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

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ISSN: 2056-9890

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

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 HgII 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 ππ 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[Aghabozorg, H., Bagheri, S., Heidari, M., Ghadermazi, M. & Attar Gharamaleki, J. (2008a). Acta Cryst. E64, m1065-m1066.],b[Aghabozorg, H., Ghadermazi, M., Nakhjavan, B. & Manteghi, F. (2008b). J. Chem. Crystallogr. 38, 135-145.],c[Aghabozorg, H., Heidari, M., Bagheri, S., Attar Gharamaleki, J. & Ghadermazi, M. (2008c). Acta Cryst. E64, m874-m875.],d[Aghabozorg, H., Heidari, M., Ghadermazi, M. & Attar Gharamaleki, J. (2008d). Acta Cryst. E64, o1045-o1046.]); Pasdar et al. (2011[Pasdar, H., Shakiba, S., Aghabozorg, H. & Notash, B. (2011). Acta Cryst. E67, m587.]).

[Scheme 1]

Experimental

Crystal data
  • (C3H12N2)[Hg(C7H3NO4)2]·2H2O

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.384, Tmax = 0.746

  • 42213 measured reflections

  • 6084 independent reflections

  • 5880 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.86 e Å−3

  • Δρmin = −1.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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⋯O5iv 0.89 1.99 2.876 (3) 174
N1—H1B⋯O7 0.89 1.96 2.836 (2) 168
N1—H1C⋯O10v 0.89 1.94 2.806 (3) 165
N2—H2A⋯O9 0.89 1.93 2.802 (3) 165
N2—H2B⋯O4iv 0.89 1.96 2.845 (2) 176
N2—H2C⋯O1vi 0.89 1.96 2.809 (3) 158
C10—H10⋯O3vii 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


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 HgII 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 ππ 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.

Refinement top

H atoms of the water molecules were found in a difference Fourier map and refined isotropically with a distance restraint of O9—H9B = 0.69 (2) Å. The other H atoms were positioned geometrically and refined as riding atoms, with N—H = 0.89 (NH3), C—H = 0.93(aromatic CH), 0.98(aliphatic CH), 0.97 (CH2) and 0.96 (CH3) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at 30% probability level.
[Figure 2] Fig. 2. The packing diagram of the title compound. Hydrogen bonds are shown as blue dashed lines.
[Figure 3] Fig. 3. The packing diagram of the title compound viewed down the a-axis, showing ππ 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]·2H2OZ = 2
Mr = 642.98F(000) = 624
Triclinic, P1Dx = 2.082 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.627 (3) ÅCell parameters from 9853 reflections
b = 10.253 (4) Åθ = 2.6–30.2°
c = 13.307 (5) ŵ = 7.57 mm1
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 tube5880 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ϕ and ω scansθmax = 30.2°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.384, Tmax = 0.746k = 1414
42213 measured reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.017H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.041 w = 1/[σ2(Fo2) + (0.0168P)2 + 0.6039P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.002
6084 reflectionsΔρmax = 0.86 e Å3
306 parametersΔρmin = 1.28 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0127 (3)
Crystal data top
(C3H12N2)[Hg(C7H3NO4)2]·2H2Oγ = 65.18 (1)°
Mr = 642.98V = 1025.6 (7) Å3
Triclinic, P1Z = 2
a = 8.627 (3) ÅMo Kα radiation
b = 10.253 (4) ŵ = 7.57 mm1
c = 13.307 (5) ÅT = 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)
Tmin = 0.384, Tmax = 0.746Rint = 0.034
42213 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0171 restraint
wR(F2) = 0.041H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.86 e Å3
6084 reflectionsΔρmin = 1.28 e Å3
306 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0952 (3)0.2606 (2)0.35723 (16)0.0295 (3)
C20.1682 (2)0.33158 (18)0.41789 (14)0.0241 (3)
C30.1950 (3)0.2868 (2)0.51469 (15)0.0301 (4)
H30.17210.20960.54360.036*
C40.2562 (3)0.3584 (2)0.56779 (15)0.0326 (4)
H40.27560.32960.63260.039*
C50.2882 (2)0.4740 (2)0.52308 (15)0.0303 (4)
H50.33000.52320.55730.036*
C60.2570 (2)0.51473 (18)0.42708 (14)0.0238 (3)
C70.2786 (2)0.6458 (2)0.37671 (15)0.0284 (3)
C80.0385 (3)0.6975 (2)0.07655 (16)0.0310 (4)
C90.1281 (2)0.58638 (19)0.00393 (14)0.0254 (3)
C100.1569 (3)0.5844 (2)0.10336 (16)0.0336 (4)
H100.07340.65160.13380.040*
C110.3121 (3)0.4807 (3)0.16443 (17)0.0417 (5)
H110.33380.47680.23680.050*
C120.4349 (3)0.3832 (3)0.11813 (17)0.0377 (4)
H120.54020.31350.15890.045*
C130.3999 (2)0.38984 (19)0.01001 (15)0.0269 (3)
C140.5322 (3)0.2844 (2)0.04488 (17)0.0327 (4)
C150.9453 (3)0.0165 (2)0.18507 (18)0.0342 (4)
H15A0.98450.04880.12450.041*
H15B0.91180.11360.16150.041*
C160.7860 (3)0.0057 (2)0.26298 (16)0.0301 (3)
H160.82650.08750.29450.036*
C170.6924 (4)0.1229 (4)0.3497 (2)0.0569 (7)
H17A0.59350.10980.39590.085*
H17B0.65060.21500.32010.085*
H17C0.77360.11830.38820.085*
N10.6591 (2)0.01061 (18)0.20471 (15)0.0329 (3)
H1A0.71450.05840.15350.049*
H1B0.61810.09600.17750.049*
H1C0.56900.00290.24830.049*
N21.0926 (2)0.0202 (2)0.23407 (17)0.0392 (4)
H2A1.18500.01340.18770.059*
H2B1.12430.10980.25480.059*
H2C1.05690.04050.28910.059*
N30.19989 (19)0.44291 (15)0.37622 (11)0.0230 (3)
N40.2479 (2)0.48991 (15)0.04832 (12)0.0237 (3)
O10.0755 (2)0.15236 (17)0.39594 (15)0.0441 (4)
O20.3667 (3)0.69114 (19)0.41085 (17)0.0491 (4)
O30.0587 (3)0.31498 (18)0.27586 (13)0.0433 (4)
O40.2038 (2)0.69576 (15)0.30516 (12)0.0347 (3)
O50.1423 (2)0.79421 (18)0.03529 (14)0.0483 (4)
O60.6731 (2)0.1974 (2)0.01150 (17)0.0553 (5)
O70.4868 (2)0.29338 (18)0.14278 (13)0.0434 (4)
O80.0605 (2)0.68596 (16)0.17330 (12)0.0382 (3)
O100.4210 (3)0.9319 (3)0.3570 (2)0.0615 (6)
Hg10.179763 (10)0.496442 (7)0.218696 (5)0.03198 (4)
O91.3514 (3)0.0549 (4)0.09976 (19)0.0606 (5)
H10A0.419 (5)0.862 (4)0.370 (3)0.069 (12)*
H10B0.334 (5)0.989 (4)0.377 (3)0.052 (10)*
H9A1.293 (6)0.122 (5)0.084 (4)0.088 (17)*
H9B1.393 (9)0.001 (6)0.061 (5)0.18 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0315 (8)0.0228 (8)0.0363 (9)0.0110 (7)0.0132 (7)0.0022 (7)
C20.0247 (7)0.0204 (7)0.0261 (8)0.0076 (6)0.0089 (6)0.0038 (6)
C30.0323 (9)0.0291 (9)0.0301 (9)0.0131 (7)0.0124 (7)0.0114 (7)
C40.0351 (9)0.0380 (10)0.0260 (8)0.0133 (8)0.0151 (7)0.0099 (7)
C50.0286 (8)0.0347 (9)0.0284 (9)0.0111 (7)0.0125 (7)0.0017 (7)
C60.0223 (7)0.0220 (7)0.0260 (8)0.0076 (6)0.0078 (6)0.0019 (6)
C70.0290 (8)0.0246 (8)0.0313 (9)0.0116 (7)0.0077 (7)0.0030 (7)
C80.0365 (9)0.0218 (8)0.0345 (9)0.0084 (7)0.0163 (8)0.0045 (7)
C90.0342 (8)0.0220 (7)0.0258 (8)0.0144 (7)0.0137 (7)0.0063 (6)
C100.0464 (11)0.0361 (10)0.0287 (9)0.0232 (9)0.0186 (8)0.0111 (7)
C110.0541 (13)0.0533 (13)0.0222 (8)0.0278 (11)0.0091 (8)0.0034 (8)
C120.0392 (10)0.0416 (11)0.0283 (9)0.0173 (9)0.0014 (8)0.0032 (8)
C130.0298 (8)0.0242 (8)0.0285 (8)0.0134 (7)0.0072 (6)0.0007 (6)
C140.0327 (9)0.0227 (8)0.0429 (11)0.0102 (7)0.0127 (8)0.0013 (7)
C150.0349 (9)0.0306 (9)0.0407 (10)0.0160 (8)0.0138 (8)0.0100 (8)
C160.0316 (8)0.0293 (9)0.0314 (9)0.0125 (7)0.0130 (7)0.0060 (7)
C170.0466 (13)0.0685 (18)0.0495 (14)0.0182 (13)0.0080 (11)0.0214 (13)
N10.0321 (8)0.0284 (8)0.0394 (9)0.0107 (6)0.0157 (7)0.0054 (7)
N20.0351 (9)0.0301 (8)0.0578 (12)0.0163 (7)0.0186 (8)0.0111 (8)
N30.0256 (6)0.0198 (6)0.0219 (6)0.0070 (5)0.0082 (5)0.0028 (5)
N40.0307 (7)0.0191 (6)0.0234 (6)0.0109 (6)0.0102 (5)0.0033 (5)
O10.0553 (10)0.0321 (8)0.0602 (11)0.0265 (7)0.0287 (8)0.0140 (7)
O20.0566 (10)0.0410 (9)0.0735 (12)0.0324 (8)0.0384 (9)0.0194 (8)
O30.0666 (11)0.0395 (8)0.0414 (8)0.0293 (8)0.0320 (8)0.0098 (7)
O40.0499 (8)0.0271 (7)0.0328 (7)0.0192 (6)0.0166 (6)0.0087 (5)
O50.0521 (9)0.0334 (8)0.0470 (9)0.0010 (7)0.0262 (8)0.0068 (7)
O60.0390 (9)0.0432 (10)0.0602 (12)0.0033 (7)0.0084 (8)0.0071 (8)
O70.0461 (9)0.0327 (8)0.0399 (8)0.0019 (6)0.0187 (7)0.0054 (6)
O80.0409 (8)0.0298 (7)0.0304 (7)0.0017 (6)0.0104 (6)0.0010 (6)
O100.0463 (11)0.0377 (10)0.0917 (17)0.0187 (9)0.0075 (11)0.0200 (11)
Hg10.04592 (5)0.02638 (5)0.02169 (4)0.01097 (3)0.01378 (3)0.00471 (2)
O90.0505 (11)0.0801 (17)0.0505 (12)0.0271 (12)0.0126 (9)0.0001 (12)
Geometric parameters (Å, º) top
C1—O31.243 (2)C14—O61.230 (3)
C1—O11.250 (2)C14—O71.251 (3)
C1—C21.522 (2)C15—N21.484 (3)
C2—N31.335 (2)C15—C161.519 (3)
