The reaction of 2-cyanopyridine with N-phenylthiosemicarbazide afforded 2-[amino(pyridin-2-yl)methylidene]-N-phenylhydrazine-1-carbothioamide (Ham4ph) and crystals of 4-phenyl-5-(pyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (pyph3NS, 1, C13H10N4S). Crystals of methyl 2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate (phpy2NS, 2, C16H14N4O2S), derived from 1, were obtained by the reaction of Ham4ph with chloroacetic acid, followed by the acid-catalyzed esterification of the carboxylic acid with methyl alcohol. Crystals of bis(methanol-κO)bis(methyl 2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl-κ2N1,N5]sulfanyl}acetato)zinc(II)/cadmium(II) hexabromidocadmate(II), [Zn0.76Cd0.24(C16H14N4O2S)2(CH3OH)2][Cd2Br6] or [Zn0.76Cd0.24(phpy2NS)2(MeOH)2][Cd2Br6], 3, and dichlorido(methyl 2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl-κ2N1,N5]sulfanyl}acetato)mercury(II), [HgCl2(C16H14N4O2S)] or [Hg(phpy2NS)Cl2], 4, were synthesized using ligand 2 and CdBr2 or HgCl2, respectively. The molecular and supramolecular structures of the compounds were studied by X-ray diffractometry. The asymmetric unit of 3 is formed from CdBr3 and M(phpy2NS)(MeOH) units, where the metal centre M has a 76% occupancy of ZnII and 24% of CdII. The M2+ centre of the cation, located on a crystallographic inversion centre, is hexacoordinated and appears as a slightly distorted octahedral [MN4O2]2+ cation. The Cd centre of the anion is coordinated by two terminal bromide ligands and two bridging bromide ligands that generate [Cd2Br6]2− cadmium–bromide clusters. These clusters display crystallographic inversion symmetry forming two edge-shared tetrahedra and serve as agents that direct the structure in the formation of supramolecular assemblies. In mononuclear complex 4, the coordination geometry around the Hg2+ ion is distorted tetrahedral and comprises two chloride ligands and two N-atom donors from the phpy2NS ligand, viz. one pyridine N atom and the other from triazole. In the crystal packing, all four compounds exhibit weak intermolecular interactions, which facilitate the formation of three-dimensional architectures. Along with the noncovalent interactions, the structural diversity in the complexes can be attributed to the metal centre and to the coordination geometry, as well as to its ionic or neutral character.
Supporting information
CCDC references: 1837084; 1915706; 1837083; 1849847
Data collection: APEX2 (Bruker, 2014) for Compound_1; APEX2 (Bruker, 2005) for Compound_2, Compound_4; APEX3 (Bruker, 2017) for Compound_3. Cell refinement: APEX2 (Bruker, 2014) for Compound_1; APEX2 (Bruker, 2005) for Compound_2, Compound_4; SAINT (Bruker, 2017) for Compound_3. Data reduction: APEX2 (Bruker, 2014) for Compound_1; APEX2 (Bruker, 2005) for Compound_2, Compound_4; SAINT (Bruker, 2017) for Compound_3. Program(s) used to solve structure: SHELXS2013 (Sheldrick, 2015a) for Compound_1, Compound_2, Compound_4; SHELXT2014 (Sheldrick, 2015a) for Compound_3. Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015b) for Compound_1, Compound_2, Compound_4; SHELXL2017 (Sheldrick, 2015b) for Compound_3. Molecular graphics: PLATON (Spek, 2009) and DIAMOND (Brandenburg, 2018) for Compound_1; PLATON (Spek, 2009) for Compound_2, Compound_3, Compound_4. Software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015b) for Compound_1, Compound_2, Compound_4; SHELXL2017 (Sheldrick, 2015b) for Compound_3.
4-Phenyl-5-(pyridin-2-yl)-2,4-dihydro-3
H-1,2,4-triazole-3-thione (Compound_1)
top
Crystal data top
C13H10N4S | F(000) = 1056 |
Mr = 254.31 | Dx = 1.424 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 28.6467 (6) Å | Cell parameters from 7950 reflections |
b = 5.6358 (1) Å | θ = 2.8–26.3° |
c = 15.1374 (3) Å | µ = 0.26 mm−1 |
β = 103.896 (1)° | T = 100 K |
V = 2372.36 (8) Å3 | Needle, colourless |
Z = 8 | 0.32 × 0.09 × 0.02 mm |
Data collection top
Bruker X8 KappaAPEXII CCD diffractometer | 3615 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
ω and phi scans | θmax = 26.4°, θmin = 0.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −35→34 |
Tmin = 0.856, Tmax = 1.000 | k = 0→7 |
56310 measured reflections | l = 0→18 |
4845 independent reflections | |
Refinement top
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: mixed |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0424P)2 + 1.0135P] where P = (Fo2 + 2Fc2)/3 |
4845 reflections | (Δ/σ)max < 0.001 |
325 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1A | 0.07921 (2) | −0.01168 (9) | 0.57505 (3) | 0.01689 (13) | |
N1A | 0.13609 (6) | 0.6282 (3) | 0.33029 (11) | 0.0164 (4) | |
N2A | 0.02707 (6) | 0.4525 (3) | 0.38576 (11) | 0.0177 (4) | |
N3A | 0.02438 (6) | 0.2753 (3) | 0.44604 (11) | 0.0170 (4) | |
H30A | −0.0039 | 0.2099 | 0.4486 | 0.020* | |
N4A | 0.09957 (6) | 0.3411 (3) | 0.46401 (10) | 0.0124 (4) | |
C1A | 0.15198 (7) | 0.7877 (4) | 0.27900 (13) | 0.0177 (5) | |
H1A | 0.1826 | 0.7618 | 0.2670 | 0.021* | |
C2A | 0.12668 (7) | 0.9884 (4) | 0.24216 (13) | 0.0184 (5) | |
H2A | 0.1403 | 1.0990 | 0.2081 | 0.022* | |
C3A | 0.08122 (7) | 1.0241 (4) | 0.25609 (13) | 0.0187 (5) | |
H3A | 0.0626 | 1.1580 | 0.2306 | 0.022* | |
C4A | 0.06339 (7) | 0.8613 (4) | 0.30772 (13) | 0.0170 (5) | |
H4A | 0.0322 | 0.8802 | 0.3183 | 0.020* | |
C5A | 0.09214 (7) | 0.6683 (4) | 0.34399 (13) | 0.0139 (4) | |
C6A | 0.07315 (7) | 0.4912 (3) | 0.39818 (13) | 0.0140 (4) | |
C7A | 0.06721 (7) | 0.2012 (4) | 0.49485 (13) | 0.0151 (4) | |
C8A | 0.15081 (7) | 0.3316 (4) | 0.50179 (13) | 0.0130 (4) | |
C9A | 0.17355 (7) | 0.5192 (4) | 0.55312 (13) | 0.0158 (4) | |
H9A | 0.1562 | 0.6585 | 0.5605 | 0.019* | |
C10A | 0.22226 (7) | 0.5004 (4) | 0.59368 (14) | 0.0192 (5) | |
H10A | 0.2385 | 0.6285 | 0.6289 | 0.023* | |
C11A | 0.24742 (7) | 0.2961 (4) | 0.58329 (14) | 0.0201 (5) | |
H11A | 0.2806 | 0.2829 | 0.6124 | 0.024* | |
C12A | 0.22409 (7) | 0.1119 (4) | 0.53051 (14) | 0.0185 (5) | |
H12A | 0.2415 | −0.0267 | 0.5223 | 0.022* | |
C13A | 0.17530 (7) | 0.1285 (4) | 0.48933 (13) | 0.0159 (4) | |
H13A | 0.1591 | 0.0019 | 0.4532 | 0.019* | |
S1B | 0.42065 (2) | −0.00196 (9) | 0.50621 (3) | 0.01597 (13) | |
N1B | 0.36653 (6) | 0.6337 (3) | 0.20866 (11) | 0.0169 (4) | |
N2B | 0.47426 (6) | 0.4576 (3) | 0.36486 (11) | 0.0175 (4) | |
N3B | 0.47616 (6) | 0.2806 (3) | 0.42748 (11) | 0.0166 (4) | |
H30B | 0.5019 | 0.2175 | 0.4533 | 0.020* | |
N4B | 0.40137 (5) | 0.3542 (3) | 0.37752 (10) | 0.0122 (4) | |
C1B | 0.35119 (7) | 0.7911 (4) | 0.14176 (14) | 0.0195 (5) | |
H1B | 0.3209 | 0.7635 | 0.1008 | 0.023* | |
C2B | 0.37665 (7) | 0.9919 (4) | 0.12830 (14) | 0.0191 (5) | |
H2B | 0.3637 | 1.1000 | 0.0806 | 0.023* | |
C3B | 0.42113 (7) | 1.0311 (4) | 0.18564 (14) | 0.0186 (5) | |
H3B | 0.4396 | 1.1661 | 0.1778 | 0.022* | |
