Home The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
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The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4

  • Ting Li , Xiyuan Xiao , Yuxing Tan ORCID logo EMAIL logo and Weiwei Fu EMAIL logo
Published/Copyright: February 22, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 3

Abstract

C28H21Cl2MnN5O4, triclinic, P 1 ‾ (no. 2), a = 8.9699(9) Å, b = 9.1185(9) Å, c = 17.6902(17) Å, α = 103.776(1)°, β = 92.407(1)°, γ = 99.761(1)°, V = 1379.8(2) Å3, Z = 2, R gt (F) = 0.0388, wR ref (F 2) = 0.0920, T = 296 K.

CCDC no.: 960789

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: Brown flake
Size: 0.27 × 0.14 × 0.01 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.72 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 26.0°, >99%
N(hkl)measured, N(hkl)unique, R int: 15,743, 5391, 0.031
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3790
N(param)refined: 365
Programs: Bruker [1], SHELX [2, 3], WinGX/ORTEP [4]
Table 2:

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

Atom x y z U iso*/U eq
Mn1 0.90839 (4) 0.87736 (4) 0.73447 (2) 0.04584 (12)
N1 0.68590 (19) 0.7772 (2) 0.66603 (10) 0.0412 (4)
N2 0.4572 (3) 0.7383 (3) 0.40281 (13) 0.0716 (7)
N3 0.8574 (2) 1.0971 (2) 0.81646 (11) 0.0500 (5)
N4 1.1470 (2) 0.9578 (2) 0.79103 (12) 0.0532 (5)
N5 1.0065 (2) 0.6693 (2) 0.66425 (11) 0.0489 (5)
O1 0.81630 (17) 0.76083 (18) 0.81432 (9) 0.0506 (4)
O2 0.91534 (17) 0.98725 (18) 0.64094 (9) 0.0540 (4)
O3 0.3623 (2) 0.6295 (3) 0.40842 (12) 0.0988 (8)
O4 0.4579 (3) 0.7908 (3) 0.34544 (12) 0.1103 (9)
Cl1 0.77116 (9) 0.75227 (8) 0.97543 (4) 0.0719 (2)
Cl2 0.20213 (9) 0.47483 (10) 0.86056 (5) 0.0873 (3)
C1 0.6778 (3) 0.7057 (2) 0.82290 (13) 0.0432 (5)
C2 0.6348 (3) 0.6849 (3) 0.89663 (13) 0.0497 (6)
C3 0.4939 (3) 0.6135 (3) 0.90843 (15) 0.0567 (7)
H3 0.472700 0.599283 0.957475 0.068*
C4 0.3833 (3) 0.5628 (3) 0.84630 (15) 0.0590 (7)
C5 0.4145 (3) 0.5888 (3) 0.77504 (14) 0.0552 (6)
H5 0.338393 0.557111 0.734167 0.066*
C6 0.5579 (2) 0.6617 (3) 0.76202 (13) 0.0442 (5)
C7 0.5704 (3) 0.6991 (3) 0.68731 (14) 0.0477 (6)
C8 0.6812 (2) 0.8171 (2) 0.59318 (12) 0.0400 (5)
C9 0.5714 (2) 0.7535 (3) 0.53241 (13) 0.0465 (6)
H9 0.494926 0.673277 0.535989 0.056*
C10 0.5741 (3) 0.8080 (3) 0.46587 (13) 0.0495 (6)
C11 0.6870 (3) 0.9273 (3) 0.45943 (14) 0.0563 (6)
H11 0.685673 0.965778 0.415273 0.068*
C12 0.8005 (3) 0.9882 (3) 0.51821 (14) 0.0549 (6)
H12 0.876615 1.067304 0.512988 0.066*
C13 0.8052 (2) 0.9343 (3) 0.58671 (13) 0.0446 (5)
C14 1.2415 (3) 1.0678 (4) 0.77175 (18) 0.0797 (9)
H14 1.207061 1.113351 0.734259 0.096*
C15 1.3886 (4) 1.1183 (5) 0.8046 (2) 0.1070 (13)
H15 1.452276 1.195396 0.789057 0.128*
C16 1.4388 (3) 1.0542 (5) 0.8595 (2) 0.0925 (11)
H16 1.537923 1.086272 0.882320 0.111*
C17 1.3432 (4) 0.9423 (4) 0.8813 (2) 0.0846 (10)
H17 1.374964 0.897227 0.919590 0.102*
C18 1.1981 (3) 0.8973 (3) 0.84525 (18) 0.0710 (8)
H18 1.132752 0.820262 0.859927 0.085*
C19 0.9735 (3) 0.5308 (3) 0.67817 (15) 0.0577 (7)
H19 0.909543 0.518650 0.717141 0.069*
C20 1.0279 (3) 0.4049 (3) 0.63867 (17) 0.0685 (8)
H20 1.002307 0.310469 0.650777 0.082*
C21 1.1207 (3) 0.4225 (4) 0.58112 (17) 0.0724 (8)
H21 1.159375 0.339393 0.553063 0.087*
C22 1.1565 (3) 0.5624 (4) 0.56493 (16) 0.0700 (8)
H22 1.219036 0.576226 0.525624 0.084*
C23 1.0980 (3) 0.6828 (3) 0.60804 (15) 0.0607 (7)
H23 1.123673 0.778551 0.597334 0.073*
C24 0.8110 (3) 1.2089 (3) 0.79109 (16) 0.0590 (7)
H24 0.794089 1.196707 0.737534 0.071*
C25 0.7872 (4) 1.3413 (3) 0.8404 (2) 0.0794 (9)
H25 0.753541 1.416764 0.820533 0.095*
C26 0.8133 (3) 1.3619 (3) 0.9192 (2) 0.0779 (9)
H26 0.798658 1.451798 0.953604 0.093*
C27 0.8610 (3) 1.2486 (3) 0.94643 (16) 0.0684 (8)
H27 0.880018 1.259567 0.999762 0.082*
C28 0.8803 (3) 1.1180 (3) 0.89351 (16) 0.0622 (7)
H28 0.911076 1.039909 0.912312 0.075*
H7 0.477 (3) 0.666 (3) 0.6537 (14) 0.065 (7)*

