Home Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
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Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4

  • Shi-Lin Zhang ORCID logo EMAIL logo
Published/Copyright: November 25, 2022

Abstract

C32H54N8O4ZnBr4, triclinic, P 1 (no. 2), a = 8.250(5) Å, b = 12.289(10) Å, c = 20.954(14) Å, α = 82.36(2)°, β = 81.977(14)°, γ = 86.96(2)°, V = 2084(2) Å3, Z = 2, Rgt (F) = 0.0525, wRref (F 2) = 0.1419, T = 150(2) K.

CCDC no.: 2217903

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 needle
Size: 0.25 × 0.07 × 0.05 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 4.47 mm−1
Diffractometer, scan mode: φ and ω
θ max, completeness: 28.3°, >99%
N(hkl) measured, N(hkl) unique, R int: 33,142, 10,337, 0.073
Criterion for I obs, N(hkl) gt: I obs > 2 σ(I obs), 6821
N(param) refined: 454
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
Zn1 0.21440 (7) 0.72753 (4) 0.06676 (3) 0.01932 (14)
Br1 −0.06650 (6) 0.77393 (4) 0.11059 (3) 0.02617 (13)
Br2 0.39786 (7) 0.81167 (5) 0.12371 (3) 0.03355 (15)
Br3 0.25851 (7) 0.53311 (4) 0.08418 (3) 0.03266 (15)
Br4 0.25951 (7) 0.80480 (5) −0.04349 (3) 0.03553 (15)
O1 0.5372 (4) 0.1638 (3) 0.29327 (19) 0.0267 (8)
H1 0.6280 0.1369 0.2781 0.040*
O2 0.9641 (4) 0.1752 (3) 0.18671 (18) 0.0280 (8)
O3 0.0875 (5) 0.5359 (3) 0.41382 (19) 0.0366 (10)
H3D 0.1624 0.5362 0.3822 0.055*
O4 0.5441 (5) 0.4958 (3) 0.29756 (19) 0.0362 (10)
N1 −0.0102 (5) 0.0670 (3) 0.3723 (2) 0.0250 (10)
N2 0.7218 (5) 0.0322 (3) 0.2252 (2) 0.0208 (9)
N3 0.8589 (5) 0.0095 (3) 0.1827 (2) 0.0220 (9)
H3 0.8757 −0.0554 0.1691 0.026*
N4 1.2331 (5) 0.1313 (3) 0.08634 (19) 0.0173 (8)
N5 −0.4631 (5) 0.6632 (4) 0.4677 (2) 0.0250 (9)
N6 0.2367 (6) 0.5965 (4) 0.2951 (2) 0.0284 (10)
N7 0.3596 (6) 0.5983 (4) 0.2431 (2) 0.0304 (11)
H7 0.3417 0.6339 0.2053 0.036*
N8 0.7176 (5) 0.4621 (3) 0.1691 (2) 0.0222 (9)
C1 −0.0912 (8) 0.2650 (5) 0.3529 (3) 0.0407 (15)
H1A −0.0041 0.2775 0.3161 0.061*
H1B −0.1098 0.3313 0.3747 0.061*
H1C −0.1923 0.2481 0.3373 0.061*
C2 −0.0406 (6) 0.1695 (4) 0.4006 (3) 0.0264 (12)
H2A 0.0600 0.1881 0.4170 0.032*
H2B −0.1280 0.1587 0.4381 0.032*
C3 −0.1353 (7) −0.0880 (5) 0.4475 (3) 0.0314 (13)
H3A −0.0353 −0.1347 0.4428 0.047*
H3B −0.2312 −0.1342 0.4561 0.047*
H3C −0.1337 −0.0454 0.4837 0.047*
C4 −0.1439 (6) −0.0104 (5) 0.3854 (3) 0.0284 (12)
H4A −0.1388 −0.0538 0.3485 0.034*
H4B −0.2501 0.0313 0.3887 0.034*
C5 0.1411 (6) 0.0391 (4) 0.3409 (2) 0.0217 (10)
C6 0.2689 (6) 0.1133 (4) 0.3311 (2) 0.0204 (10)
H6 0.2495 0.1834 0.3457 0.025*
C7 0.4210 (6) 0.0863 (4) 0.3007 (2) 0.0195 (10)
C8 0.4562 (6) −0.0161 (4) 0.2761 (2) 0.0196 (10)
C9 0.3265 (6) −0.0887 (4) 0.2864 (2) 0.0213 (10)
H9 0.3452 −0.1581 0.2709 0.026*
C10 0.1737 (6) −0.0641 (4) 0.3176 (2) 0.0242 (11)
H10 0.0900 −0.1161 0.3235 0.029*
C11 0.6077 (6) −0.0388 (4) 0.2375 (2) 0.0185 (10)
H11 0.6250 −0.1071 0.2205 0.022*
C12 0.9676 (6) 0.0906 (4) 0.1627 (2) 0.0218 (10)
C13 1.0858 (6) 0.0615 (4) 0.1048 (2) 0.0219 (11)
H13A 1.1242 −0.0159 0.1143 0.026*
H13B 1.0253 0.0664 0.0669 0.026*
C14 1.3337 (7) 0.1205 (5) 0.1416 (3) 0.0291 (12)
H14A 1.2718 0.1527 0.1784 0.044*
H14B 1.4359 0.1592 0.1276 0.044*
H14C 1.3588 0.0427 0.1549 0.044*
C15 1.1887 (7) 0.2492 (4) 0.0670 (3) 0.0273 (12)
H15A 1.1169 0.2548 0.0331 0.041*
H15B 1.2884 0.2894 0.0503 0.041*
H15C 1.1316 0.2808 0.1049 0.041*
C16 1.3327 (6) 0.0896 (4) 0.0285 (2) 0.0233 (11)
H16A 1.3644 0.0122 0.0397 0.035*
H16B 1.4312 0.1326 0.0156 0.035*
H16C 1.2674 0.0967 −0.0076 0.035*
C17 −0.6021 (7) 0.8499 (5) 0.4551 (3) 0.0363 (14)
H17A −0.5126 0.8807 0.4232 0.054*
H17B −0.5825 0.8610 0.4988 0.054*
H17C −0.7060 0.8868 0.4458 0.054*
C18 −0.6102 (7) 0.7278 (5) 0.4513 (3) 0.0323 (13)
H18A −0.7062 0.6989 0.4813 0.039*
H18B −0.6274 0.7176 0.4067 0.039*
C19 −0.3811 (8) 0.6825 (5) 0.5763 (3) 0.0356 (14)
H19A −0.2688 0.6972 0.5558 0.053*
H19B −0.3788 0.6425 0.6199 0.053*
H19C −0.4432 0.7522 0.5795 0.053*
C20 −0.4616 (7) 0.6143 (4) 0.5357 (3) 0.0264 (11)
H20A −0.4039 0.5416 0.5362 0.032*
H20B −0.5760 0.6023 0.5561 0.032*
C21 −0.3253 (6) 0.6589 (4) 0.4231 (2) 0.0216 (10)
C22 −0.1836 (6) 0.5995 (4) 0.4394 (3) 0.0249 (11)
H22 −0.1831 0.5620 0.4820 0.030*
C23 −0.0450 (6) 0.5947 (4) 0.3945 (2) 0.0225 (11)
C24 −0.0398 (6) 0.6510 (4) 0.3309 (2) 0.0233 (11)
C25 −0.1822 (6) 0.7094 (4) 0.3156 (3) 0.0251 (11)
H25 −0.1830 0.7471 0.2730 0.030*
C26 −0.3204 (7) 0.7145 (4) 0.3596 (3) 0.0260 (11)
H26 −0.4141 0.7559 0.3472 0.031*
C27 0.1022 (7) 0.6477 (4) 0.2825 (3) 0.0277 (12)
H27 0.0965 0.6844 0.2400 0.033*
C28 0.5057 (6) 0.5472 (4) 0.2485 (3) 0.0242 (11)
C29 0.6173 (7) 0.5630 (4) 0.1842 (3) 0.0255 (11)
H29A 0.5497 0.5859 0.1489 0.031*
H29B 0.6920 0.6231 0.1850 0.031*
C30 0.6138 (8) 0.3637 (5) 0.1810 (3) 0.0380 (15)
H30A 0.5755 0.3478 0.2276 0.057*
H30B 0.6784 0.3004 0.1661 0.057*
H30C 0.5193 0.3782 0.1571 0.057*
C31 0.8577 (7) 0.4452 (5) 0.2087 (3) 0.0380 (14)
H31A 0.9348 0.5044 0.1947 0.057*
H31B 0.9141 0.3744 0.2025 0.057*
H31C 0.8155 0.4456 0.2548 0.057*
C32 0.7876 (7) 0.4790 (5) 0.0980 (3) 0.0297 (12)
H32A 0.6983 0.4841 0.0713 0.044*
H32B 0.8617 0.4167 0.0879 0.044*
H32C 0.8482 0.5470 0.0886 0.044*

Source of material

[(4-Diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium chloride (0.0342 g, 0.1 mmol) and zinc bromide (0.0222 g, 0.1 mmol) was dissolved in an methanol solution (2 ml). The mixture was stirred for 1 h at room temperature. The resulting solution was left in air for a few days, yielding colorless needle-shaped crystals.

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.

Comment

Complexes of d-metals with Schiff bases derived from trimethylammonium acetohydrazide chloride (Girard’s T reagent) have been extensively investigated due to their excellent water solubility, magnetic, antibacterial and anticancer properties [3, 4]. In addition, the Schiff base of [(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium, (C16H27N4O2)+, has been developed as a probe for the fluorescent detection of Zn2+ and S2− [5]. In this work, its tetrabromozincate salt was synthesized and characterized by X-ray diffraction.

As shown in Figure 1, the title complex is formed by one [ZnBr4]2− anion and two (C16H27N4O2)+ cations, the structure of which are similar as that demonstrated in its nitrate salt, namely (C16H27N4O2)NO3 [5]. In the crystal, the anions and cations are connected via electrostatic interaction, together with intermolecular N3–H3…Br1 i (symmetry code i: x + 1, y − 1, z) and N7–H7…Br2 hydrogen bonds to stabilize the structures. In addition, intermolecular O1–H1…N2 and O3–H3D…N6 hydrogen bonds are also present. All geometric parameters are in the expected ranges [6].


Corresponding author: Shi-Lin Zhang, Department of Architecture, Lyuliang University, Lyuliang, 033001, 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: 2022-09-30
Accepted: 2022-11-07
Published Online: 2022-11-25
Published in Print: 2023-01-27

© 2022 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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