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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Jan 9;66(Pt 2):o316. doi: 10.1107/S160053680905538X

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

Jasmine P Vennila a, D John Thiruvadigal b, Helen P Kavitha c, B Gunasekaran d, V Manivannan e,*
PMCID: PMC2979767  PMID: 21579746

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 ▶); Fegade et al. (2009 ▶); Foroumadi et al. (2007 ▶); Hodnett & Dunn (1970 ▶); Hu & Zhou (2004 ▶); Jada et al. (2008 ▶); Samadhiya & Halve (2001 ▶); Singh & Dash (1988 ▶). For related structures, see: Cui et al. (2009 ▶); Sun et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).graphic file with name e-66-0o316-scheme1.jpg

Experimental

Crystal data

  • C13H10BrNO

  • M r = 276.13

  • Orthorhombic, Inline graphic

  • 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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

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

e-66-0o316-sup1.cif (15.6KB, cif)

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

e-66-0o316-Isup2.hkl (128.5KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1i 0.82 2.05 2.848 (3) 164
C5—H5⋯Cg1ii 0.93 2.89 3.374 (3) 114
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

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.

Fig. 1.

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

Crystal data

C13H10BrNO F(000) = 1104
Mr = 276.13 Dx = 1.626 Mg m−3
Orthorhombic, Pbca Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab Cell parameters from 2371 reflections
a = 12.7035 (4) Å θ = 2.4–23.7°
b = 10.3897 (3) Å µ = 3.62 mm−1
c = 17.0899 (6) Å T = 295 K
V = 2255.62 (12) Å3 Block, brown
Z = 8 0.20 × 0.16 × 0.15 mm
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Data collection

Bruker Kappa APEXII CCD diffractometer 2670 independent reflections
Radiation source: fine-focus sealed tube 1710 reflections with I > 2σ(I)
graphite Rint = 0.043
ω and φ scans θmax = 27.8°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −12→16
Tmin = 0.503, Tmax = 0.581 k = −12→13
13273 measured reflections l = −22→22
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Refinement

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)] = 0.035 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086 H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0358P)2 + 0.8359P] where P = (Fo2 + 2Fc2)/3
2670 reflections (Δ/σ)max = 0.001
146 parameters Δρmax = 0.49 e Å−3
0 restraints Δρmin = −0.39 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.16600 (18) 0.0270 (2) 0.54592 (14) 0.0371 (6)
C2 0.2620 (2) −0.0367 (3) 0.54384 (16) 0.0463 (7)
H2 0.2727 −0.1086 0.5753 0.056*
C3 0.34124 (19) 0.0056 (3) 0.49578 (18) 0.0520 (7)
H3 0.4054 −0.0374 0.4944 0.062*
C4 0.32501 (19) 0.1120 (3) 0.44968 (15) 0.0422 (6)
C5 0.2319 (2) 0.1769 (3) 0.45068 (16) 0.0463 (7)
H5 0.2220 0.2490 0.4192 0.056*
C6 0.1528 (2) 0.1340 (3) 0.49907 (16) 0.0449 (7)
H6 0.0891 0.1780 0.5002 0.054*
C7 0.07751 (18) −0.0183 (3) 0.59347 (15) 0.0383 (6)
H7 0.0158 0.0298 0.5927 0.046*
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 −0.0736 0.0189 0.7031 0.044*
C10 −0.16897 (17) −0.1120 (2) 0.75198 (14) 0.0368 (6)
H10 −0.2155 −0.0532 0.7740 0.044*
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 −0.4174 0.7355 0.049*
C13 −0.02907 (18) −0.2855 (2) 0.68836 (15) 0.0388 (6)
H13 0.0186 −0.3443 0.6677 0.047*
N1 0.07946 (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 −0.2324 0.8226 0.075*
Br1 0.43298 (2) 0.16639 (3) 0.38080 (2) 0.06483 (15)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0383 (13) 0.0383 (15) 0.0348 (14) −0.0034 (11) −0.0019 (11) −0.0038 (12)
C2 0.0458 (14) 0.0461 (16) 0.0471 (16) 0.0036 (12) 0.0056 (13) 0.0117 (14)
C3 0.0386 (14) 0.0573 (19) 0.0599 (19) 0.0045 (13) 0.0086 (14) 0.0115 (15)
C4 0.0427 (14) 0.0468 (16) 0.0371 (15) −0.0113 (12) 0.0046 (12) 0.0009 (13)
C5 0.0549 (16) 0.0432 (16) 0.0407 (16) −0.0024 (13) 0.0003 (13) 0.0081 (13)
C6 0.0406 (14) 0.0464 (17) 0.0476 (17) 0.0047 (11) 0.0009 (13) 0.0066 (13)
C7 0.0322 (13) 0.0420 (16) 0.0406 (14) 0.0007 (10) −0.0006 (11) −0.0023 (13)
C8 0.0268 (11) 0.0357 (14) 0.0349 (13) −0.0010 (10) −0.0028 (10) 0.0021 (11)
C9 0.0337 (12) 0.0305 (13) 0.0452 (16) −0.0010 (10) −0.0018 (11) 0.0006 (12)
C10 0.0332 (13) 0.0360 (15) 0.0411 (15) 0.0066 (10) −0.0012 (11) −0.0013 (12)
C11 0.0291 (12) 0.0387 (16) 0.0403 (15) 0.0004 (10) 0.0010 (11) 0.0041 (11)
C12 0.0361 (12) 0.0308 (14) 0.0566 (18) 0.0013 (11) 0.0019 (12) 0.0056 (13)
C13 0.0319 (12) 0.0364 (15) 0.0480 (16) 0.0076 (11) 0.0022 (11) 0.0021 (13)
N1 0.0314 (10) 0.0404 (12) 0.0384 (13) −0.0021 (8) 0.0016 (9) 0.0000 (10)
O1 0.0371 (10) 0.0431 (11) 0.0688 (14) 0.0020 (8) 0.0169 (9) 0.0058 (10)
Br1 0.0582 (2) 0.0736 (3) 0.0627 (2) −0.01461 (15) 0.01935 (16) 0.01033 (18)
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Geometric parameters (Å, °)

