2-Benzyl-imino-meth-yl-6-bromo-4-chloro-phenol.

The title mol-ecule, C(14)H(11)BrClNO, adopts a trans configuration with respect to the C=N double bond. The dihedral angle between the two aromatic rings is 70.4 (5)°. An intra-molecular O-H⋯N hydrogen bond is observed between the hydroxyl and imine groups.

Related literature

For related literature, see: Ali et al. (2002 ▶); Cukurovali et al. (2002 ▶); Tarafder et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H11BrClNO

M = 324.60

Monoclinic,

a = 4.3334 (8) Å

b = 12.8976 (14) Å

c = 23.892 (2) Å

β = 92.992 (1)°

V = 1333.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.27 mm−1

T = 298 (2) K

0.40 × 0.37 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.355, T max = 0.676

6753 measured reflections

2325 independent reflections

1699 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.176

S = 1.06

2325 reflections

163 parameters

H-atom parameters constrained

Δρmax = 1.47 e Å−3

Δρmin = −0.76 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024884/ci2649sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024884/ci2649Isup2.hkl

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

Enhanced figure: interactive version of Fig. 1

C14H11BrClNO	F000 = 648
Mr = 324.60	Dx = 1.617 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2314 reflections
a = 4.3334 (8) Å	θ = 3.0–23.6º
b = 12.8976 (14) Å	µ = 3.27 mm−1
c = 23.892 (2) Å	T = 298 (2) K
β = 92.992 (1)º	Block, yellow
V = 1333.5 (3) Å3	0.40 × 0.37 × 0.13 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2325 independent reflections
Radiation source: fine-focus sealed tube	1699 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.068
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.355, Tmax = 0.676	k = −14→15
6753 measured reflections	l = −28→19

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.176	w = 1/[σ2(Fo2) + (0.0638P)2 + 4.7838P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2325 reflections	Δρmax = 1.47 e Å−3
163 parameters	Δρmin = −0.76 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	1.1330 (2)	0.05445 (6)	0.34840 (4)	0.0688 (3)
Cl1	1.1495 (6)	0.47661 (15)	0.37758 (10)	0.0761 (6)
N1	0.4056 (13)	0.2399 (4)	0.1816 (2)	0.0495 (14)
O1	0.7218 (12)	0.1150 (3)	0.2472 (2)	0.0588 (13)
H1	0.6061	0.1323	0.2205	0.088*
C1	0.4902 (15)	0.3140 (6)	0.2137 (3)	0.0465 (16)
H1A	0.4104	0.3798	0.2062	0.056*
C2	0.7087 (14)	0.3002 (5)	0.2620 (3)	0.0409 (14)
C3	0.8091 (15)	0.1982 (5)	0.2763 (3)	0.0419 (15)
C4	1.0094 (15)	0.1881 (5)	0.3238 (3)	0.0442 (15)
C5	1.1108 (15)	0.2704 (5)	0.3547 (3)	0.0425 (15)
H5	1.2421	0.2609	0.3864	0.051*
C6	1.0135 (16)	0.3711 (5)	0.3381 (3)	0.0476 (16)
C7	0.8123 (16)	0.3849 (5)	0.2934 (3)	0.0481 (16)
H7	0.7434	0.4511	0.2839	0.058*
C8	0.1902 (16)	0.2605 (6)	0.1331 (3)	0.0562 (19)
H8A	0.0875	0.3264	0.1380	0.067*
H8B	0.0339	0.2066	0.1302	0.067*
C9	0.3671 (15)	0.2630 (6)	0.0799 (3)	0.0480 (17)
C10	0.4684 (18)	0.3549 (7)	0.0600 (3)	0.066 (2)
H10	0.4266	0.4163	0.0786	0.080*
C11	0.635 (2)	0.3571 (9)	0.0117 (4)	0.082 (3)
H11	0.7064	0.4196	−0.0021	0.099*
C12	0.691 (2)	0.2664 (10)	−0.0149 (4)	0.086 (3)
H12	0.8006	0.2675	−0.0473	0.103*
C13	0.594 (2)	0.1762 (9)	0.0043 (4)	0.084 (3)
H13	0.6386	0.1154	−0.0146	0.101*
C14	0.4270 (18)	0.1718 (7)	0.0517 (4)	0.069 (2)
H14	0.3557	0.1087	0.0646	0.083*

	U11	U22	U33	U12	U13	U23
Br1	0.0795 (6)	0.0510 (5)	0.0758 (6)	0.0131 (4)	0.0027 (4)	0.0117 (4)
Cl1	0.0979 (16)	0.0525 (11)	0.0767 (14)	−0.0047 (10)	−0.0060 (12)	−0.0098 (10)
N1	0.039 (3)	0.066 (4)	0.044 (3)	0.000 (3)	0.003 (3)	0.003 (3)
O1	0.076 (3)	0.047 (3)	0.053 (3)	0.000 (2)	0.001 (2)	−0.002 (2)
C1	0.039 (4)	0.056 (4)	0.045 (4)	0.002 (3)	0.013 (3)	0.009 (3)
C2	0.039 (3)	0.046 (3)	0.040 (4)	−0.001 (3)	0.016 (3)	0.001 (3)
C3	0.042 (4)	0.042 (3)	0.043 (4)	−0.001 (3)	0.016 (3)	0.001 (3)
C4	0.040 (4)	0.049 (4)	0.045 (4)	0.004 (3)	0.019 (3)	0.008 (3)
C5	0.042 (4)	0.047 (3)	0.039 (4)	0.002 (3)	0.008 (3)	0.001 (3)
C6	0.049 (4)	0.048 (4)	0.046 (4)	−0.001 (3)	0.009 (3)	−0.003 (3)
C7	0.053 (4)	0.042 (3)	0.050 (4)	0.005 (3)	0.011 (3)	0.000 (3)
C8	0.035 (4)	0.078 (5)	0.055 (5)	0.000 (3)	−0.002 (3)	0.001 (4)
C9	0.037 (4)	0.068 (4)	0.038 (4)	0.002 (3)	−0.007 (3)	0.002 (3)
C10	0.052 (5)	0.082 (6)	0.065 (5)	0.000 (4)	−0.002 (4)	0.007 (4)
C11	0.059 (5)	0.115 (8)	0.072 (6)	0.000 (5)	−0.003 (5)	0.028 (6)
C12	0.062 (6)	0.144 (10)	0.051 (6)	0.013 (6)	0.005 (4)	0.006 (6)
C13	0.068 (6)	0.113 (8)	0.070 (6)	0.022 (6)	−0.007 (5)	−0.028 (6)
C14	0.055 (5)	0.081 (6)	0.071 (6)	0.004 (4)	−0.010 (4)	−0.010 (5)

Br1—C4	1.890 (6)	C7—H7	0.93
Cl1—C6	1.741 (7)	C8—C9	1.518 (10)
N1—C1	1.267 (9)	C8—H8A	0.97
N1—C8	1.473 (9)	C8—H8B	0.97
O1—C3	1.325 (8)	C9—C10	1.359 (10)
O1—H1	0.82	C9—C14	1.386 (11)
C1—C2	1.465 (9)	C10—C11	1.392 (12)
C1—H1A	0.93	C10—H10	0.93
C2—C7	1.387 (9)	C11—C12	1.360 (14)
C2—C3	1.422 (9)	C11—H11	0.93
C3—C4	1.397 (9)	C12—C13	1.326 (14)
C4—C5	1.353 (9)	C12—H12	0.93
C5—C6	1.416 (9)	C13—C14	1.377 (13)
C5—H5	0.93	C13—H13	0.93
C6—C7	1.355 (9)	C14—H14	0.93
C1—N1—C8	119.5 (6)	N1—C8—H8A	109.7
C3—O1—H1	109.5	C9—C8—H8A	109.7
N1—C1—C2	122.7 (6)	N1—C8—H8B	109.7
N1—C1—H1A	118.7	C9—C8—H8B	109.7
C2—C1—H1A	118.7	H8A—C8—H8B	108.2
C7—C2—C3	120.7 (6)	C10—C9—C14	119.8 (8)
C7—C2—C1	120.6 (6)	C10—C9—C8	119.9 (7)
C3—C2—C1	118.7 (6)	C14—C9—C8	120.3 (7)
O1—C3—C4	120.0 (6)	C9—C10—C11	119.9 (9)
O1—C3—C2	123.2 (6)	C9—C10—H10	120.0
C4—C3—C2	116.9 (6)	C11—C10—H10	120.0
C5—C4—C3	122.7 (6)	C12—C11—C10	118.9 (10)
C5—C4—Br1	117.8 (5)	C12—C11—H11	120.6
C3—C4—Br1	119.4 (5)	C10—C11—H11	120.6
C4—C5—C6	118.9 (6)	C13—C12—C11	121.7 (10)
C4—C5—H5	120.6	C13—C12—H12	119.1
C6—C5—H5	120.6	C11—C12—H12	119.1
C7—C6—C5	120.7 (6)	C12—C13—C14	120.6 (10)
C7—C6—Cl1	120.7 (5)	C12—C13—H13	119.7
C5—C6—Cl1	118.6 (5)	C14—C13—H13	119.7
C6—C7—C2	120.1 (6)	C13—C14—C9	119.0 (9)
C6—C7—H7	120.0	C13—C14—H14	120.5
C2—C7—H7	120.0	C9—C14—H14	120.5
N1—C8—C9	109.6 (5)
C8—N1—C1—C2	−178.6 (6)	C5—C6—C7—C2	−2.7 (10)
N1—C1—C2—C7	175.2 (6)	Cl1—C6—C7—C2	179.2 (5)
N1—C1—C2—C3	−5.7 (9)	C3—C2—C7—C6	0.7 (10)
C7—C2—C3—O1	−178.8 (6)	C1—C2—C7—C6	179.8 (6)
C1—C2—C3—O1	2.1 (9)	C1—N1—C8—C9	102.8 (7)
C7—C2—C3—C4	1.2 (9)	N1—C8—C9—C10	−94.4 (8)
C1—C2—C3—C4	−177.9 (5)	N1—C8—C9—C14	85.3 (8)
O1—C3—C4—C5	178.9 (6)	C14—C9—C10—C11	−0.7 (11)
C2—C3—C4—C5	−1.1 (9)	C8—C9—C10—C11	179.0 (6)
O1—C3—C4—Br1	−3.9 (8)	C9—C10—C11—C12	0.4 (12)
C2—C3—C4—Br1	176.1 (4)	C10—C11—C12—C13	−0.6 (14)
C3—C4—C5—C6	−0.8 (9)	C11—C12—C13—C14	1.0 (14)
Br1—C4—C5—C6	−178.1 (5)	C12—C13—C14—C9	−1.2 (13)
C4—C5—C6—C7	2.7 (10)	C10—C9—C14—C13	1.1 (11)
C4—C5—C6—Cl1	−179.1 (5)	C8—C9—C14—C13	−178.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.590 (7)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.590 (7)	147