Bis((E)-2-{5,5-di­methyl-3-[4-(1H-1,2,4-triazol-1-yl-κN4)styr­yl]cyclo­hex-2-enyl­idene}malono­nitrile)­diiodido­mercury(II)

Wang, L.-K.; Zhu, W.-J.; Zhou, H.-P.

doi:10.1107/S160053681302518X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 10| October 2013| Pages m556-m557

doi:10.1107/S160053681302518X

Open

access

Bis((E)-2-{5,5-dimethyl-3-[4-(1H-1,2,4-triazol-1-yl-κN⁴)styryl]cyclohex-2-enylidene}malononitrile)diiodidomercury(II)

Lian-Ke Wang,^a Wei-Ju Zhu ^a and Hong-Ping Zhou ^a ^*

^aDeparment of Chemistry, Anhui University, Hefei 230039, People's Republic of China and Key Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: zhpzhp@263.net

(Received 29 July 2013; accepted 11 September 2013; online 21 September 2013)

In the title complex, [HgI₂(C₂₁H₁₉N₅)₂], the Hg^II ion is located on a twofold rotation axis and is coordinated by two I atoms and two N atoms from two (E)-2-{5,5-dimethyl-3-[4-(1H-1,2,4-triazol-1-yl)styryl]cyclohex-2-enylidene}malononitrile ligands in a distorted tetrahedral geometry. In the crystal, the molecules are linked by intermolecular π–π interactions between the triazole and benzene rings [centroid–centroid distance = 3.794 (3) Å] into a band extending in [010]. These bands are further connected by C—H⋯N hydrogen bonds into a two-dimensional network parallel to (100).

CCDC reference: 948299

Related literature

For background to metal-organic complexes, see: Haneda et al. (2007 ); Li et al. (2006 ); Liu et al. (2010 , 2011 ); Satapathy et al. (2012 ); Sun et al. (2012 ). For the organic ligand of the title compound, see: Zheng et al. (2013 ). For related structures, see: Jin, Wang et al. (2013 ); Jin, Zhang et al. (2013 ); Zhou et al. (2009 ).

Experimental

Crystal data

[HgI₂(C₂₁H₁₉N₅)₂]
M_r = 1137.21
Monoclinic, C 2/c
a = 38.9622 (16) Å
b = 5.5684 (12) Å
c = 21.9564 (14) Å
β = 117.738 (2)°
V = 4216.2 (10) Å³
Z = 4
Mo Kα radiation
μ = 5.16 mm⁻¹
T = 291 K
0.30 × 0.20 × 0.18 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.307, T_max = 0.457
14961 measured reflections
4078 independent reflections
3384 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.071
S = 1.01
4078 reflections
251 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯N2ⁱ	0.93	2.48	3.354 (7)	157
Symmetry code: (i) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 948299

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S160053681302518X/hy2634sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681302518X/hy2634Isup2.hkl

checkCIF report

Comment top

The design and synthesis of metal-organic hybrid complexes based on strong coordinate bonds and multiple weak non-covalent forces have become one of the most active fields in coordination chemistry and crystal engineering not only for their fascinating structural features but also for their interesting properties as new functional materials with tremendous potential applications in the areas of luminescence, catalysis, separation, adsorption, biological chemistry (Haneda et al., 2007; Li et al., 2006; Liu et al., 2010, 2011; Satapathy et al., 2012; Sun et al., 2012). The organic ligand of the title compound had been investigated for its optical properties (Zheng et al., 2013). A variety of mercury(II) complexes have been reported (Jin, Wang et al., 2013). Besides, triazole and isophorone-malononitrile complexes have been reported (Jin, Zhang et al., 2013; Zhou et al., 2009). In this paper, we report the synthesis and crystal structure of the title complex (Fig. 1). In the crystal, intermolecular π–π interactions between the triazole and benzene rings [centroid–centroid distance = 3.794 (3) Å] link the molecules into a band extending in [010] (Fig. 2). The neighboring bands are further linked into a two-dimensional network parallel to (100) through C—H···N hydrogen bonds (Fig.3).

Related literature top

For background to metal-organic complexes, see: Haneda et al. (2007); Li et al. (2006); Liu et al. (2010, 2011); Satapathy et al. (2012); Sun et al. (2012). For the organic ligand of the title compound, see: Zheng et al. (2013). For related structures, see: Jin, Wang et al. (2013); Jin, Zhang et al. (2013); Zhou et al. (2009).

Experimental top

For the preparation of the title complex, (E)-2-(3-(4-(1H-1,2,4-triazol-1-yl)styryl)- 5,5-dimethylcyclohex-2-enylidene)malononitrile (0.341 g, 1 mmol) in 25 ml of dichloromethane was added into a 50 ml colorimeter tube, carefully layered with a clear acetonitrile and benzene solution (25 ml) of HgI₂ (0.227 g, 0.5 mmol). Crystals were obtained by slow interlayer diffusion (yield: 0.427 g, 75.1%).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) -x, y, 3/2-z.]
	Fig. 2. The one-dimensional structure of the title complex, showing π–π interactions (dashed lines).
	Fig. 3. The two-dimensional structure of the title complex, showing C—H···N hydrogen bonds (dashed lines).

Bis((E)-2-{5,5-dimethyl-3-[4-(1H-1,2,4-triazol-1-yl-κN⁴)styryl]cyclohex-2-enylidene}malononitrile)diiodidomercury(II) top

Crystal data top

[HgI₂(C₂₁H₁₉N₅)₂]	F(000) = 2184
M_r = 1137.21	D_x = 1.792 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 38.9622 (16) Å	Cell parameters from 3126 reflections
b = 5.5684 (12) Å	θ = 2.1–23.6°
c = 21.9564 (14) Å	µ = 5.16 mm⁻¹
β = 117.738 (2)°	T = 291 K
V = 4216.2 (10) Å³	Needle, yellow
Z = 4	0.30 × 0.20 × 0.18 mm

Data collection top

Bruker APEX CCD diffractometer	4078 independent reflections
Radiation source: fine-focus sealed tube	3384 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −47→47
T_min = 0.307, T_max = 0.457	k = −6→6
14961 measured reflections	l = −26→26

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.04P)² + 0.22P] where P = (F_o² + 2F_c²)/3
4078 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[HgI₂(C₂₁H₁₉N₅)₂]	V = 4216.2 (10) Å³
M_r = 1137.21	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 38.9622 (16) Å	µ = 5.16 mm⁻¹
b = 5.5684 (12) Å	T = 291 K
c = 21.9564 (14) Å	0.30 × 0.20 × 0.18 mm
β = 117.738 (2)°

Data collection top

Bruker APEX CCD diffractometer	4078 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3384 reflections with I > 2σ(I)
T_min = 0.307, T_max = 0.457	R_int = 0.032
14961 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.01	Δρ_max = 0.78 e Å⁻³
4078 reflections	Δρ_min = −0.52 e Å⁻³
251 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.

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

	x	y	z	U_iso*/U_eq
Hg1	0.0000	1.49817 (4)	0.7500	0.04679 (9)
I1	0.06739 (2)	1.65983 (6)	0.84809 (2)	0.06479 (11)
C19	0.11064 (13)	0.4748 (8)	0.6784 (2)	0.0541 (11)
H19	0.1329	0.4209	0.7164	0.065*
C15	0.06588 (13)	0.4500 (8)	0.5599 (2)	0.0560 (11)
H15	0.0575	0.3788	0.5170	0.067*
C16	0.04479 (12)	0.6381 (8)	0.5667 (2)	0.0540 (10)
H16	0.0227	0.6937	0.5288	0.065*
N5	0.01215 (9)	1.2154 (6)	0.67843 (16)	0.0452 (7)
N3	0.03392 (9)	0.9312 (6)	0.63805 (16)	0.0409 (7)
C13	0.12305 (12)	0.1699 (7)	0.6110 (2)	0.0485 (9)
H13	0.1406	0.1013	0.6525	0.058*
C21	−0.01308 (12)	1.1596 (8)	0.6130 (2)	0.0590 (11)
H21	−0.0370	1.2354	0.5892	0.071*
C20	0.04150 (12)	1.0708 (7)	0.6927 (2)	0.0447 (9)
H20	0.0641	1.0659	0.7344	0.054*
C17	0.05698 (10)	0.7431 (6)	0.63072 (19)	0.0401 (8)
C14	0.09914 (11)	0.3646 (7)	0.6153 (2)	0.0439 (9)
N4	−0.00144 (11)	0.9900 (6)	0.58534 (19)	0.0614 (10)
C18	0.08964 (12)	0.6650 (8)	0.6862 (2)	0.0528 (10)
H18	0.0979	0.7374	0.7290	0.063*
C10	0.14855 (11)	−0.1065 (7)	0.5526 (2)	0.0430 (9)
C9	0.17746 (11)	−0.2203 (7)	0.61823 (19)	0.0481 (9)
H9A	0.1640	−0.3332	0.6333	0.058*
H9B	0.1885	−0.0966	0.6532	0.058*
C11	0.14662 (11)	−0.1692 (7)	0.4915 (2)	0.0468 (9)
H11	0.1295	−0.0878	0.4520	0.056*
C12	0.12256 (12)	0.0798 (7)	0.5548 (2)	0.0490 (10)
H12	0.1040	0.1402	0.5129	0.059*
C6	0.21068 (11)	−0.3527 (6)	0.61357 (19)	0.0451 (9)
C5	0.19376 (13)	−0.5051 (6)	0.5484 (2)	0.0504 (10)
H5A	0.2147	−0.5826	0.5437	0.061*
H5B	0.1775	−0.6298	0.5524	0.061*
C4	0.17029 (11)	−0.3582 (7)	0.4857 (2)	0.0448 (9)
C1	0.19109 (13)	−0.6083 (9)	0.4172 (2)	0.0556 (10)
C2	0.17018 (12)	−0.4045 (8)	0.4249 (2)	0.0493 (10)
C3	0.14937 (13)	−0.2621 (9)	0.3649 (2)	0.0566 (11)
N2	0.13295 (13)	−0.1425 (8)	0.3170 (2)	0.0772 (12)
N1	0.20731 (13)	−0.7689 (8)	0.4121 (2)	0.0824 (13)
C8	0.24041 (12)	−0.1776 (7)	0.6121 (2)	0.0580 (11)
H8A	0.2609	−0.2658	0.6095	0.087*
H8B	0.2510	−0.0819	0.6531	0.087*
H8C	0.2280	−0.0748	0.5726	0.087*
C7	0.23118 (16)	−0.5185 (7)	0.6758 (3)	0.0698 (14)
H7A	0.2131	−0.6351	0.6761	0.105*
H7B	0.2411	−0.4252	0.7173	0.105*
H7C	0.2522	−0.5992	0.6732	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.05187 (14)	0.04752 (14)	0.04360 (14)	0.000	0.02444 (11)	0.000
I1	0.0631 (2)	0.0737 (2)	0.05467 (19)	−0.01842 (15)	0.02500 (15)	−0.00968 (15)
C19	0.056 (3)	0.069 (3)	0.043 (2)	0.019 (2)	0.027 (2)	0.012 (2)
C15	0.053 (3)	0.064 (3)	0.050 (3)	0.000 (2)	0.023 (2)	−0.023 (2)
C16	0.044 (2)	0.066 (3)	0.046 (2)	0.008 (2)	0.0154 (18)	−0.016 (2)
N5	0.0489 (19)	0.0457 (18)	0.0442 (18)	0.0023 (15)	0.0242 (16)	−0.0050 (15)
N3	0.0427 (18)	0.0461 (17)	0.0376 (17)	0.0000 (14)	0.0219 (15)	−0.0028 (14)
C13	0.056 (2)	0.045 (2)	0.053 (2)	0.0027 (18)	0.032 (2)	0.0038 (19)
C21	0.048 (2)	0.077 (3)	0.048 (2)	0.014 (2)	0.019 (2)	−0.007 (2)
C20	0.049 (2)	0.047 (2)	0.039 (2)	0.0000 (18)	0.0210 (18)	−0.0038 (17)
C17	0.046 (2)	0.0409 (19)	0.043 (2)	−0.0022 (17)	0.0285 (18)	−0.0026 (17)
C14	0.049 (2)	0.045 (2)	0.049 (2)	−0.0011 (18)	0.0314 (19)	−0.0004 (18)
N4	0.050 (2)	0.082 (3)	0.044 (2)	0.0147 (18)	0.0156 (17)	−0.0155 (18)
C18	0.064 (3)	0.065 (3)	0.035 (2)	0.016 (2)	0.028 (2)	−0.001 (2)
C10	0.047 (2)	0.0361 (19)	0.051 (2)	−0.0018 (17)	0.0268 (19)	−0.0027 (18)
C9	0.057 (2)	0.041 (2)	0.051 (2)	−0.0002 (18)	0.029 (2)	−0.0021 (19)
C11	0.050 (2)	0.045 (2)	0.045 (2)	0.0068 (18)	0.0219 (19)	−0.0007 (18)
C12	0.048 (2)	0.048 (2)	0.055 (3)	0.0043 (19)	0.027 (2)	−0.004 (2)
C6	0.055 (2)	0.0315 (19)	0.045 (2)	0.0024 (17)	0.0202 (18)	0.0003 (17)
C5	0.061 (3)	0.032 (2)	0.061 (3)	0.0023 (18)	0.031 (2)	−0.0009 (19)
C4	0.042 (2)	0.042 (2)	0.053 (2)	−0.0049 (17)	0.0240 (18)	−0.0077 (18)
C1	0.056 (3)	0.056 (3)	0.060 (3)	−0.002 (2)	0.031 (2)	−0.014 (2)
C2	0.047 (2)	0.045 (2)	0.054 (3)	−0.0012 (19)	0.023 (2)	−0.012 (2)
C3	0.053 (3)	0.070 (3)	0.045 (3)	0.000 (2)	0.021 (2)	−0.018 (2)
N2	0.081 (3)	0.087 (3)	0.055 (3)	0.007 (2)	0.024 (2)	−0.007 (2)
N1	0.082 (3)	0.075 (3)	0.103 (3)	0.003 (2)	0.053 (3)	−0.028 (3)
C8	0.051 (2)	0.047 (2)	0.071 (3)	−0.0008 (19)	0.024 (2)	−0.002 (2)
C7	0.091 (4)	0.048 (3)	0.062 (3)	0.014 (2)	0.028 (3)	0.009 (2)

Geometric parameters (Å, º) top

Hg1—N5	2.422 (3)	C10—C9	1.495 (5)
Hg1—I1	2.6606 (8)	C9—C6	1.533 (5)
C19—C14	1.385 (6)	C9—H9A	0.9700
C19—C18	1.397 (5)	C9—H9B	0.9700
C19—H19	0.9300	C11—C4	1.444 (5)
C15—C16	1.381 (5)	C11—H11	0.9300
C15—C14	1.384 (6)	C12—H12	0.9300
C15—H15	0.9300	C6—C5	1.524 (5)
C16—C17	1.386 (5)	C6—C8	1.526 (5)
C16—H16	0.9300	C6—C7	1.531 (6)
N5—C20	1.312 (5)	C5—C4	1.494 (6)
N5—C21	1.346 (5)	C5—H5A	0.9700
N3—C20	1.342 (5)	C5—H5B	0.9700
N3—N4	1.364 (5)	C4—C2	1.357 (5)
N3—C17	1.437 (5)	C1—N1	1.131 (5)
C13—C12	1.324 (5)	C1—C2	1.452 (6)
C13—C14	1.461 (5)	C2—C3	1.424 (6)
C13—H13	0.9300	C3—N2	1.153 (5)
C21—N4	1.313 (5)	C8—H8A	0.9600
C21—H21	0.9300	C8—H8B	0.9600
C20—H20	0.9300	C8—H8C	0.9600
C17—C18	1.360 (5)	C7—H7A	0.9600
C18—H18	0.9300	C7—H7B	0.9600
C10—C11	1.354 (5)	C7—H7C	0.9600
C10—C12	1.466 (5)

N5ⁱ—Hg1—N5	98.89 (15)	C10—C9—H9A	108.6
N5ⁱ—Hg1—I1	96.43 (8)	C6—C9—H9A	108.6
N5—Hg1—I1	109.14 (7)	C10—C9—H9B	108.6
N5ⁱ—Hg1—I1ⁱ	109.15 (7)	C6—C9—H9B	108.6
N5—Hg1—I1ⁱ	96.43 (8)	H9A—C9—H9B	107.5
I1—Hg1—I1ⁱ	140.450 (19)	C10—C11—C4	122.2 (4)
C14—C19—C18	121.6 (4)	C10—C11—H11	118.9
C14—C19—H19	119.2	C4—C11—H11	118.9
C18—C19—H19	119.2	C13—C12—C10	126.0 (4)
C16—C15—C14	121.7 (4)	C13—C12—H12	117.0
C16—C15—H15	119.1	C10—C12—H12	117.0
C14—C15—H15	119.1	C5—C6—C8	109.7 (3)
C15—C16—C17	119.3 (4)	C5—C6—C7	108.7 (3)
C15—C16—H16	120.4	C8—C6—C7	108.6 (4)
C17—C16—H16	120.4	C5—C6—C9	108.7 (3)
C20—N5—C21	103.6 (3)	C8—C6—C9	111.5 (3)
C20—N5—Hg1	131.0 (3)	C7—C6—C9	109.6 (4)
C21—N5—Hg1	125.2 (3)	C4—C5—C6	111.9 (3)
C20—N3—N4	109.6 (3)	C4—C5—H5A	109.2
C20—N3—C17	129.3 (3)	C6—C5—H5A	109.2
N4—N3—C17	121.1 (3)	C4—C5—H5B	109.2
C12—C13—C14	127.5 (4)	C6—C5—H5B	109.2
C12—C13—H13	116.3	H5A—C5—H5B	107.9
C14—C13—H13	116.3	C2—C4—C11	121.1 (4)
N4—C21—N5	115.0 (4)	C2—C4—C5	121.6 (4)
N4—C21—H21	122.5	C11—C4—C5	117.3 (3)
N5—C21—H21	122.5	N1—C1—C2	178.8 (5)
N5—C20—N3	109.7 (4)	C4—C2—C3	122.9 (4)
N5—C20—H20	125.1	C4—C2—C1	121.2 (4)
N3—C20—H20	125.1	C3—C2—C1	115.9 (4)
C18—C17—C16	120.7 (3)	N2—C3—C2	178.6 (5)
C18—C17—N3	120.3 (3)	C6—C8—H8A	109.5
C16—C17—N3	119.0 (3)	C6—C8—H8B	109.5
C15—C14—C19	117.5 (3)	H8A—C8—H8B	109.5
C15—C14—C13	124.2 (4)	C6—C8—H8C	109.5
C19—C14—C13	118.3 (4)	H8A—C8—H8C	109.5
C21—N4—N3	102.1 (3)	H8B—C8—H8C	109.5
C17—C18—C19	119.2 (4)	C6—C7—H7A	109.5
C17—C18—H18	120.4	C6—C7—H7B	109.5
C19—C18—H18	120.4	H7A—C7—H7B	109.5
C11—C10—C12	119.6 (4)	C6—C7—H7C	109.5
C11—C10—C9	121.0 (3)	H7A—C7—H7C	109.5
C12—C10—C9	119.4 (3)	H7B—C7—H7C	109.5
C10—C9—C6	114.9 (3)

C14—C15—C16—C17	−0.6 (7)	N3—C17—C18—C19	177.2 (3)
C20—N5—C21—N4	−0.1 (5)	C14—C19—C18—C17	0.4 (6)
Hg1—N5—C21—N4	−175.7 (3)	C11—C10—C9—C6	16.2 (5)
C21—N5—C20—N3	−0.8 (4)	C12—C10—C9—C6	−162.3 (3)
Hg1—N5—C20—N3	174.5 (2)	C12—C10—C11—C4	−177.3 (4)
N4—N3—C20—N5	1.4 (5)	C9—C10—C11—C4	4.1 (6)
C17—N3—C20—N5	−178.0 (3)	C14—C13—C12—C10	176.2 (4)
C15—C16—C17—C18	1.0 (6)	C11—C10—C12—C13	−175.1 (4)
C15—C16—C17—N3	−177.2 (4)	C9—C10—C12—C13	3.4 (6)
C20—N3—C17—C18	8.1 (6)	C10—C9—C6—C5	−45.2 (4)
N4—N3—C17—C18	−171.2 (4)	C10—C9—C6—C8	75.8 (4)
C20—N3—C17—C16	−173.8 (4)	C10—C9—C6—C7	−163.9 (4)
N4—N3—C17—C16	6.9 (5)	C8—C6—C5—C4	−66.4 (4)
C16—C15—C14—C19	0.1 (6)	C7—C6—C5—C4	175.1 (4)
C16—C15—C14—C13	−178.7 (4)	C9—C6—C5—C4	55.8 (4)
C18—C19—C14—C15	0.0 (6)	C10—C11—C4—C2	−174.5 (4)
C18—C19—C14—C13	178.9 (4)	C10—C11—C4—C5	7.5 (6)
C12—C13—C14—C15	15.6 (7)	C6—C5—C4—C2	143.5 (4)
C12—C13—C14—C19	−163.3 (4)	C6—C5—C4—C11	−38.5 (5)
N5—C21—N4—N3	0.9 (5)	C11—C4—C2—C3	4.7 (6)
C20—N3—N4—C21	−1.3 (4)	C5—C4—C2—C3	−177.4 (4)
C17—N3—N4—C21	178.1 (3)	C11—C4—C2—C1	−174.2 (4)
C16—C17—C18—C19	−0.9 (6)	C5—C4—C2—C1	3.7 (6)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N2ⁱⁱ	0.93	2.48	3.354 (7)	157

Symmetry code: (ii) x, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N2ⁱ	0.93	2.48	3.354 (7)	157

Symmetry code: (i) x, −y+1, z+1/2.

Acknowledgements

This work was supported by the Program for New Century Excellent Talents in Universities (China), the Doctoral Program Foundation of the Ministry of Education of China (grant No. 20113401110004), the National Natural Science Foundation of China (grant Nos. 21271003 and 21271004), the Natural Science Foundation of the Education Committee of Anhui Province (grant No. KJ2012A024), the Natural Science Foundation of Anhui Province (grant No. 1208085MB22) and the 211 Project of Anhui University.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Haneda, S., Gan, Z. B., Eda, K. & Hayashi, M. (2007). Organometallics, 26, 6551–6555. Web of Science CSD CrossRef CAS Google Scholar
Jin, F., Wang, H.-Z., Zhang, Y., Wang, Y., Zhang, J., Kong, L., Hao, F.-Y., Yang, J.-X., Wu, J.-Y., Tian, Y.-P. & Zhou, H.-P. (2013). CrystEngComm, 15, 3687–3695. Web of Science CSD CrossRef CAS Google Scholar
Jin, F., Zhang, Y., Wang, H.-Z., Zhu, H.-Z., Yan, Y., Zhang, J., Wu, J.-Y., Tian, Y.-P. & Zhou, H.-P. (2013). Cryst. Growth Des. 13, 1978–1987. Web of Science CSD CrossRef CAS Google Scholar
Li, Y.-Y., Lin, C.-K., Zheng, G.-L., Cheng, Z.-Y., You, H., Wang, W.-D. & Lin, J. (2006). Chem. Mater. 18, 3463–3469. Web of Science CSD CrossRef CAS Google Scholar
Liu, Q.-K., Ma, J.-P. & Dong, Y.-B. (2010). J. Am. Chem. Soc. 132, 7005–7017. Web of Science CSD CrossRef CAS PubMed Google Scholar
Liu, Q.-K., Ma, J.-P. & Dong, Y.-B. (2011). Chem. Commun. 47, 12343–12345. Web of Science CSD CrossRef CAS Google Scholar
Satapathy, R., Wu, Y. H. & Lin, H. C. (2012). Org. Lett. 14, 2564–2567. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, L., Li, G.-Z., Xu, M.-H., Li, X.-J., Li, J. R. & Deng, H. (2012). Eur. J. Inorg. Chem. pp. 1764–1772. Web of Science CSD CrossRef Google Scholar
Zheng, Z., Yu, Z.-P., Yang, M.-D., Jin, F., Zhang, Q., Zhou, H.-P., Wu, J.-Y. & Tian, Y.-P. (2013). J. Org. Chem. 78, 3222–3234. Web of Science CSD CrossRef CAS PubMed Google Scholar
Zhou, H.-P., Yin, J.-H., Zheng, L.-X., Wang, P., Hao, F.-Y., Geng, W.-Q., Gan, X.-P., Xu, G.-Y., Wu, J.-Y., Tian, Y.-P., Tao, X.-T., Jiang, M.-H. & Kan, Y.-H. (2009). Cryst. Growth Des. 9, 3789–3798. Web of Science CSD CrossRef CAS 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.