Home Crystal structure of (E)-amino(2-(4-(dimethylamino)benzylidene)hydrazineyl)methaniminium nitrate, C10H16N6O3
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Crystal structure of (E)-amino(2-(4-(dimethylamino)benzylidene)hydrazineyl)methaniminium nitrate, C10H16N6O3

  • Xiao-Jing Liu ORCID logo , E. Liu , Ze-Sen Jin ORCID logo , Zhuang-Yu Li ORCID logo , Fang-Fang Jian EMAIL logo and Tongling Liang
Published/Copyright: April 26, 2021

Abstract

C10H16N6O3, monoclinic, P21/c (no. 14), a = 7.2312(1) Å, b = 17.7721(3) Å, c = 11.0146(2) Å, β = 104.557°, V = 1370.08(4) Å3, Z = 4, Rgt (F) = 0.0532, wRref (F2) = 0.1537, T = 170.0 K.

CCDC no.: 2076114

The asymmetric unit of the title crystal 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 block
Size:0.32 × 0.21 × 0.18 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.84 mm−1
Diffractometer, scan mode:XtaLAB Synergy R, ω
θmax, completeness:75.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:9426, 2698, 0.022
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2450
N(param)refined:174
Programs:CrysAlisPRO [1], SHELX [2], [3], Olex2 [4]
Table 2:

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

AtomxyzUiso*/Ueq
O1−0.05663 (16)0.82525 (8)0.17718 (11)0.0485 (3)
O20.1338 (2)0.75088 (12)0.30474 (14)0.0740 (6)
O30.19151 (18)0.77955 (8)0.12752 (12)0.0511 (4)
N60.08941 (19)0.78554 (9)0.20231 (13)0.0433 (4)
N10.4130 (4)0.41106 (12)0.9114 (2)0.0874 (7)
N20.5414 (2)0.63944 (7)0.48320 (12)0.0365 (3)
N30.50076 (18)0.68666 (7)0.37950 (12)0.0356 (3)
H30.38460 (18)0.69524 (7)0.33897 (12)0.0428 (4)*
N40.6058 (2)0.76428 (8)0.24555 (13)0.0409 (4)
H4a0.4889 (2)0.77271 (8)0.20653 (13)0.0490 (4)*
H4b0.6968 (2)0.78549 (8)0.22081 (13)0.0490 (4)*
N50.82308 (19)0.70476 (8)0.40629 (13)0.0400 (3)
H5a0.84588 (19)0.67518 (8)0.47013 (13)0.0480 (4)*
H5b0.91620 (19)0.72539 (8)0.38310 (13)0.0480 (4)*
C10.2356 (6)0.38566 (16)0.9365 (3)0.1026 (12)
H1a0.1575 (19)0.42840 (18)0.943 (3)0.1538 (18)*
H1b0.169 (2)0.3538 (13)0.8692 (14)0.1538 (18)*
H1c0.2630 (6)0.3579 (14)1.0138 (14)0.1538 (18)*
C20.5905 (6)0.38315 (15)0.9887 (3)0.0955 (11)
H2a0.6540 (19)0.3535 (13)0.9385 (6)0.1433 (16)*
H2b0.6705 (17)0.42474 (15)1.024 (2)0.1433 (16)*
H2c0.5656 (6)0.3526 (13)1.0546 (15)0.1433 (16)*
C30.4114 (4)0.45815 (10)0.8108 (2)0.0634 (6)
C40.2373 (4)0.48138 (11)0.7309 (2)0.0611 (6)
H40.1224 (4)0.46415 (11)0.7440 (2)0.0733 (7)*
C50.2372 (3)0.52957 (11)0.63359 (19)0.0525 (5)
H50.1209 (3)0.54447 (11)0.58139 (19)0.0630 (6)*
C60.4061 (3)0.55698 (9)0.61038 (16)0.0436 (4)
C70.5785 (3)0.53392 (10)0.68853 (17)0.0504 (5)
H70.6929 (3)0.55124 (10)0.67480 (17)0.0604 (6)*
C80.5807 (4)0.48495 (11)0.78743 (19)0.0601 (6)
H80.6972 (4)0.46975 (11)0.83901 (19)0.0721 (7)*
C90.3938 (2)0.60792 (9)0.50545 (15)0.0388 (4)
H90.2744 (2)0.61804 (9)0.45245 (15)0.0465 (5)*
C100.6459 (2)0.71842 (8)0.34418 (14)0.0328 (3)

Source of material

4-(Dimethylamino)benzaldehyde (1.49 g, 0.01 mol) was dissolved in 15 ml ethanol at room temperature, aminoguanidine nitrate (1.37 g, 0.01 mol) was put into the aqueous ethanol (10 ml water and 8 ml ethanol), heated at 60° centigrade, and stirred for 8 h, then cooled down to room temperature, finally we obtained the colorless transparent crystal.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Comment

Guanidine compounds, as an organic base and nitrogen-containing heterocyclic ligands, have been the research focus of chemistry [5], medicine [6] and materials science [7]. Because of their insensitivity and low flame temperature, high energy materials containing guanidine compounds can make significant contributions in the field of emerging propulsion technology [8]. More than 20 years ago, Tadao Taguchi et al. have synthesized aminoguanidine Schiff base from guanidine and pyrrolaldehyde, which has important biological toxicological significance [9]. In order to explore the properties of guanidine Schiff base ligands or even its complexes, we have synthesized a new ligand whose crystal structure has not been reported.

Bond lengths and angles in the title guanidinium salt are within normal ranges [10], [11]. The bond length between C9 and N2 is 1.282(2) Å, indicating that the reaction of Schiff base has taken place, and the C=N was also formed.


Corresponding author: Fang-fang Jian, School of Chemical Engineering and Pharmaceutics, Henan University of Science and Technology, Luoyang Hekeda Recycling Energy Co. LTD, Luoyang, Henan 471003, P. R. China, E-mail:

Funding source: Henan University of Science and Technology

Award Identifier / Grant number: 135100001

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

  2. Research funding: Henan University of Science and Technology Distinguished Professor Open Fund (Grant No. 135100001).

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

References

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Received: 2021-03-15
Accepted: 2021-04-08
Published Online: 2021-04-26
Published in Print: 2021-07-27

© 2021 Xiao-Jing Liu 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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