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

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COMMUNICATIONS
ISSN: 2056-9890

Perchloratobis[1-(1,10-phenanthrolin-2-yl)-2-pyridone]zinc(II) perchlorate

aSchool of Chemical & Environmental Engineering, Shandong University of Science and Technology, Qingdao 266510, People's Republic of China, and bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
*Correspondence e-mail: qinyunliu1972@163.com

(Received 22 June 2009; accepted 1 July 2009; online 8 July 2009)

In the title mononuclear complex, [Zn(ClO4)(C17H11N3O)2]ClO4, the ZnII ion is coordinated in a distorted octa­hedral geometry. The dihedral angles between the pyridine rings and the mean planes of the 1,10-phenanthroline ring system in each of the 1-(1,10-phenanthrolin-2-yl)-2-pyridone (PP) ligands is 24.51 (10)° for the tridendate PP ligand and 73.55 (6)° for the bidentate PP ligand. Within the mol­ecule there is a weak ππ inter­action between the pyridine ring of the bidentate ligand and the 1,10-phenanthroline ring system of the tridendate ligand with a centroid–centroid distance of 3.6383 (19) Å.

Related literature

For a related crystal structure and background information, see: Liu et al. (2008[Liu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58-m60.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(ClO4)(C17H11N3O)2]ClO4

  • Mr = 810.85

  • Monoclinic, P 21 /n

  • a = 12.998 (2) Å

  • b = 16.741 (3) Å

  • c = 14.680 (3) Å

  • β = 100.068 (2)°

  • V = 3145.2 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.03 mm−1

  • T = 298 K

  • 0.45 × 0.38 × 0.26 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 = 0.655, Tmax = 0.776

  • 16722 measured reflections

  • 6163 independent reflections

  • 5005 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.130

  • S = 1.08

  • 6163 reflections

  • 480 parameters

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −0.63 e Å−3

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

Metal complexes containing derivatives of 1,10-phenanthroline as ligands play a pivotal role in the area of modern coordination chemistry. One of the first metal complexes containing the 1-(1,10-phenanthrolin-2-yl)-2-pyridone (PP) ligand was published recently (Liu et al., 2008 and references cited within). Our interest in this area motivated us to synthesize the title complex, and here we report its crystal structure.

The asymmetric unit of the title compound (I) is shown in Fig. 1. The data of coordination bond lengths and associated angles (Table 1) indicate that the ZnII ion is in a distorted octahedral geometry. The dihedral angles between pyridine rings and the mean planes of the 1,10-phenanthroline ring system in each of the 1-(1,10-phenanthrolin-2-yl)-2-pyridone (PP) ligands is 24.51 (10)° for the tridendate PP ligand and 73.55 (6)° for the bidentate PP ligand. There is a weak ππ interaction with Cg1···Cg2 = 3.6376 (19)Å and Cg1···Cg2perp = 3.569 Å; α is 15.63° [Cg1 and Cg2 are the centroids of C23C24C27-C29/N4 ring and C13—C17/N5 ring, respectively; Cg1···Cg2iperp is the perpendicular distance from ring Cg1 to ring Cg2; α is the dihedral angle between the Cg1 ring plane and the Cg2 ring plane].

Related literature top

For a related crystal structure and background information, see: Liu et al. (2008).

Experimental top

Hydrated zinc perchlorate (0.2418 g, 0.65 mmol) and 1-(1,10-phenanthrolin-2-yl)-2-pyridone (0.1774 g, 0.65 mmol) were dissolved in 10 ml methanol, and the solution was stirred for a few minutes. Yellow single crystals were obtained after the filtrate had been allowed to stand at room temperature for one week.

Refinement top

All H atoms were placed in calculated positions, and refined as riding, with C—H = 0.93 Å and Uiso(H) = 1.2eq(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. The asymmetric unit of (I) showing the atom numbering scheme with thermal ellipsoids drawn at the 30% probability level.
Perchloratobis[1-(1,10-phenanthrolin-2-yl)-2-pyridone]zinc(II) perchlorate top
Crystal data top
[Zn(ClO4)(C17H11N3O)2]ClO4F(000) = 1648
Mr = 810.85Dx = 1.712 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6273 reflections
a = 12.998 (2) Åθ = 2.3–27.0°
b = 16.741 (3) ŵ = 1.03 mm1
c = 14.680 (3) ÅT = 298 K
β = 100.068 (2)°Block, yellow
V = 3145.2 (10) Å30.45 × 0.38 × 0.26 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
6163 independent reflections
Radiation source: fine-focus sealed tube5005 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1216
Tmin = 0.655, Tmax = 0.776k = 2019
16722 measured reflectionsl = 1718
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0839P)2 + 0.2024P]
where P = (Fo2 + 2Fc2)/3
6163 reflections(Δ/σ)max = 0.001
480 parametersΔρmax = 0.82 e Å3
0 restraintsΔρmin = 0.63 e Å3
Crystal data top
[Zn(ClO4)(C17H11N3O)2]ClO4V = 3145.2 (10) Å3
Mr = 810.85Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.998 (2) ŵ = 1.03 mm1
b = 16.741 (3) ÅT = 298 K
c = 14.680 (3) Å0.45 × 0.38 × 0.26 mm
β = 100.068 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
6163 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5005 reflections with I > 2σ(I)
Tmin = 0.655, Tmax = 0.776Rint = 0.028
16722 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.08Δρmax = 0.82 e Å3
6163 reflectionsΔρmin = 0.63 e Å3
480 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*/Ueq
C10.1039 (2)0.10171 (18)0.5679 (2)0.0474 (7)
H10.06810.06300.59550.057*
C20.1066 (3)0.09526 (19)0.4745 (2)0.0535 (8)
H20.07420.05240.44080.064*
C30.1568 (2)0.1520 (2)0.4320 (2)0.0505 (8)
H30.15730.14900.36880.061*
C40.2076 (2)0.21493 (17)0.48458 (19)0.0395 (6)
C50.20322 (19)0.21620 (15)0.57950 (18)0.0331 (6)
C60.25810 (19)0.27716 (15)0.63721 (18)0.0313 (5)
C70.3130 (2)0.33617 (16)0.5965 (2)0.0370 (6)
C80.2632 (2)0.27598 (19)0.4458 (2)0.0450 (7)
H80.26450.27590.38270.054*
C90.3140 (2)0.33375 (18)0.4999 (2)0.0439 (7)
H90.35050.37280.47350.053*
C100.3663 (2)0.39396 (16)0.6561 (2)0.0440 (7)
H100.40150.43510.63200.053*
C110.3670 (2)0.39036 (18)0.7479 (2)0.0481 (8)
H110.40240.42860.78730.058*
C120.3138 (2)0.32829 (16)0.7828 (2)0.0382 (6)
