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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1047.
Published online 2008 July 19. doi:  10.1107/S1600536808022034
PMCID: PMC2961965

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

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 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1047-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C19H17N3O2)2(H2O)2]·4C2H6OS
  • M r = 1118.00
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1047-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.
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 ...

Crystal data

[Zn2(C19H17N3O2)2(H2O)2]·4C2H6OSZ = 1
Mr = 1118.00F000 = 584
Triclinic, P1Dx = 1.473 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.5271 (2) ÅCell parameters from 2055 reflections
b = 8.8849 (3) Åθ = 2.4–21.0º
c = 16.8279 (5) ŵ = 1.18 mm1
α = 85.519 (2)ºT = 100 (2) K
β = 84.920 (2)ºBlock, yellow
γ = 84.251 (2)º0.19 × 0.03 × 0.03 mm
V = 1260.44 (6) Å3

Data collection

Bruker SMART APEX diffractometer5739 independent reflections
Radiation source: fine-focus sealed tube3700 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.077
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.2º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.807, Tmax = 0.966k = −11→9
13526 measured reflectionsl = −21→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-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 reflectionsΔρmax = 1.18 e Å3
313 parametersΔρmin = −1.24 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Zn10.32563 (6)0.51110 (6)0.47468 (3)0.01466 (16)
S20.28628 (14)0.71165 (15)−0.05107 (7)0.0237 (3)
S10.51759 (13)0.81274 (15)0.61958 (7)0.0223 (3)
O10.4553 (3)0.4370 (4)0.56890 (17)0.0159 (7)
O20.2019 (3)0.5011 (4)0.37781 (18)0.0213 (7)
O30.3597 (4)0.8802 (4)0.5929 (2)0.0338 (9)
O40.3710 (4)0.6688 (4)0.02322 (19)0.0237 (8)
O1W0.2288 (3)0.7174 (4)0.49948 (18)0.0198 (7)
H1W10.27740.75020.53480.030*
H1W20.13340.71290.51620.030*
N10.1821 (4)0.3402 (4)0.5139 (2)0.0135 (8)
N20.0796 (4)0.3130 (4)0.4563 (2)0.0147 (8)
N30.2308 (5)0.4574 (5)0.1345 (2)0.0264 (10)
H3N0.28080.51590.09810.032*
C10.4099 (5)0.3577 (5)0.6363 (2)0.0144 (9)
C20.4983 (5)0.3584 (5)0.7028 (2)0.0179 (10)
H20.58950.41270.69780.021*
C30.4569 (5)0.2829 (5)0.7751 (3)0.0180 (10)
H30.52040.28480.81850.022*
C40.3218 (5)0.2035 (5)0.7849 (2)0.0173 (9)
C50.2384 (5)0.1992 (5)0.7189 (2)0.0158 (9)
H50.14860.14280.72470.019*
C60.2765 (5)0.2724 (5)0.6434 (2)0.0148 (9)
C70.2737 (6)0.1222 (6)0.8645 (3)0.0255 (11)
H7A0.18510.06290.85840.038*
H7B0.24150.19690.90410.038*
H7C0.36350.05430.88240.038*
C80.1777 (5)0.2507 (5)0.5786 (2)0.0139 (9)
C90.0720 (5)0.1235 (5)0.5894 (3)0.0201 (10)
H9A0.05180.09250.53690.030*
H9B−0.02850.15800.61820.030*
H9C0.12370.03710.62000.030*
C100.1006 (5)0.4035 (5)0.3904 (3)0.0166 (9)
C11−0.0086 (5)0.3896 (5)0.3254 (2)0.0170 (10)
H11A−0.06260.29580.33720.020*
H11B−0.09060.47680.32520.020*
C120.0803 (5)0.3853 (5)0.2444 (2)0.0166 (9)
C130.1430 (6)0.5047 (6)0.2012 (3)0.0244 (11)
H130.12750.60670.21560.029*
C140.1322 (5)0.2547 (5)0.2012 (2)0.0164 (9)
C150.1120 (5)0.0994 (6)0.2144 (3)0.0207 (10)
H150.04590.06360.25880.025*
C160.1893 (6)0.0001 (6)0.1621 (3)0.0265 (11)
H160.1765−0.10510.17100.032*
C170.2869 (5)0.0515 (6)0.0958 (3)0.0261 (11)
H170.3397−0.02000.06100.031*
C180.3076 (5)0.2019 (6)0.0802 (3)0.0230 (11)
H180.37290.23650.03510.028*
C190.2282 (5)0.3032 (6)0.1335 (3)0.0193 (10)
C200.6333 (6)0.9686 (6)0.6179 (3)0.0312 (12)
H20A0.64921.01290.56300.047*
H20B0.73610.93360.63800.047*
H20C0.57841.04530.65190.047*
C210.4833 (7)0.7774 (8)0.7244 (3)0.0400 (15)
H21A0.40500.70350.73590.060*
H21B0.44360.87220.74850.060*
H21C0.58250.73700.74680.060*
C220.2380 (7)0.5408 (7)−0.0869 (3)0.0395 (14)
H22A0.33540.4786−0.10300.059*
H22B0.17510.5646−0.13300.059*
H22C0.17680.4848−0.04440.059*
C230.0906 (6)0.7843 (7)−0.0178 (3)0.0329 (13)
H23A0.09530.87490.01130.049*
H23B0.04030.70710.01770.049*
H23C0.02870.8109−0.06410.049*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0079 (2)0.0202 (3)0.0158 (3)−0.0058 (2)0.00131 (18)0.0025 (2)
S20.0200 (6)0.0270 (7)0.0230 (6)−0.0063 (5)0.0020 (5)0.0058 (5)
S10.0161 (5)0.0233 (7)0.0278 (6)0.0003 (5)−0.0040 (5)−0.0040 (5)
O10.0111 (14)0.0222 (19)0.0141 (14)−0.0070 (13)0.0009 (12)0.0050 (13)
O20.0153 (15)0.030 (2)0.0195 (16)−0.0110 (14)0.0012 (13)0.0041 (14)
O30.0222 (18)0.035 (2)0.047 (2)0.0040 (16)−0.0174 (17)−0.0109 (18)
O40.0163 (16)0.025 (2)0.0291 (18)−0.0088 (14)0.0001 (14)0.0103 (15)
O1W0.0107 (14)0.0250 (19)0.0238 (16)−0.0057 (13)−0.0002 (13)0.0012 (14)
N10.0096 (16)0.017 (2)0.0142 (17)−0.0018 (15)0.0008 (14)−0.0016 (15)
N20.0096 (16)0.017 (2)0.0178 (18)−0.0033 (15)0.0011 (14)−0.0021 (15)
N30.034 (2)0.028 (3)0.018 (2)−0.014 (2)−0.0004 (18)0.0056 (18)
C10.0089 (19)0.016 (2)0.017 (2)−0.0029 (17)0.0038 (16)0.0011 (17)
C20.011 (2)0.024 (3)0.019 (2)−0.0063 (19)0.0049 (17)−0.0035 (19)
C30.016 (2)0.021 (3)0.017 (2)−0.0057 (19)−0.0003 (18)0.0014 (18)
C40.019 (2)0.019 (3)0.013 (2)−0.0018 (19)0.0021 (17)0.0032 (18)
C50.010 (2)0.017 (3)0.019 (2)−0.0036 (18)0.0036 (17)0.0028 (18)
C60.0098 (19)0.015 (2)0.019 (2)−0.0030 (17)0.0002 (17)0.0018 (18)
C70.026 (3)0.028 (3)0.022 (2)−0.010 (2)0.000 (2)0.006 (2)
C80.0078 (19)0.013 (2)0.019 (2)−0.0016 (17)0.0057 (16)0.0034 (18)
C90.014 (2)0.024 (3)0.023 (2)−0.009 (2)−0.0042 (18)0.003 (2)
C100.0089 (19)0.021 (3)0.020 (2)−0.0030 (18)0.0020 (17)−0.0019 (19)
C110.0093 (19)0.024 (3)0.018 (2)−0.0017 (19)0.0008 (17)−0.0018 (19)
C120.014 (2)0.022 (3)0.014 (2)−0.0057 (19)−0.0026 (17)0.0037 (18)
C130.031 (3)0.022 (3)0.021 (2)−0.007 (2)−0.007 (2)0.003 (2)
C140.011 (2)0.024 (3)0.015 (2)−0.0040 (19)−0.0031 (17)0.0025 (18)
C150.018 (2)0.024 (3)0.020 (2)−0.006 (2)−0.0002 (18)−0.0007 (19)
C160.027 (3)0.018 (3)0.035 (3)−0.004 (2)−0.007 (2)0.000 (2)
C170.021 (2)0.030 (3)0.028 (3)−0.001 (2)−0.002 (2)−0.010 (2)
C180.012 (2)0.039 (3)0.019 (2)−0.006 (2)0.0002 (18)−0.005 (2)
C190.015 (2)0.028 (3)0.016 (2)−0.008 (2)−0.0007 (17)0.0033 (19)
C200.029 (3)0.027 (3)0.039 (3)−0.002 (2)−0.009 (2)0.000 (2)
C210.031 (3)0.058 (4)0.031 (3)−0.010 (3)−0.001 (2)0.005 (3)
C220.048 (4)0.035 (4)0.036 (3)−0.004 (3)−0.003 (3)−0.009 (3)
C230.020 (3)0.036 (3)0.043 (3)0.002 (2)−0.009 (2)−0.005 (3)

Geometric parameters (Å, °)

Zn1—O12.043 (3)C7—H7B0.9800
Zn1—O1i2.029 (3)C7—H7C0.9800
Zn1—O22.031 (3)C8—C91.506 (6)
Zn1—O1w1.993 (3)C9—H9A0.9800
Zn1—N12.077 (4)C9—H9B0.9800
Zn1—Zn1i3.1485 (9)C9—H9C0.9800
S2—O41.503 (3)C10—C111.518 (5)
S2—C221.775 (6)C11—C121.502 (6)
S2—C231.786 (5)C11—H11A0.9900
S1—O31.509 (3)C11—H11B0.9900
S1—C211.771 (5)C12—C131.365 (6)
S1—C201.776 (5)C12—C141.428 (6)
O1—C11.335 (5)C13—H130.9500
O1—Zn1i2.029 (3)C14—C151.406 (6)
O2—C101.277 (5)C14—C191.408 (6)
O1W—H1W10.8400C15—C161.374 (7)
O1W—H1W20.8400C15—H150.9500
N1—C81.297 (5)C16—C171.408 (7)
N1—N21.410 (4)C16—H160.9500
N2—C101.328 (6)C17—C181.368 (7)
N3—C131.363 (6)C17—H170.9500
N3—C191.374 (6)C18—C191.404 (7)
N3—H3N0.8800C18—H180.9500
C1—C21.404 (6)C20—H20A0.9800
C1—C61.420 (6)C20—H20B0.9800
C2—C31.377 (6)C20—H20C0.9800
C2—H20.9500C21—H21A0.9800
C3—C41.401 (6)C21—H21B0.9800
C3—H30.9500C21—H21C0.9800
C4—C51.375 (6)C22—H22A0.9800
C4—C71.515 (6)C22—H22B0.9800
C5—C61.408 (6)C22—H22C0.9800
C5—H50.9500C23—H23A0.9800
C6—C81.472 (5)C23—H23B0.9800
C7—H7A0.9800C23—H23C0.9800
O1—Zn1—O1i78.7 (1)C8—C9—H9B109.5
O1—Zn1—O2158.8 (1)H9A—C9—H9B109.5
O1—Zn1—O1w105.3 (1)C8—C9—H9C109.5
O1—Zn1—N186.3 (1)H9A—C9—H9C109.5
O1i—Zn1—O2106.0 (1)H9B—C9—H9C109.5
O1i—Zn1—O1w99.5 (1)O2—C10—N2126.0 (4)
O1i—Zn1—N1146.5 (1)O2—C10—C11118.0 (4)
O2—Zn1—O1w94.5 (1)N2—C10—C11116.0 (4)
O2—Zn1—N178.7 (1)C12—C11—C10111.6 (3)
O1W—Zn1—N1113.4 (1)C12—C11—H11A109.3
O1W—Zn1—Zn1i106.07 (8)C10—C11—H11A109.3
O1i—Zn1—Zn1i39.51 (8)C12—C11—H11B109.3
O2—Zn1—Zn1i141.51 (9)C10—C11—H11B109.3
O1—Zn1—Zn1i39.19 (8)H11A—C11—H11B108.0
N1—Zn1—Zn1i119.67 (10)C13—C12—C14106.0 (4)
O4—S2—C22107.0 (2)C13—C12—C11126.2 (4)
O4—S2—C23106.1 (2)C14—C12—C11127.4 (4)
C22—S2—C2397.8 (3)N3—C13—C12110.7 (5)
O3—S1—C21104.4 (2)N3—C13—H13124.7
O3—S1—C20105.1 (2)C12—C13—H13124.7
C21—S1—C2099.1 (3)C15—C14—C19118.5 (4)
C1—O1—Zn1i129.8 (2)C15—C14—C12134.2 (4)
C1—O1—Zn1128.3 (2)C19—C14—C12107.2 (4)
Zn1i—O1—Zn1101.30 (12)C16—C15—C14119.1 (4)
C10—O2—Zn1111.6 (3)C16—C15—H15120.4
Zn1—O1W—H1W1109.5C14—C15—H15120.4
Zn1—O1W—H1W2109.5C15—C16—C17121.1 (5)
H1W1—O1W—H1W2109.5C15—C16—H16119.4
C8—N1—N2116.0 (4)C17—C16—H16119.4
C8—N1—Zn1131.5 (3)C18—C17—C16121.5 (5)
N2—N1—Zn1112.4 (3)C18—C17—H17119.2
C10—N2—N1111.2 (3)C16—C17—H17119.2
C13—N3—C19108.6 (4)C17—C18—C19117.2 (4)
C13—N3—H3N125.7C17—C18—H18121.4
C19—N3—H3N125.7C19—C18—H18121.4
O1—C1—C2118.6 (4)N3—C19—C18130.0 (4)
O1—C1—C6122.8 (4)N3—C19—C14107.5 (4)
C2—C1—C6118.6 (4)C18—C19—C14122.5 (5)
C3—C2—C1122.1 (4)S1—C20—H20A109.5
C3—C2—H2118.9S1—C20—H20B109.5
C1—C2—H2118.9H20A—C20—H20B109.5
C2—C3—C4120.4 (4)S1—C20—H20C109.5
C2—C3—H3119.8H20A—C20—H20C109.5
C4—C3—H3119.8H20B—C20—H20C109.5
C5—C4—C3117.2 (4)S1—C21—H21A109.5
C5—C4—C7121.9 (4)S1—C21—H21B109.5
C3—C4—C7120.9 (4)H21A—C21—H21B109.5
C4—C5—C6124.7 (4)S1—C21—H21C109.5
C4—C5—H5117.7H21A—C21—H21C109.5
C6—C5—H5117.7H21B—C21—H21C109.5
C5—C6—C1116.8 (4)S2—C22—H22A109.5
C5—C6—C8117.3 (4)S2—C22—H22B109.5
C1—C6—C8125.8 (4)H22A—C22—H22B109.5
C4—C7—H7A109.5S2—C22—H22C109.5
C4—C7—H7B109.5H22A—C22—H22C109.5
H7A—C7—H7B109.5H22B—C22—H22C109.5
C4—C7—H7C109.5S2—C23—H23A109.5
H7A—C7—H7C109.5S2—C23—H23B109.5
H7B—C7—H7C109.5H23A—C23—H23B109.5
N1—C8—C6120.3 (4)S2—C23—H23C109.5
N1—C8—C9121.1 (4)H23A—C23—H23C109.5
C6—C8—C9118.6 (4)H23B—C23—H23C109.5
C8—C9—H9A109.5
O1W—Zn1—O1—C191.0 (4)C2—C1—C6—C52.7 (6)
O1i—Zn1—O1—C1−172.2 (4)O1—C1—C6—C84.2 (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—C66.6 (6)
O1W—Zn1—O1—Zn1i−96.87 (14)N2—N1—C8—C91.6 (6)
O1i—Zn1—O1—Zn1i0.0Zn1—N1—C8—C9−173.6 (3)
O2—Zn1—O1—Zn1i105.2 (3)C5—C6—C8—N1164.2 (4)
N1—Zn1—O1—Zn1i149.86 (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—C10147.8 (3)C1—C6—C8—C9162.7 (4)
O1—Zn1—O2—C1047.6 (5)Zn1—O2—C10—N2−2.8 (6)
N1—Zn1—O2—C102.0 (3)Zn1—O2—C10—C11176.2 (3)
Zn1i—Zn1—O2—C10126.0 (3)N1—N2—C10—O21.7 (6)
O1W—Zn1—N1—C8−95.9 (4)N1—N2—C10—C11−177.3 (3)
O1i—Zn1—N1—C872.1 (5)O2—C10—C11—C1245.9 (6)
O2—Zn1—N1—C8174.1 (4)N2—C10—C11—C12−135.0 (4)
O1—Zn1—N1—C89.1 (4)C10—C11—C12—C13−72.6 (6)
Zn1i—Zn1—N1—C830.5 (4)C10—C11—C12—C1499.6 (5)
O1W—Zn1—N1—N288.7 (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—N3173.2 (4)
O1—Zn1—N1—N2−166.2 (3)C13—C12—C14—C15178.4 (5)
Zn1i—Zn1—N1—N2−144.8 (2)C11—C12—C14—C154.9 (7)
C8—N1—N2—C10−175.8 (4)C13—C12—C14—C191.2 (4)
Zn1—N1—N2—C100.3 (4)C11—C12—C14—C19−172.3 (4)
Zn1i—O1—C1—C229.5 (6)C19—C14—C15—C161.5 (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—C619.7 (6)C15—C16—C17—C18−0.7 (7)
O1—C1—C2—C3178.2 (4)C16—C17—C18—C190.5 (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—C141.4 (5)
C2—C3—C4—C52.8 (7)C17—C18—C19—N3177.6 (4)
C2—C3—C4—C7−179.0 (4)C17—C18—C19—C140.7 (6)
C3—C4—C5—C6−2.0 (7)C15—C14—C19—N3−179.3 (4)
C7—C4—C5—C6179.8 (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—C8177.7 (4)C12—C14—C19—C18175.9 (4)
O1—C1—C6—C5−177.5 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O30.841.802.608 (4)161
O1W—H1W2···N2ii0.841.872.703 (4)173
N3—H3N···O40.881.952.822 (5)172

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

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

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