Aqua­{6,6-dimeth­oxy-2,2′-[propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato-κ4O,N,N′,O′}copper(II) acetonitrile solvate

Wang, X.

doi:10.1107/S1600536809049137

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1658

doi:10.1107/S1600536809049137

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Aqua{6,6-dimethoxy-2,2′-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato-κ⁴O,N,N′,O′}copper(II) acetonitrile solvate

Xinfang Wang ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou 253023, People's Republic of China
^*Correspondence e-mail: dzxfwang@yahoo.com.cn

(Received 30 October 2009; accepted 18 November 2009; online 21 November 2009)

In the title compound, [Cu(C₁₉H₂₀N₂O₄)(H₂O)]·C₂H₃N, the Cu^II ion is coordinated by two N and two O atoms from the tetradentate Schiff base ligand, which contains a propylene fragment disordered over two conformations in a 0.64 (1):0.36 (1) ratio, and one O atom from the water molecule in a distorted square-pyramidal geometry. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into chains along the a axis.

Related literature

For related crystal structures, see: Nathan et al. (2003 ); Saha et al. (2007 ); Xing (2009 ).

Experimental

Crystal data

[Cu(C₁₉H₂₀N₂O₄)(H₂O)]·C₂H₃N
M_r = 462.98
Monoclinic, P 2₁
a = 5.4003 (9) Å
b = 19.155 (4) Å
c = 10.3891 (18) Å
β = 98.862 (3)°
V = 1061.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.07 mm⁻¹
T = 273 K
0.15 × 0.13 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.857, T_max = 0.910
6127 measured reflections
4000 independent reflections
3145 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.128
S = 1.03
4000 reflections
274 parameters
1 restraint
.
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.58 e Å⁻³
Absolute structure: Flack (1983 ), 1570 Friedel pairs
Flack parameter: 0.00 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱ	0.82	2.33	3.055 (6)	148
O3—H3A⋯O5ⁱ	0.82	2.12	2.805 (6)	140
O3—H3B⋯O1ⁱ	0.82	2.53	3.048 (5)	122
O3—H3B⋯O4ⁱ	0.82	2.00	2.805 (6)	166
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); 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/S1600536809049137/cv2650sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049137/cv2650Isup2.hkl

checkCIF report

Comment top

In continuation of our studies of tetradentate Shiff-base ligands and their complexes (Xing, 2009), we present here the title compound, (I).

In (I) (Fig. 1), the coordination sphere of the Cu^II ion can be described as a distorted square-pyramidal one, in which the four basal positions are occupied by two N atoms and two O atoms from the tetradentate Schiff-base ligand, and the fifth apical site is occupied by the O atom of the coordinated water molecule. The Cu^II ion is out of the plane formed by N₂O₂ unit at 0.102Å towards the Cu—O_H2_O bond. The average Cu—N, Cu—O_{Schiff base}, and the Cu—O_aqua bond lengths are 2.017 (4), 1.956 (4) and 2.276 (4) Å, respectively, which are all in agreement with the corresponding distances found in others Schiff base complexes with Cu (Nathan, et al., 2003; Saha, et al., 2007; Xing, 2009).

Intermolecular O—H···O hydrogen bonds (Table 1) link molecules related by translation along axis a into chains.

Related literature top

For related crystal structures, see: Nathan et al. (2003); Saha et al. (2007); Xing (2009).

Experimental top

The Schiff base ligand was synthesized by condensation of propyl diamine and 3-methoxyl-2-hydroxy-benzaldehyde with the ratio 1:2 in ethanol. The title complex was synthesized by reacting Cu(ClO₄)₂.6H₂O and the schiff-base ligand (1:1, molar ratio) in acetonitrile. The mixture was stirred for for about 10 min at room temperature, then filtered, and then the filtrate was allowed to slow evaporate undisturbed for ten days to afford blue crystals suitable for X-ray diffraction with a yield about 60%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Only major part of the disordered atom C10 is shown. H-atoms are omitted for clarity.

Aqua{6,6-dimethoxy-2,2'-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato- κ⁴O,N,N',O'}copper(II) acetonitrile solvate top

Crystal data top

[Cu(C₁₉H₂₀N₂O₄)(H₂O)]·C₂H₃N	F(000) = 482
M_r = 462.98	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.4003 (9) Å	Cell parameters from 1983 reflections
b = 19.155 (4) Å	θ = 2.9–22.0°
c = 10.3891 (18) Å	µ = 1.07 mm⁻¹
β = 98.862 (3)°	T = 273 K
V = 1061.8 (3) Å³	Block, green
Z = 2	0.15 × 0.13 × 0.09 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4000 independent reflections
Radiation source: fine-focus sealed tube	3145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −6→7
T_min = 0.857, T_max = 0.910	k = −17→24
6127 measured reflections	l = −13→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.061P)² + 0.2306P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.128	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.40 e Å⁻³
4000 reflections	Δρ_min = −0.58 e Å⁻³
274 parameters	Absolute structure: Flack (1983), 1570 Friedel pairs
1 restraint	Absolute structure parameter: 0.00 (2)
Primary atom site location: structure-invariant direct methods

Crystal data top

[Cu(C₁₉H₂₀N₂O₄)(H₂O)]·C₂H₃N	V = 1061.8 (3) Å³
M_r = 462.98	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.4003 (9) Å	µ = 1.07 mm⁻¹
b = 19.155 (4) Å	T = 273 K
c = 10.3891 (18) Å	0.15 × 0.13 × 0.09 mm
β = 98.862 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4000 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	3145 reflections with I > 2σ(I)
T_min = 0.857, T_max = 0.910	R_int = 0.027
6127 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.128	Δρ_max = 0.40 e Å⁻³
S = 1.03	Δρ_min = −0.58 e Å⁻³
4000 reflections	Absolute structure: Flack (1983), 1570 Friedel pairs
274 parameters	Absolute structure parameter: 0.00 (2)

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	Occ. (<1)
Cu1	0.91053 (9)	0.74577 (4)	0.52909 (5)	0.04410 (17)
N1	1.0195 (8)	0.7458 (5)	0.3513 (4)	0.0637 (11)
N2	1.1012 (9)	0.8326 (3)	0.5920 (5)	0.0580 (12)
O1	0.6757 (7)	0.6700 (2)	0.4746 (3)	0.0532 (9)
O2	0.7350 (5)	0.7475 (3)	0.6805 (3)	0.0516 (7)
O3	1.2273 (8)	0.6746 (2)	0.6203 (4)	0.0565 (10)
H3B	1.2752	0.6483	0.5667	0.06 (2)*
H3A	1.3426	0.6950	0.6659	0.09 (3)*
O4	0.3574 (8)	0.5659 (2)	0.4627 (5)	0.0743 (12)
O5	0.4665 (8)	0.7216 (2)	0.8637 (4)	0.0733 (14)
C1	0.4793 (10)	0.5744 (3)	0.3569 (5)	0.0539 (13)
C2	0.6506 (9)	0.6313 (3)	0.3692 (5)	0.0481 (12)
C3	0.7817 (11)	0.6420 (3)	0.2649 (5)	0.0573 (14)
C4	0.7478 (14)	0.5969 (4)	0.1560 (6)	0.0737 (19)
H4	0.8411	0.6038	0.0889	0.088*
C5	0.5837 (14)	0.5444 (4)	0.1482 (6)	0.0773 (19)
H5	0.5608	0.5160	0.0748	0.093*
C6	0.4434 (13)	0.5316 (3)	0.2509 (6)	0.0653 (16)
H6	0.3297	0.4949	0.2458	0.078*
C7	0.9537 (11)	0.6988 (4)	0.2631 (5)	0.0657 (16)
H7	1.0280	0.7025	0.1884	0.079*
C8	0.1745 (12)	0.5122 (4)	0.4587 (7)	0.0771 (18)
H8A	0.2316	0.4714	0.4184	0.116*
H8B	0.0197	0.5279	0.4092	0.116*
H8C	0.1488	0.5011	0.5458	0.116*
C9	1.2883 (16)	0.8635 (5)	0.5191 (8)	0.0919 (16)	0.355 (10)
H9A	1.2233	0.9085	0.4871	0.110*	0.355 (10)
H9B	1.4374	0.8727	0.5817	0.110*	0.355 (10)
C9'	1.2883 (16)	0.8635 (5)	0.5191 (8)	0.0919 (16)	0.645 (10)
H9'1	1.4433	0.8373	0.5373	0.110*	0.645 (10)
H9'2	1.3227	0.9112	0.5482	0.110*	0.645 (10)
C10	1.365 (3)	0.8290 (10)	0.4150 (19)	0.073 (3)	0.355 (10)
H10A	1.4880	0.7950	0.4531	0.088*	0.355 (10)
H10B	1.4563	0.8633	0.3720	0.088*	0.355 (10)
C10A	1.198 (2)	0.8632 (5)	0.3764 (10)	0.073 (3)	0.645 (10)
H10C	1.0257	0.8792	0.3608	0.088*	0.645 (10)
H10D	1.2976	0.8960	0.3348	0.088*	0.645 (10)
C11	1.2121 (15)	0.7941 (5)	0.3158 (7)	0.0919 (16)	0.355 (10)
H11A	1.3195	0.7677	0.2669	0.110*	0.355 (10)
H11B	1.1271	0.8289	0.2572	0.110*	0.355 (10)
C11'	1.2121 (15)	0.7941 (5)	0.3158 (7)	0.0919 (16)	0.645 (10)
H11C	1.3770	0.7743	0.3435	0.110*	0.645 (10)
H11D	1.1891	0.7993	0.2219	0.110*	0.645 (10)
C12	1.0861 (11)	0.8625 (3)	0.7019 (6)	0.0601 (14)
H12	1.1902	0.9010	0.7216	0.072*
C13	0.9337 (11)	0.8453 (3)	0.7972 (5)	0.0549 (13)
C14	0.7679 (9)	0.7890 (3)	0.7800 (5)	0.0481 (12)
C15	0.6222 (10)	0.7774 (3)	0.8845 (5)	0.0575 (14)
C16	0.6491 (12)	0.8209 (4)	0.9914 (5)	0.0717 (18)
H16	0.5529	0.8129	1.0568	0.086*
C17	0.8133 (16)	0.8756 (4)	1.0037 (6)	0.086 (2)
H17	0.8263	0.9044	1.0765	0.103*
C18	0.9574 (14)	0.8881 (4)	0.9103 (6)	0.0734 (17)
H18	1.0719	0.9246	0.9202	0.088*
C19	0.3062 (12)	0.7070 (4)	0.9568 (6)	0.079 (2)
H19A	0.1994	0.7464	0.9638	0.119*
H19B	0.4055	0.6979	1.0399	0.119*
H19C	0.2053	0.6668	0.9294	0.119*
N3	0.4416 (17)	0.4878 (4)	0.7839 (7)	0.118 (3)
C20	0.7826 (12)	0.5758 (4)	0.7570 (7)	0.0726 (17)
H20A	0.7975	0.5791	0.6663	0.109*
H20B	0.9394	0.5608	0.8054	0.109*
H20C	0.7394	0.6207	0.7881	0.109*
C21	0.5916 (15)	0.5266 (4)	0.7737 (6)	0.0719 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0424 (3)	0.0463 (3)	0.0456 (3)	−0.0022 (4)	0.01310 (18)	−0.0013 (4)
N1	0.069 (2)	0.077 (3)	0.047 (2)	−0.014 (4)	0.0168 (17)	0.007 (4)
N2	0.060 (3)	0.045 (3)	0.071 (3)	−0.002 (2)	0.017 (2)	0.002 (2)
O1	0.0527 (19)	0.061 (2)	0.0478 (19)	−0.0123 (18)	0.0157 (15)	−0.0158 (17)
O2	0.0521 (15)	0.0582 (19)	0.0477 (16)	−0.009 (3)	0.0178 (12)	−0.016 (3)
O3	0.055 (2)	0.056 (2)	0.059 (2)	0.008 (2)	0.011 (2)	−0.006 (2)
O4	0.071 (3)	0.070 (3)	0.087 (3)	−0.025 (2)	0.028 (2)	−0.027 (2)
O5	0.065 (2)	0.107 (4)	0.053 (2)	−0.016 (2)	0.0255 (19)	−0.013 (2)
C1	0.053 (3)	0.049 (3)	0.058 (3)	0.005 (2)	0.000 (2)	−0.009 (2)
C2	0.041 (3)	0.052 (3)	0.051 (3)	0.010 (2)	0.005 (2)	−0.004 (2)
C3	0.068 (3)	0.067 (4)	0.037 (2)	0.018 (3)	0.009 (2)	0.001 (2)
C4	0.093 (5)	0.079 (5)	0.049 (3)	0.019 (4)	0.013 (3)	−0.008 (3)
C5	0.105 (5)	0.060 (4)	0.064 (4)	0.010 (4)	0.003 (4)	−0.020 (3)
C6	0.069 (4)	0.051 (4)	0.073 (4)	0.013 (3)	0.001 (3)	−0.012 (3)
C7	0.069 (4)	0.088 (5)	0.044 (3)	0.002 (3)	0.023 (3)	0.007 (3)
C8	0.067 (4)	0.056 (4)	0.109 (5)	−0.014 (3)	0.017 (4)	−0.014 (4)
C9	0.101 (4)	0.092 (4)	0.091 (4)	−0.037 (3)	0.039 (3)	−0.004 (3)
C9'	0.101 (4)	0.092 (4)	0.091 (4)	−0.037 (3)	0.039 (3)	−0.004 (3)
C10	0.075 (6)	0.062 (6)	0.089 (6)	−0.005 (4)	0.031 (5)	0.034 (5)
C10A	0.075 (6)	0.062 (6)	0.089 (6)	−0.005 (4)	0.031 (5)	0.034 (5)
C11	0.101 (4)	0.092 (4)	0.091 (4)	−0.037 (3)	0.039 (3)	−0.004 (3)
C11'	0.101 (4)	0.092 (4)	0.091 (4)	−0.037 (3)	0.039 (3)	−0.004 (3)
C12	0.065 (3)	0.038 (3)	0.075 (4)	−0.005 (3)	0.006 (3)	−0.005 (3)
C13	0.062 (3)	0.041 (3)	0.059 (3)	0.009 (3)	0.000 (3)	−0.005 (2)
C14	0.045 (3)	0.054 (3)	0.044 (3)	0.011 (2)	0.004 (2)	0.001 (2)
C15	0.050 (3)	0.072 (4)	0.050 (3)	0.011 (3)	0.006 (2)	−0.007 (2)
C16	0.076 (4)	0.099 (6)	0.040 (3)	0.017 (4)	0.010 (3)	−0.010 (3)
C17	0.124 (6)	0.078 (5)	0.054 (4)	0.020 (5)	0.004 (4)	−0.023 (3)
C18	0.101 (5)	0.051 (4)	0.065 (4)	0.006 (4)	0.001 (4)	−0.013 (3)
C19	0.068 (4)	0.116 (6)	0.058 (3)	0.007 (4)	0.026 (3)	0.019 (4)
N3	0.153 (7)	0.114 (7)	0.096 (5)	−0.044 (6)	0.046 (5)	0.025 (5)
C20	0.081 (4)	0.061 (4)	0.079 (4)	0.004 (3)	0.024 (3)	0.010 (3)
C21	0.109 (5)	0.065 (4)	0.047 (3)	0.002 (4)	0.031 (3)	0.007 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.954 (4)	C8—H8C	0.9600
Cu1—O2	1.958 (3)	C9—C10	1.39 (2)
Cu1—N2	2.012 (5)	C9—H9A	0.9700
Cu1—N1	2.023 (4)	C9—H9B	0.9700
Cu1—O3	2.276 (4)	C10—C11	1.39 (2)
N1—C7	1.294 (9)	C10—H10A	0.9700
N1—C11	1.480 (9)	C10—H10B	0.9700
N2—C12	1.292 (7)	C10A—H10C	0.9700
N2—C9	1.476 (8)	C10A—H10D	0.9700
O1—C2	1.311 (6)	C11—H11A	0.9700
O2—C14	1.294 (7)	C11—H11B	0.9700
O3—H3B	0.8219	C12—C13	1.420 (8)
O3—H3A	0.8213	C12—H12	0.9300
O4—C1	1.375 (6)	C13—C14	1.396 (8)
O4—C8	1.421 (7)	C13—C18	1.422 (8)
O5—C15	1.357 (7)	C14—C15	1.453 (7)
O5—C19	1.422 (6)	C15—C16	1.378 (9)
C1—C6	1.363 (8)	C16—C17	1.365 (11)
C1—C2	1.422 (8)	C16—H16	0.9300
C2—C3	1.399 (7)	C17—C18	1.355 (9)
C3—C4	1.413 (8)	C17—H17	0.9300
C3—C7	1.433 (9)	C18—H18	0.9300
C4—C5	1.334 (10)	C19—H19A	0.9600
C4—H4	0.9300	C19—H19B	0.9600
C5—C6	1.422 (9)	C19—H19C	0.9600
C5—H5	0.9300	N3—C21	1.117 (9)
C6—H6	0.9300	C20—C21	1.428 (9)
C7—H7	0.9300	C20—H20A	0.9600
C8—H8A	0.9600	C20—H20B	0.9600
C8—H8B	0.9600	C20—H20C	0.9600

O1—Cu1—O2	82.67 (17)	N2—C9—H9A	107.0
O1—Cu1—N2	170.30 (18)	C10—C9—H9B	107.0
O2—Cu1—N2	90.7 (2)	N2—C9—H9B	107.0
O1—Cu1—N1	90.2 (2)	H9A—C9—H9B	106.7
O2—Cu1—N1	168.09 (15)	C9—C10—C11	126.4 (14)
N2—Cu1—N1	95.2 (3)	C9—C10—H10A	105.7
O1—Cu1—O3	95.05 (17)	C11—C10—H10A	105.7
O2—Cu1—O3	95.83 (17)	C9—C10—H10B	105.7
N2—Cu1—O3	92.6 (2)	C11—C10—H10B	105.7
N1—Cu1—O3	94.3 (2)	H10A—C10—H10B	106.2
C7—N1—C11	112.6 (5)	H10C—C10A—H10D	107.7
C7—N1—Cu1	124.0 (5)	C10—C11—N1	118.5 (8)
C11—N1—Cu1	122.8 (5)	C10—C11—H11A	107.7
C12—N2—C9	114.6 (6)	N1—C11—H11A	107.7
C12—N2—Cu1	123.7 (4)	C10—C11—H11B	107.7
C9—N2—Cu1	121.4 (4)	N1—C11—H11B	107.7
C2—O1—Cu1	129.8 (3)	H11A—C11—H11B	107.1
C14—O2—Cu1	129.0 (4)	N2—C12—C13	129.4 (6)
Cu1—O3—H3B	112.4	N2—C12—H12	115.3
Cu1—O3—H3A	114.2	C13—C12—H12	115.3
H3B—O3—H3A	113.1	C14—C13—C12	121.4 (5)
C1—O4—C8	118.6 (5)	C14—C13—C18	121.7 (6)
C15—O5—C19	118.2 (5)	C12—C13—C18	117.0 (6)
C6—C1—O4	123.3 (6)	O2—C14—C13	125.6 (5)
C6—C1—C2	122.9 (6)	O2—C14—C15	118.7 (5)
O4—C1—C2	113.8 (4)	C13—C14—C15	115.7 (5)
O1—C2—C3	124.4 (5)	O5—C15—C16	126.3 (6)
O1—C2—C1	119.3 (4)	O5—C15—C14	113.2 (5)
C3—C2—C1	116.3 (5)	C16—C15—C14	120.5 (6)
C2—C3—C4	120.8 (6)	C17—C16—C15	121.8 (6)
C2—C3—C7	121.9 (5)	C17—C16—H16	119.1
C4—C3—C7	117.3 (6)	C15—C16—H16	119.1
C5—C4—C3	120.8 (6)	C18—C17—C16	120.3 (6)
C5—C4—H4	119.6	C18—C17—H17	119.9
C3—C4—H4	119.6	C16—C17—H17	119.9
C4—C5—C6	120.7 (6)	C17—C18—C13	120.1 (7)
C4—C5—H5	119.7	C17—C18—H18	119.9
C6—C5—H5	119.6	C13—C18—H18	119.9
C1—C6—C5	118.5 (7)	O5—C19—H19A	109.5
C1—C6—H6	120.8	O5—C19—H19B	109.5
C5—C6—H6	120.8	H19A—C19—H19B	109.5
N1—C7—C3	128.8 (5)	O5—C19—H19C	109.5
N1—C7—H7	115.6	H19A—C19—H19C	109.5
C3—C7—H7	115.6	H19B—C19—H19C	109.5
O4—C8—H8A	109.5	C21—C20—H20A	109.5
O4—C8—H8B	109.5	C21—C20—H20B	109.5
H8A—C8—H8B	109.5	H20A—C20—H20B	109.5
O4—C8—H8C	109.5	C21—C20—H20C	109.5
H8A—C8—H8C	109.5	H20A—C20—H20C	109.5
H8B—C8—H8C	109.5	H20B—C20—H20C	109.5
C10—C9—N2	121.3 (9)	N3—C21—C20	178.5 (8)
C10—C9—H9A	107.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.82	2.33	3.055 (6)	148
O3—H3A···O5ⁱ	0.82	2.12	2.805 (6)	140
O3—H3B···O1ⁱ	0.82	2.53	3.048 (5)	122
O3—H3B···O4ⁱ	0.82	2.00	2.805 (6)	166

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₉H₂₀N₂O₄)(H₂O)]·C₂H₃N
M_r	462.98
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	273
a, b, c (Å)	5.4003 (9), 19.155 (4), 10.3891 (18)
β (°)	98.862 (3)
V (Å³)	1061.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.07
Crystal size (mm)	0.15 × 0.13 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.857, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	6127, 4000, 3145
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.128, 1.03
No. of reflections	4000
No. of parameters	274
No. of restraints	1
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.58
Absolute structure	Flack (1983), 1570 Friedel pairs
Absolute structure parameter	0.00 (2)

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), 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
O3—H3A···O2ⁱ	0.82	2.33	3.055 (6)	147.7
O3—H3A···O5ⁱ	0.82	2.12	2.805 (6)	140.4
O3—H3B···O1ⁱ	0.82	2.53	3.048 (5)	122.1
O3—H3B···O4ⁱ	0.82	2.00	2.805 (6)	165.7

Symmetry code: (i) x+1, y, z.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nathan, L. C., Koehne, J. E., Gilmore, J. M., Hannibal, K. A., Dewhirst, W. E. & Mai, T. D. (2003). Polyhedron, 22, 887–894. Web of Science CSD CrossRef CAS Google Scholar
Saha, P. K., Dutta, B., Jana, S., Bera, R., Saha, S., Okamoto, K. & Koner, S. (2007). Polyhedron, 26, 563–571. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xing, J. (2009). Acta Cryst. E65, m469. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Page m1658

doi:10.1107/S1600536809049137

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