Poly[μ(2)-aqua-[μ(2)-1,1'-(butane-1,4-di-yl)diimidazole]bis-(μ(4)-naphthalene-1,4-dicarboxyl-ato)dimanganese(II)].

In the title compound, [Mn(2)(C(12)H(6)O(4))(2)(C(10)H(14)N(4))(H(2)O)](n) or [Mn(2)(1,4-ndc)(2)(L)(H(2)O)](n), where 1,4-ndc is naphthalene-1,4-dicarboxyl-ate and L is 1,1'-(butane-1,4-di-yl)diimidazole, the coordination polyhedron around each Mn(II) atom is distorted octa-hedral. The water mol-ecule and the L ligand are situated across a twofold rotation axis. The Mn(II) atoms are bridged by 1,4-ndc and L ligands, forming a three-dimensional network. O-H⋯O hydrogen bonds are observed within the network.

Related literature

For general background, see: Ma et al. (2003 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

[Mn2(C12H6O4)2(C10H14N4)(H2O)]

M = 746.48

Monoclinic,

a = 18.386 (2) Å

b = 14.8887 (18) Å

c = 13.9121 (17) Å

β = 126.319 (1)°

V = 3068.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.89 mm−1

T = 293 (2) K

0.31 × 0.29 × 0.23 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.754, T max = 0.814

8475 measured reflections

3032 independent reflections

2643 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.081

S = 1.06

3032 reflections

226 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036787/ci2711sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036787/ci2711Isup2.hkl

