Ethyl 6-(6-meth­oxy-2-naphth­yl)-2-oxo-4-(2-thien­yl)cyclo­hex-3-ene-1-carboxyl­ate

Li, H.; Mayekar, A.N.; Narayana, B.; Yathirajan, H.S.; Harrison, W.T.A.

doi:10.1107/S1600536809021308

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1533

doi:10.1107/S1600536809021308

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Ethyl 6-(6-methoxy-2-naphthyl)-2-oxo-4-(2-thienyl)cyclohex-3-ene-1-carboxylate

Hongqi Li,^a ^* Anil N. Mayekar,^b B. Narayana,^c H. S. Yathirajan ^b and W. T. A. Harrison ^d

^aKey Laboratory of the Science & Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering & Biotechnology, Donghua University, Shanghai 201620, People's Republic of China, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^dDepartment of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 28 May 2009; accepted 4 June 2009; online 10 June 2009)

The title compound, C₂₄H₂₂O₄S, was prepared by reaction between (2E)-3-(6-methoxy-2-naphthyl)-1-(2-thienyl)prop-2-en-1-one and ethyl acetoacetate. In the crystal, the cyclohexenone ring shows a distorted half-chair conformation. The length of the double bond in the cyclohexenone ring [1.343 (4) Å] is normal.

Related literature

For related structures, see: Fischer et al. (2007a ,b ; 2008a ,b ). For the use of cyclohexenones in organic synthesis, see: Padmavathi et al. (1999 , 2001 ). For pharmaceutical applications of cyclohexenone derivatives, see: Hoye & Tennakoon (2000 ); Hiromichi et al. (2002 ).

Experimental

Crystal data

C₂₄H₂₂O₄S
M_r = 406.48
Monoclinic, P 2₁ /c
a = 18.2501 (4) Å
b = 11.7176 (2) Å
c = 9.6846 (2) Å
β = 93.048 (1)°
V = 2068.10 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 296 K
0.45 × 0.29 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.922, T_max = 0.972
17446 measured reflections
4035 independent reflections
2880 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.202
S = 1.02
4035 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021308/sj2629sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021308/sj2629Isup2.hkl

checkCIF report

Comment top

Cyclohexenones are efficient synthons in building spiro compounds (Padmavathi et al., 2001) or intermediates in the synthesis of benzisoxazole or carbazole derivatives (Padmavathi et al., 1999). Cyclohexenone derivatives are well known lead compounds for the treatment of inflammation and autoimmune diseases (Hoye & Tennakoon, 2000; Hiromichi et al., 2002).

The crystal structures of a series of ethyl 6-substituted 2-oxocyclohex- 3-ene-1-carboxylates have been reported (Fischer et al., 2007; 2007a,b; 2008ab). In view of the importance of these derivatives and continuing our efforts in this field, the title compound, ethyl 6-(6- methoxynaphthalen-2-yl)-2-oxo-4-(2-thienyl)cyclohexa-3-ene-1- carboxylate, was synthesized and its crystal structure is reported in this paper.

Related literature top

For related structures, see: Fischer et al. (2007a,b; 2008a,b). For the use of cyclohexenones in organic synthesis, see: Padmavathi et al. (1999, 2001). For pharmaceutical applications of cyclohexenone derivatives, see: Hoye & Tennakoon (2000); Hiromichi et al. (2002).

Experimental top

(2E)-3-(6-methoxy-2-naphthyl)-1-(2-thienyl)prop-2-en-1-one (1.51 g, 5 mmol) and ethyl acetoacetate (0.65 g, 5 mmol) were refluxed for 6 hr in 10–15 ml of ethanol in the presence of 0.8 ml 10% NaOH. The reaction mixture was cooled to room temperature and the resulting product was filtered and recrystallized from acetonitrile (m.p.: 415–418 K). Analysis % found (calculated): C, 71.19 (71.27); H, 4.94 (4.98); S, 7.89 (7.93).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the crystal structure of the title compound.

Ethyl 6-(6-methoxy-2-naphthyl)-2-oxo-4-(2-thienyl)cyclohex-3-ene-1-carboxylate top

Crystal data top

C₂₄H₂₂O₄S	F(000) = 856
M_r = 406.48	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 415–418 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 18.2501 (4) Å	Cell parameters from 8575 reflections
b = 11.7176 (2) Å	θ = 2.3–28.1°
c = 9.6846 (2) Å	µ = 0.18 mm⁻¹
β = 93.048 (1)°	T = 296 K
V = 2068.10 (7) Å³	Block, colourless
Z = 4	0.45 × 0.29 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4035 independent reflections
Radiation source: fine-focus sealed tube	2880 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −22→22
T_min = 0.922, T_max = 0.972	k = −11→14
17446 measured reflections	l = −11→10

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.095P)² + 0.9907P] where P = (F_o² + 2F_c²)/3
4035 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₄H₂₂O₄S	V = 2068.10 (7) Å³
M_r = 406.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.2501 (4) Å	µ = 0.18 mm⁻¹
b = 11.7176 (2) Å	T = 296 K
c = 9.6846 (2) Å	0.45 × 0.29 × 0.16 mm
β = 93.048 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4035 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2880 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.972	R_int = 0.028
17446 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.202	H-atom parameters constrained
S = 1.02	Δρ_max = 0.26 e Å⁻³
4035 reflections	Δρ_min = −0.38 e Å⁻³
282 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	0.1379 (2)	0.5193 (3)	0.4085 (3)	0.0917 (10)
H1A	0.1524	0.4568	0.4625	0.110*
C2	0.0777 (2)	0.5795 (4)	0.4405 (4)	0.0955 (12)
H2A	0.0516	0.5577	0.5160	0.115*
C3	0.05423 (16)	0.6739 (3)	0.3619 (4)	0.0845 (9)
C4	0.09205 (15)	0.7057 (3)	0.2525 (3)	0.0733 (8)
H4A	0.0762	0.7682	0.1997	0.088*
C5	0.15546 (13)	0.6457 (2)	0.2168 (3)	0.0593 (6)
C6	0.17879 (16)	0.5499 (2)	0.2952 (3)	0.0661 (7)
C7	0.24126 (19)	0.4896 (3)	0.2584 (3)	0.0810 (9)
H7A	0.2567	0.4267	0.3108	0.097*
C8	0.28020 (16)	0.5208 (3)	0.1474 (3)	0.0787 (9)
C9	0.25672 (16)	0.6164 (3)	0.0705 (3)	0.0768 (8)
H9A	0.2829	0.6392	−0.0045	0.092*
