Literature DB >> 24860363

6-Bromo-4-oxo-4H-chromene-3-carb-alde-hyde.

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H5BrO3, a brominated 3-formyl-chromone derivative, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.0420 Å), with the largest deviation from its mean plane [0.109 (2) Å] being found for the ring-bound carbonyl O atom. In the crystal, mol-ecules are linked through halogen bonds [Br⋯O = 3.191 (2) Å, C-Br⋯O = 167.32 (10)° and C=O⋯Br = 168.4 (2)°] along [101]. Mol-ecules are assembled into layers parallel to (101) via π-π stacking inter-actions along the b axis [shortest centroid-centroid distance between the pyran and benzene rings = 3.495 (2) Å].

Entities:  

Year:  2014        PMID： 24860363      PMCID： PMC4011302          DOI： 10.1107/S160053681400796X

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 ▶).

Experimental

Crystal data

C10H5BrO3 M = 253.05 Triclinic, a = 6.5743 (18) Å b = 6.967 (3) Å c = 10.350 (4) Å α = 71.02 (3)° β = 85.53 (3)° γ = 70.67 (3)° V = 422.8 (3) Å3 Z = 2 Mo Kα radiation μ = 4.85 mm−1 T = 100 K 0.42 × 0.40 × 0.38 mm

Data collection

Rigaku AFC-7R diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.135, T max = 0.159 2389 measured reflections 1944 independent reflections 1880 reflections with F 2 > 2σ(F 2) R int = 0.024 3 standard reflections every 150 reflections intensity decay: 2.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.077 S = 1.16 1944 reflections 128 parameters H-atom parameters constrained Δρmax = 1.05 e Å−3 Δρmin = −0.74 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/S160053681400796X/tk5306sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400796X/tk5306Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S160053681400796X/tk5306Isup3.cml CCDC reference: 996416 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H5BrO3Z = 2
Mr = 253.05F(000) = 248.00
Triclinic, P1Dx = 1.988 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 6.5743 (18) ÅCell parameters from 25 reflections
b = 6.967 (3) Åθ = 15.2–17.4°
c = 10.350 (4) ŵ = 4.85 mm−1
α = 71.02 (3)°T = 100 K
β = 85.53 (3)°Block, colorless
γ = 70.67 (3)°0.42 × 0.40 × 0.38 mm
V = 422.8 (3) Å3
Rigaku AFC-7R diffractometerRint = 0.024
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)h = −8→8
Tmin = 0.135, Tmax = 0.159k = −5→9
2389 measured reflectionsl = −12→13
1944 independent reflections3 standard reflections every 150 reflections
1880 reflections with F2 > 2σ(F2) intensity decay: 2.0%
Refinement on F2Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.077w = 1/[σ2(Fo2) + (0.0545P)2 + 0.1959P] where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max = 0.001
