catena-Poly[[[aqua­bis(acetato-κO)­copper(II)]-μ-1,3-di-4-pyridylpropane-κ2N:N′] monohydrate]

Du, Z.-X.; Li, J.-X.

doi:10.1107/S160053680703334X

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catena-Poly[[[aquabis(acetato-κO)copper(II)]-μ-1,3-di-4-pyridylpropane-κ²N:N′] monohydrate]

Z.-X. Du and J.-X. Li

In the title complex, {[Cu(CH₃COO)₂(C₁₃H₁₄N₂)(H₂O)]·H₂O}_n, the Cu atom is five-coordinated in a distorted square-pyramidal geometry by one O atom of the coordinated water molecule, two O atoms from two acetate anions and two N atoms from two 1,3-di-4-pyridylpropane (dpp) ligands. The dpp ligands bridge the Cu atoms to form a zigzag chain. The crystal structure involves O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703334X/kp2117sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680703334X/kp2117Isup2.hkl Contains datablock I

CCDC reference: 657574

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.009 Å
R factor = 0.047
wR factor = 0.117
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit     F 2 2d
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O3  -CU1 -O1  -C14   156.80  1.30   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            O1  -CU1 -O3  -C16    12.00  1.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            N2  -CU1 -N1  -C5   -116.20  1.30  16.644   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            N2  -CU1 -N1  -C1     61.10  1.50  16.644   1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.50
           From the CIF: _reflns_number_total               3599
           Count of symmetry unique reflns         1924
           Completeness (_total/calc)            187.06%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1675
           Fraction of Friedel pairs measured     0.871
           Are heavy atom types Z>Si present        yes
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.05
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The ligand 1,3-di-4-pyridylpropane (dpp) has been extensively studied in recent years due to its strong coordination capability and bridging function. Here we report the structure of a new coordination polymer (I) (Fig. 1). The polymeric chain is assembled of [Cu(C₁₃H₁₄N₂)(CH₃COO)₂(H₂O)].H₂O with the five coordinated Cu^II. The coordination sphere includes the coordinated water molecule, two carboxyl O atoms from two acetate anions and two pyridyl N from two 1,3-di-4-pyridylpropane(dpp) ligands (Table 1). The plane N1/O3/N2A/O1 defines the base of the pyramid while water O5 is the apex. The distance from Cu to the least-squares plane N1/O3/N2A/O1 is 0.1272 (3) Å. The dpp ligand acts as a bridging ligand linking neighbouring Cu^II atoms into a zigzag chain with the Cu1···Cu1 (-x + 7/4, y - 1/4, z - 3/4) separation distance of 12.851 (2) Å.

In the crystal structure of (I), there is π-π stacking interactions between the adjacent pyridine rings of neighbouring chains. The dihedral angle of aromatics involved in stacking is 8.788 (1) °. Interplanar average distance and ring-centroid separation distance are 3.441 (1) Å and 3.701 (4) Å, respectively. The chain structure is crosswise arranged into two-dimensional network (Fig. 2) by π-π stacking. The coordinated and uncoordinate water molecules, and carboxyl group take part in intermolecular hydrogen bonding (Table 2) stabilizing the structure.

Related literature top

None of these references are cited in the CIF; do you wish to add them all here?

For related literature, see: Carlucci et al. (2002); Dai et al. (2004); Hou et al. (2003); Konar et al. (2004); Lee et al. (2004); Li et al. (2004, 2005); Madalan et al. (2005); Manna et al. (2005); Nassimbeni et al. (2004); Niu et al. (2003); Rarig & Zubieta (2003); Sunahara et al. (2004); Tong et al. (2002); Xia et al. (2004).

Experimental top

The ligand dpp (1 mmol, 0.2 g) was dissolved in a mixture water - methanol (v/v 1:1, 20 ml). To this solution, Cu(CH₃COO)₂. 4H₂O (1 mmol, 0.26 g) was added and the resulting mixture was stirred and refluxed at 353 K for 3 h. Then the reaction mixture was cooled to room temperature. After filtration and evaporation in air for five days, dark-blue block-shaped crystals were obtained in the yield of 45%.

