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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-(2-Meth­­oxy­naphthalen-1-yl)-2-benzo­furan-1(3H)-one

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com

(Received 21 June 2011; accepted 4 July 2011; online 9 July 2011)

The asymmetric unit of the title compound, C19H14O3, contains two crystallographically independent mol­ecules in which the dihedral angles between the naphthalene and benzofuran ring systems are 76.49 (7) and 86.17 (7)°. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O hydrogen-bonding inter­actions into chains running parallel to the a axis. In addition, the crystal packing is stabilized by C—H⋯π inter­actions.

Related literature

For the biological activity of benzofuran compounds, see: Howlett et al. (1999[Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283-289.]); Aslam et al. (2006[Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]). For related structures see: Thenmozhi et al. (2010[Thenmozhi, S., SubbiahPandi, A., Arulclement, J. & MohanaKrishnan, A. K. (2010). Acta Cryst. E66, o894.]); Valerga et al. (2009[Valerga, P., Puerta, M. C., Rodríguez Negrín, Z., Castañedo Cancio, N. & Palma Lovillo, M. (2009). Acta Cryst. E65, o1979.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14O3

  • Mr = 290.30

  • Monoclinic, P 21 /c

  • a = 13.2572 (5) Å

  • b = 11.8560 (4) Å

  • c = 18.6160 (7) Å

  • β = 91.657 (2)°

  • V = 2924.79 (18) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.24 × 0.22 × 0.2 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.982

  • 27565 measured reflections

  • 7292 independent reflections

  • 4519 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.122

  • S = 1.00

  • 7292 reflections

  • 399 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg4 and Cg8 are the centroids of C1–C6, C13–C18 and C20–C25 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9⋯O6i 0.93 2.45 3.238 (2) 142
C14—H14⋯O6ii 0.93 2.51 3.435 (2) 175
C12—H12⋯Cg4ii 0.98 2.93 3.755 (2) 143
C15—H15⋯Cg2iii 0.93 2.88 3.800 (2) 169
C16—H16⋯Cg8iv 0.93 2.81 3.553 (2) 137
C30—H30CCg8v 0.96 2.89 3.687 (2) 141
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z; (iii) [x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]; (iv) -x+2, -y+1, -z; (v) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Molecules containing a benzofuran ring system have attracted considerable interest in view of their biological and pharmacological properties (Howlett et al., 1999; Galal et al., 2009). Compounds with the benzofuran skeleton (Akgul & Anil, 2003) show significant pharmacological activities such as fungicidal (Aslam et al., 2006), antitumor and antiviral activities (Galal et al., 2009). In order to get detailed information such as the geometrical features and the underlying interaction of the crystal structure, an X-ray study of the title compound was carried out.

Fig. 1 shows the asymmetric unit consisting of two molecules of the title compound. The naphthalene ring system is itself planar and the benzofuran ring system is also planar with a maximum deviation of 0.039 (1), 0.008 (1) Å, respectively in one molecule and 0.022 (2), 0.033 (1) Å in the other. The dihedral angles between the naphthalene ring systems and the benzofuran ring systems are 76.49 (7) and 86.17 (7)° in the two molecules. The C7—C8—O1—C11 [179.12 (15)°] and C29—C28—O4—C30 [179.87 (140)°] torsional angles that indicate the methoxy substitutions are essentially coplanar with the attached ring.

Hydrogen bond interactions are shown in Table 1 and the C—H···π interactions (Cg2, Cg4 and Cg8 are centriods of the rings containing the atoms C1—C6, C13—C18 and C20—C25 respectively). In the crystal structure, molecules are linked by intermolecular C—H···O hydrogen-bonding interactions into chains running parallel to the a axis.

Related literature top

For the biological activity of benzofuran compounds, see: Howlett et al. (1999); Aslam et al. (2006); Galal et al. (2009). For natural products with benzofuran rings, see: Akgul & Anil (2003). For related structures see: Thenmozhi et al. (2010); Valerga et al. (2009).

Experimental top

A mixture of 2-hydrazinopyridine and tolualdehyde were refluxed in ethanol with a catalytic quantity of conc. HCl or gl. AcOH. After the reaction is over, the contents were cooled down and the resulting product was filtered off. Diffraction quality crystals were obtained upon recrystallization in ethanol.

Refinement top

The C bound H atoms positioned geometrically (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with 1.5Ueq(C) for methyl H and 1.2 Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A perspective view of the molecule showing the thermal ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. C—H···O interactions (dotted lines) in the crystal structure of the title compound. The crystal packing of the molecules is viewed down the b axis.
3-(2-Methoxynaphthalen-1-yl)-2-benzofuran-1(3H)-one top
Crystal data top
C19H14O3F(000) = 1216
Mr = 290.30Dx = 1.319 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1125 reflections
a = 13.2572 (5) Åθ = 1.5–28.3°
b = 11.8560 (4) ŵ = 0.09 mm1
c = 18.6160 (7) ÅT = 293 K
β = 91.657 (2)°Block, colourless
V = 2924.79 (18) Å30.24 × 0.22 × 0.2 mm
Z = 8
Data collection top
Bruker SMART APEXII area-detector
diffractometer
7292 independent reflections
Radiation source: fine-focus sealed tube4519 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and ϕ scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1717
Tmin = 0.979, Tmax = 0.982k = 1512
27565 measured reflectionsl = 2421
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0514P)2 + 0.4948P]
where P = (Fo2 + 2Fc2)/3
7292 reflections(Δ/σ)max = 0.001
399 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C19H14O3V = 2924.79 (18) Å3
Mr = 290.30Z = 8
Monoclinic, P21/cMo Kα radiation
a = 13.2572 (5) ŵ = 0.09 mm1
b = 11.8560 (4) ÅT = 293 K
c = 18.6160 (7) Å0.24 × 0.22 × 0.2 mm
β = 91.657 (2)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
7292 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
4519 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.982Rint = 0.027
27565 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.00Δρmax = 0.15 e Å3
7292 reflectionsΔρmin = 0.16 e Å3
399 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*/Ueq
C10.41021 (11)0.73457 (15)0.18630 (8)0.0555 (4)
H10.41910.65790.17810.067*
C20.34451 (13)0.76890 (18)0.23690 (9)0.0676 (5)
H20.30920.71510.26240.081*
C30.32915 (14)0.88307 (19)0.25124 (10)0.0734 (5)
H30.28320.90510.28540.088*
C40.38149 (14)0.96087 (17)0.21512 (10)0.0691 (5)
H40.37181.03690.22510.083*
C50.45096 (11)0.92985 (14)0.16230 (8)0.0518 (4)
C60.46531 (10)0.81381 (12)0.14591 (7)0.0438 (3)
C70.53569 (10)0.78300 (12)0.09255 (8)0.0428 (3)
C80.59224 (10)0.86679 (13)0.06143 (8)0.0477 (4)
C90.57635 (12)0.98140 (14)0.07692 (9)0.0560 (4)
H90.61291.03670.05360.067*
C100.50777 (13)1.01078 (14)0.12582 (10)0.0604 (4)
H100.49781.08680.13570.072*
C110.72638 (15)0.91029 (19)0.01797 (12)0.0838 (6)
H11A0.68430.96100.04570.126*
H11B0.77100.87140.04930.126*
H11C0.76530.95230.01710.126*
C120.55068 (10)0.66110 (12)0.07285 (8)0.0459 (3)
H120.49060.61890.08650.055*
C130.57246 (10)0.63310 (12)0.00365 (8)0.0450 (3)
C140.51875 (12)0.65709 (14)0.06670 (9)0.0597 (4)
H140.45730.69480.06640.072*
C150.56080 (16)0.62235 (16)0.13052 (10)0.0711 (5)
H150.52690.63810.17380.085*
C160.65141 (15)0.56512 (16)0.13148 (10)0.0689 (5)
H160.67770.54370.17520.083*
C170.70303 (13)0.53953 (14)0.06901 (9)0.0587 (4)
H170.76350.49990.06930.070*
C180.66194 (10)0.57481 (12)0.00517 (8)0.0460 (3)
C190.70285 (11)0.56471 (13)0.06827 (9)0.0514 (4)
O10.66568 (8)0.83143 (10)0.01706 (7)0.0691 (3)
O20.63802 (8)0.61512 (9)0.11334 (5)0.0532 (3)
O30.77989 (9)0.52232 (11)0.09071 (7)0.0748 (4)
C201.22184 (12)0.35822 (17)0.29788 (9)0.0630 (5)
H201.27030.32330.32740.076*
C211.20853 (13)0.47138 (18)0.30274 (9)0.0662 (5)
H211.24750.51370.33520.079*
C221.13564 (13)0.52358 (15)0.25850 (9)0.0599 (4)
H221.12680.60130.26140.072*
C231.07740 (12)0.46323 (13)0.21134 (8)0.0521 (4)
H231.02910.50050.18290.063*
C241.08833 (10)0.34463 (12)0.20421 (7)0.0438 (3)
C251.16370 (11)0.29228 (14)0.24895 (8)0.0498 (4)
C261.17846 (12)0.17547 (15)0.24275 (9)0.0592 (4)
H261.22660.14060.27250.071*
C271.12480 (12)0.11230 (14)0.19494 (9)0.0578 (4)
H271.13720.03530.19140.069*
C281.05014 (11)0.16302 (13)0.15056 (8)0.0479 (4)
C291.03008 (10)0.27724 (12)0.15521 (7)0.0426 (3)
C301.01050 (15)0.01427 (14)0.09473 (10)0.0672 (5)
H30A1.07800.02640.07920.101*
H30B0.96340.04550.06000.101*
H30C1.00210.05040.14030.101*
C310.94556 (10)0.32783 (12)0.10989 (8)0.0438 (3)
H310.94360.40900.11960.053*
C320.94656 (11)0.31139 (12)0.03025 (8)0.0470 (3)
C331.02020 (14)0.33418 (15)0.01830 (9)0.0654 (5)
H331.08260.36310.00350.079*
C340.9977 (2)0.31242 (18)0.08992 (11)0.0870 (7)
H341.04640.32600.12390.104*
C350.9044 (2)0.27095 (18)0.11231 (11)0.0908 (7)
H350.89110.25830.16100.109*
C360.83122 (17)0.24824 (15)0.06370 (11)0.0753 (6)
H360.76840.22030.07840.090*
C370.85471 (12)0.26858 (13)0.00780 (9)0.0529 (4)
C380.79453 (12)0.24820 (13)0.07115 (10)0.0570 (4)
O40.99266 (9)0.10388 (9)0.10173 (6)0.0598 (3)
O50.84930 (7)0.27923 (9)0.13030 (6)0.0530 (3)
O60.71107 (9)0.20914 (12)0.07622 (9)0.0861 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0534 (8)0.0582 (10)0.0553 (9)0.0061 (7)0.0103 (7)0.0071 (8)
C20.0605 (10)0.0846 (14)0.0585 (11)0.0090 (9)0.0161 (8)0.0075 (9)
C30.0623 (10)0.0955 (16)0.0631 (11)0.0115 (10)0.0165 (9)0.0168 (11)
C40.0679 (11)0.0690 (12)0.0706 (12)0.0218 (9)0.0060 (9)0.0158 (10)
C50.0497 (8)0.0514 (10)0.0540 (9)0.0090 (7)0.0053 (7)0.0058 (7)
C60.0383 (7)0.0485 (9)0.0446 (8)0.0014 (6)0.0024 (6)0.0043 (7)
C70.0382 (7)0.0436 (8)0.0466 (8)0.0014 (6)0.0014 (6)0.0033 (6)
C80.0431 (7)0.0516 (9)0.0484 (8)0.0047 (6)0.0024 (6)0.0012 (7)
C90.0593 (9)0.0454 (10)0.0630 (10)0.0071 (7)0.0045 (8)0.0061 (8)
C100.0675 (10)0.0441 (10)0.0692 (11)0.0072 (8)0.0053 (9)0.0030 (8)
C110.0716 (12)0.0976 (16)0.0834 (14)0.0200 (11)0.0234 (10)0.0152 (12)
C120.0412 (7)0.0451 (9)0.0519 (9)0.0031 (6)0.0086 (6)0.0031 (7)
C130.0439 (7)0.0404 (8)0.0507 (8)0.0045 (6)0.0027 (6)0.0043 (7)
C140.0568 (9)0.0568 (11)0.0648 (11)0.0010 (8)0.0115 (8)0.0046 (8)
C150.0952 (14)0.0686 (12)0.0487 (10)0.0125 (11)0.0121 (9)0.0042 (9)
C160.0913 (13)0.0648 (12)0.0513 (10)0.0121 (10)0.0165 (9)0.0106 (9)
C170.0616 (9)0.0530 (10)0.0626 (11)0.0007 (8)0.0179 (8)0.0075 (8)
C180.0473 (7)0.0413 (8)0.0496 (8)0.0015 (6)0.0068 (6)0.0016 (7)
C190.0528 (8)0.0424 (9)0.0590 (10)0.0047 (7)0.0019 (7)0.0028 (7)
O10.0654 (7)0.0627 (8)0.0810 (8)0.0175 (6)0.0313 (6)0.0063 (6)
O20.0633 (6)0.0513 (7)0.0452 (6)0.0078 (5)0.0023 (5)0.0023 (5)
O30.0693 (8)0.0728 (9)0.0817 (9)0.0253 (6)0.0110 (6)0.0048 (7)
C200.0580 (9)0.0837 (14)0.0467 (9)0.0084 (9)0.0081 (7)0.0004 (9)
C210.0659 (10)0.0841 (14)0.0485 (10)0.0049 (9)0.0033 (8)0.0093 (9)
C220.0696 (10)0.0568 (11)0.0535 (10)0.0023 (8)0.0024 (8)0.0047 (8)
C230.0569 (9)0.0504 (10)0.0489 (9)0.0041 (7)0.0015 (7)0.0031 (7)
C240.0441 (7)0.0480 (9)0.0395 (8)0.0051 (6)0.0071 (6)0.0056 (6)
C250.0473 (8)0.0619 (11)0.0404 (8)0.0101 (7)0.0036 (6)0.0051 (7)
C260.0572 (9)0.0678 (12)0.0524 (9)0.0226 (8)0.0029 (7)0.0102 (8)
C270.0640 (9)0.0488 (10)0.0608 (10)0.0201 (8)0.0034 (8)0.0085 (8)
C280.0518 (8)0.0446 (9)0.0473 (8)0.0074 (7)0.0042 (7)0.0040 (7)
C290.0435 (7)0.0415 (8)0.0429 (8)0.0075 (6)0.0037 (6)0.0062 (6)
C300.0928 (13)0.0409 (10)0.0685 (11)0.0084 (9)0.0117 (10)0.0036 (8)
C310.0419 (7)0.0379 (8)0.0516 (9)0.0027 (6)0.0015 (6)0.0049 (6)
C320.0528 (8)0.0382 (8)0.0501 (8)0.0079 (6)0.0001 (7)0.0091 (7)
C330.0729 (11)0.0626 (12)0.0615 (11)0.0085 (9)0.0119 (9)0.0202 (9)
C340.1293 (19)0.0723 (14)0.0608 (13)0.0321 (13)0.0279 (13)0.0245 (10)
C350.160 (2)0.0598 (13)0.0514 (12)0.0322 (14)0.0157 (14)0.0026 (10)
C360.1050 (15)0.0499 (11)0.0690 (13)0.0135 (10)0.0301 (12)0.0001 (9)
C370.0610 (9)0.0383 (8)0.0587 (10)0.0085 (7)0.0127 (8)0.0035 (7)
C380.0469 (8)0.0427 (9)0.0810 (12)0.0037 (7)0.0056 (8)0.0076 (8)
O40.0742 (7)0.0388 (6)0.0659 (7)0.0071 (5)0.0074 (6)0.0018 (5)
O50.0443 (5)0.0545 (7)0.0605 (7)0.0050 (5)0.0063 (5)0.0078 (5)
O60.0511 (7)0.0750 (9)0.1318 (13)0.0123 (6)0.0054 (7)0.0109 (8)
Geometric parameters (Å, º) top
C1—C21.363 (2)C20—C211.356 (3)
C1—C61.419 (2)C20—C251.412 (2)
C1—H10.9300C20—H200.9300
C2—C31.396 (3)C21—C221.396 (2)
C2—H20.9300C21—H210.9300
C3—C41.346 (3)C22—C231.356 (2)
C3—H30.9300C22—H220.9300
C4—C51.415 (2)C23—C241.420 (2)
C4—H40.9300C23—H230.9300
C5—C101.407 (2)C24—C291.423 (2)
C5—C61.423 (2)C24—C251.4245 (19)
C6—C71.4298 (19)C25—C261.404 (2)
C7—C81.382 (2)C26—C271.350 (2)
C7—C121.506 (2)C26—H260.9300
C8—O11.3611 (18)C27—C281.406 (2)
C8—C91.406 (2)C27—H270.9300
C9—C101.351 (2)C28—O41.3633 (18)
C9—H90.9300C28—C291.383 (2)
C10—H100.9300C29—C311.5075 (19)
C11—O11.406 (2)C30—O41.4272 (18)
C11—H11A0.9600C30—H30A0.9600
C11—H11B0.9600C30—H30B0.9600
C11—H11C0.9600C30—H30C0.9600
C12—O21.4681 (17)C31—O51.4604 (16)
C12—C131.499 (2)C31—C321.496 (2)
C12—H120.9800C31—H310.9800
C13—C181.374 (2)C32—C371.373 (2)
C13—C141.385 (2)C32—C331.376 (2)
C14—C151.389 (2)C33—C341.382 (3)
C14—H140.9300C33—H330.9300
C15—C161.380 (3)C34—C351.384 (3)
C15—H150.9300C34—H340.9300
C16—C171.366 (3)C35—C361.372 (3)
C16—H160.9300C35—H350.9300
C17—C181.386 (2)C36—C371.379 (2)
C17—H170.9300C36—H360.9300
C18—C191.461 (2)C37—C381.463 (2)
C19—O31.2023 (18)C38—O61.2057 (19)
C19—O21.3570 (18)C38—O51.352 (2)
C2—C1—C6121.16 (16)C21—C20—C25121.40 (15)
C2—C1—H1119.4C21—C20—H20119.3
C6—C1—H1119.4C25—C20—H20119.3
C1—C2—C3121.42 (18)C20—C21—C22119.22 (16)
C1—C2—H2119.3C20—C21—H21120.4
C3—C2—H2119.3C22—C21—H21120.4
C4—C3—C2119.27 (17)C23—C22—C21121.29 (17)
C4—C3—H3120.4C23—C22—H22119.4
C2—C3—H3120.4C21—C22—H22119.4
C3—C4—C5121.62 (17)C22—C23—C24121.67 (15)
C3—C4—H4119.2C22—C23—H23119.2
C5—C4—H4119.2C24—C23—H23119.2
C10—C5—C4121.77 (16)C23—C24—C29124.11 (13)
C10—C5—C6118.63 (14)C23—C24—C25116.65 (13)
C4—C5—C6119.60 (16)C29—C24—C25119.24 (13)
C1—C6—C5116.90 (13)C26—C25—C20121.63 (14)
C1—C6—C7123.73 (14)C26—C25—C24118.61 (14)
C5—C6—C7119.33 (13)C20—C25—C24119.76 (15)
C8—C7—C6118.71 (13)C27—C26—C25121.96 (14)
C8—C7—C12120.73 (13)C27—C26—H26119.0
C6—C7—C12120.51 (12)C25—C26—H26119.0
O1—C8—C7116.06 (14)C26—C27—C28119.92 (15)
O1—C8—C9122.42 (14)C26—C27—H27120.0
C7—C8—C9121.50 (14)C28—C27—H27120.0
C10—C9—C8119.68 (15)O4—C28—C29116.14 (12)
C10—C9—H9120.2O4—C28—C27122.84 (14)
C8—C9—H9120.2C29—C28—C27121.02 (15)
C9—C10—C5121.98 (16)C28—C29—C24119.20 (12)
C9—C10—H10119.0C28—C29—C31119.71 (13)
C5—C10—H10119.0C24—C29—C31121.06 (12)
O1—C11—H11A109.5O4—C30—H30A109.5
O1—C11—H11B109.5O4—C30—H30B109.5
H11A—C11—H11B109.5H30A—C30—H30B109.5
O1—C11—H11C109.5O4—C30—H30C109.5
H11A—C11—H11C109.5H30A—C30—H30C109.5
H11B—C11—H11C109.5H30B—C30—H30C109.5
O2—C12—C13103.58 (11)O5—C31—C32103.85 (11)
O2—C12—C7109.82 (11)O5—C31—C29109.78 (11)
C13—C12—C7118.33 (12)C32—C31—C29118.36 (12)
O2—C12—H12108.2O5—C31—H31108.1
C13—C12—H12108.2C32—C31—H31108.1
C7—C12—H12108.2C29—C31—H31108.1
C18—C13—C14120.59 (14)C37—C32—C33120.82 (15)
C18—C13—C12108.74 (13)C37—C32—C31108.46 (13)
C14—C13—C12130.67 (14)C33—C32—C31130.70 (15)
C13—C14—C15117.05 (16)C32—C33—C34117.35 (19)
C13—C14—H14121.5C32—C33—H33121.3
C15—C14—H14121.5C34—C33—H33121.3
C16—C15—C14121.85 (17)C33—C34—C35121.5 (2)
C16—C15—H15119.1C33—C34—H34119.2
C14—C15—H15119.1C35—C34—H34119.2
C17—C16—C15120.85 (16)C36—C35—C34120.91 (19)
C17—C16—H16119.6C36—C35—H35119.5
C15—C16—H16119.6C34—C35—H35119.5
C16—C17—C18117.59 (16)C35—C36—C37117.3 (2)
C16—C17—H17121.2C35—C36—H36121.4
C18—C17—H17121.2C37—C36—H36121.4
C13—C18—C17122.04 (15)C32—C37—C36122.13 (18)
C13—C18—C19108.61 (13)C32—C37—C38108.36 (14)
C17—C18—C19129.28 (14)C36—C37—C38129.49 (17)
O3—C19—O2121.07 (15)O6—C38—O5120.88 (17)
O3—C19—C18130.39 (15)O6—C38—C37130.50 (17)
O2—C19—C18108.53 (12)O5—C38—C37108.61 (13)
C8—O1—C11120.37 (14)C28—O4—C30118.35 (13)
C19—O2—C12110.51 (11)C38—O5—C31110.37 (12)
C6—C1—C2—C30.3 (3)C25—C20—C21—C220.1 (3)
C1—C2—C3—C41.0 (3)C20—C21—C22—C230.6 (3)
C2—C3—C4—C50.7 (3)C21—C22—C23—C240.6 (2)
C3—C4—C5—C10178.27 (17)C22—C23—C24—C29179.37 (14)
C3—C4—C5—C60.9 (3)C22—C23—C24—C250.2 (2)
C2—C1—C6—C51.9 (2)C21—C20—C25—C26178.79 (16)
C2—C1—C6—C7179.56 (15)C21—C20—C25—C240.9 (2)
C10—C5—C6—C1177.05 (14)C23—C24—C25—C26178.81 (14)
C4—C5—C6—C12.1 (2)C29—C24—C25—C260.4 (2)
C10—C5—C6—C70.8 (2)C23—C24—C25—C200.9 (2)
C4—C5—C6—C7179.93 (14)C29—C24—C25—C20179.88 (13)
C1—C6—C7—C8173.84 (13)C20—C25—C26—C27178.43 (16)
C5—C6—C7—C83.8 (2)C24—C25—C26—C271.2 (2)
C1—C6—C7—C123.8 (2)C25—C26—C27—C281.3 (3)
C5—C6—C7—C12178.57 (12)C26—C27—C28—O4179.32 (15)
C6—C7—C8—O1172.94 (12)C26—C27—C28—C290.3 (2)
C12—C7—C8—O14.7 (2)O4—C28—C29—C24178.96 (12)
C6—C7—C8—C95.1 (2)C27—C28—C29—C242.0 (2)
C12—C7—C8—C9177.31 (13)O4—C28—C29—C312.57 (19)
O1—C8—C9—C10174.67 (15)C27—C28—C29—C31176.51 (13)
C7—C8—C9—C103.2 (2)C23—C24—C29—C28177.19 (14)
C8—C9—C10—C50.0 (2)C25—C24—C29—C282.0 (2)
C4—C5—C10—C9177.98 (16)C23—C24—C29—C314.4 (2)
C6—C5—C10—C91.2 (2)C25—C24—C29—C31176.45 (12)
C8—C7—C12—O281.43 (16)C28—C29—C31—O563.33 (17)
C6—C7—C12—O296.15 (14)C24—C29—C31—O5115.11 (14)
C8—C7—C12—C1337.12 (19)C28—C29—C31—C3255.56 (18)
C6—C7—C12—C13145.30 (13)C24—C29—C31—C32126.00 (14)
O2—C12—C13—C181.35 (15)O5—C31—C32—C375.82 (15)
C7—C12—C13—C18123.12 (14)C29—C31—C32—C37127.76 (14)
O2—C12—C13—C14178.30 (15)O5—C31—C32—C33175.73 (15)
C7—C12—C13—C1456.5 (2)C29—C31—C32—C3353.8 (2)
C18—C13—C14—C151.7 (2)C37—C32—C33—C340.1 (2)
C12—C13—C14—C15177.97 (15)C31—C32—C33—C34178.20 (16)
C13—C14—C15—C160.8 (3)C32—C33—C34—C350.9 (3)
