Dimethyl 3-phenyl­penta­nedioate

Zhang, P.; Fu, F.; Wang, N.

doi:10.1107/S1600536810041954

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3114

https://doi.org/10.1107/S1600536810041954

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Dimethyl 3-phenylpentanedioate

Peng Zhang,^a Feng Fu ^a ^* and Ni Wang ^a

^aDepartment of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Reaction Engineering, Yan'an University, Shaanxi 716000, People's Republic of China
^*Correspondence e-mail: chemfufeng@126.com

(Received 9 October 2010; accepted 16 October 2010; online 10 November 2010)

In the title compound, C₁₃H₁₆O₄, the terminal carboxylate groups are twisted to each other at a dihedral angle of 23.80 (9)°. Weak intermolecular C—H⋯O hydrogen bonds link the molecules into supramolecular chains along the a axis.

Related literature

For approximately extended structures of carbon skeleton in pentanedioate compounds, see: Fun & Chantrapromma (2009 ); Karadayı (2008 ); Yang et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₆O₄
M_r = 236.26
Triclinic, $[P \overline 1]$
a = 5.7944 (2) Å
b = 8.7668 (3) Å
c = 12.7591 (4) Å
α = 92.609 (2)°
β = 101.979 (2)°
γ = 96.140 (2)°
V = 628.86 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.32 × 0.26 × 0.13 mm

Data collection

Bruker SMART 1000 CCD diffractometer
8883 measured reflections
2207 independent reflections
1839 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.116
S = 1.07
2207 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O4ⁱ	0.97	2.53	3.3987 (19)	149
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810041954/xu5052sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041954/xu5052Isup2.hkl

checkCIF report

Comment top

We attempted to synthesize a Cd^II complex with the mixed ligands using hydrothermal conditions. However we were not successful, and the title ester was unexpectedly obtained. Its structure is reported here.

The molecular structure is shown in Fig 1. The phenyl ring is almost perpendicular to the plane of C7, C8 and C11 atoms with a dihedral angle of 88.945 (6)°. The carbon skeleton of the pentanedioate displays an approximately extended structure, similar to those found in the crystal structures of related compounds (Fun & Chantrapromma, 2009; Karadayı, 2008; Yang et al. 2008). The terminal carboxylate groups are twisted to each other with a dihedal angle of 23.80 (9)°.

In the crystal structure, molecules are linked by C–H···O hydrogen bonds into a one-dimensional chain along the a axis (Table 1).

Related literature top

For approximately extended structures of carbon skeleton in pentanedioate compounds, see: Fun & Chantrapromma (2009); Karadayı (2008); Yang et al. (2008).

Experimental top

All chemicals were of reagent grade quality obtained from commercial sources and used without further purification. An H₂O/CH₃OH (1:1) solution (8.0 ml) containing mixture of Cd(NO₃)₂.6H₂O (0.1 mmol, 0.0308 mg), 3-phenylglutaric acid (0.1 mmol, 0.0208 g), 1,3-di(4-pyridyl)propane (0.05 mmol, 0.0099 g) and NaOH (0.1 mmol) was sealed in a 23 ml Teflon-lined autoclave, heated at 413 K for 3 days and then cooled to room temperature at 5 K min^-1. The colorless crystals were obtained.

Structure description top

In the crystal structure, molecules are linked by C–H···O hydrogen bonds into a one-dimensional chain along the a axis (Table 1).

For approximately extended structures of carbon skeleton in pentanedioate compounds, see: Fun & Chantrapromma (2009); Karadayı (2008); Yang et al. (2008).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. The molecular structure of the title compound, showing the atomic numbering scheme. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. One-dimensional double chain connected by hydrogen bonds in the title complex.

Dimethyl 3-phenylpentanedioate top

Crystal data top

C₁₃H₁₆O₄	Z = 2
M_r = 236.26	F(000) = 252
Triclinic, P1	D_x = 1.248 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7944 (2) Å	Cell parameters from 2207 reflections
b = 8.7668 (3) Å	θ = 1.6–25.0°
c = 12.7591 (4) Å	µ = 0.09 mm⁻¹
α = 92.609 (2)°	T = 296 K
β = 101.979 (2)°	Prism, colorless
γ = 96.140 (2)°	0.32 × 0.26 × 0.13 mm
V = 628.86 (4) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	1839 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 25.0°, θ_min = 1.6°
φ and ω scans	h = −6→6
8883 measured reflections	k = −9→10
2207 independent reflections	l = −15→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0636P)² + 0.0827P] where P = (F_o² + 2F_c²)/3
2207 reflections	(Δ/σ)_max < 0.001
156 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₃H₁₆O₄	γ = 96.140 (2)°
M_r = 236.26	V = 628.86 (4) Å³
Triclinic, P1	Z = 2
a = 5.7944 (2) Å	Mo Kα radiation
b = 8.7668 (3) Å	µ = 0.09 mm⁻¹
c = 12.7591 (4) Å	T = 296 K
α = 92.609 (2)°	0.32 × 0.26 × 0.13 mm
β = 101.979 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1839 reflections with I > 2σ(I)
8883 measured reflections	R_int = 0.020
2207 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.07	Δρ_max = 0.15 e Å⁻³
2207 reflections	Δρ_min = −0.14 e Å⁻³
156 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
C1	0.4786 (2)	0.22914 (15)	0.76660 (10)	0.0402 (3)
C2	0.6254 (3)	0.26207 (18)	0.69556 (13)	0.0551 (4)
H2	0.7299	0.1932	0.6833	0.066*
C3	0.6182 (3)	0.3963 (2)	0.64272 (13)	0.0635 (5)
H3	0.7184	0.4169	0.5955	0.076*
C4	0.4658 (3)	0.49892 (18)	0.65906 (13)	0.0579 (4)
H4	0.4610	0.5886	0.6229	0.069*
C5	0.3203 (3)	0.46854 (17)	0.72911 (13)	0.0578 (4)
H5	0.2166	0.5382	0.7410	0.069*
C6	0.3263 (3)	0.33451 (16)	0.78254 (12)	0.0496 (4)
H6	0.2261	0.3152	0.8299	0.060*
C7	0.4854 (2)	0.08246 (15)	0.82520 (11)	0.0427 (3)
H7	0.3652	0.0799	0.8692	0.051*
C8	0.7273 (3)	0.07618 (17)	0.89975 (11)	0.0488 (4)
H8A	0.7261	−0.0220	0.9319	0.059*
H8B	0.8482	0.0813	0.8572	0.059*
C9	0.7936 (3)	0.20195 (16)	0.98715 (11)	0.0463 (3)
C10	1.1203 (4)	0.3609 (2)	1.09571 (16)	0.0793 (6)
H10A	1.0243	0.4439	1.0931	0.119*
H10B	1.2801	0.4007	1.0937	0.119*
H10C	1.1199	0.3104	1.1609	0.119*
C11	0.4293 (2)	−0.06163 (16)	0.74809 (12)	0.0487 (4)
H11A	0.5381	−0.0554	0.6996	0.058*
H11B	0.4573	−0.1507	0.7892	0.058*
C12	0.1809 (3)	−0.08498 (16)	0.68321 (12)	0.0474 (3)
C13	−0.0740 (4)	−0.2120 (3)	0.52859 (17)	0.0895 (6)
H13A	−0.1606	−0.2865	0.5633	0.134*
H13B	−0.0641	−0.2549	0.4593	0.134*
H13C	−0.1546	−0.1218	0.5202	0.134*
O1	1.02509 (18)	0.25234 (13)	1.00486 (9)	0.0591 (3)
O2	0.6623 (2)	0.25035 (15)	1.03815 (10)	0.0713 (4)
O3	0.1625 (2)	−0.17144 (14)	0.59333 (9)	0.0671 (3)
O4	0.0144 (2)	−0.03577 (17)	0.70777 (11)	0.0850 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0367 (7)	0.0427 (7)	0.0383 (7)	0.0014 (6)	0.0042 (5)	−0.0019 (6)
C2	0.0524 (9)	0.0602 (9)	0.0589 (9)	0.0142 (7)	0.0209 (7)	0.0101 (7)
C3	0.0660 (10)	0.0697 (11)	0.0601 (10)	0.0054 (9)	0.0240 (8)	0.0175 (8)
C4	0.0665 (10)	0.0476 (8)	0.0548 (9)	0.0017 (7)	0.0033 (8)	0.0099 (7)
C5	0.0613 (10)	0.0451 (8)	0.0673 (10)	0.0143 (7)	0.0109 (8)	0.0005 (7)
C6	0.0500 (8)	0.0464 (8)	0.0549 (9)	0.0067 (6)	0.0167 (7)	0.0011 (7)
C7	0.0403 (7)	0.0432 (7)	0.0441 (7)	0.0044 (6)	0.0085 (6)	0.0010 (6)
C8	0.0484 (8)	0.0486 (8)	0.0477 (8)	0.0108 (6)	0.0041 (6)	0.0026 (6)
C9	0.0467 (8)	0.0503 (8)	0.0414 (7)	0.0086 (6)	0.0061 (6)	0.0080 (6)
C10	0.0702 (12)	0.0790 (12)	0.0741 (12)	−0.0042 (10)	−0.0060 (10)	−0.0174 (10)
C11	0.0474 (8)	0.0435 (8)	0.0542 (8)	0.0066 (6)	0.0083 (7)	−0.0007 (6)
C12	0.0487 (8)	0.0417 (7)	0.0511 (8)	0.0011 (6)	0.0120 (7)	−0.0007 (6)
C13	0.0772 (13)	0.0980 (15)	0.0754 (13)	−0.0134 (11)	−0.0073 (10)	−0.0194 (11)
O1	0.0474 (6)	0.0657 (7)	0.0592 (7)	0.0014 (5)	0.0048 (5)	−0.0079 (5)
O2	0.0604 (7)	0.0865 (9)	0.0668 (7)	0.0044 (6)	0.0206 (6)	−0.0181 (6)
O3	0.0603 (7)	0.0713 (7)	0.0625 (7)	0.0036 (6)	0.0047 (6)	−0.0208 (6)
O4	0.0469 (7)	0.1122 (11)	0.0901 (9)	0.0096 (7)	0.0109 (6)	−0.0360 (8)

Geometric parameters (Å, º) top

C1—C6	1.3803 (18)	C8—H8B	0.9700
C1—C2	1.3855 (19)	C9—O2	1.1962 (17)
C1—C7	1.5166 (18)	C9—O1	1.3357 (18)
C2—C3	1.383 (2)	C10—O1	1.441 (2)
C2—H2	0.9300	C10—H10A	0.9600
C3—C4	1.364 (2)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
C4—C5	1.366 (2)	C11—C12	1.492 (2)
C4—H4	0.9300	C11—H11A	0.9700
C5—C6	1.385 (2)	C11—H11B	0.9700
C5—H5	0.9300	C12—O4	1.1908 (18)
C6—H6	0.9300	C12—O3	1.3244 (18)
C7—C11	1.5283 (19)	C13—O3	1.444 (2)
C7—C8	1.5299 (19)	C13—H13A	0.9600
C7—H7	0.9800	C13—H13B	0.9600
C8—C9	1.492 (2)	C13—H13C	0.9600
C8—H8A	0.9700

C6—C1—C2	117.79 (13)	C7—C8—H8B	108.7
C6—C1—C7	121.06 (12)	H8A—C8—H8B	107.6
C2—C1—C7	121.15 (12)	O2—C9—O1	123.14 (14)
C3—C2—C1	120.70 (14)	O2—C9—C8	125.79 (14)
C3—C2—H2	119.7	O1—C9—C8	111.03 (12)
C1—C2—H2	119.7	O1—C10—H10A	109.5
C4—C3—C2	120.75 (15)	O1—C10—H10B	109.5
C4—C3—H3	119.6	H10A—C10—H10B	109.5
C2—C3—H3	119.6	O1—C10—H10C	109.5
C3—C4—C5	119.34 (14)	H10A—C10—H10C	109.5
C3—C4—H4	120.3	H10B—C10—H10C	109.5
C5—C4—H4	120.3	C12—C11—C7	114.15 (11)
C4—C5—C6	120.37 (14)	C12—C11—H11A	108.7
C4—C5—H5	119.8	C7—C11—H11A	108.7
C6—C5—H5	119.8	C12—C11—H11B	108.7
C1—C6—C5	121.05 (14)	C7—C11—H11B	108.7
C1—C6—H6	119.5	H11A—C11—H11B	107.6
C5—C6—H6	119.5	O4—C12—O3	122.43 (15)
C1—C7—C11	112.33 (11)	O4—C12—C11	125.58 (14)
C1—C7—C8	111.83 (11)	O3—C12—C11	111.98 (12)
C11—C7—C8	108.24 (11)	O3—C13—H13A	109.5
C1—C7—H7	108.1	O3—C13—H13B	109.5
C11—C7—H7	108.1	H13A—C13—H13B	109.5
C8—C7—H7	108.1	O3—C13—H13C	109.5
C9—C8—C7	114.04 (11)	H13A—C13—H13C	109.5
C9—C8—H8A	108.7	H13B—C13—H13C	109.5
C7—C8—H8A	108.7	C9—O1—C10	117.15 (13)
C9—C8—H8B	108.7	C12—O3—C13	116.62 (14)

C6—C1—C2—C3	0.0 (2)	C1—C7—C8—C9	61.88 (15)
C7—C1—C2—C3	−179.85 (14)	C11—C7—C8—C9	−173.87 (12)
C1—C2—C3—C4	−0.3 (3)	C7—C8—C9—O2	40.5 (2)
C2—C3—C4—C5	0.5 (3)	C7—C8—C9—O1	−141.58 (13)
C3—C4—C5—C6	−0.4 (3)	C1—C7—C11—C12	−66.14 (15)
C2—C1—C6—C5	0.1 (2)	C8—C7—C11—C12	169.91 (12)
C7—C1—C6—C5	179.92 (14)	C7—C11—C12—O4	−24.7 (2)
C4—C5—C6—C1	0.1 (2)	C7—C11—C12—O3	156.52 (12)
C6—C1—C7—C11	121.25 (14)	O2—C9—O1—C10	5.2 (2)
C2—C1—C7—C11	−58.94 (17)	C8—C9—O1—C10	−172.73 (14)
C6—C1—C7—C8	−116.81 (14)	O4—C12—O3—C13	−3.8 (2)
C2—C1—C7—C8	62.99 (17)	C11—C12—O3—C13	175.03 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O4ⁱ	0.97	2.53	3.3987 (19)	149

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆O₄
M_r	236.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.7944 (2), 8.7668 (3), 12.7591 (4)
α, β, γ (°)	92.609 (2), 101.979 (2), 96.140 (2)
V (Å³)	628.86 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.26 × 0.13

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8883, 2207, 1839
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.116, 1.07
No. of reflections	2207
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O4ⁱ	0.97	2.53	3.3987 (19)	148.7

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was financially supported by the Natural Science Foundation of Shaanxi Provinces of China (SJ08B11).

References

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Yang, J.-H., Zhang, J.-M., Chen, Y.-X., Diao, J.-Z. & Peng, Z. (2008). Acta Cryst. E64, o1100. Web of Science CSD CrossRef IUCr Journals Google Scholar