(1S*,4′S*,5R*)-1-Isopropyl-5-meth­oxy-2′,3-dimethyl-4,6-dioxa-2-aza­spiro­[bicyclo­[3.2.0]hept-2-ene-7,4′-isoquinoline]-1′,3′(2′H,4′H)-dione

Fun, H.-K.; Quah, C.K.; Huang, C.; Yu, H.

doi:10.1107/S1600536811015315

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1271-o1272

doi:10.1107/S1600536811015315

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(1S,4′S,5R*)-1-Isopropyl-5-methoxy-2′,3-dimethyl-4,6-dioxa-2-azaspiro[bicyclo[3.2.0]hept-2-ene-7,4′-isoquinoline]-1′,3′(2′H,4′H)-dione

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Chengmei Huang ^b and Haitao Yu ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, People's Republic of China
^*Correspondence e-mail: hkfun@usm.my

(Received 15 April 2011; accepted 22 April 2011; online 29 April 2011)

In the isoquinoline ring system of the title molecule, C₁₈H₂₀N₂O₅, the N-heterocyclic ring is in a half-boat conformation. The dioxa-2-azaspiro ring is essentially planar, with a maximum deviation of 0.029 (1) Å, and makes a dihedral angle of 30.63 (5)° with the benzene ring. The molecular structure is stabilized by a weak intramolecular C—H⋯O hydrogen bond, which generates a S(6) ring motif. In the crystal, molecules are linked via weak intermolecular C—H⋯O hydrogen bonds into a three-dimensional supramolecular network. Additional stabilization is provided by π–π stacking interactions between symmetry-related benzene rings with a centroid–centroid distance of 3.6507 (5) Å.

Related literature

For general background to and the potential biological activity of the title compound, see: Pollers-Wieers et al. (1981 ); Malamas et al. (1994 ); Yu et al. (2010 ); Du et al. (2008 ); Chen et al. (2006 ); Zhang et al. (2006 ); Mitchell et al. (1995 , 2000 ); Harris et al. (2005 ); Wang et al. (2010 ); Huang et al. (2011 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For standard bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₅
M_r = 344.36
Monoclinic, P 2₁ /c
a = 10.5721 (2) Å
b = 10.4260 (2) Å
c = 15.7633 (3) Å
β = 101.641 (1)°
V = 1701.77 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.51 × 0.37 × 0.35 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.951, T_max = 0.966
23124 measured reflections
6242 independent reflections
5286 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.108
S = 1.02
6242 reflections
231 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2ⁱ	0.93	2.59	3.3754 (12)	143
C15—H15A⋯O5	0.96	2.56	3.2151 (12)	126
C18—H18A⋯O1ⁱⁱ	0.96	2.58	3.4298 (13)	148
C18—H18C⋯O2ⁱⁱⁱ	0.96	2.58	3.3641 (12)	139
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015315/lh5237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015315/lh5237Isup2.hkl

checkCIF report

Comment top

Isoquinolines are often found in bioactive natural products. They have been used to build blocks of benzo[c]phenanthridine alkaloids (Pollers-Wieers et al., 1981; Malamas et al., 1994; Yu et al., 2010). Isoquinoline-1,3,4-trione derivatives were reported to be a type of small molecular inhibitor against caspase-3 which can promote apoptosis of the cells (Du et al., 2008; Chen et al., 2006). They can also attenuate apoptosis of neuronal cells induced by β-amyloid.(Zhang et al., 2006). Isoquinoline-1,3,4-trione and its derivatives have been reported to be redox mediators of photosystems and have been used as herbicides (Mitchell et al., 2000; 1995). Oxazole rings are also found in some bioactive natural products such as Annuloline and Ostreogrycin A. Oxazoles can be used to inhibit the activity of malignant tumors (Harris et al., 2005). Since a lot of natural products especially the alkaloids containing the isoquinoline or oxazole ring are bioactive, there has been intense development of methodology to construct such moieties (Wang et al., 2010). The title compound which was derived from isoquinoline-1,3,4-trione and oxazoles (Huang et al., 2011) may have potential use in biochemical and pharmaceutical fields. Due to the importance of the isoquinoline-1,3,4-trione derivatives, we report herein the crystal structure of the title compound with a relative configuration of (1S^*, 4'S^*, 5R^*).

In the title racemic compound, Fig. 1, atoms C9, C10 and C12 are the chiral centers. The isoquinoline ring system (N1/C1-C9) is not completely planar, the N-heterocyclic ring (N1/C1-C3/C8/C9) being distorted towards a half-boat conformation with atom C1 deviating by 0.243 (1) Å from the mean plane through the remaining atoms, puckering parameters (Cremer & Pople, 1975) Q = 0.2843 (9) Å, Θ = 64.10 (18)° and ϕ =100.97 (19)°. The dioxa-2-azaspiro ring (N2/O4/C10-C12) is essentially planar [maximum deviation of 0.029 (1) Å at atoms O4 and C10] and it inclines at a dihedral angle of 30.63 (5)° with the benzene ring (C3-C8). Bond lengths (Allen et al., 1987) and angles are within normal ranges. The molecular structure is stabilized by a weak intramolecular C15–H15A···O5 hydrogen bond (Table 1) which generates a S(6) ring motif (Fig. 1, Bernstein et al., 1995).

In the crystal structure, Fig. 2, molecules are linked via intermolecular C6–H6A···O2ⁱ, C18–H18A···O1ⁱⁱ and C18–H18C···O2ⁱⁱⁱ hydrogen bonds (Table 1) into a three-dimensional supramolecular network. The crystal packing is further consolidated by π–π stacking interactions between the centroids of the C3-C8 (Cg1) rings, with a Cg1···Cg1^iv distance of 3.6507 (5) Å [symmetry code: (iv) 1-x, 1-y, -z].

Related literature top

For general background to and the potential biological activity of the title compound, see: Pollers-Wieers et al. (1981); Malamas et al. (1994); Yu et al. (2010); Du et al. (2008); Chen et al. (2006); Zhang et al. (2006); Mitchell et al. (1995, 2000); Harris et al. (2005); Wang et al. (2010); Huang et al. (2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental top

The title compound was the main product from the photoreaction between isoquinoline-1,3,4-trione and 4-isopropyl-5-methoxy-2-methyloxazole. The compound was purified by flash column chromatography with ethyl acetate/petroleum ether (1:4) as eluents. X-ray quality crystals of the title compound was obtained from slow evaporation of an acetone and petroleum ether solution (1:5) (m.p. 451-453 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms. Intramolecular interaction is shown as dash line.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

(1S*,4'S*,5R*)-1-Isopropyl-5-methoxy-2',3-dimethyl- 4,6-dioxa-2-azaspiro[bicyclo[3.2.0]hept-2-ene-7,4'-isoquinoline]- 1',3'(2'H,4'H)-dione top

Crystal data top

C₁₈H₂₀N₂O₅	F(000) = 728
M_r = 344.36	D_x = 1.344 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9966 reflections
a = 10.5721 (2) Å	θ = 2.6–32.7°
b = 10.4260 (2) Å	µ = 0.10 mm⁻¹
c = 15.7633 (3) Å	T = 100 K
β = 101.641 (1)°	Block, colourless
V = 1701.77 (6) Å³	0.51 × 0.37 × 0.35 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6242 independent reflections
Radiation source: fine-focus sealed tube	5286 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 32.7°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→15
T_min = 0.951, T_max = 0.966	k = −10→15
23124 measured reflections	l = −23→23

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0531P)² + 0.4865P] where P = (F_o² + 2F_c²)/3
6242 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₅	V = 1701.77 (6) Å³
M_r = 344.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5721 (2) Å	µ = 0.10 mm⁻¹
b = 10.4260 (2) Å	T = 100 K
c = 15.7633 (3) Å	0.51 × 0.37 × 0.35 mm
β = 101.641 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6242 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5286 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.966	R_int = 0.026
23124 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.02	Δρ_max = 0.49 e Å⁻³
6242 reflections	Δρ_min = −0.21 e Å⁻³
231 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.83725 (6)	0.47548 (7)	0.19496 (4)	0.01927 (13)
O2	0.43236 (7)	0.35091 (9)	0.21065 (5)	0.03015 (18)
O3	0.80900 (6)	0.41336 (6)	0.02423 (4)	0.01457 (12)
O4	1.01024 (6)	0.31366 (6)	0.07000 (4)	0.01661 (12)
O5	0.88314 (6)	0.26083 (6)	−0.06194 (4)	0.01730 (13)
N1	0.64083 (7)	0.39850 (8)	0.20730 (4)	0.01585 (14)
N2	0.90028 (7)	0.20947 (7)	0.15999 (5)	0.01627 (14)
C1	0.74047 (8)	0.41697 (8)	0.16262 (5)	0.01427 (14)
C2	0.51566 (8)	0.36231 (9)	0.16792 (5)	0.01791 (16)
C3	0.48885 (8)	0.34408 (8)	0.07267 (5)	0.01483 (15)
C4	0.36037 (8)	0.32910 (9)	0.02963 (6)	0.01775 (16)
H4A	0.2944	0.3288	0.0608	0.021*
C5	0.33188 (9)	0.31473 (9)	−0.05953 (6)	0.01878 (16)
H5A	0.2467	0.3038	−0.0883	0.023*
C6	0.43059 (9)	0.31659 (9)	−0.10635 (5)	0.01847 (16)
H6A	0.4110	0.3070	−0.1662	0.022*
C7	0.55824 (8)	0.33279 (8)	−0.06381 (5)	0.01616 (15)
H7A	0.6237	0.3353	−0.0953	0.019*
C8	0.58806 (8)	0.34536 (8)	0.02622 (5)	0.01330 (14)
C9	0.72502 (8)	0.35261 (8)	0.07458 (5)	0.01283 (14)
C10	0.88181 (8)	0.29935 (8)	0.01999 (5)	0.01360 (14)
C11	1.00499 (8)	0.26235 (9)	0.14963 (5)	0.01693 (15)
C12	0.80770 (8)	0.22272 (8)	0.07841 (5)	0.01327 (14)
C13	0.73890 (8)	0.09734 (8)	0.04853 (6)	0.01698 (15)
H13A	0.6784	0.1133	−0.0063	0.020*
C14	0.66170 (10)	0.04867 (9)	0.11444 (7)	0.02400 (19)
H14A	0.5977	0.1111	0.1211	0.036*
H14B	0.7190	0.0350	0.1692	0.036*
H14C	0.6200	−0.0306	0.0944	0.036*
C15	0.83697 (10)	−0.00346 (9)	0.03243 (7)	0.02421 (19)
H15A	0.8840	0.0289	−0.0091	0.036*
H15B	0.7923	−0.0805	0.0105	0.036*
H15C	0.8960	−0.0218	0.0858	0.036*
C16	0.66478 (10)	0.43923 (10)	0.29833 (5)	0.02245 (18)
H16A	0.7481	0.4091	0.3275	0.034*
H16B	0.5994	0.4041	0.3259	0.034*
H16C	0.6625	0.5312	0.3012	0.034*
C17	0.92704 (10)	0.35916 (10)	−0.11451 (6)	0.02420 (19)
H17A	0.9248	0.3263	−0.1717	0.036*
H17B	1.0138	0.3836	−0.0887	0.036*
H17C	0.8715	0.4326	−0.1180	0.036*
C18	1.12452 (9)	0.27703 (11)	0.21661 (6)	0.0258 (2)
H18A	1.1267	0.2126	0.2604	0.039*
H18B	1.1258	0.3605	0.2425	0.039*
H18C	1.1984	0.2675	0.1904	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0165 (3)	0.0212 (3)	0.0188 (3)	−0.0030 (2)	0.0004 (2)	−0.0021 (2)
O2	0.0189 (3)	0.0524 (5)	0.0207 (3)	−0.0037 (3)	0.0078 (3)	0.0031 (3)
O3	0.0144 (3)	0.0141 (3)	0.0161 (2)	0.0000 (2)	0.0054 (2)	0.0029 (2)
O4	0.0117 (3)	0.0213 (3)	0.0163 (3)	−0.0018 (2)	0.0016 (2)	0.0039 (2)
O5	0.0197 (3)	0.0188 (3)	0.0144 (2)	−0.0020 (2)	0.0057 (2)	−0.0007 (2)
N1	0.0148 (3)	0.0204 (3)	0.0121 (3)	0.0003 (3)	0.0024 (2)	0.0008 (2)
N2	0.0133 (3)	0.0188 (3)	0.0162 (3)	0.0017 (3)	0.0017 (2)	0.0049 (2)
C1	0.0139 (3)	0.0147 (3)	0.0137 (3)	0.0012 (3)	0.0016 (3)	0.0012 (3)
C2	0.0150 (4)	0.0221 (4)	0.0165 (3)	0.0003 (3)	0.0028 (3)	0.0025 (3)
C3	0.0131 (3)	0.0149 (3)	0.0158 (3)	−0.0002 (3)	0.0013 (3)	0.0012 (3)
C4	0.0130 (4)	0.0179 (4)	0.0215 (4)	−0.0006 (3)	0.0015 (3)	0.0021 (3)
C5	0.0152 (4)	0.0159 (4)	0.0224 (4)	−0.0013 (3)	−0.0030 (3)	0.0006 (3)
C6	0.0200 (4)	0.0164 (4)	0.0165 (3)	0.0010 (3)	−0.0023 (3)	−0.0010 (3)
C7	0.0171 (4)	0.0162 (4)	0.0144 (3)	0.0016 (3)	0.0014 (3)	−0.0004 (3)
C8	0.0131 (3)	0.0117 (3)	0.0143 (3)	0.0003 (3)	0.0008 (3)	0.0010 (2)
C9	0.0119 (3)	0.0137 (3)	0.0128 (3)	−0.0008 (3)	0.0025 (2)	0.0015 (2)
C10	0.0120 (3)	0.0148 (3)	0.0138 (3)	−0.0005 (3)	0.0022 (2)	0.0009 (3)
C11	0.0150 (4)	0.0190 (4)	0.0164 (3)	0.0011 (3)	0.0020 (3)	0.0038 (3)
C12	0.0112 (3)	0.0140 (3)	0.0145 (3)	0.0002 (3)	0.0025 (2)	0.0023 (3)
C13	0.0147 (4)	0.0132 (3)	0.0233 (4)	−0.0006 (3)	0.0045 (3)	0.0011 (3)
C14	0.0217 (4)	0.0165 (4)	0.0366 (5)	−0.0006 (3)	0.0126 (4)	0.0057 (4)
C15	0.0219 (4)	0.0153 (4)	0.0372 (5)	0.0019 (3)	0.0104 (4)	−0.0001 (3)
C16	0.0236 (4)	0.0310 (5)	0.0125 (3)	0.0002 (4)	0.0033 (3)	−0.0012 (3)
C17	0.0298 (5)	0.0280 (5)	0.0174 (4)	−0.0049 (4)	0.0107 (3)	0.0023 (3)
C18	0.0161 (4)	0.0359 (5)	0.0224 (4)	−0.0038 (4)	−0.0032 (3)	0.0084 (4)

Geometric parameters (Å, º) top

O1—C1	1.2118 (10)	C7—H7A	0.9300
O2—C2	1.2176 (11)	C8—C9	1.4960 (11)
O3—C10	1.4250 (10)	C9—C12	1.6063 (12)
O3—C9	1.4504 (10)	C10—C12	1.5464 (11)
O4—C11	1.3759 (10)	C11—C18	1.4822 (12)
O4—C10	1.4336 (10)	C12—C13	1.5237 (12)
O5—C10	1.3553 (10)	C13—C14	1.5314 (13)
O5—C17	1.4520 (11)	C13—C15	1.5330 (13)
N1—C1	1.3937 (11)	C13—H13A	0.9800
N1—C2	1.3955 (11)	C14—H14A	0.9600
N1—C16	1.4686 (11)	C14—H14B	0.9600
N2—C11	1.2764 (11)	C14—H14C	0.9600
N2—C12	1.4569 (10)	C15—H15A	0.9600
C1—C9	1.5203 (11)	C15—H15B	0.9600
C2—C3	1.4830 (12)	C15—H15C	0.9600
C3—C8	1.3950 (11)	C16—H16A	0.9600
C3—C4	1.3991 (12)	C16—H16B	0.9600
C4—C5	1.3849 (12)	C16—H16C	0.9600
C4—H4A	0.9300	C17—H17A	0.9600
C5—C6	1.3947 (13)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C6—C7	1.3907 (12)	C18—H18A	0.9600
C6—H6A	0.9300	C18—H18B	0.9600
C7—C8	1.3965 (11)	C18—H18C	0.9600

C10—O3—C9	93.30 (6)	N2—C11—C18	126.18 (8)
C11—O4—C10	104.66 (6)	O4—C11—C18	115.10 (8)
C10—O5—C17	113.61 (7)	N2—C12—C13	112.66 (7)
C1—N1—C2	123.92 (7)	N2—C12—C10	104.11 (6)
C1—N1—C16	117.07 (7)	C13—C12—C10	121.79 (7)
C2—N1—C16	118.29 (7)	N2—C12—C9	112.13 (6)
C11—N2—C12	106.96 (7)	C13—C12—C9	119.31 (7)
O1—C1—N1	121.13 (7)	C10—C12—C9	83.07 (6)
O1—C1—C9	122.16 (7)	C12—C13—C14	111.17 (7)
N1—C1—C9	116.58 (7)	C12—C13—C15	110.04 (7)
O2—C2—N1	120.47 (8)	C14—C13—C15	110.86 (8)
O2—C2—C3	122.39 (8)	C12—C13—H13A	108.2
N1—C2—C3	117.09 (7)	C14—C13—H13A	108.2
C8—C3—C4	120.38 (7)	C15—C13—H13A	108.2
C8—C3—C2	121.32 (7)	C13—C14—H14A	109.5
C4—C3—C2	118.28 (8)	C13—C14—H14B	109.5
C5—C4—C3	119.69 (8)	H14A—C14—H14B	109.5
C5—C4—H4A	120.2	C13—C14—H14C	109.5
C3—C4—H4A	120.2	H14A—C14—H14C	109.5
C4—C5—C6	120.19 (8)	H14B—C14—H14C	109.5
C4—C5—H5A	119.9	C13—C15—H15A	109.5
C6—C5—H5A	119.9	C13—C15—H15B	109.5
C7—C6—C5	120.23 (8)	H15A—C15—H15B	109.5
C7—C6—H6A	119.9	C13—C15—H15C	109.5
C5—C6—H6A	119.9	H15A—C15—H15C	109.5
C6—C7—C8	119.97 (8)	H15B—C15—H15C	109.5
C6—C7—H7A	120.0	N1—C16—H16A	109.5
C8—C7—H7A	120.0	N1—C16—H16B	109.5
C3—C8—C7	119.53 (7)	H16A—C16—H16B	109.5
C3—C8—C9	119.08 (7)	N1—C16—H16C	109.5
C7—C8—C9	121.29 (7)	H16A—C16—H16C	109.5
O3—C9—C8	112.32 (6)	H16B—C16—H16C	109.5
O3—C9—C1	109.99 (6)	O5—C17—H17A	109.5
C8—C9—C1	113.71 (7)	O5—C17—H17B	109.5
O3—C9—C12	90.01 (6)	H17A—C17—H17B	109.5
C8—C9—C12	116.10 (6)	O5—C17—H17C	109.5
C1—C9—C12	112.35 (6)	H17A—C17—H17C	109.5
O5—C10—O3	113.67 (7)	H17B—C17—H17C	109.5
O5—C10—O4	111.35 (7)	C11—C18—H18A	109.5
O3—C10—O4	110.37 (6)	C11—C18—H18B	109.5
O5—C10—C12	121.22 (7)	H18A—C18—H18B	109.5
O3—C10—C12	93.42 (6)	C11—C18—H18C	109.5
O4—C10—C12	105.29 (6)	H18A—C18—H18C	109.5
N2—C11—O4	118.71 (7)	H18B—C18—H18C	109.5

C2—N1—C1—O1	162.97 (9)	C17—O5—C10—O4	−70.72 (9)
C16—N1—C1—O1	−7.11 (12)	C17—O5—C10—C12	164.67 (8)
C2—N1—C1—C9	−21.02 (12)	C9—O3—C10—O5	122.71 (7)
C16—N1—C1—C9	168.91 (7)	C9—O3—C10—O4	−111.37 (6)
C1—N1—C2—O2	−178.18 (9)	C9—O3—C10—C12	−3.67 (6)
C16—N1—C2—O2	−8.22 (14)	C11—O4—C10—O5	−138.23 (7)
C1—N1—C2—C3	−0.57 (13)	C11—O4—C10—O3	94.54 (7)
C16—N1—C2—C3	169.39 (8)	C11—O4—C10—C12	−5.10 (8)
O2—C2—C3—C8	−173.71 (9)	C12—N2—C11—O4	−1.58 (11)
N1—C2—C3—C8	8.73 (12)	C12—N2—C11—C18	177.19 (9)
O2—C2—C3—C4	8.11 (14)	C10—O4—C11—N2	4.53 (11)
N1—C2—C3—C4	−169.45 (8)	C10—O4—C11—C18	−174.37 (8)
C8—C3—C4—C5	0.38 (13)	C11—N2—C12—C13	132.03 (8)
C2—C3—C4—C5	178.58 (8)	C11—N2—C12—C10	−1.88 (9)
C3—C4—C5—C6	−0.71 (13)	C11—N2—C12—C9	−90.04 (8)
C4—C5—C6—C7	0.05 (13)	O5—C10—C12—N2	131.75 (8)
C5—C6—C7—C8	0.95 (13)	O3—C10—C12—N2	−107.82 (6)
C4—C3—C8—C7	0.61 (12)	O4—C10—C12—N2	4.38 (8)
C2—C3—C8—C7	−177.53 (8)	O5—C10—C12—C13	3.21 (12)
C4—C3—C8—C9	−175.90 (8)	O3—C10—C12—C13	123.64 (8)
C2—C3—C8—C9	5.95 (12)	O4—C10—C12—C13	−124.16 (8)
C6—C7—C8—C3	−1.27 (12)	O5—C10—C12—C9	−117.10 (8)
C6—C7—C8—C9	175.16 (8)	O3—C10—C12—C9	3.33 (5)
C10—O3—C9—C8	−114.88 (7)	O4—C10—C12—C9	115.52 (6)
C10—O3—C9—C1	117.40 (7)	O3—C9—C12—N2	99.19 (7)
C10—O3—C9—C12	3.52 (6)	C8—C9—C12—N2	−145.79 (7)
C3—C8—C9—O3	−152.15 (7)	C1—C9—C12—N2	−12.51 (9)
C7—C8—C9—O3	31.40 (10)	O3—C9—C12—C13	−125.97 (7)
C3—C8—C9—C1	−26.43 (10)	C8—C9—C12—C13	−10.95 (10)
C7—C8—C9—C1	157.12 (8)	C1—C9—C12—C13	122.33 (8)
C3—C8—C9—C12	106.23 (8)	O3—C9—C12—C10	−3.26 (5)
C7—C8—C9—C12	−70.21 (10)	C8—C9—C12—C10	111.76 (7)
O1—C1—C9—O3	−23.47 (11)	C1—C9—C12—C10	−114.96 (7)
N1—C1—C9—O3	160.56 (7)	N2—C12—C13—C14	61.23 (9)
O1—C1—C9—C8	−150.42 (8)	C10—C12—C13—C14	−174.06 (7)
N1—C1—C9—C8	33.61 (10)	C9—C12—C13—C14	−73.40 (9)
O1—C1—C9—C12	75.15 (10)	N2—C12—C13—C15	−61.98 (9)
N1—C1—C9—C12	−100.83 (8)	C10—C12—C13—C15	62.73 (10)
C17—O5—C10—O3	54.68 (9)	C9—C12—C13—C15	163.39 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ⁱ	0.93	2.59	3.3754 (12)	143
C15—H15A···O5	0.96	2.56	3.2151 (12)	126
C18—H18A···O1ⁱⁱ	0.96	2.58	3.4298 (13)	148
C18—H18C···O2ⁱⁱⁱ	0.96	2.58	3.3641 (12)	139

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₅
M_r	344.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.5721 (2), 10.4260 (2), 15.7633 (3)
β (°)	101.641 (1)
V (Å³)	1701.77 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.51 × 0.37 × 0.35

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.951, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	23124, 6242, 5286
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.760

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.108, 1.02
No. of reflections	6242
No. of parameters	231
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ⁱ	0.93	2.59	3.3754 (12)	143
C15—H15A···O5	0.96	2.56	3.2151 (12)	126
C18—H18A···O1ⁱⁱ	0.96	2.58	3.4298 (13)	148
C18—H18C···O2ⁱⁱⁱ	0.96	2.58	3.3641 (12)	139

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). Financial support from the National Science Foundation of China (20972067) is also acknowledged.

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