5-Benzyl-7-methyl­hexa­hydro-3a,7-methano-1H-furo[3,4-c]azocine-3,10(4H)-dione

Yang, Z.-K.; Wang, F.-P.

doi:10.1107/S160053681100300X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o577

doi:10.1107/S160053681100300X

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5-Benzyl-7-methylhexahydro-3a,7-methano-1H-furo[3,4-c]azocine-3,10(4H)-dione

Zhan-Kun Yang ^a and Feng-Peng Wang ^a ^*

^aDepartment of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: wfp@scu.edu.cn

(Received 9 January 2011; accepted 22 January 2011; online 5 February 2011)

The title compound, C₁₈H₂₁NO₃, was obtained via a double Mannich condensation reaction of 6-methyltetrahydroisobenzofuran-1,7(3H,7aH)-dione with formaldehyde and benzylamine. The molecule contains three fused rings of which the cyclohexanone and piperidine rings adopt chair conformations and the furanone ring assumes an envelope conformation. An intermolecular C—H⋯π interaction is present in the crystal structure.

Related literature

For the double Mannich condensation reaction, see: Guthmann et al. (2009 ); Coates et al. (1994 ); Barker et al. (2002 ). For the methylation of the β-keto ester in the synthesis of the title compound, see: Weiler (1970 ).

Experimental

Crystal data

C₁₈H₂₁NO₃
M_r = 299.36
Orthorhombic, P n a 2₁
a = 10.795 (2) Å
b = 14.386 (3) Å
c = 9.797 (2) Å
V = 1521.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn 724 diffractometer
10268 measured reflections
1584 independent reflections
1546 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.167
S = 1.16
1584 reflections
200 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cgⁱ	0.97	2.87	3.833 (6)	169
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100300X/xu5143sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100300X/xu5143Isup2.hkl

checkCIF report

Comment top

The AE rings of diterpenoid alkaloids have received much attention as key intermediate in the total syntheses of diterpenoid alkaloids. Double Mannich condensation (Guthmann et al., 2009; Coates et al., 1994; Barker et al., 2002) is an efficient method to append the E ring to the A ring. Therefore, we have designed and synthesized the racemic 1-substituted AE-bicyclic analogue by double Mannich condensation. Herein, we report the structure of the title compound.

As illustrated in Fig. 1, the molecule of the title compound is constructed from the fusion of a cyclohexanone ring, a piperidine ring and a furanone ring. The two six-membered rings are in standard chair conformations. The furanone ring is cis-fused with the cyclohexanone ring and adopts envelope conformation. The bond angles around C4 and C5 are indicative of sp² hybridization for the two atoms. And the strain in the furanone ring is illustrated by the much distorted triangular geometry of C4 atom and the bond angles around C4 range between 109.7 (4) and 128.6 (5)°.

Related literature top

For the double Mannich condensation reaction, see: Guthmann et al. (2009); Coates et al. (1994); Barker et al. (2002). For the methylation of β-keto ester in the synthesis of the title compound, see: Weiler (1970).

Experimental top

The intermediate, 6-methyltetrahydroisobenzofuran-1,7(3H,7aH)-dione (1b), was synthesized according to the procedure described by Weiler (1970). A solution of tetrahydroisobenzofuran-1,7(3H,7aH)-dione (1.00 g, 6.49 mmol) in THF (10 mL) was added to 1M lithium diisopropylamide solution in THF (14.2 ml, 14.2 mmol) at 273 K. After 30 min, CH₃I (0.48 ml, 7.71 mmol) was added dropwise in the mixture. Then the mixture was stirred at the same temperature for 2 h. H₂O (20 mL) was added and the solution was extracted with CH₂Cl₂ (60 mL). The organic layer was dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate/hexane, v:v, 1:2) to give 1b. (0.382 g, yield 35%) as a colourless oil.

To a solution of 1b (200 mg, 1.19 mmol) in EtOH (300 mL) was added 37% CH₂O solution (0.29 mL, 3.57 mmol) and phenylmethanamine (195 µL, 1.79 mmol). The reaction mixture was refluxing for 48 h and then concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate/hexane, v:v, 1:4) to give the title compound (107 mg, yield 30%) as a white solid. Crystallization from a ethyl acetate-petroleum ether system yielded colourless crystals suitable for single-crystal structure determination.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); 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 with displacement ellipsoids at 30% probability level.

5-Benzyl-7-methylhexahydro-3a,7-methano-1H-furo[3,4-c]azocine- 3,10(4H)-dione top

Crystal data top

C₁₈H₂₁NO₃	F(000) = 640
M_r = 299.36	D_x = 1.307 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3565 reflections
a = 10.795 (2) Å	θ = 2.5–27.5°
b = 14.386 (3) Å	µ = 0.09 mm⁻¹
c = 9.797 (2) Å	T = 293 K
V = 1521.5 (5) Å³	Prism, colourless
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku Saturn 724 diffractometer	1546 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 26.0°, θ_min = 2.5°
ω scans	h = −12→13
10268 measured reflections	k = −17→17
1584 independent reflections	l = −10→12

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)] = 0.067	H-atom parameters constrained
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.0752P)² + 0.8271P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max < 0.001
1584 reflections	Δρ_max = 0.15 e Å⁻³
200 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Absolute structure: unk
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₈H₂₁NO₃	V = 1521.5 (5) Å³
M_r = 299.36	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 10.795 (2) Å	µ = 0.09 mm⁻¹
b = 14.386 (3) Å	T = 293 K
c = 9.797 (2) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku Saturn 724 diffractometer	1546 reflections with I > 2σ(I)
10268 measured reflections	R_int = 0.045
1584 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	1 restraint
wR(F²) = 0.167	H-atom parameters constrained
S = 1.16	Δρ_max = 0.15 e Å⁻³
1584 reflections	Δρ_min = −0.16 e Å⁻³
200 parameters	Absolute structure: unk

Special details top

Experimental. For 6-methyltetrahydroisobenzofuran-1,7(3H, 7aH)-dione (1b), ¹H NMR (400 MHz, CDCl₃): δ 4.28 (dd, J = 9.2, 4.8 Hz, 1H), 4.15 (d, J = 9.2 Hz, 1H), 3.46(d, J = 7.2 Hz,1H), 2.97–2.91 (m, 1H), 2.40–2.34 (m, 1H), 2.07–2.03 (m, 2H), 1.79–1.69 (m, 1H), 1.49–1.40 (m, 1H), 1.09(d, J = 6.0 Hz, 3H); ¹³C NMR (100 MHz CDCl₃): δ 204.3, 172.2, 72.1, 54.4, 44.0, 40.7, 32.5, 26.9, 14.2.

For 5-benzyl-7-methylhexahydro-1H-3a,7-methanofuro [3,4-c]azocine- 3,10(4H)-dione (1), ¹H NMR (400 MHz, CDCl₃): δ 7.37–7.27(m, 5H), 4.29 (t, J = 9.2 Hz, 1H), 3.83 (dd, J =9.2, 10.4 Hz, 1H), 3.61, 3.51 (ABq, J = 13.0 Hz, 2H), 3.14–3.12(m, 1H), 3.07, 2.85 (ABq, J = 11.2 Hz, 2H), 3.05, 2.38 (ABx, J = 2.4, 12.0 Hz, 2H), 2.81–2.75 (m, 1H), 2.26–2.20 (m, 1H), 1.92–1.87 (m, 1H), 1.44–1.38 (m, 1H), 0.99 (s, 3H); ¹³C NMR (100 MHz, CDC_l3): δ 210.7, 173.4, 137.7, 128.7, 128.5, 127.5, 69.2, 65.8, 61.5, 59.8, 58.6, 47.5, 46.1, 39.2, 22.0, 20.7