C14—C15—C16—C170.6 (3)C33—C34—C35—C361.0 (3)
C15—C16—C17—C181.1 (3)C34—C35—C36—C370.1 (3)
C14—C13—C18—C171.2 (2)C33—C32—C37—C361.1 (2)
C12—C13—C18—C17178.54 (14)C31—C32—C37—C36177.56 (14)
C14—C13—C18—C19178.39 (14)C33—C32—C37—C38177.33 (14)
C12—C13—C18—C191.31 (16)C31—C32—C37—C384.03 (16)
C16—C17—C18—C130.3 (2)C35—C36—C37—C321.0 (2)
C16—C17—C18—C19176.36 (16)C35—C36—C37—C38177.07 (17)
C13—C18—C19—O3178.41 (17)C32—C37—C38—O6178.17 (17)
C17—C18—C19—O31.4 (3)C36—C37—C38—O60.1 (3)
C13—C18—C19—O20.74 (17)C32—C37—C38—O50.50 (17)
C17—C18—C19—O2177.71 (15)C36—C37—C38—O5178.75 (15)
C7—C8—O1—C11179.12 (15)C29—C28—O4—C30179.87 (14)
C9—C8—O1—C112.9 (2)C27—C28—O4—C301.1 (2)
O3—C19—O2—C12179.41 (14)O6—C38—O5—C31177.81 (14)
C18—C19—O2—C120.16 (16)C37—C38—O5—C313.38 (16)
C13—C12—O2—C190.90 (15)C32—C31—O5—C385.60 (14)
C7—C12—O2—C19128.20 (12)C29—C31—O5—C38133.08 (12)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg4 and Cg8 are the centroids of C1–C6, C13–C18 and C20–C25 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9···O6i0.932.453.238 (2)142
C14—H14···O6ii0.932.513.435 (2)175
C12—H12···Cg4ii0.982.933.755 (2)143
C15—H15···Cg2iii0.932.883.800 (2)169
C16—H16···Cg8iv0.932.813.553 (2)137
C30—H30C···Cg8v0.962.893.687 (2)141
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x, y+1/2, z3/2; (iv) x+2, y+1, z; (v) x+2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H14O3
Mr290.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.2572 (5), 11.8560 (4), 18.6160 (7)
β (°) 91.657 (2)
V3)2924.79 (18)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.24 × 0.22 × 0.2
Data collection
DiffractometerBruker SMART APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.979, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
27565, 7292, 4519
Rint0.027
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.122, 1.00
No. of reflections7292
No. of parameters399
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.16

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg2, Cg4 and Cg8 are the centroids of C1–C6, C13–C18 and C20–C25 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9···O6i0.932.453.238 (2)142
C14—H14···O6ii0.932.513.435 (2)175
C12—H12···Cg4ii0.982.933.755 (2)143
C15—H15···Cg2iii0.932.883.800 (2)169
C16—H16···Cg8iv0.932.813.553 (2)137
C30—H30C···Cg8v0.962.893.687 (2)141
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x, y+1/2, z3/2; (iv) x+2, y+1, z; (v) x+2, y1/2, z+1/2.
 

Acknowledgements

SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC&SAP) for financial support.

References

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