Literature DB >> 25309300

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

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H5BrO3, a brominated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. = 0.0631 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.215 (3) Å] being for the formyl O atom. In the crystal, mol-ecules are linked into tapes through C-H⋯O hydrogen bonds and these tapes are assembled by stacking inter-actions [centroid-centroid distance between the pyran rings = 3.858 (3) Å] to form supra-molecular layers that stack along the c axis.

Entities:  

Keywords:  C—H⋯O hydrogen bonding; chromone; crystal structure; stacking inter­action

Year:  2014        PMID： 25309300      PMCID： PMC4186120          DOI： 10.1107/S1600536814018108

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


Related literature

For related structures, see: 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

C10H5BrO3 M = 253.05 Monoclinic, a = 3.8580 (18) Å b = 6.054 (4) Å c = 37.268 (13) Å β = 90.39 (4)° V = 870.4 (8) Å3 Z = 4 Mo Kα radiation μ = 4.71 mm−1 T = 100 K 0.45 × 0.20 × 0.10 mm

Data collection

Rigaku AFC-7R diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.339, T max = 0.624 4817 measured reflections 1980 independent reflections 1710 reflections with F 2 > 2σ(F 2) R int = 0.024 3 standard reflections every 150 reflections intensity decay: 4.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.109 S = 1.07 1980 reflections 127 parameters H-atom parameters constrained Δρmax = 1.26 e Å−3 Δρmin = −1.73 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/S1600536814018108/tk5337sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018108/tk5337Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814018108/tk5337Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814018108/tk5337fig1.tif The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius. Click here for additional data file. . DOI: 10.1107/S1600536814018108/tk5337fig2.tif A packing view of the title compound. C—H⋯O hydrogen bonds are represented by dashed lines. Click here for additional data file. H a H b . DOI: 10.1107/S1600536814018108/tk5337fig3.tif Sphere models of the crystal structures of 6,8-di­bromo-4-oxo-4H-chromene-3-carbaldehyde (top, Ishikawa, 2014a), 6-bromo-4-oxo-4H-chromene-3-carbaldehyde (middle, Ishikawa, 2014b), and the title compound (bottom, this work). CCDC reference: 1018275 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H5BrO3F(000) = 496.00
Mr = 253.05Dx = 1.931 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 3.8580 (18) Åθ = 15.3–17.5°
b = 6.054 (4) ŵ = 4.71 mm−1
c = 37.268 (13) ÅT = 100 K
β = 90.39 (4)°Plate, colourless
V = 870.4 (8) Å30.45 × 0.20 × 0.10 mm
Z = 4
Rigaku AFC-7R diffractometerRint = 0.024
ω scansθmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)h = −5→2
Tmin = 0.339, Tmax = 0.624k = −7→7
4817 measured reflectionsl = −48→48
1980 independent reflections3 standard reflections every 150 reflections
1710 reflections with F2 > 2σ(F2) intensity decay: 4.8%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0756P)2 + 0.989P] where P = (Fo2 + 2Fc2)/3
1980 reflections(Δ/σ)max = 0.002
127 parametersΔρmax = 1.26 e Å−3
0 restraintsΔρmin = −1.73 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
Br10.08234 (8)0.06978 (6)0.719199 (7)0.01987 (15)
O10.1286 (6)0.3047 (4)0.58604 (6)0.0198 (5)
O20.6540 (7)0.8813 (4)0.60418 (6)0.0253 (6)
O30.2989 (8)0.7487 (5)0.50270 (6)0.0321 (6)
C10.1969 (9)0.4490 (6)0.55957 (8)0.0199 (7)
C20.3614 (9)0.6437 (6)0.56382 (8)0.0190 (7)
C30.4862 (8)0.7122 (6)0.59908 (8)0.0181 (6)
C40.4730 (9)0.6080 (6)0.66421 (8)0.0173 (6)
C50.3830 (9)0.4628 (6)0.69123 (8)0.0187 (7)
C60.2140 (8)0.2670 (6)0.68222 (8)0.0167 (6)
C70.1322 (8)0.2111 (6)0.64716 (8)0.0170 (6)
C80.3930 (9)0.5598 (5)0.62828 (8)0.0169 (7)
C90.2221 (8)0.3622 (6)0.62059 (8)0.0164 (6)
C100.4165 (9)0.7874 (7)0.53244 (9)0.0256 (8)
H10.12330.41060.53600.0238*
H20.59000.74150.67000.0207*
H30.43570.49610.71560.0224*
H40.01970.07590.64150.0203*
H50.55120.91740.53560.0307*
U11U22U33U12U13U23
Br10.0190 (3)0.0305 (3)0.01010 (19)−0.00138 (11)0.00019 (12)0.00367 (11)
O10.0260 (12)0.0252 (12)0.0083 (10)−0.0074 (10)−0.0036 (9)−0.0010 (9)
O20.0336 (14)0.0259 (12)0.0162 (11)−0.0107 (11)−0.0033 (10)−0.0010 (10)
O30.0437 (16)0.0392 (15)0.0133 (12)−0.0131 (12)−0.0067 (11)0.0046 (11)
C10.0209 (16)0.0291 (18)0.0095 (14)−0.0034 (13)−0.0018 (12)−0.0010 (12)
C20.0214 (16)0.0261 (16)0.0096 (13)−0.0028 (13)−0.0008 (12)0.0006 (12)
C30.0197 (15)0.0240 (15)0.0107 (14)−0.0011 (12)0.0011 (11)−0.0015 (12)
C40.0175 (15)0.0245 (16)0.0098 (14)−0.0003 (12)−0.0021 (11)−0.0049 (12)
C50.0192 (16)0.0268 (17)0.0099 (14)−0.0008 (12)−0.0015 (12)−0.0030 (12)
C60.0149 (14)0.0260 (16)0.0091 (13)0.0001 (12)−0.0003 (10)0.0001 (12)
C70.0154 (14)0.0226 (15)0.0128 (14)−0.0035 (12)−0.0017 (11)−0.0022 (12)
C80.0179 (15)0.0231 (16)0.0095 (14)−0.0023 (12)−0.0013 (12)−0.0014 (11)
C90.0175 (15)0.0247 (15)0.0070 (13)−0.0010 (12)−0.0022 (11)−0.0043 (12)
C100.0299 (19)0.0299 (17)0.0171 (16)−0.0078 (15)−0.0006 (14)0.0021 (14)
Br1—C61.895 (4)C4—C81.403 (5)
O1—C11.345 (4)C5—C61.393 (5)
O1—C91.379 (4)C6—C71.384 (5)
O2—C31.226 (4)C7—C91.394 (5)
O3—C101.217 (5)C8—C91.395 (5)
C1—C21.348 (5)C1—H10.950
C2—C31.457 (5)C4—H20.950
C2—C101.474 (5)C5—H30.950
C3—C81.473 (5)C7—H40.950
C4—C51.382 (5)C10—H50.950
O1···C32.866 (5)C10···H12.5501
O2···C13.561 (5)H1···H53.4843
O2···C42.873 (4)H2···H32.3357
O2···C102.877 (5)Br1···H2i3.2968
O3···C12.820 (4)Br1···H2ii3.3454
C1···C73.578 (5)Br1···H3iii3.5917
C1···C82.748 (5)Br1···H3x3.1886
C2···C92.772 (5)Br1···H3xi3.0827
C4···C72.810 (5)O1···H5ii3.4250
C5···C92.769 (5)O2···H4iv3.0581
C6···C82.771 (5)O2···H4v2.2984
O1···O2i3.224 (4)O3···H1ix2.3733
O1···O2ii3.334 (4)O3···H1vii2.8324
O1···C3iii3.533 (5)O3···H5iii3.3041
O2···O1iv3.334 (4)O3···H5viii2.5428
O2···O1v3.224 (4)C2···H1vi3.4277
O2···C2vi3.440 (5)C3···H4iv3.2588
O2···C3vi3.376 (5)C3···H4v3.3965
O2···C7iv3.263 (4)C4···H2iii3.5093
O2···C7v3.149 (4)C4···H4iv3.4320
O2···C8vi3.562 (5)C5···H2iii3.5776
O2···C9iv3.412 (5)C6···H2ii3.5270
O3···O3vii3.394 (5)C6···H3iii3.5409
O3···O3viii3.422 (5)C7···H2ii3.4509
O3···C1ix3.228 (5)C7···H4vi3.5285
O3···C1vii3.265 (5)C8···H4iv3.4764
O3···C10iii3.595 (5)C10···H1vi3.5572
O3···C10viii3.290 (5)C10···H1ix3.4940
C1···O3ix3.228 (5)C10···H1vii3.3402
C1···O3vii3.265 (5)C10···H5iii3.4327
C1···C2iii3.437 (5)C10···H5viii3.1048
C1···C3iii3.504 (5)H1···O3ix2.3733
C2···O2iii3.440 (5)H1···O3vii2.8324
C2···C1vi3.437 (5)H1···C2iii3.4277
C3···O1vi3.533 (5)H1···C10iii3.5572
C3···O2iii3.376 (5)H1···C10ix3.4940
C3···C1vi3.504 (5)H1···C10vii3.3402
C4···C6vi3.586 (5)H1···H1ix3.0401
C4···C7vi3.559 (5)H1···H5ii3.4115
C5···C6vi3.437 (5)H1···H5vii3.5617
C6···C4iii3.586 (5)H2···Br1iv3.3454
C6···C5iii3.437 (5)H2···Br1v3.2968
C7···O2i3.149 (4)H2···C4vi3.5093
C7···O2ii3.263 (4)H2···C5vi3.5776
C7···C4iii3.559 (5)H2···C6iv3.5270
C8···O2iii3.562 (5)H2···C7iv3.4509
C8···C9vi3.429 (5)H2···H4iv3.1684
C9···O2ii3.412 (5)H2···H4v2.8291
C9···C8iii3.429 (5)H3···Br1vi3.5917
C10···O3vi3.595 (5)H3···Br1xii3.1886
C10···O3viii3.290 (5)H3···Br1xiii3.0827
C10···C10viii3.593 (6)H3···C6vi3.5409
Br1···H32.9226H4···O2i2.2984
Br1···H42.9055H4···O2ii3.0581
O1···H42.5249H4···C3i3.3965
O2···H22.6093H4···C3ii3.2588
O2···H52.5934H4···C4ii3.4320
O3···H12.4901H4···C7iii3.5285
C1···H53.2749H4···C8ii3.4764
C3···H13.2825H4···H2i2.8291
C3···H22.6775H4···H2ii3.1684
C3···H52.6858H5···O1iv3.4250
C5···H43.2949H5···O3vi3.3041
C6···H23.2513H5···O3viii2.5428
C7···H33.2879H5···C10vi3.4327
C8···H33.2793H5···C10viii3.1048
C8···H43.3027H5···H1iv3.4115
C9···H13.1864H5···H1vii3.5617
C9···H23.2628H5···H5viii2.8597
C1—O1—C9118.0 (3)C4—C8—C9118.4 (3)
O1—C1—C2125.2 (3)O1—C9—C7115.7 (3)
C1—C2—C3120.5 (3)O1—C9—C8121.9 (3)
C1—C2—C10119.6 (3)C7—C9—C8122.4 (3)
C3—C2—C10120.0 (3)O3—C10—C2123.6 (4)
O2—C3—C2123.3 (3)O1—C1—H1117.410
O2—C3—C8122.7 (3)C2—C1—H1117.401
C2—C3—C8114.0 (3)C5—C4—H2119.709
C5—C4—C8120.6 (3)C8—C4—H2119.732
C4—C5—C6119.0 (3)C4—C5—H3120.507
Br1—C6—C5119.2 (3)C6—C5—H3120.495
Br1—C6—C7118.2 (3)C6—C7—H4121.481
C5—C6—C7122.6 (3)C9—C7—H4121.508
C6—C7—C9117.0 (3)O3—C10—H5118.165
C3—C8—C4121.4 (3)C2—C10—H5118.205
C3—C8—C9120.2 (3)
C1—O1—C9—C7177.4 (3)C8—C4—C5—C60.5 (5)
C1—O1—C9—C8−2.2 (4)C8—C4—C5—H3−179.5
C9—O1—C1—C22.5 (5)H2—C4—C5—C6−179.5
C9—O1—C1—H1−177.5H2—C4—C5—H30.5
O1—C1—C2—C30.9 (5)H2—C4—C8—C3−0.0
O1—C1—C2—C10−179.4 (3)H2—C4—C8—C9179.8
H1—C1—C2—C3−179.1C4—C5—C6—Br1−178.8 (3)
H1—C1—C2—C100.6C4—C5—C6—C70.1 (5)
C1—C2—C3—O2175.8 (3)H3—C5—C6—Br11.1
C1—C2—C3—C8−4.2 (5)H3—C5—C6—C7−179.9
C1—C2—C10—O35.6 (5)Br1—C6—C7—C9178.02 (18)
C1—C2—C10—H5−174.4Br1—C6—C7—H4−2.0
C3—C2—C10—O3−174.7 (3)C5—C6—C7—C9−0.9 (5)
C3—C2—C10—H55.3C5—C6—C7—H4179.1
C10—C2—C3—O2−3.9 (5)C6—C7—C9—O1−178.3 (3)
C10—C2—C3—C8176.1 (3)C6—C7—C9—C81.2 (5)
O2—C3—C8—C44.2 (5)H4—C7—C9—O11.7
O2—C3—C8—C9−175.6 (3)H4—C7—C9—C8−178.8
C2—C3—C8—C4−175.8 (3)C3—C8—C9—O1−1.4 (5)
C2—C3—C8—C94.4 (4)C3—C8—C9—C7179.2 (3)
C5—C4—C8—C3180.0 (3)C4—C8—C9—O1178.8 (3)
C5—C4—C8—C9−0.2 (5)C4—C8—C9—C7−0.7 (5)
D—H···AD—HH···AD···AD—H···A
C7v—H4v···O20.952.303.149 (4)149 (1)
C1ix—H1ix···O30.952.373.228 (5)149 (1)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C7i—H4i⋯O20.952.303.149 (4)149 (1)
C1ii—H1ii⋯O30.952.373.228 (5)149 (1)

Symmetry codes: (i) ; (ii) .

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1.  A short history of SHELX.

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4.  Halogen bonds in biological molecules.

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

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7.  6,8-Di-bromo-4-oxo-4H-chromene-3-carbaldehyde.

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8.  Halogen bonds in some dihalogenated phenols: applications to crystal engineering.

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9.  Type II halogen···halogen contacts are halogen bonds.

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  2 in total

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