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In the title compound, C16H16N4O3, which displays good herbicidal activity, the planar bicyclic triazolopyrimidine system is bound to an ethyl benzoate moiety via an oxo bridge, with a dihedral angle of 73.98 (2)° between the bicylic triazolopyrimidine system and the benzene ring. In the crystal structure, mol­ecules are linked by inter­molecular C—H...O hydrogen bonds and π–π stacking inter­actions between the triazolopyrimidine rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033763/sj6136sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033763/sj6136Isup2.hkl
Contains datablock I

CCDC reference: 289889

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.051
  • wR factor = 0.128
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 6.15 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Ethyl 2-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-yloxy)benzoate top
Crystal data top
C16H16N4O3F(000) = 656
Mr = 312.33Dx = 1.306 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2092 reflections
a = 9.0013 (13) Åθ = 2.3–21.6°
b = 10.5217 (15) ŵ = 0.09 mm1
c = 17.152 (3) ÅT = 292 K
β = 102.038 (3)°Block, colorless
V = 1588.8 (4) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2093 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 27.0°, θmin = 2.3°
φ and ω scansh = 1110
9593 measured reflectionsk = 613
3470 independent reflectionsl = 2121
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 0.91 w = 1/[σ2(Fo2) + (0.0644P)2]
where P = (Fo2 + 2Fc2)/3
3470 reflections(Δ/σ)max = 0.003
211 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.24 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
C10.3764 (2)0.15737 (17)1.05091 (13)0.0723 (6)
H1A0.33570.21601.00900.108*
H1B0.38070.19741.10160.108*
H1C0.47680.13241.04630.108*
C20.2764 (2)0.04238 (16)1.04429 (11)0.0529 (5)
C30.1942 (2)0.01446 (17)1.10334 (10)0.0554 (5)
H30.20670.06591.14830.066*
C40.0970 (2)0.08568 (16)1.09658 (9)0.0495 (4)
C50.0020 (2)0.12361 (19)1.15375 (10)0.0652 (5)
H5A0.04050.20121.17970.098*
H5B0.00480.05791.19290.098*
H5C0.10090.13621.12560.098*
C60.17278 (19)0.12849 (15)0.97284 (9)0.0455 (4)
C70.03910 (19)0.28673 (15)0.93792 (9)0.0457 (4)
C80.0403 (2)0.43507 (16)0.83608 (10)0.0489 (4)
C90.1316 (2)0.53948 (18)0.85550 (11)0.0633 (5)
H90.14770.57340.90670.076*
C100.1994 (2)0.59379 (18)0.79864 (13)0.0682 (6)
H100.26140.66460.81160.082*
C110.1761 (2)0.54420 (18)0.72316 (12)0.0638 (5)
H110.22230.58120.68500.077*
C120.0839 (2)0.43939 (17)0.70397 (10)0.0560 (5)
H120.06910.40560.65280.067*
C130.01232 (19)0.38311 (15)0.75992 (10)0.0481 (4)
