(4-Ethyl-cyclo-hex-yl)(4-meth-oxy-phen-yl)methanone.

In the title compound, C16H22O2, the cyclo-hexane ring adopts a chair conformation and its mean plane subtends a dihedral angle of 54.2 (6)° with the benzene ring. The crystal structure is stabilized by van der Waals inter-actions only with no classical inter-molecular hydrogen bonding observed.

Related literature

For details of SGLT2 inhibitors, a new class of hypoglycemic agents, see: Washburn (2009 ▶); Zhao et al. (2011 ▶); Shao et al. (2011 ▶). For the crystal structures of cyclo­hexyl derivertives, see: Wang et al. (2011 ▶).

Experimental

Crystal data

C16H22O2

M = 246.34

Monoclinic,

a = 7.613 (2) Å

b = 5.7513 (15) Å

c = 31.085 (9) Å

β = 94.674 (4)°

V = 1356.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009) ▶ T min = 0.985, T max = 0.992

13145 measured reflections

3235 independent reflections

2576 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.139

S = 1.06

3235 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009) ▶; cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003279/hg5288sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003279/hg5288Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003279/hg5288Isup3.cml

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

C16H22O2	F(000) = 536
Mr = 246.34	Dx = 1.206 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3595 reflections
a = 7.613 (2) Å	θ = 1.3–27.9°
b = 5.7513 (15) Å	µ = 0.08 mm−1
c = 31.085 (9) Å	T = 113 K
β = 94.674 (4)°	Prism, colorless
V = 1356.5 (6) Å3	0.20 × 0.18 × 0.10 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3235 independent reflections
Radiation source: rotating anode	2576 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.042
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.3°
ω and φ scans	h = −9→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)	k = −6→7
Tmin = 0.985, Tmax = 0.992	l = −40→40
13145 measured reflections

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) = 0.139	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0684P)2 + 0.0117P] where P = (Fo2 + 2Fc2)/3
3235 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
O1	0.34006 (12)	0.74119 (17)	0.16856 (3)	0.0272 (3)
O2	0.05937 (15)	0.53751 (18)	0.34949 (3)	0.0352 (3)
C1	0.3969 (2)	0.9518 (3)	0.14967 (4)	0.0316 (4)
H1A	0.3107	1.0750	0.1536	0.047*
H1B	0.4073	0.9276	0.1188	0.047*
H1C	0.5117	0.9974	0.1637	0.047*
C2	0.29562 (17)	0.7517 (2)	0.21018 (4)	0.0215 (3)
C3	0.20950 (17)	0.5560 (2)	0.22446 (4)	0.0229 (3)
H3	0.1869	0.4273	0.2057	0.028*
C4	0.15706 (17)	0.5488 (2)	0.26592 (4)	0.0212 (3)
H4	0.0986	0.4147	0.2755	0.025*
C5	0.18896 (17)	0.7370 (2)	0.29413 (4)	0.0198 (3)
C6	0.27745 (17)	0.9302 (2)	0.27951 (4)	0.0215 (3)
H6	0.3013	1.0582	0.2984	0.026*
C7	0.33165 (18)	0.9393 (2)	0.23779 (4)	0.0215 (3)
H7	0.3923	1.0718	0.2283	0.026*
C8	0.12147 (18)	0.7220 (2)	0.33787 (4)	0.0229 (3)
C9	0.13144 (17)	0.9305 (2)	0.36774 (4)	0.0213 (3)
H9	0.1151	1.0748	0.3499	0.026*
C10	−0.01352 (18)	0.9211 (2)	0.39925 (4)	0.0245 (3)
H10A	−0.1303	0.9292	0.3828	0.029*
H10B	−0.0061	0.7714	0.4150	0.029*
C11	0.00388 (17)	1.1215 (2)	0.43170 (4)	0.0239 (3)
H11A	−0.0890	1.1069	0.4521	0.029*
H11B	−0.0144	1.2708	0.4161	0.029*
C12	0.18477 (18)	1.1241 (2)	0.45716 (4)	0.0219 (3)
H12	0.2001	0.9730	0.4730	0.026*
C13	0.32707 (18)	1.1398 (2)	0.42528 (4)	0.0235 (3)
H13A	0.4446	1.1378	0.4414	0.028*
H13B	0.3147	1.2892	0.4095	0.028*
C14	0.31498 (18)	0.9391 (2)	0.39280 (4)	0.0233 (3)
H14A	0.3376	0.7903	0.4083	0.028*
H14B	0.4064	0.9588	0.3722	0.028*
C15	0.19885 (19)	1.3203 (3)	0.49047 (4)	0.0264 (3)
H15A	0.2086	1.4700	0.4751	0.032*
H15B	0.0886	1.3248	0.5053	0.032*
C16	0.3545 (2)	1.2989 (3)	0.52446 (4)	0.0319 (4)
H16A	0.3385	1.1616	0.5424	0.048*
H16B	0.3609	1.4383	0.5427	0.048*
H16C	0.4639	1.2832	0.5101	0.048*

	U11	U22	U33	U12	U13	U23
O1	0.0309 (6)	0.0321 (6)	0.0196 (5)	−0.0005 (4)	0.0068 (4)	−0.0025 (4)
O2	0.0550 (7)	0.0257 (6)	0.0261 (6)	−0.0095 (5)	0.0099 (5)	0.0028 (4)
C1	0.0357 (9)	0.0380 (10)	0.0223 (7)	0.0010 (7)	0.0089 (6)	0.0029 (6)
C2	0.0185 (7)	0.0272 (8)	0.0186 (6)	0.0026 (6)	0.0004 (5)	−0.0004 (5)
C3	0.0230 (7)	0.0221 (8)	0.0234 (7)	0.0009 (6)	0.0000 (5)	−0.0032 (5)
C4	0.0197 (7)	0.0188 (7)	0.0247 (7)	−0.0007 (5)	−0.0008 (5)	0.0022 (5)
C5	0.0200 (7)	0.0209 (7)	0.0180 (6)	0.0014 (5)	−0.0012 (5)	0.0012 (5)
C6	0.0231 (7)	0.0220 (8)	0.0188 (7)	0.0000 (6)	−0.0010 (5)	−0.0005 (5)
C7	0.0212 (7)	0.0216 (8)	0.0218 (7)	−0.0007 (5)	0.0018 (5)	0.0016 (5)
C8	0.0233 (7)	0.0232 (8)	0.0216 (7)	0.0001 (6)	−0.0008 (5)	0.0038 (5)
C9	0.0252 (8)	0.0221 (8)	0.0167 (6)	−0.0005 (6)	0.0022 (5)	0.0025 (5)
C10	0.0237 (8)	0.0296 (8)	0.0203 (7)	−0.0025 (6)	0.0021 (5)	0.0020 (5)
C11	0.0224 (7)	0.0300 (8)	0.0198 (6)	0.0019 (6)	0.0057 (5)	0.0019 (5)
C12	0.0251 (7)	0.0233 (8)	0.0177 (6)	0.0006 (6)	0.0034 (5)	0.0015 (5)
C13	0.0229 (7)	0.0257 (8)	0.0221 (7)	−0.0018 (6)	0.0026 (5)	0.0001 (5)
C14	0.0230 (7)	0.0267 (8)	0.0207 (7)	0.0005 (6)	0.0043 (5)	−0.0007 (5)
C15	0.0316 (8)	0.0260 (8)	0.0221 (7)	0.0012 (6)	0.0043 (6)	−0.0015 (5)
C16	0.0367 (9)	0.0360 (9)	0.0230 (7)	−0.0035 (7)	0.0025 (6)	−0.0045 (6)

