Methyl 4′-isobutyl-2,2′-dimethyl-1,3-dioxo-2,3-dihydro-1H,4′H-spiro­[iso­quinoline-4,5′-oxazole]-4′-carboxyl­ate

Fun, H.-K.; Quah, C.K.; Xu, K.; Zhang, Y.

doi:10.1107/S1600536811019003

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1519-o1520

doi:10.1107/S1600536811019003

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Methyl 4′-isobutyl-2,2′-dimethyl-1,3-dioxo-2,3-dihydro-1H,4′H-spiro[isoquinoline-4,5′-oxazole]-4′-carboxylate

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Kai Xu ^b and Yan Zhang ^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 10 May 2011; accepted 19 May 2011; online 25 May 2011)

In the isoquinoline ring system of the title molecule, C₁₉H₂₂N₂O₅, the N-heterocyclic ring is in a half-boat conformation. The dioxa-2-azaspiro ring is essentially planar [maximum deviation = 0.042 (1) Å] and forms a dihedral angle of 81.85 (4)° with the benzene ring. In the crystal, the molecules are linked via intermolecular C—H⋯O hydrogen bonds into chains along [010].

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 ); Mitchell et al. (1995 , 2000 ); Badillo et al. (2010 ); Wang et al. (2010 ); Nair et al. (2002 ); 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 ring conformations, see: Cremer & Pople (1975 ). For related structures, see: Fun et al. (2011a ,b ,c ,d ).

Experimental

Crystal data

C₁₉H₂₂N₂O₅
M_r = 358.39
Triclinic, $[P \overline 1]$
a = 8.6764 (1) Å
b = 8.9366 (1) Å
c = 12.0684 (2) Å
α = 93.495 (1)°
β = 109.892 (1)°
γ = 98.426 (1)°
V = 864.22 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.40 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.961, T_max = 0.982
25638 measured reflections
6231 independent reflections
5381 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.113
S = 1.05
6231 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4ⁱ	0.93	2.56	3.4353 (11)	158
C4—H4A⋯O2ⁱⁱ	0.93	2.56	3.2878 (11)	136
C12—H12C⋯O4ⁱ	0.96	2.59	3.3600 (11)	138
Symmetry codes: (i) -x+2, -y, -z; (ii) x, y-1, 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/S1600536811019003/rz2597sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019003/rz2597Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019003/rz2597Isup3.cml

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 and its derivatives have been reported to be redox mediators of photosystems I 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. Spirooxazoles have emerged as attractive synthetic targets because of their potent bioactivity (Badillo et al., 2011; Wang et al.; 2010; Nair et al., 2002). The title compound, which was derived from isoquinoline-1,3,4-trione and oxazoles (Huang et al., 2011), may has a potential use in biochemical and pharmaceutical fields. Due to the importance of the isoquinoline-1,3,4-trione derivatives, we report in this paper the crystal structure of the title compound with a relative configuration of (4S^*, 4'S^*).

In the title racemic compound, Fig. 1, atoms C9 and C10 are the stereo centers. The isoquinoline ring system (N1/C1-C9) is not completely planar, the N-heterocyclic ring (N1/C1/C6-C9) being distorted towards a half-boat conformation with atom C9 deviating by 0.167 (1) Å from the mean plane through the remaining atoms, puckering parameters (Cremer & Pople, 1975) Q = 0.2505 (9) Å, Θ = 114.3 (2)° and ϕ = 73.8 (2)°. The dioxa-2-azaspiro ring (N2/O3/C9-C11) is essentially planar [maximum deviation of 0.042 (1) Å at atoms C9 and C10] and it inclines at a dihedral angle of 81.85 (4)° with the benzene ring (C1-C6). Bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to related structures (Fun et al., 2011a,b,c,d).

In the crystal packing (Fig. 2), the molecules are linked via intermolecular C2–H2A···O4, C12–H12C···O4 and C4–H4A···O2 hydrogen bonds (Table 1) into one-dimensional chains along [010].

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); Mitchell et al. (1995, 2000); Badillo et al. (2010); Wang et al. (2010); Nair et al. (2002); 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 ring conformations, see: Cremer & Pople (1975). For related structures, see: Fun et al. (2011a,b,c,d).

Experimental top

The title compound was the main product from the acid-catalyzed transformation of the photocycloadduct of isoquinoline-1,3,4-trione and 4-isobutyl-5-methoxy-2-methyloxazole. The compound was purified by flash column chromatography with ethyl acetate/petroleum ether (1:4 v/v) as eluents. X-ray quality crystals of the title compound were obtained from slow evaporation of an acetone/petroleum ether solution (1:5 v/v). M.p. 421-423 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.
	Fig. 2. The crystal structure of the title compound, viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

Methyl 4'-isobutyl-2,2'-dimethyl-1,3-dioxo-2,3-dihydro-1H,4'H- spiro[isoquinoline-4,5'-oxazole]-4'-carboxylate top

Crystal data top

C₁₉H₂₂N₂O₅	Z = 2
M_r = 358.39	F(000) = 380
Triclinic, P1	D_x = 1.377 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6764 (1) Å	Cell parameters from 9993 reflections
b = 8.9366 (1) Å	θ = 2.3–35.1°
c = 12.0684 (2) Å	µ = 0.10 mm⁻¹
α = 93.495 (1)°	T = 100 K
β = 109.892 (1)°	Block, colourless
γ = 98.426 (1)°	0.40 × 0.29 × 0.18 mm
V = 864.22 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6231 independent reflections
Radiation source: fine-focus sealed tube	5381 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 32.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.961, T_max = 0.982	k = −13→13
25638 measured reflections	l = −16→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0637P)² + 0.1577P] where P = (F_o² + 2F_c²)/3
6231 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₉H₂₂N₂O₅	γ = 98.426 (1)°
M_r = 358.39	V = 864.22 (2) Å³
Triclinic, P1	Z = 2
a = 8.6764 (1) Å	Mo Kα radiation
b = 8.9366 (1) Å	µ = 0.10 mm⁻¹
c = 12.0684 (2) Å	T = 100 K
α = 93.495 (1)°	0.40 × 0.29 × 0.18 mm
β = 109.892 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6231 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5381 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.982	R_int = 0.027
25638 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.05	Δρ_max = 0.46 e Å⁻³
6231 reflections	Δρ_min = −0.24 e Å⁻³
240 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	0.56369 (10)	−0.13923 (8)	0.36689 (7)	0.02808 (16)
O2	0.61673 (8)	0.30662 (7)	0.21139 (6)	0.01906 (13)
O3	0.70178 (7)	0.17637 (7)	0.03819 (5)	0.01584 (12)
O4	1.13223 (8)	0.01941 (7)	0.19476 (6)	0.02001 (13)
O5	1.02241 (8)	0.00373 (7)	0.33903 (6)	0.01843 (13)
N1	0.60176 (9)	0.08767 (8)	0.29574 (6)	0.01547 (13)
N2	0.98015 (8)	0.26379 (8)	0.11623 (6)	0.01398 (13)
C1	0.71382 (9)	−0.05589 (9)	0.12763 (7)	0.01375 (14)
C2	0.75196 (10)	−0.12948 (9)	0.03755 (7)	0.01669 (15)
H2A	0.7913	−0.0729	−0.0126	0.020*
C3	0.73110 (11)	−0.28759 (10)	0.02283 (8)	0.01903 (16)
H3A	0.7556	−0.3364	−0.0378	0.023*
C4	0.67396 (11)	−0.37359 (10)	0.09800 (8)	0.01860 (16)
H4A	0.6621	−0.4792	0.0884	0.022*
C5	0.63485 (10)	−0.30090 (9)	0.18736 (7)	0.01695 (15)
H5A	0.5961	−0.3578	0.2376	0.020*
C6	0.65376 (10)	−0.14210 (9)	0.20173 (7)	0.01444 (14)
C7	0.60524 (10)	−0.06867 (10)	0.29540 (7)	0.01696 (15)
C8	0.64684 (9)	0.17845 (9)	0.21858 (7)	0.01427 (14)
C9	0.74719 (9)	0.11548 (9)	0.15004 (7)	0.01297 (13)
C10	0.94372 (9)	0.18962 (9)	0.21130 (7)	0.01221 (13)
C11	0.84438 (10)	0.25402 (9)	0.02944 (7)	0.01396 (14)
C12	0.81958 (11)	0.31809 (10)	−0.08488 (7)	0.01760 (15)
H12A	0.9226	0.3774	−0.0823	0.026*
H12B	0.7366	0.3818	−0.0976	0.026*
H12C	0.7834	0.2365	−0.1486	0.026*
C13	0.98781 (9)	0.30600 (9)	0.32243 (7)	0.01391 (14)
H13A	0.9391	0.3950	0.2979	0.017*
H13B	0.9362	0.2612	0.3753	0.017*
C14	1.17540 (9)	0.35881 (9)	0.39278 (7)	0.01424 (14)
H14A	1.2278	0.2682	0.4053	0.017*
C15	1.19883 (11)	0.43954 (11)	0.51412 (8)	0.02220 (17)
H15A	1.3156	0.4677	0.5597	0.033*
H15B	1.1464	0.3723	0.5551	0.033*
H15C	1.1492	0.5293	0.5039	0.033*
C16	1.26352 (11)	0.46363 (11)	0.32908 (8)	0.02157 (17)
H16A	1.3776	0.4980	0.3794	0.032*
H16B	1.2091	0.5499	0.3110	0.032*
H16C	1.2593	0.4089	0.2568	0.032*
C17	1.04488 (9)	0.06210 (9)	0.24456 (7)	0.01415 (14)
C18	1.10003 (13)	−0.12653 (12)	0.37361 (10)	0.0282 (2)
H18A	1.0943	−0.1492	0.4490	0.042*
H18B	1.2145	−0.1044	0.3798	0.042*
H18C	1.0429	−0.2127	0.3151	0.042*
C19	0.52591 (11)	0.15905 (10)	0.37250 (8)	0.02020 (16)
H19A	0.6016	0.2477	0.4198	0.030*
H19B	0.5024	0.0878	0.4235	0.030*
H19C	0.4243	0.1883	0.3243	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0440 (4)	0.0228 (3)	0.0276 (4)	0.0051 (3)	0.0250 (3)	0.0085 (3)
O2	0.0179 (3)	0.0170 (3)	0.0230 (3)	0.0048 (2)	0.0072 (2)	0.0034 (2)
O3	0.0145 (2)	0.0189 (3)	0.0129 (2)	0.0007 (2)	0.0035 (2)	0.0058 (2)
O4	0.0199 (3)	0.0196 (3)	0.0222 (3)	0.0068 (2)	0.0083 (2)	0.0017 (2)
O5	0.0200 (3)	0.0176 (3)	0.0172 (3)	0.0030 (2)	0.0053 (2)	0.0072 (2)
N1	0.0155 (3)	0.0164 (3)	0.0166 (3)	0.0018 (2)	0.0087 (2)	0.0016 (2)
N2	0.0163 (3)	0.0142 (3)	0.0129 (3)	0.0018 (2)	0.0071 (2)	0.0031 (2)
C1	0.0132 (3)	0.0142 (3)	0.0124 (3)	0.0001 (2)	0.0037 (2)	0.0014 (2)
C2	0.0182 (3)	0.0171 (3)	0.0141 (3)	−0.0007 (3)	0.0067 (3)	0.0000 (3)
C3	0.0200 (4)	0.0180 (4)	0.0177 (4)	0.0003 (3)	0.0070 (3)	−0.0026 (3)
C4	0.0186 (4)	0.0141 (3)	0.0204 (4)	0.0007 (3)	0.0047 (3)	0.0002 (3)
C5	0.0171 (3)	0.0153 (3)	0.0170 (3)	0.0005 (3)	0.0048 (3)	0.0039 (3)
C6	0.0141 (3)	0.0152 (3)	0.0133 (3)	0.0007 (3)	0.0045 (3)	0.0021 (3)
C7	0.0185 (3)	0.0176 (4)	0.0161 (3)	0.0015 (3)	0.0083 (3)	0.0031 (3)
C8	0.0115 (3)	0.0163 (3)	0.0144 (3)	0.0009 (2)	0.0044 (2)	0.0022 (3)
C9	0.0130 (3)	0.0140 (3)	0.0115 (3)	0.0010 (2)	0.0042 (2)	0.0030 (2)
C10	0.0122 (3)	0.0130 (3)	0.0117 (3)	0.0016 (2)	0.0048 (2)	0.0021 (2)
C11	0.0173 (3)	0.0121 (3)	0.0136 (3)	0.0020 (3)	0.0071 (3)	0.0022 (2)
C12	0.0227 (4)	0.0172 (3)	0.0137 (3)	0.0033 (3)	0.0070 (3)	0.0048 (3)
C13	0.0127 (3)	0.0157 (3)	0.0129 (3)	0.0015 (2)	0.0048 (2)	−0.0007 (3)
C14	0.0126 (3)	0.0153 (3)	0.0140 (3)	0.0012 (2)	0.0044 (2)	0.0002 (3)
C15	0.0170 (4)	0.0295 (4)	0.0163 (4)	−0.0015 (3)	0.0046 (3)	−0.0045 (3)
C16	0.0175 (4)	0.0252 (4)	0.0199 (4)	−0.0029 (3)	0.0065 (3)	0.0034 (3)
C17	0.0137 (3)	0.0130 (3)	0.0135 (3)	0.0005 (2)	0.0028 (3)	0.0014 (2)
C18	0.0264 (4)	0.0233 (4)	0.0332 (5)	0.0066 (4)	0.0054 (4)	0.0157 (4)
C19	0.0194 (4)	0.0222 (4)	0.0224 (4)	0.0029 (3)	0.0126 (3)	−0.0004 (3)

Geometric parameters (Å, º) top

O1—C7	1.2178 (10)	C9—C10	1.6262 (11)
O2—C8	1.2133 (10)	C10—C17	1.5295 (11)
O3—C11	1.3675 (10)	C10—C13	1.5462 (11)
O3—C9	1.4365 (9)	C11—C12	1.4859 (11)
O4—C17	1.2033 (10)	C12—H12A	0.9600
O5—C17	1.3431 (10)	C12—H12B	0.9600
O5—C18	1.4424 (11)	C12—H12C	0.9600
N1—C8	1.3875 (10)	C13—C14	1.5422 (11)
N1—C7	1.4016 (11)	C13—H13A	0.9700
N1—C19	1.4711 (11)	C13—H13B	0.9700
N2—C11	1.2694 (10)	C14—C16	1.5268 (12)
N2—C10	1.4608 (10)	C14—C15	1.5270 (12)
C1—C2	1.3948 (11)	C14—H14A	0.9800
C1—C6	1.3958 (11)	C15—H15A	0.9600
C1—C9	1.5062 (11)	C15—H15B	0.9600
C2—C3	1.3904 (12)	C15—H15C	0.9600
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.3925 (12)	C16—H16B	0.9600
C3—H3A	0.9300	C16—H16C	0.9600
C4—C5	1.3886 (12)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.3976 (11)	C18—H18C	0.9600
C5—H5A	0.9300	C19—H19A	0.9600
C6—C7	1.4833 (12)	C19—H19B	0.9600
C8—C9	1.5284 (11)	C19—H19C	0.9600

