catena-Poly[[dichloridomercury(II)]-μ-1,4-bis­[(pyridin-2-yl)meth­oxy]benzene-κ2N:N′]

Liu, Y.; Zhang, H.-S.; Hu, M.-X.; Hou, G.-F.; Gao, J.-S.

doi:10.1107/S1600536811038323

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1427

https://doi.org/10.1107/S1600536811038323

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catena-Poly[[dichloridomercury(II)]-μ-1,4-bis[(pyridin-2-yl)methoxy]benzene-κ²N:N′]

Ying Liu,^a ^* Hong-Sen Zhang,^b Ming-Xing Hu,^a Guang-Feng Hou ^c and Jin-Sheng Gao ^c

^aDepartment of Materials and Chemical Engineering, Heilongjiang Institute of Technology, Harbin 150050, People's Republic of China, ^bModern Analysis, Test and Research Center, Heilongjiang Institute of Science and Technology, Harbin 150027, People's Republic of China, and ^cCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 2 September 2011; accepted 19 September 2011; online 30 September 2011)

In the title compound, [HgCl₂(C₁₈H₁₆N₂O₂)]_n, the Hg^II atom is four-coordinated in a distorted tetrahedral environment defined by two Cl atoms and two N atoms from two 1,4-bis(pyridin-2-ylmethoxy)benzene ligands. The ligand shows a non-coplanar conformation, in which the dihedral angles between the two terminal pyridine rings and the linking benzene ring are 7.275 (17) and 74.020 (14)°. The flexible ligands link the Hg^II atoms into a chain running along [010], with an Hg⋯Hg separation of 10.335 (5) Å, which is equal to the b axis. The chains are connected by C—H⋯O and C—H⋯Cl hydrogen bonds.

Related literature

For the synthesis of the ligand and general background to flexible pyridyl-based ligands, see: Liu et al. (2010a ,b ); Wang et al. (2007 ).

Experimental

Crystal data

[HgCl₂(C₁₈H₁₆N₂O₂)]
M_r = 563.82
Triclinic, $[P \overline 1]$
a = 9.201 (5) Å
b = 10.335 (5) Å
c = 11.040 (6) Å
α = 86.11 (2)°
β = 66.51 (2)°
γ = 73.860 (18)°
V = 923.8 (9) Å³
Z = 2
Mo Kα radiation
μ = 8.63 mm⁻¹
T = 293 K
0.19 × 0.17 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.288, T_max = 0.325
9080 measured reflections
4179 independent reflections
3688 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.122
S = 1.16
4179 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 1.56 e Å⁻³
Δρ_min = −1.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl1ⁱ	0.93	2.82	3.692 (8)	157
C11—H11⋯O2ⁱⁱ	0.93	2.51	3.338 (9)	149
Symmetry codes: (i) -x+1, -y+3, -z; (ii) -x, -y+1, -z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811038323/hy2469sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038323/hy2469Isup2.hkl

checkCIF report

Comment top

The metal-organic frameworks are determined by many factors, in which the organic ligands as building blocks and the kinds of metal ions are most important. Many pyridyl-containing ligands with strong coordination ability and functional characteristics have been studied over the recent years (Wang et al., 2007). The flexible bipyridyl ligands can react with transition metals to construct helical-like structures. Recently, as a continuation of previous studies (Liu et al., 2010a, b), we report here the crystal structure of the title compound.

In the title compound, the Hg^II atom is four-coordinated by two Cl atoms and two N atoms from two 1,4-bis(pyridin-2-ylmethoxy)benzene ligands, forming a tetrahedral geometry (Fig. 1). The Hg—Cl bond lengths are 2.398 (2) and 2.452 (2) Å, and Hg—N bond lengths are 2.282 (5) and 2.411 (5) Å. The angles around the Hg atom are in a range of 100.63 (13)–122.30 (12)°. The ligand shows a noncoplanar conformation, in which the dihedral angles between the two terminal pyridine rings and the linking benzene ring are 7.275 (17) and 74.020 (14)°. In the crystal, the flexible ligands link the Hg^II atoms into a chain running along [0 1 0], with an Hg···Hg separation of 10.335 (5)Å, which is equal to the b axis of the unit cell (Fig. 2). The chains are connected by C—H···O and C—H···Cl hydrogen bonds (Table 1).

Related literature top

For the synthesis of the ligand and general background to flexible pyridyl-based ligands, see: Liu et al. (2010a,b); Wang et al. (2007).

Experimental top

1,4-Bis(pyridin-2-ylmethoxy)benzene was synthesized as the literature method (Liu et al., 2010a,b). The title compound was produced by the reaction of ZnCl₂ (0.50 mmol, 0.068 g) in water (5 ml) and 1,4-bis(pyridin-2-ylmethoxy)benzene (0.5 mmol, 0.146 g) in methanol (5 ml) under constant stirring. The mixture was filtered after stirring for about one hour. The filtate was maintained for about one week at room temperature to give colorless block-like crystals suitable for X-ray analysis.

Structure description top

For the synthesis of the ligand and general background to flexible pyridyl-based ligands, see: Liu et al. (2010a,b); Wang et al. (2007).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) x, 1+y, z.]
	Fig. 2. A view of the chain structure along the b axis. H atoms have been omitted for clarity.

catena-Poly[dichlorido{µ-1,4-bis[(pyridin-2-yl)methoxy]benzene-κ²N:N'}mercury(II)] top

Crystal data top

[HgCl₂(C₁₈H₁₆N₂O₂)]	Z = 2
M_r = 563.82	F(000) = 536
Triclinic, P1	D_x = 2.027 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.201 (5) Å	Cell parameters from 8238 reflections
b = 10.335 (5) Å	θ = 3.6–27.5°
c = 11.040 (6) Å	µ = 8.63 mm⁻¹
α = 86.11 (2)°	T = 293 K
β = 66.51 (2)°	Block, colorless
γ = 73.860 (18)°	0.19 × 0.17 × 0.17 mm
V = 923.8 (9) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4179 independent reflections
Radiation source: fine-focus sealed tube	3688 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scan	θ_max = 27.5°, θ_min = 3.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→11
T_min = 0.288, T_max = 0.325	k = −13→13
9080 measured reflections	l = −14→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0627P)²] where P = (F_o² + 2F_c²)/3
4179 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 1.56 e Å⁻³
0 restraints	Δρ_min = −1.74 e Å⁻³

Crystal data top

[HgCl₂(C₁₈H₁₆N₂O₂)]	γ = 73.860 (18)°
M_r = 563.82	V = 923.8 (9) Å³
Triclinic, P1	Z = 2
a = 9.201 (5) Å	Mo Kα radiation
b = 10.335 (5) Å	µ = 8.63 mm⁻¹
c = 11.040 (6) Å	T = 293 K
α = 86.11 (2)°	0.19 × 0.17 × 0.17 mm
β = 66.51 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4179 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3688 reflections with I > 2σ(I)
T_min = 0.288, T_max = 0.325	R_int = 0.051
9080 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.16	Δρ_max = 1.56 e Å⁻³
4179 reflections	Δρ_min = −1.74 e Å⁻³
226 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.3961 (8)	1.3384 (6)	0.0220 (7)	0.0444 (16)
H1	0.3896	1.4124	0.0692	0.053*
C2	0.5080 (10)	1.3141 (7)	−0.1062 (7)	0.0503 (18)
H2	0.5756	1.3705	−0.1448	0.060*
C3	0.5187 (9)	1.2054 (7)	−0.1767 (7)	0.0505 (18)
H3	0.5939	1.1867	−0.2640	0.061*
C4	0.4164 (9)	1.1238 (7)	−0.1164 (7)	0.0438 (15)
H4	0.4213	1.0497	−0.1626	0.053*
C5	0.3057 (8)	1.1542 (6)	0.0148 (6)	0.0343 (12)
C6	0.1907 (9)	1.0703 (6)	0.0877 (7)	0.0414 (15)
H6A	0.2040	1.0418	0.1691	0.050*
H6B	0.0774	1.1229	0.1100	0.050*
C7	0.1385 (9)	0.8632 (6)	0.0600 (6)	0.0370 (14)
C8	0.0193 (9)	0.8735 (6)	0.1867 (7)	0.0468 (18)
H8	−0.0110	0.9494	0.2412	0.056*
C9	−0.0548 (9)	0.7707 (6)	0.2322 (7)	0.0444 (16)
H9	−0.1340	0.7771	0.3181	0.053*
C10	−0.0126 (8)	0.6587 (5)	0.1515 (6)	0.0321 (12)
C11	0.1058 (9)	0.6489 (6)	0.0227 (6)	0.0407 (15)
H11	0.1345	0.5739	−0.0326	0.049*
C12	0.1794 (9)	0.7515 (7)	−0.0215 (7)	0.0446 (16)
H12	0.2580	0.7457	−0.1076	0.053*
C13	−0.1985 (8)	0.5549 (6)	0.3153 (6)	0.0374 (13)
H13A	−0.2948	0.6272	0.3208	0.045*
H13B	−0.1615	0.5746	0.3811	0.045*
C14	−0.2419 (7)	0.4243 (6)	0.3415 (6)	0.0324 (12)
C15	−0.3957 (8)	0.4143 (7)	0.3561 (7)	0.0401 (14)
H15	−0.4710	0.4882	0.3417	0.048*
C16	−0.4359 (8)	0.2947 (7)	0.3918 (7)	0.0415 (15)
H16	−0.5389	0.2874	0.4030	0.050*
C17	−0.3210 (8)	0.1850 (6)	0.4111 (7)	0.0413 (15)
H17	−0.3447	0.1027	0.4339	0.050*
C18	−0.1700 (8)	0.2013 (6)	0.3954 (7)	0.0396 (14)
H18	−0.0937	0.1290	0.4106	0.048*
Cl1	0.2047 (2)	1.51507 (16)	0.35012 (17)	0.0436 (4)
Cl2	0.2358 (3)	1.10739 (19)	0.4104 (2)	0.0581 (5)
Hg1	0.13517 (3)	1.31748 (2)	0.31567 (2)	0.04162 (12)
N1	0.2955 (6)	1.2612 (5)	0.0831 (5)	0.0361 (11)
N2	−0.1291 (6)	0.3179 (5)	0.3590 (5)	0.0328 (11)
O1	0.2274 (7)	0.9563 (5)	0.0059 (5)	0.0490 (13)
O2	−0.0724 (6)	0.5467 (4)	0.1880 (5)	0.0450 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.046 (4)	0.033 (3)	0.047 (4)	−0.016 (3)	−0.007 (3)	−0.005 (3)
C2	0.056 (4)	0.044 (3)	0.045 (4)	−0.027 (3)	−0.006 (3)	0.006 (3)
C3	0.048 (4)	0.051 (4)	0.042 (4)	−0.016 (3)	−0.007 (3)	0.006 (3)
C4	0.055 (4)	0.041 (3)	0.044 (4)	−0.023 (3)	−0.022 (3)	0.005 (3)
C5	0.039 (3)	0.028 (3)	0.043 (3)	−0.014 (2)	−0.022 (3)	0.008 (2)
C6	0.055 (4)	0.035 (3)	0.044 (3)	−0.025 (3)	−0.021 (3)	0.005 (3)
C7	0.052 (4)	0.029 (3)	0.035 (3)	−0.018 (3)	−0.019 (3)	0.004 (2)
C8	0.052 (4)	0.029 (3)	0.040 (3)	−0.011 (3)	0.004 (3)	−0.015 (3)
C9	0.049 (4)	0.036 (3)	0.041 (3)	−0.019 (3)	−0.006 (3)	−0.003 (3)
C10	0.041 (3)	0.026 (2)	0.031 (3)	−0.009 (2)	−0.016 (2)	−0.005 (2)
C11	0.059 (4)	0.034 (3)	0.029 (3)	−0.018 (3)	−0.012 (3)	−0.009 (2)
C12	0.061 (4)	0.049 (4)	0.031 (3)	−0.028 (3)	−0.017 (3)	0.005 (3)
C13	0.043 (3)	0.030 (3)	0.039 (3)	−0.013 (3)	−0.014 (3)	0.006 (2)
C14	0.037 (3)	0.030 (3)	0.025 (3)	−0.006 (2)	−0.008 (2)	−0.002 (2)
C15	0.034 (3)	0.046 (3)	0.047 (4)	−0.018 (3)	−0.020 (3)	0.011 (3)
C16	0.036 (3)	0.044 (3)	0.044 (3)	−0.017 (3)	−0.010 (3)	−0.004 (3)
C17	0.041 (3)	0.040 (3)	0.044 (3)	−0.022 (3)	−0.011 (3)	0.005 (3)
C18	0.040 (3)	0.029 (3)	0.043 (3)	−0.008 (3)	−0.011 (3)	0.003 (3)
Cl1	0.0489 (8)	0.0469 (8)	0.0472 (9)	−0.0256 (7)	−0.0236 (7)	0.0053 (7)
Cl2	0.0738 (12)	0.0447 (9)	0.0561 (11)	−0.0065 (9)	−0.0337 (10)	0.0111 (8)
Hg1	0.04200 (17)	0.04003 (17)	0.05152 (19)	−0.01992 (12)	−0.02262 (13)	0.00908 (12)
N1	0.039 (3)	0.028 (2)	0.038 (3)	−0.011 (2)	−0.011 (2)	0.002 (2)
N2	0.035 (2)	0.030 (2)	0.035 (3)	−0.012 (2)	−0.014 (2)	0.001 (2)
O1	0.070 (3)	0.042 (2)	0.038 (2)	−0.034 (2)	−0.012 (2)	0.001 (2)
O2	0.063 (3)	0.040 (2)	0.038 (2)	−0.031 (2)	−0.015 (2)	0.0025 (19)

Geometric parameters (Å, º) top

C1—N1	1.338 (8)	C10—C11	1.393 (8)
C1—C2	1.367 (9)	C11—C12	1.374 (9)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.369 (10)	C12—H12	0.9300
C2—H2	0.9300	C13—O2	1.410 (8)
C3—C4	1.380 (9)	C13—C14	1.491 (8)
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.393 (9)	C13—H13B	0.9700
C4—H4	0.9300	C14—N2	1.349 (8)
C5—N1	1.341 (8)	C14—C15	1.391 (9)
C5—C6	1.502 (8)	C15—C16	1.375 (9)
C6—O1	1.413 (7)	C15—H15	0.9300
C6—H6A	0.9700	C16—C17	1.389 (10)
C6—H6B	0.9700	C16—H16	0.9300
C7—C8	1.380 (9)	C17—C18	1.387 (9)
C7—C12	1.383 (9)	C17—H17	0.9300
C7—O1	1.386 (7)	C18—N2	1.349 (8)
C8—C9	1.379 (9)	C18—H18	0.9300
C8—H8	0.9300	Hg1—Cl1	2.3981 (18)
C9—C10	1.378 (8)	Hg1—Cl2	2.452 (2)
C9—H9	0.9300	Hg1—N2ⁱ	2.282 (5)
C10—O2	1.385 (7)	Hg1—N1	2.411 (5)

N1—C1—C2	123.4 (6)	C11—C12—H12	119.5
N1—C1—H1	118.3	C7—C12—H12	119.5
C2—C1—H1	118.3	O2—C13—C14	109.4 (5)
C1—C2—C3	118.8 (6)	O2—C13—H13A	109.8
C1—C2—H2	120.6	C14—C13—H13A	109.8
C3—C2—H2	120.6	O2—C13—H13B	109.8
C2—C3—C4	119.1 (6)	C14—C13—H13B	109.8
C2—C3—H3	120.4	H13A—C13—H13B	108.3
C4—C3—H3	120.4	N2—C14—C15	121.4 (6)
C3—C4—C5	119.0 (6)	N2—C14—C13	116.8 (6)
C3—C4—H4	120.5	C15—C14—C13	121.6 (6)
C5—C4—H4	120.5	C16—C15—C14	119.7 (6)
N1—C5—C4	121.6 (6)	C16—C15—H15	120.1
N1—C5—C6	116.1 (5)	C14—C15—H15	120.1
C4—C5—C6	122.3 (6)	C15—C16—C17	119.3 (6)
O1—C6—C5	108.7 (5)	C15—C16—H16	120.3
O1—C6—H6A	109.9	C17—C16—H16	120.3
C5—C6—H6A	109.9	C18—C17—C16	118.2 (6)
O1—C6—H6B	109.9	C18—C17—H17	120.9
C5—C6—H6B	109.9	C16—C17—H17	120.9
H6A—C6—H6B	108.3	N2—C18—C17	122.7 (6)
C8—C7—C12	119.7 (6)	N2—C18—H18	118.6
C8—C7—O1	124.9 (5)	C17—C18—H18	118.6
C12—C7—O1	115.4 (6)	N2ⁱ—Hg1—Cl1	122.30 (12)
C9—C8—C7	119.8 (5)	N2ⁱ—Hg1—N1	107.69 (19)
C9—C8—H8	120.1	Cl1—Hg1—N1	102.88 (13)
C7—C8—H8	120.1	N2ⁱ—Hg1—Cl2	102.39 (14)
C10—C9—C8	120.6 (6)	Cl1—Hg1—Cl2	118.53 (8)
C10—C9—H9	119.7	N1—Hg1—Cl2	100.63 (13)
C8—C9—H9	119.7	C1—N1—C5	118.0 (5)
C9—C10—O2	125.7 (5)	C1—N1—Hg1	114.8 (4)
C9—C10—C11	119.9 (5)	C5—N1—Hg1	126.7 (4)
O2—C10—C11	114.3 (5)	C14—N2—C18	118.6 (5)
C12—C11—C10	119.1 (5)	C14—N2—Hg1ⁱⁱ	123.9 (4)
C12—C11—H11	120.4	C18—N2—Hg1ⁱⁱ	117.3 (4)
C10—C11—H11	120.4	C7—O1—C6	116.8 (5)
C11—C12—C7	121.0 (6)	C10—O2—C13	116.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1ⁱⁱⁱ	0.93	2.82	3.692 (8)	157
C11—H11···O2^iv	0.93	2.51	3.338 (9)	149

Symmetry codes: (iii) −x+1, −y+3, −z; (iv) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[HgCl₂(C₁₈H₁₆N₂O₂)]
M_r	563.82
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.201 (5), 10.335 (5), 11.040 (6)
α, β, γ (°)	86.11 (2), 66.51 (2), 73.860 (18)
V (Å³)	923.8 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	8.63
Crystal size (mm)	0.19 × 0.17 × 0.17

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.288, 0.325
No. of measured, independent and observed [I > 2σ(I)] reflections	9080, 4179, 3688
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.122, 1.16
No. of reflections	4179
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.56, −1.74

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1ⁱ	0.93	2.82	3.692 (8)	157
C11—H11···O2ⁱⁱ	0.93	2.51	3.338 (9)	149

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

Acknowledgements

The authors thank the Project of the Educational Commission of Heilongjiang Province of China (No. 12511472), Heilongjiang Institute of Technology and Heilongjiang University for supporting this work.

References

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