organic compounds
2-(Methoxyimino)-2-{2-[(2-methylphenoxy)methyl]phenyl}acetohydrazide
aX-ray Crystallography Laboratory, Post-Graduate Department of Physics and Electronics, University of Jammu, Jammu Tawi 180 006, India, bDepartment of Chemistry, Shivaji University, Kolhapur, 416 004, India, and cNational Research Centre for Grapes, Pune 412 307, India
*Correspondence e-mail: rkvk.paper11@gmail.com
In the title molecule, C17H19N3O3, the dihedral angle between the two benzene rings is 57.17 (5)°. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds connect molecules to form chains along [001]. In addition, a weak C—H⋯π interaction is observed.
Related literature
For the biological activities of kresoxim-methyl {methyl 2(E)-methoxyimino-2-[2-(2-tolyloxymethyl)phenyl] acetate}, which is a starting material in the synthesis of the title compound, see: Anke et al. (1977); Balba (2007); Ichinari et al. (1999); Grossmann & Retzlaff (1997); Ypema (1998). For the of kresoxim-methyl, see: Chopra et al. (2004).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S160053681203070X/lh5499sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203070X/lh5499Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681203070X/lh5499Isup3.cml
Kresoxim-methyl (0.313 g, 0.001 mol) was dissolved in 5 ml methanol and to it hydrazine hydrate (0.1 g, 0.002 mol) solution was added and refluxed at 343K for 1 h. The reaction mixture was then cooled and solvent was removed under reduced presser to give a solid product. The compound was dissolved in methanol, and by the process of slow evaporation this crystalline compound was separated out, m.p. 397K.
H atoms bonded to N atoms were located in a difference map and refined independently with the constraint of N—H = 0.86 (1)Å. Other H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Kresoxim-methyl is an active agrochemical (Chopra et al., 2004), strobilurin fungicide (Anke et al., 1977), with broad spectrum biological activity (Ypema, 1998; Ichinari et al., 1999; Grossmann & Retzlaff 1997). This type of compound is easily metabolized in nature as well as in living systems, and that is the reason studies on their fate in soil, plants and animal systems (Balba, 2007) are very important. Herein, we present the
of the title compound (I) which was synthesized from kresoxim-methyl.In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related structure (Chopra et al., 2004). The dihedral angles formed by the two benzene rings (C8-C13/C16-C21) is 57.17 (5)°. In the crystal, molecules are connected by N—H···O and N—H···N hydrogen bonds into chains along [001] (Fig. 2). In addition a weak C—H···π interaction is observed.
For the biological activities of kresoxim-methyl {methyl 2(E)-methoxyimino-2-[2-(2-tolyloxymethyl)phenyl] acetate}, which is a starting material in the synthesis of the title compound, see: Anke et al. (1977); Balba (2007); Ichinari et al. (1999); Grossmann & Retzlaff (1997); Ypema (1998). For the
of kresoxim-methyl, see: Chopra et al. (2004).Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).C17H19N3O3 | F(000) = 1328 |
Mr = 313.35 | Dx = 1.290 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 21236 reflections |
a = 21.4015 (6) Å | θ = 3.5–29.1° |
b = 20.7277 (4) Å | µ = 0.09 mm−1 |
c = 7.6975 (2) Å | T = 293 K |
β = 109.103 (3)° | Block, white |
V = 3226.60 (14) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 8 |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 3174 independent reflections |
Radiation source: fine-focus sealed tube | 2532 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 16.1049 pixels mm-1 | θmax = 26.0°, θmin = 3.5° |
ω scan | h = −26→26 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −25→25 |
Tmin = 0.906, Tmax = 1.000 | l = −9→9 |
55120 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0448P)2 + 1.9045P] where P = (Fo2 + 2Fc2)/3 |
3174 reflections | (Δ/σ)max = 0.001 |
222 parameters | Δρmax = 0.18 e Å−3 |
3 restraints | Δρmin = −0.17 e Å−3 |
C17H19N3O3 | V = 3226.60 (14) Å3 |
Mr = 313.35 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.4015 (6) Å | µ = 0.09 mm−1 |
b = 20.7277 (4) Å | T = 293 K |
c = 7.6975 (2) Å | 0.3 × 0.2 × 0.2 mm |
β = 109.103 (3)° |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 3174 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 2532 reflections with I > 2σ(I) |
Tmin = 0.906, Tmax = 1.000 | Rint = 0.042 |
55120 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 3 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.18 e Å−3 |
3174 reflections | Δρmin = −0.17 e Å−3 |
222 parameters |
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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. |
x | y | z | Uiso*/Ueq | ||
N3 | 0.10242 (6) | 0.35418 (5) | 0.94034 (15) | 0.0383 (3) | |
N6 | 0.08078 (6) | 0.46145 (6) | 0.74149 (16) | 0.0391 (3) | |
N7 | 0.06911 (8) | 0.51996 (6) | 0.64119 (18) | 0.0453 (3) | |
O15 | 0.23561 (6) | 0.35236 (5) | 0.70574 (15) | 0.0510 (3) | |
O4 | 0.11743 (6) | 0.29666 (5) | 1.03992 (13) | 0.0466 (3) | |
O1 | 0.06825 (6) | 0.40146 (5) | 0.48718 (13) | 0.0521 (3) | |
C17 | 0.28955 (8) | 0.44911 (8) | 0.6901 (2) | 0.0519 (4) | |
C18 | 0.34451 (11) | 0.48795 (10) | 0.7505 (3) | 0.0694 (6) | |
H18 | 0.3437 | 0.5282 | 0.6965 | 0.083* | |
C19 | 0.40054 (11) | 0.46909 (12) | 0.8882 (3) | 0.0808 (7) | |
H19 | 0.4372 | 0.4961 | 0.9252 | 0.097* | |
C20 | 0.40213 (10) | 0.41013 (11) | 0.9710 (3) | 0.0706 (6) | |
H20 | 0.4400 | 0.3972 | 1.0645 | 0.085* | |
C21 | 0.34756 (8) | 0.36974 (9) | 0.9158 (2) | 0.0546 (4) | |
H21 | 0.3484 | 0.3300 | 0.9728 | 0.066* | |
C16 | 0.29186 (8) | 0.38918 (8) | 0.7750 (2) | 0.0444 (4) | |
C22 | 0.22894 (10) | 0.47007 (10) | 0.5382 (3) | 0.0728 (6) | |
H22A | 0.2339 | 0.5142 | 0.5069 | 0.109* | |
H22B | 0.1910 | 0.4662 | 0.5780 | 0.109* | |
H22C | 0.2231 | 0.4432 | 0.4324 | 0.109* | |
C14 | 0.23124 (8) | 0.29575 (7) | 0.8055 (2) | 0.0453 (4) | |
H14A | 0.2306 | 0.3074 | 0.9270 | 0.054* | |
H14B | 0.2695 | 0.2685 | 0.8198 | 0.054* | |
C13 | 0.16963 (7) | 0.26008 (7) | 0.70408 (19) | 0.0382 (3) | |
C12 | 0.17407 (9) | 0.20035 (8) | 0.6249 (2) | 0.0523 (4) | |
H12 | 0.2155 | 0.1838 | 0.6353 | 0.063* | |
C11 | 0.11869 (11) | 0.16554 (8) | 0.5321 (3) | 0.0603 (5) | |
H11 | 0.1228 | 0.1257 | 0.4814 | 0.072* | |
C10 | 0.05738 (10) | 0.18966 (9) | 0.5143 (2) | 0.0593 (5) | |
H10 | 0.0198 | 0.1663 | 0.4507 | 0.071* | |
C9 | 0.05121 (8) | 0.24886 (8) | 0.5911 (2) | 0.0473 (4) | |
H9 | 0.0094 | 0.2650 | 0.5783 | 0.057* | |
C8 | 0.10689 (7) | 0.28413 (6) | 0.68670 (18) | 0.0347 (3) | |
C2 | 0.09848 (7) | 0.34665 (6) | 0.77269 (18) | 0.0320 (3) | |
C5 | 0.11414 (11) | 0.30815 (9) | 1.2204 (2) | 0.0608 (5) | |
H5A | 0.1481 | 0.3382 | 1.2840 | 0.091* | |
H5B | 0.1205 | 0.2683 | 1.2873 | 0.091* | |
H5C | 0.0716 | 0.3257 | 1.2106 | 0.091* | |
C1 | 0.08095 (7) | 0.40622 (7) | 0.65305 (18) | 0.0334 (3) | |
H61 | 0.0840 (8) | 0.4629 (7) | 0.8568 (13) | 0.041 (4)* | |
H71 | 0.0964 (9) | 0.5477 (8) | 0.707 (3) | 0.081 (7)* | |
H72 | 0.0295 (6) | 0.5333 (11) | 0.627 (3) | 0.090 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N3 | 0.0523 (7) | 0.0327 (6) | 0.0321 (6) | 0.0099 (5) | 0.0169 (5) | 0.0061 (5) |
N6 | 0.0587 (8) | 0.0320 (6) | 0.0273 (6) | 0.0039 (5) | 0.0149 (6) | 0.0027 (5) |
N7 | 0.0656 (10) | 0.0306 (7) | 0.0381 (7) | 0.0039 (7) | 0.0147 (7) | 0.0031 (5) |
O15 | 0.0515 (7) | 0.0461 (6) | 0.0510 (7) | −0.0027 (5) | 0.0109 (5) | 0.0143 (5) |
O4 | 0.0752 (8) | 0.0367 (6) | 0.0327 (5) | 0.0146 (5) | 0.0244 (5) | 0.0094 (4) |
O1 | 0.0866 (9) | 0.0427 (6) | 0.0291 (5) | 0.0151 (6) | 0.0215 (5) | 0.0035 (4) |
C17 | 0.0549 (10) | 0.0522 (10) | 0.0582 (10) | −0.0013 (8) | 0.0317 (8) | 0.0044 (8) |
C18 | 0.0698 (14) | 0.0621 (12) | 0.0891 (15) | −0.0130 (10) | 0.0435 (12) | −0.0013 (11) |
C19 | 0.0598 (13) | 0.0881 (16) | 0.1030 (18) | −0.0239 (12) | 0.0382 (13) | −0.0213 (14) |
C20 | 0.0448 (11) | 0.0892 (16) | 0.0760 (13) | 0.0057 (10) | 0.0172 (9) | −0.0183 (12) |
C21 | 0.0504 (10) | 0.0566 (10) | 0.0577 (10) | 0.0075 (8) | 0.0188 (8) | −0.0050 (8) |
C16 | 0.0443 (9) | 0.0451 (9) | 0.0491 (9) | 0.0019 (7) | 0.0226 (7) | −0.0006 (7) |
C22 | 0.0763 (14) | 0.0638 (12) | 0.0795 (14) | −0.0005 (10) | 0.0271 (11) | 0.0313 (10) |
C14 | 0.0445 (9) | 0.0439 (9) | 0.0489 (9) | 0.0101 (7) | 0.0171 (7) | 0.0141 (7) |
C13 | 0.0481 (9) | 0.0341 (7) | 0.0373 (7) | 0.0075 (6) | 0.0209 (6) | 0.0088 (6) |
C12 | 0.0712 (12) | 0.0402 (9) | 0.0566 (10) | 0.0157 (8) | 0.0360 (9) | 0.0073 (7) |
C11 | 0.0990 (16) | 0.0358 (9) | 0.0598 (11) | −0.0025 (9) | 0.0446 (11) | −0.0069 (8) |
C10 | 0.0804 (13) | 0.0514 (10) | 0.0523 (10) | −0.0246 (9) | 0.0303 (9) | −0.0129 (8) |
C9 | 0.0503 (9) | 0.0516 (9) | 0.0451 (9) | −0.0055 (7) | 0.0225 (7) | −0.0034 (7) |
C8 | 0.0457 (8) | 0.0328 (7) | 0.0299 (7) | 0.0028 (6) | 0.0184 (6) | 0.0041 (5) |
C2 | 0.0339 (7) | 0.0331 (7) | 0.0307 (7) | 0.0043 (5) | 0.0130 (6) | 0.0027 (5) |
C5 | 0.0999 (15) | 0.0554 (10) | 0.0335 (8) | 0.0123 (10) | 0.0307 (9) | 0.0089 (7) |
C1 | 0.0367 (7) | 0.0359 (7) | 0.0297 (7) | 0.0058 (6) | 0.0136 (6) | 0.0028 (5) |
N3—C2 | 1.2750 (17) | C22—H22A | 0.9600 |
N3—O4 | 1.3968 (14) | C22—H22B | 0.9600 |
N6—C1 | 1.3326 (17) | C22—H22C | 0.9600 |
N6—N7 | 1.4153 (17) | C14—C13 | 1.490 (2) |
N6—H61 | 0.868 (9) | C14—H14A | 0.9700 |
N7—H71 | 0.858 (10) | C14—H14B | 0.9700 |
N7—H72 | 0.864 (10) | C13—C12 | 1.397 (2) |
O15—C16 | 1.3767 (19) | C13—C8 | 1.397 (2) |
O15—C14 | 1.4222 (17) | C12—C11 | 1.372 (3) |
O4—C5 | 1.4335 (18) | C12—H12 | 0.9300 |
O1—C1 | 1.2192 (16) | C11—C10 | 1.369 (3) |
C17—C18 | 1.375 (3) | C11—H11 | 0.9300 |
C17—C16 | 1.397 (2) | C10—C9 | 1.387 (2) |
C17—C22 | 1.498 (3) | C10—H10 | 0.9300 |
C18—C19 | 1.372 (3) | C9—C8 | 1.387 (2) |
C18—H18 | 0.9300 | C9—H9 | 0.9300 |
C19—C20 | 1.374 (3) | C8—C2 | 1.4926 (18) |
C19—H19 | 0.9300 | C2—C1 | 1.5123 (18) |
C20—C21 | 1.386 (3) | C5—H5A | 0.9600 |
C20—H20 | 0.9300 | C5—H5B | 0.9600 |
C21—C16 | 1.383 (2) | C5—H5C | 0.9600 |
C21—H21 | 0.9300 | ||
C2—N3—O4 | 112.21 (11) | C13—C14—H14A | 109.8 |
C1—N6—N7 | 119.14 (11) | O15—C14—H14B | 109.8 |
C1—N6—H61 | 122.7 (10) | C13—C14—H14B | 109.8 |
N7—N6—H61 | 117.9 (10) | H14A—C14—H14B | 108.3 |
N6—N7—H71 | 106.7 (15) | C12—C13—C8 | 118.36 (15) |
N6—N7—H72 | 109.5 (16) | C12—C13—C14 | 119.56 (14) |
H71—N7—H72 | 108 (2) | C8—C13—C14 | 122.07 (13) |
C16—O15—C14 | 116.85 (12) | C11—C12—C13 | 121.52 (16) |
N3—O4—C5 | 108.33 (11) | C11—C12—H12 | 119.2 |
C18—C17—C16 | 117.83 (17) | C13—C12—H12 | 119.2 |
C18—C17—C22 | 121.37 (17) | C10—C11—C12 | 119.78 (15) |
C16—C17—C22 | 120.80 (16) | C10—C11—H11 | 120.1 |
C19—C18—C17 | 122.0 (2) | C12—C11—H11 | 120.1 |
C19—C18—H18 | 119.0 | C11—C10—C9 | 120.17 (17) |
C17—C18—H18 | 119.0 | C11—C10—H10 | 119.9 |
C18—C19—C20 | 119.6 (2) | C9—C10—H10 | 119.9 |
C18—C19—H19 | 120.2 | C10—C9—C8 | 120.50 (16) |
C20—C19—H19 | 120.2 | C10—C9—H9 | 119.7 |
C19—C20—C21 | 120.3 (2) | C8—C9—H9 | 119.7 |
C19—C20—H20 | 119.8 | C9—C8—C13 | 119.66 (13) |
C21—C20—H20 | 119.8 | C9—C8—C2 | 119.06 (13) |
C16—C21—C20 | 119.22 (18) | C13—C8—C2 | 121.27 (13) |
C16—C21—H21 | 120.4 | N3—C2—C8 | 125.28 (12) |
C20—C21—H21 | 120.4 | N3—C2—C1 | 115.94 (11) |
O15—C16—C21 | 124.22 (15) | C8—C2—C1 | 118.73 (11) |
O15—C16—C17 | 114.76 (14) | O4—C5—H5A | 109.5 |
C21—C16—C17 | 121.01 (16) | O4—C5—H5B | 109.5 |
C17—C22—H22A | 109.5 | H5A—C5—H5B | 109.5 |
C17—C22—H22B | 109.5 | O4—C5—H5C | 109.5 |
H22A—C22—H22B | 109.5 | H5A—C5—H5C | 109.5 |
C17—C22—H22C | 109.5 | H5B—C5—H5C | 109.5 |
H22A—C22—H22C | 109.5 | O1—C1—N6 | 124.57 (13) |
H22B—C22—H22C | 109.5 | O1—C1—C2 | 119.84 (12) |
O15—C14—C13 | 109.25 (12) | N6—C1—C2 | 115.59 (11) |
O15—C14—H14A | 109.8 | ||
C2—N3—O4—C5 | −174.13 (14) | C12—C11—C10—C9 | −0.5 (3) |
C16—C17—C18—C19 | 0.7 (3) | C11—C10—C9—C8 | −0.1 (2) |
C22—C17—C18—C19 | −179.34 (19) | C10—C9—C8—C13 | 0.7 (2) |
C17—C18—C19—C20 | −0.9 (3) | C10—C9—C8—C2 | −178.03 (13) |
C18—C19—C20—C21 | 0.1 (3) | C12—C13—C8—C9 | −0.6 (2) |
C19—C20—C21—C16 | 0.8 (3) | C14—C13—C8—C9 | −179.88 (13) |
C14—O15—C16—C21 | 10.5 (2) | C12—C13—C8—C2 | 178.12 (12) |
C14—O15—C16—C17 | −170.36 (13) | C14—C13—C8—C2 | −1.2 (2) |
C20—C21—C16—O15 | 178.15 (15) | O4—N3—C2—C8 | 1.5 (2) |
C20—C21—C16—C17 | −1.0 (2) | O4—N3—C2—C1 | 178.76 (11) |
C18—C17—C16—O15 | −178.97 (15) | C9—C8—C2—N3 | 96.60 (18) |
C22—C17—C16—O15 | 1.1 (2) | C13—C8—C2—N3 | −82.08 (18) |
C18—C17—C16—C21 | 0.2 (2) | C9—C8—C2—C1 | −80.61 (16) |
C22—C17—C16—C21 | −179.71 (17) | C13—C8—C2—C1 | 100.71 (15) |
C16—O15—C14—C13 | −176.27 (12) | N7—N6—C1—O1 | −4.0 (2) |
O15—C14—C13—C12 | 111.95 (15) | N7—N6—C1—C2 | 175.93 (13) |
O15—C14—C13—C8 | −68.73 (17) | N3—C2—C1—O1 | −170.98 (14) |
C8—C13—C12—C11 | −0.1 (2) | C8—C2—C1—O1 | 6.5 (2) |
C14—C13—C12—C11 | 179.25 (14) | N3—C2—C1—N6 | 9.09 (19) |
C13—C12—C11—C10 | 0.6 (3) | C8—C2—C1—N6 | −173.44 (13) |
Please define Cg |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H72···O1i | 0.86 (2) | 2.40 (2) | 3.220 (2) | 158 (2) |
N6—H61···N7ii | 0.87 (2) | 2.34 (1) | 3.191 (2) | 166 (1) |
C5—H5B···Cgiii | 0.96 | 2.69 | 3.461 (2) | 138 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1, z+1/2; (iii) −x+1/2, −y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H19N3O3 |
Mr | 313.35 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 21.4015 (6), 20.7277 (4), 7.6975 (2) |
β (°) | 109.103 (3) |
V (Å3) | 3226.60 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.3 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Sapphire3 |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.906, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 55120, 3174, 2532 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.105, 1.02 |
No. of reflections | 3174 |
No. of parameters | 222 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.17 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).
Please define Cg |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H72···O1i | 0.86 (2) | 2.40 (2) | 3.220 (2) | 158 (2) |
N6—H61···N7ii | 0.87 (2) | 2.34 (1) | 3.191 (2) | 166 (1) |
C5—H5B···Cgiii | 0.96 | 2.69 | 3.461 (2) | 137.90 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1, z+1/2; (iii) −x+1/2, −y+1/2, −z. |
Acknowledgements
RK acknowledges the Department of Science and Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Kresoxim-methyl is an active agrochemical (Chopra et al., 2004), strobilurin fungicide (Anke et al., 1977), with broad spectrum biological activity (Ypema, 1998; Ichinari et al., 1999; Grossmann & Retzlaff 1997). This type of compound is easily metabolized in nature as well as in living systems, and that is the reason studies on their fate in soil, plants and animal systems (Balba, 2007) are very important. Herein, we present the crystal structure of the title compound (I) which was synthesized from kresoxim-methyl.
In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related structure (Chopra et al., 2004). The dihedral angles formed by the two benzene rings (C8-C13/C16-C21) is 57.17 (5)°. In the crystal, molecules are connected by N—H···O and N—H···N hydrogen bonds into chains along [001] (Fig. 2). In addition a weak C—H···π interaction is observed.