N-[(2S)-4-Chloro-2-(l-menthyloxy)-5-oxo-2,5-dihydro-3-furyl]-l-alanine

Li, Z.; Song, X.; Wang, Z.; Yang, K.

doi:10.1107/S1600536809012720

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1030

doi:10.1107/S1600536809012720

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N-[(2S)-4-Chloro-2-(L-menthyloxy)-5-oxo-2,5-dihydro-3-furyl]-L-alanine

Zhao-yang Li,^a Xiu-mei Song,^a Zhao-yang Wang ^a ^* and Kai Yang ^a

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

(Received 17 March 2009; accepted 3 April 2009; online 10 April 2009)

The title compound, C₁₇H₂₆ClNO₅, was prepared via a tandem asymmetric Michael addition–elimination reaction of (5S)-3,4-dichloro-5-(L-menthyloxy)furan-2(5H)-one and L-alanine in the presence of potassium hydroxide. The five-membered furanone ring is approximately planar while the six-membered menthyloxy ring adopts a chair conformation. The crystal packing is stabilized by intermolecular O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For chiral 5-(L-menthyloxy)furan-2(5H)-ones as key building blocks in the synthesis of supramolecules and important natural products, see: Feringa & De Jong (1988 ); He et al. (2006 ); Lattmann et al. (1999 ). For the use of 4-aminofuran-2(5H)-one in chemical, pharmaceutical and agrochemical research, see: Kimura et al. (2000 ); Tanoury et al. (2008 ). For a related structure, see: Wang et al. (2008 ). For the synthesis of the chiral synthon (5S)-3,4-dichloro-5-(L-menthyloxy)furan-2(5H)-one, see: Chen & Geng (1993 ).

Experimental

Crystal data

C₁₇H₂₆ClNO₅
M_r = 359.84
Orthorhombic, P 2₁ 2₁ 2
a = 11.2481 (15) Å
b = 19.642 (2) Å
c = 9.0668 (11) Å
V = 2003.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.30 × 0.23 × 0.18 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.761, T_max = 0.846 (expected range = 0.866–0.962)
10244 measured reflections
3534 independent reflections
2879 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.120
S = 1.08
3534 reflections
222 parameters
312 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack (1983 ), 1499 Friedel pairs
Flack parameter: 0.00 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5ⁱ	0.86	2.20	2.975 (4)	150
O4—H4⋯O3ⁱⁱ	0.82	1.86	2.655 (3)	164
Symmetry codes: (i) -x+1, -y+2, z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536809012720/bq2134sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012720/bq2134Isup2.hkl

checkCIF report

Comment top

Chiral 5-(l-menthyloxy)-2(5H)-furanones have been extensively utilized as key building blocks in the synthesis of supramolecules and important natural products since 1980's (Feringa et al., 1988; Lattmann et al., 1999), especially in asymmetric synthesis (He et al., 2006). At the same time, 4-amino-2(5H)-furanone is an attractive moiety in chemical, pharmaceutical and agrochemical research (Kimura et al., 2000; Tanoury et al., 2008). Herein we report the crystal structure of the title compound N-[3-chloro-5-(S)-(l-menthyloxy)-2(5H)-4-furanon-yl]-L-alanine, namely C₁₇H₂₆ClNO₅, obtained via tandem asymmetric Michael addition-elimination reaction, with chiral building blocks 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone and L-alanine.

The structure of the title compound (I) is illustrated in Fig. 1. The asymmetric unit of the title compound contains two independent rings: a five-membered furanone ring and a six-membered menthyloxy ring connected each other via C1—O1—C11 ether bond, having five chiral centers (C1(R), C2(S), C5(R), C11(S), C15(S)). The furanone ring of O2—C14—C13—C12—C11 is approximately planar, whereas the cyclohexane ring displays a chair conformation with three substituents occupying equatorial positions. In addition, the molecules of (I) are linked by O4—H4···O3 and N1—H1A···O5 intermolecular hydrogen bonds, giving rise to three-dimensional structure (Tab. 1 and Fig. 2). The bond distances and angles are mostly in agreement with the expected values (Wang et al., 2008).

Related literature top

For chiral 5-(L-menthyloxy)-2(5H)-furanones as key building blocks in the synthesis of supramolecules and important natural products, see: Feringa & De Jong (1988); He et al. (2006); Lattmann et al. (1999). For the use of 4-amino-2(5H)-furanone in chemical,pharmaceutical and agrochemical research, see: Kimura et al. (2000); Tanoury et al. (2008). For a related structure, see: Wang et al. (2008). For the synthesis of the chiral synthon 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone, see: Chen & Geng (1993).

Experimental top

The chiral synthon 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone was prepared according to the literature procedure (Chen et al., 1993). After the mixture of L-alanine (0.18 g, 2.03 mmol) and potassium hydroxide (0.1274 g, 2.28 mmol) was dissolved in absolute ethyl alcohol under a nitrogen atmosphere, dichloromethane solution of 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone (0.7494 g, 2.50 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, and the pH of the solution was adjusted to 3–4 with 15% of HCl aqueous solution. 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 product, yielding (I) 0.4348 g (59.5%). ¹H NMR δ (400 MHz, CDCl₃, TMS): 0.825–0.850 (3H, m, CH₃-7), 0.901–0.955 (7H, m, CH-8, CH₃-9, 10), 0.994–1.154 (2H, m, CH₂-4), 1.340–1.439 (2H,m, CH-5, CH-2), 1.581–1.607 (3H, m, CH₃-16), 1.630–1.700 (2H, m, CH₂-3), 2.065–2.233 (2H, m, CH₂-6), 3.520–3.602 (1H, m, CH-1), 4.771–4.864 (1H, m, CH-15), 5.195 (1H, s, NH), 5.704 (1H, s, CH-11), 8.950 (1H, s, COO-H); [α]^20°_D = 53.96° (c 0.467, CH₃CH₂OH); ESI-MS, m/z (%): Calcd for C₁₇H₂₇ClNO₅⁺ ([M+H]⁺): 360.16, Found: 360.32 (95.0).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Displacement ellipsoid plot (40% probability level) of the title compound (I), with atom numbering of structurally unique non-H atoms and the H atoms.
	Fig. 2. The packing diagram of the title compound (I) (viewed down the c axis).

N-[(2S)-4-Chloro-2-(L-menthyloxy)-5-oxo- 2,5-dihydro-3-furyl]-L-alanine top

Crystal data top

C₁₇H₂₆ClNO₅	F(000) = 768.0
M_r = 359.84	D_x = 1.193 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 2460 reflections
a = 11.2481 (15) Å	θ = 2.3–20.5°
b = 19.642 (2) Å	µ = 0.21 mm⁻¹
c = 9.0668 (11) Å	T = 293 K
V = 2003.1 (4) Å³	Block, colorless
Z = 4	0.30 × 0.23 × 0.18 mm

Data collection top

Bruker APEXII area-detector diffractometer	3534 independent reflections
Radiation source: fine-focus sealed tube	2879 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scan	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→11
T_min = 0.761, T_max = 0.846	k = −23→22
10244 measured reflections	l = −10→7

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0567P)² + 0.3483P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3534 reflections	Δρ_max = 0.33 e Å⁻³
222 parameters	Δρ_min = −0.34 e Å⁻³
312 restraints	Absolute structure: Flack (1983), 1499 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (10)

Crystal data top

C₁₇H₂₆ClNO₅	V = 2003.1 (4) Å³
M_r = 359.84	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 11.2481 (15) Å	µ = 0.21 mm⁻¹
b = 19.642 (2) Å	T = 293 K
c = 9.0668 (11) Å	0.30 × 0.23 × 0.18 mm

Data collection top

Bruker APEXII area-detector diffractometer	3534 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2879 reflections with I > 2σ(I)
T_min = 0.761, T_max = 0.846	R_int = 0.037
10244 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.120	Δρ_max = 0.33 e Å⁻³
S = 1.08	Δρ_min = −0.34 e Å⁻³
3534 reflections	Absolute structure: Flack (1983), 1499 Friedel pairs
222 parameters	Absolute structure parameter: 0.00 (10)
312 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
C1	0.4798 (4)	0.78198 (19)	0.8644 (4)	0.0536 (9)
H1	0.5545	0.7992	0.8232	0.064*
C2	0.4754 (4)	0.79762 (19)	1.0295 (4)	0.0619 (10)
H2	0.3996	0.7797	1.0661	0.074*
C3	0.5733 (5)	0.7571 (2)	1.1058 (6)	0.0907 (13)
H3A	0.6499	0.7742	1.0735	0.109*
H3B	0.5677	0.7645	1.2114	0.109*
C4	0.5674 (6)	0.6817 (2)	1.0753 (6)	0.0968 (14)
H4A	0.6345	0.6594	1.1219	0.116*
H4B	0.4953	0.6633	1.1185	0.116*
C5	0.5686 (6)	0.6664 (2)	0.9133 (6)	0.0897 (13)
H5	0.6455	0.6807	0.8729	0.108*
C6	0.4707 (4)	0.70649 (18)	0.8358 (4)	0.0651 (10)
H6A	0.4756	0.6983	0.7305	0.078*
H6B	0.3940	0.6903	0.8696	0.078*
C7	0.5537 (6)	0.5895 (2)	0.8864 (7)	0.1183 (17)
H7A	0.6122	0.5650	0.9423	0.177*
H7B	0.5640	0.5799	0.7833	0.177*
H7C	0.4756	0.5756	0.9167	0.177*
C8	0.4770 (5)	0.8738 (2)	1.0660 (5)	0.0761 (12)
H8	0.4168	0.8955	1.0038	0.091*
C9	0.4415 (6)	0.8870 (3)	1.2264 (6)	0.1027 (15)
H9A	0.3749	0.8587	1.2517	0.154*
H9B	0.4200	0.9340	1.2381	0.154*
H9C	0.5072	0.8765	1.2900	0.154*
C10	0.5941 (6)	0.9084 (3)	1.0329 (7)	0.1110 (16)
H10A	0.6546	0.8904	1.0967	0.166*
H10B	0.5864	0.9565	1.0491	0.166*
H10C	0.6156	0.9001	0.9321	0.166*
C11	0.3749 (3)	0.81985 (15)	0.6456 (3)	0.0374 (7)
H11	0.4534	0.8277	0.6018	0.045*
C12	0.2880 (3)	0.87618 (15)	0.6067 (3)	0.0347 (7)
C13	0.1874 (3)	0.84593 (15)	0.5583 (4)	0.0383 (7)
C14	0.2086 (3)	0.77365 (15)	0.5426 (4)	0.0393 (7)
C15	0.2405 (3)	0.99911 (15)	0.6191 (4)	0.0427 (8)
H15	0.1863	0.9920	0.5359	0.051*
C16	0.1683 (3)	1.00945 (19)	0.7577 (5)	0.0611 (10)
H16A	0.1188	0.9704	0.7741	0.092*
H16B	0.1193	1.0492	0.7469	0.092*
H16C	0.2208	1.0154	0.8402	0.092*
C17	0.3137 (3)	1.06179 (15)	0.5905 (4)	0.0428 (8)
Cl1	0.04908 (8)	0.87823 (4)	0.51989 (12)	0.0612 (3)
