(1R*,2R*,3S*,4R*)-Diethyl 4-hy­droxy-4-methyl-2-(4-methyl­phen­yl)-6-oxo­cyclo­hexane-1,3-di­carboxyl­ate

Ismiev, A.I.; Gadirova, N.A.; Hajiyeva, K.E.; Askerov, R.K.; Potekhin, K.A.

doi:10.1107/S1600536813009872

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o734

https://doi.org/10.1107/S1600536813009872

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(1R,2R,3S,4R)-Diethyl 4-hydroxy-4-methyl-2-(4-methylphenyl)-6-oxocyclohexane-1,3-dicarboxylate

Arif I. Ismiev,^a Narmina A. Gadirova,^a ^* Kushvar E. Hajiyeva,^a Rizvan K. Askerov ^a and Konstantin A. Potekhin ^b

^aBaku State University, Z. Khalilov St 23, Baku AZ-1148, Azerbaijan, and ^bVladimir State University, Qor'ky St. 87, Vladimir 600000, Russian Federation
^*Correspondence e-mail: kushvarlab7@gmail.com

(Received 2 January 2013; accepted 10 April 2013; online 13 April 2013)

The title compound, C₂₀H₂₆O₆, is chiral and crystallizes as a racemate: the relative configuration of the stereogenic centres is 1R*,2R*,3S*,4R*. The cyclohexane ring has a chair conformation. The ethyl fragment of the ethoxycarbonyl group in the 3-position is disordered over two sets of sites in a 0.650 (6):0.350 (6) ratio. The hydroxy group acts as a bifurcated hydrogen-bond donor, forming both intra- and intermolecular hydrogen bonds with ester carbonyl O atoms. The intermolecular hydrogen bonds form inversion dimers in the crystal.

Related literature

For applications of related compounds as synthetic intermediates, see: Gein et al. (2003 , 2004 ); Sorokin et al. (2000 ).

Experimental

Crystal data

C₂₀H₂₆O₆
M_r = 362.41
Triclinic, $[P \overline 1]$
a = 5.8062 (4) Å
b = 9.9267 (7) Å
c = 18.4548 (13) Å
α = 103.281 (2)°
β = 92.490 (2)°
γ = 104.741 (2)°
V = 995.26 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.974, T_max = 0.983
10589 measured reflections
4344 independent reflections
2735 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.141
S = 1.01
4344 reflections
245 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O1	0.91 (4)	2.28 (4)	2.884 (2)	124 (3)
O6—H6⋯O1ⁱ	0.91 (4)	2.28 (4)	3.066 (2)	145 (3)
Symmetry code: (i) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813009872/fy2087sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009872/fy2087Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009872/fy2087Isup3.cml

checkCIF report

Comment top

The relative arrangement of functional groups in polyfunctional diethoxycarbonyl substituted cyclohexane β-ketols renders them favorable intermediates for the construction of enamines and nitrogen heterocyclic compounds (Gein et al., 2003; Gein et al., 2004; Sorokin et al., 2000). From our point of view, it is important to determine the molecular crystal structure of the initial β-ketols to aid the exploration of heterocyclization reactions.

Fig. 1 shows the molecular structure of title compound (I) C₂₀H₂₆O₆. The cyclohexane ring has a chair conformation (Fig. 2). Four atoms of the cyclohexane ring, C2, C3, C5 and C6 are located on the same plane [r.m.s deviation = 0.011 (2) Å], while C1 [deviation = 0.617 (2) Å] and C4 [deviation = -0.698 (2) Å] deviate from the plane. The ethyl fragment of the ethoxycarbonyl group at the position of C3 is disordered over two sets of sites in a 0.650 (6):0.350 (6) ratio. The OH group participates in the formation of both intramolecular and intermolecular hydrogen bonds. The intermolecular hydrogen bonds form centrosymmetric dimers. These dimers form stacks in the direction of the axis a (Fig. 3). The stacking of dimers is governed by van der Waals interactions.

Related literature top

For applications of related compounds as synthetic intermediates, see: Gein et al. (2003, 2004); Sorokin et al. (2000).

Experimental top

4-methyl benzaldehyde (10 mmol) and acetoacetic ester (20 mmol) were dissolved in 20 ml ethanol. 1 ml piperidine was added to the reaction mixture. After 48 h the obtained crystals were filtered and washed with ethanol. The crystals were dissolved in ethanol (50 ml) and recrystallized by slow solvent evaporation to yield the crystals of the title compound suitable for X-ray analysis.

Structure description top

For applications of related compounds as synthetic intermediates, see: Gein et al. (2003, 2004); Sorokin et al. (2000).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. Perspective view of the dimer. H bonds are shown as a dashed lines. H atoms that not involved in the formation of hydrogen bonds are not shown.
	Fig. 3. Stacking of the dimers in the crystal lattice.

Diethyl 4-hydroxy-4-methyl-2-(4-methylphenyl)-6-oxocyclohexane-1,3-dicarboxylate top

Crystal data top

C₂₀H₂₆O₆	Z = 2
M_r = 362.41	F(000) = 388
Triclinic, P1	D_x = 1.209 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8062 (4) Å	Cell parameters from 2311 reflections
b = 9.9267 (7) Å	θ = 2.2–24.0°
c = 18.4548 (13) Å	µ = 0.09 mm⁻¹
α = 103.281 (2)°	T = 296 K
β = 92.490 (2)°	Prism, colourless
γ = 104.741 (2)°	0.30 × 0.20 × 0.20 mm
V = 995.26 (12) Å³

Data collection top

Bruker APEXII CCD diffractometer	4344 independent reflections
Radiation source: fine-focus sealed tube	2735 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→7
T_min = 0.974, T_max = 0.983	k = −12→12
10589 measured reflections	l = −23→23

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)] = 0.053	Hydrogen site location: difference Fourier map
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0532P)² + 0.330P] where P = (F_o² + 2F_c²)/3
4344 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.30 e Å⁻³
4 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₀H₂₆O₆	γ = 104.741 (2)°
M_r = 362.41	V = 995.26 (12) Å³
Triclinic, P1	Z = 2
a = 5.8062 (4) Å	Mo Kα radiation
b = 9.9267 (7) Å	µ = 0.09 mm⁻¹
c = 18.4548 (13) Å	T = 296 K
α = 103.281 (2)°	0.30 × 0.20 × 0.20 mm
β = 92.490 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4344 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2735 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.983	R_int = 0.024
10589 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	4 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.30 e Å⁻³
4344 reflections	Δρ_min = −0.28 e Å⁻³
245 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.4611 (3)	−0.07429 (19)	0.06812 (9)	0.0807 (6)
O2	0.1412 (3)	−0.13134 (16)	0.12814 (9)	0.0695 (5)
O3	1.0827 (2)	0.24372 (16)	0.31384 (8)	0.0568 (4)
O4	0.8797 (3)	0.31533 (17)	0.40878 (8)	0.0611 (4)
O5	0.8906 (3)	0.48221 (18)	0.26673 (11)	0.0808 (6)
O6	0.6651 (3)	0.23247 (18)	0.09792 (9)	0.0554 (4)
H6	0.628 (6)	0.154 (4)	0.058 (2)	0.131 (14)*
C1	0.6833 (3)	0.2564 (2)	0.28710 (10)	0.0416 (4)
H1A	0.5523	0.2588	0.3187	0.050*
C2	0.6142 (3)	0.10970 (19)	0.22851 (10)	0.0394 (4)
H2A	0.7510	0.1038	0.1998	0.047*
C3	0.4002 (3)	0.1013 (2)	0.17338 (11)	0.0434 (5)
H3A	0.2620	0.1059	0.2015	0.052*
C4	0.4528 (3)	0.2273 (2)	0.13498 (11)	0.0476 (5)
C5	0.5117 (4)	0.3687 (2)	0.19497 (12)	0.0544 (5)
H5A	0.5521	0.4481	0.1713	0.065*
H5B	0.3715	0.3751	0.2208	0.065*
C6	0.7152 (4)	0.3814 (2)	0.25046 (12)	0.0505 (5)
C7	0.3412 (4)	−0.0423 (2)	0.11719 (12)	0.0518 (5)
C8	0.0451 (13)	−0.2768 (4)	0.0822 (3)	0.1013 (17)	0.650 (6)
H8A	0.0897	−0.2839	0.0317	0.122*	0.650 (6)
H8B	−0.1283	−0.3060	0.0800	0.122*	0.650 (6)
C9	0.1545 (10)	−0.3702 (5)	0.1203 (3)	0.1013 (17)	0.650 (6)
H9A	0.0983	−0.4686	0.0922	0.152*	0.650 (6)
H9B	0.1082	−0.3618	0.1701	0.152*	0.650 (6)
H9C	0.3259	−0.3389	0.1227	0.152*	0.650 (6)
C8A	0.1229 (14)	−0.2769 (5)	0.0834 (5)	0.062 (3)*	0.350 (6)
H8AA	0.2699	−0.3026	0.0926	0.074*	0.350 (6)
H8AB	0.0984	−0.2809	0.0305	0.074*	0.350 (6)
C9A	−0.0872 (18)	−0.3816 (10)	0.1050 (6)	0.114 (4)*	0.350 (6)
H9AA	−0.0989	−0.4776	0.0767	0.171*	0.350 (6)
H9AB	−0.2325	−0.3570	0.0945	0.171*	0.350 (6)
H9AC	−0.0626	−0.3761	0.1575	0.171*	0.350 (6)
C10	0.9053 (4)	0.2708 (2)	0.33654 (11)	0.0439 (5)
C11	1.0701 (5)	0.3137 (3)	0.46185 (14)	0.0761 (8)
H11A	1.0708	0.3809	0.5093	0.091*
H11B	1.2236	0.3434	0.4431	0.091*
C12	1.0331 (6)	0.1658 (3)	0.47313 (16)	0.0921 (9)
H12A	1.1512	0.1671	0.5115	0.138*
H12B	1.0485	0.1014	0.4272	0.138*
H12C	0.8760	0.1339	0.4879	0.138*
C13	0.5667 (3)	−0.01238 (19)	0.26723 (10)	0.0394 (4)
C14	0.3813 (4)	−0.0336 (2)	0.31157 (12)	0.0556 (6)
H14A	0.2828	0.0279	0.3177	0.067*
C15	0.3402 (4)	−0.1444 (3)	0.34675 (13)	0.0616 (6)
H15A	0.2136	−0.1565	0.3759	0.074*
C16	0.4826 (4)	−0.2382 (2)	0.33975 (12)	0.0537 (5)
C17	0.6670 (4)	−0.2166 (2)	0.29575 (13)	0.0583 (6)
H17A	0.7665	−0.2775	0.2901	0.070*
C18	0.7080 (4)	−0.1061 (2)	0.25972 (12)	0.0504 (5)
H18A	0.8332	−0.0950	0.2299	0.060*
C19	0.4324 (5)	−0.3606 (3)	0.37778 (15)	0.0763 (8)
H19A	0.5673	−0.4000	0.3769	0.114*
H19B	0.2928	−0.4339	0.3519	0.114*
H19C	0.4052	−0.3255	0.4288	0.114*
C20	0.2422 (4)	0.2159 (3)	0.07980 (14)	0.0680 (7)
H20A	0.2770	0.2975	0.0585	0.102*
H20B	0.1014	0.2137	0.1054	0.102*
H20C	0.2152	0.1293	0.0407	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0936 (13)	0.0774 (12)	0.0587 (10)	0.0147 (10)	0.0294 (10)	−0.0019 (9)
O2	0.0692 (11)	0.0619 (10)	0.0632 (10)	−0.0041 (8)	0.0070 (8)	0.0117 (8)
O3	0.0440 (8)	0.0673 (10)	0.0644 (10)	0.0212 (7)	0.0064 (7)	0.0197 (8)
O4	0.0712 (10)	0.0678 (10)	0.0452 (8)	0.0292 (8)	−0.0008 (7)	0.0059 (7)
O5	0.0744 (12)	0.0503 (10)	0.1131 (15)	0.0027 (9)	−0.0191 (10)	0.0327 (10)
O6	0.0469 (8)	0.0681 (10)	0.0568 (9)	0.0153 (7)	0.0161 (7)	0.0252 (8)
C1	0.0396 (10)	0.0436 (11)	0.0444 (11)	0.0158 (8)	0.0069 (9)	0.0115 (9)
C2	0.0366 (10)	0.0442 (11)	0.0411 (10)	0.0150 (8)	0.0085 (8)	0.0125 (8)
C3	0.0371 (10)	0.0528 (12)	0.0425 (11)	0.0145 (9)	0.0088 (8)	0.0132 (9)
C4	0.0410 (11)	0.0609 (13)	0.0480 (11)	0.0189 (9)	0.0079 (9)	0.0214 (10)
C5	0.0567 (13)	0.0541 (13)	0.0635 (14)	0.0258 (10)	0.0082 (11)	0.0244 (11)
C6	0.0521 (12)	0.0430 (12)	0.0590 (13)	0.0179 (10)	0.0044 (10)	0.0123 (10)
C7	0.0535 (13)	0.0589 (13)	0.0417 (11)	0.0127 (11)	0.0041 (10)	0.0132 (10)
C8	0.124 (4)	0.071 (2)	0.085 (3)	−0.003 (2)	−0.022 (2)	0.0108 (17)
C9	0.124 (4)	0.071 (2)	0.085 (3)	−0.003 (2)	−0.022 (2)	0.0108 (17)
C10	0.0479 (12)	0.0353 (10)	0.0490 (12)	0.0122 (9)	0.0044 (9)	0.0105 (9)
C11	0.095 (2)	0.0757 (18)	0.0550 (14)	0.0293 (15)	−0.0175 (14)	0.0088 (13)
C12	0.127 (3)	0.094 (2)	0.0652 (17)	0.0392 (19)	−0.0012 (17)	0.0311 (16)
C13	0.0374 (10)	0.0405 (10)	0.0405 (10)	0.0121 (8)	0.0039 (8)	0.0087 (8)
C14	0.0566 (13)	0.0656 (14)	0.0604 (13)	0.0299 (11)	0.0210 (11)	0.0293 (11)
C15	0.0578 (14)	0.0756 (16)	0.0618 (14)	0.0191 (12)	0.0189 (11)	0.0344 (13)
C16	0.0566 (13)	0.0474 (12)	0.0530 (13)	0.0046 (10)	−0.0064 (11)	0.0175 (10)
C17	0.0549 (13)	0.0462 (12)	0.0780 (16)	0.0190 (10)	0.0040 (12)	0.0183 (11)
C18	0.0463 (11)	0.0440 (11)	0.0630 (13)	0.0146 (9)	0.0134 (10)	0.0138 (10)
C19	0.0884 (19)	0.0631 (16)	0.0767 (17)	0.0067 (14)	−0.0060 (15)	0.0347 (14)
C20	0.0573 (14)	0.0904 (18)	0.0661 (15)	0.0255 (13)	0.0000 (12)	0.0339 (14)

Geometric parameters (Å, º) top

O1—C7	1.200 (2)	C9—H9C	0.9600
O2—C7	1.323 (3)	C8A—C9A	1.522 (4)
O2—C8	1.449 (3)	C8A—H8AA	0.9700
O2—C8A	1.465 (4)	C8A—H8AB	0.9700
O3—C10	1.198 (2)	C9A—H9AA	0.9600
O4—C10	1.332 (2)	C9A—H9AB	0.9600
O4—C11	1.450 (3)	C9A—H9AC	0.9600
O5—C6	1.203 (3)	C11—C12	1.493 (4)
O6—C4	1.431 (2)	C11—H11A	0.9700
O6—H6	0.91 (4)	C11—H11B	0.9700
C1—C10	1.503 (3)	C12—H12A	0.9600
C1—C6	1.520 (3)	C12—H12B	0.9600
C1—C2	1.547 (3)	C12—H12C	0.9600
C1—H1A	0.9800	C13—C18	1.377 (3)
C2—C13	1.517 (3)	C13—C14	1.383 (3)
C2—C3	1.544 (3)	C14—C15	1.377 (3)
C2—H2A	0.9800	C14—H14A	0.9300
C3—C7	1.505 (3)	C15—C16	1.382 (3)
C3—C4	1.546 (3)	C15—H15A	0.9300
C3—H3A	0.9800	C16—C17	1.375 (3)
C4—C20	1.521 (3)	C16—C19	1.511 (3)
C4—C5	1.524 (3)	C17—C18	1.385 (3)
C5—C6	1.490 (3)	C17—H17A	0.9300
C5—H5A	0.9700	C18—H18A	0.9300
C5—H5B	0.9700	C19—H19A	0.9600
C8—C9	1.522 (4)	C19—H19B	0.9600
C8—H8A	0.9700	C19—H19C	0.9600
C8—H8B	0.9700	C20—H20A	0.9600
C9—H9A	0.9600	C20—H20B	0.9600
C9—H9B	0.9600	C20—H20C	0.9600

C7—O2—C8	123.5 (4)	O2—C8A—H8AB	109.9
C7—O2—C8A	109.3 (3)	C9A—C8A—H8AB	109.9
C10—O4—C11	116.33 (18)	H8AA—C8A—H8AB	108.3
C4—O6—H6	106 (2)	C8A—C9A—H9AA	109.5
C10—C1—C6	111.07 (16)	C8A—C9A—H9AB	109.5
C10—C1—C2	110.21 (14)	H9AA—C9A—H9AB	109.5
C6—C1—C2	111.87 (16)	C8A—C9A—H9AC	109.5
C10—C1—H1A	107.8	H9AA—C9A—H9AC	109.5
C6—C1—H1A	107.8	H9AB—C9A—H9AC	109.5
C2—C1—H1A	107.8	O3—C10—O4	124.06 (19)
C13—C2—C3	113.00 (15)	O3—C10—C1	124.13 (18)
C13—C2—C1	110.32 (15)	O4—C10—C1	111.80 (17)
C3—C2—C1	109.93 (14)	O4—C11—C12	109.8 (2)
C13—C2—H2A	107.8	O4—C11—H11A	109.7
C3—C2—H2A	107.8	C12—C11—H11A	109.7
C1—C2—H2A	107.8	O4—C11—H11B	109.7
C7—C3—C2	107.99 (16)	C12—C11—H11B	109.7
C7—C3—C4	111.78 (16)	H11A—C11—H11B	108.2
C2—C3—C4	111.96 (15)	C11—C12—H12A	109.5
C7—C3—H3A	108.3	C11—C12—H12B	109.5
C2—C3—H3A	108.3	H12A—C12—H12B	109.5
C4—C3—H3A	108.3	C11—C12—H12C	109.5
O6—C4—C20	110.23 (17)	H12A—C12—H12C	109.5
O6—C4—C5	104.60 (17)	H12B—C12—H12C	109.5
C20—C4—C5	110.88 (18)	C18—C13—C14	117.48 (18)
O6—C4—C3	110.68 (15)	C18—C13—C2	121.02 (17)
C20—C4—C3	111.32 (17)	C14—C13—C2	121.50 (16)
C5—C4—C3	108.92 (16)	C15—C14—C13	121.1 (2)
C6—C5—C4	111.90 (16)	C15—C14—H14A	119.5
C6—C5—H5A	109.2	C13—C14—H14A	119.5
C4—C5—H5A	109.2	C14—C15—C16	121.7 (2)
C6—C5—H5B	109.2	C14—C15—H15A	119.2
C4—C5—H5B	109.2	C16—C15—H15A	119.2
H5A—C5—H5B	107.9	C17—C16—C15	117.14 (19)
O5—C6—C5	123.9 (2)	C17—C16—C19	121.9 (2)
O5—C6—C1	121.56 (19)	C15—C16—C19	120.9 (2)
C5—C6—C1	114.57 (18)	C16—C17—C18	121.5 (2)
O1—C7—O2	123.2 (2)	C16—C17—H17A	119.3
O1—C7—C3	124.5 (2)	C18—C17—H17A	119.3
O2—C7—C3	112.31 (18)	C13—C18—C17	121.2 (2)
O2—C8—C9	105.3 (3)	C13—C18—H18A	119.4
O2—C8—H8A	110.7	C17—C18—H18A	119.4
C9—C8—H8A	110.7	C16—C19—H19A	109.5
O2—C8—H8B	110.7	C16—C19—H19B	109.5
C9—C8—H8B	110.7	H19A—C19—H19B	109.5
H8A—C8—H8B	108.8	C16—C19—H19C	109.5
C8—C9—H9A	109.5	H19A—C19—H19C	109.5
C8—C9—H9B	109.5	H19B—C19—H19C	109.5
H9A—C9—H9B	109.5	C4—C20—H20A	109.5
C8—C9—H9C	109.5	C4—C20—H20B	109.5
H9A—C9—H9C	109.5	H20A—C20—H20B	109.5
H9B—C9—H9C	109.5	C4—C20—H20C	109.5
O2—C8A—C9A	108.8 (6)	H20A—C20—H20C	109.5
O2—C8A—H8AA	109.9	H20B—C20—H20C	109.5
C9A—C8A—H8AA	109.9

C10—C1—C2—C13	59.94 (19)	C4—C3—C7—O1	51.1 (3)
C6—C1—C2—C13	−175.97 (15)	C2—C3—C7—O2	106.96 (19)
C10—C1—C2—C3	−174.79 (15)	C4—C3—C7—O2	−129.45 (18)
C6—C1—C2—C3	−50.7 (2)	C7—O2—C8—C9	90.5 (5)
C13—C2—C3—C7	−56.8 (2)	C8A—O2—C8—C9	50.2 (14)
C1—C2—C3—C7	179.47 (16)	C7—O2—C8A—C9A	171.7 (6)
C13—C2—C3—C4	179.72 (15)	C8—O2—C8A—C9A	−43.2 (13)
C1—C2—C3—C4	56.0 (2)	C11—O4—C10—O3	−7.4 (3)
C7—C3—C4—O6	−65.3 (2)	C11—O4—C10—C1	171.67 (18)
C2—C3—C4—O6	56.0 (2)	C6—C1—C10—O3	−77.4 (2)
C7—C3—C4—C20	57.6 (2)	C2—C1—C10—O3	47.1 (3)
C2—C3—C4—C20	178.94 (17)	C6—C1—C10—O4	103.56 (19)
C7—C3—C4—C5	−179.81 (16)	C2—C1—C10—O4	−131.89 (17)
C2—C3—C4—C5	−58.5 (2)	C10—O4—C11—C12	−82.2 (3)
O6—C4—C5—C6	−62.1 (2)	C3—C2—C13—C18	120.07 (19)
C20—C4—C5—C6	179.10 (18)	C1—C2—C13—C18	−116.4 (2)
C3—C4—C5—C6	56.3 (2)	C3—C2—C13—C14	−60.3 (2)
C4—C5—C6—O5	127.0 (2)	C1—C2—C13—C14	63.3 (2)
C4—C5—C6—C1	−54.1 (2)	C18—C13—C14—C15	0.0 (3)
C10—C1—C6—O5	−6.5 (3)	C2—C13—C14—C15	−179.7 (2)
C2—C1—C6—O5	−130.1 (2)	C13—C14—C15—C16	0.4 (4)
C10—C1—C6—C5	174.63 (17)	C14—C15—C16—C17	−0.3 (3)
C2—C1—C6—C5	51.0 (2)	C14—C15—C16—C19	−179.0 (2)
C8—O2—C7—O1	0.0 (4)	C15—C16—C17—C18	−0.3 (3)
C8A—O2—C7—O1	12.1 (5)	C19—C16—C17—C18	178.5 (2)
C8—O2—C7—C3	−179.5 (3)	C14—C13—C18—C17	−0.5 (3)
C8A—O2—C7—C3	−167.4 (4)	C2—C13—C18—C17	179.17 (19)
C2—C3—C7—O1	−72.5 (3)	C16—C17—C18—C13	0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O1	0.91 (4)	2.28 (4)	2.884 (2)	124 (3)
O6—H6···O1ⁱ	0.91 (4)	2.28 (4)	3.066 (2)	145 (3)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆O₆
M_r	362.41
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.8062 (4), 9.9267 (7), 18.4548 (13)
α, β, γ (°)	103.281 (2), 92.490 (2), 104.741 (2)
V (Å³)	995.26 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.974, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	10589, 4344, 2735
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.141, 1.01
No. of reflections	4344
No. of parameters	245
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O1	0.91 (4)	2.28 (4)	2.884 (2)	124 (3)
O6—H6···O1ⁱ	0.91 (4)	2.28 (4)	3.066 (2)	145 (3)

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

We thank Baku State University and Vladimir State University for supporting this study.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gein, V. L., Gein, N. V. & Krivenko, A. P. (2003). Russ. J. Gen. Chem. 73, 490–491. Web of Science CrossRef CAS Google Scholar
Gein, V. L., Gein, N. V., Potemkin, K. D. & Krivenko, A. P. (2004). Russ. J. Gen. Chem. 74, 1564–1568. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sorokin, V. V., Grigor'ev, A. V., Ramazanov, A. K. & Krivenko, A. P. (2000). Russ. J. Org. Chem. 36, 781–784. CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1R*,2R*,3S*,4R*)-Di­ethyl 4-hy­dr­oxy-4-methyl-2-(4-methyl­phen­yl)-6-oxo­cyclo­hexane-1,3-di­carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1R,2R,3S,4R)-Diethyl 4-hydroxy-4-methyl-2-(4-methylphenyl)-6-oxocyclohexane-1,3-dicarboxylate