C1—C6 1.380 (4) C8—C13 1.383 (3)
C1—C2 1.388 (3) C8—C9 1.388 (3)
C1—C7 1.465 (3) C8—N1 1.423 (3)
C2—C3 1.371 (4) C9—C10 1.375 (3)
C2—H2 0.9300 C9—H9 0.9300
C3—C4 1.373 (4) C10—C11 1.383 (4)
C3—H3 0.9300 C10—H10 0.9300
C4—C5 1.362 (4) C11—O1 1.356 (3)
C4—Br1 1.894 (2) C11—C12 1.382 (3)
C5—C6 1.376 (4) C12—C13 1.383 (3)
C5—H5 0.9300 C12—H12 0.9300
C6—H6 0.9300 C13—H13 0.9300
C7—N1 1.264 (3) O1—H1 0.8200
C7—H7 0.9300
C6—C1—C2 118.4 (2) C13—C8—C9 118.6 (2)
C6—C1—C7 119.2 (2) C13—C8—N1 117.1 (2)
C2—C1—C7 122.4 (2) C9—C8—N1 124.3 (2)
C3—C2—C1 120.5 (3) C10—C9—C8 120.9 (2)
C3—C2—H2 119.8 C10—C9—H9 119.6
C1—C2—H2 119.8 C8—C9—H9 119.6
C2—C3—C4 119.4 (2) C9—C10—C11 120.2 (2)
C2—C3—H3 120.3 C9—C10—H10 119.9
C4—C3—H3 120.3 C11—C10—H10 119.9
C5—C4—C3 121.5 (2) O1—C11—C12 117.2 (2)
C5—C4—Br1 119.3 (2) O1—C11—C10 123.3 (2)
C3—C4—Br1 119.2 (2) C12—C11—C10 119.5 (2)
C4—C5—C6 118.7 (3) C11—C12—C13 120.0 (2)
C4—C5—H5 120.6 C11—C12—H12 120.0
C6—C5—H5 120.6 C13—C12—H12 120.0
C5—C6—C1 121.4 (2) C12—C13—C8 120.8 (2)
C5—C6—H6 119.3 C12—C13—H13 119.6
C1—C6—H6 119.3 C8—C13—H13 119.6
N1—C7—C1 124.4 (2) C7—N1—C8 119.4 (2)
N1—C7—H7 117.8 C11—O1—H1 109.5
C1—C7—H7 117.8
C6—C1—C2—C3 −0.5 (4) N1—C8—C9—C10 −177.8 (2)
C7—C1—C2—C3 177.0 (3) C8—C9—C10—C11 −1.0 (4)
C1—C2—C3—C4 0.1 (5) C9—C10—C11—O1 179.4 (2)
C2—C3—C4—C5 0.2 (5) C9—C10—C11—C12 0.8 (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—C13 0.3 (4)
Br1—C4—C5—C6 177.9 (2) C11—C12—C13—C8 −1.2 (4)
C4—C5—C6—C1 −0.2 (4) C9—C8—C13—C12 1.0 (4)
C2—C1—C6—C5 0.5 (4) N1—C8—C13—C12 179.1 (2)
C7—C1—C6—C5 −177.0 (3) C1—C7—N1—C8 −178.2 (2)
C6—C1—C7—N1 176.6 (3) C13—C8—N1—C7 147.6 (3)
C2—C1—C7—N1 −0.9 (4) C9—C8—N1—C7 −34.5 (4)
C13—C8—C9—C10 0.1 (4)
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Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.
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D—H···A D—H H···A D···A D—H···A
O1—H1···N1i 0.82 2.05 2.848 (3) 164
C5—H5···Cg1ii 0.93 2.89 3.374 (3) 114
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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

  1. 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.
  2. Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Cui, C., Meng, Q. & Wang, Y. (2009). Acta Cryst. E65, o2472. [DOI] [PMC free article] [PubMed]
  4. El Masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429–1438.
  5. Fegade, J. D., Rane, S. S., Chaudhari, R. Y. & Patil, V. R. (2009). Digest J. Nanomater. Biostruct.4, 145–154.
  6. 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. [DOI] [PubMed]
  7. Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem.13, 768–770. [DOI] [PubMed]
  8. Hu, W. & Zhou, W. (2004). Bioorg. Med. Chem. Lett 14, 621–622. [DOI] [PubMed]
  9. 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. [DOI] [PMC free article] [PubMed]
  10. Samadhiya, S. & Halve, A. (2001). Orient J. Chem 17, 119–122.
  11. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  12. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  13. Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33–37.
  14. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-66-0o316-sup1.cif (15.6KB, cif)

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

e-66-0o316-Isup2.hkl (128.5KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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