Literature DB >> 25161541

6-Iodo-4-oxo-4H-chromene-3-carbaldehyde.

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H5IO3, an iodinated 3-formyl-chromone derivative, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.0259 Å), with the largest deviation from the least-squares plane [0.056 (5) Å] being found for the formyl O atom. In the crystal, mol-ecules are linked through I⋯O halogen bonds [I⋯O = 3.245 (4) Å, C-I⋯O = 165.95 (13) and C=O⋯I = 169.7 (4)°] along [101]. The supra-molecular chains are assembled into layers via π-π stacking inter-actions along the b axis [shortest centroid-centroid distance between the pyran and benzene rings = 3.558 (3) Å].

Entities:  

Year:  2014        PMID： 25161541      PMCID： PMC4120610          DOI： 10.1107/S1600536814012471

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


Related literature

For related structures, see: Ishikawa (2014a ▶,b ▶,c ▶). For the synthesis of the precursor of the title compound, see: Bovonsombat et al. (2009 ▶). For halogen bonding, see: Auffinger et al. (2004 ▶); Metrangolo et al. (2005 ▶); Wilcken et al. (2013 ▶); Sirimulla et al. (2013 ▶).

Experimental

Crystal data

C10H5IO3 M = 300.05 Triclinic, a = 6.5741 (17) Å b = 6.798 (3) Å c = 10.437 (5) Å α = 79.03 (3)° β = 86.45 (3)° γ = 76.00 (3)° V = 444.3 (3) Å3 Z = 2 Mo Kα radiation μ = 3.58 mm−1 T = 100 K 0.25 × 0.25 × 0.08 mm

Data collection

Rigaku AFC-7R diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.432, T max = 0.751 2519 measured reflections 2050 independent reflections 1989 reflections with F 2 > 2σ(F 2) R int = 0.014 3 standard reflections every 150 reflections intensity decay: −1.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.104 S = 1.11 2050 reflections 127 parameters H-atom parameters constrained Δρmax = 2.55 e Å−3 Δρmin = −3.59 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: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536814012471/tk5319sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012471/tk5319Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814012471/tk5319Isup3.cml CCDC reference: 1005730 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H5IO3Z = 2
Mr = 300.05F(000) = 284.00
Triclinic, P1Dx = 2.243 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 6.5741 (17) ÅCell parameters from 25 reflections
b = 6.798 (3) Åθ = 15.1–17.0°
c = 10.437 (5) ŵ = 3.58 mm−1
α = 79.03 (3)°T = 100 K
β = 86.45 (3)°Plate, yellow
γ = 76.00 (3)°0.25 × 0.25 × 0.08 mm
V = 444.3 (3) Å3
Rigaku AFC-7R diffractometerRint = 0.014
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)h = −4→8
Tmin = 0.432, Tmax = 0.751k = −8→8
2519 measured reflectionsl = −13→13
2050 independent reflections3 standard reflections every 150 reflections
1989 reflections with F2 > 2σ(F2) intensity decay: −1.8%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0828P)2 + 0.5762P] where P = (Fo2 + 2Fc2)/3
2050 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 2.55 e Å−3
0 restraintsΔρmin = −3.59 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
I10.09130 (3)0.75924 (3)0.412452 (19)0.01417 (14)
O10.7896 (5)0.6863 (5)−0.0188 (3)0.0146 (6)
O20.1807 (5)0.8519 (5)−0.1406 (3)0.0160 (6)
O30.6616 (5)0.7995 (5)−0.4137 (3)0.0204 (7)
C10.7417 (7)0.7311 (6)−0.1454 (5)0.0155 (8)
C20.5449 (6)0.7856 (6)−0.1926 (4)0.0112 (7)
C30.3623 (7)0.8053 (6)−0.1040 (4)0.0112 (7)
C40.2610 (6)0.7778 (6)0.1343 (4)0.0120 (7)
C50.3206 (6)0.7330 (6)0.2634 (4)0.0115 (7)
C60.5314 (7)0.6711 (6)0.2983 (5)0.0136 (8)
C70.6858 (7)0.6540 (6)0.2022 (4)0.0143 (8)
C80.4172 (6)0.7620 (5)0.0363 (4)0.0103 (7)
C90.6270 (7)0.7003 (6)0.0722 (4)0.0126 (8)
C100.5169 (7)0.8281 (6)−0.3362 (4)0.0139 (8)
H10.85470.7242−0.20700.0186*
H20.11690.81860.11240.0144*
H30.56840.64090.38770.0163*
H40.82970.61150.22460.0172*
H50.37880.8801−0.36890.0167*
U11U22U33U12U13U23
I10.01465 (19)0.01545 (19)0.01309 (19)−0.00418 (12)0.00051 (11)−0.00369 (11)
O10.0083 (12)0.0180 (14)0.0178 (14)−0.0035 (10)−0.0002 (11)−0.0035 (11)
O20.0100 (13)0.0212 (14)0.0155 (13)−0.0030 (11)−0.0019 (10)−0.0004 (11)
O30.0206 (15)0.0224 (15)0.0188 (15)−0.0056 (12)0.0051 (12)−0.0062 (12)
C10.0130 (17)0.0118 (17)0.023 (2)−0.0053 (14)0.0004 (15)−0.0038 (15)
C20.0137 (17)0.0075 (16)0.0139 (18)−0.0043 (13)−0.0011 (14)−0.0025 (13)
C30.0104 (17)0.0062 (15)0.0172 (19)−0.0024 (13)−0.0024 (14)−0.0015 (13)
C40.0117 (17)0.0085 (16)0.0167 (18)−0.0032 (13)−0.0010 (14)−0.0033 (13)
C50.0136 (17)0.0076 (15)0.0139 (17)−0.0041 (13)0.0002 (13)−0.0015 (12)
C60.0143 (19)0.0115 (17)0.0156 (18)−0.0038 (14)−0.0032 (15)−0.0018 (14)
C70.0120 (17)0.0129 (17)0.0185 (19)−0.0025 (14)−0.0035 (14)−0.0034 (14)
C80.0129 (17)0.0034 (14)0.0146 (19)−0.0027 (12)−0.0017 (14)−0.0001 (12)
C90.0124 (17)0.0097 (16)0.017 (2)−0.0037 (13)−0.0016 (15)−0.0042 (14)
C100.0145 (17)0.0130 (17)0.0144 (19)−0.0038 (14)0.0003 (14)−0.0023 (14)
I1—C52.100 (4)C4—C81.404 (6)
O1—C11.338 (6)C5—C61.397 (6)
O1—C91.383 (5)C6—C71.383 (6)
O2—C31.224 (5)C7—C91.390 (6)
O3—C101.213 (5)C8—C91.394 (6)
C1—C21.353 (6)C1—H10.950
C2—C31.466 (6)C4—H20.950
C2—C101.485 (6)C6—H30.950
C3—C81.487 (6)C7—H40.950
C4—C51.383 (6)C10—H50.950
O1···C32.876 (5)I1···H4v3.1327
O2···C13.579 (5)I1···H5xi3.3845
O2···C42.877 (6)I1···H5vi3.4429
O2···C102.910 (5)O1···H2iii3.0137
O3···C12.811 (6)O1···H2iv3.5123
C1···C73.575 (7)O2···H1v2.6723
C1···C82.762 (6)O2···H2vi2.6440
C2···C92.774 (6)O2···H4vii3.4433
C4···C72.809 (6)O2···H4iv3.5709
C5···C92.746 (6)O3···H3x2.6765
C6···C82.795 (6)O3···H5ix2.8065
I1···O3i3.245 (4)C1···H2vii3.5802
O1···O1ii3.254 (4)C1···H2iv3.4884
O1···O2iii3.154 (5)C1···H4ii3.3639
O1···C4iv3.554 (5)C3···H2vi3.5381
O2···O1v3.154 (5)C4···H1iv3.5034
O2···C1v3.192 (6)C4···H4v3.3197
O2···C4vi3.358 (5)C5···H1iv3.5345
O2···C7vii3.510 (6)C5···H4v3.5834
O3···I1viii3.245 (4)C6···H5vii3.5870
O3···O3ix3.316 (5)C6···H5iv3.4606
O3···C6x3.494 (6)C7···H1ii3.4570
O3···C10ix3.321 (5)C7···H2iii3.3116
C1···O2iii3.192 (6)C9···H2iii3.5699
C1···C4vii3.444 (6)C10···H3x3.3327
C1···C4iv3.358 (6)C10···H3vii3.5102
C1···C5iv3.548 (6)C10···H3iv3.4573
C2···C5iv3.526 (6)C10···H5ix3.4573
C2···C6iv3.568 (6)H1···O2iii2.6723
C3···C7vii3.555 (7)H1···C4iv3.5034
C3···C7iv3.564 (6)H1···C5iv3.5345
C3···C9vii3.373 (6)H1···C7ii3.4570
C3···C9iv3.457 (7)H1···H2vii3.5954
C4···O1iv3.554 (5)H1···H2iv3.4845
C4···O2vi3.358 (5)H1···H4ii2.7142
C4···C1vii3.444 (6)H2···O1v3.0137
C4···C1iv3.358 (6)H2···O1iv3.5123
C5···C1iv3.548 (6)H2···O2vi2.6440
C5···C2iv3.526 (6)H2···C1vii3.5802
C6···O3xi3.494 (6)H2···C1iv3.4884
C6···C2iv3.568 (6)H2···C3vi3.5381
C6···C10vii3.430 (7)H2···C7v3.3116
C6···C10iv3.438 (7)H2···C9v3.5699
C7···O2vii3.510 (6)H2···H1vii3.5954
C7···C3vii3.555 (7)H2···H1iv3.4845
C7···C3iv3.564 (6)H2···H2vi3.2186
C8···C8iv3.591 (6)H2···H4v2.7025
C8···C9iv3.561 (6)H3···I1xii3.4972
C9···C3vii3.373 (6)H3···O3xi2.6765
C9···C3iv3.457 (7)H3···C10xi3.3327
C9···C8iv3.561 (6)H3···C10vii3.5102
C10···O3ix3.321 (5)H3···C10iv3.4573
C10···C6vii3.430 (7)H3···H3xii2.9731
C10···C6iv3.438 (7)H3···H5xi3.2942
I1···H23.0799H3···H5vii3.5164
I1···H33.0514H3···H5iv3.3247
O1···H42.5116H4···I1iii3.1327
O2···H22.6234H4···O2vii3.4433
O2···H52.6408H4···O2iv3.5709
O3···H12.4759H4···C1ii3.3639
C1···H53.2831H4···C4iii3.3197
C3···H13.2973H4···C5iii3.5834
C3···H22.6956H4···H1ii2.7142
C3···H52.7153H4···H2iii2.7025
C4···H33.2803H5···I1x3.3845
C5···H43.2663H5···I1vi3.4429
C6···H23.2850H5···O3ix2.8065
C8···H43.2886H5···C6vii3.5870
C9···H13.1874H5···C6iv3.4606
C9···H23.2740H5···C10ix3.4573
C9···H33.2505H5···H3x3.2942
C10···H12.5492H5···H3vii3.5164
H1···H53.4835H5···H3iv3.3247
H3···H42.3427H5···H5ix3.4207
I1···H3xii3.4972
C1—O1—C9118.2 (4)C4—C8—C9119.0 (4)
O1—C1—C2125.1 (4)O1—C9—C7115.8 (4)
C1—C2—C3120.7 (4)O1—C9—C8122.3 (4)
C1—C2—C10118.9 (4)C7—C9—C8121.9 (4)
C3—C2—C10120.4 (4)O3—C10—C2123.2 (4)
O2—C3—C2123.7 (4)O1—C1—H1117.453
O2—C3—C8122.5 (4)C2—C1—H1117.444
C2—C3—C8113.7 (4)C5—C4—H2120.591
C5—C4—C8118.8 (4)C8—C4—H2120.596
I1—C5—C4119.9 (3)C5—C6—H3120.161
I1—C5—C6118.4 (3)C7—C6—H3120.160
C4—C5—C6121.7 (4)C6—C7—H4120.551
C5—C6—C7119.7 (4)C9—C7—H4120.551
C6—C7—C9118.9 (4)O3—C10—H5118.395
C3—C8—C4121.2 (4)C2—C10—H5118.392
C3—C8—C9119.8 (4)
C1—O1—C9—C7−179.3 (4)C8—C4—C5—I1179.1 (3)
C1—O1—C9—C8−1.0 (6)C8—C4—C5—C6−0.5 (6)
C9—O1—C1—C2−1.5 (6)H2—C4—C5—I1−0.9
C9—O1—C1—H1178.5H2—C4—C5—C6179.5
O1—C1—C2—C31.7 (6)H2—C4—C8—C3−0.9
O1—C1—C2—C10−179.1 (4)H2—C4—C8—C9−179.5
H1—C1—C2—C3−178.3I1—C5—C6—C7−179.5 (3)
H1—C1—C2—C100.9I1—C5—C6—H30.5
C1—C2—C3—O2−179.2 (4)C4—C5—C6—C70.1 (6)
C1—C2—C3—C80.4 (6)C4—C5—C6—H3−179.9
C1—C2—C10—O36.5 (6)C5—C6—C7—C90.3 (6)
C1—C2—C10—H5−173.5C5—C6—C7—H4−179.7
C3—C2—C10—O3−174.3 (4)H3—C6—C7—C9−179.7
C3—C2—C10—H55.7H3—C6—C7—H40.3
C10—C2—C3—O21.6 (6)C6—C7—C9—O1178.0 (4)
C10—C2—C3—C8−178.7 (3)C6—C7—C9—C8−0.4 (7)
O2—C3—C8—C4−1.6 (6)H4—C7—C9—O1−2.0
O2—C3—C8—C9177.0 (4)H4—C7—C9—C8179.7
C2—C3—C8—C4178.7 (3)C3—C8—C9—O13.1 (6)
C2—C3—C8—C9−2.7 (5)C3—C8—C9—C7−178.7 (4)
C5—C4—C8—C3179.1 (3)C4—C8—C9—O1−178.3 (4)
C5—C4—C8—C90.5 (6)C4—C8—C9—C7−0.1 (6)
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