Acta Cryst. (2012). E68, m1428 [ doi:10.1107/S1600536812044108 ]
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2N,N')bis(dicyanamido-N1)cadmiumIn the title compound, [Cd(C2N3)2(C10H8N2)2], the CdII ion is coordinated in a distorted octahedral environment by four N atoms from two chelating 2,2'-bipyridine ligands and two N atoms from two monodentate dicyanamide ligands. The dihedral angle between the mean planes of the two bipyridine ligands is 87.67 (6)°.
An aqueous solution (5 ml) of dca (0.178 g, 2 mmol) was mixed with an aqueous solution (5 ml) of Cd(NO3)2.4H2O (0.155 g, 0.5 mmol), at room temperature. The solution was stirred for 10 min. Then a methanolic solution (8 ml) containing bpy (0.312 g, 2 mmol) was added drop wise into the above solution. After the mixture was stirred for about 15 minutes at room temperature. It was filtrated and the filtrate was left for slow evaporation in air. Plate-shaped colorless crystals of [Cd(N(CN)2)2(bpy)2] were obtained from the mother liquor by slow evaporation at room temperature after two weeks.
H atoms were placed in calculated positions with C—H = 0.95Å and were included in the refinement with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
| [Cd(C2N3)2(C10H8N2)2] | F(000) = 1112 |
| Mr = 556.87 | Dx = 1.579 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 320 reflections |
| a = 9.5586 (3) Å | θ = 3.0–29.2° |
| b = 14.9260 (5) Å | µ = 0.97 mm−1 |
| c = 16.7007 (6) Å | T = 150 K |
| β = 100.521 (2)° | Plate, colourless |
| V = 2342.66 (14) Å3 | 0.30 × 0.16 × 0.03 mm |
| Z = 4 |
| Bruker SMART CCD diffractometer | 6309 independent reflections |
| Radiation source: fine-focus sealed tube | 5064 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.033 |
| φ and ω scans | θmax = 29.2°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −12→13 |
| Tmin = 0.760, Tmax = 0.972 | k = −19→20 |
| 25970 measured reflections | l = −22→22 |
| 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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.069 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0331P)2 + 0.4905P] where P = (Fo2 + 2Fc2)/3 |
| 6309 reflections | (Δ/σ)max = 0.003 |
| 316 parameters | Δρmax = 0.48 e Å−3 |
| 0 restraints | Δρmin = −0.39 e Å−3 |
| [Cd(C2N3)2(C10H8N2)2] | V = 2342.66 (14) Å3 |
| Mr = 556.87 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.5586 (3) Å | µ = 0.97 mm−1 |
| b = 14.9260 (5) Å | T = 150 K |
| c = 16.7007 (6) Å | 0.30 × 0.16 × 0.03 mm |
| β = 100.521 (2)° |
| Bruker SMART CCD diffractometer | 6309 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2008) | 5064 reflections with I > 2σ(I) |
| Tmin = 0.760, Tmax = 0.972 | Rint = 0.033 |
| 25970 measured reflections | θmax = 29.2° |
| R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
| wR(F2) = 0.069 | Δρmax = 0.48 e Å−3 |
| S = 1.01 | Δρmin = −0.39 e Å−3 |
| 6309 reflections | Absolute structure: ? |
| 316 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| Cd | 0.516014 (15) | 0.704173 (9) | 0.110929 (9) | 0.02649 (5) | |
| N1 | 0.41014 (17) | 0.82838 (11) | 0.02936 (11) | 0.0301 (4) | |
| C2 | 0.2810 (2) | 0.86215 (15) | 0.03317 (15) | 0.0377 (5) | |
| H2 | 0.2321 | 0.8397 | 0.0736 | 0.045* | |
| C3 | 0.2167 (2) | 0.92750 (15) | −0.01854 (16) | 0.0427 (6) | |
| H3 | 0.1255 | 0.9499 | −0.0139 | 0.051* | |
| C4 | 0.2872 (3) | 0.95978 (15) | −0.07727 (17) | 0.0458 (6) | |
| H4 | 0.2447 | 1.0044 | −0.1145 | 0.055* | |
| C5 | 0.4210 (2) | 0.92643 (14) | −0.08159 (15) | 0.0402 (5) | |
| H5 | 0.4719 | 0.9485 | −0.1213 | 0.048* | |
| C6 | 0.4796 (2) | 0.86051 (12) | −0.02727 (12) | 0.0278 (4) | |
| C7 | 0.6241 (2) | 0.82153 (13) | −0.02755 (13) | 0.0283 (4) | |
| C8 | 0.7115 (2) | 0.85346 (15) | −0.07896 (15) | 0.0407 (5) | |
| H8 | 0.6806 | 0.9009 | −0.1159 | 0.049* | |
| C9 | 0.8445 (3) | 0.81530 (16) | −0.07568 (18) | 0.0502 (7) | |
| H9 | 0.9060 | 0.8366 | −0.1102 | 0.060* | |
| C10 | 0.8865 (2) | 0.74695 (16) | −0.02259 (17) | 0.0447 (6) | |
| H10 | 0.9770 | 0.7196 | −0.0200 | 0.054* | |
| C11 | 0.7949 (2) | 0.71808 (14) | 0.02755 (15) | 0.0356 (5) | |
| H11 | 0.8244 | 0.6710 | 0.0651 | 0.043* | |
| N12 | 0.66591 (17) | 0.75460 (11) | 0.02463 (10) | 0.0271 (3) | |
| N13 | 0.61503 (18) | 0.80134 (11) | 0.21846 (11) | 0.0287 (4) | |
| C14 | 0.7419 (2) | 0.84160 (15) | 0.22300 (13) | 0.0348 (5) | |
| H14 | 0.7974 | 0.8280 | 0.1828 | 0.042* | |
| C15 | 0.7948 (2) | 0.90175 (16) | 0.28339 (15) | 0.0418 (5) | |
| H15 | 0.8852 | 0.9290 | 0.2852 | 0.050* | |
| C16 | 0.7134 (2) | 0.92151 (16) | 0.34129 (15) | 0.0424 (6) | |
| H16 | 0.7470 | 0.9629 | 0.3836 | 0.051* | |
| C17 | 0.5827 (2) | 0.88063 (14) | 0.33726 (13) | 0.0355 (5) | |
| H17 | 0.5255 | 0.8937 | 0.3767 | 0.043* | |
| C18 | 0.5361 (2) | 0.82024 (12) | 0.27498 (12) | 0.0264 (4) | |
| C19 | 0.3954 (2) | 0.77364 (12) | 0.26621 (12) | 0.0267 (4) | |
| C20 | 0.3047 (2) | 0.78768 (14) | 0.32058 (15) | 0.0397 (5) | |
| H20 | 0.3319 | 0.8264 | 0.3659 | 0.048* | |
| C21 | 0.1738 (3) | 0.74494 (16) | 0.30853 (16) | 0.0448 (6) | |
| H21 | 0.1094 | 0.7554 | 0.3447 | 0.054* | |
| C22 | 0.1381 (2) | 0.68769 (15) | 0.24420 (15) | 0.0392 (5) | |
| H22 | 0.0499 | 0.6566 | 0.2354 | 0.047* | |
| C23 | 0.2340 (2) | 0.67635 (15) | 0.19240 (14) | 0.0372 (5) | |
| H23 | 0.2093 | 0.6372 | 0.1472 | 0.045* | |
| N24 | 0.36027 (18) | 0.71798 (11) | 0.20291 (11) | 0.0309 (4) | |
| N25 | 0.6584 (2) | 0.59039 (14) | 0.16670 (14) | 0.0484 (5) | |
| C26 | 0.7001 (2) | 0.54121 (14) | 0.21884 (15) | 0.0354 (5) | |
| N27 | 0.73104 (19) | 0.48378 (13) | 0.27762 (12) | 0.0397 (4) | |
| C28 | 0.8637 (2) | 0.46549 (14) | 0.31152 (14) | 0.0353 (5) | |
| N29 | 0.9733 (2) | 0.44417 (17) | 0.34649 (15) | 0.0559 (6) | |
| N30 | 0.3634 (2) | 0.61331 (13) | 0.02748 (12) | 0.0435 (5) | |
| C31 | 0.2583 (2) | 0.59524 (13) | −0.01597 (14) | 0.0343 (5) | |
| N32 | 0.1425 (2) | 0.58623 (12) | −0.06940 (13) | 0.0432 (5) | |
| C33 | 0.0734 (2) | 0.51007 (15) | −0.08012 (14) | 0.0344 (5) | |
| N34 | 0.00240 (19) | 0.44904 (14) | −0.09561 (14) | 0.0459 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cd | 0.02787 (8) | 0.03095 (8) | 0.02186 (8) | −0.00212 (6) | 0.00773 (6) | −0.00153 (6) |
| N1 | 0.0289 (9) | 0.0325 (8) | 0.0294 (10) | 0.0026 (7) | 0.0065 (8) | −0.0025 (7) |
| C2 | 0.0318 (11) | 0.0428 (12) | 0.0401 (13) | 0.0052 (9) | 0.0111 (10) | −0.0044 (10) |
| C3 | 0.0324 (11) | 0.0428 (12) | 0.0510 (16) | 0.0109 (10) | 0.0020 (11) | −0.0049 (11) |
| C4 | 0.0445 (13) | 0.0374 (12) | 0.0509 (16) | 0.0089 (10) | −0.0035 (12) | 0.0056 (11) |
| C5 | 0.0443 (13) | 0.0370 (11) | 0.0388 (14) | 0.0041 (10) | 0.0062 (11) | 0.0084 (10) |
| C6 | 0.0314 (10) | 0.0264 (9) | 0.0249 (10) | −0.0007 (8) | 0.0031 (8) | −0.0048 (8) |
| C7 | 0.0321 (10) | 0.0272 (9) | 0.0269 (11) | −0.0009 (8) | 0.0090 (9) | −0.0036 (8) |
| C8 | 0.0475 (13) | 0.0372 (11) | 0.0422 (14) | 0.0033 (10) | 0.0212 (11) | 0.0083 (10) |
| C9 | 0.0491 (14) | 0.0480 (14) | 0.0626 (18) | 0.0002 (11) | 0.0347 (14) | 0.0078 (12) |
| C10 | 0.0346 (12) | 0.0457 (13) | 0.0589 (17) | 0.0044 (10) | 0.0223 (12) | −0.0011 (12) |
| C11 | 0.0329 (11) | 0.0353 (11) | 0.0410 (13) | 0.0065 (9) | 0.0133 (10) | 0.0006 (9) |
| N12 | 0.0288 (8) | 0.0284 (8) | 0.0255 (9) | 0.0024 (7) | 0.0088 (7) | −0.0001 (7) |
| N13 | 0.0280 (8) | 0.0356 (9) | 0.0227 (9) | −0.0041 (7) | 0.0049 (7) | −0.0012 (7) |
| C14 | 0.0297 (11) | 0.0466 (12) | 0.0283 (12) | −0.0080 (9) | 0.0057 (9) | −0.0051 (10) |
| C15 | 0.0361 (12) | 0.0536 (13) | 0.0350 (13) | −0.0155 (10) | 0.0051 (10) | −0.0047 (11) |
| C16 | 0.0421 (13) | 0.0481 (13) | 0.0354 (14) | −0.0117 (10) | 0.0034 (11) | −0.0138 (11) |
| C17 | 0.0369 (11) | 0.0419 (11) | 0.0283 (12) | −0.0028 (9) | 0.0074 (9) | −0.0074 (9) |
| C18 | 0.0299 (10) | 0.0275 (9) | 0.0217 (10) | 0.0009 (8) | 0.0043 (8) | 0.0017 (8) |
| C19 | 0.0301 (10) | 0.0269 (9) | 0.0239 (10) | 0.0005 (8) | 0.0072 (8) | 0.0025 (8) |
| C20 | 0.0425 (13) | 0.0434 (12) | 0.0376 (13) | −0.0101 (10) | 0.0188 (11) | −0.0136 (10) |
| C21 | 0.0454 (13) | 0.0496 (13) | 0.0473 (16) | −0.0104 (11) | 0.0290 (12) | −0.0103 (12) |
| C22 | 0.0318 (11) | 0.0450 (12) | 0.0436 (14) | −0.0107 (9) | 0.0145 (10) | −0.0046 (10) |
| C23 | 0.0367 (12) | 0.0444 (11) | 0.0326 (12) | −0.0116 (10) | 0.0118 (10) | −0.0085 (10) |
| N24 | 0.0298 (9) | 0.0382 (9) | 0.0261 (9) | −0.0071 (7) | 0.0087 (7) | −0.0058 (7) |
| N25 | 0.0481 (12) | 0.0464 (11) | 0.0526 (14) | 0.0119 (9) | 0.0146 (11) | 0.0123 (10) |
| C26 | 0.0342 (11) | 0.0325 (10) | 0.0420 (14) | 0.0008 (9) | 0.0133 (10) | −0.0061 (10) |
| N27 | 0.0353 (10) | 0.0417 (10) | 0.0427 (12) | −0.0015 (8) | 0.0083 (9) | 0.0088 (9) |
| C28 | 0.0379 (12) | 0.0388 (11) | 0.0310 (12) | −0.0051 (9) | 0.0110 (10) | −0.0014 (9) |
| N29 | 0.0376 (12) | 0.0804 (16) | 0.0485 (14) | 0.0001 (11) | 0.0051 (10) | 0.0099 (13) |
| N30 | 0.0526 (12) | 0.0437 (10) | 0.0341 (11) | −0.0161 (10) | 0.0079 (10) | −0.0037 (9) |
| C31 | 0.0452 (13) | 0.0306 (10) | 0.0307 (12) | −0.0054 (9) | 0.0166 (11) | −0.0002 (9) |
| N32 | 0.0390 (11) | 0.0396 (10) | 0.0486 (13) | −0.0037 (8) | 0.0019 (10) | 0.0130 (9) |
| C33 | 0.0281 (10) | 0.0406 (11) | 0.0334 (12) | 0.0036 (9) | 0.0028 (9) | 0.0059 (10) |
| N34 | 0.0316 (10) | 0.0450 (11) | 0.0561 (15) | 0.0024 (9) | −0.0052 (10) | −0.0059 (10) |
| Cd—N25 | 2.267 (2) | N13—C14 | 1.343 (3) |
| Cd—N30 | 2.273 (2) | C14—C15 | 1.376 (3) |
| Cd—N12 | 2.3347 (15) | C14—H14 | 0.9500 |
| Cd—N24 | 2.3352 (16) | C15—C16 | 1.379 (3) |
| Cd—N13 | 2.3672 (17) | C15—H15 | 0.9500 |
| Cd—N1 | 2.4111 (17) | C16—C17 | 1.381 (3) |
| N1—C6 | 1.339 (3) | C16—H16 | 0.9500 |
| N1—C2 | 1.345 (3) | C17—C18 | 1.387 (3) |
| C2—C3 | 1.372 (3) | C17—H17 | 0.9500 |
| C2—H2 | 0.9500 | C18—C19 | 1.497 (3) |
| C3—C4 | 1.374 (4) | C19—N24 | 1.338 (3) |
| C3—H3 | 0.9500 | C19—C20 | 1.381 (3) |
| C4—C5 | 1.387 (3) | C20—C21 | 1.387 (3) |
| C4—H4 | 0.9500 | C20—H20 | 0.9500 |
| C5—C6 | 1.385 (3) | C21—C22 | 1.366 (3) |
| C5—H5 | 0.9500 | C21—H21 | 0.9500 |
| C6—C7 | 1.500 (3) | C22—C23 | 1.381 (3) |
| C7—N12 | 1.338 (3) | C22—H22 | 0.9500 |
| C7—C8 | 1.388 (3) | C23—N24 | 1.341 (3) |
| C8—C9 | 1.385 (3) | C23—H23 | 0.9500 |
| C8—H8 | 0.9500 | N25—C26 | 1.153 (3) |
| C9—C10 | 1.363 (4) | C26—N27 | 1.296 (3) |
| C9—H9 | 0.9500 | N27—C28 | 1.320 (3) |
| C10—C11 | 1.386 (3) | C28—N29 | 1.147 (3) |
| C10—H10 | 0.9500 | N30—C31 | 1.159 (3) |
| C11—N12 | 1.341 (3) | C31—N32 | 1.296 (3) |
| C11—H11 | 0.9500 | N32—C33 | 1.311 (3) |
| N13—C18 | 1.342 (2) | C33—N34 | 1.137 (3) |
| N25—Cd—N30 | 94.29 (8) | C7—N12—C11 | 119.39 (17) |
| N25—Cd—N12 | 96.04 (6) | C7—N12—Cd | 119.90 (12) |
| N30—Cd—N12 | 102.20 (6) | C11—N12—Cd | 120.70 (14) |
| N25—Cd—N24 | 101.70 (7) | C18—N13—C14 | 118.97 (18) |
| N30—Cd—N24 | 92.35 (6) | C18—N13—Cd | 117.65 (13) |
| N12—Cd—N24 | 156.12 (6) | C14—N13—Cd | 123.28 (14) |
| N25—Cd—N13 | 91.17 (7) | N13—C14—C15 | 122.7 (2) |
| N30—Cd—N13 | 162.47 (6) | N13—C14—H14 | 118.6 |
| N12—Cd—N13 | 93.75 (6) | C15—C14—H14 | 118.6 |
| N24—Cd—N13 | 70.21 (6) | C14—C15—C16 | 118.3 (2) |
| N25—Cd—N1 | 165.14 (6) | C14—C15—H15 | 120.8 |
| N30—Cd—N1 | 87.49 (7) | C16—C15—H15 | 120.8 |
| N12—Cd—N1 | 69.20 (5) | C17—C16—C15 | 119.5 (2) |
| N24—Cd—N1 | 92.96 (6) | C17—C16—H16 | 120.2 |
| N13—Cd—N1 | 91.49 (6) | C15—C16—H16 | 120.2 |
| C6—N1—C2 | 118.44 (19) | C16—C17—C18 | 119.20 (19) |
| C6—N1—Cd | 117.60 (13) | C16—C17—H17 | 120.4 |
| C2—N1—Cd | 123.74 (14) | C18—C17—H17 | 120.4 |
| N1—C2—C3 | 123.1 (2) | N13—C18—C17 | 121.26 (18) |
| N1—C2—H2 | 118.4 | N13—C18—C19 | 116.36 (17) |
| C3—C2—H2 | 118.4 | C17—C18—C19 | 122.38 (18) |
| C2—C3—C4 | 118.5 (2) | N24—C19—C20 | 121.09 (19) |
| C2—C3—H3 | 120.8 | N24—C19—C18 | 117.21 (17) |
| C4—C3—H3 | 120.8 | C20—C19—C18 | 121.70 (19) |
| C3—C4—C5 | 119.2 (2) | C19—C20—C21 | 119.6 (2) |
| C3—C4—H4 | 120.4 | C19—C20—H20 | 120.2 |
| C5—C4—H4 | 120.4 | C21—C20—H20 | 120.2 |
| C6—C5—C4 | 119.2 (2) | C22—C21—C20 | 119.4 (2) |
| C6—C5—H5 | 120.4 | C22—C21—H21 | 120.3 |
| C4—C5—H5 | 120.4 | C20—C21—H21 | 120.3 |
| N1—C6—C5 | 121.58 (19) | C21—C22—C23 | 118.0 (2) |
| N1—C6—C7 | 116.02 (18) | C21—C22—H22 | 121.0 |
| C5—C6—C7 | 122.40 (19) | C23—C22—H22 | 121.0 |
| N12—C7—C8 | 121.14 (19) | N24—C23—C22 | 123.1 (2) |
| N12—C7—C6 | 116.98 (17) | N24—C23—H23 | 118.4 |
| C8—C7—C6 | 121.88 (19) | C22—C23—H23 | 118.4 |
| C9—C8—C7 | 119.1 (2) | C19—N24—C23 | 118.77 (17) |
| C9—C8—H8 | 120.4 | C19—N24—Cd | 118.43 (12) |
| C7—C8—H8 | 120.4 | C23—N24—Cd | 122.69 (14) |
| C10—C9—C8 | 119.5 (2) | C26—N25—Cd | 152.39 (18) |
| C10—C9—H9 | 120.2 | N25—C26—N27 | 173.1 (2) |
| C8—C9—H9 | 120.2 | C26—N27—C28 | 122.02 (19) |
| C9—C10—C11 | 118.8 (2) | N29—C28—N27 | 172.9 (2) |
| C9—C10—H10 | 120.6 | C31—N30—Cd | 155.35 (19) |
| C11—C10—H10 | 120.6 | N30—C31—N32 | 171.7 (2) |
| N12—C11—C10 | 122.0 (2) | C31—N32—C33 | 122.00 (19) |
| N12—C11—H11 | 119.0 | N34—C33—N32 | 172.3 (2) |
| C10—C11—H11 | 119.0 |
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![[Figure 1]](./lh5540fig1thm.gif)
Coordination polymers containing dicyanamide [dca-, N(CN)2-] have gained attention in the last decade due to their versatile binding modes where the three possible donor sites allow monodentate to pentadentate binding to the metal centre (Mal et al., 2006; Wang et al., 2012; Luo et al. 2002). Herein, we present the crystal structure of the title complex.
The molecular structure of the title compound is shown in Fig. 1. The CdII ion is coordinated by six N atoms, two of which are from monodentate dca ligands and four N atoms are from from two chelating bpy ligands. The coordination geometry is distorted octahedral. The Cd—Nbpy and Cd—Ndca bond distances are comparable with a previously reported cadmium-dca-bpy complex (Luo et al., 2002). The Cd—Ndicyanamido bond lengths are slightly shorter than the Cd—Nbipyridine lengths. The crystal structure of the Mn(II) analog of the title compound has been published previously (Wang et al., 2012).