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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page o1374
https://doi.org/10.1107/S1600536810016971

(3aRS,4SR,7RS,7aSR)-2-(Tri­cyclo­[3.3.1.13,7]decan-1-yl)-4,5,6,7-tetra­hydro-4,7-ep­oxy­isoindoline-1,3-dione

Zaiyou Tan,a* Lin Luo,a Erjia Zhu,a Ruisi Yana and Zhuohui Lina

aDepartment of Physical Chemistry, Guangdong Pharmaceutical University, Guangzhou, Guangdong 510006, People's Republic of China
*Correspondence e-mail: tanzaiyou@medmail.com.cn

(Received 3 February 2010; accepted 10 May 2010; online 15 May 2010)

The title compound, C18H23NO3, the adamantane derivative of norcantharidin, which is itself derived from cantharidin, crystallized with three independent mol­ecules in the asymmetric unit. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O inter­actions, leading to the formation of a supra­molecular two-dimensional network.

Related literature

For the synthesis and anti­cancer activity of norcantharimides, see: Hill et al. (2007[Hill, T. A., Stewart, S. G., Ackland, S. P., Gilbert, J., Sauer, B., Sakoff, J. A. & McCluskey, A. (2007). Bioorg. Med. Chem. 15, 6126-6134.]); Tan (2009[Tan, Z. (2009). Chin. Patent No. CN 101172979A.]). For the synthesis and anti­cancer activity of norcantharidin, see: Shimi & Zaki (1982[Shimi, I. R. & Zaki, Z. (1982). Eur. J. Cancer Clin. Oncol. 18, 785-793.]). For background to the medicinal uses of catharidin, see: Wang (1989[Wang, G.-S. (1989). J. Ethnopharmacol. 26, 147-162.]). For the crystal structure of the phenyl derivative of norcantharidin, see: Zhu & Lin (2009[Zhu, W.-Z. & Lin, Q.-Y. (2009). Acta Cryst. E65, o287.]).

[Scheme 1]

Experimental

Crystal data

  • C18H23NO3

  • Mr = 301.37

  • Triclinic, [P \overline 1]

  • a = 12.2216 (4) Å

  • b = 12.3465 (4) Å

  • c = 16.1646 (6) Å

  • α = 77.057 (3)°

  • β = 89.906 (3)°

  • γ = 69.190 (3)°

  • V = 2213.95 (14) Å3

  • Z = 6

  • Cu Kα radiation

  • μ = 0.74 mm−1

  • T = 100 K

  • 0.2 × 0.2 × 0.1 mm
Data collection

  • Oxford Diffraction Xcalibur Onyx Nova diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.891, Tmax = 1.0

  • 15170 measured reflections

  • 7996 independent reflections

  • 7431 reflections with I > 2σ(I)

  • Rint = 0.021
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.098

  • S = 1.02

  • 7996 reflections

  • 595 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O2i 0.98 2.53 3.3332 (17) 140
C5—H5B⋯O5ii 0.97 2.59 3.4463 (18) 148
C37—H37⋯O5iii 0.98 2.38 3.3239 (16) 161
C41—H41B⋯O3iv 0.97 2.51 3.4788 (18) 176
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x, y+1, z; (iii) x-1, y, z; (iv) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810016971/su2162sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016971/su2162Isup2.hkl

checkCIF report


Comment top

Norcantharidine {(I) = 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride}, derived from cantharidin {(II) = 2,6-Dimethyl-4,10-dioxatricyclo-[5.2.1.02,6]decane-3,5-dione}, is a low toxicity anticancer drug (Shimi & Zaki, 1982). A number of norcantharimides have been synthesized from norcantharidin and have been shown to possess interesting anticancer activity (Hill et al., 2007; Tan, 2009). In order to study the relationship between the anticancer activity of norcantharidin and the adamantane norcantharimide derivative, the title compound (III) was synthesized and its crystal structure is reported on here.

Compound (III) crystallized with three independent molecules per asymmetric unit, Fig. 1. The bond distances and angles in the three independent molecules are very similar and close to those observed in a similar compound, the phenyl derivative of norcantharidin (Zhu & Lin, 2009).

In the crystal structure the individual molecules are linked via C-H···O interactions leading to the formation of a supramolecular network (Table 1).

Related literature top

For the synthesis and anticancer activity of norcantharimides, see: Hill et al. (2007); Tan (2009). For the synthesis and anticancer activity of norcantharidin, see: Shimi & Zaki (1982). For background to the medicinal uses of catharidin, see: Wang (1989). For the crystal structure of the phenyl derivative of norcantharidin, see: Zhu & Lin (2009).

Experimental top

Norcantharidin (1.0 g) and adamantine (0.9 g) were dissolved in DMF (10 mL) and the mixture was heated to reflux with stirring for 18 h. The solvent was then evaporated off and the crude product remaining was dissolved in warm acetone (10 mL) and cooled rapidly. The clear solution obtained was left undisturbed at 255 K for several days and gave finally colourless crystals of the title compound.

Refinement top

The H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.97 - 0.98 Å, with Uiso(H) = 1.2Ueq(parent C-atom).

Structure description top

Norcantharidine {(I) = 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride}, derived from cantharidin {(II) = 2,6-Dimethyl-4,10-dioxatricyclo-[5.2.1.02,6]decane-3,5-dione}, is a low toxicity anticancer drug (Shimi & Zaki, 1982). A number of norcantharimides have been synthesized from norcantharidin and have been shown to possess interesting anticancer activity (Hill et al., 2007; Tan, 2009). In order to study the relationship between the anticancer activity of norcantharidin and the adamantane norcantharimide derivative, the title compound (III) was synthesized and its crystal structure is reported on here.

Compound (III) crystallized with three independent molecules per asymmetric unit, Fig. 1. The bond distances and angles in the three independent molecules are very similar and close to those observed in a similar compound, the phenyl derivative of norcantharidin (Zhu & Lin, 2009).

In the crystal structure the individual molecules are linked via C-H···O interactions leading to the formation of a supramolecular network (Table 1).

For the synthesis and anticancer activity of norcantharimides, see: Hill et al. (2007); Tan (2009). For the synthesis and anticancer activity of norcantharidin, see: Shimi & Zaki (1982). For background to the medicinal uses of catharidin, see: Wang (1989). For the crystal structure of the phenyl derivative of norcantharidin, see: Zhu & Lin (2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the three independent molecules of compound (III). The displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Schematic views of (I), (II) and (III).
(3aRS,4SR,7RS,7aSR)-2-(Tricyclo[3.3.1.13,7]decan- 1-yl)-4,5,6,7-tetrahydro-4,7-epoxyisoindoline-1,3-dione top
Crystal data top
C18H23NO3Z = 6
Mr = 301.37F(000) = 972
Triclinic, P1Dx = 1.356 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.5418 Å
a = 12.2216 (4) ÅCell parameters from 12892 reflections
b = 12.3465 (4) Åθ = 2.8–71.2°
c = 16.1646 (6) ŵ = 0.74 mm−1
α = 77.057 (3)°T = 100 K
β = 89.906 (3)°Plate, colourless
γ = 69.190 (3)°0.2 × 0.2 × 0.1 mm
V = 2213.95 (14) Å3
Data collection top
Oxford Diffraction Xcalibur Onyx Nova
diffractometer		7996 independent reflections
Radiation source: fine-focus sealed tube7431 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.021
Detector resolution: 8.2417 pixels mm-1θmax = 68.3°, θmin = 2.8°
ω scansh = −12→14
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		k = −14→13
Tmin = 0.891, Tmax = 1.0l = −19→15
15170 measured reflections
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) = 0.098H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0465P)2 + 1.1406P]
where P = (Fo2 + 2Fc2)/3
7996 reflections(Δ/σ)max < 0.001
595 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C18H23NO3γ = 69.190 (3)°
Mr = 301.37V = 2213.95 (14) Å3
Triclinic, P1Z = 6
a = 12.2216 (4) ÅCu Kα radiation
b = 12.3465 (4) ŵ = 0.74 mm−1
c = 16.1646 (6) ÅT = 100 K
α = 77.057 (3)°0.2 × 0.2 × 0.1 mm
β = 89.906 (3)°
Data collection top
Oxford Diffraction Xcalibur Onyx Nova
diffractometer		7996 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		7431 reflections with I > 2σ(I)
Tmin = 0.891, Tmax = 1.0Rint = 0.021
15170 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.02Δρmax = 0.31 e Å−3
7996 reflectionsΔρmin = −0.22 e Å−3
595 parameters
Special details top

Experimental. CrysAlisPro (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 > σ(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
N10.80521 (9)0.52188 (9)0.17059 (6)0.0172 (2)
N21.12676 (9)0.07469 (9)0.18785 (7)0.0200 (2)
N30.19346 (10)0.00814 (10)0.51576 (7)0.0213 (2)
O10.94100 (8)0.70652 (8)0.16579 (6)0.0255 (2)
O20.82947 (8)0.54694 (10)0.02538 (6)0.0284 (2)
O30.84965 (8)0.48301 (9)0.31659 (6)0.0235 (2)
O40.91864 (9)0.10809 (9)0.05730 (6)0.0281 (2)
O51.18443 (8)−0.12995 (8)0.20189 (6)0.0263 (2)
O61.01337 (9)0.26134 (9)0.20870 (8)0.0375 (3)
O70.34150 (8)−0.22687 (9)0.44669 (6)0.0269 (2)
O80.06551 (9)0.05988 (8)0.39398 (6)0.0279 (2)
O90.31865 (11)−0.10781 (9)0.63688 (7)0.0394 (3)
C10.99762 (12)0.65254 (12)0.09882 (9)0.0236 (3)
H10.96310.69890.04130.028*
C20.98732 (11)0.52836 (11)0.12273 (8)0.0194 (3)
H21.04960.46840.10140.023*
C30.99635 (11)0.50262 (11)0.22009 (8)0.0182 (3)
H31.06110.42840.24660.022*
C41.01471 (11)0.61378 (11)0.23561 (8)0.0215 (3)
H40.99520.62840.29190.026*
C51.13899 (12)0.60702 (12)0.21473 (9)0.0240 (3)
H5A1.19670.52780.23800.029*
H5B1.16060.66490.23580.029*
C61.12610 (12)0.63743 (13)0.11592 (9)0.0257 (3)
H6A1.17920.57300.09380.031*
H6B1.13960.71040.09170.031*
C70.86623 (11)0.53358 (11)0.09782 (8)0.0194 (3)
C80.87785 (11)0.49970 (11)0.24416 (8)0.0182 (3)
C90.67839 (11)0.53414 (11)0.17438 (8)0.0173 (3)
C100.67026 (11)0.41931 (11)0.23060 (8)0.0191 (3)
H10A0.70950.35250.20560.023*
H10B0.70920.40290.28670.023*
C110.54068 (12)0.43378 (12)0.23847 (8)0.0217 (3)
H110.53600.36090.27500.026*
C120.47996 (12)0.45685 (12)0.15020 (9)0.0225 (3)
H12A0.39830.46560.15500.027*
H12B0.51780.38990.12500.027*
C130.48759 (11)0.57089 (11)0.09362 (8)0.0207 (3)
H130.44940.58530.03690.025*
C140.47916 (12)0.53976 (12)0.27779 (9)0.0234 (3)
H14A0.39770.54840.28390.028*
H14B0.51700.52550.33400.028*
C150.42546 (11)0.67717 (12)0.13211 (9)0.0233 (3)
H15A0.34340.68730.13640.028*
H15B0.42940.74950.09580.028*
C160.48527 (11)0.65468 (12)0.22058 (9)0.0225 (3)
H160.44540.72220.24580.027*
C170.61458 (11)0.64107 (11)0.21266 (8)0.0201 (3)
H17A0.61900.71330.17640.024*
H17B0.65250.62890.26840.024*
C180.61753 (11)0.55623 (11)0.08571 (8)0.0186 (3)
H18A0.65670.48950.06060.022*
H18B0.62250.62770.04880.022*
C190.92595 (12)−0.00744 (13)0.10737 (9)0.0252 (3)
H190.9715−0.07430.08330.030*
C200.97899 (11)−0.00961 (11)0.19448 (8)0.0210 (3)
H200.9604−0.06370.24170.025*
C210.92201 (11)0.12145 (11)0.19812 (8)0.0214 (3)
H210.87520.13220.24700.026*
C220.84732 (12)0.17727 (13)0.11202 (9)0.0263 (3)
H220.82820.26340.09200.032*
C230.73999 (13)0.14035 (14)0.11709 (10)0.0332 (3)
H23A0.68280.18550.06870.040*
H23B0.70270.15000.16940.040*
C240.79682 (13)0.00667 (15)0.11539 (10)0.0333 (3)
H24A0.7643−0.00970.06700.040*
H24B0.7872−0.04500.16750.040*
C251.10853 (12)−0.03268 (11)0.19481 (8)0.0205 (3)
C261.02306 (12)0.16407 (12)0.19936 (9)0.0239 (3)
C271.24486 (11)0.08634 (11)0.17863 (8)0.0191 (3)
C281.31391 (13)0.00955 (13)0.11948 (9)0.0268 (3)
H28A1.27090.03630.06380.032*
H28B1.3229−0.07300.14250.032*
C291.43579 (13)0.01918 (13)0.11085 (9)0.0284 (3)
H291.4799−0.03200.07440.034*
C301.50192 (12)−0.02155 (12)0.19902 (10)0.0276 (3)
H30A1.5115−0.10390.22390.033*
H30B1.5794−0.01710.19400.033*
C311.31319 (11)0.04571 (12)0.26620 (8)0.0215 (3)
H31A1.3234−0.03660.29150.026*
H31B1.26960.09440.30350.026*
C321.43417 (12)0.05747 (12)0.25655 (9)0.0240 (3)
H321.47790.03190.31260.029*
C331.23082 (12)0.21661 (12)0.13862 (9)0.0252 (3)
H33A1.18650.24330.08340.030*
H33B1.18760.26740.17470.030*
C341.35213 (12)0.22691 (12)0.12811 (9)0.0250 (3)
H341.34200.31020.10280.030*
C351.41880 (12)0.18701 (12)0.21611 (9)0.0247 (3)
H35A1.37560.23800.25220.030*
H35B1.49520.19410.21090.030*
C361.42049 (14)0.14850 (13)0.07055 (9)0.0291 (3)
H36A1.37810.17400.01470.035*
H36B1.49680.15550.06390.035*
C370.22597 (12)−0.21048 (12)0.41329 (8)0.0235 (3)
H370.2070−0.16800.35310.028*
C380.14640 (12)−0.14428 (12)0.47431 (8)0.0215 (3)
H380.0721−0.15780.47800.026*
C390.22433 (13)−0.19952 (12)0.55816 (8)0.0240 (3)
H390.1871−0.23650.60410.029*
C400.33389 (12)−0.29000 (12)0.53188 (9)0.0248 (3)
H400.4047−0.31330.57020.030*
C410.30524 (13)−0.39584 (12)0.51712 (9)0.0261 (3)
H41A0.3757−0.46140.51160.031*
H41B0.2630−0.42400.56260.031*
C420.22677 (13)−0.33821 (12)0.43193 (9)0.0265 (3)
H42A0.2609−0.37780.38750.032*
H42B0.1483−0.33940.43840.032*
C430.12808 (11)−0.01332 (12)0.45425 (8)0.0207 (3)
C440.25253 (13)−0.09775 (12)0.57748 (9)0.0265 (3)
C450.21348 (11)0.12225 (11)0.51530 (8)0.0203 (3)
C460.13275 (12)0.22885 (11)0.44621 (8)0.0216 (3)
H46A0.14610.21180.39050.026*
H46B0.05120.24210.45600.026*
C470.15888 (12)0.34125 (12)0.44895 (8)0.0238 (3)
H470.10720.40870.40500.029*
C480.34207 (12)0.10238 (12)0.49780 (9)0.0240 (3)
H48A0.35640.08410.44250.029*
H48B0.39400.03520.54070.029*
C490.36785 (12)0.21503 (13)0.49950 (9)0.0268 (3)
H490.45000.20180.48860.032*
C500.18965 (12)0.15242 (12)0.60276 (8)0.0232 (3)
H50A0.10800.16680.61290.028*
H50B0.23830.08570.64740.028*
C510.21730 (12)0.26423 (12)0.60447 (8)0.0232 (3)
H510.20390.28200.66060.028*
C520.13667 (12)0.36989 (12)0.53621 (9)0.0243 (3)
H52A0.05520.38430.54700.029*
H52B0.15250.44120.53740.029*
C530.34583 (13)0.24245 (12)0.58718 (9)0.0268 (3)
H53A0.39710.17590.63080.032*
H53B0.36330.31260.58910.032*
C540.28674 (13)0.32085 (13)0.43116 (9)0.0278 (3)
H54A0.30030.30450.37530.033*
H54B0.30330.39190.43180.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0230 (5)0.0189 (5)0.0326 (5)−0.0060 (4)0.0003 (4)−0.0050 (4)
O20.0247 (5)0.0459 (6)0.0176 (5)−0.0156 (4)0.0031 (4)−0.0095 (4)
O30.0252 (5)0.0321 (5)0.0165 (5)−0.0139 (4)0.0027 (4)−0.0064 (4)
O40.0275 (5)0.0336 (5)0.0204 (5)−0.0078 (4)0.0028 (4)−0.0065 (4)
O50.0238 (5)0.0176 (5)0.0350 (5)−0.0065 (4)0.0019 (4)−0.0034 (4)
O60.0328 (6)0.0246 (5)0.0626 (8)−0.0128 (4)0.0129 (5)−0.0214 (5)
O70.0256 (5)0.0265 (5)0.0292 (5)−0.0122 (4)0.0054 (4)−0.0034 (4)
O80.0305 (5)0.0235 (5)0.0278 (5)−0.0092 (4)−0.0072 (4)−0.0035 (4)
O90.0607 (8)0.0221 (5)0.0311 (6)−0.0123 (5)−0.0203 (5)−0.0019 (4)
N10.0170 (5)0.0194 (5)0.0165 (5)−0.0076 (4)0.0019 (4)−0.0054 (4)
N20.0201 (5)0.0177 (5)0.0227 (5)−0.0074 (4)−0.0001 (4)−0.0051 (4)
N30.0269 (6)0.0185 (5)0.0187 (5)−0.0090 (5)−0.0011 (4)−0.0036 (4)
C10.0230 (7)0.0252 (7)0.0220 (7)−0.0107 (5)0.0004 (5)−0.0010 (5)
C20.0184 (6)0.0215 (6)0.0188 (6)−0.0074 (5)0.0027 (5)−0.0057 (5)
C30.0185 (6)0.0182 (6)0.0183 (6)−0.0067 (5)0.0009 (5)−0.0050 (5)
C40.0233 (7)0.0213 (6)0.0218 (6)−0.0088 (5)0.0017 (5)−0.0077 (5)
C50.0236 (7)0.0250 (7)0.0271 (7)−0.0128 (6)0.0005 (5)−0.0068 (5)
C60.0242 (7)0.0296 (7)0.0261 (7)−0.0144 (6)0.0024 (5)−0.0043 (6)
C70.0216 (6)0.0194 (6)0.0178 (6)−0.0073 (5)0.0032 (5)−0.0058 (5)
C80.0211 (6)0.0162 (6)0.0183 (6)−0.0072 (5)0.0009 (5)−0.0053 (5)
C90.0166 (6)0.0182 (6)0.0184 (6)−0.0074 (5)0.0020 (5)−0.0053 (5)
C100.0198 (6)0.0186 (6)0.0194 (6)−0.0076 (5)0.0020 (5)−0.0043 (5)
C110.0229 (7)0.0210 (6)0.0231 (7)−0.0113 (5)0.0021 (5)−0.0032 (5)
C120.0207 (6)0.0235 (7)0.0271 (7)−0.0106 (5)0.0022 (5)−0.0092 (5)
C130.0188 (6)0.0224 (6)0.0212 (6)−0.0074 (5)−0.0010 (5)−0.0059 (5)
C140.0199 (6)0.0308 (7)0.0221 (6)−0.0111 (6)0.0049 (5)−0.0083 (6)
C150.0179 (6)0.0217 (7)0.0285 (7)−0.0050 (5)0.0014 (5)−0.0064 (5)
C160.0199 (6)0.0222 (7)0.0273 (7)−0.0064 (5)0.0045 (5)−0.0117 (5)
C170.0210 (6)0.0199 (6)0.0221 (6)−0.0086 (5)0.0034 (5)−0.0084 (5)
C180.0190 (6)0.0191 (6)0.0183 (6)−0.0071 (5)0.0018 (5)−0.0052 (5)
C190.0243 (7)0.0288 (7)0.0263 (7)−0.0106 (6)0.0033 (5)−0.0127 (6)
C200.0228 (7)0.0205 (6)0.0208 (6)−0.0096 (5)0.0024 (5)−0.0045 (5)
C210.0212 (6)0.0219 (7)0.0219 (6)−0.0073 (5)0.0043 (5)−0.0077 (5)
C220.0223 (7)0.0261 (7)0.0258 (7)−0.0031 (6)0.0008 (5)−0.0062 (6)
C230.0215 (7)0.0418 (9)0.0353 (8)−0.0078 (6)−0.0009 (6)−0.0134 (7)
C240.0255 (7)0.0443 (9)0.0377 (8)−0.0157 (7)0.0014 (6)−0.0201 (7)
C250.0242 (7)0.0199 (7)0.0184 (6)−0.0100 (6)0.0010 (5)−0.0032 (5)
C260.0257 (7)0.0217 (7)0.0253 (7)−0.0089 (5)0.0027 (5)−0.0070 (5)
C270.0202 (6)0.0191 (6)0.0199 (6)−0.0094 (5)0.0017 (5)−0.0053 (5)
C280.0330 (8)0.0294 (7)0.0259 (7)−0.0169 (6)0.0089 (6)−0.0132 (6)
C290.0342 (8)0.0284 (7)0.0298 (7)−0.0152 (6)0.0141 (6)−0.0151 (6)
C300.0229 (7)0.0216 (7)0.0364 (8)−0.0069 (6)0.0073 (6)−0.0053 (6)
C310.0221 (7)0.0216 (6)0.0198 (6)−0.0074 (5)0.0018 (5)−0.0038 (5)
C320.0217 (7)0.0262 (7)0.0220 (6)−0.0078 (5)−0.0013 (5)−0.0035 (5)
C330.0252 (7)0.0206 (7)0.0280 (7)−0.0093 (5)−0.0024 (6)−0.0008 (5)
C340.0291 (7)0.0194 (6)0.0271 (7)−0.0118 (6)0.0007 (6)−0.0016 (5)
C350.0240 (7)0.0266 (7)0.0281 (7)−0.0124 (6)0.0040 (5)−0.0103 (6)
C360.0352 (8)0.0346 (8)0.0227 (7)−0.0192 (7)0.0071 (6)−0.0063 (6)
C370.0276 (7)0.0249 (7)0.0189 (6)−0.0106 (6)0.0023 (5)−0.0052 (5)
C380.0242 (7)0.0223 (7)0.0212 (6)−0.0119 (5)0.0029 (5)−0.0060 (5)
C390.0346 (8)0.0201 (6)0.0185 (6)−0.0124 (6)0.0019 (5)−0.0032 (5)
C400.0277 (7)0.0214 (7)0.0243 (7)−0.0097 (6)−0.0019 (5)−0.0019 (5)
C410.0333 (7)0.0212 (7)0.0253 (7)−0.0117 (6)0.0031 (6)−0.0060 (5)
C420.0322 (7)0.0248 (7)0.0253 (7)−0.0118 (6)0.0030 (6)−0.0093 (6)
C430.0216 (6)0.0231 (7)0.0192 (6)−0.0096 (5)0.0030 (5)−0.0062 (5)
C440.0372 (8)0.0210 (7)0.0205 (7)−0.0104 (6)−0.0028 (6)−0.0035 (5)
C450.0244 (7)0.0178 (6)0.0199 (6)−0.0086 (5)0.0006 (5)−0.0054 (5)
C460.0252 (7)0.0208 (6)0.0187 (6)−0.0083 (5)−0.0003 (5)−0.0047 (5)
C470.0307 (7)0.0178 (6)0.0210 (7)−0.0078 (5)−0.0014 (5)−0.0028 (5)
C480.0237 (7)0.0229 (7)0.0261 (7)−0.0068 (5)0.0013 (5)−0.0100 (5)
C490.0228 (7)0.0285 (7)0.0344 (8)−0.0119 (6)0.0059 (6)−0.0133 (6)
C500.0294 (7)0.0219 (7)0.0187 (6)−0.0098 (6)0.0021 (5)−0.0045 (5)
C510.0310 (7)0.0215 (7)0.0175 (6)−0.0085 (6)0.0006 (5)−0.0073 (5)
C520.0279 (7)0.0194 (6)0.0247 (7)−0.0064 (5)0.0012 (5)−0.0072 (5)
C530.0300 (7)0.0222 (7)0.0294 (7)−0.0099 (6)−0.0043 (6)−0.0077 (6)
C540.0389 (8)0.0270 (7)0.0243 (7)−0.0187 (6)0.0084 (6)−0.0083 (6)
Geometric parameters (Å, º) top
O3—C81.2137 (16)C49—H490.9800
O1—C41.4450 (16)C43—C381.5091 (18)
O1—C11.4450 (17)C50—C511.5393 (18)
O2—C71.2095 (16)C50—H50A0.9700
N1—C71.3993 (16)C50—H50B0.9700
N1—C81.4009 (16)C47—C541.530 (2)
N1—C91.5053 (15)C47—C521.5304 (19)
C8—C31.5098 (17)C47—H470.9800
C18—C91.5383 (17)C38—C391.5290 (18)
C18—C131.5416 (17)C38—C371.5426 (18)
C18—H18A0.9700C38—H380.9800
C18—H18B0.9700C52—C511.5284 (18)
C9—C171.5385 (17)C52—H52B0.9700
C9—C101.5389 (17)C52—H52A0.9700
C10—C111.5378 (17)C51—H510.9800
C10—H10A0.9700C54—H54B0.9700
C10—H10B0.9700C54—H54A0.9700
C11—C121.5292 (18)C41—C401.5338 (18)
C11—C141.5342 (19)C41—H41B0.9700
C11—H110.9800C41—H41A0.9700
C7—C21.5096 (17)C39—C441.5096 (18)
C1—C61.5319 (18)C39—C401.539 (2)
C1—C21.5451 (18)C39—H390.9800
C1—H10.9800C37—H370.9800
C3—C21.5301 (17)C40—H400.9800
C3—C41.5394 (17)O4—C221.4417 (17)
C3—H30.9800O4—C191.4457 (17)
C16—C151.5290 (18)O5—C251.2096 (16)
C16—C141.5366 (19)O6—C261.2079 (17)
C16—C171.5370 (17)N2—C261.3986 (18)
C16—H160.9800N2—C251.4009 (16)
C13—C151.5302 (18)N2—C271.5044 (16)
C13—C121.5310 (18)C31—C271.5300 (17)
C13—H130.9800C31—C321.5405 (18)
C4—C51.5326 (18)C31—H31A0.9700
C4—H40.9800C31—H31B0.9700
C12—H12A0.9700C27—C281.5363 (18)
C12—H12B0.9700C27—C331.5405 (17)
C14—H14B0.9700C25—C201.5055 (18)
C14—H14A0.9700C32—C301.527 (2)
C5—C61.5514 (19)C32—C351.5294 (19)
C5—H5A0.9700C32—H320.9800
C5—H5B0.9700C20—C211.5325 (18)
C17—H17B0.9700C20—C191.5419 (18)
C17—H17A0.9700C20—H200.9800
C6—H6B0.9700C33—C341.5385 (19)
C6—H6A0.9700C33—H33A0.9700
C2—H20.9800C33—H33B0.9700
C15—H15B0.9700C35—C341.5279 (19)
C15—H15A0.9700C35—H35A0.9700
O8—C431.2115 (16)C35—H35B0.9700
O7—C371.4411 (16)C19—C241.5336 (19)
O7—C401.4431 (16)C19—H190.9800
N3—C431.4031 (16)C26—C211.5064 (18)
N3—C441.4047 (17)C22—C231.531 (2)
N3—C451.5116 (16)C22—C211.5403 (18)
O9—C441.2117 (17)C22—H220.9800
C45—C481.5380 (18)C36—C341.526 (2)
C45—C461.5413 (18)C36—C291.527 (2)
C45—C501.5426 (18)C36—H36B0.9700
C46—C471.5403 (18)C36—H36A0.9700
C46—H46A0.9700C29—C301.527 (2)
C46—H46B0.9700C29—C281.5395 (19)
C53—C491.531 (2)C29—H290.9800
C53—C511.533 (2)C34—H340.9800
C53—H53B0.9700C30—H30B0.9700
C53—H53A0.9700C30—H30A0.9700
C48—C491.5372 (18)C21—H210.9800
C48—H48B0.9700C28—H28A0.9700
C48—H48A0.9700C28—H28B0.9700
C42—C371.5343 (18)C24—C231.553 (2)
C42—C411.5501 (19)C24—H24B0.9700
C42—H42A0.9700C24—H24A0.9700
C42—H42B0.9700C23—H23A0.9700
C49—C541.532 (2)C23—H23B0.9700
C4—O1—C196.08 (9)C52—C47—H47109.1
C7—N1—C8110.70 (10)C46—C47—H47109.1
C7—N1—C9127.44 (10)C43—C38—C39105.45 (10)
C8—N1—C9121.83 (10)C43—C38—C37112.58 (11)
O3—C8—N1125.44 (12)C39—C38—C37101.30 (11)
O3—C8—C3124.66 (11)C43—C38—H38112.3
N1—C8—C3109.88 (10)C39—C38—H38112.3
C9—C18—C13109.69 (10)C37—C38—H38112.3
C9—C18—H18A109.7C51—C52—C47108.81 (11)
C13—C18—H18A109.7C51—C52—H52B109.9
C9—C18—H18B109.7C47—C52—H52B109.9
C13—C18—H18B109.7C51—C52—H52A109.9
H18A—C18—H18B108.2C47—C52—H52A109.9
N1—C9—C18112.19 (10)H52B—C52—H52A108.3
N1—C9—C17107.99 (9)C52—C51—C53109.59 (11)
C18—C9—C17108.63 (10)C52—C51—C50109.28 (11)
N1—C9—C10109.67 (10)C53—C51—C50109.86 (11)
C18—C9—C10108.23 (10)C52—C51—H51109.4
C17—C9—C10110.13 (10)C53—C51—H51109.4
C11—C10—C9109.88 (10)C50—C51—H51109.4
C11—C10—H10A109.7C47—C54—C49109.20 (11)
C9—C10—H10A109.7C47—C54—H54B109.8
C11—C10—H10B109.7C49—C54—H54B109.8
C9—C10—H10B109.7C47—C54—H54A109.8
H10A—C10—H10B108.2C49—C54—H54A109.8
C12—C11—C14109.26 (11)H54B—C54—H54A108.3
C12—C11—C10109.68 (11)C40—C41—C42101.09 (10)
C14—C11—C10109.36 (10)C40—C41—H41B111.6
C12—C11—H11109.5C42—C41—H41B111.6
C14—C11—H11109.5C40—C41—H41A111.6
C10—C11—H11109.5C42—C41—H41A111.6
O2—C7—N1126.42 (12)H41B—C41—H41A109.4
O2—C7—C2124.02 (12)C44—C39—C38104.33 (10)
N1—C7—C2109.56 (10)C44—C39—C40110.43 (12)
O1—C1—C6102.94 (11)C38—C39—C40101.94 (11)
O1—C1—C2102.52 (10)C44—C39—H39113.1
C6—C1—C2108.78 (11)C38—C39—H39113.1
O1—C1—H1113.8C40—C39—H39113.1
C6—C1—H1113.8O7—C37—C42103.06 (10)
C2—C1—H1113.8O7—C37—C38102.22 (10)
C8—C3—C2104.59 (10)C42—C37—C38108.41 (11)
C8—C3—C4111.95 (10)O7—C37—H37114.0
C2—C3—C4101.72 (10)C42—C37—H37114.0
C8—C3—H3112.6C38—C37—H37114.0
C2—C3—H3112.6O9—C44—N3125.57 (12)
C4—C3—H3112.6O9—C44—C39124.28 (12)
C15—C16—C14109.64 (11)N3—C44—C39110.14 (11)
C15—C16—C17109.31 (11)O7—C40—C41103.07 (11)
C14—C16—C17109.33 (11)O7—C40—C39101.43 (10)
C15—C16—H16109.5C41—C40—C39109.64 (11)
C14—C16—H16109.5O7—C40—H40113.8
C17—C16—H16109.5C41—C40—H40113.8
C15—C13—C12109.96 (11)C39—C40—H40113.8
C15—C13—C18109.69 (10)C22—O4—C1996.62 (10)
C12—C13—C18109.63 (10)C26—N2—C25110.24 (11)
C15—C13—H13109.2C26—N2—C27125.68 (10)
C12—C13—H13109.2C25—N2—C27123.78 (10)
C18—C13—H13109.2C27—C31—C32109.52 (10)
O1—C4—C5103.21 (10)C27—C31—H31A109.8
O1—C4—C3101.80 (10)C32—C31—H31A109.8
C5—C4—C3108.98 (11)C27—C31—H31B109.8
O1—C4—H4113.9C32—C31—H31B109.8
C5—C4—H4113.9H31A—C31—H31B108.2
C3—C4—H4113.9N2—C27—C31109.63 (10)
C11—C12—C13109.15 (10)N2—C27—C28109.72 (10)
C11—C12—H12A109.9C31—C27—C28109.83 (11)
C13—C12—H12A109.9N2—C27—C33110.72 (10)
C11—C12—H12B109.9C31—C27—C33109.24 (10)
C13—C12—H12B109.9C28—C27—C33107.68 (11)
H12A—C12—H12B108.3O5—C25—N2125.85 (12)
C11—C14—C16109.85 (11)O5—C25—C20124.58 (12)
C11—C14—H14B109.7N2—C25—C20109.56 (11)
C16—C14—H14B109.7C30—C32—C35109.08 (11)
C11—C14—H14A109.7C30—C32—C31108.84 (11)
C16—C14—H14A109.7C35—C32—C31110.06 (11)
H14B—C14—H14A108.2C30—C32—H32109.6
C4—C5—C6101.48 (10)C35—C32—H32109.6
C4—C5—H5A111.5C31—C32—H32109.6
C6—C5—H5A111.5C25—C20—C21104.67 (10)
C4—C5—H5B111.5C25—C20—C19112.13 (11)
C6—C5—H5B111.5C21—C20—C19101.61 (10)
H5A—C5—H5B109.3C25—C20—H20112.6
C16—C17—C9109.91 (10)C21—C20—H20112.6
C16—C17—H17B109.7C19—C20—H20112.6
C9—C17—H17B109.7C34—C33—C27110.20 (11)
C16—C17—H17A109.7C34—C33—H33A109.6
C9—C17—H17A109.7C27—C33—H33A109.6
H17B—C17—H17A108.2C34—C33—H33B109.6
C1—C6—C5100.99 (11)C27—C33—H33B109.6
C1—C6—H6B111.6H33A—C33—H33B108.1
C5—C6—H6B111.6C34—C35—C32109.88 (11)
C1—C6—H6A111.6C34—C35—H35A109.7
C5—C6—H6A111.6C32—C35—H35A109.7
H6B—C6—H6A109.4C34—C35—H35B109.7
C7—C2—C3105.07 (10)C32—C35—H35B109.7
C7—C2—C1112.12 (10)H35A—C35—H35B108.2
C3—C2—C1101.40 (10)O4—C19—C24103.27 (11)
C7—C2—H2112.5O4—C19—C20101.72 (10)
C3—C2—H2112.5C24—C19—C20108.22 (11)
C1—C2—H2112.5O4—C19—H19114.1
C16—C15—C13109.13 (10)C24—C19—H19114.1
C16—C15—H15B109.9C20—C19—H19114.1
C13—C15—H15B109.9O6—C26—N2126.43 (13)
C16—C15—H15A109.9O6—C26—C21123.98 (13)
C13—C15—H15A109.9N2—C26—C21109.59 (11)
H15B—C15—H15A108.3O4—C22—C23102.91 (11)
C37—O7—C4096.41 (10)O4—C22—C21102.12 (10)
C43—N3—C44110.48 (11)C23—C22—C21108.64 (12)
C43—N3—C45127.74 (10)O4—C22—H22114.0
C44—N3—C45121.44 (10)C23—C22—H22114.0
N3—C45—C48107.97 (10)C21—C22—H22114.0
N3—C45—C46112.37 (10)C34—C36—C29108.78 (11)
C48—C45—C46108.73 (11)C34—C36—H36B109.9
N3—C45—C50109.43 (10)C29—C36—H36B109.9
C48—C45—C50110.04 (10)C34—C36—H36A109.9
C46—C45—C50108.29 (11)C29—C36—H36A109.9
C47—C46—C45109.43 (10)H36B—C36—H36A108.3
C47—C46—H46A109.8C36—C29—C30110.30 (11)
C45—C46—H46A109.8C36—C29—C28109.14 (12)
C47—C46—H46B109.8C30—C29—C28109.12 (11)
C45—C46—H46B109.8C36—C29—H29109.4
H46A—C46—H46B108.2C30—C29—H29109.4
C49—C53—C51109.88 (11)C28—C29—H29109.4
C49—C53—H53B109.7C36—C34—C35110.01 (12)
C51—C53—H53B109.7C36—C34—C33110.17 (11)
C49—C53—H53A109.7C35—C34—C33108.44 (11)
C51—C53—H53A109.7C36—C34—H34109.4
H53B—C53—H53A108.2C35—C34—H34109.4
C49—C48—C45109.92 (11)C33—C34—H34109.4
C49—C48—H48B109.7C29—C30—C32110.06 (11)
C45—C48—H48B109.7C29—C30—H30B109.6
C49—C48—H48A109.7C32—C30—H30B109.6
C45—C48—H48A109.7C29—C30—H30A109.6
H48B—C48—H48A108.2C32—C30—H30A109.6
C37—C42—C41101.46 (10)H30B—C30—H30A108.2
C37—C42—H42A111.5C26—C21—C20104.72 (11)
C41—C42—H42A111.5C26—C21—C22110.82 (11)
C37—C42—H42B111.5C20—C21—C22101.73 (10)
C41—C42—H42B111.5C26—C21—H21112.9
H42A—C42—H42B109.3C20—C21—H21112.9
C53—C49—C54109.20 (12)C22—C21—H21112.9
C53—C49—C48109.20 (12)C27—C28—C29110.12 (11)
C54—C49—C48109.71 (11)C27—C28—H28A109.6
C53—C49—H49109.6C29—C28—H28A109.6
C54—C49—H49109.6C27—C28—H28B109.6
C48—C49—H49109.6C29—C28—H28B109.6
O8—C43—N3126.65 (12)H28A—C28—H28B108.2
O8—C43—C38123.90 (12)C19—C24—C23101.32 (12)
N3—C43—C38109.45 (11)C19—C24—H24B111.5
C51—C50—C45109.61 (11)C23—C24—H24B111.5
C51—C50—H50A109.7C19—C24—H24A111.5
C45—C50—H50A109.7C23—C24—H24A111.5
C51—C50—H50B109.7H24B—C24—H24A109.3
C45—C50—H50B109.7C22—C23—C24101.36 (11)
H50A—C50—H50B108.2C22—C23—H23A111.5
C54—C47—C52109.90 (11)C24—C23—H23A111.5
C54—C47—C46109.51 (11)C22—C23—H23B111.5
C52—C47—C46110.24 (11)C24—C23—H23B111.5
C54—C47—H47109.1H23A—C23—H23B109.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.982.533.3332 (17)140
C5—H5B···O5ii0.972.593.4463 (18)148
C37—H37···O5iii0.982.383.3239 (16)161
C41—H41B···O3iv0.972.513.4788 (18)176
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, y+1, z; (iii) x−1, y, z; (iv) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC18H23NO3
Mr301.37
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)12.2216 (4), 12.3465 (4), 16.1646 (6)
α, β, γ (°)77.057 (3), 89.906 (3), 69.190 (3)
V (Å3)2213.95 (14)
Z6
Radiation typeCu Kα
µ (mm−1)0.74
Crystal size (mm)0.2 × 0.2 × 0.1
Data collection
DiffractometerOxford Diffraction Xcalibur Onyx Nova
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.891, 1.0
No. of measured, independent and
observed [I > 2σ(I)] reflections		15170, 7996, 7431
Rint0.021
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.098, 1.02
No. of reflections7996
No. of parameters595
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.31, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.982.533.3332 (17)140
C5—H5B···O5ii0.972.593.4463 (18)148
C37—H37···O5iii0.982.383.3239 (16)161
C41—H41B···O3iv0.972.513.4788 (18)176
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, y+1, z; (iii) x−1, y, z; (iv) −x+1, −y, −z+1.
 

Acknowledgements

The authors acknowledge financial support from the Science and Technology Project of the Goverment of Guangdong Province, China (grant No. 2009B080701025), and Professor Xiaopeng Hu, of Sun Yat-Sen University, for his help.

References

First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationHill, T. A., Stewart, S. G., Ackland, S. P., Gilbert, J., Sauer, B., Sakoff, J. A. & McCluskey, A. (2007). Bioorg. Med. Chem. 15, 6126–6134.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShimi, I. R. & Zaki, Z. (1982). Eur. J. Cancer Clin. Oncol. 18, 785–793.  CrossRef CAS PubMed Web of Science Google Scholar
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 First citationZhu, W.-Z. & Lin, Q.-Y. (2009). Acta Cryst. E65, o287.  Web of Science CSD CrossRef IUCr Journals 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.

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ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page o1374
https://doi.org/10.1107/S1600536810016971
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