Ethyl 2-(3,4-dimethoxy­benz­yl)-1-phenyl­sulfonyl-1H-indole-3-carboxyl­ate

Gunasekaran, B.; Sureshbabu, R.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809026506

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1856

doi:10.1107/S1600536809026506

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Ethyl 2-(3,4-dimethoxybenzyl)-1-phenylsulfonyl-1H-indole-3-carboxylate

B. Gunasekaran,^a Radhakrishnan Sureshbabu,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 7 July 2009; accepted 7 July 2009; online 15 July 2009)

In the title compound, C₂₆H₂₅NO₆S, the phenyl ring forms a dihedral angle of 82.5 (1)° with the indole ring system. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions and the crystal structure is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For the biological activity of indoles see: Macor et al. (1992 ); Williams et al. (1993 ); For related structures, see: Chakkaravarthi et al. (2007 , 2008 ). For graph set notation see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₆H₂₅NO₆S
M_r = 479.53
Triclinic, $[P \overline 1]$
a = 9.2914 (3) Å
b = 9.3008 (3) Å
c = 14.1561 (5) Å
α = 87.367 (2)°
β = 76.158 (2)°
γ = 87.877 (2)°
V = 1186.13 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 295 K
0.24 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.972
26965 measured reflections
5046 independent reflections
3632 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.124
S = 1.03
5046 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.56	2.911 (3)	103
C8—H8⋯O2	0.93	2.31	2.894 (3)	121
C11—H11⋯O4	0.93	2.36	2.885 (2)	115
C18—H18A⋯O1	0.97	2.23	2.855 (3)	122
C18—H18B⋯O3	0.97	2.33	2.930 (3)	119
C25—H25B⋯O1ⁱ	0.96	2.38	3.231 (3)	147
C9—H9⋯O2ⁱⁱ	0.93	2.58	3.503 (3)	174
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026506/bt2993sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026506/bt2993Isup2.hkl

checkCIF report

Comment top

The chemistry of indole has been of increasing interest, since several compounds of this type possess diverse biological activities (Macor et al., 1992). In addition, phenylsulfonyl indole compounds inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells (Williams et al., 1993).

The geometric parameters of the title compound, (I), (Fig. 1) agree well with the reported similar structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008). The phenyl ring makes a dihedral angle of 82.5 (1)° with the indole ring system. The two aromatic rings C1—C6 and C19—C24 are inclined at an angle of 44.2 (1)° with respect to each other. The sum of the bond angles around N1 [358.8 (5)°] indicate the sp² hybridized state. The torsion angles O1—S1—N1—C14 and O2—S1—N1—C7 [27.8 (2) ° and -37.1 (2) °, respectively] indicate the syn conformation of the sulfonyl moiety.

A distorted tetrahedral geometry [O1—S1—O2 = 120.4 (1) ° and O1—S1—N1 = 106.9 (1) °] around S1 is observed. The widening of the angles may be due to repulsive interactions between the two short S=O bonds.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions. The C6—H6···O1 interaction generate an S(5) graph set motif and C8—H8···O2 and C11—H11···O4 interactions generate S(6) graph set motifs (Bernstein et al., 1995).

Related literature top

For the biological activity of Indoles see: Macor et al. (1992); Williams et al. (1993); For related literature see: Chakkaravarthi et al. (2007, 2008). For graph set notation see: Bernstein et al. (1995).

