PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. Jun 1, 2012; 68(Pt 6): o1617.
Published online May 5, 2012. doi:  10.1107/S1600536812019046
PMCID: PMC3379223
Methyl (E)-2-({2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-(4-methyl­phen­yl)acrylate
G. Ganesh,a J. Srinivasan,b E. Govindan,c M. Bakthadoss,b and A. SubbiahPandic*
aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India
bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
Correspondence e-mail: a_sp59/at/yahoo.in
Received April 20, 2012; Accepted April 27, 2012.
Abstract
In the title compound, C19H19NO4, the dihedral angle between the mean planes through the benzene rings is 82.18 (7)°. The C=N double bond is trans-configured. The mol­ecules are linked into centrosymmetric dimers via pairs of O—H(...)N hydrogen bonds with the motif R 2 2(6). The crystal packing also features C—H(...)O inter­actions. The methyl group attached to one of the aromatic rings is disordered over two almost equally occupied positions [occpancy ratio = 0.51 (4):0.49 (4)].
Related literature  
For information on oximes, see: Chaudhuri (2003 [triangle]). For a related structure, see: SakthiMurugesan et al. (2011 [triangle]).
An external file that holds a picture, illustration, etc.
Object name is e-68-o1617-scheme1.jpg Object name is e-68-o1617-scheme1.jpg
Crystal data  
  • C19H19NO4
  • M r = 325.35
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o1617-efi2.jpg
  • a = 8.8683 (2) Å
  • b = 9.3246 (2) Å
  • c = 11.9259 (3) Å
  • α = 75.200 (2)°
  • β = 76.453 (2)°
  • γ = 65.142 (1)°
  • V = 856.04 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.35 × 0.30 × 0.25 mm
Data collection  
  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.970, T max = 0.978
  • 20292 measured reflections
  • 4580 independent reflections
  • 3493 reflections with I > 2σ(I)
  • R int = 0.022
Refinement  
  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.132
  • S = 1.04
  • 4580 reflections
  • 221 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.20 e Å−3
Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON.
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019046/bt5884sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019046/bt5884Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812019046/bt5884Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India for the data collection.
supplementary crystallographic information
Comment
Oximes are a classical type of chelating ligands which are widely used in coordination and analytical chemistry (Chaudhuri, 2003). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.
X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles in (Fig. 1) agree with those observed in other acrylate derivatives (SakthiMurugesan et al., 2011). the whole molecule is not planar as the dihedral angle between the two phenyl rings is 82.18 (7)°, it shows that both the rings are almost perpendicular to each other. The methoxybutene group connects the two phenyl rings, results in twisting the rings and placed those rings in perpendicular direction. The oxime group having the C═N forming an E configuration. The atom C19 is deviated by -0.037 (2) Å from the least squares plane of the C13—C18 ring. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being -0.008 (1) Å for the C2 atom.
The enoate group assumes an extended conformation as can be seen from torsion angles C8—C9—C10—O3 [169.97 (15)°] and C9—C10—O4—C11 [179.55 (14)°]. The hydroxyethanimine group in the molecules are linked into cyclic centrosymmetric dimers via O—H···N hydrogen bonds with the motif R22(6). In addition to van der Waals interactions the crystal packing is stabilized by C–H..O and O–H···N interactions.
Experimental
To a stirred solution of (E)-methyl 2-((2-formylphenoxy)methyl)-3 - p-tolyacrylate (4 mmol) in 10 ml of EtOH/H2O mixture(1:1) was added NH2OH.HCl(6 mmol) in the presence of 50% NaOH at room temperature. Then the reaction mixture was allowed to stir at room temperature For 1.5 h. After completion of the reaction, solvent was removed and crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3x15ml). The combined organic layer was washed with brine (2x10ml) and dried over anhydrous Na2SO4 and then evaporated under reduced pressure to obtain(E)-methyl 2-((2-((E)-(hydroxyimino) methyl)phenoxy) methyl)-3-p-tolylacrylate as a colourless solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.
Refinement
All H atoms were fixed geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å and an O—H distance of 0.82 Å and with Uiso(H) = 1.5Ueq(Cmethyl, O) or 1.2Ueq(C) for other H atoms.
Figures
Fig. 1.
Fig. 1.
View of the title molecule with the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level while the H atoms are shown as small spheres of arbitrary radii.
Fig. 2.
Fig. 2.
The crystal structure showing the centrosymmetric hydrogen bond motif R22(6). For the sake of clarity, the H atoms not involved in the motif have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (2 - x, -y, 1 - z). The (more ...)
Crystal data
C19H19NO4Z = 2
Mr = 325.35F(000) = 344
Triclinic, P1Dx = 1.262 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8683 (2) ÅCell parameters from 6056 reflections
b = 9.3246 (2) Åθ = 2.5–32.5°
c = 11.9259 (3) ŵ = 0.09 mm1
α = 75.200 (2)°T = 293 K
β = 76.453 (2)°Block, white crystalline
γ = 65.142 (1)°0.35 × 0.30 × 0.25 mm
V = 856.04 (3) Å3
Data collection
Bruker APEXII CCD area-detector diffractometer4580 independent reflections
Radiation source: fine-focus sealed tube3493 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω and [var phi] scansθmax = 29.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.970, Tmax = 0.978k = −12→12
20292 measured reflectionsl = −16→16
Refinement
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0596P)2 + 0.1563P] where P = (Fo2 + 2Fc2)/3
4580 reflections(Δ/σ)max < 0.001
221 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.20 e Å3
Special details
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)
xyzUiso*/UeqOcc. (<1)
C10.30137 (15)0.78709 (15)0.40342 (11)0.0446 (3)
H10.38390.82440.36070.053*
C20.32860 (14)0.61892 (14)0.41323 (10)0.0397 (3)
C30.24555 (17)0.54149 (16)0.50493 (12)0.0521 (3)
H30.17010.59770.56230.063*
C40.2729 (2)0.38274 (18)0.51246 (13)0.0608 (4)
H40.21610.33250.57430.073*
C50.38495 (19)0.29887 (16)0.42785 (13)0.0569 (3)
H50.40270.19200.43260.068*
C60.47131 (16)0.37155 (15)0.33607 (12)0.0476 (3)
H60.54700.31390.27950.057*
C70.44431 (14)0.53102 (13)0.32886 (10)0.0385 (2)
C80.64247 (16)0.53394 (14)0.15207 (11)0.0450 (3)
H8A0.58490.51350.10170.054*
H8B0.72250.43200.18590.054*
C90.73103 (15)0.64103 (15)0.08311 (11)0.0441 (3)
C100.89857 (17)0.60977 (17)0.11066 (13)0.0532 (3)
C111.0978 (2)0.4600 (3)0.24022 (17)0.0852 (6)
H11A1.18010.45650.17130.128*
H11B1.13070.35710.29080.128*
H11C1.08990.54020.28070.128*
C120.67354 (16)0.76491 (15)−0.00294 (11)0.0475 (3)
H120.74500.8193−0.03590.057*
C130.51907 (16)0.82972 (14)−0.05413 (11)0.0456 (3)
C140.37187 (17)0.80613 (17)−0.00162 (12)0.0546 (3)
H140.36630.74670.07370.065*
C150.23412 (19)0.86949 (18)−0.05950 (14)0.0594 (4)
H150.13780.8506−0.02280.071*
C160.23571 (19)0.96063 (17)−0.17098 (13)0.0578 (4)
C170.3798 (2)0.98842 (18)−0.22200 (13)0.0619 (4)
H170.38331.0512−0.29620.074*
C180.51779 (19)0.92530 (16)−0.16541 (12)0.0558 (3)
H180.61290.9466−0.20200.067*
C190.0852 (3)1.0257 (3)−0.23393 (18)0.0884 (6)
H19A0.00300.9840−0.18860.133*0.51 (4)
H19B0.11920.9937−0.30930.133*0.51 (4)
H19C0.03761.1408−0.24400.133*0.51 (4)
H19D0.06180.9382−0.24330.133*0.49 (4)
H19F0.10821.0858−0.30960.133*0.49 (4)
H19E−0.01021.0945−0.18900.133*0.49 (4)
N10.16707 (14)0.88269 (13)0.45217 (10)0.0493 (3)
O10.16721 (14)1.03758 (12)0.43411 (11)0.0699 (3)
H1A0.07661.09770.46350.105*
O20.52349 (11)0.61418 (10)0.24323 (7)0.0467 (2)
O30.99150 (15)0.67203 (16)0.05342 (13)0.0872 (4)
O40.93678 (13)0.49931 (16)0.20693 (9)0.0720 (3)
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
C10.0417 (6)0.0459 (6)0.0413 (6)−0.0165 (5)0.0028 (5)−0.0081 (5)
C20.0363 (5)0.0416 (6)0.0369 (5)−0.0131 (4)−0.0052 (4)−0.0034 (4)
C30.0498 (7)0.0526 (7)0.0433 (6)−0.0177 (6)0.0034 (5)−0.0034 (5)
C40.0628 (9)0.0551 (8)0.0556 (8)−0.0281 (7)0.0009 (7)0.0061 (6)
C50.0620 (8)0.0428 (6)0.0639 (8)−0.0235 (6)−0.0082 (7)−0.0009 (6)
C60.0480 (7)0.0427 (6)0.0502 (7)−0.0160 (5)−0.0055 (5)−0.0095 (5)
C70.0366 (5)0.0407 (6)0.0362 (5)−0.0144 (4)−0.0063 (4)−0.0032 (4)
C80.0453 (6)0.0428 (6)0.0431 (6)−0.0146 (5)0.0033 (5)−0.0141 (5)
C90.0415 (6)0.0467 (6)0.0424 (6)−0.0162 (5)0.0055 (5)−0.0172 (5)
C100.0449 (7)0.0574 (7)0.0560 (8)−0.0177 (6)0.0030 (6)−0.0205 (6)
C110.0524 (9)0.1224 (16)0.0710 (11)−0.0173 (10)−0.0144 (8)−0.0242 (11)
C120.0462 (7)0.0483 (6)0.0483 (7)−0.0221 (5)0.0060 (5)−0.0136 (5)
C130.0499 (7)0.0404 (6)0.0446 (6)−0.0181 (5)0.0019 (5)−0.0110 (5)
C140.0515 (7)0.0568 (7)0.0484 (7)−0.0215 (6)−0.0001 (6)−0.0027 (6)
C150.0504 (8)0.0629 (8)0.0635 (9)−0.0243 (7)−0.0030 (6)−0.0091 (7)
C160.0623 (9)0.0521 (7)0.0576 (8)−0.0157 (6)−0.0123 (7)−0.0148 (6)
C170.0745 (10)0.0535 (8)0.0487 (7)−0.0211 (7)−0.0075 (7)−0.0017 (6)
C180.0600 (8)0.0490 (7)0.0534 (8)−0.0246 (6)0.0010 (6)−0.0029 (6)
C190.0806 (13)0.1011 (15)0.0808 (12)−0.0241 (11)−0.0337 (10)−0.0105 (11)
N10.0485 (6)0.0423 (5)0.0524 (6)−0.0168 (4)0.0037 (5)−0.0118 (5)
O10.0685 (7)0.0460 (5)0.0879 (8)−0.0241 (5)0.0180 (6)−0.0223 (5)
O20.0513 (5)0.0418 (4)0.0421 (4)−0.0193 (4)0.0095 (4)−0.0118 (3)
O30.0586 (7)0.0883 (9)0.1159 (11)−0.0418 (6)−0.0146 (7)0.0059 (8)
O40.0507 (6)0.1054 (9)0.0517 (6)−0.0264 (6)−0.0068 (5)−0.0074 (6)
Geometric parameters (Å, º)
C1—N11.2644 (16)C11—H11B0.9600
C1—C21.4602 (17)C11—H11C0.9600
C1—H10.9300C12—C131.4566 (19)
C2—C31.3879 (17)C12—H120.9300
C2—C71.4027 (16)C13—C141.3902 (18)
C3—C41.378 (2)C13—C181.3964 (18)
C3—H30.9300C14—C151.378 (2)
C4—C51.377 (2)C14—H140.9300
C4—H40.9300C15—C161.383 (2)
C5—C61.3815 (19)C15—H150.9300
C5—H50.9300C16—C171.380 (2)
C6—C71.3860 (17)C16—C191.506 (2)
C6—H60.9300C17—C181.370 (2)
C7—O21.3618 (14)C17—H170.9300
C8—O21.4386 (14)C18—H180.9300
C8—C91.4925 (17)C19—H19A0.9600
C8—H8A0.9700C19—H19B0.9600
C8—H8B0.9700C19—H19C0.9600
C9—C121.3386 (18)C19—H19D0.9600
C9—C101.4886 (19)C19—H19F0.9600
C10—O31.1910 (17)C19—H19E0.9600
C10—O41.3336 (18)N1—O11.4052 (14)
C11—O41.443 (2)O1—H1A0.8200
C11—H11A0.9600
N1—C1—C2120.89 (11)H11A—C11—H11C109.5
N1—C1—H1119.6H11B—C11—H11C109.5
C2—C1—H1119.6C9—C12—C13131.50 (12)
C3—C2—C7118.50 (11)C9—C12—H12114.2
C3—C2—C1122.09 (11)C13—C12—H12114.2
C7—C2—C1119.40 (10)C14—C13—C18116.93 (13)
C4—C3—C2121.16 (13)C14—C13—C12125.81 (12)
C4—C3—H3119.4C18—C13—C12117.26 (12)
C2—C3—H3119.4C15—C14—C13121.00 (13)
C5—C4—C3119.61 (13)C15—C14—H14119.5
C5—C4—H4120.2C13—C14—H14119.5
C3—C4—H4120.2C14—C15—C16121.55 (14)
C4—C5—C6120.81 (13)C14—C15—H15119.2
C4—C5—H5119.6C16—C15—H15119.2
C6—C5—H5119.6C17—C16—C15117.63 (14)
C5—C6—C7119.55 (12)C17—C16—C19121.61 (15)
C5—C6—H6120.2C15—C16—C19120.76 (16)
C7—C6—H6120.2C18—C17—C16121.27 (14)
O2—C7—C6124.60 (11)C18—C17—H17119.4
O2—C7—C2115.05 (10)C16—C17—H17119.4
C6—C7—C2120.35 (11)C17—C18—C13121.57 (14)
O2—C8—C9107.57 (9)C17—C18—H18119.2
O2—C8—H8A110.2C13—C18—H18119.2
C9—C8—H8A110.2C16—C19—H19A109.5
O2—C8—H8B110.2C16—C19—H19B109.5
C9—C8—H8B110.2C16—C19—H19C109.5
H8A—C8—H8B108.5C16—C19—H19D109.5
C12—C9—C10115.91 (12)C16—C19—H19F109.5
C12—C9—C8125.82 (12)H19D—C19—H19F109.5
C10—C9—C8118.27 (11)C16—C19—H19E109.5
O3—C10—O4122.75 (14)H19D—C19—H19E109.5
O3—C10—C9125.04 (14)H19F—C19—H19E109.5
O4—C10—C9112.19 (12)C1—N1—O1111.94 (11)
O4—C11—H11A109.5N1—O1—H1A109.5
O4—C11—H11B109.5C7—O2—C8118.77 (9)
H11A—C11—H11B109.5C10—O4—C11116.22 (14)
O4—C11—H11C109.5
N1—C1—C2—C3−23.53 (19)C8—C9—C12—C13−0.6 (2)
N1—C1—C2—C7157.62 (12)C9—C12—C13—C1420.6 (2)
C7—C2—C3—C4−1.2 (2)C9—C12—C13—C18−159.99 (14)
C1—C2—C3—C4179.93 (13)C18—C13—C14—C152.5 (2)
C2—C3—C4—C50.2 (2)C12—C13—C14—C15−178.12 (13)
C3—C4—C5—C60.6 (2)C13—C14—C15—C16−0.9 (2)
C4—C5—C6—C7−0.3 (2)C14—C15—C16—C17−1.0 (2)
C5—C6—C7—O2179.27 (12)C14—C15—C16—C19178.59 (15)
C5—C6—C7—C2−0.80 (19)C15—C16—C17—C181.3 (2)
C3—C2—C7—O2−178.54 (11)C19—C16—C17—C18−178.27 (15)
C1—C2—C7—O20.35 (16)C16—C17—C18—C130.3 (2)
C3—C2—C7—C61.53 (17)C14—C13—C18—C17−2.2 (2)
C1—C2—C7—C6−179.59 (11)C12—C13—C18—C17178.37 (13)
O2—C8—C9—C12−82.19 (15)C2—C1—N1—O1178.81 (11)
O2—C8—C9—C1097.89 (12)C6—C7—O2—C80.84 (17)
C12—C9—C10—O3−10.0 (2)C2—C7—O2—C8−179.09 (10)
C8—C9—C10—O3169.98 (14)C9—C8—O2—C7−170.37 (10)
C12—C9—C10—O4171.55 (12)O3—C10—O4—C111.0 (2)
C8—C9—C10—O4−8.52 (16)C9—C10—O4—C11179.55 (13)
C10—C9—C12—C13179.32 (12)
Hydrogen-bond geometry (Å, º)
D—H···AD—HH···AD···AD—H···A
O1—H1A···N1i0.822.112.8211 (15)145
C15—H15···O3ii0.932.403.247 (2)151
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y, z.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5884).
References
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison Wisconsin, USA.
  • Chaudhuri, P. (2003). Coord. Chem. Rev. 243, 143–168.
  • SakthiMurugesan, K., Govindan, E., Srinivasan, J., Bakthadoss, M. & SubbiahPandi, A. (2011). Acta Cryst. E67, o2754. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of
International Union of Crystallography