Home Crystal structure of (E)-2,4-diiodo-6-(4-methyl-2-nitrostyryl)phenol, C14H10I2N2O3
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Crystal structure of (E)-2,4-diiodo-6-(4-methyl-2-nitrostyryl)phenol, C14H10I2N2O3

  • Yong Hong EMAIL logo , Wei Liu and Heping Yan
Published/Copyright: April 20, 2018

Abstract

C14H10I2N2O3, monoclinic, P21/c (no. 14), a = 13.5219(8) Å, b = 7.2772(4) Å, c = 15.2709(8) Å, β = 96.1761(18)°, V = 1493.96(14) Å3, Z = 4, Rgt(F) = 0.0716, wRref(F2) = 0.1888, T = 293(2) K.

CCDC no.: 1813249

The 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:

Data collection and handling.

Crystal:Colorless block
Size:0.32 × 0.24 × 0.17 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:4.22 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:22474, 3432, 0.043
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2495
N(param)refined:192
Programs:Bruker programs [1], SHELX [2], OLEX2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
I10.07267(4)0.62072(7)0.28165(3)0.0449(2)
I20.16429(4)0.36809(8)−0.07512(3)0.0503(2)
O30.3003(4)0.5426(8)0.3190(3)0.0466(12)
H30.3608880.5344750.3299950.070*
N20.4789(5)0.4446(9)0.2906(4)0.0414(13)
C110.2122(6)0.4164(10)0.0580(5)0.0419(16)
O10.5433(4)0.3181(8)0.5405(4)0.0493(13)
O20.4665(4)0.1969(9)0.4230(4)0.0513(13)
N10.5333(5)0.2897(9)0.4610(4)0.0437(14)
C130.1737(6)0.5160(10)0.2001(5)0.0387(15)
C140.2741(6)0.4982(9)0.2340(5)0.0401(15)
C120.1421(6)0.4741(10)0.1132(5)0.0428(16)
H120.0753120.4840800.0918660.051*
C100.3117(6)0.3965(10)0.0883(5)0.0421(16)
H100.3574260.3564860.0510750.050*
C60.6070(6)0.3670(10)0.4093(5)0.0398(15)
C50.5813(6)0.4254(10)0.3222(5)0.0414(16)
C20.7810(6)0.4291(10)0.3985(5)0.0421(16)
C80.4478(6)0.4108(10)0.2110(5)0.0424(16)
H80.4918130.3679630.1728450.051*
C90.3423(6)0.4392(10)0.1785(5)0.0395(15)
C70.7063(6)0.3712(10)0.4469(5)0.0426(16)
H70.7219910.3345310.5050820.051*
C40.6571(6)0.4867(10)0.2748(5)0.0422(16)
H40.6417250.5298940.2176140.051*
C30.7549(6)0.4842(11)0.3118(5)0.0469(17)
H3A0.8046800.5201440.2778190.056*
C10.8879(6)0.4305(12)0.4390(6)0.0492(18)
H1A0.9087080.5548680.4513330.074*
H1B0.9293850.3764070.3987600.074*
H1C0.8937150.3611500.4928280.074*

Source of material

4-methyl-2-nitroaniline (1 mmol, 0.152 g) and 3,5-diiodosalicylaldehyde (1 mmol, 0.373 g) were added to the solution of ethanol (10 mL), then the mixture was refluxed 4 hrs. After filtering the residue was dissolved in dichloromethane and the solution was evaporated slowly at room temperature to obtain colorless prismatic crystals suitable for X-ray structure determination.

Experimental details

The H atoms were positioned geometrically with d(C—H) = 0.93–0.98 Å and refined as riding with Uiso(H) = 1.2 Ueq(carrier) or 1.5 Ueq(methyl). Solving, refining and finishing of the crystal structure were finished by OLEX2 [2] and SHELX [3] program systems. The data completeness is 1.00 up to the diffraction angle of 55.01°.

Discussion

Schiff bases of salicylaldehyde with amines (anils) comprise a chemical system undergoing hydrogen-atom tautomerism between enol and keto forms and show the phenomena of solid state photochromism and thermochromism [4]. Similar to the crystal structure of the related Schiff base [5, 6] , the titled compound with electron-withdrawing iodosubstituents (cf. the figure) clearly shows the enol form. The molecule displays an E-configuration at the central C7=N17 bond. The dihedral angle between the two substituted phenyl moieties (C1—C2—C3—C4—C5—C6 and C8—C9—C10—C11—C12—C13) is 39.09°. There is an intramolecular O—H⋯N hydrogen bond molecular structure of the title compound. All bond lengths and angles are in the expected ranges.

Acknowledgements

This work was financially supported by National Natural Science Foundation of China (Grant No. 21461007) and Applied Basic Research Project in Yunnan Province (Grant No. 2013FZ121), Open Fund of Master Construction Discipline in Yunnan Province (Grant No. HXB1401).

References

Bruker. APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, WI, USA (2009).Search in Google Scholar

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H.: OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 42 (2009) 339–341.10.1107/S0021889808042726Search in Google Scholar

Hadjoudis, E.; Chatziefthimiou, S. D.; Mavridis, I. M.: Anils: photochromism by H-transfer. Curr. Org. Chem. 13 (2009) 269–286.10.2174/138527209787314797Search in Google Scholar

Hong, Y.; Huang, D.; Liu, W.: Crystal structure of N-(3-hydroxy-phenyl)-5-chloro-salicylideneimine. Z. Kristallogr. NCS 231 (2016) 231–232.10.1515/ncrs-2015-0100Search in Google Scholar

Hong, Y., Gou, G.; Liu, W.; Yan, H.: Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino)methyl)phenol. Z. Kristallogr. NCS 232 (2017) 365–366.10.1515/ncrs-2016-0269Search in Google Scholar

Received: 2018-01-20
Accepted: 2018-04-04
Published Online: 2018-04-20
Published in Print: 2018-07-26

©2018 Yong Hong 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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