organic compounds
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
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); 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
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell 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
10.1107/S1600536811016266/lh5241sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811016266/lh5241Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811016266/lh5241Isup3.cml
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
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).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.
Data collection: APEX2 (Bruker, 2009); cell
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).Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms. |
C16H16N2O5 | F(000) = 664 |
Mr = 316.31 | Dx = 1.460 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9541 reflections |
a = 7.3643 (1) Å | θ = 2.7–38.9° |
b = 29.8703 (6) Å | µ = 0.11 mm−1 |
c = 6.7802 (1) Å | T = 100 K |
β = 105.294 (1)° | Block, colourless |
V = 1438.65 (4) Å3 | 0.46 × 0.31 × 0.27 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 8265 independent reflections |
Radiation source: fine-focus sealed tube | 6842 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ϕ and ω scans | θmax = 39.1°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→11 |
Tmin = 0.951, Tmax = 0.971 | k = −52→52 |
44501 measured reflections | l = −10→12 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-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 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C16H16N2O5 | V = 1438.65 (4) Å3 |
Mr = 316.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.3643 (1) Å | µ = 0.11 mm−1 |
b = 29.8703 (6) Å | T = 100 K |
c = 6.7802 (1) Å | 0.46 × 0.31 × 0.27 mm |
β = 105.294 (1)° |
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 = 0.971 | Rint = 0.033 |
44501 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.50 e Å−3 |
8265 reflections | Δρmin = −0.37 e Å−3 |
212 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.98692 (10) | 0.07763 (2) | 1.21672 (11) | 0.01961 (12) | |
O2 | 0.97185 (10) | 0.22835 (2) | 1.29761 (11) | 0.02036 (12) | |
O3 | 0.64272 (8) | 0.074342 (18) | 0.93351 (9) | 0.01245 (10) | |
O4 | 0.80974 (8) | 0.037356 (19) | 0.72911 (9) | 0.01405 (10) | |
O5 | 0.50850 (8) | 0.06418 (2) | 0.59672 (9) | 0.01442 (10) | |
N1 | 0.99366 (9) | 0.15373 (2) | 1.23860 (10) | 0.01288 (11) | |
N2 | 0.98329 (9) | 0.10159 (2) | 0.78175 (11) | 0.01329 (11) | |
C1 | 0.91387 (11) | 0.11323 (3) | 1.15734 (11) | 0.01266 (12) | |
C2 | 0.89437 (11) | 0.19420 (3) | 1.22005 (11) | 0.01288 (12) | |
C3 | 0.68983 (10) | 0.19200 (2) | 1.11676 (11) | 0.01123 (11) | |
C4 | 0.57505 (11) | 0.22751 (2) | 1.14283 (12) | 0.01418 (12) | |
H4A | 0.6279 | 0.2526 | 1.2171 | 0.017* | |
C5 | 0.38157 (12) | 0.22526 (3) | 1.05764 (13) | 0.01604 (13) | |
H5A | 0.3048 | 0.2489 | 1.0743 | 0.019* | |
C6 | 0.30314 (11) | 0.18742 (3) | 0.94723 (12) | 0.01532 (13) | |
H6A | 0.1739 | 0.1860 | 0.8893 | 0.018* | |
C7 | 0.41660 (11) | 0.15171 (3) | 0.92290 (11) | 0.01323 (12) | |
H7A | 0.3630 | 0.1264 | 0.8506 | 0.016* | |
C8 | 0.61080 (10) | 0.15391 (2) | 1.00719 (10) | 0.01055 (11) | |
C9 | 0.73909 (10) | 0.11699 (2) | 0.97884 (11) | 0.01041 (11) | |
C10 | 0.67607 (10) | 0.07134 (2) | 0.73762 (11) | 0.01101 (11) | |
C11 | 0.98054 (11) | 0.05895 (3) | 0.76219 (12) | 0.01374 (12) | |
C12 | 0.79021 (10) | 0.11558 (2) | 0.76495 (11) | 0.01075 (11) | |
C13 | 0.72971 (12) | 0.15463 (3) | 0.62183 (12) | 0.01482 (13) | |
H13A | 0.7495 | 0.1475 | 0.4909 | 0.022* | |
H13B | 0.8025 | 0.1806 | 0.6771 | 0.022* | |
H13C | 0.5986 | 0.1607 | 0.6063 | 0.022* | |
C14 | 1.18102 (12) | 0.15176 (3) | 1.38319 (13) | 0.01961 (15) | |
H14A | 1.2585 | 0.1311 | 1.3338 | 0.029* | |
H14B | 1.1695 | 0.1420 | 1.5143 | 0.029* | |
H14C | 1.2376 | 0.1809 | 1.3961 | 0.029* | |
C15 | 0.51787 (13) | 0.05535 (3) | 0.39061 (13) | 0.02037 (15) | |
H15A | 0.3927 | 0.0530 | 0.3024 | 0.031* | |
H15B | 0.5840 | 0.0278 | 0.3874 | 0.031* | |
H15C | 0.5831 | 0.0794 | 0.3447 | 0.031* | |
C16 | 1.14282 (12) | 0.02931 (3) | 0.76728 (17) | 0.02177 (17) | |
H16A | 1.2575 | 0.0462 | 0.8101 | 0.033* | |
H16B | 1.1314 | 0.0173 | 0.6333 | 0.033* | |
H16C | 1.1448 | 0.0053 | 0.8618 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0194 (3) | 0.0141 (2) | 0.0220 (3) | 0.0030 (2) | −0.0004 (2) | 0.0036 (2) |
O2 | 0.0186 (3) | 0.0147 (3) | 0.0249 (3) | −0.0053 (2) | 0.0006 (2) | −0.0044 (2) |
O3 | 0.0150 (2) | 0.0102 (2) | 0.0132 (2) | −0.00369 (17) | 0.00555 (17) | −0.00184 (17) |
O4 | 0.0112 (2) | 0.0101 (2) | 0.0215 (3) | −0.00064 (17) | 0.00536 (18) | −0.00282 (18) |
O5 | 0.0113 (2) | 0.0169 (2) | 0.0144 (2) | −0.00187 (18) | 0.00209 (17) | −0.00453 (19) |
N1 | 0.0106 (2) | 0.0138 (3) | 0.0126 (2) | −0.00073 (19) | 0.00022 (18) | −0.0006 (2) |
N2 | 0.0113 (2) | 0.0118 (2) | 0.0179 (3) | −0.00080 (19) | 0.0059 (2) | −0.0016 (2) |
C1 | 0.0126 (3) | 0.0126 (3) | 0.0121 (3) | 0.0000 (2) | 0.0022 (2) | 0.0005 (2) |
C2 | 0.0132 (3) | 0.0125 (3) | 0.0123 (3) | −0.0019 (2) | 0.0022 (2) | −0.0002 (2) |
C3 | 0.0124 (3) | 0.0104 (3) | 0.0106 (2) | −0.0008 (2) | 0.0026 (2) | 0.0001 (2) |
C4 | 0.0174 (3) | 0.0106 (3) | 0.0146 (3) | 0.0006 (2) | 0.0044 (2) | −0.0004 (2) |
C5 | 0.0169 (3) | 0.0143 (3) | 0.0176 (3) | 0.0039 (2) | 0.0058 (2) | 0.0005 (2) |
C6 | 0.0117 (3) | 0.0175 (3) | 0.0164 (3) | 0.0022 (2) | 0.0031 (2) | 0.0001 (2) |
C7 | 0.0113 (3) | 0.0146 (3) | 0.0133 (3) | 0.0000 (2) | 0.0022 (2) | −0.0016 (2) |
C8 | 0.0114 (3) | 0.0107 (3) | 0.0095 (2) | −0.0003 (2) | 0.00277 (19) | −0.0006 (2) |
C9 | 0.0110 (3) | 0.0094 (2) | 0.0107 (2) | −0.0013 (2) | 0.00248 (19) | −0.0008 (2) |
C10 | 0.0104 (3) | 0.0102 (3) | 0.0127 (3) | −0.0006 (2) | 0.0035 (2) | −0.0015 (2) |
C11 | 0.0116 (3) | 0.0123 (3) | 0.0183 (3) | −0.0008 (2) | 0.0056 (2) | −0.0020 (2) |
C12 | 0.0112 (3) | 0.0098 (3) | 0.0117 (3) | −0.0006 (2) | 0.0040 (2) | −0.0009 (2) |
C13 | 0.0187 (3) | 0.0124 (3) | 0.0145 (3) | 0.0010 (2) | 0.0064 (2) | 0.0021 (2) |
C14 | 0.0131 (3) | 0.0241 (4) | 0.0178 (3) | −0.0014 (3) | −0.0026 (2) | 0.0012 (3) |
C15 | 0.0215 (4) | 0.0237 (4) | 0.0149 (3) | −0.0007 (3) | 0.0030 (3) | −0.0056 (3) |
C16 | 0.0140 (3) | 0.0152 (3) | 0.0374 (5) | 0.0019 (3) | 0.0092 (3) | −0.0041 (3) |
O1—C1 | 1.2116 (10) | C6—C7 | 1.3914 (11) |
O2—C2 | 1.2183 (9) | C6—H6A | 0.9300 |
O3—C10 | 1.4158 (9) | C7—C8 | 1.3946 (10) |
O3—C9 | 1.4512 (9) | C7—H7A | 0.9300 |
O4—C11 | 1.3784 (9) | C8—C9 | 1.4972 (10) |
O4—C10 | 1.4257 (9) | C9—C12 | 1.5921 (10) |
O5—C10 | 1.3636 (9) | C10—C12 | 1.5508 (10) |
O5—C15 | 1.4416 (10) | C11—C16 | 1.4804 (11) |
N1—C1 | 1.3933 (10) | C12—C13 | 1.5075 (10) |
N1—C2 | 1.4012 (10) | C13—H13A | 0.9600 |
N1—C14 | 1.4679 (10) | C13—H13B | 0.9600 |
N2—C11 | 1.2799 (10) | C13—H13C | 0.9600 |
N2—C12 | 1.4574 (10) | C14—H14A | 0.9600 |
C1—C9 | 1.5206 (10) | C14—H14B | 0.9600 |
C2—C3 | 1.4857 (10) | C14—H14C | 0.9600 |
C3—C4 | 1.3961 (10) | C15—H15A | 0.9600 |
C3—C8 | 1.3990 (10) | C15—H15B | 0.9600 |
C4—C5 | 1.3907 (12) | C15—H15C | 0.9600 |
C4—H4A | 0.9300 | C16—H16A | 0.9600 |
C5—C6 | 1.3941 (12) | C16—H16B | 0.9600 |
C5—H5A | 0.9300 | C16—H16C | 0.9600 |
C10—O3—C9 | 93.33 (5) | O5—C10—O4 | 111.53 (6) |
C11—O4—C10 | 105.68 (6) | O3—C10—O4 | 112.06 (6) |
C10—O5—C15 | 116.23 (6) | O5—C10—C12 | 125.39 (6) |
C1—N1—C2 | 123.91 (6) | O3—C10—C12 | 93.25 (5) |
C1—N1—C14 | 116.97 (7) | O4—C10—C12 | 104.67 (6) |
C2—N1—C14 | 118.08 (7) | N2—C11—O4 | 118.12 (7) |
C11—N2—C12 | 106.79 (6) | N2—C11—C16 | 127.02 (7) |
O1—C1—N1 | 121.77 (7) | O4—C11—C16 | 114.85 (7) |
O1—C1—C9 | 122.53 (7) | N2—C12—C13 | 112.88 (6) |
N1—C1—C9 | 115.52 (6) | N2—C12—C10 | 104.58 (6) |
O2—C2—N1 | 120.65 (7) | C13—C12—C10 | 121.57 (6) |
O2—C2—C3 | 122.79 (7) | N2—C12—C9 | 113.37 (6) |
N1—C2—C3 | 116.38 (6) | C13—C12—C9 | 117.72 (6) |
C4—C3—C8 | 120.27 (7) | C10—C12—C9 | 83.13 (5) |
C4—C3—C2 | 118.63 (7) | C12—C13—H13A | 109.5 |
C8—C3—C2 | 120.95 (6) | C12—C13—H13B | 109.5 |
C5—C4—C3 | 119.93 (7) | H13A—C13—H13B | 109.5 |
C5—C4—H4A | 120.0 | C12—C13—H13C | 109.5 |
C3—C4—H4A | 120.0 | H13A—C13—H13C | 109.5 |
C4—C5—C6 | 119.74 (7) | H13B—C13—H13C | 109.5 |
C4—C5—H5A | 120.1 | N1—C14—H14A | 109.5 |
C6—C5—H5A | 120.1 | N1—C14—H14B | 109.5 |
C7—C6—C5 | 120.57 (7) | H14A—C14—H14B | 109.5 |
C7—C6—H6A | 119.7 | N1—C14—H14C | 109.5 |
C5—C6—H6A | 119.7 | H14A—C14—H14C | 109.5 |
C6—C7—C8 | 119.88 (7) | H14B—C14—H14C | 109.5 |
C6—C7—H7A | 120.1 | O5—C15—H15A | 109.5 |
C8—C7—H7A | 120.1 | O5—C15—H15B | 109.5 |
C7—C8—C3 | 119.60 (7) | H15A—C15—H15B | 109.5 |
C7—C8—C9 | 121.75 (6) | O5—C15—H15C | 109.5 |
C3—C8—C9 | 118.62 (6) | H15A—C15—H15C | 109.5 |
O3—C9—C8 | 112.58 (6) | H15B—C15—H15C | 109.5 |
O3—C9—C1 | 111.58 (6) | C11—C16—H16A | 109.5 |
C8—C9—C1 | 112.49 (6) | C11—C16—H16B | 109.5 |
O3—C9—C12 | 90.22 (5) | H16A—C16—H16B | 109.5 |
C8—C9—C12 | 116.44 (6) | C11—C16—H16C | 109.5 |
C1—C9—C12 | 111.66 (6) | H16A—C16—H16C | 109.5 |
O5—C10—O3 | 108.56 (6) | H16B—C16—H16C | 109.5 |
C2—N1—C1—O1 | −161.40 (8) | O1—C1—C9—C12 | −81.94 (9) |
C14—N1—C1—O1 | 6.68 (11) | N1—C1—C9—C12 | 93.26 (7) |
C2—N1—C1—C9 | 23.35 (10) | C15—O5—C10—O3 | −173.45 (6) |
C14—N1—C1—C9 | −168.56 (7) | C15—O5—C10—O4 | −49.51 (9) |
C1—N1—C2—O2 | 178.82 (8) | C15—O5—C10—C12 | 78.38 (9) |
C14—N1—C2—O2 | 10.86 (11) | C9—O3—C10—O5 | −126.97 (6) |
C1—N1—C2—C3 | 3.52 (10) | C9—O3—C10—O4 | 109.41 (6) |
C14—N1—C2—C3 | −164.44 (7) | C9—O3—C10—C12 | 2.15 (6) |
O2—C2—C3—C4 | −12.66 (11) | C11—O4—C10—O5 | 142.09 (6) |
N1—C2—C3—C4 | 162.54 (7) | C11—O4—C10—O3 | −95.97 (7) |
O2—C2—C3—C8 | 171.75 (7) | C11—O4—C10—C12 | 3.77 (7) |
N1—C2—C3—C8 | −13.05 (10) | C12—N2—C11—O4 | 0.91 (9) |
C8—C3—C4—C5 | −0.74 (11) | C12—N2—C11—C16 | 179.69 (8) |
C2—C3—C4—C5 | −176.36 (7) | C10—O4—C11—N2 | −3.21 (9) |
C3—C4—C5—C6 | 0.27 (12) | C10—O4—C11—C16 | 177.86 (7) |
C4—C5—C6—C7 | 0.53 (12) | C11—N2—C12—C13 | −132.59 (7) |
C5—C6—C7—C8 | −0.85 (12) | C11—N2—C12—C10 | 1.60 (8) |
C6—C7—C8—C3 | 0.38 (11) | C11—N2—C12—C9 | 90.33 (7) |
C6—C7—C8—C9 | −177.87 (7) | O5—C10—C12—N2 | −133.99 (7) |
C4—C3—C8—C7 | 0.41 (10) | O3—C10—C12—N2 | 110.46 (6) |
C2—C3—C8—C7 | 175.93 (7) | O4—C10—C12—N2 | −3.35 (7) |
C4—C3—C8—C9 | 178.71 (7) | O5—C10—C12—C13 | −4.83 (10) |
C2—C3—C8—C9 | −5.77 (10) | O3—C10—C12—C13 | −120.39 (7) |
C10—O3—C9—C8 | 116.84 (6) | O4—C10—C12—C13 | 125.81 (7) |
C10—O3—C9—C1 | −115.57 (6) | O5—C10—C12—C9 | 113.59 (7) |
C10—O3—C9—C12 | −2.09 (5) | O3—C10—C12—C9 | −1.97 (5) |
C7—C8—C9—O3 | −23.21 (9) | O4—C10—C12—C9 | −115.78 (6) |
C3—C8—C9—O3 | 158.52 (6) | O3—C9—C12—N2 | −101.04 (6) |
C7—C8—C9—C1 | −150.32 (7) | C8—C9—C12—N2 | 143.45 (6) |
C3—C8—C9—C1 | 31.42 (9) | C1—C9—C12—N2 | 12.37 (8) |
C7—C8—C9—C12 | 78.99 (8) | O3—C9—C12—C13 | 124.09 (7) |
C3—C8—C9—C12 | −99.28 (7) | C8—C9—C12—C13 | 8.58 (9) |
O1—C1—C9—O3 | 17.35 (10) | C1—C9—C12—C13 | −122.51 (7) |
N1—C1—C9—O3 | −167.44 (6) | O3—C9—C12—C10 | 1.92 (5) |
O1—C1—C9—C8 | 144.99 (8) | C8—C9—C12—C10 | −113.59 (6) |
N1—C1—C9—C8 | −39.81 (9) | C1—C9—C12—C10 | 115.32 (6) |
Experimental details
Crystal data | |
Chemical formula | C16H16N2O5 |
Mr | 316.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 7.3643 (1), 29.8703 (6), 6.7802 (1) |
β (°) | 105.294 (1) |
V (Å3) | 1438.65 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.46 × 0.31 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.951, 0.971 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 44501, 8265, 6842 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.887 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.126, 1.08 |
No. of reflections | 8265 |
No. of parameters | 212 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.37 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 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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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.