Diethyl 4-hy-droxy-4-methyl-6-oxo-2-phenyl-cyclo-hexane-1,3-dicarboxyl-ate.

In the title mol-ecule, C(19)H(24)O(6), the cyclo-hexa-none ring adopts a chair conformation. The dihedral angle between the phenyl ring and the best plane through the six atoms of the cyclo-hexa-none ring is 89.68 (7)°. In the crystal structure, mol-ecules are linked via pairs of inter-molecular O-H⋯O hydrogen bonds into centrosymmetric dimers and these dimers are connected by C-H⋯O inter-actions into columns down the a axis.

Related literature

For the applications of phenyl­cylcohexane, see: Adly et al. (2004 ▶); Pohl et al. (1977 ▶); Chu et al. (2005 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C19H24O6

M = 348.38

Monoclinic,

a = 5.792 (2) Å

b = 15.766 (6) Å

c = 20.031 (7) Å

β = 98.531 (10)°

V = 1808.9 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.40 × 0.10 × 0.06 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.994

37474 measured reflections

5256 independent reflections

3644 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.122

S = 1.05

5256 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025018/bt5276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025018/bt5276Isup2.hkl

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

C19H24O6	F(000) = 744
Mr = 348.38	Dx = 1.279 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4276 reflections
a = 5.792 (2) Å	θ = 2.4–25.6°
b = 15.766 (6) Å	µ = 0.10 mm−1
c = 20.031 (7) Å	T = 100 K
β = 98.531 (10)°	Needle, colourless
V = 1808.9 (11) Å3	0.40 × 0.10 × 0.06 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	5256 independent reflections
Radiation source: fine-focus sealed tube	3644 reflections with I > 2σ(I)
graphite	Rint = 0.075
φ and ω scans	θmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.963, Tmax = 0.994	k = −22→22
37474 measured reflections	l = −25→28

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0484P)2 + 0.4474P] where P = (Fo2 + 2Fc2)/3
5256 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.01230 (19)	0.45072 (6)	0.06556 (6)	0.0303 (2)
O2	−0.26845 (17)	0.40000 (6)	0.12086 (5)	0.0264 (2)
O3	0.47676 (16)	0.15467 (6)	0.04607 (6)	0.0272 (2)
O4	0.24998 (17)	0.04265 (6)	0.06139 (5)	0.0249 (2)
O5	0.1168 (2)	0.14395 (7)	−0.08748 (6)	0.0370 (3)
O6	0.03208 (17)	0.36001 (7)	−0.05989 (5)	0.0249 (2)
C1	−0.1446 (2)	0.31138 (8)	0.03806 (7)	0.0188 (3)
H1A	−0.2822	0.2817	0.0494	0.023*
C2	−0.1754 (2)	0.32386 (9)	−0.03951 (7)	0.0212 (3)
C3	−0.1990 (2)	0.23718 (9)	−0.07382 (7)	0.0247 (3)
H3A	−0.3412	0.2101	−0.0645	0.030*
H3B	−0.2112	0.2447	−0.1223	0.030*
C4	0.0059 (2)	0.18060 (9)	−0.04977 (7)	0.0232 (3)
C5	0.0596 (2)	0.17099 (8)	0.02663 (7)	0.0183 (3)
H5A	−0.0662	0.1379	0.0417	0.022*
C6	0.0736 (2)	0.25755 (8)	0.06335 (7)	0.0182 (3)
H6A	0.2101	0.2878	0.0517	0.022*
C7	0.1109 (2)	0.24444 (8)	0.13937 (7)	0.0195 (3)
C8	−0.0573 (2)	0.20405 (9)	0.17164 (7)	0.0240 (3)
H8A	−0.1954	0.1852	0.1464	0.029*
C9	−0.0195 (3)	0.19190 (10)	0.24098 (8)	0.0296 (3)
H9A	−0.1327	0.1651	0.2619	0.036*
C10	0.1857 (3)	0.21942 (11)	0.27934 (8)	0.0328 (4)
H10A	0.2105	0.2113	0.3258	0.039*
C11	0.3533 (3)	0.25901 (11)	0.24780 (8)	0.0326 (4)
H11A	0.4917	0.2774	0.2733	0.039*
C12	0.3165 (2)	0.27152 (9)	0.17833 (7)	0.0251 (3)
H12A	0.4305	0.2983	0.1577	0.030*
C13	−0.1227 (2)	0.39519 (9)	0.07513 (7)	0.0217 (3)
C14	−0.2384 (3)	0.47213 (10)	0.16704 (8)	0.0304 (3)
H14A	−0.3797	0.4802	0.1869	0.036*
H14B	−0.2117	0.5231	0.1422	0.036*
C15	−0.0354 (3)	0.45777 (11)	0.22215 (9)	0.0378 (4)
H15A	−0.0292	0.5027	0.2547	0.057*
H15B	0.1070	0.4569	0.2030	0.057*
H15C	−0.0547	0.4045	0.2439	0.057*
C16	0.2866 (2)	0.12288 (8)	0.04565 (7)	0.0191 (3)
C17	0.4559 (3)	−0.00928 (10)	0.08439 (8)	0.0283 (3)
H17A	0.5945	0.0184	0.0730	0.034*
H17B	0.4407	−0.0640	0.0621	0.034*
C18	0.4780 (4)	−0.02101 (15)	0.15860 (9)	0.0539 (6)
H18A	0.6084	−0.0574	0.1735	0.081*
H18B	0.3378	−0.0463	0.1697	0.081*
H18C	0.5022	0.0331	0.1806	0.081*
C19	−0.3862 (2)	0.37923 (10)	−0.06405 (8)	0.0275 (3)
H19A	−0.4048	0.3838	−0.1123	0.041*
H19B	−0.3631	0.4347	−0.0444	0.041*
H19C	−0.5236	0.3541	−0.0509	0.041*
H1O6	0.033 (5)	0.422 (2)	−0.0480 (14)	0.106 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0355 (6)	0.0239 (5)	0.0336 (6)	−0.0066 (4)	0.0123 (5)	−0.0006 (4)
O2	0.0255 (5)	0.0263 (5)	0.0293 (6)	0.0004 (4)	0.0102 (4)	−0.0018 (4)
O3	0.0194 (5)	0.0234 (5)	0.0391 (6)	−0.0008 (4)	0.0051 (4)	−0.0006 (4)
O4	0.0233 (5)	0.0203 (5)	0.0306 (6)	0.0012 (4)	0.0025 (4)	0.0047 (4)
O5	0.0469 (7)	0.0399 (7)	0.0246 (6)	0.0141 (5)	0.0068 (5)	−0.0014 (5)
O6	0.0225 (5)	0.0263 (5)	0.0267 (6)	−0.0019 (4)	0.0066 (4)	0.0029 (4)
C1	0.0153 (6)	0.0199 (6)	0.0210 (7)	−0.0006 (5)	0.0017 (5)	0.0017 (5)
C2	0.0172 (6)	0.0231 (7)	0.0226 (7)	0.0010 (5)	0.0003 (5)	0.0032 (5)
C3	0.0253 (7)	0.0254 (7)	0.0215 (7)	−0.0002 (5)	−0.0029 (5)	0.0021 (6)
C4	0.0261 (7)	0.0204 (7)	0.0226 (7)	−0.0017 (5)	0.0014 (5)	0.0001 (5)
C5	0.0168 (6)	0.0193 (6)	0.0182 (6)	−0.0006 (5)	0.0011 (5)	0.0016 (5)
C6	0.0159 (6)	0.0186 (6)	0.0200 (6)	−0.0002 (5)	0.0018 (5)	0.0009 (5)
C7	0.0193 (6)	0.0190 (6)	0.0199 (7)	0.0032 (5)	0.0017 (5)	0.0003 (5)
C8	0.0229 (7)	0.0255 (7)	0.0233 (7)	0.0009 (5)	0.0027 (5)	0.0025 (6)
C9	0.0325 (8)	0.0326 (8)	0.0249 (8)	0.0052 (6)	0.0079 (6)	0.0052 (6)
C10	0.0389 (9)	0.0399 (9)	0.0188 (7)	0.0123 (7)	0.0014 (6)	0.0011 (7)
C11	0.0287 (8)	0.0418 (9)	0.0247 (8)	0.0059 (6)	−0.0048 (6)	−0.0056 (7)
C12	0.0212 (6)	0.0290 (7)	0.0247 (7)	0.0007 (5)	0.0018 (5)	−0.0032 (6)
C13	0.0199 (6)	0.0221 (7)	0.0232 (7)	0.0026 (5)	0.0037 (5)	0.0040 (5)
C14	0.0346 (8)	0.0249 (8)	0.0334 (9)	0.0059 (6)	0.0106 (6)	−0.0043 (6)
C15	0.0447 (10)	0.0349 (9)	0.0331 (9)	0.0027 (7)	0.0027 (7)	−0.0063 (7)
C16	0.0217 (6)	0.0189 (6)	0.0163 (6)	0.0005 (5)	0.0020 (5)	−0.0018 (5)
C17	0.0283 (7)	0.0228 (7)	0.0335 (8)	0.0079 (6)	0.0040 (6)	0.0057 (6)
C18	0.0586 (12)	0.0717 (14)	0.0302 (10)	0.0307 (11)	0.0024 (9)	0.0099 (9)
C19	0.0214 (7)	0.0293 (8)	0.0299 (8)	0.0048 (6)	−0.0021 (6)	0.0048 (6)

O1—C13	1.2078 (17)	C7—C8	1.3995 (19)
O2—C13	1.3369 (17)	C8—C9	1.387 (2)
O2—C14	1.4599 (18)	C8—H8A	0.9300
O3—C16	1.2088 (16)	C9—C10	1.386 (2)
O4—C16	1.3283 (17)	C9—H9A	0.9300
O4—C17	1.4634 (17)	C10—C11	1.383 (2)
O5—C4	1.2088 (17)	C10—H10A	0.9300
O6—C2	1.4424 (17)	C11—C12	1.390 (2)
O6—H1O6	1.01 (3)	C11—H11A	0.9300
C1—C13	1.512 (2)	C12—H12A	0.9300
C1—C6	1.5442 (18)	C14—C15	1.506 (2)
C1—C2	1.5499 (19)	C14—H14A	0.9700
C1—H1A	0.9800	C14—H14B	0.9700
C2—C19	1.5220 (19)	C15—H15A	0.9600
C2—C3	1.527 (2)	C15—H15B	0.9600
C3—C4	1.505 (2)	C15—H15C	0.9600
C3—H3A	0.9700	C17—C18	1.485 (2)
C3—H3B	0.9700	C17—H17A	0.9700
C4—C5	1.5233 (19)	C17—H17B	0.9700
C5—C16	1.5168 (18)	C18—H18A	0.9600
C5—C6	1.5468 (19)	C18—H18B	0.9600
C5—H5A	0.9800	C18—H18C	0.9600
C6—C7	1.5201 (19)	C19—H19A	0.9600
C6—H6A	0.9800	C19—H19B	0.9600
C7—C12	1.3908 (19)	C19—H19C	0.9600
C13—O2—C14	116.77 (11)	C11—C10—C9	119.38 (14)
C16—O4—C17	117.13 (11)	C11—C10—H10A	120.3
C2—O6—H1O6	106.9 (17)	C9—C10—H10A	120.3
C13—C1—C6	108.32 (11)	C10—C11—C12	120.49 (14)
C13—C1—C2	111.74 (11)	C10—C11—H11A	119.8
C6—C1—C2	111.44 (11)	C12—C11—H11A	119.8
C13—C1—H1A	108.4	C11—C12—C7	120.63 (14)
C6—C1—H1A	108.4	C11—C12—H12A	119.7
C2—C1—H1A	108.4	C7—C12—H12A	119.7
O6—C2—C19	110.12 (11)	O1—C13—O2	123.86 (13)
O6—C2—C3	104.43 (11)	O1—C13—C1	124.38 (12)
C19—C2—C3	110.73 (12)	O2—C13—C1	111.76 (11)
O6—C2—C1	110.92 (10)	O2—C14—C15	110.74 (12)
C19—C2—C1	111.35 (11)	O2—C14—H14A	109.5
C3—C2—C1	109.08 (11)	C15—C14—H14A	109.5
C4—C3—C2	111.87 (11)	O2—C14—H14B	109.5
C4—C3—H3A	109.2	C15—C14—H14B	109.5
C2—C3—H3A	109.2	H14A—C14—H14B	108.1
C4—C3—H3B	109.2	C14—C15—H15A	109.5
C2—C3—H3B	109.2	C14—C15—H15B	109.5
H3A—C3—H3B	107.9	H15A—C15—H15B	109.5
O5—C4—C3	123.37 (13)	C14—C15—H15C	109.5
O5—C4—C5	122.13 (13)	H15A—C15—H15C	109.5
C3—C4—C5	114.48 (12)	H15B—C15—H15C	109.5
C16—C5—C4	110.02 (11)	O3—C16—O4	124.81 (12)
C16—C5—C6	109.83 (10)	O3—C16—C5	123.32 (12)
C4—C5—C6	112.23 (11)	O4—C16—C5	111.88 (11)
C16—C5—H5A	108.2	O4—C17—C18	109.29 (13)
C4—C5—H5A	108.2	O4—C17—H17A	109.8
C6—C5—H5A	108.2	C18—C17—H17A	109.8
C7—C6—C1	113.02 (11)	O4—C17—H17B	109.8
C7—C6—C5	110.25 (11)	C18—C17—H17B	109.8
C1—C6—C5	110.26 (10)	H17A—C17—H17B	108.3
