organic compounds
(Z)-Methyl 2-[(2-ethoxy-6-formylphenoxy)methyl]-3-(4-ethylphenyl)acrylate
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
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). For a related structure, see: Gong et al. (2008). For graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; 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 and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536811046587/pv2468sup1.cif
contains datablocks global, I. DOI: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
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.
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.
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)
Data collection: APEX2 (Bruker, 2008); cell
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).C22H24O5 | Z = 2 |
Mr = 368.41 | F(000) = 392 |
Triclinic, P1 | Dx = 1.240 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6746 (3) Å | Cell parameters from 6646 reflections |
b = 9.9435 (3) Å | θ = 1.9–31.7° |
c = 10.7935 (3) Å | µ = 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 |
Bruker SMART APEXII area-detector diffractometer | 4400 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 31.7°, θmin = 1.9° |
ω and φ scans | h = −13→14 |
25506 measured reflections | k = −14→14 |
6646 independent reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-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 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C22H24O5 | γ = 76.752 (1)° |
Mr = 368.41 | V = 986.59 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6746 (3) Å | Mo Kα radiation |
b = 9.9435 (3) Å | µ = 0.09 mm−1 |
c = 10.7935 (3) Å | T = 293 K |
α = 77.595 (1)° | 0.30 × 0.25 × 0.20 mm |
β = 85.433 (2)° |
Bruker SMART APEXII area-detector diffractometer | 4400 reflections with I > 2σ(I) |
25506 measured reflections | Rint = 0.025 |
6646 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.25 e Å−3 |
6646 reflections | Δρmin = −0.21 e Å−3 |
247 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.31037 (15) | 0.58360 (15) | 1.00970 (12) | 0.0513 (3) | |
H1 | 0.3275 | 0.4934 | 1.0602 | 0.062* | |
C2 | 0.27416 (17) | 0.69925 (18) | 1.06433 (12) | 0.0587 (4) | |
H2 | 0.2698 | 0.6871 | 1.1523 | 0.070* | |
C3 | 0.24384 (16) | 0.83397 (16) | 0.99082 (13) | 0.0544 (3) | |
H3 | 0.2180 | 0.9113 | 1.0298 | 0.065* | |
C4 | 0.25171 (13) | 0.85470 (13) | 0.85931 (12) | 0.0429 (3) | |
C5 | 0.29508 (12) | 0.73676 (12) | 0.80276 (10) | 0.0370 (2) | |
C6 | 0.32154 (13) | 0.60162 (13) | 0.87760 (11) | 0.0407 (2) | |
C7 | 0.35960 (15) | 0.47780 (13) | 0.81699 (13) | 0.0476 (3) | |
H7 | 0.3812 | 0.4937 | 0.7303 | 0.057* | |
C8 | 0.14625 (18) | 1.10162 (16) | 0.82610 (18) | 0.0674 (4) | |
H8A | 0.2085 | 1.1287 | 0.8779 | 0.081* | |
H8B | 0.0645 | 1.0803 | 0.8781 | 0.081* | |
C9 | 0.1000 (2) | 1.21793 (18) | 0.7157 (2) | 0.0875 (6) | |
H9A | 0.1819 | 1.2399 | 0.6664 | 0.131* | |
H9B | 0.0477 | 1.2999 | 0.7455 | 0.131* | |
H9C | 0.0405 | 1.1890 | 0.6640 | 0.131* | |
C10 | 0.41026 (15) | 0.83034 (13) | 0.61113 (12) | 0.0460 (3) | |
H10A | 0.4742 | 0.8363 | 0.6735 | 0.055* | |
H10B | 0.3643 | 0.9254 | 0.5711 | 0.055* | |
C11 | 0.49176 (13) | 0.75448 (12) | 0.51363 (11) | 0.0411 (3) | |
C12 | 0.60371 (14) | 0.63091 (13) | 0.56688 (11) | 0.0448 (3) | |
C13 | 0.79009 (18) | 0.44609 (17) | 0.52593 (16) | 0.0675 (4) | |
H13A | 0.8616 | 0.4799 | 0.5595 | 0.101* | |
H13B | 0.8308 | 0.4006 | 0.4575 | 0.101* | |
H13C | 0.7542 | 0.3799 | 0.5915 | 0.101* | |
C14 | 0.47471 (13) | 0.79509 (12) | 0.38798 (11) | 0.0411 (3) | |
H14 | 0.5362 | 0.7412 | 0.3376 | 0.049* | |
C15 | 0.37025 (13) | 0.91476 (12) | 0.32064 (11) | 0.0403 (3) | |
C16 | 0.41376 (13) | 0.99223 (13) | 0.20705 (10) | 0.0415 (3) | |
H16 | 0.5049 | 0.9635 | 0.1739 | 0.050* | |
C17 | 0.32363 (13) | 1.11147 (13) | 0.14246 (11) | 0.0436 (3) | |
H17 | 0.3567 | 1.1638 | 0.0687 | 0.052* | |
C18 | 0.18579 (14) | 1.15383 (13) | 0.18558 (12) | 0.0438 (3) | |
C19 | 0.13937 (15) | 1.07222 (15) | 0.29530 (15) | 0.0588 (4) | |
H19 | 0.0455 | 1.0962 | 0.3239 | 0.071* | |
C20 | 0.23041 (15) | 0.95586 (15) | 0.36287 (14) | 0.0562 (4) | |
H20 | 0.1976 | 0.9046 | 0.4374 | 0.067* | |
C21 | 0.08788 (16) | 1.28446 (14) | 0.11572 (14) | 0.0529 (3) | |
H21A | 0.1371 | 1.3239 | 0.0396 | 0.064* | |
H21B | 0.0058 | 1.2580 | 0.0898 | 0.064* | |
C22 | 0.03783 (18) | 1.39611 (16) | 0.19423 (17) | 0.0664 (4) | |
H22A | −0.0149 | 1.3593 | 0.2678 | 0.100* | |
H22B | −0.0219 | 1.4771 | 0.1445 | 0.100* | |
H22C | 0.1185 | 1.4229 | 0.2203 | 0.100* | |
O1 | 0.36468 (14) | 0.35836 (11) | 0.87125 (11) | 0.0706 (3) | |
O2 | 0.21967 (11) | 0.98154 (9) | 0.77707 (9) | 0.0546 (3) | |
O3 | 0.30428 (9) | 0.75349 (9) | 0.67258 (7) | 0.0420 (2) | |
O4 | 0.62780 (13) | 0.59403 (13) | 0.67774 (9) | 0.0718 (3) | |
O5 | 0.67596 (12) | 0.56277 (10) | 0.47986 (9) | 0.0596 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0547 (8) | 0.0589 (8) | 0.0368 (6) | −0.0115 (6) | −0.0013 (5) | −0.0034 (5) |
