rac-2-{[1-(1-Adamant­yl)eth­yl]imino­meth­yl}-5-meth­oxy­phenol

Jin, X.-D.; Wang, H.-B.; Jin, Y.-H.

doi:10.1107/S1600536811030522

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2233

doi:10.1107/S1600536811030522

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rac-2-{[1-(1-Adamantyl)ethyl]iminomethyl}-5-methoxyphenol

Xu-Dong Jin,^a ^* Hai-Bo Wang ^a and Yue-Hong Jin ^b

^aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China, and ^bLiaoning Provincial Institute of Measurement, Shenyang 110004, People's Republic of China
^*Correspondence e-mail: jinxudong@yahoo.com

(Received 1 July 2011; accepted 28 July 2011; online 2 August 2011)

A novel Schiff base compound, C₂₀H₂₇NO₂, was obtained by a condensation of rimantadine and 2-hydroxy-4-methoxybenzaldehyde. An intramolecular O—H⋯N hydrogen bond supports the phenol–imine tautomeric form. The adamantane and iminomethyl-4-methoxyphenol units are arranged in a folded conformation [C—N—C—C torsion angle = 110.9 (3)°]. In the crystal, highly hydrophobic adamantane moieties are inserted between the iminomethyl-4-methoxyphenol units in a sandwich-like arrangement along the c axis.

Related literature

For the synthesis of 2-((1-(1-adamantyl)ethyl)iminomethyl)-3-methoxyphenol, see: Shi et al. (2006 ). For related structures, see: Zhao et al. (2005 ). For amantadine derivatives, see: Jiang et al. (2011 ); Jin et al. (2011 ); Keyser et al. (2000 ).

Experimental

Crystal data

C₂₀H₂₇NO₂
M_r = 313.43
Monoclinic, P 2₁ /c
a = 9.9656 (12) Å
b = 16.1791 (17) Å
c = 11.6239 (13) Å
β = 113.575 (1)°
V = 1717.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.50 × 0.47 × 0.46 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.962, T_max = 0.965
8451 measured reflections
3016 independent reflections
1794 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.137
S = 1.06
3016 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.556 (3)	148

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811030522/kp2341sup1.cif

Supporting information file. DOI: 10.1107/S1600536811030522/kp2341Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030522/kp2341Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536811030522/kp2341Isup4.cml

checkCIF report

Comment top

There has been a considerable interest in compounds with adamantane attached to Schiff bases due to their biological activity. The title compound crystallises in the form of phenol-imine tautomer (Fig. 1) with O1—C3 bond length of 1.335 (3) Å. The N1=C10 bond length of 1.273 (3) Å is close to the value described by Shi et al. for N=C bond (1.263 (5) Å). Bond length of O2—C8 is 1.421 (3) Å. The torsion angle of C8—O2—C5—C4 is 6.6 (3)°. A strong O1—H···N1 intramolecular hydrogen bond stabilises the phenol-imine tautomer. A six-membered ring is formed by this hydrogen bond with O1···H1 distance of 0.820 Å and H1···N1 distance of 1.820 Å. The distance between N1 and O1 atom is 2.556 Å. The hydrogen bond angle O1—H1···N1 is 148.63°.

Related literature top

For the synthesis of 2-((1-(1-adamantyl)ethyl)iminomethyl)-3-methoxyphenol, see: Shi et al. (2006). For related structures, see: Zhao et al. (2005). For related literature [on what subjects?], see: Jiang et al. (2011); Jin et al. (2011); Keyser et al. (2000).

Experimental top

A mixture of rimantadine (0.54 g, 3.0 mmol) and 2-hydroxy-4-methoxybenzaldehyde (0.46 g, 3.0 mmol) in anhydrous alcohol (30 mL) was stirred and refluxed for ca 4 h. Then the solution was concentrated and left to stand at room temperature. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of a solvent in a few days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines indicate an intramolecular hydrogen bond.
	Fig. 2. A view of a packing of the title compound in sandwich -like fashion along the c axis.
	Fig. 3. The formation of the title compound.

rac-2-{[1-(1-Adamantyl)ethyl]iminomethyl}-5-methoxyphenol top

Crystal data top

C₂₀H₂₇NO₂	F(000) = 680
M_r = 313.43	D_x = 1.212 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 376.2 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.9656 (12) Å	Cell parameters from 2307 reflections
b = 16.1791 (17) Å	θ = 2.3–25.2°
c = 11.6239 (13) Å	µ = 0.08 mm⁻¹
β = 113.575 (1)°	T = 298 K
V = 1717.7 (3) Å³	Block, yellow
Z = 4	0.50 × 0.47 × 0.46 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3016 independent reflections
Radiation source: fine-focus sealed tube	1794 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→6
T_min = 0.962, T_max = 0.965	k = −18→19
8451 measured reflections	l = −13→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0447P)² + 0.732P] where P = (F_o² + 2F_c²)/3
3016 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₂₇NO₂	V = 1717.7 (3) Å³
M_r = 313.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9656 (12) Å	µ = 0.08 mm⁻¹
b = 16.1791 (17) Å	T = 298 K
c = 11.6239 (13) Å	0.50 × 0.47 × 0.46 mm
β = 113.575 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3016 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1794 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.965	R_int = 0.032
8451 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
3016 reflections	Δρ_min = −0.18 e Å⁻³
210 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
N1	0.7126 (2)	0.67451 (12)	0.40697 (18)	0.0536 (6)
O1	0.71762 (19)	0.61250 (12)	0.20647 (17)	0.0695 (6)
H1	0.7474	0.6253	0.2808	0.104*
O2	0.29257 (19)	0.64043 (11)	−0.17264 (15)	0.0613 (5)
C1	0.5815 (3)	0.69731 (14)	0.3429 (2)	0.0512 (6)
H1A	0.5313	0.7255	0.3832	0.061*
C2	0.5078 (3)	0.68105 (13)	0.2104 (2)	0.0430 (6)
C3	0.5797 (3)	0.63829 (14)	0.1467 (2)	0.0457 (6)
C4	0.5086 (3)	0.62210 (15)	0.0188 (2)	0.0482 (6)
H4	0.5559	0.5922	−0.0223	0.058*
C5	0.3691 (3)	0.65031 (14)	−0.0462 (2)	0.0459 (6)
C6	0.2963 (3)	0.69355 (16)	0.0147 (2)	0.0547 (7)
H6	0.2016	0.7129	−0.0298	0.066*
C7	0.3655 (3)	0.70733 (15)	0.1408 (2)	0.0530 (7)
H7	0.3155	0.7353	0.1815	0.064*
C8	0.3556 (3)	0.59070 (19)	−0.2388 (3)	0.0742 (9)
H8A	0.4444	0.6160	−0.2350	0.111*
H8B	0.2880	0.5858	−0.3249	0.111*
H8C	0.3769	0.5368	−0.2013	0.111*
C9	0.9245 (4)	0.7408 (2)	0.5605 (3)	0.0989 (12)
H9A	0.9899	0.7055	0.5409	0.148*
H9B	0.9710	0.7585	0.6464	0.148*
H9C	0.9008	0.7883	0.5064	0.148*
C10	0.7852 (3)	0.69376 (16)	0.5414 (2)	0.0572 (7)
H10	0.7210	0.7305	0.5634	0.069*
C11	0.8090 (2)	0.61413 (14)	0.6205 (2)	0.0415 (5)
C12	0.8917 (3)	0.54740 (15)	0.5831 (2)	0.0537 (7)
H12A	0.9874	0.5681	0.5939	0.064*
H12B	0.8386	0.5334	0.4953	0.064*
C13	0.9097 (3)	0.46995 (17)	0.6640 (2)	0.0644 (8)
H13	0.9618	0.4271	0.6386	0.077*
C14	0.9970 (3)	0.49280 (17)	0.8023 (2)	0.0635 (8)
H14A	1.0115	0.4441	0.8545	0.076*
H14B	1.0923	0.5142	0.8134	0.076*
C15	0.9132 (3)	0.55750 (16)	0.8406 (2)	0.0538 (7)
H15	0.9688	0.5721	0.9288	0.065*
C16	0.7645 (3)	0.52422 (19)	0.8248 (2)	0.0664 (8)
H16A	0.7765	0.4751	0.8758	0.080*
H16B	0.7124	0.5653	0.8519	0.080*
C17	0.6783 (3)	0.50353 (18)	0.6881 (2)	0.0656 (8)
H17	0.5814	0.4827	0.6767	0.079*
C18	0.6608 (3)	0.57904 (17)	0.6055 (2)	0.0585 (7)
H18A	0.6060	0.6211	0.6277	0.070*
H18B	0.6057	0.5640	0.5185	0.070*
C19	0.8941 (3)	0.63435 (15)	0.7596 (2)	0.0535 (7)
H19A	0.9896	0.6563	0.7722	0.064*
H19B	0.8420	0.6763	0.7850	0.064*
C20	0.7582 (4)	0.43828 (18)	0.6474 (3)	0.0766 (9)
H20A	0.7021	0.4243	0.5600	0.092*
H20B	0.7686	0.3887	0.6971	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0612 (15)	0.0518 (12)	0.0394 (12)	0.0056 (10)	0.0113 (11)	0.0069 (9)
O1	0.0574 (12)	0.0889 (14)	0.0548 (11)	0.0256 (10)	0.0148 (9)	0.0000 (10)
O2	0.0559 (11)	0.0824 (13)	0.0427 (11)	−0.0069 (9)	0.0169 (9)	−0.0063 (9)
C1	0.0656 (18)	0.0438 (14)	0.0444 (15)	0.0057 (12)	0.0223 (14)	0.0034 (11)
C2	0.0485 (15)	0.0403 (13)	0.0411 (13)	0.0035 (11)	0.0189 (12)	0.0038 (10)
C3	0.0444 (15)	0.0448 (14)	0.0464 (15)	0.0050 (11)	0.0166 (12)	0.0076 (11)
C4	0.0522 (16)	0.0524 (15)	0.0450 (14)	0.0041 (12)	0.0247 (13)	−0.0016 (11)
C5	0.0458 (15)	0.0518 (14)	0.0397 (14)	−0.0094 (11)	0.0168 (12)	−0.0006 (11)
C6	0.0412 (15)	0.0697 (17)	0.0499 (16)	0.0056 (12)	0.0147 (13)	0.0020 (13)
C7	0.0522 (16)	0.0591 (16)	0.0510 (16)	0.0080 (12)	0.0242 (13)	−0.0010 (12)
C8	0.089 (2)	0.082 (2)	0.0502 (17)	−0.0053 (17)	0.0263 (16)	−0.0154 (15)
C9	0.127 (3)	0.081 (2)	0.061 (2)	−0.045 (2)	0.008 (2)	0.0146 (17)
C10	0.0701 (19)	0.0519 (15)	0.0391 (14)	0.0037 (13)	0.0109 (13)	−0.0006 (12)
C11	0.0409 (13)	0.0481 (13)	0.0326 (12)	0.0007 (11)	0.0115 (10)	−0.0018 (10)
C12	0.0591 (16)	0.0621 (16)	0.0463 (14)	0.0076 (13)	0.0277 (13)	0.0031 (12)
C13	0.089 (2)	0.0580 (16)	0.0567 (17)	0.0246 (15)	0.0402 (16)	0.0096 (14)
C14	0.0623 (18)	0.0699 (18)	0.0592 (17)	0.0175 (14)	0.0252 (15)	0.0209 (14)
C15	0.0552 (16)	0.0680 (17)	0.0335 (13)	0.0038 (13)	0.0130 (12)	0.0029 (12)
C16	0.0627 (18)	0.091 (2)	0.0517 (16)	0.0056 (15)	0.0293 (14)	0.0127 (15)
C17	0.0522 (17)	0.087 (2)	0.0589 (18)	−0.0181 (15)	0.0230 (15)	0.0021 (15)
C18	0.0434 (15)	0.0805 (19)	0.0457 (15)	0.0005 (13)	0.0116 (12)	0.0027 (13)
C19	0.0570 (16)	0.0582 (16)	0.0390 (14)	0.0021 (13)	0.0128 (12)	−0.0044 (12)
C20	0.107 (3)	0.0621 (19)	0.0566 (18)	−0.0220 (17)	0.0288 (18)	0.0018 (14)

Geometric parameters (Å, º) top

N1—C1	1.273 (3)	C11—C18	1.526 (3)
N1—C10	1.469 (3)	C11—C19	1.531 (3)
O1—C3	1.335 (3)	C12—C13	1.534 (3)
O1—H1	0.8200	C12—H12A	0.9700
O2—C5	1.368 (3)	C12—H12B	0.9700
O2—C8	1.421 (3)	C13—C20	1.532 (4)
C1—C2	1.441 (3)	C13—C14	1.536 (4)
C1—H1A	0.9300	C13—H13	0.9800
C2—C7	1.389 (3)	C14—C15	1.512 (3)
C2—C3	1.402 (3)	C14—H14A	0.9700
C3—C4	1.392 (3)	C14—H14B	0.9700
C4—C5	1.368 (3)	C15—C16	1.518 (4)
C4—H4	0.9300	C15—C19	1.525 (3)
C5—C6	1.388 (3)	C15—H15	0.9800
C6—C7	1.366 (3)	C16—C17	1.511 (4)
C6—H6	0.9300	C16—H16A	0.9700
C7—H7	0.9300	C16—H16B	0.9700
C8—H8A	0.9600	C17—C20	1.508 (4)
C8—H8B	0.9600	C17—C18	1.520 (4)
C8—H8C	0.9600	C17—H17	0.9800
C9—C10	1.520 (4)	C18—H18A	0.9700
C9—H9A	0.9600	C18—H18B	0.9700
C9—H9B	0.9600	C19—H19A	0.9700
C9—H9C	0.9600	C19—H19B	0.9700
C10—C11	1.545 (3)	C20—H20A	0.9700
C10—H10	0.9800	C20—H20B	0.9700
C11—C12	1.523 (3)

C1—N1—C10	121.0 (2)	C11—C12—H12B	109.6
C3—O1—H1	109.5	C13—C12—H12B	109.6
C5—O2—C8	118.1 (2)	H12A—C12—H12B	108.1
N1—C1—C2	122.5 (2)	C20—C13—C12	109.2 (2)
N1—C1—H1A	118.7	C20—C13—C14	109.3 (2)
C2—C1—H1A	118.7	C12—C13—C14	108.9 (2)
C7—C2—C3	117.5 (2)	C20—C13—H13	109.8
C7—C2—C1	122.2 (2)	C12—C13—H13	109.8
C3—C2—C1	120.3 (2)	C14—C13—H13	109.8
O1—C3—C4	118.3 (2)	C15—C14—C13	109.0 (2)
O1—C3—C2	121.1 (2)	C15—C14—H14A	109.9
C4—C3—C2	120.5 (2)	C13—C14—H14A	109.9
C5—C4—C3	119.8 (2)	C15—C14—H14B	109.9
C5—C4—H4	120.1	C13—C14—H14B	109.9
C3—C4—H4	120.1	H14A—C14—H14B	108.3
C4—C5—O2	124.1 (2)	C14—C15—C16	110.3 (2)
C4—C5—C6	120.7 (2)	C14—C15—C19	109.3 (2)
O2—C5—C6	115.2 (2)	C16—C15—C19	109.9 (2)
C7—C6—C5	119.1 (2)	C14—C15—H15	109.1
C7—C6—H6	120.4	C16—C15—H15	109.1
C5—C6—H6	120.4	C19—C15—H15	109.1
C6—C7—C2	122.4 (2)	C17—C16—C15	108.8 (2)
C6—C7—H7	118.8	C17—C16—H16A	109.9
C2—C7—H7	118.8	C15—C16—H16A	109.9
O2—C8—H8A	109.5	C17—C16—H16B	109.9
O2—C8—H8B	109.5	C15—C16—H16B	109.9
H8A—C8—H8B	109.5	H16A—C16—H16B	108.3
O2—C8—H8C	109.5	C20—C17—C16	109.6 (2)
H8A—C8—H8C	109.5	C20—C17—C18	107.9 (2)
H8B—C8—H8C	109.5	C16—C17—C18	111.1 (2)
C10—C9—H9A	109.5	C20—C17—H17	109.4
C10—C9—H9B	109.5	C16—C17—H17	109.4
H9A—C9—H9B	109.5	C18—C17—H17	109.4
C10—C9—H9C	109.5	C17—C18—C11	111.4 (2)
H9A—C9—H9C	109.5	C17—C18—H18A	109.3
H9B—C9—H9C	109.5	C11—C18—H18A	109.3
N1—C10—C9	107.1 (2)	C17—C18—H18B	109.3
N1—C10—C11	110.45 (19)	C11—C18—H18B	109.3
C9—C10—C11	114.6 (2)	H18A—C18—H18B	108.0
N1—C10—H10	108.1	C15—C19—C11	110.9 (2)
C9—C10—H10	108.1	C15—C19—H19A	109.5
C11—C10—H10	108.1	C11—C19—H19A	109.5
C12—C11—C18	108.3 (2)	C15—C19—H19B	109.5
C12—C11—C19	108.55 (19)	C11—C19—H19B	109.5
C18—C11—C19	107.60 (19)	H19A—C19—H19B	108.0
C12—C11—C10	113.13 (19)	C17—C20—C13	110.1 (2)
C18—C11—C10	109.3 (2)	C17—C20—H20A	109.6
C19—C11—C10	109.80 (19)	C13—C20—H20A	109.6
C11—C12—C13	110.36 (19)	C17—C20—H20B	109.6
C11—C12—H12A	109.6	C13—C20—H20B	109.6
C13—C12—H12A	109.6	H20A—C20—H20B	108.2

C10—N1—C1—C2	178.7 (2)	C19—C11—C12—C13	58.6 (3)
N1—C1—C2—C7	−178.9 (2)	C10—C11—C12—C13	−179.3 (2)
N1—C1—C2—C3	0.3 (4)	C11—C12—C13—C20	58.7 (3)
C7—C2—C3—O1	178.6 (2)	C11—C12—C13—C14	−60.5 (3)
C1—C2—C3—O1	−0.7 (3)	C20—C13—C14—C15	−58.1 (3)
C7—C2—C3—C4	−1.0 (3)	C12—C13—C14—C15	61.0 (3)
C1—C2—C3—C4	179.7 (2)	C13—C14—C15—C16	60.1 (3)
O1—C3—C4—C5	−177.6 (2)	C13—C14—C15—C19	−60.8 (3)
C2—C3—C4—C5	2.0 (3)	C14—C15—C16—C17	−61.3 (3)
C3—C4—C5—O2	177.3 (2)	C19—C15—C16—C17	59.2 (3)
C3—C4—C5—C6	−1.4 (4)	C15—C16—C17—C20	60.8 (3)
C8—O2—C5—C4	6.6 (3)	C15—C16—C17—C18	−58.3 (3)
C8—O2—C5—C6	−174.7 (2)	C20—C17—C18—C11	−61.4 (3)
C4—C5—C6—C7	−0.3 (4)	C16—C17—C18—C11	58.8 (3)
O2—C5—C6—C7	−179.1 (2)	C12—C11—C18—C17	59.9 (3)
C5—C6—C7—C2	1.3 (4)	C19—C11—C18—C17	−57.2 (3)
C3—C2—C7—C6	−0.7 (4)	C10—C11—C18—C17	−176.4 (2)
C1—C2—C7—C6	178.6 (2)	C14—C15—C19—C11	60.2 (3)
C1—N1—C10—C9	−123.6 (3)	C16—C15—C19—C11	−60.9 (3)
C1—N1—C10—C11	110.9 (3)	C12—C11—C19—C15	−58.4 (3)
N1—C10—C11—C12	54.7 (3)	C18—C11—C19—C15	58.5 (3)
C9—C10—C11—C12	−66.5 (3)	C10—C11—C19—C15	177.4 (2)
N1—C10—C11—C18	−66.1 (3)	C16—C17—C20—C13	−60.2 (3)
C9—C10—C11—C18	172.8 (2)	C18—C17—C20—C13	60.8 (3)
N1—C10—C11—C19	176.1 (2)	C12—C13—C20—C17	−60.3 (3)
C9—C10—C11—C19	55.0 (3)	C14—C13—C20—C17	58.7 (3)
C18—C11—C12—C13	−57.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.556 (3)	148

Experimental details

Crystal data
Chemical formula	C₂₀H₂₇NO₂
M_r	313.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.9656 (12), 16.1791 (17), 11.6239 (13)
β (°)	113.575 (1)
V (Å³)	1717.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.47 × 0.46

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.962, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	8451, 3016, 1794
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.06
No. of reflections	3016
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.556 (3)	148

Acknowledgements

This work was supported financially by the Foundation of Liaoning Educational Committee (2008 T065), the Science and Technology Foundation of Liaoning Province (20071027) and the Scientific Research Foundation for Returned Overseas Chinese Scholars (2005546), China.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jiang, H., Jin, G., Cong, Z., Bao, L.-L., Qin, C. & Wei, Q. (2011). Chin. J. Comp. Med. 2, 23–25. Google Scholar
Jin, X.-D., Jin, Y.-H., Zou, Z.-Y., Cui, Z.-G., Wang, H.-B., Kang, P.-Li, Ge, C.-H. & Li, K. (2011). J. Coord. Chem. 64, 1533–1543. Web of Science CrossRef CAS Google Scholar
Keyser, L. A., Karl, M., Nafziger, A. N. & Bertino, J. S. (2000). Arch. Intern. Med. 160, 1485–1488. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, X., Lü, Z.-X. & Zhao, G.-L. (2006). Z. Kristallogr. New Cryst. Struct. 221, 145–147. CAS Google Scholar
Zhao, G.-L., Zhang, P.-H. & Feng, Y.-L. (2005). Chin. J. Inorg. Chem. 21, 421–424. CAS Google Scholar