(2,9-Dimethyl-1,10-phenanthroline-κN,N')diiodidocadmium.

In the title compound, [CdI(2)(C(14)H(12)N(2))], the mol-ecule sits on a crystallographic twofold axis. The coordination sphere of the Cd(II) atom is built of two symmetry-equivalent N atoms of one 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand and two symmetry-equivalent I atoms, thus forming a distorted tetra-hedral geometry. Inversion-related mol-ecules inter-act along the c-axis direction by π-π stacking inter-actions between the phenanthroline ring systems, with centroid-centroid distances of 3.707 (9) and 3.597 (10) Å.

Related literature

For coordination chemistry of phenanthroline derivatives and their applications, see: Miller et al. (1999 ▶); Bodoki et al. (2009 ▶); Kane-Maguire & Wheeler (2001 ▶); Shahabadi et al. (2009 ▶). For related structures involving 2,9-dimethyl-1,10-phenanthroline, see: Alizadeh et al. (2009 ▶); Preston & Kennard (1969 ▶); Wang & Zhong (2009 ▶). For background information on π–π stacking inter­actions, see: Janiak (2000 ▶).

Experimental

Crystal data

[CdI2(C14H12N2)]

M = 574.46

Monoclinic,

a = 15.690 (3) Å

b = 11.580 (2) Å

c = 9.836 (5) Å

β = 114.65 (4)°

V = 1624.3 (9) Å3

Z = 4

Ag Kα radiation

λ = 0.56087 Å

μ = 2.72 mm−1

T = 293 K

0.35 × 0.23 × 0.19 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.563, T max = 0.605

6126 measured reflections

3986 independent reflections

2306 reflections with I > 2σ(I)

R int = 0.020

2 standard reflections every 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.127

S = 1.02

3986 reflections

88 parameters

H-atom parameters constrained

Δρmax = 1.65 e Å−3

Δρmin = −1.30 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811044667/pk2353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044667/pk2353Isup2.hkl

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

[CdI2(C14H12N2)]	F(000) = 1056
Mr = 574.46	Dx = 2.349 Mg m−3
Monoclinic, C2/c	Ag Kα radiation, λ = 0.56087 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 15.690 (3) Å	θ = 9–11°
b = 11.580 (2) Å	µ = 2.72 mm−1
c = 9.836 (5) Å	T = 293 K
β = 114.65 (4)°	Prism, colorless
V = 1624.3 (9) Å3	0.35 × 0.23 × 0.19 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2306 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 28.0°, θmin = 2.2°
non–profiled ω scans	h = −26→25
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −2→19
Tmin = 0.563, Tmax = 0.605	l = −3→16
6126 measured reflections	2 standard reflections every 120 min
3986 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.056P)2 + 2.6748P] where P = (Fo2 + 2Fc2)/3
3986 reflections	(Δ/σ)max = 0.001
88 parameters	Δρmax = 1.65 e Å−3
0 restraints	Δρmin = −1.30 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
Cd1	0.5000	0.30673 (3)	0.2500	0.04219 (11)
I1	0.63145 (2)	0.40526 (3)	0.49576 (4)	0.06297 (13)
N1	0.4331 (2)	0.1468 (3)	0.3059 (3)	0.0385 (6)
C1	0.3676 (3)	0.1493 (4)	0.3594 (4)	0.0456 (8)
C2	0.3328 (3)	0.0468 (5)	0.3921 (5)	0.0547 (10)
H2	0.2873	0.0495	0.4293	0.066*
C3	0.3655 (3)	−0.0567 (4)	0.3697 (5)	0.0546 (11)
H3	0.3436	−0.1246	0.3943	0.066*
C4	0.4325 (3)	−0.0616 (3)	0.3093 (4)	0.0470 (9)
C5	0.4652 (2)	0.0441 (3)	0.2803 (4)	0.0375 (7)
C6	0.4684 (4)	−0.1672 (4)	0.2796 (5)	0.0571 (11)
H6	0.4478	−0.2370	0.3017	0.069*
C7	0.3344 (3)	0.2640 (5)	0.3834 (6)	0.0615 (12)
H7A	0.3819	0.2997	0.4698	0.092*
H7B	0.2782	0.2548	0.3988	0.092*
H7C	0.3215	0.3116	0.2972	0.092*

	U11	U22	U33	U12	U13	U23
Cd1	0.0423 (2)	0.03666 (19)	0.0490 (2)	0.000	0.02046 (17)	0.000
I1	0.0659 (2)	0.0604 (2)	0.0597 (2)	−0.02133 (15)	0.02329 (16)	−0.01232 (14)
N1	0.0341 (13)	0.0426 (16)	0.0372 (15)	−0.0004 (11)	0.0133 (11)	0.0038 (12)
C1	0.0387 (16)	0.057 (2)	0.0416 (19)	−0.0006 (16)	0.0175 (15)	0.0072 (17)
C2	0.0426 (19)	0.073 (3)	0.045 (2)	−0.010 (2)	0.0150 (17)	0.011 (2)
C3	0.054 (2)	0.058 (2)	0.041 (2)	−0.0205 (19)	0.0087 (17)	0.0072 (18)
C4	0.053 (2)	0.0424 (19)	0.0335 (17)	−0.0112 (16)	0.0067 (16)	0.0012 (15)
C5	0.0385 (15)	0.0361 (16)	0.0292 (15)	−0.0038 (13)	0.0053 (12)	0.0004 (13)
C6	0.081 (3)	0.0360 (18)	0.044 (2)	−0.0105 (19)	0.016 (2)	0.0021 (16)
C7	0.059 (2)	0.070 (3)	0.068 (3)	0.015 (2)	0.039 (2)	0.009 (2)

Cd1—N1i	2.305 (3)	C3—C4	1.407 (7)
Cd1—N1	2.305 (3)	C3—H3	0.9300
Cd1—I1	2.6907 (14)	C4—C5	1.401 (5)
Cd1—I1i	2.6907 (14)	C4—C6	1.427 (6)
N1—C1	1.337 (5)	C5—C5i	1.447 (8)
N1—C5	1.355 (5)	C6—C6i	1.343 (11)
C1—C2	1.399 (6)	C6—H6	0.9300
C1—C7	1.481 (6)	C7—H7A	0.9600
C2—C3	1.357 (7)	C7—H7B	0.9600
C2—H2	0.9300	C7—H7C	0.9600
N1i—Cd1—N1	73.05 (16)	C4—C3—H3	119.9
N1i—Cd1—I1	107.48 (8)	C5—C4—C3	116.9 (4)
N1—Cd1—I1	112.40 (8)	C5—C4—C6	119.8 (4)
N1i—Cd1—I1i	112.40 (8)	C3—C4—C6	123.3 (4)
N1—Cd1—I1i	107.48 (8)	N1—C5—C4	122.2 (4)
I1—Cd1—I1i	129.82 (4)	N1—C5—C5i	118.6 (2)
C1—N1—C5	119.9 (3)	C4—C5—C5i	119.2 (2)
C1—N1—Cd1	125.3 (3)	C6i—C6—C4	121.0 (3)
C5—N1—Cd1	114.9 (2)	C6i—C6—H6	119.5
N1—C1—C2	120.6 (4)	C4—C6—H6	119.5
N1—C1—C7	117.5 (4)	C1—C7—H7A	109.5
C2—C1—C7	121.8 (4)	C1—C7—H7B	109.5
C3—C2—C1	120.1 (4)	H7A—C7—H7B	109.5
C3—C2—H2	119.9	C1—C7—H7C	109.5
C1—C2—H2	119.9	H7A—C7—H7C	109.5
C2—C3—C4	120.2 (4)	H7B—C7—H7C	109.5
C2—C3—H3	119.9
N1i—Cd1—N1—C1	−179.5 (4)	C2—C3—C4—C5	2.4 (6)
I1—Cd1—N1—C1	78.1 (3)	C2—C3—C4—C6	−178.6 (4)
I1i—Cd1—N1—C1	−70.8 (3)	C1—N1—C5—C4	−0.6 (5)
N1i—Cd1—N1—C5	0.37 (17)	Cd1—N1—C5—C4	179.5 (3)
I1—Cd1—N1—C5	−102.0 (2)	C1—N1—C5—C5i	178.9 (4)
I1i—Cd1—N1—C5	109.1 (2)	Cd1—N1—C5—C5i	−1.0 (5)
C5—N1—C1—C2	1.3 (6)	C3—C4—C5—N1	−1.2 (5)
Cd1—N1—C1—C2	−178.8 (3)	C6—C4—C5—N1	179.8 (4)
C5—N1—C1—C7	−179.3 (4)	C3—C4—C5—C5i	179.3 (4)
Cd1—N1—C1—C7	0.6 (5)	C6—C4—C5—C5i	0.3 (6)
N1—C1—C2—C3	0.0 (6)	C5—C4—C6—C6i	−1.8 (8)
C7—C1—C2—C3	−179.5 (5)	C3—C4—C6—C6i	179.3 (5)
C1—C2—C3—C4	−1.9 (6)