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The title compound, {[Cu(C2H6NO3S)2(C10H8N2)]·C10H8N2·H2O}n, was obtained by the hydro­thermal reaction of Cu(CH3COO)2·2H2O, 4,4′-bipyridne and taurine at 380 K. The 4,4′-bipyridine ligands bridge CuII ions, forming polymeric chains, in which CuII ions and the bridging ligands lie on twofold axes. Two taurine anions chelate to the CuII ion by the terminal N and O atoms, completing the distorted octa­hedral coordination. The uncoordinated bipyridine molecule is located on an inversion center.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040900/xu6086sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040900/xu6086Isup2.hkl
Contains datablock I

CCDC reference: 296710

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.099
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C1B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1A PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C9 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.37 PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 4.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Several Schiff bases derived from taurine have recently been prepared in our laboratory (Zhang & Jiang, 2002; Zeng et al., 2003; Jiang et al., 2004) because of the important physiological properties of taurine. As part of our ongoing investigation on taurine derivatives, we report here the synthesis and crystal structure of the title taurine–copper(II) complex, (I).

The crystal structure of (I) consists of one-dimensional complex chains, coordinated 4,4-bipyridine (bipy) and water molecules. The bipy ligands bridge neighboring CuII ions, forming infinite polymeric chains along the crystallographic b axis (Fig. 1). The polymeric chain is located on a twofold axis. Two taurine anions chelate to the CuII ion by terminal N and O atoms to complete the distorted octahedral coordination. The longer Cu—O3 bond distance (Table 1) shows the typical Jahn–Teller distortion effect for the CuII ion. Within the bridging bipy ligand, the two pyridine rings are twisted to each other with a dihedral angle of 53.11 (4)°.

The bipy is located on an inversion center and displays a planar configuration. Weak C—H···O hydrogen bonding occurs between the bipy and the water molecules (Table 2). Classic O—H···O hydrogen bonding is also observed between the water and the complex chain.

Experimental top

A methanol solution (10 ml) of taurine (1.5 mmol) and KOH (1.5 mmol) was mixed with another methanol solution (10 ml) of Cu(CH3COO)2·2H2O (0.5 mmol). After stirring for 10 min, 4,4'-bipyridne (1 mmol) was added slowly to the mixture. It was then dropped into a 25 ml Teflon-stainless steel reactor and heated at 380 K for 5 d. After cooling the reactor to room temperature, single crystals of (I) were obtained (yield 65%). Analysis found (%): C 44.87, H 4.66, N 13.05, S 9.98; calculated (%): C 44.84, H 4.67, N 13.08, S 9.97. IR (KBr, ν cm−1): 1033.3, 1168.1, 1237.4 (–SO3), 3258.4, 3304.3 (ν N—H).

Refinement top

The methylene group of aminomethylenesulfonate is disordered over two sites with 0.5 site-occupancy factors. The water molecule is located close to the twofold axis and has a 0.5 site-occupancy factor. H atoms on N and O atoms were located in a difference Fourier map and refined as riding in their as-found relative positions, with Uiso(H) = 1.2Ueq(carrier). Other H atoms were placed in calculated positions, with C—H = 0.93 (aromatic) or 0.97 Å (methylene), and refined using a riding-model approximation, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A segment of the polymeric structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms) [symmetry codes: (A) −x, y, 1/2 − z; (B) x, 1 + y, z; (C) 1 − x, −y, 1 − z].
catena-Poly[[[bis(2-aminoethanesulfonato-κ2N,O)copper(II)]-µ-4,4'- bipyridine-κ2N:N'] 4,4'-bipyridine monohydrate]] top
Crystal data top
[Cu(C2H6NO3S)2(C10H8N2)]·C10H8N2·H2OF(000) = 666
Mr = 642.2Dx = 1.537 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 2887 reflections
a = 9.8647 (11) Åθ = 3.3–27.5°
b = 11.3846 (9) ŵ = 0.99 mm1
c = 12.9516 (14) ÅT = 293 K
β = 107.446 (5)°Prism, blue
V = 1387.6 (2) Å30.25 × 0.20 × 0.15 mm
Z = 2
Data collection top
Rigaku Mercury CCD
diffractometer
3176 independent reflections
Radiation source: fine-focus sealed tube2681 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ϕ and ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1112
Tmin = 0.775, Tmax = 0.860k = 1414
10598 measured reflectionsl = 1615
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.031P)2 + 1.3917P]
where P = (Fo2 + 2Fc2)/3
3176 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.42 e Å3
1 restraintΔρmin = 0.40 e Å3
Crystal data top
[Cu(C2H6NO3S)2(C10H8N2)]·C10H8N2·H2OV = 1387.6 (2) Å3
Mr = 642.2Z = 2
Monoclinic, P2/cMo Kα radiation
a = 9.8647 (11) ŵ = 0.99 mm1
b = 11.3846 (9) ÅT = 293 K
c = 12.9516 (14) Å0.25 × 0.20 × 0.15 mm
β = 107.446 (5)°
Data collection top
Rigaku Mercury CCD
diffractometer
3176 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2681 reflections with I > 2σ(I)
Tmin = 0.775, Tmax = 0.860Rint = 0.039
10598 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0471 restraint
wR(F2) = 0.099H-atom parameters constrained
S = 1.08Δρmax = 0.42 e Å3
3176 reflectionsΔρmin = 0.40 e Å3
208 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
xyzUiso*/UeqOcc. (<1)
Cu0.00000.37558 (3)0.25000.02478 (14)
S0.25875 (8)0.39859 (6)0.49274 (6)0.03598 (18)
N10.00000.1853 (2)0.25000.0332 (7)
N20.1844 (2)0.37126 (19)0.21701 (18)0.0325 (5)
H2A0.17910.42390.16580.039*
H2B0.18850.30420.18960.039*
N30.00000.5624 (2)0.25000.0280 (7)
N40.7300 (4)0.1558 (3)0.3845 (3)0.0790 (11)
O10.3188 (3)0.3010 (2)0.5593 (2)0.0904 (10)
O20.2828 (3)0.5085 (2)0.5489 (2)0.0729 (8)
O30.1092 (2)0.37865 (16)0.43436 (15)0.0370 (4)
O1W0.5829 (8)0.2895 (8)0.7232 (5)0.134 (3)0.50
H1C0.49580.29440.67910.161*0.50
H1D0.59360.29340.79610.161*0.50
C1A0.3188 (5)0.3414 (5)0.3031 (4)0.0278 (11)0.50
H1A10.39740.33840.27270.033*0.50
H1A20.31010.26520.33400.033*0.50
C2A0.3459 (7)0.4380 (6)0.3919 (6)0.0350 (15)0.50
H2A10.30930.51260.35910.042*0.50
H2A20.44720.44640.42650.042*0.50
C1B0.3085 (7)0.4331 (8)0.2996 (6)0.0589 (19)0.50
H1B10.38800.43870.27030.071*0.50
H1B20.27990.51230.31130.071*0.50
C2B0.3536 (8)0.3728 (8)0.4012 (7)0.053 (2)0.50
H2B10.45210.39320.43640.063*0.50
H2B20.35050.28910.38660.063*0.50
C30.0111 (3)0.6237 (2)0.1647 (2)0.0328 (6)
H30.01750.58270.10430.039*
C40.0134 (3)0.7442 (2)0.1622 (2)0.0359 (6)
H40.02390.78300.10180.043*
C50.00000.8084 (3)0.25000.0302 (8)
C60.0586 (3)0.1244 (2)0.1593 (2)0.0395 (7)
H60.09970.16550.09560.047*
C70.0606 (3)0.0027 (2)0.1561 (3)0.0424 (7)
H70.10250.03610.09120.051*
C80.00000.0610 (3)0.25000.0358 (9)
C90.5482 (3)0.0322 (2)0.4758 (3)0.0414 (7)
C100.5921 (4)0.1457 (3)0.5069 (3)0.0540 (9)
H100.56260.18300.56020.065*
C110.6802 (4)0.2032 (3)0.4582 (4)0.0678 (12)
H110.70580.28020.47900.081*
C120.6910 (5)0.0463 (4)0.3565 (4)0.0864 (15)
H120.72620.01020.30540.104*
C130.6007 (4)0.0176 (3)0.3989 (3)0.0671 (11)
H130.57560.09390.37540.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0296 (2)0.0165 (2)0.0310 (3)0.0000.01326 (19)0.000
S0.0381 (4)0.0362 (4)0.0315 (4)0.0053 (3)0.0072 (3)0.0069 (3)
N10.0352 (18)0.0186 (14)0.046 (2)0.0000.0124 (15)0.000
N20.0344 (12)0.0353 (11)0.0311 (12)0.0008 (9)0.0149 (10)0.0025 (10)
N30.0365 (17)0.0196 (13)0.0311 (16)0.0000.0150 (14)0.000
N40.086 (2)0.0542 (19)0.122 (3)0.0166 (17)0.070 (2)0.006 (2)
O10.084 (2)0.0679 (18)0.093 (2)0.0237 (15)0.0139 (17)0.0292 (16)
O20.0695 (17)0.0516 (14)0.106 (2)0.0207 (12)0.0397 (16)0.0400 (14)
O30.0366 (11)0.0424 (11)0.0327 (11)0.0007 (8)0.0114 (9)0.0010 (8)
O1W0.126 (6)0.192 (8)0.057 (4)0.038 (6)0.015 (4)0.033 (5)
C1A0.026 (3)0.031 (3)0.030 (3)0.005 (2)0.013 (2)0.010 (2)
C2A0.034 (3)0.036 (3)0.037 (4)0.009 (3)0.014 (3)0.013 (3)
C1B0.037 (4)0.080 (6)0.068 (5)0.009 (4)0.029 (4)0.010 (4)
C2B0.030 (3)0.067 (5)0.058 (5)0.007 (4)0.009 (3)0.008 (5)
C30.0472 (16)0.0235 (12)0.0312 (14)0.0006 (11)0.0170 (13)0.0008 (10)
C40.0530 (18)0.0242 (12)0.0330 (15)0.0001 (11)0.0167 (13)0.0047 (11)
C50.0309 (19)0.0196 (16)0.039 (2)0.0000.0092 (17)0.000
C60.0476 (17)0.0238 (12)0.0429 (17)0.0017 (12)0.0073 (14)0.0014 (12)
C70.0531 (19)0.0247 (13)0.0440 (17)0.0009 (12)0.0062 (15)0.0031 (12)
C80.038 (2)0.0234 (18)0.047 (2)0.0000.0141 (19)0.000
C90.0352 (15)0.0318 (14)0.059 (2)0.0020 (12)0.0173 (14)0.0101 (14)
C100.053 (2)0.0329 (16)0.088 (3)0.0010 (14)0.0392 (19)0.0029 (16)
C110.067 (2)0.0331 (16)0.119 (4)0.0088 (16)0.051 (3)0.006 (2)
C120.109 (4)0.069 (3)0.112 (4)0.022 (3)0.080 (3)0.012 (3)
C130.083 (3)0.047 (2)0.089 (3)0.0233 (19)0.053 (2)0.009 (2)
Geometric parameters (Å, º) top
Cu—N12.166 (3)C2A—H2A20.9700
Cu—N21.990 (2)C1B—C2B1.432 (11)
Cu—N2i1.990 (2)C1B—H1B10.9700
Cu—N32.127 (3)C1B—H1B20.9700
Cu—O3i2.3067 (19)C2B—H2B10.9700
Cu—O32.3067 (19)C2B—H2B20.9700
S—O11.422 (3)C3—C41.373 (3)
S—O21.431 (2)C3—H30.9300
S—O31.460 (2)C4—C51.391 (3)
S—C2B1.741 (8)C4—H40.9300
S—C2A1.822 (7)C5—C4i1.391 (3)
N1—C61.336 (3)C5—C8ii1.487 (5)
N1—C6i1.336 (3)C6—C71.386 (4)
N2—C1A1.493 (6)C6—H60.9300
N2—C1B1.534 (8)C7—C81.388 (3)
N2—H2A0.8838C7—H70.9300
N2—H2B0.8482C8—C7i1.388 (3)
N3—C3i1.338 (3)C8—C5iii1.487 (5)
N3—C31.338 (3)C9—C131.375 (5)
N4—C111.313 (5)C9—C101.384 (4)
N4—C121.323 (5)C9—C9iv1.482 (6)
O1W—H1C0.8790C10—C111.381 (5)
O1W—H1D0.9192C10—H100.9300
C1A—C2A1.556 (8)C11—H110.9300
C1A—H1A10.9700C12—C131.384 (5)
C1A—H1A20.9700C12—H120.9300
C2A—H2A10.9700C13—H130.9300
N2—Cu—N2i177.17 (13)S—C2A—H2A1109.7
N2—Cu—N391.42 (6)C1A—C2A—H2A2109.7
N2i—Cu—N391.42 (6)S—C2A—H2A2109.7
N2—Cu—N188.58 (6)H2A1—C2A—H2A2108.2
N2i—Cu—N188.58 (6)C2B—C1B—N2112.6 (6)
N3—Cu—N1180.0C2B—C1B—H1B1109.1
N2—Cu—O3i87.22 (8)N2—C1B—H1B1109.1
N2i—Cu—O3i92.83 (8)C2B—C1B—H1B2109.1
N3—Cu—O3i89.13 (5)N2—C1B—H1B2109.1
N1—Cu—O3i90.87 (5)H1B1—C1B—H1B2107.8
N2—Cu—O392.83 (8)C1B—C2B—S117.5 (6)
N2i—Cu—O387.22 (8)C1B—C2B—H2B1107.9
N3—Cu—O389.13 (5)S—C2B—H2B1107.9
N1—Cu—O390.87 (5)C1B—C2B—H2B2107.9
O3i—Cu—O3178.27 (9)S—C2B—H2B2107.9
O1—S—O2113.56 (19)H2B1—C2B—H2B2107.2
O1—S—O3111.42 (15)N3—C3—C4123.1 (3)
O2—S—O3112.77 (14)N3—C3—H3118.4
O1—S—C2B94.0 (3)C4—C3—H3118.4
O2—S—C2B116.9 (3)C3—C4—C5119.9 (3)
O3—S—C2B106.7 (3)C3—C4—H4120.0
O1—S—C2A115.3 (3)C5—C4—H4120.0
O2—S—C2A96.1 (2)C4—C5—C4i116.7 (3)
O3—S—C2A106.7 (2)C4—C5—C8ii121.67 (16)
C6—N1—C6i117.5 (3)C4i—C5—C8ii121.67 (16)
C6—N1—Cu121.25 (16)N1—C6—C7122.9 (3)
C6i—N1—Cu121.25 (16)N1—C6—H6118.5
C1A—N2—Cu120.6 (2)C7—C6—H6118.5
C1B—N2—Cu115.4 (3)C6—C7—C8119.8 (3)
C1A—N2—H2A123.7C6—C7—H7120.1
C1B—N2—H2A93.9C8—C7—H7120.1
Cu—N2—H2A107.0C7i—C8—C7117.0 (3)
C1A—N2—H2B88.0C7i—C8—C5iii121.51 (17)
C1B—N2—H2B125.2C7—C8—C5iii121.51 (17)
Cu—N2—H2B105.9C13—C9—C10116.3 (3)
H2A—N2—H2B107.2C13—C9—C9iv122.1 (3)
C3i—N3—C3117.2 (3)C10—C9—C9iv121.6 (4)
C3i—N3—Cu121.42 (15)C11—C10—C9119.6 (3)
C3—N3—Cu121.42 (15)C11—C10—H10120.2
C11—N4—C12116.4 (3)C9—C10—H10120.2
S—O3—Cu128.64 (12)N4—C11—C10124.1 (3)
H1C—O1W—H1D117.0N4—C11—H11118.0
N2—C1A—C2A107.9 (4)C10—C11—H11118.0
N2—C1A—H1A1110.1N4—C12—C13123.7 (4)
C2A—C1A—H1A1110.1N4—C12—H12118.2
N2—C1A—H1A2110.1C13—C12—H12118.2
C2A—C1A—H1A2110.1C9—C13—C12119.8 (3)
H1A1—C1A—H1A2108.4C9—C13—H13120.1
C1A—C2A—S110.0 (4)C12—C13—H13120.1
C1A—C2A—H2A1109.7
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+1, z; (iii) x, y1, z; (iv) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1C···O10.881.962.827 (8)169
O1W—H1D···O1v0.921.812.693 (7)159
N2—H2A···O2vi0.882.202.971 (3)145
N2—H2B···N4vii0.852.213.021 (4)160
Symmetry codes: (v) x+1, y, z+3/2; (vi) x, y+1, z1/2; (vii) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formula[Cu(C2H6NO3S)2(C10H8N2)]·C10H8N2·H2O
Mr642.2
Crystal system, space groupMonoclinic, P2/c
Temperature (K)293
a, b, c (Å)9.8647 (11), 11.3846 (9), 12.9516 (14)
β (°) 107.446 (5)
V3)1387.6 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.99
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerRigaku Mercury CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.775, 0.860
No. of measured, independent and
observed [I > 2σ(I)] reflections
10598, 3176, 2681
Rint0.039
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.099, 1.08
No. of reflections3176
No. of parameters208
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.42, 0.40

Computer programs: CrystalClear (Rigaku, 2000), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
Cu—N12.166 (3)Cu—N32.127 (3)
Cu—N21.990 (2)Cu—O32.3067 (19)
N2—Cu—N2i177.17 (13)N2—Cu—N391.42 (6)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1C···O10.881.962.827 (8)169
O1W—H1D···O1ii0.921.812.693 (7)159
N2—H2A···O2iii0.882.202.971 (3)145
N2—H2B···N4iv0.852.213.021 (4)160
Symmetry codes: (ii) x+1, y, z+3/2; (iii) x, y+1, z1/2; (iv) x+1, y, z+1/2.
 

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