Home The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
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The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4

  • Wan-li Liu , Hong Sui , Gai-mei She EMAIL logo , Hai-Yuan Quan and Dong-Mei She
Published/Copyright: September 5, 2018

Abstract

C27H33Cl3N4O4, monoclinic, P21/n (no. 14), a = 7.1343(4) Å, b = 22.4930(10) Å, c = 9.7835(4) Å, β = 106.876(5), V = 1502.37(13) Å3, Z = 2, Rgt(F) = 0.0605, wRref(F2) = 0.1517, T = 179.99(10) K

CCDC no.: 1862142

Table 1:

Crystal collection and handling.

Crystal:Block, colorless
Size:0.4 × 0.2 × 0.15 mm
Wavelength:Mo Kα radiation (λ = 0.71073 Å)
μ:0.343 mm−1
Diffractometer, scan mode:XtaLAB AFC12, Φ-scans
θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:9882, 3449, 0.0237
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 2471
N(param)refined:199
Programs:CrysAlisPRO [1], OLEX2 [2], SHELX [3]

The title molecule of 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 2:

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

AtomxyzUiso*/Ueq
Cl1a0.7380(6)0.9834(2)1.0377(7)0.2075(17)
Cl2a0.4369(12)1.03526(19)1.1120(7)0.228(2)
Cl3a0.3640(10)0.9696(2)0.8713(4)0.226(2)
C14a0.5216(13)1.0160(3)0.9642(9)0.124(3)
H14a0.535(3)1.0531(7)0.921(2)0.149
O11.0818(2)0.82421(7)0.84418(15)0.0585(4)
O21.1315(2)0.79755(7)0.62672(14)0.0538(4)
N10.8019(2)0.73629(8)0.56148(15)0.0407(4)
H1A0.836(3)0.7523(9)0.486(2)0.049
N20.8188(2)0.71581(7)0.78543(15)0.0377(4)
C11.0890(3)0.77795(10)0.74974(19)0.0450(5)
H11.19250.75030.79960.054
C20.9330(4)0.86695(12)0.7872(3)0.0761(8)
H2A0.95690.88590.70600.114
H2B0.93380.89630.85870.114
H2C0.80780.84760.75850.114
C31.3273(4)0.81779(13)0.6519(3)0.0639(7)
H3A1.35310.82480.56230.096
H3B1.41610.78820.70480.096
H3C1.34490.85410.70580.096
C40.9023(3)0.74391(9)0.70041(17)0.0374(4)
C50.6455(3)0.70124(9)0.55780(19)0.0446(5)
H50.55000.68840.47660.054
C60.6554(3)0.68843(8)0.69643(18)0.0370(4)
C70.5243(3)0.65141(9)0.75170(19)0.0392(4)
C80.5963(3)0.61962(9)0.8787(2)0.0428(5)
H80.72820.62240.92960.051
C90.4738(3)0.58414(10)0.9297(2)0.0492(5)
H90.52510.56301.01400.059
C100.2757(3)0.57921(10)0.8581(2)0.0514(5)
C110.2040(3)0.61126(11)0.7325(2)0.0559(6)
H110.07150.60900.68310.067
C120.3258(3)0.64663(10)0.6794(2)0.0506(5)
H120.27430.66740.59450.061
C130.1406(4)0.54248(13)0.9168(3)0.0739(8)
H13A0.05460.51980.84100.111
H13B0.06440.56820.95820.111
H13C0.21640.51600.98870.111
  1. a = 0.5

Source of material

The title molecule was synthesized according to a method reported previously [4]. By cyclocondensation of acylmethylamine ZCOCH2NH2 mineral acid salt (Z = alkyl) with acetimidate ester AOC(:NH)CH(OR)2 (A = alkyl). Thus, 0.77 g 28% NaOMe in MeOH was added to 12 mL MeOH, followed by adding dropwise 2.58 g (EtO)2CHCN, and the mixt. was allowed to react at room temp. for 1 h to give a solution of (EtO)2CHC(:NH)OMe in MeOH. To the latter solution was added portionwise 1.85 g 4-methylphenacylamine hydrochloride and then adding dropwise 1.93 g 28% NaOMe in MeOH. The mixture was allowed to react at room temp. for 1 h and then under refluxing for 2 h. Crystals of the title compound was obtained in a mixed solvent of petroleum ether and chloroform (v/v = 3:1). After stirring for 10 min at room temperature, the mixture was filtered and the filtrate was allowed to stand at room temperature for a week [5]. The solvent partially evaporated and colourless block crystals were obtained.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms. Data reduction and empirical absorption correction were performed using the CrysAlisPRO program [1]. Using Olex2 [2], the crystal structure was solved by Direct Methods and refined with the SHELX program system [3].

Comment

The title compound, 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole and other imidazole derivatives are important agricultural intermediates [6]. It is important to determine the structure of synthetic compounds by X-ray single crystal diffraction before the study of the biological activity. The molecule is mainly composed of a substituted (1H)-imidazole ring and a methylphenyl moiety. The asymmetric unit of the title compound contains one title molecule and one half occupied chloroform molecule. In the figure the solvent molecules have been omitted for clarity [7].

Acknowledgements

This work was supported by The National Key Research and Development Program of China [grant number 2016YFD0200201] and The National Key Technology R&D Program of China [grant number 2015BAK45B01]. The author thanks the referees and the members of the editorial office for their very helpful critical comments on the first draft.

References

CrysAlisPRO 1.171.39.29a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.Search in Google Scholar

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

Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

Ooshima, T.: Method for producing imidazole-1-carboxaldehyde dialkyl acetal derivatives. Ishihara Sangyo Kaisha, Japan (1995); JP 07126254 A.Search in Google Scholar

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Received: 2018-06-26
Accepted: 2018-08-15
Published Online: 2018-09-05
Published in Print: 2018-11-27

©2018 Wan-li Liu 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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