C11—O3—C9	107.44 (6)	C11—C12—H12A	109.5
C17—O5—C18	115.39 (7)	C11—C12—H12B	109.5
C8—N1—C7	124.82 (7)	H12A—C12—H12B	109.5
C8—N1—C19	116.23 (7)	C11—C12—H12C	109.5
C7—N1—C19	118.50 (7)	H12A—C12—H12C	109.5
C11—N2—C10	108.20 (6)	H12B—C12—H12C	109.5
C2—C1—C6	119.53 (7)	C14—C13—C10	115.65 (6)
C2—C1—C9	120.39 (7)	C14—C13—H13A	108.4
C6—C1—C9	119.97 (7)	C10—C13—H13A	108.4
C3—C2—C1	119.87 (8)	C14—C13—H13B	108.4
C3—C2—H2A	120.1	C10—C13—H13B	108.4
C1—C2—H2A	120.1	H13A—C13—H13B	107.4
C2—C3—C4	120.66 (8)	C16—C14—C15	109.57 (7)
C2—C3—H3A	119.7	C16—C14—C13	113.42 (7)
C4—C3—H3A	119.7	C15—C14—C13	109.33 (7)
C5—C4—C3	119.68 (8)	C16—C14—H14A	108.1
C5—C4—H4A	120.2	C15—C14—H14A	108.1
C3—C4—H4A	120.2	C13—C14—H14A	108.1
C4—C5—C6	119.92 (8)	C14—C15—H15A	109.5
C4—C5—H5A	120.0	C14—C15—H15B	109.5
C6—C5—H5A	120.0	H15A—C15—H15B	109.5
C1—C6—C5	120.33 (8)	C14—C15—H15C	109.5
C1—C6—C7	121.22 (7)	H15A—C15—H15C	109.5
C5—C6—C7	118.43 (7)	H15B—C15—H15C	109.5
O1—C7—N1	120.23 (8)	C14—C16—H16A	109.5
O1—C7—C6	122.86 (8)	C14—C16—H16B	109.5
N1—C7—C6	116.85 (7)	H16A—C16—H16B	109.5
O2—C8—N1	121.17 (8)	C14—C16—H16C	109.5
O2—C8—C9	121.21 (7)	H16A—C16—H16C	109.5
N1—C8—C9	117.46 (7)	H16B—C16—H16C	109.5
O3—C9—C1	109.04 (6)	O4—C17—O5	124.41 (7)
O3—C9—C8	106.82 (6)	O4—C17—C10	125.85 (7)
C1—C9—C8	113.48 (6)	O5—C17—C10	109.73 (7)
O3—C9—C10	102.23 (6)	O5—C18—H18A	109.5
C1—C9—C10	113.79 (6)	O5—C18—H18B	109.5
C8—C9—C10	110.63 (6)	H18A—C18—H18B	109.5
N2—C10—C17	110.09 (6)	O5—C18—H18C	109.5
N2—C10—C13	110.48 (6)	H18A—C18—H18C	109.5
C17—C10—C13	108.90 (6)	H18B—C18—H18C	109.5
N2—C10—C9	103.04 (6)	N1—C19—H19A	109.5
C17—C10—C9	109.24 (6)	N1—C19—H19B	109.5
C13—C10—C9	114.95 (6)	H19A—C19—H19B	109.5
N2—C11—O3	118.54 (7)	N1—C19—H19C	109.5
N2—C11—C12	127.35 (7)	H19A—C19—H19C	109.5
O3—C11—C12	114.11 (7)	H19B—C19—H19C	109.5

