2-[(4-Bromo-benzyl-idene)amino]-ethanol.

In the crystal structure of the title compound, C9H10BrNO, molecules are linked via O-H⋯N hydrogen bonds of a moderate strength between the hy-droxy groups and the imine N atoms. These hydrogen bonds, as well as the planes of the bromo-phenyl rings, are situated in alternating planes parallel to (013) and (0-13). In addition, there are weak C-H⋯π inter-actions in the structure.

Related literature

For previous work on the preparation of imine-based ligands, by our group, see: Williams et al. (2007 ▶). For related structures and their preparation, see: Elslager et al. (1956 ▶); Vennila et al. (2010 ▶); Jafarpour et al. (2011 ▶). For n class="Chemical">imines, see: Morrison et al. (1987 ▶); Tidwell (2007 ▶) and for their biological activity, see: Solomon & Lowery (1993 ▶); Fioravanti et al. (1995 ▶); Mallikarjun & Sangamesh (1997 ▶); Samadhiya & Halve (2001 ▶); Gerdemann et al. (2002 ▶); Veverková & Toma (2008 ▶); Khan et al. (2009 ▶). For classification of hydrogen bonds, see: Gilli & Gilli (2009 ▶).

Experimental

Crystal data

C9H10BrNO

M = 228.09

Monoclinic,

a = 22.349 (4) Å

b = 6.0328 (10) Å

c = 7.3673 (12) Å

β = 107.980 (3)°

V = 944.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.30 mm−1

T = 173 K

0.36 × 0.15 × 0.02 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.305, T max = 0.919

3713 measured reflections

1651 independent reflections

1550 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.059

S = 1.00

1651 reflections

113 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.71 e Å−3

Δρmin = −0.45 e Å−3

Absolute structure: Flack (1983 ▶), 788 Friedel pairs

Flack parameter: 0.022 (12)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (n class="Chemical">Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048155/fb2276sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048155/fb2276Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048155/fb2276Isup3.cml

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

C9H10BrNO	F(000) = 456
Mr = 228.09	Dx = 1.604 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3713 reflections
a = 22.349 (4) Å	θ = 3.5–25.3°
b = 6.0328 (10) Å	µ = 4.30 mm−1
c = 7.3673 (12) Å	T = 173 K
β = 107.980 (3)°	Plate, colourless
V = 944.8 (3) Å3	0.36 × 0.15 × 0.02 mm
Z = 4

Bruker Kappa DUO APEXII diffractometer	1651 independent reflections
Radiation source: fine-focus sealed tube	1550 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
0.5° φ scans and ω scans	θmax = 25.3°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −24→26
Tmin = 0.305, Tmax = 0.919	k = −7→7
3713 measured reflections	l = −8→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0174P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1651 reflections	Δρmax = 0.71 e Å−3
113 parameters	Δρmin = −0.45 e Å−3
1 restraint	Absolute structure: Flack (1983), 788 Friedel pairs
37 constraints	Flack parameter: 0.022 (12)
Primary atom site location: structure-invariant direct methods

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	0.682260 (18)	0.64650 (5)	0.71855 (2)	0.04348 (12)
O1	0.34787 (17)	0.6979 (5)	1.1065 (4)	0.0461 (7)
H1	0.359 (2)	0.554 (4)	1.165 (7)	0.069*
N1	0.37448 (13)	0.7338 (5)	0.7440 (4)	0.0352 (7)
C1	0.60169 (15)	0.7091 (5)	0.7424 (4)	0.0304 (7)
C2	0.55354 (15)	0.5562 (6)	0.6774 (4)	0.0302 (7)
H2	0.5610	0.4194	0.6244	0.036*
C3	0.49499 (17)	0.6038 (5)	0.6903 (5)	0.0315 (7)
H3	0.4620	0.4989	0.6463	0.038*
C4	0.48338 (18)	0.8054 (6)	0.7676 (5)	0.0287 (8)
C5	0.53236 (16)	0.9557 (6)	0.8318 (4)	0.0315 (7)
H5	0.5249	1.0929	0.8844	0.038*
C6	0.59188 (17)	0.9099 (6)	0.8208 (5)	0.0347 (8)
H6	0.6252	1.0134	0.8658	0.042*
C7	0.42189 (16)	0.8625 (5)	0.7886 (5)	0.0310 (7)
H7	0.4173	1.0043	0.8386	0.037*
C8	0.31685 (17)	0.8097 (6)	0.7782 (6)	0.0387 (8)
H8A	0.2815	0.8034	0.6578	0.046*
H8B	0.3220	0.9656	0.8224	0.046*
C9	0.30217 (18)	0.6660 (6)	0.9269 (6)	0.0404 (8)
H9A	0.2600	0.7043	0.9354	0.048*
H9B	0.3016	0.5083	0.8893	0.048*

	U11	U22	U33	U12	U13	U23
Br1	0.03404 (18)	0.0539 (2)	0.04599 (18)	0.0060 (3)	0.01748 (12)	0.0006 (3)
O1	0.067 (2)	0.0296 (13)	0.0442 (18)	−0.0032 (15)	0.0204 (15)	−0.0002 (12)
N1	0.0358 (17)	0.0331 (16)	0.0399 (16)	0.0043 (13)	0.0164 (12)	0.0035 (13)
C1	0.0268 (18)	0.0386 (18)	0.0265 (16)	0.0057 (14)	0.0093 (13)	0.0052 (14)
C2	0.0363 (19)	0.0256 (16)	0.0297 (16)	0.0036 (14)	0.0114 (14)	0.0000 (14)
C3	0.040 (2)	0.0247 (16)	0.0302 (16)	−0.0039 (14)	0.0115 (14)	−0.0020 (13)
C4	0.038 (2)	0.0261 (16)	0.0236 (17)	0.0054 (16)	0.0112 (15)	0.0020 (13)
C5	0.039 (2)	0.0265 (18)	0.0300 (17)	0.0017 (15)	0.0117 (14)	−0.0028 (15)
C6	0.037 (2)	0.0335 (17)	0.0329 (17)	−0.0057 (15)	0.0094 (14)	−0.0030 (15)
C7	0.0360 (19)	0.0284 (17)	0.0301 (16)	0.0067 (14)	0.0125 (14)	0.0021 (13)
C8	0.0314 (19)	0.0397 (18)	0.047 (2)	0.0041 (15)	0.0153 (15)	0.0024 (16)
C9	0.036 (2)	0.0363 (18)	0.054 (2)	0.0014 (15)	0.0212 (17)	−0.0019 (17)

Br1—C1	1.900 (3)	C4—C5	1.387 (5)
O1—C9	1.413 (5)	C4—C7	1.471 (5)
O1—H1	0.968 (5)	C5—C6	1.385 (5)
N1—C7	1.272 (4)	C5—H5	0.9500
N1—C8	1.461 (4)	C6—H6	0.9500
C1—C2	1.386 (5)	C7—H7	0.9500
C1—C6	1.388 (5)	C8—C9	1.510 (5)
C2—C3	1.371 (5)	C8—H8A	0.9900
C2—H2	0.9500	C8—H8B	0.9900
C3—C4	1.401 (5)	C9—H9A	0.9900
C3—H3	0.9500	C9—H9B	0.9900
C9—O1—H1	108 (3)	C5—C6—H6	120.8
C7—N1—C8	118.2 (3)	C1—C6—H6	120.8
C2—C1—C6	121.3 (3)	N1—C7—C4	124.1 (3)
C2—C1—Br1	119.5 (3)	N1—C7—H7	117.9
C6—C1—Br1	119.2 (3)	C4—C7—H7	117.9
C3—C2—C1	119.5 (3)	N1—C8—C9	110.2 (3)
C3—C2—H2	120.2	N1—C8—H8A	109.6
C1—C2—H2	120.2	C9—C8—H8A	109.6
C2—C3—C4	120.7 (3)	N1—C8—H8B	109.6
C2—C3—H3	119.7	C9—C8—H8B	109.6
C4—C3—H3	119.7	H8A—C8—H8B	108.1
C5—C4—C3	118.7 (3)	O1—C9—C8	110.2 (3)
C5—C4—C7	118.4 (3)	O1—C9—H9A	109.6
C3—C4—C7	122.8 (3)	C8—C9—H9A	109.6
C6—C5—C4	121.4 (3)	O1—C9—H9B	109.6
C6—C5—H5	119.3	C8—C9—H9B	109.6
C4—C5—H5	119.3	H9A—C9—H9B	108.1
C5—C6—C1	118.5 (3)
C6—C1—C2—C3	0.1 (5)	C2—C1—C6—C5	−0.5 (5)
Br1—C1—C2—C3	−178.4 (2)	Br1—C1—C6—C5	178.1 (2)
C1—C2—C3—C4	0.2 (5)	C8—N1—C7—C4	178.1 (3)
C2—C3—C4—C5	−0.3 (5)	C5—C4—C7—N1	−176.3 (3)
C2—C3—C4—C7	−178.6 (3)	C3—C4—C7—N1	1.9 (5)
C3—C4—C5—C6	0.0 (5)	C7—N1—C8—C9	−115.0 (4)
C7—C4—C5—C6	178.3 (3)	N1—C8—C9—O1	67.6 (4)
C4—C5—C6—C1	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.97 (3)	1.83 (3)	2.791 (4)	172 (4)
C2—H2···Cg1ii	0.95	2.83	3.58 (3)	137
C5—H5···Cg1iii	0.95	2.79	3.512 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.97 (3)	1.83 (3)	2.791 (4)	172 (4)
C2—H2⋯Cg1ii	0.95	2.83	3.58 (3)	137
C5—H5⋯Cg1iii	0.95	2.79	3.512 (3)	134

Symmetry codes: (i) ; (ii) ; (iii) .