(4RS)-Methyl 4-cyano-4-cyclo-hexyl-4-phenyl-butano-ate.

In the crystal structure of the title compound, C(18)H(23)NO(2), there are only van der Waals inter-actions present. The cyclo-hexyl ring has a chair conformation. The longer axes of the displacement parameters of the non-H atoms forming the ethyl-methyl-carboxyl-ate skeleton are perpendicular to the plane through the non-H atoms of this skeleton.

Related literature

For general background to pharmaceutical applications of methyl 4-cyano-4-cyclo­hexyl-4-phenyl­butano­ates, see: Hartmann & Batzl (1986 ▶), Hartmann et al. (1992 ▶); Fadel & Garcia-Argote (1996 ▶).

Experimental

Crystal data

C18H23NO2

M = 285.37

Monoclinic,

a = 8.877 (6) Å

b = 9.120 (6) Å

c = 20.690 (14) Å

β = 95.769 (6)°

V = 1666.5 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.983, T max = 0.986

13440 measured reflections

3816 independent reflections

2026 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.153

S = 1.06

3816 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021320/fb2251sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021320/fb2251Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021320/fb2251Isup3.cml

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

C18H23NO2	F(000) = 616
Mr = 285.37	Dx = 1.137 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2935 reflections
a = 8.877 (6) Å	θ = 2.4–24.9°
b = 9.120 (6) Å	µ = 0.07 mm−1
c = 20.690 (14) Å	T = 296 K
β = 95.769 (6)°	Block, colourless
V = 1666.5 (19) Å3	0.23 × 0.21 × 0.19 mm
Z = 4

Bruker APEXII CCD diffractometer	3816 independent reflections
Radiation source: fine-focus sealed tube	2026 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −11→11
Tmin = 0.983, Tmax = 0.986	k = −10→11
13440 measured reflections	l = −26→26

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.0382P)2 + 0.7938P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3816 reflections	Δρmax = 0.24 e Å−3
192 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
91 constraints	Extinction coefficient: 0.0181 (18)
Primary atom site location: structure-invariant direct methods

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	0.2736 (3)	0.2805 (2)	0.70020 (10)	0.0531 (6)
H1	0.3761	0.2581	0.7018	0.064*
C2	0.1862 (3)	0.2158 (3)	0.74406 (11)	0.0652 (7)
H2	0.2305	0.1505	0.7748	0.078*
C3	0.0358 (3)	0.2470 (3)	0.74258 (12)	0.0666 (7)
H3	−0.0221	0.2035	0.7723	0.080*
C4	−0.0298 (3)	0.3430 (3)	0.69695 (12)	0.0613 (6)
H4	−0.1326	0.3639	0.6956	0.074*
C5	0.0566 (2)	0.4086 (3)	0.65311 (11)	0.0537 (6)
H5	0.0116	0.4740	0.6225	0.064*
C6	0.2101 (2)	0.3778 (2)	0.65421 (9)	0.0431 (5)
C7	0.3020 (2)	0.4512 (2)	0.60391 (9)	0.0438 (5)
C8	0.3038 (2)	0.6215 (2)	0.61212 (10)	0.0478 (5)
H8	0.1991	0.6555	0.6031	0.057*
C9	0.3583 (3)	0.6683 (2)	0.68142 (10)	0.0539 (6)
H9A	0.2947	0.6233	0.7113	0.065*
H9B	0.4611	0.6339	0.6924	0.065*
C10	0.3539 (3)	0.8345 (3)	0.68922 (12)	0.0664 (7)
H10A	0.2500	0.8681	0.6819	0.080*
H10B	0.3924	0.8605	0.7333	0.080*
C11	0.4475 (3)	0.9097 (3)	0.64200 (15)	0.0814 (8)
H11A	0.4389	1.0152	0.6465	0.098*
H11B	0.5532	0.8832	0.6517	0.098*
C12	0.3937 (4)	0.8653 (3)	0.57336 (14)	0.0828 (9)
H12A	0.4576	0.9109	0.5437	0.099*
H12B	0.2911	0.9004	0.5625	0.099*
C13	0.3972 (3)	0.6996 (3)	0.56456 (12)	0.0712 (8)
H13A	0.5011	0.6656	0.5712	0.085*
H13B	0.3576	0.6751	0.5205	0.085*
C14	0.4603 (3)	0.3992 (3)	0.61248 (10)	0.0525 (6)
C15	0.2354 (3)	0.4061 (2)	0.53446 (10)	0.0519 (6)
H15A	0.1331	0.4440	0.5265	0.062*
H15B	0.2954	0.4507	0.5031	0.062*
C16	0.2321 (3)	0.2420 (3)	0.52422 (11)	0.0638 (7)
H16A	0.3351	0.2051	0.5299	0.077*
H16B	0.1773	0.1972	0.5574	0.077*
C17	0.1604 (3)	0.1957 (3)	0.45895 (11)	0.0600 (6)
C18	0.1176 (4)	−0.0077 (4)	0.38785 (14)	0.1048 (11)
H18A	0.1542	0.0453	0.3525	0.157*
H18B	0.0091	−0.0021	0.3846	0.157*
H18C	0.1481	−0.1085	0.3860	0.157*
N1	0.5830 (3)	0.3602 (3)	0.61735 (10)	0.0782 (7)
O1	0.0970 (3)	0.2726 (2)	0.41959 (11)	0.1196 (9)
O2	0.1799 (3)	0.0558 (2)	0.44876 (9)	0.0983 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0528 (13)	0.0558 (14)	0.0509 (12)	0.0029 (11)	0.0056 (10)	0.0068 (11)
C2	0.0753 (18)	0.0634 (17)	0.0575 (14)	−0.0026 (14)	0.0097 (12)	0.0161 (12)
C3	0.0739 (18)	0.0654 (17)	0.0638 (15)	−0.0129 (14)	0.0233 (13)	0.0035 (13)
C4	0.0519 (14)	0.0630 (16)	0.0714 (16)	−0.0043 (12)	0.0185 (12)	−0.0075 (13)
C5	0.0542 (14)	0.0514 (14)	0.0556 (13)	0.0078 (11)	0.0065 (10)	0.0024 (11)
C6	0.0487 (12)	0.0408 (12)	0.0401 (10)	0.0021 (9)	0.0063 (9)	−0.0015 (9)
C7	0.0475 (12)	0.0452 (13)	0.0393 (10)	0.0096 (10)	0.0066 (9)	0.0034 (9)
C8	0.0526 (13)	0.0461 (13)	0.0456 (11)	0.0047 (10)	0.0086 (9)	0.0050 (10)
C9	0.0567 (14)	0.0526 (14)	0.0534 (13)	−0.0002 (11)	0.0096 (10)	0.0007 (11)
C10	0.0753 (17)	0.0576 (16)	0.0672 (16)	0.0004 (13)	0.0113 (13)	−0.0077 (13)
C11	0.095 (2)	0.0509 (16)	0.101 (2)	−0.0073 (15)	0.0258 (17)	−0.0033 (15)
C12	0.115 (2)	0.0532 (17)	0.085 (2)	−0.0024 (16)	0.0358 (17)	0.0148 (15)
C13	0.101 (2)	0.0556 (16)	0.0617 (15)	−0.0003 (14)	0.0320 (14)	0.0084 (12)
C14	0.0559 (14)	0.0576 (15)	0.0452 (12)	0.0075 (12)	0.0116 (10)	0.0051 (10)
C15	0.0653 (14)	0.0503 (14)	0.0398 (11)	0.0109 (11)	0.0045 (10)	0.0034 (10)
C16	0.0911 (19)	0.0530 (15)	0.0457 (12)	0.0089 (13)	−0.0007 (12)	0.0013 (11)
C17	0.0696 (16)	0.0571 (16)	0.0514 (13)	0.0059 (13)	−0.0031 (11)	0.0007 (12)
C18	0.143 (3)	0.085 (2)	0.081 (2)	−0.026 (2)	−0.0188 (19)	−0.0271 (18)
N1	0.0605 (14)	0.0992 (19)	0.0761 (15)	0.0187 (13)	0.0131 (11)	0.0069 (13)
O1	0.175 (2)	0.0836 (16)	0.0866 (15)	0.0319 (15)	−0.0539 (15)	−0.0107 (12)
O2	0.158 (2)	0.0592 (13)	0.0704 (12)	0.0056 (12)	−0.0256 (12)	−0.0117 (10)

C1—C6	1.379 (3)	C10—H10B	0.9700
C1—C2	1.384 (3)	C11—C12	1.508 (4)
C1—H1	0.9300	C11—H11A	0.9700
C2—C3	1.362 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—C13	1.523 (4)
C3—C4	1.374 (4)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.382 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.389 (3)	C14—N1	1.140 (3)
C5—H5	0.9300	C15—C16	1.512 (3)
C6—C7	1.538 (3)	C15—H15A	0.9700
C7—C14	1.477 (3)	C15—H15B	0.9700
C7—C15	1.553 (3)	C16—C17	1.495 (3)
C7—C8	1.562 (3)	C16—H16A	0.9700
C8—C13	1.525 (3)	C16—H16B	0.9700
C8—C9	1.528 (3)	C17—O1	1.174 (3)
C8—H8	0.9800	C17—O2	1.308 (3)
C9—C10	1.525 (3)	C18—O2	1.445 (3)
C9—H9A	0.9700	C18—H18A	0.9600
C9—H9B	0.9700	C18—H18B	0.9600
C10—C11	1.510 (4)	C18—H18C	0.9600
C10—H10A	0.9700
C6—C1—C2	120.6 (2)	C12—C11—C10	110.1 (2)
C6—C1—H1	119.7	C12—C11—H11A	109.6
C2—C1—H1	119.7	C10—C11—H11A	109.6
C3—C2—C1	120.6 (2)	C12—C11—H11B	109.6
C3—C2—H2	119.7	C10—C11—H11B	109.6
C1—C2—H2	119.7	H11A—C11—H11B	108.1
C2—C3—C4	119.7 (2)	C11—C12—C13	111.8 (2)
C2—C3—H3	120.1	C11—C12—H12A	109.3
C4—C3—H3	120.1	C13—C12—H12A	109.3
C3—C4—C5	120.1 (2)	C11—C12—H12B	109.3
C3—C4—H4	119.9	C13—C12—H12B	109.3
C5—C4—H4	119.9	H12A—C12—H12B	107.9
C4—C5—C6	120.7 (2)	C12—C13—C8	111.6 (2)
C4—C5—H5	119.7	C12—C13—H13A	109.3
C6—C5—H5	119.7	C8—C13—H13A	109.3
C1—C6—C5	118.2 (2)	C12—C13—H13B	109.3
C1—C6—C7	122.61 (19)	C8—C13—H13B	109.3
C5—C6—C7	119.14 (18)	H13A—C13—H13B	108.0
C14—C7—C6	110.00 (17)	N1—C14—C7	178.1 (2)
C14—C7—C15	107.19 (17)	C16—C15—C7	113.07 (17)
C6—C7—C15	109.40 (18)	C16—C15—H15A	109.0
C14—C7—C8	107.87 (18)	C7—C15—H15A	109.0
C6—C7—C8	111.05 (16)	C16—C15—H15B	109.0
C15—C7—C8	111.26 (16)	C7—C15—H15B	109.0
C13—C8—C9	109.49 (19)	H15A—C15—H15B	107.8
C13—C8—C7	113.23 (18)	C17—C16—C15	113.97 (19)
C9—C8—C7	112.28 (17)	C17—C16—H16A	108.8
C13—C8—H8	107.2	C15—C16—H16A	108.8
C9—C8—H8	107.2	C17—C16—H16B	108.8
C7—C8—H8	107.2	C15—C16—H16B	108.8
C10—C9—C8	111.61 (19)	H16A—C16—H16B	107.7
C10—C9—H9A	109.3	O1—C17—O2	122.2 (2)
C8—C9—H9A	109.3	O1—C17—C16	126.1 (2)
C10—C9—H9B	109.3	O2—C17—C16	111.7 (2)
C8—C9—H9B	109.3	O2—C18—H18A	109.5
H9A—C9—H9B	108.0	O2—C18—H18B	109.5
C11—C10—C9	111.2 (2)	H18A—C18—H18B	109.5
C11—C10—H10A	109.4	O2—C18—H18C	109.5
C9—C10—H10A	109.4	H18A—C18—H18C	109.5
C11—C10—H10B	109.4	H18B—C18—H18C	109.5
C9—C10—H10B	109.4	C17—O2—C18	119.1 (2)
H10A—C10—H10B	108.0
C6—C1—C2—C3	0.0 (4)	C6—C7—C8—C9	53.8 (2)
C1—C2—C3—C4	0.3 (4)	C15—C7—C8—C9	175.90 (17)
C2—C3—C4—C5	−0.5 (4)	C13—C8—C9—C10	55.4 (3)
C3—C4—C5—C6	0.4 (4)	C7—C8—C9—C10	−177.91 (19)
C2—C1—C6—C5	−0.1 (3)	C8—C9—C10—C11	−57.1 (3)
C2—C1—C6—C7	−179.3 (2)	C9—C10—C11—C12	56.5 (3)
C4—C5—C6—C1	−0.1 (3)	C10—C11—C12—C13	−56.4 (3)
C4—C5—C6—C7	179.1 (2)	C11—C12—C13—C8	56.4 (3)
C1—C6—C7—C14	1.1 (3)	C9—C8—C13—C12	−54.9 (3)
C5—C6—C7—C14	−178.02 (19)	C7—C8—C13—C12	179.0 (2)
C1—C6—C7—C15	118.6 (2)	C14—C7—C15—C16	62.0 (2)
C5—C6—C7—C15	−60.5 (2)	C6—C7—C15—C16	−57.2 (2)
C1—C6—C7—C8	−118.2 (2)	C8—C7—C15—C16	179.7 (2)
C5—C6—C7—C8	62.6 (2)	C7—C15—C16—C17	176.7 (2)
C14—C7—C8—C13	57.8 (2)	C15—C16—C17—O1	−7.4 (4)
C6—C7—C8—C13	178.43 (18)	C15—C16—C17—O2	170.7 (2)
C15—C7—C8—C13	−59.5 (3)	O1—C17—O2—C18	−1.8 (5)
C14—C7—C8—C9	−66.8 (2)	C16—C17—O2—C18	180.0 (2)