(2RS,3SR)-Diethyl 2,3-bis­(1,3-benzodioxole-5-carbon­yl)succinate

In the centrosymmetric title compound, C₂₄H₂₂O₁₀, the two aromatic rings are parallel to each other. The crystal packing is stabilized mainly by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.177
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

1,4-Diketones are important intermediates for synthesis of some natural products consisting of cyclopentanone and a furan ring system (Memurry & Meiton, 1971; Ito et al., 1975, 1977). As part of a study of these compounds, we report here the crystal structure of (2RS,3SR)-diethyl 2,3-bis(1,3-benzodioxole-5-carbonyl)succinate, (I).

The asymmetric unit of (I) contains a half-molecule with the other half generated inversion symmetry (Fig. 1 and Table 1). The two aromatic rings in (I) are parallel to each other and the aromatic ring is effectively coplanar with the five-membered C1/O1/C2/C3/O2 ring, making a dihedral angle of 1.06°. The crystal packing (Fig. 2) is stabilized mainly by van der Waals forces.

S2. Experimental

The title compound was synthesized according to the literature procedure of Wu et al. (1997). Crystals of (I) suitable for data collection were obtained by slow evaporation of a methanol–ethyl acetate solution.

S3. Refinement

The methyl H atoms were constrained to an ideal geometry, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å for phenyl H atoms, 0.97 Å for methene H atoms and U_iso(H) = 1.2U_eq(C) for both.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures

	Fig. 1. View of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (a) −x, 2 − y, −z.]
	Fig. 2. The packing of (I).

(2RS,3SR)-Diethyl 2,3-bis(1,3-benzodioxole-5-carbonyl)succinate

Crystal data

C24H22O10	F(000) = 492
Mr = 470.42	Dx = 1.395 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 1024 reflections
a = 8.0043 (10) Å	θ = 2.8–19.5°
b = 9.5866 (13) Å	µ = 0.11 mm^−1
c = 14.6977 (19) Å	T = 292 K
β = 96.778 (2)°	Block, colorless
V = 1119.9 (3) Å^3	0.30 × 0.20 × 0.12 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	2189 independent reflections
Radiation source: fine-focus sealed tube	1236 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ϕ and ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
Tmin = 0.968, Tmax = 0.987	k = −11→11
5842 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.177	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0815P)^2 + 0.1299P] where P = (Fo^2 + 2Fc^2)/3
2189 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.24 e Å^−3
1 restraint	Δρmin = −0.14 e Å^−3