C7—C6—H6A	107.7	C17—C18—H18A	109.5
C1—C6—H6A	107.7	C17—C18—H18B	109.5
C5—C6—H6A	107.7	H18A—C18—H18B	109.5
C12—C7—C8	118.50 (13)	C17—C18—H18C	109.5
C12—C7—C6	120.19 (12)	H18A—C18—H18C	109.5
C8—C7—C6	121.30 (12)	H18B—C18—H18C	109.5
C9—C8—C7	120.55 (13)	C2—C19—H19A	109.5
C9—C8—H8A	119.7	C2—C19—H19B	109.5
C7—C8—H8A	119.7	H19A—C19—H19B	109.5
C10—C9—C8	120.45 (15)	C2—C19—H19C	109.5
C10—C9—H9A	119.8	H19A—C19—H19C	109.5
C8—C9—H9A	119.8	H19B—C19—H19C	109.5
C13—C1—C2—O6	66.12 (14)	C1—C6—C7—C8	60.00 (16)
C6—C1—C2—O6	−55.22 (14)	C5—C6—C7—C8	−63.89 (16)
C13—C1—C2—C19	−56.89 (14)	C12—C7—C8—C9	0.4 (2)
C6—C1—C2—C19	−178.22 (11)	C6—C7—C8—C9	179.40 (13)
C13—C1—C2—C3	−179.39 (11)	C7—C8—C9—C10	−0.2 (2)
C6—C1—C2—C3	59.27 (14)	C8—C9—C10—C11	−0.2 (2)
O6—C2—C3—C4	62.27 (14)	C9—C10—C11—C12	0.3 (2)
C19—C2—C3—C4	−179.24 (12)	C10—C11—C12—C7	0.0 (2)
C1—C2—C3—C4	−56.36 (15)	C8—C7—C12—C11	−0.3 (2)
C2—C3—C4—O5	−128.63 (15)	C6—C7—C12—C11	−179.30 (13)
C2—C3—C4—C5	52.96 (16)	C14—O2—C13—O1	−8.1 (2)
O5—C4—C5—C16	9.17 (18)	C14—O2—C13—C1	170.78 (11)
C3—C4—C5—C16	−172.40 (11)	C6—C1—C13—O1	71.82 (17)
O5—C4—C5—C6	131.79 (14)	C2—C1—C13—O1	−51.30 (17)
C3—C4—C5—C6	−49.77 (15)	C6—C1—C13—O2	−107.10 (12)
C13—C1—C6—C7	56.26 (14)	C2—C1—C13—O2	129.77 (12)
C2—C1—C6—C7	179.57 (11)	C13—O2—C14—C15	−78.28 (17)
C13—C1—C6—C5	−179.85 (10)	C17—O4—C16—O3	3.5 (2)
C2—C1—C6—C5	−56.55 (14)	C17—O4—C16—C5	−176.62 (11)
C16—C5—C6—C7	−61.15 (13)	C4—C5—C16—O3	77.32 (16)
C4—C5—C6—C7	176.13 (10)	C6—C5—C16—O3	−46.70 (17)
C16—C5—C6—C1	173.38 (10)	C4—C5—C16—O4	−102.57 (13)
C4—C5—C6—C1	50.65 (14)	C6—C5—C16—O4	133.41 (12)
C1—C6—C7—C12	−121.02 (14)	C16—O4—C17—C18	104.66 (16)
C5—C6—C7—C12	115.09 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H1O6···O1i	1.01 (3)	2.05 (3)	2.9958 (18)	156 (2)
C1—H1A···O3ii	0.98	2.44	3.323 (2)	150
C8—H8A···O3ii	0.93	2.60	3.493 (2)	162
C12—H12A···O2iii	0.93	2.56	3.468 (2)	166
C19—H19C···O6ii	0.96	2.55	3.396 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H1O6⋯O1i	1.01 (3)	2.05 (3)	2.9958 (18)	156 (2)
C1—H1A⋯O3ii	0.98	2.44	3.323 (2)	150
C8—H8A⋯O3ii	0.93	2.60	3.493 (2)	162
C12—H12A⋯O2iii	0.93	2.56	3.468 (2)	166
C19—H19C⋯O6ii	0.96	2.55	3.396 (2)	146

Symmetry codes: (i) ; (ii) ; (iii) .