catena-Poly[bis­(dibenzyl­ammonium) [[dichloridomercurate(II)]-μ-sulfato-κ2O:O′]]

Boye, M.S.; Diasse-Sarr, A.; Grosjean, A.; Guionneau, P.

doi:10.1107/S1600536812006927

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m340

doi:10.1107/S1600536812006927

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catena-Poly[bis(dibenzylammonium) [[dichloridomercurate(II)]-μ-sulfato-κ²O:O′]]

Mouhamadou Sembene Boye,^a ^* Aminata Diasse-Sarr,^a Arnaud Grosjean ^b and Philippe Guionneau ^b

^aDépartement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bCNRS, Université de Bordeaux, ICMCB, 87 Avenue du Docteur A. Schweitzer, F-33608 Pessac, France
^*Correspondence e-mail: mouhasboye@hotmail.com

(Received 5 January 2012; accepted 15 February 2012; online 29 February 2012)

The structure of the title compound, (C₁₄H₁₆N)₂[HgCl₂(SO₄)], consists of an infinite chain propagating along the c direction, containing Hg^II ions tetracoordinated by two bridging O atoms of bis-monodentate sulfate anions and two chloride ligands. In the the crystal, N—H⋯O hydrogen bonding between the cations and the anionic chains consolidates the packing. The crystal structure was determined from an inversion twin with approximately equal twin domains.

Related literature

For the behavior of sulfate as a ligand, see: Sall et al. (1992 ); Diop et al. (2000 ); Boye et al. (2007 ). For the IR vibrational frequencies of sulfate, see: Nakamoto (1978 ).

Experimental

Crystal data

(C₁₄H₁₆N)₂[HgCl₂(SO₄)]
M_r = 764.14
Monoclinic, C c
a = 22.8275 (5) Å
b = 12.9547 (3) Å
c = 10.1512 (3) Å
β = 92.095 (2)°
V = 2999.94 (13) Å³
Z = 4
Mo Kα radiation
μ = 5.41 mm⁻¹
T = 293 K
0.40 × 0.25 × 0.25 mm

Data collection

Nonius Kappa CCD diffractometer
Absorption correction: empirical (using intensity measurements) (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.221, T_max = 0.345
9151 measured reflections
5464 independent reflections
5304 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 1.02
5464 reflections
315 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.12 e Å⁻³
Δρ_min = −2.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.90	2.44	2.920 (9)	114
N1—H1A⋯O3ⁱ	0.90	2.29	3.037 (10)	141
N1—H1B⋯O3ⁱⁱ	0.90	1.90	2.766 (9)	161
N2—H2C⋯O4ⁱⁱⁱ	0.90	2.32	3.043 (10)	137
N2—H2C⋯O1ⁱⁱⁱ	0.90	2.12	2.857 (9)	139
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2003 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812006927/fi2124sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006927/fi2124Isup2.hkl

checkCIF report

Comment top

In the framework of our research work for understanding the behavior of sulfate acting as ligand (Sall et al., 1992; Diop et al., 2000; Boye et al., 2007), we report the crystallographic study of 2[(C₆H₅CH₂)₂NH₂]⁺[HgSO₄Cl₂]^2-.

The structure obtained by single-crystal XRD (Fig. 1) indicate an infinite chain in which each Hg atom is tetracoordinated by two O atoms of two sulfates and two chloride atoms in a distorted tetrahedral geometry. The tetrahedral angles are in the range 80.8 (2)–152.42 (10). The sulfate behaves as a bidentate anion with disparate Hg—O distances [Hg—O(1) = 2.433 (6) and Hg—O(4) = 2.533 (7) Å]. The S—O distances vary from 1.446 (6) to 1.492 (7) Å, the S—O distances for two O atoms linked to Hg atoms [1.474 (7)–1.492 (5) Å] are longer than those non-bonding [1.446 (6)–1.465 (6) Å].

The behavior of bidentate sulfate (C_2v symmetry) is confirmed by the infrared data, ν_s(SO₄^2-) appears at 988 cm^-1 (Nakamoto, 1978) and ν_as(SO₄^2-) splits into three bands (1115, 1082, 1041 cm^-1). The crystal packing of the title compound is shown in Fig.2.

Related literature top

For the behavior of sulfate as a ligand, see: Sall et al. (1992); Diop et al. (2000); Boye et al. (2007). For the IR vibrational frequencies of sulfate, see: Nakamoto (1978).

Experimental top

(C₆H₅CH₂)₂NH, H₂SO₄ and HgCl₂ (Aldrich chemicals) were used without further purification.

The title compound was obtained by mixing ethanolic solutions of (C₆H₅CH₂)₂NH (17.66 mmol), H₂SO₄ (8.83 mmol) and HgCl₂ (4.41 mmol) in a 8–4–1 ratio. The mixture was stirred for around two hours at room temperature. Suitable crystals for X-ray diffraction were obtained after slow solvent evaporation. (m.p. 459 K).

The title compound was isolated according to the following reaction:

2(C₆H₅CH₂)₂NH + H₂SO₄ + HgCl₂ → 2[(C₆H₅CH₂)₂NH₂]⁺ [HgSO₄Cl₂]^2-

- Infrared data (cm^-1) [vs = very strong; s = strong]

988 s ν_s(SO₄^2-); 1115 s, 1082 s, 1041 s ν_as(SO₄^2-); 454 s δ_s(SO₄^2-); 610 vs δ_as(SO₄^2-).

Computing details top

Data collection: COLLECT (Nonius, 2003); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing viewed along the c axis. H atoms have been omitted for clarity.
	Fig. 3. Chains propagate along the c direction. H atoms have been omitted for clarity.

catena-Poly[bis(dibenzylammonium) [[dichloridomercurate(II)]-µ-sulfato-κ²O:O']] top

Crystal data top

(C₁₄H₁₆N)₂[HgCl₂(SO₄)]	F(000) = 1504
M_r = 764.14	D_x = 1.692 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C-2yc	Cell parameters from 10249 reflections
a = 22.8275 (5) Å	θ = 0.4–26.0°
b = 12.9547 (3) Å	µ = 5.41 mm⁻¹
c = 10.1512 (3) Å	T = 293 K
β = 92.095 (2)°	Prism, colourless
V = 2999.94 (13) Å³	0.40 × 0.25 × 0.25 mm
Z = 4

Data collection top

Nonius Kappa CCD diffractometer	5464 independent reflections
Radiation source: fine-focus sealed tube	5304 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.7°
Absorption correction: empirical (using intensity measurements) (SCALEPACK; Otwinowski & Minor, 1997)	h = −27→28
T_min = 0.221, T_max = 0.345	k = −15→15
9151 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.099P)² + 6.3836P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.005
5464 reflections	Δρ_max = 1.12 e Å⁻³
315 parameters	Δρ_min = −2.40 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (3)

Crystal data top

(C₁₄H₁₆N)₂[HgCl₂(SO₄)]	V = 2999.94 (13) Å³
M_r = 764.14	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 22.8275 (5) Å	µ = 5.41 mm⁻¹
b = 12.9547 (3) Å	T = 293 K
c = 10.1512 (3) Å	0.40 × 0.25 × 0.25 mm
β = 92.095 (2)°

Data collection top

Nonius Kappa CCD diffractometer	5464 independent reflections
Absorption correction: empirical (using intensity measurements) (SCALEPACK; Otwinowski & Minor, 1997)	5304 reflections with I > 2σ(I)
T_min = 0.221, T_max = 0.345	R_int = 0.020
9151 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	2 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	Δρ_max = 1.12 e Å⁻³
5464 reflections	Δρ_min = −2.40 e Å⁻³
315 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	0.47859 (7)	0.47550 (14)	0.25406 (15)	0.0294 (3)
O1	0.4797 (2)	0.4792 (5)	0.1074 (4)	0.0377 (11)
O3	0.4174 (2)	0.4818 (5)	0.2924 (6)	0.0427 (12)
O2	0.5059 (3)	0.3804 (5)	0.2988 (6)	0.0460 (13)
N1	0.8594 (3)	−0.0322 (6)	0.5261 (7)	0.0454 (15)
H1A	0.8729	0.0132	0.5870	0.054*
H1B	0.8851	−0.0336	0.4610	0.054*
C2	0.8012 (4)	0.0059 (8)	0.4703 (8)	0.0452 (18)
H2A	0.7860	−0.0443	0.4070	0.054*
H2B	0.8076	0.0698	0.4231	0.054*
C4	0.7555 (4)	0.0246 (7)	0.5720 (8)	0.0428 (17)
C6	0.7115 (5)	−0.0450 (9)	0.5881 (11)	0.057 (2)
H6	0.7110	−0.1064	0.5406	0.068*
C5	0.7568 (5)	0.1163 (8)	0.6417 (9)	0.051 (2)
H5	0.7867	0.1639	0.6307	0.061*
C7	0.7123 (5)	0.1359 (8)	0.7291 (11)	0.057 (2)
H7	0.7122	0.1980	0.7750	0.068*
C8	0.6683 (5)	0.0643 (9)	0.7486 (12)	0.063 (3)
H8	0.6400	0.0764	0.8102	0.075*
C11	0.5329 (10)	0.1734 (10)	0.580 (2)	0.0868 (16)
C17	0.6597 (4)	0.4041 (7)	0.4804 (10)	0.0476 (19)
C16	0.6563 (4)	0.3853 (10)	0.3472 (10)	0.059 (3)
H16	0.6204	0.3923	0.3015	0.071*
C13	0.7640 (4)	0.3654 (9)	0.4791 (12)	0.055 (2)
H13	0.8000	0.3616	0.5244	0.067*
C14	0.7590 (5)	0.3438 (12)	0.3478 (13)	0.067 (3)
H14	0.7915	0.3210	0.3035	0.081*
C15	0.7054 (5)	0.3559 (16)	0.2797 (13)	0.086 (4)
H15	0.7024	0.3443	0.1892	0.103*
C12	0.7138 (4)	0.3934 (8)	0.5433 (10)	0.050 (2)
H12	0.7168	0.4055	0.6336	0.060*
C18	0.6675 (5)	−0.0243 (10)	0.6755 (13)	0.067 (3)
H18	0.6371	−0.0713	0.6843	0.081*
C29	0.8848 (4)	−0.2461 (7)	0.3960 (9)	0.0486 (19)
H29	0.9186	−0.2067	0.3883	0.058*
C30	0.8736 (8)	−0.3307 (8)	0.3096 (13)	0.069 (4)
H30	0.9000	−0.3463	0.2449	0.083*
C31	0.8241 (7)	−0.3898 (10)	0.3207 (14)	0.074 (3)
H31	0.8170	−0.4461	0.2656	0.088*
C33	0.7948 (5)	−0.2806 (11)	0.4996 (12)	0.064 (3)
H33	0.7671	−0.2645	0.5613	0.076*
C32	0.7861 (6)	−0.3641 (9)	0.4130 (17)	0.078 (4)
H32	0.7524	−0.4037	0.4201	0.094*
C34	0.8456 (4)	−0.2227 (7)	0.4910 (7)	0.0407 (16)
C35	0.8576 (5)	−0.1388 (8)	0.5890 (9)	0.051 (2)
H35A	0.8949	−0.1522	0.6348	0.061*
H35B	0.8274	−0.1397	0.6538	0.061*
N2	0.5594 (3)	0.3587 (6)	0.5478 (7)	0.0403 (14)
H2C	0.5291	0.3831	0.5927	0.048*
H2D	0.5470	0.3490	0.4636	0.048*
C37	0.6092 (4)	0.4390 (7)	0.5523 (10)	0.0467 (19)
H37A	0.5948	0.5033	0.5144	0.056*
H37B	0.6212	0.4521	0.6434	0.056*
C40	0.4857 (9)	0.1670 (12)	0.6625 (18)	0.0868 (16)
H40	0.4829	0.2140	0.7312	0.104*
C42	0.5402 (8)	0.1009 (11)	0.4852 (15)	0.0868 (16)
H42	0.5723	0.1030	0.4312	0.104*
C38	0.4515 (8)	0.0193 (11)	0.5571 (16)	0.0868 (16)
H38	0.4247	−0.0347	0.5558	0.104*
C39	0.4449 (8)	0.0952 (12)	0.6454 (15)	0.0868 (16)
H39	0.4114	0.0973	0.6948	0.104*
C41	0.4946 (8)	0.0166 (11)	0.4705 (14)	0.0868 (16)
H41	0.4963	−0.0340	0.4057	0.104*
O4	0.5118 (3)	0.5651 (6)	0.3063 (7)	0.0540 (17)
C3	0.5785 (5)	0.2590 (8)	0.6051 (10)	0.052 (2)
H3A	0.5854	0.2670	0.6993	0.063*
H3B	0.6152	0.2387	0.5673	0.063*
Cl1	0.40170 (12)	0.2706 (3)	−0.0297 (3)	0.0596 (7)
Cl2	0.59979 (13)	0.2769 (3)	0.0059 (4)	0.0672 (8)
Hg1	0.50000 (3)	0.315360 (17)	0.00102 (5)	0.04119 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0266 (7)	0.0391 (8)	0.0226 (7)	−0.0018 (6)	0.0036 (6)	0.0009 (6)
O1	0.041 (3)	0.054 (3)	0.018 (2)	−0.003 (2)	0.0051 (19)	−0.002 (2)
O3	0.033 (3)	0.055 (3)	0.041 (3)	−0.003 (2)	0.011 (2)	0.005 (2)
O2	0.048 (3)	0.042 (3)	0.048 (3)	0.001 (2)	−0.001 (2)	0.009 (2)
N1	0.045 (4)	0.054 (4)	0.036 (3)	−0.011 (3)	0.000 (3)	−0.004 (3)
C2	0.040 (4)	0.059 (5)	0.036 (4)	−0.006 (4)	0.001 (3)	−0.001 (4)
C4	0.044 (4)	0.052 (5)	0.032 (3)	−0.001 (3)	−0.006 (3)	0.005 (3)
C6	0.048 (5)	0.066 (6)	0.057 (5)	−0.016 (4)	0.005 (4)	−0.009 (5)
C5	0.059 (5)	0.048 (5)	0.045 (4)	0.001 (4)	−0.010 (4)	0.003 (4)
C7	0.057 (5)	0.056 (5)	0.056 (5)	0.025 (4)	−0.007 (4)	−0.009 (4)
C8	0.052 (5)	0.075 (7)	0.061 (6)	0.012 (5)	−0.002 (4)	0.004 (5)
C11	0.109 (5)	0.068 (3)	0.082 (4)	−0.007 (3)	−0.009 (3)	0.008 (3)
C17	0.044 (4)	0.046 (5)	0.053 (5)	0.007 (4)	0.010 (4)	0.007 (4)
C16	0.036 (4)	0.093 (8)	0.048 (5)	0.013 (4)	−0.004 (4)	0.010 (5)
C13	0.039 (4)	0.063 (6)	0.064 (6)	0.007 (4)	0.002 (4)	−0.002 (5)
C14	0.041 (5)	0.098 (8)	0.065 (7)	0.015 (5)	0.018 (5)	−0.004 (6)
C15	0.043 (5)	0.162 (13)	0.053 (6)	0.023 (7)	0.012 (5)	−0.015 (8)
C12	0.038 (4)	0.058 (5)	0.052 (5)	0.002 (4)	−0.003 (4)	0.004 (4)
C18	0.049 (5)	0.070 (7)	0.084 (8)	0.000 (5)	0.023 (5)	−0.013 (6)
C29	0.055 (5)	0.038 (4)	0.054 (5)	−0.007 (4)	0.013 (4)	0.003 (3)
C30	0.116 (11)	0.040 (5)	0.051 (6)	0.003 (6)	0.010 (6)	0.001 (4)
C31	0.094 (9)	0.056 (6)	0.069 (7)	−0.008 (6)	−0.017 (7)	−0.006 (6)
C33	0.063 (6)	0.069 (7)	0.060 (6)	−0.018 (5)	0.016 (5)	0.013 (6)
C32	0.067 (7)	0.045 (6)	0.121 (12)	−0.028 (5)	−0.010 (7)	0.006 (7)
C34	0.048 (4)	0.042 (4)	0.032 (4)	−0.011 (3)	−0.002 (3)	0.004 (3)
C35	0.065 (6)	0.054 (5)	0.033 (4)	−0.006 (4)	−0.006 (4)	−0.006 (4)
N2	0.032 (3)	0.047 (4)	0.042 (4)	0.006 (3)	0.009 (3)	0.001 (3)
C37	0.042 (4)	0.041 (4)	0.058 (5)	0.009 (3)	0.004 (4)	0.000 (4)
C40	0.109 (5)	0.068 (3)	0.082 (4)	−0.007 (3)	−0.009 (3)	0.008 (3)
C42	0.109 (5)	0.068 (3)	0.082 (4)	−0.007 (3)	−0.009 (3)	0.008 (3)
C38	0.109 (5)	0.068 (3)	0.082 (4)	−0.007 (3)	−0.009 (3)	0.008 (3)
C39	0.109 (5)	0.068 (3)	0.082 (4)	−0.007 (3)	−0.009 (3)	0.008 (3)
C41	0.109 (5)	0.068 (3)	0.082 (4)	−0.007 (3)	−0.009 (3)	0.008 (3)
O4	0.046 (3)	0.078 (5)	0.038 (3)	−0.025 (3)	0.016 (3)	−0.022 (3)
C3	0.048 (5)	0.054 (5)	0.054 (5)	−0.002 (4)	−0.008 (4)	0.016 (4)
Cl1	0.0447 (13)	0.0551 (16)	0.0792 (18)	−0.0145 (12)	0.0057 (12)	0.0028 (13)
Cl2	0.0498 (15)	0.075 (2)	0.0761 (19)	0.0215 (15)	−0.0071 (13)	−0.0090 (16)
Hg1	0.04012 (18)	0.04296 (19)	0.04054 (18)	0.00013 (15)	0.00241 (10)	−0.00068 (16)

Geometric parameters (Å, º) top

S1—O2	1.446 (6)	C18—H18	0.9300
S1—O3	1.465 (5)	C29—C34	1.374 (13)
S1—O4	1.473 (7)	C29—C30	1.422 (15)
S1—O1	1.491 (5)	C29—H29	0.9300
O1—Hg1	2.433 (6)	C30—C31	1.37 (2)
N1—C2	1.508 (12)	C30—H30	0.9300
N1—C35	1.523 (12)	C31—C32	1.34 (2)
N1—H1A	0.9000	C31—H31	0.9300
N1—H1B	0.9000	C33—C34	1.386 (13)
C2—C4	1.514 (12)	C33—C32	1.40 (2)
C2—H2A	0.9700	C33—H33	0.9300
C2—H2B	0.9700	C32—H32	0.9300
C4—C6	1.364 (13)	C34—C35	1.492 (12)
C4—C5	1.382 (13)	C35—H35A	0.9700
C6—C18	1.390 (14)	C35—H35B	0.9700
C6—H6	0.9300	N2—C3	1.477 (12)
C5—C7	1.396 (14)	N2—C37	1.539 (11)
C5—H5	0.9300	N2—H2C	0.9000
C7—C8	1.385 (17)	N2—H2D	0.9000
C7—H7	0.9300	C37—H37A	0.9700
C8—C18	1.367 (17)	C37—H37B	0.9700
C8—H8	0.9300	C40—C39	1.32 (2)
C11—C42	1.36 (2)	C40—H40	0.9300
C11—C40	1.39 (3)	C42—C41	1.51 (2)
C11—C3	1.536 (19)	C42—H42	0.9300
C17—C16	1.374 (15)	C38—C41	1.34 (2)
C17—C12	1.375 (13)	C38—C39	1.34 (2)
C17—C37	1.459 (12)	C38—H38	0.9300
C16—C15	1.388 (14)	C39—H39	0.9300
C16—H16	0.9300	C41—H41	0.9300
C13—C14	1.363 (18)	O4—Hg1ⁱ	2.533 (7)
C13—C12	1.387 (14)	C3—H3A	0.9700
C13—H13	0.9300	C3—H3B	0.9700
C14—C15	1.392 (18)	Cl1—Hg1	2.327 (3)
C14—H14	0.9300	Cl2—Hg1	2.331 (3)
C15—H15	0.9300	Hg1—O4ⁱⁱ	2.533 (7)
C12—H12	0.9300

