4-Bromo-2-{[(pyridin-3-ylmeth-yl)imino]-meth-yl}phenol.

The title compound, C(13)H(11)BrN(2)O, is a polydentate Schiff base and reveals intra-molecular O-H⋯N hydrogen bonding between the hy-droxy O atom and the imino N atom. The dihedral angle between the aromatic ring and the pyridyl ring is 71.7 (1)°. In the crystal, the mol-ecules are stacked in columns along the c axis and several inter-molecular π-π inter-actions are present between the six-membered rings, with a shortest centroid-centroid distance of 3.707 (2) Å.

Related literature

For the crystal structure of 4-bromo-2-{[(pyridin-2-ylmethyl)imino]methyl}phenol, see: Zhang et al. (2003 ▶).

Experimental

Crystal data

C13H11BrN2O

M = 291.15

Monoclinic,

a = 14.0947 (19) Å

b = 6.0994 (8) Å

c = 14.0373 (19) Å

β = 103.704 (3)°

V = 1172.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.49 mm−1

T = 200 K

0.30 × 0.22 × 0.14 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.833, T max = 1.000

8297 measured reflections

2906 independent reflections

1859 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.099

S = 1.13

2906 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.84 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003011/ng5109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003011/ng5109Isup2.hkl

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

C13H11BrN2O	F(000) = 584
Mr = 291.15	Dx = 1.649 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3009 reflections
a = 14.0947 (19) Å	θ = 3.0–27.0°
b = 6.0994 (8) Å	µ = 3.49 mm−1
c = 14.0373 (19) Å	T = 200 K
β = 103.704 (3)°	Block, yellow
V = 1172.4 (3) Å3	0.30 × 0.22 × 0.14 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	2906 independent reflections
Radiation source: fine-focus sealed tube	1859 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 28.3°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→17
Tmin = 0.833, Tmax = 1.000	k = −8→8
8297 measured reflections	l = −13→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0134P)2 + 2.5694P] where P = (Fo2 + 2Fc2)/3
2906 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.84 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	0.76468 (3)	0.70338 (8)	0.44621 (4)	0.04693 (16)
O1	0.3873 (2)	0.1972 (5)	0.3696 (2)	0.0395 (7)
H1	0.332 (4)	0.283 (9)	0.338 (4)	0.081 (18)*
N1	0.3004 (2)	0.5487 (6)	0.2840 (2)	0.0353 (8)
N2	0.0887 (2)	0.9342 (6)	0.4172 (3)	0.0416 (9)
C1	0.4726 (3)	0.5284 (6)	0.3484 (3)	0.0267 (8)
C2	0.4714 (3)	0.3123 (6)	0.3834 (3)	0.0281 (8)
C3	0.5585 (3)	0.2149 (7)	0.4341 (3)	0.0338 (9)
H3	0.5578	0.0687	0.4574	0.041*
C4	0.6450 (3)	0.3279 (7)	0.4507 (3)	0.0338 (9)
H4	0.7038	0.2606	0.4855	0.041*
C5	0.6462 (3)	0.5405 (7)	0.4164 (3)	0.0307 (9)
C6	0.5623 (3)	0.6397 (7)	0.3654 (3)	0.0307 (9)
H6	0.5649	0.7845	0.3413	0.037*
C7	0.3835 (3)	0.6408 (7)	0.2984 (3)	0.0307 (9)
H7	0.3876	0.7867	0.2761	0.037*
C8	0.2146 (3)	0.6772 (8)	0.2349 (3)	0.0412 (10)
H8A	0.1805	0.6019	0.1740	0.049*
H8B	0.2358	0.8231	0.2169	0.049*
C9	0.1454 (2)	0.7050 (7)	0.3019 (3)	0.0317 (8)
C10	0.1465 (3)	0.8949 (7)	0.3555 (3)	0.0391 (10)
H10	0.1915	1.0061	0.3483	0.047*
C11	0.0261 (3)	0.7758 (7)	0.4251 (3)	0.0378 (10)
H11	−0.0164	0.7995	0.4675	0.045*
C12	0.0194 (3)	0.5796 (7)	0.3754 (3)	0.0385 (10)
H12	−0.0261	0.4709	0.3842	0.046*
C13	0.0800 (3)	0.5436 (7)	0.3127 (3)	0.0373 (10)
H13	0.0766	0.4098	0.2774	0.045*

	U11	U22	U33	U12	U13	U23
Br1	0.0307 (2)	0.0546 (3)	0.0530 (3)	−0.0087 (2)	0.00510 (18)	0.0004 (2)
O1	0.0347 (15)	0.0333 (16)	0.0524 (19)	−0.0090 (13)	0.0140 (14)	0.0004 (15)
N1	0.0286 (16)	0.043 (2)	0.0354 (19)	0.0039 (15)	0.0092 (15)	−0.0030 (16)
N2	0.0347 (18)	0.046 (2)	0.047 (2)	−0.0025 (16)	0.0159 (17)	−0.0081 (18)
C1	0.0302 (19)	0.027 (2)	0.0246 (19)	−0.0023 (15)	0.0093 (16)	−0.0021 (15)
C2	0.0327 (19)	0.030 (2)	0.0245 (19)	−0.0043 (17)	0.0121 (16)	−0.0047 (17)
C3	0.041 (2)	0.033 (2)	0.032 (2)	0.0032 (18)	0.0174 (18)	0.0026 (18)
C4	0.035 (2)	0.040 (3)	0.028 (2)	0.0048 (18)	0.0087 (17)	0.0010 (18)
C5	0.0261 (18)	0.038 (2)	0.030 (2)	−0.0020 (16)	0.0106 (16)	−0.0028 (17)
C6	0.035 (2)	0.031 (2)	0.028 (2)	−0.0013 (16)	0.0114 (17)	0.0003 (16)
C7	0.035 (2)	0.033 (2)	0.026 (2)	0.0058 (17)	0.0119 (17)	−0.0034 (16)
C8	0.031 (2)	0.057 (3)	0.035 (2)	0.010 (2)	0.0053 (18)	0.002 (2)
C9	0.0216 (17)	0.040 (2)	0.031 (2)	0.0056 (17)	0.0015 (15)	−0.0001 (19)
C10	0.029 (2)	0.042 (3)	0.046 (3)	−0.0068 (18)	0.0092 (19)	−0.004 (2)
C11	0.0271 (19)	0.050 (3)	0.038 (2)	−0.0008 (19)	0.0098 (17)	−0.001 (2)
C12	0.034 (2)	0.042 (3)	0.041 (2)	−0.0079 (19)	0.0106 (19)	0.006 (2)
C13	0.039 (2)	0.036 (2)	0.033 (2)	−0.0008 (19)	0.0008 (18)	−0.0017 (18)

Br1—C5	1.903 (4)	C5—C6	1.369 (5)
O1—C2	1.352 (4)	C6—H6	0.9500
O1—H1	0.96 (5)	C7—H7	0.9500
N1—C7	1.271 (5)	C8—C9	1.517 (5)
N1—C8	1.468 (5)	C8—H8A	0.9900
N2—C11	1.331 (5)	C8—H8B	0.9900
N2—C10	1.344 (5)	C9—C10	1.379 (6)
C1—C6	1.406 (5)	C9—C13	1.381 (5)
C1—C2	1.408 (5)	C10—H10	0.9500
C1—C7	1.456 (5)	C11—C12	1.377 (6)
C2—C3	1.397 (5)	C11—H11	0.9500
C3—C4	1.372 (5)	C12—C13	1.382 (6)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.384 (5)	C13—H13	0.9500
C4—H4	0.9500
C2—O1—H1	112 (3)	C1—C7—H7	119.2
C7—N1—C8	117.6 (4)	N1—C8—C9	110.4 (3)
C11—N2—C10	116.1 (4)	N1—C8—H8A	109.6
C6—C1—C2	118.5 (3)	C9—C8—H8A	109.6
C6—C1—C7	119.5 (3)	N1—C8—H8B	109.6
C2—C1—C7	121.9 (3)	C9—C8—H8B	109.6
O1—C2—C3	119.1 (4)	H8A—C8—H8B	108.1
O1—C2—C1	121.2 (3)	C10—C9—C13	117.4 (4)
C3—C2—C1	119.6 (3)	C10—C9—C8	120.4 (4)
C4—C3—C2	120.7 (4)	C13—C9—C8	122.2 (4)
C4—C3—H3	119.6	N2—C10—C9	124.8 (4)
C2—C3—H3	119.6	N2—C10—H10	117.6
C3—C4—C5	119.7 (4)	C9—C10—H10	117.6
C3—C4—H4	120.2	N2—C11—C12	123.8 (4)
C5—C4—H4	120.2	N2—C11—H11	118.1
C6—C5—C4	121.0 (4)	C12—C11—H11	118.1
C6—C5—Br1	119.2 (3)	C11—C12—C13	118.8 (4)
C4—C5—Br1	119.7 (3)	C11—C12—H12	120.6
C5—C6—C1	120.4 (4)	C13—C12—H12	120.6
C5—C6—H6	119.8	C9—C13—C12	119.1 (4)
C1—C6—H6	119.8	C9—C13—H13	120.5
N1—C7—C1	121.7 (4)	C12—C13—H13	120.5
N1—C7—H7	119.2
C6—C1—C2—O1	179.8 (3)	C6—C1—C7—N1	−178.0 (4)
C7—C1—C2—O1	1.8 (5)	C2—C1—C7—N1	0.0 (5)
C6—C1—C2—C3	0.4 (5)	C7—N1—C8—C9	−118.3 (4)
C7—C1—C2—C3	−177.6 (3)	N1—C8—C9—C10	98.1 (5)
O1—C2—C3—C4	−179.0 (3)	N1—C8—C9—C13	−81.3 (5)
C1—C2—C3—C4	0.4 (5)	C11—N2—C10—C9	−0.4 (6)
C2—C3—C4—C5	−0.3 (6)	C13—C9—C10—N2	−0.1 (6)
C3—C4—C5—C6	−0.6 (6)	C8—C9—C10—N2	−179.5 (4)
C3—C4—C5—Br1	176.2 (3)	C10—N2—C11—C12	0.8 (6)
C4—C5—C6—C1	1.3 (6)	N2—C11—C12—C13	−0.7 (6)
Br1—C5—C6—C1	−175.5 (3)	C10—C9—C13—C12	0.2 (6)
C2—C1—C6—C5	−1.2 (5)	C8—C9—C13—C12	179.6 (4)
C7—C1—C6—C5	176.8 (3)	C11—C12—C13—C9	0.2 (6)
C8—N1—C7—C1	178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.96 (5)	1.80 (5)	2.616 (5)	141 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.96 (5)	1.80 (5)	2.616 (5)	141 (5)