Literature DB >> 24860346

6,8-Di-iodo-4-oxo-4H-chromene-3-carbalde-hyde.

Yoshinobu Ishikawa1.   

Abstract

The title compound, C10H4I2O3, is an iodinated 3-formyl-chromone derivative, and the atoms are essentially coplanar [r.m.s. deviation = 0.049 Å, largest deviation from the least-squares plane = 0.111 (9) Å for the CH(=O) C atom]. In the crystal, mol-ecules are linked into a three-dimensional network through halogen bonds [I⋯O = 3.352 (5) and 3.405 (7) Å, C-I⋯O = 144.2 (3) and 154.5 (3)°, and C=O⋯I = 134.9 (6) and 146.0 (6)°], and π-π stacking inter-actions [centroid-centroid distance = 3.527 (6) Å].

Entities:  

Year:  2014        PMID： 24860346      PMCID： PMC4011213          DOI： 10.1107/S1600536814006904

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


Related literature

For the preparation of the precursor of the title compound, see: Khansole et al. (2008 ▶). 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 ▶).

Experimental

Crystal data

C10H4I2O3 M = 425.95 Triclinic, a = 7.290 (3) Å b = 8.779 (5) Å c = 9.767 (4) Å α = 63.82 (3)° β = 75.44 (3)° γ = 68.05 (4)° V = 517.5 (5) Å3 Z = 2 Mo Kα radiation μ = 6.06 mm−1 T = 100 K 0.48 × 0.30 × 0.25 mm

Data collection

Rigaku AFC-7R diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.152, T max = 0.220 2933 measured reflections 2383 independent reflections 2361 reflections with F 2 > 2σ(F 2) R int = 0.026 3 standard reflections every 150 reflections intensity decay: −1.1%

