catena-Poly[[[diaqua­(1,3-benzimidazole-κN3)manganese(II)]-μ-benzene-1,3-di­carboxyl­ato-κ3O1,O1′:O3] dihydrate]

Wang, X.-H.

doi:10.1107/S1600536811008555

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m423-m424

doi:10.1107/S1600536811008555

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catena-Poly[[[diaqua(1,3-benzimidazole-κN³)manganese(II)]-μ-benzene-1,3-dicarboxylato-κ³O¹,O^1′:O³] dihydrate]

Xiao-Hui Wang ^a ^*

^aZhejiang College of Construction, Hangzhou 311231, People's Republic of China
^*Correspondence e-mail: hzwxh2000@yahoo.com.cn

(Received 28 February 2011; accepted 6 March 2011; online 12 March 2011)

In the polymeric title complex, {[Mn(C₈H₄O₄)(C₇H₆N₂)(H₂O)₂]·2H₂O}_n, the Mn^II cation is coordinated by two benzenedicarboxylate anions, one benzimidazole ligand and two water molecules in a distorted MnNO₅ octahedral geometry. In the crystal, each benzenedicarboxylate anion bridges adjacent Mn^II cations through the terminal carboxylate groups, forming a polymeric complex chain along the a axis. One Mn—O_carboxylate bond is much longer than the others. In the crystal, π–π stacking is observed between nearly parallel [dihedral angle = 4.32 (6)°] benzimidazole aromatic ring systems of adjacent molecules, the centroid–centroid distance between the imidazole and benzene rings being 3.5421 (11) Å. Extensive intermolecular O—H⋯O and N—H⋯O hydrogen bonding is present in the crystal structure. The two lattice water molecules are located on twofold rotation axes.

Related literature

For background to π–π stacking, see: Deisenhofer & Michel (1989 ). For a related structure, see: Hu et al. (2006 ). For a longer Mn—O bond length in complex with a seven-coordinate Mn^II atom, see: Liu et al. (2005 ).

Experimental

Crystal data

[Mn(C₈H₄O₄)(C₇H₆N₂)(H₂O)₂]·2H₂O
M_r = 409.25
Orthorhombic, P b c n
a = 18.9148 (12) Å
b = 23.7112 (16) Å
c = 7.8701 (4) Å
V = 3529.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 292 K
0.24 × 0.20 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.786, T_max = 0.880
20574 measured reflections
4043 independent reflections
3261 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.091
S = 1.04
4043 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn—N3	2.1657 (15)
Mn—O2ⁱ	2.0995 (13)
Mn—O3	2.1832 (13)
Mn—O4	2.6075 (16)
Mn—O5	2.1642 (14)
Mn—O6	2.1674 (14)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O9ⁱⁱ	0.86	1.94	2.795 (2)	171
O5—H5A⋯O4ⁱⁱⁱ	0.89	1.89	2.7605 (18)	168
O5—H5B⋯O1^iv	0.88	1.96	2.8120 (18)	164
O6—H6A⋯O4^v	0.85	1.95	2.7553 (18)	159
O6—H6B⋯O1^vi	0.86	1.88	2.7379 (18)	176
O7—H7A⋯O1	0.95	1.99	2.8844 (18)	155
O8—H8A⋯O3	0.94	1.79	2.7303 (18)	176
O9—H9A⋯O7	0.94	1.92	2.846 (2)	167
O9—H9B⋯O8	0.91	1.92	2.799 (2)	162
Symmetry codes: (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (v) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vi) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008555/xu5169sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008555/xu5169Isup2.hkl

checkCIF report

Comment top

π-π Stacking between aromatic rings plays an important role in the electron transfer process in some biological system (Deisenhofer & Michel, 1989). Many structures of metal complexes incorporating aromatic ring ligands have been reported (Hu & Lai, 2006). The title Mn^II complex includes both of benzimidazole (bzim) and benzendicarboxylate (bdc) aromatic ring ligands, its crystal structure is presented here.

A fragment of the title polymeric Mn^II complex, together with lattice water molecules, is shown in Fig. 1. The Mn^II ion is surrounded by two bdc anions, one bzim and two coordination water molecules in a distorted octahedral geometry. Each bdc anion bridges two Mn^II ions to form the one dimensional polymeric chain running along the a axis. The Mn—O4 distance of 2.6075 (16) Å is much longer than the Mn—O3 bond distance (Table 1) but is comparable to 2.5356 (16) Å found in a seven-coordination Mn^II complex (Liu et al. 2005).

In the crystal structure, the partially overlapped arrangement is observed between nearly parallel bzim ring systems [dihedral angle 4.32 (6)°] (Fig. 2); the centroid-to-centroid separation between the N3-imidazole and C9ⁱ-benzene rings is 3.5421 (11) Å (symmetry code: (ii) (x, 1 - y, -1/2 + z), indicating the existence of π-π stacking between bzim ring systems of the adjacent molecules.

In the asymmetric unit two lattice water molecules locate on twofold rotation axes and are hydrogen bonded to the carboxyl groups of the complex, while the other lattice water molecule locates on a general position and links with bzim ligand of the complex via N—H···O hydrogen bonding (Table 2). Lattice water molecules are linked together via O—H···O hydrogen bonding and filled in the cavity formed by the polymeric complex chains (Fig. 3).

Related literature top

For background to π–π stacking, see: Deisenhofer & Michel (1989). For a related structure, see: Hu & Lai (2006). For a longer Mn—O bond length in complex with a seven-coordinate Mn^II atom, see: Liu et al. (2005).

Experimental top

An ethanol solution (5 ml) of benzimidazole (0.236 g, 2 mmol) was mixed with an aqueous solution (5 ml) of manganese(II) acetate tetrahydrate (0.490 g, 2 mmol) at room temperature. The solution was refluxed for 30 min. Then an aqueous solution (8 ml) containing 1,3-benzenedicarboxylic acid (0.332 g, 2 mmol) and NaOH (0.160 g, 4 mmol) was added dropwise into the above solution. The mixture was refluxed for a further 2 h. After cooling to room temperature the solution was filtered. Single crystals of the title compound were obtained from the filtrate after 2 week.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A fragment of the polymeric structure of (I) with 40% probability displacement ellipsoids (arbitrary spheres for H atoms) [symmetry code: (i) 1/2 + x,3/2 - y,1 - z].
	Fig. 2. A diagram showing the partially overlapped arrangement between aromatic rings [symmetry code: (ii) x,1 - y,-1/2 + z].

catena-Poly[[[diaqua(1,3-benzimidazole-κN³)manganese(II)]- µ-benzene-1,3-dicarboxylato-κ³O¹,O^1':O³] dihydrate] top

Crystal data top

[Mn(C₈H₄O₄)(C₇H₆N₂)(H₂O)₂]·2H₂O	F(000) = 1688
M_r = 409.25	D_x = 1.540 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 8868 reflections
a = 18.9148 (12) Å	θ = 3.0–25.0°
b = 23.7112 (16) Å	µ = 0.79 mm⁻¹
c = 7.8701 (4) Å	T = 292 K
V = 3529.7 (4) Å³	Prism, yellow
Z = 8	0.24 × 0.20 × 0.18 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4043 independent reflections
Radiation source: fine-focus sealed tube	3261 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 27.5°, θ_min = 2.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −24→20
T_min = 0.786, T_max = 0.880	k = −30→30
20574 measured reflections	l = −10→7

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0428P)² + 2.5725P] where P = (F_o² + 2F_c²)/3
4043 reflections	(Δ/σ)_max = 0.002
236 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Mn(C₈H₄O₄)(C₇H₆N₂)(H₂O)₂]·2H₂O	V = 3529.7 (4) Å³
M_r = 409.25	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 18.9148 (12) Å	µ = 0.79 mm⁻¹
b = 23.7112 (16) Å	T = 292 K
c = 7.8701 (4) Å	0.24 × 0.20 × 0.18 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4043 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3261 reflections with I > 2σ(I)
T_min = 0.786, T_max = 0.880	R_int = 0.029
20574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
4043 reflections	Δρ_min = −0.26 e Å⁻³
236 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Mn	0.714708 (13)	0.679735 (11)	0.66543 (3)	0.01758 (9)
N1	0.63968 (9)	0.50825 (7)	0.6050 (2)	0.0300 (4)
H1	0.6084	0.4848	0.5691	0.036*
N3	0.69188 (8)	0.59024 (6)	0.66113 (19)	0.0227 (3)
O1	0.37986 (7)	0.73206 (5)	0.33053 (17)	0.0255 (3)
O2	0.32557 (7)	0.81586 (6)	0.33551 (17)	0.0278 (3)
O3	0.60704 (7)	0.71200 (6)	0.64217 (17)	0.0283 (3)
O4	0.67794 (7)	0.78568 (7)	0.65720 (16)	0.0305 (3)
O5	0.71498 (6)	0.68148 (5)	0.94037 (17)	0.0232 (3)
H5A	0.7534	0.6897	1.0001	0.035*
H5B	0.6793	0.6937	1.0010	0.035*
O6	0.71830 (6)	0.69029 (5)	0.39202 (17)	0.0234 (3)
H6A	0.7572	0.6963	0.3418	0.035*
H6B	0.6861	0.7025	0.3247	0.035*
O7	0.5000	0.66207 (9)	0.2500	0.0384 (5)
H7A	0.4605	0.6869	0.2419	0.058*
O8	0.5000	0.64354 (8)	0.7500	0.0321 (4)
H8A	0.5364	0.6685	0.7171	0.048*
O9	0.45942 (9)	0.57472 (7)	0.4780 (2)	0.0496 (4)
H9A	0.4713	0.5996	0.3886	0.074*
H9B	0.4773	0.5905	0.5737	0.074*
C2	0.63681 (10)	0.56472 (8)	0.5930 (2)	0.0277 (4)
H2	0.5996	0.5839	0.5417	0.033*
C4	0.79996 (10)	0.54864 (8)	0.8052 (2)	0.0270 (4)
H4	0.8220	0.5827	0.8297	0.032*
C5	0.83029 (11)	0.49747 (9)	0.8501 (3)	0.0333 (5)
H5	0.8739	0.4972	0.9049	0.040*
C6	0.79648 (12)	0.44598 (9)	0.8146 (3)	0.0357 (5)
H6	0.8180	0.4125	0.8482	0.043*
C7	0.73256 (12)	0.44362 (8)	0.7318 (3)	0.0340 (5)
H7	0.7106	0.4094	0.7077	0.041*
C8	0.70224 (11)	0.49489 (8)	0.6857 (2)	0.0264 (4)
C9	0.73497 (10)	0.54671 (7)	0.7219 (2)	0.0229 (4)
C10	0.37791 (9)	0.78435 (8)	0.3620 (2)	0.0215 (4)
C11	0.44298 (9)	0.81128 (7)	0.4375 (2)	0.0202 (3)
C12	0.49726 (9)	0.77770 (7)	0.5012 (2)	0.0203 (3)
H12	0.4924	0.7387	0.5003	0.024*
C13	0.55886 (9)	0.80183 (8)	0.5661 (2)	0.0217 (4)
C14	0.56567 (10)	0.86047 (8)	0.5684 (2)	0.0275 (4)
H14	0.6069	0.8770	0.6095	0.033*
C15	0.51092 (11)	0.89410 (8)	0.5092 (3)	0.0315 (4)
H15	0.5152	0.9331	0.5134	0.038*
C16	0.44988 (10)	0.86999 (8)	0.4437 (2)	0.0255 (4)
H16	0.4135	0.8929	0.4038	0.031*
C17	0.61786 (9)	0.76481 (8)	0.6275 (2)	0.0242 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn	0.01342 (14)	0.02063 (14)	0.01869 (15)	0.00030 (9)	0.00052 (9)	0.00094 (10)
N1	0.0311 (9)	0.0279 (8)	0.0310 (9)	−0.0081 (7)	0.0018 (7)	−0.0039 (7)
N3	0.0232 (7)	0.0235 (8)	0.0215 (8)	0.0005 (6)	0.0010 (6)	−0.0007 (6)
O1	0.0192 (6)	0.0291 (7)	0.0282 (7)	−0.0034 (5)	−0.0031 (5)	−0.0002 (5)
O2	0.0157 (6)	0.0364 (7)	0.0313 (8)	0.0021 (5)	−0.0017 (5)	0.0056 (6)
O3	0.0188 (6)	0.0350 (7)	0.0310 (7)	0.0057 (5)	0.0008 (5)	0.0066 (6)
O4	0.0143 (6)	0.0546 (9)	0.0226 (7)	−0.0021 (6)	−0.0021 (5)	0.0012 (6)
O5	0.0179 (6)	0.0317 (7)	0.0201 (6)	−0.0003 (5)	0.0006 (5)	−0.0032 (5)
O6	0.0184 (6)	0.0324 (7)	0.0195 (6)	0.0012 (5)	0.0016 (5)	0.0048 (5)
O7	0.0381 (12)	0.0359 (11)	0.0413 (13)	0.000	0.0073 (10)	0.000
O8	0.0264 (10)	0.0320 (10)	0.0379 (12)	0.000	0.0047 (9)	0.000
O9	0.0577 (11)	0.0495 (10)	0.0417 (10)	−0.0234 (8)	−0.0079 (8)	0.0003 (8)
C2	0.0271 (10)	0.0297 (10)	0.0264 (10)	−0.0010 (8)	0.0011 (8)	−0.0030 (8)
C4	0.0273 (10)	0.0285 (9)	0.0253 (10)	−0.0021 (7)	0.0028 (7)	0.0022 (7)
C5	0.0318 (11)	0.0394 (11)	0.0288 (11)	0.0076 (9)	0.0014 (8)	0.0056 (8)
C6	0.0468 (13)	0.0282 (10)	0.0321 (11)	0.0115 (9)	0.0113 (9)	0.0069 (8)
C7	0.0491 (13)	0.0219 (9)	0.0310 (11)	−0.0005 (8)	0.0116 (9)	0.0003 (8)
C8	0.0317 (10)	0.0250 (9)	0.0224 (9)	−0.0036 (7)	0.0070 (8)	−0.0010 (7)
C9	0.0271 (9)	0.0219 (8)	0.0195 (9)	0.0004 (7)	0.0056 (7)	0.0010 (7)
C10	0.0156 (8)	0.0308 (9)	0.0179 (8)	−0.0014 (6)	0.0015 (6)	0.0033 (7)
C11	0.0149 (8)	0.0288 (9)	0.0170 (8)	0.0004 (6)	0.0012 (6)	0.0001 (7)
C12	0.0172 (8)	0.0259 (8)	0.0178 (8)	0.0003 (6)	0.0022 (6)	−0.0008 (7)
C13	0.0171 (8)	0.0309 (9)	0.0171 (8)	0.0006 (7)	0.0009 (7)	−0.0002 (7)
C14	0.0213 (9)	0.0345 (10)	0.0267 (10)	−0.0058 (7)	−0.0030 (7)	−0.0035 (8)
C15	0.0311 (11)	0.0261 (9)	0.0373 (12)	−0.0019 (8)	−0.0034 (9)	−0.0019 (8)
C16	0.0214 (9)	0.0287 (9)	0.0265 (9)	0.0047 (7)	−0.0011 (7)	0.0008 (7)
C17	0.0164 (8)	0.0396 (11)	0.0165 (8)	0.0035 (7)	0.0023 (6)	0.0003 (7)

