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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 6| June 2011| Pages o1340-o1341

5-Meth­­oxy-1,2′,3-tri­methyl-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 21 April 2011; accepted 29 April 2011; online 7 May 2011)

In the isoquinoline ring system of the title mol­ecule, C16H16N2O5, the N-heterocyclic ring is in a half-boat conformation. The dioxaaza­spiro ring is essentially planar [maximum deviation = 0.022 (1) Å] and forms a dihedral angle of 24.56 (4)° with the benzene ring.

Related literature

For general background to and the potential biological activity of the title compound, see: 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.]); 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.]); 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.]); Zhang et al. (2004[Zhang, Y., Wang, L., Zhang, M., Fun, H.-K. & Xu, J.-X. (2004). Org. Lett. 6, 4893-4895.]); 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 related structures, see: Fun et al. (2011a[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011a). Acta Cryst. E67, o1271-o1272.],b[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011b). Acta Cryst. E67, o1272-o1273.],c[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011c). Acta Cryst. E67, o1311-o1312.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O5

  • Mr = 316.31

  • Monoclinic, P 21 /c

  • a = 7.3643 (1) Å

  • b = 29.8703 (6) Å

  • c = 6.7802 (1) Å

  • β = 105.294 (1)°

  • V = 1438.65 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.46 × 0.31 × 0.27 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 = 0.951, Tmax = 0.971

  • 44501 measured reflections

  • 8265 independent reflections

  • 6842 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.126

  • S = 1.08

  • 8265 reflections

  • 212 parameters

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.37 e Å−3

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

Isoquinoline-1,3,4-trione derivatives have been 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). Photoreactions of isoquinoline-1,3,4-trione could lead to structurally important motifs (Yu et al., 2010). Oxazole ring is 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 isoquinoline or oxazole ring are bioactive, convenient method to construct such moieties is of current research interest (Zhang et al., 2004; Wang et al., 2010). 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. 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 0.231 (1) Å from the mean plane through the remaining atoms, puckering parameters (Cremer & Pople, 1975) Q = 0.3501 (8) Å, Θ = 112.83 (13)° and ϕ = 282.17 (13)°. The dioxa-2-azaspiro ring (N2/O4/C10-C12) is essentially planar [maximum deviation of 0.022 (1) Å at atom C10] and it inclines at a dihedral angle of 24.56 (4)° with the benzene ring (C3-C8). Bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to related structures (Fun et al., 2011a,b,c). In the crystal of the title compound, unlike in our previously determined structures mentioned above, there are no significant intermolecular hydrogen bonds.

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 related structures, see: Fun et al. (2011a,b,c).

Experimental top

The title compound was the main product from the photoreaction between isoquinoline-1,3,4-trione and 4-methyl-5-methoxy-2-methyloxazole. The compound was purified by flash column chromatography with ethyl acetate/petroleum ether (1:3) as eluents. X-ray quality crystals of the title compound was obtained from slow evaporation of an acetone and petroleum ether solution (1:4) (m.p. 437-439 K).

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C–H = 0.93 - 0.96 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl groups. The highest residual electron density peak is located at 0.77 Å from C9 and the deepest hole is located at 0.52 Å from C2.

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.
5-Methoxy-1,2',3-trimethyl-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
C16H16N2O5F(000) = 664
Mr = 316.31Dx = 1.460 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9541 reflections
a = 7.3643 (1) Åθ = 2.7–38.9°
b = 29.8703 (6) ŵ = 0.11 mm1
c = 6.7802 (1) ÅT = 100 K
β = 105.294 (1)°Block, colourless
V = 1438.65 (4) Å30.46 × 0.31 × 0.27 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
8265 independent reflections
Radiation source: fine-focus sealed tube6842 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 39.1°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1311
Tmin = 0.951, Tmax = 0.971k = 5252
44501 measured reflectionsl = 1012
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0561P)2 + 0.4048P]
where P = (Fo2 + 2Fc2)/3
8265 reflections(Δ/σ)max = 0.001
212 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C16H16N2O5V = 1438.65 (4) Å3
Mr = 316.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.3643 (1) ŵ = 0.11 mm1
b = 29.8703 (6) ÅT = 100 K
c = 6.7802 (1) Å0.46 × 0.31 × 0.27 mm
β = 105.294 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
8265 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6842 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.971Rint = 0.033
44501 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.08Δρmax = 0.50 e Å3
8265 reflectionsΔρmin = 0.37 e Å3
212 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
O10.98692 (10)0.07763 (2)1.21672 (11)0.01961 (12)
O20.97185 (10)0.22835 (2)1.29761 (11)0.02036 (12)
O30.64272 (8)0.074342 (18)0.93351 (9)0.01245 (10)
O40.80974 (8)0.037356 (19)0.72911 (9)0.01405 (10)
O50.50850 (8)0.06418 (2)0.59672 (9)0.01442 (10)
N10.99366 (9)0.15373 (2)1.23860 (10)0.01288 (11)
N20.98329 (9)0.10159 (2)0.78175 (11)0.01329 (11)
C10.91387 (11)0.11323 (3)1.15734 (11)0.01266 (12)
C20.89437 (11)0.19420 (3)1.22005 (11)0.01288 (12)
C30.68983 (10)0.19200 (2)1.11676 (11)0.01123 (11)
C40.57505 (11)0.22751 (2)1.14283 (12)0.01418 (12)
H4A0.62790.25261.21710.017*
C50.38157 (12)0.22526 (3)1.05764 (13)0.01604 (13)
H5A0.30480.24891.07430.019*
C60.30314 (11)0.18742 (3)0.94723 (12)0.01532 (13)
H6A0.17390.18600.88930.018*
C70.41660 (11)0.15171 (3)0.92290 (11)0.01323 (12)
H7A0.36300.12640.85060.016*
C80.61080 (10)0.15391 (2)1.00719 (10)0.01055 (11)
C90.73909 (10)0.11699 (2)0.97884 (11)0.01041 (11)
C100.67607 (10)0.07134 (2)0.73762 (11)0.01101 (11)
C110.98054 (11)0.05895 (3)0.76219 (12)0.01374 (12)
C120.79021 (10)0.11558 (2)0.76495 (11)0.01075 (11)
C130.72971 (12)0.15463 (3)0.62183 (12)0.01482 (13)
H13A0.74950.14750.49090.022*
H13B0.80250.18060.67710.022*
H13C0.59860.16070.60630.022*
C141.18102 (12)0.15176 (3)1.38319 (13)0.01961 (15)
H14A1.25850.13111.33380.029*
H14B1.16950.14201.51430.029*
H14C1.23760.18091.39610.029*
C150.51787 (13)0.05535 (3)0.39061 (13)0.02037 (15)
H15A0.39270.05300.30240.031*
H15B0.58400.02780.38740.031*
H15C0.58310.07940.34470.031*
C161.14282 (12)0.02931 (3)0.76728 (17)0.02177 (17)
H16A1.25750.04620.81010.033*
H16B1.13140.01730.63330.033*
H16C1.14480.00530.86180.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0194 (3)0.0141 (2)0.0220 (3)0.0030 (2)0.0004 (2)0.0036 (2)
O20.0186 (3)0.0147 (3)0.0249 (3)0.0053 (2)0.0006 (2)0.0044 (2)
O30.0150 (2)0.0102 (2)0.0132 (2)0.00369 (17)0.00555 (17)0.00184 (17)
O40.0112 (2)0.0101 (2)0.0215 (3)0.00064 (17)0.00536 (18)0.00282 (18)
O50.0113 (2)0.0169 (2)0.0144 (2)0.00187 (18)0.00209 (17)0.00453 (19)
N10.0106 (2)0.0138 (3)0.0126 (2)0.00073 (19)0.00022 (18)0.0006 (2)
N20.0113 (2)0.0118 (2)0.0179 (3)0.00080 (19)0.0059 (2)0.0016 (2)
C10.0126 (3)0.0126 (3)0.0121 (3)0.0000 (2)0.0022 (2)0.0005 (2)
C20.0132 (3)0.0125 (3)0.0123 (3)0.0019 (2)0.0022 (2)0.0002 (2)
C30.0124 (3)0.0104 (3)0.0106 (2)0.0008 (2)0.0026 (2)0.0001 (2)
C40.0174 (3)0.0106 (3)0.0146 (3)0.0006 (2)0.0044 (2)0.0004 (2)
C50.0169 (3)0.0143 (3)0.0176 (3)0.0039 (2)0.0058 (2)0.0005 (2)
C60.0117 (3)0.0175 (3)0.0164 (3)0.0022 (2)0.0031 (2)0.0001 (2)
C70.0113 (3)0.0146 (3)0.0133 (3)0.0000 (2)0.0022 (2)0.0016 (2)
C80.0114 (3)0.0107 (3)0.0095 (2)0.0003 (2)0.00277 (19)0.0006 (2)
C90.0110 (3)0.0094 (2)0.0107 (2)0.0013 (2)0.00248 (19)0.0008 (2)
C100.0104 (3)0.0102 (3)0.0127 (3)0.0006 (2)0.0035 (2)0.0015 (2)
C110.0116 (3)0.0123 (3)0.0183 (3)0.0008 (2)0.0056 (2)0.0020 (2)
C120.0112 (3)0.0098 (3)0.0117 (3)0.0006 (2)0.0040 (2)0.0009 (2)
C130.0187 (3)0.0124 (3)0.0145 (3)0.0010 (2)0.0064 (2)0.0021 (2)
C140.0131 (3)0.0241 (4)0.0178 (3)0.0014 (3)0.0026 (2)0.0012 (3)
C150.0215 (4)0.0237 (4)0.0149 (3)0.0007 (3)0.0030 (3)0.0056 (3)
C160.0140 (3)0.0152 (3)0.0374 (5)0.0019 (3)0.0092 (3)0.0041 (3)
Geometric parameters (Å, º) top
O1—C11.2116 (10)C6—C71.3914 (11)
O2—C21.2183 (9)C6—H6A0.9300
O3—C101.4158 (9)C7—C81.3946 (10)
O3—C91.4512 (9)C7—H7A0.9300
O4—C111.3784 (9)C8—C91.4972 (10)
O4—C101.4257 (9)C9—C121.5921 (10)
O5—C101.3636 (9)C10—C121.5508 (10)
O5—C151.4416 (10)C11—C161.4804 (11)
N1—C11.3933 (10)C12—C131.5075 (10)
N1—C21.4012 (10)C13—H13A0.9600
N1—C141.4679 (10)C13—H13B0.9600
N2—C111.2799 (10)C13—H13C0.9600
N2—C121.4574 (10)C14—H14A0.9600
C1—C91.5206 (10)C14—H14B0.9600
C2—C31.4857 (10)C14—H14C0.9600
C3—C41.3961 (10)C15—H15A0.9600
C3—C81.3990 (10)C15—H15B0.9600
C4—C51.3907 (12)C15—H15C0.9600
C4—H4A0.9300C16—H16A0.9600
C5—C61.3941 (12)C16—H16B0.9600
C5—H5A0.9300C16—H16C0.9600
C10—O3—C993.33 (5)O5—C10—O4111.53 (6)
C11—O4—C10105.68 (6)O3—C10—O4112.06 (6)
C10—O5—C15116.23 (6)O5—C10—C12125.39 (6)
C1—N1—C2123.91 (6)O3—C10—C1293.25 (5)
C1—N1—C14116.97 (7)O4—C10—C12104.67 (6)
C2—N1—C14118.08 (7)N2—C11—O4118.12 (7)
C11—N2—C12106.79 (6)N2—C11—C16127.02 (7)
O1—C1—N1121.77 (7)O4—C11—C16114.85 (7)
O1—C1—C9122.53 (7)N2—C12—C13112.88 (6)
N1—C1—C9115.52 (6)N2—C12—C10104.58 (6)
O2—C2—N1120.65 (7)C13—C12—C10121.57 (6)
O2—C2—C3122.79 (7)N2—C12—C9113.37 (6)
N1—C2—C3116.38 (6)C13—C12—C9117.72 (6)
C4—C3—C8120.27 (7)C10—C12—C983.13 (5)
C4—C3—C2118.63 (7)C12—C13—H13A109.5
C8—C3—C2120.95 (6)C12—C13—H13B109.5
C5—C4—C3119.93 (7)H13A—C13—H13B109.5
C5—C4—H4A120.0C12—C13—H13C109.5
C3—C4—H4A120.0H13A—C13—H13C109.5
C4—C5—C6119.74 (7)H13B—C13—H13C109.5
C4—C5—H5A120.1N1—C14—H14A109.5
C6—C5—H5A120.1N1—C14—H14B109.5
C7—C6—C5120.57 (7)H14A—C14—H14B109.5
C7—C6—H6A119.7N1—C14—H14C109.5
C5—C6—H6A119.7H14A—C14—H14C109.5
C6—C7—C8119.88 (7)H14B—C14—H14C109.5
C6—C7—H7A120.1O5—C15—H15A109.5
C8—C7—H7A120.1O5—C15—H15B109.5
C7—C8—C3119.60 (7)H15A—C15—H15B109.5
C7—C8—C9121.75 (6)O5—C15—H15C109.5
C3—C8—C9118.62 (6)H15A—C15—H15C109.5
O3—C9—C8112.58 (6)H15B—C15—H15C109.5
O3—C9—C1111.58 (6)C11—C16—H16A109.5
C8—C9—C1112.49 (6)C11—C16—H16B109.5
O3—C9—C1290.22 (5)H16A—C16—H16B109.5
C8—C9—C12116.44 (6)C11—C16—H16C109.5
C1—C9—C12111.66 (6)H16A—C16—H16C109.5
O5—C10—O3108.56 (6)H16B—C16—H16C109.5
C2—N1—C1—O1161.40 (8)O1—C1—C9—C1281.94 (9)
C14—N1—C1—O16.68 (11)N1—C1—C9—C1293.26 (7)
C2—N1—C1—C923.35 (10)C15—O5—C10—O3173.45 (6)
C14—N1—C1—C9168.56 (7)C15—O5—C10—O449.51 (9)
C1—N1—C2—O2178.82 (8)C15—O5—C10—C1278.38 (9)
C14—N1—C2—O210.86 (11)C9—O3—C10—O5126.97 (6)
C1—N1—C2—C33.52 (10)C9—O3—C10—O4109.41 (6)
C14—N1—C2—C3164.44 (7)C9—O3—C10—C122.15 (6)
O2—C2—C3—C412.66 (11)C11—O4—C10—O5142.09 (6)
N1—C2—C3—C4162.54 (7)C11—O4—C10—O395.97 (7)
O2—C2—C3—C8171.75 (7)C11—O4—C10—C123.77 (7)
N1—C2—C3—C813.05 (10)C12—N2—C11—O40.91 (9)
C8—C3—C4—C50.74 (11)C12—N2—C11—C16179.69 (8)
C2—C3—C4—C5176.36 (7)C10—O4—C11—N23.21 (9)
C3—C4—C5—C60.27 (12)C10—O4—C11—C16177.86 (7)
C4—C5—C6—C70.53 (12)C11—N2—C12—C13132.59 (7)
C5—C6—C7—C80.85 (12)C11—N2—C12—C101.60 (8)
C6—C7—C8—C30.38 (11)C11—N2—C12—C990.33 (7)
C6—C7—C8—C9177.87 (7)O5—C10—C12—N2133.99 (7)
C4—C3—C8—C70.41 (10)O3—C10—C12—N2110.46 (6)
C2—C3—C8—C7175.93 (7)O4—C10—C12—N23.35 (7)
C4—C3—C8—C9178.71 (7)O5—C10—C12—C134.83 (10)
C2—C3—C8—C95.77 (10)O3—C10—C12—C13120.39 (7)
C10—O3—C9—C8116.84 (6)O4—C10—C12—C13125.81 (7)
C10—O3—C9—C1115.57 (6)O5—C10—C12—C9113.59 (7)
C10—O3—C9—C122.09 (5)O3—C10—C12—C91.97 (5)
C7—C8—C9—O323.21 (9)O4—C10—C12—C9115.78 (6)
C3—C8—C9—O3158.52 (6)O3—C9—C12—N2101.04 (6)
C7—C8—C9—C1150.32 (7)C8—C9—C12—N2143.45 (6)
C3—C8—C9—C131.42 (9)C1—C9—C12—N212.37 (8)
C7—C8—C9—C1278.99 (8)O3—C9—C12—C13124.09 (7)
C3—C8—C9—C1299.28 (7)C8—C9—C12—C138.58 (9)
O1—C1—C9—O317.35 (10)C1—C9—C12—C13122.51 (7)
N1—C1—C9—O3167.44 (6)O3—C9—C12—C101.92 (5)
O1—C1—C9—C8144.99 (8)C8—C9—C12—C10113.59 (6)
N1—C1—C9—C839.81 (9)C1—C9—C12—C10115.32 (6)

Experimental details

Crystal data
Chemical formulaC16H16N2O5
Mr316.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)7.3643 (1), 29.8703 (6), 6.7802 (1)
β (°) 105.294 (1)
V3)1438.65 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.46 × 0.31 × 0.27
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.951, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
44501, 8265, 6842
Rint0.033
(sin θ/λ)max1)0.887
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.126, 1.08
No. of reflections8265
No. of parameters212
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.37

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

 

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.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, 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.  Web of Science CrossRef PubMed CAS Google Scholar
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationDu, 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.  CrossRef CAS Google Scholar
First citationFun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011a). Acta Cryst. E67, o1271–o1272.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationFun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011b). Acta Cryst. E67, o1272–o1273.  Google Scholar
First citationFun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011c). Acta Cryst. E67, o1311–o1312.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHarris, 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.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHuang, C., Yu, H., Miao, Z., Zhou, J., Wang, S., Fun, H.-K., Xu, J. & Zhang, Y. (2011). Org. Biomol. Chem. 9 3629–3631.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, L., Huang, Y. C., Liu, Y., Fun, H.-K., Zhang, Y. & Xu, J. H. (2010). J. Org. Chem. 75, 7757–7768.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationYu, H., Li, J., Kou, Z., Du, X., Wei, Y., Fun, H.-K., Xu, J. & Zhang, Y. (2010). J. Org. Chem. 75, 2989–3001.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationZhang, Y., Wang, L., Zhang, M., Fun, H.-K. & Xu, J.-X. (2004). Org. Lett. 6, 4893–4895.  Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 6| June 2011| Pages o1340-o1341
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds