metal-organic compounds
Di-μ-bromido-bis[bromido(4,7-diphenyl-1,10-phenanthroline-κ2N,N′)cadmium]
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
The title compound, [Cd2Br4(C24H16N2)2], consists of a centrosymmetric dimeric unit in which two Br atoms bridge two CdII atoms, forming a four-membered ring. A terminal Br atom and a bidentate chelating 4,7-diphenyl-1,10-phenanthroline ligand complete a square-pyramidal geometry for the CdII atom. In the crystal, C—H⋯Br hydrogen bonds and π–π contacts between the pyridine and phenyl rings [centroid–centroid distances = 3.704 (4) and 3.715 (4) Å] lead to a three-dimensional supramolecular structure.
Related literature
For related structures, see: Abedi et al. (2012); Ahmadi et al. (2008); Alizadeh et al. (2010); Chesnut et al. (2001); Gaballa et al. (2003); 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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812045928/hy2601sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045928/hy2601Isup2.hkl
For the preparation of the title compound, a solution of Ph2phen (0.44 g, 1.33 mmol) in methanol (10 ml) was added to a solution of CdBr2.4H2O (0.46 g, 1.33 mmol) in methanol (10 ml) at room temperature. Crystals suitable for X-ray diffraction experiment were obtained by methanol diffusion into a colorless solution in DMSO after one week (yield: 0.62 g, 77.1%).
All H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and 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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).[Cd2Br4(C24H16N2)2] | F(000) = 1168 |
Mr = 1209.20 | Dx = 1.875 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 12072 reflections |
a = 10.1704 (4) Å | θ = 2.4–26.0° |
b = 12.4702 (5) Å | µ = 4.76 mm−1 |
c = 17.3444 (7) Å | T = 120 K |
β = 103.187 (3)° | Prism, colorless |
V = 2141.73 (15) Å3 | 0.25 × 0.18 × 0.15 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 4200 independent reflections |
Radiation source: fine-focus sealed tube | 3248 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.090 |
ϕ and ω scans | θmax = 26.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −12→9 |
Tmin = 0.385, Tmax = 0.502 | k = −15→15 |
12072 measured reflections | l = −21→21 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0692P)2] where P = (Fo2 + 2Fc2)/3 |
4200 reflections | (Δ/σ)max = 0.005 |
262 parameters | Δρmax = 1.15 e Å−3 |
0 restraints | Δρmin = −1.05 e Å−3 |
[Cd2Br4(C24H16N2)2] | V = 2141.73 (15) Å3 |
Mr = 1209.20 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.1704 (4) Å | µ = 4.76 mm−1 |
b = 12.4702 (5) Å | T = 120 K |
c = 17.3444 (7) Å | 0.25 × 0.18 × 0.15 mm |
β = 103.187 (3)° |
Bruker APEXII CCD diffractometer | 4200 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 3248 reflections with I > 2σ(I) |
Tmin = 0.385, Tmax = 0.502 | Rint = 0.090 |
12072 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.05 | Δρmax = 1.15 e Å−3 |
4200 reflections | Δρmin = −1.05 e Å−3 |
262 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 | 0.3033 (7) | 0.7552 (6) | 0.0038 (4) | 0.0220 (15) | |
H1 | 0.2143 | 0.7327 | −0.0137 | 0.026* | |
C2 | 0.4054 (7) | 0.6893 (6) | −0.0089 (4) | 0.0212 (15) | |
H2 | 0.3842 | 0.6233 | −0.0336 | 0.025* | |
C3 | 0.5378 (7) | 0.7205 (5) | 0.0147 (4) | 0.0198 (14) | |
C4 | 0.6478 (8) | 0.6468 (5) | 0.0047 (5) | 0.0230 (15) | |
C5 | 0.6445 (9) | 0.6043 (6) | −0.0702 (5) | 0.0342 (19) | |
H5 | 0.5770 | 0.6250 | −0.1134 | 0.041* | |
C6 | 0.7429 (9) | 0.5306 (7) | −0.0800 (6) | 0.044 (2) | |
H6 | 0.7435 | 0.5048 | −0.1302 | 0.052* | |
C7 | 0.8396 (9) | 0.4960 (6) | −0.0150 (6) | 0.039 (2) | |
H7 | 0.9039 | 0.4457 | −0.0212 | 0.047* | |
C8 | 0.8401 (8) | 0.5363 (7) | 0.0590 (6) | 0.0329 (18) | |
H8 | 0.9037 | 0.5117 | 0.1028 | 0.040* | |
C9 | 0.7462 (8) | 0.6139 (6) | 0.0690 (5) | 0.0281 (17) | |
H9 | 0.7500 | 0.6432 | 0.1187 | 0.034* | |
C10 | 0.5663 (7) | 0.8236 (5) | 0.0511 (4) | 0.0171 (14) | |
C11 | 0.6978 (8) | 0.8691 (6) | 0.0725 (4) | 0.0206 (15) | |
H11 | 0.7700 | 0.8317 | 0.0608 | 0.025* | |
C12 | 0.7213 (7) | 0.9657 (6) | 0.1095 (4) | 0.0187 (14) | |
H12 | 0.8079 | 0.9947 | 0.1206 | 0.022* | |
C13 | 0.6142 (7) | 1.0227 (5) | 0.1312 (4) | 0.0163 (13) | |
C14 | 0.6353 (8) | 1.1181 (6) | 0.1777 (4) | 0.0226 (15) | |
C15 | 0.7704 (7) | 1.1668 (5) | 0.2081 (4) | 0.0195 (14) | |
C16 | 0.8805 (9) | 1.1070 (6) | 0.2449 (4) | 0.0303 (18) | |
H16 | 0.8708 | 1.0338 | 0.2523 | 0.036* | |
C17 | 1.0068 (8) | 1.1553 (7) | 0.2711 (5) | 0.0318 (19) | |
H17 | 1.0812 | 1.1140 | 0.2948 | 0.038* | |
C18 | 1.0212 (9) | 1.2650 (7) | 0.2618 (5) | 0.037 (2) | |
H18 | 1.1052 | 1.2975 | 0.2789 | 0.045* | |
C19 | 0.9106 (9) | 1.3248 (7) | 0.2272 (4) | 0.0301 (18) | |
H19 | 0.9203 | 1.3982 | 0.2204 | 0.036* | |
C20 | 0.7865 (7) | 1.2787 (6) | 0.2025 (4) | 0.0229 (15) | |
H20 | 0.7118 | 1.3214 | 0.1817 | 0.027* | |
C21 | 0.5205 (8) | 1.1675 (6) | 0.1945 (5) | 0.0261 (16) | |
H21 | 0.5298 | 1.2292 | 0.2254 | 0.031* | |
C22 | 0.3948 (7) | 1.1245 (6) | 0.1654 (4) | 0.0236 (16) | |
H22 | 0.3213 | 1.1601 | 0.1770 | 0.028* | |
C23 | 0.4797 (7) | 0.9847 (5) | 0.1065 (4) | 0.0159 (13) | |
C24 | 0.4563 (7) | 0.8838 (5) | 0.0639 (4) | 0.0172 (14) | |
N1 | 0.3274 (6) | 0.8502 (5) | 0.0403 (3) | 0.0190 (12) | |
N2 | 0.3701 (6) | 1.0356 (5) | 0.1218 (3) | 0.0197 (12) | |
Cd1 | 0.15894 (5) | 0.95338 (4) | 0.07604 (3) | 0.01781 (15) | |
Br1 | 0.10996 (9) | 0.87751 (7) | 0.20336 (5) | 0.0309 (2) | |
Br2 | 0.03037 (7) | 1.14002 (5) | 0.04404 (4) | 0.02161 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.020 (4) | 0.023 (4) | 0.026 (4) | −0.002 (3) | 0.011 (3) | 0.000 (3) |
C2 | 0.019 (3) | 0.024 (4) | 0.024 (3) | −0.001 (3) | 0.012 (3) | −0.008 (3) |
C3 | 0.025 (4) | 0.016 (3) | 0.018 (3) | 0.000 (3) | 0.005 (3) | 0.003 (3) |
C4 | 0.024 (4) | 0.015 (3) | 0.032 (4) | −0.004 (3) | 0.011 (3) | −0.004 (3) |
C5 | 0.040 (5) | 0.024 (4) | 0.038 (5) | −0.004 (4) | 0.010 (4) | −0.012 (4) |
C6 | 0.038 (5) | 0.033 (5) | 0.062 (6) | −0.001 (4) | 0.017 (4) | −0.022 (4) |
C7 | 0.031 (4) | 0.018 (4) | 0.079 (7) | −0.002 (3) | 0.037 (5) | −0.012 (4) |
C8 | 0.016 (3) | 0.031 (4) | 0.055 (5) | 0.001 (3) | 0.017 (3) | 0.008 (4) |
C9 | 0.026 (4) | 0.025 (4) | 0.040 (4) | 0.002 (3) | 0.023 (4) | 0.002 (3) |
C10 | 0.019 (3) | 0.016 (3) | 0.016 (3) | 0.002 (3) | 0.004 (3) | 0.001 (3) |
C11 | 0.027 (4) | 0.022 (3) | 0.015 (3) | 0.002 (3) | 0.010 (3) | −0.003 (3) |
C12 | 0.018 (3) | 0.021 (3) | 0.016 (3) | −0.005 (3) | 0.003 (3) | 0.001 (3) |
C13 | 0.017 (3) | 0.021 (3) | 0.015 (3) | 0.002 (3) | 0.012 (3) | 0.004 (3) |
C14 | 0.027 (4) | 0.017 (3) | 0.022 (3) | −0.002 (3) | 0.001 (3) | −0.002 (3) |
C15 | 0.026 (4) | 0.017 (3) | 0.017 (3) | 0.001 (3) | 0.007 (3) | −0.004 (3) |
C16 | 0.044 (5) | 0.026 (4) | 0.018 (4) | 0.002 (4) | 0.002 (3) | −0.005 (3) |
C17 | 0.024 (4) | 0.047 (5) | 0.023 (4) | 0.006 (4) | 0.002 (3) | −0.016 (4) |
C18 | 0.034 (5) | 0.046 (5) | 0.034 (4) | −0.016 (4) | 0.014 (4) | −0.024 (4) |
C19 | 0.038 (5) | 0.032 (4) | 0.023 (4) | −0.010 (4) | 0.011 (3) | −0.008 (3) |
C20 | 0.023 (4) | 0.025 (4) | 0.022 (3) | 0.002 (3) | 0.008 (3) | −0.006 (3) |
C21 | 0.024 (4) | 0.021 (4) | 0.033 (4) | 0.006 (3) | 0.006 (3) | −0.008 (3) |
C22 | 0.020 (4) | 0.026 (4) | 0.031 (4) | 0.006 (3) | 0.020 (3) | −0.001 (3) |
C23 | 0.020 (3) | 0.016 (3) | 0.013 (3) | 0.001 (3) | 0.007 (3) | 0.002 (2) |
C24 | 0.023 (4) | 0.014 (3) | 0.013 (3) | 0.001 (3) | 0.002 (3) | 0.001 (3) |
N1 | 0.018 (3) | 0.022 (3) | 0.019 (3) | −0.002 (2) | 0.007 (2) | 0.001 (2) |
N2 | 0.019 (3) | 0.023 (3) | 0.023 (3) | 0.005 (3) | 0.016 (2) | 0.003 (3) |
Cd1 | 0.0164 (3) | 0.0199 (3) | 0.0193 (2) | 0.0026 (2) | 0.00858 (18) | 0.0045 (2) |
Br1 | 0.0369 (4) | 0.0325 (4) | 0.0291 (4) | 0.0053 (3) | 0.0195 (3) | 0.0146 (3) |
Br2 | 0.0191 (3) | 0.0189 (3) | 0.0267 (4) | 0.0035 (3) | 0.0050 (3) | 0.0001 (3) |
C1—N1 | 1.339 (9) | C14—C21 | 1.409 (11) |
C1—C2 | 1.381 (10) | C14—C15 | 1.484 (10) |
C1—H1 | 0.9300 | C15—C16 | 1.375 (11) |
C2—C3 | 1.372 (10) | C15—C20 | 1.411 (10) |
C2—H2 | 0.9300 | C16—C17 | 1.398 (12) |
C3—C10 | 1.432 (9) | C16—H16 | 0.9300 |
C3—C4 | 1.489 (10) | C17—C18 | 1.389 (13) |
C4—C9 | 1.379 (11) | C17—H17 | 0.9300 |
C4—C5 | 1.396 (11) | C18—C19 | 1.369 (13) |
C5—C6 | 1.398 (12) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.365 (11) |
C6—C7 | 1.385 (14) | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.377 (13) | C21—C22 | 1.371 (11) |
C7—H7 | 0.9300 | C21—H21 | 0.9300 |
C8—C9 | 1.398 (11) | C22—N2 | 1.333 (9) |
C8—H8 | 0.9300 | C22—H22 | 0.9300 |
C9—H9 | 0.9300 | C23—N2 | 1.361 (9) |
C10—C24 | 1.406 (10) | C23—C24 | 1.452 (9) |
C10—C11 | 1.423 (10) | C24—N1 | 1.349 (9) |
C11—C12 | 1.361 (9) | Cd1—N1 | 2.336 (6) |
C11—H11 | 0.9300 | Cd1—N2 | 2.349 (6) |
C12—C13 | 1.421 (10) | Cd1—Br1 | 2.5537 (9) |
C12—H12 | 0.9300 | Cd1—Br2 | 2.6653 (8) |
C13—C23 | 1.418 (9) | Cd1—Br2i | 2.7518 (9) |
C13—C14 | 1.426 (9) | ||
N1—C1—C2 | 122.6 (7) | C15—C16—C17 | 120.5 (8) |
N1—C1—H1 | 118.7 | C15—C16—H16 | 119.8 |
C2—C1—H1 | 118.7 | C17—C16—H16 | 119.8 |
C3—C2—C1 | 120.4 (7) | C18—C17—C16 | 120.1 (8) |
C3—C2—H2 | 119.8 | C18—C17—H17 | 120.0 |
C1—C2—H2 | 119.8 | C16—C17—H17 | 120.0 |
C2—C3—C10 | 118.2 (7) | C19—C18—C17 | 119.3 (8) |
C2—C3—C4 | 120.2 (6) | C19—C18—H18 | 120.4 |
C10—C3—C4 | 121.6 (6) | C17—C18—H18 | 120.4 |
C9—C4—C5 | 119.9 (7) | C20—C19—C18 | 121.1 (8) |
C9—C4—C3 | 121.0 (7) | C20—C19—H19 | 119.4 |
C5—C4—C3 | 118.9 (7) | C18—C19—H19 | 119.4 |
C4—C5—C6 | 119.8 (8) | C19—C20—C15 | 120.6 (7) |
C4—C5—H5 | 120.1 | C19—C20—H20 | 119.7 |
C6—C5—H5 | 120.1 | C15—C20—H20 | 119.7 |
C7—C6—C5 | 120.0 (9) | C22—C21—C14 | 120.0 (7) |
C7—C6—H6 | 120.0 | C22—C21—H21 | 120.0 |
C5—C6—H6 | 120.0 | C14—C21—H21 | 120.0 |
C8—C7—C6 | 119.8 (8) | N2—C22—C21 | 125.0 (7) |
C8—C7—H7 | 120.1 | N2—C22—H22 | 117.5 |
C6—C7—H7 | 120.1 | C21—C22—H22 | 117.5 |
C7—C8—C9 | 120.7 (8) | N2—C23—C13 | 124.2 (6) |
C7—C8—H8 | 119.7 | N2—C23—C24 | 117.2 (6) |
C9—C8—H8 | 119.7 | C13—C23—C24 | 118.6 (6) |
C4—C9—C8 | 119.7 (8) | N1—C24—C10 | 122.7 (6) |
C4—C9—H9 | 120.1 | N1—C24—C23 | 117.3 (6) |
C8—C9—H9 | 120.1 | C10—C24—C23 | 120.0 (6) |
C24—C10—C11 | 118.7 (6) | C1—N1—C24 | 118.6 (6) |
C24—C10—C3 | 117.4 (6) | C1—N1—Cd1 | 123.1 (5) |
C11—C10—C3 | 123.8 (7) | C24—N1—Cd1 | 118.0 (4) |
C12—C11—C10 | 122.0 (7) | C22—N2—C23 | 116.2 (6) |
C12—C11—H11 | 119.0 | C22—N2—Cd1 | 126.5 (5) |
C10—C11—H11 | 119.0 | C23—N2—Cd1 | 117.2 (4) |
C11—C12—C13 | 120.4 (6) | N1—Cd1—N2 | 70.2 (2) |
C11—C12—H12 | 119.8 | N1—Cd1—Br1 | 108.95 (14) |
C13—C12—H12 | 119.8 | N2—Cd1—Br1 | 102.32 (14) |
C23—C13—C12 | 119.8 (6) | N1—Cd1—Br2 | 141.29 (14) |
C23—C13—C14 | 117.4 (6) | N2—Cd1—Br2 | 93.23 (14) |
C12—C13—C14 | 122.8 (6) | Br1—Cd1—Br2 | 108.68 (3) |
C21—C14—C13 | 117.2 (7) | N1—Cd1—Br2i | 89.71 (14) |
C21—C14—C15 | 119.5 (6) | N2—Cd1—Br2i | 150.28 (14) |
C13—C14—C15 | 123.3 (7) | Br1—Cd1—Br2i | 104.89 (3) |
C16—C15—C20 | 118.3 (7) | Br2—Cd1—Br2i | 89.24 (3) |
C16—C15—C14 | 122.2 (7) | Cd1—Br2—Cd1i | 90.76 (3) |
C20—C15—C14 | 119.5 (7) | ||
N1—C1—C2—C3 | −1.2 (11) | C14—C13—C23—N2 | 2.6 (10) |
C1—C2—C3—C10 | −1.3 (10) | C12—C13—C23—C24 | 4.2 (9) |
C1—C2—C3—C4 | 176.8 (7) | C14—C13—C23—C24 | −175.7 (6) |
C2—C3—C4—C9 | −120.8 (8) | C11—C10—C24—N1 | 175.1 (6) |
C10—C3—C4—C9 | 57.2 (10) | C3—C10—C24—N1 | −2.9 (10) |
C2—C3—C4—C5 | 54.2 (10) | C11—C10—C24—C23 | −7.1 (9) |
C10—C3—C4—C5 | −127.8 (8) | C3—C10—C24—C23 | 174.8 (6) |
C9—C4—C5—C6 | −1.6 (12) | N2—C23—C24—N1 | 2.3 (9) |
C3—C4—C5—C6 | −176.7 (7) | C13—C23—C24—N1 | −179.2 (6) |
C4—C5—C6—C7 | 3.1 (13) | N2—C23—C24—C10 | −175.6 (6) |
C5—C6—C7—C8 | −1.5 (13) | C13—C23—C24—C10 | 2.9 (9) |
C6—C7—C8—C9 | −1.6 (12) | C2—C1—N1—C24 | 1.6 (10) |
C5—C4—C9—C8 | −1.5 (11) | C2—C1—N1—Cd1 | −172.4 (5) |
C3—C4—C9—C8 | 173.5 (7) | C10—C24—N1—C1 | 0.6 (10) |
C7—C8—C9—C4 | 3.1 (11) | C23—C24—N1—C1 | −177.3 (6) |
C2—C3—C10—C24 | 3.2 (9) | C10—C24—N1—Cd1 | 174.8 (5) |
C4—C3—C10—C24 | −174.8 (6) | C23—C24—N1—Cd1 | −3.0 (8) |
C2—C3—C10—C11 | −174.7 (7) | C21—C22—N2—C23 | 0.7 (10) |
C4—C3—C10—C11 | 7.2 (10) | C21—C22—N2—Cd1 | 176.5 (6) |
C24—C10—C11—C12 | 4.4 (10) | C13—C23—N2—C22 | −2.6 (9) |
C3—C10—C11—C12 | −177.7 (6) | C24—C23—N2—C22 | 175.7 (6) |
C10—C11—C12—C13 | 2.7 (10) | C13—C23—N2—Cd1 | −178.8 (5) |
C11—C12—C13—C23 | −7.1 (9) | C24—C23—N2—Cd1 | −0.5 (7) |
C11—C12—C13—C14 | 172.8 (6) | C1—N1—Cd1—N2 | 176.0 (6) |
C23—C13—C14—C21 | −0.7 (9) | C24—N1—Cd1—N2 | 2.0 (5) |
C12—C13—C14—C21 | 179.4 (7) | C1—N1—Cd1—Br1 | 79.3 (5) |
C23—C13—C14—C15 | 179.6 (6) | C24—N1—Cd1—Br1 | −94.7 (5) |
C12—C13—C14—C15 | −0.3 (10) | C1—N1—Cd1—Br2 | −114.7 (5) |
C21—C14—C15—C16 | 133.3 (8) | C24—N1—Cd1—Br2 | 71.2 (5) |
C13—C14—C15—C16 | −47.1 (11) | C1—N1—Cd1—Br2i | −26.3 (5) |
C21—C14—C15—C20 | −44.0 (10) | C24—N1—Cd1—Br2i | 159.7 (5) |
C13—C14—C15—C20 | 135.7 (7) | C22—N2—Cd1—N1 | −176.5 (6) |
C20—C15—C16—C17 | −4.2 (11) | C23—N2—Cd1—N1 | −0.7 (4) |
C14—C15—C16—C17 | 178.5 (7) | C22—N2—Cd1—Br1 | −70.6 (6) |
C15—C16—C17—C18 | 1.5 (12) | C23—N2—Cd1—Br1 | 105.2 (4) |
C16—C17—C18—C19 | 0.3 (12) | C22—N2—Cd1—Br2 | 39.3 (6) |
C17—C18—C19—C20 | 0.6 (12) | C23—N2—Cd1—Br2 | −144.9 (4) |
C18—C19—C20—C15 | −3.4 (11) | C22—N2—Cd1—Br2i | 133.5 (5) |
C16—C15—C20—C19 | 5.2 (11) | C23—N2—Cd1—Br2i | −50.7 (6) |
C14—C15—C20—C19 | −177.5 (7) | N1—Cd1—Br2—Cd1i | 88.6 (2) |
C13—C14—C21—C22 | −1.0 (11) | N2—Cd1—Br2—Cd1i | 150.36 (14) |
C15—C14—C21—C22 | 178.7 (7) | Br1—Cd1—Br2—Cd1i | −105.47 (3) |
C14—C21—C22—N2 | 1.1 (12) | Br2i—Cd1—Br2—Cd1i | 0.0 |
C12—C13—C23—N2 | −177.5 (6) |
Symmetry code: (i) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···Br2i | 0.93 | 2.90 | 3.554 (7) | 129 |
C21—H21···Br1ii | 0.93 | 2.79 | 3.582 (8) | 144 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cd2Br4(C24H16N2)2] |
Mr | 1209.20 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 120 |
a, b, c (Å) | 10.1704 (4), 12.4702 (5), 17.3444 (7) |
β (°) | 103.187 (3) |
V (Å3) | 2141.73 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 4.76 |
Crystal size (mm) | 0.25 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.385, 0.502 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12072, 4200, 3248 |
Rint | 0.090 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.129, 1.05 |
No. of reflections | 4200 |
No. of parameters | 262 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.15, −1.05 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2006).
Cd1—N1 | 2.336 (6) | Cd1—Br2 | 2.6653 (8) |
Cd1—N2 | 2.349 (6) | Cd1—Br2i | 2.7518 (9) |
Cd1—Br1 | 2.5537 (9) |
Symmetry code: (i) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···Br2i | 0.93 | 2.90 | 3.554 (7) | 129 |
C21—H21···Br1ii | 0.93 | 2.79 | 3.582 (8) | 144 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, y+1/2, −z+1/2. |
Acknowledgements
We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
4,7-Diphenyl-1,10-phenanthroline (Ph2phen) is a good bidentate ligand, and numerous complexes with Ph2phen have been prepared, such as that of mercury (Alizadeh et al., 2010; Yousefi et al., 2008), gold (Ahmadi et al., 2008), indium (Abedi et al., 2012), copper (Chesnut et al., 2001) and platinum (Gaballa et al., 2003). Here, we report the synthesis and structure of the title compound.
The structure of the title compound (Fig. 1) consists of a centrosymmetric dimeric unit, [Cd2Br4(Ph2phen)2], in which two Br atoms bridge two CdII atoms, forming a four-membered ring; a terminal Br atom and a bidentate chelating Ph2phen complete a five coordination (Table 1). In the crystal structure, intermolecular C—H···Br hydrogen bonds (Table 2) and π–π contacts (Fig. 2) between the pyridine and phenyl rings, Cg3···Cg4i and Cg6···Cg6i [symmetry code: (i) 1-x, 2-y, -z, Cg3, Cg4 and Cg6 are the centroids of the rings N1/C1–C3/C10/C24, N2/C13–C14/C21–C23 and C10–C13/C23–C24, respectively], with centroid–centroid distances of 3.704 (4) and 3.715 (4) Å, stabilize the structure.