Chlorido[N,N′-dibenzyl-N,N′-bis­(pyridin-2-ylmeth­yl)ethane-1,2-diamine]­copper(II) perchlorate methanol monosolvate

Song, H.-T.; Mao, J.-W.; Liu, M.; Pan, Z.-Q.

doi:10.1107/S1600536812017941

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m694-m695

doi:10.1107/S1600536812017941

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Chlorido[N,N′-dibenzyl-N,N′-bis(pyridin-2-ylmethyl)ethane-1,2-diamine]copper(II) perchlorate methanol monosolvate

Hui-Ting Song,^a Jia-Wei Mao,^b Ming Liu ^a and Zhi-Quan Pan ^a ^*

^aKey Laboratory for Green Chemical Process of the Ministry of Education, Wuhan Institute of Technology, Wuhan 430073, People's Republic of China, and ^bCollege of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, People's Republic of China
^*Correspondence e-mail: zhiqpan@163.com

(Received 19 April 2012; accepted 22 April 2012; online 28 April 2012)

In the title solvated molecular salt, [CuCl(C₂₈H₃₀N₄)]ClO₄·CH₃OH, the Cu²⁺ ion is coordinated by the N,N′,N′′,N′′′-tetradentate ligand and a chloride ion, generating a very distorted square-based pyramidal CuN₄Cl coordination geometry with the Cl⁻ ion in the basal position. In the crystal, the solvent molecules and anions are linked by weak O—H⋯O hydrogen bonding.

Related literature

For related copper complexes, see: Cejudo et al. (2006 ); Vaidyanathan & Nair (2003 ); Wang et al. (2007 ); Xiao et al. (2011 ). For further synthetic details, see: Hamid & Hamid (2010 ); Fenton et al. (1995 ); Sun et al. (2002 ). For geometric descriptors of five-coordinate metal ions, see: Addison et al. (1984 ).

Experimental

Crystal data

[CuCl(C₂₈H₃₀N₄)]ClO₄·CH₄O
M_r = 653.04
Monoclinic, P 2₁ /n
a = 17.800 (2) Å
b = 10.5804 (13) Å
c = 18.107 (2) Å
β = 118.374 (1)°
V = 3000.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 291 K
0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.777, T_max = 0.818
16310 measured reflections
5885 independent reflections
4329 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.110
S = 1.04
5885 reflections
372 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N3	1.983 (3)
Cu1—N2	2.022 (2)
Cu1—N4	2.087 (2)
Cu1—N1	2.152 (3)
Cu1—Cl2	2.2830 (9)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O12	0.96	2.48	3.140 (4)	126

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812017941/hb6747sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017941/hb6747Isup2.hkl

checkCIF report

Comment top

Recently, study of copper complex with polynitrogen ligands has been given considerable attention because of their interesting biochemical properties (Cejudo et al., 2006; Vaidyanathan et al., 2003; Wang et al., 2007; Xiao et al., 2011). In this paper, we report on the crystal structure of a new copper(II) complex with the polynitrogen ligand N¹,N²-dibenzyl-N¹,N²-bis(pyridin-2-ylmethyl)ethane-1,2-diamine (L).

The structure of the title compound is shown in Fig.1. The Cu(II) atom is five-coordinated by two amino N atoms and two pyridine N atoms from the ligand L and one Cl atom. The coordination geometry for central Cu(II) atom can be described as distorted square based pyramidal, with τ = 0.30 (Addison et al., 1984).

Related literature top

For related copper complexes, see: Cejudo et al. (2006); Vaidyanathan et al. (2003); Wang et al. (2007); Xiao et al. (2011). For further synthetic details, see: Hamid & Hamid (2010); Fenton et al. (1995); Sun et al. (2002). For geometric descriptors of five-coordinate metal ions, see: Addison et al. (1984).

