(Benzyl­thiol­ato-κS)phenyl­mercury(II)

Nath, P.; Bharty, M.K.; Gupta, S.K.; Butcher, R.J.; Jasinski, J.P.

doi:10.1107/S241431461700503X

metal-organic compounds

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Volume 2| Part 4| April 2017| x170503

https://doi.org/10.1107/S241431461700503X

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(Benzylthiolato-κS)phenylmercury(II)

Paras Nath,^a Manoj K. Bharty,^a ^* Sushil K. Gupta,^b Ray J. Butcher ^c and Jerry P. Jasinski ^d

^aDepartment of Chemistry, Banaras Hindu University, Varanasi 221 005, India, ^bSchool of Studies in Chemistry, Jiwaji University, Gwalior 47011, India, ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and ^dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: manoj_vns2005@yahoo.co.in

Edited by J. Simpson, University of Otago, New Zealand (Received 29 March 2017; accepted 31 March 2017; online 7 April 2017)

The title complex, [Hg(C₆H₅)(C₇H₇S)], was synthesized from benzyl 4-methylpiperidine-1-carbodithioate. In the complex, the Hg^II cation binds to a C atom of a phenyl ring and the S atom of a benzylthiolate ligand in a linear coordination geometry. The molecule is bent at the methylene C atom and the S atom, resulting in a syn conformation with respect to the benzyl and phenyl rings. The dihedral angle between the phenyl and benzyl rings is 64.6 (2)°. The crystal structure is stabilized by intermolecular Hg⋯S [3.290 (3) Å] contacts and C—H⋯π interactions, generating a three-dimensional network.

Keywords: crystal structure; phenylmercury(II)thio derivative; C—H⋯π interactions.

CCDC reference: 1509869

Structure description

Organomercury(II) cations have a high affinity for bonding through the sulfur donor sites present in amino acids, peptides and proteins (Clarkson & Magos, 2006 ; Hoffmeyer et al., 2006 ; Rooney, 2007 ). Crystal structures of several phenylmercury(II) complexes with Hg—S bonds and strong intermolecular Hg⋯S interactions have been reported (Yadav et al., 2014 ; Bharti et al., 2013 ; Nath et al., 2016 ). Mercury has long been used in medicine and industry which has caused toxicity problems. All forms of mercury are toxic in high doses (Clifton, 2007 ). Compounds with a mercapto group e.g. 2,3-dimercaptopropanol (British Anti-Lewisite) are used as antidotes in cases of mercury poisoning (Canty & Kishimoto, 1975 ). 4-Methyl-piperidinecarbodithioate forms a linear mercury(II) complex in which the dithiosulfur atom coordinates to the mercury(II) ion (Nath et al., 2016; Dar et al., 2015 ) while in the present work the benzyl ester undergoes cleavage and a sulfur atom from the benzyl mercapto moiety of the ligand coordinates to the mercury(II) cation (Fig. 1). Some complexes of the benzenemethanethiolato ligand have been reported previously (Wong et al., 2005 ; Papadopoulos et al., 1996 ; Berg et al., 1979 ). Sachs has reported many organo-mercury mercaptides, including this complex, but the crystal structure data was not reported (Sachs, 1923 ). Therefore, in this work we report the synthesis (Fig. 1), spectroscopic data and crystal structure of the title complex.

Figure 1
A reaction scheme showing the synthesis of the title compound.

The molecular structure of the title complex is shown in Fig. 2. The Hg^II cation is bound to the phenyl ipso-carbon and the thiolato sulfur atom of a benzenemethanethiolato ligand. This is generated in situ during the preparation. The geometry around Hg^II is almost linear C1—Hg—S1 = 178.0 (3)°. The phenyl rings (C1–C6 and C8–C13) are inclined to one another at a dihedral angle of 64.6 (2)°. The Hg—S1 bond length is 2.360 (2) Å which is quite similar to other reported Hg—S bonds (Bharti et al., 2013; Nath et al., 2016). The molecule is bent at the sulfur atom and methylene carbon with bond angles of 104.4 (3) and 111.4 (6)°, respectively, which is close to the regular tetrahedral angle. The Hg—S1—C7—C8 torsion angle of 2.7 (9)° reflects the fact that the benzyl and phenylmercury groups are in a syn orientation with respect to one another.

