2-[2-(Cyclo­hexyl­carbon­yl)phen­yl]-1-phenyl­ethanone

Khan, F.N.; Manivel, P.; Prabakaran, K.; Hathwar, V.R.; Ng, S.W.

doi:10.1107/S1600536809041270

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2745

https://doi.org/10.1107/S1600536809041270

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2-[2-(Cyclohexylcarbonyl)phenyl]-1-phenylethanone

F. Nawaz Khan,^a P. Manivel,^a K. Prabakaran,^a Venkatesha R. Hathwar ^b and Seik Weng Ng ^c ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 October 2009; accepted 9 October 2009; online 17 October 2009)

The title diketone, C₂₁H₂₂O₂, features a phenylene ring having benzoylmethyl and cyclohexanoyl substituents ortho to each other. The cyclohexyl ring adopts a chair conformation with the ketonic group occupying an equatorial position; the four-atom –C(O)–C ketonic unit is twisted out of the plane of the phenylene ring by 34.9 (1)°.

Related literature

For the synthesis of this and other 1,2-phenylethanones from isocoumarins, see: Manivel et al. (2008 ).

Experimental

Crystal data

C₂₁H₂₂O₂
M_r = 306.39
Monoclinic, P 2₁ /c
a = 10.4012 (6) Å
b = 10.1132 (6) Å
c = 16.0981 (9) Å
β = 90.038 (1)°
V = 1693.35 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 K
0.25 × 0.22 × 0.18 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: none
11930 measured reflections
2984 independent reflections
2797 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.183
S = 1.32
2984 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809041270/tk2553sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041270/tk2553Isup2.hkl

checkCIF report

Related literature top

For the synthesis of this and other 1,2-phenylethanones from isocoumarins, see: Manivel et al. (2008).

Experimental top

The compound was synthesized as described by Manivel et al. (2008). Single crystals were grown from its solution in ether.

Structure description top

For the synthesis of this and other 1,2-phenylethanones from isocoumarins, see: Manivel et al. (2008).

Computing details top

Data collection: SMART (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₁H₂₂O₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

2-[2-(Cyclohexylcarbonyl)phenyl]-1-phenylethanone top

Crystal data top

C₂₁H₂₂O₂	F(000) = 656
M_r = 306.39	D_x = 1.202 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 878 reflections
a = 10.4012 (6) Å	θ = 2.4–25.3°
b = 10.1132 (6) Å	µ = 0.08 mm⁻¹
c = 16.0981 (9) Å	T = 290 K
β = 90.038 (1)°	Block, colorless
V = 1693.35 (17) Å³	0.25 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker SMART area-detector diffractometer	2797 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
φ and ω scans	h = −12→12
11930 measured reflections	k = −12→12
2984 independent reflections	l = −18→19

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.32	w = 1/[σ²(F_o²) + (0.068P)² + 0.5871P] where P = (F_o² + 2F_c²)/3
2984 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₂₂O₂	V = 1693.35 (17) Å³
M_r = 306.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4012 (6) Å	µ = 0.08 mm⁻¹
b = 10.1132 (6) Å	T = 290 K
c = 16.0981 (9) Å	0.25 × 0.22 × 0.18 mm
β = 90.038 (1)°

Data collection top

Bruker SMART area-detector diffractometer	2797 reflections with I > 2σ(I)
11930 measured reflections	R_int = 0.025
2984 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.32	Δρ_max = 0.18 e Å⁻³
2984 reflections	Δρ_min = −0.18 e Å⁻³
208 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.63291 (18)	0.81169 (19)	0.64919 (12)	0.0603 (6)
O2	0.83697 (18)	0.5709 (2)	0.67129 (13)	0.0649 (6)
C1	0.8136 (2)	0.9209 (2)	0.70629 (15)	0.0444 (6)
H1	0.8661	0.9089	0.7563	0.053*
C2	0.8988 (3)	0.8982 (3)	0.63032 (19)	0.0617 (8)
H2A	0.9350	0.8099	0.6326	0.074*
H2B	0.8472	0.9047	0.5803	0.074*
C3	1.0069 (3)	0.9992 (4)	0.6269 (2)	0.0772 (10)
H3A	1.0633	0.9868	0.6743	0.093*
H3B	1.0570	0.9855	0.5769	0.093*
C4	0.9553 (4)	1.1381 (4)	0.6276 (2)	0.0855 (11)
H4A	0.9063	1.1536	0.5772	0.103*
H4B	1.0264	1.2001	0.6285	0.103*
C5	0.8704 (3)	1.1617 (3)	0.7022 (2)	0.0737 (9)
H5A	0.8346	1.2501	0.6993	0.088*
H5B	0.9216	1.1555	0.7524	0.088*
C6	0.7621 (3)	1.0616 (3)	0.7059 (2)	0.0593 (7)
H6A	0.7062	1.0736	0.6582	0.071*
H6B	0.7116	1.0764	0.7556	0.071*
C7	0.7044 (2)	0.8228 (2)	0.70871 (15)	0.0426 (6)
C8	0.6826 (2)	0.7417 (2)	0.78542 (14)	0.0405 (6)
C9	0.7074 (2)	0.7974 (3)	0.86283 (15)	0.0468 (6)
H9	0.7392	0.8832	0.8655	0.056*
C10	0.6862 (3)	0.7290 (3)	0.93556 (16)	0.0543 (7)
H10	0.7033	0.7683	0.9866	0.065*
C11	0.6397 (3)	0.6023 (3)	0.93171 (17)	0.0574 (7)
H11	0.6245	0.5551	0.9803	0.069*
C12	0.6154 (2)	0.5451 (3)	0.85552 (18)	0.0520 (7)
H12	0.5841	0.4590	0.8538	0.062*
C13	0.6361 (2)	0.6117 (2)	0.78134 (15)	0.0432 (6)
C14	0.6148 (2)	0.5387 (3)	0.70076 (17)	0.0499 (7)
H14A	0.5514	0.5862	0.6681	0.060*
H14B	0.5800	0.4519	0.7130	0.060*
C15	0.7363 (2)	0.5223 (2)	0.64918 (16)	0.0440 (6)
C16	0.7295 (2)	0.4449 (2)	0.57069 (15)	0.0421 (6)
C17	0.6237 (3)	0.3730 (3)	0.54615 (18)	0.0631 (8)
H17	0.5501	0.3733	0.5788	0.076*
C18	0.6259 (3)	0.3006 (3)	0.4736 (2)	0.0720 (9)
H18	0.5537	0.2525	0.4578	0.086*
C19	0.7325 (3)	0.2990 (3)	0.42538 (18)	0.0636 (8)
H19	0.7339	0.2490	0.3769	0.076*
C20	0.8376 (3)	0.3707 (3)	0.4480 (2)	0.0706 (9)
H20	0.9102	0.3711	0.4144	0.085*
C21	0.8365 (3)	0.4425 (3)	0.52045 (19)	0.0633 (8)
H21	0.9091	0.4903	0.5358	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0612 (12)	0.0688 (13)	0.0509 (11)	−0.0129 (10)	−0.0135 (10)	0.0076 (9)
O2	0.0428 (10)	0.0826 (15)	0.0694 (13)	−0.0102 (10)	0.0025 (9)	−0.0298 (11)
C1	0.0458 (14)	0.0501 (15)	0.0374 (13)	−0.0036 (11)	−0.0054 (10)	0.0045 (11)
C2	0.0532 (16)	0.072 (2)	0.0597 (18)	−0.0021 (14)	0.0077 (13)	−0.0045 (15)
C3	0.0565 (18)	0.108 (3)	0.067 (2)	−0.0182 (19)	0.0109 (15)	0.0035 (19)
C4	0.087 (2)	0.095 (3)	0.075 (2)	−0.043 (2)	−0.0039 (19)	0.022 (2)
C5	0.087 (2)	0.0552 (18)	0.079 (2)	−0.0176 (16)	−0.0054 (18)	0.0040 (16)
C6	0.0614 (17)	0.0513 (17)	0.0653 (18)	−0.0026 (13)	0.0027 (14)	0.0011 (14)
C7	0.0435 (13)	0.0449 (14)	0.0394 (13)	0.0032 (11)	−0.0036 (11)	−0.0012 (11)
C8	0.0337 (12)	0.0465 (14)	0.0412 (13)	0.0018 (10)	0.0023 (10)	−0.0029 (11)
C9	0.0506 (14)	0.0468 (14)	0.0431 (14)	0.0009 (11)	0.0014 (11)	−0.0050 (11)
C10	0.0537 (16)	0.0687 (19)	0.0407 (14)	0.0036 (14)	0.0055 (12)	−0.0033 (13)
C11	0.0555 (16)	0.0702 (19)	0.0466 (16)	0.0046 (14)	0.0087 (13)	0.0116 (14)
C12	0.0455 (15)	0.0500 (15)	0.0606 (17)	−0.0017 (12)	0.0069 (12)	0.0055 (13)
C13	0.0342 (12)	0.0483 (14)	0.0472 (14)	0.0014 (10)	0.0060 (10)	−0.0024 (11)
C14	0.0442 (14)	0.0488 (15)	0.0567 (16)	−0.0082 (11)	0.0024 (12)	−0.0057 (12)
C15	0.0400 (13)	0.0416 (13)	0.0503 (15)	−0.0039 (11)	−0.0025 (11)	−0.0032 (11)
C16	0.0452 (13)	0.0355 (13)	0.0457 (14)	−0.0013 (10)	−0.0016 (11)	−0.0003 (10)
C17	0.0546 (17)	0.076 (2)	0.0592 (18)	−0.0195 (15)	0.0067 (13)	−0.0189 (15)
C18	0.070 (2)	0.080 (2)	0.065 (2)	−0.0255 (17)	−0.0016 (16)	−0.0239 (17)
C19	0.087 (2)	0.0557 (17)	0.0480 (16)	−0.0083 (16)	0.0014 (15)	−0.0103 (13)
C20	0.070 (2)	0.079 (2)	0.0626 (19)	−0.0104 (17)	0.0167 (16)	−0.0213 (17)
C21	0.0504 (16)	0.0703 (19)	0.0693 (19)	−0.0135 (14)	0.0090 (14)	−0.0198 (16)

Geometric parameters (Å, º) top

O1—C7	1.218 (3)	C9—H9	0.9300
O2—C15	1.210 (3)	C10—C11	1.371 (4)
C1—C7	1.509 (3)	C10—H10	0.9300
C1—C6	1.520 (4)	C11—C12	1.380 (4)
C1—C2	1.528 (4)	C11—H11	0.9300
C1—H1	0.9800	C12—C13	1.388 (4)
C2—C3	1.520 (4)	C12—H12	0.9300
C2—H2A	0.9700	C13—C14	1.509 (4)
C2—H2B	0.9700	C14—C15	1.521 (4)
C3—C4	1.504 (5)	C14—H14A	0.9700
C3—H3A	0.9700	C14—H14B	0.9700
C3—H3B	0.9700	C15—C16	1.488 (3)
C4—C5	1.510 (5)	C16—C21	1.376 (4)
C4—H4A	0.9700	C16—C17	1.376 (4)
C4—H4B	0.9700	C17—C18	1.378 (4)
C5—C6	1.515 (4)	C17—H17	0.9300
C5—H5A	0.9700	C18—C19	1.355 (4)
C5—H5B	0.9700	C18—H18	0.9300
C6—H6A	0.9700	C19—C20	1.361 (4)
C6—H6B	0.9700	C19—H19	0.9300
C7—C8	1.500 (3)	C20—C21	1.374 (4)
C8—C9	1.392 (3)	C20—H20	0.9300
C8—C13	1.402 (4)	C21—H21	0.9300
C9—C10	1.378 (4)

C7—C1—C6	110.5 (2)	C10—C9—C8	121.9 (2)
C7—C1—C2	111.0 (2)	C10—C9—H9	119.1
C6—C1—C2	110.0 (2)	C8—C9—H9	119.1
C7—C1—H1	108.4	C11—C10—C9	119.2 (3)
C6—C1—H1	108.4	C11—C10—H10	120.4
C2—C1—H1	108.4	C9—C10—H10	120.4
C3—C2—C1	110.9 (2)	C10—C11—C12	119.8 (3)
C3—C2—H2A	109.5	C10—C11—H11	120.1
C1—C2—H2A	109.5	C12—C11—H11	120.1
C3—C2—H2B	109.5	C11—C12—C13	122.2 (3)
C1—C2—H2B	109.5	C11—C12—H12	118.9
H2A—C2—H2B	108.1	C13—C12—H12	118.9
C4—C3—C2	111.4 (3)	C12—C13—C8	118.0 (2)
C4—C3—H3A	109.4	C12—C13—C14	118.6 (2)
C2—C3—H3A	109.4	C8—C13—C14	123.3 (2)
C4—C3—H3B	109.4	C13—C14—C15	113.7 (2)
C2—C3—H3B	109.4	C13—C14—H14A	108.8
H3A—C3—H3B	108.0	C15—C14—H14A	108.8
C3—C4—C5	111.2 (3)	C13—C14—H14B	108.8
C3—C4—H4A	109.4	C15—C14—H14B	108.8
C5—C4—H4A	109.4	H14A—C14—H14B	107.7
C3—C4—H4B	109.4	O2—C15—C16	120.3 (2)
C5—C4—H4B	109.4	O2—C15—C14	120.9 (2)
H4A—C4—H4B	108.0	C16—C15—C14	118.8 (2)
C4—C5—C6	111.1 (3)	C21—C16—C17	117.9 (2)
C4—C5—H5A	109.4	C21—C16—C15	118.0 (2)
C6—C5—H5A	109.4	C17—C16—C15	124.0 (2)
C4—C5—H5B	109.4	C18—C17—C16	120.7 (3)
C6—C5—H5B	109.4	C18—C17—H17	119.6
H5A—C5—H5B	108.0	C16—C17—H17	119.6
C5—C6—C1	111.3 (2)	C19—C18—C17	120.4 (3)
C5—C6—H6A	109.4	C19—C18—H18	119.8
C1—C6—H6A	109.4	C17—C18—H18	119.8
C5—C6—H6B	109.4	C18—C19—C20	119.8 (3)
C1—C6—H6B	109.4	C18—C19—H19	120.1
H6A—C6—H6B	108.0	C20—C19—H19	120.1
O1—C7—C8	120.3 (2)	C19—C20—C21	120.1 (3)
O1—C7—C1	120.0 (2)	C19—C20—H20	119.9
C8—C7—C1	119.7 (2)	C21—C20—H20	119.9
C9—C8—C13	119.0 (2)	C20—C21—C16	121.0 (3)
C9—C8—C7	119.2 (2)	C20—C21—H21	119.5
C13—C8—C7	121.8 (2)	C16—C21—H21	119.5

C7—C1—C2—C3	178.6 (2)	C11—C12—C13—C14	176.2 (2)
C6—C1—C2—C3	56.0 (3)	C9—C8—C13—C12	0.9 (3)
C1—C2—C3—C4	−56.3 (4)	C7—C8—C13—C12	−178.3 (2)
C2—C3—C4—C5	55.9 (4)	C9—C8—C13—C14	−175.6 (2)
C3—C4—C5—C6	−55.8 (4)	C7—C8—C13—C14	5.3 (3)
C4—C5—C6—C1	56.4 (4)	C12—C13—C14—C15	−116.1 (3)
C7—C1—C6—C5	−179.2 (2)	C8—C13—C14—C15	60.3 (3)
C2—C1—C6—C5	−56.3 (3)	C13—C14—C15—O2	−3.5 (4)
C6—C1—C7—O1	67.7 (3)	C13—C14—C15—C16	176.3 (2)
C2—C1—C7—O1	−54.6 (3)	O2—C15—C16—C21	−6.8 (4)
C6—C1—C7—C8	−110.8 (3)	C14—C15—C16—C21	173.3 (3)
C2—C1—C7—C8	126.9 (2)	O2—C15—C16—C17	171.7 (3)
O1—C7—C8—C9	−143.9 (2)	C14—C15—C16—C17	−8.2 (4)
C1—C7—C8—C9	34.6 (3)	C21—C16—C17—C18	0.3 (5)
O1—C7—C8—C13	35.2 (3)	C15—C16—C17—C18	−178.2 (3)
C1—C7—C8—C13	−146.2 (2)	C16—C17—C18—C19	0.1 (5)
C13—C8—C9—C10	−0.8 (4)	C17—C18—C19—C20	−0.9 (5)
C7—C8—C9—C10	178.4 (2)	C18—C19—C20—C21	1.3 (5)
C8—C9—C10—C11	0.2 (4)	C19—C20—C21—C16	−0.9 (5)
C9—C10—C11—C12	0.3 (4)	C17—C16—C21—C20	0.1 (5)
C10—C11—C12—C13	−0.2 (4)	C15—C16—C21—C20	178.6 (3)
C11—C12—C13—C8	−0.4 (4)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂O₂
M_r	306.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	10.4012 (6), 10.1132 (6), 16.0981 (9)
β (°)	90.038 (1)
V (Å³)	1693.35 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11930, 2984, 2797
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.183, 1.32
No. of reflections	2984
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA-DST program. FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

References

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Manivel, P., Roopan, S. M. & Khan, F. N. (2008). Indian J. Heterocycl. Chem. 18, 21–24. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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