Experimental top

Ethyl 2-(acetoxymethyl)-1-(phenylsulfonyl)-1H-indole-3-carboxylate (0.39 g, 0.97 mmol) was dissolved in dry 1,2-dichloroethane (15 ml). To this, anhydrous Ferric chloride (0.02 g, 0.09 mmoL) and 1,2-dimethoxy benzene (0.15 ml, 1.16 mmoL) were added under nitrogen atmosphere. It was refluxed for 5 hr and cooled to room temperature. Ferric chloride was carefully filtered off and the filtrate was poured to water (50 ml) and extracted with chloroform (30 ml). The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the product. It was recrystallized from methanol. Yield: 0.28 g (61%), M.Pt: 134–136°C.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Ethyl 2-(3,4-dimethoxybenzyl)-1-phenylsulfonyl-1H-indole-3-carboxylate top

Crystal data top

C₂₆H₂₅NO₆S	Z = 2
M_r = 479.53	F(000) = 504
Triclinic, P1	D_x = 1.343 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2914 (3) Å	Cell parameters from 5120 reflections
b = 9.3008 (3) Å	θ = 2.4–25.1°
c = 14.1561 (5) Å	µ = 0.18 mm⁻¹
α = 87.367 (2)°	T = 295 K
β = 76.158 (2)°	Block, colourless
γ = 87.877 (2)°	0.24 × 0.20 × 0.16 mm
V = 1186.13 (7) Å³

Data collection top

Bruker Kappa APEX2 diffractometer	5046 independent reflections
Radiation source: fine-focus sealed tube	3632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scans	θ_max = 26.8°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.958, T_max = 0.972	k = −11→11
26965 measured reflections	l = −17→17

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) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0563P)² + 0.284P] where P = (F_o² + 2F_c²)/3
5046 reflections	(Δ/σ)_max < 0.001
310 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₆H₂₅NO₆S	γ = 87.877 (2)°
M_r = 479.53	V = 1186.13 (7) Å³
Triclinic, P1	Z = 2
a = 9.2914 (3) Å	Mo Kα radiation
b = 9.3008 (3) Å	µ = 0.18 mm⁻¹
c = 14.1561 (5) Å	T = 295 K
α = 87.367 (2)°	0.24 × 0.20 × 0.16 mm
β = 76.158 (2)°

