catena-Poly[[[aqua­copper(II)]-bis­[μ-N,N′-bis­(pyridin-4-yl)isophthalamide]-[aqua­copper(II)]-di-μ-sulfato] dimethyl­formamide disolvate]

Zhang, E.-P.; Wang, L.-P.; Wang, Y.-F.

doi:10.1107/S1600536813003413

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages m150-m151

doi:10.1107/S1600536813003413

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catena-Poly[[[aquacopper(II)]-bis[μ-N,N′-bis(pyridin-4-yl)isophthalamide]-[aquacopper(II)]-di-μ-sulfato] dimethylformamide disolvate]

Er-Peng Zhang,^a ^* Li-Ping Wang ^b and Yu-Fei Wang ^b

^aHenan Center for Disease Control and Prevention, Zhengzhou 450016, People's Republic of China, and ^bCollege of Chemical and Food Engineering, ZhongZhou University, Zhengzhou 450044, People's Republic of China
^*Correspondence e-mail: erpengzhang@163.com

(Received 28 January 2013; accepted 4 February 2013; online 16 February 2013)

In the title coordination polymer, {[Cu(SO₄)(C₁₈H₁₄N₄O₂)(H₂O)]·C₃H₇NO}_n, the Cu^II ion is coordinated by two N atoms of two briding N,N′-bis(pyridin-4-yl)isophthalamide ligands, two O atoms of two bridging SO₄²⁻ anions and a water molecule, giving a distorted CuN₂O₃ square-pyramidal geometry. The whole repeating molecular unit is generated by inversion symmetry. This leads to the formation of a looped-chain one-dimensional coordination polymer propagating along [110]. The dimethylformamide (DMF) molecules are linked to the chains via O—H⋯O hydrogen bonds. The chains are linked via N—H⋯O hydrogen bonds, forming two-dimensional networks parallel to (001). There are also a number of C—H⋯O interactions present and a parallel slipped π–π interaction. The latter involves inversion-related pyridine rings with a centroid–centroid distance of 3.594 (2) Å [normal distance = 3.3338 (13) and slippage = 1.341 Å]. These interactions lead to the formation of a three-dimensional structure.

Related literature

For background to metal complexes with a N,N′-bis-(4-pyridyl)isophthalamide ligand, see: Adarsh et al. (2009 ); Gong et al. (2010 , 2011 ); Kim et al. (2011 ).

Experimental

Crystal data

[Cu(SO₄)(C₁₈H₁₄N₄O₂)(H₂O)]·C₃H₇NO
M_r = 569.06
Triclinic, $[P \overline 1]$
a = 10.389 (2) Å
b = 11.092 (1) Å
c = 12.105 (2) Å
α = 63.47 (3)°
β = 79.75 (2)°
γ = 71.08 (3)°
V = 1179.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.07 mm⁻¹
T = 293 K
0.28 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn 724 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.753, T_max = 0.814
14785 measured reflections
5581 independent reflections
4622 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.124
S = 1.07
5581 reflections
339 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2ⁱ	0.86 (3)	2.03 (3)	2.867 (3)	164 (3)
N4—H4A⋯O3ⁱ	0.87 (3)	2.25 (3)	3.103 (4)	168 (3)
O5—H5A⋯O8ⁱⁱ	0.82 (3)	1.81 (3)	2.626 (4)	179 (4)
O5—H5B⋯O2	0.81 (3)	1.90 (3)	2.684 (3)	164 (4)
C4—H4⋯O8	0.93	2.45	3.325 (4)	157
C18—H18⋯O6ⁱⁱⁱ	0.93	2.55	3.277 (4)	136
C19—H19⋯O4^iv	0.93	2.47	3.286 (4)	146
C20—H20C⋯O3^v	0.96	2.58	3.226 (6)	125
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+2, -z+1; (iii) -x, -y+1, -z+1; (iv) x, y-1, z+1; (v) -x, -y+3, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2006 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813003413/su2555sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003413/su2555Isup2.hkl

checkCIF report

Comment top

The bis-pyridyl-bis-amide ligands have been used to construct various metal-organic frameworks (MOFs), not only due to their conformational flexibility but also due to the multiple hydrogen bonding sites in the ligand backbone (Adarsh et al., 2009; Gong et al., 2010, 2011; Kim et al., 2011). In this work, the bis-pyridyl-bis-amide ligand, N,N'-bis-(4-pyridyl)isophthalamide (bppa), has been used to generate the title coordination polymer whose crystal structure is reported on herein.

