{3-[Bis(2-pyridyl-methyl-κN)amino-κN]propanol}bis-(nitrato-κO)copper(II).

In the title compound, [Cu(NO(3))(2)(C(15)H(19)N(3)O)], the Cu(II) ion is coordinated by the N atoms of the tetra-dentate 3-[bis-(2-pyridyl-meth-yl)amino]-propanol ligand and two O atoms from two monodentate nitrate anions, resulting in a distorted square-pyramidal environment. An inter-molecular O-H⋯O hydrogen-bonding inter-action between the free hy-droxy group of the ligand and a nitrate O atom of an adjacent complex unit, gives a chain structure which extends across the (101) planes.

Related literature

Polyamine complexes have been characterized in order to elucidate the mechanisms of metalloenzymes, see: Tshuva & Lippard (2004 ▶). For complexes with bis­(2-pyridyl­meth­yl)amine ligands, see: Bebout et al. (1998 ▶); Shin et al. (2010 ▶). Compounds with tridentate units have potential biological applications, see: van Staveren et al. (2002 ▶). Palladium(II) and platinum(II) complexes with bis­(2-pyridyl­meth­yl)amine or its derivatives have been investigated as potential anti­cancer agents including cis-platin (Rauterkus et al., 2003 ▶). For the preparation of N,N-bis­(2-pyridyl­meth­yl)-3-amino­propanol, see: Young et al. (1995 ▶).

Experimental

Crystal data

[Cu(NO3)2(C15H19N3O)]

M = 444.89

Monoclinic,

a = 8.3499 (7) Å

b = 14.7703 (12) Å

c = 14.5134 (12) Å

β = 95.055 (2)°

V = 1783.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.28 mm−1

T = 200 K

0.26 × 0.13 × 0.09 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.820, T max = 0.892

13134 measured reflections

4412 independent reflections

2297 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.151

S = 1.04

4412 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.66 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051779/zs2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051779/zs2083Isup2.hkl

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

[Cu(NO3)2(C15H19N3O)]	F(000) = 916
Mr = 444.89	Dx = 1.657 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2504 reflections
a = 8.3499 (7) Å	θ = 2.7–23.6°
b = 14.7703 (12) Å	µ = 1.28 mm−1
c = 14.5134 (12) Å	T = 200 K
β = 95.055 (2)°	Needle, blue-green
V = 1783.0 (3) Å3	0.26 × 0.13 × 0.09 mm
Z = 4

Siemens SMART CCD diffractometer	4412 independent reflections
Radiation source: fine-focus sealed tube	2297 reflections with I > 2σ(I)
graphite	Rint = 0.078
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.820, Tmax = 0.892	k = −19→18
13134 measured reflections	l = −17→19

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0564P)2] where P = (Fo2 + 2Fc2)/3
4412 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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-factorwR and goodness of fit S are based on F2, conventionalR-factors R are based on F, with F set to zero fornegative 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 largeas those based on F, and R- factors based on ALL data will beeven larger.

	x	y	z	Uiso*/Ueq
Cu1	0.13958 (6)	0.34362 (4)	0.87320 (4)	0.03228 (19)
N1	−0.0717 (4)	0.3222 (2)	0.9189 (2)	0.0314 (9)
N2	0.1137 (4)	0.2127 (2)	0.8271 (2)	0.0336 (9)
N3	0.3346 (4)	0.3396 (2)	0.8064 (2)	0.0320 (8)
N4	0.2941 (4)	0.3812 (3)	1.0535 (2)	0.0344 (9)
N5	0.0028 (5)	0.4753 (3)	0.7451 (3)	0.0464 (11)
O1	0.2165 (5)	0.0185 (3)	1.0483 (3)	0.0818 (13)
H1	0.2959	0.0168	1.0880	0.123*
O2	0.2405 (4)	0.4250 (2)	0.9813 (2)	0.0396 (8)
O3	0.2729 (4)	0.2988 (2)	1.0556 (2)	0.0539 (10)
O4	0.3673 (4)	0.4229 (3)	1.1171 (2)	0.0614 (11)
O5	0.0804 (4)	0.4846 (2)	0.8229 (2)	0.0497 (9)
O6	−0.0202 (4)	0.3980 (3)	0.7120 (2)	0.0598 (10)
O7	−0.0504 (5)	0.5423 (3)	0.7013 (3)	0.0789 (13)
C1	−0.1437 (5)	0.3745 (3)	0.9779 (3)	0.0323 (10)
H1A	−0.0927	0.4290	0.9992	0.039*
C2	−0.2890 (5)	0.3519 (3)	1.0086 (3)	0.0373 (11)
H2	−0.3394	0.3908	1.0496	0.045*
C3	−0.3605 (6)	0.2721 (3)	0.9791 (3)	0.0401 (12)
H3	−0.4592	0.2541	1.0015	0.048*
C4	−0.2894 (5)	0.2181 (3)	0.9172 (3)	0.0382 (11)
H4	−0.3384	0.1630	0.8957	0.046*
C5	−0.1448 (5)	0.2458 (3)	0.8868 (3)	0.0335 (10)
C6	−0.0626 (6)	0.1966 (3)	0.8132 (3)	0.0410 (12)
H6A	−0.0849	0.1309	0.8165	0.049*
H6B	−0.1046	0.2186	0.7513	0.049*
C7	0.1975 (6)	0.2068 (3)	0.7424 (3)	0.0427 (12)
H7A	0.1229	0.2238	0.6884	0.051*
H7B	0.2328	0.1436	0.7336	0.051*
C8	0.3421 (5)	0.2690 (3)	0.7485 (3)	0.0361 (11)
C9	0.4694 (6)	0.2583 (3)	0.6956 (3)	0.0451 (13)
H9	0.4763	0.2069	0.6569	0.054*
C10	0.5875 (6)	0.3244 (3)	0.7002 (3)	0.0427 (12)
H10	0.6751	0.3195	0.6629	0.051*
C11	0.5779 (6)	0.3969 (3)	0.7584 (3)	0.0404 (11)
H11	0.6579	0.4427	0.7616	0.049*
C12	0.4513 (5)	0.4020 (3)	0.8115 (3)	0.0341 (10)
H12	0.4458	0.4512	0.8532	0.041*
C13	0.1911 (6)	0.1521 (3)	0.9023 (3)	0.0402 (11)
H13A	0.1480	0.1690	0.9613	0.048*
H13B	0.3079	0.1650	0.9089	0.048*
C14	0.1684 (6)	0.0503 (3)	0.8885 (4)	0.0543 (14)
H14A	0.0536	0.0348	0.8910	0.065*
H14B	0.2000	0.0331	0.8267	0.065*
C15	0.2670 (8)	−0.0015 (4)	0.9608 (4)	0.0659 (17)
H15A	0.2553	−0.0672	0.9485	0.079*
H15B	0.3818	0.0147	0.9594	0.079*

	U11	U22	U33	U12	U13	U23
Cu1	0.0363 (3)	0.0263 (3)	0.0347 (3)	−0.0016 (2)	0.0056 (2)	−0.0041 (2)
N1	0.034 (2)	0.026 (2)	0.034 (2)	−0.0022 (16)	0.0002 (17)	−0.0023 (15)
N2	0.035 (2)	0.033 (2)	0.032 (2)	−0.0039 (17)	0.0023 (17)	−0.0098 (16)
N3	0.033 (2)	0.033 (2)	0.030 (2)	0.0007 (17)	0.0041 (16)	0.0008 (16)
N4	0.037 (2)	0.037 (2)	0.030 (2)	−0.0022 (18)	0.0066 (18)	−0.0032 (18)
N5	0.047 (3)	0.039 (3)	0.054 (3)	0.004 (2)	0.007 (2)	0.010 (2)
O1	0.091 (3)	0.092 (4)	0.063 (3)	0.022 (3)	0.010 (2)	0.003 (2)
O2	0.054 (2)	0.0318 (19)	0.0322 (18)	−0.0032 (15)	0.0001 (15)	−0.0030 (14)
O3	0.073 (3)	0.030 (2)	0.056 (2)	−0.0080 (18)	−0.0066 (19)	0.0031 (17)
O4	0.082 (3)	0.062 (3)	0.037 (2)	−0.020 (2)	−0.0132 (19)	−0.0105 (17)
O5	0.055 (2)	0.053 (2)	0.040 (2)	0.0027 (17)	−0.0047 (18)	0.0028 (16)
O6	0.061 (2)	0.058 (3)	0.059 (2)	−0.009 (2)	0.0001 (19)	−0.001 (2)
O7	0.099 (3)	0.065 (3)	0.070 (3)	0.025 (2)	−0.006 (2)	0.034 (2)
C1	0.033 (3)	0.032 (3)	0.032 (2)	−0.0024 (19)	0.007 (2)	−0.0065 (19)
C2	0.041 (3)	0.036 (3)	0.035 (3)	0.006 (2)	0.002 (2)	−0.003 (2)
C3	0.037 (3)	0.048 (3)	0.036 (3)	−0.003 (2)	0.005 (2)	0.004 (2)
C4	0.042 (3)	0.031 (3)	0.040 (3)	−0.006 (2)	−0.003 (2)	−0.001 (2)
C5	0.035 (3)	0.033 (3)	0.032 (2)	0.003 (2)	0.000 (2)	0.0013 (19)
C6	0.041 (3)	0.036 (3)	0.045 (3)	−0.002 (2)	−0.004 (2)	−0.010 (2)
C7	0.046 (3)	0.039 (3)	0.043 (3)	−0.005 (2)	0.005 (2)	−0.012 (2)
C8	0.042 (3)	0.033 (3)	0.033 (3)	0.003 (2)	0.003 (2)	−0.004 (2)
C9	0.046 (3)	0.052 (3)	0.037 (3)	0.005 (3)	0.007 (2)	−0.012 (2)
C10	0.032 (3)	0.055 (4)	0.042 (3)	0.004 (2)	0.008 (2)	0.001 (2)
C11	0.037 (3)	0.046 (3)	0.038 (3)	0.001 (2)	0.003 (2)	0.006 (2)
C12	0.039 (3)	0.028 (3)	0.034 (3)	−0.002 (2)	−0.001 (2)	0.0002 (19)
C13	0.040 (3)	0.034 (3)	0.046 (3)	0.004 (2)	−0.002 (2)	−0.004 (2)
C14	0.066 (4)	0.038 (3)	0.059 (3)	0.001 (3)	0.004 (3)	−0.002 (2)
C15	0.091 (5)	0.055 (4)	0.053 (4)	0.021 (3)	0.015 (3)	0.008 (3)

Cu1—N1	1.965 (4)	C3—H3	0.9500
Cu1—N3	1.968 (3)	C4—C5	1.383 (6)
Cu1—N2	2.051 (3)	C4—H4	0.9500
Cu1—O2	2.093 (3)	C5—C6	1.507 (6)
Cu1—O5	2.248 (3)	C6—H6A	0.9900
N1—C1	1.335 (5)	C6—H6B	0.9900
N1—C5	1.345 (5)	C7—C8	1.514 (6)
N2—C7	1.469 (5)	C7—H7A	0.9900
N2—C6	1.487 (5)	C7—H7B	0.9900
N2—C13	1.512 (6)	C8—C9	1.374 (6)
N3—C12	1.339 (5)	C9—C10	1.385 (6)
N3—C8	1.343 (5)	C9—H9	0.9500
N4—O4	1.227 (4)	C10—C11	1.370 (6)
N4—O3	1.230 (4)	C10—H10	0.9500
N4—O2	1.279 (4)	C11—C12	1.364 (6)
N5—O7	1.236 (5)	C11—H11	0.9500
N5—O6	1.247 (5)	C12—H12	0.9500
N5—O5	1.259 (5)	C13—C14	1.527 (6)
O1—C15	1.403 (6)	C13—H13A	0.9900
O1—H1	0.8400	C13—H13B	0.9900
C1—C2	1.370 (6)	C14—C15	1.487 (7)
C1—H1A	0.9500	C14—H14A	0.9900
C2—C3	1.373 (6)	C14—H14B	0.9900
C2—H2	0.9500	C15—H15A	0.9900
C3—C4	1.375 (6)	C15—H15B	0.9900
N1—Cu1—N3	165.48 (15)	N2—C6—C5	109.5 (4)
N1—Cu1—N2	83.45 (14)	N2—C6—H6A	109.8
N3—Cu1—N2	83.03 (14)	C5—C6—H6A	109.8
N1—Cu1—O2	98.85 (13)	N2—C6—H6B	109.8
N3—Cu1—O2	95.20 (13)	C5—C6—H6B	109.8
N2—Cu1—O2	144.03 (14)	H6A—C6—H6B	108.2
N1—Cu1—O5	94.64 (13)	N2—C7—C8	110.6 (4)
N3—Cu1—O5	92.06 (14)	N2—C7—H7A	109.5
N2—Cu1—O5	138.91 (14)	C8—C7—H7A	109.5
O2—Cu1—O5	76.95 (12)	N2—C7—H7B	109.5
C1—N1—C5	119.4 (4)	C8—C7—H7B	109.5
C1—N1—Cu1	126.3 (3)	H7A—C7—H7B	108.1
C5—N1—Cu1	114.3 (3)	N3—C8—C9	121.3 (4)
C7—N2—C6	114.5 (4)	N3—C8—C7	115.2 (4)
C7—N2—C13	111.3 (4)	C9—C8—C7	123.4 (4)
C6—N2—C13	111.0 (3)	C8—C9—C10	118.4 (4)
C7—N2—Cu1	106.5 (3)	C8—C9—H9	120.8
C6—N2—Cu1	105.6 (3)	C10—C9—H9	120.8
C13—N2—Cu1	107.2 (3)	C11—C10—C9	120.0 (4)
C12—N3—C8	119.6 (4)	C11—C10—H10	120.0
C12—N3—Cu1	125.6 (3)	C9—C10—H10	120.0
C8—N3—Cu1	114.7 (3)	C12—C11—C10	118.8 (5)
O4—N4—O3	122.8 (4)	C12—C11—H11	120.6
O4—N4—O2	118.5 (4)	C10—C11—H11	120.6
O3—N4—O2	118.6 (4)	N3—C12—C11	121.8 (4)
O7—N5—O6	119.9 (5)	N3—C12—H12	119.1
O7—N5—O5	120.4 (5)	C11—C12—H12	119.1
O6—N5—O5	119.7 (4)	N2—C13—C14	116.6 (4)
C15—O1—H1	109.5	N2—C13—H13A	108.1
N4—O2—Cu1	114.4 (3)	C14—C13—H13A	108.1
N5—O5—Cu1	105.7 (3)	N2—C13—H13B	108.1
N1—C1—C2	122.0 (4)	C14—C13—H13B	108.1
N1—C1—H1A	119.0	H13A—C13—H13B	107.3
C2—C1—H1A	119.0	C15—C14—C13	111.1 (4)
C1—C2—C3	118.7 (4)	C15—C14—H14A	109.4
C1—C2—H2	120.7	C13—C14—H14A	109.4
C3—C2—H2	120.7	C15—C14—H14B	109.4
C2—C3—C4	120.1 (4)	C13—C14—H14B	109.4
C2—C3—H3	119.9	H14A—C14—H14B	108.0
C4—C3—H3	119.9	O1—C15—C14	109.8 (5)
C3—C4—C5	118.4 (4)	O1—C15—H15A	109.7
C3—C4—H4	120.8	C14—C15—H15A	109.7
C5—C4—H4	120.8	O1—C15—H15B	109.7
N1—C5—C4	121.4 (4)	C14—C15—H15B	109.7
N1—C5—C6	115.4 (4)	H15A—C15—H15B	108.2
C4—C5—C6	123.2 (4)
N3—Cu1—N1—C1	−171.0 (5)	O2—Cu1—O5—N5	−179.4 (3)
N2—Cu1—N1—C1	167.4 (4)	C5—N1—C1—C2	1.4 (6)
O2—Cu1—N1—C1	23.7 (4)	Cu1—N1—C1—C2	−177.4 (3)
O5—Cu1—N1—C1	−53.8 (4)	N1—C1—C2—C3	1.4 (7)
N3—Cu1—N1—C5	10.1 (8)	C1—C2—C3—C4	−2.4 (7)
N2—Cu1—N1—C5	−11.4 (3)	C2—C3—C4—C5	0.8 (7)
O2—Cu1—N1—C5	−155.2 (3)	C1—N1—C5—C4	−3.2 (6)
O5—Cu1—N1—C5	127.4 (3)	Cu1—N1—C5—C4	175.8 (3)
N1—Cu1—N2—C7	148.6 (3)	C1—N1—C5—C6	173.8 (4)
N3—Cu1—N2—C7	−26.0 (3)	Cu1—N1—C5—C6	−7.3 (5)
O2—Cu1—N2—C7	−115.3 (3)	C3—C4—C5—N1	2.1 (7)
O5—Cu1—N2—C7	59.1 (4)	C3—C4—C5—C6	−174.6 (4)
N1—Cu1—N2—C6	26.4 (3)	C7—N2—C6—C5	−152.9 (4)
N3—Cu1—N2—C6	−148.3 (3)	C13—N2—C6—C5	79.9 (4)
O2—Cu1—N2—C6	122.5 (3)	Cu1—N2—C6—C5	−36.0 (4)
O5—Cu1—N2—C6	−63.1 (3)	N1—C5—C6—N2	30.1 (5)
N1—Cu1—N2—C13	−92.1 (3)	C4—C5—C6—N2	−153.0 (4)
N3—Cu1—N2—C13	93.3 (3)	C6—N2—C7—C8	149.5 (4)
O2—Cu1—N2—C13	4.0 (4)	C13—N2—C7—C8	−83.5 (4)
O5—Cu1—N2—C13	178.4 (2)	Cu1—N2—C7—C8	33.1 (4)
N1—Cu1—N3—C12	169.3 (5)	C12—N3—C8—C9	1.5 (6)
N2—Cu1—N3—C12	−169.2 (4)	Cu1—N3—C8—C9	178.5 (3)
O2—Cu1—N3—C12	−25.3 (4)	C12—N3—C8—C7	−175.2 (4)
O5—Cu1—N3—C12	51.7 (3)	Cu1—N3—C8—C7	1.8 (5)
N1—Cu1—N3—C8	−7.5 (8)	N2—C7—C8—N3	−24.4 (6)
N2—Cu1—N3—C8	14.0 (3)	N2—C7—C8—C9	159.0 (4)
O2—Cu1—N3—C8	157.9 (3)	N3—C8—C9—C10	−2.8 (7)
O5—Cu1—N3—C8	−125.0 (3)	C7—C8—C9—C10	173.6 (4)
O4—N4—O2—Cu1	173.9 (3)	C8—C9—C10—C11	1.8 (7)
O3—N4—O2—Cu1	−4.6 (5)	C9—C10—C11—C12	0.4 (7)
N1—Cu1—O2—N4	79.6 (3)	C8—N3—C12—C11	0.8 (6)
N3—Cu1—O2—N4	−96.7 (3)	Cu1—N3—C12—C11	−175.8 (3)
N2—Cu1—O2—N4	−11.4 (4)	C10—C11—C12—N3	−1.8 (7)
O5—Cu1—O2—N4	172.4 (3)	C7—N2—C13—C14	−71.2 (5)
O7—N5—O5—Cu1	177.9 (4)	C6—N2—C13—C14	57.7 (5)
O6—N5—O5—Cu1	−2.2 (5)	Cu1—N2—C13—C14	172.7 (3)
N1—Cu1—O5—N5	−81.4 (3)	N2—C13—C14—C15	172.9 (4)
N3—Cu1—O5—N5	85.7 (3)	C13—C14—C15—O1	62.6 (6)
N2—Cu1—O5—N5	3.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7i	0.84	2.18	2.961 (6)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O7i	0.84	2.18	2.961 (6)	155

Symmetry code: (i) .