(4,4'-Dimethyl-2,2'-bipyridine-κ(2) N,N')(dimethyl-formamide-κO)diiodido-cadmium.

In the title compound, [CdI2(C12H12N2)(C3H7NO)], the Cd(II) cation is five-coordinated in a distorted trigonal-bipyramidal configuration by two N atoms from a 4,4'-dimethyl-2,2'-bipyridine ligand, one O atom from a dimethyl-formamide ligand and two I(-) anions. π-π stacking between pyridine rings of adjacent mol-ecules [centroid-centroid distance = 3.666 (3) and 3.709 (4) Å] stabilizes the three-dimensional structure.

Related literature

For related structures, see: Ahmadi et al. (2008 ▶); Alizadeh et al. (2010 ▶); Amani et al. (2009 ▶); Bellusci et al. (2008 ▶); Hojjat Kashani et al. (2008 ▶); Kalateh et al. (2008 ▶, 2010 ▶); Shirvan & Haydari Dezfuli (2012 ▶); Sofetis et al. (2006 ▶); Willett et al. (2001 ▶); Yousefi et al. (2008 ▶).

Experimental

Crystal data

[CdI2(C12n class="Species">H12N2)(C3H7NO)]

M = 623.54

Monoclinic,

a = 8.6103 (6) Å

b = 15.1325 (8) Å

c = 15.4263 (10) Å

β = 98.347 (5)°

V = 1988.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 4.21 mm−1

T = 298 K

0.45 × 0.40 × 0.35 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.188, T max = 0.223

12059 measured reflections

3907 independent reflections

2859 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.084

S = 0.98

3907 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −1.08 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046648/xu5650sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046648/xu5650Isup2.hkl

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

[CdI2(C12H12N2)(C3H7NO)]	F(000) = 1168
Mr = 623.54	Dx = 2.083 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12059 reflections
a = 8.6103 (6) Å	θ = 2.4–26.0°
b = 15.1325 (8) Å	µ = 4.21 mm−1
c = 15.4263 (10) Å	T = 298 K
β = 98.347 (5)°	Prism, colorless
V = 1988.7 (2) Å3	0.45 × 0.40 × 0.35 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3907 independent reflections
Radiation source: fine-focus sealed tube	2859 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→9
Tmin = 0.188, Tmax = 0.223	k = −18→17
12059 measured reflections	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0426P)2] where P = (Fo2 + 2Fc2)/3
3907 reflections	(Δ/σ)max = 0.007
199 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −1.08 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
C1	0.8789 (8)	−0.0736 (4)	0.0980 (3)	0.0488 (15)
H1	0.9275	−0.0965	0.1510	0.059*
C2	0.9026 (7)	−0.1170 (4)	0.0221 (4)	0.0477 (15)
H2	0.9664	−0.1668	0.0242	0.057*
C3	0.8286 (7)	−0.0843 (4)	−0.0571 (3)	0.0444 (14)
C4	0.8494 (9)	−0.1285 (5)	−0.1415 (4)	0.0619 (19)
H4A	0.8981	−0.0881	−0.1774	0.074*
H4B	0.7488	−0.1460	−0.1719	0.074*
H4C	0.9147	−0.1797	−0.1295	0.074*
C5	0.7387 (7)	−0.0090 (4)	−0.0555 (3)	0.0404 (14)
H5	0.6901	0.0149	−0.1080	0.049*
C6	0.7189 (7)	0.0318 (4)	0.0225 (3)	0.0353 (12)
C7	0.6243 (6)	0.1118 (4)	0.0260 (3)	0.0346 (12)
C8	0.5479 (7)	0.1536 (4)	−0.0481 (3)	0.0412 (14)
H8	0.5560	0.1305	−0.1031	0.049*
C9	0.4610 (8)	0.2282 (4)	−0.0416 (4)	0.0500 (16)
C10	0.3786 (10)	0.2740 (5)	−0.1238 (4)	0.070 (2)
H10A	0.3051	0.2340	−0.1559	0.083*
H10B	0.4550	0.2917	−0.1600	0.083*
H10C	0.3238	0.3252	−0.1074	0.083*
C11	0.4523 (8)	0.2614 (5)	0.0406 (4)	0.0552 (17)
H11	0.3936	0.3118	0.0477	0.066*
C12	0.5324 (8)	0.2183 (5)	0.1124 (4)	0.0546 (17)
H12	0.5279	0.2417	0.1677	0.066*
C13	1.0539 (9)	−0.0020 (5)	0.3557 (4)	0.0620 (19)
H13	1.0829	0.0570	0.3635	0.074*
C14	1.0840 (14)	−0.1519 (7)	0.4055 (6)	0.116 (4)
H14A	1.1070	−0.1741	0.3504	0.140*
H14B	0.9743	−0.1597	0.4087	0.140*
H14C	1.1450	−0.1836	0.4525	0.140*
C15	1.2436 (9)	−0.0323 (6)	0.4837 (4)	0.077 (3)
H15A	1.2016	0.0111	0.5193	0.092*
H15B	1.3308	−0.0074	0.4597	0.092*
H15C	1.2782	−0.0828	0.5188	0.092*
N1	0.7921 (6)	−0.0018 (3)	0.1005 (3)	0.0413 (12)
N2	0.6153 (6)	0.1455 (3)	0.1065 (3)	0.0408 (12)
N3	1.1228 (6)	−0.0590 (4)	0.4127 (3)	0.0526 (14)
O1	0.9541 (6)	−0.0201 (4)	0.2930 (3)	0.0708 (15)
Cd1	0.74180 (5)	0.06619 (3)	0.22889 (2)	0.04265 (13)
I1	0.51473 (6)	−0.03208 (3)	0.29304 (2)	0.05923 (15)
I2	0.84760 (6)	0.21673 (3)	0.32035 (3)	0.06213 (16)

	U11	U22	U33	U12	U13	U23
C1	0.066 (4)	0.042 (4)	0.035 (3)	0.010 (3)	−0.003 (3)	0.003 (2)
C2	0.051 (4)	0.045 (4)	0.047 (3)	0.010 (3)	0.006 (3)	−0.002 (3)
C3	0.046 (3)	0.047 (4)	0.041 (3)	−0.004 (3)	0.008 (2)	−0.006 (2)
C4	0.082 (5)	0.059 (5)	0.047 (3)	0.011 (4)	0.016 (3)	−0.012 (3)
C5	0.049 (4)	0.046 (4)	0.025 (2)	0.001 (3)	0.004 (2)	0.001 (2)
C6	0.038 (3)	0.039 (3)	0.028 (2)	−0.006 (3)	0.001 (2)	−0.001 (2)
C7	0.040 (3)	0.034 (3)	0.029 (2)	−0.002 (3)	0.001 (2)	0.001 (2)
C8	0.052 (4)	0.043 (4)	0.026 (2)	0.004 (3)	0.000 (2)	0.002 (2)
C9	0.062 (4)	0.047 (4)	0.038 (3)	0.002 (3)	−0.003 (3)	0.007 (2)
C10	0.090 (6)	0.066 (5)	0.050 (3)	0.028 (4)	0.000 (3)	0.015 (3)
C11	0.063 (4)	0.044 (4)	0.057 (4)	0.015 (3)	0.000 (3)	−0.001 (3)
C12	0.069 (5)	0.052 (4)	0.043 (3)	0.008 (4)	0.007 (3)	−0.009 (3)
C13	0.063 (5)	0.062 (5)	0.057 (4)	−0.001 (4)	−0.004 (3)	0.011 (3)
C14	0.162 (11)	0.083 (7)	0.085 (6)	−0.012 (7)	−0.044 (7)	0.003 (5)
C15	0.067 (5)	0.115 (7)	0.042 (3)	−0.008 (5)	−0.012 (3)	0.009 (4)
N1	0.048 (3)	0.044 (3)	0.029 (2)	0.001 (2)	−0.0041 (19)	0.0007 (19)
N2	0.047 (3)	0.044 (3)	0.031 (2)	0.000 (2)	0.0004 (19)	−0.0054 (19)
N3	0.058 (3)	0.067 (4)	0.029 (2)	0.004 (3)	−0.003 (2)	0.000 (2)
O1	0.077 (4)	0.077 (4)	0.048 (2)	0.011 (3)	−0.025 (2)	−0.007 (2)
Cd1	0.0527 (3)	0.0474 (3)	0.02556 (18)	−0.0051 (2)	−0.00212 (15)	−0.00121 (16)
I1	0.0755 (3)	0.0669 (3)	0.03425 (19)	−0.0214 (2)	0.00443 (18)	0.00662 (17)
I2	0.0806 (3)	0.0571 (3)	0.0446 (2)	−0.0157 (2)	−0.0047 (2)	−0.01291 (18)

C1—N1	1.322 (8)	C10—H10C	0.9600
C1—C2	1.383 (8)	C11—C12	1.380 (8)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.385 (8)	C12—N2	1.323 (8)
C2—H2	0.9300	C12—H12	0.9300
C3—C5	1.379 (9)	C13—O1	1.229 (8)
C3—C4	1.498 (8)	C13—N3	1.310 (8)
C4—H4A	0.9600	C13—H13	0.9300
C4—H4B	0.9600	C14—N3	1.445 (11)
C4—H4C	0.9600	C14—H14A	0.9600
C5—C6	1.384 (7)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—N1	1.373 (6)	C15—N3	1.454 (8)
C6—C7	1.464 (8)	C15—H15A	0.9600
C7—N2	1.355 (6)	C15—H15B	0.9600
C7—C8	1.386 (7)	C15—H15C	0.9600
C8—C9	1.367 (9)	Cd1—N1	2.327 (4)
C8—H8	0.9300	Cd1—N2	2.365 (4)
C9—C11	1.377 (9)	Cd1—O1	2.345 (5)
C9—C10	1.527 (8)	Cd1—I1	2.7523 (7)
C10—H10A	0.9600	Cd1—I2	2.7635 (6)
C10—H10B	0.9600
N1—C1—C2	124.6 (5)	N2—C12—C11	123.4 (5)
N1—C1—H1	117.7	N2—C12—H12	118.3
C2—C1—H1	117.7	C11—C12—H12	118.3
C1—C2—C3	118.1 (6)	O1—C13—N3	125.3 (7)
C1—C2—H2	120.9	O1—C13—H13	117.3
C3—C2—H2	120.9	N3—C13—H13	117.3
C5—C3—C2	117.8 (5)	N3—C14—H14A	109.5
C5—C3—C4	121.6 (5)	N3—C14—H14B	109.5
C2—C3—C4	120.6 (6)	H14A—C14—H14B	109.5
C3—C4—H4A	109.5	N3—C14—H14C	109.5
C3—C4—H4B	109.5	H14A—C14—H14C	109.5
H4A—C4—H4B	109.5	H14B—C14—H14C	109.5
C3—C4—H4C	109.5	N3—C15—H15A	109.5
H4A—C4—H4C	109.5	N3—C15—H15B	109.5
H4B—C4—H4C	109.5	H15A—C15—H15B	109.5
C3—C5—C6	121.7 (5)	N3—C15—H15C	109.5
C3—C5—H5	119.2	H15A—C15—H15C	109.5
C6—C5—H5	119.2	H15B—C15—H15C	109.5
N1—C6—C5	119.9 (5)	C1—N1—C6	117.9 (5)
N1—C6—C7	117.4 (4)	C1—N1—Cd1	124.4 (3)
C5—C6—C7	122.7 (5)	C6—N1—Cd1	117.6 (4)
N2—C7—C8	120.0 (5)	C12—N2—C7	118.7 (5)
N2—C7—C6	116.8 (4)	C12—N2—Cd1	123.9 (4)
C8—C7—C6	123.1 (5)	C7—N2—Cd1	117.4 (4)
C9—C8—C7	121.1 (5)	C13—N3—C14	120.8 (6)
C9—C8—H8	119.5	C13—N3—C15	121.7 (7)
C7—C8—H8	119.5	C14—N3—C15	117.4 (6)
C8—C9—C11	118.2 (5)	C13—O1—Cd1	128.4 (5)
C8—C9—C10	120.5 (5)	N1—Cd1—O1	83.23 (16)
C11—C9—C10	121.3 (6)	N1—Cd1—N2	70.51 (16)
C9—C10—H10A	109.5	O1—Cd1—N2	149.27 (18)
C9—C10—H10B	109.5	N1—Cd1—I1	107.25 (13)
H10A—C10—H10B	109.5	O1—Cd1—I1	95.65 (14)
C9—C10—H10C	109.5	N2—Cd1—I1	106.98 (12)
H10A—C10—H10C	109.5	N1—Cd1—I2	135.29 (13)
H10B—C10—H10C	109.5	O1—Cd1—I2	93.72 (12)
C9—C11—C12	118.7 (6)	N2—Cd1—I2	93.95 (12)
C9—C11—H11	120.7	I1—Cd1—I2	117.42 (2)
C12—C11—H11	120.7
N1—C1—C2—C3	−1.1 (11)	C6—C7—N2—C12	179.2 (6)
C1—C2—C3—C5	1.5 (9)	C8—C7—N2—Cd1	177.8 (4)
C1—C2—C3—C4	−179.9 (6)	C6—C7—N2—Cd1	−3.2 (6)
C2—C3—C5—C6	−1.6 (9)	O1—C13—N3—C14	−0.2 (13)
C4—C3—C5—C6	179.8 (6)	O1—C13—N3—C15	178.0 (7)
C3—C5—C6—N1	1.1 (9)	N3—C13—O1—Cd1	147.5 (6)
C3—C5—C6—C7	179.9 (6)	C1—N1—Cd1—O1	16.0 (5)
N1—C6—C7—N2	−0.8 (8)	C6—N1—Cd1—O1	−168.1 (4)
C5—C6—C7—N2	−179.6 (5)	C1—N1—Cd1—N2	179.8 (6)
N1—C6—C7—C8	178.2 (5)	C6—N1—Cd1—N2	−4.4 (4)
C5—C6—C7—C8	−0.6 (9)	C1—N1—Cd1—I1	−77.8 (5)
N2—C7—C8—C9	−0.9 (9)	C6—N1—Cd1—I1	98.0 (4)
C6—C7—C8—C9	−179.9 (6)	C1—N1—Cd1—I2	104.5 (5)
C7—C8—C9—C11	0.6 (10)	C6—N1—Cd1—I2	−79.7 (4)
C7—C8—C9—C10	179.5 (6)	C13—O1—Cd1—N1	146.2 (7)
C8—C9—C11—C12	0.5 (11)	C13—O1—Cd1—N2	115.2 (6)
C10—C9—C11—C12	−178.4 (7)	C13—O1—Cd1—I1	−107.0 (6)
C9—C11—C12—N2	−1.3 (11)	C13—O1—Cd1—I2	11.0 (6)
C2—C1—N1—C6	0.6 (10)	C12—N2—Cd1—N1	−178.6 (6)
C2—C1—N1—Cd1	176.4 (5)	C7—N2—Cd1—N1	4.0 (4)
C5—C6—N1—C1	−0.6 (8)	C12—N2—Cd1—O1	−145.7 (5)
C7—C6—N1—C1	−179.4 (6)	C7—N2—Cd1—O1	36.9 (6)
C5—C6—N1—Cd1	−176.7 (4)	C12—N2—Cd1—I1	78.7 (5)
C7—C6—N1—Cd1	4.5 (6)	C7—N2—Cd1—I1	−98.8 (4)
C11—C12—N2—C7	0.9 (10)	C12—N2—Cd1—I2	−41.6 (5)
C11—C12—N2—Cd1	−176.5 (5)	C7—N2—Cd1—I2	140.9 (4)
C8—C7—N2—C12	0.2 (9)

Table 1

Selected bond lengths (Å)

Cd1—N1	2.327 (4)
Cd1—N2	2.365 (4)
Cd1—O1	2.345 (5)
Cd1—I1	2.7523 (7)
Cd1—I2	2.7635 (6)