Home Physical Sciences Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
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Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2

  • Lufei Xiao ORCID logo , Jie Li , Qirui Liang and Jie Liu ORCID logo EMAIL logo
Published/Copyright: March 10, 2022

Abstract

C17H17N3O2, monoclinic, P21/c (no. 14), a = 10.655(5) Å, b = 5.056(5) Å, c = 28.712 Å, β = 99.034(1)°, V = 1527.6(17) Å3, Z = 4, R gt (F) = 0.0520, wR ref(F 2) = 0.1611, T = 298(2) K.

CCDC no.: 1851609

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: Colorless block
Size: 0.30 × 0.20 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker Smart Apex, ω
θ max, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, R int: 10,113, 2663, 0.033
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1943
N(param)refined: 227
Programs: Bruker [1], Olex2 [2], SHELX [3]
Table 2:

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

Atom x y z U iso*/U eq
C1Aa 0.0757 (5) 0.0162 (7) −0.05858 (12) 0.0932 (12)
H1Aa 0.081909 −0.074216 −0.030103 0.112*
C1Bb −0.0008 (8) 0.130 (2) −0.0625 (3) 0.063 (2)
H1Bb −0.044410 0.136482 −0.036883 0.075*
C2Aa 0.0112 (5) −0.0629 (10) −0.10036 (19) 0.0782 (13)
H2Aa −0.042280 −0.209061 −0.104756 0.094*
C2Bb −0.0379 (13) 0.020 (3) −0.1031 (6) 0.075 (4)
H2Bb −0.106062 −0.096709 −0.109572 0.090*
C3 0.1129 (3) 0.2678 (7) −0.11160 (8) 0.1042 (10)
H3 0.154129 0.394777 −0.127132 0.125*
C4 0.2051 (2) 0.4062 (4) −0.03099 (7) 0.0722 (6)
C5 0.1788 (3) 0.4169 (5) 0.01415 (7) 0.0974 (9)
H5 0.111548 0.318975 0.022229 0.117*
C6 0.2511 (3) 0.5714 (5) 0.04774 (8) 0.1027 (10)
H6 0.232183 0.576394 0.078266 0.123*
C7 0.3503 (3) 0.7171 (5) 0.03669 (9) 0.0877 (8)
C8 0.3760 (3) 0.7033 (8) −0.00882 (11) 0.1262 (13)
H8 0.443450 0.800059 −0.017069 0.151*
C9 0.3036 (3) 0.5488 (7) −0.04228 (10) 0.1161 (12)
H9 0.322503 0.542272 −0.072799 0.139*
C10 0.3899 (2) 0.9940 (5) 0.10190 (8) 0.0783 (7)
H10 0.302850 0.992150 0.102344 0.094*
C11 0.4732 (2) 1.1430 (4) 0.13828 (7) 0.0740 (7)
C12 0.6036 (3) 1.1094 (6) 0.14438 (9) 0.0933 (8)
H12 0.638103 0.989457 0.125324 0.112*
C13 0.6842 (3) 1.2497 (6) 0.17814 (9) 0.0940 (8)
H13 0.771565 1.223038 0.181844 0.113*
C14 0.6342 (3) 1.4269 (5) 0.20585 (8) 0.0896 (8)
H14 0.688017 1.524333 0.228102 0.107*
C15 0.5047 (3) 1.4634 (5) 0.20128 (7) 0.0821 (7)
H15 0.471542 1.584219 0.220550 0.099*
C16 0.4233 (2) 1.3198 (4) 0.16785 (7) 0.0718 (6)
C17 0.2357 (3) 1.5125 (6) 0.19105 (9) 0.1009 (9)
H17A 0.260398 1.459579 0.223290 0.151*
H17B 0.144949 1.501676 0.182859 0.151*
H17C 0.262619 1.691276 0.187145 0.151*
N1 0.12871 (18) 0.2476 (4) −0.06562 (6) 0.0704 (5)
N2 0.0348 (2) 0.0954 (5) −0.13374 (7) 0.0881 (7)
N3 0.4337 (2) 0.8684 (5) 0.07002 (8) 0.0993 (8)
O1 0.29396 (17) 1.3413 (4) 0.16099 (5) 0.0878 (6)
O3 0.0365 (2) 0.9465 (4) 0.23458 (7) 0.0980 (7)
H3A 0.006 (3) 0.944 (8) 0.2040 (14) 0.145 (13)*
H3B 0.008 (4) 1.121 (9) 0.2434 (14) 0.156 (14)*
  1. aOccupancy: 0.75, bOccupancy: 0.25.

Source of material

All chemicals were purchased from commercial sources and used as received without further purification. The 4-imidazol-1-yl-phenylamine (2.45 mmol, 0.39 g) and 2-methoxy-benzaldehyde (6.98 mmol, 0.95 g) were dissolved in EtOH (25 mL). The mixture was refluxed for 8 h, and then the precipitate was collected by filtration and washed with EtOH. The product was recrystallized from a mixture of ethyl acetate and cyclohexane to afford colorless crystals. Yield: 0.51 g (75.5%). m.p.: 84.1–85.5 °C. 1 H NMR (CDCl3, 400 MHz, ppm): δ 8.95 (s, 1H), 8.15 (dd, J = 7.76 Hz, 1.80 Hz, 1H), 7.89 (s, 1H), 7.48 (td, J = 7.88 Hz, 1.76 Hz, 1H), 7.41 (dt, J = 8.76 Hz, 2.68 Hz, 2H), 7.34–7.30 (m, 3H), 7.23–7.15 (m, 2H), 7.08–7.05 (m, 1H), 3.92 (s, 3H).

Experimental details

All H-atoms bonded to C-atoms were placed geometrically and refined using a riding model with common isotropic displacement factors U iso(H) = 1.2 or 1.5 U eq (parent C-atom).

Comment

The imidazole ring is broadly present in many natural products from a diversity of sources and is a key structural motif of essential biomolecules such as nucleic acids, purine, histamine, and histidine [4]. Imidazole-containing compounds feature relevant biological activities and show a lot of therapeutic activities [4], [5], [6]. Furthermore, due to their photophysical and chemical properties as well as their good thermal stability, the imidazole derivatives are functional materials [7], [8], [9]. The title compound was synthesized by the aldehyde-amine condensation reaction to give the Schiff base, which has wide research in biology and chemistry [10, 11].

The title molecule exhibits an E configuration. The bond length of C10=N3 is 1.262 Å. The diheral angle of the two aromatic rings is 50.71°. The angle of C11–C10=N3 and C7–N3=C10 are 121.54° and 119.69°, respectively. The bond length of C10–C11 is 1.468 Å, shorter than normal C–C single bonds (1.54 Å). The geometric parameters are similar to those seen in the structures of related compounds [12, 13].


Corresponding author: Jie Liu, School of Chemistry and Material Engineering, Fuyang Normal University, Fuyang, Anhui 236041, China, E-mail:

Award Identifier / Grant number: KJ2017ZD49

Award Identifier / Grant number: KJ2018A0842

Award Identifier / Grant number: KJ2019A0545

Funding source: National and Anhui College Student Innovation and Entrepreneurship Program

Award Identifier / Grant number: 202110371010

Award Identifier / Grant number: S202010371057

Funding source: The Ministry of Education Industry-University Cooperation Collaborative Education Project

Award Identifier / Grant number: 202101052045

Funding source: School Level Online and Offline Mixed First-class Courses of Organic Chemistry Experiment

Award Identifier / Grant number: 2020HEYL02

  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 the foundation programs as follows: Natural Science Research Program under Anhui Provincial Department of Education (KJ2017ZD49, KJ2018A0842, KJ2019A0545); National and Anhui College Student Innovation and Entrepreneurship Program (202110371010, S202010371057); The Ministry of Education Industry-University Cooperation Collaborative Education Project (202101052045); School Level Online and Offline Mixed First-class Courses of Organic Chemistry Experiment (2020HEYL02).

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

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Received: 2022-01-15
Accepted: 2022-02-07
Published Online: 2022-03-10
Published in Print: 2022-06-27

© 2022 Lufei Xiao 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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