Data collection top

Bruker Kappa APEX2 diffractometer	5046 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3632 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.972	R_int = 0.025
26965 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
5046 reflections	Δρ_min = −0.29 e Å⁻³
310 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.13534 (6)	−0.05077 (5)	0.22554 (4)	0.06267 (17)
O4	−0.19660 (14)	0.34677 (15)	−0.01641 (10)	0.0687 (4)
N1	0.06324 (16)	0.04353 (16)	0.14286 (11)	0.0546 (4)
O2	0.26358 (17)	−0.12263 (15)	0.17097 (12)	0.0813 (4)
O1	0.01860 (18)	−0.13039 (16)	0.28540 (12)	0.0863 (5)
C12	0.05829 (19)	0.2019 (2)	0.01735 (12)	0.0534 (4)
O5	−0.2124 (3)	0.48992 (18)	0.40802 (13)	0.1186 (7)
O3	−0.34719 (17)	0.2500 (2)	0.11472 (13)	0.1079 (6)
C24	−0.3063 (2)	0.0625 (2)	0.41242 (14)	0.0635 (5)
H24	−0.3268	−0.0350	0.4158	0.076*
C19	−0.24165 (19)	0.12692 (19)	0.32427 (13)	0.0548 (4)
C13	−0.08945 (18)	0.1877 (2)	0.07827 (13)	0.0540 (4)
C1	0.19069 (19)	0.07726 (18)	0.29540 (13)	0.0532 (4)
C14	−0.08487 (18)	0.09319 (19)	0.15310 (13)	0.0536 (4)
C2	0.3292 (2)	0.1354 (2)	0.26491 (14)	0.0611 (5)
H2	0.3928	0.1083	0.2068	0.073*
C20	−0.2098 (2)	0.2712 (2)	0.32182 (13)	0.0633 (5)
H20	−0.1652	0.3168	0.2628	0.076*
C18	−0.2119 (2)	0.0430 (2)	0.23233 (14)	0.0632 (5)
H18A	−0.1932	−0.0572	0.2489	0.076*
H18B	−0.3006	0.0477	0.2075	0.076*
C7	0.15157 (19)	0.11180 (19)	0.05862 (13)	0.0530 (4)
O6	−0.3423 (2)	0.3687 (2)	0.57147 (12)	0.1124 (7)
C8	0.3023 (2)	0.0979 (2)	0.01668 (15)	0.0659 (5)
H8	0.3635	0.0364	0.0443	0.079*
C15	−0.2254 (2)	0.2614 (2)	0.06311 (15)	0.0637 (5)
C10	0.2676 (2)	0.2679 (3)	−0.10809 (15)	0.0771 (6)
H10	0.3086	0.3210	−0.1648	0.092*
C23	−0.3416 (2)	0.1395 (3)	0.49619 (15)	0.0721 (6)
H23	−0.3862	0.0937	0.5552	0.087*
C22	−0.3116 (2)	0.2824 (2)	0.49306 (14)	0.0734 (6)
C3	0.3721 (2)	0.2339 (2)	0.32159 (16)	0.0724 (6)
H3	0.4653	0.2739	0.3019	0.087*
C11	0.1178 (2)	0.2816 (2)	−0.06740 (14)	0.0677 (5)
H11	0.0577	0.3429	−0.0961	0.081*
C6	0.0959 (2)	0.1151 (3)	0.38187 (15)	0.0730 (6)
H6	0.0031	0.0744	0.4024	0.088*
C21	−0.2426 (3)	0.3481 (2)	0.40464 (15)	0.0719 (6)
C9	0.3577 (2)	0.1780 (3)	−0.06701 (16)	0.0741 (6)
H9	0.4584	0.1711	−0.0965	0.089*
C16	−0.3218 (3)	0.4260 (2)	−0.03882 (19)	0.0812 (6)
H16A	−0.3649	0.4908	0.0128	0.097*
H16B	−0.3971	0.3602	−0.0453	0.097*
C5	0.1408 (3)	0.2136 (3)	0.43708 (17)	0.0882 (7)
H5	0.0777	0.2405	0.4955	0.106*
C4	0.2778 (3)	0.2730 (3)	0.40702 (17)	0.0809 (6)
H4	0.3068	0.3404	0.4449	0.097*
C17	−0.2667 (3)	0.5085 (3)	−0.1315 (2)	0.1058 (9)
H17A	−0.1923	0.5732	−0.1241	0.159*
H17B	−0.3475	0.5627	−0.1484	0.159*
H17C	−0.2247	0.4433	−0.1820	0.159*
C25	−0.1090 (5)	0.5491 (3)	0.3324 (2)	0.170 (2)
H25A	−0.0150	0.5004	0.3284	0.255*
H25B	−0.1003	0.6493	0.3430	0.255*
H25C	−0.1390	0.5392	0.2728	0.255*
