2-Meth-oxy-4-(2-meth-oxy-phen-yl)-5,6,7,8,9,10-hexa-hydro-cyclo-octa-[b]pyridine-3-carbo-nitrile.

In the title compound, C20H22N2O2, the central pyridine ring forms a dihedral angle of 76.32 (8)° with the pseudo-axial benzene ring. The cyclo-octane ring adopts a twisted boat chair conformation. In the crystal, weak inter-molecular C-H⋯π inter-actions between inversion-related mol-ecules result in the formation of linear double chains along the b-axis direction.

Related literature

For the biological activities of substituted pyridine derivatives, see: Yao et al. (1994 ▶); Lohaus & Dittmar (1968 ▶). For a description of structure correlation, bond lengths and angles, see: Allen et al. (1987 ▶). For ring conformation parameters, see: Cremer & Pople (1975 ▶). The linearity of the cyano group seen in the title compound is typical of this class of 2-oxo­pyridine-3-carbo­nitrile compounds, see: Black et al. (1992 ▶); Hussain et al. (1996 ▶).

Experimental

Crystal data

C20H22N2O2

M = 322.40

Monoclinic,

a = 11.1652 (10) Å

b = 11.4205 (9) Å

c = 14.8540 (11) Å

β = 111.763 (2)°

V = 1759.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.29 × 0.25 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.981

23618 measured reflections

3266 independent reflections

2251 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.137

S = 1.05

3266 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814010332/gg2137sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010332/gg2137Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010332/gg2137Isup3.cml

CCDC reference: 1001458

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H22N2O2	F(000) = 688
Mr = 322.40	Dx = 1.217 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2000 reflections
a = 11.1652 (10) Å	θ = 2–26°
b = 11.4205 (9) Å	µ = 0.08 mm−1
c = 14.8540 (11) Å	T = 293 K
β = 111.763 (2)°	Block, colourless
V = 1759.1 (2) Å3	0.30 × 0.29 × 0.25 mm
Z = 4

Bruker Kappa APEXII diffractometer	3266 independent reflections
Radiation source: fine-focus sealed tube	2251 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 0 pixels mm-1	θmax = 25.5°, θmin = 2.3°
ω and φ scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.977, Tmax = 0.981	l = −17→17
23618 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0486P)2 + 0.8085P] where P = (Fo2 + 2Fc2)/3
3266 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 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
C1	0.13770 (18)	0.36565 (16)	0.23039 (14)	0.0433 (5)
C2	0.2136 (2)	0.47203 (18)	0.22349 (17)	0.0564 (6)
H2A	0.2578	0.4544	0.1798	0.068*
H2B	0.2790	0.4871	0.2870	0.068*
C3	0.1343 (2)	0.58356 (19)	0.18823 (16)	0.0601 (6)
H3A	0.1858	0.6383	0.1679	0.072*
H3B	0.0594	0.5639	0.1313	0.072*
C4	0.0876 (2)	0.64636 (19)	0.25967 (17)	0.0629 (6)
H4A	0.1615	0.6598	0.3190	0.075*
H4B	0.0545	0.7224	0.2328	0.075*
C5	−0.0158 (2)	0.5844 (2)	0.28588 (18)	0.0645 (6)
H5A	−0.0783	0.6423	0.2879	0.077*
H5B	−0.0604	0.5297	0.2343	0.077*
C6	0.0304 (3)	0.5184 (2)	0.38079 (17)	0.0655 (6)
H6A	−0.0430	0.4790	0.3873	0.079*
H6B	0.0624	0.5746	0.4332	0.079*
C7	0.1354 (2)	0.42796 (19)	0.39301 (15)	0.0574 (6)
H7A	0.2147	0.4683	0.3998	0.069*
H7B	0.1505	0.3844	0.4523	0.069*
C8	0.10287 (18)	0.34305 (16)	0.30965 (13)	0.0424 (4)
C9	0.03020 (18)	0.24227 (16)	0.30695 (13)	0.0407 (4)
C10	−0.00175 (18)	0.16888 (16)	0.22689 (13)	0.0413 (4)
C11	0.03687 (18)	0.20046 (16)	0.15077 (13)	0.0419 (5)
C12	−0.0716 (2)	0.06187 (19)	0.22081 (15)	0.0559 (6)
C13	0.0307 (3)	0.1604 (2)	−0.00811 (16)	0.0795 (8)
H13A	−0.0003	0.1013	−0.0574	0.119*
H13B	0.1223	0.1683	0.0108	0.119*
H13C	−0.0102	0.2337	−0.0330	0.119*
C91	−0.0182 (2)	0.21394 (17)	0.38544 (15)	0.0506 (5)
C92	−0.1455 (3)	0.2350 (2)	0.3709 (2)	0.0728 (7)
H92	−0.2006	0.2661	0.3124	0.087*
C93	−0.1909 (4)	0.2101 (3)	0.4427 (4)	0.1232 (16)
H93	−0.2770	0.2239	0.4327	0.148*
C94	−0.1098 (7)	0.1649 (3)	0.5291 (4)	0.140 (2)
H94	−0.1412	0.1487	0.5776	0.167*
C95	0.0175 (5)	0.1433 (3)	0.5450 (2)	0.1061 (13)
H95	0.0724	0.1130	0.6040	0.127*
C96	0.0628 (3)	0.1673 (2)	0.47174 (16)	0.0682 (7)
C97	0.2778 (4)	0.1043 (3)	0.5663 (2)	0.1477 (19)
H97A	0.3596	0.0935	0.5599	0.222*
H97B	0.2485	0.0308	0.5818	0.222*
H97C	0.2871	0.1596	0.6171	0.222*
N1	0.10398 (15)	0.29525 (13)	0.15152 (11)	0.0449 (4)
N2	−0.1246 (3)	−0.0247 (2)	0.21553 (17)	0.0915 (8)
O1	0.00127 (16)	0.12727 (12)	0.07402 (10)	0.0586 (4)
O2	0.1868 (2)	0.14718 (16)	0.47771 (13)	0.0875 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0415 (11)	0.0372 (10)	0.0509 (11)	−0.0009 (8)	0.0167 (9)	0.0006 (9)
C2	0.0571 (13)	0.0514 (13)	0.0674 (14)	−0.0139 (10)	0.0309 (11)	−0.0060 (11)
C3	0.0770 (16)	0.0461 (12)	0.0592 (13)	−0.0144 (11)	0.0276 (12)	0.0010 (10)
C4	0.0774 (16)	0.0416 (12)	0.0674 (15)	−0.0042 (11)	0.0244 (12)	−0.0003 (11)
C5	0.0678 (15)	0.0527 (13)	0.0741 (16)	0.0009 (11)	0.0275 (13)	−0.0095 (12)
C6	0.0912 (18)	0.0495 (13)	0.0666 (15)	−0.0145 (12)	0.0418 (13)	−0.0169 (11)
C7	0.0752 (15)	0.0499 (12)	0.0419 (11)	−0.0153 (11)	0.0155 (10)	−0.0025 (9)
C8	0.0453 (11)	0.0368 (10)	0.0417 (10)	−0.0017 (8)	0.0121 (9)	0.0003 (8)
C9	0.0440 (10)	0.0351 (9)	0.0429 (10)	0.0029 (8)	0.0159 (8)	0.0036 (8)
C10	0.0470 (11)	0.0329 (9)	0.0451 (10)	0.0001 (8)	0.0182 (9)	0.0026 (8)
C11	0.0489 (11)	0.0338 (10)	0.0431 (10)	0.0033 (8)	0.0172 (9)	−0.0002 (8)
C12	0.0764 (15)	0.0459 (12)	0.0517 (12)	−0.0099 (11)	0.0309 (11)	−0.0051 (10)
C13	0.137 (2)	0.0623 (15)	0.0528 (13)	−0.0205 (16)	0.0502 (15)	−0.0071 (12)
C91	0.0692 (14)	0.0376 (10)	0.0517 (12)	−0.0090 (10)	0.0300 (11)	−0.0072 (9)
C92	0.0771 (17)	0.0589 (15)	0.103 (2)	−0.0064 (13)	0.0573 (16)	−0.0143 (14)
C93	0.164 (4)	0.089 (2)	0.191 (4)	−0.038 (2)	0.151 (4)	−0.050 (3)
C94	0.277 (7)	0.083 (2)	0.139 (4)	−0.083 (3)	0.171 (5)	−0.056 (2)
C95	0.214 (4)	0.0631 (18)	0.0604 (16)	−0.058 (2)	0.074 (2)	−0.0173 (13)
C96	0.107 (2)	0.0470 (13)	0.0490 (13)	−0.0246 (13)	0.0276 (14)	−0.0059 (11)
C97	0.147 (3)	0.098 (2)	0.105 (3)	−0.044 (2)	−0.061 (2)	0.048 (2)
N1	0.0512 (10)	0.0376 (9)	0.0501 (9)	0.0003 (7)	0.0237 (8)	0.0013 (7)
N2	0.133 (2)	0.0638 (14)	0.0897 (16)	−0.0438 (14)	0.0552 (15)	−0.0150 (12)
O1	0.0903 (11)	0.0440 (8)	0.0488 (8)	−0.0127 (8)	0.0342 (8)	−0.0068 (7)
O2	0.0884 (14)	0.0793 (13)	0.0679 (11)	−0.0022 (10)	−0.0025 (10)	0.0277 (9)

C1—N1	1.354 (2)	C10—C11	1.399 (3)
C1—C2	1.506 (3)	C10—C12	1.434 (3)
C1—C8	1.394 (3)	C11—N1	1.314 (2)
C2—C3	1.529 (3)	C11—O1	1.349 (2)
C2—H2A	0.9700	C12—N2	1.140 (3)
C2—H2B	0.9700	C13—O1	1.427 (3)
C3—C4	1.524 (3)	C13—H13A	0.9600
C3—H3A	0.9700	C13—H13B	0.9600
C3—H3B	0.9700	C13—H13C	0.9600
C4—C5	1.523 (3)	C91—C96	1.373 (3)
C4—H4A	0.9700	C91—C92	1.377 (3)
C4—H4B	0.9700	C92—C93	1.370 (4)
C5—C6	1.511 (3)	C92—H92	0.9300
C5—H5A	0.9700	C93—C94	1.368 (6)
C5—H5B	0.9700	C93—H93	0.9300
C6—C7	1.522 (3)	C94—C95	1.374 (6)
C6—H6A	0.9700	C94—H94	0.9300
C6—H6B	0.9700	C95—C96	1.387 (4)
C7—C8	1.507 (3)	C95—H95	0.9300
C7—H7A	0.9700	C96—O2	1.373 (3)
C7—H7B	0.9700	C97—O2	1.418 (3)
C8—C9	1.400 (3)	C97—H97A	0.9600
C9—C10	1.389 (3)	C97—H97B	0.9600
C9—C91	1.491 (3)	C97—H97C	0.9600
N1—C1—C8	123.06 (17)	C10—C9—C91	119.08 (16)
N1—C1—C2	113.77 (17)	C8—C9—C91	122.01 (17)
C8—C1—C2	123.16 (18)	C9—C10—C11	118.57 (17)
C1—C2—C3	115.23 (18)	C9—C10—C12	121.95 (17)
C1—C2—H2A	108.5	C11—C10—C12	119.48 (17)
C3—C2—H2A	108.5	N1—C11—O1	120.39 (17)
C1—C2—H2B	108.5	N1—C11—C10	123.46 (17)
C3—C2—H2B	108.5	O1—C11—C10	116.15 (16)
H2A—C2—H2B	107.5	N2—C12—C10	178.3 (3)
C4—C3—C2	117.25 (19)	O1—C13—H13A	109.5
C4—C3—H3A	108.0	O1—C13—H13B	109.5
C2—C3—H3A	108.0	H13A—C13—H13B	109.5
C4—C3—H3B	108.0	O1—C13—H13C	109.5
C2—C3—H3B	108.0	H13A—C13—H13C	109.5
H3A—C3—H3B	107.2	H13B—C13—H13C	109.5
C5—C4—C3	116.56 (19)	C96—C91—C92	119.9 (2)
C5—C4—H4A	108.2	C96—C91—C9	120.6 (2)
C3—C4—H4A	108.2	C92—C91—C9	119.5 (2)
C5—C4—H4B	108.2	C93—C92—C91	120.0 (3)
C3—C4—H4B	108.2	C93—C92—H92	120.0
H4A—C4—H4B	107.3	C91—C92—H92	120.0
C6—C5—C4	116.2 (2)	C94—C93—C92	120.0 (4)
C6—C5—H5A	108.2	C94—C93—H93	120.0
C4—C5—H5A	108.2	C92—C93—H93	120.0
C6—C5—H5B	108.2	C93—C94—C95	120.8 (3)
C4—C5—H5B	108.2	C93—C94—H94	119.6
H5A—C5—H5B	107.4	C95—C94—H94	119.6
C5—C6—C7	115.56 (19)	C94—C95—C96	119.0 (4)
C5—C6—H6A	108.4	C94—C95—H95	120.5
C7—C6—H6A	108.4	C96—C95—H95	120.5
C5—C6—H6B	108.4	O2—C96—C91	115.1 (2)
C7—C6—H6B	108.4	O2—C96—C95	124.7 (3)
H6A—C6—H6B	107.5	C91—C96—C95	120.2 (3)
C8—C7—C6	113.47 (18)	O2—C97—H97A	109.5
C8—C7—H7A	108.9	O2—C97—H97B	109.5
C6—C7—H7A	108.9	H97A—C97—H97B	109.5
C8—C7—H7B	108.9	O2—C97—H97C	109.5
C6—C7—H7B	108.9	H97A—C97—H97C	109.5
H7A—C7—H7B	107.7	H97B—C97—H97C	109.5
C1—C8—C9	117.91 (17)	C11—N1—C1	118.11 (16)
C1—C8—C7	121.13 (17)	C11—O1—C13	117.98 (16)
C9—C8—C7	120.86 (17)	C96—O2—C97	118.4 (3)
C10—C9—C8	118.87 (17)
N1—C1—C2—C3	96.0 (2)	C12—C10—C11—O1	1.8 (3)
C8—C1—C2—C3	−82.6 (3)	C10—C9—C91—C96	104.5 (2)
C1—C2—C3—C4	74.9 (3)	C8—C9—C91—C96	−78.0 (3)
C2—C3—C4—C5	−69.3 (3)	C10—C9—C91—C92	−75.5 (2)
C3—C4—C5—C6	99.4 (2)	C8—C9—C91—C92	102.0 (2)
C4—C5—C6—C7	−54.6 (3)	C96—C91—C92—C93	0.4 (3)
C5—C6—C7—C8	−51.8 (3)	C9—C91—C92—C93	−179.6 (2)
N1—C1—C8—C9	0.3 (3)	C91—C92—C93—C94	0.4 (5)
C2—C1—C8—C9	178.87 (18)	C92—C93—C94—C95	−0.4 (5)
N1—C1—C8—C7	−176.05 (18)	C93—C94—C95—C96	−0.4 (5)
C2—C1—C8—C7	2.5 (3)	C92—C91—C96—O2	178.5 (2)
C6—C7—C8—C1	90.8 (2)	C9—C91—C96—O2	−1.5 (3)
C6—C7—C8—C9	−85.4 (2)	C92—C91—C96—C95	−1.2 (3)
C1—C8—C9—C10	1.1 (3)	C9—C91—C96—C95	178.8 (2)
C7—C8—C9—C10	177.50 (18)	C94—C95—C96—O2	−178.5 (3)
C1—C8—C9—C91	−176.42 (18)	C94—C95—C96—C91	1.2 (4)
C7—C8—C9—C91	0.0 (3)	O1—C11—N1—C1	−179.78 (17)
C8—C9—C10—C11	−1.8 (3)	C10—C11—N1—C1	0.2 (3)
C91—C9—C10—C11	175.77 (18)	C8—C1—N1—C11	−1.0 (3)
C8—C9—C10—C12	177.52 (19)	C2—C1—N1—C11	−179.66 (17)
C91—C9—C10—C12	−4.9 (3)	N1—C11—O1—C13	−4.4 (3)
C9—C10—C11—N1	1.2 (3)	C10—C11—O1—C13	175.6 (2)
C12—C10—C11—N1	−178.16 (19)	C91—C96—O2—C97	177.0 (2)
C9—C10—C11—O1	−178.80 (16)	C95—C96—O2—C97	−3.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg1i	0.97	2.64	3.742 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg1i	0.97	2.64	3.742 (2)	134

Symmetry code: (i) .