Tetra­aqua­bis[4-(4-pyrid­yl)pyrimidine-2-sulfonato]copper(II) dihydrate

Li, L.; Xu, G.; Zhu, H.-B.

doi:10.1107/S1600536809011738

metal-organic compounds

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Volume 65| Part 5| May 2009| Page m476

doi:10.1107/S1600536809011738

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Tetraaquabis[4-(4-pyridyl)pyrimidine-2-sulfonato]copper(II) dihydrate

Lei Li,^a Gang Xu ^a and Hai-Bin Zhu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing, People's Republic of China
^*Correspondence e-mail: zhuhaibin@seu.edu.cn

(Received 27 March 2009; accepted 30 March 2009; online 2 April 2009)

In the title complex, [Cu(C₉H₆N₃O₃S)₂(H₂O)₄]·2H₂O, the Cu^II atom lies on an inversion centre and is coordinated by four water molecules in equatorial positions and two N atoms from two 4-(4-pyridyl)pyrimidine-2-sulfonate ligands in apical positions. The asymmetric unit contains half of the complex and one free water molecule. The water molecules, including the uncoordinated water molecules, and sulfonate O atoms are involved in O—H⋯O and O—H⋯N hydrogen-bonding interactions.

Related literature

For coordination complexes with pyridine-2 sulfonate ligands, see: Kimura et al. (1999 ); Lobana et al. (2004 ). For coordination complexes with 4-(pyridin-2-yl)pyrimidine-2-sulfonate, see: Zhu et al. (2007 ).

Experimental

Crystal data

[Cu(C₉H₆N₃O₃S)₂(H₂O)₄]·2H₂O
M_r = 644.09
Monoclinic, P 2₁ /n
a = 8.0727 (11) Å
b = 12.1502 (16) Å
c = 13.4911 (17) Å
β = 95.123 (2)°
V = 1318.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 298 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.884, T_max = 0.920
7057 measured reflections
2459 independent reflections
1786 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.00
2459 reflections
197 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯O2ⁱ	0.83 (7)	2.60 (7)	3.130 (9)	123 (7)
O1W—H2W⋯N2ⁱ	0.83 (7)	2.27 (4)	3.047 (10)	158 (7)
O2W—H4W⋯O3ⁱⁱ	0.82 (7)	1.91 (7)	2.734 (9)	175 (11)
O2W—H3W⋯O2ⁱ	0.83 (6)	1.93 (6)	2.756 (9)	169 (10)
O3W—H5W⋯O2ⁱⁱⁱ	0.82 (6)	2.47 (7)	2.879 (10)	111 (6)
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011738/at2756sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011738/at2756Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of some heterocyclic sulfonate ligands has been examined in several reports (Kimura et al., 1999; Lobana et al. 2004). In our previous work (Zhu et al., 2007), we have also studied divalent metal coordination complexes with the heterocyclic sulfonate ligand, namely 4-(pyridin-2-yl)pyrimidine-2-sulfonate. Herein, we report the copper(II) coordination complex with its analog, viz 4-(pyridin-4-yl)pyrimidine-2-sulfonate.

The coordination geometry about Cu(II) center is shown in Fig.1. The Cu(II) center adopts an octahedral coordination geometry. The equtorial plane around the copper ion is defined by four water molecules and the apical positions are occupied by two nitrogen atoms belonging to two heterocyclic sulfonate ligands. In the title complex, the Cu^IIatom lies on an inversion centre and the asymmetric unit contains half of the complex and one free water molecule. The Cu—O bond lengths are in the range of 2.094 (6) to 2.289 (7) Å and the Cu—N bond distance is 2.008 (7) Å. The coordinated water molecules, the guest water molecules and the free sulfonato oxgen atoms are involved in the hydrogen bonding interactions (Table 1).

Related literature top

For coordination complexes with pyridine-2 sulfonate ligands, see: Kimura et al. (1999); Lobana et al. (2004). For coordination complexes with 4-(pyridin-2-yl)pyrimidine-2-sulfonate, see: Zhu et al. (2007).

Experimental top

The mixture of Cu(NO₃)₂(0.1 mmol), sodium 4-(pyridin-4-yl)pyrimidine-2-sulfonate (0.2 mmol) in 6 mL of H₂O was stirred for 20 min at room temperature. After filtration, the mother liquid was stood for three days to give the green crystals suitable for X-ray diffraction analysis.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The coordination environment around Cu(II) in the title complex with the atom-labeling scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.

