tert-Butyl 5-(4-methoxy­phen­yl)-1-methyl-2-oxopyrrolidin-3-yl carbonate

Mohammat, M.F.; Shaameri, Z.; Hamzah, A.S.; Fun, H.-K.; Chantrapromma, S.

doi:10.1107/S1600536808005527

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages o661-o662

doi:10.1107/S1600536808005527

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tert-Butyl 5-(4-methoxyphenyl)-1-methyl-2-oxopyrrolidin-3-yl carbonate

M. Fazli Mohammat,^a Zurina Shaameri,^a A. Sazali Hamzah,^a Hoong-Kun Fun ^b ^* and Suchada Chantrapromma ^c ‡

^aInstitute of Science, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 5 February 2008; accepted 27 February 2008; online 5 March 2008)

In the title compound, C₁₇H₂₃NO₅, the pyrrolidinone ring is in an envelope conformation. The tert-butyl carbonate and 4-methoxyphenyl groups are arranged on the same side of the pyrrolidinone ring. The methoxy group is coplanar with the attached benzene ring. The molecules are linked into chains along the b axis via C—H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ). For ring conformations, see: Cremer & Pople (1975 ). For the biological properties of pyrrolidine alkaloids, see: Iida et al. (1986 ); Matkhalikova et al. (1969 ); Reddy & Rao (2006 ); Royles (1996 ). For syntheses of compounds containing a tetramic acid ring, see: Chandrasekhar et al. (2005 , 2006 ); Gurjar et al. (2006 ); Yoda et al. (1996 ). For a related structure, see: Mohammat et al. (2008 ).

Experimental

Crystal data

C₁₇H₂₃NO₅
M_r = 321.36
Monoclinic, C 2/c
a = 23.9157 (4) Å
b = 6.2788 (1) Å
c = 24.1224 (4) Å
β = 101.971 (1)°
V = 3543.49 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100.0 (1) K
0.49 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.958, T_max = 0.986
21759 measured reflections
5155 independent reflections
3632 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.125
S = 1.09
5155 reflections
213 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	1.00	2.35	2.9633 (15)	119
C4—H4⋯O1ⁱⁱ	1.00	2.56	3.5238 (15)	162
C11—H11A⋯O1	0.98	2.47	2.8652 (16)	104
C15—H15A⋯O3	0.98	2.45	3.011 (3)	116
C16—H16B⋯O3	0.98	2.44	2.9904 (19)	115
C17—H17A⋯O3ⁱⁱⁱ	0.98	2.38	3.324 (2)	161
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y-1, z; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005527/ci2562sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005527/ci2562Isup2.hkl

checkCIF report

Comment top

Chiral polyhydroxy alkaloids show remarkable biological properties. Among these, pyrrolidine alkaloids carrying an aromatic substituent on the ring are of a rare class found in nature (Reddy & Rao, 2006). The title compound, C₁₇H₂₃NO₅, can act as an essential intermediate in the synthesis of such a hydroxyl alkaloid unit (Chandrasekhar et al., 2005; 2006; Gurjar et al., 2006; Yoda et al., 1996), which eventually can be used as a template in multi-step syntheses of natural products such as codonopsinine isolated from Codonopsis clematidae. Codonopsinine exhibits antibiotic and hypotensive activities without affecting the central nervous system (Matkhalikova et al., 1969). We have synthesized the title compound and its structure is reported here.

The molecular structure of the title compound is shown in Fig. 1. The pyrrolidinone ring adopts an envelope conformation, with atom C3 displaced from the C1/C2/C4/N1 plane by 0.310 (2) Å; the puckering parameters (Cremer & Pople, 1975) are Q = 0.194 (1) Å and ϕ = 111.1 (4)°. The methoxy group is coplanar with the benzene ring as indicated by the torsion angle C17–O5–C8–C7 of -2.06 (19)°. In the tert-butylcarbonate moiety, atoms C12, C13, C14, O2, O3 and O4 lie on the same plane, with O4 deviating by a maximum of 0.019 (1) Å. All bond lengths and angles show normal values (Allen et al., 1987) and are comparable with those observed in a related structure (Mohammat et al., 2008).

