organic compounds
N-[2-({[1-(4-Chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]-N-methoxyhydrazinecarboxamide
aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bNational Research Centre for Grapes, Pune 412 307, India
*Correspondence e-mail: rkvk.paper11@gmail.com
In the title compound, C18H18ClN5O3, the hydrazinecarboxamide N—N—C(O)—N unit is nearly planar [maximum deviation = 0.074 (2) Å] and is inclined at a dihedral angle of 57.43 (7)° with respect to the plane of the attached benzene ring. The chlorophenyl group makes dihedral angles of 19.71 (7) and 34.07 (6)° with the pyrazole and benzene rings, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules into inversion dimers that are further linked into chains along the a-axis direction by N—H⋯N hydrogen bonds. In addition, π–π stacking interactions are observed between benzene rings [centroid–centroid distance = 3.680 (1) Å].
Related literature
For the biological activity of pyraclostrobin (systematic name: methyl N-{2-[1-(4-chlorophenyl)-1H-pyrazol-3-yloxymethyl]phenyl}), see: Esteve-Turrillas et al. (2011); Mercader et al. (2008); Patel et al. (2012). For a related structure, see: Attia et al. (2012).
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/S1600536812038214/gk2517sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038214/gk2517Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812038214/gk2517Isup3.cml
Pyraclostrobin (0.373 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 70°C for 1 h. The reaction mixture was then cooled and compound was separated out by removal of the solvent under reduced pressure. The product was dissolved in methanol and kept for slow evaporation of solvent to get crystals of the title compound (m.p. 398 K).
The N-bound H atoms were located in a difference Fourier map and freely refined. All 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).
Pyraclostrobin, which belongs to the latest generation of strobilurin family of fungicides, shows a broad antifungal activity spectrum and higher efficiency and security profiles than previous fungicides (Patel et al., 2012; Esteve-Turrillas et al., 2011; Mercader et al., 2008).
In the title compound all bond lengths and angles are normal and correspond to those observed in the related structure (Attia et al., 2012). The hydrazinecarboxamide moiety (N2,N5,N6/O1/C1) is nearly planar with a maximum deviation of 0.074 (2) Å at atom N6, and is inclined at an angle of 57.43 (7)° with the benzene ring (C7–C12). The dihedral angle between the benzene rings is 34.07 (6)°. Chlorophenyl group makes a dihedral angle of 19.71 (7)° with the pyrazole ring. In the crystal, N6—H61···O1 hydrogen bonds link pairs of molecules to form inversion dimers and dimers are connected via N6—H62···N15 and N5—H51···N6 hydrogen bonds to form chains along the a axis of the π–π interactions between the benzene ring (C19—C24) of the molecule at (x, y, z) and the benzene ring of an inversion related molecule at (- x, 1 - y, -z)[centroid separation = 3.680 (1) Å, = 3.396 Å and centroid shift = 1.41 Å].
(Table 1, Fig. 2). The is further stabilized byFor the biological activity of pyraclostrobin (systematic name: methyl N-{2-[1-(4-chlorophenyl)-1H-pyrazol-3-yloxymethyl]phenyl}), see: Esteve-Turrillas et al. (2011); Mercader et al. (2008); Patel et al. (2012). For a related structure, see: Attia et al. (2012).
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).C18H18ClN5O3 | F(000) = 808 |
Mr = 387.82 | Dx = 1.403 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 14322 reflections |
a = 7.6830 (4) Å | θ = 3.5–28.0° |
b = 9.1597 (4) Å | µ = 0.24 mm−1 |
c = 26.1083 (12) Å | T = 293 K |
β = 91.683 (4)° | Plate, colourless |
V = 1836.55 (15) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 4 |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 3616 independent reflections |
Radiation source: fine-focus sealed tube | 2922 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 16.1049 pixels mm-1 | θmax = 26.0°, θmin = 3.5° |
ω scan | h = −9→9 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −11→11 |
Tmin = 0.832, Tmax = 1.000 | l = −32→32 |
27359 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0328P)2 + 1.1459P] where P = (Fo2 + 2Fc2)/3 |
3616 reflections | (Δ/σ)max < 0.001 |
256 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C18H18ClN5O3 | V = 1836.55 (15) Å3 |
Mr = 387.82 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.6830 (4) Å | µ = 0.24 mm−1 |
b = 9.1597 (4) Å | T = 293 K |
c = 26.1083 (12) Å | 0.3 × 0.2 × 0.2 mm |
β = 91.683 (4)° |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 3616 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 2922 reflections with I > 2σ(I) |
Tmin = 0.832, Tmax = 1.000 | Rint = 0.037 |
27359 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.21 e Å−3 |
3616 reflections | Δρmin = −0.23 e Å−3 |
256 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 | ||
Cl1 | 0.85943 (10) | 0.62565 (8) | 0.12909 (3) | 0.0738 (2) | |
C1 | 0.2793 (3) | −0.0901 (2) | −0.06670 (7) | 0.0343 (4) | |
O1 | 0.43612 (17) | −0.10159 (17) | −0.05818 (5) | 0.0413 (4) | |
N2 | 0.2112 (2) | −0.0929 (2) | −0.11646 (6) | 0.0417 (4) | |
O3 | 0.03330 (18) | −0.13060 (17) | −0.12029 (6) | 0.0459 (4) | |
C4 | −0.0602 (3) | −0.0201 (4) | −0.14807 (11) | 0.0706 (8) | |
H4B | −0.1812 | −0.0459 | −0.1506 | 0.106* | |
H4A | −0.0148 | −0.0116 | −0.1818 | 0.106* | |
H4C | −0.0474 | 0.0714 | −0.1305 | 0.106* | |
N5 | 0.1626 (2) | −0.0688 (2) | −0.03072 (6) | 0.0394 (4) | |
N6 | 0.2138 (2) | −0.0411 (2) | 0.02087 (7) | 0.0408 (4) | |
C7 | 0.3083 (3) | −0.1280 (2) | −0.16026 (8) | 0.0404 (5) | |
C8 | 0.2614 (3) | −0.2474 (3) | −0.19022 (9) | 0.0556 (6) | |
H8 | 0.1703 | −0.3074 | −0.1806 | 0.067* | |
C9 | 0.3496 (4) | −0.2774 (3) | −0.23418 (10) | 0.0668 (8) | |
H9 | 0.3177 | −0.3571 | −0.2544 | 0.080* | |
C10 | 0.4843 (4) | −0.1895 (4) | −0.24800 (9) | 0.0648 (8) | |
H10 | 0.5456 | −0.2110 | −0.2772 | 0.078* | |
C11 | 0.5297 (3) | −0.0690 (3) | −0.21873 (8) | 0.0534 (6) | |
H11 | 0.6205 | −0.0094 | −0.2289 | 0.064* | |
C12 | 0.4424 (3) | −0.0350 (3) | −0.17444 (7) | 0.0409 (5) | |
C13 | 0.4906 (3) | 0.0949 (3) | −0.14239 (8) | 0.0453 (5) | |
H131 | 0.3875 | 0.1335 | −0.1266 | 0.054* | |
H132 | 0.5729 | 0.0662 | −0.1154 | 0.054* | |
O13 | 0.5663 (2) | 0.2046 (2) | −0.17350 (6) | 0.0566 (4) | |
C14 | 0.6187 (3) | 0.3245 (3) | −0.14708 (9) | 0.0480 (6) | |
N15 | 0.6511 (2) | 0.3234 (2) | −0.09724 (7) | 0.0454 (4) | |
N16 | 0.7001 (2) | 0.4639 (2) | −0.08603 (7) | 0.0464 (5) | |
C17 | 0.6965 (4) | 0.5466 (3) | −0.12880 (11) | 0.0653 (7) | |
H17 | 0.7243 | 0.6453 | −0.1305 | 0.078* | |
C18 | 0.6457 (4) | 0.4619 (3) | −0.16864 (11) | 0.0636 (7) | |
H18 | 0.6318 | 0.4889 | −0.2029 | 0.076* | |
C19 | 0.7379 (3) | 0.5041 (2) | −0.03455 (9) | 0.0425 (5) | |
C20 | 0.6784 (3) | 0.4182 (2) | 0.00479 (9) | 0.0425 (5) | |
H20 | 0.6131 | 0.3349 | −0.0027 | 0.051* | |
C21 | 0.7157 (3) | 0.4559 (2) | 0.05512 (9) | 0.0464 (5) | |
H21 | 0.6777 | 0.3975 | 0.0817 | 0.056* | |
C22 | 0.8103 (3) | 0.5816 (3) | 0.06560 (10) | 0.0504 (6) | |
C23 | 0.8675 (3) | 0.6674 (3) | 0.02681 (11) | 0.0584 (7) | |
H23 | 0.9305 | 0.7517 | 0.0344 | 0.070* | |
C24 | 0.8325 (3) | 0.6298 (3) | −0.02355 (11) | 0.0548 (6) | |
H24 | 0.8720 | 0.6882 | −0.0499 | 0.066* | |
H61 | 0.305 (3) | 0.013 (3) | 0.0208 (8) | 0.045 (7)* | |
H62 | 0.251 (3) | −0.123 (3) | 0.0344 (10) | 0.053 (7)* | |
H51 | 0.053 (3) | −0.051 (3) | −0.0385 (9) | 0.051 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0739 (5) | 0.0668 (5) | 0.0798 (5) | −0.0013 (4) | −0.0113 (4) | −0.0195 (4) |
C1 | 0.0345 (11) | 0.0338 (10) | 0.0345 (10) | −0.0024 (8) | 0.0004 (8) | 0.0022 (8) |
O1 | 0.0298 (7) | 0.0558 (9) | 0.0381 (8) | 0.0005 (7) | −0.0013 (6) | 0.0025 (7) |
N2 | 0.0273 (8) | 0.0621 (12) | 0.0357 (9) | −0.0054 (8) | −0.0017 (7) | −0.0022 (8) |
O3 | 0.0298 (7) | 0.0595 (10) | 0.0481 (9) | −0.0076 (7) | −0.0048 (6) | 0.0012 (7) |
C4 | 0.0473 (15) | 0.100 (2) | 0.0640 (17) | 0.0128 (15) | −0.0123 (12) | 0.0124 (16) |
N5 | 0.0324 (9) | 0.0516 (11) | 0.0342 (9) | 0.0018 (8) | −0.0015 (7) | −0.0015 (8) |
N6 | 0.0385 (10) | 0.0487 (12) | 0.0350 (10) | −0.0009 (10) | −0.0010 (8) | −0.0004 (9) |
C7 | 0.0348 (11) | 0.0544 (13) | 0.0315 (10) | 0.0046 (10) | −0.0055 (8) | −0.0015 (9) |
C8 | 0.0558 (15) | 0.0615 (16) | 0.0491 (14) | −0.0044 (12) | −0.0036 (11) | −0.0096 (12) |
C9 | 0.0723 (18) | 0.0781 (19) | 0.0495 (15) | 0.0057 (16) | −0.0056 (13) | −0.0237 (14) |
C10 | 0.0602 (16) | 0.097 (2) | 0.0370 (13) | 0.0140 (16) | 0.0012 (11) | −0.0177 (14) |
C11 | 0.0413 (12) | 0.0837 (19) | 0.0352 (11) | 0.0048 (12) | −0.0002 (9) | −0.0012 (12) |
C12 | 0.0325 (10) | 0.0583 (13) | 0.0315 (10) | 0.0065 (10) | −0.0032 (8) | −0.0008 (10) |
C13 | 0.0417 (12) | 0.0565 (14) | 0.0379 (11) | −0.0034 (10) | 0.0058 (9) | 0.0032 (10) |
O13 | 0.0651 (11) | 0.0650 (11) | 0.0401 (9) | −0.0129 (9) | 0.0058 (8) | 0.0076 (8) |
C14 | 0.0415 (12) | 0.0543 (14) | 0.0486 (13) | 0.0016 (10) | 0.0084 (10) | 0.0117 (11) |
N15 | 0.0462 (11) | 0.0394 (10) | 0.0509 (11) | −0.0045 (8) | 0.0033 (8) | 0.0064 (8) |
N16 | 0.0448 (11) | 0.0346 (10) | 0.0603 (12) | 0.0004 (8) | 0.0084 (9) | 0.0097 (9) |
C17 | 0.0774 (19) | 0.0471 (15) | 0.0722 (18) | −0.0012 (13) | 0.0139 (15) | 0.0197 (14) |
C18 | 0.0702 (17) | 0.0653 (17) | 0.0558 (16) | 0.0017 (14) | 0.0075 (13) | 0.0215 (14) |
C19 | 0.0344 (11) | 0.0321 (11) | 0.0612 (14) | 0.0038 (9) | 0.0066 (10) | 0.0039 (10) |
C20 | 0.0354 (11) | 0.0301 (10) | 0.0623 (14) | 0.0002 (9) | 0.0062 (10) | −0.0001 (10) |
C21 | 0.0397 (12) | 0.0377 (12) | 0.0622 (15) | 0.0043 (10) | 0.0054 (10) | 0.0019 (11) |
C22 | 0.0400 (12) | 0.0404 (12) | 0.0708 (16) | 0.0064 (10) | 0.0005 (11) | −0.0076 (12) |
C23 | 0.0481 (14) | 0.0370 (13) | 0.090 (2) | −0.0070 (11) | 0.0034 (13) | −0.0050 (13) |
C24 | 0.0499 (14) | 0.0357 (12) | 0.0793 (18) | −0.0051 (11) | 0.0109 (12) | 0.0061 (12) |
Cl1—C22 | 1.737 (3) | C12—C13 | 1.495 (3) |
C1—O1 | 1.223 (2) | C13—O13 | 1.427 (3) |
C1—N5 | 1.332 (3) | C13—H131 | 0.9700 |
C1—N2 | 1.387 (2) | C13—H132 | 0.9700 |
N2—O3 | 1.411 (2) | O13—C14 | 1.352 (3) |
N2—C7 | 1.420 (3) | C14—N15 | 1.318 (3) |
O3—C4 | 1.427 (3) | C14—C18 | 1.397 (3) |
C4—H4B | 0.9600 | N15—N16 | 1.370 (3) |
C4—H4A | 0.9600 | N16—C17 | 1.349 (3) |
C4—H4C | 0.9600 | N16—C19 | 1.415 (3) |
N5—N6 | 1.415 (2) | C17—C18 | 1.346 (4) |
N5—H51 | 0.88 (2) | C17—H17 | 0.9300 |
N6—H61 | 0.86 (2) | C18—H18 | 0.9300 |
N6—H62 | 0.87 (3) | C19—C20 | 1.382 (3) |
C7—C8 | 1.386 (3) | C19—C24 | 1.387 (3) |
C7—C12 | 1.395 (3) | C20—C21 | 1.380 (3) |
C8—C9 | 1.378 (4) | C20—H20 | 0.9300 |
C8—H8 | 0.9300 | C21—C22 | 1.385 (3) |
C9—C10 | 1.368 (4) | C21—H21 | 0.9300 |
C9—H9 | 0.9300 | C22—C23 | 1.364 (4) |
C10—C11 | 1.382 (4) | C23—C24 | 1.378 (4) |
C10—H10 | 0.9300 | C23—H23 | 0.9300 |
C11—C12 | 1.389 (3) | C24—H24 | 0.9300 |
C11—H11 | 0.9300 | ||
O1—C1—N5 | 124.34 (18) | O13—C13—H131 | 109.7 |
O1—C1—N2 | 120.78 (18) | C12—C13—H131 | 109.7 |
N5—C1—N2 | 114.83 (17) | O13—C13—H132 | 109.7 |
C1—N2—O3 | 114.16 (16) | C12—C13—H132 | 109.7 |
C1—N2—C7 | 124.46 (16) | H131—C13—H132 | 108.2 |
O3—N2—C7 | 114.70 (15) | C14—O13—C13 | 113.70 (17) |
N2—O3—C4 | 109.54 (17) | N15—C14—O13 | 122.9 (2) |
O3—C4—H4B | 109.5 | N15—C14—C18 | 112.3 (2) |
O3—C4—H4A | 109.5 | O13—C14—C18 | 124.9 (2) |
H4B—C4—H4A | 109.5 | C14—N15—N16 | 104.28 (18) |
O3—C4—H4C | 109.5 | C17—N16—N15 | 110.6 (2) |
H4B—C4—H4C | 109.5 | C17—N16—C19 | 129.7 (2) |
H4A—C4—H4C | 109.5 | N15—N16—C19 | 119.64 (17) |
C1—N5—N6 | 121.57 (17) | C18—C17—N16 | 108.3 (2) |
C1—N5—H51 | 121.9 (15) | C18—C17—H17 | 125.8 |
N6—N5—H51 | 115.1 (15) | N16—C17—H17 | 125.8 |
N5—N6—H61 | 107.8 (15) | C17—C18—C14 | 104.5 (2) |
N5—N6—H62 | 108.1 (16) | C17—C18—H18 | 127.7 |
H61—N6—H62 | 104 (2) | C14—C18—H18 | 127.7 |
C8—C7—C12 | 120.9 (2) | C20—C19—C24 | 120.1 (2) |
C8—C7—N2 | 120.0 (2) | C20—C19—N16 | 119.6 (2) |
C12—C7—N2 | 119.00 (19) | C24—C19—N16 | 120.3 (2) |
C9—C8—C7 | 120.1 (2) | C21—C20—C19 | 120.1 (2) |
C9—C8—H8 | 120.0 | C21—C20—H20 | 120.0 |
C7—C8—H8 | 120.0 | C19—C20—H20 | 120.0 |
C10—C9—C8 | 119.8 (3) | C20—C21—C22 | 119.3 (2) |
C10—C9—H9 | 120.1 | C20—C21—H21 | 120.4 |
C8—C9—H9 | 120.1 | C22—C21—H21 | 120.4 |
C9—C10—C11 | 120.4 (2) | C23—C22—C21 | 120.7 (2) |
C9—C10—H10 | 119.8 | C23—C22—Cl1 | 120.6 (2) |
C11—C10—H10 | 119.8 | C21—C22—Cl1 | 118.7 (2) |
C10—C11—C12 | 121.2 (2) | C22—C23—C24 | 120.4 (2) |
C10—C11—H11 | 119.4 | C22—C23—H23 | 119.8 |
C12—C11—H11 | 119.4 | C24—C23—H23 | 119.8 |
C11—C12—C7 | 117.6 (2) | C23—C24—C19 | 119.4 (2) |
C11—C12—C13 | 121.8 (2) | C23—C24—H24 | 120.3 |
C7—C12—C13 | 120.64 (18) | C19—C24—H24 | 120.3 |
O13—C13—C12 | 109.90 (17) | ||
O1—C1—N2—O3 | 158.54 (18) | C13—O13—C14—N15 | 21.2 (3) |
N5—C1—N2—O3 | −23.9 (3) | C13—O13—C14—C18 | −159.2 (2) |
O1—C1—N2—C7 | 8.8 (3) | O13—C14—N15—N16 | 179.8 (2) |
N5—C1—N2—C7 | −173.6 (2) | C18—C14—N15—N16 | 0.1 (3) |
C1—N2—O3—C4 | 125.3 (2) | C14—N15—N16—C17 | 0.0 (2) |
C7—N2—O3—C4 | −81.9 (2) | C14—N15—N16—C19 | 177.28 (18) |
O1—C1—N5—N6 | 7.2 (3) | N15—N16—C17—C18 | −0.2 (3) |
N2—C1—N5—N6 | −170.22 (19) | C19—N16—C17—C18 | −177.1 (2) |
C1—N2—C7—C8 | 118.9 (2) | N16—C17—C18—C14 | 0.3 (3) |
O3—N2—C7—C8 | −30.7 (3) | N15—C14—C18—C17 | −0.2 (3) |
C1—N2—C7—C12 | −65.6 (3) | O13—C14—C18—C17 | −179.9 (2) |
O3—N2—C7—C12 | 144.89 (18) | C17—N16—C19—C20 | 157.9 (2) |
C12—C7—C8—C9 | 1.2 (4) | N15—N16—C19—C20 | −18.7 (3) |
N2—C7—C8—C9 | 176.6 (2) | C17—N16—C19—C24 | −21.4 (3) |
C7—C8—C9—C10 | 0.5 (4) | N15—N16—C19—C24 | 161.9 (2) |
C8—C9—C10—C11 | −1.5 (4) | C24—C19—C20—C21 | −1.2 (3) |
C9—C10—C11—C12 | 0.9 (4) | N16—C19—C20—C21 | 179.50 (19) |
C10—C11—C12—C7 | 0.6 (3) | C19—C20—C21—C22 | 1.2 (3) |
C10—C11—C12—C13 | 179.9 (2) | C20—C21—C22—C23 | −0.4 (3) |
C8—C7—C12—C11 | −1.7 (3) | C20—C21—C22—Cl1 | −178.87 (16) |
N2—C7—C12—C11 | −177.21 (19) | C21—C22—C23—C24 | −0.3 (4) |
C8—C7—C12—C13 | 179.1 (2) | Cl1—C22—C23—C24 | 178.14 (19) |
N2—C7—C12—C13 | 3.6 (3) | C22—C23—C24—C19 | 0.2 (4) |
C11—C12—C13—O13 | 27.3 (3) | C20—C19—C24—C23 | 0.5 (3) |
C7—C12—C13—O13 | −153.51 (19) | N16—C19—C24—C23 | 179.8 (2) |
C12—C13—O13—C14 | −178.05 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H51···N6i | 0.88 (2) | 2.28 (2) | 3.080 (3) | 153 (2) |
N6—H61···O1ii | 0.86 (2) | 2.34 (2) | 3.120 (3) | 152 (2) |
N6—H62···N15ii | 0.87 (3) | 2.56 (3) | 3.408 (3) | 164 (2) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H18ClN5O3 |
Mr | 387.82 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 7.6830 (4), 9.1597 (4), 26.1083 (12) |
β (°) | 91.683 (4) |
V (Å3) | 1836.55 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
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 | 0.832, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27359, 3616, 2922 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.112, 1.12 |
No. of reflections | 3616 |
No. of parameters | 256 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.23 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H51···N6i | 0.88 (2) | 2.28 (2) | 3.080 (3) | 153 (2) |
N6—H61···O1ii | 0.86 (2) | 2.34 (2) | 3.120 (3) | 152 (2) |
N6—H62···N15ii | 0.87 (3) | 2.56 (3) | 3.408 (3) | 164 (2) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z. |
Acknowledgements
RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.
References
Attia, M. I., Ghabbour, H. A., El-Azzouny, A. A., Quah, C. K. & Fun, H.-K. (2012). Acta Cryst. E68, o671. CSD CrossRef IUCr Journals Google Scholar
Esteve-Turrillas, F. A., Mercader, J. V., Agulló, C., Abad-Somovilla, A. & Abad-Fuentes, A. (2011). J. Chromatogr. A, 30, 4902–4909. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Mercader, J. V., Suárez-Pantaleón, C., Agulló, C., Abad-Somovilla, A. & Abad-Fuentes, A. (2008). J. Agric. Food Chem. 56, 7682–7690. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Patel, J. S., Gudmestad, N. C., Meinhardt, S. & Adhikari, T. B. (2012). Crop Prot. 34, 37–41. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
Pyraclostrobin, which belongs to the latest generation of strobilurin family of fungicides, shows a broad antifungal activity spectrum and higher efficiency and security profiles than previous fungicides (Patel et al., 2012; Esteve-Turrillas et al., 2011; Mercader et al., 2008).
In the title compound all bond lengths and angles are normal and correspond to those observed in the related structure (Attia et al., 2012). The hydrazinecarboxamide moiety (N2,N5,N6/O1/C1) is nearly planar with a maximum deviation of 0.074 (2) Å at atom N6, and is inclined at an angle of 57.43 (7)° with the benzene ring (C7–C12). The dihedral angle between the benzene rings is 34.07 (6)°. Chlorophenyl group makes a dihedral angle of 19.71 (7)° with the pyrazole ring. In the crystal, N6—H61···O1 hydrogen bonds link pairs of molecules to form inversion dimers and dimers are connected via N6—H62···N15 and N5—H51···N6 hydrogen bonds to form chains along the a axis of the unit cell (Table 1, Fig. 2). The crystal structure is further stabilized by π–π interactions between the benzene ring (C19—C24) of the molecule at (x, y, z) and the benzene ring of an inversion related molecule at (- x, 1 - y, -z)[centroid separation = 3.680 (1) Å, interplanar spacing = 3.396 Å and centroid shift = 1.41 Å].