Crystal structure of an HgII coordination polymer with an unsymmetrical dipyridyl ligand: catena-poly[[[di­chlorido­mercury(II)]-μ-N-(pyridin-4-ylmeth­yl)pyridin-3-amine-κ2N:N′] chloro­form hemisolvate]

Moon, S.-H.; Kang, D.; Park, K.-M.

doi:10.1107/S2056989016015310

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 72| Part 11| November 2016| Pages 1513-1516

https://doi.org/10.1107/S2056989016015310

Open

access

Crystal structure of an Hg^II coordination polymer with an unsymmetrical dipyridyl ligand: catena-poly[[[dichloridomercury(II)]-μ-N-(pyridin-4-ylmethyl)pyridin-3-amine-κ²N:N′] chloroform hemisolvate]

Suk-Hee Moon,^a Donghyun Kang ^b ^* and Ki-Min Park ^c ^*

^aDepartment of Food and Nutrition, Kyungnam College of Information and Technology, Busan 47011, Republic of Korea, ^bDepartment of Science Education, Kyungnam University, Changwon 51767, Republic of Korea, and ^cResearch Institute of Natural Science, Gyeongsang National University, Jinju 52828, Republic of Korea
^*Correspondence e-mail: dh2232@kyungnam.ac.kr, kmpark@gnu.ac.kr

Edited by J. Simpson, University of Otago, New Zealand (Received 28 September 2016; accepted 29 September 2016; online 4 October 2016)

The asymmetric unit of the title compound, {[HgLCl₂]·0.5CHCl₃}_n (L = N-(pyridin-4-ylmethyl)pyridin-3-amine, C₁₁H₁₁N₃), contains one Hg^II ion, one bridging L ligand, two chloride ligands and a chloroform solvent molecule with half-occupancy that is disordered about a crystallographic twofold rotation axis. Each Hg^II ion is coordinated by two pyridine N atoms from two symmetry-related L ligands and two chloride anions in a highly distorted tetrahedral geometry with bond angles falling in the range 99.05 (17)–142.96 (7)°. Each L ligand bridges two Hg^II ions, forming polymeric zigzag chains propagating in [010]. In the crystal, the chains are linked by intermolecular N/C—H⋯Cl hydrogen bonds together with weak C—H⋯π interactions, resulting in the formation of a three-dimensional supramolecular network, which is further stabilized by C—Cl⋯π interactions between the solvent chloroform molecules and the pyridine rings of L [chloride-to-centroid distances = 3.442 (11) and 3.626 (13) Å]. In addition, weak Cl⋯Cl contacts [3.320 (5) Å] between the chloroform solvent molecules and the coordinating chloride anions are also observed.

Keywords: crystal structure; Hg^II compound; unsymmetrical dipyridyl ligand; zigzag coordination polymer.

CCDC reference: 1507232

1. Chemical context

A variety of coordination polymers have been explored extensively over the last two decades because of their fascinating architectures and their useful applications in materials chemistry (Silva et al., 2015 ; Furukawa et al., 2014 ; Robson, 2008 ; Leong & Vittal, 2011 ). In this area of research, symmetrical dipyridyl ligands composed of two terminal pyridines with same substituted nitrogen positions have been used mainly for the design and construction of the coordination polymers. By contrast, investigations based on unsymmetrical dipyridyl ligands, with the nitrogen atoms in different positions on each of the two terminal pyridines, are still rare (Uemura et al., 2008 ; Khlobystov et al., 2003 ). Recently, our group and that of Gao have already reported Ag^I coordination polymers with some unsymmetrical dipyridyl ligands such as N-(pyridine-3-ylmethyl)pyridine-2-amine (Lee et al., 2013 ; Zhang et al., 2013 ), N-(pyridine-2-ylmethyl)pyridine-3-amine (Ju et al., 2014 ; Moon & Park, 2014 ; Moon et al., 2014 ; Zhang et al., 2013) and N-(pyridine-4-ylmethyl)pyridine-3-amine (Lee et al., 2015 ; Moon et al., 2015 ; Zhang et al., 2013). As a part of our ongoing efforts to construct coordination polymers with such unsymmetrical dipyridyl ligands, we prepared the title compound obtained by the reaction of mercury(II) chloride with an unsymmetrical dipyridyl ligand, namely N-(pyridine-4-ylmethyl)pyridine-3-amine, synthesized according to a literature procedure (Lee et al., 2013). Herein, we report the crystal structure of the title compound.

