Propane-1,3-diammonium bis­[aqua­chlorido(4-hydroxy­pyridine-2,6-di­carboxyl­ato-κ3O2,N,O6)mercurate(II)] tetra­hydrate

Aghabozorg, H.; Bagheri, S.; Heidari, M.; Ghadermazi, M.; Attar Gharamaleki, J.

doi:10.1107/S1600536808022897

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1065-m1066

doi:10.1107/S1600536808022897

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Propane-1,3-diammonium bis[aquachlorido(4-hydroxypyridine-2,6-dicarboxylato-κ³O²,N,O⁶)mercurate(II)] tetrahydrate

Hossein Aghabozorg,^a ^* Sara Bagheri,^b Mohammad Heidari,^a Mohammad Ghadermazi ^c and Jafar Attar Gharamaleki ^a

^aFaculty of Chemistry, Tarbiat Moallem University, 49 Mofateh Avenue, Tehran, Iran, ^bDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^cDepartment of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 19 June 2008; accepted 21 July 2008; online 26 July 2008)

The reaction of mercury(II) chloride dihydrate, propane-1,3-diamine and 4-hydroxypyridine-2,6-dicarboxylic acid in a 1:1:1 molar ratio in aqueous solution, resulted in the formation of the title compound, (C₃H₁₂N₂)[Hg(C₇H₃NO₅)Cl(H₂O)]₂·4H₂O or (pnH₂)[Hg(hypydc)Cl(H₂O)]₂·4H₂O (where pn is propane-1,3-diamine and hypydcH₂ is 4-hydroxypyridine-2,6-dicarboxylic acid). The metal atom is coordinated by one chloride group, one water molecule cis to the chloride ligand and one (hypydc)²⁻ ligand. The coordinated water molecule is almost perpendicular to the plane of the aromatic ring of (hypydc)²⁻. The geometry of the resulting HgClNO₃ coordination can be described as distorted square-pyramidal. This structure also contains propane-1,3-diammonium (site symmetry 2) as a counter-ion and four uncoordinated water molecules. There is a wide range of non-covalent interactions consisting of hydrogen bonding [of the types O—H⋯O, N—H⋯O and C—H⋯O, with D⋯A ranging from 2.548 (5) to 3.393 (6) Å] and ion pairing.

Related literature

For related literature, see: Aghabozorg et al. (2007 , 2008 ); Aghabozorg, Ghadermazi & Attar Gharamaleki (2006 ); Aghabozorg, Ghadermazi & Ramezanipour (2006 ); Aghabozorg, Ghasemikhah et al. (2006 ); Ramezanipour et al. (2005 ).

Experimental

Crystal data

(C₃H₁₂N₂)[Hg(C₇H₃NO₅)Cl(H₂O)]₂·4H₂O
M_r = 1018.53
Monoclinic, C 2/c
a = 29.2207 (13) Å
b = 6.7630 (3) Å
c = 15.4913 (7) Å
β = 114.5130 (10)°
V = 2785.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 11.28 mm⁻¹
T = 100 (2) K
0.11 × 0.08 × 0.07 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.284, T_max = 0.457
9362 measured reflections
3041 independent reflections
2632 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.047
S = 0.99
3041 reflections
187 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4ⁱ	0.92	1.63	2.548 (5)	173
N2—H1C⋯O3Wⁱⁱ	0.89	2.02	2.830 (5)	150
N2—H1D⋯O2Wⁱⁱⁱ	0.89	2.30	3.096 (6)	149
N2—H1E⋯O2W^iv	0.89	1.96	2.824 (6)	165
O1W—H1A⋯O5ⁱⁱ	0.82	2.08	2.854 (5)	157
O1W—H1B⋯O2^v	0.82	2.06	2.837 (6)	157
O2W—H2B⋯O1	0.85	1.98	2.771 (6)	154
O2W—H2C⋯O2^vi	0.85	1.94	2.777 (5)	169
O3W—H3A⋯O3^v	0.85	2.30	3.019 (6)	142
O3W—H3B⋯O5	0.85	1.93	2.766 (6)	169
C8—H8B⋯O1	0.97	2.45	3.393 (6)	163
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+2; (iv) x, y-1, z; (v) $[x, -y+1, z+{\script{1\over 2}}]$ ; (vi) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022897/om2244sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022897/om2244Isup2.hkl

checkCIF report

Comment top

Recently, we have defined a plan to prepare water soluble proton-transfer compounds as novel self assembled systems that can function as suitable ligands in the synthesis of metal complexes. In this regard, we have reported cases in which protons transfer from pyridine-2,6-dicarboxylic acid, pydcH₂, and benzene-1,2,4,5-tetracarboxylicacid, btcH₄, to propane-1,3-diamine (pn) and 1,10-phenanthroline, (phen). These resulted in the formation of some novel proton transfer compounds such as (pnH₂)(pydc).(pydcH₂).2.5H₂O (Aghabozorg, Ghadermazi, Ramezanipour, 2006), (pnH₂)₂(btc).2H₂O (Aghabozorg, et al., 2007) and (phenH)₄(btcH₃)₂(btcH₂) (Aghabozorg, Ghadermazi, Attar Gharamaleki, 2006). For more details and related literature see our recent review article (Aghabozorg, et al., 2008).

The molecular structure and crystal packing diagram of the title compound are presented in Figs. 1 and 2, respectively.

The Hg^II atom is five-coordinated by one chloro group, one water molecule and one 4-hydroxypyridine-2,6-dicarboxylate, or (hypydc)^2–, group which is coordinated through one pyridine N atom and two carboxylate O atoms. These distances are in good agreement with our two recently reported Hg^II structures (Aghabozorg, Ghasemikhah, Ghadermazi, et al., 2006; Ramezanipour et al., 2005).

The sum of the Cl1—Hg1—O1, O1—Hg1—N1, N1—Hg1—O4 and O4—Hg1—Cl1 bond angles equals 361.33 °, which indicates that these four atoms are almost located in the plane. As it can be seen, the O1W atom of the coordinated water molecule occupies the axial position, while the O1, O4, N1 and Cl1 atoms form the equatorial plane of the square pyramid. The O1W—Hg1—Cl1, O1W—Hg1—N1, O1W—Hg1—O1 and O1W—Hg1—O4 angles are 94.63 (7), 96.83 (11), 91.72 (9) and 82.81 (9)^°, respectively, indicating that the coordinated water molecule is located at cis position to the chloro ligand and is also almost perpendicular to the square plane of the pyramid. Therefore, the geometry of the resulting HgClNO₃ coordination can be described as distorted square pyramidal. The molecular structure of the title compound also contains propane-1,3-diammonium (site symmetry 2) as counter-ion and four uncoordinated water molecules. In the crystal structure, there is a wide range of non-covalent interactions consisting of hydrogen bonding (of the type O—H···O, N—H···O and C—H···O with D···A ranging from 2.548 (5) Å to 3.393 (6) Å) and ion pairing (Table 1).

Related literature top

For related literature, see: Aghabozorg et al. (2007, 2008); Aghabozorg, Ghadermazi & Attar Gharamaleki (2006); Aghabozorg, Ghadermazi & Ramezanipour (2006); Aghabozorg, Ghasemikhah et al. (2006); Ramezanipour et al. (2005).

Experimental top

Aqueous solutions of HgCl₂.2H₂O (76 mg, 0.2 mmol), propane-1,3-diamine (18 mg, 0.2 mmol) and 4-hydroxypyridine-2,6-dicarboxylic acid (72 mg, 0.2 mmol) were mixed in a 1:1:1 molar ratio, and the reaction mixture was heated at about 313 K for 2 h. Colourless crystals of the title compound were obtained from the solution after three weeks at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: APEX2 (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. Symmetry code A: -x + 1, y, -z + 3/2.
	Fig. 2. The crystal packing of the title compound viewed down the b axis, hydrogen bonds are shown as dashed lines.

Propane-1,3-diammonium bis[aquachlorido(4-hydroxypyridine-2,6- dicarboxylato-κ³O²,N,O⁶)mercurate(II)] tetrahydrate top

Crystal data top

(C₃H₁₂N₂)[Hg(C₇H₃NO₅)Cl(H₂O)]₂·4H₂O	F(000) = 1928
M_r = 1018.53	D_x = 2.429 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 29.2207 (13) Å	Cell parameters from 2868 reflections
b = 6.7630 (3) Å	θ = 3–27°
c = 15.4913 (7) Å	µ = 11.28 mm⁻¹
β = 114.513 (1)°	T = 100 K
V = 2785.5 (2) Å³	Prism, colourless
Z = 4	0.11 × 0.08 × 0.07 mm

Data collection top

Bruker SMART APEXII diffractometer	3041 independent reflections
Radiation source: fine-focus sealed tube	2632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −37→36
T_min = 0.284, T_max = 0.457	k = −8→8
9362 measured reflections	l = −19→19

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)] = 0.022	Hydrogen site location: mixed
wR(F²) = 0.047	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.02P)²] where P = (F_o² + 2F_c²)/3
3041 reflections	(Δ/σ)_max = 0.003
187 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.84 e Å⁻³

Crystal data top

(C₃H₁₂N₂)[Hg(C₇H₃NO₅)Cl(H₂O)]₂·4H₂O	V = 2785.5 (2) Å³
M_r = 1018.53	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 29.2207 (13) Å	µ = 11.28 mm⁻¹
b = 6.7630 (3) Å	T = 100 K
c = 15.4913 (7) Å	0.11 × 0.08 × 0.07 mm
β = 114.513 (1)°

Data collection top

Bruker SMART APEXII diffractometer	3041 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2632 reflections with I > 2σ(I)
T_min = 0.284, T_max = 0.457	R_int = 0.036
9362 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 0.99	Δρ_max = 0.79 e Å⁻³
3041 reflections	Δρ_min = −0.84 e Å⁻³
187 parameters

Special details top

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

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

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

	x	y	z	U_iso*/U_eq
Hg1	0.360437 (6)	0.72342 (2)	0.843452 (11)	0.01284 (6)
Cl1	0.40073 (4)	0.88117 (16)	0.98816 (7)	0.0205 (2)
O1	0.41510 (10)	0.6883 (4)	0.7583 (2)	0.0163 (6)
O2	0.40827 (11)	0.6472 (5)	0.6102 (2)	0.0200 (7)
O3	0.22507 (10)	0.4439 (4)	0.43123 (19)	0.0161 (6)
H3	0.2422	0.4065	0.3956	0.024*
O4	0.27295 (10)	0.6300 (4)	0.8299 (2)	0.0159 (6)
O5	0.19566 (10)	0.6269 (5)	0.7138 (2)	0.0173 (6)
N1	0.31418 (12)	0.6356 (5)	0.7000 (2)	0.0115 (7)
C1	0.33511 (15)	0.6083 (6)	0.6378 (3)	0.0118 (8)
C2	0.30679 (15)	0.5421 (6)	0.5469 (3)	0.0135 (9)
H2A	0.3218	0.5200	0.5053	0.016*
C3	0.25554 (15)	0.5084 (6)	0.5177 (3)	0.0118 (9)
C4	0.23390 (15)	0.5464 (6)	0.5813 (3)	0.0120 (8)
H4A	0.1994	0.5324	0.5627	0.014*
C5	0.26445 (15)	0.6044 (6)	0.6713 (3)	0.0113 (8)
C6	0.39097 (15)	0.6514 (6)	0.6713 (3)	0.0130 (8)
C7	0.24210 (15)	0.6239 (6)	0.7438 (3)	0.0106 (8)
N2	0.47091 (14)	0.1672 (6)	0.8789 (3)	0.0266 (9)
H1C	0.4384	0.1443	0.8438	0.040*
H1D	0.4744	0.2326	0.9311	0.040*
H1E	0.4873	0.0528	0.8949	0.040*
C8	0.49190 (17)	0.2877 (7)	0.8234 (3)	0.0254 (11)
H8A	0.5237	0.3455	0.8659	0.030*
H8B	0.4689	0.3945	0.7916	0.030*
C9	0.5000	0.1595 (9)	0.7500	0.0249 (15)
H9A	0.4711	0.0763	0.7190	0.030*
O1W	0.38232 (10)	0.3754 (4)	0.91250 (19)	0.0169 (6)
H1A	0.3582	0.3001	0.8895	0.025*
H1B	0.3848	0.3976	0.9663	0.025*
O2W	0.50594 (11)	0.7731 (4)	0.9089 (2)	0.0245 (7)
H2B	0.4842	0.7451	0.8535	0.037*
H2C	0.5315	0.7479	0.8977	0.037*
O3W	0.12234 (11)	0.6629 (5)	0.7822 (2)	0.0245 (7)
H3A	0.1428	0.6436	0.8395	0.037*
H3B	0.1438	0.6364	0.7600	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.00977 (9)	0.01538 (9)	0.01123 (8)	−0.00051 (7)	0.00222 (6)	−0.00185 (7)
Cl1	0.0158 (5)	0.0230 (6)	0.0160 (5)	0.0004 (4)	−0.0002 (4)	−0.0066 (4)
O1	0.0102 (15)	0.0221 (16)	0.0141 (15)	−0.0007 (12)	0.0025 (12)	−0.0031 (13)
O2	0.0127 (16)	0.0302 (17)	0.0187 (16)	−0.0032 (13)	0.0082 (13)	0.0011 (14)
O3	0.0106 (15)	0.0279 (17)	0.0084 (14)	−0.0034 (12)	0.0026 (12)	−0.0056 (12)
O4	0.0095 (15)	0.0257 (17)	0.0120 (15)	−0.0008 (12)	0.0038 (12)	−0.0012 (13)
O5	0.0103 (16)	0.0285 (17)	0.0128 (15)	0.0006 (13)	0.0044 (13)	−0.0003 (13)
N1	0.0085 (17)	0.0113 (16)	0.0103 (17)	−0.0020 (13)	−0.0004 (14)	−0.0009 (14)
C1	0.012 (2)	0.010 (2)	0.012 (2)	0.0019 (15)	0.0034 (17)	0.0010 (16)
C2	0.017 (2)	0.011 (2)	0.014 (2)	0.0006 (16)	0.0073 (18)	0.0031 (16)
C3	0.013 (2)	0.011 (2)	0.008 (2)	−0.0001 (16)	0.0018 (18)	0.0040 (15)
C4	0.008 (2)	0.015 (2)	0.009 (2)	0.0020 (16)	0.0006 (17)	0.0015 (16)
C5	0.010 (2)	0.011 (2)	0.014 (2)	0.0012 (15)	0.0068 (18)	0.0022 (16)
C6	0.012 (2)	0.0094 (19)	0.016 (2)	0.0002 (16)	0.0040 (18)	0.0009 (17)
C7	0.012 (2)	0.0068 (19)	0.012 (2)	0.0007 (15)	0.0039 (17)	−0.0015 (15)
N2	0.018 (2)	0.028 (2)	0.031 (2)	0.0039 (17)	0.0067 (18)	−0.0086 (18)
C8	0.013 (2)	0.017 (2)	0.033 (3)	0.0037 (18)	−0.004 (2)	−0.003 (2)
C9	0.013 (3)	0.017 (3)	0.040 (4)	0.000	0.005 (3)	0.000
O1W	0.0174 (17)	0.0173 (15)	0.0139 (15)	−0.0014 (12)	0.0046 (13)	−0.0020 (12)
O2W	0.0126 (16)	0.0283 (18)	0.0305 (18)	0.0014 (13)	0.0067 (14)	−0.0098 (15)
O3W	0.0126 (16)	0.039 (2)	0.0191 (16)	0.0034 (14)	0.0037 (14)	0.0031 (15)

Geometric parameters (Å, º) top

Hg1—N1	2.151 (3)	C2—H2A	0.9300
Hg1—Cl1	2.3151 (10)	C3—C4	1.397 (5)
Hg1—O1	2.469 (3)	C4—C5	1.365 (6)
Hg1—O1W	2.555 (3)	C4—Hg1ⁱⁱ	4.049 (4)
Hg1—O4	2.556 (3)	C4—H4A	0.9300
Hg1—C1	3.058 (4)	C5—C7	1.521 (5)
Hg1—C5	3.069 (4)	C7—Hg1ⁱⁱ	3.844 (4)
Hg1—O5ⁱ	3.117 (3)	N2—C8	1.489 (6)
Hg1—C6	3.182 (4)	N2—H1C	0.8900
Hg1—C7	3.219 (4)	N2—H1D	0.8900
Hg1—O3Wⁱ	3.700 (3)	N2—H1E	0.8900
Hg1—C7ⁱ	3.844 (4)	C8—C9	1.524 (6)
O1—C6	1.261 (5)	C8—H8A	0.9700
O2—C6	1.244 (5)	C8—H8B	0.9700
O3—C3	1.337 (5)	C9—C8ⁱⁱⁱ	1.524 (6)
O3—H3	0.9220	C9—H9A	0.9601
O4—C7	1.263 (5)	O1W—H1A	0.8205
O5—C7	1.239 (5)	O1W—H1B	0.8199
O5—Hg1ⁱⁱ	3.117 (3)	O2W—H2B	0.8500
N1—C5	1.348 (5)	O2W—H2C	0.8499
N1—C1	1.351 (5)	O3W—Hg1ⁱⁱ	3.700 (3)
C1—C2	1.379 (6)	O3W—H3A	0.8501
C1—C6	1.522 (5)	O3W—H3B	0.8501
C2—C3	1.392 (6)

N1—Hg1—Cl1	167.66 (9)	C3—O3—H3	112.8
N1—Hg1—O1	71.94 (11)	C7—O4—Hg1	110.2 (2)
Cl1—Hg1—O1	112.32 (7)	C7—O5—Hg1ⁱⁱ	117.2 (2)
N1—Hg1—O1W	96.83 (11)	C5—N1—C1	119.2 (3)
Cl1—Hg1—O1W	94.63 (7)	C5—N1—Hg1	120.9 (3)
O1—Hg1—O1W	91.72 (9)	C1—N1—Hg1	119.9 (3)
N1—Hg1—O4	70.64 (11)	N1—C1—C2	121.0 (4)
Cl1—Hg1—O4	106.43 (7)	N1—C1—C6	118.0 (3)
O1—Hg1—O4	141.18 (9)	C2—C1—C6	121.0 (4)
O1W—Hg1—O4	82.81 (9)	C2—C1—Hg1	158.4 (3)
N1—Hg1—C1	22.53 (11)	C6—C1—Hg1	80.5 (2)
Cl1—Hg1—C1	158.80 (8)	C1—C2—C3	119.6 (4)
O1—Hg1—C1	49.41 (10)	C1—C2—H2A	120.2
O1W—Hg1—C1	96.44 (10)	C3—C2—H2A	120.2
O4—Hg1—C1	92.87 (10)	O3—C3—C2	123.9 (4)
N1—Hg1—C5	22.16 (11)	O3—C3—C4	117.3 (4)
Cl1—Hg1—C5	151.22 (8)	C2—C3—C4	118.8 (4)
O1—Hg1—C5	94.09 (10)	C5—C4—C3	118.5 (4)
O1W—Hg1—C5	95.85 (10)	C5—C4—Hg1ⁱⁱ	95.5 (2)
O4—Hg1—C5	48.81 (9)	C3—C4—Hg1ⁱⁱ	131.7 (3)
C1—Hg1—C5	44.68 (10)	C5—C4—H4A	120.7
N1—Hg1—O5ⁱ	85.23 (10)	C3—C4—H4A	120.7
Cl1—Hg1—O5ⁱ	82.43 (6)	N1—C5—C4	122.7 (4)
O1—Hg1—O5ⁱ	108.22 (8)	N1—C5—C7	118.5 (3)
O1W—Hg1—O5ⁱ	159.50 (8)	C4—C5—C7	118.7 (3)
O4—Hg1—O5ⁱ	78.64 (8)	C4—C5—Hg1	159.7 (3)
C1—Hg1—O5ⁱ	93.15 (9)	C7—C5—Hg1	81.6 (2)
C5—Hg1—O5ⁱ	78.42 (9)	O2—C6—O1	126.5 (4)
N1—Hg1—C6	50.66 (11)	O2—C6—C1	116.9 (4)
Cl1—Hg1—C6	132.49 (8)	O1—C6—C1	116.6 (3)
O1—Hg1—C6	21.38 (10)	O2—C6—Hg1	169.9 (3)
O1W—Hg1—C6	95.82 (9)	O1—C6—Hg1	45.54 (19)
O4—Hg1—C6	120.80 (10)	C1—C6—Hg1	71.4 (2)
C1—Hg1—C6	28.14 (10)	O5—C7—O4	125.9 (4)
C5—Hg1—C6	72.81 (10)	O5—C7—C5	117.6 (3)
O5ⁱ—Hg1—C6	101.11 (9)	O4—C7—C5	116.5 (3)
N1—Hg1—C7	50.00 (11)	O5—C7—Hg1	165.4 (3)
Cl1—Hg1—C7	125.05 (7)	O4—C7—Hg1	48.15 (19)
O1—Hg1—C7	121.87 (9)	C5—C7—Hg1	70.6 (2)
O1W—Hg1—C7	92.32 (9)	O5—C7—Hg1ⁱⁱ	46.1 (2)
O4—Hg1—C7	21.60 (9)	O4—C7—Hg1ⁱⁱ	120.3 (3)
C1—Hg1—C7	72.52 (10)	C5—C7—Hg1ⁱⁱ	101.0 (2)
C5—Hg1—C7	27.86 (9)	Hg1—C7—Hg1ⁱⁱ	147.28 (12)
O5ⁱ—Hg1—C7	73.33 (9)	C8—N2—H1C	109.5
C6—Hg1—C7	100.66 (10)	C8—N2—H1D	109.5
N1—Hg1—O3Wⁱ	80.95 (10)	H1C—N2—H1D	109.5
Cl1—Hg1—O3Wⁱ	90.78 (6)	C8—N2—H1E	109.5
O1—Hg1—O3Wⁱ	62.42 (8)	H1C—N2—H1E	109.5
O1W—Hg1—O3Wⁱ	153.57 (8)	H1D—N2—H1E	109.5
O4—Hg1—O3Wⁱ	120.33 (8)	N2—C8—C9	110.3 (4)
C1—Hg1—O3Wⁱ	71.54 (9)	N2—C8—H8A	109.6
C5—Hg1—O3Wⁱ	91.63 (9)	C9—C8—H8A	109.6
O5ⁱ—Hg1—O3Wⁱ	46.93 (7)	N2—C8—H8B	109.6
C6—Hg1—O3Wⁱ	62.32 (9)	C9—C8—H8B	109.6
C7—Hg1—O3Wⁱ	105.62 (8)	H8A—C8—H8B	108.1
N1—Hg1—C7ⁱ	76.55 (11)	C8—C9—C8ⁱⁱⁱ	110.6 (5)
Cl1—Hg1—C7ⁱ	91.42 (6)	C8—C9—H9A	109.3
O1—Hg1—C7ⁱ	117.56 (9)	C8ⁱⁱⁱ—C9—H9A	109.6
O1W—Hg1—C7ⁱ	145.03 (9)	Hg1—O1W—H1A	111.7
O4—Hg1—C7ⁱ	62.49 (9)	Hg1—O1W—H1B	99.1
C1—Hg1—C7ⁱ	89.81 (9)	H1A—O1W—H1B	104.6
C5—Hg1—C7ⁱ	65.25 (9)	Hg1—O2W—H2B	56.6
O5ⁱ—Hg1—C7ⁱ	16.66 (8)	Hg1—O2W—H2C	150.6
C6—Hg1—C7ⁱ	105.18 (9)	H2B—O2W—H2C	95.7
C7—Hg1—C7ⁱ	56.86 (4)	Hg1ⁱⁱ—O3W—H3A	103.6
O3Wⁱ—Hg1—C7ⁱ	60.36 (7)	Hg1ⁱⁱ—O3W—H3B	48.2
C6—O1—Hg1	113.1 (2)	H3A—O3W—H3B	94.0

N1—Hg1—O1—C6	5.0 (3)	C7—Hg1—C5—C4	−175.8 (9)
Cl1—Hg1—O1—C6	−162.6 (3)	O3Wⁱ—Hg1—C5—C4	62.7 (8)
O1W—Hg1—O1—C6	101.6 (3)	C7ⁱ—Hg1—C5—C4	118.8 (8)
O4—Hg1—O1—C6	21.0 (3)	N1—Hg1—C5—C7	177.6 (4)
C1—Hg1—O1—C6	4.6 (3)	Cl1—Hg1—C5—C7	−26.9 (3)
C5—Hg1—O1—C6	5.7 (3)	O1—Hg1—C5—C7	176.0 (2)
O5ⁱ—Hg1—O1—C6	−73.5 (3)	O1W—Hg1—C5—C7	83.9 (2)
C7—Hg1—O1—C6	7.8 (3)	O4—Hg1—C5—C7	8.77 (19)
O3Wⁱ—Hg1—O1—C6	−84.1 (3)	C1—Hg1—C5—C7	177.1 (3)
C7ⁱ—Hg1—O1—C6	−58.5 (3)	O5ⁱ—Hg1—C5—C7	−76.2 (2)
N1—Hg1—O4—C7	−15.6 (3)	C6—Hg1—C5—C7	178.2 (2)
Cl1—Hg1—O4—C7	151.8 (2)	O3Wⁱ—Hg1—C5—C7	−121.5 (2)
O1—Hg1—O4—C7	−31.7 (3)	C7ⁱ—Hg1—C5—C7	−65.42 (19)
O1W—Hg1—O4—C7	−115.5 (3)	Hg1—O1—C6—O2	171.9 (3)
C1—Hg1—O4—C7	−19.3 (3)	Hg1—O1—C6—C1	−7.9 (4)
C5—Hg1—O4—C7	−11.2 (2)	N1—C1—C6—O2	−172.1 (4)
O5ⁱ—Hg1—O4—C7	73.3 (3)	C2—C1—C6—O2	8.4 (6)
C6—Hg1—O4—C7	−22.9 (3)	Hg1—C1—C6—O2	−173.9 (4)
O3Wⁱ—Hg1—O4—C7	50.9 (3)	N1—C1—C6—O1	7.8 (5)
C7ⁱ—Hg1—O4—C7	69.0 (2)	C2—C1—C6—O1	−171.7 (4)
Cl1—Hg1—N1—C5	−69.5 (6)	Hg1—C1—C6—O1	6.0 (3)
O1—Hg1—N1—C5	178.3 (3)	N1—C1—C6—Hg1	1.8 (3)
O1W—Hg1—N1—C5	88.7 (3)	C2—C1—C6—Hg1	−177.7 (4)
O4—Hg1—N1—C5	8.9 (3)	N1—Hg1—C6—O2	145.7 (18)
C1—Hg1—N1—C5	179.1 (5)	Cl1—Hg1—C6—O2	−18.5 (18)
O5ⁱ—Hg1—N1—C5	−70.8 (3)	O1—Hg1—C6—O2	−40.5 (16)
C6—Hg1—N1—C5	−179.3 (4)	O1W—Hg1—C6—O2	−120.2 (17)
C7—Hg1—N1—C5	1.4 (3)	O4—Hg1—C6—O2	154.7 (17)
O3Wⁱ—Hg1—N1—C5	−117.9 (3)	C1—Hg1—C6—O2	147.0 (18)
C7ⁱ—Hg1—N1—C5	−56.4 (3)	C5—Hg1—C6—O2	145.4 (17)
Cl1—Hg1—N1—C1	111.5 (4)	O5ⁱ—Hg1—C6—O2	71.4 (17)
O1—Hg1—N1—C1	−0.8 (3)	C7—Hg1—C6—O2	146.3 (17)
O1W—Hg1—N1—C1	−90.3 (3)	O3Wⁱ—Hg1—C6—O2	44.1 (17)
O4—Hg1—N1—C1	−170.2 (3)	C7ⁱ—Hg1—C6—O2	88.0 (17)
C5—Hg1—N1—C1	−179.1 (5)	N1—Hg1—C6—O1	−173.8 (3)
O5ⁱ—Hg1—N1—C1	110.2 (3)	Cl1—Hg1—C6—O1	22.0 (3)
C6—Hg1—N1—C1	1.6 (3)	O1W—Hg1—C6—O1	−79.8 (3)
C7—Hg1—N1—C1	−177.6 (4)	O4—Hg1—C6—O1	−164.8 (2)
O3Wⁱ—Hg1—N1—C1	63.1 (3)	C1—Hg1—C6—O1	−172.5 (4)
C7ⁱ—Hg1—N1—C1	124.6 (3)	C5—Hg1—C6—O1	−174.1 (3)
C5—N1—C1—C2	−2.5 (6)	O5ⁱ—Hg1—C6—O1	111.9 (3)
Hg1—N1—C1—C2	176.6 (3)	C7—Hg1—C6—O1	−173.2 (3)
C5—N1—C1—C6	178.0 (3)	O3Wⁱ—Hg1—C6—O1	84.6 (3)
Hg1—N1—C1—C6	−2.9 (5)	C7ⁱ—Hg1—C6—O1	128.5 (3)
C5—N1—C1—Hg1	−179.1 (5)	N1—Hg1—C6—C1	−1.3 (2)
Cl1—Hg1—C1—N1	−146.6 (3)	Cl1—Hg1—C6—C1	−165.48 (17)
O1—Hg1—C1—N1	179.0 (3)	O1—Hg1—C6—C1	172.5 (4)
O1W—Hg1—C1—N1	92.3 (3)	O1W—Hg1—C6—C1	92.8 (2)
O4—Hg1—C1—N1	9.2 (3)	O4—Hg1—C6—C1	7.7 (2)
C5—Hg1—C1—N1	0.5 (3)	C5—Hg1—C6—C1	−1.6 (2)
O5ⁱ—Hg1—C1—N1	−69.5 (3)	O5ⁱ—Hg1—C6—C1	−75.6 (2)
C6—Hg1—C1—N1	−177.4 (4)	C7—Hg1—C6—C1	−0.7 (2)
C7—Hg1—C1—N1	1.9 (3)	O3Wⁱ—Hg1—C6—C1	−102.9 (2)
O3Wⁱ—Hg1—C1—N1	−111.8 (3)	C7ⁱ—Hg1—C6—C1	−59.0 (2)
C7ⁱ—Hg1—C1—N1	−53.2 (3)	Hg1ⁱⁱ—O5—C7—O4	−99.8 (4)
N1—Hg1—C1—C2	−8.0 (7)	Hg1ⁱⁱ—O5—C7—C5	78.1 (4)
Cl1—Hg1—C1—C2	−154.6 (6)	Hg1ⁱⁱ—O5—C7—Hg1	−160.3 (10)
O1—Hg1—C1—C2	171.0 (8)	Hg1—O4—C7—O5	−162.9 (3)
O1W—Hg1—C1—C2	84.3 (8)	Hg1—O4—C7—C5	19.2 (4)
O4—Hg1—C1—C2	1.2 (8)	Hg1—O4—C7—Hg1ⁱⁱ	141.68 (15)
C5—Hg1—C1—C2	−7.5 (7)	N1—C5—C7—O5	168.5 (4)
O5ⁱ—Hg1—C1—C2	−77.5 (8)	C4—C5—C7—O5	−14.8 (5)
C6—Hg1—C1—C2	174.6 (9)	Hg1—C5—C7—O5	166.9 (3)
C7—Hg1—C1—C2	−6.1 (7)	N1—C5—C7—O4	−13.4 (5)
O3Wⁱ—Hg1—C1—C2	−119.9 (8)	C4—C5—C7—O4	163.3 (4)
C7ⁱ—Hg1—C1—C2	−61.2 (8)	Hg1—C5—C7—O4	−15.0 (3)
N1—Hg1—C1—C6	177.4 (4)	N1—C5—C7—Hg1	1.6 (3)
Cl1—Hg1—C1—C6	30.7 (4)	C4—C5—C7—Hg1	178.3 (4)
O1—Hg1—C1—C6	−3.58 (19)	N1—C5—C7—Hg1ⁱⁱ	−145.6 (3)
O1W—Hg1—C1—C6	−90.3 (2)	C4—C5—C7—Hg1ⁱⁱ	31.2 (4)
O4—Hg1—C1—C6	−173.4 (2)	Hg1—C5—C7—Hg1ⁱⁱ	−147.18 (11)
C5—Hg1—C1—C6	177.9 (3)	N1—Hg1—C7—O5	−128.0 (12)
O5ⁱ—Hg1—C1—C6	107.8 (2)	Cl1—Hg1—C7—O5	37.8 (12)
C7—Hg1—C1—C6	179.3 (2)	O1—Hg1—C7—O5	−131.5 (11)
O3Wⁱ—Hg1—C1—C6	65.5 (2)	O1W—Hg1—C7—O5	135.1 (11)
C7ⁱ—Hg1—C1—C6	124.2 (2)	O4—Hg1—C7—O5	71.4 (11)
N1—C1—C2—C3	2.0 (6)	C1—Hg1—C7—O5	−128.9 (11)
C6—C1—C2—C3	−178.5 (4)	C5—Hg1—C7—O5	−126.8 (12)
Hg1—C1—C2—C3	7.7 (10)	O5ⁱ—Hg1—C7—O5	−30.0 (11)
C1—C2—C3—O3	−179.8 (4)	C6—Hg1—C7—O5	−128.6 (11)
C1—C2—C3—C4	1.1 (6)	O3Wⁱ—Hg1—C7—O5	−64.6 (11)
O3—C3—C4—C5	177.3 (4)	C7ⁱ—Hg1—C7—O5	−27.3 (10)
C2—C3—C4—C5	−3.6 (6)	N1—Hg1—C7—O4	160.7 (3)
O3—C3—C4—Hg1ⁱⁱ	48.2 (5)	Cl1—Hg1—C7—O4	−33.6 (3)
C2—C3—C4—Hg1ⁱⁱ	−132.7 (3)	O1—Hg1—C7—O4	157.2 (2)
C1—N1—C5—C4	−0.2 (6)	O1W—Hg1—C7—O4	63.7 (3)
Hg1—N1—C5—C4	−179.2 (3)	C1—Hg1—C7—O4	159.7 (3)
C1—N1—C5—C7	176.4 (3)	C5—Hg1—C7—O4	161.8 (4)
Hg1—N1—C5—C7	−2.7 (5)	O5ⁱ—Hg1—C7—O4	−101.4 (3)
C1—N1—C5—Hg1	179.1 (5)	C6—Hg1—C7—O4	160.1 (3)
C3—C4—C5—N1	3.2 (6)	O3Wⁱ—Hg1—C7—O4	−135.9 (2)
Hg1ⁱⁱ—C4—C5—N1	147.6 (3)	C7ⁱ—Hg1—C7—O4	−98.7 (3)
C3—C4—C5—C7	−173.3 (3)	N1—Hg1—C7—C5	−1.2 (2)
Hg1ⁱⁱ—C4—C5—C7	−29.0 (4)	Cl1—Hg1—C7—C5	164.56 (18)
C3—C4—C5—Hg1	1.9 (10)	O1—Hg1—C7—C5	−4.7 (2)
Hg1ⁱⁱ—C4—C5—Hg1	146.3 (7)	O1W—Hg1—C7—C5	−98.1 (2)
Cl1—Hg1—C5—N1	155.4 (3)	O4—Hg1—C7—C5	−161.8 (4)
O1—Hg1—C5—N1	−1.6 (3)	C1—Hg1—C7—C5	−2.1 (2)
O1W—Hg1—C5—N1	−93.8 (3)	O5ⁱ—Hg1—C7—C5	96.8 (2)
O4—Hg1—C5—N1	−168.9 (3)	C6—Hg1—C7—C5	−1.8 (2)
C1—Hg1—C5—N1	−0.5 (3)	O3Wⁱ—Hg1—C7—C5	62.2 (2)
O5ⁱ—Hg1—C5—N1	106.2 (3)	C7ⁱ—Hg1—C7—C5	99.5 (2)
C6—Hg1—C5—N1	0.5 (3)	N1—Hg1—C7—Hg1ⁱⁱ	78.7 (2)
C7—Hg1—C5—N1	−177.6 (4)	Cl1—Hg1—C7—Hg1ⁱⁱ	−115.6 (2)
O3Wⁱ—Hg1—C5—N1	60.9 (3)	O1—Hg1—C7—Hg1ⁱⁱ	75.2 (2)
C7ⁱ—Hg1—C5—N1	116.9 (3)	O1W—Hg1—C7—Hg1ⁱⁱ	−18.3 (2)
N1—Hg1—C5—C4	1.9 (7)	O4—Hg1—C7—Hg1ⁱⁱ	−82.0 (3)
Cl1—Hg1—C5—C4	157.3 (7)	C1—Hg1—C7—Hg1ⁱⁱ	77.8 (2)
O1—Hg1—C5—C4	0.2 (8)	C5—Hg1—C7—Hg1ⁱⁱ	79.9 (3)
O1W—Hg1—C5—C4	−91.9 (8)	O5ⁱ—Hg1—C7—Hg1ⁱⁱ	176.6 (2)
O4—Hg1—C5—C4	−167.0 (9)	C6—Hg1—C7—Hg1ⁱⁱ	78.1 (2)
C1—Hg1—C5—C4	1.3 (8)	O3Wⁱ—Hg1—C7—Hg1ⁱⁱ	142.1 (2)
O5ⁱ—Hg1—C5—C4	108.0 (8)	C7ⁱ—Hg1—C7—Hg1ⁱⁱ	179.4 (3)
C6—Hg1—C5—C4	2.4 (8)	N2—C8—C9—C8ⁱⁱⁱ	165.1 (4)

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4^iv	0.92	1.63	2.548 (5)	173
N2—H1C···O3Wⁱⁱ	0.89	2.03	2.830 (5)	150
N2—H1D···O2W^v	0.89	2.30	3.096 (6)	149
N2—H1E···O2W^vi	0.89	1.96	2.824 (6)	165
O1W—H1A···O5ⁱⁱ	0.82	2.08	2.854 (5)	157
O1W—H1B···O2^vii	0.82	2.07	2.837 (6)	157
O2W—H2B···O1	0.85	1.98	2.771 (6)	154
O2W—H2C···O2ⁱⁱⁱ	0.85	1.94	2.777 (5)	169
O3W—H3A···O3^vii	0.85	2.30	3.019 (6)	142
O3W—H3B···O5	0.85	1.93	2.766 (6)	169
C8—H8B···O1	0.97	2.45	3.393 (6)	163

Symmetry codes: (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1, y, −z+3/2; (iv) x, −y+1, z−1/2; (v) −x+1, −y+1, −z+2; (vi) x, y−1, z; (vii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	(C₃H₁₂N₂)[Hg(C₇H₃NO₅)Cl(H₂O)]₂·4H₂O
M_r	1018.53
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	29.2207 (13), 6.7630 (3), 15.4913 (7)
β (°)	114.513 (1)
V (Å³)	2785.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	11.28
Crystal size (mm)	0.11 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.284, 0.457
No. of measured, independent and observed [I > 2σ(I)] reflections	9362, 3041, 2632
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.047, 0.99
No. of reflections	3041
No. of parameters	187
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.84

Computer programs: APEX2 (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.92	1.631	2.548 (5)	173
N2—H1C···O3Wⁱⁱ	0.89	2.025	2.830 (5)	150
N2—H1D···O2Wⁱⁱⁱ	0.89	2.301	3.096 (6)	149
N2—H1E···O2W^iv	0.89	1.955	2.824 (6)	165
O1W—H1A···O5ⁱⁱ	0.82	2.079	2.854 (5)	157
O1W—H1B···O2^v	0.82	2.065	2.837 (6)	157
O2W—H2B···O1	0.85	1.983	2.771 (6)	154
O2W—H2C···O2^vi	0.85	1.939	2.777 (5)	169
O3W—H3A···O3^v	0.85	2.304	3.019 (6)	142
O3W—H3B···O5	0.85	1.926	2.766 (6)	169
C8—H8B···O1	0.97	2.45	3.393 (6)	163

Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+2; (iv) x, y−1, z; (v) x, −y+1, z+1/2; (vi) −x+1, y, −z+3/2.

References

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