Tetraaquabis[4-(4-pyridyl)pyrimidine-2-sulfonato]copper(II) dihydrate top

Crystal data top

[Cu(C₉H₆N₃O₃S)₂(H₂O)₄]·2H₂O	F(000) = 662
M_r = 644.09	D_x = 1.623 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2459 reflections
a = 8.0727 (11) Å	θ = 2.3–25.5°
b = 12.1502 (16) Å	µ = 1.06 mm⁻¹
c = 13.4911 (17) Å	T = 298 K
β = 95.123 (2)°	Block, blue
V = 1318.0 (3) Å³	0.12 × 0.10 × 0.08 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	2459 independent reflections
Radiation source: fine-focus sealed tube	1786 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.884, T_max = 0.920	k = −14→12
7057 measured reflections	l = −16→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.044P)²] where P = (F_o² + 2F_c²)/3
2459 reflections	(Δ/σ)_max < 0.001
197 parameters	Δρ_max = 0.33 e Å⁻³
9 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Cu(C₉H₆N₃O₃S)₂(H₂O)₄]·2H₂O	V = 1318.0 (3) Å³
M_r = 644.09	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0727 (11) Å	µ = 1.06 mm⁻¹
b = 12.1502 (16) Å	T = 298 K
c = 13.4911 (17) Å	0.12 × 0.10 × 0.08 mm
β = 95.123 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2459 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1786 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.920	R_int = 0.079
7057 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	9 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.33 e Å⁻³
2459 reflections	Δρ_min = −0.37 e Å⁻³
197 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	1.0000	0.5000	0.5000	0.0309 (6)
S1	0.7319 (3)	−0.21520 (17)	0.67968 (16)	0.0350 (7)
C1	0.7066 (10)	−0.1463 (7)	0.5611 (6)	0.0296 (19)
C2	0.6103 (12)	−0.1450 (8)	0.3997 (7)	0.044 (2)
H2	0.5582	−0.1793	0.3436	0.053*
C3	0.6619 (11)	−0.0369 (7)	0.3918 (7)	0.039 (2)
H3	0.6460	0.0009	0.3318	0.047*
C4	0.7378 (10)	0.0130 (7)	0.4763 (6)	0.030 (2)
C5	0.8025 (10)	0.1277 (6)	0.4787 (6)	0.0285 (19)
C6	0.7554 (11)	0.2040 (7)	0.4050 (6)	0.037 (2)
H6	0.6823	0.1839	0.3508	0.044*
C7	0.8170 (11)	0.3090 (7)	0.4123 (7)	0.037 (2)
H7	0.7832	0.3590	0.3624	0.044*
C8	0.9733 (11)	0.2692 (7)	0.5587 (6)	0.032 (2)
H8	1.0496	0.2910	0.6107	0.038*
C9	0.9145 (11)	0.1623 (7)	0.5569 (6)	0.033 (2)
H9	0.9497	0.1137	0.6077	0.040*
H1W	0.707 (11)	0.500 (5)	0.480 (5)	0.080*
H2W	0.693 (10)	0.617 (5)	0.471 (6)	0.080*
H3W	0.881 (8)	0.562 (5)	0.658 (7)	0.080*
H4W	0.931 (11)	0.455 (5)	0.681 (6)	0.080*
H5W	0.531 (10)	0.463 (9)	0.341 (4)	0.080*
H6W	0.631 (7)	0.518 (8)	0.286 (6)	0.080*
N1	0.7598 (8)	−0.0431 (6)	0.5630 (5)	0.0307 (17)
N2	0.6322 (9)	−0.2021 (6)	0.4845 (5)	0.0386 (19)
N3	0.9233 (9)	0.3430 (5)	0.4875 (5)	0.0305 (16)
O1	0.8989 (8)	−0.1917 (6)	0.7206 (5)	0.0557 (19)
O2	0.7032 (8)	−0.3316 (5)	0.6583 (5)	0.0497 (18)
O3	0.6036 (8)	−0.1672 (5)	0.7337 (4)	0.0464 (17)
O1W	0.7375 (9)	0.5611 (6)	0.4501 (6)	0.059 (2)
O2W	0.9469 (8)	0.5109 (5)	0.6488 (5)	0.0445 (17)
O3W	0.5402 (9)	0.4870 (7)	0.2846 (6)	0.062 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0474 (10)	0.0141 (8)	0.0317 (9)	−0.0047 (7)	0.0059 (7)	0.0003 (6)
S1	0.0505 (15)	0.0172 (12)	0.0378 (14)	0.0007 (10)	0.0069 (11)	0.0024 (9)
C1	0.037 (5)	0.019 (4)	0.033 (5)	0.000 (4)	0.008 (4)	−0.003 (4)
C2	0.059 (6)	0.033 (6)	0.039 (6)	−0.009 (5)	−0.004 (5)	−0.007 (5)
C3	0.056 (6)	0.024 (5)	0.036 (5)	−0.006 (4)	−0.001 (4)	0.005 (4)
C4	0.035 (5)	0.021 (5)	0.034 (5)	0.000 (4)	0.003 (4)	−0.001 (4)
C5	0.037 (5)	0.017 (4)	0.032 (5)	−0.003 (4)	0.005 (4)	0.001 (4)
C6	0.043 (5)	0.027 (5)	0.038 (5)	−0.005 (4)	−0.006 (4)	0.002 (4)
C7	0.046 (5)	0.022 (5)	0.040 (5)	−0.001 (4)	−0.004 (4)	0.010 (4)
C8	0.044 (5)	0.021 (5)	0.030 (5)	−0.004 (4)	0.002 (4)	−0.002 (4)
C9	0.049 (5)	0.018 (4)	0.033 (5)	−0.001 (4)	0.003 (4)	0.006 (4)
N1	0.044 (4)	0.017 (4)	0.032 (4)	−0.002 (3)	0.005 (3)	0.001 (3)
N2	0.055 (5)	0.023 (4)	0.038 (4)	−0.007 (4)	0.002 (4)	0.000 (3)
N3	0.042 (4)	0.018 (4)	0.032 (4)	−0.001 (3)	0.005 (3)	0.002 (3)
O1	0.056 (4)	0.046 (5)	0.062 (4)	−0.001 (3)	−0.011 (3)	0.016 (4)
O2	0.080 (5)	0.015 (3)	0.056 (4)	−0.001 (3)	0.016 (4)	0.003 (3)
O3	0.064 (4)	0.037 (4)	0.040 (4)	0.008 (3)	0.015 (3)	−0.002 (3)
O1W	0.068 (5)	0.027 (4)	0.083 (5)	0.005 (4)	0.007 (4)	−0.012 (4)
O2W	0.061 (4)	0.024 (4)	0.050 (4)	0.003 (3)	0.016 (3)	0.006 (3)
O3W	0.059 (5)	0.058 (5)	0.067 (5)	−0.005 (4)	−0.004 (4)	0.009 (4)

