2-Bromo-4-chloro-6-(4-fluoro-phenyl-imino-meth-yl)phenol.

The two mol-ecules of the title compound, C(13)H(8)BrClFNO, in the asymmetric unit are inter-connected by π-π inter-actions between the salicylaldehyde and aniline units, the shortest inter-planar distance being 3.317 (3) Å. These pairs and their translation equivalents are further linked by C-H⋯F hydrogen bonds, forming a one-dimensional infinite chain. In addition, there is an intra-molecular O-H⋯N hydrogen bond connecting the OH group and the imine N atom.

Related literature

For related literature, see: Collinson & Fenton (1996 ▶); Garnovski & Vasil Chenko (2002 ▶); Kannan & Ramesh (2006 ▶); Karvembu et al. (2003 ▶); Kumar & Ramesh (2004 ▶); Nakajima et al. (1998 ▶); Prabhakaran et al. (2004 ▶); Ramesh & Maheswaran (2003 ▶); Sivagamasundari & Ramesh (2007 ▶).

Experimental

Crystal data

C13H8BrClFNO

M = 328.56

Triclinic,

a = 8.2274 (3) Å

b = 8.6566 (3) Å

c = 10.8880 (4) Å

α = 69.545 (2)°

β = 70.820 (2)°

γ = 62.341 (2)°

V = 630.48 (4) Å3

Z = 2

Mo Kα radiation

μ = 3.47 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEX2 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.451, T max = 0.573 (expected range = 0.393–0.500)

16111 measured reflections

3975 independent reflections

2533 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.138

S = 0.99

3975 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017443/im2067sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017443/im2067Isup2.hkl

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

C13H8BrClFNO	Z = 2
Mr = 328.56	F000 = 324
Triclinic, P1	Dx = 1.731 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.2274 (3) Å	Cell parameters from 5635 reflections
b = 8.6566 (3) Å	θ = 2.7–31.1º
c = 10.8880 (4) Å	µ = 3.47 mm−1
α = 69.545 (2)º	T = 293 (2) K
β = 70.820 (2)º	Rectangle, pale orange
γ = 62.341 (2)º	0.30 × 0.20 × 0.20 mm
V = 630.48 (4) Å3

Bruker APEX2 CCD diffractometer	3975 independent reflections
Radiation source: fine-focus sealed tube	2533 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 293(2) K	θmax = 30.9º
ω and φ scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −11→11
Tmin = 0.451, Tmax = 0.573	k = −12→12
16111 measured reflections	l = −15→15

