Literature DB >> 21582376

Dichlorido{N-[1-(2-pyrid-yl)ethyl-idene]ethane-1,2-diamine}copper(II).

Qiang Wang, Cai-Feng Bi, Da-Qi Wang, Yu-Hua Fan.

Abstract

The title complex, [CuCl(2)(C(9)n class="Species">H(13)N(3))], is mononuclear and contains a five-coordinate Cu(II) atom. The geometry of the Cu(II) atom can be described as tetra-gonal-pyramidal derived from the calculation of the value τ = 0.102. The three N atoms of the pyridine and ethane-1,2-diamine ligands and one Cl atom belong to the basal plane and the other Cl atom represents the axial position of the pyramid. The Cu atom is displaced by 0.2599 (2) Å from the basal plane towards the axial Cl atom. In the crystal, mol-ecules are linked into chains by inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds.

Entities: Chemical Disease Species

Year: 2009 PMID： 21582376 PMCID： PMC2968900 DOI： 10.1107/S1600536809010149

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background, see: Coles et al. (1998 ▶). For the calculation of the geometry parameter τ in five-coordinate complexes, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[CuCl2(C9H13N3)] M = 297.66 Triclinic, a = 7.2701 (10) Å b = 8.8008 (12) Å c = 9.5773 (15) Å α = 82.940 (2)° β = 76.289 (1)° γ = 85.751 (2)° V = 590.16 (15) Å3 Z = 2 Mo Kα radiation μ = 2.27 mm−1 T = 298 K 0.50 × 0.42 × 0.17 mm

Data collection

Siemens SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.396, T max = 0.699 2903 measured reflections 2021 independent reflections 1549 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.160 S = 1.04 2021 reflections 136 parameters H-atom parameters constrained Δρmax = 0.91 e Å−3 Δρmin = −0.81 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536809010149/si2162sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010149/si2162Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CuCl₂(C₉H₁₃N₃)]	Z = 2
M_r = 297.66	F(000) = 302
Triclinic, P1	D_x = 1.675 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2701 (10) Å	Cell parameters from 1739 reflections
b = 8.8008 (12) Å	θ = 2.3–27.9°
c = 9.5773 (15) Å	µ = 2.27 mm⁻¹
α = 82.940 (2)°	T = 298 K
β = 76.289 (1)°	Block, green
γ = 85.751 (2)°	0.50 × 0.42 × 0.17 mm
V = 590.16 (15) Å³

Siemens SMART CCD area-detector diffractometer	2021 independent reflections
Radiation source: fine-focus sealed tube	1549 reflections with I > 2σ(I)
graphite	R_int = 0.034
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→8
T_min = 0.396, T_max = 0.699	k = −10→10
2903 measured reflections	l = −9→11

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) = 0.160	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0888P)² + 0.8983P] where P = (F_o² + 2F_c²)/3
2021 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.91 e Å⁻³
0 restraints	Δρ_min = −0.81 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	U_iso*/U_eq
Cu1	0.53050 (9)	0.78810 (8)	0.77470 (7)	0.0327 (3)
Cl1	0.7011 (2)	0.53529 (17)	0.80166 (16)	0.0397 (4)
Cl2	0.7438 (2)	0.9433 (2)	0.81435 (18)	0.0476 (4)
N1	0.6029 (6)	0.8157 (6)	0.5531 (5)	0.0341 (11)
N2	0.3090 (6)	0.7056 (6)	0.7282 (5)	0.0347 (11)
N3	0.3644 (7)	0.7751 (6)	0.9746 (5)	0.0357 (11)
H3A	0.4022	0.6933	1.0288	0.043*
H3B	0.3743	0.8597	1.0159	0.043*
C1	0.1667 (9)	0.6172 (9)	0.5489 (7)	0.0527 (18)
H1A	0.0658	0.5872	0.6302	0.079*
H1B	0.2225	0.5283	0.5032	0.079*
H1C	0.1171	0.6883	0.4809	0.079*
C2	0.3123 (8)	0.6909 (7)	0.5987 (6)	0.0343 (13)
C3	0.4844 (8)	0.7519 (7)	0.4929 (6)	0.0326 (13)
C4	0.5180 (9)	0.7429 (8)	0.3465 (6)	0.0427 (15)
H4	0.4342	0.6966	0.3070	0.051*
C5	0.6828 (10)	0.8058 (9)	0.2596 (7)	0.0561 (19)
H5	0.7108	0.8023	0.1601	0.067*
C6	0.8026 (10)	0.8725 (9)	0.3213 (7)	0.0531 (18)
H6	0.9125	0.9155	0.2646	0.064*
C7	0.7586 (9)	0.8752 (7)	0.4685 (7)	0.0416 (15)
H7	0.8408	0.9203	0.5105	0.050*
C8	0.1613 (8)	0.6561 (8)	0.8557 (6)	0.0412 (15)
H8A	0.1867	0.5504	0.8911	0.049*
H8B	0.0381	0.6645	0.8321	0.049*
C9	0.1656 (8)	0.7610 (8)	0.9685 (7)	0.0406 (14)
H9A	0.1095	0.8611	0.9436	0.049*
H9B	0.0931	0.7192	1.0622	0.049*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0302 (4)	0.0363 (5)	0.0324 (4)	−0.0047 (3)	−0.0096 (3)	0.0001 (3)
Cl1	0.0404 (8)	0.0339 (8)	0.0412 (8)	0.0017 (6)	−0.0079 (6)	0.0048 (6)
Cl2	0.0403 (9)	0.0487 (10)	0.0580 (10)	−0.0096 (7)	−0.0133 (7)	−0.0145 (8)
N1	0.031 (2)	0.035 (3)	0.033 (3)	−0.004 (2)	−0.007 (2)	0.007 (2)
N2	0.027 (2)	0.053 (3)	0.025 (2)	−0.009 (2)	−0.0086 (19)	0.002 (2)
N3	0.040 (3)	0.033 (3)	0.035 (3)	−0.001 (2)	−0.011 (2)	−0.001 (2)
C1	0.038 (3)	0.081 (5)	0.043 (4)	−0.016 (4)	−0.008 (3)	−0.015 (4)
C2	0.029 (3)	0.037 (3)	0.037 (3)	0.001 (2)	−0.012 (2)	0.001 (3)
C3	0.034 (3)	0.033 (3)	0.031 (3)	−0.002 (2)	−0.010 (2)	0.003 (2)
C4	0.042 (3)	0.051 (4)	0.036 (3)	−0.007 (3)	−0.013 (3)	0.001 (3)
C5	0.057 (4)	0.077 (5)	0.031 (3)	−0.009 (4)	−0.008 (3)	0.008 (3)
C6	0.044 (4)	0.060 (5)	0.047 (4)	−0.015 (3)	−0.003 (3)	0.015 (3)
C7	0.039 (3)	0.038 (3)	0.046 (4)	−0.009 (3)	−0.008 (3)	0.004 (3)
C8	0.033 (3)	0.053 (4)	0.037 (3)	−0.011 (3)	−0.007 (3)	0.001 (3)
C9	0.034 (3)	0.045 (4)	0.040 (3)	0.001 (3)	−0.006 (3)	−0.001 (3)

Cu1—N2	1.977 (5)	C1—H1C	0.9600
Cu1—N3	2.002 (5)	C2—C3	1.498 (8)
Cu1—N1	2.050 (5)	C3—C4	1.376 (8)
Cu1—Cl2	2.2659 (17)	C4—C5	1.396 (9)
Cu1—Cl1	2.4812 (16)	C4—H4	0.9300
N1—C7	1.327 (7)	C5—C6	1.363 (10)
N1—C3	1.333 (7)	C5—H5	0.9300
N2—C2	1.257 (7)	C6—C7	1.372 (9)
N2—C8	1.467 (7)	C6—H6	0.9300
N3—C9	1.475 (7)	C7—H7	0.9300
N3—H3A	0.9000	C8—C9	1.512 (9)
N3—H3B	0.9000	C8—H8A	0.9700
C1—C2	1.479 (8)	C8—H8B	0.9700
C1—H1A	0.9600	C9—H9A	0.9700
C1—H1B	0.9600	C9—H9B	0.9700

N2—Cu1—N3	82.95 (19)	N2—C2—C3	114.1 (5)
N2—Cu1—N1	78.71 (18)	C1—C2—C3	120.6 (5)
N3—Cu1—N1	158.54 (19)	N1—C3—C4	122.8 (5)
N2—Cu1—Cl2	164.66 (16)	N1—C3—C2	114.0 (5)
N3—Cu1—Cl2	96.66 (15)	C4—C3—C2	123.2 (5)
N1—Cu1—Cl2	98.10 (14)	C3—C4—C5	117.5 (6)
N2—Cu1—Cl1	95.01 (16)	C3—C4—H4	121.3
N3—Cu1—Cl1	96.91 (15)	C5—C4—H4	121.3
N1—Cu1—Cl1	95.69 (14)	C6—C5—C4	119.6 (6)
Cl2—Cu1—Cl1	100.26 (6)	C6—C5—H5	120.2
C7—N1—C3	118.8 (5)	C4—C5—H5	120.2
C7—N1—Cu1	127.4 (4)	C5—C6—C7	119.0 (6)
C3—N1—Cu1	113.5 (4)	C5—C6—H6	120.5
C2—N2—C8	126.8 (5)	C7—C6—H6	120.5
C2—N2—Cu1	119.1 (4)	N1—C7—C6	122.4 (6)
C8—N2—Cu1	113.9 (4)	N1—C7—H7	118.8
C9—N3—Cu1	109.9 (4)	C6—C7—H7	118.8
C9—N3—H3A	109.7	N2—C8—C9	106.3 (5)
Cu1—N3—H3A	109.7	N2—C8—H8A	110.5
C9—N3—H3B	109.7	C9—C8—H8A	110.5
Cu1—N3—H3B	109.7	N2—C8—H8B	110.5
H3A—N3—H3B	108.2	C9—C8—H8B	110.5
C2—C1—H1A	109.5	H8A—C8—H8B	108.7
C2—C1—H1B	109.5	N3—C9—C8	108.7 (5)
H1A—C1—H1B	109.5	N3—C9—H9A	109.9
C2—C1—H1C	109.5	C8—C9—H9A	109.9
H1A—C1—H1C	109.5	N3—C9—H9B	109.9
H1B—C1—H1C	109.5	C8—C9—H9B	109.9
N2—C2—C1	125.3 (5)	H9A—C9—H9B	108.3

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1ⁱ	0.90	2.47	3.248 (5)	145
N3—H3B···Cl2ⁱⁱ	0.90	2.49	3.322 (5)	154
C6—H6···Cl2ⁱⁱⁱ	0.93	2.77	3.666 (7)	161
C4—H4···Cl1^iv	0.93	2.74	3.612 (7)	156
C1—H1A···Cl1^v	0.96	2.80	3.726 (6)	161

Cu1—N2	1.977 (5)
Cu1—N3	2.002 (5)
Cu1—N1	2.050 (5)
Cu1—Cl2	2.2659 (17)
Cu1—Cl1	2.4812 (16)

N3—Cu1—N1	158.54 (19)
N2—Cu1—Cl2	164.66 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Cl1ⁱ	0.90	2.47	3.248 (5)	145
N3—H3B⋯Cl2ⁱⁱ	0.90	2.49	3.322 (5)	154
C6—H6⋯Cl2ⁱⁱⁱ	0.93	2.77	3.666 (7)	161
C4—H4⋯Cl1^iv	0.93	2.74	3.612 (7)	156
C1—H1A⋯Cl1^v	0.96	2.80	3.726 (6)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

1 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

1 in total

2 in total

1. Dichlorido{N,N-dimethyl-N'-[1-(2-pyrid-yl)ethyl-idene]ethane-1,2-diamine-κN,N',N''}copper(II).

Authors: Muhammad Saleh Salga; Hamid Khaledi; Hapipah Mohd Ali; Rustam Puteh
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-04-10

2. Dichlorido{2-(morpholin-4-yl)-N-[1-(pyridin-2-yl)ethyl-idene]ethanamine-κN,N',N''}copper(II) monohydrate.

Authors: Nura Suleiman Gwaram; Hamid Khaledi; Hapipah Mohd Ali
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-02-12

2 in total