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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): m495.
Published online 2008 February 27. doi:  10.1107/S1600536808004741
PMCID: PMC2960752

(Dicyanamido)[tris­(2-pyridylmeth­yl)amine]zinc(II) perchlorate

Abstract

In the title complex, [Zn(C2N3)(C18H18N4)]ClO4, the ZnII ion has a slightly distorted trigonal–bipyramidal ZnN5 coordination geometry. The crystal structure is stabilized by weak inter­molecular C—H(...)O and C—H(...)N hydrogen bonds. In addition, there are relatively close contacts between the O atoms of the perchlorate anion and symmetry-related pyridine rings [O(...)Cg = 3.179 (3) and 3.236 (3) Å, where Cg is the centroid of a pyridine ring], and between the terminal N atom of the dicyanamide ligand and pyridine rings [N(...)Cg = 3.381 (4)–3.761 (3) Å]. The central N atom of the dicyanamide ligand is disordered over two sites in an approximately 0.6:0.4 ratio.

Related literature

For related literature, see: Makowska-Grzyska et al. (2003 [triangle]); Sun et al. (2003 [triangle]); Martin et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m495-scheme1.jpg

Experimental

Crystal data

  • [Zn(C2N3)(C18H18N4)]ClO4
  • M r = 521.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m495-efi1.jpg
  • a = 13.931 (2) Å
  • b = 10.8578 (18) Å
  • c = 14.653 (2) Å
  • β = 91.590 (3)°
  • V = 2215.5 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.27 mm−1
  • T = 298 (2) K
  • 0.30 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.702, T max = 0.803
  • 12346 measured reflections
  • 4800 independent reflections
  • 3352 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.106
  • S = 0.99
  • 4800 reflections
  • 308 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004741/lh2594sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004741/lh2594Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Natural Science Foundation of Shandong Province of China (grant No. Y2007B26).

supplementary crystallographic information

Comment

Tris[(2-pyridyl)methylene)amine is a very common terminal ligand and many complexes containing this ligand have been reported, including some Zn(II) complexes with perchlorate anions (e.g. Makowska-Grzyska et al., 2003) such as in the title compound. The dicyanamide anion can play a role as bridging ligand to form multi-nuclear complexes (e.g. Sun et al., 2003; Martin et al., 2001). As part of our work we wanted to prepare a coordination polymer with dicyanamide group acting as a bridging ligand and tris[(2-pyridyl)methylene)amine as terminal ligand, but instead we obtained the title mononuclear five-coordinated Zn(II) complex (I) and its crystal structure is reported herein. At this time there appears to be no other published examples of crystal structures of complexes of the two above mentioned ligands both coordinated to a transition metal.

The title complex is shown in Fig. 1. The ZnII ion is in a slightly distorted trigonal-bipyramidal coordination geometry. In the crystal structure, there are weak hydrogen bonds formed between complex cations and perchlorate anions, and between symmetry related complex cations (Fig. 2). In addition there also exists interactions between Cl—O bonds and π-rings systems and between C—N bonds and π-ring systems, and the relevant distances (Å) are as follows: Cl1—O2···Cg1i = 3.236 (3), Cl1—O2···Cg1iperp = 3.120; Cl1—O4···Cg2i = 3.179 (3), Cl1—O4···Cg2iperp = 3.111; C20—N6···Cg2ii = 3.381 (4), C20—N6···Cg2iiperp = 3.360; C20—N6···Cg1iii = 3.453 (4), C20—N6···Cg1iiiperp = 3.156; C20—N6···Cg3iii = 3.761 (3), C20—N6···Cg3iiiperp = 3.365; (Cg1, Cg2 and Cg3 are the centroids of N2/C1—C5 ring, N1/C8—C12 ring and N3/C14—C18 ring, respectively; A—B···Cgjperp is the perpendicular distance from B atom to ring j; symmetry codes: (i) x,-1 + y,z; (ii) 1 - x,2 - y,-z; (iii) 1 - x,1/2 + y,1/2 - z).

Experimental

A 10 ml me thanol solution of tris[(2-pyridyl)methylene]amine (0.2103 g, 0.72 mmol) was added into 20 ml H2O solution containing Zn(ClO4)6H2O (0.2621 g, 0.70 mmol) and sodium dicyanamide (0.0645 g, 0.72 mmol), and the mixture was stirred for a few minutes. Colorless single crystals were obtained after the filtrate had been allowed to stand at room temperature for 10 d.

Refinement

The central N atom of the dicyanamide ligand is disorded over two sites in a 0.40 (7): 60 (7) ratio (sum constrained to unity). H atoms were placed in calculated positions (C—H = 0.97 Å for methylene group and C—H = 0.93 Å for other H atoms) and refined as riding with Uiso = 1.2 Ueq(C).

Figures

Fig. 1.
View of complex (I), showing the the atom numbering scheme with thermal ellipsoids drawn at the 30% probability level.
Fig. 2.
Part of the crystal structure showing weak hydrogen bonds as dashed lines.

Crystal data

[Zn(C2N3)(C18H18N4)]ClO4F000 = 1064
Mr = 521.23Dx = 1.563 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2616 reflections
a = 13.931 (2) Åθ = 2.3–22.0º
b = 10.8578 (18) ŵ = 1.27 mm1
c = 14.653 (2) ÅT = 298 (2) K
β = 91.590 (3)ºBlock, colorless
V = 2215.5 (6) Å30.30 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer4800 independent reflections
Radiation source: fine-focus sealed tube3352 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
T = 298(2) Kθmax = 27.0º
[var phi] and ω scansθmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −15→17
Tmin = 0.702, Tmax = 0.803k = −13→12
12346 measured reflectionsl = −18→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.106  w = 1/[σ2(Fo2) + (0.053P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
4800 reflectionsΔρmax = 0.36 e Å3
308 parametersΔρmin = −0.25 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/UeqOcc. (<1)
C10.0860 (2)0.9139 (3)0.2853 (2)0.0612 (9)
H10.03370.86270.29470.073*
C20.1044 (3)1.0115 (4)0.3423 (2)0.0697 (10)
H20.06481.02720.39100.084*
C30.1813 (3)1.0854 (3)0.3270 (2)0.0674 (9)
H30.19521.15170.36540.081*
C40.2375 (2)1.0607 (3)0.2547 (2)0.0545 (8)
H40.28941.11220.24390.065*
C50.14649 (19)0.8927 (3)0.21361 (19)0.0461 (7)
C60.1355 (2)0.7823 (3)0.1528 (2)0.0562 (8)
H6A0.16690.71220.18160.067*
H6B0.06780.76290.14450.067*
C70.1151 (2)0.8761 (3)0.0017 (2)0.0629 (9)
H7A0.07840.93450.03670.076*
H7B0.07020.8217−0.03010.076*
C80.1729 (2)0.9441 (3)−0.0664 (2)0.0519 (7)
C90.1372 (3)0.9713 (3)−0.1530 (2)0.0691 (9)
H90.07690.9431−0.17220.083*
C100.1913 (4)1.0397 (4)−0.2098 (2)0.0812 (11)
H100.16841.0590−0.26830.097*
C110.2798 (3)1.0797 (3)−0.1801 (2)0.0786 (11)
H110.31771.1267−0.21800.094*
C120.3118 (3)1.0497 (3)−0.0937 (2)0.0617 (8)
H120.37191.0774−0.07360.074*
C130.2121 (2)0.6901 (3)0.0215 (2)0.0628 (9)
H13A0.21590.7016−0.04390.075*
H13B0.16760.62330.03240.075*
C140.3093 (2)0.6574 (3)0.0606 (2)0.0554 (8)
C150.3413 (4)0.5360 (3)0.0654 (3)0.0844 (12)
H150.30100.47180.04690.101*
C160.4314 (4)0.5126 (4)0.0972 (3)0.1041 (15)
H160.45350.43180.10080.125*
C170.4900 (3)0.6072 (4)0.1240 (3)0.0947 (14)
H170.55260.59220.14480.114*
C180.4545 (2)0.7252 (3)0.1195 (2)0.0681 (9)
H180.49360.78990.13920.082*
C190.4657 (2)1.1134 (3)0.1232 (2)0.0594 (8)
C200.5964 (3)1.2341 (3)0.1587 (2)0.0670 (9)
Cl10.13251 (5)0.26686 (7)0.06625 (5)0.0551 (2)
N10.25963 (17)0.9822 (2)−0.03743 (15)0.0474 (6)
N20.22133 (15)0.9657 (2)0.19860 (14)0.0425 (5)
N30.36571 (17)0.7501 (2)0.08790 (16)0.0500 (6)
N40.17686 (15)0.8038 (2)0.06381 (15)0.0461 (6)
N50.42095 (18)1.0295 (3)0.11270 (19)0.0626 (7)
N60.6718 (3)1.2592 (3)0.1805 (2)0.1036 (12)
N70.5015 (14)1.214 (2)0.157 (3)0.066 (7)0.40 (7)
N7'0.5148 (16)1.2179 (15)0.116 (3)0.100 (5)0.60 (7)
O10.1054 (2)0.3925 (2)0.06831 (17)0.0854 (8)
O20.08216 (17)0.2017 (2)0.13439 (16)0.0821 (7)
O30.23268 (17)0.2569 (3)0.0827 (2)0.0980 (8)
O40.1080 (2)0.2177 (2)−0.02084 (16)0.0905 (8)
Zn10.30405 (2)0.92245 (3)0.08979 (2)0.04138 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0467 (17)0.086 (3)0.0509 (19)0.0100 (16)0.0088 (14)0.0197 (18)
C20.081 (3)0.086 (3)0.0423 (19)0.024 (2)0.0134 (17)0.0048 (18)
C30.089 (3)0.067 (2)0.0456 (19)0.0119 (19)0.0039 (18)−0.0042 (16)
C40.0615 (19)0.056 (2)0.0459 (18)0.0023 (14)−0.0017 (15)0.0004 (14)
C50.0401 (15)0.0575 (18)0.0404 (16)0.0022 (13)−0.0029 (12)0.0081 (13)
C60.0447 (17)0.068 (2)0.0564 (19)−0.0167 (15)0.0066 (14)0.0053 (15)
C70.0424 (17)0.090 (2)0.056 (2)−0.0105 (16)−0.0095 (15)0.0053 (18)
C80.0528 (18)0.0588 (19)0.0437 (17)0.0085 (14)−0.0041 (14)0.0003 (14)
C90.083 (2)0.076 (2)0.048 (2)0.0142 (19)−0.0125 (18)−0.0030 (18)
C100.123 (4)0.075 (3)0.045 (2)0.025 (2)−0.006 (2)0.0083 (18)
C110.120 (3)0.062 (2)0.055 (2)0.005 (2)0.020 (2)0.0158 (17)
C120.074 (2)0.0515 (19)0.061 (2)−0.0001 (16)0.0158 (17)0.0026 (15)
C130.074 (2)0.056 (2)0.059 (2)−0.0263 (17)0.0047 (17)−0.0095 (15)
C140.075 (2)0.0442 (17)0.0481 (17)−0.0047 (15)0.0153 (15)−0.0035 (14)
C150.119 (4)0.046 (2)0.089 (3)0.001 (2)0.030 (3)0.0011 (19)
C160.138 (4)0.067 (3)0.108 (4)0.043 (3)0.033 (3)0.018 (3)
C170.090 (3)0.100 (4)0.095 (3)0.048 (3)0.007 (2)0.012 (3)
C180.061 (2)0.073 (2)0.070 (2)0.0125 (17)0.0050 (18)0.0036 (18)
C190.0489 (18)0.0545 (18)0.074 (2)−0.0062 (12)−0.0102 (16)0.0012 (17)
C200.071 (2)0.058 (2)0.072 (2)−0.0248 (18)−0.0010 (19)−0.0053 (17)
Cl10.0535 (4)0.0568 (5)0.0552 (5)−0.0035 (3)0.0042 (4)0.0010 (4)
N10.0524 (14)0.0476 (14)0.0424 (13)0.0022 (11)0.0063 (11)0.0037 (11)
N20.0419 (13)0.0463 (13)0.0391 (13)0.0032 (10)−0.0033 (10)0.0028 (10)
N30.0524 (15)0.0494 (14)0.0484 (15)0.0025 (11)0.0044 (11)0.0023 (11)
N40.0411 (13)0.0553 (15)0.0421 (13)−0.0109 (11)0.0025 (10)0.0002 (11)
N50.0485 (15)0.0609 (16)0.0784 (19)−0.0141 (11)0.0000 (13)−0.0056 (14)
N60.090 (2)0.118 (3)0.103 (3)−0.050 (2)0.010 (2)−0.037 (2)
N70.060 (6)0.040 (8)0.096 (15)−0.005 (5)−0.014 (8)0.007 (6)
N7'0.089 (7)0.082 (6)0.128 (15)−0.040 (5)−0.042 (8)0.052 (7)
O10.107 (2)0.0644 (16)0.0849 (19)0.0212 (14)0.0130 (15)0.0035 (13)
O20.0737 (16)0.1009 (19)0.0720 (16)−0.0049 (13)0.0058 (13)0.0369 (14)
O30.0550 (15)0.0947 (19)0.144 (2)−0.0051 (13)0.0035 (15)0.0138 (17)
O40.110 (2)0.098 (2)0.0639 (16)−0.0235 (16)0.0170 (14)−0.0221 (14)
Zn10.03599 (18)0.0427 (2)0.0454 (2)−0.00542 (13)0.00088 (13)−0.00063 (14)

Geometric parameters (Å, °)

C1—C21.368 (5)C13—C141.498 (4)
C1—C51.384 (4)C13—H13A0.9700
C1—H10.9300C13—H13B0.9700
C2—C31.362 (5)C14—N31.332 (4)
C2—H20.9300C14—C151.392 (5)
C3—C41.362 (4)C15—C161.352 (6)
C3—H30.9300C15—H150.9300
C4—N21.334 (3)C16—C171.363 (6)
C4—H40.9300C16—H160.9300
C5—N21.333 (3)C17—C181.374 (5)
C5—C61.499 (4)C17—H170.9300
C6—N41.458 (3)C18—N31.336 (4)
C6—H6A0.9700C18—H180.9300
C6—H6B0.9700C19—N51.112 (4)
C7—N41.463 (4)C19—N71.294 (17)
C7—C81.495 (4)C19—N7'1.331 (14)
C7—H7A0.9700C20—N61.122 (4)
C7—H7B0.9700C20—N7'1.298 (16)
C8—N11.335 (4)C20—N71.34 (2)
C8—C91.382 (4)Cl1—O31.414 (2)
C9—C101.359 (5)Cl1—O41.416 (2)
C9—H90.9300Cl1—O11.416 (2)
C10—C111.367 (6)Cl1—O21.424 (2)
C10—H100.9300N1—Zn12.053 (2)
C11—C121.369 (5)N2—Zn12.048 (2)
C11—H110.9300N3—Zn12.059 (2)
C12—N11.334 (4)N4—Zn12.215 (2)
C12—H120.9300N5—Zn12.021 (3)
C13—N41.472 (4)
C2—C1—C5119.0 (3)C16—C15—C14119.3 (4)
C2—C1—H1120.5C16—C15—H15120.4
C5—C1—H1120.5C14—C15—H15120.4
C3—C2—C1119.4 (3)C15—C16—C17120.0 (4)
C3—C2—H2120.3C15—C16—H16120.0
C1—C2—H2120.3C17—C16—H16120.0
C2—C3—C4118.9 (3)C16—C17—C18118.5 (4)
C2—C3—H3120.5C16—C17—H17120.7
C4—C3—H3120.5C18—C17—H17120.7
N2—C4—C3122.7 (3)N3—C18—C17122.3 (4)
N2—C4—H4118.6N3—C18—H18118.9
C3—C4—H4118.6C17—C18—H18118.9
N2—C5—C1121.4 (3)N5—C19—N7162.3 (19)
N2—C5—C6116.4 (2)N5—C19—N7'166.9 (17)
C1—C5—C6122.0 (3)N6—C20—N7'166.3 (18)
N4—C6—C5111.5 (2)N6—C20—N7163.6 (17)
N4—C6—H6A109.3O3—Cl1—O4109.71 (18)
C5—C6—H6A109.3O3—Cl1—O1109.44 (17)
N4—C6—H6B109.3O4—Cl1—O1108.92 (16)
C5—C6—H6B109.3O3—Cl1—O2110.20 (16)
H6A—C6—H6B108.0O4—Cl1—O2109.48 (16)
N4—C7—C8111.2 (2)O1—Cl1—O2109.07 (16)
N4—C7—H7A109.4C12—N1—C8118.5 (3)
C8—C7—H7A109.4C12—N1—Zn1125.4 (2)
N4—C7—H7B109.4C8—N1—Zn1115.97 (19)
C8—C7—H7B109.4C5—N2—C4118.6 (3)
H7A—C7—H7B108.0C5—N2—Zn1116.86 (19)
N1—C8—C9121.7 (3)C4—N2—Zn1124.6 (2)
N1—C8—C7116.1 (2)C14—N3—C18118.9 (3)
C9—C8—C7122.1 (3)C14—N3—Zn1116.6 (2)
C10—C9—C8119.2 (4)C18—N3—Zn1124.2 (2)
C10—C9—H9120.4C6—N4—C7113.7 (2)
C8—C9—H9120.4C6—N4—C13112.7 (2)
C9—C10—C11119.3 (3)C7—N4—C13112.7 (2)
C9—C10—H10120.4C6—N4—Zn1105.89 (16)
C11—C10—H10120.4C7—N4—Zn1104.41 (17)
C10—C11—C12119.1 (3)C13—N4—Zn1106.58 (17)
C10—C11—H11120.4C19—N5—Zn1160.0 (3)
C12—C11—H11120.4C19—N7—C20120.9 (14)
N1—C12—C11122.2 (3)C20—N7'—C19121.4 (13)
N1—C12—H12118.9N5—Zn1—N2101.94 (10)
C11—C12—H12118.9N5—Zn1—N1100.96 (11)
N4—C13—C14110.3 (2)N2—Zn1—N1118.19 (9)
N4—C13—H13A109.6N5—Zn1—N3100.98 (10)
C14—C13—H13A109.6N2—Zn1—N3117.58 (9)
N4—C13—H13B109.6N1—Zn1—N3112.99 (9)
C14—C13—H13B109.6N5—Zn1—N4179.41 (10)
H13A—C13—H13B108.1N2—Zn1—N478.60 (9)
N3—C14—C15121.0 (3)N1—Zn1—N478.95 (9)
N3—C14—C13117.1 (3)N3—Zn1—N478.55 (9)
C15—C14—C13121.9 (3)
C5—C1—C2—C30.2 (5)C14—C13—N4—Zn134.9 (3)
C1—C2—C3—C40.6 (5)N7—C19—N5—Zn163 (5)
C2—C3—C4—N2−1.0 (5)N7'—C19—N5—Zn1−71 (7)
C2—C1—C5—N2−0.6 (4)N5—C19—N7—C20138.7 (19)
C2—C1—C5—C6175.2 (3)N7'—C19—N7—C20−61 (3)
N2—C5—C6—N4−27.9 (3)N6—C20—N7—C19−134 (2)
C1—C5—C6—N4156.1 (3)N7'—C20—N7—C1965 (3)
N4—C7—C8—N1−33.0 (4)N6—C20—N7'—C19141 (3)
N4—C7—C8—C9150.0 (3)N7—C20—N7'—C19−62 (2)
N1—C8—C9—C10−0.7 (5)N5—C19—N7'—C20−142 (3)
C7—C8—C9—C10176.1 (3)N7—C19—N7'—C2066 (3)
C8—C9—C10—C110.1 (6)C19—N5—Zn1—N2−60.5 (8)
C9—C10—C11—C120.1 (6)C19—N5—Zn1—N161.7 (8)
C10—C11—C12—N10.2 (5)C19—N5—Zn1—N3178.0 (8)
N4—C13—C14—N3−30.8 (4)C5—N2—Zn1—N5−167.30 (19)
N4—C13—C14—C15151.5 (3)C4—N2—Zn1—N512.5 (2)
N3—C14—C15—C16−0.8 (5)C5—N2—Zn1—N183.2 (2)
C13—C14—C15—C16176.8 (4)C4—N2—Zn1—N1−97.0 (2)
C14—C15—C16—C17−0.1 (7)C5—N2—Zn1—N3−58.0 (2)
C15—C16—C17—C181.3 (7)C4—N2—Zn1—N3121.8 (2)
