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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1593.
Published online 2009 June 17. doi:  10.1107/S1600536809021023
PMCID: PMC2969371

N-Phenyl-4-(8-phenyl-4,5-dihydro-1,2-benzoxazolo[4,5-d]thia­zol-2-yl)piperidine-1-carboxamide

Abstract

In the title molecule, C26H24N4O2S, the dihedral angle between the isoxazole ring and the adjoining benzene ring is 21.4 (5)°, and between the isoxazole ring and the thia­zole ring is 14.3 (4)°. The piperidine ring is in a chair conformation. In the crystal structure, mol­ecules are linked by inter­molecular N—H(...)O and weak C—H(...)O hydrogen bonds into one-dimensional chains along [001].

Related literature

The title compound is a potential D1 protease inhibitor. D1 protease is a potential herbicidal target, see: Duff et al. (2007 [triangle]). For synthetic details, see: Bond et al. (2003 [triangle]); Hu et al. (2009 [triangle]).

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Object name is e-65-o1593-scheme1.jpg

Experimental

Crystal data

  • C26H24N4O2S
  • M r = 456.55
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1593-efi1.jpg
  • a = 22.2844 (6) Å
  • b = 10.1911 (3) Å
  • c = 10.2842 (3) Å
  • β = 102.282 (2)°
  • V = 2282.11 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 298 K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.966, T max = 0.983
  • 16337 measured reflections
  • 4477 independent reflections
  • 3399 reflections with I > 2σ(I)
  • R int = 0.093

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.143
  • S = 1.04
  • 4477 reflections
  • 301 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021023/lh2833sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021023/lh2833Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20672043, 20672044).

supplementary crystallographic information

Comment

We are interested in the title compound as a potential D1 protease inhibitor. D1 protease is a potential herbicidal target (Duff et al. 2007). To find the possible D1 inhibitors, virtual screening was performed and a molecule containing isoxazole, thiazole and piperidine rings was designed and synthesized (Hu et al. 2009).

The title moleclue (Fig. 1) contains isoxazole, thiazole, piperdine and two benzene rings. The dihedral angle between the the isoxazole ring and the adjoining benzene ring is 21.4 (5)° and the dihedral angle between the isoxazole and the thiazole rings is 14.3 (4)°. The piperidine ring is in a chair conformation. In the crystal structure, molecules are linked by intermolecular N-H···O and weak C-H···O hydrogen bonds into one-dimensional chains along [001] (see Fig. 2).

Experimental

3-phenyl-6,7-dihydrobenzo[d]isoxazole-4(5H)-one was synthesized by a literature method (Bond et al., 2003). This intermediate (1 mmol) was treated with NBS (2.5 mmol) and NH4OAc (0.1 mmol) in dry ether to obtain the monobromo ketone and a trace amounts of polybromonated derivatives. The target product was formed by a published procedure (Hu et al., 2009). Slow diffusion of hexane into a ethyl acetate solution of the title compound gave single crystals suitable for X-ray analysis.

Refinement

All H atoms bonded to C atoms were placed in geometrically idealized positions and included in a riding-model approximation with C—H = 0.93 Å (aromatic), 0.97Å (methylene) and 0.98Å (methine), with Uiso(H) = 1.2Ueq(C). The H atom bonded to N4 was found in a difference Fourier map and refined with the restraint of N—H = 0.86 (2)Å and Uiso(H) = 1.2Ueq(N).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 10% probability level.
Fig. 2.
Part of the crystal structure of the title compound with hydrogen bonds drawn as dashed lines. Only H atom involved in hydrogen bonds have been shown.

Crystal data

C26H24N4O2SF(000) = 960
Mr = 456.55Dx = 1.329 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4151 reflections
a = 22.2844 (6) Åθ = 2.4–24.8°
b = 10.1911 (3) ŵ = 0.17 mm1
c = 10.2842 (3) ÅT = 298 K
β = 102.282 (2)°Block, colorless
V = 2282.11 (11) Å30.20 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer4477 independent reflections
Radiation source: fine-focus sealed tube3399 reflections with I > 2σ(I)
graphiteRint = 0.093
[var phi] and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −22→27
Tmin = 0.966, Tmax = 0.983k = −12→12
16337 measured reflectionsl = −12→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0715P)2 + 0.1065P] where P = (Fo2 + 2Fc2)/3
4477 reflections(Δ/σ)max = 0.001
301 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = −0.31 e Å3

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*/Ueq
C10.38381 (9)−0.2002 (2)0.3431 (2)0.0421 (5)
C20.34151 (12)−0.2361 (2)0.4168 (3)0.0602 (7)
H20.3287−0.17500.47230.072*
C30.31805 (13)−0.3619 (3)0.4091 (3)0.0733 (8)
H30.2894−0.38460.45920.088*
C40.33650 (12)−0.4538 (2)0.3283 (3)0.0663 (7)
H40.3203−0.53820.32270.080*
C50.37882 (15)−0.4196 (3)0.2565 (3)0.0717 (8)
H50.3920−0.48190.20270.086*
C60.40231 (12)−0.2945 (2)0.2623 (2)0.0605 (7)
H60.4309−0.27280.21170.073*
C70.41255 (9)−0.0693 (2)0.35423 (19)0.0398 (5)
C80.39483 (9)0.05256 (19)0.40386 (19)0.0384 (5)
C90.44192 (9)0.1341 (2)0.4002 (2)0.0424 (5)
C100.44851 (11)0.2734 (2)0.4429 (2)0.0520 (6)
H10A0.43260.33030.36790.062*
H10B0.49150.29410.47590.062*
C110.41283 (11)0.2956 (2)0.5528 (2)0.0528 (6)
H11A0.43760.26710.63740.063*
H11B0.40460.38850.55950.063*
C120.35307 (10)0.2212 (2)0.5246 (2)0.0453 (5)
C130.34382 (9)0.10585 (19)0.45761 (19)0.0388 (5)
C140.25309 (10)0.1164 (2)0.5099 (2)0.0449 (5)
C150.18845 (10)0.0794 (2)0.5137 (2)0.0475 (5)
H150.1860−0.01660.51040.057*
C160.14331 (10)0.1320 (2)0.3913 (2)0.0491 (6)
H16A0.14630.22690.38930.059*
H16B0.15430.09790.31140.059*
C170.07811 (10)0.0935 (3)0.3925 (2)0.0556 (6)
H17A0.05050.13170.31610.067*
H17B0.0740−0.00120.38630.067*
C180.10164 (10)0.0865 (3)0.6342 (2)0.0595 (7)
H18A0.0978−0.00830.63470.071*
H18B0.08910.12040.71250.071*
C190.16795 (10)0.1235 (3)0.6394 (2)0.0553 (6)
H19A0.19400.08300.71650.066*
H19B0.17250.21790.64870.066*
C200.01279 (9)0.2148 (2)0.5258 (2)0.0433 (5)
C21−0.07915 (10)0.3251 (2)0.4003 (2)0.0431 (5)
C22−0.12464 (11)0.2917 (2)0.2914 (2)0.0561 (6)
H22−0.11580.23430.22770.067*
C23−0.18266 (12)0.3426 (3)0.2767 (3)0.0740 (8)
H23−0.21280.31890.20310.089*
C24−0.19687 (15)0.4266 (3)0.3673 (4)0.0837 (10)
H24−0.23660.45870.35770.100*
C25−0.15178 (17)0.4637 (3)0.4735 (3)0.0849 (10)
H25−0.16100.52280.53530.102*
C26−0.09237 (13)0.4143 (3)0.4903 (2)0.0650 (7)
H26−0.06190.44140.56170.078*
N10.46608 (8)−0.05766 (18)0.32118 (18)0.0496 (5)
N20.28756 (7)0.04708 (17)0.44870 (17)0.0424 (4)
N30.06154 (8)0.1393 (2)0.51501 (17)0.0559 (5)
N4−0.02020 (9)0.2682 (2)0.41087 (17)0.0505 (5)
H4A−0.0118 (11)0.252 (2)0.3352 (14)0.061*
O10.48560 (7)0.07301 (15)0.35047 (15)0.0512 (4)
O2−0.00073 (7)0.23519 (17)0.63341 (15)0.0570 (5)
S10.28825 (3)0.25928 (6)0.58254 (6)0.0556 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0326 (11)0.0463 (12)0.0465 (12)0.0101 (9)0.0064 (9)−0.0035 (9)
C20.0577 (15)0.0463 (14)0.0844 (18)0.0019 (11)0.0329 (14)−0.0132 (12)
C30.0666 (18)0.0546 (16)0.107 (2)−0.0024 (13)0.0374 (16)0.0010 (15)
C40.0605 (17)0.0456 (14)0.0858 (19)0.0021 (12)0.0000 (15)−0.0082 (13)
C50.092 (2)0.0520 (16)0.0706 (18)0.0115 (14)0.0173 (16)−0.0169 (13)
C60.0689 (17)0.0553 (15)0.0634 (15)0.0096 (13)0.0281 (13)−0.0095 (12)
C70.0318 (11)0.0474 (12)0.0407 (11)0.0080 (9)0.0086 (9)0.0010 (9)
C80.0329 (11)0.0428 (11)0.0398 (11)0.0057 (9)0.0088 (9)0.0019 (9)
C90.0374 (12)0.0468 (12)0.0440 (12)0.0053 (10)0.0113 (9)0.0051 (9)
C100.0477 (14)0.0475 (13)0.0621 (14)−0.0023 (10)0.0145 (11)0.0070 (11)
C110.0540 (14)0.0445 (12)0.0585 (14)−0.0030 (11)0.0088 (11)−0.0057 (10)
C120.0455 (13)0.0439 (12)0.0486 (12)0.0052 (10)0.0144 (10)−0.0007 (10)
C130.0333 (11)0.0432 (11)0.0400 (11)0.0062 (9)0.0082 (9)−0.0002 (9)
C140.0421 (12)0.0473 (12)0.0479 (12)0.0091 (10)0.0154 (10)0.0005 (10)
C150.0400 (12)0.0503 (13)0.0560 (14)0.0094 (10)0.0192 (10)0.0031 (10)
C160.0498 (13)0.0598 (14)0.0421 (12)0.0112 (11)0.0199 (10)−0.0044 (10)
C170.0438 (13)0.0783 (17)0.0466 (13)0.0153 (12)0.0141 (10)−0.0049 (12)
C180.0449 (14)0.0878 (19)0.0496 (14)0.0157 (12)0.0185 (11)0.0167 (12)
C190.0448 (13)0.0787 (17)0.0440 (13)0.0149 (12)0.0135 (10)0.0100 (11)
C200.0312 (11)0.0647 (14)0.0365 (11)−0.0034 (10)0.0129 (9)0.0008 (10)
C210.0422 (12)0.0505 (13)0.0413 (12)0.0065 (10)0.0194 (10)0.0049 (9)
C220.0505 (14)0.0544 (14)0.0616 (15)0.0082 (11)0.0077 (12)0.0006 (11)
C230.0472 (16)0.0771 (19)0.093 (2)0.0052 (14)0.0049 (14)0.0210 (17)
C240.0659 (19)0.106 (2)0.090 (2)0.0389 (18)0.0401 (18)0.040 (2)
C250.111 (3)0.084 (2)0.073 (2)0.0495 (19)0.051 (2)0.0113 (16)
C260.0785 (19)0.0678 (16)0.0510 (15)0.0202 (14)0.0193 (13)−0.0004 (12)
N10.0399 (11)0.0538 (12)0.0583 (12)0.0072 (8)0.0179 (9)−0.0006 (9)
N20.0348 (10)0.0452 (10)0.0495 (10)0.0071 (8)0.0137 (8)−0.0033 (8)
N30.0403 (11)0.0930 (15)0.0373 (10)0.0200 (10)0.0149 (8)0.0040 (10)
N40.0423 (11)0.0793 (14)0.0336 (10)0.0132 (9)0.0160 (8)−0.0005 (9)
O10.0378 (8)0.0556 (10)0.0638 (10)0.0034 (7)0.0193 (7)0.0046 (7)
O20.0468 (9)0.0918 (13)0.0377 (8)0.0095 (8)0.0210 (7)0.0037 (8)
S10.0570 (4)0.0477 (4)0.0684 (4)0.0070 (3)0.0272 (3)−0.0110 (3)

Geometric parameters (Å, °)

C1—C21.379 (3)C15—C161.531 (3)
C1—C61.389 (3)C15—H150.9800
C1—C71.474 (3)C16—C171.508 (3)
C2—C31.380 (3)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.371 (4)C17—N31.463 (3)
C3—H30.9300C17—H17A0.9700
C4—C51.361 (4)C17—H17B0.9700
C4—H40.9300C18—N31.458 (3)
C5—C61.375 (4)C18—C191.515 (3)
C5—H50.9300C18—H18A0.9700
C6—H60.9300C18—H18B0.9700
C7—N11.313 (2)C19—H19A0.9700
C7—C81.430 (3)C19—H19B0.9700
C8—C91.346 (3)C20—O21.225 (2)
C8—C131.470 (3)C20—N31.355 (3)
C9—O11.345 (2)C20—N41.365 (3)
C9—C101.484 (3)C21—C261.373 (3)
C10—C111.531 (3)C21—C221.384 (3)
C10—H10A0.9700C21—N41.419 (3)
C10—H10B0.9700C22—C231.371 (4)
C11—C121.506 (3)C22—H220.9300
C11—H11A0.9700C23—C241.352 (4)
C11—H11B0.9700C23—H230.9300
C12—C131.356 (3)C24—C251.370 (5)
C12—S11.720 (2)C24—H240.9300
C13—N21.375 (3)C25—C261.393 (4)
C14—N21.301 (3)C25—H250.9300
C14—C151.498 (3)C26—H260.9300
C14—S11.744 (2)N1—O11.413 (2)
C15—C191.527 (3)N4—H4A0.854 (10)
C2—C1—C6118.0 (2)C17—C16—H16A109.3
C2—C1—C7122.26 (19)C15—C16—H16A109.3
C6—C1—C7119.6 (2)C17—C16—H16B109.3
C1—C2—C3120.6 (2)C15—C16—H16B109.3
C1—C2—H2119.7H16A—C16—H16B108.0
C3—C2—H2119.7N3—C17—C16110.11 (19)
C4—C3—C2120.7 (3)N3—C17—H17A109.6
C4—C3—H3119.7C16—C17—H17A109.6
C2—C3—H3119.7N3—C17—H17B109.6
C5—C4—C3119.1 (2)C16—C17—H17B109.6
C5—C4—H4120.5H17A—C17—H17B108.2
C3—C4—H4120.5N3—C18—C19110.86 (19)
C4—C5—C6121.0 (2)N3—C18—H18A109.5
C4—C5—H5119.5C19—C18—H18A109.5
C6—C5—H5119.5N3—C18—H18B109.5
C5—C6—C1120.6 (3)C19—C18—H18B109.5
C5—C6—H6119.7H18A—C18—H18B108.1
C1—C6—H6119.7C18—C19—C15111.3 (2)
N1—C7—C8110.43 (19)C18—C19—H19A109.4
N1—C7—C1117.71 (18)C15—C19—H19A109.4
C8—C7—C1131.73 (19)C18—C19—H19B109.4
C9—C8—C7104.49 (18)C15—C19—H19B109.4
C9—C8—C13116.91 (19)H19A—C19—H19B108.0
C7—C8—C13138.57 (19)O2—C20—N3121.71 (19)
O1—C9—C8110.89 (18)O2—C20—N4121.6 (2)
O1—C9—C10121.44 (18)N3—C20—N4116.71 (18)
C8—C9—C10127.67 (19)C26—C21—C22118.9 (2)
C9—C10—C11109.03 (18)C26—C21—N4123.1 (2)
C9—C10—H10A109.9C22—C21—N4117.95 (19)
C11—C10—H10A109.9C23—C22—C21120.5 (3)
C9—C10—H10B109.9C23—C22—H22119.7
C11—C10—H10B109.9C21—C22—H22119.7
H10A—C10—H10B108.3C24—C23—C22121.1 (3)
C12—C11—C10111.11 (18)C24—C23—H23119.4
C12—C11—H11A109.4C22—C23—H23119.4
C10—C11—H11A109.4C23—C24—C25119.0 (3)
C12—C11—H11B109.4C23—C24—H24120.5
C10—C11—H11B109.4C25—C24—H24120.5
H11A—C11—H11B108.0C24—C25—C26121.0 (3)
C13—C12—C11124.5 (2)C24—C25—H25119.5
C13—C12—S1108.90 (17)C26—C25—H25119.5
C11—C12—S1126.36 (16)C21—C26—C25119.4 (3)
C12—C13—N2116.70 (18)C21—C26—H26120.3
C12—C13—C8117.74 (19)C25—C26—H26120.3
N2—C13—C8125.54 (18)C7—N1—O1106.56 (16)
N2—C14—C15123.1 (2)C14—N2—C13110.80 (18)
N2—C14—S1113.77 (16)C20—N3—C18119.97 (18)
C15—C14—S1123.14 (16)C20—N3—C17127.24 (18)
C14—C15—C19114.20 (19)C18—N3—C17112.65 (18)
C14—C15—C16110.96 (18)C20—N4—C21123.28 (18)
C19—C15—C16109.26 (17)C20—N4—H4A122.1 (17)
C14—C15—H15107.4C21—N4—H4A112.7 (17)
C19—C15—H15107.4C9—O1—N1107.61 (15)
C16—C15—H15107.4C12—S1—C1489.84 (10)
C17—C16—C15111.60 (19)
C6—C1—C2—C3−0.6 (4)C19—C15—C16—C17−54.2 (3)
C7—C1—C2—C3−176.5 (2)C15—C16—C17—N356.6 (3)
C1—C2—C3—C40.2 (4)N3—C18—C19—C15−55.6 (3)
C2—C3—C4—C50.6 (4)C14—C15—C19—C18178.19 (19)
C3—C4—C5—C6−1.1 (4)C16—C15—C19—C1853.3 (3)
C4—C5—C6—C10.7 (4)C26—C21—C22—C23−2.8 (4)
C2—C1—C6—C50.1 (4)N4—C21—C22—C23179.3 (2)
C7—C1—C6—C5176.1 (2)C21—C22—C23—C240.3 (4)
C2—C1—C7—N1155.8 (2)C22—C23—C24—C251.8 (4)
C6—C1—C7—N1−20.0 (3)C23—C24—C25—C26−1.3 (5)
C2—C1—C7—C8−19.6 (3)C22—C21—C26—C253.2 (4)
C6—C1—C7—C8164.5 (2)N4—C21—C26—C25−179.0 (2)
N1—C7—C8—C9−1.3 (2)C24—C25—C26—C21−1.2 (4)
C1—C7—C8—C9174.4 (2)C8—C7—N1—O10.9 (2)
N1—C7—C8—C13−178.7 (2)C1—C7—N1—O1−175.46 (16)
C1—C7—C8—C13−3.1 (4)C15—C14—N2—C13178.04 (19)
C7—C8—C9—O11.2 (2)S1—C14—N2—C130.0 (2)
C13—C8—C9—O1179.31 (16)C12—C13—N2—C14−0.5 (3)
C7—C8—C9—C10−178.8 (2)C8—C13—N2—C14177.82 (19)
C13—C8—C9—C10−0.7 (3)O2—C20—N3—C18−3.7 (3)
O1—C9—C10—C11−151.80 (19)N4—C20—N3—C18175.6 (2)
C8—C9—C10—C1128.2 (3)O2—C20—N3—C17171.6 (2)
C9—C10—C11—C12−39.1 (2)N4—C20—N3—C17−9.1 (4)
C10—C11—C12—C1330.6 (3)C19—C18—N3—C20−125.6 (2)
C10—C11—C12—S1−155.19 (17)C19—C18—N3—C1758.5 (3)
C11—C12—C13—N2175.8 (2)C16—C17—N3—C20125.6 (2)
S1—C12—C13—N20.7 (2)C16—C17—N3—C18−58.8 (3)
C11—C12—C13—C8−2.7 (3)O2—C20—N4—C21−14.7 (3)
S1—C12—C13—C8−177.74 (15)N3—C20—N4—C21166.0 (2)
C9—C8—C13—C12−13.7 (3)C26—C21—N4—C2048.3 (3)
C7—C8—C13—C12163.5 (2)C22—C21—N4—C20−133.9 (2)
C9—C8—C13—N2168.03 (19)C8—C9—O1—N1−0.7 (2)
C7—C8—C13—N2−14.8 (4)C10—C9—O1—N1179.28 (18)
N2—C14—C15—C19149.7 (2)C7—N1—O1—C9−0.1 (2)
S1—C14—C15—C19−32.5 (3)C13—C12—S1—C14−0.54 (16)
N2—C14—C15—C16−86.3 (3)C11—C12—S1—C14−175.5 (2)
S1—C14—C15—C1691.5 (2)N2—C14—S1—C120.30 (17)
C14—C15—C16—C17179.03 (18)C15—C14—S1—C12−177.70 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C17—H17A···O2i0.972.403.353 (3)167
N4—H4A···O2i0.85 (1)2.15 (1)2.976 (2)164 (2)

Symmetry codes: (i) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2833).

References

  • Bond, J. W., Hachisu, Y., Matsuura, T. & Suzuk, K. (2003). Org. Lett.5, 319–394.
  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Duff, S. M. G., Chen, Y.-C. S., Fabbri, B. J., Yalamanchili, G., Hamper, B. C., Walker, D. M., Brookfiled, F. A., Boyd, E. A., Ashton, M. R., Yarnold, C. J. & Cajacob, C. A. (2007). Pestic. Biochem. Physiol.88, 1–3.
  • Hu, D.-J., Liu, S.-F., Huang, T.-H., Tu, H.-Y. & Zhang, A.-D. (2009). Molecules, 14, 1288–1303. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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