2-Bromo-4-tert-butyl-6-[(pyridin-2-yl-imino)-meth-yl]phenol.

In the title compound, C(16)H(17)BrN(2)O, the pyridine and benzene rings are almost coplanar [dihedral angle = 1.3 (2)°]. An intra-molecular O-H⋯Br inter-action forms an S(5) ring motif.

Related literature

For the anti-bacterial and anti-tumor activity of substituted salicyl­aldehyde derivatives, see: Jesmin et al. (2010 ▶); Pelttari et al. (2007 ▶) and for the biological activity of 2-amino­pryidine derivatives, see: Hagmann et al. (2000 ▶). For related structures, see: Puthilibai et al. (2008 ▶); Phurat et al. (2010 ▶); Wang et al.(2010 ▶). For the synthesis, see: Pannerselvam et al. (2005 ▶).

Experimental

Crystal data

C16H17BrN2O

M = 333.23

Monoclinic,

a = 10.0241 (11) Å

b = 16.1355 (16) Å

c = 9.4308 (13) Å

β = 92.050 (6)°

V = 1524.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.69 mm−1

T = 293 K

0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

6913 measured reflections

3051 independent reflections

2564 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.081

S = 0.98

3051 reflections

184 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 1147 Friedel pairs

Flack parameter: 0.009 (9)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050148/im2341sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050148/im2341Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050148/im2341Isup3.cml

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

C16H17BrN2O	F(000) = 680
Mr = 333.23	Dx = 1.452 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3053 reflections
a = 10.0241 (11) Å	θ = 2.4–28.3°
b = 16.1355 (16) Å	µ = 2.69 mm−1
c = 9.4308 (13) Å	T = 293 K
β = 92.050 (6)°	Block, red
V = 1524.4 (3) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	2564 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 28.3°, θmin = 2.4°
ω and φ scans	h = −13→13
6913 measured reflections	k = −21→21
3051 independent reflections	l = −12→12

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0327P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
3051 reflections	Δρmax = 0.50 e Å−3
184 parameters	Δρmin = −0.37 e Å−3
2 restraints	Absolute structure: Flack (1983), 1147 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.009 (9)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.5566 (3)	0.96379 (15)	0.4642 (4)	0.0358 (6)
C2	0.6217 (3)	1.03392 (15)	0.5239 (3)	0.0349 (6)
C3	0.5803 (3)	1.11292 (14)	0.4782 (4)	0.0391 (7)
H3	0.6233	1.1589	0.5178	0.047*
C4	0.4795 (3)	1.12589 (15)	0.3781 (4)	0.0361 (6)
C5	0.4150 (3)	1.05601 (17)	0.3224 (4)	0.0379 (7)
H5	0.3454	1.0623	0.2554	0.045*
C6	0.4536 (3)	0.97694 (16)	0.3657 (4)	0.0388 (7)
C7	0.7280 (3)	1.02509 (19)	0.6298 (4)	0.0421 (8)
H7	0.7676	1.0725	0.6684	0.051*
C8	0.8724 (4)	0.94730 (17)	0.7759 (5)	0.0423 (7)
C9	0.9091 (3)	0.8682 (2)	0.8210 (5)	0.0531 (9)
H9	0.8653	0.8219	0.7837	0.064*
C10	1.0103 (4)	0.8595 (3)	0.9207 (5)	0.0653 (11)
H10	1.0367	0.8069	0.9510	0.078*
C11	1.0721 (4)	0.9279 (3)	0.9754 (5)	0.0698 (11)
H11	1.1401	0.9235	1.0447	0.084*
C12	1.0307 (4)	1.0042 (3)	0.9248 (5)	0.0695 (13)
H12	1.0734	1.0511	0.9615	0.083*
C13	0.4388 (3)	1.2146 (2)	0.3348 (4)	0.0436 (8)
C14	0.3815 (4)	1.2584 (2)	0.4631 (5)	0.0662 (10)
H14A	0.3569	1.3140	0.4375	0.099*
H14B	0.4475	1.2596	0.5394	0.099*
H14C	0.3041	1.2289	0.4929	0.099*
C15	0.5606 (3)	1.26226 (17)	0.2862 (5)	0.0564 (9)
H15A	0.5982	1.2340	0.2074	0.085*
H15B	0.6259	1.2656	0.3629	0.085*
H15C	0.5342	1.3171	0.2576	0.085*
C16	0.3336 (4)	1.2144 (3)	0.2134 (6)	0.0654 (12)
H16A	0.3703	1.1896	0.1309	0.098*
H16B	0.3071	1.2704	0.1921	0.098*
H16C	0.2573	1.1832	0.2410	0.098*
Br1	0.36263 (5)	0.884372 (16)	0.28725 (6)	0.06324 (14)
N1	0.7694 (2)	0.95411 (16)	0.6724 (3)	0.0412 (6)
N2	0.9331 (3)	1.01500 (19)	0.8263 (4)	0.0573 (8)
O1	0.5940 (2)	0.88708 (9)	0.5015 (3)	0.0519 (7)
H1	0.5462	0.8533	0.4592	0.078*

	U11	U22	U33	U12	U13	U23
C1	0.0336 (12)	0.0318 (11)	0.0417 (18)	0.0008 (10)	−0.0011 (12)	0.0018 (12)
C2	0.0341 (12)	0.0318 (11)	0.0383 (18)	0.0021 (10)	−0.0067 (12)	0.0026 (12)
C3	0.0421 (14)	0.0292 (12)	0.0452 (19)	0.0002 (10)	−0.0085 (14)	−0.0002 (12)
C4	0.0337 (12)	0.0357 (13)	0.0387 (18)	0.0014 (10)	−0.0023 (13)	0.0025 (13)
C5	0.0330 (13)	0.0400 (14)	0.0401 (18)	−0.0020 (10)	−0.0077 (12)	0.0009 (13)
C6	0.0383 (14)	0.0352 (12)	0.0428 (19)	−0.0049 (11)	0.0003 (13)	−0.0021 (13)
C7	0.0447 (16)	0.0343 (13)	0.047 (2)	0.0019 (11)	−0.0068 (15)	−0.0023 (14)
C8	0.0405 (15)	0.0473 (13)	0.0388 (19)	0.0049 (15)	−0.0022 (13)	0.0061 (18)
C9	0.0532 (19)	0.0542 (18)	0.052 (2)	0.0096 (13)	−0.0039 (16)	0.0086 (16)
C10	0.060 (2)	0.076 (2)	0.059 (3)	0.0227 (19)	−0.003 (2)	0.026 (2)
C11	0.0523 (19)	0.101 (3)	0.055 (2)	0.011 (2)	−0.0214 (17)	0.015 (2)
C12	0.060 (2)	0.081 (3)	0.066 (3)	−0.0077 (19)	−0.024 (2)	0.010 (2)
C13	0.0484 (17)	0.0345 (15)	0.047 (2)	0.0037 (13)	−0.0061 (16)	0.0045 (14)
C14	0.076 (2)	0.0498 (18)	0.074 (3)	0.0211 (16)	0.013 (2)	0.0060 (18)
C15	0.067 (2)	0.0377 (14)	0.064 (3)	−0.0013 (13)	−0.0035 (18)	0.0117 (15)
C16	0.067 (3)	0.051 (2)	0.077 (3)	0.0112 (17)	−0.024 (2)	0.011 (2)
Br1	0.0703 (2)	0.04400 (16)	0.0735 (3)	−0.01579 (16)	−0.02473 (16)	−0.0033 (2)
N1	0.0381 (12)	0.0418 (13)	0.0431 (17)	0.0045 (10)	−0.0089 (11)	0.0036 (11)
N2	0.0525 (15)	0.0573 (16)	0.060 (2)	−0.0037 (12)	−0.0218 (14)	0.0070 (15)
O1	0.0612 (14)	0.0255 (9)	0.0679 (19)	−0.0005 (8)	−0.0146 (13)	0.0030 (9)

C1—O1	1.337 (3)	C10—C11	1.359 (7)
C1—C6	1.380 (4)	C10—H10	0.9300
C1—C2	1.413 (3)	C11—C12	1.378 (6)
C2—C3	1.404 (3)	C11—H11	0.9300
C2—C7	1.441 (5)	C12—N2	1.336 (5)
C3—C4	1.373 (5)	C12—H12	0.9300
C3—H3	0.9300	C13—C16	1.529 (5)
C4—C5	1.393 (4)	C13—C15	1.527 (5)
C4—C13	1.540 (4)	C13—C14	1.531 (6)
C5—C6	1.390 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—Br1	1.887 (3)	C14—H14C	0.9600
C7—N1	1.278 (4)	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—N2	1.330 (5)	C15—H15C	0.9600
C8—C9	1.390 (4)	C16—H16A	0.9600
C8—N1	1.399 (5)	C16—H16B	0.9600
C9—C10	1.366 (6)	C16—H16C	0.9600
C9—H9	0.9300	O1—H1	0.8200
O1—C1—C6	121.0 (3)	C12—C11—H11	121.1
O1—C1—C2	121.0 (3)	N2—C12—C11	124.2 (4)
C6—C1—C2	117.9 (2)	N2—C12—H12	117.9
C3—C2—C1	118.5 (3)	C11—C12—H12	117.9
C3—C2—C7	120.4 (3)	C16—C13—C15	108.3 (3)
C1—C2—C7	121.1 (2)	C16—C13—C14	108.9 (4)
C4—C3—C2	123.5 (2)	C15—C13—C14	109.4 (3)
C4—C3—H3	118.3	C16—C13—C4	111.5 (3)
C2—C3—H3	118.3	C15—C13—C4	110.0 (3)
C3—C4—C5	117.1 (2)	C14—C13—C4	108.8 (3)
C3—C4—C13	120.4 (3)	C13—C14—H14A	109.5
C5—C4—C13	122.5 (3)	C13—C14—H14B	109.5
C6—C5—C4	120.8 (3)	H14A—C14—H14B	109.5
C6—C5—H5	119.6	C13—C14—H14C	109.5
C4—C5—H5	119.6	H14A—C14—H14C	109.5
C1—C6—C5	122.2 (3)	H14B—C14—H14C	109.5
C1—C6—Br1	118.8 (2)	C13—C15—H15A	109.5
C5—C6—Br1	119.1 (2)	C13—C15—H15B	109.5
N1—C7—C2	122.0 (3)	H15A—C15—H15B	109.5
N1—C7—H7	119.0	C13—C15—H15C	109.5
C2—C7—H7	119.0	H15A—C15—H15C	109.5
N2—C8—C9	122.1 (4)	H15B—C15—H15C	109.5
N2—C8—N1	120.1 (3)	C13—C16—H16A	109.5
C9—C8—N1	117.8 (3)	C13—C16—H16B	109.5
C10—C9—C8	119.2 (4)	H16A—C16—H16B	109.5
C10—C9—H9	120.4	C13—C16—H16C	109.5
C8—C9—H9	120.4	H16A—C16—H16C	109.5
C9—C10—C11	119.6 (4)	H16B—C16—H16C	109.5
C9—C10—H10	120.2	C7—N1—C8	120.9 (3)
C11—C10—H10	120.2	C8—N2—C12	117.1 (4)
C10—C11—C12	117.8 (4)	C1—O1—H1	109.5
C10—C11—H11	121.1
O1—C1—C2—C3	178.5 (3)	N2—C8—C9—C10	0.3 (6)
C6—C1—C2—C3	−1.2 (4)	N1—C8—C9—C10	179.3 (3)
O1—C1—C2—C7	−1.8 (4)	C8—C9—C10—C11	0.9 (6)
C6—C1—C2—C7	178.5 (3)	C9—C10—C11—C12	−1.2 (6)
C1—C2—C3—C4	−0.1 (5)	C10—C11—C12—N2	0.5 (7)
C7—C2—C3—C4	−179.8 (3)	C3—C4—C13—C16	175.1 (4)
C2—C3—C4—C5	1.1 (5)	C5—C4—C13—C16	−6.8 (5)
C2—C3—C4—C13	179.4 (3)	C3—C4—C13—C15	55.0 (5)
C3—C4—C5—C6	−1.0 (5)	C5—C4—C13—C15	−126.9 (3)
C13—C4—C5—C6	−179.1 (3)	C3—C4—C13—C14	−64.8 (4)
O1—C1—C6—C5	−178.3 (3)	C5—C4—C13—C14	113.3 (4)
C2—C1—C6—C5	1.4 (5)	C2—C7—N1—C8	−179.8 (3)
O1—C1—C6—Br1	1.6 (4)	N2—C8—N1—C7	−3.3 (5)
C2—C1—C6—Br1	−178.7 (2)	C9—C8—N1—C7	177.7 (3)
C4—C5—C6—C1	−0.3 (5)	C9—C8—N2—C12	−1.0 (6)
C4—C5—C6—Br1	179.8 (2)	N1—C8—N2—C12	−180.0 (3)
C3—C2—C7—N1	−179.1 (3)	C11—C12—N2—C8	0.6 (6)
C1—C2—C7—N1	1.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Br1	0.82	2.46	3.021 (3)	127
C7—H7···N2	0.93	2.38	2.723 (5)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Br1	0.82	2.46	3.021 (3)	127