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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 8| August 2013| Pages o1199-o1200

14-Meth­­oxy-4,6-di­methyl-9-phenyl-8,12-dioxa-4,6-di­aza­tetra­cyclo­[8.8.0.02,7.013,18]octa­deca-2(7),13,15,17-tetra­ene-3,5,11-trione

aDepartment of Physics, Presidency College, Chennai 600 005, India, bCenter for Advanced Study in Botany, University of Madras, Guindy Campus, Chennai 600 025, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: aravindhanpresidency@gmail.com

(Received 12 June 2013; accepted 28 June 2013; online 3 July 2013)

The title compound, C23H20N2O6, crystallizes with two mol­ecules in the asymmetric unit in which the dihedral angles between the mean planes of the pyran and phenyl rings are 66.6 (1) and 61.9 (1) °. The fused pyrone and pyran rings each adopts a sofa conformation. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules, forming a two-dimensional network parallel to [001].

Related literature

For the biological activity of pyran­ocoumarin compounds, see: Kawaii et al. (2001[Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., Ito, C. & Furukawa, H. (2001). Anticancer Res. 21, 1905-1911.]); Hossain et al. (1996[Hossain, C. F., Okuyama, E. & Yamazaki, M. (1996). Chem. Pharm. Bull. (Tokyo), 44, 1535-1539.]); Goel et al. (1997[Goel, R. K., Maiti, R. N., Manickam, M. & Ray, A. B. (1997). Indian J. Exp. Biol. 35, 1080-1083.]); Su et al. (2009[Su, C. R., Yeh, S. F., Liu, C. M., Damu, A. G., Kuo, T. H., Chiang, P. C., Bastow, K. F., Lee, K. H. & Wu, T. S. (2009). Bioorg. Med. Chem. 17, 6137-6143.]); Xu et al. (2006[Xu, Z. Q., Pupek, K., Suling, W. J., Enache, L. & Flavin, M. T. (2006). Bioorg. Med. Chem. 14, 4610-4626.]). For anti-filarial activity studies of pyran­ocoumarin compounds, see: Casley-Smith et al. (1993[Casley-Smith, J. R., Wang, C. T., Casley-Smith, J. R. & Zi-hai, C. (1993). Br. Med. J. 307, 1037-1041.]) and for enzyme inhibitory activity of pyran­ocoumarin compounds, see: Pavao et al. (2002[Pavao, F., Castilho, M. S., Pupo, M. T., Dias, R. L. A., Correa, A. G., Fernandes, J. B., Da Silva, M. F. G. F., Mafezoli, J., Vieir, P. C. & Oliva, G. (2002). FEBS Lett. 520, 13-17.]). For a related structure, see: Jagadeesan et al. (2013[Jagadeesan, G., Kannan, D., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o80.]).

[Scheme 1]

Experimental

Crystal data
  • C23H20N2O6

  • Mr = 420.41

  • Triclinic, [P \overline 1]

  • a = 9.2283 (7) Å

  • b = 14.0584 (10) Å

  • c = 16.4457 (13) Å

  • α = 94.869 (2)°

  • β = 102.547 (2)°

  • γ = 105.270 (2)°

  • V = 1986.1 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.983

  • 36657 measured reflections

  • 7558 independent reflections

  • 5648 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.141

  • S = 1.06

  • 7558 reflections

  • 588 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C21A—H21A⋯O5Bi 0.93 2.55 3.435 (4) 159
C20B—H20B⋯O5Aii 0.93 2.34 3.175 (3) 149
C23B—H23D⋯O6Biii 0.96 2.46 3.249 (4) 139
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+2, -z+1; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Coumarin derivatives show strong activity against cancer cell lines (Kawaii et al., 2001) and exhibit monoamine oxidase inhibitory activity (Hossain et al., 1996). Antiulcer activity of some naturally occurring pyranocoumarins has been reported (Goel et al., 1997). They also show anti-hepatitis B virus, anti-filarial (Casley-Smith et al., 1993) and cytotoxic activities (Su et al., 2009) and anti-TB activity (Xu et al., 2006). One natural source coumarin derivative, Chalepin, inhibits the glyceraldehyde-3-phosphate dehydrogenase of parasites (Protein Data Bank ID code 1 K3T) (Pavao et al., 2002). Herein, we report on the crystal structure of the title coumarin derivative.

We have already reported a similar compound (Jagadeesan et al., 2013). The title compound crystallizes with two molecules in the asymmetric unit. Geometrical parameters are almost similar the title compound and the previously reported structure. The six-membered pyrone and pyran rings adopt a sofa conformation. The dihedral angle between the mean planes of the pyran and phenyl rings is 66.6 (1) ° and 61.9 (1) ° for the molecule A and B respectively. The crystal packing is stabilized by C—H···O intermolecular hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For the biological activity of pyranocoumarin compounds, see: Kawaii et al. (2001); Hossain et al. (1996); Goel et al. (1997); Su et al. (2009); Xu et al. (2006). For anti-filarial activity studies of pyranocoumarin compounds, see: Casley-Smith et al. (1993) and for enzyme inhibitory activity of pyranocoumarin compounds, see: Pavao et al. (2002). For a related structure, see: Jagadeesan et al. (2013).