C2—C31.386 (2)C15—H15A0.9700
C3—C41.383 (3)C15—H15B0.9700
C3—H30.9300C16—N11.488 (2)
C4—C51.389 (3)C16—C171.509 (3)
C4—H40.9300C16—H160.9800
C5—C61.380 (3)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C6—N31.339 (2)C17—H17C0.9600
C6—C71.522 (2)N1—H1A0.8900
C7—O21.231 (2)N1—H1B0.8900
C7—O41.258 (2)N1—H1C0.8900
C8—O51.242 (2)N2—H2A0.8900
C8—O81.254 (2)N2—H2B0.8900
C8—C91.517 (3)N2—H2C0.8900
C9—N41.340 (2)N3—Hg12.1674 (14)
C9—C101.380 (3)N4—Hg12.1783 (15)
C10—C111.379 (3)O3—Hg12.4786 (16)
C10—H100.9300O4—Hg12.5159 (14)
C11—C121.375 (3)O7—Hg12.5577 (16)
C11—H110.9300O8—Hg12.3647 (15)
C12—C131.387 (3)O10—H10A0.73 (4)
C12—H120.9300O10—H10B0.72 (4)
C13—N41.338 (2)O9—H9A0.72 (5)
C13—C141.524 (3)O9—H9B0.69 (2)
O3—C1—O1126.09 (18)C17—C16—C15113.74 (19)
O3—C1—C2118.19 (16)N1—C16—H16108.4
O1—C1—C2115.71 (17)C17—C16—H16108.4
N3—C2—C3120.68 (16)C15—C16—H16108.4
N3—C2—C1117.50 (15)C16—C17—H17A109.5
C3—C2—C1121.77 (16)C16—C17—H17B109.5
C4—C3—C2119.22 (17)H17A—C17—H17B109.5
C4—C3—H3120.4C16—C17—H17C109.5
C2—C3—H3120.4H17A—C17—H17C109.5
C3—C4—C5119.17 (17)H17B—C17—H17C109.5
C3—C4—H4120.4C16—N1—H1A109.5
C5—C4—H4120.4C16—N1—H1B109.5
C6—C5—C4118.98 (17)H1A—N1—H1B109.5
C6—C5—H5120.5C16—N1—H1C109.5
C4—C5—H5120.5H1A—N1—H1C109.5
N3—C6—C5120.99 (16)H1B—N1—H1C109.5
N3—C6—C7117.26 (15)C15—N2—H2A109.5
C5—C6—C7121.70 (16)C15—N2—H2B109.5
O2—C7—O4127.38 (18)H2A—N2—H2B109.5
O2—C7—C6116.32 (17)C15—N2—H2C109.5
O4—C7—C6116.30 (16)H2A—N2—H2C109.5
O5—C8—O8124.9 (2)H2B—N2—H2C109.5
O5—C8—C9117.18 (18)C2—N3—C6120.94 (15)
O8—C8—C9117.94 (16)C2—N3—Hg1119.33 (12)
N4—C9—C10121.04 (18)C6—N3—Hg1119.53 (12)
N4—C9—C8117.12 (16)C13—N4—C9121.05 (16)
C10—C9—C8121.83 (17)C13—N4—Hg1121.45 (12)
C11—C10—C9118.54 (19)C9—N4—Hg1117.44 (12)
C11—C10—H10120.7C1—O3—Hg1111.54 (12)
C9—C10—H10120.7C7—O4—Hg1109.10 (12)
C12—C11—C10119.94 (19)C14—O7—Hg1112.51 (13)
C12—C11—H11120.0C8—O8—Hg1113.91 (13)
C10—C11—H11120.0H10A—O10—H10B110 (4)
C11—C12—C13119.3 (2)N3—Hg1—N4160.59 (6)
C11—C12—H12120.4N3—Hg1—O8126.00 (5)
C13—C12—H12120.4N4—Hg1—O873.40 (5)
N4—C13—C12120.12 (18)N3—Hg1—O371.57 (5)
N4—C13—C14118.65 (17)N4—Hg1—O3107.28 (5)
C12—C13—C14121.23 (18)O8—Hg1—O3102.19 (6)
O6—C14—O7126.1 (2)N3—Hg1—O470.34 (5)
O6—C14—C13116.7 (2)N4—Hg1—O4115.63 (5)
O7—C14—C13117.17 (17)O8—Hg1—O484.08 (5)
N2—C15—C16110.37 (17)O3—Hg1—O4136.51 (5)
N2—C15—H15A109.6N3—Hg1—O790.47 (5)
C16—C15—H15A109.6N4—Hg1—O770.12 (5)
N2—C15—H15B109.6O8—Hg1—O7143.51 (5)
C16—C15—H15B109.6O3—Hg1—O789.59 (6)
H15A—C15—H15B108.1O4—Hg1—O7110.80 (6)
N1—C16—C17109.51 (18)H9A—O9—H9B114 (7)
N1—C16—C15108.21 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9A···O5i0.72 (5)2.23 (5)2.821 (3)140 (5)
O9—H9B···O6ii0.70 (6)2.48 (7)3.017 (4)135 (8)
O10—H10A···O20.73 (4)1.99 (4)2.718 (3)170 (4)
O10—H10B···O1iii0.72 (4)2.11 (4)2.812 (3)166 (4)
N1—H1A···O5iv0.891.992.876 (3)174
N1—H1B···O70.891.962.836 (2)168
N1—H1C···O10v0.891.942.806 (3)165
N2—H2A···O90.891.932.802 (3)165
N2—H2B···O4iv0.891.962.845 (2)176
N2—H2C···O1vi0.891.962.809 (3)158
C10—H10···O3vii0.932.403.197 (3)144
C12—H12···O4i0.932.483.232 (3)138
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y, z; (iii) x, y+1, z; (iv) x+1, y1, z; (v) x, y1, z; (vi) x+1, y, z; (vii) x, y+1, z.

Experimental details

Crystal data
Chemical formula(C3H12N2)[Hg(C7H3NO4)2]·2H2O
Mr642.98
Crystal system, space groupTriclinic, 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)
V3)1025.6 (7)
Z2
Radiation typeMo Kα
µ (mm1)7.57
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.384, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
42213, 6084, 5880
Rint0.034
(sin θ/λ)max1)0.708
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.017, 0.041, 1.13
No. of reflections6084
No. of parameters306
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O9—H9A···O5i0.72 (5)2.23 (5)2.821 (3)140 (5)
O9—H9B···O6ii0.70 (6)2.48 (7)3.017 (4)135 (8)
O10—H10A···O20.73 (4)1.99 (4)2.718 (3)170 (4)
O10—H10B···O1iii0.72 (4)2.11 (4)2.812 (3)166 (4)
N1—H1A···O5iv0.891.992.876 (3)174
N1—H1B···O70.891.962.836 (2)168
N1—H1C···O10v0.891.942.806 (3)165
N2—H2A···O90.891.932.802 (3)165
N2—H2B···O4iv0.891.962.845 (2)176
N2—H2C···O1vi0.891.962.809 (3)158
C10—H10···O3vii0.932.403.197 (3)144
C12—H12···O4i0.932.483.232 (3)138
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y, z; (iii) x, y+1, z; (iv) x+1, y1, z; (v) x, y1, 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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First citationAghabozorg, H., Ghadermazi, M., Nakhjavan, B. & Manteghi, F. (2008b). J. Chem. Crystallogr. 38, 135–145.  CrossRef CAS Google Scholar
First citationAghabozorg, H., Heidari, M., Bagheri, S., Attar Gharamaleki, J. & Ghadermazi, M. (2008c). Acta Cryst. E64, m874–m875.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAghabozorg, H., Heidari, M., Ghadermazi, M. & Attar Gharamaleki, J. (2008d). Acta Cryst. E64, o1045–o1046.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationPasdar, H., Shakiba, S., Aghabozorg, H. & Notash, B. (2011). Acta Cryst. E67, m587.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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