C6—C1—C2—C3	−0.47 (12)	O2—C8—C9—C1	−156.00 (7)
C9—C1—C2—C3	175.68 (7)	N1—C8—C9—C1	28.49 (9)
C1—C2—C3—C4	−0.65 (13)	O2—C8—C9—C10	74.70 (9)
C2—C3—C4—C5	1.05 (13)	N1—C8—C9—C10	−100.81 (8)
C3—C4—C5—C6	−0.31 (12)	C11—N2—C10—C17	122.44 (7)
C2—C1—C6—C5	1.20 (12)	C11—N2—C10—C13	−117.25 (7)
C9—C1—C6—C5	−174.97 (7)	C11—N2—C10—C9	6.03 (8)
C2—C1—C6—C7	−177.48 (7)	O3—C9—C10—N2	−7.21 (7)
C9—C1—C6—C7	6.35 (11)	C1—C9—C10—N2	110.20 (7)
C4—C5—C6—C1	−0.81 (12)	C8—C9—C10—N2	−120.67 (7)
C4—C5—C6—C7	177.91 (7)	O3—C9—C10—C17	−124.22 (6)
C8—N1—C7—O1	179.82 (8)	C1—C9—C10—C17	−6.82 (9)
C19—N1—C7—O1	−8.22 (12)	C8—C9—C10—C17	122.32 (7)
C8—N1—C7—C6	−2.85 (12)	O3—C9—C10—C13	113.04 (7)
C19—N1—C7—C6	169.11 (7)	C1—C9—C10—C13	−129.55 (7)
C1—C6—C7—O1	−174.64 (8)	C8—C9—C10—C13	−0.41 (9)
C5—C6—C7—O1	6.66 (13)	C10—N2—C11—O3	−2.63 (10)
C1—C6—C7—N1	8.11 (11)	C10—N2—C11—C12	177.58 (8)
C5—C6—C7—N1	−170.60 (7)	C9—O3—C11—N2	−2.67 (10)
C7—N1—C8—O2	168.43 (8)	C9—O3—C11—C12	177.15 (7)
C19—N1—C8—O2	−3.69 (11)	N2—C10—C13—C14	−72.97 (8)
C7—N1—C8—C9	−16.05 (11)	C17—C10—C13—C14	48.05 (9)
C19—N1—C8—C9	171.82 (7)	C9—C10—C13—C14	170.96 (6)
C11—O3—C9—C1	−114.79 (7)	C10—C13—C14—C16	71.60 (9)
C11—O3—C9—C8	122.21 (7)	C10—C13—C14—C15	−165.79 (7)
C11—O3—C9—C10	5.96 (8)	C18—O5—C17—O4	−5.16 (12)
C2—C1—C9—O3	40.97 (9)	C18—O5—C17—C10	174.99 (7)
C6—C1—C9—O3	−142.90 (7)	N2—C10—C17—O4	−5.43 (11)
C2—C1—C9—C8	159.89 (7)	C13—C10—C17—O4	−126.69 (8)
C6—C1—C9—C8	−23.97 (10)	C9—C10—C17—O4	107.03 (9)
C2—C1—C9—C10	−72.42 (9)	N2—C10—C17—O5	174.42 (6)
C6—C1—C9—C10	103.71 (8)	C13—C10—C17—O5	53.16 (8)
O2—C8—C9—O3	−35.81 (10)	C9—C10—C17—O5	−73.12 (8)
N1—C8—C9—O3	148.68 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	0.93	2.56	3.4353 (11)	158
C4—H4A···O2ⁱⁱ	0.93	2.56	3.2878 (11)	136
C12—H12C···O4ⁱ	0.96	2.59	3.3600 (11)	138

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂N₂O₅
M_r	358.39
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.6764 (1), 8.9366 (1), 12.0684 (2)
α, β, γ (°)	93.495 (1), 109.892 (1), 98.426 (1)
V (Å³)	864.22 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.29 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.961, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	25638, 6231, 5381
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.113, 1.05
No. of reflections	6231
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.24

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
C2—H2A···O4ⁱ	0.93	2.56	3.4353 (11)	158
C4—H4A···O2ⁱⁱ	0.93	2.56	3.2878 (11)	136
C12—H12C···O4ⁱ	0.96	2.59	3.3600 (11)	138

Symmetry codes: (i) −x+2, −y, −z; (ii) x, y−1, 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 Program for New Century Excellent Talents in Universities (NCET-08-0271) of China is also acknowledged.

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