supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

lr2093 scheme

Acta Cryst. (2013). E69, m135    [ doi:10.1107/S1600536813001736 ]

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

C.-Y. Nie and Y.-P. Tian

Abstract top

In the title compound, [ZnI2(C17H20N2)2], the ZnII 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)°.

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 ZnII is coordinated by the N atoms of two pyridine rings belonging to diferent ligands and two iodine atoms in a distorted tetrahedral geometry the ZnII 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%).

Refinement top

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq.

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
[Figure 1] 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
Mr = 823.87Dx = 1.580 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 3863 reflections
a = 13.724 (5) Åθ = 2.2–19.1°
b = 9.861 (8) ŵ = 2.52 mm−1
c = 27.742 (3) ÅT = 293 K
β = 112.693 (12)°Block, red
V = 3464 (3) Å30.31 × 0.23 × 0.22 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		6097 independent reflections
Radiation source: fine-focus sealed tube3568 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
phi and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −16→16
Tmin = 0.509, Tmax = 0.607k = −11→11
23970 measured reflectionsl = −32→32
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0883P)2 + 10.7456P]
where P = (Fo2 + 2Fc2)/3
6097 reflections(Δ/σ)max = 0.017
374 parametersΔρmax = 1.44 e Å−3
305 restraintsΔρmin = −0.95 e Å−3
Crystal data top
[ZnI2(C17H20N2)2]V = 3464 (3) Å3
Mr = 823.87Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.724 (5) ŵ = 2.52 mm−1
b = 9.861 (8) ÅT = 293 K
c = 27.742 (3) Å0.31 × 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)
Tmin = 0.509, Tmax = 0.607Rint = 0.049
23970 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.063 w = 1/[σ2(Fo2) + (0.0883P)2 + 10.7456P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.197Δρmax = 1.44 e Å−3
S = 1.04Δρmin = −0.95 e Å−3
6097 reflectionsAbsolute structure: ?
374 parametersFlack parameter: ?
305 restraintsRogers parameter: ?
H-atom parameters constrained
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
xyzUiso*/Ueq
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)
N20.0736 (6)0.6182 (7)0.3834 (3)0.0634 (19)
N30.7603 (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)
H1−0.29710.61310.28790.110*
C2−0.1121 (10)0.4205 (11)0.2965 (4)0.087 (2)
H2−0.03870.41740.30990.104*
C3−0.3218 (10)0.4242 (13)0.2560 (4)0.097 (2)
H3−0.39520.42890.24150.117*
C4−0.1640 (10)0.3098 (12)0.2709 (4)0.095 (2)
H4−0.12600.23510.26730.114*
