Literature DB >> 25161585

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

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C11H7ClO3, a chlorinated and methyl-ated 3-formyl-chromone derivative, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.0670 Å), with the largest deviation from the least-squares plane [0.2349 (17) Å] being for the pyran carbonyl O atom. In the crystal, mol-ecules are linked through π-π stacking inter-actions along the a axis [centroid-centroid distance between the pyran rings = 3.824 (6) Å] and two stacks are connected by type I halogen-halogen inter-actions between the Cl atoms [Cl⋯Cl = 3.397 (3) Å].

Entities:  

Keywords:  crystal structure

Year:  2014        PMID： 25161585      PMCID： PMC4120566          DOI： 10.1107/S1600536814014226

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: Metrangolo & Resnati (2014 ▶); Mukherjee & Desiraju (2014 ▶).

Experimental

Crystal data

C11H7ClO3 M = 222.63 Triclinic, a = 3.824 (6) Å b = 6.111 (9) Å c = 19.962 (10) Å α = 81.83 (7)° β = 88.82 (7)° γ = 87.04 (12)° V = 461.1 (10) Å3 Z = 2 Mo Kα radiation μ = 0.39 mm−1 T = 100 K 0.45 × 0.20 × 0.10 mm

Data collection

Rigaku AFC-7R diffractometer 2677 measured reflections 2092 independent reflections 1784 reflections with F 2 > 2σ(F 2) R int = 0.076 3 standard reflections every 150 reflections intensity decay: −0.3%

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.094 S = 1.08 2092 reflections 137 parameters H-atom parameters constrained Δρmax = 0.43 e Å−3 Δρmin = −0.44 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/S1600536814014226/tk5320sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014226/tk5320Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814014226/tk5320Isup3.cml CCDC reference: 1008807 Additional supporting information: crystallographic information; 3D view; checkCIF report
C11H7ClO3Z = 2
Mr = 222.63F(000) = 228.00
Triclinic, P1Dx = 1.603 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 3.824 (6) ÅCell parameters from 25 reflections
b = 6.111 (9) Åθ = 15.1–17.5°
c = 19.962 (10) ŵ = 0.39 mm−1
α = 81.83 (7)°T = 100 K
β = 88.82 (7)°Plate, colorless
γ = 87.04 (12)°0.45 × 0.20 × 0.10 mm
V = 461.1 (10) Å3
Rigaku AFC-7R diffractometerθmax = 27.5°
ω–2θ scansh = −4→2
2677 measured reflectionsk = −7→7
2092 independent reflectionsl = −25→25
1784 reflections with F2 > 2σ(F2)3 standard reflections every 150 reflections
Rint = 0.076 intensity decay: −0.3%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0479P)2 + 0.2265P] where P = (Fo2 + 2Fc2)/3
2092 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.44 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
Cl10.17920 (11)0.14364 (6)0.056454 (19)0.01599 (13)
O10.4150 (4)0.24855 (18)0.33907 (6)0.0147 (3)
O2−0.0788 (4)−0.30118 (19)0.30226 (6)0.0175 (3)
O30.2039 (4)−0.2523 (3)0.49681 (6)0.0257 (3)
C10.3352 (5)0.0873 (3)0.38908 (8)0.0149 (4)
C20.1817 (5)−0.1014 (3)0.38028 (8)0.0143 (4)
C30.0832 (5)−0.1417 (3)0.31299 (8)0.0125 (3)
C40.1395 (4)0.0114 (3)0.19037 (8)0.0124 (3)
C50.2401 (4)0.1770 (3)0.14057 (8)0.0125 (3)
C60.3901 (4)0.3707 (3)0.15567 (8)0.0123 (3)
C70.4419 (4)0.3892 (3)0.22300 (8)0.0131 (3)
C80.1912 (4)0.0316 (3)0.25829 (8)0.0117 (3)
C90.3461 (4)0.2198 (3)0.27341 (8)0.0122 (3)
C100.4919 (5)0.5510 (3)0.10037 (9)0.0158 (4)
C110.1133 (5)−0.2676 (3)0.43982 (9)0.0185 (4)
H10.39040.10680.43400.0179*
H20.0357−0.11560.17860.0149*
H30.54260.51710.23490.0157*
H4A0.60250.66730.12030.0190*
H5B0.28240.61390.07580.0190*
H6C0.65710.48930.06900.0190*
H7−0.0088−0.39400.43310.0222*
U11U22U33U12U13U23
Cl10.0226 (3)0.0153 (2)0.0106 (2)−0.00165 (14)−0.00239 (13)−0.00318 (13)
O10.0210 (6)0.0146 (6)0.0093 (6)−0.0054 (5)−0.0015 (5)−0.0026 (4)
O20.0222 (7)0.0151 (6)0.0160 (6)−0.0074 (5)−0.0018 (5)−0.0024 (5)
O30.0382 (8)0.0262 (7)0.0129 (7)−0.0108 (6)−0.0028 (6)0.0009 (5)
C10.0178 (8)0.0169 (8)0.0102 (8)−0.0016 (6)−0.0000 (6)−0.0019 (6)
C20.0161 (8)0.0148 (8)0.0121 (8)−0.0014 (6)0.0000 (6)−0.0018 (6)
C30.0119 (7)0.0129 (7)0.0130 (8)−0.0000 (6)−0.0002 (6)−0.0030 (6)
C40.0123 (8)0.0113 (7)0.0142 (8)−0.0005 (6)−0.0012 (6)−0.0039 (6)
C50.0125 (8)0.0140 (7)0.0116 (7)0.0012 (6)−0.0012 (6)−0.0037 (6)
C60.0101 (7)0.0113 (7)0.0151 (8)0.0011 (6)−0.0000 (6)−0.0015 (6)
C70.0128 (8)0.0108 (7)0.0160 (8)−0.0011 (6)−0.0004 (6)−0.0032 (6)
C80.0119 (8)0.0110 (7)0.0125 (8)−0.0000 (6)−0.0016 (6)−0.0026 (6)
C90.0124 (8)0.0136 (7)0.0114 (8)0.0001 (6)−0.0017 (6)−0.0044 (6)
C100.0198 (8)0.0120 (7)0.0152 (8)−0.0021 (6)0.0010 (6)0.0001 (6)
C110.0237 (9)0.0177 (8)0.0143 (8)−0.0054 (7)−0.0004 (7)−0.0015 (6)
Cl1—C51.7418 (19)C6—C71.384 (3)
O1—C11.341 (3)C6—C101.505 (3)
O1—C91.379 (3)C7—C91.395 (3)
O2—C31.228 (3)C8—C91.394 (3)
O3—C111.214 (3)C1—H10.950
C1—C21.355 (3)C4—H20.950
C2—C31.460 (3)C7—H30.950
C2—C111.478 (3)C10—H4A0.980
C3—C81.477 (3)C10—H5B0.980
C4—C51.378 (3)C10—H6C0.980
C4—C81.398 (3)C11—H70.950
C5—C61.414 (3)
Cl1···C103.061 (5)O3···H7iv3.3646
O1···C32.874 (5)O3···H7viii2.5400
O2···C13.580 (5)C1···H7ii3.5865
O2···C42.865 (4)C2···H1vii3.4323
O2···C112.895 (3)C2···H7iv3.5942
O3···C12.825 (4)C3···H3v3.5438
C1···C73.584 (4)C3···H3vi3.2093
C1···C82.751 (3)C4···H2iv3.4855
C2···C92.772 (4)C4···H3vi3.3323
C4···C72.797 (5)C4···H4Av3.4637
C5···C92.742 (3)C4···H4Avi3.1405
C6···C82.821 (4)C4···H5Bvi3.5800
Cl1···Cl1i3.397 (3)C5···H2iv3.4899
O1···O2ii3.259 (5)C5···H4Avi3.4169
O1···O2iii3.432 (5)C5···H6Cvii3.0939
O1···C2iv3.578 (6)C6···H2ii3.4420
O1···C3iv3.487 (6)C6···H4Avii3.4668
O2···O1v3.432 (5)C6···H6Cvii3.3186
O2···O1vi3.259 (5)C7···H2ii3.3414
O2···C2vii3.452 (5)C7···H3vii3.4983
O2···C3vii3.313 (6)C8···H3vi3.4446
O2···C7v3.282 (4)C9···H3vii3.5296
O2···C7vi3.222 (5)C10···H2ii3.1715
O2···C8vii3.422 (6)C10···H2iii3.5202
O2···C9vi3.389 (5)C10···H4Avii3.4653
O3···O3viii3.462 (5)C10···H5Biv3.0874
O3···O3ix3.400 (5)C10···H6Cvii3.3170
O3···C1ix3.271 (4)C10···H6Cxii3.4850
O3···C1x3.212 (4)C11···H1vii3.4892
O3···C11viii3.306 (5)C11···H1ix3.3664
C1···O3ix3.271 (4)C11···H1x3.4654
C1···O3x3.212 (4)C11···H7iv3.4101
C1···C2iv3.390 (6)C11···H7viii3.0703
C1···C3iv3.530 (5)H1···O3ix2.8065
C2···O1vii3.578 (6)H1···O3x2.3848
C2···O2iv3.452 (5)H1···C2iv3.4323
C2···C1vii3.390 (6)H1···C11iv3.4892
C3···O1vii3.487 (6)H1···C11ix3.3664
C3···O2iv3.313 (6)H1···C11x3.4654
C3···C1vii3.530 (5)H1···H1x2.8906
C3···C9vii3.522 (6)H1···H7ii3.3381
C4···C6vii3.537 (6)H2···C4vii3.4855
C4···C7vii3.548 (6)H2···C5vii3.4899
C5···C6vii3.424 (6)H2···C6vi3.4420
C5···C10vii3.599 (6)H2···C7vi3.3414
C6···C4iv3.537 (6)H2···C10v3.5202
C6···C5iv3.424 (6)H2···C10vi3.1715
C7···O2ii3.222 (5)H2···H3v3.0807
C7···O2iii3.282 (4)H2···H3vi2.9969
C7···C4iv3.548 (6)H2···H4Av2.5702
C7···C8iv3.533 (6)H2···H4Avi2.8020
C8···O2iv3.422 (6)H2···H5Bvi2.9247
C8···C7vii3.533 (6)H3···O2ii2.9512
C8···C9vii3.396 (6)H3···O2iii2.4107
C9···O2ii3.389 (5)H3···C3ii3.2093
C9···C3iv3.522 (6)H3···C3iii3.5438
C9···C8iv3.396 (6)H3···C4ii3.3323
C10···C5iv3.599 (6)H3···C7iv3.4983
C11···O3viii3.306 (5)H3···C8ii3.4446
C11···C11viii3.581 (5)H3···C9iv3.5296
Cl1···H22.7736H3···H2ii2.9969
Cl1···H5B3.0008H3···H2iii3.0807
Cl1···H6C2.9039H4A···Cl1ii3.3558
O1···H32.5156H4A···C4ii3.1405
O2···H22.6042H4A···C4iii3.4637
O2···H72.6084H4A···C5ii3.4169
O3···H12.4980H4A···C6iv3.4668
C1···H73.2820H4A···C10iv3.4653
C3···H13.2957H4A···H2ii2.8020
C3···H22.6739H4A···H2iii2.5702
C3···H72.6867H4A···H5Biv2.7486
C5···H33.2635H5B···Cl1ii3.2097
C5···H4A3.3351H5B···Cl1xi3.3310
C5···H5B2.8070H5B···Cl1xii3.5195
C5···H6C2.7698H5B···C4ii3.5800
C6···H23.2984H5B···C10vii3.0874
C7···H4A2.5561H5B···H2ii2.9247
C7···H5B3.1190H5B···H4Avii2.7486
C7···H6C3.1491H5B···H6Cvii2.5591
C8···H33.2892H5B···H6Cxii3.0471
C9···H13.1874H6C···Cl1iv2.8645
C9···H23.2616H6C···Cl1xii3.1901
C10···H32.6736H6C···C5iv3.0939
C11···H12.5574H6C···C6iv3.3186
H1···H73.4925H6C···C10iv3.3170
H3···H4A2.3514H6C···C10xii3.4850
H3···H5B3.3096H6C···H5Biv2.5591
H3···H6C3.3584H6C···H5Bxii3.0471
Cl1···H4Avi3.3558H6C···H6Cxii3.0105
Cl1···H5Bvi3.2097H7···O1vi3.4049
Cl1···H5Bxi3.3310H7···O3vii3.3646
Cl1···H5Bxii3.5195H7···O3viii2.5400
Cl1···H6Cvii2.8645H7···C1vi3.5865
Cl1···H6Cxii3.1901H7···C2vii3.5942
O1···H7ii3.4049H7···C11vii3.4101
O2···H3v2.4107H7···C11viii3.0703
O2···H3vi2.9512H7···H1vi3.3381
O3···H1ix2.8065H7···H7viii2.7996
O3···H1x2.3848
C1—O1—C9118.32 (15)O1—C9—C7116.26 (16)
O1—C1—C2124.81 (17)O1—C9—C8121.84 (15)
C1—C2—C3120.85 (15)C7—C9—C8121.90 (17)
C1—C2—C11119.27 (17)O3—C11—C2123.93 (18)
C3—C2—C11119.87 (17)O1—C1—H1117.595
O2—C3—C2123.93 (15)C2—C1—H1117.592
O2—C3—C8122.62 (17)C5—C4—H2120.213
C2—C3—C8113.45 (16)C8—C4—H2120.226
C5—C4—C8119.56 (17)C6—C7—H3120.052
Cl1—C5—C4118.24 (15)C9—C7—H3120.055
Cl1—C5—C6119.54 (13)C6—C10—H4A109.463
C4—C5—C6122.22 (17)C6—C10—H5B109.471
C5—C6—C7117.93 (15)C6—C10—H6C109.471
C5—C6—C10121.19 (17)H4A—C10—H5B109.473
C7—C6—C10120.87 (16)H4A—C10—H6C109.475
C6—C7—C9119.89 (17)H5B—C10—H6C109.474
C3—C8—C4121.00 (16)O3—C11—H7118.044
C3—C8—C9120.54 (16)C2—C11—H7118.029
C4—C8—C9118.46 (15)
C1—O1—C9—C7−178.36 (12)H2—C4—C5—C6178.9
C1—O1—C9—C81.3 (2)H2—C4—C8—C3−0.6
C9—O1—C1—C2−1.9 (3)H2—C4—C8—C9179.6
C9—O1—C1—H1178.1Cl1—C5—C6—C7−178.56 (10)
O1—C1—C2—C3−1.1 (3)Cl1—C5—C6—C101.2 (2)
O1—C1—C2—C11179.01 (13)C4—C5—C6—C71.3 (3)
H1—C1—C2—C3178.9C4—C5—C6—C10−178.89 (13)
H1—C1—C2—C11−1.0C5—C6—C7—C9−0.1 (3)
C1—C2—C3—O2−174.55 (15)C5—C6—C7—H3179.9
C1—C2—C3—C84.3 (2)C5—C6—C10—H4A−176.9
C1—C2—C11—O3−4.2 (3)C5—C6—C10—H5B63.1
C1—C2—C11—H7175.8C5—C6—C10—H6C−56.9
C3—C2—C11—O3175.88 (15)C7—C6—C10—H4A2.8
C3—C2—C11—H7−4.1C7—C6—C10—H5B−117.1
C11—C2—C3—O25.3 (3)C7—C6—C10—H6C122.8
C11—C2—C3—C8−175.85 (13)C10—C6—C7—C9−179.90 (13)
O2—C3—C8—C4−5.7 (3)C10—C6—C7—H30.1
O2—C3—C8—C9174.08 (14)C6—C7—C9—O1178.34 (13)
C2—C3—C8—C4175.51 (13)C6—C7—C9—C8−1.3 (3)
C2—C3—C8—C9−4.8 (2)H3—C7—C9—O1−1.7
C5—C4—C8—C3179.37 (13)H3—C7—C9—C8178.7
C5—C4—C8—C9−0.4 (3)C3—C8—C9—O12.2 (3)
C8—C4—C5—Cl1178.80 (12)C3—C8—C9—C7−178.17 (13)
C8—C4—C5—C6−1.1 (3)C4—C8—C9—O1−178.08 (13)
H2—C4—C5—Cl1−1.2C4—C8—C9—C71.6 (3)
  9 in total

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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.

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

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

7.  6,8-Di-chloro-4-oxochromene-3-carbalde-hyde.

Authors:  Yoshinobu Ishikawa; Yuya Motohashi
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8.  Halogen bonds in some dihalogenated phenols: applications to crystal engineering.

Authors:  Arijit Mukherjee; Gautam R Desiraju
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9.  Type II halogen···halogen contacts are halogen bonds.

Authors:  Pierangelo Metrangolo; Giuseppe Resnati
Journal:  IUCrJ       Date:  2013-12-31       Impact factor: 4.769
  9 in total

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