5-(4-Chloro­phen­yl)-1-methyl-3-oxocyclo­hexa­necarbonitrile

Mohan, R.T.S.; Kamatchi, S.; Subramanyam, M.; Thiruvalluvar, A.; Linden, A.

doi:10.1107/S1600536808012816

organic compounds

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Volume 64| Part 6| June 2008| Page o1006

doi:10.1107/S1600536808012816

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5-(4-Chlorophenyl)-1-methyl-3-oxocyclohexanecarbonitrile

R. T. Sabapathy Mohan,^a S. Kamatchi,^a M. Subramanyam,^b A. Thiruvalluvar ^b ^* and A. Linden ^c

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India, ^bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, and ^cInstitute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
^*Correspondence e-mail: athiru@vsnl.net

(Received 3 April 2008; accepted 30 April 2008; online 7 May 2008)

In the title molecule, C₁₄H₁₄ClNO, the cyclohexane ring adopts a chair conformation. The cyano group and the methyl group have axial and equatorial orientations, respectively. The benzene ring has an equatorial orientation. A C—H⋯π interaction involving the benzene ring is found in the crystal structure.

Related literature

Experimental

Crystal data

C₁₄H₁₄ClNO
M_r = 247.71
Monoclinic, C 2/c
a = 23.3358 (6) Å
b = 6.0031 (2) Å
c = 20.8948 (6) Å
β = 122.386 (2)°
V = 2471.81 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 160 (1) K
0.28 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.877, T_max = 0.956
28232 measured reflections
2822 independent reflections
2211 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.05
2822 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯Cgⁱ	0.99	2.60	3.5333 (18)	157
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ . Cg is the centroid of the benzene ring.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012816/ww2118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012816/ww2118Isup2.hkl

checkCIF report

Comment top

Subramanyam et al. (2007a,b) and Thiruvalluvar et al. (2007) have reported the crystal structures of substituted cyclohexane derivatives, in which the cyclohexane rings are in chair conformation. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The cyclohexane ring adopts a chair conformation. The cyano group and the methyl group at position 1 have axial and equatorial orientations respectively. The benzene ring at position 5 has an equatorial orientation. A C4—H4B···π(-x, y, 1/2 - z) interaction involving the benzene ring is found in the structure. No classical hydrogen bonds are found in the crystal structure.

Related literature top

Experimental top

A mixture of 5–4'-chlorophenyl-3-methylcyclohex-2-enone (6.40 g, 0.02 mol), potassium cyanide (2.60 g, 0.04 mol), ammonium chloride (1.59 g, 0.03 mol), dimethyl formamide (50 ml) and water (2 ml) was heated with stirring for 16–18 h at 353 K. The reaction mixture was cooled to room temperature and poured into water. The product was extracted with CH₂Cl₂ (3x10 ml) and the organic layer was dried, evaporated and purified by column chromatography (hexane-EtOAc, 4.5:1 v/v). The yield of the isolated product was 4.30 g (87%).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are represented by spheres of arbitrary radius.

5-(4-Chlorophenyl)-1-methyl-3-oxocyclohexanecarbonitrile top

Crystal data top

C₁₄H₁₄ClNO	F(000) = 1040
M_r = 247.71	D_x = 1.331 Mg m⁻³
Monoclinic, C2/c	Melting point: 358 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 23.3358 (6) Å	Cell parameters from 31960 reflections
b = 6.0031 (2) Å	θ = 2.0–27.5°
c = 20.8948 (6) Å	µ = 0.29 mm⁻¹
β = 122.386 (2)°	T = 160 K
V = 2471.81 (14) Å³	Prism, colourless
Z = 8	0.28 × 0.20 × 0.18 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	2822 independent reflections
Radiation source: Nonius FR590 sealed tube generator	2211 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.058
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
ϕ and ω scans with κ offsets	h = −30→29
Absorption correction: multi-scan (Blessing, 1995)	k = −7→7
T_min = 0.877, T_max = 0.956	l = −27→27
28232 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0525P)² + 1.7764P] where P = (F_o² + 2F_c²)/3
2822 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₄H₁₄ClNO	V = 2471.81 (14) Å³
M_r = 247.71	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.3358 (6) Å	µ = 0.29 mm⁻¹
b = 6.0031 (2) Å	T = 160 K
c = 20.8948 (6) Å	0.28 × 0.20 × 0.18 mm
β = 122.386 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2822 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	2211 reflections with I > 2σ(I)
T_min = 0.877, T_max = 0.956	R_int = 0.058
28232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
2822 reflections	Δρ_min = −0.32 e Å⁻³
154 parameters

Special details top

Experimental. Cooling Device: Oxford Cryosystems Cryostream 700

Crystal mount: glued on a glass fibre

Mosaicity (°.): 0.793 (2)

Frames collected: 394

Seconds exposure per frame: 16

Degrees rotation per frame: 1.6

Crystal-Detector distance (mm): 30.0

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl1	−0.25175 (2)	0.41436 (8)	0.08818 (3)	0.0406 (2)
O3	0.15529 (6)	1.0355 (2)	0.24871 (7)	0.0401 (4)
N12	0.08284 (8)	0.8728 (3)	0.02081 (8)	0.0387 (5)
C1	0.12125 (8)	0.5713 (3)	0.12750 (9)	0.0257 (5)
C2	0.16797 (8)	0.6816 (3)	0.20566 (9)	0.0296 (5)
C3	0.13140 (8)	0.8524 (3)	0.22416 (9)	0.0290 (5)
C4	0.06351 (8)	0.7819 (3)	0.21034 (9)	0.0292 (5)
C5	0.01764 (7)	0.6715 (3)	0.13228 (8)	0.0241 (4)
C6	0.05647 (8)	0.4842 (3)	0.12188 (9)	0.0264 (5)
C11	0.15935 (9)	0.3848 (3)	0.11531 (10)	0.0350 (5)
C12	0.10064 (8)	0.7426 (3)	0.06780 (9)	0.0277 (5)
C51	−0.04910 (7)	0.6001 (3)	0.12231 (8)	0.0239 (4)
C52	−0.10261 (8)	0.7514 (3)	0.09191 (8)	0.0270 (5)
C53	−0.16454 (8)	0.6975 (3)	0.08277 (9)	0.0293 (5)
C54	−0.17302 (8)	0.4867 (3)	0.10337 (9)	0.0289 (5)
C55	−0.12083 (9)	0.3334 (3)	0.13444 (10)	0.0322 (5)
C56	−0.05897 (8)	0.3916 (3)	0.14389 (10)	0.0304 (5)
H2A	0.18685	0.56475	0.24527	0.0355*
H2B	0.20638	0.75446	0.20642	0.0355*
H4A	0.04006	0.91413	0.21396	0.0350*
H4B	0.07101	0.67576	0.25040	0.0350*
H5	0.00699	0.78708	0.09293	0.0289*
H6A	0.02664	0.41375	0.07173	0.0316*
H6B	0.06906	0.36910	0.16120	0.0316*
H11A	0.17294	0.27012	0.15427	0.0524*
H11B	0.19981	0.44642	0.11878	0.0524*
H11C	0.12964	0.31858	0.06508	0.0524*
H52	−0.09668	0.89480	0.07705	0.0325*
H53	−0.20035	0.80334	0.06276	0.0353*
H55	−0.12702	0.19013	0.14917	0.0386*
H56	−0.02282	0.28695	0.16550	0.0365*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0277 (2)	0.0501 (3)	0.0477 (3)	−0.0075 (2)	0.0227 (2)	0.0017 (2)
O3	0.0388 (7)	0.0398 (7)	0.0447 (7)	−0.0129 (6)	0.0243 (6)	−0.0142 (6)
N12	0.0368 (8)	0.0456 (9)	0.0359 (8)	−0.0065 (7)	0.0210 (7)	0.0043 (7)
C1	0.0237 (8)	0.0280 (8)	0.0280 (8)	−0.0011 (6)	0.0156 (7)	−0.0011 (6)
C2	0.0240 (8)	0.0357 (9)	0.0279 (8)	−0.0012 (7)	0.0131 (7)	−0.0017 (7)
C3	0.0287 (8)	0.0343 (9)	0.0220 (7)	−0.0040 (7)	0.0122 (7)	−0.0022 (7)
C4	0.0299 (8)	0.0316 (9)	0.0297 (8)	−0.0017 (7)	0.0184 (7)	−0.0036 (7)
C5	0.0242 (7)	0.0249 (8)	0.0253 (7)	−0.0005 (6)	0.0146 (6)	0.0019 (6)
C6	0.0257 (8)	0.0276 (8)	0.0287 (8)	−0.0037 (6)	0.0165 (7)	−0.0023 (7)
C11	0.0339 (9)	0.0342 (9)	0.0438 (10)	0.0003 (7)	0.0255 (8)	−0.0037 (8)
C12	0.0248 (8)	0.0338 (9)	0.0284 (8)	−0.0071 (7)	0.0169 (7)	−0.0056 (7)
C51	0.0239 (7)	0.0286 (8)	0.0215 (7)	−0.0019 (6)	0.0136 (6)	−0.0010 (6)
C52	0.0272 (8)	0.0285 (8)	0.0254 (8)	−0.0012 (7)	0.0141 (6)	0.0037 (6)
C53	0.0242 (8)	0.0352 (9)	0.0260 (8)	0.0019 (7)	0.0117 (7)	0.0038 (7)
C54	0.0240 (8)	0.0365 (9)	0.0276 (8)	−0.0071 (7)	0.0147 (7)	−0.0036 (7)
C55	0.0348 (9)	0.0265 (8)	0.0423 (10)	−0.0033 (7)	0.0254 (8)	0.0014 (7)
C56	0.0299 (8)	0.0273 (8)	0.0394 (9)	0.0032 (7)	0.0221 (8)	0.0047 (7)

Geometric parameters (Å, º) top

Cl1—C54	1.744 (2)	C54—C55	1.380 (3)
O3—C3	1.215 (2)	C55—C56	1.393 (3)
N12—C12	1.145 (2)	C2—H2A	0.9900
C1—C2	1.545 (2)	C2—H2B	0.9900
C1—C6	1.544 (3)	C4—H4A	0.9900
C1—C11	1.533 (3)	C4—H4B	0.9900
C1—C12	1.484 (2)	C5—H5	1.0000
C2—C3	1.511 (3)	C6—H6A	0.9900
C3—C4	1.511 (3)	C6—H6B	0.9900
C4—C5	1.541 (2)	C11—H11A	0.9800
C5—C6	1.531 (3)	C11—H11B	0.9800
C5—C51	1.518 (3)	C11—H11C	0.9800
C51—C52	1.392 (3)	C52—H52	0.9500
C51—C56	1.391 (3)	C53—H53	0.9500
C52—C53	1.391 (3)	C55—H55	0.9500
C53—C54	1.385 (3)	C56—H56	0.9500

Cl1···N12ⁱ	3.335 (2)	H4B···C51ⁱⁱ	3.0000
Cl1···C12ⁱ	3.397 (2)	H4B···C52ⁱⁱ	3.0000
Cl1···H2Aⁱⁱ	3.0900	H4B···C53ⁱⁱ	2.9600
O3···H6Bⁱⁱⁱ	2.7300	H4B···C54ⁱⁱ	2.9200
O3···H11Aⁱⁱⁱ	2.6300	H4B···C55ⁱⁱ	2.8900
O3···H55^iv	2.7100	H4B···C56ⁱⁱ	2.9200
N12···Cl1^v	3.335 (2)	H5···N12	2.9200
N12···H5	2.9200	H5···C12	2.5200
N12···H6A^vi	2.8200	H5···H52	2.3500
N12···H52^vii	2.6300	H6A···C56	3.0800
N12···H11Cⁱⁱⁱ	2.8500	H6A···H11C	2.5500
C4···C12	3.527 (3)	H6A···N12^vi	2.8200
C12···C4	3.527 (3)	H6A···C12^vi	2.9900
C12···Cl1^v	3.397 (2)	H6B···O3^ix	2.7300
C6···H56	2.7300	H6B···C56	2.8100
C12···H5	2.5200	H6B···H11A	2.5700
C12···H6A^vi	2.9900	H6B···H56	2.2500
C51···H4Bⁱⁱ	3.0000	H11A···O3^ix	2.6300
C52···H4A	3.0700	H11A···H2A	2.4900
C52···H55ⁱⁱⁱ	3.0700	H11A···H6B	2.5700
C52···H4Bⁱⁱ	3.0000	H11B···H2B	2.5500
C52···H11C^vi	3.0200	H11C···N12^ix	2.8500
C53···H4Bⁱⁱ	2.9600	H11C···H6A	2.5500
C53···H53^viii	2.9900	H11C···C52^vi	3.0200
C54···H4Bⁱⁱ	2.9200	H52···C55ⁱⁱⁱ	3.0700
C55···H52^ix	3.0700	H52···H5	2.3500
C55···H4Bⁱⁱ	2.8900	H52···N12^vii	2.6300
C56···H6A	3.0800	H53···C53^viii	2.9900
C56···H6B	2.8100	H53···H53^viii	2.4800
C56···H4Bⁱⁱ	2.9200	H55···C52^ix	3.0700
H2A···H11A	2.4900	H55···O3^x	2.7100
H2A···Cl1ⁱⁱ	3.0900	H56···C6	2.7300
H2B···H11B	2.5500	H56···H4A^ix	2.5700
H4A···C52	3.0700	H56···H6B	2.2500
H4A···H56ⁱⁱⁱ	2.5700

C2—C1—C6	109.48 (15)	C3—C2—H2B	109.00
C2—C1—C11	110.17 (15)	H2A—C2—H2B	108.00
C2—C1—C12	108.61 (15)	C3—C4—H4A	109.00
C6—C1—C11	111.80 (15)	C3—C4—H4B	109.00
C6—C1—C12	107.91 (15)	C5—C4—H4A	109.00
C11—C1—C12	108.79 (15)	C5—C4—H4B	109.00
C1—C2—C3	112.70 (16)	H4A—C4—H4B	108.00
O3—C3—C2	121.85 (19)	C4—C5—H5	107.00
O3—C3—C4	122.09 (18)	C6—C5—H5	107.00
C2—C3—C4	116.05 (15)	C51—C5—H5	107.00
C3—C4—C5	112.68 (15)	C1—C6—H6A	109.00
C4—C5—C6	109.74 (14)	C1—C6—H6B	109.00
C4—C5—C51	110.28 (14)	C5—C6—H6A	109.00
C6—C5—C51	114.51 (15)	C5—C6—H6B	109.00
C1—C6—C5	111.74 (15)	H6A—C6—H6B	108.00
N12—C12—C1	178.0 (2)	C1—C11—H11A	109.00
C5—C51—C52	118.81 (16)	C1—C11—H11B	109.00
C5—C51—C56	123.05 (16)	C1—C11—H11C	109.00
C52—C51—C56	118.12 (18)	H11A—C11—H11B	109.00
C51—C52—C53	121.54 (17)	H11A—C11—H11C	109.00
C52—C53—C54	118.75 (18)	H11B—C11—H11C	109.00
Cl1—C54—C53	118.89 (15)	C51—C52—H52	119.00
Cl1—C54—C55	119.86 (15)	C53—C52—H52	119.00
C53—C54—C55	121.2 (2)	C52—C53—H53	121.00
C54—C55—C56	119.07 (17)	C54—C53—H53	121.00
C51—C56—C55	121.26 (18)	C54—C55—H55	120.00
C1—C2—H2A	109.00	C56—C55—H55	120.00
C1—C2—H2B	109.00	C51—C56—H56	119.00
C3—C2—H2A	109.00	C55—C56—H56	119.00

C6—C1—C2—C3	−51.31 (19)	C4—C5—C51—C52	88.61 (17)
C11—C1—C2—C3	−174.65 (16)	C4—C5—C51—C56	−89.75 (19)
C12—C1—C2—C3	66.3 (2)	C6—C5—C51—C52	−147.05 (14)
C2—C1—C6—C5	58.91 (17)	C6—C5—C51—C56	34.6 (2)
C11—C1—C6—C5	−178.71 (13)	C5—C51—C52—C53	−178.71 (14)
C12—C1—C6—C5	−59.12 (17)	C56—C51—C52—C53	−0.3 (2)
C1—C2—C3—O3	−133.05 (17)	C5—C51—C56—C55	179.36 (15)
C1—C2—C3—C4	47.0 (2)	C52—C51—C56—C55	1.0 (2)
O3—C3—C4—C5	132.96 (17)	C51—C52—C53—C54	−1.1 (2)
C2—C3—C4—C5	−47.1 (2)	C52—C53—C54—Cl1	−177.24 (12)
C3—C4—C5—C6	51.79 (19)	C52—C53—C54—C55	1.8 (2)
C3—C4—C5—C51	178.83 (14)	Cl1—C54—C55—C56	177.93 (14)
C4—C5—C6—C1	−59.17 (18)	C53—C54—C55—C56	−1.1 (3)
C51—C5—C6—C1	176.20 (12)	C54—C55—C56—C51	−0.3 (3)

Symmetry codes: (i) x−1/2, y−1/2, z; (ii) −x, y, −z+1/2; (iii) x, y+1, z; (iv) −x, y+1, −z+1/2; (v) x+1/2, y+1/2, z; (vi) −x, −y+1, −z; (vii) −x, −y+2, −z; (viii) −x−1/2, −y+3/2, −z; (ix) x, y−1, z; (x) −x, y−1, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···Cgⁱⁱ	0.99	2.60	3.5333 (18)	157

Symmetry code: (ii) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄ClNO
M_r	247.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	160
a, b, c (Å)	23.3358 (6), 6.0031 (2), 20.8948 (6)
β (°)	122.386 (2)
V (Å³)	2471.81 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.28 × 0.20 × 0.18

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.877, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	28232, 2822, 2211
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.05
No. of reflections	2822
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···Cgⁱ	0.99	2.60	3.5333 (18)	157

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

AT thanks the UGC, India, for the award of a Minor Research Project [file No. MRP-2355/06 (UGC-SERO), link No. 2355, 10/01/2007].

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