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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3278.
Published online 2010 November 24. doi:  10.1107/S160053681004804X
PMCID: PMC3011443

Diniconazole

Abstract

The asymmetric unit of the title compound [systematic name: (E)-1-(2,4-dichloro­phen­yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol], C15H17Cl2N3O, contains two mol­ecules in which the dihedral angles between the triazole and benzene rings are 9.4 (2) and 35.0 (2)°. In the crystal, the mol­ecules are linked by O—H(...)N hydrogen bonds, forming C(7) chains propagating in [010].

Related literature

For background to the use of diniconazole as a fungicide, see: Sumitomo Chemical (1984 [triangle]). For further synthetic details, see: Xia et al. (2001 [triangle]).

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Object name is e-66-o3278-scheme1.jpg

Experimental

Crystal data

  • C15H17Cl2N3O
  • M r = 326.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3278-efi1.jpg
  • a = 7.2321 (15) Å
  • b = 20.248 (4) Å
  • c = 22.449 (5) Å
  • β = 96.072 (2)°
  • V = 3268.8 (12) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.40 mm−1
  • T = 296 K
  • 0.22 × 0.18 × 0.07 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.917, T max = 0.973
  • 24930 measured reflections
  • 6074 independent reflections
  • 4232 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.179
  • S = 1.02
  • 6074 reflections
  • 391 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.06 e Å−3
  • Δρmin = −0.53 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004804X/hb5745sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004804X/hb5745Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Foundation of Jiangxi Agricultural University, China (2964).

supplementary crystallographic information

Experimental

The synthesis process of diniconazole is carried out by the three steps of condensing, using a-triazolylpinacolone and 2,4-dichlorobenzaldehyde for material shifting and reduing, using a modified Xia reaction (Xia et al., 2001). Diniconazole was recrystallized from ethanol, and colourless blocks were obtained by slow concentration of a water/ethanol solution. m.p. 134–138 °C (m.p.134–156°C). Anal. Calcd. For C15H17Cl2N3O (%) (Mr = 326.22): C, 55.23; H, 5.25; N, 12.88. Found (%): C, 55.21; H, 5.36; N, 12.90.

Refinement

All H atoms were included in calculated positions and refined as riding atoms, with C—H = 0.93–0.96 Å, O—H = 0.82 Å and N—H = 0.86–0.89 Å, with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms.

Figures

Fig. 1.
The molecular structure of (I), showing displacement ellipsoids at the 40% probability level.
Fig. 2.
The crystal packing of (I), showing hydrogen-bonded chains; H-bonds are shown as dashed lines.

Crystal data

C15H17Cl2N3OF(000) = 1360
Mr = 326.22Dx = 1.326 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6731 reflections
a = 7.2321 (15) Åθ = 2.9–23.7°
b = 20.248 (4) ŵ = 0.40 mm1
c = 22.449 (5) ÅT = 296 K
β = 96.072 (2)°Block, colourless
V = 3268.8 (12) Å30.22 × 0.18 × 0.07 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer6074 independent reflections
Radiation source: fine-focus sealed tube4232 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −8→8
Tmin = 0.917, Tmax = 0.973k = −24→24
24930 measured reflectionsl = −27→27

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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0857P)2 + 2.8116P] where P = (Fo2 + 2Fc2)/3
6074 reflections(Δ/σ)max < 0.001
391 parametersΔρmax = 1.06 e Å3
1 restraintΔρmin = −0.53 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
Cl20.65600 (18)0.67176 (5)0.77688 (5)0.0814 (4)
Cl30.70579 (19)0.44904 (6)1.11219 (5)0.0883 (4)
Cl10.5999 (2)0.83181 (5)0.96433 (4)0.0888 (4)
Cl40.82764 (18)0.21724 (9)1.22070 (6)0.1187 (6)
N40.8131 (4)0.43310 (12)0.90776 (11)0.0446 (6)
C170.7857 (5)0.37039 (19)1.10971 (15)0.0576 (9)
C220.8479 (5)0.34644 (17)1.05758 (14)0.0492 (8)
C190.8393 (5)0.2666 (2)1.15758 (18)0.0713 (12)
C210.9102 (5)0.28044 (19)1.05634 (16)0.0603 (9)
C200.9004 (5)0.2411 (2)1.10768 (19)0.0701 (11)
H200.93650.19701.10720.084*
C180.7834 (5)0.3313 (2)1.16074 (16)0.0705 (11)
H180.74520.34841.19590.085*
O20.7417 (4)0.29529 (11)0.87882 (10)0.0582 (6)
H20.76700.25670.88720.087*
C240.7835 (4)0.38187 (14)0.95063 (13)0.0425 (7)
C250.6605 (5)0.32546 (15)0.92710 (13)0.0459 (7)
H250.66290.29260.95920.055*
N60.8689 (4)0.48664 (14)0.82749 (12)0.0600 (8)
N50.7781 (4)0.49744 (13)0.91967 (12)0.0577 (8)
C300.8680 (5)0.42838 (17)0.85327 (14)0.0536 (8)
H300.90120.38910.83570.064*
C260.4538 (5)0.34365 (17)0.90934 (15)0.0539 (8)
C230.8597 (5)0.39100 (16)1.00591 (14)0.0490 (8)
H230.92830.42961.01320.059*
C310.8128 (6)0.52653 (17)0.87023 (17)0.0631 (10)
H310.79970.57190.86480.076*
C290.4280 (5)0.38712 (18)0.85297 (16)0.0620 (9)
H29A0.49250.36770.82210.093*
H29B0.47740.43040.86230.093*
H29C0.29800.39050.83930.093*
C280.3795 (6)0.3783 (3)0.96174 (19)0.0833 (13)
H28A0.24790.38490.95320.125*
H28B0.43990.42030.96810.125*
H28C0.40370.35170.99710.125*
C270.3483 (6)0.2788 (2)0.8956 (2)0.0816 (13)
H27A0.21840.28800.88580.122*
H27B0.36440.25050.93000.122*
H27C0.39590.25730.86230.122*
O10.4857 (4)1.04993 (11)0.77059 (10)0.0589 (6)
H10.54611.03290.74570.088*
C100.4536 (5)1.00280 (15)0.81480 (14)0.0478 (8)
H100.44440.95970.79480.057*
C90.6143 (4)0.99840 (14)0.86293 (14)0.0440 (7)
C70.6734 (4)0.87704 (15)0.85638 (14)0.0466 (7)
C20.6358 (5)0.82160 (16)0.88971 (14)0.0500 (8)
C80.6993 (5)0.94335 (15)0.88313 (15)0.0484 (8)
H80.78290.94700.91740.058*
C50.6972 (5)0.80365 (17)0.77202 (16)0.0564 (9)
H50.71740.79760.73220.068*
C40.6598 (5)0.75077 (15)0.80720 (16)0.0533 (8)
C30.6285 (5)0.75888 (16)0.86631 (16)0.0549 (8)
H30.60310.72280.88970.066*
C60.7044 (5)0.86592 (16)0.79699 (15)0.0532 (8)
H60.73070.90170.77340.064*
C110.2617 (5)1.01600 (18)0.83808 (16)0.0569 (9)
C140.1120 (6)1.0049 (2)0.7858 (2)0.0780 (12)
H14A0.13231.03450.75370.117*
H14B−0.00821.01320.79870.117*
H14C0.11780.96010.77210.117*
C120.2327 (6)0.9669 (3)0.8877 (2)0.1003 (17)
H12A0.24810.92280.87350.150*
H12B0.10950.97200.89940.150*
H12C0.32220.97520.92160.150*
C130.2417 (6)1.0870 (2)0.8601 (2)0.0906 (15)
H13A0.11641.09410.86910.136*
H13B0.27021.11730.82950.136*
H13C0.32591.09400.89560.136*
N10.6761 (4)1.05896 (12)0.89188 (12)0.0494 (7)
N30.7609 (5)1.16084 (14)0.91014 (16)0.0682 (9)
N20.7569 (6)1.05941 (16)0.94929 (15)0.0791 (10)
C150.6829 (5)1.12015 (16)0.86994 (17)0.0593 (9)
H150.63801.13220.83110.071*
C160.8031 (7)1.1211 (2)0.9574 (2)0.0840 (13)
H160.86141.13670.99360.101*
H211.0000 (13)0.2641 (5)1.0193 (4)−0.050 (2)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl20.1121 (9)0.0410 (5)0.0934 (8)0.0038 (5)0.0210 (6)−0.0089 (5)
Cl30.1113 (9)0.0765 (7)0.0782 (7)0.0223 (6)0.0151 (6)−0.0110 (5)
Cl10.1515 (12)0.0683 (6)0.0495 (5)−0.0040 (7)0.0248 (6)0.0095 (5)
Cl40.0886 (9)0.1778 (15)0.0906 (9)0.0219 (9)0.0131 (7)0.0851 (10)
N40.0555 (16)0.0405 (14)0.0382 (13)−0.0042 (12)0.0067 (12)0.0008 (11)
C170.056 (2)0.069 (2)0.0459 (18)−0.0022 (17)0.0006 (16)−0.0012 (16)
C220.0500 (18)0.059 (2)0.0368 (16)−0.0066 (15)−0.0038 (14)0.0024 (14)
C190.053 (2)0.101 (3)0.058 (2)0.005 (2)−0.0044 (18)0.033 (2)
C210.057 (2)0.062 (2)0.059 (2)0.0051 (17)−0.0058 (17)0.0132 (17)
C200.063 (2)0.072 (3)0.073 (3)0.012 (2)−0.002 (2)0.026 (2)
C180.060 (2)0.110 (4)0.0413 (19)−0.001 (2)0.0067 (17)0.006 (2)
O20.0883 (18)0.0394 (12)0.0486 (13)0.0003 (12)0.0155 (12)−0.0052 (10)
C240.0518 (18)0.0394 (16)0.0367 (15)0.0001 (13)0.0060 (13)0.0019 (12)
C250.064 (2)0.0397 (16)0.0340 (15)−0.0045 (14)0.0038 (14)0.0038 (12)
N60.080 (2)0.0554 (17)0.0465 (16)−0.0132 (15)0.0149 (15)0.0077 (13)
N50.084 (2)0.0400 (15)0.0513 (16)−0.0028 (14)0.0159 (15)0.0001 (12)
C300.069 (2)0.0512 (19)0.0422 (17)−0.0085 (16)0.0126 (16)−0.0022 (14)
C260.058 (2)0.057 (2)0.0450 (18)−0.0062 (16)−0.0011 (16)0.0065 (15)
C230.058 (2)0.0473 (18)0.0416 (17)−0.0051 (15)0.0029 (15)−0.0006 (14)
C310.088 (3)0.0420 (18)0.060 (2)−0.0079 (18)0.014 (2)0.0083 (16)
C290.066 (2)0.059 (2)0.059 (2)0.0001 (18)−0.0065 (18)0.0087 (17)
C280.062 (2)0.124 (4)0.066 (3)0.011 (2)0.014 (2)−0.001 (3)
C270.081 (3)0.083 (3)0.075 (3)−0.035 (2)−0.015 (2)0.022 (2)
O10.0888 (18)0.0460 (13)0.0459 (13)0.0125 (12)0.0254 (12)0.0075 (10)
C100.065 (2)0.0362 (16)0.0441 (17)0.0056 (14)0.0131 (16)0.0008 (13)
C90.0526 (18)0.0358 (15)0.0464 (17)0.0004 (13)0.0187 (15)0.0000 (13)
C70.0503 (18)0.0379 (16)0.0523 (18)0.0058 (14)0.0088 (15)0.0058 (13)
C20.057 (2)0.0462 (18)0.0470 (18)0.0035 (15)0.0052 (15)0.0076 (14)
C80.0511 (19)0.0426 (17)0.0522 (18)−0.0008 (14)0.0092 (15)0.0019 (14)
C50.070 (2)0.0478 (18)0.0539 (19)0.0079 (16)0.0181 (17)0.0012 (15)
C40.058 (2)0.0369 (17)0.065 (2)0.0070 (15)0.0086 (17)0.0001 (15)
C30.064 (2)0.0380 (17)0.063 (2)0.0019 (15)0.0069 (17)0.0126 (15)
C60.066 (2)0.0404 (17)0.0561 (19)0.0059 (15)0.0193 (17)0.0100 (15)
C110.056 (2)0.064 (2)0.0516 (19)0.0035 (17)0.0090 (16)0.0021 (16)
C140.067 (3)0.085 (3)0.080 (3)0.005 (2)−0.003 (2)0.001 (2)
C120.066 (3)0.148 (5)0.090 (3)−0.004 (3)0.025 (2)0.046 (3)
C130.074 (3)0.099 (3)0.102 (3)0.019 (3)0.023 (3)−0.038 (3)
N10.0616 (17)0.0397 (14)0.0490 (15)−0.0004 (12)0.0154 (13)−0.0025 (11)
N30.089 (2)0.0410 (16)0.076 (2)−0.0033 (15)0.0162 (18)−0.0121 (16)
N20.124 (3)0.0556 (19)0.0550 (19)−0.0067 (19)−0.0017 (19)−0.0046 (15)
C150.076 (2)0.0361 (17)0.068 (2)0.0006 (16)0.0168 (19)0.0019 (16)
C160.125 (4)0.055 (2)0.070 (3)−0.005 (2)−0.002 (3)−0.017 (2)

Geometric parameters (Å, °)

Cl2—C41.738 (3)C27—H27B0.9600
Cl3—C171.697 (4)C27—H27C0.9600
Cl1—C21.734 (3)O1—C101.413 (4)
Cl4—C191.743 (4)O1—H10.8200
N4—C301.329 (4)C10—C91.504 (5)
N4—N51.359 (4)C10—C111.557 (5)
N4—C241.446 (4)C10—H100.9800
C17—C221.385 (5)C9—C81.329 (4)
C17—C181.394 (5)C9—N11.437 (4)
C22—C211.411 (5)C7—C21.392 (4)
C22—C231.479 (4)C7—C61.393 (5)
C19—C201.349 (6)C7—C81.475 (4)
C19—C181.375 (6)C2—C31.373 (5)
C21—C201.409 (5)C8—H80.9300
C21—H211.157 (7)C5—C41.374 (5)
C20—H200.9300C5—C61.379 (5)
C18—H180.9300C5—H50.9300
O2—C251.424 (4)C4—C31.379 (5)
O2—H20.8200C3—H30.9300
C24—C231.317 (4)C6—H60.9300
C24—C251.508 (4)C11—C121.524 (5)
C25—C261.550 (5)C11—C141.527 (6)
C25—H250.9800C11—C131.532 (6)
N6—C301.314 (4)C14—H14A0.9600
N6—C311.349 (5)C14—H14B0.9600
N5—C311.304 (4)C14—H14C0.9600
C30—H300.9300C12—H12A0.9600
C26—C281.516 (5)C12—H12B0.9600
C26—C271.534 (5)C12—H12C0.9600
C26—C291.536 (5)C13—H13A0.9600
C23—H230.9300C13—H13B0.9600
C31—H310.9300C13—H13C0.9600
C29—H29A0.9600N1—C151.336 (4)
C29—H29B0.9600N1—N21.358 (4)
C29—H29C0.9600N3—C151.305 (5)
C28—H28A0.9600N3—C161.341 (5)
C28—H28B0.9600N2—C161.302 (5)
C28—H28C0.9600C15—H150.9300
C27—H27A0.9600C16—H160.9300
C30—N4—N5109.3 (3)C10—O1—H1109.5
C30—N4—C24129.9 (3)O1—C10—C9111.9 (3)
N5—N4—C24120.8 (2)O1—C10—C11109.8 (3)
C22—C17—C18121.9 (4)C9—C10—C11114.7 (3)
C22—C17—Cl3119.9 (3)O1—C10—H10106.7
C18—C17—Cl3118.2 (3)C9—C10—H10106.7
C17—C22—C21118.8 (3)C11—C10—H10106.7
C17—C22—C23120.0 (3)C8—C9—N1116.8 (3)
C21—C22—C23121.1 (3)C8—C9—C10126.1 (3)
C20—C19—C18122.1 (4)N1—C9—C10117.0 (3)
C20—C19—Cl4120.2 (4)C2—C7—C6116.4 (3)
C18—C19—Cl4117.7 (3)C2—C7—C8122.6 (3)
C20—C21—C22118.4 (4)C6—C7—C8120.7 (3)
C20—C21—H21120.4 (6)C3—C2—C7122.8 (3)
C22—C21—H21119.3 (6)C3—C2—Cl1118.4 (2)
C19—C20—C21120.8 (4)C7—C2—Cl1118.7 (3)
C19—C20—H20119.6C9—C8—C7126.2 (3)
C21—C20—H20119.6C9—C8—H8116.9
C19—C18—C17118.0 (4)C7—C8—H8116.9
C19—C18—H18121.0C4—C5—C6118.7 (3)
C17—C18—H18121.0C4—C5—H5120.7
C25—O2—H2109.5C6—C5—H5120.7
C23—C24—N4116.7 (3)C5—C4—C3121.5 (3)
C23—C24—C25127.5 (3)C5—C4—Cl2119.2 (3)
N4—C24—C25115.7 (2)C3—C4—Cl2119.3 (3)
O2—C25—C24108.4 (3)C2—C3—C4118.3 (3)
O2—C25—C26111.7 (3)C2—C3—H3120.8
C24—C25—C26115.3 (3)C4—C3—H3120.8
O2—C25—H25107.0C5—C6—C7122.3 (3)
C24—C25—H25107.0C5—C6—H6118.9
C26—C25—H25107.0C7—C6—H6118.9
C30—N6—C31102.0 (3)C12—C11—C14109.0 (4)
C31—N5—N4102.1 (3)C12—C11—C13110.5 (4)
N6—C30—N4110.9 (3)C14—C11—C13107.6 (3)
N6—C30—H30124.5C12—C11—C10109.3 (3)
N4—C30—H30124.5C14—C11—C10107.5 (3)
C28—C26—C27110.1 (3)C13—C11—C10112.8 (3)
C28—C26—C29110.6 (3)C11—C14—H14A109.5
C27—C26—C29108.1 (3)C11—C14—H14B109.5
C28—C26—C25108.7 (3)H14A—C14—H14B109.5
C27—C26—C25107.1 (3)C11—C14—H14C109.5
C29—C26—C25112.2 (3)H14A—C14—H14C109.5
C24—C23—C22126.9 (3)H14B—C14—H14C109.5
C24—C23—H23116.6C11—C12—H12A109.5
C22—C23—H23116.6C11—C12—H12B109.5
N5—C31—N6115.7 (3)H12A—C12—H12B109.5
N5—C31—H31122.1C11—C12—H12C109.5
N6—C31—H31122.1H12A—C12—H12C109.5
C26—C29—H29A109.5H12B—C12—H12C109.5
C26—C29—H29B109.5C11—C13—H13A109.5
H29A—C29—H29B109.5C11—C13—H13B109.5
C26—C29—H29C109.5H13A—C13—H13B109.5
H29A—C29—H29C109.5C11—C13—H13C109.5
H29B—C29—H29C109.5H13A—C13—H13C109.5
C26—C28—H28A109.5H13B—C13—H13C109.5
C26—C28—H28B109.5C15—N1—N2108.3 (3)
H28A—C28—H28B109.5C15—N1—C9130.3 (3)
C26—C28—H28C109.5N2—N1—C9121.1 (3)
H28A—C28—H28C109.5C15—N3—C16102.4 (3)
H28B—C28—H28C109.5C16—N2—N1102.6 (3)
C26—C27—H27A109.5N3—C15—N1111.1 (3)
C26—C27—H27B109.5N3—C15—H15124.4
H27A—C27—H27B109.5N1—C15—H15124.4
C26—C27—H27C109.5N2—C16—N3115.5 (4)
H27A—C27—H27C109.5N2—C16—H16122.2
H27B—C27—H27C109.5N3—C16—H16122.2
C18—C17—C22—C210.2 (5)O1—C10—C9—C8−130.0 (3)
Cl3—C17—C22—C21−178.8 (3)C11—C10—C9—C8104.2 (4)
C18—C17—C22—C23−175.9 (3)O1—C10—C9—N153.3 (3)
Cl3—C17—C22—C235.2 (5)C11—C10—C9—N1−72.6 (3)
C17—C22—C21—C202.1 (5)C6—C7—C2—C3−0.1 (5)
C23—C22—C21—C20178.1 (3)C8—C7—C2—C3−173.9 (3)
C18—C19—C20—C210.3 (6)C6—C7—C2—Cl1178.9 (3)
Cl4—C19—C20—C21179.9 (3)C8—C7—C2—Cl15.2 (5)
C22—C21—C20—C19−2.4 (6)N1—C9—C8—C7−173.0 (3)
C20—C19—C18—C172.0 (6)C10—C9—C8—C710.3 (5)
Cl4—C19—C18—C17−177.6 (3)C2—C7—C8—C9−129.4 (4)
C22—C17—C18—C19−2.2 (6)C6—C7—C8—C957.1 (5)
Cl3—C17—C18—C19176.7 (3)C6—C5—C4—C30.4 (5)
C30—N4—C24—C23131.4 (4)C6—C5—C4—Cl2−178.4 (3)
N5—N4—C24—C23−51.0 (4)C7—C2—C3—C4−0.1 (5)
C30—N4—C24—C25−51.3 (5)Cl1—C2—C3—C4−179.1 (3)
N5—N4—C24—C25126.2 (3)C5—C4—C3—C2−0.1 (5)
C23—C24—C25—O2−123.9 (3)Cl2—C4—C3—C2178.7 (3)
N4—C24—C25—O259.2 (3)C4—C5—C6—C7−0.5 (5)
C23—C24—C25—C26110.0 (4)C2—C7—C6—C50.4 (5)
N4—C24—C25—C26−66.9 (3)C8—C7—C6—C5174.3 (3)
C30—N4—N5—C310.8 (4)O1—C10—C11—C12−177.4 (3)
C24—N4—N5—C31−177.1 (3)C9—C10—C11—C12−50.4 (4)
C31—N6—C30—N40.5 (4)O1—C10—C11—C1464.5 (4)
N5—N4—C30—N6−0.9 (4)C9—C10—C11—C14−168.6 (3)
C24—N4—C30—N6176.8 (3)O1—C10—C11—C13−54.0 (4)
O2—C25—C26—C28−177.3 (3)C9—C10—C11—C1372.9 (4)
C24—C25—C26—C28−53.0 (4)C8—C9—N1—C15148.1 (4)
O2—C25—C26—C2763.7 (3)C10—C9—N1—C15−34.9 (5)
C24—C25—C26—C27−171.9 (3)C8—C9—N1—N2−25.6 (4)
O2—C25—C26—C29−54.7 (4)C10—C9—N1—N2151.4 (3)
C24—C25—C26—C2969.7 (4)C15—N1—N2—C161.0 (5)
N4—C24—C23—C22179.3 (3)C9—N1—N2—C16176.0 (3)
C25—C24—C23—C222.5 (6)C16—N3—C15—N10.7 (4)
C17—C22—C23—C24−125.7 (4)N2—N1—C15—N3−1.1 (4)
C21—C22—C23—C2458.3 (5)C9—N1—C15—N3−175.5 (3)
N4—N5—C31—N6−0.5 (5)N1—N2—C16—N3−0.6 (6)
C30—N6—C31—N50.0 (5)C15—N3—C16—N20.0 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N6i0.822.042.844 (3)165
O2—H2···N3ii0.822.012.812 (4)166

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5745).

References

  • Bruker (1998). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisoconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sumitomo Chemical (1984). Jpn Pestic. Soc.6, 229–236.
  • Xia, H. Y., Duan, Z. X., Tu, Y. M. & Liu, J. H. (2001). Chin. J. Pestic.40, 12–14.

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