Literature DB >> 25249886

7-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 = 0.0592 Å for all non-H atoms), with the largest deviation from the least-squares plane [0.1792 (19) Å] being for the chromone-ring carbonyl O atom. In the crystal, mol-ecules are linked through C-H⋯O hydrogen bonds to form tetrads, which are assembled by stacking inter-actions [centroid-centroid distance between the pyran rings = 3.823 (3) Å] and van der Waals contacts between the Cl atoms [Cl⋯Cl = 3.4483 (16) Å and C-Cl⋯Cl = 171.73 (7)°] into a three-dimensional architecture.

Entities:  

Keywords:  crystal structure

Year:  2014        PMID： 25249886      PMCID： PMC4158550          DOI： 10.1107/S1600536814014925

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


Related literature

For related structures, see: Ishikawa & Motohashi (2013 ▶); Ishikawa (2014a ▶,b ▶). 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

C10H5ClO3 M = 208.60 Triclinic, a = 3.823 (2) Å b = 5.973 (3) Å c = 18.386 (8) Å α = 85.99 (4)° β = 87.74 (4)° γ = 86.58 (4)° V = 417.8 (4) Å3 Z = 2 Mo Kα radiation μ = 0.43 mm−1 T = 100 K 0.42 × 0.25 × 0.08 mm

Data collection

Rigaku AFC-7R diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.865, T max = 0.966 2429 measured reflections 1899 independent reflections 1690 reflections with F 2 > 2σ(F 2) R int = 0.050 3 standard reflections every 150 reflections intensity decay: −1.1%

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.104 S = 1.10 1899 reflections 127 parameters H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.50 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/S1600536814014925/tk5323sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014925/tk5323Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814014925/tk5323Isup3.cml CCDC reference: 1010095 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H5ClO3Z = 2
Mr = 208.60F(000) = 212.00
Triclinic, P1Dx = 1.658 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 3.823 (2) ÅCell parameters from 25 reflections
b = 5.973 (3) Åθ = 15.2–17.0°
c = 18.386 (8) ŵ = 0.43 mm−1
α = 85.99 (4)°T = 100 K
β = 87.74 (4)°Plate, yellow
γ = 86.58 (4)°0.42 × 0.25 × 0.08 mm
V = 417.8 (4) Å3
Rigaku AFC-7R diffractometerRint = 0.050
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)h = −4→2
Tmin = 0.865, Tmax = 0.966k = −7→7
2429 measured reflectionsl = −23→23
1899 independent reflections3 standard reflections every 150 reflections
1690 reflections with F2 > 2σ(F2) intensity decay: −1.1%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0425P)2 + 0.5019P] where P = (Fo2 + 2Fc2)/3
1899 reflections(Δ/σ)max = 0.001
127 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.50 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
Cl10.40101 (12)0.80466 (8)0.94032 (2)0.01990 (15)
O10.3743 (4)0.6471 (3)0.67507 (7)0.0171 (3)
O2−0.1431 (4)0.0675 (3)0.71337 (8)0.0199 (3)
O30.2057 (5)0.2458 (3)0.50473 (8)0.0265 (4)
C10.3077 (5)0.5184 (4)0.62091 (10)0.0162 (4)
C20.1464 (5)0.3212 (4)0.62998 (10)0.0160 (4)
C30.0256 (5)0.2365 (3)0.70234 (10)0.0152 (4)
C40.0441 (5)0.3071 (4)0.83526 (10)0.0159 (4)
C50.1313 (5)0.4379 (4)0.88996 (10)0.0164 (4)
C60.2909 (5)0.6400 (3)0.87083 (10)0.0150 (4)
C70.3697 (5)0.7116 (3)0.79955 (10)0.0153 (4)
C80.1182 (5)0.3730 (3)0.76188 (10)0.0138 (4)
C90.2831 (5)0.5741 (3)0.74571 (10)0.0140 (4)
C100.0936 (6)0.1938 (4)0.56551 (11)0.0201 (4)
H10.37840.56870.57270.0194*
H2−0.06740.17090.84740.0191*
H30.08400.39190.93970.0197*
H40.47850.84900.78770.0183*
H5−0.03670.06290.57230.0241*
U11U22U33U12U13U23
Cl10.0221 (3)0.0227 (3)0.0159 (3)−0.00304 (17)−0.00206 (16)−0.00573 (17)
O10.0201 (7)0.0185 (7)0.0129 (7)−0.0055 (5)0.0019 (5)−0.0007 (5)
O20.0204 (7)0.0195 (7)0.0207 (8)−0.0079 (6)0.0003 (6)−0.0018 (6)
O30.0359 (9)0.0303 (9)0.0146 (8)−0.0111 (7)0.0031 (6)−0.0054 (6)
C10.0151 (9)0.0198 (9)0.0139 (9)−0.0017 (7)−0.0004 (7)−0.0019 (7)
C20.0145 (9)0.0181 (9)0.0154 (9)−0.0010 (7)−0.0012 (7)−0.0018 (7)
C30.0108 (8)0.0168 (9)0.0181 (9)−0.0001 (7)−0.0010 (7)−0.0015 (7)
C40.0122 (9)0.0182 (9)0.0171 (9)−0.0010 (7)0.0001 (7)0.0011 (7)
C50.0158 (9)0.0179 (9)0.0151 (9)0.0001 (7)0.0010 (7)0.0007 (7)
C60.0134 (9)0.0181 (9)0.0138 (9)0.0002 (7)−0.0021 (7)−0.0042 (7)
C70.0126 (9)0.0167 (9)0.0167 (9)−0.0017 (7)−0.0004 (7)−0.0016 (7)
C80.0109 (8)0.0152 (9)0.0151 (9)−0.0000 (6)0.0005 (7)−0.0010 (7)
C90.0121 (8)0.0173 (9)0.0122 (9)−0.0005 (7)0.0004 (6)0.0007 (7)
C100.0225 (10)0.0232 (10)0.0154 (10)−0.0048 (8)−0.0013 (7)−0.0036 (8)
Cl1—C61.745 (2)C4—C81.402 (3)
O1—C11.341 (3)C5—C61.402 (3)
O1—C91.379 (3)C6—C71.377 (3)
O2—C31.231 (3)C7—C91.392 (3)
O3—C101.208 (3)C8—C91.398 (3)
C1—C21.359 (3)C1—H10.950
C2—C31.458 (3)C4—H20.950
C2—C101.480 (3)C5—H30.950
C3—C81.476 (3)C7—H40.950
C4—C51.378 (3)C10—H50.950
O1···C32.865 (3)C10···H12.5619
O1···C63.598 (3)H1···H53.4961
O2···C13.577 (3)H2···H32.3320
O2···C42.877 (3)Cl1···H2iii3.1871
O2···C102.895 (3)Cl1···H2iv3.4009
O3···C12.827 (3)Cl1···H3ii3.4824
C1···C73.578 (3)Cl1···H3xi3.0426
C1···C82.759 (3)Cl1···H3xii3.1343
C2···C92.777 (3)O1···H5iii3.3638
C4···C72.809 (3)O2···H4v2.3412
C5···C92.769 (3)O2···H4vi2.9752
C6···C82.769 (3)O3···H1ix2.8238
Cl1···Cl1i3.4483 (16)O3···H1x2.3652
Cl1···C5ii3.578 (3)O3···H5ii3.2929
O1···O2iii3.202 (3)O3···H5viii2.5304
O1···O2iv3.333 (3)C1···H5iii3.5044
O1···C2ii3.540 (3)C2···H1vii3.3800
O1···C3ii3.415 (3)C2···H5ii3.5566
O1···C8ii3.571 (3)C3···H4v3.4647
O2···O1v3.333 (3)C3···H4vi3.1692
O2···O1vi3.202 (3)C4···H2ii3.4575
O2···C2vii3.397 (3)C4···H4vi3.2692
O2···C3vii3.286 (3)C5···H2ii3.4558
O2···C7v3.204 (3)C5···H3xi3.4146
O2···C7vi3.185 (3)C6···H2iii3.3840
O2···C8vii3.393 (3)C6···H3ii3.5349
O2···C9vi3.309 (3)C7···H2iii3.2808
O3···O3viii3.430 (3)C7···H4vii3.4681
O3···O3ix3.332 (3)C8···H4vi3.3537
O3···C1ix3.278 (3)C9···H4vii3.4840
O3···C1x3.209 (3)C10···H1vii3.4338
O3···C10viii3.289 (3)C10···H1ix3.3580
C1···O3ix3.278 (3)C10···H1x3.4611
C1···O3x3.209 (3)C10···H5ii3.3751
C1···C2ii3.356 (3)C10···H5viii3.0735
C1···C3ii3.468 (3)H1···O3ix2.8238
C2···O1vii3.540 (3)H1···O3x2.3652
C2···O2ii3.397 (3)H1···C2ii3.3800
C2···C1vii3.356 (3)H1···C10ii3.4338
C3···O1vii3.415 (3)H1···C10ix3.3580
C3···O2ii3.286 (3)H1···C10x3.4611
C3···C1vii3.468 (3)H1···H1x2.9506
C3···C9vii3.481 (3)H1···H5iii3.2659
C4···C6vii3.467 (3)H1···H5ix3.5735
C4···C7vii3.476 (3)H2···Cl1v3.4009
C5···Cl1vii3.578 (3)H2···Cl1vi3.1871
C5···C6vii3.386 (4)H2···C4vii3.4575
C6···C4ii3.467 (3)H2···C5vii3.4558
C6···C5ii3.386 (4)H2···C6vi3.3840
C7···O2iii3.185 (3)H2···C7vi3.2808
C7···O2iv3.204 (3)H2···H4v2.9597
C7···C4ii3.476 (3)H2···H4vi2.9822
C7···C8ii3.479 (3)H3···Cl1vii3.4824
C8···O1vii3.571 (3)H3···Cl1xi3.0426
C8···O2ii3.393 (3)H3···Cl1xii3.1343
C8···C7vii3.479 (3)H3···C5xi3.4146
C8···C9vii3.360 (3)H3···C6vii3.5349
C9···O2iii3.309 (3)H3···H3xi2.6802
C9···C3ii3.481 (3)H4···O2iii2.9752
C9···C8ii3.360 (3)H4···O2iv2.3412
C10···O3viii3.289 (3)H4···C3iii3.1692
C10···C10viii3.575 (4)H4···C3iv3.4647
Cl1···H32.8121H4···C4iii3.2692
Cl1···H42.8064H4···C7ii3.4681
O1···H42.5238H4···C8iii3.3537
O2···H22.6135H4···C9ii3.4840
O2···H52.6106H4···H2iii2.9822
O3···H12.5045H4···H2iv2.9597
C1···H53.2854H5···O1vi3.3638
C3···H13.2928H5···O3vii3.2929
C3···H22.6818H5···O3viii2.5304
C3···H52.6956H5···C1vi3.5044
C5···H43.2981H5···C2vii3.5566
C6···H23.2536H5···C10vii3.3751
C7···H33.2895H5···C10viii3.0735
C8···H33.2766H5···H1vi3.2659
C8···H43.3034H5···H1ix3.5735
C9···H13.1896H5···H5viii2.8132
C9···H23.2637
C1—O1—C9118.62 (16)C4—C8—C9118.32 (18)
O1—C1—C2124.73 (17)O1—C9—C7115.76 (17)
C1—C2—C3120.42 (18)O1—C9—C8121.83 (18)
C1—C2—C10119.24 (17)C7—C9—C8122.41 (17)
C3—C2—C10120.34 (18)O3—C10—C2124.1 (2)
O2—C3—C2123.38 (18)O1—C1—H1117.638
O2—C3—C8122.38 (17)C2—C1—H1117.633
C2—C3—C8114.24 (17)C5—C4—H2119.644
C5—C4—C8120.70 (18)C8—C4—H2119.653
C4—C5—C6118.78 (17)C4—C5—H3120.611
Cl1—C6—C5118.56 (15)C6—C5—H3120.611
Cl1—C6—C7118.76 (15)C6—C7—H4121.444
C5—C6—C7122.66 (18)C9—C7—H4121.444
C6—C7—C9117.11 (18)O3—C10—H5117.967
C3—C8—C4121.70 (17)C2—C10—H5117.976
C3—C8—C9119.98 (17)
C1—O1—C9—C7177.96 (14)C8—C4—C5—C60.9 (3)
C1—O1—C9—C8−1.3 (3)C8—C4—C5—H3−179.1
C9—O1—C1—C21.8 (3)H2—C4—C5—C6−179.1
C9—O1—C1—H1−178.2H2—C4—C5—H30.9
O1—C1—C2—C31.1 (3)H2—C4—C8—C30.4
O1—C1—C2—C10−179.09 (14)H2—C4—C8—C9−179.8
H1—C1—C2—C3−178.9C4—C5—C6—Cl1−179.93 (14)
H1—C1—C2—C100.9C4—C5—C6—C7−1.1 (3)
C1—C2—C3—O2174.85 (16)H3—C5—C6—Cl10.1
C1—C2—C3—C8−4.3 (3)H3—C5—C6—C7178.9
C1—C2—C10—O35.1 (3)Cl1—C6—C7—C9178.98 (11)
C1—C2—C10—H5−174.9Cl1—C6—C7—H4−1.0
C3—C2—C10—O3−175.13 (16)C5—C6—C7—C90.2 (3)
C3—C2—C10—H54.9C5—C6—C7—H4−179.8
C10—C2—C3—O2−4.9 (3)C6—C7—C9—O1−178.22 (14)
C10—C2—C3—C8175.94 (14)C6—C7—C9—C81.0 (3)
O2—C3—C8—C45.4 (3)H4—C7—C9—O11.8
O2—C3—C8—C9−174.38 (15)H4—C7—C9—C8−179.0
C2—C3—C8—C4−175.44 (14)C3—C8—C9—O1−2.2 (3)
C2—C3—C8—C94.8 (3)C3—C8—C9—C7178.65 (14)
C5—C4—C8—C3−179.64 (15)C4—C8—C9—O1178.01 (14)
C5—C4—C8—C90.1 (3)C4—C8—C9—C7−1.1 (3)
D—H···AD—HH···AD···AD—H···A
C7—H4···O2iv0.952.343.204 (3)151 (1)
C1—H1···O3x0.952.373.209 (3)148 (1)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C7—H4⋯O2i 0.952.343.204 (3)151 (1)
C1—H1⋯O3ii 0.952.373.209 (3)148 (1)

Symmetry codes: (i) ; (ii) .

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