Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043255/hy2081sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043255/hy2081Isup2.hkl |
CCDC reference: 663580
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.042
- wR factor = 0.091
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 300 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.92 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C28 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C27 PLAT480_ALERT_4_C Long H...A H-Bond Reported H16A .. CL2 .. 2.84 Ang.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C29 H34 Cd1 Cl2 N4 Atom count from _chemical_formula_moiety:C2 H3 N1 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1 (2) 2.11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For related literature, see: Fan et al. (2004); Tang & Vanslyke (1987); Wang (2001).
The title complex was synthesized according to the literature procedure (Fan et al., 2004). To a solution of 2,6-diacetylpyridine (2.4 g, 14.7 mmol) in absolute methanol (50 ml) was added 2,4,6-trimethylaniline (6.2 ml, 44.1 mmol). After the addition of several drops of formic acid, the reaction mixture was refluxed for 24 h and then allowed to cool down to room temperature. The crude product precipitated as yellow powder. Pure 2,6-bis[1-(2,4,6-trimethylphenylimino)ethyl]pyridine was obtained in 83% yield (4.8 g). A mixture of this ligand (0.30 g, 0.75 mmol) and CdCl2.2.5H2O (0.17 g, 0.75 mmol) in acetonitrile was stirred at room temperature for 12 h. Evaporation of the solvent gave the crude product as a yellowish powder. Yellowish needle crystals suitable for X-ray diffraction were obtained upon recrystallization from acetonitrile/dichloromethane (2:1 v/v) (yield 84%, 0.39 g).
H atoms were positioned geometrically and refined as riding, with C—H = 0.93Å (CH) and Uiso(H) = 1.2Ueq(C), and with C—H = 0.96Å (CH3) and Uiso(H) = 1.5Ueq(C).
Luminescent coordination compounds based on pyridine-type ligands have attracted intensive attention due to their potential applications in the areas of sensor technologies and electro-luminescent devices (Tang & Vanslyke, 1987; Wang, 2001). In order to explore potential luminescent complexes of this type, we have reported a series of cadmium complexes derived from bis(iminoalkyl)pyridine ligands (Fan et al., 2004). We report here the crystal structure of the title compound, a new cadmium complex with 2,6-bis[1-(2,4,6-trimethylphenylimino)ethyl]pyridine ligand.
As shown in Fig. 1, the asymmetric unit of the title compound contains one independent complex molecule and a solvated acetonitrile molecule. The central CdII atom is five-coordinated in a distorted trigonal-bipyramidal geometry, defined by two Cl atoms, one pyridine N and two imine N atoms from the bis(iminoalkyl)pyridine ligand. The Cd—N bond lengths [2.306 (3)–2.416 (3) Å] (Table 1) fall into the range of observed values in the similar cadmium complexes (Fan et al., 2004). The dihedral angles between the substituted phenyl rings and the plane formed by three coordinated N atoms are 90.6 (1)° and 86.0 (1)°, respectively.
In the crystal structure, weak intermolecular C—H···Cl hydrogen bonds (Table 2) play an important role to link the molecules into a three-dimensional supramolecular network (Fig.2).
For related literature, see: Fan et al. (2004); Tang & Vanslyke (1987); Wang (2001).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
[Cd(C27H31N3)Cl2]·C2H3N | F(000) = 1272 |
Mr = 621.90 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6108 reflections |
a = 14.545 (3) Å | θ = 1.7–26.1° |
b = 15.074 (3) Å | µ = 0.93 mm−1 |
c = 14.758 (3) Å | T = 295 K |
β = 111.516 (2)° | Needle, yellow |
V = 3010.3 (11) Å3 | 0.42 × 0.20 × 0.18 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 5948 independent reflections |
Radiation source: fine-focus sealed tube | 4046 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
φ and ω scans | θmax = 26.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.697, Tmax = 0.851 | k = −16→18 |
16698 measured reflections | l = −18→15 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0303P)2] where P = (Fo2 + 2Fc2)/3 |
5948 reflections | (Δ/σ)max = 0.009 |
334 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
[Cd(C27H31N3)Cl2]·C2H3N | V = 3010.3 (11) Å3 |
Mr = 621.90 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.545 (3) Å | µ = 0.93 mm−1 |
b = 15.074 (3) Å | T = 295 K |
c = 14.758 (3) Å | 0.42 × 0.20 × 0.18 mm |
β = 111.516 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 5948 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4046 reflections with I > 2σ(I) |
Tmin = 0.697, Tmax = 0.851 | Rint = 0.086 |
16698 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 0.88 | Δρmax = 0.69 e Å−3 |
5948 reflections | Δρmin = −0.39 e Å−3 |
334 parameters |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.749428 (18) | 0.180077 (17) | 0.306446 (18) | 0.04833 (11) | |
Cl1 | 0.57035 (7) | 0.16398 (7) | 0.23566 (9) | 0.0755 (3) | |
Cl2 | 0.84039 (7) | 0.04834 (7) | 0.29937 (8) | 0.0713 (3) | |
N1 | 0.76671 (19) | 0.18576 (18) | 0.4751 (2) | 0.0456 (7) | |
N2 | 0.81540 (19) | 0.31434 (18) | 0.3745 (2) | 0.0466 (7) | |
N3 | 0.7892 (2) | 0.2711 (2) | 0.1911 (2) | 0.0529 (7) | |
N4 | 0.6107 (4) | 0.4175 (3) | 0.5283 (5) | 0.1161 (18) | |
C1 | 0.7983 (2) | 0.2586 (2) | 0.5210 (2) | 0.0468 (9) | |
C2 | 0.8220 (2) | 0.3328 (2) | 0.4650 (3) | 0.0475 (9) | |
C3 | 0.8523 (3) | 0.4155 (3) | 0.5056 (3) | 0.0644 (11) | |
H3 | 0.8580 | 0.4278 | 0.5692 | 0.077* | |
C4 | 0.8738 (3) | 0.4796 (3) | 0.4492 (3) | 0.0695 (12) | |
H4 | 0.8911 | 0.5366 | 0.4736 | 0.083* | |
C5 | 0.8697 (3) | 0.4589 (2) | 0.3582 (3) | 0.0645 (11) | |
H5 | 0.8878 | 0.5006 | 0.3214 | 0.077* | |
C6 | 0.8381 (2) | 0.3750 (2) | 0.3204 (3) | 0.0508 (9) | |
C7 | 0.8266 (3) | 0.3479 (3) | 0.2199 (3) | 0.0547 (10) | |
C8 | 0.8127 (3) | 0.2753 (3) | 0.6248 (3) | 0.0652 (11) | |
H8A | 0.7982 | 0.2221 | 0.6529 | 0.098* | |
H8B | 0.7692 | 0.3219 | 0.6284 | 0.098* | |
H8C | 0.8800 | 0.2924 | 0.6601 | 0.098* | |
C9 | 0.8587 (3) | 0.4115 (3) | 0.1586 (3) | 0.0799 (13) | |
H9A | 0.8544 | 0.3829 | 0.0991 | 0.120* | |
H9B | 0.9258 | 0.4294 | 0.1937 | 0.120* | |
H9C | 0.8166 | 0.4627 | 0.1440 | 0.120* | |
C10 | 0.7476 (2) | 0.1111 (2) | 0.5263 (2) | 0.0453 (8) | |
C11 | 0.8242 (3) | 0.0495 (3) | 0.5670 (3) | 0.0547 (10) | |
C12 | 0.8031 (3) | −0.0242 (3) | 0.6125 (3) | 0.0657 (11) | |
H12 | 0.8530 | −0.0655 | 0.6407 | 0.079* | |
C13 | 0.7121 (3) | −0.0390 (3) | 0.6178 (3) | 0.0653 (11) | |
C14 | 0.6400 (3) | 0.0233 (3) | 0.5782 (3) | 0.0611 (10) | |
H14 | 0.5783 | 0.0146 | 0.5824 | 0.073* | |
C15 | 0.6555 (3) | 0.0993 (2) | 0.5317 (3) | 0.0525 (9) | |
C16 | 0.9252 (3) | 0.0656 (3) | 0.5663 (3) | 0.0762 (13) | |
H16A | 0.9659 | 0.0146 | 0.5920 | 0.114* | |
H16B | 0.9537 | 0.1165 | 0.6057 | 0.114* | |
H16C | 0.9208 | 0.0761 | 0.5007 | 0.114* | |
C17 | 0.6943 (4) | −0.1210 (3) | 0.6687 (4) | 0.1025 (17) | |
H17A | 0.6443 | −0.1087 | 0.6949 | 0.154* | |
H17B | 0.7545 | −0.1374 | 0.7206 | 0.154* | |
H17C | 0.6730 | −0.1689 | 0.6228 | 0.154* | |
C18 | 0.5753 (3) | 0.1681 (3) | 0.4925 (3) | 0.0726 (12) | |
H18A | 0.5961 | 0.2225 | 0.5278 | 0.109* | |
H18B | 0.5160 | 0.1474 | 0.4998 | 0.109* | |
H18C | 0.5628 | 0.1781 | 0.4247 | 0.109* | |
C19 | 0.7759 (3) | 0.2367 (2) | 0.0965 (3) | 0.0545 (9) | |
C20 | 0.6847 (3) | 0.2440 (3) | 0.0224 (3) | 0.0680 (11) | |
C21 | 0.6716 (4) | 0.2024 (3) | −0.0655 (3) | 0.0825 (14) | |
H21 | 0.6104 | 0.2065 | −0.1160 | 0.099* | |
C22 | 0.7456 (5) | 0.1553 (3) | −0.0807 (4) | 0.0856 (15) | |
C23 | 0.8366 (4) | 0.1519 (3) | −0.0054 (4) | 0.0835 (14) | |
H23 | 0.8880 | 0.1216 | −0.0150 | 0.100* | |
C24 | 0.8540 (3) | 0.1918 (3) | 0.0835 (3) | 0.0681 (11) | |
C25 | 0.6026 (3) | 0.2975 (3) | 0.0350 (3) | 0.0898 (15) | |
H25A | 0.5823 | 0.2700 | 0.0833 | 0.135* | |
H25B | 0.5475 | 0.3000 | −0.0258 | 0.135* | |
H25C | 0.6256 | 0.3565 | 0.0555 | 0.135* | |
C26 | 0.7284 (5) | 0.1099 (4) | −0.1777 (4) | 0.132 (2) | |
H26A | 0.6675 | 0.0772 | −0.1976 | 0.198* | |
H26B | 0.7820 | 0.0701 | −0.1707 | 0.198* | |
H26C | 0.7247 | 0.1539 | −0.2260 | 0.198* | |
C27 | 0.9545 (3) | 0.1863 (3) | 0.1635 (4) | 0.0876 (15) | |
H27A | 0.9981 | 0.1525 | 0.1412 | 0.131* | |
H27B | 0.9488 | 0.1578 | 0.2194 | 0.131* | |
H27C | 0.9807 | 0.2449 | 0.1808 | 0.131* | |
C28 | 0.5801 (5) | 0.4177 (4) | 0.4466 (6) | 0.098 (2) | |
C29 | 0.5408 (5) | 0.4164 (5) | 0.3409 (5) | 0.156 (3) | |
H29A | 0.5294 | 0.3561 | 0.3185 | 0.234* | |
H29B | 0.5874 | 0.4434 | 0.3172 | 0.234* | |
H29C | 0.4797 | 0.4487 | 0.3171 | 0.234* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.05459 (18) | 0.04431 (16) | 0.04645 (17) | 0.00312 (13) | 0.01896 (13) | −0.00318 (12) |