Figure 2
The molecular structure of the title compound, showing 50% probability displacement ellipsoids.

Molecules in the crystal structure are stabilized by intermolecular Hg⋯S interactions [Hg⋯S^iv 3.290 (3) Å; iv = −x + $[{3\over 2}]$ , −y + $[{3\over 2}]$ ,z + 1/2] (Fig. 3) and three C—H⋯π interactions (Fig. 4, Table 1), leading to a three-dimensional network.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 are the centroids of the benzene C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯Cg1ⁱ	0.95	3.00	3.799 (4)	143
C7—H7A⋯Cg1ⁱⁱ	0.99	2.98	3.913 (8)	157
C11—H11A⋯Cg2ⁱⁱⁱ	0.95	2.63	3.547 (6)	162
Symmetry codes: (i) -y, x, -z; (ii) $[-y+{\script{1\over 2}}, x+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 3
Crystal packing of the title compound, viewed along the b axis. Dashed lines indicate intermolecular Hg⋯S interactions.

Figure 4
A view of the packing along the c axis, showing the C—H⋯π contacts.

Synthesis and crystallization

A mixture of potassium 4-methyl-piperidinecarbodithioate (Nath et al., 2016) and benzyl chloride in absolute methanol was stirred for 3 h at room temperature. The solid benzyl 4-methylpiperidine-1-carbodithioate obtained upon removal of the solvent was washed with CCl₄ and dried. A mixture of a methanol–chloroform solution (50:50) of phenylmercury acetate 0.674 g (2 mmol) and benzyl 4-methylpiperidine-1-carbodithioate 0.531 g (2 mmol) was stirred for 2 h at at room temperature. The clear solution was filtered off and kept for crystallization, colourless prismatic crystals of the title compound suitable for X-ray analyses were obtained after 8 d (Fig. 1) Yield: 60%; m.p.: 392–394 K. Analysis found. C, 39.30; H, 3.12; S, 7.83%. Calculated for C₁₃H₁₂HgS (400.88): C, 38.94; H, 3.01; S, 8.00%. IR (selected, KBr): 3063 [ν(C—H)], 2940 [ν(C—H)], 731 [ν(C—S)] cm^{-1. 1}H NMR (CDCl₃): δ [p.p.m.] = 4.23 (s, 2H, CH₂), 7.04–7.44 (m, 10H, aromatic H). ¹³C NMR (CDCl₃): δ [p.p.m.] = 32.0 (CH₂), 127.2–146.5 (aromatic C).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Hg(C₆H₅)(C₇H₇S)]
M_r	400.88
Crystal system, space group	Tetragonal, I $[\overline{4}]$
Temperature (K)	173
a, c (Å)	20.4402 (6), 5.7266 (4)
V (Å³)	2392.6 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	13.00
Crystal size (mm)	0.60 × 0.25 × 0.22

Data collection
Diffractometer	Rigaku Xcalibur, Eos, Gemini
Absorption correction	Analytical (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.011, 0.123
No. of measured, independent and observed [I > 2σ(I)] reflections	4085, 4085, 3706
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.760

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.075, 1.04
No. of reflections	4085
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −1.26
Absolute structure	Flack x determined using 1447 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.006 (10)
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1509869

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431461700503X/sj4103sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700503X/sj4103Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(Benzylthiolato-κS)phenylmercury(II) top

Crystal data top

[Hg(C₆H₅)(C₇H₇S)]	D_x = 2.226 Mg m⁻³
M_r = 400.88	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 4836 reflections
a = 20.4402 (6) Å	θ = 3.7–32.2°
c = 5.7266 (4) Å	µ = 13.00 mm⁻¹
V = 2392.6 (2) Å³	T = 173 K
Z = 8	Prismatic, colourless
F(000) = 1488	0.60 × 0.25 × 0.22 mm

Data collection top

Rigaku Xcalibur, Eos, Gemini diffractometer	4085 independent reflections
Radiation source: fine-focus sealed X-ray tube	3706 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	R_int = 0.085
ω scans	θ_max = 32.7°, θ_min = 3.2°
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2015)	h = −29→30
T_min = 0.011, T_max = 0.123	k = −30→31
4085 measured reflections	l = −8→8

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0241P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.075	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.96 e Å⁻³
4085 reflections	Δρ_min = −1.26 e Å⁻³
136 parameters	Absolute structure: Flack x determined using 1447 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.006 (10)

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
Hg	0.67354 (2)	0.75027 (2)	0.68688 (6)	0.02102 (8)
S1	0.77105 (10)	0.81205 (10)	0.6783 (5)	0.0240 (4)
C1	0.5873 (4)	0.6967 (4)	0.6822 (19)	0.0208 (16)
C2	0.5709 (4)	0.6553 (5)	0.8683 (17)	0.026 (2)
H2A	0.5983	0.6536	1.0021	0.031*
C3	0.5150 (4)	0.6166 (5)	0.8591 (18)	0.029 (2)
H3A	0.5047	0.5879	0.9846	0.035*
C4	0.4742 (4)	0.6201 (4)	0.6637 (19)	0.0277 (19)
H4A	0.4357	0.5941	0.6564	0.033*
C5	0.4895 (5)	0.6608 (5)	0.4846 (19)	0.033 (2)
H5A	0.4614	0.6629	0.3525	0.040*
C6	0.5460 (5)	0.6999 (5)	0.4901 (18)	0.030 (2)
H6A	0.5558	0.7283	0.3635	0.036*
C7	0.7490 (4)	0.8871 (5)	0.516 (2)	0.035 (3)
H7A	0.7590	0.9258	0.6136	0.042*
H7B	0.7758	0.8899	0.3724	0.042*
C8	0.6781 (4)	0.8876 (4)	0.4522 (19)	0.0234 (18)
C9	0.6320 (5)	0.9142 (4)	0.6053 (18)	0.026 (2)
H9A	0.6462	0.9349	0.7449	0.031*
C10	0.5666 (5)	0.9108 (5)	0.556 (2)	0.034 (2)
H10A	0.5359	0.9278	0.6652	0.041*
C11	0.5444 (5)	0.8833 (5)	0.351 (2)	0.035 (3)
H11A	0.4988	0.8813	0.3191	0.042*
C12	0.5890 (5)	0.8585 (5)	0.194 (2)	0.033 (2)
H12A	0.5741	0.8399	0.0514	0.039*
C13	0.6563 (5)	0.8609 (5)	0.2429 (16)	0.027 (2)
H13A	0.6869	0.8442	0.1332	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg	0.01884 (15)	0.02023 (16)	0.02399 (15)	−0.00296 (12)	0.00159 (14)	0.00177 (14)
S1	0.0174 (9)	0.0257 (10)	0.0288 (11)	−0.0027 (7)	−0.0027 (10)	0.0064 (11)
C1	0.021 (4)	0.014 (3)	0.028 (4)	−0.003 (3)	−0.001 (4)	−0.004 (4)
C2	0.018 (4)	0.034 (5)	0.026 (5)	0.002 (3)	−0.001 (3)	0.003 (4)
C3	0.017 (4)	0.032 (5)	0.038 (6)	−0.005 (3)	0.004 (4)	0.010 (4)
C4	0.022 (4)	0.029 (4)	0.033 (5)	−0.005 (3)	0.003 (4)	−0.006 (4)
C5	0.029 (5)	0.036 (5)	0.034 (6)	−0.002 (4)	−0.016 (4)	−0.002 (4)
C6	0.032 (5)	0.031 (5)	0.026 (5)	−0.004 (4)	−0.007 (4)	0.005 (4)
C7	0.018 (4)	0.030 (5)	0.058 (8)	−0.005 (3)	−0.003 (5)	0.015 (5)
C8	0.027 (4)	0.014 (4)	0.030 (5)	−0.005 (3)	0.002 (4)	0.003 (4)
C9	0.030 (5)	0.020 (4)	0.027 (5)	−0.001 (3)	−0.001 (4)	−0.003 (4)
C10	0.030 (5)	0.029 (5)	0.044 (6)	0.003 (4)	0.009 (5)	−0.001 (5)
C11	0.029 (5)	0.028 (5)	0.048 (7)	−0.002 (4)	−0.011 (5)	0.011 (5)
C12	0.044 (6)	0.027 (4)	0.027 (5)	−0.005 (4)	−0.009 (6)	0.000 (5)
C13	0.036 (5)	0.027 (4)	0.018 (5)	0.004 (4)	0.008 (4)	0.003 (3)

Geometric parameters (Å, º) top

Hg—C1	2.076 (8)	C7—C8	1.496 (12)
Hg—S1	2.360 (2)	C7—H7A	0.9900
S1—C7	1.848 (10)	C7—H7B	0.9900
C1—C6	1.388 (13)	C8—C13	1.390 (13)
C1—C2	1.402 (13)	C8—C9	1.398 (13)
C2—C3	1.390 (12)	C9—C10	1.368 (13)
C2—H2A	0.9500	C9—H9A	0.9500
C3—C4	1.398 (14)	C10—C11	1.378 (16)
C3—H3A	0.9500	C10—H10A	0.9500
C4—C5	1.357 (14)	C11—C12	1.378 (16)
C4—H4A	0.9500	C11—H11A	0.9500
C5—C6	1.404 (13)	C12—C13	1.406 (14)
C5—H5A	0.9500	C12—H12A	0.9500
C6—H6A	0.9500	C13—H13A	0.9500

C1—Hg—S1	178.0 (3)	S1—C7—H7A	109.4
C7—S1—Hg	104.4 (3)	C8—C7—H7B	109.4
C6—C1—C2	119.0 (7)	S1—C7—H7B	109.4
C6—C1—Hg	120.2 (7)	H7A—C7—H7B	108.0
C2—C1—Hg	120.8 (7)	C13—C8—C9	118.5 (8)
C3—C2—C1	120.7 (8)	C13—C8—C7	121.3 (9)
C3—C2—H2A	119.6	C9—C8—C7	120.2 (10)
C1—C2—H2A	119.6	C10—C9—C8	120.7 (9)
C2—C3—C4	119.4 (9)	C10—C9—H9A	119.7
C2—C3—H3A	120.3	C8—C9—H9A	119.7
C4—C3—H3A	120.3	C9—C10—C11	121.2 (10)
C5—C4—C3	119.9 (8)	C9—C10—H10A	119.4
C5—C4—H4A	120.0	C11—C10—H10A	119.4
C3—C4—H4A	120.0	C12—C11—C10	119.3 (9)
C4—C5—C6	121.4 (9)	C12—C11—H11A	120.4
C4—C5—H5A	119.3	C10—C11—H11A	120.4
C6—C5—H5A	119.3	C11—C12—C13	120.3 (10)
C1—C6—C5	119.4 (9)	C11—C12—H12A	119.9
C1—C6—H6A	120.3	C13—C12—H12A	119.9
C5—C6—H6A	120.3	C8—C13—C12	119.9 (9)
C8—C7—S1	111.4 (6)	C8—C13—H13A	120.0
C8—C7—H7A	109.4	C12—C13—H13A	120.0

C6—C1—C2—C3	1.6 (14)	S1—C7—C8—C9	89.2 (10)
Hg—C1—C2—C3	−176.3 (7)	C13—C8—C9—C10	3.6 (14)
C1—C2—C3—C4	−1.2 (14)	C7—C8—C9—C10	−175.4 (9)
C2—C3—C4—C5	0.4 (14)	C8—C9—C10—C11	−2.3 (15)
C3—C4—C5—C6	0.0 (16)	C9—C10—C11—C12	0.2 (15)
C2—C1—C6—C5	−1.1 (14)	C10—C11—C12—C13	0.7 (15)
Hg—C1—C6—C5	176.7 (8)	C9—C8—C13—C12	−2.7 (13)
C4—C5—C6—C1	0.4 (16)	C7—C8—C13—C12	176.2 (9)
Hg—S1—C7—C8	2.7 (9)	C11—C12—C13—C8	0.6 (14)
S1—C7—C8—C13	−89.7 (11)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 are the centroids of the benzene C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Cg1ⁱ	0.95	3.00	3.799 (4)	143
C7—H7A···Cg1ⁱⁱ	0.99	2.98	3.913 (8)	157
C11—H11A···Cg2ⁱⁱⁱ	0.95	2.63	3.547 (6)	162

Symmetry codes: (i) −y, x, −z; (ii) −y+1/2, x+1/2, −z+1/2; (iii) −x−1/2, −y+1/2, z−1/2.

Acknowledgements

MKB thanks the Science and Engineering Research Board, India for the award of a Project (No. SB/EMEQ-150/2014). JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Benzyl­thiol­ato-κS)phenyl­mercury(II)

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

metal-organic compounds

(Benzylthiolato-κS)phenylmercury(II)