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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-Methyl 2-[(2-formyl-6-meth­­oxy­phen­­oxy)meth­yl]-3-phenyl­acrylate

aPost Graduate & Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 3 December 2011; accepted 17 December 2011; online 23 December 2011)

The title compound, C19H18O5, crystallizes with two independent mol­ecules (A and B) in an asymmetric unit in both of which the two aromatic rings are in a bis­ectional orientation as evidenced by the dihedral angle between them [41.7 (1)° in mol­ecule A and 35.6 (1)° in mol­ecule B]. Both mol­ecules adopt an E configuration with respect to the C=C bond. An intra­molecular C—H⋯O hydrogen-bond occurs in mol­ecule A. The crystal packing features inter­molecular C—H⋯O inter­actions.

Related literature

For background to the synthesis, see: Bakthadoss et al. (2009[Bakthadoss, M., Sivakumar, G. & Kannan, D. (2009). Org. Lett. 11, 4466-4469.]). For related phenyl acrylate compounds, see: Wang et al. (2006[Wang, X.-B. & Kong, L.-Y. (2006). Acta Cryst. E62, o4558-o4559.]); Jones & Jäger (2003[Jones, P. G. & Jäger, S. (2003). Acta Cryst. E59, o369-o371.]). For their biological properties, see: Kim et al. (2004[Kim, J. H., Campbell, B. C., Mahomey, N. E., Chan, K. L. & Molyneux, R. J. (2004). J. Agric. Food Chem. 52, 7814-7821.]); Zhu et al. (2000[Zhu, J., Zhu, H., Kobamoto, N., Yasuda, M. & Tawata, S. (2000). J. Pestic. Sci. 25, 263-266.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18O5

  • Mr = 326.33

  • Triclinic, [P \overline 1]

  • a = 8.4696 (5) Å

  • b = 12.1662 (7) Å

  • c = 16.9860 (9) Å

  • α = 94.423 (3)°

  • β = 100.038 (3)°

  • γ = 103.475 (3)°

  • V = 1663.33 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • 30114 measured reflections

  • 8303 independent reflections

  • 5258 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.137

  • S = 0.93

  • 8303 reflections

  • 433 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 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
C17A—H17A⋯O2A 0.93 2.48 3.354 (2) 156
C9A—H9A1⋯O4Bi 0.97 2.55 3.2215 (16) 126
C19B—H19D⋯O5Aii 0.96 2.43 3.275 (3) 147
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., 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, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Methyl cinnamate is used widely due to its flavour and fragrance in productions of cosmetics, beverages, baked goods, and convenience foods (Kim et al., 2004). Cinnamic acid exhibits higher antifungal activity against Asperigillus niger, comparing to that of miconazole and a significant antifungal effect against A. flavus and A. terreus, while caffeic acid was inactive to the antifungal activity (Zhu et al., 2000). In view of this medicinal importance, the crystal structure determination of the title compound was carried out and the results are presented here.

The asymmetric unit of the title compound contains the two independent molecules, A and B (Fig. 1). The dihedral angle between the C1 – C6 and C10 – C15 benzene rings is 41.7 (1)° in molecule A whereas it is 35.6 (1)° in molecule B. Both the molecules adopt E configurations with respect to the C C bond. The methoxy and formyl group at the meta positions of the benzene group are close to being coplanar with the ring (5.7 (1)° and 4.2 (1)° in molecule A and 1.5 (1)° and 2.3 (1)° in molecule B). The central unit(C8/C9/C10/O4) is equatorial with respect to the phenylacrylate and formyl-methoxyphenyoxy (C1- C8/C18/C19/O1/O2 = 78.5 (1)° and C10 – C17/O3/O5 =69.5 (1)° in molecule A and 78.3 (1)° and 61.3 (2)° in molecule B). The acrylate group in molecule A is +syn periplanar with respect to central unit (C9/C8/C18/O2 = 2.7 (1)°) whereas in molecule B, the acrylate group is –antiperiplanar with respect to the central unit (C9/C8/C18/O2 = 176.7 (2)°) as evidenced by torsion angles.

The crystal packing is stabilised by intramolecular and intermolecular C — H··· O hydrogen bond interactions (Table 1, Fig. 2).

Related literature top

For background to the synthesis, see: Bakthadoss et al. (2009). For related phenyl acrylate compounds, see: Wang et al. (2006); Jones et al. (2003). For their biological properties, see: Kim et al. (2004); Zhu et al. (2000).

Experimental top

A solution of 2-hydroxy-3-methoxybenzaldehyde(1.0 mmol, 0.152 g) and potassium carbonate (2.0 mmol, 0.2293 g) in acetonitrile solvent (5 mL) was stirred for 15 m at room temperature. To this solution, (Z)-methyl-2-(bromomethyl)-3-phenylacrylate(1.2 mmol, 0.25 g) was added drop wise. After the completion of the reaction, as indicated by TLC, acetonitrile was evaporated. EtOAc (15 mL) and water (15 mL) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product, which was purified through pad of silica gel (100–200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colourless solid (0.31 g, 95% yield). Recrystallization was carried out using ethylacetate as a solvent.

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å and Uiso(H) = 1.5Ueq(C) for methylH atoms and 1.2Ueq(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), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing of (I) with hydrogen bonds (dashed lines).
(E)-Methyl 2-[(2-formyl-6-methoxyphenoxy)methyl]-3-phenylacrylate top
Crystal data top
C19H18O5Z = 4
Mr = 326.33F(000) = 688
Triclinic, P1Dx = 1.303 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4696 (5) ÅCell parameters from 8303 reflections
b = 12.1662 (7) Åθ = 1.2–28.4°
c = 16.9860 (9) ŵ = 0.09 mm1
α = 94.423 (3)°T = 293 K
β = 100.038 (3)°Block, colourless
γ = 103.475 (3)°0.20 × 0.20 × 0.20 mm
V = 1663.33 (16) Å3
Data collection top
Bruker SMART APEXII area-detector
diffractometer
5258 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 28.4°, θmin = 1.2°
ω and ϕ scansh = 1111
30114 measured reflectionsk = 1616
8303 independent reflectionsl = 2122
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0725P)2 + 0.2552P]
where P = (Fo2 + 2Fc2)/3
8303 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C19H18O5γ = 103.475 (3)°
Mr = 326.33V = 1663.33 (16) Å3
Triclinic, P1Z = 4
a = 8.4696 (5) ÅMo Kα radiation
b = 12.1662 (7) ŵ = 0.09 mm1
c = 16.9860 (9) ÅT = 293 K
α = 94.423 (3)°0.20 × 0.20 × 0.20 mm
β = 100.038 (3)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
5258 reflections with I > 2σ(I)
30114 measured reflectionsRint = 0.032
8303 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 0.93Δρmax = 0.17 e Å3
8303 reflectionsΔρmin = 0.18 e Å3
433 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
O1A0.41536 (13)0.75129 (9)0.88919 (6)0.0567 (3)
O2A0.18473 (14)0.61117 (9)0.85240 (7)0.0611 (3)
O3A0.05209 (15)0.66404 (10)0.52848 (7)0.0641 (3)
O4A0.10199 (11)0.59456 (8)0.65973 (6)0.0449 (2)
O5A0.0729 (2)0.29588 (11)0.73737 (9)0.0909 (5)
C1A0.2947 (2)0.85775 (14)0.60506 (10)0.0600 (4)
H1A0.26510.77870.59510.072*
C2A0.2924 (3)0.92180 (17)0.54131 (11)0.0724 (5)
H2A0.26210.88550.48870.087*
C3A0.3346 (3)1.03855 (17)0.55494 (12)0.0740 (5)
H3A0.33221.08120.51180.089*
C4A0.3800 (3)1.09178 (16)0.63207 (12)0.0733 (5)
H4A0.40771.17090.64140.088*
C5A0.3851 (2)1.02901 (14)0.69644 (10)0.0630 (4)
H5A0.41851.06610.74880.076*
C6A0.34062 (19)0.91055 (13)0.68349 (9)0.0490 (3)
C7A0.34918 (18)0.84624 (12)0.75324 (9)0.0473 (3)
H7A0.43840.87650.79570.057*
C8A0.24490 (17)0.74965 (12)0.76346 (8)0.0417 (3)
C9A0.08546 (17)0.69396 (12)0.70716 (8)0.0432 (3)
H9A10.00120.67150.73760.052*
H9A20.05430.74740.67170.052*
C10A0.04856 (17)0.52761 (12)0.61780 (8)0.0455 (3)
C11A0.11578 (19)0.42426 (13)0.64278 (9)0.0512 (4)
C12A0.2642 (2)0.35353 (15)0.59765 (12)0.0664 (5)
H12A0.30940.28360.61380.080*
C13A0.3422 (2)0.38740 (18)0.53019 (12)0.0732 (5)
H13A0.44050.34020.50030.088*
C14A0.2767 (2)0.49130 (17)0.50553 (10)0.0660 (5)
H14A0.33220.51360.45970.079*
C15A0.12979 (19)0.56217 (14)0.54836 (9)0.0523 (4)
C16A0.1390 (3)0.71142 (19)0.46640 (11)0.0779 (6)
H16A0.07060.78300.45860.117*
H16B0.23870.72320.48130.117*
H16C0.16670.66020.41730.117*
C17A0.0340 (2)0.38920 (14)0.71684 (11)0.0613 (4)
H17A0.05370.44270.75000.074*
C18A0.27580 (17)0.69571 (12)0.83820 (8)0.0436 (3)
C19A0.4474 (2)0.70544 (17)0.96434 (10)0.0729 (5)
H19A0.54960.75070.99680.109*
H19B0.45530.62840.95390.109*
H19C0.35860.70670.99240.109*
O1B1.29774 (17)1.18987 (11)1.37809 (7)0.0731 (4)
O2B1.1832 (2)1.06673 (10)1.26819 (7)0.0812 (4)
O3B1.12347 (15)1.32548 (10)1.01612 (7)0.0654 (3)
O4B1.04928 (12)1.21083 (8)1.14210 (5)0.0453 (2)
O5B0.7023 (2)0.91721 (12)1.11274 (8)0.0979 (5)
C1B1.2973 (2)1.49121 (13)1.18301 (9)0.0533 (4)
H1B1.19231.44221.16660.064*
C2B1.3363 (2)1.59176 (14)1.15034 (11)0.0637 (4)
H2B1.25671.61061.11250.076*
C3B1.4919 (2)1.66485 (15)1.17302 (11)0.0667 (5)
H3B1.51721.73261.15060.080*
C4B1.6089 (2)1.63690 (15)1.22894 (11)0.0685 (5)
H4B1.71451.68541.24400.082*
C5B1.5709 (2)1.53742 (14)1.26295 (10)0.0587 (4)
H5B1.65091.52001.30140.070*
C6B1.41469 (18)1.46261 (12)1.24054 (8)0.0460 (3)
C7B1.37621 (18)1.36008 (13)1.28042 (9)0.0473 (3)
H7B1.41891.36921.33550.057*
C8B1.28832 (17)1.25531 (12)1.24876 (8)0.0435 (3)
C9B1.22565 (18)1.21970 (13)1.16011 (8)0.0447 (3)
H9B11.28221.27541.12990.054*
H9B21.24701.14681.14490.054*
C10B0.96683 (17)1.16893 (12)1.06435 (8)0.0426 (3)
C11B0.84002 (18)1.06988 (12)1.05216 (9)0.0476 (3)
C12B0.7411 (2)1.03311 (14)0.97533 (10)0.0594 (4)
H12B0.65340.96850.96730.071*
C13B0.7728 (2)1.09160 (15)0.91246 (10)0.0632 (4)
H13B0.70691.06620.86160.076*
C14B0.9019 (2)1.18846 (14)0.92324 (9)0.0577 (4)
H14B0.92391.22660.87940.069*
C15B0.99822 (19)1.22864 (12)0.99897 (9)0.0484 (3)
C16B1.1582 (3)1.38958 (19)0.95210 (12)0.0898 (7)
H16D1.24851.45520.97230.135*
H16E1.06191.41360.92910.135*
H16F1.18791.34330.91150.135*
C17B0.8112 (2)1.00228 (14)1.11870 (10)0.0616 (4)
H17B0.88181.02701.16850.074*
C18B1.2594 (2)1.16990 (13)1.30624 (9)0.0508 (4)
C19B1.1463 (4)0.97776 (18)1.31915 (15)0.1193 (10)
H19D1.09180.90681.28610.179*
H19E1.07520.99671.35350.179*
H19F1.24750.97081.35160.179*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0527 (6)0.0632 (7)0.0429 (6)0.0024 (5)0.0035 (5)0.0188 (5)
O2A0.0648 (7)0.0522 (6)0.0551 (6)0.0041 (5)0.0021 (5)0.0186 (5)
O3A0.0669 (7)0.0720 (8)0.0502 (6)0.0178 (6)0.0018 (5)0.0172 (6)
O4A0.0418 (5)0.0463 (5)0.0446 (5)0.0123 (4)0.0035 (4)0.0019 (4)
O5A0.1161 (12)0.0530 (8)0.0974 (10)0.0087 (7)0.0142 (9)0.0254 (7)
C1A0.0791 (11)0.0507 (9)0.0529 (9)0.0140 (8)0.0204 (8)0.0130 (7)
C2A0.1036 (15)0.0701 (12)0.0463 (9)0.0214 (11)0.0194 (9)0.0151 (8)
C3A0.1022 (15)0.0667 (12)0.0617 (11)0.0232 (11)0.0262 (10)0.0313 (9)
C4A0.0986 (14)0.0498 (10)0.0734 (12)0.0122 (9)0.0245 (11)0.0219 (9)
C5A0.0776 (12)0.0507 (9)0.0545 (10)0.0029 (8)0.0117 (8)0.0118 (7)
C6A0.0506 (8)0.0481 (8)0.0485 (8)0.0096 (7)0.0106 (7)0.0149 (7)
C7A0.0479 (8)0.0472 (8)0.0441 (8)0.0081 (6)0.0054 (6)0.0104 (6)
C8A0.0442 (7)0.0427 (7)0.0391 (7)0.0130 (6)0.0067 (6)0.0074 (6)
C9A0.0438 (7)0.0449 (8)0.0411 (7)0.0132 (6)0.0061 (6)0.0054 (6)
C10A0.0431 (8)0.0487 (8)0.0427 (8)0.0122 (6)0.0059 (6)0.0020 (6)
C11A0.0519 (9)0.0473 (8)0.0529 (9)0.0099 (7)0.0128 (7)0.0013 (7)
C12A0.0603 (10)0.0566 (10)0.0731 (12)0.0009 (8)0.0139 (9)0.0068 (9)
C13A0.0512 (10)0.0788 (13)0.0739 (13)0.0029 (9)0.0000 (9)0.0163 (10)
C14A0.0551 (10)0.0851 (13)0.0510 (10)0.0198 (9)0.0040 (8)0.0066 (9)
C15A0.0522 (9)0.0604 (10)0.0436 (8)0.0167 (7)0.0061 (7)0.0009 (7)
C16A0.0868 (14)0.0971 (15)0.0559 (11)0.0384 (12)0.0037 (9)0.0244 (10)
C17A0.0712 (11)0.0468 (9)0.0646 (10)0.0111 (8)0.0141 (8)0.0083 (8)
C18A0.0457 (8)0.0426 (8)0.0414 (7)0.0092 (6)0.0074 (6)0.0064 (6)
C19A0.0722 (11)0.0837 (13)0.0488 (10)0.0002 (10)0.0074 (8)0.0276 (9)
O1B0.1041 (10)0.0693 (8)0.0423 (7)0.0151 (7)0.0101 (6)0.0163 (6)
O2B0.1318 (12)0.0456 (7)0.0557 (7)0.0084 (7)0.0048 (7)0.0166 (6)
O3B0.0734 (8)0.0593 (7)0.0506 (6)0.0068 (6)0.0032 (5)0.0218 (5)
O4B0.0458 (5)0.0503 (6)0.0354 (5)0.0058 (4)0.0065 (4)0.0019 (4)
O5B0.1163 (12)0.0733 (9)0.0750 (9)0.0361 (9)0.0218 (8)0.0103 (7)
C1B0.0493 (8)0.0524 (9)0.0559 (9)0.0090 (7)0.0073 (7)0.0111 (7)
C2B0.0691 (11)0.0580 (10)0.0648 (11)0.0171 (9)0.0088 (8)0.0191 (8)
C3B0.0824 (13)0.0489 (9)0.0659 (11)0.0053 (9)0.0204 (10)0.0124 (8)
C4B0.0652 (11)0.0587 (10)0.0677 (11)0.0079 (8)0.0091 (9)0.0045 (9)
C5B0.0558 (9)0.0584 (10)0.0522 (9)0.0038 (8)0.0000 (7)0.0042 (7)
C6B0.0498 (8)0.0465 (8)0.0391 (7)0.0085 (6)0.0078 (6)0.0030 (6)
C7B0.0476 (8)0.0534 (9)0.0385 (7)0.0113 (7)0.0031 (6)0.0067 (6)
C8B0.0459 (8)0.0479 (8)0.0391 (7)0.0161 (6)0.0069 (6)0.0094 (6)
C9B0.0483 (8)0.0472 (8)0.0402 (7)0.0143 (6)0.0090 (6)0.0073 (6)
C10B0.0460 (8)0.0438 (8)0.0370 (7)0.0107 (6)0.0069 (6)0.0023 (6)
C11B0.0524 (8)0.0428 (8)0.0442 (8)0.0069 (6)0.0101 (6)0.0000 (6)
C12B0.0619 (10)0.0513 (9)0.0534 (9)0.0012 (8)0.0027 (8)0.0037 (7)
C13B0.0735 (11)0.0591 (10)0.0464 (9)0.0120 (9)0.0062 (8)0.0026 (8)
C14B0.0725 (11)0.0590 (10)0.0410 (8)0.0179 (8)0.0052 (7)0.0110 (7)
C15B0.0550 (9)0.0439 (8)0.0443 (8)0.0094 (7)0.0074 (7)0.0091 (6)
C16B0.0915 (15)0.0893 (15)0.0724 (13)0.0126 (12)0.0048 (11)0.0455 (11)
C17B0.0712 (11)0.0522 (9)0.0531 (9)0.0027 (8)0.0161 (8)0.0046 (7)
C18B0.0608 (9)0.0489 (9)0.0441 (9)0.0178 (7)0.0068 (7)0.0106 (7)
C19B0.199 (3)0.0553 (12)0.0878 (16)0.0041 (15)0.0135 (17)0.0348 (11)
Geometric parameters (Å, º) top
O1A—C18A1.3360 (17)O1B—C18B1.1971 (18)
O1A—C19A1.4400 (18)O2B—C18B1.327 (2)
O2A—C18A1.2019 (17)O2B—C19B1.449 (2)
O3A—C15A1.358 (2)O3B—C15B1.3620 (18)
O3A—C16A1.417 (2)O3B—C16B1.419 (2)
O4A—C10A1.3808 (17)O4B—C10B1.3785 (16)
O4A—C9A1.4488 (17)O4B—C9B1.4481 (17)
O5A—C17A1.202 (2)O5B—C17B1.1993 (19)
C1A—C6A1.382 (2)C1B—C2B1.376 (2)
C1A—C2A1.382 (2)C1B—C6B1.393 (2)
C1A—H1A0.9300C1B—H1B0.9300
C2A—C3A1.372 (3)C2B—C3B1.378 (3)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.364 (3)C3B—C4B1.371 (3)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.381 (2)C4B—C5B1.376 (2)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.392 (2)C5B—C6B1.391 (2)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.470 (2)C6B—C7B1.463 (2)
C7A—C8A1.339 (2)C7B—C8B1.334 (2)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C18A1.4844 (19)C8B—C18B1.488 (2)
C8A—C9A1.4902 (19)C8B—C9B1.5002 (19)
C9A—H9A10.9700C9B—H9B10.9700
C9A—H9A20.9700C9B—H9B20.9700
C10A—C11A1.385 (2)C10B—C11B1.389 (2)
C10A—C15A1.403 (2)C10B—C15B1.403 (2)
C11A—C12A1.403 (2)C11B—C12B1.400 (2)
C11A—C17A1.470 (2)C11B—C17B1.469 (2)
C12A—C13A1.362 (3)C12B—C13B1.359 (2)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.384 (3)C13B—C14B1.383 (2)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.382 (2)C14B—C15B1.382 (2)
C14A—H14A0.9300C14B—H14B0.9300
C16A—H16A0.9600C16B—H16D0.9600
C16A—H16B0.9600C16B—H16E0.9600
C16A—H16C0.9600C16B—H16F0.9600
C17A—H17A0.9300C17B—H17B0.9300
C19A—H19A0.9600C19B—H19D0.9600
C19A—H19B0.9600C19B—H19E0.9600
C19A—H19C0.9600C19B—H19F0.9600
C18A—O1A—C19A115.45 (12)C18B—O2B—C19B115.86 (15)
C15A—O3A—C16A118.01 (14)C15B—O3B—C16B118.03 (13)
C10A—O4A—C9A112.60 (10)C10B—O4B—C9B116.89 (10)
C6A—C1A—C2A120.38 (16)C2B—C1B—C6B120.19 (15)
C6A—C1A—H1A119.8C2B—C1B—H1B119.9
C2A—C1A—H1A119.8C6B—C1B—H1B119.9
C3A—C2A—C1A120.54 (17)C1B—C2B—C3B120.84 (17)
C3A—C2A—H2A119.7C1B—C2B—H2B119.6
C1A—C2A—H2A119.7C3B—C2B—H2B119.6
C4A—C3A—C2A119.68 (17)C4B—C3B—C2B119.44 (17)
C4A—C3A—H3A120.2C4B—C3B—H3B120.3
C2A—C3A—H3A120.2C2B—C3B—H3B120.3
C3A—C4A—C5A120.48 (17)C3B—C4B—C5B120.37 (17)
C3A—C4A—H4A119.8C3B—C4B—H4B119.8
C5A—C4A—H4A119.8C5B—C4B—H4B119.8
C4A—C5A—C6A120.41 (17)C4B—C5B—C6B120.89 (16)
C4A—C5A—H5A119.8C4B—C5B—H5B119.6
C6A—C5A—H5A119.8C6B—C5B—H5B119.6
C1A—C6A—C5A118.48 (14)C5B—C6B—C1B118.27 (14)
C1A—C6A—C7A122.41 (14)C5B—C6B—C7B119.47 (14)
C5A—C6A—C7A119.08 (14)C1B—C6B—C7B122.19 (13)
C8A—C7A—C6A128.24 (14)C8B—C7B—C6B128.96 (13)
C8A—C7A—H7A115.9C8B—C7B—H7B115.5
C6A—C7A—H7A115.9C6B—C7B—H7B115.5
C7A—C8A—C18A120.49 (13)C7B—C8B—C18B116.47 (13)
C7A—C8A—C9A124.49 (13)C7B—C8B—C9B123.79 (13)
C18A—C8A—C9A114.79 (12)C18B—C8B—C9B119.68 (13)
O4A—C9A—C8A110.18 (11)O4B—C9B—C8B108.60 (11)
O4A—C9A—H9A1109.6O4B—C9B—H9B1110.0
C8A—C9A—H9A1109.6C8B—C9B—H9B1110.0
O4A—C9A—H9A2109.6O4B—C9B—H9B2110.0
C8A—C9A—H9A2109.6C8B—C9B—H9B2110.0
H9A1—C9A—H9A2108.1H9B1—C9B—H9B2108.4
O4A—C10A—C11A119.70 (13)O4B—C10B—C11B118.40 (12)
O4A—C10A—C15A120.06 (13)O4B—C10B—C15B121.71 (13)
C11A—C10A—C15A120.19 (14)C11B—C10B—C15B119.66 (13)
C10A—C11A—C12A119.64 (16)C10B—C11B—C12B119.55 (14)
C10A—C11A—C17A120.45 (14)C10B—C11B—C17B120.62 (13)
C12A—C11A—C17A119.90 (15)C12B—C11B—C17B119.82 (14)
C13A—C12A—C11A119.87 (17)C13B—C12B—C11B120.21 (15)
C13A—C12A—H12A120.1C13B—C12B—H12B119.9
C11A—C12A—H12A120.1C11B—C12B—H12B119.9
C12A—C13A—C14A120.74 (17)C12B—C13B—C14B120.83 (15)
C12A—C13A—H13A119.6C12B—C13B—H13B119.6
C14A—C13A—H13A119.6C14B—C13B—H13B119.6
C15A—C14A—C13A120.63 (17)C15B—C14B—C13B120.14 (15)
C15A—C14A—H14A119.7C15B—C14B—H14B119.9
C13A—C14A—H14A119.7C13B—C14B—H14B119.9
O3A—C15A—C14A125.62 (15)O3B—C15B—C14B124.42 (14)
O3A—C15A—C10A115.46 (13)O3B—C15B—C10B116.01 (13)
C14A—C15A—C10A118.91 (16)C14B—C15B—C10B119.55 (14)
O3A—C16A—H16A109.5O3B—C16B—H16D109.5
O3A—C16A—H16B109.5O3B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
O3A—C16A—H16C109.5O3B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
O5A—C17A—C11A124.33 (17)O5B—C17B—C11B124.08 (16)
O5A—C17A—H17A117.8O5B—C17B—H17B118.0
C11A—C17A—H17A117.8C11B—C17B—H17B118.0
O2A—C18A—O1A122.83 (13)O1B—C18B—O2B123.09 (15)
O2A—C18A—C8A123.97 (13)O1B—C18B—C8B125.27 (15)
O1A—C18A—C8A113.20 (12)O2B—C18B—C8B111.64 (13)
O1A—C19A—H19A109.5O2B—C19B—H19D109.5
O1A—C19A—H19B109.5O2B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
O1A—C19A—H19C109.5O2B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C6A—C1A—C2A—C3A0.5 (3)C6B—C1B—C2B—C3B0.9 (3)
C1A—C2A—C3A—C4A0.4 (3)C1B—C2B—C3B—C4B0.1 (3)
C2A—C3A—C4A—C5A0.5 (3)C2B—C3B—C4B—C5B0.8 (3)
C3A—C4A—C5A—C6A1.4 (3)C3B—C4B—C5B—C6B1.0 (3)
C2A—C1A—C6A—C5A0.4 (3)C4B—C5B—C6B—C1B0.3 (2)
C2A—C1A—C6A—C7A178.36 (16)C4B—C5B—C6B—C7B177.33 (15)
C4A—C5A—C6A—C1A1.3 (3)C2B—C1B—C6B—C5B0.7 (2)
C4A—C5A—C6A—C7A179.34 (16)C2B—C1B—C6B—C7B176.33 (15)
C1A—C6A—C7A—C8A40.2 (2)C5B—C6B—C7B—C8B141.00 (17)
C5A—C6A—C7A—C8A141.79 (17)C1B—C6B—C7B—C8B42.0 (2)
C6A—C7A—C8A—C18A178.94 (14)C6B—C7B—C8B—C18B175.41 (14)
C6A—C7A—C8A—C9A6.8 (2)C6B—C7B—C8B—C9B7.3 (2)
C10A—O4A—C9A—C8A168.47 (11)C10B—O4B—C9B—C8B174.31 (11)
C7A—C8A—C9A—O4A104.79 (16)C7B—C8B—C9B—O4B105.02 (16)
C18A—C8A—C9A—O4A80.66 (14)C18B—C8B—C9B—O4B77.76 (16)
C9A—O4A—C10A—C11A106.93 (14)C9B—O4B—C10B—C11B119.51 (14)
C9A—O4A—C10A—C15A75.55 (16)C9B—O4B—C10B—C15B66.03 (18)
O4A—C10A—C11A—C12A176.58 (13)O4B—C10B—C11B—C12B172.24 (14)
C15A—C10A—C11A—C12A0.9 (2)C15B—C10B—C11B—C12B2.3 (2)
O4A—C10A—C11A—C17A4.4 (2)O4B—C10B—C11B—C17B9.1 (2)
C15A—C10A—C11A—C17A178.09 (14)C15B—C10B—C11B—C17B176.36 (14)
C10A—C11A—C12A—C13A0.7 (3)C10B—C11B—C12B—C13B2.4 (2)
C17A—C11A—C12A—C13A178.30 (17)C17B—C11B—C12B—C13B176.30 (16)
C11A—C12A—C13A—C14A0.1 (3)C11B—C12B—C13B—C14B0.5 (3)
C12A—C13A—C14A—C15A0.8 (3)C12B—C13B—C14B—C15B1.6 (3)
C16A—O3A—C15A—C14A10.6 (2)C16B—O3B—C15B—C14B0.2 (3)
C16A—O3A—C15A—C10A170.80 (15)C16B—O3B—C15B—C10B179.14 (17)
C13A—C14A—C15A—O3A177.99 (16)C13B—C14B—C15B—O3B177.30 (16)
C13A—C14A—C15A—C10A0.6 (2)C13B—C14B—C15B—C10B1.6 (2)
O4A—C10A—C15A—O3A1.5 (2)O4B—C10B—C15B—O3B4.9 (2)
C11A—C10A—C15A—O3A179.01 (13)C11B—C10B—C15B—O3B179.35 (13)
O4A—C10A—C15A—C14A177.22 (14)O4B—C10B—C15B—C14B174.06 (14)
C11A—C10A—C15A—C14A0.3 (2)C11B—C10B—C15B—C14B0.3 (2)
C10A—C11A—C17A—O5A170.69 (17)C10B—C11B—C17B—O5B178.61 (18)
C12A—C11A—C17A—O5A10.3 (3)C12B—C11B—C17B—O5B2.7 (3)
C19A—O1A—C18A—O2A2.1 (2)C19B—O2B—C18B—O1B0.6 (3)
C19A—O1A—C18A—C8A177.28 (14)C19B—O2B—C18B—C8B178.78 (19)
C7A—C8A—C18A—O2A177.55 (15)C7B—C8B—C18B—O1B5.9 (2)
C9A—C8A—C18A—O2A2.8 (2)C9B—C8B—C18B—O1B176.72 (15)
C7A—C8A—C18A—O1A1.85 (19)C7B—C8B—C18B—O2B174.76 (15)
C9A—C8A—C18A—O1A176.63 (12)C9B—C8B—C18B—O2B2.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17A—H17A···O2A0.932.483.354 (2)156
C17A—H17A···O4A0.932.502.8164 (19)100
C17B—H17B···O4B0.932.472.8004 (19)101
C9A—H9A2···O3A0.972.493.0167 (18)114
C9B—H9B1···O3B0.972.362.9416 (17)118
C7B—H7B···O1B0.932.412.7847 (18)104
C7A—H7A···O1A0.932.292.6914 (17)106
C9A—H9A1···O4Bi0.972.553.2215 (16)126
C19B—H19D···O5Aii0.962.433.275 (3)147
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC19H18O5
Mr326.33
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.4696 (5), 12.1662 (7), 16.9860 (9)
α, β, γ (°)94.423 (3), 100.038 (3), 103.475 (3)
V3)1663.33 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEXII area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
30114, 8303, 5258
Rint0.032
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.137, 0.93
No. of reflections8303
No. of parameters433
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.18

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17A—H17A···O2A0.932.483.354 (2)155.7
C17A—H17A···O4A0.932.502.8164 (19)100.3
C17B—H17B···O4B0.932.472.8004 (19)100.8
C9A—H9A2···O3A0.972.493.0167 (18)114.1
C9B—H9B1···O3B0.972.362.9416 (17)117.9
C7B—H7B···O1B0.932.412.7847 (18)104.2
C7A—H7A···O1A0.932.292.6914 (17)105.7
C9A—H9A1···O4Bi0.972.553.2215 (16)126.4
C19B—H19D···O5Aii0.962.433.275 (3)146.6
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+1, y+1, z+2.
 

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics University of Madras, India, for the data collection.

References

First citationBakthadoss, M., Sivakumar, G. & Kannan, D. (2009). Org. Lett. 11, 4466–4469.  Web of Science CSD CrossRef PubMed CAS
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationJones, P. G. & Jäger, S. (2003). Acta Cryst. E59, o369–o371.  Web of Science CSD CrossRef IUCr Journals
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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 citationWang, X.-B. & Kong, L.-Y. (2006). Acta Cryst. E62, o4558–o4559.  Web of Science CSD CrossRef IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals
First citationZhu, J., Zhu, H., Kobamoto, N., Yasuda, M. & Tawata, S. (2000). J. Pestic. Sci. 25, 263–266.  CrossRef CAS

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