Bis(μ-N,N′-di-3-pyridylpyridine-2,6-dicarboxamide)bis­[dichloridomercury(II)] N,N-dimethyl­formamide disolvate

Huang, L.-H.; Wu, J.

doi:10.1107/S1600536808040269

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages m15-m16

doi:10.1107/S1600536808040269

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Bis(μ-N,N′-di-3-pyridylpyridine-2,6-dicarboxamide)bis[dichloridomercury(II)] N,N-dimethylformamide disolvate

Li-Hua Huang ^a and Jie Wu ^a ^*

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: wujie@zzu.edu.cn

(Received 17 September 2008; accepted 30 November 2008; online 6 December 2008)

The asymmetric unit of the binuclear title complex, [Hg₂Cl₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO, contains one-half of the centrosymmetric molecule and one dimethylformamide solvent molecule. The Hg^II atom is four-coordinated by two N atoms from two ligands and two Cl atoms in a distorted tetrahedral coordination geometry. Intramolecular N—H⋯O hydrogen bonds may be effective in the stabilization of the structure. In the crystal structure, π–π contacts between pyridine rings [centroid-to-centroid distances 3.629 (3) and 3.595 (3) Å] may further stabilize the structure.

Related literature

For general background, see: Ockwig et al. (2005 ); Qin et al. (2003 ); Baer et al. (2002 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Hg₂Cl₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO
M_r = 1327.82
Triclinic, $[P \overline 1]$
a = 7.4947 (15) Å
b = 12.262 (3) Å
c = 13.284 (3) Å
α = 79.79 (3)°
β = 73.74 (3)°
γ = 76.21 (3)°
V = 1130.2 (5) Å³
Z = 1
Mo Kα radiation
μ = 7.08 mm⁻¹
T = 294 (2) K
0.20 × 0.18 × 0.17 mm

Data collection

Rigaku Saturn 724 diffractometer
Absorption correction: numerical (CrystalClear; Rigaku/MSC, 2006 ) T_min = 0.332, T_max = 0.379
12347 measured reflections
4422 independent reflections
3995 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.054
S = 1.03
4422 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Hg1—N5ⁱ	2.295 (3)
Hg1—N1	2.337 (3)
Hg1—Cl1	2.3994 (12)
Hg1—Cl2	2.4249 (14)

N5ⁱ—Hg1—N1	106.50 (11)
N5ⁱ—Hg1—Cl1	117.02 (8)
N1—Hg1—Cl1	108.03 (8)
N5ⁱ—Hg1—Cl2	103.20 (9)
N1—Hg1—Cl2	99.40 (8)
Cl1—Hg1—Cl2	120.60 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3	0.86	2.32	3.090 (4)	149
N2—H2A⋯N3	0.86	2.27	2.692 (2)	110
N4—H4A⋯O3	0.86	2.06	2.870 (4)	156
N4—H4A⋯N3	0.86	2.33	2.714 (3)	107

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040269/hk2534sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040269/hk2534Isup2.hkl

checkCIF report

Comment top

The expansion of the field of metal–organic frameworks (MOFs) of predetermined structure depends on the judicious choice of new linkers and nodes of appropriate coordination algorithms (Ockwig et al., 2005). Rigid polydentate N-donor ligands are typical linkers employed in such a work. N,N'-bis(pyridin-3-yl)-2,6-pyridinedicarboxamide, with a rigid conjugated clamp-like configuration, is a convenient bridging ligand for the syntheses of cyclic complexes (Qin et al., 2003; Baer et al., 2002). In this work, we selected this ligand as linker, to generate the new title coordination complex, and we report herein its crystal structure.

The asymmetric unit of the title compound (Fig. 1) contains one-half molecule and an N,N-dimethylformamide (DMF) molecule, where the bond lengths (Allen et al., 1987) and angles are within normal ranges. The Hg^II atom is four-coordinated by two N atoms from two ligands and two Cl atoms in a distorted tetrahedral coordination geometry (Table 1). The two Hg^II atoms are bridged with two N,N'-bis(pyridin-3-yl)-2,6-pyridinedicarboxamide ligands to form a porous MOF with 28-membered macroring. The pyridine rings A (N1/C1–C5), B (N3/C7–C11) and C (N5/C13–C17) are oriented at dihedral angles of A/B = 3.31 (3)°, A/C = 62.29 (3)° and B/C = 60.76 (3)°. The intramolecular N—H···O hydrogen bonds (Table 2, Fig. 1) may be effective in the stabilization of the structure.

In the crystal structure, the π–π contacts between the pyridine rings, Cg1—Cg2ⁱ and Cg3—Cg3ⁱⁱ [symmetry codes: (i) 2 - x, 1 - y, -z; (ii) -x, 2 - y, 1 - z, where Cg1, Cg2 and Cg3 are centroids of the rings A (N1/C1–C5), B (N3/C7–C11) and C (N5/C13–C17), respectively] may further stabilize the structure, with centroid–centroid distances of 3.629 (3) Å and 3.595 (3) Å.

Related literature top

For general background, see: Ockwig et al. (2005); Qin et al. (2003); Baer et al. (2002). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, the ligand N,N'-bis-(pyridin-3-yl)-2,6-pyridinedicarboxamide (0.016 g, 0.05 mmol) in DMF (5 ml) was added dropwise to a solution of HgCl2 (0.028 g, 0.1 mmol) in methanol (5 ml). The precipitate was filtered and the resulting solution was allowed to stand at room temperature in the dark. After one week high quality colorless crystals were obtained and dried in air.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. The asymmetric unit of the title molecule, with the atom-numbering scheme. Hydrogen bonds are shown as dashed lines.

Bis(µ-N,N'-di-3-pyridylpyridine-2,6- dicarboxamide)bis[dichloridomercury(II)] N,N-dimethylformamide disolvate top

Crystal data top

[Hg₂Cl₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO	Z = 1
M_r = 1327.82	F(000) = 640
Triclinic, P1	D_x = 1.951 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4947 (15) Å	Cell parameters from 3289 reflections
b = 12.262 (3) Å	θ = 2.9–26.0°
c = 13.284 (3) Å	µ = 7.08 mm⁻¹
α = 79.79 (3)°	T = 294 K
β = 73.74 (3)°	Prism, colourless
γ = 76.21 (3)°	0.20 × 0.18 × 0.17 mm
V = 1130.2 (5) Å³

Data collection top

Rigaku Saturn 724 diffractometer	4422 independent reflections
Radiation source: fine-focus sealed tube	3995 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 28.5714 pixels mm^-1	θ_max = 26.0°, θ_min = 2.9°
dtprofit.ref scans	h = −9→9
Absorption correction: numerical (CrystalClear; Rigaku/MSC, 2006)	k = −15→15
T_min = 0.332, T_max = 0.379	l = −16→16
12347 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0195P)² + 0.7349P] where P = (F_o² + 2F_c²)/3
4422 reflections	(Δ/σ)_max = 0.002
291 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Hg₂Cl₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO	γ = 76.21 (3)°
M_r = 1327.82	V = 1130.2 (5) Å³
Triclinic, P1	Z = 1
a = 7.4947 (15) Å	Mo Kα radiation
b = 12.262 (3) Å	µ = 7.08 mm⁻¹
c = 13.284 (3) Å	T = 294 K
α = 79.79 (3)°	0.20 × 0.18 × 0.17 mm
β = 73.74 (3)°

