Literature DB >> 25161600

6-Chloro-7-fluoro-4-oxo-4H-chromene-3-carbaldehyde.

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H4ClFO3, a chlorinated and fluorinated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. = 0.0336 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.062 (2) Å] being for a benzene-ring C atom. In the crystal, mol-ecules are linked through stacking inter-actions [centroid-centroid distance between the benzene and pyran rings = 3.958 (3) Å and inter-planar distance = 3.259 (3) Å], C-H⋯O hydrogen bonds, and short C⋯O contacts [2.879 (3) Å]. Unsymmetrical halogen-halogen inter-actions between the Cl and F atoms [Cl⋯F = 3.049 (3) Å, C-Cl⋯F = 148.10 (9)° and C-F⋯Cl = 162.06 (13)°] are also formed, giving a meandering two-dimensional network along the a axis.

Entities:  

Keywords:  crystal structure

Year:  2014        PMID： 25161600      PMCID： PMC4120572          DOI： 10.1107/S1600536814014706

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 halogen bonding, see: Auffinger et al. (2004 ▶); Metrangolo et al. (2005 ▶); Wilcken et al. (2013 ▶); Sirimulla et al. (2013 ▶). For halogen–halogen inter­actions, see: Hathwar & Guru Row (2011 ▶); Metrangolo & Resnati (2014 ▶); Mukherjee & Desiraju (2014 ▶).

Experimental

Crystal data

C10H4ClFO3 M = 226.59 Orthorhombic, a = 5.725 (3) Å b = 32.57 (3) Å c = 4.706 (4) Å V = 877.4 (11) Å3 Z = 4 Mo Kα radiation μ = 0.43 mm−1 T = 100 K 0.40 × 0.25 × 0.08 mm

Data collection

Rigaku AFC-7R diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.894, T max = 0.966 1692 measured reflections 1346 independent reflections 1249 reflections with F 2 > 2σ(F 2) R int = 0.009 3 standard reflections every 150 reflections intensity decay: −0.1%

Refinement

R[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 0.074 S = 1.09 1346 reflections 136 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.25 e Å−3 Absolute structure: Flack (1983 ▶), 105 Friedel Pairs Absolute structure parameter: 0.31 (9) 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/S1600536814014706/zl2593sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014706/zl2593Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814014706/zl2593Isup3.cml CCDC reference: 1009489 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H4ClFO3F(000) = 456.00
Mr = 226.59Dx = 1.715 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 5.725 (3) Åθ = 15.0–17.5°
b = 32.57 (3) ŵ = 0.43 mm−1
c = 4.706 (4) ÅT = 100 K
V = 877.4 (11) Å3Prismatic, yellow
Z = 40.40 × 0.25 × 0.08 mm
Rigaku AFC-7R diffractometerRint = 0.009
ω scansθmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)h = −4→7
Tmin = 0.894, Tmax = 0.966k = 0→42
1692 measured reflectionsl = −3→6
1346 independent reflections3 standard reflections every 150 reflections
1249 reflections with F2 > 2σ(F2) intensity decay: −0.1%
Refinement on F2Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.074w = 1/[σ2(Fo2) + (0.0395P)2 + 0.3855P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1346 reflectionsΔρmax = 0.29 e Å−3
136 parametersΔρmin = −0.25 e Å−3
0 restraintsAbsolute structure: Flack (1983), 105 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.31 (9)
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
Cl10.39186 (10)0.273972 (16)1.18743 (14)0.02563 (15)
F1−0.0630 (3)0.29836 (4)1.4050 (3)0.0262 (4)
O1−0.1743 (3)0.41526 (4)0.8442 (4)0.0170 (4)
O20.4433 (3)0.39789 (5)0.4232 (4)0.0197 (4)
O30.0422 (3)0.49703 (5)0.2146 (4)0.0221 (4)
C1−0.1015 (4)0.44135 (6)0.6415 (5)0.0164 (5)
C20.1017 (4)0.43740 (6)0.4982 (5)0.0150 (4)
C30.2589 (4)0.40294 (6)0.5529 (5)0.0151 (5)
C40.3078 (4)0.34031 (6)0.8557 (5)0.0166 (5)
C50.2284 (4)0.31479 (6)1.0679 (5)0.0179 (5)
C60.0125 (4)0.32307 (6)1.1954 (5)0.0179 (5)
C7−0.1221 (4)0.35619 (6)1.1204 (5)0.0168 (5)
C80.1766 (4)0.37479 (6)0.7742 (5)0.0146 (5)
C9−0.0373 (4)0.38186 (6)0.9084 (5)0.0139 (5)
C100.1639 (4)0.46812 (6)0.2808 (5)0.0174 (5)
H1−0.19910.46400.59600.0197*
H20.45200.33460.76400.0200*
H3−0.26780.36141.21000.0202*
H40.30940.46500.18610.0208*
U11U22U33U12U13U23
Cl10.0256 (3)0.0191 (3)0.0322 (3)0.0053 (3)−0.0045 (3)0.0062 (3)
F10.0290 (8)0.0242 (7)0.0256 (8)−0.0050 (7)−0.0003 (7)0.0083 (6)
O10.0134 (7)0.0183 (7)0.0194 (8)0.0035 (6)0.0028 (7)0.0013 (7)
O20.0160 (8)0.0231 (8)0.0199 (8)0.0032 (7)0.0050 (8)0.0007 (7)
O30.0219 (8)0.0194 (7)0.0250 (9)0.0017 (7)−0.0026 (8)0.0047 (7)
C10.0170 (10)0.0144 (9)0.0180 (11)0.0007 (8)−0.0019 (11)−0.0003 (9)
C20.0160 (10)0.0143 (9)0.0146 (10)0.0003 (9)−0.0007 (10)−0.0016 (8)
C30.0150 (10)0.0159 (10)0.0144 (10)−0.0004 (9)−0.0025 (10)−0.0029 (9)
C40.0161 (10)0.0170 (10)0.0169 (11)0.0015 (9)−0.0019 (10)−0.0031 (9)
C50.0193 (11)0.0136 (10)0.0207 (11)0.0023 (9)−0.0049 (10)−0.0004 (9)
C60.0208 (11)0.0168 (10)0.0162 (11)−0.0050 (9)−0.0007 (11)0.0007 (10)
C70.0152 (10)0.0202 (10)0.0150 (10)−0.0022 (9)0.0002 (10)−0.0025 (9)
C80.0157 (10)0.0142 (9)0.0137 (10)−0.0001 (8)−0.0013 (9)−0.0026 (9)
C90.0137 (10)0.0134 (9)0.0147 (10)−0.0004 (8)−0.0034 (9)−0.0029 (9)
C100.0175 (10)0.0191 (10)0.0156 (10)−0.0009 (9)−0.0010 (10)−0.0013 (9)
Cl1—C51.720 (3)C4—C51.377 (4)
F1—C61.344 (3)C4—C81.405 (3)
O1—C11.344 (3)C5—C61.400 (4)
O1—C91.375 (3)C6—C71.372 (3)
O2—C31.231 (3)C7—C91.389 (3)
O3—C101.212 (3)C8—C91.397 (3)
C1—C21.351 (4)C1—H10.950
C2—C31.461 (3)C4—H20.950
C2—C101.474 (3)C7—H30.950
C3—C81.465 (3)C10—H40.950
Cl1···F12.908 (2)F1···H32.5356
F1···C93.589 (4)O1···H32.5157
O1···C32.862 (3)O2···H22.6126
O1···C63.590 (4)O2···H42.5720
O2···C13.576 (4)O3···H12.5075
O2···C42.874 (3)C1···H43.2741
O2···C102.870 (3)C3···H13.2973
O3···C12.828 (3)C3···H22.6768
C1···C73.576 (4)C3···H42.6745
C1···C82.761 (4)C5···H33.2890
C2···C92.763 (4)C6···H23.2547
C4···C72.806 (4)C8···H33.2967
C5···C92.766 (4)C9···H13.1900
C6···C82.766 (4)C9···H23.2681
Cl1···F1i3.380 (3)C10···H12.5568
Cl1···F1ii3.049 (3)H1···H43.4924
F1···Cl1iii3.380 (3)Cl1···H2v3.3732
F1···Cl1iv3.049 (3)Cl1···H3i3.4511
F1···C4v3.297 (3)F1···H2vi3.4577
F1···C5v3.577 (4)F1···H2v3.5970
F1···C8v3.331 (3)O1···H2iii3.4090
O1···O2iii3.006 (3)O1···H3viii3.5035
O1···O2vi3.540 (3)O1···H4v3.5895
O1···O3v3.416 (3)O2···H1i3.0802
O1···C2v3.533 (4)O2···H3vii2.2707
O1···C3iii3.545 (3)O3···H1viii3.3969
O1···C10v3.307 (3)O3···H1xi2.4042
O2···O1vii3.540 (3)O3···H4ix2.9039
O2···O1i3.006 (3)O3···H4x2.6777
O2···C1i3.138 (3)C1···H3viii3.4372
O2···C4viii3.354 (4)C1···H4v3.5633
O2···C5viii3.411 (4)C1···H4x3.4837
O2···C7vii3.173 (3)C2···H3viii3.5279
O2···C8viii3.496 (4)C2···H4v3.5642
O3···O1viii3.416 (3)C2···H4x3.3373
O3···O3ix3.352 (3)C3···H3vii3.4320
O3···O3x3.352 (3)C4···H3i3.0253
O3···C1viii3.353 (4)C5···H2v3.5757
O3···C1xi3.242 (3)C5···H3i3.3268
O3···C2ix3.123 (3)C7···H2iii3.0416
O3···C3ix3.534 (4)C9···H2iii3.3732
O3···C10ix2.879 (3)C10···H1xi3.5669
O3···C10x3.349 (4)C10···H4ix3.5488
C1···O2iii3.138 (3)C10···H4x2.8982
C1···O3v3.353 (4)H1···O2iii3.0802
C1···O3xii3.242 (3)H1···O3v3.3969
C1···C10v3.481 (4)H1···O3xii2.4042
C2···O1viii3.533 (4)H1···C10xii3.5669
C2···O3x3.123 (3)H1···H1xi3.3725
C2···C7viii3.435 (4)H1···H1xii3.3725
C2···C9viii3.407 (4)H1···H4iii3.4116
C3···O1i3.545 (3)H1···H4x3.2403
C3···O3x3.534 (4)H2···Cl1viii3.3732
C3···C6viii3.404 (4)H2···F1viii3.5970
C3···C7viii3.349 (4)H2···F1vii3.4577
