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ISSN: 2056-9890

Ethyl 4-{2,6-di­chloro-4-[3-(2,6-di­fluoro­benzo­yl)ureido]phen­­oxy}butanoate

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technolgy, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China
*Correspondence e-mail: fangshi.li@njut.edu.cn

(Received 16 July 2008; accepted 3 August 2008; online 9 August 2008)

The title compound, C20H18Cl2F2N2O5, is considered to belong to the fourth generation of insecticides with properties such as high selectivity, low acute toxicity for mammals and high biological activity. An intramolecular N—H⋯O hydrogen bond results in the formation of a six-membered ring. In the crystal structure, intermolecular N—H⋯O and C—H⋯F hydrogen bonds link the molecules.

Related literature

For related literature, see: Wang et al. (1998[Wang, S., Allan, R. D., Skerritt, J. H. & Kennedy, I. R. (1998). J. Agric. Food Chem. 46, 3330-3338.], 1999[Wang, S., Allan, R. D., Skerritt, J. H. & Kennedy, I. R. (1999). J. Agric. Food Chem. 47, 3416-3424.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18Cl2F2N2O5

  • Mr = 475.26

  • Monoclinic, P 21 /n

  • a = 11.262 (2) Å

  • b = 10.463 (2) Å

  • c = 18.613 (4) Å

  • β = 98.78 (3)°

  • V = 2167.5 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.35 mm−1

  • T = 293 (2) K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.872, Tmax = 0.933

  • 4157 measured reflections

  • 3944 independent reflections

  • 2385 reflections with I > 2σ(I)

  • Rint = 0.041

  • 3 standard reflections every 200 reflections intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.082

  • wR(F2) = 0.290

  • S = 1.13

  • 3944 reflections

  • 268 parameters

  • H-atom parameters constrained

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.99 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯O4i 0.86 2.00 2.856 (6) 173
C5—H5A⋯F2ii 0.97 2.44 3.201 (8) 135
N1—H1A⋯O5 0.86 1.97 2.675 (7) 138
Symmetry codes: (i) -x-1, -y, -z; (ii) -x, -y, -z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXL97; software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound is generally recognized as an insect growth regulator that interferes with chitin synthesis in target pests, causing death or abortive development (Wang et al. 1998). Bonding dimensions conform to expected values (Allen et al., 1987).

Related literature top

For related literature, see: Wang et al. (1998, 1999). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to a literature method (Wang et al. 1999). The crystals suitable for X-ray analysis were obtained by dissolving it (0.1 g) in acetonitrile (25 ml) and evaporating the solvent slowly at room temperature for about 6 d.

Refinement top

H atoms were positioned geometrically, with C—H distances of 0.93 and of 0.97 Å for aromatic and methyl H atoms and with N—H = 0.86 Å for amido H atoms. All H atoms were constrained to ride on their parent atoms with Uiso(H) = xUeq(C,N), where x = 1.2 for all H atoms.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. N—H···O intramolecular hydrogen bond is shown by dashed line.
[Figure 2] Fig. 2. A packing diagram detail from the crystal structure. N—H···O and C—H···F intermolecular hydrogen bonds are shown by dashed lines.
Ethyl 4-{2,6-dichloro-4-[3-(2,6-difluorobenzoyl)ureido]phenoxy}butanoate top
Crystal data top
C20H18Cl2F2N2O5F(000) = 976
Mr = 475.26Dx = 1.456 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 11.262 (2) Åθ = 9–12°
b = 10.463 (2) ŵ = 0.35 mm1
c = 18.613 (4) ÅT = 293 K
β = 98.78 (3)°Block, colourless
V = 2167.5 (8) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
2385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 25.3°, θmin = 2.0°
ω/2θ scansh = 1313
Absorption correction: ψ scan
(North et al., 1968)
k = 012
Tmin = 0.872, Tmax = 0.933l = 022
4157 measured reflections3 standard reflections every 200 reflections
3944 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.082Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.290H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.1372P)2 + 4.2262P]
where P = (Fo2 + 2Fc2)/3
3944 reflections(Δ/σ)max < 0.001
268 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.99 e Å3
Crystal data top
C20H18Cl2F2N2O5V = 2167.5 (8) Å3
Mr = 475.26Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.262 (2) ŵ = 0.35 mm1
b = 10.463 (2) ÅT = 293 K
c = 18.613 (4) Å0.40 × 0.30 × 0.20 mm
β = 98.78 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
2385 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.041
Tmin = 0.872, Tmax = 0.9333 standard reflections every 200 reflections
4157 measured reflections intensity decay: none
3944 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0820 restraints
wR(F2) = 0.290H-atom parameters constrained
S = 1.13Δρmax = 0.77 e Å3
3944 reflectionsΔρmin = 0.99 e Å3
268 parameters
Special details top

Experimental. (North et al., 1968)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.23061 (14)0.09615 (16)0.16895 (10)0.0611 (5)
Cl20.02268 (15)0.30602 (15)0.02019 (10)0.0672 (6)
F10.5092 (6)0.3204 (6)0.2109 (3)0.127 (2)
F20.5604 (4)0.3418 (6)0.0403 (2)0.0995 (17)
N10.2177 (4)0.0877 (5)0.0826 (3)0.0473 (12)
H1A0.21320.16060.10420.057*
O10.5929 (5)0.0111 (5)0.2331 (3)0.0813 (16)
C10.7375 (8)0.1501 (10)0.2970 (5)0.095
H1B0.76220.19380.34210.142*
H1C0.71730.21160.25880.142*
H1D0.80190.09690.28610.142*
N20.4207 (4)0.1420 (5)0.0532 (3)0.0481 (12)
H2A0.49080.12020.03160.058*
O20.4801 (5)0.1199 (6)0.2895 (3)0.092
C20.6371 (8)0.0743 (9)0.3027 (4)0.092 (3)
H2B0.57380.12710.31700.110*
H2C0.65830.01000.34000.110*
O30.2254 (3)0.1568 (4)0.09703 (19)0.0458 (10)
C30.5158 (6)0.0854 (7)0.2341 (3)0.0544 (16)
O40.3529 (4)0.0477 (4)0.0170 (2)0.0578 (12)
C40.4795 (5)0.1407 (6)0.1610 (4)0.0545 (16)
H4A0.55120.16380.14110.065*
H4B0.43760.07570.12970.065*
O50.3196 (4)0.3054 (5)0.1175 (3)0.0775 (16)
C50.3991 (5)0.2578 (6)0.1597 (4)0.0513 (15)
H5A0.40370.30580.11560.062*
H5B0.42930.31210.20060.062*
C60.2705 (5)0.2267 (6)0.1628 (3)0.0436 (13)
H6A0.22460.30460.16550.052*
H6B0.26400.17510.20530.052*
C70.1154 (5)0.1029 (6)0.0964 (3)0.0419 (13)
C80.1028 (5)0.0189 (6)0.1269 (3)0.0431 (13)
C90.0055 (5)0.0791 (6)0.1230 (3)0.0455 (14)
H9A0.01080.15910.14400.055*
C100.1091 (5)0.0182 (5)0.0867 (3)0.0440 (14)
C110.1009 (5)0.1023 (5)0.0560 (3)0.0453 (14)
H11A0.16880.14370.03230.054*
C120.0113 (5)0.1586 (5)0.0618 (3)0.0464 (14)
C130.3273 (5)0.0529 (6)0.0489 (3)0.0428 (13)
C140.4138 (6)0.2591 (6)0.0874 (3)0.0509 (15)
C150.5308 (5)0.3250 (5)0.0855 (3)0.0431 (13)
C160.5738 (7)0.3548 (7)0.1491 (4)0.0622 (18)
C170.6834 (8)0.4151 (7)0.1493 (5)0.076 (2)
H17A0.71080.43250.19300.091*
C180.7493 (7)0.4481 (7)0.0858 (5)0.074 (2)
H18A0.82360.48710.08540.089*
C190.7083 (6)0.4251 (7)0.0223 (4)0.071 (2)
H19A0.75350.44980.02150.085*
C200.6010 (6)0.3657 (7)0.0230 (3)0.0574 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0473 (9)0.0581 (10)0.0746 (11)0.0088 (7)0.0015 (7)0.0205 (8)
Cl20.0649 (11)0.0426 (9)0.0892 (13)0.0079 (8)0.0042 (9)0.0222 (8)
F10.181 (6)0.146 (5)0.057 (3)0.081 (5)0.027 (3)0.020 (3)
F20.104 (3)0.145 (5)0.048 (2)0.052 (3)0.006 (2)0.015 (3)
N10.047 (3)0.041 (3)0.050 (3)0.010 (2)0.007 (2)0.010 (2)
O10.092 (4)0.072 (3)0.068 (3)0.033 (3)0.024 (3)0.011 (3)
C10.0950.0950.0950.0000.0140.000
N20.048 (3)0.038 (3)0.056 (3)0.009 (2)0.001 (2)0.010 (2)
O20.0920.0920.0920.0000.0140.000
C20.109 (7)0.085 (6)0.068 (5)0.039 (5)0.029 (5)0.001 (4)
O30.042 (2)0.058 (3)0.038 (2)0.0023 (19)0.0072 (16)0.0027 (18)
C30.055 (4)0.060 (4)0.047 (4)0.001 (3)0.006 (3)0.015 (3)
O40.048 (2)0.041 (2)0.077 (3)0.0065 (19)0.015 (2)0.021 (2)
C40.045 (3)0.056 (4)0.063 (4)0.008 (3)0.009 (3)0.001 (3)
O50.053 (3)0.058 (3)0.111 (4)0.000 (2)0.020 (3)0.034 (3)
C50.038 (3)0.052 (4)0.063 (4)0.002 (3)0.008 (3)0.001 (3)
C60.043 (3)0.042 (3)0.045 (3)0.003 (3)0.004 (2)0.001 (3)
C70.041 (3)0.048 (3)0.036 (3)0.002 (3)0.004 (2)0.004 (3)
C80.046 (3)0.043 (3)0.040 (3)0.009 (3)0.004 (2)0.003 (3)
C90.052 (3)0.043 (3)0.039 (3)0.002 (3)0.001 (3)0.008 (3)
C100.047 (3)0.040 (3)0.041 (3)0.002 (3)0.004 (2)0.001 (3)
C110.045 (3)0.038 (3)0.051 (3)0.002 (3)0.001 (3)0.006 (3)
C120.054 (3)0.035 (3)0.049 (3)0.001 (3)0.005 (3)0.000 (3)
C130.040 (3)0.043 (3)0.043 (3)0.011 (3)0.004 (2)0.003 (3)
C140.053 (4)0.046 (4)0.051 (4)0.001 (3)0.003 (3)0.002 (3)
C150.044 (3)0.037 (3)0.049 (3)0.005 (2)0.008 (3)0.001 (3)
C160.091 (5)0.051 (4)0.049 (4)0.010 (4)0.024 (4)0.011 (3)
C170.101 (6)0.055 (4)0.085 (6)0.026 (4)0.056 (5)0.005 (4)
C180.060 (4)0.050 (4)0.114 (7)0.015 (3)0.020 (4)0.022 (4)
C190.062 (4)0.073 (5)0.074 (5)0.016 (4)0.001 (4)0.019 (4)
C200.059 (4)0.061 (4)0.050 (4)0.007 (3)0.002 (3)0.018 (3)
Geometric parameters (Å, º) top
Cl1—C81.730 (6)C4—H4B0.9700
Cl2—C121.739 (6)O5—C141.222 (7)
F1—C161.314 (9)C5—C61.494 (8)
F2—C201.350 (7)C5—H5A0.9700
N1—C131.347 (7)C5—H5B0.9700
N1—C101.414 (7)C6—H6A0.9700
N1—H1A0.8600C6—H6B0.9700
O1—C31.333 (8)C7—C121.379 (8)
O1—C21.472 (9)C7—C81.410 (8)
C1—C21.399 (11)C8—C91.365 (8)
C1—H1B0.9600C9—C101.408 (8)
C1—H1C0.9600C9—H9A0.9300
C1—H1D0.9600C10—C111.394 (8)
N2—C141.378 (8)C11—C121.383 (8)
N2—C131.417 (7)C11—H11A0.9300
N2—H2A0.8600C14—C151.482 (8)
O2—C31.217 (8)C15—C201.372 (9)
C2—H2B0.9700C15—C161.381 (8)
C2—H2C0.9700C16—C171.386 (10)
O3—C71.360 (6)C17—C181.342 (11)
O3—C61.449 (7)C17—H17A0.9300
C3—C41.477 (9)C18—C191.354 (10)
O4—C131.223 (7)C18—H18A0.9300
C4—C51.522 (9)C19—C201.358 (9)
C4—H4A0.9700C19—H19A0.9300
C13—N1—C10127.6 (5)O3—C7—C8121.3 (5)
C13—N1—H1A116.2C12—C7—C8116.1 (5)
C10—N1—H1A116.2C9—C8—C7122.6 (5)
C3—O1—C2117.4 (6)C9—C8—Cl1118.9 (4)
C2—C1—H1B109.5C7—C8—Cl1118.4 (4)
C2—C1—H1C109.5C8—C9—C10119.1 (5)
H1B—C1—H1C109.5C8—C9—H9A120.5
C2—C1—H1D109.5C10—C9—H9A120.5
H1B—C1—H1D109.5C11—C10—C9120.2 (5)
H1C—C1—H1D109.5C11—C10—N1123.7 (5)
C14—N2—C13128.4 (5)C9—C10—N1116.1 (5)
C14—N2—H2A115.8C12—C11—C10118.1 (5)
C13—N2—H2A115.8C12—C11—H11A121.0
C1—C2—O1110.9 (8)C10—C11—H11A121.0
C1—C2—H2B109.5C7—C12—C11123.9 (5)
O1—C2—H2B109.5C7—C12—Cl2117.9 (5)
C1—C2—H2C109.5C11—C12—Cl2118.1 (5)
O1—C2—H2C109.5O4—C13—N1126.2 (5)
H2B—C2—H2C108.1O4—C13—N2118.2 (5)
C7—O3—C6114.7 (4)N1—C13—N2115.6 (5)
O2—C3—O1122.5 (7)O5—C14—N2123.3 (6)
O2—C3—C4125.6 (6)O5—C14—C15122.2 (6)
O1—C3—C4111.9 (5)N2—C14—C15114.5 (5)
C3—C4—C5114.3 (6)C20—C15—C16115.1 (6)
C3—C4—H4A108.7C20—C15—C14124.0 (5)
C5—C4—H4A108.7C16—C15—C14120.8 (6)
C3—C4—H4B108.7F1—C16—C15117.9 (6)
C5—C4—H4B108.7F1—C16—C17119.7 (6)
H4A—C4—H4B107.6C15—C16—C17122.3 (7)
C6—C5—C4113.7 (5)C18—C17—C16119.2 (7)
C6—C5—H5A108.8C18—C17—H17A120.4
C4—C5—H5A108.8C16—C17—H17A120.4
C6—C5—H5B108.8C17—C18—C19120.4 (7)
C4—C5—H5B108.8C17—C18—H18A119.8
H5A—C5—H5B107.7C19—C18—H18A119.8
O3—C6—C5107.1 (5)C18—C19—C20119.7 (7)
O3—C6—H6A110.3C18—C19—H19A120.1
C5—C6—H6A110.3C20—C19—H19A120.1
O3—C6—H6B110.3F2—C20—C19119.8 (6)
C5—C6—H6B110.3F2—C20—C15117.1 (6)
H6A—C6—H6B108.5C19—C20—C15123.2 (6)
O3—C7—C12122.4 (5)
C3—O1—C2—C1165.2 (8)C10—C11—C12—C70.4 (9)
C2—O1—C3—O21.5 (10)C10—C11—C12—Cl2177.4 (4)
C2—O1—C3—C4179.5 (7)C10—N1—C13—O42.0 (10)
O2—C3—C4—C55.6 (10)C10—N1—C13—N2179.6 (5)
O1—C3—C4—C5175.5 (5)C14—N2—C13—O4178.4 (6)
C3—C4—C5—C679.5 (7)C14—N2—C13—N10.2 (9)
C7—O3—C6—C5169.7 (5)C13—N2—C14—O53.4 (10)
C4—C5—C6—O364.3 (7)C13—N2—C14—C15176.1 (5)
C6—O3—C7—C1299.1 (6)O5—C14—C15—C20116.7 (8)
C6—O3—C7—C885.8 (6)N2—C14—C15—C2063.8 (8)
O3—C7—C8—C9175.6 (5)O5—C14—C15—C1660.2 (9)
C12—C7—C8—C90.3 (8)N2—C14—C15—C16119.3 (6)
O3—C7—C8—Cl12.8 (7)C20—C15—C16—F1178.7 (7)
C12—C7—C8—Cl1178.2 (4)C14—C15—C16—F11.5 (10)
C7—C8—C9—C100.5 (9)C20—C15—C16—C173.5 (10)
Cl1—C8—C9—C10177.9 (4)C14—C15—C16—C17179.3 (6)
C8—C9—C10—C110.7 (9)F1—C16—C17—C18179.1 (8)
C8—C9—C10—N1178.0 (5)C15—C16—C17—C181.3 (12)
C13—N1—C10—C111.2 (9)C16—C17—C18—C191.3 (12)
C13—N1—C10—C9177.4 (6)C17—C18—C19—C201.4 (12)
C9—C10—C11—C120.6 (9)C18—C19—C20—F2179.5 (7)
N1—C10—C11—C12178.0 (5)C18—C19—C20—C151.1 (11)
O3—C7—C12—C11175.5 (5)C16—C15—C20—F2178.1 (6)
C8—C7—C12—C110.2 (9)C14—C15—C20—F21.0 (10)
O3—C7—C12—Cl22.2 (8)C16—C15—C20—C193.4 (10)
C8—C7—C12—Cl2177.5 (4)C14—C15—C20—C19179.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O4i0.862.002.856 (6)173
C5—H5A···F2ii0.972.443.201 (8)135
N1—H1A···O50.861.972.675 (7)138
Symmetry codes: (i) x1, y, z; (ii) x, y, z.

Experimental details

Crystal data
Chemical formulaC20H18Cl2F2N2O5
Mr475.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)11.262 (2), 10.463 (2), 18.613 (4)
β (°) 98.78 (3)
V3)2167.5 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.872, 0.933
No. of measured, independent and
observed [I > 2σ(I)] reflections
4157, 3944, 2385
Rint0.041
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.082, 0.290, 1.13
No. of reflections3944
No. of parameters268
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.77, 0.99

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Cl1—C81.730 (6)N2—C141.378 (8)
Cl2—C121.739 (6)N2—C131.417 (7)
F1—C161.314 (9)O2—C31.217 (8)
F2—C201.350 (7)O3—C71.360 (6)
N1—C131.347 (7)O3—C61.449 (7)
N1—C101.414 (7)O4—C131.223 (7)
O1—C31.333 (8)O5—C141.222 (7)
O1—C21.472 (9)
C13—N1—C10127.6 (5)C9—C10—N1116.1 (5)
C10—N1—H1A116.2C7—C12—Cl2117.9 (5)
C3—O1—C2117.4 (6)C11—C12—Cl2118.1 (5)
C1—C2—O1110.9 (8)O4—C13—N1126.2 (5)
C7—O3—C6114.7 (4)O4—C13—N2118.2 (5)
O2—C3—O1122.5 (7)N1—C13—N2115.6 (5)
O2—C3—C4125.6 (6)O5—C14—N2123.3 (6)
O1—C3—C4111.9 (5)O5—C14—C15122.2 (6)
O3—C6—C5107.1 (5)N2—C14—C15114.5 (5)
O3—C7—C12122.4 (5)F1—C16—C15117.9 (6)
O3—C7—C8121.3 (5)F1—C16—C17119.7 (6)
C9—C8—Cl1118.9 (4)F2—C20—C19119.8 (6)
C7—C8—Cl1118.4 (4)F2—C20—C15117.1 (6)
C11—C10—N1123.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O4i0.862.002.856 (6)173
C5—H5A···F2ii0.972.443.201 (8)135
N1—H1A···O50.861.972.675 (7)138
Symmetry codes: (i) x1, y, z; (ii) x, y, z.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, S., Allan, R. D., Skerritt, J. H. & Kennedy, I. R. (1998). J. Agric. Food Chem. 46, 3330–3338.  Web of Science CrossRef CAS Google Scholar
First citationWang, S., Allan, R. D., Skerritt, J. H. & Kennedy, I. R. (1999). J. Agric. Food Chem. 47, 3416–3424.  Web of Science CrossRef PubMed CAS Google Scholar

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