N1	0.3197 (2)	0.94048 (12)	0.6313 (3)	0.0440 (7)
H1A	0.3922	0.9481	0.6563	0.053*
O1	0.3799 (2)	0.81852 (11)	0.7981 (2)	0.0423 (5)
O2	0.31972 (19)	0.75881 (10)	0.5881 (3)	0.0426 (6)
O3	0.1433 (2)	0.72965 (11)	0.4945 (3)	0.0532 (6)
O4	0.2496 (2)	1.10975 (12)	0.5305 (4)	0.0780 (10)
H4	0.2919	1.1427	0.5122	0.117*
O5	0.4163 (2)	1.06720 (11)	0.6217 (3)	0.0610 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.061 (2)	0.0474 (17)	0.0526 (19)	0.0069 (16)	−0.0111 (16)	0.0100 (15)
C2	0.080 (2)	0.0552 (19)	0.051 (2)	−0.0053 (18)	−0.0131 (18)	0.0075 (17)
C3	0.120 (3)	0.078 (2)	0.074 (2)	0.009 (2)	−0.036 (2)	0.007 (2)
C4	0.135 (3)	0.074 (3)	0.081 (3)	0.019 (3)	−0.034 (3)	0.021 (2)
C5	0.127 (3)	0.065 (2)	0.077 (3)	0.031 (2)	−0.025 (3)	0.016 (2)
C6	0.094 (3)	0.0458 (19)	0.056 (2)	0.0143 (19)	−0.0131 (19)	0.0062 (16)
C7	0.181 (4)	0.075 (3)	0.099 (3)	0.046 (3)	−0.034 (3)	0.014 (3)
C8	0.102 (3)	0.064 (2)	0.062 (2)	−0.001 (2)	−0.015 (2)	−0.005 (2)
C9	0.141 (4)	0.094 (3)	0.073 (3)	−0.006 (3)	−0.003 (3)	−0.020 (3)
C10	0.137 (4)	0.090 (3)	0.107 (3)	−0.031 (3)	−0.005 (3)	−0.008 (3)
C11	0.0426 (16)	0.0299 (15)	0.0397 (18)	−0.0006 (14)	−0.0029 (14)	0.0015 (13)
C12	0.0369 (15)	0.0272 (14)	0.0401 (17)	−0.0002 (13)	0.0019 (13)	0.0026 (13)
C13	0.0395 (16)	0.0291 (14)	0.0463 (19)	0.0002 (13)	−0.0049 (14)	−0.0001 (14)
C14	0.0437 (18)	0.0324 (16)	0.0418 (19)	−0.0012 (14)	−0.0017 (14)	−0.0025 (14)
C15	0.0397 (16)	0.0267 (15)	0.061 (2)	0.0010 (13)	−0.0075 (15)	0.0044 (15)
C16	0.053 (2)	0.048 (2)	0.083 (3)	−0.0019 (17)	0.0107 (18)	0.0009 (19)
C17	0.0399 (19)	0.0279 (15)	0.061 (2)	0.0008 (14)	−0.0058 (16)	0.0032 (15)
Cl1	0.0444 (5)	0.0433 (5)	0.0960 (8)	0.0070 (4)	−0.0225 (5)	−0.0125 (5)
N1	0.0358 (15)	0.0283 (14)	0.068 (2)	−0.0006 (12)	−0.0108 (14)	0.0035 (13)
O1	0.0457 (13)	0.0385 (12)	0.0426 (14)	0.0057 (10)	−0.0046 (10)	0.0046 (10)
O2	0.0428 (13)	0.0264 (11)	0.0585 (15)	0.0032 (10)	−0.0074 (10)	−0.0051 (10)
O3	0.0541 (14)	0.0321 (12)	0.0734 (17)	−0.0052 (11)	−0.0091 (13)	−0.0130 (12)
O4	0.0509 (15)	0.0357 (14)	0.147 (3)	−0.0056 (12)	−0.0219 (17)	0.0330 (18)
O5	0.0410 (15)	0.0330 (12)	0.109 (2)	−0.0023 (10)	−0.0109 (14)	0.0093 (14)

Geometric parameters (Å, º) top

C1—O1	1.462 (4)	C9—H9C	0.9600
C1—C6	1.509 (5)	C10—H10A	0.9600
C1—C2	1.529 (6)	C10—H10B	0.9600
C1—H1	0.9800	C10—H10C	0.9600
C2—C3	1.524 (6)	C11—O1	1.384 (4)
C2—C8	1.532 (6)	C11—O2	1.447 (4)
C2—H2	0.9800	C11—C12	1.518 (4)
C3—C4	1.509 (6)	C11—H11	0.9800
C3—H3A	0.9700	C12—N1	1.331 (4)
C3—H3B	0.9700	C12—C13	1.351 (4)
C4—C5	1.499 (8)	C13—C14	1.447 (4)
C4—H4A	0.9700	C13—Cl1	1.716 (3)
C4—H4B	0.9700	C14—O3	1.215 (4)
C5—C6	1.525 (6)	C14—O2	1.348 (4)
C5—C7	1.540 (7)	C15—N1	1.460 (4)
C5—H5	0.9800	C15—C17	1.504 (4)
C6—H6A	0.9700	C15—C16	1.510 (5)
C6—H6B	0.9700	C15—H15	0.9800
C7—H7A	0.9600	C16—H16A	0.9600
C7—H7B	0.9600	C16—H16B	0.9600
C7—H7C	0.9600	C16—H16C	0.9600
C8—C10	1.512 (7)	C17—O5	1.193 (4)
C8—C9	1.530 (7)	C17—O4	1.305 (4)
C8—H8	0.9800	N1—H1A	0.8600
C9—H9A	0.9600	O4—H4	0.8200
C9—H9B	0.9600

O1—C1—C6	111.1 (3)	C8—C9—H9A	109.5
O1—C1—C2	106.2 (3)	C8—C9—H9B	109.5
C6—C1—C2	111.3 (3)	H9A—C9—H9B	109.5
O1—C1—H1	109.4	C8—C9—H9C	109.5
C6—C1—H1	109.4	H9A—C9—H9C	109.5
C2—C1—H1	109.4	H9B—C9—H9C	109.5
C3—C2—C1	108.5 (4)	C8—C10—H10A	109.5
C3—C2—C8	113.8 (4)	C8—C10—H10B	109.5
C1—C2—C8	114.0 (3)	H10A—C10—H10B	109.5
C3—C2—H2	106.7	C8—C10—H10C	109.5
C1—C2—H2	106.7	H10A—C10—H10C	109.5
C8—C2—H2	106.7	H10B—C10—H10C	109.5
C4—C3—C2	113.4 (4)	O1—C11—O2	111.2 (2)
C4—C3—H3A	108.9	O1—C11—C12	105.8 (2)
C2—C3—H3A	108.9	O2—C11—C12	104.1 (2)
C4—C3—H3B	108.9	O1—C11—H11	111.8
C2—C3—H3B	108.9	O2—C11—H11	111.8
H3A—C3—H3B	107.7	C12—C11—H11	111.8
C5—C4—C3	112.1 (4)	N1—C12—C13	134.1 (3)
C5—C4—H4A	109.2	N1—C12—C11	118.7 (3)
C3—C4—H4A	109.2	C13—C12—C11	107.1 (3)
C5—C4—H4B	109.2	C12—C13—C14	109.0 (3)
C3—C4—H4B	109.2	C12—C13—Cl1	131.5 (2)
H4A—C4—H4B	107.9	C14—C13—Cl1	119.5 (2)
C4—C5—C6	109.9 (4)	O3—C14—O2	121.1 (3)
C4—C5—C7	110.5 (4)	O3—C14—C13	129.3 (3)
C6—C5—C7	110.8 (5)	O2—C14—C13	109.6 (3)
C4—C5—H5	108.5	N1—C15—C17	109.0 (2)
C6—C5—H5	108.5	N1—C15—C16	111.8 (3)
C7—C5—H5	108.5	C17—C15—C16	109.1 (3)
C1—C6—C5	112.3 (4)	N1—C15—H15	109.0
C1—C6—H6A	109.1	C17—C15—H15	109.0
C5—C6—H6A	109.1	C16—C15—H15	109.0
C1—C6—H6B	109.1	C15—C16—H16A	109.5
C5—C6—H6B	109.1	C15—C16—H16B	109.5
H6A—C6—H6B	107.9	H16A—C16—H16B	109.5
C5—C7—H7A	109.5	C15—C16—H16C	109.5
C5—C7—H7B	109.5	H16A—C16—H16C	109.5
H7A—C7—H7B	109.5	H16B—C16—H16C	109.5
C5—C7—H7C	109.5	O5—C17—O4	124.7 (3)
H7A—C7—H7C	109.5	O5—C17—C15	124.2 (3)
H7B—C7—H7C	109.5	O4—C17—C15	111.1 (3)
C10—C8—C9	109.9 (4)	C12—N1—C15	124.9 (3)
C10—C8—C2	114.0 (4)	C12—N1—H1A	117.5
C9—C8—C2	111.6 (4)	C15—N1—H1A	117.5
C10—C8—H8	107.0	C11—O1—C1	116.8 (3)
C9—C8—H8	107.0	C14—O2—C11	109.2 (2)
C2—C8—H8	107.0	C17—O4—H4	109.5

