Literature DB >> 25161540

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

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H5ClO3, a chlorinated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. deviation = 0.032 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.0598 (14) Å] being for a pyran-ring C 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 = 3.566 (2) Å].

Entities:  

Year:  2014        PMID： 25161540      PMCID： PMC4120543          DOI： 10.1107/S1600536814012483

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: Fumagalli et al. (2012 ▶). For van der Waals radii; see: Bondi (1964 ▶). For halogen bonding, see: Auffinger et al. (2004 ▶); Metrangolo et al. (2005 ▶); Wilcken et al. (2013 ▶); Sirimulla et al. (2013 ▶).

Experimental

Crystal data

C10H5ClO3 M = 208.60 Triclinic, a = 6.9436 (15) Å b = 7.1539 (17) Å c = 9.165 (2) Å α = 102.049 (19)° β = 103.403 (17)° γ = 100.650 (19)° V = 419.89 (18) Å3 Z = 2 Mo Kα radiation μ = 0.43 mm−1 T = 100 K 0.38 × 0.25 × 0.10 mm

Data collection

Rigaku AFC-7R diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.902, T max = 0.958 2376 measured reflections 1932 independent reflections 1750 reflections with F 2 > 2σ(F 2) R int = 0.011 3 standard reflections every 150 reflections intensity decay: −0.039%

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.075 S = 1.09 1932 reflections 127 parameters H-atom parameters constrained Δρmax = 0.34 e Å−3 Δρmin = −0.26 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/S1600536814012483/zl2591sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012483/zl2591Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814012483/zl2591Isup3.cml Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H5ClO3Z = 2
Mr = 208.60F(000) = 212.00
Triclinic, P1Dx = 1.650 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 6.9436 (15) ÅCell parameters from 25 reflections
b = 7.1539 (17) Åθ = 15.1–17.5°
c = 9.165 (2) ŵ = 0.43 mm−1
α = 102.049 (19)°T = 100 K
β = 103.403 (17)°Plate, yellow
γ = 100.650 (19)°0.38 × 0.25 × 0.10 mm
V = 419.89 (18) Å3
Rigaku AFC-7R diffractometerRint = 0.011
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)h = −5→9
Tmin = 0.902, Tmax = 0.958k = −9→9
2376 measured reflectionsl = −11→11
1932 independent reflections3 standard reflections every 150 reflections
1750 reflections with F2 > 2σ(F2) intensity decay: −0.039%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0344P)2 + 0.1939P] where P = (Fo2 + 2Fc2)/3
1932 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.26 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
Cl10.28721 (5)0.37563 (5)1.29528 (4)0.02580 (11)
O10.21886 (13)0.15266 (13)0.97744 (10)0.0187 (2)
O20.63950 (15)0.10011 (16)0.73295 (11)0.0279 (3)
O30.04173 (16)−0.20711 (16)0.52591 (12)0.0297 (3)
C10.16551 (19)0.04262 (19)0.82917 (14)0.0189 (3)
C20.29522 (19)0.01959 (19)0.74169 (14)0.0184 (3)
C30.51287 (19)0.11867 (19)0.80487 (14)0.0184 (3)
C40.76947 (18)0.35541 (19)1.04110 (15)0.0180 (3)
C50.81834 (19)0.47543 (19)1.19027 (15)0.0189 (3)
C60.66911 (19)0.48195 (18)1.26931 (14)0.0183 (3)
C70.47153 (19)0.37036 (19)1.19772 (14)0.0176 (3)
C80.56861 (18)0.24423 (18)0.96597 (14)0.0161 (3)
C90.41997 (18)0.25375 (17)1.04458 (14)0.0157 (3)
C100.2152 (2)−0.1091 (2)0.58050 (15)0.0236 (3)
H10.0257−0.02380.78280.0227*
H20.87250.34810.98910.0216*
H30.3054−0.11450.51690.0284*
H40.95360.55371.23920.0226*
H50.70350.56321.37240.0220*
U11U22U33U12U13U23
Cl10.01652 (16)0.0338 (2)0.02036 (17)−0.00018 (12)0.00735 (12)−0.00404 (13)
O10.0116 (4)0.0215 (5)0.0159 (5)−0.0032 (4)0.0015 (4)−0.0009 (4)
O20.0227 (5)0.0370 (6)0.0190 (5)−0.0015 (5)0.0093 (4)0.0010 (4)
O30.0252 (6)0.0309 (6)0.0200 (5)−0.0059 (5)0.0003 (4)−0.0027 (4)
C10.0158 (6)0.0182 (6)0.0159 (6)−0.0030 (5)−0.0003 (5)0.0014 (5)
C20.0187 (6)0.0174 (6)0.0138 (6)−0.0019 (5)0.0009 (5)0.0026 (5)
C30.0182 (6)0.0197 (6)0.0144 (6)−0.0004 (5)0.0032 (5)0.0041 (5)
C40.0134 (6)0.0200 (6)0.0183 (6)−0.0005 (5)0.0038 (5)0.0047 (5)
C50.0132 (6)0.0200 (6)0.0185 (6)−0.0012 (5)0.0004 (5)0.0039 (5)
C60.0173 (6)0.0177 (6)0.0147 (6)0.0006 (5)0.0005 (5)0.0006 (5)
C70.0147 (6)0.0196 (6)0.0165 (6)0.0019 (5)0.0044 (5)0.0026 (5)
C80.0147 (6)0.0169 (6)0.0140 (6)−0.0002 (5)0.0025 (5)0.0039 (5)
