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ISSN: 2056-9890

2-[(3-Bromo­phen­yl)imino­meth­yl]phenol

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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.

Related literature

For related literature, see: Jian et al. (2006[Jian, F.-F., Zhuang, R.-R., Wang, K.-F., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o3198-o3199.]); Rozwadowski et al. (1999[Rozwadowski, Z., Majewski, E., Dziembowska, T. & Hansen, P. E. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 2809-2817.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10BrNO

  • Mr = 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)

  • Rint = 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

  • Δρmax = 1.43 e Å−3

  • Δρmin = −1.17 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 787 Freidel pairs

  • Flack parameter: 0.1 (4)

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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 CN 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.

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms, with O—H and C—H distances of 0.82 and 0.93 Å, respectively, and with Uiso(H) = 1.2 or 1.5Ueq of the parent atoms.

Structure description 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 CN 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).

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
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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
C13H10BrNOF(000) = 276.0
Mr = 276.13Dx = 1.676 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1666 reflections
a = 3.9700 (8) Åθ = 1.6–25.0°
b = 10.540 (2) ŵ = 3.73 mm1
c = 13.200 (3) ÅT = 293 K
β = 98.00 (3)°Bar, yellow
V = 546.96 (19) Å30.12 × 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 tubeRint = 0.032
Graphite monochromatorθmax = 25.0°, θmin = 1.6°
φ and ω scansh = 44
2736 measured reflectionsk = 1212
1822 independent reflectionsl = 1215
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)] = 0.082H-atom parameters constrained
wR(F2) = 0.229 w = 1/[σ2(Fo2) + (0.1154P)2 + 2.8393P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
1822 reflectionsΔρmax = 1.43 e Å3
145 parametersΔρmin = 1.17 e Å3
1 restraintAbsolute structure: Flack (1983), 787 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (4)
Crystal data top
C13H10BrNOV = 546.96 (19) Å3
Mr = 276.13Z = 2
Monoclinic, P21Mo Kα radiation
a = 3.9700 (8) ŵ = 3.73 mm1
b = 10.540 (2) ÅT = 293 K
c = 13.200 (3) Å0.12 × 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 reflectionsRint = 0.032
1822 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.082H-atom parameters constrained
wR(F2) = 0.229Δρmax = 1.43 e Å3
S = 1.13Δρmin = 1.17 e Å3
1822 reflectionsAbsolute structure: Flack (1983), 787 Freidel pairs
145 parametersAbsolute 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
xyzUiso*/Ueq
Br10.4943 (3)0.6144 (2)0.53030 (8)0.0544 (5)
N10.643 (3)0.4449 (9)0.9014 (8)0.041 (2)
C40.538 (4)0.5109 (12)0.7289 (10)0.046 (3)
H4A0.66520.58300.74850.055*
C100.793 (3)0.3864 (10)1.0766 (9)0.036 (3)
C30.402 (4)0.4950 (13)0.6277 (11)0.049 (3)
C110.800 (4)0.2937 (12)1.1480 (10)0.043 (3)
H11A0.71860.21371.12740.052*
C50.487 (3)0.4229 (12)0.8000 (10)0.043 (3)
C81.128 (4)0.5145 (14)1.2004 (12)0.057 (4)
H8A1.24700.58891.21870.068*
C120.918 (4)0.3124 (13)1.2476 (10)0.052 (4)
H12A0.87630.25501.29780.062*
C130.644 (4)0.3630 (11)0.9723 (11)0.041 (3)
H13A0.54310.28460.95610.050*
C90.978 (4)0.4994 (12)1.1041 (10)0.045 (3)
C71.110 (4)0.4238 (15)1.2716 (13)0.060 (4)
H7A1.22540.43481.33730.072*
O10.995 (3)0.5906 (16)1.0355 (8)0.081 (6)
H10.89250.56810.98010.121*
C60.304 (3)0.3157 (12)0.7675 (13)0.050 (4)
H6A0.27980.25300.81570.060*
C20.216 (4)0.3883 (13)0.5982 (12)0.049 (3)
H2A0.12750.37690.52980.059*
C10.157 (5)0.2960 (13)0.6708 (11)0.054 (4)
H1B0.02310.22500.65270.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0649 (8)0.0635 (8)0.0338 (6)0.0095 (9)0.0028 (5)0.0168 (7)
N10.053 (6)0.034 (5)0.034 (5)0.002 (4)0.001 (5)0.001 (4)
C40.060 (8)0.041 (7)0.035 (7)0.005 (6)0.002 (6)0.001 (5)
C100.042 (7)0.035 (6)0.026 (6)0.004 (5)0.009 (5)0.007 (5)
C30.053 (8)0.053 (8)0.040 (7)0.006 (6)0.000 (6)0.002 (6)
C110.052 (8)0.045 (7)0.035 (7)0.015 (6)0.009 (6)0.002 (6)
C50.039 (7)0.049 (7)0.038 (7)0.013 (6)0.002 (5)0.002 (5)
C80.061 (9)0.043 (7)0.060 (9)0.009 (6)0.015 (7)0.003 (6)
C120.073 (10)0.045 (7)0.034 (7)0.001 (7)0.007 (6)0.013 (6)
C130.060 (8)0.028 (6)0.034 (7)0.004 (5)0.000 (6)0.000 (4)
C90.056 (8)0.039 (6)0.041 (7)0.007 (6)0.003 (6)0.003 (6)
C70.052 (9)0.066 (9)0.060 (9)0.002 (7)0.001 (7)0.005 (7)
O10.096 (8)0.077 (16)0.065 (7)0.043 (8)0.005 (6)0.004 (7)
C60.035 (7)0.032 (6)0.079 (10)0.009 (5)0.002 (7)0.004 (6)
C20.039 (7)0.059 (9)0.049 (8)0.003 (6)0.006 (6)0.010 (7)
C10.084 (11)0.043 (8)0.037 (7)0.011 (7)0.014 (7)0.013 (6)
Geometric parameters (Å, º) top
Br1—C31.872 (15)C8—C71.35 (2)
N1—C131.273 (17)C8—H8A0.9300
N1—C51.414 (16)C12—C71.41 (2)
C4—C51.354 (19)C12—H12A0.9300
C4—C31.379 (19)C13—H13A0.9300
C4—H4A0.9300C9—O11.328 (19)
C10—C111.355 (18)C7—H7A0.9300
C10—C91.420 (18)O1—H10.8200
C10—C131.443 (18)C6—C11.34 (2)
C3—C21.37 (2)C6—H6A0.9300
C11—C121.348 (19)C2—C11.41 (2)
C11—H11A0.9300C2—H2A0.9300
C5—C61.381 (18)C1—H1B0.9300
C8—C91.34 (2)
C13—N1—C5122.7 (11)C7—C12—H12A121.8
C5—C4—C3120.8 (13)N1—C13—C10123.0 (11)
C5—C4—H4A119.6N1—C13—H13A118.5
C3—C4—H4A119.6C10—C13—H13A118.5
C11—C10—C9117.9 (11)O1—C9—C8120.3 (13)
C11—C10—C13120.4 (11)O1—C9—C10120.4 (11)
C9—C10—C13121.1 (11)C8—C9—C10119.3 (12)
C2—C3—C4119.8 (14)C8—C7—C12120.8 (14)
C2—C3—Br1120.4 (11)C8—C7—H7A119.6
C4—C3—Br1119.7 (11)C12—C7—H7A119.6
C12—C11—C10122.9 (13)C9—O1—H1109.5
C12—C11—H11A118.6C1—C6—C5124.1 (13)
C10—C11—H11A118.6C1—C6—H6A117.9
C4—C5—C6117.9 (13)C5—C6—H6A117.9
C4—C5—N1117.2 (12)C3—C2—C1120.5 (14)
C6—C5—N1124.8 (13)C3—C2—H2A119.8
C9—C8—C7121.2 (14)C1—C2—H2A119.8
C9—C8—H8A119.4C6—C1—C2116.7 (13)
C7—C8—H8A119.4C6—C1—H1B121.6
C11—C12—C7116.5 (14)C2—C1—H1B121.6
C11—C12—H12A121.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.599 (17)149

Experimental details

Crystal data
Chemical formulaC13H10BrNO
Mr276.13
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)3.9700 (8), 10.540 (2), 13.200 (3)
β (°) 98.00 (3)
V3)546.96 (19)
Z2
Radiation typeMo Kα
µ (mm1)3.73
Crystal size (mm)0.12 × 0.10 × 0.07
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2736, 1822, 1666
Rint0.032
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.082, 0.229, 1.13
No. of reflections1822
No. of parameters145
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.43, 1.17
Absolute structureFlack (1983), 787 Freidel pairs
Absolute structure parameter0.1 (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···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.599 (17)149
 

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationJian, 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
First citationRozwadowski, Z., Majewski, E., Dziembowska, T. & Hansen, P. E. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 2809–2817.  CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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