2-[(3-Bromo­phen­yl)imino­meth­yl]phenol

Ren, X.-Y.; Jian, F.-F.

doi:10.1107/S1600536808027360

organic compounds

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2-[(3-Bromophenyl)iminomethyl]phenol

Xiao-Yan Ren ^a and Fang-Fang Jian ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 4 August 2008; accepted 25 August 2008; online 30 August 2008)

The title compound, C₁₃H₁₀BrNO, was prepared by reaction of 3-bromoaniline with 2-hydroxybenzaldehyde at 377 K. The molecular structure and packing are stabilized by an intramolecular O—H⋯N hydrogen-bond interaction.

CCDC reference: 702591

Related literature

For related literature, see: Jian et al. (2006 ); Rozwadowski et al. (1999 ).

Experimental

Crystal data

C₁₃H₁₀BrNO
M_r = 276.13
Monoclinic, P 2₁
a = 3.9700 (8) Å
b = 10.540 (2) Å
c = 13.200 (3) Å
β = 98.00 (3)°
V = 546.96 (19) Å³
Z = 2
Mo Kα radiation
μ = 3.73 mm⁻¹
T = 293 (2) K
0.12 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
2736 measured reflections
1822 independent reflections
1666 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.229
S = 1.13
1822 reflections
145 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.43 e Å⁻³
Δρ_min = −1.17 e Å⁻³
Absolute structure: Flack (1983 ), 787 Freidel pairs
Flack parameter: 0.1 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.599 (17)	149

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 702591

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536808027360/at2611sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536808027360/at2611Isup2.hkl

checkCIF report

Comment top

The recent growing interest in Schiff bases is also due to their ability to form intramolecular hydrogen bonds by electron coupling between acid–base centers (Rozwadowski et al., 1999). The part of our research is to find Schiff base with higher biological activity, we synthesized the title compound (I) and report its crystal structure here.

In the crystal structure of compound (I) (Fig. 1), the dihedral angle between the benzene rings (C1–C6) and (C7–C12) was 4.6 (2)°. The C═N bond length [1.273 (1) Å] is in agreement with that observed before (Jian et al., 2006). There are intramolecular O—H···N hydrogen-bond interactions to stabilize the crystal structure (Table 1, Fig. 2).

Related literature top

For related literature, see: Jian et al. (2006); Rozwadowski et al. (1999).

Experimental top

A mixture of 2-nitrobenzaldehyde (0.02 mol) and 4-methoxyaniline (0.02 mol) was stirred with ethanol (50 mL) at 377 K for 5 h, affording the title compound (4.33 g, yield 84.5%). Single crystals suitable for X-ray measurements were obtained by recrystallization from acetone at room temperature.

Structure description top

For related literature, see: Jian et al. (2006); Rozwadowski et al. (1999).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the packing and the intramolecular hydrogen bonding (dashed lines) of (I) in the unitcell.

2-[(3-Bromophenyl)iminomethyl]phenol top

Crystal data top

C₁₃H₁₀BrNO	F(000) = 276.0
M_r = 276.13	D_x = 1.676 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1666 reflections
a = 3.9700 (8) Å	θ = 1.6–25.0°
b = 10.540 (2) Å	µ = 3.73 mm⁻¹
c = 13.200 (3) Å	T = 293 K
β = 98.00 (3)°	Bar, yellow
V = 546.96 (19) Å³	0.12 × 0.10 × 0.07 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1666 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.0°, θ_min = 1.6°
φ and ω scans	h = −4→4
2736 measured reflections	k = −12→12
1822 independent reflections	l = −12→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.082	H-atom parameters constrained
wR(F²) = 0.229	w = 1/[σ²(F_o²) + (0.1154P)² + 2.8393P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
1822 reflections	Δρ_max = 1.43 e Å⁻³
145 parameters	Δρ_min = −1.17 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 787 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (4)

Crystal data top

C₁₃H₁₀BrNO	V = 546.96 (19) Å³
M_r = 276.13	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 3.9700 (8) Å	µ = 3.73 mm⁻¹
b = 10.540 (2) Å	T = 293 K
c = 13.200 (3) Å	0.12 × 0.10 × 0.07 mm
β = 98.00 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1666 reflections with I > 2σ(I)
2736 measured reflections	R_int = 0.032
1822 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	H-atom parameters constrained
wR(F²) = 0.229	Δρ_max = 1.43 e Å⁻³
S = 1.13	Δρ_min = −1.17 e Å⁻³
1822 reflections	Absolute structure: Flack (1983), 787 Freidel pairs
145 parameters	Absolute structure parameter: 0.1 (4)
1 restraint

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

	x	y	z	U_iso*/U_eq
Br1	0.4943 (3)	0.6144 (2)	0.53030 (8)	0.0544 (5)
N1	0.643 (3)	0.4449 (9)	0.9014 (8)	0.041 (2)
C4	0.538 (4)	0.5109 (12)	0.7289 (10)	0.046 (3)
H4A	0.6652	0.5830	0.7485	0.055*
C10	0.793 (3)	0.3864 (10)	1.0766 (9)	0.036 (3)
C3	0.402 (4)	0.4950 (13)	0.6277 (11)	0.049 (3)
C11	0.800 (4)	0.2937 (12)	1.1480 (10)	0.043 (3)
H11A	0.7186	0.2137	1.1274	0.052*
C5	0.487 (3)	0.4229 (12)	0.8000 (10)	0.043 (3)
C8	1.128 (4)	0.5145 (14)	1.2004 (12)	0.057 (4)
H8A	1.2470	0.5889	1.2187	0.068*
C12	0.918 (4)	0.3124 (13)	1.2476 (10)	0.052 (4)
H12A	0.8763	0.2550	1.2978	0.062*
C13	0.644 (4)	0.3630 (11)	0.9723 (11)	0.041 (3)
H13A	0.5431	0.2846	0.9561	0.050*
C9	0.978 (4)	0.4994 (12)	1.1041 (10)	0.045 (3)
C7	1.110 (4)	0.4238 (15)	1.2716 (13)	0.060 (4)
H7A	1.2254	0.4348	1.3373	0.072*
O1	0.995 (3)	0.5906 (16)	1.0355 (8)	0.081 (6)
H1	0.8925	0.5681	0.9801	0.121*
C6	0.304 (3)	0.3157 (12)	0.7675 (13)	0.050 (4)
H6A	0.2798	0.2530	0.8157	0.060*
C2	0.216 (4)	0.3883 (13)	0.5982 (12)	0.049 (3)
H2A	0.1275	0.3769	0.5298	0.059*
C1	0.157 (5)	0.2960 (13)	0.6708 (11)	0.054 (4)
H1B	0.0231	0.2250	0.6527	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0649 (8)	0.0635 (8)	0.0338 (6)	−0.0095 (9)	0.0028 (5)	0.0168 (7)
N1	0.053 (6)	0.034 (5)	0.034 (5)	−0.002 (4)	0.001 (5)	−0.001 (4)
C4	0.060 (8)	0.041 (7)	0.035 (7)	0.005 (6)	−0.002 (6)	0.001 (5)
C10	0.042 (7)	0.035 (6)	0.026 (6)	0.004 (5)	−0.009 (5)	−0.007 (5)
C3	0.053 (8)	0.053 (8)	0.040 (7)	0.006 (6)	0.000 (6)	−0.002 (6)
C11	0.052 (8)	0.045 (7)	0.035 (7)	0.015 (6)	0.009 (6)	0.002 (6)
C5	0.039 (7)	0.049 (7)	0.038 (7)	0.013 (6)	−0.002 (5)	−0.002 (5)
C8	0.061 (9)	0.043 (7)	0.060 (9)	−0.009 (6)	−0.015 (7)	−0.003 (6)
C12	0.073 (10)	0.045 (7)	0.034 (7)	0.001 (7)	−0.007 (6)	0.013 (6)
C13	0.060 (8)	0.028 (6)	0.034 (7)	0.004 (5)	0.000 (6)	0.000 (4)
C9	0.056 (8)	0.039 (6)	0.041 (7)	0.007 (6)	0.003 (6)	0.003 (6)
C7	0.052 (9)	0.066 (9)	0.060 (9)	0.002 (7)	−0.001 (7)	−0.005 (7)
O1	0.096 (8)	0.077 (16)	0.065 (7)	−0.043 (8)	−0.005 (6)	−0.004 (7)
C6	0.035 (7)	0.032 (6)	0.079 (10)	−0.009 (5)	−0.002 (7)	0.004 (6)
C2	0.039 (7)	0.059 (9)	0.049 (8)	0.003 (6)	0.006 (6)	−0.010 (7)
C1	0.084 (11)	0.043 (8)	0.037 (7)	−0.011 (7)	0.014 (7)	−0.013 (6)

