Poly[(μ(2)-4,4'-bipyridine-κN:N')bis-(μ(4)-cyclo-hexane-1,3-dicarboxyl-ato-κO:O':O'':O''')dizinc(II)].

The cyclo-hexane-1,3-dicarboxyl-ate dianion in the title three-dimensional coordination polymer, [Zn(2)(C(8)H(10)O(4))(2)(C(10)H(8)N(2))](n), has one carboxyl-ate group in an equatorial position and the other in an axial position of the cyclo-hexane ring, which adopts a chair conformation. The carboxyl-ate groups function as bridges to two adjacent Zn(II) atoms, generating a layer motif. Adjacent layers are linked through the 4,4'-bipyridine N-heterocycle, forming a three-dimensional network; the geometry of Zn(II) is square-pyramidal with the N atom of the N-heterocycle occupying the apical position. The N-heterocycle lies about a center of inversion and is disordered in a 1:1 ratio with respect to the C atoms bearing H atoms.

Related literature

For the zinc cyclo­hexane-1,3-dicarboxyl­ate adduct of 1,10-phenanthroline, see: Bailey et al. (2008 ▶).

Experimental

Crystal data

[Zn2(C8H10O4)2(C10H8N2)]

M = 313.64

Monoclinic,

a = 22.251 (2) Å

b = 13.436 (1) Å

c = 8.552 (1) Å

β = 104.446 (5)°

V = 2475.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.99 mm−1

T = 100 K

0.12 × 0.02 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.557, T max = 1.000

8536 measured reflections

2175 independent reflections

1407 reflections with I > 2σ(I)

R int = 0.116

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.123

S = 0.99

2175 reflections

184 parameters

36 restraints

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.65 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHELL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035168/tk2535sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035168/tk2535Isup2.hkl

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

[Zn2(C8H10O4)2(C10H8N2)]	F(000) = 1288
Mr = 313.64	Dx = 1.683 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 543 reflections
a = 22.251 (2) Å	θ = 2.8–21.0°
b = 13.436 (1) Å	µ = 1.99 mm−1
c = 8.552 (1) Å	T = 100 K
β = 104.446 (5)°	Prism, colorless
V = 2475.8 (3) Å3	0.12 × 0.02 × 0.02 mm
Z = 8

Bruker SMART APEX diffractometer	2175 independent reflections
Radiation source: fine-focus sealed tube	1407 reflections with I > 2σ(I)
graphite	Rint = 0.116
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→25
Tmin = 0.557, Tmax = 1.000	k = −15→15
8536 measured reflections	l = −10→10

