Structures of substituted pyridine N-oxide with manganese(II) acetate

Lynch, W.; Lynch, G.; Sheriff, K.; Padgett, C.

doi:10.1107/S205698901801232X

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ISSN: 2056-9890

Volume 74| Part 10| October 2018| Pages 1405-1410

https://doi.org/10.1107/S205698901801232X

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Structures of substituted pyridine N-oxide with manganese(II) acetate

Will Lynch,^a ^* Genevieve Lynch,^b Kirk Sheriff ^a and Clifford Padgett ^a

^aDepartment of Chemistry and Biochemistry, Georgia Southern University, 11935 Abercorn Street, Savannah, GA 31419, USA, and ^bSt. Vincent's Academy, Savannah, 31401 Georgia, USA
^*Correspondence e-mail: wlynch@georgiasouthern.edu

Edited by M. Zeller, Purdue University, USA (Received 24 April 2018; accepted 30 August 2018; online 11 September 2018)

Manganese(II) acetate coordination polymers have been prepared with three derivatives of pyridine N-oxide. The compounds are catena-poly[manganese(II)-μ₃-acetato-di-μ₂-acetato-[aquamanganese(II)]-μ₂-acetato-μ-(pyridine N-oxide)-manganese(II)-μ₃-acetato-μ₂-acetato-μ-(pyridine N-oxide)-[aquamanganese(II)]-di-μ₂-acetato], [Mn₄(CH₃COO)₈(C₅H₅NO)₂(H₂O)₂]_n, (I), catena-poly[[manganese(II)]-μ₃-acetato-μ₂-acetato-μ-(2-methylpyridine N-oxide)-[aquamanganese(II)]-di-μ₂-acetato-manganese(II)-di-μ₂-acetato-μ₃-acetato-[aquamanganese(II)]-μ₂-acetato-μ-(2-methylpyridine N-oxide)], [Mn₄(CH₃COO)₈(C₆H₇NO)₂(H₂O)₂]_n, (II), and catena-poly[[manganese(II)-di-μ₂-acetato-μ-(4-methylpyridine N-oxide)] monohydrate], {[Mn(CH₃COO)₂(C₆H₇NO)]·H₂O}_n, (III). Compounds (I) and (II) both have three unique Mn atoms; in both compounds two of them sit on a crystallographic inversion center while the third is on a general position. In compound (III), the single unique Mn atom sits on a general position. Pseudo-octahedral six-coordinate manganese(II) centers are found in all compounds. All of the compounds form chains of Mn atoms bridged by acetate ions and the oxygen atom of the N-oxide in pyridine N-oxide (PNO), 2-methylpyridine N-oxide (2MePNO), or 4-methylpyridine N-oxide (4MePNO). Compound (I) and (II) both exhibit a bound water of solvation. In (I), the water hydrogen bonds to a nearby acetate whereas in (II) the water molecule forms bridging hydrogen bonds between two neighboring acetates. In compound (III) a water molecule of solvation is found in the lattice, not bound to the metal ion but hydrogen bonding to a bridging acetate.

Keywords: crystal structure; manganese(II) acetate; pyridine N-oxide ligand; coordination polymer.

CCDC references: 1864753; 1864752; 1864751

1. Chemical context

N-Oxides and acetates both have interesting binding modes that facilitate the growth of unique coordination structures. The structures take advantage of the versatility of the acetate ions and the hybridization and dipole at the oxygen atom on the N-oxide. The structures extend to the formation of coordination polymers that have been reported previously (Sarma et al., 2008 , 2009 ; Sarma & Baruah, 2011 ). A recent report shows the utility of pyridine N-oxide to facilitate coordination polymer formation with both zinc(II) and manganese(II) metal ions with a single bifunctional ligand containing an acetate and N-oxide moiety (Ren et al., 2018 ). In a previous paper in this series, we examined the initial utility of aromatic N-oxide ligands to form polymeric structures with manganese(II) chloride (Kang et al., 2017 ). Complexes have also been used previously as metal centers for catalytic transformations (Liu et al., 2014 ).

In this contribution, we report the synthesis and solid-state structures of three manganese(II) complexes with the versatile mono- or bidentate bridging ligands acetate and three derivatives of pyridine N-oxide (Figs. 1–3 ). In this study, each of the ligands pyridine N-oxide, 2-methyl and 4-methyl pyridine N-oxide has an impact on the structures of manganese(II) acetate complexes. All three complexes form coordination polymers with the N-oxide bridging in a μ₂-1,1 mode and varying acetate ligation. The study was conducted to investigate the utility of both acetate and substituted pyridine N-oxide to facilitate the growth of unique coordination polymers.

Figure 1
A view of compound I, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level, H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) −x + 1, –y + 1, −z + 1; (ii) x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , z; (iii) −x + $[{3\over 2}]$ , −y + $[{1\over 2}]$ , −z + 1.]

Figure 2
A view of compound II, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level, H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) −x + 1, −y, −z + 2.]

Figure 3
A view of compound III, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level, H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) −x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ .]

2. Structural commentary

General structural details. The pyridine N-oxide (PNO) complex, compound I, is a repeating tetrameric coordination polymer that crystallizes in the monoclinic space group C2/c. The manganese atoms align as an Mn3, Mn2, Mn1, Mn2, chain. The structure can be formulated in the simplest empirical relationship as [Mn₄(PNO)₂(OAc)₈(H₂O)₂]_n. Examining the molecule across the AB vertex, Mn3 and Mn1 sit in a repeating line of Mn3, Mn1, Mn3 atoms. The Mn2 atoms all sit along a different line in this orientation. The atom-to-atom connectivity in the Mn3,Mn2,Mn1,Mn2 repeating unit can best be described as zigzag (Fig. 4). In this orientation, the pyridine rings also stack; however, they are not π stacked because of the separation distance caused by the methyl group of an acetate ligand in between each aromatic group. Interpolymeric chain hydrogen bonding is observed from the water molecule (O10) on Mn2 to an oxygen atom (O6) on an Mn2-bound acetate ligand (Table 1). The structure contains a six-coordinate metal center at each Mn^II atom with all six donor atoms being oxygen. Mn1 sits on an inversion center and is bound trans by two μ₂-1,1-PNOs (to Mn2), trans by two μ₂-1,3-acetates (to Mn2), and trans by two μ₃-1,3,3-acetates (to both Mn2 and Mn3). Mn2 is also six-coordinate with a μ₂-1,1-PNO (from Mn1), a μ₂-1,3-acetate (from Mn1), and a μ₃-1,3,3-acetate (from Mn1 and Mn3). Further, the octahedral environment is completed by a water of hydration, a μ₂-1,1-acetate (to Mn3), and a μ₂-1,3-acetate (to Mn3). Mn3 also sits on an inversion cente, showing an octahedral enviroment where all the six coordinated oxygen atoms belong to acetate ligands. The coordination sphere comprises two μ₃-1,3,3-acetates (uniquely bound to Mn2 and Mn1), two μ₂-1,1-acetates (to Mn2) and two μ₂-1,3-acetates (to Mn2).

Table 1
Hydrogen-bond geometry (Å, °) for I

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10A⋯O9ⁱ	0.85 (2)	1.85 (2)	2.652 (2)	157 (3)
O10—H10B⋯O6ⁱⁱ	0.83 (2)	1.98 (2)	2.786 (2)	166 (3)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Figure 4
Crystal packing diagram of compound I, viewed along the b axis. Displacement ellipsoids are drawn at the 50% probability level, H atoms not involved in hydrogen bonding have been omitted for clarity, hydrogen bonds are rendered in blue.

The 2-methylpyridine N-oxide (2MePNO) complex, compound II, is similar to I in that it is a repeating tetrameric coordination polymer. The polymer crystallizes in the triclinic system, space group P $[\overline{1}]$ . The manganese atoms align as an Mn3, Mn2, Mn1, Mn2 chain similar to I with Mn1 and Mn3 sitting on inversion centers. Examining the molecule across the BC vertex, as in I, the Mn3 and Mn1 sit in a line whereas the Mn2 atoms all sit along a different line with respect to this orientation. The atom-to-atom connectivity in the Mn3, Mn2, Mn1, Mn2 repeating unit can best be described as zigzag (Fig. 5). In this orientation, the 2-methylpyridine ring planes are twisted by 85.31 (2)° with respect to the Mn1/O2/Mn2 plane with all the methyl groups pointing in two symmetry-related directions. As observed in I, interpolymeric chain hydrogen bonding is observed from the water molecule (O10) on Mn2 to an oxygen atom on the adjacent Mn2 on the next polymer. However, symmetry dictates that the hydrogen bonding is to oxygen atoms (O5 and O8) on two acetates bound to Mn2 (Table 2). The structure can be formulated with the same empirical stoichiometry as I, [Mn₄(2MePNO)₂(OAc)₇(H₂O)₄]_n. Compound II has one important variation from the PNO derivative outlined above. There is no evidence of the μ₂-1,1-acetate bridge found above. While the singular μ₃-1,3,3-acetate bridge is retained between Mn2 and Mn3, the μ₂-1,1 has been replaced by a μ₂-1,3 acetate bridge. This is likely because of the steric demands of the 2-methyl substituent.

