2-{[{2-Hy­droxy-3-[2-methyl-5-(propan-2-yl)phen­oxy]prop­yl}(pyridin-2-ylmeth­yl)amino]­meth­yl}phenol

Sancheti, R.S.; Dikundwar, A.G.; Bendre, R.S.

doi:10.1107/S1600536811020952

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1605

doi:10.1107/S1600536811020952

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2-{[{2-Hydroxy-3-[2-methyl-5-(propan-2-yl)phenoxy]propyl}(pyridin-2-ylmethyl)amino]methyl}phenol

Rakesh S. Sancheti,^a Amol G. Dikundwar ^b and Ratnamala S. Bendre ^a ^*

^aSchool of Chemical Sciences, North Maharashtra University, Jalgaon 425 001, India, and ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
^*Correspondence e-mail: bendrers@rediffmail.com

(Received 4 May 2011; accepted 31 May 2011; online 11 June 2011)

In the title racemic compound, C₂₆H₃₂N₂O₃, an intramolecular O—H⋯N hydrogen bond is formed between the phenolic OH group and the tertiary amine N atom. Another O—H⋯N hydrogen bond that is formed between the OH group and the pyridine N atom links the molecules into a polymeric chain extending along the a axis. The structure is further stabilized by intramolecular and intermolecular C—H⋯O interactions.

Related literature

For the synthesis of the title compound, see: Rossi et al. (2005 ). For related structures, see: Butcher et al. (2005 , 2007 ). For the activities of related metal complexes, see: Ruiz et al. (2010 ); Yajima et al. (2002 ); Sarkar et al. (2006 ); Neves et al. (1999 ).

Experimental

Crystal data

C₂₆H₃₂N₂O₃
M_r = 420.54
Triclinic, $[P \overline 1]$
a = 8.0940 (6) Å
b = 11.3611 (7) Å
c = 13.7625 (10) Å
α = 79.944 (6)°
β = 82.915 (6)°
γ = 71.745 (6)°
V = 1180.21 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.30 × 0.30 × 0.20 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.977, T_max = 0.985
23864 measured reflections
4083 independent reflections
3232 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.163
S = 1.06
4083 reflections
285 parameters
H-atom parameters constrained
Δρ_max = 0.99 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N2ⁱ	0.82	2.09	2.897 (2)	166
O3—H3⋯N1	0.82	1.99	2.721 (2)	147
C14—H14A⋯O2	0.97	2.51	3.199 (3)	128
C23—H23⋯O3ⁱⁱ	0.93	2.47	3.114 (3)	127
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020952/gk2373sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020952/gk2373Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020952/gk2373Isup3.cml

checkCIF report

Comment top

The chemistry of asymmetric polydentate ligands evokes interest, mainly towards the synthesis of biologically active coordination compounds. DNA metallointercalators have received considerable attention over the past few years because of their possible uses as new therapeutic agents and also for their interesting photochemical properties (Ruiz et al., 2010; Yajima et al., 2002; Sarkar et al., 2006). There are several reports on copper complexes of the asymmetrical ligands exhibiting important biological activities such as genomic and plasmid DNA cleavage and cytotoxic activity (Neves et al., 1999; Rossi et al., 2005).

The title compound was synthesized for preparation of metal complexes which would act as chemical nucleases. The ligand coordinates with a metal ion through its N₂O₂ donor set along with an additional halide ligand to form a complex with distorted trigonal bipyramidal geometry. The molecular conformation of the ligand is nonplanar with O—H···N and C—H···O intramolecular hydrogen bonds, both forming the six-membered rings (Fig. 1, Table 1). Packing of the molecules is mainly guided by the intermolecular O—H···N hydrogen bonds connecting the 1-(5-isopropyl-2-methylphenoxy)propan-2-ol fragment of one molecule to the pyridine fragment of the other.

Related literature top

For the synthesis of the title compound, see: Rossi et al. (2005). For related crystal structures, see: Butcher et al. (2005, 2007). For activities of related metal complexes, see: Ruiz et al. (2010); Yajima et al. (2002); Sarkar et al. (2006); Neves et al. (1999).

Experimental top

The title compound was synthesized by the reaction of 2-[(5-isopropyl-2-methylphenoxy)methyl]oxirane (5.8 mmol, 1.20 g) with N-(2-hydroxybenzyl)-N-(2-pyridylmethyl)amine (5.8 mmol, 1.23 g) in methanol under reflux condition at 70°C for 8 h. The reaction mixture was cooled, filtered and the precipitated product was washed with cold methanol in order to remove the impurities (yield 66%, m.p. 407K). Crystals suitable for X-ray diffraction were obtained by slow evaporation of the saturated solution in acetonitrile at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing intramolecular O—H···N hydrogen bond. Displacement ellipsoids are drawn at the 50% probability level. The H atom involved in intramolecular hydrogen bond is shown as a sphere of arbitrary radius.
	Fig. 2. Packing of the title compound viewed down the b axis. The dotted lines indicate intermolecular O—H···N interactions.

2-{[{2-Hydroxy-3-[2-methyl-5-(propan-2-yl)phenoxy]propyl}(pyridin-2- ylmethyl)amino]methyl}phenol top

Crystal data top

C₂₆H₃₂N₂O₃	Z = 2
M_r = 420.54	F(000) = 452
Triclinic, P1	D_x = 1.183 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0940 (6) Å	Cell parameters from 23864 reflections
b = 11.3611 (7) Å	θ = 2.6–25.0°
c = 13.7625 (10) Å	µ = 0.08 mm⁻¹
α = 79.944 (6)°	T = 120 K
β = 82.915 (6)°	Block, colourless
γ = 71.745 (6)°	0.30 × 0.30 × 0.20 mm
V = 1180.21 (15) Å³

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	4083 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3232 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→9
T_min = 0.977, T_max = 0.985	k = −13→13
23864 measured reflections	l = −16→16

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0984P)² + 0.1634P] where P = (F_o² + 2F_c²)/3
4083 reflections	(Δ/σ)_max < 0.001
285 parameters	Δρ_max = 0.99 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₆H₃₂N₂O₃	γ = 71.745 (6)°
M_r = 420.54	V = 1180.21 (15) Å³
Triclinic, P1	Z = 2
a = 8.0940 (6) Å	Mo Kα radiation
b = 11.3611 (7) Å	µ = 0.08 mm⁻¹
c = 13.7625 (10) Å	T = 120 K
α = 79.944 (6)°	0.30 × 0.30 × 0.20 mm
β = 82.915 (6)°

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	4083 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3232 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.985	R_int = 0.063
23864 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.06	Δρ_max = 0.99 e Å⁻³
4083 reflections	Δρ_min = −0.27 e Å⁻³
285 parameters

Special details top

Experimental. 1H NMR (p.p.m., CDCl₃): 1.20 (d, 6H, 2-CH₃), 2.08 (s, 3H, –CH₃), 2.84 (d, 2H, –CH₂), 3.10 (m, 1H, –CH), 3.90 (m, 4H 2-CH₂), 4.10(d, 2H, –CH₂), 4.25 (m, 1H, –CH), 4.58 (bs, 1H, Ar—OH), 6.7 to 7.7 Ar—H. (Found: C 74.54, H 7.37, N 6.67%; Calcd. for C₂₆H₃₁O₃N₂: C 74.44, H 7.44, N 7.05%) IR (cm-l): ? (C═C) 1586, ? (C—O—C) 1151. MS (m/z): 421[M]+

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.7021 (3)	0.58331 (18)	0.23411 (15)	0.0272 (5)
H1	0.6049	0.5897	0.2789	0.033*
C2	0.6851 (3)	0.65628 (19)	0.14101 (15)	0.0289 (5)
C3	0.8326 (3)	0.6470 (2)	0.07647 (15)	0.0308 (5)
H3A	0.8240	0.6956	0.0144	0.037*
C4	0.9931 (3)	0.5658 (2)	0.10358 (16)	0.0317 (5)
H4	1.0904	0.5613	0.0591	0.038*
C5	1.0125 (3)	0.49111 (18)	0.19502 (16)	0.0287 (5)
C6	0.8624 (3)	0.50136 (18)	0.26044 (15)	0.0260 (5)
C7	0.5086 (3)	0.7432 (2)	0.11150 (16)	0.0323 (5)
H7	0.5243	0.7825	0.0431	0.039*
C8	0.4387 (3)	0.8471 (2)	0.17527 (18)	0.0375 (5)
H8A	0.4249	0.8112	0.2432	0.056*
H8B	0.3278	0.9006	0.1540	0.056*
H8C	0.5191	0.8952	0.1689	0.056*
C9	0.3783 (3)	0.6693 (2)	0.11357 (17)	0.0360 (5)
H9A	0.4214	0.6093	0.0683	0.054*
H9B	0.2678	0.7260	0.0945	0.054*
H9C	0.3643	0.6266	0.1792	0.054*
C10	1.1857 (3)	0.4025 (2)	0.22438 (18)	0.0381 (5)
H10A	1.2731	0.4077	0.1712	0.057*
H10B	1.1780	0.3185	0.2383	0.057*
H10C	1.2168	0.4246	0.2823	0.057*
C11	0.7519 (3)	0.43452 (19)	0.42513 (16)	0.0290 (5)
H11A	0.6481	0.4302	0.3992	0.035*
H11B	0.7242	0.5131	0.4511	0.035*
C12	0.8149 (3)	0.32503 (19)	0.50560 (16)	0.0300 (5)
H12	0.8512	0.2478	0.4757	0.036*
C13	0.9716 (3)	0.33436 (18)	0.55172 (15)	0.0249 (4)
H13A	1.0516	0.3589	0.4995	0.030*
H13B	0.9321	0.3992	0.5940	0.030*
C14	0.9973 (3)	0.20672 (18)	0.71470 (14)	0.0253 (4)
H14A	0.8710	0.2386	0.7183	0.030*
H14B	1.0401	0.2583	0.7484	0.030*
C15	1.0514 (2)	0.07363 (18)	0.76661 (14)	0.0247 (4)
C16	1.0327 (3)	−0.02368 (19)	0.72237 (15)	0.0271 (5)
C17	1.0661 (3)	−0.1443 (2)	0.77277 (17)	0.0345 (5)
H17	1.0498	−0.2074	0.7436	0.041*
C18	1.1244 (3)	−0.1707 (2)	0.86749 (17)	0.0392 (6)
H18	1.1463	−0.2515	0.9018	0.047*
C19	1.1499 (3)	−0.0776 (2)	0.91064 (17)	0.0404 (6)
H19	1.1928	−0.0960	0.9729	0.048*
C20	1.1114 (3)	0.0433 (2)	0.86082 (15)	0.0326 (5)
H20	1.1260	0.1061	0.8912	0.039*
C21	1.2544 (2)	0.19811 (18)	0.60307 (14)	0.0239 (4)
H21A	1.3081	0.1279	0.6517	0.029*
H21B	1.2744	0.2722	0.6189	0.029*
C22	1.3400 (2)	0.17410 (17)	0.50250 (14)	0.0227 (4)
C23	1.2875 (3)	0.10394 (18)	0.44568 (15)	0.0273 (5)
H23	1.1955	0.0716	0.4694	0.033*
C24	1.3720 (3)	0.08254 (19)	0.35424 (15)	0.0290 (5)
H24	1.3369	0.0368	0.3153	0.035*
C25	1.5104 (3)	0.13057 (19)	0.32132 (16)	0.0298 (5)
H25	1.5707	0.1177	0.2602	0.036*
C26	1.5555 (3)	0.19783 (19)	0.38222 (15)	0.0296 (5)
H26	1.6486	0.2295	0.3603	0.036*
N1	1.0650 (2)	0.21620 (14)	0.61015 (12)	0.0226 (4)
N2	1.4744 (2)	0.22078 (16)	0.47087 (13)	0.0275 (4)
O1	0.89021 (18)	0.42567 (13)	0.34963 (11)	0.0313 (4)
O2	0.67674 (19)	0.31938 (15)	0.57718 (11)	0.0354 (4)
H2O	0.6056	0.2961	0.5541	0.053*
O3	0.9810 (2)	−0.00092 (14)	0.62858 (11)	0.0341 (4)
H3	0.9930	0.0662	0.6008	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0266 (11)	0.0251 (10)	0.0336 (11)	−0.0092 (9)	−0.0063 (9)	−0.0082 (9)
C2	0.0310 (11)	0.0274 (11)	0.0339 (11)	−0.0117 (9)	−0.0080 (9)	−0.0095 (9)
C3	0.0360 (12)	0.0321 (11)	0.0292 (11)	−0.0144 (10)	−0.0062 (9)	−0.0069 (9)
C4	0.0331 (12)	0.0330 (12)	0.0339 (12)	−0.0137 (9)	−0.0015 (9)	−0.0118 (9)
C5	0.0284 (11)	0.0240 (11)	0.0388 (12)	−0.0095 (9)	−0.0058 (9)	−0.0130 (9)
C6	0.0299 (11)	0.0211 (10)	0.0311 (11)	−0.0110 (8)	−0.0077 (9)	−0.0046 (8)
C7	0.0294 (12)	0.0343 (12)	0.0348 (12)	−0.0112 (9)	−0.0108 (9)	0.0002 (9)
C8	0.0324 (12)	0.0311 (12)	0.0490 (14)	−0.0083 (10)	−0.0068 (10)	−0.0054 (10)
C9	0.0305 (12)	0.0404 (13)	0.0405 (13)	−0.0115 (10)	−0.0118 (10)	−0.0067 (10)
C10	0.0310 (12)	0.0325 (12)	0.0520 (14)	−0.0095 (10)	−0.0037 (10)	−0.0089 (10)
C11	0.0221 (10)	0.0265 (11)	0.0411 (12)	−0.0101 (8)	−0.0090 (9)	−0.0017 (9)
C12	0.0243 (11)	0.0282 (11)	0.0400 (12)	−0.0124 (9)	−0.0072 (9)	0.0004 (9)
C13	0.0250 (10)	0.0218 (10)	0.0299 (11)	−0.0093 (8)	−0.0039 (8)	−0.0037 (8)
C14	0.0224 (10)	0.0273 (11)	0.0295 (11)	−0.0098 (8)	−0.0028 (8)	−0.0080 (8)
C15	0.0205 (10)	0.0268 (11)	0.0284 (11)	−0.0096 (8)	0.0007 (8)	−0.0051 (8)
C16	0.0210 (10)	0.0309 (11)	0.0324 (11)	−0.0130 (8)	0.0009 (8)	−0.0049 (9)
C17	0.0313 (12)	0.0284 (12)	0.0455 (14)	−0.0137 (9)	0.0033 (10)	−0.0056 (10)
C18	0.0390 (13)	0.0298 (12)	0.0408 (13)	−0.0083 (10)	0.0062 (10)	0.0056 (10)
C19	0.0426 (14)	0.0411 (14)	0.0304 (12)	−0.0066 (11)	−0.0015 (10)	0.0017 (10)
C20	0.0313 (12)	0.0357 (12)	0.0307 (11)	−0.0089 (9)	−0.0001 (9)	−0.0079 (9)
C21	0.0192 (10)	0.0240 (10)	0.0324 (11)	−0.0092 (8)	−0.0057 (8)	−0.0064 (8)
C22	0.0180 (9)	0.0196 (10)	0.0316 (11)	−0.0063 (8)	−0.0064 (8)	−0.0018 (8)
C23	0.0221 (10)	0.0275 (11)	0.0375 (12)	−0.0123 (8)	−0.0034 (9)	−0.0083 (9)
C24	0.0245 (10)	0.0284 (11)	0.0370 (12)	−0.0064 (9)	−0.0058 (9)	−0.0131 (9)
C25	0.0230 (10)	0.0302 (11)	0.0348 (12)	−0.0049 (9)	−0.0009 (9)	−0.0076 (9)
C26	0.0233 (10)	0.0336 (12)	0.0362 (12)	−0.0141 (9)	0.0013 (9)	−0.0080 (9)
N1	0.0183 (8)	0.0230 (8)	0.0288 (9)	−0.0082 (7)	−0.0039 (7)	−0.0042 (7)
N2	0.0230 (9)	0.0280 (9)	0.0362 (10)	−0.0127 (7)	−0.0032 (7)	−0.0073 (7)
O1	0.0266 (8)	0.0294 (8)	0.0365 (8)	−0.0063 (6)	−0.0073 (6)	−0.0015 (6)
O2	0.0309 (9)	0.0410 (9)	0.0389 (9)	−0.0168 (7)	−0.0047 (7)	−0.0051 (7)
O3	0.0400 (9)	0.0315 (8)	0.0405 (9)	−0.0206 (7)	−0.0123 (7)	−0.0054 (7)

Geometric parameters (Å, º) top

C1—C6	1.386 (3)	C13—H13B	0.9700
C1—C2	1.396 (3)	C14—N1	1.473 (3)
C1—H1	0.9300	C14—C15	1.508 (3)
C2—C3	1.384 (3)	C14—H14A	0.9700
C2—C7	1.516 (3)	C14—H14B	0.9700
C3—C4	1.388 (3)	C15—C20	1.389 (3)
C3—H3A	0.9300	C15—C16	1.407 (3)
C4—C5	1.386 (3)	C16—O3	1.362 (2)
C4—H4	0.9300	C16—C17	1.384 (3)
C5—C6	1.406 (3)	C17—C18	1.392 (3)
C5—C10	1.502 (3)	C17—H17	0.9300
C6—O1	1.369 (2)	C18—C19	1.378 (3)
C7—C8	1.518 (3)	C18—H18	0.9300
C7—C9	1.535 (3)	C19—C20	1.382 (3)
C7—H7	0.9800	C19—H19	0.9300
C8—H8A	0.9600	C20—H20	0.9300
C8—H8B	0.9600	C21—N1	1.474 (2)
C8—H8C	0.9600	C21—C22	1.499 (3)
C9—H9A	0.9600	C21—H21A	0.9700
C9—H9B	0.9600	C21—H21B	0.9700
C9—H9C	0.9600	C22—N2	1.348 (3)
C10—H10A	0.9600	C22—C23	1.393 (3)
C10—H10B	0.9600	C23—C24	1.379 (3)
C10—H10C	0.9600	C23—H23	0.9300
C11—O1	1.422 (3)	C24—C25	1.389 (3)
C11—C12	1.515 (3)	C24—H24	0.9300
C11—H11A	0.9700	C25—C26	1.376 (3)
C11—H11B	0.9700	C25—H25	0.9300
C12—O2	1.406 (3)	C26—N2	1.339 (3)
C12—C13	1.526 (3)	C26—H26	0.9300
C12—H12	0.9800	O2—H2O	0.8200
C13—N1	1.469 (2)	O3—H3	0.8200
C13—H13A	0.9700

C6—C1—C2	120.7 (2)	C12—C13—H13A	109.0
C6—C1—H1	119.7	N1—C13—H13B	109.0
C2—C1—H1	119.7	C12—C13—H13B	109.0
C3—C2—C1	118.5 (2)	H13A—C13—H13B	107.8
C3—C2—C7	120.99 (19)	N1—C14—C15	111.99 (16)
C1—C2—C7	120.52 (19)	N1—C14—H14A	109.2
C2—C3—C4	120.6 (2)	C15—C14—H14A	109.2
C2—C3—H3A	119.7	N1—C14—H14B	109.2
C4—C3—H3A	119.7	C15—C14—H14B	109.2
C5—C4—C3	121.9 (2)	H14A—C14—H14B	107.9
C5—C4—H4	119.1	C20—C15—C16	117.71 (18)
C3—C4—H4	119.1	C20—C15—C14	121.98 (18)
C4—C5—C6	117.28 (19)	C16—C15—C14	120.21 (17)
C4—C5—C10	122.1 (2)	O3—C16—C17	118.51 (19)
C6—C5—C10	120.66 (19)	O3—C16—C15	120.51 (18)
O1—C6—C1	124.48 (19)	C17—C16—C15	120.97 (19)
O1—C6—C5	114.48 (18)	C16—C17—C18	119.5 (2)
C1—C6—C5	121.04 (19)	C16—C17—H17	120.2
C2—C7—C8	111.83 (17)	C18—C17—H17	120.2
C2—C7—C9	110.83 (17)	C19—C18—C17	120.3 (2)
C8—C7—C9	111.36 (19)	C19—C18—H18	119.8
C2—C7—H7	107.5	C17—C18—H18	119.8
C8—C7—H7	107.5	C18—C19—C20	119.7 (2)
C9—C7—H7	107.5	C18—C19—H19	120.2
C7—C8—H8A	109.5	C20—C19—H19	120.2
C7—C8—H8B	109.5	C19—C20—C15	121.7 (2)
H8A—C8—H8B	109.5	C19—C20—H20	119.1
C7—C8—H8C	109.5	C15—C20—H20	119.1
H8A—C8—H8C	109.5	N1—C21—C22	112.97 (15)
H8B—C8—H8C	109.5	N1—C21—H21A	109.0
C7—C9—H9A	109.5	C22—C21—H21A	109.0
C7—C9—H9B	109.5	N1—C21—H21B	109.0
H9A—C9—H9B	109.5	C22—C21—H21B	109.0
C7—C9—H9C	109.5	H21A—C21—H21B	107.8
H9A—C9—H9C	109.5	N2—C22—C23	121.50 (19)
H9B—C9—H9C	109.5	N2—C22—C21	116.56 (16)
C5—C10—H10A	109.5	C23—C22—C21	121.91 (17)
C5—C10—H10B	109.5	C24—C23—C22	119.90 (19)
H10A—C10—H10B	109.5	C24—C23—H23	120.1
C5—C10—H10C	109.5	C22—C23—H23	120.1
H10A—C10—H10C	109.5	C23—C24—C25	118.79 (19)
H10B—C10—H10C	109.5	C23—C24—H24	120.6
O1—C11—C12	106.52 (16)	C25—C24—H24	120.6
O1—C11—H11A	110.4	C26—C25—C24	117.8 (2)
C12—C11—H11A	110.4	C26—C25—H25	121.1
O1—C11—H11B	110.4	C24—C25—H25	121.1
C12—C11—H11B	110.4	N2—C26—C25	124.49 (19)
H11A—C11—H11B	108.6	N2—C26—H26	117.8
O2—C12—C11	109.42 (16)	C25—C26—H26	117.8
O2—C12—C13	111.46 (17)	C13—N1—C14	112.26 (15)
C11—C12—C13	111.23 (16)	C13—N1—C21	111.67 (15)
O2—C12—H12	108.2	C14—N1—C21	110.08 (15)
C11—C12—H12	108.2	C26—N2—C22	117.52 (17)
C13—C12—H12	108.2	C6—O1—C11	119.89 (15)
N1—C13—C12	112.82 (15)	C12—O2—H2O	109.5
N1—C13—H13A	109.0	C16—O3—H3	109.5

C6—C1—C2—C3	−1.4 (3)	O3—C16—C17—C18	177.95 (19)
C6—C1—C2—C7	178.34 (17)	C15—C16—C17—C18	−2.0 (3)
C1—C2—C3—C4	0.7 (3)	C16—C17—C18—C19	−0.5 (3)
C7—C2—C3—C4	−179.02 (18)	C17—C18—C19—C20	2.3 (3)
C2—C3—C4—C5	0.2 (3)	C18—C19—C20—C15	−1.7 (3)
C3—C4—C5—C6	−0.5 (3)	C16—C15—C20—C19	−0.7 (3)
C3—C4—C5—C10	179.60 (18)	C14—C15—C20—C19	175.7 (2)
C2—C1—C6—O1	−179.35 (17)	N1—C21—C22—N2	145.52 (17)
C2—C1—C6—C5	1.2 (3)	N1—C21—C22—C23	−36.4 (2)
C4—C5—C6—O1	−179.73 (17)	N2—C22—C23—C24	−1.0 (3)
C10—C5—C6—O1	0.2 (3)	C21—C22—C23—C24	−178.94 (18)
C4—C5—C6—C1	−0.2 (3)	C22—C23—C24—C25	0.9 (3)
C10—C5—C6—C1	179.71 (18)	C23—C24—C25—C26	−0.2 (3)
C3—C2—C7—C8	−115.7 (2)	C24—C25—C26—N2	−0.4 (3)
C1—C2—C7—C8	64.5 (3)	C12—C13—N1—C14	−90.37 (19)
C3—C2—C7—C9	119.4 (2)	C12—C13—N1—C21	145.45 (17)
C1—C2—C7—C9	−60.4 (3)	C15—C14—N1—C13	162.17 (15)
O1—C11—C12—O2	−172.92 (15)	C15—C14—N1—C21	−72.78 (19)
O1—C11—C12—C13	63.5 (2)	C22—C21—N1—C13	−69.2 (2)
O2—C12—C13—N1	72.9 (2)	C22—C21—N1—C14	165.45 (15)
C11—C12—C13—N1	−164.73 (17)	C25—C26—N2—C22	0.3 (3)
N1—C14—C15—C20	136.15 (19)	C23—C22—N2—C26	0.4 (3)
N1—C14—C15—C16	−47.5 (2)	C21—C22—N2—C26	178.44 (17)
C20—C15—C16—O3	−177.38 (18)	C1—C6—O1—C11	−4.5 (3)
C14—C15—C16—O3	6.1 (3)	C5—C6—O1—C11	175.02 (16)
C20—C15—C16—C17	2.6 (3)	C12—C11—O1—C6	170.36 (15)
C14—C15—C16—C17	−173.90 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N2ⁱ	0.82	2.09	2.897 (2)	166
O3—H3···N1	0.82	1.99	2.721 (2)	147
C14—H14A···O2	0.97	2.51	3.199 (3)	128
C23—H23···O3ⁱⁱ	0.93	2.47	3.114 (3)	127

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₂N₂O₃
M_r	420.54
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.0940 (6), 11.3611 (7), 13.7625 (10)
α, β, γ (°)	79.944 (6), 82.915 (6), 71.745 (6)
V (Å³)	1180.21 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.977, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	23864, 4083, 3232
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.163, 1.06
No. of reflections	4083
No. of parameters	285
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.99, −0.27

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N2ⁱ	0.82	2.09	2.897 (2)	166
O3—H3···N1	0.82	1.99	2.721 (2)	147
C14—H14A···O2	0.97	2.51	3.199 (3)	128
C23—H23···O3ⁱⁱ	0.93	2.47	3.114 (3)	127

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+1.

Acknowledgements

The authors thank the DST, India, for funding under DST-FIST (Level II) for the X-ray diffraction facility at SSCU, Indian Institute of Science, Bangalore.

References

Butcher, R. J., Bendre, R. S. & Kuwar, A. S. (2005). Acta Cryst. E61, o3511–o3513. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 67| Part 7| July 2011| Page o1605

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-{[{2-Hy­dr­oxy-3-[2-methyl-5-(propan-2-yl)phen­­oxy]prop­yl}(pyridin-2-ylmeth­yl)amino]­meth­yl}phenol

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Experimental

Crystal data

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organic compounds

2-{[{2-Hydroxy-3-[2-methyl-5-(propan-2-yl)phenoxy]propyl}(pyridin-2-ylmethyl)amino]methyl}phenol