(E)-2-{[2-(2-Hy-droxy-ethyl-amino)-ethyl-imino]-meth-yl}phenol.

The asymmetric unit of the title compound, C(11)H(16)N(2)O(2), contains two independent conformational isomers which show intra-molecular aromatic-imine O-H⋯N hydrogen bonds. In the crystal, neighboring mol-ecules are linked through inter-molecular aliphatic-aliphatic O-H⋯N, aliphatic-aromatic N-H⋯O and C-H⋯O inter-actions into hydrogen-bonded layers parallel to the ab plane.

Related literature

For crystal structures of metal complexes with this ligand, see: Haber et al. (2003 ▶); Kenar et al. (2001 ▶); Li et al. (1988 ▶); Rajendiran et al. (2007 ▶). For supra­molecular assemblies with structurally related ligands, see: Barba et al. (2000 ▶); Fujita et al. (2008 ▶); Höpfl (2002 ▶); Severin (2009 ▶). For the tautomerism of salicyl­idene­imines, see: Domínguez et al. (2011 ▶); Fujiwara et al. (2009 ▶); Ogawa et al. (1998 ▶); Rodríguez et al. (2007 ▶).

Experimental

Crystal data

C11H16N2O2

M = 208.26

Orthorhombic,

a = 7.0047 (11) Å

b = 14.171 (2) Å

c = 21.681 (3) Å

V = 2152.1 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.45 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.786, T max = 0.994

12054 measured reflections

2677 independent reflections

2311 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.115

S = 1.14

2677 reflections

289 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039997/pk2347sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039997/pk2347Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039997/pk2347Isup3.cml

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

C11H16N2O2	Dx = 1.286 Mg m−3
Mr = 208.26	Melting point: 358 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2547 reflections
a = 7.0047 (11) Å	θ = 2.9–25.4°
b = 14.171 (2) Å	µ = 0.09 mm−1
c = 21.681 (3) Å	T = 100 K
V = 2152.1 (6) Å3	Plate, yellow
Z = 8	0.45 × 0.08 × 0.07 mm
F(000) = 896

Bruker SMART CCD area-detector diffractometer	2677 independent reflections
Radiation source: fine-focus sealed tube	2311 reflections with I > 2σ(I)
graphite	Rint = 0.052
φ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.786, Tmax = 0.994	k = −9→18
12054 measured reflections	l = −27→24

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.4481P] where P = (Fo2 + 2Fc2)/3
2677 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.26 e Å−3
6 restraints	Δρmin = −0.24 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
O1	0.3350 (3)	0.69081 (15)	0.11061 (9)	0.0234 (5)
H1	0.442 (2)	0.674 (2)	0.1244 (14)	0.035*
O2	1.4419 (3)	0.62189 (16)	0.25568 (10)	0.0298 (5)
H2	1.453 (6)	0.5647 (7)	0.2462 (17)	0.045*
N1	0.6713 (3)	0.62184 (17)	0.12202 (11)	0.0210 (5)
N2	1.0729 (3)	0.69806 (18)	0.22607 (11)	0.0215 (6)
H2A	1.161 (3)	0.691 (2)	0.1990 (11)	0.032*
C1	0.3377 (4)	0.6585 (2)	0.05212 (13)	0.0193 (6)
C2	0.5001 (4)	0.61174 (19)	0.02788 (13)	0.0191 (6)
C3	0.4962 (4)	0.5809 (2)	−0.03349 (13)	0.0224 (6)
H3	0.6044	0.5495	−0.0502	0.027*
C4	0.3373 (5)	0.5954 (2)	−0.07020 (14)	0.0273 (7)
H4	0.3367	0.5744	−0.1118	0.033*
C5	0.1788 (5)	0.6408 (2)	−0.04570 (14)	0.0280 (7)
H5	0.0692	0.6505	−0.0707	0.034*
C6	0.1789 (4)	0.6719 (2)	0.01469 (14)	0.0231 (6)
H6	0.0693	0.7029	0.0308	0.028*
C7	0.6692 (4)	0.59821 (19)	0.06535 (13)	0.0194 (6)
H7	0.7802	0.5713	0.0474	0.023*
C8	0.8463 (4)	0.6083 (2)	0.15798 (13)	0.0232 (6)
H8A	0.9544	0.5946	0.1300	0.028*
H8B	0.8307	0.5540	0.1863	0.028*
C9	0.8875 (4)	0.6970 (2)	0.19473 (14)	0.0236 (7)
H9A	0.8811	0.7519	0.1665	0.028*
H9B	0.7858	0.7050	0.2260	0.028*
C10	1.0972 (4)	0.6245 (2)	0.27303 (13)	0.0251 (7)
H10A	1.0782	0.5616	0.2542	0.030*
H10B	1.0007	0.6327	0.3060	0.030*
C11	1.2954 (4)	0.6306 (2)	0.30039 (14)	0.0289 (7)
H11A	1.3094	0.6920	0.3218	0.035*
H11B	1.3106	0.5801	0.3315	0.035*
O31	−0.2420 (3)	0.35742 (16)	0.10565 (9)	0.0252 (5)
H31	−0.134 (2)	0.375 (2)	0.1175 (15)	0.038*
O32	0.8773 (3)	0.39234 (15)	0.25880 (11)	0.0279 (5)
H32	0.897 (5)	0.3345 (6)	0.2532 (17)	0.042*
N31	0.1079 (3)	0.41785 (17)	0.10613 (11)	0.0207 (5)
N32	0.4908 (3)	0.42869 (18)	0.22487 (11)	0.0196 (5)
H32A	0.586 (3)	0.423 (2)	0.2002 (12)	0.029*
C31	−0.2312 (4)	0.3602 (2)	0.04357 (13)	0.0204 (6)
C32	−0.0647 (4)	0.3916 (2)	0.01297 (13)	0.0198 (6)
C33	−0.0628 (4)	0.3926 (2)	−0.05144 (13)	0.0239 (7)
H33	0.0479	0.4145	−0.0723	0.029*
C34	−0.2171 (5)	0.3626 (2)	−0.08532 (14)	0.0272 (7)
H34	−0.2124	0.3630	−0.1291	0.033*
C35	−0.3797 (5)	0.3319 (2)	−0.05493 (15)	0.0284 (7)
H35	−0.4868	0.3110	−0.0781	0.034*
C36	−0.3872 (4)	0.3314 (2)	0.00889 (14)	0.0246 (7)
H36	−0.5003	0.3111	0.0291	0.029*
C37	0.1035 (4)	0.4199 (2)	0.04734 (13)	0.0203 (6)
H37	0.2133	0.4406	0.0255	0.024*
C38	0.2801 (4)	0.4497 (2)	0.13747 (13)	0.0219 (6)
H38A	0.2631	0.5160	0.1508	0.026*
H38B	0.3890	0.4476	0.1084	0.026*
C39	0.3245 (4)	0.3893 (2)	0.19290 (13)	0.0208 (6)
H39A	0.2133	0.3879	0.2211	0.025*
H39B	0.3519	0.3238	0.1796	0.025*
C40	0.5399 (4)	0.3768 (2)	0.28123 (13)	0.0228 (7)
H40A	0.5419	0.3082	0.2726	0.027*
H40B	0.4427	0.3889	0.3134	0.027*
C41	0.7342 (4)	0.4083 (2)	0.30387 (15)	0.0255 (7)
H41A	0.7297	0.4764	0.3140	0.031*
H41B	0.7669	0.3734	0.3420	0.031*

	U11	U22	U33	U12	U13	U23
O1	0.0208 (10)	0.0298 (12)	0.0194 (11)	0.0035 (9)	0.0004 (9)	−0.0023 (9)
O2	0.0253 (12)	0.0260 (12)	0.0380 (13)	0.0013 (10)	−0.0014 (10)	−0.0016 (11)
N1	0.0205 (12)	0.0191 (13)	0.0233 (13)	−0.0006 (11)	−0.0006 (10)	−0.0003 (11)
N2	0.0187 (12)	0.0240 (13)	0.0218 (13)	−0.0014 (11)	0.0016 (10)	0.0007 (11)
C1	0.0243 (14)	0.0148 (14)	0.0188 (14)	−0.0034 (12)	0.0020 (12)	0.0043 (11)
C2	0.0226 (13)	0.0136 (14)	0.0210 (14)	−0.0054 (12)	0.0016 (12)	0.0030 (12)
C3	0.0273 (15)	0.0174 (15)	0.0224 (15)	−0.0026 (12)	0.0068 (12)	−0.0001 (12)
C4	0.0421 (18)	0.0217 (16)	0.0180 (15)	−0.0037 (15)	−0.0049 (14)	0.0001 (12)
C5	0.0304 (16)	0.0258 (17)	0.0277 (17)	0.0000 (14)	−0.0102 (14)	0.0052 (14)
C6	0.0210 (14)	0.0193 (15)	0.0290 (16)	0.0014 (12)	−0.0009 (13)	0.0027 (13)
C7	0.0182 (13)	0.0151 (14)	0.0250 (15)	−0.0013 (11)	0.0050 (12)	−0.0007 (12)
C8	0.0221 (14)	0.0221 (16)	0.0254 (16)	0.0017 (13)	−0.0048 (12)	−0.0011 (13)
C9	0.0195 (14)	0.0241 (16)	0.0272 (16)	0.0015 (13)	−0.0013 (12)	−0.0028 (14)
C10	0.0264 (15)	0.0296 (18)	0.0193 (15)	−0.0036 (14)	0.0017 (12)	0.0002 (14)
C11	0.0311 (17)	0.0310 (18)	0.0248 (16)	0.0002 (14)	−0.0048 (13)	0.0001 (14)
O31	0.0219 (10)	0.0321 (13)	0.0217 (11)	−0.0051 (10)	0.0009 (9)	0.0000 (10)
O32	0.0225 (11)	0.0244 (12)	0.0369 (13)	0.0006 (10)	0.0018 (9)	0.0042 (11)
N31	0.0215 (12)	0.0195 (13)	0.0211 (13)	0.0013 (10)	0.0001 (10)	−0.0016 (10)
N32	0.0183 (12)	0.0219 (13)	0.0187 (13)	−0.0010 (10)	0.0023 (10)	0.0022 (11)
C31	0.0242 (14)	0.0150 (15)	0.0221 (15)	0.0026 (12)	−0.0019 (12)	−0.0020 (12)
C32	0.0226 (13)	0.0140 (14)	0.0227 (15)	0.0013 (12)	−0.0012 (12)	0.0005 (12)
C33	0.0274 (15)	0.0230 (17)	0.0213 (15)	0.0040 (13)	0.0038 (12)	0.0020 (13)
C34	0.0412 (18)	0.0218 (16)	0.0186 (15)	0.0020 (14)	−0.0053 (13)	−0.0011 (13)
C35	0.0336 (18)	0.0197 (16)	0.0319 (17)	0.0010 (14)	−0.0132 (14)	−0.0015 (14)
C36	0.0276 (15)	0.0163 (15)	0.0299 (17)	0.0009 (12)	0.0011 (13)	0.0018 (13)
C37	0.0199 (14)	0.0184 (15)	0.0225 (15)	0.0030 (12)	0.0032 (12)	0.0011 (12)
C38	0.0209 (14)	0.0220 (16)	0.0227 (15)	−0.0006 (12)	−0.0002 (11)	0.0016 (13)
C39	0.0170 (12)	0.0227 (16)	0.0228 (14)	−0.0021 (13)	−0.0007 (12)	−0.0004 (13)
C40	0.0239 (15)	0.0252 (17)	0.0192 (15)	0.0000 (13)	0.0013 (12)	0.0007 (13)
C41	0.0293 (15)	0.0241 (17)	0.0230 (15)	0.0030 (14)	−0.0055 (13)	−0.0003 (13)

O1—C1	1.349 (3)	O31—C31	1.349 (3)
O1—H1	0.8400 (11)	O31—H31	0.8401 (11)
O2—C11	1.417 (4)	O32—C41	1.418 (4)
O2—H2	0.8401 (11)	O32—H32	0.8400 (11)
N1—C7	1.274 (3)	N31—C37	1.275 (4)
N1—C8	1.466 (3)	N31—C38	1.456 (4)
N2—C9	1.466 (4)	N32—C39	1.466 (3)
N2—C10	1.467 (4)	N32—C40	1.467 (4)
N2—H2A	0.8600 (11)	N32—H32A	0.8600 (11)
C1—C6	1.391 (4)	C31—C36	1.388 (4)
C1—C2	1.417 (4)	C31—C32	1.413 (4)
C2—C3	1.401 (4)	C32—C33	1.397 (4)
C2—C7	1.448 (4)	C32—C37	1.451 (4)
C3—C4	1.383 (4)	C33—C34	1.374 (4)
C3—H3	0.9500	C33—H33	0.9500
C4—C5	1.389 (5)	C34—C35	1.386 (5)
C4—H4	0.9500	C34—H34	0.9500
C5—C6	1.382 (4)	C35—C36	1.385 (4)
C5—H5	0.9500	C35—H35	0.9500
C6—H6	0.9500	C36—H36	0.9500
C7—H7	0.9500	C37—H37	0.9500
C8—C9	1.516 (4)	C38—C39	1.508 (4)
C8—H8A	0.9900	C38—H38A	0.9900
C8—H8B	0.9900	C38—H38B	0.9900
C9—H9A	0.9900	C39—H39A	0.9900
C9—H9B	0.9900	C39—H39B	0.9900
C10—C11	1.512 (4)	C40—C41	1.514 (4)
C10—H10A	0.9900	C40—H40A	0.9900
C10—H10B	0.9900	C40—H40B	0.9900
C11—H11A	0.9900	C41—H41A	0.9900
C11—H11B	0.9900	C41—H41B	0.9900
C1—O1—H1	103 (2)	C31—O31—H31	104 (2)
C11—O2—H2	109 (3)	C41—O32—H32	112 (3)
C7—N1—C8	119.2 (3)	C37—N31—C38	118.6 (3)
C9—N2—C10	114.7 (2)	C39—N32—C40	112.9 (2)
C9—N2—H2A	109 (2)	C39—N32—H32A	107 (2)
C10—N2—H2A	108 (2)	C40—N32—H32A	107 (2)
O1—C1—C6	119.4 (3)	O31—C31—C36	119.2 (3)
O1—C1—C2	121.3 (3)	O31—C31—C32	121.6 (3)
C6—C1—C2	119.4 (3)	C36—C31—C32	119.2 (3)
C3—C2—C1	118.8 (3)	C33—C32—C31	118.7 (3)
C3—C2—C7	120.5 (3)	C33—C32—C37	120.2 (3)
C1—C2—C7	120.7 (2)	C31—C32—C37	121.1 (2)
C4—C3—C2	121.1 (3)	C34—C33—C32	121.6 (3)
C4—C3—H3	119.5	C34—C33—H33	119.2
C2—C3—H3	119.5	C32—C33—H33	119.2
C3—C4—C5	119.5 (3)	C33—C34—C35	119.3 (3)
C3—C4—H4	120.3	C33—C34—H34	120.4
C5—C4—H4	120.3	C35—C34—H34	120.4
C6—C5—C4	120.7 (3)	C36—C35—C34	120.5 (3)
C6—C5—H5	119.7	C36—C35—H35	119.7
C4—C5—H5	119.7	C34—C35—H35	119.7
C5—C6—C1	120.6 (3)	C35—C36—C31	120.6 (3)
C5—C6—H6	119.7	C35—C36—H36	119.7
C1—C6—H6	119.7	C31—C36—H36	119.7
N1—C7—C2	121.0 (3)	N31—C37—C32	121.8 (3)
N1—C7—H7	119.5	N31—C37—H37	119.1
C2—C7—H7	119.5	C32—C37—H37	119.1
N1—C8—C9	109.3 (2)	N31—C38—C39	111.5 (2)
N1—C8—H8A	109.8	N31—C38—H38A	109.3
C9—C8—H8A	109.8	C39—C38—H38A	109.3
N1—C8—H8B	109.8	N31—C38—H38B	109.3
C9—C8—H8B	109.8	C39—C38—H38B	109.3
H8A—C8—H8B	108.3	H38A—C38—H38B	108.0
N2—C9—C8	114.9 (2)	N32—C39—C38	108.9 (2)
N2—C9—H9A	108.5	N32—C39—H39A	109.9
C8—C9—H9A	108.5	C38—C39—H39A	109.9
N2—C9—H9B	108.5	N32—C39—H39B	109.9
C8—C9—H9B	108.5	C38—C39—H39B	109.9
H9A—C9—H9B	107.5	H39A—C39—H39B	108.3
N2—C10—C11	109.8 (3)	N32—C40—C41	109.5 (2)
N2—C10—H10A	109.7	N32—C40—H40A	109.8
C11—C10—H10A	109.7	C41—C40—H40A	109.8
N2—C10—H10B	109.7	N32—C40—H40B	109.8
C11—C10—H10B	109.7	C41—C40—H40B	109.8
H10A—C10—H10B	108.2	H40A—C40—H40B	108.2
O2—C11—C10	113.0 (2)	O32—C41—C40	111.4 (2)
O2—C11—H11A	109.0	O32—C41—H41A	109.3
C10—C11—H11A	109.0	C40—C41—H41A	109.3
O2—C11—H11B	109.0	O32—C41—H41B	109.3
C10—C11—H11B	109.0	C40—C41—H41B	109.3
H11A—C11—H11B	107.8	H41A—C41—H41B	108.0
O1—C1—C2—C3	−179.0 (3)	O31—C31—C32—C33	179.9 (3)
C6—C1—C2—C3	0.4 (4)	C36—C31—C32—C33	0.1 (4)
O1—C1—C2—C7	−0.6 (4)	O31—C31—C32—C37	1.5 (4)
C6—C1—C2—C7	178.8 (2)	C36—C31—C32—C37	−178.3 (3)
C1—C2—C3—C4	0.0 (4)	C31—C32—C33—C34	−1.0 (4)
C7—C2—C3—C4	−178.5 (3)	C37—C32—C33—C34	177.4 (3)
C2—C3—C4—C5	−0.4 (5)	C32—C33—C34—C35	0.9 (5)
C3—C4—C5—C6	0.4 (5)	C33—C34—C35—C36	0.1 (5)
C4—C5—C6—C1	0.0 (5)	C34—C35—C36—C31	−1.0 (5)
O1—C1—C6—C5	179.0 (3)	O31—C31—C36—C35	−178.9 (3)
C2—C1—C6—C5	−0.4 (4)	C32—C31—C36—C35	0.9 (4)
C8—N1—C7—C2	−179.0 (2)	C38—N31—C37—C32	−178.4 (2)
C3—C2—C7—N1	−176.6 (3)	C33—C32—C37—N31	−178.4 (3)
C1—C2—C7—N1	5.0 (4)	C31—C32—C37—N31	0.0 (4)
C7—N1—C8—C9	133.4 (3)	C37—N31—C38—C39	−141.5 (3)
C10—N2—C9—C8	−62.7 (3)	C40—N32—C39—C38	177.5 (2)
N1—C8—C9—N2	−171.8 (2)	N31—C38—C39—N32	−176.1 (2)
C9—N2—C10—C11	178.0 (2)	C39—N32—C40—C41	168.2 (2)
N2—C10—C11—O2	−57.8 (4)	N32—C40—C41—O32	−59.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84 (2)	1.77 (2)	2.562 (3)	157 (3)
O2—H2···N32i	0.84 (1)	2.00 (1)	2.839 (3)	178 (4)
N2—H2A···O1i	0.86 (2)	2.27 (2)	3.106 (3)	165 (2)
O31—H31···N31	0.84 (2)	1.82 (2)	2.596 (3)	154 (3)
O32—H32···N2ii	0.84 (1)	2.00 (1)	2.795 (3)	158 (4)
N32—H32A···O31i	0.86 (2)	2.55 (3)	3.347 (3)	154 (2)
C39—H39A···O32iii	0.99	2.49	3.443 (4)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84 (2)	1.77 (2)	2.562 (3)	157 (3)
O2—H2⋯N32i	0.84 (1)	2.00 (1)	2.839 (3)	178 (4)
N2—H2A⋯O1i	0.86 (2)	2.27 (2)	3.106 (3)	165 (2)
O31—H31⋯N31	0.84 (2)	1.82 (2)	2.596 (3)	154 (3)
O32—H32⋯N2ii	0.84 (1)	2.00 (1)	2.795 (3)	158 (4)
N32—H32A⋯O31i	0.86 (2)	2.55 (3)	3.347 (3)	154 (2)
C39—H39A⋯O32iii	0.99	2.49	3.443 (4)	161

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