C130.2868 (3)0.3608 (2)1.0268 (2)0.0610 (9)
H130.25370.39431.06320.073*
C140.3496 (3)0.3029 (2)1.0683 (2)0.0624 (9)
H140.35890.29691.13220.075*
C150.4010 (3)0.25162 (19)1.0158 (2)0.0590 (9)
H150.44480.21171.04460.071*
C160.3864 (2)0.26046 (18)0.9239 (2)0.0498 (7)
H160.42050.22640.88880.060*
C170.2688 (3)0.37307 (19)0.9287 (2)0.0507 (8)
C180.3225 (2)0.04946 (19)0.7636 (2)0.0497 (8)
H180.32010.06050.70110.060*
C190.3877 (2)0.0110 (2)0.8049 (3)0.0617 (9)
H190.42800.04010.77020.074*
C200.3924 (3)0.02735 (19)0.8950 (3)0.0579 (9)
H200.43670.06750.92250.069*
C210.3313 (2)0.01527 (16)0.9483 (2)0.0447 (7)
C220.2667 (2)0.07564 (15)0.90174 (19)0.0349 (6)
C230.2012 (2)0.12133 (15)0.95101 (18)0.0330 (6)
C240.1966 (2)0.10129 (16)1.04237 (19)0.0381 (6)
C250.2612 (2)0.03954 (18)1.0871 (2)0.0484 (7)
H250.25780.02661.14810.058*
C260.3269 (2)0.00048 (18)1.0429 (2)0.0525 (8)
H260.37040.03921.07450.063*
C270.0828 (2)0.22394 (15)0.94907 (18)0.0334 (6)
C280.0674 (2)0.20372 (18)1.0379 (2)0.0433 (7)
H280.01770.23061.06480.052*
C290.1256 (2)0.14452 (17)1.0849 (2)0.0437 (7)
H290.11830.13271.14540.052*
C300.0805 (3)0.35800 (18)0.7785 (2)0.0520 (8)
H60.11050.36000.71620.062*
C310.0005 (3)0.35034 (18)0.9622 (2)0.0501 (8)
H310.02850.34941.02480.060*
C320.0680 (3)0.40880 (19)0.9300 (3)0.0584 (9)
H320.08580.44730.97010.070*
C330.1111 (3)0.41155 (19)0.8361 (3)0.0588 (9)
H330.16070.45010.81370.071*
C340.0037 (2)0.29806 (15)0.8084 (2)0.0378 (6)
Cl10.05475 (7)0.33552 (5)0.23847 (6)0.0555 (2)
Cl20.06238 (5)0.05947 (4)0.78950 (5)0.03671 (17)
N10.25867 (16)0.27400 (12)0.72957 (15)0.0331 (5)
N20.15024 (18)0.16100 (13)0.62039 (15)0.0359 (5)
N30.26358 (17)0.09182 (13)0.81097 (16)0.0371 (5)
N40.14672 (16)0.18319 (11)0.90497 (15)0.0306 (5)
N50.32214 (18)0.31891 (13)0.88079 (16)0.0398 (5)
N60.02718 (18)0.29118 (13)0.90430 (16)0.0378 (5)
O10.2131 (2)0.42378 (16)0.88607 (18)0.0763 (8)
O20.03168 (15)0.25565 (11)0.75179 (13)0.0405 (4)
O30.03026 (16)0.07488 (12)0.75009 (15)0.0481 (5)
O40.03149 (17)0.03559 (13)0.88350 (15)0.0530 (5)
O50.12309 (19)0.12974 (14)0.78672 (19)0.0675 (7)
O60.1177 (2)0.00388 (17)0.73801 (17)0.0728 (7)
O70.0442 (3)0.3557 (2)0.3300 (2)0.1018 (10)
O80.0400 (3)0.3197 (3)0.1845 (3)0.147 (2)
O90.0971 (5)0.3960 (3)0.1999 (4)0.204 (3)
O100.1218 (5)0.2717 (3)0.2398 (3)0.208 (3)
Zn10.15585 (2)0.180720 (18)0.76169 (2)0.03378 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0607 (19)0.0447 (17)0.0382 (17)0.0144 (14)0.0122 (14)0.0046 (13)
C20.069 (2)0.0489 (18)0.0416 (18)0.0119 (15)0.0075 (15)0.0141 (14)
C30.0567 (19)0.064 (2)0.0315 (16)0.0010 (16)0.0106 (14)0.0058 (14)
C40.0419 (15)0.0451 (15)0.0323 (15)0.0039 (12)0.0089 (12)0.0034 (12)
C50.0349 (14)0.0356 (14)0.0302 (14)0.0023 (11)0.0093 (11)0.0015 (11)
C60.0317 (13)0.0307 (13)0.0333 (14)0.0025 (10)0.0102 (10)0.0032 (10)
C70.0364 (14)0.0340 (13)0.0433 (16)0.0027 (11)0.0140 (12)0.0085 (12)
C80.0476 (16)0.0552 (18)0.0350 (16)0.0061 (14)0.0150 (13)0.0072 (13)
C90.0440 (16)0.0451 (16)0.0465 (18)0.0024 (13)0.0188 (13)0.0144 (13)
C100.0473 (17)0.0347 (14)0.0526 (19)0.0091 (12)0.0162 (14)0.0057 (13)
C110.0525 (18)0.0362 (15)0.057 (2)0.0146 (13)0.0129 (15)0.0034 (13)
C120.0393 (15)0.0383 (15)0.0369 (15)0.0046 (11)0.0069 (12)0.0014 (11)
C130.081 (2)0.063 (2)0.0414 (19)0.0055 (19)0.0151 (17)0.0133 (16)
C140.081 (3)0.066 (2)0.0362 (18)0.0190 (19)0.0007 (17)0.0011 (16)
C150.065 (2)0.054 (2)0.051 (2)0.0065 (17)0.0107 (16)0.0078 (16)
C160.0538 (18)0.0426 (16)0.051 (2)0.0052 (14)0.0020 (15)0.0002 (14)
C170.061 (2)0.0456 (17)0.0462 (19)0.0025 (15)0.0113 (15)0.0036 (14)
C180.0421 (16)0.0528 (18)0.055 (2)0.0031 (14)0.0107 (14)0.0121 (15)
C190.0441 (18)0.058 (2)0.084 (3)0.0136 (15)0.0133 (17)0.0142 (19)
C200.0464 (18)0.0453 (18)0.077 (3)0.0107 (14)0.0031 (16)0.0034 (17)
C210.0391 (15)0.0338 (15)0.057 (2)0.0004 (12)0.0026 (13)0.0009 (13)
C220.0316 (13)0.0317 (13)0.0396 (16)0.0043 (11)0.0006 (11)0.0016 (11)
C230.0340 (13)0.0300 (13)0.0330 (14)0.0089 (10)0.0007 (11)0.0028 (11)
C240.0436 (16)0.0362 (14)0.0327 (15)0.0108 (12)0.0022 (12)0.0042 (11)
C250.0531 (18)0.0465 (17)0.0410 (17)0.0109 (14)0.0047 (14)0.0134 (13)
C260.0464 (18)0.0407 (16)0.063 (2)0.0018 (14)0.0124 (15)0.0181 (15)
C270.0384 (14)0.0308 (13)0.0309 (14)0.0059 (11)0.0053 (11)0.0012 (11)
C280.0512 (17)0.0440 (16)0.0374 (16)0.0071 (13)0.0153 (13)0.0065 (13)
C290.0548 (18)0.0459 (17)0.0314 (15)0.0124 (14)0.0096 (13)0.0029 (12)
C300.0535 (19)0.0446 (17)0.057 (2)0.0101 (14)0.0080 (15)0.0073 (15)
C310.062 (2)0.0409 (16)0.0491 (19)0.0017 (14)0.0137 (15)0.0110 (14)
C320.068 (2)0.0382 (17)0.073 (3)0.0093 (15)0.0222 (18)0.0109 (16)
C330.062 (2)0.0423 (17)0.075 (3)0.0170 (15)0.0190 (18)0.0094 (16)
C340.0427 (15)0.0299 (13)0.0417 (16)0.0015 (11)0.0101 (12)0.0042 (12)
Cl10.0624 (5)0.0548 (5)0.0495 (5)0.0031 (4)0.0100 (4)0.0099 (4)
Cl20.0390 (4)0.0355 (3)0.0378 (4)0.0005 (3)0.0129 (3)0.0017 (3)
N10.0370 (12)0.0304 (11)0.0330 (12)0.0025 (9)0.0092 (9)0.0011 (9)
N20.0419 (13)0.0348 (11)0.0317 (12)0.0072 (10)0.0082 (10)0.0019 (9)
N30.0361 (12)0.0350 (12)0.0403 (14)0.0001 (10)0.0070 (10)0.0024 (10)
N40.0330 (11)0.0280 (11)0.0309 (12)0.0038 (8)0.0054 (9)0.0003 (8)
N50.0455 (14)0.0369 (12)0.0362 (13)0.0077 (10)0.0046 (10)0.0012 (10)
N60.0424 (13)0.0329 (12)0.0394 (14)0.0003 (10)0.0105 (10)0.0020 (10)
O10.098 (2)0.0762 (17)0.0574 (16)0.0310 (16)0.0201 (14)0.0083 (14)
O20.0461 (11)0.0398 (11)0.0353 (11)0.0070 (8)0.0063 (9)0.0018 (8)
O30.0490 (12)0.0427 (11)0.0591 (14)0.0064 (9)0.0277 (10)0.0052 (10)
O40.0644 (14)0.0554 (13)0.0409 (12)0.0072 (11)0.0135 (10)0.0092 (10)
O50.0689 (15)0.0610 (15)0.0807 (18)0.0316 (12)0.0357 (13)0.0232 (13)
O60.0808 (17)0.0791 (17)0.0607 (16)0.0412 (15)0.0188 (13)0.0191 (13)
O70.119 (3)0.123 (3)0.063 (2)0.016 (2)0.0161 (17)0.0431 (18)
O80.067 (2)0.260 (5)0.115 (3)0.034 (3)0.021 (2)0.117 (3)
O90.217 (5)0.220 (5)0.181 (5)0.126 (5)0.050 (4)0.049 (4)
O100.331 (7)0.161 (4)0.094 (3)0.145 (5)0.069 (4)0.068 (3)
Zn10.0430 (2)0.03160 (19)0.02842 (19)0.00084 (12)0.01094 (14)0.00178 (12)
Geometric parameters (Å, º) top
C1—N21.334 (4)C21—C221.412 (4)
C1—C21.382 (4)C21—C261.424 (5)
C1—H10.9300C22—N31.354 (3)
C2—C31.365 (4)C22—C231.431 (4)
C2—H20.9300C23—N41.365 (3)
C3—C41.401 (4)C23—C241.394 (4)
C3—H30.9300C24—C291.402 (4)
C4—C51.405 (4)C24—C251.418 (4)
C4—C81.427 (4)C25—C261.339 (5)
C5—N21.354 (3)C25—H250.9300
C5—C61.434 (4)C26—H260.9300
C6—N11.356 (3)C27—N41.328 (3)
C6—C71.411 (3)C27—C281.396 (4)
C7—C101.403 (4)C27—N61.434 (3)
C7—C91.421 (4)C28—C291.359 (4)
C8—C91.349 (4)C28—H280.9300
C8—H80.9300C29—H290.9300
C9—H90.9300C30—C331.340 (5)
C10—C111.348 (4)C30—C341.429 (4)
C10—H100.9300C30—H60.9300
C11—C121.395 (4)C31—C321.344 (5)
C11—H110.9300C31—N61.393 (4)
C12—N11.324 (3)C31—H310.9300
C12—N51.432 (4)C32—C331.395 (5)
C13—C141.342 (5)C32—H320.9300
C13—C171.433 (5)C33—H330.9300
C13—H130.9300C34—O21.241 (3)
C14—C151.398 (5)C34—N61.400 (4)
C14—H140.9300Cl1—O91.326 (4)
C15—C161.338 (4)Cl1—O81.369 (3)
C15—H150.9300Cl1—O101.377 (4)
C16—N51.368 (4)Cl1—O71.416 (3)
C16—H160.9300Cl2—O51.413 (2)
C17—O11.216 (4)Cl2—O61.423 (2)
C17—N51.403 (4)Cl2—O41.425 (2)
C18—N31.327 (4)Cl2—O31.4473 (19)
C18—C191.389 (5)N1—Zn12.160 (2)
C18—H180.9300N2—Zn12.089 (2)
C19—C201.341 (5)N3—Zn12.084 (2)
C19—H190.9300N4—Zn12.128 (2)
C20—C211.403 (4)O2—Zn12.0291 (19)
C20—H200.9300O3—Zn12.395 (2)
N2—C1—C2122.9 (3)C25—C26—C21121.2 (3)
N2—C1—H1118.5C25—C26—H26119.4
C2—C1—H1118.5C21—C26—H26119.4
C3—C2—C1119.8 (3)N4—C27—C28122.4 (2)
C3—C2—H2120.1N4—C27—N6119.2 (2)
C1—C2—H2120.1C28—C27—N6118.4 (2)
C2—C3—C4119.2 (3)C29—C28—C27119.5 (3)
C2—C3—H3120.4C29—C28—H28120.2
C4—C3—H3120.4C27—C28—H28120.2
C3—C4—C5117.5 (3)C28—C29—C24120.1 (3)
C3—C4—C8122.8 (3)C28—C29—H29120.0
C5—C4—C8119.7 (3)C24—C29—H29120.0
N2—C5—C4122.8 (2)C33—C30—C34123.0 (3)
N2—C5—C6117.6 (2)C33—C30—H6118.5
C4—C5—C6119.6 (2)C34—C30—H6118.5
N1—C6—C7122.4 (2)C32—C31—N6121.7 (3)
N1—C6—C5118.6 (2)C32—C31—H31119.2
C7—C6—C5119.0 (2)N6—C31—H31119.2
C10—C7—C6116.7 (3)C31—C32—C33119.8 (3)
C10—C7—C9123.5 (2)C31—C32—H32120.1
C6—C7—C9119.8 (3)C33—C32—H32120.1
C9—C8—C4120.6 (3)C30—C33—C32119.3 (3)
C9—C8—H8119.7C30—C33—H33120.4
C4—C8—H8119.7C32—C33—H33120.4
C8—C9—C7121.3 (3)O2—C34—N6123.5 (2)
C8—C9—H9119.4O2—C34—C30121.2 (3)
C7—C9—H9119.4N6—C34—C30115.4 (3)
C11—C10—C7120.6 (3)O9—Cl1—O8107.5 (4)
C11—C10—H10119.7O9—Cl1—O10106.8 (4)
C7—C10—H10119.7O8—Cl1—O10111.2 (3)
C10—C11—C12119.0 (3)O9—Cl1—O7109.8 (3)
C10—C11—H11120.5O8—Cl1—O7111.6 (2)
C12—C11—H11120.5O10—Cl1—O7109.8 (2)
N1—C12—C11123.1 (3)O5—Cl2—O6112.17 (18)
N1—C12—N5117.1 (2)O5—Cl2—O4108.84 (14)
C11—C12—N5119.7 (3)O6—Cl2—O4109.63 (15)
C14—C13—C17122.6 (3)O5—Cl2—O3109.85 (13)
C14—C13—H13118.7O6—Cl2—O3107.41 (14)
C17—C13—H13118.7O4—Cl2—O3108.88 (13)
C13—C14—C15120.3 (3)C12—N1—C6118.1 (2)
C13—C14—H14119.8C12—N1—Zn1131.17 (18)
C15—C14—H14119.8C6—N1—Zn1110.56 (16)
C16—C15—C14119.4 (3)C1—N2—C5117.8 (2)
C16—C15—H15120.3C1—N2—Zn1128.65 (19)
C14—C15—H15120.3C5—N2—Zn1113.59 (17)
C15—C16—N5120.8 (3)C18—N3—C22119.3 (3)
C15—C16—H16119.6C18—N3—Zn1127.9 (2)
N5—C16—H16119.6C22—N3—Zn1112.77 (17)
O1—C17—N5119.7 (3)C27—N4—C23117.6 (2)
O1—C17—C13126.6 (3)C27—N4—Zn1129.78 (18)
N5—C17—C13113.8 (3)C23—N4—Zn1111.17 (16)
N3—C18—C19121.6 (3)C16—N5—C17123.1 (3)
N3—C18—H18119.2C16—N5—C12118.4 (2)
C19—C18—H18119.2C17—N5—C12118.4 (2)
C20—C19—C18119.9 (3)C31—N6—C34119.7 (2)
C20—C19—H19120.0C31—N6—C27116.2 (2)
C18—C19—H19120.0C34—N6—C27124.0 (2)
C19—C20—C21120.9 (3)C34—O2—Zn1133.58 (19)
C19—C20—H20119.6Cl2—O3—Zn1135.05 (12)
C21—C20—H20119.6O2—Zn1—N3160.72 (8)
C20—C21—C22116.2 (3)O2—Zn1—N297.89 (8)
C20—C21—C26124.9 (3)N3—Zn1—N297.84 (9)
C22—C21—C26118.9 (3)O2—Zn1—N482.97 (8)
N3—C22—C21122.2 (3)N3—Zn1—N479.69 (8)
N3—C22—C23118.2 (2)N2—Zn1—N4170.52 (8)
C21—C22—C23119.6 (3)O2—Zn1—N192.99 (8)
N4—C23—C24123.6 (2)N3—Zn1—N1100.85 (8)
N4—C23—C22117.3 (2)N2—Zn1—N179.22 (8)
C24—C23—C22119.1 (2)N4—Zn1—N1110.20 (8)
