rac-2-{[1-(1-Adamant-yl)eth-yl]imino-meth-yl}-5-meth-oxy-phenol.

A novel Schiff base compound, C(20)H(27)NO(2), was obtained by a condensation of rimantadine and 2-hy-droxy-4-meth-oxy-benzaldehyde. An intra-molecular O-H⋯N hydrogen bond supports the phenol-imine tautomeric form. The adamantane and imino-methyl-4-meth-oxy-phenol units are arranged in a folded conformation [C-N-C-C torsion angle = 110.9 (3)°]. In the crystal, highly hydro-phobic adamantane moieties are inserted between the imino-methyl-4-meth-oxy-phenol 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 = 313.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.137

S = 1.06

3016 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811030522/kp2341sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811030522/kp2341Isup2.cdx

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

Supplementary material file. DOI: 10.1107/S1600536811030522/kp2341Isup4.cml

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

C20H27NO2	F(000) = 680
Mr = 313.43	Dx = 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

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

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(Fo2) + (0.0447P)2 + 0.732P] where P = (Fo2 + 2Fc2)/3
3016 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.18 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
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*

	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)

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)

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

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