C4B | 0.43849 (7) | 0.8710 (4) | 0.25469 (14) | 0.0171 (5) | |
H4B | 0.4692 | 0.8923 | 0.2949 | 0.021* | |
C5B | 0.40976 (7) | 0.6770 (4) | 0.26404 (13) | 0.0147 (4) | |
C6B | 0.42849 (7) | 0.5007 (4) | 0.33553 (13) | 0.0144 (4) | |
C7B | 0.43295 (7) | 0.2108 (4) | 0.43694 (13) | 0.0141 (4) | |
C8B | 0.34996 (7) | 0.3560 (4) | 0.36700 (12) | 0.0127 (4) | |
C9B | 0.32857 (7) | 0.5518 (4) | 0.39552 (13) | 0.0159 (4) | |
H9B | 0.3475 | 0.6839 | 0.4218 | 0.019* | |
C10B | 0.27916 (7) | 0.5530 (4) | 0.38522 (14) | 0.0193 (5) | |
H10B | 0.2641 | 0.6869 | 0.4045 | 0.023* | |
C11B | 0.25182 (7) | 0.3608 (4) | 0.34710 (14) | 0.0203 (5) | |
H11B | 0.2179 | 0.3625 | 0.3398 | 0.024* | |
C12B | 0.27401 (7) | 0.1655 (4) | 0.31954 (14) | 0.0195 (5) | |
H12B | 0.2552 | 0.0324 | 0.2939 | 0.023* | |
C13B | 0.32316 (7) | 0.1619 (4) | 0.32883 (13) | 0.0159 (4) | |
H13B | 0.3383 | 0.0283 | 0.3093 | 0.019* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1A | 0.0139 (3) | 0.0164 (3) | 0.0205 (3) | −0.0008 (2) | 0.0046 (2) | 0.0050 (2) |
N1A | 0.0150 (9) | 0.0170 (10) | 0.0161 (9) | −0.0010 (7) | 0.0017 (7) | 0.0000 (7) |
N2A | 0.0146 (9) | 0.0151 (10) | 0.0232 (9) | −0.0012 (7) | 0.0038 (7) | 0.0049 (8) |
N3A | 0.0105 (9) | 0.0161 (9) | 0.0250 (9) | −0.0021 (7) | 0.0055 (7) | 0.0046 (8) |
N4A | 0.0104 (8) | 0.0109 (9) | 0.0160 (8) | −0.0007 (7) | 0.0034 (7) | 0.0021 (7) |
C1A | 0.0146 (10) | 0.0201 (12) | 0.0193 (10) | −0.0037 (9) | 0.0058 (9) | −0.0012 (9) |
C2A | 0.0230 (11) | 0.0170 (11) | 0.0150 (10) | −0.0043 (10) | 0.0041 (9) | 0.0015 (9) |
C3A | 0.0227 (11) | 0.0136 (11) | 0.0175 (10) | −0.0008 (9) | 0.0000 (9) | 0.0007 (9) |
C4A | 0.0163 (11) | 0.0157 (11) | 0.0175 (10) | 0.0006 (9) | 0.0011 (9) | −0.0018 (9) |
C5A | 0.0140 (10) | 0.0140 (11) | 0.0128 (10) | −0.0033 (9) | 0.0014 (8) | −0.0029 (8) |
C6A | 0.0124 (10) | 0.0122 (11) | 0.0170 (10) | 0.0012 (9) | 0.0024 (8) | −0.0012 (9) |
C7A | 0.0130 (10) | 0.0140 (11) | 0.0191 (10) | −0.0022 (9) | 0.0053 (9) | −0.0017 (9) |
C8A | 0.0117 (10) | 0.0164 (11) | 0.0115 (9) | 0.0002 (8) | 0.0038 (8) | 0.0030 (8) |
C9A | 0.0183 (11) | 0.0135 (11) | 0.0159 (10) | 0.0003 (9) | 0.0046 (8) | 0.0008 (9) |
C10A | 0.0183 (11) | 0.0206 (12) | 0.0169 (10) | −0.0078 (10) | 0.0004 (8) | −0.0009 (9) |
C11A | 0.0123 (10) | 0.0273 (13) | 0.0202 (11) | −0.0016 (10) | 0.0031 (9) | 0.0042 (10) |
C12A | 0.0161 (11) | 0.0181 (12) | 0.0221 (11) | 0.0035 (9) | 0.0064 (9) | 0.0042 (10) |
C13A | 0.0177 (11) | 0.0145 (11) | 0.0161 (10) | −0.0028 (9) | 0.0055 (9) | 0.0002 (9) |
S1B | 0.0147 (3) | 0.0145 (3) | 0.0184 (3) | −0.0006 (2) | 0.0034 (2) | 0.0040 (2) |
N1B | 0.0156 (9) | 0.0186 (10) | 0.0174 (9) | 0.0022 (8) | 0.0061 (7) | 0.0002 (8) |
N2B | 0.0145 (9) | 0.0161 (10) | 0.0218 (9) | 0.0016 (7) | 0.0040 (7) | 0.0063 (8) |
N3B | 0.0109 (9) | 0.0155 (9) | 0.0223 (9) | 0.0021 (7) | 0.0017 (7) | 0.0074 (8) |
N4B | 0.0108 (8) | 0.0105 (9) | 0.0150 (8) | 0.0009 (7) | 0.0025 (7) | 0.0024 (7) |
C1B | 0.0152 (11) | 0.0252 (12) | 0.0177 (10) | 0.0045 (9) | 0.0033 (9) | 0.0011 (10) |
C2B | 0.0211 (11) | 0.0200 (12) | 0.0172 (10) | 0.0062 (10) | 0.0068 (9) | 0.0041 (9) |
C3B | 0.0223 (11) | 0.0136 (11) | 0.0234 (11) | 0.0014 (9) | 0.0122 (9) | 0.0015 (9) |
C4B | 0.0135 (10) | 0.0171 (12) | 0.0216 (11) | 0.0012 (9) | 0.0059 (9) | −0.0003 (9) |
C5B | 0.0135 (10) | 0.0148 (11) | 0.0176 (10) | 0.0033 (8) | 0.0077 (9) | 0.0011 (9) |
C6B | 0.0149 (10) | 0.0125 (11) | 0.0166 (10) | −0.0010 (9) | 0.0052 (8) | −0.0002 (9) |
C7B | 0.0123 (10) | 0.0127 (11) | 0.0161 (10) | 0.0010 (8) | 0.0012 (8) | −0.0015 (9) |
C8B | 0.0116 (10) | 0.0157 (11) | 0.0112 (9) | 0.0010 (8) | 0.0033 (8) | 0.0032 (8) |
C9B | 0.0183 (11) | 0.0137 (11) | 0.0158 (10) | −0.0002 (9) | 0.0039 (9) | −0.0007 (9) |
C10B | 0.0183 (11) | 0.0194 (12) | 0.0218 (11) | 0.0061 (9) | 0.0082 (9) | 0.0035 (9) |
C11B | 0.0120 (10) | 0.0267 (13) | 0.0225 (11) | 0.0011 (9) | 0.0050 (9) | 0.0080 (10) |
C12B | 0.0173 (11) | 0.0199 (12) | 0.0203 (11) | −0.0054 (9) | 0.0023 (9) | 0.0025 (9) |
C13B | 0.0200 (11) | 0.0127 (11) | 0.0153 (10) | −0.0006 (9) | 0.0047 (9) | −0.0006 (9) |
Geometric parameters (Å, º) top
S1A—C7A | 1.683 (2) | S1B—C7B | 1.685 (2) |
N1A—C1A | 1.337 (3) | N1B—C1B | 1.339 (3) |
N1A—C5A | 1.343 (2) | N1B—C5B | 1.341 (3) |
N2A—C6A | 1.306 (2) | N2B—C6B | 1.302 (2) |
N2A—N3A | 1.367 (2) | N2B—N3B | 1.368 (2) |
N3A—C7A | 1.338 (3) | N3B—C7B | 1.339 (2) |
N3A—H30A | 0.9002 | N3B—H30B | 0.8276 |
N4A—C7A | 1.381 (2) | N4B—C7B | 1.375 (3) |
N4A—C6A | 1.385 (3) | N4B—C6B | 1.388 (2) |
N4A—C8A | 1.443 (2) | N4B—C8B | 1.443 (2) |
C1A—C2A | 1.386 (3) | C1B—C2B | 1.388 (3) |
C1A—H1A | 0.9500 | C1B—H1B | 0.9500 |
C2A—C3A | 1.383 (3) | C2B—C3B | 1.376 (3) |
C2A—H2A | 0.9500 | C2B—H2B | 0.9500 |
C3A—C4A | 1.381 (3) | C3B—C4B | 1.380 (3) |
C3A—H3A | 0.9500 | C3B—H3B | 0.9500 |
C4A—C5A | 1.395 (3) | C4B—C5B | 1.396 (3) |
C4A—H4A | 0.9500 | C4B—H4B | 0.9500 |
C5A—C6A | 1.476 (3) | C5B—C6B | 1.472 (3) |
C8A—C13A | 1.379 (3) | C8B—C9B | 1.381 (3) |
C8A—C9A | 1.379 (3) | C8B—C13B | 1.381 (3) |
C9A—C10A | 1.387 (3) | C9B—C10B | 1.386 (3) |
C9A—H9A | 0.9500 | C9B—H9B | 0.9500 |
C10A—C11A | 1.387 (3) | C10B—C11B | 1.379 (3) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.380 (3) | C11B—C12B | 1.385 (3) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—C13A | 1.390 (3) | C12B—C13B | 1.381 (3) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
| | | |
C1A—N1A—C5A | 116.03 (18) | C1B—N1B—C5B | 116.01 (18) |
C6A—N2A—N3A | 104.05 (16) | C6B—N2B—N3B | 103.98 (15) |
C7A—N3A—N2A | 113.92 (15) | C7B—N3B—N2B | 113.86 (16) |
C7A—N3A—H30A | 124.4 | C7B—N3B—H30B | 124.4 |
N2A—N3A—H30A | 121.6 | N2B—N3B—H30B | 121.5 |
C7A—N4A—C6A | 107.24 (16) | C7B—N4B—C6B | 107.25 (15) |
C7A—N4A—C8A | 123.14 (16) | C7B—N4B—C8B | 124.76 (15) |
C6A—N4A—C8A | 129.49 (16) | C6B—N4B—C8B | 127.89 (16) |
N1A—C1A—C2A | 124.35 (18) | N1B—C1B—C2B | 124.2 (2) |
N1A—C1A—H1A | 117.8 | N1B—C1B—H1B | 117.9 |
C2A—C1A—H1A | 117.8 | C2B—C1B—H1B | 117.9 |
C3A—C2A—C1A | 118.55 (19) | C3B—C2B—C1B | 118.5 (2) |
C3A—C2A—H2A | 120.7 | C3B—C2B—H2B | 120.7 |
C1A—C2A—H2A | 120.7 | C1B—C2B—H2B | 120.7 |
C4A—C3A—C2A | 118.6 (2) | C2B—C3B—C4B | 118.92 (19) |
C4A—C3A—H3A | 120.7 | C2B—C3B—H3B | 120.5 |
C2A—C3A—H3A | 120.7 | C4B—C3B—H3B | 120.5 |
C3A—C4A—C5A | 118.52 (19) | C3B—C4B—C5B | 118.3 (2) |
C3A—C4A—H4A | 120.7 | C3B—C4B—H4B | 120.8 |
C5A—C4A—H4A | 120.7 | C5B—C4B—H4B | 120.8 |
N1A—C5A—C4A | 123.85 (18) | N1B—C5B—C4B | 123.90 (19) |
N1A—C5A—C6A | 117.15 (18) | N1B—C5B—C6B | 117.11 (17) |
C4A—C5A—C6A | 118.96 (17) | C4B—C5B—C6B | 118.90 (19) |
N2A—C6A—N4A | 111.12 (17) | N2B—C6B—N4B | 111.19 (17) |
N2A—C6A—C5A | 121.84 (18) | N2B—C6B—C5B | 122.41 (17) |
N4A—C6A—C5A | 126.99 (17) | N4B—C6B—C5B | 126.35 (17) |
N3A—C7A—N4A | 103.67 (17) | N3B—C7B—N4B | 103.72 (16) |
N3A—C7A—S1A | 128.49 (15) | N3B—C7B—S1B | 127.78 (16) |
N4A—C7A—S1A | 127.85 (15) | N4B—C7B—S1B | 128.50 (15) |
C13A—C8A—C9A | 121.78 (18) | C9B—C8B—C13B | 121.32 (18) |
C13A—C8A—N4A | 118.62 (18) | C9B—C8B—N4B | 119.27 (18) |
C9A—C8A—N4A | 119.52 (17) | C13B—C8B—N4B | 119.40 (17) |
C8A—C9A—C10A | 118.65 (19) | C8B—C9B—C10B | 119.12 (19) |
C8A—C9A—H9A | 120.7 | C8B—C9B—H9B | 120.4 |
C10A—C9A—H9A | 120.7 | C10B—C9B—H9B | 120.4 |
C9A—C10A—C11A | 120.5 (2) | C11B—C10B—C9B | 120.3 (2) |
C9A—C10A—H10A | 119.7 | C11B—C10B—H10B | 119.8 |
C11A—C10A—H10A | 119.7 | C9B—C10B—H10B | 119.8 |
C12A—C11A—C10A | 119.8 (2) | C10B—C11B—C12B | 119.66 (19) |
C12A—C11A—H11A | 120.1 | C10B—C11B—H11B | 120.2 |
C10A—C11A—H11A | 120.1 | C12B—C11B—H11B | 120.2 |
C11A—C12A—C13A | 120.3 (2) | C13B—C12B—C11B | 120.8 (2) |
C11A—C12A—H12A | 119.9 | C13B—C12B—H12B | 119.6 |
C13A—C12A—H12A | 119.9 | C11B—C12B—H12B | 119.6 |
C8A—C13A—C12A | 118.95 (19) | C12B—C13B—C8B | 118.81 (19) |
C8A—C13A—H13A | 120.5 | C12B—C13B—H13B | 120.6 |
C12A—C13A—H13A | 120.5 | C8B—C13B—H13B | 120.6 |
| | | |
C6A—N2A—N3A—C7A | −0.6 (2) | C6B—N2B—N3B—C7B | 0.8 (2) |
C5A—N1A—C1A—C2A | 1.4 (3) | C5B—N1B—C1B—C2B | −1.0 (3) |
N1A—C1A—C2A—C3A | −2.4 (3) | N1B—C1B—C2B—C3B | 1.6 (3) |
C1A—C2A—C3A—C4A | 1.4 (3) | C1B—C2B—C3B—C4B | −0.6 (3) |
C2A—C3A—C4A—C5A | 0.3 (3) | C2B—C3B—C4B—C5B | −0.8 (3) |
C1A—N1A—C5A—C4A | 0.5 (3) | C1B—N1B—C5B—C4B | −0.5 (3) |
C1A—N1A—C5A—C6A | 178.28 (17) | C1B—N1B—C5B—C6B | −177.19 (17) |
C3A—C4A—C5A—N1A | −1.3 (3) | C3B—C4B—C5B—N1B | 1.4 (3) |
C3A—C4A—C5A—C6A | −179.11 (18) | C3B—C4B—C5B—C6B | 178.03 (17) |
N3A—N2A—C6A—N4A | 0.7 (2) | N3B—N2B—C6B—N4B | −0.5 (2) |
N3A—N2A—C6A—C5A | 178.44 (17) | N3B—N2B—C6B—C5B | −178.03 (17) |
C7A—N4A—C6A—N2A | −0.6 (2) | C7B—N4B—C6B—N2B | 0.0 (2) |
C8A—N4A—C6A—N2A | −176.51 (17) | C8B—N4B—C6B—N2B | 176.47 (17) |
C7A—N4A—C6A—C5A | −178.18 (18) | C7B—N4B—C6B—C5B | 177.44 (18) |
C8A—N4A—C6A—C5A | 5.9 (3) | C8B—N4B—C6B—C5B | −6.1 (3) |
N1A—C5A—C6A—N2A | −151.01 (19) | N1B—C5B—C6B—N2B | 148.14 (19) |
C4A—C5A—C6A—N2A | 26.9 (3) | C4B—C5B—C6B—N2B | −28.7 (3) |
N1A—C5A—C6A—N4A | 26.4 (3) | N1B—C5B—C6B—N4B | −29.1 (3) |
C4A—C5A—C6A—N4A | −155.68 (19) | C4B—C5B—C6B—N4B | 154.11 (19) |
N2A—N3A—C7A—N4A | 0.2 (2) | N2B—N3B—C7B—N4B | −0.8 (2) |
N2A—N3A—C7A—S1A | −179.79 (15) | N2B—N3B—C7B—S1B | 179.55 (15) |
C6A—N4A—C7A—N3A | 0.2 (2) | C6B—N4B—C7B—N3B | 0.5 (2) |
C8A—N4A—C7A—N3A | 176.44 (16) | C8B—N4B—C7B—N3B | −176.13 (17) |
C6A—N4A—C7A—S1A | −179.78 (15) | C6B—N4B—C7B—S1B | −179.89 (15) |
C8A—N4A—C7A—S1A | −3.5 (3) | C8B—N4B—C7B—S1B | 3.5 (3) |
C7A—N4A—C8A—C13A | 67.2 (2) | C7B—N4B—C8B—C9B | 111.1 (2) |
C6A—N4A—C8A—C13A | −117.4 (2) | C6B—N4B—C8B—C9B | −64.8 (3) |
C7A—N4A—C8A—C9A | −109.4 (2) | C7B—N4B—C8B—C13B | −68.8 (2) |
C6A—N4A—C8A—C9A | 66.0 (3) | C6B—N4B—C8B—C13B | 115.3 (2) |
C13A—C8A—C9A—C10A | −0.6 (3) | C13B—C8B—C9B—C10B | −0.2 (3) |
N4A—C8A—C9A—C10A | 175.94 (16) | N4B—C8B—C9B—C10B | 179.92 (17) |
C8A—C9A—C10A—C11A | −0.5 (3) | C8B—C9B—C10B—C11B | 0.1 (3) |
C9A—C10A—C11A—C12A | 1.5 (3) | C9B—C10B—C11B—C12B | 0.4 (3) |
C10A—C11A—C12A—C13A | −1.4 (3) | C10B—C11B—C12B—C13B | −0.7 (3) |
C9A—C8A—C13A—C12A | 0.7 (3) | C11B—C12B—C13B—C8B | 0.6 (3) |
N4A—C8A—C13A—C12A | −175.85 (16) | C9B—C8B—C13B—C12B | −0.2 (3) |
C11A—C12A—C13A—C8A | 0.3 (3) | N4B—C8B—C13B—C12B | 179.71 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H30A···S1Ai | 0.90 | 2.38 | 3.2652 (17) | 168 |
N3B—H30B···S1Bii | 0.83 | 2.47 | 3.2844 (17) | 167 |
C9A—H9A···S1Aiii | 0.95 | 2.93 | 3.851 (2) | 163 |
C9B—H9B···S1Biii | 0.95 | 2.81 | 3.737 (2) | 167 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x, y+1, z. |
Methyl
2-{[4-phenyl-5-(pyridin-2-yl)-4
H-1,2,4-triazol-3-yl]sulfanyl}acetate (Compound_2)
top
Crystal data top
C16H14N4O2S | F(000) = 680 |
Mr = 326.37 | Dx = 1.434 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5945 (4) Å | Cell parameters from 1985 reflections |
b = 18.9451 (12) Å | θ = 2.6–27.5° |
c = 14.2664 (9) Å | µ = 0.23 mm−1 |
β = 90.247 (2)° | T = 100 K |
V = 1512.06 (17) Å3 | Needle, colourless |
Z = 4 | 0.37 × 0.12 × 0.07 mm |
Data collection top
Bruker X8 KappaAPEXII CCD diffractometer | 2547 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
ω and phi scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −7→7 |
Tmin = 0.877, Tmax = 1.000 | k = 0→24 |
12949 measured reflections | l = 0→18 |
3477 independent reflections | |
Refinement top
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)] = 0.043 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.9896P] where P = (Fo2 + 2Fc2)/3 |
3477 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.20698 (9) | 0.12113 (2) | 0.21106 (4) | 0.01795 (14) | |
O1 | −0.1803 (3) | −0.01805 (8) | 0.07974 (11) | 0.0322 (4) | |
O2 | −0.1751 (3) | 0.09974 (8) | 0.09434 (11) | 0.0258 (4) | |
N11 | 0.8544 (3) | 0.20684 (8) | 0.48756 (11) | 0.0160 (4) | |
N12 | 0.6813 (3) | 0.04296 (8) | 0.38104 (12) | 0.0182 (4) | |
N13 | 0.4967 (3) | 0.03447 (8) | 0.31590 (12) | 0.0185 (4) | |
N14 | 0.5649 (3) | 0.14888 (8) | 0.33479 (11) | 0.0131 (3) | |
C1 | 0.0898 (4) | 0.03338 (10) | 0.18950 (15) | 0.0202 (4) | |
H1A | 0.2212 | 0.0020 | 0.1691 | 0.024* | |
H1B | 0.0233 | 0.0141 | 0.2483 | 0.024* | |
C2 | −0.1027 (4) | 0.03469 (10) | 0.11514 (14) | 0.0191 (4) | |
C3 | −0.3438 (4) | 0.10677 (12) | 0.01610 (16) | 0.0288 (5) | |
H3A | −0.2664 | 0.0918 | −0.0421 | 0.043* | |
H3B | −0.3939 | 0.1562 | 0.0104 | 0.043* | |
H3C | −0.4841 | 0.0771 | 0.0277 | 0.043* | |
C11 | 1.0152 (4) | 0.23352 (11) | 0.54808 (13) | 0.0182 (4) | |
H11 | 0.9920 | 0.2804 | 0.5699 | 0.022* | |
C12 | 1.2129 (4) | 0.19671 (11) | 0.58049 (14) | 0.0196 (4) | |
H12 | 1.3224 | 0.2182 | 0.6229 | 0.024* | |
C13 | 1.2481 (4) | 0.12818 (10) | 0.55007 (14) | 0.0189 (4) | |
H13 | 1.3805 | 0.1014 | 0.5721 | 0.023* | |
C14 | 1.0866 (4) | 0.09943 (10) | 0.48697 (14) | 0.0167 (4) | |
H14 | 1.1064 | 0.0526 | 0.4643 | 0.020* | |
C15 | 0.8940 (3) | 0.14082 (10) | 0.45739 (13) | 0.0137 (4) | |
C16 | 0.7189 (3) | 0.11093 (10) | 0.39126 (13) | 0.0140 (4) | |
C17 | 0.4314 (3) | 0.09820 (10) | 0.29054 (13) | 0.0152 (4) | |
C18 | 0.5461 (3) | 0.22383 (9) | 0.31734 (13) | 0.0134 (4) | |
C19 | 0.3445 (4) | 0.25903 (10) | 0.34786 (13) | 0.0161 (4) | |
H19 | 0.2231 | 0.2344 | 0.3808 | 0.019* | |
C110 | 0.3215 (4) | 0.33052 (10) | 0.32990 (14) | 0.0186 (4) | |
H110 | 0.1845 | 0.3553 | 0.3513 | 0.022* | |
C111 | 0.4979 (4) | 0.36617 (10) | 0.28068 (14) | 0.0179 (4) | |
H111 | 0.4815 | 0.4152 | 0.2681 | 0.021* | |
C112 | 0.6979 (4) | 0.32995 (10) | 0.25002 (14) | 0.0183 (4) | |
H112 | 0.8185 | 0.3544 | 0.2163 | 0.022* | |
C113 | 0.7242 (3) | 0.25809 (10) | 0.26813 (13) | 0.0164 (4) | |
