Home The crystal structure of bis(2-oxidopyridin-1-ium-3-carboxylato-κ2O,O′)-(phenantroline-κ2N,N′)manganese(II) - methanol (1/3), C27H28N4O9Mn
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The crystal structure of bis(2-oxidopyridin-1-ium-3-carboxylato-κ2O,O′)-(phenantroline-κ2N,N′)manganese(II) - methanol (1/3), C27H28N4O9Mn

  • Xiaoxia Men , Zhongyu Zhang ORCID logo EMAIL logo , Xiaoli Li and Weiqin Sun
Published/Copyright: September 29, 2021

Abstract

C27H28N4O9Mn, monoclinic, P21/n (no. 14), a = 10.0269(7) Å, b = 14.1702(10) Å, c = 20.0750(14) Å, β = 100.298(1)°, V = 2806.4(3) Å3, Z = 4, R gt (F) = 0.0403, wR ref (F2) = 0.0985, T = 296.15 K.

CCDC no.: 2106414

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: Yellow block
Size: 0.15 × 0.15 × 0.15 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.530 mm−1
Diffractometer, scan mode: Bruker Smart APEX-II, φ and ω
θmax, completeness: 27.1°, >99%
N(hkl)measured, N(hkl)unique, Rint: 19,168, 6216, 0.041
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4175
N(param)refined: 376
Programs: Bruker [1], Olex2 [2]
Table 2:

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

Atom x y z Uiso*/Ueq
Mn1 0.48376 (3) 0.73084 (2) 0.16374 (2) 0.03437 (11)
O1 0.3942 (2) 0.75381 (13) 0.24930 (9) 0.0634 (5)
O2 0.26414 (18) 0.80029 (13) 0.31965 (8) 0.0582 (5)
O3 0.36297 (16) 0.85036 (11) 0.12491 (8) 0.0451 (4)
O4 0.66095 (16) 0.81310 (10) 0.18994 (8) 0.0473 (4)
O5 0.83807 (15) 0.86849 (9) 0.26015 (9) 0.0496 (4)
O6 0.61517 (14) 0.61866 (9) 0.20869 (8) 0.0375 (4)
O7 0.4710 (2) 0.74745 (18) 0.41799 (11) 0.0867 (7)
H7 0.413018 0.761581 0.385299 0.130*
O8 0.4176 (3) 0.67300 (16) 0.53196 (11) 0.0910 (7)
H8 0.428318 0.697868 0.496405 0.136*
O9 0.2685 (3) 0.5143 (2) 0.51818 (14) 0.1296 (11)
H9 0.312762 0.561086 0.532397 0.194*
N1 0.20155 (18) 0.96047 (12) 0.11013 (10) 0.0439 (5)
H1 0.220988 0.970154 0.070666 0.053*
N2 0.80018 (17) 0.53735 (11) 0.25538 (9) 0.0349 (4)
H2 0.751267 0.487145 0.249876 0.042*
N3 0.32079 (18) 0.62228 (12) 0.12078 (10) 0.0409 (5)
N4 0.50555 (18) 0.70051 (12) 0.05504 (9) 0.0377 (4)
C1 0.3022 (2) 0.80537 (16) 0.26436 (12) 0.0394 (5)
C2 0.2352 (2) 0.87733 (14) 0.21450 (11) 0.0346 (5)
C3 0.2732 (2) 0.89168 (14) 0.14943 (11) 0.0338 (5)
C4 0.1031 (3) 1.01403 (17) 0.12861 (14) 0.0543 (7)
H4 0.059626 1.059501 0.099039 0.065*
C5 0.0675 (3) 1.00217 (18) 0.18914 (15) 0.0584 (7)
H5 0.000343 1.039150 0.202496 0.070*
C6 0.1342 (2) 0.93276 (16) 0.23155 (13) 0.0459 (6)
H6 0.109203 0.923493 0.273493 0.055*
C7 0.7696 (2) 0.80239 (14) 0.23157 (11) 0.0327 (5)
C8 0.8230 (2) 0.70368 (13) 0.24784 (10) 0.0296 (4)
C9 0.7382 (2) 0.62157 (13) 0.23500 (10) 0.0285 (4)
C10 0.9318 (2) 0.52763 (15) 0.28331 (13) 0.0445 (6)
H10 0.966347 0.468012 0.295673 0.053*
C11 1.0141 (2) 0.60370 (15) 0.29357 (13) 0.0501 (6)
H11 1.105764 0.597434 0.311630 0.060*
C12 0.9564 (2) 0.69249 (15) 0.27603 (12) 0.0413 (5)
H12 1.011182 0.745756 0.283884 0.050*
C13 0.2287 (2) 0.58494 (18) 0.15313 (14) 0.0558 (7)
H13 0.224509 0.606717 0.196418 0.067*
C14 0.1379 (3) 0.5147 (2) 0.12534 (18) 0.0686 (9)
H14 0.075034 0.490223 0.149604 0.082*
C15 0.1434 (3) 0.48300 (19) 0.06220 (19) 0.0705 (9)
H15 0.085165 0.435225 0.043263 0.085*
C16 0.2366 (3) 0.52174 (16) 0.02507 (14) 0.0533 (7)
C17 0.3238 (2) 0.59197 (15) 0.05696 (12) 0.0406 (5)
C18 0.4214 (2) 0.63399 (14) 0.02179 (11) 0.0374 (5)
C19 0.4266 (3) 0.60586 (17) −0.04461 (13) 0.0503 (6)
C20 0.5214 (3) 0.6509 (2) −0.07692 (14) 0.0664 (8)
H20 0.527881 0.634613 −0.121097 0.080*
C21 0.6036 (3) 0.7181 (2) −0.04423 (15) 0.0651 (8)
H21 0.666086 0.748859 −0.065680 0.078*
C22 0.5932 (3) 0.74039 (17) 0.02208 (13) 0.0519 (6)
H22 0.651238 0.786011 0.044428 0.062*
C23 0.2474 (3) 0.49314 (19) −0.04183 (16) 0.0680 (9)
H23 0.190969 0.445737 −0.062895 0.082*
C24 0.3373 (3) 0.5332 (2) −0.07487 (15) 0.0676 (8)
H24 0.341783 0.513322 −0.118564 0.081*
C25 0.5989 (4) 0.7519 (3) 0.3999 (2) 0.1020 (12)
H25A 0.613324 0.814063 0.383456 0.153*
H25B 0.604237 0.706480 0.364995 0.153*
H25C 0.667059 0.738365 0.438711 0.153*
C26 0.4659 (4) 0.7328 (2) 0.58586 (17) 0.0874 (10)
H26A 0.554225 0.755548 0.581601 0.131*
H26B 0.471690 0.698946 0.627681 0.131*
H26C 0.405212 0.785294 0.585468 0.131*
C27 0.1883 (5) 0.4896 (3) 0.5621 (2) 0.1377 (17)
H27A 0.234153 0.502156 0.607448 0.207*
H27B 0.167776 0.423467 0.557373 0.207*
H27C 0.105777 0.525319 0.552964 0.207*

Source of material

2-Hydroxypyridine-3-carboxylic acid (2.0 mmol) was dissolved in 20 mL of methanol. Mn(CH3COO)2·4H2O (1.0 mmol) dissolved in 20 mL of methanol was added dropwise to the above 2-Hydroxypyridine-3-carboxylic acid solution and stirred for 4 h at 55 °C. Then 1,10-phenanthroline (1.0 mmol) was dissolved in 10 mL of methanol was added dropwise to the above solution and stirred for 4 h at 55 °C cooled and filtered. The filtrate was left for slow evaporation at room temperature. The yellow block crystals were formed 16 days later. Yield: 41.6%. Anal. Calcd. for C27H28N4O9Mn: C, 53.38; H, 4.65; N, 9.22; found: C, 53.60; H, 4.63; N, 9.21.

Experimental details

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

Comment

Complexes with heterocyclic ligands are worth for many reasons, chief among them are their biological activities [35]. Pyridine ring drugs have the ability to enhance the binding of drugs to biomacromolecules and resist cancer [6]. As a part of our current research on the biological activity of heterocyclic transition metal complexes, we report herein a new manganese complex.

Single crystal X-ray diffraction analysis demonstrates that the asymmetric unit of the title structure contains one manganese(II) cation, two 2-oxidopyridin-1-ium-3-carboxylate ligands, one 1,10-phenanthroline ligand and three methanol molecules (see the Figure). The bond distances of Mn–N are 2.2727(18)–2.2971(19) Å, bond lengths of Mn–O are 2.1010(17) and 2.1568(14) Å, respectively, which are similar to the reference [7], [8], [9]. In the title complex, the bond angles of O(3)–Mn(1)–O(6), O(1)–Mn(1)–N(4) and O(4)–Mn(1)–N(3), are 175.20(6), 160.52(7), 166.83(7)° respectively. The Mn (II) is six coordinated by four oxygen and two nitrogen atoms from the two 2-oxidopyridin-1-ium-3-carboxylate ligands and 1, 10-phenanthroline to furnish a distorted octahedron geometry [10]. In addition, there are three solvent methanol molecules not coordinating with metal ions in the complex.


Corresponding author: Zhongyu Zhang, Shandong Provincial Engineering Laboratory of Novel Pharmaceutical Excipients, Sustained and Controlled Release Preparations, College of Medicine and Nursing, Dezhou University, Dezhou, 253000, Shandong, China, E-mail:

Funding source: Dezhou University

Award Identifier / Grant number: 2016kjrc17

Funding source: Dezhou University

Award Identifier / Grant number: 3010040205

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

  2. Research funding: This study was supported by the Talent Introduction Program of Dezhou University (No. 2016kjrc17) and the Bidding subject of Dezhou University (No. 3010040205).

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

References

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Received: 2021-07-21
Accepted: 2021-09-09
Published Online: 2021-09-29
Published in Print: 2021-12-20

© 2021 Xiaoxia Men 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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  64. The crystal structure of (2a′S,2a1′S,3R,5a′S,7′R)-5-(furan-3-yl)-2a′,2a1′-dihydroxy-7′-methyldecahydro-2H-spiro[furan-3,6′-naphtho[1,8-bc]furan]-2,2′(2a′H)-dione, C19H22O7
  65. The crystal structure of 3-bromopicolinic acid, C6H4BrNO2
  66. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S,S) platinum(II), C26H18N6PtS4
  67. Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
  68. The crystal structure of 3-amino-5-carboxypyridin-1-ium bromide, C6H7BrN2O2
  69. The crystal structure of (2-hydroxy-5-methyl-phenyl)-(1H-pyrazol-4-yl)-methanone hemihydrate, C11H10.5N2O2.5
  70. Crystal structure of tetraaqua-(2-(4-formylphenoxy)acetato-k1O)cadmium(II), C18H22O12Cd
  71. Crystal structure of diethyl 6,12-dimethyl-3,9-di-p-tolyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5-dicarboxylate, C32H38N2O4
  72. Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5
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