Literature DB >> 24860329

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

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H5ClO3, a chlorinated 3-formyl-chromone derivative, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.0456 Å) with the largest deviation from the least-squares plane [0.1136 (16) Å] being found for the ring-bound carbonyl O atom. In the crystal, mol-ecules are linked through stacking inter-actions along the b axis [shortest centroid-centroid distance between the pyran and benzene rings = 3.4959 (15) Å].

Entities:  

Year:  2014        PMID： 24860329      PMCID： PMC4011265          DOI： 10.1107/S1600536814007119

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 van der Waals radii; see: Bondi (1964 ▶). For halogen bonding, see: Auffinger et al. (2004 ▶); Metrangolo et al. (2005 ▶); Sirimulla et al. (2013 ▶).

Experimental

Crystal data

C10H5ClO3 M = 208.60 Triclinic, a = 6.5838 (16) Å b = 6.9579 (17) Å c = 10.265 (3) Å α = 71.22 (3)° β = 85.64 (2)° γ = 69.29 (3)° V = 416.0 (2) Å3 Z = 2 Mo Kα radiation μ = 0.43 mm−1 T = 100 K 0.36 × 0.25 × 0.12 mm

Data collection

Rigaku AFC-7R diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.891, T max = 0.950 2356 measured reflections 1906 independent reflections 1741 reflections with F 2 > 2σ(F 2) R int = 0.058 3 standard reflections every 150 reflections intensity decay: −0.9%

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.109 S = 1.10 1906 reflections 127 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.64 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: SIR88 (Burla et al., 1989 ▶); 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/S1600536814007119/tk5303sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007119/tk5303Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814007119/tk5303Isup3.cml CCDC reference: 994454 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H5ClO3Z = 2
Mr = 208.60F(000) = 212.00
Triclinic, P1Dx = 1.665 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 6.5838 (16) ÅCell parameters from 25 reflections
b = 6.9579 (17) Åθ = 15.3–17.2°
c = 10.265 (3) ŵ = 0.43 mm−1
α = 71.22 (3)°T = 100 K
β = 85.64 (2)°Plate, colourless
γ = 69.29 (3)°0.36 × 0.25 × 0.12 mm
V = 416.0 (2) Å3
Rigaku AFC-7R diffractometerRint = 0.058
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)h = −4→8
Tmin = 0.891, Tmax = 0.950k = −8→9
2356 measured reflectionsl = −13→13
1906 independent reflections3 standard reflections every 150 reflections
1741 reflections with F2 > 2σ(F2) intensity decay: −0.9%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0651P)2 + 0.1805P] where P = (Fo2 + 2Fc2)/3
1906 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.64 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
Cl11.39536 (6)0.20927 (6)0.08023 (4)0.01987 (16)
O10.69076 (17)0.31098 (18)0.46559 (11)0.0144 (3)
O21.29992 (18)0.1926 (2)0.61081 (12)0.0182 (3)
O30.7968 (2)0.2432 (3)0.87417 (12)0.0239 (3)
C10.7314 (3)0.2807 (3)0.59818 (15)0.0136 (3)
C20.9290 (3)0.2401 (3)0.65261 (15)0.0131 (3)
C31.1186 (3)0.2214 (3)0.56792 (15)0.0126 (3)
C41.2409 (3)0.2179 (3)0.33066 (15)0.0139 (3)
C51.1898 (3)0.2441 (3)0.19633 (15)0.0148 (3)
C60.9759 (3)0.2980 (3)0.15125 (16)0.0166 (4)
C70.8106 (3)0.3239 (3)0.24213 (16)0.0159 (4)
C81.0736 (3)0.2431 (3)0.42402 (15)0.0120 (3)
C90.8618 (3)0.2926 (3)0.37834 (15)0.0129 (3)
C100.9496 (3)0.2130 (3)0.80066 (16)0.0169 (4)
H10.61350.28810.65800.0163*
H21.38690.18340.35940.0167*
H30.94430.31680.05820.0200*
H40.66430.36250.21230.0191*
H51.09110.16940.84020.0202*
U11U22U33U12U13U23
Cl10.0190 (3)0.0257 (3)0.0136 (3)−0.00517 (16)0.00438 (14)−0.00820 (15)
O10.0101 (5)0.0183 (6)0.0134 (5)−0.0037 (4)−0.0001 (4)−0.0044 (4)
O20.0125 (5)0.0268 (6)0.0158 (6)−0.0066 (5)−0.0007 (4)−0.0074 (5)
O30.0222 (6)0.0358 (8)0.0180 (6)−0.0114 (6)0.0065 (5)−0.0141 (6)
C10.0137 (7)0.0133 (7)0.0130 (7)−0.0036 (6)0.0010 (5)−0.0043 (6)
C20.0133 (7)0.0141 (7)0.0124 (7)−0.0041 (6)0.0004 (6)−0.0056 (6)
C30.0127 (7)0.0115 (7)0.0136 (7)−0.0034 (6)−0.0002 (6)−0.0047 (6)
C40.0137 (7)0.0133 (7)0.0142 (7)−0.0039 (6)0.0003 (6)−0.0044 (6)
C50.0176 (8)0.0133 (7)0.0132 (7)−0.0047 (6)0.0022 (6)−0.0049 (6)
C60.0220 (8)0.0154 (7)0.0118 (7)−0.0064 (6)−0.0017 (6)−0.0031 (6)
C70.0160 (7)0.0164 (7)0.0142 (7)−0.0050 (6)−0.0042 (6)−0.0029 (6)
C80.0132 (7)0.0110 (7)0.0111 (7)−0.0037 (6)−0.0001 (6)−0.0031 (5)
C90.0136 (7)0.0119 (7)0.0124 (7)−0.0038 (6)0.0005 (6)−0.0033 (6)
C100.0189 (8)0.0189 (8)0.0140 (7)−0.0066 (6)0.0010 (6)−0.0068 (6)
Cl1—C51.7377 (17)C4—C81.405 (3)
O1—C11.341 (2)C5—C61.397 (3)
O1—C91.3802 (19)C6—C71.379 (3)
O2—C31.230 (3)C7—C91.393 (3)
O3—C101.210 (2)C8—C91.392 (3)
C1—C21.354 (3)C1—H10.950
C2—C31.457 (3)C4—H20.950
C2—C101.481 (3)C6—H30.950
C3—C81.478 (3)C7—H40.950
C4—C51.383 (3)C10—H50.950
O1···C32.866 (3)C4···H33.2782
O2···C13.578 (3)C5···H43.2649
O2···C42.872 (3)C6···H23.2829
O2···C102.898 (3)C8···H43.2890
O3···C12.812 (3)C9···H13.1907
C1···C73.582 (3)C9···H23.2715
C1···C82.759 (3)C9···H33.2493
C2···C92.769 (3)C10···H12.5487
C4···C72.807 (3)H1···H53.4825
C5···C92.747 (3)H3···H42.3384
C6···C82.795 (3)Cl1···H3xi3.1849
Cl1···O3i3.2840 (16)Cl1···H4vi2.9565
O1···O1ii3.1591 (18)Cl1···H4xi3.4118
O1···O2iii3.1063 (19)Cl1···H5x3.4268
O1···O2iv3.309 (3)Cl1···H5vii3.4313
O1···C1ii3.118 (2)O1···H1ii2.7492
O1···C3v3.589 (3)O1···H2iii2.8618
O1···C4v3.484 (3)O1···H2v3.5281
O1···C8v3.432 (2)O2···H1vi2.5039
O2···O1vi3.1063 (19)O2···H2vii2.6366
O2···O1iv3.309 (3)O3···H3ix2.4552
O2···C1vi3.096 (3)O3···H3v3.5089
O2···C1iv3.543 (3)O3···H4ii3.2371
O2···C4vii3.274 (2)O3···H5xii3.2852
O2···C9iv3.394 (3)C1···H1ii3.4760
O3···Cl1viii3.2840 (16)C1···H2v3.4704
O3···C4iv3.590 (3)C3···H2vii3.4084
O3···C5iv3.436 (3)C4···H1v3.2703
O3···C6ix3.339 (3)C4···H4vi3.3076
C1···O1ii3.118 (2)C5···H1v3.3113
C1···O2iii3.096 (3)C5···H3xi3.2003
C1···O2iv3.543 (3)C5···H4vi3.5285
C1···C4v3.247 (3)C6···H3xi3.0323
C1···C5v3.452 (3)C6···H5x3.5441
C1···C8v3.487 (3)C6···H5v3.4065
C2···C4iv3.592 (3)C7···H1ii3.4852
C2···C5v3.562 (3)C7···H2iii3.2936
C2···C6v3.485 (3)C9···H1ii3.3852
C2···C7v3.507 (3)C9···H2iii3.5013
C2···C8iv3.418 (3)C10···H3ix2.9512
C2···C9v3.580 (3)C10···H3v3.3274
C3···O1v3.589 (3)H1···O1ii2.7492
C3···C3iv3.461 (3)H1···O2iii2.5039
C3···C7v3.541 (3)H1···C1ii3.4760
C3···C8iv3.512 (3)H1···C4v3.2703
C3···C9v3.395 (3)H1···C5v3.3113
C4···O1v3.484 (3)H1···C7ii3.4852
C4···O2vii3.274 (2)H1···C9ii3.3852
C4···O3iv3.590 (3)H1···H1ii3.5933
C4···C1v3.247 (3)H1···H2v3.3433
C4···C2iv3.592 (3)H1···H4ii3.0973
C4···C10iv3.518 (3)H2···O1vi2.8618
C5···O3iv3.436 (3)H2···O1v3.5281
C5···C1v3.452 (3)H2···O2vii2.6366
C5···C2v3.562 (3)H2···C1v3.4704
C5···C10v3.600 (3)H2···C3vii3.4084
C5···C10iv3.568 (3)H2···C7vi3.2936
C6···O3x3.339 (3)H2···C9vi3.5013
C6···C2v3.485 (3)H2···H1v3.3433
C6···C6xi3.536 (3)H2···H2vii3.2073
C6···C10v3.287 (3)H2···H4vi2.6733
C7···C2v3.507 (3)H3···Cl1xi3.1849
C7···C3v3.541 (3)H3···O3x2.4552
C8···O1v3.432 (2)H3···O3v3.5089
C8···C1v3.487 (3)H3···C5xi3.2003
C8···C2iv3.418 (3)H3···C6xi3.0323
C8···C3iv3.512 (3)H3···C10x2.9512
C8···C9v3.512 (3)H3···C10v3.3274
C9···O2iv3.394 (3)H3···H3xi2.7733
C9···C2v3.580 (3)H3···H5x2.7277
C9···C3v3.395 (3)H3···H5v3.2917
C9···C8v3.512 (3)H4···Cl1iii2.9565
C10···C4iv3.518 (3)H4···Cl1xi3.4118
C10···C5v3.600 (3)H4···O3ii3.2371
C10···C5iv3.568 (3)H4···C4iii3.3076
C10···C6v3.287 (3)H4···C5iii3.5285
Cl1···H22.8098H4···H1ii3.0973
Cl1···H32.8018H4···H2iii2.6733
O1···H42.5183H5···Cl1ix3.4268
O2···H22.6171H5···Cl1vii3.4313
O2···H52.6235H5···O3xii3.2852
O3···H12.4841H5···C6ix3.5441
C1···H53.2768H5···C6v3.4065
C3···H13.2936H5···H3ix2.7277
C3···H22.6894H5···H3v3.2917
C3···H52.7009
C1—O1—C9118.51 (13)C4—C8—C9118.86 (15)
O1—C1—C2124.50 (14)O1—C9—C7116.07 (15)
C1—C2—C3120.89 (15)O1—C9—C8122.03 (15)
C1—C2—C10118.68 (14)C7—C9—C8121.89 (15)
C3—C2—C10120.43 (15)O3—C10—C2123.81 (16)
O2—C3—C2123.55 (15)O1—C1—H1117.750
O2—C3—C8122.50 (14)C2—C1—H1117.752
C2—C3—C8113.94 (14)C5—C4—H2120.520
C5—C4—C8118.97 (15)C8—C4—H2120.513
Cl1—C5—C4119.56 (13)C5—C6—H3120.086
Cl1—C5—C6118.90 (13)C7—C6—H3120.081
C4—C5—C6121.54 (15)C6—C7—H4120.563
C5—C6—C7119.83 (16)C9—C7—H4120.557
C6—C7—C9118.88 (16)O3—C10—H5118.090
C3—C8—C4121.17 (15)C2—C10—H5118.097
C3—C8—C9119.97 (14)
C1—O1—C9—C7179.49 (13)C8—C4—C5—Cl1−178.97 (13)
C1—O1—C9—C80.2 (2)C8—C4—C5—C61.0 (3)
C9—O1—C1—C22.4 (3)H2—C4—C5—Cl11.0
C9—O1—C1—H1−177.6H2—C4—C5—C6−179.0
O1—C1—C2—C3−1.4 (3)H2—C4—C8—C31.3
O1—C1—C2—C10179.14 (13)H2—C4—C8—C9−179.7
H1—C1—C2—C3178.6Cl1—C5—C6—C7179.23 (11)
H1—C1—C2—C10−0.9Cl1—C5—C6—H3−0.8
C1—C2—C3—O2177.29 (15)C4—C5—C6—C7−0.7 (3)
C1—C2—C3—C8−2.0 (2)C4—C5—C6—H3179.3
C1—C2—C10—O3−6.6 (3)C5—C6—C7—C9−0.8 (3)
C1—C2—C10—H5173.4C5—C6—C7—H4179.1
C3—C2—C10—O3173.91 (15)H3—C6—C7—C9179.1
C3—C2—C10—H5−6.1H3—C6—C7—H4−0.9
C10—C2—C3—O2−3.3 (3)C6—C7—C9—O1−177.08 (14)
C10—C2—C3—C8177.49 (13)C6—C7—C9—C82.2 (3)
O2—C3—C8—C44.1 (3)H4—C7—C9—O12.9
O2—C3—C8—C9−174.93 (14)H4—C7—C9—C8−177.8
C2—C3—C8—C4−176.66 (13)C3—C8—C9—O1−3.7 (3)
C2—C3—C8—C94.3 (2)C3—C8—C9—C7177.13 (13)
C5—C4—C8—C3−178.70 (13)C4—C8—C9—O1177.30 (14)
C5—C4—C8—C90.3 (3)C4—C8—C9—C7−1.9 (3)
  6 in total

1.  A short history of SHELX.

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3.  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

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

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Journal:  J Chem Inf Model       Date:  2013-11-13       Impact factor: 4.956

5.  6,8-Di-chloro-4-oxochromene-3-carbalde-hyde.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-08-14

6.  6,8-Di-bromo-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-03-15
  6 in total
  10 in total

1.  Crystal structure of 6-bromo-7-fluoro-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-06-27

2.  Crystal structure of 6,7-di-chloro-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-08-12

3.  6-Chloro-8-nitro-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-12

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

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-16

5.  6-Fluoro-4-oxo-4H-chromene-3-carbalde-hyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-18

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

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

7.  8-Chloro-4-oxo-4H-chromene-3-carbaldehyde.

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

8.  6-Chloro-7-fluoro-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-06-25

9.  6-Chloro-7-methyl-4-oxo-4H-chromene-3-carbaldehyde.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-06-21

10.  7-Chloro-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
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  10 in total

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