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organic compounds
In the title compound, C14H12F2N4O4, an intramolecular N—HN hydrogen bond forms a six-membered ring within the urea bridge.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021684/bi2017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021684/bi20174sup2.hkl |
CCDC reference: 293796
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.036
- wR factor = 0.075
- Data-to-parameter ratio = 8.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.63 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.29 From the CIF: _reflns_number_total 1809 Count of symmetry unique reflns 1875 Completeness (_total/calc) 96.48% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1993); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: CRYSTALS.
N-(2,6-Difluorobenzoyl)-N'-(4,6-dimethoxypyrimidin-2-yl)urea top
Crystal data top
C14H12F2N4O4 | F(000) = 696 |
Mr = 338.28 | Dx = 1.487 Mg m−3 |
Monoclinic, Cc | Melting point: 433 K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6870 (8) Å | Cell parameters from 2565 reflections |
b = 31.097 (3) Å | θ = 2.6–22.7° |
c = 6.7432 (7) Å | µ = 0.13 mm−1 |
β = 110.371 (2)° | T = 298 K |
V = 1511.1 (3) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.20 × 0.18 mm |
Data collection top
Bruker SMART CCD diffractometer | Rint = 0.054 |
Graphite monochromator | θmax = 28.3°, θmin = 1.3° |
φ and ω scans | h = −10→10 |
6669 measured reflections | k = −39→40 |
1809 independent reflections | l = −8→8 |
1314 reflections with I > 2σ(I) |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.075 | w = [1 - (Fo - Fc)2/36σ2(F)]2/
[7.65T0(x) + 9.99T1(x) + 2.89T2(x)],
where Ti are the Chebychev polynomials and x = Fc/Fmax (Prince, 1982; Watkin, 1994) |
S = 0.96 | (Δ/σ)max = 0.000314 |
1801 reflections | Δρmax = 0.22 e Å−3 |
218 parameters | Δρmin = −0.18 e Å−3 |
2 restraints | Extinction correction: Larson (1970), equation 22 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.6 (1) x 102 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
H1 | 0.6796 | 0.2996 | 0.1602 | 0.1015* | |
H2 | 0.7355 | 0.2533 | 0.4514 | 0.1204* | |
H3 | 0.5387 | 0.2505 | 0.6501 | 0.1288* | |
H4 | 0.0700 | 0.4087 | 0.2559 | 0.0596* | |
H5 | 0.4061 | 0.4783 | 0.3905 | 0.0552* | |
H6 | −0.0081 | 0.6586 | 0.1641 | 0.0974* | |
H7 | −0.1424 | 0.6268 | 0.2365 | 0.0968* | |
H8 | −0.1355 | 0.6248 | −0.0042 | 0.0975* | |
H9 | −0.2488 | 0.5603 | 0.0598 | 0.0507* | |
H10 | −0.3142 | 0.4255 | 0.1618 | 0.0783* | |
H11 | −0.2913 | 0.4223 | −0.0731 | 0.0785* | |
H12 | −0.4901 | 0.4292 | −0.0523 | 0.0786* | |
F1 | 0.2445 (5) | 0.29571 (11) | 0.5686 (6) | 0.1221 | |
F2 | 0.4132 (4) | 0.35240 (9) | 0.0240 (5) | 0.0942 | |
