catena-Poly[[[aqua-(2,2'-bipyridine)manganese(II)]-μ-5-methoxy-iso-phthalato-κO,O':O''] monohydrate].

In the title compound, {[Mn(C(8)H(4)O(4))(C(10)H(8)N(2))(H(2)O)]·H(2)O}(n), the Mn(II) centre is octa-hedrally coordinated by three O atoms from two 5-methoxy-isophthalate (CH(3)O-ip) ligands, a fourth from a coordinated water mol-ecule 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 CH(3)O-ip ligand, forming a helical chain running along a crystallographic 2(1) 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 = 441.29

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.091

S = 1.02

3470 reflections

275 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.29 e Å−3

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.

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

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

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

[Mn(C8H4O4)(C10H8N2)(H2O)]·H2O	F(000) = 908
Mr = 441.29	Dx = 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

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

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(Fo2) + (0.0276P)2 + 0.6024P] where P = (Fo2 + 2Fc2)/3
3470 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 0.26 e Å−3
6 restraints	Δρmin = −0.29 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 > 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
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*

	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)

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)

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···O3iv	0.85 (2)	1.89 (2)	2.726 (3)	171 (3)
O7—H3W···O2v	0.84 (2)	1.90 (2)	2.724 (3)	169 (4)

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) ; (ii) ; (iii) .