Cyclo­hexyl phenyl ketone

The C=O bond of the title compound, C₁₃H₁₇O, is essentially coplanar with the phenyl ring. The cyclo­hexyl ring is in the chair conformation and its least-squares plane is at an angle of 55.48 (9)° to the phenyl ring. No intermolecular hydrogen bonding is exhibited.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.080
• Data-to-parameter ratio = 9.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack    4.000
         From the CIF: _refine_ls_abs_structure_Flack_su    2.000
           Alert C Chirality of atom sites is inverted?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.00
         From the CIF: _reflns_number_total               1220
         Count of symmetry unique reflns         1220
         Completeness (_total/calc)            100.00%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON.

Cyclohexyl phenyl ketone

Crystal data

C13H16O	Dx = 1.181 Mg m^−3
Mr = 188.26	Melting point = 329–330 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 9.3624 (6) Å	Cell parameters from 4618 reflections
b = 9.8350 (6) Å	θ = 2.7–24.5°
c = 11.5019 (7) Å	µ = 0.07 mm^−1
V = 1059.09 (11) Å^3	T = 120 K
Z = 4	Irregular fragment, colorless
F(000) = 408	0.20 × 0.18 × 0.14 mm

Data collection

Bruker CCD area-detector diffractometer	1023 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.056
Graphite monochromator	θmax = 26.0°, θmin = 2.7°
φ and ω scans	h = −11→11
16430 measured reflections	k = −12→12
1220 independent reflections	l = −14→14

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.0878P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.080	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.14 e Å^−3
1220 reflections	Δρmin = −0.12 e Å^−3
128 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.015 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration could not be determined because of the lack of significant anomalous scattering effects.
Secondary atom site location: difference Fourier map	Absolute structure parameter: 4 (2)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.72456 (14)	0.11226 (13)	0.58334 (12)	0.0367 (4)
C1	0.87357 (19)	0.22926 (17)	0.71463 (15)	0.0244 (4)
C2	0.8259 (2)	0.14977 (19)	0.80750 (16)	0.0315 (5)
C3	0.8796 (2)	0.16917 (19)	0.91852 (16)	0.0350 (4)
C4	0.9810 (2)	0.2692 (2)	0.93825 (16)	0.0363 (5)
C5	1.0275 (2)	0.3504 (2)	0.84726 (16)	0.0338 (5)
C6	0.97448 (19)	0.33100 (18)	0.73603 (15)	0.0283 (4)
C7	0.81768 (18)	0.19894 (17)	0.59494 (16)	0.0265 (4)
C8	0.87579 (19)	0.27392 (17)	0.48995 (15)	0.0250 (4)
C9	0.7979 (2)	0.41066 (18)	0.47524 (16)	0.0310 (5)
C10	0.8519 (2)	0.48573 (19)	0.36769 (17)	0.0358 (5)
C11	0.8346 (2)	0.3993 (2)	0.25875 (17)	0.0395 (5)
C12	0.9095 (2)	0.2624 (2)	0.27166 (16)	0.0388 (5)
C13	0.8599 (2)	0.18749 (19)	0.37983 (15)	0.0319 (4)
H2	0.7573	0.0831	0.7947	0.038*
H3	0.8478	0.1152	0.9796	0.042*
H4	1.0179	0.2819	1.0125	0.044*
H5	1.0946	0.4182	0.8610	0.041*
H6	1.0061	0.3858	0.6754	0.034*
H8	0.9775	0.2920	0.5027	0.030*
H9A	0.6961	0.3947	0.4679	0.037*
H9B	0.8136	0.4664	0.5436	0.037*
H10A	0.7990	0.5699	0.3585	0.043*
H10B	0.9519	0.5085	0.3780	0.043*
H11A	0.8743	0.4475	0.1926	0.047*
H11B	0.7338	0.3844	0.2440	0.047*
H12A	0.8901	0.2071	0.2037	0.047*
H12B	1.0119	0.2768	0.2760	0.047*
H13A	0.9152	0.1047	0.3885	0.038*
H13B	0.7605	0.1620	0.3705	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0354 (7)	0.0362 (7)	0.0386 (8)	−0.0111 (6)	−0.0034 (6)	0.0019 (7)
C1	0.0249 (9)	0.0208 (8)	0.0275 (9)	0.0036 (7)	0.0023 (8)	0.0017 (7)
C2	0.0330 (10)	0.0267 (9)	0.0346 (10)	0.0010 (8)	0.0040 (8)	0.0025 (8)
C3	0.0438 (11)	0.0331 (9)	0.0282 (9)	0.0011 (9)	0.0036 (9)	0.0095 (9)
C4	0.0434 (11)	0.0397 (11)	0.0259 (9)	0.0000 (9)	−0.0041 (9)	0.0005 (9)
C5	0.0379 (10)	0.0324 (10)	0.0312 (9)	−0.0047 (9)	−0.0015 (9)	−0.0006 (9)
C6	0.0311 (10)	0.0271 (9)	0.0268 (9)	−0.0029 (8)	0.0027 (8)	0.0031 (8)
C7	0.0239 (9)	0.0230 (8)	0.0324 (10)	0.0023 (7)	−0.0011 (8)	−0.0002 (8)
C8	0.0230 (9)	0.0266 (9)	0.0254 (9)	0.0002 (8)	−0.0007 (7)	−0.0012 (8)
C9	0.0349 (10)	0.0276 (9)	0.0304 (10)	0.0030 (9)	−0.0007 (9)	−0.0006 (8)
C10	0.0381 (11)	0.0315 (9)	0.0378 (11)	0.0001 (9)	−0.0041 (10)	0.0081 (9)
C11	0.0415 (11)	0.0479 (11)	0.0291 (10)	−0.0062 (10)	−0.0054 (9)	0.0098 (10)
C12	0.0416 (11)	0.0474 (12)	0.0274 (11)	0.0004 (10)	0.0001 (9)	−0.0085 (10)
C13	0.0336 (10)	0.0326 (10)	0.0297 (10)	0.0010 (9)	−0.0028 (9)	−0.0039 (8)

Geometric parameters (Å, º)

O1—C7	1.227 (2)	C3—H3	0.9300
C1—C2	1.397 (2)	C4—H4	0.9300
C1—C6	1.398 (2)	C5—H5	0.9300
C1—C7	1.503 (2)	C6—H6	0.9300
C2—C3	1.386 (3)	C8—H8	0.9800
C3—C4	1.386 (3)	C9—H9A	0.9700
C4—C5	1.386 (3)	C9—H9B	0.9700
C5—C6	1.385 (2)	C10—H10A	0.9700
C7—C8	1.516 (2)	C10—H10B	0.9700
C8—C13	1.533 (2)	C11—H11A	0.9700
C8—C9	1.539 (2)	C11—H11B	0.9700
C9—C10	1.527 (3)	C12—H12A	0.9700
C10—C11	1.523 (3)	C12—H12B	0.9700
C11—C12	1.525 (3)	C13—H13A	0.9700
C12—C13	1.519 (3)	C13—H13B	0.9700
C2—H2	0.9300
C2—C1—C6	118.81 (16)	C7—C8—H8	108.6
C2—C1—C7	118.57 (15)	C13—C8—H8	108.6
C6—C1—C7	122.59 (15)	C9—C8—H8	108.6
C3—C2—C1	120.77 (18)	C10—C9—H9A	109.5
C4—C3—C2	119.83 (18)	C8—C9—H9A	109.5
C3—C4—C5	120.02 (18)	C10—C9—H9B	109.5
C6—C5—C4	120.35 (18)	C8—C9—H9B	109.5
C5—C6—C1	120.21 (17)	H9A—C9—H9B	108.1
O1—C7—C1	119.02 (16)	C11—C10—H10A	109.4
O1—C7—C8	120.43 (16)	C9—C10—H10A	109.4
C1—C7—C8	120.55 (14)	C11—C10—H10B	109.4
C7—C8—C13	110.71 (13)	C9—C10—H10B	109.4
C7—C8—C9	110.04 (14)	H10A—C10—H10B	108.0
C13—C8—C9	110.35 (14)	C10—C11—H11A	109.4
C10—C9—C8	110.79 (15)	C12—C11—H11A	109.4
C11—C10—C9	111.19 (15)	C10—C11—H11B	109.4
C10—C11—C12	111.33 (16)	C12—C11—H11B	109.4
C13—C12—C11	111.56 (17)	H11A—C11—H11B	108.0
C12—C13—C8	112.21 (15)	C13—C12—H12A	109.3
C3—C2—H2	119.6	C11—C12—H12A	109.3
C1—C2—H2	119.6	C13—C12—H12B	109.3
C4—C3—H3	120.1	C11—C12—H12B	109.3
C2—C3—H3	120.1	H12A—C12—H12B	108.0
C3—C4—H4	120.0	C12—C13—H13A	109.2
C5—C4—H4	120.0	C8—C13—H13A	109.2
C6—C5—H5	119.8	C12—C13—H13B	109.2
C4—C5—H5	119.8	C8—C13—H13B	109.2
C5—C6—H6	119.9	H13A—C13—H13B	107.9
C1—C6—H6	119.9
C6—C1—C2—C3	−1.4 (3)	O1—C7—C8—C13	−26.2 (2)
C7—C1—C2—C3	176.72 (17)	C1—C7—C8—C13	153.56 (15)
C1—C2—C3—C4	0.5 (3)	O1—C7—C8—C9	96.04 (19)
C2—C3—C4—C5	0.6 (3)	C1—C7—C8—C9	−84.19 (19)
C3—C4—C5—C6	−0.8 (3)	C7—C8—C9—C10	−178.27 (15)
C4—C5—C6—C1	0.0 (3)	C13—C8—C9—C10	−55.81 (19)
C2—C1—C6—C5	1.1 (3)	C8—C9—C10—C11	57.0 (2)
C7—C1—C6—C5	−176.90 (18)	C9—C10—C11—C12	−56.1 (2)
C2—C1—C7—O1	5.2 (2)	C10—C11—C12—C13	54.4 (2)
C6—C1—C7—O1	−176.81 (16)	C11—C12—C13—C8	−54.2 (2)
C2—C1—C7—C8	−174.59 (16)	C7—C8—C13—C12	176.84 (16)
C6—C1—C7—C8	3.4 (2)	C9—C8—C13—C12	54.8 (2)