Propane-1,2-diaminium bis­(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)mercurate(II) dihydrate

Agah, A.A.; Saadati Moshtaghin, H.R.; Notash, B.; Amiri Rudbari, H.; Bruno, G.

doi:10.1107/S1600536811024366

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m983

doi:10.1107/S1600536811024366

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Propane-1,2-diaminium bis(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)mercurate(II) dihydrate

Ali Akbar Agah,^a ^* Hamid Reza Saadati Moshtaghin,^a Behrouz Notash,^b Hadi Amiri Rudbari ^c and Giuseppe Bruno ^c

^aFaculty of Chemistry, Tarbiat Moallem University, 15614 Tehran, Iran, ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran, and ^cDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Universita di Messina, 98166 Messina, Italy
^*Correspondence e-mail: agah2006@yahoo.com

(Received 19 May 2011; accepted 21 June 2011; online 25 June 2011)

In the title compound, (C₃H₁₂N₂)[Hg(C₇H₃NO₄)₂]·2H₂O, the Hg^II ion is coordinated by four O and two N atoms of two pyridine-2,6-dicarboxylate (pydc) ligands in a distorted octahedral environment. The structure contains two uncoordinated water molecules. In the crystal, N—H⋯O, O—H⋯O and weak C—H⋯O hydrogen bonds and π–π stacking interactions between the pyridine rings of the pydc ligands, with a centroid–centroid distance of 3.4582 (18) Å, stabilize the structure.

Related literature

For related structures, see: Aghabozorg et al. (2008a ,b ,c ,d ); Pasdar et al. (2011 ).

Experimental

Crystal data

(C₃H₁₂N₂)[Hg(C₇H₃NO₄)₂]·2H₂O
M_r = 642.98
Triclinic, $[P \overline 1]$
a = 8.627 (3) Å
b = 10.253 (4) Å
c = 13.307 (5) Å
α = 86.33 (1)°
β = 74.08 (2)°
γ = 65.18 (1)°
V = 1025.6 (7) Å³
Z = 2
Mo Kα radiation
μ = 7.57 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.384, T_max = 0.746
42213 measured reflections
6084 independent reflections
5880 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.017
wR(F²) = 0.041
S = 1.13
6084 reflections
306 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.86 e Å⁻³
Δρ_min = −1.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9A⋯O5ⁱ	0.72 (5)	2.23 (5)	2.821 (3)	140 (5)
O9—H9B⋯O6ⁱⁱ	0.70 (6)	2.48 (7)	3.017 (4)	135 (8)
O10—H10A⋯O2	0.73 (4)	1.99 (4)	2.718 (3)	170 (4)
O10—H10B⋯O1ⁱⁱⁱ	0.72 (4)	2.11 (4)	2.812 (3)	166 (4)
N1—H1A⋯O5^iv	0.89	1.99	2.876 (3)	174
N1—H1B⋯O7	0.89	1.96	2.836 (2)	168
N1—H1C⋯O10^v	0.89	1.94	2.806 (3)	165
N2—H2A⋯O9	0.89	1.93	2.802 (3)	165
N2—H2B⋯O4^iv	0.89	1.96	2.845 (2)	176
N2—H2C⋯O1^vi	0.89	1.96	2.809 (3)	158
C10—H10⋯O3^vii	0.93	2.40	3.197 (3)	144
C12—H12⋯O4ⁱ	0.93	2.48	3.232 (3)	138
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y, -z; (iii) x, y+1, z; (iv) x+1, y-1, z; (v) x, y-1, z; (vi) x+1, y, z; (vii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024366/hy2434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024366/hy2434Isup2.hkl

checkCIF report

Comment top

Our research group has previously reported several proton-transfer compounds using pyridine-2,6-dicarboxylic acid (pydcH₂), propane-1,2-diamine (p-1,2-da) and propane-1,3-diamine (p-1,3-da), including (p-1,2-daH₂)(pydcH)₂.2H₂O (Aghabozorg et al., 2008d), (p-1,3-daH₂)[Cd(pydc)₂].3.5H₂O (Aghabozorg et al., 2008b), (p-1,2-daH₂)[Ni(pydc)₂].4H₂O (Aghabozorg et al., 2008c), (p-1,3-daH₂)[Hg(hypydc)Cl(H₂O)]₂.4H₂O (hypydcH₂ = 4-hydroxypyridine-2,6-dicarboxylic acid) (Aghabozorg et al., 2008a) and (p-1,2-daH₂)[Zr(pydc)₃].3H₂O (Pasdar et al., 2011).

The molecular structure of the title compound is shown in Fig. 1. The Hg^II ion is six-coordinated by two pydc ligands in a distorted octahedral environment. In the crystal structure, there are intermolecular N—H···O, O—H···O and weak C—H···O hydrogen bonds (Fig. 2, Table 1). There are also π–π stacking interactions between the pyridine rings of the pydc ligands, with a centroid–centroid distance of 3.4582 (18) Å (Fig. 2). These noncovalent interactions play an important role in the stabilization of the crystal structure.

Related literature top

For related structures, see: Aghabozorg et al. (2008a,b,c,d); Pasdar et al. (2011).

Experimental top

A mixture of an aqueous solution (30 ml) of propane-1,2-diamine (1 mmol), pyridine-2,6-dicarboxylic acid (2 mmol) and mercury(II) nitrate (1 mmol) were stirred at room temperature. Crystals of the title compound were obtained after three weeks at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The packing diagram of the title compound. Hydrogen bonds are shown as blue dashed lines.
	Fig. 3. The packing diagram of the title compound viewed down the a-axis, showing π–π interactions between the pydc ligands [centroid–centroid distance = 3.4582 (18) Å]. Only anionic parts are shown for clarity.

Propane-1,2-diaminium bis(pyridine-2,6-dicarboxylato- κ³O²,N,O⁶)mercurate(II) dihydrate top

Crystal data top

(C₃H₁₂N₂)[Hg(C₇H₃NO₄)₂]·2H₂O	Z = 2
M_r = 642.98	F(000) = 624
Triclinic, P1	D_x = 2.082 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.627 (3) Å	Cell parameters from 9853 reflections
b = 10.253 (4) Å	θ = 2.6–30.2°
c = 13.307 (5) Å	µ = 7.57 mm⁻¹
α = 86.33 (1)°	T = 293 K
β = 74.08 (2)°	Block, yellow
γ = 65.18 (1)°	0.40 × 0.30 × 0.20 mm
V = 1025.6 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	6084 independent reflections
Radiation source: fine-focus sealed tube	5880 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 30.2°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.384, T_max = 0.746	k = −14→14
42213 measured reflections	l = −18→18

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)] = 0.017	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.041	w = 1/[σ²(F_o²) + (0.0168P)² + 0.6039P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.002
6084 reflections	Δρ_max = 0.86 e Å⁻³
306 parameters	Δρ_min = −1.28 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0127 (3)

Crystal data top

(C₃H₁₂N₂)[Hg(C₇H₃NO₄)₂]·2H₂O	γ = 65.18 (1)°
M_r = 642.98	V = 1025.6 (7) Å³
Triclinic, P1	Z = 2
a = 8.627 (3) Å	Mo Kα radiation
b = 10.253 (4) Å	µ = 7.57 mm⁻¹
c = 13.307 (5) Å	T = 293 K
α = 86.33 (1)°	0.40 × 0.30 × 0.20 mm
β = 74.08 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6084 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5880 reflections with I > 2σ(I)
T_min = 0.384, T_max = 0.746	R_int = 0.034
42213 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	1 restraint
wR(F²) = 0.041	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.86 e Å⁻³
6084 reflections	Δρ_min = −1.28 e Å⁻³
306 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.0952 (3)	0.2606 (2)	0.35723 (16)	0.0295 (3)
C2	0.1682 (2)	0.33158 (18)	0.41789 (14)	0.0241 (3)
C3	0.1950 (3)	0.2868 (2)	0.51469 (15)	0.0301 (4)
H3	0.1721	0.2096	0.5436	0.036*
C4	0.2562 (3)	0.3584 (2)	0.56779 (15)	0.0326 (4)
H4	0.2756	0.3296	0.6326	0.039*
C5	0.2882 (2)	0.4740 (2)	0.52308 (15)	0.0303 (4)
H5	0.3300	0.5232	0.5573	0.036*
C6	0.2570 (2)	0.51473 (18)	0.42708 (14)	0.0238 (3)
C7	0.2786 (2)	0.6458 (2)	0.37671 (15)	0.0284 (3)
C8	−0.0385 (3)	0.6975 (2)	0.07655 (16)	0.0310 (4)
C9	0.1281 (2)	0.58638 (19)	0.00393 (14)	0.0254 (3)
C10	0.1569 (3)	0.5844 (2)	−0.10336 (16)	0.0336 (4)
H10	0.0734	0.6516	−0.1338	0.040*
C11	0.3121 (3)	0.4807 (3)	−0.16443 (17)	0.0417 (5)
H11	0.3338	0.4768	−0.2368	0.050*
C12	0.4349 (3)	0.3832 (3)	−0.11813 (17)	0.0377 (4)
H12	0.5402	0.3135	−0.1589	0.045*
C13	0.3999 (2)	0.38984 (19)	−0.01001 (15)	0.0269 (3)
C14	0.5322 (3)	0.2844 (2)	0.04488 (17)	0.0327 (4)
C15	0.9453 (3)	0.0165 (2)	0.18507 (18)	0.0342 (4)
H15A	0.9845	−0.0488	0.1245	0.041*
H15B	0.9118	0.1136	0.1615	0.041*
C16	0.7860 (3)	0.0057 (2)	0.26298 (16)	0.0301 (3)
H16	0.8265	−0.0875	0.2945	0.036*
C17	0.6924 (4)	0.1229 (4)	0.3497 (2)	0.0569 (7)
H17A	0.5935	0.1098	0.3959	0.085*
H17B	0.6506	0.2150	0.3201	0.085*
H17C	0.7736	0.1183	0.3882	0.085*
N1	0.6591 (2)	0.01061 (18)	0.20471 (15)	0.0329 (3)
H1A	0.7145	−0.0584	0.1535	0.049*
H1B	0.6181	0.0960	0.1775	0.049*
H1C	0.5690	−0.0029	0.2483	0.049*
N2	1.0926 (2)	−0.0202 (2)	0.23407 (17)	0.0392 (4)
H2A	1.1850	−0.0134	0.1877	0.059*
H2B	1.1243	−0.1098	0.2548	0.059*
H2C	1.0569	0.0405	0.2891	0.059*
N3	0.19989 (19)	0.44291 (15)	0.37622 (11)	0.0230 (3)
N4	0.2479 (2)	0.48991 (15)	0.04832 (12)	0.0237 (3)
O1	0.0755 (2)	0.15236 (17)	0.39594 (15)	0.0441 (4)
O2	0.3667 (3)	0.69114 (19)	0.41085 (17)	0.0491 (4)
O3	0.0587 (3)	0.31498 (18)	0.27586 (13)	0.0433 (4)
O4	0.2038 (2)	0.69576 (15)	0.30516 (12)	0.0347 (3)
O5	−0.1423 (2)	0.79421 (18)	0.03529 (14)	0.0483 (4)
O6	0.6731 (2)	0.1974 (2)	−0.01150 (17)	0.0553 (5)
O7	0.4868 (2)	0.29338 (18)	0.14278 (13)	0.0434 (4)
O8	−0.0605 (2)	0.68596 (16)	0.17330 (12)	0.0382 (3)
O10	0.4210 (3)	0.9319 (3)	0.3570 (2)	0.0615 (6)
Hg1	0.179763 (10)	0.496442 (7)	0.218696 (5)	0.03198 (4)
O9	1.3514 (3)	0.0549 (4)	0.09976 (19)	0.0606 (5)
H10A	0.419 (5)	0.862 (4)	0.370 (3)	0.069 (12)*
H10B	0.334 (5)	0.989 (4)	0.377 (3)	0.052 (10)*
H9A	1.293 (6)	0.122 (5)	0.084 (4)	0.088 (17)*
H9B	1.393 (9)	−0.001 (6)	0.061 (5)	0.18 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0315 (8)	0.0228 (8)	0.0363 (9)	−0.0110 (7)	−0.0132 (7)	0.0022 (7)
C2	0.0247 (7)	0.0204 (7)	0.0261 (8)	−0.0076 (6)	−0.0089 (6)	0.0038 (6)
C3	0.0323 (9)	0.0291 (9)	0.0301 (9)	−0.0131 (7)	−0.0124 (7)	0.0114 (7)
C4	0.0351 (9)	0.0380 (10)	0.0260 (8)	−0.0133 (8)	−0.0151 (7)	0.0099 (7)
C5	0.0286 (8)	0.0347 (9)	0.0284 (9)	−0.0111 (7)	−0.0125 (7)	0.0017 (7)
C6	0.0223 (7)	0.0220 (7)	0.0260 (8)	−0.0076 (6)	−0.0078 (6)	0.0019 (6)
C7	0.0290 (8)	0.0246 (8)	0.0313 (9)	−0.0116 (7)	−0.0077 (7)	0.0030 (7)
C8	0.0365 (9)	0.0218 (8)	0.0345 (9)	−0.0084 (7)	−0.0163 (8)	0.0045 (7)
C9	0.0342 (8)	0.0220 (7)	0.0258 (8)	−0.0144 (7)	−0.0137 (7)	0.0063 (6)
C10	0.0464 (11)	0.0361 (10)	0.0287 (9)	−0.0232 (9)	−0.0186 (8)	0.0111 (7)
C11	0.0541 (13)	0.0533 (13)	0.0222 (8)	−0.0278 (11)	−0.0091 (8)	0.0034 (8)
C12	0.0392 (10)	0.0416 (11)	0.0283 (9)	−0.0173 (9)	−0.0014 (8)	−0.0032 (8)
C13	0.0298 (8)	0.0242 (8)	0.0285 (8)	−0.0134 (7)	−0.0072 (6)	0.0007 (6)
C14	0.0327 (9)	0.0227 (8)	0.0429 (11)	−0.0102 (7)	−0.0127 (8)	0.0013 (7)
C15	0.0349 (9)	0.0306 (9)	0.0407 (10)	−0.0160 (8)	−0.0138 (8)	0.0100 (8)
C16	0.0316 (8)	0.0293 (9)	0.0314 (9)	−0.0125 (7)	−0.0130 (7)	0.0060 (7)
C17	0.0466 (13)	0.0685 (18)	0.0495 (14)	−0.0182 (13)	−0.0080 (11)	−0.0214 (13)
N1	0.0321 (8)	0.0284 (8)	0.0394 (9)	−0.0107 (6)	−0.0157 (7)	0.0054 (7)
N2	0.0351 (9)	0.0301 (8)	0.0578 (12)	−0.0163 (7)	−0.0186 (8)	0.0111 (8)
N3	0.0256 (6)	0.0198 (6)	0.0219 (6)	−0.0070 (5)	−0.0082 (5)	0.0028 (5)
N4	0.0307 (7)	0.0191 (6)	0.0234 (6)	−0.0109 (6)	−0.0102 (5)	0.0033 (5)
O1	0.0553 (10)	0.0321 (8)	0.0602 (11)	−0.0265 (7)	−0.0287 (8)	0.0140 (7)
O2	0.0566 (10)	0.0410 (9)	0.0735 (12)	−0.0324 (8)	−0.0384 (9)	0.0194 (8)
O3	0.0666 (11)	0.0395 (8)	0.0414 (8)	−0.0293 (8)	−0.0320 (8)	0.0098 (7)
O4	0.0499 (8)	0.0271 (7)	0.0328 (7)	−0.0192 (6)	−0.0166 (6)	0.0087 (5)
O5	0.0521 (9)	0.0334 (8)	0.0470 (9)	0.0010 (7)	−0.0262 (8)	0.0068 (7)
O6	0.0390 (9)	0.0432 (10)	0.0602 (12)	0.0033 (7)	−0.0084 (8)	−0.0071 (8)
O7	0.0461 (9)	0.0327 (8)	0.0399 (8)	−0.0019 (6)	−0.0187 (7)	0.0054 (6)
O8	0.0409 (8)	0.0298 (7)	0.0304 (7)	−0.0017 (6)	−0.0104 (6)	0.0010 (6)
O10	0.0463 (11)	0.0377 (10)	0.0917 (17)	−0.0187 (9)	−0.0075 (11)	0.0200 (11)
Hg1	0.04592 (5)	0.02638 (5)	0.02169 (4)	−0.01097 (3)	−0.01378 (3)	0.00471 (2)
O9	0.0505 (11)	0.0801 (17)	0.0505 (12)	−0.0271 (12)	−0.0126 (9)	0.0001 (12)

Geometric parameters (Å, º) top

C1—O3	1.243 (2)	C14—O6	1.230 (3)
C1—O1	1.250 (2)	C14—O7	1.251 (3)
C1—C2	1.522 (2)	C15—N2	1.484 (3)
C2—N3	1.335 (2)	C15—C16	1.519 (3)
C2—C3	1.386 (2)	C15—H15A	0.9700
C3—C4	1.383 (3)	C15—H15B	0.9700
C3—H3	0.9300	C16—N1	1.488 (2)
C4—C5	1.389 (3)	C16—C17	1.509 (3)
C4—H4	0.9300	C16—H16	0.9800
C5—C6	1.380 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—N3	1.339 (2)	C17—H17C	0.9600
C6—C7	1.522 (2)	N1—H1A	0.8900
C7—O2	1.231 (2)	N1—H1B	0.8900
C7—O4	1.258 (2)	N1—H1C	0.8900
C8—O5	1.242 (2)	N2—H2A	0.8900
C8—O8	1.254 (2)	N2—H2B	0.8900
C8—C9	1.517 (3)	N2—H2C	0.8900
C9—N4	1.340 (2)	N3—Hg1	2.1674 (14)
C9—C10	1.380 (3)	N4—Hg1	2.1783 (15)
C10—C11	1.379 (3)	O3—Hg1	2.4786 (16)
C10—H10	0.9300	O4—Hg1	2.5159 (14)
C11—C12	1.375 (3)	O7—Hg1	2.5577 (16)
C11—H11	0.9300	O8—Hg1	2.3647 (15)
C12—C13	1.387 (3)	O10—H10A	0.73 (4)
C12—H12	0.9300	O10—H10B	0.72 (4)
C13—N4	1.338 (2)	O9—H9A	0.72 (5)
C13—C14	1.524 (3)	O9—H9B	0.69 (2)

