catena-Poly[[[aqua­(2,2′-bipyridine)manganese(II)]-μ-5-methoxy­iso­phthalato-κ3O,O′:O′′] monohydrate]

Shen, S.-M.

doi:10.1107/S1600536809035466

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1173

doi:10.1107/S1600536809035466

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catena-Poly[[[aqua(2,2′-bipyridine)manganese(II)]-μ-5-methoxyisophthalato-κ³O,O′:O′′] monohydrate]

Su-Mei Shen ^a ^*

^aDepartment of Applied Engineering, Zhejiang Economic and Trade Polytechnic, 310018 Hangzhou, People's Republic of China
^*Correspondence e-mail: zjssm01@126.com

(Received 30 August 2009; accepted 2 September 2009; online 5 September 2009)

In the title compound, {[Mn(C₈H₄O₄)(C₁₀H₈N₂)(H₂O)]·H₂O}_n, the Mn^II centre is octahedrally coordinated by three O atoms from two 5-methoxyisophthalate (CH₃O-ip) ligands, a fourth from a coordinated water molecule and two N atoms from one chelating 2,2′-bipyridine (2,2-bipy) ligand. Each pair of adjacent Mn^II atoms is bridged by a CH₃O-ip ligand, forming a helical chain running along a crystallographic 2₁ axis in the c-axis direction. These chains are decorated with 2,2′-bipy ligands on alternating sides. O—H⋯O hydrogen bonding involving the water molecules stabilizes the crystal structure.

Related literature

For related structures, see: Chen & Liu, (2002 ); Liu et al. (2009 ). For the design and controlled synthesis of metal-organic frameworks, see: Kitagawa et al. (2004 ). For the use of 5-methoxyisophthalic acid in synthesis of self-asssembly of porous coordination compounds, see: Ma et al. (2009 ).

Experimental

Crystal data

[Mn(C₈H₄O₄)(C₁₀H₈N₂)(H₂O)]·H₂O
M_r = 441.29
Monoclinic, P 2₁ /c
a = 8.9067 (13) Å
b = 17.367 (3) Å
c = 12.5804 (18) Å
β = 97.176 (2)°
V = 1930.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 298 K
0.19 × 0.14 × 0.09 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.874, T_max = 0.937
11370 measured reflections
3470 independent reflections
2275 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.091
S = 1.02
3470 reflections
275 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H1W⋯O7ⁱ	0.837 (17)	1.832 (18)	2.668 (4)	178 (4)
O6—H2W⋯O3ⁱⁱ	0.846 (17)	1.888 (19)	2.726 (3)	171 (3)
O7—H3W⋯O2ⁱⁱⁱ	0.839 (18)	1.90 (2)	2.724 (3)	169 (4)
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035466/bg2299sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035466/bg2299Isup2.hkl

checkCIF report

Comment top

Much effort has been focused on the design and controlled synthesis of metal-organic frameworks (Kitagawa et al., 2004). Polycarboxylate ligands have received considerable attention, owing to the variety of their coordination modes and structural features. 5-Methoxyisophthalic acid is a potential multi-dentate ligand with a versatile coordination mode, which has been used in self-asssembled porous coordination synthesis (Ma et al., 2009). The title compound, (I), was constructed by two kinds of bridging and chelating ligands under mild condition, CH₃O-ip and 2,2'-bipy which were self-assembled to a one-dimensional neutral metal-organic compound. In this paper, the crystal structure of (I) is presented.

As illustrated in Fig. 1, Mn^II adopts a distorted octahedral geometry, generated by three O atoms from one bidenated-chelating carboxylate and one monodenated carboxylate group from two adjacent CH₃O-ip, a fourth O from a coordinated water molecule, and two N atoms from one chelating 2,2-bipy ligand. The four atoms (O1, O2, O4 and N2) in the equatorial plane around the Mn atom form a highly distorted square-planar arrangement, while the distorted octahedral coordination is completed by the N atom of 2,2-bipy (N1) and the O atom of the water molecule (O6) in the axial positions.

The neighboring Mn atoms are linked by CH₃O-ip ligands forming a one-dimensional helical chain running along a crystallographic 2₁ axis in the c-direction (Fig. 2). These chains are decorated with 2,2'-bipy ligands alternating at both sides, which is similar to some already reported complexes (Chen & Liu, 2002; Liu et al., 2009 ). There are no remarkable π-π interactions between rings of 2,2'-bipy ligands due to its transplacement arrange.

In the crystal structure, strong intermolecular O-H···O hydrogen bonds (Table 2) link the molecules into a 2D network.

Related literature top

For related structures, see: Chen & Liu, (2002); Liu et al. (2009). For the design and controlled synthesis of metal-organic frameworks, see: Kitagawa et al. (2004). For the use of 5-methoxyisophthalic acid in self-asssembled porous coordination synthesis, see: Ma et al. (2009).

Experimental top

The title compound was obtained by direct mixing of equimolar (21mg, 0.1mmol)) Mn(AC)₂ water solution (4mL) and CH₃O-H₂ip (20mg, 0.1mmol), 2,2'-bipy (0.19mg, 0.1mmol) and NaOH (3.8mg, 0.09mmol) 96% methanol solutions (10mL). After a few days, some crystalline material had precipitated, but it was found to be unsuitable for X-ray diffraction. This material was therefore dissolved in water and heated at 398 K for 3 h in a pressurized reactor. Slow evaporation of this solution resulted in the formation of some block crystals of (I), which were suitable for X-ray analysis.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The ORTEP plot of (I), showing the atom-labeling scheme. Ellipsoids are drawn at the the 30% probability level. Symmetry codes: (i) 2-x, y-1/2, 3/2-z; (ii) 2-x, y+1/2, 3/2-z
	Fig. 2. A partial packing virçew of the title compounds, showing the formation of a chain along c axis.

catena-Poly[[[aqua(2,2'-bipyridine)manganese(II)]-µ-5- methoxyisophthalato-κ³O,O':O''] monohydrate] top

Crystal data top

[Mn(C₈H₄O₄)(C₁₀H₈N₂)(H₂O)]·H₂O	F(000) = 908
M_r = 441.29	D_x = 1.518 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3462 reflections
a = 8.9067 (13) Å	θ = 2.6–25.2°
b = 17.367 (3) Å	µ = 0.73 mm⁻¹
c = 12.5804 (18) Å	T = 298 K
β = 97.176 (2)°	Block, yellow
V = 1930.7 (5) Å³	0.19 × 0.14 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3470 independent reflections
Radiation source: fine-focus sealed tube	2275 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.874, T_max = 0.937	k = −20→20
11370 measured reflections	l = −14→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0276P)² + 0.6024P] where P = (F_o² + 2F_c²)/3
3470 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.26 e Å⁻³
6 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Mn(C₈H₄O₄)(C₁₀H₈N₂)(H₂O)]·H₂O	V = 1930.7 (5) Å³
M_r = 441.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9067 (13) Å	µ = 0.73 mm⁻¹
b = 17.367 (3) Å	T = 298 K
c = 12.5804 (18) Å	0.19 × 0.14 × 0.09 mm
β = 97.176 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	3470 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2275 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.937	R_int = 0.061
11370 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	6 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.26 e Å⁻³
3470 reflections	Δρ_min = −0.29 e Å⁻³
275 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 > 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	0.86083 (5)	0.64881 (3)	0.57766 (4)	0.03184 (15)
O1	0.7990 (3)	0.77011 (13)	0.48474 (19)	0.0610 (8)
O2	0.9562 (3)	0.76311 (12)	0.63126 (18)	0.0498 (7)
O3	1.0696 (2)	1.00516 (13)	0.85451 (17)	0.0443 (6)
O4	1.0246 (3)	1.11522 (13)	0.77017 (18)	0.0507 (7)
O5	0.6696 (3)	1.04731 (14)	0.43566 (19)	0.0708 (9)
N1	0.6456 (3)	0.66681 (15)	0.6502 (2)	0.0391 (7)
N2	0.6681 (3)	0.60012 (15)	0.4629 (2)	0.0337 (6)
C1	0.8656 (4)	0.88801 (18)	0.5761 (3)	0.0330 (8)
C2	0.9443 (3)	0.92408 (18)	0.6647 (2)	0.0332 (8)
H2	1.0049	0.8952	0.7155	0.040*
C3	0.9327 (3)	1.00281 (18)	0.6774 (2)	0.0310 (7)
C4	0.8419 (4)	1.04587 (19)	0.6018 (3)	0.0418 (9)
H4	0.8343	1.0989	0.6102	0.050*
C5	0.7631 (4)	1.0102 (2)	0.5143 (3)	0.0453 (9)
C6	0.7755 (4)	0.93092 (18)	0.5017 (3)	0.0417 (9)
H6	0.7225	0.9068	0.4425	0.050*
C7	0.8744 (4)	0.80229 (19)	0.5621 (3)	0.0402 (9)
C8	1.0148 (3)	1.0427 (2)	0.7738 (3)	0.0348 (8)
C9	0.6513 (6)	1.1283 (2)	0.4467 (3)	0.0872 (17)
H9A	0.6116	1.1389	0.5127	0.131*
H9B	0.5824	1.1473	0.3878	0.131*
H9C	0.7475	1.1532	0.4471	0.131*
C10	0.6399 (4)	0.7003 (2)	0.7453 (3)	0.0499 (10)
H10	0.7309	0.7132	0.7860	0.060*
C11	0.5089 (4)	0.7168 (2)	0.7862 (3)	0.0554 (10)
H11	0.5107	0.7407	0.8526	0.067*
C12	0.3748 (4)	0.6973 (2)	0.7273 (3)	0.0607 (11)
H12	0.2835	0.7073	0.7533	0.073*
C13	0.3765 (4)	0.6624 (2)	0.6285 (3)	0.0527 (10)
H13	0.2862	0.6492	0.5872	0.063*
C14	0.5131 (3)	0.64735 (19)	0.5918 (2)	0.0348 (8)
C15	0.5263 (3)	0.60952 (18)	0.4878 (2)	0.0317 (8)
C16	0.4026 (4)	0.5843 (2)	0.4195 (3)	0.0468 (9)
H16	0.3056	0.5903	0.4383	0.056*
C17	0.4231 (4)	0.5504 (2)	0.3238 (3)	0.0532 (10)
H17	0.3403	0.5339	0.2769	0.064*
C18	0.5661 (4)	0.5414 (2)	0.2983 (3)	0.0523 (10)
H18	0.5829	0.5187	0.2338	0.063*
C19	0.6858 (4)	0.5666 (2)	0.3703 (3)	0.0457 (9)
H19	0.7836	0.5598	0.3531	0.055*
O6	1.0261 (3)	0.62274 (13)	0.47247 (18)	0.0421 (6)
H1W	1.037 (4)	0.6603 (12)	0.432 (2)	0.063*
H2W	1.033 (4)	0.5804 (11)	0.440 (2)	0.063*
O7	0.0671 (3)	0.74055 (16)	0.3430 (2)	0.0584 (7)
H3W	0.041 (4)	0.734 (2)	0.2772 (16)	0.088*
H4W	0.016 (4)	0.7774 (18)	0.364 (3)	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0319 (3)	0.0319 (3)	0.0307 (3)	−0.0004 (2)	0.0002 (2)	−0.0032 (2)
O1	0.098 (2)	0.0369 (15)	0.0428 (15)	−0.0028 (14)	−0.0116 (15)	−0.0114 (13)
O2	0.0714 (17)	0.0300 (14)	0.0447 (15)	0.0034 (12)	−0.0057 (13)	0.0006 (12)
O3	0.0495 (15)	0.0450 (15)	0.0357 (14)	−0.0025 (12)	−0.0049 (11)	0.0000 (12)
O4	0.0683 (17)	0.0278 (14)	0.0521 (16)	−0.0073 (12)	−0.0081 (13)	−0.0043 (12)
O5	0.107 (2)	0.0441 (16)	0.0505 (16)	0.0136 (16)	−0.0334 (16)	0.0026 (14)
N1	0.0396 (16)	0.0476 (18)	0.0297 (16)	0.0028 (14)	0.0037 (13)	−0.0038 (14)
N2	0.0332 (15)	0.0381 (17)	0.0299 (15)	−0.0007 (13)	0.0046 (12)	−0.0070 (13)
C1	0.047 (2)	0.0278 (17)	0.0244 (17)	−0.0025 (16)	0.0053 (15)	−0.0002 (15)
C2	0.0362 (19)	0.033 (2)	0.0303 (19)	−0.0003 (15)	0.0046 (15)	0.0053 (15)
C3	0.0375 (18)	0.0296 (19)	0.0264 (18)	−0.0064 (15)	0.0063 (14)	−0.0025 (15)
C4	0.058 (2)	0.0267 (18)	0.039 (2)	0.0013 (17)	−0.0033 (18)	−0.0013 (16)
C5	0.062 (2)	0.039 (2)	0.032 (2)	0.0034 (18)	−0.0067 (18)	0.0023 (17)
C6	0.060 (2)	0.030 (2)	0.032 (2)	−0.0023 (17)	−0.0035 (18)	−0.0043 (16)
C7	0.056 (2)	0.033 (2)	0.033 (2)	−0.0039 (18)	0.0117 (18)	−0.0007 (17)
C8	0.0336 (19)	0.036 (2)	0.036 (2)	−0.0019 (16)	0.0068 (16)	−0.0061 (17)
C9	0.140 (5)	0.044 (3)	0.065 (3)	0.029 (3)	−0.036 (3)	0.000 (2)
C10	0.050 (2)	0.066 (3)	0.034 (2)	−0.001 (2)	0.0065 (18)	−0.0099 (19)
C11	0.065 (3)	0.066 (3)	0.037 (2)	0.013 (2)	0.017 (2)	−0.006 (2)
C12	0.050 (2)	0.079 (3)	0.058 (3)	0.015 (2)	0.024 (2)	0.000 (2)
C13	0.037 (2)	0.071 (3)	0.050 (2)	0.006 (2)	0.0069 (17)	−0.004 (2)
C14	0.0328 (17)	0.0364 (19)	0.0352 (19)	0.0041 (16)	0.0035 (15)	0.0046 (17)
C15	0.0284 (18)	0.0344 (19)	0.0323 (19)	0.0017 (14)	0.0035 (14)	0.0018 (15)
C16	0.0317 (19)	0.067 (3)	0.041 (2)	−0.0044 (18)	0.0006 (16)	−0.007 (2)
C17	0.047 (2)	0.069 (3)	0.041 (2)	−0.015 (2)	−0.0054 (18)	−0.011 (2)
C18	0.050 (2)	0.068 (3)	0.038 (2)	−0.006 (2)	0.0030 (19)	−0.016 (2)
C19	0.038 (2)	0.060 (3)	0.040 (2)	0.0013 (18)	0.0044 (17)	−0.0136 (19)
O6	0.0435 (14)	0.0394 (14)	0.0444 (16)	−0.0025 (13)	0.0090 (12)	−0.0006 (12)
O7	0.0654 (19)	0.0565 (19)	0.0529 (17)	0.0004 (14)	0.0060 (15)	0.0046 (15)

