Startseite Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
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Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2

  • Zhenyu Jin , Tanpeng Zhou und Yanju Liu ORCID logo EMAIL logo
Veröffentlicht/Copyright: 8. August 2024

Abstract

C22H24ZnN12Cl2, monoclinic, P21/n (no. 14), a = 8.3494(3) Å, b = 11.1678(3) Å, c = 27.8876(8) Å, β = 92.102(3)°, Z = 4, V = 2598.62(15) Å3, Rgt(F) = 0.0572, wRref(F2) = 0.1535, T = 293(2) K.

CCDC no.: 2372794

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: 0.28 × 0.21 × 0.19 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 3.52 mm−1
Diffractometer, scan mode: Xcalibur, ω
θmax, completeness: 67.1°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 9,733, 4,634, 0.038
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 3,867
N(param)refined: 338
Programs: SHELX 1
Table 2:

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

Atom x y z Uiso*/Ueq
Zn1 0.45933 (6) 0.20817 (5) 0.25717 (2) 0.03402 (17)
Cl1 0.24722 (15) 0.13393 (12) 0.29365 (5) 0.0541 (3)
Cl2 0.62042 (16) 0.06042 (12) 0.23485 (5) 0.0570 (3)
N1 1.0670 (6) 0.2610 (4) 0.45826 (16) 0.0602 (12)
N2 1.0337 (5) 0.3111 (5) 0.41720 (15) 0.0576 (11)
N3 0.9158 (5) 0.3937 (4) 0.42228 (13) 0.0466 (9)
N4 0.7220 (4) 0.4169 (3) 0.35620 (12) 0.0394 (8)
N5 0.5755 (5) 0.4704 (4) 0.36065 (13) 0.0465 (9)
N6 0.5658 (4) 0.3250 (3) 0.30510 (11) 0.0353 (7)
N7 −0.0565 (6) 0.2636 (4) 0.03692 (17) 0.0600 (12)
N8 −0.0143 (5) 0.3149 (4) 0.07724 (15) 0.0532 (10)
N9 0.1053 (4) 0.3948 (4) 0.06901 (13) 0.0427 (9)
N10 0.2869 (4) 0.4016 (3) 0.13821 (11) 0.0362 (8)
N11 0.4472 (4) 0.4157 (3) 0.13093 (12) 0.0380 (8)
N12 0.4042 (4) 0.3069 (3) 0.19695 (11) 0.0324 (7)
C1 0.7590 (6) 0.4642 (5) 0.49329 (18) 0.0545 (13)
H1 0.6945 0.5214 0.4779 0.065*
C2 0.7511 (8) 0.4405 (6) 0.5415 (2) 0.0659 (16)
H2 0.6775 0.4821 0.5594 0.079*
C3 0.8506 (8) 0.3554 (5) 0.56451 (18) 0.0645 (17)
H3 0.8415 0.3431 0.5973 0.077*
C4 0.9588 (8) 0.2907 (5) 0.54090 (18) 0.0627 (16)
H4 1.0238 0.2344 0.5567 0.075*
C5 0.9693 (6) 0.3119 (4) 0.49128 (16) 0.0485 (11)
C6 0.8703 (6) 0.3968 (4) 0.46910 (15) 0.0438 (11)
C7 0.8627 (6) 0.4652 (5) 0.38219 (16) 0.0521 (12)
H7A 0.9496 0.4724 0.3602 0.063*
H7B 0.8379 0.5450 0.3935 0.063*
C8 0.7170 (5) 0.3315 (4) 0.32265 (13) 0.0350 (9)
C9 0.4861 (6) 0.4122 (4) 0.32903 (15) 0.0406 (10)
C10 0.8530 (5) 0.2577 (5) 0.30884 (17) 0.0499 (12)
H10A 0.9456 0.3076 0.3056 0.075*
H10B 0.8275 0.2190 0.2788 0.075*
H10C 0.8749 0.1983 0.3331 0.075*
C11 0.3119 (6) 0.4407 (5) 0.3213 (2) 0.0593 (14)
H11A 0.2900 0.4592 0.2881 0.089*
H11B 0.2849 0.5083 0.3407 0.089*
H11C 0.2490 0.3728 0.3303 0.089*
C12 0.2473 (7) 0.4608 (5) −0.00485 (19) 0.0581 (14)
H12 0.3171 0.5169 0.0090 0.070*
C13 0.2428 (9) 0.4347 (6) −0.0536 (2) 0.076 (2)
H13 0.3137 0.4739 −0.0732 0.092*
C14 0.1354 (10) 0.3515 (7) −0.0742 (2) 0.082 (2)
H14 0.1357 0.3384 −0.1072 0.098*
C15 0.0322 (9) 0.2903 (5) −0.0479 (2) 0.0714 (19)
H15 −0.0380 0.2348 −0.0620 0.086*
C16 0.0334 (6) 0.3125 (4) 0.00152 (18) 0.0504 (12)
C17 0.1390 (6) 0.3964 (4) 0.02149 (15) 0.0423 (10)
C18 0.1699 (6) 0.4658 (4) 0.10808 (16) 0.0471 (11)
H18A 0.0828 0.4920 0.1276 0.057*
H18B 0.2201 0.5366 0.0952 0.057*
C19 0.2622 (5) 0.3386 (4) 0.17776 (14) 0.0359 (9)
C20 0.5137 (5) 0.3556 (4) 0.16727 (14) 0.0365 (9)
C21 0.1030 (5) 0.3099 (5) 0.19575 (17) 0.0518 (12)
H21A 0.0539 0.3816 0.2072 0.078*
H21B 0.1143 0.2531 0.2215 0.078*
H21C 0.0370 0.2762 0.1703 0.078*
C22 0.6913 (5) 0.3448 (6) 0.17417 (18) 0.0549 (13)
H22A 0.7259 0.3881 0.2024 0.082*
H22B 0.7422 0.3775 0.1468 0.082*
H22C 0.7199 0.2620 0.1778 0.082*

1 Source of materials

All starting materials are commercially available without further purification. 1-[(3,5-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole (dtmb) was prepared according to the literature method with some modifications. 2 The ligand 1-[(3,5-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole (0.04 mmol, 0.0091 g) was dissolved in 2 mL of methanol solution and the solution was slowly added to 2 mL of ZnCl2 (0.04 mmol, 0.0054 g) of methanol solution. The prepared solution was placed at room temperature and colorless crystals were obtained after 2 weeks.

2 Experimental details

H atoms were generated geometrically and introduced as riding atoms with C–H = 0.93 Å and Uiso(H) = 1.2 times Ueq(C) for aromatic H atoms, with C–H = 0.97 Å and Uiso(H) = 1.2 times Ueq(C) for methylene H atoms, and with C–H = 0.96 Å and Uiso(H) = 1.5 times Ueq(C) for methyl H atoms.

3 Comment

As a type of nitrogen heterocyclic compound, benzotriazole derivatives exhibit strong coordination abilities and can effectively interact with transition metals to form a variety of metal complexes. For example, the Fei Wang team successfully synthesized four metal complexes by substituting benzotriazole as a ligand; 3 the Juan Xiao team successfully synthesized three copper metal complexes by benzotriazole-5-carboxylic acid as a ligand; 4 the Chun-Li Liu team successfully synthesized two zinc metal complexes by 1-[(benzotriazol-1-yl)methyl]-1H-imidazole as ligand. 5 In addition, benzotriazole derivatives exhibit a wide range of biological activities, including antibacterial, 6 antidiabetic 7 and anti-cancer. 8

X-ray crystallographic analysis shows that the title complex has a mononuclear asymmetric unit structure centered on Zn(II). As shown in the figure the Zn(II) is coordinated with two Cl ions (Cl1, and Cl2) and two N atoms (N6 and N12 from two dtmb ligands, respectively). The Zn–Cl and Zn–N bonds around Zn1 are of length: Zn1–Cl1: 2.2340(13) Å; Zn1–Cl2: 2.2317(13) Å; Zn1–N6: 2.047(3) Å; Zn1–N12: 2.048(3) Å. The range of bond angles around the metal center Zn(II) is 105.75(14)°–114.54(10)°. In each dtmb ligand, the angle between the benzotriazole ring and the imidazole ring is 58.80(13)°. The distance between the benzotriazole rings of two adjacent molecules is 3.5608 Å and 3.5853 Å, respectively, so it can be inferred that there may be two kinds of π–π interaction between the two molecules.


Corresponding author: Yanju Liu, College of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, P.R. China, E-mail:

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

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

  3. Research funding: Key Scientific and Research Projects of the Education Department of Henan Province (No. 21A430024).

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Received: 2024-05-13
Accepted: 2024-07-23
Published Online: 2024-08-08
Published in Print: 2024-10-28

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
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  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O:O)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
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  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
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  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
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  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
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  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
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  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
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  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
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