8-Formyl-4-methyl-2-oxo-2H-chromen-7-yl 4-methyl­benzenesulfonate

Yuvaraj, H.; Gayathri, D.; Kalkhambkar, R.G.; Kulkarni, G.M.; Bapset, R.M.

doi:10.1107/S1600536811018927

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1513

doi:10.1107/S1600536811018927

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8-Formyl-4-methyl-2-oxo-2H-chromen-7-yl 4-methylbenzenesulfonate

H. Yuvaraj,^a ^* D. Gayathri,^b Rajesh G. Kalkhambkar,^c Geeta M. Kulkarni ^c and Rajendra M. Bapset ^d

^aSchool of Display and Chemical Engineering, Yeungnam University, Gyeongsan, Gyeoungbuk 712-749, Republic of Korea, ^bDepartment of Physics, Dr. M.G.R. Educational and Research Institute University, Periyar E.V.R. High Road, Maduravoyal, Chennai 600 095, India, ^cDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad 580 001, Karnataka, India, and ^dDepartment of Chemistry, B.K. College, Belgaum 590 001, Karnataka, India
^*Correspondence e-mail: yuvraj_pd@yahoo.co.in

(Received 18 April 2011; accepted 18 May 2011; online 25 May 2011)

In the title compound, C₁₈H₁₄O₆S, the coumarin ring system is nearly planar, with a maximum out-of-plane deviation of 0.032 (2) Å. The dihedral angle between the benzene ring and the coumarin ring system is 32.41 (8)°. The crystal packing is stabilized by intermolecular C—H⋯O interactions, generating C(8), C(10) and C(11) chains and an R₂²(10) ring. The formyl group is disordered over two sets of sites, with occupancies of 0.548 (5) and 0.452 (5).

Related literature

For the biological activity of coumarins, see: Carlton et al. (1996 ); El-Agrody et al. (2001 ); Emmanuel-Giota et al. (2001 ); Kulkarni et al. (2006 ); Kalkhambkar et al. (2008 ); Shaker (1996 ); Yang et al. (2005 ); Zhou et al. (2000 ). For a related structure, see: Yuvaraj et al. (2011 ).

Experimental

Crystal data

C₁₈H₁₄O₆S
M_r = 358.35
Orthorhombic, P b c a
a = 17.6174 (7) Å
b = 7.2025 (3) Å
c = 25.7706 (10) Å
V = 3270.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.14 × 0.13 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
48911 measured reflections
4234 independent reflections
3095 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.135
S = 1.02
4234 reflections
238 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O6ⁱ	0.93	2.56	3.326 (2)	140
C13—H13⋯O6ⁱⁱ	0.93	2.52	3.343 (2)	148
C16—H16⋯O2ⁱⁱⁱ	0.93	2.51	3.433 (2)	175
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018927/is2704sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018927/is2704Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018927/is2704Isup3.cml

checkCIF report

Comment top

Coumarins are the class of lactones with extensive occurrence in plants possessing wide range of biological activities (Kulkarni et al., 2006). Many synthetic and naturally occurring coumarins are well documented for their wide range of biological activities such as antibacterial (El-Agrody et al., 2001), antifungal (Shaker, 1996), antioxidant (Yang et al., 2005), analgesic (Kalkhambkar et al., 2008) and anti-inflammatory (Emmanuel-Giota et al., 2001) properties. A large number of natural and semisynthetic coumarin and bicoumarin derivatives have been reported to demonstrate chemopreventive (Carlton et al., 1996) and anti-HIV (Zhou et al., 2000) activities. In view of various biological properties associated with coumarins, we have synthesized the title compound and report here its structure.

The molecular structure of the title compound is shown in Fig.1. Bond lengths and bond angles are comparable with the similar structure (Yuvaraj et al., 2011). Positional disorder has been observed for formyl oxygen atom with C14—O4A and C14—O4B bond lengths being 1.137 (3) and 1.109 (4) Å, respectively. The coumarin ring system is nearly planar with a maximum out-of-plane deviation of 0.032 (2) Å (r.m.s. deviation = 0.021 Å). Dihedral angle between the C2–C7 benzene ring and the C8–C13 benzene ring of the coumarin moeity is 33.3 (1)°. Atoms O6 and C18 lie -0.017 (3) and 0.073 (3) Å, respectively, from the least-squares plane of the atoms (C10/C11/C17/C16/C15/O5, r.m.s. deviation = 0.012 Å). Atom C1 lies 0.030 (4) Å from the least-squares plane of the phenyl ring (r.m.s. deviation = 0.007 Å).

The crystal packing is stabilized by C—H···O intermolecular interactions. C4—H4···O6ⁱ interaction generates a helical C(11) chain along the [010] direction. Interactions C13—H13···O6ⁱⁱ and C16—H16···O2ⁱⁱⁱ generate C(8) and C(10) chains, respectively, running along [100]. In addition, the interactions C13—H13···O6ⁱⁱ and C16—H16···O2ⁱⁱⁱ generate an R₂²(10) ring.

Related literature top

For the biological activity of coumarins, see: Carlton et al. (1996); El-Agrody et al. (2001); Emmanuel-Giota et al. (2001); Kulkarni et al. (2006); Kalkhambkar et al. (2008); Shaker (1996); Yang et al. (2005); Zhou et al. (2000). For a related structure, see: Yuvaraj et al. (2011).

Experimental top

A mixture of 8-formyl-7-hydroxy-4-methyl coumarin (6 mmol), p-toluenesulfonylchloride (6 mmol) and powdered anhydrous K₂CO₃ (6 mmol) in 20 ml of super dry acetone was stirred in room temperature for 12 h. After the completion of the reaction, the solvent was removed under reduced pressure and separated the solids by filtration. It was then washed with 50 ml of dilute hydrochloric acid, excess of cold water, dried and crystallized from ethanol and dioxan mixture. Yield 80%; Light green crystalline solid (ethanol + dioxan); m.p. 180–182 °C; R_f 0.43 (benzene); IR (KBr) cm^-1 1734, 1708, 1303; ¹H NMR (CDCl₃) δ 2.47 (3H, s), 2.51 (3H, s), 6.35 (1H, s), 7.32 (6H, m), 10.34 (1H, s); Anal. Calcd. for C₁₈H₁₄O₆S: C 60.33, H 3.94; Found: C 60.13, H 3.70.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of the title compound, showing the C—H···O interactions (dashed lines). For clarity, hydrogen atoms which are not involved in hydrogen bonding are omitted.

8-Formyl-4-methyl-2-oxo-2H-chromen-7-yl 4-methylbenzenesulfonate top

Crystal data top

C₁₈H₁₄O₆S	F(000) = 1488
M_r = 358.35	D_x = 1.456 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6552 reflections
a = 17.6174 (7) Å	θ = 2.3–26.6°
b = 7.2025 (3) Å	µ = 0.23 mm⁻¹
c = 25.7706 (10) Å	T = 293 K
V = 3270.0 (2) Å³	Plate, colorless
Z = 8	0.14 × 0.13 × 0.13 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3095 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 28.7°, θ_min = 1.6°
ϕ and ω scans	h = −23→23
48911 measured reflections	k = −9→9
4234 independent reflections	l = −34→34

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0672P)² + 0.8242P] where P = (F_o² + 2F_c²)/3
4234 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.26 e Å⁻³
14 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₈H₁₄O₆S	V = 3270.0 (2) Å³
M_r = 358.35	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.6174 (7) Å	µ = 0.23 mm⁻¹
b = 7.2025 (3) Å	T = 293 K
c = 25.7706 (10) Å	0.14 × 0.13 × 0.13 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3095 reflections with I > 2σ(I)
48911 measured reflections	R_int = 0.037
4234 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	14 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	Δρ_max = 0.26 e Å⁻³
4234 reflections	Δρ_min = −0.37 e Å⁻³
238 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.70245 (18)	0.5004 (5)	0.48070 (11)	0.1076 (9)
H1A	0.7160	0.4100	0.4550	0.161*
H1B	0.7446	0.5202	0.5037	0.161*
H1C	0.6895	0.6152	0.4639	0.161*
C2	0.63513 (13)	0.4313 (3)	0.51137 (8)	0.0712 (5)
C3	0.62555 (11)	0.4882 (3)	0.56260 (8)	0.0652 (5)
H3	0.6605	0.5692	0.5773	0.078*
C4	0.56508 (10)	0.4264 (3)	0.59184 (7)	0.0585 (4)
H4	0.5587	0.4663	0.6259	0.070*
C5	0.51398 (10)	0.3038 (2)	0.56962 (7)	0.0563 (4)
C6	0.52174 (14)	0.2479 (3)	0.51834 (8)	0.0708 (5)
H6	0.4866	0.1677	0.5034	0.085*
C7	0.58218 (16)	0.3130 (3)	0.49004 (8)	0.0791 (6)
H7	0.5875	0.2763	0.4556	0.095*
C8	0.54138 (10)	0.0811 (3)	0.67455 (7)	0.0578 (4)
C9	0.61696 (10)	0.0624 (2)	0.65996 (6)	0.0525 (4)
C10	0.67090 (9)	0.1065 (2)	0.69784 (6)	0.0472 (3)
C11	0.65136 (9)	0.1600 (2)	0.74813 (6)	0.0495 (4)
C12	0.57417 (11)	0.1691 (3)	0.76024 (7)	0.0631 (5)
H12	0.5595	0.2012	0.7937	0.076*
C13	0.51960 (10)	0.1319 (3)	0.72389 (8)	0.0680 (5)
H13	0.4684	0.1408	0.7324	0.082*
C14	0.63965 (14)	−0.0075 (4)	0.60842 (8)	0.0772 (6)
H14A	0.6916	0.0009	0.6025	0.093*	0.548 (5)
H14B	0.5992	−0.0394	0.5871	0.093*	0.452 (5)
C15	0.80427 (9)	0.1381 (2)	0.71607 (7)	0.0534 (4)
C16	0.78344 (10)	0.1945 (2)	0.76774 (7)	0.0550 (4)
H16	0.8220	0.2264	0.7907	0.066*
C17	0.71185 (10)	0.2035 (2)	0.78441 (6)	0.0513 (4)
C18	0.69355 (13)	0.2552 (3)	0.83935 (7)	0.0720 (5)
H18A	0.7398	0.2772	0.8581	0.108*
H18B	0.6660	0.1558	0.8555	0.108*
H18C	0.6631	0.3658	0.8396	0.108*
O1	0.38782 (9)	0.1146 (3)	0.57769 (7)	0.0957 (6)
O2	0.41980 (9)	0.3388 (2)	0.64607 (6)	0.0814 (4)
O3	0.48511 (7)	0.03917 (19)	0.63759 (6)	0.0685 (4)
O4A	0.60724 (19)	−0.0694 (4)	0.57442 (11)	0.0912 (13)	0.548 (5)
O4B	0.6962 (2)	−0.0293 (10)	0.59052 (17)	0.136 (2)	0.452 (5)
O5	0.74534 (6)	0.09179 (18)	0.68306 (4)	0.0539 (3)
O6	0.86731 (7)	0.1254 (2)	0.69874 (6)	0.0738 (4)
S1	0.44287 (3)	0.20842 (8)	0.60799 (2)	0.06651 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.113 (2)	0.114 (2)	0.0953 (18)	0.0111 (18)	0.0263 (16)	0.0339 (16)
C2	0.0815 (14)	0.0662 (12)	0.0660 (11)	0.0140 (10)	0.0039 (10)	0.0138 (10)
C3	0.0622 (11)	0.0601 (10)	0.0735 (12)	0.0003 (9)	−0.0090 (9)	0.0002 (9)
C4	0.0580 (10)	0.0607 (10)	0.0569 (9)	0.0028 (8)	−0.0095 (8)	−0.0079 (8)
C5	0.0581 (9)	0.0538 (9)	0.0570 (9)	0.0043 (8)	−0.0142 (8)	−0.0006 (7)
C6	0.0929 (15)	0.0587 (10)	0.0607 (10)	0.0035 (10)	−0.0224 (10)	−0.0065 (9)
C7	0.1139 (18)	0.0721 (13)	0.0513 (10)	0.0132 (13)	−0.0026 (11)	−0.0005 (9)
C8	0.0468 (8)	0.0596 (10)	0.0671 (10)	−0.0013 (7)	−0.0085 (7)	0.0120 (8)
C9	0.0506 (9)	0.0523 (9)	0.0546 (9)	0.0037 (7)	−0.0045 (7)	0.0034 (7)
C10	0.0425 (8)	0.0477 (8)	0.0513 (8)	0.0046 (6)	−0.0005 (6)	0.0047 (6)
C11	0.0489 (8)	0.0501 (8)	0.0496 (8)	0.0055 (7)	0.0010 (7)	0.0078 (7)
C12	0.0554 (10)	0.0788 (12)	0.0549 (9)	0.0106 (9)	0.0095 (8)	0.0116 (9)
C13	0.0442 (9)	0.0882 (14)	0.0715 (11)	0.0044 (9)	0.0055 (8)	0.0176 (10)
C14	0.0680 (13)	0.0969 (16)	0.0667 (12)	0.0167 (12)	−0.0161 (11)	−0.0185 (11)
C15	0.0473 (8)	0.0543 (9)	0.0588 (9)	0.0035 (7)	−0.0040 (7)	0.0000 (7)
C16	0.0550 (9)	0.0540 (9)	0.0559 (9)	0.0008 (7)	−0.0089 (7)	−0.0021 (7)
C17	0.0589 (9)	0.0468 (8)	0.0483 (8)	0.0035 (7)	−0.0022 (7)	0.0030 (7)
C18	0.0799 (13)	0.0841 (13)	0.0519 (9)	0.0003 (11)	0.0025 (9)	−0.0045 (9)
O1	0.0631 (9)	0.1010 (12)	0.1230 (14)	−0.0170 (8)	−0.0409 (9)	0.0130 (10)
O2	0.0605 (8)	0.0953 (11)	0.0884 (10)	0.0165 (8)	0.0070 (7)	0.0052 (9)
O3	0.0530 (7)	0.0674 (8)	0.0850 (9)	−0.0080 (6)	−0.0181 (6)	0.0112 (7)
O4A	0.111 (3)	0.084 (2)	0.0780 (19)	0.0174 (17)	−0.0341 (17)	−0.0248 (15)
O4B	0.078 (3)	0.241 (6)	0.089 (3)	−0.013 (3)	0.016 (2)	−0.065 (3)
O5	0.0435 (6)	0.0660 (7)	0.0522 (6)	0.0061 (5)	−0.0009 (5)	−0.0045 (5)
O6	0.0454 (7)	0.0988 (11)	0.0773 (9)	0.0045 (7)	0.0020 (6)	−0.0126 (8)
S1	0.0460 (2)	0.0741 (3)	0.0795 (3)	−0.0003 (2)	−0.0156 (2)	0.0070 (2)

Geometric parameters (Å, º) top

C1—C2	1.510 (3)	C11—C12	1.397 (2)
C1—H1A	0.9600	C11—C17	1.452 (2)
C1—H1B	0.9600	C12—C13	1.369 (3)
C1—H1C	0.9600	C12—H12	0.9300
C2—C7	1.378 (3)	C13—H13	0.9300
C2—C3	1.393 (3)	C14—O4B	1.109 (4)
C3—C4	1.379 (3)	C14—O4A	1.137 (3)
C3—H3	0.9300	C14—H14A	0.9300
C4—C5	1.385 (2)	C14—H14B	0.9300
C4—H4	0.9300	C15—O6	1.200 (2)
C5—C6	1.388 (3)	C15—O5	1.383 (2)
C5—S1	1.737 (2)	C15—C16	1.440 (2)
C6—C7	1.373 (3)	C16—C17	1.334 (2)
C6—H6	0.9300	C16—H16	0.9300
C7—H7	0.9300	C17—C18	1.499 (2)
C8—C13	1.378 (3)	C18—H18A	0.9600
C8—C9	1.390 (2)	C18—H18B	0.9600
C8—O3	1.407 (2)	C18—H18C	0.9600
C9—C10	1.399 (2)	O1—S1	1.4165 (16)
C9—C14	1.476 (3)	O2—S1	1.4179 (17)
C10—O5	1.3696 (19)	O3—S1	1.6191 (14)
C10—C11	1.395 (2)

C2—C1—H1A	109.5	C12—C11—C17	124.09 (16)
C2—C1—H1B	109.5	C13—C12—C11	121.44 (17)
H1A—C1—H1B	109.5	C13—C12—H12	119.3
C2—C1—H1C	109.5	C11—C12—H12	119.3
H1A—C1—H1C	109.5	C12—C13—C8	119.21 (17)
H1B—C1—H1C	109.5	C12—C13—H13	120.4
C7—C2—C3	118.6 (2)	C8—C13—H13	120.4
C7—C2—C1	121.8 (2)	O4B—C14—C9	131.8 (3)
C3—C2—C1	119.6 (2)	O4A—C14—C9	133.7 (3)
C4—C3—C2	121.12 (19)	C9—C14—H14A	113.1
C4—C3—H3	119.4	C9—C14—H14B	114.2
C2—C3—H3	119.4	O6—C15—O5	116.59 (16)
C3—C4—C5	118.82 (17)	O6—C15—C16	126.95 (16)
C3—C4—H4	120.6	O5—C15—C16	116.45 (15)
C5—C4—H4	120.6	C17—C16—C15	123.55 (16)
C4—C5—C6	120.96 (19)	C17—C16—H16	118.2
C4—C5—S1	119.03 (14)	C15—C16—H16	118.2
C6—C5—S1	119.89 (16)	C16—C17—C11	118.42 (15)
C7—C6—C5	118.9 (2)	C16—C17—C18	121.31 (17)
C7—C6—H6	120.6	C11—C17—C18	120.27 (16)
C5—C6—H6	120.6	C17—C18—H18A	109.5
C6—C7—C2	121.63 (19)	C17—C18—H18B	109.5
C6—C7—H7	119.2	H18A—C18—H18B	109.5
C2—C7—H7	119.2	C17—C18—H18C	109.5
C13—C8—C9	122.83 (17)	H18A—C18—H18C	109.5
C13—C8—O3	119.04 (16)	H18B—C18—H18C	109.5
C9—C8—O3	118.08 (17)	C8—O3—S1	118.74 (12)
C8—C9—C10	116.10 (16)	C10—O5—C15	121.95 (13)
C8—C9—C14	122.41 (17)	O1—S1—O2	120.07 (11)
C10—C9—C14	121.43 (16)	O1—S1—O3	102.44 (9)
O5—C10—C11	121.05 (14)	O2—S1—O3	107.72 (9)
O5—C10—C9	116.03 (14)	O1—S1—C5	111.62 (10)
C11—C10—C9	122.91 (15)	O2—S1—C5	109.80 (10)
C10—C11—C12	117.44 (16)	O3—S1—C5	103.55 (8)
C10—C11—C17	118.47 (15)

C7—C2—C3—C4	0.8 (3)	C8—C9—C14—O4B	179.2 (6)
C1—C2—C3—C4	−179.4 (2)	C10—C9—C14—O4B	−3.5 (7)
C2—C3—C4—C5	0.9 (3)	C8—C9—C14—O4A	−7.1 (5)
C3—C4—C5—C6	−2.0 (3)	C10—C9—C14—O4A	170.2 (3)
C3—C4—C5—S1	173.98 (14)	O6—C15—C16—C17	−179.34 (19)
C4—C5—C6—C7	1.5 (3)	O5—C15—C16—C17	0.0 (3)
S1—C5—C6—C7	−174.49 (16)	C15—C16—C17—C11	−2.1 (3)
C5—C6—C7—C2	0.3 (3)	C15—C16—C17—C18	177.28 (18)
C3—C2—C7—C6	−1.4 (3)	C10—C11—C17—C16	1.5 (2)
C1—C2—C7—C6	178.9 (2)	C12—C11—C17—C16	−178.16 (18)
C13—C8—C9—C10	−2.8 (3)	C10—C11—C17—C18	−177.90 (17)
O3—C8—C9—C10	179.68 (15)	C12—C11—C17—C18	2.5 (3)
C13—C8—C9—C14	174.6 (2)	C13—C8—O3—S1	80.5 (2)
O3—C8—C9—C14	−2.9 (3)	C9—C8—O3—S1	−101.90 (18)
C8—C9—C10—O5	−178.68 (15)	C11—C10—O5—C15	−3.4 (2)
C14—C9—C10—O5	3.9 (3)	C9—C10—O5—C15	177.47 (15)
C8—C9—C10—C11	2.2 (2)	O6—C15—O5—C10	−177.79 (16)
C14—C9—C10—C11	−175.20 (18)	C16—C15—O5—C10	2.8 (2)
O5—C10—C11—C12	−179.13 (16)	C8—O3—S1—O1	−175.87 (15)
C9—C10—C11—C12	−0.1 (3)	C8—O3—S1—O2	−48.35 (16)
O5—C10—C11—C17	1.2 (2)	C8—O3—S1—C5	67.94 (15)
C9—C10—C11—C17	−179.74 (15)	C4—C5—S1—O1	169.10 (15)
C10—C11—C12—C13	−1.7 (3)	C6—C5—S1—O1	−14.87 (19)
C17—C11—C12—C13	177.95 (18)	C4—C5—S1—O2	33.42 (17)
C11—C12—C13—C8	1.2 (3)	C6—C5—S1—O2	−150.56 (16)
C9—C8—C13—C12	1.2 (3)	C4—C5—S1—O3	−81.39 (16)
O3—C8—C13—C12	178.67 (18)	C6—C5—S1—O3	94.64 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O6ⁱ	0.93	2.56	3.326 (2)	140
C13—H13···O6ⁱⁱ	0.93	2.52	3.343 (2)	148
C16—H16···O2ⁱⁱⁱ	0.93	2.51	3.433 (2)	175

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄O₆S
M_r	358.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	17.6174 (7), 7.2025 (3), 25.7706 (10)
V (Å³)	3270.0 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.14 × 0.13 × 0.13

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	48911, 4234, 3095
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.135, 1.02
No. of reflections	4234
No. of parameters	238
No. of restraints	14
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.37

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O6ⁱ	0.93	2.56	3.326 (2)	140
C13—H13···O6ⁱⁱ	0.93	2.52	3.343 (2)	148
C16—H16···O2ⁱⁱⁱ	0.93	2.51	3.433 (2)	175

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

Acknowledgements

HY acknowledges Yeungnam University for the opportunity to work as a Full-Time Foreign Instructor.

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