catena-Poly[[[bis­(μ-4-hydroxy­benzoato)bis­[(4-hydroxy­benzoato)manganese(II)]]-di-μ-4,4′-bipyridine] 4,4′-bipyridine disolvate tetra­hydrate]

Zhao, Q.-H.; Zhao, L.; Wang, K.-M.; Zhou, H.

doi:10.1107/S1600536810007245

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m358

doi:10.1107/S1600536810007245

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catena-Poly[[[bis(μ-4-hydroxybenzoato)bis[(4-hydroxybenzoato)manganese(II)]]-di-μ-4,4′-bipyridine] 4,4′-bipyridine disolvate tetrahydrate]

Qi-Hua Zhao,^a ^* Lei Zhao,^b Kun-Miao Wang ^a and Hong Zhou ^b

^aSchool of Chemical Science and Technology, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 650091, People's Republic of China, and ^bCollege of Basic Science and Information Engineering, Yunnan Agricultural University, Kunming 650201, People's Republic of China
^*Correspondence e-mail: qhzhao@ynu.edu.cn

(Received 12 January 2010; accepted 25 February 2010; online 3 March 2010)

In the polymeric title complex, {[Mn(O₂CC₆H₄-p-OH)₂(C₁₀H₈N₂)]·C₁₀H₈N₂·2H₂O}_n, the Mn^II atom is coordinated in a distorted octahedral geometry defined by four O atoms from three different carboxylate ligands and two trans-N atoms from two 4,4′-bipyridine ligands. In the crystal structure, an extensive range of O—H⋯O and O—H⋯N hydrogen bonds link the complex and all non-coordinated molecules into a three-dimensional network.

Related literature

For background to the use of aromatic carboxylates and 4,4′-bipyridine in the design of supramolecular structures containing metal-organic molecules, see: Leonard et al. (1998 ); Lucia et al. (1997 ); Corey et al. (2001 ).

Experimental

Crystal data

[Mn(C₇H₅O₃)₂(C₁₀H₈N₂)]·C₁₀H₈N₂·2H₂O
M_r = 677.56
Monoclinic, C 2/c
a = 18.1031 (17) Å
b = 11.6448 (11) Å
c = 31.771 (3) Å
β = 104.957 (1)°
V = 6470.6 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 293 K
0.20 × 0.13 × 0.10 mm

Data collection

Bruker APEXII 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.931, T_max = 0.955
20618 measured reflections
7526 independent reflections
4072 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.130
S = 1.01
7526 reflections
428 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2W	0.94	2.00	2.781 (4)	140
O1W—H1WB⋯O2Wⁱ	0.97	2.15	2.992 (4)	145
O2W—H2WB⋯N4	0.89	2.34	2.934 (4)	124
O2W—H2WA⋯O2	0.98	1.82	2.793 (3)	172
O3—H3B⋯N3ⁱⁱ	0.82	1.88	2.694 (4)	169
O6—H6B⋯O1Wⁱⁱⁱ	0.82	1.90	2.701 (4)	167
Symmetry codes: (i) -x, -y, -z+1; (ii) x+1, y, z; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007245/tk2614sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007245/tk2614Isup2.hkl

checkCIF report

Comment top

Much progress has been achieved in the design of supramolecular structures containing metal-organic molecules during recent years. Multifunctional ligands can link metal ions into one-, two- or three-dimensional structures, and in this context, aromatic carboxylates and 4,4'-bipyridine have been used successfully to synthesize such materials (Leonard et al., 1998; Lucia et al., 1997; Corey et al., 2001).

As shown in Fig. 1, the Mn^II coordination environment can be considered as a distorted octahedral geometry, being coordinated by four O atoms in the equatorial plane (O1, O2, O5, O4ⁱⁱ; ii = -x, y, -z+3/2), derived from three different carboxylate groups, and two trans-N atoms (N1, N2ⁱ; i = x, y+1, z). The Mn—O chelating bond distances (2.271 (2) Å and 2.281 (2) Å) are longer than Mn—O bridging bonds (2.087 (2) Å and 2.1102 (19) Å). Pairs of Mn ions are linked via two carboxyl groups to generate an eight-membered Mn₂(COO)₂ ring with a Mn···Mn distance of 4.173 (2) Å. These Mn₂(COO)₂ units are further connected by two 4,4'-bipyridine ligands to form a double-chain structure (Fig. 2) with a Mn—Mn distance 8.355 (4) Å. There are six kinds of H-bonds occurring between the chains, the solvent water and 4,4'-bipyridine molecules, which join the components of the structure into a 3-D network.

Related literature top

For background to the use of aromatic carboxylates and 4,4'-bipyridine in the design of supramolecular structures containing metal-organic molecules, see: Leonard et al. (1998); Lucia et al. (1997); Corey et al. (2001).

Experimental top

Mn(O₂CCH₃)₂ (27.67 mg, 0.1 mmol) was dissolved in H₂O (5 ml), and 4-hydroxybenzoic acid (27.67 mg, 0.2 mmol) was dissolved in methanol (5 ml) at room temperature. The mixture was stirred for 1 h, a methanol solution (5 ml) of 4,4'-bipyridine (31.28 mg, 0.2 mmol) was added, and stirring continued for 30 mins. Yellow single crystals of the title complex were obtained by slow evaporation at room temperature for two weeks.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The immediate environment for the Mn atom in the title complex with the atom-numbering shown for the asymmetric unit. Non-coordinated molecules and hydrogen atoms are omitted for clarity. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. The 1D double chain in the title complex. Non-coordinated molecules and hydrogen atoms are omitted for clarity.

catena-Poly[[[bis(µ-4-hydroxybenzoato)bis[(4- hydroxybenzoato)manganese(II)]]- di-µ-4,4'-bipyridine] 4,4'-bipyridine disolvate tetrahydrate] top

Crystal data top

[Mn(C₇H₅O₃)₂(C₁₀H₈N₂)]·C₁₀H₈N₂·2H₂O	F(000) = 2808
M_r = 677.56	D_x = 1.391 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2470 reflections
a = 18.1031 (17) Å	θ = 2.3–20.7°
b = 11.6448 (11) Å	µ = 0.47 mm⁻¹
c = 31.771 (3) Å	T = 293 K
β = 104.957 (1)°	Irregular, yellow
V = 6470.6 (11) Å³	0.20 × 0.13 × 0.10 mm
Z = 8

Data collection top

Bruker APEXII 1K CCD area-detector diffractometer	7526 independent reflections
Radiation source: fine-focus sealed tube	4072 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ϕ and ω scans	θ_max = 28.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −23→17
T_min = 0.931, T_max = 0.955	k = −15→14
20618 measured reflections	l = −27→41

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0516P)²] where P = (F_o² + 2F_c²)/3
7526 reflections	(Δ/σ)_max = 0.002
428 parameters	Δρ_max = 0.48 e Å⁻³
7 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Mn(C₇H₅O₃)₂(C₁₀H₈N₂)]·C₁₀H₈N₂·2H₂O	V = 6470.6 (11) Å³
M_r = 677.56	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.1031 (17) Å	µ = 0.47 mm⁻¹
b = 11.6448 (11) Å	T = 293 K
c = 31.771 (3) Å	0.20 × 0.13 × 0.10 mm
β = 104.957 (1)°

Data collection top

Bruker APEXII 1K CCD area-detector diffractometer	7526 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4072 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.955	R_int = 0.055
20618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	7 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.01	Δρ_max = 0.48 e Å⁻³
7526 reflections	Δρ_min = −0.34 e Å⁻³
428 parameters

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 > σ(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	0.08008 (2)	0.15824 (3)	0.713098 (13)	0.03256 (13)
O1	0.19470 (11)	0.15352 (16)	0.69639 (6)	0.0465 (5)
O1W	0.06897 (16)	−0.1109 (3)	0.51429 (10)	0.1000 (9)
H1WA	0.0579	−0.0415	0.5263	0.30 (4)*
H1WB	0.0341	−0.1120	0.4856	0.16 (2)*
O2	0.09014 (11)	0.15001 (16)	0.64305 (6)	0.0458 (5)
O2W	0.01136 (14)	0.0156 (3)	0.57296 (8)	0.0980 (10)
H2WB	−0.0031	−0.0486	0.5838	0.23 (4)*
H2WA	0.0431	0.0574	0.5981	0.144 (19)*
O3	0.33963 (13)	0.1358 (2)	0.53460 (7)	0.0775 (8)
H3B	0.3834	0.1140	0.5459	0.116*
O4	0.03921 (11)	0.15809 (17)	0.80555 (7)	0.0573 (6)
O5	0.14062 (11)	0.16769 (16)	0.77935 (6)	0.0483 (5)
O6	0.27872 (16)	0.3557 (2)	0.97038 (8)	0.0966 (9)
H6B	0.3241	0.3623	0.9709	0.145*
N1	0.08390 (12)	−0.03575 (18)	0.71607 (8)	0.0399 (6)
N2	0.08120 (13)	−0.64423 (17)	0.71374 (8)	0.0412 (6)
N3	−0.51598 (16)	0.0563 (3)	0.56051 (11)	0.0741 (9)
N4	−0.12265 (15)	−0.0748 (3)	0.59787 (10)	0.0636 (8)
C1	0.16240 (16)	0.1471 (2)	0.65617 (9)	0.0384 (7)
C2	0.20923 (16)	0.1390 (2)	0.62421 (9)	0.0386 (7)
C3	0.28472 (17)	0.1051 (3)	0.63700 (10)	0.0484 (8)
H3A	0.3061	0.0842	0.6658	0.058*
C4	0.32916 (18)	0.1016 (3)	0.60746 (10)	0.0544 (9)
H4A	0.3797	0.0771	0.6163	0.065*
C5	0.29825 (18)	0.1346 (3)	0.56487 (11)	0.0541 (9)
C6	0.22282 (18)	0.1687 (3)	0.55139 (10)	0.0564 (9)
H6A	0.2020	0.1912	0.5227	0.068*
C7	0.17852 (17)	0.1690 (3)	0.58084 (10)	0.0492 (8)
H7A	0.1273	0.1897	0.5715	0.059*
C8	0.10840 (16)	0.1807 (2)	0.80963 (9)	0.0352 (7)
C9	0.15477 (15)	0.2283 (2)	0.85155 (9)	0.0359 (7)
C10	0.22868 (17)	0.2643 (2)	0.85611 (10)	0.0499 (8)
H10A	0.2502	0.2589	0.8326	0.060*
C11	0.27225 (18)	0.3093 (3)	0.89598 (11)	0.0586 (9)
H11A	0.3220	0.3347	0.8990	0.070*
C12	0.2391 (2)	0.3146 (3)	0.93039 (11)	0.0598 (9)
C13	0.1661 (2)	0.2796 (3)	0.92614 (11)	0.0689 (10)
H13A	0.1446	0.2846	0.9497	0.083*
C14	0.12380 (18)	0.2368 (3)	0.88709 (10)	0.0516 (8)
H14A	0.0737	0.2131	0.8844	0.062*
C15	0.03712 (17)	−0.0965 (2)	0.68436 (10)	0.0548 (9)
H15A	0.0024	−0.0571	0.6624	0.066*
C16	0.03788 (18)	−0.2137 (2)	0.68267 (11)	0.0567 (9)
H16A	0.0044	−0.2518	0.6598	0.068*
C17	0.08816 (15)	−0.2762 (2)	0.71470 (9)	0.0383 (7)
C18	0.13833 (16)	−0.2140 (2)	0.74664 (10)	0.0459 (8)
H18A	0.1746	−0.2514	0.7684	0.055*
C19	0.13412 (16)	−0.0958 (2)	0.74605 (10)	0.0447 (8)
H19A	0.1684	−0.0556	0.7679	0.054*
C20	0.01869 (16)	−0.5805 (2)	0.69826 (10)	0.0468 (8)
H20A	−0.0275	−0.6181	0.6868	0.056*
C21	0.01906 (16)	−0.4630 (2)	0.69834 (10)	0.0470 (8)
H21A	−0.0263	−0.4230	0.6875	0.056*
C22	0.08681 (15)	−0.4033 (2)	0.71451 (9)	0.0379 (7)
C23	0.15139 (16)	−0.4697 (2)	0.73069 (10)	0.0507 (9)
H23A	0.1984	−0.4346	0.7422	0.061*
C24	0.14585 (16)	−0.5868 (2)	0.72969 (11)	0.0514 (9)
H24A	0.1902	−0.6290	0.7409	0.062*
C25	−0.4703 (2)	0.1155 (3)	0.54225 (14)	0.0797 (12)
H25A	−0.4910	0.1766	0.5241	0.096*
C26	−0.3937 (2)	0.0916 (3)	0.54861 (12)	0.0715 (11)
H26A	−0.3643	0.1349	0.5344	0.086*
C27	−0.36040 (18)	0.0029 (3)	0.57622 (10)	0.0514 (8)
C28	−0.40861 (19)	−0.0576 (3)	0.59569 (11)	0.0595 (9)
H28A	−0.3896	−0.1175	0.6148	0.071*
C29	−0.4846 (2)	−0.0285 (3)	0.58664 (12)	0.0719 (11)
H29A	−0.5160	−0.0713	0.5997	0.086*
C30	−0.1652 (2)	−0.0374 (3)	0.56010 (12)	0.0735 (11)
H30A	−0.1418	−0.0279	0.5375	0.088*
C31	−0.24157 (19)	−0.0116 (3)	0.55193 (11)	0.0686 (10)
H31A	−0.2682	0.0145	0.5246	0.082*
C32	−0.27841 (17)	−0.0247 (3)	0.58427 (10)	0.0498 (8)
C33	−0.23480 (19)	−0.0645 (3)	0.62397 (11)	0.0592 (9)
H33A	−0.2567	−0.0756	0.6471	0.071*
C34	−0.1590 (2)	−0.0875 (3)	0.62865 (12)	0.0662 (10)
H34A	−0.1308	−0.1141	0.6556	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0373 (2)	0.0223 (2)	0.0358 (2)	−0.00006 (18)	0.00524 (18)	−0.00108 (19)
O1	0.0462 (12)	0.0540 (12)	0.0382 (12)	−0.0019 (10)	0.0087 (10)	−0.0069 (10)
O1W	0.103 (2)	0.106 (2)	0.084 (2)	0.0188 (18)	0.0113 (19)	0.0147 (18)
O2	0.0410 (12)	0.0535 (13)	0.0409 (12)	0.0010 (10)	0.0071 (9)	−0.0006 (10)
O2W	0.0773 (19)	0.156 (3)	0.0601 (17)	−0.0445 (19)	0.0172 (15)	−0.0286 (19)
O3	0.0578 (15)	0.127 (2)	0.0515 (15)	0.0158 (14)	0.0203 (13)	0.0114 (15)
O4	0.0376 (12)	0.0491 (12)	0.0768 (16)	−0.0018 (10)	−0.0003 (11)	−0.0030 (12)
O5	0.0580 (13)	0.0488 (12)	0.0350 (11)	0.0001 (10)	0.0061 (10)	−0.0049 (10)
O6	0.118 (2)	0.110 (2)	0.0490 (16)	−0.0248 (17)	−0.0017 (15)	−0.0248 (15)
N1	0.0428 (14)	0.0241 (12)	0.0461 (15)	−0.0004 (10)	−0.0005 (11)	0.0037 (11)
N2	0.0447 (14)	0.0238 (12)	0.0501 (15)	0.0004 (11)	0.0035 (12)	−0.0037 (11)
N3	0.0562 (19)	0.092 (3)	0.078 (2)	0.0014 (18)	0.0234 (17)	0.0091 (19)
N4	0.0528 (18)	0.077 (2)	0.059 (2)	−0.0074 (15)	0.0102 (16)	−0.0033 (16)
C1	0.0439 (17)	0.0311 (15)	0.0382 (17)	−0.0037 (13)	0.0070 (14)	−0.0007 (13)
C2	0.0453 (17)	0.0333 (16)	0.0376 (17)	−0.0026 (13)	0.0114 (14)	−0.0021 (13)
C3	0.0444 (19)	0.0562 (19)	0.0400 (18)	0.0027 (15)	0.0026 (15)	−0.0011 (15)
C4	0.0407 (18)	0.079 (2)	0.043 (2)	0.0091 (17)	0.0094 (16)	−0.0028 (18)
C5	0.048 (2)	0.072 (2)	0.044 (2)	0.0008 (17)	0.0159 (17)	−0.0006 (17)
C6	0.056 (2)	0.079 (2)	0.0327 (17)	0.0038 (18)	0.0096 (16)	0.0069 (17)
C7	0.0437 (18)	0.058 (2)	0.0441 (19)	0.0032 (15)	0.0083 (15)	0.0035 (16)
C8	0.0382 (17)	0.0218 (14)	0.0408 (17)	0.0020 (11)	0.0015 (14)	0.0005 (12)
C9	0.0401 (16)	0.0296 (14)	0.0352 (16)	0.0013 (12)	0.0048 (13)	−0.0010 (12)
C10	0.0495 (19)	0.0499 (19)	0.046 (2)	−0.0045 (15)	0.0047 (15)	−0.0024 (15)
C11	0.052 (2)	0.057 (2)	0.059 (2)	−0.0117 (16)	−0.0003 (18)	−0.0025 (18)
C12	0.074 (3)	0.056 (2)	0.042 (2)	−0.0070 (18)	0.0011 (19)	−0.0054 (16)
C13	0.088 (3)	0.071 (3)	0.050 (2)	−0.006 (2)	0.023 (2)	−0.0096 (19)
C14	0.057 (2)	0.051 (2)	0.047 (2)	−0.0006 (16)	0.0128 (17)	−0.0031 (16)
C15	0.060 (2)	0.0326 (17)	0.053 (2)	−0.0013 (15)	−0.0178 (16)	0.0013 (15)
C16	0.069 (2)	0.0290 (16)	0.054 (2)	−0.0061 (15)	−0.0185 (17)	−0.0020 (15)
C17	0.0401 (16)	0.0253 (14)	0.0455 (18)	0.0015 (12)	0.0035 (14)	−0.0010 (13)
C18	0.0521 (18)	0.0268 (15)	0.0468 (19)	0.0032 (13)	−0.0089 (14)	0.0022 (14)
C19	0.0488 (18)	0.0296 (16)	0.0451 (18)	−0.0027 (13)	−0.0074 (14)	−0.0022 (14)
C20	0.0460 (18)	0.0293 (15)	0.057 (2)	−0.0057 (14)	−0.0017 (15)	−0.0003 (14)
C21	0.0410 (17)	0.0270 (15)	0.061 (2)	0.0027 (13)	−0.0077 (15)	0.0016 (14)
C22	0.0450 (17)	0.0209 (14)	0.0428 (17)	0.0008 (12)	0.0022 (14)	0.0000 (13)
C23	0.0393 (17)	0.0292 (15)	0.074 (2)	−0.0012 (13)	−0.0033 (16)	−0.0015 (15)
C24	0.0398 (18)	0.0285 (15)	0.077 (2)	0.0049 (13)	−0.0008 (16)	−0.0007 (16)
C25	0.057 (3)	0.084 (3)	0.092 (3)	0.005 (2)	0.009 (2)	0.024 (2)
C26	0.057 (2)	0.081 (3)	0.074 (3)	−0.012 (2)	0.013 (2)	0.022 (2)
C27	0.055 (2)	0.052 (2)	0.0469 (19)	−0.0095 (16)	0.0112 (16)	0.0000 (16)
C28	0.060 (2)	0.063 (2)	0.062 (2)	0.0013 (18)	0.0262 (19)	0.0100 (18)
C29	0.071 (3)	0.077 (3)	0.077 (3)	−0.004 (2)	0.035 (2)	0.006 (2)
C30	0.053 (2)	0.115 (3)	0.054 (2)	−0.016 (2)	0.0187 (19)	−0.009 (2)
C31	0.048 (2)	0.103 (3)	0.050 (2)	−0.018 (2)	0.0041 (18)	0.006 (2)
C32	0.0447 (19)	0.0517 (19)	0.051 (2)	−0.0126 (15)	0.0084 (17)	−0.0018 (16)
C33	0.062 (2)	0.065 (2)	0.050 (2)	−0.0018 (18)	0.0137 (18)	0.0075 (17)
C34	0.063 (2)	0.077 (3)	0.052 (2)	0.002 (2)	0.0014 (19)	0.0085 (19)

Geometric parameters (Å, º) top

Mn1—O4ⁱ	2.087 (2)	C10—C11	1.409 (4)
Mn1—O5	2.1102 (19)	C10—H10A	0.9300
Mn1—N1	2.261 (2)	C11—C12	1.377 (5)
Mn1—O1	2.271 (2)	C11—H11A	0.9300
Mn1—O2	2.281 (2)	C12—C13	1.357 (4)
Mn1—N2ⁱⁱ	2.300 (2)	C13—C14	1.372 (4)
Mn1—C1	2.627 (3)	C13—H13A	0.9300
O1—C1	1.263 (3)	C14—H14A	0.9300
O1W—H1WA	0.9383	C15—C16	1.366 (4)
O1W—H1WB	0.9656	C15—H15A	0.9300
O2—C1	1.267 (3)	C16—C17	1.384 (4)
O2W—H2WB	0.8897	C16—H16A	0.9300
O2W—H2WA	0.9833	C17—C18	1.380 (4)
O3—C5	1.363 (4)	C17—C22	1.480 (3)
O3—H3B	0.8200	C18—C19	1.378 (4)
O4—C8	1.253 (3)	C18—H18A	0.9300
O4—Mn1ⁱ	2.087 (2)	C19—H19A	0.9300
O5—C8	1.256 (3)	C20—C21	1.368 (4)
O6—C12	1.373 (4)	C20—H20A	0.9300
O6—H6B	0.8200	C21—C22	1.388 (4)
N1—C19	1.333 (3)	C21—H21A	0.9300
N1—C15	1.339 (3)	C22—C23	1.385 (4)
N2—C24	1.330 (3)	C23—C24	1.367 (4)
N2—C20	1.336 (3)	C23—H23A	0.9300
N2—Mn1ⁱⁱⁱ	2.300 (2)	C24—H24A	0.9300
N3—C25	1.320 (4)	C25—C26	1.378 (4)
N3—C29	1.321 (4)	C25—H25A	0.9300
N4—C34	1.320 (4)	C26—C27	1.388 (4)
N4—C30	1.321 (4)	C26—H26A	0.9300
C1—C2	1.484 (4)	C27—C28	1.385 (4)
C2—C3	1.379 (4)	C27—C32	1.475 (4)
C2—C7	1.391 (4)	C28—C29	1.373 (4)
C3—C4	1.385 (4)	C28—H28A	0.9300
C3—H3A	0.9300	C29—H29A	0.9300
C4—C5	1.379 (4)	C30—C31	1.372 (4)
C4—H4A	0.9300	C30—H30A	0.9300
C5—C6	1.380 (4)	C31—C32	1.370 (4)
C6—C7	1.381 (4)	C31—H31A	0.9300
C6—H6A	0.9300	C32—C33	1.384 (4)
C7—H7A	0.9300	C33—C34	1.369 (4)
C8—C9	1.486 (4)	C33—H33A	0.9300
C9—C10	1.374 (4)	C34—H34A	0.9300
C9—C14	1.388 (4)

O4ⁱ—Mn1—O5	121.08 (9)	C12—C11—H11A	120.9
O4ⁱ—Mn1—N1	91.68 (8)	C10—C11—H11A	120.9
O5—Mn1—N1	90.46 (8)	C13—C12—O6	117.3 (3)
O4ⁱ—Mn1—O1	150.99 (8)	C13—C12—C11	121.3 (3)
O5—Mn1—O1	87.92 (8)	O6—C12—C11	121.3 (3)
N1—Mn1—O1	88.03 (8)	C12—C13—C14	120.0 (3)
O4ⁱ—Mn1—O2	93.46 (8)	C12—C13—H13A	120.0
O5—Mn1—O2	145.44 (8)	C14—C13—H13A	120.0
N1—Mn1—O2	89.40 (8)	C13—C14—C9	120.9 (3)
O1—Mn1—O2	57.53 (7)	C13—C14—H14A	119.5
O4ⁱ—Mn1—N2ⁱⁱ	90.54 (8)	C9—C14—H14A	119.5
O5—Mn1—N2ⁱⁱ	86.44 (8)	N1—C15—C16	123.2 (3)
N1—Mn1—N2ⁱⁱ	176.82 (8)	N1—C15—H15A	118.4
O1—Mn1—N2ⁱⁱ	91.13 (8)	C16—C15—H15A	118.4
O2—Mn1—N2ⁱⁱ	92.75 (8)	C15—C16—C17	120.5 (3)
O4ⁱ—Mn1—C1	122.28 (9)	C15—C16—H16A	119.7
O5—Mn1—C1	116.65 (9)	C17—C16—H16A	119.7
N1—Mn1—C1	87.86 (8)	C18—C17—C16	116.6 (2)
O1—Mn1—C1	28.72 (7)	C18—C17—C22	122.4 (2)
O2—Mn1—C1	28.83 (7)	C16—C17—C22	121.1 (2)
N2ⁱⁱ—Mn1—C1	92.88 (8)	C19—C18—C17	119.4 (3)
C1—O1—Mn1	91.46 (17)	C19—C18—H18A	120.3
H1WA—O1W—H1WB	103.8	C17—C18—H18A	120.3
C1—O2—Mn1	90.90 (17)	N1—C19—C18	124.0 (3)
H2WB—O2W—H2WA	105.7	N1—C19—H19A	118.0
C5—O3—H3B	109.5	C18—C19—H19A	118.0
C8—O4—Mn1ⁱ	164.27 (19)	N2—C20—C21	123.4 (3)
C8—O5—Mn1	123.08 (19)	N2—C20—H20A	118.3
C12—O6—H6B	109.5	C21—C20—H20A	118.3
C19—N1—C15	116.3 (2)	C20—C21—C22	120.4 (3)
C19—N1—Mn1	124.21 (18)	C20—C21—H21A	119.8
C15—N1—Mn1	119.35 (18)	C22—C21—H21A	119.8
C24—N2—C20	116.1 (2)	C23—C22—C21	116.0 (2)
C24—N2—Mn1ⁱⁱⁱ	120.75 (18)	C23—C22—C17	123.0 (2)
C20—N2—Mn1ⁱⁱⁱ	123.16 (18)	C21—C22—C17	121.0 (2)
C25—N3—C29	116.8 (3)	C24—C23—C22	119.9 (3)
C34—N4—C30	115.1 (3)	C24—C23—H23A	120.1
O1—C1—O2	120.0 (3)	C22—C23—H23A	120.1
O1—C1—C2	119.9 (3)	N2—C24—C23	124.2 (3)
O2—C1—C2	120.0 (3)	N2—C24—H24A	117.9
O1—C1—Mn1	59.82 (15)	C23—C24—H24A	117.9
O2—C1—Mn1	60.27 (15)	N3—C25—C26	123.4 (4)
C2—C1—Mn1	179.2 (2)	N3—C25—H25A	118.3
C3—C2—C7	118.4 (3)	C26—C25—H25A	118.3
C3—C2—C1	120.9 (3)	C25—C26—C27	120.0 (3)
C7—C2—C1	120.6 (3)	C25—C26—H26A	120.0
C2—C3—C4	120.9 (3)	C27—C26—H26A	120.0
C2—C3—H3A	119.6	C28—C27—C26	116.1 (3)
C4—C3—H3A	119.6	C28—C27—C32	122.3 (3)
C5—C4—C3	119.8 (3)	C26—C27—C32	121.7 (3)
C5—C4—H4A	120.1	C29—C28—C27	119.6 (3)
C3—C4—H4A	120.1	C29—C28—H28A	120.2
O3—C5—C4	122.5 (3)	C27—C28—H28A	120.2
O3—C5—C6	117.3 (3)	N3—C29—C28	124.1 (4)
C4—C5—C6	120.2 (3)	N3—C29—H29A	117.9
C5—C6—C7	119.5 (3)	C28—C29—H29A	117.9
C5—C6—H6A	120.3	N4—C30—C31	124.5 (4)
C7—C6—H6A	120.3	N4—C30—H30A	117.7
C6—C7—C2	121.1 (3)	C31—C30—H30A	117.7
C6—C7—H7A	119.4	C32—C31—C30	119.7 (3)
C2—C7—H7A	119.4	C32—C31—H31A	120.1
O4—C8—O5	123.0 (3)	C30—C31—H31A	120.1
O4—C8—C9	119.3 (3)	C31—C32—C33	116.5 (3)
O5—C8—C9	117.7 (3)	C31—C32—C27	120.6 (3)
C10—C9—C14	118.6 (3)	C33—C32—C27	122.9 (3)
C10—C9—C8	121.2 (3)	C34—C33—C32	119.0 (3)
C14—C9—C8	120.2 (3)	C34—C33—H33A	120.5
C9—C10—C11	120.8 (3)	C32—C33—H33A	120.5
C9—C10—H10A	119.6	N4—C34—C33	125.1 (3)
C11—C10—H10A	119.6	N4—C34—H34A	117.4
C12—C11—C10	118.2 (3)	C33—C34—H34A	117.4

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2W	0.94	2.00	2.781 (4)	140
O1W—H1WB···O2W^iv	0.97	2.15	2.992 (4)	145
O2W—H2WB···N4	0.89	2.34	2.934 (4)	124
O2W—H2WA···O2	0.98	1.82	2.793 (3)	172
O3—H3B···N3^v	0.82	1.88	2.694 (4)	169
O6—H6B···O1W^vi	0.82	1.90	2.701 (4)	167

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

Experimental details

Crystal data
Chemical formula	[Mn(C₇H₅O₃)₂(C₁₀H₈N₂)]·C₁₀H₈N₂·2H₂O
M_r	677.56
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	18.1031 (17), 11.6448 (11), 31.771 (3)
β (°)	104.957 (1)
V (Å³)	6470.6 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.20 × 0.13 × 0.10

Data collection
Diffractometer	Bruker APEXII 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.931, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	20618, 7526, 4072
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.665

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.130, 1.01
No. of reflections	7526
No. of parameters	428
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.34

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2W	0.94	2.00	2.781 (4)	140
O1W—H1WB···O2Wⁱ	0.97	2.15	2.992 (4)	145
O2W—H2WB···N4	0.89	2.34	2.934 (4)	124
O2W—H2WA···O2	0.98	1.82	2.793 (3)	172
O3—H3B···N3ⁱⁱ	0.82	1.88	2.694 (4)	169
O6—H6B···O1Wⁱⁱⁱ	0.82	1.90	2.701 (4)	167

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

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Corey, S., Hu, N.-X. & Wan, S.-N. (2001). J. Chem. Soc. Dalton Trans. pp. 134–137. Google Scholar
Leonard, R., Millivray, R., Groe, M. & Jerry, L. A. (1998). J. Am. Chem. Soc. 212, 2676–2677. Google Scholar
Lucia, C., Gianfranco, C., Davide, M. & Angelo, S. (1997). J. Chem. Soc. Dalton Trans. pp. 1801–1803. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 4| April 2010| Page m358

doi:10.1107/S1600536810007245

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[[[bis­­(μ-4-hy­droxy­benzoato)bis­­[(4-hy­droxy­benzoato)manganese(II)]]-di-μ-4,4′-bi­pyridine] 4,4′-bi­pyridine disolvate tetra­hydrate]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

catena-Poly[[[bis(μ-4-hydroxybenzoato)bis[(4-hydroxybenzoato)manganese(II)]]-di-μ-4,4′-bipyridine] 4,4′-bipyridine disolvate tetrahydrate]