N-[(E)-4-Bromo-benzyl-idene]-3,4-di-methyl-aniline.

In the title compound, C15H14BrN, the dihedral angle between the benzene rings is 6.4 (2)° and the mol-ecule has an E conformation about the C=N bond. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming two-dimensional networks lying parallel to (001).

Related literature

Schiff bases derivatives have many pharmaceutical activities. For their anti­fungal properties, see: Aziz et al. (2010 ▶), for their radical scavenging activity, see: Lu et al. (2012 ▶), for their inhibition of enzyme activity, see: Schmidt et al. (2009 ▶) and for their anti­bacterial activity, see: Shi et al. (2010 ▶). For related structures, see: Sun et al. (2011a ▶,b ▶); Guo et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14BrN

M = 288.18

Orthorhombic,

a = 14.868 (7) Å

b = 6.161 (3) Å

c = 28.609 (13) Å

V = 2621 (2) Å3

Z = 8

Mo Kα radiation

μ = 3.11 mm−1

T = 296 K

0.22 × 0.19 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.547, T max = 0.670

17312 measured reflections

2445 independent reflections

1438 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.148

S = 1.03

2445 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAIn class="Chemical">NT (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008143/su2579sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008143/su2579Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008143/su2579Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14BrN	F(000) = 1168
Mr = 288.18	Dx = 1.461 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2443 reflections
a = 14.868 (7) Å	θ = 2.7–25.5°
b = 6.161 (3) Å	µ = 3.11 mm−1
c = 28.609 (13) Å	T = 296 K
V = 2621 (2) Å3	Block, yellow
Z = 8	0.22 × 0.19 × 0.14 mm

Bruker APEXII CCD diffractometer	2445 independent reflections
Radiation source: fine-focus sealed tube	1438 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
φ and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.547, Tmax = 0.670	k = −7→7
17312 measured reflections	l = −32→34

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0449P)2 + 6.739P] where P = (Fo2 + 2Fc2)/3
2445 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
Br1	0.12941 (5)	1.15486 (14)	0.55818 (2)	0.0821 (3)
N1	0.1277 (3)	0.5957 (7)	0.76719 (15)	0.0460 (16)
C1	0.1549 (3)	0.7560 (9)	0.6734 (2)	0.0507 (19)
C2	0.1579 (4)	0.8357 (11)	0.6281 (2)	0.058 (2)
C3	0.1256 (3)	1.0405 (10)	0.62021 (17)	0.0460 (19)
C4	0.0911 (4)	1.1681 (10)	0.65516 (19)	0.0533 (19)
C5	0.0907 (4)	1.0843 (9)	0.70019 (19)	0.0523 (19)
C6	0.1210 (3)	0.8791 (9)	0.70960 (18)	0.0417 (17)
C7	0.1164 (3)	0.7919 (9)	0.75771 (19)	0.0470 (19)
C8	0.1253 (3)	0.5192 (8)	0.81399 (16)	0.0387 (16)
C9	0.0878 (3)	0.6300 (8)	0.85173 (18)	0.0430 (17)
C10	0.0929 (3)	0.5490 (9)	0.89694 (18)	0.0440 (17)
C11	0.1357 (3)	0.3504 (9)	0.90483 (19)	0.0477 (17)
C12	0.1714 (3)	0.2393 (9)	0.8668 (2)	0.0477 (19)
C13	0.1656 (3)	0.3213 (8)	0.8222 (2)	0.0443 (17)
C14	0.0523 (5)	0.6765 (11)	0.93710 (19)	0.072 (3)
C15	0.1459 (4)	0.2609 (11)	0.9540 (2)	0.070 (2)
H1	0.17610	0.61680	0.67950	0.0610*
H2	0.18130	0.75260	0.60390	0.0690*
H4	0.06880	1.30610	0.64890	0.0640*
H5	0.06940	1.16980	0.72460	0.0630*
H7	0.10450	0.88760	0.78210	0.0560*
H9	0.05860	0.76120	0.84650	0.0520*
H12	0.19980	0.10660	0.87160	0.0570*
H13	0.18910	0.24250	0.79730	0.0530*
H14A	0.00220	0.59760	0.94980	0.1080*
H14B	0.03200	0.81510	0.92590	0.1080*
H14C	0.09680	0.69750	0.96100	0.1080*
H15A	0.17400	0.36800	0.97350	0.1050*
H15B	0.18250	0.13260	0.95320	0.1050*
H15C	0.08770	0.22570	0.96640	0.1050*

	U11	U22	U33	U12	U13	U23
Br1	0.0956 (5)	0.1062 (6)	0.0446 (4)	−0.0111 (5)	−0.0052 (3)	0.0232 (4)
N1	0.045 (2)	0.049 (3)	0.044 (3)	−0.001 (2)	−0.001 (2)	0.000 (2)
C1	0.049 (3)	0.044 (3)	0.059 (4)	0.009 (3)	−0.003 (3)	0.004 (3)
C2	0.059 (3)	0.067 (5)	0.047 (4)	0.007 (3)	0.000 (3)	−0.004 (3)
C3	0.044 (3)	0.063 (4)	0.031 (3)	−0.008 (3)	−0.007 (2)	0.009 (3)
C4	0.065 (3)	0.049 (4)	0.046 (3)	−0.002 (3)	−0.008 (3)	0.006 (3)
C5	0.060 (3)	0.052 (4)	0.045 (3)	0.001 (3)	0.001 (3)	−0.004 (3)
C6	0.041 (3)	0.043 (3)	0.041 (3)	−0.007 (3)	−0.001 (2)	−0.001 (2)
C7	0.052 (3)	0.047 (4)	0.042 (3)	−0.003 (3)	−0.007 (2)	−0.005 (3)
C8	0.037 (2)	0.041 (3)	0.038 (3)	−0.003 (3)	−0.002 (2)	0.000 (2)
C9	0.043 (3)	0.037 (3)	0.049 (3)	0.008 (2)	0.001 (2)	0.004 (3)
C10	0.041 (3)	0.042 (3)	0.049 (3)	−0.004 (3)	−0.003 (2)	−0.005 (3)
C11	0.046 (3)	0.047 (3)	0.050 (3)	−0.004 (3)	−0.004 (3)	0.006 (3)
C12	0.036 (3)	0.035 (3)	0.072 (4)	0.005 (2)	−0.002 (3)	0.006 (3)
C13	0.042 (3)	0.039 (3)	0.052 (3)	0.000 (2)	0.003 (2)	−0.003 (3)
C14	0.090 (5)	0.076 (5)	0.050 (4)	0.013 (4)	0.004 (3)	−0.008 (3)
C15	0.075 (4)	0.073 (4)	0.061 (4)	0.012 (3)	−0.002 (3)	0.017 (3)

Br1—C3	1.910 (5)	C11—C15	1.519 (8)
N1—C7	1.250 (7)	C12—C13	1.375 (8)
N1—C8	1.420 (6)	C1—H1	0.9300
C1—C2	1.387 (8)	C2—H2	0.9300
C1—C6	1.379 (8)	C4—H4	0.9300
C2—C3	1.369 (9)	C5—H5	0.9300
C3—C4	1.372 (8)	C7—H7	0.9300
C4—C5	1.388 (8)	C9—H9	0.9300
C5—C6	1.369 (8)	C12—H12	0.9300
C6—C7	1.479 (8)	C13—H13	0.9300
C8—C9	1.394 (7)	C14—H14A	0.9600
C8—C13	1.379 (7)	C14—H14B	0.9600
C9—C10	1.388 (7)	C14—H14C	0.9600
C10—C11	1.398 (8)	C15—H15A	0.9600
C10—C14	1.517 (8)	C15—H15B	0.9600
C11—C12	1.391 (8)	C15—H15C	0.9600
C7—N1—C8	121.5 (5)	C1—C2—H2	121.00
C2—C1—C6	121.3 (5)	C3—C2—H2	121.00
C1—C2—C3	118.0 (5)	C3—C4—H4	121.00
Br1—C3—C2	118.9 (4)	C5—C4—H4	121.00
Br1—C3—C4	118.5 (4)	C4—C5—H5	119.00
C2—C3—C4	122.6 (5)	C6—C5—H5	119.00
C3—C4—C5	117.7 (5)	N1—C7—H7	118.00
C4—C5—C6	121.7 (5)	C6—C7—H7	118.00
C1—C6—C5	118.7 (5)	C8—C9—H9	119.00
C1—C6—C7	121.1 (5)	C10—C9—H9	119.00
C5—C6—C7	120.2 (5)	C11—C12—H12	119.00
N1—C7—C6	123.2 (5)	C13—C12—H12	119.00
N1—C8—C9	125.3 (4)	C8—C13—H13	120.00
N1—C8—C13	116.3 (4)	C12—C13—H13	120.00
C9—C8—C13	118.4 (5)	C10—C14—H14A	109.00
C8—C9—C10	121.6 (5)	C10—C14—H14B	109.00
C9—C10—C11	119.3 (5)	C10—C14—H14C	110.00
C9—C10—C14	119.9 (5)	H14A—C14—H14B	109.00
C11—C10—C14	120.8 (5)	H14A—C14—H14C	109.00
C10—C11—C12	118.6 (5)	H14B—C14—H14C	110.00
C10—C11—C15	120.9 (5)	C11—C15—H15A	109.00
C12—C11—C15	120.5 (5)	C11—C15—H15B	109.00
C11—C12—C13	121.4 (5)	C11—C15—H15C	110.00
C8—C13—C12	120.7 (5)	H15A—C15—H15B	109.00
C2—C1—H1	119.00	H15A—C15—H15C	109.00
C6—C1—H1	119.00	H15B—C15—H15C	109.00
C7—N1—C8—C13	−160.1 (5)	C5—C6—C7—N1	166.9 (5)
C8—N1—C7—C6	178.2 (4)	N1—C8—C9—C10	−176.2 (4)
C7—N1—C8—C9	18.2 (7)	C13—C8—C9—C10	2.1 (7)
C2—C1—C6—C5	−0.6 (8)	N1—C8—C13—C12	176.2 (4)
C6—C1—C2—C3	−0.4 (8)	C9—C8—C13—C12	−2.3 (7)
C2—C1—C6—C7	178.9 (5)	C8—C9—C10—C11	−0.8 (7)
C1—C2—C3—Br1	179.7 (4)	C8—C9—C10—C14	179.1 (5)
C1—C2—C3—C4	0.2 (8)	C9—C10—C11—C12	−0.4 (7)
Br1—C3—C4—C5	−178.6 (4)	C9—C10—C11—C15	177.5 (5)
C2—C3—C4—C5	0.9 (8)	C14—C10—C11—C12	179.7 (5)
C3—C4—C5—C6	−1.9 (9)	C14—C10—C11—C15	−2.4 (7)
C4—C5—C6—C1	1.8 (8)	C10—C11—C12—C13	0.3 (7)
C4—C5—C6—C7	−177.7 (5)	C15—C11—C12—C13	−177.7 (5)
C1—C6—C7—N1	−12.5 (7)	C11—C12—C13—C8	1.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1i	0.93	2.99	3.773 (5)	143
C12—H12···Cg2ii	0.93	2.77	3.507 (5)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg1i	0.93	2.99	3.773 (5)	143
C12—H12⋯Cg2ii	0.93	2.77	3.507 (5)	137

Symmetry codes: (i) ; (ii) .