2-Bromo-4-chloro-6-(cyclo-pentyl-imino-meth-yl)phenol.

All atoms of the title mol-ecule, C(12)H(13)BrClNO, except the C and H atoms of the cyclo-pentane methyl-ene groups lie on a crystallographic mirror plane. The cyclo-pentane ring adopts an envelope conformation and an intra-molecular O-H⋯N hydrogen bond is observed. In the crystal, mol-ecules are stacked along the b axis by π-π inter-actions [centroid-centroid distance = 3.6424 (11) Å].

Related literature

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000 ▶); Sriram et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For the coordination chemistry of Schiff bases, see: Ali et al. (2008 ▶); Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For the crystal structures of Schiff base compounds, see: Fun et al. (2009 ▶); Nadeem et al. (2009 ▶); Eltayeb et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H13BrClNO

M = 302.59

Orthorhombic,

a = 12.142 (2) Å

b = 6.8610 (14) Å

c = 15.077 (3) Å

V = 1256.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.46 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.544, T max = 0.574

10340 measured reflections

1488 independent reflections

1132 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.08

1488 reflections

93 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.89 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039142/ci2924sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039142/ci2924Isup2.hkl

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

C12H13BrClNO	F(000) = 608
Mr = 302.59	Dx = 1.600 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2255 reflections
a = 12.142 (2) Å	θ = 2.6–24.5°
b = 6.8610 (14) Å	µ = 3.46 mm−1
c = 15.077 (3) Å	T = 298 K
V = 1256.0 (4) Å3	Block, yellow
Z = 4	0.20 × 0.20 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	1488 independent reflections
Radiation source: fine-focus sealed tube	1132 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.544, Tmax = 0.574	k = −8→8
10340 measured reflections	l = −19→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0628P)2 + 0.5702P] where P = (Fo2 + 2Fc2)/3
1488 reflections	(Δ/σ)max = 0.001
93 parameters	Δρmax = 0.40 e Å−3
6 restraints	Δρmin = −0.89 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
Br1	−0.24144 (4)	0.2500	0.43777 (4)	0.0689 (3)
Cl1	0.17429 (13)	0.2500	0.29606 (9)	0.0784 (5)
O1	−0.1127 (2)	0.2500	0.60853 (19)	0.0495 (7)
H1	−0.063 (5)	0.2500	0.652 (4)	0.074*
N1	0.0610 (3)	0.2500	0.7067 (2)	0.0529 (9)
C1	0.0712 (3)	0.2500	0.5489 (3)	0.0411 (9)
C2	−0.0460 (3)	0.2500	0.5392 (3)	0.0401 (9)
C3	−0.0878 (4)	0.2500	0.4537 (3)	0.0428 (9)
C4	−0.0210 (4)	0.2500	0.3801 (3)	0.0510 (11)
H4	−0.0517	0.2500	0.3235	0.061*
C5	0.0921 (4)	0.2500	0.3908 (3)	0.0515 (11)
C6	0.1374 (4)	0.2500	0.4740 (3)	0.0498 (10)
H6	0.2136	0.2500	0.4804	0.060*
C7	0.1190 (4)	0.2500	0.6365 (3)	0.0506 (10)
H7	0.1953	0.2500	0.6418	0.061*
C8	0.1145 (4)	0.2500	0.7942 (3)	0.0627 (14)
H8	0.1950	0.2500	0.7893	0.075*
C9	0.0723 (4)	0.0775 (6)	0.8482 (3)	0.0887 (14)
H9A	0.0620	−0.0359	0.8107	0.106*
H9B	0.1237	0.0447	0.8952	0.106*
C10	−0.0323 (5)	0.1421 (10)	0.8850 (4)	0.133 (2)
H10A	−0.0409	0.0934	0.9450	0.159*
H10B	−0.0928	0.0934	0.8493	0.159*

	U11	U22	U33	U12	U13	U23
Br1	0.0544 (3)	0.0935 (5)	0.0588 (4)	0.000	−0.0150 (2)	0.000
Cl1	0.0888 (10)	0.0947 (11)	0.0517 (7)	0.000	0.0307 (7)	0.000
O1	0.0437 (16)	0.0639 (19)	0.0409 (16)	0.000	0.0048 (13)	0.000
N1	0.048 (2)	0.072 (3)	0.0388 (19)	0.000	−0.0052 (16)	0.000
C1	0.041 (2)	0.040 (2)	0.042 (2)	0.000	−0.0002 (16)	0.000
C2	0.049 (2)	0.032 (2)	0.039 (2)	0.000	0.0013 (17)	0.000
C3	0.051 (2)	0.035 (2)	0.042 (2)	0.000	−0.0035 (18)	0.000
C4	0.075 (3)	0.043 (2)	0.036 (2)	0.000	0.001 (2)	0.000
C5	0.063 (3)	0.049 (3)	0.042 (2)	0.000	0.015 (2)	0.000
C6	0.046 (2)	0.049 (2)	0.054 (3)	0.000	0.012 (2)	0.000
C7	0.041 (2)	0.061 (3)	0.051 (2)	0.000	−0.0026 (19)	0.000
C8	0.043 (2)	0.100 (4)	0.046 (2)	0.000	−0.010 (2)	0.000
C9	0.134 (4)	0.076 (3)	0.057 (2)	0.008 (3)	−0.034 (2)	0.007 (2)
C10	0.108 (4)	0.180 (6)	0.110 (4)	−0.023 (4)	0.015 (3)	0.040 (4)

Br1—C3	1.881 (5)	C5—C6	1.370 (6)
Cl1—C5	1.743 (4)	C6—H6	0.93
O1—C2	1.322 (5)	C7—H7	0.93
O1—H1	0.89 (6)	C8—C9	1.526 (5)
N1—C7	1.271 (6)	C8—C9i	1.526 (5)
N1—C8	1.470 (5)	C8—H8	0.98
C1—C6	1.385 (6)	C9—C10	1.455 (7)
C1—C2	1.430 (6)	C9—H9A	0.97
C1—C7	1.443 (6)	C9—H9B	0.97
C2—C3	1.386 (6)	C10—C10i	1.480 (14)
C3—C4	1.374 (6)	C10—H10A	0.97
C4—C5	1.383 (7)	C10—H10B	0.97
C4—H4	0.93
C2—O1—H1	99 (4)	N1—C7—H7	118.7
C7—N1—C8	120.1 (4)	C1—C7—H7	118.7
C6—C1—C2	119.6 (4)	N1—C8—C9	109.3 (3)
C6—C1—C7	120.8 (4)	N1—C8—C9i	109.3 (3)
C2—C1—C7	119.5 (4)	C9—C8—C9i	101.7 (5)
O1—C2—C3	120.7 (4)	N1—C8—H8	112.0
O1—C2—C1	121.9 (4)	C9—C8—H8	112.0
C3—C2—C1	117.3 (4)	C9i—C8—H8	112.0
C4—C3—C2	122.3 (4)	C10—C9—C8	105.1 (4)
C4—C3—Br1	118.9 (3)	C10—C9—H9A	110.7
C2—C3—Br1	118.8 (3)	C8—C9—H9A	110.7
C3—C4—C5	119.4 (4)	C10—C9—H9B	110.7
C3—C4—H4	120.3	C8—C9—H9B	110.7
C5—C4—H4	120.3	H9A—C9—H9B	108.8
C6—C5—C4	120.4 (4)	C9—C10—C10i	107.7 (3)
C6—C5—Cl1	121.4 (4)	C9—C10—H10A	110.2
C4—C5—Cl1	118.2 (3)	C10i—C10—H10A	110.2
C5—C6—C1	120.8 (4)	C9—C10—H10B	110.2
C5—C6—H6	119.6	C10i—C10—H10B	110.2
C1—C6—H6	119.6	H10A—C10—H10B	108.5
N1—C7—C1	122.7 (4)
C6—C1—C2—O1	180.0	C4—C5—C6—C1	0.0
C7—C1—C2—O1	0.0	Cl1—C5—C6—C1	180.0
C6—C1—C2—C3	0.0	C2—C1—C6—C5	0.0
C7—C1—C2—C3	180.0	C7—C1—C6—C5	180.0
O1—C2—C3—C4	180.0	C8—N1—C7—C1	180.0
C1—C2—C3—C4	0.0	C6—C1—C7—N1	180.0
O1—C2—C3—Br1	0.0	C2—C1—C7—N1	0.000 (1)
C1—C2—C3—Br1	180.0	C7—N1—C8—C9	−124.7 (3)
C2—C3—C4—C5	0.0	C7—N1—C8—C9i	124.7 (3)
Br1—C3—C4—C5	180.0	N1—C8—C9—C10	−81.8 (4)
C3—C4—C5—C6	0.0	C9i—C8—C9—C10	33.7 (5)
C3—C4—C5—Cl1	180.0	C8—C9—C10—C10i	−21.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.89 (6)	1.71 (6)	2.577 (5)	162 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.89 (6)	1.71 (6)	2.577 (5)	162 (5)