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)
H6−0.26920.10440.23580.128*
C7−0.4166 (8)0.1580 (12)0.1984 (4)0.099 (2)
H7−0.45850.23550.19010.119*
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)
H9−0.3662−0.11850.20870.114*
C10−0.5727 (9)0.0500 (12)0.1444 (5)0.093 (2)
H10−0.59820.13810.13670.111*
C11−0.6412 (9)−0.0537 (11)0.1217 (5)0.089 (2)
H11−0.7099−0.03410.09900.106*
C12−0.5036 (9)−0.2085 (12)0.1644 (5)0.092 (2)
H12−0.4778−0.29670.17120.111*
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−0.7844−0.19880.04870.160*
H14B−0.8076−0.35420.04970.160*
C15−0.8634 (12)−0.2437 (17)0.0942 (7)0.155 (5)
H15A−0.8537−0.30530.12250.233*
H15B−0.9334−0.25410.06800.233*
H15C−0.8540−0.15230.10710.233*
C16−0.6404 (10)−0.4364 (14)0.1182 (5)0.116 (3)
H16A−0.5705−0.44180.11730.140*
H16B−0.6879−0.49110.08980.140*
C17−0.6373 (11)−0.4898 (15)0.1688 (5)0.129 (4)
H17A−0.5780−0.45160.19690.194*
H17B−0.6307−0.58680.16930.194*
H17C−0.7013−0.46550.17300.194*
C180.0945 (8)0.5466 (10)0.4271 (4)0.075 (2)
H180.04340.53950.44130.090*
C190.1497 (7)0.6285 (10)0.3646 (4)0.075 (2)
H190.13730.68170.33510.090*
C200.2454 (7)0.5636 (10)0.3872 (4)0.0739 (18)
H200.29480.57030.37190.089*
C210.1918 (8)0.4819 (10)0.4519 (4)0.0741 (18)
H210.20430.43340.48250.089*
C220.2689 (7)0.4886 (10)0.4323 (4)0.0712 (16)
C230.3707 (8)0.4164 (10)0.4555 (4)0.0734 (18)
H230.41810.42630.43920.088*
C240.3997 (8)0.3399 (10)0.4970 (4)0.0740 (18)
H240.35510.34020.51510.089*
C250.4923 (8)0.2545 (11)0.5185 (4)0.0773 (17)
C260.5615 (9)0.2317 (11)0.4953 (4)0.0835 (18)
H260.54990.27230.46330.100*
C270.5140 (8)0.1901 (12)0.5656 (4)0.0846 (19)
H270.46760.20270.58230.101*
C280.6486 (8)0.1497 (12)0.5181 (4)0.0881 (19)
H280.69440.13840.50100.106*
C290.5997 (8)0.1090 (12)0.5889 (4)0.0896 (19)
H290.61080.07000.62110.108*
C300.6713 (9)0.0831 (13)0.5653 (5)0.0906 (19)
C330.7943 (11)−0.0354 (15)0.6460 (6)0.131 (3)
H33A0.8699−0.05030.66240.157*
H33B0.77400.03270.66560.157*
C340.7347 (12)−0.1634 (16)0.6417 (7)0.152 (5)
H34A0.6606−0.14650.62350.229*
H34B0.7474−0.19740.67600.229*
H34C0.7576−0.22920.62280.229*
C310.8072 (11)−0.0722 (15)0.5527 (6)0.142 (3)
H31A0.8343−0.16260.56400.171*
H31B0.7651−0.06810.51550.171*
C320.8949 (11)0.0225 (17)0.5633 (7)0.158 (4)
H32A0.86840.10790.54690.238*
H32B0.9440−0.01360.54970.238*
H32C0.93000.03530.60040.238*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0763 (5)0.0786 (5)0.0931 (6)−0.0070 (4)0.0071 (4)0.0243 (4)
I20.0928 (6)0.0935 (6)0.0923 (6)0.0125 (4)0.0375 (4)−0.0147 (4)
Zn20.0576 (6)0.0539 (6)0.0683 (7)−0.0019 (5)0.0132 (5)−0.0030 (5)
N10.078 (4)0.063 (4)0.064 (4)−0.015 (3)0.028 (3)−0.006 (3)
N20.064 (5)0.051 (4)0.068 (5)0.000 (3)0.017 (4)0.004 (4)
N30.105 (5)0.148 (6)0.129 (5)0.035 (4)0.043 (4)0.051 (5)
N40.090 (5)0.093 (5)0.141 (7)−0.036 (5)0.039 (5)−0.038 (6)
C10.096 (5)0.100 (5)0.079 (5)−0.029 (4)0.032 (4)−0.005 (4)
C20.103 (4)0.078 (4)0.078 (4)−0.017 (3)0.033 (4)−0.010 (4)
C30.102 (4)0.105 (4)0.081 (4)−0.035 (4)0.031 (4)−0.004 (4)
C40.116 (4)0.086 (4)0.079 (4)−0.027 (3)0.035 (4)−0.012 (4)
C50.116 (4)0.098 (4)0.080 (4)−0.038 (3)0.037 (3)−0.008 (3)
C60.116 (4)0.108 (4)0.092 (4)−0.038 (4)0.036 (4)−0.013 (4)
C70.105 (4)0.104 (4)0.094 (4)−0.035 (4)0.044 (4)−0.017 (4)
C80.091 (4)0.092 (3)0.098 (4)−0.028 (3)0.041 (3)−0.018 (4)
C90.079 (4)0.097 (4)0.105 (5)−0.024 (3)0.032 (4)−0.021 (4)
C100.092 (4)0.082 (4)0.104 (5)−0.021 (3)0.039 (4)−0.019 (4)
C110.083 (4)0.078 (4)0.103 (5)−0.015 (3)0.034 (4)−0.020 (4)
C120.075 (4)0.088 (4)0.109 (5)−0.017 (3)0.029 (4)−0.021 (4)
C130.075 (4)0.079 (4)0.102 (5)−0.017 (4)0.032 (4)−0.024 (4)
C140.112 (7)0.117 (7)0.166 (9)−0.033 (6)0.048 (6)−0.035 (7)
C150.141 (9)0.151 (10)0.179 (11)−0.027 (8)0.068 (7)−0.037 (9)
C160.105 (6)0.110 (6)0.131 (7)−0.035 (5)0.042 (6)−0.040 (6)
C170.126 (8)0.130 (9)0.131 (8)−0.034 (7)0.048 (8)−0.041 (7)
C180.070 (4)0.073 (5)0.081 (5)0.008 (4)0.029 (4)0.013 (4)
C190.064 (4)0.081 (5)0.077 (5)0.006 (4)0.023 (4)0.017 (4)
C200.062 (4)0.080 (4)0.079 (4)0.005 (3)0.027 (3)0.013 (3)
C210.071 (3)0.073 (4)0.076 (4)0.009 (3)0.027 (3)0.015 (3)
C220.064 (3)0.071 (3)0.076 (3)0.005 (3)0.023 (3)0.010 (3)
C230.067 (3)0.074 (4)0.075 (4)0.006 (3)0.023 (3)0.009 (3)
C240.069 (3)0.078 (4)0.073 (4)0.008 (3)0.025 (3)0.009 (3)
C250.073 (3)0.086 (4)0.075 (3)0.015 (3)0.031 (3)0.016 (3)
C260.082 (4)0.097 (4)0.076 (4)0.022 (3)0.036 (3)0.023 (3)
C270.079 (4)0.102 (4)0.079 (4)0.021 (3)0.039 (3)0.022 (3)
C280.082 (4)0.109 (5)0.082 (4)0.026 (3)0.042 (3)0.029 (4)
C290.085 (4)0.110 (5)0.082 (4)0.026 (3)0.041 (3)0.030 (4)
C300.085 (4)0.112 (4)0.086 (4)0.029 (3)0.044 (3)0.033 (3)
C330.108 (6)0.146 (7)0.134 (5)0.029 (5)0.040 (5)0.045 (6)
C340.132 (9)0.147 (9)0.154 (9)0.015 (7)0.029 (8)0.027 (9)
C310.120 (6)0.158 (7)0.136 (6)0.032 (5)0.034 (5)0.039 (6)
C320.129 (7)0.164 (8)0.149 (7)0.021 (5)0.017 (6)0.042 (6)
Geometric parameters (Å, º) top
I1—Zn22.5473 (17)C15—H15C0.9600
I2—Zn22.5770 (14)C16—C171.486 (9)
Zn2—N22.039 (7)C16—H16A0.9700
Zn2—N12.054 (8)C16—H16B0.9700
N1—C21.321 (13)C17—H17A0.9600
N1—C11.344 (13)C17—H17B0.9600
N2—C181.335 (12)C17—H17C0.9600
N2—C191.340 (12)C18—C211.397 (13)
N3—C301.371 (14)C18—H180.9300
N3—C331.546 (17)C19—C201.376 (13)
N3—C311.564 (9)C19—H190.9300
N4—C131.373 (13)C20—C221.381 (13)
N4—C161.468 (16)C20—H200.9300
N4—C141.499 (17)C21—C221.366 (13)
C1—C31.410 (15)C21—H210.9300
C1—H10.9300C22—C231.477 (13)
C2—C41.347 (14)C23—C241.304 (13)
C2—H20.9300C23—H230.9300
C3—C51.405 (17)C24—C251.448 (13)
C3—H30.9300C24—H240.9300
C4—C51.345 (17)C25—C261.355 (14)
C4—H40.9300C25—C271.378 (14)
C5—C61.422 (9)C26—C281.378 (14)
C6—C71.344 (8)C26—H260.9300
C6—H60.9300C27—C291.362 (14)
C7—C81.431 (9)C27—H270.9300
C7—H70.9300C28—C301.389 (14)
C8—C101.354 (15)C28—H280.9300
C8—C91.404 (16)C29—C301.398 (14)
C9—C121.390 (14)C29—H290.9300
C9—H90.9300C33—C341.484 (9)
C10—C111.368 (14)C33—H33A0.9700
C10—H100.9300C33—H33B0.9700
C11—C131.382 (15)C34—H34A0.9600
C11—H110.9300C34—H34B0.9600
C12—C131.402 (15)C34—H34C0.9600
C12—H120.9300C31—C321.461 (9)
C14—C151.469 (9)C31—H31A0.9702
C14—H14A0.9700C31—H31B0.9698
C14—H14B0.9700C32—H32A0.9600
C15—H15A0.9600C32—H32B0.9600
C15—H15B0.9600C32—H32C0.9600
N2—Zn2—N1102.0 (3)N4—C16—H16B109.6
N2—Zn2—I1113.9 (2)C17—C16—H16B109.6
N1—Zn2—I1106.1 (2)H16A—C16—H16B108.2
N2—Zn2—I2106.6 (2)C16—C17—H17A109.5
N1—Zn2—I2108.1 (2)C16—C17—H17B109.5
I1—Zn2—I2118.71 (6)H17A—C17—H17B109.5
C2—N1—C1115.9 (9)C16—C17—H17C109.5
C2—N1—Zn2124.7 (7)H17A—C17—H17C109.5
C1—N1—Zn2119.4 (8)H17B—C17—H17C109.5
C18—N2—C19117.8 (8)N2—C18—C21121.3 (9)
C18—N2—Zn2118.6 (7)N2—C18—H18119.3
C19—N2—Zn2123.5 (6)C21—C18—H18119.3
C30—N3—C33118.8 (11)N2—C19—C20122.6 (9)
C30—N3—C31119.6 (11)N2—C19—H19118.7
C33—N3—C31119.4 (11)C20—C19—H19118.7
C13—N4—C16122.9 (11)C19—C20—C22120.6 (9)
C13—N4—C14121.0 (11)C19—C20—H20119.7
C16—N4—C14114.9 (10)C22—C20—H20119.7
N1—C1—C3121.4 (12)C22—C21—C18121.4 (9)
N1—C1—H1119.3C22—C21—H21119.3
C3—C1—H1119.3C18—C21—H21119.3
N1—C2—C4125.9 (12)C21—C22—C20116.2 (9)
N1—C2—H2117.1C21—C22—C23123.4 (9)
C4—C2—H2117.1C20—C22—C23120.3 (9)
C5—C3—C1119.9 (12)C24—C23—C22125.4 (10)
C5—C3—H3120.1C24—C23—H23117.3
C1—C3—H3120.1C22—C23—H23117.3
C5—C4—C2120.8 (13)C23—C24—C25128.3 (10)
C5—C4—H4119.6C23—C24—H24115.8
C2—C4—H4119.6C25—C24—H24115.8
C4—C5—C3116.1 (10)C26—C25—C27116.0 (9)
C4—C5—C6114.8 (12)C26—C25—C24124.5 (10)
C3—C5—C6129.0 (12)C27—C25—C24119.5 (9)
C7—C6—C5124.7 (12)C25—C26—C28121.5 (10)
C7—C6—H6117.6C25—C26—H26119.2
C5—C6—H6117.6C28—C26—H26119.2
C6—C7—C8129.4 (12)C29—C27—C25123.5 (10)
C6—C7—H7115.3C29—C27—H27118.3
C8—C7—H7115.3C25—C27—H27118.3
C10—C8—C9115.1 (10)C26—C28—C30123.3 (10)
C10—C8—C7114.5 (11)C26—C28—H28118.3
C9—C8—C7130.3 (12)C30—C28—H28118.3
C12—C9—C8121.4 (11)C27—C29—C30121.3 (10)
C12—C9—H9119.3C27—C29—H29119.4
C8—C9—H9119.3C30—C29—H29119.4
C8—C10—C11124.9 (12)N3—C30—C28122.3 (10)
C8—C10—H10117.5N3—C30—C29123.3 (10)
C11—C10—H10117.5C28—C30—C29114.3 (10)
C10—C11—C13120.9 (11)C34—C33—N3101.7 (13)
C10—C11—H11119.5C34—C33—H33A111.4
C13—C11—H11119.5N3—C33—H33A111.4
C9—C12—C13121.6 (12)C34—C33—H33B111.4
C9—C12—H12119.2N3—C33—H33B111.4
C13—C12—H12119.2H33A—C33—H33B109.3
N4—C13—C11123.1 (11)C33—C34—H34A109.5
N4—C13—C12120.9 (11)C33—C34—H34B109.5
C11—C13—C12116.0 (10)H34A—C34—H34B109.5
C15—C14—N4113.0 (14)C33—C34—H34C109.5
C15—C14—H14A109.0H34A—C34—H34C109.5
N4—C14—H14A109.0H34B—C34—H34C109.5
C15—C14—H14B109.0C32—C31—N393.8 (12)
N4—C14—H14B109.0C32—C31—H31A109.8
H14A—C14—H14B107.8N3—C31—H31A116.6
C14—C15—H15A109.5C32—C31—H31B107.1
C14—C15—H15B109.5N3—C31—H31B115.2
H15A—C15—H15B109.5H31A—C31—H31B112.3
C14—C15—H15C109.5C31—C32—H32A109.5
H15A—C15—H15C109.5C31—C32—H32B109.4
H15B—C15—H15C109.5H32A—C32—H32B109.5
N4—C16—C17110.1 (12)C31—C32—H32C109.5
N4—C16—H16A109.6H32A—C32—H32C109.5
C17—C16—H16A109.6H32B—C32—H32C109.5
N2—Zn2—N1—C2−12.9 (9)C9—C12—C13—N4−177.8 (12)
I1—Zn2—N1—C2106.6 (8)C9—C12—C13—C112.8 (18)
I2—Zn2—N1—C2−125.0 (8)C13—N4—C14—C15−86.0 (16)
N2—Zn2—N1—C1165.5 (7)C16—N4—C14—C15106.3 (14)
I1—Zn2—N1—C1−75.0 (7)C13—N4—C16—C1784.5 (15)
I2—Zn2—N1—C153.3 (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—C18164.0 (6)Zn2—N2—C18—C21175.2 (7)
I2—Zn2—N2—C1831.1 (7)C18—N2—C19—C203.0 (14)
N1—Zn2—N2—C1994.1 (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—C30.7 (15)C18—C21—C22—C200.7 (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—C210.9 (15)
Zn2—N1—C2—C4177.0 (9)C19—C20—C22—C23178.4 (10)
N1—C1—C3—C51.2 (17)C21—C22—C23—C24−0.6 (17)
N1—C2—C4—C50.0 (19)C20—C22—C23—C24−178.0 (11)
C2—C4—C5—C32.0 (18)C22—C23—C24—C25172.4 (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—C27174.3 (11)
C1—C3—C5—C6173.5 (11)C27—C25—C26—C28−0.6 (18)
C4—C5—C6—C7−167.9 (12)C24—C25—C26—C28179.6 (11)
C3—C5—C6—C716 (2)C26—C25—C27—C290.8 (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—C301 (2)
C6—C7—C8—C99 (2)C25—C27—C29—C30−1 (2)
C10—C8—C9—C12−0.8 (18)C33—N3—C30—C28165.0 (13)
C7—C8—C9—C12175.8 (12)C31—N3—C30—C28−32 (2)
C9—C8—C10—C110.8 (19)C33—N3—C30—C29−11 (2)
C7—C8—C10—C11−176.4 (11)C31—N3—C30—C29152.4 (13)
C8—C10—C11—C131.1 (19)C26—C28—C30—N3−177.8 (13)
C8—C9—C12—C13−1.0 (19)C26—C28—C30—C29−2 (2)
C16—N4—C13—C11174.0 (12)C27—C29—C30—N3177.9 (13)
C14—N4—C13—C117.3 (18)C27—C29—C30—C281.8 (19)
C16—N4—C13—C12−5.3 (18)C30—N3—C33—C3488.2 (16)
C14—N4—C13—C12−172.0 (12)C31—N3—C33—C34−75.0 (16)
C10—C11—C13—N4177.8 (12)C30—N3—C31—C32104.9 (14)
C10—C11—C13—C12−2.9 (17)C33—N3—C31—C32−92.0 (14)
Acknowledgements top

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

references
References top

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

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.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

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.