Bis(4-{2-[4-(diethyl­amino)­phen­yl]ethen­yl}pyridine-κN)diiodidozinc

Nie, C.-Y.; Tian, Y.-P.

doi:10.1107/S1600536813001736

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page m135

doi:10.1107/S1600536813001736

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Bis(4-{2-[4-(diethylamino)phenyl]ethenyl}pyridine-κN)diiodidozinc

Cui-Yun Nie ^a,^b and Yu-Peng Tian ^a,^b ^*

^aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and ^bKey Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: yptian@ahu.edu.cn

(Received 23 November 2012; accepted 17 January 2013; online 2 February 2013)

In the title compound, [ZnI₂(C₁₇H₂₀N₂)₂], the Zn^II atom is four-coordinated by two I atoms and the N atoms of two pyridine rings belonging to different ligands in a distorted tetrahedral geometry. The coordinating pyridine rings are oriented in an almost perpendicular fashion, making a dihedral angle of 83.7 (5)°.

Related literature

For the crystal structures of Zn complexes with related pyridine derivatives, see: Wang et al. (2012 ); Gao et al. (2009 ).

Experimental

Crystal data

[ZnI₂(C₁₇H₂₀N₂)₂]
M_r = 823.87
Monoclinic, P 2₁ /c
a = 13.724 (5) Å
b = 9.861 (8) Å
c = 27.742 (3) Å
β = 112.693 (12)°
V = 3464 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.52 mm⁻¹
T = 293 K
0.31 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.509, T_max = 0.607
23970 measured reflections
6097 independent reflections
3568 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.197
S = 1.04
6097 reflections
374 parameters
305 restraints
H-atom parameters constrained
Δρ_max = 1.44 e Å⁻³
Δρ_min = −0.95 e Å⁻³

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813001736/lr2093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001736/lr2093Isup2.hkl

checkCIF report

Comment top

In recent years, pyridine based materials have attracted considerable interests because of their significant applications in the areas of nonlinear optical (NLO), such as two-photon excited fluorescence (TPEF) microscopy, optical limiting. In addition, zinc complexes are particularly attractive and most studied for their biocompatibility (Wang et al., 2012; Gao et al., 2009). Herewith we present the structure of (I) which molecular structure is showed in Fig.1. The Zn^II is coordinated by the N atoms of two pyridine rings belonging to diferent ligands and two iodine atoms in a distorted tetrahedral geometry the Zn^II and with the coordinated pyridine moities oriented in an almost perpendicular fashion with a dihedral angle of 83.7 (5)°.

Related literature top

For the crystal structures of Zn complexes with related pyridine derivatives, see: Wang et al. (2012); Gao et al. (2009).

Experimental top

Fresh zinc iodide (0.32 g, 1 mmol) and the ligand (0.50 g, 2 mmol) were vigorously stirred in 15 ml of methanol until the solid phase had been completely dissolved, and then, the mixture was refluxed for 2 h. The reaction mixture was cooled to room temperature and filtered into a large test tube. Red brown needle crystals were obtained at room temperature after a week. Yield: 0.71 g (86%).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. : The molecular structure of the title molecule(I) showing 30% probability displacement ellipsoids.

Bis(4-{2-[4-(diethylamino)phenyl]ethenyl}pyridine-κN)diiodididozinc top

Crystal data top

[ZnI₂(C₁₇H₂₀N₂)₂]	F(000) = 1632
M_r = 823.87	D_x = 1.580 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3863 reflections
a = 13.724 (5) Å	θ = 2.2–19.1°
b = 9.861 (8) Å	µ = 2.52 mm⁻¹
c = 27.742 (3) Å	T = 293 K
β = 112.693 (12)°	Block, red
V = 3464 (3) Å³	0.31 × 0.23 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	6097 independent reflections
Radiation source: fine-focus sealed tube	3568 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
phi and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −16→16
T_min = 0.509, T_max = 0.607	k = −11→11
23970 measured reflections	l = −32→32

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0883P)² + 10.7456P] where P = (F_o² + 2F_c²)/3
6097 reflections	(Δ/σ)_max = 0.017
374 parameters	Δρ_max = 1.44 e Å⁻³
305 restraints	Δρ_min = −0.95 e Å⁻³

Crystal data top

[ZnI₂(C₁₇H₂₀N₂)₂]	V = 3464 (3) Å³
M_r = 823.87	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.724 (5) Å	µ = 2.52 mm⁻¹
b = 9.861 (8) Å	T = 293 K
c = 27.742 (3) Å	0.31 × 0.23 × 0.22 mm
β = 112.693 (12)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6097 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3568 reflections with I > 2σ(I)
T_min = 0.509, T_max = 0.607	R_int = 0.049
23970 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	305 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0883P)² + 10.7456P] where P = (F_o² + 2F_c²)/3
6097 reflections	Δρ_max = 1.44 e Å⁻³
374 parameters	Δρ_min = −0.95 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
I1	−0.08626 (6)	0.88056 (8)	0.28023 (3)	0.0904 (3)
I2	−0.14470 (6)	0.74792 (8)	0.41847 (3)	0.0923 (3)
Zn2	−0.07433 (8)	0.69644 (10)	0.34668 (4)	0.0633 (3)
N1	−0.1561 (6)	0.5329 (8)	0.3044 (3)	0.0682 (19)
N2	0.0736 (6)	0.6182 (7)	0.3834 (3)	0.0634 (19)
N3	0.7603 (9)	0.0057 (13)	0.5880 (5)	0.128 (3)
N4	−0.6764 (8)	−0.2949 (11)	0.1114 (5)	0.109 (3)
C1	−0.2622 (9)	0.5358 (13)	0.2838 (4)	0.092 (2)
H1	−0.2971	0.6131	0.2879	0.110*
C2	−0.1121 (10)	0.4205 (11)	0.2965 (4)	0.087 (2)
H2	−0.0387	0.4174	0.3099	0.104*
C3	−0.3218 (10)	0.4242 (13)	0.2560 (4)	0.097 (2)
H3	−0.3952	0.4289	0.2415	0.117*
C4	−0.1640 (10)	0.3098 (12)	0.2709 (4)	0.095 (2)
H4	−0.1260	0.2351	0.2673	0.114*
C5	−0.2702 (11)	0.3058 (12)	0.2504 (5)	0.098 (2)
C6	−0.3144 (9)	0.1787 (12)	0.2286 (4)	0.106 (2)
H6	−0.2692	0.1044	0.2358	0.128*
C7	−0.4166 (8)	0.1580 (12)	0.1984 (4)	0.099 (2)
H7	−0.4585	0.2355	0.1901	0.119*
C8	−0.4705 (9)	0.0341 (11)	0.1772 (5)	0.092 (2)
C9	−0.4359 (9)	−0.1008 (12)	0.1869 (5)	0.095 (2)
H9	−0.3662	−0.1185	0.2087	0.114*
C10	−0.5727 (9)	0.0500 (12)	0.1444 (5)	0.093 (2)
H10	−0.5982	0.1381	0.1367	0.111*
C11	−0.6412 (9)	−0.0537 (11)	0.1217 (5)	0.089 (2)
H11	−0.7099	−0.0341	0.0990	0.106*
C12	−0.5036 (9)	−0.2085 (12)	0.1644 (5)	0.092 (2)
H12	−0.4778	−0.2967	0.1712	0.111*
C13	−0.6097 (8)	−0.1874 (12)	0.1319 (5)	0.086 (2)
C14	−0.7856 (11)	−0.2734 (15)	0.0712 (6)	0.133 (4)
H14A	−0.7844	−0.1988	0.0487	0.160*
H14B	−0.8076	−0.3542	0.0497	0.160*
C15	−0.8634 (12)	−0.2437 (17)	0.0942 (7)	0.155 (5)
H15A	−0.8537	−0.3053	0.1225	0.233*
H15B	−0.9334	−0.2541	0.0680	0.233*
H15C	−0.8540	−0.1523	0.1071	0.233*
C16	−0.6404 (10)	−0.4364 (14)	0.1182 (5)	0.116 (3)
H16A	−0.5705	−0.4418	0.1173	0.140*
H16B	−0.6879	−0.4911	0.0898	0.140*
C17	−0.6373 (11)	−0.4898 (15)	0.1688 (5)	0.129 (4)
H17A	−0.5780	−0.4516	0.1969	0.194*
H17B	−0.6307	−0.5868	0.1693	0.194*
H17C	−0.7013	−0.4655	0.1730	0.194*
C18	0.0945 (8)	0.5466 (10)	0.4271 (4)	0.075 (2)
H18	0.0434	0.5395	0.4413	0.090*
C19	0.1497 (7)	0.6285 (10)	0.3646 (4)	0.075 (2)
H19	0.1373	0.6817	0.3351	0.090*
C20	0.2454 (7)	0.5636 (10)	0.3872 (4)	0.0739 (18)
H20	0.2948	0.5703	0.3719	0.089*
C21	0.1918 (8)	0.4819 (10)	0.4519 (4)	0.0741 (18)
H21	0.2043	0.4334	0.4825	0.089*
C22	0.2689 (7)	0.4886 (10)	0.4323 (4)	0.0712 (16)
C23	0.3707 (8)	0.4164 (10)	0.4555 (4)	0.0734 (18)
H23	0.4181	0.4263	0.4392	0.088*
C24	0.3997 (8)	0.3399 (10)	0.4970 (4)	0.0740 (18)
H24	0.3551	0.3402	0.5151	0.089*
C25	0.4923 (8)	0.2545 (11)	0.5185 (4)	0.0773 (17)
C26	0.5615 (9)	0.2317 (11)	0.4953 (4)	0.0835 (18)
H26	0.5499	0.2723	0.4633	0.100*
C27	0.5140 (8)	0.1901 (12)	0.5656 (4)	0.0846 (19)
H27	0.4676	0.2027	0.5823	0.101*
C28	0.6486 (8)	0.1497 (12)	0.5181 (4)	0.0881 (19)
H28	0.6944	0.1384	0.5010	0.106*
C29	0.5997 (8)	0.1090 (12)	0.5889 (4)	0.0896 (19)
H29	0.6108	0.0700	0.6211	0.108*
C30	0.6713 (9)	0.0831 (13)	0.5653 (5)	0.0906 (19)
C33	0.7943 (11)	−0.0354 (15)	0.6460 (6)	0.131 (3)
H33A	0.8699	−0.0503	0.6624	0.157*
H33B	0.7740	0.0327	0.6656	0.157*
C34	0.7347 (12)	−0.1634 (16)	0.6417 (7)	0.152 (5)
H34A	0.6606	−0.1465	0.6235	0.229*
H34B	0.7474	−0.1974	0.6760	0.229*
H34C	0.7576	−0.2292	0.6228	0.229*
C31	0.8072 (11)	−0.0722 (15)	0.5527 (6)	0.142 (3)
H31A	0.8343	−0.1626	0.5640	0.171*
H31B	0.7651	−0.0681	0.5155	0.171*
C32	0.8949 (11)	0.0225 (17)	0.5633 (7)	0.158 (4)
H32A	0.8684	0.1079	0.5469	0.238*
H32B	0.9440	−0.0136	0.5497	0.238*
H32C	0.9300	0.0353	0.6004	0.238*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0763 (5)	0.0786 (5)	0.0931 (6)	−0.0070 (4)	0.0071 (4)	0.0243 (4)
I2	0.0928 (6)	0.0935 (6)	0.0923 (6)	0.0125 (4)	0.0375 (4)	−0.0147 (4)
Zn2	0.0576 (6)	0.0539 (6)	0.0683 (7)	−0.0019 (5)	0.0132 (5)	−0.0030 (5)
N1	0.078 (4)	0.063 (4)	0.064 (4)	−0.015 (3)	0.028 (3)	−0.006 (3)
N2	0.064 (5)	0.051 (4)	0.068 (5)	0.000 (3)	0.017 (4)	0.004 (4)
N3	0.105 (5)	0.148 (6)	0.129 (5)	0.035 (4)	0.043 (4)	0.051 (5)
N4	0.090 (5)	0.093 (5)	0.141 (7)	−0.036 (5)	0.039 (5)	−0.038 (6)
C1	0.096 (5)	0.100 (5)	0.079 (5)	−0.029 (4)	0.032 (4)	−0.005 (4)
C2	0.103 (4)	0.078 (4)	0.078 (4)	−0.017 (3)	0.033 (4)	−0.010 (4)
C3	0.102 (4)	0.105 (4)	0.081 (4)	−0.035 (4)	0.031 (4)	−0.004 (4)
C4	0.116 (4)	0.086 (4)	0.079 (4)	−0.027 (3)	0.035 (4)	−0.012 (4)
C5	0.116 (4)	0.098 (4)	0.080 (4)	−0.038 (3)	0.037 (3)	−0.008 (3)
C6	0.116 (4)	0.108 (4)	0.092 (4)	−0.038 (4)	0.036 (4)	−0.013 (4)
C7	0.105 (4)	0.104 (4)	0.094 (4)	−0.035 (4)	0.044 (4)	−0.017 (4)
C8	0.091 (4)	0.092 (3)	0.098 (4)	−0.028 (3)	0.041 (3)	−0.018 (4)
C9	0.079 (4)	0.097 (4)	0.105 (5)	−0.024 (3)	0.032 (4)	−0.021 (4)
C10	0.092 (4)	0.082 (4)	0.104 (5)	−0.021 (3)	0.039 (4)	−0.019 (4)
C11	0.083 (4)	0.078 (4)	0.103 (5)	−0.015 (3)	0.034 (4)	−0.020 (4)
C12	0.075 (4)	0.088 (4)	0.109 (5)	−0.017 (3)	0.029 (4)	−0.021 (4)
C13	0.075 (4)	0.079 (4)	0.102 (5)	−0.017 (4)	0.032 (4)	−0.024 (4)
C14	0.112 (7)	0.117 (7)	0.166 (9)	−0.033 (6)	0.048 (6)	−0.035 (7)
C15	0.141 (9)	0.151 (10)	0.179 (11)	−0.027 (8)	0.068 (7)	−0.037 (9)
C16	0.105 (6)	0.110 (6)	0.131 (7)	−0.035 (5)	0.042 (6)	−0.040 (6)
C17	0.126 (8)	0.130 (9)	0.131 (8)	−0.034 (7)	0.048 (8)	−0.041 (7)
C18	0.070 (4)	0.073 (5)	0.081 (5)	0.008 (4)	0.029 (4)	0.013 (4)
C19	0.064 (4)	0.081 (5)	0.077 (5)	0.006 (4)	0.023 (4)	0.017 (4)
C20	0.062 (4)	0.080 (4)	0.079 (4)	0.005 (3)	0.027 (3)	0.013 (3)
C21	0.071 (3)	0.073 (4)	0.076 (4)	0.009 (3)	0.027 (3)	0.015 (3)
C22	0.064 (3)	0.071 (3)	0.076 (3)	0.005 (3)	0.023 (3)	0.010 (3)
C23	0.067 (3)	0.074 (4)	0.075 (4)	0.006 (3)	0.023 (3)	0.009 (3)
C24	0.069 (3)	0.078 (4)	0.073 (4)	0.008 (3)	0.025 (3)	0.009 (3)
C25	0.073 (3)	0.086 (4)	0.075 (3)	0.015 (3)	0.031 (3)	0.016 (3)
C26	0.082 (4)	0.097 (4)	0.076 (4)	0.022 (3)	0.036 (3)	0.023 (3)
C27	0.079 (4)	0.102 (4)	0.079 (4)	0.021 (3)	0.039 (3)	0.022 (3)
C28	0.082 (4)	0.109 (5)	0.082 (4)	0.026 (3)	0.042 (3)	0.029 (4)
C29	0.085 (4)	0.110 (5)	0.082 (4)	0.026 (3)	0.041 (3)	0.030 (4)
C30	0.085 (4)	0.112 (4)	0.086 (4)	0.029 (3)	0.044 (3)	0.033 (3)
C33	0.108 (6)	0.146 (7)	0.134 (5)	0.029 (5)	0.040 (5)	0.045 (6)
C34	0.132 (9)	0.147 (9)	0.154 (9)	0.015 (7)	0.029 (8)	0.027 (9)
C31	0.120 (6)	0.158 (7)	0.136 (6)	0.032 (5)	0.034 (5)	0.039 (6)
C32	0.129 (7)	0.164 (8)	0.149 (7)	0.021 (5)	0.017 (6)	0.042 (6)

Geometric parameters (Å, º) top

I1—Zn2	2.5473 (17)	C15—H15C	0.9600
I2—Zn2	2.5770 (14)	C16—C17	1.486 (9)
Zn2—N2	2.039 (7)	C16—H16A	0.9700
Zn2—N1	2.054 (8)	C16—H16B	0.9700
N1—C2	1.321 (13)	C17—H17A	0.9600
N1—C1	1.344 (13)	C17—H17B	0.9600
N2—C18	1.335 (12)	C17—H17C	0.9600
N2—C19	1.340 (12)	C18—C21	1.397 (13)
N3—C30	1.371 (14)	C18—H18	0.9300
N3—C33	1.546 (17)	C19—C20	1.376 (13)
N3—C31	1.564 (9)	C19—H19	0.9300
N4—C13	1.373 (13)	C20—C22	1.381 (13)
N4—C16	1.468 (16)	C20—H20	0.9300
N4—C14	1.499 (17)	C21—C22	1.366 (13)
C1—C3	1.410 (15)	C21—H21	0.9300
C1—H1	0.9300	C22—C23	1.477 (13)
C2—C4	1.347 (14)	C23—C24	1.304 (13)
C2—H2	0.9300	C23—H23	0.9300
C3—C5	1.405 (17)	C24—C25	1.448 (13)
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.345 (17)	C25—C26	1.355 (14)
C4—H4	0.9300	C25—C27	1.378 (14)
C5—C6	1.422 (9)	C26—C28	1.378 (14)
C6—C7	1.344 (8)	C26—H26	0.9300
C6—H6	0.9300	C27—C29	1.362 (14)
C7—C8	1.431 (9)	C27—H27	0.9300
C7—H7	0.9300	C28—C30	1.389 (14)
C8—C10	1.354 (15)	C28—H28	0.9300
C8—C9	1.404 (16)	C29—C30	1.398 (14)
C9—C12	1.390 (14)	C29—H29	0.9300
C9—H9	0.9300	C33—C34	1.484 (9)
C10—C11	1.368 (14)	C33—H33A	0.9700
C10—H10	0.9300	C33—H33B	0.9700
C11—C13	1.382 (15)	C34—H34A	0.9600
C11—H11	0.9300	C34—H34B	0.9600
C12—C13	1.402 (15)	C34—H34C	0.9600
C12—H12	0.9300	C31—C32	1.461 (9)
C14—C15	1.469 (9)	C31—H31A	0.9702
C14—H14A	0.9700	C31—H31B	0.9698
C14—H14B	0.9700	C32—H32A	0.9600
C15—H15A	0.9600	C32—H32B	0.9600
C15—H15B	0.9600	C32—H32C	0.9600

N2—Zn2—N1	102.0 (3)	N4—C16—H16B	109.6
N2—Zn2—I1	113.9 (2)	C17—C16—H16B	109.6
N1—Zn2—I1	106.1 (2)	H16A—C16—H16B	108.2
N2—Zn2—I2	106.6 (2)	C16—C17—H17A	109.5
N1—Zn2—I2	108.1 (2)	C16—C17—H17B	109.5
I1—Zn2—I2	118.71 (6)	H17A—C17—H17B	109.5
C2—N1—C1	115.9 (9)	C16—C17—H17C	109.5
C2—N1—Zn2	124.7 (7)	H17A—C17—H17C	109.5
C1—N1—Zn2	119.4 (8)	H17B—C17—H17C	109.5
C18—N2—C19	117.8 (8)	N2—C18—C21	121.3 (9)
C18—N2—Zn2	118.6 (7)	N2—C18—H18	119.3
C19—N2—Zn2	123.5 (6)	C21—C18—H18	119.3
C30—N3—C33	118.8 (11)	N2—C19—C20	122.6 (9)
C30—N3—C31	119.6 (11)	N2—C19—H19	118.7
C33—N3—C31	119.4 (11)	C20—C19—H19	118.7
C13—N4—C16	122.9 (11)	C19—C20—C22	120.6 (9)
C13—N4—C14	121.0 (11)	C19—C20—H20	119.7
C16—N4—C14	114.9 (10)	C22—C20—H20	119.7
N1—C1—C3	121.4 (12)	C22—C21—C18	121.4 (9)
N1—C1—H1	119.3	C22—C21—H21	119.3
C3—C1—H1	119.3	C18—C21—H21	119.3
N1—C2—C4	125.9 (12)	C21—C22—C20	116.2 (9)
N1—C2—H2	117.1	C21—C22—C23	123.4 (9)
C4—C2—H2	117.1	C20—C22—C23	120.3 (9)
C5—C3—C1	119.9 (12)	C24—C23—C22	125.4 (10)
C5—C3—H3	120.1	C24—C23—H23	117.3
C1—C3—H3	120.1	C22—C23—H23	117.3
C5—C4—C2	120.8 (13)	C23—C24—C25	128.3 (10)
C5—C4—H4	119.6	C23—C24—H24	115.8
C2—C4—H4	119.6	C25—C24—H24	115.8
C4—C5—C3	116.1 (10)	C26—C25—C27	116.0 (9)
C4—C5—C6	114.8 (12)	C26—C25—C24	124.5 (10)
C3—C5—C6	129.0 (12)	C27—C25—C24	119.5 (9)
C7—C6—C5	124.7 (12)	C25—C26—C28	121.5 (10)
C7—C6—H6	117.6	C25—C26—H26	119.2
C5—C6—H6	117.6	C28—C26—H26	119.2
C6—C7—C8	129.4 (12)	C29—C27—C25	123.5 (10)
C6—C7—H7	115.3	C29—C27—H27	118.3
C8—C7—H7	115.3	C25—C27—H27	118.3
C10—C8—C9	115.1 (10)	C26—C28—C30	123.3 (10)
C10—C8—C7	114.5 (11)	C26—C28—H28	118.3
C9—C8—C7	130.3 (12)	C30—C28—H28	118.3
C12—C9—C8	121.4 (11)	C27—C29—C30	121.3 (10)
C12—C9—H9	119.3	C27—C29—H29	119.4
C8—C9—H9	119.3	C30—C29—H29	119.4
C8—C10—C11	124.9 (12)	N3—C30—C28	122.3 (10)
C8—C10—H10	117.5	N3—C30—C29	123.3 (10)
C11—C10—H10	117.5	C28—C30—C29	114.3 (10)
C10—C11—C13	120.9 (11)	C34—C33—N3	101.7 (13)
C10—C11—H11	119.5	C34—C33—H33A	111.4
C13—C11—H11	119.5	N3—C33—H33A	111.4
C9—C12—C13	121.6 (12)	C34—C33—H33B	111.4
C9—C12—H12	119.2	N3—C33—H33B	111.4
C13—C12—H12	119.2	H33A—C33—H33B	109.3
N4—C13—C11	123.1 (11)	C33—C34—H34A	109.5
N4—C13—C12	120.9 (11)	C33—C34—H34B	109.5
C11—C13—C12	116.0 (10)	H34A—C34—H34B	109.5
C15—C14—N4	113.0 (14)	C33—C34—H34C	109.5
C15—C14—H14A	109.0	H34A—C34—H34C	109.5
N4—C14—H14A	109.0	H34B—C34—H34C	109.5
C15—C14—H14B	109.0	C32—C31—N3	93.8 (12)
N4—C14—H14B	109.0	C32—C31—H31A	109.8
H14A—C14—H14B	107.8	N3—C31—H31A	116.6
C14—C15—H15A	109.5	C32—C31—H31B	107.1
C14—C15—H15B	109.5	N3—C31—H31B	115.2
H15A—C15—H15B	109.5	H31A—C31—H31B	112.3
C14—C15—H15C	109.5	C31—C32—H32A	109.5
H15A—C15—H15C	109.5	C31—C32—H32B	109.4
H15B—C15—H15C	109.5	H32A—C32—H32B	109.5
N4—C16—C17	110.1 (12)	C31—C32—H32C	109.5
N4—C16—H16A	109.6	H32A—C32—H32C	109.5
C17—C16—H16A	109.6	H32B—C32—H32C	109.5

N2—Zn2—N1—C2	−12.9 (9)	C9—C12—C13—N4	−177.8 (12)
I1—Zn2—N1—C2	106.6 (8)	C9—C12—C13—C11	2.8 (18)
I2—Zn2—N1—C2	−125.0 (8)	C13—N4—C14—C15	−86.0 (16)
N2—Zn2—N1—C1	165.5 (7)	C16—N4—C14—C15	106.3 (14)
I1—Zn2—N1—C1	−75.0 (7)	C13—N4—C16—C17	84.5 (15)
I2—Zn2—N1—C1	53.3 (8)	C14—N4—C16—C17	−108.1 (13)
N1—Zn2—N2—C18	−82.1 (7)	C19—N2—C18—C21	−1.3 (14)
I1—Zn2—N2—C18	164.0 (6)	Zn2—N2—C18—C21	175.2 (7)
I2—Zn2—N2—C18	31.1 (7)	C18—N2—C19—C20	3.0 (14)
N1—Zn2—N2—C19	94.1 (8)	Zn2—N2—C19—C20	−173.3 (8)
I1—Zn2—N2—C19	−19.8 (8)	N2—C19—C20—C22	−2.9 (16)
I2—Zn2—N2—C19	−152.6 (7)	N2—C18—C21—C22	−0.5 (16)
C2—N1—C1—C3	0.7 (15)	C18—C21—C22—C20	0.7 (15)
Zn2—N1—C1—C3	−177.8 (8)	C18—C21—C22—C23	−176.7 (9)
C1—N1—C2—C4	−1.4 (16)	C19—C20—C22—C21	0.9 (15)
Zn2—N1—C2—C4	177.0 (9)	C19—C20—C22—C23	178.4 (10)
N1—C1—C3—C5	1.2 (17)	C21—C22—C23—C24	−0.6 (17)
N1—C2—C4—C5	0.0 (19)	C20—C22—C23—C24	−178.0 (11)
C2—C4—C5—C3	2.0 (18)	C22—C23—C24—C25	172.4 (10)
C2—C4—C5—C6	−174.6 (11)	C23—C24—C25—C26	−5.9 (19)
C1—C3—C5—C4	−2.6 (17)	C23—C24—C25—C27	174.3 (11)
C1—C3—C5—C6	173.5 (11)	C27—C25—C26—C28	−0.6 (18)
C4—C5—C6—C7	−167.9 (12)	C24—C25—C26—C28	179.6 (11)
C3—C5—C6—C7	16 (2)	C26—C25—C27—C29	0.8 (19)
C5—C6—C7—C8	−175.7 (12)	C24—C25—C27—C29	−179.4 (11)
C6—C7—C8—C10	−174.5 (13)	C25—C26—C28—C30	1 (2)
C6—C7—C8—C9	9 (2)	C25—C27—C29—C30	−1 (2)
C10—C8—C9—C12	−0.8 (18)	C33—N3—C30—C28	165.0 (13)
C7—C8—C9—C12	175.8 (12)	C31—N3—C30—C28	−32 (2)
C9—C8—C10—C11	0.8 (19)	C33—N3—C30—C29	−11 (2)
C7—C8—C10—C11	−176.4 (11)	C31—N3—C30—C29	152.4 (13)
C8—C10—C11—C13	1.1 (19)	C26—C28—C30—N3	−177.8 (13)
C8—C9—C12—C13	−1.0 (19)	C26—C28—C30—C29	−2 (2)
C16—N4—C13—C11	174.0 (12)	C27—C29—C30—N3	177.9 (13)
C14—N4—C13—C11	7.3 (18)	C27—C29—C30—C28	1.8 (19)
C16—N4—C13—C12	−5.3 (18)	C30—N3—C33—C34	88.2 (16)
C14—N4—C13—C12	−172.0 (12)	C31—N3—C33—C34	−75.0 (16)
C10—C11—C13—N4	177.8 (12)	C30—N3—C31—C32	104.9 (14)
C10—C11—C13—C12	−2.9 (17)	C33—N3—C31—C32	−92.0 (14)

Experimental details

Crystal data
Chemical formula	[ZnI₂(C₁₇H₂₀N₂)₂]
M_r	823.87
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.724 (5), 9.861 (8), 27.742 (3)
β (°)	112.693 (12)
V (Å³)	3464 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.52
Crystal size (mm)	0.31 × 0.23 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.509, 0.607
No. of measured, independent and observed [I > 2σ(I)] reflections	23970, 6097, 3568
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.197, 1.04
No. of reflections	6097
No. of parameters	374
No. of restraints	305
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0883P)² + 10.7456P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.44, −0.95

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 21071001 and 51142011).

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gao, Y., Wu, J., Li, Y., Sun, P., Zhou, H., Yang, J., Zhang, S., Jin, B. & Tian, Y. (2009). J. Am. Chem. Soc. 131, 5208–5213. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, X. C., Tian, X. H., Zhang, Q., Sun, P. P., Wu, J., Zhou, H., Jin, B., Yang, J. & Zhang, S. (2012). Chem. Mater. 24, 954–961. Web of Science CSD CrossRef CAS Google Scholar