O1—C2	1.3649 (15)	C10—C11	1.5302 (18)
O1—C1	1.4286 (16)	C10—H10A	0.9900
O2—C8	1.2281 (16)	C10—H10B	0.9900
C1—H1A	0.9800	C11—C12	1.5313 (18)
C1—H1B	0.9800	C11—H11A	0.9900
C1—H1C	0.9800	C11—H11B	0.9900
C2—C7	1.3923 (18)	C12—C13	1.5294 (18)
C2—C3	1.3933 (19)	C12—C15	1.5295 (18)
C3—C4	1.3805 (18)	C12—H12	1.0000
C3—H3	0.9500	C13—C14	1.5315 (18)
C4—C5	1.4017 (18)	C13—H13A	0.9900
C4—H4	0.9500	C13—H13B	0.9900
C5—C6	1.3941 (18)	C14—H14A	0.9900
C5—C8	1.4946 (18)	C14—H14B	0.9900
C6—C7	1.3935 (17)	C15—C16	1.5269 (19)
C6—H6	0.9500	C15—H15A	0.9900
C7—H7	0.9500	C15—H15B	0.9900
C8—C9	1.5146 (18)	C16—H16A	0.9800
C9—C10	1.5352 (18)	C16—H16B	0.9800
C9—C14	1.5441 (18)	C16—H16C	0.9800
C9—H9	1.0000
C2—O1—C1	117.31 (11)	C9—C10—H10B	109.3
O1—C1—H1A	109.5	H10A—C10—H10B	108.0
O1—C1—H1B	109.5	C10—C11—C12	111.94 (11)
H1A—C1—H1B	109.5	C10—C11—H11A	109.2
O1—C1—H1C	109.5	C12—C11—H11A	109.2
H1A—C1—H1C	109.5	C10—C11—H11B	109.2
H1B—C1—H1C	109.5	C12—C11—H11B	109.2
O1—C2—C7	124.55 (12)	H11A—C11—H11B	107.9
O1—C2—C3	115.20 (12)	C13—C12—C15	112.37 (11)
C7—C2—C3	120.25 (12)	C13—C12—C11	108.69 (11)
C4—C3—C2	120.06 (12)	C15—C12—C11	111.55 (11)
C4—C3—H3	120.0	C13—C12—H12	108.0
C2—C3—H3	120.0	C15—C12—H12	108.0
C3—C4—C5	120.83 (13)	C11—C12—H12	108.0
C3—C4—H4	119.6	C12—C13—C14	112.00 (11)
C5—C4—H4	119.6	C12—C13—H13A	109.2
C6—C5—C4	118.36 (12)	C14—C13—H13A	109.2
C6—C5—C8	123.61 (12)	C12—C13—H13B	109.2
C4—C5—C8	118.01 (12)	C14—C13—H13B	109.2
C7—C6—C5	121.40 (12)	H13A—C13—H13B	107.9
C7—C6—H6	119.3	C13—C14—C9	111.10 (11)
C5—C6—H6	119.3	C13—C14—H14A	109.4
C2—C7—C6	119.08 (12)	C9—C14—H14A	109.4
C2—C7—H7	120.5	C13—C14—H14B	109.4
C6—C7—H7	120.5	C9—C14—H14B	109.4
O2—C8—C5	119.12 (12)	H14A—C14—H14B	108.0
O2—C8—C9	120.34 (12)	C16—C15—C12	114.64 (12)
C5—C8—C9	120.54 (12)	C16—C15—H15A	108.6
C8—C9—C10	111.14 (11)	C12—C15—H15A	108.6
C8—C9—C14	109.43 (11)	C16—C15—H15B	108.6
C10—C9—C14	110.31 (11)	C12—C15—H15B	108.6
C8—C9—H9	108.6	H15A—C15—H15B	107.6
C10—C9—H9	108.6	C15—C16—H16A	109.5
C14—C9—H9	108.6	C15—C16—H16B	109.5
C11—C10—C9	111.47 (11)	H16A—C16—H16B	109.5
C11—C10—H10A	109.3	C15—C16—H16C	109.5
C9—C10—H10A	109.3	H16A—C16—H16C	109.5
C11—C10—H10B	109.3	H16B—C16—H16C	109.5
C1—O1—C2—C7	−12.28 (19)	O2—C8—C9—C10	−27.46 (17)
C1—O1—C2—C3	168.14 (11)	C5—C8—C9—C10	153.29 (12)
O1—C2—C3—C4	−179.40 (11)	O2—C8—C9—C14	94.61 (15)
C7—C2—C3—C4	1.0 (2)	C5—C8—C9—C14	−84.64 (14)
C2—C3—C4—C5	0.1 (2)	C8—C9—C10—C11	175.81 (10)
C3—C4—C5—C6	−1.00 (19)	C14—C9—C10—C11	54.25 (14)
C3—C4—C5—C8	177.29 (12)	C9—C10—C11—C12	−56.99 (14)
C4—C5—C6—C7	0.78 (19)	C10—C11—C12—C13	57.33 (14)
C8—C5—C6—C7	−177.40 (12)	C10—C11—C12—C15	−178.23 (11)
O1—C2—C7—C6	179.23 (12)	C15—C12—C13—C14	178.48 (10)
C3—C2—C7—C6	−1.21 (19)	C11—C12—C13—C14	−57.57 (14)
C5—C6—C7—C2	0.3 (2)	C12—C13—C14—C9	57.13 (15)
C6—C5—C8—O2	−173.42 (12)	C8—C9—C14—C13	−176.81 (11)
C4—C5—C8—O2	8.38 (19)	C10—C9—C14—C13	−54.24 (14)
C6—C5—C8—C9	5.83 (19)	C13—C12—C15—C16	−72.27 (15)
C4—C5—C8—C9	−172.36 (12)	C11—C12—C15—C16	165.39 (12)