Poly[butane-1,4-di­ammonium [tri-μ-oxalato-dimanganese(II)] hexa­hydrate]

Sadakiyo, M.; Yamada, T.; Kitagawa, H.

doi:10.1107/S2414314616016394

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 11| November 2016| x161639

https://doi.org/10.1107/S2414314616016394

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Poly[butane-1,4-diammonium [tri-μ-oxalato-dimanganese(II)] hexahydrate]

Masaaki Sadakiyo,^a Teppei Yamada ^b and Hiroshi Kitagawa ^b ^*

^aInternational Institute for Carbon-Neutral Energy Research, Kyushu University, Moto-oka 744, Nishi-ku, Fukuoka 819-0395, Japan, and ^bDivision of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa-Oiwakecho, Sakyo-ku, Kyoto 606-8502, Japan
^*Correspondence e-mail: kitagawa@kuchem.kyoto-u.ac.jp

Edited by J. Simpson, University of Otago, New Zealand (Received 10 October 2016; accepted 14 October 2016; online 1 November 2016)

In the title coordination polymer, {(C₄H₁₄N₂)[Mn₂(C₂O₄)₃]·6H₂O}_n, the Mn^II ions are octahedrally coordinated by the oxalate ligands to form a two-dimensional honeycomb-like network. This anionic framework incorporates the centrosymmetric butane-1,4-diammonium ions as counter-cations. The two-dimensional network is slightly distorted as a result of the vertically incorporated cations. Three kinds of water molecules are located in an interlayer space, forming hydrogen bonds with the ammonium cations and the oxalate ligands of the framework.

Keywords: crystal structure; manganese; coordination polymer; oxalate.

CCDC reference: 1509829

Structure description

Oxalate-bridged infinite networks show various functionalities, such as ferromagnetism (Tamaki et al., 1992 ), high proton conduction (Sadakiyo et al., 2009 ) and selective adsorption properties (Sadakiyo et al., 2011 ). In this study, the crystal structure of a new oxalato-bridged manganese(II) two-dimensional network is reported.

There is one crystallographically independent Mn atom in the asymmetric unit and the oxalate ligands form bridges between the Mn^II ions. O atoms of the oxalate ligands coordinate the Mn^II cations in a slightly distorted octahedral geometry, forming a honeycomb-like two-dimensional network of [Mn₂(C₂O₄)₃]²⁻ units which in turn incorporate the butane-1,4-diammonium counter-cations, (Fig. 1). These cations lie on inversion centres located at the midpoint of the C4—C4^iv bond [symmetry code: (iv) −x, −y + 1, −z + 2]. The two-dimensional sheets are stacked to form a layered structure (Fig. 2). In the interlayer space, there are three independent water molecules (O3, O7 and O9) that form hydrogen bonds (Table 1) with both the ammonium substituents of the cation and the O atoms of the oxalate ligands (Fig. 3). The layer structure is distorted to accommodate the presence of the vertically incorporated cations, while other oxalate-bridged two-dimensional coordination polymers generally form a flat layer structure (Clemente-León et al., 1997 ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5	0.81 (2)	2.06 (2)	2.8196 (12)	157.3 (19)
O3—H3A⋯O2ⁱ	0.82 (2)	2.01 (2)	2.8156 (12)	168.8 (19)
O7—H7⋯O4ⁱⁱ	0.85 (2)	2.00 (2)	2.8392 (12)	169.6 (19)
O9—H9⋯O3ⁱⁱⁱ	0.84 (2)	2.02 (2)	2.8565 (15)	173 (2)
O7—H5B⋯O1	0.800 (19)	2.068 (19)	2.8603 (12)	171.1 (18)
O9—H5C⋯O6	0.79 (2)	2.08 (2)	2.8354 (14)	160 (2)
N1—H1⋯O3^iv	0.91	2.05	2.9349 (14)	165
N1—H1A⋯O7ⁱ	0.91	1.99	2.8418 (14)	156
N1—H1B⋯O9ⁱ	0.91	1.92	2.7868 (15)	157
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) x, y, z+1; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The sheet structure of {[Mn₂(C₂O₄)₃]²⁻}_n, incorporating butane-1,4-diammonium cations, with displacement ellipsoids drawn at the 50% probability level.

Figure 2
The layered structure of (C₄N₂H₁₄)[Mn₂(C₂O₄)₃]·6H₂O.

Figure 3
The water molecules included in the interlayer space, with displacement ellipsoids drawn at the 50% probability level.

Synthesis and crystallization

A mixture of manganese (II) acetate tetrahydrate (10 mmol, 2451 mg), oxalic acid dihydrate (20 mmol, 2521 mg), 1,4-diaminobutane (10 mmol, 1.0 ml), and distilled water (550 mmol, 10 ml) was heated in a 50 ml Teflon-lined autoclave. The reaction temperature was controlled using a programmable oven. The mixture was kept at 403 K for 24 h. After that, it was cooled slowly to 298 K over 168 h. Colourless crystals were collected by filtration (several crystals were stored in the mother liquid for structural analysis). After washing the samples with distilled water, the samples were dried under air (yield: 2324 mg, 81%). Elemental analysis calculated for C₁₀H₁₈Mn₂N₂O₁₄ (%): C 24.02, H 3.63, N 5.60; found: C 23.81, H 3.41, N 5.56.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	(C₄H₁₄N₂)[Mn₂(C₂O₄)₃]·6H₂O
M_r	572.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.2623 (8), 16.1821 (15), 9.4702 (9)
β (°)	111.9172 (10)
V (Å³)	1174.66 (19)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.16
Crystal size (mm)	0.15 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )
T_min, T_max	0.846, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	13965, 2975, 2789
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.684

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.056, 1.07
No. of reflections	2975
No. of parameters	170
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.40
Computer programs: APEX2 and SAINT (Bruker, 2007 ), SIR2002 (Burla et al. 2003 ), SHELXL97 (Sheldrick 2008 ), DIAMOND (Brandenburg 1999 ) and Yadokari-XG (Kabuto et al. 2009 ).

Structural data

CCDC reference: 1509829

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314616016394/sj4065sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616016394/sj4065Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR2002 (Burla et al. 2003); program(s) used to refine structure: SHELXL97 (Sheldrick 2008); molecular graphics: DIAMOND (Brandenburg 1999); software used to prepare material for publication: Yadokari-XG (Kabuto et al. 2009).

Poly[butane-1,4-diammonium [tri-µ-oxalato-dimanganese(II)] hexahydrate] top

Crystal data top

(C₄H₁₄N₂)[Mn₂(C₂O₄)₃]·6H₂O	F(000) = 588
M_r = 572.21	D_x = 1.618 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 9419 reflections
a = 8.2623 (8) Å	θ = 2.5–28.9°
b = 16.1821 (15) Å	µ = 1.16 mm⁻¹
c = 9.4702 (9) Å	T = 100 K
β = 111.9172 (10)°	Platelet, colorless
V = 1174.66 (19) Å³	0.15 × 0.15 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEX CCD detector diffractometer	2975 independent reflections
Radiation source: fine-focus sealed tube	2789 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 29.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.846, T_max = 0.944	k = −21→21
13965 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0238P)² + 0.5691P] where P = (F_o² + 2F_c²)/3
2975 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Mn1	0.02869 (2)	0.169789 (10)	0.957930 (18)	0.01373 (6)
O1	−0.25273 (11)	0.17989 (5)	0.83745 (10)	0.01818 (17)
O2	0.04842 (10)	0.26513 (5)	1.12735 (9)	0.01710 (16)
O3	0.24744 (12)	0.17269 (6)	0.66258 (11)	0.02013 (18)
H3	0.197 (3)	0.2048 (13)	0.698 (2)	0.043 (5)*
H3A	0.335 (3)	0.1954 (12)	0.661 (2)	0.037 (5)*
O4	0.30602 (10)	0.19016 (5)	1.06540 (9)	0.01681 (16)
O5	0.00415 (10)	0.24760 (5)	0.76634 (9)	0.01656 (16)
O6	0.00269 (11)	0.08224 (5)	1.12066 (9)	0.01871 (17)
O7	−0.44146 (12)	0.09772 (6)	0.99547 (10)	0.01985 (17)
H7	−0.513 (2)	0.1308 (13)	1.012 (2)	0.041 (5)*
O8	0.04419 (11)	0.05226 (5)	0.85630 (9)	0.01841 (17)
C1	0.35089 (14)	0.23655 (7)	1.17931 (12)	0.0132 (2)
N1	0.19120 (13)	0.49595 (7)	0.76866 (11)	0.0181 (2)
H1	0.2093	0.5515	0.7721	0.027*
H1A	0.1648	0.4776	0.6718	0.027*
H1B	0.2895	0.4702	0.8319	0.027*
C2	−0.29846 (14)	0.22215 (7)	0.71826 (12)	0.0141 (2)
C3	−0.01213 (14)	0.00845 (7)	1.07678 (12)	0.0147 (2)
C4	0.07643 (16)	0.50957 (8)	0.97641 (13)	0.0188 (2)
H4	0.0947	0.5701	0.9786	0.023*
H4A	0.1837	0.4840	1.0498	0.023*
O9	−0.03534 (17)	0.11469 (9)	1.40088 (14)	0.0470 (4)
H9	0.052 (3)	0.1325 (15)	1.473 (2)	0.053 (6)*
C5	0.04384 (16)	0.47715 (8)	0.81809 (13)	0.0203 (2)
H5	0.0265	0.4166	0.8165	0.024*
H5A	−0.0644	0.5022	0.7452	0.024*
H5B	−0.391 (2)	0.1254 (11)	0.955 (2)	0.032 (4)*
H5C	−0.005 (3)	0.1135 (13)	1.331 (3)	0.051 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.01273 (9)	0.01503 (9)	0.01310 (9)	−0.00011 (6)	0.00444 (7)	0.00001 (6)
O1	0.0135 (4)	0.0236 (4)	0.0177 (4)	−0.0004 (3)	0.0062 (3)	0.0064 (3)
O2	0.0117 (4)	0.0197 (4)	0.0190 (4)	0.0013 (3)	0.0047 (3)	−0.0040 (3)
O3	0.0168 (4)	0.0228 (4)	0.0246 (4)	−0.0020 (3)	0.0120 (4)	−0.0020 (3)
O4	0.0128 (4)	0.0211 (4)	0.0165 (4)	0.0007 (3)	0.0055 (3)	−0.0043 (3)
O5	0.0115 (4)	0.0205 (4)	0.0175 (4)	0.0000 (3)	0.0052 (3)	0.0028 (3)
O6	0.0275 (4)	0.0162 (4)	0.0151 (4)	−0.0003 (3)	0.0109 (3)	−0.0009 (3)
O7	0.0204 (4)	0.0204 (4)	0.0237 (4)	0.0017 (3)	0.0139 (4)	0.0027 (3)
O8	0.0248 (4)	0.0172 (4)	0.0171 (4)	−0.0003 (3)	0.0123 (3)	0.0004 (3)
C1	0.0125 (5)	0.0137 (5)	0.0147 (5)	0.0017 (4)	0.0065 (4)	0.0013 (4)
N1	0.0177 (5)	0.0237 (5)	0.0160 (4)	0.0014 (4)	0.0100 (4)	0.0010 (4)
C2	0.0133 (5)	0.0141 (5)	0.0164 (5)	−0.0009 (4)	0.0073 (4)	−0.0005 (4)
C3	0.0132 (5)	0.0185 (5)	0.0129 (5)	0.0008 (4)	0.0054 (4)	−0.0003 (4)
C4	0.0215 (6)	0.0221 (6)	0.0172 (5)	−0.0017 (4)	0.0123 (5)	−0.0007 (4)
O9	0.0439 (7)	0.0779 (9)	0.0282 (6)	−0.0362 (7)	0.0240 (5)	−0.0258 (6)
C5	0.0204 (6)	0.0257 (6)	0.0192 (5)	−0.0053 (5)	0.0122 (5)	−0.0027 (4)

Geometric parameters (Å, º) top

Mn1—O5	2.1549 (8)	C1—C2ⁱ	1.5638 (15)
Mn1—O8	2.1567 (8)	N1—C5	1.4897 (14)
Mn1—O4	2.1573 (8)	N1—H1	0.9100
Mn1—O6	2.1623 (8)	N1—H1A	0.9100
Mn1—O1	2.1805 (9)	N1—H1B	0.9100
Mn1—O2	2.1876 (8)	C2—O2ⁱⁱ	1.2534 (13)
O1—C2	1.2513 (14)	C2—C1ⁱⁱ	1.5638 (15)
O2—C2ⁱ	1.2534 (14)	C3—O8ⁱⁱⁱ	1.2499 (14)
O3—H3	0.81 (2)	C3—C3ⁱⁱⁱ	1.564 (2)
O3—H3A	0.82 (2)	C4—C5	1.5147 (16)
O4—C1	1.2515 (13)	C4—C4^iv	1.520 (2)
O5—C1ⁱⁱ	1.2528 (13)	C4—H4	0.9900
O6—C3	1.2552 (14)	C4—H4A	0.9900
O7—H7	0.85 (2)	O9—H9	0.84 (2)
O7—H5B	0.800 (19)	O9—H5C	0.79 (2)
O8—C3ⁱⁱⁱ	1.2499 (14)	C5—H5	0.9900
C1—O5ⁱ	1.2528 (13)	C5—H5A	0.9900

O5—Mn1—O8	98.17 (3)	C5—N1—H1	109.5
O5—Mn1—O4	93.30 (3)	C5—N1—H1A	109.5
O8—Mn1—O4	96.65 (3)	H1—N1—H1A	109.5
O5—Mn1—O6	168.45 (3)	C5—N1—H1B	109.5
O8—Mn1—O6	77.20 (3)	H1—N1—H1B	109.5
O4—Mn1—O6	97.73 (3)	H1A—N1—H1B	109.5
O5—Mn1—O1	76.63 (3)	O1—C2—O2ⁱⁱ	126.65 (10)
O8—Mn1—O1	93.55 (3)	O1—C2—C1ⁱⁱ	116.56 (9)
O4—Mn1—O1	166.61 (3)	O2ⁱⁱ—C2—C1ⁱⁱ	116.79 (9)
O6—Mn1—O1	92.97 (3)	O8ⁱⁱⁱ—C3—O6	126.36 (10)
O5—Mn1—O2	99.40 (3)	O8ⁱⁱⁱ—C3—C3ⁱⁱⁱ	117.31 (12)
O8—Mn1—O2	161.54 (3)	O6—C3—C3ⁱⁱⁱ	116.33 (12)
O4—Mn1—O2	76.76 (3)	C5—C4—C4^iv	111.11 (13)
O6—Mn1—O2	86.53 (3)	C5—C4—H4	109.4
O1—Mn1—O2	95.96 (3)	C4^iv—C4—H4	109.4
C2—O1—Mn1	114.64 (7)	C5—C4—H4A	109.4
C2ⁱ—O2—Mn1	113.54 (7)	C4^iv—C4—H4A	109.4
H3—O3—H3A	107.9 (19)	H4—C4—H4A	108.0
C1—O4—Mn1	114.78 (7)	H9—O9—H5C	104.1 (19)
C1ⁱⁱ—O5—Mn1	115.33 (7)	N1—C5—C4	112.09 (10)
C3—O6—Mn1	114.25 (7)	N1—C5—H5	109.2
H7—O7—H5B	104.7 (19)	C4—C5—H5	109.2
C3ⁱⁱⁱ—O8—Mn1	114.07 (7)	N1—C5—H5A	109.2
O4—C1—O5ⁱ	126.26 (10)	C4—C5—H5A	109.2
O4—C1—C2ⁱ	116.99 (9)	H5—C5—H5A	107.9
O5ⁱ—C1—C2ⁱ	116.75 (9)

O5—Mn1—O1—C2	1.12 (8)	O2—Mn1—O5—C1ⁱⁱ	−93.12 (8)
O8—Mn1—O1—C2	−96.44 (8)	O5—Mn1—O6—C3	59.66 (19)
O4—Mn1—O1—C2	43.14 (17)	O8—Mn1—O6—C3	−7.78 (8)
O6—Mn1—O1—C2	−173.79 (8)	O4—Mn1—O6—C3	−102.89 (8)
O2—Mn1—O1—C2	99.40 (8)	O1—Mn1—O6—C3	85.19 (8)
O5—Mn1—O2—C2ⁱ	−100.89 (8)	O2—Mn1—O6—C3	−179.01 (8)
O8—Mn1—O2—C2ⁱ	61.08 (14)	O5—Mn1—O8—C3ⁱⁱⁱ	−161.48 (8)
O4—Mn1—O2—C2ⁱ	−9.69 (8)	O4—Mn1—O8—C3ⁱⁱⁱ	104.20 (8)
O6—Mn1—O2—C2ⁱ	89.09 (8)	O6—Mn1—O8—C3ⁱⁱⁱ	7.75 (8)
O1—Mn1—O2—C2ⁱ	−178.27 (8)	O1—Mn1—O8—C3ⁱⁱⁱ	−84.50 (8)
O5—Mn1—O4—C1	106.38 (8)	O2—Mn1—O8—C3ⁱⁱⁱ	36.49 (15)
O8—Mn1—O4—C1	−154.99 (8)	Mn1—O4—C1—O5ⁱ	174.36 (9)
O6—Mn1—O4—C1	−77.06 (8)	Mn1—O4—C1—C2ⁱ	−4.78 (12)
O1—Mn1—O4—C1	65.67 (16)	Mn1—O1—C2—O2ⁱⁱ	177.64 (9)
O2—Mn1—O4—C1	7.50 (8)	Mn1—O1—C2—C1ⁱⁱ	−2.56 (12)
O8—Mn1—O5—C1ⁱⁱ	92.56 (8)	Mn1—O6—C3—O8ⁱⁱⁱ	−173.20 (9)
O4—Mn1—O5—C1ⁱⁱ	−170.24 (8)	Mn1—O6—C3—C3ⁱⁱⁱ	6.79 (15)
O6—Mn1—O5—C1ⁱⁱ	27.1 (2)	C4^iv—C4—C5—N1	179.40 (12)
O1—Mn1—O5—C1ⁱⁱ	0.83 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5	0.81 (2)	2.06 (2)	2.8196 (12)	157.3 (19)
O3—H3A···O2^v	0.82 (2)	2.01 (2)	2.8156 (12)	168.8 (19)
O7—H7···O4^vi	0.85 (2)	2.00 (2)	2.8392 (12)	169.6 (19)
O9—H9···O3^vii	0.84 (2)	2.02 (2)	2.8565 (15)	173 (2)
O7—H5B···O1	0.800 (19)	2.068 (19)	2.8603 (12)	171.1 (18)
O9—H5C···O6	0.79 (2)	2.08 (2)	2.8354 (14)	160 (2)
N1—H1···O3^viii	0.91	2.05	2.9349 (14)	165
N1—H1A···O7^v	0.91	1.99	2.8418 (14)	156
N1—H1B···O9^v	0.91	1.92	2.7868 (15)	157

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

Acknowledgements

The authors gratefully acknowledge financial support from JSPS Research Fellowships for Young Scientists No. 21.4405, Grant-in-Aid for Scientific Research Nos. 20350030 and 22108526.

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