Home Crystal structure of N1,N2-bis(2-fluorobenzyl)benzene-1,2-diamine,C20H18F2N2
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Crystal structure of N1,N2-bis(2-fluorobenzyl)benzene-1,2-diamine,C20H18F2N2

  • Zhi Wei Ning , Lin Ling Gan , Shu Jing Zhou , Jie Tian , Yu Hui Du and Hui Zhen Zhang
Published/Copyright: April 9, 2021

Abstract

C20H18F2N2, monoclinic, P21/c (no. 14), a = 12.4233(11) Å, b = 7.3805(7) Å, c = 18.9531(16) Å, β = 104.109(3)°, V = 104.109(3) Å3, Z = 4, Rgt(F) = 0.0464, wRref(F2) = 0.1201, T = 296(2) K.

CCDC no.: 2074208

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless prism
Size:0.42 × 0.38 × 0.35 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:SMART, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:8005, 2957, 0.104
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1455
N(param)refined:236
Programs:Bruker [1], SHELX [2], [3], Olex2 [4]
Table 2:

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

AtomxyzUiso*/Ueq
C10.1777 (3)0.4570 (5)0.55252 (15)0.0748 (8)
H1a0.14860.54230.57880.090*
C20.1201 (3)0.2998 (5)0.53252 (16)0.0874 (10)
H20.05270.28060.54450.105*
C30.1624 (3)0.1705 (5)0.49465 (15)0.0862 (10)
H30.12440.06240.48130.103*
C40.2623 (3)0.2024 (4)0.47644 (14)0.0792 (9)
H40.29120.11730.44990.095*
C50.3174 (3)0.3599 (5)0.49794 (14)0.0701 (8)
H5b0.38550.37800.48690.084*
C60.2772 (2)0.4947 (4)0.53542 (12)0.0591 (7)
C70.3394 (2)0.6679 (4)0.55588 (12)0.0676 (8)
H7A0.37160.70630.51660.081*
H7B0.28860.76160.56340.081*
C80.5056 (2)0.7805 (4)0.64599 (12)0.0508 (6)
C90.4969 (2)0.9535 (4)0.61579 (13)0.0659 (8)
H90.43650.98260.57780.079*
C100.5774 (3)1.0823 (4)0.64200 (17)0.0771 (9)
H100.57091.19750.62150.093*
C110.6665 (3)1.0414 (4)0.69791 (18)0.0805 (9)
H110.72051.12870.71520.097*
C120.6766 (2)0.8709 (4)0.72870 (14)0.0660 (7)
H120.73750.84450.76670.079*
C130.5976 (2)0.7386 (3)0.70390 (12)0.0510 (6)
C140.7040 (2)0.5046 (3)0.78625 (12)0.0603 (7)
H14A0.68740.39220.80790.072*
H14B0.72010.59550.82440.072*
C150.8058 (2)0.4773 (3)0.75771 (11)0.0489 (6)
C160.9073 (2)0.4380 (4)0.80387 (12)0.0613 (7)
C171.0027 (2)0.4067 (4)0.78206 (15)0.0778 (9)
H171.06870.38030.81590.093*
C180.9990 (3)0.4149 (4)0.70898 (16)0.0838 (9)
H181.06270.39540.69250.101*
C190.9000 (3)0.4524 (4)0.66086 (14)0.0755 (9)
H190.89670.45660.61130.091*
C200.8048 (2)0.4841 (3)0.68435 (13)0.0609 (7)
H200.73890.51040.65040.073*
F1a0.4115 (3)0.3927 (5)0.48346 (14)0.0980 (14)
F1Ab0.1450 (4)0.5726 (6)0.5906 (3)0.113 (2)
F20.91046 (14)0.4293 (2)0.87692 (7)0.0986 (6)
N10.42681 (18)0.6445 (4)0.62191 (10)0.0590 (6)
H1A0.454 (2)0.539 (4)0.6348 (14)0.079 (10)*
N20.6066 (2)0.5608 (3)0.73116 (11)0.0560 (6)
H2A0.545 (3)0.527 (4)0.7344 (15)0.092 (11)*
  1. a Occupancy: 0.579(5), b Occupancy: 0.421(5).

Source of material

A mixture of o-phenylene diamine (0.541 g, 5 mmol), 1-bromopropane (0.615 g, 5 mmol) and potassium carbonate (0.828 g, 6 mmol) was stirred in ethanol at room temperature. After the reaction was completed (monitored by TLC, eluent, dichloromethane/petroleum ether, 1/1, v/v), the solvent was removed and the residue was extracted with dichloromethane (3 × 40 mL), dried over anhydrous sodium sulfate and purified by silica gel column chromatography (eluent, dichloromethane/petroleum ether, 1/1, v/v) to afford the white solid. Yield, 645 mg, 40%. The title compound was dissolved in dichloromethane, and the solvent was evaporated slowly at room temperature. After three days, colorless crystals were obtained.

Experimental details

Data reduction was carried out using SAINT+ and SADABS [1]. The structure was determined by intrinsic phasing routines in the SHELXT program [2] and refined by full-matrix least-squares methods in SHELXL [3] by using Olex 2 [4]. All of the hydrogen atoms were placed in the calculated positions.

Comment

Phenylamine derivatives are an important class of organic compounds, which have a wide range of applications in medicine and chemical industry [5], [6]. For instance, phenylamines are widely used as antimicrobial drugs, anti-inflammatory analgesics and antilipemic drugs in the field of medicine, and as insecticides and fungicides in the field of pesticides [7]. Additionally, phenylamines can also be used to synthesize some important medicinal intermediates and other chemicals with important application value in organic synthesis [8]. Although N1,N2-bis(2-fluorobenzyl)benzene-1,2-diamine is a known compound, its crystal structure has not been reported yet. Therefore, in consideration of the importance of this compound it was synthesized form commercial material, and also its crystal structure will be reported.

There is one molecule in the asymmetric unit (see the Figure). The bond lengths and angles in the title molecule are in normal ranges. In a word, the title compound was synthesized under mild conditions, which can be readily used as a key intermediate to develop new drugs, novel reagents and advanced materials.


Corresponding author: Hui Zhen Zhang, School of Pharmacy, Linyi University, Linyi, 276000, P. R. China, E-mail:

Award Identifier / Grant number: ZR2020QB167

Funding source: Key Research and Development project of Shandong Province

Award Identifier / Grant number: 2019GSF108216

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by Shandong Provincial Natural Science Foundation (No. ZR2020QB167) and Key Research and Development project of Shandong Province (No. 2019GSF108216).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2021-03-17
Accepted: 2021-03-30
Published Online: 2021-04-09
Published in Print: 2021-07-27

© 2021 Zhi Wei Ning et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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