catena-Poly[[bis-(5-chloro-2-nitro-benzoato)copper(II)]-bis-(μ-5-chloro-2-nitro-benzoato)].

In the title compound, [Cu(2)(C(7)H(3)ClNO(4))(4)](n), the coordination geometry around each Cu(II) ion is distorted square-pyramidal. The CuO(5) coordination is formed by five O atoms from the carboxyl-ate groups of five 5-chloro-2-nitro-benzoate ligands. This coordination leads to the formation of centrosymmetric binuclear units which are edge-shared, forming a linear chain along the a axis, with the Cu(II) ions alternately separated by 2.5891 (4) and 3.1763 (4) Å. The chains are inter-connected into a three-dimensional network by C-H⋯O inter-actions.

Related literature

For general background, see: Balaraman et al. (2006 ▶); Tomoya et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Kabbani et al. (2004 ▶); Stachová et al. (2004 ▶).

Experimental

Crystal data

[Cu2(C7H3ClNO4)4]

M = 929.30

Triclinic,

a = 5.0353 (1) Å

b = 11.8001 (3) Å

c = 13.8595 (3) Å

α = 84.539 (2)°

β = 85.553 (1)°

γ = 85.610 (2)°

V = 815.30 (3) Å3

Z = 1

Mo Kα radiation

μ = 1.72 mm−1

T = 100.0 (1) K

0.47 × 0.21 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.498, T max = 0.875

11613 measured reflections

4656 independent reflections

3994 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.116

S = 1.10

4656 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −1.04 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001895/ci2748sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001895/ci2748Isup2.hkl

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

[Cu2(C7H3ClNO4)4]	Z = 1
Mr = 929.30	F(000) = 462
Triclinic, P1	Dx = 1.893 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0353 (1) Å	Cell parameters from 4198 reflections
b = 11.8001 (3) Å	θ = 2.4–33.5°
c = 13.8595 (3) Å	µ = 1.72 mm−1
α = 84.539 (2)°	T = 100 K
β = 85.553 (1)°	Plate, blue
γ = 85.610 (2)°	0.47 × 0.21 × 0.08 mm
V = 815.30 (3) Å3

Bruker APEXII CCD area-detector diffractometer	4656 independent reflections
Radiation source: fine-focus sealed tube	3994 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.498, Tmax = 0.875	k = −16→16
11613 measured reflections	l = −19→19

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0656P)2 + 0.3146P] where P = (Fo2 + 2Fc2)/3
4656 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −1.04 e Å−3

Experimental. The data was collected with the Oxford Cryosystem Cobra low-temperature attachment

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
Cu1	0.21339 (5)	0.05196 (2)	0.471444 (19)	0.01008 (9)
Cl1	0.39928 (16)	0.36470 (6)	0.09685 (5)	0.02730 (16)
Cl2	−0.29870 (15)	−0.38843 (6)	0.13820 (5)	0.02494 (16)
O1	0.6289 (3)	0.09053 (14)	0.45747 (12)	0.0112 (3)
O2	1.0009 (3)	0.17993 (14)	0.40983 (12)	0.0130 (3)
O3	0.6319 (4)	0.29482 (16)	0.56079 (13)	0.0190 (4)
O4	0.2829 (4)	0.41394 (17)	0.56834 (15)	0.0242 (4)
O5	0.2124 (3)	−0.02541 (15)	0.35393 (12)	0.0138 (3)
O6	−0.1564 (3)	−0.11767 (15)	0.40442 (12)	0.0141 (3)
O7	0.1420 (4)	0.10970 (17)	0.17610 (15)	0.0247 (4)
O8	0.5268 (4)	0.0237 (2)	0.13998 (16)	0.0283 (5)
N1	0.4497 (4)	0.35283 (18)	0.52330 (16)	0.0162 (4)
N2	0.2865 (4)	0.02437 (19)	0.16027 (15)	0.0172 (4)
C1	0.4307 (5)	0.3520 (2)	0.41832 (17)	0.0138 (4)
C2	0.2609 (5)	0.4338 (2)	0.3721 (2)	0.0191 (5)
H2A	0.1571	0.4864	0.4073	0.023*
C3	0.2481 (5)	0.4361 (2)	0.2728 (2)	0.0215 (5)
H3A	0.1339	0.4899	0.2403	0.026*
C4	0.4063 (5)	0.3577 (2)	0.22185 (19)	0.0191 (5)
C5	0.5750 (5)	0.2744 (2)	0.26839 (18)	0.0150 (4)
H5A	0.6780	0.2219	0.2329	0.018*
C6	0.5877 (4)	0.2705 (2)	0.36849 (18)	0.0128 (4)
C7	0.7537 (4)	0.1749 (2)	0.41697 (16)	0.0116 (4)
C8	0.0272 (4)	−0.0881 (2)	0.34205 (17)	0.0125 (4)
C9	0.0247 (5)	−0.1317 (2)	0.24379 (17)	0.0131 (4)
C10	0.1569 (5)	−0.0832 (2)	0.16019 (18)	0.0156 (5)
C11	0.1618 (5)	−0.1279 (2)	0.07137 (19)	0.0209 (5)
H11A	0.2577	−0.0948	0.0173	0.025*
C12	0.0212 (5)	−0.2231 (2)	0.06434 (19)	0.0217 (5)
H12A	0.0200	−0.2545	0.0053	0.026*
C13	−0.1169 (5)	−0.2706 (2)	0.14635 (19)	0.0187 (5)
C14	−0.1152 (5)	−0.2281 (2)	0.23593 (18)	0.0168 (5)
H14A	−0.2060	−0.2632	0.2903	0.020*

	U11	U22	U33	U12	U13	U23
Cu1	0.00866 (14)	0.01013 (15)	0.01168 (15)	−0.00058 (9)	−0.00121 (9)	−0.00174 (10)
Cl1	0.0418 (4)	0.0235 (3)	0.0178 (3)	−0.0067 (3)	−0.0126 (3)	0.0037 (2)
Cl2	0.0375 (4)	0.0189 (3)	0.0210 (3)	−0.0106 (3)	−0.0089 (3)	−0.0029 (2)
O1	0.0094 (7)	0.0094 (8)	0.0142 (7)	0.0000 (6)	−0.0016 (6)	0.0014 (6)
O2	0.0087 (7)	0.0118 (8)	0.0181 (8)	0.0005 (6)	−0.0013 (6)	0.0012 (6)
O3	0.0224 (9)	0.0174 (9)	0.0175 (9)	0.0029 (7)	−0.0051 (7)	−0.0030 (7)
O4	0.0250 (10)	0.0228 (10)	0.0237 (10)	0.0053 (8)	0.0051 (8)	−0.0068 (8)
O5	0.0148 (8)	0.0154 (8)	0.0120 (7)	−0.0021 (6)	−0.0019 (6)	−0.0032 (6)
O6	0.0135 (7)	0.0151 (8)	0.0144 (8)	−0.0012 (6)	−0.0007 (6)	−0.0049 (6)
O7	0.0288 (10)	0.0179 (10)	0.0275 (10)	−0.0044 (8)	−0.0037 (8)	−0.0001 (8)
O8	0.0184 (9)	0.0366 (12)	0.0305 (11)	−0.0099 (8)	0.0025 (8)	−0.0026 (9)
N1	0.0169 (9)	0.0138 (10)	0.0181 (10)	−0.0024 (7)	0.0002 (8)	−0.0021 (8)
N2	0.0204 (10)	0.0178 (11)	0.0137 (9)	−0.0049 (8)	−0.0012 (8)	−0.0004 (8)
C1	0.0140 (10)	0.0113 (11)	0.0164 (11)	−0.0027 (8)	−0.0004 (8)	−0.0023 (8)
C2	0.0167 (11)	0.0139 (12)	0.0264 (13)	−0.0007 (9)	−0.0003 (9)	−0.0013 (10)
C3	0.0182 (11)	0.0162 (12)	0.0299 (14)	0.0012 (9)	−0.0099 (10)	0.0040 (10)
C4	0.0229 (12)	0.0191 (13)	0.0164 (11)	−0.0073 (10)	−0.0057 (9)	0.0014 (9)
C5	0.0178 (11)	0.0127 (11)	0.0149 (11)	−0.0032 (8)	−0.0024 (8)	−0.0005 (8)
C6	0.0100 (9)	0.0100 (10)	0.0185 (11)	−0.0021 (8)	−0.0015 (8)	0.0002 (8)
C7	0.0136 (10)	0.0113 (10)	0.0104 (9)	−0.0026 (8)	−0.0001 (8)	−0.0033 (8)
C8	0.0126 (10)	0.0114 (11)	0.0138 (10)	0.0001 (8)	−0.0018 (8)	−0.0022 (8)
C9	0.0132 (10)	0.0134 (11)	0.0132 (10)	−0.0001 (8)	−0.0025 (8)	−0.0032 (8)
C10	0.0149 (10)	0.0146 (11)	0.0176 (11)	−0.0027 (8)	−0.0012 (8)	−0.0010 (9)
C11	0.0232 (12)	0.0250 (14)	0.0145 (11)	−0.0040 (10)	−0.0002 (9)	−0.0012 (10)
C12	0.0273 (13)	0.0242 (14)	0.0151 (11)	−0.0021 (10)	−0.0033 (10)	−0.0078 (10)
C13	0.0222 (12)	0.0157 (12)	0.0197 (12)	−0.0031 (9)	−0.0063 (9)	−0.0033 (9)
C14	0.0196 (11)	0.0153 (12)	0.0155 (11)	−0.0029 (9)	−0.0016 (9)	0.0000 (9)

Cu1—O5	1.942 (2)	C1—C2	1.384 (4)
Cu1—O6i	1.946 (2)	C1—C6	1.397 (3)
Cu1—O2ii	1.950 (2)	C2—C3	1.381 (4)
Cu1—O1iii	2.008 (2)	C2—H2A	0.93
Cu1—O1	2.165 (2)	C3—C4	1.383 (4)
Cu1—Cu1i	2.5891 (5)	C3—H3A	0.93
Cl1—C4	1.729 (3)	C4—C5	1.393 (4)
Cl2—C13	1.739 (3)	C5—C6	1.390 (3)
O1—C7	1.279 (3)	C5—H5A	0.93
O1—Cu1iii	2.0075 (17)	C6—C7	1.490 (3)
O2—C7	1.246 (3)	C8—C9	1.502 (3)
O2—Cu1iv	1.9501 (17)	C9—C10	1.388 (3)
O3—N1	1.221 (3)	C9—C14	1.400 (3)
O4—N1	1.236 (3)	C10—C11	1.382 (3)
O5—C8	1.263 (3)	C11—C12	1.388 (4)
O6—C8	1.262 (3)	C11—H11A	0.93
O6—Cu1i	1.9459 (16)	C12—C13	1.380 (4)
O7—N2	1.223 (3)	C12—H12A	0.93
O8—N2	1.220 (3)	C13—C14	1.383 (3)
N1—C1	1.466 (3)	C14—H14A	0.93
N2—C10	1.472 (3)
O5—Cu1—O6i	170.11 (7)	C4—C3—H3A	120.3
O5—Cu1—O2ii	88.98 (7)	C3—C4—C5	121.7 (2)
O6i—Cu1—O2ii	90.41 (7)	C3—C4—Cl1	119.2 (2)
O5—Cu1—O1iii	90.80 (7)	C5—C4—Cl1	119.1 (2)
O6i—Cu1—O1iii	88.11 (7)	C6—C5—C4	119.3 (2)
O2ii—Cu1—O1iii	170.10 (6)	C6—C5—H5A	120.3
O5—Cu1—O1	97.86 (7)	C4—C5—H5A	120.3
O6i—Cu1—O1	91.67 (6)	C5—C6—C1	118.1 (2)
O2ii—Cu1—O1	108.91 (7)	C5—C6—C7	117.9 (2)
O1iii—Cu1—O1	80.92 (7)	C1—C6—C7	123.9 (2)
O5—Cu1—Cu1i	85.61 (5)	O2—C7—O1	125.4 (2)
O6i—Cu1—Cu1i	84.53 (5)	O2—C7—C6	118.2 (2)
O2ii—Cu1—Cu1i	90.98 (5)	O1—C7—C6	116.31 (19)
O1iii—Cu1—Cu1i	79.14 (5)	O6—C8—O5	126.5 (2)
O1—Cu1—Cu1i	159.80 (5)	O6—C8—C9	116.6 (2)
C7—O1—Cu1iii	127.17 (15)	O5—C8—C9	116.8 (2)
C7—O1—Cu1	133.75 (15)	C10—C9—C14	117.8 (2)
Cu1iii—O1—Cu1	99.07 (7)	C10—C9—C8	123.8 (2)
C7—O2—Cu1iv	117.23 (15)	C14—C9—C8	118.4 (2)
C8—O5—Cu1	120.91 (15)	C11—C10—C9	122.9 (2)
C8—O6—Cu1i	121.94 (15)	C11—C10—N2	115.9 (2)
O3—N1—O4	123.8 (2)	C9—C10—N2	121.1 (2)
O3—N1—C1	118.2 (2)	C10—C11—C12	118.8 (2)
O4—N1—C1	118.0 (2)	C10—C11—H11A	120.6
O8—N2—O7	124.6 (2)	C12—C11—H11A	120.6
O8—N2—C10	118.2 (2)	C13—C12—C11	119.0 (2)
O7—N2—C10	117.1 (2)	C13—C12—H12A	120.5
C2—C1—C6	122.5 (2)	C11—C12—H12A	120.5
C2—C1—N1	118.5 (2)	C12—C13—C14	122.2 (2)
C6—C1—N1	119.0 (2)	C12—C13—Cl2	119.5 (2)
C3—C2—C1	118.9 (2)	C14—C13—Cl2	118.3 (2)
C3—C2—H2A	120.6	C13—C14—C9	119.3 (2)
C1—C2—H2A	120.6	C13—C14—H14A	120.4
C2—C3—C4	119.5 (3)	C9—C14—H14A	120.4
C2—C3—H3A	120.3
O5—Cu1—O1—C7	89.7 (2)	Cu1iii—O1—C7—O2	4.5 (3)
O6i—Cu1—O1—C7	−92.9 (2)	Cu1—O1—C7—O2	−174.59 (15)
O2ii—Cu1—O1—C7	−1.9 (2)	Cu1iii—O1—C7—C6	179.81 (14)
O1iii—Cu1—O1—C7	179.3 (2)	Cu1—O1—C7—C6	0.7 (3)
Cu1i—Cu1—O1—C7	−171.52 (14)	C5—C6—C7—O2	76.9 (3)
O5—Cu1—O1—Cu1iii	−89.55 (8)	C1—C6—C7—O2	−107.4 (3)
O6i—Cu1—O1—Cu1iii	87.82 (8)	C5—C6—C7—O1	−98.7 (2)
O2ii—Cu1—O1—Cu1iii	178.83 (6)	C1—C6—C7—O1	77.0 (3)
O1iii—Cu1—O1—Cu1iii	0.000 (2)	Cu1i—O6—C8—O5	8.8 (3)
Cu1i—Cu1—O1—Cu1iii	9.18 (17)	Cu1i—O6—C8—C9	−171.10 (15)
O2ii—Cu1—O5—C8	−88.27 (18)	Cu1—O5—C8—O6	−7.7 (3)
O1iii—Cu1—O5—C8	81.83 (18)	Cu1—O5—C8—C9	172.23 (15)
O1—Cu1—O5—C8	162.78 (18)	O6—C8—C9—C10	160.5 (2)
Cu1i—Cu1—O5—C8	2.79 (17)	O5—C8—C9—C10	−19.5 (4)
O3—N1—C1—C2	−167.1 (2)	O6—C8—C9—C14	−20.7 (3)
O4—N1—C1—C2	11.5 (3)	O5—C8—C9—C14	159.4 (2)
O3—N1—C1—C6	11.7 (3)	C14—C9—C10—C11	−1.9 (4)
O4—N1—C1—C6	−169.6 (2)	C8—C9—C10—C11	177.0 (2)
C6—C1—C2—C3	−0.8 (4)	C14—C9—C10—N2	174.1 (2)
N1—C1—C2—C3	177.9 (2)	C8—C9—C10—N2	−7.1 (4)
C1—C2—C3—C4	−0.6 (4)	O8—N2—C10—C11	−64.3 (3)
C2—C3—C4—C5	1.5 (4)	O7—N2—C10—C11	112.1 (3)
C2—C3—C4—Cl1	−177.4 (2)	O8—N2—C10—C9	119.4 (3)
C3—C4—C5—C6	−0.8 (4)	O7—N2—C10—C9	−64.1 (3)
Cl1—C4—C5—C6	178.02 (18)	C9—C10—C11—C12	2.3 (4)
C4—C5—C6—C1	−0.6 (3)	N2—C10—C11—C12	−173.9 (2)
C4—C5—C6—C7	175.3 (2)	C10—C11—C12—C13	−0.6 (4)
C2—C1—C6—C5	1.5 (3)	C11—C12—C13—C14	−1.5 (4)
N1—C1—C6—C5	−177.3 (2)	C11—C12—C13—Cl2	178.9 (2)
C2—C1—C6—C7	−174.2 (2)	C12—C13—C14—C9	1.8 (4)
N1—C1—C6—C7	7.0 (3)	Cl2—C13—C14—C9	−178.53 (19)
Cu1iv—O2—C7—O1	−3.4 (3)	C10—C9—C14—C13	−0.2 (4)
Cu1iv—O2—C7—C6	−178.60 (15)	C8—C9—C14—C13	−179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4v	0.93	2.44	3.254 (3)	146
C11—H11A···O8vi	0.93	2.46	3.384 (3)	172
C14—H14A···O4i	0.93	2.54	3.417 (3)	156

Table 1

Selected bond lengths (Å)

Cu1—O5	1.942 (2)
Cu1—O6i	1.946 (2)
Cu1—O2ii	1.950 (2)
Cu1—O1iii	2.008 (2)
Cu1—O1	2.165 (2)

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

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4iv	0.93	2.44	3.254 (3)	146
C11—H11A⋯O8v	0.93	2.46	3.384 (3)	172
C14—H14A⋯O4i	0.93	2.54	3.417 (3)	156

Symmetry codes: (i) ; (iv) ; (v) .