Weak C—H···O intramolecular interactions are observed in the molecular structure. In the crystal packing (Fig. 2), the molecules are linked into chains along the b axis via C2—H2···O1ⁱ, C4—H4···O1ⁱⁱ and C17—H17A···O3ⁱⁱⁱ hydrogen bonds (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For biological properties of pyrrolidine alkaloids, see: Iida et al. (1986); Matkhalikova et al. (1969); Reddy & Rao (2006); Royles (1996). For syntheses of compounds containing a tetramic acid ring, see: Chandrasekhar et al. (2005, 2006); Gurjar et al. (2006); Yoda et al. (1996). For a related structure, see: Mohammat et al. (2008).

Experimental top

Equimolar amount of diethyloxalacetate sodium salt (20.00 g, 95.2 mmol), anisaldehyde (11.60 ml, 95.2 mmol) and methylamine (11.74 ml, 95.2 mmol) in ethanol (200 ml) was refluxed to obtain an α,β-diketo ester (7.78 g, 28%). Diethoxycarbonylation of this α,β-diketo ester (2.62 g, 8.94 mmol) was then successfully carried out by refluxing in 10% HCl solution to give a basic pyrrolidinone ring skeleton (0.86 g, 44%). Reduction of this diketone (0.32 g, 1.46 mmol) was carried out in sodium borohydride/methanol at 273 K to give the hydroxy keto amide (0.29 g, 92%). Protection of the hydroxyl group (0.29 g, 1.3 mmol) was successfully carried out using tert-butoxycarbonyl (Boc₂O), and 4-dimethylaminopyridine (DMAP) in tetrahydrofuran (THF) via stirring at room temperature for 24 h to obtain the title compound in 76% yield (0.31 g). Colourless block-shaped single crystals suitable for X-ray structure determination were obtained by slow evaporation of an ethyl acetate-petroleum ether (1:1 v/v) solution after several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the b axis. Hydrogen bonds are shown as dashed lines.

tert-Butyl 5-(4-methoxyphenyl)-1-methyl-2-oxopyrrolidin-3-yl carbonate top

Crystal data top

C₁₇H₂₃NO₅	F(000) = 1376
M_r = 321.36	D_x = 1.205 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5155 reflections
a = 23.9157 (4) Å	θ = 1.7–30.0°
b = 6.2788 (1) Å	µ = 0.09 mm⁻¹
c = 24.1224 (4) Å	T = 100 K
β = 101.971 (1)°	Block, colourless
V = 3543.49 (10) Å³	0.49 × 0.18 × 0.16 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5155 independent reflections
Radiation source: fine-focus sealed tube	3632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.7°
ω scans	h = −33→33
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
T_min = 0.958, T_max = 0.986	l = −33→33
21759 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0546P)² + 0.7489P] where P = (F_o² + 2F_c²)/3
5155 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₂₃NO₅	V = 3543.49 (10) Å³
M_r = 321.36	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.9157 (4) Å	µ = 0.09 mm⁻¹
b = 6.2788 (1) Å	T = 100 K
c = 24.1224 (4) Å	0.49 × 0.18 × 0.16 mm
β = 101.971 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5155 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3632 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.986	R_int = 0.035
21759 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.10	Δρ_max = 0.30 e Å⁻³
5155 reflections	Δρ_min = −0.27 e Å⁻³
213 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.74746 (4)	1.13213 (14)	0.78815 (4)	0.0273 (2)
O2	0.62826 (4)	1.08149 (14)	0.74372 (3)	0.0269 (2)
O3	0.58372 (4)	0.94891 (18)	0.65973 (4)	0.0389 (3)
O4	0.55809 (4)	1.25800 (16)	0.69566 (4)	0.0339 (2)
O5	0.63462 (4)	0.40108 (16)	1.02990 (4)	0.0344 (2)
N1	0.73427 (4)	0.81417 (16)	0.83037 (4)	0.0214 (2)
C1	0.72075 (5)	0.9674 (2)	0.79119 (5)	0.0210 (2)
C2	0.66622 (5)	0.90078 (19)	0.75060 (5)	0.0215 (2)
H2	0.6747	0.8586	0.7132	0.026*
C3	0.64411 (5)	0.7111 (2)	0.77840 (5)	0.0264 (3)
H3A	0.6300	0.5991	0.7501	0.032*
H3B	0.6125	0.7541	0.7968	0.032*
C4	0.69576 (5)	0.6296 (2)	0.82289 (5)	0.0212 (2)
H4	0.7142	0.5077	0.8068	0.025*
C5	0.68121 (5)	0.56408 (19)	0.87850 (5)	0.0207 (2)
C6	0.69206 (5)	0.3607 (2)	0.89980 (5)	0.0237 (3)
H6	0.7095	0.2605	0.8792	0.028*
C7	0.67799 (5)	0.2985 (2)	0.95081 (5)	0.0261 (3)
H7	0.6861	0.1583	0.9649	0.031*
C8	0.65208 (5)	0.4434 (2)	0.98043 (5)	0.0260 (3)
C9	0.64158 (6)	0.6501 (2)	0.96005 (5)	0.0301 (3)
H9	0.6243	0.7505	0.9807	0.036*
C10	0.65630 (5)	0.7092 (2)	0.90992 (5)	0.0273 (3)
H10	0.6494	0.8510	0.8965	0.033*
C11	0.78953 (5)	0.8054 (2)	0.86899 (6)	0.0310 (3)
H11A	0.8114	0.9339	0.8644	0.046*
H11B	0.8105	0.6795	0.8605	0.046*
H11C	0.7840	0.7970	0.9081	0.046*
C12	0.58881 (5)	1.0836 (2)	0.69533 (5)	0.0235 (3)
C13	0.50992 (5)	1.3048 (2)	0.64753 (6)	0.0335 (3)
C14	0.48639 (8)	1.5091 (3)	0.66671 (10)	0.0726 (7)
H14A	0.4732	1.4835	0.7020	0.109*
H14B	0.4543	1.5585	0.6374	0.109*
H14C	0.5164	1.6179	0.6732	0.109*
C15	0.53223 (8)	1.3349 (4)	0.59443 (9)	0.0818 (8)
H15A	0.5462	1.1985	0.5830	0.123*
H15B	0.5636	1.4383	0.6014	0.123*
H15C	0.5015	1.3878	0.5642	0.123*
C16	0.46593 (6)	1.1316 (3)	0.64296 (8)	0.0547 (5)
H16A	0.4571	1.1058	0.6803	0.082*
H16B	0.4808	1.0008	0.6293	0.082*
H16C	0.4311	1.1753	0.6163	0.082*
C17	0.64211 (8)	0.1904 (3)	1.05145 (7)	0.0444 (4)
H17A	0.6283	0.1816	1.0869	0.067*
H17B	0.6828	0.1530	1.0586	0.067*
H17C	0.6204	0.0913	1.0237	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0283 (5)	0.0219 (5)	0.0342 (5)	−0.0031 (4)	0.0121 (4)	0.0018 (4)
O2	0.0266 (4)	0.0269 (5)	0.0260 (4)	0.0102 (4)	0.0026 (3)	−0.0026 (4)
O3	0.0367 (5)	0.0479 (7)	0.0282 (5)	0.0156 (5)	−0.0021 (4)	−0.0096 (5)
O4	0.0270 (5)	0.0296 (5)	0.0414 (5)	0.0104 (4)	−0.0019 (4)	−0.0008 (4)
O5	0.0511 (6)	0.0321 (6)	0.0239 (4)	−0.0066 (5)	0.0167 (4)	−0.0021 (4)
N1	0.0198 (5)	0.0218 (5)	0.0217 (5)	−0.0030 (4)	0.0023 (4)	0.0007 (4)
C1	0.0222 (5)	0.0204 (6)	0.0224 (6)	0.0020 (5)	0.0098 (4)	−0.0017 (5)
C2	0.0228 (6)	0.0201 (6)	0.0216 (5)	0.0064 (5)	0.0046 (4)	−0.0001 (5)
C3	0.0241 (6)	0.0279 (7)	0.0248 (6)	−0.0042 (5)	−0.0002 (5)	0.0015 (5)
C4	0.0234 (6)	0.0180 (6)	0.0222 (6)	−0.0025 (5)	0.0050 (4)	−0.0011 (5)
C5	0.0202 (5)	0.0207 (6)	0.0210 (5)	−0.0027 (5)	0.0037 (4)	−0.0009 (5)
C6	0.0260 (6)	0.0212 (6)	0.0250 (6)	0.0007 (5)	0.0075 (5)	−0.0001 (5)
C7	0.0316 (6)	0.0206 (6)	0.0262 (6)	−0.0006 (5)	0.0064 (5)	0.0019 (5)
C8	0.0294 (6)	0.0281 (7)	0.0209 (6)	−0.0071 (5)	0.0060 (5)	−0.0031 (5)
C9	0.0389 (7)	0.0252 (7)	0.0287 (6)	−0.0007 (6)	0.0128 (5)	−0.0065 (6)
C10	0.0347 (7)	0.0208 (6)	0.0272 (6)	0.0004 (5)	0.0083 (5)	−0.0003 (5)
C11	0.0228 (6)	0.0358 (8)	0.0312 (7)	−0.0027 (6)	−0.0014 (5)	0.0025 (6)
C12	0.0206 (5)	0.0274 (7)	0.0240 (6)	0.0037 (5)	0.0083 (5)	0.0038 (5)
C13	0.0204 (6)	0.0369 (8)	0.0409 (8)	0.0074 (6)	0.0011 (5)	0.0119 (6)
C14	0.0545 (11)	0.0502 (12)	0.0977 (16)	0.0303 (10)	−0.0199 (11)	−0.0041 (11)
C15	0.0520 (10)	0.134 (2)	0.0651 (12)	0.0401 (13)	0.0254 (9)	0.0665 (14)
C16	0.0263 (7)	0.0538 (11)	0.0761 (12)	−0.0002 (7)	−0.0078 (7)	0.0168 (10)
C17	0.0646 (10)	0.0396 (9)	0.0351 (8)	−0.0043 (8)	0.0242 (7)	0.0091 (7)

Geometric parameters (Å, º) top

O1—C1	1.2257 (15)	C7—H7	0.95
O2—C12	1.3403 (14)	C8—C9	1.3917 (19)
O2—C2	1.4411 (14)	C9—C10	1.3788 (18)
O3—C12	1.1934 (15)	C9—H9	0.95
O4—C12	1.3195 (15)	C10—H10	0.95
O4—C13	1.4854 (15)	C11—H11A	0.98
O5—C8	1.3694 (15)	C11—H11B	0.98
O5—C17	1.4188 (18)	C11—H11C	0.98
N1—C1	1.3404 (15)	C13—C15	1.498 (2)
N1—C11	1.4516 (15)	C13—C16	1.501 (2)
N1—C4	1.4679 (15)	C13—C14	1.512 (2)
C1—C2	1.5182 (16)	C14—H14A	0.98
C2—C3	1.5150 (18)	C14—H14B	0.98
C2—H2	1.00	C14—H14C	0.98
C3—C4	1.5459 (16)	C15—H15A	0.98
C3—H3A	0.99	C15—H15B	0.98
C3—H3B	0.99	C15—H15C	0.98
C4—C5	1.5112 (16)	C16—H16A	0.98
C4—H4	1.00	C16—H16B	0.98
C5—C6	1.3807 (17)	C16—H16C	0.98
C5—C10	1.3951 (17)	C17—H17A	0.98
C6—C7	1.3970 (17)	C17—H17B	0.98
C6—H6	0.95	C17—H17C	0.98
C7—C8	1.3807 (18)

C12—O2—C2	114.90 (9)	C9—C10—C5	121.08 (12)
C12—O4—C13	120.12 (11)	C9—C10—H10	119.5
C8—O5—C17	117.54 (11)	C5—C10—H10	119.5
C1—N1—C11	122.27 (10)	N1—C11—H11A	109.5
C1—N1—C4	115.26 (9)	N1—C11—H11B	109.5
C11—N1—C4	120.90 (10)	H11A—C11—H11B	109.5
O1—C1—N1	126.54 (11)	N1—C11—H11C	109.5
O1—C1—C2	125.62 (11)	H11A—C11—H11C	109.5
N1—C1—C2	107.83 (10)	H11B—C11—H11C	109.5
O2—C2—C3	113.61 (10)	O3—C12—O4	128.22 (11)
O2—C2—C1	107.08 (9)	O3—C12—O2	124.61 (11)
C3—C2—C1	105.26 (9)	O4—C12—O2	107.17 (10)
O2—C2—H2	110.2	O4—C13—C15	109.70 (11)
C3—C2—H2	110.2	O4—C13—C16	109.42 (12)
C1—C2—H2	110.2	C15—C13—C16	113.41 (17)
C2—C3—C4	105.40 (9)	O4—C13—C14	101.90 (12)
C2—C3—H3A	110.7	C15—C13—C14	112.05 (16)
C4—C3—H3A	110.7	C16—C13—C14	109.72 (14)
C2—C3—H3B	110.7	C13—C14—H14A	109.5
C4—C3—H3B	110.7	C13—C14—H14B	109.5
H3A—C3—H3B	108.8	H14A—C14—H14B	109.5
N1—C4—C5	111.08 (9)	C13—C14—H14C	109.5
N1—C4—C3	102.39 (10)	H14A—C14—H14C	109.5
C5—C4—C3	114.10 (10)	H14B—C14—H14C	109.5
N1—C4—H4	109.7	C13—C15—H15A	109.5
C5—C4—H4	109.7	C13—C15—H15B	109.5
C3—C4—H4	109.7	H15A—C15—H15B	109.5
C6—C5—C10	118.05 (11)	C13—C15—H15C	109.5
C6—C5—C4	121.46 (11)	H15A—C15—H15C	109.5
C10—C5—C4	120.49 (11)	H15B—C15—H15C	109.5
C5—C6—C7	121.68 (12)	C13—C16—H16A	109.5
C5—C6—H6	119.2	C13—C16—H16B	109.5
C7—C6—H6	119.2	H16A—C16—H16B	109.5
C8—C7—C6	119.19 (12)	C13—C16—H16C	109.5
C8—C7—H7	120.4	H16A—C16—H16C	109.5
C6—C7—H7	120.4	H16B—C16—H16C	109.5
O5—C8—C7	125.01 (12)	O5—C17—H17A	109.5
O5—C8—C9	115.06 (12)	O5—C17—H17B	109.5
C7—C8—C9	119.93 (12)	H17A—C17—H17B	109.5
C10—C9—C8	120.04 (12)	O5—C17—H17C	109.5
C10—C9—H9	120.0	H17A—C17—H17C	109.5
C8—C9—H9	120.0	H17B—C17—H17C	109.5

C11—N1—C1—O1	−12.17 (19)	C3—C4—C5—C10	−58.06 (15)
C4—N1—C1—O1	−177.97 (11)	C10—C5—C6—C7	0.94 (18)
C11—N1—C1—C2	167.57 (11)	C4—C5—C6—C7	−179.13 (11)
C4—N1—C1—C2	1.77 (13)	C5—C6—C7—C8	0.63 (18)
C12—O2—C2—C3	−88.44 (12)	C17—O5—C8—C7	−2.06 (19)
C12—O2—C2—C1	155.79 (10)	C17—O5—C8—C9	177.48 (13)
O1—C1—C2—O2	−48.13 (15)	C6—C7—C8—O5	177.96 (11)
N1—C1—C2—O2	132.13 (10)	C6—C7—C8—C9	−1.56 (19)
O1—C1—C2—C3	−169.34 (11)	O5—C8—C9—C10	−178.65 (12)
N1—C1—C2—C3	10.92 (12)	C7—C8—C9—C10	0.9 (2)
O2—C2—C3—C4	−135.30 (10)	C8—C9—C10—C5	0.7 (2)
C1—C2—C3—C4	−18.46 (12)	C6—C5—C10—C9	−1.61 (18)
C1—N1—C4—C5	−135.47 (11)	C4—C5—C10—C9	178.45 (11)
C11—N1—C4—C5	58.52 (14)	C13—O4—C12—O3	0.5 (2)
C1—N1—C4—C3	−13.27 (13)	C13—O4—C12—O2	−179.21 (10)
C11—N1—C4—C3	−179.29 (11)	C2—O2—C12—O3	0.52 (18)
C2—C3—C4—N1	18.89 (12)	C2—O2—C12—O4	−179.77 (9)
C2—C3—C4—C5	139.01 (11)	C12—O4—C13—C15	−63.23 (18)
N1—C4—C5—C6	−122.88 (12)	C12—O4—C13—C16	61.79 (16)
C3—C4—C5—C6	122.01 (12)	C12—O4—C13—C14	177.89 (14)
N1—C4—C5—C10	57.05 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	1.00	2.35	2.9633 (15)	119
C4—H4···O1ⁱⁱ	1.00	2.56	3.5238 (15)	162
C11—H11A···O1	0.98	2.47	2.8652 (16)	104
C15—H15A···O3	0.98	2.45	3.011 (3)	116
C16—H16B···O3	0.98	2.44	2.9904 (19)	115
C17—H17A···O3ⁱⁱⁱ	0.98	2.38	3.324 (2)	161

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x, y−1, z; (iii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₃NO₅
M_r	321.36
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	23.9157 (4), 6.2788 (1), 24.1224 (4)
β (°)	101.971 (1)
V (Å³)	3543.49 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.49 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.958, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	21759, 5155, 3632
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.125, 1.10
No. of reflections	5155
No. of parameters	213
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	1.00	2.3481	2.9633 (15)	119
C4—H4···O1ⁱⁱ	1.00	2.5582	3.5238 (15)	162
C11—H11A···O1	0.98	2.4706	2.8652 (16)	104
C15—H15A···O3	0.98	2.4491	3.011 (3)	116
C16—H16B···O3	0.98	2.4401	2.9904 (19)	115
C17—H17A···O3ⁱⁱⁱ	0.98	2.3815	3.324 (2)	161

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x, y−1, z; (iii) x, −y+1, z+1/2.

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

The authors acknowledge the generous support of Universiti Teknologi MARA and Universiti Sains Malaysia, and the financial support of the Ministry of Science, Technology and Innovation (E-Science grant No. SF0050–02-01–01). HKF and SC thank the Malaysian Government and Universiti Sains Malaysia for the Scientific Advancement Grant Allocation (SAGA) grant No. 304/PFIZIK/653003/A118.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chandrasekhar, S., Jagadeshwar, V. & Prakash, S. J. (2005). Tetrahedron Lett. 46, 3127–3129. Web of Science CrossRef CAS Google Scholar
Chandrasekhar, S., Saritha, B., Jagadeshwar, V. & Prakash, S. J. (2006). Tetrahedron Asymmetry, 17, 1380–1386. Web of Science CrossRef CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Gurjar, M. K., Borhade, R. G., Puranik, V. G. & Ramana, C. V. (2006). Tetrahedron Lett. 47, 6979–6981. Web of Science CSD CrossRef CAS Google Scholar
Iida, H., Yamazaki, N. & Kibayashi, C. (1986). Tetrahedron Lett. 27, 5393–5396. CSD CrossRef Web of Science Google Scholar
Matkhalikova, S. F., Malikov, V. M. & Yunusov, S. Y. (1969). Chem Abstr. 71, 13245z. Google Scholar
Mohammat, M. F., Shaameri, Z., Hamzah, A. S., Fun, H.-K. & Chantrapromma, S. (2008). Acta Cryst. E64, o578–o579. Web of Science CSD CrossRef IUCr Journals Google Scholar
Reddy, J. S. & Rao, B. V. (2006). J. Org. Chem. 76, 2224–2227. Google Scholar
Royles, B. J. L. (1996). Chem. Rev. 95, 1961–2001. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yoda, H., Nakajima, T. & Takabe, K. (1996). Tetrahedron Lett. 31, 5531–5534. CrossRef Web of Science Google Scholar