C26	−0.4361 (4)	0.3220 (4)	0.65636 (19)	0.1280 (12)
H26A	−0.5290	0.2974	0.6437	0.192*
H26B	−0.4524	0.3971	0.7024	0.192*
H26C	−0.3927	0.2388	0.6826	0.192*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0670 (3)	0.0450 (3)	0.0787 (3)	−0.0027 (2)	−0.0224 (2)	−0.0013 (2)
O4	0.0577 (8)	0.0723 (9)	0.0770 (9)	0.0095 (6)	−0.0196 (7)	−0.0045 (7)
N1	0.0505 (8)	0.0554 (8)	0.0594 (9)	−0.0013 (6)	−0.0142 (7)	−0.0106 (7)
O2	0.0858 (10)	0.0559 (8)	0.1053 (12)	0.0212 (7)	−0.0288 (9)	−0.0201 (8)
O1	0.0913 (11)	0.0628 (9)	0.1081 (12)	−0.0266 (8)	−0.0310 (9)	0.0210 (8)
C12	0.0492 (9)	0.0633 (11)	0.0486 (10)	0.0017 (8)	−0.0110 (7)	−0.0180 (8)
O5	0.183 (2)	0.0696 (10)	0.0809 (11)	−0.0411 (12)	0.0196 (12)	−0.0157 (9)
O3	0.0499 (8)	0.1632 (18)	0.0973 (12)	0.0196 (10)	0.0004 (8)	0.0213 (12)
C24	0.0580 (11)	0.0606 (11)	0.0689 (13)	−0.0168 (9)	−0.0097 (9)	0.0126 (10)
C19	0.0467 (9)	0.0563 (10)	0.0592 (11)	−0.0086 (8)	−0.0079 (8)	0.0014 (8)
C13	0.0466 (9)	0.0643 (11)	0.0515 (10)	0.0006 (8)	−0.0106 (7)	−0.0143 (9)
C1	0.0537 (10)	0.0507 (10)	0.0561 (10)	0.0013 (8)	−0.0166 (8)	0.0045 (8)
C14	0.0486 (9)	0.0563 (10)	0.0577 (10)	−0.0051 (8)	−0.0130 (8)	−0.0162 (8)
C2	0.0586 (11)	0.0645 (11)	0.0599 (11)	−0.0039 (9)	−0.0135 (9)	−0.0014 (9)
C20	0.0734 (12)	0.0599 (11)	0.0489 (10)	−0.0141 (9)	0.0015 (9)	0.0043 (8)
C18	0.0546 (10)	0.0623 (11)	0.0725 (12)	−0.0128 (9)	−0.0123 (9)	−0.0068 (9)
C7	0.0496 (9)	0.0565 (10)	0.0540 (10)	−0.0004 (8)	−0.0112 (8)	−0.0185 (8)
O6	0.1424 (17)	0.1171 (14)	0.0607 (10)	−0.0368 (12)	0.0179 (10)	−0.0204 (9)
C8	0.0511 (10)	0.0770 (13)	0.0694 (13)	0.0075 (9)	−0.0123 (9)	−0.0190 (10)
C15	0.0533 (11)	0.0792 (13)	0.0597 (12)	0.0057 (9)	−0.0148 (9)	−0.0144 (10)
C10	0.0677 (13)	0.1025 (17)	0.0533 (11)	−0.0056 (12)	0.0022 (10)	−0.0074 (11)
C23	0.0682 (12)	0.0859 (15)	0.0555 (12)	−0.0210 (11)	−0.0023 (9)	0.0174 (11)
C22	0.0777 (14)	0.0842 (15)	0.0511 (11)	−0.0149 (11)	0.0008 (10)	−0.0037 (10)
C3	0.0688 (13)	0.0759 (13)	0.0768 (14)	−0.0156 (10)	−0.0245 (11)	0.0005 (11)
C11	0.0611 (11)	0.0893 (15)	0.0502 (11)	0.0036 (10)	−0.0086 (9)	−0.0067 (10)
C6	0.0588 (11)	0.0993 (16)	0.0610 (12)	−0.0080 (11)	−0.0135 (9)	−0.0048 (11)
C21	0.0886 (15)	0.0598 (12)	0.0582 (12)	−0.0186 (10)	0.0031 (10)	−0.0015 (9)
C9	0.0508 (10)	0.0985 (16)	0.0684 (13)	0.0021 (11)	−0.0018 (10)	−0.0234 (12)
C16	0.0718 (13)	0.0725 (14)	0.1077 (18)	0.0176 (11)	−0.0386 (13)	−0.0152 (13)
C5	0.0776 (15)	0.124 (2)	0.0647 (13)	0.0054 (14)	−0.0168 (11)	−0.0265 (13)
C4	0.0899 (16)	0.0852 (15)	0.0768 (15)	−0.0024 (13)	−0.0356 (13)	−0.0175 (12)
C17	0.122 (2)	0.0814 (17)	0.124 (2)	0.0123 (16)	−0.0544 (19)	0.0124 (16)
C25	0.293 (5)	0.085 (2)	0.100 (2)	−0.092 (3)	0.029 (3)	0.0008 (17)
C26	0.153 (3)	0.151 (3)	0.0598 (15)	−0.021 (2)	0.0180 (17)	−0.0110 (16)

Geometric parameters (Å, º) top

S1—O1	1.4160 (15)	O6—C26	1.368 (3)
S1—O2	1.4182 (15)	O6—C22	1.368 (3)
S1—N1	1.6809 (16)	C8—C9	1.371 (3)
S1—C1	1.7485 (18)	C8—H8	0.9300
O4—C15	1.326 (2)	C10—C9	1.369 (3)
O4—C16	1.445 (2)	C10—C11	1.377 (3)
N1—C14	1.411 (2)	C10—H10	0.9300
N1—C7	1.414 (2)	C23—C22	1.365 (3)
C12—C11	1.387 (3)	C23—H23	0.9300
C12—C7	1.392 (3)	C22—C21	1.388 (3)
C12—C13	1.443 (2)	C3—C4	1.369 (3)
O5—C21	1.363 (3)	C3—H3	0.9300
O5—C25	1.365 (3)	C11—H11	0.9300
O3—C15	1.196 (2)	C6—C5	1.369 (3)
C24—C19	1.370 (2)	C6—H6	0.9300
C24—C23	1.379 (3)	C9—H9	0.9300
C24—H24	0.9300	C16—C17	1.479 (4)
C19—C20	1.382 (2)	C16—H16A	0.9700
C19—C18	1.511 (3)	C16—H16B	0.9700
C13—C14	1.353 (3)	C5—C4	1.370 (3)
C13—C15	1.471 (3)	C5—H5	0.9300
C1—C6	1.378 (3)	C4—H4	0.9300
C1—C2	1.378 (3)	C17—H17A	0.9600
C14—C18	1.492 (3)	C17—H17B	0.9600
C2—C3	1.375 (3)	C17—H17C	0.9600
C2—H2	0.9300	C25—H25A	0.9600
C20—C21	1.367 (3)	C25—H25B	0.9600
C20—H20	0.9300	C25—H25C	0.9600
C18—H18A	0.9700	C26—H26A	0.9600
C18—H18B	0.9700	C26—H26B	0.9600
C7—C8	1.388 (2)	C26—H26C	0.9600

O1—S1—O2	120.38 (10)	C11—C10—H10	119.2
O1—S1—N1	106.84 (9)	C22—C23—C24	120.41 (18)
O2—S1—N1	105.33 (9)	C22—C23—H23	119.8
O1—S1—C1	108.93 (9)	C24—C23—H23	119.8
O2—S1—C1	108.65 (9)	C23—C22—O6	125.20 (19)
N1—S1—C1	105.74 (8)	C23—C22—C21	118.95 (19)
C15—O4—C16	116.22 (16)	O6—C22—C21	115.85 (19)
C14—N1—C7	108.32 (15)	C4—C3—C2	120.0 (2)
C14—N1—S1	127.51 (13)	C4—C3—H3	120.0
C7—N1—S1	122.95 (12)	C2—C3—H3	120.0
C11—C12—C7	119.17 (17)	C10—C11—C12	118.6 (2)
C11—C12—C13	133.86 (18)	C10—C11—H11	120.7
C7—C12—C13	106.97 (16)	C12—C11—H11	120.7
C21—O5—C25	117.9 (2)	C5—C6—C1	118.8 (2)
C19—C24—C23	121.22 (18)	C5—C6—H6	120.6
C19—C24—H24	119.4	C1—C6—H6	120.6
C23—C24—H24	119.4	O5—C21—C20	124.45 (18)
C24—C19—C20	118.07 (17)	O5—C21—C22	115.43 (18)
C24—C19—C18	120.49 (17)	C20—C21—C22	120.12 (19)
C20—C19—C18	121.41 (16)	C10—C9—C8	121.29 (19)
C14—C13—C12	109.01 (16)	C10—C9—H9	119.4
C14—C13—C15	124.31 (16)	C8—C9—H9	119.4
C12—C13—C15	126.68 (17)	O4—C16—C17	107.4 (2)
C6—C1—C2	121.12 (18)	O4—C16—H16A	110.2
C6—C1—S1	119.04 (15)	C17—C16—H16A	110.2
C2—C1—S1	119.81 (14)	O4—C16—H16B	110.2
C13—C14—N1	108.19 (15)	C17—C16—H16B	110.2
C13—C14—C18	127.54 (17)	H16A—C16—H16B	108.5
N1—C14—C18	124.23 (17)	C6—C5—C4	120.5 (2)
C3—C2—C1	119.09 (19)	C6—C5—H5	119.7
C3—C2—H2	120.5	C4—C5—H5	119.7
C1—C2—H2	120.5	C3—C4—C5	120.4 (2)
C21—C20—C19	121.20 (17)	C3—C4—H4	119.8
C21—C20—H20	119.4	C5—C4—H4	119.8
C19—C20—H20	119.4	C16—C17—H17A	109.5
C14—C18—C19	115.27 (15)	C16—C17—H17B	109.5
C14—C18—H18A	108.5	H17A—C17—H17B	109.5
C19—C18—H18A	108.5	C16—C17—H17C	109.5
C14—C18—H18B	108.5	H17A—C17—H17C	109.5
C19—C18—H18B	108.5	H17B—C17—H17C	109.5
H18A—C18—H18B	107.5	O5—C25—H25A	109.5
C8—C7—C12	121.86 (18)	O5—C25—H25B	109.5
C8—C7—N1	130.62 (18)	H25A—C25—H25B	109.5
C12—C7—N1	107.51 (15)	O5—C25—H25C	109.5
C26—O6—C22	119.5 (2)	H25A—C25—H25C	109.5
C9—C8—C7	117.6 (2)	H25B—C25—H25C	109.5
C9—C8—H8	121.2	O6—C26—H26A	109.5
C7—C8—H8	121.2	O6—C26—H26B	109.5
O3—C15—O4	122.87 (19)	H26A—C26—H26B	109.5
O3—C15—C13	126.1 (2)	O6—C26—H26C	109.5
O4—C15—C13	111.03 (16)	H26A—C26—H26C	109.5
C9—C10—C11	121.5 (2)	H26B—C26—H26C	109.5
C9—C10—H10	119.2

