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The solid-state structure of the title compound, C16H13BrO2, demonstrates an E configuration about the central C=C bond. Symmetry-related mol­ecules are linked by O—H...O hydrogen bonds [O...O = 2.617 (3) Å], forming centrosymmetric carboxylic acid dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026463/lw2016sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026463/lw2016Isup2.hkl
Contains datablock I

CCDC reference: 654922

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](Wave) = 0.000 Å
  • R factor = 0.041
  • wR factor = 0.098
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.222 0.706 Tmin and Tmax expected: 0.198 0.703 RR = 1.118 Please check that your absorption correction is appropriate.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Cinnamic Acid derived antibacterial drugs have increased the importance of these acids, especially halogenated Cinnamic acids. These acids have been revealed to enhance the efficiency of prototype medicinals (Nodiff et al., 1971). The derivatives of these acids have been used as precursors in the shikimic acid metabolic pathways of higher plants (Forgo et al., 2005). In an extension of such studies, in order to observe the effect of different substituents for improvement of the efficacy of these drugs, we have synthesized derivitives of these compounds and report the structure of compound (I). In the molecular structure of Compound (I), the central C8—C9 bond length of acrylate moiety proves a clear double bond character, and bonds C1—C8 and C9—C11 single bond character, which confirms localized bonding. In all the bond lengths and bond angles, a comparable behavior is observed as found in (Allen et al., 1987), 3-(6-nitro-1, 3-benzodioxol-5-yl)-2-phenylacrylic acid, (II) (Hussain et al., 2006). In the crystal structure of (I), Centro symmetric dimers are formed via O—H···O hydrogen bonds linking carboxylic acid groups. This arrangement is like that observed in the crystal structure of (II). In compound (I), these dimers are further connected by small links which form a slab like structure of the compound.

Related literature top

For related literature, see: Allen et al. (1987); Forgo et al. (2005); Hussain et al. (2006); Nodiff et al. (1971).

Experimental top

Compound (I) was synthesized as essayed in (Nodiff et al., 1971). A mixture of 2-Methyl benzaldehyde (6.6 mmol), (4-bromophenyl) acetic acid (6.6 mmol), potassium carbonate (15.4 mmol) and acetic anhydride (15.4 mmol) was slowly heated to 358 K and continued at that temperature for 24 h. To this hot solution, 10.0 ml distilled water and 5.0 ml 10% HCl were added sequentially. The solution was stirred for a further 2 h and after that filtered. Impurities were removed from the precipitated product by washing with water. Recrystallization was carried out in chloroform. (yield; 80%, m.p. 163–168 C.

Refinement top

The molecules form hydrogen-bonded dimers across inversion centres. The O1—O2 distance is 2.617 (4) Å.

Structure description top

Cinnamic Acid derived antibacterial drugs have increased the importance of these acids, especially halogenated Cinnamic acids. These acids have been revealed to enhance the efficiency of prototype medicinals (Nodiff et al., 1971). The derivatives of these acids have been used as precursors in the shikimic acid metabolic pathways of higher plants (Forgo et al., 2005). In an extension of such studies, in order to observe the effect of different substituents for improvement of the efficacy of these drugs, we have synthesized derivitives of these compounds and report the structure of compound (I). In the molecular structure of Compound (I), the central C8—C9 bond length of acrylate moiety proves a clear double bond character, and bonds C1—C8 and C9—C11 single bond character, which confirms localized bonding. In all the bond lengths and bond angles, a comparable behavior is observed as found in (Allen et al., 1987), 3-(6-nitro-1, 3-benzodioxol-5-yl)-2-phenylacrylic acid, (II) (Hussain et al., 2006). In the crystal structure of (I), Centro symmetric dimers are formed via O—H···O hydrogen bonds linking carboxylic acid groups. This arrangement is like that observed in the crystal structure of (II). In compound (I), these dimers are further connected by small links which form a slab like structure of the compound.

For related literature, see: Allen et al. (1987); Forgo et al. (2005); Hussain et al. (2006); Nodiff et al. (1971).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A thermal ellipsoid perspective drawing of the molecule, 50% probability.
[Figure 2] Fig. 2. Thermal ellipsoid perspective drawing showing the hydrogen-bonded dimer.
(E)-2-(4-Bromophenyl)-3-o-tolylacrylic acid top
Crystal data top
C16H13BrO2F(000) = 640
Mr = 317.17Dx = 1.505 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.0641 (12) ÅCell parameters from 4981 reflections
b = 15.208 (3) Åθ = 3.0–25.7°
c = 15.187 (3) ŵ = 2.93 mm1
β = 91.98 (3)°T = 298 K
V = 1399.7 (5) Å3Plate, colourless
Z = 40.72 × 0.48 × 0.12 mm
Data collection top
Rigaku Mercury CCD
diffractometer
2454 independent reflections
Radiation source: sealed tube2133 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
Detector resolution: 14.6199 pixels mm-1θmax = 25.0°, θmin = 3.0°
dtprofit.ref scansh = 77
Absorption correction: multi-scan
(REQAB; Rigaku/MSC, 1999)
k = 1814
Tmin = 0.222, Tmax = 0.706l = 1818
10277 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0375P)2 + 1.3644P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
2454 reflectionsΔρmax = 0.43 e Å3
175 parametersΔρmin = 0.40 e Å3
0 restraintsExtinction correction: SHELXTL (Bruker, 2000), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0086 (17)
Crystal data top
C16H13BrO2V = 1399.7 (5) Å3
Mr = 317.17Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.0641 (12) ŵ = 2.93 mm1
b = 15.208 (3) ÅT = 298 K
c = 15.187 (3) Å0.72 × 0.48 × 0.12 mm
β = 91.98 (3)°
Data collection top
Rigaku Mercury CCD
diffractometer
2454 independent reflections
Absorption correction: multi-scan
(REQAB; Rigaku/MSC, 1999)
2133 reflections with I > 2σ(I)
Tmin = 0.222, Tmax = 0.706Rint = 0.055
10277 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.11Δρmax = 0.43 e Å3
2454 reflectionsΔρmin = 0.40 e Å3
175 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
Br10.34229 (6)0.49805 (2)0.61545 (2)0.04791 (18)
O10.0639 (4)0.89770 (16)0.50704 (15)0.0498 (6)
O20.2513 (4)1.00144 (14)0.43676 (16)0.0423 (5)
H20.16301.03400.46170.051*
C10.6456 (5)0.8217 (2)0.30564 (17)0.0333 (6)
C20.8343 (5)0.8622 (2)0.27221 (19)0.0384 (7)
C30.9804 (5)0.8094 (3)0.2261 (2)0.0449 (8)
H31.11390.83510.20560.054*
C40.9393 (6)0.7225 (3)0.2094 (2)0.0495 (9)
H41.04150.68850.17660.059*
C50.7502 (6)0.6839 (2)0.2397 (2)0.0467 (8)
H50.71890.62320.22710.056*
C60.6057 (5)0.7333 (2)0.2884 (2)0.0408 (7)
H60.47620.70590.31060.049*
C70.8753 (6)0.9589 (3)0.2828 (2)0.0510 (9)
H7A1.02600.97180.27010.076*
H7B0.84730.97610.34220.076*
H7C0.77900.99090.24280.076*
C80.4923 (5)0.8763 (2)0.35516 (18)0.0343 (7)
H80.48260.93690.33760.041*
C90.3640 (4)0.8527 (2)0.42163 (18)0.0325 (6)
C100.2132 (5)0.9190 (2)0.45829 (19)0.0371 (7)
C110.3587 (5)0.7651 (2)0.46472 (17)0.0321 (6)
C12'0.5391 (5)0.7379 (2)0.51683 (18)0.0352 (7)
H12'0.66780.77460.52180.042*
C120.1737 (5)0.7111 (2)0.45780 (19)0.0371 (7)
H120.04820.72940.42210.045*
C13'0.5357 (5)0.6588 (2)0.56153 (19)0.0397 (7)
H13'0.66090.64040.59730.048*
C130.1680 (5)0.6314 (2)0.5017 (2)0.0398 (7)
H130.04080.59400.49610.048*
C140.3499 (5)0.6066 (2)0.55412 (18)0.0362 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0670 (3)0.0365 (2)0.0413 (2)0.00595 (16)0.01678 (16)0.00548 (14)
O10.0596 (15)0.0398 (14)0.0518 (14)0.0139 (11)0.0273 (11)0.0084 (11)
O20.0446 (12)0.0343 (12)0.0493 (13)0.0058 (10)0.0193 (10)0.0007 (10)
C10.0336 (15)0.0408 (17)0.0258 (13)0.0039 (13)0.0046 (11)0.0038 (12)
C20.0329 (15)0.052 (2)0.0303 (15)0.0013 (14)0.0023 (11)0.0037 (14)
C30.0361 (16)0.065 (2)0.0344 (16)0.0060 (15)0.0106 (13)0.0085 (16)
C40.051 (2)0.065 (3)0.0337 (16)0.0210 (18)0.0112 (14)0.0043 (16)
C50.066 (2)0.0388 (19)0.0359 (16)0.0105 (16)0.0116 (15)0.0028 (14)
C60.0455 (17)0.0439 (19)0.0338 (15)0.0043 (14)0.0124 (13)0.0040 (14)
C70.0441 (19)0.060 (2)0.0496 (19)0.0080 (17)0.0098 (15)0.0006 (18)
C80.0363 (15)0.0363 (17)0.0306 (14)0.0026 (13)0.0047 (11)0.0010 (13)
C90.0313 (14)0.0366 (16)0.0297 (14)0.0011 (12)0.0040 (11)0.0023 (12)
C100.0375 (15)0.0411 (19)0.0332 (15)0.0067 (13)0.0086 (12)0.0008 (13)
C110.0339 (14)0.0372 (17)0.0256 (13)0.0035 (12)0.0084 (11)0.0021 (12)
C12'0.0350 (15)0.0399 (18)0.0309 (14)0.0007 (13)0.0047 (11)0.0021 (13)
C120.0302 (15)0.0437 (19)0.0377 (16)0.0036 (13)0.0040 (12)0.0004 (14)
C13'0.0461 (18)0.0446 (19)0.0281 (14)0.0048 (14)0.0016 (12)0.0018 (13)
C130.0335 (15)0.0417 (18)0.0448 (17)0.0037 (13)0.0103 (12)0.0014 (15)
C140.0458 (17)0.0364 (17)0.0272 (14)0.0047 (13)0.0126 (12)0.0002 (12)
Geometric parameters (Å, º) top
Br1—C141.896 (3)C7—H7B0.9599
O1—C101.233 (4)C7—H7C0.9599
O2—C101.318 (4)C8—C91.344 (4)
O2—H20.8299C8—H80.9600
C1—C61.390 (5)C9—C101.483 (4)
C1—C21.410 (4)C9—C111.485 (4)
C1—C81.472 (4)C11—C12'1.391 (4)
C2—C31.401 (5)C11—C121.391 (4)
C2—C71.499 (5)C12'—C13'1.381 (5)
C3—C41.367 (5)C12'—H12'0.9600
C3—H30.9600C12—C131.384 (5)
C4—C51.382 (5)C12—H120.9600
C4—H40.9600C13'—C141.380 (4)
C5—C61.387 (5)C13'—H13'0.9600
C5—H50.9600C13—C141.391 (4)
C6—H60.9600C13—H130.9600
C7—H7A0.9599
C10—O2—H2109.5C9—C8—H8115.7
C6—C1—C2119.6 (3)C1—C8—H8115.7
C6—C1—C8122.2 (3)C8—C9—C10118.7 (3)
C2—C1—C8118.2 (3)C8—C9—C11126.4 (3)
C3—C2—C1117.7 (3)C10—C9—C11114.9 (2)
C3—C2—C7120.7 (3)O1—C10—O2122.5 (3)
C1—C2—C7121.6 (3)O1—C10—C9121.4 (3)
C4—C3—C2122.2 (3)O2—C10—C9116.0 (3)
C4—C3—H3118.9C12'—C11—C12119.0 (3)
C2—C3—H3118.9C12'—C11—C9119.3 (3)
C3—C4—C5119.8 (3)C12—C11—C9121.7 (3)
C3—C4—H4120.1C13'—C12'—C11120.9 (3)
C5—C4—H4120.1C13'—C12'—H12'119.6
C4—C5—C6119.6 (3)C11—C12'—H12'119.6
C4—C5—H5120.2C13—C12—C11120.9 (3)
C6—C5—H5120.2C13—C12—H12119.5
C5—C6—C1121.0 (3)C11—C12—H12119.5
C5—C6—H6119.5C14—C13'—C12'119.2 (3)
C1—C6—H6119.5C14—C13'—H13'120.4
C2—C7—H7A109.5C12'—C13'—H13'120.4
C2—C7—H7B109.5C12—C13—C14118.8 (3)
H7A—C7—H7B109.5C12—C13—H13120.6
C2—C7—H7C109.5C14—C13—H13120.6
H7A—C7—H7C109.5C13'—C14—C13121.3 (3)
H7B—C7—H7C109.5C13'—C14—Br1119.7 (2)
C9—C8—C1128.7 (3)C13—C14—Br1119.0 (2)
C6—C1—C2—C33.1 (4)C8—C9—C10—O214.9 (4)
C8—C1—C2—C3179.2 (3)C11—C9—C10—O2164.3 (3)
C6—C1—C2—C7175.1 (3)C8—C9—C11—C12'69.4 (4)
C8—C1—C2—C72.6 (4)C10—C9—C11—C12'109.6 (3)
C1—C2—C3—C43.4 (4)C8—C9—C11—C12113.7 (3)
C7—C2—C3—C4174.8 (3)C10—C9—C11—C1267.3 (4)
C2—C3—C4—C51.2 (5)C12—C11—C12'—C13'0.3 (4)
C3—C4—C5—C61.3 (5)C9—C11—C12'—C13'176.7 (3)
C4—C5—C6—C11.5 (5)C12'—C11—C12—C130.1 (4)
C2—C1—C6—C50.8 (4)C9—C11—C12—C13177.0 (3)
C8—C1—C6—C5178.3 (3)C11—C12'—C13'—C140.1 (4)
C6—C1—C8—C933.4 (5)C11—C12—C13—C140.9 (4)
C2—C1—C8—C9149.0 (3)C12'—C13'—C14—C130.9 (4)
C1—C8—C9—C10176.8 (3)C12'—C13'—C14—Br1179.8 (2)
C1—C8—C9—C114.2 (5)C12—C13—C14—C13'1.3 (4)
C8—C9—C10—O1166.2 (3)C12—C13—C14—Br1179.4 (2)
C11—C9—C10—O114.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.831.802.617 (3)167
Symmetry code: (i) x, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC16H13BrO2
Mr317.17
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)6.0641 (12), 15.208 (3), 15.187 (3)
β (°) 91.98 (3)
V3)1399.7 (5)
Z4
Radiation typeMo Kα
µ (mm1)2.93
Crystal size (mm)0.72 × 0.48 × 0.12
Data collection
DiffractometerRigaku Mercury CCD
Absorption correctionMulti-scan
(REQAB; Rigaku/MSC, 1999)
Tmin, Tmax0.222, 0.706
No. of measured, independent and
observed [I > 2σ(I)] reflections
10277, 2454, 2133
Rint0.055
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.098, 1.11
No. of reflections2454
No. of parameters175
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.40

Computer programs: CrystalClear (Rigaku/MSC, 2001), CrystalClear, SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.831.8012.617 (3)167
Symmetry code: (i) x, y+2, z+1.
 

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