Experimental top

A mixture of 2-ethoxy-6-formylphenyl (2E)-but-2-enoate (0.234 g, 1 mmol) and N,N-dimethylbarbituric acid (0.156 g, 1 mmol) was placed in a round bottom flask and melted at 180 °C for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethylacetate and hexane mixture (1:49 ratio) which successfully provided the pure product in 90% yield as colorless solid. Diffraction quality crystals were obtained by slow evaporation of a solution in (Methonal and ethanol)6:4 ratio.

Refinement top

H atoms (except H7A, H7B, H8A, H8B, H9A and H9B atom which were freely refined) were refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] using a riding model with C—H ranging from 0.93 Å to 0.97 Å. The methyl groups bonded to N were refined as disordered over two equally occupied sites rotated by 60 degrees.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level, H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in the interactions have been omitted.
14-Methoxy-4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-diazatetracyclo[8.8.0.02,7.013,18]octadeca-2(7),13,15,17-tetraene-3,5,11-trione top
Crystal data top
C23H20N2O6Z = 4
Mr = 420.41F(000) = 880
Triclinic, P1Dx = 1.406 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2283 (7) ÅCell parameters from 8834 reflections
b = 14.0584 (10) Åθ = 2.1–31.2°
c = 16.4457 (13) ŵ = 0.10 mm1
α = 94.869 (2)°T = 293 K
β = 102.547 (2)°Block, colourless
γ = 105.270 (2)°0.25 × 0.20 × 0.20 mm
V = 1986.1 (3) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7558 independent reflections
Radiation source: fine-focus sealed tube5648 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω and ϕ scanθmax = 25.7°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker 2004)
h = 1111
Tmin = 0.979, Tmax = 0.983k = 1717
36657 measured reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.0528P)2 + 1.2155P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
7558 reflectionsΔρmax = 0.22 e Å3
588 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0041 (7)
Crystal data top
C23H20N2O6γ = 105.270 (2)°
Mr = 420.41V = 1986.1 (3) Å3
Triclinic, P1Z = 4
a = 9.2283 (7) ÅMo Kα radiation
b = 14.0584 (10) ŵ = 0.10 mm1
c = 16.4457 (13) ÅT = 293 K
α = 94.869 (2)°0.25 × 0.20 × 0.20 mm
β = 102.547 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7558 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker 2004)
5648 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.983Rint = 0.029
36657 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.22 e Å3
7558 reflectionsΔρmin = 0.18 e Å3
588 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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*/UeqOcc. (<1)
O1A0.43958 (18)0.84184 (11)0.13771 (9)0.0433 (4)
O3A0.62793 (19)0.60615 (11)0.25301 (10)0.0491 (4)
N1A0.4243 (2)0.98731 (13)0.19611 (11)0.0408 (4)
O6A0.3970 (2)1.13287 (12)0.25056 (11)0.0653 (5)
O5A0.6491 (2)0.96419 (12)0.42706 (10)0.0587 (5)
O1B1.0081 (2)1.35732 (12)0.17540 (11)0.0542 (4)
O2B0.7090 (2)1.04069 (13)0.08928 (10)0.0558 (4)
O3B0.8419 (2)1.03414 (11)0.21441 (10)0.0500 (4)
O2A0.7740 (2)0.66004 (13)0.16873 (11)0.0553 (4)
C11A0.4727 (2)0.90470 (15)0.20928 (13)0.0354 (5)
N2A0.5173 (2)1.04671 (13)0.34024 (11)0.0447 (5)
C9A0.6168 (3)0.80548 (15)0.29473 (13)0.0370 (5)
C10A0.5470 (3)0.89086 (15)0.28534 (13)0.0371 (5)
C24A0.6857 (3)0.67602 (16)0.20697 (14)0.0417 (5)
C17A0.5294 (3)0.71943 (15)0.33133 (13)0.0381 (5)
O4A0.4761 (2)0.45275 (12)0.30578 (12)0.0642 (5)
N1B1.0045 (2)1.49711 (14)0.25095 (14)0.0557 (5)
O5B0.7679 (2)1.34929 (14)0.40134 (12)0.0643 (5)
C14A0.4427 (3)1.06042 (15)0.26200 (14)0.0439 (5)
C6A0.4536 (3)0.69790 (17)0.05832 (14)0.0436 (5)
C11B0.9629 (3)1.39480 (16)0.23985 (15)0.0453 (6)
N2B0.8912 (3)1.49558 (14)0.36477 (13)0.0540 (5)
C8B0.8289 (3)1.19799 (16)0.17843 (14)0.0407 (5)
C18A0.5376 (3)0.62478 (16)0.30704 (14)0.0400 (5)
C10B0.8851 (3)1.34072 (16)0.28866 (14)0.0424 (5)
C18B0.9296 (3)1.08267 (16)0.29447 (14)0.0424 (5)
O4B1.0043 (2)0.93660 (13)0.30200 (13)0.0700 (6)
C22A0.4416 (3)0.72982 (17)0.38821 (14)0.0470 (6)
H22A0.43210.79230.40490.056*
C13B0.8415 (3)1.39109 (17)0.35471 (16)0.0489 (6)
C8A0.6299 (3)0.76749 (16)0.20753 (14)0.0382 (5)
C24B0.7878 (3)1.08628 (16)0.15531 (14)0.0411 (5)
C9B0.8319 (3)1.22862 (15)0.26978 (14)0.0397 (5)
C7B0.9863 (3)1.25026 (17)0.16340 (15)0.0450 (5)
C19A0.4606 (3)0.54112 (16)0.33674 (15)0.0469 (6)
C17B0.9294 (3)1.17652 (16)0.32621 (14)0.0421 (5)
O6B1.0114 (2)1.64095 (13)0.32677 (14)0.0782 (6)
C13A0.5775 (3)0.96662 (16)0.35610 (14)0.0423 (5)
C7A0.4712 (3)0.74697 (16)0.14575 (14)0.0394 (5)
C14B0.9705 (3)1.55068 (17)0.31511 (18)0.0560 (7)
C6B1.0041 (3)1.22284 (18)0.07678 (15)0.0470 (6)
C21A0.3684 (3)0.64850 (19)0.42018 (16)0.0552 (6)
H21A0.31240.65700.45950.066*
C15A0.3540 (3)1.00239 (18)0.11075 (14)0.0508 (6)
H15A0.29651.04970.11430.076*0.50
H15B0.28560.94010.07950.076*0.50
H15C0.43421.02720.08270.076*0.50
H15D0.38100.96160.07000.076*0.50
H15E0.39191.07130.10490.076*0.50
H15F0.24330.98410.10170.076*0.50
C2B1.0921 (3)1.1218 (2)0.01454 (18)0.0654 (7)
H2B1.14181.07330.02200.079*
C16A0.5385 (4)1.12317 (18)0.41195 (16)0.0638 (8)
H16A0.54811.09420.46290.096*0.50
H16B0.45051.14880.40370.096*0.50
H16C0.63071.17650.41600.096*0.50
H16D0.53811.18550.39220.096*0.50
H16E0.63571.13090.45140.096*0.50
H16F0.45551.10310.43910.096*0.50
C1A0.3713 (3)0.59853 (19)0.03436 (17)0.0594 (7)
H1A0.32770.56270.07250.071*
C5B0.9430 (4)1.2624 (2)0.00862 (18)0.0640 (7)
H5B0.89121.30980.01570.077*
C20A0.3767 (3)0.55408 (18)0.39469 (16)0.0547 (6)
H20A0.32610.49960.41650.066*
C20B1.1029 (4)1.0712 (2)0.42048 (17)0.0660 (8)
H20B1.16021.03640.45310.079*
C19B1.0153 (3)1.02850 (18)0.34063 (16)0.0510 (6)
C16B0.8547 (4)1.5509 (2)0.43332 (19)0.0728 (9)
H16G0.82321.50670.47180.109*0.50
H16H0.77211.57810.41050.109*0.50
H16I0.94501.60410.46260.109*0.50
H16J0.87031.61920.42480.109*0.50
H16K0.92141.54780.48610.109*0.50
H16L0.74861.52180.43400.109*0.50
C22B1.0194 (4)1.2177 (2)0.40600 (16)0.0621 (7)
H22B1.02191.28120.42880.075*
C23A0.3997 (4)0.36508 (19)0.3349 (2)0.0740 (9)
H23A0.42030.30820.30840.111*
H23B0.29000.35630.32090.111*
H23C0.43740.37170.39490.111*
C4A0.4996 (4)0.7023 (3)0.07899 (17)0.0719 (8)
H4A0.54370.73740.11730.086*
C3A0.4174 (4)0.6034 (3)0.10228 (19)0.0758 (10)
H3A0.40550.57150.15630.091*
C2A0.3535 (4)0.5522 (2)0.0460 (2)0.0766 (9)
H2A0.29730.48530.06190.092*
C5A0.5171 (3)0.7500 (2)0.00085 (16)0.0579 (7)
H5A0.57170.81730.01600.069*
C1B1.0790 (3)1.1524 (2)0.06444 (17)0.0595 (7)
H1B1.12141.12510.11010.071*
C3B1.0330 (3)1.1619 (2)0.08186 (19)0.0670 (8)
H3B1.04341.14170.13510.080*
C23B1.0990 (4)0.8826 (2)0.3457 (2)0.0904 (11)
H23D1.08070.81920.31230.136*
H23E1.07390.87230.39860.136*
H23F1.20620.91980.35570.136*
C15B1.0871 (4)1.5530 (2)0.1958 (2)0.0786 (9)
H15G1.12151.62270.21820.118*0.50
H15H1.01901.54280.14060.118*0.50
H15I1.17521.53010.19220.118*0.50
H15J1.08891.50770.14910.118*0.50
H15K1.19151.58760.22680.118*0.50
H15L1.03531.60030.17520.118*0.50
C21B1.1056 (4)1.1655 (2)0.45203 (18)0.0757 (9)
H21B1.16701.19460.50560.091*
C4B0.9580 (4)1.2323 (2)0.07059 (19)0.0745 (9)
H4B0.91691.25990.11640.089*
H8A0.703 (3)0.8181 (16)0.1882 (13)0.040 (6)*
H9A0.723 (3)0.8307 (15)0.3302 (13)0.036 (6)*
H7A0.393 (3)0.7075 (17)0.1685 (14)0.041 (6)*
H7B1.071 (3)1.2327 (17)0.2088 (15)0.050 (6)*
H9B0.724 (3)1.2058 (16)0.2746 (14)0.043 (6)*
H8B0.750 (3)1.2190 (17)0.1387 (15)0.048 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0583 (10)0.0410 (8)0.0318 (8)0.0254 (7)0.0018 (7)0.0004 (6)
O3A0.0613 (10)0.0405 (8)0.0584 (10)0.0253 (7)0.0263 (9)0.0144 (7)
N1A0.0528 (11)0.0378 (9)0.0348 (10)0.0206 (8)0.0080 (8)0.0063 (7)
O6A0.1003 (15)0.0422 (9)0.0583 (11)0.0361 (10)0.0117 (10)0.0054 (8)
O5A0.0825 (13)0.0518 (10)0.0337 (9)0.0201 (9)0.0012 (9)0.0015 (7)
O1B0.0591 (11)0.0416 (9)0.0684 (12)0.0125 (8)0.0287 (9)0.0163 (8)
O2B0.0619 (11)0.0555 (10)0.0412 (10)0.0129 (8)0.0046 (8)0.0052 (8)
O3B0.0636 (11)0.0352 (8)0.0442 (9)0.0123 (7)0.0018 (8)0.0038 (7)
O2A0.0584 (11)0.0557 (10)0.0633 (11)0.0266 (8)0.0267 (9)0.0097 (8)
C11A0.0394 (12)0.0331 (10)0.0338 (11)0.0117 (9)0.0084 (9)0.0037 (8)
N2A0.0644 (13)0.0330 (9)0.0360 (10)0.0129 (8)0.0140 (9)0.0017 (7)
C9A0.0395 (12)0.0371 (11)0.0322 (11)0.0126 (9)0.0029 (10)0.0042 (9)
C10A0.0457 (12)0.0328 (10)0.0334 (11)0.0119 (9)0.0099 (9)0.0057 (8)
C24A0.0420 (13)0.0429 (12)0.0419 (13)0.0159 (10)0.0097 (11)0.0057 (10)
C17A0.0434 (12)0.0392 (11)0.0307 (11)0.0135 (9)0.0041 (9)0.0073 (9)
O4A0.0877 (14)0.0372 (9)0.0766 (13)0.0218 (9)0.0317 (11)0.0158 (8)
N1B0.0546 (13)0.0355 (10)0.0732 (15)0.0094 (9)0.0105 (11)0.0137 (10)
O5B0.0829 (14)0.0570 (11)0.0583 (11)0.0210 (10)0.0300 (10)0.0032 (9)
C14A0.0569 (14)0.0314 (11)0.0438 (13)0.0122 (10)0.0143 (11)0.0051 (9)
C6A0.0476 (13)0.0443 (12)0.0392 (12)0.0220 (10)0.0029 (10)0.0004 (10)
C11B0.0420 (13)0.0385 (12)0.0542 (15)0.0133 (10)0.0068 (11)0.0076 (10)
N2B0.0594 (13)0.0400 (11)0.0569 (13)0.0198 (9)0.0004 (10)0.0034 (9)
C8B0.0435 (13)0.0410 (12)0.0391 (12)0.0142 (10)0.0096 (10)0.0096 (9)
C18A0.0443 (13)0.0411 (12)0.0382 (12)0.0178 (10)0.0098 (10)0.0093 (9)
C10B0.0440 (13)0.0357 (11)0.0459 (13)0.0124 (9)0.0069 (10)0.0058 (9)
C18B0.0495 (13)0.0365 (11)0.0389 (12)0.0098 (9)0.0088 (10)0.0072 (9)
O4B0.0868 (14)0.0456 (10)0.0782 (13)0.0314 (9)0.0049 (11)0.0136 (9)
C22A0.0609 (15)0.0447 (13)0.0382 (13)0.0185 (11)0.0145 (11)0.0062 (10)
C13B0.0514 (14)0.0429 (13)0.0497 (14)0.0180 (11)0.0035 (12)0.0009 (11)
C8A0.0405 (12)0.0379 (11)0.0390 (12)0.0141 (9)0.0111 (10)0.0084 (9)
C24B0.0439 (13)0.0417 (12)0.0384 (13)0.0116 (10)0.0130 (10)0.0057 (10)
C9B0.0442 (13)0.0353 (11)0.0386 (12)0.0100 (9)0.0100 (10)0.0060 (9)
C7B0.0470 (14)0.0441 (12)0.0483 (14)0.0171 (10)0.0141 (11)0.0124 (10)
C19A0.0538 (14)0.0383 (12)0.0488 (14)0.0147 (10)0.0099 (11)0.0108 (10)
C17B0.0497 (13)0.0393 (12)0.0372 (12)0.0117 (10)0.0110 (10)0.0084 (9)
O6B0.0784 (14)0.0347 (10)0.1059 (17)0.0141 (9)0.0036 (12)0.0029 (10)
C13A0.0521 (14)0.0356 (11)0.0369 (12)0.0085 (9)0.0108 (10)0.0068 (9)
C7A0.0459 (13)0.0361 (11)0.0363 (12)0.0151 (10)0.0074 (10)0.0036 (9)
C14B0.0517 (15)0.0361 (13)0.0696 (18)0.0162 (11)0.0089 (13)0.0015 (12)
C6B0.0453 (13)0.0522 (13)0.0522 (14)0.0183 (11)0.0202 (11)0.0200 (11)
C21A0.0680 (17)0.0575 (15)0.0455 (14)0.0183 (13)0.0237 (13)0.0110 (11)
C15A0.0648 (16)0.0473 (13)0.0412 (13)0.0262 (12)0.0018 (11)0.0093 (10)
C2B0.0679 (19)0.080 (2)0.0646 (18)0.0361 (15)0.0311 (15)0.0143 (15)
C16A0.105 (2)0.0425 (14)0.0419 (14)0.0209 (14)0.0193 (14)0.0039 (11)
C1A0.0709 (18)0.0472 (14)0.0573 (16)0.0205 (12)0.0111 (14)0.0049 (12)
C5B0.0758 (19)0.0689 (18)0.0648 (18)0.0357 (15)0.0288 (15)0.0288 (14)
C20A0.0630 (16)0.0463 (14)0.0544 (15)0.0099 (11)0.0176 (13)0.0168 (11)
C20B0.077 (2)0.0672 (18)0.0556 (17)0.0316 (15)0.0022 (14)0.0217 (14)
C19B0.0570 (15)0.0427 (13)0.0544 (15)0.0164 (11)0.0106 (12)0.0150 (11)
C16B0.089 (2)0.0595 (17)0.0654 (18)0.0384 (16)0.0015 (16)0.0133 (14)
C22B0.087 (2)0.0553 (15)0.0397 (14)0.0265 (14)0.0031 (13)0.0002 (11)
C23A0.084 (2)0.0372 (14)0.098 (2)0.0115 (13)0.0205 (18)0.0200 (14)
C4A0.094 (2)0.090 (2)0.0437 (16)0.0452 (19)0.0195 (15)0.0082 (15)
C3A0.098 (2)0.090 (2)0.0429 (16)0.055 (2)0.0001 (16)0.0169 (16)
C2A0.090 (2)0.0618 (18)0.068 (2)0.0281 (16)0.0031 (18)0.0222 (16)
C5A0.0720 (18)0.0593 (15)0.0439 (15)0.0230 (13)0.0154 (13)0.0014 (12)
C1B0.0658 (17)0.0744 (18)0.0565 (16)0.0391 (14)0.0254 (14)0.0213 (13)
C3B0.0686 (19)0.082 (2)0.0587 (18)0.0176 (15)0.0343 (15)0.0174 (15)
C23B0.096 (3)0.0618 (19)0.123 (3)0.0421 (18)0.015 (2)0.0345 (19)
C15B0.085 (2)0.0473 (16)0.101 (2)0.0049 (14)0.0274 (19)0.0289 (16)
C21B0.098 (2)0.076 (2)0.0435 (15)0.0330 (17)0.0105 (15)0.0042 (14)
C4B0.091 (2)0.084 (2)0.0600 (19)0.0308 (18)0.0271 (17)0.0381 (16)
Geometric parameters (Å, º) top
O1A—C11A1.336 (2)O6B—C14B1.210 (3)
O1A—C7A1.449 (2)C7A—H7A0.95 (2)
O3A—C24A1.359 (3)C6B—C5B1.371 (3)
O3A—C18A1.397 (3)C6B—C1B1.374 (3)
N1A—C11A1.367 (3)C21A—C20A1.385 (4)
N1A—C14A1.378 (3)C21A—H21A0.9300
N1A—C15A1.471 (3)C15A—H15A0.9600
O6A—C14A1.214 (3)C15A—H15B0.9600
O5A—C13A1.218 (3)C15A—H15C0.9600
O1B—C11B1.337 (3)C15A—H15D0.9600
O1B—C7B1.455 (3)C15A—H15E0.9600
O2B—C24B1.188 (3)C15A—H15F0.9600
O3B—C24B1.354 (3)C2B—C3B1.359 (4)
O3B—C18B1.396 (3)C2B—C1B1.374 (4)
O2A—C24A1.186 (3)C2B—H2B0.9300
C11A—C10A1.346 (3)C16A—H16A0.9600
N2A—C14A1.376 (3)C16A—H16B0.9600
N2A—C13A1.401 (3)C16A—H16C0.9600
N2A—C16A1.469 (3)C16A—H16D0.9600
C9A—C10A1.508 (3)C16A—H16E0.9600
C9A—C17A1.515 (3)C16A—H16F0.9600
C9A—C8A1.529 (3)C1A—C2A1.379 (4)
C9A—H9A0.98 (2)C1A—H1A0.9300
C10A—C13A1.434 (3)C5B—C4B1.382 (4)
C24A—C8A1.506 (3)C5B—H5B0.9300
C17A—C18A1.383 (3)C20A—H20A0.9300
C17A—C22A1.386 (3)C20B—C21B1.374 (4)
O4A—C19A1.357 (3)C20B—C19B1.374 (4)
O4A—C23A1.426 (3)C20B—H20B0.9300
N1B—C11B1.372 (3)C16B—H16G0.9600
N1B—C14B1.383 (3)C16B—H16H0.9600
N1B—C15B1.459 (4)C16B—H16I0.9600
O5B—C13B1.219 (3)C16B—H16J0.9600
C6A—C1A1.379 (3)C16B—H16K0.9600
C6A—C5A1.380 (4)C16B—H16L0.9600
C6A—C7A1.497 (3)C22B—C21B1.372 (4)
C11B—C10B1.343 (3)C22B—H22B0.9300
N2B—C14B1.368 (4)C23A—H23A0.9600
N2B—C13B1.402 (3)C23A—H23B0.9600
N2B—C16B1.463 (3)C23A—H23C0.9600
C8B—C24B1.509 (3)C4A—C3A1.373 (5)
C8B—C9B1.519 (3)C4A—C5A1.379 (4)
C8B—C7B1.528 (3)C4A—H4A0.9300
C8B—H8B0.99 (2)C3A—C2A1.359 (5)
C18A—C19A1.391 (3)C3A—H3A0.9300
