(5S)-3-Chloro-4-diallyl­amino-5-[(1R,2S,5R)-2-isopropyl-5-methyl­cyclo­hex­yloxy]furan-2(5H)-one

Huang, D.-N.; Tan, Y.-H.; Fu, J.-H.; Wang, Z.-Y.

doi:10.1107/S1600536811027772

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2050

doi:10.1107/S1600536811027772

Open

access

(5S)-3-Chloro-4-diallylamino-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one

Dong-Na Huang,^a Yue-He Tan,^a Jian-Hua Fu ^a and Zhao-Yang Wang ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: wangwangzhaoyang@tom.com

(Received 7 July 2011; accepted 11 July 2011; online 16 July 2011)

The title compound, C₂₀H₃₀ClNO₃, was obtained via a tandem asymmetric Michael addition–elimination reaction of (5S)-3,4-dichloro-5-(l-menthyloxy)-2(5H)-furanone and diallylamine in the presence of potassium fluoride. The molecular structure contains an approximately planar five-membered furanone ring [maximum atomic deviation = 0.0221 (3) Å] and a six-membered ring adopting a chair conformation.

Related literature

For the biological activity of 4-amino-2(5H)-furanones, see: Gondela & Walczak (2010 ). For chemical, pharmaceutical and agrochemical applications of 3,4-amino-2(5H)-furanones, see: Tanoury et al. (2008 ); Kimura et al. (2000 ). For the synthesis of optically pure 5-(l-menthyloxy)-3,4-dichloro-2(5H)-furanones, see: Song et al. (2009 ). For the use of intermediate chiral 5-S-(l-menthyloxy)-2(5H)-furanones, see: Hoffmann et al. (2006 ).

Experimental

Crystal data

C₂₀H₃₀ClNO₃
M_r = 367.90
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.4540 (17) Å
b = 11.722 (2) Å
c = 20.648 (4) Å
V = 2046.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 273 K
0.23 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.954, T_max = 0.968
9931 measured reflections
3950 independent reflections
2923 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.102
S = 0.97
3950 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ), 1677 Friedel pairs
Flack parameter: −0.06 (6)

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536811027772/zq2113sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027772/zq2113Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811027772/zq2113Isup3.cml

checkCIF report

Comment top

The 2(5H)-furanone moiety is present in many natural products exhibiting various biological activities, namely antibiotic cytotoxic and antitumor (Gondela & Walczak, 2010). Recently, owing to their specific activity and high stereoselectivity, chiral 5S-(l-menthyloxy)-2(5H)-furanones have emerged as significant synthetic intermediates (Hoffmann et al., 2006; Song et al., 2009). At the same time, 4-amino-2(5H)-furanone (or 3-amino-2(5H)-furanone) is a kind of attractive moiety in chemical, pharmaceutical and agrochemical research (Tanoury et al., 2008; Kimura et al., 2000). Therefore we were interested in the tandem Michael addition-elimination reaction of the chiral synthon 3,4-dichloro-5(S)-(l-menthyloxy)-2(5H)-furanone and diallylamine in the present of potassium fluoride which yielded the title compound, C₂₀H₃₀ClNO₃, illustrated in Fig. 1.

The title compound has four chiral centers [C4(S), C7(R), C9(R), C11(S)] and contains a five-membered furanone ring and a six-membered ring connected to each other via a C11—O1—C9 ether bond. The furanone ring of C11—O2—C12—C13—C14 is approximately planar [maximum atomic deviation 0.0221 (3) Å], whereas the six-membered ring displays a chair conformation.

Related literature top

For the biological activity of 4-amino-2(5H)-furanones, see: Gondela et al. (2010). For applications of 3,4-amino-2(5H)-furanone in chemical, pharmaceutical and agrochemical fields, see: Tanoury et al. (2008); Kimura et al. (2000). For the synthesis of optically pure 5-(l-menthyloxy)-3,4-dichloro-2(5H)-furanones, see: Song et al. (2009). For the use of intermediate chiral 5-S-(l-menthyloxy)-2(5H)-furanones, see: Hoffmann et al. (2006).

