Poly[μ(2)-aqua-aqua-(μ(3)-1H-benzimidazole-5,6-dicarboxyl-ato-κN:O:O)manganese(II)].

In the title complex, [Mn(C(9)H(4)N(2)O(4))(H(2)O)(2)](n), the Mn(II) atom is in a distorted octa-hedral coordination completed by one N atom from one 1H-benzimidazole-5,6-dicarboxyl-ate ligand, two O atoms from two different 1H-benzimidazole-5,6-dicarboxyl-ate ligands, and three O atoms from three water mol-ecules. Two bridging water mol-ecules and two bridging carboxyl-ate groups from a 1H-benzimidazole-5,6-dicarboxyl-ate ligand connect two Mn(II) ions into a dimeric structure. In the crystal, extensive inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonding forms a three-dimensional network.

Related literature

For background to 1H-benzimidazole-5,6-dicarboxyl­ate complexes and related structures, see: Yao et al. (2008 ▶); Wei et al. (2009 ▶); Song et al. (2009a ▶,b ▶).

Experimental

Crystal data

[Mn(C9H4N2O4)(H2O)2]

M = 295.11

Monoclinic,

a = 8.8875 (18) Å

b = 9.2079 (18) Å

c = 12.939 (3) Å

β = 97.22 (3)°

V = 1050.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.28 mm−1

T = 293 K

0.29 × 0.26 × 0.25 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.708, T max = 0.740

8122 measured reflections

1888 independent reflections

1792 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.11

1888 reflections

163 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.84 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011979/zb2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011979/zb2004Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C9H4N2O4)(H2O)2]	F(000) = 596
Mr = 295.11	Dx = 1.866 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9020 reflections
a = 8.8875 (18) Å	θ = 3.2–27.5°
b = 9.2079 (18) Å	µ = 1.28 mm−1
c = 12.939 (3) Å	T = 293 K
β = 97.22 (3)°	Block, colorless
V = 1050.5 (4) Å3	0.29 × 0.26 × 0.25 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	1888 independent reflections
Radiation source: fine-focus sealed tube	1792 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 25.2°, θmin = 3.2°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −10→10
Tmin = 0.708, Tmax = 0.740	k = −11→11
8122 measured reflections	l = −15→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0562P)2 + 1.2161P] where P = (Fo2 + 2Fc2)/3
1888 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.71 e Å−3
18 restraints	Δρmin = −0.84 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.6538 (3)	0.9382 (3)	0.9155 (2)	0.0248 (6)
H1	0.5552	0.9678	0.9215	0.030*
N1	0.7164 (2)	0.8221 (3)	0.96244 (19)	0.0229 (5)
O1W	0.52018 (17)	0.5378 (2)	0.88035 (12)	0.0232 (4)
Mn1	0.59756 (4)	0.64549 (4)	1.03462 (3)	0.01916 (18)
C2	0.8810 (3)	0.9343 (3)	0.8676 (2)	0.0222 (6)
N2	0.7455 (3)	1.0094 (3)	0.85830 (19)	0.0253 (5)
H2	0.7241	1.0871	0.8226	0.030*
O2	1.3361 (2)	0.7520 (2)	0.77220 (15)	0.0249 (4)
O2W	0.6154 (2)	0.74283 (19)	1.18596 (14)	0.0364 (5)
C3	0.8628 (3)	0.8183 (3)	0.9340 (2)	0.0204 (5)
O3	1.3671 (2)	0.7185 (2)	0.99961 (16)	0.0247 (4)
C4	0.9821 (3)	0.7226 (3)	0.9624 (2)	0.0229 (6)
H4	0.9724	0.6463	1.0082	0.028*
O4	1.2334 (2)	0.5175 (2)	0.95142 (17)	0.0281 (5)
C5	1.1158 (3)	0.7451 (3)	0.9201 (2)	0.0204 (6)
C6	1.1295 (3)	0.8575 (3)	0.8473 (2)	0.0208 (6)
C7	1.2657 (3)	0.8663 (3)	0.7888 (2)	0.0194 (6)
C8	1.2495 (3)	0.6528 (3)	0.9593 (2)	0.0211 (6)
C13	1.01235 (18)	0.95590 (19)	0.82118 (13)	0.0237 (6)
H13	1.0212	1.0321	0.7752	0.028*
H4W	0.5700	0.8040	1.1451	0.028*
H1W	0.4444	0.5657	0.8400	0.028*
H3W	0.5794	0.6589	1.1754	0.028*
H2W	0.5900	0.5089	0.8473	0.028*
O1	1.2983 (3)	0.9885 (2)	0.75589 (18)	0.0341 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0165 (13)	0.0247 (15)	0.0341 (15)	0.0037 (10)	0.0065 (11)	0.0005 (12)
N1	0.0160 (11)	0.0230 (12)	0.0309 (13)	0.0014 (9)	0.0079 (9)	0.0030 (10)
O1W	0.0217 (9)	0.0265 (10)	0.0230 (9)	0.0043 (8)	0.0091 (7)	0.0005 (8)
Mn1	0.0167 (3)	0.0175 (3)	0.0242 (3)	0.00077 (14)	0.00610 (17)	0.00014 (15)
C2	0.0182 (13)	0.0197 (13)	0.0291 (14)	0.0021 (10)	0.0048 (11)	0.0025 (11)
N2	0.0205 (12)	0.0214 (12)	0.0348 (13)	0.0057 (9)	0.0067 (10)	0.0086 (10)
O2	0.0248 (10)	0.0233 (10)	0.0285 (10)	0.0012 (8)	0.0102 (8)	−0.0021 (8)
O2W	0.0467 (14)	0.0317 (12)	0.0324 (12)	−0.0080 (10)	0.0109 (10)	−0.0085 (9)
C3	0.0183 (9)	0.0208 (9)	0.0225 (9)	0.0002 (8)	0.0047 (8)	0.0010 (8)
O3	0.0175 (10)	0.0255 (11)	0.0314 (10)	0.0030 (8)	0.0044 (8)	−0.0019 (8)
C4	0.0192 (13)	0.0208 (14)	0.0300 (14)	0.0011 (10)	0.0082 (11)	0.0071 (11)
O4	0.0191 (9)	0.0195 (10)	0.0470 (12)	0.0029 (7)	0.0089 (9)	0.0052 (9)
C5	0.0171 (13)	0.0184 (13)	0.0263 (14)	0.0001 (10)	0.0055 (10)	0.0010 (10)
C6	0.0182 (13)	0.0198 (14)	0.0256 (14)	−0.0015 (9)	0.0077 (11)	−0.0005 (10)
C7	0.0183 (13)	0.0180 (13)	0.0228 (13)	−0.0028 (9)	0.0068 (11)	−0.0012 (10)
C8	0.0187 (14)	0.0230 (15)	0.0239 (14)	0.0026 (10)	0.0112 (11)	0.0038 (10)
C13	0.0232 (14)	0.0189 (13)	0.0302 (14)	0.0006 (10)	0.0087 (11)	0.0066 (11)
O1	0.0359 (9)	0.0296 (9)	0.0411 (9)	−0.0028 (7)	0.0212 (7)	0.0013 (7)

C1—N1	1.317 (4)	N2—H2	0.8600
C1—N2	1.339 (4)	O2—C7	1.257 (3)
C1—H1	0.9300	O2W—H4W	0.8407
N1—C3	1.396 (3)	O2W—H3W	0.8411
N1—Mn1	2.209 (2)	C3—C4	1.392 (4)
O1W—Mn1	2.2572 (18)	O3—C8	1.262 (4)
O1W—Mn1i	2.3334 (19)	O3—Mn1iv	2.1495 (19)
O1W—H1W	0.8386	C4—C5	1.384 (4)
O1W—H2W	0.8401	C4—H4	0.9300
Mn1—O4ii	2.115 (2)	O4—C8	1.256 (3)
Mn1—O2W	2.141 (2)	O4—Mn1ii	2.115 (2)
Mn1—O3iii	2.1496 (19)	C5—C6	1.414 (4)
Mn1—O1Wi	2.3334 (19)	C5—C8	1.497 (4)
Mn1—H4W	2.0785	C6—C13	1.390 (3)
Mn1—H3W	1.8533	C6—C7	1.508 (4)
C2—N2	1.381 (3)	C7—O1	1.250 (3)
C2—C3	1.392 (4)	C13—H13	0.9300
C2—C13	1.393 (3)
N1—C1—N2	113.6 (2)	N1—Mn1—H3W	118.2
N1—C1—H1	123.2	O1W—Mn1—H3W	147.6
N2—C1—H1	123.2	O1Wi—Mn1—H3W	59.0
C1—N1—C3	104.6 (2)	H4W—Mn1—H3W	41.0
C1—N1—Mn1	126.53 (18)	N2—C2—C3	105.7 (2)
C3—N1—Mn1	127.15 (18)	N2—C2—C13	131.3 (2)
Mn1—O1W—Mn1i	90.32 (6)	C3—C2—C13	123.0 (2)
Mn1—O1W—H1W	123.2	C1—N2—C2	107.0 (2)
Mn1i—O1W—H1W	98.2	C1—N2—H2	126.5
Mn1—O1W—H2W	115.3	C2—N2—H2	126.5
Mn1i—O1W—H2W	114.5	Mn1—O2W—H4W	74.3
H1W—O1W—H2W	111.5	Mn1—O2W—H3W	58.9
O4ii—Mn1—O2W	104.41 (8)	H4W—O2W—H3W	111.8
O4ii—Mn1—O3iii	152.59 (8)	C2—C3—C4	120.3 (2)
O2W—Mn1—O3iii	91.19 (8)	C2—C3—N1	109.1 (2)
O4ii—Mn1—N1	100.75 (8)	C4—C3—N1	130.6 (3)
O2W—Mn1—N1	95.40 (9)	C8—O3—Mn1iv	130.88 (18)
O3iii—Mn1—N1	100.03 (8)	C5—C4—C3	117.6 (3)
O4ii—Mn1—O1W	84.15 (8)	C5—C4—H4	121.2
O2W—Mn1—O1W	166.37 (7)	C3—C4—H4	121.2
O3iii—Mn1—O1W	76.97 (7)	C8—O4—Mn1ii	128.63 (18)
N1—Mn1—O1W	93.33 (8)	C4—C5—C6	121.5 (2)
O4ii—Mn1—O1Wi	78.58 (7)	C4—C5—C8	117.7 (2)
O2W—Mn1—O1Wi	81.81 (7)	C6—C5—C8	120.6 (2)
O3iii—Mn1—O1Wi	81.59 (7)	C13—C6—C5	121.0 (2)
N1—Mn1—O1Wi	176.83 (8)	C13—C6—C7	117.8 (2)
O1W—Mn1—O1Wi	89.68 (6)	C5—C6—C7	121.0 (2)
O4ii—Mn1—H4W	125.7	O1—C7—O2	123.6 (3)
O2W—Mn1—H4W	22.9	O1—C7—C6	117.1 (2)
O3iii—Mn1—H4W	74.5	O2—C7—C6	119.3 (2)
N1—Mn1—H4W	83.0	O4—C8—O3	126.1 (3)
O1W—Mn1—H4W	150.1	O4—C8—C5	117.2 (2)
O1Wi—Mn1—H4W	94.9	O3—C8—C5	116.7 (2)
O4ii—Mn1—H3W	96.4	C6—C13—C2	116.4 (2)
O2W—Mn1—H3W	22.9	C6—C13—H13	121.8
O3iii—Mn1—H3W	89.3	C2—C13—H13	121.8

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2v	0.86	1.98	2.839 (3)	174
O2W—H4W···O3iii	0.84	2.56	3.065 (3)	120
O1W—H1W···O2iii	0.84	2.10	2.819 (3)	143
O2W—H3W···O1Wi	0.84	2.10	2.934 (3)	169
O1W—H2W···O1vi	0.84	1.77	2.575 (3)	160
C4—H4···O4ii	0.93	2.48	3.216 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	1.98	2.839 (3)	174
O2W—H4W⋯O3ii	0.84	2.56	3.065 (3)	120
O1W—H1W⋯O2ii	0.84	2.10	2.819 (3)	143
O2W—H3W⋯O1Wiii	0.84	2.10	2.934 (3)	169
O1W—H2W⋯O1iv	0.84	1.77	2.575 (3)	160
C4—H4⋯O4v	0.93	2.48	3.216 (3)	136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .