(E)-Ethyl 3-(2-fluoro­anilino)-2-(4-methoxy­phen­yl)acrylate

Zheng, Y.; Xiao, Z.-P.; Wang, K.-R.; Zhu, H.-L.

doi:10.1107/S160053680800175X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o489

doi:10.1107/S160053680800175X

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(E)-Ethyl 3-(2-fluoroanilino)-2-(4-methoxyphenyl)acrylate

Yi Zheng,^a Zhu-Ping Xiao,^a Kai-Rui Wang ^a and Hai-Liang Zhu ^a ^*

^aInstitute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hailiang_zhu@163.com

(Received 10 January 2008; accepted 17 January 2008; online 23 January 2008)

The title compound, C₁₈H₁₈FNO₃, consists of three individually planar subunits, namely two substituted benzene rings and one aminoacrylate group. The dihedral angle between the two benzene rings is 47.48 (8)°. The aminoacrylate group forms dihedral angles of 57.95 (7) and 11.27 (6)° with the methoxyphenyl and fluorophenyl rings, respectively.

Related literature

For related literature, see: Xiao et al. (2007 , 2008 ).

Experimental

Crystal data

C₁₈H₁₈FNO₃
M_r = 315.33
Triclinic, $[P \overline 1]$
a = 6.3630 (13) Å
b = 9.4700 (19) Å
c = 13.981 (3) Å
α = 97.68 (3)°
β = 97.38 (3)°
γ = 95.40 (3)°
V = 822.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.40 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.963, T_max = 0.981
3273 measured reflections
2980 independent reflections
1922 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.175
S = 1.09
2980 reflections
209 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.91 (3)	2.65 (3)	3.256 (3)	125 (3)
C12—H12⋯O1ⁱⁱ	0.93	2.53	3.394 (3)	155
N1—H1⋯F1	0.91 (3)	2.26 (3)	2.654 (3)	102 (2)
C13—H13⋯O2	93.0	2.26	2.649 (3)	104
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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/S160053680800175X/pv2066sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800175X/pv2066Isup2.hkl

checkCIF report

Comment top

An enamine, a tautomer of a Schiff base, shows a high similarity to the corresponding Schiff base in chemical structure which shows diverse biological activities. Our recent work affirmed that enamine, like Schiff base, exhibited high antibacterial activity (Xiao et al., 2007; Xiao et al., 2008). We herein report the crystal structure of the title compound, (I), an enamine.

As shown in Fig. 1, (I) is structurally divided into three subunits, and each moiety forms a plane, namely, C1 to C6 forms a plane with the mean deviation of 0.0037 Å, defined as plane I; C7 to C12 forms a plane with the mean deviation of 0.0028 Å, defined as plane II; N1, C13, C14, C15, O1 and O2 is nearly coplanar with the mean deviation of 0.0119 Å, defined as plane III. Plane II and plane III make a dihedral angle with plane I of 47.48 (8) and 11.27 (6) °, and the dihedral angle between plane II and plane III is 57.95 (7) °. The bond distance C13—C14 (1.351 (4) Å) falls in the range of a typical double bond, and C13—N1 bond (1.340 (4) Å) is shorter than the standard C—N single bond (1.48 Å), but longer than a C—N double bond (1.28 Å). This clearly indicates that the p orbital of N1 seems to be conjugated with the π molecular orbital of C13—C14 double bond. All other double bonds and single bonds in the molecule fall in normal range of bond lengths. The structure is stabilized by intramolecular interactions involving rather weak hydrogen bonds of the types N—H···O and C—H···0 as well as intermolecular interactions amino-H···F and C13—H···O2; details of hydrogen-bond geometry are given in Table 1.

Related literature top

For related literature, see: Xiao et al. (2007, 2008).

Experimental top

Equimolar quantities (6 mmol) of ethyl 2-(4-methoxyphenyl)-3- oxopropanoate (1.33 g) and 2-fluorobenzenamine (0.67 g) in absolute alcohol (18 ml) were heated at 344–354 K for 2 h. The excess solvent was removed under reduced pressure. The residue was purified by a flash chromatography with EtOAc-petrolum ether to afford two fractions. The first fraction gave a Z-isomer, and the second fraction, after partial solvent evaporated, furnished colorless blocks of (I) suitable for single-crystal structure determination.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

(E)-Ethyl 3-(2-fluoroanilino)-2-(4-methoxyphenyl)acrylate top

Crystal data top

C₁₈H₁₈FNO₃	Z = 2
M_r = 315.33	F(000) = 332
Triclinic, P1	D_x = 1.273 Mg m⁻³
a = 6.3630 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4700 (19) Å	Cell parameters from 1625 reflections
c = 13.981 (3) Å	θ = 1.5–25.0°
α = 97.68 (3)°	µ = 0.09 mm⁻¹
β = 97.38 (3)°	T = 298 K
γ = 95.40 (3)°	Block, colorless
V = 822.7 (3) Å³	0.40 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2980 independent reflections
Radiation source: fine-focus sealed tube	1922 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω/2θ scans	θ_max = 25.3°, θ_min = 1.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→7
T_min = 0.963, T_max = 0.981	k = −11→11
3273 measured reflections	l = −16→16

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.175	w = 1/[σ²(F_o²) + (0.0677P)² + 0.314P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2980 reflections	Δρ_max = 0.26 e Å⁻³
209 parameters	Δρ_min = −0.21 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: 0.107 (9)

Crystal data top

C₁₈H₁₈FNO₃	γ = 95.40 (3)°
M_r = 315.33	V = 822.7 (3) Å³
Triclinic, P1	Z = 2
a = 6.3630 (13) Å	Mo Kα radiation
b = 9.4700 (19) Å	µ = 0.09 mm⁻¹
c = 13.981 (3) Å	T = 298 K
α = 97.68 (3)°	0.40 × 0.20 × 0.20 mm
β = 97.38 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2980 independent reflections
Absorption correction: ψ scan (North et al., 1968)	1922 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.981	R_int = 0.044
3273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.26 e Å⁻³
2980 reflections	Δρ_min = −0.21 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
O3	0.4465 (3)	0.2358 (2)	0.49646 (15)	0.0698 (6)
O2	−0.0514 (3)	0.6582 (2)	0.10142 (15)	0.0714 (6)
O1	−0.1278 (3)	0.4580 (2)	0.16366 (17)	0.0771 (7)
F1	0.9092 (3)	0.8076 (2)	0.36459 (16)	0.090
C14	0.2001 (4)	0.6001 (3)	0.2237 (2)	0.0519 (7)
C7	0.2661 (4)	0.5043 (3)	0.29442 (19)	0.0490 (6)
C12	0.4551 (4)	0.4418 (3)	0.2923 (2)	0.0555 (7)
H12	0.5395	0.4604	0.2448	0.067*
N1	0.5153 (4)	0.7686 (3)	0.26886 (18)	0.0571 (6)
C9	0.2078 (4)	0.3844 (3)	0.4321 (2)	0.0566 (7)
H9	0.1244	0.3656	0.4799	0.068*
C15	−0.0076 (4)	0.5629 (3)	0.1627 (2)	0.0557 (7)
C1	0.6532 (4)	0.8864 (3)	0.25557 (19)	0.0508 (7)
C10	0.3977 (4)	0.3237 (3)	0.4281 (2)	0.0507 (7)
C8	0.1423 (4)	0.4720 (3)	0.3660 (2)	0.0533 (7)
H8	0.0137	0.5105	0.3689	0.064*
C13	0.3239 (4)	0.7195 (3)	0.2132 (2)	0.0543 (7)
H13	0.2752	0.7717	0.1646	0.065*
C5	1.0048 (5)	1.0171 (3)	0.2990 (3)	0.0709 (9)
H5	1.1400	1.0267	0.3351	0.085*
C11	0.5217 (4)	0.3533 (3)	0.3579 (2)	0.0589 (8)
H11	0.6496	0.3139	0.3549	0.071*
C6	0.8571 (4)	0.9063 (3)	0.3057 (2)	0.0580 (7)
C2	0.6015 (5)	0.9858 (3)	0.1961 (2)	0.0691 (9)
H2	0.4652	0.9776	0.1612	0.083*
C4	0.9513 (5)	1.1144 (3)	0.2383 (2)	0.0738 (9)
H4	1.0502	1.1902	0.2319	0.089*
C3	0.7505 (6)	1.0982 (3)	0.1874 (3)	0.0780 (10)
H3	0.7130	1.1638	0.1461	0.094*
C18	0.6409 (5)	0.1735 (4)	0.4950 (3)	0.0800 (10)
H18A	0.6384	0.1153	0.4330	0.120*
H18B	0.6575	0.1151	0.5459	0.120*
H18C	0.7581	0.2480	0.5050	0.120*
C16	−0.2489 (5)	0.6276 (4)	0.0363 (3)	0.0823 (10)
H16A	−0.3683	0.6266	0.0731	0.099*
H16B	−0.2552	0.5344	−0.0031	0.099*
C17	−0.2589 (7)	0.7410 (5)	−0.0268 (3)	0.1111 (15)
H17A	−0.2568	0.8323	0.0128	0.167*
H17B	−0.3881	0.7218	−0.0724	0.167*
H17C	−0.1384	0.7425	−0.0616	0.167*
H1	0.567 (5)	0.714 (4)	0.313 (3)	0.089 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0550 (12)	0.0796 (14)	0.0784 (14)	0.0045 (10)	0.0128 (10)	0.0239 (12)
O2	0.0526 (12)	0.0798 (15)	0.0765 (14)	−0.0031 (10)	−0.0079 (10)	0.0156 (12)
O1	0.0451 (12)	0.0827 (15)	0.0974 (17)	−0.0184 (11)	0.0068 (11)	0.0121 (12)
F1	0.054	0.096	0.121	−0.007	−0.008	0.048
C14	0.0367 (14)	0.0573 (16)	0.0594 (17)	−0.0039 (12)	0.0121 (12)	0.0024 (13)
C7	0.0382 (14)	0.0497 (15)	0.0562 (16)	−0.0067 (11)	0.0083 (12)	0.0041 (12)
C12	0.0409 (15)	0.0671 (18)	0.0596 (17)	−0.0034 (13)	0.0197 (13)	0.0080 (15)
N1	0.0470 (13)	0.0586 (15)	0.0633 (15)	−0.0110 (11)	−0.0012 (11)	0.0207 (12)
C9	0.0448 (16)	0.0693 (18)	0.0545 (17)	−0.0053 (13)	0.0166 (13)	0.0043 (14)
C15	0.0419 (15)	0.0633 (18)	0.0626 (18)	0.0018 (14)	0.0141 (13)	0.0089 (15)
C1	0.0462 (15)	0.0485 (15)	0.0563 (16)	−0.0034 (12)	0.0086 (12)	0.0084 (13)
C10	0.0418 (15)	0.0516 (15)	0.0560 (16)	−0.0051 (12)	0.0060 (12)	0.0072 (13)
C8	0.0366 (14)	0.0622 (17)	0.0602 (17)	−0.0019 (12)	0.0151 (12)	0.0037 (14)
C13	0.0442 (15)	0.0602 (17)	0.0574 (17)	−0.0025 (13)	0.0080 (13)	0.0098 (13)
C5	0.0482 (17)	0.0658 (19)	0.093 (2)	−0.0126 (15)	0.0047 (16)	0.0110 (18)
C11	0.0365 (14)	0.0654 (18)	0.074 (2)	0.0014 (13)	0.0133 (14)	0.0038 (15)
C6	0.0461 (16)	0.0542 (16)	0.075 (2)	0.0027 (13)	0.0055 (14)	0.0190 (15)
C2	0.0575 (19)	0.068 (2)	0.078 (2)	−0.0089 (15)	−0.0015 (16)	0.0184 (17)
C4	0.070 (2)	0.0584 (19)	0.088 (2)	−0.0192 (16)	0.0142 (18)	0.0082 (17)
C3	0.087 (3)	0.058 (2)	0.088 (2)	−0.0072 (17)	0.004 (2)	0.0278 (18)
C18	0.063 (2)	0.081 (2)	0.097 (3)	0.0125 (17)	0.0042 (18)	0.020 (2)
C16	0.0512 (19)	0.113 (3)	0.074 (2)	0.0140 (18)	−0.0053 (16)	−0.005 (2)
C17	0.112 (3)	0.133 (4)	0.085 (3)	0.041 (3)	−0.017 (2)	0.018 (3)

Geometric parameters (Å, º) top

O3—C10	1.374 (3)	C10—C11	1.376 (4)
O3—C18	1.421 (4)	C8—H8	0.9300
O2—C15	1.349 (3)	C13—H13	0.9300
O2—C16	1.435 (4)	C5—C6	1.363 (4)
O1—C15	1.198 (3)	C5—C4	1.370 (4)
F1—C6	1.362 (3)	C5—H5	0.9300
C14—C13	1.351 (4)	C11—H11	0.9300
C14—C15	1.463 (4)	C2—C3	1.386 (4)
C14—C7	1.478 (4)	C2—H2	0.9300
C7—C12	1.392 (4)	C4—C3	1.365 (5)
C7—C8	1.397 (4)	C4—H4	0.9300
C12—C11	1.377 (4)	C3—H3	0.9300
C12—H12	0.9300	C18—H18A	0.9600
N1—C13	1.364 (3)	C18—H18B	0.9600
N1—C1	1.400 (3)	C18—H18C	0.9600
N1—H1	0.91 (3)	C16—C17	1.479 (5)
C9—C8	1.374 (4)	C16—H16A	0.9700
C9—C10	1.391 (4)	C16—H16B	0.9700
C9—H9	0.9300	C17—H17A	0.9600
C1—C2	1.373 (4)	C17—H17B	0.9600
C1—C6	1.377 (4)	C17—H17C	0.9600

C10—O3—C18	117.1 (2)	C4—C5—H5	120.5
C15—O2—C16	116.8 (3)	C10—C11—C12	119.5 (3)
C13—C14—C15	119.2 (3)	C10—C11—H11	120.2
C13—C14—C7	122.7 (2)	C12—C11—H11	120.2
C15—C14—C7	118.2 (2)	F1—C6—C5	119.7 (3)
C12—C7—C8	117.1 (3)	F1—C6—C1	116.6 (2)
C12—C7—C14	121.1 (2)	C5—C6—C1	123.7 (3)
C8—C7—C14	121.8 (2)	C1—C2—C3	120.7 (3)
C11—C12—C7	122.4 (2)	C1—C2—H2	119.7
C11—C12—H12	118.8	C3—C2—H2	119.7
C7—C12—H12	118.8	C3—C4—C5	118.9 (3)
C13—N1—C1	125.7 (2)	C3—C4—H4	120.6
C13—N1—H1	117 (2)	C5—C4—H4	120.6
C1—N1—H1	116 (2)	C4—C3—C2	121.2 (3)
C8—C9—C10	120.5 (3)	C4—C3—H3	119.4
C8—C9—H9	119.8	C2—C3—H3	119.4
C10—C9—H9	119.8	O3—C18—H18A	109.5
O1—C15—O2	122.0 (3)	O3—C18—H18B	109.5
O1—C15—C14	125.0 (3)	H18A—C18—H18B	109.5
O2—C15—C14	113.0 (2)	O3—C18—H18C	109.5
C2—C1—C6	116.4 (2)	H18A—C18—H18C	109.5
C2—C1—N1	125.1 (3)	H18B—C18—H18C	109.5
C6—C1—N1	118.5 (2)	O2—C16—C17	107.6 (3)
O3—C10—C11	124.7 (3)	O2—C16—H16A	110.2
O3—C10—C9	115.8 (2)	C17—C16—H16A	110.2
C11—C10—C9	119.5 (3)	O2—C16—H16B	110.2
C9—C8—C7	121.0 (3)	C17—C16—H16B	110.2
C9—C8—H8	119.5	H16A—C16—H16B	108.5
C7—C8—H8	119.5	C16—C17—H17A	109.5
C14—C13—N1	124.4 (3)	C16—C17—H17B	109.5
C14—C13—H13	117.8	H17A—C17—H17B	109.5
N1—C13—H13	117.8	C16—C17—H17C	109.5
C6—C5—C4	119.1 (3)	H17A—C17—H17C	109.5
C6—C5—H5	120.5	H17B—C17—H17C	109.5

C13—C14—C7—C12	−56.8 (4)	C14—C7—C8—C9	−179.0 (2)
C15—C14—C7—C12	122.9 (3)	C15—C14—C13—N1	176.7 (3)
C13—C14—C7—C8	123.3 (3)	C7—C14—C13—N1	−3.5 (4)
C15—C14—C7—C8	−57.0 (3)	C1—N1—C13—C14	175.6 (3)
C8—C7—C12—C11	−0.8 (4)	O3—C10—C11—C12	179.2 (2)
C14—C7—C12—C11	179.3 (2)	C9—C10—C11—C12	−0.5 (4)
C16—O2—C15—O1	−0.6 (4)	C7—C12—C11—C10	0.5 (4)
C16—O2—C15—C14	177.9 (2)	C4—C5—C6—F1	179.0 (3)
C13—C14—C15—O1	177.8 (3)	C4—C5—C6—C1	−0.9 (5)
C7—C14—C15—O1	−2.0 (4)	C2—C1—C6—F1	−179.8 (3)
C13—C14—C15—O2	−0.6 (4)	N1—C1—C6—F1	0.4 (4)
C7—C14—C15—O2	179.7 (2)	C2—C1—C6—C5	0.1 (5)
C13—N1—C1—C2	12.3 (5)	N1—C1—C6—C5	−179.7 (3)
C13—N1—C1—C6	−168.0 (3)	C6—C1—C2—C3	0.7 (5)
C18—O3—C10—C11	1.1 (4)	N1—C1—C2—C3	−179.5 (3)
C18—O3—C10—C9	−179.3 (3)	C6—C5—C4—C3	0.9 (5)
C8—C9—C10—O3	−178.9 (2)	C5—C4—C3—C2	−0.1 (5)
C8—C9—C10—C11	0.8 (4)	C1—C2—C3—C4	−0.8 (5)
C10—C9—C8—C7	−1.1 (4)	C15—O2—C16—C17	−177.3 (3)
C12—C7—C8—C9	1.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.91 (3)	2.65 (3)	3.256 (3)	125 (3)
C12—H12···O1ⁱⁱ	0.93	2.53	3.394 (3)	155
N1—H1···F1	0.91 (3)	2.26 (3)	2.654 (3)	102 (2)
C13—H13···O2	93.0	2.26	2.649 (3)	104

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈FNO₃
M_r	315.33
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.3630 (13), 9.4700 (19), 13.981 (3)
α, β, γ (°)	97.68 (3), 97.38 (3), 95.40 (3)
V (Å³)	822.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.963, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	3273, 2980, 1922
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.175, 1.09
No. of reflections	2980
No. of parameters	209
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.21

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.91 (3)	2.65 (3)	3.256 (3)	125 (3)
C12—H12···O1ⁱⁱ	0.93	2.53	3.394 (3)	155
N1—H1···F1	0.91 (3)	2.26 (3)	2.654 (3)	102 (2)
C13—H13···O2	93.0	2.26	2.649 (3)	104

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

Acknowledgements

This work was financed by the National Natural Science Foundation of China (grant No. 30772627).

References

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