Structure description top

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Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. A segment of the polymeric structure of (I) with the atom numbering scheme. H atoms and solvent molecules have been omitted for clarity. Labelling A corresponds to symmetry operation -x + 7/4, y - 1/4, z - 3/4.
	Fig. 2. Packing of (I) showing the intercrossed chains in the bc plane stabilized by π-π stacking and hydrogen bonds. H atoms bonded to C have been omitted for clarity.

catena-Poly[[[aquabis(acetato-κO)copper(II)]-µ-1,3-di-4-pyridylpropane-\ κ²N:N'] monohydrate] top

Crystal data top

[Cu(C₂H₃O₂)₂(C₁₃H₁₄N₂)(H₂O)]·H₂O	F(000) = 3472
M_r = 415.92	D_x = 1.401 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 2d	Cell parameters from 1579 reflections
a = 18.988 (3) Å	θ = 2.5–17.4°
b = 32.249 (6) Å	µ = 1.14 mm⁻¹
c = 12.883 (2) Å	T = 291 K
V = 7889 (2) Å³	Block, blue
Z = 16	0.26 × 0.18 × 0.10 mm

Data collection top

Bruker APEX II CCD area-detector diffractometer	3599 independent reflections
Radiation source: fine-focus sealed tube	2517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
φ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→21
T_min = 0.757, T_max = 0.895	k = −38→38
11662 measured reflections	l = −15→15

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.0455P)² + 4.4493P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.118	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.37 e Å⁻³
3599 reflections	Δρ_min = −0.34 e Å⁻³
238 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00018 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1675 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.03 (2)

Crystal data top

[Cu(C₂H₃O₂)₂(C₁₃H₁₄N₂)(H₂O)]·H₂O	V = 7889 (2) Å³
M_r = 415.92	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 18.988 (3) Å	µ = 1.14 mm⁻¹
b = 32.249 (6) Å	T = 291 K
c = 12.883 (2) Å	0.26 × 0.18 × 0.10 mm

Data collection top

Bruker APEX II CCD area-detector diffractometer	3599 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2517 reflections with I > 2σ(I)
T_min = 0.757, T_max = 0.895	R_int = 0.062
11662 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.118	Δρ_max = 0.37 e Å⁻³
S = 1.03	Δρ_min = −0.34 e Å⁻³
3599 reflections	Absolute structure: Flack (1983), 1675 Friedel pairs
238 parameters	Absolute structure parameter: −0.03 (2)
1 restraint

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	0.94362 (3)	0.221410 (19)	0.13402 (4)	0.0506 (2)
O1	1.0258 (2)	0.21314 (13)	0.2238 (3)	0.0634 (11)
O2	1.0911 (3)	0.26709 (19)	0.1777 (4)	0.0951 (17)
O3	0.8590 (2)	0.22242 (12)	0.0479 (3)	0.0566 (10)
O4	0.8358 (2)	0.16359 (14)	0.1289 (5)	0.0794 (12)
N1	0.8914 (2)	0.25056 (13)	0.2485 (3)	0.0468 (11)
N2	0.7602 (2)	0.43467 (13)	0.7749 (3)	0.0487 (11)
C1	0.8983 (3)	0.24184 (17)	0.3503 (4)	0.0498 (14)
H1	0.9299	0.2213	0.3697	0.060*
C2	0.8608 (3)	0.26183 (17)	0.4273 (4)	0.0499 (14)
H2	0.8683	0.2549	0.4965	0.060*
C3	0.8124 (3)	0.29185 (14)	0.4024 (4)	0.0434 (13)
C4	0.8042 (3)	0.30058 (19)	0.2972 (5)	0.0552 (15)
H4	0.7718	0.3205	0.2758	0.066*
C5	0.8443 (3)	0.27966 (17)	0.2248 (4)	0.0551 (15)
H5A	0.8380	0.2863	0.1552	0.066*
C6	0.7696 (3)	0.31317 (18)	0.4853 (4)	0.0553 (15)
H6A	0.7473	0.2919	0.5272	0.066*
H6B	0.8020	0.3281	0.5302	0.066*
C7	0.7137 (3)	0.34300 (18)	0.4510 (5)	0.0579 (16)
H7A	0.6850	0.3299	0.3980	0.069*
H7B	0.7360	0.3671	0.4201	0.069*
C8	0.6663 (3)	0.35713 (19)	0.5390 (5)	0.0657 (17)
H8A	0.6275	0.3729	0.5096	0.079*
H8B	0.6464	0.3328	0.5721	0.079*
C9	0.7015 (3)	0.38344 (15)	0.6215 (5)	0.0503 (14)
C10	0.7441 (3)	0.41616 (17)	0.5972 (4)	0.0529 (15)
H10	0.7545	0.4217	0.5281	0.064*
C11	0.7718 (3)	0.44097 (17)	0.6741 (4)	0.0517 (15)
H11	0.8000	0.4632	0.6547	0.062*
C12	0.7200 (4)	0.40184 (17)	0.7989 (5)	0.0627 (16)
H12	0.7115	0.3965	0.8687	0.075*
C13	0.6905 (3)	0.37572 (18)	0.7271 (5)	0.0607 (16)
H13	0.6636	0.3532	0.7483	0.073*
C14	1.0826 (4)	0.2345 (3)	0.2237 (5)	0.0641 (17)
C15	1.1433 (4)	0.2170 (3)	0.2868 (7)	0.101 (3)
H15A	1.1846	0.2336	0.2759	0.152*
H15B	1.1525	0.1890	0.2652	0.152*
H15C	1.1311	0.2172	0.3591	0.152*
C16	0.8226 (3)	0.1898 (2)	0.0627 (5)	0.0638 (17)
C17	0.7590 (4)	0.1858 (3)	−0.0080 (6)	0.094 (2)
H17A	0.7302	0.1631	0.0149	0.141*
H17B	0.7745	0.1807	−0.0778	0.141*
H17C	0.7322	0.2110	−0.0059	0.141*
O5	0.9779 (3)	0.28664 (15)	0.0658 (4)	0.0954 (16)
H1W	1.0175	0.2760	0.0731	0.143*
H2W	0.9795	0.3068	0.0257	0.143*
O6	0.7594 (3)	0.09240 (19)	0.1507 (5)	0.133 (2)
H3W	0.7813	0.1140	0.1647	0.200*
H4W	0.7643	0.0762	0.0993	0.200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0534 (4)	0.0558 (4)	0.0425 (3)	0.0047 (3)	−0.0012 (4)	−0.0031 (3)
O1	0.063 (3)	0.074 (3)	0.052 (3)	0.013 (2)	−0.007 (2)	0.002 (2)
O2	0.088 (4)	0.113 (4)	0.084 (4)	−0.015 (3)	−0.006 (3)	0.018 (3)
O3	0.056 (3)	0.062 (3)	0.052 (2)	0.006 (2)	−0.007 (2)	−0.0083 (19)
O4	0.077 (3)	0.077 (3)	0.085 (3)	−0.011 (2)	−0.008 (3)	0.002 (3)
N1	0.049 (3)	0.046 (3)	0.045 (3)	0.003 (2)	0.000 (2)	0.001 (2)
N2	0.057 (3)	0.047 (3)	0.042 (3)	−0.004 (2)	0.003 (2)	0.004 (2)
C1	0.047 (3)	0.052 (3)	0.051 (4)	0.004 (3)	−0.003 (3)	0.005 (3)
C2	0.051 (4)	0.053 (3)	0.046 (3)	−0.001 (3)	−0.004 (3)	0.002 (3)
C3	0.044 (3)	0.037 (2)	0.049 (4)	−0.007 (2)	−0.005 (3)	−0.008 (2)
C4	0.067 (4)	0.052 (3)	0.046 (3)	0.013 (3)	−0.009 (3)	−0.003 (3)
C5	0.070 (4)	0.056 (3)	0.039 (3)	0.014 (3)	−0.006 (3)	0.000 (3)
C6	0.055 (4)	0.057 (3)	0.054 (4)	−0.007 (3)	−0.002 (3)	−0.013 (3)
C7	0.062 (4)	0.053 (3)	0.059 (4)	0.010 (3)	−0.008 (3)	−0.018 (3)
C8	0.053 (4)	0.069 (4)	0.075 (4)	0.007 (3)	−0.002 (3)	−0.023 (3)
C9	0.044 (3)	0.041 (3)	0.066 (4)	0.003 (2)	−0.002 (3)	−0.012 (3)
C10	0.056 (4)	0.057 (3)	0.046 (3)	0.004 (3)	0.002 (3)	−0.009 (3)
C11	0.054 (4)	0.050 (3)	0.051 (4)	−0.005 (3)	−0.002 (3)	0.000 (3)
C12	0.086 (5)	0.052 (3)	0.050 (3)	−0.007 (3)	0.000 (3)	0.007 (3)
C13	0.070 (4)	0.049 (3)	0.064 (4)	−0.016 (3)	0.000 (3)	0.003 (3)
C14	0.048 (4)	0.099 (5)	0.046 (4)	0.004 (4)	0.007 (3)	−0.014 (4)
C15	0.058 (5)	0.150 (8)	0.095 (6)	0.016 (5)	−0.026 (5)	−0.007 (5)
C16	0.055 (4)	0.079 (5)	0.057 (4)	0.009 (4)	0.001 (3)	−0.026 (4)
C17	0.063 (5)	0.135 (7)	0.084 (5)	0.003 (5)	−0.013 (4)	−0.050 (5)
O5	0.079 (3)	0.094 (4)	0.113 (4)	−0.001 (3)	0.011 (3)	0.027 (3)
O6	0.169 (6)	0.124 (5)	0.107 (5)	−0.062 (4)	0.025 (5)	−0.015 (4)

Geometric parameters (Å, º) top

Cu1—O3	1.952 (4)	C7—C8	1.517 (8)
Cu1—O1	1.960 (4)	C7—H7A	0.9700
Cu1—N1	2.011 (4)	C7—H7B	0.9700
Cu1—N2ⁱ	2.037 (4)	C8—C9	1.516 (8)
Cu1—O5	2.371 (5)	C8—H8A	0.9700
O1—C14	1.280 (8)	C8—H8B	0.9700
O2—C14	1.217 (8)	C9—C10	1.366 (7)
O3—C16	1.275 (8)	C9—C13	1.398 (8)
O4—C16	1.226 (8)	C10—C11	1.377 (7)
N1—C5	1.332 (6)	C10—H10	0.9300
N1—C1	1.347 (6)	C11—H11	0.9300
N2—C11	1.332 (6)	C12—C13	1.370 (8)
N2—C12	1.342 (7)	C12—H12	0.9300
N2—Cu1ⁱⁱ	2.037 (4)	C13—H13	0.9300
C1—C2	1.381 (7)	C14—C15	1.520 (9)
C1—H1	0.9300	C15—H15A	0.9600
C2—C3	1.373 (7)	C15—H15B	0.9600
C2—H2	0.9300	C15—H15C	0.9600
C3—C4	1.393 (8)	C16—C17	1.517 (9)
C3—C6	1.508 (7)	C17—H17A	0.9600
C4—C5	1.380 (8)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600
C5—H5A	0.9300	O5—H1W	0.8307
C6—C7	1.500 (8)	O5—H2W	0.8299
C6—H6A	0.9700	O6—H3W	0.8316
C6—H6B	0.9700	O6—H4W	0.8492

O3—Cu1—O1	172.88 (18)	H7A—C7—H7B	107.8
O3—Cu1—N1	90.19 (17)	C9—C8—C7	115.5 (5)
O1—Cu1—N1	91.35 (17)	C9—C8—H8A	108.4
O3—Cu1—N2ⁱ	88.36 (17)	C7—C8—H8A	108.4
O1—Cu1—N2ⁱ	89.17 (17)	C9—C8—H8B	108.4
N1—Cu1—N2ⁱ	172.12 (18)	C7—C8—H8B	108.4
O3—Cu1—O5	90.03 (17)	H8A—C8—H8B	107.5
O1—Cu1—O5	96.93 (19)	C10—C9—C13	116.7 (5)
N1—Cu1—O5	89.59 (17)	C10—C9—C8	122.2 (6)
N2ⁱ—Cu1—O5	98.15 (18)	C13—C9—C8	121.1 (5)
C14—O1—Cu1	126.6 (4)	C9—C10—C11	120.7 (5)
C16—O3—Cu1	110.4 (4)	C9—C10—H10	119.7
C5—N1—C1	115.8 (5)	C11—C10—H10	119.7
C5—N1—Cu1	119.5 (4)	N2—C11—C10	123.3 (5)
C1—N1—Cu1	124.6 (4)	N2—C11—H11	118.4
C11—N2—C12	116.1 (5)	C10—C11—H11	118.4
C11—N2—Cu1ⁱⁱ	120.8 (4)	N2—C12—C13	124.2 (6)
C12—N2—Cu1ⁱⁱ	123.0 (4)	N2—C12—H12	117.9
N1—C1—C2	123.5 (5)	C13—C12—H12	117.9
N1—C1—H1	118.3	C12—C13—C9	119.1 (5)
C2—C1—H1	118.3	C12—C13—H13	120.5
C3—C2—C1	120.4 (5)	C9—C13—H13	120.5
C3—C2—H2	119.8	O2—C14—O1	125.3 (7)
C1—C2—H2	119.8	O2—C14—C15	118.8 (7)
C2—C3—C4	116.4 (5)	O1—C14—C15	115.9 (7)
C2—C3—C6	121.1 (5)	C14—C15—H15A	109.5
C4—C3—C6	122.5 (5)	C14—C15—H15B	109.5
C5—C4—C3	119.8 (5)	H15A—C15—H15B	109.5
C5—C4—H4	120.1	C14—C15—H15C	109.5
C3—C4—H4	120.1	H15A—C15—H15C	109.5
N1—C5—C4	124.0 (5)	H15B—C15—H15C	109.5
N1—C5—H5A	118.0	O4—C16—O3	124.2 (6)
C4—C5—H5A	118.0	O4—C16—C17	121.5 (7)
C7—C6—C3	117.7 (5)	O3—C16—C17	114.4 (7)
C7—C6—H6A	107.9	C16—C17—H17A	109.5
C3—C6—H6A	107.9	C16—C17—H17B	109.5
C7—C6—H6B	107.9	H17A—C17—H17B	109.5
C3—C6—H6B	107.9	C16—C17—H17C	109.5
H6A—C6—H6B	107.2	H17A—C17—H17C	109.5
C6—C7—C8	113.1 (5)	H17B—C17—H17C	109.5
C6—C7—H7A	109.0	Cu1—O5—H1W	80.8
C8—C7—H7A	109.0	Cu1—O5—H2W	159.1
C6—C7—H7B	109.0	H1W—O5—H2W	111.2
C8—C7—H7B	109.0	H3W—O6—H4W	129.1

O3—Cu1—O1—C14	156.8 (13)	C1—N1—C5—C4	0.4 (8)
N1—Cu1—O1—C14	−100.8 (5)	Cu1—N1—C5—C4	178.0 (5)
N2ⁱ—Cu1—O1—C14	87.1 (5)	C3—C4—C5—N1	0.5 (9)
O5—Cu1—O1—C14	−11.0 (5)	C2—C3—C6—C7	−174.9 (5)
O1—Cu1—O3—C16	12.0 (17)	C4—C3—C6—C7	3.6 (8)
N1—Cu1—O3—C16	−90.4 (4)	C3—C6—C7—C8	170.5 (5)
N2ⁱ—Cu1—O3—C16	81.8 (4)	C6—C7—C8—C9	66.6 (7)
O5—Cu1—O3—C16	180.0 (4)	C7—C8—C9—C10	47.2 (8)
O3—Cu1—N1—C5	−36.9 (4)	C7—C8—C9—C13	−134.2 (6)
O1—Cu1—N1—C5	150.1 (4)	C13—C9—C10—C11	−2.7 (8)
N2ⁱ—Cu1—N1—C5	−116.2 (13)	C8—C9—C10—C11	175.9 (5)
O5—Cu1—N1—C5	53.1 (4)	C12—N2—C11—C10	0.9 (9)
O3—Cu1—N1—C1	140.5 (4)	Cu1ⁱⁱ—N2—C11—C10	177.5 (4)
O1—Cu1—N1—C1	−32.6 (4)	C9—C10—C11—N2	0.9 (9)
N2ⁱ—Cu1—N1—C1	61.1 (15)	C11—N2—C12—C13	−0.8 (9)
O5—Cu1—N1—C1	−129.5 (4)	Cu1ⁱⁱ—N2—C12—C13	−177.4 (5)
C5—N1—C1—C2	−1.3 (8)	N2—C12—C13—C9	−0.9 (10)
Cu1—N1—C1—C2	−178.8 (4)	C10—C9—C13—C12	2.7 (8)
N1—C1—C2—C3	1.3 (9)	C8—C9—C13—C12	−176.0 (6)
C1—C2—C3—C4	−0.2 (8)	Cu1—O1—C14—O2	10.7 (9)
C1—C2—C3—C6	178.4 (5)	Cu1—O1—C14—C15	−169.1 (4)
C2—C3—C4—C5	−0.6 (8)	Cu1—O3—C16—O4	6.4 (7)
C6—C3—C4—C5	−179.2 (5)	Cu1—O3—C16—C17	−174.7 (4)

Symmetry codes: (i) −x+7/4, y−1/4, z−3/4; (ii) −x+7/4, y+1/4, z+3/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···O2	0.83	1.96	2.663 (8)	142
O5—H2W···O6ⁱⁱⁱ	0.83	1.99	2.795 (8)	164
O6—H3W···O4	0.83	1.96	2.730 (7)	154
O6—H4W···O1^iv	0.85	2.07	2.916 (7)	180

Symmetry codes: (iii) −x+7/4, y+1/4, z−1/4; (iv) x−1/4, −y+1/4, z−1/4.

Experimental details

Crystal data
Chemical formula	[Cu(C₂H₃O₂)₂(C₁₃H₁₄N₂)(H₂O)]·H₂O
M_r	415.92
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	291
a, b, c (Å)	18.988 (3), 32.249 (6), 12.883 (2)
V (Å³)	7889 (2)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.26 × 0.18 × 0.10

Data collection
Diffractometer	Bruker APEX II CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.757, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	11662, 3599, 2517
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.118, 1.03
No. of reflections	3599
No. of parameters	238
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.34
Absolute structure	Flack (1983), 1675 Friedel pairs
Absolute structure parameter	−0.03 (2)

Computer programs: APEX2 (Bruker, 2004), APEX2, SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTL.

Selected geometric parameters (Å, º) top

Cu1—O3	1.952 (4)	Cu1—N2ⁱ	2.037 (4)
Cu1—O1	1.960 (4)	Cu1—O5	2.371 (5)
Cu1—N1	2.011 (4)

O3—Cu1—O1	172.88 (18)	O1—Cu1—O5	96.93 (19)
O1—Cu1—N1	91.35 (17)	N1—Cu1—O5	89.59 (17)
O1—Cu1—N2ⁱ	89.17 (17)	N2ⁱ—Cu1—O5	98.15 (18)
O3—Cu1—O5	90.03 (17)

Symmetry code: (i) −x+7/4, y−1/4, z−3/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···O2	0.83	1.96	2.663 (8)	141.5
O5—H2W···O6ⁱⁱ	0.83	1.99	2.795 (8)	163.6
O6—H3W···O4	0.83	1.96	2.730 (7)	153.8
O6—H4W···O1ⁱⁱⁱ	0.85	2.07	2.916 (7)	179.7

Symmetry codes: (ii) −x+7/4, y+1/4, z−1/4; (iii) x−1/4, −y+1/4, z−1/4.

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