The title compound (also known as kresoxim-methyl), C
18H
19NO
4, 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
CCDC reference: 259611
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C18H19NO4 | F(000) = 1328 |
Mr = 313.34 | Dx = 1.276 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 865 reflections |
a = 16.843 (16) Å | θ = 1.4–26.4° |
b = 15.480 (14) Å | µ = 0.09 mm−1 |
c = 13.728 (13) Å | T = 293 K |
β = 114.337 (14)° | Block, colorless |
V = 3261 (5) Å3 | 0.28 × 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 tube | 2332 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→20 |
Tmin = 0.933, Tmax = 0.982 | k = −19→19 |
16747 measured reflections | l = −17→16 |
Refinement top
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-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 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.83702 (10) | 0.12053 (10) | 0.36570 (12) | 0.0508 (4) | |
O1 | 0.67173 (8) | 0.02643 (8) | 0.13206 (10) | 0.0529 (4) | |
O2 | 0.82181 (10) | 0.06913 (9) | 0.43829 (11) | 0.0615 (4) | |
O3 | 0.87711 (14) | 0.20500 (10) | 0.22129 (14) | 0.0880 (6) | |
O4 | 0.87973 (10) | 0.07936 (8) | 0.14486 (11) | 0.0586 (4) | |
C1 | 0.50632 (15) | 0.16366 (13) | −0.05224 (18) | 0.0663 (6) | |
C2 | 0.44665 (16) | 0.16899 (15) | −0.0083 (2) | 0.0738 (7) | |
C3 | 0.46204 (15) | 0.12580 (15) | 0.0839 (2) | 0.0738 (7) | |
C4 | 0.53614 (13) | 0.07677 (14) | 0.13273 (18) | 0.0587 (5) | |
C5 | 0.59585 (12) | 0.07221 (11) | 0.08884 (15) | 0.0473 (4) | |
C6 | 0.58178 (14) | 0.11623 (12) | −0.00558 (16) | 0.0552 (5) | |
C7 | 0.64703 (19) | 0.11076 (19) | −0.0524 (2) | 0.0901 (9) | |
C8 | 0.68698 (12) | −0.02239 (12) | 0.22634 (14) | 0.0488 (4) | |
C9 | 0.77243 (12) | −0.06691 (11) | 0.25972 (13) | 0.0444 (4) | |
C10 | 0.84989 (12) | −0.02106 (11) | 0.29116 (13) | 0.0427 (4) | |
C11 | 0.92782 (14) | −0.06453 (13) | 0.32095 (16) | 0.0555 (5) | |
C12 | 0.92942 (17) | −0.15364 (14) | 0.32205 (19) | 0.0678 (6) | |
C13 | 0.85414 (17) | −0.19907 (13) | 0.29231 (18) | 0.0675 (6) | |
C14 | 0.77582 (15) | −0.15645 (12) | 0.26030 (16) | 0.0575 (5) | |
C15 | 0.85044 (11) | 0.07489 (11) | 0.29558 (14) | 0.0429 (4) | |
C16 | 0.80312 (18) | 0.12143 (16) | 0.5118 (2) | 0.0753 (7) | |
C17 | 0.89695 (17) | 0.12440 (14) | 0.06363 (18) | 0.0673 (6) | |
C18 | 0.86972 (12) | 0.12806 (11) | 0.21804 (15) | 0.0469 (4) | |
H1 | 0.4955 | 0.1930 | −0.1156 | 0.080* | |
H2 | 0.3963 | 0.2017 | −0.0413 | 0.089* | |
H3 | 0.4220 | 0.1294 | 0.1144 | 0.089* | |
H4 | 0.5457 | 0.0468 | 0.1953 | 0.070* | |
H7A | 0.6244 | 0.1385 | −0.1211 | 0.135* | |
H7B | 0.6590 | 0.0512 | −0.0605 | 0.135* | |
H7C | 0.6998 | 0.1390 | −0.0059 | 0.135* | |
H8A | 0.6409 | −0.0645 | 0.2121 | 0.059* | |
H8B | 0.6877 | 0.0156 | 0.2829 | 0.059* | |
H11 | 0.9795 | −0.0337 | 0.3404 | 0.067* | |
H12 | 0.9822 | −0.1827 | 0.3432 | 0.081* | |
H13 | 0.8555 | −0.2591 | 0.2936 | 0.081* | |
H14 | 0.7244 | −0.1881 | 0.2387 | 0.069* | |
H16A | 0.8530 | 0.1562 | 0.5524 | 0.113* | |
H16B | 0.7894 | 0.0850 | 0.5594 | 0.113* | |
H16C | 0.7543 | 0.1582 | 0.4731 | 0.113* | |
H17A | 0.8531 | 0.1677 | 0.0313 | 0.101* | |
H17B | 0.8961 | 0.0841 | 0.0101 | 0.101* | |
H17C | 0.9532 | 0.1514 | 0.0955 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0625 (10) | 0.0481 (8) | 0.0464 (9) | −0.0029 (7) | 0.0273 (8) | −0.0002 (7) |
O1 | 0.0554 (8) | 0.0589 (8) | 0.0482 (7) | 0.0084 (6) | 0.0252 (6) | 0.0154 (6) |
O2 | 0.0959 (11) | 0.0538 (8) | 0.0512 (8) | −0.0029 (7) | 0.0468 (8) | −0.0017 (6) |
O3 | 0.1549 (17) | 0.0478 (9) | 0.0918 (12) | −0.0079 (9) | 0.0815 (12) | −0.0001 (8) |
O4 | 0.0898 (11) | 0.0478 (7) | 0.0535 (8) | −0.0077 (7) | 0.0451 (8) | −0.0003 (6) |
C1 | 0.0748 (15) | 0.0451 (11) | 0.0591 (13) | 0.0003 (10) | 0.0077 (12) | −0.0003 (9) |
C2 | 0.0584 (14) | 0.0569 (13) | 0.0846 (17) | 0.0086 (10) | 0.0077 (13) | −0.0105 (12) |
C3 | 0.0553 (13) | 0.0757 (15) | 0.0866 (17) | 0.0040 (11) | 0.0256 (12) | −0.0088 (13) |
C4 | 0.0545 (12) | 0.0630 (12) | 0.0590 (12) | −0.0028 (10) | 0.0237 (10) | −0.0015 (10) |
C5 | 0.0501 (11) | 0.0415 (9) | 0.0461 (10) | −0.0035 (8) | 0.0157 (9) | −0.0036 (8) |
C6 | 0.0675 (13) | 0.0428 (10) | 0.0495 (11) | 0.0008 (9) | 0.0183 (10) | 0.0014 (8) |
C7 | 0.117 (2) | 0.0943 (19) | 0.0761 (17) | 0.0280 (16) | 0.0575 (17) | 0.0365 (15) |
C8 | 0.0545 (11) | 0.0518 (10) | 0.0422 (10) | −0.0048 (9) | 0.0221 (8) | 0.0043 (8) |
C9 | 0.0597 (11) | 0.0419 (9) | 0.0363 (9) | −0.0001 (8) | 0.0244 (8) | 0.0048 (7) |
C10 | 0.0574 (11) | 0.0404 (9) | 0.0360 (9) | 0.0035 (8) | 0.0250 (8) | 0.0051 (7) |
C11 | 0.0604 (12) | 0.0578 (11) | 0.0556 (11) | 0.0095 (9) | 0.0312 (10) | 0.0105 (9) |
C12 | 0.0854 (16) | 0.0591 (13) | 0.0706 (14) | 0.0270 (12) | 0.0439 (13) | 0.0188 (11) |
C13 | 0.1070 (19) | 0.0404 (10) | 0.0676 (14) | 0.0160 (12) | 0.0485 (14) | 0.0140 (10) |
C14 | 0.0833 (15) | 0.0443 (10) | 0.0501 (11) | −0.0068 (10) | 0.0328 (11) | 0.0040 (8) |
C15 | 0.0457 (10) | 0.0423 (9) | 0.0420 (9) | −0.0002 (7) | 0.0194 (8) | 0.0011 (7) |
C16 | 0.1017 (18) | 0.0796 (16) | 0.0623 (14) | −0.0032 (13) | 0.0518 (14) | −0.0151 (12) |
C17 | 0.0966 (17) | 0.0629 (13) | 0.0563 (12) | −0.0128 (12) | 0.0454 (12) | 0.0029 (10) |
C18 | 0.0558 (11) | 0.0404 (10) | 0.0473 (10) | −0.0008 (8) | 0.0242 (9) | 0.0008 (8) |
Geometric parameters (Å, º) top
O1—C5 | 1.365 (2) | C17—H17C | 0.9600 |
O1—C8 | 1.428 (2) | C6—C1 | 1.376 (3) |
O4—C18 | 1.321 (2) | C6—C7 | 1.487 (3) |
O4—C17 | 1.442 (2) | C4—C3 | 1.376 (3) |
O2—N1 | 1.379 (2) | C4—H4 | 0.9300 |
O2—C16 | 1.427 (3) | C14—C13 | 1.375 (3) |
O3—C18 | 1.196 (2) | C14—H14 | 0.9300 |
N1—C15 | 1.287 (2) | C1—C2 | 1.371 (4) |
C10—C11 | 1.379 (3) | C1—H1 | 0.9300 |
C10—C9 | 1.389 (3) | C12—C13 | 1.357 (3) |
C10—C15 | 1.486 (3) | C12—H12 | 0.9300 |
C9—C14 | 1.387 (3) | C13—H13 | 0.9300 |
C9—C8 | 1.487 (3) | C3—C2 | 1.359 (4) |
C8—H8A | 0.9700 | C3—H3 | 0.9300 |
C8—H8B | 0.9700 | C16—H16A | 0.9600 |
C18—C15 | 1.484 (3) | C16—H16B | 0.9600 |
C5—C4 | 1.371 (3) | C16—H16C | 0.9600 |
C5—C6 | 1.396 (3) | C2—H2 | 0.9300 |
C11—C12 | 1.380 (3) | C7—H7A | 0.9600 |
C11—H11 | 0.9300 | C7—H7B | 0.9600 |
C17—H17A | 0.9600 | C7—H7C | 0.9600 |
C17—H17B | 0.9600 | | |
| | | |
C5—O1—C8 | 117.10 (14) | C1—C6—C7 | 122.3 (2) |
C18—O4—C17 | 116.18 (16) | C5—C6—C7 | 120.08 (19) |
N1—O2—C16 | 110.16 (16) | C5—C4—C3 | 119.8 (2) |
C15—N1—O2 | 111.46 (16) | C5—C4—H4 | 120.1 |
C11—C10—C9 | 120.02 (18) | C3—C4—H4 | 120.1 |
C11—C10—C15 | 119.11 (17) | C13—C14—C9 | 120.9 (2) |
C9—C10—C15 | 120.85 (16) | C13—C14—H14 | 119.6 |
C14—C9—C10 | 118.54 (18) | C9—C14—H14 | 119.6 |
C14—C9—C8 | 119.81 (18) | C2—C1—C6 | 122.1 (2) |
C10—C9—C8 | 121.65 (17) | C2—C1—H1 | 119.0 |
O1—C8—C9 | 108.32 (15) | C6—C1—H1 | 119.0 |
O1—C8—H8A | 110.0 | C13—C12—C11 | 120.2 (2) |
C9—C8—H8A | 110.0 | C13—C12—H12 | 119.9 |
O1—C8—H8B | 110.0 | C11—C12—H12 | 119.9 |
C9—C8—H8B | 110.0 | C12—C13—C14 | 120.1 (2) |
H8A—C8—H8B | 108.4 | C12—C13—H13 | 119.9 |
O3—C18—O4 | 123.54 (18) | C14—C13—H13 | 119.9 |
O3—C18—C15 | 125.15 (18) | C2—C3—C4 | 120.8 (2) |
O4—C18—C15 | 111.30 (16) | C2—C3—H3 | 119.6 |
N1—C15—C18 | 112.96 (17) | C4—C3—H3 | 119.6 |
N1—C15—C10 | 125.38 (16) | O2—C16—H16A | 109.5 |
C18—C15—C10 | 121.64 (15) | O2—C16—H16B | 109.5 |
O1—C5—C4 | 124.11 (18) | H16A—C16—H16B | 109.5 |
O1—C5—C6 | 115.31 (17) | O2—C16—H16C | 109.5 |
C4—C5—C6 | 120.58 (19) | H16A—C16—H16C | 109.5 |
C10—C11—C12 | 120.2 (2) | H16B—C16—H16C | 109.5 |
C10—C11—H11 | 119.9 | C3—C2—C1 | 119.2 (2) |
C12—C11—H11 | 119.9 | C3—C2—H2 | 120.4 |
O4—C17—H17A | 109.5 | C1—C2—H2 | 120.4 |
O4—C17—H17B | 109.5 | C6—C7—H7A | 109.5 |
H17A—C17—H17B | 109.5 | C6—C7—H7B | 109.5 |
O4—C17—H17C | 109.5 | H7A—C7—H7B | 109.5 |
H17A—C17—H17C | 109.5 | C6—C7—H7C | 109.5 |
H17B—C17—H17C | 109.5 | H7A—C7—H7C | 109.5 |
C1—C6—C5 | 117.6 (2) | H7B—C7—H7C | 109.5 |
| | | |
C16—O2—N1—C15 | −177.27 (17) | C8—O1—C5—C4 | 2.8 (3) |
C11—C10—C9—C14 | 0.7 (3) | C8—O1—C5—C6 | −177.53 (16) |
C15—C10—C9—C14 | −177.94 (16) | C9—C10—C11—C12 | −1.5 (3) |
C11—C10—C9—C8 | −179.60 (16) | C15—C10—C11—C12 | 177.15 (18) |
C15—C10—C9—C8 | 1.8 (2) | O1—C5—C6—C1 | −179.77 (16) |
C5—O1—C8—C9 | 179.98 (14) | C4—C5—C6—C1 | −0.1 (3) |
C14—C9—C8—O1 | −116.64 (18) | O1—C5—C6—C7 | 0.4 (3) |
C10—C9—C8—O1 | 63.6 (2) | C4—C5—C6—C7 | −180.0 (2) |
C17—O4—C18—O3 | −2.6 (3) | O1—C5—C4—C3 | 179.01 (19) |
C17—O4—C18—C15 | 178.73 (17) | C6—C5—C4—C3 | −0.6 (3) |
O2—N1—C15—C18 | −178.25 (15) | C10—C9—C14—C13 | 0.7 (3) |
O2—N1—C15—C10 | 0.1 (2) | C8—C9—C14—C13 | −179.05 (17) |
O3—C18—C15—N1 | 3.8 (3) | C5—C6—C1—C2 | 0.6 (3) |
O4—C18—C15—N1 | −177.52 (16) | C7—C6—C1—C2 | −179.5 (2) |
O3—C18—C15—C10 | −174.6 (2) | C10—C11—C12—C13 | 1.0 (3) |
O4—C18—C15—C10 | 4.1 (2) | C11—C12—C13—C14 | 0.4 (3) |
C11—C10—C15—N1 | −106.6 (2) | C9—C14—C13—C12 | −1.2 (3) |
C9—C10—C15—N1 | 72.0 (2) | C5—C4—C3—C2 | 0.9 (3) |
C11—C10—C15—C18 | 71.6 (2) | C4—C3—C2—C1 | −0.4 (3) |
C9—C10—C15—C18 | −109.8 (2) | C6—C1—C2—C3 | −0.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O2 | 0.97 | 2.52 | 3.191 (3) | 126 |
C17—H17B···Cg1i | 0.96 | 2.81 | 3.504 (4) | 130 |
C14—H14···O3ii | 0.93 | 2.60 | 3.440 (4) | 151 |
Symmetry codes: (i) x, −y, z+1/2; (ii) −x+3/2, y−1/2, −z+1/2. |