Literature DB >> 24860383

6-Fluoro-4-oxo-4H-chromene-3-carbalde-hyde.

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H5FO3, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.0071 Å), with the largest deviation from the mean plane [0.0203 (15) Å] being found for the ring C atom in the 2-position. In the crystal, mol-ecules are linked into a three-dimensional architecture via C-H⋯O hydrogen bonds and π-π stacking inter-actions between the chromone units along the a-axis direction [centroid-centroid distance between the benzene and pyran rings = 3.707 (2) Å].

Entities:  

Year:  2014        PMID： 24860383      PMCID： PMC4011281          DOI： 10.1107/S1600536814008502

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Ishikawa (2014a ▶,b ▶). For halogen bonding, see: Auffinger et al. (2004 ▶); Metrangolo et al. (2005 ▶); Wilcken et al. (2013 ▶); Sirimulla et al. (2013 ▶).

Experimental

Crystal data

C10H5FO3 M = 192.15 Monoclinic, a = 7.8530 (19) Å b = 5.6020 (17) Å c = 17.987 (5) Å β = 95.09 (2)° V = 788.2 (4) Å3 Z = 4 Mo Kα radiation μ = 0.14 mm−1 T = 100 K 0.30 × 0.20 × 0.12 mm

Data collection

Rigaku AFC-7R diffractometer 2412 measured reflections 1815 independent reflections 1496 reflections with F 2 > 2σ(F 2) R int = 0.024 3 standard reflections every 150 reflections intensity decay: 3.4%

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.106 S = 1.03 1815 reflections 128 parameters H-atom parameters constrained Δρmax = 0.37 e Å−3 Δρmin = −0.22 e Å−3 Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 ▶); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SIR2008 (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure. Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536814008502/tk5307sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008502/tk5307Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814008502/tk5307Isup3.cml CCDC reference: 997449 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H5FO3F(000) = 392.00
Mr = 192.15Dx = 1.619 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 7.8530 (19) Åθ = 15.2–17.3°
b = 5.6020 (17) ŵ = 0.14 mm−1
c = 17.987 (5) ÅT = 100 K
β = 95.09 (2)°Plate, colourless
V = 788.2 (4) Å30.30 × 0.20 × 0.12 mm
Z = 4
Rigaku AFC-7R diffractometerθmax = 27.5°
ω–2θ scansh = −10→10
2412 measured reflectionsk = −4→7
1815 independent reflectionsl = −23→13
1496 reflections with F2 > 2σ(F2)3 standard reflections every 150 reflections
Rint = 0.024 intensity decay: 3.4%
Refinement on F2Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.106w = 1/[σ2(Fo2) + (0.0562P)2 + 0.3686P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1815 reflectionsΔρmax = 0.37 e Å−3
128 parametersΔρmin = −0.22 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (3)
Secondary atom site location: difference Fourier map
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).
xyzUiso*/Ueq
F10.24629 (11)−0.31171 (17)0.68919 (5)0.0261 (3)
O10.33585 (12)0.28450 (17)0.45542 (5)0.0178 (3)
O20.05794 (13)−0.32557 (18)0.41030 (5)0.0205 (3)
O30.13190 (13)0.13025 (19)0.23839 (5)0.0226 (3)
C10.26630 (17)0.2332 (3)0.38638 (8)0.0169 (3)
C20.17422 (16)0.0346 (3)0.36799 (7)0.0155 (3)
C30.14094 (16)−0.1427 (3)0.42424 (7)0.0147 (3)
C40.19425 (16)−0.2340 (3)0.56069 (7)0.0163 (3)
C50.26679 (17)−0.1674 (3)0.62980 (7)0.0185 (3)
C60.36078 (17)0.0417 (3)0.64257 (8)0.0191 (3)
C70.38313 (17)0.1905 (3)0.58328 (8)0.0182 (3)
C80.21614 (16)−0.0827 (3)0.50018 (7)0.0142 (3)
C90.30989 (16)0.1270 (3)0.51258 (7)0.0147 (3)
C100.10652 (17)−0.0034 (3)0.28948 (7)0.0187 (3)
H10.28300.34420.34780.0203*
H20.1311−0.37820.55410.0195*
H30.40870.08100.69140.0229*
H40.44720.33380.59040.0218*
H50.0388−0.14140.27830.0224*
U11U22U33U12U13U23
F10.0315 (5)0.0312 (5)0.0153 (5)−0.0033 (4)0.0012 (4)0.0069 (4)
O10.0222 (5)0.0154 (5)0.0157 (5)−0.0035 (4)0.0014 (4)0.0000 (4)
O20.0223 (5)0.0183 (5)0.0204 (5)−0.0056 (4)−0.0003 (4)−0.0014 (4)
O30.0293 (6)0.0222 (6)0.0161 (5)0.0045 (5)0.0013 (4)0.0016 (4)
C10.0186 (7)0.0171 (7)0.0153 (6)0.0018 (5)0.0033 (5)0.0010 (5)
C20.0146 (6)0.0166 (7)0.0154 (7)0.0024 (5)0.0026 (5)−0.0014 (5)
C30.0125 (6)0.0151 (6)0.0167 (7)0.0024 (5)0.0021 (5)−0.0014 (5)
C40.0149 (6)0.0163 (7)0.0178 (7)0.0001 (5)0.0029 (5)−0.0001 (6)
C50.0192 (7)0.0215 (7)0.0152 (7)0.0032 (6)0.0042 (5)0.0033 (6)
C60.0177 (6)0.0246 (8)0.0147 (6)0.0027 (6)−0.0003 (5)−0.0034 (6)
C70.0163 (7)0.0177 (7)0.0204 (7)0.0002 (5)0.0010 (5)−0.0051 (6)
C80.0120 (6)0.0154 (6)0.0154 (7)0.0019 (5)0.0023 (5)−0.0015 (5)
C90.0146 (6)0.0151 (7)0.0149 (6)0.0016 (5)0.0032 (5)0.0002 (5)
C100.0190 (7)0.0197 (7)0.0171 (7)0.0024 (6)0.0005 (5)−0.0015 (6)
F1—C51.3606 (17)C4—C81.4020 (19)
O1—C11.3427 (17)C5—C61.393 (2)
O1—C91.3835 (17)C6—C71.377 (2)
O2—C31.2282 (17)C7—C91.3946 (19)
O3—C101.2155 (17)C8—C91.394 (2)
C1—C21.352 (2)C1—H10.950
C2—C31.4579 (19)C4—H20.950
C2—C101.4796 (18)C6—H30.950
C3—C81.4780 (18)C7—H40.950
C4—C51.3723 (18)C10—H50.950
O1···C32.8691 (18)C4···H33.2823
O2···C13.576 (2)C5···H43.2513
O2···C42.8658 (17)C6···H23.2881
O2···C102.8760 (18)C8···H43.2937
O3···C12.8344 (19)C9···H13.1941
C1···C73.587 (3)C9···H23.2746
C1···C82.760 (2)C9···H33.2509
C2···C92.7704 (19)C10···H12.5600
C4···C72.813 (2)H1···H53.4953
C5···C92.721 (2)H3···H42.3436
C6···C82.796 (2)F1···H3i2.6307
F1···F1i3.5513 (16)F1···H4vi3.1761
F1···F1ii3.5513 (16)F1···H5iv3.4684
F1···O2iii3.5044 (15)F1···H5v2.6941
F1···O3iv3.4981 (16)O1···H2vii3.1318
F1···O3v3.5584 (16)O1···H4xiv2.8987
F1···C6i3.315 (2)O2···H1vi2.8570
