Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038524/zl2054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038524/zl2054Isup2.hkl |
CCDC reference: 660071
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.019
- wR factor = 0.051
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1 (2) 2.02
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For related literature, see: Fornies-Marquina et al. (1974); Molina et al. (1989); Naveen et al. (2006).
For related literature, see: Huang et al. (2005).
The title complex was prepared by the addition of a stoichiometric amount of cadmium chloride (1 mmol) to a hot methanol solution (10 ml) of 2-methyl-5-phenyl-s-triazolo(3,4 - b)-1,3,4-thiadiazole (1 mmol). The resulting solution was filtered, and yellow blocky crystals were obtained on slow evaporation of the solvent over several days at room temperature.
Carbon-bound and hydroxyl H atoms were placed at calculated positions and were treated as riding on the parent C atoms with C—H = 0.93–0.97 or O—H = 0.82 Å, and with Uiso(H) = 1.2 or 1.5 Ueq(C, O). The terminal methyl and hydroxyl groups were also allowed free rotation.
The molecular structure of 6-methyl-3-phenyl-[1,2,4]triazolo(3,4 - b)-1,3,4-thiadiazole (Fornies-Marquina et al., 1974) and its substituted derivatives (Molina et al., 1989; Huang et al., 2005; Naveen et al., 2006) have been reported, however, no metal complexes of these ligands have so far been reported. In this paper, we report the crystal structure of the title compound, (I), a Cd complex obtained by the reaction of 6-methyl-3-phenyl-[1,2,4]triazolo(3,4 - b)-1,3,4-thiadiazole with cadmium chloride in methanol solution.
As illustrated in Fig. 1, the CdII atom, which is a neutral mononuclear molecule, lies on a centre of symmetry and has a distorted octahedral geometry with six coordinating atoms: two N atoms from two 6-methyl-3-phenyl-[1,2,4]triazolo(3,4 - b)-1,3,4-thiadiazole, two O from two methanol molecules and two chlorine atoms (Table 1). The structural components are connected through O—H···Cl hydrogen bonding involving the coordinating methanol molecules as donors and the Cl atoms as acceptors and π-π stacking interactions between the phenyl and triazolo rings, thus forming a supramolecular network structure (Fig. 2; Table 2). The centroid-centroid distance of adjacent phenyl and triazolo rings (at 1 - x,-y,1 - z) is 3.613 (7) Å, indicating a normal π-π interaction.
For related literature, see: Fornies-Marquina et al. (1974); Molina et al. (1989); Naveen et al. (2006).
For related literature, see: Huang et al. (2005).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.
[CdCl2(C10H8N4S)2(CH4O)2] | Z = 1 |
Mr = 679.91 | F(000) = 342 |
Triclinic, P1 | Dx = 1.714 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7576 (9) Å | Cell parameters from 2400 reflections |
b = 8.6138 (11) Å | θ = 1.4–28.0° |
c = 12.1019 (15) Å | µ = 1.23 mm−1 |
α = 95.588 (1)° | T = 291 K |
β = 104.037 (1)° | Block, yellow |
γ = 102.496 (1)° | 0.44 × 0.31 × 0.22 mm |
V = 658.81 (15) Å3 |
Bruker APEX II area-detector diffractometer | 2386 independent reflections |
Radiation source: fine-focus sealed tube | 2327 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
φ and ω scans | θmax = 25.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.633, Tmax = 0.764 | k = −10→10 |
4509 measured reflections | l = −14→14 |
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)] = 0.019 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.051 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0249P)2 + 0.3405P] where P = (Fo2 + 2Fc2)/3 |
2386 reflections | (Δ/σ)max < 0.001 |
171 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
[CdCl2(C10H8N4S)2(CH4O)2] | γ = 102.496 (1)° |
Mr = 679.91 | V = 658.81 (15) Å3 |
Triclinic, P1 | Z = 1 |
a = 6.7576 (9) Å | Mo Kα radiation |
b = 8.6138 (11) Å | µ = 1.23 mm−1 |
c = 12.1019 (15) Å | T = 291 K |
α = 95.588 (1)° | 0.44 × 0.31 × 0.22 mm |
β = 104.037 (1)° |
Bruker APEX II area-detector diffractometer | 2386 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2327 reflections with I > 2σ(I) |
Tmin = 0.633, Tmax = 0.764 | Rint = 0.011 |
4509 measured reflections |
R[F2 > 2σ(F2)] = 0.019 | 0 restraints |
wR(F2) = 0.051 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.46 e Å−3 |
2386 reflections | Δρmin = −0.45 e Å−3 |
171 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 | ||
Cd1 | 0.0000 | 1.0000 | 0.0000 | 0.02382 (7) | |
Cl1 | 0.21045 (8) | 0.79569 (6) | −0.04065 (4) | 0.03678 (13) | |
S1 | −0.03252 (8) | 0.61793 (6) | 0.16761 (4) | 0.03174 (12) | |
O1 | 0.3105 (2) | 1.20734 (17) | 0.02416 (13) | 0.0378 (3) | |
H1A | 0.3961 | 1.1971 | −0.0245 | 0.057* | |
N1 | 0.0945 (3) | 0.9611 (2) | 0.19295 (13) | 0.0293 (4) | |
N2 | 0.1805 (3) | 1.0753 (2) | 0.29327 (14) | 0.0287 (3) | |
C7 | 0.1962 (3) | 0.9992 (2) | 0.38328 (16) | 0.0257 (4) | |
N3 | 0.1205 (2) | 0.83616 (18) | 0.34395 (13) | 0.0249 (3) | |
N4 | 0.0906 (3) | 0.69736 (19) | 0.39330 (14) | 0.0280 (3) | |
C1 | 0.3662 (3) | 1.2428 (3) | 0.52946 (18) | 0.0343 (4) | |
H1 | 0.3696 | 1.3028 | 0.4698 | 0.041* | |
C2 | 0.4460 (4) | 1.3187 (3) | 0.6438 (2) | 0.0411 (5) | |
H2 | 0.5006 | 1.4298 | 0.6600 | 0.049* | |
C3 | 0.4446 (3) | 1.2307 (3) | 0.73328 (18) | 0.0410 (5) | |
H3 | 0.4988 | 1.2822 | 0.8093 | 0.049* | |
C4 | 0.3625 (4) | 1.0656 (3) | 0.70944 (18) | 0.0400 (5) | |
H4 | 0.3622 | 1.0061 | 0.7696 | 0.048* | |
C5 | 0.2802 (3) | 0.9882 (3) | 0.59548 (17) | 0.0336 (4) | |
H5 | 0.2244 | 0.8773 | 0.5797 | 0.040* | |
C6 | 0.2815 (3) | 1.0772 (2) | 0.50492 (16) | 0.0266 (4) | |
C10 | 0.0617 (3) | 0.8198 (2) | 0.22672 (15) | 0.0265 (4) | |
C8 | 0.0103 (3) | 0.5756 (2) | 0.31026 (16) | 0.0292 (4) | |
C9 | −0.0456 (4) | 0.4066 (3) | 0.33259 (19) | 0.0425 (5) | |
H9A | 0.0025 | 0.4046 | 0.4138 | 0.064* | |
H9B | 0.0203 | 0.3415 | 0.2915 | 0.064* | |
H9C | −0.1957 | 0.3649 | 0.3069 | 0.064* | |
C11 | 0.3701 (4) | 1.3467 (3) | 0.1099 (2) | 0.0519 (6) | |
H10A | 0.2510 | 1.3914 | 0.1077 | 0.078* | |
H10B | 0.4814 | 1.4250 | 0.0953 | 0.078* | |
H10C | 0.4179 | 1.3176 | 0.1846 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.02905 (11) | 0.02292 (11) | 0.01872 (10) | 0.00580 (8) | 0.00528 (7) | 0.00425 (7) |
Cl1 | 0.0386 (3) | 0.0388 (3) | 0.0361 (3) | 0.0168 (2) | 0.0112 (2) | 0.0022 (2) |
S1 | 0.0461 (3) | 0.0253 (2) | 0.0220 (2) | 0.0082 (2) | 0.0065 (2) | 0.00352 (19) |
O1 | 0.0324 (8) | 0.0315 (8) | 0.0454 (9) | 0.0019 (6) | 0.0123 (7) | −0.0034 (6) |
N1 | 0.0398 (9) | 0.0263 (8) | 0.0215 (8) | 0.0093 (7) | 0.0066 (7) | 0.0040 (6) |
N2 | 0.0361 (9) | 0.0262 (8) | 0.0229 (8) | 0.0077 (7) | 0.0067 (7) | 0.0024 (6) |
C7 | 0.0270 (9) | 0.0270 (9) | 0.0240 (9) | 0.0083 (8) | 0.0077 (7) | 0.0036 (7) |
N3 | 0.0309 (8) | 0.0254 (8) | 0.0193 (7) | 0.0085 (7) | 0.0066 (6) | 0.0058 (6) |
N4 | 0.0349 (9) | 0.0270 (8) | 0.0247 (8) | 0.0095 (7) | 0.0094 (7) | 0.0091 (7) |
C1 | 0.0363 (11) | 0.0329 (11) | 0.0320 (10) | 0.0079 (9) | 0.0070 (9) | 0.0042 (9) |
C2 | 0.0391 (12) | 0.0353 (11) | 0.0410 (12) | 0.0058 (9) | 0.0046 (9) | −0.0075 (10) |
C3 | 0.0365 (11) | 0.0537 (14) | 0.0268 (10) | 0.0108 (10) | 0.0036 (9) | −0.0089 (10) |
C4 | 0.0432 (12) | 0.0532 (14) | 0.0242 (10) | 0.0129 (11) | 0.0091 (9) | 0.0072 (9) |
C5 | 0.0380 (11) | 0.0349 (11) | 0.0267 (10) | 0.0073 (9) | 0.0081 (8) | 0.0042 (8) |
C6 | 0.0240 (9) | 0.0323 (10) | 0.0230 (9) | 0.0089 (8) | 0.0055 (7) | 0.0006 (8) |
C10 | 0.0328 (10) | 0.0279 (10) | 0.0200 (9) | 0.0097 (8) | 0.0068 (7) | 0.0049 (7) |
C8 | 0.0353 (10) | 0.0297 (10) | 0.0247 (9) | 0.0105 (8) | 0.0082 (8) | 0.0084 (8) |
C9 | 0.0642 (15) | 0.0284 (11) | 0.0323 (11) | 0.0081 (10) | 0.0096 (10) | 0.0089 (9) |
C11 | 0.0438 (13) | 0.0419 (14) | 0.0585 (16) | 0.0012 (11) | 0.0091 (11) | −0.0136 (11) |
Cd1—N1i | 2.3438 (16) | C1—C6 | 1.390 (3) |
Cd1—N1 | 2.3438 (16) | C1—C2 | 1.394 (3) |
Cd1—O1i | 2.3785 (14) | C1—H1 | 0.9300 |
Cd1—O1 | 2.3785 (14) | C2—C3 | 1.382 (3) |
Cd1—Cl1 | 2.5721 (5) | C2—H2 | 0.9300 |
Cd1—Cl1i | 2.5721 (5) | C3—C4 | 1.383 (3) |
S1—C10 | 1.731 (2) | C3—H3 | 0.9300 |
S1—C8 | 1.7672 (19) | C4—C5 | 1.394 (3) |
O1—C11 | 1.423 (3) | C4—H4 | 0.9300 |
O1—H1A | 0.9300 | C5—C6 | 1.398 (3) |
N1—C10 | 1.313 (3) | C5—H5 | 0.9300 |
N1—N2 | 1.399 (2) | C8—C9 | 1.491 (3) |
N2—C7 | 1.319 (3) | C9—H9A | 0.9600 |
C7—N3 | 1.379 (2) | C9—H9B | 0.9600 |
C7—C6 | 1.476 (2) | C9—H9C | 0.9600 |
N3—C10 | 1.362 (2) | C11—H10A | 0.9600 |
N3—N4 | 1.386 (2) | C11—H10B | 0.9600 |
N4—C8 | 1.299 (3) | C11—H10C | 0.9600 |
N1i—Cd1—N1 | 180.00 (8) | C3—C2—C1 | 120.7 (2) |
N1i—Cd1—O1i | 93.09 (6) | C3—C2—H2 | 119.7 |
N1—Cd1—O1i | 86.91 (6) | C1—C2—H2 | 119.7 |
N1i—Cd1—O1 | 86.91 (6) | C2—C3—C4 | 119.8 (2) |
N1—Cd1—O1 | 93.09 (6) | C2—C3—H3 | 120.1 |
O1i—Cd1—O1 | 180.0 | C4—C3—H3 | 120.1 |
N1i—Cd1—Cl1 | 93.32 (4) | C3—C4—C5 | 120.1 (2) |
N1—Cd1—Cl1 | 86.68 (4) | C3—C4—H4 | 119.9 |
O1i—Cd1—Cl1 | 92.17 (4) | C5—C4—H4 | 119.9 |
O1—Cd1—Cl1 | 87.83 (4) | C4—C5—C6 | 120.1 (2) |
N1i—Cd1—Cl1i | 86.68 (4) | C4—C5—H5 | 120.0 |
N1—Cd1—Cl1i | 93.32 (4) | C6—C5—H5 | 120.0 |
O1i—Cd1—Cl1i | 87.83 (4) | C1—C6—C5 | 119.51 (18) |
O1—Cd1—Cl1i | 92.17 (4) | C1—C6—C7 | 118.98 (18) |
Cl1—Cd1—Cl1i | 180.00 (2) | C5—C6—C7 | 121.51 (18) |
C10—S1—C8 | 87.32 (9) | N1—C10—N3 | 110.67 (16) |
C11—O1—Cd1 | 122.51 (14) | N1—C10—S1 | 139.33 (15) |
C11—O1—H1A | 118.8 | N3—C10—S1 | 110.00 (14) |
Cd1—O1—H1A | 118.7 | N4—C8—C9 | 122.19 (18) |
C10—N1—N2 | 106.37 (15) | N4—C8—S1 | 117.17 (15) |
C10—N1—Cd1 | 124.10 (12) | C9—C8—S1 | 120.63 (15) |
N2—N1—Cd1 | 129.41 (12) | C8—C9—H9A | 109.5 |
C7—N2—N1 | 108.57 (15) | C8—C9—H9B | 109.5 |
N2—C7—N3 | 108.37 (16) | H9A—C9—H9B | 109.5 |
N2—C7—C6 | 125.23 (17) | C8—C9—H9C | 109.5 |
N3—C7—C6 | 126.40 (17) | H9A—C9—H9C | 109.5 |
C10—N3—C7 | 106.01 (15) | H9B—C9—H9C | 109.5 |
C10—N3—N4 | 117.68 (15) | O1—C11—H10A | 109.5 |
C7—N3—N4 | 136.30 (15) | O1—C11—H10B | 109.5 |
C8—N4—N3 | 107.80 (15) | H10A—C11—H10B | 109.5 |
C6—C1—C2 | 119.8 (2) | O1—C11—H10C | 109.5 |
C6—C1—H1 | 120.1 | H10A—C11—H10C | 109.5 |
C2—C1—H1 | 120.1 | H10B—C11—H10C | 109.5 |
Symmetry code: (i) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···Cl1ii | 0.93 | 2.57 | 3.2005 (16) | 126 |
Symmetry code: (ii) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | [CdCl2(C10H8N4S)2(CH4O)2] |
Mr | 679.91 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 6.7576 (9), 8.6138 (11), 12.1019 (15) |
α, β, γ (°) | 95.588 (1), 104.037 (1), 102.496 (1) |
V (Å3) | 658.81 (15) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.23 |
Crystal size (mm) | 0.44 × 0.31 × 0.22 |
Data collection | |
Diffractometer | Bruker APEX II area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.633, 0.764 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4509, 2386, 2327 |
Rint | 0.011 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.019, 0.051, 1.12 |
No. of reflections | 2386 |
No. of parameters | 171 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.45 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTL.
Cd1—N1 | 2.3438 (16) | Cd1—Cl1 | 2.5721 (5) |
Cd1—O1 | 2.3785 (14) | ||
N1i—Cd1—O1i | 93.09 (6) | N1—Cd1—Cl1 | 86.68 (4) |
N1i—Cd1—O1 | 86.91 (6) | O1i—Cd1—Cl1 | 92.17 (4) |
N1—Cd1—O1 | 93.09 (6) | O1—Cd1—Cl1 | 87.83 (4) |
N1i—Cd1—Cl1 | 93.32 (4) |
Symmetry code: (i) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···Cl1ii | 0.93 | 2.57 | 3.2005 (16) | 125.6 |
Symmetry code: (ii) −x+1, −y+2, −z. |
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The molecular structure of 6-methyl-3-phenyl-[1,2,4]triazolo(3,4 - b)-1,3,4-thiadiazole (Fornies-Marquina et al., 1974) and its substituted derivatives (Molina et al., 1989; Huang et al., 2005; Naveen et al., 2006) have been reported, however, no metal complexes of these ligands have so far been reported. In this paper, we report the crystal structure of the title compound, (I), a Cd complex obtained by the reaction of 6-methyl-3-phenyl-[1,2,4]triazolo(3,4 - b)-1,3,4-thiadiazole with cadmium chloride in methanol solution.
As illustrated in Fig. 1, the CdII atom, which is a neutral mononuclear molecule, lies on a centre of symmetry and has a distorted octahedral geometry with six coordinating atoms: two N atoms from two 6-methyl-3-phenyl-[1,2,4]triazolo(3,4 - b)-1,3,4-thiadiazole, two O from two methanol molecules and two chlorine atoms (Table 1). The structural components are connected through O—H···Cl hydrogen bonding involving the coordinating methanol molecules as donors and the Cl atoms as acceptors and π-π stacking interactions between the phenyl and triazolo rings, thus forming a supramolecular network structure (Fig. 2; Table 2). The centroid-centroid distance of adjacent phenyl and triazolo rings (at 1 - x,-y,1 - z) is 3.613 (7) Å, indicating a normal π-π interaction.