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The title compound (also known as kresoxim-methyl), C18H19NO4, is an active agrochemical exhibiting fungicidal activity. The dihedral angle between the two rings is 65.9 (1)°. The crystal structure is stabilized by weak but highly directional C—H...O and C—H...π intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029848/ob6442sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029848/ob6442Isup2.hkl
Contains datablock I

CCDC reference: 259611

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.149
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C18 PLAT480_ALERT_4_C Long H...A H-Bond Reported H17B .. CG1 .. 2.81 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).

Methyl 2(E)-methoxyimino-2-[2-(2-methylphenoxymethyl)phenyl]acetate top
Crystal data top
C18H19NO4F(000) = 1328
Mr = 313.34Dx = 1.276 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 865 reflections
a = 16.843 (16) Åθ = 1.4–26.4°
b = 15.480 (14) ŵ = 0.09 mm1
c = 13.728 (13) ÅT = 293 K
β = 114.337 (14)°Block, colorless
V = 3261 (5) Å30.28 × 0.25 × 0.20 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3315 independent reflections
Radiation source: fine-focus sealed tube2332 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2120
Tmin = 0.933, Tmax = 0.982k = 1919
16747 measured reflectionsl = 1716
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0725P)2 + 1.85P]
where P = (Fo2 + 2Fc2)/3
3315 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
N10.83702 (10)0.12053 (10)0.36570 (12)0.0508 (4)
O10.67173 (8)0.02643 (8)0.13206 (10)0.0529 (4)
O20.82181 (10)0.06913 (9)0.43829 (11)0.0615 (4)
O30.87711 (14)0.20500 (10)0.22129 (14)0.0880 (6)
O40.87973 (10)0.07936 (8)0.14486 (11)0.0586 (4)
C10.50632 (15)0.16366 (13)0.05224 (18)0.0663 (6)
C20.44665 (16)0.16899 (15)0.0083 (2)0.0738 (7)
C30.46204 (15)0.12580 (15)0.0839 (2)0.0738 (7)
C40.53614 (13)0.07677 (14)0.13273 (18)0.0587 (5)
C50.59585 (12)0.07221 (11)0.08884 (15)0.0473 (4)
C60.58178 (14)0.11623 (12)0.00558 (16)0.0552 (5)
C70.64703 (19)0.11076 (19)0.0524 (2)0.0901 (9)
C80.68698 (12)0.02239 (12)0.22634 (14)0.0488 (4)
C90.77243 (12)0.06691 (11)0.25972 (13)0.0444 (4)
C100.84989 (12)0.02106 (11)0.29116 (13)0.0427 (4)
C110.92782 (14)0.06453 (13)0.32095 (16)0.0555 (5)
C120.92942 (17)0.15364 (14)0.32205 (19)0.0678 (6)
C130.85414 (17)0.19907 (13)0.29231 (18)0.0675 (6)
C140.77582 (15)0.15645 (12)0.26030 (16)0.0575 (5)
C150.85044 (11)0.07489 (11)0.29558 (14)0.0429 (4)
C160.80312 (18)0.12143 (16)0.5118 (2)0.0753 (7)
C170.89695 (17)0.12440 (14)0.06363 (18)0.0673 (6)
C180.86972 (12)0.12806 (11)0.21804 (15)0.0469 (4)
H10.49550.19300.11560.080*
H20.39630.20170.04130.089*
H30.42200.12940.11440.089*
H40.54570.04680.19530.070*
H7A0.62440.13850.12110.135*
H7B0.65900.05120.06050.135*
H7C0.69980.13900.00590.135*
H8A0.64090.06450.21210.059*
H8B0.68770.01560.28290.059*
H110.97950.03370.34040.067*
H120.98220.18270.34320.081*
H130.85550.25910.29360.081*
H140.72440.18810.23870.069*
H16A0.85300.15620.55240.113*
H16B0.78940.08500.55940.113*
H16C0.75430.15820.47310.113*
H17A0.85310.16770.03130.101*
H17B0.89610.08410.01010.101*
H17C0.95320.15140.09550.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0625 (10)0.0481 (8)0.0464 (9)0.0029 (7)0.0273 (8)0.0002 (7)
O10.0554 (8)0.0589 (8)0.0482 (7)0.0084 (6)0.0252 (6)0.0154 (6)
O20.0959 (11)0.0538 (8)0.0512 (8)0.0029 (7)0.0468 (8)0.0017 (6)
O30.1549 (17)0.0478 (9)0.0918 (12)0.0079 (9)0.0815 (12)0.0001 (8)
O40.0898 (11)0.0478 (7)0.0535 (8)0.0077 (7)0.0451 (8)0.0003 (6)
C10.0748 (15)0.0451 (11)0.0591 (13)0.0003 (10)0.0077 (12)0.0003 (9)
C20.0584 (14)0.0569 (13)0.0846 (17)0.0086 (10)0.0077 (13)0.0105 (12)
C30.0553 (13)0.0757 (15)0.0866 (17)0.0040 (11)0.0256 (12)0.0088 (13)
C40.0545 (12)0.0630 (12)0.0590 (12)0.0028 (10)0.0237 (10)0.0015 (10)
C50.0501 (11)0.0415 (9)0.0461 (10)0.0035 (8)0.0157 (9)0.0036 (8)
C60.0675 (13)0.0428 (10)0.0495 (11)0.0008 (9)0.0183 (10)0.0014 (8)
C70.117 (2)0.0943 (19)0.0761 (17)0.0280 (16)0.0575 (17)0.0365 (15)
C80.0545 (11)0.0518 (10)0.0422 (10)0.0048 (9)0.0221 (8)0.0043 (8)
C90.0597 (11)0.0419 (9)0.0363 (9)0.0001 (8)0.0244 (8)0.0048 (7)
C100.0574 (11)0.0404 (9)0.0360 (9)0.0035 (8)0.0250 (8)0.0051 (7)
C110.0604 (12)0.0578 (11)0.0556 (11)0.0095 (9)0.0312 (10)0.0105 (9)
C120.0854 (16)0.0591 (13)0.0706 (14)0.0270 (12)0.0439 (13)0.0188 (11)
C130.1070 (19)0.0404 (10)0.0676 (14)0.0160 (12)0.0485 (14)0.0140 (10)
C140.0833 (15)0.0443 (10)0.0501 (11)0.0068 (10)0.0328 (11)0.0040 (8)
C150.0457 (10)0.0423 (9)0.0420 (9)0.0002 (7)0.0194 (8)0.0011 (7)
C160.1017 (18)0.0796 (16)0.0623 (14)0.0032 (13)0.0518 (14)0.0151 (12)
C170.0966 (17)0.0629 (13)0.0563 (12)0.0128 (12)0.0454 (12)0.0029 (10)
C180.0558 (11)0.0404 (10)0.0473 (10)0.0008 (8)0.0242 (9)0.0008 (8)
Geometric parameters (Å, º) top
O1—C51.365 (2)C17—H17C0.9600
O1—C81.428 (2)C6—C11.376 (3)
O4—C181.321 (2)C6—C71.487 (3)
O4—C171.442 (2)C4—C31.376 (3)
O2—N11.379 (2)C4—H40.9300
O2—C161.427 (3)C14—C131.375 (3)
O3—C181.196 (2)C14—H140.9300
N1—C151.287 (2)C1—C21.371 (4)
C10—C111.379 (3)C1—H10.9300
C10—C91.389 (3)C12—C131.357 (3)
C10—C151.486 (3)C12—H120.9300
C9—C141.387 (3)C13—H130.9300
C9—C81.487 (3)C3—C21.359 (4)
C8—H8A0.9700C3—H30.9300
C8—H8B0.9700C16—H16A0.9600
C18—C151.484 (3)C16—H16B0.9600
C5—C41.371 (3)C16—H16C0.9600
C5—C61.396 (3)C2—H20.9300
C11—C121.380 (3)C7—H7A0.9600
C11—H110.9300C7—H7B0.9600
C17—H17A0.9600C7—H7C0.9600
C17—H17B0.9600
C5—O1—C8117.10 (14)C1—C6—C7122.3 (2)
C18—O4—C17116.18 (16)C5—C6—C7120.08 (19)
N1—O2—C16110.16 (16)C5—C4—C3119.8 (2)
C15—N1—O2111.46 (16)C5—C4—H4120.1
C11—C10—C9120.02 (18)C3—C4—H4120.1
C11—C10—C15119.11 (17)C13—C14—C9120.9 (2)
C9—C10—C15120.85 (16)C13—C14—H14119.6
C14—C9—C10118.54 (18)C9—C14—H14119.6
C14—C9—C8119.81 (18)C2—C1—C6122.1 (2)
C10—C9—C8121.65 (17)C2—C1—H1119.0
O1—C8—C9108.32 (15)C6—C1—H1119.0
O1—C8—H8A110.0C13—C12—C11120.2 (2)
C9—C8—H8A110.0C13—C12—H12119.9
O1—C8—H8B110.0C11—C12—H12119.9
C9—C8—H8B110.0C12—C13—C14120.1 (2)
H8A—C8—H8B108.4C12—C13—H13119.9
O3—C18—O4123.54 (18)C14—C13—H13119.9
O3—C18—C15125.15 (18)C2—C3—C4120.8 (2)
O4—C18—C15111.30 (16)C2—C3—H3119.6
N1—C15—C18112.96 (17)C4—C3—H3119.6
N1—C15—C10125.38 (16)O2—C16—H16A109.5
C18—C15—C10121.64 (15)O2—C16—H16B109.5
O1—C5—C4124.11 (18)H16A—C16—H16B109.5
O1—C5—C6115.31 (17)O2—C16—H16C109.5
C4—C5—C6120.58 (19)H16A—C16—H16C109.5
C10—C11—C12120.2 (2)H16B—C16—H16C109.5
C10—C11—H11119.9C3—C2—C1119.2 (2)
C12—C11—H11119.9C3—C2—H2120.4
O4—C17—H17A109.5C1—C2—H2120.4
O4—C17—H17B109.5C6—C7—H7A109.5
H17A—C17—H17B109.5C6—C7—H7B109.5
O4—C17—H17C109.5H7A—C7—H7B109.5
H17A—C17—H17C109.5C6—C7—H7C109.5
H17B—C17—H17C109.5H7A—C7—H7C109.5
C1—C6—C5117.6 (2)H7B—C7—H7C109.5
C16—O2—N1—C15177.27 (17)C8—O1—C5—C42.8 (3)
C11—C10—C9—C140.7 (3)C8—O1—C5—C6177.53 (16)
C15—C10—C9—C14177.94 (16)C9—C10—C11—C121.5 (3)
C11—C10—C9—C8179.60 (16)C15—C10—C11—C12177.15 (18)
C15—C10—C9—C81.8 (2)O1—C5—C6—C1179.77 (16)
C5—O1—C8—C9179.98 (14)C4—C5—C6—C10.1 (3)
C14—C9—C8—O1116.64 (18)O1—C5—C6—C70.4 (3)
C10—C9—C8—O163.6 (2)C4—C5—C6—C7180.0 (2)
C17—O4—C18—O32.6 (3)O1—C5—C4—C3179.01 (19)
C17—O4—C18—C15178.73 (17)C6—C5—C4—C30.6 (3)
O2—N1—C15—C18178.25 (15)C10—C9—C14—C130.7 (3)
O2—N1—C15—C100.1 (2)C8—C9—C14—C13179.05 (17)
O3—C18—C15—N13.8 (3)C5—C6—C1—C20.6 (3)
O4—C18—C15—N1177.52 (16)C7—C6—C1—C2179.5 (2)
O3—C18—C15—C10174.6 (2)C10—C11—C12—C131.0 (3)
O4—C18—C15—C104.1 (2)C11—C12—C13—C140.4 (3)
C11—C10—C15—N1106.6 (2)C9—C14—C13—C121.2 (3)
C9—C10—C15—N172.0 (2)C5—C4—C3—C20.9 (3)
C11—C10—C15—C1871.6 (2)C4—C3—C2—C10.4 (3)
C9—C10—C15—C18109.8 (2)C6—C1—C2—C30.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O20.972.523.191 (3)126
C17—H17B···Cg1i0.962.813.504 (4)130
C14—H14···O3ii0.932.603.440 (4)151
Symmetry codes: (i) x, y, z+1/2; (ii) x+3/2, y1/2, z+1/2.
 

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