Source of material

All chemicals were purchased from commercial sources and used as received. A mixture of 2-amino-4-nitrophenol (10 mmol), 3,5-dichloro-2-hydroxybenzaldehyde (10 mmol) and CH3OH (50 mL) was added in a round-bottomed flask (100 mL), and refluxed with agitating for 4.0 h. The solution was cooled, and then the insoluble matter is removed by filtration. The ligand 2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenol was obtained. 1 mmol 2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenol and 1 mmol manganous acetate were added in CH3OH (50 mL) and refluxed with agitating for 2 h. Then, most of the methanol was evaporated, followed by adding pyridine dropwise until it just dissolved. The reaction solution continued to reflux for 2 h, then it was filtered. Finally, the title crystal was precipitated by controlling solvent volatilization.

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

There is a growing interest in the design and synthesis of novel Schiff base complexes due to their peculiar properties [5], [6], [7]. A variety of related compounds have been synthesized and investigated, in this aspect. The tridentate Schiff-base and its analogues are of special concern as they form stable coordination environments and controllable structures [8–12]. As a part of our current research on the exploration of the regulating effect of Schiff base ligands in transition metal complexes, we report a new Mn(II) complex.

Single-crystal structure analysis revealed that the title compound crystallized in the triclinic space group P 1 ‾ . The ORTEP diagram is presented in the figure. Bond lengths and angles are all in the expected ranges and similar to the isomorphous structure [13]. The ligand of the title molecule exhibits an E configuration. The bond length of C7=N1 is 1.278(3) Å, which is similar to those reported in the literature [14]. Mn1 is six-coordinated in form of a distorted octahedral geometry and it is surrounded by two oxygen atoms (O1 and O2) and one nitrogen atom (N1) from the chelating ligand, three nitrogen atoms (N3, N4, and N5) from three different pyridines. The axis position was occupied by two nitrogen atoms (N3 and N5) from two pyridines, respectively. The angle of N3–Mn1–N5 is 168.96(6)°. The four atoms (O1, O2, N1, and N4) were placed in equatorial sites, and the sum of the angles [O1–Mn1–N1 = 83.81(6)°, O2–Mn1–N1 = 76.46(6)°, O2–Mn1–N4 = 101.61(7)°, O1–Mn1–N4 = 99.00(7)°] is 360.88°, which shows that the four atoms are planar, but the bond lengths [Mn1–O1 = 2.0789(16) Å, Mn1–O2 = 2.1266(16) Å, Mn1–N1 = 2.2215(17) Å, Mn1–N4 = 2.2488(19) Å] are unequal, and the coordination mode is similar to that of a previously reported complex [15, 16].

Weak intermolecular and weak intermolecular hydrogen bonding exists in the crystal structure of the title compound. The carbon atom C24 provides one intramolecular hydrogen bond to O2 (C24⋯O2 = 3.211(3) Å). The carbon atom C15 provides one intermolecular hydrogen bond to O4′ of another molecule (C15⋯O4′ = 3.255(4) Å; ′ = −x + 2, −y + 2, −z + 1). The carbon atom C22 provides one intermolecular hydrogen bond to O3″ of another molecule (C22⋯O3″ = 3.508(4) Å; ″ = x + 1, y, z).

Corresponding authors: Yuxing Tan and Weiwei Fu, School of Chemistry and Materials Science, Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Metal Organic New Materials of College of Hunan Province, Hengyang Normal University, Hengyang, Hunan 421008, China, E-mail: ,

Funding source: Hunan College students Innovation

Award Identifier / Grant number: NYD202212

Funding source: Entrepreneurship Training Program

Award Identifier / Grant number: NYD202125

Funding source: Hunan Provincial Education Department of China

Award Identifier / Grant number: 20K016

  1. Author contribution: 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 Hunan College students Innovation and Entrepreneurship Training Program (Nos. NYD202212, NYD202125), the Innovation Platform Open Fund Project of Hunan Provincial Education Department of China (No. 20K016).

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

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Received: 2023-01-07
Accepted: 2023-02-06
Published Online: 2023-02-22
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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  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
https://doi.org/10.1515/ncrs-2023-0012
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,Nʹ,Nʺ]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N′1,N′3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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