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

[Mn2(C12H6O4)2(C10H14N4)(H2O)]	F000 = 1528
Mr = 746.48	Dx = 1.616 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3032 reflections
a = 18.386 (2) Å	θ = 1.1–26.1º
b = 14.8887 (18) Å	µ = 0.89 mm−1
c = 13.9121 (17) Å	T = 293 (2) K
β = 126.319 (1)º	Block, colourless
V = 3068.5 (6) Å3	0.31 × 0.29 × 0.23 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	3032 independent reflections
Radiation source: fine-focus sealed tube	2643 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 293(2) K	θmax = 26.1º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −21→22
Tmin = 0.754, Tmax = 0.814	k = −17→18
8475 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.039P)2 + 3.0197P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3032 reflections	Δρmax = 0.36 e Å−3
226 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
C1	0.62201 (13)	0.35715 (13)	0.80331 (19)	0.0292 (4)
C2	0.69094 (14)	0.28719 (14)	0.82714 (18)	0.0284 (4)
C3	0.78080 (14)	0.30737 (15)	0.90435 (19)	0.0365 (5)
H3	0.7985	0.3593	0.9502	0.044*
C4	0.84703 (15)	0.25114 (16)	0.9159 (2)	0.0380 (5)
H4	0.9076	0.2671	0.9671	0.046*
C5	0.82279 (14)	0.17325 (14)	0.85222 (18)	0.0312 (5)
C6	0.89049 (15)	0.12254 (14)	0.84487 (19)	0.0340 (5)
C7	0.73108 (15)	0.14565 (14)	0.77897 (19)	0.0311 (5)
C8	0.66391 (14)	0.20353 (14)	0.76583 (18)	0.0287 (4)
C9	0.57318 (16)	0.17399 (16)	0.6942 (2)	0.0412 (5)
H9	0.5284	0.2108	0.6844	0.049*
C10	0.70427 (18)	0.06162 (16)	0.7191 (2)	0.0433 (6)
H10	0.7475	0.0238	0.7262	0.052*
C11	0.6163 (2)	0.03575 (17)	0.6515 (3)	0.0547 (7)
H11	0.5998	−0.0196	0.6132	0.066*
C12	0.55052 (19)	0.09235 (19)	0.6395 (3)	0.0562 (7)
H12	0.4905	0.0739	0.5934	0.067*
C13	0.26433 (15)	0.55518 (18)	0.4740 (2)	0.0458 (6)
H13	0.2502	0.5058	0.5011	0.055*
C14	0.12054 (17)	0.6389 (3)	0.3926 (3)	0.0710 (10)
H14A	0.1202	0.6951	0.4277	0.085*
H14B	0.1097	0.5909	0.4298	0.085*
C15	0.04623 (15)	0.6403 (2)	0.2644 (2)	0.0521 (7)
H15A	0.0518	0.5883	0.2273	0.062*
H15B	0.0525	0.6934	0.2295	0.062*
C16	0.25299 (18)	0.68327 (19)	0.3927 (2)	0.0509 (7)
H16	0.2318	0.7383	0.3541	0.061*
C17	0.33284 (16)	0.64368 (16)	0.4330 (2)	0.0420 (6)
H17	0.3763	0.6682	0.4265	0.050*
N1	0.34027 (11)	0.56325 (13)	0.48419 (16)	0.0334 (4)
N2	0.21024 (13)	0.62621 (16)	0.42028 (18)	0.0474 (5)
O1	0.56289 (11)	0.37653 (11)	0.69574 (14)	0.0431 (4)
O2	0.63083 (10)	0.39108 (10)	0.89143 (13)	0.0384 (4)
O1W	0.5000	0.54659 (13)	0.7500	0.0258 (4)
O3	0.88390 (16)	0.13596 (16)	0.75292 (18)	0.0801 (8)
O4	0.94753 (9)	0.07087 (9)	0.92823 (12)	0.0271 (3)
Mn1	0.456815 (18)	0.470697 (19)	0.58778 (3)	0.02220 (10)
H1W1	0.542 (2)	0.578 (2)	0.760 (3)	0.080 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0272 (11)	0.0277 (10)	0.0356 (12)	0.0069 (8)	0.0203 (10)	0.0041 (9)
C2	0.0293 (11)	0.0307 (10)	0.0280 (11)	0.0099 (8)	0.0186 (9)	0.0049 (8)
C3	0.0322 (12)	0.0365 (12)	0.0344 (12)	0.0065 (9)	0.0163 (10)	−0.0075 (9)
C4	0.0250 (11)	0.0478 (13)	0.0333 (12)	0.0089 (10)	0.0129 (10)	−0.0012 (10)
C5	0.0329 (11)	0.0359 (11)	0.0272 (10)	0.0153 (9)	0.0192 (10)	0.0098 (9)
C6	0.0373 (12)	0.0355 (11)	0.0365 (12)	0.0165 (9)	0.0259 (11)	0.0104 (10)
C7	0.0389 (12)	0.0284 (10)	0.0319 (11)	0.0095 (9)	0.0243 (10)	0.0061 (9)
C8	0.0303 (11)	0.0304 (10)	0.0269 (10)	0.0062 (8)	0.0177 (9)	0.0048 (8)
C9	0.0331 (12)	0.0437 (13)	0.0441 (13)	0.0018 (10)	0.0214 (11)	−0.0002 (11)
C10	0.0604 (17)	0.0318 (12)	0.0464 (14)	0.0081 (11)	0.0363 (14)	0.0011 (10)
C11	0.0689 (19)	0.0365 (13)	0.0581 (17)	−0.0120 (13)	0.0373 (16)	−0.0132 (12)
C12	0.0455 (15)	0.0541 (16)	0.0578 (17)	−0.0147 (13)	0.0245 (14)	−0.0098 (14)
C13	0.0282 (12)	0.0585 (15)	0.0465 (14)	0.0064 (11)	0.0197 (11)	0.0183 (12)
C14	0.0301 (14)	0.129 (3)	0.0529 (17)	0.0267 (16)	0.0241 (13)	0.0157 (18)
C15	0.0276 (13)	0.0674 (18)	0.0541 (16)	−0.0057 (12)	0.0204 (12)	−0.0056 (14)
C16	0.0488 (15)	0.0516 (15)	0.0530 (15)	0.0214 (12)	0.0306 (13)	0.0239 (13)
C17	0.0376 (13)	0.0472 (14)	0.0455 (14)	0.0088 (11)	0.0270 (12)	0.0150 (11)
N1	0.0242 (9)	0.0398 (10)	0.0318 (10)	0.0062 (8)	0.0141 (8)	0.0070 (8)
N2	0.0266 (10)	0.0719 (15)	0.0412 (11)	0.0179 (10)	0.0188 (9)	0.0174 (11)
O1	0.0433 (9)	0.0510 (10)	0.0346 (9)	0.0273 (8)	0.0228 (8)	0.0121 (7)
O2	0.0373 (9)	0.0419 (9)	0.0358 (8)	0.0138 (7)	0.0216 (8)	−0.0021 (7)
O1W	0.0245 (11)	0.0252 (10)	0.0319 (11)	0.000	0.0190 (10)	0.000
O3	0.1034 (17)	0.1078 (18)	0.0677 (13)	0.0817 (15)	0.0718 (14)	0.0575 (13)
O4	0.0232 (7)	0.0305 (7)	0.0271 (7)	0.0091 (6)	0.0146 (6)	0.0064 (6)
Mn1	0.01989 (17)	0.02365 (16)	0.02283 (17)	0.00100 (11)	0.01253 (13)	0.00210 (11)

