(E)-2-[(5-Bromo-2-hydroxy­benzyl­idene)amino]benzonitrile

Zhou, J.-C.; Li, N.-X.; Zhang, C.-M.; Zhang, Z.-Y.

doi:10.1107/S1600536809027950

organic compounds

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Volume 65| Part 8| August 2009| Page o1949

doi:10.1107/S1600536809027950

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(E)-2-[(5-Bromo-2-hydroxybenzylidene)amino]benzonitrile

Jian-Cheng Zhou,^a ^* Nai-Xu Li,^a Chuan-Ming Zhang ^a and Zheng-Yun Zhang ^a

^aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: jczhou@seu.edu.cn

(Received 15 July 2009; accepted 16 July 2009; online 22 July 2009)

In the molecule of the title compound, C₁₄H₉BrN₂O, the dihedral angle between the aromatic rings is 1.09 (4)°. Intramolecular O—H⋯N hydrogen bonding results in the formation of a planar (r.m.s. deviation = 0.0140 Å) six-membered ring. In the crystal structure, intermolecular C—H⋯N interactions link the molecules into chains.

Related literature

For general background to Schiff base compounds in coordination chemistry, see: Chen et al. (2008 ); May et al. (2004 ); Weber et al. (2007 ). For a related structure, see: Elmalı et al. (1999 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₉BrN₂O
M_r = 301.14
Orthorhombic, P c a 2₁
a = 25.609 (8) Å
b = 3.9299 (12) Å
c = 12.368 (4) Å
V = 1244.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 3.29 mm⁻¹
T = 294 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.518, T_max = 0.518
9720 measured reflections
2771 independent reflections
1737 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.090
S = 1.01
2771 reflections
163 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1271 Friedel pairs
Flack parameter: 0.039 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.93	2.651 (4)	146
C7—H7A⋯N2ⁱ	0.93	2.44	3.326 (4)	160
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+1, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027950/hk2739sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027950/hk2739Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have received considerable attention for many years, primarily due to their importance in the development of coordination chemistry related to magnetism (Weber et al., 2007), catalysis (Chen et al., 2008) and biological process (May et al., 2004). We report herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable with the corresponding values in a similar compound (Elmalı et al., 1999). Rings A (C1-C6) and B (C8-C13) are, of course, planar, and they are oriented at a dihedral angle of A/B = 1.09 (4)°. Intramolecular O-H···N hydrogen bond (Table 1) results in the formation of planar six-membered ring C (O1/N1/C1/C2/C7/H1A), it is oriented with respect to rings A and B at dihedral angles of A/C = 2.00 (4) and B/C = 1.42 (4) °. So, rings A, B and C are almost coplanar.

In the crystal structure, intermolecular C-H···N interactions link the molecules into chains (Fig. 2), , in which they may be effective in the stabilization of the structure.

Related literature top

For general background to Schiff base compounds in coordination chemistry, see: Chen et al. (2008); May et al. (2004); Weber et al. (2007). For a related structure, see: Elmalı et al. (1999). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of hte title compound, 2-aminobenzonitrile (0.472 g, 4 mmol) and 5-bromo-2-hydroxybenzaldehyde (0.8 g, 4 mmol) were dissolved in ethanol (20 ml). The mixture was heated to reflux for 5 h, and then cooled to room temperature. The solution was filtered and after two weeks yellow crystals suitable for X-ray analysis were obtained.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

(E)-2-[(5-Bromo-2-hydroxybenzylidene)amino]benzonitrile top

Crystal data top

C₁₄H₉BrN₂O	F(000) = 600
M_r = 301.14	D_x = 1.607 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1688 reflections
a = 25.609 (8) Å	θ = 3.1–27.7°
b = 3.9299 (12) Å	µ = 3.29 mm⁻¹
c = 12.368 (4) Å	T = 294 K
V = 1244.7 (7) Å³	Prism, yellow
Z = 4	0.2 × 0.2 × 0.2 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2771 independent reflections
Radiation source: fine-focus sealed tube	1737 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.6°, θ_min = 1.6°
ϕ and ω scans	h = −33→33
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −5→5
T_min = 0.518, T_max = 0.518	l = −16→14
9720 measured reflections

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0283P)² + 0.0106P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2771 reflections	Δρ_max = 0.23 e Å⁻³
163 parameters	Δρ_min = −0.29 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1271 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.039 (14)

