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

The asymmetric unit of the binuclear title complex, [Hg(2)Cl(4)(C(17)H(13)N(5)O(2))(2)]·2C(3)H(7)NO, contains one-half of the centrosymmetric mol-ecule and one dimethyl-formamide solvent mol-ecule. The Hg(II) atom is four-coordinated by two N atoms from two ligands and two Cl atoms in a distorted tetra-hedral coordination geometry. Intra-molecular 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 = 1327.82

Triclinic,

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[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.054

S = 1.03

4422 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.83 e Å−3

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.

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

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

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

[Hg2Cl4(C17H13N5O2)2]·2C3H7NO	Z = 1
Mr = 1327.82	F(000) = 640
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0195P)2 + 0.7349P] where P = (Fo2 + 2Fc2)/3
4422 reflections	(Δ/σ)max = 0.002
291 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.83 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .

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