Aqua­(2,2′-bipyridine)maleatocopper(II) dihydrate

In the mol­ecule of the title compound, [Cu(C₁₀H₈N₂)(C₄H₂O₄)(H₂O)]·2H₂O, the Cu(II) atom has elongated tetra­gonal pyramidal geometry, coordinated by one water O atom, two N atoms of the 2,2′-bipyridine ligand and two O atoms of the two carboxyl­ate groups of the maleate dianion. The mol­ecules are linked through hydrogen-bonding and π–π stacking inter­actions, forming a two-dimensional supra­molecular structure.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.052
• wR factor = 0.123
• Data-to-parameter ratio = 14.6

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); 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.

Aquamaleato(2,2^'-bipyridine)copper(II) dihydrate

Crystal data

[Cu(C10H8N2)(C4H2O4)(H2O)].2H2O	F(000) = 796
Mr = 387.83	Dx = 1.661 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3123 reflections
a = 8.9793 (18) Å	θ = 2.6–27.8°
b = 22.487 (5) Å	µ = 1.45 mm^−1
c = 7.7187 (15) Å	T = 292 K
β = 95.62 (3)°	Block, blue
V = 1551.0 (5) Å^3	0.20 × 0.06 × 0.06 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3528 independent reflections
Radiation source: fine-focus sealed tube	2257 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.760, Tmax = 0.918	k = −28→24
10456 measured reflections	l = −9→6

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
3528 reflections	(Δ/σ)max = 0.001
241 parameters	Δρmax = 0.42 e Å^−3
6 restraints	Δρmin = −0.36 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.08386 (5)	0.60739 (2)	0.63719 (6)	0.02924 (17)
O1	0.2542 (3)	0.62204 (12)	0.5087 (4)	0.0431 (8)
O2	0.4522 (3)	0.67026 (13)	0.4346 (4)	0.0435 (8)
O3	−0.0163 (3)	0.67980 (12)	0.5575 (4)	0.0407 (7)
O4	−0.0346 (3)	0.77636 (13)	0.5061 (4)	0.0455 (8)
O5	0.1509 (4)	0.63151 (14)	0.9184 (4)	0.0354 (7)
H5a	0.235 (4)	0.637 (2)	0.959 (6)	0.050 (15)*
H5b	0.102 (4)	0.6584 (18)	0.950 (5)	0.043 (15)*
O6	0.6422 (5)	0.7250 (2)	−0.0366 (6)	0.0673 (12)
H6a	0.723 (5)	0.725 (3)	0.000 (8)	0.10 (3)*
H6b	0.606 (6)	0.7568 (19)	−0.054 (7)	0.08 (2)*
O7	0.4389 (4)	0.64095 (17)	0.0742 (6)	0.0473 (9)
H7a	0.451 (5)	0.646 (2)	0.181 (5)	0.053 (17)*
H7b	0.497 (5)	0.661 (2)	0.043 (6)	0.043 (17)*
N1	−0.1045 (3)	0.57454 (15)	0.7188 (4)	0.0312 (8)
N2	0.1452 (3)	0.52221 (14)	0.6714 (4)	0.0269 (7)
C1	−0.2298 (4)	0.6060 (2)	0.7369 (6)	0.0407 (11)
H1	−0.2329	0.6462	0.7085	0.049*
C2	−0.3532 (4)	0.5797 (2)	0.7966 (6)	0.0500 (13)
H2	−0.4393	0.6018	0.8071	0.060*
C3	−0.3484 (5)	0.5206 (2)	0.8406 (6)	0.0508 (13)
H3	−0.4307	0.5023	0.8823	0.061*
C4	−0.2196 (5)	0.4885 (2)	0.8223 (5)	0.0429 (11)
H4	−0.2147	0.4483	0.8502	0.051*
C5	−0.0990 (4)	0.51663 (18)	0.7623 (5)	0.0302 (9)
C6	0.0423 (4)	0.48682 (18)	0.7357 (5)	0.0297 (9)
C7	0.0717 (5)	0.42719 (19)	0.7704 (5)	0.0407 (11)
H7	0.0005	0.4033	0.8157	0.049*
C8	0.2087 (5)	0.4037 (2)	0.7368 (6)	0.0480 (12)
H8	0.2302	0.3638	0.7587	0.058*
C9	0.3121 (5)	0.4400 (2)	0.6708 (6)	0.0453 (12)
H9	0.4049	0.4252	0.6478	0.054*
C10	0.2763 (4)	0.49848 (19)	0.6394 (5)	0.0375 (10)
H10	0.3465	0.5228	0.5936	0.045*
C11	0.3419 (4)	0.66653 (18)	0.5198 (5)	0.0312 (9)
C12	0.3159 (4)	0.71698 (17)	0.6396 (5)	0.0304 (9)
H12	0.3995	0.7306	0.7091	0.037*
C13	0.1889 (4)	0.74438 (17)	0.6585 (5)	0.0294 (9)
H13	0.1941	0.7752	0.7391	0.035*
C14	0.0363 (4)	0.73227 (18)	0.5665 (5)	0.0314 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0301 (3)	0.0223 (3)	0.0358 (3)	−0.0035 (2)	0.0056 (2)	0.0006 (2)
O1	0.0499 (18)	0.0297 (18)	0.053 (2)	−0.0103 (13)	0.0236 (15)	−0.0069 (14)
O2	0.0315 (15)	0.046 (2)	0.056 (2)	−0.0033 (13)	0.0152 (14)	0.0012 (15)
O3	0.0393 (16)	0.0251 (17)	0.055 (2)	−0.0079 (13)	−0.0075 (14)	0.0061 (14)
O4	0.0351 (15)	0.0292 (17)	0.071 (2)	0.0022 (13)	0.0015 (15)	0.0161 (15)
O5	0.0380 (18)	0.0312 (18)	0.0367 (18)	−0.0018 (15)	0.0017 (15)	−0.0043 (14)
O6	0.041 (2)	0.052 (3)	0.109 (4)	0.003 (2)	0.009 (2)	0.000 (2)
O7	0.0375 (19)	0.053 (2)	0.051 (3)	0.0041 (17)	0.0032 (18)	−0.0050 (19)
N1	0.0278 (17)	0.032 (2)	0.034 (2)	−0.0037 (14)	0.0026 (15)	−0.0038 (15)
N2	0.0302 (16)	0.0234 (18)	0.0272 (18)	−0.0019 (14)	0.0027 (14)	−0.0003 (14)
C1	0.035 (2)	0.044 (3)	0.043 (3)	0.004 (2)	0.007 (2)	−0.009 (2)
C2	0.025 (2)	0.076 (4)	0.050 (3)	0.004 (2)	0.011 (2)	−0.012 (3)
C3	0.039 (3)	0.077 (4)	0.040 (3)	−0.016 (3)	0.016 (2)	0.003 (3)
C4	0.045 (3)	0.046 (3)	0.039 (3)	−0.015 (2)	0.008 (2)	0.003 (2)
C5	0.037 (2)	0.029 (2)	0.025 (2)	−0.0082 (18)	0.0021 (17)	−0.0002 (17)
C6	0.034 (2)	0.027 (2)	0.026 (2)	−0.0042 (17)	−0.0029 (17)	−0.0023 (17)
C7	0.052 (3)	0.028 (3)	0.041 (3)	−0.006 (2)	−0.003 (2)	0.0048 (19)
C8	0.059 (3)	0.033 (3)	0.049 (3)	0.013 (2)	−0.010 (2)	0.000 (2)
C9	0.039 (2)	0.045 (3)	0.051 (3)	0.016 (2)	−0.002 (2)	−0.002 (2)
C10	0.035 (2)	0.040 (3)	0.037 (2)	0.0006 (19)	0.0006 (19)	−0.003 (2)
C11	0.029 (2)	0.030 (2)	0.034 (2)	−0.0015 (17)	−0.0018 (18)	0.0075 (18)
C12	0.035 (2)	0.029 (2)	0.026 (2)	−0.0064 (17)	−0.0003 (18)	0.0055 (17)
C13	0.036 (2)	0.024 (2)	0.028 (2)	−0.0058 (17)	0.0023 (18)	−0.0007 (17)
C14	0.032 (2)	0.031 (2)	0.033 (2)	0.0005 (18)	0.0083 (18)	0.0004 (19)

Geometric parameters (Å, º)

Cu1—O1	1.931 (3)	C10—C9	1.369 (6)
Cu1—O3	1.931 (3)	C10—H10	0.9300
Cu1—O5	2.261 (3)	C11—C12	1.497 (6)
Cu1—N1	2.003 (3)	C12—C13	1.317 (5)
Cu1—N2	2.003 (3)	C12—H12	0.9300
O3—C14	1.270 (4)	C7—C8	1.386 (6)
O5—H5a	0.80 (3)	C7—H7	0.9300
O5—H5b	0.80 (3)	C9—C8	1.372 (6)
O1—C11	1.271 (4)	C9—H9	0.9300
N2—C10	1.338 (5)	C8—H8	0.9300
N2—C6	1.350 (5)	C13—H13	0.9300
O4—C14	1.244 (5)	C4—C3	1.382 (6)
O2—C11	1.244 (4)	C4—H4	0.9300
N1—C5	1.345 (5)	C2—C3	1.371 (7)
N1—C1	1.348 (5)	C2—H2	0.9300
C6—C7	1.388 (5)	C3—H3	0.9300
C6—C5	1.467 (5)	O7—H7b	0.75 (3)
C5—C4	1.373 (5)	O7—H7a	0.83 (4)
C14—C13	1.505 (5)	O6—H6a	0.75 (4)
C1—C2	1.374 (6)	O6—H6b	0.79 (4)
C1—H1	0.9300
O1—Cu1—O3	93.44 (12)	N2—C10—C9	123.1 (4)
O1—Cu1—N1	163.76 (13)	N2—C10—H10	118.5
O3—Cu1—N1	91.72 (12)	C9—C10—H10	118.5
O1—Cu1—N2	90.55 (12)	O2—C11—O1	122.5 (4)
O3—Cu1—N2	164.04 (12)	O2—C11—C12	117.1 (4)
N1—Cu1—N2	80.53 (13)	O1—C11—C12	120.4 (4)
O1—Cu1—O5	107.62 (12)	C13—C12—C11	127.7 (4)
O3—Cu1—O5	100.11 (12)	C13—C12—H12	116.1
N1—Cu1—O5	86.57 (12)	C11—C12—H12	116.1
N2—Cu1—O5	93.38 (12)	C8—C7—C6	119.2 (4)
C14—O3—Cu1	127.3 (3)	C8—C7—H7	120.4
Cu1—O5—H5a	125 (3)	C6—C7—H7	120.4
Cu1—O5—H5b	112 (3)	C10—C9—C8	118.8 (4)
H5a—O5—H5b	106 (4)	C10—C9—H9	120.6
C11—O1—Cu1	128.1 (3)	C8—C9—H9	120.6
C10—N2—C6	118.6 (4)	C9—C8—C7	119.2 (4)
C10—N2—Cu1	126.3 (3)	C9—C8—H8	120.4
C6—N2—Cu1	115.0 (3)	C7—C8—H8	120.4
C5—N1—C1	119.5 (4)	C12—C13—C14	128.4 (4)
C5—N1—Cu1	115.1 (3)	C12—C13—H13	115.8
C1—N1—Cu1	125.4 (3)	C14—C13—H13	115.8
N2—C6—C7	121.1 (4)	C5—C4—C3	119.3 (4)
N2—C6—C5	114.5 (3)	C5—C4—H4	120.3
C7—C6—C5	124.4 (4)	C3—C4—H4	120.3
N1—C5—C4	121.3 (4)	C3—C2—C1	119.6 (4)
N1—C5—C6	114.7 (3)	C3—C2—H2	120.2
C4—C5—C6	123.9 (4)	C1—C2—H2	120.2
O4—C14—O3	123.1 (4)	C2—C3—C4	119.1 (4)
O4—C14—C13	116.2 (4)	C2—C3—H3	120.5
O3—C14—C13	120.7 (3)	C4—C3—H3	120.5
N1—C1—C2	121.2 (4)	H7b—O7—H7a	102 (5)
N1—C1—H1	119.4	H6a—O6—H6b	116 (6)
C2—C1—H1	119.4
O1—Cu1—O3—C14	−53.2 (3)	C1—N1—C5—C6	179.5 (3)
N1—Cu1—O3—C14	142.2 (3)	Cu1—N1—C5—C6	−2.4 (4)
N2—Cu1—O3—C14	−157.4 (4)	N2—C6—C5—N1	0.0 (5)
O5—Cu1—O3—C14	55.4 (3)	C7—C6—C5—N1	−179.4 (4)
O3—Cu1—O1—C11	58.3 (3)	N2—C6—C5—C4	178.3 (4)
N1—Cu1—O1—C11	166.6 (4)	C7—C6—C5—C4	−1.1 (6)
N2—Cu1—O1—C11	−137.2 (3)	Cu1—O3—C14—O4	177.4 (3)
O5—Cu1—O1—C11	−43.4 (4)	Cu1—O3—C14—C13	−4.7 (5)
O1—Cu1—N2—C10	11.8 (3)	C5—N1—C1—C2	−1.0 (6)
O3—Cu1—N2—C10	116.4 (5)	Cu1—N1—C1—C2	−179.0 (3)
N1—Cu1—N2—C10	178.2 (3)	C6—N2—C10—C9	−0.9 (6)
O5—Cu1—N2—C10	−95.9 (3)	Cu1—N2—C10—C9	178.0 (3)
O1—Cu1—N2—C6	−169.2 (3)	Cu1—O1—C11—O2	177.2 (3)
O3—Cu1—N2—C6	−64.7 (5)	Cu1—O1—C11—C12	−2.2 (5)
N1—Cu1—N2—C6	−2.9 (2)	O2—C11—C12—C13	134.2 (4)
O5—Cu1—N2—C6	83.1 (3)	O1—C11—C12—C13	−46.3 (6)
O1—Cu1—N1—C5	60.3 (6)	N2—C6—C7—C8	−0.6 (6)
O3—Cu1—N1—C5	168.8 (3)	C5—C6—C7—C8	178.7 (4)
N2—Cu1—N1—C5	2.9 (3)	N2—C10—C9—C8	0.6 (6)
O5—Cu1—N1—C5	−91.1 (3)	C10—C9—C8—C7	−0.3 (7)
O1—Cu1—N1—C1	−121.7 (5)	C6—C7—C8—C9	0.3 (6)
O3—Cu1—N1—C1	−13.1 (3)	C11—C12—C13—C14	0.5 (7)
N2—Cu1—N1—C1	−179.1 (3)	O4—C14—C13—C12	−132.4 (4)
O5—Cu1—N1—C1	86.9 (3)	O3—C14—C13—C12	49.6 (6)
C10—N2—C6—C7	0.8 (5)	N1—C5—C4—C3	−1.0 (6)
Cu1—N2—C6—C7	−178.2 (3)	C6—C5—C4—C3	−179.2 (4)
C10—N2—C6—C5	−178.6 (3)	N1—C1—C2—C3	0.8 (7)
Cu1—N2—C6—C5	2.4 (4)	C1—C2—C3—C4	−0.6 (7)
C1—N1—C5—C4	1.1 (6)	C5—C4—C3—C2	0.7 (7)
Cu1—N1—C5—C4	179.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5a···O7^i	0.80 (3)	1.96 (3)	2.752 (5)	172 (5)
O7—H7b···O6	0.75 (3)	2.07 (4)	2.819 (6)	174 (5)
O6—H6a···O4^ii	0.75 (4)	2.18 (4)	2.889 (5)	159 (7)
O7—H7a···O2	0.83 (4)	2.03 (4)	2.850 (5)	169 (5)
O5—H5b···O4^iii	0.80 (3)	1.99 (3)	2.783 (4)	174 (4)
O6—H6b···O2^iv	0.79 (4)	2.14 (4)	2.903 (5)	162 (6)

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