2,4-Di-bromo-6-{[(5-chloro-2-methyl-phen-yl)imino]-meth-yl}phenol.

In the mol-ecular structure of the title Schiff base, C14H10Br2ClNO, the chloro-phenyl ring and di-bromo-phenol ring are almost coplanar; the dihedral angle between the planes of the two rings is 10.50 (18)°. There is an intra-molecular O-H⋯N hydrogen bond, with an O⋯N distance of 2.576 (4)Å. The crystal structure is stabilized by π-π stacking of neighbouring aromatic rings along the b-axis direction [centroid-centroid distance = 3.6896 (5) Å].

Related literature

For general background, see: Siddiqui et al. (2006 ▶); Fukuda et al. (2009 ▶); Elmali & Elerman (1998 ▶); Karakas et al. (2004 ▶); Ebrahimipour et al. (2012 ▶). For the similar Schiff base structures, see: Zhou et al. (2009 ▶); Atalay et al. (2008 ▶).

Experimental

Crystal data

C14H10Br2ClNO

M = 403.48

Monoclinic,

a = 31.603 (5) Å

b = 6.1828 (10) Å

c = 14.890 (2) Å

β = 102.594 (15)°

V = 2839.4 (8) Å3

Z = 8

Mo Kα radiation

μ = 5.89 mm−1

T = 295 K

0.38 × 0.35 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.123, T max = 0.171

5369 measured reflections

2600 independent reflections

1839 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.082

S = 1.00

2600 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (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, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017558/rk2407sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017558/rk2407Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017558/rk2407Isup3.cml

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

C14H10Br2ClNO	F(000) = 1568
Mr = 403.48	Dx = 1.888 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1332 reflections
a = 31.603 (5) Å	θ = 3.2–29.4°
b = 6.1828 (10) Å	µ = 5.89 mm−1
c = 14.890 (2) Å	T = 295 K
β = 102.594 (15)°	Block, yellow
V = 2839.4 (8) Å3	0.38 × 0.35 × 0.30 mm
Z = 8

Bruker APEXII CCD diffractometer	2600 independent reflections
Radiation source: fine-focus sealed tube	1839 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ– and ω–scans	θmax = 25.4°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −38→37
Tmin = 0.123, Tmax = 0.171	k = −7→7
5369 measured reflections	l = −12→17

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.033P)2] where P = (Fo2 + 2Fc2)/3
2600 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.032809 (16)	0.04959 (8)	0.15977 (4)	0.07156 (19)
Br2	0.214268 (14)	0.15664 (7)	0.23337 (3)	0.06296 (18)
Cl1	0.04381 (4)	1.43342 (19)	−0.16015 (9)	0.0733 (4)
O1	0.18961 (8)	0.5562 (4)	0.1191 (2)	0.0543 (7)
H1	0.1827	0.6566	0.0829	0.081*
N1	0.13813 (10)	0.8234 (4)	0.0161 (2)	0.0398 (7)
C1	0.09405 (12)	1.1128 (6)	−0.0732 (3)	0.0425 (9)
H1A	0.0687	1.0563	−0.0605	0.051*
C2	0.09307 (13)	1.2987 (6)	−0.1244 (3)	0.0446 (10)
C3	0.12950 (15)	1.3817 (7)	−0.1455 (3)	0.0525 (11)
H3	0.1281	1.5071	−0.1805	0.063*
C4	0.16871 (14)	1.2770 (6)	−0.1143 (3)	0.0511 (11)
H4	0.1936	1.3326	−0.1293	0.061*
C5	0.17164 (12)	1.0909 (6)	−0.0610 (3)	0.0417 (9)
C6	0.13395 (12)	1.0104 (6)	−0.0405 (2)	0.0371 (9)
C7	0.21455 (13)	0.9824 (7)	−0.0262 (3)	0.0567 (11)
H7A	0.2227	0.9965	0.0395	0.085*
H7B	0.2361	1.0493	−0.0535	0.085*
H7C	0.2122	0.8319	−0.0424	0.085*
C8	0.10618 (13)	0.7192 (6)	0.0326 (3)	0.0416 (9)
H8	0.0782	0.7678	0.0079	0.050*
C9	0.11218 (12)	0.5254 (5)	0.0891 (2)	0.0373 (9)
C10	0.15431 (12)	0.4507 (6)	0.1287 (2)	0.0381 (9)
C11	0.15814 (12)	0.2580 (6)	0.1790 (2)	0.0391 (9)
C12	0.12263 (13)	0.1421 (6)	0.1892 (2)	0.0433 (10)
H12	0.1260	0.0137	0.2225	0.052*
C13	0.08149 (12)	0.2177 (6)	0.1493 (3)	0.0426 (9)
C14	0.07621 (12)	0.4088 (6)	0.1011 (3)	0.0435 (10)
H14	0.0485	0.4603	0.0764	0.052*

	U11	U22	U33	U12	U13	U23
Br1	0.0586 (3)	0.0699 (3)	0.0919 (4)	−0.0168 (2)	0.0287 (3)	0.0172 (3)
Br2	0.0527 (3)	0.0652 (3)	0.0679 (3)	0.0080 (2)	0.0066 (2)	0.0210 (2)
Cl1	0.0641 (8)	0.0718 (8)	0.0766 (9)	0.0211 (6)	−0.0010 (6)	0.0219 (6)
O1	0.0407 (16)	0.0495 (17)	0.070 (2)	−0.0082 (13)	0.0062 (14)	0.0174 (14)
N1	0.0429 (19)	0.0362 (17)	0.0400 (19)	−0.0028 (15)	0.0082 (15)	0.0012 (15)
C1	0.040 (2)	0.039 (2)	0.047 (2)	−0.0042 (18)	0.0064 (19)	0.0021 (19)
C2	0.048 (2)	0.043 (2)	0.039 (2)	0.0113 (19)	0.0019 (19)	0.0023 (19)
C3	0.070 (3)	0.043 (2)	0.043 (3)	0.001 (2)	0.010 (2)	0.0080 (19)
C4	0.055 (3)	0.055 (3)	0.046 (3)	−0.009 (2)	0.017 (2)	0.005 (2)
C5	0.047 (2)	0.041 (2)	0.037 (2)	−0.0023 (18)	0.0093 (19)	0.0002 (18)
C6	0.045 (2)	0.031 (2)	0.035 (2)	−0.0017 (17)	0.0076 (18)	−0.0045 (16)
C7	0.044 (2)	0.071 (3)	0.056 (3)	−0.002 (2)	0.013 (2)	0.013 (2)
C8	0.038 (2)	0.037 (2)	0.050 (2)	0.0060 (18)	0.0096 (19)	0.0013 (18)
C9	0.042 (2)	0.034 (2)	0.038 (2)	−0.0011 (17)	0.0124 (18)	−0.0015 (17)
C10	0.044 (2)	0.034 (2)	0.038 (2)	−0.0053 (18)	0.0106 (18)	−0.0038 (17)
C11	0.043 (2)	0.037 (2)	0.037 (2)	0.0001 (17)	0.0105 (18)	0.0001 (18)
C12	0.061 (3)	0.035 (2)	0.038 (2)	0.0003 (19)	0.019 (2)	0.0013 (17)
C13	0.042 (2)	0.045 (2)	0.042 (2)	−0.0095 (19)	0.0130 (19)	−0.0016 (19)
C14	0.040 (2)	0.043 (2)	0.050 (2)	0.0046 (18)	0.0132 (19)	0.0041 (19)

Br1—C13	1.891 (4)	C5—C6	1.385 (5)
Br2—C11	1.889 (4)	C5—C7	1.500 (5)
Cl1—C2	1.744 (4)	C7—H7A	0.9600
O1—C10	1.327 (4)	C7—H7B	0.9600
O1—H1	0.8200	C7—H7C	0.9600
N1—C8	1.266 (4)	C8—C9	1.453 (5)
N1—C6	1.420 (4)	C8—H8	0.9300
C1—C2	1.376 (5)	C9—C14	1.390 (5)
C1—C6	1.400 (5)	C9—C10	1.411 (5)
C1—H1A	0.9300	C10—C11	1.398 (5)
C2—C3	1.358 (6)	C11—C12	1.367 (5)
C3—C4	1.385 (6)	C12—C13	1.387 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.389 (5)	C13—C14	1.373 (5)
C4—H4	0.9300	C14—H14	0.9300
C10—O1—H1	109.5	H7A—C7—H7C	109.5
C8—N1—C6	123.7 (3)	H7B—C7—H7C	109.5
C2—C1—C6	118.7 (4)	N1—C8—C9	121.5 (3)
C2—C1—H1A	120.7	N1—C8—H8	119.2
C6—C1—H1A	120.7	C9—C8—H8	119.2
C3—C2—C1	121.8 (4)	C14—C9—C10	120.0 (3)
C3—C2—Cl1	119.6 (3)	C14—C9—C8	119.7 (3)
C1—C2—Cl1	118.6 (3)	C10—C9—C8	120.3 (3)
C2—C3—C4	119.1 (4)	O1—C10—C11	120.0 (3)
C2—C3—H3	120.4	O1—C10—C9	122.2 (3)
C4—C3—H3	120.4	C11—C10—C9	117.8 (3)
C3—C4—C5	121.5 (4)	C12—C11—C10	121.9 (3)
C3—C4—H4	119.3	C12—C11—Br2	119.7 (3)
C5—C4—H4	119.3	C10—C11—Br2	118.4 (3)
C6—C5—C4	118.0 (3)	C11—C12—C13	119.4 (3)
C6—C5—C7	121.3 (3)	C11—C12—H12	120.3
C4—C5—C7	120.7 (4)	C13—C12—H12	120.3
C5—C6—C1	120.9 (3)	C14—C13—C12	120.6 (3)
C5—C6—N1	116.8 (3)	C14—C13—Br1	120.5 (3)
C1—C6—N1	122.3 (3)	C12—C13—Br1	118.9 (3)
C5—C7—H7A	109.5	C13—C14—C9	120.3 (3)
C5—C7—H7B	109.5	C13—C14—H14	119.9
H7A—C7—H7B	109.5	C9—C14—H14	119.9
C5—C7—H7C	109.5
C9—C8—N1—C6	178.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.576 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.576 (4)	147