4-Ethoxycarbonyl-3-hydroxy-3-phenylcyclohexanone

The title compound, ethyl 2-hydroxy-4-oxo-2-phenyl­cyclo­hexane­carboxyl­ate, C₁₅H₁₈O₄, was obtained by a Michael–Aldol condensation and has the cyclo­hexanone in a chair conformation. The attached hydroxy, ethoxy­carbonyl and phenyl groups are disposed in β-axial, β-equatorial and α-­equatorial configurations, respectively. An intermolecular hydrogen bond, with an O...O distance of 2.874 (2) Å, links the OH group and the ring carbonyl. Weak intermolecular C—H...O=C (ester and ketone), O—H...O=C (ketone) and C—H...OH hydrogen bonds exist.

Computing details

Data collection: XSCANS (Siemens 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick 1990); software used to prepare material for publication: SHELXL97.

4-ethoxycarbonyl-3-hydroxy-3-phenylcyclohexanone

Crystal data

C15H18O4	F(000) = 560
Mr = 262.29	Dx = 1.274 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.601 (2) Å	Cell parameters from 40 reflections
b = 8.673 (2) Å	θ = 5.4–24.6°
c = 15.322 (5) Å	µ = 0.09 mm^−1
β = 103.81 (2)°	T = 293 K
V = 1368.0 (6) Å^3	Prism, colourless
Z = 4	0.38 × 0.24 × 0.10 mm

Data collection

Siemens P4/PC diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.0°
Graphite monochromator	h = 0→14
ω/2θ scans	k = 0→12
4191 measured reflections	l = −21→20
3996 independent reflections	3 standard reflections every 97 reflections
1517 reflections with I > 2σ(I)	intensity decay: <2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0481P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.77	(Δ/σ)max = 0.007
3996 reflections	Δρmax = 0.18 e Å^−3
176 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (11)

Special details

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.

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

	x	y	z	Uiso*/Ueq
O1	0.30074 (16)	0.3869 (2)	0.47348 (11)	0.0611 (5)
O2	0.58623 (16)	0.45965 (18)	0.65574 (11)	0.0428 (4)
H2	0.623 (2)	0.498 (3)	0.6197 (17)	0.051*
O3	0.56227 (17)	0.3697 (2)	0.85586 (10)	0.0569 (5)
O4	0.70470 (15)	0.1934 (2)	0.83221 (10)	0.0478 (4)
C1	0.3586 (2)	0.3069 (3)	0.53574 (14)	0.0419 (5)
C2	0.4977 (2)	0.2613 (3)	0.54688 (13)	0.0428 (5)
H2A	0.5327	0.3155	0.5025	0.051*
H2B	0.5019	0.1517	0.5353	0.051*
C3	0.5834 (2)	0.2969 (2)	0.64169 (13)	0.0340 (5)
C4	0.51743 (19)	0.2304 (2)	0.71452 (13)	0.0346 (5)
H4	0.5175	0.1177	0.7099	0.042*
C5	0.3763 (2)	0.2837 (3)	0.70039 (14)	0.0432 (5)
H5A	0.3378	0.2345	0.7446	0.052*
H5B	0.3745	0.3943	0.7095	0.052*
C6	0.2959 (2)	0.2444 (3)	0.60615 (16)	0.0495 (6)
H6A	0.2874	0.1334	0.5997	0.059*
H6B	0.2096	0.2878	0.5979	0.059*
C7	0.7190 (2)	0.2287 (3)	0.64830 (13)	0.0360 (5)
C8	0.7328 (2)	0.0708 (3)	0.63348 (16)	0.0468 (6)
H8	0.6600	0.0073	0.6208	0.056*
C9	0.8546 (3)	0.0091 (4)	0.6377 (2)	0.0620 (7)
H9	0.8628	−0.0959	0.6279	0.074*
C10	0.9641 (3)	0.1015 (4)	0.6565 (2)	0.0676 (8)
H10	1.0456	0.0594	0.6590	0.081*
C11	0.9508 (2)	0.2566 (4)	0.67138 (18)	0.0601 (7)
H11	1.0241	0.3193	0.6846	0.072*
C12	0.8295 (2)	0.3202 (3)	0.66695 (14)	0.0453 (6)
H12	0.8222	0.4253	0.6766	0.054*
C13	0.5944 (2)	0.2742 (3)	0.80848 (14)	0.0390 (5)
C14	0.7948 (2)	0.2368 (4)	0.91523 (16)	0.0624 (8)
H14A	0.7622	0.2040	0.9662	0.075*
H14B	0.8050	0.3479	0.9179	0.075*
C15	0.9206 (3)	0.1632 (4)	0.9180 (2)	0.0801 (10)
H15A	0.9133	0.0542	0.9265	0.096*
H15B	0.9854	0.2053	0.9669	0.096*
H15C	0.9450	0.1818	0.8625	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0484 (10)	0.0750 (13)	0.0580 (10)	0.0064 (10)	0.0089 (8)	0.0261 (10)
O2	0.0555 (10)	0.0311 (8)	0.0464 (9)	0.0003 (7)	0.0212 (7)	0.0065 (7)
O3	0.0754 (12)	0.0577 (12)	0.0380 (9)	0.0199 (10)	0.0141 (8)	−0.0055 (8)
O4	0.0476 (9)	0.0545 (11)	0.0386 (8)	0.0086 (8)	0.0051 (7)	−0.0046 (8)
C1	0.0414 (12)	0.0428 (13)	0.0395 (11)	0.0000 (11)	0.0056 (9)	0.0033 (10)
C2	0.0441 (12)	0.0525 (15)	0.0317 (10)	0.0051 (11)	0.0087 (9)	0.0003 (10)
C3	0.0394 (11)	0.0326 (11)	0.0303 (9)	0.0008 (9)	0.0091 (8)	0.0018 (9)
C4	0.0406 (11)	0.0290 (11)	0.0358 (10)	0.0029 (9)	0.0123 (8)	0.0043 (9)
C5	0.0446 (12)	0.0424 (13)	0.0470 (12)	0.0036 (11)	0.0195 (10)	0.0105 (11)
C6	0.0374 (11)	0.0510 (15)	0.0599 (14)	−0.0016 (11)	0.0112 (10)	0.0162 (12)
C7	0.0399 (11)	0.0393 (12)	0.0294 (9)	0.0024 (10)	0.0095 (8)	0.0021 (9)
C8	0.0467 (14)	0.0420 (14)	0.0524 (14)	0.0045 (11)	0.0133 (11)	−0.0021 (11)
C9	0.0625 (17)	0.0563 (17)	0.0704 (17)	0.0203 (14)	0.0225 (14)	0.0066 (14)
C10	0.0468 (16)	0.089 (2)	0.0720 (18)	0.0200 (16)	0.0236 (13)	0.0129 (17)
C11	0.0386 (13)	0.081 (2)	0.0603 (16)	−0.0006 (14)	0.0108 (11)	0.0135 (15)
C12	0.0437 (13)	0.0490 (14)	0.0430 (12)	−0.0029 (11)	0.0095 (10)	0.0018 (11)
C13	0.0512 (13)	0.0351 (12)	0.0347 (10)	0.0014 (11)	0.0178 (9)	0.0057 (9)
C14	0.0608 (15)	0.079 (2)	0.0417 (12)	0.0063 (15)	0.0010 (11)	−0.0101 (13)
C15	0.0594 (18)	0.104 (3)	0.0673 (19)	0.0023 (19)	−0.0042 (14)	−0.0031 (18)

Geometric parameters (Å, º)

O1—C1	1.220 (3)	C6—H6A	0.9700
O2—C3	1.427 (3)	C6—H6B	0.9700
O2—H2	0.82 (3)	C7—C12	1.386 (3)
O3—C13	1.203 (3)	C7—C8	1.401 (3)
O4—C13	1.337 (3)	C8—C9	1.385 (3)
O4—C14	1.447 (3)	C8—H8	0.9301
C1—C2	1.496 (3)	C9—C10	1.383 (4)
C1—C6	1.497 (3)	C9—H9	0.9301
C2—C3	1.549 (3)	C10—C11	1.377 (4)
C2—H2A	0.9700	C10—H10	0.9299
C2—H2B	0.9700	C11—C12	1.387 (3)
C3—C7	1.536 (3)	C11—H11	0.9300
C3—C4	1.561 (3)	C12—H12	0.9300
C4—C13	1.524 (3)	C14—C15	1.469 (4)
C4—C5	1.531 (3)	C14—H14A	0.9700
C4—H4	0.9800	C14—H14B	0.9700
C5—C6	1.530 (3)	C15—H15A	0.9600
C5—H5A	0.9700	C15—H15B	0.9600
C5—H5B	0.9700	C15—H15C	0.9599
C3—O2—H2	107.4 (18)	H6A—C6—H6B	108.0
C13—O4—C14	116.98 (19)	C12—C7—C8	118.5 (2)
O1—C1—C2	122.5 (2)	C12—C7—C3	121.7 (2)
O1—C1—C6	122.9 (2)	C8—C7—C3	119.8 (2)
C2—C1—C6	114.64 (18)	C9—C8—C7	120.2 (3)
C1—C2—C3	113.29 (18)	C9—C8—H8	119.9
C1—C2—H2A	108.9	C7—C8—H8	119.9
C3—C2—H2A	108.9	C10—C9—C8	120.8 (3)
C1—C2—H2B	108.9	C10—C9—H9	119.6
C3—C2—H2B	108.9	C8—C9—H9	119.5
H2A—C2—H2B	107.7	C11—C10—C9	119.1 (3)
O2—C3—C7	112.64 (18)	C11—C10—H10	120.4
O2—C3—C2	108.97 (17)	C9—C10—H10	120.4
C7—C3—C2	108.37 (17)	C10—C11—C12	120.7 (3)
O2—C3—C4	104.75 (17)	C10—C11—H11	119.6
C7—C3—C4	112.49 (16)	C12—C11—H11	119.7
C2—C3—C4	109.53 (17)	C7—C12—C11	120.7 (2)
C13—C4—C5	110.07 (17)	C7—C12—H12	119.7
C13—C4—C3	110.67 (17)	C11—C12—H12	119.5
C5—C4—C3	112.12 (16)	O3—C13—O4	123.5 (2)
C13—C4—H4	107.9	O3—C13—C4	125.2 (2)
C5—C4—H4	108.0	O4—C13—C4	111.24 (18)
C3—C4—H4	107.9	O4—C14—C15	108.4 (2)
C6—C5—C4	111.81 (19)	O4—C14—H14A	110.2
C6—C5—H5A	109.2	C15—C14—H14A	110.2
C4—C5—H5A	109.2	O4—C14—H14B	109.8
C6—C5—H5B	109.3	C15—C14—H14B	109.8
C4—C5—H5B	109.3	H14A—C14—H14B	108.4
H5A—C5—H5B	107.9	C14—C15—H15A	109.3
C1—C6—C5	110.90 (18)	C14—C15—H15B	109.4
C1—C6—H6A	109.4	H15A—C15—H15B	109.5
C5—C6—H6A	109.5	C14—C15—H15C	109.7
C1—C6—H6B	109.5	H15A—C15—H15C	109.5
C5—C6—H6B	109.4	H15B—C15—H15C	109.5
O1—C1—C2—C3	128.3 (2)	O2—C3—C7—C8	−178.07 (19)
C6—C1—C2—C3	−52.6 (3)	C2—C3—C7—C8	−57.4 (2)
C1—C2—C3—O2	−63.5 (2)	C4—C3—C7—C8	63.8 (3)
C1—C2—C3—C7	173.60 (19)	C12—C7—C8—C9	0.1 (3)
C1—C2—C3—C4	50.5 (3)	C3—C7—C8—C9	178.8 (2)
O2—C3—C4—C13	−59.0 (2)	C7—C8—C9—C10	0.0 (4)
C7—C3—C4—C13	63.7 (2)	C8—C9—C10—C11	0.2 (4)
C2—C3—C4—C13	−175.72 (18)	C9—C10—C11—C12	−0.5 (4)
O2—C3—C4—C5	64.3 (2)	C8—C7—C12—C11	−0.4 (3)
C7—C3—C4—C5	−173.00 (18)	C3—C7—C12—C11	−179.1 (2)
C2—C3—C4—C5	−52.4 (2)	C10—C11—C12—C7	0.6 (4)
C13—C4—C5—C6	179.02 (19)	C14—O4—C13—O3	−6.8 (3)
C3—C4—C5—C6	55.4 (2)	C14—O4—C13—C4	172.6 (2)
O1—C1—C6—C5	−127.8 (2)	C5—C4—C13—O3	−18.3 (3)
C2—C1—C6—C5	53.1 (3)	C3—C4—C13—O3	106.2 (2)
C4—C5—C6—C1	−54.1 (3)	C5—C4—C13—O4	162.27 (18)
O2—C3—C7—C12	0.6 (3)	C3—C4—C13—O4	−73.2 (2)
C2—C3—C7—C12	121.2 (2)	C13—O4—C14—C15	−166.0 (2)
C4—C3—C7—C12	−117.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82 (3)	2.06 (3)	2.874 (2)	174 (2)
C6—H6A···O3^ii	0.97	2.78	3.569 (3)	139
C8—H8···O3^ii	0.93	2.74	3.619 (3)	158
C5—H5A···O2^ii	0.97	2.84	3.535 (3)	129
C4—H4···O3^ii	0.98	2.44	3.351 (3)	155

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+3/2.