Crystal data top

C₁₄H₉BrN₂O	V = 1244.7 (7) Å³
M_r = 301.14	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 25.609 (8) Å	µ = 3.29 mm⁻¹
b = 3.9299 (12) Å	T = 294 K
c = 12.368 (4) Å	0.2 × 0.2 × 0.2 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2771 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1737 reflections with I > 2σ(I)
T_min = 0.518, T_max = 0.518	R_int = 0.048
9720 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.090	Δρ_max = 0.23 e Å⁻³
S = 1.01	Δρ_min = −0.29 e Å⁻³
2771 reflections	Absolute structure: Flack (1983), 1271 Friedel pairs
163 parameters	Absolute structure parameter: 0.039 (14)
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	0.014802 (15)	0.46800 (11)	0.49637 (9)	0.0816 (2)
O1	0.15855 (14)	−0.0121 (8)	0.1439 (2)	0.0767 (9)
H1A	0.1892	0.0184	0.1605	0.115*
N1	0.23690 (11)	0.1858 (9)	0.2691 (3)	0.0471 (7)
N2	0.28448 (17)	−0.1697 (11)	0.0417 (3)	0.0800 (12)
C1	0.14763 (14)	0.2551 (10)	0.3176 (3)	0.0481 (9)
C2	0.12781 (19)	0.1038 (11)	0.2221 (4)	0.0567 (12)
C3	0.0737 (2)	0.0789 (11)	0.2121 (4)	0.0723 (13)
H3A	0.0598	−0.0122	0.1490	0.087*
C4	0.04062 (17)	0.1828 (11)	0.2912 (4)	0.0679 (12)
H4A	0.0047	0.1582	0.2825	0.081*
C5	0.06036 (14)	0.3244 (10)	0.3842 (4)	0.0576 (10)
C6	0.11302 (15)	0.3625 (11)	0.3970 (3)	0.0543 (10)
H6A	0.1259	0.4619	0.4598	0.065*
C7	0.20246 (14)	0.2971 (10)	0.3346 (3)	0.0488 (9)
H7A	0.2135	0.4110	0.3964	0.059*
C8	0.29066 (13)	0.2276 (9)	0.2900 (3)	0.0458 (9)
C9	0.32433 (17)	0.1123 (10)	0.2105 (3)	0.0523 (10)
C10	0.37810 (18)	0.1385 (12)	0.2213 (4)	0.0622 (12)
H10A	0.4001	0.0623	0.1666	0.075*
C11	0.39839 (16)	0.2791 (13)	0.3143 (4)	0.0735 (13)
H11A	0.4344	0.2974	0.3227	0.088*
C12	0.36610 (17)	0.3907 (12)	0.3933 (4)	0.0661 (12)
H12A	0.3802	0.4864	0.4556	0.079*
C13	0.31227 (16)	0.3646 (12)	0.3830 (4)	0.0613 (11)
H13A	0.2907	0.4392	0.4386	0.074*
C14	0.30179 (18)	−0.0458 (12)	0.1155 (4)	0.0598 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0607 (2)	0.0846 (3)	0.0995 (4)	0.0101 (2)	0.0174 (3)	0.0112 (4)
O1	0.086 (2)	0.096 (3)	0.0480 (19)	−0.0127 (17)	−0.0052 (17)	−0.0184 (16)
N1	0.0530 (19)	0.054 (2)	0.0344 (18)	−0.0040 (14)	0.0005 (15)	−0.0044 (16)
N2	0.106 (3)	0.081 (3)	0.054 (3)	0.002 (2)	0.007 (2)	−0.024 (2)
C1	0.055 (2)	0.044 (2)	0.045 (2)	−0.0054 (19)	−0.005 (2)	0.0047 (19)
C2	0.073 (3)	0.050 (3)	0.047 (3)	−0.009 (2)	−0.004 (3)	−0.005 (2)
C3	0.075 (3)	0.076 (3)	0.067 (3)	−0.015 (3)	−0.024 (3)	0.004 (3)
C4	0.052 (2)	0.060 (3)	0.091 (4)	−0.010 (2)	−0.015 (3)	0.009 (3)
C5	0.049 (2)	0.048 (2)	0.076 (3)	0.0014 (18)	−0.001 (2)	0.016 (2)
C6	0.056 (2)	0.056 (3)	0.052 (3)	−0.0010 (19)	−0.003 (2)	−0.006 (2)
C7	0.059 (2)	0.049 (2)	0.038 (2)	−0.0061 (18)	−0.006 (2)	−0.002 (2)
C8	0.057 (2)	0.042 (2)	0.038 (2)	−0.0070 (17)	0.000 (2)	0.0003 (19)
C9	0.066 (3)	0.046 (2)	0.045 (3)	0.0001 (19)	0.005 (2)	0.004 (2)
C10	0.062 (3)	0.061 (3)	0.064 (3)	0.000 (2)	0.012 (3)	−0.003 (3)
C11	0.054 (2)	0.077 (3)	0.089 (4)	−0.003 (2)	0.010 (3)	0.000 (3)
C12	0.065 (3)	0.069 (3)	0.064 (3)	−0.009 (2)	−0.018 (2)	−0.008 (2)
C13	0.057 (2)	0.076 (3)	0.051 (3)	−0.006 (2)	0.001 (2)	−0.009 (2)
C14	0.076 (3)	0.059 (3)	0.045 (3)	0.005 (2)	0.014 (2)	−0.007 (2)

Geometric parameters (Å, º) top

Br1—C5	1.898 (4)	C7—C1	1.429 (5)
O1—C2	1.328 (6)	C7—H7A	0.9300
O1—H1A	0.8200	C8—C9	1.385 (5)
N1—C7	1.275 (4)	C8—C13	1.384 (5)
N1—C8	1.411 (4)	C9—C10	1.387 (6)
C2—C1	1.416 (6)	C10—C11	1.377 (6)
C3—C2	1.393 (7)	C10—H10A	0.9300
C3—C4	1.358 (7)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C11	1.354 (6)
C4—H4A	0.9300	C12—H12A	0.9300
C5—C4	1.374 (6)	C13—C12	1.388 (6)
C6—C1	1.388 (5)	C13—H13A	0.9300
C6—C5	1.366 (5)	C14—N2	1.125 (5)
C6—H6A	0.9300	C14—C9	1.449 (7)

C2—O1—H1A	109.5	N1—C7—H7A	118.5
C7—N1—C8	121.2 (3)	C1—C7—H7A	118.5
C2—C1—C7	121.6 (4)	C9—C8—N1	116.0 (3)
C6—C1—C2	119.2 (4)	C9—C8—C13	117.9 (3)
C6—C1—C7	119.2 (4)	C13—C8—N1	126.0 (3)
O1—C2—C1	122.6 (4)	C8—C9—C10	121.7 (4)
O1—C2—C3	120.0 (4)	C8—C9—C14	118.0 (4)
C3—C2—C1	117.4 (4)	C10—C9—C14	120.4 (4)
C2—C3—H3A	118.8	C9—C10—H10A	120.5
C4—C3—C2	122.4 (5)	C11—C10—C9	119.0 (4)
C4—C3—H3A	118.8	C11—C10—H10A	120.5
C3—C4—C5	119.7 (4)	C10—C11—H11A	119.9
C3—C4—H4A	120.2	C12—C11—C10	120.2 (4)
C5—C4—H4A	120.2	C12—C11—H11A	119.9
C4—C5—Br1	120.4 (3)	C11—C12—C13	121.0 (4)
C6—C5—Br1	119.3 (3)	C11—C12—H12A	119.5
C6—C5—C4	120.3 (4)	C13—C12—H12A	119.5
C1—C6—H6A	119.5	C8—C13—C12	120.2 (4)
C5—C6—C1	121.0 (4)	C8—C13—H13A	119.9
C5—C6—H6A	119.5	C12—C13—H13A	119.9
N1—C7—C1	123.1 (3)	N2—C14—C9	179.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.93	2.651 (4)	146
C7—H7A···N2ⁱ	0.93	2.44	3.326 (4)	160

Symmetry code: (i) −x+1/2, y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₉BrN₂O
M_r	301.14
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	294
a, b, c (Å)	25.609 (8), 3.9299 (12), 12.368 (4)
V (Å³)	1244.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.29
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.518, 0.518
No. of measured, independent and observed [I > 2σ(I)] reflections	9720, 2771, 1737
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.090, 1.01
No. of reflections	2771
No. of parameters	163
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.29
Absolute structure	Flack (1983), 1271 Friedel pairs
Absolute structure parameter	0.039 (14)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.93	2.651 (4)	146
C7—H7A···N2ⁱ	0.93	2.44	3.326 (4)	160

Symmetry code: (i) −x+1/2, y+1, z+1/2.

References

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Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1949

doi:10.1107/S1600536809027950

Open

access