O3—C1—O1	126.09 (18)	C17—C16—C15	113.74 (19)
O3—C1—C2	118.19 (16)	N1—C16—H16	108.4
O1—C1—C2	115.71 (17)	C17—C16—H16	108.4
N3—C2—C3	120.68 (16)	C15—C16—H16	108.4
N3—C2—C1	117.50 (15)	C16—C17—H17A	109.5
C3—C2—C1	121.77 (16)	C16—C17—H17B	109.5
C4—C3—C2	119.22 (17)	H17A—C17—H17B	109.5
C4—C3—H3	120.4	C16—C17—H17C	109.5
C2—C3—H3	120.4	H17A—C17—H17C	109.5
C3—C4—C5	119.17 (17)	H17B—C17—H17C	109.5
C3—C4—H4	120.4	C16—N1—H1A	109.5
C5—C4—H4	120.4	C16—N1—H1B	109.5
C6—C5—C4	118.98 (17)	H1A—N1—H1B	109.5
C6—C5—H5	120.5	C16—N1—H1C	109.5
C4—C5—H5	120.5	H1A—N1—H1C	109.5
N3—C6—C5	120.99 (16)	H1B—N1—H1C	109.5
N3—C6—C7	117.26 (15)	C15—N2—H2A	109.5
C5—C6—C7	121.70 (16)	C15—N2—H2B	109.5
O2—C7—O4	127.38 (18)	H2A—N2—H2B	109.5
O2—C7—C6	116.32 (17)	C15—N2—H2C	109.5
O4—C7—C6	116.30 (16)	H2A—N2—H2C	109.5
O5—C8—O8	124.9 (2)	H2B—N2—H2C	109.5
O5—C8—C9	117.18 (18)	C2—N3—C6	120.94 (15)
O8—C8—C9	117.94 (16)	C2—N3—Hg1	119.33 (12)
N4—C9—C10	121.04 (18)	C6—N3—Hg1	119.53 (12)
N4—C9—C8	117.12 (16)	C13—N4—C9	121.05 (16)
C10—C9—C8	121.83 (17)	C13—N4—Hg1	121.45 (12)
C11—C10—C9	118.54 (19)	C9—N4—Hg1	117.44 (12)
C11—C10—H10	120.7	C1—O3—Hg1	111.54 (12)
C9—C10—H10	120.7	C7—O4—Hg1	109.10 (12)
C12—C11—C10	119.94 (19)	C14—O7—Hg1	112.51 (13)
C12—C11—H11	120.0	C8—O8—Hg1	113.91 (13)
C10—C11—H11	120.0	H10A—O10—H10B	110 (4)
C11—C12—C13	119.3 (2)	N3—Hg1—N4	160.59 (6)
C11—C12—H12	120.4	N3—Hg1—O8	126.00 (5)
C13—C12—H12	120.4	N4—Hg1—O8	73.40 (5)
N4—C13—C12	120.12 (18)	N3—Hg1—O3	71.57 (5)
N4—C13—C14	118.65 (17)	N4—Hg1—O3	107.28 (5)
C12—C13—C14	121.23 (18)	O8—Hg1—O3	102.19 (6)
O6—C14—O7	126.1 (2)	N3—Hg1—O4	70.34 (5)
O6—C14—C13	116.7 (2)	N4—Hg1—O4	115.63 (5)
O7—C14—C13	117.17 (17)	O8—Hg1—O4	84.08 (5)
N2—C15—C16	110.37 (17)	O3—Hg1—O4	136.51 (5)
N2—C15—H15A	109.6	N3—Hg1—O7	90.47 (5)
C16—C15—H15A	109.6	N4—Hg1—O7	70.12 (5)
N2—C15—H15B	109.6	O8—Hg1—O7	143.51 (5)
C16—C15—H15B	109.6	O3—Hg1—O7	89.59 (6)
H15A—C15—H15B	108.1	O4—Hg1—O7	110.80 (6)
N1—C16—C17	109.51 (18)	H9A—O9—H9B	114 (7)
N1—C16—C15	108.21 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O5ⁱ	0.72 (5)	2.23 (5)	2.821 (3)	140 (5)
O9—H9B···O6ⁱⁱ	0.70 (6)	2.48 (7)	3.017 (4)	135 (8)
O10—H10A···O2	0.73 (4)	1.99 (4)	2.718 (3)	170 (4)
O10—H10B···O1ⁱⁱⁱ	0.72 (4)	2.11 (4)	2.812 (3)	166 (4)
N1—H1A···O5^iv	0.89	1.99	2.876 (3)	174
N1—H1B···O7	0.89	1.96	2.836 (2)	168
N1—H1C···O10^v	0.89	1.94	2.806 (3)	165
N2—H2A···O9	0.89	1.93	2.802 (3)	165
N2—H2B···O4^iv	0.89	1.96	2.845 (2)	176
N2—H2C···O1^vi	0.89	1.96	2.809 (3)	158
C10—H10···O3^vii	0.93	2.40	3.197 (3)	144
C12—H12···O4ⁱ	0.93	2.48	3.232 (3)	138

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

Experimental details

Crystal data
Chemical formula	(C₃H₁₂N₂)[Hg(C₇H₃NO₄)₂]·2H₂O
M_r	642.98
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.627 (3), 10.253 (4), 13.307 (5)
α, β, γ (°)	86.33 (1), 74.08 (2), 65.18 (1)
V (Å³)	1025.6 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.57
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.384, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	42213, 6084, 5880
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.041, 1.13
No. of reflections	6084
No. of parameters	306
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.86, −1.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O5ⁱ	0.72 (5)	2.23 (5)	2.821 (3)	140 (5)
O9—H9B···O6ⁱⁱ	0.70 (6)	2.48 (7)	3.017 (4)	135 (8)
O10—H10A···O2	0.73 (4)	1.99 (4)	2.718 (3)	170 (4)
O10—H10B···O1ⁱⁱⁱ	0.72 (4)	2.11 (4)	2.812 (3)	166 (4)
N1—H1A···O5^iv	0.89	1.99	2.876 (3)	174
N1—H1B···O7	0.89	1.96	2.836 (2)	168
N1—H1C···O10^v	0.89	1.94	2.806 (3)	165
N2—H2A···O9	0.89	1.93	2.802 (3)	165
N2—H2B···O4^iv	0.89	1.96	2.845 (2)	176
N2—H2C···O1^vi	0.89	1.96	2.809 (3)	158
C10—H10···O3^vii	0.93	2.40	3.197 (3)	144
C12—H12···O4ⁱ	0.93	2.48	3.232 (3)	138

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

Acknowledgements

We are grateful to Tarbiat Moallem University for financial support.

References

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