Dibromido(2,9-dimethyl-1,10-phenanthroline-κN,N')cadmium.

In the title complex, [CdBr(2)(C(14)H(12)N(2))], the Cd(II) ion is tetra-coordinated by two N atoms of the bidentate 2,9-dimethyl-1,10-phenanthroline ligand and two bromide ions in a substanti-ally distorted CdN(2)Br(2) tetra-hedral geometry. In the crystal, inversion dimers linked by pairs of weak C-H⋯Br bonds generate R(2) (2)(14) loops. Aromatic π-π stacking [shortest centroid-centroid separation = 3.633 (2) Å] inter-actions occur within, and also link, the dimers into chains propagating parallel to [100].

Related literature

For related structures, see: Preston & Kennard (1969 ▶); Lange et al. (2000 ▶); Alizadeh et al. (2009 ▶); Wang & Zhong (2009 ▶); Warad et al. (2011 ▶). For background to π–π stacking inter­actions, see: Janiak (2000 ▶).

Experimental

Crystal data

[CdBr2(C14H12N2)]

M = 480.48

Monoclinic,

a = 7.889 (4) Å

b = 10.519 (3) Å

c = 18.712 (2) Å

β = 97.69 (3)°

V = 1538.8 (9) Å3

Z = 4

Ag Kα radiation

λ = 0.56087 Å

μ = 3.53 mm−1

T = 293 K

0.30 × 0.25 × 0.17 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.469, T max = 0.534

9813 measured reflections

7516 independent reflections

2986 reflections with I > 2σ(I)

R int = 0.029

2 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.177

S = 0.98

7516 reflections

174 parameters

H-atom parameters constrained

Δρmax = 1.41 e Å−3

Δρmin = −0.93 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: SHELXS86 (Sheldrick, 2008 ▶); 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/S1600536811050069/hb6522sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050069/hb6522Isup2.hkl

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

[CdBr2(C14H12N2)]	F(000) = 912
Mr = 480.48	Dx = 2.074 Mg m−3
Monoclinic, P21/c	Ag Kα radiation, λ = 0.56087 Å
a = 7.889 (4) Å	Cell parameters from 25 reflections
b = 10.519 (3) Å	θ = 9–11°
c = 18.712 (2) Å	µ = 3.53 mm−1
β = 97.69 (3)°	T = 293 K
V = 1538.8 (9) Å3	Prism, colorless
Z = 4	0.30 × 0.25 × 0.17 mm

Enraf–Nonius CAD-4 diffractometer	2986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 28.0°, θmin = 2.1°
non–profiled ω scans	h = −13→13
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −2→17
Tmin = 0.469, Tmax = 0.534	l = −2→31
9813 measured reflections	2 standard reflections every 120 min
7516 independent reflections	intensity decay: 1%

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0769P)2] where P = (Fo2 + 2Fc2)/3
7516 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 1.41 e Å−3
0 restraints	Δρmin = −0.93 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	0.71490 (5)	0.28442 (4)	0.39225 (2)	0.05032 (14)
Br1	0.44548 (9)	0.32557 (8)	0.30765 (4)	0.0833 (2)
Br2	0.93295 (10)	0.45768 (6)	0.39288 (4)	0.0766 (2)
N1	0.6886 (5)	0.1781 (4)	0.4972 (2)	0.0422 (8)
N2	0.8075 (5)	0.0829 (4)	0.3769 (2)	0.0409 (8)
C1	0.6270 (6)	0.2257 (5)	0.5546 (3)	0.0501 (11)
C2	0.6113 (7)	0.1479 (6)	0.6149 (3)	0.0561 (13)
H2	0.5692	0.1819	0.6549	0.067*
C3	0.6578 (7)	0.0234 (6)	0.6146 (3)	0.0553 (14)
H3	0.6462	−0.0278	0.6541	0.066*
C4	0.7229 (6)	−0.0278 (5)	0.5551 (3)	0.0462 (11)
C5	0.7760 (6)	−0.1572 (5)	0.5505 (3)	0.0562 (13)
H5	0.7680	−0.2113	0.5892	0.067*
C6	0.8373 (7)	−0.2031 (5)	0.4918 (3)	0.0530 (12)
H6	0.8724	−0.2875	0.4910	0.064*
C7	0.8489 (6)	−0.1248 (4)	0.4314 (3)	0.0412 (10)
C8	0.9065 (6)	−0.1674 (5)	0.3680 (3)	0.0511 (12)
H8	0.9394	−0.2518	0.3644	0.061*
C9	0.9152 (7)	−0.0873 (5)	0.3119 (3)	0.0535 (12)
H9	0.9543	−0.1166	0.2702	0.064*
C10	0.8653 (7)	0.0387 (5)	0.3170 (3)	0.0518 (12)
C11	0.7981 (5)	0.0045 (4)	0.4331 (2)	0.0375 (9)
C12	0.7359 (5)	0.0532 (4)	0.4963 (2)	0.0389 (10)
C13	0.5798 (8)	0.3629 (6)	0.5518 (3)	0.0663 (16)
H13A	0.6777	0.4129	0.5704	0.100*
H13B	0.4894	0.3773	0.5805	0.100*
H13C	0.5421	0.3870	0.5028	0.100*
C14	0.8682 (10)	0.1297 (6)	0.2557 (3)	0.079 (2)
H14A	0.7966	0.2013	0.2624	0.119*
H14B	0.8266	0.0879	0.2112	0.119*
H14C	0.9833	0.1582	0.2543	0.119*

	U11	U22	U33	U12	U13	U23
Cd1	0.0656 (3)	0.03953 (19)	0.0473 (2)	0.00785 (18)	0.01316 (17)	0.00728 (16)
Br1	0.0686 (4)	0.1170 (6)	0.0645 (4)	0.0160 (4)	0.0094 (3)	0.0320 (4)
Br2	0.1037 (5)	0.0481 (3)	0.0791 (4)	−0.0126 (3)	0.0164 (4)	0.0111 (3)
N1	0.047 (2)	0.042 (2)	0.0384 (19)	−0.0033 (17)	0.0057 (16)	0.0018 (16)
N2	0.045 (2)	0.0379 (19)	0.0400 (19)	0.0016 (16)	0.0067 (17)	0.0003 (16)
C1	0.041 (2)	0.058 (3)	0.052 (3)	−0.002 (2)	0.009 (2)	−0.005 (3)
C2	0.050 (3)	0.076 (4)	0.044 (3)	−0.004 (3)	0.013 (2)	−0.006 (3)
C3	0.049 (3)	0.076 (4)	0.042 (3)	−0.010 (3)	0.009 (2)	0.012 (3)
C4	0.039 (2)	0.056 (3)	0.043 (2)	−0.005 (2)	0.006 (2)	0.011 (2)
C5	0.054 (3)	0.052 (3)	0.061 (3)	−0.003 (3)	0.004 (3)	0.021 (3)
C6	0.054 (3)	0.039 (2)	0.066 (3)	0.000 (2)	0.005 (3)	0.013 (2)
C7	0.036 (2)	0.037 (2)	0.050 (3)	−0.0016 (18)	0.003 (2)	0.006 (2)
C8	0.051 (3)	0.038 (2)	0.064 (3)	0.007 (2)	0.007 (2)	−0.009 (2)
C9	0.062 (3)	0.047 (3)	0.053 (3)	0.003 (2)	0.011 (2)	−0.008 (2)
C10	0.063 (3)	0.051 (3)	0.042 (2)	0.000 (2)	0.010 (2)	−0.006 (2)
C11	0.033 (2)	0.038 (2)	0.040 (2)	−0.0021 (17)	−0.0001 (18)	−0.0001 (18)
C12	0.034 (2)	0.039 (2)	0.042 (2)	−0.0026 (18)	−0.0004 (18)	0.0068 (19)
C13	0.082 (4)	0.057 (3)	0.065 (4)	0.008 (3)	0.026 (3)	−0.010 (3)
C14	0.129 (6)	0.060 (4)	0.057 (3)	0.013 (4)	0.041 (4)	0.006 (3)

Cd1—N2	2.273 (4)	C5—H5	0.9300
Cd1—N1	2.294 (4)	C6—C7	1.412 (7)
Cd1—Br2	2.5050 (10)	C6—H6	0.9300
Cd1—Br1	2.5120 (13)	C7—C8	1.399 (7)
N1—C1	1.334 (6)	C7—C11	1.419 (6)
N1—C12	1.367 (6)	C8—C9	1.355 (8)
N2—C11	1.347 (6)	C8—H8	0.9300
N2—C10	1.348 (6)	C9—C10	1.389 (7)
C1—C2	1.412 (8)	C9—H9	0.9300
C1—C13	1.489 (8)	C10—C14	1.496 (8)
C2—C3	1.360 (8)	C11—C12	1.433 (6)
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.395 (7)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C12	1.405 (6)	C14—H14A	0.9600
C4—C5	1.430 (8)	C14—H14B	0.9600
C5—C6	1.347 (8)	C14—H14C	0.9600
N2—Cd1—N1	73.81 (14)	C8—C7—C6	123.7 (4)
N2—Cd1—Br2	116.56 (10)	C8—C7—C11	116.8 (4)
N1—Cd1—Br2	119.43 (10)	C6—C7—C11	119.5 (5)
N2—Cd1—Br1	109.88 (10)	C9—C8—C7	120.9 (5)
N1—Cd1—Br1	117.25 (10)	C9—C8—H8	119.6
Br2—Cd1—Br1	113.59 (4)	C7—C8—H8	119.6
C1—N1—C12	120.1 (4)	C8—C9—C10	119.7 (5)
C1—N1—Cd1	126.2 (3)	C8—C9—H9	120.1
C12—N1—Cd1	113.6 (3)	C10—C9—H9	120.1
C11—N2—C10	119.9 (4)	N2—C10—C9	121.1 (5)
C11—N2—Cd1	114.8 (3)	N2—C10—C14	117.3 (5)
C10—N2—Cd1	125.2 (3)	C9—C10—C14	121.6 (5)
N1—C1—C2	120.4 (5)	N2—C11—C7	121.6 (4)
N1—C1—C13	116.8 (5)	N2—C11—C12	119.1 (4)
C2—C1—C13	122.8 (5)	C7—C11—C12	119.4 (4)
C3—C2—C1	120.1 (5)	N1—C12—C4	121.5 (4)
C3—C2—H2	119.9	N1—C12—C11	118.6 (4)
C1—C2—H2	119.9	C4—C12—C11	119.8 (4)
C2—C3—C4	120.2 (5)	C1—C13—H13A	109.5
C2—C3—H3	119.9	C1—C13—H13B	109.5
C4—C3—H3	119.9	H13A—C13—H13B	109.5
C3—C4—C12	117.7 (5)	C1—C13—H13C	109.5
C3—C4—C5	123.9 (5)	H13A—C13—H13C	109.5
C12—C4—C5	118.5 (5)	H13B—C13—H13C	109.5
C6—C5—C4	122.0 (5)	C10—C14—H14A	109.5
C6—C5—H5	119.0	C10—C14—H14B	109.5
C4—C5—H5	119.0	H14A—C14—H14B	109.5
C5—C6—C7	120.8 (5)	C10—C14—H14C	109.5
C5—C6—H6	119.6	H14A—C14—H14C	109.5
C7—C6—H6	119.6	H14B—C14—H14C	109.5
N2—Cd1—N1—C1	−178.5 (4)	C7—C8—C9—C10	−0.4 (8)
Br2—Cd1—N1—C1	69.7 (4)	C11—N2—C10—C9	0.3 (8)
Br1—Cd1—N1—C1	−74.1 (4)	Cd1—N2—C10—C9	−178.3 (4)
N2—Cd1—N1—C12	−1.4 (3)	C11—N2—C10—C14	178.4 (5)
Br2—Cd1—N1—C12	−113.2 (3)	Cd1—N2—C10—C14	−0.2 (7)
Br1—Cd1—N1—C12	103.0 (3)	C8—C9—C10—N2	−0.3 (8)
N1—Cd1—N2—C11	1.3 (3)	C8—C9—C10—C14	−178.4 (6)
Br2—Cd1—N2—C11	116.6 (3)	C10—N2—C11—C7	0.4 (7)
Br1—Cd1—N2—C11	−112.4 (3)	Cd1—N2—C11—C7	179.1 (3)
N1—Cd1—N2—C10	180.0 (4)	C10—N2—C11—C12	−179.9 (4)
Br2—Cd1—N2—C10	−64.7 (4)	Cd1—N2—C11—C12	−1.1 (5)
Br1—Cd1—N2—C10	66.3 (4)	C8—C7—C11—N2	−1.0 (6)
C12—N1—C1—C2	0.5 (7)	C6—C7—C11—N2	179.8 (4)
Cd1—N1—C1—C2	177.4 (4)	C8—C7—C11—C12	179.2 (4)
C12—N1—C1—C13	179.4 (5)	C6—C7—C11—C12	0.0 (6)
Cd1—N1—C1—C13	−3.6 (6)	C1—N1—C12—C4	−0.6 (7)
N1—C1—C2—C3	−0.5 (8)	Cd1—N1—C12—C4	−177.8 (3)
C13—C1—C2—C3	−179.5 (5)	C1—N1—C12—C11	178.7 (4)
C1—C2—C3—C4	0.7 (8)	Cd1—N1—C12—C11	1.4 (5)
C2—C3—C4—C12	−0.8 (7)	C3—C4—C12—N1	0.7 (7)
C2—C3—C4—C5	179.5 (5)	C5—C4—C12—N1	−179.5 (4)
C3—C4—C5—C6	179.6 (5)	C3—C4—C12—C11	−178.5 (4)
C12—C4—C5—C6	−0.1 (8)	C5—C4—C12—C11	1.2 (7)
C4—C5—C6—C7	−1.1 (8)	N2—C11—C12—N1	−0.2 (6)
C5—C6—C7—C8	−178.1 (5)	C7—C11—C12—N1	179.6 (4)
C5—C6—C7—C11	1.1 (7)	N2—C11—C12—C4	179.0 (4)
C6—C7—C8—C9	−179.8 (5)	C7—C11—C12—C4	−1.2 (6)
C11—C7—C8—C9	1.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Br1i	0.93	2.98	3.805 (5)	149

Cd1—N2	2.273 (4)
Cd1—N1	2.294 (4)
Cd1—Br2	2.5050 (10)
Cd1—Br1	2.5120 (13)

N2—Cd1—N1

73.81 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Br1i	0.93	2.98	3.805 (5)	149

Symmetry code: (i) .