organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aCollege of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China, and bSchool of Chemistry & Biological Engineering, Changsha University of Science & Technology, Changsha 410004, People's Republic of China
*Correspondence e-mail: liws01@hnu.cn

(Received 26 October 2009; accepted 27 October 2009; online 31 October 2009)

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[Tomlin, C. (1994). The Pesticide Mannul. A World Compendium, 10th ed., pp. 152-153. Bath: The British Crop Protection Council, The Bath Press.]). For a related structure, see Xu et al. (2005[Xu, L.-Z., Yu, G.-P. & Yang, S.-H. (2005). Acta Cryst. E61, o1924-o1926.]).

[Scheme 1]

Experimental

Crystal data
  • C13H17NO3

  • Mr = 235.28

  • Orthorhombic, P 21 21 21

  • 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[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.978, Tmax = 0.993

  • 20967 measured reflections

  • 3256 independent reflections

  • 2338 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O6 0.82 (4) 2.28 (4) 3.024 (4) 151 (3)
N2—H2⋯O2i 0.84 (4) 2.19 (4) 2.985 (4) 156 (3)
C19—H19⋯O5ii 0.93 2.48 3.269 (4) 143
Symmetry codes: (i) x-1, y, z; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Structure description top

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).

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

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. One molecule in the asymmetric unit of (I), showing d isplacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The other molecule in the asymmetric unit of (I), showing displacement ellipsoids drawn at the 30% level.
2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl N-ethylcarbamate top
Crystal data top
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 top
Rigaku Saturn CCD area-detector
diffractometer
3256 independent reflections
Radiation source: rotating anode2338 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.049
Detector resolution: 7.31 pixels mm-1θmax = 27.2°, θmin = 1.8°
ω and φ scansh = 1013
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1717
Tmin = 0.978, Tmax = 0.993l = 2123
20967 measured reflections
Refinement top
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) = 0.154 w = 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)
Crystal data top
C13H17NO3V = 2614.1 (10) Å3
Mr = 235.28Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 10.362 (2) ŵ = 0.09 mm1
b = 13.962 (3) ÅT = 293 K
c = 18.069 (4) Å0.26 × 0.20 × 0.08 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
3256 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
2338 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.993Rint = 0.049
20967 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.14 e Å3
3256 reflectionsΔρmin = 0.14 e Å3
322 parameters
Special details top

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) top
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)
H2A1.09890.41070.06140.162*
H2B1.20440.33030.06410.162*
H2C1.16470.37570.01190.162*
C30.9693 (6)0.2508 (4)0.0979 (3)0.127 (2)
H3A0.90360.20430.08750.190*
H3B1.03320.22320.12980.190*
H3C0.93120.30540.12170.190*
C41.0807 (5)0.1960 (3)0.0181 (2)0.0931 (13)
H4A1.05170.13600.00330.112*
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)
H190.56400.78400.08240.088*
C200.4699 (4)0.6584 (3)0.0705 (2)0.0833 (11)
H200.50220.62990.11320.100*
C210.3851 (3)0.6086 (3)0.0262 (2)0.0729 (10)
H210.36030.54690.03950.088*
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) top
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, º) top
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—C2106.3 (4)C23—O4—C14—C15132.1 (4)
C10—O1—C1—C412.1 (4)C23—O4—C14—C1710.7 (4)
O1—C1—C4—C512.4 (4)O4—C14—C17—C1811.4 (4)
C3—C1—C4—C5128.0 (4)C16—C14—C17—C18103.6 (4)
C2—C1—C4—C5102.6 (4)C15—C14—C17—C18127.4 (4)
C1—C4—C5—C6173.3 (4)C14—C17—C18—C19172.3 (4)
C1—C4—C5—C108.7 (5)C14—C17—C18—C238.4 (4)
C10—C5—C6—C71.2 (6)C23—C18—C19—C201.4 (5)
C4—C5—C6—C7176.6 (5)C17—C18—C19—C20177.9 (4)
C5—C6—C7—C80.5 (7)C18—C19—C20—C210.7 (6)
C6—C7—C8—C91.1 (7)C19—C20—C21—C220.4 (6)
C7—C8—C9—C100.1 (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—C1079.3 (4)C24—O5—C22—C23106.3 (3)
C1—O1—C10—C9175.9 (3)C14—O4—C23—C22174.8 (3)
C1—O1—C10—C56.9 (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—C181.6 (5)
O3—C9—C10—C5172.6 (3)O5—C22—C23—C18177.2 (3)
C6—C5—C10—O1179.7 (4)C19—C18—C23—O4178.6 (3)
C4—C5—C10—O11.4 (5)C17—C18—C23—O42.0 (4)
C6—C5—C10—C92.4 (6)C19—C18—C23—C221.9 (5)
C4—C5—C10—C9175.9 (3)C17—C18—C23—C22177.5 (3)
C12—N1—C11—O26.4 (7)C25—N2—C24—O69.2 (6)
C12—N1—C11—O3173.9 (3)C25—N2—C24—O5171.5 (3)
C9—O3—C11—O22.7 (5)C22—O5—C24—O67.3 (5)
C9—O3—C11—N1176.9 (3)C22—O5—C24—N2172.0 (3)
C11—N1—C12—C1396.9 (5)C24—N2—C25—C2689.0 (5)
Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (ii) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formulaC13H17NO3
Mr235.28
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)10.362 (2), 13.962 (3), 18.069 (4)
V3)2614.1 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.26 × 0.20 × 0.08
Data collection
DiffractometerRigaku Saturn CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.978, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
20967, 3256, 2338
Rint0.049
(sin θ/λ)max1)0.642
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.154, 1.08
No. of reflections3256
No. of parameters322
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.14, 0.14

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (ii) x+1/2, y+3/2, z.
 

Acknowledgements

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

References

First citationRigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTomlin, C. (1994). The Pesticide Mannul. A World Compendium, 10th ed., pp. 152–153. Bath: The British Crop Protection Council, The Bath Press.  Google Scholar
First citationXu, L.-Z., Yu, G.-P. & Yang, S.-H. (2005). Acta Cryst. E61, o1924–o1926.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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