(2,2'-Bipyridyl-κN,N')chlorido(dl-threoninato-κN,O)copper(II) monohydrate.

In the title compound, [Cu(C(4)H(8)NO(3))Cl(C(10)H(8)N(2))]·H(2)O, the Cu(II) atom is in a slightly distorted square-pyramidal coordination geometry with the basal plane defined by the two N atoms of the bipyridine ligand and the N and O atoms from the threoninate ion and the apical site occupied by the Cl atom. In the crystal, inter-molecular O-H⋯O, N-H⋯O, O-H⋯Cl, C-H⋯O and C-H⋯Cl inter-actions link the mol-ecules into a three-dimensional network. A π-π inter-action with a centroid-centroid distance of 3.461 (1) Å is also present.

Related literature

For background to superoxide dismutase activity, see: Kumar & Arunachalam (2007 ▶); Patel et al. (2006 ▶); Rao et al. (2007 ▶); Zhang et al. (2004 ▶). For a related structure, see: Tan et al. (2010 ▶).

Experimental

Crystal data

[Cu(C4H8NO3)Cl(C10H8N2)]·H2O

M = 391.30

Monoclinic,

a = 7.4825 (1) Å

b = 12.0378 (2) Å

c = 18.2083 (3) Å

β = 99.097 (1)°

V = 1619.44 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.54 mm−1

T = 297 K

0.39 × 0.33 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.585, T max = 0.864

14209 measured reflections

3767 independent reflections

3262 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.05

3767 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002583/is2663sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002583/is2663Isup2.hkl

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

[Cu(C4H8NO3)Cl(C10H8N2)]·H2O	F(000) = 804
Mr = 391.30	Dx = 1.605 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6390 reflections
a = 7.4825 (1) Å	θ = 2.3–27.7°
b = 12.0378 (2) Å	µ = 1.54 mm−1
c = 18.2083 (3) Å	T = 297 K
β = 99.097 (1)°	Block, blue
V = 1619.44 (4) Å3	0.39 × 0.33 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3767 independent reflections
Radiation source: fine-focus sealed tube	3262 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 27.7°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.585, Tmax = 0.864	k = −15→15
14209 measured reflections	l = −22→23

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0357P)2 + 1.3397P] where P = (Fo2 + 2Fc2)/3
3767 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.21099 (4)	0.51646 (2)	0.150342 (15)	0.03011 (9)
Cl1	0.50867 (8)	0.61287 (6)	0.20278 (4)	0.04414 (16)
O1	0.0535 (2)	0.63696 (14)	0.17196 (9)	0.0410 (4)
O2	−0.0305 (3)	0.72701 (15)	0.26746 (11)	0.0485 (5)
O3	−0.1859 (3)	0.46636 (18)	0.29026 (12)	0.0496 (5)
N1	0.1999 (2)	0.57032 (16)	0.04640 (10)	0.0313 (4)
N2	0.3031 (2)	0.37847 (15)	0.10406 (10)	0.0311 (4)
N3	0.1738 (3)	0.45802 (17)	0.24897 (11)	0.0323 (4)
C1	0.1465 (3)	0.6719 (2)	0.02282 (15)	0.0426 (6)
H1A	0.1111	0.7221	0.0565	0.051*
C2	0.1426 (4)	0.7044 (2)	−0.04996 (15)	0.0489 (7)
H2A	0.1038	0.7753	−0.0652	0.059*
C3	0.1965 (4)	0.6308 (3)	−0.09978 (14)	0.0471 (6)
H3A	0.1946	0.6513	−0.1491	0.056*
C4	0.2534 (3)	0.5266 (2)	−0.07581 (13)	0.0411 (6)
H4A	0.2920	0.4760	−0.1086	0.049*
C5	0.2525 (3)	0.49774 (19)	−0.00186 (12)	0.0301 (5)
C6	0.3081 (3)	0.38790 (19)	0.03022 (12)	0.0310 (5)
C7	0.3610 (3)	0.3007 (2)	−0.01053 (14)	0.0414 (6)
H7A	0.3630	0.3085	−0.0612	0.050*
C8	0.4109 (4)	0.2015 (2)	0.02508 (17)	0.0484 (6)
H8A	0.4470	0.1417	−0.0014	0.058*
C9	0.4068 (4)	0.1920 (2)	0.10013 (16)	0.0446 (6)
H9A	0.4409	0.1261	0.1251	0.054*
C10	0.3511 (3)	0.2820 (2)	0.13779 (14)	0.0381 (5)
H10A	0.3469	0.2752	0.1884	0.046*
C11	0.0373 (3)	0.64663 (19)	0.24007 (14)	0.0351 (5)
C12	0.1085 (3)	0.5511 (2)	0.29117 (13)	0.0339 (5)
H12A	0.2128	0.5791	0.3256	0.041*
C13	−0.0346 (4)	0.5158 (2)	0.33788 (14)	0.0407 (6)
H13A	−0.0767	0.5817	0.3617	0.049*
C14	0.0338 (5)	0.4324 (3)	0.39667 (17)	0.0614 (8)
H14A	−0.0561	0.4205	0.4281	0.092*
H14B	0.1429	0.4596	0.4260	0.092*
H14C	0.0584	0.3635	0.3736	0.092*
O1W	0.5123 (3)	0.36924 (19)	0.34690 (13)	0.0643 (6)
H1W1	0.6010	0.3869	0.3342	0.096*
H2W1	0.5185	0.3006	0.3382	0.096*
H1N3	0.098 (4)	0.405 (2)	0.2438 (14)	0.033 (7)*
H2N3	0.264 (4)	0.428 (2)	0.2692 (16)	0.042 (8)*
H1O3	−0.246 (5)	0.523 (3)	0.268 (2)	0.064 (11)*

	U11	U22	U33	U12	U13	U23
Cu1	0.03619 (16)	0.03037 (15)	0.02525 (15)	0.00142 (11)	0.00949 (11)	−0.00088 (11)
Cl1	0.0391 (3)	0.0492 (4)	0.0433 (3)	−0.0077 (3)	0.0043 (2)	−0.0089 (3)
O1	0.0500 (10)	0.0394 (9)	0.0360 (9)	0.0098 (8)	0.0146 (8)	0.0018 (7)
O2	0.0594 (11)	0.0371 (9)	0.0529 (11)	0.0046 (8)	0.0214 (9)	−0.0086 (8)
O3	0.0383 (10)	0.0506 (12)	0.0613 (13)	−0.0045 (9)	0.0120 (9)	0.0059 (10)
N1	0.0314 (9)	0.0358 (10)	0.0264 (9)	−0.0004 (8)	0.0038 (7)	0.0018 (8)
N2	0.0334 (9)	0.0323 (9)	0.0284 (9)	−0.0017 (8)	0.0074 (7)	0.0000 (8)
N3	0.0340 (10)	0.0322 (10)	0.0318 (10)	−0.0010 (9)	0.0087 (8)	0.0000 (8)
C1	0.0444 (13)	0.0397 (13)	0.0442 (14)	0.0064 (11)	0.0084 (11)	0.0057 (11)
C2	0.0480 (15)	0.0513 (16)	0.0450 (15)	0.0035 (12)	0.0002 (12)	0.0189 (13)
C3	0.0434 (14)	0.0672 (18)	0.0286 (12)	−0.0052 (13)	0.0000 (10)	0.0143 (12)
C4	0.0388 (12)	0.0556 (16)	0.0283 (12)	−0.0054 (11)	0.0037 (10)	−0.0008 (11)
C5	0.0273 (10)	0.0385 (12)	0.0239 (10)	−0.0059 (9)	0.0025 (8)	−0.0022 (9)
C6	0.0273 (10)	0.0367 (12)	0.0297 (11)	−0.0046 (9)	0.0069 (8)	−0.0040 (9)
C7	0.0449 (13)	0.0467 (14)	0.0339 (13)	−0.0029 (11)	0.0105 (10)	−0.0108 (11)
C8	0.0500 (15)	0.0401 (14)	0.0576 (17)	0.0005 (12)	0.0157 (13)	−0.0156 (13)
C9	0.0458 (14)	0.0355 (13)	0.0540 (16)	0.0019 (11)	0.0127 (12)	0.0035 (12)
C10	0.0411 (12)	0.0370 (12)	0.0379 (13)	0.0020 (10)	0.0117 (10)	0.0037 (10)
C11	0.0320 (11)	0.0324 (11)	0.0426 (13)	−0.0046 (9)	0.0107 (10)	−0.0066 (10)
C12	0.0337 (11)	0.0369 (12)	0.0320 (12)	−0.0043 (9)	0.0081 (9)	−0.0071 (10)
C13	0.0483 (14)	0.0429 (13)	0.0333 (13)	−0.0021 (11)	0.0144 (11)	−0.0018 (10)
C14	0.077 (2)	0.0639 (19)	0.0447 (17)	0.0044 (17)	0.0156 (15)	0.0145 (15)
O1W	0.0566 (12)	0.0612 (13)	0.0791 (16)	−0.0010 (10)	0.0234 (11)	0.0110 (12)

Cu1—O1	1.9477 (17)	C4—C5	1.392 (3)
Cu1—N3	1.989 (2)	C4—H4A	0.9300
Cu1—N1	1.9898 (18)	C5—C6	1.479 (3)
Cu1—N2	2.0317 (19)	C6—C7	1.379 (3)
Cu1—Cl1	2.5588 (7)	C7—C8	1.382 (4)
O1—C11	1.270 (3)	C7—H7A	0.9300
O2—C11	1.234 (3)	C8—C9	1.376 (4)
O3—C13	1.441 (3)	C8—H8A	0.9300
O3—H1O3	0.88 (4)	C9—C10	1.381 (4)
N1—C1	1.336 (3)	C9—H9A	0.9300
N1—C5	1.342 (3)	C10—H10A	0.9300
N2—C10	1.336 (3)	C11—C12	1.522 (3)
N2—C6	1.356 (3)	C12—C13	1.529 (3)
N3—C12	1.484 (3)	C12—H12A	0.9800
N3—H1N3	0.85 (3)	C13—C14	1.498 (4)
N3—H2N3	0.80 (3)	C13—H13A	0.9800
C1—C2	1.377 (4)	C14—H14A	0.9600
C1—H1A	0.9300	C14—H14B	0.9600
C2—C3	1.373 (4)	C14—H14C	0.9600
C2—H2A	0.9300	O1W—H1W1	0.7668
C3—C4	1.373 (4)	O1W—H2W1	0.8436
C3—H3A	0.9300
O1—Cu1—N3	84.58 (8)	C4—C5—C6	124.1 (2)
O1—Cu1—N1	90.79 (7)	N2—C6—C7	121.7 (2)
N3—Cu1—N1	169.53 (9)	N2—C6—C5	114.61 (19)
O1—Cu1—N2	161.51 (8)	C7—C6—C5	123.7 (2)
N3—Cu1—N2	100.98 (8)	C6—C7—C8	119.0 (2)
N1—Cu1—N2	80.67 (8)	C6—C7—H7A	120.5
O1—Cu1—Cl1	96.05 (6)	C8—C7—H7A	120.5
N3—Cu1—Cl1	93.51 (7)	C9—C8—C7	119.4 (2)
N1—Cu1—Cl1	96.32 (6)	C9—C8—H8A	120.3
N2—Cu1—Cl1	101.14 (5)	C7—C8—H8A	120.3
C11—O1—Cu1	114.81 (15)	C8—C9—C10	118.9 (2)
C13—O3—H1O3	105 (2)	C8—C9—H9A	120.5
C1—N1—C5	119.3 (2)	C10—C9—H9A	120.5
C1—N1—Cu1	124.71 (17)	N2—C10—C9	122.3 (2)
C5—N1—Cu1	116.00 (15)	N2—C10—H10A	118.9
C10—N2—C6	118.8 (2)	C9—C10—H10A	118.9
C10—N2—Cu1	127.17 (16)	O2—C11—O1	125.1 (2)
C6—N2—Cu1	114.03 (15)	O2—C11—C12	118.2 (2)
C12—N3—Cu1	107.76 (15)	O1—C11—C12	116.7 (2)
C12—N3—H1N3	110.7 (17)	N3—C12—C11	111.47 (19)
Cu1—N3—H1N3	110.6 (17)	N3—C12—C13	113.29 (19)
C12—N3—H2N3	115 (2)	C11—C12—C13	109.98 (19)
Cu1—N3—H2N3	110 (2)	N3—C12—H12A	107.3
H1N3—N3—H2N3	102 (3)	C11—C12—H12A	107.3
N1—C1—C2	121.9 (3)	C13—C12—H12A	107.3
N1—C1—H1A	119.0	O3—C13—C14	107.4 (2)
C2—C1—H1A	119.0	O3—C13—C12	109.4 (2)
C3—C2—C1	119.2 (3)	C14—C13—C12	113.2 (2)
C3—C2—H2A	120.4	O3—C13—H13A	108.9
C1—C2—H2A	120.4	C14—C13—H13A	108.9
C4—C3—C2	119.2 (2)	C12—C13—H13A	108.9
C4—C3—H3A	120.4	C13—C14—H14A	109.5
C2—C3—H3A	120.4	C13—C14—H14B	109.5
C3—C4—C5	119.1 (2)	H14A—C14—H14B	109.5
C3—C4—H4A	120.4	C13—C14—H14C	109.5
C5—C4—H4A	120.4	H14A—C14—H14C	109.5
N1—C5—C4	121.2 (2)	H14B—C14—H14C	109.5
N1—C5—C6	114.65 (19)	H1W1—O1W—H2W1	97.9
N3—Cu1—O1—C11	18.27 (17)	C1—N1—C5—C6	−179.8 (2)
N1—Cu1—O1—C11	−171.14 (17)	Cu1—N1—C5—C6	0.9 (2)
N2—Cu1—O1—C11	126.9 (2)	C3—C4—C5—N1	−1.0 (4)
Cl1—Cu1—O1—C11	−74.70 (16)	C3—C4—C5—C6	179.2 (2)
O1—Cu1—N1—C1	17.4 (2)	C10—N2—C6—C7	0.1 (3)
N3—Cu1—N1—C1	81.0 (5)	Cu1—N2—C6—C7	−177.65 (17)
N2—Cu1—N1—C1	−179.0 (2)	C10—N2—C6—C5	180.0 (2)
Cl1—Cu1—N1—C1	−78.73 (19)	Cu1—N2—C6—C5	2.2 (2)
O1—Cu1—N1—C5	−163.29 (16)	N1—C5—C6—N2	−2.0 (3)
N3—Cu1—N1—C5	−99.7 (5)	C4—C5—C6—N2	177.8 (2)
N2—Cu1—N1—C5	0.23 (15)	N1—C5—C6—C7	177.8 (2)
Cl1—Cu1—N1—C5	100.54 (15)	C4—C5—C6—C7	−2.4 (4)
O1—Cu1—N2—C10	−115.5 (3)	N2—C6—C7—C8	−0.3 (4)
N3—Cu1—N2—C10	−9.4 (2)	C5—C6—C7—C8	179.8 (2)
N1—Cu1—N2—C10	−178.9 (2)	C6—C7—C8—C9	0.0 (4)
Cl1—Cu1—N2—C10	86.41 (19)	C7—C8—C9—C10	0.6 (4)
O1—Cu1—N2—C6	62.1 (3)	C6—N2—C10—C9	0.5 (4)
N3—Cu1—N2—C6	168.12 (15)	Cu1—N2—C10—C9	177.91 (18)
N1—Cu1—N2—C6	−1.37 (15)	C8—C9—C10—N2	−0.8 (4)
Cl1—Cu1—N2—C6	−96.04 (15)	Cu1—O1—C11—O2	167.49 (19)
O1—Cu1—N3—C12	−18.87 (15)	Cu1—O1—C11—C12	−12.2 (3)
N1—Cu1—N3—C12	−83.0 (5)	Cu1—N3—C12—C11	17.4 (2)
N2—Cu1—N3—C12	178.96 (15)	Cu1—N3—C12—C13	142.08 (18)
Cl1—Cu1—N3—C12	76.88 (15)	O2—C11—C12—N3	176.1 (2)
C5—N1—C1—C2	0.5 (4)	O1—C11—C12—N3	−4.2 (3)
Cu1—N1—C1—C2	179.73 (19)	O2—C11—C12—C13	49.6 (3)
N1—C1—C2—C3	−0.6 (4)	O1—C11—C12—C13	−130.7 (2)
C1—C2—C3—C4	−0.1 (4)	N3—C12—C13—O3	−57.7 (3)
C2—C3—C4—C5	0.9 (4)	C11—C12—C13—O3	67.8 (3)
C1—N1—C5—C4	0.4 (3)	N3—C12—C13—C14	62.1 (3)
Cu1—N1—C5—C4	−178.95 (17)	C11—C12—C13—C14	−172.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3i	0.77	2.12	2.875 (3)	168
O1W—H2W1···Cl1ii	0.84	2.38	3.213 (2)	170
N3—H1N3···O2iii	0.85 (3)	2.20 (2)	2.978 (3)	152 (3)
N3—H2N3···O1W	0.80 (3)	2.26 (3)	3.051 (3)	167 (3)
O3—H1O3···Cl1iv	0.88 (4)	2.29 (4)	3.118 (2)	156 (3)
C3—H3A···O2v	0.93	2.55	3.219 (4)	130
C4—H4A···Cl1vi	0.93	2.67	3.555 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3i	0.77	2.12	2.875 (3)	168
O1W—H2W1⋯Cl1ii	0.84	2.38	3.213 (2)	170
N3—H1N3⋯O2iii	0.85 (3)	2.20 (2)	2.978 (3)	152 (3)
N3—H2N3⋯O1W	0.80 (3)	2.26 (3)	3.051 (3)	167 (3)
O3—H1O3⋯Cl1iv	0.88 (4)	2.29 (4)	3.118 (2)	156 (3)
C3—H3A⋯O2v	0.93	2.55	3.219 (4)	130
C4—H4A⋯Cl1vi	0.93	2.67	3.555 (2)	160

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