(Z)-3-(4-Methoxy­anilino)-1-phenyl­but-2-en-1-one

Zhang, L.-P.; Yang, M.; Fang, Y.

doi:10.1107/S1600536809051186

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o7

doi:10.1107/S1600536809051186

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(Z)-3-(4-Methoxyanilino)-1-phenylbut-2-en-1-one

Li-Ping Zhang,^a ^* Ming Yang ^a and Yun Fang ^a

^aSchool of Chemical and Materials Engineering, Jiangnan University, 1800 Lihu Road, Wuxi 214122, Jiangsu, People's Republic of China
^*Correspondence e-mail: zlp609@qq.com

(Received 20 November 2009; accepted 27 November 2009; online 4 December 2009)

In the title compound, C₁₇H₁₇NO₂, the dihedral angle between the two benzene rings is 6.9 (1)°. The methoxy group is twisted slightly away from the aniline ring [C—O—C—C = 12.2 (3)°]. An intramolecular N—H⋯O hydrogen bond generating an S(6) ring is observed. The crystal packing is stabilized by weak C—H⋯O and C—H⋯π interactions, forming a two-dimensional network.

Related literature

For the biological activity of β-enamino ketones, see: Azzaro et al. (1981 ); Dannhardt et al. (1998 ); Boger et al. (1989 ); Wang et al. (1982 ). For the preparation of β-enamino ketones, see: Greenhill (1977 ); Elassar & El-Khair (2003 ); Zhang et al. (2006 ).

Experimental

Crystal data

C₁₇H₁₇NO₂
M_r = 267.32
Monoclinic, P 2₁ /n
a = 6.435 (2) Å
b = 7.287 (3) Å
c = 30.919 (12) Å
β = 94.954 (6)°
V = 1444.5 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 K
0.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.739, T_max = 1.000
7729 measured reflections
2931 independent reflections
1900 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.135
S = 1.00
2931 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.91	2.629 (2)	139
C8—H8B⋯O2ⁱ	0.96	2.49	3.351 (3)	148
C3—H3⋯Cg2ⁱⁱ	0.93	2.84	3.712 (3)	156
C13—H13⋯Cg1ⁱⁱⁱ	0.93	2.82	3.619 (3)	145
Symmetry codes: (i) x+1, y, z; (ii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 rings, respectively.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051186/ci2973sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051186/ci2973Isup2.hkl

checkCIF report

Comment top

β-enamino ketones have attracted considerable interest, because they are versatile intermediates for the synthesis of natural therapeutic and biologically active analogues including anticonvulsant (Azzaro et al., 1981), anti-inflammatory (Dannhardt et al., 1998) and antitumor agents (Boger et al., 1989), as well as quinolone antibacterials (Wang et al., 1982). It is therefore not surprising that many synthetic methods have been developed for the preparation of these compounds (Greenhill et al., 1977; Elassar et al., 2003). During the development of new environmental friendly methodologies (Zhang et al., 2006) for the preparation of β-enamino ketones, we synthesized the title compound (Fig.1) and its crystal structure is reported here.

In the title compound, the dihedral angle between the two benzene rings is 6.9 (1)%. The methoxy group is slightly twisted away from the aniline ring, with a C7—O1—C4—C3 torsion angle of 12.2 (3)°. The C10—C11 bond length [1.415 (2) Å] is shorter than the C11—C12 bond length [1.500 (2) Å], and the N1—C9 bond length [1.333 (2) Å] is markedly shorter than the N1—C1 [1.419 (2) Å] bond length, indicating a strong electron delocalization. An intramolecular N1—H1···O2 hydrogen bond observed.

The crystal packing is stabilized by weak C—H···O and C—H···π interactions. Intermolecular C8—H8B···O2 hydrogen bonds link the molecules into a C(6) chain propagating along the a axis (Fig.2). In addition, the crystal packing is stabilized by C—H···π interactions; these interactions link the chains along the b axis, forming a two-dimensional network (Fig.2).

Related literature top

For the biological activity of β-enamino ketones, see: Azzaro et al. (1981); Dannhardt et al. (1998); Boger et al. (1989); Wang et al. (1982). For the preparation of β-enamino ketones, see: Greenhill et al. (1977); Elassar et al. (2003); Zhang et al. (2006). Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 rings, respectively.

Experimental top

A mixture of 1-phenylbutane-1,3-dione (5 mmol), 4-methoxybenzenamine (5 mmol) and InBr₃ (0.05 mmol) was stirred at room temperature for 1 h. After completion of the reaction, the reaction mixture was diluted with H₂O (10 ml) and extracted with EtOAc (210 ml). The combined organic layers were dried, concentrated, purified by column chromatography on SiO₂ with ethyl acetate-cyclohexane (2:8), to obatin a pale yellow solid, with a yield of 78% (m. p. 84–85° C); IR (neat):ν 2979, 2870,1608, 1576, 1504, 1473, 1432,1372, 820, 744 cm^-1; ¹H NMR(CDCl₃, 300 MHz): δ 2.06(s, 3H), 3.80(s, 3H), 5.86(s, 1H), 6.88(d, 2H,Ar—H), 7.09(d, 2H,Ar—H), 7.42–7.45(m, 3H,Ph), 7.89–7.92 (m, 2H, Ph), 12.92 (br s, 1H, NH). ¹³C NMR(CDCl₃, 75 MHz): δ 20.2, 63.7, 93.5, 114.8, 126.5, 127.0, 128.2, 130.7, 131.3, 140.1, 157.2, 163.1, 188.3. ESI-MS: 268(M+1)⁺. Analysis calculated for C₁₇H₁₇NO₂: C 76.38, H 6.41, N 5.24; found: C 76.53, H 6.52, N 5.32. Single crystals suitable for X-ray diffraction study were obtained from ethyl acetate-cyclohexane by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of the title compound, showing C—H···O hydrogen-bonded (dashed lines) chains along the a axis.

(Z)-3-(4-Methoxyanilino)-1-phenylbut-2-en-1-one top

Crystal data top

C₁₇H₁₇NO₂	F(000) = 568
M_r = 267.32	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2333 reflections
a = 6.435 (2) Å	θ = 2.6–26.3°
b = 7.287 (3) Å	µ = 0.08 mm⁻¹
c = 30.919 (12) Å	T = 294 K
β = 94.954 (6)°	Block, yellow
V = 1444.5 (9) Å³	0.24 × 0.20 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2931 independent reflections
Radiation source: fine-focus sealed tube	1900 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→8
T_min = 0.739, T_max = 1.000	k = −9→7
7729 measured reflections	l = −34→38

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0645P)² + 0.2627P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2931 reflections	Δρ_max = 0.18 e Å⁻³
184 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (3)

Crystal data top

C₁₇H₁₇NO₂	V = 1444.5 (9) Å³
M_r = 267.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.435 (2) Å	µ = 0.08 mm⁻¹
b = 7.287 (3) Å	T = 294 K
c = 30.919 (12) Å	0.24 × 0.20 × 0.16 mm
β = 94.954 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2931 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1900 reflections with I > 2σ(I)
T_min = 0.739, T_max = 1.000	R_int = 0.036
7729 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
2931 reflections	Δρ_min = −0.17 e Å⁻³
184 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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	0.0332 (2)	0.1669 (2)	0.45901 (4)	0.0621 (4)
O2	−0.17087 (19)	0.1729 (2)	0.20705 (4)	0.0552 (4)
N1	0.0723 (2)	0.1693 (2)	0.27987 (4)	0.0417 (4)
H1	−0.0489	0.1722	0.2658	0.050*
C1	0.0705 (2)	0.1739 (2)	0.32573 (5)	0.0364 (4)
C2	−0.0759 (3)	0.2824 (3)	0.34338 (5)	0.0412 (4)
H2	−0.1639	0.3558	0.3253	0.049*
C3	−0.0940 (3)	0.2835 (3)	0.38775 (5)	0.0445 (5)
H3	−0.1947	0.3560	0.3992	0.053*
C4	0.0378 (3)	0.1768 (2)	0.41473 (5)	0.0423 (4)
C5	0.1869 (3)	0.0706 (3)	0.39734 (6)	0.0515 (5)
H5	0.2780	0.0005	0.4156	0.062*
C6	0.2022 (3)	0.0673 (3)	0.35319 (6)	0.0480 (5)
H6	0.3015	−0.0069	0.3418	0.058*
C7	−0.1412 (4)	0.2438 (4)	0.47712 (6)	0.0798 (8)
H7A	−0.1385	0.3749	0.4740	0.120*
H7B	−0.1366	0.2126	0.5074	0.120*
H7C	−0.2670	0.1963	0.4623	0.120*
C8	0.4516 (3)	0.1682 (3)	0.27522 (6)	0.0504 (5)
H8A	0.4579	0.2429	0.3009	0.076*
H8B	0.5399	0.2199	0.2549	0.076*
H8C	0.4981	0.0463	0.2828	0.076*
C9	0.2316 (3)	0.1612 (2)	0.25509 (5)	0.0384 (4)
C10	0.1947 (3)	0.1546 (2)	0.21040 (5)	0.0397 (4)
H10	0.3087	0.1449	0.1940	0.048*
C11	−0.0069 (3)	0.1616 (2)	0.18819 (5)	0.0386 (4)
C12	−0.0272 (3)	0.1643 (2)	0.13949 (5)	0.0390 (4)
C13	0.1114 (3)	0.0745 (3)	0.11502 (5)	0.0485 (5)
H13	0.2218	0.0086	0.1288	0.058*
C14	0.0869 (3)	0.0820 (3)	0.07020 (6)	0.0592 (6)
H14	0.1797	0.0195	0.0540	0.071*
C15	−0.0728 (4)	0.1807 (3)	0.04946 (6)	0.0612 (6)
H15	−0.0872	0.1869	0.0193	0.073*
C16	−0.2117 (4)	0.2703 (3)	0.07320 (6)	0.0621 (6)
H16	−0.3203	0.3375	0.0591	0.075*
C17	−0.1908 (3)	0.2612 (3)	0.11809 (6)	0.0525 (5)
H17	−0.2871	0.3205	0.1340	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0685 (10)	0.0814 (11)	0.0370 (7)	0.0231 (8)	0.0080 (6)	0.0056 (7)
O2	0.0377 (7)	0.0836 (11)	0.0449 (7)	−0.0037 (7)	0.0074 (6)	−0.0087 (7)
N1	0.0333 (8)	0.0548 (10)	0.0370 (8)	−0.0018 (7)	0.0037 (6)	−0.0034 (7)
C1	0.0366 (9)	0.0376 (10)	0.0348 (9)	−0.0016 (7)	0.0027 (7)	−0.0008 (7)
C2	0.0355 (9)	0.0476 (11)	0.0399 (10)	0.0068 (8)	−0.0001 (7)	0.0040 (8)
C3	0.0426 (10)	0.0488 (12)	0.0429 (10)	0.0107 (8)	0.0082 (8)	−0.0013 (8)
C4	0.0476 (10)	0.0462 (11)	0.0329 (9)	0.0030 (8)	0.0031 (8)	0.0010 (8)
C5	0.0565 (12)	0.0516 (12)	0.0463 (11)	0.0195 (10)	0.0038 (9)	0.0093 (9)
C6	0.0557 (11)	0.0438 (11)	0.0456 (11)	0.0178 (9)	0.0100 (8)	0.0023 (9)
C7	0.0960 (18)	0.102 (2)	0.0442 (12)	0.0378 (15)	0.0206 (12)	0.0024 (12)
C8	0.0375 (10)	0.0637 (13)	0.0498 (11)	0.0002 (9)	0.0039 (8)	0.0037 (9)
C9	0.0368 (9)	0.0355 (10)	0.0434 (10)	−0.0023 (7)	0.0066 (7)	0.0012 (8)
C10	0.0372 (9)	0.0442 (11)	0.0388 (9)	−0.0009 (8)	0.0098 (7)	0.0003 (8)
C11	0.0404 (10)	0.0363 (10)	0.0398 (9)	−0.0036 (8)	0.0082 (8)	−0.0024 (8)
C12	0.0424 (10)	0.0361 (10)	0.0384 (9)	−0.0062 (8)	0.0023 (7)	−0.0024 (8)
C13	0.0552 (12)	0.0484 (12)	0.0425 (11)	0.0028 (9)	0.0071 (8)	−0.0012 (9)
C14	0.0729 (14)	0.0622 (14)	0.0439 (11)	−0.0019 (11)	0.0137 (10)	−0.0078 (10)
C15	0.0862 (16)	0.0605 (14)	0.0358 (10)	−0.0136 (12)	−0.0008 (10)	−0.0006 (10)
C16	0.0730 (14)	0.0571 (14)	0.0526 (12)	0.0022 (11)	−0.0148 (10)	0.0031 (10)
C17	0.0555 (12)	0.0505 (12)	0.0505 (12)	0.0040 (10)	−0.0016 (9)	−0.0073 (10)

Geometric parameters (Å, º) top

O1—C4	1.374 (2)	C8—C9	1.497 (2)
O1—C7	1.413 (2)	C8—H8A	0.96
O2—C11	1.251 (2)	C8—H8B	0.96
N1—C9	1.333 (2)	C8—H8C	0.96
N1—C1	1.419 (2)	C9—C10	1.383 (2)
N1—H1	0.86	C10—C11	1.415 (2)
C1—C2	1.378 (2)	C10—H10	0.93
C1—C6	1.385 (2)	C11—C12	1.500 (2)
C2—C3	1.387 (2)	C12—C13	1.383 (2)
C2—H2	0.93	C12—C17	1.387 (3)
C3—C4	1.378 (2)	C13—C14	1.382 (2)
C3—H3	0.93	C13—H13	0.93
C4—C5	1.378 (2)	C14—C15	1.368 (3)
C5—C6	1.377 (2)	C14—H14	0.93
C5—H5	0.93	C15—C16	1.370 (3)
C6—H6	0.93	C15—H15	0.93
C7—H7A	0.96	C16—C17	1.385 (3)
C7—H7B	0.96	C16—H16	0.93
C7—H7C	0.96	C17—H17	0.93

C4—O1—C7	117.43 (15)	C9—C8—H8C	109.5
C9—N1—C1	130.43 (15)	H8A—C8—H8C	109.5
C9—N1—H1	114.8	H8B—C8—H8C	109.5
C1—N1—H1	114.8	N1—C9—C10	120.13 (16)
C2—C1—C6	118.82 (15)	N1—C9—C8	120.40 (15)
C2—C1—N1	118.30 (15)	C10—C9—C8	119.40 (15)
C6—C1—N1	122.79 (15)	C9—C10—C11	123.68 (15)
C1—C2—C3	120.92 (16)	C9—C10—H10	118.2
C1—C2—H2	119.5	C11—C10—H10	118.2
C3—C2—H2	119.5	O2—C11—C10	123.41 (16)
C4—C3—C2	119.71 (16)	O2—C11—C12	117.59 (15)
C4—C3—H3	120.1	C10—C11—C12	118.94 (14)
C2—C3—H3	120.1	C13—C12—C17	118.60 (16)
O1—C4—C5	115.81 (15)	C13—C12—C11	122.58 (16)
O1—C4—C3	124.58 (16)	C17—C12—C11	118.82 (16)
C5—C4—C3	119.61 (16)	C14—C13—C12	120.45 (18)
C6—C5—C4	120.56 (17)	C14—C13—H13	119.8
C6—C5—H5	119.7	C12—C13—H13	119.8
C4—C5—H5	119.7	C15—C14—C13	120.44 (19)
C5—C6—C1	120.36 (17)	C15—C14—H14	119.8
C5—C6—H6	119.8	C13—C14—H14	119.8
C1—C6—H6	119.8	C14—C15—C16	119.87 (18)
O1—C7—H7A	109.5	C14—C15—H15	120.1
O1—C7—H7B	109.5	C16—C15—H15	120.1
H7A—C7—H7B	109.5	C15—C16—C17	120.2 (2)
O1—C7—H7C	109.5	C15—C16—H16	119.9
H7A—C7—H7C	109.5	C17—C16—H16	119.9
H7B—C7—H7C	109.5	C16—C17—C12	120.42 (18)
C9—C8—H8A	109.5	C16—C17—H17	119.8
C9—C8—H8B	109.5	C12—C17—H17	119.8
H8A—C8—H8B	109.5

C9—N1—C1—C2	142.48 (19)	N1—C9—C10—C11	2.1 (3)
C9—N1—C1—C6	−40.9 (3)	C8—C9—C10—C11	−175.06 (16)
C6—C1—C2—C3	−0.9 (3)	C9—C10—C11—O2	−0.6 (3)
N1—C1—C2—C3	175.86 (16)	C9—C10—C11—C12	176.46 (16)
C1—C2—C3—C4	0.9 (3)	O2—C11—C12—C13	−149.89 (18)
C7—O1—C4—C5	−167.8 (2)	C10—C11—C12—C13	32.8 (2)
C7—O1—C4—C3	12.2 (3)	O2—C11—C12—C17	30.3 (2)
C2—C3—C4—O1	−179.76 (17)	C10—C11—C12—C17	−146.95 (18)
C2—C3—C4—C5	0.3 (3)	C17—C12—C13—C14	0.2 (3)
O1—C4—C5—C6	178.64 (18)	C11—C12—C13—C14	−179.60 (17)
C3—C4—C5—C6	−1.4 (3)	C12—C13—C14—C15	1.0 (3)
C4—C5—C6—C1	1.4 (3)	C13—C14—C15—C16	−1.1 (3)
C2—C1—C6—C5	−0.2 (3)	C14—C15—C16—C17	0.0 (3)
N1—C1—C6—C5	−176.83 (17)	C15—C16—C17—C12	1.2 (3)
C1—N1—C9—C10	178.77 (16)	C13—C12—C17—C16	−1.3 (3)
C1—N1—C9—C8	−4.1 (3)	C11—C12—C17—C16	178.51 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.91	2.629 (2)	139
C8—H8B···O2ⁱ	0.96	2.49	3.351 (3)	148
C3—H3···Cg2ⁱⁱ	0.93	2.84	3.712 (3)	156
C13—H13···Cg1ⁱⁱⁱ	0.93	2.82	3.619 (3)	145

Symmetry codes: (i) x+1, y, z; (ii) −x−1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₂
M_r	267.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	6.435 (2), 7.287 (3), 30.919 (12)
β (°)	94.954 (6)
V (Å³)	1444.5 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.739, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7729, 2931, 1900
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.135, 1.00
No. of reflections	2931
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.91	2.629 (2)	139
C8—H8B···O2ⁱ	0.96	2.49	3.351 (3)	148
C3—H3···Cg2ⁱⁱ	0.93	2.84	3.712 (3)	156
C13—H13···Cg1ⁱⁱⁱ	0.93	2.82	3.619 (3)	145

Symmetry codes: (i) x+1, y, z; (ii) −x−1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

This work was supported financially by Jiangnan University.

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