Design and synthesis of methyl 2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}­acetate (phpy2NS) as a ligand for complexes of Group 12 elements: structural assessment and hydrogen-bonded supra­molecular assembly analysis

Castiñeiras, A.; García-Santos, I.; Saa, M.

doi:10.1107/S205322961900682X

Design and synthesis of methyl 2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate (phpy2NS) as a ligand for complexes of Group 12 elements: structural assessment and hydrogen-bonded supramolecular assembly analysis

A. Castiñeiras, I. García-Santos and M. Saa

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), [Zn_0.76Cd_0.24(C₁₆H₁₄N₄O₂S)₂(CH₃OH)₂][Cd₂Br₆] or [Zn_0.76Cd_0.24(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 Zn^II and 24% of Cd^II. 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.

Keywords: 1,2,3-triazole; metal complex; crystal structure; supramolecular architecture; hydrogen bonding; noncovalent interactions; stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961900682X/lg3239sup1.cif Contains datablocks Compound_1, Compound_2, Compound_3, Compound_4, global
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961900682X/lg3239Compound_1sup2.hkl Contains datablock Compound_1
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961900682X/lg3239Compound_2sup3.hkl Contains datablock Compound_2
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961900682X/lg3239Compound_3sup4.hkl Contains datablock Compound_3
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961900682X/lg3239Compound_4sup5.hkl Contains datablock Compound_4
	Portable Document Format (PDF) file https://doi.org/10.1107/S205322961900682X/lg3239sup6.pdf X-ray fluorescence spectrum, ICP-MS calibration curves, NMR spectra and supramolecular diagrams

CCDC references: 1837084; 1915706; 1837083; 1849847

Computing details top

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-3H-1,2,4-triazole-3-thione (Compound_1) top

Crystal data top

C₁₃H₁₀N₄S	F(000) = 1056
M_r = 254.31	D_x = 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	R_int = 0.040
ω and phi scans	θ_max = 26.4°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −35→34
T_min = 0.856, T_max = 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(F_o²) + (0.0424P)² + 1.0135P] where P = (F_o² + 2F_c²)/3
4845 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −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	U_iso*/U_eq
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)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate (Compound_2) top

Crystal data top

C₁₆H₁₄N₄O₂S	F(000) = 680
M_r = 326.37	D_x = 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	R_int = 0.048
ω and phi scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −7→7
T_min = 0.877, T_max = 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(F_o²) + (0.0397P)² + 0.9896P] where P = (F_o² + 2F_c²)/3
3477 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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-κ²N¹,N⁵]sulfanyl}acetato)zinc(II)/cadmium(II) hexabromidocadmiate(II) (Compound_3) top

Crystal data top

[Zn_0.76Cd_0.24(C₁₆H₁₄N₄O₂S)₂(CH₄O)₂][Cd₂Br₆]	F(000) = 1433
M_r = 1497.85	D_x = 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	R_int = 0.079
φ or ω oscillation scans	θ_max = 29.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −15→15
T_min = 0.489, T_max = 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(F_o²) + (0.0251P)²] where P = (F_o² + 2F_c²)/3
6660 reflections	(Δ/σ)_max = 0.001
269 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.94 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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···Br1^iv	0.98	3.03	3.668 (5)	124
C10—H10A···Br3^v	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···Br2^vi	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-κ²N¹,N⁵]sulfanyl}acetato)mercury(II) (Compound_4) top

Crystal data top

[HgCl₂(C₁₆H₁₄N₄O₂S)]	Z = 2
M_r = 597.86	F(000) = 568
Triclinic, P1	D_x = 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	R_int = 0.052
ω and phi scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan SADABS	h = −10→10
T_min = 0.656, T_max = 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(F_o²) + (0.0212P)² + 3.2485P] where P = (F_o² + 2F_c²)/3
3765 reflections	(Δ/σ)_max = 0.002
236 parameters	Δρ_max = 1.83 e Å⁻³
0 restraints	Δρ_min = −1.15 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 top

The 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···S1A^a	0.90	2.38	3.265 (2)	168.4	-x, -y, -z+1
	N3B—H30B···S1B^b	0.83	2.47	3.285 (2)	166.6	-x+1, -y, -z+1
	C9A—H9A···S1A^c	0.95	2.93	3.852 (2)	163.1	x, y+1, z
	C9B—H9B···S1B^c	0.95	2.81	3.738 (2)	166.8	x,y+1,z

2	C11—H11···S1^a	0.95	2.99	3.757 (2)	138.4	x+1, -y+1/2, z+1/2
	C11—H11···O2^a	0.95	2.48	3.399 (2)	162.5	x+1, -y+1/2, z+1/2
	C19—H19···N11^b	0.95	2.62	3.538 (3)	162.0	x-1, y, z
	C113—H113···S1^c	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···Br3^c	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···Br1^d	0.98	3.03	3.884 (5)	124.2	x-1/2, -y+1/2, z-1/2
	C10—H10A···Br3^e	0.98	2.91	3.750 (5)	144.6	-x+1/2, y-1/2, -z+1/2
	C11—H11···O12^a	0.95	2.53	3.296 (5)	137.6	-x+1, -y, -z
	C11—H11···N13^a	0.95	2.61	3.431 (6)	145.3	-x+1, -y, -z
	C12—H12···Br2^f	0.95	2.98	3.636 (4)	127.2	-x+3/2, y-1/2, -z+1/2

4	C3—H3C···Cl2^a	0.98	2.79	3.583 (8)	138.2	x-1, y, z
	C19—H19···O1^b	0.95	2.59	3.172 (6)	119.9	x+1, y, z
	C113—H113···Cl2^c	0.95	2.84	3.551 (6)	132.3	x-1, y-1, z

Intermolecular interaction parameters (Å, °) for compound 1 top

X—Y···π interactions	Y···Cg	γ	X—Y···Cg	X···Cg'
C113—H113···Cg2^d	2.69	11.35	151	3.555
C213—H213···Cg5^d	2.82	10.40	150	3.670
C17—S1···Cg2^e	3.66	12.04	163	5.298
C27—S2···Cg5^e	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 top

X—H···π interactions	H···Cg	γ	X—H···Cg	X···Cg'
C12—H12···Cg3^a	2.76	8.47	143	3.562
C19—H19···Cg2^b	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 top

3				4
M1*—N12	2.092 (3)	N12—M1—N12^a	180.0	Hg1—Cl1	2.3483 (12)	Cl1—Hg1—Cl2	148.93 (5)
M1—N12^a	2.092 (3)	N12—M1—N11^a	102.85 (12)	Hg1—Cl2	2.3579 (14)	Cl1—Hg1—N11	103.23 (10)
M1—N11^a	2.141 (3)	N12^a—M1—N11^a	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—O10^a	2.284 (3)	N12^a—M1—N11	102.85(12			Cl2—Hg1—N12	86.27 (10)
M1—O10	2.284 (3)	N11^a—M1—N11	180.0			N11—Hg1—N12	67.54 (14)
Cd2—Br3	2.5157 (5)	N12—M1—O10^a	90.97 (11)
Cd2—Br2	2.5699 (5)	N12^a—M1—O10^a	89.03 (11)
Cd2—Br1^b	2.6461 (5)	N11^a—M1—O10^a	90.66 (11)
Cd2—Br1	2.6508 (5)	N11—M1—O10^a	89.34 (11)
Br1—Cd2^b	2.6461 (5)	N12—M1—O10	89.03 (11)
M1—Cd2	6.3389 (4)	N12^a—M1—O10	90.97 (11)
Cd2—Cd2^b	3.5698 (5)	N11a—M1—O10	89.34 (11)
Br1—Br1^b	3.9132 (8)	N11—M1—O10	90.66 (11)
		O10^a—M1—O10	180.0
		Br3—Cd2—Br2	113.643 (16)
		Br3—Cd2—Br1^b	117.563 (18)
		Br2—Cd2—Br1^b	106.577 (15)
		Br3—Cd2—Br1	116.462 (16)
		Br2—Cd2—Br1	105.201 (17)
		Br1^b—Cd2—Br1	95.255 (14)
		Cd2^b—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 top

X—Y···π interactions	Y···Cg	γ	X—Y···Cg	X···Cg'
C14—H14···Cg5	2.93	28.66	149	3.774
C22—H22···Cg4^c	2.85	8.62	151	3.710
Cd2—Br2···Cg1	3.629	24.21	144.79	5.919
Cd2—Br2···Cg1^b	3.629	24.21	144.79	5.919
Cd2—Br2···Cg3	3.496	17.17	143.81	5.775
Cd2—Br3···Cg3^d	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.

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Design and synthesis of methyl 2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}­acetate (phpy2NS) as a ligand for complexes of Group 12 elements: structural assessment and hydrogen-bonded supra­molecular assembly analysis

Supporting information

Design and synthesis of methyl 2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate (phpy2NS) as a ligand for complexes of Group 12 elements: structural assessment and hydrogen-bonded supramolecular assembly analysis