C16—C17—C18—N3−1.6 (6)C5—N2—Zn1—N412.47 (18)
C11—C12—N1—C8−0.8 (5)C4—N2—Zn1—N4−167.7 (2)
C11—C12—N1—Zn1175.7 (2)C12—N1—Zn1—N514.7 (3)
C9—C8—N1—C121.0 (4)C8—N1—Zn1—N5−168.7 (2)
C7—C8—N1—C12−176.0 (3)C12—N1—Zn1—N2124.8 (2)
C9—C8—N1—Zn1−175.8 (2)C8—N1—Zn1—N2−58.7 (2)
C7—C8—N1—Zn17.2 (3)C12—N1—Zn1—N3−92.3 (2)
C1—C5—N2—C40.2 (4)C8—N1—Zn1—N384.2 (2)
C6—C5—N2—C4−175.8 (2)C12—N1—Zn1—N4−164.7 (3)
C1—C5—N2—Zn1−180.0 (2)C8—N1—Zn1—N411.9 (2)
C6—C5—N2—Zn14.0 (3)C14—N3—Zn1—N5−170.4 (2)
C3—C4—N2—C50.6 (4)C18—N3—Zn1—N515.8 (3)
C3—C4—N2—Zn1−179.2 (2)C14—N3—Zn1—N279.8 (2)
C15—C14—N3—C180.6 (4)C18—N3—Zn1—N2−94.1 (3)
C13—C14—N3—C18−177.2 (3)C14—N3—Zn1—N1−63.4 (2)
C15—C14—N3—Zn1−173.6 (2)C18—N3—Zn1—N1122.8 (2)
C13—C14—N3—Zn18.6 (3)C14—N3—Zn1—N49.3 (2)
C17—C18—N3—C140.7 (5)C18—N3—Zn1—N4−164.6 (3)
C17—C18—N3—Zn1174.4 (3)C6—N4—Zn1—N2−25.66 (18)
C5—C6—N4—C7−79.4 (3)C7—N4—Zn1—N294.61 (19)
C5—C6—N4—C13150.8 (2)C13—N4—Zn1—N2−145.91 (19)
C5—C6—N4—Zn134.7 (3)C6—N4—Zn1—N1−147.68 (19)
C8—C7—N4—C6153.5 (3)C7—N4—Zn1—N1−27.42 (18)
C8—C7—N4—C13−76.7 (3)C13—N4—Zn1—N192.06 (19)
C8—C7—N4—Zn138.6 (3)C6—N4—Zn1—N395.86 (18)
C14—C13—N4—C6−80.8 (3)C7—N4—Zn1—N3−143.9 (2)
C14—C13—N4—C7148.9 (2)C13—N4—Zn1—N3−24.39 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.932.533.272 (4)138
C7—H7B···O2ii0.972.593.455 (4)148
C10—H10···O1iii0.932.583.511 (5)179
C13—H13A···N6iv0.972.613.457 (5)146
C16—H16···N7'v0.932.483.412 (18)178

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+1, −z; (iii) x, −y+3/2, z−1/2; (iv) −x+1, −y+2, −z; (v) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2594).

References

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  • Sun, H.-L., Gao, S., Ma, B.-Q. & Su, G. (2003). Inorg. Chem.42, 5399–5404. [PubMed]

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