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

Zheng, D.-G.; Xiao, Z.-P.

doi:10.1107/S1600536808039184

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2456

doi:10.1107/S1600536808039184

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

Da-Gui Zheng ^a ^* and Zhu-Ping Xiao ^b

^aKey Laboratory of Applied Organic Chemistry, Higher Institutions of Jiangxi Province, Shangrao Normal College, Shangrao 334001, Jiangxi, People's Republic of China, and ^bCollege of Chemistry & Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
^*Correspondence e-mail: shenyangzhou@163.com

(Received 21 October 2008; accepted 21 November 2008; online 26 November 2008)

In the title compound, C₁₈H₁₈FNO₃, the dihedral angles between the two benzene rings and the plane through the acrylate group and the fluorophenyl ring are 61.58 (8) and 13.33 (9)°, respectively. Molecules are linked into ribbons through C—H⋯O and N—H⋯O hydrogen bonds, and further linked by C—H⋯π interactions, forming a three-dimensional network.

Related literature

For related literature regarding the antimicrobial activity of 3-arylamino-2-aryl acrylates, see: Shi et al. (2007 ); Xiao et al. (2007 , 2008 ); Xue et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₈FNO₃
M_r = 315.33
Monoclinic, P 2₁ /c
a = 19.000 (4) Å
b = 6.0400 (12) Å
c = 15.081 (3) Å
β = 109.64 (3)°
V = 1630.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.972, T_max = 0.981
3073 measured reflections
2943 independent reflections
1807 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.162
S = 1.02
2943 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.49	3.401 (3)	167
N1—H1⋯O3ⁱⁱ	0.83 (2)	2.56 (3)	3.229 (3)	138 (2)
C16—H16B⋯Cg1ⁱⁱⁱ	0.97	2.99	3.788 (3)	141
C18—H18A⋯Cg2^iv	0.96	2.80	3.626 (3)	145
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+1, -y, -z. Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039184/ez2149sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039184/ez2149Isup2.hkl

checkCIF report

Comment top

3-Arylamino-2-aryl acrylates, enamines structurally like Schiff bases, show high antimicrobial activity (Xiao et al., 2007; Xue et al., 2007; Xiao et al., 2008; Shi et al. 2007), especially for bacteria. In a continuation of our work on the structural characterization of enamine derivatives, we report here the crystal structure of the title compound, (I) (Fig. 1).

The N1—H group lies approximately in the same planes as the fluorophenyl and acrylate groups (with dihedral angles of 4.7 (2) ° and 8.9 (2) °, respectively), suggesting that one of the p orbitals of N1 is conjugated with the π molecular orbitals of the two moieties, thus shortening both the C1—N1 (1.408 (3) Å) and C13—N1 (1.359 (3) Å) bonds. All other double and single bond lengths fall within normal values (Allen et al., 1987).

Molecules are linked into ribbons running along the b-axis via C—H···O and N—H···O hydrogen bonds (Fig. 2 and Table 1). These ribbons are interconnected via weak C16-H16B···π (centroid of C1 to C6) and C18-H18A···π (centroid of C7 to C12) interactions (Table 1 and Fig. 3).

Related literature top

For related literature regarding the antimicrobial activity of 3-arylamino-2-aryl acrylates, see: Shi et al. (2007); Xiao et al. (2007, 2008); Xue et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

Equimolar quantities (6 mmol) of ethyl 2-(4-methoxyphenyl)-3- oxopropanoate (1.33 g) and 4-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 flash chromatography with EtOAc-petrolum ether (1:10) to afford two fractions. The first fraction gave the Z-isomer, and the second fraction, after partial solvent evaporation, 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: SHELXP97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of the title compound showing the ribbons connected by C—H···O and N—H···O hydrogen bonds (indicated by dashed lines), viewed along the b axis.
	Fig. 3. The crystal packing of the title compound, showing the linking of the hydrogen bonded ribbons by C—H···π interactions. Dashed lines indicate C—H···O, N—H···O and C-H···π interactions.

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

Crystal data top

C₁₈H₁₈FNO₃	F(000) = 664
M_r = 315.33	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.000 (4) Å	Cell parameters from 1632 reflections
b = 6.0400 (12) Å	θ = 1.4–24.7°
c = 15.081 (3) Å	µ = 0.10 mm⁻¹
β = 109.64 (3)°	T = 293 K
V = 1630.0 (6) Å³	Block, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2943 independent reflections
Radiation source: fine-focus sealed tube	1807 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω/2θ scans	θ_max = 25.3°, θ_min = 1.1°
Absorption correction: ψ scan (North et al., 1968)	h = −22→21
T_min = 0.972, T_max = 0.981	k = −7→0
3073 measured reflections	l = 0→18

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.0863P)² + 0.0162P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2943 reflections	Δρ_max = 0.15 e Å⁻³
215 parameters	Δρ_min = −0.16 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: 0.044 (4)

Crystal data top

C₁₈H₁₈FNO₃	V = 1630.0 (6) Å³
M_r = 315.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.000 (4) Å	µ = 0.10 mm⁻¹
b = 6.0400 (12) Å	T = 293 K
c = 15.081 (3) Å	0.30 × 0.30 × 0.20 mm
β = 109.64 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2943 independent reflections
Absorption correction: ψ scan (North et al., 1968)	1807 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.981	R_int = 0.026
3073 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.15 e Å⁻³
2943 reflections	Δρ_min = −0.16 e Å⁻³
215 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
C1	0.78366 (12)	0.7249 (4)	0.02705 (17)	0.0468 (6)
C2	0.86057 (14)	0.7171 (5)	0.0575 (2)	0.0637 (8)
H2	0.8858	0.6095	0.1005	0.076*
C3	0.90034 (15)	0.8673 (6)	0.0246 (2)	0.0733 (9)
H3	0.9523	0.8617	0.0451	0.088*
C4	0.86292 (16)	1.0237 (5)	−0.0380 (2)	0.0682 (9)
C5	0.78687 (17)	1.0339 (5)	−0.0708 (2)	0.0721 (9)
H5	0.7620	1.1403	−0.1148	0.086*
C6	0.74779 (15)	0.8829 (5)	−0.0373 (2)	0.0640 (8)
H6	0.6958	0.8882	−0.0588	0.077*
C7	0.64691 (12)	0.3267 (4)	0.14607 (16)	0.0431 (6)
C8	0.59236 (13)	0.1688 (4)	0.10497 (18)	0.0494 (7)
H8	0.6063	0.0338	0.0862	0.059*
C9	0.51803 (13)	0.2090 (5)	0.09161 (18)	0.0513 (7)
H9	0.4825	0.1013	0.0639	0.062*
C10	0.49607 (13)	0.4075 (4)	0.11902 (17)	0.0470 (6)
C11	0.54911 (13)	0.5661 (4)	0.16114 (19)	0.0523 (7)
H11	0.5350	0.7002	0.1804	0.063*
C12	0.62356 (13)	0.5233 (4)	0.17434 (19)	0.0510 (7)
H12	0.6591	0.6302	0.2032	0.061*
C13	0.76733 (13)	0.4059 (4)	0.12087 (17)	0.0465 (6)
H13	0.8176	0.3699	0.1356	0.056*
C14	0.72695 (12)	0.2824 (4)	0.16064 (16)	0.0433 (6)
C15	0.76226 (13)	0.0959 (4)	0.22121 (18)	0.0458 (6)
C16	0.87264 (15)	−0.1081 (5)	0.2948 (2)	0.0669 (8)
H16A	0.8550	−0.2514	0.2671	0.080*
H16B	0.8630	−0.0960	0.3538	0.080*
C17	0.95460 (15)	−0.0844 (6)	0.3113 (3)	0.0887 (11)
H17A	0.9637	−0.1045	0.2530	0.133*
H17B	0.9817	−0.1941	0.3558	0.133*
H17C	0.9709	0.0606	0.3358	0.133*
C18	0.39590 (15)	0.6241 (5)	0.1368 (2)	0.0751 (9)
H18A	0.4220	0.6374	0.2032	0.113*
H18B	0.3432	0.6130	0.1255	0.113*
H18C	0.4057	0.7521	0.1051	0.113*
F1	0.90279 (11)	1.1721 (4)	−0.07006 (17)	0.1125 (8)
H1	0.6954 (14)	0.606 (4)	0.0454 (19)	0.059 (8)*
N1	0.74101 (12)	0.5785 (4)	0.06106 (16)	0.0567 (6)
O1	0.73060 (10)	−0.0227 (3)	0.26022 (14)	0.0667 (6)
O2	0.83483 (9)	0.0669 (3)	0.23152 (13)	0.0584 (5)
O3	0.42082 (9)	0.4306 (3)	0.10206 (13)	0.0618 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0401 (13)	0.0536 (15)	0.0482 (14)	−0.0053 (12)	0.0170 (11)	0.0019 (13)
C2	0.0465 (15)	0.076 (2)	0.0642 (17)	−0.0017 (15)	0.0135 (13)	0.0221 (16)
C3	0.0434 (15)	0.093 (2)	0.082 (2)	−0.0056 (16)	0.0193 (15)	0.026 (2)
C4	0.0596 (18)	0.073 (2)	0.082 (2)	−0.0085 (16)	0.0371 (16)	0.0172 (18)
C5	0.074 (2)	0.065 (2)	0.085 (2)	0.0109 (16)	0.0370 (17)	0.0304 (18)
C6	0.0450 (15)	0.0681 (19)	0.078 (2)	0.0063 (14)	0.0193 (14)	0.0157 (17)
C7	0.0403 (13)	0.0433 (14)	0.0443 (14)	−0.0067 (11)	0.0125 (10)	0.0005 (12)
C8	0.0456 (14)	0.0464 (15)	0.0548 (15)	−0.0018 (12)	0.0150 (12)	−0.0075 (13)
C9	0.0412 (13)	0.0540 (17)	0.0528 (15)	−0.0131 (12)	0.0081 (11)	−0.0127 (13)
C10	0.0361 (12)	0.0550 (16)	0.0482 (14)	−0.0008 (12)	0.0118 (11)	0.0038 (13)
C11	0.0490 (15)	0.0417 (14)	0.0668 (17)	−0.0045 (12)	0.0202 (13)	−0.0085 (13)
C12	0.0449 (14)	0.0364 (14)	0.0694 (18)	−0.0074 (11)	0.0164 (13)	−0.0033 (13)
C13	0.0364 (12)	0.0493 (15)	0.0502 (15)	−0.0021 (12)	0.0097 (11)	0.0004 (13)
C14	0.0410 (13)	0.0406 (14)	0.0471 (14)	−0.0060 (11)	0.0133 (11)	−0.0046 (12)
C15	0.0441 (13)	0.0422 (14)	0.0521 (15)	−0.0065 (12)	0.0174 (12)	−0.0088 (13)
C16	0.0616 (17)	0.0523 (17)	0.076 (2)	0.0087 (15)	0.0087 (15)	0.0069 (16)
C17	0.0565 (18)	0.093 (3)	0.104 (3)	0.0198 (18)	0.0101 (18)	0.004 (2)
C18	0.0521 (16)	0.091 (2)	0.085 (2)	0.0079 (16)	0.0267 (16)	−0.0201 (19)
F1	0.0896 (13)	0.1078 (17)	0.154 (2)	−0.0112 (12)	0.0592 (14)	0.0556 (15)
N1	0.0359 (12)	0.0658 (15)	0.0665 (15)	0.0010 (12)	0.0146 (11)	0.0177 (13)
O1	0.0589 (11)	0.0540 (12)	0.0889 (15)	−0.0014 (10)	0.0272 (11)	0.0181 (11)
O2	0.0439 (10)	0.0583 (12)	0.0718 (13)	0.0047 (9)	0.0177 (9)	0.0084 (10)
O3	0.0399 (10)	0.0733 (13)	0.0714 (13)	0.0012 (9)	0.0177 (9)	−0.0061 (11)

Geometric parameters (Å, º) top

C1—C6	1.368 (4)	C11—C12	1.385 (3)
C1—C2	1.377 (3)	C11—H11	0.9300
C1—N1	1.408 (3)	C12—H12	0.9300
C2—C3	1.375 (4)	C13—C14	1.347 (3)
C2—H2	0.9300	C13—N1	1.359 (3)
C3—C4	1.355 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.463 (3)
C4—C5	1.362 (4)	C15—O1	1.208 (3)
C4—F1	1.363 (3)	C15—O2	1.346 (3)
C5—C6	1.375 (4)	C16—O2	1.444 (3)
C5—H5	0.9300	C16—C17	1.499 (4)
C6—H6	0.9300	C16—H16A	0.9700
C7—C12	1.384 (3)	C16—H16B	0.9700
C7—C8	1.392 (3)	C17—H17A	0.9600
C7—C14	1.486 (3)	C17—H17B	0.9600
C8—C9	1.379 (3)	C17—H17C	0.9600
C8—H8	0.9300	C18—O3	1.425 (3)
C9—C10	1.378 (4)	C18—H18A	0.9600
C9—H9	0.9300	C18—H18B	0.9600
C10—O3	1.372 (3)	C18—H18C	0.9600
C10—C11	1.381 (3)	N1—H1	0.83 (2)