F1···C7vi3.5947 (19)O2···H2iii2.3533
F1···C10iv3.3360 (18)O3···H1x2.3664
F1···C10v3.3800 (18)O3···H3xii2.4781
O1···O2vii3.1431 (15)O3···H4xii2.9229
O1···C3vii3.5781 (19)O3···H5xi2.9244
O1···C4vii3.5315 (19)C1···H2iv3.4844
O1···C6viii3.5869 (19)C1···H3viii3.4931
O1···C7viii3.5649 (19)C1···H4xiv3.3095
O2···F1iii3.5044 (15)C1···H5xi3.5228
O2···O1vi3.1431 (15)C2···H2iv3.4665
O2···C1vi3.0162 (19)C2···H3viii3.5928
O2···C4iii3.2351 (19)C3···H1vi3.4163
O2···C7iv3.5572 (19)C3···H2iii3.4741
O2···C9iv3.4951 (19)C3···H4viii3.4389
O3···F1iv3.4981 (16)C4···H4vi3.1477
O3···F1ix3.5584 (16)C5···H4vi3.2399
O3···O3x3.3650 (17)C5···H5iv3.4912
O3···O3xi3.3650 (17)C5···H5v3.4391
O3···C1x3.3077 (19)C6···H1viii3.5277
O3···C2xi3.4099 (18)C6···H5v3.5118
O3···C6xii3.1985 (18)C7···H2vii3.1377
O3···C7xii3.4120 (19)C8···H4viii3.5193
O3···C10xi2.9773 (19)C9···H2vii3.2243
C1···O2vii3.0162 (19)C10···H1x2.8205
C1···O3xi3.3077 (19)C10···H3xii3.2620
C1···C6viii3.390 (2)H1···O2vii2.8570
C2···O3x3.4099 (18)H1···O3xi2.3664
C2···C4iv3.453 (2)H1···C3vii3.4163
C2···C5iv3.546 (2)H1···C6viii3.5277
C3···O1vi3.5781 (19)H1···C10xi2.8205
C3···C4iv3.403 (2)H1···H3viii3.5122
C3···C8iv3.461 (2)H1···H4xiv2.9261
C4···O1vi3.5315 (19)H1···H5xi2.7690
C4···O2iii3.2351 (19)H2···O1vi3.1318
C4···C2iv3.453 (2)H2···O2iii2.3533
C4···C3iv3.403 (2)H2···C1iv3.4844
C4···C7vi3.557 (3)H2···C2iv3.4665
C5···C2iv3.546 (2)H2···C3iii3.4741
C5···C10iv3.517 (2)H2···C7vi3.1377
C6···F1ii3.315 (2)H2···C9vi3.2243
C6···O1viii3.5869 (19)H2···H2iii3.0288
C6···O3xiii3.1985 (18)H2···H4vi2.9843
C6···C1viii3.390 (2)H3···F1ii2.6307
C7···F1vii3.5947 (19)H3···O3xiii2.4781
C7···O1viii3.5649 (19)H3···C1viii3.4931
C7···O2iv3.5572 (19)H3···C2viii3.5928
C7···O3xiii3.4120 (19)H3···C10xiii3.2620
C7···C4vii3.557 (3)H3···H1viii3.5122
C7···C9viii3.562 (2)H3···H5v3.0440
C8···C3iv3.461 (2)H4···F1vii3.1761
C8···C8iv3.518 (2)H4···O1xiv2.8987
C9···O2iv3.4951 (19)H4···O3xiii2.9229
C9···C7viii3.562 (2)H4···C1xiv3.3095
C9···C9viii3.374 (2)H4···C3viii3.4389
C10···F1iv3.3360 (18)H4···C4vii3.1477
C10···F1ix3.3800 (18)H4···C5vii3.2399
C10···O3x2.9773 (19)H4···C8viii3.5193
C10···C5iv3.517 (2)H4···H1xiv2.9261
F1···H22.5447H4···H2vii2.9843
F1···H32.5415H5···F1iv3.4684
O1···H42.5219H5···F1ix2.6941
O2···H22.6151H5···O3x2.9244
O2···H52.5814H5···C1x3.5228
O3···H12.5100H5···C5iv3.4912
C1···H53.2808H5···C5ix3.4391
C3···H13.2935H5···C6ix3.5118
C3···H22.6889H5···H1x2.7690
C3···H52.6767H5···H3ix3.0440
C1—O1—C9118.43 (11)C4—C8—C9118.99 (12)
O1—C1—C2124.57 (13)O1—C9—C7116.03 (12)
C1—C2—C3121.05 (12)O1—C9—C8121.94 (11)
C1—C2—C10119.43 (13)C7—C9—C8122.02 (13)
C3—C2—C10119.53 (12)O3—C10—C2124.30 (13)
O2—C3—C2123.45 (12)O1—C1—H1117.713
O2—C3—C8122.66 (12)C2—C1—H1117.717
C2—C3—C8113.89 (12)C5—C4—H2121.008
C5—C4—C8117.98 (13)C8—C4—H2121.007
F1—C5—C4118.76 (13)C5—C6—H3120.543
F1—C5—C6117.91 (12)C7—C6—H3120.538
C4—C5—C6123.32 (13)C6—C7—H4120.618
C5—C6—C7118.92 (13)C9—C7—H4120.626
C6—C7—C9118.76 (13)O3—C10—H5117.845
C3—C8—C4120.90 (12)C2—C10—H5117.850
C3—C8—C9120.11 (12)
C1—O1—C9—C7−179.22 (10)C8—C4—C5—F1179.77 (11)
C1—O1—C9—C80.80 (17)C8—C4—C5—C6−0.1 (2)
C9—O1—C1—C2−1.26 (19)H2—C4—C5—F1−0.2
C9—O1—C1—H1178.7H2—C4—C5—C6179.9
O1—C1—C2—C30.9 (2)H2—C4—C8—C30.3
O1—C1—C2—C10−179.01 (11)H2—C4—C8—C9−179.9
H1—C1—C2—C3−179.1F1—C5—C6—C7−179.98 (11)
H1—C1—C2—C101.0F1—C5—C6—H30.0
C1—C2—C3—O2179.92 (12)C4—C5—C6—C7−0.1 (2)
C1—C2—C3—C80.01 (18)C4—C5—C6—H3179.9
C1—C2—C10—O32.2 (2)C5—C6—C7—C90.4 (2)
C1—C2—C10—H5−177.8C5—C6—C7—H4−179.6
C3—C2—C10—O3−177.66 (12)H3—C6—C7—C9−179.6
C3—C2—C10—H52.3H3—C6—C7—H40.4
C10—C2—C3—O2−0.21 (19)C6—C7—C9—O1179.57 (11)
C10—C2—C3—C8179.87 (11)C6—C7—C9—C8−0.5 (2)
O2—C3—C8—C4−0.5 (2)H4—C7—C9—O1−0.4
O2—C3—C8—C9179.68 (12)H4—C7—C9—C8179.6
C2—C3—C8—C4179.39 (11)C3—C8—C9—O10.01 (19)
C2—C3—C8—C9−0.40 (17)C3—C8—C9—C7−179.97 (11)
C5—C4—C8—C3−179.74 (11)C4—C8—C9—O1−179.78 (11)
C5—C4—C8—C90.05 (19)C4—C8—C9—C70.24 (19)
D—H···AD—HH···AD···AD—H···A
C1—H1···O3xi0.952.373.308 (2)171
C4—H2···O2iii0.952.353.235 (2)154
C6—H3···O3xiii0.952.483.198 (2)133
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1—H1⋯O3i 0.952.373.308 (2)171
C4—H2⋯O2ii 0.952.353.235 (2)154
C6—H3⋯O3iii 0.952.483.198 (2)133