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.147 S = 1.23 2383 reflections 137 parameters H-atom parameters constrained Δρmax = 3.56 e Å−3 Δρmin = −3.01 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/S1600536814006904/zl2583sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006904/zl2583Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814006904/zl2583Isup3.cml CCDC reference: 994113 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H4I2O3Z = 2
Mr = 425.95F(000) = 388.00
Triclinic, P1Dx = 2.733 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 7.290 (3) ÅCell parameters from 25 reflections
b = 8.779 (5) Åθ = 15.2–17.1°
c = 9.767 (4) ŵ = 6.06 mm−1
α = 63.82 (3)°T = 100 K
β = 75.44 (3)°Block, yellow
γ = 68.05 (4)°0.48 × 0.30 × 0.25 mm
V = 517.5 (5) Å3
Rigaku AFC-7R diffractometerRint = 0.026
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)h = −5→9
Tmin = 0.152, Tmax = 0.220k = −10→11
2933 measured reflectionsl = −12→12
2383 independent reflections3 standard reflections every 150 reflections
2361 reflections with F2 > 2σ(F2) intensity decay: −1.1%
Refinement on F2Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.147w = 1/[σ2(Fo2) + (0.0884P)2 + 4.3985P] where P = (Fo2 + 2Fc2)/3
S = 1.23(Δ/σ)max = 0.001
2383 reflectionsΔρmax = 3.56 e Å−3
137 parametersΔρmin = −3.01 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (3)
Secondary atom site location: difference Fourier map
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
I10.32790 (6)0.83369 (5)0.74688 (5)0.0152 (3)
I20.74091 (6)0.06022 (5)0.85492 (5)0.0179 (3)
O10.9121 (7)0.2469 (6)0.5147 (6)0.0131 (9)
O20.8156 (8)0.7689 (7)0.2159 (6)0.0180 (10)
O31.2172 (8)0.3795 (8)0.0749 (6)0.0197 (10)
C11.0076 (10)0.2949 (10)0.3730 (8)0.0163 (13)
C20.9844 (9)0.4629 (10)0.2687 (8)0.0129 (12)
C30.8432 (9)0.6141 (9)0.3051 (7)0.0109 (12)
C40.6053 (10)0.6899 (9)0.5166 (8)0.0125 (12)
C50.5157 (10)0.6387 (9)0.6645 (8)0.0135 (12)
C60.5540 (10)0.4571 (10)0.7630 (8)0.0146 (12)
C70.6876 (10)0.3271 (9)0.7098 (7)0.0128 (12)
C80.7425 (9)0.5587 (9)0.4625 (7)0.0118 (12)
C90.7809 (9)0.3800 (8)0.5608 (7)0.0104 (11)
C101.1073 (10)0.4944 (9)0.1196 (8)0.0128 (12)
H11.10020.20200.34350.0196*
H20.57560.81240.45090.0150*
H30.48960.42340.86460.0176*
H41.09950.61440.05360.0153*
U11U22U33U12U13U23
I10.0159 (3)0.0127 (3)0.0163 (3)−0.00142 (18)0.00485 (17)−0.0107 (2)
I20.0180 (3)0.0106 (3)0.0169 (3)−0.00243 (19)0.00704 (18)−0.0045 (2)
O10.014 (2)0.010 (2)0.013 (2)−0.0006 (17)0.0030 (17)−0.0082 (17)
O20.019 (3)0.016 (3)0.012 (3)−0.0030 (19)0.0043 (18)−0.0046 (19)
O30.017 (3)0.026 (3)0.015 (3)−0.003 (2)0.0040 (18)−0.012 (2)
C10.014 (3)0.021 (4)0.016 (3)−0.004 (3)0.001 (3)−0.012 (3)
C20.007 (3)0.023 (4)0.015 (3)−0.006 (3)0.004 (3)−0.015 (3)
C30.008 (3)0.016 (3)0.010 (3)−0.003 (3)0.003 (2)−0.010 (3)
C40.015 (3)0.009 (3)0.013 (3)−0.002 (3)−0.005 (3)−0.004 (3)
C50.011 (3)0.016 (3)0.018 (3)−0.005 (3)0.002 (3)−0.011 (3)
C60.014 (3)0.026 (4)0.010 (3)−0.010 (3)0.006 (2)−0.012 (3)
C70.014 (3)0.016 (3)0.011 (3)−0.006 (3)0.002 (3)−0.007 (3)
C80.013 (3)0.015 (3)0.009 (3)−0.007 (3)0.003 (3)−0.006 (3)
C90.013 (3)0.010 (3)0.011 (3)−0.003 (3)0.002 (3)−0.008 (3)
C100.012 (3)0.015 (3)0.010 (3)−0.001 (3)0.001 (3)−0.008 (3)
I1—C52.088 (8)C4—C51.373 (9)
I2—C72.077 (7)C4—C81.420 (10)
O1—C11.340 (8)C5—C61.412 (9)
O1—C91.377 (9)C6—C71.399 (11)
O2—C31.219 (8)C7—C91.392 (9)
O3—C101.208 (10)C8—C91.392 (8)
C1—C21.348 (9)C1—H10.950
C2—C31.470 (10)C4—H20.950
C2—C101.474 (9)C6—H30.950
C3—C81.476 (9)C10—H40.950
I2···O13.150 (5)C9···C5v3.539 (13)
O1···C32.884 (8)C10···O3vii2.980 (10)
O2···C13.566 (9)C10···C5ii3.421 (11)
O2···C42.862 (8)C10···C6ii3.199 (13)
O2···C102.895 (9)C10···C7ii3.574 (14)
O3···C12.840 (8)C10···C10vii3.072 (13)
C1···C73.579 (10)I1···H23.0418
C1···C82.730 (11)I1···H33.0886
C2···C92.778 (9)I2···H33.0562
C4···C72.811 (9)O2···H22.5939
C5···C92.772 (10)O2···H42.6052
C6···C82.806 (9)O3···H12.5096
I1···O2i3.405 (7)C1···H43.2682
I1···O3ii3.594 (6)C3···H13.2906
I2···O2iii3.352 (5)C3···H22.6671
I2···O3iv3.514 (7)C3···H42.6866
O1···C3ii3.587 (12)C4···H33.2790
O1···C5v3.557 (10)C6···H23.2839
O2···I1i3.405 (7)C9···H13.1762
O2···I2vi3.352 (5)C9···H23.2812
O2···C7ii3.585 (10)C9···H33.2682
O2···C9ii3.599 (10)C10···H12.5423
O3···I1ii3.594 (6)H1···H43.4744
O3···I2iv3.514 (7)I1···H2i3.0877
O3···O3vii3.353 (8)I1···H4ix3.2019
O3···C2vii3.493 (10)I2···H1iv3.3483
O3···C5ii3.492 (12)O1···H1iv3.5832
O3···C6viii3.381 (8)O3···H3viii2.4768
O3···C6ii3.531 (13)O3···H3ii3.4952
O3···C10vii2.980 (10)O3···H4vii2.8657
C1···C4ii3.329 (13)C1···H2ii3.4833
C1···C8ii3.548 (14)C3···H3v3.4417
C2···O3vii3.493 (10)C4···H1ii3.3938
C2···C4ii3.580 (11)C5···H1ii3.5387
C2···C5ii3.571 (11)C6···H4ii3.1756
C2···C8ii3.577 (12)C7···H2v3.5512
C2···C9ii3.581 (14)C7···H4ii3.3859
C3···O1ii3.587 (12)C10···H3viii3.3078
C3···C6v3.451 (13)C10···H3ii3.3304
C3···C9ii3.346 (12)C10···H4vii3.1352
C4···C1ii3.329 (13)H1···I2iv3.3483
C4···C2ii3.580 (11)H1···O1iv3.5832
C4···C7v3.518 (13)H1···C4ii3.3938
C4···C9v3.413 (12)H1···C5ii3.5387
C5···O1v3.557 (10)H1···H2ii3.4018
C5···O3ii3.492 (12)H2···I1i3.0877
C5···C2ii3.571 (11)H2···C1ii3.4833
C5···C9v3.539 (13)H2···C7v3.5512
C5···C10ii3.421 (11)H2···H1ii3.4018
C6···O3ix3.381 (8)H2···H2i3.5393
C6···O3ii3.531 (13)H3···O3ix2.4768
C6···C3v3.451 (13)H3···O3ii3.4952
C6···C8v3.526 (13)H3···C3v3.4417
C6···C10ii3.199 (13)H3···C10ix3.3078
C7···O2ii3.585 (10)H3···C10ii3.3304
C7···C4v3.518 (13)H3···H3x3.5106
C7···C8v3.533 (11)H3···H4ix3.2916
C7···C10ii3.574 (14)H3···H4ii3.1545
C8···C1ii3.548 (14)H4···I1viii3.2019
C8···C2ii3.577 (12)H4···O3vii2.8657
C8···C6v3.526 (13)H4···C6ii3.1756
C8···C7v3.533 (11)H4···C7ii3.3859
C9···O2ii3.599 (10)H4···C10vii3.1352
C9···C2ii3.581 (14)H4···H3viii3.2916
C9···C3ii3.346 (12)H4···H3ii3.1545
C9···C4v3.413 (12)H4···H4vii3.4680
C1—O1—C9117.8 (5)C3—C8—C4119.6 (6)
O1—C1—C2126.0 (7)C3—C8—C9121.5 (6)
C1—C2—C3120.3 (6)C4—C8—C9118.9 (6)
C1—C2—C10119.5 (7)O1—C9—C7116.8 (6)
C3—C2—C10120.2 (6)O1—C9—C8121.5 (6)
O2—C3—C2123.5 (6)C7—C9—C8121.7 (6)
O2—C3—C8123.7 (7)O3—C10—C2125.0 (7)
C2—C3—C8112.8 (5)O1—C1—H1116.984
C5—C4—C8119.7 (6)C2—C1—H1116.981
I1—C5—C4119.2 (5)C5—C4—H2120.173
I1—C5—C6119.6 (5)C8—C4—H2120.164
C4—C5—C6121.1 (7)C5—C6—H3120.281
C5—C6—C7119.4 (6)C7—C6—H3120.280
I2—C7—C6119.1 (5)O3—C10—H4117.476
I2—C7—C9121.7 (5)C2—C10—H4117.479
C6—C7—C9119.2 (6)
C1—O1—C9—C7−178.3 (7)C8—C4—C5—I1176.2 (7)
C1—O1—C9—C82.2 (11)C8—C4—C5—C6−1.5 (13)
C9—O1—C1—C2−1.6 (13)H2—C4—C5—I1−3.8
C9—O1—C1—H1178.5H2—C4—C5—C6178.5
O1—C1—C2—C3−0.3 (14)H2—C4—C8—C31.8
O1—C1—C2—C10177.4 (8)H2—C4—C8—C9−179.1
H1—C1—C2—C3179.7I1—C5—C6—C7−176.9 (5)
H1—C1—C2—C10−2.6I1—C5—C6—H33.1
C1—C2—C3—O2179.9 (8)C4—C5—C6—C70.9 (13)
C1—C2—C3—C81.4 (12)C4—C5—C6—H3−179.1
C1—C2—C10—O37.6 (14)C5—C6—C7—I2−179.4 (7)
C1—C2—C10—H4−172.4C5—C6—C7—C90.4 (13)
C3—C2—C10—O3−174.7 (8)H3—C6—C7—I20.6
C3—C2—C10—H45.3H3—C6—C7—C9−179.6
C10—C2—C3—O22.3 (13)I2—C7—C9—O1−0.7 (11)
C10—C2—C3—C8−176.3 (7)I2—C7—C9—C8178.8 (5)
O2—C3—C8—C4−0.2 (13)C6—C7—C9—O1179.5 (7)
O2—C3—C8—C9−179.3 (8)C6—C7—C9—C8−1.0 (13)
C2—C3—C8—C4178.4 (7)C3—C8—C9—O1−1.1 (12)
C2—C3—C8—C9−0.7 (11)C3—C8—C9—C7179.5 (7)
C5—C4—C8—C3−178.2 (7)C4—C8—C9—O1179.8 (7)
C5—C4—C8—C90.9 (12)C4—C8—C9—C70.3 (12)
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