Table 2
Hydrogen-bond geometry (Å, °) for II

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10D⋯O5ⁱ	0.84 (2)	2.04 (2)	2.821 (3)	155 (3)
O10—H10E⋯O8ⁱ	0.85 (2)	1.94 (2)	2.727 (3)	155 (3)
Symmetry code: (i) -x+1, -y, -z+1.

Figure 5
Crystal packing diagram of compound II, viewed along the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity, hydrogen bonds are rendered in blue.

The 4-methylpyridine N-oxide (4MePNO) complex, compound III, is a repeating coordination polymer with one unique Mn^II ion that crystallizes in the monoclinic system, space group P2₁/n. In the coordination polymer, the manganese atoms are aligned along the b-axis direction. The structure can be formulated as [Mn(4MePNO)₂(OAc)₄(H₂O)]_n. The six-coordinate metal center is bridged by two oxygen atoms from μ₂-1,1 4MePNO and four μ₂-1,3 acetate bridges. The 4MePNO complex molecules alternate above and below the line formed by the manganese atoms. Unlike I and II, compound III only forms intramolecular hydrogen bonding in the polymeric chain (Table 3, Fig. 6). The water observed in the lattice forms a hydrogen bond at 2.21 (2) Å with the O2 atom belonging to one of the acetate μ₂-1,3 acetate bridges.

Table 3
Hydrogen-bond geometry (Å, °) for III

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6D⋯O3ⁱ	0.84 (2)	2.23 (2)	3.052 (3)	165 (4)
O6—H6E⋯O2	0.84 (2)	2.21 (2)	3.035 (3)	170 (4)
Symmetry code: (i) x, y+1, z.

Figure 6
Crystal packing diagram of compound III, viewed along the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity, hydrogen bonds are rendered in blue.

Specific structural details. In I, the bond distances involving Mn1 lie between 2.1822 (15) Å (Mn1—O2) and 2.1207 (16) Å (Mn1—O4) whereas all bond angles are within 2.5° of 90°. These angles and distances are similar to those for other Mn^II acetate structures (see for example Dave et al., 1993 and Ciunik & Głowiak, 1980 ). The O1 atom of the PNO ligand bridges Mn1 at 2.168 (2) Å and Mn2 at 2.211 (2) Å which is unremarkable for compounds of Mn^II and pyridine N-oxide (Sniekers et al., 2017 ; Mondal et al., 2012 ). Mn2 shows a short bond distance to O5 (a μ₂-1,3-acetate bridging from Mn1) of 2.1062 (15) Å and a long distance of 2.2671 (14) Å from O8, which is a μ₂-1,1-acetate bridging to Mn3. The water molecule (O10), see Table 1, is found at 2.1506 (16) Å at a distance similar to that reported previously. (Mondal et al., 2012) and also hydrogen bonded to O9 (unbound acetate oxygen from μ₂-1,1-acetate bridging across Mn2 and Mn3) at 2.652 (2) Å. The O3—Mn2—O10 bond angle is severely distorted from 180° to 162.68 (6)°. The other two trans bond angles around Mn2 are approximately 175°. The Mn3 bond distances span from 2.1338 (15) (Mn3—O7) to 2.2194 (14) Å (Mn3—O8). The O3—Mn3—O8 bond angle is somewhat constrained at 78.19 (5)° whereas the remaining angles are all nearly 90°.

The bond distances involving Mn1 in compound II lie between 2.129 (2) Å (Mn1—O4) and 2.2061 (19) Å (Mn1—O1) which are normal for Mn^II acetate compounds of this type (Dave et al., 1993 and Ciunik & Głowiak, 1980). The long bond distance is to the oxygen originating from the bridging 2MePNO and is 0.0398 Å longer than the Mn1—O1 PNO bond in I but similar to those reported previously (Sniekers et al., 2017; Mondal et al., 2012). The bond angles are within 5° of the expected 90° for octahedral systems with the most constrained angle being O1—Mn1—O2 [85.03 (7)°]. Mn2 has its shortest bond distance to O6 (a μ₂-1,3-acetate bridging from Mn3) of 2.136 (2) Å, whereas its longest distance is 2.239 (2) Å to O10, the terminal water molecule. The μ₂-1,1-2MePNO (O1) bond distance to Mn2 is also long [2.2300 (18) Å]. The μ₃-1,3,3-acetate also links Mn2 and Mn3 via the O3 atom. The O5—Mn2—O10 bond angle is significantly distorted with a value of 81.63 (8)° as is the O6—Mn2—O10 bond angle of 78.61 (8)°. The μ₃-1,3,3-acetate oxygen (O3) forms a long bond with Mn3 as well, observed at 2.3091 (18) Å. The other Mn3—O bond distances are unremarkable at approximately 2.15 Å. The bond angles around Mn3 are all within 4° of 90° in the six-coordinate Mn3 environment.

In compound III, the Mn1—O1 (4MePNO) bond length is the longest of those in this study, with the metal center at 2.203 (3) Å (Sniekers et al., 2017; Mondal et al., 2012) whereas the acetate Mn1—O bond distances range from 2.134 (3) Å to 2.179 (2) Å. The bond angles around the metal center are all within 5° of 90°, with the acetate O—Mn1—O angles being slightly larger, whereas the O(acetate)—Mn1—O(4MePNO) angles are slightly compressed. [For similar compounds, see for example Ciunik & Głowiak (1980) and Dave et al. (1993).] The water is in the lattice and forms a hydrogen bond at 2.21 (2) Å with an O2 atom belonging to one of the acetate μ₂-1,3 acetate bridges.

3. Supramolecular features

The packing of I forms a polymeric structure bisecting the a axis and b axis. Because of the complexity of the structure, many of the details were outlined above. The structure is not linear but forms a zigzag chain in which the bridging acetates and N-oxide ligands connect the Mn ions. There is no evidence for π stacking but interpolymeric chain hydrogen bonding is present.

Compound II forms a similar polymeric structure to I, with the chain bisecting the unit cell at (½, 0, 1) and (½, 1, 0). The chain sets up in a similar fashion as I; however, μ₂-1,3 and μ₃-1,3,3 are the bridges observed while the μ₂-1,1 bridge noted in I is absent.

Compound III forms a polymeric chain which is observed in the b-axis direction. Each manganese(II) atom is bridged by a single 4MePNO and two μ₂-1,3 acetate ions. The 4MePNO bridging ligands are alternating up and down in the a-axis direction. There is no evidence for π stacking due to the long distance found in the structure with the aromatic rings at separations of 7.334 (6) Å.

4. Database survey

A search in the Cambridge Structural Database (CSD Version 5.39, November 2017 update; Groom et al., 2016 ) for aromatic N-oxides and acetate ligands bound to manganese returned 36 entries. Seven of the entries contain derivatives of picolinic N-oxides, thirteen involve derivatives of dipyridal N-oxide and fifteen include di- or tri-acetate ligands. Similar N-oxides with simple benzoate in the list include pyridine N-oxide (YIYRAA; Sarma et al., 2008), and the p-nitrobenzoate with PNO (TIXKER01 and TIXKER; Sarma et al., 2008). Another report by Sarma and co-workers includes the p-hydroxy, o-nitro and p-chlorobenzoate derivatives with PNO (POYRAX; Sarma et al., 2009).

5. Synthesis and crystallization

The manganese(II) coordination polymers were all synthesized by a similar method. 0.245 g (1.00 mmol) manganese(II) acetate tetrahydrate (MnAc₂·4H₂O, FW 245 g mol⁻¹) was dissolved in a minimal amount (20 mL) of methanol. 2 molar equivalents of the appropriate N-oxide (0.191 g pyridine N-oxide, PNO; 0.220 g 2-methylpyrdine N-oxide, 2MePNO; 0.220 g 4-methylpyridine N-oxide, 4MePNO) were similarly dissolved in 10 mL of methanol. The N-oxide alcoholic solution was added in one portion to the Mn^II one. The combined reaction mixture was stirred for 30 minutes, filtered and the filtrate was allowed to evaporate by slow diffusion. X-ray quality crystals were obtained by precipitation from the mother liquor. A final wash with a minimal amount of methanol was performed to assist with removal of excess N-oxide.