1944 reflectionsΔρmax = 1.05 e Å−3
128 parametersΔρmin = −0.74 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.151 (9)
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
Br10.09454 (3)0.28528 (3)0.922893 (19)0.01450 (13)
O10.8085 (3)0.1862 (3)0.52565 (16)0.0122 (3)
O20.1989 (3)0.3151 (3)0.38347 (17)0.0157 (4)
O30.6969 (3)0.2664 (3)0.11860 (18)0.0203 (4)
C10.7668 (4)0.2190 (4)0.3943 (3)0.0120 (4)
C20.5687 (4)0.2640 (3)0.3402 (2)0.0101 (4)
C30.3797 (4)0.2830 (3)0.4253 (2)0.0100 (4)
C40.2621 (4)0.2805 (3)0.6624 (2)0.0106 (4)
C50.3145 (4)0.2506 (4)0.7956 (3)0.0112 (4)
C60.5287 (4)0.1952 (4)0.8394 (3)0.0136 (4)
C70.6918 (4)0.1709 (4)0.7478 (3)0.0132 (4)
C80.4269 (3)0.2578 (4)0.5684 (2)0.0092 (4)
C90.6393 (4)0.2048 (3)0.6128 (3)0.0107 (4)
C100.5462 (4)0.2943 (4)0.1932 (3)0.0145 (4)
H10.88460.21000.33470.0143*
H20.11620.31590.63470.0127*
H30.56140.17440.93180.0163*
H40.83780.13150.77650.0158*
H50.40500.33820.15500.0174*
U11U22U33U12U13U23
Br10.01323 (17)0.01865 (17)0.01105 (16)−0.00255 (10)0.00148 (9)−0.00690 (10)
O10.0070 (7)0.0168 (8)0.0124 (8)−0.0032 (6)−0.0008 (6)−0.0044 (6)
O20.0099 (7)0.0254 (9)0.0140 (8)−0.0066 (6)−0.0013 (6)−0.0079 (7)
O30.0184 (8)0.0302 (10)0.0172 (9)−0.0093 (7)0.0048 (7)−0.0133 (8)
C10.0107 (9)0.0122 (9)0.0133 (10)−0.0034 (8)0.0011 (8)−0.0050 (8)
C20.0104 (9)0.0089 (9)0.0120 (10)−0.0032 (7)−0.0000 (8)−0.0045 (7)
C30.0103 (9)0.0085 (9)0.0118 (10)−0.0032 (7)−0.0012 (8)−0.0037 (7)
C40.0095 (9)0.0104 (9)0.0126 (10)−0.0032 (7)−0.0001 (8)−0.0047 (8)
C50.0122 (9)0.0110 (9)0.0116 (10)−0.0040 (7)0.0019 (8)−0.0055 (7)
C60.0154 (10)0.0122 (10)0.0139 (10)−0.0045 (8)−0.0037 (8)−0.0043 (8)
C70.0107 (9)0.0144 (10)0.0143 (11)−0.0041 (8)−0.0038 (8)−0.0035 (8)
C80.0087 (9)0.0085 (8)0.0117 (10)−0.0035 (7)0.0001 (8)−0.0043 (7)
C90.0095 (9)0.0088 (9)0.0135 (10)−0.0032 (7)0.0004 (8)−0.0032 (7)
C100.0153 (10)0.0174 (10)0.0139 (10)−0.0069 (8)0.0005 (8)−0.0075 (8)
Br1—C51.888 (3)C4—C81.403 (3)
O1—C11.338 (3)C5—C61.401 (4)
O1—C91.375 (3)C6—C71.380 (4)
O2—C31.221 (3)C7—C91.391 (4)
O3—C101.211 (3)C8—C91.395 (3)
C1—C21.356 (4)C1—H10.950
C2—C31.461 (3)C4—H20.950
C2—C101.478 (4)C6—H30.950
C3—C81.480 (4)C7—H40.950
C4—C51.379 (4)C10—H50.950
O1···C32.868 (3)C9···H13.1828
O2···C13.572 (3)C9···H23.2719
O2···C42.869 (3)C9···H33.2502
O2···C102.894 (3)C10···H12.5537
O3···C12.820 (4)H1···H53.4881
C1···C73.574 (4)H3···H42.3392
C1···C82.757 (3)Br1···H3xi3.1998
C2···C92.768 (4)Br1···H4vi2.9904
C4···C72.805 (4)Br1···H4xi3.4343
C5···C92.748 (4)Br1···H5x3.4515
C6···C82.795 (4)Br1···H5vii3.4131
Br1···O3i3.191 (2)O1···H1ii2.8201
O1···O1ii3.117 (3)O1···H2iii2.9005
O1···O2iii3.104 (3)O1···H2v3.5064
O1···O2iv3.325 (3)O2···H1vi2.5430
O1···C1ii3.174 (3)O2···H2vii2.6756
O1···C4v3.479 (3)O3···H3ix2.5290
O1···C8v3.488 (3)O3···H3v3.5734
O2···O1vi3.104 (3)O3···H4ii3.3419
O2···O1iv3.325 (3)O3···H5xii3.1712
O2···C1vi3.113 (4)C1···H2v3.4876
O2···C4vii3.325 (3)C3···H2vii3.4612
O2···C9iv3.408 (4)C4···H1v3.3664
O3···Br1viii3.191 (2)C4···H4vi3.2949
O3···C5iv3.444 (4)C5···H1v3.3731
O3···C6ix3.408 (4)C5···H3xi3.2745
C1···O1ii3.174 (3)C5···H4vi3.5319
C1···O2iii3.113 (4)C6···H3xi3.0684
C1···C4v3.285 (4)C6···H5iv3.5775
C1···C5v3.455 (4)C6···H5v3.4388
C1···C8v3.581 (4)C7···H1ii3.4259
C2···C4iv3.591 (4)C7···H2iii3.2813
C2···C5v3.530 (4)C9···H1ii3.4206
C2···C6v3.478 (4)C9···H2iii3.5095
C2···C7v3.566 (4)C10···H3ix3.0662
C2···C8iv3.437 (4)C10···H3v3.3423
C3···C3iv3.568 (3)H1···O1ii2.8201
C3···C7v3.525 (4)H1···O2iii2.5430
C3···C8iv3.535 (4)H1···C4v3.3664
C3···C9iv3.588 (4)H1···C5v3.3731
C3···C9v3.422 (4)H1···C7ii3.4259
C4···O1v3.479 (3)H1···C9ii3.4206
C4···O2vii3.325 (3)H1···H2iv3.5756
C4···C1v3.285 (4)H1···H2v3.4176
C4···C2iv3.591 (4)H1···H4ii2.9827
C4···C10iv3.594 (4)H2···O1vi2.9005
C5···O3iv3.444 (4)H2···O1v3.5064
C5···C1v3.455 (4)H2···O2vii2.6756
C5···C2v3.530 (4)H2···C1v3.4876
C5···C10iv3.563 (4)H2···C3vii3.4612
C6···O3x3.408 (4)H2···C7vi3.2813
C6···C2v3.478 (4)H2···C9vi3.5095
C6···C10v3.331 (4)H2···H1iv3.5756
C7···C2v3.566 (4)H2···H1v3.4176
C7···C3v3.525 (4)H2···H2vii3.1789
C8···O1v3.488 (3)H2···H4vi2.6584
C8···C1v3.581 (4)H3···Br1xi3.1998
C8···C2iv3.437 (4)H3···O3x2.5290
C8···C3iv3.535 (4)H3···O3v3.5734
C8···C9v3.494 (4)H3···C5xi3.2745
C9···O2iv3.408 (4)H3···C6xi3.0684
C9···C3iv3.588 (4)H3···C10x3.0662
C9···C3v3.422 (4)H3···C10v3.3423
C9···C8v3.494 (4)H3···H3xi2.7283
C10···C4iv3.594 (4)H3···H5x2.8751
C10···C5iv3.563 (4)H3···H5v3.2964
C10···C6v3.331 (4)H4···Br1iii2.9904
Br1···H22.9161H4···Br1xi3.4343
Br1···H32.9076H4···O3ii3.3419
O1···H42.5120H4···C4iii3.2949
O2···H22.6160H4···C5iii3.5319
O2···H52.6169H4···H1ii2.9827
O3···H12.4933H4···H2iii2.6584
C1···H53.2796H5···Br1ix3.4515
C3···H13.2958H5···Br1vii3.4131
C3···H22.6880H5···O3xii3.1712
C3···H52.6959H5···C6iv3.5775
C4···H33.2780H5···C6v3.4388
C5···H43.2671H5···H3ix2.8751
C6···H23.2828H5···H3v3.2964
C8···H43.2883
C1—O1—C9118.51 (18)C4—C8—C9118.9 (2)
O1—C1—C2124.7 (2)O1—C9—C7116.04 (19)
C1—C2—C3120.7 (2)O1—C9—C8122.2 (2)
C1—C2—C10119.0 (2)C7—C9—C8121.7 (2)
C3—C2—C10120.3 (2)O3—C10—C2124.0 (3)
O2—C3—C2123.6 (3)O1—C1—H1117.637
O2—C3—C8122.6 (2)C2—C1—H1117.636
C2—C3—C8113.81 (19)C5—C4—H2120.442
C5—C4—C8119.1 (2)C8—C4—H2120.436
Br1—C5—C4119.78 (16)C5—C6—H3120.165
Br1—C5—C6118.71 (18)C7—C6—H3120.161
C4—C5—C6121.5 (2)C6—C7—H4120.488
C5—C6—C7119.7 (3)C9—C7—H4120.487
C6—C7—C9119.0 (2)O3—C10—H5118.015
C3—C8—C4121.2 (2)C2—C10—H5118.010
C3—C8—C9119.87 (19)
