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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1576.
Published online 2008 July 23. doi:  10.1107/S1600536808022654
PMCID: PMC2962194

2-(5,7-Dimeth­oxy-4-oxo-4H-chromen-2-yl)phenyl 4-toluene­sulfonate

Abstract

In the crystal structure of the title compound, C24H20O7S, the chromone system makes a dihedral angle of 37.32 (7)° with the adjacent benzene ring. The chromone ring system and the tolyl ring are almost parallel, with a dihedral angle of 4.56 (9)°. The tolyl ring is twisted at an angle of 41.75 (6)° with respect to the benzene ring. Weak intra- and inter­molecular C—H(...)O inter­actions are observed.

Related literature

For related literature, see: Chenera et al. (1993 [triangle]); Ellis (1997 [triangle]); Kang et al. (2004 [triangle]); Kooijman et al. (1984 [triangle]); Marx et al. (2007 [triangle]); Puviarasan et al. (1998 [triangle]).

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Object name is e-64-o1576-scheme1.jpg

Experimental

Crystal data

  • C24H20O7S
  • M r = 452.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1576-efi1.jpg
  • a = 7.373 (2) Å
  • b = 21.011 (6) Å
  • c = 13.969 (4) Å
  • β = 98.972 (5)°
  • V = 2137.6 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 295 (2) K
  • 0.22 × 0.18 × 0.16 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.958, T max = 0.969
  • 24478 measured reflections
  • 5093 independent reflections
  • 3932 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.126
  • S = 1.05
  • 5093 reflections
  • 292 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022654/is2315sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022654/is2315Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge Professor T. N. Guru Row and Dr Vijay Thiruvenkatam, Indian Institute of Science, Bangalore, India, for the data collection.

supplementary crystallographic information

Comment

Chromanone derivatives are versatile intermediates for the synthesis of natural products such as brazillin, hematoxylin, ripariochromene, clausenin (Kooijman et al., 1984; Ellis, 1997; Chenera et al., 1993). The title compound, (I), (Fig. 1) has both the sulfonate and flavanone moieties. Hence, it has the structural characteristics of both of them. The geometric parameters of the sulfonate moiety agree with the reported values of similar sulfonates (Kang et al., 2004; Marx et al., 2007; Puviarasan et al., 1998)

The flavanone moiety resembles the chromanone which consists of one benzene ring fused with a six membered oxygen pyranone ring. In chromanone there is an exocyclic double bond at the 4-position of the pyranone ring. In the flavone, there is an endocyclic C═C double bond in the pyranone ring. This brings about a large change in the conformation of pyranone ring.

The pyranone ring is inclined to the benzene C8–C13 ring at an angle of 37.42 (5)°, while the benzene C15—C20 ring and the pyranone ring are co-planar. The flavone and tolyl rings are almost lying in parallel planes, with a dihedral angle of 4.56 (9)°. The tolyl ring makes a dihedral angle of 41.75 (6)° with the benzene C8–C13 ring. The molecular structure is stabilized by the weak intramolecular C—H···O interactions and the crystal packing is stabilized by the weak intermolecular C—H···O interactions (Table 1) (Fig. 2).

Experimental

Phluroglucinol was converted to phluroaceto phenone by Hoesch reaction. The latter on treatment with o-nitro benzoyl chloride, potassium carbonate and acetone afforded nitro flavone. This was methylated and reduced with Tin/con HCl to get amino flavone. Diazotization followed by hydrolysis yielded flavonol. Sulfonylation, in presence of triethyl amine and acetone resulted in 5,7 – dimethoxy-2'-flavonyl-4-sulfonate. Diffraction quality crystals were obtained by recrystallizing the crude product from an ethanol solution.

Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3. A rigid bond restraint (DELU) was applied for atoms C3 and C4 in the final cycle of the refinement.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C24H20O7SF000 = 944
Mr = 452.46Dx = 1.406 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5023 reflections
a = 7.373 (2) Åθ = 1.7–28.0º
b = 21.011 (6) ŵ = 0.20 mm1
c = 13.969 (4) ÅT = 295 (2) K
β = 98.972 (5)ºBlock, colourless
V = 2137.6 (10) Å30.22 × 0.18 × 0.16 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer5093 independent reflections
Radiation source: fine-focus sealed tube3932 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 295(2) Kθmax = 28.0º
ω and [var phi] scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.958, Tmax = 0.969k = −27→27
24478 measured reflectionsl = −17→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.126  w = 1/[σ2(Fo2) + (0.0523P)2 + 0.7841P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
5093 reflectionsΔρmax = 0.27 e Å3
292 parametersΔρmin = −0.38 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.08488 (8)0.62413 (2)0.64071 (4)0.05905 (18)
O10.0797 (3)0.61918 (9)0.74090 (14)0.0966 (7)
O2−0.0424 (2)0.58983 (7)0.57276 (15)0.0778 (5)
O30.28958 (18)0.59915 (6)0.63318 (9)0.0471 (3)
O40.53667 (17)0.74321 (5)0.50458 (8)0.0405 (3)
O50.7115 (2)0.75407 (7)0.79509 (10)0.0666 (4)
O60.6757 (3)0.95793 (6)0.44864 (11)0.0699 (5)
O70.8015 (2)0.87641 (7)0.76660 (9)0.0541 (4)
C10.0892 (3)0.70374 (9)0.60523 (15)0.0476 (5)
C20.1605 (3)0.74935 (10)0.67212 (18)0.0602 (5)
H20.19730.73870.73680.072*
C30.1758 (3)0.81123 (10)0.6404 (2)0.0666 (6)
H30.22280.84230.68480.080*
C40.1234 (3)0.82809 (10)0.5447 (2)0.0651 (6)
C50.0488 (3)0.78228 (11)0.48044 (18)0.0630 (6)
H50.00920.79330.41610.076*
C60.0313 (3)0.71989 (10)0.50952 (16)0.0556 (5)
H6−0.01880.68920.46510.067*
C70.1486 (4)0.89585 (12)0.5117 (3)0.0992 (11)
H7A0.16680.89570.44510.149*
H7B0.25370.91440.55100.149*
H7C0.04120.92030.51800.149*
C80.3393 (2)0.59138 (7)0.54037 (12)0.0373 (4)
C90.2781 (2)0.53817 (8)0.48695 (14)0.0430 (4)
H90.20390.50850.51160.052*
C100.3279 (3)0.52929 (9)0.39678 (14)0.0462 (4)
H100.28860.49330.36060.055*
C110.4361 (3)0.57390 (9)0.36046 (14)0.0468 (4)
H110.46690.56840.29890.056*
C120.4992 (3)0.62672 (8)0.41444 (13)0.0427 (4)
H120.57270.65630.38900.051*
C130.4541 (2)0.63623 (8)0.50660 (12)0.0363 (4)
C140.5303 (2)0.69218 (7)0.56371 (12)0.0355 (4)
C150.6059 (2)0.79985 (7)0.54323 (12)0.0355 (4)
C160.6061 (3)0.84733 (8)0.47443 (13)0.0431 (4)
H160.56620.83950.40900.052*
C170.6678 (3)0.90651 (8)0.50682 (14)0.0464 (4)
C180.7306 (3)0.91772 (9)0.60496 (14)0.0463 (4)
H180.76970.95830.62550.056*
C190.7350 (2)0.86942 (8)0.67109 (13)0.0399 (4)
C200.6689 (2)0.80742 (8)0.64181 (12)0.0352 (4)
C210.6642 (3)0.75290 (8)0.70711 (13)0.0416 (4)
C220.5923 (3)0.69490 (8)0.65831 (13)0.0425 (4)
H220.58950.65810.69490.051*
C230.6289 (5)0.94826 (13)0.34712 (18)0.1037 (12)
H23A0.71020.91730.32630.156*
H23B0.64020.98770.31390.156*
H23C0.50470.93320.33260.156*
C240.8834 (4)0.93587 (12)0.79739 (17)0.0718 (7)
H24A0.98370.94430.76280.108*
H24B0.92820.93430.86570.108*
H24C0.79360.96910.78440.108*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0666 (3)0.0429 (3)0.0766 (4)−0.0102 (2)0.0393 (3)−0.0010 (2)
O10.1372 (18)0.0811 (12)0.0899 (13)0.0014 (12)0.0750 (13)0.0146 (10)
O20.0545 (9)0.0495 (9)0.1352 (16)−0.0205 (7)0.0327 (9)−0.0202 (9)
O30.0596 (8)0.0376 (7)0.0469 (7)−0.0034 (6)0.0164 (6)0.0059 (5)
O40.0558 (8)0.0302 (6)0.0347 (6)−0.0089 (5)0.0051 (5)−0.0008 (5)
O50.1040 (13)0.0593 (9)0.0336 (7)−0.0095 (8)0.0011 (7)−0.0001 (6)
O60.1180 (14)0.0340 (7)0.0570 (9)−0.0143 (8)0.0117 (9)0.0049 (6)
O70.0637 (9)0.0567 (8)0.0416 (7)−0.0160 (7)0.0071 (6)−0.0158 (6)
C10.0453 (10)0.0370 (9)0.0641 (13)−0.0033 (8)0.0197 (9)−0.0086 (8)
C20.0599 (13)0.0533 (12)0.0673 (14)0.0019 (10)0.0098 (10)−0.0162 (10)
C30.0526 (12)0.0453 (12)0.1012 (14)−0.0042 (9)0.0095 (12)−0.0269 (11)
C40.0437 (11)0.0445 (11)0.1110 (15)0.0029 (9)0.0248 (11)0.0005 (12)
C50.0588 (13)0.0569 (13)0.0756 (15)0.0076 (10)0.0176 (11)0.0057 (11)
C60.0522 (12)0.0483 (11)0.0675 (14)−0.0034 (9)0.0130 (10)−0.0119 (10)
C70.0805 (18)0.0483 (14)0.179 (3)0.0009 (13)0.054 (2)0.0132 (17)
C80.0411 (9)0.0301 (8)0.0408 (9)0.0028 (7)0.0066 (7)0.0045 (7)
C90.0416 (9)0.0295 (8)0.0569 (11)−0.0021 (7)0.0046 (8)0.0035 (7)
C100.0445 (10)0.0349 (9)0.0569 (11)−0.0015 (7)0.0004 (8)−0.0103 (8)
C110.0493 (11)0.0479 (10)0.0434 (10)−0.0011 (8)0.0081 (8)−0.0098 (8)
C120.0464 (10)0.0375 (9)0.0457 (10)−0.0055 (7)0.0113 (8)−0.0018 (7)
C130.0381 (9)0.0298 (8)0.0407 (9)−0.0002 (6)0.0051 (7)−0.0001 (7)
C140.0385 (9)0.0307 (8)0.0384 (9)−0.0018 (6)0.0099 (7)0.0018 (6)
C150.0384 (9)0.0303 (8)0.0388 (9)−0.0031 (6)0.0090 (7)−0.0047 (7)
C160.0567 (11)0.0361 (9)0.0360 (9)−0.0053 (8)0.0055 (8)−0.0011 (7)
C170.0577 (11)0.0334 (9)0.0497 (11)−0.0048 (8)0.0134 (9)0.0008 (8)
C180.0532 (11)0.0342 (9)0.0538 (11)−0.0094 (8)0.0152 (9)−0.0120 (8)
C190.0378 (9)0.0427 (9)0.0409 (9)−0.0039 (7)0.0115 (7)−0.0106 (7)
C200.0348 (8)0.0369 (8)0.0352 (8)−0.0023 (6)0.0094 (6)−0.0047 (7)
C210.0455 (10)0.0437 (10)0.0359 (9)−0.0012 (8)0.0073 (7)−0.0010 (7)
C220.0511 (10)0.0357 (9)0.0409 (10)−0.0031 (7)0.0080 (8)0.0048 (7)
C230.196 (4)0.0525 (14)0.0567 (15)−0.0225 (18)0.0020 (18)0.0179 (12)
C240.0765 (16)0.0766 (16)0.0605 (14)−0.0301 (13)0.0054 (12)−0.0266 (12)

Geometric parameters (Å, °)

S1—O11.4099 (19)C9—C101.379 (3)
S1—O21.4226 (18)C9—H90.9300
S1—O31.6168 (15)C10—C111.378 (3)
S1—C11.746 (2)C10—H100.9300
O3—C81.411 (2)C11—C121.381 (3)
O4—C141.3588 (19)C11—H110.9300
O4—C151.3720 (19)C12—C131.394 (2)
O5—C211.224 (2)C12—H120.9300
O6—C171.359 (2)C13—C141.481 (2)
O6—C231.421 (3)C14—C221.331 (2)
O7—C191.356 (2)C15—C161.385 (2)
O7—C241.425 (2)C15—C201.392 (2)
C1—C61.381 (3)C16—C171.376 (2)
C1—C21.384 (3)C16—H160.9300
C2—C31.384 (3)C17—C181.397 (3)
C2—H20.9300C18—C191.369 (3)
C3—C41.378 (4)C18—H180.9300
C3—H30.9300C19—C201.428 (2)
C4—C51.372 (3)C20—C211.468 (2)
C4—C71.517 (3)C21—C221.455 (2)
C5—C61.384 (3)C22—H220.9300
C5—H50.9300C23—H23A0.9600
C6—H60.9300C23—H23B0.9600
C7—H7A0.9600C23—H23C0.9600
C7—H7B0.9600C24—H24A0.9600
C7—H7C0.9600C24—H24B0.9600
C8—C91.380 (2)C24—H24C0.9600
C8—C131.397 (2)
O1—S1—O2120.53 (12)C11—C12—C13120.71 (16)
O1—S1—O3102.15 (11)C11—C12—H12119.6
O2—S1—O3108.53 (9)C13—C12—H12119.6
O1—S1—C1110.91 (11)C12—C13—C8117.38 (15)
O2—S1—C1109.59 (11)C12—C13—C14119.07 (15)
O3—S1—C1103.52 (8)C8—C13—C14123.54 (15)
C8—O3—S1118.44 (11)C22—C14—O4122.06 (15)
C14—O4—C15119.42 (13)C22—C14—C13127.71 (15)
C17—O6—C23117.19 (16)O4—C14—C13110.19 (14)
C19—O7—C24117.60 (16)O4—C15—C16113.08 (14)
C6—C1—C2120.7 (2)O4—C15—C20122.33 (14)
C6—C1—S1119.57 (15)C16—C15—C20124.59 (15)
C2—C1—S1119.57 (17)C17—C16—C15117.29 (16)
C1—C2—C3118.4 (2)C17—C16—H16121.4
C1—C2—H2120.8C15—C16—H16121.4
C3—C2—H2120.8O6—C17—C16124.38 (17)
C4—C3—C2121.8 (2)O6—C17—C18114.47 (16)
C4—C3—H3119.1C16—C17—C18121.14 (17)
C2—C3—H3119.1C19—C18—C17120.43 (16)
C5—C4—C3118.5 (2)C19—C18—H18119.8
C5—C4—C7121.0 (3)C17—C18—H18119.8
C3—C4—C7120.5 (3)O7—C19—C18123.41 (16)
C4—C5—C6121.2 (2)O7—C19—C20115.82 (16)
C4—C5—H5119.4C18—C19—C20120.77 (16)
C6—C5—H5119.4C15—C20—C19115.71 (15)
C1—C6—C5119.2 (2)C15—C20—C21119.27 (15)
C1—C6—H6120.4C19—C20—C21125.01 (15)
C5—C6—H6120.4O5—C21—C22120.86 (17)
C4—C7—H7A109.5O5—C21—C20125.27 (17)
C4—C7—H7B109.5C22—C21—C20113.86 (15)
H7A—C7—H7B109.5C14—C22—C21123.01 (16)
C4—C7—H7C109.5C14—C22—H22118.5
H7A—C7—H7C109.5C21—C22—H22118.5
H7B—C7—H7C109.5O6—C23—H23A109.5
C9—C8—C13121.86 (16)O6—C23—H23B109.5
C9—C8—O3118.74 (15)H23A—C23—H23B109.5
C13—C8—O3119.35 (14)O6—C23—H23C109.5
C10—C9—C8119.51 (16)H23A—C23—H23C109.5
C10—C9—H9120.2H23B—C23—H23C109.5
C8—C9—H9120.2O7—C24—H24A109.5
C11—C10—C9119.76 (16)O7—C24—H24B109.5
C11—C10—H10120.1H24A—C24—H24B109.5
C9—C10—H10120.1O7—C24—H24C109.5
C10—C11—C12120.73 (17)H24A—C24—H24C109.5
C10—C11—H11119.6H24B—C24—H24C109.5
C12—C11—H11119.6
O1—S1—O3—C8173.84 (13)C12—C13—C14—C22−140.30 (19)
O2—S1—O3—C845.51 (14)C8—C13—C14—C2239.1 (3)
C1—S1—O3—C8−70.87 (13)C12—C13—C14—O437.4 (2)
O1—S1—C1—C6−157.58 (18)C8—C13—C14—O4−143.28 (16)
O2—S1—C1—C6−22.09 (19)C14—O4—C15—C16179.20 (15)
O3—S1—C1—C693.54 (17)C14—O4—C15—C20−0.6 (2)
O1—S1—C1—C226.1 (2)O4—C15—C16—C17178.01 (16)
O2—S1—C1—C2161.64 (16)C20—C15—C16—C17−2.2 (3)
O3—S1—C1—C2−82.74 (17)C23—O6—C17—C16−4.5 (3)
C6—C1—C2—C3−1.3 (3)C23—O6—C17—C18174.7 (2)
S1—C1—C2—C3174.95 (16)C15—C16—C17—O6−179.71 (19)
C1—C2—C3—C4−0.4 (3)C15—C16—C17—C181.1 (3)
C2—C3—C4—C52.1 (3)O6—C17—C18—C19−178.11 (18)
C2—C3—C4—C7−177.7 (2)C16—C17—C18—C191.1 (3)
C3—C4—C5—C6−2.1 (3)C24—O7—C19—C18−5.0 (3)
C7—C4—C5—C6177.7 (2)C24—O7—C19—C20174.65 (18)
C2—C1—C6—C51.3 (3)C17—C18—C19—O7177.12 (17)
S1—C1—C6—C5−174.92 (16)C17—C18—C19—C20−2.5 (3)
C4—C5—C6—C10.4 (3)O4—C15—C20—C19−179.33 (15)
S1—O3—C8—C9−77.99 (17)C16—C15—C20—C190.9 (2)
S1—O3—C8—C13104.39 (16)O4—C15—C20—C210.9 (2)
C13—C8—C9—C10−1.4 (3)C16—C15—C20—C21−178.93 (17)
O3—C8—C9—C10−178.93 (15)O7—C19—C20—C15−178.12 (15)
C8—C9—C10—C11−0.8 (3)C18—C19—C20—C151.5 (2)
C9—C10—C11—C121.7 (3)O7—C19—C20—C211.6 (2)
C10—C11—C12—C13−0.4 (3)C18—C19—C20—C21−178.72 (17)
C11—C12—C13—C8−1.7 (3)C15—C20—C21—O5−178.16 (19)
C11—C12—C13—C14177.69 (16)C19—C20—C21—O52.1 (3)
C9—C8—C13—C122.6 (3)C15—C20—C21—C220.5 (2)
O3—C8—C13—C12−179.87 (15)C19—C20—C21—C22−179.25 (16)
C9—C8—C13—C14−176.78 (16)O4—C14—C22—C212.8 (3)
O3—C8—C13—C140.8 (2)C13—C14—C22—C21−179.82 (17)
C15—O4—C14—C22−1.2 (2)O5—C21—C22—C14176.42 (19)
C15—O4—C14—C13−179.02 (13)C20—C21—C22—C14−2.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O20.932.592.949 (3)103
C22—H22···O30.932.562.985 (2)108
C9—H9···O2i0.932.583.240 (2)129
C12—H12···O5ii0.932.603.510 (2)168

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2315).

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