Literature DB >> 25161562

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

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H5FO3, the non-H atoms of the 8-fluoro-chromone unit are essentially coplanar (r.m.s. deviation = 0.0259 Å), with a largest deviation from the mean plane of 0.0660 (12) Å for the chromone carbonyl O atom. The formyl group is twisted with respect to the attached ring [C-C-C-O torsion angles = -11.00 (19) and 170.81 (11)°]. In the crystal, mol-ecules are linked via weak C-H⋯O hydrogen bonds along the a axis and [-101], forming corrugated layers parallel to (010). In addition, π-π stacking inter-actions [centroid-centroid distance between the planes of the pyran and benzene rings = 3.519 (2) Å] are observed between these layers.

Entities:  

Year:  2014        PMID： 25161562      PMCID： PMC4120633          DOI： 10.1107/S1600536814013208

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


Related literature

For related structures, see: Ishikawa & Motohashi (2013 ▶); Ishikawa (2014 ▶). For the synthesis of the precursor of the title compound, see: Valoti et al. (2001 ▶). 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 = 6.6643 (12) Å b = 8.395 (5) Å c = 14.247 (4) Å β = 97.865 (16)° V = 789.6 (6) Å3 Z = 4 Mo Kα radiation μ = 0.14 mm−1 T = 100 K 0.40 × 0.40 × 0.20 mm

Data collection

Rigaku AFC-7R diffractometer 2445 measured reflections 1810 independent reflections 1606 reflections with F 2 > 2σ(F 2) R int = 0.049 3 standard reflections every 150 reflections intensity decay: −0.4%

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.109 S = 1.07 1810 reflections 127 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.36 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/S1600536814013208/lh5713sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013208/lh5713Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814013208/lh5713Isup3.cml CCDC reference: 1007014 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H5FO3F(000) = 392.00
Mr = 192.15Dx = 1.616 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 6.6643 (12) Åθ = 15.5–17.4°
b = 8.395 (5) ŵ = 0.14 mm−1
c = 14.247 (4) ÅT = 100 K
β = 97.865 (16)°Block, yellow
V = 789.6 (6) Å30.40 × 0.40 × 0.20 mm
Z = 4
Rigaku AFC-7R diffractometerθmax = 27.5°
ω–2θ scansh = −8→8
2445 measured reflectionsk = −6→10
1810 independent reflectionsl = −10→18
1606 reflections with F2 > 2σ(F2)3 standard reflections every 150 reflections
Rint = 0.049 intensity decay: −0.4%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0617P)2 + 0.3187P] where P = (Fo2 + 2Fc2)/3
1810 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Primary atom site location: structure-invariant direct methods
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
F10.63662 (11)0.31393 (11)−0.11055 (6)0.0262 (3)
O10.70736 (13)0.13166 (11)0.04296 (6)0.0175 (3)
O21.28166 (13)0.05710 (12)0.17921 (6)0.0211 (3)
O30.80302 (16)−0.13767 (12)0.29126 (7)0.0265 (3)
C10.74226 (18)0.04263 (15)0.12185 (8)0.0174 (3)
C20.92737 (18)0.01472 (14)0.17064 (8)0.0156 (3)
C31.10896 (18)0.08367 (14)0.14003 (8)0.0148 (3)
C41.22460 (18)0.26974 (15)0.01980 (9)0.0169 (3)
C51.18179 (19)0.36449 (15)−0.05972 (9)0.0190 (3)
C60.9826 (2)0.38000 (15)−0.10529 (9)0.0193 (3)
C70.83046 (19)0.30073 (15)−0.06889 (9)0.0180 (3)
C81.06800 (17)0.18914 (14)0.05669 (8)0.0146 (3)
C90.86964 (18)0.20612 (14)0.01198 (8)0.0152 (3)
C100.9457 (2)−0.09092 (15)0.25433 (9)0.0197 (3)
H10.6287−0.00400.14500.0209*
H21.36040.25910.04960.0203*
H31.28840.4197−0.08370.0228*
H40.95340.4442−0.16040.0231*
H51.0775−0.12430.28090.0236*
U11U22U33U12U13U23
F10.0193 (4)0.0333 (5)0.0246 (5)0.0075 (4)−0.0019 (3)0.0064 (4)
O10.0142 (4)0.0207 (5)0.0178 (5)0.0016 (4)0.0028 (4)0.0012 (4)
O20.0171 (5)0.0282 (5)0.0173 (5)0.0014 (4)−0.0006 (4)0.0027 (4)
O30.0355 (6)0.0226 (5)0.0239 (5)−0.0023 (4)0.0130 (4)0.0020 (4)
C10.0197 (6)0.0163 (6)0.0175 (6)0.0008 (5)0.0071 (5)−0.0010 (5)
C20.0198 (6)0.0138 (6)0.0140 (6)0.0014 (5)0.0048 (5)−0.0016 (5)
C30.0179 (6)0.0146 (6)0.0121 (5)0.0018 (5)0.0025 (4)−0.0028 (4)
C40.0164 (6)0.0171 (6)0.0175 (6)0.0005 (5)0.0033 (5)−0.0017 (5)
C50.0224 (6)0.0169 (6)0.0192 (6)−0.0001 (5)0.0077 (5)0.0000 (5)
C60.0277 (7)0.0164 (6)0.0144 (6)0.0051 (5)0.0048 (5)0.0006 (5)
C70.0187 (6)0.0189 (6)0.0158 (6)0.0062 (5)−0.0003 (5)−0.0016 (5)
C80.0176 (6)0.0133 (6)0.0130 (5)0.0017 (5)0.0029 (5)−0.0020 (5)
C90.0167 (6)0.0140 (6)0.0157 (6)0.0020 (5)0.0045 (5)−0.0020 (5)
C100.0275 (7)0.0166 (6)0.0156 (6)0.0006 (5)0.0050 (5)−0.0014 (5)
F1—C71.3504 (15)C4—C81.4048 (18)
O1—C11.3433 (15)C5—C61.4017 (18)
O1—C91.3733 (16)C6—C71.372 (2)
O2—C31.2289 (15)C7—C91.3943 (18)
O3—C101.2133 (18)C8—C91.3940 (16)
C1—C21.3510 (17)C1—H10.950
C2—C31.4609 (18)C4—H20.950
C2—C101.4776 (18)C5—H30.950
C3—C81.4764 (17)C6—H40.950
C4—C51.3817 (18)C10—H50.950
F1···O12.6580 (14)C8···H33.2724
O1···C32.8679 (15)C9···H13.1799
O2···C13.5778 (16)C9···H23.2714
O2···C42.8728 (18)C9···H43.2729
O2···C102.8910 (18)C10···H12.5538
O3···C12.8307 (17)H1···H53.4830
C1···C73.586 (2)H2···H32.3255
C1···C82.7638 (18)H3···H42.3559
C2···C92.7571 (18)F1···H1xiii3.1465
C4···C72.7668 (18)F1···H2iii3.1555
C5···C92.7785 (19)F1···H3iii2.5618
C6···C82.8031 (19)F1···H3x3.5405
F1···O2i3.332 (3)F1···H5ii3.0285
F1···O2ii3.4454 (15)O1···H1xiii3.4194
F1···C2ii3.5415 (16)O1···H2iii2.5611
F1···C4iii3.5386 (17)O1···H2i3.5413
F1···C5iii3.2393 (17)O2···H1vi2.4819
F1···C10ii3.1720 (19)O2···H4v2.4119
O1···O2i3.5495 (16)O2···H5vii2.8654
O1···O3iv3.0624 (16)O3···H1viii3.2215
O1···C3i3.5265 (18)O3···H2xii3.0871
O1···C4iii3.3931 (16)O3···H3ix2.5650
O1···C4i3.532 (3)O3···H4ix2.9967
O1···C8i3.477 (2)C1···H2iii3.1811
O2···F1i3.332 (3)C1···H2i3.5205
O2···F1v3.4454 (15)C3···H1vi3.5325
O2···O1i3.5495 (16)C3···H4v3.4094
O2···C1vi3.2850 (17)C3···H5vii3.3166
O2···C6v3.2207 (17)C4···H1i3.4743
O2···C7i3.425 (3)C4···H4x3.4405
O2···C9i3.5451 (18)C4···H5vii3.0932
O2···C10vii3.530 (3)C5···H1i3.5564
O3···O1viii3.0624 (16)C6···H5i3.2790
O3···C1viii2.988 (3)C6···H5ii3.5954
O3···C2viii3.376 (3)C7···H3x3.3670
O3···C5ix3.300 (2)C7···H5i3.4926
O3···C6ix3.503 (2)C8···H4x3.4258
O3···C9viii3.4329 (18)C8···H5vii3.4483
C1···O2iii3.2850 (17)C9···H2iii3.5355
C1···O3iv2.988 (3)C9···H3x3.5098
C1···C4i3.335 (3)C10···H2xii3.1732
C1···C5i3.584 (3)C10···H3ix3.0252
C1···C8i3.569 (2)C10···H4i3.3595
C2···F1v3.5415 (16)H1···F1xiii3.1465
C2···O3iv3.376 (3)H1···O1xiii3.4194
C2···C5i3.584 (3)H1···O2iii2.4819
C2···C6i3.516 (3)H1···O3iv3.2215
C2···C7i3.516 (3)H1···C3iii3.5325
C3···O1i3.5265 (18)H1···C4i3.4743
C3···C7i3.423 (3)H1···C5i3.5564
C3···C9i3.273 (2)H1···H2iii3.0424
C4···F1vi3.5386 (17)H1···H2i3.5115
C4···O1vi3.3931 (16)H1···H4ix3.1928
C4···O1i3.532 (3)H2···F1vi3.1555
C4···C1i3.335 (3)H2···O1vi2.5611
C4···C6x3.535 (3)H2···O1i3.5413
C5···F1vi3.2393 (17)H2···O3vii3.0871
C5···O3xi3.300 (2)H2···C1vi3.1811
C5···C1i3.584 (3)H2···C1i3.5205
C5···C2i3.584 (3)H2···C9vi3.5355
C5···C6x3.469 (2)H2···C10vii3.1732
C5···C7x3.362 (3)H2···H1vi3.0424
C6···O2ii3.2207 (17)H2···H1i3.5115
C6···O3xi3.503 (2)H2···H3xiv3.5607
C6···C2i3.516 (3)H2···H5vii2.5859
C6···C4x3.535 (3)H3···F1vi2.5618
C6···C5x3.469 (2)H3···F1x3.5405
C6···C6x3.595 (2)H3···O3xi2.5650
C6···C10i3.302 (3)H3···C7x3.3670
C7···O2i3.425 (3)H3···C9x3.5098
C7···C2i3.516 (3)H3···C10xi3.0252
C7···C3i3.423 (3)H3···H2xiv3.5607
C7···C5x3.362 (3)H3···H5xi3.3769
C8···O1i3.477 (2)H4···O2ii2.4119
C8···C1i3.569 (2)H4···O3xi2.9967
C8···C9i3.500 (3)H4···C3ii3.4094
C9···O2i3.5451 (18)H4···C4x3.4405
C9···O3iv3.4329 (18)H4···C8x3.4258
C9···C3i3.273 (2)H4···C10i3.3595
C9···C8i3.500 (3)H4···H1xi3.1928
C10···F1v3.1720 (19)H4···H5i3.1787
C10···O2xii3.530 (3)H4···H5ii2.9478
C10···C6i3.302 (3)H5···F1v3.0285
F1···H42.5628H5···O2xii2.8654
O2···H22.6123H5···C3xii3.3166
O2···H52.6094H5···C4xii3.0932
O3···H12.5079H5···C6i3.2790
C1···H53.2720H5···C6v3.5954
C3···H13.2941H5···C7i3.4926
C3···H22.6881H5···C8xii3.4483
C3···H52.6900H5···H2xii2.5859
C4···H43.2758H5···H3ix3.3769
C6···H23.2742H5···H4i3.1787
C7···H33.2451H5···H4v2.9478
C1—O1—C9117.93 (10)C4—C8—C9119.10 (11)
O1—C1—C2124.64 (12)O1—C9—C7117.27 (11)
C1—C2—C3120.87 (11)O1—C9—C8123.09 (11)
C1—C2—C10119.22 (12)C7—C9—C8119.64 (12)
C3—C2—C10119.88 (11)O3—C10—C2124.11 (12)
O2—C3—C2123.72 (11)O1—C1—H1117.679
O2—C3—C8122.19 (12)C2—C1—H1117.685
C2—C3—C8114.09 (10)C5—C4—H2119.881
C5—C4—C8120.23 (11)C8—C4—H2119.890
C4—C5—C6120.63 (12)C4—C5—H3119.685
C5—C6—C7118.80 (12)C6—C5—H3119.687
F1—C7—C6120.39 (12)C5—C6—H4120.605
F1—C7—C9118.01 (12)C7—C6—H4120.598
C6—C7—C9121.60 (12)O3—C10—H5117.944
C3—C8—C4121.65 (11)C2—C10—H5117.943
C3—C8—C9119.23 (11)
C1—O1—C9—C7−178.72 (10)C8—C4—C5—C6−0.79 (19)
C1—O1—C9—C82.18 (16)C8—C4—C5—H3179.2
C9—O1—C1—C2−3.31 (17)H2—C4—C5—C6179.2
C9—O1—C1—H1176.7H2—C4—C5—H3−0.8
O1—C1—C2—C30.63 (19)H2—C4—C8—C3−1.6
O1—C1—C2—C10−177.55 (10)H2—C4—C8—C9−180.0
H1—C1—C2—C3−179.4C4—C5—C6—C70.70 (19)
H1—C1—C2—C102.5C4—C5—C6—H4−179.3
C1—C2—C3—O2−176.84 (11)H3—C5—C6—C7−179.3
C1—C2—C3—C82.95 (16)H3—C5—C6—H40.7
C1—C2—C10—O3−11.00 (19)C5—C6—C7—F1179.50 (11)
C1—C2—C10—H5169.0C5—C6—C7—C90.15 (19)
C3—C2—C10—O3170.81 (11)H4—C6—C7—F1−0.5
C3—C2—C10—H5−9.2H4—C6—C7—C9−179.9
C10—C2—C3—O21.32 (18)F1—C7—C9—O10.61 (17)
C10—C2—C3—C8−178.89 (10)F1—C7—C9—C8179.74 (10)
O2—C3—C8—C4−2.43 (18)C6—C7—C9—O1179.97 (11)
O2—C3—C8—C9175.92 (10)C6—C7—C9—C8−0.90 (18)
C2—C3—C8—C4177.77 (10)C3—C8—C9—O11.48 (17)
C2—C3—C8—C9−3.87 (15)C3—C8—C9—C7−177.60 (10)
C5—C4—C8—C3178.39 (11)C4—C8—C9—O1179.88 (10)
C5—C4—C8—C90.03 (18)C4—C8—C9—C70.80 (17)
D—H···AD—HH···AD···AD—H···A
C1vi—H1vi···O20.952.483.285 (2)142 (1)
C6v—H4v···O20.952.413.221 (2)143 (1)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1i—H1i⋯O20.952.483.285 (2)142 (1)
C6ii—H4ii⋯O20.952.413.221 (2)143 (1)

Symmetry codes: (i) ; (ii) .

  8 in total

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