catena-Poly[[(2,2'-bipyridine-κN,N')cadmium]-μ(3)-4-nitro-phthalato-κO:O',O'':O'''].

In the title polymeric compound, [Cd(C(8)H(3)NO(6))(C(10)H(8)N(2))](n), two O atoms from both carboxyl-ate groups of a nitro-phthalate anion coordinate to the Cd(II) cation, forming a seven-membered chelate ring and two carboxyl-ate O atoms from another two nitro-phthalate anions and a 2,2'-bipyridine ligand coordinate to the Cd cation to complete the distorted octa-hedral coordination geometry. The carboxyl-ate groups of the nitro-phthalate anion adopt a syn-anti bridging mode, linking adjacent Cd(II) cations and forming a polymeric chain running along the a axis. Weak intra- and inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of coordination polymers, see: Long & Yaghi (2009 ▶); Kurmoo et al. (2009 ▶); Cheetham et al. (2006 ▶). For related complexes with 4-nitro­phthalate ligands, see: Guo & Guo (2007 ▶); Xu et al. (2009 ▶); He et al. (2010 ▶).

Experimental

Crystal data

[Cd(C8H3NO6)(C10H8N2)]

M = 477.70

Monoclinic,

a = 7.3327 (4) Å

b = 17.3786 (9) Å

c = 13.3859 (7) Å

β = 98.149 (2)°

V = 1688.57 (15) Å3

Z = 4

Mo Kα radiation

μ = 1.34 mm−1

T = 293 K

0.50 × 0.30 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.624, T max = 0.911

19676 measured reflections

3825 independent reflections

3452 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.053

S = 1.03

3825 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (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: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000468/xu5128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000468/xu5128Isup2.hkl

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

[Cd(C8H3NO6)(C10H8N2)]	F(000) = 944
Mr = 477.70	Dx = 1.879 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5075 reflections
a = 7.3327 (4) Å	θ = 2.8–27.6°
b = 17.3786 (9) Å	µ = 1.34 mm−1
c = 13.3859 (7) Å	T = 293 K
β = 98.149 (2)°	Sheet, colorless
V = 1688.57 (15) Å3	0.50 × 0.30 × 0.07 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3825 independent reflections
Radiation source: fine-focus sealed tube	3452 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.624, Tmax = 0.911	k = −21→22
19676 measured reflections	l = −17→17

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.053	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0234P)2 + 1.1148P] where P = (Fo2 + 2Fc2)/3
3825 reflections	(Δ/σ)max = 0.003
253 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. Calcd for C18H11N3O6Cd (Mr = 477.71): C, 45.26; H, 2.32; N, 8.80%. Found: C, 45.34; H, 2.27; N, 8.85%. FT—IR (KBr) 3450 b, 3099 w, 3068 w, 3037 w, 1590 vs, 1551 m, 1513 s, 1495 s, 1439 s, 1422 s,1392 s, 1360 s, 1316 w, 1245 m, 1170 m, 1161 m, 1066 w, 1016 s, 905 m, 830 s,771 s, 740 s, 725 w. Thermogravimetric analysis (TGA) shows that compound (I) has a good thermal stability and exhibits no weight loss untill 200 °C.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Cd1	0.285437 (18)	0.580935 (8)	0.487418 (10)	0.02454 (6)
C10	0.7094 (3)	0.77702 (15)	0.51077 (19)	0.0466 (6)
H10	0.8100	0.7885	0.4782	0.056*
O1	−0.0364 (2)	0.41748 (8)	0.63597 (11)	0.0330 (3)
O3	0.5668 (2)	0.41313 (9)	0.65772 (12)	0.0361 (3)
O2	0.17615 (18)	0.46901 (8)	0.55187 (10)	0.0279 (3)
O4	0.5555 (2)	0.53373 (10)	0.60322 (11)	0.0400 (4)
C6	0.3977 (3)	0.50255 (11)	0.74051 (14)	0.0250 (4)
N3	0.1434 (2)	0.65808 (10)	0.60339 (13)	0.0311 (4)
C7	0.1086 (2)	0.45463 (11)	0.63060 (14)	0.0233 (4)
N1	0.0788 (3)	0.57744 (11)	0.96042 (15)	0.0440 (5)
C1	0.2082 (2)	0.48689 (11)	0.72851 (13)	0.0233 (4)
N2	0.4489 (3)	0.69724 (10)	0.52417 (14)	0.0365 (4)
C2	0.1054 (3)	0.50831 (11)	0.80376 (14)	0.0269 (4)
H2	−0.0194	0.4966	0.7979	0.032*
C3	0.1915 (3)	0.54717 (13)	0.88696 (15)	0.0327 (4)
C14	0.2403 (3)	0.71869 (12)	0.64530 (15)	0.0327 (4)
C4	0.3784 (3)	0.56177 (15)	0.90138 (17)	0.0415 (5)
H4	0.4336	0.5869	0.9593	0.050*
C5	0.4821 (3)	0.53847 (14)	0.82832 (16)	0.0373 (5)
H5	0.6086	0.5468	0.8377	0.045*
C16	0.0198 (4)	0.73882 (15)	0.75846 (19)	0.0498 (6)
H16	−0.0202	0.7655	0.8115	0.060*
C17	−0.0804 (3)	0.67790 (14)	0.71452 (18)	0.0434 (5)
H17	−0.1898	0.6630	0.7365	0.052*
C18	−0.0145 (3)	0.63920 (12)	0.63669 (16)	0.0348 (5)
H18	−0.0828	0.5983	0.6062	0.042*
C15	0.1801 (4)	0.76022 (14)	0.72341 (18)	0.0460 (6)
H15	0.2477	0.8021	0.7517	0.055*
O5	−0.0883 (3)	0.57084 (11)	0.94263 (14)	0.0521 (5)
C8	0.5143 (2)	0.48150 (12)	0.66069 (14)	0.0273 (4)
C13	0.4092 (3)	0.74003 (12)	0.60168 (16)	0.0331 (4)
O6	0.1566 (3)	0.60768 (16)	1.03689 (18)	0.0875 (8)
C12	0.5195 (3)	0.80256 (13)	0.63640 (18)	0.0418 (5)
H12	0.4917	0.8317	0.6905	0.050*
C9	0.5963 (3)	0.71551 (14)	0.48055 (19)	0.0444 (6)
H9	0.6238	0.6853	0.4273	0.053*
C11	0.6697 (3)	0.82089 (14)	0.5902 (2)	0.0462 (6)
H11	0.7437	0.8627	0.6125	0.055*

	U11	U22	U33	U12	U13	U23
Cd1	0.02554 (9)	0.02418 (9)	0.02423 (8)	−0.00343 (5)	0.00470 (6)	−0.00128 (5)
C10	0.0415 (14)	0.0370 (13)	0.0619 (16)	−0.0108 (10)	0.0092 (12)	−0.0012 (11)
O1	0.0276 (7)	0.0398 (9)	0.0307 (7)	−0.0110 (6)	0.0014 (6)	0.0029 (6)
O3	0.0315 (8)	0.0406 (9)	0.0370 (8)	0.0067 (6)	0.0079 (6)	−0.0058 (6)
O2	0.0283 (7)	0.0326 (8)	0.0230 (7)	−0.0045 (6)	0.0045 (5)	−0.0015 (5)
O4	0.0322 (8)	0.0532 (10)	0.0360 (8)	−0.0075 (7)	0.0097 (6)	0.0086 (7)
C6	0.0229 (9)	0.0276 (10)	0.0245 (9)	0.0005 (7)	0.0035 (7)	0.0007 (7)
N3	0.0359 (10)	0.0253 (9)	0.0314 (9)	0.0009 (7)	0.0026 (7)	−0.0025 (7)
C7	0.0216 (9)	0.0226 (9)	0.0253 (9)	0.0017 (7)	0.0015 (7)	0.0004 (7)
N1	0.0506 (13)	0.0439 (12)	0.0410 (11)	−0.0024 (9)	0.0183 (10)	−0.0138 (9)
C1	0.0239 (9)	0.0229 (9)	0.0232 (9)	0.0011 (7)	0.0033 (7)	0.0014 (7)
N2	0.0397 (10)	0.0297 (9)	0.0403 (10)	−0.0058 (8)	0.0065 (8)	−0.0051 (8)
C2	0.0232 (9)	0.0292 (10)	0.0290 (10)	0.0019 (8)	0.0065 (8)	0.0019 (8)
C3	0.0374 (11)	0.0334 (11)	0.0292 (10)	0.0018 (9)	0.0112 (9)	−0.0046 (8)
C14	0.0424 (12)	0.0250 (10)	0.0298 (10)	0.0021 (9)	0.0016 (9)	−0.0016 (8)
C4	0.0394 (13)	0.0540 (14)	0.0305 (11)	−0.0083 (11)	0.0029 (9)	−0.0149 (10)
C5	0.0257 (10)	0.0533 (14)	0.0325 (11)	−0.0066 (9)	0.0022 (9)	−0.0087 (10)
C16	0.0688 (17)	0.0414 (14)	0.0428 (13)	0.0051 (12)	0.0198 (12)	−0.0086 (11)
C17	0.0475 (14)	0.0390 (13)	0.0461 (13)	0.0065 (10)	0.0157 (11)	0.0033 (10)
C18	0.0379 (12)	0.0280 (11)	0.0385 (11)	0.0023 (9)	0.0051 (9)	0.0007 (9)
C15	0.0609 (16)	0.0359 (13)	0.0414 (13)	−0.0025 (11)	0.0075 (11)	−0.0114 (10)
O5	0.0425 (10)	0.0660 (12)	0.0510 (10)	0.0134 (8)	0.0179 (8)	−0.0088 (9)
C8	0.0174 (9)	0.0397 (12)	0.0243 (9)	−0.0034 (8)	0.0013 (7)	−0.0032 (8)
C13	0.0388 (12)	0.0249 (10)	0.0337 (10)	0.0007 (9)	−0.0011 (9)	0.0001 (8)
O6	0.0757 (15)	0.121 (2)	0.0728 (15)	−0.0328 (15)	0.0343 (12)	−0.0668 (15)
C12	0.0493 (14)	0.0288 (12)	0.0448 (13)	−0.0029 (10)	−0.0016 (11)	−0.0065 (9)
C9	0.0452 (14)	0.0385 (13)	0.0514 (14)	−0.0088 (10)	0.0130 (11)	−0.0079 (11)
C11	0.0466 (14)	0.0287 (12)	0.0603 (15)	−0.0109 (10)	−0.0030 (12)	−0.0031 (11)

Cd1—O1i	2.2820 (15)	N2—C9	1.337 (3)
Cd1—O2	2.3165 (14)	N2—C13	1.342 (3)
Cd1—O3ii	2.3570 (15)	C2—C3	1.377 (3)
Cd1—O4	2.4753 (16)	C2—H2	0.9300
Cd1—N2	2.3659 (18)	C3—C4	1.380 (3)
Cd1—N3	2.3979 (17)	C14—C15	1.393 (3)
C10—C11	1.372 (4)	C14—C13	1.489 (3)
C10—C9	1.378 (3)	C4—C5	1.382 (3)
C10—H10	0.9300	C4—H4	0.9300
O1—C7	1.255 (2)	C5—H5	0.9300
O3—C8	1.251 (2)	C16—C17	1.373 (4)
O2—C7	1.252 (2)	C16—C15	1.377 (4)
O4—C8	1.254 (2)	C16—H16	0.9300
C6—C5	1.396 (3)	C17—C18	1.384 (3)
C6—C1	1.403 (3)	C17—H17	0.9300
C6—C8	1.505 (3)	C18—H18	0.9300
N3—C18	1.339 (3)	C15—H15	0.9300
N3—C14	1.347 (3)	C13—C12	1.395 (3)
C7—C1	1.515 (3)	C12—C11	1.375 (4)
N1—O6	1.218 (3)	C12—H12	0.9300
N1—O5	1.220 (3)	C9—H9	0.9300
N1—C3	1.469 (3)	C11—H11	0.9300
C1—C2	1.392 (3)
O1i—Cd1—O2	89.78 (5)	C3—C2—H2	120.6
O1i—Cd1—O3ii	79.46 (5)	C1—C2—H2	120.6
O2—Cd1—O3ii	124.57 (5)	C2—C3—C4	122.41 (18)
O1i—Cd1—N2	118.03 (6)	C2—C3—N1	118.68 (19)
O2—Cd1—N2	146.28 (6)	C4—C3—N1	118.84 (19)
O3ii—Cd1—N2	81.69 (6)	N3—C14—C15	120.9 (2)
O1i—Cd1—N3	94.91 (6)	N3—C14—C13	116.74 (18)
O2—Cd1—N3	91.34 (5)	C15—C14—C13	122.3 (2)
O3ii—Cd1—N3	143.29 (6)	C3—C4—C5	118.8 (2)
N2—Cd1—N3	68.99 (6)	C3—C4—H4	120.6
O1i—Cd1—O4	160.78 (5)	C5—C4—H4	120.6
O2—Cd1—O4	77.10 (5)	C4—C5—C6	120.3 (2)
O3ii—Cd1—O4	96.33 (5)	C4—C5—H5	119.8
N2—Cd1—O4	79.41 (6)	C6—C5—H5	119.8
N3—Cd1—O4	99.33 (6)	C17—C16—C15	119.6 (2)
C11—C10—C9	118.3 (2)	C17—C16—H16	120.2
C11—C10—H10	120.9	C15—C16—H16	120.2
C9—C10—H10	120.9	C16—C17—C18	118.3 (2)
C7—O1—Cd1i	123.37 (12)	C16—C17—H17	120.8
C8—O3—Cd1ii	99.45 (12)	C18—C17—H17	120.8
C7—O2—Cd1	132.87 (12)	N3—C18—C17	122.8 (2)
C8—O4—Cd1	112.52 (12)	N3—C18—H18	118.6
C5—C6—C1	119.77 (17)	C17—C18—H18	118.6
C5—C6—C8	118.59 (17)	C16—C15—C14	119.5 (2)
C1—C6—C8	121.64 (17)	C16—C15—H15	120.3
C18—N3—C14	118.85 (18)	C14—C15—H15	120.3
C18—N3—Cd1	123.62 (14)	O3—C8—O4	124.44 (18)
C14—N3—Cd1	117.07 (14)	O3—C8—C6	117.51 (17)
O2—C7—O1	126.20 (17)	O4—C8—C6	118.04 (18)
O2—C7—C1	117.06 (16)	N2—C13—C12	120.7 (2)
O1—C7—C1	116.71 (16)	N2—C13—C14	116.68 (19)
O6—N1—O5	122.8 (2)	C12—C13—C14	122.6 (2)
O6—N1—C3	118.4 (2)	C11—C12—C13	119.6 (2)
O5—N1—C3	118.72 (19)	C11—C12—H12	120.2
C2—C1—C6	119.66 (17)	C13—C12—H12	120.2
C2—C1—C7	118.75 (16)	N2—C9—C10	123.1 (2)
C6—C1—C7	121.28 (16)	N2—C9—H9	118.5
C9—N2—C13	118.92 (19)	C10—C9—H9	118.5
C9—N2—Cd1	121.94 (15)	C10—C11—C12	119.4 (2)
C13—N2—Cd1	118.37 (14)	C10—C11—H11	120.3
C3—C2—C1	118.88 (18)	C12—C11—H11	120.3

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O5iii	0.93	2.49	3.349 (3)	154
C9—H9···O3ii	0.93	2.39	3.037 (3)	126
C12—H12···O3iv	0.93	2.56	3.490 (3)	177
C15—H15···O3iv	0.93	2.56	3.493 (3)	176
C18—H18···O2i	0.93	2.43	3.235 (3)	145

Table 1

Selected bond lengths (Å)

Cd1—O1i	2.2820 (15)
Cd1—O2	2.3165 (14)
Cd1—O3ii	2.3570 (15)
Cd1—O4	2.4753 (16)
Cd1—N2	2.3659 (18)
Cd1—N3	2.3979 (17)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O5iii	0.93	2.49	3.349 (3)	154
C9—H9⋯O3ii	0.93	2.39	3.037 (3)	126
C12—H12⋯O3iv	0.93	2.56	3.490 (3)	177
C15—H15⋯O3iv	0.93	2.56	3.493 (3)	176
C18—H18⋯O2i	0.93	2.43	3.235 (3)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .