Aqua-{6,6-dimeth-oxy-2,2'-[propane-1,3-diylbis(nitrilo-methyl-idyne)]diphenolato-κO,N,N',O'}copper(II) acetonitrile solvate.

In the title compound, [Cu(C(19)H(20)N(2)O(4))(H(2)O)]·C(2)H(3)N, the Cu(II) ion is coordinated by two N and two O atoms from the tetra-dentate Schiff base ligand, which contains a propyl-ene fragment disordered over two conformations in a 0.64 (1):0.36 (1) ratio, and one O atom from the water mol-ecule in a distorted square-pyramidal geometry. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules 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 = 462.98

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.128

S = 1.03

4000 reflections

274 parameters

1 restraint

.

Δρmax = 0.40 e Å−3

Δρmin = −0.58 e Å−3

Absolute structure: Flack (1983 ▶), 1570 Friedel pairs

Flack parameter: 0.00 (2)

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049137/cv2650sup1.cif

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

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

[Cu(C19H20N2O4)(H2O)]·C2H3N	F(000) = 482
Mr = 462.98	Dx = 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

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

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(Fo2) + (0.061P)2 + 0.2306P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.128	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.40 e Å−3
4000 reflections	Δρmin = −0.58 e Å−3
274 parameters	Absolute structure: Flack (1983), 1570 Friedel pairs
1 restraint	Flack parameter: 0.00 (2)
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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

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

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) .