O1—S1—N1—C14	27.85 (17)	C14—N1—C7—C8	−178.86 (17)
O2—S1—N1—C14	156.95 (14)	S1—N1—C7—C8	12.9 (3)
C1—S1—N1—C14	−88.10 (15)	C14—N1—C7—C12	−0.29 (18)
O1—S1—N1—C7	−166.29 (13)	S1—N1—C7—C12	−168.52 (11)
O2—S1—N1—C7	−37.18 (15)	C12—C7—C8—C9	0.8 (3)
C1—S1—N1—C7	77.77 (14)	N1—C7—C8—C9	179.23 (17)
C23—C24—C19—C20	1.3 (3)	C16—O4—C15—O3	−0.6 (3)
C23—C24—C19—C18	−176.42 (18)	C16—O4—C15—C13	−179.67 (16)
C11—C12—C13—C14	179.75 (19)	C14—C13—C15—O3	1.4 (3)
C7—C12—C13—C14	0.14 (19)	C12—C13—C15—O3	−179.1 (2)
C11—C12—C13—C15	0.2 (3)	C14—C13—C15—O4	−179.51 (16)
C7—C12—C13—C15	−179.39 (16)	C12—C13—C15—O4	−0.1 (3)
O1—S1—C1—C6	−19.05 (18)	C19—C24—C23—C22	−0.5 (3)
O2—S1—C1—C6	−151.89 (16)	C24—C23—C22—O6	179.8 (2)
N1—S1—C1—C6	95.47 (16)	C24—C23—C22—C21	−1.2 (3)
O1—S1—C1—C2	159.04 (15)	C26—O6—C22—C23	−14.4 (4)
O2—S1—C1—C2	26.20 (17)	C26—O6—C22—C21	166.6 (3)
N1—S1—C1—C2	−86.45 (16)	C1—C2—C3—C4	0.0 (3)
C12—C13—C14—N1	−0.32 (19)	C9—C10—C11—C12	0.2 (3)
C15—C13—C14—N1	179.22 (16)	C7—C12—C11—C10	0.3 (3)
C12—C13—C14—C18	−178.34 (16)	C13—C12—C11—C10	−179.24 (19)
C15—C13—C14—C18	1.2 (3)	C2—C1—C6—C5	0.9 (3)
C7—N1—C14—C13	0.38 (18)	S1—C1—C6—C5	178.94 (18)
S1—N1—C14—C13	167.92 (12)	C25—O5—C21—C20	−18.9 (5)
C7—N1—C14—C18	178.48 (15)	C25—O5—C21—C22	161.3 (3)
S1—N1—C14—C18	−14.0 (2)	C19—C20—C21—O5	179.0 (2)
C6—C1—C2—C3	−0.7 (3)	C19—C20—C21—C22	−1.2 (3)
S1—C1—C2—C3	−178.79 (15)	C23—C22—C21—O5	−178.2 (2)
C24—C19—C20—C21	−0.5 (3)	O6—C22—C21—O5	0.9 (3)
C18—C19—C20—C21	177.3 (2)	C23—C22—C21—C20	2.0 (4)
C13—C14—C18—C19	−93.4 (2)	O6—C22—C21—C20	−178.9 (2)
N1—C14—C18—C19	88.8 (2)	C11—C10—C9—C8	−0.2 (3)
C24—C19—C18—C14	−152.33 (18)	C7—C8—C9—C10	−0.3 (3)
C20—C19—C18—C14	30.0 (3)	C15—O4—C16—C17	−177.62 (19)
C11—C12—C7—C8	−0.9 (3)	C1—C6—C5—C4	−0.3 (4)
C13—C12—C7—C8	178.82 (16)	C2—C3—C4—C5	0.6 (4)
C11—C12—C7—N1	−179.58 (15)	C6—C5—C4—C3	−0.4 (4)
C13—C12—C7—N1	0.10 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.56	2.911 (3)	103
C8—H8···O2	0.93	2.31	2.894 (3)	121
C11—H11···O4	0.93	2.36	2.885 (2)	115
C18—H18A···O1	0.97	2.23	2.855 (3)	122
C18—H18B···O3	0.97	2.33	2.930 (3)	119
C25—H25B···O1ⁱ	0.96	2.38	3.231 (3)	147
C9—H9···O2ⁱⁱ	0.93	2.58	3.503 (3)	174

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅NO₆S
M_r	479.53
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.2914 (3), 9.3008 (3), 14.1561 (5)
α, β, γ (°)	87.367 (2), 76.158 (2), 87.877 (2)
V (Å³)	1186.13 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Bruker Kappa APEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.958, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	26965, 5046, 3632
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.635

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.124, 1.03
No. of reflections	5046
No. of parameters	310
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.29

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.56	2.911 (3)	103
C8—H8···O2	0.93	2.31	2.894 (3)	121
C11—H11···O4	0.93	2.36	2.885 (2)	115
C18—H18A···O1	0.97	2.23	2.855 (3)	122
C18—H18B···O3	0.97	2.33	2.930 (3)	119
C25—H25B···O1ⁱ	0.96	2.38	3.231 (3)	147
C9—H9···O2ⁱⁱ	0.93	2.58	3.503 (3)	174

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

Acknowledgements

Author thanks AMET University management, India, for their kind support.

References

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