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

Zhang, L.-P.; Qi, L.-Y.; Fang, Y.

doi:10.1107/S1600536810004460

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o576

doi:10.1107/S1600536810004460

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

Li-Ping Zhang,^a Li-Yun Qi ^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 2 December 2009; accepted 4 February 2010; online 10 February 2010)

In the title compound, C₁₇H₁₇NO₂, the dihedral angle between the two benzene rings is 55.2 (2)°. The methoxy group is slightly twisted away from the aniline ring [dihedral angle = 10.3 (2)°]. An intramolecular N—H⋯O interaction is present. In the crystal, the molecules are linked into a three-dimensional supramolecular network through two sets of C—H⋯π interactions.

Related literature

For the use of β-enamino ketones as intermediates for the synthesis of natural therapeutic and biologically active analogues, see:Azzaro et al. (1981 ); Dannhardt et al. (1998 ); Boger et al. (1989 ); Wang et al. (1982 ). For the synthesis of β-enamino ketones, see: Greenhill et al. (1977 ); Elassar & El-Khair (2003 ); Zhang et al. (2006 ).

Experimental

Crystal data

C₁₇H₁₇NO₂
M_r = 267.32
Tetragonal, P 4₂ /n
a = 19.125 (2) Å
c = 7.9993 (19) Å
V = 2925.9 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 K
0.20 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.984, T_max = 0.992
15499 measured reflections
3001 independent reflections
1457 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.115
S = 1.02
3001 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring. C13 is the nearest aromatic atom to H16.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.91	2.639 (2)	139
C3—H3⋯Cg1ⁱ	0.93	2.79	3.725 (2)	153
C16—H16⋯π(C13)ⁱⁱ	0.93	2.78	3.688 (4)	167
Symmetry codes: (i) $[-y+{\script{3\over 2}}, x, -z-{\script{1\over 2}}]$ ; (ii) $[-y+1, x+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536810004460/bv2137sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004460/bv2137Isup2.hkl

checkCIF report

Comment top

β-Enamino ketones have attracted much interest because they are versatile intermediates for the synthesis of natural therapeutic and biologically active analogues including taxo anticonvulsivant (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). In our developing new environmental friendly methodologies (Zhang et al., 2006) for the preparation of β-enamino ketones, we synthesized the title compound (I) (Fig.1), the synthesis and crystal structure of which are reported here.

In the title compound, the ring C1—C6 forms dihedral angles of 10.3 (2)° and 124.8 (2)°, respectively, with the C7—O1—C2 methoxy group and the C12—C17. The bond lengths C10—C11 [1.417 (3) Å] and N1—C9 [1.349 (2) Å] are slightly shorter than corresponding C11—C12 [1.497 (3) Å], and N1—C1[1.404 (2) Å], indicating a weak electron delocalization.

In the crystal, each four centrosymmetry related molecules are linked by C3—H1—Cg1 interactions into a four-leaves windmill (Fig.2), which are further linked into a three-dimensional supramolecular network by C16—H16—Cg2 interactions(Fig.3). The C—H···π distance is 2.79Å for C3—H1—Cg1 (Cg1: C1/C2—C3), with an angle of 152.8 (2)° and 2.78%A for C16—H16—Cg13 with an angle of 166.5 (3)°.

Related literature top

For the use of β-enamino ketones as intermediates for the synthesis of natural therapeutic and biologically active analogues, see:Azzaro et al. (1981); Dannhardt et al. (1998); Boger et al. (1989); Wang et al. (1982). For synthetic methods for the preparation of β-enamino ketones, see: Greenhill et al. (1977); Elassar et al. (2003); Zhang et al. (2006).

Experimental top

A mixture of the 1-phenylbutane-1,3-dione (5 mmol), 2-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). A pale yellow solid was obtained, with a yield of 83%. mp 92–93οC; IR (neat):ν 3006, 1608, 1477, 1461, 1373, 1284,1119,1024, 748 cm^-1; ¹H NMR(CDCl₃, 300 MHz): δ 2.14(s, 3H), 3.90(s, 3H), 5.91(s, 1H), 6.92–6.97(d, 2H,Ar—H), 7.17–7.22(m, 2H,Ar—H), 7.41–7.45(m, 3H,Ph), 7.91–7.94 (m, 2H, Ph), 12.87 (br s, 1H, NH). ¹³C NMR(CDCl₃, 75 MHz): δ 20.4, 55.8, 94.4,111.4, 120.4, 125.3, 126.6, 127.1,128.1, 130.7,140.2,153.0, 162.3, 188.5. ESI-MS: 268(M+1)⁺ Anal. Calcd for C₁₇H₁₇NO₂: C,76.38; H,6.41;N,5.24. Found:C,76.56; H,6.28; N,5.35.

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.
	Fig. 2. The intermolecular C—H···π interactions between aromatic rings of adjacent molecules.
	Fig. 3. The molecular packing of the title compound, showing the C—H···π three-dimensional supramolecular network.

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

Crystal data top

C₁₇H₁₇NO₂	D_x = 1.214 Mg m⁻³
M_r = 267.32	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₂/n	Cell parameters from 2401 reflections
Hall symbol: -P 4bc	θ = 2.8–21.2°
a = 19.125 (2) Å	µ = 0.08 mm⁻¹
c = 7.9993 (19) Å	T = 294 K
V = 2925.9 (8) Å³	Block, colorless
Z = 8	0.20 × 0.12 × 0.10 mm
F(000) = 1136

Data collection top

Bruker SMART CCD area-detector diffractometer	3001 independent reflections
Radiation source: fine-focus sealed tube	1457 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ω scans	θ_max = 26.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→23
T_min = 0.984, T_max = 0.992	k = −23→12
15499 measured reflections	l = −10→9

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0385P)² + 0.433P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3001 reflections	Δρ_max = 0.13 e Å⁻³
184 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0090 (9)

Crystal data top

C₁₇H₁₇NO₂	Z = 8
M_r = 267.32	Mo Kα radiation
Tetragonal, P4₂/n	µ = 0.08 mm⁻¹
a = 19.125 (2) Å	T = 294 K
c = 7.9993 (19) Å	0.20 × 0.12 × 0.10 mm
V = 2925.9 (8) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3001 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1457 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.992	R_int = 0.067
15499 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.02	Δρ_max = 0.13 e Å⁻³
3001 reflections	Δρ_min = −0.12 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	0.66062 (7)	0.61242 (9)	0.03020 (19)	0.0750 (5)
O2	0.50749 (8)	0.65620 (8)	0.22101 (19)	0.0700 (5)
N1	0.53344 (8)	0.60548 (8)	−0.0795 (2)	0.0544 (5)
H1	0.5444	0.6304	0.0061	0.065*
C1	0.58654 (11)	0.59997 (10)	−0.1999 (3)	0.0518 (5)
C2	0.65502 (11)	0.60408 (11)	−0.1391 (3)	0.0571 (6)
C3	0.71061 (12)	0.60098 (13)	−0.2475 (3)	0.0709 (7)
H3	0.7560	0.6032	−0.2064	0.085*
C4	0.69923 (13)	0.59461 (13)	−0.4180 (3)	0.0743 (7)
H4	0.7370	0.5917	−0.4908	0.089*
C5	0.63235 (13)	0.59259 (12)	−0.4793 (3)	0.0676 (7)
H5	0.6247	0.5889	−0.5938	0.081*
C6	0.57633 (12)	0.59603 (11)	−0.3709 (3)	0.0595 (6)
H6	0.5311	0.5957	−0.4133	0.071*
C7	0.72721 (13)	0.62799 (16)	0.0979 (3)	0.0985 (9)
H7A	0.7570	0.5878	0.0880	0.148*
H7B	0.7223	0.6403	0.2137	0.148*
H7C	0.7475	0.6664	0.0379	0.148*
C8	0.44084 (11)	0.53573 (11)	−0.2157 (3)	0.0621 (6)
H8A	0.4270	0.5660	−0.3056	0.093*
H8B	0.4012	0.5092	−0.1786	0.093*
H8C	0.4767	0.5044	−0.2539	0.093*
C9	0.46824 (11)	0.57866 (10)	−0.0740 (2)	0.0493 (5)
C10	0.42736 (10)	0.59017 (10)	0.0650 (3)	0.0532 (5)
H10	0.3825	0.5715	0.0647	0.064*
C11	0.44829 (11)	0.62827 (10)	0.2084 (3)	0.0535 (5)
C12	0.39786 (11)	0.63783 (11)	0.3497 (3)	0.0548 (6)
C13	0.34395 (11)	0.59189 (12)	0.3815 (3)	0.0654 (6)
H13	0.3387	0.5524	0.3149	0.078*
C14	0.29750 (13)	0.60378 (16)	0.5113 (3)	0.0844 (8)
H14	0.2615	0.5722	0.5320	0.101*
C15	0.30459 (18)	0.66161 (19)	0.6081 (4)	0.0987 (10)
H15	0.2729	0.6702	0.6938	0.118*
C16	0.35791 (18)	0.70697 (16)	0.5801 (4)	0.1039 (10)
H16	0.3628	0.7462	0.6478	0.125*
C17	0.40504 (14)	0.69538 (13)	0.4520 (3)	0.0807 (8)
H17	0.4417	0.7265	0.4348	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0502 (10)	0.1141 (14)	0.0606 (10)	−0.0126 (9)	−0.0072 (8)	0.0100 (9)
O2	0.0586 (10)	0.0757 (11)	0.0757 (10)	−0.0146 (8)	0.0001 (8)	−0.0133 (9)
N1	0.0480 (11)	0.0562 (11)	0.0591 (11)	−0.0065 (9)	−0.0022 (9)	−0.0057 (9)
C1	0.0480 (13)	0.0461 (13)	0.0612 (15)	−0.0023 (10)	−0.0015 (12)	0.0043 (11)
C2	0.0490 (14)	0.0637 (15)	0.0586 (14)	−0.0054 (11)	−0.0027 (11)	0.0112 (12)
C3	0.0492 (14)	0.0939 (19)	0.0696 (17)	−0.0019 (12)	0.0022 (12)	0.0153 (14)
C4	0.0645 (17)	0.0842 (18)	0.0741 (18)	−0.0017 (13)	0.0158 (14)	0.0066 (14)
C5	0.0785 (18)	0.0670 (16)	0.0573 (14)	−0.0099 (13)	0.0032 (14)	0.0044 (12)
C6	0.0564 (14)	0.0610 (15)	0.0612 (15)	−0.0058 (11)	−0.0046 (12)	0.0036 (12)
C7	0.0568 (16)	0.162 (3)	0.0763 (18)	−0.0205 (17)	−0.0157 (14)	0.0046 (18)
C8	0.0584 (14)	0.0648 (14)	0.0633 (14)	−0.0089 (11)	−0.0098 (12)	0.0006 (12)
C9	0.0480 (12)	0.0414 (12)	0.0585 (13)	0.0022 (10)	−0.0109 (11)	0.0047 (10)
C10	0.0415 (12)	0.0545 (13)	0.0637 (14)	0.0003 (10)	−0.0038 (11)	0.0005 (12)
C11	0.0484 (13)	0.0459 (12)	0.0662 (14)	0.0020 (11)	−0.0060 (11)	0.0041 (11)
C12	0.0530 (14)	0.0537 (14)	0.0577 (13)	0.0089 (11)	−0.0037 (11)	0.0026 (11)
C13	0.0589 (15)	0.0682 (16)	0.0690 (15)	0.0030 (12)	0.0007 (13)	0.0041 (13)
C14	0.0638 (17)	0.104 (2)	0.0851 (18)	0.0042 (16)	0.0144 (15)	0.0109 (18)
C15	0.102 (2)	0.106 (3)	0.088 (2)	0.027 (2)	0.0247 (19)	−0.001 (2)
C16	0.132 (3)	0.086 (2)	0.094 (2)	0.007 (2)	0.028 (2)	−0.0225 (18)
C17	0.090 (2)	0.0689 (17)	0.0837 (18)	−0.0053 (14)	0.0130 (16)	−0.0124 (15)

Geometric parameters (Å, º) top

O1—C2	1.368 (2)	C8—C9	1.494 (3)
O1—C7	1.415 (2)	C8—H8A	0.9600
O2—C11	1.256 (2)	C8—H8B	0.9600
N1—C9	1.349 (2)	C8—H8C	0.9600
N1—C1	1.404 (2)	C9—C10	1.377 (3)
N1—H1	0.8600	C10—C11	1.417 (3)
C1—C6	1.384 (3)	C10—H10	0.9300
C1—C2	1.399 (3)	C11—C12	1.497 (3)
C2—C3	1.373 (3)	C12—C17	1.378 (3)
C3—C4	1.387 (3)	C12—C13	1.378 (3)
C3—H3	0.9300	C13—C14	1.385 (3)
C4—C5	1.370 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.357 (4)
C5—C6	1.380 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.357 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—H7A	0.9600	C16—C17	1.383 (3)
C7—H7B	0.9600	C16—H16	0.9300
C7—H7C	0.9600	C17—H17	0.9300

C2—O1—C7	118.28 (17)	C9—C8—H8C	109.5
C9—N1—C1	131.48 (18)	H8A—C8—H8C	109.5
C9—N1—H1	114.3	H8B—C8—H8C	109.5
C1—N1—H1	114.3	N1—C9—C10	119.35 (19)
C6—C1—C2	118.6 (2)	N1—C9—C8	120.57 (19)
C6—C1—N1	125.47 (19)	C10—C9—C8	120.07 (18)
C2—C1—N1	115.77 (19)	C9—C10—C11	125.15 (19)
O1—C2—C3	124.7 (2)	C9—C10—H10	117.4
O1—C2—C1	115.07 (19)	C11—C10—H10	117.4
C3—C2—C1	120.2 (2)	O2—C11—C10	122.6 (2)
C2—C3—C4	120.2 (2)	O2—C11—C12	117.9 (2)
C2—C3—H3	119.9	C10—C11—C12	119.50 (19)
C4—C3—H3	119.9	C17—C12—C13	118.3 (2)
C5—C4—C3	120.1 (2)	C17—C12—C11	118.8 (2)
C5—C4—H4	120.0	C13—C12—C11	122.9 (2)
C3—C4—H4	120.0	C12—C13—C14	120.9 (2)
C4—C5—C6	119.9 (2)	C12—C13—H13	119.6
C4—C5—H5	120.1	C14—C13—H13	119.6
C6—C5—H5	120.1	C15—C14—C13	119.8 (3)
C5—C6—C1	121.0 (2)	C15—C14—H14	120.1
C5—C6—H6	119.5	C13—C14—H14	120.1
C1—C6—H6	119.5	C14—C15—C16	120.1 (3)
O1—C7—H7A	109.5	C14—C15—H15	119.9
O1—C7—H7B	109.5	C16—C15—H15	119.9
H7A—C7—H7B	109.5	C15—C16—C17	120.6 (3)
O1—C7—H7C	109.5	C15—C16—H16	119.7
H7A—C7—H7C	109.5	C17—C16—H16	119.7
H7B—C7—H7C	109.5	C12—C17—C16	120.2 (3)
C9—C8—H8A	109.5	C12—C17—H17	119.9
C9—C8—H8B	109.5	C16—C17—H17	119.9
H8A—C8—H8B	109.5

C9—N1—C1—C6	34.4 (3)	N1—C9—C10—C11	−0.7 (3)
C9—N1—C1—C2	−150.6 (2)	C8—C9—C10—C11	178.21 (18)
C7—O1—C2—C3	8.6 (3)	C9—C10—C11—O2	0.7 (3)
C7—O1—C2—C1	−170.2 (2)	C9—C10—C11—C12	178.91 (18)
C6—C1—C2—O1	175.91 (19)	O2—C11—C12—C17	24.9 (3)
N1—C1—C2—O1	0.5 (3)	C10—C11—C12—C17	−153.5 (2)
C6—C1—C2—C3	−3.0 (3)	O2—C11—C12—C13	−155.7 (2)
N1—C1—C2—C3	−178.40 (19)	C10—C11—C12—C13	25.9 (3)
O1—C2—C3—C4	−178.0 (2)	C17—C12—C13—C14	1.0 (3)
C1—C2—C3—C4	0.8 (4)	C11—C12—C13—C14	−178.4 (2)
C2—C3—C4—C5	1.1 (4)	C12—C13—C14—C15	0.5 (4)
C3—C4—C5—C6	−0.8 (4)	C13—C14—C15—C16	−1.4 (4)
C4—C5—C6—C1	−1.4 (3)	C14—C15—C16—C17	0.8 (5)
C2—C1—C6—C5	3.3 (3)	C13—C12—C17—C16	−1.6 (4)
N1—C1—C6—C5	178.25 (19)	C11—C12—C17—C16	177.8 (2)
C1—N1—C9—C10	177.28 (19)	C15—C16—C17—C12	0.8 (4)
C1—N1—C9—C8	−1.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the benzene ring. C13 is the nearest aromatic atom to H16.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.91	2.639 (2)	139
C3—H3···Cg1ⁱ	0.93	2.79	3.725 (2)	153
C16—H16···π(C13)ⁱⁱ	0.93	2.78	3.688 (4)	167

Symmetry codes: (i) −y+3/2, x, −z−1/2; (ii) −y+1, x+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₂
M_r	267.32
Crystal system, space group	Tetragonal, P4₂/n
Temperature (K)	294
a, c (Å)	19.125 (2), 7.9993 (19)
V (Å³)	2925.9 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.984, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	15499, 3001, 1457
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.115, 1.02
No. of reflections	3001
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.12

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the benzene ring. C13 is the nearest aromatic atom to H16.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.91	2.639 (2)	139.4
C3—H3···Cg1ⁱ	0.93	2.79	3.725 (2)	153
C16—H16···π(C13)ⁱⁱ	0.93	2.78	3.688 (4)	167

Symmetry codes: (i) −y+3/2, x, −z−1/2; (ii) −y+1, x+1/2, z+1/2.

Acknowledgements

This work was supported financially by the Self-Determined Research Program of Jiangnan University.

References

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