C3···C9viii3.542 (4)H2···O1i3.4090
C4···F1viii3.297 (3)H2···C5viii3.5757
C4···O2v3.354 (4)H2···C7i3.0416
C4···C6viii3.581 (4)H2···C9i3.3732
C4···C7i3.531 (4)H2···H3vii3.1828
C5···F1viii3.577 (4)H2···H3i2.7815
C5···O2v3.411 (4)H3···Cl1iii3.4511
C6···C3v3.404 (4)H3···O1v3.5035
C6···C4v3.581 (4)H3···O2vi2.2707
C6···C8v3.337 (4)H3···C1v3.4372
C7···O2vi3.173 (3)H3···C2v3.5279
C7···C2v3.435 (4)H3···C3vi3.4320
C7···C3v3.349 (4)H3···C4iii3.0253
C7···C4iii3.531 (4)H3···C5iii3.3268
C7···C8v3.571 (4)H3···H2iii2.7815
C8···F1viii3.331 (3)H3···H2vi3.1828
C8···O2v3.496 (4)H4···O1viii3.5895
C8···C6viii3.337 (4)H4···O3ix2.6777
C8···C7viii3.571 (4)H4···O3x2.9039
C9···C2v3.407 (4)H4···C1viii3.5633
C9···C3v3.542 (4)H4···C1ix3.4837
C9···C10v3.506 (4)H4···C2viii3.5642
C10···O1viii3.307 (3)H4···C2ix3.3373
C10···O3ix3.349 (4)H4···C10ix2.8982
C10···O3x2.879 (3)H4···C10x3.5488
C10···C1viii3.481 (4)H4···H1i3.4116
C10···C9viii3.506 (4)H4···H1ix3.2403
C10···C10ix3.289 (4)H4···H4ix3.3442
C10···C10x3.289 (4)H4···H4x3.3442
Cl1···H22.8259
C1—O1—C9118.64 (17)C3—C8—C4121.5 (2)
O1—C1—C2124.15 (19)C3—C8—C9120.02 (19)
C1—C2—C3121.03 (19)C4—C8—C9118.5 (2)
C1—C2—C10119.31 (19)O1—C9—C7115.77 (19)
C3—C2—C10119.7 (2)O1—C9—C8122.08 (19)
O2—C3—C2122.9 (2)C7—C9—C8122.1 (2)
O2—C3—C8123.02 (19)O3—C10—C2124.5 (2)
C2—C3—C8114.06 (19)O1—C1—H1117.920
C5—C4—C8120.3 (2)C2—C1—H1117.932
Cl1—C5—C4121.60 (18)C5—C4—H2119.879
Cl1—C5—C6119.27 (17)C8—C4—H2119.849
C4—C5—C6119.1 (2)C6—C7—H3121.234
F1—C6—C5118.87 (19)C9—C7—H3121.245
F1—C6—C7118.6 (2)O3—C10—H4117.735
C5—C6—C7122.5 (2)C2—C10—H4117.738
C6—C7—C9117.5 (2)
C1—O1—C9—C7179.81 (16)C8—C4—C5—Cl1−176.25 (17)
C1—O1—C9—C81.4 (3)C8—C4—C5—C61.7 (3)
C9—O1—C1—C2−1.3 (3)H2—C4—C5—Cl13.7
C9—O1—C1—H1178.7H2—C4—C5—C6−178.3
O1—C1—C2—C31.1 (4)H2—C4—C8—C3−1.2
O1—C1—C2—C10−179.67 (17)H2—C4—C8—C9178.6
H1—C1—C2—C3−178.9Cl1—C5—C6—F1−1.2 (3)
H1—C1—C2—C100.3Cl1—C5—C6—C7176.87 (14)
C1—C2—C3—O2178.64 (19)C4—C5—C6—F1−179.17 (19)
C1—C2—C3—C8−0.9 (3)C4—C5—C6—C7−1.1 (4)
C1—C2—C10—O3−1.5 (4)F1—C6—C7—C9178.33 (16)
C1—C2—C10—H4178.5F1—C6—C7—H3−1.7
C3—C2—C10—O3177.79 (19)C5—C6—C7—C90.3 (4)
C3—C2—C10—H4−2.2C5—C6—C7—H3−179.7
C10—C2—C3—O2−0.6 (3)C6—C7—C9—O1−178.42 (18)
C10—C2—C3—C8179.86 (17)C6—C7—C9—C8−0.0 (3)
O2—C3—C8—C41.2 (4)H3—C7—C9—O11.6
O2—C3—C8—C9−178.51 (18)H3—C7—C9—C8180.0
C2—C3—C8—C4−179.22 (17)C3—C8—C9—O1−1.3 (3)
C2—C3—C8—C91.0 (3)C3—C8—C9—C7−179.63 (17)
C5—C4—C8—C3178.79 (18)C4—C8—C9—O1178.90 (18)
C5—C4—C8—C9−1.5 (3)C4—C8—C9—C70.6 (3)
D—H···AD—HH···AD···AD—H···A
C7—H3···O2vi0.952.273.173 (3)158
C1—H1···O3xii0.952.403.242 (3)147
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C7—H3⋯O2i 0.952.273.173 (3)158
C1—H1⋯O3ii 0.952.403.242 (3)147

Symmetry codes: (i) ; (ii) .

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