Home Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
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Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7

  • Pavel V. Dorovatovskii , Nurlana D. Sadigova , Alejandro Cárdenas , Jonathan Cisterna and Iván Brito EMAIL logo
Published/Copyright: September 5, 2018

Abstract

C16H16O7, monoclinic, P21/n (no. 14), a = 12.830(3) Å, b = 8.1101(16) Å, c = 14.900(3) Å, β = 114.88(3)°, V = 1406.5(6) Å3, Z = 4, Rgt(F) = 0.0578, wRref(F2) = 0.1799, T = 100(2) K.

CCDC no.: 1861146

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Crystal collection and handling.

Crystal:Prism, colourless
Size:0.25 × 0.15 × 0.10 mm
Wavelength:synchrotron radiation (λ = 0.9699 Å)
μ:0.282 mm−1
Diffractometer, scan mode:synchrotron source
θmax, completeness:38.5°, >97%
N(hkl)measured, N(hkl)unique, Rint:13125, 3051, 0.0965
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 2293
N(param)refined:211
Programs:SHELX [1]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
C10.49596(18)0.7828(3)0.74001(16)0.0197(5)
H1A0.5576990.7352340.8000190.024
H1B0.5324170.8531530.7069700.024
O20.42176(12)0.88305(19)0.76850(11)0.0203(4)
C30.32894(19)0.9602(3)0.68657(17)0.0197(5)
H3A0.3610111.0338780.6515000.024
H3B0.2832761.0285600.7119620.024
C3A0.25123(18)0.8339(3)0.61457(15)0.0156(5)
C40.14311(18)0.8870(3)0.52386(16)0.0169(5)
H40.1280090.9917040.4923680.020
C50.07493(18)0.7548(3)0.49870(16)0.0175(5)
H50.0016910.7451590.4445190.021
C60.13864(17)0.6225(3)0.57473(15)0.0164(5)
H60.0884780.5358380.5838170.020
C6A0.24101(17)0.5543(3)0.55197(16)0.0157(5)
C70.32232(18)0.4288(3)0.63400(16)0.0180(5)
H70.2822450.3318570.6466280.022
C80.42161(18)0.3862(3)0.60684(17)0.0201(6)
H80.4326040.2861060.5788560.024
C90.48936(19)0.5183(3)0.63049(16)0.0197(5)
H90.5592810.5315070.6237340.024
C9A0.43087(18)0.6452(3)0.67109(16)0.0175(5)
C9B0.32100(17)0.7098(3)0.57792(15)0.0150(5)
O30.20060(12)0.72308(18)0.66095(10)0.0165(4)
O40.37938(12)0.53564(18)0.71785(11)0.0176(4)
C100.20355(18)0.4746(3)0.45164(17)0.0173(5)
O50.24502(13)0.4945(2)0.39265(12)0.0242(4)
O60.11832(12)0.36485(18)0.43728(11)0.0199(4)
C110.07643(19)0.2713(3)0.34575(16)0.0214(5)
H11A0.0489040.3473610.2894150.032
H11B0.0132310.1996670.3420400.032
H11C0.1388850.2037440.3440190.032
C120.35819(18)0.7856(3)0.50283(15)0.0158(5)
O70.45792(12)0.80065(19)0.51634(11)0.0226(4)
O80.27094(12)0.84531(19)0.42136(11)0.0207(4)
C130.3039(2)0.9123(3)0.34665(18)0.0280(6)
H13A0.2357750.9556330.2913680.042
H13B0.3386250.8251450.3226230.042
H13C0.3596801.0014890.3755530.042

Source of materials

Synthesis and their characterization by 1H and 13C-NMR, IR and HRMS methods are reported [21], [22].

Experimental details

H atoms were located in the difference Fourier map, but refined with fixed individual displacement parameters, using a riding model with C—H distances of 0.95–1.0 Å (for aromatic rings), and C—H distances 0.99, 0.98 Å for methylene and methyl groups, with U(H) values of 1.2Ueq(CAr and CH2) and 1.5Ueq(C) (for CH3).

Discussion

Weak interactions, such as hydrogen, halogen, chalcogen, pnicogen, tetrel and icosagen bonds were extensively used in the synthesis, catalysis, crystal engineering, drug delivery, etc. [2], [3], [4], [5], [6], [7], [8], [9], [10], [11], [12]. Among those, hydrogen bonding has turned out to be particularly suitable for design of organic and coordination compounds [13], [14], [15], [16], [17], [18], [19], [20].

The molecule comprises a fused hexacyclic system containing four five-membered rings in the usual envelope conformations with Cremer and Pople parameters [23] ranging from (Q(2) = 0.521(2)–0.581(2) Å; φ2 = 177.6(2)–181.6(3)°) and one six-membered ring adopting a chair conformation with Cremer and Pople parameters Q = 0.536(2) Å, θ = 4.1(2)°, φ = 14(4)°, respectively. In the crystal structure the molecules are linked by one strong C—O⋯H intermolecular hydrogen bonds which links molecules into centrosymmetric dimers with R22(10) graph-set notation [24]. The carboxylate groups are α-oriented. All distances and angles are normal.

Acknowledgements

X-ray crystallographic studies using synchrotron radiation were performed at the unique scientific facility Kurchatov Synchrotron Radiation Source supported by the Ministry of Education and Science of the Russian Federation (project code RFMEFI61917X0007). This work has also been partially supported by Universidad de Antofagasta, and Baku State University.

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Received: 2018-06-04
Accepted: 2018-08-09
Published Online: 2018-09-05
Published in Print: 2018-11-27

©2018 Pavel V. Dorovatovskii et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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