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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Jul 19;64(Pt 8):m1047. doi: 10.1107/S1600536808022034

Bis{μ-2-(1H-indol-3-yl)-N′-[1-(5-methyl-2-oxidophen­yl)ethyl­idene]­aceto­hydraz­idato}bis­[aqua­zinc(II)] dimethyl sulfoxide tetra­solvate

Kadir Zuraini a, Hapipah M Ali a, Subramaniam Puvaneswary a, Ward T Robinson a, Seik Weng Ng a,*
PMCID: PMC2961965  PMID: 21203035

Abstract

The dinuclear title compound, [Zn2(C19H17N3O2)2(H2O)2]·4C2H6OS, lies about a center of inversion. The deprotonated monoanion O,N,O-chelates the Zn atom; the hydr­oxy O atom also engages in bonding to the symmetry-related Zn atom so that one N and three O atoms form a square around the metal. The coordination geometry is square-pyramidal, with the apical site occupied by a water mol­ecule. Hydrogen bonds, with the water mol­ecule serving as donor atom, lead to the formation of a linear chain motif. There is an N—H⋯O hydrogen bond between the complex molecule and solvent O atom.

Related literature

For the structure of a similar Schiff base ligand, see: Ali et al. (2008 ▶).graphic file with name e-64-m1047-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C19H17N3O2)2(H2O)2]·4C2H6OS

  • M r = 1118.00

  • Triclinic, Inline graphic

  • a = 8.5271 (2) Å

  • b = 8.8849 (3) Å

  • c = 16.8279 (5) Å

  • α = 85.519 (2)°

  • β = 84.920 (2)°

  • γ = 84.251 (2)°

  • V = 1260.44 (6) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.18 mm−1

  • T = 100 (2) K

  • 0.19 × 0.03 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.807, T max = 0.966

  • 13526 measured reflections

  • 5739 independent reflections

  • 3700 reflections with I > 2σ(I)

  • R int = 0.076

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056

  • wR(F 2) = 0.157

  • S = 0.99

  • 5739 reflections

  • 313 parameters

  • H-atom parameters constrained

  • Δρmax = 1.18 e Å−3

  • Δρmin = −1.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022034/si2100sup1.cif

e-64-m1047-sup1.cif (24.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022034/si2100Isup2.hkl

e-64-m1047-Isup2.hkl (280.9KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1W—H1W1⋯O3 0.84 1.80 2.608 (4) 161
O1W—H1W2⋯N2i 0.84 1.87 2.703 (4) 173
N3—H3N⋯O4 0.88 1.95 2.822 (5) 172
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Symmetry code: (i) Inline graphic.

Acknowledgments

We thank the Science Fund (12-02-03-2031, 12-02-03-2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

The present study continues with a study on 1-(2-hydroxy-5-methylphenyl)ethanone [(1H-3-indolyl)acetyl]hydrazone (Ali et al., 2008). The present study reports the zinc derivative of a similar ligand (Scheme I, Fig. 1). The dinuclear compound lies about a center-of-inversion. The deprotonated monoanion O,N,O chelates to the Zn atom; the hydroxy oxygen atom also engages in bonding to the symmetry-related Zn atom so that one nitrogen and oxygen atoms comprise a square around the metal. The geometry is a square pyramid, with the apical site occupied by a water molecule. Hydrogen bonds, with the water molecule serving as donor atom, leads to the formation of a linear chain motif.

Experimental

Indole-3- acetic acid hydrazide (0.55 g, 4 mmol) and 5-methyl-2-hydroxyacetophenone (0.52 g, 4 mmol) were heated in ethanol for 2 h. The solvent was removed to give the Schiff base. The ligand (0.55 g, 4 mmol) and zinc acetate (0.26 g, 2 mmol) were dissolved in basified ethanol and heated for 5 h. The yellow solid was that was obtained was recrystallized from DMSO.

Refinement

Carbon and nitrogen-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å, N–H 0.88 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Ueq(C). The water H-atoms were placed in chemically sensible positions on the basis of hydrogen bonding, but were not refined.

The final difference Fourier map had a large peak/deep hole near Zn1.

Figures

Fig. 1.

Fig. 1.

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Thermal ellipsoid plot (Barbour, 2001) plot of the dinuclear compound at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The compound lies about a center of inversion, and unlabeled atoms are related to their labeled equivalents by 1 – x, 1 – y, 1 – z.

Crystal data

[Zn2(C19H17N3O2)2(H2O)2]·4C2H6OS Z = 1
Mr = 1118.00 F000 = 584
Triclinic, P1 Dx = 1.473 Mg m−3
Hall symbol: -P 1 Mo Kα radiation λ = 0.71073 Å
a = 8.5271 (2) Å Cell parameters from 2055 reflections
b = 8.8849 (3) Å θ = 2.4–21.0º
c = 16.8279 (5) Å µ = 1.18 mm−1
α = 85.519 (2)º T = 100 (2) K
β = 84.920 (2)º Block, yellow
γ = 84.251 (2)º 0.19 × 0.03 × 0.03 mm
V = 1260.44 (6) Å3
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Data collection

Bruker SMART APEX diffractometer 5739 independent reflections
Radiation source: fine-focus sealed tube 3700 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.077
T = 100(2) K θmax = 27.5º
ω scans θmin = 1.2º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996) h = −11→11
Tmin = 0.807, Tmax = 0.966 k = −11→9
13526 measured reflections l = −21→21
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056 H-atom parameters constrained
wR(F2) = 0.157   w = 1/[σ2(Fo2) + (0.0772P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99 (Δ/σ)max = 0.001
5739 reflections Δρmax = 1.18 e Å−3
313 parameters Δρmin = −1.24 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Zn1 0.32563 (6) 0.51110 (6) 0.47468 (3) 0.01466 (16)
S2 0.28628 (14) 0.71165 (15) −0.05107 (7) 0.0237 (3)
S1 0.51759 (13) 0.81274 (15) 0.61958 (7) 0.0223 (3)
O1 0.4553 (3) 0.4370 (4) 0.56890 (17) 0.0159 (7)
O2 0.2019 (3) 0.5011 (4) 0.37781 (18) 0.0213 (7)
O3 0.3597 (4) 0.8802 (4) 0.5929 (2) 0.0338 (9)
O4 0.3710 (4) 0.6688 (4) 0.02322 (19) 0.0237 (8)
O1W 0.2288 (3) 0.7174 (4) 0.49948 (18) 0.0198 (7)
H1W1 0.2774 0.7502 0.5348 0.030*
H1W2 0.1334 0.7129 0.5162 0.030*
N1 0.1821 (4) 0.3402 (4) 0.5139 (2) 0.0135 (8)
N2 0.0796 (4) 0.3130 (4) 0.4563 (2) 0.0147 (8)
N3 0.2308 (5) 0.4574 (5) 0.1345 (2) 0.0264 (10)
H3N 0.2808 0.5159 0.0981 0.032*
C1 0.4099 (5) 0.3577 (5) 0.6363 (2) 0.0144 (9)
C2 0.4983 (5) 0.3584 (5) 0.7028 (2) 0.0179 (10)
H2 0.5895 0.4127 0.6978 0.021*
C3 0.4569 (5) 0.2829 (5) 0.7751 (3) 0.0180 (10)
H3 0.5204 0.2848 0.8185 0.022*
C4 0.3218 (5) 0.2035 (5) 0.7849 (2) 0.0173 (9)
C5 0.2384 (5) 0.1992 (5) 0.7189 (2) 0.0158 (9)
H5 0.1486 0.1428 0.7247 0.019*
C6 0.2765 (5) 0.2724 (5) 0.6434 (2) 0.0148 (9)
C7 0.2737 (6) 0.1222 (6) 0.8645 (3) 0.0255 (11)
H7A 0.1851 0.0629 0.8584 0.038*
H7B 0.2415 0.1969 0.9041 0.038*
H7C 0.3635 0.0543 0.8824 0.038*
C8 0.1777 (5) 0.2507 (5) 0.5786 (2) 0.0139 (9)
C9 0.0720 (5) 0.1235 (5) 0.5894 (3) 0.0201 (10)
H9A 0.0518 0.0925 0.5369 0.030*
H9B −0.0285 0.1580 0.6182 0.030*
H9C 0.1237 0.0371 0.6200 0.030*
C10 0.1006 (5) 0.4035 (5) 0.3904 (3) 0.0166 (9)
C11 −0.0086 (5) 0.3896 (5) 0.3254 (2) 0.0170 (10)
H11A −0.0626 0.2958 0.3372 0.020*
H11B −0.0906 0.4768 0.3252 0.020*
C12 0.0803 (5) 0.3853 (5) 0.2444 (2) 0.0166 (9)
C13 0.1430 (6) 0.5047 (6) 0.2012 (3) 0.0244 (11)
H13 0.1275 0.6067 0.2156 0.029*
C14 0.1322 (5) 0.2547 (5) 0.2012 (2) 0.0164 (9)
C15 0.1120 (5) 0.0994 (6) 0.2144 (3) 0.0207 (10)
H15 0.0459 0.0636 0.2588 0.025*
C16 0.1893 (6) 0.0001 (6) 0.1621 (3) 0.0265 (11)
H16 0.1765 −0.1051 0.1710 0.032*
C17 0.2869 (5) 0.0515 (6) 0.0958 (3) 0.0261 (11)
H17 0.3397 −0.0200 0.0610 0.031*
C18 0.3076 (5) 0.2019 (6) 0.0802 (3) 0.0230 (11)
H18 0.3729 0.2365 0.0351 0.028*
C19 0.2282 (5) 0.3032 (6) 0.1335 (3) 0.0193 (10)
C20 0.6333 (6) 0.9686 (6) 0.6179 (3) 0.0312 (12)
H20A 0.6492 1.0129 0.5630 0.047*
H20B 0.7361 0.9336 0.6380 0.047*
H20C 0.5784 1.0453 0.6519 0.047*
C21 0.4833 (7) 0.7774 (8) 0.7244 (3) 0.0400 (15)
H21A 0.4050 0.7035 0.7359 0.060*
H21B 0.4436 0.8722 0.7485 0.060*
H21C 0.5825 0.7370 0.7468 0.060*
C22 0.2380 (7) 0.5408 (7) −0.0869 (3) 0.0395 (14)
H22A 0.3354 0.4786 −0.1030 0.059*
H22B 0.1751 0.5646 −0.1330 0.059*
H22C 0.1768 0.4848 −0.0444 0.059*
C23 0.0906 (6) 0.7843 (7) −0.0178 (3) 0.0329 (13)
H23A 0.0953 0.8749 0.0113 0.049*
H23B 0.0403 0.7071 0.0177 0.049*
H23C 0.0287 0.8109 −0.0641 0.049*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Zn1 0.0079 (2) 0.0202 (3) 0.0158 (3) −0.0058 (2) 0.00131 (18) 0.0025 (2)
S2 0.0200 (6) 0.0270 (7) 0.0230 (6) −0.0063 (5) 0.0020 (5) 0.0058 (5)
S1 0.0161 (5) 0.0233 (7) 0.0278 (6) 0.0003 (5) −0.0040 (5) −0.0040 (5)
O1 0.0111 (14) 0.0222 (19) 0.0141 (14) −0.0070 (13) 0.0009 (12) 0.0050 (13)
O2 0.0153 (15) 0.030 (2) 0.0195 (16) −0.0110 (14) 0.0012 (13) 0.0041 (14)
O3 0.0222 (18) 0.035 (2) 0.047 (2) 0.0040 (16) −0.0174 (17) −0.0109 (18)
O4 0.0163 (16) 0.025 (2) 0.0291 (18) −0.0088 (14) 0.0001 (14) 0.0103 (15)
O1W 0.0107 (14) 0.0250 (19) 0.0238 (16) −0.0057 (13) −0.0002 (13) 0.0012 (14)
N1 0.0096 (16) 0.017 (2) 0.0142 (17) −0.0018 (15) 0.0008 (14) −0.0016 (15)
N2 0.0096 (16) 0.017 (2) 0.0178 (18) −0.0033 (15) 0.0011 (14) −0.0021 (15)
N3 0.034 (2) 0.028 (3) 0.018 (2) −0.014 (2) −0.0004 (18) 0.0056 (18)
C1 0.0089 (19) 0.016 (2) 0.017 (2) −0.0029 (17) 0.0038 (16) 0.0011 (17)
C2 0.011 (2) 0.024 (3) 0.019 (2) −0.0063 (19) 0.0049 (17) −0.0035 (19)
C3 0.016 (2) 0.021 (3) 0.017 (2) −0.0057 (19) −0.0003 (18) 0.0014 (18)
C4 0.019 (2) 0.019 (3) 0.013 (2) −0.0018 (19) 0.0021 (17) 0.0032 (18)
C5 0.010 (2) 0.017 (3) 0.019 (2) −0.0036 (18) 0.0036 (17) 0.0028 (18)
C6 0.0098 (19) 0.015 (2) 0.019 (2) −0.0030 (17) 0.0002 (17) 0.0018 (18)
C7 0.026 (3) 0.028 (3) 0.022 (2) −0.010 (2) 0.000 (2) 0.006 (2)
C8 0.0078 (19) 0.013 (2) 0.019 (2) −0.0016 (17) 0.0057 (16) 0.0034 (18)
C9 0.014 (2) 0.024 (3) 0.023 (2) −0.009 (2) −0.0042 (18) 0.003 (2)
C10 0.0089 (19) 0.021 (3) 0.020 (2) −0.0030 (18) 0.0020 (17) −0.0019 (19)
C11 0.0093 (19) 0.024 (3) 0.018 (2) −0.0017 (19) 0.0008 (17) −0.0018 (19)
C12 0.014 (2) 0.022 (3) 0.014 (2) −0.0057 (19) −0.0026 (17) 0.0037 (18)
C13 0.031 (3) 0.022 (3) 0.021 (2) −0.007 (2) −0.007 (2) 0.003 (2)
C14 0.011 (2) 0.024 (3) 0.015 (2) −0.0040 (19) −0.0031 (17) 0.0025 (18)
C15 0.018 (2) 0.024 (3) 0.020 (2) −0.006 (2) −0.0002 (18) −0.0007 (19)
C16 0.027 (3) 0.018 (3) 0.035 (3) −0.004 (2) −0.007 (2) 0.000 (2)
C17 0.021 (2) 0.030 (3) 0.028 (3) −0.001 (2) −0.002 (2) −0.010 (2)
C18 0.012 (2) 0.039 (3) 0.019 (2) −0.006 (2) 0.0002 (18) −0.005 (2)
C19 0.015 (2) 0.028 (3) 0.016 (2) −0.008 (2) −0.0007 (17) 0.0033 (19)
C20 0.029 (3) 0.027 (3) 0.039 (3) −0.002 (2) −0.009 (2) 0.000 (2)
C21 0.031 (3) 0.058 (4) 0.031 (3) −0.010 (3) −0.001 (2) 0.005 (3)
C22 0.048 (4) 0.035 (4) 0.036 (3) −0.004 (3) −0.003 (3) −0.009 (3)
C23 0.020 (3) 0.036 (3) 0.043 (3) 0.002 (2) −0.009 (2) −0.005 (3)
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Geometric parameters (Å, °)

Zn1—O1 2.043 (3) C7—H7B 0.9800
Zn1—O1i 2.029 (3) C7—H7C 0.9800
Zn1—O2 2.031 (3) C8—C9 1.506 (6)
Zn1—O1w 1.993 (3) C9—H9A 0.9800
Zn1—N1 2.077 (4) C9—H9B 0.9800
Zn1—Zn1i 3.1485 (9) C9—H9C 0.9800
S2—O4 1.503 (3) C10—C11 1.518 (5)
S2—C22 1.775 (6) C11—C12 1.502 (6)
S2—C23 1.786 (5) C11—H11A 0.9900
S1—O3 1.509 (3) C11—H11B 0.9900
S1—C21 1.771 (5) C12—C13 1.365 (6)
S1—C20 1.776 (5) C12—C14 1.428 (6)
O1—C1 1.335 (5) C13—H13 0.9500
O1—Zn1i 2.029 (3) C14—C15 1.406 (6)
O2—C10 1.277 (5) C14—C19 1.408 (6)
O1W—H1W1 0.8400 C15—C16 1.374 (7)
O1W—H1W2 0.8400 C15—H15 0.9500
N1—C8 1.297 (5) C16—C17 1.408 (7)
N1—N2 1.410 (4) C16—H16 0.9500
N2—C10 1.328 (6) C17—C18 1.368 (7)
N3—C13 1.363 (6) C17—H17 0.9500
N3—C19 1.374 (6) C18—C19 1.404 (7)
N3—H3N 0.8800 C18—H18 0.9500
C1—C2 1.404 (6) C20—H20A 0.9800
C1—C6 1.420 (6) C20—H20B 0.9800
C2—C3 1.377 (6) C20—H20C 0.9800
C2—H2 0.9500 C21—H21A 0.9800
C3—C4 1.401 (6) C21—H21B 0.9800
C3—H3 0.9500 C21—H21C 0.9800
C4—C5 1.375 (6) C22—H22A 0.9800
C4—C7 1.515 (6) C22—H22B 0.9800
C5—C6 1.408 (6) C22—H22C 0.9800
C5—H5 0.9500 C23—H23A 0.9800
C6—C8 1.472 (5) C23—H23B 0.9800
C7—H7A 0.9800 C23—H23C 0.9800
O1—Zn1—O1i 78.7 (1) C8—C9—H9B 109.5
O1—Zn1—O2 158.8 (1) H9A—C9—H9B 109.5
O1—Zn1—O1w 105.3 (1) C8—C9—H9C 109.5
O1—Zn1—N1 86.3 (1) H9A—C9—H9C 109.5
O1i—Zn1—O2 106.0 (1) H9B—C9—H9C 109.5
O1i—Zn1—O1w 99.5 (1) O2—C10—N2 126.0 (4)
O1i—Zn1—N1 146.5 (1) O2—C10—C11 118.0 (4)
O2—Zn1—O1w 94.5 (1) N2—C10—C11 116.0 (4)
O2—Zn1—N1 78.7 (1) C12—C11—C10 111.6 (3)
O1W—Zn1—N1 113.4 (1) C12—C11—H11A 109.3
O1W—Zn1—Zn1i 106.07 (8) C10—C11—H11A 109.3
O1i—Zn1—Zn1i 39.51 (8) C12—C11—H11B 109.3
O2—Zn1—Zn1i 141.51 (9) C10—C11—H11B 109.3
O1—Zn1—Zn1i 39.19 (8) H11A—C11—H11B 108.0
N1—Zn1—Zn1i 119.67 (10) C13—C12—C14 106.0 (4)
O4—S2—C22 107.0 (2) C13—C12—C11 126.2 (4)
O4—S2—C23 106.1 (2) C14—C12—C11 127.4 (4)
C22—S2—C23 97.8 (3) N3—C13—C12 110.7 (5)
O3—S1—C21 104.4 (2) N3—C13—H13 124.7
O3—S1—C20 105.1 (2) C12—C13—H13 124.7
C21—S1—C20 99.1 (3) C15—C14—C19 118.5 (4)
C1—O1—Zn1i 129.8 (2) C15—C14—C12 134.2 (4)
C1—O1—Zn1 128.3 (2) C19—C14—C12 107.2 (4)
Zn1i—O1—Zn1 101.30 (12) C16—C15—C14 119.1 (4)
C10—O2—Zn1 111.6 (3) C16—C15—H15 120.4
Zn1—O1W—H1W1 109.5 C14—C15—H15 120.4
Zn1—O1W—H1W2 109.5 C15—C16—C17 121.1 (5)
H1W1—O1W—H1W2 109.5 C15—C16—H16 119.4
C8—N1—N2 116.0 (4) C17—C16—H16 119.4
C8—N1—Zn1 131.5 (3) C18—C17—C16 121.5 (5)
N2—N1—Zn1 112.4 (3) C18—C17—H17 119.2
C10—N2—N1 111.2 (3) C16—C17—H17 119.2
C13—N3—C19 108.6 (4) C17—C18—C19 117.2 (4)
C13—N3—H3N 125.7 C17—C18—H18 121.4
C19—N3—H3N 125.7 C19—C18—H18 121.4
O1—C1—C2 118.6 (4) N3—C19—C18 130.0 (4)
O1—C1—C6 122.8 (4) N3—C19—C14 107.5 (4)
C2—C1—C6 118.6 (4) C18—C19—C14 122.5 (5)
C3—C2—C1 122.1 (4) S1—C20—H20A 109.5
C3—C2—H2 118.9 S1—C20—H20B 109.5
C1—C2—H2 118.9 H20A—C20—H20B 109.5
C2—C3—C4 120.4 (4) S1—C20—H20C 109.5
C2—C3—H3 119.8 H20A—C20—H20C 109.5
C4—C3—H3 119.8 H20B—C20—H20C 109.5
C5—C4—C3 117.2 (4) S1—C21—H21A 109.5
C5—C4—C7 121.9 (4) S1—C21—H21B 109.5
C3—C4—C7 120.9 (4) H21A—C21—H21B 109.5
C4—C5—C6 124.7 (4) S1—C21—H21C 109.5
C4—C5—H5 117.7 H21A—C21—H21C 109.5
C6—C5—H5 117.7 H21B—C21—H21C 109.5
C5—C6—C1 116.8 (4) S2—C22—H22A 109.5
C5—C6—C8 117.3 (4) S2—C22—H22B 109.5
C1—C6—C8 125.8 (4) H22A—C22—H22B 109.5
C4—C7—H7A 109.5 S2—C22—H22C 109.5
C4—C7—H7B 109.5 H22A—C22—H22C 109.5
H7A—C7—H7B 109.5 H22B—C22—H22C 109.5
C4—C7—H7C 109.5 S2—C23—H23A 109.5
H7A—C7—H7C 109.5 S2—C23—H23B 109.5
H7B—C7—H7C 109.5 H23A—C23—H23B 109.5
N1—C8—C6 120.3 (4) S2—C23—H23C 109.5
N1—C8—C9 121.1 (4) H23A—C23—H23C 109.5
C6—C8—C9 118.6 (4) H23B—C23—H23C 109.5
C8—C9—H9A 109.5
O1W—Zn1—O1—C1 91.0 (4) C2—C1—C6—C5 2.7 (6)
O1i—Zn1—O1—C1 −172.2 (4) O1—C1—C6—C8 4.2 (7)
O2—Zn1—O1—C1 −66.9 (5) C2—C1—C6—C8 −175.6 (4)
N1—Zn1—O1—C1 −22.3 (4) N2—N1—C8—C6 −178.2 (4)
Zn1i—Zn1—O1—C1 −172.2 (4) Zn1—N1—C8—C6 6.6 (6)
O1W—Zn1—O1—Zn1i −96.87 (14) N2—N1—C8—C9 1.6 (6)
O1i—Zn1—O1—Zn1i 0.0 Zn1—N1—C8—C9 −173.6 (3)
O2—Zn1—O1—Zn1i 105.2 (3) C5—C6—C8—N1 164.2 (4)
N1—Zn1—O1—Zn1i 149.86 (15) C1—C6—C8—N1 −17.5 (7)
O1W—Zn1—O2—C10 −111.0 (3) C5—C6—C8—C9 −15.6 (6)
O1i—Zn1—O2—C10 147.8 (3) C1—C6—C8—C9 162.7 (4)
O1—Zn1—O2—C10 47.6 (5) Zn1—O2—C10—N2 −2.8 (6)
N1—Zn1—O2—C10 2.0 (3) Zn1—O2—C10—C11 176.2 (3)
Zn1i—Zn1—O2—C10 126.0 (3) N1—N2—C10—O2 1.7 (6)
O1W—Zn1—N1—C8 −95.9 (4) N1—N2—C10—C11 −177.3 (3)
O1i—Zn1—N1—C8 72.1 (5) O2—C10—C11—C12 45.9 (6)
O2—Zn1—N1—C8 174.1 (4) N2—C10—C11—C12 −135.0 (4)
O1—Zn1—N1—C8 9.1 (4) C10—C11—C12—C13 −72.6 (6)
Zn1i—Zn1—N1—C8 30.5 (4) C10—C11—C12—C14 99.6 (5)
O1W—Zn1—N1—N2 88.7 (3) C19—N3—C13—C12 −0.7 (5)
O1i—Zn1—N1—N2 −103.2 (3) C14—C12—C13—N3 −0.3 (5)
O2—Zn1—N1—N2 −1.2 (2) C11—C12—C13—N3 173.2 (4)
O1—Zn1—N1—N2 −166.2 (3) C13—C12—C14—C15 178.4 (5)
Zn1i—Zn1—N1—N2 −144.8 (2) C11—C12—C14—C15 4.9 (7)
C8—N1—N2—C10 −175.8 (4) C13—C12—C14—C19 1.2 (4)
Zn1—N1—N2—C10 0.3 (4) C11—C12—C14—C19 −172.3 (4)
Zn1i—O1—C1—C2 29.5 (6) C19—C14—C15—C16 1.5 (6)
Zn1—O1—C1—C2 −160.5 (3) C12—C14—C15—C16 −175.4 (4)
Zn1i—O1—C1—C6 −150.3 (3) C14—C15—C16—C17 −0.4 (7)
Zn1—O1—C1—C6 19.7 (6) C15—C16—C17—C18 −0.7 (7)
O1—C1—C2—C3 178.2 (4) C16—C17—C18—C19 0.5 (6)
C6—C1—C2—C3 −2.0 (7) C13—N3—C19—C18 −175.9 (4)
C1—C2—C3—C4 −0.9 (7) C13—N3—C19—C14 1.4 (5)
C2—C3—C4—C5 2.8 (7) C17—C18—C19—N3 177.6 (4)
C2—C3—C4—C7 −179.0 (4) C17—C18—C19—C14 0.7 (6)
C3—C4—C5—C6 −2.0 (7) C15—C14—C19—N3 −179.3 (4)
C7—C4—C5—C6 179.8 (4) C12—C14—C19—N3 −1.6 (4)
C4—C5—C6—C1 −0.8 (7) C15—C14—C19—C18 −1.8 (6)
C4—C5—C6—C8 177.7 (4) C12—C14—C19—C18 175.9 (4)
O1—C1—C6—C5 −177.5 (4)
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Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O1W—H1W1···O3 0.84 1.80 2.608 (4) 161
O1W—H1W2···N2ii 0.84 1.87 2.703 (4) 173
N3—H3N···O4 0.88 1.95 2.822 (5) 172
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Symmetry codes: (ii) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2100).

References

  1. Ali, H. M., Zuraini, K., Wan Jeffrey, B., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, o912. [DOI] [PMC free article] [PubMed]
  2. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  3. Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  5. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  6. Westrip, S. P. (2008). publCIF In preparation.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022034/si2100sup1.cif

e-64-m1047-sup1.cif (24.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022034/si2100Isup2.hkl

e-64-m1047-Isup2.hkl (280.9KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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