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ISSN: 2056-9890

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

aDepartment of Chemistry, Valliammai Engineering College, SRM Nagar, Chennai 603 203, India, bDepartment of Chemistry, Presidency College, Chennai 600 005, India, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dDepartment of Physics, Presidency College, Chennai 600 005, India
*Correspondence e-mail: manivan_1999@yahoo.com

(Received 14 July 2008; accepted 18 July 2008; online 23 July 2008)

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[Chenera, B., West, M. L., Finkelstein, J. A. & Dreyer, G. B. J. (1993). J. Org. Chem. 58, 5605-5606.]); Ellis (1997[Ellis, G. P. (1997). Chromenes, Chromanones and Chromones. New York: John Wiley and Sons Inc.]); Kang et al. (2004[Kang, J.-G., Shin, S.-Y., Kim, M.-J., Bajpai, V., Maheswari, D. K. & Kang, S.-C. (2004). J. Antibiot. 57, 726-731.]); Kooijman et al. (1984[Kooijman, H., Spek, A. L., Kleijn, H., van Maanen, H. L., Jastrzebski, J. T. B. H. & van Kozikowski, A. P. (1984). Acc. Chem. Res. 17, 410-416.]); Marx et al. (2007[Marx, A., Suresh, R., Kanagam, C. C., Manivannan, V. & Büyükgüngör, O. (2007). Acta Cryst. E63, o4530.]); Puviarasan et al. (1998[Puviarasan, K., Govindasamy, L., Velmurugan, D., Shanmuga Sundara Raj, S., Shanmuga Sundaram, M., Raghunathan, R. & Fun, H.-K. (1998). Acta Cryst. C54, 961-963.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20O7S

  • Mr = 452.46

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.958, Tmax = 0.969

  • 24478 measured reflections

  • 5093 independent reflections

  • 3932 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O2 0.93 2.59 2.949 (3) 103
C22—H22⋯O3 0.93 2.56 2.985 (2) 108
C9—H9⋯O2i 0.93 2.58 3.240 (2) 129
C12—H12⋯O5ii 0.93 2.60 3.510 (2) 168
Symmetry codes: (i) -x, -y+1, -z+1; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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 CC 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).

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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.
2-(5,7-Dimethoxy-4-oxo-4H-chromen-2-yl)phenyl 4-toluenesulfonate top
Crystal data top
C24H20O7SF(000) = 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 = 1.7–28.0°
b = 21.011 (6) ŵ = 0.20 mm1
c = 13.969 (4) ÅT = 295 K
β = 98.972 (5)°Block, colourless
V = 2137.6 (10) Å30.22 × 0.18 × 0.16 mm
Z = 4
Data collection top
Bruker Kappa APEXII
diffractometer
5093 independent reflections
Radiation source: fine-focus sealed tube3932 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and ϕ scansθmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.958, Tmax = 0.969k = 2727
24478 measured reflectionsl = 1718
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.7841P]
where P = (Fo2 + 2Fc2)/3
5093 reflections(Δ/σ)max < 0.001
292 parametersΔρmax = 0.27 e Å3
1 restraintΔρmin = 0.38 e Å3
Crystal data top
C24H20O7SV = 2137.6 (10) Å3
Mr = 452.46Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.373 (2) ŵ = 0.20 mm1
b = 21.011 (6) ÅT = 295 K
c = 13.969 (4) Å0.22 × 0.18 × 0.16 mm
β = 98.972 (5)°
Data collection top
Bruker Kappa APEXII
diffractometer
5093 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3932 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.969Rint = 0.027
24478 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0501 restraint
wR(F2) = 0.126H-atom parameters constrained
S = 1.05Δρmax = 0.27 e Å3
5093 reflectionsΔρmin = 0.38 e Å3
292 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
O20.0424 (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)
H60.01880.68920.46510.067*
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) top
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, º) top
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—C22140.30 (19)
O2—S1—O3—C845.51 (14)C8—C13—C14—C2239.1 (3)
C1—S1—O3—C870.87 (13)C12—C13—C14—O437.4 (2)
O1—S1—C1—C6157.58 (18)C8—C13—C14—O4143.28 (16)
O2—S1—C1—C622.09 (19)C14—O4—C15—C16179.20 (15)
O3—S1—C1—C693.54 (17)C14—O4—C15—C200.6 (2)
O1—S1—C1—C226.1 (2)O4—C15—C16—C17178.01 (16)
O2—S1—C1—C2161.64 (16)C20—C15—C16—C172.2 (3)
O3—S1—C1—C282.74 (17)C23—O6—C17—C164.5 (3)
C6—C1—C2—C31.3 (3)C23—O6—C17—C18174.7 (2)
S1—C1—C2—C3174.95 (16)C15—C16—C17—O6179.71 (19)
C1—C2—C3—C40.4 (3)C15—C16—C17—C181.1 (3)
C2—C3—C4—C52.1 (3)O6—C17—C18—C19178.11 (18)
C2—C3—C4—C7177.7 (2)C16—C17—C18—C191.1 (3)
C3—C4—C5—C62.1 (3)C24—O7—C19—C185.0 (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—C5174.92 (16)C17—C18—C19—C202.5 (3)
C4—C5—C6—C10.4 (3)O4—C15—C20—C19179.33 (15)
S1—O3—C8—C977.99 (17)C16—C15—C20—C190.9 (2)
S1—O3—C8—C13104.39 (16)O4—C15—C20—C210.9 (2)
C13—C8—C9—C101.4 (3)C16—C15—C20—C21178.93 (17)
O3—C8—C9—C10178.93 (15)O7—C19—C20—C15178.12 (15)
C8—C9—C10—C110.8 (3)C18—C19—C20—C151.5 (2)
C9—C10—C11—C121.7 (3)O7—C19—C20—C211.6 (2)
C10—C11—C12—C130.4 (3)C18—C19—C20—C21178.72 (17)
C11—C12—C13—C81.7 (3)C15—C20—C21—O5178.16 (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—C12179.87 (15)C19—C20—C21—C22179.25 (16)
C9—C8—C13—C14176.78 (16)O4—C14—C22—C212.8 (3)
O3—C8—C13—C140.8 (2)C13—C14—C22—C21179.82 (17)
C15—O4—C14—C221.2 (2)O5—C21—C22—C14176.42 (19)
C15—O4—C14—C13179.02 (13)C20—C21—C22—C142.3 (3)
Hydrogen-bond geometry (Å, º) top
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, z1/2.

Experimental details

Crystal data
Chemical formulaC24H20O7S
Mr452.46
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)7.373 (2), 21.011 (6), 13.969 (4)
β (°) 98.972 (5)
V3)2137.6 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.22 × 0.18 × 0.16
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.958, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
24478, 5093, 3932
Rint0.027
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.126, 1.05
No. of reflections5093
No. of parameters292
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.38

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
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, z1/2.
 

Acknowledgements

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

References

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