C2 | 0.0677 (9) | 0.0775 (10) | 0.0329 (6) | −0.0189 (7) | 0.0017 (6) | −0.0135 (6) |
C3 | 0.0581 (8) | 0.0663 (8) | 0.0470 (7) | −0.0161 (6) | 0.0069 (6) | −0.0294 (6) |
C4 | 0.0428 (6) | 0.0439 (6) | 0.0434 (6) | −0.0083 (5) | 0.0031 (5) | −0.0150 (5) |
C5 | 0.0374 (6) | 0.0427 (6) | 0.0313 (5) | −0.0076 (4) | 0.0004 (4) | −0.0103 (4) |
C6 | 0.0399 (6) | 0.0442 (6) | 0.0367 (5) | −0.0080 (4) | 0.0002 (4) | −0.0072 (4) |
C7 | 0.0534 (7) | 0.0417 (6) | 0.0442 (6) | −0.0067 (5) | 0.0025 (5) | −0.0065 (5) |
C8 | 0.0644 (10) | 0.0504 (8) | 0.0862 (11) | 0.0030 (7) | 0.0051 (8) | −0.0307 (8) |
C9 | 0.0839 (13) | 0.0477 (9) | 0.1221 (17) | 0.0050 (8) | −0.0087 (12) | −0.0170 (9) |
C10 | 0.0620 (8) | 0.0391 (6) | 0.0384 (6) | −0.0151 (5) | 0.0069 (5) | −0.0099 (4) |
C11 | 0.0490 (7) | 0.0375 (5) | 0.0353 (5) | −0.0085 (5) | 0.0015 (5) | −0.0061 (4) |
C12 | 0.0506 (7) | 0.0459 (6) | 0.0354 (6) | −0.0084 (5) | −0.0033 (5) | −0.0043 (5) |
C13 | 0.0659 (10) | 0.0592 (9) | 0.0648 (9) | 0.0140 (7) | −0.0140 (7) | −0.0106 (7) |
C14 | 0.0472 (6) | 0.0359 (5) | 0.0366 (5) | −0.0041 (4) | 0.0007 (5) | −0.0059 (4) |
C15 | 0.0462 (6) | 0.0352 (5) | 0.0372 (5) | −0.0057 (4) | −0.0009 (5) | −0.0061 (4) |
C16 | 0.0410 (6) | 0.0471 (6) | 0.0335 (5) | −0.0054 (5) | −0.0007 (4) | −0.0065 (4) |
C17 | 0.0480 (7) | 0.0451 (6) | 0.0351 (5) | −0.0096 (5) | −0.0041 (5) | −0.0021 (4) |
C18 | 0.0460 (7) | 0.0378 (6) | 0.0463 (6) | −0.0065 (5) | −0.0064 (5) | −0.0064 (5) |
C19 | 0.0440 (7) | 0.0520 (7) | 0.0676 (9) | −0.0015 (5) | 0.0100 (6) | 0.0019 (6) |
C20 | 0.0522 (8) | 0.0474 (7) | 0.0569 (8) | −0.0064 (6) | 0.0117 (6) | 0.0063 (6) |
C21 | 0.0512 (7) | 0.0462 (7) | 0.0557 (8) | −0.0027 (5) | −0.0115 (6) | −0.0029 (6) |
C22 | 0.0629 (9) | 0.0505 (8) | 0.0788 (10) | 0.0062 (7) | −0.0115 (8) | −0.0145 (7) |
O1 | 0.0969 (9) | 0.0419 (5) | 0.0657 (7) | −0.0109 (5) | 0.0071 (6) | −0.0030 (5) |
O2 | 0.0641 (6) | 0.0391 (5) | 0.0563 (5) | −0.0010 (4) | 0.0073 (5) | −0.0149 (4) |
O3 | 0.0526 (5) | 0.0433 (4) | 0.0317 (4) | −0.0127 (3) | 0.0005 (3) | −0.0090 (3) |
O4 | 0.0754 (8) | 0.0890 (8) | 0.0372 (5) | 0.0058 (6) | −0.0124 (5) | −0.0039 (5) |
O5 | 0.0704 (7) | 0.0530 (5) | 0.0423 (5) | 0.0145 (5) | −0.0087 (4) | −0.0085 (4) |
C1—C2 | 1.366 (2) | C11—C12 | 1.4829 (17) |
C1—C6 | 1.3969 (17) | C12—O4 | 1.1990 (15) |
C1—H1 | 0.9300 | C12—O5 | 1.3347 (16) |
C2—C3 | 1.382 (2) | C13—O5 | 1.4370 (16) |
C2—H2 | 0.9300 | C13—H13A | 0.9600 |
C3—C4 | 1.3882 (18) | C13—H13B | 0.9600 |
C3—H3 | 0.9300 | C13—H13C | 0.9600 |
C4—O2 | 1.3632 (15) | C14—C15 | 1.4696 (15) |
C4—C5 | 1.4019 (16) | C14—H14 | 0.9300 |
C5—O3 | 1.3771 (13) | C15—C20 | 1.3905 (18) |
C5—C6 | 1.3901 (16) | C15—C16 | 1.3908 (16) |
C6—C7 | 1.4763 (17) | C16—C17 | 1.3856 (16) |
C7—O1 | 1.1978 (16) | C16—H16 | 0.9300 |
C7—H7 | 0.9300 | C17—C18 | 1.3785 (18) |
C8—O2 | 1.4259 (16) | C17—H17 | 0.9300 |
C8—C9 | 1.488 (3) | C18—C19 | 1.3901 (19) |
C8—H8A | 0.9700 | C18—C21 | 1.5106 (17) |
C8—H8B | 0.9700 | C19—C20 | 1.3853 (19) |
C9—H9A | 0.9600 | C19—H19 | 0.9300 |
C9—H9B | 0.9600 | C20—H20 | 0.9300 |
C9—H9C | 0.9600 | C21—C22 | 1.509 (2) |
C10—O3 | 1.4520 (15) | C21—H21A | 0.9700 |
C10—C11 | 1.4949 (16) | C21—H21B | 0.9700 |
C10—H10A | 0.9700 | C22—H22A | 0.9600 |
C10—H10B | 0.9700 | C22—H22B | 0.9600 |
C11—C14 | 1.3414 (16) | C22—H22C | 0.9600 |
C2—C1—C6 | 119.61 (12) | O5—C12—C11 | 113.84 (10) |
C2—C1—H1 | 120.2 | O5—C13—H13A | 109.5 |
C6—C1—H1 | 120.2 | O5—C13—H13B | 109.5 |
C1—C2—C3 | 121.00 (12) | H13A—C13—H13B | 109.5 |
C1—C2—H2 | 119.5 | O5—C13—H13C | 109.5 |
C3—C2—H2 | 119.5 | H13A—C13—H13C | 109.5 |
C2—C3—C4 | 120.52 (12) | H13B—C13—H13C | 109.5 |
C2—C3—H3 | 119.7 | C11—C14—C15 | 127.62 (11) |
C4—C3—H3 | 119.7 | C11—C14—H14 | 116.2 |
O2—C4—C3 | 125.90 (11) | C15—C14—H14 | 116.2 |
O2—C4—C5 | 115.38 (10) | C20—C15—C16 | 117.66 (11) |
C3—C4—C5 | 118.72 (12) | C20—C15—C14 | 124.35 (11) |
O3—C5—C6 | 119.47 (10) | C16—C15—C14 | 117.99 (11) |
O3—C5—C4 | 120.26 (10) | C17—C16—C15 | 121.10 (11) |
C6—C5—C4 | 120.17 (10) | C17—C16—H16 | 119.4 |
C5—C6—C1 | 119.87 (11) | C15—C16—H16 | 119.4 |
C5—C6—C7 | 119.81 (10) | C18—C17—C16 | 121.16 (11) |
C1—C6—C7 | 120.32 (11) | C18—C17—H17 | 119.4 |
O1—C7—C6 | 124.82 (12) | C16—C17—H17 | 119.4 |
O1—C7—H7 | 117.6 | C17—C18—C19 | 117.90 (11) |
C6—C7—H7 | 117.6 | C17—C18—C21 | 121.17 (11) |
O2—C8—C9 | 107.34 (15) | C19—C18—C21 | 120.94 (12) |
O2—C8—H8A | 110.2 | C20—C19—C18 | 121.21 (13) |
C9—C8—H8A | 110.2 | C20—C19—H19 | 119.4 |
O2—C8—H8B | 110.2 | C18—C19—H19 | 119.4 |
C9—C8—H8B | 110.2 | C19—C20—C15 | 120.81 (12) |
H8A—C8—H8B | 108.5 | C19—C20—H20 | 119.6 |
C8—C9—H9A | 109.5 | C15—C20—H20 | 119.6 |
C8—C9—H9B | 109.5 | C22—C21—C18 | 113.21 (12) |
H9A—C9—H9B | 109.5 | C22—C21—H21A | 108.9 |
C8—C9—H9C | 109.5 | C18—C21—H21A | 108.9 |
H9A—C9—H9C | 109.5 | C22—C21—H21B | 108.9 |
H9B—C9—H9C | 109.5 | C18—C21—H21B | 108.9 |
O3—C10—C11 | 108.76 (10) | H21A—C21—H21B | 107.7 |
O3—C10—H10A | 109.9 | C21—C22—H22A | 109.5 |
C11—C10—H10A | 109.9 | C21—C22—H22B | 109.5 |
O3—C10—H10B | 109.9 | H22A—C22—H22B | 109.5 |
C11—C10—H10B | 109.9 | C21—C22—H22C | 109.5 |
H10A—C10—H10B | 108.3 | H22A—C22—H22C | 109.5 |
C14—C11—C12 | 120.99 (11) | H22B—C22—H22C | 109.5 |
C14—C11—C10 | 125.04 (11) | C4—O2—C8 | 118.22 (11) |
C12—C11—C10 | 113.86 (10) | C5—O3—C10 | 114.56 (9) |
O4—C12—O5 | 122.44 (12) | C12—O5—C13 | 115.99 (11) |
O4—C12—C11 | 123.71 (12) | ||
C6—C1—C2—C3 | 2.1 (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—O2 | 177.56 (13) | C11—C14—C15—C16 | 141.38 (14) |
C2—C3—C4—C5 | −1.9 (2) | C20—C15—C16—C17 | 4.00 (19) |
O2—C4—C5—O3 | 0.58 (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—C6 | 3.65 (18) | C16—C17—C18—C21 | 179.52 (12) |
O3—C5—C6—C1 | −179.04 (11) | C17—C18—C19—C20 | 3.1 (2) |
C4—C5—C6—C1 | −2.56 (18) | C21—C18—C19—C20 | −177.14 (14) |
O3—C5—C6—C7 | 0.21 (18) | C18—C19—C20—C15 | −1.9 (3) |
C4—C5—C6—C7 | 176.69 (11) | C16—C15—C20—C19 | −1.6 (2) |
C2—C1—C6—C5 | −0.3 (2) | C14—C15—C20—C19 | 178.41 (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—C22 | 61.87 (19) |
C1—C6—C7—O1 | 10.3 (2) | C3—C4—O2—C8 | −12.8 (2) |
O3—C10—C11—C14 | 103.91 (14) | C5—C4—O2—C8 | 166.63 (12) |
O3—C10—C11—C12 | −79.81 (13) | C9—C8—O2—C4 | −169.18 (14) |
C14—C11—C12—O4 | 176.44 (14) | C6—C5—O3—C10 | −119.28 (12) |
C10—C11—C12—O4 | 0.0 (2) | C4—C5—O3—C10 | 64.25 (14) |
C14—C11—C12—O5 | −3.89 (18) | C11—C10—O3—C5 | 135.17 (10) |
C10—C11—C12—O5 | 179.67 (11) | O4—C12—O5—C13 | −3.1 (2) |
C12—C11—C14—C15 | −179.59 (12) | C11—C12—O5—C13 | 177.20 (13) |
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. |
Experimental details
Crystal data | |
Chemical formula | C22H24O5 |
Mr | 368.41 |
Crystal system, space group | Triclinic, 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) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25506, 6646, 4400 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.740 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.164, 1.02 |
No. of reflections | 6646 |
No. of parameters | 247 |
H-atom treatment | H-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).
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. |
Acknowledgements
RG and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the
data collection and Dr V. Murugan, Head of the Department of Physics, for providing facilities in the department to carry out this work.References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
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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)