Symmetry codes: (i) ; (ii) ; (iii) .

  7 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Principles and applications of halogen bonding in medicinal chemistry and chemical biology.

Authors:  Rainer Wilcken; Markus O Zimmermann; Andreas Lange; Andreas C Joerger; Frank M Boeckler
Journal:  J Med Chem       Date:  2013-01-03       Impact factor: 7.446

3.  Halogen bonding based recognition processes: a world parallel to hydrogen bonding.

Authors:  Pierangelo Metrangolo; Hannes Neukirch; Tullio Pilati; Giuseppe Resnati
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4.  Halogen bonds in biological molecules.

Authors:  Pascal Auffinger; Franklin A Hays; Eric Westhof; P Shing Ho
Journal:  Proc Natl Acad Sci U S A       Date:  2004-11-19       Impact factor: 11.205

5.  Halogen interactions in protein-ligand complexes: implications of halogen bonding for rational drug design.

Authors:  Suman Sirimulla; Jake B Bailey; Rahulsimham Vegesna; Mahesh Narayan
Journal:  J Chem Inf Model       Date:  2013-11-13       Impact factor: 4.956

6.  6-Chloro-4-oxo-4H-chromene-3-carb-aldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-05

7.  6-Bromo-4-oxo-4H-chromene-3-carb-alde-hyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-16
  7 in total
  1 in total

1.  6-Iodo-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-06-04
  1 in total

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