Poly[[[μ(2)-1,1'-(butane-1,4-di-yl)bis-(1H-imidazole)-κN:N](μ(2)-2,6-di-methyl-pyridine-3,5-dicarboxyl-ato-κO:O)zinc] dihydrate].

In the title coordination polymer, {[Zn(C(9)H(7)NO(4))(C(10)H(14)N(4))]·2H(2)O}(n), the Zn(II) ion displays a distorted tetra-hedral geometry with two imidazole N atoms from two 1,1'-(butane-1,4-di-yl)bis-(imidazole) (bbi) ligands and two carboxyl-ate O atoms from two 2,6-dimethyl-pyridine-3,5-dicarboxyl-ate (dpdc) ligands. The bbi and dpdc ligands bridge the Zn(II) ions, forming layers parallel to (011). O-H⋯O and O-H⋯N hydrogen bonds and π-π inter-actions between the imidazole rings [centroid-centroid distance = 3.807 (5) Å] connect the layers. Two of the three uncoordinated water mol-ecules are disordered, each over two 0.25-occupancy positions.

Related literature

For transition metal complexes derived from 2,6-dimethyl­pyridine-3,5-dicarb­oxy­lic acid, see: Chen et al. (2009 ▶); Huang et al. (2008 ▶); Zhang et al. (2008a ▶); Zhou et al. (2009 ▶). For metal complexes derived from 1,1′-(butane-1,4-di­yl)bis­(imidazole) and carb­oxy­lic acids, see: Lan et al. (2008 ▶); Tian et al. (2009 ▶); Zhang et al. (2008b ▶).

Experimental

Crystal data

[Zn(C9H7NO4)(C10H14N4)]·2H2O

M = 484.82

Orthorhombic,

a = 17.8088 (12) Å

b = 9.4003 (4) Å

c = 15.5798 (8) Å

V = 2608.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.98 mm−1

T = 293 K

0.22 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.807, T max = 0.823

14228 measured reflections

4717 independent reflections

3753 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.175

S = 1.03

4717 reflections

315 parameters

36 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.64 e Å−3

Absolute structure: Flack (1983 ▶), 2186 Friedel pairs

Flack parameter: 0.03 (2)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039481/hy2452sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039481/hy2452Isup2.hkl

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

[Zn(C9H7NO4)(C10H14N4)]·2H2O	Dx = 1.234 Mg m−3
Mr = 484.82	Melting point: not measured K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4717 reflections
a = 17.8088 (12) Å	θ = 2.3–25.5°
b = 9.4003 (4) Å	µ = 0.98 mm−1
c = 15.5798 (8) Å	T = 293 K
V = 2608.2 (2) Å3	Block, colorless
Z = 4	0.22 × 0.21 × 0.20 mm
F(000) = 1008

Bruker SMART APEX CCD diffractometer	4717 independent reflections
Radiation source: fine-focus sealed tube	3753 reflections with I > 2σ(I)
graphite	Rint = 0.087
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→21
Tmin = 0.807, Tmax = 0.823	k = −11→11
14228 measured reflections	l = −18→18

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)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.175	w = 1/[σ2(Fo2) + (0.1192P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.042
4717 reflections	Δρmax = 0.67 e Å−3
315 parameters	Δρmin = −0.64 e Å−3
36 restraints	Absolute structure: Flack (1983), 2186 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (2)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.73885 (3)	0.97189 (5)	0.87767 (6)	0.0381 (2)
O1	0.6630 (2)	0.8258 (4)	0.8567 (3)	0.0560 (12)
O2	0.7521 (2)	0.6656 (5)	0.8691 (6)	0.0684 (15)
O3	0.5991 (3)	0.1007 (5)	0.9535 (4)	0.0695 (14)
O4	0.6934 (2)	0.1619 (3)	0.8694 (3)	0.0467 (9)
C3	0.6499 (2)	0.4454 (4)	0.8818 (5)	0.0351 (10)
H3	0.7012	0.4269	0.8817	0.080*
N2	0.8088 (3)	0.9860 (6)	0.7781 (4)	0.0429 (13)
N3	0.8753 (3)	0.9276 (6)	0.6618 (4)	0.0522 (13)
N4	1.2098 (4)	1.0326 (6)	0.4941 (4)	0.0477 (15)
N5	1.1556 (4)	0.9499 (7)	0.6067 (3)	0.0527 (16)
C2	0.6262 (3)	0.5836 (5)	0.8704 (4)	0.0362 (10)
C1	0.5488 (2)	0.6115 (5)	0.8722 (4)	0.0362 (10)
N1	0.5019 (2)	0.4987 (4)	0.8838 (6)	0.0395 (10)
C5	0.5237 (3)	0.3608 (6)	0.8968 (3)	0.0381 (13)
C4	0.5999 (3)	0.3304 (5)	0.8935 (3)	0.0363 (13)
C6	0.6854 (3)	0.6980 (5)	0.8651 (4)	0.0383 (12)
C7	0.6308 (3)	0.1830 (5)	0.9067 (3)	0.0372 (12)
C8	0.5117 (3)	0.7510 (6)	0.8585 (5)	0.0523 (16)
H8A	0.5160	0.7777	0.7992	0.080*
H8B	0.5354	0.8218	0.8937	0.080*
H8C	0.4596	0.7439	0.8738	0.080*
C9	0.4619 (4)	0.2569 (7)	0.9113 (5)	0.0599 (18)
H9A	0.4456	0.2623	0.9700	0.080*
H9B	0.4796	0.1625	0.8993	0.080*
H9C	0.4206	0.2789	0.8740	0.080*
C10	0.8374 (4)	0.8823 (7)	0.7308 (4)	0.0470 (15)
H10	0.8318	0.7865	0.7444	0.080*
C11	0.8304 (5)	1.1069 (9)	0.7376 (5)	0.065 (2)
H11	0.8187	1.1980	0.7567	0.080*
C12	0.8718 (5)	1.0785 (10)	0.6648 (6)	0.073 (2)
H12	0.8927	1.1432	0.6264	0.080*
C13	0.9116 (4)	0.8468 (8)	0.5972 (4)	0.0553 (16)
H13A	0.8888	0.8685	0.5422	0.080*
H13B	0.9035	0.7465	0.6086	0.080*
C14	0.9961 (4)	0.8745 (8)	0.5913 (4)	0.0560 (16)
H14A	1.0183	0.8045	0.5532	0.080*
H14B	1.0041	0.9675	0.5659	0.080*
C15	1.0364 (4)	0.8687 (9)	0.6769 (4)	0.0663 (19)
H15A	1.0157	0.7917	0.7109	0.080*
H15B	1.0277	0.9569	0.7076	0.080*
C16	1.1211 (4)	0.8462 (11)	0.6664 (5)	0.080 (3)
H16A	1.1451	0.8545	0.7221	0.080*
H16B	1.1301	0.7507	0.6452	0.080*
C17	1.1862 (5)	0.9177 (9)	0.5306 (5)	0.060 (2)
H17	1.1900	0.8266	0.5077	0.080*
C18	1.1924 (4)	1.1407 (8)	0.5463 (4)	0.0531 (16)
H18	1.2017	1.2365	0.5358	0.080*
C19	1.1601 (4)	1.0882 (12)	0.6143 (5)	0.069 (2)
H19	1.1429	1.1408	0.6609	0.080*
O1W	0.3529 (5)	0.5563 (7)	0.9086 (4)	0.0930 (19)
O3W	0.7170 (19)	0.455 (3)	1.0985 (19)	0.094 (7)	0.25
O3W'	0.670 (3)	0.304 (5)	1.064 (3)	0.166 (14)	0.25
O2W'	0.9930 (11)	0.4765 (19)	1.0714 (12)	0.053 (4)	0.25
O2W	0.9724 (18)	0.538 (3)	1.1357 (19)	0.091 (7)	0.25
H1B	0.320 (2)	0.488 (4)	0.910 (3)	0.080*
H1A	0.3963 (11)	0.515 (6)	0.916 (4)	0.080*

	U11	U22	U33	U12	U13	U23
Zn1	0.0316 (3)	0.0328 (3)	0.0500 (3)	−0.0002 (2)	0.0009 (4)	0.0007 (5)
O1	0.044 (2)	0.0301 (18)	0.094 (4)	−0.0058 (15)	−0.003 (2)	0.003 (2)
O2	0.037 (2)	0.042 (2)	0.126 (5)	−0.0053 (15)	0.003 (3)	0.012 (4)
O3	0.070 (3)	0.048 (3)	0.091 (3)	0.011 (2)	0.024 (3)	0.023 (3)
O4	0.0391 (19)	0.0318 (16)	0.069 (2)	0.0063 (13)	0.002 (2)	0.005 (2)
C3	0.032 (2)	0.033 (2)	0.040 (2)	−0.0028 (17)	0.009 (3)	0.005 (3)
N2	0.034 (3)	0.045 (3)	0.050 (3)	0.003 (2)	−0.002 (2)	0.001 (2)
N3	0.029 (3)	0.062 (3)	0.066 (3)	0.002 (3)	0.004 (2)	0.012 (3)
N4	0.037 (3)	0.054 (3)	0.052 (3)	0.000 (2)	0.001 (2)	0.002 (3)
N5	0.046 (3)	0.072 (4)	0.041 (3)	0.002 (3)	0.002 (2)	0.008 (3)
C2	0.036 (2)	0.034 (2)	0.039 (3)	−0.0024 (19)	0.005 (3)	0.004 (3)
C1	0.031 (2)	0.037 (2)	0.041 (2)	0.0024 (18)	0.006 (3)	0.009 (3)
N1	0.035 (2)	0.036 (2)	0.047 (3)	−0.0004 (15)	−0.007 (3)	−0.004 (2)
C5	0.028 (2)	0.042 (3)	0.045 (4)	−0.008 (2)	−0.001 (2)	0.002 (2)
C4	0.035 (3)	0.028 (2)	0.046 (4)	0.0025 (19)	0.005 (2)	0.003 (2)
C6	0.038 (3)	0.030 (2)	0.048 (3)	−0.0060 (19)	0.004 (2)	−0.001 (2)
C7	0.040 (3)	0.030 (3)	0.042 (3)	−0.002 (2)	0.004 (2)	0.004 (2)
C8	0.039 (3)	0.038 (3)	0.080 (5)	0.003 (2)	−0.002 (3)	0.001 (3)
C9	0.040 (3)	0.047 (3)	0.092 (5)	−0.014 (3)	0.002 (3)	0.008 (3)
C10	0.040 (4)	0.046 (3)	0.055 (3)	−0.001 (3)	−0.004 (3)	0.008 (3)
C11	0.068 (5)	0.050 (4)	0.076 (5)	0.001 (4)	0.035 (4)	0.012 (4)
C12	0.076 (6)	0.063 (5)	0.081 (5)	−0.005 (5)	0.015 (4)	0.002 (4)
C13	0.048 (4)	0.071 (4)	0.047 (3)	0.000 (3)	0.007 (3)	−0.002 (3)
C14	0.040 (3)	0.078 (5)	0.050 (3)	0.004 (3)	0.009 (3)	0.010 (3)
C15	0.051 (4)	0.099 (6)	0.049 (4)	−0.002 (4)	0.004 (3)	0.014 (4)
C16	0.048 (4)	0.125 (8)	0.066 (4)	0.001 (4)	0.005 (3)	0.038 (5)
C17	0.056 (4)	0.062 (5)	0.063 (4)	0.022 (4)	0.006 (3)	0.007 (4)
C18	0.048 (4)	0.059 (4)	0.052 (3)	0.009 (3)	0.005 (3)	−0.013 (3)
C19	0.041 (4)	0.102 (7)	0.063 (5)	−0.002 (5)	0.008 (3)	−0.012 (4)
O1W	0.090 (2)	0.092 (2)	0.097 (2)	−0.0007 (10)	0.0000 (10)	−0.0017 (10)
O3W	0.094 (7)	0.094 (7)	0.093 (7)	0.0002 (10)	−0.0002 (10)	0.0003 (10)
O3W'	0.166 (14)	0.166 (14)	0.166 (14)	0.0000 (10)	0.0000 (10)	0.0001 (10)
O2W'	0.053 (4)	0.053 (4)	0.053 (4)	0.0006 (10)	0.0003 (10)	−0.0006 (10)
O2W	0.092 (7)	0.091 (7)	0.092 (7)	0.0001 (10)	0.0002 (10)	0.0001 (10)

Zn1—O1	1.954 (4)	C4—C7	1.505 (7)
Zn1—O4i	1.965 (3)	C8—H8A	0.9600
Zn1—N2	1.994 (6)	C8—H8B	0.9600
Zn1—N4ii	2.032 (6)	C8—H8C	0.9600
O1—C6	1.272 (6)	C9—H9A	0.9600
O2—C6	1.228 (7)	C9—H9B	0.9600
O3—C7	1.204 (7)	C9—H9C	0.9600
O4—C7	1.273 (7)	C10—H10	0.9300
O4—Zn1iii	1.965 (3)	C11—C12	1.380 (12)
C3—C2	1.377 (7)	C11—H11	0.9300
C3—C4	1.412 (6)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.530 (9)
N2—C10	1.324 (9)	C13—H13A	0.9700
N2—C11	1.355 (10)	C13—H13B	0.9700
N3—C10	1.339 (8)	C14—C15	1.515 (9)
N3—C13	1.418 (9)	C14—H14A	0.9700
N3—C12	1.420 (11)	C14—H14B	0.9700
N4—C17	1.291 (11)	C15—C16	1.533 (11)
N4—C18	1.337 (9)	C15—H15A	0.9700
N4—Zn1iv	2.032 (6)	C15—H15B	0.9700
N5—C19	1.308 (12)	C16—H16A	0.9700
N5—C17	1.340 (9)	C16—H16B	0.9700
N5—C16	1.480 (9)	C17—H17	0.9300
C2—C1	1.403 (6)	C18—C19	1.303 (10)
C2—C6	1.509 (7)	C18—H18	0.9300
C1—N1	1.362 (6)	C19—H19	0.9300
C1—C8	1.484 (7)	O1W—H1B	0.870 (10)
N1—C5	1.368 (7)	O1W—H1A	0.871 (10)
C5—C4	1.388 (7)	O3W—O3W'	1.73 (6)
C5—C9	1.489 (8)	O2W'—O2W	1.21 (3)
O1—Zn1—O4i	110.09 (16)	C5—C9—H9B	109.5
O1—Zn1—N2	110.4 (2)	H9A—C9—H9B	109.5
O4i—Zn1—N2	98.4 (2)	C5—C9—H9C	109.5
O1—Zn1—N4ii	116.5 (2)	H9A—C9—H9C	109.5
O4i—Zn1—N4ii	105.2 (2)	H9B—C9—H9C	109.5
N2—Zn1—N4ii	114.5 (3)	N2—C10—N3	114.0 (6)
C6—O1—Zn1	115.4 (4)	N2—C10—H10	123.0
C7—O4—Zn1iii	118.2 (3)	N3—C10—H10	123.0
C2—C3—C4	123.0 (4)	N2—C11—C12	111.8 (7)
C2—C3—H3	118.5	N2—C11—H11	124.1
C4—C3—H3	118.5	C12—C11—H11	124.1
C10—N2—C11	104.4 (6)	C11—C12—N3	104.1 (7)
C10—N2—Zn1	128.6 (5)	C11—C12—H12	128.0
C11—N2—Zn1	126.5 (5)	N3—C12—H12	128.0
C10—N3—C13	129.0 (6)	N3—C13—C14	113.7 (6)
C10—N3—C12	105.7 (5)	N3—C13—H13A	108.8
C13—N3—C12	125.3 (6)	C14—C13—H13A	108.8
C17—N4—C18	107.0 (7)	N3—C13—H13B	108.8
C17—N4—Zn1iv	121.5 (5)	C14—C13—H13B	108.8
C18—N4—Zn1iv	131.5 (5)	H13A—C13—H13B	107.7
C19—N5—C17	106.3 (6)	C15—C14—C13	114.0 (5)
C19—N5—C16	128.5 (6)	C15—C14—H14A	108.8
C17—N5—C16	125.2 (7)	C13—C14—H14A	108.8
C3—C2—C1	118.4 (4)	C15—C14—H14B	108.8
C3—C2—C6	117.7 (4)	C13—C14—H14B	108.8
C1—C2—C6	123.6 (4)	H14A—C14—H14B	107.7
N1—C1—C2	117.3 (4)	C14—C15—C16	112.2 (5)
N1—C1—C8	115.7 (4)	C14—C15—H15A	109.2
C2—C1—C8	126.9 (4)	C16—C15—H15A	109.2
C1—N1—C5	125.7 (4)	C14—C15—H15B	109.2
N1—C5—C4	117.8 (4)	C16—C15—H15B	109.2
N1—C5—C9	115.8 (5)	H15A—C15—H15B	107.9
C4—C5—C9	126.4 (5)	N5—C16—C15	112.6 (6)
C5—C4—C3	117.6 (4)	N5—C16—H16A	109.1
C5—C4—C7	122.8 (5)	C15—C16—H16A	109.1
C3—C4—C7	119.4 (4)	N5—C16—H16B	109.1
O2—C6—O1	122.9 (5)	C15—C16—H16B	109.1
O2—C6—C2	119.7 (4)	H16A—C16—H16B	107.8
O1—C6—C2	117.4 (5)	N4—C17—N5	109.5 (7)
O3—C7—O4	126.0 (5)	N4—C17—H17	125.3
O3—C7—C4	120.2 (5)	N5—C17—H17	125.3
O4—C7—C4	113.7 (4)	C19—C18—N4	108.0 (8)
C1—C8—H8A	109.5	C19—C18—H18	126.0
C1—C8—H8B	109.5	N4—C18—H18	126.0
H8A—C8—H8B	109.5	C18—C19—N5	109.2 (7)
C1—C8—H8C	109.5	C18—C19—H19	125.4
H8A—C8—H8C	109.5	N5—C19—H19	125.4
H8B—C8—H8C	109.5	H1B—O1W—H1A	105 (4)
C5—C9—H9A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1B···O2v	0.87 (4)	1.99 (4)	2.820 (9)	160 (4)
O1W—H1A···N1	0.87 (3)	1.95 (3)	2.736 (10)	149 (5)

Table 1

Selected bond lengths (Å)

Zn1—O1	1.954 (4)
Zn1—O4i	1.965 (3)
Zn1—N2	1.994 (6)
Zn1—N4ii	2.032 (6)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1B⋯O2iii	0.87 (4)	1.99 (4)	2.820 (9)	160 (4)
O1W—H1A⋯N1	0.87 (3)	1.95 (3)	2.736 (10)	149 (5)

Symmetry code: (iii) .