Download citation
Download citation
link to html
The title compound, C15H12F3N5O3, is a by-product isolated from the preparation of di-2-pyridiylglycoluril. The mol­ecule contains two classical intra­molecular N—H...N and N—H...O hydrogen bonds, and its crystal structure is stabilized mostly by inter­molecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054109/bh2069sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054109/bh2069IIsup2.hkl
Contains datablock II

CCDC reference: 633605

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.058
  • wR factor = 0.177
  • Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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, 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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

1-Picolinoyl-3-[(2-pyridyl)(2,2,2-trifluoroacetamido)methyl]urea top
Crystal data top
C15H12F3N5O3Z = 2
Mr = 367.30F(000) = 376
Triclinic, P1Dx = 1.520 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.9095 (12) ÅCell parameters from 959 reflections
b = 12.754 (3) Åθ = 2.3–21.9°
c = 13.072 (3) ŵ = 0.13 mm1
α = 85.969 (4)°T = 292 K
β = 79.721 (4)°Block, colourless
γ = 86.585 (4)°0.30 × 0.20 × 0.10 mm
V = 802.4 (3) Å3
Data collection top
Bruker SMART 4 K CCD area-detector
diffractometer
1725 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 1.6°
φ and ω scansh = 55
3937 measured reflectionsk = 1215
2775 independent reflectionsl = 1515
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0912P)2]
where P = (Fo2 + 2Fc2)/3
2775 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.23 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1702 (8)0.6351 (3)0.9945 (3)0.0710 (11)
H10.00750.61431.03720.085*
C20.2648 (9)0.7311 (3)1.0071 (3)0.0754 (11)
H20.17050.77351.05830.090*
C30.4966 (9)0.7635 (3)0.9444 (3)0.0845 (13)
H30.56170.82940.95030.101*
C40.6375 (8)0.6968 (3)0.8704 (3)0.0673 (11)
H40.80090.71630.82730.081*
C50.5284 (6)0.6020 (2)0.8630 (2)0.0451 (8)
C60.6723 (6)0.5253 (2)0.7872 (2)0.0458 (8)
C70.5987 (6)0.3458 (3)0.7372 (2)0.0450 (8)
C80.9345 (6)0.2427 (2)0.6242 (2)0.0460 (8)
H80.78220.21540.59620.055*
C91.1764 (6)0.2611 (2)0.5350 (2)0.0452 (8)
C101.2679 (7)0.1803 (3)0.4708 (3)0.0636 (10)
H101.17970.11690.47990.076*
C111.4926 (8)0.1957 (3)0.3931 (3)0.0733 (11)
H111.55850.14260.34840.088*
C121.6179 (7)0.2890 (3)0.3819 (3)0.0633 (10)
H121.77080.30100.33000.076*
C131.5138 (7)0.3648 (3)0.4488 (3)0.0579 (9)
H131.59940.42870.44070.069*
C140.9002 (7)0.0734 (3)0.7220 (3)0.0559 (9)
C150.9784 (9)0.0099 (3)0.8176 (3)0.0692 (11)
F11.0325 (7)0.0896 (2)0.8000 (2)0.1305 (12)
F21.1921 (5)0.0454 (2)0.8518 (2)0.1161 (10)
F30.7729 (5)0.01262 (18)0.89643 (17)0.0900 (8)
N10.2992 (6)0.5696 (2)0.9241 (2)0.0577 (8)
N20.5252 (5)0.4407 (2)0.7824 (2)0.0501 (7)
H2A0.35500.44660.81290.060*
N30.8397 (5)0.33964 (18)0.67091 (18)0.0452 (7)
H3A0.93800.39400.65620.054*
N51.2952 (5)0.3525 (2)0.52564 (19)0.0498 (7)
O10.9029 (4)0.53802 (17)0.73670 (18)0.0626 (7)
O20.4438 (4)0.27274 (18)0.75907 (17)0.0589 (7)
O30.7370 (7)0.0374 (2)0.6769 (2)0.0951 (10)
N41.0171 (5)0.16519 (19)0.70160 (19)0.0465 (7)
H4A1.14510.17950.73490.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.068 (3)0.074 (3)0.063 (2)0.003 (2)0.013 (2)0.014 (2)
C20.086 (3)0.072 (3)0.064 (2)0.007 (2)0.003 (2)0.017 (2)
C30.098 (3)0.053 (2)0.096 (3)0.009 (2)0.007 (3)0.018 (2)
C40.070 (3)0.049 (2)0.077 (2)0.0077 (19)0.007 (2)0.0071 (19)
C50.0400 (18)0.0481 (19)0.0459 (18)0.0034 (14)0.0068 (15)0.0041 (15)
C60.0400 (18)0.0465 (19)0.0495 (18)0.0061 (15)0.0050 (15)0.0035 (15)
C70.0368 (17)0.053 (2)0.0453 (17)0.0108 (15)0.0037 (14)0.0062 (15)
C80.0420 (18)0.0485 (19)0.0481 (18)0.0115 (15)0.0060 (15)0.0048 (15)
C90.0402 (17)0.053 (2)0.0426 (17)0.0060 (15)0.0045 (14)0.0049 (15)
C100.062 (2)0.059 (2)0.067 (2)0.0132 (18)0.0066 (19)0.0184 (19)
C110.074 (3)0.071 (3)0.069 (2)0.004 (2)0.010 (2)0.027 (2)
C120.053 (2)0.081 (3)0.049 (2)0.002 (2)0.0065 (17)0.0028 (19)
C130.058 (2)0.057 (2)0.054 (2)0.0117 (17)0.0034 (18)0.0037 (17)
C140.055 (2)0.044 (2)0.065 (2)0.0169 (17)0.0071 (18)0.0126 (17)
C150.065 (3)0.046 (2)0.086 (3)0.0053 (18)0.013 (2)0.005 (2)
F10.183 (3)0.0577 (16)0.124 (2)0.0276 (17)0.029 (2)0.0120 (15)
F20.0781 (17)0.137 (2)0.130 (2)0.0238 (17)0.0312 (17)0.0656 (19)
F30.0847 (16)0.0973 (18)0.0740 (14)0.0032 (13)0.0174 (13)0.0100 (13)
N10.0540 (17)0.0597 (18)0.0555 (17)0.0041 (14)0.0033 (15)0.0075 (14)
N20.0329 (14)0.0559 (17)0.0579 (16)0.0078 (12)0.0075 (12)0.0121 (13)
N30.0413 (14)0.0388 (15)0.0531 (15)0.0104 (11)0.0019 (12)0.0045 (12)
N50.0517 (16)0.0494 (17)0.0463 (15)0.0111 (13)0.0003 (13)0.0035 (12)
O10.0431 (13)0.0553 (15)0.0817 (16)0.0120 (11)0.0143 (12)0.0073 (12)
O20.0443 (13)0.0639 (15)0.0688 (15)0.0240 (12)0.0002 (11)0.0126 (12)
O30.128 (3)0.0699 (19)0.095 (2)0.0560 (18)0.0221 (19)0.0104 (16)
N40.0425 (15)0.0467 (16)0.0505 (15)0.0136 (12)0.0048 (12)0.0035 (12)
Geometric parameters (Å, º) top
C1—N11.336 (4)C9—N51.323 (4)
C1—C21.365 (5)C9—C101.378 (4)
C1—H10.9300C10—C111.373 (5)
C2—C31.347 (5)C10—H100.9300
C2—H20.9300C11—C121.360 (5)
C3—C41.394 (5)C11—H110.9300
C3—H30.9300C12—C131.364 (5)
C4—C51.368 (5)C12—H120.9300
C4—H40.9300C13—N51.341 (4)
C5—N11.328 (4)C13—H130.9300
C5—C61.497 (4)C14—O31.205 (4)
C6—O11.218 (3)C14—N41.324 (4)
C6—N21.344 (4)C14—C151.535 (6)
C7—O21.224 (3)C15—F31.308 (4)
C7—N31.338 (4)C15—F11.308 (4)
C7—N21.384 (4)C15—F21.327 (5)
C8—N31.433 (4)N2—H2A0.8600
C8—N41.457 (4)N3—H3A0.8600
C8—C91.525 (4)N4—H4A0.8600
C8—H80.9800
N1—C1—C2123.4 (3)C11—C10—H10120.8
N1—C1—H1118.3C9—C10—H10120.8
C2—C1—H1118.3C12—C11—C10119.5 (3)
C3—C2—C1119.0 (4)C12—C11—H11120.3
C3—C2—H2120.5C10—C11—H11120.3
C1—C2—H2120.5C11—C12—C13118.3 (3)
C2—C3—C4119.1 (4)C11—C12—H12120.8
C2—C3—H3120.5C13—C12—H12120.8
C4—C3—H3120.5N5—C13—C12123.8 (3)
C5—C4—C3118.1 (3)N5—C13—H13118.1
C5—C4—H4121.0C12—C13—H13118.1
C3—C4—H4121.0O3—C14—N4127.6 (4)
N1—C5—C4123.3 (3)O3—C14—C15118.1 (3)
N1—C5—C6115.6 (3)N4—C14—C15114.3 (3)
C4—C5—C6121.0 (3)F3—C15—F1106.1 (3)
O1—C6—N2123.8 (3)F3—C15—F2105.4 (3)
O1—C6—C5122.7 (3)F1—C15—F2108.2 (4)
N2—C6—C5113.5 (2)F3—C15—C14110.8 (3)
O2—C7—N3123.5 (3)F1—C15—C14111.8 (4)
O2—C7—N2119.4 (3)F2—C15—C14114.1 (3)
N3—C7—N2117.1 (3)C5—N1—C1117.1 (3)
N3—C8—N4110.5 (2)C6—N2—C7131.5 (3)
N3—C8—C9110.3 (2)C6—N2—H2A114.3
N4—C8—C9110.2 (3)C7—N2—H2A114.3
N3—C8—H8108.6C7—N3—C8120.2 (2)
N4—C8—H8108.6C7—N3—H3A119.9
C9—C8—H8108.6C8—N3—H3A119.9
N5—C9—C10123.2 (3)C9—N5—C13116.8 (3)
N5—C9—C8118.2 (3)C14—N4—C8121.7 (3)
C10—C9—C8118.5 (3)C14—N4—H4A119.1
C11—C10—C9118.4 (3)C8—N4—H4A119.1
N1—C1—C2—C31.5 (6)N4—C14—C15—F1136.5 (3)
C1—C2—C3—C41.8 (7)O3—C14—C15—F2169.1 (3)
C2—C3—C4—C51.8 (6)N4—C14—C15—F213.3 (4)
C3—C4—C5—N11.5 (6)C4—C5—N1—C11.2 (5)
C3—C4—C5—C6178.4 (3)C6—C5—N1—C1178.2 (3)
N1—C5—C6—O1169.6 (3)C2—C1—N1—C51.2 (6)
C4—C5—C6—O17.5 (5)O1—C6—N2—C710.9 (6)
N1—C5—C6—N29.1 (4)C5—C6—N2—C7167.7 (3)
C4—C5—C6—N2173.8 (3)O2—C7—N2—C6166.5 (3)
N3—C8—C9—N512.3 (4)N3—C7—N2—C613.5 (5)
N4—C8—C9—N5110.0 (3)O2—C7—N3—C82.5 (5)
N3—C8—C9—C10170.3 (3)N2—C7—N3—C8177.6 (3)
N4—C8—C9—C1067.4 (4)N4—C8—N3—C770.4 (4)
N5—C9—C10—C110.3 (6)C9—C8—N3—C7167.5 (3)
C8—C9—C10—C11177.5 (3)C10—C9—N5—C130.3 (5)
C9—C10—C11—C120.2 (6)C8—C9—N5—C13177.6 (3)
C10—C11—C12—C130.3 (6)C12—C13—N5—C90.4 (5)
C11—C12—C13—N50.4 (6)O3—C14—N4—C86.9 (5)
O3—C14—C15—F372.2 (4)C15—C14—N4—C8170.4 (3)
N4—C14—C15—F3105.4 (3)N3—C8—N4—C14121.5 (3)
O3—C14—C15—F145.9 (5)C9—C8—N4—C14116.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N10.862.192.615 (4)111
N3—H3A···O10.862.162.781 (3)129
N4—H4A···O2i0.862.022.808 (3)151
Symmetry code: (i) x+1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds