Propane-1,2-diaminium bis-(pyridine-2,6-dicarboxyl-ato-κO,N,O)mercurate(II) dihydrate.

In the title compound, (C(3)H(12)N(2))[Hg(C(7)H(3)NO(4))(2)]·2H(2)O, the Hg(II) ion is coordinated by four O and two N atoms of two pyridine-2,6-dicarboxyl-ate (pydc) ligands in a distorted octa-hedral environment. The structure contains two uncoordinated water mol-ecules. In the crystal, N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds and π-π stacking inter-actions 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 = 642.98

Triclinic,

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[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 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

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024366/hy2434sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C3H12N2)[Hg(C7H3NO4)2]·2H2O	Z = 2
Mr = 642.98	F(000) = 624
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0168P)2 + 0.6039P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.002
6084 reflections	Δρmax = 0.86 e Å−3
306 parameters	Δρmin = −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)

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···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

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⋯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) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .