metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Chemistry and Chemical Engineering, Institute of Materials Chemistry, Binzhou University, Binzhou 256603, People's Republic of China, and bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
*Correspondence e-mail: honglizhang1968@yahoo.cn

(Received 29 January 2008; accepted 18 February 2008; online 27 February 2008)

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[Makowska-Grzyska, M. M., Szajna, E., Shipley, C., Arif, A. M., Mitchell, M. H., Halfen, J. A. & Berreau, L. M. (2003). Inorg. Chem. 42, 7472-7488.]); Sun et al. (2003[Sun, H.-L., Gao, S., Ma, B.-Q. & Su, G. (2003). Inorg. Chem. 42, 5399-5404.]); Martin et al. (2001[Martin, S., Barandika, M. G., Larramendi, J. I. R., Cortes, R., Font-Bardia, M., Lezama, L., Serna, Z. E., Solans, X. & Rojo, T. (2001). Inorg. Chem. 40, 3687-3692.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C2N3)(C18H18N4)]ClO4

  • Mr = 521.23

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.702, Tmax = 0.803

  • 12346 measured reflections

  • 4800 independent reflections

  • 3352 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 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

Table 1
Selected geometric parameters (Å, °)

N1—Zn1 2.053 (2)
N2—Zn1 2.048 (2)
N3—Zn1 2.059 (2)
N4—Zn1 2.215 (2)
N5—Zn1 2.021 (3)
N5—Zn1—N2 101.94 (10)
N5—Zn1—N1 100.96 (11)
N2—Zn1—N1 118.19 (9)
N5—Zn1—N3 100.98 (10)
N2—Zn1—N3 117.58 (9)
N1—Zn1—N3 112.99 (9)
N5—Zn1—N4 179.41 (10)
N2—Zn1—N4 78.60 (9)
N1—Zn1—N4 78.95 (9)
N3—Zn1—N4 78.55 (9)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯O4i 0.93 2.53 3.272 (4) 138
C7—H7B⋯O2ii 0.97 2.59 3.455 (4) 148
C10—H10⋯O1iii 0.93 2.58 3.511 (5) 179
C13—H13A⋯N6iv 0.97 2.61 3.457 (5) 146
C16—H16⋯N7′v 0.93 2.48 3.412 (18) 178
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) -x, -y+1, -z; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) -x+1, -y+2, -z; (v) x, y-1, z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. View of complex (I), showing the the atom numbering scheme with thermal ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure showing weak hydrogen bonds as dashed lines.
(Dicyanamido)[tris(2-pyridylmethyl)amine]zinc(II) perchlorate top
Crystal data top
[Zn(C2N3)(C18H18N4)]ClO4F(000) = 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 = 2.3–22.0°
b = 10.8578 (18) ŵ = 1.27 mm1
c = 14.653 (2) ÅT = 298 K
β = 91.590 (3)°Block, colorless
V = 2215.5 (6) Å30.30 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
4800 independent reflections
Radiation source: fine-focus sealed tube3352 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ϕ and ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1517
Tmin = 0.702, Tmax = 0.803k = 1312
12346 measured reflectionsl = 1816
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.053P)2]
where P = (Fo2 + 2Fc2)/3
4800 reflections(Δ/σ)max = 0.001
308 parametersΔρmax = 0.36 e Å3
1 restraintΔρmin = 0.25 e Å3
Crystal data top
[Zn(C2N3)(C18H18N4)]ClO4V = 2215.5 (6) Å3
Mr = 521.23Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.931 (2) ŵ = 1.27 mm1
b = 10.8578 (18) ÅT = 298 K
c = 14.653 (2) Å0.30 × 0.20 × 0.18 mm
β = 91.590 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
4800 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3352 reflections with I > 2σ(I)
Tmin = 0.702, Tmax = 0.803Rint = 0.035
12346 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.106H-atom parameters constrained
S = 0.99Δρmax = 0.36 e Å3
4800 reflectionsΔρmin = 0.25 e Å3
308 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.

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*/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*
H7B0.07020.82170.03010.076*
C80.1729 (2)0.9441 (3)0.0664 (2)0.0519 (7)
C90.1372 (3)0.9713 (3)0.1530 (2)0.0691 (9)
H90.07690.94310.17220.083*
C100.1913 (4)1.0397 (4)0.2098 (2)0.0812 (11)
H100.16841.05900.26830.097*
C110.2798 (3)1.0797 (3)0.1801 (2)0.0786 (11)
H110.31771.12670.21800.094*
C120.3118 (3)1.0497 (3)0.0937 (2)0.0617 (8)
H120.37191.07740.07360.074*
C130.2121 (2)0.6901 (3)0.0215 (2)0.0628 (9)
H13A0.21590.70160.04390.075*
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) top
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, º) top
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—N21.0 (5)N7'—C19—N5—Zn171 (7)
C2—C1—C5—N20.6 (4)N5—C19—N7—C20138.7 (19)
C2—C1—C5—C6175.2 (3)N7'—C19—N7—C2061 (3)
N2—C5—C6—N427.9 (3)N6—C20—N7—C19134 (2)
C1—C5—C6—N4156.1 (3)N7'—C20—N7—C1965 (3)
N4—C7—C8—N133.0 (4)N6—C20—N7'—C19141 (3)
N4—C7—C8—C9150.0 (3)N7—C20—N7'—C1962 (2)
N1—C8—C9—C100.7 (5)N5—C19—N7'—C20142 (3)
C7—C8—C9—C10176.1 (3)N7—C19—N7'—C2066 (3)
C8—C9—C10—C110.1 (6)C19—N5—Zn1—N260.5 (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—N330.8 (4)C5—N2—Zn1—N5167.30 (19)
N4—C13—C14—C15151.5 (3)C4—N2—Zn1—N512.5 (2)
N3—C14—C15—C160.8 (5)C5—N2—Zn1—N183.2 (2)
C13—C14—C15—C16176.8 (4)C4—N2—Zn1—N197.0 (2)
C14—C15—C16—C170.1 (7)C5—N2—Zn1—N358.0 (2)
C15—C16—C17—C181.3 (7)C4—N2—Zn1—N3121.8 (2)
C16—C17—C18—N31.6 (6)C5—N2—Zn1—N412.47 (18)
C11—C12—N1—C80.8 (5)C4—N2—Zn1—N4167.7 (2)
C11—C12—N1—Zn1175.7 (2)C12—N1—Zn1—N514.7 (3)
C9—C8—N1—C121.0 (4)C8—N1—Zn1—N5168.7 (2)
C7—C8—N1—C12176.0 (3)C12—N1—Zn1—N2124.8 (2)
C9—C8—N1—Zn1175.8 (2)C8—N1—Zn1—N258.7 (2)
C7—C8—N1—Zn17.2 (3)C12—N1—Zn1—N392.3 (2)
C1—C5—N2—C40.2 (4)C8—N1—Zn1—N384.2 (2)
C6—C5—N2—C4175.8 (2)C12—N1—Zn1—N4164.7 (3)
C1—C5—N2—Zn1180.0 (2)C8—N1—Zn1—N411.9 (2)
C6—C5—N2—Zn14.0 (3)C14—N3—Zn1—N5170.4 (2)
C3—C4—N2—C50.6 (4)C18—N3—Zn1—N515.8 (3)
C3—C4—N2—Zn1179.2 (2)C14—N3—Zn1—N279.8 (2)
C15—C14—N3—C180.6 (4)C18—N3—Zn1—N294.1 (3)
C13—C14—N3—C18177.2 (3)C14—N3—Zn1—N163.4 (2)
C15—C14—N3—Zn1173.6 (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—N4164.6 (3)
C17—C18—N3—Zn1174.4 (3)C6—N4—Zn1—N225.66 (18)
C5—C6—N4—C779.4 (3)C7—N4—Zn1—N294.61 (19)
C5—C6—N4—C13150.8 (2)C13—N4—Zn1—N2145.91 (19)
C5—C6—N4—Zn134.7 (3)C6—N4—Zn1—N1147.68 (19)
C8—C7—N4—C6153.5 (3)C7—N4—Zn1—N127.42 (18)
C8—C7—N4—C1376.7 (3)C13—N4—Zn1—N192.06 (19)
C8—C7—N4—Zn138.6 (3)C6—N4—Zn1—N395.86 (18)
C14—C13—N4—C680.8 (3)C7—N4—Zn1—N3143.9 (2)
C14—C13—N4—C7148.9 (2)C13—N4—Zn1—N324.39 (18)
Hydrogen-bond geometry (Å, º) top
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···N7v0.932.483.412 (18)178
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+1, z; (iii) x, y+3/2, z1/2; (iv) x+1, y+2, z; (v) x, y1, z.

Experimental details

Crystal data
Chemical formula[Zn(C2N3)(C18H18N4)]ClO4
Mr521.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)13.931 (2), 10.8578 (18), 14.653 (2)
β (°) 91.590 (3)
V3)2215.5 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.27
Crystal size (mm)0.30 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.702, 0.803
No. of measured, independent and
observed [I > 2σ(I)] reflections
12346, 4800, 3352
Rint0.035
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.106, 0.99
No. of reflections4800
No. of parameters308
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.25

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
N1—Zn12.053 (2)N4—Zn12.215 (2)
N2—Zn12.048 (2)N5—Zn12.021 (3)
N3—Zn12.059 (2)
N5—Zn1—N2101.94 (10)N1—Zn1—N3112.99 (9)
N5—Zn1—N1100.96 (11)N5—Zn1—N4179.41 (10)
N2—Zn1—N1118.19 (9)N2—Zn1—N478.60 (9)
N5—Zn1—N3100.98 (10)N1—Zn1—N478.95 (9)
N2—Zn1—N3117.58 (9)N3—Zn1—N478.55 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.932.533.272 (4)137.5
C7—H7B···O2ii0.972.593.455 (4)148.1
C10—H10···O1iii0.932.583.511 (5)178.7
C13—H13A···N6iv0.972.613.457 (5)146.0
C16—H16···N7'v0.932.483.412 (18)178.1
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+1, z; (iii) x, y+3/2, z1/2; (iv) x+1, y+2, z; (v) x, y1, z.
 

Acknowledgements

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

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMakowska-Grzyska, M. M., Szajna, E., Shipley, C., Arif, A. M., Mitchell, M. H., Halfen, J. A. & Berreau, L. M. (2003). Inorg. Chem. 42, 7472–7488.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationMartin, S., Barandika, M. G., Larramendi, J. I. R., Cortes, R., Font-Bardia, M., Lezama, L., Serna, Z. E., Solans, X. & Rojo, T. (2001). Inorg. Chem. 40, 3687–3692.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, H.-L., Gao, S., Ma, B.-Q. & Su, G. (2003). Inorg. Chem. 42, 5399–5404.  Web of Science CSD CrossRef PubMed 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds