 (16), 149 (40), 134 (19), 121 (12), 93 (11), 91 (16), 77 (17).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5Ueq(C). The methyl groups were rotated to fit the electron density.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. 50% Probability thermal ellipsoid plot (Barbour, 2001) of C28H30N4O2. Hydrogen atoms are drawn as spheres of arbitrary radii.
4-{[1-(4-Ethoxyphenyl)-5-methyl-1H-1,2,3-triazol-4- yl]diphenylmethyl}morpholine top
Crystal data top
C28H30N4O2Z = 2
Mr = 454.56F000 = 484
Triclinic, P1Dx = 1.230 Mg m−3
Hall symbol: -P 1Melting point: 457 K
a = 9.406 (1) ÅMo Kα radiation
λ = 0.71073 Å
b = 10.125 (1) ÅCell parameters from 1386 reflections
c = 13.670 (2) Åθ = 2.3–22.5º
α = 81.408 (1)ºµ = 0.08 mm−1
β = 73.621 (1)ºT = 294 (2) K
γ = 81.547 (1)ºRhombohedron, colorless
V = 1227.4 (2) Å30.28 × 0.25 × 0.20 mm
Data collection top
Bruker APEXII
diffractometer		2830 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Monochromator: graphiteθmax = 25.0º
T = 295(2) Kθmin = 2.0º
φ and ω scansh = −7→11
Absorption correction: Nonek = −9→12
6395 measured reflectionsl = −16→16
4437 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.126  w = 1/[σ2(Fo2) + (0.0614P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
4437 reflectionsΔρmax = 0.14 e Å−3
309 parametersΔρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C28H30N4O2γ = 81.547 (1)º
Mr = 454.56V = 1227.4 (2) Å3
Triclinic, P1Z = 2
a = 9.406 (1) ÅMo Kα
b = 10.125 (1) ŵ = 0.08 mm−1
c = 13.670 (2) ÅT = 294 (2) K
α = 81.408 (1)º0.28 × 0.25 × 0.20 mm
β = 73.621 (1)º
Data collection top
Bruker APEXII
diffractometer		4437 independent reflections
Absorption correction: None2830 reflections with I > 2σ(I)
6395 measured reflectionsRint = 0.019
Refinement top
R[F2 > 2σ(F2)] = 0.046309 parameters
wR(F2) = 0.126H-atom parameters constrained
S = 0.99Δρmax = 0.14 e Å−3
4437 reflectionsΔρmin = −0.23 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1−0.01051 (14)0.78624 (14)0.99479 (11)0.0597 (4)
O21.10986 (17)0.31482 (19)0.68284 (13)0.0761 (5)
N10.43338 (16)0.39052 (15)0.83355 (11)0.0395 (4)
N20.49124 (17)0.30714 (16)0.90338 (12)0.0462 (4)
N30.59072 (17)0.21953 (16)0.85227 (11)0.0447 (4)
N40.86454 (15)0.19704 (15)0.66019 (11)0.0392 (4)
C10.31717 (19)0.49423 (18)0.86992 (14)0.0391 (5)
C20.1836 (2)0.5083 (2)0.84476 (14)0.0468 (5)
H20.16860.45210.80150.056*
C30.0710 (2)0.6066 (2)0.88424 (15)0.0479 (5)
H3−0.01880.61730.86650.057*
C40.0926 (2)0.68869 (19)0.94988 (14)0.0428 (5)
C50.2269 (2)0.6723 (2)0.97548 (15)0.0495 (5)
H50.24150.72661.02020.059*
C60.3386 (2)0.57633 (19)0.93530 (15)0.0458 (5)
H60.42900.56660.95220.055*
C7−0.1432 (2)0.8214 (2)0.96182 (15)0.0538 (6)
H7A−0.20160.74580.97830.065*
H7B−0.11890.84640.88820.065*
C8−0.2296 (3)0.9376 (2)1.01669 (19)0.0735 (7)
H8A−0.31610.96860.99200.110*
H8B−0.16791.00921.00420.110*
H8C−0.26020.90951.08910.110*
C90.4629 (2)0.4427 (2)0.64574 (15)0.0570 (6)
H9A0.44250.53500.65920.086*
H9B0.37710.41500.63290.086*
H9C0.54660.43340.58670.086*
C100.49787 (19)0.35671 (18)0.73669 (14)0.0389 (5)
C110.59709 (19)0.24503 (18)0.75005 (14)0.0372 (4)
C120.71084 (18)0.15980 (18)0.67455 (13)0.0365 (4)
C130.8762 (2)0.3413 (2)0.63607 (17)0.0545 (6)
H13A0.82340.38690.69570.065*
H13B0.83080.37710.58070.065*
C141.0384 (2)0.3658 (2)0.60466 (18)0.0663 (7)
H14A1.08930.32340.54320.080*
H14B1.04540.46170.58850.080*
C151.0936 (2)0.1761 (3)0.71158 (19)0.0702 (7)
H15A1.13950.14340.76720.084*
H15B1.14560.12670.65380.084*
C160.9328 (2)0.1497 (2)0.74525 (16)0.0557 (6)
H16A0.92610.05420.76470.067*
H16B0.88050.19640.80440.067*
C170.70954 (19)0.00784 (18)0.71035 (13)0.0381 (4)
C180.5995 (2)−0.0457 (2)0.78943 (16)0.0498 (5)
H180.52370.01180.82640.060*
C190.5992 (2)−0.1829 (2)0.81513 (17)0.0607 (6)
H190.5233−0.21630.86890.073*
C200.7093 (3)−0.2706 (2)0.76228 (17)0.0586 (6)
H200.7092−0.36290.78000.070*
C210.8192 (3)−0.2191 (2)0.68285 (17)0.0607 (6)
H210.8944−0.27710.64600.073*
C220.8196 (2)−0.0820 (2)0.65696 (16)0.0531 (5)
H220.8952−0.04910.60270.064*
C230.6762 (2)0.17581 (18)0.56946 (14)0.0398 (5)
C240.5331 (2)0.1628 (2)0.56461 (17)0.0549 (6)
H240.45770.15050.62500.066*
C250.5019 (3)0.1679 (2)0.4711 (2)0.0690 (7)
H250.40540.16050.46910.083*
C260.6119 (3)0.1836 (2)0.3817 (2)0.0746 (8)
H260.59050.18730.31890.089*
C270.7536 (3)0.1939 (2)0.38524 (17)0.0708 (7)
H270.82900.20350.32450.085*
C280.7858 (2)0.1903 (2)0.47848 (15)0.0534 (6)
H280.88260.19770.47970.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0467 (9)0.0636 (10)0.0720 (10)0.0161 (7)−0.0198 (7)−0.0315 (8)
O20.0700 (11)0.0936 (14)0.0784 (12)−0.0350 (9)−0.0273 (9)−0.0124 (10)
N10.0391 (9)0.0370 (9)0.0405 (9)0.0024 (7)−0.0088 (7)−0.0084 (7)
N20.0482 (10)0.0465 (10)0.0431 (9)0.0064 (8)−0.0137 (8)−0.0107 (8)
N30.0453 (10)0.0457 (10)0.0420 (9)0.0050 (7)−0.0114 (8)−0.0120 (8)
N40.0350 (9)0.0435 (10)0.0399 (9)−0.0056 (7)−0.0097 (7)−0.0063 (7)
C10.0363 (11)0.0372 (11)0.0418 (11)0.0000 (8)−0.0074 (8)−0.0080 (9)
C20.0460 (12)0.0499 (13)0.0486 (12)−0.0020 (9)−0.0143 (10)−0.0184 (10)
C30.0385 (11)0.0556 (14)0.0518 (12)−0.0004 (9)−0.0143 (9)−0.0139 (10)
C40.0386 (11)0.0416 (12)0.0458 (11)0.0027 (8)−0.0075 (9)−0.0115 (9)
C50.0497 (12)0.0472 (13)0.0580 (13)0.0045 (9)−0.0210 (10)−0.0230 (10)
C60.0398 (11)0.0442 (12)0.0574 (13)−0.0011 (9)−0.0173 (9)−0.0140 (10)
C70.0433 (12)0.0603 (15)0.0537 (13)0.0073 (10)−0.0133 (10)−0.0062 (11)
C80.0607 (15)0.0736 (18)0.0824 (17)0.0250 (12)−0.0215 (13)−0.0245 (14)
C90.0676 (14)0.0489 (14)0.0469 (12)0.0082 (10)−0.0117 (10)−0.0025 (10)
C100.0394 (11)0.0376 (11)0.0374 (11)−0.0010 (8)−0.0064 (8)−0.0072 (9)
C110.0357 (10)0.0387 (11)0.0381 (11)−0.0021 (8)−0.0101 (8)−0.0088 (8)
C120.0343 (10)0.0371 (11)0.0368 (10)−0.0013 (8)−0.0071 (8)−0.0075 (8)
C130.0529 (13)0.0483 (14)0.0624 (14)−0.0114 (10)−0.0118 (11)−0.0078 (11)
C140.0630 (15)0.0685 (17)0.0713 (16)−0.0269 (12)−0.0161 (13)−0.0038 (13)
C150.0514 (14)0.093 (2)0.0739 (16)−0.0184 (13)−0.0269 (12)−0.0018 (15)
C160.0476 (13)0.0729 (16)0.0506 (13)−0.0136 (10)−0.0192 (10)−0.0004 (11)
C170.0371 (10)0.0389 (11)0.0397 (11)−0.0016 (8)−0.0124 (9)−0.0072 (9)
C180.0435 (12)0.0436 (13)0.0573 (13)−0.0032 (9)−0.0037 (10)−0.0107 (10)
C190.0583 (14)0.0498 (15)0.0693 (16)−0.0149 (11)−0.0071 (12)−0.0021 (12)
C200.0746 (16)0.0380 (13)0.0671 (15)−0.0085 (11)−0.0260 (13)−0.0023 (11)
C210.0698 (15)0.0442 (14)0.0623 (14)0.0079 (11)−0.0113 (12)−0.0139 (11)
C220.0539 (13)0.0446 (13)0.0516 (13)0.0006 (9)−0.0016 (10)−0.0065 (10)
C230.0460 (11)0.0324 (11)0.0425 (11)0.0013 (8)−0.0145 (9)−0.0090 (8)
C240.0554 (14)0.0533 (14)0.0637 (14)−0.0053 (10)−0.0261 (11)−0.0110 (11)
C250.0843 (18)0.0559 (16)0.0863 (19)−0.0046 (12)−0.0538 (16)−0.0121 (13)
C260.120 (2)0.0568 (16)0.0623 (17)0.0066 (15)−0.0526 (17)−0.0146 (13)
C270.096 (2)0.0720 (18)0.0433 (13)0.0057 (14)−0.0225 (13)−0.0090 (12)
C280.0586 (14)0.0582 (14)0.0418 (12)0.0035 (10)−0.0134 (10)−0.0101 (10)
Geometric parameters (Å, °) top
O1—C41.363 (2)C12—C231.541 (2)
O1—C71.424 (2)C12—C171.544 (2)
O2—C141.414 (3)C13—C141.512 (3)
O2—C151.419 (3)C13—H13A0.9700
N1—N21.3554 (19)C13—H13B0.9700
N1—C101.364 (2)C14—H14A0.9700
N1—C11.434 (2)C14—H14B0.9700
N2—N31.3126 (19)C15—C161.504 (3)
N3—C111.368 (2)C15—H15A0.9700
N4—C131.462 (2)C15—H15B0.9700
N4—C161.469 (2)C16—H16A0.9700
N4—C121.500 (2)C16—H16B0.9700
C1—C21.376 (2)C17—C181.376 (3)
C1—C61.379 (3)C17—C221.388 (2)
C2—C31.390 (2)C18—C191.381 (3)
C2—H20.9300C18—H180.9300
C3—C41.383 (3)C19—C201.372 (3)
C3—H30.9300C19—H190.9300
C4—C51.384 (2)C20—C211.370 (3)
C5—C61.372 (2)C20—H200.9300
C5—H50.9300C21—C221.381 (3)
C6—H60.9300C21—H210.9300
C7—C81.499 (3)C22—H220.9300
C7—H7A0.9700C23—C281.378 (3)
C7—H7B0.9700C23—C241.392 (3)
C8—H8A0.9600C24—C251.382 (3)
C8—H8B0.9600C24—H240.9300
C8—H8C0.9600C25—C261.366 (3)
C9—C101.495 (2)C25—H250.9300
C9—H9A0.9600C26—C271.367 (3)
C9—H9B0.9600C26—H260.9300
C9—H9C0.9600C27—C281.385 (3)
C10—C111.381 (2)C27—H270.9300
C11—C121.525 (2)C28—H280.9300
C4—O1—C7118.54 (15)N4—C13—H13A109.7
C14—O2—C15110.11 (17)C14—C13—H13A109.7
N2—N1—C10111.22 (14)N4—C13—H13B109.7
N2—N1—C1118.18 (14)C14—C13—H13B109.7
C10—N1—C1130.58 (15)H13A—C13—H13B108.2
N3—N2—N1106.67 (14)O2—C14—C13111.94 (19)
N2—N3—C11109.81 (14)O2—C14—H14A109.2
C13—N4—C16107.06 (16)C13—C14—H14A109.2
C13—N4—C12113.90 (13)O2—C14—H14B109.2
C16—N4—C12116.16 (14)C13—C14—H14B109.2
C2—C1—C6120.09 (17)H14A—C14—H14B107.9
C2—C1—N1121.16 (16)O2—C15—C16112.19 (19)
C6—C1—N1118.67 (16)O2—C15—H15A109.2
C1—C2—C3119.83 (18)C16—C15—H15A109.2
C1—C2—H2120.1O2—C15—H15B109.2
C3—C2—H2120.1C16—C15—H15B109.2
C4—C3—C2119.99 (18)H15A—C15—H15B107.9
C4—C3—H3120.0N4—C16—C15108.98 (17)
C2—C3—H3120.0N4—C16—H16A109.9
O1—C4—C3125.11 (17)C15—C16—H16A109.9
O1—C4—C5115.37 (17)N4—C16—H16B109.9
C3—C4—C5119.51 (17)C15—C16—H16B109.9
C6—C5—C4120.41 (18)H16A—C16—H16B108.3
C6—C5—H5119.8C18—C17—C22117.13 (18)
C4—C5—H5119.8C18—C17—C12123.62 (16)
C5—C6—C1120.16 (18)C22—C17—C12119.13 (17)
C5—C6—H6119.9C17—C18—C19121.45 (18)
C1—C6—H6119.9C17—C18—H18119.3
O1—C7—C8107.35 (17)C19—C18—H18119.3
O1—C7—H7A110.2C20—C19—C18120.8 (2)
C8—C7—H7A110.2C20—C19—H19119.6
O1—C7—H7B110.2C18—C19—H19119.6
C8—C7—H7B110.2C21—C20—C19118.5 (2)
H7A—C7—H7B108.5C21—C20—H20120.7
C7—C8—H8A109.5C19—C20—H20120.7
C7—C8—H8B109.5C20—C21—C22120.7 (2)
H8A—C8—H8B109.5C20—C21—H21119.6
C7—C8—H8C109.5C22—C21—H21119.6
H8A—C8—H8C109.5C21—C22—C17121.3 (2)
H8B—C8—H8C109.5C21—C22—H22119.3
C10—C9—H9A109.5C17—C22—H22119.3
C10—C9—H9B109.5C28—C23—C24117.90 (18)
H9A—C9—H9B109.5C28—C23—C12122.05 (17)
C10—C9—H9C109.5C24—C23—C12119.77 (17)
H9A—C9—H9C109.5C25—C24—C23120.8 (2)
H9B—C9—H9C109.5C25—C24—H24119.6
N1—C10—C11104.16 (15)C23—C24—H24119.6
N1—C10—C9120.80 (16)C26—C25—C24120.4 (2)
C11—C10—C9134.81 (17)C26—C25—H25119.8
N3—C11—C10108.11 (15)C24—C25—H25119.8
N3—C11—C12119.18 (15)C25—C26—C27119.5 (2)
C10—C11—C12132.53 (16)C25—C26—H26120.2
N4—C12—C11110.13 (14)C27—C26—H26120.2
N4—C12—C23109.34 (14)C26—C27—C28120.5 (2)
C11—C12—C23112.04 (13)C26—C27—H27119.7
N4—C12—C17108.86 (13)C28—C27—H27119.7
C11—C12—C17112.32 (14)C23—C28—C27120.8 (2)
C23—C12—C17103.93 (14)C23—C28—H28119.6
N4—C13—C14109.61 (16)C27—C28—H28119.6
C10—N1—N2—N3−0.7 (2)C10—C11—C12—C23−20.6 (3)
C1—N1—N2—N3177.98 (16)N3—C11—C12—C1748.4 (2)
N1—N2—N3—C11−0.4 (2)C10—C11—C12—C17−137.1 (2)
N2—N1—C1—C2−126.47 (19)C16—N4—C13—C1460.2 (2)
C10—N1—C1—C251.9 (3)C12—N4—C13—C14−169.95 (15)
N2—N1—C1—C650.3 (2)C15—O2—C14—C1355.7 (2)
C10—N1—C1—C6−131.3 (2)N4—C13—C14—O2−59.1 (2)
C6—C1—C2—C30.9 (3)C14—O2—C15—C16−56.5 (2)
N1—C1—C2—C3177.65 (17)C13—N4—C16—C15−60.5 (2)
C1—C2—C3—C4−1.0 (3)C12—N4—C16—C15170.98 (17)
C7—O1—C4—C3−9.5 (3)O2—C15—C16—N459.9 (2)
C7—O1—C4—C5171.69 (18)N4—C12—C17—C18134.58 (18)
C2—C3—C4—O1−178.55 (18)C11—C12—C17—C1812.3 (2)
C2—C3—C4—C50.2 (3)C23—C12—C17—C18−108.97 (19)
O1—C4—C5—C6179.58 (18)N4—C12—C17—C22−49.4 (2)
C3—C4—C5—C60.7 (3)C11—C12—C17—C22−171.63 (16)
C4—C5—C6—C1−0.8 (3)C23—C12—C17—C2267.1 (2)
C2—C1—C6—C50.0 (3)C22—C17—C18—C190.5 (3)
N1—C1—C6—C5−176.83 (17)C12—C17—C18—C19176.55 (18)
C4—O1—C7—C8−175.31 (18)C17—C18—C19—C200.0 (3)
N2—N1—C10—C111.4 (2)C18—C19—C20—C21−0.4 (3)
C1—N1—C10—C11−177.04 (18)C19—C20—C21—C220.3 (3)
N2—N1—C10—C9−173.86 (17)C20—C21—C22—C170.2 (3)
C1—N1—C10—C97.7 (3)C18—C17—C22—C21−0.6 (3)
N2—N3—C11—C101.3 (2)C12—C17—C22—C21−176.84 (18)
N2—N3—C11—C12177.05 (16)N4—C12—C23—C2814.1 (2)
N1—C10—C11—N3−1.6 (2)C11—C12—C23—C28136.44 (19)
C9—C10—C11—N3172.7 (2)C17—C12—C23—C28−102.1 (2)
N1—C10—C11—C12−176.61 (18)N4—C12—C23—C24−172.18 (15)
C9—C10—C11—C12−2.3 (4)C11—C12—C23—C24−49.8 (2)
C13—N4—C12—C11−50.70 (19)C17—C12—C23—C2471.71 (19)
C16—N4—C12—C1174.41 (19)C28—C23—C24—C25−1.7 (3)
C13—N4—C12—C2372.82 (18)C12—C23—C24—C25−175.68 (18)
C16—N4—C12—C23−162.07 (15)C23—C24—C25—C261.1 (3)
C13—N4—C12—C17−174.25 (15)C24—C25—C26—C270.2 (4)
C16—N4—C12—C17−49.1 (2)C25—C26—C27—C28−0.8 (3)
N3—C11—C12—N4−73.2 (2)C24—C23—C28—C271.0 (3)
C10—C11—C12—N4101.4 (2)C12—C23—C28—C27174.90 (18)
N3—C11—C12—C23164.90 (16)C26—C27—C28—C230.2 (3)
Acknowledgements top

The authors thank the State Key Laboratory of Applied Organic Chemistry, Lanzhou University, and the University of Malaya for supporting this study.

references
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