catena-Poly[[[diiodidomercury(II)]-μ-N,N'-di-3-pyridylpyridine-2,6-dicarboxamide] dimethyl-formamide solvate].

In the title complex, {[HgI(2)(C(17)H(13)N(5)O(2))]·C(3)H(7)NO}(n), the Hg atom is coordinated by two I atoms and two N atoms from two different ligands in a distorted tetra-hedral environment. Hg atoms are bridged by N,N'-di-3-pyridylpyridine-2,6-dicarboxamide ligands, forming a helical chain running along the a axis.

Related literature

For binuclear complexes of N,N′-bis­(pyridin-3-yl)-2,6-pyridine­dicarboxamide, see: Baer et al. (2002 ▶); Huang & Wu (2008 ▶); Qin et al. (2003 ▶).

Experimental

Crystal data

[HgI2(C17H13N5O2)]·C3H7NO

M = 846.81

Orthorhombic,

a = 21.295 (4) Å

b = 9.7177 (19) Å

c = 24.440 (5) Å

V = 5057.5 (17) Å3

Z = 8

Mo Kα radiation

μ = 8.56 mm−1

T = 293 (2) K

0.20 × 0.18 × 0.08 mm

Data collection

Rigaku Saturn724 diffractometer

Absorption correction: numerical (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.279, T max = 0.547

48014 measured reflections

4447 independent reflections

4250 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.119

S = 1.31

4447 reflections

291 parameters

H-atom parameters constrained

Δρmax = 1.21 e Å−3

Δρmin = −0.92 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036581/hg2428sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036581/hg2428Isup2.hkl

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

[HgI2(C17H13N5O2)]·C3H7NO	F000 = 3136
Mr = 846.81	Dx = 2.224 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8721 reflections
a = 21.295 (4) Å	θ = 3.2–26.0º
b = 9.7177 (19) Å	µ = 8.56 mm−1
c = 24.440 (5) Å	T = 293 (2) K
V = 5057.5 (17) Å3	Prism, colorless
Z = 8	0.20 × 0.18 × 0.08 mm

Saturn724 diffractometer	4447 independent reflections
Radiation source: fine-focus sealed tube	4250 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.073
Detector resolution: 28.5714 pixels mm-1	θmax = 25.0º
T = 291(2) K	θmin = 3.3º
dtprofit.ref scans	h = −25→25
Absorption correction: Numerical(CrystalClear; Rigaku/MSC, 2006)	k = −11→11
Tmin = 0.279, Tmax = 0.548	l = −29→29
48014 measured reflections

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)] = 0.062	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0319P)2 + 27.0127P] where P = (Fo2 + 2Fc2)/3
S = 1.31	(Δ/σ)max = 0.001
4447 reflections	Δρmax = 1.21 e Å−3
291 parameters	Δρmin = −0.92 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.374277 (19)	0.12855 (4)	0.670365 (18)	0.05404 (16)
I1	0.34375 (4)	−0.02626 (8)	0.58368 (3)	0.0644 (2)
I2	0.44953 (4)	0.13315 (9)	0.75677 (3)	0.0709 (3)
O1	0.8018 (3)	0.4961 (8)	0.6739 (3)	0.069 (2)
O2	0.5375 (3)	0.7089 (8)	0.5249 (3)	0.065 (2)
O3	0.5923 (3)	0.2832 (8)	0.6383 (3)	0.063 (2)
N1	0.7739 (4)	0.2015 (9)	0.7954 (4)	0.053 (2)
N2	0.7026 (3)	0.4172 (9)	0.6896 (3)	0.050 (2)
H2	0.6649	0.4223	0.6772	0.060*
N3	0.6581 (3)	0.5688 (8)	0.6070 (3)	0.0432 (18)
N4	0.5345 (3)	0.5356 (8)	0.5879 (3)	0.0450 (19)
H4	0.5581	0.4874	0.6091	0.054*
N5	0.3933 (4)	0.3479 (7)	0.6244 (4)	0.047 (2)
N6	0.5553 (4)	0.0721 (9)	0.6163 (4)	0.053 (2)
C1	0.7230 (5)	0.1535 (11)	0.8191 (5)	0.059 (3)
H1	0.7274	0.0923	0.8481	0.070*
C2	0.6634 (5)	0.1903 (12)	0.8027 (4)	0.056 (3)
H2A	0.6281	0.1551	0.8202	0.067*
C3	0.6576 (4)	0.2814 (10)	0.7594 (4)	0.048 (2)
H5	0.6181	0.3091	0.7473	0.057*
C4	0.7112 (4)	0.3301 (10)	0.7344 (4)	0.044 (2)
C5	0.7690 (4)	0.2899 (10)	0.7538 (4)	0.049 (2)
H3	0.8053	0.3247	0.7377	0.059*
C6	0.7461 (5)	0.4951 (11)	0.6630 (4)	0.051 (3)
C7	0.7196 (4)	0.5800 (10)	0.6170 (4)	0.048 (2)
C8	0.7579 (5)	0.6690 (12)	0.5882 (5)	0.061 (3)
H8	0.8005	0.6756	0.5962	0.073*
C9	0.7315 (5)	0.7476 (13)	0.5473 (5)	0.067 (3)
H9	0.7564	0.8069	0.5268	0.081*
C10	0.6680 (5)	0.7383 (11)	0.5367 (4)	0.057 (3)
H10	0.6493	0.7922	0.5099	0.068*
C11	0.6331 (4)	0.6463 (10)	0.5674 (4)	0.044 (2)
C12	0.5642 (5)	0.6341 (10)	0.5573 (4)	0.048 (2)
C13	0.4705 (4)	0.5039 (9)	0.5891 (4)	0.042 (2)
C14	0.4245 (5)	0.5696 (11)	0.5587 (5)	0.054 (3)
H14	0.4345	0.6445	0.5367	0.065*
C15	0.3633 (5)	0.5216 (12)	0.5618 (5)	0.063 (3)
H15	0.3314	0.5648	0.5422	0.075*
C16	0.3505 (5)	0.4110 (12)	0.5937 (5)	0.059 (3)
H16	0.3096	0.3774	0.5942	0.071*
C17	0.4519 (5)	0.3943 (10)	0.6222 (4)	0.050 (3)
H17	0.4820	0.3516	0.6439	0.061*
C18	0.5424 (7)	0.1046 (15)	0.5597 (5)	0.091 (4)
H18A	0.4990	0.0863	0.5519	0.136*
H18B	0.5683	0.0489	0.5365	0.136*
H18C	0.5511	0.2001	0.5532	0.136*
C19	0.5445 (6)	−0.0682 (12)	0.6371 (6)	0.081 (4)
H19A	0.5770	−0.1281	0.6239	0.121*
H19B	0.5045	−0.1008	0.6245	0.121*
H19C	0.5450	−0.0672	0.6763	0.121*
C20	0.5801 (4)	0.1635 (10)	0.6498 (4)	0.047 (2)
H20	0.5891	0.1345	0.6852	0.057*

	U11	U22	U33	U12	U13	U23
Hg1	0.0468 (3)	0.0576 (3)	0.0577 (3)	−0.00017 (19)	0.00731 (19)	−0.0057 (2)
I1	0.0753 (5)	0.0618 (5)	0.0562 (5)	−0.0038 (4)	0.0088 (4)	−0.0071 (4)
I2	0.0654 (5)	0.0874 (6)	0.0599 (5)	−0.0060 (4)	−0.0026 (4)	−0.0047 (4)
O1	0.039 (4)	0.085 (6)	0.083 (6)	−0.017 (4)	−0.016 (4)	0.029 (4)
O2	0.068 (5)	0.063 (5)	0.066 (5)	−0.002 (4)	−0.015 (4)	0.024 (4)
O3	0.047 (4)	0.058 (5)	0.084 (6)	−0.006 (4)	−0.013 (4)	0.012 (4)
N1	0.045 (5)	0.055 (5)	0.058 (6)	−0.002 (4)	−0.011 (4)	0.010 (4)
N2	0.033 (4)	0.057 (5)	0.060 (5)	−0.003 (4)	−0.007 (4)	0.017 (4)
N3	0.040 (4)	0.044 (4)	0.046 (5)	−0.005 (4)	0.000 (4)	0.003 (4)
N4	0.044 (4)	0.051 (5)	0.040 (5)	0.000 (4)	−0.007 (4)	0.013 (4)
N5	0.038 (4)	0.037 (4)	0.066 (6)	0.000 (3)	−0.007 (4)	0.003 (4)
N6	0.049 (5)	0.055 (5)	0.054 (6)	0.008 (4)	−0.005 (4)	−0.003 (4)
C1	0.044 (6)	0.062 (7)	0.070 (8)	−0.005 (5)	−0.001 (5)	0.017 (6)
C2	0.045 (6)	0.076 (7)	0.046 (6)	−0.010 (5)	0.013 (5)	0.010 (6)
C3	0.029 (5)	0.055 (6)	0.060 (7)	−0.003 (4)	−0.003 (4)	0.004 (5)
C4	0.042 (5)	0.044 (5)	0.045 (6)	0.001 (4)	−0.005 (4)	−0.002 (4)
C5	0.036 (5)	0.054 (6)	0.058 (6)	0.000 (5)	−0.007 (5)	0.006 (5)
C6	0.042 (6)	0.059 (6)	0.051 (6)	−0.007 (5)	0.001 (5)	0.011 (5)
C7	0.035 (5)	0.055 (6)	0.055 (6)	−0.013 (5)	0.003 (4)	0.003 (5)
C8	0.044 (6)	0.076 (7)	0.062 (7)	−0.020 (5)	−0.002 (5)	0.014 (6)
C9	0.062 (7)	0.079 (8)	0.061 (7)	−0.022 (6)	0.006 (6)	0.022 (6)
C10	0.069 (7)	0.053 (6)	0.048 (6)	−0.013 (5)	−0.009 (5)	0.013 (5)
C11	0.053 (6)	0.049 (6)	0.030 (5)	−0.005 (5)	0.000 (4)	0.008 (4)
C12	0.059 (6)	0.048 (6)	0.037 (6)	0.003 (5)	−0.005 (5)	0.005 (5)
C13	0.035 (5)	0.047 (5)	0.043 (5)	0.008 (4)	−0.008 (4)	−0.004 (4)
C14	0.047 (6)	0.049 (6)	0.067 (7)	0.007 (5)	−0.003 (5)	0.006 (5)
C15	0.060 (7)	0.065 (7)	0.063 (8)	0.009 (6)	−0.020 (6)	0.008 (6)
C16	0.039 (5)	0.065 (7)	0.073 (8)	0.004 (5)	−0.007 (5)	−0.003 (6)
C17	0.045 (6)	0.047 (6)	0.060 (7)	0.005 (5)	−0.007 (5)	0.009 (5)
C18	0.110 (11)	0.111 (12)	0.052 (8)	0.000 (9)	−0.008 (7)	−0.003 (8)
C19	0.081 (9)	0.050 (7)	0.111 (11)	0.002 (6)	0.006 (8)	−0.011 (7)
C20	0.039 (5)	0.046 (6)	0.057 (6)	0.009 (5)	−0.005 (5)	0.003 (5)

Hg1—N1i	2.403 (8)	C3—H5	0.9300
Hg1—N5	2.444 (8)	C4—C5	1.377 (12)
Hg1—I2	2.6514 (10)	C5—H3	0.9300
Hg1—I1	2.6785 (10)	C6—C7	1.504 (14)
O1—C6	1.215 (12)	C7—C8	1.381 (14)
O2—C12	1.217 (11)	C8—C9	1.380 (15)
O3—C20	1.225 (11)	C8—H8	0.9300
N1—C1	1.314 (13)	C9—C10	1.378 (14)
N1—C5	1.335 (12)	C9—H9	0.9300
N1—Hg1ii	2.403 (8)	C10—C11	1.384 (13)
N2—C6	1.362 (12)	C10—H10	0.9300
N2—C4	1.395 (12)	C11—C12	1.492 (13)
N2—H2	0.8600	C13—C14	1.387 (13)
N3—C7	1.336 (11)	C13—C17	1.395 (13)
N3—C11	1.337 (11)	C14—C15	1.387 (14)
N4—C12	1.370 (12)	C14—H14	0.9300
N4—C13	1.396 (11)	C15—C16	1.356 (16)
N4—H4	0.8600	C15—H15	0.9300
N5—C17	1.327 (12)	C16—H16	0.9300
N5—C16	1.330 (13)	C17—H17	0.9300
N6—C20	1.318 (13)	C18—H18A	0.9600
N6—C18	1.445 (15)	C18—H18B	0.9600
N6—C19	1.473 (14)	C18—H18C	0.9600
C1—C2	1.379 (14)	C19—H19A	0.9600
C1—H1	0.9300	C19—H19B	0.9600
C2—C3	1.386 (14)	C19—H19C	0.9600
C2—H2A	0.9300	C20—H20	0.9300
C3—C4	1.378 (13)
N1i—Hg1—N5	92.9 (3)	C9—C8—H8	120.8
N1i—Hg1—I2	104.8 (2)	C7—C8—H8	120.8
N5—Hg1—I2	104.57 (19)	C10—C9—C8	119.9 (10)
N1i—Hg1—I1	103.0 (2)	C10—C9—H9	120.0
N5—Hg1—I1	99.6 (2)	C8—C9—H9	120.0
I2—Hg1—I1	141.83 (3)	C9—C10—C11	117.9 (10)
C1—N1—C5	120.1 (9)	C9—C10—H10	121.0
C1—N1—Hg1ii	118.3 (7)	C11—C10—H10	121.0
C5—N1—Hg1ii	121.6 (6)	N3—C11—C10	122.8 (9)
C6—N2—C4	128.5 (8)	N3—C11—C12	117.9 (8)
C6—N2—H2	115.7	C10—C11—C12	119.3 (9)
C4—N2—H2	115.7	O2—C12—N4	123.9 (9)
C7—N3—C11	118.5 (8)	O2—C12—C11	121.3 (9)
C12—N4—C13	128.1 (8)	N4—C12—C11	114.8 (8)
C12—N4—H4	116.0	C14—C13—C17	117.5 (9)
C13—N4—H4	116.0	C14—C13—N4	125.2 (9)
C17—N5—C16	117.8 (9)	C17—C13—N4	117.3 (8)
C17—N5—Hg1	118.0 (6)	C13—C14—C15	118.7 (10)
C16—N5—Hg1	123.2 (7)	C13—C14—H14	120.6
C20—N6—C18	121.6 (10)	C15—C14—H14	120.6
C20—N6—C19	118.2 (10)	C16—C15—C14	119.2 (10)
C18—N6—C19	120.1 (10)	C16—C15—H15	120.4
N1—C1—C2	122.6 (10)	C14—C15—H15	120.4
N1—C1—H1	118.7	N5—C16—C15	123.5 (10)
C2—C1—H1	118.7	N5—C16—H16	118.3
C1—C2—C3	118.1 (9)	C15—C16—H16	118.3
C1—C2—H2A	121.0	N5—C17—C13	123.3 (9)
C3—C2—H2A	121.0	N5—C17—H17	118.3
C4—C3—C2	119.0 (9)	C13—C17—H17	118.3
C4—C3—H5	120.5	N6—C18—H18A	109.5
C2—C3—H5	120.5	N6—C18—H18B	109.5
C5—C4—C3	119.4 (9)	H18A—C18—H18B	109.5
C5—C4—N2	124.0 (9)	N6—C18—H18C	109.5
C3—C4—N2	116.6 (8)	H18A—C18—H18C	109.5
N1—C5—C4	120.9 (9)	H18B—C18—H18C	109.5
N1—C5—H3	119.5	N6—C19—H19A	109.5
C4—C5—H3	119.5	N6—C19—H19B	109.5
O1—C6—N2	124.3 (9)	H19A—C19—H19B	109.5
O1—C6—C7	121.7 (9)	N6—C19—H19C	109.5
N2—C6—C7	114.0 (8)	H19A—C19—H19C	109.5
N3—C7—C8	122.4 (10)	H19B—C19—H19C	109.5
N3—C7—C6	117.4 (8)	O3—C20—N6	125.7 (10)
C8—C7—C6	120.2 (9)	O3—C20—H20	117.2
C9—C8—C7	118.4 (10)	N6—C20—H20	117.2
N1i—Hg1—N5—C17	145.4 (8)	C6—C7—C8—C9	−178.4 (11)
I2—Hg1—N5—C17	39.3 (8)	C7—C8—C9—C10	1.3 (19)
I1—Hg1—N5—C17	−110.8 (7)	C8—C9—C10—C11	−1.5 (18)
N1i—Hg1—N5—C16	−46.3 (9)	C7—N3—C11—C10	−0.6 (15)
I2—Hg1—N5—C16	−152.4 (8)	C7—N3—C11—C12	−179.1 (9)
I1—Hg1—N5—C16	57.4 (8)	C9—C10—C11—N3	1.2 (16)
C5—N1—C1—C2	0.2 (17)	C9—C10—C11—C12	179.7 (10)
Hg1ii—N1—C1—C2	179.4 (9)	C13—N4—C12—O2	−1.3 (17)
N1—C1—C2—C3	0.2 (17)	C13—N4—C12—C11	177.4 (9)
C1—C2—C3—C4	0.5 (16)	N3—C11—C12—O2	174.3 (10)
C2—C3—C4—C5	−1.5 (15)	C10—C11—C12—O2	−4.3 (15)
C2—C3—C4—N2	177.5 (9)	N3—C11—C12—N4	−4.4 (13)
C6—N2—C4—C5	−11.9 (17)	C10—C11—C12—N4	177.0 (9)
C6—N2—C4—C3	169.2 (10)	C12—N4—C13—C14	−0.5 (16)
C1—N1—C5—C4	−1.2 (15)	C12—N4—C13—C17	177.3 (10)
Hg1ii—N1—C5—C4	179.6 (7)	C17—C13—C14—C15	−1.4 (15)
C3—C4—C5—N1	1.9 (15)	N4—C13—C14—C15	176.4 (10)
N2—C4—C5—N1	−177.1 (9)	C13—C14—C15—C16	−1.0 (17)
C4—N2—C6—O1	2.9 (18)	C17—N5—C16—C15	−1.8 (17)
C4—N2—C6—C7	−178.4 (9)	Hg1—N5—C16—C15	−170.1 (9)
C11—N3—C7—C8	0.3 (15)	C14—C15—C16—N5	2.7 (19)
C11—N3—C7—C6	178.0 (9)	C16—N5—C17—C13	−0.9 (15)
O1—C6—C7—N3	177.9 (10)	Hg1—N5—C17—C13	168.1 (8)
N2—C6—C7—N3	−0.9 (14)	C14—C13—C17—N5	2.4 (15)
O1—C6—C7—C8	−4.3 (17)	N4—C13—C17—N5	−175.6 (9)
N2—C6—C7—C8	176.9 (10)	C18—N6—C20—O3	3.1 (16)
N3—C7—C8—C9	−0.7 (18)	C19—N6—C20—O3	179.3 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O3	0.86	2.23	3.008 (10)	150
N2—H2···O3	0.86	2.26	2.964 (10)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O3	0.86	2.23	3.008 (10)	150
N2—H2⋯O3	0.86	2.26	2.964 (10)	139