Experimental top

The precursor 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone was prepared according to the literature procedure (Song et al., 2009). After the mixture of 3,4-dichloro-5S-(l-menthyloxy)-2(5H)-furanone (2.0 mmol) and potassium fluoride (6.0 mmol) was dissolved in absolute tetrahydrofuran (2.0 ml) under nitrogen atmosphere, tetrahydrofuran solution of diallylamine (3.0 mmol) was added. The reaction was carried out under the stirring at room temperature for 24 h. Once the reaction was complete, the solvents were removed under reduced pressure. The residual solid was dissolved in dichloromethane. Then the combined organic layers from extraction were concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography with the gradient mixture of petroleum ether and ethyl acetate to give the final product (0.575 g, 78.3%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 thermal ellipsoids drawn at the 50% probability level.
	Fig. 2. Perspective view of the crystal packing.

(5S)-3-Chloro-4-diallylamino-5-[(1R,2S,5R)-2- isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one top

Crystal data top

C₂₀H₃₀ClNO₃	F(000) = 792.0
M_r = 367.90	D_x = 1.194 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2994 reflections
a = 8.4540 (17) Å	θ = 2.6–22.1°
b = 11.722 (2) Å	µ = 0.20 mm⁻¹
c = 20.648 (4) Å	T = 273 K
V = 2046.1 (7) Å³	Block, colourless
Z = 4	0.23 × 0.20 × 0.16 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3950 independent reflections
Radiation source: fine-focus sealed tube	2923 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
phi and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→8
T_min = 0.954, T_max = 0.968	k = −14→14
9931 measured reflections	l = −22→25

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0584P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.102	(Δ/σ)_max < 0.001
S = 0.97	Δρ_max = 0.11 e Å⁻³
3950 reflections	Δρ_min = −0.13 e Å⁻³
230 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0125 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1677 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.06 (6)

Crystal data top

C₂₀H₃₀ClNO₃	V = 2046.1 (7) Å³
M_r = 367.90	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.4540 (17) Å	µ = 0.20 mm⁻¹
b = 11.722 (2) Å	T = 273 K
c = 20.648 (4) Å	0.23 × 0.20 × 0.16 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3950 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2923 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.968	R_int = 0.033
9931 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.102	Δρ_max = 0.11 e Å⁻³
S = 0.97	Δρ_min = −0.13 e Å⁻³
3950 reflections	Absolute structure: Flack (1983), 1677 Friedel pairs
230 parameters	Absolute structure parameter: −0.06 (6)
0 restraints

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
Cl1	0.27814 (9)	0.46092 (4)	0.91712 (3)	0.0767 (2)
C14	0.3852 (2)	0.68664 (15)	0.92440 (10)	0.0450 (5)
C12	0.3084 (3)	0.60235 (16)	1.01887 (11)	0.0553 (5)
C13	0.3270 (3)	0.58965 (15)	0.95061 (10)	0.0513 (5)
C11	0.3995 (3)	0.77169 (15)	0.97949 (9)	0.0455 (5)
H11	0.5078	0.8009	0.9827	0.055*
C4	0.2172 (3)	1.05546 (15)	0.97288 (11)	0.0560 (5)
H4	0.1096	1.0295	0.9827	0.067*
C8	0.3116 (3)	0.95600 (17)	1.07345 (10)	0.0595 (6)
H8A	0.3896	0.9024	1.0895	0.071*
H8B	0.2077	0.9252	1.0830	0.071*
C9	0.3297 (3)	0.96703 (16)	1.00113 (9)	0.0496 (5)
H9	0.4389	0.9890	0.9911	0.060*
C6	0.2206 (4)	1.1564 (2)	1.08117 (14)	0.0844 (8)
H6A	0.2396	1.2296	1.1017	0.101*
H6B	0.1125	1.1341	1.0905	0.101*
C19	0.6469 (3)	0.81529 (18)	0.81335 (11)	0.0645 (6)
H19	0.7300	0.7852	0.8374	0.077*
C5	0.2408 (4)	1.16881 (17)	1.00889 (14)	0.0805 (8)
H5A	0.3461	1.1976	0.9999	0.097*
H5B	0.1652	1.2242	0.9928	0.097*
C18	0.4919 (3)	0.82587 (17)	0.84594 (11)	0.0591 (6)
H18A	0.5042	0.8718	0.8847	0.071*
H18B	0.4189	0.8652	0.8174	0.071*
C20	0.6762 (4)	0.8440 (2)	0.75483 (13)	0.0879 (9)
H20A	0.5963	0.8744	0.7291	0.105*
H20B	0.7774	0.8345	0.7380	0.105*
C15	0.3794 (3)	0.6432 (2)	0.80906 (11)	0.0696 (7)
H15A	0.3966	0.5640	0.8207	0.083*
H15B	0.4479	0.6606	0.7727	0.083*
C3	0.2284 (3)	1.06627 (18)	0.89904 (12)	0.0692 (7)
H3	0.2244	0.9886	0.8815	0.083*
C2	0.0861 (4)	1.1300 (3)	0.87141 (16)	0.1021 (11)
H2A	0.0887	1.1263	0.8250	0.153*
H2B	0.0897	1.2083	0.8850	0.153*
H2C	−0.0096	1.0954	0.8869	0.153*
C7	0.3313 (3)	1.0696 (2)	1.10909 (12)	0.0737 (8)
H7	0.4397	1.0964	1.1019	0.088*
C17	0.1074 (4)	0.7219 (3)	0.81581 (15)	0.0960 (10)
H17A	0.1338	0.7650	0.8521	0.115*
H17B	0.0053	0.7251	0.7991	0.115*
C16	0.2130 (5)	0.6574 (3)	0.78848 (13)	0.0877 (9)
H16	0.1808	0.6161	0.7524	0.105*
C1	0.3837 (4)	1.1195 (3)	0.87538 (15)	0.0915 (9)
H1A	0.4714	1.0808	0.8952	0.137*
H1B	0.3862	1.1988	0.8870	0.137*
H1C	0.3908	1.1121	0.8292	0.137*
C10	0.3083 (5)	1.0534 (3)	1.18160 (13)	0.1167 (12)
H10A	0.2053	1.0221	1.1896	0.175*
H10B	0.3177	1.1258	1.2030	0.175*
H10C	0.3876	1.0023	1.1979	0.175*
O1	0.29340 (17)	0.86000 (10)	0.96896 (6)	0.0459 (3)
O3	0.2592 (2)	0.53592 (13)	1.05869 (8)	0.0787 (5)
O2	0.3578 (2)	0.70923 (11)	1.03625 (6)	0.0578 (4)
N1	0.4245 (2)	0.71508 (14)	0.86380 (8)	0.0535 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0780 (5)	0.0447 (3)	0.1075 (5)	−0.0086 (3)	0.0051 (4)	−0.0110 (3)
C14	0.0359 (12)	0.0431 (10)	0.0560 (12)	0.0047 (8)	0.0009 (10)	−0.0023 (9)
C12	0.0476 (14)	0.0461 (11)	0.0721 (14)	0.0114 (10)	0.0083 (12)	0.0082 (10)
C13	0.0499 (14)	0.0391 (10)	0.0650 (13)	0.0052 (9)	0.0028 (11)	−0.0034 (9)
C11	0.0420 (13)	0.0424 (10)	0.0520 (11)	0.0048 (8)	0.0026 (10)	0.0002 (9)
C4	0.0468 (13)	0.0410 (10)	0.0802 (14)	0.0021 (9)	0.0065 (12)	0.0006 (9)
C8	0.0590 (15)	0.0544 (12)	0.0651 (13)	0.0027 (11)	0.0038 (12)	−0.0137 (10)
C9	0.0429 (12)	0.0384 (9)	0.0676 (13)	−0.0027 (9)	0.0066 (10)	−0.0081 (9)
C6	0.0707 (19)	0.0605 (13)	0.122 (2)	0.0036 (13)	0.0113 (19)	−0.0395 (14)
C19	0.0649 (17)	0.0676 (14)	0.0611 (14)	−0.0026 (11)	0.0068 (12)	0.0045 (11)
C5	0.0714 (18)	0.0416 (11)	0.128 (2)	0.0022 (11)	0.0092 (18)	−0.0092 (12)
C18	0.0696 (18)	0.0510 (12)	0.0567 (13)	−0.0041 (11)	0.0104 (12)	−0.0008 (9)
C20	0.102 (3)	0.0845 (18)	0.0771 (18)	0.0078 (16)	0.0255 (17)	0.0160 (13)
C15	0.085 (2)	0.0660 (14)	0.0577 (13)	−0.0072 (13)	0.0093 (14)	−0.0186 (11)
C3	0.0683 (18)	0.0532 (12)	0.0860 (17)	0.0052 (11)	0.0083 (14)	0.0154 (11)
C2	0.097 (3)	0.093 (2)	0.117 (2)	0.0256 (18)	−0.001 (2)	0.0334 (19)
C7	0.0587 (18)	0.0717 (15)	0.0907 (18)	−0.0038 (12)	0.0042 (14)	−0.0356 (13)
C17	0.072 (2)	0.112 (2)	0.103 (2)	0.0005 (18)	−0.0199 (19)	0.0284 (19)
C16	0.095 (3)	0.097 (2)	0.0713 (17)	−0.0248 (18)	−0.0220 (18)	0.0032 (14)
C1	0.091 (2)	0.0711 (17)	0.112 (2)	0.0002 (15)	0.0313 (18)	0.0273 (16)
C10	0.132 (3)	0.124 (2)	0.095 (2)	0.017 (2)	−0.009 (2)	−0.0571 (18)
O1	0.0451 (9)	0.0361 (6)	0.0566 (8)	0.0029 (6)	−0.0014 (7)	−0.0035 (5)
O3	0.0931 (14)	0.0606 (9)	0.0823 (11)	0.0075 (10)	0.0270 (10)	0.0186 (8)
O2	0.0713 (11)	0.0498 (8)	0.0524 (8)	0.0084 (7)	0.0055 (8)	0.0020 (6)
N1	0.0601 (13)	0.0492 (9)	0.0512 (10)	−0.0060 (8)	0.0077 (9)	−0.0074 (8)

Geometric parameters (Å, º) top

Cl1—C13	1.711 (2)	C5—H5B	0.9700
C14—N1	1.337 (3)	C18—N1	1.466 (3)
C14—C13	1.352 (3)	C18—H18A	0.9700
C14—C11	1.517 (3)	C18—H18B	0.9700
C12—O3	1.206 (2)	C20—H20A	0.9300
C12—O2	1.369 (2)	C20—H20B	0.9300
C12—C13	1.426 (3)	C15—N1	1.460 (3)
C11—O1	1.387 (2)	C15—C16	1.479 (4)
C11—O2	1.426 (2)	C15—H15A	0.9700
C11—H11	0.9800	C15—H15B	0.9700
C4—C9	1.523 (3)	C3—C2	1.526 (4)
C4—C3	1.533 (3)	C3—C1	1.534 (4)
C4—C5	1.536 (3)	C3—H3	0.9800
C4—H4	0.9800	C2—H2A	0.9600
C8—C9	1.507 (3)	C2—H2B	0.9600
C8—C7	1.530 (3)	C2—H2C	0.9600
C8—H8A	0.9700	C7—C10	1.521 (4)
C8—H8B	0.9700	C7—H7	0.9800
C9—O1	1.452 (2)	C17—C16	1.299 (4)
C9—H9	0.9800	C17—H17A	0.9300
C6—C7	1.498 (4)	C17—H17B	0.9300
C6—C5	1.509 (4)	C16—H16	0.9300
C6—H6A	0.9700	C1—H1A	0.9600
C6—H6B	0.9700	C1—H1B	0.9600
C19—C20	1.279 (3)	C1—H1C	0.9600
C19—C18	1.478 (4)	C10—H10A	0.9600
C19—H19	0.9300	C10—H10B	0.9600
C5—H5A	0.9700	C10—H10C	0.9600

N1—C14—C13	132.44 (19)	C19—C18—H18B	109.1
N1—C14—C11	121.21 (17)	H18A—C18—H18B	107.8
C13—C14—C11	106.34 (18)	C19—C20—H20A	120.0
O3—C12—O2	121.2 (2)	C19—C20—H20B	120.0
O3—C12—C13	130.1 (2)	H20A—C20—H20B	120.0
O2—C12—C13	108.72 (17)	N1—C15—C16	113.9 (2)
C14—C13—C12	110.37 (18)	N1—C15—H15A	108.8
C14—C13—Cl1	131.91 (17)	C16—C15—H15A	108.8
C12—C13—Cl1	117.71 (15)	N1—C15—H15B	108.8
O1—C11—O2	110.64 (16)	C16—C15—H15B	108.8
O1—C11—C14	108.76 (15)	H15A—C15—H15B	107.7
O2—C11—C14	105.02 (15)	C2—C3—C4	111.3 (2)
O1—C11—H11	110.8	C2—C3—C1	110.9 (2)
O2—C11—H11	110.8	C4—C3—C1	113.8 (2)
C14—C11—H11	110.8	C2—C3—H3	106.8
C9—C4—C3	113.48 (18)	C4—C3—H3	106.8
C9—C4—C5	108.78 (19)	C1—C3—H3	106.8
C3—C4—C5	113.70 (18)	C3—C2—H2A	109.5
C9—C4—H4	106.8	C3—C2—H2B	109.5
C3—C4—H4	106.8	H2A—C2—H2B	109.5
C5—C4—H4	106.8	C3—C2—H2C	109.5
C9—C8—C7	113.01 (18)	H2A—C2—H2C	109.5
C9—C8—H8A	109.0	H2B—C2—H2C	109.5
C7—C8—H8A	109.0	C6—C7—C10	112.5 (2)
C9—C8—H8B	109.0	C6—C7—C8	109.8 (2)
C7—C8—H8B	109.0	C10—C7—C8	110.6 (2)
H8A—C8—H8B	107.8	C6—C7—H7	107.9
O1—C9—C8	110.96 (15)	C10—C7—H7	107.9
O1—C9—C4	106.29 (16)	C8—C7—H7	107.9
C8—C9—C4	111.98 (17)	C16—C17—H17A	120.0
O1—C9—H9	109.2	C16—C17—H17B	120.0
C8—C9—H9	109.2	H17A—C17—H17B	120.0
C4—C9—H9	109.2	C17—C16—C15	126.5 (3)
C7—C6—C5	112.0 (2)	C17—C16—H16	116.8
C7—C6—H6A	109.2	C15—C16—H16	116.8
C5—C6—H6A	109.2	C3—C1—H1A	109.5
C7—C6—H6B	109.2	C3—C1—H1B	109.5
C5—C6—H6B	109.2	H1A—C1—H1B	109.5
H6A—C6—H6B	107.9	C3—C1—H1C	109.5
C20—C19—C18	125.4 (3)	H1A—C1—H1C	109.5
C20—C19—H19	117.3	H1B—C1—H1C	109.5
C18—C19—H19	117.3	C7—C10—H10A	109.5
C6—C5—C4	112.37 (19)	C7—C10—H10B	109.5
C6—C5—H5A	109.1	H10A—C10—H10B	109.5
C4—C5—H5A	109.1	C7—C10—H10C	109.5
C6—C5—H5B	109.1	H10A—C10—H10C	109.5
C4—C5—H5B	109.1	H10B—C10—H10C	109.5
H5A—C5—H5B	107.9	C11—O1—C9	115.87 (15)
N1—C18—C19	112.65 (18)	C12—O2—C11	109.26 (15)
N1—C18—H18A	109.1	C14—N1—C15	121.05 (18)
C19—C18—H18A	109.1	C14—N1—C18	123.58 (16)
N1—C18—H18B	109.1	C15—N1—C18	114.71 (17)

N1—C14—C13—C12	178.7 (2)	C9—C4—C3—C1	−69.3 (2)
C11—C14—C13—C12	−2.5 (2)	C5—C4—C3—C1	55.8 (3)
N1—C14—C13—Cl1	−0.1 (4)	C5—C6—C7—C10	−178.1 (2)
C11—C14—C13—Cl1	178.66 (18)	C5—C6—C7—C8	−54.5 (3)
O3—C12—C13—C14	179.4 (2)	C9—C8—C7—C6	54.1 (3)
O2—C12—C13—C14	−0.8 (2)	C9—C8—C7—C10	178.8 (2)
O3—C12—C13—Cl1	−1.6 (3)	N1—C15—C16—C17	−3.2 (4)
O2—C12—C13—Cl1	178.22 (15)	O2—C11—O1—C9	87.69 (19)
N1—C14—C11—O1	65.3 (2)	C14—C11—O1—C9	−157.46 (15)
C13—C14—C11—O1	−113.67 (19)	C8—C9—O1—C11	−68.4 (2)
N1—C14—C11—O2	−176.28 (18)	C4—C9—O1—C11	169.65 (16)
C13—C14—C11—O2	4.8 (2)	O3—C12—O2—C11	−176.1 (2)
C7—C8—C9—O1	−173.88 (18)	C13—C12—O2—C11	4.0 (2)
C7—C8—C9—C4	−55.3 (3)	O1—C11—O2—C12	111.83 (19)
C3—C4—C9—O1	−56.8 (2)	C14—C11—O2—C12	−5.3 (2)
C5—C4—C9—O1	175.58 (18)	C13—C14—N1—C15	12.0 (4)
C3—C4—C9—C8	−178.10 (18)	C11—C14—N1—C15	−166.6 (2)
C5—C4—C9—C8	54.3 (2)	C13—C14—N1—C18	−177.8 (2)
C7—C6—C5—C4	57.3 (3)	C11—C14—N1—C18	3.6 (3)
C9—C4—C5—C6	−55.5 (3)	C16—C15—N1—C14	79.1 (3)
C3—C4—C5—C6	177.0 (2)	C16—C15—N1—C18	−91.9 (3)
C20—C19—C18—N1	115.5 (3)	C19—C18—N1—C14	122.4 (2)
C9—C4—C3—C2	164.5 (2)	C19—C18—N1—C15	−66.8 (3)
C5—C4—C3—C2	−70.4 (3)

Experimental details

Crystal data
Chemical formula	C₂₀H₃₀ClNO₃
M_r	367.90
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	273
a, b, c (Å)	8.4540 (17), 11.722 (2), 20.648 (4)
V (Å³)	2046.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.23 × 0.20 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.954, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	9931, 3950, 2923
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 0.97
No. of reflections	3950
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.13
Absolute structure	Flack (1983), 1677 Friedel pairs
Absolute structure parameter	−0.06 (6)

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

The work was supported by the National Natural Science Foundation of China (grant No. 20772035) and the Natural Science Foundation of Guangdong Province, China (grant No. 5300082).

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gondela, E. & Walczak, K. Z. (2010). Eur. J. Med. Chem. 45, 3993–3997. Web of Science CrossRef CAS PubMed Google Scholar
Hoffmann, N., Bertrand, S., Marinkovi, S. & Pesch, J. (2006). Pure Appl. Chem. 78, 2227–2246. Web of Science CrossRef CAS Google Scholar
Kimura, Y., Mizuno, T., Kawano, T., Okada, K. & Shimad, A. (2000). Phytochemistry, 53, 829–831. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, X.-M., Wang, Z.-Y., Li, J.-X. & Fu, J.-H. (2009). Chin. J. Org. Chem. 11, 1804–1810. Google Scholar
Tanoury, G. J., Chen, M.-Z., Dong, Y., Forslund, R. E. & Magdziak, D. (2008). Org. Lett. 10, 185–188. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.