Cl1 | 0.0547 (6) | 0.0804 (8) | 0.0827 (8) | 0.0069 (5) | 0.0148 (5) | −0.0143 (6) |
Cl2 | 0.0732 (7) | 0.0640 (7) | 0.0751 (8) | 0.0229 (5) | 0.0252 (6) | −0.0017 (5) |
N1 | 0.0445 (16) | 0.0469 (17) | 0.0471 (18) | 0.0001 (14) | 0.0189 (14) | −0.0005 (14) |
N2 | 0.0485 (17) | 0.0431 (16) | 0.0477 (19) | −0.0003 (14) | 0.0169 (14) | −0.0012 (14) |
N3 | 0.0654 (19) | 0.053 (2) | 0.0445 (19) | 0.0105 (16) | 0.0254 (15) | 0.0009 (14) |
N4 | 0.109 (4) | 0.097 (4) | 0.147 (5) | −0.001 (3) | 0.052 (4) | 0.015 (4) |
C1 | 0.043 (2) | 0.059 (2) | 0.038 (2) | 0.0008 (17) | 0.0146 (16) | −0.0017 (17) |
C2 | 0.046 (2) | 0.050 (2) | 0.044 (2) | −0.0054 (16) | 0.0139 (17) | −0.0056 (17) |
C3 | 0.078 (3) | 0.061 (3) | 0.054 (3) | −0.013 (2) | 0.025 (2) | −0.014 (2) |
C4 | 0.087 (3) | 0.050 (2) | 0.067 (3) | −0.016 (2) | 0.023 (2) | −0.011 (2) |
C5 | 0.079 (3) | 0.046 (2) | 0.070 (3) | −0.007 (2) | 0.028 (2) | 0.006 (2) |
C6 | 0.055 (2) | 0.048 (2) | 0.052 (2) | 0.0065 (18) | 0.0226 (19) | 0.0077 (18) |
C7 | 0.059 (2) | 0.052 (2) | 0.057 (3) | 0.0104 (19) | 0.026 (2) | 0.0110 (18) |
C8 | 0.071 (3) | 0.078 (3) | 0.048 (2) | −0.013 (2) | 0.023 (2) | −0.008 (2) |
C9 | 0.120 (4) | 0.062 (3) | 0.073 (3) | −0.008 (3) | 0.053 (3) | 0.010 (2) |
C10 | 0.050 (2) | 0.049 (2) | 0.038 (2) | −0.0051 (17) | 0.0179 (17) | −0.0026 (15) |
C11 | 0.061 (2) | 0.063 (3) | 0.041 (2) | 0.005 (2) | 0.0196 (19) | 0.0036 (18) |
C12 | 0.085 (3) | 0.062 (3) | 0.046 (3) | 0.014 (2) | 0.019 (2) | 0.0099 (19) |
C13 | 0.086 (3) | 0.065 (3) | 0.048 (3) | −0.011 (2) | 0.028 (2) | 0.002 (2) |
C14 | 0.072 (3) | 0.067 (3) | 0.054 (3) | −0.017 (2) | 0.034 (2) | −0.008 (2) |
C15 | 0.056 (2) | 0.052 (2) | 0.054 (2) | −0.0070 (19) | 0.0249 (19) | −0.0075 (18) |
C16 | 0.063 (3) | 0.098 (4) | 0.067 (3) | 0.018 (2) | 0.024 (2) | 0.019 (2) |
C17 | 0.134 (4) | 0.084 (4) | 0.095 (4) | −0.012 (3) | 0.049 (3) | 0.033 (3) |
C18 | 0.060 (3) | 0.073 (3) | 0.094 (4) | 0.001 (2) | 0.040 (2) | −0.003 (2) |
C19 | 0.072 (3) | 0.056 (2) | 0.043 (2) | 0.011 (2) | 0.031 (2) | 0.0057 (18) |
C20 | 0.087 (3) | 0.064 (3) | 0.054 (3) | 0.013 (2) | 0.027 (2) | 0.006 (2) |
C21 | 0.109 (4) | 0.082 (3) | 0.046 (3) | 0.004 (3) | 0.016 (3) | 0.008 (2) |
C22 | 0.139 (5) | 0.069 (3) | 0.061 (3) | 0.011 (3) | 0.051 (3) | −0.003 (2) |
C23 | 0.123 (4) | 0.072 (3) | 0.079 (4) | 0.026 (3) | 0.065 (3) | 0.008 (3) |
C24 | 0.094 (3) | 0.061 (3) | 0.062 (3) | 0.016 (2) | 0.044 (3) | 0.011 (2) |
C25 | 0.094 (3) | 0.106 (4) | 0.065 (3) | 0.036 (3) | 0.024 (3) | 0.011 (3) |
C26 | 0.222 (7) | 0.123 (5) | 0.065 (4) | 0.012 (4) | 0.069 (4) | −0.024 (3) |
C27 | 0.077 (3) | 0.102 (4) | 0.096 (4) | 0.025 (3) | 0.047 (3) | 0.019 (3) |
C28 | 0.093 (4) | 0.072 (3) | 0.144 (6) | 0.005 (3) | 0.060 (5) | 0.023 (4) |
C29 | 0.188 (7) | 0.158 (7) | 0.131 (7) | −0.002 (5) | 0.069 (5) | 0.037 (5) |
Cd1—N2 | 2.306 (3) | C14—C15 | 1.396 (5) |
Cd1—N1 | 2.410 (3) | C14—H14 | 0.9300 |
Cd1—Cl2 | 2.4097 (10) | C15—C18 | 1.507 (5) |
Cd1—N3 | 2.416 (3) | C16—H16A | 0.9600 |
Cd1—Cl1 | 2.4369 (11) | C16—H16B | 0.9600 |
N1—C1 | 1.284 (4) | C16—H16C | 0.9600 |
N1—C10 | 1.438 (4) | C17—H17A | 0.9600 |
N2—C6 | 1.332 (4) | C17—H17B | 0.9600 |
N2—C2 | 1.332 (4) | C17—H17C | 0.9600 |
N3—C7 | 1.284 (4) | C18—H18A | 0.9600 |
N3—C19 | 1.434 (4) | C18—H18B | 0.9600 |
N4—C28 | 1.123 (7) | C18—H18C | 0.9600 |
C1—C8 | 1.490 (5) | C19—C20 | 1.380 (5) |
C1—C2 | 1.504 (5) | C19—C24 | 1.395 (5) |
C2—C3 | 1.385 (5) | C20—C21 | 1.390 (6) |
C3—C4 | 1.383 (5) | C20—C25 | 1.507 (5) |
C3—H3 | 0.9300 | C21—C22 | 1.374 (6) |
C4—C5 | 1.358 (5) | C21—H21 | 0.9300 |
C4—H4 | 0.9300 | C22—C23 | 1.383 (6) |
C5—C6 | 1.391 (5) | C22—C26 | 1.523 (6) |
C5—H5 | 0.9300 | C23—C24 | 1.380 (6) |
C6—C7 | 1.488 (5) | C23—H23 | 0.9300 |
C7—C9 | 1.505 (5) | C24—C27 | 1.507 (6) |
C8—H8A | 0.9600 | C25—H25A | 0.9600 |
C8—H8B | 0.9600 | C25—H25B | 0.9600 |
C8—H8C | 0.9600 | C25—H25C | 0.9600 |
C9—H9A | 0.9600 | C26—H26A | 0.9600 |
C9—H9B | 0.9600 | C26—H26B | 0.9600 |
C9—H9C | 0.9600 | C26—H26C | 0.9600 |
C10—C15 | 1.382 (4) | C27—H27A | 0.9600 |
C10—C11 | 1.405 (5) | C27—H27B | 0.9600 |
C11—C12 | 1.389 (5) | C27—H27C | 0.9600 |
C11—C16 | 1.493 (5) | C28—C29 | 1.451 (8) |
C12—C13 | 1.373 (5) | C29—H29A | 0.9600 |
C12—H12 | 0.9300 | C29—H29B | 0.9600 |
C13—C14 | 1.369 (5) | C29—H29C | 0.9600 |
C13—C17 | 1.517 (5) | ||
N2—Cd1—N1 | 69.50 (10) | C15—C14—H14 | 118.8 |
N2—Cd1—Cl2 | 126.50 (7) | C10—C15—C14 | 117.9 (4) |
N1—Cd1—Cl2 | 102.89 (7) | C10—C15—C18 | 121.2 (3) |
N2—Cd1—N3 | 68.88 (10) | C14—C15—C18 | 120.8 (3) |
N1—Cd1—N3 | 138.28 (10) | C11—C16—H16A | 109.5 |
Cl2—Cd1—N3 | 99.21 (7) | C11—C16—H16B | 109.5 |
N2—Cd1—Cl1 | 118.86 (7) | H16A—C16—H16B | 109.5 |
N1—Cd1—Cl1 | 97.85 (7) | C11—C16—H16C | 109.5 |
Cl2—Cd1—Cl1 | 114.64 (4) | H16A—C16—H16C | 109.5 |
N3—Cd1—Cl1 | 104.43 (7) | H16B—C16—H16C | 109.5 |
C1—N1—C10 | 119.5 (3) | C13—C17—H17A | 109.5 |
C1—N1—Cd1 | 117.2 (2) | C13—C17—H17B | 109.5 |
C10—N1—Cd1 | 123.2 (2) | H17A—C17—H17B | 109.5 |
C6—N2—C2 | 121.0 (3) | C13—C17—H17C | 109.5 |
C6—N2—Cd1 | 119.8 (2) | H17A—C17—H17C | 109.5 |
C2—N2—Cd1 | 119.0 (2) | H17B—C17—H17C | 109.5 |
C7—N3—C19 | 122.6 (3) | C15—C18—H18A | 109.5 |
C7—N3—Cd1 | 117.4 (2) | C15—C18—H18B | 109.5 |
C19—N3—Cd1 | 120.0 (2) | H18A—C18—H18B | 109.5 |
N1—C1—C8 | 125.1 (3) | C15—C18—H18C | 109.5 |
N1—C1—C2 | 117.1 (3) | H18A—C18—H18C | 109.5 |
C8—C1—C2 | 117.8 (3) | H18B—C18—H18C | 109.5 |
N2—C2—C3 | 121.1 (3) | C20—C19—C24 | 121.7 (4) |
N2—C2—C1 | 116.7 (3) | C20—C19—N3 | 119.3 (3) |
C3—C2—C1 | 122.1 (3) | C24—C19—N3 | 118.9 (3) |
C4—C3—C2 | 118.3 (4) | C19—C20—C21 | 117.8 (4) |
C4—C3—H3 | 120.8 | C19—C20—C25 | 121.3 (4) |
C2—C3—H3 | 120.8 | C21—C20—C25 | 120.9 (4) |
C5—C4—C3 | 119.8 (4) | C22—C21—C20 | 122.5 (4) |
C5—C4—H4 | 120.1 | C22—C21—H21 | 118.7 |
C3—C4—H4 | 120.1 | C20—C21—H21 | 118.7 |
C4—C5—C6 | 119.5 (4) | C21—C22—C23 | 117.7 (4) |
C4—C5—H5 | 120.2 | C21—C22—C26 | 121.1 (5) |
C6—C5—H5 | 120.2 | C23—C22—C26 | 121.2 (5) |
N2—C6—C5 | 120.1 (4) | C24—C23—C22 | 122.3 (4) |
N2—C6—C7 | 116.6 (3) | C24—C23—H23 | 118.8 |
C5—C6—C7 | 123.3 (3) | C22—C23—H23 | 118.8 |
N3—C7—C6 | 117.2 (3) | C23—C24—C19 | 117.9 (4) |
N3—C7—C9 | 124.2 (4) | C23—C24—C27 | 120.5 (4) |
C6—C7—C9 | 118.6 (4) | C19—C24—C27 | 121.6 (4) |
C1—C8—H8A | 109.5 | C20—C25—H25A | 109.5 |
C1—C8—H8B | 109.5 | C20—C25—H25B | 109.5 |
H8A—C8—H8B | 109.5 | H25A—C25—H25B | 109.5 |
C1—C8—H8C | 109.5 | C20—C25—H25C | 109.5 |
H8A—C8—H8C | 109.5 | H25A—C25—H25C | 109.5 |
H8B—C8—H8C | 109.5 | H25B—C25—H25C | 109.5 |
C7—C9—H9A | 109.5 | C22—C26—H26A | 109.5 |
C7—C9—H9B | 109.5 | C22—C26—H26B | 109.5 |
H9A—C9—H9B | 109.5 | H26A—C26—H26B | 109.5 |
C7—C9—H9C | 109.5 | C22—C26—H26C | 109.5 |
H9A—C9—H9C | 109.5 | H26A—C26—H26C | 109.5 |
H9B—C9—H9C | 109.5 | H26B—C26—H26C | 109.5 |
C15—C10—C11 | 121.6 (3) | C24—C27—H27A | 109.5 |
C15—C10—N1 | 120.6 (3) | C24—C27—H27B | 109.5 |
C11—C10—N1 | 117.8 (3) | H27A—C27—H27B | 109.5 |
C12—C11—C10 | 117.1 (3) | C24—C27—H27C | 109.5 |
C12—C11—C16 | 121.7 (4) | H27A—C27—H27C | 109.5 |
C10—C11—C16 | 121.2 (3) | H27B—C27—H27C | 109.5 |
C13—C12—C11 | 123.0 (4) | N4—C28—C29 | 179.0 (7) |
C13—C12—H12 | 118.5 | C28—C29—H29A | 109.5 |
C11—C12—H12 | 118.5 | C28—C29—H29B | 109.5 |
C14—C13—C12 | 117.9 (4) | H29A—C29—H29B | 109.5 |
C14—C13—C17 | 121.9 (4) | C28—C29—H29C | 109.5 |
C12—C13—C17 | 120.2 (4) | H29A—C29—H29C | 109.5 |
C13—C14—C15 | 122.5 (4) | H29B—C29—H29C | 109.5 |
C13—C14—H14 | 118.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8C···Cl1i | 0.96 | 2.66 | 3.614 (4) | 172 |
C16—H16A···Cl2ii | 0.96 | 2.84 | 3.681 (4) | 146 |
C16—H16C···Cl2 | 0.96 | 2.80 | 3.680 (4) | 153 |
C29—H29B···Cl2iii | 0.96 | 2.81 | 3.721 (6) | 159 |
C5—H5···Cl1iii | 0.93 | 2.74 | 3.622 (4) | 158 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+2, −y, −z+1; (iii) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C27H31N3)Cl2]·C2H3N |
Mr | 621.90 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 14.545 (3), 15.074 (3), 14.758 (3) |
β (°) | 111.516 (2) |
V (Å3) | 3010.3 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.93 |
Crystal size (mm) | 0.42 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.697, 0.851 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16698, 5948, 4046 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.091, 0.88 |
No. of reflections | 5948 |
No. of parameters | 334 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −0.39 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
Cd1—N2 | 2.306 (3) | Cd1—N3 | 2.416 (3) |
Cd1—N1 | 2.410 (3) | Cd1—Cl1 | 2.4369 (11) |
Cd1—Cl2 | 2.4097 (10) | ||
N2—Cd1—N1 | 69.50 (10) | Cl2—Cd1—N3 | 99.21 (7) |
N2—Cd1—Cl2 | 126.50 (7) | N2—Cd1—Cl1 | 118.86 (7) |
N1—Cd1—Cl2 | 102.89 (7) | N1—Cd1—Cl1 | 97.85 (7) |
N2—Cd1—N3 | 68.88 (10) | Cl2—Cd1—Cl1 | 114.64 (4) |
N1—Cd1—N3 | 138.28 (10) | N3—Cd1—Cl1 | 104.43 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8C···Cl1i | 0.96 | 2.66 | 3.614 (4) | 172 |
C16—H16A···Cl2ii | 0.96 | 2.84 | 3.681 (4) | 146 |
C16—H16C···Cl2 | 0.96 | 2.80 | 3.680 (4) | 153 |
C29—H29B···Cl2iii | 0.96 | 2.81 | 3.721 (6) | 159 |
C5—H5···Cl1iii | 0.93 | 2.74 | 3.622 (4) | 158 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+2, −y, −z+1; (iii) −x+3/2, y+1/2, −z+1/2. |
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Luminescent coordination compounds based on pyridine-type ligands have attracted intensive attention due to their potential applications in the areas of sensor technologies and electro-luminescent devices (Tang & Vanslyke, 1987; Wang, 2001). In order to explore potential luminescent complexes of this type, we have reported a series of cadmium complexes derived from bis(iminoalkyl)pyridine ligands (Fan et al., 2004). We report here the crystal structure of the title compound, a new cadmium complex with 2,6-bis[1-(2,4,6-trimethylphenylimino)ethyl]pyridine ligand.
As shown in Fig. 1, the asymmetric unit of the title compound contains one independent complex molecule and a solvated acetonitrile molecule. The central CdII atom is five-coordinated in a distorted trigonal-bipyramidal geometry, defined by two Cl atoms, one pyridine N and two imine N atoms from the bis(iminoalkyl)pyridine ligand. The Cd—N bond lengths [2.306 (3)–2.416 (3) Å] (Table 1) fall into the range of observed values in the similar cadmium complexes (Fan et al., 2004). The dihedral angles between the substituted phenyl rings and the plane formed by three coordinated N atoms are 90.6 (1)° and 86.0 (1)°, respectively.
In the crystal structure, weak intermolecular C—H···Cl hydrogen bonds (Table 2) play an important role to link the molecules into a three-dimensional supramolecular network (Fig.2).