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
C1	0.4350 (5)	0.2948 (4)	0.0936 (3)	0.0935 (11)
H1A	0.5495	0.2728	0.0831	0.112*
H1B	0.3782	0.2086	0.1059	0.112*
C2	0.2835 (3)	0.4826 (3)	0.0473 (2)	0.0662 (8)
C3	0.3361 (4)	0.4973 (3)	0.1390 (2)	0.0698 (8)
C4	0.1847 (3)	0.5780 (3)	−0.00098 (18)	0.0648 (8)
H4	0.1501	0.5658	−0.0631	0.078*
C5	0.2908 (4)	0.6088 (4)	0.1869 (2)	0.0812 (9)
H5	0.3264	0.6184	0.2491	0.097*
C6	0.1364 (3)	0.6958 (3)	0.04577 (17)	0.0585 (7)
C7	0.1883 (4)	0.7093 (3)	0.13897 (18)	0.0704 (8)
H7	0.1543	0.7867	0.1702	0.084*
C8	0.0330 (3)	0.8016 (3)	−0.00753 (18)	0.0620 (7)
C9	−0.0066 (3)	0.9417 (3)	0.03436 (17)	0.0591 (7)
H9	0.0743	0.9589	0.0886	0.071*
C10	−0.1831 (4)	0.9389 (3)	0.0627 (2)	0.0701 (8)
C11	−0.3564 (5)	0.8434 (5)	0.1666 (3)	0.1238 (15)
H11A	−0.4434	0.8480	0.1149	0.149*
H11B	−0.3636	0.7530	0.1956	0.149*
C12	−0.3829 (7)	0.9534 (6)	0.2318 (3)	0.158 (2)
H12A	−0.2936	0.9515	0.2815	0.238*
H12B	−0.4885	0.9388	0.2552	0.238*
H12C	−0.3840	1.0423	0.2017	0.238*
O1	0.3495 (3)	0.3619 (2)	0.01556 (15)	0.0925 (7)
O2	0.4356 (3)	0.3873 (3)	0.16917 (16)	0.0960 (8)
O3	−0.0222 (3)	0.7800 (2)	−0.08714 (13)	0.0862 (7)
O4	−0.2990 (3)	0.9971 (3)	0.02267 (18)	0.1142 (10)
O5	−0.1912 (3)	0.8590 (3)	0.13468 (15)	0.0953 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.086 (2)	0.086 (3)	0.106 (3)	0.0094 (19)	−0.0031 (19)	0.011 (2)
C2	0.0602 (17)	0.071 (2)	0.0679 (18)	−0.0017 (15)	0.0086 (14)	0.0049 (15)
C3	0.0648 (19)	0.076 (2)	0.0664 (19)	−0.0078 (16)	−0.0013 (14)	0.0146 (16)
C4	0.0664 (18)	0.0736 (19)	0.0530 (15)	0.0000 (15)	0.0017 (13)	0.0017 (14)
C5	0.097 (2)	0.090 (2)	0.0539 (16)	−0.0044 (19)	−0.0029 (15)	0.0084 (17)
C6	0.0535 (15)	0.0689 (18)	0.0531 (15)	−0.0063 (13)	0.0066 (12)	0.0016 (14)
C7	0.0779 (19)	0.076 (2)	0.0573 (16)	−0.0030 (16)	0.0069 (14)	−0.0033 (15)
C8	0.0574 (16)	0.0712 (19)	0.0565 (16)	−0.0055 (14)	0.0033 (13)	0.0001 (14)
C9	0.0508 (16)	0.0694 (18)	0.0568 (15)	−0.0018 (13)	0.0050 (12)	−0.0002 (13)
C10	0.0593 (19)	0.078 (2)	0.074 (2)	−0.0008 (16)	0.0130 (15)	0.0010 (16)
C11	0.106 (3)	0.131 (3)	0.149 (4)	−0.002 (3)	0.079 (3)	0.018 (3)
C12	0.139 (4)	0.233 (6)	0.113 (3)	0.048 (4)	0.056 (3)	0.007 (4)
O1	0.1058 (17)	0.0834 (16)	0.0865 (15)	0.0224 (13)	0.0040 (13)	0.0021 (12)
O2	0.0981 (18)	0.0937 (17)	0.0901 (16)	0.0113 (13)	−0.0146 (13)	0.0252 (14)
O3	0.1045 (17)	0.0840 (15)	0.0641 (13)	0.0109 (12)	−0.0157 (11)	−0.0074 (11)
O4	0.0550 (14)	0.161 (3)	0.128 (2)	0.0083 (14)	0.0155 (13)	0.0489 (18)
O5	0.0859 (16)	0.1119 (18)	0.0966 (16)	0.0060 (13)	0.0462 (13)	0.0185 (14)

Geometric parameters (Å, º)

C1—O1	1.418 (4)	C7—H7	0.9300
C1—O2	1.421 (4)	C8—O3	1.219 (3)
C1—H1A	0.9700	C8—C9	1.526 (4)
C1—H1B	0.9700	C9—C9^i	1.518 (5)
C2—C4	1.354 (4)	C9—C10	1.520 (4)
C2—C3	1.371 (4)	C9—H9	0.9800
C2—O1	1.376 (3)	C10—O4	1.178 (3)
C3—C5	1.352 (4)	C10—O5	1.314 (4)
C3—O2	1.364 (4)	C11—C12	1.457 (5)
C4—C6	1.400 (4)	C11—O5	1.462 (4)
C4—H4	0.9300	C11—H11A	0.9700
C5—C7	1.400 (4)	C11—H11B	0.9700
C5—H5	0.9300	C12—H12A	0.9600
C6—C7	1.390 (3)	C12—H12B	0.9600
C6—C8	1.475 (4)	C12—H12C	0.9600
O1—C1—O2	107.8 (3)	C6—C8—C9	121.4 (2)
O1—C1—H1A	110.1	C9^i—C9—C10	109.6 (3)
O2—C1—H1A	110.1	C9^i—C9—C8	110.2 (3)
O1—C1—H1B	110.1	C10—C9—C8	109.8 (2)
O2—C1—H1B	110.1	C9^i—C9—H9	109.1
H1A—C1—H1B	108.5	C10—C9—H9	109.1
C4—C2—C3	122.5 (3)	C8—C9—H9	109.1
C4—C2—O1	127.9 (3)	O4—C10—O5	124.5 (3)
C3—C2—O1	109.5 (3)	O4—C10—C9	123.9 (3)
C5—C3—O2	128.6 (3)	O5—C10—C9	111.5 (3)
C5—C3—C2	121.5 (3)	C12—C11—O5	110.1 (4)
O2—C3—C2	109.8 (3)	C12—C11—H11A	109.6
C2—C4—C6	117.8 (2)	O5—C11—H11A	109.6
C2—C4—H4	121.1	C12—C11—H11B	109.6
C6—C4—H4	121.1	O5—C11—H11B	109.6
C3—C5—C7	117.3 (3)	H11A—C11—H11B	108.1
C3—C5—H5	121.3	C11—C12—H12A	109.5
C7—C5—H5	121.3	C11—C12—H12B	109.5
C7—C6—C4	119.4 (3)	H12A—C12—H12B	109.5
C7—C6—C8	122.9 (3)	C11—C12—H12C	109.5
C4—C6—C8	117.7 (2)	H12A—C12—H12C	109.5
C6—C7—C5	121.4 (3)	H12B—C12—H12C	109.5
C6—C7—H7	119.3	C2—O1—C1	106.0 (2)
C5—C7—H7	119.3	C3—O2—C1	106.3 (2)
O3—C8—C6	120.7 (3)	C10—O5—C11	116.8 (3)
O3—C8—C9	117.9 (2)
C4—C2—C3—C5	0.3 (4)	O3—C8—C9—C9^i	−40.7 (4)
O1—C2—C3—C5	179.0 (3)	C6—C8—C9—C9^i	138.6 (3)
C4—C2—C3—O2	−179.1 (3)	O3—C8—C9—C10	80.1 (3)
O1—C2—C3—O2	−0.4 (3)	C6—C8—C9—C10	−100.5 (3)
C3—C2—C4—C6	0.3 (4)	C9^i—C9—C10—O4	15.2 (5)
O1—C2—C4—C6	−178.1 (3)	C8—C9—C10—O4	−106.0 (4)
O2—C3—C5—C7	179.1 (3)	C9^i—C9—C10—O5	−167.5 (3)
C2—C3—C5—C7	−0.2 (5)	C8—C9—C10—O5	71.4 (3)
C2—C4—C6—C7	−1.1 (4)	C4—C2—O1—C1	−176.6 (3)
C2—C4—C6—C8	178.2 (2)	C3—C2—O1—C1	4.8 (3)
C4—C6—C7—C5	1.2 (4)	O2—C1—O1—C2	−7.3 (3)
C8—C6—C7—C5	−178.0 (3)	C5—C3—O2—C1	176.4 (3)
C3—C5—C7—C6	−0.6 (4)	C2—C3—O2—C1	−4.2 (3)
C7—C6—C8—O3	−173.4 (3)	O1—C1—O2—C3	7.1 (3)
C4—C6—C8—O3	7.3 (4)	O4—C10—O5—C11	−0.4 (5)
C7—C6—C8—C9	7.3 (4)	C9—C10—O5—C11	−177.7 (3)
C4—C6—C8—C9	−171.9 (2)	C12—C11—O5—C10	−88.5 (4)

Symmetry code: (i) −x, −y+2, −z.