catena-Poly[[[diiodidomercury(II)]-μ-N,N′-di-3-pyridylpyridine-2,6-dicarboxamide] dimethyl­formamide solvate]

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

doi:10.1107/S1600536808036581

catena-Poly[[[diiodidomercury(II)]-μ-N,N′-di-3-pyridylpyridine-2,6-dicarboxamide] dimethylformamide solvate]

In the title complex, {[HgI₂(C₁₇H₁₃N₅O₂)]·C₃H₇NO}_n, the Hg atom is coordinated by two I atoms and two N atoms from two different ligands in a distorted tetrahedral environment. Hg atoms are bridged by N,N′-di-3-pyridylpyridine-2,6-dicarboxamide ligands, forming a helical chain running along the a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808036581/hg2428sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808036581/hg2428Isup2.hkl Contains datablock I

CCDC reference: 712294

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.014 Å
R factor = 0.062
wR factor = 0.119
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT083_ALERT_2_B SHELXL Second Parameter in WGHT unusually Large.      27.00

Alert level C
            Value of measurement temperature given =   293.000
            Value of melting point given =     0.000
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         14
PLAT234_ALERT_4_C Large Hirshfeld Difference Hg1    --  N5      ..       0.14  Ang.
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N6

Alert level G
ABSTM02_ALERT_3_G  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.279     0.548
            Tmin and Tmax expected:      0.196     0.504
            RR =      1.312
            Please check that your absorption correction is appropriate.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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. Rigid, polydentate N-donor ligands are typical linkers employed in such work. The rigid conjugated clamp-like multi-pyridine ligand N,N'-bis(pyridin-3-yl)-2,6-pyridinedicarboxamide, is a convenient bridging ligand for the synthesis of chain complexes. However, the previous work proved that the ligand also can form binuclear complex with 28-number ring (Huang et al.; 2004, Qin et al. 2003; Baer et al. 2002). We think, among the factors that induce the self-assembly processes with this ligand, the rotation of terminal pyridine groups plays a crucial role in deciding between binuclear versus. extended structures of the metal complexes. In this work, we selected this ligand as linker, generating a new helical chain coordination complex, {[HgI₂(C₁₇N₅O₂)](DMF)}_n, (I), which is reported here. In compound (I) each Hg(II) atom is four-coordinated by two N atoms from two ligands and two I atoms in a distorted tetrahedral coordination sphere (Fig. 1). The Hg(II) atoms are bridged with N,N'-bis(pyridin-3-yl)-2,6-pyridinedicarboxamide ligands to form a helical chain running the a axis (Fig. 2).

In the crystal structure, the intermolecular N—H···N hydrogen bonds and the N—H···O hydrogen bonds arising from the DMF and ligand complete the structure.

Related literature top

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

Experimental top

The ligand N,N'-bis(pyridin-3-yl)-2,6-pyridinedicarboxamide (0.05 mmol, 0.016 g) in DMF (5 ml) was added dropwise to a solution of HgI2 (0.1 mmol, 0.036 g) in methanol (3 ml). The precipitate was filtered and the resulting solution was allowed to stand at room temperature in the dark. After one week good quality colorless crystals were obtained from the filtrate 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title complex, showing the labeling of the non-H atoms and 30% probability ellipsolids.
	Fig. 2. A view of the crystal packing along the c axis.

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

Crystal data top

[HgI₂(C₁₇H₁₃N₅O₂)]·C₃H₇NO	F(000) = 3136
M_r = 846.81	D_x = 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 = 3.2–26.0°
b = 9.7177 (19) Å	µ = 8.56 mm⁻¹
c = 24.440 (5) Å	T = 293 K
V = 5057.5 (17) Å³	Prism, colorless
Z = 8	0.20 × 0.18 × 0.08 mm

Data collection top

Saturn724 diffractometer	4447 independent reflections
Radiation source: fine-focus sealed tube	4250 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.0°, θ_min = 3.3°
dtprofit.ref scans	h = −25→25
Absorption correction: numerical (CrystalClear; Rigaku/MSC, 2006)	k = −11→11
T_min = 0.279, T_max = 0.548	l = −29→29
48014 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.31	w = 1/[σ²(F_o²) + (0.0319P)² + 27.0127P] where P = (F_o² + 2F_c²)/3
4447 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 1.21 e Å⁻³
0 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

[HgI₂(C₁₇H₁₃N₅O₂)]·C₃H₇NO	V = 5057.5 (17) Å³
M_r = 846.81	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 21.295 (4) Å	µ = 8.56 mm⁻¹
b = 9.7177 (19) Å	T = 293 K
c = 24.440 (5) Å	0.20 × 0.18 × 0.08 mm

Data collection top

Saturn724 diffractometer	4447 independent reflections
Absorption correction: numerical (CrystalClear; Rigaku/MSC, 2006)	4250 reflections with I > 2σ(I)
T_min = 0.279, T_max = 0.548	R_int = 0.073
48014 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.31	w = 1/[σ²(F_o²) + (0.0319P)² + 27.0127P] where P = (F_o² + 2F_c²)/3
4447 reflections	Δρ_max = 1.21 e Å⁻³
291 parameters	Δρ_min = −0.92 e Å⁻³

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	0.374277 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x+1/2, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	[HgI₂(C₁₇H₁₃N₅O₂)]·C₃H₇NO
M_r	846.81
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	21.295 (4), 9.7177 (19), 24.440 (5)
V (Å³)	5057.5 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	8.56
Crystal size (mm)	0.20 × 0.18 × 0.08

Data collection
Diffractometer	Saturn724 diffractometer
Absorption correction	Numerical (CrystalClear; Rigaku/MSC, 2006)
T_min, T_max	0.279, 0.548
No. of measured, independent and observed [I > 2σ(I)] reflections	48014, 4447, 4250
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.119, 1.31
No. of reflections	4447
No. of parameters	291
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0319P)² + 27.0127P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.21, −0.92

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