Data collection top

Rigaku Saturn 724 diffractometer	4422 independent reflections
Absorption correction: numerical (CrystalClear; Rigaku/MSC, 2006)	3995 reflections with I > 2σ(I)
T_min = 0.332, T_max = 0.379	R_int = 0.030
12347 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.054	H-atom parameters constrained
S = 1.03	Δρ_max = 0.65 e Å⁻³
4422 reflections	Δρ_min = −0.83 e Å⁻³
291 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	0.47943 (3)	0.144664 (13)	0.675659 (12)	0.04821 (7)
Cl1	0.39934 (16)	−0.03890 (9)	0.72493 (9)	0.0566 (3)
Cl2	0.26095 (18)	0.30392 (9)	0.61184 (9)	0.0611 (3)
O1	0.2543 (5)	0.4774 (3)	1.1235 (2)	0.0738 (10)
O2	−0.1219 (4)	0.9357 (2)	0.7985 (2)	0.0511 (7)
O3	0.3641 (4)	0.5771 (2)	0.7182 (2)	0.0546 (8)
N1	0.4906 (4)	0.2103 (2)	0.8281 (2)	0.0358 (7)
N2	0.2824 (4)	0.4689 (2)	0.9507 (2)	0.0337 (7)
H2A	0.2584	0.5087	0.8941	0.040*
N3	0.1061 (4)	0.6871 (2)	0.9285 (2)	0.0316 (7)
N4	0.0775 (4)	0.7801 (2)	0.7310 (2)	0.0352 (7)
H4A	0.1452	0.7151	0.7459	0.042*
N5	0.2361 (4)	0.8435 (2)	0.4443 (2)	0.0387 (7)
N6	0.6833 (5)	0.5377 (3)	0.6475 (2)	0.0417 (8)
C1	0.5503 (5)	0.1381 (3)	0.9066 (3)	0.0387 (9)
H7	0.6118	0.0645	0.8944	0.046*
C2	0.5222 (5)	0.1712 (3)	1.0037 (3)	0.0401 (9)
H8	0.5634	0.1198	1.0569	0.048*
C3	0.4326 (5)	0.2808 (3)	1.0236 (3)	0.0388 (9)
H9	0.4124	0.3036	1.0897	0.047*
C4	0.3738 (5)	0.3557 (3)	0.9418 (3)	0.0313 (8)
C5	0.4047 (5)	0.3161 (3)	0.8456 (3)	0.0323 (8)
H11	0.3639	0.3654	0.7911	0.039*
C6	0.2281 (5)	0.5222 (3)	1.0382 (3)	0.0385 (9)
C7	0.1299 (5)	0.6438 (3)	1.0247 (3)	0.0315 (8)
C8	0.0694 (5)	0.7050 (3)	1.1103 (3)	0.0419 (9)
H14	0.0886	0.6715	1.1759	0.050*
C9	−0.0202 (5)	0.8169 (3)	1.0963 (3)	0.0432 (9)
H15	−0.0601	0.8607	1.1519	0.052*
C10	−0.0493 (5)	0.8622 (3)	0.9980 (3)	0.0384 (9)
H16	−0.1121	0.9367	0.9867	0.046*
C11	0.0159 (5)	0.7954 (3)	0.9168 (3)	0.0323 (8)
C12	−0.0168 (5)	0.8443 (3)	0.8101 (3)	0.0346 (8)
C13	0.0691 (5)	0.8157 (3)	0.6251 (3)	0.0324 (8)
C14	−0.1022 (5)	0.8551 (3)	0.5975 (3)	0.0397 (9)
H20	−0.2165	0.8604	0.6488	0.048*
C15	−0.0995 (6)	0.8861 (3)	0.4925 (3)	0.0437 (10)
H21	−0.2127	0.9115	0.4720	0.052*
C16	0.0711 (6)	0.8796 (3)	0.4179 (3)	0.0424 (10)
H22	0.0713	0.9010	0.3471	0.051*
C17	0.2348 (5)	0.8112 (3)	0.5462 (3)	0.0341 (8)
H23	0.3500	0.7847	0.5645	0.041*
C18	0.8658 (6)	0.5671 (4)	0.6339 (4)	0.0574 (12)
H24A	0.9104	0.5982	0.5620	0.086*
H24B	0.9552	0.5005	0.6504	0.086*
H24C	0.8526	0.6220	0.6802	0.086*
C19	0.6793 (7)	0.4444 (4)	0.5953 (4)	0.0645 (13)
H25A	0.5525	0.4308	0.6137	0.097*
H25B	0.7630	0.3778	0.6174	0.097*
H25C	0.7196	0.4629	0.5202	0.097*
C20	0.5254 (6)	0.5959 (3)	0.7025 (3)	0.0470 (10)
H26	0.5363	0.6565	0.7322	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.06800 (12)	0.04056 (10)	0.03301 (9)	−0.01143 (8)	−0.00684 (7)	−0.00492 (7)
Cl1	0.0584 (7)	0.0423 (6)	0.0694 (7)	−0.0179 (5)	−0.0136 (6)	−0.0004 (5)
Cl2	0.0773 (8)	0.0504 (6)	0.0618 (7)	−0.0063 (6)	−0.0364 (6)	−0.0009 (5)
O1	0.125 (3)	0.0519 (19)	0.0363 (17)	0.0185 (19)	−0.0330 (18)	−0.0114 (14)
O2	0.0582 (18)	0.0368 (15)	0.0444 (16)	0.0123 (14)	−0.0092 (14)	−0.0039 (13)
O3	0.0463 (18)	0.0508 (18)	0.0482 (17)	0.0070 (14)	0.0008 (14)	−0.0013 (14)
N1	0.0415 (18)	0.0313 (16)	0.0329 (16)	−0.0063 (14)	−0.0069 (14)	−0.0047 (13)
N2	0.0470 (18)	0.0270 (15)	0.0231 (15)	0.0000 (13)	−0.0109 (13)	0.0006 (12)
N3	0.0299 (15)	0.0311 (16)	0.0310 (16)	−0.0052 (13)	−0.0035 (13)	−0.0043 (13)
N4	0.0411 (18)	0.0278 (15)	0.0287 (16)	0.0016 (13)	−0.0053 (13)	−0.0002 (13)
N5	0.050 (2)	0.0323 (16)	0.0319 (17)	−0.0067 (15)	−0.0090 (15)	−0.0024 (14)
N6	0.050 (2)	0.0349 (17)	0.0342 (17)	−0.0052 (15)	−0.0043 (15)	−0.0021 (14)
C1	0.039 (2)	0.0321 (19)	0.040 (2)	−0.0018 (16)	−0.0055 (17)	−0.0050 (17)
C2	0.044 (2)	0.036 (2)	0.037 (2)	−0.0031 (17)	−0.0159 (18)	0.0055 (17)
C3	0.050 (2)	0.036 (2)	0.031 (2)	−0.0041 (18)	−0.0150 (18)	−0.0041 (16)
C4	0.0338 (19)	0.0305 (18)	0.0276 (18)	−0.0051 (15)	−0.0075 (15)	−0.0006 (15)
C5	0.042 (2)	0.0294 (18)	0.0243 (18)	−0.0056 (16)	−0.0101 (15)	0.0007 (15)
C6	0.044 (2)	0.041 (2)	0.029 (2)	−0.0039 (18)	−0.0095 (17)	−0.0072 (17)
C7	0.0316 (19)	0.0341 (19)	0.0273 (18)	−0.0065 (15)	−0.0045 (15)	−0.0045 (15)
C8	0.045 (2)	0.051 (2)	0.029 (2)	−0.0106 (19)	−0.0050 (17)	−0.0096 (18)
C9	0.048 (2)	0.044 (2)	0.037 (2)	−0.0104 (19)	0.0008 (18)	−0.0206 (18)
C10	0.037 (2)	0.034 (2)	0.043 (2)	−0.0042 (16)	−0.0050 (17)	−0.0120 (17)
C11	0.0293 (18)	0.0325 (19)	0.0319 (19)	−0.0071 (15)	−0.0004 (15)	−0.0063 (16)
C12	0.033 (2)	0.032 (2)	0.035 (2)	−0.0030 (16)	−0.0058 (16)	−0.0025 (16)
C13	0.039 (2)	0.0212 (17)	0.035 (2)	−0.0014 (15)	−0.0110 (16)	−0.0010 (15)
C14	0.039 (2)	0.0318 (19)	0.048 (2)	−0.0065 (17)	−0.0102 (18)	−0.0053 (17)
C15	0.051 (2)	0.0291 (19)	0.059 (3)	−0.0043 (18)	−0.030 (2)	−0.0036 (19)
C16	0.064 (3)	0.029 (2)	0.040 (2)	−0.0092 (19)	−0.024 (2)	−0.0007 (17)
C17	0.039 (2)	0.0298 (18)	0.0311 (19)	−0.0017 (16)	−0.0099 (16)	−0.0016 (15)
C18	0.058 (3)	0.059 (3)	0.054 (3)	−0.019 (2)	−0.013 (2)	0.005 (2)
C19	0.058 (3)	0.053 (3)	0.074 (3)	−0.016 (2)	0.010 (2)	−0.024 (2)
C20	0.064 (3)	0.036 (2)	0.033 (2)	0.003 (2)	−0.012 (2)	−0.0016 (17)

Geometric parameters (Å, º) top

Hg1—N5ⁱ	2.295 (3)	C3—H9	0.9300
Hg1—N1	2.337 (3)	C4—C5	1.387 (5)
Hg1—Cl1	2.3994 (12)	C5—H11	0.9300
Hg1—Cl2	2.4249 (14)	C6—C7	1.501 (5)
O1—C6	1.215 (4)	C7—C8	1.383 (5)
O2—C12	1.219 (4)	C8—C9	1.381 (5)
O3—C20	1.238 (5)	C8—H14	0.9300
N1—C5	1.333 (4)	C9—C10	1.381 (5)
N1—C1	1.348 (5)	C9—H15	0.9300
N2—C6	1.349 (4)	C10—C11	1.378 (5)
N2—C4	1.404 (4)	C10—H16	0.9300
N2—H2A	0.8600	C11—C12	1.501 (5)
N3—C7	1.338 (4)	C13—C17	1.379 (5)
N3—C11	1.343 (4)	C13—C14	1.386 (5)
N4—C12	1.354 (4)	C14—C15	1.374 (5)
N4—C13	1.412 (4)	C14—H20	0.9300
N4—H4A	0.8600	C15—C16	1.377 (6)
N5—C16	1.332 (5)	C15—H21	0.9300
N5—C17	1.340 (4)	C16—H22	0.9300
N5—Hg1ⁱ	2.295 (3)	C17—H23	0.9300
N6—C20	1.320 (5)	C18—H24A	0.9600
N6—C19	1.449 (5)	C18—H24B	0.9600
N6—C18	1.451 (5)	C18—H24C	0.9600
C1—C2	1.365 (5)	C19—H25A	0.9600
C1—H7	0.9300	C19—H25B	0.9600
C2—C3	1.387 (5)	C19—H25C	0.9600
C2—H8	0.9300	C20—H26	0.9300
C3—C4	1.392 (5)

N5ⁱ—Hg1—N1	106.50 (11)	C9—C8—H14	120.7
N5ⁱ—Hg1—Cl1	117.02 (8)	C7—C8—H14	120.7
N1—Hg1—Cl1	108.03 (8)	C10—C9—C8	118.6 (4)
N5ⁱ—Hg1—Cl2	103.20 (9)	C10—C9—H15	120.7
N1—Hg1—Cl2	99.40 (8)	C8—C9—H15	120.7
Cl1—Hg1—Cl2	120.60 (4)	C11—C10—C9	119.1 (4)
C5—N1—C1	119.2 (3)	C11—C10—H16	120.5
C5—N1—Hg1	118.8 (2)	C9—C10—H16	120.5
C1—N1—Hg1	120.8 (2)	N3—C11—C10	123.2 (3)
C6—N2—C4	127.2 (3)	N3—C11—C12	117.7 (3)
C6—N2—H2A	116.4	C10—C11—C12	119.1 (3)
C4—N2—H2A	116.4	O2—C12—N4	124.1 (3)
C7—N3—C11	117.0 (3)	O2—C12—C11	120.6 (3)
C12—N4—C13	122.6 (3)	N4—C12—C11	115.3 (3)
C12—N4—H4A	118.7	C17—C13—C14	118.5 (3)
C13—N4—H4A	118.7	C17—C13—N4	119.7 (3)
C16—N5—C17	118.8 (3)	C14—C13—N4	121.8 (3)
C16—N5—Hg1ⁱ	122.1 (2)	C15—C14—C13	118.6 (4)
C17—N5—Hg1ⁱ	118.7 (2)	C15—C14—H20	120.7
C20—N6—C19	120.9 (4)	C13—C14—H20	120.7
C20—N6—C18	121.5 (4)	C14—C15—C16	119.9 (4)
C19—N6—C18	117.6 (3)	C14—C15—H21	120.1
N1—C1—C2	121.1 (3)	C16—C15—H21	120.1
N1—C1—H7	119.4	N5—C16—C15	121.8 (4)
C2—C1—H7	119.4	N5—C16—H22	119.1
C1—C2—C3	120.6 (3)	C15—C16—H22	119.1
C1—C2—H8	119.7	N5—C17—C13	122.5 (3)
C3—C2—H8	119.7	N5—C17—H23	118.8
C2—C3—C4	118.1 (3)	C13—C17—H23	118.8
C2—C3—H9	120.9	N6—C18—H24A	109.5
C4—C3—H9	120.9	N6—C18—H24B	109.5
C5—C4—C3	118.3 (3)	H24A—C18—H24B	109.5
C5—C4—N2	117.5 (3)	N6—C18—H24C	109.5
C3—C4—N2	124.2 (3)	H24A—C18—H24C	109.5
N1—C5—C4	122.6 (3)	H24B—C18—H24C	109.5
N1—C5—H11	118.7	N6—C19—H25A	109.5
C4—C5—H11	118.7	N6—C19—H25B	109.5
O1—C6—N2	123.9 (4)	H25A—C19—H25B	109.5
O1—C6—C7	120.5 (3)	N6—C19—H25C	109.5
N2—C6—C7	115.5 (3)	H25A—C19—H25C	109.5
N3—C7—C8	123.5 (3)	H25B—C19—H25C	109.5
N3—C7—C6	117.1 (3)	O3—C20—N6	126.0 (4)
C8—C7—C6	119.5 (3)	O3—C20—H26	117.0
C9—C8—C7	118.7 (4)	N6—C20—H26	117.0

N5ⁱ—Hg1—N1—C5	99.7 (3)	C6—C7—C8—C9	179.8 (3)
Cl1—Hg1—N1—C5	−133.8 (2)	C7—C8—C9—C10	1.4 (6)
Cl2—Hg1—N1—C5	−7.2 (3)	C8—C9—C10—C11	−1.6 (6)
N5ⁱ—Hg1—N1—C1	−92.7 (3)	C7—N3—C11—C10	0.7 (5)
Cl1—Hg1—N1—C1	33.8 (3)	C7—N3—C11—C12	−178.3 (3)
Cl2—Hg1—N1—C1	160.5 (3)	C9—C10—C11—N3	0.6 (6)
C5—N1—C1—C2	0.9 (6)	C9—C10—C11—C12	179.6 (3)
Hg1—N1—C1—C2	−166.7 (3)	C13—N4—C12—O2	2.8 (6)
N1—C1—C2—C3	−0.7 (6)	C13—N4—C12—C11	−177.2 (3)
C1—C2—C3—C4	−0.4 (6)	N3—C11—C12—O2	168.8 (3)
C2—C3—C4—C5	1.2 (5)	C10—C11—C12—O2	−10.3 (5)
C2—C3—C4—N2	−179.7 (3)	N3—C11—C12—N4	−11.2 (5)
C6—N2—C4—C5	175.5 (4)	C10—C11—C12—N4	169.7 (3)
C6—N2—C4—C3	−3.6 (6)	C12—N4—C13—C17	129.3 (4)
C1—N1—C5—C4	0.0 (5)	C12—N4—C13—C14	−51.0 (5)
Hg1—N1—C5—C4	167.8 (3)	C17—C13—C14—C15	1.0 (5)
C3—C4—C5—N1	−1.0 (5)	N4—C13—C14—C15	−178.7 (3)
N2—C4—C5—N1	179.8 (3)	C13—C14—C15—C16	−1.2 (5)
C4—N2—C6—O1	0.8 (7)	C17—N5—C16—C15	1.1 (5)
C4—N2—C6—C7	−179.0 (3)	Hg1ⁱ—N5—C16—C15	−171.3 (3)
C11—N3—C7—C8	−0.9 (5)	C14—C15—C16—N5	0.1 (6)
C11—N3—C7—C6	179.1 (3)	C16—N5—C17—C13	−1.2 (5)
O1—C6—C7—N3	−179.9 (4)	Hg1ⁱ—N5—C17—C13	171.4 (3)
N2—C6—C7—N3	0.0 (5)	C14—C13—C17—N5	0.1 (5)
O1—C6—C7—C8	0.1 (6)	N4—C13—C17—N5	179.9 (3)
N2—C6—C7—C8	−180.0 (3)	C19—N6—C20—O3	2.2 (6)
N3—C7—C8—C9	−0.1 (6)	C18—N6—C20—O3	179.9 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.86	2.32	3.090 (4)	149
N2—H2A···N3	0.86	2.27	2.692 (2)	110
N4—H4A···O3	0.86	2.06	2.870 (4)	156
N4—H4A···N3	0.86	2.33	2.714 (3)	107

Experimental details

Crystal data
Chemical formula	[Hg₂Cl₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO
M_r	1327.82
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.4947 (15), 12.262 (3), 13.284 (3)
α, β, γ (°)	79.79 (3), 73.74 (3), 76.21 (3)
V (Å³)	1130.2 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	7.08
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Rigaku Saturn 724 diffractometer
Absorption correction	Numerical (CrystalClear; Rigaku/MSC, 2006)
T_min, T_max	0.332, 0.379
No. of measured, independent and observed [I > 2σ(I)] reflections	12347, 4422, 3995
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.054, 1.03
No. of reflections	4422
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.83

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Hg1—N5ⁱ	2.295 (3)	Hg1—Cl1	2.3994 (12)
Hg1—N1	2.337 (3)	Hg1—Cl2	2.4249 (14)

N5ⁱ—Hg1—N1	106.50 (11)	N5ⁱ—Hg1—Cl2	103.20 (9)
N5ⁱ—Hg1—Cl1	117.02 (8)	N1—Hg1—Cl2	99.40 (8)
N1—Hg1—Cl1	108.03 (8)	Cl1—Hg1—Cl2	120.60 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.86	2.32	3.090 (4)	149
N2—H2A···N3	0.86	2.27	2.692 (2)	110
N4—H4A···O3	0.86	2.06	2.870 (4)	156
N4—H4A···N3	0.86	2.33	2.714 (3)	107

Acknowledgements

The authors thank Professor Hou Hong-Wei of Zhengzhou University for his help.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Baer, A. J., Koivisto, B. D., Taylor, N. J., Hanan, G. S., Nierengarten, H. & Dorsselaer, A. V. (2002). Inorg. Chem. 41, 4987–4989. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ockwig, N. W., Delgado-Friedrichs, O., O'Keeffe, M. & Yaghi, O. M. (2005). Acc. Chem. Res. 38, 176–182. Web of Science CrossRef PubMed CAS Google Scholar
Qin, Z.-Q., Jennings, M. C. & Puddephatt, R. J. (2003). Inorg. Chem. 42, 1956–1965. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 1| January 2009| Pages m15-m16

doi:10.1107/S1600536808040269

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

Bis(μ-N,N′-di-3-pyridylpyridine-2,6-dicarboxamide)bis­­[di­chloridomercury(II)] N,N-di­methyl­formamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(μ-N,N′-di-3-pyridylpyridine-2,6-dicarboxamide)bis[dichloridomercury(II)] N,N-dimethylformamide disolvate