Experimental top

N,N'-bis(2-benzylmethyl)-1,2-diaminoethane was prepared using a variant of the method suggested by Hamid & Hamid (2010). The ligand L was synthesized according to a procedure reported previously (Fenton et al. 1995; Sun et al., 2002). To a refluxing solution of L (0.149 g, 0.3 mmol) in absolute methanol (15 ml) was added dropwise a solution of CuCl₂ (0.0404 g 0.3 mmol)and Cu(ClO₄)₂.6H₂O (0.112 g, 0.3 mmol). After the addition was completed, the resulting solution became green, and the mixture was stirred for about 6 h at room temperature. After filtration, blue blocks were obtained by slow evaporation of the absolute methanol solution at room temperature for two weeks.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

Chlorido[N,N'-dibenzyl-N,N'-bis(pyridin-2- ylmethyl)ethane-1,2-diamine]copper(II) perchlorate methanol monosolvate top

Crystal data top

[CuCl(C₂₈H₃₀N₄)]ClO₄·CH₄O	F(000) = 1356
M_r = 653.04	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4897 reflections
a = 17.800 (2) Å	θ = 2.2–24.4°
b = 10.5804 (13) Å	µ = 0.95 mm⁻¹
c = 18.107 (2) Å	T = 291 K
β = 118.374 (1)°	Block, blue
V = 3000.3 (6) Å³	0.28 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	5885 independent reflections
Radiation source: sealed tube	4329 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
phi and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −21→21
T_min = 0.777, T_max = 0.818	k = −13→12
16310 measured reflections	l = −22→15

