(11,13-Dimethyl-1,4,7,10-tetra-azacyclo-trideca-10,13-dienato)copper(II) per-chlorate.

The title complex, [Cu(C(11)H(21)N(4))]ClO(4), comprises [Cu(II)(L)](+) (L = 11,13-dimethyl-1,4,7,10-tetra-azacyclo-trideca-10,12-dien-ate) cations and a perchlorate anion. The Cu atom is located on a twofold crystallographic symmetry axis and is coordinated by four N atoms in a slightly distorted square-planar geometry. Inter-molecular N-H⋯O hydrogen bonds are present.

Related literature

For macrocyclic ligands containing four N atoms in a square-planar coordination geometry, see: Andrews et al. (1999 ▶); Kim et al. (2004 ▶); Richardson & Sievers (1972 ▶).

Experimental

Crystal data

[Cu(C11H21N4)]ClO4

M = 372.31

Orthorhombic,

a = 12.530 (5) Å

b = 14.469 (6) Å

c = 8.501 (4) Å

V = 1541.2 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.61 mm−1

T = 293 (2) K

0.15 × 0.13 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.794, T max = 0.843

6834 measured reflections

1349 independent reflections

950 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.216

S = 1.05

1349 reflections

98 parameters

H-atom parameters constrained

Δρmax = 1.10 e Å−3

Δρmin = −0.59 e Å−3

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: XP (Sheldrick, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001664/hg2468sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001664/hg2468Isup2.hkl

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

[Cu(C11H21N4)]ClO4	F(000) = 772
Mr = 372.31	Dx = 1.605 Mg m−3Dm = 1.605 Mg m−3Dm measured by not measured
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1838 reflections
a = 12.530 (5) Å	θ = 3.2–24.7°
b = 14.469 (6) Å	µ = 1.61 mm−1
c = 8.501 (4) Å	T = 293 K
V = 1541.2 (11) Å3	Block, blue
Z = 4	0.15 × 0.13 × 0.11 mm

Bruker APEXII CCD area-detector diffractometer	1349 independent reflections
Radiation source: fine-focus sealed tube	950 reflections with I > 2σ(I)
graphite	Rint = 0.064
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→12
Tmin = 0.794, Tmax = 0.843	k = −15→17
6834 measured reflections	l = −9→10

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.144P)2 + 0.9336P] where P = (Fo2 + 2Fc2)/3
1349 reflections	(Δ/σ)max < 0.001
98 parameters	Δρmax = 1.10 e Å−3
0 restraints	Δρmin = −0.59 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 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
Cu1	0.0000	0.32069 (5)	0.2500	0.0431 (4)
Cl1	0.0000	0.14239 (18)	0.7500	0.0660 (7)
O1	0.0525 (6)	0.2000 (6)	0.6429 (9)	0.139 (3)
O2	0.0806 (8)	0.0904 (4)	0.8238 (11)	0.160 (3)
N1	0.0904 (3)	0.4014 (3)	0.1568 (5)	0.0481 (11)
N2	0.0740 (3)	0.2278 (3)	0.1414 (5)	0.0476 (11)
H2	0.0427	0.2219	0.0453	0.057*
C1	0.0000	0.5334 (6)	0.2500	0.060 (2)
H1	0.0000	0.5976	0.2500	0.072*
C2	0.0803 (4)	0.4932 (3)	0.1651 (7)	0.0579 (15)
C3	0.1590 (5)	0.5506 (4)	0.0804 (9)	0.078 (2)
H3A	0.2298	0.5334	0.1122	0.117*
H3B	0.1471	0.6146	0.1047	0.117*
H3C	0.1513	0.5412	−0.0308	0.117*
C4	0.1727 (4)	0.3589 (4)	0.0637 (7)	0.0576 (14)
H4A	0.2396	0.3916	0.0780	0.069*
H4B	0.1537	0.3613	−0.0469	0.069*
C5	0.1840 (4)	0.2618 (4)	0.1151 (8)	0.0597 (14)
H5A	0.2253	0.2581	0.2114	0.072*
H5B	0.2193	0.2254	0.0347	0.072*
C6	0.0587 (5)	0.1407 (4)	0.2241 (7)	0.0574 (15)
H6A	0.1056	0.1369	0.3147	0.069*
H6B	0.0732	0.0888	0.1552	0.069*

	U11	U22	U33	U12	U13	U23
Cu1	0.0446 (7)	0.0320 (6)	0.0526 (7)	0.000	−0.0004 (3)	0.000
Cl1	0.0883 (17)	0.0572 (14)	0.0526 (13)	0.000	0.0019 (10)	0.000
O1	0.113 (5)	0.182 (6)	0.122 (6)	−0.012 (5)	−0.020 (4)	0.056 (5)
O2	0.244 (10)	0.106 (4)	0.130 (6)	0.077 (6)	−0.015 (7)	0.003 (5)
N1	0.045 (2)	0.039 (2)	0.060 (3)	−0.0019 (17)	−0.004 (2)	0.0077 (19)
N2	0.055 (3)	0.038 (2)	0.049 (2)	0.0060 (18)	0.0024 (19)	0.0023 (17)
C1	0.069 (5)	0.022 (3)	0.090 (7)	0.000	−0.026 (5)	0.000
C2	0.058 (3)	0.041 (3)	0.075 (4)	−0.011 (3)	−0.031 (3)	0.012 (3)
C3	0.078 (4)	0.051 (3)	0.104 (5)	−0.027 (3)	−0.026 (4)	0.020 (3)
C4	0.048 (3)	0.057 (3)	0.068 (4)	−0.002 (2)	0.006 (3)	0.011 (3)
C5	0.053 (3)	0.059 (3)	0.068 (4)	0.010 (2)	0.002 (3)	0.008 (3)
C6	0.070 (4)	0.034 (3)	0.068 (4)	0.007 (3)	0.002 (3)	0.004 (2)

Cu1—N1i	1.809 (4)	C1—C2i	1.367 (7)
Cu1—N1	1.809 (4)	C1—H1	0.9300
Cu1—N2i	1.876 (4)	C2—C3	1.477 (8)
Cu1—N2	1.876 (4)	C3—H3A	0.9600
Cl1—O1ii	1.399 (8)	C3—H3B	0.9600
Cl1—O1	1.399 (8)	C3—H3C	0.9600
Cl1—O2	1.407 (8)	C4—C5	1.479 (8)
Cl1—O2ii	1.407 (8)	C4—H4A	0.9700
N1—C2	1.337 (6)	C4—H4B	0.9700
N1—C4	1.438 (7)	C5—H5A	0.9700
N2—C6	1.455 (7)	C5—H5B	0.9700
N2—C5	1.481 (7)	C6—C6i	1.535 (13)
N2—H2	0.9100	C6—H6A	0.9700
C1—C2	1.367 (7)	C6—H6B	0.9700
N1i—Cu1—N1	99.6 (3)	C1—C2—C3	120.7 (5)
N1i—Cu1—N2i	86.43 (19)	C2—C3—H3A	109.5
N1—Cu1—N2i	170.85 (17)	C2—C3—H3B	109.5
N1i—Cu1—N2	170.85 (17)	H3A—C3—H3B	109.5
N1—Cu1—N2	86.43 (19)	C2—C3—H3C	109.5
N2i—Cu1—N2	88.4 (2)	H3A—C3—H3C	109.5
O1ii—Cl1—O1	106.9 (7)	H3B—C3—H3C	109.5
O1ii—Cl1—O2	111.4 (5)	N1—C4—C5	108.2 (4)
O1—Cl1—O2	105.8 (5)	N1—C4—H4A	110.1
O1ii—Cl1—O2ii	105.8 (5)	C5—C4—H4A	110.1
O1—Cl1—O2ii	111.4 (5)	N1—C4—H4B	110.1
O2—Cl1—O2ii	115.3 (7)	C5—C4—H4B	110.1
C2—N1—C4	121.5 (4)	H4A—C4—H4B	108.4
C2—N1—Cu1	124.0 (4)	C4—C5—N2	105.8 (4)
C4—N1—Cu1	114.5 (3)	C4—C5—H5A	110.6
C6—N2—C5	118.9 (4)	N2—C5—H5A	110.6
C6—N2—Cu1	108.5 (3)	C4—C5—H5B	110.6
C5—N2—Cu1	107.2 (3)	N2—C5—H5B	110.6
C6—N2—H2	107.2	H5A—C5—H5B	108.7
C5—N2—H2	107.2	N2—C6—C6i	105.3 (4)
Cu1—N2—H2	107.2	N2—C6—H6A	110.7
C2—C1—C2i	129.7 (7)	C6i—C6—H6A	110.7
C2—C1—H1	115.1	N2—C6—H6B	110.7
C2i—C1—H1	115.1	C6i—C6—H6B	110.7
N1—C2—C1	121.3 (6)	H6A—C6—H6B	108.8
N1—C2—C3	118.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl1iii	0.91	2.81	3.668 (5)	157
N2—H2···O1i	0.91	2.02	2.917 (8)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ii	0.91	2.02	2.917 (8)	168

Symmetry codes: (i) ; (ii) .