Geometric parameters (Å, º) top

Br1—C3	1.872 (15)	C8—C7	1.35 (2)
N1—C13	1.273 (17)	C8—H8A	0.9300
N1—C5	1.414 (16)	C12—C7	1.41 (2)
C4—C5	1.354 (19)	C12—H12A	0.9300
C4—C3	1.379 (19)	C13—H13A	0.9300
C4—H4A	0.9300	C9—O1	1.328 (19)
C10—C11	1.355 (18)	C7—H7A	0.9300
C10—C9	1.420 (18)	O1—H1	0.8200
C10—C13	1.443 (18)	C6—C1	1.34 (2)
C3—C2	1.37 (2)	C6—H6A	0.9300
C11—C12	1.348 (19)	C2—C1	1.41 (2)
C11—H11A	0.9300	C2—H2A	0.9300
C5—C6	1.381 (18)	C1—H1B	0.9300
C8—C9	1.34 (2)

C13—N1—C5	122.7 (11)	C7—C12—H12A	121.8
C5—C4—C3	120.8 (13)	N1—C13—C10	123.0 (11)
C5—C4—H4A	119.6	N1—C13—H13A	118.5
C3—C4—H4A	119.6	C10—C13—H13A	118.5
C11—C10—C9	117.9 (11)	O1—C9—C8	120.3 (13)
C11—C10—C13	120.4 (11)	O1—C9—C10	120.4 (11)
C9—C10—C13	121.1 (11)	C8—C9—C10	119.3 (12)
C2—C3—C4	119.8 (14)	C8—C7—C12	120.8 (14)
C2—C3—Br1	120.4 (11)	C8—C7—H7A	119.6
C4—C3—Br1	119.7 (11)	C12—C7—H7A	119.6
C12—C11—C10	122.9 (13)	C9—O1—H1	109.5
C12—C11—H11A	118.6	C1—C6—C5	124.1 (13)
C10—C11—H11A	118.6	C1—C6—H6A	117.9
C4—C5—C6	117.9 (13)	C5—C6—H6A	117.9
C4—C5—N1	117.2 (12)	C3—C2—C1	120.5 (14)
C6—C5—N1	124.8 (13)	C3—C2—H2A	119.8
C9—C8—C7	121.2 (14)	C1—C2—H2A	119.8
C9—C8—H8A	119.4	C6—C1—C2	116.7 (13)
C7—C8—H8A	119.4	C6—C1—H1B	121.6
C11—C12—C7	116.5 (14)	C2—C1—H1B	121.6
C11—C12—H12A	121.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.599 (17)	149

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀BrNO
M_r	276.13
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	3.9700 (8), 10.540 (2), 13.200 (3)
β (°)	98.00 (3)
V (Å³)	546.96 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.73
Crystal size (mm)	0.12 × 0.10 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2736, 1822, 1666
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.229, 1.13
No. of reflections	1822
No. of parameters	145
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.43, −1.17
Absolute structure	Flack (1983), 787 Freidel pairs
Absolute structure parameter	0.1 (4)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.599 (17)	149

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jian, F.-F., Zhuang, R.-R., Wang, K.-F., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o3198–o3199. Web of Science CrossRef IUCr Journals Google Scholar
Rozwadowski, Z., Majewski, E., Dziembowska, T. & Hansen, P. E. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 2809–2817. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1863

https://doi.org/10.1107/S1600536808027360

Open

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