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.05P)² + 1.22P] where P = (F_o² + 2F_c²)/3
5885 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[CuCl(C₂₈H₃₀N₄)]ClO₄·CH₄O	V = 3000.3 (6) Å³
M_r = 653.04	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.800 (2) Å	µ = 0.95 mm⁻¹
b = 10.5804 (13) Å	T = 291 K
c = 18.107 (2) Å	0.28 × 0.24 × 0.22 mm
β = 118.374 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	5885 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4329 reflections with I > 2σ(I)
T_min = 0.777, T_max = 0.818	R_int = 0.042
16310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.04	Δρ_max = 0.24 e Å⁻³
5885 reflections	Δρ_min = −0.36 e Å⁻³
372 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.8517 (2)	−0.0164 (3)	0.6532 (2)	0.0510 (8)
H1	0.8516	−0.0832	0.6199	0.061*
C2	0.8816 (2)	−0.0377 (3)	0.7372 (2)	0.0506 (8)
H2	0.9009	−0.1173	0.7601	0.061*
C3	0.8824 (2)	0.0609 (4)	0.7866 (2)	0.0529 (9)
H3	0.9028	0.0492	0.8439	0.064*
C4	0.8530 (2)	0.1772 (3)	0.7508 (2)	0.0476 (8)
H4	0.8530	0.2451	0.7834	0.057*
C5	0.82358 (18)	0.1917 (3)	0.66583 (18)	0.0356 (6)
C6	0.7922 (2)	0.3167 (3)	0.62251 (18)	0.0400 (7)
H6A	0.7611	0.3600	0.6469	0.048*
H6B	0.8408	0.3688	0.6318	0.048*
C7	0.72963 (18)	0.4225 (3)	0.48671 (18)	0.0364 (6)
H7A	0.6993	0.4058	0.4269	0.044*
H7B	0.7869	0.4491	0.5004	0.044*
C8	0.68568 (18)	0.5318 (3)	0.50492 (18)	0.0360 (6)
C9	0.7309 (2)	0.6120 (3)	0.5716 (2)	0.0436 (7)
H9	0.7882	0.5960	0.6083	0.052*
C10	0.6910 (2)	0.7169 (3)	0.5842 (2)	0.0499 (8)
H10	0.7217	0.7699	0.6298	0.060*
C11	0.6071 (2)	0.7426 (3)	0.5301 (2)	0.0515 (8)
H11	0.5811	0.8134	0.5384	0.062*
C12	0.5617 (2)	0.6636 (3)	0.4638 (2)	0.0542 (9)
H12	0.5045	0.6803	0.4274	0.065*
C13	0.6003 (2)	0.5599 (3)	0.4508 (2)	0.0441 (7)
H13	0.5689	0.5074	0.4051	0.053*
C14	0.8694 (2)	−0.0635 (3)	0.4603 (2)	0.0523 (8)
H14	0.9185	−0.0147	0.4794	0.063*
C15	0.8721 (2)	−0.1880 (4)	0.4398 (2)	0.0550 (9)
H15	0.9223	−0.2235	0.4451	0.066*
C16	0.7996 (2)	−0.2578 (4)	0.4116 (2)	0.0547 (9)
H16	0.8000	−0.3424	0.3979	0.066*
C17	0.7244 (2)	−0.2037 (3)	0.4031 (2)	0.0512 (8)
H17	0.6743	−0.2506	0.3824	0.061*
C18	0.7261 (2)	−0.0808 (3)	0.4257 (2)	0.0440 (7)
C19	0.65156 (19)	−0.0122 (3)	0.4241 (2)	0.0420 (7)
H19A	0.5985	−0.0494	0.3823	0.050*
H19B	0.6534	−0.0185	0.4784	0.050*
C20	0.6269 (2)	0.1318 (3)	0.31094 (19)	0.0419 (7)
H20A	0.6577	0.0699	0.2961	0.050*
H20B	0.5667	0.1106	0.2805	0.050*
C21	0.63972 (19)	0.2601 (3)	0.28309 (18)	0.0420 (7)
C22	0.5718 (2)	0.3417 (4)	0.2408 (2)	0.0567 (9)
H22	0.5167	0.3152	0.2263	0.068*
C23	0.5853 (2)	0.4638 (4)	0.2196 (2)	0.0579 (9)
H23	0.5395	0.5188	0.1921	0.070*
C24	0.6649 (3)	0.5012 (4)	0.2394 (2)	0.0601 (10)
H24	0.6740	0.5822	0.2254	0.072*
C25	0.7326 (2)	0.4209 (4)	0.2799 (2)	0.0561 (9)
H25	0.7873	0.4473	0.2927	0.067*
C26	0.7200 (2)	0.3020 (4)	0.3015 (2)	0.0498 (8)
H26	0.7665	0.2484	0.3293	0.060*
C27	0.65133 (19)	0.2506 (3)	0.51552 (19)	0.0402 (7)
H27A	0.6191	0.3162	0.5254	0.048*
H27B	0.6598	0.1815	0.5539	0.048*
C28	0.60207 (18)	0.2044 (3)	0.4264 (2)	0.0414 (7)
H28A	0.5526	0.1569	0.4199	0.050*
H28B	0.5819	0.2763	0.3887	0.050*
C29	0.5166 (3)	0.8830 (4)	0.1346 (3)	0.0703 (11)
H29A	0.4710	0.9427	0.1070	0.105*
H29B	0.5199	0.8293	0.0935	0.105*
H29C	0.5695	0.9276	0.1652	0.105*
Cl1	0.39157 (5)	0.94576 (7)	0.32224 (5)	0.04209 (18)
Cl2	0.90470 (5)	0.25490 (9)	0.50649 (6)	0.0526 (2)
Cu1	0.78296 (2)	0.15945 (3)	0.49085 (2)	0.03736 (12)
N1	0.82264 (17)	0.0959 (2)	0.61692 (16)	0.0436 (6)
N2	0.73604 (15)	0.3018 (2)	0.53140 (15)	0.0349 (5)
N3	0.79833 (15)	−0.0104 (2)	0.45376 (16)	0.0407 (6)
N4	0.65620 (15)	0.1222 (2)	0.40350 (15)	0.0362 (5)
O1	0.50092 (17)	0.8086 (3)	0.19076 (18)	0.0680 (7)
H1B	0.5193	0.8540	0.2424	0.082*
O11	0.44953 (15)	0.9508 (2)	0.40876 (14)	0.0556 (6)
O12	0.43016 (16)	0.9986 (3)	0.27602 (17)	0.0634 (7)
O13	0.36408 (16)	0.8190 (2)	0.30031 (17)	0.0628 (7)
O14	0.31790 (16)	1.0195 (3)	0.30381 (17)	0.0639 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0486 (18)	0.0393 (18)	0.0505 (19)	0.0061 (15)	0.0116 (16)	0.0060 (15)
C2	0.0488 (18)	0.0376 (18)	0.0486 (19)	0.0091 (14)	0.0095 (15)	0.0165 (15)
C3	0.0494 (19)	0.061 (2)	0.0385 (17)	0.0044 (17)	0.0126 (15)	0.0105 (16)
C4	0.0482 (18)	0.0468 (19)	0.0387 (17)	0.0063 (15)	0.0134 (15)	0.0055 (14)
C5	0.0362 (15)	0.0360 (16)	0.0380 (15)	0.0020 (12)	0.0203 (13)	0.0036 (12)
C6	0.0468 (17)	0.0354 (17)	0.0341 (15)	0.0025 (13)	0.0163 (13)	0.0003 (12)
C7	0.0338 (14)	0.0349 (16)	0.0345 (15)	−0.0009 (12)	0.0114 (12)	0.0020 (12)
C8	0.0361 (14)	0.0320 (15)	0.0336 (15)	0.0005 (12)	0.0114 (12)	0.0059 (12)
C9	0.0452 (17)	0.0414 (17)	0.0375 (16)	−0.0043 (14)	0.0144 (14)	0.0005 (13)
C10	0.055 (2)	0.0382 (18)	0.0450 (18)	−0.0043 (15)	0.0140 (16)	−0.0050 (15)
C11	0.057 (2)	0.0370 (18)	0.0508 (19)	0.0074 (15)	0.0175 (17)	0.0027 (15)
C12	0.0476 (19)	0.0454 (19)	0.053 (2)	0.0141 (16)	0.0103 (16)	0.0078 (16)
C13	0.0472 (17)	0.0385 (17)	0.0379 (16)	−0.0009 (14)	0.0132 (14)	−0.0007 (13)
C14	0.0478 (18)	0.0432 (19)	0.054 (2)	0.0122 (15)	0.0150 (16)	−0.0007 (15)
C15	0.0447 (18)	0.056 (2)	0.055 (2)	0.0162 (16)	0.0160 (16)	0.0022 (17)
C16	0.054 (2)	0.0446 (19)	0.053 (2)	0.0180 (16)	0.0161 (17)	0.0082 (16)
C17	0.0456 (18)	0.0356 (17)	0.060 (2)	0.0038 (14)	0.0153 (16)	0.0067 (15)
C18	0.0410 (16)	0.0374 (17)	0.0469 (18)	0.0051 (13)	0.0154 (14)	0.0054 (14)
C19	0.0388 (16)	0.0300 (15)	0.0464 (18)	−0.0062 (12)	0.0115 (14)	−0.0010 (13)
C20	0.0447 (17)	0.0391 (17)	0.0400 (16)	−0.0047 (13)	0.0186 (14)	−0.0091 (13)
C21	0.0381 (15)	0.0504 (19)	0.0300 (15)	0.0026 (14)	0.0100 (13)	−0.0046 (13)
C22	0.0435 (18)	0.061 (2)	0.052 (2)	0.0088 (16)	0.0112 (16)	0.0169 (18)
C23	0.059 (2)	0.055 (2)	0.051 (2)	0.0086 (18)	0.0198 (18)	0.0135 (17)
C24	0.066 (2)	0.052 (2)	0.052 (2)	−0.0044 (18)	0.0199 (18)	0.0146 (17)
C25	0.052 (2)	0.053 (2)	0.053 (2)	−0.0111 (16)	0.0163 (17)	0.0013 (17)
C26	0.0442 (18)	0.056 (2)	0.0389 (17)	0.0007 (15)	0.0112 (14)	−0.0035 (15)
C27	0.0394 (16)	0.0392 (16)	0.0386 (16)	0.0036 (13)	0.0156 (13)	0.0075 (13)
C28	0.0287 (14)	0.0338 (16)	0.0509 (19)	−0.0001 (12)	0.0101 (13)	−0.0057 (13)
C29	0.073 (3)	0.061 (3)	0.063 (3)	−0.013 (2)	0.021 (2)	−0.010 (2)
Cl1	0.0397 (4)	0.0399 (4)	0.0418 (4)	0.0014 (3)	0.0154 (3)	0.0004 (3)
Cl2	0.0352 (4)	0.0541 (5)	0.0591 (5)	−0.0073 (3)	0.0146 (4)	0.0039 (4)
Cu1	0.03061 (19)	0.0358 (2)	0.0403 (2)	−0.00030 (15)	0.01249 (15)	−0.00317 (16)
N1	0.0446 (14)	0.0358 (14)	0.0408 (14)	0.0050 (11)	0.0126 (12)	0.0044 (11)
N2	0.0360 (12)	0.0325 (13)	0.0308 (12)	−0.0019 (10)	0.0114 (10)	−0.0002 (10)
N3	0.0369 (13)	0.0390 (14)	0.0406 (14)	0.0019 (11)	0.0139 (11)	−0.0011 (11)
N4	0.0318 (12)	0.0310 (12)	0.0402 (13)	−0.0034 (10)	0.0126 (11)	−0.0011 (10)
O1	0.0582 (15)	0.0594 (16)	0.0646 (16)	0.0164 (13)	0.0113 (13)	0.0211 (14)
O11	0.0487 (13)	0.0586 (15)	0.0453 (13)	−0.0095 (11)	0.0109 (11)	−0.0012 (11)
O12	0.0546 (14)	0.0589 (16)	0.0616 (16)	0.0028 (12)	0.0153 (13)	0.0166 (13)
O13	0.0516 (14)	0.0526 (15)	0.0672 (16)	−0.0052 (11)	0.0145 (13)	−0.0131 (13)
O14	0.0539 (14)	0.0623 (17)	0.0607 (16)	0.0141 (13)	0.0151 (13)	0.0054 (13)

Geometric parameters (Å, º) top

C1—N1	1.337 (4)	C19—N4	1.483 (4)
C1—C2	1.369 (5)	C19—H19A	0.9700
C1—H1	0.9300	C19—H19B	0.9700
C2—C3	1.370 (5)	C20—C21	1.502 (5)
C2—H2	0.9300	C20—N4	1.504 (4)
C3—C4	1.373 (5)	C20—H20A	0.9700
C3—H3	0.9300	C20—H20B	0.9700
C4—C5	1.378 (4)	C21—C26	1.377 (5)
C4—H4	0.9300	C21—C22	1.383 (5)
C5—N1	1.340 (4)	C22—C23	1.400 (5)
C5—C6	1.504 (4)	C22—H22	0.9300
C6—N2	1.476 (4)	C23—C24	1.347 (5)
C6—H6A	0.9700	C23—H23	0.9300
C6—H6B	0.9700	C24—C25	1.367 (5)
C7—N2	1.486 (4)	C24—H24	0.9300
C7—C8	1.518 (4)	C25—C26	1.368 (5)
C7—H7A	0.9700	C25—H25	0.9300
C7—H7B	0.9700	C26—H26	0.9300
C8—C9	1.379 (4)	C27—N2	1.496 (4)
C8—C13	1.394 (4)	C27—C28	1.505 (4)
C9—C10	1.393 (5)	C27—H27A	0.9700
C9—H9	0.9300	C27—H27B	0.9700
C10—C11	1.368 (5)	C28—N4	1.496 (4)
C10—H10	0.9300	C28—H28A	0.9700
C11—C12	1.367 (5)	C28—H28B	0.9700
C11—H11	0.9300	C29—O1	1.414 (5)
C12—C13	1.373 (5)	C29—H29A	0.9600
C12—H12	0.9300	C29—H29B	0.9600
C13—H13	0.9300	C29—H29C	0.9600
C14—N3	1.336 (4)	Cl1—O11	1.409 (2)
C14—C15	1.376 (5)	Cl1—O13	1.419 (3)
C14—H14	0.9300	Cl1—O14	1.423 (3)
C15—C16	1.359 (5)	Cl1—O12	1.425 (3)
C15—H15	0.9300	Cu1—N3	1.983 (3)
C16—C17	1.394 (5)	Cu1—N2	2.022 (2)
C16—H16	0.9300	Cu1—N4	2.087 (2)
C17—C18	1.359 (5)	Cu1—N1	2.152 (3)
C17—H17	0.9300	Cu1—Cl2	2.2830 (9)
C18—N3	1.359 (4)	O1—H1B	0.9600
C18—C19	1.500 (4)

N1—C1—C2	123.2 (3)	C26—C21—C22	117.8 (3)
N1—C1—H1	118.4	C26—C21—C20	121.0 (3)
C2—C1—H1	118.4	C22—C21—C20	121.2 (3)
C1—C2—C3	118.5 (3)	C21—C22—C23	120.6 (3)
C1—C2—H2	120.7	C21—C22—H22	119.7
C3—C2—H2	120.7	C23—C22—H22	119.7
C2—C3—C4	119.4 (3)	C24—C23—C22	119.6 (3)
C2—C3—H3	120.3	C24—C23—H23	120.2
C4—C3—H3	120.3	C22—C23—H23	120.2
C3—C4—C5	118.9 (3)	C23—C24—C25	120.6 (4)
C3—C4—H4	120.5	C23—C24—H24	119.7
C5—C4—H4	120.5	C25—C24—H24	119.7
N1—C5—C4	122.2 (3)	C24—C25—C26	120.1 (3)
N1—C5—C6	115.8 (3)	C24—C25—H25	119.9
C4—C5—C6	122.0 (3)	C26—C25—H25	119.9
N2—C6—C5	112.0 (2)	C25—C26—C21	121.3 (3)
N2—C6—H6A	109.2	C25—C26—H26	119.3
C5—C6—H6A	109.2	C21—C26—H26	119.3
N2—C6—H6B	109.2	N2—C27—C28	110.1 (2)
C5—C6—H6B	109.2	N2—C27—H27A	109.6
H6A—C6—H6B	107.9	C28—C27—H27A	109.6
N2—C7—C8	116.8 (2)	N2—C27—H27B	109.6
N2—C7—H7A	108.1	C28—C27—H27B	109.6
C8—C7—H7A	108.1	H27A—C27—H27B	108.1
N2—C7—H7B	108.1	N4—C28—C27	111.2 (2)
C8—C7—H7B	108.1	N4—C28—H28A	109.4
H7A—C7—H7B	107.3	C27—C28—H28A	109.4
C9—C8—C13	118.2 (3)	N4—C28—H28B	109.4
C9—C8—C7	120.8 (3)	C27—C28—H28B	109.4
C13—C8—C7	120.8 (3)	H28A—C28—H28B	108.0
C8—C9—C10	120.2 (3)	O1—C29—H29A	109.5
C8—C9—H9	119.9	O1—C29—H29B	109.5
C10—C9—H9	119.9	H29A—C29—H29B	109.5
C11—C10—C9	120.6 (3)	O1—C29—H29C	109.5
C11—C10—H10	119.7	H29A—C29—H29C	109.5
C9—C10—H10	119.7	H29B—C29—H29C	109.5
C12—C11—C10	119.7 (3)	O11—Cl1—O13	108.66 (16)
C12—C11—H11	120.2	O11—Cl1—O14	110.26 (16)
C10—C11—H11	120.2	O13—Cl1—O14	107.23 (17)
C11—C12—C13	120.3 (3)	O11—Cl1—O12	109.60 (15)
C11—C12—H12	119.9	O13—Cl1—O12	113.89 (17)
C13—C12—H12	119.9	O14—Cl1—O12	107.14 (16)
C12—C13—C8	121.1 (3)	N3—Cu1—N2	161.01 (10)
C12—C13—H13	119.4	N3—Cu1—N4	81.13 (10)
C8—C13—H13	119.4	N2—Cu1—N4	86.06 (10)
N3—C14—C15	122.1 (3)	N3—Cu1—N1	92.73 (10)
N3—C14—H14	118.9	N2—Cu1—N1	80.29 (10)
C15—C14—H14	118.9	N4—Cu1—N1	115.89 (10)
C16—C15—C14	118.1 (3)	N3—Cu1—Cl2	99.64 (8)
C16—C15—H15	120.9	N2—Cu1—Cl2	99.03 (7)
C14—C15—H15	120.9	N4—Cu1—Cl2	142.95 (7)
C15—C16—C17	120.6 (3)	N1—Cu1—Cl2	101.12 (8)
C15—C16—H16	119.7	C1—N1—C5	117.8 (3)
C17—C16—H16	119.7	C1—N1—Cu1	130.9 (2)
C18—C17—C16	118.5 (3)	C5—N1—Cu1	111.08 (19)
C18—C17—H17	120.7	C6—N2—C7	110.6 (2)
C16—C17—H17	120.7	C6—N2—C27	109.8 (2)
N3—C18—C17	121.2 (3)	C7—N2—C27	113.4 (2)
N3—C18—C19	114.4 (3)	C6—N2—Cu1	107.97 (18)
C17—C18—C19	124.4 (3)	C7—N2—Cu1	112.35 (17)
N4—C19—C18	108.3 (3)	C27—N2—Cu1	102.29 (18)
N4—C19—H19A	110.0	C14—N3—C18	119.4 (3)
C18—C19—H19A	110.0	C14—N3—Cu1	128.9 (2)
N4—C19—H19B	110.0	C18—N3—Cu1	111.4 (2)
C18—C19—H19B	110.0	C19—N4—C28	111.5 (2)
H19A—C19—H19B	108.4	C19—N4—C20	108.3 (2)
C21—C20—N4	114.1 (2)	C28—N4—C20	110.0 (2)
C21—C20—H20A	108.7	C19—N4—Cu1	99.18 (17)
N4—C20—H20A	108.7	C28—N4—Cu1	106.68 (17)
C21—C20—H20B	108.7	C20—N4—Cu1	120.60 (18)
N4—C20—H20B	108.7	C29—O1—H1B	109.3
H20A—C20—H20B	107.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O12	0.96	2.48	3.140 (4)	126

Experimental details

Crystal data
Chemical formula	[CuCl(C₂₈H₃₀N₄)]ClO₄·CH₄O
M_r	653.04
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	17.800 (2), 10.5804 (13), 18.107 (2)
β (°)	118.374 (1)
V (Å³)	3000.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.28 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.777, 0.818
No. of measured, independent and observed [I > 2σ(I)] reflections	16310, 5885, 4329
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.110, 1.04
No. of reflections	5885
No. of parameters	372
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.36

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—N3	1.983 (3)	Cu1—N1	2.152 (3)
Cu1—N2	2.022 (2)	Cu1—Cl2	2.2830 (9)
Cu1—N4	2.087 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O12	0.96	2.48	3.140 (4)	126

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (20971102) and the Foundation for Midlife and Youth Talent project of Hubei Province, China (Q20111507).

References

Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349-1356. CSD CrossRef Web of Science Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS inc., Madison, Wisconsin, USA. Google Scholar
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Hamid, G. & Hamid, R. M. (2010). Bull. Chem. Soc. Ethiop. 24, 151–155. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 68| Part 5| May 2012| Pages m694-m695

doi:10.1107/S1600536812017941

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Chlorido[N,N′-di­benzyl-N,N′-bis­­(pyridin-2-ylmeth­yl)ethane-1,2-di­amine]­copper(II) perchlorate methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Chlorido[N,N′-dibenzyl-N,N′-bis(pyridin-2-ylmethyl)ethane-1,2-diamine]copper(II) perchlorate methanol monosolvate