C10B—C13B1.432 (3)C2A—H2A0.9300
C10B—C9B1.505 (3)C5A—H5A0.9300
C18B—C17B1.378 (3)C1B—H1B0.9300
C18B—C19B1.392 (3)C3B—C4B1.371 (4)
O4B—C19B1.359 (3)C3B—H3B0.9300
O4B—C23B1.424 (3)C23B—H23D0.9600
C22A—C21A1.374 (3)C23B—H23E0.9600
C22A—H22A0.9300C23B—H23F0.9600
C8A—C7A1.531 (3)C15B—H15G0.9600
C8A—H8A0.97 (2)C15B—H15H0.9600
C9B—C17B1.519 (3)C15B—H15I0.9600
C9B—H9B0.99 (2)C15B—H15J0.9600
C7B—C6B1.499 (3)C15B—H15K0.9600
C7B—H7B1.06 (2)C15B—H15L0.9600
C19A—C20A1.380 (4)C21B—H21B0.9300
C17B—C22B1.375 (3)C4B—H4B0.9300
C11A—O1A—C7A116.19 (16)N1A—C15A—H15F109.5
C24A—O3A—C18A121.01 (17)H15A—C15A—H15F56.3
C11A—N1A—C14A121.25 (18)H15B—C15A—H15F56.3
C11A—N1A—C15A121.10 (18)H15C—C15A—H15F141.1
C14A—N1A—C15A117.64 (18)H15D—C15A—H15F109.5
C11B—O1B—C7B116.98 (17)H15E—C15A—H15F109.5
C24B—O3B—C18B120.60 (17)C3B—C2B—C1B120.5 (3)
O1A—C11A—C10A125.08 (19)C3B—C2B—H2B119.8
O1A—C11A—N1A111.66 (17)C1B—C2B—H2B119.8
C10A—C11A—N1A123.25 (19)N2A—C16A—H16A109.5
C14A—N2A—C13A124.81 (18)N2A—C16A—H16B109.5
C14A—N2A—C16A117.42 (19)H16A—C16A—H16B109.5
C13A—N2A—C16A117.8 (2)N2A—C16A—H16C109.5
C10A—C9A—C17A115.84 (19)H16A—C16A—H16C109.5
C10A—C9A—C8A107.27 (16)H16B—C16A—H16C109.5
C17A—C9A—C8A109.59 (17)N2A—C16A—H16D109.5
C10A—C9A—H9A109.1 (12)H16A—C16A—H16D141.1
C17A—C9A—H9A108.2 (12)H16B—C16A—H16D56.3
C8A—C9A—H9A106.4 (13)H16C—C16A—H16D56.3
C11A—C10A—C13A118.46 (19)N2A—C16A—H16E109.5
C11A—C10A—C9A121.14 (19)H16A—C16A—H16E56.3
C13A—C10A—C9A119.85 (19)H16B—C16A—H16E141.1
O2A—C24A—O3A117.9 (2)H16C—C16A—H16E56.3
O2A—C24A—C8A125.0 (2)H16D—C16A—H16E109.5
O3A—C24A—C8A117.06 (19)N2A—C16A—H16F109.5
C18A—C17A—C22A117.7 (2)H16A—C16A—H16F56.3
C18A—C17A—C9A118.41 (19)H16B—C16A—H16F56.3
C22A—C17A—C9A123.88 (19)H16C—C16A—H16F141.1
C19A—O4A—C23A117.9 (2)H16D—C16A—H16F109.5
C11B—N1B—C14B121.2 (2)H16E—C16A—H16F109.5
C11B—N1B—C15B121.0 (2)C6A—C1A—C2A120.1 (3)
C14B—N1B—C15B117.8 (2)C6A—C1A—H1A120.0
O6A—C14A—N2A122.7 (2)C2A—C1A—H1A120.0
O6A—C14A—N1A121.3 (2)C6B—C5B—C4B120.4 (3)
N2A—C14A—N1A116.01 (19)C6B—C5B—H5B119.8
C1A—C6A—C5A119.2 (2)C4B—C5B—H5B119.8
C1A—C6A—C7A119.3 (2)C19A—C20A—C21A119.7 (2)
C5A—C6A—C7A121.5 (2)C19A—C20A—H20A120.1
O1B—C11B—C10B125.2 (2)C21A—C20A—H20A120.1
O1B—C11B—N1B112.0 (2)C21B—C20B—C19B119.8 (2)
C10B—C11B—N1B122.8 (2)C21B—C20B—H20B120.1
C14B—N2B—C13B125.3 (2)C19B—C20B—H20B120.1
C14B—N2B—C16B116.9 (2)O4B—C19B—C20B125.5 (2)
C13B—N2B—C16B117.9 (2)O4B—C19B—C18B116.3 (2)
C24B—C8B—C9B112.13 (18)C20B—C19B—C18B118.2 (2)
C24B—C8B—C7B111.53 (19)N2B—C16B—H16G109.5
C9B—C8B—C7B108.64 (19)N2B—C16B—H16H109.5
C24B—C8B—H8B105.6 (14)H16G—C16B—H16H109.5
C9B—C8B—H8B112.2 (14)N2B—C16B—H16I109.5
C7B—C8B—H8B106.6 (14)H16G—C16B—H16I109.5
C17A—C18A—C19A122.6 (2)H16H—C16B—H16I109.5
C17A—C18A—O3A122.64 (19)N2B—C16B—H16J109.5
C19A—C18A—O3A114.73 (19)H16G—C16B—H16J141.1
C11B—C10B—C13B119.1 (2)H16H—C16B—H16J56.3
C11B—C10B—C9B120.6 (2)H16I—C16B—H16J56.3
C13B—C10B—C9B120.0 (2)N2B—C16B—H16K109.5
C17B—C18B—C19B122.3 (2)H16G—C16B—H16K56.3
C17B—C18B—O3B122.6 (2)H16H—C16B—H16K141.1
C19B—C18B—O3B115.0 (2)H16I—C16B—H16K56.3
C19B—O4B—C23B117.3 (2)H16J—C16B—H16K109.5
C21A—C22A—C17A120.5 (2)N2B—C16B—H16L109.5
C21A—C22A—H22A119.7H16G—C16B—H16L56.3
C17A—C22A—H22A119.7H16H—C16B—H16L56.3
O5B—C13B—N2B119.9 (2)H16I—C16B—H16L141.1
O5B—C13B—C10B124.5 (2)H16J—C16B—H16L109.5
N2B—C13B—C10B115.6 (2)H16K—C16B—H16L109.5