C1—O1—C9—C7−179.47 (17)C8—C4—C5—Br1178.91 (17)
C1—O1—C9—C8−0.5 (3)C8—C4—C5—C6−1.0 (4)
C9—O1—C1—C2−1.9 (3)H2—C4—C5—Br1−1.1
C9—O1—C1—H1178.1H2—C4—C5—C6179.0
O1—C1—C2—C30.8 (4)H2—C4—C8—C3−1.5
O1—C1—C2—C10−179.35 (18)H2—C4—C8—C9−179.7
H1—C1—C2—C3−179.2Br1—C5—C6—C7−179.45 (14)
H1—C1—C2—C100.6Br1—C5—C6—H30.6
C1—C2—C3—O2−177.1 (2)C4—C5—C6—C70.4 (4)
C1—C2—C3—C82.4 (3)C4—C5—C6—H3−179.6
C1—C2—C10—O35.5 (4)C5—C6—C7—C90.8 (4)
C1—C2—C10—H5−174.5C5—C6—C7—H4−179.2
C3—C2—C10—O3−174.6 (2)H3—C6—C7—C9−179.2
C3—C2—C10—H55.4H3—C6—C7—H40.8
C10—C2—C3—O23.0 (4)C6—C7—C9—O1177.51 (19)
C10—C2—C3—C8−177.47 (18)C6—C7—C9—C8−1.5 (4)
O2—C3—C8—C4−3.2 (4)H4—C7—C9—O1−2.5
O2—C3—C8—C9174.99 (19)H4—C7—C9—C8178.5
C2—C3—C8—C4177.26 (17)C3—C8—C9—O13.8 (4)
C2—C3—C8—C9−4.5 (3)C3—C8—C9—C7−177.29 (18)
C5—C4—C8—C3178.50 (18)C4—C8—C9—O1−177.99 (18)
C5—C4—C8—C90.3 (3)C4—C8—C9—C71.0 (4)
  8 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Principles and applications of halogen bonding in medicinal chemistry and chemical biology.

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3.  Halogen bonding based recognition processes: a world parallel to hydrogen bonding.

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4.  Halogen bonds in biological molecules.

Authors:  Pascal Auffinger; Franklin A Hays; Eric Westhof; P Shing Ho
Journal:  Proc Natl Acad Sci U S A       Date:  2004-11-19       Impact factor: 11.205

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

Authors:  Suman Sirimulla; Jake B Bailey; Rahulsimham Vegesna; Mahesh Narayan
Journal:  J Chem Inf Model       Date:  2013-11-13       Impact factor: 4.956

6.  6-Chloro-4-oxo-4H-chromene-3-carb-aldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-05

7.  6,8-Di-chloro-4-oxochromene-3-carbalde-hyde.

Authors:  Yoshinobu Ishikawa; Yuya Motohashi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-08-14

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

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-03-15
  8 in total
  5 in total

1.  Crystal structure of 6-bromo-7-fluoro-4-oxo-4H-chromene-3-carbaldehyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-06-27

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

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-07-15

3.  6-Fluoro-4-oxo-4H-chromene-3-carbalde-hyde.

Authors:  Yoshinobu Ishikawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-18

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

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-06-04

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

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-08-13
  5 in total

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