C23—C24—C29116.5 (3)O2—Zn1—O385.91 (8)
C23—C24—C25120.0 (3)N3—Zn1—O384.52 (8)
C29—C24—C25123.5 (3)N2—Zn1—O384.69 (8)
C26—C25—C24121.1 (3)N4—Zn1—O385.96 (7)
C26—C25—H25119.4N1—Zn1—O3163.57 (8)
C24—C25—H25119.4
N2—C1—C2—C31.2 (5)N6—C27—N4—C23177.7 (2)
C1—C2—C3—C41.9 (5)C28—C27—N4—Zn1162.4 (2)
C2—C3—C4—C50.4 (4)N6—C27—N4—Zn117.5 (3)
C2—C3—C4—C8179.0 (3)C24—C23—N4—C272.9 (4)
C3—C4—C5—N21.8 (4)C22—C23—N4—C27177.5 (2)
C8—C4—C5—N2178.8 (3)C24—C23—N4—Zn1170.4 (2)
C3—C4—C5—C6177.1 (3)C22—C23—N4—Zn110.1 (3)
C8—C4—C5—C62.4 (4)C15—C16—N5—C170.6 (4)
N2—C5—C6—N13.4 (4)C15—C16—N5—C12176.8 (3)
C4—C5—C6—N1175.5 (2)O1—C17—N5—C16179.7 (3)
N2—C5—C6—C7179.2 (2)C13—C17—N5—C160.8 (4)
C4—C5—C6—C71.9 (4)O1—C17—N5—C123.6 (4)
N1—C6—C7—C102.1 (4)C13—C17—N5—C12177.0 (3)
C5—C6—C7—C10179.3 (2)N1—C12—N5—C1674.3 (3)
N1—C6—C7—C9176.6 (2)C11—C12—N5—C16102.5 (3)
C5—C6—C7—C90.7 (4)N1—C12—N5—C17109.3 (3)
C3—C4—C8—C9177.6 (3)C11—C12—N5—C1773.9 (4)
C5—C4—C8—C91.8 (4)C32—C31—N6—C349.1 (4)
C4—C8—C9—C70.6 (4)C32—C31—N6—C27168.1 (3)
C10—C7—C9—C8178.6 (3)O2—C34—N6—C31167.6 (3)
C6—C7—C9—C80.1 (4)C30—C34—N6—C3112.5 (4)
C6—C7—C10—C112.3 (4)O2—C34—N6—C2715.4 (4)
C9—C7—C10—C11176.3 (3)C30—C34—N6—C27164.4 (2)
C7—C10—C11—C120.1 (5)N4—C27—N6—C31153.0 (2)
C10—C11—C12—N12.7 (5)C28—C27—N6—C3127.1 (4)
C10—C11—C12—N5173.8 (3)N4—C27—N6—C3430.0 (4)
C17—C13—C14—C150.2 (5)C28—C27—N6—C34150.0 (3)
C13—C14—C15—C160.5 (5)N6—C34—O2—Zn113.4 (4)
C14—C15—C16—N50.0 (5)C30—C34—O2—Zn1166.7 (2)
C14—C13—C17—O1179.8 (4)O5—Cl2—O3—Zn143.3 (2)
C14—C13—C17—N50.4 (5)O6—Cl2—O3—Zn1165.51 (19)
N3—C18—C19—C200.3 (5)O4—Cl2—O3—Zn175.8 (2)
C18—C19—C20—C210.7 (5)C34—O2—Zn1—N345.0 (4)
C19—C20—C21—C220.5 (5)C34—O2—Zn1—N2170.5 (2)
C19—C20—C21—C26176.6 (3)C34—O2—Zn1—N419.0 (2)
C20—C21—C22—N30.1 (4)C34—O2—Zn1—N191.0 (2)
C26—C21—C22—N3177.4 (2)C34—O2—Zn1—O3105.4 (2)
C20—C21—C22—C23179.4 (2)C18—N3—Zn1—O2156.0 (3)
C26—C21—C22—C232.1 (4)C22—N3—Zn1—O220.7 (4)
N3—C22—C23—N45.7 (3)C18—N3—Zn1—N211.6 (2)
C21—C22—C23—N4174.8 (2)C22—N3—Zn1—N2165.17 (17)
N3—C22—C23—C24174.7 (2)C18—N3—Zn1—N4177.7 (2)
C21—C22—C23—C244.8 (4)C22—N3—Zn1—N45.57 (17)
N4—C23—C24—C294.8 (4)C18—N3—Zn1—N168.9 (2)
C22—C23—C24—C29175.7 (2)C22—N3—Zn1—N1114.38 (18)
N4—C23—C24—C25175.7 (2)C18—N3—Zn1—O395.4 (2)
C22—C23—C24—C253.9 (4)C22—N3—Zn1—O381.31 (18)
C23—C24—C25—C260.2 (4)C1—N2—Zn1—O294.4 (3)
C29—C24—C25—C26179.3 (3)C5—N2—Zn1—O286.92 (19)
C24—C25—C26—C212.6 (5)C1—N2—Zn1—N374.4 (3)
C20—C21—C26—C25175.4 (3)C5—N2—Zn1—N3104.27 (19)
C22—C21—C26—C251.6 (4)C1—N2—Zn1—N40.2 (7)
N4—C27—C28—C295.6 (4)C5—N2—Zn1—N4178.5 (4)
N6—C27—C28—C29174.5 (3)C1—N2—Zn1—N1174.0 (3)
C27—C28—C29—C243.4 (4)C5—N2—Zn1—N14.64 (18)
C23—C24—C29—C281.5 (4)C1—N2—Zn1—O39.3 (3)
C25—C24—C29—C28179.0 (3)C5—N2—Zn1—O3172.02 (19)
N6—C31—C32—C330.7 (5)C27—N4—Zn1—O22.4 (2)
C34—C30—C33—C320.9 (5)C23—N4—Zn1—O2163.13 (17)
C31—C32—C33—C303.4 (5)C27—N4—Zn1—N3173.9 (2)
C33—C30—C34—O2171.4 (3)C23—N4—Zn1—N38.39 (16)
C33—C30—C34—N68.8 (4)C27—N4—Zn1—N298.2 (5)
C11—C12—N1—C63.0 (4)C23—N4—Zn1—N267.3 (6)
N5—C12—N1—C6173.7 (2)C27—N4—Zn1—N188.2 (2)
C11—C12—N1—Zn1172.3 (2)C23—N4—Zn1—N1106.26 (16)
N5—C12—N1—Zn111.1 (4)C27—N4—Zn1—O388.7 (2)
C7—C6—N1—C120.5 (4)C23—N4—Zn1—O376.77 (16)
C5—C6—N1—C12176.8 (2)C12—N1—Zn1—O284.3 (2)
C7—C6—N1—Zn1175.66 (19)C6—N1—Zn1—O291.27 (17)
C5—C6—N1—Zn17.0 (3)C12—N1—Zn1—N382.2 (2)
C2—C1—N2—C50.9 (4)C6—N1—Zn1—N3102.23 (17)
C2—C1—N2—Zn1179.6 (2)C12—N1—Zn1—N2178.3 (3)
C4—C5—N2—C12.5 (4)C6—N1—Zn1—N26.21 (16)
C6—C5—N2—C1176.4 (2)C12—N1—Zn1—N40.6 (3)
C4—C5—N2—Zn1178.7 (2)C6—N1—Zn1—N4174.87 (16)
C6—C5—N2—Zn12.4 (3)C12—N1—Zn1—O3169.9 (2)
C19—C18—N3—C220.2 (4)C6—N1—Zn1—O35.6 (4)
C19—C18—N3—Zn1176.8 (2)Cl2—O3—Zn1—O242.73 (19)
C21—C22—N3—C180.5 (4)Cl2—O3—Zn1—N3120.5 (2)
C23—C22—N3—C18179.0 (2)Cl2—O3—Zn1—N2141.1 (2)
C21—C22—N3—Zn1177.5 (2)Cl2—O3—Zn1—N440.50 (19)
C23—C22—N3—Zn12.0 (3)Cl2—O3—Zn1—N1129.4 (2)
C28—C27—N4—C232.4 (4)

Experimental details

Crystal data
Chemical formula[Zn(ClO4)(C17H11N3O)2]ClO4
Mr810.85
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)12.998 (2), 16.741 (3), 14.680 (3)
β (°) 100.068 (2)
V3)3145.2 (10)
Z4
Radiation typeMo Kα
µ (mm1)1.03
Crystal size (mm)0.45 × 0.38 × 0.26
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.655, 0.776
No. of measured, independent and
observed [I > 2σ(I)] reflections
16722, 6163, 5005
Rint0.028
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.130, 1.08
No. of reflections6163
No. of parameters480
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.82, 0.63

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

 

Acknowledgements

The authors thank the Research Project of `SUST Spring Bud' for support (No. 2008BWZ056).

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLiu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58–m60.  Web of Science CSD CrossRef IUCr Journals 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

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