C24A—C8A—C9A112.47 (18)C21B—C22B—C17B120.2 (3)
C24A—C8A—C7A111.13 (18)C21B—C22B—H22B119.9
C9A—C8A—C7A108.06 (18)C17B—C22B—H22B119.9
C24A—C8A—H8A107.2 (13)O4A—C23A—H23A109.5
C9A—C8A—H8A110.6 (13)O4A—C23A—H23B109.5
C7A—C8A—H8A107.3 (13)H23A—C23A—H23B109.5
O2B—C24B—O3B117.7 (2)O4A—C23A—H23C109.5
O2B—C24B—C8B124.5 (2)H23A—C23A—H23C109.5
O3B—C24B—C8B117.79 (19)H23B—C23A—H23C109.5
C10B—C9B—C8B108.28 (18)C3A—C4A—C5A120.4 (3)
C10B—C9B—C17B115.05 (19)C3A—C4A—H4A119.8
C8B—C9B—C17B109.41 (18)C5A—C4A—H4A119.8
C10B—C9B—H9B108.0 (13)C2A—C3A—C4A119.7 (3)
C8B—C9B—H9B106.7 (13)C2A—C3A—H3A120.2
C17B—C9B—H9B109.1 (13)C4A—C3A—H3A120.2
O1B—C7B—C6B106.77 (18)C3A—C2A—C1A120.7 (3)
O1B—C7B—C8B108.42 (18)C3A—C2A—H2A119.7
C6B—C7B—C8B114.8 (2)C1A—C2A—H2A119.7
O1B—C7B—H7B109.9 (13)C6A—C5A—C4A120.0 (3)
C6B—C7B—H7B109.9 (13)C6A—C5A—H5A120.0
C8B—C7B—H7B107.0 (13)C4A—C5A—H5A120.0
O4A—C19A—C20A125.6 (2)C2B—C1B—C6B120.8 (3)
O4A—C19A—C18A116.1 (2)C2B—C1B—H1B119.6
C20A—C19A—C18A118.4 (2)C6B—C1B—H1B119.6
C22B—C17B—C18B118.1 (2)C2B—C3B—C4B119.4 (3)
C22B—C17B—C9B124.3 (2)C2B—C3B—H3B120.3
C18B—C17B—C9B117.61 (19)C4B—C3B—H3B120.3
O5A—C13A—N2A119.7 (2)O4B—C23B—H23D109.5
O5A—C13A—C10A124.3 (2)O4B—C23B—H23E109.5
N2A—C13A—C10A116.00 (19)H23D—C23B—H23E109.5
O1A—C7A—C6A106.58 (17)O4B—C23B—H23F109.5
O1A—C7A—C8A107.71 (17)H23D—C23B—H23F109.5
C6A—C7A—C8A116.74 (19)H23E—C23B—H23F109.5
O1A—C7A—H7A107.5 (14)N1B—C15B—H15G109.5
C6A—C7A—H7A108.4 (13)N1B—C15B—H15H109.5
C8A—C7A—H7A109.5 (14)H15G—C15B—H15H109.5
O6B—C14B—N2B122.6 (3)N1B—C15B—H15I109.5
O6B—C14B—N1B121.3 (3)H15G—C15B—H15I109.5
N2B—C14B—N1B116.0 (2)H15H—C15B—H15I109.5
C5B—C6B—C1B118.6 (2)N1B—C15B—H15J109.5
C5B—C6B—C7B122.5 (2)H15G—C15B—H15J141.1
C1B—C6B—C7B118.8 (2)H15H—C15B—H15J56.3
C22A—C21A—C20A121.0 (2)H15I—C15B—H15J56.3
C22A—C21A—H21A119.5N1B—C15B—H15K109.5
C20A—C21A—H21A119.5H15G—C15B—H15K56.3
N1A—C15A—H15A109.5H15H—C15B—H15K141.1
N1A—C15A—H15B109.5H15I—C15B—H15K56.3
H15A—C15A—H15B109.5H15J—C15B—H15K109.5
N1A—C15A—H15C109.5N1B—C15B—H15L109.5
H15A—C15A—H15C109.5H15G—C15B—H15L56.3
H15B—C15A—H15C109.5H15H—C15B—H15L56.3
N1A—C15A—H15D109.5H15I—C15B—H15L141.1
H15A—C15A—H15D141.1H15J—C15B—H15L109.5
H15B—C15A—H15D56.3H15K—C15B—H15L109.5
H15C—C15A—H15D56.3C22B—C21B—C20B121.3 (3)
N1A—C15A—H15E109.5C22B—C21B—H21B119.3
H15A—C15A—H15E56.3C20B—C21B—H21B119.3
H15B—C15A—H15E141.1C3B—C4B—C5B120.2 (3)
H15C—C15A—H15E56.3C3B—C4B—H4B119.9
H15D—C15A—H15E109.5C5B—C4B—H4B119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21A—H21A···O5Bi0.932.553.435 (4)159
C20B—H20B···O5Aii0.932.343.175 (3)149
C23B—H23D···O6Biii0.962.463.249 (4)139
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+2, y+2, z+1; (iii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC23H20N2O6
Mr420.41
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.2283 (7), 14.0584 (10), 16.4457 (13)
α, β, γ (°)94.869 (2), 102.547 (2), 105.270 (2)
V3)1986.1 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.20 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker 2004)
Tmin, Tmax0.979, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
36657, 7558, 5648
Rint0.029
(sin θ/λ)max1)0.611
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.141, 1.06
No. of reflections7558
No. of parameters588
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.18

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21A—H21A···O5Bi0.932.553.435 (4)158.5
C20B—H20B···O5Aii0.932.343.175 (3)149.2
C23B—H23D···O6Biii0.962.463.249 (4)138.9
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+2, y+2, z+1; (iii) x, y1, z.
 

Acknowledgements

SA thanks the UGC, India, for financial support

References

First citationBruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCasley-Smith, J. R., Wang, C. T., Casley-Smith, J. R. & Zi-hai, C. (1993). Br. Med. J. 307, 1037–1041.  CAS
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationGoel, R. K., Maiti, R. N., Manickam, M. & Ray, A. B. (1997). Indian J. Exp. Biol. 35, 1080–1083.  CAS PubMed
First citationHossain, C. F., Okuyama, E. & Yamazaki, M. (1996). Chem. Pharm. Bull. (Tokyo), 44, 1535–1539.  CrossRef CAS PubMed
First citationJagadeesan, G., Kannan, D., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o80.  CSD CrossRef IUCr Journals
First citationKawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., Ito, C. & Furukawa, H. (2001). Anticancer Res. 21, 1905–1911.  Web of Science PubMed CAS
First citationPavao, F., Castilho, M. S., Pupo, M. T., Dias, R. L. A., Correa, A. G., Fernandes, J. B., Da Silva, M. F. G. F., Mafezoli, J., Vieir, P. C. & Oliva, G. (2002). FEBS Lett. 520, 13–17.  Web of Science PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationSu, C. R., Yeh, S. F., Liu, C. M., Damu, A. G., Kuo, T. H., Chiang, P. C., Bastow, K. F., Lee, K. H. & Wu, T. S. (2009). Bioorg. Med. Chem. 17, 6137–6143.  Web of Science CrossRef PubMed CAS
First citationXu, Z. Q., Pupek, K., Suling, W. J., Enache, L. & Flavin, M. T. (2006). Bioorg. Med. Chem. 14, 4610–4626.  Web of Science CrossRef PubMed CAS

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 69| Part 8| August 2013| Pages o1199-o1200
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds