Literature DB >> 22065120

(Z)-Methyl 2-[(4-bromo-2-formyl-phen-oxy)meth-yl]-3-o-tolyl-acrylate.

S Vijayakumar, R Madhanraj, S Murugavel, R Selvakumar, M Bakthadoss.   

Abstract

In the title compound, C(19)H(17)BrO(4), the dihedral angle between the two benzene rings is 82.1 (1)°. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond which generates an S(7) ring motif. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions. Inter-molecular C-H⋯O inter-actions are involved in the formation of centrosymmetric R(2) (2)(16) dimers, which are connected into supra-molecular tapes running along the [100] direction.

Entities:  

Year:  2011        PMID： 22065120      PMCID： PMC3201264          DOI： 10.1107/S1600536811037731

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to the applications of acrylates, see: de Fraine et al. (1991 ▶); Zhang & Ji (1992 ▶). For related structures, see: Wang et al. (2011 ▶); Hou (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H17BrO4 M = 389.24 Triclinic, a = 8.0114 (2) Å b = 8.6138 (2) Å c = 13.4827 (4) Å α = 96.466 (1)° β = 97.185 (1)° γ = 106.546 (2)° V = 874.08 (4) Å3 Z = 2 Mo Kα radiation μ = 2.37 mm−1 T = 293 K 0.25 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.547, T max = 0.653 21788 measured reflections 5440 independent reflections 2870 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.125 S = 1.02 5440 reflections 219 parameters H-atom parameters constrained Δρmax = 0.61 e Å−3 Δρmin = −0.61 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037731/bt5640sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037731/bt5640Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811037731/bt5640Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H17BrO4Z = 2
Mr = 389.24F(000) = 396
Triclinic, P1Dx = 1.479 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0114 (2) ÅCell parameters from 5491 reflections
b = 8.6138 (2) Åθ = 1.5–30.8°
c = 13.4827 (4) ŵ = 2.37 mm−1
α = 96.466 (1)°T = 293 K
β = 97.185 (1)°Block, colourless
γ = 106.546 (2)°0.25 × 0.23 × 0.18 mm
V = 874.08 (4) Å3
Bruker APEXII CCD diffractometer5440 independent reflections
Radiation source: fine-focus sealed tube2870 reflections with I > 2σ(I)
graphiteRint = 0.025
Detector resolution: 10.0 pixels mm-1θmax = 30.8°, θmin = 2.5°
ω scansh = −11→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −9→12
Tmin = 0.547, Tmax = 0.653l = −19→19
21788 measured reflections
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) = 0.125H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2207P] where P = (Fo2 + 2Fc2)/3
5440 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.61 e Å−3
0 restraintsΔρmin = −0.61 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
xyzUiso*/Ueq
C10.5938 (3)0.6570 (2)0.44131 (14)0.0451 (4)
C20.6433 (3)0.7625 (3)0.53364 (16)0.0582 (6)
H20.55810.79440.56440.070*
C30.8167 (4)0.8193 (3)0.57901 (16)0.0628 (6)
C40.9439 (3)0.7725 (3)0.53421 (17)0.0620 (6)
H41.06140.81240.56540.074*
C50.8989 (3)0.6674 (3)0.44374 (16)0.0522 (5)
H50.98530.63600.41400.063*
C60.7237 (2)0.6087 (2)0.39719 (14)0.0419 (4)
C70.7942 (2)0.4478 (2)0.26070 (15)0.0460 (4)
H7A0.86290.40460.30860.055*
H7B0.87410.53750.23640.055*
C80.6943 (3)0.3164 (2)0.17415 (15)0.0462 (4)
C90.6192 (3)0.1482 (3)0.19567 (16)0.0514 (5)
C100.5959 (4)−0.0215 (3)0.3216 (2)0.0829 (8)
H10A0.4703−0.06460.30090.124*
H10B0.6242−0.01470.39360.124*
H10C0.6521−0.09250.28850.124*
C110.4093 (3)0.6015 (3)0.39152 (18)0.0588 (6)
H110.37840.52370.33330.071*
C120.6729 (3)0.3375 (3)0.07702 (15)0.0494 (5)
H120.61700.24310.03040.059*
C130.7263 (2)0.4903 (3)0.03471 (15)0.0490 (5)
C140.7153 (3)0.6369 (3)0.08434 (18)0.0598 (5)
H140.67510.63850.14610.072*
C150.7630 (4)0.7799 (3)0.0434 (2)0.0711 (7)
H150.75540.87700.07750.085*
C160.8218 (4)0.7776 (3)−0.0476 (2)0.0743 (7)
H160.85660.8742−0.07470.089*
C170.8297 (3)0.6337 (3)−0.09913 (18)0.0651 (6)
H170.86730.6340−0.16170.078*
C180.7828 (3)0.4878 (3)−0.06005 (15)0.0531 (5)
C190.7942 (3)0.3325 (3)−0.11804 (17)0.0655 (6)
H19A0.82740.3532−0.18240.098*
H19B0.68140.2499−0.12830.098*
H19C0.88100.2951−0.08040.098*
O10.5339 (3)0.0321 (2)0.13521 (13)0.0794 (5)
O20.6575 (2)0.13951 (18)0.29434 (12)0.0652 (4)
O30.66638 (17)0.50451 (17)0.30849 (10)0.0497 (3)
O40.2955 (2)0.6501 (3)0.42096 (16)0.0877 (6)
Br10.88459 (5)0.96282 (4)0.70416 (2)0.10598 (18)
U11U22U33U12U13U23
C10.0500 (11)0.0487 (11)0.0443 (10)0.0191 (9)0.0157 (9)0.0186 (8)
C20.0751 (16)0.0628 (13)0.0495 (11)0.0316 (12)0.0236 (11)0.0185 (10)
C30.0861 (18)0.0606 (13)0.0405 (10)0.0204 (12)0.0117 (11)0.0069 (9)
C40.0599 (13)0.0636 (14)0.0521 (12)0.0087 (11)−0.0021 (10)0.0051 (10)
C50.0449 (11)0.0578 (12)0.0510 (11)0.0123 (10)0.0073 (9)0.0060 (9)
C60.0445 (10)0.0420 (10)0.0391 (9)0.0107 (8)0.0080 (8)0.0116 (8)
C70.0394 (10)0.0467 (10)0.0528 (11)0.0139 (8)0.0105 (8)0.0051 (8)
C80.0423 (10)0.0476 (11)0.0491 (11)0.0139 (9)0.0104 (8)0.0048 (8)
C90.0536 (12)0.0490 (11)0.0504 (11)0.0142 (10)0.0107 (9)0.0035 (9)
C100.106 (2)0.0545 (14)0.0797 (18)0.0085 (14)0.0066 (15)0.0254 (13)
C110.0498 (12)0.0710 (14)0.0669 (14)0.0253 (11)0.0187 (11)0.0282 (12)
C120.0434 (10)0.0529 (12)0.0499 (11)0.0135 (9)0.0078 (9)0.0027 (9)
C130.0396 (10)0.0567 (12)0.0482 (11)0.0134 (9)0.0021 (8)0.0073 (9)
C140.0595 (13)0.0647 (14)0.0619 (13)0.0268 (11)0.0123 (11)0.0137 (11)
C150.0777 (16)0.0630 (15)0.0803 (18)0.0342 (13)0.0083 (14)0.0139 (13)
C160.0793 (17)0.0678 (16)0.0757 (17)0.0188 (14)0.0051 (14)0.0284 (14)
C170.0607 (14)0.0744 (16)0.0530 (13)0.0085 (12)0.0033 (10)0.0187 (12)
C180.0398 (10)0.0650 (13)0.0457 (11)0.0067 (10)−0.0025 (8)0.0072 (10)
C190.0609 (14)0.0723 (15)0.0493 (12)0.0043 (12)0.0074 (10)−0.0049 (11)
O10.1097 (14)0.0511 (9)0.0574 (9)0.0001 (9)0.0075 (9)−0.0037 (8)
O20.0781 (11)0.0482 (9)0.0593 (9)0.0066 (8)−0.0001 (8)0.0129 (7)
O30.0386 (7)0.0575 (8)0.0496 (8)0.0131 (6)0.0068 (6)−0.0009 (6)
O40.0632 (11)0.1185 (16)0.1058 (15)0.0513 (11)0.0325 (10)0.0350 (12)
Br10.1485 (4)0.1068 (3)0.05066 (17)0.0334 (2)0.00845 (17)−0.01403 (15)
C1—C21.396 (3)C10—H10A0.9600
C1—C61.398 (3)C10—H10B0.9600
C1—C111.464 (3)C10—H10C0.9600
C2—C31.370 (3)C11—O41.197 (3)
C2—H20.9300C11—H110.9300
C3—C41.378 (3)C12—C131.466 (3)
C3—Br11.895 (2)C12—H120.9300
C4—C51.376 (3)C13—C141.392 (3)
C4—H40.9300C13—C181.408 (3)
C5—C61.387 (3)C14—C151.380 (3)
C5—H50.9300C14—H140.9300
C6—O31.354 (2)C15—C161.369 (4)
C7—O31.443 (2)C15—H150.9300
C7—C81.496 (3)C16—C171.373 (4)
C7—H7A0.9700C16—H160.9300
C7—H7B0.9700C17—C181.389 (3)
C8—C121.339 (3)C17—H170.9300
C8—C91.478 (3)C18—C191.504 (3)
C9—O11.191 (3)C19—H19A0.9600
C9—O21.343 (3)C19—H19B0.9600
C10—O21.440 (3)C19—H19C0.9600
C2—C1—C6118.86 (19)H10A—C10—H10C109.5
C2—C1—C11119.93 (19)H10B—C10—H10C109.5
C6—C1—C11121.20 (19)O4—C11—C1124.1 (2)
C3—C2—C1120.2 (2)O4—C11—H11117.9
C3—C2—H2119.9C1—C11—H11117.9
C1—C2—H2119.9C8—C12—C13128.39 (19)
C2—C3—C4120.4 (2)C8—C12—H12115.8
C2—C3—Br1120.44 (18)C13—C12—H12115.8
C4—C3—Br1119.17 (19)C14—C13—C18119.1 (2)
C5—C4—C3120.6 (2)C14—C13—C12121.34 (19)
C5—C4—H4119.7C18—C13—C12119.46 (19)
C3—C4—H4119.7C15—C14—C13121.1 (2)
C4—C5—C6119.5 (2)C15—C14—H14119.4
C4—C5—H5120.2C13—C14—H14119.4
C6—C5—H5120.2C16—C15—C14119.5 (2)
O3—C6—C5123.87 (17)C16—C15—H15120.2
O3—C6—C1115.80 (17)C14—C15—H15120.2
C5—C6—C1120.33 (18)C15—C16—C17120.4 (2)
O3—C7—C8107.34 (15)C15—C16—H16119.8
O3—C7—H7A110.2C17—C16—H16119.8
C8—C7—H7A110.2C16—C17—C18121.5 (2)
O3—C7—H7B110.2C16—C17—H17119.2
C8—C7—H7B110.2C18—C17—H17119.2
H7A—C7—H7B108.5C17—C18—C13118.2 (2)
C12—C8—C9116.79 (19)C17—C18—C19120.2 (2)
C12—C8—C7124.91 (19)C13—C18—C19121.5 (2)
C9—C8—C7118.25 (18)C18—C19—H19A109.5
O1—C9—O2122.5 (2)C18—C19—H19B109.5
O1—C9—C8125.9 (2)H19A—C19—H19B109.5
O2—C9—C8111.64 (18)C18—C19—H19C109.5
O2—C10—H10A109.5H19A—C19—H19C109.5
O2—C10—H10B109.5H19B—C19—H19C109.5
H10A—C10—H10B109.5C9—O2—C10115.46 (19)
O2—C10—H10C109.5C6—O3—C7118.17 (15)
C6—C1—C2—C31.0 (3)C9—C8—C12—C13177.09 (19)
C11—C1—C2—C3−177.82 (19)C7—C8—C12—C13−5.6 (3)
C1—C2—C3—C4−0.2 (3)C8—C12—C13—C14−37.2 (3)
C1—C2—C3—Br1179.89 (15)C8—C12—C13—C18145.6 (2)
C2—C3—C4—C5−0.5 (4)C18—C13—C14—C15−1.7 (3)
Br1—C3—C4—C5179.47 (17)C12—C13—C14—C15−179.0 (2)
C3—C4—C5—C60.3 (3)C13—C14—C15—C160.2 (4)
C4—C5—C6—O3−179.72 (19)C14—C15—C16—C171.4 (4)
C4—C5—C6—C10.5 (3)C15—C16—C17—C18−1.5 (4)
C2—C1—C6—O3179.09 (17)C16—C17—C18—C130.0 (3)
C11—C1—C6—O3−2.1 (3)C16—C17—C18—C19−179.6 (2)
C2—C1—C6—C5−1.2 (3)C14—C13—C18—C171.5 (3)
C11—C1—C6—C5177.62 (19)C12—C13—C18—C17178.89 (19)
O3—C7—C8—C12100.2 (2)C14—C13—C18—C19−178.89 (19)
O3—C7—C8—C9−82.5 (2)C12—C13—C18—C19−1.5 (3)
C12—C8—C9—O1−4.1 (3)O1—C9—O2—C102.9 (3)
C7—C8—C9—O1178.4 (2)C8—C9—O2—C10−177.5 (2)
C12—C8—C9—O2176.27 (18)C5—C6—O3—C71.6 (3)
C7—C8—C9—O2−1.2 (3)C1—C6—O3—C7−178.66 (16)
C2—C1—C11—O45.7 (3)C8—C7—O3—C6171.39 (15)
C6—C1—C11—O4−173.0 (2)
D—H···AD—HH···AD···AD—H···A
C14—H14···O30.932.593.377 (3)143
C19—H19B···O1i0.962.533.436 (3)157
C5—H5···O4ii0.932.443.273 (3)149
C19—H19C···Cgiii0.962.743.580 (3)147
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 benzene ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C14—H14⋯O30.932.593.377 (3)143
C19—H19B⋯O1i0.962.533.436 (3)157
C5—H5⋯O4ii0.932.443.273 (3)149
C19—H19C⋯Cgiii0.962.743.580 (3)147

Symmetry codes: (i) ; (ii) ; (iii) .

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