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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 67| Part 12| December 2011| Page o3245
https://doi.org/10.1107/S1600536811046587

(Z)-Methyl 2-[(2-eth­­oxy-6-formyl­phen­­oxy)meth­yl]-3-(4-ethyl­phen­yl)acrylate

Rajeswari Gangadharan,a K. Sethusankar,b* Raman Selvakumarc and Manickam Bakthadossc

aDepartment of Physics, Ethiraj College for Women (Autonomous), Chennai 600 008, India, bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 22 October 2011; accepted 4 November 2011; online 9 November 2011)

The title compound, C22H24O5, consists of two substituted benzene rings linked by an ethyl acrylate group. The dihedral angle between the two benzene rings is 58.39 (7)°. The crystal packing is governed by two C—H⋯O inter­actions, one of which forms centrosymmetric dimers with a graph-set descriptor of R22(18).

Related literature

For applications of acrylate derivatives, see: Xiao et al. (2008[Xiao, Z.-P., Fang, R.-Q., Li, H.-Q., Xue, J.-Y., Zheng, Y. & Zhu, H.-L. (2008). Eur. J. Med. Chem. 43, 1828-1836.]). For a related structure, see: Gong et al. (2008[Gong, H.-B., Wang, J., Liu, Y. & Wang, L. (2008). Acta Cryst. E64, o2373.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C22H24O5

  • Mr = 368.41

  • Triclinic, [P \overline 1]

  • a = 9.6746 (3) Å

  • b = 9.9435 (3) Å

  • c = 10.7935 (3) Å

  • α = 77.595 (1)°

  • β = 85.433 (2)°

  • γ = 76.752 (1)°

  • V = 986.59 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm
Data collection

  • Bruker SMART APEXII area-detector diffractometer

  • 25506 measured reflections

  • 6646 independent reflections

  • 4400 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.164

  • S = 1.02

  • 6646 reflections

  • 247 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C7—H7⋯O5i 0.93 2.58 3.368 (2) 143
C17—H17⋯O1ii 0.93 2.56 3.454 (2) 161
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z-1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811046587/pv2468sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046587/pv2468Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046587/pv2468Isup3.cml

checkCIF report


Comment top

Phenyl acrylates show considerable antibacterial activities against Staphylococcus aureus (Xiao et al., 2008).

In the title compound (Fig. 1), the methyl acrylate group is planar and forms dihedral angles 33.43 (4)° and 41.71 (4)° with the two phenyl rings (C1–C6) and (C15–C20), respectively. The inter planar angle between the two phenyl rings is 58.39 (7)°. The title compound exhibits structural similarities with the already reported related structure (Gong et al., 2008).

The crystal packing is governed by two C—H···O interactions, one of which forms centrosymmetric dimers with graph set descriptor of R22(18) (Bernstein et al.1995) (Fig. 2 and Table 1)

Related literature top

For applications of acrylate derivatives, see: Xiao et al. (2008). For a related structure, see: Gong et al. (2008). For graph-set notation, see: Bernstein et al. (1995)

Experimental top

A solution of 3-ethoxysalicylaldehyde (3.54 mmol, 0.58 g) and potassium carbonate (3.89 mmol, 0.53 g) in acetonitrile (10 ml) was stirred for 15 minutes at room temperature. To this solution, (Z)-methyl 2-(bromomethyl)-3-(4-ethylphenyl)acrylate (3.54 mmol, 1 g) was added dropwise. After the completion of the reaction as indicated by TLC, acetonitrile was evaporated. Ethylacetate (15 ml) and water (15 ml) were added to the crude mass and extracted. 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 colorless solid (1.05 g, 81%). Recrystallization was carried out using ethylacetate as solvent.

Refinement top

The hydrogen atoms were placed in calculated positions with C—H = 0.93 to 0.97 Å and refined in the riding model with isotropic displacement parameters: Uiso(H) = 1.5Ueq(C)for methyl group and Uiso(H) = 1.2Ueq(C)for other groups.

Structure description top

Phenyl acrylates show considerable antibacterial activities against Staphylococcus aureus (Xiao et al., 2008).

In the title compound (Fig. 1), the methyl acrylate group is planar and forms dihedral angles 33.43 (4)° and 41.71 (4)° with the two phenyl rings (C1–C6) and (C15–C20), respectively. The inter planar angle between the two phenyl rings is 58.39 (7)°. The title compound exhibits structural similarities with the already reported related structure (Gong et al., 2008).

The crystal packing is governed by two C—H···O interactions, one of which forms centrosymmetric dimers with graph set descriptor of R22(18) (Bernstein et al.1995) (Fig. 2 and Table 1)

For applications of acrylate derivatives, see: Xiao et al. (2008). For a related structure, see: Gong et al. (2008). For graph-set notation, see: Bernstein et al. (1995)

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. The molecular structure of the title compound with the atom numbering scheme, displacement ellipsoids are drawn at 30% probability level. H atoms are drawn as small spheres of arbitary radii.
[Figure 2] Fig. 2. Part of crystal structure of the title compound, showing the formation of R22(18) dimers viewed along the a-axis. Dashed lines indicates C—H···O intermolecular interactions.
(Z)-Methyl 2-[(2-ethoxy-6-formylphenoxy)methyl]-3-(4-ethylphenyl)acrylate top
Crystal data top
C22H24O5Z = 2
Mr = 368.41F(000) = 392
Triclinic, P1Dx = 1.240 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6746 (3) ÅCell parameters from 6646 reflections
b = 9.9435 (3) Åθ = 1.9–31.7°
c = 10.7935 (3) ŵ = 0.09 mm−1
α = 77.595 (1)°T = 293 K
β = 85.433 (2)°Block, colorless
γ = 76.752 (1)°0.30 × 0.25 × 0.20 mm
V = 986.59 (5) Å3
Data collection top
Bruker SMART APEXII area-detector
diffractometer		4400 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 31.7°, θmin = 1.9°
ω and φ scansh = −13→14
25506 measured reflectionsk = −14→14
6646 independent reflectionsl = −15→15
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.083P)2 + 0.1225P]
where P = (Fo2 + 2Fc2)/3
6646 reflections(Δ/σ)max < 0.001
247 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C22H24O5γ = 76.752 (1)°
Mr = 368.41V = 986.59 (5) Å3
Triclinic, P1Z = 2
a = 9.6746 (3) ÅMo Kα radiation
b = 9.9435 (3) ŵ = 0.09 mm−1
c = 10.7935 (3) ÅT = 293 K
α = 77.595 (1)°0.30 × 0.25 × 0.20 mm
β = 85.433 (2)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer		4400 reflections with I > 2σ(I)
25506 measured reflectionsRint = 0.025
6646 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 1.02Δρmax = 0.25 e Å−3
6646 reflectionsΔρmin = −0.21 e Å−3
247 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
C10.31037 (15)0.58360 (15)1.00970 (12)0.0513 (3)
H10.32750.49341.06020.062*
C20.27416 (17)0.69925 (18)1.06433 (12)0.0587 (4)
H20.26980.68711.15230.070*
C30.24384 (16)0.83397 (16)0.99082 (13)0.0544 (3)
H30.21800.91131.02980.065*
C40.25171 (13)0.85470 (13)0.85931 (12)0.0429 (3)
C50.29508 (12)0.73676 (12)0.80276 (10)0.0370 (2)
C60.32154 (13)0.60162 (13)0.87760 (11)0.0407 (2)
C70.35960 (15)0.47780 (13)0.81699 (13)0.0476 (3)
H70.38120.49370.73030.057*
C80.14625 (18)1.10162 (16)0.82610 (18)0.0674 (4)
H8A0.20851.12870.87790.081*
H8B0.06451.08030.87810.081*
C90.1000 (2)1.21793 (18)0.7157 (2)0.0875 (6)
H9A0.18191.23990.66640.131*
H9B0.04771.29990.74550.131*
H9C0.04051.18900.66400.131*
C100.41026 (15)0.83034 (13)0.61113 (12)0.0460 (3)
H10A0.47420.83630.67350.055*
H10B0.36430.92540.57110.055*
C110.49176 (13)0.75448 (12)0.51363 (11)0.0411 (3)
C120.60371 (14)0.63091 (13)0.56688 (11)0.0448 (3)
C130.79009 (18)0.44609 (17)0.52593 (16)0.0675 (4)
H13A0.86160.47990.55950.101*
H13B0.83080.40060.45750.101*
H13C0.75420.37990.59150.101*
C140.47471 (13)0.79509 (12)0.38798 (11)0.0411 (3)
H140.53620.74120.33760.049*
C150.37025 (13)0.91476 (12)0.32064 (11)0.0403 (3)
C160.41376 (13)0.99223 (13)0.20705 (10)0.0415 (3)
H160.50490.96350.17390.050*
C170.32363 (13)1.11147 (13)0.14246 (11)0.0436 (3)
H170.35671.16380.06870.052*
C180.18579 (14)1.15383 (13)0.18558 (12)0.0438 (3)
C190.13937 (15)1.07222 (15)0.29530 (15)0.0588 (4)
H190.04551.09620.32390.071*
C200.23041 (15)0.95586 (15)0.36287 (14)0.0562 (4)
H200.19760.90460.43740.067*
C210.08788 (16)1.28446 (14)0.11572 (14)0.0529 (3)
H21A0.13711.32390.03960.064*
H21B0.00581.25800.08980.064*
C220.03783 (18)1.39611 (16)0.19423 (17)0.0664 (4)
H22A−0.01491.35930.26780.100*
H22B−0.02191.47710.14450.100*
H22C0.11851.42290.22030.100*
O10.36468 (14)0.35836 (11)0.87125 (11)0.0706 (3)
O20.21967 (11)0.98154 (9)0.77707 (9)0.0546 (3)
O30.30428 (9)0.75349 (9)0.67258 (7)0.0420 (2)
O40.62780 (13)0.59403 (13)0.67774 (9)0.0718 (3)
O50.67596 (12)0.56277 (10)0.47986 (9)0.0596 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0547 (8)0.0589 (8)0.0368 (6)−0.0115 (6)−0.0013 (5)−0.0034 (5)
C20.0677 (9)0.0775 (10)0.0329 (6)−0.0189 (7)0.0017 (6)−0.0135 (6)
C30.0581 (8)0.0663 (8)0.0470 (7)−0.0161 (6)0.0069 (6)−0.0294 (6)
C40.0428 (6)0.0439 (6)0.0434 (6)−0.0083 (5)0.0031 (5)−0.0150 (5)
C50.0374 (6)0.0427 (6)0.0313 (5)−0.0076 (4)0.0004 (4)−0.0103 (4)
C60.0399 (6)0.0442 (6)0.0367 (5)−0.0080 (4)0.0002 (4)−0.0072 (4)
C70.0534 (7)0.0417 (6)0.0442 (6)−0.0067 (5)0.0025 (5)−0.0065 (5)
C80.0644 (10)0.0504 (8)0.0862 (11)0.0030 (7)0.0051 (8)−0.0307 (8)
C90.0839 (13)0.0477 (9)0.1221 (17)0.0050 (8)−0.0087 (12)−0.0170 (9)
C100.0620 (8)0.0391 (6)0.0384 (6)−0.0151 (5)0.0069 (5)−0.0099 (4)
C110.0490 (7)0.0375 (5)0.0353 (5)−0.0085 (5)0.0015 (5)−0.0061 (4)
C120.0506 (7)0.0459 (6)0.0354 (6)−0.0084 (5)−0.0033 (5)−0.0043 (5)
C130.0659 (10)0.0592 (9)0.0648 (9)0.0140 (7)−0.0140 (7)−0.0106 (7)
C140.0472 (6)0.0359 (5)0.0366 (5)−0.0041 (4)0.0007 (5)−0.0059 (4)
C150.0462 (6)0.0352 (5)0.0372 (5)−0.0057 (4)−0.0009 (5)−0.0061 (4)
C160.0410 (6)0.0471 (6)0.0335 (5)−0.0054 (5)−0.0007 (4)−0.0065 (4)
C170.0480 (7)0.0451 (6)0.0351 (5)−0.0096 (5)−0.0041 (5)−0.0021 (4)
C180.0460 (7)0.0378 (6)0.0463 (6)−0.0065 (5)−0.0064 (5)−0.0064 (5)
C190.0440 (7)0.0520 (7)0.0676 (9)−0.0015 (5)0.0100 (6)0.0019 (6)
C200.0522 (8)0.0474 (7)0.0569 (8)−0.0064 (6)0.0117 (6)0.0063 (6)
C210.0512 (7)0.0462 (7)0.0557 (8)−0.0027 (5)−0.0115 (6)−0.0029 (6)
C220.0629 (9)0.0505 (8)0.0788 (10)0.0062 (7)−0.0115 (8)−0.0145 (7)
O10.0969 (9)0.0419 (5)0.0657 (7)−0.0109 (5)0.0071 (6)−0.0030 (5)
O20.0641 (6)0.0391 (5)0.0563 (5)−0.0010 (4)0.0073 (5)−0.0149 (4)
O30.0526 (5)0.0433 (4)0.0317 (4)−0.0127 (3)0.0005 (3)−0.0090 (3)
O40.0754 (8)0.0890 (8)0.0372 (5)0.0058 (6)−0.0124 (5)−0.0039 (5)
O50.0704 (7)0.0530 (5)0.0423 (5)0.0145 (5)−0.0087 (4)−0.0085 (4)
Geometric parameters (Å, º) top
C1—C21.366 (2)C11—C121.4829 (17)
C1—C61.3969 (17)C12—O41.1990 (15)
C1—H10.9300C12—O51.3347 (16)
C2—C31.382 (2)C13—O51.4370 (16)
C2—H20.9300C13—H13A0.9600
C3—C41.3882 (18)C13—H13B0.9600
C3—H30.9300C13—H13C0.9600
C4—O21.3632 (15)C14—C151.4696 (15)
C4—C51.4019 (16)C14—H140.9300
C5—O31.3771 (13)C15—C201.3905 (18)
C5—C61.3901 (16)C15—C161.3908 (16)
C6—C71.4763 (17)C16—C171.3856 (16)
C7—O11.1978 (16)C16—H160.9300
C7—H70.9300C17—C181.3785 (18)
C8—O21.4259 (16)C17—H170.9300
C8—C91.488 (3)C18—C191.3901 (19)
C8—H8A0.9700C18—C211.5106 (17)
C8—H8B0.9700C19—C201.3853 (19)
C9—H9A0.9600C19—H190.9300
C9—H9B0.9600C20—H200.9300
C9—H9C0.9600C21—C221.509 (2)
C10—O31.4520 (15)C21—H21A0.9700
C10—C111.4949 (16)C21—H21B0.9700
C10—H10A0.9700C22—H22A0.9600
C10—H10B0.9700C22—H22B0.9600
C11—C141.3414 (16)C22—H22C0.9600
C2—C1—C6119.61 (12)O5—C12—C11113.84 (10)
C2—C1—H1120.2O5—C13—H13A109.5
C6—C1—H1120.2O5—C13—H13B109.5
C1—C2—C3121.00 (12)H13A—C13—H13B109.5
C1—C2—H2119.5O5—C13—H13C109.5
C3—C2—H2119.5H13A—C13—H13C109.5
C2—C3—C4120.52 (12)H13B—C13—H13C109.5
C2—C3—H3119.7C11—C14—C15127.62 (11)
C4—C3—H3119.7C11—C14—H14116.2
O2—C4—C3125.90 (11)C15—C14—H14116.2
O2—C4—C5115.38 (10)C20—C15—C16117.66 (11)
C3—C4—C5118.72 (12)C20—C15—C14124.35 (11)
O3—C5—C6119.47 (10)C16—C15—C14117.99 (11)
O3—C5—C4120.26 (10)C17—C16—C15121.10 (11)
C6—C5—C4120.17 (10)C17—C16—H16119.4
C5—C6—C1119.87 (11)C15—C16—H16119.4
C5—C6—C7119.81 (10)C18—C17—C16121.16 (11)
C1—C6—C7120.32 (11)C18—C17—H17119.4
O1—C7—C6124.82 (12)C16—C17—H17119.4
O1—C7—H7117.6C17—C18—C19117.90 (11)
C6—C7—H7117.6C17—C18—C21121.17 (11)
O2—C8—C9107.34 (15)C19—C18—C21120.94 (12)
O2—C8—H8A110.2C20—C19—C18121.21 (13)
C9—C8—H8A110.2C20—C19—H19119.4
O2—C8—H8B110.2C18—C19—H19119.4
C9—C8—H8B110.2C19—C20—C15120.81 (12)
H8A—C8—H8B108.5C19—C20—H20119.6
C8—C9—H9A109.5C15—C20—H20119.6
C8—C9—H9B109.5C22—C21—C18113.21 (12)
H9A—C9—H9B109.5C22—C21—H21A108.9
C8—C9—H9C109.5C18—C21—H21A108.9
H9A—C9—H9C109.5C22—C21—H21B108.9
H9B—C9—H9C109.5C18—C21—H21B108.9
O3—C10—C11108.76 (10)H21A—C21—H21B107.7
O3—C10—H10A109.9C21—C22—H22A109.5
C11—C10—H10A109.9C21—C22—H22B109.5
O3—C10—H10B109.9H22A—C22—H22B109.5
C11—C10—H10B109.9C21—C22—H22C109.5
H10A—C10—H10B108.3H22A—C22—H22C109.5
C14—C11—C12120.99 (11)H22B—C22—H22C109.5
C14—C11—C10125.04 (11)C4—O2—C8118.22 (11)
C12—C11—C10113.86 (10)C5—O3—C10114.56 (9)
O4—C12—O5122.44 (12)C12—O5—C13115.99 (11)
O4—C12—C11123.71 (12)
C6—C1—C2—C32.1 (2)C10—C11—C14—C15−3.6 (2)
C1—C2—C3—C4−1.0 (2)C11—C14—C15—C20−38.7 (2)
C2—C3—C4—O2177.56 (13)C11—C14—C15—C16141.38 (14)
C2—C3—C4—C5−1.9 (2)C20—C15—C16—C174.00 (19)
O2—C4—C5—O30.58 (17)C14—C15—C16—C17−176.03 (11)
C3—C4—C5—O3−179.90 (11)C15—C16—C17—C18−2.89 (19)
O2—C4—C5—C6−175.87 (11)C16—C17—C18—C19−0.7 (2)
C3—C4—C5—C63.65 (18)C16—C17—C18—C21179.52 (12)
O3—C5—C6—C1−179.04 (11)C17—C18—C19—C203.1 (2)
C4—C5—C6—C1−2.56 (18)C21—C18—C19—C20−177.14 (14)
O3—C5—C6—C70.21 (18)C18—C19—C20—C15−1.9 (3)
C4—C5—C6—C7176.69 (11)C16—C15—C20—C19−1.6 (2)
C2—C1—C6—C5−0.3 (2)C14—C15—C20—C19178.41 (14)
C2—C1—C6—C7−179.58 (13)C17—C18—C21—C22−118.36 (15)
C5—C6—C7—O1−168.90 (14)C19—C18—C21—C2261.87 (19)
C1—C6—C7—O110.3 (2)C3—C4—O2—C8−12.8 (2)
O3—C10—C11—C14103.91 (14)C5—C4—O2—C8166.63 (12)
O3—C10—C11—C12−79.81 (13)C9—C8—O2—C4−169.18 (14)
C14—C11—C12—O4176.44 (14)C6—C5—O3—C10−119.28 (12)
C10—C11—C12—O40.0 (2)C4—C5—O3—C1064.25 (14)
C14—C11—C12—O5−3.89 (18)C11—C10—O3—C5135.17 (10)
C10—C11—C12—O5179.67 (11)O4—C12—O5—C13−3.1 (2)
C12—C11—C14—C15−179.59 (12)C11—C12—O5—C13177.20 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O5i0.932.583.368 (2)143
C17—H17···O1ii0.932.563.454 (2)161
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z−1.

Experimental details

Crystal data
Chemical formulaC22H24O5
Mr368.41
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.6746 (3), 9.9435 (3), 10.7935 (3)
α, β, γ (°)77.595 (1), 85.433 (2), 76.752 (1)
V (Å3)986.59 (5)
Z2
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART APEXII area-detector
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		25506, 6646, 4400
Rint0.025
(sin θ/λ)max (Å−1)0.740
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.164, 1.02
No. of reflections6646
No. of parameters247
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.25, −0.21

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
D—H···AD—HH···AD···AD—H···A
C7—H7···O5i0.932.583.368 (2)143
C17—H17···O1ii0.932.563.454 (2)161
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z−1.
 

Acknowledgements

RG and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Department of Physics, for providing facilities in the department to carry out this work.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGong, H.-B., Wang, J., Liu, Y. & Wang, L. (2008). Acta Cryst. E64, o2373.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXiao, Z.-P., Fang, R.-Q., Li, H.-Q., Xue, J.-Y., Zheng, Y. & Zhu, H.-L. (2008). Eur. J. Med. Chem. 43, 1828–1836.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3245
https://doi.org/10.1107/S1600536811046587
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