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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 May 7;67(Pt 6):o1340–o1341. doi: 10.1107/S1600536811016266

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

Hoong-Kun Fun a,*,‡, Ching Kheng Quah a,§, Chengmei Huang b, Haitao Yu b
PMCID: PMC3120469  PMID: 21754736

Abstract

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 ▶).graphic file with name e-67-o1340-scheme1.jpg

Experimental

Crystal data

  • C16H16N2O5

  • M r = 316.31

  • Monoclinic, Inline graphic

  • 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 ▶) T min = 0.951, T max = 0.971

  • 44501 measured reflections

  • 8265 independent reflections

  • 6842 reflections with I > 2σ(I)

  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049

  • wR(F 2) = 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 ▶); 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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016266/lh5241sup1.cif

e-67-o1340-sup1.cif (20.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016266/lh5241Isup2.hkl

e-67-o1340-Isup2.hkl (404.3KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811016266/lh5241Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.

Crystal data

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
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Data collection

Bruker SMART APEXII CCD area-detector diffractometer 8265 independent reflections
Radiation source: fine-focus sealed tube 6842 reflections with I > 2σ(I)
graphite 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
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Refinement

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
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5241).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016266/lh5241sup1.cif

e-67-o1340-sup1.cif (20.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016266/lh5241Isup2.hkl

e-67-o1340-Isup2.hkl (404.3KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811016266/lh5241Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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