H113 | 0.8613 | 0.2332 | 0.2471 | 0.020* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0195 (3) | 0.0117 (2) | 0.0226 (3) | 0.00077 (19) | −0.0084 (2) | −0.00143 (19) |
O1 | 0.0421 (10) | 0.0189 (8) | 0.0356 (9) | −0.0080 (7) | −0.0182 (8) | −0.0002 (7) |
O2 | 0.0267 (9) | 0.0184 (8) | 0.0321 (9) | 0.0005 (6) | −0.0154 (7) | −0.0024 (6) |
N11 | 0.0182 (9) | 0.0146 (8) | 0.0152 (8) | −0.0005 (6) | −0.0010 (7) | 0.0002 (6) |
N12 | 0.0200 (9) | 0.0136 (8) | 0.0210 (9) | 0.0007 (7) | −0.0058 (7) | 0.0002 (7) |
N13 | 0.0206 (9) | 0.0128 (8) | 0.0220 (9) | 0.0006 (7) | −0.0082 (7) | −0.0002 (7) |
N14 | 0.0138 (8) | 0.0103 (8) | 0.0152 (8) | 0.0003 (6) | −0.0020 (6) | −0.0008 (6) |
C1 | 0.0241 (11) | 0.0115 (9) | 0.0249 (11) | −0.0016 (8) | −0.0076 (9) | −0.0025 (8) |
C2 | 0.0206 (11) | 0.0162 (10) | 0.0205 (10) | −0.0037 (8) | −0.0020 (8) | 0.0020 (8) |
C3 | 0.0280 (13) | 0.0308 (13) | 0.0275 (12) | 0.0004 (10) | −0.0139 (10) | 0.0002 (9) |
C11 | 0.0224 (11) | 0.0173 (10) | 0.0150 (9) | −0.0010 (8) | −0.0009 (8) | −0.0022 (8) |
C12 | 0.0202 (11) | 0.0228 (11) | 0.0157 (10) | −0.0039 (8) | −0.0050 (8) | 0.0008 (8) |
C13 | 0.0172 (10) | 0.0211 (10) | 0.0184 (10) | 0.0002 (8) | −0.0030 (8) | 0.0049 (8) |
C14 | 0.0182 (10) | 0.0127 (9) | 0.0190 (10) | −0.0008 (8) | 0.0009 (8) | 0.0026 (7) |
C15 | 0.0140 (10) | 0.0140 (9) | 0.0132 (9) | −0.0015 (7) | 0.0009 (7) | 0.0029 (7) |
C16 | 0.0141 (10) | 0.0134 (9) | 0.0145 (9) | 0.0021 (7) | 0.0007 (8) | 0.0018 (7) |
C17 | 0.0140 (10) | 0.0132 (9) | 0.0183 (10) | 0.0001 (7) | −0.0012 (8) | −0.0023 (7) |
C18 | 0.0164 (10) | 0.0108 (9) | 0.0130 (9) | 0.0011 (7) | −0.0049 (8) | −0.0017 (7) |
C19 | 0.0168 (10) | 0.0136 (9) | 0.0178 (10) | −0.0021 (8) | −0.0007 (8) | −0.0018 (7) |
C110 | 0.0166 (10) | 0.0156 (10) | 0.0235 (11) | 0.0039 (8) | −0.0025 (8) | −0.0044 (8) |
C111 | 0.0230 (11) | 0.0099 (9) | 0.0207 (10) | −0.0006 (7) | −0.0090 (8) | 0.0004 (7) |
C112 | 0.0191 (11) | 0.0153 (10) | 0.0206 (10) | −0.0045 (8) | −0.0031 (8) | 0.0043 (8) |
C113 | 0.0121 (10) | 0.0191 (10) | 0.0180 (10) | 0.0015 (8) | −0.0007 (8) | −0.0001 (8) |
Geometric parameters (Å, º) top
S1—C17 | 1.743 (2) | C11—H11 | 0.9500 |
S1—C1 | 1.8128 (19) | C12—C13 | 1.383 (3) |
O1—C2 | 1.200 (2) | C12—H12 | 0.9500 |
O2—C2 | 1.330 (2) | C13—C14 | 1.384 (3) |
O2—C3 | 1.465 (2) | C13—H13 | 0.9500 |
N11—C15 | 1.342 (2) | C14—C15 | 1.396 (3) |
N11—C11 | 1.343 (2) | C14—H14 | 0.9500 |
N12—C16 | 1.313 (2) | C15—C16 | 1.470 (3) |
N12—N13 | 1.395 (2) | C18—C19 | 1.382 (3) |
N13—C17 | 1.312 (2) | C18—C113 | 1.383 (3) |
N14—C17 | 1.369 (2) | C19—C110 | 1.384 (3) |
N14—C16 | 1.379 (2) | C19—H19 | 0.9500 |
N14—C18 | 1.445 (2) | C110—C111 | 1.389 (3) |
C1—C2 | 1.509 (3) | C110—H110 | 0.9500 |
C1—H1A | 0.9900 | C111—C112 | 1.385 (3) |
C1—H1B | 0.9900 | C111—H111 | 0.9500 |
C3—H3A | 0.9800 | C112—C113 | 1.393 (3) |
C3—H3B | 0.9800 | C112—H112 | 0.9500 |
C3—H3C | 0.9800 | C113—H113 | 0.9500 |
C11—C12 | 1.385 (3) | | |
| | | |
C17—S1—C1 | 98.08 (9) | C14—C13—H13 | 120.7 |
C2—O2—C3 | 116.66 (16) | C13—C14—C15 | 118.44 (18) |
C15—N11—C11 | 116.48 (17) | C13—C14—H14 | 120.8 |
C16—N12—N13 | 107.75 (15) | C15—C14—H14 | 120.8 |
C17—N13—N12 | 106.38 (15) | N11—C15—C14 | 123.71 (18) |
C17—N14—C16 | 104.01 (15) | N11—C15—C16 | 117.02 (16) |
C17—N14—C18 | 124.78 (15) | C14—C15—C16 | 119.25 (17) |
C16—N14—C18 | 131.10 (16) | N12—C16—N14 | 110.30 (16) |
C2—C1—S1 | 111.14 (13) | N12—C16—C15 | 123.72 (17) |
C2—C1—H1A | 109.4 | N14—C16—C15 | 125.93 (17) |
S1—C1—H1A | 109.4 | N13—C17—N14 | 111.55 (17) |
C2—C1—H1B | 109.4 | N13—C17—S1 | 127.44 (15) |
S1—C1—H1B | 109.4 | N14—C17—S1 | 121.01 (14) |
H1A—C1—H1B | 108.0 | C19—C18—C113 | 121.59 (17) |
O1—C2—O2 | 124.62 (19) | C19—C18—N14 | 118.59 (17) |
O1—C2—C1 | 122.56 (18) | C113—C18—N14 | 119.78 (17) |
O2—C2—C1 | 112.81 (16) | C18—C19—C110 | 119.29 (19) |
O2—C3—H3A | 109.5 | C18—C19—H19 | 120.4 |
O2—C3—H3B | 109.5 | C110—C19—H19 | 120.4 |
H3A—C3—H3B | 109.5 | C19—C110—C111 | 120.23 (19) |
O2—C3—H3C | 109.5 | C19—C110—H110 | 119.9 |
H3A—C3—H3C | 109.5 | C111—C110—H110 | 119.9 |
H3B—C3—H3C | 109.5 | C112—C111—C110 | 119.70 (18) |
N11—C11—C12 | 123.84 (19) | C112—C111—H111 | 120.1 |
N11—C11—H11 | 118.1 | C110—C111—H111 | 120.1 |
C12—C11—H11 | 118.1 | C111—C112—C113 | 120.68 (18) |
C13—C12—C11 | 118.84 (18) | C111—C112—H112 | 119.7 |
C13—C12—H12 | 120.6 | C113—C112—H112 | 119.7 |
C11—C12—H12 | 120.6 | C18—C113—C112 | 118.50 (18) |
C12—C13—C14 | 118.67 (19) | C18—C113—H113 | 120.7 |
C12—C13—H13 | 120.7 | C112—C113—H113 | 120.7 |
| | | |
C16—N12—N13—C17 | −0.4 (2) | N11—C15—C16—N14 | 22.0 (3) |
C17—S1—C1—C2 | −175.66 (15) | C14—C15—C16—N14 | −159.50 (18) |
C3—O2—C2—O1 | −6.4 (3) | N12—N13—C17—N14 | 0.6 (2) |
C3—O2—C2—C1 | 173.89 (18) | N12—N13—C17—S1 | −179.63 (15) |
S1—C1—C2—O1 | 168.67 (18) | C16—N14—C17—N13 | −0.6 (2) |
S1—C1—C2—O2 | −11.6 (2) | C18—N14—C17—N13 | 175.96 (17) |
C15—N11—C11—C12 | −0.7 (3) | C16—N14—C17—S1 | 179.61 (14) |
N11—C11—C12—C13 | −0.6 (3) | C18—N14—C17—S1 | −3.8 (3) |
C11—C12—C13—C14 | 1.2 (3) | C1—S1—C17—N13 | 5.5 (2) |
C12—C13—C14—C15 | −0.5 (3) | C1—S1—C17—N14 | −174.82 (16) |
C11—N11—C15—C14 | 1.4 (3) | C17—N14—C18—C19 | 71.1 (2) |
C11—N11—C15—C16 | 179.86 (17) | C16—N14—C18—C19 | −113.3 (2) |
C13—C14—C15—N11 | −0.9 (3) | C17—N14—C18—C113 | −106.7 (2) |
C13—C14—C15—C16 | −179.26 (17) | C16—N14—C18—C113 | 69.0 (3) |
N13—N12—C16—N14 | 0.0 (2) | C113—C18—C19—C110 | −0.9 (3) |
N13—N12—C16—C15 | 177.35 (17) | N14—C18—C19—C110 | −178.61 (17) |
C17—N14—C16—N12 | 0.4 (2) | C18—C19—C110—C111 | 0.8 (3) |
C18—N14—C16—N12 | −175.92 (18) | C19—C110—C111—C112 | −0.4 (3) |
C17—N14—C16—C15 | −176.91 (18) | C110—C111—C112—C113 | −0.1 (3) |
C18—N14—C16—C15 | 6.8 (3) | C19—C18—C113—C112 | 0.5 (3) |
N11—C15—C16—N12 | −154.95 (19) | N14—C18—C113—C112 | 178.18 (16) |
C14—C15—C16—N12 | 23.5 (3) | C111—C112—C113—C18 | 0.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···S1i | 0.95 | 2.99 | 3.757 (2) | 138 |
C11—H11···O2i | 0.95 | 2.48 | 3.399 (2) | 163 |
C19—H19···N11ii | 0.95 | 2.62 | 3.538 (3) | 162 |
C113—H113···S1iii | 0.95 | 2.92 | 3.835 (2) | 162 |
Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) x−1, y, z; (iii) x+1, y, z. |
Bis(methanol-
κO)bis(methyl
2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl-
κ2N
1,N
5]sulfanyl}acetato)zinc(II)/cadmium(II)
hexabromidocadmiate(II) (Compound_3)
top
Crystal data top
[Zn0.76Cd0.24(C16H14N4O2S)2(CH4O)2][Cd2Br6] | F(000) = 1433 |
Mr = 1497.85 | Dx = 2.090 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.4980 (3) Å | Cell parameters from 9550 reflections |
b = 13.7848 (4) Å | θ = 2.3–28.9° |
c = 15.0417 (4) Å | µ = 6.55 mm−1 |
β = 93.4660 (14)° | T = 100 K |
V = 2379.71 (11) Å3 | Plate, colourless |
Z = 2 | 0.60 × 0.45 × 0.02 mm |
Data collection top
Bruker AXS X8 APEXII CCD diffractometer | 6660 independent reflections |
Radiation source: sealed x-ray tube | 4673 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.079 |
φ or ω oscillation scans | θmax = 29.6°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −15→15 |
Tmin = 0.489, Tmax = 1.000 | k = −19→19 |
38522 measured reflections | l = −17→20 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0251P)2] where P = (Fo2 + 2Fc2)/3 |
6660 reflections | (Δ/σ)max = 0.001 |
269 parameters | Δρmax = 0.85 e Å−3 |
0 restraints | Δρmin = −0.94 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zn1 | 0.500000 | 0.000000 | 0.000000 | 0.01515 (19) | 0.758 (5) |
Cd1 | 0.500000 | 0.000000 | 0.000000 | 0.01515 (19) | 0.242 (5) |
S1 | 0.77304 (9) | 0.34141 (6) | 0.12561 (7) | 0.0202 (2) | |
O10 | 0.4252 (3) | −0.0060 (2) | 0.13714 (18) | 0.0341 (8) | |
H10 | 0.448328 | 0.032990 | 0.170487 | 0.051* | |
O11 | 0.5236 (3) | 0.3933 (2) | 0.15799 (18) | 0.0251 (7) | |
O12 | 0.4661 (3) | 0.39283 (18) | 0.01233 (18) | 0.0240 (7) | |
N11 | 0.6465 (3) | −0.0854 (2) | 0.0473 (2) | 0.0217 (8) | |
N12 | 0.6192 (3) | 0.1047 (2) | 0.0487 (2) | 0.0171 (7) | |
N13 | 0.6213 (3) | 0.2045 (2) | 0.0576 (2) | 0.0182 (7) | |
N14 | 0.7896 (3) | 0.1439 (2) | 0.1121 (2) | 0.0167 (7) | |
C1 | 0.6691 (4) | 0.4092 (3) | 0.0549 (3) | 0.0200 (9) | |
H1A | 0.688273 | 0.478946 | 0.061059 | 0.024* | |
H1B | 0.680477 | 0.390725 | −0.007604 | 0.024* | |
C2 | 0.5419 (4) | 0.3967 (2) | 0.0715 (3) | 0.0199 (9) | |
C3 | 0.4027 (4) | 0.3824 (4) | 0.1783 (3) | 0.0381 (12) | |
H3A | 0.396820 | 0.382425 | 0.242997 | 0.057* | |
H3B | 0.372127 | 0.321043 | 0.153538 | 0.057* | |
H3C | 0.357305 | 0.436484 | 0.151971 | 0.057* | |
C10 | 0.3908 (6) | −0.0943 (4) | 0.1762 (3) | 0.065 (2) | |
H10A | 0.342665 | −0.131861 | 0.132631 | 0.098* | |
H10B | 0.345851 | −0.080203 | 0.228019 | 0.098* | |
H10C | 0.460332 | −0.131826 | 0.195197 | 0.098* | |
C11 | 0.6506 (4) | −0.1826 (3) | 0.0475 (2) | 0.0234 (10) | |
H11 | 0.587251 | −0.217520 | 0.019527 | 0.028* | |
C12 | 0.7431 (4) | −0.2333 (3) | 0.0885 (3) | 0.0258 (10) | |
H12 | 0.745740 | −0.302138 | 0.085987 | 0.031* | |
C13 | 0.8306 (4) | −0.1829 (3) | 0.1321 (3) | 0.0256 (10) | |
H13 | 0.893143 | −0.216495 | 0.162721 | 0.031* | |
C14 | 0.8301 (4) | −0.0820 (3) | 0.1320 (3) | 0.0233 (9) | |
H14 | 0.891229 | −0.045496 | 0.161237 | 0.028* | |
C15 | 0.7364 (4) | −0.0358 (3) | 0.0879 (2) | 0.0164 (8) | |
C16 | 0.7186 (4) | 0.0699 (3) | 0.0826 (2) | 0.0171 (8) | |
C17 | 0.7228 (4) | 0.2257 (3) | 0.0950 (2) | 0.0174 (8) | |
C18 | 0.9090 (4) | 0.1408 (2) | 0.1471 (2) | 0.0180 (8) | |
C19 | 0.9332 (4) | 0.1493 (3) | 0.2374 (3) | 0.0294 (10) | |
H19 | 0.872174 | 0.157110 | 0.276606 | 0.035* | |
C20 | 1.0494 (4) | 0.1461 (3) | 0.2702 (3) | 0.0334 (11) | |
H20 | 1.068378 | 0.152769 | 0.332295 | 0.040* | |
C21 | 1.1369 (4) | 0.1328 (3) | 0.2127 (3) | 0.0342 (11) | |
H21 | 1.215790 | 0.129616 | 0.235204 | 0.041* | |
C22 | 1.1092 (4) | 0.1233 (3) | 0.1223 (3) | 0.0355 (11) | |
H22 | 1.169902 | 0.114705 | 0.082892 | 0.043* | |
C23 | 0.9953 (4) | 0.1279 (3) | 0.0888 (3) | 0.0264 (10) | |
H23 | 0.976197 | 0.122698 | 0.026654 | 0.032* | |
Cd2 | 0.48227 (3) | 0.08742 (2) | 0.41269 (2) | 0.01909 (8) | |
Br1 | 0.61550 (4) | 0.08350 (3) | 0.56277 (3) | 0.02167 (10) | |
Br2 | 0.62304 (4) | 0.06477 (3) | 0.28796 (2) | 0.02064 (10) | |
Br3 | 0.34955 (4) | 0.23155 (3) | 0.39011 (3) | 0.02446 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0148 (3) | 0.0112 (3) | 0.0191 (3) | −0.0014 (2) | −0.0022 (2) | 0.0000 (2) |
Cd1 | 0.0148 (3) | 0.0112 (3) | 0.0191 (3) | −0.0014 (2) | −0.0022 (2) | 0.0000 (2) |
S1 | 0.0216 (6) | 0.0128 (5) | 0.0263 (5) | 0.0002 (4) | 0.0012 (4) | −0.0007 (4) |
O10 | 0.040 (2) | 0.0345 (18) | 0.0278 (17) | −0.0142 (15) | 0.0005 (15) | −0.0054 (13) |
O11 | 0.0203 (17) | 0.0330 (16) | 0.0222 (16) | 0.0012 (13) | 0.0031 (13) | 0.0010 (12) |
O12 | 0.0267 (18) | 0.0176 (14) | 0.0267 (17) | −0.0005 (12) | −0.0075 (14) | 0.0041 (11) |
N11 | 0.036 (2) | 0.0127 (16) | 0.0171 (17) | 0.0001 (15) | 0.0033 (16) | 0.0002 (12) |
N12 | 0.0189 (19) | 0.0100 (15) | 0.0227 (18) | 0.0026 (13) | 0.0037 (15) | 0.0031 (12) |
N13 | 0.021 (2) | 0.0095 (15) | 0.0238 (18) | −0.0001 (13) | 0.0019 (15) | −0.0001 (12) |
N14 | 0.0197 (19) | 0.0115 (15) | 0.0192 (17) | 0.0024 (13) | 0.0034 (14) | 0.0002 (12) |
C1 | 0.027 (3) | 0.0126 (19) | 0.021 (2) | 0.0014 (16) | 0.0027 (18) | 0.0025 (14) |
C2 | 0.027 (3) | 0.0054 (17) | 0.028 (2) | 0.0006 (16) | 0.0030 (19) | 0.0023 (15) |
C3 | 0.025 (3) | 0.053 (3) | 0.038 (3) | −0.004 (2) | 0.010 (2) | 0.003 (2) |
C10 | 0.099 (5) | 0.072 (4) | 0.026 (3) | −0.061 (4) | 0.005 (3) | −0.002 (2) |
C11 | 0.042 (3) | 0.013 (2) | 0.015 (2) | −0.0037 (18) | 0.0052 (19) | −0.0023 (14) |
C12 | 0.037 (3) | 0.0117 (19) | 0.030 (2) | 0.0057 (18) | 0.011 (2) | 0.0021 (16) |
C13 | 0.032 (3) | 0.019 (2) | 0.026 (2) | 0.0137 (19) | 0.0077 (19) | 0.0082 (17) |
C14 | 0.028 (3) | 0.016 (2) | 0.027 (2) | 0.0057 (17) | 0.0074 (19) | 0.0046 (16) |
C15 | 0.023 (2) | 0.0125 (18) | 0.0148 (19) | 0.0030 (16) | 0.0063 (17) | 0.0022 (14) |
C16 | 0.023 (2) | 0.016 (2) | 0.0125 (19) | −0.0013 (16) | 0.0056 (16) | 0.0003 (14) |
C17 | 0.020 (2) | 0.0147 (19) | 0.017 (2) | 0.0021 (16) | 0.0043 (17) | 0.0021 (14) |
C18 | 0.020 (2) | 0.0106 (18) | 0.023 (2) | 0.0003 (16) | −0.0001 (17) | 0.0034 (15) |
C19 | 0.032 (3) | 0.034 (3) | 0.023 (2) | 0.006 (2) | 0.002 (2) | −0.0090 (18) |
C20 | 0.033 (3) | 0.038 (3) | 0.028 (3) | 0.006 (2) | −0.005 (2) | −0.0104 (19) |
C21 | 0.027 (3) | 0.037 (3) | 0.037 (3) | 0.007 (2) | −0.007 (2) | 0.000 (2) |
C22 | 0.027 (3) | 0.044 (3) | 0.036 (3) | 0.001 (2) | 0.005 (2) | 0.007 (2) |
C23 | 0.024 (3) | 0.033 (2) | 0.022 (2) | 0.0030 (19) | 0.0042 (19) | 0.0034 (17) |
Cd2 | 0.02020 (18) | 0.02010 (16) | 0.01703 (16) | −0.00016 (12) | 0.00158 (12) | 0.00235 (11) |
Br1 | 0.0228 (2) | 0.0231 (2) | 0.0188 (2) | −0.00628 (17) | −0.00146 (17) | 0.00207 (15) |
Br2 | 0.0257 (2) | 0.0195 (2) | 0.0172 (2) | −0.00333 (17) | 0.00451 (17) | −0.00214 (14) |
Br3 | 0.0245 (3) | 0.0241 (2) | 0.0248 (2) | 0.00462 (18) | 0.00164 (18) | 0.00229 (16) |
Geometric parameters (Å, º) top
Zn1—N12 | 2.092 (3) | C3—H3A | 0.9799 |
Zn1—N12i | 2.092 (3) | C3—H3B | 0.9801 |
Zn1—N11 | 2.141 (3) | C3—H3C | 0.9801 |
Zn1—N11i | 2.141 (3) | C10—H10A | 0.9801 |
Zn1—O10i | 2.284 (3) | C10—H10B | 0.9799 |
Zn1—O10 | 2.284 (3) | C10—H10C | 0.9802 |
Cd1—N12 | 2.092 (3) | C11—C12 | 1.387 (6) |
Cd1—N12i | 2.092 (3) | C11—H11 | 0.9502 |
Cd1—N11 | 2.141 (3) | C12—C13 | 1.358 (6) |
Cd1—N11i | 2.141 (3) | C12—H12 | 0.9501 |
Cd1—O10i | 2.284 (3) | C13—C14 | 1.391 (5) |
Cd1—O10 | 2.284 (3) | C13—H13 | 0.9502 |
S1—C17 | 1.749 (4) | C14—C15 | 1.386 (6) |
S1—C1 | 1.811 (4) | C14—H14 | 0.9502 |
O10—C10 | 1.418 (5) | C15—C16 | 1.473 (5) |
O10—H10 | 0.7717 | C18—C23 | 1.375 (5) |
O11—C2 | 1.332 (5) | C18—C19 | 1.375 (5) |
O11—C3 | 1.449 (5) | C19—C20 | 1.397 (6) |
O12—C2 | 1.208 (5) | C19—H19 | 0.9499 |
N11—C11 | 1.340 (4) | C20—C21 | 1.378 (6) |
N11—C15 | 1.354 (5) | C20—H20 | 0.9500 |
N12—C16 | 1.314 (5) | C21—C22 | 1.384 (6) |
N12—N13 | 1.382 (4) | C21—H21 | 0.9502 |
N13—C17 | 1.298 (5) | C22—C23 | 1.376 (6) |
N14—C16 | 1.364 (5) | C22—H22 | 0.9500 |
N14—C17 | 1.379 (5) | C23—H23 | 0.9500 |
N14—C18 | 1.441 (5) | Cd2—Br3 | 2.5157 (5) |
C1—C2 | 1.508 (6) | Cd2—Br2 | 2.5699 (5) |
C1—H1A | 0.9901 | Cd2—Br1ii | 2.6461 (5) |
C1—H1B | 0.9899 | Cd2—Br1 | 2.6508 (5) |
| | | |
N12—Zn1—N12i | 180.0 | O11—C2—C1 | 112.2 (4) |
N12—Zn1—N11 | 77.15 (12) | O11—C3—H3A | 109.5 |
N12i—Zn1—N11 | 102.85 (12) | O11—C3—H3B | 109.6 |
N12—Zn1—N11i | 102.85 (12) | H3A—C3—H3B | 109.5 |
N12i—Zn1—N11i | 77.15 (12) | O11—C3—H3C | 109.3 |
N11—Zn1—N11i | 180.0 | H3A—C3—H3C | 109.5 |
N12—Zn1—O10i | 90.97 (11) | H3B—C3—H3C | 109.5 |
N12i—Zn1—O10i | 89.03 (11) | O10—C10—H10A | 109.7 |
N11—Zn1—O10i | 89.34 (11) | O10—C10—H10B | 109.5 |
N11i—Zn1—O10i | 90.66 (11) | H10A—C10—H10B | 109.5 |
N12—Zn1—O10 | 89.03 (11) | O10—C10—H10C | 109.3 |
N12i—Zn1—O10 | 90.97 (11) | H10A—C10—H10C | 109.5 |
N11—Zn1—O10 | 90.66 (11) | H10B—C10—H10C | 109.5 |
N11i—Zn1—O10 | 89.34 (11) | N11—C11—C12 | 122.1 (4) |
O10i—Zn1—O10 | 180.0 | N11—C11—H11 | 118.6 |
N12—Cd1—N12i | 180.0 | C12—C11—H11 | 119.2 |
N12—Cd1—N11 | 77.15 (12) | C13—C12—C11 | 118.9 (4) |
N12i—Cd1—N11 | 102.85 (12) | C13—C12—H12 | 120.4 |
N12—Cd1—N11i | 102.85 (12) | C11—C12—H12 | 120.7 |
N12i—Cd1—N11i | 77.15 (12) | C12—C13—C14 | 120.5 (4) |
N11—Cd1—N11i | 180.0 | C12—C13—H13 | 120.1 |
N12—Cd1—O10i | 90.97 (11) | C14—C13—H13 | 119.4 |
N12i—Cd1—O10i | 89.03 (11) | C15—C14—C13 | 117.6 (4) |
N11—Cd1—O10i | 89.34 (11) | C15—C14—H14 | 120.6 |
N11i—Cd1—O10i | 90.66 (11) | C13—C14—H14 | 121.8 |
N12—Cd1—O10 | 89.03 (11) | N11—C15—C14 | 122.3 (3) |
N12i—Cd1—O10 | 90.97 (11) | N11—C15—C16 | 112.0 (3) |
N11—Cd1—O10 | 90.66 (11) | C14—C15—C16 | 125.6 (4) |
N11i—Cd1—O10 | 89.34 (11) | N12—C16—N14 | 110.0 (3) |
O10i—Cd1—O10 | 180.0 | N12—C16—C15 | 119.8 (3) |
C17—S1—C1 | 96.91 (18) | N14—C16—C15 | 130.1 (4) |
C10—O10—Zn1 | 122.4 (3) | N13—C17—N14 | 111.9 (3) |
C10—O10—Cd1 | 122.4 (3) | N13—C17—S1 | 126.4 (3) |
C10—O10—H10 | 115.0 | N14—C17—S1 | 121.7 (3) |
Zn1—O10—H10 | 115.3 | C23—C18—C19 | 122.0 (4) |
Cd1—O10—H10 | 115.3 | C23—C18—N14 | 118.6 (3) |
C2—O11—C3 | 114.8 (3) | C19—C18—N14 | 119.3 (4) |
C11—N11—C15 | 118.5 (3) | C18—C19—C20 | 118.6 (4) |
C11—N11—Cd1 | 125.3 (3) | C18—C19—H19 | 120.7 |
C15—N11—Cd1 | 115.9 (2) | C20—C19—H19 | 120.7 |
C11—N11—Zn1 | 125.3 (3) | C21—C20—C19 | 120.0 (4) |
C15—N11—Zn1 | 115.9 (2) | C21—C20—H20 | 119.8 |
C16—N12—N13 | 108.4 (3) | C19—C20—H20 | 120.2 |
C16—N12—Zn1 | 114.8 (2) | C20—C21—C22 | 119.8 (5) |
N13—N12—Zn1 | 136.7 (2) | C20—C21—H21 | 120.0 |
C16—N12—Cd1 | 114.8 (2) | C22—C21—H21 | 120.2 |
N13—N12—Cd1 | 136.7 (2) | C23—C22—C21 | 120.8 (5) |
C17—N13—N12 | 106.0 (3) | C23—C22—H22 | 119.8 |
C16—N14—C17 | 103.6 (3) | C21—C22—H22 | 119.4 |
C16—N14—C18 | 129.5 (3) | C18—C23—C22 | 118.7 (4) |
C17—N14—C18 | 126.8 (3) | C18—C23—H23 | 120.3 |
C2—C1—S1 | 117.2 (3) | C22—C23—H23 | 121.0 |
C2—C1—H1A | 107.9 | Br3—Cd2—Br2 | 113.643 (16) |
S1—C1—H1A | 108.1 | Br3—Cd2—Br1ii | 117.563 (18) |
C2—C1—H1B | 108.2 | Br2—Cd2—Br1ii | 106.577 (15) |
S1—C1—H1B | 107.8 | Br3—Cd2—Br1 | 116.462 (16) |
H1A—C1—H1B | 107.3 | Br2—Cd2—Br1 | 105.201 (17) |
O12—C2—O11 | 124.6 (4) | Br1ii—Cd2—Br1 | 95.255 (14) |
O12—C2—C1 | 123.1 (4) | Cd2ii—Br1—Cd2 | 84.745 (14) |
| | | |
C16—N12—N13—C17 | 1.1 (4) | C17—N14—C16—N12 | 1.5 (4) |
Zn1—N12—N13—C17 | 179.1 (3) | C18—N14—C16—N12 | −174.5 (3) |
Cd1—N12—N13—C17 | 179.1 (3) | C17—N14—C16—C15 | −175.3 (4) |
C17—S1—C1—C2 | 61.4 (3) | C18—N14—C16—C15 | 8.7 (6) |
C3—O11—C2—O12 | 1.1 (5) | N11—C15—C16—N12 | 6.0 (5) |
C3—O11—C2—C1 | 179.4 (3) | C14—C15—C16—N12 | −171.2 (4) |
S1—C1—C2—O12 | −141.3 (3) | N11—C15—C16—N14 | −177.5 (4) |
S1—C1—C2—O11 | 40.4 (4) | C14—C15—C16—N14 | 5.4 (6) |
C15—N11—C11—C12 | 0.5 (6) | N12—N13—C17—N14 | −0.2 (4) |
Cd1—N11—C11—C12 | −172.3 (3) | N12—N13—C17—S1 | −178.0 (3) |
Zn1—N11—C11—C12 | −172.3 (3) | C16—N14—C17—N13 | −0.8 (4) |
N11—C11—C12—C13 | 2.1 (6) | C18—N14—C17—N13 | 175.3 (3) |
C11—C12—C13—C14 | −3.0 (6) | C16—N14—C17—S1 | 177.2 (3) |
C12—C13—C14—C15 | 1.4 (6) | C18—N14—C17—S1 | −6.7 (5) |
C11—N11—C15—C14 | −2.2 (5) | C1—S1—C17—N13 | −19.3 (4) |
Cd1—N11—C15—C14 | 171.3 (3) | C1—S1—C17—N14 | 163.0 (3) |
Zn1—N11—C15—C14 | 171.3 (3) | C16—N14—C18—C23 | 75.7 (5) |
C11—N11—C15—C16 | −179.5 (3) | C17—N14—C18—C23 | −99.5 (4) |
Cd1—N11—C15—C16 | −5.9 (4) | C16—N14—C18—C19 | −103.3 (4) |
Zn1—N11—C15—C16 | −5.9 (4) | C17—N14—C18—C19 | 81.6 (5) |
C13—C14—C15—N11 | 1.3 (6) | C23—C18—C19—C20 | 1.1 (6) |
C13—C14—C15—C16 | 178.2 (4) | N14—C18—C19—C20 | 180.0 (3) |
N13—N12—C16—N14 | −1.7 (4) | C18—C19—C20—C21 | −1.3 (6) |
Zn1—N12—C16—N14 | 179.9 (2) | C19—C20—C21—C22 | 0.4 (7) |
Cd1—N12—C16—N14 | 179.9 (2) | C20—C21—C22—C23 | 0.7 (7) |
N13—N12—C16—C15 | 175.5 (3) | C19—C18—C23—C22 | 0.0 (6) |
Zn1—N12—C16—C15 | −3.0 (4) | N14—C18—C23—C22 | −178.9 (4) |
Cd1—N12—C16—C15 | −3.0 (4) | C21—C22—C23—C18 | −0.9 (6) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10···Br2 | 0.77 | 2.63 | 3.263 (3) | 141 |
C1—H1B···Br3iii | 0.99 | 3.06 | 3.851 (4) | 138 |
C3—H3A···Br3 | 0.98 | 3.11 | 3.884 (5) | 137 |
C3—H3C···Br1iv | 0.98 | 3.03 | 3.668 (5) | 124 |
C10—H10A···Br3v | 0.98 | 2.91 | 3.750 (5) | 145 |
C11—H11···O12i | 0.95 | 2.53 | 3.296 (5) | 138 |
C11—H11···N13i | 0.95 | 2.61 | 3.431 (6) | 145 |
C12—H12···Br2vi | 0.95 | 2.98 | 3.636 (4) | 127 |
Symmetry codes: (i) −x+1, −y, −z; (iii) x+1/2, −y+1/2, z−1/2; (iv) x−1/2, −y+1/2, z−1/2; (v) −x+1/2, y−1/2, −z+1/2; (vi) −x+3/2, y−1/2, −z+1/2. |
Dichlorido(methyl
2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl-
κ2N
1,N
5]sulfanyl}acetato)mercury(II) (Compound_4)
top
Crystal data top
[HgCl2(C16H14N4O2S)] | Z = 2 |
Mr = 597.86 | F(000) = 568 |
Triclinic, P1 | Dx = 2.068 Mg m−3 |
a = 8.5198 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.4709 (3) Å | Cell parameters from 1863 reflections |
c = 13.9682 (7) Å | θ = 2.5–23.3° |
α = 105.050 (3)° | µ = 8.42 mm−1 |
β = 95.083 (3)° | T = 100 K |
γ = 115.081 (2)° | Prism, colourless |
V = 960.04 (7) Å3 | 0.08 × 0.04 × 0.03 mm |
Data collection top
Bruker X8 KappaAPEXII CCD diffractometer | 3341 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
ω and phi scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: multi-scan SADABS | h = −10→10 |
Tmin = 0.656, Tmax = 1.000 | k = −11→11 |
21983 measured reflections | l = 0→17 |
3765 independent reflections | |
Refinement top
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: difference Fourier map |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0212P)2 + 3.2485P] where P = (Fo2 + 2Fc2)/3 |
3765 reflections | (Δ/σ)max = 0.002 |
236 parameters | Δρmax = 1.83 e Å−3 |
0 restraints | Δρmin = −1.15 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Hg1 | 0.80705 (3) | 1.28547 (2) | 0.38893 (2) | 0.02077 (7) | |
Cl1 | 0.77534 (17) | 1.49373 (15) | 0.50670 (10) | 0.0263 (3) | |
Cl2 | 0.89922 (18) | 1.19938 (19) | 0.24002 (11) | 0.0355 (3) | |
S1 | 0.27962 (19) | 0.63277 (16) | 0.06736 (10) | 0.0282 (3) | |
O1 | −0.0199 (5) | 0.6971 (5) | 0.1261 (3) | 0.0315 (9) | |
O2 | −0.0380 (6) | 0.8222 (5) | 0.0114 (3) | 0.0432 (11) | |
N11 | 0.7903 (5) | 1.0968 (5) | 0.4808 (3) | 0.0202 (9) | |
N12 | 0.5208 (5) | 1.0074 (5) | 0.3150 (3) | 0.0210 (9) | |
N13 | 0.4136 (6) | 0.9344 (5) | 0.2172 (3) | 0.0215 (9) | |
N14 | 0.4766 (5) | 0.7521 (5) | 0.2602 (3) | 0.0181 (9) | |
C1 | 0.1837 (7) | 0.7405 (7) | 0.0148 (4) | 0.0264 (12) | |
H1A | 0.2780 | 0.8535 | 0.0255 | 0.032* | |
H1B | 0.1382 | 0.6832 | −0.0595 | 0.032* | |
C2 | 0.0355 (7) | 0.7516 (6) | 0.0604 (4) | 0.0242 (12) | |
C3 | −0.2014 (10) | 0.8255 (9) | 0.0422 (6) | 0.0533 (19) | |
H3A | −0.2945 | 0.7122 | 0.0281 | 0.080* | |
H3B | −0.2439 | 0.8800 | 0.0034 | 0.080* | |
H3C | −0.1723 | 0.8864 | 0.1151 | 0.080* | |
C11 | 0.8941 (7) | 1.1437 (6) | 0.5731 (4) | 0.0248 (12) | |
H11 | 0.9773 | 1.2570 | 0.6049 | 0.030* | |
C12 | 0.8844 (7) | 1.0334 (7) | 0.6235 (4) | 0.0260 (12) | |
H12 | 0.9580 | 1.0706 | 0.6892 | 0.031* | |
C13 | 0.7664 (7) | 0.8689 (6) | 0.5769 (4) | 0.0251 (12) | |
H13 | 0.7592 | 0.7904 | 0.6093 | 0.030* | |
C14 | 0.6572 (7) | 0.8188 (6) | 0.4813 (4) | 0.0233 (12) | |
H14 | 0.5743 | 0.7060 | 0.4477 | 0.028* | |
C15 | 0.6719 (6) | 0.9355 (6) | 0.4369 (4) | 0.0174 (10) | |
C16 | 0.5575 (6) | 0.8987 (6) | 0.3391 (4) | 0.0164 (10) | |
C17 | 0.3903 (7) | 0.7813 (6) | 0.1865 (4) | 0.0197 (11) | |
C18 | 0.4932 (7) | 0.6027 (6) | 0.2462 (4) | 0.0192 (11) | |
C19 | 0.6528 (7) | 0.6062 (6) | 0.2321 (4) | 0.0208 (11) | |
H19 | 0.7509 | 0.7061 | 0.2345 | 0.025* | |
C110 | 0.6686 (8) | 0.4627 (7) | 0.2145 (4) | 0.0281 (13) | |
H110 | 0.7788 | 0.4644 | 0.2063 | 0.034* | |
C111 | 0.5249 (8) | 0.3172 (6) | 0.2088 (4) | 0.0268 (12) | |
H111 | 0.5358 | 0.2187 | 0.1963 | 0.032* | |
C112 | 0.3632 (8) | 0.3148 (6) | 0.2213 (4) | 0.0262 (12) | |
H112 | 0.2636 | 0.2140 | 0.2159 | 0.031* | |
C113 | 0.3473 (7) | 0.4582 (6) | 0.2415 (4) | 0.0242 (12) | |
H113 | 0.2385 | 0.4578 | 0.2521 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Hg1 | 0.02498 (12) | 0.01219 (10) | 0.01726 (11) | 0.00464 (8) | 0.00269 (8) | 0.00031 (7) |
Cl1 | 0.0251 (7) | 0.0160 (6) | 0.0271 (7) | 0.0061 (5) | 0.0043 (6) | −0.0031 (5) |
Cl2 | 0.0265 (7) | 0.0447 (9) | 0.0218 (7) | 0.0109 (7) | 0.0069 (6) | −0.0007 (6) |
S1 | 0.0336 (8) | 0.0212 (7) | 0.0190 (7) | 0.0097 (6) | −0.0030 (6) | −0.0019 (6) |
O1 | 0.024 (2) | 0.034 (2) | 0.023 (2) | 0.0027 (18) | 0.0031 (17) | 0.0072 (18) |
O2 | 0.055 (3) | 0.046 (3) | 0.044 (3) | 0.036 (2) | 0.021 (2) | 0.017 (2) |
N11 | 0.022 (2) | 0.013 (2) | 0.019 (2) | 0.0031 (18) | 0.0030 (18) | 0.0031 (18) |
N12 | 0.014 (2) | 0.015 (2) | 0.024 (2) | 0.0007 (18) | −0.0009 (18) | 0.0026 (18) |
N13 | 0.022 (2) | 0.013 (2) | 0.016 (2) | 0.0039 (18) | −0.0033 (18) | −0.0049 (18) |
N14 | 0.021 (2) | 0.012 (2) | 0.017 (2) | 0.0049 (18) | 0.0050 (18) | 0.0021 (17) |
C1 | 0.029 (3) | 0.027 (3) | 0.017 (3) | 0.010 (3) | 0.001 (2) | 0.005 (2) |
C2 | 0.028 (3) | 0.013 (2) | 0.021 (3) | 0.003 (2) | 0.004 (2) | 0.001 (2) |
C3 | 0.056 (5) | 0.051 (4) | 0.056 (5) | 0.026 (4) | 0.010 (4) | 0.019 (4) |
C11 | 0.025 (3) | 0.016 (3) | 0.022 (3) | 0.003 (2) | 0.001 (2) | 0.001 (2) |
C12 | 0.026 (3) | 0.027 (3) | 0.020 (3) | 0.009 (2) | 0.004 (2) | 0.006 (2) |
C13 | 0.032 (3) | 0.019 (3) | 0.020 (3) | 0.009 (2) | 0.008 (2) | 0.005 (2) |
C14 | 0.029 (3) | 0.013 (2) | 0.021 (3) | 0.007 (2) | 0.007 (2) | 0.001 (2) |
C15 | 0.018 (3) | 0.017 (2) | 0.015 (3) | 0.006 (2) | 0.006 (2) | 0.003 (2) |
C16 | 0.012 (2) | 0.012 (2) | 0.021 (3) | 0.0012 (19) | 0.005 (2) | 0.004 (2) |
C17 | 0.017 (3) | 0.016 (2) | 0.021 (3) | 0.003 (2) | 0.004 (2) | 0.007 (2) |
C18 | 0.028 (3) | 0.012 (2) | 0.012 (2) | 0.007 (2) | 0.004 (2) | −0.001 (2) |
C19 | 0.025 (3) | 0.015 (2) | 0.015 (3) | 0.004 (2) | 0.004 (2) | 0.003 (2) |
C110 | 0.036 (3) | 0.023 (3) | 0.027 (3) | 0.016 (3) | 0.008 (3) | 0.008 (2) |
C111 | 0.043 (3) | 0.017 (3) | 0.017 (3) | 0.013 (3) | 0.001 (2) | 0.002 (2) |
C112 | 0.036 (3) | 0.013 (2) | 0.018 (3) | 0.003 (2) | 0.003 (2) | 0.003 (2) |
C113 | 0.026 (3) | 0.021 (3) | 0.019 (3) | 0.005 (2) | 0.006 (2) | 0.005 (2) |
Geometric parameters (Å, º) top
Hg1—Cl1 | 2.3483 (12) | C3—H3C | 0.9800 |
Hg1—Cl2 | 2.3579 (14) | C11—C12 | 1.383 (7) |
Hg1—N11 | 2.423 (4) | C11—H11 | 0.9500 |
Hg1—N12 | 2.578 (4) | C12—C13 | 1.375 (7) |
S1—C17 | 1.738 (5) | C12—H12 | 0.9500 |
S1—C1 | 1.799 (5) | C13—C14 | 1.397 (7) |
O1—C2 | 1.203 (6) | C13—H13 | 0.9500 |
O2—C2 | 1.351 (7) | C14—C15 | 1.369 (7) |
O2—C3 | 1.503 (8) | C14—H14 | 0.9500 |
N11—C11 | 1.345 (7) | C15—C16 | 1.472 (7) |
N11—C15 | 1.350 (6) | C18—C19 | 1.379 (7) |
N12—C16 | 1.305 (6) | C18—C113 | 1.386 (7) |
N12—N13 | 1.391 (6) | C19—C110 | 1.383 (7) |
N13—C17 | 1.321 (6) | C19—H19 | 0.9500 |
N14—C17 | 1.364 (6) | C110—C111 | 1.379 (8) |
N14—C16 | 1.370 (6) | C110—H110 | 0.9500 |
N14—C18 | 1.446 (6) | C111—C112 | 1.395 (8) |
C1—C2 | 1.494 (8) | C111—H111 | 0.9500 |
C1—H1A | 0.9900 | C112—C113 | 1.381 (7) |
C1—H1B | 0.9900 | C112—H112 | 0.9500 |
C3—H3A | 0.9800 | C113—H113 | 0.9500 |
C3—H3B | 0.9800 | | |
| | | |
Cl1—Hg1—Cl2 | 148.93 (5) | C13—C12—C11 | 118.9 (5) |
Cl1—Hg1—N11 | 103.23 (10) | C13—C12—H12 | 120.6 |
Cl2—Hg1—N11 | 106.15 (11) | C11—C12—H12 | 120.6 |
Cl1—Hg1—N12 | 114.52 (10) | C12—C13—C14 | 119.1 (5) |
Cl2—Hg1—N12 | 86.27 (10) | C12—C13—H13 | 120.5 |
N11—Hg1—N12 | 67.54 (14) | C14—C13—H13 | 120.5 |
C17—S1—C1 | 98.7 (2) | C15—C14—C13 | 118.7 (5) |
C2—O2—C3 | 115.4 (5) | C15—C14—H14 | 120.6 |
C11—N11—C15 | 118.1 (4) | C13—C14—H14 | 120.6 |
C11—N11—Hg1 | 123.5 (3) | N11—C15—C14 | 122.7 (5) |
C15—N11—Hg1 | 118.5 (3) | N11—C15—C16 | 113.8 (4) |
C16—N12—N13 | 108.6 (4) | C14—C15—C16 | 123.5 (4) |
C16—N12—Hg1 | 106.3 (3) | N12—C16—N14 | 109.8 (4) |
N13—N12—Hg1 | 128.4 (3) | N12—C16—C15 | 123.2 (4) |
C17—N13—N12 | 105.8 (4) | N14—C16—C15 | 127.0 (4) |
C17—N14—C16 | 104.8 (4) | N13—C17—N14 | 111.0 (4) |
C17—N14—C18 | 124.4 (4) | N13—C17—S1 | 127.4 (4) |
C16—N14—C18 | 130.2 (4) | N14—C17—S1 | 121.5 (4) |
C2—C1—S1 | 113.4 (4) | C19—C18—C113 | 121.5 (5) |
C2—C1—H1A | 108.9 | C19—C18—N14 | 118.6 (4) |
S1—C1—H1A | 108.9 | C113—C18—N14 | 119.8 (5) |
C2—C1—H1B | 108.9 | C18—C19—C110 | 119.3 (5) |
S1—C1—H1B | 108.9 | C18—C19—H19 | 120.4 |
H1A—C1—H1B | 107.7 | C110—C19—H19 | 120.4 |
O1—C2—O2 | 124.0 (5) | C111—C110—C19 | 120.2 (5) |
O1—C2—C1 | 126.2 (5) | C111—C110—H110 | 119.9 |
O2—C2—C1 | 109.6 (5) | C19—C110—H110 | 119.9 |
O2—C3—H3A | 109.5 | C110—C111—C112 | 119.9 (5) |
O2—C3—H3B | 109.5 | C110—C111—H111 | 120.0 |
H3A—C3—H3B | 109.5 | C112—C111—H111 | 120.0 |
O2—C3—H3C | 109.5 | C113—C112—C111 | 120.3 (5) |
H3A—C3—H3C | 109.5 | C113—C112—H112 | 119.8 |
H3B—C3—H3C | 109.5 | C111—C112—H112 | 119.8 |
N11—C11—C12 | 122.5 (5) | C112—C113—C18 | 118.7 (5) |
N11—C11—H11 | 118.8 | C112—C113—H113 | 120.7 |
C12—C11—H11 | 118.8 | C18—C113—H113 | 120.7 |
| | | |
C16—N12—N13—C17 | 0.1 (5) | C18—N14—C16—C15 | −6.7 (8) |
Hg1—N12—N13—C17 | 130.2 (4) | N11—C15—C16—N12 | −25.5 (7) |
C17—S1—C1—C2 | −71.7 (4) | C14—C15—C16—N12 | 152.7 (5) |
C3—O2—C2—O1 | −1.6 (8) | N11—C15—C16—N14 | 153.4 (5) |
C3—O2—C2—C1 | 173.9 (5) | C14—C15—C16—N14 | −28.4 (8) |
S1—C1—C2—O1 | 0.2 (7) | N12—N13—C17—N14 | 0.4 (6) |
S1—C1—C2—O2 | −175.2 (4) | N12—N13—C17—S1 | −175.6 (4) |
C15—N11—C11—C12 | 0.4 (8) | C16—N14—C17—N13 | −0.6 (6) |
Hg1—N11—C11—C12 | −178.9 (4) | C18—N14—C17—N13 | −172.9 (4) |
N11—C11—C12—C13 | 1.1 (8) | C16—N14—C17—S1 | 175.6 (4) |
C11—C12—C13—C14 | −1.4 (8) | C18—N14—C17—S1 | 3.3 (7) |
C12—C13—C14—C15 | 0.2 (8) | C1—S1—C17—N13 | −9.1 (5) |
C11—N11—C15—C14 | −1.7 (7) | C1—S1—C17—N14 | 175.2 (4) |
Hg1—N11—C15—C14 | 177.6 (4) | C17—N14—C18—C19 | 102.5 (6) |
C11—N11—C15—C16 | 176.5 (4) | C16—N14—C18—C19 | −67.7 (7) |
Hg1—N11—C15—C16 | −4.2 (5) | C17—N14—C18—C113 | −74.0 (6) |
C13—C14—C15—N11 | 1.4 (8) | C16—N14—C18—C113 | 115.8 (6) |
C13—C14—C15—C16 | −176.6 (5) | C113—C18—C19—C110 | −0.9 (8) |
N13—N12—C16—N14 | −0.5 (5) | N14—C18—C19—C110 | −177.4 (4) |
Hg1—N12—C16—N14 | −141.8 (3) | C18—C19—C110—C111 | 1.4 (8) |
N13—N12—C16—C15 | 178.6 (4) | C19—C110—C111—C112 | −0.3 (8) |
Hg1—N12—C16—C15 | 37.3 (5) | C110—C111—C112—C113 | −1.3 (8) |
C17—N14—C16—N12 | 0.7 (5) | C111—C112—C113—C18 | 1.8 (8) |
C18—N14—C16—N12 | 172.3 (5) | C19—C18—C113—C112 | −0.7 (8) |
C17—N14—C16—C15 | −178.4 (5) | N14—C18—C113—C112 | 175.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3C···Cl2i | 0.98 | 2.79 | 3.583 (8) | 138 |
C19—H19···O1ii | 0.95 | 2.59 | 3.172 (6) | 120 |
C113—H113···Cl2iii | 0.95 | 2.84 | 3.551 (6) | 132 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x−1, y−1, z. |
Hydrogen-bond geometry (Å, °) for the compounds 1–4 topThe superscript letters refer to the symmetry codes shown also in the text and
figures. |
Compound | D—H···A | D—H | H···A | D···A | D—H···A | Symmetry code |
1 | N3A—H30A···S1Aa | 0.90 | 2.38 | 3.265 (2) | 168.4 | -x, -y, -z+1 |
| N3B—H30B···S1Bb | 0.83 | 2.47 | 3.285 (2) | 166.6 | -x+1, -y, -z+1 |
| C9A—H9A···S1Ac | 0.95 | 2.93 | 3.852 (2) | 163.1 | x, y+1, z |
| C9B—H9B···S1Bc | 0.95 | 2.81 | 3.738 (2) | 166.8 | x,y+1,z |
| | | | | | |
2 | C11—H11···S1a | 0.95 | 2.99 | 3.757 (2) | 138.4 | x+1, -y+1/2, z+1/2 |
| C11—H11···O2a | 0.95 | 2.48 | 3.399 (2) | 162.5 | x+1, -y+1/2, z+1/2 |
| C19—H19···N11b | 0.95 | 2.62 | 3.538 (3) | 162.0 | x-1, y, z |
| C113—H113···S1c | 0.95 | 2.92 | 3.835 (2) | 162.4 | x+1, y, z |
| | | | | | |
3 | O10—H10···Br2 | 0.77 | 2.63 | 3.263 (3) | 140.5 | |
| C1—H1B···Br3c | 0.99 | 3.06 | 3.851 (4) | 138.0 | x+1/2, -y+1/2, z-1/2 |
| C3—H3A···Br3 | 0.98 | 3.11 | 3.884 (5) | 137.1 | |
| C3—H3C···Br1d | 0.98 | 3.03 | 3.884 (5) | 124.2 | x-1/2, -y+1/2, z-1/2 |
| C10—H10A···Br3e | 0.98 | 2.91 | 3.750 (5) | 144.6 | -x+1/2, y-1/2, -z+1/2 |
| C11—H11···O12a | 0.95 | 2.53 | 3.296 (5) | 137.6 | -x+1, -y, -z |
| C11—H11···N13a | 0.95 | 2.61 | 3.431 (6) | 145.3 | -x+1, -y, -z |
| C12—H12···Br2f | 0.95 | 2.98 | 3.636 (4) | 127.2 | -x+3/2, y-1/2, -z+1/2 |
| | | | | | |
4 | C3—H3C···Cl2a | 0.98 | 2.79 | 3.583 (8) | 138.2 | x-1, y, z |
| C19—H19···O1b | 0.95 | 2.59 | 3.172 (6) | 119.9 | x+1, y, z |
| C113—H113···Cl2c | 0.95 | 2.84 | 3.551 (6) | 132.3 | x-1, y-1, z |
Intermolecular interaction parameters (Å, °) for compound 1 topX—Y···π interactions | Y···Cg | γ | X—Y···Cg | X···Cg' |
C113—H113···Cg2d | 2.69 | 11.35 | 151 | 3.555 |
C213—H213···Cg5d | 2.82 | 10.40 | 150 | 3.670 |
C17—S1···Cg2e | 3.66 | 12.04 | 163 | 5.298 |
C27—S2···Cg5e | 3.67 | 14.58 | 165 | 5.316 |
Cg2 is the centroid of the N11/C11–C15 ring and
Cg5 that of the N21/C21–C25 ring.
Symmetry codes:
(d) x, y-1, z;
(e) x, -y+1/2, z+1/2. |
Intermolecular interaction parameters (Å, °) for compound 2 topX—H···π interactions | H···Cg | γ | X—H···Cg | X···Cg' |
C12—H12···Cg3a | 2.76 | 8.47 | 143 | 3.562 |
C19—H19···Cg2b | 2.53 | 12.85 | 155 | 3.411 |
Cg2 is the centroid of the N11/C11–C15 ring and
Cg3 that of the C18/C19/C110–C113 ring.
Symmetry codes:
(a) x+1, -y+1/2, z+1/2;
(b) x-1, y, z. |
Selected geometric parameters (Å, °) for 3 and 4 top3 | | | | 4 | | | |
M1*—N12 | 2.092 (3) | N12—M1—N12a | 180.0 | Hg1—Cl1 | 2.3483 (12) | Cl1—Hg1—Cl2 | 148.93 (5) |
M1—N12a | 2.092 (3) | N12—M1—N11a | 102.85 (12) | Hg1—Cl2 | 2.3579 (14) | Cl1—Hg1—N11 | 103.23 (10) |
M1—N11a | 2.141 (3) | N12a—M1—N11a | 77.15 (12) | Hg1—N11 | 2.423 (4) | Cl2—Hg1—N11 | 106.15 (11) |
M1—N11 | 2.141 (3) | N12—M1—N11 | 77.15 (12) | Hg1—N12 | 2.578 (4) | Cl1—Hg1—N12 | 114.52 (10) |
M1—O10a | 2.284 (3) | N12a—M1—N11 | 102.85(12 | | | Cl2—Hg1—N12 | 86.27 (10) |
M1—O10 | 2.284 (3) | N11a—M1—N11 | 180.0 | | | N11—Hg1—N12 | 67.54 (14) |
Cd2—Br3 | 2.5157 (5) | N12—M1—O10a | 90.97 (11) | | | | |
Cd2—Br2 | 2.5699 (5) | N12a—M1—O10a | 89.03 (11) | | | | |
Cd2—Br1b | 2.6461 (5) | N11a—M1—O10a | 90.66 (11) | | | | |
Cd2—Br1 | 2.6508 (5) | N11—M1—O10a | 89.34 (11) | | | | |
Br1—Cd2b | 2.6461 (5) | N12—M1—O10 | 89.03 (11) | | | | |
M1—Cd2 | 6.3389 (4) | N12a—M1—O10 | 90.97 (11) | | | | |
Cd2—Cd2b | 3.5698 (5) | N11a—M1—O10 | 89.34 (11) | | | | |
Br1—Br1b | 3.9132 (8) | N11—M1—O10 | 90.66 (11) | | | | |
| | O10a—M1—O10 | 180.0 | | | | |
| | Br3—Cd2—Br2 | 113.643 (16) | | | | |
| | Br3—Cd2—Br1b | 117.563 (18) | | | | |
| | Br2—Cd2—Br1b | 106.577 (15) | | | | |
| | Br3—Cd2—Br1 | 116.462 (16) | | | | |
| | Br2—Cd2—Br1 | 105.201 (17) | | | | |
| | Br1b—Cd2—Br1 | 95.255 (14) | | | | |
| | Cd2b—Br1—Cd2 | 84.745 (14) | | | | |
Note: (*) M = 0.76Zn/0.24Cd;
Symmetry codes:
(a) -x+1, -y, -z;
(b) -x+1, -y, -z+1. |
Intermolecular interaction parameters (Å, °) for compound 3 topX—Y···π interactions | Y···Cg | γ | X—Y···Cg | X···Cg' |
C14—H14···Cg5 | 2.93 | 28.66 | 149 | 3.774 |
C22—H22···Cg4c | 2.85 | 8.62 | 151 | 3.710 |
Cd2—Br2···Cg1 | 3.629 | 24.21 | 144.79 | 5.919 |
Cd2—Br2···Cg1b | 3.629 | 24.21 | 144.79 | 5.919 |
Cd2—Br2···Cg3 | 3.496 | 17.17 | 143.81 | 5.775 |
Cd2—Br3···Cg3d | 3.816 | 22.78 | 122.99 | 5.598 |
Cg1 is the centroid of the Cd1/N11/C15/C16/N12 ring,
Cg3 that of the N12/N13/C17/N14/C16 ring,
Cg4 that of the N11/C11–C15 ring and
Cg5 that of the C18–C23 ring.
Symmetry codes: (b) -x+1, -y, -z;
(c) -x+2, -y, -z;
(d) x-1/2, -y+1/2, z+1/2. |