C6—C1—C2	118.7 (2)	C7—C12—H12	118.9
C6—C1—N1	119.1 (2)	C11—C12—H12	118.9
C2—C1—N1	122.2 (2)	C14—C13—N1	125.6 (2)
C3—C2—C1	120.5 (3)	C14—C13—H13	117.2
C3—C2—H2	119.8	N1—C13—H13	117.2
C1—C2—H2	119.8	C13—C14—C15	119.6 (2)
C4—C3—C2	119.2 (2)	C13—C14—C7	122.8 (2)
C4—C3—H3	120.4	C15—C14—C7	117.6 (2)
C2—C3—H3	120.4	O1—C15—O2	121.7 (2)
C3—C4—C5	121.9 (3)	O1—C15—C14	124.2 (2)
C3—C4—F1	118.8 (3)	O2—C15—C14	114.2 (2)
C5—C4—F1	119.3 (3)	O2—C16—C17	107.4 (2)
C4—C5—C6	118.3 (3)	O2—C16—H16A	110.2
C4—C5—H5	120.8	C17—C16—H16A	110.2
C6—C5—H5	120.8	O2—C16—H16B	110.2
C1—C6—C5	121.4 (2)	C17—C16—H16B	110.2
C1—C6—H6	119.3	H16A—C16—H16B	108.5
C5—C6—H6	119.3	C16—C17—H17A	109.5
C12—C7—C8	117.2 (2)	C16—C17—H17B	109.5
C12—C7—C14	121.8 (2)	H17A—C17—H17B	109.5
C8—C7—C14	120.9 (2)	C16—C17—H17C	109.5
C9—C8—C7	121.1 (2)	H17A—C17—H17C	109.5
C9—C8—H8	119.4	H17B—C17—H17C	109.5
C7—C8—H8	119.4	O3—C18—H18A	109.5
C10—C9—C8	120.5 (2)	O3—C18—H18B	109.5
C10—C9—H9	119.7	H18A—C18—H18B	109.5
C8—C9—H9	119.7	O3—C18—H18C	109.5
O3—C10—C9	115.8 (2)	H18A—C18—H18C	109.5
O3—C10—C11	124.6 (2)	H18B—C18—H18C	109.5
C9—C10—C11	119.6 (2)	C13—N1—C1	126.5 (2)
C10—C11—C12	119.2 (2)	C13—N1—H1	117.1 (19)
C10—C11—H11	120.4	C1—N1—H1	116.3 (19)
C12—C11—H11	120.4	C15—O2—C16	115.8 (2)
C7—C12—C11	122.3 (2)	C10—O3—C18	118.0 (2)

C6—C1—C2—C3	0.9 (4)	C10—C11—C12—C7	0.5 (4)
N1—C1—C2—C3	−178.1 (3)	N1—C13—C14—C15	177.8 (2)
C1—C2—C3—C4	0.1 (5)	N1—C13—C14—C7	−2.3 (4)
C2—C3—C4—C5	−1.3 (5)	C12—C7—C14—C13	−62.1 (3)
C2—C3—C4—F1	179.9 (3)	C8—C7—C14—C13	119.3 (3)
C3—C4—C5—C6	1.4 (5)	C12—C7—C14—C15	117.8 (3)
F1—C4—C5—C6	−179.8 (3)	C8—C7—C14—C15	−60.8 (3)
C2—C1—C6—C5	−0.8 (4)	C13—C14—C15—O1	179.5 (2)
N1—C1—C6—C5	178.2 (3)	C7—C14—C15—O1	−0.4 (4)
C4—C5—C6—C1	−0.3 (5)	C13—C14—C15—O2	0.3 (3)
C12—C7—C8—C9	1.2 (4)	C7—C14—C15—O2	−179.6 (2)
C14—C7—C8—C9	179.8 (2)	C14—C13—N1—C1	172.4 (2)
C7—C8—C9—C10	−0.1 (4)	C6—C1—N1—C13	176.2 (3)
C8—C9—C10—O3	179.7 (2)	C2—C1—N1—C13	−4.8 (4)
C8—C9—C10—C11	−0.7 (4)	O1—C15—O2—C16	−2.4 (3)
O3—C10—C11—C12	−179.9 (2)	C14—C15—O2—C16	176.8 (2)
C9—C10—C11—C12	0.5 (4)	C17—C16—O2—C15	−169.0 (2)
C8—C7—C12—C11	−1.3 (4)	C9—C10—O3—C18	174.3 (2)
C14—C7—C12—C11	−180.0 (2)	C11—C10—O3—C18	−5.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.49	3.401 (3)	167
N1—H1···O3ⁱⁱ	0.83 (2)	2.56 (3)	3.229 (3)	138 (2)
C16—H16B···Cg1ⁱⁱⁱ	0.97	2.99	3.788 (3)	141
C18—H18A···Cg2^iv	0.96	2.80	3.626 (3)	145

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈FNO₃
M_r	315.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	19.000 (4), 6.0400 (12), 15.081 (3)
β (°)	109.64 (3)
V (Å³)	1630.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.972, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	3073, 2943, 1807
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.162, 1.02
No. of reflections	2943
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXP97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.49	3.401 (3)	166.6
N1—H1···O3ⁱⁱ	0.83 (2)	2.56 (3)	3.229 (3)	138 (2)
C16—H16B···Cg1ⁱⁱⁱ	0.97	2.99	3.788 (3)	141
C18—H18A···Cg2^iv	0.96	2.80	3.626 (3)	145

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

Acknowledgements

This research was financially supported by the Education Department of Jiangxi Province, P. R. China (grant No. 2007–402).

References

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