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In the title compound, C19H16N6O4, all ring atoms in the triazolopyrimidinone unit are almost coplanar. The packing of the mol­ecules in the crystal structure is mainly due to inter­molecular C—H...O hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042280/is2085sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042280/is2085Isup2.hkl
Contains datablock I

CCDC reference: 627813

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.048
  • wR factor = 0.142
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N6 - C16 .. 6.13 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6
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 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

6-Isopropyl-5-(3-nitrophenoxy)-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin- 7(6H)-one top
Crystal data top
C19H16N6O4F(000) = 1632
Mr = 392.38Dx = 1.355 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4928 reflections
a = 18.2261 (14) Åθ = 2.2–26.6°
b = 11.6455 (9) ŵ = 0.10 mm1
c = 18.1673 (14) ÅT = 292 K
β = 93.737 (1)°Block, colourless
V = 3847.8 (5) Å30.32 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
4389 independent reflections
Radiation source: fine-focus sealed tube3254 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2323
Tmin = 0.969, Tmax = 0.981k = 1115
13611 measured reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0819P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
4389 reflectionsΔρmax = 0.18 e Å3
265 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0042 (5)
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
C10.14844 (9)0.57996 (15)0.23941 (10)0.0686 (5)
H10.18010.53500.26540.082*
C20.14970 (12)0.69705 (16)0.24577 (12)0.0822 (6)
H20.18220.73130.27650.099*
C30.10373 (11)0.76443 (16)0.20748 (12)0.0800 (6)
H30.10490.84390.21200.096*
C40.05609 (12)0.71322 (16)0.16257 (12)0.0830 (6)
H40.02470.75850.13650.100*
C50.05378 (10)0.59527 (15)0.15526 (10)0.0708 (5)
H50.02140.56120.12440.085*
C60.09999 (8)0.52915 (12)0.19423 (8)0.0514 (4)
C70.07518 (7)0.22573 (12)0.17441 (7)0.0474 (3)
C80.04549 (7)0.33292 (11)0.16928 (7)0.0438 (3)
C90.03457 (8)0.12651 (12)0.15592 (7)0.0495 (3)
C100.05786 (7)0.26797 (12)0.12908 (7)0.0454 (3)
C110.08140 (9)0.05871 (14)0.10423 (9)0.0609 (4)
H110.05140.01050.10840.073*
C120.09446 (12)0.06951 (19)0.02322 (10)0.0886 (6)
H12A0.05060.09740.00300.133*
H12B0.10700.00430.00410.133*
H12C0.13410.12230.01710.133*
C130.14985 (11)0.03869 (17)0.15416 (12)0.0861 (6)
H13A0.18340.10150.14940.129*
H13B0.17290.03150.14040.129*
H13C0.13670.03340.20440.129*
C140.15620 (7)0.38609 (12)0.09341 (8)0.0504 (4)
C150.11842 (8)0.47450 (13)0.05873 (8)0.0523 (4)
H150.06990.46580.04030.063*
C160.15540 (8)0.57705 (14)0.05223 (8)0.0547 (4)
C170.22798 (9)0.59109 (15)0.07633 (9)0.0659 (5)
H170.25160.66110.07110.079*
C180.26462 (9)0.49890 (17)0.10841 (10)0.0708 (5)
H180.31400.50590.12410.085*
C190.22893 (8)0.39623 (15)0.11751 (9)0.0610 (4)
H190.25380.33430.13980.073*
N10.09887 (6)0.40620 (10)0.18803 (6)0.0489 (3)
N20.15978 (7)0.34354 (12)0.20429 (7)0.0603 (4)
N30.14532 (7)0.23524 (12)0.19638 (7)0.0595 (4)
N40.02307 (6)0.35820 (10)0.14883 (6)0.0466 (3)
N50.03553 (6)0.15566 (10)0.13053 (6)0.0481 (3)
N60.11402 (9)0.67514 (13)0.02015 (8)0.0710 (4)
O10.05395 (6)0.02655 (9)0.15910 (7)0.0677 (3)
O20.12488 (5)0.27766 (8)0.10310 (6)0.0590 (3)
O30.04858 (8)0.66428 (12)0.00450 (8)0.0885 (4)
O40.14652 (9)0.76402 (13)0.01074 (12)0.1259 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0682 (10)0.0574 (10)0.0822 (11)0.0069 (8)0.0204 (9)0.0133 (8)
C20.0911 (14)0.0599 (12)0.0979 (14)0.0217 (10)0.0229 (11)0.0075 (10)
C30.0811 (13)0.0495 (10)0.1095 (15)0.0094 (9)0.0065 (11)0.0100 (9)
C40.0786 (12)0.0549 (11)0.1175 (16)0.0041 (9)0.0222 (11)0.0219 (10)
C50.0674 (11)0.0540 (10)0.0936 (12)0.0001 (8)0.0243 (9)0.0089 (9)
C60.0478 (8)0.0475 (9)0.0585 (8)0.0009 (6)0.0015 (6)0.0100 (6)
C70.0433 (7)0.0487 (8)0.0502 (7)0.0133 (6)0.0018 (6)0.0046 (6)
C80.0411 (7)0.0468 (8)0.0431 (7)0.0082 (6)0.0002 (5)0.0044 (6)
C90.0501 (8)0.0452 (8)0.0525 (8)0.0155 (6)0.0009 (6)0.0026 (6)
C100.0413 (7)0.0432 (8)0.0514 (7)0.0097 (6)0.0012 (6)0.0011 (6)
C110.0656 (10)0.0429 (8)0.0750 (10)0.0055 (7)0.0103 (8)0.0095 (7)
C120.1076 (16)0.0826 (14)0.0777 (12)0.0053 (12)0.0224 (11)0.0228 (10)
C130.0840 (13)0.0648 (12)0.1084 (15)0.0207 (10)0.0024 (11)0.0060 (10)
C140.0424 (7)0.0499 (9)0.0601 (8)0.0132 (6)0.0130 (6)0.0049 (6)
C150.0440 (7)0.0590 (10)0.0543 (8)0.0148 (7)0.0056 (6)0.0020 (6)
C160.0539 (9)0.0576 (10)0.0535 (8)0.0156 (7)0.0112 (6)0.0056 (7)
C170.0558 (9)0.0673 (11)0.0757 (10)0.0287 (8)0.0140 (8)0.0023 (8)
C180.0407 (8)0.0824 (13)0.0897 (12)0.0199 (8)0.0088 (8)0.0022 (9)
C190.0402 (8)0.0651 (10)0.0784 (10)0.0049 (7)0.0089 (7)0.0006 (8)
N10.0421 (6)0.0490 (7)0.0559 (7)0.0068 (5)0.0056 (5)0.0055 (5)
N20.0455 (7)0.0603 (9)0.0761 (8)0.0104 (6)0.0111 (6)0.0050 (6)
N30.0478 (7)0.0571 (8)0.0742 (8)0.0130 (6)0.0089 (6)0.0040 (6)
N40.0421 (6)0.0416 (7)0.0562 (7)0.0086 (5)0.0040 (5)0.0017 (5)
N50.0484 (7)0.0404 (7)0.0555 (7)0.0076 (5)0.0033 (5)0.0009 (5)
N60.0756 (10)0.0675 (10)0.0707 (9)0.0202 (8)0.0100 (7)0.0207 (7)
O10.0661 (7)0.0462 (7)0.0915 (8)0.0191 (5)0.0098 (6)0.0002 (5)
O20.0453 (6)0.0459 (6)0.0872 (7)0.0082 (4)0.0147 (5)0.0032 (5)
O30.0780 (9)0.0884 (10)0.0966 (10)0.0109 (7)0.0138 (7)0.0322 (7)
O40.1040 (12)0.0767 (10)0.1974 (19)0.0285 (9)0.0130 (12)0.0531 (11)
Geometric parameters (Å, º) top
C1—C21.369 (2)C11—C131.512 (2)
C1—C61.378 (2)C11—H110.9800
C1—H10.9300C12—H12A0.9600
C2—C31.370 (3)C12—H12B0.9600
C2—H20.9300C12—H12C0.9600
C3—C41.367 (3)C13—H13A0.9600
C3—H30.9300C13—H13B0.9600
C4—C51.381 (2)C13—H13C0.9600
C4—H40.9300C14—C151.369 (2)
C5—C61.372 (2)C14—C191.374 (2)
C5—H50.9300C14—O21.4015 (16)
C6—N11.4365 (19)C15—C161.3801 (19)
C7—C81.3662 (18)C15—H150.9300
C7—N31.3683 (18)C16—C171.376 (2)
C7—C91.424 (2)C16—N61.468 (2)
C8—N11.3544 (17)C17—C181.374 (3)
C8—N41.3589 (16)C17—H170.9300
C9—O11.2189 (16)C18—C191.376 (2)
C9—N51.4272 (17)C18—H180.9300
C10—N41.2902 (17)C19—H190.9300
C10—O21.3426 (16)N1—N21.3764 (16)
C10—N51.3706 (17)N2—N31.2983 (18)
C11—N51.5014 (19)N6—O41.2103 (18)
C11—C121.511 (2)N6—O31.2146 (19)
C2—C1—C6119.55 (15)H12A—C12—H12C109.5
C2—C1—H1120.2H12B—C12—H12C109.5
C6—C1—H1120.2C11—C13—H13A109.5
C1—C2—C3120.89 (17)C11—C13—H13B109.5
C1—C2—H2119.6H13A—C13—H13B109.5
C3—C2—H2119.6C11—C13—H13C109.5
C4—C3—C2119.11 (17)H13A—C13—H13C109.5
C4—C3—H3120.4H13B—C13—H13C109.5
C2—C3—H3120.4C15—C14—C19121.86 (13)
C3—C4—C5121.07 (17)C15—C14—O2122.58 (12)
C3—C4—H4119.5C19—C14—O2115.46 (14)
C5—C4—H4119.5C14—C15—C16117.15 (13)
C6—C5—C4119.02 (16)C14—C15—H15121.4
C6—C5—H5120.5C16—C15—H15121.4
C4—C5—H5120.5C17—C16—C15122.72 (15)
C5—C6—C1120.36 (15)C17—C16—N6119.49 (14)
C5—C6—N1120.45 (13)C15—C16—N6117.77 (13)
C1—C6—N1119.19 (13)C18—C17—C16118.21 (14)
C8—C7—N3109.14 (12)C18—C17—H17120.9
C8—C7—C9120.72 (12)C16—C17—H17120.9
N3—C7—C9130.11 (12)C17—C18—C19120.63 (15)
N1—C8—N4128.37 (12)C17—C18—H18119.7
N1—C8—C7105.32 (11)C19—C18—H18119.7
N4—C8—C7126.31 (13)C14—C19—C18119.35 (16)
O1—C9—C7127.36 (13)C14—C19—H19120.3
O1—C9—N5120.72 (14)C18—C19—H19120.3
C7—C9—N5111.91 (11)C8—N1—N2108.82 (12)
N4—C10—O2120.28 (12)C8—N1—C6131.44 (11)
N4—C10—N5128.31 (12)N2—N1—C6119.72 (11)
O2—C10—N5111.41 (12)N3—N2—N1108.60 (12)
N5—C11—C12111.95 (14)N2—N3—C7108.12 (11)
N5—C11—C13112.32 (13)C10—N4—C8112.14 (11)
C12—C11—C13114.89 (15)C10—N5—C9120.43 (12)
N5—C11—H11105.6C10—N5—C11122.63 (11)
C12—C11—H11105.6C9—N5—C11116.92 (11)
C13—C11—H11105.6O4—N6—O3122.56 (16)
C11—C12—H12A109.5O4—N6—C16118.54 (15)
C11—C12—H12B109.5O3—N6—C16118.89 (13)
H12A—C12—H12B109.5C10—O2—C14120.48 (11)
C11—C12—H12C109.5
C6—C1—C2—C30.4 (3)C5—C6—N1—N2156.79 (15)
C1—C2—C3—C40.1 (3)C1—C6—N1—N222.75 (19)
C2—C3—C4—C50.1 (3)C8—N1—N2—N30.21 (15)
C3—C4—C5—C60.3 (3)C6—N1—N2—N3178.58 (12)
C4—C5—C6—C10.6 (3)N1—N2—N3—C70.41 (16)
C4—C5—C6—N1179.85 (16)C8—C7—N3—N20.47 (16)
C2—C1—C6—C50.6 (3)C9—C7—N3—N2177.51 (14)
C2—C1—C6—N1179.82 (16)O2—C10—N4—C8176.17 (12)
N3—C7—C8—N10.33 (15)N5—C10—N4—C83.8 (2)
C9—C7—C8—N1177.87 (12)N1—C8—N4—C10174.91 (12)
N3—C7—C8—N4179.76 (12)C7—C8—N4—C104.40 (19)
C9—C7—C8—N41.6 (2)N4—C10—N5—C90.4 (2)
C8—C7—C9—O1178.78 (14)O2—C10—N5—C9179.59 (11)
N3—C7—C9—O13.4 (3)N4—C10—N5—C11178.73 (14)
C8—C7—C9—N52.05 (18)O2—C10—N5—C111.25 (18)
N3—C7—C9—N5175.73 (13)O1—C9—N5—C10178.13 (12)
C19—C14—C15—C163.3 (2)C7—C9—N5—C102.64 (18)
O2—C14—C15—C16179.65 (12)O1—C9—N5—C113.44 (19)
C14—C15—C16—C172.6 (2)C7—C9—N5—C11175.79 (12)
C14—C15—C16—N6175.54 (13)C12—C11—N5—C1062.10 (18)
C15—C16—C17—C180.3 (2)C13—C11—N5—C1068.90 (19)
N6—C16—C17—C18177.80 (15)C12—C11—N5—C9116.29 (15)
C16—C17—C18—C191.4 (3)C13—C11—N5—C9112.71 (15)
C15—C14—C19—C181.7 (2)C17—C16—N6—O45.4 (2)
O2—C14—C19—C18178.32 (14)C15—C16—N6—O4176.42 (16)
C17—C18—C19—C140.7 (3)C17—C16—N6—O3174.19 (16)
N4—C8—N1—N2179.50 (13)C15—C16—N6—O34.0 (2)
C7—C8—N1—N20.08 (14)N4—C10—O2—C143.4 (2)
N4—C8—N1—C61.9 (2)N5—C10—O2—C14176.57 (11)
C7—C8—N1—C6178.68 (13)C15—C14—O2—C1047.58 (19)
C5—C6—N1—C824.7 (2)C19—C14—O2—C10135.84 (14)
C1—C6—N1—C8155.73 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.533.319 (2)142
C18—H18···O1ii0.932.463.390 (2)177
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+1/2, z.
 

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