The coordination enviroment of the Cu^II center in the title complex is shown in Fig. 1. In the distorted square pyramidal geometry of the Cu^II ion the basal positions are occupied by two pyridyl N atoms of briding bppa ligands (N1 and N2ⁱ), an O atom (O1) of a briding SO₄^2- anion and the O atom (O5) of a coordinated water molecule, while the axial position is occupied by the O atom (O4ⁱⁱ) of a second briding SO₄^2- anion. The Cu^II ions are connected by a pair of bridging SO₄^2- anions, yielding a centrosymmetric Cu₂(SO₄)₂ binuclear unit with a Cu···Cu distance of 4.772( ) Å. The binuclear units are further linked by two bppa ligands to give a looped-chain coordination polymer extending along [1 1 0], as shown in Fig. 2. The distance between two Cu^II ions bridged by the bppa ligands is ca. 13.87 Å.

In the crystal, the chains are linked via N-H···O to form two-dimensional networks extending in the a and b directions. The dimethyl formamide (DMF) molecules are linked to the chains via O-H···O hydrogen bonds (Table 1). There are also a number of C-H···O interactions present and a parallel slipped π-π interaction. The latter involves inversion related N2/C14-C18 pyridine rings with a centroid-to-centroid distance 3.594 (2) Å [normal distance 3.3338 (13) Å, slippage 1.341 Å]. These interactions lead to the formatin of a three-diemnsional structure.

Related literature top

For background to metal complexes with a N,N'-bis-(4-pyridyl)isophthalamide ligand, see: Adarsh et al. (2009); Gong et al. (2010, 2011); Kim et al. (2011).

Experimental top

The ligand N,N'-bis-(4-pyridyl)isophthalamide (0.03 mmol, 10 mg) in DMF (5 ml) was added dropwise to a methanol solution (5 ml) of CuSO₄^.5H₂O; (0.03 mmol, 7.5 mg) in methanol. The resulting solution was allowed to stand at room temperature. After one week good quality blue crystals were obtained.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); 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: publCIF (Westrip, 2010).

Figures top

	Fig. 1. A fragment of the title complex showing the atom labelling. The displacement ellipsoids are drawn at the 30% probability level. H atoms and solvent molecules have been omitted for clarity [symmetry codes: (i) -x, -y+2, -z; (ii) -x+1, -y+3, -z].
	Fig. 2. View of the extended one-dimensional looped-chain structure of the title complex.

catena-Poly[[[aquacopper(II)]-bis[µ-N,N'-bis(pyridin-4-yl)isophthalamide]-[aquacopper(II)]-di-µ-sulfato] dimethylformamide disolvate] top

Crystal data top

[Cu(SO₄)(C₁₈H₁₄N₄O₂)(H₂O)]·C₃H₇NO	Z = 2
M_r = 569.06	F(000) = 586
Triclinic, P1	D_x = 1.602 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.389 (2) Å	Cell parameters from 2540 reflections
b = 11.092 (1) Å	θ = 1.3–25.5°
c = 12.105 (2) Å	µ = 1.07 mm⁻¹
α = 63.47 (3)°	T = 293 K
β = 79.75 (2)°	Prism, blue
γ = 71.08 (3)°	0.28 × 0.24 × 0.20 mm
V = 1179.8 (4) Å³

Data collection top

Rigaku Saturn 724 diffractometer	5581 independent reflections
Radiation source: fine-focus sealed tube	4622 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.9°, θ_min = 2.5°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
T_min = 0.753, T_max = 0.814	l = −15→15
14785 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0562P)² + 0.3078P] where P = (F_o² + 2F_c²)/3
5581 reflections	(Δ/σ)_max = 0.001
339 parameters	Δρ_max = 0.44 e Å⁻³
4 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Cu(SO₄)(C₁₈H₁₄N₄O₂)(H₂O)]·C₃H₇NO	γ = 71.08 (3)°
M_r = 569.06	V = 1179.8 (4) Å³
Triclinic, P1	Z = 2
a = 10.389 (2) Å	Mo Kα radiation
b = 11.092 (1) Å	µ = 1.07 mm⁻¹
c = 12.105 (2) Å	T = 293 K
α = 63.47 (3)°	0.28 × 0.24 × 0.20 mm
β = 79.75 (2)°

Data collection top

Rigaku Saturn 724 diffractometer	5581 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4622 reflections with I > 2σ(I)
T_min = 0.753, T_max = 0.814	R_int = 0.039
14785 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	4 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.44 e Å⁻³
5581 reflections	Δρ_min = −0.48 e Å⁻³
339 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cu1	0.38105 (3)	1.33009 (3)	0.12726 (3)	0.02904 (12)
N1	0.3870 (2)	1.1263 (2)	0.2105 (2)	0.0306 (5)
N2	−0.2404 (2)	0.6278 (2)	−0.0103 (2)	0.0318 (5)
N3	0.3422 (3)	0.7212 (3)	0.3637 (2)	0.0346 (6)
H3A	0.353 (3)	0.686 (3)	0.311 (2)	0.041*
N4	0.0555 (3)	0.5102 (3)	0.2416 (2)	0.0390 (6)
H4A	0.111 (3)	0.562 (3)	0.214 (3)	0.047*
N5	0.0872 (3)	0.9732 (3)	0.7526 (3)	0.0567 (8)
O1	0.3441 (3)	1.5323 (2)	0.0619 (2)	0.0509 (6)
O2	0.4349 (2)	1.5789 (2)	0.20428 (18)	0.0343 (5)
O3	0.2229 (2)	1.7265 (2)	0.1090 (2)	0.0485 (6)
O4	0.4322 (2)	1.7294 (2)	−0.01280 (18)	0.0394 (5)
O5	0.4686 (2)	1.3056 (2)	0.2695 (2)	0.0360 (5)
H5A	0.5446 (18)	1.251 (3)	0.284 (3)	0.054*
H5B	0.474 (4)	1.3836 (18)	0.251 (3)	0.054*
O6	0.3448 (3)	0.6518 (2)	0.57191 (19)	0.0510 (6)
O7	0.0307 (3)	0.2996 (3)	0.3841 (3)	0.0766 (10)
O8	0.2884 (3)	0.8735 (3)	0.6849 (3)	0.0816 (10)
C1	0.4035 (3)	1.0521 (3)	0.1435 (3)	0.0350 (7)
H1	0.4239	1.0942	0.0593	0.042*
C2	0.3919 (3)	0.9193 (3)	0.1921 (3)	0.0350 (7)
H2	0.4033	0.8731	0.1416	0.042*
C3	0.3626 (3)	0.8524 (3)	0.3190 (3)	0.0301 (6)
C4	0.3509 (3)	0.9258 (3)	0.3902 (3)	0.0343 (6)
H4	0.3347	0.8849	0.4753	0.041*
C5	0.3638 (3)	1.0592 (3)	0.3320 (3)	0.0342 (6)
H5	0.3559	1.1069	0.3805	0.041*
C6	0.3258 (3)	0.6324 (3)	0.4860 (3)	0.0332 (6)
C7	0.2840 (3)	0.5079 (3)	0.5039 (3)	0.0308 (6)
C8	0.3220 (3)	0.3856 (3)	0.6112 (3)	0.0357 (7)
H8	0.3719	0.3824	0.6696	0.043*
C9	0.2842 (4)	0.2693 (3)	0.6295 (3)	0.0475 (8)
H9	0.3099	0.1869	0.7003	0.057*
C10	0.2090 (3)	0.2740 (3)	0.5440 (3)	0.0440 (8)
H10	0.1854	0.1944	0.5572	0.053*
C11	0.1680 (3)	0.3970 (3)	0.4378 (3)	0.0341 (6)
C12	0.2061 (3)	0.5133 (3)	0.4189 (3)	0.0313 (6)
H12	0.1793	0.5960	0.3485	0.038*
C13	0.0795 (3)	0.3964 (3)	0.3530 (3)	0.0409 (7)
C14	−0.0426 (3)	0.5437 (3)	0.1590 (3)	0.0340 (6)
C15	−0.0365 (3)	0.6471 (3)	0.0409 (3)	0.0376 (7)
H15	0.0330	0.6907	0.0166	0.045*
C16	−0.1348 (3)	0.6846 (3)	−0.0406 (3)	0.0382 (7)
H16	−0.1282	0.7524	−0.1204	0.046*
C17	−0.2423 (3)	0.5272 (3)	0.1045 (3)	0.0369 (7)
H17	−0.3129	0.4853	0.1275	0.044*
C18	−0.1476 (3)	0.4817 (3)	0.1902 (3)	0.0370 (7)
H18	−0.1538	0.4104	0.2682	0.044*
C19	0.2186 (4)	0.9110 (4)	0.7613 (3)	0.0545 (9)
H19	0.2605	0.8947	0.8304	0.065*
C20	0.0111 (6)	1.0277 (7)	0.8395 (5)	0.117 (2)
H20A	0.0717	1.0157	0.8972	0.175*
H20B	−0.0559	0.9783	0.8832	0.175*
H20C	−0.0336	1.1257	0.7962	0.175*
C21	0.0159 (4)	0.9925 (5)	0.6498 (4)	0.0822 (14)
H21A	0.0778	0.9484	0.6009	0.123*
H21B	−0.0188	1.0909	0.5994	0.123*
H21C	−0.0583	0.9509	0.6814	0.123*
S1	0.35897 (7)	1.64365 (7)	0.09048 (6)	0.02617 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0327 (2)	0.0243 (2)	0.0321 (2)	−0.01067 (15)	−0.00462 (14)	−0.01040 (15)
N1	0.0385 (13)	0.0254 (12)	0.0305 (12)	−0.0126 (10)	−0.0007 (10)	−0.0117 (10)
N2	0.0321 (12)	0.0323 (13)	0.0355 (13)	−0.0133 (10)	−0.0032 (10)	−0.0142 (11)
N3	0.0520 (16)	0.0320 (13)	0.0266 (12)	−0.0217 (12)	0.0028 (11)	−0.0129 (11)
N4	0.0379 (14)	0.0442 (16)	0.0385 (14)	−0.0215 (12)	−0.0046 (11)	−0.0124 (12)
N5	0.0508 (18)	0.0533 (19)	0.0501 (18)	−0.0023 (15)	0.0016 (14)	−0.0175 (15)
O1	0.0801 (18)	0.0271 (11)	0.0528 (14)	−0.0155 (11)	−0.0306 (13)	−0.0125 (10)
O2	0.0414 (12)	0.0321 (11)	0.0329 (11)	−0.0089 (9)	−0.0065 (9)	−0.0155 (9)
O3	0.0326 (12)	0.0469 (14)	0.0551 (14)	0.0003 (10)	0.0030 (10)	−0.0214 (12)
O4	0.0353 (11)	0.0422 (12)	0.0366 (11)	−0.0174 (10)	0.0062 (9)	−0.0111 (10)
O5	0.0409 (12)	0.0268 (11)	0.0405 (12)	−0.0070 (9)	−0.0109 (10)	−0.0126 (10)
O6	0.0858 (19)	0.0503 (14)	0.0287 (11)	−0.0387 (13)	−0.0043 (11)	−0.0123 (10)
O7	0.101 (2)	0.0432 (15)	0.088 (2)	−0.0383 (15)	−0.0528 (18)	0.0010 (14)
O8	0.0632 (18)	0.101 (2)	0.0707 (19)	0.0272 (17)	−0.0212 (15)	−0.0551 (19)
C1	0.0449 (17)	0.0358 (16)	0.0266 (14)	−0.0145 (14)	0.0023 (12)	−0.0142 (13)
C2	0.0505 (18)	0.0317 (15)	0.0296 (14)	−0.0172 (14)	0.0029 (13)	−0.0163 (13)
C3	0.0349 (15)	0.0281 (14)	0.0304 (14)	−0.0122 (12)	−0.0009 (12)	−0.0126 (12)
C4	0.0474 (18)	0.0330 (16)	0.0280 (14)	−0.0186 (14)	0.0027 (12)	−0.0137 (12)
C5	0.0434 (17)	0.0301 (15)	0.0346 (15)	−0.0144 (13)	0.0007 (13)	−0.0164 (13)
C6	0.0380 (16)	0.0323 (15)	0.0303 (14)	−0.0159 (13)	−0.0002 (12)	−0.0103 (12)
C7	0.0335 (15)	0.0302 (15)	0.0295 (14)	−0.0116 (12)	0.0003 (11)	−0.0118 (12)
C8	0.0388 (16)	0.0371 (16)	0.0306 (15)	−0.0140 (13)	−0.0059 (12)	−0.0098 (13)
C9	0.056 (2)	0.0301 (17)	0.0439 (18)	−0.0130 (15)	−0.0169 (16)	0.0015 (14)
C10	0.0509 (19)	0.0300 (16)	0.0484 (19)	−0.0170 (14)	−0.0113 (15)	−0.0068 (14)
C11	0.0344 (15)	0.0295 (15)	0.0387 (16)	−0.0122 (12)	−0.0035 (12)	−0.0114 (13)
C12	0.0357 (15)	0.0287 (15)	0.0284 (14)	−0.0120 (12)	−0.0021 (12)	−0.0085 (12)
C13	0.0429 (18)	0.0350 (17)	0.0471 (18)	−0.0144 (14)	−0.0104 (14)	−0.0135 (15)
C14	0.0342 (15)	0.0360 (16)	0.0387 (16)	−0.0099 (13)	−0.0029 (12)	−0.0209 (14)
C15	0.0337 (15)	0.0378 (17)	0.0423 (17)	−0.0183 (13)	−0.0019 (13)	−0.0118 (14)
C16	0.0402 (17)	0.0351 (17)	0.0388 (16)	−0.0169 (14)	−0.0043 (13)	−0.0095 (13)
C17	0.0352 (16)	0.0431 (18)	0.0370 (16)	−0.0168 (14)	−0.0009 (13)	−0.0168 (14)
C18	0.0359 (16)	0.0463 (18)	0.0323 (15)	−0.0185 (14)	0.0009 (12)	−0.0153 (14)
C19	0.055 (2)	0.053 (2)	0.044 (2)	0.0042 (18)	−0.0135 (17)	−0.0192 (18)
C20	0.101 (4)	0.128 (5)	0.106 (4)	−0.004 (4)	0.036 (4)	−0.069 (4)
C21	0.054 (3)	0.087 (3)	0.094 (4)	−0.019 (2)	−0.022 (2)	−0.021 (3)
S1	0.0283 (3)	0.0230 (3)	0.0297 (3)	−0.0089 (3)	−0.0005 (3)	−0.0122 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.942 (2)	C2—H2	0.9300
Cu1—O5	1.961 (2)	C3—C4	1.395 (4)
Cu1—N1	2.007 (2)	C4—C5	1.367 (4)
Cu1—N2ⁱ	2.015 (2)	C4—H4	0.9300
Cu1—O4ⁱⁱ	2.269 (2)	C5—H5	0.9300
N1—C5	1.337 (3)	C6—C7	1.494 (4)
N1—C1	1.349 (3)	C7—C12	1.389 (4)
N2—C17	1.340 (4)	C7—C8	1.394 (4)
N2—C16	1.354 (4)	C8—C9	1.382 (4)
N2—Cu1ⁱ	2.015 (2)	C8—H8	0.9300
N3—C6	1.381 (3)	C9—C10	1.377 (4)
N3—C3	1.382 (3)	C9—H9	0.9300
N3—H3A	0.86 (3)	C10—C11	1.396 (4)
N4—C13	1.367 (4)	C10—H10	0.9300
N4—C14	1.401 (4)	C11—C12	1.382 (4)
N4—H4A	0.87 (3)	C11—C13	1.497 (4)
N5—C19	1.314 (5)	C12—H12	0.9300
N5—C20	1.435 (5)	C14—C15	1.383 (4)
N5—C21	1.460 (5)	C14—C18	1.384 (4)
O1—S1	1.481 (2)	C15—C16	1.380 (4)
O2—S1	1.473 (2)	C15—H15	0.9300
O3—S1	1.457 (2)	C16—H16	0.9300
O4—S1	1.454 (2)	C17—C18	1.369 (4)
O4—Cu1ⁱⁱ	2.269 (2)	C17—H17	0.9300
O5—H5A	0.82 (3)	C18—H18	0.9300
O5—H5B	0.81 (3)	C19—H19	0.9300
O6—C6	1.211 (3)	C20—H20A	0.9600
O7—C13	1.215 (4)	C20—H20B	0.9600
O8—C19	1.209 (4)	C20—H20C	0.9600
C1—C2	1.359 (4)	C21—H21A	0.9600
C1—H1	0.9300	C21—H21B	0.9600
C2—C3	1.401 (4)	C21—H21C	0.9600

O1—Cu1—O5	90.75 (9)	C7—C8—H8	120.5
O1—Cu1—N1	169.85 (10)	C10—C9—C8	120.8 (3)
O5—Cu1—N1	89.23 (10)	C10—C9—H9	119.6
O1—Cu1—N2ⁱ	85.21 (10)	C8—C9—H9	119.6
O5—Cu1—N2ⁱ	162.72 (10)	C9—C10—C11	120.6 (3)
N1—Cu1—N2ⁱ	91.82 (10)	C9—C10—H10	119.7
O1—Cu1—O4ⁱⁱ	102.68 (10)	C11—C10—H10	119.7
O5—Cu1—O4ⁱⁱ	100.05 (9)	C12—C11—C10	118.8 (3)
N1—Cu1—O4ⁱⁱ	87.31 (9)	C12—C11—C13	123.7 (3)
N2ⁱ—Cu1—O4ⁱⁱ	97.23 (9)	C10—C11—C13	117.5 (3)
C5—N1—C1	116.0 (2)	C11—C12—C7	120.6 (3)
C5—N1—Cu1	123.07 (19)	C11—C12—H12	119.7
C1—N1—Cu1	120.74 (19)	C7—C12—H12	119.7
C17—N2—C16	115.7 (3)	O7—C13—N4	122.5 (3)
C17—N2—Cu1ⁱ	118.66 (19)	O7—C13—C11	120.7 (3)
C16—N2—Cu1ⁱ	125.3 (2)	N4—C13—C11	116.7 (3)
C6—N3—C3	126.9 (2)	C15—C14—C18	118.2 (3)
C6—N3—H3A	116 (2)	C15—C14—N4	118.3 (3)
C3—N3—H3A	116 (2)	C18—C14—N4	123.5 (3)
C13—N4—C14	126.0 (3)	C16—C15—C14	119.1 (3)
C13—N4—H4A	119 (2)	C16—C15—H15	120.4
C14—N4—H4A	115 (2)	C14—C15—H15	120.4
C19—N5—C20	121.9 (4)	N2—C16—C15	123.4 (3)
C19—N5—C21	119.8 (3)	N2—C16—H16	118.3
C20—N5—C21	118.3 (4)	C15—C16—H16	118.3
S1—O1—Cu1	141.81 (14)	N2—C17—C18	124.6 (3)
S1—O4—Cu1ⁱⁱ	131.29 (13)	N2—C17—H17	117.7
Cu1—O5—H5A	116 (3)	C18—C17—H17	117.7
Cu1—O5—H5B	103 (3)	C17—C18—C14	118.8 (3)
H5A—O5—H5B	108 (4)	C17—C18—H18	120.6
N1—C1—C2	123.8 (3)	C14—C18—H18	120.6
N1—C1—H1	118.1	O8—C19—N5	123.9 (4)
C2—C1—H1	118.1	O8—C19—H19	118.0
C1—C2—C3	119.5 (3)	N5—C19—H19	118.0
C1—C2—H2	120.3	N5—C20—H20A	109.5
C3—C2—H2	120.3	N5—C20—H20B	109.5
N3—C3—C4	124.7 (3)	H20A—C20—H20B	109.5
N3—C3—C2	117.8 (2)	N5—C20—H20C	109.5
C4—C3—C2	117.4 (3)	H20A—C20—H20C	109.5
C5—C4—C3	118.4 (3)	H20B—C20—H20C	109.5
C5—C4—H4	120.8	N5—C21—H21A	109.5
C3—C4—H4	120.8	N5—C21—H21B	109.5
N1—C5—C4	124.9 (3)	H21A—C21—H21B	109.5
N1—C5—H5	117.5	N5—C21—H21C	109.5
C4—C5—H5	117.5	H21A—C21—H21C	109.5
O6—C6—N3	123.6 (3)	H21B—C21—H21C	109.5
O6—C6—C7	122.4 (3)	O4—S1—O3	111.13 (14)
N3—C6—C7	114.1 (2)	O4—S1—O2	110.28 (13)
C12—C7—C8	120.2 (3)	O3—S1—O2	109.69 (13)
C12—C7—C6	121.7 (3)	O4—S1—O1	108.42 (14)
C8—C7—C6	118.1 (3)	O3—S1—O1	107.80 (15)
C9—C8—C7	119.0 (3)	O2—S1—O1	109.46 (12)
C9—C8—H8	120.5

O1—Cu1—N1—C5	−51.2 (6)	C8—C9—C10—C11	−0.8 (5)
O5—Cu1—N1—C5	38.8 (2)	C9—C10—C11—C12	1.1 (5)
N2ⁱ—Cu1—N1—C5	−123.9 (2)	C9—C10—C11—C13	−176.4 (3)
O4ⁱⁱ—Cu1—N1—C5	138.9 (2)	C10—C11—C12—C7	0.1 (4)
O1—Cu1—N1—C1	123.0 (5)	C13—C11—C12—C7	177.4 (3)
O5—Cu1—N1—C1	−147.0 (2)	C8—C7—C12—C11	−1.6 (4)
N2ⁱ—Cu1—N1—C1	50.3 (2)	C6—C7—C12—C11	−179.6 (3)
O4ⁱⁱ—Cu1—N1—C1	−46.9 (2)	C14—N4—C13—O7	11.6 (5)
O5—Cu1—O1—S1	−2.5 (3)	C14—N4—C13—C11	−167.5 (3)
N1—Cu1—O1—S1	87.3 (6)	C12—C11—C13—O7	−167.7 (3)
N2ⁱ—Cu1—O1—S1	160.7 (3)	C10—C11—C13—O7	9.7 (5)
O4ⁱⁱ—Cu1—O1—S1	−103.0 (3)	C12—C11—C13—N4	11.4 (5)
C5—N1—C1—C2	2.9 (4)	C10—C11—C13—N4	−171.3 (3)
Cu1—N1—C1—C2	−171.7 (2)	C13—N4—C14—C15	−168.0 (3)
N1—C1—C2—C3	−0.7 (5)	C13—N4—C14—C18	13.9 (5)
C6—N3—C3—C4	−9.6 (5)	C18—C14—C15—C16	0.2 (5)
C6—N3—C3—C2	173.1 (3)	N4—C14—C15—C16	−178.0 (3)
C1—C2—C3—N3	175.6 (3)	C17—N2—C16—C15	−2.2 (4)
C1—C2—C3—C4	−1.9 (4)	Cu1ⁱ—N2—C16—C15	−176.3 (2)
N3—C3—C4—C5	−175.1 (3)	C14—C15—C16—N2	1.7 (5)
C2—C3—C4—C5	2.2 (4)	C16—N2—C17—C18	0.9 (5)
C1—N1—C5—C4	−2.6 (4)	Cu1ⁱ—N2—C17—C18	175.4 (2)
Cu1—N1—C5—C4	171.9 (2)	N2—C17—C18—C14	0.9 (5)
C3—C4—C5—N1	0.1 (5)	C15—C14—C18—C17	−1.5 (5)
C3—N3—C6—O6	−9.8 (5)	N4—C14—C18—C17	176.6 (3)
C3—N3—C6—C7	170.9 (3)	C20—N5—C19—O8	−173.9 (5)
O6—C6—C7—C12	150.7 (3)	C21—N5—C19—O8	4.0 (6)
N3—C6—C7—C12	−30.1 (4)	Cu1ⁱⁱ—O4—S1—O3	−161.85 (15)
O6—C6—C7—C8	−27.4 (4)	Cu1ⁱⁱ—O4—S1—O2	76.27 (18)
N3—C6—C7—C8	151.8 (3)	Cu1ⁱⁱ—O4—S1—O1	−43.6 (2)
C12—C7—C8—C9	1.9 (5)	Cu1—O1—S1—O4	125.2 (3)
C6—C7—C8—C9	180.0 (3)	Cu1—O1—S1—O3	−114.4 (3)
C7—C8—C9—C10	−0.7 (5)	Cu1—O1—S1—O2	4.8 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱⁱⁱ	0.86 (3)	2.03 (3)	2.867 (3)	164 (3)
N4—H4A···O3ⁱⁱⁱ	0.87 (3)	2.25 (3)	3.103 (4)	168 (3)
O5—H5A···O8^iv	0.82 (3)	1.81 (3)	2.626 (4)	179 (4)
O5—H5B···O2	0.81 (3)	1.90 (3)	2.684 (3)	164 (4)
C4—H4···O8	0.93	2.45	3.325 (4)	157
C18—H18···O6^v	0.93	2.55	3.277 (4)	136
C19—H19···O4^vi	0.93	2.47	3.286 (4)	146
C20—H20C···O3^vii	0.96	2.58	3.226 (6)	125

Symmetry codes: (iii) x, y−1, z; (iv) −x+1, −y+2, −z+1; (v) −x, −y+1, −z+1; (vi) x, y−1, z+1; (vii) −x, −y+3, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(SO₄)(C₁₈H₁₄N₄O₂)(H₂O)]·C₃H₇NO
M_r	569.06
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.389 (2), 11.092 (1), 12.105 (2)
α, β, γ (°)	63.47 (3), 79.75 (2), 71.08 (3)
V (Å³)	1179.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.07
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Rigaku Saturn 724 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.753, 0.814
No. of measured, independent and observed [I > 2σ(I)] reflections	14785, 5581, 4622
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.124, 1.07
No. of reflections	5581
No. of parameters	339
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.48

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱ	0.86 (3)	2.03 (3)	2.867 (3)	164 (3)
N4—H4A···O3ⁱ	0.87 (3)	2.25 (3)	3.103 (4)	168 (3)
O5—H5A···O8ⁱⁱ	0.82 (3)	1.81 (3)	2.626 (4)	179 (4)
O5—H5B···O2	0.81 (3)	1.90 (3)	2.684 (3)	164 (4)
C4—H4···O8	0.93	2.45	3.325 (4)	157
C18—H18···O6ⁱⁱⁱ	0.93	2.55	3.277 (4)	136
C19—H19···O4^iv	0.93	2.47	3.286 (4)	146
C20—H20C···O3^v	0.96	2.58	3.226 (6)	125

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

Acknowledgements

The authors are grateful to the Henan Center for Disease Control and Prevention for financial support and thank Professor Hong-Wei Hou of Zhengzhou University for his help.

References

Adarsh, N. N., Kumar, D. K. & Dastidar, P. (2009). CrystEngComm, 11, 792–802. Web of Science CSD CrossRef Google Scholar
Gong, Y., Zhou, Y. C., Li, J. H., Cao, R. & Qin, J. B. (2010). Dalton Trans. 39, 9923–9928. Web of Science CSD CrossRef CAS PubMed Google Scholar
Gong, Y., Zhou, Y. C., Liu, T. F., Lu, J., Proserpioc, D. M. & Cao, R. (2011). Chem. Commun. 47, 5982–5984. Web of Science CSD CrossRef CAS Google Scholar
Kim, K., Park, S., Park, K. M. & Lee, S. S. (2011). Cryst. Growth Des. 11, 4059–4067. Web of Science CSD CrossRef CAS Google Scholar
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 3| March 2013| Pages m150-m151

doi:10.1107/S1600536813003413

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[[[aqua­copper(II)]-bis­­[μ-N,N′-bis­­(pyridin-4-yl)isophthalamide]-[aqua­copper(II)]-di-μ-sulfato] di­methyl­formamide disolvate]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[[[aquacopper(II)]-bis[μ-N,N′-bis(pyridin-4-yl)isophthalamide]-[aquacopper(II)]-di-μ-sulfato] dimethylformamide disolvate]