metal-organic compounds
(4,4′-Dimethyl-2,2′-bipyridine-κ2N,N′)(dimethylformamide-κO)diiodidocadmium
aDepartment of Chemistry, Omidieh Branch, Islamic Azad University, Omidieh, Iran, and bDepartment of Petroleum Engineering, Omidieh Branch, Islamic Azad University, Omidieh, Iran
*Correspondence e-mail: sadifchemist@hotmail.com
In the title compound, [CdI2(C12H12N2)(C3H7NO)], the CdII 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 dimethylformamide ligand and two I− anions. π–π stacking between pyridine rings of adjacent molecules [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
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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.
Supporting information
10.1107/S1600536812046648/xu5650sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812046648/xu5650Isup2.hkl
For the preparation of the title compound, a solution of 4,4'-dimethyl-2,2'-bipyridine (0.15 g, 0.80 mmol) in methanol (10 ml) was added to a solution of CdI2, (0.29 g, 0.80 mmol) in methanol (5 ml) at room temperature. The suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion to a colorless solution in dimethylformamide. Suitable crystals were isolated after one week (yield; 0.37 g, 74.2%).
H atoms were positioned geometrically with C—H = 0.93– 0.96 Å and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[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 |
[CdI2(C12H12N2)(C3H7NO)] | V = 1988.7 (2) Å3 |
Mr = 623.54 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.6103 (6) Å | µ = 4.21 mm−1 |
b = 15.1325 (8) Å | T = 298 K |
c = 15.4263 (10) Å | 0.45 × 0.40 × 0.35 mm |
β = 98.347 (5)° |
Bruker APEXII CCD area-detector diffractometer | 3907 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2859 reflections with I > 2σ(I) |
Tmin = 0.188, Tmax = 0.223 | Rint = 0.052 |
12059 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.85 e Å−3 |
3907 reflections | Δρmin = −1.08 e Å−3 |
199 parameters |
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) |
Experimental details
Crystal data | |
Chemical formula | [CdI2(C12H12N2)(C3H7NO)] |
Mr | 623.54 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 8.6103 (6), 15.1325 (8), 15.4263 (10) |
β (°) | 98.347 (5) |
V (Å3) | 1988.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.21 |
Crystal size (mm) | 0.45 × 0.40 × 0.35 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.188, 0.223 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12059, 3907, 2859 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.084, 0.98 |
No. of reflections | 3907 |
No. of parameters | 199 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.85, −1.08 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).
Cd1—N1 | 2.327 (4) | Cd1—I1 | 2.7523 (7) |
Cd1—N2 | 2.365 (4) | Cd1—I2 | 2.7635 (6) |
Cd1—O1 | 2.345 (5) |
Acknowledgements
We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.
References
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Recently, we reported the synthes and crystal structure of [CdBr2(4,4'-dmbpy)(DMSO)] (Shirvan & Haydari Dezfuli, 2012) [where 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine and DMSO is dimethyl sulfoxide]. 4,4'-Dimethyl-2,2'-bipyridine is a good bidentate ligand, and numerous complexes with 4,4'-dmbipy have been prepared, such as that of mercury (Kalateh et al., 2008; Yousefi et al., 2008), indium (Ahmadi et al., 2008), iron (Amani et al., 2009), platin (Hojjat Kashani et al., 2008), silver (Bellusci et al., 2008), gallium (Sofetis et al., 2006), copper (Willett et al., 2001), cadmium (Kalateh et al., 2010) and zinc (Alizadeh et al., 2010). Here, we report the synthesis and structure of the title compound.
In the title compound, (Fig. 1), the CdII atom is five-coordinated in a distorted trigonal-bipyramidal configuration by two N atoms from one 4,4'-dimethyl-2,2'-bipyridine, one O atom from one dimethylformamide and two I atoms. The Cd—N, Cd—I and Cd—O bond lengths and angles are collected in Table 1.
In the crystal structure, π-π contacts (Fig. 2) between the pyridine rings, Cg2—Cg2i and Cg2—Cg3ii [symmetry cods: (i) 1-X,-Y,-Z and (ii) 2-X,-Y,-Z, where Cg2 and Cg3 are centroids of the rings (N1/C1—C3/C5—C6) and (N2/C7—C9/C11—C12), respectively] stabilize the structure, with centroid-centroid distance of 3.666 (3) and 3.709 (4) Å.