O2—S1—O3	111.6 (4)	C31—C30—C29	120.6 (13)
O2—S1—O4	110.3 (4)	C31—C30—H30	119.7
O3—S1—O4	110.0 (4)	C29—C30—H30	119.7
O2—S1—O1	108.5 (4)	C32—C31—C30	118.3 (12)
O3—S1—O1	108.3 (3)	C32—C31—H31	120.8
O4—S1—O1	107.9 (4)	C30—C31—H31	120.8
S1—O1—Hg1	115.2 (3)	C34—C33—C32	118.5 (11)
C2—N1—C35	114.7 (7)	C34—C33—H33	120.7
C2—N1—H1A	108.6	C32—C33—H33	120.7
C35—N1—H1A	108.6	C31—C32—C33	123.2 (11)
C2—N1—H1B	108.6	C31—C32—H32	118.4
C35—N1—H1B	108.6	C33—C32—H32	118.4
H1A—N1—H1B	107.6	C29—C34—C33	119.5 (9)
N1—C2—C4	114.5 (7)	C29—C34—C35	121.3 (8)
N1—C2—H2A	108.6	C33—C34—C35	119.1 (9)
C4—C2—H2A	108.6	C34—C35—N1	112.8 (7)
N1—C2—H2B	108.6	C34—C35—H35A	109.0
C4—C2—H2B	108.6	N1—C35—H35A	109.0
H2A—C2—H2B	107.6	C34—C35—H35B	109.0
C6—C4—C5	120.5 (9)	N1—C35—H35B	109.0
C6—C4—C2	120.3 (9)	H35A—C35—H35B	107.8
C5—C4—C2	119.0 (8)	C3—N2—C37	111.9 (7)
C4—C6—C18	120.1 (10)	C3—N2—H2C	109.2
C4—C6—H6	120.0	C37—N2—H2C	109.2
C18—C6—H6	120.0	C3—N2—H2D	109.2
C4—C5—C7	118.7 (9)	C37—N2—H2D	109.2
C4—C5—H5	120.7	H2C—N2—H2D	107.9
C7—C5—H5	120.7	C17—C37—N2	111.8 (8)
C8—C7—C5	121.1 (10)	C17—C37—H37A	109.2
C8—C7—H7	119.4	N2—C37—H37A	109.2
C5—C7—H7	119.4	C17—C37—H37B	109.2
C18—C8—C7	118.7 (11)	N2—C37—H37B	109.2
C18—C8—H8	120.7	H37A—C37—H37B	107.9
C7—C8—H8	120.7	C39—C40—C11	121.3 (18)
C42—C11—C40	120.2 (16)	C39—C40—H40	119.4
C42—C11—C3	121.2 (18)	C11—C40—H40	119.4
C40—C11—C3	118.4 (15)	C11—C42—C41	117.8 (17)
C16—C17—C12	117.2 (8)	C11—C42—H42	121.1
C16—C17—C37	122.0 (9)	C41—C42—H42	121.1
C12—C17—C37	120.7 (9)	C41—C38—C39	124.0 (15)
C17—C16—C15	121.1 (9)	C41—C38—H38	118.0
C17—C16—H16	119.5	C39—C38—H38	118.0
C15—C16—H16	119.5	C40—C39—C38	120.3 (19)
C14—C13—C12	118.2 (10)	C40—C39—H39	119.8
C14—C13—H13	120.9	C38—C39—H39	119.8
C12—C13—H13	120.9	C38—C41—C42	115.8 (14)
C13—C14—C15	120.2 (10)	C38—C41—H41	122.1
C13—C14—H14	119.9	C42—C41—H41	122.1
C15—C14—H14	119.9	S1—O4—Hg1ⁱ	134.0 (4)
C16—C15—C14	119.8 (11)	N2—C3—C11	112.1 (10)
C16—C15—H15	120.1	N2—C3—H3A	109.2
C14—C15—H15	120.1	C11—C3—H3A	109.2
C17—C12—C13	123.4 (10)	N2—C3—H3B	109.2
C17—C12—H12	118.3	C11—C3—H3B	109.2
C13—C12—H12	118.3	H3A—C3—H3B	107.9
C8—C18—C6	120.8 (11)	Cl1—Hg1—Cl2	152.43 (10)
C8—C18—H18	119.6	Cl1—Hg1—O1	94.47 (15)
C6—C18—H18	119.6	Cl2—Hg1—O1	112.27 (16)
C34—C29—C30	119.7 (10)	Cl1—Hg1—O4ⁱⁱ	100.19 (18)
C34—C29—H29	120.2	Cl2—Hg1—O4ⁱⁱ	90.91 (17)
C30—C29—H29	120.2	O1—Hg1—O4ⁱⁱ	80.8 (2)

O2—S1—O1—Hg1	15.7 (4)	C30—C29—C34—C35	176.0 (10)
O3—S1—O1—Hg1	−105.6 (4)	C32—C33—C34—C29	2.1 (17)
O4—S1—O1—Hg1	135.3 (4)	C32—C33—C34—C35	−175.3 (11)
C35—N1—C2—C4	65.4 (10)	C29—C34—C35—N1	65.7 (12)
N1—C2—C4—C6	−102.6 (10)	C33—C34—C35—N1	−116.9 (10)
N1—C2—C4—C5	81.8 (10)	C2—N1—C35—C34	68.1 (10)
C5—C4—C6—C18	−0.2 (16)	C16—C17—C37—N2	62.6 (13)
C2—C4—C6—C18	−175.8 (10)	C12—C17—C37—N2	−120.4 (10)
C6—C4—C5—C7	0.2 (14)	C3—N2—C37—C17	59.3 (10)
C2—C4—C5—C7	175.9 (8)	C42—C11—C40—C39	−5 (3)
C4—C5—C7—C8	1.5 (14)	C3—C11—C40—C39	179.8 (14)
C5—C7—C8—C18	−3.3 (16)	C40—C11—C42—C41	2 (2)
C12—C17—C16—C15	0.5 (19)	C3—C11—C42—C41	177.3 (13)
C37—C17—C16—C15	177.5 (13)	C11—C40—C39—C38	8 (2)
C12—C13—C14—C15	4 (2)	C41—C38—C39—C40	−8 (3)
C17—C16—C15—C14	1 (3)	C39—C38—C41—C42	5 (2)
C13—C14—C15—C16	−3 (3)	C11—C42—C41—C38	−2 (2)
C16—C17—C12—C13	0.3 (16)	O2—S1—O4—Hg1ⁱ	−97.7 (6)
C37—C17—C12—C13	−176.8 (9)	O3—S1—O4—Hg1ⁱ	25.8 (7)
C14—C13—C12—C17	−2.5 (17)	O1—S1—O4—Hg1ⁱ	143.8 (5)
C7—C8—C18—C6	3.3 (18)	C37—N2—C3—C11	−170.1 (11)
C4—C6—C18—C8	−1.6 (19)	C42—C11—C3—N2	102.8 (16)
C34—C29—C30—C31	−0.5 (18)	C40—C11—C3—N2	−82.1 (16)
C29—C30—C31—C32	1 (2)	S1—O1—Hg1—Cl1	92.6 (3)
C30—C31—C32—C33	−1 (2)	S1—O1—Hg1—Cl2	−80.6 (3)
C34—C33—C32—C31	−1 (2)	S1—O1—Hg1—O4ⁱⁱ	−167.8 (4)
C30—C29—C34—C33	−1.3 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱⁱⁱ	0.90	2.44	2.920 (9)	114
N1—H1A···O3ⁱⁱⁱ	0.90	2.29	3.037 (10)	141
N1—H1B···O3^iv	0.90	1.90	2.766 (9)	161
N2—H2C···O4ⁱ	0.90	2.32	3.043 (10)	137
N2—H2C···O1ⁱ	0.90	2.12	2.857 (9)	139
C37—H37A···Cl2ⁱ	0.97	2.85	3.716 (10)	149

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

Experimental details

Crystal data
Chemical formula	(C₁₄H₁₆N)₂[HgCl₂(SO₄)]
M_r	764.14
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	22.8275 (5), 12.9547 (3), 10.1512 (3)
β (°)	92.095 (2)
V (Å³)	2999.94 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.41
Crystal size (mm)	0.40 × 0.25 × 0.25

Data collection
Diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	Empirical (using intensity measurements) (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.221, 0.345
No. of measured, independent and observed [I > 2σ(I)] reflections	9151, 5464, 5304
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.02
No. of reflections	5464
No. of parameters	315
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.12, −2.40

Computer programs: COLLECT (Nonius, 2003), SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.90	2.44	2.920 (9)	113.5
N1—H1A···O3ⁱ	0.90	2.29	3.037 (10)	140.8
N1—H1B···O3ⁱⁱ	0.90	1.90	2.766 (9)	161.0
N2—H2C···O4ⁱⁱⁱ	0.90	2.32	3.043 (10)	137.3
N2—H2C···O1ⁱⁱⁱ	0.90	2.12	2.857 (9)	138.8
C37—H37A···Cl2ⁱⁱⁱ	0.97	2.85	3.716 (10)	149.0

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

References

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