Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052956/sj2388sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052956/sj2388Isup2.hkl |
CCDC reference: 667485
The title compound was obtained from Rallis India, Bangalore. Single crystals of the compound were grown by the slow evaporation method from acetone at 278 K.
Despite repeated attempts to grow a better quality crystal with improved morphology, the crystals obtained were small and weakly diffracting so that the extent of diffraction observed is poor. The carbonyl oxygen atom is disordered over two sites O4 and O4A, with the occupancy factor for the major disorder component, O4, refining to 0.517 (11). All the hydrogen atoms were placed in calculated positions and allowed to ride on the parent atoms with C—H = 0.93 - 0.96 Å and Ueq(H) = 1.2 or 1.5 Ueq(C).
An important aspect in the rational design of bioactive molecules involves relating chemical structure to biological activity (Lewis et al., 1991). The conformation of the molecule is found to influence the levels of biological activity. Correlation of the results obtained from X-ray crystallography with biological activity has aided in the chemical design of few active agrochemicals. The activity of a series of triazolyl ketone herbicides (Anderson et al., 1983) has been investigated along with the fungicidal activities of N-phenyl succinamides (Zenei et al., 1988).
The title compound, (I), has been shown to have fungicidal properties and its structure is reported here, Fig. 1. Bond lengths and angles observed in the structure are normal (Allen et al., 1987). The crystal structure is stabilized by aromatic stacking π···π interactions (Fig. 2) between the pyrimidyl rings, the centroid to centroid distance being 3.914 (9) Å (Symmetry Code: -x + 1/2, -y + 3 /2, -z + 1).
For related structures, see: Lewis et al. (1991); Anderson et al. (1983); Zenei et al. (1988).
For related literature, see: Allen et al. (1987).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).
Fig. 1. Molecular structure of (I), showing 50% ellipsoidal probability. | |
Fig. 2. Part of the packing diagram for (I), highlighting the π···π intermolecular interactions (dotted line). |
C22H16N3O5 | F(000) = 1672 |
Mr = 402.38 | Dx = 1.289 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 565 reflections |
a = 28.946 (6) Å | θ = 1.2–19.6° |
b = 10.803 (2) Å | µ = 0.09 mm−1 |
c = 13.302 (3) Å | T = 292 K |
β = 94.61 (3)° | Plate, colorless |
V = 4146.1 (15) Å3 | 0.08 × 0.07 × 0.02 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 2169 independent reflections |
Radiation source: fine-focus sealed tube | 1733 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
φ and ω scans | θmax = 20.8°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997a) | h = −28→28 |
Tmin = 0.948, Tmax = 0.998 | k = −10→10 |
9000 measured reflections | l = −13→13 |
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)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.220 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.1574P)2 + 9.0867P] where P = (Fo2 + 2Fc2)/3 |
2169 reflections | (Δ/σ)max < 0.001 |
283 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C22H16N3O5 | V = 4146.1 (15) Å3 |
Mr = 402.38 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 28.946 (6) Å | µ = 0.09 mm−1 |
b = 10.803 (2) Å | T = 292 K |
c = 13.302 (3) Å | 0.08 × 0.07 × 0.02 mm |
β = 94.61 (3)° |
Bruker SMART CCD area-detector diffractometer | 2169 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997a) | 1733 reflections with I > 2σ(I) |
Tmin = 0.948, Tmax = 0.998 | Rint = 0.055 |
9000 measured reflections | θmax = 20.8° |
R[F2 > 2σ(F2)] = 0.079 | 0 restraints |
wR(F2) = 0.220 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.31 e Å−3 |
2169 reflections | Δρmin = −0.39 e Å−3 |
283 parameters |
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) | |
O1 | 0.72469 (11) | 0.4309 (3) | 0.3502 (2) | 0.0658 (10) | |
O2 | 0.62147 (10) | 0.1461 (3) | 0.4936 (2) | 0.0648 (9) | |
O3 | 0.51541 (13) | 0.2021 (4) | 0.4877 (3) | 0.0971 (13) | |
O4 | 0.5153 (3) | 0.4039 (9) | 0.4684 (6) | 0.103 (4) | 0.517 (11) |
O4A | 0.5367 (3) | 0.4936 (7) | 0.2981 (7) | 0.106 (4) | 0.483 (11) |
O5 | 0.58850 (14) | 0.3775 (3) | 0.2208 (3) | 0.0872 (12) | |
N1 | 0.63577 (19) | 0.6404 (5) | 0.4033 (4) | 0.1047 (17) | |
N2 | 0.72237 (14) | 0.4148 (3) | 0.5245 (3) | 0.0660 (12) | |
N3 | 0.67012 (15) | 0.2677 (4) | 0.5918 (3) | 0.0707 (12) | |
C1 | 0.7935 (2) | 0.7708 (5) | 0.3623 (4) | 0.0715 (15) | |
C2 | 0.81804 (17) | 0.6609 (5) | 0.3512 (4) | 0.0713 (14) | |
C3 | 0.79544 (16) | 0.5464 (4) | 0.3512 (3) | 0.0631 (13) | |
C4 | 0.74871 (16) | 0.5440 (4) | 0.3622 (3) | 0.0530 (12) | |
C5 | 0.72374 (15) | 0.6540 (4) | 0.3753 (3) | 0.0575 (13) | |
C6 | 0.74707 (18) | 0.7679 (5) | 0.3748 (3) | 0.0650 (13) | |
C7 | 0.6746 (2) | 0.6477 (5) | 0.3900 (4) | 0.0736 (15) | |
C8 | 0.70679 (15) | 0.3777 (4) | 0.4317 (3) | 0.0519 (12) | |
C9 | 0.7029 (2) | 0.3558 (5) | 0.5980 (4) | 0.0783 (16) | |
C10 | 0.65564 (15) | 0.2350 (4) | 0.4959 (3) | 0.0517 (12) | |
C11 | 0.67341 (14) | 0.2847 (4) | 0.4135 (3) | 0.0527 (12) | |
C12 | 0.60626 (15) | 0.0952 (4) | 0.3966 (3) | 0.0565 (12) | |
C13 | 0.62339 (17) | −0.0210 (5) | 0.3743 (4) | 0.0727 (14) | |
C14 | 0.60929 (19) | −0.0757 (5) | 0.2829 (4) | 0.0801 (16) | |
C15 | 0.57760 (18) | −0.0146 (5) | 0.2143 (4) | 0.0806 (16) | |
C16 | 0.56032 (16) | 0.1001 (5) | 0.2397 (4) | 0.0687 (14) | |
C17 | 0.57395 (14) | 0.1586 (4) | 0.3327 (3) | 0.0561 (12) | |
C18 | 0.55490 (15) | 0.2839 (4) | 0.3569 (4) | 0.0621 (14) | |
C19 | 0.52730 (19) | 0.3029 (6) | 0.4364 (5) | 0.0782 (16) | |
C20 | 0.4827 (3) | 0.2207 (9) | 0.5632 (7) | 0.155 (3) | |
C21 | 0.5617 (2) | 0.3891 (6) | 0.2961 (5) | 0.0779 (16) | |
C22 | 0.5905 (2) | 0.4881 (7) | 0.1568 (6) | 0.123 (3) | |
H1 | 0.8088 | 0.8464 | 0.3611 | 0.086* | |
H2 | 0.8497 | 0.6639 | 0.3438 | 0.086* | |
H3 | 0.8118 | 0.4733 | 0.3439 | 0.076* | |
H6 | 0.7310 | 0.8413 | 0.3829 | 0.078* | |
H9 | 0.7136 | 0.3790 | 0.6631 | 0.094* | |
H11 | 0.6639 | 0.2584 | 0.3485 | 0.063* | |
H13 | 0.6441 | −0.0614 | 0.4203 | 0.087* | |
H14 | 0.6208 | −0.1530 | 0.2669 | 0.096* | |
H15 | 0.5683 | −0.0506 | 0.1525 | 0.097* | |
H16 | 0.5392 | 0.1398 | 0.1943 | 0.082* | |
H20A | 0.4989 | 0.2502 | 0.6244 | 0.233* | |
H20B | 0.4677 | 0.1438 | 0.5760 | 0.233* | |
H20C | 0.4599 | 0.2806 | 0.5392 | 0.233* | |
H22A | 0.5659 | 0.5436 | 0.1705 | 0.185* | |
H22B | 0.5872 | 0.4640 | 0.0871 | 0.185* | |
H22C | 0.6198 | 0.5288 | 0.1711 | 0.185* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.076 (2) | 0.063 (2) | 0.056 (2) | −0.0193 (17) | −0.0109 (16) | −0.0068 (16) |
O2 | 0.063 (2) | 0.065 (2) | 0.063 (2) | −0.0096 (17) | −0.0157 (16) | 0.0085 (16) |
O3 | 0.069 (2) | 0.116 (3) | 0.107 (3) | 0.010 (2) | 0.009 (2) | 0.009 (3) |
O4 | 0.092 (6) | 0.115 (7) | 0.102 (6) | 0.036 (5) | 0.000 (4) | −0.027 (5) |
O4A | 0.120 (7) | 0.058 (6) | 0.134 (8) | 0.004 (5) | −0.021 (5) | −0.006 (5) |
O5 | 0.089 (3) | 0.068 (3) | 0.100 (3) | 0.003 (2) | −0.016 (2) | 0.023 (2) |
N1 | 0.068 (3) | 0.112 (4) | 0.132 (5) | 0.013 (3) | −0.004 (3) | 0.011 (3) |
N2 | 0.087 (3) | 0.053 (2) | 0.053 (3) | −0.008 (2) | −0.028 (2) | 0.000 (2) |
N3 | 0.097 (3) | 0.058 (3) | 0.053 (3) | −0.007 (2) | −0.017 (2) | 0.007 (2) |
C1 | 0.085 (4) | 0.061 (3) | 0.067 (3) | −0.018 (3) | −0.010 (3) | 0.005 (2) |
C2 | 0.054 (3) | 0.078 (4) | 0.079 (3) | −0.010 (3) | −0.013 (2) | 0.009 (3) |
C3 | 0.056 (3) | 0.061 (3) | 0.070 (3) | 0.001 (3) | −0.011 (2) | 0.008 (2) |
C4 | 0.057 (3) | 0.052 (3) | 0.046 (3) | −0.010 (2) | −0.019 (2) | 0.001 (2) |
C5 | 0.054 (3) | 0.064 (3) | 0.051 (3) | −0.002 (3) | −0.017 (2) | 0.002 (2) |
C6 | 0.072 (4) | 0.059 (3) | 0.062 (3) | 0.004 (3) | −0.011 (2) | 0.002 (2) |
C7 | 0.072 (4) | 0.071 (4) | 0.075 (3) | 0.009 (3) | −0.014 (3) | 0.003 (3) |
C8 | 0.056 (3) | 0.046 (3) | 0.050 (3) | 0.008 (2) | −0.015 (2) | 0.000 (2) |
C9 | 0.118 (4) | 0.061 (3) | 0.050 (3) | −0.018 (3) | −0.027 (3) | 0.006 (3) |
C10 | 0.055 (3) | 0.041 (3) | 0.056 (3) | 0.005 (2) | −0.018 (2) | 0.005 (2) |
C11 | 0.051 (3) | 0.051 (3) | 0.053 (3) | −0.005 (2) | −0.019 (2) | −0.005 (2) |
C12 | 0.052 (3) | 0.051 (3) | 0.064 (3) | −0.004 (2) | −0.009 (2) | 0.001 (2) |
C13 | 0.069 (3) | 0.065 (4) | 0.082 (4) | 0.002 (3) | −0.012 (3) | 0.002 (3) |
C14 | 0.079 (4) | 0.058 (3) | 0.101 (4) | 0.004 (3) | −0.008 (3) | −0.004 (3) |
C15 | 0.074 (4) | 0.073 (4) | 0.093 (4) | −0.020 (3) | −0.003 (3) | −0.019 (3) |
C16 | 0.045 (3) | 0.072 (4) | 0.086 (4) | −0.004 (2) | −0.018 (2) | −0.007 (3) |
C17 | 0.043 (3) | 0.056 (3) | 0.066 (3) | −0.006 (2) | −0.014 (2) | −0.001 (2) |
C18 | 0.046 (3) | 0.068 (4) | 0.068 (3) | 0.000 (2) | −0.020 (3) | −0.009 (3) |
C19 | 0.057 (3) | 0.085 (4) | 0.089 (4) | 0.005 (3) | −0.020 (3) | −0.008 (4) |
C20 | 0.114 (6) | 0.220 (10) | 0.137 (7) | 0.023 (6) | 0.040 (6) | 0.028 (6) |
C21 | 0.067 (4) | 0.079 (4) | 0.084 (4) | −0.010 (3) | −0.024 (3) | −0.002 (3) |
C22 | 0.116 (5) | 0.111 (5) | 0.137 (6) | −0.019 (4) | −0.030 (4) | 0.033 (5) |
O4—C19 | 1.230 (9) | C18—C21 | 1.418 (8) |
O4A—C21 | 1.342 (10) | C4—C3 | 1.372 (7) |
O1—C8 | 1.366 (5) | C2—C1 | 1.398 (7) |
O1—C4 | 1.409 (6) | C2—C3 | 1.399 (7) |
O2—C10 | 1.377 (5) | C2—H2 | 0.9300 |
O2—C12 | 1.439 (6) | N1—C7 | 1.154 (7) |
N2—C9 | 1.329 (6) | C3—H3 | 0.9300 |
N2—C8 | 1.342 (6) | C13—C14 | 1.384 (7) |
O5—C21 | 1.321 (7) | C13—H13 | 0.9300 |
O5—C22 | 1.471 (8) | C6—C1 | 1.367 (7) |
O3—C19 | 1.345 (7) | C6—H6 | 0.9300 |
O3—C20 | 1.448 (8) | C14—C15 | 1.406 (8) |
C10—N3 | 1.357 (6) | C14—H14 | 0.9300 |
C10—C11 | 1.358 (6) | C15—C16 | 1.388 (7) |
N3—C9 | 1.342 (7) | C15—H15 | 0.9300 |
C17—C12 | 1.392 (6) | C9—H9 | 0.9300 |
C17—C16 | 1.417 (7) | C16—H16 | 0.9300 |
C17—C18 | 1.506 (7) | C1—H1 | 0.9300 |
C8—C11 | 1.401 (6) | C22—H22A | 0.9600 |
C11—H11 | 0.9300 | C22—H22B | 0.9600 |
C12—C13 | 1.390 (7) | C22—H22C | 0.9600 |
C5—C6 | 1.404 (7) | C20—H20A | 0.9600 |
C5—C4 | 1.409 (7) | C20—H20B | 0.9600 |
C5—C7 | 1.453 (8) | C20—H20C | 0.9600 |
C18—C19 | 1.391 (8) | ||
C8—O1—C4 | 119.4 (3) | C12—C13—H13 | 120.4 |
C10—O2—C12 | 116.9 (3) | N1—C7—C5 | 178.3 (6) |
C9—N2—C8 | 113.8 (4) | C1—C6—C5 | 119.9 (5) |
C21—O5—C22 | 114.5 (5) | C1—C6—H6 | 120.0 |
C19—O3—C20 | 116.6 (6) | C5—C6—H6 | 120.0 |
N3—C10—C11 | 123.2 (4) | O5—C21—O4A | 116.5 (6) |
N3—C10—O2 | 111.7 (4) | O5—C21—C18 | 118.2 (5) |
C11—C10—O2 | 125.2 (4) | O4A—C21—C18 | 124.3 (7) |
C9—N3—C10 | 114.0 (4) | C13—C14—C15 | 120.0 (5) |
C12—C17—C16 | 116.1 (4) | C13—C14—H14 | 120.0 |
C12—C17—C18 | 123.4 (4) | C15—C14—H14 | 120.0 |
C16—C17—C18 | 120.4 (4) | O4—C19—O3 | 116.9 (7) |
N2—C8—O1 | 119.0 (4) | O4—C19—C18 | 126.0 (7) |
N2—C8—C11 | 123.3 (4) | O3—C19—C18 | 116.8 (6) |
O1—C8—C11 | 117.7 (4) | C16—C15—C14 | 119.4 (5) |
C10—C11—C8 | 116.4 (4) | C16—C15—H15 | 120.3 |
C10—C11—H11 | 121.8 | C14—C15—H15 | 120.3 |
C8—C11—H11 | 121.8 | N2—C9—N3 | 129.4 (4) |
C13—C12—C17 | 123.2 (4) | N2—C9—H9 | 115.3 |
C13—C12—O2 | 116.6 (4) | N3—C9—H9 | 115.3 |
C17—C12—O2 | 120.1 (4) | C15—C16—C17 | 122.0 (5) |
C6—C5—C4 | 119.1 (4) | C15—C16—H16 | 119.0 |
C6—C5—C7 | 121.2 (4) | C17—C16—H16 | 119.0 |
C4—C5—C7 | 119.6 (4) | C6—C1—C2 | 120.4 (5) |
C19—C18—C21 | 115.4 (5) | C6—C1—H1 | 119.8 |
C19—C18—C17 | 122.5 (5) | C2—C1—H1 | 119.8 |
C21—C18—C17 | 121.9 (5) | O5—C22—H22A | 109.5 |
C3—C4—O1 | 119.1 (4) | O5—C22—H22B | 109.5 |
C3—C4—C5 | 121.1 (4) | H22A—C22—H22B | 109.5 |
O1—C4—C5 | 119.5 (4) | O5—C22—H22C | 109.5 |
C1—C2—C3 | 120.6 (5) | H22A—C22—H22C | 109.5 |
C1—C2—H2 | 119.7 | H22B—C22—H22C | 109.5 |
C3—C2—H2 | 119.7 | O3—C20—H20A | 109.5 |
C4—C3—C2 | 118.8 (4) | O3—C20—H20B | 109.5 |
C4—C3—H3 | 120.6 | H20A—C20—H20B | 109.5 |
C2—C3—H3 | 120.6 | O3—C20—H20C | 109.5 |
C14—C13—C12 | 119.2 (5) | H20A—C20—H20C | 109.5 |
C14—C13—H13 | 120.4 | H20B—C20—H20C | 109.5 |
C12—O2—C10—N3 | −174.3 (3) | O1—C4—C3—C2 | 172.4 (4) |
C12—O2—C10—C11 | 5.3 (6) | C5—C4—C3—C2 | −1.2 (6) |
C11—C10—N3—C9 | 1.4 (7) | C1—C2—C3—C4 | 0.0 (7) |
O2—C10—N3—C9 | −178.9 (4) | C17—C12—C13—C14 | 2.4 (7) |
C9—N2—C8—O1 | −179.3 (4) | O2—C12—C13—C14 | 178.8 (4) |
C9—N2—C8—C11 | −0.5 (6) | C4—C5—C6—C1 | −0.4 (6) |
C4—O1—C8—N2 | −17.4 (6) | C7—C5—C6—C1 | 179.0 (4) |
C4—O1—C8—C11 | 163.7 (4) | C22—O5—C21—O4A | 6.3 (7) |
N3—C10—C11—C8 | −2.8 (6) | C22—O5—C21—C18 | 175.2 (5) |
O2—C10—C11—C8 | 177.6 (4) | C19—C18—C21—O5 | 178.4 (4) |
N2—C8—C11—C10 | 2.4 (6) | C17—C18—C21—O5 | −5.2 (7) |
O1—C8—C11—C10 | −178.8 (4) | C19—C18—C21—O4A | −13.7 (8) |
C16—C17—C12—C13 | −2.5 (7) | C17—C18—C21—O4A | 162.7 (6) |
C18—C17—C12—C13 | 179.4 (4) | C12—C13—C14—C15 | −0.7 (8) |
C16—C17—C12—O2 | −178.7 (4) | C20—O3—C19—O4 | 11.1 (9) |
C18—C17—C12—O2 | 3.2 (6) | C20—O3—C19—C18 | −173.6 (5) |
C10—O2—C12—C13 | 101.8 (5) | C21—C18—C19—O4 | −13.3 (8) |
C10—O2—C12—C17 | −81.7 (5) | C17—C18—C19—O4 | 170.4 (6) |
C12—C17—C18—C19 | −65.7 (6) | C21—C18—C19—O3 | 171.9 (4) |
C16—C17—C18—C19 | 116.2 (5) | C17—C18—C19—O3 | −4.5 (7) |
C12—C17—C18—C21 | 118.1 (5) | C13—C14—C15—C16 | −0.7 (8) |
C16—C17—C18—C21 | −59.9 (6) | C8—N2—C9—N3 | −1.1 (8) |
C8—O1—C4—C3 | 112.7 (4) | C10—N3—C9—N2 | 0.7 (8) |
C8—O1—C4—C5 | −73.5 (5) | C14—C15—C16—C17 | 0.6 (8) |
C6—C5—C4—C3 | 1.4 (6) | C12—C17—C16—C15 | 1.0 (7) |
C7—C5—C4—C3 | −178.0 (4) | C18—C17—C16—C15 | 179.2 (4) |
C6—C5—C4—O1 | −172.2 (4) | C5—C6—C1—C2 | −0.8 (7) |
C7—C5—C4—O1 | 8.4 (6) | C3—C2—C1—C6 | 1.0 (7) |
Experimental details
Crystal data | |
Chemical formula | C22H16N3O5 |
Mr | 402.38 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 292 |
a, b, c (Å) | 28.946 (6), 10.803 (2), 13.302 (3) |
β (°) | 94.61 (3) |
V (Å3) | 4146.1 (15) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.08 × 0.07 × 0.02 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997a) |
Tmin, Tmax | 0.948, 0.998 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9000, 2169, 1733 |
Rint | 0.055 |
θmax (°) | 20.8 |
(sin θ/λ)max (Å−1) | 0.500 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.079, 0.220, 1.14 |
No. of reflections | 2169 |
No. of parameters | 283 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.39 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997b), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).
An important aspect in the rational design of bioactive molecules involves relating chemical structure to biological activity (Lewis et al., 1991). The conformation of the molecule is found to influence the levels of biological activity. Correlation of the results obtained from X-ray crystallography with biological activity has aided in the chemical design of few active agrochemicals. The activity of a series of triazolyl ketone herbicides (Anderson et al., 1983) has been investigated along with the fungicidal activities of N-phenyl succinamides (Zenei et al., 1988).
The title compound, (I), has been shown to have fungicidal properties and its structure is reported here, Fig. 1. Bond lengths and angles observed in the structure are normal (Allen et al., 1987). The crystal structure is stabilized by aromatic stacking π···π interactions (Fig. 2) between the pyrimidyl rings, the centroid to centroid distance being 3.914 (9) Å (Symmetry Code: -x + 1/2, -y + 3 /2, -z + 1).