1-Benzyl-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/S160053681101600X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1311-o1312

doi:10.1107/S160053681101600X

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1-Benzyl-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 21 April 2011; accepted 27 April 2011; online 7 May 2011)

In the isoquinoline ring system of the title molecule, C₂₂H₂₀N₂O₅, the N-heterocyclic ring is in a half-boat conformation. The dioxa-2-azaspiro ring is essentially planar [maximum deviation = 0.026 (1) Å] and forms dihedral angles of 22.53 (5) and 64.46 (5)° with the benzene and phenyl rings, respectively. The molecular structure is stabilized by a weak intramolecular C—H⋯O hydrogen bond, which generates an S(7) ring motif. In the crystal, molecules are linked via weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds into layers parallel to (102).

Related literature

For general background to and the potential biological activity of the title compound, see: Du et al. (2008 ); Chen et al. (2006 ); Yu et al. (2010 ); Harris et al. (2005 ); Zhang et al. (2004 ); 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 ring conformations, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Fun et al. (2011a ,b ).

Experimental

Crystal data

C₂₂H₂₀N₂O₅
M_r = 392.40
Monoclinic, P 2₁ /c
a = 9.7261 (2) Å
b = 12.4444 (2) Å
c = 15.8413 (3) Å
β = 108.884 (1)°
V = 1814.16 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.71 × 0.44 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.931, T_max = 0.975
21150 measured reflections
5368 independent reflections
4883 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.02
5368 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.51 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
C15—H15A⋯O5	0.93	2.51	3.3026 (12)	143
C20—H20C⋯O2ⁱ	0.96	2.49	3.4424 (13)	174
C21—H21B⋯N2ⁱⁱ	0.96	2.52	3.4018 (12)	152
C22—H22C⋯O2ⁱⁱ	0.96	2.50	3.3854 (12)	154
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S160053681101600X/lh5240sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101600X/lh5240Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681101600X/lh5240Isup3.cml

checkCIF report

Comment top

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). Compounds containing an oxazole moiety have been found to inhibit the activity of malignant tumors (Harris et al., 2005). Since many natural products especially the alkaloids containing isoquinoline or oxazole ring are bioactive, there has been intense interest in building frameworks containing isoquinoline moieties with an oxazole group (Yu et al., 2010; Zhang et al., 2004; Wang et al., 2010). The title compound was derived from photocycloaddition of isoquinoline-1,3,4-trione and oxazole (Huang et al., 2011). Since it may have a potential use in biochemical and pharmaceutical fields, we report in this paper 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 stereo 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 C9 deviating by 0.222 (1) Å from the mean plane through the remaining atoms, puckering parameters (Cremer & Pople, 1975) Q = 0.329 (1) Å, Θ = 62.51 (17)° and ϕ = 104.40 (18)°. The dioxa-2-azaspiro ring (N2/O4/C10-C12) is essentially planar [maximum deviation of 0.026 (1) Å at atoms O4 and C10] and it inclines at dihedral angles of 22.53 (5) and 64.46 (5)° with the benzene and phenyl rings (C3-C8 and C14-C19), respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to related structures (Fun et al., 2011a, b). The molecular structure is stabilized by a weak intramolecular C15–H15A···O5 hydrogen bond (Table 1) which generates a S(7) ring motif (Fig. 1, Bernstein et al., 1995).

In the crystal structure, Fig. 2, molecules are linked via intermolecular C20–H20C···O2ⁱ, C21–H21B···N2ⁱⁱ and C22–H22C···O2ⁱⁱ hydrogen bonds (see Table 1 for symmetry codes) into two-dimensional planes parallel to (102).

Related literature top

For general background to and the potential biological activity of the title compound, see: Du et al. (2008); Chen et al. (2006); Yu et al. (2010); Harris et al. (2005); Zhang et al. (2004); 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 ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Fun et al. (2011a,b).

