[2-(Dimethyl-amino)-ethanol-κ(2)N,O][2-(dimethyl-amino)-ethano-lato-κ(2)N,O]iodidocopper(II).

The title compound, [Cu(C(4)H(10)NO)I(C(4)H(11)NO)], was obtained unintentionally as the product of an attempted synthesis of a Cu/Zn mixed-metal complex using zerovalent copper, zinc(II) oxide and ammonium iodide in pure 2-(dimethyl-amino)-ethanol, in air. The mol-ecular complex has no crystallographically imposed symmetry. The coordination geometry around the metal atom is distorted square-pyramidal. The equatorial coordination around copper involves donor atoms of the bidentate chelating 2-(dimethyl-amino)-ethanol ligand and the 2-(dimethyl-amino)-ethano-late group, which are mutually trans to each other, with four approximately equal short Cu-O/N bond distances. The axial Cu-I bond is substanti-ally elongated. Inter-molecular hydrogen-bonding inter-actions involving the -OH group of the neutral 2-(dimethyl-amino)-ethanol ligand to the O atom of the monodeprotonated 2-(dimethyl-amino)-ethano-late group of the mol-ecule related by the n-glide plane, as indicated by the O⋯O distance of 2.482 (12) Å, form chains of mol-ecules propagating along [101].

Related literature

For background to the synthesis, see: Vinogradova et al. (2002 ▶). Buvaylo et al. (2009 ▶, 2011 ▶). Elongation of the axial Cu—I bond is common in this kind of compound, see: Wells (1986 ▶).

Experimental

Crystal data

[Cu(C4H10NO)I(C4H11NO)]

M = 367.71

Monoclinic,

a = 8.690 (1) Å

b = 15.241 (1) Å

c = 11.116 (1) Å

β = 106.847 (10)°

V = 1409.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.72 mm−1

T = 296 K

0.32 × 0.3 × 0.2 mm

Data collection

Rigaku AFC-6S diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.333, T max = 0.47

2642 measured reflections

2471 independent reflections

1003 reflections with I > 2σ(I)

R int = 0.089

3 standard reflections every 150 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.204

S = 1.00

2471 reflections

133 parameters

H-atom parameters constrained

Δρmax = 1.80 e Å−3

Δρmin = −0.83 e Å−3

Data collection: AFC6S Diffractometer Control Software (Molecular Structure Corporation, 1998) ▶; cell refinement: AFC6S Diffractometer Control Software; data reduction: TEXSAN (Molec­ular Structure Corporation & Rigaku, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Johnson (1976 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010215/ds2178sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010215/ds2178Isup2.hkl

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

[Cu(C4H10NO)I(C4H11NO)]	F(000) = 724
Mr = 367.71	Dx = 1.733 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -p 2yn	Cell parameters from 6 reflections
a = 8.690 (1) Å	θ = 10.9–11.9°
b = 15.241 (1) Å	µ = 3.72 mm−1
c = 11.116 (1) Å	T = 296 K
β = 106.847 (10)°	Rod, blue-green
V = 1409.1 (2) Å3	0.32 × 0.3 × 0.2 mm
Z = 4

Rigaku AFC-6S diffractometer	1003 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
Graphite monochromator	θmax = 25°, θmin = 2.3°
2θ–ω scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
Tmin = 0.333, Tmax = 0.47	l = −13→12
2642 measured reflections	3 standard reflections every 150 reflections
2471 independent reflections	intensity decay: none

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0962P)2] where P = (Fo2 + 2Fc2)/3
2471 reflections	(Δ/σ)max = 0.013
133 parameters	Δρmax = 1.80 e Å−3
0 restraints	Δρmin = −0.83 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
I1	0.64794 (15)	0.39539 (8)	0.25072 (11)	0.0679 (5)
Cu1	0.4723 (2)	0.26167 (12)	0.34694 (15)	0.0456 (6)
O1	0.5633 (10)	0.2803 (6)	0.5351 (8)	0.044 (2)
O2	0.3381 (11)	0.2106 (6)	0.1834 (8)	0.038 (2)
H2O	0.2428	0.2147	0.1437	0.08 (6)*
N1	0.2813 (13)	0.3302 (7)	0.3748 (9)	0.038 (3)
N2	0.6101 (12)	0.1521 (7)	0.3455 (9)	0.033 (3)
C1	0.4697 (16)	0.3364 (10)	0.5848 (13)	0.050 (4)
H1A	0.5391	0.3755	0.6457	0.06*
H1B	0.4074	0.3021	0.6276	0.06*
C2	0.3579 (18)	0.3894 (9)	0.4808 (13)	0.048 (4)
H2A	0.2761	0.4173	0.5113	0.057*
H2B	0.4178	0.4349	0.453	0.057*
C3	0.1879 (19)	0.3814 (10)	0.2666 (13)	0.061 (5)
H3A	0.0986	0.4086	0.2864	0.092*
H3B	0.1488	0.3434	0.1954	0.092*
H3C	0.2551	0.4259	0.247	0.092*
C4	0.1717 (17)	0.2652 (10)	0.4069 (14)	0.052 (4)
H4A	0.0854	0.2955	0.427	0.079*
H4B	0.2304	0.2311	0.4781	0.079*
H4C	0.1284	0.2271	0.3365	0.079*
C5	0.4044 (16)	0.1367 (9)	0.1424 (13)	0.046 (4)
H5A	0.3869	0.1398	0.0523	0.055*
H5B	0.3528	0.0839	0.1607	0.055*
C6	0.5814 (15)	0.1335 (9)	0.2087 (11)	0.038 (3)
H6A	0.6234	0.0759	0.198	0.045*
H6B	0.637	0.1766	0.1725	0.045*
C7	0.7829 (17)	0.1630 (11)	0.4054 (13)	0.059 (5)
H7A	0.8063	0.1534	0.4942	0.089*
H7B	0.8144	0.2215	0.3905	0.089*
H7C	0.8413	0.1214	0.3707	0.089*
C8	0.5534 (19)	0.0790 (9)	0.4089 (13)	0.054 (4)
H8A	0.5948	0.0246	0.3877	0.08*
H8B	0.4381	0.0775	0.382	0.08*
H8C	0.5906	0.0876	0.4982	0.08*

	U11	U22	U33	U12	U13	U23
I1	0.0801 (9)	0.0630 (7)	0.0579 (7)	−0.0279 (7)	0.0159 (6)	0.0090 (6)
Cu1	0.0337 (9)	0.0659 (13)	0.0304 (9)	0.0154 (9)	−0.0015 (7)	−0.0125 (9)
O1	0.040 (5)	0.057 (6)	0.032 (5)	0.016 (5)	0.006 (4)	−0.003 (5)
O2	0.030 (6)	0.046 (6)	0.034 (5)	−0.003 (4)	0.004 (4)	−0.012 (5)
N1	0.042 (7)	0.047 (7)	0.021 (6)	0.013 (5)	0.005 (5)	−0.001 (5)
N2	0.033 (6)	0.045 (7)	0.020 (5)	−0.010 (5)	0.005 (5)	−0.001 (5)
C1	0.038 (9)	0.063 (11)	0.046 (9)	0.004 (8)	0.005 (7)	−0.006 (8)
C2	0.050 (9)	0.046 (9)	0.045 (8)	0.003 (8)	0.010 (7)	−0.015 (8)
C3	0.073 (12)	0.062 (11)	0.037 (8)	0.027 (9)	−0.001 (8)	−0.001 (8)
C4	0.048 (9)	0.070 (11)	0.053 (9)	−0.019 (8)	0.035 (8)	−0.008 (8)
C5	0.053 (9)	0.048 (9)	0.032 (8)	0.011 (7)	0.007 (7)	0.005 (7)
C6	0.038 (8)	0.045 (9)	0.030 (7)	0.011 (7)	0.011 (6)	0.014 (6)
C7	0.059 (10)	0.071 (12)	0.042 (9)	0.033 (9)	0.008 (8)	−0.009 (9)
C8	0.081 (12)	0.043 (9)	0.034 (8)	0.000 (8)	0.013 (8)	0.011 (7)

I1—Cu1	2.928 (2)	C2—H2B	0.97
Cu1—O1	2.030 (9)	C3—H3A	0.96
Cu1—N2	2.058 (11)	C3—H3B	0.96
Cu1—N1	2.059 (10)	C3—H3C	0.96
Cu1—O2	2.010 (8)	C4—H4A	0.96
O1—C1	1.399 (16)	C4—H4B	0.96
O2—C5	1.400 (16)	C4—H4C	0.96
O2—H2O	0.82	C5—C6	1.502 (17)
N1—C3	1.466 (15)	C5—H5A	0.97
N1—C2	1.481 (16)	C5—H5B	0.97
N1—C4	1.488 (16)	C6—H6A	0.97
N2—C7	1.465 (16)	C6—H6B	0.97
N2—C8	1.476 (17)	C7—H7A	0.96
N2—C6	1.495 (15)	C7—H7B	0.96
C1—C2	1.512 (19)	C7—H7C	0.96
C1—H1A	0.97	C8—H8A	0.96
C1—H1B	0.97	C8—H8B	0.96
C2—H2A	0.97	C8—H8C	0.96
O1—Cu1—N2	93.9 (4)	N1—C3—H3A	109.5
O1—Cu1—N1	82.2 (4)	N1—C3—H3B	109.5
N2—Cu1—N1	155.4 (4)	H3A—C3—H3B	109.5
O1—Cu1—I1	101.0 (3)	N1—C3—H3C	109.5
N2—Cu1—I1	101.3 (3)	H3A—C3—H3C	109.5
N1—Cu1—I1	103.3 (3)	H3B—C3—H3C	109.5
I1—Cu1—O2	99.6 (3)	N1—C4—H4A	109.5
O1—Cu1—O2	159.5 (4)	N1—C4—H4B	109.5
O2—Cu1—N1	92.9 (4)	H4A—C4—H4B	109.5
O2—Cu1—N2	82.3 (4)	N1—C4—H4C	109.5
C1—O1—Cu1	113.3 (7)	H4A—C4—H4C	109.5
C5—O2—H2O	109.5	H4B—C4—H4C	109.5
C3—N1—C2	110.0 (11)	O2—C5—C6	109.0 (11)
C3—N1—C4	108.1 (11)	O2—C5—H5A	109.9
C2—N1—C4	112.7 (11)	C6—C5—H5A	109.9
C3—N1—Cu1	115.2 (9)	O2—C5—H5B	109.9
C2—N1—Cu1	103.5 (8)	C6—C5—H5B	109.9
C4—N1—Cu1	107.4 (8)	H5A—C5—H5B	108.3
C7—N2—C8	108.0 (11)	N2—C6—C5	109.7 (10)
C7—N2—C6	109.3 (10)	N2—C6—H6A	109.7
C8—N2—C6	111.3 (10)	C5—C6—H6A	109.7
C7—N2—Cu1	115.2 (9)	N2—C6—H6B	109.7
C8—N2—Cu1	109.4 (8)	C5—C6—H6B	109.7
C6—N2—Cu1	103.6 (7)	H6A—C6—H6B	108.2
O1—C1—C2	110.1 (11)	N2—C7—H7A	109.5
O1—C1—H1A	109.6	N2—C7—H7B	109.5
C2—C1—H1A	109.6	H7A—C7—H7B	109.5
O1—C1—H1B	109.6	N2—C7—H7C	109.5
C2—C1—H1B	109.6	H7A—C7—H7C	109.5
H1A—C1—H1B	108.2	H7B—C7—H7C	109.5
N1—C2—C1	108.9 (11)	N2—C8—H8A	109.5
N1—C2—H2A	109.9	N2—C8—H8B	109.5
C1—C2—H2A	109.9	H8A—C8—H8B	109.5
N1—C2—H2B	109.9	N2—C8—H8C	109.5
C1—C2—H2B	109.9	H8A—C8—H8C	109.5
H2A—C2—H2B	108.3	H8B—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1i	0.82	1.68	2.482 (12)	167

Table 1

Selected bond lengths (Å)

I1—Cu1	2.928 (2)
Cu1—O1	2.030 (9)
Cu1—N2	2.058 (11)
Cu1—N1	2.059 (10)
Cu1—O2	2.010 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1i	0.82	1.68	2.482 (12)	167

Symmetry code: (i) .