organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 5| May 2011| Pages o1273-o1274

(1S*,4′S*,5R*)-1-Iso­butyl-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

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 compound, C19H22N2O5, the N-heterocyclic ring is in a half-chair conformation. The dioxa-2-aza­spiro ring is essentially planar [maximum deviation of 0.025 (1) Å] and forms a dihedral angle of 23.51 (5)° with the benzene ring. In the crystal, mol­ecules are linked via weak inter­molecular C—H⋯O and C—H⋯N 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[Pollers-Wieers, C., Vekemans, J., Toppet, S. & Hoornaert, G. (1981). Tetrahedron, 37, 4321-4326.]); Malamas et al. (1994[Malamas, M. S., Hohman, T. C. & Millen, J. (1994). J. Med. Chem. 37, 2043-2058.]); Yu et al. (2010[Yu, H., Li, J., Kou, Z., Du, X., Wei, Y., Fun, H.-K., Xu, J. & Zhang, Y. (2010). J. Org. Chem. 75, 2989-3001.]); Du et al. (2008[Du, J.-Q., Wu, J., Zhang, H.-J., Zhang, Y.-H., Qiu, B.-Y., Wu, F., Chen, Y.-H., Li, J.-Y., Nan, F.-J., Ding, J.-P. & Li, J. (2008). Biol. Chem. 283, 30205-30215.]); Chen et al. (2006[Chen, Y.-H., Zhang, Y.-H., Zhang, H.-J., Liu, D.-Z., Gu, M., Li, J.-Y., Wu, F., Zhu, X.-Z., Li, J. & Nan, F.-J. (2006). J. Med. Chem. 49, 1613-1623.]); Zhang et al. (2006[Zhang, Y.-H., Zhang, H.-J., Wu, F., Chen, Y.-H., Ma, X.-Q., Du, J.-Q., Zhou, Z.-L., Li, J.-Y., Nan, F.-J. & Li, J. (2006). FEBS J. 273, 4842-4852.]); Mitchell et al. (1995[Mitchell, G., Clarke, E. D., Ridley, S. M., Greenhow, D. T., Gillen, K. J., Vohra, S. K. & Wardman, P. (1995). Pestic. Sci. 44, 49-58.], 2000[Mitchell, G., Clarke, E. D., Ridley, S. M., Bartlett, D. W., Gillen, K. J., Vohra, S. K., Greenhow, D. T., Ormrod, J. C. & Wardman, P. (2000). Pest. Manag. Sci. 56, 120-126.]); Harris et al. (2005[Harris, P. A., Cheung, M., Hunter, R. N., Brown, M. L., Veal, J. M., Nolte, R. T., Wang, L., Liu, W., Crosby, R. M., Johnson, J. H., Epperly, A. H., Kumar, R., Luttrell, D. K. & Stafford, J. A. (2005). J. Med. Chem. 48, 1610-1619.]); Wang et al. (2010[Wang, L., Huang, Y. C., Liu, Y., Fun, H.-K., Zhang, Y. & Xu, J. H. (2010). J. Org. Chem. 75, 7757-7768.]); Huang et al. (2011[Huang, C., Yu, H., Miao, Z., Zhou, J., Wang, S., Fun, H.-K., Xu, J. & Zhang, Y. (2011). Org. Biomol. Chem. 9, 3629-3631.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For a related structure, see: Fun et al. (2011[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011). Acta Cryst. E67, o1271-o1272.]).

[Scheme 1]

Experimental

Crystal data
  • C19H22N2O5

  • Mr = 358.39

  • Monoclinic, P 21 /c

  • a = 8.0488 (1) Å

  • b = 13.6065 (2) Å

  • c = 16.7880 (2) Å

  • β = 106.298 (1)°

  • V = 1764.67 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.25 × 0.16 × 0.12 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.988

  • 24267 measured reflections

  • 5139 independent reflections

  • 4476 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.103

  • S = 1.03

  • 5139 reflections

  • 240 parameters

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C16—H16B⋯O5i 0.96 2.57 3.4213 (14) 148
C17—H17C⋯N2ii 0.96 2.59 3.5119 (14) 162
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Oxazole rings are found in some bioactive natural products such as Annuloline and Ostreogrycin A. Compounds with oxazole moiety have been found to have inhibition activity on malignant tumors (Harris et al., 2005). Additionally, many natural products especially the alkaloids containing the isoquinoline or oxazole ring are bioactive. As such there has been intense development of methodology to construct such moieties (Wang et al., 2010). 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 kind 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 I and have been used as herbicides (Mitchell et al., 2000; 1995). 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. 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-chair conformation with atoms N1/C2/C3/C8 forming the best least-squares plane and and atoms C1 and C9 are 0.2278 (8) and -0.3215 (8)Å, respectively, from this plane. The puckering parameters (Cremer & Pople, 1975) are Q = 0.3656 (10)) Å, Θ = 114.98 (16)° and ϕ =274.96 (16)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to a related structure (Fun et al., 2011). The dioxa-2-azaspiro ring (N2/O4/C10-C12) is essentially planar [maximum deviation of 0.025 (1) Å at atom O4] and is inclined at a dihedral angle of 23.51 (5)° with the benzene ring (C3-C8).

In the crystal (Fig. 2), molecules are linked via weak intermolecular C16–H16B···O5i and C17–H17C···N2ii hydrogen bonds (see Table 1 for symmetry codes) 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); 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 ring conformations, see: Cremer & Pople (1975). For a related structure, see: Fun et al. (2011).

Experimental top

The title compound was the main product from the photoreaction between 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) as eluents. X-ray quality crystals of the title compound was obtained from slow evaporation of an acetone and petroleum ether solution of the title compund (1:5) (m.p. 421-423 K).

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C–H = 0.93 - 0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl groups.

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
[Figure 1] Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Part of 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-Isobutyl-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
C19H22N2O5F(000) = 760
Mr = 358.39Dx = 1.349 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9893 reflections
a = 8.0488 (1) Åθ = 3.0–35.8°
b = 13.6065 (2) ŵ = 0.10 mm1
c = 16.7880 (2) ÅT = 100 K
β = 106.298 (1)°Block, colourless
V = 1764.67 (4) Å30.25 × 0.16 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5139 independent reflections
Radiation source: fine-focus sealed tube4476 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1111
Tmin = 0.976, Tmax = 0.988k = 1919
24267 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0553P)2 + 0.5274P]
where P = (Fo2 + 2Fc2)/3
5139 reflections(Δ/σ)max = 0.001
240 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C19H22N2O5V = 1764.67 (4) Å3
Mr = 358.39Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.0488 (1) ŵ = 0.10 mm1
b = 13.6065 (2) ÅT = 100 K
c = 16.7880 (2) Å0.25 × 0.16 × 0.12 mm
β = 106.298 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5139 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
4476 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.988Rint = 0.025
24267 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.03Δρmax = 0.44 e Å3
5139 reflectionsΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
O10.79496 (9)0.57309 (5)0.66503 (5)0.02050 (15)
O21.34091 (9)0.52679 (5)0.64902 (5)0.02368 (16)
O30.82385 (8)0.77489 (5)0.67549 (4)0.01707 (14)
O40.57984 (8)0.76986 (5)0.55910 (4)0.01918 (15)
O50.74064 (9)0.91191 (5)0.58917 (5)0.02068 (15)
N11.05809 (10)0.55116 (6)0.64124 (5)0.01658 (16)
N20.75988 (10)0.67859 (6)0.50490 (5)0.01618 (16)
C10.92559 (11)0.60875 (7)0.65547 (5)0.01528 (17)
C21.22975 (11)0.58267 (7)0.65818 (6)0.01617 (17)
C31.26757 (11)0.68377 (7)0.69139 (6)0.01539 (17)
C41.44041 (12)0.71107 (7)0.72596 (6)0.01982 (19)
H4A1.52920.66750.72550.024*
C51.47831 (12)0.80359 (8)0.76086 (6)0.0219 (2)
H5A1.59270.82120.78590.026*
C61.34573 (13)0.87042 (7)0.75865 (6)0.01974 (19)
H6A1.37220.93270.78150.024*
C71.17372 (12)0.84428 (7)0.72237 (6)0.01706 (17)
H7A1.08570.88950.71980.020*
C81.13408 (11)0.75022 (7)0.68989 (5)0.01429 (16)
C90.95168 (11)0.71880 (6)0.64877 (5)0.01391 (16)
C100.74669 (11)0.81247 (7)0.59376 (6)0.01633 (17)
C110.60784 (12)0.69179 (7)0.51199 (6)0.01745 (18)
C120.86979 (11)0.75430 (7)0.55523 (5)0.01432 (16)
C130.99210 (11)0.80256 (7)0.51287 (6)0.01624 (17)
H13A1.09110.75970.51870.019*
H13B1.03430.86320.54190.019*
C140.91552 (13)0.82618 (7)0.42050 (6)0.01925 (18)
H14A0.86910.76540.39140.023*
C150.76970 (14)0.90189 (8)0.40468 (7)0.0259 (2)
H15A0.67400.87510.42110.039*
H15B0.73280.91790.34670.039*
H15C0.81060.96020.43630.039*
C161.06068 (15)0.86338 (9)0.38598 (7)0.0274 (2)
H16A1.14850.81380.39320.041*
H16B1.11010.92190.41510.041*
H16C1.01460.87780.32800.041*
C171.02112 (14)0.44773 (7)0.61770 (7)0.0245 (2)
H17A0.90020.44030.58980.037*
H17B1.05090.40750.66660.037*
H17C1.08810.42790.58130.037*
C180.62742 (16)0.95764 (8)0.63135 (9)0.0323 (3)
H18A0.62491.02730.62200.048*
H18B0.66930.94470.68980.048*
H18C0.51270.93140.61030.048*
C190.45239 (12)0.63113 (8)0.47491 (7)0.0226 (2)
H19A0.48050.58120.44040.034*
H19B0.36180.67210.44210.034*
H19C0.41430.60070.51830.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0177 (3)0.0217 (3)0.0236 (3)0.0037 (3)0.0082 (3)0.0008 (3)
O20.0187 (3)0.0198 (3)0.0330 (4)0.0042 (3)0.0081 (3)0.0012 (3)
O30.0149 (3)0.0201 (3)0.0172 (3)0.0031 (2)0.0062 (2)0.0021 (2)
O40.0126 (3)0.0210 (3)0.0236 (4)0.0003 (2)0.0045 (2)0.0023 (3)
O50.0209 (3)0.0146 (3)0.0297 (4)0.0029 (2)0.0123 (3)0.0011 (3)
N10.0156 (3)0.0137 (3)0.0207 (4)0.0006 (3)0.0056 (3)0.0008 (3)
N20.0156 (3)0.0163 (4)0.0151 (4)0.0011 (3)0.0018 (3)0.0005 (3)
C10.0155 (4)0.0165 (4)0.0135 (4)0.0004 (3)0.0034 (3)0.0001 (3)
C20.0151 (4)0.0166 (4)0.0164 (4)0.0010 (3)0.0039 (3)0.0021 (3)
C30.0144 (4)0.0166 (4)0.0149 (4)0.0001 (3)0.0036 (3)0.0008 (3)
C40.0145 (4)0.0223 (5)0.0213 (4)0.0010 (3)0.0027 (3)0.0022 (4)
C50.0163 (4)0.0247 (5)0.0218 (5)0.0041 (3)0.0005 (3)0.0009 (4)
C60.0220 (4)0.0196 (4)0.0166 (4)0.0048 (3)0.0037 (3)0.0022 (3)
C70.0180 (4)0.0176 (4)0.0159 (4)0.0002 (3)0.0054 (3)0.0013 (3)
C80.0138 (4)0.0167 (4)0.0125 (4)0.0005 (3)0.0038 (3)0.0006 (3)
C90.0127 (4)0.0152 (4)0.0147 (4)0.0008 (3)0.0053 (3)0.0012 (3)
C100.0135 (4)0.0163 (4)0.0193 (4)0.0009 (3)0.0050 (3)0.0006 (3)
C110.0166 (4)0.0175 (4)0.0167 (4)0.0001 (3)0.0023 (3)0.0015 (3)
C120.0133 (4)0.0147 (4)0.0145 (4)0.0015 (3)0.0033 (3)0.0005 (3)
C130.0156 (4)0.0177 (4)0.0157 (4)0.0001 (3)0.0048 (3)0.0008 (3)
C140.0237 (4)0.0172 (4)0.0160 (4)0.0003 (3)0.0041 (3)0.0003 (3)
C150.0270 (5)0.0243 (5)0.0229 (5)0.0044 (4)0.0011 (4)0.0045 (4)
C160.0345 (6)0.0300 (6)0.0210 (5)0.0003 (4)0.0133 (4)0.0043 (4)
C170.0248 (5)0.0156 (4)0.0353 (6)0.0031 (4)0.0122 (4)0.0051 (4)
C180.0340 (6)0.0195 (5)0.0530 (8)0.0043 (4)0.0281 (5)0.0040 (5)
C190.0174 (4)0.0243 (5)0.0235 (5)0.0044 (3)0.0015 (3)0.0008 (4)
Geometric parameters (Å, º) top
O1—C11.2088 (11)C9—C121.5978 (12)
O2—C21.2164 (11)C10—C121.5447 (12)
O3—C101.4323 (11)C11—C191.4823 (13)
O3—C91.4496 (10)C12—C131.5162 (12)
O4—C111.3801 (12)C13—C141.5334 (13)
O4—C101.4282 (11)C13—H13A0.9700
O5—C101.3554 (11)C13—H13B0.9700
O5—C181.4428 (12)C14—C151.5278 (14)
N1—C11.3970 (11)C14—C161.5288 (14)
N1—C21.3976 (11)C14—H14A0.9800
N1—C171.4694 (12)C15—H15A0.9600
N2—C111.2750 (12)C15—H15B0.9600
N2—C121.4623 (12)C15—H15C0.9600
C1—C91.5205 (13)C16—H16A0.9600
C2—C31.4834 (13)C16—H16B0.9600
C3—C41.3989 (12)C16—H16C0.9600
C3—C81.3990 (12)C17—H17A0.9600
C4—C51.3860 (14)C17—H17B0.9600
C4—H4A0.9300C17—H17C0.9600
C5—C61.3945 (14)C18—H18A0.9600
C5—H5A0.9300C18—H18B0.9600
C6—C71.3932 (13)C18—H18C0.9600
C6—H6A0.9300C19—H19A0.9600
C7—C81.3926 (13)C19—H19B0.9600
C7—H7A0.9300C19—H19C0.9600
C8—C91.4987 (12)
C10—O3—C992.64 (6)N2—C12—C10104.34 (7)
C11—O4—C10105.06 (7)C13—C12—C10123.48 (8)
C10—O5—C18114.85 (8)N2—C12—C9111.75 (7)
C1—N1—C2123.48 (8)C13—C12—C9116.67 (7)
C1—N1—C17118.46 (8)C10—C12—C983.08 (6)
C2—N1—C17117.55 (8)C12—C13—C14115.81 (8)
C11—N2—C12106.72 (8)C12—C13—H13A108.3
O1—C1—N1122.12 (9)C14—C13—H13A108.3
O1—C1—C9123.26 (8)C12—C13—H13B108.3
N1—C1—C9114.32 (7)C14—C13—H13B108.3
O2—C2—N1120.18 (9)H13A—C13—H13B107.4
O2—C2—C3123.13 (8)C15—C14—C16110.02 (9)
N1—C2—C3116.61 (8)C15—C14—C13112.85 (8)
C4—C3—C8120.34 (9)C16—C14—C13108.64 (8)
C4—C3—C2118.52 (8)C15—C14—H14A108.4
C8—C3—C2121.13 (8)C16—C14—H14A108.4
C5—C4—C3119.46 (9)C13—C14—H14A108.4
C5—C4—H4A120.3C14—C15—H15A109.5
C3—C4—H4A120.3C14—C15—H15B109.5
C4—C5—C6120.33 (9)H15A—C15—H15B109.5
C4—C5—H5A119.8C14—C15—H15C109.5
C6—C5—H5A119.8H15A—C15—H15C109.5
C7—C6—C5120.29 (9)H15B—C15—H15C109.5
C7—C6—H6A119.9C14—C16—H16A109.5
C5—C6—H6A119.9C14—C16—H16B109.5
C8—C7—C6119.74 (9)H16A—C16—H16B109.5
C8—C7—H7A120.1C14—C16—H16C109.5
C6—C7—H7A120.1H16A—C16—H16C109.5
C7—C8—C3119.77 (8)H16B—C16—H16C109.5
C7—C8—C9121.99 (8)N1—C17—H17A109.5
C3—C8—C9118.17 (8)N1—C17—H17B109.5
O3—C9—C8113.32 (7)H17A—C17—H17B109.5
O3—C9—C1111.77 (7)N1—C17—H17C109.5
C8—C9—C1112.62 (7)H17A—C17—H17C109.5
O3—C9—C1290.69 (6)H17B—C17—H17C109.5
C8—C9—C12116.56 (7)O5—C18—H18A109.5
C1—C9—C12110.06 (7)O5—C18—H18B109.5
O5—C10—O4111.56 (7)H18A—C18—H18B109.5
O5—C10—O3114.19 (8)O5—C18—H18C109.5
O4—C10—O3110.53 (7)H18A—C18—H18C109.5
O5—C10—C12120.31 (8)H18B—C18—H18C109.5
O4—C10—C12105.17 (7)C11—C19—H19A109.5
O3—C10—C1293.54 (6)C11—C19—H19B109.5
N2—C11—O4118.51 (8)H19A—C19—H19B109.5
N2—C11—C19126.98 (9)C11—C19—H19C109.5
O4—C11—C19114.51 (8)H19A—C19—H19C109.5
N2—C12—C13113.66 (7)H19B—C19—H19C109.5
C2—N1—C1—O1156.91 (9)C18—O5—C10—O366.90 (11)
C17—N1—C1—O114.72 (14)C18—O5—C10—C12176.84 (9)
C2—N1—C1—C929.21 (12)C11—O4—C10—O5136.31 (8)
C17—N1—C1—C9159.16 (8)C11—O4—C10—O395.49 (8)
C1—N1—C2—O2175.59 (9)C11—O4—C10—C124.29 (9)
C17—N1—C2—O23.89 (13)C9—O3—C10—O5123.77 (8)
C1—N1—C2—C31.26 (13)C9—O3—C10—O4109.48 (7)
C17—N1—C2—C3172.97 (8)C9—O3—C10—C121.83 (7)
O2—C2—C3—C410.44 (14)C12—N2—C11—O42.05 (11)
N1—C2—C3—C4166.32 (8)C12—N2—C11—C19177.58 (9)
O2—C2—C3—C8170.78 (9)C10—O4—C11—N24.29 (11)
N1—C2—C3—C812.46 (13)C10—O4—C11—C19175.38 (8)
C8—C3—C4—C51.80 (14)C11—N2—C12—C13136.26 (8)
C2—C3—C4—C5176.99 (9)C11—N2—C12—C100.94 (10)
C3—C4—C5—C62.53 (15)C11—N2—C12—C989.12 (9)
C4—C5—C6—C70.91 (15)O5—C10—C12—N2130.14 (9)
C5—C6—C7—C81.46 (14)O4—C10—C12—N23.31 (9)
C6—C7—C8—C32.17 (13)O3—C10—C12—N2109.08 (7)
C6—C7—C8—C9178.83 (8)O5—C10—C12—C131.60 (13)
C4—C3—C8—C70.55 (14)O4—C10—C12—C13128.44 (8)
C2—C3—C8—C7179.30 (8)O3—C10—C12—C13119.18 (8)
C4—C3—C8—C9177.34 (8)O5—C10—C12—C9119.11 (9)
C2—C3—C8—C93.91 (13)O4—C10—C12—C9114.06 (7)
C10—O3—C9—C8117.71 (8)O3—C10—C12—C91.67 (6)
C10—O3—C9—C1113.75 (8)O3—C9—C12—N2101.08 (7)
C10—O3—C9—C121.77 (6)C8—C9—C12—N2142.27 (8)
C7—C8—C9—O324.24 (12)C1—C9—C12—N212.45 (9)
C3—C8—C9—O3159.04 (8)O3—C9—C12—C13125.77 (8)
C7—C8—C9—C1152.34 (8)C8—C9—C12—C139.11 (11)
C3—C8—C9—C130.94 (11)C1—C9—C12—C13120.70 (8)
C7—C8—C9—C1279.06 (10)O3—C9—C12—C101.65 (6)
C3—C8—C9—C1297.65 (10)C8—C9—C12—C10115.00 (8)
O1—C1—C9—O314.35 (12)C1—C9—C12—C10115.18 (7)
N1—C1—C9—O3171.86 (7)N2—C12—C13—C1441.49 (11)
O1—C1—C9—C8143.26 (9)C10—C12—C13—C1486.40 (11)
N1—C1—C9—C842.95 (10)C9—C12—C13—C14173.78 (7)
O1—C1—C9—C1284.84 (10)C12—C13—C14—C1564.00 (11)
N1—C1—C9—C1288.95 (9)C12—C13—C14—C16173.71 (8)
C18—O5—C10—O459.32 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16B···O5i0.962.573.4213 (14)148
C17—H17C···N2ii0.962.593.5119 (14)162
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC19H22N2O5
Mr358.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)8.0488 (1), 13.6065 (2), 16.7880 (2)
β (°) 106.298 (1)
V3)1764.67 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.16 × 0.12
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.976, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
24267, 5139, 4476
Rint0.025
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.103, 1.03
No. of reflections5139
No. of parameters240
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.44, 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···AD—HH···AD···AD—H···A
C16—H16B···O5i0.962.573.4213 (14)148
C17—H17C···N2ii0.962.593.5119 (14)162
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+2, y+1, z+1.
 

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 acknowledged.

References

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Volume 67| Part 5| May 2011| Pages o1273-o1274
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