2-Bromo-4-chloro-6-{(E)-[4-(diethyl-amino)-phen-yl]imino-meth-yl}phenol.

In the title compound, C(17)H(18)BrClN(2)O, the dihedral angle between the aromatic rings is 3.0 (1)°. The methyl-ethanamine group assumes an extended conformation. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by C-H⋯π and π-π [centroid-centroid distances = 3.691 (1) and 3.632 (1) Å] inter-actions.

Related literature

For Schiff base compounds in coordination chemistry, see: Weber et al. (2007 ▶); Chen et al. (2008 ▶) and for their role in biological processes, see: May et al. (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Raja et al. (2008 ▶).

Experimental

Crystal data

C17H18BrClN2O

M = 381.69

Monoclinic,

a = 11.3427 (3) Å

b = 10.9204 (3) Å

c = 14.3869 (4) Å

β = 111.418 (2)°

V = 1658.99 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.64 mm−1

T = 293 K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.977

19985 measured reflections

4383 independent reflections

2797 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.00

4383 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033738/gw2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033738/gw2086Isup2.hkl

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

C17H18BrClN2O	F(000) = 776
Mr = 381.69	Dx = 1.528 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4383 reflections
a = 11.3427 (3) Å	θ = 1.9–28.9°
b = 10.9204 (3) Å	µ = 2.64 mm−1
c = 14.3869 (4) Å	T = 293 K
β = 111.418 (2)°	Block, colourless
V = 1658.99 (8) Å3	0.21 × 0.19 × 0.17 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4383 independent reflections
Radiation source: fine-focus sealed tube	2797 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 28.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→15
Tmin = 0.972, Tmax = 0.977	k = −14→14
19985 measured reflections	l = −18→19

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.3262P] where P = (Fo2 + 2Fc2)/3
4383 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.28 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
C1	−0.10155 (19)	0.32018 (18)	0.54970 (15)	0.0458 (5)
H1	−0.1023	0.2923	0.6106	0.055*
C2	−0.17812 (19)	0.41572 (19)	0.50175 (15)	0.0443 (5)
C3	−0.17718 (19)	0.45989 (18)	0.41258 (15)	0.0456 (5)
H3	−0.2285	0.5256	0.3812	0.055*
C4	−0.09947 (18)	0.40567 (19)	0.37050 (14)	0.0434 (5)
C5	−0.02201 (17)	0.30769 (18)	0.41549 (14)	0.0412 (4)
C6	−0.02323 (17)	0.26536 (17)	0.50738 (14)	0.0398 (4)
C7	0.05636 (18)	0.16390 (18)	0.55862 (15)	0.0450 (5)
H7	0.0544	0.1382	0.6197	0.054*
C8	0.20773 (17)	0.01035 (17)	0.57157 (15)	0.0393 (4)
C9	0.28861 (19)	−0.03587 (18)	0.52790 (14)	0.0443 (5)
H9	0.2875	−0.0019	0.4683	0.053*
C10	0.37053 (19)	−0.13055 (19)	0.56995 (14)	0.0457 (5)
H10	0.4238	−0.1589	0.5385	0.055*
C11	0.37521 (17)	−0.18518 (17)	0.65933 (14)	0.0393 (4)
C12	0.29288 (18)	−0.13766 (18)	0.70294 (15)	0.0446 (5)
H12	0.2933	−0.1712	0.7625	0.054*
C13	0.21127 (18)	−0.04266 (18)	0.66006 (16)	0.0441 (5)
H13	0.1577	−0.0136	0.6910	0.053*
C14	0.5476 (2)	−0.3221 (2)	0.66057 (16)	0.0530 (5)
H14A	0.5074	−0.3263	0.5885	0.064*
H14B	0.5745	−0.4042	0.6846	0.064*
C15	0.6624 (2)	−0.2420 (3)	0.6864 (2)	0.0701 (7)
H15A	0.6367	−0.1591	0.6672	0.105*
H15B	0.7150	−0.2701	0.6515	0.105*
H15C	0.7091	−0.2454	0.7570	0.105*
C16	0.4686 (2)	−0.3271 (2)	0.79959 (16)	0.0576 (6)
H16A	0.5081	−0.4072	0.8084	0.069*
H16B	0.3851	−0.3373	0.8026	0.069*
C17	0.5454 (2)	−0.2467 (3)	0.88435 (17)	0.0756 (8)
H17A	0.6295	−0.2386	0.8840	0.113*
H17B	0.5494	−0.2826	0.9463	0.113*
H17C	0.5066	−0.1674	0.8771	0.113*
N1	0.12906 (14)	0.10877 (15)	0.52225 (12)	0.0432 (4)
N2	0.45430 (15)	−0.28149 (15)	0.70127 (12)	0.0462 (4)
Cl1	−0.27823 (7)	0.48188 (6)	0.55421 (5)	0.07030 (19)
Br1	−0.09834 (3)	0.46511 (3)	0.248320 (18)	0.07298 (12)
O1	0.04963 (14)	0.25578 (15)	0.37088 (11)	0.0584 (4)
H1A	0.0942	0.2028	0.4074	0.088*

	U11	U22	U33	U12	U13	U23
C1	0.0515 (12)	0.0407 (11)	0.0471 (11)	−0.0004 (9)	0.0205 (9)	0.0027 (9)
C2	0.0473 (11)	0.0392 (11)	0.0513 (12)	0.0029 (9)	0.0238 (9)	−0.0033 (9)
C3	0.0467 (11)	0.0368 (11)	0.0504 (12)	0.0064 (9)	0.0144 (9)	0.0023 (9)
C4	0.0454 (11)	0.0435 (12)	0.0404 (10)	0.0014 (9)	0.0146 (9)	0.0028 (9)
C5	0.0361 (10)	0.0411 (11)	0.0455 (11)	−0.0008 (8)	0.0137 (8)	−0.0042 (9)
C6	0.0382 (10)	0.0325 (10)	0.0465 (11)	−0.0027 (8)	0.0127 (8)	0.0002 (9)
C7	0.0430 (11)	0.0403 (11)	0.0498 (11)	0.0003 (9)	0.0146 (9)	0.0063 (9)
C8	0.0317 (9)	0.0362 (10)	0.0446 (10)	−0.0018 (8)	0.0073 (8)	−0.0015 (8)
C9	0.0468 (11)	0.0466 (12)	0.0365 (9)	0.0018 (9)	0.0118 (8)	0.0019 (9)
C10	0.0487 (11)	0.0493 (13)	0.0397 (10)	0.0092 (9)	0.0166 (9)	−0.0005 (9)
C11	0.0366 (10)	0.0368 (10)	0.0398 (10)	0.0008 (8)	0.0082 (8)	−0.0027 (8)
C12	0.0438 (11)	0.0461 (12)	0.0444 (10)	0.0017 (9)	0.0167 (9)	0.0060 (9)
C13	0.0384 (10)	0.0451 (12)	0.0515 (11)	0.0040 (9)	0.0195 (9)	0.0028 (10)
C14	0.0579 (13)	0.0475 (13)	0.0525 (12)	0.0171 (10)	0.0189 (10)	0.0001 (10)
C15	0.0561 (14)	0.0846 (19)	0.0759 (16)	0.0073 (13)	0.0316 (13)	−0.0034 (15)
C16	0.0572 (14)	0.0560 (14)	0.0612 (14)	0.0143 (11)	0.0236 (11)	0.0179 (12)
C17	0.0747 (17)	0.103 (2)	0.0468 (13)	0.0149 (16)	0.0191 (12)	0.0031 (14)
N1	0.0349 (8)	0.0399 (9)	0.0490 (9)	0.0008 (7)	0.0085 (7)	0.0018 (8)
N2	0.0459 (9)	0.0451 (10)	0.0462 (9)	0.0102 (8)	0.0152 (8)	0.0054 (8)
Cl1	0.0855 (4)	0.0679 (4)	0.0736 (4)	0.0250 (3)	0.0482 (4)	0.0040 (3)
Br1	0.0821 (2)	0.0911 (2)	0.05317 (15)	0.02883 (15)	0.03355 (13)	0.02548 (13)
O1	0.0581 (9)	0.0646 (11)	0.0610 (9)	0.0203 (8)	0.0318 (8)	0.0094 (8)

C1—C2	1.372 (3)	C11—N2	1.371 (2)
C1—C6	1.383 (3)	C11—C12	1.401 (3)
C1—H1	0.9300	C12—C13	1.377 (3)
C2—C3	1.374 (3)	C12—H12	0.9300
C2—Cl1	1.734 (2)	C13—H13	0.9300
C3—C4	1.373 (3)	C14—N2	1.453 (3)
C3—H3	0.9300	C14—C15	1.499 (3)
C4—C5	1.386 (3)	C14—H14A	0.9700
C4—Br1	1.878 (2)	C14—H14B	0.9700
C5—O1	1.332 (2)	C15—H15A	0.9600
C5—C6	1.405 (3)	C15—H15B	0.9600
C6—C7	1.449 (3)	C15—H15C	0.9600
C7—N1	1.277 (3)	C16—N2	1.452 (3)
C7—H7	0.9300	C16—C17	1.497 (3)
C8—C9	1.383 (3)	C16—H16A	0.9700
C8—C13	1.386 (3)	C16—H16B	0.9700
C8—N1	1.412 (2)	C17—H17A	0.9600
C9—C10	1.374 (3)	C17—H17B	0.9600
C9—H9	0.9300	C17—H17C	0.9600
C10—C11	1.401 (3)	O1—H1A	0.8200
C10—H10	0.9300
C2—C1—C6	119.89 (19)	C13—C12—H12	119.1
C2—C1—H1	120.1	C11—C12—H12	119.1
C6—C1—H1	120.1	C12—C13—C8	121.03 (19)
C1—C2—C3	121.14 (19)	C12—C13—H13	119.5
C1—C2—Cl1	119.54 (16)	C8—C13—H13	119.5
C3—C2—Cl1	119.32 (16)	N2—C14—C15	114.65 (19)
C4—C3—C2	119.05 (18)	N2—C14—H14A	108.6
C4—C3—H3	120.5	C15—C14—H14A	108.6
C2—C3—H3	120.5	N2—C14—H14B	108.6
C3—C4—C5	121.78 (19)	C15—C14—H14B	108.6
C3—C4—Br1	119.25 (15)	H14A—C14—H14B	107.6
C5—C4—Br1	118.96 (15)	C14—C15—H15A	109.5
O1—C5—C4	119.85 (18)	C14—C15—H15B	109.5
O1—C5—C6	122.04 (17)	H15A—C15—H15B	109.5
C4—C5—C6	118.11 (18)	C14—C15—H15C	109.5
C1—C6—C5	120.02 (18)	H15A—C15—H15C	109.5
C1—C6—C7	119.20 (18)	H15B—C15—H15C	109.5
C5—C6—C7	120.78 (18)	N2—C16—C17	114.7 (2)
N1—C7—C6	121.83 (19)	N2—C16—H16A	108.6
N1—C7—H7	119.1	C17—C16—H16A	108.6
C6—C7—H7	119.1	N2—C16—H16B	108.6
C9—C8—C13	117.61 (18)	C17—C16—H16B	108.6
C9—C8—N1	116.88 (18)	H16A—C16—H16B	107.6
C13—C8—N1	125.51 (19)	C16—C17—H17A	109.5
C10—C9—C8	121.93 (19)	C16—C17—H17B	109.5
C10—C9—H9	119.0	H17A—C17—H17B	109.5
C8—C9—H9	119.0	C16—C17—H17C	109.5
C9—C10—C11	121.17 (19)	H17A—C17—H17C	109.5
C9—C10—H10	119.4	H17B—C17—H17C	109.5
C11—C10—H10	119.4	C7—N1—C8	122.49 (18)
N2—C11—C12	121.54 (18)	C11—N2—C16	120.96 (17)
N2—C11—C10	122.01 (18)	C11—N2—C14	120.81 (17)
C12—C11—C10	116.44 (17)	C16—N2—C14	116.70 (16)
C13—C12—C11	121.82 (19)	C5—O1—H1A	109.5
C6—C1—C2—C3	−1.1 (3)	C8—C9—C10—C11	0.3 (3)
C6—C1—C2—Cl1	178.74 (15)	C9—C10—C11—N2	178.53 (18)
C1—C2—C3—C4	1.0 (3)	C9—C10—C11—C12	−0.3 (3)
Cl1—C2—C3—C4	−178.80 (15)	N2—C11—C12—C13	−178.59 (18)
C2—C3—C4—C5	0.0 (3)	C10—C11—C12—C13	0.3 (3)
C2—C3—C4—Br1	179.70 (15)	C11—C12—C13—C8	−0.2 (3)
C3—C4—C5—O1	178.33 (19)	C9—C8—C13—C12	0.2 (3)
Br1—C4—C5—O1	−1.4 (3)	N1—C8—C13—C12	−179.17 (18)
C3—C4—C5—C6	−0.9 (3)	C6—C7—N1—C8	179.57 (17)
Br1—C4—C5—C6	179.36 (14)	C9—C8—N1—C7	−175.52 (18)
C2—C1—C6—C5	0.1 (3)	C13—C8—N1—C7	3.9 (3)
C2—C1—C6—C7	−179.53 (18)	C12—C11—N2—C16	−8.6 (3)
O1—C5—C6—C1	−178.37 (18)	C10—C11—N2—C16	172.58 (19)
C4—C5—C6—C1	0.9 (3)	C12—C11—N2—C14	−174.04 (18)
O1—C5—C6—C7	1.3 (3)	C10—C11—N2—C14	7.2 (3)
C4—C5—C6—C7	−179.49 (18)	C17—C16—N2—C11	−74.1 (2)
C1—C6—C7—N1	178.95 (18)	C17—C16—N2—C14	91.9 (2)
C5—C6—C7—N1	−0.7 (3)	C15—C14—N2—C11	76.5 (2)
C13—C8—C9—C10	−0.3 (3)	C15—C14—N2—C16	−89.5 (2)
N1—C8—C9—C10	179.17 (18)

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.86	2.588 (2)	147
C16—H16A···Cg2i	0.96	2.90	3.814 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.86	2.588 (2)	147
C16—H16A⋯Cg2i	0.96	2.90	3.814 (2)	157

Symmetry code: (i) .