Compound I. Yield 0.0642 g, 27.0 (%), decomposition/melting temperature = 433–437 K (turns to a brown liquid). Selected IR bands (ATR, FT–IR, KBr composite, cm⁻¹): 3356 (2, br), 3118 (w), 1558 (s), 1495 (m), 1477 (m), 1418 (m), 1424 (m), 1216 (m), 1025 (w), 835 (m), 783 (m), 653 (w).

Compound II. Yield 0.0484 g, 20.4 (%), decomposition/melting temperature. 417–423 K (turns to a brown liquid). Selected IR bands (ATR, FT–IR, KBr composite, cm⁻¹): 3348 (m, br), 1558 (s), 1495 (m), 1417 (s), 1209 (m), 846 (m), 783 (s), 655 (s).

Compound III. Yield 0.0892 g, 29.7 (%), decomposition/melting temperature. 405–411 K (turns to a black liquid). Selected IR bands (ATR, FT–IR, KBr composite, cm⁻¹): 3412 (m, br), 1652 (w), 1574 (s), 1491 (s), 1424 (m), 1213 (s), 833 (m), 763 (s), 668 (s).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4. All carbon-bound H atoms were positioned geometrically and refined as riding, with C—H = 0.95 or 0.98 Å and U_iso(H) = 1.2U_eq(C) or U_iso(H) = 1.5U_eq(C) for C(H) and CH₃ groups, respectively. In order to ensure chemically meaningful O—H distances for the bound water molecules in the compounds, the oxygen-to-hydrogen distances were restrained to a target value of 0.84 (2) Å (using a DFIX command in SHELXL2017; Sheldrick, 2015b ) and U_iso(H) = 1.5U_eq(O).

Table 4
Experimental details

	I	II	III
Crystal data
Chemical formula	[Mn₄(C₂H₃O₂)₈(C₅H₅NO)₂(H₂O)₂]	[Mn₄(C₂H₃O₂)₈(C₆H₇NO)₂(H₂O)₂]	[Mn(C₂H₃O₂)₂(C₆H₇NO)]·H₂O
M_r	918.34	946.40	300.17
Crystal system, space group	Monoclinic, C2/c	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/n
Temperature (K)	173	173	173
a, b, c (Å)	19.936 (7), 10.603 (4), 18.692 (7)	9.7704 (3), 10.5882 (7), 11.4720 (2)	11.100 (3), 7.334 (3), 15.9808 (4)
α, β, γ (°)	90, 105.925 (4), 90	65.76 (2), 83.84 (2), 65.512 (15)	90, 96.500 (11), 90
V (Å³)	3800 (2)	982.0 (2)	1292.6 (6)
Z	4	1	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	1.38	1.34	1.04
Crystal size (mm)	0.4 × 0.4 × 0.2	0.3 × 0.3 × 0.2	0.2 × 0.05 × 0.05

Data collection
Diffractometer	Rigaku XtaLAB mini	Rigaku XtaLAB mini	Rigaku XtaLAB mini
Absorption correction	Multi-scan (REQAB; Rigaku, 1998 )	Multi-scan (REQAB; Rigaku, 1998)	Multi-scan (REQAB; Rigaku, 1998)
T_min, T_max	0.885, 1.00	0.842, 1.00	0.850, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	19620, 4332, 3855	10542, 4503, 3551	13236, 2957, 2224
R_int	0.046	0.058	0.074
(sin θ/λ)_max (Å⁻¹)	0.649	0.650	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.083, 1.08	0.041, 0.101, 1.06	0.045, 0.105, 1.07
No. of reflections	4332	4503	2957
No. of parameters	249	259	173
No. of restraints	2	2	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.36	0.62, −0.46	0.35, −0.40
Computer programs: CrystalClear (Rigaku, 2009 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC references: 1864753; 1864752; 1864751

Crystal structure: contains datablocks I, II, III. DOI: https://doi.org/10.1107/S205698901801232X/zl2728sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901801232X/zl2728Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S205698901801232X/zl2728IIsup3.hkl

Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S205698901801232X/zl2728IIIsup4.hkl

checkCIF report

Computing details top

Data collection: CrystalClear (Rigaku, 2009) for (I), (II). Cell refinement: CrystalClear (Rigaku, 2009) for (I), (II). Data reduction: CrystalClear (Rigaku, 2009) for (I), (II). For all structures, program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

catena-Poly[manganese(II)-µ₃-acetato-di-µ₂-acetato-[aquamanganese(II)]-µ₂-acetato-µ-(pyridine N-oxide)-manganese(II)-µ₃-acetato-µ₂-acetato-µ-(pyridine N-oxide)-[aquamanganese(II)]-di-µ₂-acetato] (I) top

Crystal data top

[Mn₄(C₂H₃O₂)₈(C₅H₅NO)₂(H₂O)₂]	F(000) = 1872
M_r = 918.34	D_x = 1.605 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.936 (7) Å	Cell parameters from 5012 reflections
b = 10.603 (4) Å	θ = 2.1–27.5°
c = 18.692 (7) Å	µ = 1.38 mm⁻¹
β = 105.925 (4)°	T = 173 K
V = 3800 (2) Å³	Prism, colorless
Z = 4	0.4 × 0.4 × 0.2 mm

Data collection top

Rigaku XtaLAB mini diffractometer	4332 independent reflections
Radiation source: Sealed Tube	3855 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.046
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
profile data from ω–scans	h = −25→25
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −13→13
T_min = 0.885, T_max = 1.00	l = −24→24
19620 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0348P)² + 3.1638P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.083	(Δ/σ)_max = 0.001
S = 1.08	Δρ_max = 0.31 e Å⁻³
4332 reflections	Δρ_min = −0.36 e Å⁻³
249 parameters	Extinction correction: SHELXL-2018/1 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.00109 (13)
Primary atom site location: dual

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Mn1	0.500000	0.500000	0.500000	0.02291 (11)
O1	0.60564 (7)	0.50006 (13)	0.57232 (8)	0.0254 (3)
C1	0.60680 (13)	0.5206 (2)	0.69567 (13)	0.0368 (5)
H1	0.594602	0.605051	0.687011	0.044*
N1	0.61602 (8)	0.44789 (16)	0.64043 (9)	0.0226 (3)
Mn2	0.68359 (2)	0.53844 (3)	0.51070 (2)	0.01989 (10)
C2	0.61555 (15)	0.4693 (3)	0.76534 (13)	0.0455 (6)
H2	0.609182	0.519044	0.803946	0.055*
O2	0.45997 (7)	0.59052 (14)	0.58476 (8)	0.0290 (3)
O3	0.34900 (7)	0.64803 (13)	0.54422 (8)	0.0251 (3)
C3	0.63378 (13)	0.3441 (2)	0.77773 (13)	0.0398 (6)
H3	0.640102	0.308856	0.824684	0.048*
Mn3	0.750000	0.250000	0.500000	0.02146 (11)
C4	0.64253 (12)	0.2717 (2)	0.71959 (13)	0.0355 (5)
H4	0.654963	0.187201	0.727123	0.043*
O4	0.51209 (8)	0.68135 (14)	0.45732 (9)	0.0319 (3)
O5	0.62046 (8)	0.67838 (14)	0.44529 (8)	0.0287 (3)
C5	0.63271 (11)	0.3254 (2)	0.65014 (12)	0.0280 (4)
H5	0.637647	0.276949	0.610427	0.034*
C6	0.41374 (10)	0.67368 (19)	0.57075 (11)	0.0241 (4)
O6	0.75532 (7)	0.56777 (13)	0.44447 (8)	0.0269 (3)
C7	0.43584 (13)	0.8095 (2)	0.58470 (15)	0.0402 (6)
H7A	0.459117	0.836106	0.548603	0.060*
H7B	0.467028	0.817737	0.633739	0.060*
H7C	0.395451	0.861292	0.580629	0.060*
O7	0.79968 (8)	0.37538 (13)	0.44121 (8)	0.0299 (3)
O8	0.74244 (7)	0.10035 (13)	0.41514 (7)	0.0239 (3)
C8	0.56142 (11)	0.72708 (19)	0.43642 (12)	0.0268 (4)
C9	0.54817 (15)	0.8513 (3)	0.39541 (19)	0.0567 (8)
H9A	0.520255	0.837263	0.345358	0.085*
H9C	0.591852	0.888472	0.394560	0.085*
H9B	0.523979	0.907121	0.420264	0.085*
O9	0.69630 (12)	−0.01467 (16)	0.31454 (10)	0.0552 (6)
C10	0.79817 (10)	0.49193 (19)	0.42916 (11)	0.0235 (4)
O10	0.72800 (9)	0.68131 (14)	0.59148 (9)	0.0324 (3)
H10A	0.7598 (12)	0.645 (3)	0.6246 (13)	0.049*
H10B	0.7398 (15)	0.7520 (19)	0.5805 (16)	0.049*
C11	0.85076 (14)	0.5440 (2)	0.39252 (16)	0.0435 (6)
H11A	0.833091	0.536035	0.339502	0.065*
H11B	0.893627	0.497746	0.409250	0.065*
H11C	0.859103	0.631314	0.405432	0.065*
C12	0.70807 (11)	0.0878 (2)	0.34617 (11)	0.0286 (4)
C13	0.68183 (13)	0.2058 (2)	0.30226 (12)	0.0362 (5)
H13A	0.691076	0.277449	0.334898	0.054*
H13B	0.632510	0.198775	0.279886	0.054*
H13C	0.705221	0.216242	0.264085	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0195 (2)	0.0200 (2)	0.0295 (2)	0.00260 (15)	0.00725 (17)	0.00445 (17)
O1	0.0230 (7)	0.0277 (8)	0.0258 (7)	0.0009 (6)	0.0073 (5)	0.0085 (6)
C1	0.0477 (14)	0.0283 (12)	0.0336 (12)	0.0043 (10)	0.0098 (10)	−0.0067 (9)
N1	0.0228 (8)	0.0231 (8)	0.0224 (8)	0.0014 (6)	0.0069 (6)	0.0022 (7)
Mn2	0.02113 (16)	0.01489 (16)	0.02513 (17)	0.00127 (10)	0.00883 (12)	0.00102 (11)
C2	0.0627 (17)	0.0480 (15)	0.0268 (12)	0.0038 (13)	0.0141 (11)	−0.0095 (11)
O2	0.0275 (8)	0.0293 (8)	0.0305 (8)	0.0055 (6)	0.0082 (6)	0.0002 (6)
O3	0.0239 (7)	0.0178 (7)	0.0331 (8)	0.0015 (5)	0.0070 (6)	−0.0026 (6)
C3	0.0437 (14)	0.0487 (15)	0.0263 (11)	0.0020 (11)	0.0087 (10)	0.0076 (10)
Mn3	0.0249 (2)	0.0140 (2)	0.0275 (2)	0.00299 (15)	0.01058 (17)	0.00005 (16)
C4	0.0398 (13)	0.0320 (12)	0.0347 (12)	0.0047 (10)	0.0102 (10)	0.0081 (10)
O4	0.0289 (8)	0.0233 (7)	0.0466 (9)	0.0034 (6)	0.0155 (7)	0.0078 (7)
O5	0.0283 (8)	0.0244 (7)	0.0350 (8)	0.0064 (6)	0.0113 (6)	0.0075 (6)
C5	0.0318 (11)	0.0255 (10)	0.0288 (10)	0.0044 (8)	0.0117 (8)	0.0026 (8)
C6	0.0266 (10)	0.0215 (10)	0.0257 (10)	−0.0009 (8)	0.0095 (8)	−0.0011 (8)
O6	0.0292 (8)	0.0204 (7)	0.0361 (8)	0.0031 (6)	0.0173 (6)	0.0035 (6)
C7	0.0323 (12)	0.0270 (12)	0.0611 (16)	−0.0051 (9)	0.0124 (11)	−0.0075 (11)
O7	0.0394 (9)	0.0180 (7)	0.0390 (8)	0.0044 (6)	0.0218 (7)	0.0033 (6)
O8	0.0282 (7)	0.0188 (7)	0.0248 (7)	0.0045 (5)	0.0072 (6)	0.0000 (5)
C8	0.0285 (11)	0.0204 (10)	0.0325 (11)	0.0026 (8)	0.0101 (8)	0.0039 (8)
C9	0.0467 (16)	0.0354 (14)	0.096 (2)	0.0137 (12)	0.0331 (15)	0.0358 (15)
O9	0.0897 (16)	0.0254 (9)	0.0329 (9)	0.0061 (9)	−0.0127 (9)	−0.0053 (7)
C10	0.0256 (10)	0.0221 (10)	0.0251 (10)	0.0022 (8)	0.0107 (8)	0.0017 (8)
O10	0.0397 (9)	0.0176 (7)	0.0364 (9)	−0.0023 (6)	0.0045 (7)	−0.0003 (6)
C11	0.0506 (15)	0.0286 (12)	0.0652 (17)	0.0046 (10)	0.0394 (13)	0.0088 (11)
C12	0.0334 (11)	0.0239 (10)	0.0262 (10)	0.0025 (8)	0.0042 (8)	−0.0014 (8)
C13	0.0454 (13)	0.0314 (12)	0.0294 (11)	0.0092 (10)	0.0062 (10)	0.0042 (9)

Geometric parameters (Å, º) top

Mn1—O1ⁱ	2.1680 (15)	C4—H4	0.9300
Mn1—O1	2.1681 (15)	C4—C5	1.381 (3)
Mn1—O2ⁱ	2.1822 (15)	O4—C8	1.251 (3)
Mn1—O2	2.1822 (15)	O5—C8	1.254 (2)
Mn1—O4ⁱ	2.1207 (16)	C5—H5	0.9300
Mn1—O4	2.1207 (16)	C6—C7	1.508 (3)
O1—N1	1.351 (2)	O6—C10	1.262 (2)
O1—Mn2	2.2113 (15)	C7—H7A	0.9600
C1—H1	0.9300	C7—H7B	0.9600
C1—N1	1.341 (3)	C7—H7C	0.9600
C1—C2	1.377 (3)	O7—C10	1.255 (2)
N1—C5	1.341 (3)	O8—C12	1.290 (2)
Mn2—O3ⁱ	2.2404 (15)	C8—C9	1.510 (3)
Mn2—O5	2.1062 (15)	C9—H9A	0.9600
Mn2—O6	2.1551 (15)	C9—H9C	0.9600
Mn2—O8ⁱⁱ	2.2671 (14)	C9—H9B	0.9600
Mn2—O10	2.1506 (16)	O9—C12	1.228 (3)
C2—H2	0.9300	C10—C11	1.506 (3)
C2—C3	1.380 (4)	O10—H10A	0.848 (17)
O2—C6	1.250 (2)	O10—H10B	0.829 (17)
O3—Mn3ⁱⁱⁱ	2.2028 (15)	C11—H11A	0.9600
O3—C6	1.278 (2)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C3—C4	1.380 (3)	C12—C13	1.509 (3)
Mn3—O7ⁱⁱ	2.1338 (15)	C13—H13A	0.9600
Mn3—O7	2.1338 (15)	C13—H13B	0.9600
Mn3—O8	2.2194 (14)	C13—H13C	0.9600
Mn3—O8ⁱⁱ	2.2194 (14)

O1ⁱ—Mn1—O1	180.00 (7)	O7—Mn3—O7ⁱⁱ	180.0
O1ⁱ—Mn1—O2ⁱ	91.91 (6)	O7—Mn3—O8	91.58 (6)
O1—Mn1—O2ⁱ	88.09 (6)	O7—Mn3—O8ⁱⁱ	88.43 (6)
O1ⁱ—Mn1—O2	88.09 (6)	O7ⁱⁱ—Mn3—O8ⁱⁱ	91.57 (6)
O1—Mn1—O2	91.91 (6)	O7ⁱⁱ—Mn3—O8	88.43 (6)
O2—Mn1—O2ⁱ	180.0	O8—Mn3—O8ⁱⁱ	180.00 (5)
O4ⁱ—Mn1—O1ⁱ	92.47 (6)	C3—C4—H4	120.2
O4—Mn1—O1	92.47 (6)	C3—C4—C5	119.7 (2)
O4ⁱ—Mn1—O1	87.53 (6)	C5—C4—H4	120.2
O4—Mn1—O1ⁱ	87.53 (6)	C8—O4—Mn1	130.47 (13)
O4ⁱ—Mn1—O2	91.36 (6)	C8—O5—Mn2	139.17 (14)
O4—Mn1—O2	88.64 (6)	N1—C5—C4	119.5 (2)
O4—Mn1—O2ⁱ	91.36 (6)	N1—C5—H5	120.2
O4ⁱ—Mn1—O2ⁱ	88.64 (6)	C4—C5—H5	120.2
O4—Mn1—O4ⁱ	180.0	O2—C6—O3	122.61 (19)
Mn1—O1—Mn2	112.12 (6)	O2—C6—C7	118.29 (19)
N1—O1—Mn1	117.31 (11)	O3—C6—C7	119.09 (18)
N1—O1—Mn2	128.21 (11)	C10—O6—Mn2	129.45 (13)
N1—C1—H1	120.3	C6—C7—H7A	109.5
N1—C1—C2	119.5 (2)	C6—C7—H7B	109.5
C2—C1—H1	120.3	C6—C7—H7C	109.5
C1—N1—O1	118.17 (18)	H7A—C7—H7B	109.5
C5—N1—O1	119.51 (16)	H7A—C7—H7C	109.5
C5—N1—C1	122.28 (19)	H7B—C7—H7C	109.5
O1—Mn2—O3ⁱ	85.37 (6)	C10—O7—Mn3	135.59 (13)
O1—Mn2—O8ⁱⁱ	89.66 (5)	Mn3—O8—Mn2ⁱⁱ	97.00 (6)
O3ⁱ—Mn2—O8ⁱⁱ	76.44 (5)	C12—O8—Mn2ⁱⁱ	128.45 (13)
O5—Mn2—O1	92.21 (6)	C12—O8—Mn3	134.54 (13)
O5—Mn2—O3ⁱ	107.68 (6)	O4—C8—O5	126.06 (19)
O5—Mn2—O6	87.13 (6)	O4—C8—C9	116.96 (19)
O5—Mn2—O8ⁱⁱ	175.59 (6)	O5—C8—C9	116.97 (19)
O5—Mn2—O10	88.66 (6)	C8—C9—H9A	109.5
O6—Mn2—O1	176.02 (6)	C8—C9—H9C	109.5
O6—Mn2—O3ⁱ	91.08 (6)	C8—C9—H9B	109.5
O6—Mn2—O8ⁱⁱ	91.27 (6)	H9A—C9—H9C	109.5
O10—Mn2—O1	88.66 (6)	H9A—C9—H9B	109.5
O10—Mn2—O3ⁱ	162.77 (6)	H9C—C9—H9B	109.5
O10—Mn2—O6	95.25 (6)	O6—C10—C11	117.96 (18)
O10—Mn2—O8ⁱⁱ	87.39 (6)	O7—C10—O6	124.82 (19)
C1—C2—H2	120.1	O7—C10—C11	117.21 (18)
C1—C2—C3	119.9 (2)	Mn2—O10—H10A	106 (2)
C3—C2—H2	120.1	Mn2—O10—H10B	124 (2)
C6—O2—Mn1	123.62 (13)	H10A—O10—H10B	113 (3)
Mn3ⁱⁱⁱ—O3—Mn2ⁱ	98.27 (6)	C10—C11—H11A	109.5
C6—O3—Mn2ⁱ	120.04 (12)	C10—C11—H11B	109.5
C6—O3—Mn3ⁱⁱⁱ	138.28 (13)	C10—C11—H11C	109.5
C2—C3—H3	120.4	H11A—C11—H11B	109.5
C2—C3—C4	119.2 (2)	H11A—C11—H11C	109.5
C4—C3—H3	120.4	H11B—C11—H11C	109.5
O3ⁱ—Mn3—O3^iv	180.00 (7)	O8—C12—C13	117.86 (18)
O3ⁱ—Mn3—O8ⁱⁱ	78.19 (5)	O9—C12—O8	123.5 (2)
O3^iv—Mn3—O8ⁱⁱ	101.81 (5)	O9—C12—C13	118.66 (19)
O3^iv—Mn3—O8	78.19 (5)	C12—C13—H13A	109.5
O3ⁱ—Mn3—O8	101.81 (5)	C12—C13—H13B	109.5
O7—Mn3—O3ⁱ	89.75 (6)	C12—C13—H13C	109.5
O7ⁱⁱ—Mn3—O3^iv	89.75 (6)	H13A—C13—H13B	109.5
O7ⁱⁱ—Mn3—O3ⁱ	90.25 (6)	H13A—C13—H13C	109.5
O7—Mn3—O3^iv	90.25 (6)	H13B—C13—H13C	109.5

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, −y+1/2, −z+1; (iii) x−1/2, y+1/2, z; (iv) x+1/2, y−1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···O9ⁱⁱ	0.85 (2)	1.85 (2)	2.652 (2)	157 (3)
O10—H10B···O6^v	0.83 (2)	1.98 (2)	2.786 (2)	166 (3)

Symmetry codes: (ii) −x+3/2, −y+1/2, −z+1; (v) −x+3/2, −y+3/2, −z+1.

catena-Poly[[manganese(II)]-µ₃-acetato-µ₂-acetato-µ-(2-methylpyridine N-oxide)-[aquamanganese(II)]-di-µ₂-acetato-manganese(II)-di-µ₂-acetato-µ₃-acetato-[aquamanganese(II)]-µ₂-acetato-µ-(2-methylpyridine N-oxide)] (II) top

Crystal data top

[Mn₄(C₂H₃O₂)₈(C₆H₇NO)₂(H₂O)₂]	Z = 1
M_r = 946.4	F(000) = 484
Triclinic, P1	D_x = 1.600 Mg m⁻³
a = 9.7704 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5882 (7) Å	Cell parameters from 2512 reflections
c = 11.4720 (2) Å	θ = 2.0–27.5°
α = 65.76 (2)°	µ = 1.34 mm⁻¹
β = 83.84 (2)°	T = 173 K
γ = 65.512 (15)°	Prism, colorless
V = 982.0 (2) Å³	0.3 × 0.3 × 0.2 mm

Data collection top

Rigaku XtaLAB mini diffractometer	4503 independent reflections
Radiation source: Sealed Tube	3551 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.058
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.3°
profile data from ω–scans	h = −12→12
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −13→13
T_min = 0.842, T_max = 1.00	l = −14→14
10542 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.0271P)² + 0.5206P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.101	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.62 e Å⁻³
4503 reflections	Δρ_min = −0.46 e Å⁻³
259 parameters	Extinction correction: SHELXL-2018/1 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0045 (10)
Primary atom site location: dual

Special details top

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

	x	y	z	U_iso*/U_eq
Mn1	0.500000	0.500000	0.500000	0.02633 (15)
C1	0.9223 (3)	0.1967 (3)	0.5954 (3)	0.0385 (7)
O1	0.66323 (19)	0.2610 (2)	0.58767 (17)	0.0294 (4)
N1	0.7920 (3)	0.2213 (2)	0.6544 (2)	0.0306 (5)
C2	1.0513 (4)	0.1617 (4)	0.6641 (4)	0.0526 (9)
H2	1.143547	0.147895	0.624004	0.063*
O2	0.6422 (2)	0.5705 (2)	0.35280 (18)	0.0405 (5)
Mn2	0.54423 (4)	0.10659 (4)	0.65107 (4)	0.02574 (12)
C3	1.0472 (4)	0.1465 (4)	0.7900 (4)	0.0559 (9)
H3	1.135892	0.121710	0.836731	0.067*
O3	0.5590 (2)	0.80401 (19)	0.20131 (16)	0.0292 (4)
Mn3	0.500000	0.000000	1.000000	0.02716 (15)
C4	0.9121 (4)	0.1680 (4)	0.8465 (3)	0.0446 (8)
H4	0.907481	0.155806	0.933430	0.053*
O4	0.3972 (3)	0.4521 (2)	0.37791 (19)	0.0434 (5)
O5	0.3654 (2)	0.2403 (2)	0.49693 (19)	0.0389 (5)
C5	0.7842 (4)	0.2072 (3)	0.7767 (3)	0.0375 (7)
H5	0.690486	0.224241	0.814678	0.045*
C6	0.9159 (4)	0.2095 (4)	0.4616 (3)	0.0518 (9)
H6A	0.866513	0.147157	0.458109	0.078*
H6B	1.018458	0.174165	0.434390	0.078*
H6C	0.858321	0.315728	0.404389	0.078*
O6	0.7494 (2)	−0.0675 (2)	0.76008 (18)	0.0411 (5)
C7	0.6334 (3)	0.6596 (3)	0.2404 (2)	0.0292 (6)
O7	0.7340 (2)	−0.0951 (2)	0.96318 (18)	0.0391 (5)
O8	0.4469 (2)	−0.0610 (2)	0.72192 (18)	0.0381 (5)
C8	0.7129 (5)	0.5940 (4)	0.1464 (3)	0.0695 (13)
H8A	0.651688	0.650930	0.064547	0.104*
H8C	0.728199	0.487456	0.179635	0.104*
H8B	0.810839	0.600750	0.133554	0.104*
O9	0.4385 (3)	−0.1325 (2)	0.93300 (18)	0.0417 (5)
C9	0.3347 (4)	0.3642 (3)	0.4000 (3)	0.0388 (7)
C10	0.2131 (5)	0.4060 (4)	0.3031 (4)	0.0752 (13)
H10A	0.227713	0.316316	0.288714	0.113*
H10B	0.218744	0.485502	0.222086	0.113*
H10C	0.113896	0.443323	0.335646	0.113*
O10	0.6635 (2)	0.0116 (2)	0.50856 (19)	0.0347 (5)
H10D	0.669 (4)	−0.076 (2)	0.529 (3)	0.052*
H10E	0.615 (4)	0.054 (4)	0.436 (2)	0.052*
C11	0.8010 (3)	−0.1286 (3)	0.8738 (3)	0.0324 (6)
C12	0.9586 (4)	−0.2532 (5)	0.9039 (3)	0.0574 (10)
H12B	1.028728	−0.212929	0.850872	0.086*
H12C	0.959934	−0.336348	0.885672	0.086*
H12A	0.989418	−0.291080	0.994697	0.086*
C13	0.4250 (3)	−0.1437 (3)	0.8312 (3)	0.0299 (6)
C14	0.3769 (5)	−0.2656 (4)	0.8398 (3)	0.0583 (10)
H14A	0.291205	−0.220931	0.777399	0.087*
H14C	0.347239	−0.310285	0.926417	0.087*
H14B	0.461132	−0.344649	0.821308	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0309 (3)	0.0219 (3)	0.0235 (3)	−0.0121 (2)	−0.0010 (2)	−0.0047 (2)
C1	0.0297 (15)	0.0323 (15)	0.0463 (17)	−0.0089 (13)	0.0010 (13)	−0.0126 (14)
O1	0.0254 (9)	0.0257 (9)	0.0335 (10)	−0.0095 (8)	−0.0038 (8)	−0.0082 (8)
N1	0.0301 (12)	0.0259 (11)	0.0320 (12)	−0.0113 (10)	−0.0046 (10)	−0.0066 (10)
C2	0.0262 (15)	0.058 (2)	0.064 (2)	−0.0109 (15)	−0.0015 (15)	−0.0215 (19)
O2	0.0388 (11)	0.0326 (11)	0.0319 (11)	−0.0104 (9)	0.0061 (9)	−0.0015 (9)
Mn2	0.0309 (2)	0.0255 (2)	0.0225 (2)	−0.01314 (18)	0.00076 (16)	−0.00934 (17)
C3	0.0438 (19)	0.054 (2)	0.065 (2)	−0.0127 (17)	−0.0211 (17)	−0.0211 (19)
O3	0.0372 (10)	0.0228 (9)	0.0237 (9)	−0.0106 (8)	0.0045 (8)	−0.0081 (8)
Mn3	0.0340 (3)	0.0254 (3)	0.0215 (3)	−0.0123 (2)	0.0022 (2)	−0.0089 (2)
C4	0.0488 (19)	0.0428 (18)	0.0398 (17)	−0.0160 (16)	−0.0093 (15)	−0.0144 (15)
O4	0.0600 (14)	0.0399 (12)	0.0350 (11)	−0.0272 (11)	−0.0071 (10)	−0.0100 (10)
O5	0.0449 (12)	0.0278 (10)	0.0385 (11)	−0.0133 (9)	−0.0110 (9)	−0.0065 (9)
C5	0.0430 (17)	0.0346 (16)	0.0351 (15)	−0.0177 (14)	0.0004 (13)	−0.0118 (13)
C6	0.0410 (18)	0.060 (2)	0.0445 (19)	−0.0117 (17)	0.0085 (15)	−0.0222 (18)
O6	0.0430 (12)	0.0371 (11)	0.0324 (11)	−0.0075 (10)	−0.0079 (9)	−0.0105 (9)
C7	0.0300 (14)	0.0264 (13)	0.0290 (14)	−0.0124 (11)	0.0060 (11)	−0.0092 (11)
O7	0.0366 (11)	0.0430 (12)	0.0334 (11)	−0.0120 (10)	0.0040 (9)	−0.0162 (10)
O8	0.0544 (13)	0.0426 (12)	0.0298 (10)	−0.0322 (11)	0.0046 (9)	−0.0139 (9)
C8	0.109 (3)	0.0298 (17)	0.041 (2)	−0.006 (2)	0.019 (2)	−0.0141 (16)
O9	0.0666 (15)	0.0410 (12)	0.0278 (10)	−0.0306 (11)	0.0047 (10)	−0.0149 (10)
C9	0.0446 (17)	0.0289 (15)	0.0403 (16)	−0.0114 (13)	−0.0100 (14)	−0.0121 (13)
C10	0.090 (3)	0.047 (2)	0.077 (3)	−0.030 (2)	−0.052 (2)	0.001 (2)
O10	0.0417 (11)	0.0367 (11)	0.0298 (10)	−0.0172 (10)	0.0012 (9)	−0.0158 (10)
C11	0.0308 (14)	0.0283 (14)	0.0371 (15)	−0.0113 (12)	−0.0021 (12)	−0.0120 (13)
C12	0.0366 (18)	0.066 (2)	0.051 (2)	0.0004 (17)	−0.0074 (16)	−0.0263 (19)
C13	0.0335 (14)	0.0277 (14)	0.0294 (14)	−0.0152 (12)	0.0017 (11)	−0.0094 (12)
C14	0.096 (3)	0.062 (2)	0.048 (2)	−0.061 (2)	0.019 (2)	−0.0251 (18)

Geometric parameters (Å, º) top

Mn1—O1	2.2061 (19)	C4—C5	1.374 (4)
Mn1—O1ⁱ	2.2061 (19)	O4—C9	1.244 (4)
Mn1—O2ⁱ	2.159 (2)	O5—C9	1.263 (3)
Mn1—O2	2.159 (2)	C5—H5	0.9500
Mn1—O4	2.129 (2)	C6—H6A	0.9800
Mn1—O4ⁱ	2.129 (2)	C6—H6B	0.9800
C1—N1	1.354 (4)	C6—H6C	0.9800
C1—C2	1.389 (4)	O6—C11	1.246 (3)
C1—C6	1.491 (4)	C7—C8	1.495 (4)
O1—N1	1.359 (3)	O7—C11	1.253 (3)
O1—Mn2	2.2300 (18)	O8—C13	1.258 (3)
N1—C5	1.346 (4)	C8—H8A	0.9800
C2—H2	0.9500	C8—H8C	0.9800
C2—C3	1.385 (5)	C8—H8B	0.9800
O2—C7	1.232 (3)	O9—C13	1.247 (3)
Mn2—O3ⁱ	2.2224 (18)	C9—C10	1.513 (4)
Mn2—O5	2.177 (2)	C10—H10A	0.9800
Mn2—O6	2.136 (2)	C10—H10B	0.9800
Mn2—O8	2.182 (2)	C10—H10C	0.9800
Mn2—O10	2.239 (2)	O10—H10D	0.838 (18)
C3—H3	0.9500	O10—H10E	0.846 (18)
C3—C4	1.379 (5)	C11—C12	1.513 (4)
O3—Mn3ⁱⁱ	2.3091 (18)	C12—H12B	0.9800
O3—C7	1.286 (3)	C12—H12C	0.9800
Mn3—O7ⁱⁱⁱ	2.157 (2)	C12—H12A	0.9800
Mn3—O7	2.157 (2)	C13—C14	1.511 (4)
Mn3—O9	2.1453 (19)	C14—H14A	0.9800
Mn3—O9ⁱⁱⁱ	2.1452 (19)	C14—H14C	0.9800
C4—H4	0.9500	C14—H14B	0.9800

O1ⁱ—Mn1—O1	180.0	O9—Mn3—O7	93.91 (8)
O2ⁱ—Mn1—O1	85.03 (7)	O9ⁱⁱⁱ—Mn3—O7ⁱⁱⁱ	93.91 (8)
O2—Mn1—O1ⁱ	85.03 (7)	O9ⁱⁱⁱ—Mn3—O9	180.0
O2—Mn1—O1	94.97 (7)	C3—C4—H4	120.1
O2ⁱ—Mn1—O1ⁱ	94.97 (7)	C5—C4—C3	119.8 (3)
O2—Mn1—O2ⁱ	180.0	C5—C4—H4	120.1
O4ⁱ—Mn1—O1ⁱ	91.37 (8)	C9—O4—Mn1	132.59 (19)
O4—Mn1—O1	91.37 (8)	C9—O5—Mn2	133.4 (2)
O4—Mn1—O1ⁱ	88.63 (8)	N1—C5—C4	119.8 (3)
O4ⁱ—Mn1—O1	88.63 (8)	N1—C5—H5	120.1
O4ⁱ—Mn1—O2ⁱ	91.45 (8)	C4—C5—H5	120.1
O4ⁱ—Mn1—O2	88.55 (8)	C1—C6—H6A	109.5
O4—Mn1—O2	91.45 (8)	C1—C6—H6B	109.5
O4—Mn1—O2ⁱ	88.55 (8)	C1—C6—H6C	109.5
O4—Mn1—O4ⁱ	180.0	H6A—C6—H6B	109.5
N1—C1—C2	117.6 (3)	H6A—C6—H6C	109.5
N1—C1—C6	117.2 (3)	H6B—C6—H6C	109.5
C2—C1—C6	125.2 (3)	C11—O6—Mn2	136.82 (19)
Mn1—O1—Mn2	110.48 (7)	O2—C7—O3	123.2 (2)
N1—O1—Mn1	120.93 (14)	O2—C7—C8	117.5 (2)
N1—O1—Mn2	119.74 (14)	O3—C7—C8	119.4 (2)
C1—N1—O1	118.8 (2)	C11—O7—Mn3	134.16 (18)
C5—N1—C1	122.8 (3)	C13—O8—Mn2	134.65 (18)
C5—N1—O1	118.4 (2)	C7—C8—H8A	109.5
C1—C2—H2	119.5	C7—C8—H8C	109.5
C3—C2—C1	121.0 (3)	C7—C8—H8B	109.5
C3—C2—H2	119.5	H8A—C8—H8C	109.5
C7—O2—Mn1	140.53 (19)	H8A—C8—H8B	109.5
O1—Mn2—O10	88.73 (7)	H8C—C8—H8B	109.5
O3ⁱ—Mn2—O1	89.31 (7)	C13—O9—Mn3	139.90 (18)
O3ⁱ—Mn2—O10	176.15 (7)	O4—C9—O5	125.4 (3)
O5—Mn2—O1	97.41 (7)	O4—C9—C10	118.2 (3)
O5—Mn2—O3ⁱ	101.91 (7)	O5—C9—C10	116.4 (3)
O5—Mn2—O8	87.26 (8)	C9—C10—H10A	109.5
O5—Mn2—O10	81.63 (8)	C9—C10—H10B	109.5
O6—Mn2—O1	86.79 (8)	C9—C10—H10C	109.5
O6—Mn2—O3ⁱ	97.97 (7)	H10A—C10—H10B	109.5
O6—Mn2—O5	159.71 (8)	H10A—C10—H10C	109.5
O6—Mn2—O8	88.10 (8)	H10B—C10—H10C	109.5
O6—Mn2—O10	78.61 (8)	Mn2—O10—H10D	112 (2)
O8—Mn2—O1	174.87 (7)	Mn2—O10—H10E	115 (2)
O8—Mn2—O3ⁱ	91.81 (7)	H10D—O10—H10E	99 (3)
O8—Mn2—O10	89.86 (8)	O6—C11—O7	125.7 (3)
C2—C3—H3	120.6	O6—C11—C12	116.1 (3)
C4—C3—C2	118.8 (3)	O7—C11—C12	118.3 (3)
C4—C3—H3	120.6	C11—C12—H12B	109.5
Mn2ⁱ—O3—Mn3ⁱⁱ	110.16 (7)	C11—C12—H12C	109.5
C7—O3—Mn2ⁱ	117.09 (16)	C11—C12—H12A	109.5
C7—O3—Mn3ⁱⁱ	132.72 (17)	H12B—C12—H12C	109.5
O3^iv—Mn3—O3ⁱ	180.0	H12B—C12—H12A	109.5
O7ⁱⁱⁱ—Mn3—O3ⁱ	88.03 (7)	H12C—C12—H12A	109.5
O7—Mn3—O3^iv	88.03 (7)	O8—C13—C14	117.4 (2)
O7—Mn3—O3ⁱ	91.97 (7)	O9—C13—O8	125.2 (3)
O7ⁱⁱⁱ—Mn3—O3^iv	91.97 (7)	O9—C13—C14	117.3 (2)
O7—Mn3—O7ⁱⁱⁱ	180.0	C13—C14—H14A	109.5
O9ⁱⁱⁱ—Mn3—O3ⁱ	88.85 (7)	C13—C14—H14C	109.5
O9ⁱⁱⁱ—Mn3—O3^iv	91.15 (7)	C13—C14—H14B	109.5
O9—Mn3—O3^iv	88.85 (7)	H14A—C14—H14C	109.5
O9—Mn3—O3ⁱ	91.15 (7)	H14A—C14—H14B	109.5
O9ⁱⁱⁱ—Mn3—O7	86.09 (8)	H14C—C14—H14B	109.5
O9—Mn3—O7ⁱⁱⁱ	86.09 (8)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z−1; (iii) −x+1, −y, −z+2; (iv) x, y−1, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10D···O5^v	0.84 (2)	2.04 (2)	2.821 (3)	155 (3)
O10—H10E···O8^v	0.85 (2)	1.94 (2)	2.727 (3)	155 (3)

Symmetry code: (v) −x+1, −y, −z+1.

catena-Poly[[manganese(II)-di-µ₂-acetato-µ-(4-methylpyridine N-oxide)] monohydrate] (III) top

Crystal data top

[Mn(C₂H₃O₂)₂(C₆H₇NO)]·H₂O	F(000) = 620
M_r = 300.17	D_x = 1.542 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.100 (3) Å	Cell parameters from 2982 reflections
b = 7.334 (3) Å	θ = 2.1–27.5°
c = 15.9808 (4) Å	µ = 1.04 mm⁻¹
β = 96.500 (11)°	T = 173 K
V = 1292.6 (6) Å³	Prism, colorless
Z = 4	0.2 × 0.05 × 0.05 mm

Data collection top

Rigaku XtaLAB mini diffractometer	2224 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	R_int = 0.074
profile data from ω–scans	θ_max = 27.6°, θ_min = 2.1°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −14→14
T_min = 0.850, T_max = 1.00	k = −9→9
13236 measured reflections	l = −20→20
2957 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.0269P)² + 1.0998P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.105	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 0.35 e Å⁻³
2957 reflections	Δρ_min = −0.40 e Å⁻³
173 parameters	Extinction correction: SHELXL-2018/1 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0042 (9)

Special details top

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

	x	y	z	U_iso*/U_eq
Mn1	0.25529 (4)	0.54319 (6)	0.75049 (3)	0.02337 (15)
O1	0.35635 (15)	0.7980 (2)	0.73689 (12)	0.0243 (4)
C1	0.5439 (2)	0.8534 (4)	0.69051 (19)	0.0316 (7)
H1	0.505841	0.869094	0.636076	0.038*
N1	0.47864 (19)	0.8127 (3)	0.75356 (14)	0.0235 (5)
C2	0.6685 (3)	0.8721 (4)	0.7071 (2)	0.0354 (7)
H2	0.713428	0.902878	0.663478	0.042*
O2	0.33022 (19)	0.4486 (3)	0.63859 (13)	0.0372 (5)
O3	0.3188 (2)	0.1450 (3)	0.63793 (13)	0.0389 (5)
C3	0.7278 (2)	0.8459 (4)	0.7874 (2)	0.0323 (7)
C4	0.6557 (3)	0.8040 (4)	0.85053 (19)	0.0321 (7)
H4	0.691779	0.786075	0.905330	0.039*
O4	0.10483 (18)	0.6385 (3)	0.66703 (14)	0.0402 (6)
O5	0.09920 (19)	0.9411 (3)	0.66333 (14)	0.0385 (5)
C5	0.5315 (3)	0.7885 (4)	0.83299 (18)	0.0284 (6)
H5	0.484307	0.761524	0.875895	0.034*
C6	0.8641 (3)	0.8641 (5)	0.8053 (2)	0.0455 (8)
H6A	0.884813	0.903431	0.862398	0.068*
H6B	0.892537	0.952060	0.767630	0.068*
H6C	0.901330	0.748229	0.797218	0.068*
C7	0.3391 (2)	0.2954 (4)	0.60495 (17)	0.0259 (6)
C8	0.3785 (3)	0.2898 (5)	0.51770 (19)	0.0379 (7)
H8A	0.351789	0.398675	0.487760	0.057*
H8B	0.343341	0.185322	0.488106	0.057*
H8C	0.465247	0.282015	0.521701	0.057*
C9	0.0622 (2)	0.7859 (4)	0.63902 (18)	0.0271 (6)
C10	−0.0435 (3)	0.7767 (5)	0.5705 (2)	0.0461 (9)
H10A	−0.083947	0.892610	0.565920	0.069*
H10B	−0.099334	0.684427	0.584238	0.069*
H10C	−0.014279	0.747388	0.517831	0.069*
O6	0.3091 (2)	0.7951 (4)	0.53409 (15)	0.0440 (6)
H6D	0.301 (4)	0.882 (4)	0.567 (2)	0.066*
H6E	0.313 (4)	0.708 (4)	0.568 (2)	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0222 (2)	0.0195 (2)	0.0284 (2)	−0.00149 (16)	0.00291 (17)	−0.00006 (16)
O1	0.0159 (9)	0.0210 (10)	0.0355 (11)	−0.0003 (7)	0.0009 (8)	−0.0011 (8)
C1	0.0253 (14)	0.0377 (18)	0.0317 (16)	−0.0018 (13)	0.0033 (12)	0.0015 (13)
N1	0.0167 (10)	0.0223 (12)	0.0311 (12)	−0.0014 (9)	0.0014 (9)	−0.0015 (10)
C2	0.0279 (15)	0.0411 (19)	0.0388 (17)	−0.0032 (14)	0.0105 (13)	−0.0054 (15)
O2	0.0438 (13)	0.0300 (12)	0.0403 (13)	−0.0022 (10)	0.0155 (10)	−0.0046 (9)
O3	0.0518 (13)	0.0287 (12)	0.0396 (12)	0.0006 (10)	0.0192 (11)	0.0044 (10)
C3	0.0227 (14)	0.0291 (17)	0.0445 (18)	0.0001 (12)	0.0006 (13)	−0.0065 (13)
C4	0.0298 (15)	0.0320 (17)	0.0327 (16)	0.0002 (12)	−0.0047 (13)	−0.0015 (13)
O4	0.0329 (11)	0.0293 (12)	0.0547 (14)	−0.0023 (9)	−0.0114 (10)	0.0081 (10)
O5	0.0343 (12)	0.0250 (12)	0.0529 (14)	0.0027 (9)	−0.0093 (10)	−0.0067 (10)
C5	0.0283 (15)	0.0279 (16)	0.0289 (15)	0.0011 (12)	0.0031 (12)	−0.0002 (12)
C6	0.0270 (16)	0.047 (2)	0.061 (2)	−0.0010 (15)	0.0000 (15)	−0.0082 (18)
C7	0.0215 (13)	0.0306 (16)	0.0259 (14)	0.0000 (11)	0.0036 (11)	−0.0001 (12)
C8	0.0426 (18)	0.0417 (19)	0.0307 (16)	−0.0055 (14)	0.0097 (14)	0.0014 (14)
C9	0.0221 (14)	0.0310 (16)	0.0284 (15)	0.0022 (12)	0.0033 (12)	0.0028 (12)
C10	0.043 (2)	0.043 (2)	0.047 (2)	−0.0048 (16)	−0.0164 (17)	0.0023 (16)
O6	0.0536 (15)	0.0473 (16)	0.0306 (12)	−0.0011 (13)	0.0023 (11)	−0.0039 (10)

Geometric parameters (Å, º) top

Mn1—O1ⁱ	2.206 (2)	C4—C5	1.380 (4)
Mn1—O1	2.203 (2)	O4—C9	1.243 (3)
Mn1—O2	2.170 (2)	O5—C9	1.257 (3)
Mn1—O3ⁱⁱ	2.179 (2)	C5—H5	0.9300
Mn1—O4	2.134 (2)	C6—H6A	0.9600
Mn1—O5ⁱ	2.136 (2)	C6—H6B	0.9600
O1—N1	1.358 (3)	C6—H6C	0.9600
C1—H1	0.9300	C7—C8	1.508 (4)
C1—N1	1.339 (4)	C8—H8A	0.9600
C1—C2	1.386 (4)	C8—H8B	0.9600
N1—C5	1.348 (4)	C8—H8C	0.9600
C2—H2	0.9300	C9—C10	1.513 (4)
C2—C3	1.387 (4)	C10—H10A	0.9600
O2—C7	1.254 (3)	C10—H10B	0.9600
O3—C7	1.254 (3)	C10—H10C	0.9600
C3—C4	1.391 (4)	O6—H6D	0.841 (19)
C3—C6	1.514 (4)	O6—H6E	0.839 (18)
C4—H4	0.9300

O1—Mn1—O1ⁱ	176.46 (6)	C5—C4—C3	120.9 (3)
O2—Mn1—O1ⁱ	94.96 (8)	C5—C4—H4	119.5
O2—Mn1—O1	86.72 (8)	C9—O4—Mn1	138.5 (2)
O2—Mn1—O3ⁱⁱ	178.58 (8)	C9—O5—Mn1ⁱⁱ	135.55 (19)
O3ⁱⁱ—Mn1—O1ⁱ	86.37 (8)	N1—C5—C4	119.9 (3)
O3ⁱⁱ—Mn1—O1	91.92 (8)	N1—C5—H5	120.0
O4—Mn1—O1	91.80 (8)	C4—C5—H5	120.0
O4—Mn1—O1ⁱ	85.20 (8)	C3—C6—H6A	109.5
O4—Mn1—O2	86.30 (9)	C3—C6—H6B	109.5
O4—Mn1—O3ⁱⁱ	93.32 (9)	C3—C6—H6C	109.5
O4—Mn1—O5ⁱ	177.62 (9)	H6A—C6—H6B	109.5
O5ⁱ—Mn1—O1	90.27 (8)	H6A—C6—H6C	109.5
O5ⁱ—Mn1—O1ⁱ	92.69 (8)	H6B—C6—H6C	109.5
O5ⁱ—Mn1—O2	94.99 (9)	O2—C7—C8	117.7 (3)
O5ⁱ—Mn1—O3ⁱⁱ	85.44 (9)	O3—C7—O2	125.5 (3)
Mn1—O1—Mn1ⁱⁱ	112.64 (8)	O3—C7—C8	116.7 (3)
N1—O1—Mn1	123.84 (15)	C7—C8—H8A	109.5
N1—O1—Mn1ⁱⁱ	118.48 (15)	C7—C8—H8B	109.5
N1—C1—H1	120.3	C7—C8—H8C	109.5
N1—C1—C2	119.4 (3)	H8A—C8—H8B	109.5
C2—C1—H1	120.3	H8A—C8—H8C	109.5
C1—N1—O1	118.9 (2)	H8B—C8—H8C	109.5
C1—N1—C5	121.5 (2)	O4—C9—O5	125.3 (3)
C5—N1—O1	119.5 (2)	O4—C9—C10	117.0 (3)
C1—C2—H2	119.3	O5—C9—C10	117.6 (3)
C1—C2—C3	121.5 (3)	C9—C10—H10A	109.5
C3—C2—H2	119.3	C9—C10—H10B	109.5
C7—O2—Mn1	134.09 (19)	C9—C10—H10C	109.5
C7—O3—Mn1ⁱ	138.4 (2)	H10A—C10—H10B	109.5
C2—C3—C4	116.8 (3)	H10A—C10—H10C	109.5
C2—C3—C6	121.5 (3)	H10B—C10—H10C	109.5
C4—C3—C6	121.8 (3)	H6D—O6—H6E	100 (4)
C3—C4—H4	119.5

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6D···O3ⁱⁱⁱ	0.84 (2)	2.23 (2)	3.052 (3)	165 (4)
O6—H6E···O2	0.84 (2)	2.21 (2)	3.035 (3)	170 (4)

Symmetry code: (iii) x, y+1, z.

Funding information

The authors would like to thank Armstrong State University (now Georgia Southern University), Department of Chemistry and Physics for financial support of this work.

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Volume 74| Part 10| October 2018| Pages 1405-1410

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