N1 | 0.1678 (3) | 0.39627 (9) | 0.2471 (5) | 0.0503 | |
N2 | 0.3015 (3) | 0.46410 (8) | 0.3276 (4) | 0.0478 | |
N3 | 0.1810 (3) | 0.53158 (8) | 0.2666 (4) | 0.0460 | |
N4 | −0.0213 (3) | 0.47079 (8) | 0.1641 (4) | 0.0398 | |
O1 | 0.0018 (3) | 0.33619 (8) | 0.1626 (6) | 0.0799 | |
O2 | 0.4776 (3) | 0.40524 (8) | 0.4314 (5) | 0.0672 | |
O3 | 0.0784 (3) | 0.59901 (7) | 0.2153 (4) | 0.0622 | |
O4 | −0.3355 (3) | 0.48182 (7) | 0.0111 (4) | 0.0512 | |
C1 | 0.3254 (4) | 0.32529 (10) | 0.2968 (6) | 0.0560 | |
C2 | 0.4464 (5) | 0.32528 (11) | 0.1857 (7) | 0.0670 | |
C3 | 0.5986 (6) | 0.29892 (13) | 0.2371 (9) | 0.0858 | |
C4 | 0.6306 (7) | 0.27167 (15) | 0.4058 (11) | 0.1068 | |
C5 | 0.5146 (8) | 0.26973 (16) | 0.5202 (10) | 0.1071 | |
C6 | 0.3615 (6) | 0.29682 (14) | 0.4598 (8) | 0.0810 | |
C7 | 0.1527 (5) | 0.35227 (11) | 0.2319 (6) | 0.0561 | |
C8 | 0.3263 (4) | 0.42028 (10) | 0.3421 (5) | 0.0473 | |
C9 | 0.1452 (4) | 0.48979 (9) | 0.2484 (5) | 0.0407 | |
C10 | 0.0331 (4) | 0.55731 (9) | 0.1936 (5) | 0.0439 | |
C11 | −0.1461 (4) | 0.54186 (9) | 0.1053 (4) | 0.0429 | |
C12 | −0.1639 (4) | 0.49782 (10) | 0.0953 (4) | 0.0409 | |
C13 | −0.0678 (5) | 0.63017 (11) | 0.1399 (7) | 0.0662 | |
C14 | −0.3610 (4) | 0.43589 (10) | 0.0030 (6) | 0.0533 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.129 (3) | 0.113 (2) | 0.147 (3) | 0.029 (2) | 0.077 (2) | 0.054 (2) |
F2 | 0.0900 (19) | 0.0882 (18) | 0.119 (2) | 0.0144 (15) | 0.0545 (17) | 0.0229 (16) |
N1 | 0.0306 (12) | 0.0447 (13) | 0.0703 (18) | −0.0002 (10) | 0.0107 (12) | −0.0014 (13) |
N2 | 0.0284 (12) | 0.0430 (13) | 0.0649 (18) | −0.0042 (10) | 0.0071 (11) | −0.0044 (12) |
N3 | 0.0335 (12) | 0.0464 (13) | 0.0524 (16) | −0.0035 (10) | 0.0079 (11) | −0.0020 (11) |
N4 | 0.0282 (10) | 0.0426 (12) | 0.0457 (12) | −0.0019 (9) | 0.0093 (9) | −0.0011 (11) |
O1 | 0.0413 (13) | 0.0552 (15) | 0.133 (3) | −0.0109 (11) | 0.0168 (14) | −0.0088 (17) |
O2 | 0.0347 (12) | 0.0479 (13) | 0.102 (2) | 0.0053 (9) | 0.0023 (12) | −0.0012 (13) |
O3 | 0.0465 (12) | 0.0424 (11) | 0.0867 (18) | −0.0025 (10) | 0.0093 (12) | 0.0014 (11) |
O4 | 0.0283 (9) | 0.0468 (11) | 0.0701 (14) | −0.0010 (8) | 0.0062 (9) | 0.0018 (10) |
C1 | 0.0423 (16) | 0.0361 (14) | 0.084 (2) | −0.0014 (12) | 0.0144 (16) | 0.0014 (15) |
C2 | 0.055 (2) | 0.0446 (17) | 0.099 (3) | −0.0039 (15) | 0.0237 (19) | −0.0012 (19) |
C3 | 0.063 (2) | 0.061 (2) | 0.139 (4) | 0.008 (2) | 0.042 (3) | −0.011 (3) |
C4 | 0.074 (3) | 0.064 (3) | 0.170 (6) | 0.027 (2) | 0.026 (4) | 0.009 (3) |
C5 | 0.099 (4) | 0.073 (3) | 0.141 (5) | 0.028 (3) | 0.031 (4) | 0.036 (3) |
C6 | 0.073 (3) | 0.060 (2) | 0.111 (4) | 0.009 (2) | 0.033 (3) | 0.018 (2) |
C7 | 0.0404 (15) | 0.0459 (16) | 0.078 (2) | −0.0018 (13) | 0.0156 (15) | −0.0009 (16) |
C8 | 0.0348 (14) | 0.0428 (15) | 0.0598 (19) | 0.0013 (12) | 0.0108 (13) | −0.0033 (15) |
C9 | 0.0330 (13) | 0.0457 (15) | 0.0413 (14) | 0.0023 (11) | 0.0104 (11) | −0.0011 (12) |
C10 | 0.0413 (15) | 0.0427 (15) | 0.0445 (15) | −0.0014 (11) | 0.0109 (12) | −0.0013 (12) |
C11 | 0.0354 (13) | 0.0429 (15) | 0.0476 (16) | 0.0068 (11) | 0.0108 (12) | 0.0050 (12) |
C12 | 0.0311 (12) | 0.0499 (15) | 0.0405 (14) | −0.0006 (11) | 0.0109 (11) | −0.0015 (13) |
C13 | 0.058 (2) | 0.0450 (17) | 0.090 (3) | 0.0027 (15) | 0.019 (2) | 0.0055 (18) |
C14 | 0.0334 (15) | 0.0487 (17) | 0.072 (2) | −0.0052 (13) | 0.0117 (14) | 0.0001 (15) |
Geometric parameters (Å, º) top
H1—C3 | 0.940 | N3—C10 | 1.336 (4) |
H2—C4 | 0.947 | N4—C9 | 1.343 (3) |
H3—C5 | 1.023 | N4—C12 | 1.330 (3) |
H4—N1 | 0.866 | O1—C7 | 1.199 (4) |
H5—N2 | 0.886 | O2—C8 | 1.203 (4) |
H6—C13 | 0.984 | O3—C10 | 1.337 (3) |
H7—C13 | 1.012 | O3—C13 | 1.436 (4) |
H8—C13 | 0.944 | O4—C12 | 1.338 (3) |
H9—C11 | 0.937 | O4—C14 | 1.440 (4) |
H10—C14 | 1.054 | C1—C2 | 1.383 (5) |
H11—C14 | 0.960 | C1—C6 | 1.362 (6) |
H12—C14 | 0.954 | C1—C7 | 1.501 (5) |
F1—C6 | 1.344 (6) | C2—C3 | 1.370 (5) |
F2—C2 | 1.331 (5) | C3—C4 | 1.370 (8) |
N1—C7 | 1.374 (4) | C4—C5 | 1.369 (8) |
N1—C8 | 1.381 (4) | C5—C6 | 1.388 (6) |
N2—C8 | 1.375 (4) | C10—C11 | 1.382 (4) |
N2—C9 | 1.386 (4) | C11—C12 | 1.376 (4) |
N3—C9 | 1.325 (4) | ||
H4—N1—C7 | 113.4 | C1—C7—O1 | 121.2 (3) |
H4—N1—C8 | 111.9 | N1—C7—O1 | 119.3 (3) |
C7—N1—C8 | 127.6 (3) | N1—C8—N2 | 115.1 (3) |
H5—N2—C8 | 112.4 | N1—C8—O2 | 124.4 (3) |
H5—N2—C9 | 114.7 | N2—C8—O2 | 120.5 (3) |
C8—N2—C9 | 132.8 (3) | N2—C9—N4 | 118.7 (3) |
C9—N3—C10 | 115.5 (2) | N2—C9—N3 | 113.9 (3) |
C9—N4—C12 | 114.7 (2) | N4—C9—N3 | 127.4 (3) |
C10—O3—C13 | 118.3 (2) | O3—C10—N3 | 112.6 (2) |
C12—O4—C14 | 119.1 (2) | O3—C10—C11 | 124.5 (3) |
C2—C1—C6 | 116.8 (4) | N3—C10—C11 | 122.9 (3) |
C2—C1—C7 | 122.3 (4) | H9—C11—C10 | 121.9 |
C6—C1—C7 | 120.6 (4) | H9—C11—C12 | 122.4 |
C1—C2—F2 | 118.1 (3) | C10—C11—C12 | 115.7 (2) |
C1—C2—C3 | 122.6 (4) | C11—C12—O4 | 117.2 (3) |
F2—C2—C3 | 119.3 (4) | C11—C12—N4 | 123.8 (3) |
H1—C3—C2 | 121.2 | O4—C12—N4 | 119.0 (3) |
H1—C3—C4 | 120.6 | H7—C13—O3 | 104.5 |
C2—C3—C4 | 118.1 (5) | H7—C13—H6 | 108.8 |
H2—C4—C3 | 121.9 | O3—C13—H6 | 106.6 |
H2—C4—C5 | 116.0 | H7—C13—H8 | 114.3 |
C3—C4—C5 | 122.1 (4) | O3—C13—H8 | 109.2 |
H3—C5—C4 | 123.3 | H6—C13—H8 | 112.8 |
H3—C5—C6 | 119.3 | H10—C14—O4 | 105.7 |
C4—C5—C6 | 117.4 (5) | H10—C14—H11 | 110.6 |
C5—C6—F1 | 118.9 (5) | O4—C14—H11 | 111.3 |
C5—C6—C1 | 123.0 (5) | H10—C14—H12 | 105.7 |
F1—C6—C1 | 118.0 (4) | O4—C14—H12 | 109.9 |
C1—C7—N1 | 119.5 (3) | H11—C14—H12 | 113.2 |
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