C10	0.19634 (15)	0.6766 (3)	0.1033 (3)	0.0694 (7)
H10A	0.1818	0.7393	0.0497	0.083*
C11A	0.3387 (4)	0.4303 (7)	0.1361 (8)	0.0567 (17)	0.489 (11)
H11A	0.3274	0.3649	0.1944	0.068*	0.489 (11)
C11B	0.3537 (3)	0.4735 (6)	0.0866 (7)	0.0498 (15)	0.511 (11)
H11B	0.3642	0.5140	0.0013	0.060*	0.511 (11)
C12	0.41517 (14)	0.4837 (2)	0.1877 (3)	0.0587 (6)
H12A	0.4212	0.5568	0.1426	0.070*
H12B	0.4149	0.4974	0.2864	0.070*
C13	0.47940 (14)	0.4085 (2)	0.1587 (3)	0.0563 (6)
C14	0.47374 (16)	0.3283 (2)	0.0596 (3)	0.0654 (7)
H14A	0.5156	0.2875	0.0396	0.078*
C15	0.40620 (18)	0.3025 (3)	−0.0168 (3)	0.0779 (8)
C16A	0.3403 (3)	0.3921 (6)	−0.0137 (8)	0.0659 (19)	0.511 (11)
H16A	0.3472	0.4565	−0.0763	0.079*	0.511 (11)
C16B	0.3388 (3)	0.3456 (5)	0.0561 (7)	0.0501 (17)	0.489 (11)
H16B	0.3323	0.3031	0.1418	0.060*	0.489 (11)
C17	0.27068 (18)	0.3302 (3)	−0.0483 (4)	0.0771 (8)
C18	0.1848 (5)	0.3678 (7)	−0.2222 (6)	0.190 (3)
H18A	0.1700	0.2910	−0.1987	0.228*
H18B	0.1906	0.3710	−0.3211	0.228*
C19	0.1297 (5)	0.4479 (7)	−0.1848 (8)	0.212 (3)
H19A	0.0839	0.4294	−0.2329	0.317*
H19B	0.1442	0.5236	−0.2095	0.317*
H19C	0.1240	0.4443	−0.0869	0.317*
C20	0.54589 (14)	0.4261 (2)	0.2453 (3)	0.0628 (7)
C21	0.56318 (14)	0.5200 (2)	0.3318 (3)	0.0689 (7)
H21A	0.5331	0.5831	0.3424	0.083*
C22	0.63359 (19)	0.5044 (3)	0.4008 (4)	0.0956 (10)
H22A	0.6556	0.5588	0.4595	0.115*
C23	0.66455 (19)	0.4056 (3)	0.3736 (5)	0.1036 (12)
H23A	0.7098	0.3828	0.4128	0.124*
C24	−0.0321 (3)	0.8260 (6)	0.3341 (8)	0.169 (3)
H24A	−0.0767	0.8524	0.3713	0.254*
H24B	−0.0408	0.8082	0.2379	0.254*
H24C	0.0047	0.8844	0.3443	0.254*
S1	0.61390 (5)	0.32512 (7)	0.26068 (12)	0.0945 (4)
O1	0.2523 (2)	0.3953 (3)	−0.1501 (3)	0.1250 (10)
O2	0.23644 (17)	0.2511 (2)	−0.0137 (3)	0.1130 (9)
O3	−0.00726 (14)	0.7259 (3)	0.4069 (3)	0.1238 (11)
O4	0.40154 (14)	0.2313 (2)	−0.1083 (2)	0.0996 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.127 (3)	0.076 (2)	0.070 (2)	−0.028 (2)	−0.0062 (19)	0.0070 (16)
C2	0.106 (3)	0.110 (3)	0.071 (2)	−0.048 (2)	0.0134 (18)	−0.006 (2)
C3	0.0610 (16)	0.109 (3)	0.084 (2)	−0.0190 (16)	0.0062 (14)	−0.015 (2)
C4	0.0597 (15)	0.080 (2)	0.0794 (18)	0.0007 (13)	−0.0029 (13)	−0.0023 (15)
C5	0.0576 (13)	0.0555 (15)	0.0637 (14)	−0.0041 (11)	−0.0067 (11)	−0.0018 (12)
C6	0.0832 (17)	0.0517 (15)	0.0614 (15)	−0.0115 (13)	−0.0138 (13)	−0.0029 (12)
C7	0.104 (2)	0.0579 (17)	0.077 (2)	0.0198 (16)	−0.0339 (17)	−0.0135 (15)
C8	0.0733 (17)	0.079 (2)	0.080 (2)	0.0214 (15)	−0.0240 (15)	−0.0337 (17)
C9	0.0673 (16)	0.085 (2)	0.0781 (18)	0.0060 (15)	0.0041 (14)	−0.0083 (16)
C10	0.0680 (16)	0.0662 (18)	0.0738 (17)	0.0069 (13)	0.0020 (13)	0.0082 (14)
C11A	0.067 (3)	0.047 (4)	0.056 (4)	−0.003 (3)	0.002 (3)	0.006 (3)
C11B	0.062 (3)	0.037 (3)	0.050 (3)	0.001 (2)	0.003 (2)	0.005 (2)
C12	0.0691 (14)	0.0452 (13)	0.0620 (14)	0.0002 (11)	0.0051 (11)	−0.0005 (11)
C13	0.0683 (14)	0.0429 (13)	0.0588 (14)	0.0007 (10)	0.0134 (11)	0.0065 (11)
C14	0.0757 (16)	0.0535 (15)	0.0682 (16)	0.0077 (12)	0.0151 (13)	−0.0001 (13)
C15	0.089 (2)	0.0624 (17)	0.0824 (19)	0.0045 (15)	0.0099 (15)	−0.0215 (16)
C16A	0.085 (4)	0.052 (4)	0.061 (4)	−0.002 (3)	0.003 (3)	0.002 (3)
C16B	0.068 (3)	0.037 (3)	0.045 (3)	−0.002 (2)	0.001 (2)	0.001 (3)
C17	0.0830 (19)	0.0625 (19)	0.086 (2)	−0.0068 (15)	0.0024 (16)	−0.0232 (17)
C18	0.266 (8)	0.195 (6)	0.103 (4)	0.108 (6)	−0.067 (5)	−0.030 (4)
C19	0.222 (8)	0.195 (7)	0.209 (7)	0.017 (7)	−0.066 (6)	−0.024 (6)
C20	0.0628 (14)	0.0547 (15)	0.0719 (16)	0.0001 (11)	0.0139 (12)	0.0094 (13)
C21	0.0631 (14)	0.0668 (17)	0.0753 (17)	0.0019 (12)	−0.0092 (12)	−0.0095 (14)
C22	0.084 (2)	0.090 (2)	0.110 (3)	−0.0001 (19)	−0.0164 (19)	−0.011 (2)
C23	0.0742 (19)	0.091 (3)	0.144 (3)	−0.0013 (18)	−0.015 (2)	0.014 (2)
C24	0.101 (3)	0.190 (6)	0.220 (6)	0.053 (4)	0.038 (4)	−0.022 (5)
S1	0.0799 (5)	0.0638 (5)	0.1391 (9)	0.0073 (4)	−0.0014 (5)	0.0047 (5)
O1	0.171 (3)	0.105 (2)	0.100 (2)	0.004 (2)	0.022 (2)	0.0166 (17)
O2	0.140 (2)	0.0862 (18)	0.1104 (19)	−0.0330 (17)	−0.0168 (17)	0.0061 (15)
O3	0.0724 (15)	0.181 (3)	0.120 (2)	−0.0047 (18)	0.0278 (15)	−0.032 (2)
O4	0.1168 (18)	0.0868 (16)	0.0945 (16)	0.0164 (13)	−0.0023 (13)	−0.0425 (14)

Geometric parameters (Å, º) top

C1—C2	1.354 (5)	C14—C15	1.436 (4)
C1—C6	1.406 (4)	C14—H14A	0.9300
C1—H1A	0.9300	C15—O4	1.217 (3)
C2—C3	1.396 (5)	C15—C16B	1.536 (6)
C2—H2A	0.9300	C15—C16A	1.599 (7)
C3—C4	1.347 (4)	C16A—C17	1.486 (7)
C3—O3	1.369 (4)	C16A—H16A	0.9800
C4—C5	1.413 (4)	C16B—C17	1.571 (6)
C4—H4A	0.9300	C16B—H16B	0.9800
C5—C10	1.408 (4)	C17—O2	1.176 (4)
C5—C6	1.409 (4)	C17—O1	1.277 (4)
C6—C7	1.403 (4)	C18—O1	1.420 (7)
C7—C8	1.370 (5)	C18—C19	1.437 (9)
C7—H7A	0.9300	C18—H18A	0.9700
C8—C9	1.400 (5)	C18—H18B	0.9700
C8—C11A	1.513 (7)	C19—H19A	0.9600
C8—C11B	1.593 (6)	C19—H19B	0.9600
C9—C10	1.360 (4)	C19—H19C	0.9600
C9—H9A	0.9300	C20—C21	1.409 (4)
C10—H10A	0.9300	C20—S1	1.715 (3)
C11A—C16A	1.520 (8)	C21—C22	1.428 (4)
C11A—C12	1.586 (7)	C21—H21A	0.9300
C11A—H11A	0.9800	C22—C23	1.321 (5)
C11B—C12	1.455 (6)	C22—H22A	0.9300
C11B—C16B	1.549 (7)	C23—S1	1.683 (4)
C11B—H11B	0.9800	C23—H23A	0.9300
C12—C13	1.505 (3)	C24—O3	1.429 (7)
C12—H12A	0.9700	C24—H24A	0.9600
C12—H12B	0.9700	C24—H24B	0.9600
C13—C14	1.343 (4)	C24—H24C	0.9600
C13—C20	1.453 (4)

C2—C1—C6	121.1 (3)	C13—C14—H14A	118.4
C2—C1—H1A	119.5	C15—C14—H14A	118.4
C6—C1—H1A	119.5	O4—C15—C14	123.0 (3)
C1—C2—C3	121.1 (3)	O4—C15—C16B	122.3 (3)
C1—C2—H2A	119.4	C14—C15—C16B	112.3 (3)
C3—C2—H2A	119.4	O4—C15—C16A	116.1 (3)
C4—C3—O3	126.1 (4)	C14—C15—C16A	118.6 (3)
C4—C3—C2	119.5 (3)	C16B—C15—C16A	32.2 (2)
O3—C3—C2	114.4 (3)	C17—C16A—C11A	107.4 (5)
C3—C4—C5	121.0 (3)	C17—C16A—C15	108.1 (4)
C3—C4—H4A	119.5	C11A—C16A—C15	105.3 (5)
C5—C4—H4A	119.5	C17—C16A—H16A	111.9
C10—C5—C6	117.9 (2)	C11A—C16A—H16A	111.9
C10—C5—C4	122.6 (3)	C15—C16A—H16A	111.9
C6—C5—C4	119.5 (3)	C15—C16B—C11B	105.6 (4)
C7—C6—C1	122.8 (3)	C15—C16B—C17	107.0 (4)
C7—C6—C5	119.4 (3)	C11B—C16B—C17	111.0 (4)
C1—C6—C5	117.8 (3)	C15—C16B—H16B	111.0
C8—C7—C6	121.8 (3)	C11B—C16B—H16B	111.0
C8—C7—H7A	119.1	C17—C16B—H16B	111.0
C6—C7—H7A	119.1	O2—C17—O1	124.7 (3)
C7—C8—C9	118.3 (3)	O2—C17—C16A	141.4 (5)
C7—C8—C11A	105.5 (5)	O1—C17—C16A	93.9 (5)
C9—C8—C11A	136.0 (5)	O2—C17—C16B	108.7 (4)
C7—C8—C11B	132.8 (4)	O1—C17—C16B	126.5 (4)
C9—C8—C11B	108.8 (4)	C16A—C17—C16B	32.9 (3)
C11A—C8—C11B	28.1 (2)	O1—C18—C19	109.2 (5)
C10—C9—C8	121.3 (3)	O1—C18—H18A	109.8
C10—C9—H9A	119.3	C19—C18—H18A	109.8
C8—C9—H9A	119.3	O1—C18—H18B	109.8
C9—C10—C5	121.2 (3)	C19—C18—H18B	109.8
C9—C10—H10A	119.4	H18A—C18—H18B	108.3
C5—C10—H10A	119.4	C18—C19—H19A	109.5
C8—C11A—C16A	108.9 (5)	C18—C19—H19B	109.5
C8—C11A—C12	108.2 (5)	H19A—C19—H19B	109.5
C16A—C11A—C12	110.9 (5)	C18—C19—H19C	109.5
C8—C11A—H11A	109.6	H19A—C19—H19C	109.5
C16A—C11A—H11A	109.6	H19B—C19—H19C	109.5
C12—C11A—H11A	109.6	C21—C20—C13	127.4 (2)
C12—C11B—C16B	109.2 (4)	C21—C20—S1	110.4 (2)
C12—C11B—C8	110.9 (4)	C13—C20—S1	122.1 (2)
C16B—C11B—C8	105.4 (5)	C20—C21—C22	110.3 (3)
C12—C11B—H11B	110.4	C20—C21—H21A	124.9
C16B—C11B—H11B	110.4	C22—C21—H21A	124.9
C8—C11B—H11B	110.4	C23—C22—C21	113.7 (3)
C11B—C12—C13	114.0 (3)	C23—C22—H22A	123.2
C11B—C12—C11A	28.5 (2)	C21—C22—H22A	123.2
C13—C12—C11A	113.0 (3)	C22—C23—S1	113.3 (3)
C11B—C12—H12A	82.6	C22—C23—H23A	123.4
C13—C12—H12A	109.0	S1—C23—H23A	123.4
C11A—C12—H12A	109.0	O3—C24—H24A	109.5
C11B—C12—H12B	129.3	O3—C24—H24B	109.5
C13—C12—H12B	109.0	H24A—C24—H24B	109.5
C11A—C12—H12B	109.0	O3—C24—H24C	109.5
H12A—C12—H12B	107.8	H24A—C24—H24C	109.5
C14—C13—C20	122.8 (2)	H24B—C24—H24C	109.5
C14—C13—C12	120.8 (2)	C23—S1—C20	92.28 (17)
C20—C13—C12	116.4 (2)	C17—O1—C18	115.4 (4)
C13—C14—C15	123.2 (3)	C3—O3—C24	116.9 (3)

C6—C1—C2—C3	0.1 (5)	C13—C14—C15—C16B	−18.7 (5)
C1—C2—C3—C4	−0.1 (5)	C13—C14—C15—C16A	16.4 (6)
C1—C2—C3—O3	−180.0 (3)	C8—C11A—C16A—C17	−68.1 (6)
O3—C3—C4—C5	179.3 (3)	C12—C11A—C16A—C17	172.9 (6)
C2—C3—C4—C5	−0.5 (5)	C8—C11A—C16A—C15	176.9 (6)
C3—C4—C5—C10	−180.0 (3)	C12—C11A—C16A—C15	57.9 (6)
C3—C4—C5—C6	1.1 (4)	O4—C15—C16A—C17	39.2 (7)
C2—C1—C6—C7	−179.8 (3)	C14—C15—C16A—C17	−157.4 (4)
C2—C1—C6—C5	0.5 (4)	C16B—C15—C16A—C17	−70.5 (7)
C10—C5—C6—C7	0.3 (4)	O4—C15—C16A—C11A	153.7 (4)
C4—C5—C6—C7	179.2 (2)	C14—C15—C16A—C11A	−42.9 (6)
C10—C5—C6—C1	179.9 (3)	C16B—C15—C16A—C11A	44.1 (5)
C4—C5—C6—C1	−1.1 (4)	O4—C15—C16B—C11B	−144.5 (4)
C1—C6—C7—C8	179.9 (3)	C14—C15—C16B—C11B	52.6 (5)
C5—C6—C7—C8	−0.4 (4)	C16A—C15—C16B—C11B	−55.9 (5)
C6—C7—C8—C9	0.7 (4)	O4—C15—C16B—C17	−26.2 (7)
C6—C7—C8—C11A	−175.6 (3)	C14—C15—C16B—C17	170.9 (3)
C6—C7—C8—C11B	176.6 (3)	C16A—C15—C16B—C17	62.4 (6)
C7—C8—C9—C10	−0.7 (4)	C12—C11B—C16B—C15	−66.7 (5)
C11A—C8—C9—C10	174.1 (4)	C8—C11B—C16B—C15	174.1 (5)
C11B—C8—C9—C10	−177.6 (3)	C12—C11B—C16B—C17	177.7 (5)
C8—C9—C10—C5	0.6 (5)	C8—C11B—C16B—C17	58.5 (5)
C6—C5—C10—C9	−0.4 (4)	C11A—C16A—C17—O2	−58.3 (7)
C4—C5—C10—C9	−179.3 (3)	C15—C16A—C17—O2	54.8 (8)
C7—C8—C11A—C16A	132.9 (5)	C11A—C16A—C17—O1	123.3 (5)
C9—C8—C11A—C16A	−42.3 (8)	C15—C16A—C17—O1	−123.5 (5)
C11B—C8—C11A—C16A	−59.2 (7)	C11A—C16A—C17—C16B	−48.7 (5)
C7—C8—C11A—C12	−106.5 (5)	C15—C16A—C17—C16B	64.4 (6)
C9—C8—C11A—C12	78.3 (6)	C15—C16B—C17—O2	104.7 (5)
C11B—C8—C11A—C12	61.4 (7)	C11B—C16B—C17—O2	−140.6 (4)
C7—C8—C11B—C12	−60.7 (7)	C15—C16B—C17—O1	−78.9 (5)
C9—C8—C11B—C12	115.5 (5)	C11B—C16B—C17—O1	35.9 (6)
C11A—C8—C11B—C12	−76.8 (8)	C15—C16B—C17—C16A	−69.0 (6)
C7—C8—C11B—C16B	57.3 (5)	C11B—C16B—C17—C16A	45.8 (5)
C9—C8—C11B—C16B	−126.5 (4)	C14—C13—C20—C21	166.3 (3)
C11A—C8—C11B—C16B	41.2 (6)	C12—C13—C20—C21	−15.2 (4)
C16B—C11B—C12—C13	45.4 (6)	C14—C13—C20—S1	−17.2 (3)
C8—C11B—C12—C13	161.1 (4)	C12—C13—C20—S1	161.28 (18)
C16B—C11B—C12—C11A	−49.0 (6)	C13—C20—C21—C22	179.4 (3)
C8—C11B—C12—C11A	66.7 (8)	S1—C20—C21—C22	2.6 (3)
C8—C11A—C12—C11B	−71.9 (8)	C20—C21—C22—C23	−2.8 (5)
C16A—C11A—C12—C11B	47.5 (6)	C21—C22—C23—S1	1.7 (5)
C8—C11A—C12—C13	−170.2 (4)	C22—C23—S1—C20	−0.1 (3)
C16A—C11A—C12—C13	−50.8 (6)	C21—C20—S1—C23	−1.5 (2)
C11B—C12—C13—C14	−9.4 (5)	C13—C20—S1—C23	−178.5 (2)
C11A—C12—C13—C14	21.7 (5)	O2—C17—O1—C18	0.9 (6)
C11B—C12—C13—C20	172.1 (4)	C16A—C17—O1—C18	179.6 (4)
C11A—C12—C13—C20	−156.9 (4)	C16B—C17—O1—C18	−175.0 (4)
C20—C13—C14—C15	173.4 (3)	C19—C18—O1—C17	104.5 (7)
C12—C13—C14—C15	−5.0 (4)	C4—C3—O3—C24	−2.5 (6)
C13—C14—C15—O4	178.6 (3)	C2—C3—O3—C24	177.4 (4)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂O₄S
M_r	406.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.2501 (4), 11.7176 (2), 9.6846 (2)
β (°)	93.048 (1)
V (Å³)	2068.10 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.45 × 0.29 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.922, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	17446, 4035, 2880
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.202, 1.02
No. of reflections	4035
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.38

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

ANM thanks the University of Mysore for research facilities.

References

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