Bis(μ-N,N′-di-3-pyridyl-2,6-pyridine-2,6-dicarboxamide-κ2N:N′)bis[dibrom­ido­mercury(II)] N,N-dimethyl­formamide disolvate

Huang, L.; Wu, J.

doi:10.1107/S1600536808028754

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1263

doi:10.1107/S1600536808028754

Open

access

Bis(μ-N,N′-di-3-pyridyl-2,6-pyridine-2,6-dicarboxamide-κ²N:N′)bis[dibromidomercury(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 26 August 2008; accepted 8 September 2008; online 13 September 2008)

In the dinuclear centrosymmetric title complex, [Hg₂Br₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO, the Hg^II atom is coordinated by two Br atoms and two N atoms from two different ligands in a distorted tetrahedral geometry. The solvent molecule is linked to the 28-atom ring by two hydrogen bonds.

Related literature

For related literature, see: Baer et al. (2002 ); Chae et al. (2004 and references cited therein); Qin et al. (2003 ).

Experimental

Crystal data

[Hg₂Br₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO
M_r = 1505.62
Triclinic, $[P \overline 1]$
a = 7.7609 (16) Å
b = 12.267 (3) Å
c = 13.296 (3) Å
α = 92.27 (3)°
β = 105.82 (3)°
γ = 104.07 (3)°
V = 1173.7 (4) Å³
Z = 1
Mo Kα radiation
μ = 10.00 mm⁻¹
T = 293 (2) K
0.20 × 0.18 × 0.17 mm

Data collection

Rigaku Saturn724 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ) T_min = 0.240, T_max = 0.281 (expected range = 0.156–0.183)
14249 measured reflections
5337 independent reflections
4364 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.067
S = 1.03
5337 reflections
299 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H22⋯O3ⁱ	0.859 (10)	2.08 (2)	2.891 (5)	157 (4)
N2—H21⋯O3ⁱ	0.856 (10)	2.34 (2)	3.076 (5)	144 (3)
N2—H21⋯N3	0.856 (10)	2.25 (4)	2.685 (5)	111 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028754/ng2488sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028754/ng2488Isup2.hkl

checkCIF report

Comment top

Metal-organic frameworks (MOFs) with microporous is currently of great interest because of their interesting structures and potential applications. So far, some interesting microporous MOFs have been documented (Chae et al. 2004, and references cited therein). One of the popular strategies to fabricate such compounds is to design the rigid ligands which have the ability to bridge the metal centers with big ring by utilizing their coordination sites. The rigid conjugated clamp-like multi-pyridine ligand N,N'-bis(pyridin-3-yl)-2,6-pyridinedicarboxamide has been known as a good candidate in the construction of MOFs with big ring (Qin et al. 2003; Baer et al. 2002). In this work, we selected this ligand as linker, generating a new coordination complex, [HgIIBr2(C17N5O2)](DMF), (I), which is reported here. In compound (I) each HgII atom is four-coordinated by two N atoms from two ligands and two Br atoms in a distorted tetrahedral coordination sphere (Fig. 1). The two HgII atoms are bridged with two N,N'-bis(pyridin-3-yl)-2,6-pyridinedicarboxamide ligands to form a microporous MOFs with 28-number ring. The neighbouring units are linked by the interactions to form a two-dimensional network (Fig. 2) and hydrogen bonds arising between the DMF and N,N'-bis(pyridin-3-yl)-2,6-pyridinedicarboxamide ligand (Table 2) complete the structure.

Related literature top

For related literature, see: Baer et al. (2002); Chae et al. (2004 and references cited therein); 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 HgBr2 (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 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. H atoms have been omitted.
	Fig. 2. A view of the crystal packing along the a axis. Hydrogen bonds are shown as dashed lines.
	Fig. 3. Supplementary figure.