C1—O2	1.245 (2)	C13—H13	0.93
C1—O1	1.256 (2)	C14—N2	1.467 (3)
C1—C2	1.518 (3)	C14—C15	1.470 (4)
C2—C3	1.368 (3)	C14—H14A	0.97
C2—C8	1.423 (3)	C14—H14B	0.97
C3—C4	1.406 (3)	C15—C15i	1.497 (4)
C3—H3	0.93	C15—H15A	0.97
C4—C5	1.364 (3)	C15—H15B	0.97
C4—H4	0.93	C16—C17	1.357 (3)
C5—C7	1.420 (3)	C16—N2	1.358 (3)
C5—C6	1.510 (3)	C16—H16	0.93
C6—O3	1.228 (3)	C17—N1	1.358 (3)
C6—O4	1.263 (2)	C17—H17	0.93
C7—C10	1.420 (3)	Mn1—N1	2.2157 (17)
C7—C8	1.426 (3)	Mn1—O1	2.1343 (15)
C8—C9	1.414 (3)	Mn1—O2ii	2.1535 (14)
C9—C12	1.362 (4)	Mn1—O1W	2.2085 (11)
C9—H9	0.93	O1W—Mn1ii	2.2085 (11)
C10—C11	1.359 (4)	O1W—H1W1	0.83 (3)
C10—H10	0.93	O4—Mn1iii	2.2115 (14)
C11—C12	1.401 (4)	O4—Mn1iv	2.4148 (13)
C11—H11	0.93	Mn1—O2ii	2.1535 (14)
C12—H12	0.93	Mn1—O4v	2.2115 (14)
C13—N1	1.323 (3)	Mn1—O4vi	2.4148 (13)
C13—N2	1.336 (3)
O2—C1—O1	126.60 (18)	C15—C14—H14B	108.7
O2—C1—C2	117.30 (18)	H14A—C14—H14B	107.6
O1—C1—C2	116.07 (18)	C14—C15—C15i	114.7 (3)
C3—C2—C8	119.57 (18)	C14—C15—H15A	108.6
C3—C2—C1	119.00 (19)	C15i—C15—H15A	108.6
C8—C2—C1	121.33 (18)	C14—C15—H15B	108.6
C2—C3—C4	121.3 (2)	C15i—C15—H15B	108.6
C2—C3—H3	119.3	H15A—C15—H15B	107.6
C4—C3—H3	119.3	C17—C16—N2	106.1 (2)
C5—C4—C3	120.3 (2)	C17—C16—H16	127.0
C5—C4—H4	119.9	N2—C16—H16	127.0
C3—C4—H4	119.9	C16—C17—N1	110.4 (2)
C4—C5—C7	120.31 (18)	C16—C17—H17	124.8
C4—C5—C6	120.2 (2)	N1—C17—H17	124.8
C7—C5—C6	118.88 (19)	C13—N1—C17	104.58 (19)
O3—C6—O4	124.86 (19)	C13—N1—Mn1	124.47 (16)
O3—C6—C5	114.36 (18)	C17—N1—Mn1	130.37 (15)
O4—C6—C5	120.78 (18)	C13—N2—C16	106.84 (19)
C5—C7—C10	121.9 (2)	C13—N2—C14	126.7 (2)
C5—C7—C8	119.17 (19)	C16—N2—C14	126.5 (2)
C10—C7—C8	119.0 (2)	C1—O1—Mn1	140.78 (13)
C9—C8—C2	122.82 (19)	C1—O2—Mn1ii	133.19 (13)
C9—C8—C7	118.2 (2)	Mn1—O1W—Mn1ii	118.46 (9)
C2—C8—C7	118.94 (19)	Mn1—O1W—H1W1	101 (2)
C12—C9—C8	120.9 (2)	Mn1ii—O1W—H1W1	112 (2)
C12—C9—H9	119.5	C6—O4—Mn1iii	128.35 (12)
C8—C9—H9	119.5	C6—O4—Mn1iv	123.05 (12)
C11—C10—C7	120.9 (2)	Mn1iii—O4—Mn1iv	106.99 (5)
C11—C10—H10	119.6	O1—Mn1—O2ii	89.34 (6)
C7—C10—H10	119.6	O1—Mn1—O1W	89.50 (6)
C10—C11—C12	120.1 (2)	O2ii—Mn1—O1W	89.38 (5)
C10—C11—H11	119.9	O1—Mn1—O4v	91.01 (6)
C12—C11—H11	119.9	O2ii—Mn1—O4v	111.20 (5)
C9—C12—C11	120.9 (2)	O1W—Mn1—O4v	159.42 (5)
C9—C12—H12	119.5	O1—Mn1—N1	174.19 (6)
C11—C12—H12	119.5	O2ii—Mn1—N1	85.26 (6)
N1—C13—N2	112.1 (2)	O1W—Mn1—N1	88.30 (6)
N1—C13—H13	123.9	O4v—Mn1—N1	92.93 (6)
N2—C13—H13	123.9	O1—Mn1—O4vi	93.37 (6)
N2—C14—C15	114.4 (2)	O2ii—Mn1—O4vi	174.98 (6)
N2—C14—H14A	108.7	O1W—Mn1—O4vi	86.42 (4)
C15—C14—H14A	108.7	O4v—Mn1—O4vi	73.01 (5)
N2—C14—H14B	108.7	N1—Mn1—O4vi	91.86 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3vi	0.83 (3)	1.72 (3)	2.5361 (19)	166 (3)

Table 1

Selected bond lengths (Å)

Mn1—N1	2.2157 (17)
Mn1—O1	2.1343 (15)
Mn1—O1W	2.2085 (11)
Mn1—O2i	2.1535 (14)
Mn1—O4ii	2.2115 (14)
Mn1—O4iii	2.4148 (13)

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

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3iii	0.83 (3)	1.72 (3)	2.5361 (19)	166 (3)

Symmetry code: (iii) .