2-Meth­oxy-4-(2-meth­oxy­phen­yl)-5,6,7,8,9,10-hexa­hydro­cyclo­octa­[b]pyridine-3-carbo­nitrile

Vishnupriya, R.; Suresh, J.; Maharani, S.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536814010332

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o656

doi:10.1107/S1600536814010332

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2-Methoxy-4-(2-methoxyphenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile

R. Vishnupriya,^a J. Suresh,^a S. Maharani,^b R. Ranjith Kumar ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

Edited by J. F. Gallagher, Dublin City University, Ireland (Received 15 March 2014; accepted 7 May 2014; online 10 May 2014)

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

CCDC reference: 1001458

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_r = 322.40
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.137
S = 1.05
3266 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

CCDC reference: 1001458

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814010332/gg2137sup1.cif

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

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

checkCIF report

Comment top

Pyridine derivatives have a wide range of biological activities being used as fungicidal, antibacterial, antifungal, antimycotic (Lohaus et al., 1968) and antidepressant agents, as well as thienopyridines being used as antithrombotic agents (Yao et al., 1994) against platelet aggregation. The above observations prompted us to synthesize the title compound containing pyridine carbonitrile groups and substitued pyridine scaffolds to determine its crystal structure.

The molecular structure of the title compound is shown in Fig 1. The cyclooctane ring (C1–C8) adopts a twisted boat chair conformation as evidenced by the puckering parameters q₂ = 1.1578 (8) Å, θ = 67.05 (2)°, ϕ = 103.05 (2)° (Cremer & Pople, 1975). The central pyridine component is planar, with a maximum deviation from the mean plane that of 0.0092 (1) Å for atom C10. The shortening of the C–N distances [1.354 (3) and 1.314 (3) Å] and the opening of the N1–C11–C10 angle [123.46 (2)°] may be attributed to the size of the substituent at C1. The sum of the C—N—C bond angle around N1 atom (365.0 (6)°) is implying a noticeable flattening of the trigonal pyramidal geometry about N1. The C10—C12 ≡N2 bond angle of 178.27 (1)° defining the linearity of the cyano group are typical of this group of 2-oxopyridine-3-carbonitrile compounds (Black et al., 1992; Hussain et al., 1996). The bond distances in the central pyridine ring range 1.314 (1) – 1.400 (2) Å suggest possible delocalization of the π electrons over the ring (Allen et al., 1987). The dihedral angle between the pseudo-axial phenyl substituent and the plane of the pyridine ring is 76.32 (8)°. Due to conjugation, the bond length C11—O1 ═1.349 (4) Å is shorter than the bond length C13—O1 ═ 1.427 (2) Å.

The molecular structure features a weak intermolecular C—H···Cg1 interaction between inverse related molecules forming a linear double chain along b axis. [symmetry code: (i) 1/2 - x, 1/2 + y, 1/2 - z](Fig 2)(Cg1 is the centroid of the pyridine ring N1/C1/C8–C11).

Related literature top

For the biological activities of substituted pyridine derivatives, see: (Yao et al., 1994); Lohaus et al.,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 2-oxopyridine-3-carbonitrile compounds, see: Black et al. (1992); Hussain et al. (1996).

Experimental top

Preparation: A mixture of cyclooctanone (1 mmol), 2-methoxy benzaldehyde (1 mmol) and malononitrile (1 mmol) were taken in methanol (10 ml) to which lithium ethoxide (1 equiv) was added. The reaction mixture was heated under reflux for 2–3 h. After completion of the reaction (TLC), the reaction mixture was poured into crushed ice and extracted with ethyl acetate. The excess solvent was removed under vacuum and the residue was subjected to column chromatography using petroleum ether/ ethyl acetate mixture (95:5 v/v) as eluent to obtain pure product. Melting point:151–156 °C, Yield: 71%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Partial packing view of the compound showing molecules interconnected through a C—H···π stacking interaction (dotted lines; symmetry code: (i) 1/2 - x, 1/2 + y, 1/2 - z)

2-Methoxy-4-(2-methoxyphenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile top

Crystal data top

C₂₀H₂₂N₂O₂	F(000) = 688
M_r = 322.40	D_x = 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

Data collection top

Bruker Kappa APEXII diffractometer	3266 independent reflections
Radiation source: fine-focus sealed tube	2251 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 0 pixels mm^-1	θ_max = 25.5°, θ_min = 2.3°
ω and ϕ scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.977, T_max = 0.981	l = −17→17
23618 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0486P)² + 0.8085P] where P = (F_o² + 2F_c²)/3
3266 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₀H₂₂N₂O₂	V = 1759.1 (2) Å³
M_r = 322.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.1652 (10) Å	µ = 0.08 mm⁻¹
b = 11.4205 (9) Å	T = 293 K
c = 14.8540 (11) Å	0.30 × 0.29 × 0.25 mm
β = 111.763 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	3266 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2251 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.981	R_int = 0.029
23618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
3266 reflections	Δρ_min = −0.29 e Å⁻³
217 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

JS and RV thank the management of the Madura College for their encouragement and support. RRK thanks the University Grants Commission, New Delhi, for funds through Major Research Project F. No. 42–242/2013 (SR)

References

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

2-Meth­­oxy-4-(2-meth­­oxy­phen­yl)-5,6,7,8,9,10-hexa­hydro­cyclo­octa­[b]pyridine-3-carbo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Methoxy-4-(2-methoxyphenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile