Dimethyl 3-phenyl-penta-nedioate.

In the title compound, C(13)H(16)O(4), the terminal carboxyl-ate groups are twisted to each other at a dihedral angle of 23.80 (9)°. Weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into supra-molecular 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 = 236.26

Triclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.116

S = 1.07

2207 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041954/xu5052Isup2.hkl

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

C13H16O4	Z = 2
Mr = 236.26	F(000) = 252
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0636P)2 + 0.0827P] where P = (Fo2 + 2Fc2)/3
2207 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.14 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
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)

	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)

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)

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

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) .