Experimental top

The title compound was the main product from the photoreaction between isoquinoline-1,3,4-trione and 4-benzyl-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. 463-465 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. A weak intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

1-Benzyl-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

C₂₂H₂₀N₂O₅	F(000) = 824
M_r = 392.40	D_x = 1.437 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9898 reflections
a = 9.7261 (2) Å	θ = 2.7–30.2°
b = 12.4444 (2) Å	µ = 0.10 mm⁻¹
c = 15.8413 (3) Å	T = 100 K
β = 108.884 (1)°	Block, colourless
V = 1814.16 (6) Å³	0.71 × 0.44 × 0.25 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5368 independent reflections
Radiation source: fine-focus sealed tube	4883 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 30.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.931, T_max = 0.975	k = −17→17
21150 measured reflections	l = −15→22

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0545P)² + 0.7208P] where P = (F_o² + 2F_c²)/3
5368 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₂H₂₀N₂O₅	V = 1814.16 (6) Å³
M_r = 392.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7261 (2) Å	µ = 0.10 mm⁻¹
b = 12.4444 (2) Å	T = 100 K
c = 15.8413 (3) Å	0.71 × 0.44 × 0.25 mm
β = 108.884 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5368 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4883 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.975	R_int = 0.019
21150 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.02	Δρ_max = 0.51 e Å⁻³
5368 reflections	Δρ_min = −0.27 e Å⁻³
265 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	0.70635 (8)	0.71051 (6)	0.91416 (5)	0.01856 (15)
O2	0.90622 (8)	1.02544 (6)	0.87008 (5)	0.01959 (15)
O3	0.71792 (7)	0.61939 (5)	0.75908 (4)	0.01336 (13)
O4	0.46875 (7)	0.58791 (5)	0.73113 (4)	0.01357 (13)
O5	0.56352 (7)	0.57911 (5)	0.61557 (4)	0.01337 (13)
N1	0.78670 (8)	0.87467 (6)	0.88611 (5)	0.01347 (15)
N2	0.46589 (8)	0.77013 (6)	0.74800 (5)	0.01303 (15)
C1	0.74250 (9)	0.76872 (7)	0.86397 (6)	0.01282 (16)
C2	0.86611 (10)	0.93487 (7)	0.84373 (6)	0.01376 (16)
C3	0.90674 (9)	0.88137 (7)	0.77166 (6)	0.01332 (16)
C4	1.00910 (10)	0.93045 (8)	0.73946 (6)	0.01692 (18)
H4A	1.0434	0.9988	0.7590	0.020*
C5	1.05954 (10)	0.87726 (8)	0.67839 (7)	0.01917 (19)
H5A	1.1287	0.9094	0.6576	0.023*
C6	1.00631 (11)	0.77555 (8)	0.64832 (7)	0.01886 (19)
H6A	1.0416	0.7393	0.6083	0.023*
C7	0.90070 (10)	0.72769 (8)	0.67776 (6)	0.01571 (17)
H7A	0.8635	0.6607	0.6560	0.019*
C8	0.85086 (9)	0.78033 (7)	0.73984 (6)	0.01255 (16)
C9	0.73190 (9)	0.73502 (7)	0.76955 (6)	0.01148 (15)
C10	0.57599 (9)	0.62694 (7)	0.69477 (6)	0.01140 (16)
C11	0.41832 (10)	0.67863 (7)	0.76214 (6)	0.01311 (16)
C12	0.57073 (9)	0.75055 (7)	0.70176 (6)	0.01121 (15)
C13	0.55210 (10)	0.82504 (7)	0.62266 (6)	0.01359 (16)
H13A	0.5951	0.8941	0.6447	0.016*
H13B	0.6053	0.7954	0.5858	0.016*
C14	0.39571 (10)	0.84262 (7)	0.56521 (6)	0.01299 (16)
C15	0.30401 (10)	0.75654 (8)	0.52783 (6)	0.01561 (17)
H15A	0.3384	0.6865	0.5397	0.019*
C16	0.16165 (10)	0.77436 (8)	0.47305 (6)	0.01777 (18)
H16A	0.1016	0.7163	0.4488	0.021*
C17	0.10889 (10)	0.87872 (9)	0.45445 (6)	0.01908 (19)
H17A	0.0142	0.8906	0.4173	0.023*
C18	0.19865 (11)	0.96482 (8)	0.49175 (7)	0.01907 (19)
H18A	0.1639	1.0347	0.4798	0.023*
C19	0.34088 (10)	0.94687 (8)	0.54716 (6)	0.01628 (17)
H19A	0.3999	1.0051	0.5724	0.020*
C20	0.76802 (11)	0.92219 (8)	0.96661 (6)	0.01787 (18)
H20A	0.7099	0.8752	0.9893	0.027*
H20B	0.7205	0.9905	0.9520	0.027*
H20C	0.8614	0.9318	1.0111	0.027*
C21	0.60558 (10)	0.46687 (7)	0.62301 (6)	0.01648 (17)
H21A	0.5714	0.4339	0.5652	0.025*
H21B	0.5637	0.4310	0.6625	0.025*
H21C	0.7095	0.4615	0.6463	0.025*
C22	0.31256 (10)	0.65843 (8)	0.80979 (6)	0.01721 (18)
H22A	0.2786	0.7257	0.8251	0.026*
H22B	0.3587	0.6182	0.8632	0.026*
H22C	0.2318	0.6182	0.7720	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0235 (3)	0.0169 (3)	0.0153 (3)	−0.0026 (3)	0.0065 (3)	0.0021 (3)
O2	0.0232 (3)	0.0136 (3)	0.0192 (3)	−0.0043 (3)	0.0031 (3)	−0.0019 (3)
O3	0.0134 (3)	0.0090 (3)	0.0152 (3)	0.0000 (2)	0.0012 (2)	0.0001 (2)
O4	0.0156 (3)	0.0110 (3)	0.0158 (3)	−0.0014 (2)	0.0074 (2)	−0.0007 (2)
O5	0.0181 (3)	0.0099 (3)	0.0120 (3)	0.0012 (2)	0.0047 (2)	−0.0010 (2)
N1	0.0148 (3)	0.0127 (3)	0.0119 (3)	−0.0008 (3)	0.0030 (3)	−0.0011 (3)
N2	0.0123 (3)	0.0137 (3)	0.0127 (3)	0.0009 (3)	0.0035 (3)	−0.0012 (3)
C1	0.0118 (4)	0.0126 (4)	0.0122 (4)	0.0006 (3)	0.0013 (3)	0.0000 (3)
C2	0.0127 (4)	0.0129 (4)	0.0131 (4)	−0.0003 (3)	0.0004 (3)	0.0012 (3)
C3	0.0118 (4)	0.0133 (4)	0.0131 (4)	0.0000 (3)	0.0016 (3)	0.0015 (3)
C4	0.0141 (4)	0.0168 (4)	0.0180 (4)	−0.0023 (3)	0.0026 (3)	0.0034 (3)
C5	0.0149 (4)	0.0227 (5)	0.0204 (4)	0.0003 (3)	0.0064 (3)	0.0064 (4)
C6	0.0185 (4)	0.0211 (5)	0.0191 (4)	0.0040 (3)	0.0089 (4)	0.0034 (3)
C7	0.0163 (4)	0.0147 (4)	0.0162 (4)	0.0019 (3)	0.0053 (3)	0.0011 (3)
C8	0.0113 (4)	0.0127 (4)	0.0123 (4)	0.0008 (3)	0.0018 (3)	0.0019 (3)
C9	0.0125 (4)	0.0088 (3)	0.0120 (4)	−0.0001 (3)	0.0025 (3)	0.0002 (3)
C10	0.0121 (4)	0.0103 (3)	0.0114 (4)	−0.0003 (3)	0.0032 (3)	0.0002 (3)
C11	0.0134 (4)	0.0142 (4)	0.0110 (4)	0.0005 (3)	0.0029 (3)	−0.0016 (3)
C12	0.0115 (3)	0.0098 (3)	0.0114 (4)	−0.0001 (3)	0.0025 (3)	−0.0008 (3)
C13	0.0126 (4)	0.0121 (4)	0.0145 (4)	−0.0002 (3)	0.0023 (3)	0.0027 (3)
C14	0.0133 (4)	0.0137 (4)	0.0114 (4)	0.0007 (3)	0.0032 (3)	0.0012 (3)
C15	0.0160 (4)	0.0146 (4)	0.0154 (4)	−0.0001 (3)	0.0040 (3)	0.0004 (3)
C16	0.0148 (4)	0.0216 (5)	0.0160 (4)	−0.0033 (3)	0.0037 (3)	−0.0014 (3)
C17	0.0131 (4)	0.0270 (5)	0.0157 (4)	0.0030 (3)	0.0026 (3)	0.0014 (4)
C18	0.0181 (4)	0.0185 (4)	0.0188 (4)	0.0063 (3)	0.0035 (3)	0.0021 (3)
C19	0.0166 (4)	0.0140 (4)	0.0164 (4)	0.0011 (3)	0.0029 (3)	0.0002 (3)
C20	0.0207 (4)	0.0191 (4)	0.0135 (4)	−0.0005 (3)	0.0052 (3)	−0.0037 (3)
C21	0.0208 (4)	0.0107 (4)	0.0170 (4)	0.0020 (3)	0.0049 (3)	−0.0016 (3)
C22	0.0175 (4)	0.0196 (4)	0.0167 (4)	−0.0016 (3)	0.0085 (3)	−0.0009 (3)

Geometric parameters (Å, º) top

O1—C1	1.2089 (11)	C10—C12	1.5443 (12)
O2—C2	1.2212 (11)	C11—C22	1.4810 (12)
O3—C10	1.4290 (10)	C12—C13	1.5216 (12)
O3—C9	1.4498 (10)	C13—C14	1.5145 (12)
O4—C11	1.3829 (11)	C13—H13A	0.9700
O4—C10	1.4298 (10)	C13—H13B	0.9700
O5—C10	1.3581 (10)	C14—C19	1.3967 (12)
O5—C21	1.4495 (11)	C14—C15	1.3971 (13)
N1—C2	1.3942 (12)	C15—C16	1.3934 (13)
N1—C1	1.3959 (11)	C15—H15A	0.9300
N1—C20	1.4694 (12)	C16—C17	1.3924 (14)
N2—C11	1.2759 (12)	C16—H16A	0.9300
N2—C12	1.4557 (11)	C17—C18	1.3876 (15)
C1—C9	1.5244 (12)	C17—H17A	0.9300
C2—C3	1.4815 (13)	C18—C19	1.3957 (13)
C3—C4	1.3976 (12)	C18—H18A	0.9300
C3—C8	1.3975 (12)	C19—H19A	0.9300
C4—C5	1.3864 (14)	C20—H20A	0.9600
C4—H4A	0.9300	C20—H20B	0.9600
C5—C6	1.3919 (15)	C20—H20C	0.9600
C5—H5A	0.9300	C21—H21A	0.9600
C6—C7	1.3919 (13)	C21—H21B	0.9600
C6—H6A	0.9300	C21—H21C	0.9600
C7—C8	1.3928 (12)	C22—H22A	0.9600
C7—H7A	0.9300	C22—H22B	0.9600
C8—C9	1.4935 (12)	C22—H22C	0.9600
C9—C12	1.5995 (12)

C10—O3—C9	92.84 (6)	N2—C12—C10	104.34 (7)
C11—O4—C10	104.75 (7)	C13—C12—C10	123.07 (7)
C10—O5—C21	114.13 (7)	N2—C12—C9	112.11 (7)
C2—N1—C1	124.06 (8)	C13—C12—C9	117.14 (7)
C2—N1—C20	116.42 (8)	C10—C12—C9	83.10 (6)
C1—N1—C20	118.92 (8)	C14—C13—C12	114.31 (7)
C11—N2—C12	106.97 (7)	C14—C13—H13A	108.7
O1—C1—N1	122.16 (8)	C12—C13—H13A	108.7
O1—C1—C9	122.60 (8)	C14—C13—H13B	108.7
N1—C1—C9	115.08 (7)	C12—C13—H13B	108.7
O2—C2—N1	119.79 (8)	H13A—C13—H13B	107.6
O2—C2—C3	122.87 (8)	C19—C14—C15	118.45 (8)
N1—C2—C3	117.20 (8)	C19—C14—C13	119.99 (8)
C4—C3—C8	120.09 (8)	C15—C14—C13	121.55 (8)
C4—C3—C2	118.95 (8)	C16—C15—C14	120.75 (9)
C8—C3—C2	120.84 (8)	C16—C15—H15A	119.6
C5—C4—C3	120.06 (9)	C14—C15—H15A	119.6
C5—C4—H4A	120.0	C17—C16—C15	120.27 (9)
C3—C4—H4A	120.0	C17—C16—H16A	119.9
C4—C5—C6	119.77 (9)	C15—C16—H16A	119.9
C4—C5—H5A	120.1	C18—C17—C16	119.48 (9)
C6—C5—H5A	120.1	C18—C17—H17A	120.3
C5—C6—C7	120.50 (9)	C16—C17—H17A	120.3
C5—C6—H6A	119.7	C17—C18—C19	120.21 (9)
C7—C6—H6A	119.7	C17—C18—H18A	119.9
C6—C7—C8	119.90 (9)	C19—C18—H18A	119.9
C6—C7—H7A	120.0	C18—C19—C14	120.83 (9)
C8—C7—H7A	120.0	C18—C19—H19A	119.6
C7—C8—C3	119.62 (8)	C14—C19—H19A	119.6
C7—C8—C9	121.81 (8)	N1—C20—H20A	109.5
C3—C8—C9	118.46 (8)	N1—C20—H20B	109.5
O3—C9—C8	113.09 (7)	H20A—C20—H20B	109.5
O3—C9—C1	111.06 (7)	N1—C20—H20C	109.5
C8—C9—C1	113.09 (7)	H20A—C20—H20C	109.5
O3—C9—C12	90.45 (6)	H20B—C20—H20C	109.5
C8—C9—C12	115.70 (7)	O5—C21—H21A	109.5
C1—C9—C12	111.46 (7)	O5—C21—H21B	109.5
O5—C10—O3	113.99 (7)	H21A—C21—H21B	109.5
O5—C10—O4	111.38 (7)	O5—C21—H21C	109.5
O3—C10—O4	110.66 (7)	H21A—C21—H21C	109.5
O5—C10—C12	120.51 (7)	H21B—C21—H21C	109.5
O3—C10—C12	93.50 (6)	C11—C22—H22A	109.5
O4—C10—C12	105.31 (6)	C11—C22—H22B	109.5
N2—C11—O4	118.40 (8)	H22A—C22—H22B	109.5
N2—C11—C22	126.30 (8)	C11—C22—H22C	109.5
O4—C11—C22	115.29 (8)	H22A—C22—H22C	109.5
N2—C12—C13	113.35 (7)	H22B—C22—H22C	109.5

C2—N1—C1—O1	161.43 (9)	C9—O3—C10—C12	−2.69 (6)
C20—N1—C1—O1	−9.42 (13)	C11—O4—C10—O5	−136.88 (7)
C2—N1—C1—C9	−23.15 (12)	C11—O4—C10—O3	95.23 (8)
C20—N1—C1—C9	166.00 (8)	C11—O4—C10—C12	−4.62 (8)
C1—N1—C2—O2	−176.58 (8)	C12—N2—C11—O4	−1.64 (11)
C20—N1—C2—O2	−5.52 (13)	C12—N2—C11—C22	178.08 (8)
C1—N1—C2—C3	−0.79 (13)	C10—O4—C11—N2	4.24 (10)
C20—N1—C2—C3	170.27 (8)	C10—O4—C11—C22	−175.51 (7)
O2—C2—C3—C4	7.97 (14)	C11—N2—C12—C13	134.85 (8)
N1—C2—C3—C4	−167.68 (8)	C11—N2—C12—C10	−1.51 (9)
O2—C2—C3—C8	−175.94 (9)	C11—N2—C12—C9	−89.79 (8)
N1—C2—C3—C8	8.41 (13)	O5—C10—C12—N2	130.74 (8)
C8—C3—C4—C5	−2.44 (14)	O3—C10—C12—N2	−108.67 (7)
C2—C3—C4—C5	173.68 (9)	O4—C10—C12—N2	3.87 (9)
C3—C4—C5—C6	0.93 (14)	O5—C10—C12—C13	−0.15 (12)
C4—C5—C6—C7	1.28 (15)	O3—C10—C12—C13	120.45 (8)
C5—C6—C7—C8	−1.96 (14)	O4—C10—C12—C13	−127.02 (8)
C6—C7—C8—C3	0.44 (14)	O5—C10—C12—C9	−118.14 (8)
C6—C7—C8—C9	176.53 (8)	O3—C10—C12—C9	2.45 (6)
C4—C3—C8—C7	1.75 (13)	O4—C10—C12—C9	114.99 (7)
C2—C3—C8—C7	−174.30 (8)	O3—C9—C12—N2	100.30 (7)
C4—C3—C8—C9	−174.47 (8)	C8—C9—C12—N2	−143.66 (8)
C2—C3—C8—C9	9.48 (12)	C1—C9—C12—N2	−12.61 (10)
C10—O3—C9—C8	−115.75 (7)	O3—C9—C12—C13	−126.16 (8)
C10—O3—C9—C1	115.86 (7)	C8—C9—C12—C13	−10.12 (11)
C10—O3—C9—C12	2.59 (6)	C1—C9—C12—C13	120.93 (8)
C7—C8—C9—O3	24.17 (12)	O3—C9—C12—C10	−2.41 (6)
C3—C8—C9—O3	−159.69 (8)	C8—C9—C12—C10	113.63 (8)
C7—C8—C9—C1	151.50 (8)	C1—C9—C12—C10	−115.32 (7)
C3—C8—C9—C1	−32.36 (11)	N2—C12—C13—C14	−42.62 (10)
C7—C8—C9—C12	−78.22 (10)	C10—C12—C13—C14	84.47 (10)
C3—C8—C9—C12	97.91 (9)	C9—C12—C13—C14	−175.60 (7)
O1—C1—C9—O3	−17.55 (12)	C12—C13—C14—C19	126.06 (9)
N1—C1—C9—O3	167.04 (7)	C12—C13—C14—C15	−55.14 (11)
O1—C1—C9—C8	−145.95 (9)	C19—C14—C15—C16	0.68 (13)
N1—C1—C9—C8	38.65 (10)	C13—C14—C15—C16	−178.14 (8)
O1—C1—C9—C12	81.68 (11)	C14—C15—C16—C17	0.27 (14)
N1—C1—C9—C12	−93.73 (9)	C15—C16—C17—C18	−0.75 (14)
C21—O5—C10—O3	55.72 (9)	C16—C17—C18—C19	0.27 (14)
C21—O5—C10—O4	−70.36 (9)	C17—C18—C19—C14	0.70 (15)
C21—O5—C10—C12	165.60 (7)	C15—C14—C19—C18	−1.16 (14)
C9—O3—C10—O5	123.05 (7)	C13—C14—C19—C18	177.68 (8)
C9—O3—C10—O4	−110.49 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O5	0.93	2.51	3.3026 (12)	143
C20—H20C···O2ⁱ	0.96	2.49	3.4424 (13)	174
C21—H21B···N2ⁱⁱ	0.96	2.52	3.4018 (12)	152
C22—H22C···O2ⁱⁱ	0.96	2.50	3.3854 (12)	154

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N₂O₅
M_r	392.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.7261 (2), 12.4444 (2), 15.8413 (3)
β (°)	108.884 (1)
V (Å³)	1814.16 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.71 × 0.44 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.931, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	21150, 5368, 4883
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.02
No. of reflections	5368
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.27

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
C15—H15A···O5	0.93	2.51	3.3026 (12)	143
C20—H20C···O2ⁱ	0.96	2.49	3.4424 (13)	174
C21—H21B···N2ⁱⁱ	0.96	2.52	3.4018 (12)	152
C22—H22C···O2ⁱⁱ	0.96	2.50	3.3854 (12)	154

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

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 University (NCET-08-0271) of China is also acknowledged.

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