C140.0934 (2)0.27458 (17)0.73765 (11)0.0572 (5)
C150.1682 (3)0.1073 (2)0.64504 (13)0.0827 (7)
H15A0.27250.13640.62980.099*
H15B0.16230.04390.68670.099*
C160.1190 (4)0.0519 (3)0.57549 (17)0.1243 (10)
H16A0.11340.11770.53740.186*
H16B0.19080.01140.55140.186*
H16C0.02080.01360.59250.186*
N10.26752 (16)0.02903 (13)0.97933 (8)0.0519 (4)
N20.08897 (16)0.15618 (12)1.02918 (7)0.0444 (3)
N30.00021 (16)0.26124 (13)1.00644 (8)0.0473 (4)
N40.14090 (16)0.21337 (13)0.91347 (8)0.0492 (4)
O10.02912 (14)0.38772 (11)0.89632 (7)0.0581 (4)
O20.19345 (18)0.24522 (13)0.77099 (8)0.0815 (5)
O30.06801 (16)0.21351 (12)0.67368 (8)0.0734 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0623 (13)0.0614 (13)0.0899 (15)0.0051 (10)0.0082 (11)0.0141 (11)
C20.0466 (10)0.0465 (11)0.0619 (11)0.0081 (8)0.0031 (9)0.0021 (9)
C30.0609 (12)0.0545 (12)0.0487 (10)0.0128 (9)0.0066 (9)0.0093 (9)
C40.0558 (11)0.0501 (11)0.0423 (9)0.0136 (9)0.0098 (8)0.0021 (8)
C50.0787 (14)0.0738 (14)0.0481 (11)0.0082 (11)0.0245 (10)0.0047 (9)
C60.0454 (10)0.0495 (10)0.0427 (9)0.0039 (8)0.0120 (8)0.0021 (8)
C70.0501 (10)0.0475 (10)0.0411 (9)0.0009 (8)0.0134 (8)0.0002 (8)
C80.0526 (11)0.0511 (11)0.0467 (10)0.0124 (8)0.0185 (8)0.0093 (8)
C90.0701 (13)0.0624 (13)0.0588 (12)0.0013 (10)0.0168 (10)0.0041 (10)
C100.0695 (14)0.0617 (13)0.0766 (14)0.0056 (10)0.0224 (11)0.0014 (11)
C110.0637 (13)0.0662 (13)0.0678 (13)0.0037 (10)0.0280 (10)0.0161 (10)
C120.0616 (12)0.0616 (12)0.0470 (10)0.0090 (9)0.0165 (9)0.0088 (9)
C130.0492 (10)0.0474 (10)0.0484 (10)0.0086 (8)0.0120 (8)0.0076 (8)
C140.0607 (13)0.0570 (12)0.0517 (11)0.0084 (10)0.0068 (9)0.0124 (9)
C150.0890 (17)0.0633 (14)0.0860 (16)0.0039 (12)0.0044 (13)0.0054 (12)
C160.125 (2)0.121 (2)0.124 (2)0.0128 (19)0.0178 (19)0.0581 (19)
N10.0509 (9)0.0508 (9)0.0549 (9)0.0002 (7)0.0130 (7)0.0032 (7)
N20.0504 (8)0.0448 (8)0.0389 (7)0.0064 (6)0.0116 (6)0.0001 (6)
N30.0551 (9)0.0482 (9)0.0410 (7)0.0002 (7)0.0156 (6)0.0001 (6)
N40.0563 (9)0.0521 (9)0.0428 (8)0.0049 (7)0.0183 (7)0.0044 (6)
O10.0666 (8)0.0623 (8)0.0516 (7)0.0172 (6)0.0264 (6)0.0147 (6)
O20.0862 (11)0.0899 (11)0.0721 (9)0.0229 (8)0.0251 (9)0.0091 (8)
O30.0740 (10)0.0682 (9)0.0777 (9)0.0038 (7)0.0153 (8)0.0166 (7)
Geometric parameters (Å, º) top
C1—C21.498 (2)C8—O11.4056 (18)
C1—H1A0.9600C9—C101.378 (2)
C1—H1B0.9600C9—H90.9300
C1—H1C0.9600C10—C111.371 (3)
C2—N11.332 (2)C10—H100.9300
C2—C31.404 (2)C11—C121.378 (2)
C3—C41.359 (2)C11—H110.9300
C3—H30.9300C12—C131.394 (2)
C4—N21.3627 (19)C12—H120.9300
C4—C51.484 (2)C13—C141.485 (2)
C5—H5A0.9600C14—O21.203 (2)
C5—H5B0.9600C14—O31.332 (2)
C5—H5C0.9600C15—O31.456 (2)
C6—N11.340 (2)C15—C161.476 (3)
C6—N41.3399 (19)C15—H15A0.9700
C6—N21.3755 (19)C15—H15B0.9700
C7—N31.324 (2)C16—H16A0.9600
C7—N41.331 (2)C16—H16B0.9600
C7—O11.3537 (19)C16—H16C0.9600
C8—C91.371 (2)N2—N31.3740 (18)
C8—C131.390 (2)
C2—C1—H1A109.5C11—C10—H10119.8
C2—C1—H1B109.5C9—C10—H10119.8
H1A—C1—H1B109.5C10—C11—C12119.74 (18)
C2—C1—H1C109.5C10—C11—H11120.1
H1A—C1—H1C109.5C12—C11—H11120.1
H1B—C1—H1C109.5C11—C12—C13121.14 (17)
N1—C2—C3122.45 (16)C11—C12—H12119.4
N1—C2—C1116.68 (17)C13—C12—H12119.4
C3—C2—C1120.86 (17)C8—C13—C12117.43 (17)
C4—C3—C2121.83 (16)C8—C13—C14121.68 (15)
C4—C3—H3119.1C12—C13—C14120.86 (16)
C2—C3—H3119.1O2—C14—O3122.81 (19)
C3—C4—N2114.43 (16)O2—C14—C13125.33 (18)
C3—C4—C5126.99 (16)O3—C14—C13111.83 (17)
N2—C4—C5118.58 (16)O3—C15—C16107.8 (2)
C4—C5—H5A109.5O3—C15—H15A110.1
C4—C5—H5B109.5C16—C15—H15A110.1
H5A—C5—H5B109.5O3—C15—H15B110.1
C4—C5—H5C109.5C16—C15—H15B110.1
H5A—C5—H5C109.5H15A—C15—H15B108.5
H5B—C5—H5C109.5C15—C16—H16A109.5
N1—C6—N4127.98 (15)C15—C16—H16B109.5
N1—C6—N2122.68 (15)H16A—C16—H16B109.5
N4—C6—N2109.33 (14)C15—C16—H16C109.5
N3—C7—N4119.43 (15)H16A—C16—H16C109.5
N3—C7—O1116.81 (14)H16B—C16—H16C109.5
N4—C7—O1123.75 (14)C2—N1—C6115.85 (15)
C9—C8—C13121.71 (16)C4—N2—N3127.10 (14)
C9—C8—O1116.19 (15)C4—N2—C6122.74 (15)
C13—C8—O1122.03 (16)N3—N2—C6110.16 (12)
C8—C9—C10119.47 (18)C7—N3—N299.58 (13)
C8—C9—H9120.3C7—N4—C6101.50 (13)
C10—C9—H9120.3C7—O1—C8116.31 (12)
C11—C10—C9120.50 (19)C14—O3—C15116.58 (17)
N1—C2—C3—C41.9 (3)C3—C4—N2—N3179.29 (15)
C1—C2—C3—C4176.62 (16)C5—C4—N2—N30.6 (2)
C2—C3—C4—N21.1 (2)C3—C4—N2—C60.2 (2)
C2—C3—C4—C5178.79 (16)C5—C4—N2—C6179.92 (15)
C13—C8—C9—C100.9 (3)N1—C6—N2—C40.9 (2)
O1—C8—C9—C10177.81 (16)N4—C6—N2—C4179.73 (14)
C8—C9—C10—C110.0 (3)N1—C6—N2—N3178.74 (14)
C9—C10—C11—C120.1 (3)N4—C6—N2—N30.14 (18)
C10—C11—C12—C130.6 (3)N4—C7—N3—N20.15 (19)
C9—C8—C13—C121.5 (3)O1—C7—N3—N2179.56 (13)
O1—C8—C13—C12178.30 (14)C4—N2—N3—C7179.57 (15)
C9—C8—C13—C14176.48 (16)C6—N2—N3—C70.00 (16)
O1—C8—C13—C140.3 (2)N3—C7—N4—C60.2 (2)
C11—C12—C13—C81.4 (3)O1—C7—N4—C6179.46 (15)
C11—C12—C13—C14176.65 (15)N1—C6—N4—C7178.59 (16)
C8—C13—C14—O222.2 (3)N2—C6—N4—C70.21 (17)
C12—C13—C14—O2155.71 (18)N3—C7—O1—C8163.43 (15)
C8—C13—C14—O3159.56 (15)N4—C7—O1—C816.9 (2)
C12—C13—C14—O322.5 (2)C9—C8—O1—C798.75 (18)
C3—C2—N1—C61.2 (2)C13—C8—O1—C784.32 (19)
C1—C2—N1—C6177.35 (15)O2—C14—O3—C150.1 (3)
N4—C6—N1—C2178.77 (16)C13—C14—O3—C15178.31 (14)
N2—C6—N1—C20.1 (2)C16—C15—O3—C14178.88 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.932.363.248 (2)160
Symmetry code: (i) x, y, z+2.
 

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