(Z)-3-Anilino-1,3-diphenylprop-2-en-1-one

Zhang, L.-P.; Wei, L.-J.; Chen, M.-Q.; Zhang, Z.-H.

doi:10.1107/S1600536808016711

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1327

doi:10.1107/S1600536808016711

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(Z)-3-Anilino-1,3-diphenylprop-2-en-1-one

Li-Ping Zhang,^a ^* Lin-Juan Wei,^a Ming-Qing Chen ^a and Zhan-Hui Zhang ^b

^aSchool of Chemical and Materials Engineering, Jiangnan University, 1800 Lihu Road, Wuxi 214122, Jiangsu, People's Republic of China, and ^bSchool of Chemistry and Materials Science, Hebei Normal University, 113 Yuhua Road, Shijiazhuang 050000, Hebei, People's Republic of China
^*Correspondence e-mail: zhangliping76518@163.com.cn

(Received 22 May 2008; accepted 2 June 2008; online 21 June 2008)

In the title compound, C₂₁H₁₇NO, the phenyl ring directly linked to the carbonyl group is oriented at an angle of 7.3 (2)° with respect to the aniline ring, and at an angle of 55.6 (2)° with respect to the other phenyl ring. There is an intramolecular hydrogen bond involving the NH group and the carbonyl O atom. The crystal structure is stabilized by weak C—H⋯π interactions, which link the molecules into a herringbone arrangement.

Related literature

For related literature see: Dondoni & Perrone (1993 ); Ferraz et al. (1995 ); Michael et al. (2001 ); Azzaro et al. (1981 ); Alberola et al. (1999 ); Chaaban et al. (1979 ); Augusti & Kascheres (1993 ); Bejan et al. (1998 ); Eberlin & Kascheres (1988 ); Greenhill (1977 ); Michael et al. (1999 ); Elassar & El-Khair (2003 ); Zhang et al. (2006 ).

Experimental

Crystal data

C₂₁H₁₇NO
M_r = 299.36
Monoclinic, P 2₁ /c
a = 15.880 (7) Å
b = 6.034 (3) Å
c = 18.401 (8) Å
β = 114.433 (7)°
V = 1605.4 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 (2) K
0.24 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.96, T_max = 0.98
7511 measured reflections
2774 independent reflections
1580 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.249
S = 1.04
2774 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.94	2.643 (5)	138
C18—H18⋯Cgⁱ	0.93	2.84	3.627 (1)	142
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg is the centroid of the C16–C21 ring.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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/S1600536808016711/su2060sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016711/su2060Isup2.hkl

checkCIF report

Comment top

β-enamino ketones are a highly versatile class of intermediates for the synthesis of natural therapeutic and biologically active analogues (Dondoni & Perrone, 1993; Ferraz et al., 1995; Michael et al., 2001; Azzaro et al., 1981). Pyrroles, oxazoles, pyridinones, quinolines, dibenzodiazepines have also been prepared from enaminones (Alberola et al., 1999; Chaaban et al., 1979; Augusti & Kascheres, 1993; Bejan et al., 1998; Eberlin & Kascheres, 1988). It is therefore not surprising that many synthetic methods have been developed for the preparation of these compounds (Greenhill, 1977; Michael et al., 1999; Elassar & El-Khair, 2003). During our development of new environmentally friendly methodologies for the preparation of β-enamino ketones (Zhang et al., 2006), we synthesized the title compound, (I), the structure of which is reported here.

The molecular structure of compound (I) is illustrated in Fig. 1. The geometry of the enamine double bond is Z, with hydrogen bonding of the enamine N—H to the carbonyl oxygen atom (Table 1). Phenyl ring A (C1-C6) forms dihedral angles of 7.3 (2)° and 55.6 (2)° with the aniline ring C (C16-C21) and the phenyl ring B (C10-C15), respectively. As in other β-enamino ketones compound (I) displays electron delocalization, as shown by the comparison of the N1—C9 [1.347 (6)°] and N1—C16 [1.417 (6) Å] bond lengths.

The crystal structure of compound (I) is stabilized by weak C—H···π interactions, which link the molecules into a herringbone chain (Fig. 2). The distance of the H atom to the centroid of the benzene ring is 2.834 (10) Å.

Related literature top

For related literature see: Dondoni & Perrone (1993); Ferraz et al. (1995); Michael et al. (2001); Azzaro et al. (1981); Alberola et al. (1999); Chaaban et al. (1979); Augusti & Kascheres (1993); Bejan et al. (1998); Eberlin & Kascheres (1988); Greenhill (1977); Michael et al. (1999); Elassar & El-Khair (2003); Zhang et al. (2006).

Experimental top

A mixture of the 1,3-diphenylpropane-1,3-dione (5 mmol), aniline (5 mmol) and InBr₃ (0.05 mmol) was stirred at room temperature for 6 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, and then purified by column chromatography on SiO₂ with ethyl acetate-cyclohexane (1: 8), giving a yellow-orange solid (yield 68%). Mp 96–97°C; IR (neat, cm^-1): ν 3053, 1592, 1568, 1475, 1441, 1323, 1212, 1079, 1053, 1022, 904, 841, 697 ¹H NMR (CDCl₃, 300 MHz): δ 6.09 (s, 1H), 6.78 (d, 2H), 6.96–7.00 (m, 1H), 7.09–7.14 (m, 2H), 7.26–7.50 (m, 8H), 7.96 (d, 2H), 12.90 (br s, 1H, NH). ¹³C NMR (CDCl₃, 75 MHz): δ 97.0, 123.1, 124.2, 127.2, 128.2, 128.5, 128.7, 129.6, 131.3, 135.8, 139.4, 139.8, 161.4, 189.6. ESI-MS: 300 (M+1)⁺ Elemental Anal. Calcd. for C₂₁H₁₇NO: C, 84.25; H, 5.72; N, 4.68. Found: C, 84.48; H, 5.82; N, 4.45. Single crystals of (I), suitable for X-ray diffraction analysis, were obtained from ethyl acetate-cyclohexane by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 compound (I), showing the atomic numbering scheme and the displacement ellipsoids drawn at the 30% probability level. The intramolecular N-H···O hydrogen bond is shown as a dashed line.
	Fig. 2. The molecular packing of compound (I), showing the C—H···π interactions (dashed lines).

(Z)-3-Anilino-1,3-diphenylprop-2-en-1-one top

Crystal data top

C₂₁H₁₇NO	F(000) = 632
M_r = 299.36	D_x = 1.239 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1702 reflections
a = 15.880 (7) Å	θ = 2.3–23.8°
b = 6.034 (3) Å	µ = 0.08 mm⁻¹
c = 18.401 (8) Å	T = 294 K
β = 114.433 (7)°	Block, yellow
V = 1605.4 (13) Å³	0.24 × 0.20 × 0.14 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2774 independent reflections
Radiation source: fine-focus sealed tube	1580 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
phi and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→18
T_min = 0.96, T_max = 0.98	k = −7→7
7511 measured reflections	l = −17→21

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)] = 0.079	H-atom parameters constrained
wR(F²) = 0.249	w = 1/[σ²(F_o²) + (0.1119P)² + 1.614P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2774 reflections	Δρ_max = 0.24 e Å⁻³
209 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (4)

Crystal data top

C₂₁H₁₇NO	V = 1605.4 (13) Å³
M_r = 299.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.880 (7) Å	µ = 0.08 mm⁻¹
b = 6.034 (3) Å	T = 294 K
c = 18.401 (8) Å	0.24 × 0.20 × 0.14 mm
β = 114.433 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2774 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1580 reflections with I > 2σ(I)
T_min = 0.96, T_max = 0.98	R_int = 0.052
7511 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	0 restraints
wR(F²) = 0.249	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
2774 reflections	Δρ_min = −0.23 e Å⁻³
209 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	0.2315 (2)	0.0638 (5)	0.19524 (16)	0.0578 (9)
N1	0.3124 (2)	−0.1522 (6)	0.11657 (19)	0.0490 (9)
H1	0.3021	−0.1332	0.1585	0.059*
C1	0.1066 (3)	0.5369 (7)	0.0895 (2)	0.0511 (11)
H1A	0.1389	0.5646	0.0582	0.061*
C2	0.0442 (3)	0.6921 (8)	0.0932 (3)	0.0616 (13)
H2	0.0358	0.8249	0.0654	0.074*
C3	−0.0053 (3)	0.6511 (10)	0.1376 (3)	0.0723 (16)
H3	−0.0474	0.7553	0.1396	0.087*
C4	0.0075 (4)	0.4553 (11)	0.1792 (3)	0.0750 (16)
H4	−0.0267	0.4262	0.2087	0.090*
C5	0.0711 (3)	0.3018 (9)	0.1771 (3)	0.0586 (13)
H5	0.0804	0.1709	0.2061	0.070*
C6	0.1212 (3)	0.3424 (7)	0.1318 (2)	0.0430 (10)
C7	0.1904 (3)	0.1718 (7)	0.1323 (2)	0.0451 (10)
C8	0.2038 (3)	0.1350 (7)	0.0618 (2)	0.0435 (10)
H8	0.1709	0.2233	0.0177	0.052*
C9	0.2619 (3)	−0.0218 (7)	0.0543 (2)	0.0421 (10)
C10	0.2628 (3)	−0.0622 (7)	−0.0250 (2)	0.0418 (10)
C11	0.2382 (3)	−0.2677 (8)	−0.0616 (2)	0.0521 (12)
H11	0.2253	−0.3840	−0.0346	0.063*
C12	0.2325 (3)	−0.3011 (8)	−0.1375 (2)	0.0585 (13)
H12	0.2151	−0.4388	−0.1619	0.070*
C13	0.2526 (3)	−0.1323 (9)	−0.1769 (3)	0.0611 (13)
H13	0.2491	−0.1554	−0.2281	0.073*
C14	0.2776 (4)	0.0702 (9)	−0.1418 (3)	0.0690 (15)
H14	0.2913	0.1846	−0.1690	0.083*
C15	0.2828 (3)	0.1064 (8)	−0.0654 (3)	0.0587 (13)
H15	0.2997	0.2450	−0.0418	0.070*
C16	0.3797 (3)	−0.3154 (7)	0.1242 (2)	0.0458 (11)
C17	0.3834 (3)	−0.5000 (7)	0.1687 (2)	0.0536 (12)
H17	0.3408	−0.5166	0.1910	0.064*
C18	0.4486 (4)	−0.6602 (8)	0.1808 (3)	0.0679 (15)
H18	0.4510	−0.7834	0.2120	0.082*
C19	0.5104 (4)	−0.6391 (10)	0.1473 (3)	0.0804 (17)
H19	0.5539	−0.7497	0.1544	0.096*
C20	0.5083 (3)	−0.4551 (12)	0.1031 (3)	0.0783 (17)
H20	0.5509	−0.4409	0.0807	0.094*
C21	0.4432 (3)	−0.2894 (9)	0.0914 (3)	0.0647 (13)
H21	0.4424	−0.1633	0.0620	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.077 (2)	0.063 (2)	0.0374 (15)	0.0107 (17)	0.0279 (15)	0.0051 (15)
N1	0.062 (2)	0.054 (2)	0.0368 (17)	0.0121 (18)	0.0251 (17)	0.0093 (16)
C1	0.056 (3)	0.053 (3)	0.047 (2)	−0.005 (2)	0.023 (2)	−0.006 (2)
C2	0.067 (3)	0.053 (3)	0.056 (3)	0.005 (2)	0.016 (2)	−0.007 (2)
C3	0.058 (3)	0.091 (4)	0.064 (3)	0.012 (3)	0.021 (3)	−0.023 (3)
C4	0.069 (3)	0.104 (5)	0.065 (3)	0.013 (3)	0.041 (3)	−0.002 (3)
C5	0.068 (3)	0.066 (3)	0.048 (2)	0.004 (3)	0.031 (2)	0.000 (2)
C6	0.051 (2)	0.046 (2)	0.0301 (19)	−0.0043 (19)	0.0157 (18)	−0.0060 (17)
C7	0.051 (2)	0.047 (3)	0.040 (2)	−0.005 (2)	0.0211 (19)	−0.0032 (19)
C8	0.054 (2)	0.047 (2)	0.0299 (19)	0.002 (2)	0.0177 (18)	0.0031 (18)
C9	0.050 (2)	0.044 (2)	0.0333 (19)	−0.001 (2)	0.0178 (18)	0.0006 (18)
C10	0.047 (2)	0.045 (2)	0.0315 (19)	0.0042 (19)	0.0152 (18)	0.0012 (17)
C11	0.070 (3)	0.050 (3)	0.041 (2)	−0.006 (2)	0.028 (2)	−0.004 (2)
C12	0.071 (3)	0.061 (3)	0.044 (2)	−0.004 (2)	0.024 (2)	−0.015 (2)
C13	0.078 (3)	0.073 (4)	0.038 (2)	0.012 (3)	0.029 (2)	0.003 (2)
C14	0.104 (4)	0.067 (4)	0.051 (3)	0.009 (3)	0.046 (3)	0.017 (3)
C15	0.094 (4)	0.046 (3)	0.047 (2)	0.000 (2)	0.040 (3)	0.004 (2)
C16	0.048 (2)	0.051 (3)	0.033 (2)	0.002 (2)	0.0113 (18)	−0.0049 (18)
C17	0.055 (3)	0.049 (3)	0.045 (2)	−0.004 (2)	0.008 (2)	−0.003 (2)
C18	0.068 (3)	0.042 (3)	0.068 (3)	0.004 (3)	0.002 (3)	0.002 (2)
C19	0.068 (4)	0.076 (4)	0.078 (4)	0.024 (3)	0.011 (3)	−0.012 (3)
C20	0.057 (3)	0.114 (5)	0.064 (3)	0.016 (3)	0.025 (3)	−0.003 (3)
C21	0.056 (3)	0.084 (4)	0.056 (3)	0.007 (3)	0.024 (2)	0.006 (3)

Geometric parameters (Å, º) top

O1—C7	1.252 (5)	C10—C11	1.388 (6)
N1—C9	1.347 (5)	C11—C12	1.377 (6)
N1—C16	1.416 (5)	C11—H11	0.9300
N1—H1	0.8600	C12—C13	1.362 (6)
C1—C6	1.373 (6)	C12—H12	0.9300
C1—C2	1.386 (6)	C13—C14	1.362 (7)
C1—H1A	0.9300	C13—H13	0.9300
C2—C3	1.369 (7)	C14—C15	1.391 (6)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.377 (8)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.369 (6)
C4—C5	1.382 (7)	C16—C21	1.384 (6)
C4—H4	0.9300	C17—C18	1.366 (7)
C5—C6	1.393 (6)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.363 (8)
C6—C7	1.502 (6)	C18—H18	0.9300
C7—C8	1.416 (5)	C19—C20	1.369 (8)
C8—C9	1.368 (6)	C19—H19	0.9300
C8—H8	0.9300	C20—C21	1.389 (7)
C9—C10	1.486 (5)	C20—H20	0.9300
C10—C15	1.372 (6)	C21—H21	0.9300

C9—N1—C16	130.5 (3)	C12—C11—C10	120.6 (4)
C9—N1—H1	114.7	C12—C11—H11	119.7
C16—N1—H1	114.7	C10—C11—H11	119.7
C6—C1—C2	120.4 (4)	C13—C12—C11	119.9 (4)
C6—C1—H1A	119.8	C13—C12—H12	120.0
C2—C1—H1A	119.8	C11—C12—H12	120.0
C3—C2—C1	120.4 (5)	C12—C13—C14	120.3 (4)
C3—C2—H2	119.8	C12—C13—H13	119.8
C1—C2—H2	119.8	C14—C13—H13	119.8
C2—C3—C4	119.8 (5)	C13—C14—C15	120.2 (4)
C2—C3—H3	120.1	C13—C14—H14	119.9
C4—C3—H3	120.1	C15—C14—H14	119.9
C3—C4—C5	120.1 (5)	C10—C15—C14	120.1 (4)
C3—C4—H4	120.0	C10—C15—H15	120.0
C5—C4—H4	120.0	C14—C15—H15	120.0
C4—C5—C6	120.3 (5)	C17—C16—C21	119.7 (4)
C4—C5—H5	119.9	C17—C16—N1	118.0 (4)
C6—C5—H5	119.9	C21—C16—N1	122.3 (4)
C1—C6—C5	119.0 (4)	C18—C17—C16	121.1 (5)
C1—C6—C7	122.8 (4)	C18—C17—H17	119.5
C5—C6—C7	118.3 (4)	C16—C17—H17	119.5
O1—C7—C8	123.2 (4)	C19—C18—C17	119.9 (5)
O1—C7—C6	117.5 (3)	C19—C18—H18	120.0
C8—C7—C6	119.3 (4)	C17—C18—H18	120.0
C9—C8—C7	124.4 (4)	C18—C19—C20	120.0 (5)
C9—C8—H8	117.8	C18—C19—H19	120.0
C7—C8—H8	117.8	C20—C19—H19	120.0
N1—C9—C8	120.4 (3)	C19—C20—C21	120.6 (5)
N1—C9—C10	119.7 (4)	C19—C20—H20	119.7
C8—C9—C10	119.6 (3)	C21—C20—H20	119.7
C15—C10—C11	118.8 (4)	C16—C21—C20	118.7 (5)
C15—C10—C9	120.6 (4)	C16—C21—H21	120.6
C11—C10—C9	120.5 (4)	C20—C21—H21	120.6

C6—C1—C2—C3	−1.5 (7)	N1—C9—C10—C11	56.6 (6)
C1—C2—C3—C4	0.4 (7)	C8—C9—C10—C11	−117.8 (5)
C2—C3—C4—C5	0.9 (8)	C15—C10—C11—C12	−0.9 (7)
C3—C4—C5—C6	−1.2 (7)	C9—C10—C11—C12	175.3 (4)
C2—C1—C6—C5	1.2 (6)	C10—C11—C12—C13	1.0 (7)
C2—C1—C6—C7	−177.8 (4)	C11—C12—C13—C14	−0.4 (8)
C4—C5—C6—C1	0.2 (6)	C12—C13—C14—C15	−0.1 (8)
C4—C5—C6—C7	179.2 (4)	C11—C10—C15—C14	0.3 (7)
C1—C6—C7—O1	146.2 (4)	C9—C10—C15—C14	−175.9 (4)
C5—C6—C7—O1	−32.8 (6)	C13—C14—C15—C10	0.2 (8)
C1—C6—C7—C8	−35.9 (6)	C9—N1—C16—C17	−143.8 (4)
C5—C6—C7—C8	145.0 (4)	C9—N1—C16—C21	38.9 (7)
O1—C7—C8—C9	0.5 (7)	C21—C16—C17—C18	−0.4 (6)
C6—C7—C8—C9	−177.2 (4)	N1—C16—C17—C18	−177.7 (4)
C16—N1—C9—C8	−176.4 (4)	C16—C17—C18—C19	−1.1 (7)
C16—N1—C9—C10	9.3 (7)	C17—C18—C19—C20	1.6 (8)
C7—C8—C9—N1	−1.0 (6)	C18—C19—C20—C21	−0.5 (8)
C7—C8—C9—C10	173.4 (4)	C17—C16—C21—C20	1.4 (7)
N1—C9—C10—C15	−127.2 (5)	N1—C16—C21—C20	178.6 (4)
C8—C9—C10—C15	58.4 (6)	C19—C20—C21—C16	−0.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.94	2.643 (5)	138
C18—H18···Cgⁱ	0.93	2.84	3.627 (1)	142

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇NO
M_r	299.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	15.880 (7), 6.034 (3), 18.401 (8)
β (°)	114.433 (7)
V (Å³)	1605.4 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.96, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	7511, 2774, 1580
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.249, 1.05
No. of reflections	2774
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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···O1	0.86	1.94	2.643 (5)	138
C18—H18···Cgⁱ	0.93	2.84	3.627 (1)	142

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

Acknowledgements

This work was supported financially by Jiangnan University.

References

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