Geometric parameters (Å, º) top

Mn1—O4ⁱ	2.135 (2)	C5—C6	1.392 (4)
Mn1—O6	2.147 (2)	C6—H6	0.9300
Mn1—O2	2.230 (2)	C9—H9A	0.9600
Mn1—N1	2.246 (3)	C9—H9B	0.9600
Mn1—N2	2.264 (2)	C9—H9C	0.9600
Mn1—O1	2.439 (2)	C10—C11	1.364 (5)
O1—C7	1.244 (4)	C10—H10	0.9300
O2—C7	1.261 (4)	C11—C12	1.368 (5)
O3—C8	1.254 (4)	C11—H11	0.9300
O4—C8	1.263 (4)	C12—C13	1.384 (5)
O4—Mn1ⁱⁱ	2.135 (2)	C12—H12	0.9300
O5—C5	1.372 (4)	C13—C14	1.379 (4)
O5—C9	1.424 (4)	C13—H13	0.9300
N1—C10	1.337 (4)	C14—C15	1.482 (4)
N1—C14	1.353 (4)	C15—C16	1.381 (4)
N2—C19	1.330 (4)	C16—C17	1.373 (5)
N2—C15	1.349 (4)	C16—H16	0.9300
C1—C6	1.375 (4)	C17—C18	1.361 (5)
C1—C2	1.389 (4)	C17—H17	0.9300
C1—C7	1.502 (4)	C18—C19	1.381 (4)
C2—C3	1.382 (4)	C18—H18	0.9300
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.388 (4)	O6—H1W	0.837 (17)
C3—C8	1.504 (4)	O6—H2W	0.846 (17)
C4—C5	1.376 (4)	O7—H3W	0.839 (18)
C4—H4	0.9300	O7—H4W	0.847 (18)

O4ⁱ—Mn1—O6	101.98 (9)	O2—C7—C1	119.2 (3)
O4ⁱ—Mn1—O2	81.42 (9)	O3—C8—O4	121.7 (3)
O6—Mn1—O2	96.29 (9)	O3—C8—C3	120.9 (3)
O4ⁱ—Mn1—N1	90.59 (9)	O4—C8—C3	117.4 (3)
O6—Mn1—N1	164.94 (9)	O5—C9—H9A	109.5
O2—Mn1—N1	93.75 (9)	O5—C9—H9B	109.5
O4ⁱ—Mn1—N2	135.16 (10)	H9A—C9—H9B	109.5
O6—Mn1—N2	92.96 (9)	O5—C9—H9C	109.5
O2—Mn1—N2	139.02 (9)	H9A—C9—H9C	109.5
N1—Mn1—N2	72.15 (9)	H9B—C9—H9C	109.5
O4ⁱ—Mn1—O1	136.04 (9)	N1—C10—C11	124.0 (3)
O6—Mn1—O1	91.03 (9)	N1—C10—H10	118.0
O2—Mn1—O1	55.30 (8)	C11—C10—H10	118.0
N1—Mn1—O1	85.48 (9)	C10—C11—C12	118.3 (3)
N2—Mn1—O1	84.78 (9)	C10—C11—H11	120.9
C7—O1—Mn1	86.9 (2)	C12—C11—H11	120.9
C7—O2—Mn1	96.11 (19)	C11—C12—C13	119.2 (4)
C8—O4—Mn1ⁱⁱ	105.5 (2)	C11—C12—H12	120.4
C5—O5—C9	117.4 (3)	C13—C12—H12	120.4
C10—N1—C14	117.8 (3)	C14—C13—C12	119.5 (3)
C10—N1—Mn1	123.6 (2)	C14—C13—H13	120.2
C14—N1—Mn1	118.4 (2)	C12—C13—H13	120.2
C19—N2—C15	118.3 (3)	N1—C14—C13	121.1 (3)
C19—N2—Mn1	124.0 (2)	N1—C14—C15	115.5 (3)
C15—N2—Mn1	117.7 (2)	C13—C14—C15	123.4 (3)
C6—C1—C2	119.7 (3)	N2—C15—C16	121.0 (3)
C6—C1—C7	119.5 (3)	N2—C15—C14	116.0 (3)
C2—C1—C7	120.8 (3)	C16—C15—C14	123.0 (3)
C3—C2—C1	120.1 (3)	C17—C16—C15	119.9 (3)
C3—C2—H2	119.9	C17—C16—H16	120.0
C1—C2—H2	119.9	C15—C16—H16	120.0
C2—C3—C4	119.9 (3)	C18—C17—C16	119.2 (3)
C2—C3—C8	120.9 (3)	C18—C17—H17	120.4
C4—C3—C8	119.1 (3)	C16—C17—H17	120.4
C5—C4—C3	120.1 (3)	C17—C18—C19	118.5 (3)
C5—C4—H4	120.0	C17—C18—H18	120.7
C3—C4—H4	120.0	C19—C18—H18	120.7
O5—C5—C4	124.6 (3)	N2—C19—C18	123.2 (3)
O5—C5—C6	115.6 (3)	N2—C19—H19	118.4
C4—C5—C6	119.8 (3)	C18—C19—H19	118.4
C1—C6—C5	120.4 (3)	Mn1—O6—H1W	110 (2)
C1—C6—H6	119.8	Mn1—O6—H2W	125 (2)
C5—C6—H6	119.8	H1W—O6—H2W	112 (3)
O1—C7—O2	120.4 (3)	H3W—O7—H4W	108 (3)
O1—C7—C1	120.4 (3)