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	0.4992 (4)	1.0732 (2)	0.3736 (5)	0.0579 (10)
O2	0.6479 (3)	0.9870 (3)	0.2802 (5)	0.0630 (11)
O3	0.5495 (4)	0.8809 (3)	0.5463 (4)	0.0635 (11)
N1	0.3480 (3)	0.7803 (3)	0.2454 (4)	0.0389 (9)
C1	0.3691 (5)	1.0624 (4)	0.4104 (7)	0.0556 (14)
H1B	0.3216	1.1164	0.3825	0.067*
H1A	0.3601	1.0542	0.5082	0.067*
C2	0.3259 (4)	0.9760 (3)	0.3343 (5)	0.0424 (11)
H2	0.3083	0.9938	0.2398	0.051*
C3	0.4465 (4)	0.9178 (3)	0.3349 (5)	0.0346 (10)
C4	0.5441 (5)	0.9930 (4)	0.3236 (5)	0.0443 (11)
C5	0.4612 (4)	0.8689 (3)	0.4713 (5)	0.0371 (11)
C6	0.3570 (4)	0.8020 (3)	0.4992 (5)	0.0405 (11)
C7	0.2386 (4)	0.8628 (4)	0.5110 (6)	0.0483 (12)
H7A	0.1679	0.8219	0.5225	0.058*
H7B	0.2452	0.9004	0.5929	0.058*
C8	0.2129 (4)	0.9273 (4)	0.3903 (6)	0.0465 (12)
H8A	0.1754	0.8912	0.3176	0.056*
H8B	0.1532	0.9739	0.4186	0.056*
C9	0.3758 (6)	0.7484 (4)	0.6313 (6)	0.0606 (15)
H9B	0.4532	0.7157	0.6276	0.091*
H9A	0.3094	0.7046	0.6428	0.091*
H9C	0.3765	0.7909	0.7068	0.091*
C10	0.3545 (5)	0.7331 (3)	0.3766 (6)	0.0442 (11)
H10B	0.4286	0.6950	0.3792	0.053*
H10A	0.2835	0.6923	0.3858	0.053*
C11	0.4512 (4)	0.8433 (3)	0.2246 (5)	0.0401 (11)
H11B	0.4455	0.8718	0.1350	0.048*
H11A	0.5289	0.8096	0.2300	0.048*
C12	0.3250 (5)	0.7190 (4)	0.1294 (6)	0.0476 (12)
H12B	0.3046	0.7575	0.0513	0.057*
H12A	0.2523	0.6819	0.1500	0.057*
C13	0.4275 (4)	0.6538 (3)	0.0878 (5)	0.0386 (11)
C14	0.5080 (6)	0.6763 (4)	−0.0179 (6)	0.0583 (15)
H14	0.4984	0.7322	−0.0644	0.070*
C15	0.6027 (6)	0.6160 (5)	−0.0545 (7)	0.0690 (19)
H15	0.6555	0.6315	−0.1260	0.083*
C16	0.6189 (6)	0.5334 (5)	0.0141 (7)	0.0663 (18)
H16	0.6829	0.4934	−0.0098	0.080*
C17	0.5400 (6)	0.5112 (4)	0.1175 (7)	0.0635 (17)
H17	0.5504	0.4554	0.1641	0.076*
C18	0.4448 (5)	0.5703 (3)	0.1542 (6)	0.0470 (12)
H18	0.3916	0.5535	0.2246	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.071 (2)	0.0449 (19)	0.058 (2)	−0.0122 (18)	0.002 (2)	−0.005 (2)
O2	0.045 (2)	0.072 (3)	0.072 (3)	−0.0190 (19)	0.010 (2)	−0.007 (2)
O3	0.052 (2)	0.083 (3)	0.056 (3)	−0.010 (2)	−0.0164 (19)	0.003 (2)
N1	0.038 (2)	0.040 (2)	0.039 (2)	0.0011 (17)	−0.0009 (17)	−0.0094 (17)
C1	0.059 (3)	0.043 (3)	0.065 (4)	0.010 (2)	0.010 (3)	−0.006 (3)
C2	0.041 (2)	0.045 (3)	0.042 (3)	0.011 (2)	−0.004 (2)	−0.001 (2)
C3	0.032 (2)	0.035 (2)	0.037 (2)	−0.0028 (18)	0.0027 (18)	−0.0030 (18)
C4	0.053 (3)	0.044 (3)	0.037 (3)	−0.007 (2)	−0.007 (2)	−0.005 (2)
C5	0.031 (2)	0.043 (2)	0.038 (3)	0.0065 (19)	−0.0019 (19)	−0.009 (2)
C6	0.044 (2)	0.038 (2)	0.040 (3)	−0.002 (2)	0.002 (2)	0.001 (2)
C7	0.038 (2)	0.055 (3)	0.052 (3)	0.000 (2)	0.010 (2)	−0.009 (3)
C8	0.034 (2)	0.056 (3)	0.050 (3)	0.015 (2)	0.002 (2)	−0.005 (3)
C9	0.077 (4)	0.059 (3)	0.045 (3)	0.002 (3)	0.003 (3)	0.007 (3)
C10	0.044 (2)	0.037 (2)	0.052 (3)	−0.004 (2)	0.002 (2)	−0.012 (2)
C11	0.042 (2)	0.038 (2)	0.040 (3)	0.000 (2)	0.000 (2)	−0.005 (2)
C12	0.040 (2)	0.053 (3)	0.050 (3)	−0.001 (2)	−0.007 (2)	−0.013 (2)
C13	0.037 (2)	0.040 (2)	0.039 (3)	−0.009 (2)	−0.006 (2)	−0.013 (2)
C14	0.075 (4)	0.055 (3)	0.045 (3)	−0.012 (3)	0.010 (3)	−0.011 (3)
C15	0.058 (3)	0.084 (5)	0.065 (4)	−0.018 (3)	0.021 (3)	−0.033 (4)
C16	0.052 (3)	0.078 (4)	0.068 (4)	0.012 (3)	−0.004 (3)	−0.041 (4)
C17	0.069 (4)	0.051 (3)	0.070 (4)	0.014 (3)	−0.022 (4)	−0.022 (3)
C18	0.055 (3)	0.042 (3)	0.044 (3)	−0.004 (2)	−0.001 (2)	−0.010 (2)

Geometric parameters (Å, º) top

O1—C1	1.458 (7)	C8—H8A	0.9700
O1—C4	1.344 (6)	C8—H8B	0.9700
O2—C4	1.202 (6)	C9—H9B	0.9600
O3—C5	1.216 (6)	C9—H9A	0.9600
N1—C10	1.455 (7)	C9—H9C	0.9600
N1—C11	1.451 (6)	C10—H10B	0.9700
N1—C12	1.460 (6)	C10—H10A	0.9700
C1—H1B	0.9700	C11—H11B	0.9700
C1—H1A	0.9700	C11—H11A	0.9700
C1—C2	1.523 (7)	C12—H12B	0.9700
C2—H2	0.9800	C12—H12A	0.9700
C2—C3	1.548 (6)	C12—C13	1.507 (7)
C2—C8	1.509 (7)	C13—C14	1.389 (8)
C3—C4	1.513 (7)	C13—C18	1.380 (7)
C3—C5	1.519 (7)	C14—H14	0.9300
C3—C11	1.523 (6)	C14—C15	1.388 (9)
C5—C6	1.505 (7)	C15—H15	0.9300
C6—C7	1.552 (7)	C15—C16	1.376 (10)
C6—C9	1.520 (8)	C16—H16	0.9300
C6—C10	1.558 (7)	C16—C17	1.362 (10)
C7—H7A	0.9700	C17—H17	0.9300
C7—H7B	0.9700	C17—C18	1.382 (8)
C7—C8	1.529 (8)	C18—H18	0.9300

O1—C1—H1B	110.7	C6—C10—H10A	109.1
O1—C1—H1A	110.7	C7—C6—C10	113.7 (4)
O1—C1—C2	105.2 (4)	C7—C8—H8A	108.6
O1—C4—C3	109.7 (4)	C7—C8—H8B	108.6
O2—C4—O1	121.8 (5)	H7A—C7—H7B	107.4
O2—C4—C3	128.6 (5)	C8—C2—C1	116.7 (4)
O3—C5—C3	123.2 (4)	C8—C2—H2	107.9
O3—C5—C6	124.5 (5)	C8—C2—C3	115.3 (4)
N1—C10—C6	112.7 (4)	C8—C7—C6	115.7 (4)
N1—C10—H10B	109.1	C8—C7—H7A	108.4
N1—C10—H10A	109.1	C8—C7—H7B	108.4
N1—C11—C3	108.4 (4)	H8A—C8—H8B	107.6
N1—C11—H11B	110.0	C9—C6—C7	109.4 (4)
N1—C11—H11A	110.0	C9—C6—C10	109.6 (4)
N1—C12—H12B	107.9	H9B—C9—H9A	109.5
N1—C12—H12A	107.9	H9B—C9—H9C	109.5
N1—C12—C13	117.5 (4)	H9A—C9—H9C	109.5
C1—C2—H2	107.9	C10—N1—C12	114.5 (4)
C1—C2—C3	100.4 (4)	H10B—C10—H10A	107.8
H1B—C1—H1A	108.8	C11—N1—C10	112.2 (4)
C2—C1—H1B	110.7	C11—N1—C12	113.5 (4)
C2—C1—H1A	110.7	C11—C3—C2	113.9 (4)
C2—C8—C7	114.6 (4)	H11B—C11—H11A	108.4
C2—C8—H8A	108.6	H12B—C12—H12A	107.2
C2—C8—H8B	108.6	C13—C12—H12B	107.9
C3—C2—H2	107.9	C13—C12—H12A	107.9
C3—C11—H11B	110.0	C13—C14—H14	119.8
C3—C11—H11A	110.0	C13—C18—C17	120.9 (6)
C4—O1—C1	110.2 (4)	C13—C18—H18	119.5
C4—C3—C2	101.5 (4)	C14—C13—C12	121.1 (5)
C4—C3—C5	108.9 (4)	C14—C15—H15	119.8
C4—C3—C11	115.3 (4)	C15—C14—C13	120.5 (6)
C5—C3—C2	109.9 (4)	C15—C14—H14	119.8
C5—C3—C11	107.1 (4)	C15—C16—H16	120.4
C5—C6—C7	105.6 (4)	C16—C15—C14	120.5 (6)
C5—C6—C9	112.3 (4)	C16—C15—H15	119.8
C5—C6—C10	106.2 (4)	C16—C17—H17	119.5
C6—C5—C3	112.2 (4)	C16—C17—C18	120.9 (7)
C6—C7—H7A	108.4	C17—C16—C15	119.1 (6)
C6—C7—H7B	108.4	C17—C16—H16	120.4
C6—C9—H9B	109.5	C17—C18—H18	119.5
C6—C9—H9A	109.5	C18—C13—C12	120.9 (5)
C6—C9—H9C	109.5	C18—C13—C14	118.0 (5)
C6—C10—H10B	109.1	C18—C17—H17	119.5

O1—C1—C2—C3	32.6 (5)	C5—C6—C7—C8	54.1 (6)
O1—C1—C2—C8	158.1 (4)	C5—C6—C10—N1	−53.3 (5)
O3—C5—C6—C7	117.6 (5)	C6—C7—C8—C2	−41.8 (6)
O3—C5—C6—C9	−1.6 (7)	C7—C6—C10—N1	62.4 (5)
O3—C5—C6—C10	−121.3 (5)	C8—C2—C3—C4	−160.5 (4)
N1—C12—C13—C14	−97.1 (6)	C8—C2—C3—C5	−45.4 (5)
N1—C12—C13—C18	82.4 (6)	C8—C2—C3—C11	74.9 (6)
C1—O1—C4—O2	176.2 (5)	C9—C6—C7—C8	175.2 (5)
C1—O1—C4—C3	−4.9 (6)	C9—C6—C10—N1	−174.8 (4)
C1—C2—C3—C4	−34.2 (5)	C10—N1—C11—C3	−61.7 (5)
C1—C2—C3—C5	80.9 (5)	C10—N1—C12—C13	−69.9 (6)
C1—C2—C3—C11	−158.8 (4)	C10—C6—C7—C8	−62.0 (6)
C1—C2—C8—C7	−81.1 (6)	C11—N1—C10—C6	58.3 (5)
C2—C3—C4—O1	25.5 (5)	C11—N1—C12—C13	60.8 (6)
C2—C3—C4—O2	−155.7 (6)	C11—C3—C4—O1	149.2 (4)
C2—C3—C5—O3	−120.4 (5)	C11—C3—C4—O2	−32.0 (8)
C2—C3—C5—C6	61.7 (5)	C11—C3—C5—O3	115.3 (5)
C2—C3—C11—N1	−59.9 (5)	C11—C3—C5—C6	−62.6 (4)
C3—C2—C8—C7	36.4 (6)	C12—N1—C10—C6	−170.3 (4)
C3—C5—C6—C7	−64.6 (5)	C12—N1—C11—C3	166.5 (4)
C3—C5—C6—C9	176.2 (4)	C12—C13—C14—C15	179.5 (5)
C3—C5—C6—C10	56.5 (5)	C12—C13—C18—C17	−179.0 (5)
C4—O1—C1—C2	−18.5 (6)	C13—C14—C15—C16	−0.6 (9)
C4—C3—C5—O3	−10.1 (6)	C14—C13—C18—C17	0.6 (7)
C4—C3—C5—C6	172.1 (4)	C14—C15—C16—C17	0.7 (9)
C4—C3—C11—N1	−176.7 (4)	C15—C16—C17—C18	−0.2 (9)
C5—C3—C4—O1	−90.4 (5)	C16—C17—C18—C13	−0.5 (8)
C5—C3—C4—O2	88.4 (6)	C18—C13—C14—C15	0.0 (7)
C5—C3—C11—N1	61.9 (5)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cgⁱ	0.97	2.87	3.833 (6)	169

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁NO₃
M_r	299.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	10.795 (2), 14.386 (3), 9.797 (2)
V (Å³)	1521.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Saturn 724 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10268, 1584, 1546
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.167, 1.16
No. of reflections	1584
No. of parameters	200
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16
Absolute structure	Unk

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cgⁱ	0.97	2.87	3.833 (6)	169

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

Acknowledgements

The work was supported by the National Natural Science Foundation of China (grant No. 30873147).

References

Barker, D., Brimble, M. A., Mcleod, M., Savage, G. P. & Wong, D. J. (2002). J. Chem. Soc. 7, 924–931. Google Scholar
Coates, P. A., Blagbrough, I. S., Rowan, M. G., Potter, B. V. L., Pearson, D. P. J. & Lewis, T. (1994). Tetrahedron Lett. 35, 8709–8712. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Guthmann, H., Conol, D., Wright, E., Koerber, K., Barker, D. & Brimble, M. A. (2009). Eur. J. Org. Chem. 12, 1944–1960. Web of Science CrossRef Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Weiler, L. (1970). J. Am. Chem. Soc. A92, 6702–6704. CrossRef Web of Science Google Scholar

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Volume 67| Part 3| March 2011| Page o577

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