C90.0116 (6)0.0154 (6)0.0157 (6)−0.0011 (5)0.0004 (5)0.0026 (5)
C100.0248 (7)0.0257 (7)0.0138 (6)−0.0017 (6)0.0024 (5)0.0014 (5)
Cl1—C71.7243 (16)C4—C81.4029 (16)
O1—C11.3475 (15)C5—C61.397 (2)
O1—C91.3763 (14)C6—C71.3817 (17)
O2—C31.2250 (19)C7—C91.4006 (17)
O3—C101.2061 (16)C8—C91.393 (2)
C1—C21.347 (2)C1—H10.950
C2—C31.4658 (17)C4—H20.950
C2—C101.4836 (17)C5—H40.950
C3—C81.4797 (17)C6—H50.950
C4—C51.3815 (18)C10—H30.950
Cl1···O12.8973 (12)C3···H13.2929
O1···C32.8719 (19)C3···H22.6746
O2···C13.574 (2)C3···H32.7084
O2···C42.8604 (17)C4···H53.2636
O2···C102.9089 (18)C6···H23.2648
O3···C12.8120 (17)C7···H43.2634
C1···C73.5981 (19)C8···H43.2730
C1···C82.7591 (18)C9···H13.1860
C2···C92.7695 (18)C9···H23.2689
C4···C72.783 (2)C9···H53.2672
C5···C92.7806 (18)C10···H12.5482
C6···C82.7921 (18)H1···H33.4825
Cl1···O2i3.4989 (15)H2···H42.3282
Cl1···O3ii3.3012 (15)H4···H52.3459
Cl1···C5iii3.4247 (16)Cl1···H1ii2.8415
O1···O1ii3.5617 (16)Cl1···H2iii3.4669
O1···O2i3.5683 (17)Cl1···H4iii2.8395
O1···C3i3.5282 (19)Cl1···H5x2.9688
O1···C4iv3.5456 (19)O1···H1ii3.2499
O1···C5iv3.359 (2)O1···H2iii3.0086
O1···C8i3.5096 (19)O1···H4iv3.3704
O2···Cl1i3.4989 (15)O2···H1viii2.9439
O2···O1i3.5683 (17)O2···H3v2.4269
O2···C7i3.534 (2)O2···H4xi3.3161
O2···C9i3.591 (2)O3···H1vi3.5460
O2···C10v3.267 (2)O3···H4vii2.6830
O3···Cl1ii3.3012 (15)O3···H5vii2.5041
O3···O3vi3.2307 (19)O3···H5i3.5184
O3···C5vii3.2551 (18)C1···H2iii3.5714
O3···C6vii3.1687 (17)C1···H2i3.5400
O3···C6i3.560 (2)C1···H4iv3.2889
O3···C10vi3.295 (2)C2···H5iv3.3614
C1···C4i3.371 (3)C3···H3v3.4629
C1···C5iv3.472 (3)C3···H5iv3.4282
C1···C8i3.542 (3)C4···H1i3.4694
C2···C6iv3.553 (3)C4···H2xi3.0614
C2···C7i3.552 (3)C5···H2xi3.2259
C2···C9i3.578 (2)C6···H3i3.5976
C3···O1i3.5282 (19)C10···H4vii3.3912
C3···C6iv3.460 (3)C10···H5i3.4945
C3···C7i3.515 (3)H1···Cl1ii2.8415
C3···C9i3.304 (3)H1···O1ii3.2499
C4···O1iv3.5456 (19)H1···O2iii2.9439
C4···C1i3.371 (3)H1···O3vi3.5460
C4···C7iv3.570 (3)H1···C4i3.4694
C4···C9iv3.459 (3)H1···H2iii3.4159
C5···Cl1viii3.4247 (16)H1···H2i3.4928
C5···O1iv3.359 (2)H1···H3vi3.5853
C5···O3ix3.2551 (18)H1···H4iv3.3899
C5···C1iv3.472 (3)H2···Cl1viii3.4669
C5···C9iv3.521 (2)H2···O1viii3.0086
C6···O3ix3.1687 (17)H2···C1viii3.5714
C6···O3i3.560 (2)H2···C1i3.5400
C6···C2iv3.553 (3)H2···C4xi3.0614
C6···C3iv3.460 (3)H2···C5xi3.2259
C6···C8iv3.538 (2)H2···H1viii3.4159
C6···C10i3.387 (3)H2···H1i3.4928
C7···O2i3.534 (2)H2···H2xi2.4762
C7···C2i3.552 (3)H2···H4xi2.7931
C7···C3i3.515 (3)H3···O2v2.4269
C7···C4iv3.570 (3)H3···C3v3.4629
C7···C8iv3.427 (3)H3···C6i3.5976
C8···O1i3.5096 (19)H3···H1vi3.5853
C8···C1i3.542 (3)H3···H3v3.0081
C8···C6iv3.538 (2)H3···H4vii3.2450
C8···C7iv3.427 (3)H3···H5i3.5572
C8···C9i3.560 (2)H4···Cl1viii2.8395
C8···C9iv3.600 (2)H4···O1iv3.3704
C9···O2i3.591 (2)H4···O2xi3.3161
C9···C2i3.578 (2)H4···O3ix2.6830
C9···C3i3.304 (3)H4···C1iv3.2889
C9···C4iv3.459 (3)H4···C10ix3.3912
C9···C5iv3.521 (2)H4···H1iv3.3899
C9···C8i3.560 (2)H4···H2xi2.7931
C9···C8iv3.600 (2)H4···H3ix3.2450
C10···O2v3.267 (2)H5···Cl1x2.9688
C10···O3vi3.295 (2)H5···O3ix2.5041
C10···C6i3.387 (3)H5···O3i3.5184
Cl1···H52.8072H5···C2iv3.3614
O2···H22.5915H5···C3iv3.4282
O2···H32.6355H5···C10i3.4945
O3···H12.4818H5···H3i3.5572
C1···H33.2782
C1—O1—C9118.02 (11)C4—C8—C9119.19 (11)
O1—C1—C2125.01 (11)O1—C9—C7117.14 (12)
C1—C2—C3120.64 (11)O1—C9—C8122.57 (10)
C1—C2—C10119.09 (11)C7—C9—C8120.29 (11)
C3—C2—C10120.26 (13)O3—C10—C2123.51 (15)
O2—C3—C2123.90 (11)O1—C1—H1117.494
O2—C3—C8122.20 (11)C2—C1—H1117.497
C2—C3—C8113.90 (12)C5—C4—H2119.817
C5—C4—C8120.37 (13)C8—C4—H2119.815
C4—C5—C6120.11 (11)C4—C5—H4119.941
C5—C6—C7120.09 (11)C6—C5—H4119.944
Cl1—C7—C6120.35 (10)C5—C6—H5119.956
Cl1—C7—C9119.75 (10)C7—C6—H5119.956
C6—C7—C9119.90 (13)O3—C10—H3118.246
C3—C8—C4121.00 (13)C2—C10—H3118.242
C3—C8—C9119.81 (10)
C1—O1—C9—C7178.77 (11)C8—C4—C5—C62.1 (3)
C1—O1—C9—C8−0.80 (18)C8—C4—C5—H4−177.9
C9—O1—C1—C21.7 (2)H2—C4—C5—C6−177.9
C9—O1—C1—H1−178.3H2—C4—C5—H42.1
O1—C1—C2—C3−0.5 (3)H2—C4—C8—C3−1.5
O1—C1—C2—C10179.02 (12)H2—C4—C8—C9178.9
H1—C1—C2—C3179.5C4—C5—C6—C7−0.9 (2)
H1—C1—C2—C10−1.0C4—C5—C6—H5179.1
C1—C2—C3—O2178.13 (14)H4—C5—C6—C7179.1
C1—C2—C3—C8−1.5 (2)H4—C5—C6—H5−0.9
C1—C2—C10—O3−5.7 (3)C5—C6—C7—Cl1179.30 (12)
C1—C2—C10—H3174.3C5—C6—C7—C9−1.3 (2)
C3—C2—C10—O3173.77 (13)H5—C6—C7—Cl1−0.7
C3—C2—C10—H3−6.2H5—C6—C7—C9178.7
C10—C2—C3—O2−1.3 (3)Cl1—C7—C9—O12.11 (18)
C10—C2—C3—C8179.06 (12)Cl1—C7—C9—C8−178.31 (9)
O2—C3—C8—C43.0 (3)C6—C7—C9—O1−177.27 (12)
O2—C3—C8—C9−177.39 (13)C6—C7—C9—C82.3 (2)
C2—C3—C8—C4−177.42 (12)C3—C8—C9—O1−1.2 (2)
C2—C3—C8—C92.21 (19)C3—C8—C9—C7179.27 (11)
C5—C4—C8—C3178.54 (12)C4—C8—C9—O1178.46 (12)
C5—C4—C8—C9−1.1 (2)C4—C8—C9—C7−1.1 (2)
  8 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
Journal:  Acc Chem Res       Date:  2005-05       Impact factor: 22.384

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.  Affinity and activity profiling of unichiral 8-substituted 1,4-benzodioxane analogues of WB4101 reveals a potent and selective α1B-adrenoceptor antagonist.

Authors:  Laura Fumagalli; Marco Pallavicini; Roberta Budriesi; Marco Gobbi; Valentina Straniero; Michael Zagami; Giuseppe Chiodini; Cristiano Bolchi; Alberto Chiarini; Matteo Micucci; Ermanno Valoti
Journal:  Eur J Med Chem       Date:  2012-10-16       Impact factor: 6.514

6.  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

7.  6-Chloro-4-oxo-4H-chromene-3-carb-aldehyde.

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

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

Authors:  Yoshinobu Ishikawa; Yuya Motohashi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-08-14
  8 in total
  2 in total

1.  Crystal structure of 7,8-di-chloro-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-07-08

2.  7-Chloro-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-07-02
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.