O1—C1—C2—C3	176.5 (3)	N1—C12—C13—Cl1	−5.9 (6)
C6—C1—C2—C3	55.4 (5)	C11—C12—C13—Cl1	170.3 (3)
O1—C1—C2—C8	−55.6 (5)	C12—C13—C14—O3	−175.4 (3)
C6—C1—C2—C8	−176.7 (4)	Cl1—C13—C14—O3	5.8 (5)
C1—C2—C3—C4	−54.8 (6)	C12—C13—C14—O2	3.1 (4)
C8—C2—C3—C4	177.1 (4)	Cl1—C13—C14—O2	−175.7 (2)
C2—C3—C4—C5	55.4 (7)	N1—C15—C17—O5	−23.0 (5)
C3—C4—C5—C6	−53.4 (7)	C16—C15—C17—O5	99.4 (4)
C3—C4—C5—C7	−176.0 (5)	N1—C15—C17—O4	158.5 (3)
O1—C1—C6—C5	−175.7 (4)	C16—C15—C17—O4	−79.2 (4)
C2—C1—C6—C5	−57.5 (5)	C13—C12—N1—C15	4.8 (6)
C4—C5—C6—C1	55.4 (6)	C11—C12—N1—C15	−171.0 (3)
C7—C5—C6—C1	177.8 (5)	C17—C15—N1—C12	−156.0 (3)
C3—C2—C8—C10	56.0 (6)	C16—C15—N1—C12	83.2 (4)
C1—C2—C8—C10	−69.1 (5)	O2—C11—O1—C1	83.7 (3)
C3—C2—C8—C9	−69.2 (6)	C12—C11—O1—C1	−163.9 (3)
C1—C2—C8—C9	165.7 (4)	C6—C1—O1—C11	−67.5 (4)
O1—C11—C12—N1	69.8 (3)	C2—C1—O1—C11	171.3 (3)
O2—C11—C12—N1	−172.9 (3)	O3—C14—O2—C11	−177.5 (3)
O1—C11—C12—C13	−107.0 (3)	C13—C14—O2—C11	3.8 (3)
O2—C11—C12—C13	10.2 (3)	O1—C11—O2—C14	105.0 (3)
N1—C12—C13—C14	175.6 (3)	C12—C11—O2—C14	−8.4 (3)
C11—C12—C13—C14	−8.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.86	2.20	2.975 (4)	150
O4—H4···O3ⁱⁱ	0.82	1.86	2.655 (3)	164

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₆ClNO₅
M_r	359.84
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	11.2481 (15), 19.642 (2), 9.0668 (11)
V (Å³)	2003.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.30 × 0.23 × 0.18

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.761, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	10244, 3534, 2879
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.120, 1.08
No. of reflections	3534
No. of parameters	222
No. of restraints	312
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.34
Absolute structure	Flack (1983), 1499 Friedel pairs
Absolute structure parameter	0.00 (10)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.86	2.20	2.975 (4)	150.4
O4—H4···O3ⁱⁱ	0.82	1.86	2.655 (3)	163.7

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

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

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