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0708P)2 + 0.3467P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3975 reflections	Δρmax = 0.72 e Å−3
164 parameters	Δρmin = −0.56 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
C1	0.3576 (4)	0.9290 (4)	0.1434 (3)	0.0520 (7)
C2	0.3513 (4)	1.0070 (4)	0.2347 (3)	0.0572 (7)
H2	0.2789	1.1284	0.2308	0.069*
C3	0.4551 (4)	0.9013 (4)	0.3333 (3)	0.0501 (6)
H3	0.4523	0.9521	0.3968	0.060*
C4	0.5627 (3)	0.7212 (3)	0.3389 (2)	0.0384 (5)
C5	0.5679 (4)	0.6469 (4)	0.2429 (3)	0.0486 (6)
H5	0.6412	0.5261	0.2448	0.058*
C6	0.4637 (4)	0.7527 (4)	0.1440 (3)	0.0535 (7)
H6	0.4662	0.7040	0.0792	0.064*
C7	0.7801 (4)	0.4644 (3)	0.4552 (3)	0.0405 (5)
H7	0.8117	0.4086	0.3866	0.049*
C8	0.8715 (3)	0.3665 (3)	0.5699 (2)	0.0366 (5)
C9	0.8321 (3)	0.4496 (3)	0.6718 (3)	0.0378 (5)
C10	0.9237 (4)	0.3494 (3)	0.7792 (3)	0.0417 (5)
C11	1.0468 (4)	0.1735 (3)	0.7878 (3)	0.0433 (6)
H11	1.1053	0.1086	0.8607	0.052*
C12	1.0820 (4)	0.0950 (3)	0.6861 (3)	0.0434 (6)
C13	0.9977 (4)	0.1888 (3)	0.5779 (3)	0.0427 (5)
H13	1.0248	0.1338	0.5098	0.051*
N1	0.6581 (3)	0.6243 (3)	0.4471 (2)	0.0402 (5)
O1	0.7120 (3)	0.6194 (2)	0.6688 (2)	0.0525 (5)
H1	0.6570	0.6571	0.6070	0.087 (13)*
F1	0.2529 (3)	1.0312 (3)	0.04826 (19)	0.0759 (6)
Cl1	1.23745 (13)	−0.12851 (9)	0.69813 (9)	0.0681 (2)
Br1	0.87756 (6)	0.45988 (5)	0.91496 (4)	0.07867 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0463 (14)	0.0613 (17)	0.0414 (14)	−0.0219 (13)	−0.0227 (12)	0.0098 (13)
C2	0.0576 (17)	0.0432 (14)	0.0585 (18)	−0.0087 (13)	−0.0269 (14)	0.0004 (13)
C3	0.0554 (16)	0.0432 (14)	0.0507 (15)	−0.0129 (12)	−0.0241 (12)	−0.0063 (12)
C4	0.0385 (12)	0.0400 (12)	0.0367 (12)	−0.0169 (10)	−0.0153 (10)	0.0002 (10)
C5	0.0505 (15)	0.0456 (14)	0.0504 (15)	−0.0129 (12)	−0.0236 (12)	−0.0079 (12)
C6	0.0586 (17)	0.0672 (19)	0.0400 (14)	−0.0264 (15)	−0.0212 (12)	−0.0057 (13)
C7	0.0443 (13)	0.0398 (12)	0.0407 (12)	−0.0146 (10)	−0.0174 (10)	−0.0078 (10)
C8	0.0373 (11)	0.0352 (11)	0.0377 (12)	−0.0126 (9)	−0.0156 (9)	−0.0040 (9)
C9	0.0362 (11)	0.0339 (11)	0.0425 (13)	−0.0089 (9)	−0.0154 (10)	−0.0080 (10)
C10	0.0437 (13)	0.0425 (13)	0.0413 (13)	−0.0127 (10)	−0.0174 (10)	−0.0102 (10)
C11	0.0449 (13)	0.0397 (12)	0.0425 (13)	−0.0128 (10)	−0.0222 (11)	0.0005 (11)
C12	0.0429 (13)	0.0310 (11)	0.0522 (15)	−0.0083 (10)	−0.0200 (11)	−0.0044 (10)
C13	0.0471 (13)	0.0347 (12)	0.0462 (14)	−0.0100 (10)	−0.0177 (11)	−0.0102 (10)
N1	0.0409 (11)	0.0395 (11)	0.0407 (11)	−0.0139 (9)	−0.0183 (9)	−0.0034 (9)
O1	0.0568 (11)	0.0372 (9)	0.0584 (12)	0.0023 (8)	−0.0302 (9)	−0.0173 (8)
F1	0.0744 (12)	0.0842 (14)	0.0574 (11)	−0.0237 (11)	−0.0444 (10)	0.0151 (10)
Cl1	0.0768 (5)	0.0338 (3)	0.0812 (6)	0.0009 (3)	−0.0358 (4)	−0.0126 (3)
Br1	0.0981 (3)	0.0702 (3)	0.0663 (3)	−0.00208 (19)	−0.0451 (2)	−0.03146 (18)

C1—F1	1.355 (3)	C7—H7	0.9300
C1—C6	1.361 (5)	C8—C13	1.391 (3)
C1—C2	1.360 (5)	C8—C9	1.399 (3)
C2—C3	1.382 (4)	C9—O1	1.334 (3)
C2—H2	0.9300	C9—C10	1.396 (3)
C3—C4	1.381 (4)	C10—C11	1.373 (4)
C3—H3	0.9300	C10—Br1	1.878 (3)
C4—C5	1.387 (4)	C11—C12	1.379 (4)
C4—N1	1.418 (3)	C11—H11	0.9300
C5—C6	1.386 (4)	C12—C13	1.370 (3)
C5—H5	0.9300	C12—Cl1	1.741 (3)
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.270 (3)	O1—H1	0.8200
C7—C8	1.460 (3)
F1—C1—C6	118.6 (3)	C13—C8—C9	120.0 (2)
F1—C1—C2	118.5 (3)	C13—C8—C7	119.4 (2)
C6—C1—C2	122.8 (2)	C9—C8—C7	120.5 (2)
C1—C2—C3	118.3 (3)	O1—C9—C10	119.7 (2)
C1—C2—H2	120.9	O1—C9—C8	122.2 (2)
C3—C2—H2	120.9	C10—C9—C8	118.1 (2)
C4—C3—C2	120.9 (3)	C11—C10—C9	122.0 (2)
C4—C3—H3	119.6	C11—C10—Br1	119.22 (18)
C2—C3—H3	119.6	C9—C10—Br1	118.82 (19)
C3—C4—C5	119.2 (2)	C10—C11—C12	118.6 (2)
C3—C4—N1	116.1 (2)	C10—C11—H11	120.7
C5—C4—N1	124.7 (2)	C12—C11—H11	120.7
C6—C5—C4	120.0 (3)	C13—C12—C11	121.5 (2)
C6—C5—H5	120.0	C13—C12—Cl1	120.1 (2)
C4—C5—H5	120.0	C11—C12—Cl1	118.38 (19)
C1—C6—C5	118.8 (3)	C12—C13—C8	119.8 (2)
C1—C6—H6	120.6	C12—C13—H13	120.1
C5—C6—H6	120.6	C8—C13—H13	120.1
N1—C7—C8	121.3 (2)	C7—N1—C4	122.7 (2)
N1—C7—H7	119.3	C9—O1—H1	109.5
C8—C7—H7	119.3
F1—C1—C2—C3	178.5 (3)	O1—C9—C10—C11	179.2 (3)
C6—C1—C2—C3	−1.0 (5)	C8—C9—C10—C11	−1.1 (4)
C1—C2—C3—C4	0.1 (5)	O1—C9—C10—Br1	−1.2 (3)
C2—C3—C4—C5	0.8 (4)	C8—C9—C10—Br1	178.50 (19)
C2—C3—C4—N1	−177.8 (3)	C9—C10—C11—C12	0.8 (4)
C3—C4—C5—C6	−0.9 (4)	Br1—C10—C11—C12	−178.8 (2)
N1—C4—C5—C6	177.6 (2)	C10—C11—C12—C13	0.3 (4)
F1—C1—C6—C5	−178.6 (3)	C10—C11—C12—Cl1	−179.7 (2)
C2—C1—C6—C5	1.0 (5)	C11—C12—C13—C8	−0.9 (4)
C4—C5—C6—C1	0.0 (4)	Cl1—C12—C13—C8	179.0 (2)
N1—C7—C8—C13	177.0 (3)	C9—C8—C13—C12	0.6 (4)
N1—C7—C8—C9	−2.6 (4)	C7—C8—C13—C12	−179.0 (2)
C13—C8—C9—O1	−179.9 (2)	C8—C7—N1—C4	−178.1 (2)
C7—C8—C9—O1	−0.3 (4)	C3—C4—N1—C7	−170.8 (3)
C13—C8—C9—C10	0.4 (4)	C5—C4—N1—C7	10.7 (4)
C7—C8—C9—C10	180.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···F1i	0.93	2.45	3.349 (4)	162
O1—H1···N1	0.82	1.86	2.577 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯F1i	0.93	2.45	3.349 (4)	162
O1—H1⋯N1	0.82	1.86	2.577 (3)	146

Symmetry code: (i) .