Geometric parameters (Å, º) top

Mn—N3	2.1657 (15)	C2—H2	0.9300
Mn—O2ⁱ	2.0995 (13)	C4—C5	1.388 (3)
Mn—O3	2.1832 (13)	C4—C9	1.394 (3)
Mn—O4	2.6075 (16)	C4—H4	0.9300
Mn—O5	2.1642 (14)	C5—C6	1.406 (3)
Mn—O6	2.1674 (14)	C5—H5	0.9300
N1—C2	1.343 (2)	C6—C7	1.375 (3)
N1—C8	1.380 (3)	C6—H6	0.9300
N1—H1	0.8600	C7—C8	1.392 (3)
N3—C2	1.319 (2)	C7—H7	0.9300
N3—C9	1.400 (2)	C8—C9	1.405 (3)
O1—C10	1.265 (2)	C10—C11	1.509 (2)
O2—C10	1.258 (2)	C11—C12	1.393 (2)
O3—C17	1.274 (2)	C11—C16	1.399 (3)
O4—C17	1.261 (2)	C12—C13	1.395 (2)
O5—H5A	0.8866	C12—H12	0.9300
O5—H5B	0.8758	C13—C14	1.396 (3)
O6—H6A	0.8469	C13—C17	1.500 (2)
O6—H6B	0.8576	C14—C15	1.388 (3)
O7—H7A	0.9532	C14—H14	0.9300
O8—H8A	0.9437	C15—C16	1.388 (3)
O9—H9A	0.9455	C15—H15	0.9300
O9—H9B	0.9065	C16—H16	0.9300

