Literature DB >> 26396803

Crystal structure of 8-bromo-4-oxo-4H-chromene-3-carbaldehyde.

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H5BrO3, a brominated 3-formyl-chromone, all atoms are essentially coplanar (r.m.s. = 0.0104 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.028 (5) Å] being for one of the benzene C atoms. In the crystal, mol-ecules are linked through C-H⋯O hydrogen bonds, which are further assembled by face-to-face π-π stacking inter-actions [centroid-centroid distance between the pyran rings = 3.854 (4) Å]. Shorter contacts than the sum of van der Waals radii are observed between the Br and formyl O atoms [Br⋯O = 3.046 (4) Å, C-Br⋯O = 175.23 (18)° and Br⋯O-C = 132.6 (3)°], features that do indicate halogen bonding.

Entities:  

Keywords:  chromone; crystal structure; halogen bonding; hydrogen bonding; π–π stacking

Year:  2015        PMID： 26396803      PMCID： PMC4571403          DOI： 10.1107/S2056989015013250

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


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 ▸); Persch et al. (2015 ▸); Metrangolo & Resnati (2014 ▸); Mukherjee & Desiraju (2014 ▸).

Experimental

Crystal data

C10H5BrO3 M = 253.05 Monoclinic, a = 27.908 (14) Å b = 3.854 (3) Å c = 19.145 (10) Å β = 123.75 (4)° V = 1712.1 (18) Å3 Z = 8 Mo Kα radiation μ = 4.79 mm−1 T = 100 K 0.37 × 0.10 × 0.07 mm

Data collection

Rigaku AFC-7R diffractometer Absorption correction: ψ scan (North et al., 1968 ▸) T min = 0.546, T max = 0.715 2556 measured reflections 1940 independent reflections 1280 reflections with F 2 > 2.0σ(F 2) R int = 0.020 3 standard reflections every 150 reflections intensity decay: −0.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.102 S = 1.02 1940 reflections 127 parameters H-atom parameters constrained Δρmax = 1.40 e Å−3 Δρmin = −1.27 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: SIR92 (Altomare et al., 1994 ▸); 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/S2056989015013250/zl2634sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013250/zl2634Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015013250/zl2634Isup3.cml Click here for additional data file. a H a b H b c . DOI: 10.1107/S2056989015013250/zl2634fig1.tif Sphere models of the crystal structures of (a) 6-bromo-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa, 2014a), (b) 7-bromo-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa, 2014b) and (c) the title compound (this work). Click here for additional data file. . DOI: 10.1107/S2056989015013250/zl2634fig2.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/S2056989015013250/zl2634fig3.tif A packing view of the title compound. C—H⋯O hydrogen bonds and Br⋯O halogen bonds are represented by dashed lines. CCDC reference: 1412014 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H5BrO3F(000) = 992.00
Mr = 253.05Dx = 1.963 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 27.908 (14) Åθ = 15.0–17.3°
b = 3.854 (3) ŵ = 4.79 mm−1
c = 19.145 (10) ÅT = 100 K
β = 123.75 (4)°Plate, yellow
V = 1712.1 (18) Å30.37 × 0.10 × 0.07 mm
Z = 8
Rigaku AFC-7R diffractometerRint = 0.020
ω scansθmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)h = −20→36
Tmin = 0.546, Tmax = 0.715k = −4→2
2556 measured reflectionsl = −24→20
1940 independent reflections3 standard reflections every 150 reflections
1280 reflections with F2 > 2.0σ(F2) intensity decay: −0.8%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0578P)2 + 0.244P] where P = (Fo2 + 2Fc2)/3
1940 reflections(Δ/σ)max = 0.004
127 parametersΔρmax = 1.40 e Å−3
0 restraintsΔρmin = −1.27 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
Br11.005108 (15)−0.24742 (12)0.90755 (2)0.01865 (14)
O10.93556 (11)0.0942 (8)0.73881 (17)0.0180 (6)
O20.76802 (12)0.4314 (9)0.60186 (18)0.0261 (8)
O30.86856 (12)0.5554 (9)0.50725 (18)0.0277 (8)
C10.91204 (17)0.2414 (12)0.6633 (3)0.0188 (8)
C20.85673 (18)0.3611 (12)0.6140 (3)0.0188 (9)
C30.81785 (19)0.3273 (11)0.6431 (3)0.0199 (10)
C40.81361 (17)0.1171 (13)0.7636 (3)0.0220 (10)
C50.83890 (17)−0.0311 (12)0.8415 (3)0.0201 (10)
C60.89618 (18)−0.1386 (13)0.8849 (3)0.0212 (10)
C70.92747 (16)−0.0988 (12)0.8491 (3)0.0161 (9)
C80.84441 (18)0.1649 (11)0.7261 (3)0.0171 (10)
C90.90209 (16)0.0568 (11)0.7709 (3)0.0165 (9)
C100.83814 (19)0.5220 (12)0.5332 (3)0.0216 (10)
H10.93570.26460.64220.0226*
H20.77450.18910.73450.0264*
H30.8174−0.06060.86590.0241*
H40.9138−0.23920.93910.0254*
H50.79970.60510.49910.0260*
U11U22U33U12U13U23
Br10.0141 (2)0.0192 (3)0.0204 (2)0.0019 (2)0.00822 (16)0.0016 (2)
O10.0123 (13)0.0238 (16)0.0188 (14)0.0028 (13)0.0093 (12)0.0037 (14)
O20.0140 (15)0.034 (2)0.0266 (17)0.0055 (15)0.0090 (13)0.0042 (16)
O30.0218 (16)0.039 (3)0.0243 (16)0.0025 (16)0.0139 (14)0.0031 (16)
C10.0189 (19)0.022 (3)0.0196 (18)0.002 (3)0.0131 (16)0.000 (3)
C20.019 (2)0.020 (3)0.017 (2)0.0013 (18)0.0104 (18)−0.0010 (17)
C30.021 (2)0.017 (3)0.022 (2)−0.0013 (16)0.0120 (18)−0.0011 (16)
C40.0107 (19)0.027 (3)0.027 (3)−0.0006 (19)0.0094 (18)−0.003 (2)
C50.018 (2)0.024 (3)0.023 (2)−0.0074 (19)0.0137 (18)−0.0038 (19)
C60.020 (2)0.024 (3)0.018 (2)−0.0038 (19)0.0097 (18)−0.0027 (18)
C70.0126 (19)0.0132 (19)0.022 (2)−0.0012 (18)0.0095 (17)0.0004 (18)
C80.0148 (19)0.015 (3)0.018 (2)−0.0004 (16)0.0071 (17)−0.0004 (15)
C90.0137 (19)0.020 (3)0.018 (2)−0.0004 (18)0.0102 (17)−0.0031 (18)
C100.024 (3)0.021 (3)0.020 (2)0.0023 (19)0.0115 (18)0.0006 (19)
Br1—C71.892 (4)C4—C81.405 (9)
O1—C11.337 (5)C5—C61.393 (6)
O1—C91.381 (7)C6—C71.387 (9)
O2—C31.224 (6)C7—C91.387 (6)
O3—C101.205 (8)C8—C91.402 (6)
C1—C21.367 (6)C1—H10.950
C2—C31.475 (9)C4—H20.950
C2—C101.469 (7)C5—H30.950
C3—C81.469 (7)C6—H40.950
C4—C51.370 (7)C10—H50.950
Br1···O12.995 (4)Br1···H1i2.9874
O1···C32.875 (6)Br1···H1ii3.0464
O2···C13.581 (7)Br1···H4xii3.2048
O2···C42.881 (6)Br1···H4xiii3.1419
O2···C102.922 (8)O1···H1ii3.0722
O3···C12.799 (6)O2···H3xiv2.7748
C1···C73.585 (8)O2···H5v2.7432
C1···C82.760 (9)O2···H5vi2.5376
C2···C92.787 (7)O3···H1iv3.5037
C4···C72.773 (6)O3···H3viii2.9507
C5···C92.775 (9)O3···H3ix2.9772
C6···C82.796 (7)O3···H4viii2.5712
Br1···O3i3.046 (4)O3···H4ix3.4743
O1···O1ii3.378 (6)C2···H5iii3.4598
O1···C1iii3.503 (6)C3···H5v3.3207
O1···C2iii3.562 (6)C4···H2xv2.9781
O2···C8iv3.544 (6)C4···H2xiv3.3174
O2···C10v3.163 (5)C4···H3xiv3.3139
O2···C10vi3.375 (5)C5···H2iii3.5171
O3···Br1vii3.046 (4)C5···H2xv2.8601
O3···C5viii3.452 (6)C5···H4iv3.5832
O3···C5ix3.347 (6)C6···H4iv3.5732
O3···C6viii3.266 (8)C10···H3viii3.4200
C1···O1iv3.503 (6)C10···H3ix3.5839
C1···C10iii3.527 (6)H1···Br1ii3.0464
C2···O1iv3.562 (6)H1···Br1vii2.9874
C2···C10iii3.497 (7)H1···O1ii3.0722
C3···C8iv3.491 (7)H1···O3iii3.5037
C4···C5iv3.511 (7)H1···H4viii3.5860
C5···O3x3.452 (6)H2···C4xv3.3174
C5···O3xi3.347 (6)H2···C4xiv2.9781
C5···C4iii3.511 (7)H2···C5iv3.5171
C6···O3x3.266 (8)H2···C5xiv2.8601
C7···C8iii3.592 (6)H2···H2xv2.6156
C7···C9iii3.486 (7)H2···H2xiv2.6156
C8···O2iii3.544 (6)H2···H3iv3.5746
C8···C3iii3.491 (7)H2···H3xiv2.3921
C8···C7iv3.592 (6)H3···O2xv2.7748
C9···C7iv3.486 (7)H3···O3x2.9507
C10···O2v3.163 (5)H3···O3xi2.9772
C10···O2vi3.375 (5)H3···C4xv3.3139
C10···C1iv3.527 (6)H3···C10x3.4200
C10···C2iv3.497 (7)H3···C10xi3.5839
Br1···H42.9274H3···H2iii3.5746
O2···H22.6153H3···H2xv2.3921
O2···H52.6505H3···H5x3.5442
O3···H12.4620H3···H5xi3.3525
C1···H53.2749H4···Br1xii3.2048
C3···H13.3068H4···Br1xiii3.1419
C3···H22.6753H4···O3x2.5712
C3···H52.7288H4···O3xi3.4743
C4···H43.2489H4···C5iii3.5832
C6···H23.2487H4···C6iii3.5732
C7···H33.2654H4···H1x3.5860
C8···H33.2750H5···O2v2.7432
C9···H13.1865H5···O2vi2.5376
C9···H23.2660H5···C2iv3.4598
C9···H43.2581H5···C3v3.3207
C10···H12.5371H5···H3viii3.5442
H1···H53.4755H5···H3ix3.3525
H2···H32.3112H5···H5vi3.0057
H3···H42.3430
C1—O1—C9118.5 (4)C4—C8—C9118.0 (4)
O1—C1—C2125.2 (6)O1—C9—C7117.3 (4)
C1—C2—C3119.7 (5)O1—C9—C8121.9 (4)
C1—C2—C10118.2 (6)C7—C9—C8120.8 (5)
C3—C2—C10122.1 (4)O3—C10—C2124.2 (4)
O2—C3—C2122.5 (5)O1—C1—H1117.386
O2—C3—C8123.2 (6)C2—C1—H1117.377
C2—C3—C8114.3 (4)C5—C4—H2119.373
C5—C4—C8121.3 (4)C8—C4—H2119.362
C4—C5—C6120.0 (6)C4—C5—H3120.002
C5—C6—C7120.1 (5)C6—C5—H3120.002
Br1—C7—C6120.2 (3)C5—C6—H4119.976
Br1—C7—C9120.0 (4)C7—C6—H4119.964
C6—C7—C9119.8 (4)O3—C10—H5117.902
C3—C8—C4121.6 (4)C2—C10—H5117.903
C3—C8—C9120.4 (6)
C1—O1—C9—C7179.6 (4)C8—C4—C5—C6−0.2 (7)
C1—O1—C9—C80.7 (6)C8—C4—C5—H3179.8
C9—O1—C1—C20.1 (6)H2—C4—C5—C6179.8
C9—O1—C1—H1−179.9H2—C4—C5—H3−0.2
O1—C1—C2—C3−0.9 (7)H2—C4—C8—C30.7
O1—C1—C2—C10178.9 (4)H2—C4—C8—C9179.8
H1—C1—C2—C3179.1C4—C5—C6—C7−0.6 (7)
H1—C1—C2—C10−1.1C4—C5—C6—H4179.4
C1—C2—C3—O2179.6 (4)H3—C5—C6—C7179.4
C1—C2—C3—C80.7 (6)H3—C5—C6—H4−0.6
C1—C2—C10—O30.1 (7)C5—C6—C7—Br1−179.6 (4)
C1—C2—C10—H5−179.9C5—C6—C7—C91.8 (7)
C3—C2—C10—O3179.8 (4)H4—C6—C7—Br10.4
C3—C2—C10—H5−0.2H4—C6—C7—C9−178.2
C10—C2—C3—O2−0.1 (7)Br1—C7—C9—O10.4 (6)
C10—C2—C3—C8−179.0 (4)Br1—C7—C9—C8179.2 (3)
O2—C3—C8—C40.3 (6)C6—C7—C9—O1179.1 (4)
O2—C3—C8—C9−178.8 (4)C6—C7—C9—C8−2.1 (7)
C2—C3—C8—C4179.1 (4)C3—C8—C9—O1−0.8 (6)
C2—C3—C8—C90.1 (6)C3—C8—C9—C7−179.6 (4)
C5—C4—C8—C3−179.3 (4)C4—C8—C9—O1−179.9 (4)
C5—C4—C8—C9−0.2 (7)C4—C8—C9—C71.3 (6)
D—H···AD—HH···AD···AD—H···A
C10—H5···O2vi0.952.543.375 (5)147 (1)
C7—Br1···O3i1.89 (1)3.05 (1)4.934 (6)175 (1)
C10—O3···Br1vii1.21 (1)3.05 (1)3.962 (6)133 (1)
Table 1

Hydrogen-bond geometry (, )

DHA DHHA D A DHA
C10H5O2i 0.952.543.375(5)147(1)
C7Br1O3ii 1.89(1)3.05(1)4.934(6)175(1)
C10O3Br1iii 1.21(1)3.05(1)3.962(6)133(1)

Symmetry codes: (i) ; (ii) ; (iii) .

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