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3
2175 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.77 e Å−3
36 restraints	Δρmin = −0.65 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.30423 (3)	0.80190 (5)	0.58500 (8)	0.0148 (2)
O1	0.33841 (19)	0.7868 (3)	0.3855 (5)	0.0226 (10)
O2	0.25270 (18)	0.7072 (3)	0.2612 (4)	0.0220 (10)
O3	0.24532 (18)	0.4228 (3)	0.0174 (4)	0.0192 (9)
O4	0.33149 (18)	0.3418 (3)	0.1412 (5)	0.0196 (10)
N1	0.3745 (2)	0.8727 (3)	0.7432 (5)	0.0157 (11)
C1	0.3081 (3)	0.7349 (4)	0.2723 (7)	0.0182 (14)
C2	0.3373 (3)	0.7034 (4)	0.1370 (7)	0.0190 (13)
H2	0.3281	0.7563	0.0521	0.023*
C3	0.4082 (3)	0.6950 (4)	0.1978 (7)	0.0207 (13)
H3A	0.4265	0.6834	0.1052	0.025*
H3B	0.4252	0.7581	0.2503	0.025*
C4	0.4259 (3)	0.6096 (4)	0.3182 (7)	0.0218 (14)
H4A	0.4716	0.6040	0.3530	0.026*
H4B	0.4104	0.6239	0.4148	0.026*
C5	0.3985 (3)	0.5113 (4)	0.2433 (7)	0.0232 (15)
H5A	0.4182	0.4929	0.1556	0.028*
H5B	0.4080	0.4584	0.3263	0.028*
C6	0.3287 (3)	0.5179 (4)	0.1755 (7)	0.0183 (14)
H6	0.3108	0.5325	0.2693	0.022*
C7	0.3106 (3)	0.6056 (4)	0.0586 (7)	0.0194 (14)
H7A	0.3261	0.5935	−0.0386	0.023*
H7B	0.2648	0.6107	0.0240	0.023*
C8	0.3000 (3)	0.4193 (4)	0.1038 (7)	0.0180 (14)
C9	0.4299 (6)	0.8277 (15)	0.8020 (17)	0.015 (3)	0.50
H9	0.4346	0.7607	0.7715	0.019*	0.50
C10	0.4800 (11)	0.8744 (6)	0.9043 (19)	0.022 (3)	0.50
H10	0.5181	0.8400	0.9432	0.027*	0.50
C9'	0.4219 (6)	0.8212 (16)	0.8385 (15)	0.015 (3)	0.50
H9'	0.4213	0.7506	0.8346	0.019*	0.50
C10'	0.4713 (10)	0.8691 (6)	0.942 (2)	0.022 (3)	0.50
H10'	0.5040	0.8311	1.0076	0.027*	0.50
C11	0.4734 (2)	0.9726 (4)	0.9490 (6)	0.0155 (13)
C12	0.4164 (6)	1.0188 (15)	0.8894 (17)	0.016 (3)	0.50
H12	0.4102	1.0856	0.9184	0.019*	0.50
C13	0.3687 (11)	0.9669 (6)	0.7878 (19)	0.014 (2)	0.50
H13	0.3301	0.9996	0.7477	0.017*	0.50
C12'	0.4238 (6)	1.0236 (16)	0.8504 (16)	0.016 (3)	0.50
H12'	0.4230	1.0943	0.8524	0.019*	0.50
C13'	0.3758 (10)	0.9721 (6)	0.750 (2)	0.014 (2)	0.50
H13'	0.3425	1.0085	0.6828	0.017*	0.50

	U11	U22	U33	U12	U13	U23
Zn1	0.0119 (4)	0.0150 (4)	0.0150 (3)	−0.0020 (3)	−0.0011 (2)	−0.0008 (3)
O1	0.027 (2)	0.021 (2)	0.021 (2)	−0.0065 (19)	0.0087 (19)	−0.0056 (18)
O2	0.019 (2)	0.030 (3)	0.017 (2)	−0.002 (2)	0.0051 (18)	−0.0029 (18)
O3	0.011 (2)	0.018 (2)	0.023 (2)	0.0018 (18)	−0.0065 (19)	0.0021 (18)
O4	0.021 (3)	0.013 (2)	0.021 (2)	0.0026 (18)	−0.0026 (19)	−0.0014 (17)
N1	0.016 (3)	0.018 (3)	0.013 (2)	0.001 (2)	0.003 (2)	−0.003 (2)
C1	0.024 (4)	0.008 (3)	0.022 (3)	0.000 (2)	0.005 (3)	0.002 (2)
C2	0.023 (3)	0.017 (3)	0.016 (3)	0.000 (3)	0.004 (3)	−0.002 (3)
C3	0.017 (3)	0.020 (3)	0.025 (3)	−0.004 (3)	0.006 (3)	−0.005 (3)
C4	0.017 (4)	0.027 (4)	0.020 (3)	0.003 (3)	0.004 (3)	−0.005 (3)
C5	0.020 (4)	0.021 (3)	0.027 (4)	0.000 (3)	0.003 (3)	0.000 (3)
C6	0.015 (4)	0.017 (3)	0.021 (3)	−0.002 (3)	0.000 (3)	0.002 (3)
C7	0.024 (4)	0.019 (3)	0.014 (3)	−0.001 (3)	0.003 (3)	−0.003 (2)
C8	0.026 (4)	0.015 (3)	0.013 (3)	−0.001 (3)	0.005 (3)	0.001 (3)
C9	0.025 (5)	0.013 (4)	0.011 (6)	−0.001 (4)	0.008 (4)	0.005 (4)
C10	0.018 (6)	0.022 (4)	0.022 (7)	0.000 (3)	−0.004 (4)	0.007 (3)
C9'	0.025 (5)	0.013 (4)	0.011 (6)	−0.001 (4)	0.008 (4)	0.005 (4)
C10'	0.018 (6)	0.022 (4)	0.022 (7)	0.000 (3)	−0.004 (4)	0.007 (3)
C11	0.010 (3)	0.021 (3)	0.013 (3)	−0.002 (3)	−0.001 (3)	−0.001 (2)
C12	0.015 (4)	0.017 (3)	0.017 (6)	−0.002 (3)	0.009 (4)	−0.006 (4)
C13	0.008 (5)	0.018 (3)	0.015 (7)	0.001 (3)	0.000 (4)	−0.002 (3)
C12'	0.015 (4)	0.017 (3)	0.017 (6)	−0.002 (3)	0.009 (4)	−0.006 (4)
C13'	0.008 (5)	0.018 (3)	0.015 (7)	0.001 (3)	0.000 (4)	−0.002 (3)

Zn1—O1	2.044 (4)	C4—H4B	0.9900
Zn1—O2i	2.045 (4)	C5—C6	1.519 (8)
Zn1—O3ii	2.034 (4)	C5—H5A	0.9900
Zn1—O4iii	2.044 (4)	C5—H5B	0.9900
Zn1—N1	2.031 (5)	C6—C8	1.532 (8)
Zn1—Zn1i	2.8517 (13)	C6—C7	1.533 (7)
O1—C1	1.246 (7)	C6—H6	1.0000
O2—C1	1.267 (7)	C7—H7A	0.9900
O2—Zn1i	2.045 (4)	C7—H7B	0.9900
O3—C8	1.257 (7)	C9—C10	1.384 (10)
O3—Zn1iv	2.034 (4)	C9—H9	0.9500
O4—C8	1.252 (7)	C10—C11	1.392 (10)
O4—Zn1v	2.044 (4)	C10—H10	0.9500
N1—C13'	1.338 (9)	C9'—C10'	1.385 (10)
N1—C13	1.338 (9)	C9'—H9'	0.9500
N1—C9'	1.351 (9)	C10'—C11	1.393 (10)
N1—C9	1.351 (9)	C10'—H10'	0.9500
C1—C2	1.522 (8)	C11—C12'	1.390 (10)
C2—C7	1.526 (7)	C11—C12	1.391 (10)
C2—C3	1.537 (8)	C11—C11vi	1.478 (11)
C2—H2	1.0000	C12—C13	1.380 (10)
C3—C4	1.526 (8)	C12—H12	0.9500
C3—H3A	0.9900	C13—H13	0.9500
C3—H3B	0.9900	C12'—C13'	1.380 (10)
C4—C5	1.526 (8)	C12'—H12'	0.9500
C4—H4A	0.9900	C13'—H13'	0.9500
N1—Zn1—O3ii	99.06 (17)	C6—C5—H5B	109.2
N1—Zn1—O2i	95.55 (16)	C4—C5—H5B	109.2
O3ii—Zn1—O2i	88.19 (16)	H5A—C5—H5B	107.9
N1—Zn1—O1	102.59 (16)	C5—C6—C8	112.8 (5)
O3ii—Zn1—O1	89.70 (15)	C5—C6—C7	111.8 (5)
O2i—Zn1—O1	161.85 (15)	C8—C6—C7	112.9 (5)
N1—Zn1—O4iii	98.71 (17)	C5—C6—H6	106.3
O3ii—Zn1—O4iii	162.21 (15)	C8—C6—H6	106.3
O2i—Zn1—O4iii	89.29 (16)	C7—C6—H6	106.3
O1—Zn1—O4iii	87.23 (15)	C2—C7—C6	111.4 (5)
N1—Zn1—Zn1i	169.00 (12)	C2—C7—H7A	109.3
O3ii—Zn1—Zn1i	82.66 (11)	C6—C7—H7A	109.3
O2i—Zn1—Zn1i	73.59 (11)	C2—C7—H7B	109.3
O1—Zn1—Zn1i	88.25 (12)	C6—C7—H7B	109.3
O4iii—Zn1—Zn1i	79.73 (11)	H7A—C7—H7B	108.0
C1—O1—Zn1	117.5 (4)	O4—C8—O3	125.4 (5)
C1—O2—Zn1i	135.7 (4)	O4—C8—C6	117.8 (5)
C8—O3—Zn1iv	124.3 (4)	O3—C8—C6	116.7 (5)
C8—O4—Zn1v	127.7 (4)	N1—C9—C10	123 (2)
C13'—N1—C9'	118.7 (15)	N1—C9—H9	118.4
C13—N1—C9'	115.4 (14)	C10—C9—H9	118.4
C13'—N1—C9	115.0 (15)	C9—C10—C11	119 (2)
C13—N1—C9	117.4 (15)	C9—C10—H10	120.6
C13'—N1—Zn1	120.0 (11)	C11—C10—H10	120.6
C13—N1—Zn1	121.4 (11)	N1—C9'—C10'	122 (2)
C9'—N1—Zn1	121.2 (11)	N1—C9'—H9'	119.2
C9—N1—Zn1	121.2 (11)	C10'—C9'—H9'	119.2
O1—C1—O2	123.4 (5)	C9'—C10'—C11	120 (2)
O1—C1—C2	119.6 (5)	C9'—C10'—H10'	119.8
O2—C1—C2	116.9 (5)	C11—C10'—H10'	119.8
C7—C2—C1	112.3 (5)	C12'—C11—C10	115.0 (14)
C7—C2—C3	109.8 (5)	C12—C11—C10	118.1 (14)
C1—C2—C3	111.1 (5)	C12'—C11—C10'	116.8 (14)
C7—C2—H2	107.8	C12—C11—C10'	114.3 (14)
C1—C2—H2	107.8	C12'—C11—C11vi	120.7 (12)
C3—C2—H2	107.8	C12—C11—C11vi	121.1 (12)
C4—C3—C2	110.7 (5)	C10—C11—C11vi	120.7 (12)
C4—C3—H3A	109.5	C10'—C11—C11vi	122.5 (11)
C2—C3—H3A	109.5	C13—C12—C11	120 (2)
C4—C3—H3B	109.5	C13—C12—H12	120.2
C2—C3—H3B	109.5	C11—C12—H12	120.2
H3A—C3—H3B	108.1	N1—C13—C12	123 (2)
C5—C4—C3	111.0 (5)	N1—C13—H13	118.5
C5—C4—H4A	109.4	C12—C13—H13	118.5
C3—C4—H4A	109.4	C13'—C12'—C11	120 (2)
C5—C4—H4B	109.4	C13'—C12'—H12'	119.8
C3—C4—H4B	109.4	C11—C12'—H12'	119.8
H4A—C4—H4B	108.0	N1—C13'—C12'	122 (2)
C6—C5—C4	111.9 (5)	N1—C13'—H13'	118.9
C6—C5—H5A	109.2	C12'—C13'—H13'	118.9
C4—C5—H5A	109.2
N1—Zn1—O1—C1	171.8 (4)	C3—C2—C7—C6	56.6 (6)
O3ii—Zn1—O1—C1	−89.0 (4)	C5—C6—C7—C2	−54.5 (6)
O2i—Zn1—O1—C1	−5.7 (7)	C8—C6—C7—C2	177.0 (5)
O4iii—Zn1—O1—C1	73.5 (4)	Zn1v—O4—C8—O3	−3.1 (8)
Zn1i—Zn1—O1—C1	−6.3 (4)	Zn1v—O4—C8—C6	173.7 (3)
O3ii—Zn1—N1—C13'	−0.6 (6)	Zn1iv—O3—C8—O4	−0.9 (8)
O2i—Zn1—N1—C13'	−89.7 (6)	Zn1iv—O3—C8—C6	−177.8 (3)
O1—Zn1—N1—C13'	91.1 (6)	C5—C6—C8—O4	16.7 (7)
O4iii—Zn1—N1—C13'	−179.8 (6)	C7—C6—C8—O4	144.6 (5)
Zn1i—Zn1—N1—C13'	−98.8 (9)	C5—C6—C8—O3	−166.2 (5)
O3ii—Zn1—N1—C13	19.4 (6)	C7—C6—C8—O3	−38.3 (7)
O2i—Zn1—N1—C13	−69.6 (6)	C13'—N1—C9—C10	19.0 (10)
O1—Zn1—N1—C13	111.2 (6)	C13—N1—C9—C10	−0.1 (3)
O4iii—Zn1—N1—C13	−159.8 (6)	Zn1—N1—C9—C10	177.0 (3)
Zn1i—Zn1—N1—C13	−78.8 (10)	N1—C9—C10—C11	−0.2 (3)
O3ii—Zn1—N1—C9'	−177.8 (6)	C13'—N1—C9'—C10'	−0.1 (3)
O2i—Zn1—N1—C9'	93.2 (6)	Zn1—N1—C9'—C10'	177.1 (3)
O1—Zn1—N1—C9'	−86.0 (6)	N1—C9'—C10'—C11	−0.3 (3)
O4iii—Zn1—N1—C9'	3.0 (6)	C9—C10—C11—C12'	−18.2 (11)
Zn1i—Zn1—N1—C9'	84.0 (9)	C9—C10—C11—C12	0.6 (6)
O3ii—Zn1—N1—C9	−157.6 (6)	C9—C10—C11—C10'	82 (6)
O2i—Zn1—N1—C9	113.4 (6)	C9—C10—C11—C11vi	−176.8 (5)
O1—Zn1—N1—C9	−65.9 (6)	C9'—C10'—C11—C12'	0.7 (6)
O4iii—Zn1—N1—C9	23.2 (6)	C9'—C10'—C11—C12	19.4 (10)
Zn1i—Zn1—N1—C9	104.2 (9)	C9'—C10'—C11—C10	−87 (6)
Zn1—O1—C1—O2	13.7 (8)	C9'—C10'—C11—C11vi	−177.0 (6)
Zn1—O1—C1—C2	−167.4 (4)	C10—C11—C12—C13	−0.6 (8)
Zn1i—O2—C1—O1	−16.9 (9)	C10'—C11—C12—C13	−19.4 (12)
Zn1i—O2—C1—C2	164.2 (4)	C11vi—C11—C12—C13	176.7 (7)
O1—C1—C2—C7	152.2 (5)	C13'—N1—C13—C12	−86 (7)
O2—C1—C2—C7	−28.9 (7)	C9'—N1—C13—C12	19.2 (12)
O1—C1—C2—C3	28.7 (7)	C9—N1—C13—C12	0.1 (7)
O2—C1—C2—C3	−152.3 (5)	Zn1—N1—C13—C12	−177.0 (5)
C7—C2—C3—C4	−58.1 (6)	C11—C12—C13—N1	0.3 (9)
C1—C2—C3—C4	66.7 (6)	C10'—C11—C12'—C13'	−0.8 (8)
C2—C3—C4—C5	57.2 (6)	C11vi—C11—C12'—C13'	176.9 (6)
C3—C4—C5—C6	−54.6 (7)	C9'—N1—C13'—C12'	0.0 (7)
C4—C5—C6—C8	−178.4 (5)	Zn1—N1—C13'—C12'	−177.3 (5)
C4—C5—C6—C7	53.2 (6)	C11—C12'—C13'—N1	0.5 (9)
C1—C2—C7—C6	−67.6 (6)