A two-dimensional network con­taining an –Mn—O—C—O—Mn– chain: poly[diaqua[1,2-bis(pyridin-4-yl)ethylene][μ3-3-carboxy-5-(carboxylatomethoxy)benzoato]manganese(II)]

Lei, Y.-Q.; Wang, G.-H.

doi:10.1107/S0108270113025377

A two-dimensional network containing an –Mn—O—C—O—Mn– chain: poly[diaqua[1,2-bis(pyridin-4-yl)ethylene][μ₃-3-carboxy-5-(carboxylatomethoxy)benzoato]manganese(II)]

In the title compound, [Mn(C₁₀H₆O₇)(C₁₂H₁₀N₂)(H₂O)₂]_n or [Mn(HOABDC)(bpe)(H₂O)₂]_n [H₃OABDC is 5-(carboxymethoxy)isophthalic acid and bpe is 1,2-bis(pyridin-4-yl)ethylene], each Mn^II cation is at the centre of a distorted octahedron formed by three carboxylate O atoms from three different HOABDC²⁻ ligands, one pyridyl N atom from the terminal bpe ligand and two water molecules. The flexible oxyacetate group bound to a methylene C atom of the HOABDC²⁻ ligand links the Mn^II centres into –Mn—O—C—O—Mn– chains, and the carboxylate group bound directly to the benzene ring extends the chains into two-dimensional layers which lie parallel to the (010) plane and present herringbone patterns. Intermolecular O—H

N and C—H

O hydrogen bonds connect the layers into a three-dimensional supramolecular structure.

Keywords: crystal structure; two-dimensional polymeric structures; manganese compounds; 5-(carboxymethoxy)isophthalic acid.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113025377/fn3147sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270113025377/fn3147Isup2.hkl Contains datablock I

CCDC reference: 960924

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Poly[diaqua[1,2-bis(pyridin-4-yl)ethylene][µ₃-3-carboxy-5-(carboxylatomethoxy)benzoato]manganese(II)] top

Crystal data top

[Mn(C₁₀H₆O₇)(C₁₂H₁₀N₂)(H₂O)₂]	F(000) = 1052
M_r = 511.34	D_x = 1.565 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1133 reflections
a = 9.092 (4) Å	θ = 1.4–26.1°
b = 29.484 (12) Å	µ = 0.67 mm⁻¹
c = 9.093 (4) Å	T = 293 K
β = 117.04 (5)°	Plate, red
V = 2170.8 (15) Å³	0.11 × 0.10 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4273 independent reflections
Radiation source: sealed tube	2759 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
φ and ω scans	θ_max = 26.1°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.930, T_max = 0.974	k = −28→36
12116 measured reflections	l = −11→10

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0469P)²] where P = (F_o² + 2F_c²)/3
4273 reflections	(Δ/σ)_max < 0.001
327 parameters	Δρ_max = 0.42 e Å⁻³
7 restraints	Δρ_min = −0.29 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Mn1	0.08054 (8)	0.77496 (2)	0.17702 (8)	0.0292 (2)
N1	0.0985 (5)	0.82429 (12)	0.3769 (5)	0.0363 (10)
N2	0.2457 (6)	1.00602 (14)	1.2814 (5)	0.0502 (12)
O1	0.2343 (4)	0.72909 (10)	0.3640 (4)	0.0422 (8)
O2	0.4275 (4)	0.67763 (10)	0.4928 (4)	0.0420 (9)
O3	−0.1982 (4)	0.72026 (11)	0.4508 (4)	0.0455 (9)
O4	−0.1964 (4)	0.69710 (10)	0.6838 (4)	0.0379 (8)
O5	0.1668 (5)	0.56862 (13)	0.9914 (5)	0.0608 (11)
H5	0.207 (9)	0.5450 (16)	1.053 (8)	0.14 (3)*
O6	0.2656 (5)	0.52384 (14)	0.8624 (5)	0.0798 (14)
O7	0.1871 (4)	0.61208 (10)	0.3631 (4)	0.0423 (9)
C1	0.2901 (6)	0.68908 (16)	0.3824 (6)	0.0339 (11)
C2	0.1810 (6)	0.65122 (14)	0.2664 (6)	0.0345 (11)
H2A	0.0680	0.6618	0.2062	0.041*
H2B	0.2207	0.6434	0.1871	0.041*
C3	0.1330 (6)	0.61900 (15)	0.4797 (6)	0.0341 (11)
C4	0.0275 (5)	0.65374 (15)	0.4728 (6)	0.0345 (11)
H4	−0.0090	0.6743	0.3857	0.041*
C5	−0.0241 (5)	0.65832 (15)	0.5929 (5)	0.0298 (10)
C6	−0.1483 (5)	0.69491 (15)	0.5735 (6)	0.0317 (11)
C7	0.0334 (5)	0.62846 (15)	0.7259 (6)	0.0358 (12)
H7	0.0015	0.6321	0.8090	0.043*
C8	0.1386 (6)	0.59313 (15)	0.7347 (6)	0.0366 (12)
C9	0.1977 (7)	0.55817 (18)	0.8694 (7)	0.0496 (14)
C10	0.1859 (6)	0.58831 (15)	0.6106 (6)	0.0397 (12)
H10	0.2538	0.5643	0.6145	0.048*
C11	0.1988 (7)	0.85953 (18)	0.4142 (7)	0.0555 (16)
H11	0.2571	0.8636	0.3536	0.067*
C12	0.2233 (7)	0.89050 (18)	0.5358 (7)	0.0568 (16)
H12	0.2956	0.9146	0.5542	0.068*
C13	0.1415 (6)	0.88614 (15)	0.6306 (6)	0.0392 (12)
C14	0.0361 (7)	0.84947 (19)	0.5929 (7)	0.0605 (17)
H14	−0.0223	0.8442	0.6528	0.073*
C15	0.0178 (7)	0.82062 (19)	0.4663 (7)	0.0568 (16)
H15	−0.0568	0.7968	0.4419	0.068*
C16	0.1737 (6)	0.91804 (16)	0.7660 (7)	0.0473 (14)
H16	0.2323	0.9441	0.7684	0.057*
C17	0.1294 (6)	0.91401 (17)	0.8833 (6)	0.0440 (13)
H17	0.0656	0.8889	0.8794	0.053*
C18	0.1720 (6)	0.94565 (15)	1.0201 (6)	0.0377 (12)
C19	0.2978 (6)	0.97689 (16)	1.0661 (6)	0.0471 (14)
H19	0.3606	0.9784	1.0092	0.056*
C20	0.3306 (7)	1.00578 (17)	1.1957 (7)	0.0495 (14)
H20	0.4172	1.0263	1.2249	0.059*
C21	0.1256 (7)	0.97604 (18)	1.2396 (7)	0.0531 (15)
H21	0.0647	0.9756	1.2986	0.064*
C22	0.0855 (7)	0.94500 (17)	1.1114 (7)	0.0510 (14)
H22	0.0012	0.9240	1.0876	0.061*
O1W	0.0814 (4)	0.72696 (12)	−0.0097 (4)	0.0408 (8)
H1WA	0.143 (4)	0.7384 (15)	−0.048 (5)	0.044 (16)*
H1WB	−0.008 (3)	0.7231 (14)	−0.094 (4)	0.035 (15)*
O2W	−0.1337 (4)	0.74191 (14)	0.1860 (5)	0.0479 (10)
H2WA	−0.215 (4)	0.7461 (19)	0.096 (3)	0.07 (2)*
H2WB	−0.163 (5)	0.7363 (17)	0.256 (4)	0.059 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0318 (4)	0.0308 (4)	0.0269 (4)	0.0002 (3)	0.0149 (3)	−0.0007 (3)
N1	0.046 (2)	0.031 (2)	0.034 (2)	0.0023 (19)	0.021 (2)	−0.0033 (18)
N2	0.065 (3)	0.043 (3)	0.039 (3)	0.000 (2)	0.021 (2)	−0.009 (2)
O1	0.052 (2)	0.0298 (19)	0.035 (2)	0.0057 (16)	0.0119 (17)	0.0001 (15)
O2	0.039 (2)	0.038 (2)	0.040 (2)	0.0047 (16)	0.0092 (17)	−0.0025 (16)
O3	0.056 (2)	0.050 (2)	0.044 (2)	0.0200 (18)	0.0339 (18)	0.0194 (18)
O4	0.0376 (19)	0.050 (2)	0.0328 (19)	0.0088 (16)	0.0217 (16)	0.0079 (16)
O5	0.100 (3)	0.044 (2)	0.047 (3)	0.015 (2)	0.042 (2)	0.013 (2)
O6	0.122 (4)	0.058 (3)	0.085 (3)	0.049 (3)	0.069 (3)	0.030 (2)
O7	0.067 (2)	0.0309 (19)	0.048 (2)	0.0032 (17)	0.043 (2)	0.0003 (16)
C1	0.042 (3)	0.036 (3)	0.028 (3)	−0.004 (2)	0.019 (2)	−0.005 (2)
C2	0.039 (3)	0.035 (3)	0.032 (3)	−0.001 (2)	0.018 (2)	−0.001 (2)
C3	0.044 (3)	0.025 (2)	0.040 (3)	−0.004 (2)	0.024 (3)	−0.004 (2)
C4	0.041 (3)	0.032 (3)	0.034 (3)	0.001 (2)	0.021 (2)	0.004 (2)
C5	0.032 (3)	0.032 (3)	0.025 (3)	0.000 (2)	0.012 (2)	0.002 (2)
C6	0.029 (3)	0.032 (3)	0.034 (3)	−0.002 (2)	0.015 (2)	0.001 (2)
C7	0.042 (3)	0.038 (3)	0.033 (3)	−0.001 (2)	0.022 (3)	−0.001 (2)
C8	0.047 (3)	0.029 (3)	0.038 (3)	0.005 (2)	0.023 (3)	0.004 (2)
C9	0.063 (4)	0.046 (3)	0.044 (4)	0.008 (3)	0.028 (3)	0.007 (3)
C10	0.050 (3)	0.028 (3)	0.048 (3)	0.006 (2)	0.028 (3)	−0.001 (2)
C11	0.081 (4)	0.043 (3)	0.061 (4)	−0.010 (3)	0.049 (4)	−0.008 (3)
C12	0.081 (4)	0.042 (3)	0.062 (4)	−0.026 (3)	0.045 (4)	−0.016 (3)
C13	0.044 (3)	0.033 (3)	0.039 (3)	0.003 (2)	0.017 (3)	−0.004 (2)
C14	0.067 (4)	0.067 (4)	0.071 (4)	−0.017 (3)	0.051 (4)	−0.028 (3)
C15	0.059 (4)	0.059 (4)	0.066 (4)	−0.026 (3)	0.041 (3)	−0.028 (3)
C16	0.061 (4)	0.033 (3)	0.051 (4)	−0.007 (3)	0.028 (3)	−0.010 (2)
C17	0.047 (3)	0.043 (3)	0.047 (3)	−0.002 (3)	0.025 (3)	−0.010 (3)
C18	0.045 (3)	0.028 (3)	0.037 (3)	0.002 (2)	0.016 (3)	−0.006 (2)
C19	0.059 (4)	0.038 (3)	0.052 (4)	0.002 (3)	0.032 (3)	−0.007 (3)
C20	0.065 (4)	0.035 (3)	0.051 (4)	−0.006 (3)	0.029 (3)	−0.006 (3)
C21	0.071 (4)	0.053 (3)	0.049 (4)	0.007 (3)	0.039 (3)	−0.004 (3)
C22	0.057 (4)	0.044 (3)	0.058 (4)	−0.004 (3)	0.031 (3)	−0.011 (3)
O1W	0.039 (2)	0.046 (2)	0.038 (2)	−0.0059 (19)	0.018 (2)	−0.0059 (18)
O2W	0.043 (2)	0.070 (3)	0.031 (2)	−0.0070 (19)	0.017 (2)	0.008 (2)

Geometric parameters (Å, º) top

Mn1—O1	2.124 (3)	C7—C8	1.392 (6)
Mn1—O2ⁱ	2.139 (3)	C7—H7	0.9300
Mn1—O4ⁱⁱ	2.164 (3)	C8—C10	1.386 (6)
Mn1—O2W	2.212 (4)	C8—C9	1.501 (7)
Mn1—O1W	2.213 (3)	C10—H10	0.9300
Mn1—N1	2.275 (4)	C11—C12	1.372 (7)
N1—C11	1.321 (6)	C11—H11	0.9300
N1—C15	1.323 (6)	C12—C13	1.377 (7)
N2—C21	1.320 (6)	C12—H12	0.9300
N2—C20	1.323 (6)	C13—C14	1.380 (6)
O1—C1	1.265 (5)	C13—C16	1.469 (6)
O2—C1	1.242 (5)	C14—C15	1.380 (7)
O2—Mn1ⁱⁱⁱ	2.139 (3)	C14—H14	0.9300
O3—C6	1.245 (5)	C15—H15	0.9300
O4—C6	1.265 (5)	C16—C17	1.305 (7)
O4—Mn1^iv	2.164 (3)	C16—H16	0.9300
O5—C9	1.299 (6)	C17—C18	1.459 (6)
O5—H5	0.86 (2)	C17—H17	0.9300
O6—C9	1.202 (6)	C18—C19	1.377 (6)
O7—C3	1.372 (5)	C18—C22	1.379 (7)
O7—C2	1.436 (5)	C19—C20	1.372 (7)
C1—C2	1.546 (6)	C19—H19	0.9300
C2—H2A	0.9700	C20—H20	0.9300
C2—H2B	0.9700	C21—C22	1.394 (7)
C3—C4	1.385 (6)	C21—H21	0.9300
C3—C10	1.394 (6)	C22—H22	0.9300
C4—C5	1.377 (6)	O1W—H1WA	0.848 (18)
C4—H4	0.9300	O1W—H1WB	0.835 (18)
C5—C7	1.392 (6)	O2W—H2WA	0.824 (19)
C5—C6	1.513 (6)	O2W—H2WB	0.815 (19)

O1—Mn1—O2ⁱ	178.71 (12)	C7—C8—C9	122.9 (4)
O1—Mn1—O4ⁱⁱ	87.27 (13)	O6—C9—O5	124.1 (5)
O2ⁱ—Mn1—O4ⁱⁱ	92.36 (12)	O6—C9—C8	122.5 (5)
O1—Mn1—O2W	87.71 (14)	O5—C9—C8	113.4 (5)
O2ⁱ—Mn1—O2W	92.67 (14)	C8—C10—C3	120.9 (4)
O4ⁱⁱ—Mn1—O2W	174.97 (14)	C8—C10—H10	119.5
O1—Mn1—O1W	88.64 (13)	C3—C10—H10	119.5
O2ⁱ—Mn1—O1W	92.57 (13)	N1—C11—C12	124.8 (5)
O4ⁱⁱ—Mn1—O1W	86.29 (13)	N1—C11—H11	117.6
O2W—Mn1—O1W	93.24 (15)	C12—C11—H11	117.6
O1—Mn1—N1	89.17 (13)	C11—C12—C13	120.4 (5)
O2ⁱ—Mn1—N1	89.59 (13)	C11—C12—H12	119.8
O4ⁱⁱ—Mn1—N1	90.45 (13)	C13—C12—H12	119.8
O2W—Mn1—N1	89.82 (15)	C12—C13—C14	115.4 (5)
O1W—Mn1—N1	176.16 (14)	C12—C13—C16	120.4 (5)
C11—N1—C15	114.7 (4)	C14—C13—C16	124.1 (5)
C11—N1—Mn1	119.9 (3)	C15—C14—C13	119.8 (5)
C15—N1—Mn1	125.4 (3)	C15—C14—H14	120.1
C21—N2—C20	117.1 (5)	C13—C14—H14	120.1
C1—O1—Mn1	141.1 (3)	N1—C15—C14	124.9 (5)
C1—O2—Mn1ⁱⁱⁱ	120.8 (3)	N1—C15—H15	117.6
C6—O4—Mn1^iv	130.8 (3)	C14—C15—H15	117.6
C9—O5—H5	100 (5)	C17—C16—C13	127.5 (5)
C3—O7—C2	115.2 (3)	C17—C16—H16	116.3
O2—C1—O1	123.8 (4)	C13—C16—H16	116.3
O2—C1—C2	116.9 (4)	C16—C17—C18	125.3 (5)
O1—C1—C2	119.3 (4)	C16—C17—H17	117.4
O7—C2—C1	109.2 (4)	C18—C17—H17	117.4
O7—C2—H2A	109.8	C19—C18—C22	116.6 (5)
C1—C2—H2A	109.8	C19—C18—C17	123.3 (5)
O7—C2—H2B	109.8	C22—C18—C17	120.1 (5)
C1—C2—H2B	109.8	C20—C19—C18	120.2 (5)
H2A—C2—H2B	108.3	C20—C19—H19	119.9
O7—C3—C4	124.0 (4)	C18—C19—H19	119.9
O7—C3—C10	117.2 (4)	N2—C20—C19	123.5 (5)
C4—C3—C10	118.8 (4)	N2—C20—H20	118.3
C5—C4—C3	121.0 (4)	C19—C20—H20	118.3
C5—C4—H4	119.5	N2—C21—C22	123.2 (5)
C3—C4—H4	119.5	N2—C21—H21	118.4
C4—C5—C7	119.9 (4)	C22—C21—H21	118.4
C4—C5—C6	118.9 (4)	C18—C22—C21	119.4 (5)
C7—C5—C6	121.2 (4)	C18—C22—H22	120.3
O3—C6—O4	124.3 (4)	C21—C22—H22	120.3
O3—C6—C5	118.8 (4)	Mn1—O1W—H1WA	107 (3)
O4—C6—C5	116.9 (4)	Mn1—O1W—H1WB	117 (3)
C5—C7—C8	120.0 (4)	H1WA—O1W—H1WB	103 (3)
C5—C7—H7	120.0	Mn1—O2W—H2WA	108 (3)
C8—C7—H7	120.0	Mn1—O2W—H2WB	137 (3)
C10—C8—C7	119.3 (4)	H2WA—O2W—H2WB	110 (3)
C10—C8—C9	117.7 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2^v	0.86 (2)	1.78 (1)	2.61 (2)	159 (2)
C20—H20···O7^vi	0.93	2.69	3.171 (6)	112 (3)
O1W—H1WA···O3ⁱⁱ	0.85 (2)	1.90 (2)	2.687 (18)	154 (2)
O1W—H1WB···O4^vii	0.84 (2)	2.11 (2)	2.919 (19)	163 (2)
O2W—H2WA···O1ⁱ	0.82 (2)	2.08 (2)	2.747 (19)	138 (2)
O2W—H2WB···O3	0.82 (2)	1.99 (2)	2.799 (19)	171 (3)

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x+1/2, −y+3/2, z−1/2; (v) −x+1/2, y−1/2, −z+5/2; (vi) −x+1/2, y+1/2, −z+3/2; (vii) x, y, z−1.

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A two-dimensional network con­taining an –Mn—O—C—O—Mn– chain: poly[diaqua[1,2-bis(pyridin-4-yl)ethylene][μ3-3-carboxy-5-(carboxylatomethoxy)benzoato]manganese(II)]

Supporting information

A two-dimensional network containing an –Mn—O—C—O—Mn– chain: poly[diaqua[1,2-bis(pyridin-4-yl)ethylene][μ₃-3-carboxy-5-(carboxylatomethoxy)benzoato]manganese(II)]