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In the title compound, C14H12F2N4O4, an intra­molecular N—H...N hydrogen bond forms a six-membered ring within the urea bridge.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021684/bi2017sup1.cif
Contains datablocks global, 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021684/bi20174sup2.hkl
Contains datablock 4

CCDC reference: 293796

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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
C14H12F2N4O4F(000) = 696
Mr = 338.28Dx = 1.487 Mg m3
Monoclinic, CcMelting point: 433 K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71073 Å
a = 7.6870 (8) ÅCell parameters from 2565 reflections
b = 31.097 (3) Åθ = 2.6–22.7°
c = 6.7432 (7) ŵ = 0.13 mm1
β = 110.371 (2)°T = 298 K
V = 1511.1 (3) Å3Block, colourless
Z = 40.22 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD
diffractometer
Rint = 0.054
Graphite monochromatorθmax = 28.3°, θmin = 1.3°
φ and ω scansh = 1010
6669 measured reflectionsk = 3940
1809 independent reflectionsl = 88
1314 reflections with I > 2σ(I)
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)] = 0.036H-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 reflectionsΔρmax = 0.22 e Å3
218 parametersΔρmin = 0.18 e Å3
2 restraintsExtinction correction: Larson (1970), equation 22
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.6 (1) x 102
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
H10.67960.29960.16020.1015*
H20.73550.25330.45140.1204*
H30.53870.25050.65010.1288*
H40.07000.40870.25590.0596*
H50.40610.47830.39050.0552*
H60.00810.65860.16410.0974*
H70.14240.62680.23650.0968*
H80.13550.62480.00420.0975*
H90.24880.56030.05980.0507*
H100.31420.42550.16180.0783*
H110.29130.42230.07310.0785*
H120.49010.42920.05230.0786*
F10.2445 (5)0.29571 (11)0.5686 (6)0.1221
F20.4132 (4)0.35240 (9)0.0240 (5)0.0942
N10.1678 (3)0.39627 (9)0.2471 (5)0.0503
N20.3015 (3)0.46410 (8)0.3276 (4)0.0478
N30.1810 (3)0.53158 (8)0.2666 (4)0.0460
N40.0213 (3)0.47079 (8)0.1641 (4)0.0398
O10.0018 (3)0.33619 (8)0.1626 (6)0.0799
O20.4776 (3)0.40524 (8)0.4314 (5)0.0672
O30.0784 (3)0.59901 (7)0.2153 (4)0.0622
O40.3355 (3)0.48182 (7)0.0111 (4)0.0512
C10.3254 (4)0.32529 (10)0.2968 (6)0.0560
C20.4464 (5)0.32528 (11)0.1857 (7)0.0670
C30.5986 (6)0.29892 (13)0.2371 (9)0.0858
C40.6306 (7)0.27167 (15)0.4058 (11)0.1068
C50.5146 (8)0.26973 (16)0.5202 (10)0.1071
C60.3615 (6)0.29682 (14)0.4598 (8)0.0810
C70.1527 (5)0.35227 (11)0.2319 (6)0.0561
C80.3263 (4)0.42028 (10)0.3421 (5)0.0473
C90.1452 (4)0.48979 (9)0.2484 (5)0.0407
C100.0331 (4)0.55731 (9)0.1936 (5)0.0439
C110.1461 (4)0.54186 (9)0.1053 (4)0.0429
C120.1639 (4)0.49782 (10)0.0953 (4)0.0409
C130.0678 (5)0.63017 (11)0.1399 (7)0.0662
C140.3610 (4)0.43589 (10)0.0030 (6)0.0533
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.129 (3)0.113 (2)0.147 (3)0.029 (2)0.077 (2)0.054 (2)
F20.0900 (19)0.0882 (18)0.119 (2)0.0144 (15)0.0545 (17)0.0229 (16)
N10.0306 (12)0.0447 (13)0.0703 (18)0.0002 (10)0.0107 (12)0.0014 (13)
N20.0284 (12)0.0430 (13)0.0649 (18)0.0042 (10)0.0071 (11)0.0044 (12)
N30.0335 (12)0.0464 (13)0.0524 (16)0.0035 (10)0.0079 (11)0.0020 (11)
N40.0282 (10)0.0426 (12)0.0457 (12)0.0019 (9)0.0093 (9)0.0011 (11)
O10.0413 (13)0.0552 (15)0.133 (3)0.0109 (11)0.0168 (14)0.0088 (17)
O20.0347 (12)0.0479 (13)0.102 (2)0.0053 (9)0.0023 (12)0.0012 (13)
O30.0465 (12)0.0424 (11)0.0867 (18)0.0025 (10)0.0093 (12)0.0014 (11)
O40.0283 (9)0.0468 (11)0.0701 (14)0.0010 (8)0.0062 (9)0.0018 (10)
C10.0423 (16)0.0361 (14)0.084 (2)0.0014 (12)0.0144 (16)0.0014 (15)
C20.055 (2)0.0446 (17)0.099 (3)0.0039 (15)0.0237 (19)0.0012 (19)
C30.063 (2)0.061 (2)0.139 (4)0.008 (2)0.042 (3)0.011 (3)
C40.074 (3)0.064 (3)0.170 (6)0.027 (2)0.026 (4)0.009 (3)
C50.099 (4)0.073 (3)0.141 (5)0.028 (3)0.031 (4)0.036 (3)
C60.073 (3)0.060 (2)0.111 (4)0.009 (2)0.033 (3)0.018 (2)
C70.0404 (15)0.0459 (16)0.078 (2)0.0018 (13)0.0156 (15)0.0009 (16)
C80.0348 (14)0.0428 (15)0.0598 (19)0.0013 (12)0.0108 (13)0.0033 (15)
C90.0330 (13)0.0457 (15)0.0413 (14)0.0023 (11)0.0104 (11)0.0011 (12)
C100.0413 (15)0.0427 (15)0.0445 (15)0.0014 (11)0.0109 (12)0.0013 (12)
C110.0354 (13)0.0429 (15)0.0476 (16)0.0068 (11)0.0108 (12)0.0050 (12)
C120.0311 (12)0.0499 (15)0.0405 (14)0.0006 (11)0.0109 (11)0.0015 (13)
C130.058 (2)0.0450 (17)0.090 (3)0.0027 (15)0.019 (2)0.0055 (18)
C140.0334 (15)0.0487 (17)0.072 (2)0.0052 (13)0.0117 (14)0.0001 (15)
Geometric parameters (Å, º) top
H1—C30.940N3—C101.336 (4)
H2—C40.947N4—C91.343 (3)
H3—C51.023N4—C121.330 (3)
H4—N10.866O1—C71.199 (4)
H5—N20.886O2—C81.203 (4)
H6—C130.984O3—C101.337 (3)
H7—C131.012O3—C131.436 (4)
H8—C130.944O4—C121.338 (3)
H9—C110.937O4—C141.440 (4)
H10—C141.054C1—C21.383 (5)
H11—C140.960C1—C61.362 (6)
H12—C140.954C1—C71.501 (5)
F1—C61.344 (6)C2—C31.370 (5)
F2—C21.331 (5)C3—C41.370 (8)
N1—C71.374 (4)C4—C51.369 (8)
N1—C81.381 (4)C5—C61.388 (6)
N2—C81.375 (4)C10—C111.382 (4)
N2—C91.386 (4)C11—C121.376 (4)
N3—C91.325 (4)
H4—N1—C7113.4C1—C7—O1121.2 (3)
H4—N1—C8111.9N1—C7—O1119.3 (3)
C7—N1—C8127.6 (3)N1—C8—N2115.1 (3)
H5—N2—C8112.4N1—C8—O2124.4 (3)
H5—N2—C9114.7N2—C8—O2120.5 (3)
C8—N2—C9132.8 (3)N2—C9—N4118.7 (3)
C9—N3—C10115.5 (2)N2—C9—N3113.9 (3)
C9—N4—C12114.7 (2)N4—C9—N3127.4 (3)
C10—O3—C13118.3 (2)O3—C10—N3112.6 (2)
C12—O4—C14119.1 (2)O3—C10—C11124.5 (3)
C2—C1—C6116.8 (4)N3—C10—C11122.9 (3)
C2—C1—C7122.3 (4)H9—C11—C10121.9
C6—C1—C7120.6 (4)H9—C11—C12122.4
C1—C2—F2118.1 (3)C10—C11—C12115.7 (2)
C1—C2—C3122.6 (4)C11—C12—O4117.2 (3)
F2—C2—C3119.3 (4)C11—C12—N4123.8 (3)
H1—C3—C2121.2O4—C12—N4119.0 (3)
H1—C3—C4120.6H7—C13—O3104.5
C2—C3—C4118.1 (5)H7—C13—H6108.8
H2—C4—C3121.9O3—C13—H6106.6
H2—C4—C5116.0H7—C13—H8114.3
C3—C4—C5122.1 (4)O3—C13—H8109.2
H3—C5—C4123.3H6—C13—H8112.8
H3—C5—C6119.3H10—C14—O4105.7
C4—C5—C6117.4 (5)H10—C14—H11110.6
C5—C6—F1118.9 (5)O4—C14—H11111.3
C5—C6—C1123.0 (5)H10—C14—H12105.7
F1—C6—C1118.0 (4)O4—C14—H12109.9
C1—C7—N1119.5 (3)H11—C14—H12113.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H4···N40.872.072.689 (3)127
 

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