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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o316.
Published online 2010 January 9. doi:  10.1107/S160053680905538X
PMCID: PMC2979767

(E)-4-[(4-Bromo­benzyl­idene)amino]phenol

Abstract

In the title compound, C13H10BrNO, the dihedral angle between the benzene rings is 35.20 (8)°. In the crystal, mol­ecules are linked by O—H(...)N hydrogen bonds, forming a zigzag chain along the a axis. A weak C—H(...)π inter­action is observed between the chains.

Related literature

For the biological activity of benzyl­idene derivatives, see: El Masry et al. (2000 [triangle]); Fegade et al. (2009 [triangle]); Foroumadi et al. (2007 [triangle]); Hodnett & Dunn (1970 [triangle]); Hu & Zhou (2004 [triangle]); Jada et al. (2008 [triangle]); Samadhiya & Halve (2001 [triangle]); Singh & Dash (1988 [triangle]). For related structures, see: Cui et al. (2009 [triangle]); Sun et al. (2009 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o316-scheme1.jpg

Experimental

Crystal data

  • C13H10BrNO
  • M r = 276.13
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o316-efi1.jpg
  • a = 12.7035 (4) Å
  • b = 10.3897 (3) Å
  • c = 17.0899 (6) Å
  • V = 2255.62 (12) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.62 mm−1
  • T = 295 K
  • 0.20 × 0.16 × 0.15 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.503, T max = 0.581
  • 13273 measured reflections
  • 2670 independent reflections
  • 1710 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.086
  • S = 1.00
  • 2670 reflections
  • 146 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.40 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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905538X/is2508sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905538X/is2508Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.

supplementary crystallographic information

Comment

Benzylidene derivatives exhibit antitumor (Hu & Zhou 2004) and antioxidant (Foroumadi et al., 2007) activities. Some N-benzylidene aniline derivatives show biological activities sucs as antibacterial (El Masry et al., 2000), antifungal (Singh & Dash, 1988), anticancer (Hodnett & Dunn, 1970) and herbicidal (Samadhiya & Halve, 2001). In addition, benzylidene derivatives of andrographolide are potential anticancer agents (Jada et al., 2008) and some of the benzylidene derivatives are acting as selective cyclooxygenase-2-inhibitors (Fegade et al., 2009).

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Cui et al., 2009; Sun et al., 2009). The dihedral angle between the benzene rings is 35.20 (8)°. The C—Br bond distance is 1.894 (2) Å, which is comparable to the literature value of 1.883 (15) Å (Allen et al., 1987). The crystal packing is stabilized by an O—H···N hydrogen bond and a weak C—H···π interaction (Table 1).

Experimental

A mixture of 4-bromobenzaldehyde (5 mmol), 4-aminophenol (5 mmol) and ethanol (40 ml) was refluxed for 2 h. It was then allowed to cool and filtered. Recrystallization of the crude product from ethanol yielded brown colored crystals.

Refinement

H atoms were positioned geometrically and refined using riding model, with O—H = 0.82 Å and Uiso(H) = 1.2Ueq(O), and C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C13H10BrNOF(000) = 1104
Mr = 276.13Dx = 1.626 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2371 reflections
a = 12.7035 (4) Åθ = 2.4–23.7°
b = 10.3897 (3) ŵ = 3.62 mm1
c = 17.0899 (6) ÅT = 295 K
V = 2255.62 (12) Å3Block, brown
Z = 80.20 × 0.16 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer2670 independent reflections
Radiation source: fine-focus sealed tube1710 reflections with I > 2σ(I)
graphiteRint = 0.043
ω and [var phi] scansθmax = 27.8°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→16
Tmin = 0.503, Tmax = 0.581k = −12→13
13273 measured reflectionsl = −22→22

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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0358P)2 + 0.8359P] where P = (Fo2 + 2Fc2)/3
2670 reflections(Δ/σ)max = 0.001
146 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = −0.39 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.16600 (18)0.0270 (2)0.54592 (14)0.0371 (6)
C20.2620 (2)−0.0367 (3)0.54384 (16)0.0463 (7)
H20.2727−0.10860.57530.056*
C30.34124 (19)0.0056 (3)0.49578 (18)0.0520 (7)
H30.4054−0.03740.49440.062*
C40.32501 (19)0.1120 (3)0.44968 (15)0.0422 (6)
C50.2319 (2)0.1769 (3)0.45068 (16)0.0463 (7)
H50.22200.24900.41920.056*
C60.1528 (2)0.1340 (3)0.49907 (16)0.0449 (7)
H60.08910.17800.50020.054*
C70.07751 (18)−0.0183 (3)0.59347 (15)0.0383 (6)
H70.01580.02980.59270.046*
C8−0.01245 (17)−0.1551 (2)0.67752 (14)0.0325 (5)
C9−0.08369 (16)−0.0690 (2)0.70991 (15)0.0365 (6)
H9−0.07360.01890.70310.044*
C10−0.16897 (17)−0.1120 (2)0.75198 (14)0.0368 (6)
H10−0.2155−0.05320.77400.044*
C11−0.18585 (16)−0.2426 (2)0.76165 (15)0.0360 (6)
C12−0.11568 (19)−0.3294 (2)0.72949 (16)0.0412 (6)
H12−0.1267−0.41740.73550.049*
C13−0.02907 (18)−0.2855 (2)0.68836 (15)0.0388 (6)
H130.0186−0.34430.66770.047*
N10.07946 (14)−0.1183 (2)0.63553 (12)0.0367 (5)
O1−0.26777 (13)−0.29148 (18)0.80295 (12)0.0497 (5)
H1−0.3015−0.23240.82260.075*
Br10.43298 (2)0.16639 (3)0.38080 (2)0.06483 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0383 (13)0.0383 (15)0.0348 (14)−0.0034 (11)−0.0019 (11)−0.0038 (12)
C20.0458 (14)0.0461 (16)0.0471 (16)0.0036 (12)0.0056 (13)0.0117 (14)
C30.0386 (14)0.0573 (19)0.0599 (19)0.0045 (13)0.0086 (14)0.0115 (15)
C40.0427 (14)0.0468 (16)0.0371 (15)−0.0113 (12)0.0046 (12)0.0009 (13)
C50.0549 (16)0.0432 (16)0.0407 (16)−0.0024 (13)0.0003 (13)0.0081 (13)
C60.0406 (14)0.0464 (17)0.0476 (17)0.0047 (11)0.0009 (13)0.0066 (13)
C70.0322 (13)0.0420 (16)0.0406 (14)0.0007 (10)−0.0006 (11)−0.0023 (13)
C80.0268 (11)0.0357 (14)0.0349 (13)−0.0010 (10)−0.0028 (10)0.0021 (11)
C90.0337 (12)0.0305 (13)0.0452 (16)−0.0010 (10)−0.0018 (11)0.0006 (12)
C100.0332 (13)0.0360 (15)0.0411 (15)0.0066 (10)−0.0012 (11)−0.0013 (12)
C110.0291 (12)0.0387 (16)0.0403 (15)0.0004 (10)0.0010 (11)0.0041 (11)
C120.0361 (12)0.0308 (14)0.0566 (18)0.0013 (11)0.0019 (12)0.0056 (13)
C130.0319 (12)0.0364 (15)0.0480 (16)0.0076 (11)0.0022 (11)0.0021 (13)
N10.0314 (10)0.0404 (12)0.0384 (13)−0.0021 (8)0.0016 (9)0.0000 (10)
O10.0371 (10)0.0431 (11)0.0688 (14)0.0020 (8)0.0169 (9)0.0058 (10)
Br10.0582 (2)0.0736 (3)0.0627 (2)−0.01461 (15)0.01935 (16)0.01033 (18)

Geometric parameters (Å, °)

C1—C61.380 (4)C8—C131.383 (3)
C1—C21.388 (3)C8—C91.388 (3)
C1—C71.465 (3)C8—N11.423 (3)
C2—C31.371 (4)C9—C101.375 (3)
C2—H20.9300C9—H90.9300
C3—C41.373 (4)C10—C111.383 (4)
C3—H30.9300C10—H100.9300
C4—C51.362 (4)C11—O11.356 (3)
C4—Br11.894 (2)C11—C121.382 (3)
C5—C61.376 (4)C12—C131.383 (3)
C5—H50.9300C12—H120.9300
C6—H60.9300C13—H130.9300
C7—N11.264 (3)O1—H10.8200
C7—H70.9300
C6—C1—C2118.4 (2)C13—C8—C9118.6 (2)
C6—C1—C7119.2 (2)C13—C8—N1117.1 (2)
C2—C1—C7122.4 (2)C9—C8—N1124.3 (2)
C3—C2—C1120.5 (3)C10—C9—C8120.9 (2)
C3—C2—H2119.8C10—C9—H9119.6
C1—C2—H2119.8C8—C9—H9119.6
C2—C3—C4119.4 (2)C9—C10—C11120.2 (2)
C2—C3—H3120.3C9—C10—H10119.9
C4—C3—H3120.3C11—C10—H10119.9
C5—C4—C3121.5 (2)O1—C11—C12117.2 (2)
C5—C4—Br1119.3 (2)O1—C11—C10123.3 (2)
C3—C4—Br1119.2 (2)C12—C11—C10119.5 (2)
C4—C5—C6118.7 (3)C11—C12—C13120.0 (2)
C4—C5—H5120.6C11—C12—H12120.0
C6—C5—H5120.6C13—C12—H12120.0
C5—C6—C1121.4 (2)C12—C13—C8120.8 (2)
C5—C6—H6119.3C12—C13—H13119.6
C1—C6—H6119.3C8—C13—H13119.6
N1—C7—C1124.4 (2)C7—N1—C8119.4 (2)
N1—C7—H7117.8C11—O1—H1109.5
C1—C7—H7117.8
C6—C1—C2—C3−0.5 (4)N1—C8—C9—C10−177.8 (2)
C7—C1—C2—C3177.0 (3)C8—C9—C10—C11−1.0 (4)
C1—C2—C3—C40.1 (5)C9—C10—C11—O1179.4 (2)
C2—C3—C4—C50.2 (5)C9—C10—C11—C120.8 (4)
C2—C3—C4—Br1−177.9 (2)O1—C11—C12—C13−178.4 (2)
C3—C4—C5—C6−0.1 (4)C10—C11—C12—C130.3 (4)
Br1—C4—C5—C6177.9 (2)C11—C12—C13—C8−1.2 (4)
C4—C5—C6—C1−0.2 (4)C9—C8—C13—C121.0 (4)
C2—C1—C6—C50.5 (4)N1—C8—C13—C12179.1 (2)
C7—C1—C6—C5−177.0 (3)C1—C7—N1—C8−178.2 (2)
C6—C1—C7—N1176.6 (3)C13—C8—N1—C7147.6 (3)
C2—C1—C7—N1−0.9 (4)C9—C8—N1—C7−34.5 (4)
C13—C8—C9—C100.1 (4)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.822.052.848 (3)164
C5—H5···Cg1ii0.932.893.374 (3)114

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2508).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cui, C., Meng, Q. & Wang, Y. (2009). Acta Cryst. E65, o2472. [PMC free article] [PubMed]
  • El Masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429–1438.
  • Fegade, J. D., Rane, S. S., Chaudhari, R. Y. & Patil, V. R. (2009). Digest J. Nanomater. Biostruct.4, 145–154.
  • Foroumadi, A., Samzadeh Kermani, A., Emami, S., Dehghan, G., Sorkhi, M., Arabsorkhi, F., Heidari, M. R., Abdollahi, M. & Shafiee, A. (2007). Bioorg. Med. Chem. Lett 17, 6764–6769. [PubMed]
  • Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem.13, 768–770. [PubMed]
  • Hu, W. & Zhou, W. (2004). Bioorg. Med. Chem. Lett 14, 621–622. [PubMed]
  • Jada, S. R., Matthews, C., Saad, M. S., Hamzah, A. S., Lajis, N. H., Stevens, M. F. G. & Stanslas, J. (2008). Br. J. Pharmacol 155, 641–654. [PMC free article] [PubMed]
  • Samadhiya, S. & Halve, A. (2001). Orient J. Chem 17, 119–122.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33–37.
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Sun, Y., Fu, S., Zhang, J., Wang, X. & Wang, D. (2009). Acta Cryst. E65, o237. [PMC free article] [PubMed]

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