2. Structural commentary

The asymmetric unit of the title compound, {[HgLCl₂]·0.5CHCl₃}_n, L = N-(pyridine-4-ylmethyl)pyridine-3-amine, C₁₁H₁₁N₃, comprises one Hg^II ion, one L ligand, two chloride anions and one half-molecule of chloroform. The solvent molecule is disordered over two orientations of equal occupancy about the crystallographic twofold rotation axis. As shown in Fig. 1, the coordination geometry of each Hg^II ion is highly distorted tetrahedral with two coordination sites being occupied by two pyridine N atoms from two symmetry-related L ligands. The geometry of the Hg^II ion is completed by the coordination of two chloride ions. The tetrahedral angles around the Hg^II ion fall in the range of 99.05 (17)–142.96 (7)° (Table 1).

Table 1
Selected geometric parameters (Å, °)

Hg1—N1	2.367 (5)	Hg1—Cl1	2.3759 (18)
Hg1—Cl2	2.3718 (19)	Hg1—N2ⁱ	2.385 (5)

N1—Hg1—Cl2	103.82 (14)	N1—Hg1—N2ⁱ	99.05 (17)
N1—Hg1—Cl1	102.31 (14)	Cl2—Hg1—N2ⁱ	101.20 (14)
Cl2—Hg1—Cl1	142.96 (7)	Cl1—Hg1—N2ⁱ	100.11 (13)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
A view of the molecular structure of the title compound, showing the atom-numbering scheme [symmetry code: (i) −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ]. Displacement ellipsoids are drawn at the 30% probability level. Only one component of the disordered chloroform molecule is shown. The dashed line represents the intermolecular C—Cl⋯π interaction [Cl4⋯Cg2 = 3.442 (11) Å; Cg2 is the centroid of the N2/C7–C11 ring].

Each L ligand bridges two Hg^II ions into an infinite zigzag chain propagating along the b axis (Fig. 2). The separation between the Hg^II ions through a L ligand in the chain is 8.1033 (6) Å. In the L ligand, the C_py—N—C—C_py torsion angle is −70.9 (7)° while the dihedral angle between two terminal pyridine ring planes is 85.0 (2)°. The conformation of the L ligand, along with the the N_py—Hg—N_py coordination angle [99.05 (17)°], may induce the zigzag topology of the chain.

Figure 2
The layer formed through intermolecular N—H⋯Cl hydrogen bonds (black dashed lines) and weak C—H⋯π interactions (red dashed lines). Disordered chloroform molecules and intermolecular C—Cl⋯π interactions are shown as two-colored dashed lines and yellow dashed lines, respectively. H atoms not involved in intermolecular interactions have been omitted for clarity.

3. Supramolecular features

In the crystal, adjacent zigzag chains are linked by intermolecular N—H⋯Cl hydrogen bonds and weak intermolecular C—H⋯π interactions (Table 2), forming a layer extending parallel to the bc plane (Figs. 2 and 3). Furthermore, neighboring layers are packed by C—H⋯Cl hydrogen bonds (Table 2), resulting in the formation of a three-dimensional supramolecular network (Fig. 3). This three-dimensional network is further stabilized by C—Cl⋯π interactions (Chifotides & Dunbar, 2013 ; Matter et al., 2009 ) between the solvent chloroform molecules and the pyridine rings of L with Cl4⋯Cg2 = 3.442 (11) Å, C12—Cl4⋯Cg2 = 170.7 (8)°, Cl5⋯Cg2^iv = 3.626 (13) Å and C12—Cl5⋯Cg2^iv 144.1 (8)° [yellow dashed lines in Figs. 1, 2 and 3; Cg2 is the centroid of the N2/C7–C11 ring; symmetry code: (iv) −x, y, −z + $[{1\over 2}]$ ]. In addition, weak intermolecular Cl⋯Cl contacts between the solvent chloroform molecule and the coordinating chloride anion [Cl1⋯Cl3^v = 3.320 (5) Å, Hg1—Cl1⋯Cl3^v = 126.70 (14) and Cl1⋯Cl3^v—C12^v = 169.2 (8)°; symmetry code: (v) x + $[{1\over 2}]$ , y + $[{3\over 2}]$ , z] are observed.

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1–C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Cl2ⁱⁱ	0.86	2.78	3.467 (5)	138
C8—H8⋯Cl1ⁱⁱⁱ	0.93	2.80	3.654 (6)	153
C6—H6B⋯Cg1ⁱⁱ	0.97	2.71	3.465 (7)	135
Symmetry codes: (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Figure 3
The three-dimensional supramolecular network constructed through intermolecular C—H⋯Cl hydrogen bonds (light-blue dashed lines) and C—Cl⋯π interactions (yellow dashed lines) between the layers formed through N—H⋯Cl (black dashed lines) and C—H⋯π (red dashed lines) interactions. Disordered chloroform molecules are shown as two-colored dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity.

4. Synthesis and crystallization

The L ligand was synthesized according to a literature method (Lee et al., 2013). X-ray-quality single crystals of the title compound were obtained by slow diffusion of a methanol solution of HgCl₂ into a chloroform solution of the L ligand.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. A reflection affected by the beamstop was omitted from the final refinement. The chloroform molecule is disordered over two sets of sites about a twofold rotation axis with equal occupancy. The C—Cl bond lengths were restrained using the DFIX instructions in SHELXL2014/7 (Sheldrick, 2015 ). All H atoms were positioned geometrically with d(C—H) = 0.93 Å for Csp²—H, 0.97 Å for methylene C—H, 0.98 Å for methine C—H, and 0.86 Å for amine N—H, and were refined as riding with U_iso(H) = 1.2U_eq(C,N).

Table 3
Experimental details

Crystal data
Chemical formula	[HgCl₂(C₁₁H₁₁N₃)]·0.5CHCl₃
M_r	516.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	16.6906 (14), 9.1942 (8), 21.0159 (17)
β (°)	95.501 (2)
V (Å³)	3210.2 (5)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	10.16
Crystal size (mm)	0.4 × 0.3 × 0.3

Data collection
Diffractometer	Bruker APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.521, 0.928
No. of measured, independent and observed [I > 2σ(I)] reflections	8852, 3151, 2189
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.074, 0.99
No. of reflections	3151
No. of parameters	190
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.83
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015) and DIAMOND (Brandenburg, 2010 ).

Supporting information

CCDC reference: 1507232

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989016015310/sj5509sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016015310/sj5509Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

catena-Poly[[[dichloridomercury(II)]-µ-N- (pyridin-4-ylmethyl)pyridin-3-amine-κ²N:N'] chloroform hemisolvate] top

Crystal data top

[HgCl₂(C₁₁H₁₁N₃)]·0.5CHCl₃	F(000) = 1928
M_r = 516.40	D_x = 2.137 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.6906 (14) Å	Cell parameters from 3870 reflections
b = 9.1942 (8) Å	θ = 2.0–28.3°
c = 21.0159 (17) Å	µ = 10.16 mm⁻¹
β = 95.501 (2)°	T = 298 K
V = 3210.2 (5) Å³	Block, colorless
Z = 8	0.4 × 0.3 × 0.3 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	2189 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.044
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 26.0°, θ_min = 2.5°
T_min = 0.521, T_max = 0.928	h = −12→20
8852 measured reflections	k = −11→10
3151 independent reflections	l = −24→25

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.034P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
3151 reflections	Δρ_max = 0.58 e Å⁻³
190 parameters	Δρ_min = −0.83 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Hg1	0.32126 (2)	0.66479 (3)	0.10699 (2)	0.06180 (11)
Cl1	0.44104 (11)	0.8055 (2)	0.11123 (9)	0.0766 (5)
Cl2	0.18389 (11)	0.6629 (2)	0.06581 (9)	0.0839 (6)
N1	0.3676 (3)	0.4300 (6)	0.0825 (2)	0.0548 (13)
N2	0.1898 (3)	0.1323 (5)	0.2816 (2)	0.0568 (13)
N3	0.2853 (4)	0.0648 (6)	0.0611 (2)	0.0641 (15)
H3	0.3015	−0.0182	0.0486	0.077*
C1	0.3176 (4)	0.3179 (7)	0.0811 (3)	0.0522 (15)
H1	0.2663	0.3330	0.0938	0.063*
C2	0.4398 (4)	0.4134 (8)	0.0648 (3)	0.0693 (18)
H2	0.4749	0.4922	0.0662	0.083*
C3	0.4649 (5)	0.2790 (10)	0.0439 (4)	0.080 (2)
H3A	0.5163	0.2687	0.0310	0.096*
C4	0.4152 (5)	0.1641 (8)	0.0423 (3)	0.075 (2)
H4	0.4322	0.0742	0.0284	0.090*
C5	0.3372 (4)	0.1798 (7)	0.0618 (3)	0.0562 (16)
C6	0.2052 (4)	0.0749 (7)	0.0800 (3)	0.0615 (17)
H6A	0.1761	−0.0130	0.0667	0.074*
H6B	0.1780	0.1559	0.0576	0.074*
C7	0.2007 (4)	0.0955 (7)	0.1513 (2)	0.0499 (15)
C8	0.1386 (4)	0.1686 (7)	0.1738 (3)	0.0636 (17)
H8	0.0986	0.2093	0.1454	0.076*
C9	0.1348 (4)	0.1821 (7)	0.2375 (3)	0.0664 (18)
H9	0.0904	0.2298	0.2512	0.080*
C10	0.2502 (4)	0.0629 (7)	0.2600 (3)	0.0677 (19)
H10	0.2895	0.0249	0.2897	0.081*
C11	0.2594 (4)	0.0424 (7)	0.1953 (3)	0.0618 (18)
H11	0.3040	−0.0060	0.1825	0.074*
C12	0.0095 (13)	−0.2965 (16)	0.2726 (7)	0.128 (8)	0.5
H12	0.0355	−0.3356	0.3128	0.153*	0.5
Cl3	−0.0016 (4)	−0.4392 (6)	0.2177 (3)	0.1288 (19)	0.5
Cl4	0.0705 (7)	−0.1706 (11)	0.2464 (6)	0.201 (5)	0.5
Cl5	−0.0803 (8)	−0.2208 (14)	0.2885 (6)	0.230 (7)	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.06149 (17)	0.07271 (18)	0.05193 (16)	0.00720 (15)	0.00918 (12)	−0.00275 (14)
Cl1	0.0576 (10)	0.0833 (12)	0.0887 (13)	0.0035 (9)	0.0056 (10)	0.0198 (10)
Cl2	0.0639 (11)	0.1104 (15)	0.0748 (11)	0.0191 (11)	−0.0065 (9)	−0.0262 (11)
N1	0.052 (3)	0.069 (3)	0.044 (3)	0.012 (3)	0.006 (3)	−0.001 (2)
N2	0.053 (3)	0.078 (4)	0.040 (3)	0.007 (3)	0.009 (3)	0.006 (2)
N3	0.096 (4)	0.052 (3)	0.047 (3)	0.018 (3)	0.019 (3)	−0.004 (2)
C1	0.053 (4)	0.063 (4)	0.041 (3)	0.017 (3)	0.007 (3)	−0.001 (3)
C2	0.056 (4)	0.083 (5)	0.070 (4)	0.019 (4)	0.011 (4)	0.008 (4)
C3	0.065 (5)	0.097 (6)	0.083 (6)	0.030 (5)	0.026 (4)	0.020 (5)
C4	0.099 (6)	0.072 (5)	0.057 (4)	0.032 (5)	0.027 (4)	0.010 (4)
C5	0.070 (4)	0.066 (4)	0.034 (3)	0.023 (4)	0.010 (3)	0.007 (3)
C6	0.074 (5)	0.061 (4)	0.047 (4)	0.002 (4)	−0.004 (4)	0.001 (3)
C7	0.061 (4)	0.053 (3)	0.036 (3)	0.000 (3)	0.002 (3)	0.006 (3)
C8	0.052 (4)	0.082 (4)	0.053 (4)	0.017 (4)	−0.011 (3)	0.007 (4)
C9	0.052 (4)	0.089 (5)	0.059 (4)	0.015 (4)	0.005 (3)	−0.002 (4)
C10	0.065 (4)	0.083 (5)	0.055 (4)	0.018 (4)	0.004 (4)	0.017 (3)
C11	0.061 (4)	0.083 (5)	0.042 (3)	0.029 (4)	0.008 (3)	0.003 (3)
C12	0.18 (2)	0.108 (14)	0.098 (18)	0.000 (18)	0.04 (2)	−0.024 (10)
Cl3	0.147 (5)	0.100 (3)	0.135 (4)	−0.006 (4)	−0.011 (5)	−0.026 (3)
Cl4	0.208 (10)	0.167 (7)	0.234 (11)	−0.120 (7)	0.051 (8)	−0.057 (7)
Cl5	0.184 (9)	0.242 (12)	0.281 (15)	−0.077 (9)	0.110 (10)	−0.150 (11)

Geometric parameters (Å, º) top

Hg1—N1	2.367 (5)	C4—C5	1.409 (10)
Hg1—Cl2	2.3718 (19)	C4—H4	0.9300
Hg1—Cl1	2.3759 (18)	C6—C7	1.519 (7)
Hg1—N2ⁱ	2.385 (5)	C6—H6A	0.9700
N1—C2	1.303 (8)	C6—H6B	0.9700
N1—C1	1.326 (8)	C7—C8	1.358 (8)
N2—C10	1.310 (8)	C7—C11	1.371 (8)
N2—C9	1.323 (8)	C8—C9	1.352 (9)
N2—Hg1ⁱⁱ	2.386 (5)	C8—H8	0.9300
N3—C5	1.366 (8)	C9—H9	0.9300
N3—C6	1.434 (8)	C10—C11	1.394 (8)
N3—H3	0.8600	C10—H10	0.9300
C1—C5	1.382 (8)	C11—H11	0.9300
C1—H1	0.9300	C12—Cl4	1.670 (15)
C2—C3	1.389 (11)	C12—Cl5	1.713 (17)
C2—H2	0.9300	C12—Cl3	1.746 (13)
C3—C4	1.342 (10)	C12—H12	0.9800
C3—H3A	0.9300

N1—Hg1—Cl2	103.82 (14)	C1—C5—C4	115.5 (7)
N1—Hg1—Cl1	102.31 (14)	N3—C6—C7	114.6 (5)
Cl2—Hg1—Cl1	142.96 (7)	N3—C6—H6A	108.6
N1—Hg1—N2ⁱ	99.05 (17)	C7—C6—H6A	108.6
Cl2—Hg1—N2ⁱ	101.20 (14)	N3—C6—H6B	108.6
Cl1—Hg1—N2ⁱ	100.11 (13)	C7—C6—H6B	108.6
C2—N1—C1	120.0 (6)	H6A—C6—H6B	107.6
C2—N1—Hg1	120.0 (5)	C8—C7—C11	117.5 (5)
C1—N1—Hg1	119.7 (4)	C8—C7—C6	121.0 (5)
C10—N2—C9	115.6 (5)	C11—C7—C6	121.5 (6)
C10—N2—Hg1ⁱⁱ	122.4 (4)	C9—C8—C7	119.9 (6)
C9—N2—Hg1ⁱⁱ	122.0 (4)	C9—C8—H8	120.0
C5—N3—C6	123.7 (5)	C7—C8—H8	120.0
C5—N3—H3	118.2	N2—C9—C8	124.5 (6)
C6—N3—H3	118.2	N2—C9—H9	117.7
N1—C1—C5	123.7 (6)	C8—C9—H9	117.7
N1—C1—H1	118.2	N2—C10—C11	124.3 (6)
C5—C1—H1	118.2	N2—C10—H10	117.8
N1—C2—C3	120.6 (7)	C11—C10—H10	117.8
N1—C2—H2	119.7	C7—C11—C10	118.1 (6)
C3—C2—H2	119.7	C7—C11—H11	120.9
C4—C3—C2	120.3 (7)	C10—C11—H11	120.9
C4—C3—H3A	119.8	Cl4—C12—Cl5	110.8 (10)
C2—C3—H3A	119.8	Cl4—C12—Cl3	109.4 (9)
C3—C4—C5	119.9 (7)	Cl5—C12—Cl3	113.3 (11)
C3—C4—H4	120.1	Cl4—C12—H12	107.7
C5—C4—H4	120.1	Cl5—C12—H12	107.7
N3—C5—C1	123.1 (6)	Cl3—C12—H12	107.7
N3—C5—C4	121.4 (6)

C2—N1—C1—C5	0.3 (9)	N3—C6—C7—C8	150.4 (6)
Hg1—N1—C1—C5	174.1 (4)	N3—C6—C7—C11	−29.1 (9)
C1—N1—C2—C3	0.6 (9)	C11—C7—C8—C9	−2.3 (10)
Hg1—N1—C2—C3	−173.3 (5)	C6—C7—C8—C9	178.2 (6)
N1—C2—C3—C4	−0.8 (11)	C10—N2—C9—C8	−1.6 (10)
C2—C3—C4—C5	0.1 (11)	Hg1ⁱⁱ—N2—C9—C8	179.0 (5)
C6—N3—C5—C1	0.1 (9)	C7—C8—C9—N2	2.3 (11)
C6—N3—C5—C4	−179.6 (5)	C9—N2—C10—C11	1.1 (10)
N1—C1—C5—N3	179.5 (5)	Hg1ⁱⁱ—N2—C10—C11	−179.5 (5)
N1—C1—C5—C4	−0.8 (9)	C8—C7—C11—C10	1.9 (10)
C3—C4—C5—N3	−179.7 (6)	C6—C7—C11—C10	−178.7 (6)
C3—C4—C5—C1	0.6 (9)	N2—C10—C11—C7	−1.4 (11)
C5—N3—C6—C7	−70.9 (7)

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1–C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cl2ⁱⁱⁱ	0.86	2.78	3.467 (5)	138
C8—H8···Cl1^iv	0.93	2.80	3.654 (6)	153
C6—H6B···Cg1ⁱⁱⁱ	0.97	2.71	3.465 (7)	135

Symmetry codes: (iii) −x+1/2, −y+1/2, −z; (iv) x−1/2, y−1/2, z.

Acknowledgements

This work was supported by the National Research Foundation of Korea (NRF) project (2015R1D1A3A01020410).

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chifotides, H. T. & Dunbar, K. R. (2013). Acc. Chem. Res. 46, 894–906. Web of Science CrossRef CAS PubMed Google Scholar
Furukawa, S., Reboul, J., Diring, S., Sumida, K. & Kitagawa, S. (2014). Chem. Soc. Rev. 43, 5700–5734. Web of Science CrossRef CAS PubMed Google Scholar
Ju, H., Lee, E., Moon, S.-H., Lee, S. S. & Park, K.-M. (2014). Bull. Korean Chem. Soc. 35, 3658–3660. Web of Science CSD CrossRef CAS Google Scholar
Khlobystov, A. N., Brett, M. T., Blake, A. J., Champness, N. R., Gill, P. M. W., O'Neill, D. P., Teat, S. J., Wilson, C. & Schröder, M. (2003). J. Am. Chem. Soc. 125, 6753–6761. Web of Science CSD CrossRef PubMed CAS Google Scholar
Lee, E., Ju, H., Moon, S.-H., Lee, S. S. & Park, K.-M. (2015). Bull. Korean Chem. Soc. 36, 1532–1535. Web of Science CrossRef CAS Google Scholar
Lee, E., Ryu, H., Moon, S.-H. & Park, K.-M. (2013). Bull. Korean Chem. Soc. 34, 3477–3480. Web of Science CSD CrossRef CAS Google Scholar
Leong, W. L. & Vittal, J. J. (2011). Chem. Rev. 111, 688–764. Web of Science CrossRef CAS PubMed Google Scholar
Matter, H., Nazaré, M., Güssregen, S., Will, D. W., Schreuder, H., Bauer, A., Urmann, M., Ritter, K., Wagner, M. & Wehner, V. (2009). Angew. Chem. Int. Ed. 48, 2911–2916. Web of Science CrossRef CAS Google Scholar
Moon, S.-H., Cho, S. & Park, K.-M. (2014). Acta Cryst. E70, 389–391. CSD CrossRef IUCr Journals Google Scholar
Moon, S.-H., Kang, Y. & Park, K.-M. (2015). Acta Cryst. E71, 1287–1289. Web of Science CSD CrossRef IUCr Journals Google Scholar
Moon, S.-H. & Park, K.-M. (2014). Acta Cryst. E70, m233. CSD CrossRef IUCr Journals Google Scholar
Robson, R. (2008). Dalton Trans. pp. 5113–5131. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Silva, P., Vilela, S. M. F., Tomé, J. P. C. & Almeida Paz, F. A. (2015). Chem. Soc. Rev. 44, 6774–6803. Web of Science CrossRef CAS PubMed Google Scholar
Uemura, K., Kumamoto, Y. & Kitagawa, S. (2008). Chem. Eur. J. 14, 9565–9576. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhang, Z.-Y., Deng, Z.-P., Huo, L.-H., Zhao, H. & Gao, S. (2013). Inorg. Chem. 52, 5914–5923. Web of Science CSD CrossRef CAS PubMed 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.