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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2928.
Published online 2009 October 31. doi:  10.1107/S1600536809044687
PMCID: PMC2970984

2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl N-ethyl­carbamate

Abstract

The title compound, C13H17NO3, crystallizes with two independent mol­ecules in the asymmetric unit. In the crystal, N—H(...)O hydrogen bonds link the mol­ecules, forming chains propagaiting in [100]. A weak C—H(...)O inter­action also occurs.

Related literature

For background on insecticides related to the title compound, see: Tomlin (1994 [triangle]). For a related structure, see Xu et al. (2005 [triangle]).

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Object name is e-65-o2928-scheme1.jpg

Experimental

Crystal data

  • C13H17NO3
  • M r = 235.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2928-efi1.jpg
  • a = 10.362 (2) Å
  • b = 13.962 (3) Å
  • c = 18.069 (4) Å
  • V = 2614.1 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.26 × 0.20 × 0.08 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.978, T max = 0.993
  • 20967 measured reflections
  • 3256 independent reflections
  • 2338 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.154
  • S = 1.08
  • 3256 reflections
  • 322 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044687/hb5190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044687/hb5190Isup2.hkl

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

Acknowledgments

We would like to thank the Chinese Ministry of Science and Technology (Project Nos. 2005CB221406, 2006BAE02B05) for financial suppport.

supplementary crystallographic information

Comment

The title compound, (I), is an anologue to commercial Carbofuran, which is a popular carbamate insecticide (Tomlin, 1994). Herein, we present its single-crystal structure: it crystallizes with two independent molecules in the asymmetric unit (Figs. 1 & 2), and it has the same space group P212121 like Carbofuran reported previouly (Xu et al., 2005). In the molecule shown in Fig 1, the dihedral angle between the carbamate plane O1/C11/O2/N1 and the benzo ring C5—C10 is 78.50 (5)°, and atom C1 deviates from the C4—C10/O3 plane with an angle of 0.167 (2) Å. In the other molecule, shown in Fig 2, the dihedral angle between the plane O5/O6/C24/N2 and the benzo ring C18—C23 is 79.87 (5)°, and atom C14 lies 0.175 (2)Å out of the plane C17—C23/O4. All these are similar to those reported in the literature (Xu et al., 2005).

In the crystal structure, the two independent molecules in the asymmetric unit are linked by a strong N—H···O hydrogen bond, and each links another adjacent molecule by the N—H···O hydrogen bond. Besides, weak C—H···O H-bonding consolidates the packing (Table 1).

Experimental

The title compound was prepared by reaction of 2,3-dihydro-7-hydroxy-2,2-dimethylbenzofuran with ethylcarbamoyl chloride in 283 K, with a 85% yeild. Colourless prisms of (I) were obtained by evaporation from its ethanoic solution at room temperature.

Refinement

All C-bound H atoms were positioned geometrically and constrained to ride on their parent atoms [C—H distances are 0.93 and 0.97Å with Uiso(H) = 1.2 Ueq(C) for aromatic and CH2 H atoms, 0.96Å with Uiso = 1.5Ueq (C) for CH3 H atoms].

The position and isotropic displacement parameters of the NH H atoms were refined freely. In the absence of significant anomalous dispersion effects, Friedel pairs were merged.

Figures

Fig. 1.
One molecule in the asymmetric unit of (I), showing d isplacement ellipsoids drawn at the 30% probability level.
Fig. 2.
The other molecule in the asymmetric unit of (I), showing displacement ellipsoids drawn at the 30% level.

Crystal data

C13H17NO3F(000) = 1008
Mr = 235.28Dx = 1.196 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5268 reflections
a = 10.362 (2) Åθ = 1.8–27.1°
b = 13.962 (3) ŵ = 0.09 mm1
c = 18.069 (4) ÅT = 293 K
V = 2614.1 (10) Å3Prism, colourless
Z = 80.26 × 0.20 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer3256 independent reflections
Radiation source: rotating anode2338 reflections with I > 2σ(I)
confocalRint = 0.049
Detector resolution: 7.31 pixels mm-1θmax = 27.2°, θmin = 1.8°
ω and [var phi] scansh = −10→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −17→17
Tmin = 0.978, Tmax = 0.993l = −21→23
20967 measured reflections

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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154w = 1/[σ2(Fo2) + (0.083P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3256 reflectionsΔρmax = 0.14 e Å3
322 parametersΔρmin = −0.14 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.029 (3)

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
O10.9284 (3)0.3257 (2)0.01889 (15)0.0801 (8)
O20.9054 (2)0.50324 (18)0.14502 (19)0.0855 (9)
O30.7620 (2)0.38179 (17)0.13896 (15)0.0725 (7)
O40.3318 (3)0.79075 (16)0.11613 (14)0.0758 (7)
O50.2451 (2)0.60024 (16)0.08020 (14)0.0688 (7)
O60.4027 (2)0.51258 (19)0.13447 (16)0.0812 (8)
N10.6932 (3)0.5302 (2)0.12561 (19)0.0709 (8)
N20.1916 (3)0.4821 (2)0.15411 (17)0.0660 (8)
C11.0315 (4)0.2815 (3)−0.0269 (2)0.0762 (10)
C21.1341 (5)0.3563 (3)−0.0360 (3)0.1080 (16)
H2A1.09890.4107−0.06140.162*
H2B1.20440.3303−0.06410.162*
H2C1.16470.37570.01190.162*
C30.9693 (6)0.2508 (4)−0.0979 (3)0.127 (2)
H3A0.90360.2043−0.08750.190*
H3B1.03320.2232−0.12980.190*
H3C0.93120.3054−0.12170.190*
C41.0807 (5)0.1960 (3)0.0181 (2)0.0931 (13)
H4A1.05170.1360−0.00330.112*
H4B1.17430.19580.02050.112*
C51.0226 (4)0.2114 (2)0.0936 (2)0.0729 (10)
C61.0378 (5)0.1657 (3)0.1605 (3)0.0881 (12)
H61.09720.11610.16520.106*
C70.9655 (5)0.1933 (3)0.2198 (3)0.0947 (13)
H70.97660.16260.26500.114*
C80.8759 (4)0.2665 (3)0.2138 (2)0.0840 (12)
H80.82620.28400.25450.101*
C90.8606 (3)0.3134 (2)0.1472 (2)0.0679 (9)
C100.9355 (3)0.2866 (3)0.0874 (2)0.0662 (9)
C110.7964 (3)0.4767 (2)0.13721 (19)0.0612 (8)
C120.6965 (4)0.6335 (3)0.1279 (3)0.0935 (13)
H12A0.64040.65900.08970.112*
H12B0.78360.65540.11790.112*
C130.6545 (7)0.6699 (4)0.2009 (4)0.136 (2)
H13A0.56800.64890.21070.205*
H13B0.65710.73870.20080.205*
H13C0.71110.64590.23860.205*
C140.3854 (4)0.8896 (3)0.1104 (2)0.0773 (10)
C150.4434 (6)0.9120 (5)0.1854 (3)0.1229 (18)
H15A0.37710.90940.22250.184*
H15B0.48060.97490.18450.184*
H15C0.50910.86580.19670.184*
C160.2739 (5)0.9540 (3)0.0911 (4)0.127 (2)
H16A0.23390.93180.04630.190*
H16B0.30471.01820.08400.190*
H16C0.21190.95320.13060.190*
C170.4848 (4)0.8855 (3)0.0467 (2)0.0856 (11)
H17A0.47120.93730.01190.103*
H17B0.57230.88910.06560.103*
C180.4599 (3)0.7908 (2)0.0114 (2)0.0647 (9)
C190.5074 (3)0.7502 (3)−0.0522 (2)0.0731 (10)
H190.56400.7840−0.08240.088*
C200.4699 (4)0.6584 (3)−0.0705 (2)0.0833 (11)
H200.50220.6299−0.11320.100*
C210.3851 (3)0.6086 (3)−0.0262 (2)0.0729 (10)
H210.36030.5469−0.03950.088*
C220.3368 (3)0.6491 (2)0.03737 (19)0.0605 (8)
C230.3733 (3)0.7411 (2)0.05565 (19)0.0584 (8)
C240.2899 (3)0.5289 (2)0.12496 (18)0.0564 (8)
C250.2109 (4)0.4110 (3)0.2117 (2)0.0874 (12)
H25A0.29360.37980.20460.105*
H25B0.14390.36270.20840.105*
C260.2072 (7)0.4562 (6)0.2855 (3)0.166 (3)
H26A0.27460.50310.28900.249*
H26B0.21960.40810.32280.249*
H26C0.12500.48660.29260.249*
H10.622 (4)0.504 (2)0.1267 (18)0.056 (10)*
H20.117 (4)0.503 (3)0.144 (2)0.072 (11)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0670 (16)0.0924 (17)0.0808 (17)0.0327 (14)0.0019 (13)−0.0074 (14)
O20.0409 (12)0.0715 (15)0.144 (2)−0.0031 (11)−0.0087 (15)0.0076 (15)
O30.0450 (12)0.0685 (14)0.1038 (18)0.0029 (11)0.0026 (12)−0.0232 (13)
O40.0812 (16)0.0653 (13)0.0811 (16)−0.0084 (13)0.0173 (13)0.0042 (12)
O50.0460 (11)0.0603 (12)0.1001 (18)0.0058 (10)0.0084 (12)0.0259 (12)
O60.0417 (12)0.0868 (16)0.115 (2)0.0025 (11)−0.0052 (13)0.0285 (16)
N10.0387 (15)0.0758 (19)0.098 (2)0.0029 (14)−0.0018 (15)0.0000 (17)
N20.0449 (15)0.0672 (16)0.086 (2)−0.0045 (14)−0.0054 (14)0.0208 (15)
C10.064 (2)0.084 (2)0.081 (2)0.023 (2)0.0069 (18)−0.012 (2)
C20.091 (3)0.090 (3)0.143 (4)0.013 (3)0.032 (3)−0.007 (3)
C30.122 (4)0.151 (5)0.107 (4)0.045 (4)−0.030 (3)−0.049 (3)
C40.084 (3)0.092 (3)0.104 (3)0.034 (2)0.010 (2)−0.003 (2)
C50.064 (2)0.0597 (18)0.094 (3)0.0074 (17)0.0040 (19)−0.0047 (19)
C60.095 (3)0.062 (2)0.107 (3)0.016 (2)0.003 (3)0.004 (2)
C70.110 (4)0.072 (2)0.102 (3)0.010 (3)0.013 (3)0.008 (2)
C80.095 (3)0.070 (2)0.086 (3)−0.006 (2)0.019 (2)−0.006 (2)
C90.0520 (18)0.0592 (18)0.093 (3)−0.0028 (15)0.0054 (18)−0.0162 (18)
C100.0541 (19)0.0673 (19)0.077 (2)0.0050 (16)−0.0014 (17)−0.0106 (18)
C110.0451 (17)0.0670 (19)0.072 (2)−0.0005 (15)0.0029 (15)−0.0018 (17)
C120.063 (2)0.082 (2)0.135 (4)0.007 (2)0.000 (3)0.029 (3)
C130.147 (5)0.094 (3)0.168 (5)0.004 (4)−0.023 (5)−0.044 (3)
C140.073 (2)0.0630 (19)0.096 (3)−0.0086 (18)0.004 (2)−0.0076 (19)
C150.124 (4)0.136 (4)0.108 (4)−0.031 (4)0.006 (3)−0.024 (3)
C160.091 (3)0.076 (3)0.213 (6)0.008 (3)0.011 (4)0.015 (3)
C170.084 (3)0.077 (2)0.096 (3)−0.021 (2)0.006 (2)0.011 (2)
C180.0516 (18)0.0676 (19)0.075 (2)−0.0058 (16)−0.0013 (16)0.0140 (18)
C190.0522 (19)0.092 (3)0.075 (2)−0.0105 (19)0.0040 (18)0.012 (2)
C200.063 (2)0.102 (3)0.085 (3)−0.004 (2)0.015 (2)−0.012 (2)
C210.058 (2)0.069 (2)0.092 (3)−0.0068 (17)0.0035 (19)−0.002 (2)
C220.0447 (16)0.0575 (17)0.079 (2)0.0017 (14)0.0040 (16)0.0155 (16)
C230.0476 (17)0.0603 (17)0.0673 (19)−0.0004 (14)0.0007 (15)0.0105 (15)
C240.0436 (16)0.0517 (15)0.074 (2)−0.0015 (13)−0.0072 (15)0.0029 (16)
C250.070 (2)0.087 (3)0.106 (3)−0.003 (2)0.000 (2)0.037 (2)
C260.187 (7)0.215 (7)0.096 (4)0.112 (6)0.043 (4)0.060 (4)

Geometric parameters (Å, °)

O1—C101.356 (5)C8—H80.9300
O1—C11.486 (4)C9—C101.381 (5)
O2—C111.198 (4)C12—C131.478 (7)
O3—C111.373 (4)C12—H12A0.9700
O3—C91.406 (4)C12—H12B0.9700
O4—C231.364 (4)C13—H13A0.9600
O4—C141.491 (4)C13—H13B0.9600
O5—C241.365 (4)C13—H13C0.9600
O5—C221.402 (4)C14—C161.506 (6)
O6—C241.203 (4)C14—C151.515 (6)
N1—C111.321 (4)C14—C171.545 (6)
N1—C121.443 (5)C15—H15A0.9600
N1—H10.82 (4)C15—H15B0.9600
N2—C241.320 (4)C15—H15C0.9600
N2—C251.451 (5)C16—H16A0.9600
N2—H20.84 (4)C16—H16B0.9600
C1—C31.497 (6)C16—H16C0.9600
C1—C21.498 (6)C17—C181.491 (5)
C1—C41.532 (6)C17—H17A0.9700
C2—H2A0.9600C17—H17B0.9700
C2—H2B0.9600C18—C191.372 (5)
C2—H2C0.9600C18—C231.389 (4)
C3—H3A0.9600C19—C201.379 (6)
C3—H3B0.9600C19—H190.9300
C3—H3C0.9600C20—C211.377 (5)
C4—C51.506 (6)C20—H200.9300
C4—H4A0.9700C21—C221.375 (5)
C4—H4B0.9700C21—H210.9300
C5—C61.376 (6)C22—C231.379 (5)
C5—C101.389 (5)C25—C261.475 (7)
C6—C71.364 (6)C25—H25A0.9700
C6—H60.9300C25—H25B0.9700
C7—C81.385 (6)C26—H26A0.9600
C7—H70.9300C26—H26B0.9600
C8—C91.379 (6)C26—H26C0.9600
C10—O1—C1107.6 (3)C12—C13—H13B109.5
C11—O3—C9118.0 (2)H13A—C13—H13B109.5
C23—O4—C14107.3 (3)C12—C13—H13C109.5
C24—O5—C22116.8 (2)H13A—C13—H13C109.5
C11—N1—C12122.8 (3)H13B—C13—H13C109.5
C11—N1—H1118 (2)O4—C14—C16106.5 (3)
C12—N1—H1117 (2)O4—C14—C15106.0 (4)
C24—N2—C25121.2 (3)C16—C14—C15112.8 (4)
C24—N2—H2117 (3)O4—C14—C17105.4 (3)
C25—N2—H2121 (3)C16—C14—C17111.2 (4)
O1—C1—C3106.6 (3)C15—C14—C17114.2 (4)
O1—C1—C2106.3 (3)C14—C15—H15A109.5
C3—C1—C2114.3 (4)C14—C15—H15B109.5
O1—C1—C4105.5 (3)H15A—C15—H15B109.5
C3—C1—C4112.0 (4)C14—C15—H15C109.5
C2—C1—C4111.4 (4)H15A—C15—H15C109.5
C1—C2—H2A109.5H15B—C15—H15C109.5
C1—C2—H2B109.5C14—C16—H16A109.5
H2A—C2—H2B109.5C14—C16—H16B109.5
C1—C2—H2C109.5H16A—C16—H16B109.5
H2A—C2—H2C109.5C14—C16—H16C109.5
H2B—C2—H2C109.5H16A—C16—H16C109.5
C1—C3—H3A109.5H16B—C16—H16C109.5
C1—C3—H3B109.5C18—C17—C14103.7 (3)
H3A—C3—H3B109.5C18—C17—H17A111.0
C1—C3—H3C109.5C14—C17—H17A111.0
H3A—C3—H3C109.5C18—C17—H17B111.0
H3B—C3—H3C109.5C14—C17—H17B111.0
C5—C4—C1103.7 (3)H17A—C17—H17B109.0
C5—C4—H4A111.0C19—C18—C23120.5 (3)
C1—C4—H4A111.0C19—C18—C17131.5 (3)
C5—C4—H4B111.0C23—C18—C17108.0 (3)
C1—C4—H4B111.0C18—C19—C20118.9 (3)
H4A—C4—H4B109.0C18—C19—H19120.6
C6—C5—C10119.7 (4)C20—C19—H19120.6
C6—C5—C4133.1 (3)C21—C20—C19120.7 (4)
C10—C5—C4107.2 (3)C21—C20—H20119.7
C7—C6—C5119.8 (4)C19—C20—H20119.7
C7—C6—H6120.1C22—C21—C20120.7 (4)
C5—C6—H6120.1C22—C21—H21119.7
C6—C7—C8121.0 (4)C20—C21—H21119.7
C6—C7—H7119.5C21—C22—C23118.9 (3)
C8—C7—H7119.5C21—C22—O5120.6 (3)
C9—C8—C7119.7 (4)C23—C22—O5120.4 (3)
C9—C8—H8120.2O4—C23—C22125.4 (3)
C7—C8—H8120.2O4—C23—C18114.3 (3)
C8—C9—C10119.3 (3)C22—C23—C18120.3 (3)
C8—C9—O3119.8 (3)O6—C24—N2126.8 (3)
C10—C9—O3120.6 (3)O6—C24—O5123.6 (3)
O1—C10—C9125.1 (3)N2—C24—O5109.6 (3)
O1—C10—C5114.4 (3)N2—C25—C26110.6 (4)
C9—C10—C5120.5 (3)N2—C25—H25A109.5
O2—C11—N1127.4 (3)C26—C25—H25A109.5
O2—C11—O3122.7 (3)N2—C25—H25B109.5
N1—C11—O3109.9 (3)C26—C25—H25B109.5
N1—C12—C13111.3 (4)H25A—C25—H25B108.1
N1—C12—H12A109.4C25—C26—H26A109.5
C13—C12—H12A109.4C25—C26—H26B109.5
N1—C12—H12B109.4H26A—C26—H26B109.5
C13—C12—H12B109.4C25—C26—H26C109.5
H12A—C12—H12B108.0H26A—C26—H26C109.5
C12—C13—H13A109.5H26B—C26—H26C109.5
C10—O1—C1—C3131.3 (4)C23—O4—C14—C16107.5 (4)
C10—O1—C1—C2−106.3 (4)C23—O4—C14—C15−132.1 (4)
C10—O1—C1—C412.1 (4)C23—O4—C14—C17−10.7 (4)
O1—C1—C4—C5−12.4 (4)O4—C14—C17—C1811.4 (4)
C3—C1—C4—C5−128.0 (4)C16—C14—C17—C18−103.6 (4)
C2—C1—C4—C5102.6 (4)C15—C14—C17—C18127.4 (4)
C1—C4—C5—C6−173.3 (4)C14—C17—C18—C19172.3 (4)
C1—C4—C5—C108.7 (5)C14—C17—C18—C23−8.4 (4)
C10—C5—C6—C71.2 (6)C23—C18—C19—C20−1.4 (5)
C4—C5—C6—C7−176.6 (5)C17—C18—C19—C20177.9 (4)
C5—C6—C7—C80.5 (7)C18—C19—C20—C210.7 (6)
C6—C7—C8—C9−1.1 (7)C19—C20—C21—C22−0.4 (6)
C7—C8—C9—C10−0.1 (6)C20—C21—C22—C230.8 (5)
C7—C8—C9—O3174.4 (3)C20—C21—C22—O5176.5 (3)
C11—O3—C9—C8106.3 (4)C24—O5—C22—C2178.1 (4)
C11—O3—C9—C10−79.3 (4)C24—O5—C22—C23−106.3 (3)
C1—O1—C10—C9175.9 (3)C14—O4—C23—C22−174.8 (3)
C1—O1—C10—C5−6.9 (4)C14—O4—C23—C185.7 (4)
C8—C9—C10—O1178.9 (4)C21—C22—C23—O4179.0 (3)
O3—C9—C10—O14.4 (5)O5—C22—C23—O43.3 (5)
C8—C9—C10—C51.8 (5)C21—C22—C23—C18−1.6 (5)
O3—C9—C10—C5−172.6 (3)O5—C22—C23—C18−177.2 (3)
C6—C5—C10—O1−179.7 (4)C19—C18—C23—O4−178.6 (3)
C4—C5—C10—O1−1.4 (5)C17—C18—C23—O42.0 (4)
C6—C5—C10—C9−2.4 (6)C19—C18—C23—C221.9 (5)
C4—C5—C10—C9175.9 (3)C17—C18—C23—C22−177.5 (3)
C12—N1—C11—O2−6.4 (7)C25—N2—C24—O69.2 (6)
C12—N1—C11—O3173.9 (3)C25—N2—C24—O5−171.5 (3)
C9—O3—C11—O2−2.7 (5)C22—O5—C24—O67.3 (5)
C9—O3—C11—N1176.9 (3)C22—O5—C24—N2−172.0 (3)
C11—N1—C12—C13−96.9 (5)C24—N2—C25—C2689.0 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O60.82 (4)2.28 (4)3.024 (4)151 (3)
N2—H2···O2i0.84 (4)2.19 (4)2.985 (4)156 (3)
C19—H19···O5ii0.932.483.269 (4)143

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5190).

References

  • Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tomlin, C. (1994). The Pesticide Mannul. A World Compendium, 10th ed., pp. 152–153. Bath: The British Crop Protection Council, The Bath Press.
  • Xu, L.-Z., Yu, G.-P. & Yang, S.-H. (2005). Acta Cryst. E61, o1924–o1926.

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