Dichlorido(2,9-dimethyl-1,10-phenanthroline-κN,N')copper(II).

In the title compound, [CuCl(2)(C(14)H(12)N(2))], the complex molecule has m symmetry, with the mirror plane oriented parallel to the planar molecule and the ligated Cu(II) atom. The metal centre has a distorted tetra-hedral coordination formed by two N atoms from one 2,9-dimethyl-1,10-phenanthroline ligand and two Cl atoms. There is inter-molecular π-π stacking between adjacent 2,9-dimethyl-1,10-phenanthroline ligands, with a centroid-centroid distance of 3.733 (2)Å.

Related literature

For backgroud to π-π stacking in metal complexes of n class="Chemical">phenanthroline and its derivatives, benzimidazole and quinoline, see: Wall et al. (1999 ▶); Wu et al. (2003 ▶); Pan & Xu (2004 ▶); Li et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[CuCl2(n class="CellLine">C14H12N2)]

M = 342.70

Orthorhombic,

a = 11.239 (2) Å

b = 7.4651 (18) Å

c = 17.663 (5) Å

V = 1481.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.82 mm−1

T = 273 K

0.30 × 0.28 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.611, T max = 0.701

10738 measured reflections

1951 independent reflections

1601 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.083

S = 1.00

1951 reflections

114 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (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.

Crystal structure: contains datablocks global. DOI: 10.1107/S1600536809034187/at2860sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034187/at2860Isup2.hkl

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

[CuCl2(C14H12N2)]	F(000) = 692
Mr = 342.70	Dx = 1.536 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 5426 reflections
a = 11.239 (2) Å	θ = 2.3–28.0°
b = 7.4651 (18) Å	µ = 1.82 mm−1
c = 17.663 (5) Å	T = 273 K
V = 1481.9 (6) Å3	Plane, blue
Z = 4	0.30 × 0.28 × 0.21 mm

Bruker APEXII area-detector diffractometer	1951 independent reflections
Radiation source: fine-focus sealed tube	1601 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→14
Tmin = 0.611, Tmax = 0.701	k = −9→9
10738 measured reflections	l = −23→23

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.1694P] where P = (Fo2 + 2Fc2)/3
1951 reflections	(Δ/σ)max = 0.001
114 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.29 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	Occ. (<1)
Cu1	0.76127 (2)	0.7500	0.610028 (14)	0.04178 (12)
N1	0.79467 (16)	0.7500	0.49476 (10)	0.0418 (4)
N2	0.58758 (17)	0.7500	0.57229 (11)	0.0445 (4)
C1	1.0098 (2)	0.7500	0.50503 (18)	0.0684 (8)
H1A	1.0316	0.8711	0.5170	0.103*	0.50
H1B	1.0728	0.6946	0.4767	0.103*	0.50
H1C	0.9967	0.6843	0.5510	0.103*	0.50
C13	0.6920 (2)	0.7500	0.45450 (12)	0.0406 (5)
C11	0.4872 (3)	0.7500	0.61234 (14)	0.0558 (6)
C2	0.8982 (2)	0.7500	0.45874 (15)	0.0517 (6)
C12	0.58155 (19)	0.7500	0.49535 (12)	0.0403 (5)
C14	0.4987 (3)	0.7500	0.69623 (17)	0.0803 (10)
H14A	0.5697	0.8130	0.7105	0.120*	0.50
H14B	0.5030	0.6288	0.7142	0.120*	0.50
H14C	0.4307	0.8082	0.7182	0.120*	0.50
C10	0.3763 (2)	0.7500	0.5751 (2)	0.0711 (8)
H10	0.3067	0.7500	0.6035	0.085*
C8	0.4741 (2)	0.7500	0.45551 (15)	0.0500 (6)
C7	0.4757 (3)	0.7500	0.37518 (16)	0.0624 (7)
H7	0.4041	0.7500	0.3487	0.075*
C5	0.6901 (2)	0.7500	0.37527 (13)	0.0502 (6)
C6	0.5787 (3)	0.7500	0.33689 (15)	0.0610 (7)
H6	0.5774	0.7500	0.2842	0.073*
C9	0.3695 (2)	0.7500	0.49900 (19)	0.0664 (8)
H9	0.2957	0.7500	0.4753	0.080*
C3	0.9025 (3)	0.7500	0.37937 (16)	0.0676 (8)
H3	0.9756	0.7500	0.3547	0.081*
C4	0.8005 (3)	0.7500	0.33845 (16)	0.0687 (8)
H4	0.8038	0.7500	0.2858	0.082*
Cl1	0.81305 (5)	1.00503 (6)	0.66249 (3)	0.06566 (17)

	U11	U22	U33	U12	U13	U23
Cu1	0.04754 (18)	0.0423 (2)	0.03548 (17)	0.000	−0.00528 (11)	0.000
N1	0.0374 (9)	0.0471 (11)	0.0408 (10)	0.000	0.0006 (8)	0.000
N2	0.0450 (10)	0.0441 (11)	0.0446 (10)	0.000	0.0081 (8)	0.000
C1	0.0403 (13)	0.082 (2)	0.083 (2)	0.000	−0.0043 (13)	0.000
C13	0.0403 (11)	0.0429 (13)	0.0387 (10)	0.000	0.0002 (9)	0.000
C11	0.0560 (14)	0.0532 (16)	0.0581 (15)	0.000	0.0192 (12)	0.000
C2	0.0404 (11)	0.0570 (16)	0.0576 (14)	0.000	0.0053 (10)	0.000
C12	0.0393 (11)	0.0395 (12)	0.0421 (11)	0.000	0.0014 (9)	0.000
C14	0.094 (2)	0.090 (2)	0.0565 (16)	0.000	0.0325 (17)	0.000
C10	0.0436 (14)	0.078 (2)	0.092 (2)	0.000	0.0226 (15)	0.000
C8	0.0412 (12)	0.0492 (14)	0.0596 (14)	0.000	−0.0044 (10)	0.000
C7	0.0556 (15)	0.0730 (19)	0.0586 (15)	0.000	−0.0195 (12)	0.000
C5	0.0559 (14)	0.0558 (16)	0.0388 (11)	0.000	0.0009 (10)	0.000
C6	0.0660 (17)	0.0736 (19)	0.0434 (13)	0.000	−0.0118 (12)	0.000
C9	0.0372 (12)	0.078 (2)	0.084 (2)	0.000	0.0030 (12)	0.000
C3	0.0508 (15)	0.096 (2)	0.0560 (16)	0.000	0.0176 (12)	0.000
C4	0.0656 (17)	0.095 (3)	0.0449 (14)	0.000	0.0135 (13)	0.000
Cl1	0.0766 (3)	0.0502 (3)	0.0702 (3)	−0.0019 (2)	−0.0167 (3)	−0.0113 (2)

Cu1—Cl1	2.1958 (6)	C12—C8	1.398 (3)
Cu1—Cl1i	2.1958 (6)	C14—H14A	0.9600
Cu1—N1	2.070 (2)	C14—H14B	0.9600
Cu1—N2	2.063 (2)	C14—H14C	0.9600
N1—C2	1.326 (3)	C10—C9	1.346 (5)
N1—C13	1.355 (3)	C10—H10	0.9300
N2—C11	1.331 (3)	C8—C9	1.404 (4)
N2—C12	1.361 (3)	C8—C7	1.419 (4)
C1—C2	1.498 (4)	C7—C6	1.341 (4)
C1—H1A	0.9600	C7—H7	0.9300
C1—H1B	0.9600	C5—C4	1.401 (4)
C1—H1C	0.9600	C5—C6	1.423 (4)
C13—C5	1.400 (3)	C6—H6	0.9300
C13—C12	1.436 (3)	C9—H9	0.9300
C11—C10	1.409 (4)	C3—C4	1.355 (4)
C11—C14	1.487 (4)	C3—H3	0.9300
C2—C3	1.403 (3)	C4—H4	0.9300
Cl1—Cu1—Cl1i	120.23 (3)	C11—C14—H14A	109.5
N1—Cu1—Cl1	111.53 (3)	C11—C14—H14B	109.5
N1—Cu1—Cl1i	111.53 (3)	H14A—C14—H14B	109.5
N2—Cu1—N1	81.60 (7)	C11—C14—H14C	109.5
N2—Cu1—Cl1	112.78 (2)	H14A—C14—H14C	109.5
N2—Cu1—Cl1i	112.78 (2)	H14B—C14—H14C	109.5
C2—N1—C13	119.7 (2)	C9—C10—C11	121.1 (3)
C2—N1—Cu1	129.12 (17)	C9—C10—H10	119.4
C13—N1—Cu1	111.21 (15)	C11—C10—H10	119.4
C11—N2—C12	119.2 (2)	C12—C8—C9	116.6 (2)
C11—N2—Cu1	129.05 (18)	C12—C8—C7	119.5 (2)
C12—N2—Cu1	111.71 (14)	C9—C8—C7	123.9 (2)
C2—C1—H1A	109.5	C6—C7—C8	121.0 (2)
C2—C1—H1B	109.5	C6—C7—H7	119.5
H1A—C1—H1B	109.5	C8—C7—H7	119.5
C2—C1—H1C	109.5	C13—C5—C4	116.7 (2)
H1A—C1—H1C	109.5	C13—C5—C6	119.4 (2)
H1B—C1—H1C	109.5	C4—C5—C6	123.9 (2)
N1—C13—C5	122.6 (2)	C7—C6—C5	121.3 (2)
N1—C13—C12	118.2 (2)	C7—C6—H6	119.4
C5—C13—C12	119.2 (2)	C5—C6—H6	119.4
N2—C11—C10	120.1 (2)	C10—C9—C8	119.9 (3)
N2—C11—C14	117.1 (3)	C10—C9—H9	120.0
C10—C11—C14	122.8 (3)	C8—C9—H9	120.0
N1—C2—C3	120.6 (2)	C4—C3—C2	120.3 (2)
N1—C2—C1	118.2 (2)	C4—C3—H3	119.9
C3—C2—C1	121.1 (2)	C2—C3—H3	119.9
N2—C12—C8	123.1 (2)	C3—C4—C5	120.1 (3)
N2—C12—C13	117.30 (19)	C3—C4—H4	119.9
C8—C12—C13	119.6 (2)	C5—C4—H4	119.9