Home Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
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Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3

  • Yong Hong EMAIL logo , Gaozhang Gou , Wei Liu EMAIL logo and Heping Yan
Published/Copyright: March 23, 2017

Abstract

C14H10Br2N2O3, monoclinic, P21/c (no. 14), a = 10.4183(3) Å, b = 11.5741(3) Å, c = 14.0587(4) Å, β = 89.011(3)°, V = 1455.0(5) Å3, Z = 4, Rgt(F) = 0.0474, wRref(F2) = 0.1314, T = 293 K.

CCDC no.:: 1465500

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

Data collection and handling.

Crystal:Colourless prism
Size:0.28 × 0.24 × 0.21 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:71.8 cm−1
Diffractometer, scan mode:Bruker APEX-II, ω-scans
2θmax, completeness:136.4°, >97%
N(hkl)measured, N(hkl)unique, Rint:8305, 2601, 0.078
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2188
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
Br10.42470(3)−0.08083(7)0.22617(3)0.0662(2)
Br20.33951(4)0.12776(8)0.57074(3)0.0762(2)
C10.3315(2)−0.0009(5)0.3031(2)0.0437(7)
C20.3642(2)0.0345(5)0.3912(2)0.0482(8)
H20.43170.02440.41270.058*
C30.2948(3)0.0856(5)0.4480(2)0.0462(8)
C40.2312(2)0.0149(5)0.2679(2)0.0401(7)
C50.1950(3)0.1060(4)0.4165(2)0.0435(7)
H50.14960.14310.45510.052*
C60.1624(2)0.0706(4)0.3265(2)0.0378(7)
C70.0566(2)0.0962(4)0.2943(2)0.0387(7)
H70.01290.13640.33370.046*
C8−0.0794(2)0.0806(4)0.1820(2)0.0372(6)
C9−0.1097(2)0.1342(4)0.0934(2)0.0355(6)
C10−0.2087(2)0.1283(4)0.0550(2)0.0420(7)
H10−0.22560.1612−0.00470.050*
C11−0.2819(2)0.0731(5)0.1063(2)0.0433(7)
C12−0.2538(2)0.0242(5)0.1948(2)0.0469(8)
H12−0.3029−0.00990.23020.056*
C13−0.1542(2)0.0247(5)0.2324(2)0.0420(7)
H13−0.1375−0.01260.29150.050*
C14−0.3897(3)0.0651(6)0.0655(3)0.0591(10)
H14A−0.4132−0.05990.06650.089*
H14B−0.39500.10820.00480.089*
H14C−0.42960.14190.09940.089*
N10.02343(19)0.0638(4)0.21228(18)0.0376(6)
N2−0.03684(19)0.2107(4)0.03842(18)0.0416(6)
O10.20455(17)−0.0221(4)0.18116(16)0.0517(6)
H10.14540.00450.16770.077*
O20.03179(18)0.3047(4)0.07455(17)0.0596(7)
O3−0.0484(2)0.1801(4)−0.04213(17)0.0613(7)

Source of material

4-Methyl-2-nitroaniline (1 mmol, 0.152 g) and 3,5-dibromosalicylaldehyde (1 mmol, 0.180 g) were added to ethanol (10 mL). The mixture was refluxed for 4 h. The solution was evaporated slowly at room temperature to obtain colorless prismatic crystals of the title compound.

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).

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]. Compared with crystal structure of the related Schiff base [5], the title compound with electron-withdrawing bromo substituents (cf. the figure) clearly shows the enol form.

The molecule displays a E-configuration at the central C6=N2 bond. The dihedral angle between the two substituated phenyl moieties (C1—C2—C3—C4—C5—C6 and C8—C9—C10—C11—C12—C13) is 35.34°. 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.

Award Identifier / Grant number: 21461007

Award Identifier / Grant number: 21366011

Funding statement: This work was financially supported by National Natural Science Foundation of China (Grant No.21461007, 21366011) and Applied Basic Research Project in Yunnan Province (Grant No. 2013FZ121), Open Fund of Master Construction Discipline in Yunnan Province (Grant No. HXB1401).

References

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

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

3 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

4 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

5 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

Received: 2016-10-25
Accepted: 2017-3-10
Published Online: 2017-3-23
Published in Print: 2017-5-24

©2017 Yong Hong et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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