Geometric parameters (Å, º) top

Cu1—N3	2.008 (7)	C4—N1	1.352 (10)
Cu1—N3ⁱ	2.008 (7)	C4—C5	1.487 (11)
Cu1—O2W	2.094 (6)	C5—C6	1.388 (11)
Cu1—O2Wⁱ	2.094 (6)	C5—C9	1.391 (11)
Cu1—O1W	2.289 (7)	C6—C7	1.370 (12)
Cu1—O1Wⁱ	2.289 (7)	C6—H6	0.9300
Cu1—H1W	2.36 (9)	C7—N3	1.335 (11)
Cu1—H3W	2.53 (7)	C7—H7	0.9300
S1—O1	1.439 (7)	C8—N3	1.349 (10)
S1—O3	1.442 (6)	C8—C9	1.382 (11)
S1—O2	1.458 (6)	C8—H8	0.9300
S1—C1	1.801 (8)	C9—H9	0.9300
C1—N1	1.324 (10)	O1W—H1W	0.89 (3)
C1—N2	1.334 (10)	O1W—H2W	0.83 (7)
C2—N2	1.336 (11)	O2W—H3W	0.83 (6)
C2—C3	1.385 (12)	O2W—H4W	0.82 (7)
C2—H2	0.9300	O3W—H5W	0.82 (6)
C3—C4	1.384 (12)	O3W—H6W	0.82 (7)
C3—H3	0.9300

N3—Cu1—N3ⁱ	180.000 (1)	N2—C2—C3	122.7 (8)
N3—Cu1—O2W	93.0 (3)	N2—C2—H2	118.7
N3ⁱ—Cu1—O2W	87.0 (3)	C3—C2—H2	118.6
N3—Cu1—O2Wⁱ	87.0 (3)	C2—C3—C4	117.8 (8)
N3ⁱ—Cu1—O2Wⁱ	93.0 (3)	C2—C3—H3	121.1
O2W—Cu1—O2Wⁱ	180.000 (1)	C4—C3—H3	121.1
N3—Cu1—O1W	90.7 (3)	N1—C4—C3	120.3 (8)
N3ⁱ—Cu1—O1W	89.3 (3)	N1—C4—C5	115.8 (7)
O2W—Cu1—O1W	89.9 (3)	C3—C4—C5	123.9 (8)
O2Wⁱ—Cu1—O1W	90.1 (3)	C6—C5—C9	117.3 (8)
N3—Cu1—O1Wⁱ	89.3 (3)	C6—C5—C4	122.5 (8)
N3ⁱ—Cu1—O1Wⁱ	90.7 (3)	C9—C5—C4	120.2 (7)
O2W—Cu1—O1Wⁱ	90.1 (3)	C7—C6—C5	119.7 (8)
O2Wⁱ—Cu1—O1Wⁱ	89.9 (3)	C7—C6—H6	120.1
O1W—Cu1—O1Wⁱ	180.000 (1)	C5—C6—H6	120.1
N3—Cu1—H1W	72.1 (15)	N3—C7—C6	123.2 (8)
N3ⁱ—Cu1—H1W	107.9 (15)	N3—C7—H7	118.5
O2W—Cu1—H1W	79.5 (18)	C6—C7—H7	118.4
O2Wⁱ—Cu1—H1W	100.5 (18)	N3—C8—C9	122.1 (8)
O1Wⁱ—Cu1—H1W	158.0 (4)	N3—C8—H8	119.0
N3—Cu1—H3W	102.5 (19)	C9—C8—H8	119.0
N3ⁱ—Cu1—H3W	77.5 (19)	C8—C9—C5	119.8 (8)
O2W—Cu1—H3W	17.7 (12)	C8—C9—H9	120.1
O2Wⁱ—Cu1—H3W	162.3 (12)	C5—C9—H9	120.1
O1W—Cu1—H3W	75.0 (16)	C1—N1—C4	116.4 (7)
O1Wⁱ—Cu1—H3W	105.0 (16)	C1—N2—C2	114.6 (8)
H1W—Cu1—H3W	69 (3)	C8—N3—C7	117.9 (7)
O1—S1—O3	114.6 (4)	C8—N3—Cu1	120.1 (6)
O1—S1—O2	113.3 (4)	C7—N3—Cu1	122.0 (6)
O3—S1—O2	112.6 (4)	Cu1—O1W—H1W	83 (6)
O1—S1—C1	106.0 (4)	Cu1—O1W—H2W	126 (7)
O3—S1—C1	103.4 (4)	H1W—O1W—H2W	112 (4)
O2—S1—C1	105.8 (4)	Cu1—O2W—H3W	113 (6)
N1—C1—N2	128.2 (8)	Cu1—O2W—H4W	121 (7)
N1—C1—S1	114.4 (6)	H3W—O2W—H4W	114 (8)
N2—C1—S1	117.4 (6)	H5W—O3W—H6W	107 (8)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O2ⁱⁱ	0.83 (7)	2.60 (7)	3.130 (9)	123 (7)
O1W—H2W···N2ⁱⁱ	0.83 (7)	2.27 (4)	3.047 (10)	158 (7)
O2W—H4W···O3ⁱⁱⁱ	0.82 (7)	1.91 (7)	2.734 (9)	175 (11)
O2W—H3W···O2ⁱⁱ	0.83 (6)	1.93 (6)	2.756 (9)	169 (10)
O2W—H3W···S1ⁱⁱ	0.83 (6)	2.99 (4)	3.794 (7)	163 (7)
O3W—H5W···O2^iv	0.82 (6)	2.47 (7)	2.879 (10)	111 (6)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₉H₆N₃O₃S)₂(H₂O)₄]·2H₂O
M_r	644.09
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.0727 (11), 12.1502 (16), 13.4911 (17)
β (°)	95.123 (2)
V (Å³)	1318.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.884, 0.920
No. of measured, independent and observed [I > 2σ(I)] reflections	7057, 2459, 1786
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.00
No. of reflections	2459
No. of parameters	197
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.37

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O2ⁱ	0.83 (7)	2.60 (7)	3.130 (9)	123 (7)
O1W—H2W···N2ⁱ	0.83 (7)	2.27 (4)	3.047 (10)	158 (7)
O2W—H4W···O3ⁱⁱ	0.82 (7)	1.91 (7)	2.734 (9)	175 (11)
O2W—H3W···O2ⁱ	0.83 (6)	1.93 (6)	2.756 (9)	169 (10)
O2W—H3W···S1ⁱ	0.83 (6)	2.99 (4)	3.794 (7)	163 (7)
O3W—H5W···O2ⁱⁱⁱ	0.82 (6)	2.47 (7)	2.879 (10)	111 (6)

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

Acknowledgements

The authors acknowledge finanical support from the National Natural Science Foundation of China (No. 20801011) and the Young Teachers' Starting Fund of Southeast University.

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