(E)-2-[1-(3-Amino-4-chloro-phenyl-imino)eth-yl]-4-bromo-phenol.

The title Schiff base compound, C(14)H(12)BrClN(2)O, exists in an E configuration with respect to the central C=N double bond. The amino group adopts a pyramidal configuration. The dihedral angle between the two benzene rings is 76.88 (10)° and an intra-molecular O-H⋯N hydrogen bond forms a six-membered ring, generating an S(6) ring motif. In the crystal structure, mol-ecules are linked into chains along [010] via N-H⋯O hydrogen bonds. The presence of π-π inter-actions [centroid-centroid distance = 3.6244 (12) Å] further stabilizes the crystal structure.

Related literature

For the biological activity and corrosion inhibition properties of Schiff base derivatives, see: Azam et al. (2007 ▶); Sauri et al. (2009 ▶). For a related structure, see: Yamin et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H12BrClN2O

M = 339.62

Monoclinic,

a = 10.2469 (1) Å

b = 8.7672 (1) Å

c = 15.7180 (2) Å

β = 107.065 (1)°

V = 1349.88 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.24 mm−1

T = 296 K

0.24 × 0.22 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.509, T max = 0.726

14782 measured reflections

3925 independent reflections

2420 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.077

S = 1.00

3925 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009773/tk2641sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009773/tk2641Isup2.hkl

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

C14H12BrClN2O	F(000) = 680
Mr = 339.62	Dx = 1.671 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4343 reflections
a = 10.2469 (1) Å	θ = 2.7–28.5°
b = 8.7672 (1) Å	µ = 3.24 mm−1
c = 15.7180 (2) Å	T = 296 K
β = 107.065 (1)°	Block, yellow
V = 1349.88 (3) Å3	0.24 × 0.22 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3925 independent reflections
Radiation source: fine-focus sealed tube	2420 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.509, Tmax = 0.726	k = −12→9
14782 measured reflections	l = −22→21

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0299P)2 + 0.2742P] where P = (Fo2 + 2Fc2)/3
3925 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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 > 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	0.82408 (3)	0.92283 (3)	0.233924 (15)	0.05982 (11)
Cl1	0.55171 (6)	1.10458 (7)	0.92352 (4)	0.05352 (17)
O1	0.92270 (16)	1.31628 (18)	0.55948 (10)	0.0499 (4)
N1	0.76555 (17)	1.1434 (2)	0.61354 (10)	0.0391 (4)
N2	0.7688 (2)	0.9064 (2)	0.89348 (14)	0.0503 (5)
C1	0.9012 (2)	1.2211 (2)	0.48934 (12)	0.0361 (5)
C2	0.9613 (2)	1.2577 (3)	0.42328 (13)	0.0415 (5)
H2A	1.0168	1.3435	0.4298	0.050*
C3	0.9398 (2)	1.1686 (3)	0.34850 (13)	0.0411 (5)
H3A	0.9795	1.1944	0.3043	0.049*
C4	0.8588 (2)	1.0407 (2)	0.33972 (12)	0.0376 (5)
C5	0.7997 (2)	1.0004 (2)	0.40428 (13)	0.0377 (5)
H5A	0.7462	0.9130	0.3971	0.045*
C6	0.81908 (19)	1.0898 (2)	0.48087 (12)	0.0325 (4)
C7	0.75211 (19)	1.0490 (2)	0.54920 (13)	0.0341 (5)
C8	0.7052 (2)	1.1213 (2)	0.68396 (12)	0.0349 (5)
C9	0.7605 (2)	1.0181 (2)	0.75146 (13)	0.0361 (5)
H9A	0.8302	0.9534	0.7471	0.043*
C10	0.71348 (19)	1.0095 (2)	0.82588 (12)	0.0343 (5)
C11	0.6078 (2)	1.1068 (2)	0.82884 (13)	0.0353 (5)
C12	0.5507 (2)	1.2078 (3)	0.76140 (14)	0.0457 (5)
H12A	0.4790	1.2703	0.7648	0.055*
C13	0.6000 (2)	1.2166 (3)	0.68838 (14)	0.0442 (5)
H13A	0.5626	1.2857	0.6429	0.053*
C14	0.6714 (2)	0.9042 (2)	0.53932 (15)	0.0497 (6)
H14A	0.6292	0.8973	0.5862	0.075*
H14B	0.7311	0.8186	0.5426	0.075*
H14C	0.6022	0.9040	0.4828	0.075*
H1O1	0.875 (3)	1.280 (3)	0.5918 (17)	0.090 (10)*
H1N2	0.845 (3)	0.875 (3)	0.8945 (15)	0.056 (8)*
H2N2	0.760 (3)	0.933 (3)	0.9416 (18)	0.068 (9)*

	U11	U22	U33	U12	U13	U23
Br1	0.0789 (2)	0.0630 (2)	0.04600 (15)	0.00123 (13)	0.03142 (13)	−0.01291 (12)
Cl1	0.0612 (4)	0.0630 (4)	0.0472 (3)	0.0015 (3)	0.0328 (3)	−0.0020 (3)
O1	0.0632 (10)	0.0497 (10)	0.0423 (9)	−0.0224 (8)	0.0241 (8)	−0.0097 (7)
N1	0.0511 (11)	0.0378 (10)	0.0321 (9)	−0.0088 (8)	0.0180 (8)	−0.0014 (8)
N2	0.0585 (14)	0.0534 (14)	0.0435 (12)	0.0162 (11)	0.0222 (11)	0.0160 (10)
C1	0.0383 (11)	0.0381 (13)	0.0314 (10)	−0.0005 (9)	0.0095 (9)	0.0032 (9)
C2	0.0408 (12)	0.0428 (13)	0.0425 (12)	−0.0045 (10)	0.0149 (10)	0.0046 (10)
C3	0.0418 (12)	0.0469 (14)	0.0400 (11)	0.0060 (11)	0.0206 (10)	0.0106 (10)
C4	0.0426 (11)	0.0396 (13)	0.0320 (10)	0.0090 (10)	0.0131 (9)	0.0022 (9)
C5	0.0435 (12)	0.0327 (12)	0.0391 (11)	0.0000 (10)	0.0157 (10)	0.0005 (9)
C6	0.0348 (10)	0.0327 (12)	0.0306 (10)	0.0014 (9)	0.0106 (8)	0.0037 (9)
C7	0.0378 (11)	0.0323 (12)	0.0328 (10)	−0.0004 (9)	0.0113 (9)	0.0033 (9)
C8	0.0420 (11)	0.0335 (12)	0.0303 (10)	−0.0072 (9)	0.0123 (9)	−0.0034 (9)
C9	0.0398 (11)	0.0340 (12)	0.0381 (11)	0.0030 (9)	0.0169 (9)	−0.0008 (9)
C10	0.0388 (11)	0.0318 (12)	0.0317 (10)	−0.0037 (9)	0.0094 (9)	0.0002 (9)
C11	0.0401 (11)	0.0370 (12)	0.0329 (10)	−0.0029 (9)	0.0173 (9)	−0.0036 (9)
C12	0.0457 (12)	0.0461 (14)	0.0489 (13)	0.0087 (11)	0.0195 (11)	0.0025 (11)
C13	0.0499 (13)	0.0445 (14)	0.0377 (11)	0.0061 (11)	0.0121 (10)	0.0082 (10)
C14	0.0631 (15)	0.0461 (15)	0.0480 (13)	−0.0175 (11)	0.0288 (11)	−0.0101 (11)

Br1—C4	1.900 (2)	C5—C6	1.401 (3)
Cl1—C11	1.7458 (18)	C5—H5A	0.9300
O1—C1	1.348 (2)	C6—C7	1.478 (2)
O1—H1O1	0.86 (3)	C7—C14	1.498 (3)
N1—C7	1.282 (2)	C8—C13	1.382 (3)
N1—C8	1.431 (2)	C8—C9	1.383 (3)
N2—C10	1.384 (3)	C9—C10	1.392 (2)
N2—H1N2	0.82 (3)	C9—H9A	0.9300
N2—H2N2	0.82 (3)	C10—C11	1.390 (3)
C1—C2	1.392 (3)	C11—C12	1.373 (3)
C1—C6	1.409 (3)	C12—C13	1.385 (3)
C2—C3	1.374 (3)	C12—H12A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.378 (3)	C14—H14A	0.9600
C3—H3A	0.9300	C14—H14B	0.9600
C4—C5	1.372 (3)	C14—H14C	0.9600
C1—O1—H1O1	105.6 (19)	C6—C7—C14	119.31 (17)
C7—N1—C8	123.50 (17)	C13—C8—C9	120.47 (17)
C10—N2—H1N2	114.0 (17)	C13—C8—N1	118.56 (18)
C10—N2—H2N2	112.9 (18)	C9—C8—N1	120.61 (18)
H1N2—N2—H2N2	116 (2)	C8—C9—C10	120.98 (18)
O1—C1—C2	117.72 (19)	C8—C9—H9A	119.5
O1—C1—C6	122.22 (17)	C10—C9—H9A	119.5
C2—C1—C6	120.05 (19)	N2—C10—C11	121.52 (18)
C3—C2—C1	120.8 (2)	N2—C10—C9	121.06 (19)
C3—C2—H2A	119.6	C11—C10—C9	117.42 (18)
C1—C2—H2A	119.6	C12—C11—C10	121.97 (17)
C2—C3—C4	119.29 (18)	C12—C11—Cl1	119.54 (15)
C2—C3—H3A	120.4	C10—C11—Cl1	118.44 (15)
C4—C3—H3A	120.4	C11—C12—C13	119.95 (19)
C5—C4—C3	121.26 (19)	C11—C12—H12A	120.0
C5—C4—Br1	119.84 (16)	C13—C12—H12A	120.0
C3—C4—Br1	118.87 (14)	C8—C13—C12	119.2 (2)
C4—C5—C6	120.66 (19)	C8—C13—H13A	120.4
C4—C5—H5A	119.7	C12—C13—H13A	120.4
C6—C5—H5A	119.7	C7—C14—H14A	109.5
C5—C6—C1	117.94 (17)	C7—C14—H14B	109.5
C5—C6—C7	120.68 (18)	H14A—C14—H14B	109.5
C1—C6—C7	121.36 (17)	C7—C14—H14C	109.5
N1—C7—C6	116.84 (17)	H14A—C14—H14C	109.5
N1—C7—C14	123.84 (17)	H14B—C14—H14C	109.5
O1—C1—C2—C3	−177.75 (18)	C5—C6—C7—C14	4.6 (3)
C6—C1—C2—C3	1.2 (3)	C1—C6—C7—C14	−177.06 (19)
C1—C2—C3—C4	−0.8 (3)	C7—N1—C8—C13	−110.9 (2)
C2—C3—C4—C5	−0.2 (3)	C7—N1—C8—C9	76.0 (3)
C2—C3—C4—Br1	177.57 (15)	C13—C8—C9—C10	−1.2 (3)
C3—C4—C5—C6	0.6 (3)	N1—C8—C9—C10	171.82 (18)
Br1—C4—C5—C6	−177.08 (14)	C8—C9—C10—N2	−180.0 (2)
C4—C5—C6—C1	−0.2 (3)	C8—C9—C10—C11	1.0 (3)
C4—C5—C6—C7	178.20 (18)	N2—C10—C11—C12	−178.9 (2)
O1—C1—C6—C5	178.19 (18)	C9—C10—C11—C12	0.2 (3)
C2—C1—C6—C5	−0.7 (3)	N2—C10—C11—Cl1	3.7 (3)
O1—C1—C6—C7	−0.2 (3)	C9—C10—C11—Cl1	−177.24 (15)
C2—C1—C6—C7	−179.09 (18)	C10—C11—C12—C13	−1.1 (3)
C8—N1—C7—C6	179.02 (17)	Cl1—C11—C12—C13	176.27 (17)
C8—N1—C7—C14	0.2 (3)	C9—C8—C13—C12	0.2 (3)
C5—C6—C7—N1	−174.25 (18)	N1—C8—C13—C12	−172.91 (19)
C1—C6—C7—N1	4.1 (3)	C11—C12—C13—C8	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.86 (3)	1.74 (3)	2.533 (2)	151 (3)
N2—H1N2···O1i	0.82 (3)	2.33 (3)	3.129 (3)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.86 (3)	1.74 (3)	2.533 (2)	151 (3)
N2—H1N2⋯O1i	0.82 (3)	2.33 (3)	3.129 (3)	163 (2)

Symmetry code: (i) .