Bis(µ-N,N'-di-3-pyridylpyridine-2,6-dicarboxamide- κ²N:N')bis[dibromidomercury(II)] N,N-dimethylformamide disolvate top

Crystal data top

[Hg₂Br₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO	Z = 1
M_r = 1505.62	F(000) = 712
Triclinic, P1	D_x = 2.130 Mg m⁻³
a = 7.7609 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.267 (3) Å	Cell parameters from 3306 reflections
c = 13.296 (3) Å	θ = 3.2–27.5°
α = 92.27 (3)°	µ = 10.00 mm⁻¹
β = 105.82 (3)°	T = 293 K
γ = 104.07 (3)°	Prism, colourless
V = 1173.7 (4) Å³	0.20 × 0.18 × 0.17 mm

Data collection top

Rigaku Saturn724 diffractometer	5337 independent reflections
Radiation source: fine-focus sealed tube	4364 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
dtprofit.ref scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −15→15
T_min = 0.240, T_max = 0.281	l = −17→17
14249 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0274P)²] where P = (F_o² + 2F_c²)/3
5337 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.61 e Å⁻³
2 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

[Hg₂Br₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO	γ = 104.07 (3)°
M_r = 1505.62	V = 1173.7 (4) Å³
Triclinic, P1	Z = 1
a = 7.7609 (16) Å	Mo Kα radiation
b = 12.267 (3) Å	µ = 10.00 mm⁻¹
c = 13.296 (3) Å	T = 293 K
α = 92.27 (3)°	0.20 × 0.18 × 0.17 mm
β = 105.82 (3)°

Data collection top

Rigaku Saturn724 diffractometer	5337 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	4364 reflections with I > 2σ(I)
T_min = 0.240, T_max = 0.281	R_int = 0.032
14249 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.61 e Å⁻³
5337 reflections	Δρ_min = −0.71 e Å⁻³
299 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	0.35413 (3)	0.143038 (15)	0.325732 (13)	0.04901 (8)
Br1	0.37301 (7)	−0.05158 (4)	0.27313 (4)	0.05602 (14)
Br2	0.63842 (7)	0.30874 (4)	0.39232 (4)	0.06222 (15)
O1	0.8838 (6)	0.5153 (3)	1.1145 (3)	0.0790 (12)
O2	0.1707 (5)	0.0697 (3)	0.7966 (2)	0.0565 (9)
N1	0.8086 (5)	0.7906 (3)	0.8251 (3)	0.0394 (8)
N2	0.7259 (5)	0.5300 (3)	0.9465 (3)	0.0399 (9)
N3	0.5289 (5)	0.3133 (3)	0.9248 (2)	0.0342 (8)
N4	0.3039 (5)	0.2237 (3)	0.7291 (3)	0.0375 (8)
N5	0.1886 (5)	0.1582 (3)	0.4441 (3)	0.0388 (8)
C1	0.9457 (6)	0.8600 (4)	0.9012 (3)	0.0410 (11)
H1	0.9948	0.9335	0.8888	0.049*
C2	1.0151 (6)	0.8257 (4)	0.9966 (3)	0.0458 (11)
H2	1.1084	0.8766	1.0485	0.055*
C3	0.9496 (6)	0.7169 (4)	1.0172 (3)	0.0429 (11)
H3	0.9979	0.6935	1.0822	0.051*
C4	0.8082 (6)	0.6423 (3)	0.9377 (3)	0.0323 (9)
C5	0.7417 (6)	0.6847 (3)	0.8436 (3)	0.0356 (10)
H5	0.6454	0.6369	0.7907	0.043*
C6	0.7650 (6)	0.4739 (4)	1.0323 (3)	0.0423 (11)
C7	0.6516 (6)	0.3533 (3)	1.0186 (3)	0.0376 (10)
C8	0.6773 (7)	0.2900 (4)	1.1030 (3)	0.0466 (12)
H8	0.7648	0.3211	1.1670	0.056*
C9	0.5708 (7)	0.1802 (4)	1.0900 (3)	0.0477 (12)
H9	0.5851	0.1356	1.1451	0.057*
C10	0.4421 (6)	0.1373 (4)	0.9935 (4)	0.0421 (11)
H10	0.3679	0.0633	0.9827	0.050*
C11	0.4256 (6)	0.2061 (3)	0.9135 (3)	0.0353 (10)
C12	0.2874 (6)	0.1602 (3)	0.8079 (3)	0.0380 (10)
C13	0.1959 (6)	0.1874 (3)	0.6234 (3)	0.0352 (10)
C14	0.0045 (6)	0.1485 (3)	0.5954 (4)	0.0418 (11)
H14	−0.0582	0.1444	0.6462	0.050*
C15	−0.0910 (6)	0.1160 (4)	0.4913 (4)	0.0468 (12)
H15	−0.2198	0.0901	0.4707	0.056*
C16	0.0035 (7)	0.1218 (4)	0.4176 (4)	0.0463 (11)
H16	−0.0629	0.0998	0.3472	0.056*
C17	0.2825 (6)	0.1910 (3)	0.5445 (3)	0.0343 (9)
H17	0.4111	0.2175	0.5627	0.041*
H22	0.396 (4)	0.283 (2)	0.745 (3)	0.044 (13)*
H21	0.642 (4)	0.491 (3)	0.8924 (19)	0.039 (12)*
O3	0.4162 (5)	0.5774 (3)	0.2838 (2)	0.0568 (9)
N6	0.1662 (6)	0.5374 (3)	0.3463 (3)	0.0465 (10)
C18	−0.0003 (7)	0.5662 (5)	0.3550 (4)	0.0653 (15)
H18A	−0.0186	0.6282	0.3152	0.098*
H18B	0.0132	0.5875	0.4275	0.098*
H18C	−0.1054	0.5019	0.3280	0.098*
C19	0.2125 (9)	0.4419 (4)	0.3969 (4)	0.0719 (17)
H19A	0.3199	0.4287	0.3813	0.108*
H19B	0.1099	0.3759	0.3715	0.108*
H19C	0.2385	0.4576	0.4716	0.108*
C20	0.2735 (8)	0.5963 (4)	0.2962 (3)	0.0503 (12)
H20A	0.2392	0.6583	0.2671	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.06762 (15)	0.04080 (12)	0.03641 (11)	0.01450 (9)	0.01118 (9)	0.00594 (8)
Br1	0.0631 (3)	0.0433 (3)	0.0679 (3)	0.0189 (2)	0.0251 (3)	0.0047 (2)
Br2	0.0546 (3)	0.0547 (3)	0.0623 (3)	0.0063 (3)	0.0000 (3)	0.0042 (3)
O1	0.105 (3)	0.053 (2)	0.039 (2)	−0.011 (2)	−0.016 (2)	0.0158 (17)
O2	0.067 (2)	0.0389 (18)	0.049 (2)	−0.0133 (17)	0.0173 (17)	0.0083 (16)
N1	0.044 (2)	0.035 (2)	0.0344 (19)	0.0063 (17)	0.0071 (17)	0.0039 (16)
N2	0.047 (2)	0.037 (2)	0.0269 (19)	0.0029 (18)	0.0026 (17)	0.0033 (17)
N3	0.041 (2)	0.0331 (19)	0.0315 (19)	0.0101 (16)	0.0143 (16)	0.0078 (16)
N4	0.042 (2)	0.0298 (19)	0.034 (2)	−0.0031 (17)	0.0113 (17)	0.0018 (16)
N5	0.048 (2)	0.0330 (19)	0.0318 (19)	0.0080 (17)	0.0082 (17)	0.0027 (16)
C1	0.044 (3)	0.031 (2)	0.045 (3)	0.004 (2)	0.013 (2)	0.005 (2)
C2	0.045 (3)	0.043 (3)	0.036 (2)	−0.002 (2)	0.001 (2)	0.001 (2)
C3	0.044 (3)	0.040 (3)	0.035 (2)	0.006 (2)	0.001 (2)	0.004 (2)
C4	0.036 (2)	0.031 (2)	0.028 (2)	0.0082 (18)	0.0086 (18)	0.0045 (17)
C5	0.040 (3)	0.033 (2)	0.027 (2)	0.0048 (19)	0.0043 (19)	0.0013 (18)
C6	0.052 (3)	0.040 (3)	0.030 (2)	0.010 (2)	0.005 (2)	0.010 (2)
C7	0.046 (3)	0.038 (2)	0.033 (2)	0.013 (2)	0.014 (2)	0.011 (2)
C8	0.056 (3)	0.051 (3)	0.036 (2)	0.014 (2)	0.016 (2)	0.012 (2)
C9	0.060 (3)	0.048 (3)	0.038 (3)	0.014 (2)	0.018 (2)	0.018 (2)
C10	0.052 (3)	0.034 (2)	0.050 (3)	0.013 (2)	0.027 (2)	0.012 (2)
C11	0.044 (3)	0.030 (2)	0.036 (2)	0.0066 (19)	0.021 (2)	0.0063 (18)
C12	0.044 (3)	0.032 (2)	0.042 (3)	0.009 (2)	0.020 (2)	0.004 (2)
C13	0.039 (3)	0.027 (2)	0.038 (2)	0.0062 (18)	0.011 (2)	0.0052 (18)
C14	0.041 (3)	0.033 (2)	0.054 (3)	0.010 (2)	0.018 (2)	0.006 (2)
C15	0.040 (3)	0.032 (2)	0.060 (3)	0.007 (2)	0.003 (2)	0.004 (2)
C16	0.057 (3)	0.033 (2)	0.042 (3)	0.014 (2)	0.000 (2)	0.004 (2)
C17	0.036 (2)	0.032 (2)	0.032 (2)	0.0054 (18)	0.0080 (19)	0.0023 (18)
O3	0.059 (2)	0.053 (2)	0.052 (2)	−0.0049 (18)	0.0235 (18)	0.0038 (17)
N6	0.058 (3)	0.038 (2)	0.044 (2)	0.0050 (19)	0.021 (2)	0.0033 (18)
C18	0.063 (4)	0.070 (4)	0.063 (4)	0.018 (3)	0.022 (3)	−0.010 (3)
C19	0.104 (5)	0.049 (3)	0.080 (4)	0.024 (3)	0.048 (4)	0.023 (3)
C20	0.065 (3)	0.041 (3)	0.036 (3)	0.002 (3)	0.010 (3)	0.000 (2)

Geometric parameters (Å, º) top

Hg1—N5	2.315 (3)	C7—C8	1.386 (6)
Hg1—N1ⁱ	2.351 (3)	C8—C9	1.374 (6)
Hg1—Br1	2.5108 (8)	C8—H8	0.9300
Hg1—Br2	2.5289 (12)	C9—C10	1.383 (6)
O1—C6	1.218 (5)	C9—H9	0.9300
O2—C12	1.225 (5)	C10—C11	1.382 (6)
N1—C5	1.335 (5)	C10—H10	0.9300
N1—C1	1.337 (5)	C11—C12	1.503 (6)
N1—Hg1ⁱ	2.351 (3)	C13—C14	1.384 (6)
N2—C6	1.357 (5)	C13—C17	1.389 (5)
N2—C4	1.394 (5)	C14—C15	1.369 (6)
N2—H21	0.856 (10)	C14—H14	0.9300
N3—C7	1.334 (5)	C15—C16	1.370 (6)
N3—C11	1.342 (5)	C15—H15	0.9300
N4—C12	1.346 (5)	C16—H16	0.9300
N4—C13	1.414 (5)	C17—H17	0.9300
N4—H22	0.859 (10)	O3—C20	1.236 (6)
N5—C17	1.326 (5)	N6—C20	1.306 (6)
N5—C16	1.337 (6)	N6—C19	1.446 (6)
C1—C2	1.361 (6)	N6—C18	1.452 (6)
C1—H1	0.9300	C18—H18A	0.9600
C2—C3	1.374 (6)	C18—H18B	0.9600
C2—H2	0.9300	C18—H18C	0.9600
C3—C4	1.401 (5)	C19—H19A	0.9600
C3—H3	0.9300	C19—H19B	0.9600
C4—C5	1.390 (5)	C19—H19C	0.9600
C5—H5	0.9300	C20—H20A	0.9300
C6—C7	1.502 (6)

N5—Hg1—N1ⁱ	103.47 (12)	C8—C9—H9	120.6
N5—Hg1—Br1	117.00 (9)	C10—C9—H9	120.6
N1ⁱ—Hg1—Br1	107.93 (9)	C11—C10—C9	118.8 (4)
N5—Hg1—Br2	102.81 (9)	C11—C10—H10	120.6
N1ⁱ—Hg1—Br2	100.41 (9)	C9—C10—H10	120.6
Br1—Hg1—Br2	122.54 (3)	N3—C11—C10	123.1 (4)
C5—N1—C1	118.4 (4)	N3—C11—C12	117.5 (3)
C5—N1—Hg1ⁱ	118.6 (3)	C10—C11—C12	119.4 (4)
C1—N1—Hg1ⁱ	122.0 (3)	O2—C12—N4	123.6 (4)
C6—N2—C4	126.9 (4)	O2—C12—C11	120.7 (4)
C6—N2—H21	116 (3)	N4—C12—C11	115.7 (4)
C4—N2—H21	118 (3)	C14—C13—C17	118.3 (4)
C7—N3—C11	117.1 (3)	C14—C13—N4	122.0 (4)
C12—N4—C13	122.6 (4)	C17—C13—N4	119.8 (4)
C12—N4—H22	116 (3)	C15—C14—C13	118.7 (4)
C13—N4—H22	121 (3)	C15—C14—H14	120.7
C17—N5—C16	118.9 (4)	C13—C14—H14	120.7
C17—N5—Hg1	118.2 (3)	C14—C15—C16	119.9 (4)
C16—N5—Hg1	122.4 (3)	C14—C15—H15	120.0
N1—C1—C2	121.6 (4)	C16—C15—H15	120.0
N1—C1—H1	119.2	N5—C16—C15	121.8 (4)
C2—C1—H1	119.2	N5—C16—H16	119.1
C1—C2—C3	121.0 (4)	C15—C16—H16	119.1
C1—C2—H2	119.5	N5—C17—C13	122.5 (4)
C3—C2—H2	119.5	N5—C17—H17	118.8
C2—C3—C4	118.2 (4)	C13—C17—H17	118.8
C2—C3—H3	120.9	C20—N6—C19	120.5 (4)
C4—C3—H3	120.9	C20—N6—C18	121.7 (4)
C5—C4—N2	117.6 (4)	C19—N6—C18	117.7 (4)
C5—C4—C3	117.2 (4)	N6—C18—H18A	109.5
N2—C4—C3	125.2 (4)	N6—C18—H18B	109.5
N1—C5—C4	123.5 (4)	H18A—C18—H18B	109.5
N1—C5—H5	118.2	N6—C18—H18C	109.5
C4—C5—H5	118.2	H18A—C18—H18C	109.5
O1—C6—N2	124.0 (4)	H18B—C18—H18C	109.5
O1—C6—C7	121.1 (4)	N6—C19—H19A	109.5
N2—C6—C7	114.9 (4)	N6—C19—H19B	109.5
N3—C7—C8	123.5 (4)	H19A—C19—H19B	109.5
N3—C7—C6	117.3 (3)	N6—C19—H19C	109.5
C8—C7—C6	119.2 (4)	H19A—C19—H19C	109.5
C9—C8—C7	118.7 (4)	H19B—C19—H19C	109.5
C9—C8—H8	120.7	O3—C20—N6	126.2 (5)
C7—C8—H8	120.7	O3—C20—H20A	116.9
C8—C9—C10	118.8 (4)	N6—C20—H20A	116.9

N1ⁱ—Hg1—N5—C17	−141.8 (3)	C6—C7—C8—C9	179.1 (4)
Br1—Hg1—N5—C17	99.7 (3)	C7—C8—C9—C10	−0.1 (7)
Br2—Hg1—N5—C17	−37.6 (3)	C8—C9—C10—C11	0.2 (7)
N1ⁱ—Hg1—N5—C16	46.8 (3)	C7—N3—C11—C10	−0.3 (6)
Br1—Hg1—N5—C16	−71.7 (3)	C7—N3—C11—C12	−179.8 (3)
Br2—Hg1—N5—C16	151.0 (3)	C9—C10—C11—N3	0.0 (6)
C5—N1—C1—C2	−1.1 (6)	C9—C10—C11—C12	179.5 (4)
Hg1ⁱ—N1—C1—C2	167.2 (3)	C13—N4—C12—O2	−4.8 (7)
N1—C1—C2—C3	1.6 (7)	C13—N4—C12—C11	174.0 (4)
C1—C2—C3—C4	−0.5 (7)	N3—C11—C12—O2	−169.3 (4)
C6—N2—C4—C5	−177.3 (4)	C10—C11—C12—O2	11.2 (6)
C6—N2—C4—C3	0.9 (7)	N3—C11—C12—N4	11.9 (6)
C2—C3—C4—C5	−1.1 (6)	C10—C11—C12—N4	−167.7 (4)
C2—C3—C4—N2	−179.4 (4)	C12—N4—C13—C14	51.7 (6)
C1—N1—C5—C4	−0.7 (6)	C12—N4—C13—C17	−128.8 (4)
Hg1ⁱ—N1—C5—C4	−169.4 (3)	C17—C13—C14—C15	−0.4 (6)
N2—C4—C5—N1	−179.9 (4)	N4—C13—C14—C15	179.2 (4)
C3—C4—C5—N1	1.8 (6)	C13—C14—C15—C16	0.5 (6)
C4—N2—C6—O1	−1.7 (8)	C17—N5—C16—C15	−1.0 (6)
C4—N2—C6—C7	179.3 (4)	Hg1—N5—C16—C15	170.4 (3)
C11—N3—C7—C8	0.4 (6)	C14—C15—C16—N5	0.2 (7)
C11—N3—C7—C6	−178.9 (4)	C16—N5—C17—C13	1.0 (6)
O1—C6—C7—N3	−177.7 (4)	Hg1—N5—C17—C13	−170.7 (3)
N2—C6—C7—N3	1.3 (6)	C14—C13—C17—N5	−0.3 (6)
O1—C6—C7—C8	3.0 (7)	N4—C13—C17—N5	−179.9 (4)
N2—C6—C7—C8	−178.0 (4)	C19—N6—C20—O3	2.1 (7)
N3—C7—C8—C9	−0.2 (7)	C18—N6—C20—O3	−179.2 (5)

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
N4—H22···O3ⁱ	0.86 (1)	2.08 (2)	2.891 (5)	157 (4)
N2—H21···O3ⁱ	0.86 (1)	2.34 (2)	3.076 (5)	144 (3)
N2—H21···N3	0.86 (1)	2.25 (4)	2.685 (5)	111 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Hg₂Br₄(C₁₇H₁₃N₅O₂)₂]·2C₃H₇NO
M_r	1505.62
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.7609 (16), 12.267 (3), 13.296 (3)
α, β, γ (°)	92.27 (3), 105.82 (3), 104.07 (3)
V (Å³)	1173.7 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	10.00
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Rigaku Saturn724 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2006)
T_min, T_max	0.240, 0.281
No. of measured, independent and observed [I > 2σ(I)] reflections	14249, 5337, 4364
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.067, 1.03
No. of reflections	5337
No. of parameters	299
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.71

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H22···O3ⁱ	0.859 (10)	2.08 (2)	2.891 (5)	157 (4)
N2—H21···O3ⁱ	0.856 (10)	2.34 (2)	3.076 (5)	144 (3)
N2—H21···N3	0.856 (10)	2.25 (4)	2.685 (5)	111 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

Baer, A. J., Koivisto, B. D., Coté, A. P., 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
Chae, H. E., Siberio-Pérez, D. Y., Kim, J., Go, Y., Eddaoudi, M., Matzger, A. J., O'Keeffe, M. & Yaghi, O. M. (2004). Nature (London), 427, 523–527. Web of Science CSD 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1263

doi:10.1107/S1600536808028754

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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