(E)-N-[(6-Bromo-pyridin-2-yl)methyl-idene]-4-methyl-aniline.

The title compound, C(13)H(11)BrN(2), a Schiff base obtained from 6-bromo-picolinaldehyde and p-toluidine, has an E configuration about the C=N bond. The dihedral angle between the benzene and pyridine rings is 30.4 (1)°.

Related literature

For Schiff base complexes with transition metals, see: Burkhardt & Plass (2008 ▶); Keypour et al. (2011 ▶); Tarafder et al. (2002 ▶). For their complexing ability towards toxic metals, see: Kocyigit et al. (2010 ▶);

Experimental

Crystal data

C13H11BrN2

M = 275.15

Orthorhombic,

a = 13.542 (3) Å

b = 6.1544 (15) Å

c = 27.620 (7) Å

V = 2301.9 (10) Å3

Z = 8

Mo Kα radiation

μ = 3.54 mm−1

T = 113 K

0.20 × 0.08 × 0.04 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 ▶) T min = 0.538, T max = 0.871

21379 measured reflections

2750 independent reflections

2251 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.08

2750 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.91 e Å−3

Δρmin = −0.66 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Crystal Impact, 2009 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031825/ld2022sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031825/ld2022Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031825/ld2022Isup3.cml

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

C13H11BrN2	Dx = 1.588 Mg m−3
Mr = 275.15	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 6762 reflections
a = 13.542 (3) Å	θ = 2.1–28.0°
b = 6.1544 (15) Å	µ = 3.54 mm−1
c = 27.620 (7) Å	T = 113 K
V = 2301.9 (10) Å3	Prism, colorless
Z = 8	0.20 × 0.08 × 0.04 mm
F(000) = 1104

Rigaku Saturn724 CCD diffractometer	2750 independent reflections
Radiation source: rotating anode	2251 reflections with I > 2σ(I)
multilayer	Rint = 0.044
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 2.1°
ω and φ scans	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	k = −7→8
Tmin = 0.538, Tmax = 0.871	l = −36→36
21379 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0529P)2] where P = (Fo2 + 2Fc2)/3
2750 reflections	(Δ/σ)max = 0.002
146 parameters	Δρmax = 0.91 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.38420 (2)	0.10293 (5)	0.750452 (7)	0.03018 (13)
N1	0.38367 (13)	0.1724 (3)	0.65201 (6)	0.0218 (4)
N2	0.38262 (12)	0.2660 (3)	0.52490 (7)	0.0219 (4)
C1	0.37666 (14)	0.2783 (4)	0.69322 (8)	0.0215 (5)
C2	0.36569 (15)	0.5001 (4)	0.69829 (8)	0.0247 (5)
H2	0.3618	0.5667	0.7293	0.030*
C3	0.36066 (16)	0.6208 (4)	0.65619 (9)	0.0250 (5)
H3	0.3531	0.7742	0.6576	0.030*
C4	0.36681 (14)	0.5157 (4)	0.61200 (8)	0.0224 (5)
H4	0.3629	0.5959	0.5827	0.027*
C5	0.37868 (14)	0.2921 (4)	0.61109 (8)	0.0209 (5)
C6	0.38647 (15)	0.1703 (4)	0.56563 (8)	0.0221 (5)
H6	0.3945	0.0171	0.5666	0.027*
C7	0.38278 (14)	0.1445 (4)	0.48137 (8)	0.0219 (5)
C8	0.41670 (16)	0.2481 (4)	0.43969 (7)	0.0234 (5)
H8	0.4428	0.3912	0.4417	0.028*
C9	0.41266 (17)	0.1437 (4)	0.39534 (8)	0.0272 (5)
H9	0.4372	0.2151	0.3673	0.033*
C10	0.37303 (14)	−0.0649 (4)	0.39118 (9)	0.0228 (5)
C11	0.33938 (16)	−0.1659 (4)	0.43272 (8)	0.0246 (5)
H11	0.3123	−0.3079	0.4305	0.030*
C12	0.34413 (15)	−0.0651 (4)	0.47738 (8)	0.0224 (5)
H12	0.3211	−0.1387	0.5054	0.027*
C14	0.36452 (17)	−0.1756 (5)	0.34244 (9)	0.0332 (6)
H14A	0.2966	−0.1623	0.3305	0.050*
H14B	0.3816	−0.3296	0.3458	0.050*
H14C	0.4098	−0.1065	0.3195	0.050*

	U11	U22	U33	U12	U13	U23
Br1	0.0412 (2)	0.0310 (2)	0.01834 (17)	0.00145 (10)	−0.00218 (9)	0.00303 (9)
N1	0.0239 (10)	0.0212 (11)	0.0203 (10)	0.0009 (7)	−0.0008 (7)	0.0006 (8)
N2	0.0218 (10)	0.0232 (12)	0.0207 (10)	−0.0010 (8)	0.0013 (7)	−0.0021 (8)
C1	0.0207 (11)	0.0236 (13)	0.0202 (11)	−0.0007 (9)	−0.0009 (8)	0.0007 (9)
C2	0.0257 (12)	0.0267 (14)	0.0217 (12)	−0.0008 (9)	0.0000 (9)	−0.0063 (10)
C3	0.0302 (13)	0.0200 (13)	0.0247 (13)	0.0017 (9)	−0.0008 (9)	−0.0018 (10)
C4	0.0251 (11)	0.0218 (14)	0.0203 (12)	0.0004 (9)	0.0011 (8)	0.0012 (10)
C5	0.0180 (11)	0.0243 (13)	0.0203 (11)	0.0000 (9)	0.0000 (7)	0.0003 (10)
C6	0.0234 (11)	0.0196 (13)	0.0234 (12)	0.0022 (9)	−0.0011 (8)	−0.0026 (9)
C7	0.0177 (11)	0.0277 (14)	0.0202 (12)	0.0034 (9)	−0.0005 (8)	−0.0002 (9)
C8	0.0229 (11)	0.0228 (13)	0.0246 (11)	−0.0002 (9)	0.0027 (9)	0.0034 (9)
C9	0.0245 (12)	0.0361 (15)	0.0209 (11)	−0.0004 (10)	0.0042 (9)	0.0034 (10)
C10	0.0182 (11)	0.0300 (14)	0.0201 (12)	0.0019 (9)	−0.0004 (8)	−0.0048 (10)
C11	0.0223 (11)	0.0236 (13)	0.0279 (12)	−0.0002 (9)	−0.0030 (9)	−0.0026 (9)
C12	0.0226 (11)	0.0231 (13)	0.0214 (11)	−0.0010 (9)	−0.0011 (8)	0.0028 (9)
C14	0.0325 (14)	0.0452 (17)	0.0220 (13)	−0.0019 (11)	−0.0001 (9)	−0.0088 (12)

Br1—C1	1.917 (2)	C7—C8	1.394 (3)
N1—C1	1.316 (3)	C7—C12	1.397 (3)
N1—C5	1.351 (3)	C8—C9	1.384 (3)
N2—C6	1.271 (3)	C8—H8	0.9500
N2—C7	1.416 (3)	C9—C10	1.397 (3)
C1—C2	1.380 (3)	C9—H9	0.9500
C2—C3	1.382 (3)	C10—C11	1.382 (3)
C2—H2	0.9500	C10—C14	1.513 (3)
C3—C4	1.384 (3)	C11—C12	1.382 (3)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.386 (4)	C12—H12	0.9500
C4—H4	0.9500	C14—H14A	0.9800
C5—C6	1.466 (3)	C14—H14B	0.9800
C6—H6	0.9500	C14—H14C	0.9800
C1—N1—C5	116.7 (2)	C12—C7—N2	123.7 (2)
C6—N2—C7	120.5 (2)	C9—C8—C7	120.4 (2)
N1—C1—C2	125.9 (2)	C9—C8—H8	119.8
N1—C1—Br1	115.50 (17)	C7—C8—H8	119.8
C2—C1—Br1	118.63 (17)	C8—C9—C10	121.0 (2)
C1—C2—C3	116.8 (2)	C8—C9—H9	119.5
C1—C2—H2	121.6	C10—C9—H9	119.5
C3—C2—H2	121.6	C11—C10—C9	118.2 (2)
C2—C3—C4	119.2 (2)	C11—C10—C14	120.8 (2)
C2—C3—H3	120.4	C9—C10—C14	121.1 (2)
C4—C3—H3	120.4	C10—C11—C12	121.6 (2)
C3—C4—C5	119.1 (2)	C10—C11—H11	119.2
C3—C4—H4	120.4	C12—C11—H11	119.2
C5—C4—H4	120.4	C11—C12—C7	120.1 (2)
N1—C5—C4	122.2 (2)	C11—C12—H12	119.9
N1—C5—C6	115.7 (2)	C7—C12—H12	119.9
C4—C5—C6	122.1 (2)	C10—C14—H14A	109.5
N2—C6—C5	121.2 (2)	C10—C14—H14B	109.5
N2—C6—H6	119.4	H14A—C14—H14B	109.5
C5—C6—H6	119.4	C10—C14—H14C	109.5
C8—C7—C12	118.7 (2)	H14A—C14—H14C	109.5
C8—C7—N2	117.4 (2)	H14B—C14—H14C	109.5
C5—N1—C1—C2	−0.7 (3)	C6—N2—C7—C8	−155.5 (2)
C5—N1—C1—Br1	−179.94 (14)	C6—N2—C7—C12	29.6 (3)
N1—C1—C2—C3	0.7 (3)	C12—C7—C8—C9	−0.5 (3)
Br1—C1—C2—C3	179.93 (15)	N2—C7—C8—C9	−175.66 (19)
C1—C2—C3—C4	−0.1 (3)	C7—C8—C9—C10	1.2 (3)
C2—C3—C4—C5	−0.5 (3)	C8—C9—C10—C11	−1.0 (3)
C1—N1—C5—C4	0.0 (3)	C8—C9—C10—C14	177.4 (2)
C1—N1—C5—C6	−179.88 (17)	C9—C10—C11—C12	0.1 (3)
C3—C4—C5—N1	0.6 (3)	C14—C10—C11—C12	−178.3 (2)
C3—C4—C5—C6	−179.54 (19)	C10—C11—C12—C7	0.6 (3)
C7—N2—C6—C5	−175.22 (17)	C8—C7—C12—C11	−0.4 (3)
N1—C5—C6—N2	179.92 (19)	N2—C7—C12—C11	174.45 (19)
C4—C5—C6—N2	0.0 (3)