O2ⁱ—Mn—O5	90.01 (5)	C7—C6—H6	119.0
O2ⁱ—Mn—N3	104.35 (6)	C5—C6—H6	119.0
O5—Mn—N3	92.00 (5)	C6—C7—C8	116.76 (19)
O2ⁱ—Mn—O6	87.68 (5)	C6—C7—H7	121.6
O5—Mn—O6	172.03 (5)	C8—C7—H7	121.6
N3—Mn—O6	95.96 (5)	N1—C8—C7	132.35 (19)
O2ⁱ—Mn—O3	156.06 (5)	N1—C8—C9	105.70 (16)
O5—Mn—O3	94.55 (5)	C7—C8—C9	121.95 (19)
N3—Mn—O3	98.98 (6)	C4—C9—N3	130.56 (17)
O6—Mn—O3	84.58 (5)	C4—C9—C8	120.85 (17)
C2—N1—C8	107.21 (16)	N3—C9—C8	108.60 (16)
C2—N1—H1	126.4	O2—C10—O1	124.95 (16)
C8—N1—H1	126.4	O2—C10—C11	117.13 (16)
C2—N3—C9	105.11 (15)	O1—C10—C11	117.92 (15)
C2—N3—Mn	127.84 (13)	C12—C11—C16	119.20 (16)
C9—N3—Mn	126.95 (12)	C12—C11—C10	120.08 (15)
C10—O2—Mnⁱⁱ	144.73 (12)	C16—C11—C10	120.72 (16)
C17—O3—Mn	101.66 (11)	C11—C12—C13	120.86 (16)
Mn—O5—H5A	122.4	C11—C12—H12	119.6
Mn—O5—H5B	123.3	C13—C12—H12	119.6
H5A—O5—H5B	105.7	C12—C13—C14	119.34 (16)
Mn—O6—H6A	120.7	C12—C13—C17	119.96 (16)
Mn—O6—H6B	129.0	C14—C13—C17	120.67 (16)
H6A—O6—H6B	105.8	C15—C14—C13	119.94 (17)
H9A—O9—H9B	105.8	C15—C14—H14	120.0
N3—C2—N1	113.38 (18)	C13—C14—H14	120.0
N3—C2—H2	123.3	C14—C15—C16	120.60 (18)
N1—C2—H2	123.3	C14—C15—H15	119.7
C5—C4—C9	117.11 (18)	C16—C15—H15	119.7
C5—C4—H4	121.4	C15—C16—C11	120.02 (17)
C9—C4—H4	121.4	C15—C16—H16	120.0
C4—C5—C6	121.4 (2)	C11—C16—H16	120.0
C4—C5—H5	119.3	O4—C17—O3	120.89 (17)
C6—C5—H5	119.3	O4—C17—C13	120.04 (17)
C7—C6—C5	121.98 (19)	O3—C17—C13	119.01 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O9ⁱⁱⁱ	0.86	1.94	2.795 (2)	171
O5—H5A···O4^iv	0.89	1.89	2.7605 (18)	168
O5—H5B···O1^v	0.88	1.96	2.8120 (18)	164
O6—H6A···O4^vi	0.85	1.95	2.7553 (18)	159
O6—H6B···O1^vii	0.86	1.88	2.7379 (18)	176
O7—H7A···O1	0.95	1.99	2.8844 (18)	155
O8—H8A···O3	0.94	1.79	2.7303 (18)	176
O9—H9A···O7	0.94	1.92	2.846 (2)	167
O9—H9B···O8	0.91	1.92	2.799 (2)	162

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

Experimental details

Crystal data
Chemical formula	[Mn(C₈H₄O₄)(C₇H₆N₂)(H₂O)₂]·2H₂O
M_r	409.25
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	292
a, b, c (Å)	18.9148 (12), 23.7112 (16), 7.8701 (4)
V (Å³)	3529.7 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.786, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections	20574, 4043, 3261
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.091, 1.04
No. of reflections	4043
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.26

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Mn—N3	2.1657 (15)	Mn—O4	2.6075 (16)
Mn—O2ⁱ	2.0995 (13)	Mn—O5	2.1642 (14)
Mn—O3	2.1832 (13)	Mn—O6	2.1674 (14)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O9ⁱⁱ	0.86	1.94	2.795 (2)	171
O5—H5A···O4ⁱⁱⁱ	0.89	1.89	2.7605 (18)	168
O5—H5B···O1^iv	0.88	1.96	2.8120 (18)	164
O6—H6A···O4^v	0.85	1.95	2.7553 (18)	159
O6—H6B···O1^vi	0.86	1.88	2.7379 (18)	176
O7—H7A···O1	0.95	1.99	2.8844 (18)	155
O8—H8A···O3	0.94	1.79	2.7303 (18)	176
O9—H9A···O7	0.94	1.92	2.846 (2)	167
O9—H9B···O8	0.91	1.92	2.799 (2)	162

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

Acknowledgements

The author thanks Dr J.-M. Gu of Zhejiang University for the data collection.

References

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