Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044145/im2031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044145/im2031Isup2.hkl |
CCDC reference: 663764
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.057
- wR factor = 0.124
- Data-to-parameter ratio = 8.4
checkCIF/PLATON results
No syntax errors found
Alert level C STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.15 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.38 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18' PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C15 - C16 ... 1.43 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 31 C7 -C15 -C16 -N2 94.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 32 C17 -C15 -C16 -N2 -80.00 7.00 1.555 1.555 1.555 1.555 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 10.00
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 2109 Count of symmetry unique reflns 2112 Completeness (_total/calc) 99.86% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Several novel acrylate compounds are useful as inhibitors of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al., 2004; Creagh & Hubbell, 1992; Ibers & Hamilton, 1964).
To a solution of (Z)-ethyl 3-amino-2-cyano-3-(4-fluorophenyl)acrylate (1.17 g,0.0050 mol) in CH2Cl2 (18 ml), benzoyl chloride (2.11 g,0.015 mol) was added. Subsequently, Et3N (1.52 g,0.015 mol) was dropped into the solution under stirring. The reaction mixture was then heated to reflux and stirred for 4 h. Subsequently, it was cooled to room temperature, the reaction solution was filtered off and some white solid was separated. The organic phase was washed with water and then dried over Na2SO4. After removal of the solvent, a brown dope was obtained. After column chromatography using ethyl acetate/light petroleum (1:6) as the eluent, the pure E-isomer is separated from the mother liquid as colorless prismatic crystals. Small single crystals were grown from a solution of ethyl acetate/light petroleum (3:1) after 45 days, at room temperature.
The position of H1 was determined from the difference Fourier map and was refined without constraints. Methyl H atoms were placed in calculated positions with C—H=0.96 Å and the torsion angle was refined to fit the electron density; thermal parameters were refined as Uiso(H)=1.5Ueq(C). Other H atoms were placed in calculated positions with C—H = 0.96 Å (methylene) and 0.93 Å (aromatic C—H), and refined using a riding model, with Uiso(H)=1.2Ueq(C). In the absence of significant anomalous scattering, Friedel pairs were merged.
The title compound is useful as an inhibitor of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al. 2004; Creagh & Hubbell, 1992; Ibers & Hamilton, 1964). Recently, we obtained single crystals of this compound, and its crystal structure is reported here. The molecular conformation is stabilized by intramolecular C—H···O and N—H···O hydrogen bonds (Table 1). The crystal packing is governed by additional C—H···N and C—H···O interactions.
Several novel acrylate compounds are useful as inhibitors of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al., 2004; Creagh & Hubbell, 1992; Ibers & Hamilton, 1964).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C19H15FN2O3 | F(000) = 704 |
Mr = 338.33 | Dx = 1.343 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P2ac2ab | Cell parameters from 2229 reflections |
a = 6.2149 (5) Å | θ = 2.6–21.4° |
b = 14.138 (1) Å | µ = 0.10 mm−1 |
c = 19.050 (1) Å | T = 292 K |
V = 1673.8 (2) Å3 | Needle, colorless |
Z = 4 | 0.20 × 0.10 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 1634 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 27.0°, θmin = 1.8° |
phi and ω scans | h = −7→7 |
15612 measured reflections | k = −14→18 |
2109 independent reflections | l = −24→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0453P)2 + 0.3759P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
2109 reflections | Δρmax = 0.17 e Å−3 |
250 parameters | Δρmin = −0.17 e Å−3 |
4 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
C19H15FN2O3 | V = 1673.8 (2) Å3 |
Mr = 338.33 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.2149 (5) Å | µ = 0.10 mm−1 |
b = 14.138 (1) Å | T = 292 K |
c = 19.050 (1) Å | 0.20 × 0.10 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 1634 reflections with I > 2σ(I) |
15612 measured reflections | Rint = 0.052 |
2109 independent reflections |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.124 | Δρmax = 0.17 e Å−3 |
S = 1.11 | Δρmin = −0.17 e Å−3 |
2109 reflections | Absolute structure: Flack (1983) |
250 parameters | Absolute structure parameter: 0 (10) |
4 restraints |
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 | Occ. (<1) | |
C1 | 0.5735 (7) | 0.8275 (3) | 0.24083 (18) | 0.0574 (10) | |
C2 | 0.7450 (7) | 0.8137 (2) | 0.19792 (18) | 0.0548 (9) | |
H2 | 0.8569 | 0.8574 | 0.1961 | 0.066* | |
C3 | 0.7488 (6) | 0.7328 (2) | 0.15683 (17) | 0.0480 (8) | |
H3 | 0.8650 | 0.7216 | 0.1272 | 0.058* | |
C4 | 0.5810 (5) | 0.6683 (2) | 0.15954 (14) | 0.0412 (7) | |
C5 | 0.4083 (6) | 0.6857 (3) | 0.20415 (17) | 0.0587 (10) | |
H5 | 0.2945 | 0.6431 | 0.2062 | 0.070* | |
C6 | 0.4053 (7) | 0.7653 (3) | 0.24518 (19) | 0.0664 (11) | |
H6 | 0.2909 | 0.7768 | 0.2755 | 0.080* | |
C7 | 0.5925 (6) | 0.5794 (2) | 0.11847 (15) | 0.0433 (8) | |
C8 | 0.2774 (6) | 0.6138 (3) | 0.04035 (17) | 0.0533 (9) | |
C9 | 0.1542 (6) | 0.5683 (3) | −0.01794 (16) | 0.0508 (9) | |
C10 | 0.2301 (8) | 0.4928 (3) | −0.05696 (19) | 0.0707 (11) | |
H10 | 0.3628 | 0.4659 | −0.0464 | 0.085* | |
C11 | 0.1081 (9) | 0.4574 (3) | −0.1117 (2) | 0.0879 (15) | |
H11 | 0.1609 | 0.4077 | −0.1387 | 0.106* | |
C12 | −0.0893 (9) | 0.4948 (4) | −0.1265 (2) | 0.0926 (18) | |
H12 | −0.1738 | 0.4691 | −0.1620 | 0.111* | |
C13 | −0.1612 (8) | 0.5702 (4) | −0.0887 (2) | 0.0806 (14) | |
H13 | −0.2938 | 0.5969 | −0.0997 | 0.097* | |
C14 | −0.0433 (6) | 0.6077 (3) | −0.03491 (19) | 0.0640 (11) | |
H14 | −0.0952 | 0.6594 | −0.0099 | 0.077* | |
C15 | 0.7524 (6) | 0.5153 (2) | 0.13150 (15) | 0.0459 (8) | |
C16 | 0.8881 (6) | 0.5289 (2) | 0.19117 (18) | 0.0472 (8) | |
C17 | 0.7806 (7) | 0.4278 (3) | 0.09120 (18) | 0.0570 (10) | |
C18 | 0.976 (2) | 0.2890 (7) | 0.0723 (5) | 0.072 (3) | 0.75 (2) |
H18A | 1.0026 | 0.3004 | 0.0228 | 0.087* | 0.75 (2) |
H18B | 0.8489 | 0.2499 | 0.0770 | 0.087* | 0.75 (2) |
C19 | 1.1684 (18) | 0.2416 (9) | 0.1059 (6) | 0.087 (4) | 0.75 (2) |
H19A | 1.2945 | 0.2795 | 0.0984 | 0.131* | 0.75 (2) |
H19B | 1.1893 | 0.1803 | 0.0853 | 0.131* | 0.75 (2) |
H19C | 1.1435 | 0.2348 | 0.1554 | 0.131* | 0.75 (2) |
C18' | 1.081 (6) | 0.3096 (18) | 0.0732 (17) | 0.084 (10) | 0.25 (2) |
H18C | 1.2306 | 0.3285 | 0.0735 | 0.101* | 0.25 (2) |
H18D | 1.0332 | 0.3045 | 0.0248 | 0.101* | 0.25 (2) |
C19' | 1.053 (9) | 0.214 (2) | 0.111 (2) | 0.131 (14) | 0.25 (2) |
H19D | 1.1194 | 0.2175 | 0.1565 | 0.196* | 0.25 (2) |
H19E | 1.1203 | 0.1652 | 0.0839 | 0.196* | 0.25 (2) |
H19F | 0.9027 | 0.2005 | 0.1162 | 0.196* | 0.25 (2) |
F1 | 0.5689 (5) | 0.90628 (18) | 0.28136 (12) | 0.0907 (9) | |
N1 | 0.4415 (5) | 0.5588 (2) | 0.06813 (15) | 0.0554 (8) | |
H1 | 0.471 (6) | 0.503 (3) | 0.0484 (19) | 0.066* | |
N2 | 0.9903 (6) | 0.5370 (2) | 0.24060 (17) | 0.0661 (9) | |
O1 | 0.2334 (5) | 0.69149 (19) | 0.06227 (14) | 0.0737 (8) | |
O2 | 0.6578 (5) | 0.39995 (18) | 0.04527 (14) | 0.0725 (8) | |
O3 | 0.9497 (5) | 0.3796 (2) | 0.11071 (14) | 0.0772 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.068 (3) | 0.051 (2) | 0.0531 (18) | 0.012 (2) | 0.000 (2) | −0.0122 (17) |
C2 | 0.061 (2) | 0.0410 (19) | 0.062 (2) | −0.004 (2) | −0.004 (2) | −0.0069 (17) |
C3 | 0.0492 (19) | 0.0437 (19) | 0.0510 (17) | −0.0010 (19) | 0.0071 (17) | −0.0026 (15) |
C4 | 0.0406 (18) | 0.0435 (18) | 0.0396 (14) | 0.0007 (17) | 0.0026 (15) | 0.0003 (13) |
C5 | 0.049 (2) | 0.067 (3) | 0.0600 (19) | −0.014 (2) | 0.0106 (18) | −0.0049 (19) |
C6 | 0.054 (2) | 0.086 (3) | 0.059 (2) | 0.007 (3) | 0.017 (2) | −0.017 (2) |
C7 | 0.0448 (18) | 0.0430 (18) | 0.0423 (15) | −0.0059 (17) | 0.0085 (15) | 0.0009 (14) |
C8 | 0.056 (2) | 0.051 (2) | 0.0532 (18) | −0.004 (2) | 0.0010 (18) | 0.0007 (17) |
C9 | 0.055 (2) | 0.054 (2) | 0.0434 (16) | −0.0096 (19) | −0.0018 (16) | 0.0066 (16) |
C10 | 0.090 (3) | 0.060 (2) | 0.063 (2) | −0.003 (3) | −0.013 (2) | −0.0096 (19) |
C11 | 0.121 (4) | 0.076 (3) | 0.067 (2) | −0.016 (3) | −0.027 (3) | −0.006 (2) |
C12 | 0.104 (4) | 0.106 (4) | 0.068 (3) | −0.052 (4) | −0.037 (3) | 0.018 (3) |
C13 | 0.063 (3) | 0.108 (4) | 0.071 (3) | −0.019 (3) | −0.018 (2) | 0.025 (3) |
C14 | 0.059 (3) | 0.077 (3) | 0.0555 (19) | −0.009 (2) | −0.001 (2) | 0.014 (2) |
C15 | 0.0551 (19) | 0.0372 (18) | 0.0452 (16) | −0.0031 (19) | 0.0041 (16) | 0.0007 (14) |
C16 | 0.046 (2) | 0.0417 (19) | 0.0542 (18) | −0.0002 (17) | 0.0063 (17) | 0.0043 (16) |
C17 | 0.078 (3) | 0.044 (2) | 0.0492 (18) | 0.002 (2) | 0.006 (2) | 0.0063 (17) |
C18 | 0.086 (6) | 0.060 (5) | 0.071 (4) | 0.021 (5) | −0.019 (5) | −0.027 (3) |
C19 | 0.113 (7) | 0.065 (6) | 0.083 (5) | 0.032 (5) | −0.023 (6) | −0.024 (5) |
C18' | 0.065 (17) | 0.10 (2) | 0.086 (14) | 0.031 (17) | −0.020 (17) | −0.039 (16) |
C19' | 0.13 (4) | 0.13 (3) | 0.13 (2) | −0.02 (3) | 0.00 (3) | −0.01 (2) |
F1 | 0.104 (2) | 0.0759 (17) | 0.0920 (16) | 0.0136 (17) | 0.0071 (16) | −0.0396 (13) |
N1 | 0.065 (2) | 0.0439 (17) | 0.0577 (16) | 0.0022 (17) | −0.0118 (16) | −0.0106 (14) |
N2 | 0.062 (2) | 0.071 (2) | 0.0657 (18) | −0.001 (2) | −0.0089 (17) | 0.0033 (17) |
O1 | 0.0789 (19) | 0.0590 (17) | 0.0833 (17) | 0.0130 (17) | −0.0195 (17) | −0.0171 (15) |
O2 | 0.096 (2) | 0.0507 (16) | 0.0705 (16) | 0.0077 (16) | −0.0151 (17) | −0.0137 (13) |
O3 | 0.098 (2) | 0.0618 (17) | 0.0722 (16) | 0.0301 (18) | −0.0121 (17) | −0.0125 (14) |
C1—F1 | 1.355 (4) | C12—H12 | 0.9300 |
C1—C2 | 1.358 (5) | C13—C14 | 1.367 (6) |
C1—C6 | 1.369 (6) | C13—H13 | 0.9300 |
C2—C3 | 1.387 (4) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.428 (5) |
C3—C4 | 1.386 (5) | C15—C17 | 1.466 (5) |
C3—H3 | 0.9300 | C16—N2 | 1.142 (4) |
C4—C5 | 1.391 (5) | C17—O2 | 1.226 (4) |
C4—C7 | 1.483 (4) | C17—O3 | 1.306 (5) |
C5—C6 | 1.370 (5) | C18—O3 | 1.486 (6) |
C5—H5 | 0.9300 | C18—C19 | 1.511 (8) |
C6—H6 | 0.9300 | C18—H18A | 0.9700 |
C7—C15 | 1.368 (5) | C18—H18B | 0.9700 |
C7—N1 | 1.373 (4) | C19—H19A | 0.9600 |
C8—O1 | 1.207 (4) | C19—H19B | 0.9600 |
C8—N1 | 1.388 (5) | C19—H19C | 0.9600 |
C8—C9 | 1.494 (5) | C18'—O3 | 1.467 (10) |
C9—C10 | 1.384 (5) | C18'—C19' | 1.538 (11) |
C9—C14 | 1.386 (5) | C18'—H18C | 0.9700 |
C10—C11 | 1.384 (6) | C18'—H18D | 0.9700 |
C10—H10 | 0.9300 | C19'—H19D | 0.9600 |
C11—C12 | 1.365 (7) | C19'—H19E | 0.9600 |
C11—H11 | 0.9300 | C19'—H19F | 0.9600 |
C12—C13 | 1.362 (7) | N1—H1 | 0.89 (4) |
F1—C1—C2 | 118.5 (4) | C12—C13—C14 | 121.6 (5) |
F1—C1—C6 | 118.5 (3) | C12—C13—H13 | 119.2 |
C2—C1—C6 | 122.9 (3) | C14—C13—H13 | 119.2 |
C1—C2—C3 | 118.2 (4) | C13—C14—C9 | 119.5 (4) |
C1—C2—H2 | 120.9 | C13—C14—H14 | 120.2 |
C3—C2—H2 | 120.9 | C9—C14—H14 | 120.2 |
C4—C3—C2 | 120.6 (3) | C7—C15—C16 | 118.9 (3) |
C4—C3—H3 | 119.7 | C7—C15—C17 | 123.4 (3) |
C2—C3—H3 | 119.7 | C16—C15—C17 | 117.4 (3) |
C3—C4—C5 | 119.2 (3) | N2—C16—C15 | 176.8 (4) |
C3—C4—C7 | 120.1 (3) | O2—C17—O3 | 122.5 (4) |
C5—C4—C7 | 120.6 (3) | O2—C17—C15 | 124.8 (4) |
C6—C5—C4 | 120.3 (4) | O3—C17—C15 | 112.7 (4) |
C6—C5—H5 | 119.9 | O3—C18—C19 | 105.2 (7) |
C4—C5—H5 | 119.9 | O3—C18—H18A | 110.7 |
C1—C6—C5 | 118.9 (3) | C19—C18—H18A | 110.7 |
C1—C6—H6 | 120.6 | O3—C18—H18B | 110.7 |
C5—C6—H6 | 120.6 | C19—C18—H18B | 110.7 |
C15—C7—N1 | 118.9 (3) | H18A—C18—H18B | 108.8 |
C15—C7—C4 | 120.1 (3) | O3—C18'—C19' | 108 (3) |
N1—C7—C4 | 121.1 (3) | O3—C18'—H18C | 110.2 |
O1—C8—N1 | 123.0 (3) | C19'—C18'—H18C | 110.2 |
O1—C8—C9 | 122.2 (4) | O3—C18'—H18D | 110.2 |
N1—C8—C9 | 114.8 (3) | C19'—C18'—H18D | 110.2 |
C10—C9—C14 | 119.2 (4) | H18C—C18'—H18D | 108.5 |
C10—C9—C8 | 123.8 (4) | C18'—C19'—H19D | 109.5 |
C14—C9—C8 | 117.0 (4) | C18'—C19'—H19E | 109.5 |
C11—C10—C9 | 119.8 (4) | H19D—C19'—H19E | 109.5 |
C11—C10—H10 | 120.1 | C18'—C19'—H19F | 109.5 |
C9—C10—H10 | 120.1 | H19D—C19'—H19F | 109.5 |
C12—C11—C10 | 120.5 (5) | H19E—C19'—H19F | 109.5 |
C12—C11—H11 | 119.8 | C7—N1—C8 | 130.5 (3) |
C10—C11—H11 | 119.8 | C7—N1—H1 | 110 (2) |
C13—C12—C11 | 119.3 (4) | C8—N1—H1 | 119 (2) |
C13—C12—H12 | 120.3 | C17—O3—C18' | 131.2 (16) |
C11—C12—H12 | 120.3 | C17—O3—C18 | 113.5 (4) |
F1—C1—C2—C3 | 179.7 (3) | C10—C9—C14—C13 | 1.4 (5) |
C6—C1—C2—C3 | 0.0 (6) | C8—C9—C14—C13 | 178.7 (3) |
C1—C2—C3—C4 | 0.3 (5) | N1—C7—C15—C16 | −169.8 (3) |
C2—C3—C4—C5 | −0.1 (5) | C4—C7—C15—C16 | 8.7 (4) |
C2—C3—C4—C7 | −176.5 (3) | N1—C7—C15—C17 | 4.2 (5) |
C3—C4—C5—C6 | −0.4 (5) | C4—C7—C15—C17 | −177.2 (3) |
C7—C4—C5—C6 | 176.0 (3) | C7—C15—C16—N2 | 94 (7) |
F1—C1—C6—C5 | 179.7 (4) | C17—C15—C16—N2 | −80 (7) |
C2—C1—C6—C5 | −0.5 (6) | C7—C15—C17—O2 | −4.9 (6) |
C4—C5—C6—C1 | 0.7 (6) | C16—C15—C17—O2 | 169.2 (3) |
C3—C4—C7—C15 | 61.6 (4) | C7—C15—C17—O3 | 176.9 (3) |
C5—C4—C7—C15 | −114.7 (4) | C16—C15—C17—O3 | −8.9 (5) |
C3—C4—C7—N1 | −119.9 (4) | C15—C7—N1—C8 | −173.3 (3) |
C5—C4—C7—N1 | 63.8 (4) | C4—C7—N1—C8 | 8.2 (5) |
O1—C8—C9—C10 | 162.1 (4) | O1—C8—N1—C7 | −5.7 (6) |
N1—C8—C9—C10 | −19.5 (5) | C9—C8—N1—C7 | 175.9 (3) |
O1—C8—C9—C14 | −15.1 (5) | O2—C17—O3—C18' | 25.4 (19) |
N1—C8—C9—C14 | 163.3 (3) | C15—C17—O3—C18' | −156.4 (19) |
C14—C9—C10—C11 | −0.5 (6) | O2—C17—O3—C18 | −0.3 (8) |
C8—C9—C10—C11 | −177.6 (4) | C15—C17—O3—C18 | 177.9 (7) |
C9—C10—C11—C12 | −1.7 (7) | C19'—C18'—O3—C17 | −115 (4) |
C10—C11—C12—C13 | 2.8 (7) | C19'—C18'—O3—C18 | −56 (4) |
C11—C12—C13—C14 | −1.9 (7) | C19—C18—O3—C17 | −175.9 (11) |
C12—C13—C14—C9 | −0.2 (6) | C19—C18—O3—C18' | 48 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.89 (4) | 1.86 (4) | 2.653 (4) | 146 (3) |
C14—H14···O1i | 0.93 | 2.56 | 3.202 (5) | 126 |
C5—H5···N2ii | 0.93 | 2.50 | 3.413 (5) | 167 |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C19H15FN2O3 |
Mr | 338.33 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 292 |
a, b, c (Å) | 6.2149 (5), 14.138 (1), 19.050 (1) |
V (Å3) | 1673.8 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15612, 2109, 1634 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.124, 1.11 |
No. of reflections | 2109 |
No. of parameters | 250 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.17 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0 (10) |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.89 (4) | 1.86 (4) | 2.653 (4) | 146 (3) |
C14—H14···O1i | 0.93 | 2.56 | 3.202 (5) | 126.1 |
C5—H5···N2ii | 0.93 | 2.50 | 3.413 (5) | 167.0 |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x−1, y, z. |
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The title compound is useful as an inhibitor of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al. 2004; Creagh & Hubbell, 1992; Ibers & Hamilton, 1964). Recently, we obtained single crystals of this compound, and its crystal structure is reported here. The molecular conformation is stabilized by intramolecular C—H···O and N—H···O hydrogen bonds (Table 1). The crystal packing is governed by additional C—H···N and C—H···O interactions.