Home Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
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Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5

  • Ze-Yi Lian and Wei-Na Wu ORCID logo EMAIL logo
Published/Copyright: April 5, 2023

Abstract

C17H17N5, monoclinic, P21/c (no. 14), a = 9.4347(9) Å, b = 15.6392(15) Å, c = 11.0939(11) Å, β =  100.215 ( 2 ) ° , V = 1611.0(3) Å3, Z = 4, R gt (F) = 0.0392, wR ref (F 2) = 0.1105, T = 296 K.

CCDC no.: 2251226

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: Red rod
Size: 0.25 × 0.12 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.0°, >99%
N(hkl)measured , N(hkl)unique, R int: 8087, 2837, 0.023
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2179
N(param)refined: 214
Programs: SHELX [1], Bruker [2]
Table 2:

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

Atom x y z U iso*/U eq
N1 0.45302 (14) −0.05812 (7) 0.22928 (11) 0.0542 (3)
N2 0.82583 (13) 0.02201 (8) 0.55349 (10) 0.0508 (3)
N3 0.93074 (19) −0.13704 (11) 0.76901 (16) 0.0837 (5)
N4 1.1906 (2) 0.06644 (13) 0.90620 (16) 0.1033 (6)
N5 0.99322 (17) 0.15520 (10) 0.65207 (14) 0.0648 (4)
H5A 0.915 (2) 0.1593 (12) 0.5930 (18) 0.078 (6)*
H5B 1.024 (2) 0.2030 (14) 0.6964(18) 0.091 (7)*
C1 0.35602 (16) −0.12407 (9) 0.18802 (13) 0.0505(4)
C2 0.24188 (18) −0.12403 (11) 0.09088 (15) 0.0617 (4)
H2 0.2211 −0.0763 0.0408 0.074*
C3 0.15956 (19) −0.19771 (12) 0.07087 (16) 0.0681 (5)
H3 0.0817 −0.1995 0.0065 0.082*
C4 0.19108 (19) −0.26816 (12) 0.14460 (16) 0.0670(5)
H4 0.1350 −0.3172 0.1290 0.080*
C5 0.30601(18) −0.26709(10) 0.24244(15) 0.0582(4)
H5 0.3262 −0.3148 0.2926 0.070*
C6 0.38949 (16) −0.19447 (9) 0.26406 (13) 0.0477 (4)
C7 0.51933 (16) −0.17412 (9) 0.36154(13) 0.0466 (4)
C8 0.54813 (16) −0.08085 (9) 0.33193 (12) 0.0458 (4)
C9 0.4809 (2) −0.18485 (11) 0.48919 (14) 0.0656 (5)
H9A 0.4030 −0.1471 0.4976 0.098*
H9B 0.5633 −0.1713 0.5503 0.098*
H9C 0.4523 −0.2429 0.4997 0.098*
C10 0.64776 (18) −0.23082 (11) 0.34572 (18) 0.0686 (5)
H10A 0.6249 −0.2896 0.3585 0.103*
H10B 0.7308 −0.2144 0.4044 0.103*
H10C 0.6678 −0.2239 0.2644 0.103*
C11 0.4462 (2) 0.02617 (11) 0.17427 (17) 0.0765 (6)
H11A 0.3665 0.0286 0.1072 0.111 (7)*
H11B 0.5341 0.0374 0.1448 0.118 (9)*
H11C 0.4334 0.0683 0.2344 0.129 (9)*
C12 0.64775 (16) −0.02544 (9) 0.39179 (13) 0.0514 (4)
H12 0.6512 0.0282 0.3562 0.062*
C13 0.74614 (16) −0.03963 (9) 0.50105 (13) 0.0498 (4)
H13 0.7540 −0.0939 0.5360 0.060*
C14 0.92156 (16) 0.00967 (10) 0.66198 (13) 0.0494 (4)
C15 1.00174 (16) 0.07803 (10) 0.70943 (13) 0.0521 (4)
C16 0.93162 (17) −0.07085 (11) 0.72491(15) 0.0588 (4)
C17 1.10605 (19) 0.07038 (12) 0.81975 (16) 0.0674 (5)

1 Source of material

The starting materials 1,3,3-trimethyl-2-(formylmethylene)indoline (2.01 g, 10 mmol) and diaminomaleonitrile (1.08 g, 10 mmol) in an ethanol solution (100 mL) were stirred for 5 h under refluxing. The formed red powder was filtered, and the mother liquid was left in air for a few days, yielding red rod crystals.

2 Experimental details

The structure was solved by Direct Methods and refined with the SHELX crystallographic software package [1]. The hydrogen atoms were placed at calculated positions and refined as riding atoms with isotropic displacement parameters.

3 Comment

Schiff bases have been extensively studied due to their excellent coordinative abilities, biological activities, and fluorescence properties, etc. [3]. Particularly, diaminomaleonitrile-based Schiff bases have been developed as fluorescent probes for the detection of Cu2+ [4] or ClO [5]. The title compound, derived from 1,3,3-trimethyl-2-(formylmethylene)indoline and diaminomaleonitrile, could act as a fluorescence turn-on probe for detecting Cu2+ [6].

In the title structure, the bond length of C13–N2 is 1.2953(18) Å (see the Figure), indicating the Schiff base formation. Bond lengths and angles are all in the expected ranges [7]. In the solid state, intermolecular N–H···N hydrogen bonds link the molecules into a chain along the b axis, which are further connected with each other by two types of intermolecular C–H···N hydrogen bonds to form a two-dimensional wave-like supermolecular network.


Corresponding author: Wei-Na Wu, College of Chemistry and Chemical Engineering, Henan Polytechnic University, Jiaozuo, 454000, P.R. China, E-mail:

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

  2. Research funding: None declared.

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

References

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Received: 2023-02-20
Accepted: 2023-03-23
Published Online: 2023-04-05
Published in Print: 2023-06-27

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

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