Poly[μ₂-aqua-[μ₂-1,1′-(butane-1,4-di­yl)diimidazole]bis­(μ₄-naphthalene-1,4-dicarboxyl­ato)dimanganese(II)]

In the title compound, [Mn₂(C₁₂H₆O₄)₂(C₁₀H₁₄N₄)(H₂O)]_n or [Mn₂(1,4-ndc)₂(L)(H₂O)]_n, where 1,4-ndc is naphthalene-1,4-dicarboxyl­ate and L is 1,1′-(butane-1,4-di­yl)diimidazole, the coordination polyhedron around each Mn^II atom is distorted octa­hedral. The water mol­ecule 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.081
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   293.000
            Value of melting point given =     0.000
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.11 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.13 Ratio

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Some interesting interpenetrated or entangled metal-organic networks with bis(imidazole)-containing ligands have been documented (Yang et al., 2008). But, flexible ligands such as 1,1'-(1,4-butanediyl)bis(imidazole) (L) have not been well explored (Ma et al., 2003). In this work, we used 1,4-naphthalenedicarboxylic acid (1,4-H₂ndc) and L as linkers to obtain a new coordination polymer, [Mn₂(1,4-ndc)₂(L)(H₂O)]. We report here its crystal structure.

In the title compound, each Mn^II atom displays a distorted octahedral coordination sphere, completed by one N atom from one L ligand, four carboxylate O atoms from 1,4-ndc ligand and the O atom of the water molecule (Fig. 1). Both the water molecule and L ligand are situated across a twofold rotation axis. Two adjacent Mn^II atoms are bridged by carboxylate groups of 1,4-ndc ligands and water molecules forming a three- dimensional network containing [Mn₂(1,4-ndc)₂(H₂O)] units. The network is further strengthened by the coordination of L ligands (Fig. 2).

Related literature

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

S2. Experimental

A mixture of 1,4-H₂ndc (0.5 mmol), L (0.5 mmol), NaOH (1 mmol) and MnCl₂^.2H₂O (0.5 mmol) was suspended in 14 ml of deionized water and sealed in a 20-ml Teflon-lined autoclave. Upon heating at 413 K for 3 d, the autoclave was slowly cooled to room temperature. The crystals formed were collected, washed with deionized water and dried.

S3. Refinement

C–bound H atoms were positioned geometrically (C-H = 0.93–0.97 Å) and refined as riding, with U_iso(H) = 1.2U_eq(C). The water H atom was located in a difference Fourier map and refined freely.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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

	Fig. 1. Part of the polymeric structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) 1-x, y, 3/2-z; (ii) 3/2-x, 1/2+y, 3/1-z; (iii) x-1/2, 1/2-y, z-1/2; (iv) -x, y, 1/2-z.
	Fig. 2. View of the three-dimensional framework of the title compound.

Poly[µ₂-aqua-[µ₂-1,1'-(butane-1,4-diyl)diimidazole]bis(µ₄-naphthalene-1,4-dicarboxylato)dimanganese(II)]

Crystal data

[Mn2(C12H6O4)2(C10H14N4)(H2O)]	F(000) = 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 = 1.1–26.1°
b = 14.8887 (18) Å	µ = 0.89 mm^−1
c = 13.9121 (17) Å	T = 293 K
β = 126.319 (1)°	Block, colourless
V = 3068.5 (6) Å^3	0.31 × 0.29 × 0.23 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer	3032 independent reflections
Radiation source: fine-focus sealed tube	2643 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ϕ and ω scans	θmax = 26.1°, θmin = 1.9°
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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 3.0197P] where P = (Fo^2 + 2Fc^2)/3
3032 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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—C15^i	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—O2^ii	2.1535 (14)
C9—C12	1.362 (4)	Mn1—O1W	2.2085 (11)
C9—H9	0.93	O1W—Mn1^ii	2.2085 (11)
C10—C11	1.359 (4)	O1W—H1W1	0.83 (3)
C10—H10	0.93	O4—Mn1^iii	2.2115 (14)
C11—C12	1.401 (4)	O4—Mn1^iv	2.4148 (13)
C11—H11	0.93	Mn1—O2^ii	2.1535 (14)
C12—H12	0.93	Mn1—O4^v	2.2115 (14)
C13—N1	1.323 (3)	Mn1—O4^vi	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—C15^i	114.7 (3)
C3—C2—C8	119.57 (18)	C14—C15—H15A	108.6
C3—C2—C1	119.00 (19)	C15^i—C15—H15A	108.6
C8—C2—C1	121.33 (18)	C14—C15—H15B	108.6
C2—C3—C4	121.3 (2)	C15^i—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—Mn1^ii	133.19 (13)
C9—C8—C7	118.2 (2)	Mn1—O1W—Mn1^ii	118.46 (9)
C2—C8—C7	118.94 (19)	Mn1—O1W—H1W1	101 (2)
C12—C9—C8	120.9 (2)	Mn1^ii—O1W—H1W1	112 (2)
C12—C9—H9	119.5	C6—O4—Mn1^iii	128.35 (12)
C8—C9—H9	119.5	C6—O4—Mn1^iv	123.05 (12)
C11—C10—C7	120.9 (2)	Mn1^iii—O4—Mn1^iv	106.99 (5)
C11—C10—H10	119.6	O1—Mn1—O2^ii	89.34 (6)
C7—C10—H10	119.6	O1—Mn1—O1W	89.50 (6)
C10—C11—C12	120.1 (2)	O2^ii—Mn1—O1W	89.38 (5)
C10—C11—H11	119.9	O1—Mn1—O4^v	91.01 (6)
C12—C11—H11	119.9	O2^ii—Mn1—O4^v	111.20 (5)
C9—C12—C11	120.9 (2)	O1W—Mn1—O4^v	159.42 (5)
C9—C12—H12	119.5	O1—Mn1—N1	174.19 (6)
C11—C12—H12	119.5	O2^ii—Mn1—N1	85.26 (6)
N1—C13—N2	112.1 (2)	O1W—Mn1—N1	88.30 (6)
N1—C13—H13	123.9	O4^v—Mn1—N1	92.93 (6)
N2—C13—H13	123.9	O1—Mn1—O4^vi	93.37 (6)
N2—C14—C15	114.4 (2)	O2^ii—Mn1—O4^vi	174.98 (6)
N2—C14—H14A	108.7	O1W—Mn1—O4^vi	86.42 (4)
C15—C14—H14A	108.7	O4^v—Mn1—O4^vi	73.01 (5)
N2—C14—H14B	108.7	N1—Mn1—O4^vi	91.86 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3^vi	0.83 (3)	1.72 (3)	2.5361 (19)	166 (3)

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