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

Vennila, J.P.; Thiruvadigal, D.J.; Kavitha, H.P.; Gunasekaran, B.; Manivannan, V.

doi:10.1107/S160053680905538X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o316

https://doi.org/10.1107/S160053680905538X

Open

access

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

Jasmine P. Vennila,^a D. John Thiruvadigal,^b Helen P. Kavitha,^c B. Gunasekaran ^d and V. Manivannan ^e ^*

^aDepartment of Physics, Panimalar Institute of Technology, Chennai 602 103, India, ^bDepartment of Physics, SRM University, Kattankulathur Campus, Chennai, India, ^cDepartment of Chemistry, SRM University, Ramapuram Campus, Chennai 600 089, India, ^dDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 22 December 2009; accepted 24 December 2009; online 9 January 2010)

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 ).

Experimental

Crystal data

C₁₃H₁₀BrNO
M_r = 276.13
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.086
S = 1.00
2670 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) -x, -y, -z+1.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680905538X/is2508Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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).

Experimental top

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.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

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

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

Crystal data top

C₁₃H₁₀BrNO	F(000) = 1104
M_r = 276.13	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	2670 independent reflections
Radiation source: fine-focus sealed tube	1710 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω and φ scans	θ_max = 27.8°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→16
T_min = 0.503, T_max = 0.581	k = −12→13
13273 measured reflections	l = −22→22

Refinement top

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(F_o²) + (0.0358P)² + 0.8359P] where P = (F_o² + 2F_c²)/3
2670 reflections	(Δ/σ)_max = 0.001
146 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₃H₁₀BrNO	V = 2255.62 (12) Å³
M_r = 276.13	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.7035 (4) Å	µ = 3.62 mm⁻¹
b = 10.3897 (3) Å	T = 295 K
c = 17.0899 (6) Å	0.20 × 0.16 × 0.15 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2670 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1710 reflections with I > 2σ(I)
T_min = 0.503, T_max = 0.581	R_int = 0.043
13273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.00	Δρ_max = 0.49 e Å⁻³
2670 reflections	Δρ_min = −0.40 e Å⁻³
146 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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀BrNO
M_r	276.13
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	12.7035 (4), 10.3897 (3), 17.0899 (6)
V (Å³)	2255.62 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.62
Crystal size (mm)	0.20 × 0.16 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.503, 0.581
No. of measured, independent and observed [I > 2σ(I)] reflections	13273, 2670, 1710
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.086, 1.00
No. of reflections	2670
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.40

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

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

Acknowledgements

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

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. CSD CrossRef Web of Science Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cui, C., Meng, Q. & Wang, Y. (2009). Acta Cryst. E65, o2472. Web of Science CSD CrossRef IUCr Journals Google Scholar
El Masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429–1438. Web of Science CrossRef CAS Google Scholar
Fegade, J. D., Rane, S. S., Chaudhari, R. Y. & Patil, V. R. (2009). Digest J. Nanomater. Biostruct. 4, 145–154. Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem. 13, 768–770. CrossRef CAS PubMed Web of Science Google Scholar
Hu, W. & Zhou, W. (2004). Bioorg. Med. Chem. Lett. 14, 621–622. Web of Science CrossRef PubMed CAS Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
Samadhiya, S. & Halve, A. (2001). Orient J. Chem. 17, 119–122. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33–37. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y., Fu, S., Zhang, J., Wang, X. & Wang, D. (2009). Acta Cryst. E65, o237. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o316

https://doi.org/10.1107/S160053680905538X

Open

access