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X-ray powder diffraction data for N,N-dimethyl-1H-benzo[d]imidazol-2-amine, C9H11N3

Published online by Cambridge University Press:  22 April 2021

Xia Lin ,
Dan-dan Chen ,
Xiao-hui Lin ,
An-tao Liu ,
Bao Zong  and
Lian-jia Zou Open the ORCID record for Lian-jia Zou [Opens in a new window]
Xia Lin
Affiliation:
Guangxi Medical College, Nanning 530023, China Medical College, Guangxi University, Nanning 530004, China College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China
Dan-dan Chen
Affiliation:
Guangxi Medical College, Nanning 530023, China
Xiao-hui Lin
Affiliation:
Guangxi Medical College, Nanning 530023, China
An-tao Liu
Affiliation:
Guangxi Medical College, Nanning 530023, China
Bao Zong
Affiliation:
Guangxi Medical College, Nanning 530023, China
Lian-jia Zou*
Affiliation:
Guangxi Medical College, Nanning 530023, China
*
a)Author to whom correspondence should be addressed. Electronic mail: lianjiazou_gxmc@sina.com

Abstract

X-ray powder diffraction data, unit-cell parameters, and space group for N,N-dimethyl-1H-benzo[d]imidazol-2-amine, C9H11N3, are reported [a = 11.379(3) Å, b = 10.227(5) Å, c = 7.151(1) Å, α = 90°, β = 90°, γ = 90°, unit-cell volume V = 832.318 Å3, Z = 4, ρcal = 1.286 g cm−3, and space group P21212]. All measured lines were indexed and were consistent with the P21212 space group. No detectable impurities were observed.

Keywords

X-ray powder diffractionN,N-dimethyl-1h-benzo[d]imidazol-2-amineCryptotaenia japonica extractive

Information

Type
Data Report
Information
Powder Diffraction , Volume 36 , Issue 2 , June 2021 , pp. 140 - 142
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Copyright
Copyright © The Author(s), 2021. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

I. INTRODUCTION

N,N-Dimethyl-1H-benzo[d]imidazol-2-amine (Figure 1) is an extract of herbal medicine Cryptotaenia japonica, which was isolated for the first time by Liu et al. (Reference Liu, Zhang and Liang2018). It is one of the special components in this plant, which has not been found in other plants. It is recorded in the pharmacopeia of traditional Chinese medicine that C. japonica has many medicinal values, such as anti-inflammatory, detoxification, promoting blood circulation, reducing swelling, treating lung disease, gonorrhea, toothache, anti-infection, and anti-virus (Yang and Xia, Reference Yang and Xia2010). For example, crude flavonoids extracted from this plant have antioxidant activity in vitro (Lu et al., Reference Lu, Xu, Yang, Fu, Luo and Li2015). Its methanol extract has protective effects against lipopolysaccharide-induced inflammation in vitro and in vivo (Kang et al., Reference Kang, Bang, Lee, Lew, Eom, Li and Choi2012). Kaempferol-7-O-β-D-glucuronide and tilianin, isolated from this plant, show anti-melanogenic potential (Seong et al., Reference Seong, Lee, Poudel, Oh and Lee2016). Hence, it can be speculated that the title compound may play a key role in the pharmacological activity of the designated plant. At present, the detailed X-ray powder diffraction (XRD) data for it have not been reported.

Figure 1.

Chemical structure of N,N-dimethyl-1H-benzo[d]imidazol-2-amine.

II. EXPERIMENTAL

A. Sample preparation

The sample (Figure 1) was extracted (60% ethanol, heating reflux), isolated, and purified (ethyl acetate extracted, then separated by silica gel column, hydroxypropyl dextran gel column, octadecyl silane bonded silica gel column) from C. japonica. The natural sample was analyzed by high-performance liquid chromatography (HPLC). As seen in Figure 2, the chromatogram shows that its purity is satisfactory. The melting point and measured density of it are 325.17 °C (Figure 3) and 1.271 g cm−3, respectively. The crystallization of the title compound at room temperature was successful using chloroform-ethyl acetate (10:1, v/v) as a solvent. Then, the crystals were dried, smashed, and mounted on a flat zero background plate.

Figure 2.

HPLC pattern of N,N-dimethyl-1H-benzo[d]imidazol-2-amine.

Figure 3.

DSC pattern of N,N-dimethyl-1H-benzo[d]imidazol-2-amine.

B. Diffraction data collection and reduction

XRD measurement was performed at room temperature using a Bruker D8 Advance diffractometer (Bruker, AXS, Germany) with a LynxEye array detector and CuKα radiation (generator setting: 40 kV and 40 mA). The diffraction data were collected over the angular range from 5 to 50° 2θ with a step size of 0.020464° 2θ (time of diffraction measurement ~10 min) (Figure 4).

Figure 4.

XRD pattern of N,N-dimethyl-1H-benzo[d]imidazol-2-amine using CuKα radiation.

The software package Material Studio 8.0 (Accelrys Co., Ltd., CA, USA) was used to process the data in the multi-function computing platform (Guangxi University, Nanning). The XRD pattern was processed by subtracting the background, smoothing, and stripping off the Kα 2 component. Automatic indexing results were obtained by the DICVOL91 method (Boultif and Louër, Reference Boultif and Louër1991). The following figures of merit were achieved: F 20 = 19.9 (0.0157, 46) (Smith and Snyder, Reference Smith and Snyder1979) and M 20 = 15.6 (de Wolff, Reference de Wolff1968). The indexing results were then refined using Pawley (Reference Pawley1981), which involves assigning the Miller indices (h, k, l) to each observed peak in the experimental powder XRD pattern.

III. RESULTS

Pawley refinement results confirmed that the title compound is orthorhombic with space group P21212 and unit-cell parameters: a = 11.379(3) Å, b = 10.227(5) Å, c = 7.151(1) Å, α = 90°, β = 90°, γ = 90°, unit-cell volume V = 832.318 Å3, Z = 4, ρ cal = 1.286 g cm−3. The values of 2θ obs, d obs, I obs, h, k, l, 2θ cal, d cal, and Δ2θ are listed in Table I.

TABLE I.

Indexed X-ray powder diffraction data for N,N-dimethyl-1H-benzo[d]imidazol-2-amine.

The d-values were calculated using CuKα 1 radiation (λ = 1.5405981 Å).

IV. DEPOSITED DATA

CIF and or RAW data files were deposited with ICDD. You may request this data from ICDD at .

ACKNOWLEDGEMENTS

This work was supported by the 2017 basic ability improvement project for young and middle-aged teachers in colleges and universities in Guangxi (Grant No. 2017KY1226).

References

Boultif, A. and Louër, D. (1991). “Indexing of powder diffraction patterns for low-symmetry lattices by the successive dichotomy method,” J. Appl. Crystallogr. 24, 987–993.CrossRefGoogle Scholar
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Figure 0

Figure 1. Chemical structure of N,N-dimethyl-1H-benzo[d]imidazol-2-amine.

Figure 1

Figure 2. HPLC pattern of N,N-dimethyl-1H-benzo[d]imidazol-2-amine.

Figure 2

Figure 3. DSC pattern of N,N-dimethyl-1H-benzo[d]imidazol-2-amine.

Figure 3

Figure 4. XRD pattern of N,N-dimethyl-1H-benzo[d]imidazol-2-amine using CuKα radiation.

Figure 4

TABLE I. Indexed X-ray powder diffraction data for N,N-dimethyl-1H-benzo[d]imidazol-2-amine.