(E)-4-Bromo-N-(2-chloro­benzyl­idene)­aniline

Wang, C.

doi:10.1107/S1600536811029977

organic compounds

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Volume 67| Part 8| August 2011| Page o2204

doi:10.1107/S1600536811029977

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(E)-4-Bromo-N-(2-chlorobenzylidene)aniline

Chuang Wang ^a ^*

^aState Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: wangchuang119@163.com

(Received 22 July 2011; accepted 25 July 2011; online 30 July 2011)

In the title Schiff base molecule, C₁₃H₉BrClN, the dihedral angle between the benzene rings is 49.8 (2)° and the molecule has an E configuration about the C=N bond. In the crystal, there are no directional interactions but only van der Waals intermolecular interaction forces between neighbouring molecules.

Related literature

For the antibacterial activities of Schiff base compounds, see: El Masry et al. (2000 ). For the anticancer properties of Schiff base compounds, see: Dao et al. (2000 ). For related crystal structures, see: Sun et al. (2011a ,b ); Guo et al. (2011 ). For standard bond-length values, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₉BrClN
M_r = 294.57
Monoclinic, P 2₁ /n
a = 15.243 (13) Å
b = 4.020 (4) Å
c = 20.142 (18) Å
β = 103.248 (8)°
V = 1201.4 (18) Å³
Z = 4
Mo Kα radiation
μ = 3.61 mm⁻¹
T = 296 K
0.25 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.465, T_max = 0.518
7879 measured reflections
2219 independent reflections
1413 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.138
S = 1.04
2219 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029977/su2298sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029977/su2298Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029977/su2298Isup3.cml

checkCIF report

Comment top

Schiff bases compounds have attracted a lot of attention for a long time, because of their applications as antibacterial (El Masry et al., 2000), and anticancer (Dao et al., 2000) agents. We report herein, on the crystal structure of the title new Schiff base compound.

The molecular structure of the title molecule is illustrated in Fig. 1. The geometric parameters agree well with those reported for similar structures (Sun et al., 2011a,b; Guo et al., 2011), and all the bond lengths are within normal ranges (Allen et al., 1987). The dihedral angle between the two aromatic rings in the Schiff base molecule is 49.8 (2)°.

In the crystal, there are only van der Waals intermolecular forces between neighbouring molecules.

Related literature top

For the antibacterial activities of Schiff base compounds, see: El Masry et al. (2000). For the anticancer properties of Schiff base compounds, see: Dao et al. (2000). For related crystal structures, see: Sun et al. (2011a,b); Guo et al. (2011). For standard bond-length values, see: Allen et al. (1987).

Experimental top

A mixture of 2-chlorobenzaldehyde (10 mmol), 4-bromoaniline (10 mmol) and methanol (50 ml) was refluxed for 6 h. It was then allowed to cool and was filtered. Recrystallization of the crude product from methanol yielded colourless crystals, suitable for X-ray diffraction analysis.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 molecule, with atom labels and displacement ellipsoids drawn at the 50% probability level.

(E)-4-Bromo-N-(2-chlorobenzylidene)aniline top

Crystal data top

C₁₃H₉BrClN	F(000) = 584
M_r = 294.57	D_x = 1.629 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1725 reflections
a = 15.243 (13) Å	θ = 2.8–21.7°
b = 4.020 (4) Å	µ = 3.61 mm⁻¹
c = 20.142 (18) Å	T = 296 K
β = 103.248 (8)°	Block, colourless
V = 1201.4 (18) Å³	0.25 × 0.23 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2219 independent reflections
Radiation source: fine-focus sealed tube	1413 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→17
T_min = 0.465, T_max = 0.518	k = −4→4
7879 measured reflections	l = −24→24

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0738P)² + 0.0187P] where P = (F_o² + 2F_c²)/3
2219 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₃H₉BrClN	V = 1201.4 (18) Å³
M_r = 294.57	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.243 (13) Å	µ = 3.61 mm⁻¹
b = 4.020 (4) Å	T = 296 K
c = 20.142 (18) Å	0.25 × 0.23 × 0.21 mm
β = 103.248 (8)°

Data collection top

Bruker APEXII CCD diffractometer	2219 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1413 reflections with I > 2σ(I)
T_min = 0.465, T_max = 0.518	R_int = 0.049
7879 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	Δρ_max = 0.54 e Å⁻³
2219 reflections	Δρ_min = −0.43 e Å⁻³
145 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.

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	0.28006 (4)	0.71850 (15)	1.03703 (3)	0.0824 (3)
C1	0.4330 (3)	0.6328 (11)	0.8929 (2)	0.0499 (11)
H1	0.4917	0.6854	0.8906	0.060*
C2	0.4042 (3)	0.6997 (11)	0.9513 (2)	0.0544 (12)
H2	0.4431	0.8014	0.9880	0.065*
C3	0.3186 (3)	0.6179 (11)	0.9560 (2)	0.0501 (11)
C4	0.2584 (3)	0.4713 (12)	0.9009 (2)	0.0544 (12)
H4	0.2003	0.4154	0.9041	0.065*
C5	0.2870 (3)	0.4110 (12)	0.8416 (2)	0.0527 (12)
H5	0.2469	0.3189	0.8042	0.063*
C6	0.3744 (3)	0.4854 (11)	0.8366 (2)	0.0440 (10)
C7	0.4763 (3)	0.2977 (10)	0.7752 (2)	0.0479 (11)
H7	0.5136	0.2425	0.8171	0.057*
C8	0.5086 (3)	0.2397 (10)	0.7133 (2)	0.0438 (10)
C9	0.4571 (3)	0.3496 (11)	0.6495 (2)	0.0506 (11)
H9	0.4020	0.4532	0.6473	0.061*
C10	0.4871 (4)	0.3061 (12)	0.5909 (3)	0.0603 (13)
H10	0.4520	0.3800	0.5495	0.072*
C11	0.5684 (4)	0.1546 (13)	0.5928 (3)	0.0633 (14)
H11	0.5886	0.1297	0.5528	0.076*
C12	0.6206 (3)	0.0384 (12)	0.6542 (2)	0.0575 (13)
H12	0.6753	−0.0670	0.6557	0.069*
C13	0.5897 (3)	0.0821 (11)	0.7133 (2)	0.0452 (10)
Cl1	0.65673 (8)	−0.0722 (3)	0.78942 (6)	0.0647 (4)
N1	0.3988 (2)	0.4211 (9)	0.77412 (18)	0.0491 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1072 (6)	0.0843 (5)	0.0678 (4)	−0.0119 (3)	0.0453 (4)	−0.0171 (3)
C1	0.046 (2)	0.052 (3)	0.052 (3)	−0.006 (2)	0.011 (2)	0.002 (2)
C2	0.054 (3)	0.057 (3)	0.049 (3)	−0.011 (2)	0.004 (2)	−0.005 (2)
C3	0.061 (3)	0.046 (3)	0.045 (3)	0.002 (2)	0.016 (2)	0.000 (2)
C4	0.043 (2)	0.057 (3)	0.065 (3)	−0.004 (2)	0.015 (2)	−0.010 (2)
C5	0.038 (3)	0.062 (3)	0.053 (3)	0.000 (2)	0.001 (2)	−0.004 (2)
C6	0.048 (3)	0.042 (3)	0.042 (2)	0.006 (2)	0.009 (2)	0.002 (2)
C7	0.047 (3)	0.051 (3)	0.045 (3)	0.000 (2)	0.008 (2)	0.000 (2)
C8	0.044 (2)	0.042 (3)	0.045 (3)	0.000 (2)	0.010 (2)	−0.002 (2)
C9	0.049 (3)	0.054 (3)	0.045 (3)	0.003 (2)	0.003 (2)	0.005 (2)
C10	0.064 (3)	0.065 (3)	0.050 (3)	−0.001 (3)	0.010 (2)	0.004 (2)
C11	0.073 (3)	0.068 (3)	0.053 (3)	−0.006 (3)	0.022 (3)	−0.012 (3)
C12	0.046 (3)	0.062 (3)	0.066 (3)	−0.001 (2)	0.015 (2)	−0.014 (3)
C13	0.043 (2)	0.047 (3)	0.043 (2)	−0.005 (2)	0.005 (2)	−0.005 (2)
Cl1	0.0567 (7)	0.0718 (9)	0.0585 (8)	0.0150 (6)	−0.0019 (6)	−0.0042 (6)
N1	0.046 (2)	0.052 (2)	0.048 (2)	0.0069 (19)	0.0096 (17)	−0.0027 (18)

Geometric parameters (Å, º) top

Br1—C3	1.900 (5)	C7—C8	1.461 (6)
C1—C2	1.374 (6)	C7—H7	0.9300
C1—C6	1.404 (6)	C8—C13	1.390 (6)
C1—H1	0.9300	C8—C9	1.414 (6)
C2—C3	1.369 (7)	C9—C10	1.371 (7)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.399 (6)	C10—C11	1.374 (8)
C4—C5	1.384 (6)	C10—H10	0.9300
C4—H4	0.9300	C11—C12	1.390 (7)
C5—C6	1.391 (6)	C11—H11	0.9300
C5—H5	0.9300	C12—C13	1.387 (6)
C6—N1	1.416 (5)	C12—H12	0.9300
C7—N1	1.276 (5)	C13—Cl1	1.750 (4)

C2—C1—C6	120.3 (4)	C8—C7—H7	118.7
C2—C1—H1	119.9	C13—C8—C9	116.8 (4)
C6—C1—H1	119.9	C13—C8—C7	123.2 (4)
C3—C2—C1	120.6 (4)	C9—C8—C7	120.0 (4)
C3—C2—H2	119.7	C10—C9—C8	121.2 (4)
C1—C2—H2	119.7	C10—C9—H9	119.4
C2—C3—C4	120.6 (4)	C8—C9—H9	119.4
C2—C3—Br1	119.7 (4)	C9—C10—C11	120.7 (5)
C4—C3—Br1	119.7 (3)	C9—C10—H10	119.7
C5—C4—C3	118.7 (4)	C11—C10—H10	119.7
C5—C4—H4	120.7	C10—C11—C12	120.1 (5)
C3—C4—H4	120.7	C10—C11—H11	119.9
C4—C5—C6	121.4 (4)	C12—C11—H11	119.9
C4—C5—H5	119.3	C13—C12—C11	118.9 (4)
C6—C5—H5	119.3	C13—C12—H12	120.5
C5—C6—C1	118.4 (4)	C11—C12—H12	120.5
C5—C6—N1	118.4 (4)	C12—C13—C8	122.4 (4)
C1—C6—N1	123.1 (4)	C12—C13—Cl1	117.5 (3)
N1—C7—C8	122.6 (4)	C8—C13—Cl1	120.1 (3)
N1—C7—H7	118.7	C7—N1—C6	119.1 (4)

C6—C1—C2—C3	1.3 (7)	C7—C8—C9—C10	178.2 (4)
C1—C2—C3—C4	−1.4 (7)	C8—C9—C10—C11	−0.2 (7)
C1—C2—C3—Br1	−179.2 (3)	C9—C10—C11—C12	1.1 (8)
C2—C3—C4—C5	−0.1 (7)	C10—C11—C12—C13	−0.8 (7)
Br1—C3—C4—C5	177.7 (4)	C11—C12—C13—C8	−0.3 (7)
C3—C4—C5—C6	1.6 (7)	C11—C12—C13—Cl1	179.2 (4)
C4—C5—C6—C1	−1.7 (7)	C9—C8—C13—C12	1.2 (6)
C4—C5—C6—N1	−179.3 (4)	C7—C8—C13—C12	−178.0 (4)
C2—C1—C6—C5	0.2 (6)	C9—C8—C13—Cl1	−178.4 (3)
C2—C1—C6—N1	177.7 (4)	C7—C8—C13—Cl1	2.5 (6)
N1—C7—C8—C13	−174.9 (4)	C8—C7—N1—C6	−176.8 (4)
N1—C7—C8—C9	6.0 (6)	C5—C6—N1—C7	−139.1 (4)
C13—C8—C9—C10	−1.0 (7)	C1—C6—N1—C7	43.5 (6)

Experimental details

Crystal data
Chemical formula	C₁₃H₉BrClN
M_r	294.57
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	15.243 (13), 4.020 (4), 20.142 (18)
β (°)	103.248 (8)
V (Å³)	1201.4 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.61
Crystal size (mm)	0.25 × 0.23 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.465, 0.518
No. of measured, independent and observed [I > 2σ(I)] reflections	7879, 2219, 1413
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.138, 1.04
No. of reflections	2219
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.43

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author wishes to thank Professor Shao, Lanzhou University, for collecting the X-ray diffraction data.

References

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