2,2,7,7-Tetra-methyl-1,2,3,4,5,6,7,8-octa-hydro-acridine-1,8-dione.

The whole molecule of the title compound, C17H21NO2, is generated by twofold rotational symmetry. The N atom and the C and H atoms in position 4 of the pyridine ring lie on the twofold axis. The cyclohexene ring has a sofa conformation with the CH2 C atom adjacent to the dimethyl-substituted C atom displaced by 0.5949 (16) Å from the mean plane of the other five C atoms. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into chains parallel to the a axis. In addition, π-π stacking inter-actions [centroid-centroid distance = 3.8444 (7) Å] contribute to the stabilization of the crystal structure.

Related literature

For background to potassium channels and biological functions and physiological roles, see: Horiuchi et al. (2001 ▶); Crestanello et al. (2000 ▶). For biological properties of 1,4-dihydro­n class="Chemical">pyridines (DHP), see: Simşek et al. (2004 ▶); Fincan et al. (2012 ▶); Gündüz et al. (2009 ▶); Pyrko (2008 ▶); Li et al. (2010 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For similar structures, see: El-Khouly et al. (2012 ▶); Öztürk Yildirim et al. (2012 ▶, 2013 ▶); Gündüz et al. (2012 ▶).

Experimental

Crystal data

C17H21NO2

M = 271.35

Tetragonal,

a = 9.99077 (19) Å

c = 14.5063 (4) Å

V = 1447.95 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.64 mm−1

T = 123 K

0.50 × 0.30 × 0.25 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.740, T max = 0.856

3055 measured reflections

1452 independent reflections

1349 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.122

S = 1.09

1452 reflections

94 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048957/mw2098sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048957/mw2098Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048957/mw2098Isup3.cml

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

C17H21NO2	Dx = 1.245 Mg m−3
Mr = 271.35	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P4322	Cell parameters from 1551 reflections
Hall symbol: P 4cw 2c	θ = 3.0–75.1°
a = 9.99077 (19) Å	µ = 0.64 mm−1
c = 14.5063 (4) Å	T = 123 K
V = 1447.95 (6) Å3	Block, colorless
Z = 4	0.50 × 0.30 × 0.25 mm
F(000) = 584

Agilent Xcalibur (Ruby, Gemini) diffractometer	1452 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1349 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 10.5081 pixels mm-1	θmax = 75.3°, θmin = 4.4°
ω scans	h = −11→12
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011), based on expressions derived by Clark & Reid (1995)]	k = −12→7
Tmin = 0.740, Tmax = 0.856	l = −12→18
3055 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0749P)2 + 0.0669P] where P = (Fo2 + 2Fc2)/3
1452 reflections	(Δ/σ)max < 0.001
94 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. Absorption correction: CrysAlis RED, (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. (Clark & Reid, 1995).

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	0.54930 (12)	0.19920 (12)	0.62530 (9)	0.0345 (3)
N1	0.66208 (13)	0.66208 (13)	0.6250	0.0259 (4)
C1	0.69529 (15)	0.53223 (15)	0.61859 (10)	0.0231 (3)
C2	0.84076 (15)	0.49870 (18)	0.60647 (12)	0.0288 (4)
H2A	0.8957	0.5649	0.6403	0.035*
H2B	0.8643	0.5049	0.5403	0.035*
C3	0.87361 (17)	0.35818 (18)	0.64155 (11)	0.0297 (4)
H3A	0.8671	0.3579	0.7096	0.036*
H3B	0.9674	0.3368	0.6251	0.036*
C4	0.78234 (16)	0.24795 (17)	0.60323 (11)	0.0254 (4)
C5	0.63570 (16)	0.28413 (16)	0.61821 (11)	0.0240 (3)
C6	0.59904 (15)	0.42923 (15)	0.62063 (10)	0.0218 (3)
C7	0.46519 (15)	0.46519 (15)	0.6250	0.0223 (4)
H7A	0.3980	0.3980	0.6250	0.027*
C8	0.79805 (17)	0.23165 (17)	0.49808 (12)	0.0319 (4)
H8A	0.7307	0.1685	0.4752	0.048*
H8B	0.8877	0.1974	0.4842	0.048*
H8C	0.7856	0.3186	0.4680	0.048*
C9	0.8130 (2)	0.1153 (2)	0.65133 (18)	0.0458 (6)
H9A	0.7559	0.0448	0.6257	0.069*
H9B	0.7955	0.1242	0.7175	0.069*
H9C	0.9072	0.0920	0.6416	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (6)	0.0225 (5)	0.0527 (8)	−0.0016 (5)	0.0096 (6)	0.0026 (6)
N1	0.0238 (6)	0.0238 (6)	0.0300 (9)	−0.0034 (7)	0.0020 (6)	−0.0020 (6)
C1	0.0220 (7)	0.0265 (8)	0.0209 (7)	−0.0006 (7)	0.0003 (6)	−0.0011 (6)
C2	0.0202 (7)	0.0309 (9)	0.0352 (8)	−0.0030 (6)	0.0014 (6)	−0.0046 (7)
C3	0.0222 (7)	0.0388 (9)	0.0283 (8)	0.0035 (7)	−0.0034 (7)	−0.0007 (7)
C4	0.0222 (8)	0.0251 (7)	0.0288 (8)	0.0040 (6)	0.0006 (6)	0.0038 (6)
C5	0.0233 (8)	0.0229 (8)	0.0257 (7)	0.0013 (6)	0.0033 (7)	0.0031 (6)
C6	0.0229 (7)	0.0227 (7)	0.0197 (7)	0.0001 (6)	0.0007 (6)	0.0020 (6)
C7	0.0213 (6)	0.0213 (6)	0.0243 (10)	−0.0026 (8)	−0.0004 (6)	0.0004 (6)
C8	0.0263 (8)	0.0357 (9)	0.0338 (9)	0.0008 (7)	0.0036 (7)	−0.0065 (8)
C9	0.0353 (10)	0.0389 (10)	0.0631 (13)	0.0080 (8)	−0.0002 (9)	0.0204 (10)

O1—C5	1.215 (2)	C4—C9	1.528 (2)
N1—C1	1.3423 (18)	C4—C8	1.542 (2)
N1—C1i	1.3423 (18)	C5—C6	1.496 (2)
C1—C6	1.409 (2)	C6—C7	1.3861 (17)
C1—C2	1.502 (2)	C7—C6i	1.3861 (17)
C2—C3	1.529 (2)	C7—H7A	0.9500
C2—H2A	0.9900	C8—H8A	0.9800
C2—H2B	0.9900	C8—H8B	0.9800
C3—C4	1.534 (2)	C8—H8C	0.9800
C3—H3A	0.9900	C9—H9A	0.9800
C3—H3B	0.9900	C9—H9B	0.9800
C4—C5	1.525 (2)	C9—H9C	0.9800
C1—N1—C1i	118.85 (19)	O1—C5—C6	120.07 (15)
N1—C1—C6	122.40 (14)	O1—C5—C4	121.96 (15)
N1—C1—C2	117.57 (14)	C6—C5—C4	117.93 (13)
C6—C1—C2	120.01 (14)	C7—C6—C1	118.05 (15)
C1—C2—C3	111.93 (14)	C7—C6—C5	119.24 (14)
C1—C2—H2A	109.2	C1—C6—C5	122.71 (14)
C3—C2—H2A	109.2	C6i—C7—C6	120.1 (2)
C1—C2—H2B	109.2	C6i—C7—H7A	119.9
C3—C2—H2B	109.2	C6—C7—H7A	119.9
H2A—C2—H2B	107.9	C4—C8—H8A	109.5
C2—C3—C4	114.27 (13)	C4—C8—H8B	109.5
C2—C3—H3A	108.7	H8A—C8—H8B	109.5
C4—C3—H3A	108.7	C4—C8—H8C	109.5
C2—C3—H3B	108.7	H8A—C8—H8C	109.5
C4—C3—H3B	108.7	H8B—C8—H8C	109.5
H3A—C3—H3B	107.6	C4—C9—H9A	109.5
C5—C4—C9	109.45 (15)	C4—C9—H9B	109.5
C5—C4—C3	110.45 (13)	H9A—C9—H9B	109.5
C9—C4—C3	109.74 (15)	C4—C9—H9C	109.5
C5—C4—C8	105.29 (13)	H9A—C9—H9C	109.5
C9—C4—C8	109.85 (16)	H9B—C9—H9C	109.5
C3—C4—C8	111.95 (14)
C1i—N1—C1—C6	−1.60 (11)	C3—C4—C5—C6	29.2 (2)
C1i—N1—C1—C2	176.83 (16)	C8—C4—C5—C6	−91.81 (16)
N1—C1—C2—C3	154.89 (12)	N1—C1—C6—C7	3.1 (2)
C6—C1—C2—C3	−26.6 (2)	C2—C1—C6—C7	−175.25 (13)
C1—C2—C3—C4	51.52 (19)	N1—C1—C6—C5	−176.91 (12)
C2—C3—C4—C5	−52.49 (18)	C2—C1—C6—C5	4.7 (2)
C2—C3—C4—C9	−173.25 (15)	O1—C5—C6—C7	−4.2 (2)
C2—C3—C4—C8	64.49 (18)	C4—C5—C6—C7	173.69 (12)
C9—C4—C5—O1	−32.0 (2)	O1—C5—C6—C1	175.89 (15)
C3—C4—C5—O1	−152.98 (16)	C4—C5—C6—C1	−6.3 (2)
C8—C4—C5—O1	85.99 (19)	C1—C6—C7—C6i	−1.48 (10)
C9—C4—C5—C6	150.15 (17)	C5—C6—C7—C6i	178.57 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1ii	0.99	2.52	3.415 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1i	0.99	2.52	3.415 (2)	151

Symmetry code: (i) .