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The title compound, C10H7FN2O2, was synthesized by the reaction of 4-fluoro­benzaldehyde and imidazolidine-2,4-dione under microwave irradiation. In the crystal structure, there are inter­molecular N—H...O hydrogen bonds and weak π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024104/ww6390sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024104/ww6390Isup2.hkl
Contains datablock I

CCDC reference: 284002

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.040
  • wR factor = 0.114
  • Data-to-parameter ratio = 6.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . !
Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.89 Sigma PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.79 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K 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 25.96 From the CIF: _reflns_number_total 985 Count of symmetry unique reflns 966 Completeness (_total/calc) 101.97% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 19 Fraction of Friedel pairs measured 0.020 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: PLATON (Spek, 2003).

5-(4-Fluorobenzylidene)imidazolidine-2,4-dione top
Crystal data top
C10H7FN2O2F(000) = 212
Mr = 206.18Dx = 1.517 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 3.8250 (8) Åθ = 9–12°
b = 6.2410 (12) ŵ = 0.12 mm1
c = 18.988 (4) ÅT = 293 K
β = 95.25 (3)°Sheet, light yellow
V = 451.38 (16) Å30.3 × 0.2 × 0.1 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.018
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 1.1°
Graphite monochromatorh = 04
ω/2θ scansk = 17
1155 measured reflectionsl = 2222
985 independent reflections3 standard reflections every 200 reflections
806 reflections with I > 2σ(I) intensity decay: none
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)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.064P)2 + 0.038P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
985 reflectionsΔρmax = 0.18 e Å3
145 parametersΔρmin = 0.16 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (9)
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
F1.3552 (7)0.3128 (6)0.44119 (13)0.0854 (12)
O20.4354 (9)0.6359 (5)0.16225 (15)0.0572 (9)
O10.1868 (8)0.0370 (5)0.02950 (14)0.0617 (9)
C100.5661 (8)0.2600 (6)0.18368 (17)0.0315 (7)
N10.4905 (9)0.0875 (5)0.13867 (16)0.0379 (7)
N20.2659 (8)0.3724 (6)0.08143 (16)0.0412 (8)
C11.1995 (10)0.1685 (8)0.3937 (2)0.0514 (12)
C21.1545 (9)0.2264 (8)0.3244 (2)0.0485 (9)
H2B1.23000.35940.30970.058*
C30.9949 (9)0.0836 (6)0.27647 (18)0.0376 (8)
H3A0.96100.12110.22890.045*
C40.8826 (8)0.1173 (6)0.29826 (17)0.0348 (8)
C50.9381 (10)0.1679 (7)0.36921 (18)0.0462 (10)
H5A0.86750.30120.38470.055*
C61.0964 (11)0.0248 (10)0.41768 (19)0.0592 (12)
H6A1.13140.05970.46540.071*
C70.7229 (8)0.2774 (6)0.24941 (17)0.0353 (7)
H7A0.73150.41650.26710.042*
C80.3013 (10)0.1501 (6)0.07797 (18)0.0395 (9)
C90.4189 (10)0.4490 (6)0.1435 (2)0.0378 (8)
H20.141 (10)0.437 (8)0.0468 (18)0.046 (12)*
H10.507 (10)0.041 (7)0.1497 (19)0.034 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F0.081 (2)0.089 (3)0.0805 (19)0.0062 (17)0.0233 (15)0.0459 (19)
O20.083 (2)0.0242 (14)0.0613 (18)0.0020 (15)0.0125 (16)0.0016 (14)
O10.083 (2)0.0479 (18)0.0492 (14)0.0019 (18)0.0219 (15)0.0116 (15)
C100.0336 (16)0.0228 (15)0.0378 (16)0.0009 (16)0.0013 (13)0.0002 (15)
N10.0511 (18)0.0222 (16)0.0383 (14)0.0009 (14)0.0080 (13)0.0008 (13)
N20.0497 (19)0.0322 (17)0.0401 (18)0.0021 (16)0.0050 (15)0.0084 (15)
C10.0369 (18)0.063 (3)0.051 (2)0.0042 (19)0.0115 (17)0.023 (2)
C20.0404 (19)0.043 (2)0.060 (2)0.000 (2)0.0032 (17)0.005 (2)
C30.0338 (17)0.037 (2)0.0402 (18)0.0022 (16)0.0062 (14)0.0028 (16)
C40.0294 (15)0.0373 (19)0.0366 (15)0.0072 (16)0.0032 (13)0.0019 (17)
C50.0447 (19)0.052 (2)0.0406 (18)0.0015 (19)0.0060 (17)0.0027 (18)
C60.056 (2)0.085 (3)0.0345 (19)0.004 (3)0.0057 (18)0.008 (2)
C70.0365 (17)0.0289 (16)0.0392 (17)0.0014 (17)0.0026 (14)0.0068 (17)
C80.043 (2)0.035 (2)0.039 (2)0.0015 (17)0.0078 (16)0.0017 (17)
C90.044 (2)0.0242 (17)0.0445 (19)0.0002 (16)0.0005 (16)0.0047 (16)
Geometric parameters (Å, º) top
F—C11.371 (5)C1—C61.360 (8)
O2—C91.220 (5)C2—C31.376 (5)
O1—C81.209 (4)C2—H2B0.9300
C10—C71.339 (4)C3—C41.400 (5)
C10—N11.388 (5)C3—H3A0.9300
C10—C91.487 (5)C4—C51.381 (5)
N1—C81.361 (5)C4—C71.459 (5)
N1—H10.83 (4)C5—C61.382 (6)
N2—C91.354 (5)C5—H5A0.9300
N2—C81.396 (5)C6—H6A0.9300
N2—H20.88 (4)C7—H7A0.9300
C1—C21.361 (6)
C7—C10—N1133.4 (3)C5—C4—C3118.0 (4)
C7—C10—C9122.0 (3)C5—C4—C7118.8 (4)
N1—C10—C9104.5 (3)C3—C4—C7123.2 (3)
C8—N1—C10111.3 (3)C4—C5—C6121.4 (4)
C8—N1—H1121 (3)C4—C5—H5A119.3
C10—N1—H1126 (3)C6—C5—H5A119.3
C9—N2—C8111.0 (3)C1—C6—C5118.2 (4)
C9—N2—H2131 (3)C1—C6—H6A120.9
C8—N2—H2118 (3)C5—C6—H6A120.9
C2—C1—C6123.0 (4)C10—C7—C4131.5 (4)
C2—C1—F118.0 (5)C10—C7—H7A114.2
C6—C1—F119.0 (4)C4—C7—H7A114.2
C1—C2—C3118.5 (4)O1—C8—N1127.2 (4)
C1—C2—H2B120.8O1—C8—N2125.9 (4)
C3—C2—H2B120.8N1—C8—N2107.0 (3)
C2—C3—C4120.9 (3)O2—C9—N2126.8 (4)
C2—C3—H3A119.5O2—C9—C10127.0 (4)
C4—C3—H3A119.5N2—C9—C10106.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.83 (4)2.05 (4)2.865 (4)166 (4)
N2—H2···O1ii0.88 (4)1.93 (4)2.797 (4)170 (5)
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z.
 

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