O4ⁱ—Mn1—O1—C7	5.0 (3)	O5—C5—C6—C1	−179.7 (3)
O6—Mn1—O1—C7	−103.5 (2)	C4—C5—C6—C1	0.2 (5)
O2—Mn1—O1—C7	−6.56 (19)	Mn1—O1—C7—O2	11.1 (3)
N1—Mn1—O1—C7	91.2 (2)	Mn1—O1—C7—C1	−167.1 (3)
N2—Mn1—O1—C7	163.6 (2)	Mn1—O2—C7—O1	−12.2 (4)
O4ⁱ—Mn1—O2—C7	−165.4 (2)	Mn1—O2—C7—C1	166.0 (3)
O6—Mn1—O2—C7	93.4 (2)	C6—C1—C7—O1	−1.1 (5)
N1—Mn1—O2—C7	−75.4 (2)	C2—C1—C7—O1	177.2 (3)
N2—Mn1—O2—C7	−8.5 (3)	C6—C1—C7—O2	−179.3 (3)
O1—Mn1—O2—C7	6.50 (19)	C2—C1—C7—O2	−1.0 (5)
O4ⁱ—Mn1—N1—C10	41.7 (3)	Mn1ⁱⁱ—O4—C8—O3	−1.6 (4)
O6—Mn1—N1—C10	−171.5 (3)	Mn1ⁱⁱ—O4—C8—C3	177.8 (2)
O2—Mn1—N1—C10	−39.8 (3)	C2—C3—C8—O3	−14.7 (5)
N2—Mn1—N1—C10	179.6 (3)	C4—C3—C8—O3	164.0 (3)
O1—Mn1—N1—C10	−94.5 (3)	C2—C3—C8—O4	166.0 (3)
O4ⁱ—Mn1—N1—C14	−142.8 (2)	C4—C3—C8—O4	−15.4 (4)
O6—Mn1—N1—C14	4.0 (5)	C14—N1—C10—C11	−0.8 (5)
O2—Mn1—N1—C14	135.8 (2)	Mn1—N1—C10—C11	174.8 (3)
N2—Mn1—N1—C14	−4.9 (2)	N1—C10—C11—C12	0.7 (6)
O1—Mn1—N1—C14	81.0 (2)	C10—C11—C12—C13	−0.6 (6)
O4ⁱ—Mn1—N2—C19	−107.3 (3)	C11—C12—C13—C14	0.6 (6)
O6—Mn1—N2—C19	3.0 (3)	C10—N1—C14—C13	0.8 (5)
O2—Mn1—N2—C19	106.1 (3)	Mn1—N1—C14—C13	−175.0 (3)
N1—Mn1—N2—C19	−179.3 (3)	C10—N1—C14—C15	−179.2 (3)
O1—Mn1—N2—C19	93.7 (3)	Mn1—N1—C14—C15	5.0 (4)
O4ⁱ—Mn1—N2—C15	76.3 (3)	C12—C13—C14—N1	−0.7 (5)
O6—Mn1—N2—C15	−173.4 (2)	C12—C13—C14—C15	179.3 (3)
O2—Mn1—N2—C15	−70.3 (3)	C19—N2—C15—C16	0.6 (5)
N1—Mn1—N2—C15	4.3 (2)	Mn1—N2—C15—C16	177.2 (2)
O1—Mn1—N2—C15	−82.6 (2)	C19—N2—C15—C14	−179.9 (3)
C6—C1—C2—C3	−0.4 (5)	Mn1—N2—C15—C14	−3.3 (4)
C7—C1—C2—C3	−178.7 (3)	N1—C14—C15—N2	−1.0 (4)
C1—C2—C3—C4	0.2 (5)	C13—C14—C15—N2	178.9 (3)
C1—C2—C3—C8	178.9 (3)	N1—C14—C15—C16	178.4 (3)
C2—C3—C4—C5	0.2 (5)	C13—C14—C15—C16	−1.6 (5)
C8—C3—C4—C5	−178.5 (3)	N2—C15—C16—C17	−1.2 (5)
C9—O5—C5—C4	−1.1 (6)	C14—C15—C16—C17	179.3 (3)
C9—O5—C5—C6	178.7 (4)	C15—C16—C17—C18	0.8 (6)
C3—C4—C5—O5	179.5 (3)	C16—C17—C18—C19	0.1 (6)
C3—C4—C5—C6	−0.4 (5)	C15—N2—C19—C18	0.4 (5)
C2—C1—C6—C5	0.2 (5)	Mn1—N2—C19—C18	−176.0 (3)
C7—C1—C6—C5	178.6 (3)	C17—C18—C19—N2	−0.8 (6)

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+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—H1W···O7ⁱⁱⁱ	0.84 (2)	1.83 (2)	2.668 (4)	178 (4)
O6—H2W···O3^iv	0.85 (2)	1.89 (2)	2.726 (3)	171 (3)
O7—H3W···O2^v	0.84 (2)	1.90 (2)	2.724 (3)	169 (4)

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

Experimental details

Crystal data
Chemical formula	[Mn(C₈H₄O₄)(C₁₀H₈N₂)(H₂O)]·H₂O
M_r	441.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.9067 (13), 17.367 (3), 12.5804 (18)
β (°)	97.176 (2)
V (Å³)	1930.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.19 × 0.14 × 0.09

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.874, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	11370, 3470, 2275
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.091, 1.02
No. of reflections	3470
No. of parameters	275
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.29

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H1W···O7ⁱ	0.837 (17)	1.832 (18)	2.668 (4)	178 (4)
O6—H2W···O3ⁱⁱ	0.846 (17)	1.888 (19)	2.726 (3)	171 (3)
O7—H3W···O2ⁱⁱⁱ	0.839 (18)	1.90 (2)	2.724 (3)	169 (4)

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

Acknowledgements

The authors are grateful to the Zhejiang Economic and Trade Polytechnic for financial support. Professor Jean-Claude Daran is thanked for his great help with the refinement.

References

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