(E)-2-{[2-(2-Hy­droxy­ethyl­amino)­ethyl­imino]­meth­yl}phenol

Germán-Acacio, J.M.; Tlahuext, H.; Höpfl, H.

doi:10.1107/S1600536811039997

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2849

doi:10.1107/S1600536811039997

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(E)-2-{[2-(2-Hydroxyethylamino)ethylimino]methyl}phenol

Juan M. Germán-Acacio,^a Hugo Tlahuext ^a and Herbert Höpfl ^a ^*

^aCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos. Av. Universidad 1001, CP 62209, Cuernavaca, Mexico
^*Correspondence e-mail: hhopfl@uaem.mx

(Received 14 September 2011; accepted 28 September 2011; online 5 October 2011)

The asymmetric unit of the title compound, C₁₁H₁₆N₂O₂, contains two independent conformational isomers which show intramolecular aromatic–imine O—H⋯N hydrogen bonds. In the crystal, neighboring molecules are linked through intermolecular aliphatic–aliphatic O—H⋯N, aliphatic–aromatic N—H⋯O and C—H⋯O interactions 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_r = 208.26
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.115
S = 1.14
2677 reflections
289 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) x+1, y, z; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811039997/pk2347sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811039997/pk2347Isup3.cml

checkCIF report

Comment top

The title compound (I) has been employed as a tri- and tetradentate ligand for the complexation of transition metal ions such as vanadium(IV), vanadium(V), copper(II) and cadmium(II) (Haber et al., 2003; Kenar et al., 2001; Li et al., 1988; Rajendiran et al., 2007). We are interested in this compound in the search for ligands capable of forming macrocyclic structures with boronic acids (Barba et al., 2000; Fujita et al., 2008; Höpfl, 2002; Severin, 2009).

The asymmetric unit of (I) contains two conformers (Ia, Ib) (Fig. 1) with similar bond lengths between equivalent non-H atoms (differences less than 3 s.u.). The torsion angles (C–C–N–C) in the fragments CH₂CH₂NHCH₂are +62.7 (3) and -177.5 (2)° for Ia and Ib, respectively, showing that Ia and Ib are conformational isomers. The dihedral angles in the NCH₂CH₂N ethylene fragments are -171.8 (2) and -176.1 (2)°, respectively.

From reports in the literature it is known that salicylidene imines form keto and enol tautomers, both in solution and the solid state (Domínguez et al., 2011; Fujiwara et al., 2009; Ogawa et al., 1998; Rodríguez et al., 2007). In the crystal structure both conformers correspond to the enol form. This is evidenced by the presence of an intramolecular O–H···N hydrogen bond formed between the phenolic OH group and the imine function, and a comparative analysis of the bond lengths within the salicylidene fragment. The values for the C_arom–O and C=N bond lengths with values of 1.349 (3) and 1.274 (3)–1.275 (4) Å, respectively, are within the range expected for enol tautomers. The same is true for the C_arom–C_arom bond lengths with values ranging from 1.374 (4)–1.417 (4) Å (Domínguez et al., 2011). From a careful crystallographic analysis of eight salicylidene aminoalcohols, Domínguez et al. concluded that the dominant hydrogen bonding pattern in the crystal structures of enol tautomers are intermolecular O–H···O interactions formed between the pendant NCH₂CH₂OH fragments of neighboring molecules. For keto tautomers, intermolecular O–H···O interactions typically involve the C_arom–O oxygen atom (Domínguez et al., 2011). In the crystal structure of the compound described herein, the crystallographically independent conformers are linked through O–H···N interactions between the pendant aliphatic NCH₂CH₂OH groups to give one-dimensional chains along axis b. Neighboring chains are further linked parallel to the a axis by N–H···O and C–H···O interactions involving as acceptor atoms the oxygen atoms of the phenolic and aliphatic O–H functions to form overall two-dimensional hydrogen bonded layers propagating parallel to the ab plane (Fig. 2).

Related literature top

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 top

For the preparation of (I), salicylaldehyde (0.234 g, 1.92 mmol) and 2-(2-aminoethylamino)ethanol (0.200 g, 1.92 mmol) were dissolved in 20 ml of ethanol. After reflux for 1 h, 60 ml of chloroform were added and the resulting solution was dried over anhydrous MgSO₄. Evaporation of the solvent mixture under vacuum gave a yellow oil. Crystals suitable for X-ray diffraction analysis were grown from a solution in chloroform, which was overlayered with n-hexane. Yield: 0.310 g (77%). M.p. 358 K.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Fragment of the 2D layer parallel to the ab plane, showing intramolecular O–H···N and intermolecular N–H···O, O–H···N and C–H···O hydrogen bonding interactions. These fragments are linked further through O2–H2···N32 hydrogen bonds to give the overall 2D layer. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

(E)-2-{[2-(2-Hydroxyethylamino)ethylimino]methyl}phenol top

Crystal data top

C₁₁H₁₆N₂O₂	D_x = 1.286 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0493P)² + 0.4481P] where P = (F_o² + 2F_c²)/3
2677 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.26 e Å⁻³
6 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₁H₁₆N₂O₂	V = 2152.1 (6) Å³
M_r = 208.26	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.0047 (11) Å	µ = 0.09 mm⁻¹
b = 14.171 (2) Å	T = 100 K
c = 21.681 (3) Å	0.45 × 0.08 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2677 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2311 reflections with I > 2σ(I)
T_min = 0.786, T_max = 0.994	R_int = 0.052
12054 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	6 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.26 e Å⁻³
2677 reflections	Δρ_min = −0.24 e Å⁻³
289 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+2, y−1/2, −z+1/2; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₆N₂O₂
M_r	208.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.0047 (11), 14.171 (2), 21.681 (3)
V (Å³)	2152.1 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.786, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	12054, 2677, 2311
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.115, 1.14
No. of reflections	2677
No. of parameters	289
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.24

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+2, y−1/2, −z+1/2; (iii) x−1, y, z.

Acknowledgements

This work was supported by the Consejo Nacional de Ciencia y Tecnología (CIAM-59213).

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