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organic compounds
The title compound, C15H12F3N5O3, is a by-product isolated from the preparation of di-2-pyridiylglycoluril. The molecule contains two classical intramolecular N—HN and N—HO hydrogen bonds, and its crystal structure is stabilized mostly by intermolecular N—HO hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054109/bh2069sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054109/bh2069IIsup2.hkl |
CCDC reference: 633605
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
C15H12F3N5O3 | Z = 2 |
Mr = 367.30 | F(000) = 376 |
Triclinic, P1 | Dx = 1.520 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.9095 (12) Å | Cell parameters from 959 reflections |
b = 12.754 (3) Å | θ = 2.3–21.9° |
c = 13.072 (3) Å | µ = 0.13 mm−1 |
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 tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.0°, θmin = 1.6° |
φ and ω scans | h = −5→5 |
3937 measured reflections | k = −12→15 |
2775 independent reflections | l = −15→15 |
Refinement top
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H-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 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.1702 (8) | 0.6351 (3) | 0.9945 (3) | 0.0710 (11) | |
H1 | 0.0075 | 0.6143 | 1.0372 | 0.085* | |
C2 | 0.2648 (9) | 0.7311 (3) | 1.0071 (3) | 0.0754 (11) | |
H2 | 0.1705 | 0.7735 | 1.0583 | 0.090* | |
C3 | 0.4966 (9) | 0.7635 (3) | 0.9444 (3) | 0.0845 (13) | |
H3 | 0.5617 | 0.8294 | 0.9503 | 0.101* | |
C4 | 0.6375 (8) | 0.6968 (3) | 0.8704 (3) | 0.0673 (11) | |
H4 | 0.8009 | 0.7163 | 0.8273 | 0.081* | |
C5 | 0.5284 (6) | 0.6020 (2) | 0.8630 (2) | 0.0451 (8) | |
C6 | 0.6723 (6) | 0.5253 (2) | 0.7872 (2) | 0.0458 (8) | |
C7 | 0.5987 (6) | 0.3458 (3) | 0.7372 (2) | 0.0450 (8) | |
C8 | 0.9345 (6) | 0.2427 (2) | 0.6242 (2) | 0.0460 (8) | |
H8 | 0.7822 | 0.2154 | 0.5962 | 0.055* | |
C9 | 1.1764 (6) | 0.2611 (2) | 0.5350 (2) | 0.0452 (8) | |
C10 | 1.2679 (7) | 0.1803 (3) | 0.4708 (3) | 0.0636 (10) | |
H10 | 1.1797 | 0.1169 | 0.4799 | 0.076* | |
C11 | 1.4926 (8) | 0.1957 (3) | 0.3931 (3) | 0.0733 (11) | |
H11 | 1.5585 | 0.1426 | 0.3484 | 0.088* | |
C12 | 1.6179 (7) | 0.2890 (3) | 0.3819 (3) | 0.0633 (10) | |
H12 | 1.7708 | 0.3010 | 0.3300 | 0.076* | |
C13 | 1.5138 (7) | 0.3648 (3) | 0.4488 (3) | 0.0579 (9) | |
H13 | 1.5994 | 0.4287 | 0.4407 | 0.069* | |
C14 | 0.9002 (7) | 0.0734 (3) | 0.7220 (3) | 0.0559 (9) | |
C15 | 0.9784 (9) | 0.0099 (3) | 0.8176 (3) | 0.0692 (11) | |
F1 | 1.0325 (7) | −0.0896 (2) | 0.8000 (2) | 0.1305 (12) | |
F2 | 1.1921 (5) | 0.0454 (2) | 0.8518 (2) | 0.1161 (10) | |
F3 | 0.7729 (5) | 0.01262 (18) | 0.89643 (17) | 0.0900 (8) | |
N1 | 0.2992 (6) | 0.5696 (2) | 0.9241 (2) | 0.0577 (8) | |
N2 | 0.5252 (5) | 0.4407 (2) | 0.7824 (2) | 0.0501 (7) | |
H2A | 0.3550 | 0.4466 | 0.8129 | 0.060* | |
N3 | 0.8397 (5) | 0.33964 (18) | 0.67091 (18) | 0.0452 (7) | |
H3A | 0.9380 | 0.3940 | 0.6562 | 0.054* | |
N5 | 1.2952 (5) | 0.3525 (2) | 0.52564 (19) | 0.0498 (7) | |
O1 | 0.9029 (4) | 0.53802 (17) | 0.73670 (18) | 0.0626 (7) | |
O2 | 0.4438 (4) | 0.27274 (18) | 0.75907 (17) | 0.0589 (7) | |
O3 | 0.7370 (7) | 0.0374 (2) | 0.6769 (2) | 0.0951 (10) | |
N4 | 1.0171 (5) | 0.16519 (19) | 0.70160 (19) | 0.0465 (7) | |
H4A | 1.1451 | 0.1795 | 0.7349 | 0.056* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.068 (3) | 0.074 (3) | 0.063 (2) | −0.003 (2) | 0.013 (2) | −0.014 (2) |
C2 | 0.086 (3) | 0.072 (3) | 0.064 (2) | 0.007 (2) | −0.003 (2) | −0.017 (2) |
C3 | 0.098 (3) | 0.053 (2) | 0.096 (3) | −0.009 (2) | 0.007 (3) | −0.018 (2) |
C4 | 0.070 (3) | 0.049 (2) | 0.077 (2) | −0.0077 (19) | 0.007 (2) | −0.0071 (19) |
C5 | 0.0400 (18) | 0.0481 (19) | 0.0459 (18) | −0.0034 (14) | −0.0068 (15) | 0.0041 (15) |
C6 | 0.0400 (18) | 0.0465 (19) | 0.0495 (18) | −0.0061 (15) | −0.0050 (15) | 0.0035 (15) |
C7 | 0.0368 (17) | 0.053 (2) | 0.0453 (17) | −0.0108 (15) | −0.0037 (14) | −0.0062 (15) |
C8 | 0.0420 (18) | 0.0485 (19) | 0.0481 (18) | −0.0115 (15) | −0.0060 (15) | −0.0048 (15) |
C9 | 0.0402 (17) | 0.053 (2) | 0.0426 (17) | −0.0060 (15) | −0.0045 (14) | −0.0049 (15) |
C10 | 0.062 (2) | 0.059 (2) | 0.067 (2) | −0.0132 (18) | 0.0066 (19) | −0.0184 (19) |
C11 | 0.074 (3) | 0.071 (3) | 0.069 (2) | −0.004 (2) | 0.010 (2) | −0.027 (2) |
C12 | 0.053 (2) | 0.081 (3) | 0.049 (2) | −0.002 (2) | 0.0065 (17) | −0.0028 (19) |
C13 | 0.058 (2) | 0.057 (2) | 0.054 (2) | −0.0117 (17) | 0.0034 (18) | 0.0037 (17) |
C14 | 0.055 (2) | 0.044 (2) | 0.065 (2) | −0.0169 (17) | 0.0071 (18) | −0.0126 (17) |
C15 | 0.065 (3) | 0.046 (2) | 0.086 (3) | −0.0053 (18) | 0.013 (2) | 0.005 (2) |
F1 | 0.183 (3) | 0.0577 (16) | 0.124 (2) | 0.0276 (17) | 0.029 (2) | 0.0120 (15) |
F2 | 0.0781 (17) | 0.137 (2) | 0.130 (2) | −0.0238 (17) | −0.0312 (17) | 0.0656 (19) |
F3 | 0.0847 (16) | 0.0973 (18) | 0.0740 (14) | −0.0032 (13) | 0.0174 (13) | 0.0100 (13) |
N1 | 0.0540 (17) | 0.0597 (18) | 0.0555 (17) | −0.0041 (14) | 0.0033 (15) | −0.0075 (14) |
N2 | 0.0329 (14) | 0.0559 (17) | 0.0579 (16) | −0.0078 (12) | 0.0075 (12) | −0.0121 (13) |
N3 | 0.0413 (14) | 0.0388 (15) | 0.0531 (15) | −0.0104 (11) | 0.0019 (12) | −0.0045 (12) |
N5 | 0.0517 (16) | 0.0494 (17) | 0.0463 (15) | −0.0111 (13) | 0.0003 (13) | −0.0035 (12) |
O1 | 0.0431 (13) | 0.0553 (15) | 0.0817 (16) | −0.0120 (11) | 0.0143 (12) | −0.0073 (12) |
O2 | 0.0443 (13) | 0.0639 (15) | 0.0688 (15) | −0.0240 (12) | 0.0002 (11) | −0.0126 (12) |
O3 | 0.128 (3) | 0.0699 (19) | 0.095 (2) | −0.0560 (18) | −0.0221 (19) | −0.0104 (16) |
N4 | 0.0425 (15) | 0.0467 (16) | 0.0505 (15) | −0.0136 (12) | −0.0048 (12) | −0.0035 (12) |
Geometric parameters (Å, º) top
C1—N1 | 1.336 (4) | C9—N5 | 1.323 (4) |
C1—C2 | 1.365 (5) | C9—C10 | 1.378 (4) |
C1—H1 | 0.9300 | C10—C11 | 1.373 (5) |
C2—C3 | 1.347 (5) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C11—C12 | 1.360 (5) |
C3—C4 | 1.394 (5) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.364 (5) |
C4—C5 | 1.368 (5) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—N5 | 1.341 (4) |
C5—N1 | 1.328 (4) | C13—H13 | 0.9300 |
C5—C6 | 1.497 (4) | C14—O3 | 1.205 (4) |
C6—O1 | 1.218 (3) | C14—N4 | 1.324 (4) |
C6—N2 | 1.344 (4) | C14—C15 | 1.535 (6) |
C7—O2 | 1.224 (3) | C15—F3 | 1.308 (4) |
C7—N3 | 1.338 (4) | C15—F1 | 1.308 (4) |
C7—N2 | 1.384 (4) | C15—F2 | 1.327 (5) |
C8—N3 | 1.433 (4) | N2—H2A | 0.8600 |
C8—N4 | 1.457 (4) | N3—H3A | 0.8600 |
C8—C9 | 1.525 (4) | N4—H4A | 0.8600 |
C8—H8 | 0.9800 | ||
N1—C1—C2 | 123.4 (3) | C11—C10—H10 | 120.8 |
N1—C1—H1 | 118.3 | C9—C10—H10 | 120.8 |
C2—C1—H1 | 118.3 | C12—C11—C10 | 119.5 (3) |
C3—C2—C1 | 119.0 (4) | C12—C11—H11 | 120.3 |
C3—C2—H2 | 120.5 | C10—C11—H11 | 120.3 |
C1—C2—H2 | 120.5 | C11—C12—C13 | 118.3 (3) |
C2—C3—C4 | 119.1 (4) | C11—C12—H12 | 120.8 |
C2—C3—H3 | 120.5 | C13—C12—H12 | 120.8 |
C4—C3—H3 | 120.5 | N5—C13—C12 | 123.8 (3) |
C5—C4—C3 | 118.1 (3) | N5—C13—H13 | 118.1 |
C5—C4—H4 | 121.0 | C12—C13—H13 | 118.1 |
C3—C4—H4 | 121.0 | O3—C14—N4 | 127.6 (4) |
N1—C5—C4 | 123.3 (3) | O3—C14—C15 | 118.1 (3) |
N1—C5—C6 | 115.6 (3) | N4—C14—C15 | 114.3 (3) |
C4—C5—C6 | 121.0 (3) | F3—C15—F1 | 106.1 (3) |
O1—C6—N2 | 123.8 (3) | F3—C15—F2 | 105.4 (3) |
O1—C6—C5 | 122.7 (3) | F1—C15—F2 | 108.2 (4) |
N2—C6—C5 | 113.5 (2) | F3—C15—C14 | 110.8 (3) |
O2—C7—N3 | 123.5 (3) | F1—C15—C14 | 111.8 (4) |
O2—C7—N2 | 119.4 (3) | F2—C15—C14 | 114.1 (3) |
N3—C7—N2 | 117.1 (3) | C5—N1—C1 | 117.1 (3) |
N3—C8—N4 | 110.5 (2) | C6—N2—C7 | 131.5 (3) |
N3—C8—C9 | 110.3 (2) | C6—N2—H2A | 114.3 |
N4—C8—C9 | 110.2 (3) | C7—N2—H2A | 114.3 |
N3—C8—H8 | 108.6 | C7—N3—C8 | 120.2 (2) |
N4—C8—H8 | 108.6 | C7—N3—H3A | 119.9 |
C9—C8—H8 | 108.6 | C8—N3—H3A | 119.9 |
N5—C9—C10 | 123.2 (3) | C9—N5—C13 | 116.8 (3) |
N5—C9—C8 | 118.2 (3) | C14—N4—C8 | 121.7 (3) |
C10—C9—C8 | 118.5 (3) | C14—N4—H4A | 119.1 |
C11—C10—C9 | 118.4 (3) | C8—N4—H4A | 119.1 |
N1—C1—C2—C3 | 1.5 (6) | N4—C14—C15—F1 | −136.5 (3) |
C1—C2—C3—C4 | −1.8 (7) | O3—C14—C15—F2 | 169.1 (3) |
C2—C3—C4—C5 | 1.8 (6) | N4—C14—C15—F2 | −13.3 (4) |
C3—C4—C5—N1 | −1.5 (6) | C4—C5—N1—C1 | 1.2 (5) |
C3—C4—C5—C6 | −178.4 (3) | C6—C5—N1—C1 | 178.2 (3) |
N1—C5—C6—O1 | −169.6 (3) | C2—C1—N1—C5 | −1.2 (6) |
C4—C5—C6—O1 | 7.5 (5) | O1—C6—N2—C7 | 10.9 (6) |
N1—C5—C6—N2 | 9.1 (4) | C5—C6—N2—C7 | −167.7 (3) |
C4—C5—C6—N2 | −173.8 (3) | O2—C7—N2—C6 | 166.5 (3) |
N3—C8—C9—N5 | 12.3 (4) | N3—C7—N2—C6 | −13.5 (5) |
N4—C8—C9—N5 | −110.0 (3) | O2—C7—N3—C8 | −2.5 (5) |
N3—C8—C9—C10 | −170.3 (3) | N2—C7—N3—C8 | 177.6 (3) |
N4—C8—C9—C10 | 67.4 (4) | N4—C8—N3—C7 | −70.4 (4) |
N5—C9—C10—C11 | −0.3 (6) | C9—C8—N3—C7 | 167.5 (3) |
C8—C9—C10—C11 | −177.5 (3) | C10—C9—N5—C13 | 0.3 (5) |
C9—C10—C11—C12 | 0.2 (6) | C8—C9—N5—C13 | 177.6 (3) |
C10—C11—C12—C13 | −0.3 (6) | C12—C13—N5—C9 | −0.4 (5) |
C11—C12—C13—N5 | 0.4 (6) | O3—C14—N4—C8 | 6.9 (5) |
O3—C14—C15—F3 | −72.2 (4) | C15—C14—N4—C8 | −170.4 (3) |
N4—C14—C15—F3 | 105.4 (3) | N3—C8—N4—C14 | 121.5 (3) |
O3—C14—C15—F1 | 45.9 (5) | C9—C8—N4—C14 | −116.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1 | 0.86 | 2.19 | 2.615 (4) | 111 |
N3—H3A···O1 | 0.86 | 2.16 | 2.781 (3) | 129 |
N4—H4A···O2i | 0.86 | 2.02 | 2.808 (3) | 151 |
Symmetry code: (i) x+1, y, z. |
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