Trimethyl 1-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)propane-1,2,3-tricarbox­ylate

Kavitha, T.; Thenmozhi, M.; Sureshbabu, R.; Mohanakrishnan, A.K.; Ponnuswamy, M.N.

doi:10.1107/S1600536808043286

organic compounds

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Volume 65| Part 2| February 2009| Page o264

doi:10.1107/S1600536808043286

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Trimethyl 1-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)propane-1,2,3-tricarboxylate

T. Kavitha,^a M. Thenmozhi,^a Radhakrishnan Sureshbabu,^b A. K. Mohanakrishnan ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, India.
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 17 December 2008; accepted 19 December 2008; online 8 January 2009)

In the title compound, C₂₄H₂₅NO₈S, the indole unit is planar and makes a dihedral angle of 79.73 (11)° with the phenyl ring of the sulfonyl substituent. The molecules in the unit cell are stabilized by C—H⋯O and C—H⋯π intermolecular interactions in addition to van der Waals forces.

Related literature

For the bological activity and applications of indole derivatives, see: Ho et al. (1986 ); Rajeswaran et al. (1999 ); Stevenson et al. (2000 ). For the Thorpe-Ingold effect, see: Bassindale (1984 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₂₅NO₈S
M_r = 487.51
Monoclinic, P 2₁ /c
a = 11.0975 (3) Å
b = 9.8255 (3) Å
c = 22.0027 (6) Å
β = 98.605 (2)°
V = 2372.13 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 (2) K
0.40 × 0.30 × 0.15 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.835, T_max = 0.973
25507 measured reflections
5592 independent reflections
3885 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.135
S = 1.02
5592 reflections
308 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23A⋯O3ⁱ	0.97	2.57	3.476 (3)	156
C13—H13⋯Cg1ⁱⁱ	0.93	2.73	3.633 (3)	163
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z. Cg1 is the centroid of the N1/C2–C5 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, rsb357. DOI: 10.1107/S1600536808043286/bt2840sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043286/bt2840Isup2.hkl

checkCIF report

Comment top

Indole derivatives are used as bioactive drugs (Stevenson et al., 2000) and they exibit anti-allergic, central nervous system depressant and muscle relaxant properties (Ho et al., 1986). Indoles also have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999).

The bond lengths N1- C2 [1.421 (2) Å] and N1- C5 [1.408 (2) Å] are longer than the mean value of 1.355 (1) Å reported for the indole moiety (Allen et al., 1987). The S atom shows a distorted tetrahedral geometry, with O1—S1—O2 [119.99 (11)°] and N1—S1—C10 [105.05 (9)°] angles deviating from ideal tetrahedral values, are attributed to the Thorpe-Ingold effect (Bassindale, 1984). The indole ring is planar and the sulfonyl bound phenyl ring is almost perpendicular to the indole ring system, with a dihedral angle of 79.73 (11)°. The sum of bond angles around N1 (359.5°) indicates that N1 is in sp² hybridization. The ester groups attached to the indole ring system assume extended conformation [C23- C24- O8- C25 = -178.8 (2)°; C20- C21- O6- C22 = -179.2 (2)° and C17- C18- O4- C19 = 177.7 (2)°].

The molecules in the crystal structure extend along the b axis via intermolecular C—H···O hydrogen bonds involving atoms C23 and O3 (-x,y + 1/2,- z + 1/2). Dimerization of the molecules occurs through C—H···π interactions [C13—H13 =0.93, H13···Cg1 = 2.7340, C13···Cg1 = 3.633 (3) Å and C13—H13···Cg1 = 162.73 °, where Cg1 is the centroid of the ring N1—C5].

Related literature top

For the bological activity and applications of indole derivatives, see: Ho et al. (1986); Rajeswaran et al. (1999); Stevenson et al. (2000). For the Thorpe-Ingold effect, see: Bassindale (1984). For bond-length data, see: Allen et al. (1987).Cg1 is the centroid of the N1–C5 ring.

Experimental top

To a stirred solution of dimethyl 2-(2-methyl-1-(phenylsulfonyl)-1H-indol-3-yl) maleate (0.4 g, 0.96 mmol) in dry DMF (1.5 ml), dimethyl acetamide dimethyl acetal (257 mg, 1.9 mmol) was added. Reaction mixture was heated to 110° C for 3hrs under nitrogen atmosphere. Then it was poured to 2% aqueous HCl (15 ml) solution and extracted with CHCl₃. Organic layer was dried over Na₂SO₄ and evaporated. The crude compound was recrystallized from methanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. ORTEP plot of the molecule with displacement ellipsoids drawn at 20% probability level. H atoms have been omitted for clarity.
	Fig. 2. The molecular packing of the compound viewed down the b axis is shown. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

Trimethyl 1-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)propane-1,2,3-tricarboxylate top

Crystal data top

C₂₄H₂₅NO₈S	F(000) = 1024
M_r = 487.51	D_x = 1.365 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5592 reflections
a = 11.0975 (3) Å	θ = 2.3–27.8°
b = 9.8255 (3) Å	µ = 0.19 mm⁻¹
c = 22.0027 (6) Å	T = 293 K
β = 98.605 (2)°	Needle, colourless
V = 2372.13 (12) Å³	0.40 × 0.30 × 0.15 mm
Z = 4

Data collection top

Bruker KAPPA APEXII diffractometer	5592 independent reflections
Radiation source: fine-focus sealed tube	3885 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scan	θ_max = 27.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −14→14
T_min = 0.835, T_max = 0.973	k = −12→12
25507 measured reflections	l = −28→28

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0566P)² + 0.8871P] where P = (F_o² + 2F_c²)/3
5592 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₄H₂₅NO₈S	V = 2372.13 (12) Å³
M_r = 487.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0975 (3) Å	µ = 0.19 mm⁻¹
b = 9.8255 (3) Å	T = 293 K
c = 22.0027 (6) Å	0.40 × 0.30 × 0.15 mm
β = 98.605 (2)°

Data collection top

Bruker KAPPA APEXII diffractometer	5592 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3885 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.973	R_int = 0.027
25507 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	Δρ_max = 0.25 e Å⁻³
5592 reflections	Δρ_min = −0.27 e Å⁻³
308 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
C2	0.20679 (17)	0.1921 (2)	0.08315 (8)	0.0503 (4)
C3	0.19449 (15)	0.11193 (18)	0.13178 (8)	0.0433 (4)
C4	0.29851 (15)	0.13314 (17)	0.17830 (8)	0.0418 (4)
C5	0.37387 (16)	0.22937 (18)	0.15615 (8)	0.0433 (4)
C6	0.48157 (17)	0.2729 (2)	0.19067 (9)	0.0539 (5)
H6	0.5319	0.3352	0.1750	0.065*
C7	0.51138 (19)	0.2207 (2)	0.24880 (10)	0.0604 (5)
H7	0.5826	0.2495	0.2731	0.072*
C8	0.4380 (2)	0.1263 (2)	0.27211 (9)	0.0600 (5)
H8	0.4602	0.0934	0.3118	0.072*
C9	0.33297 (17)	0.0807 (2)	0.23731 (8)	0.0508 (4)
H9	0.2851	0.0154	0.2529	0.061*
C10	0.46121 (19)	0.2643 (2)	0.00851 (9)	0.0540 (5)
C11	0.4134 (3)	0.2268 (3)	−0.04999 (10)	0.0781 (7)
H11	0.3367	0.2565	−0.0680	0.094*
C12	0.4830 (4)	0.1428 (4)	−0.08160 (13)	0.1017 (10)
H12	0.4531	0.1172	−0.1217	0.122*
C13	0.5936 (3)	0.0974 (3)	−0.05521 (16)	0.0975 (9)
H13	0.6381	0.0395	−0.0769	0.117*
C14	0.6397 (3)	0.1361 (3)	0.00258 (16)	0.0978 (9)
H14	0.7161	0.1052	0.0204	0.117*
C15	0.5745 (2)	0.2208 (3)	0.03505 (12)	0.0742 (6)
H15	0.6067	0.2483	0.0746	0.089*
C16	0.1242 (2)	0.2032 (3)	0.02344 (10)	0.0815 (7)
H16A	0.0582	0.1397	0.0228	0.122*
H16B	0.1688	0.1831	−0.0096	0.122*
H16C	0.0921	0.2940	0.0187	0.122*
C17	0.08720 (16)	0.02092 (19)	0.13676 (9)	0.0485 (4)
H17	0.0281	0.0318	0.0993	0.058*
C18	0.12894 (18)	−0.1261 (2)	0.14060 (10)	0.0561 (5)
C19	0.1671 (3)	−0.3195 (3)	0.08387 (17)	0.1092 (11)
H19A	0.1599	−0.3499	0.0420	0.164*
H19B	0.1187	−0.3768	0.1060	0.164*
H19C	0.2508	−0.3241	0.1026	0.164*
C20	0.02316 (16)	0.0556 (2)	0.19188 (9)	0.0493 (4)
H20	0.0750	0.0199	0.2284	0.059*
C21	−0.09641 (18)	−0.0204 (2)	0.18689 (11)	0.0588 (5)
C22	−0.2746 (2)	−0.0409 (3)	0.23308 (17)	0.1057 (11)
H22A	−0.3099	−0.0019	0.2663	0.159*
H22B	−0.2635	−0.1370	0.2397	0.159*
H22C	−0.3278	−0.0257	0.1951	0.159*
C23	0.00794 (17)	0.2075 (2)	0.20302 (9)	0.0510 (4)
H23A	−0.0237	0.2193	0.2415	0.061*
H23B	0.0876	0.2503	0.2076	0.061*
C24	−0.0740 (2)	0.2789 (2)	0.15365 (10)	0.0601 (5)
C25	−0.1514 (3)	0.4926 (3)	0.11907 (15)	0.1146 (12)
H25A	−0.1432	0.5867	0.1308	0.172*
H25B	−0.2346	0.4647	0.1181	0.172*
H25C	−0.1283	0.4809	0.0791	0.172*
N1	0.31622 (14)	0.26844 (17)	0.09733 (7)	0.0501 (4)
O1	0.45912 (16)	0.45716 (15)	0.08815 (7)	0.0753 (5)
O2	0.27957 (16)	0.42841 (17)	0.00952 (7)	0.0764 (5)
O3	0.16646 (16)	−0.18474 (16)	0.18733 (8)	0.0770 (5)
O4	0.12431 (16)	−0.17999 (17)	0.08525 (8)	0.0783 (5)
O5	−0.12856 (16)	−0.1090 (2)	0.15146 (9)	0.0887 (6)
O6	−0.15876 (13)	0.02166 (17)	0.23022 (8)	0.0749 (5)
O7	−0.13414 (19)	0.2252 (2)	0.11119 (9)	0.1051 (7)
O8	−0.07383 (19)	0.41121 (17)	0.16292 (8)	0.0862 (5)
S1	0.37776 (5)	0.37135 (5)	0.04991 (2)	0.05603 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0531 (10)	0.0538 (11)	0.0440 (9)	0.0028 (8)	0.0067 (8)	−0.0011 (8)
C3	0.0434 (9)	0.0440 (9)	0.0427 (9)	0.0047 (7)	0.0073 (7)	−0.0023 (7)
C4	0.0428 (9)	0.0397 (9)	0.0436 (9)	0.0063 (7)	0.0084 (7)	−0.0009 (7)
C5	0.0472 (9)	0.0412 (9)	0.0422 (9)	0.0056 (7)	0.0090 (7)	−0.0009 (7)
C6	0.0508 (10)	0.0504 (11)	0.0605 (11)	−0.0032 (8)	0.0086 (9)	−0.0026 (9)
C7	0.0528 (11)	0.0553 (12)	0.0676 (13)	0.0011 (9)	−0.0090 (9)	−0.0034 (10)
C8	0.0663 (12)	0.0561 (12)	0.0525 (11)	0.0088 (10)	−0.0078 (9)	0.0088 (9)
C9	0.0538 (10)	0.0478 (10)	0.0500 (10)	0.0038 (8)	0.0050 (8)	0.0081 (8)
C10	0.0688 (12)	0.0471 (10)	0.0494 (10)	−0.0065 (9)	0.0200 (9)	0.0035 (8)
C11	0.0970 (18)	0.0868 (18)	0.0511 (12)	0.0039 (14)	0.0131 (11)	−0.0042 (11)
C12	0.131 (3)	0.112 (2)	0.0685 (16)	−0.0052 (19)	0.0349 (17)	−0.0295 (16)
C13	0.108 (2)	0.086 (2)	0.113 (2)	−0.0005 (17)	0.060 (2)	−0.0206 (18)
C14	0.0734 (17)	0.112 (2)	0.115 (2)	0.0110 (16)	0.0366 (17)	−0.009 (2)
C15	0.0618 (13)	0.0907 (18)	0.0722 (14)	−0.0026 (12)	0.0165 (11)	−0.0093 (13)
C16	0.0815 (16)	0.107 (2)	0.0499 (12)	−0.0113 (15)	−0.0089 (11)	0.0143 (13)
C17	0.0444 (9)	0.0502 (10)	0.0501 (10)	0.0013 (8)	0.0050 (8)	−0.0035 (8)
C18	0.0487 (10)	0.0503 (11)	0.0705 (13)	−0.0022 (9)	0.0124 (9)	−0.0050 (10)
C19	0.117 (2)	0.0646 (17)	0.148 (3)	0.0101 (16)	0.027 (2)	−0.0415 (19)
C20	0.0422 (9)	0.0526 (11)	0.0536 (10)	0.0018 (8)	0.0085 (8)	0.0017 (8)
C21	0.0488 (10)	0.0526 (12)	0.0760 (14)	0.0018 (9)	0.0121 (10)	0.0042 (11)
C22	0.0609 (14)	0.092 (2)	0.175 (3)	−0.0002 (14)	0.0522 (18)	0.017 (2)
C23	0.0485 (10)	0.0534 (11)	0.0521 (10)	−0.0001 (8)	0.0107 (8)	−0.0055 (9)
C24	0.0615 (12)	0.0592 (13)	0.0586 (12)	0.0057 (10)	0.0053 (10)	−0.0031 (10)
C25	0.156 (3)	0.079 (2)	0.099 (2)	0.031 (2)	−0.010 (2)	0.0267 (17)
N1	0.0567 (9)	0.0531 (9)	0.0413 (8)	−0.0020 (7)	0.0102 (7)	0.0041 (7)
O1	0.1135 (13)	0.0496 (9)	0.0662 (9)	−0.0231 (8)	0.0248 (9)	−0.0078 (7)
O2	0.0989 (12)	0.0637 (10)	0.0682 (9)	0.0233 (9)	0.0176 (9)	0.0220 (8)
O3	0.0903 (12)	0.0548 (9)	0.0878 (11)	0.0109 (8)	0.0190 (9)	0.0118 (9)
O4	0.0842 (11)	0.0650 (10)	0.0850 (11)	0.0087 (8)	0.0105 (9)	−0.0285 (9)
O5	0.0715 (10)	0.0827 (12)	0.1152 (14)	−0.0247 (9)	0.0244 (10)	−0.0281 (11)
O6	0.0568 (8)	0.0733 (10)	0.1017 (12)	−0.0007 (7)	0.0357 (8)	−0.0018 (9)
O7	0.1096 (15)	0.0845 (13)	0.1019 (14)	0.0232 (11)	−0.0467 (12)	−0.0187 (11)
O8	0.1247 (15)	0.0551 (9)	0.0718 (10)	0.0118 (10)	−0.0082 (10)	0.0064 (8)
S1	0.0792 (4)	0.0419 (3)	0.0498 (3)	0.0007 (2)	0.0190 (2)	0.0046 (2)

Geometric parameters (Å, º) top

C2—C3	1.352 (3)	C17—C18	1.516 (3)
C2—N1	1.421 (2)	C17—C20	1.533 (3)
C2—C16	1.489 (3)	C17—H17	0.9800
C3—C4	1.439 (2)	C18—O3	1.198 (3)
C3—C17	1.506 (3)	C18—O4	1.322 (3)
C4—C9	1.396 (2)	C19—O4	1.452 (3)
C4—C5	1.397 (2)	C19—H19A	0.9600
C5—C6	1.384 (3)	C19—H19B	0.9600
C5—N1	1.408 (2)	C19—H19C	0.9600
C6—C7	1.372 (3)	C20—C21	1.512 (3)
C6—H6	0.9300	C20—C23	1.526 (3)
C7—C8	1.382 (3)	C20—H20	0.9800
C7—H7	0.9300	C21—O5	1.187 (3)
C8—C9	1.371 (3)	C21—O6	1.325 (3)
C8—H8	0.9300	C22—O6	1.434 (3)
C9—H9	0.9300	C22—H22A	0.9600
C10—C11	1.368 (3)	C22—H22B	0.9600
C10—C15	1.373 (3)	C22—H22C	0.9600
C10—S1	1.745 (2)	C23—C24	1.484 (3)
C11—C12	1.386 (4)	C23—H23A	0.9700
C11—H11	0.9300	C23—H23B	0.9700
C12—C13	1.353 (4)	C24—O7	1.188 (3)
C12—H12	0.9300	C24—O8	1.316 (3)
C13—C14	1.352 (4)	C25—O8	1.436 (3)
C13—H13	0.9300	C25—H25A	0.9600
C14—C15	1.371 (4)	C25—H25B	0.9600
C14—H14	0.9300	C25—H25C	0.9600
C15—H15	0.9300	N1—S1	1.6706 (16)
C16—H16A	0.9600	O1—S1	1.4165 (16)
C16—H16B	0.9600	O2—S1	1.4148 (16)
C16—H16C	0.9600

C3—C2—N1	108.53 (16)	C20—C17—H17	108.1
C3—C2—C16	128.23 (19)	O3—C18—O4	124.0 (2)
N1—C2—C16	123.25 (18)	O3—C18—C17	124.8 (2)
C2—C3—C4	108.26 (16)	O4—C18—C17	111.16 (19)
C2—C3—C17	125.32 (16)	O4—C19—H19A	109.5
C4—C3—C17	126.38 (16)	O4—C19—H19B	109.5
C9—C4—C5	118.63 (16)	H19A—C19—H19B	109.5
C9—C4—C3	133.41 (17)	O4—C19—H19C	109.5
C5—C4—C3	107.95 (15)	H19A—C19—H19C	109.5
C6—C5—C4	122.01 (17)	H19B—C19—H19C	109.5
C6—C5—N1	131.02 (17)	C21—C20—C23	112.17 (16)
C4—C5—N1	106.95 (15)	C21—C20—C17	109.78 (16)
C7—C6—C5	117.66 (19)	C23—C20—C17	114.83 (16)
C7—C6—H6	121.2	C21—C20—H20	106.5
C5—C6—H6	121.2	C23—C20—H20	106.5
C6—C7—C8	121.56 (19)	C17—C20—H20	106.5
C6—C7—H7	119.2	O5—C21—O6	124.3 (2)
C8—C7—H7	119.2	O5—C21—C20	125.7 (2)
C9—C8—C7	120.73 (18)	O6—C21—C20	109.94 (19)
C9—C8—H8	119.6	O6—C22—H22A	109.5
C7—C8—H8	119.6	O6—C22—H22B	109.5
C8—C9—C4	119.37 (18)	H22A—C22—H22B	109.5
C8—C9—H9	120.3	O6—C22—H22C	109.5
C4—C9—H9	120.3	H22A—C22—H22C	109.5
C11—C10—C15	121.2 (2)	H22B—C22—H22C	109.5
C11—C10—S1	119.50 (18)	C24—C23—C20	114.51 (17)
C15—C10—S1	119.32 (17)	C24—C23—H23A	108.6
C10—C11—C12	117.8 (3)	C20—C23—H23A	108.6
C10—C11—H11	121.1	C24—C23—H23B	108.6
C12—C11—H11	121.1	C20—C23—H23B	108.6
C13—C12—C11	121.3 (3)	H23A—C23—H23B	107.6
C13—C12—H12	119.4	O7—C24—O8	123.3 (2)
C11—C12—H12	119.4	O7—C24—C23	125.2 (2)
C14—C13—C12	120.2 (3)	O8—C24—C23	111.51 (18)
C14—C13—H13	119.9	O8—C25—H25A	109.5
C12—C13—H13	119.9	O8—C25—H25B	109.5
C13—C14—C15	120.4 (3)	H25A—C25—H25B	109.5
C13—C14—H14	119.8	O8—C25—H25C	109.5
C15—C14—H14	119.8	H25A—C25—H25C	109.5
C14—C15—C10	119.2 (3)	H25B—C25—H25C	109.5
C14—C15—H15	120.4	C5—N1—C2	108.28 (15)
C10—C15—H15	120.4	C5—N1—S1	124.53 (13)
C2—C16—H16A	109.5	C2—N1—S1	126.71 (13)
C2—C16—H16B	109.5	C18—O4—C19	115.4 (2)
H16A—C16—H16B	109.5	C21—O6—C22	117.8 (2)
C2—C16—H16C	109.5	C24—O8—C25	117.3 (2)
H16A—C16—H16C	109.5	O2—S1—O1	119.99 (11)
H16B—C16—H16C	109.5	O2—S1—N1	106.49 (9)
C3—C17—C18	109.37 (15)	O1—S1—N1	105.85 (8)
C3—C17—C20	113.00 (15)	O2—S1—C10	109.26 (10)
C18—C17—C20	109.98 (16)	O1—S1—C10	109.13 (10)
C3—C17—H17	108.1	N1—S1—C10	105.05 (9)
C18—C17—H17	108.1

N1—C2—C3—C4	−1.3 (2)	C3—C17—C20—C23	41.5 (2)
C16—C2—C3—C4	178.3 (2)	C18—C17—C20—C23	164.05 (16)
N1—C2—C3—C17	176.42 (16)	C23—C20—C21—O5	139.6 (2)
C16—C2—C3—C17	−4.0 (3)	C17—C20—C21—O5	10.7 (3)
C2—C3—C4—C9	178.73 (19)	C23—C20—C21—O6	−43.5 (2)
C17—C3—C4—C9	1.1 (3)	C17—C20—C21—O6	−172.46 (17)
C2—C3—C4—C5	0.2 (2)	C21—C20—C23—C24	−60.8 (2)
C17—C3—C4—C5	−177.43 (16)	C17—C20—C23—C24	65.5 (2)
C9—C4—C5—C6	0.6 (3)	C20—C23—C24—O7	7.2 (3)
C3—C4—C5—C6	179.38 (16)	C20—C23—C24—O8	−173.73 (18)
C9—C4—C5—N1	−177.85 (15)	C6—C5—N1—C2	−179.95 (19)
C3—C4—C5—N1	0.92 (19)	C4—C5—N1—C2	−1.68 (19)
C4—C5—C6—C7	−1.6 (3)	C6—C5—N1—S1	7.5 (3)
N1—C5—C6—C7	176.41 (19)	C4—C5—N1—S1	−174.21 (12)
C5—C6—C7—C8	1.0 (3)	C3—C2—N1—C5	1.8 (2)
C6—C7—C8—C9	0.6 (3)	C16—C2—N1—C5	−177.8 (2)
C7—C8—C9—C4	−1.7 (3)	C3—C2—N1—S1	174.17 (14)
C5—C4—C9—C8	1.1 (3)	C16—C2—N1—S1	−5.4 (3)
C3—C4—C9—C8	−177.31 (19)	O3—C18—O4—C19	0.8 (3)
C15—C10—C11—C12	0.2 (4)	C17—C18—O4—C19	177.7 (2)
S1—C10—C11—C12	179.3 (2)	O5—C21—O6—C22	−2.2 (4)
C10—C11—C12—C13	1.1 (5)	C20—C21—O6—C22	−179.2 (2)
C11—C12—C13—C14	−1.5 (5)	O7—C24—O8—C25	0.3 (4)
C12—C13—C14—C15	0.5 (5)	C23—C24—O8—C25	−178.8 (2)
C13—C14—C15—C10	0.8 (5)	C5—N1—S1—O2	−156.71 (15)
C11—C10—C15—C14	−1.2 (4)	C2—N1—S1—O2	32.14 (19)
S1—C10—C15—C14	179.7 (2)	C5—N1—S1—O1	−27.97 (18)
C2—C3—C17—C18	116.4 (2)	C2—N1—S1—O1	160.89 (16)
C4—C3—C17—C18	−66.4 (2)	C5—N1—S1—C10	87.45 (16)
C2—C3—C17—C20	−120.8 (2)	C2—N1—S1—C10	−83.70 (18)
C4—C3—C17—C20	56.5 (2)	C11—C10—S1—O2	−13.0 (2)
C3—C17—C18—O3	88.7 (2)	C15—C10—S1—O2	166.18 (18)
C20—C17—C18—O3	−36.0 (3)	C11—C10—S1—O1	−145.95 (18)
C3—C17—C18—O4	−88.3 (2)	C15—C10—S1—O1	33.2 (2)
C20—C17—C18—O4	147.10 (17)	C11—C10—S1—N1	100.93 (19)
C3—C17—C20—C21	169.00 (15)	C15—C10—S1—N1	−79.91 (19)
C18—C17—C20—C21	−68.48 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23A···O3ⁱ	0.97	2.57	3.476 (3)	156
C13—H13···Cg1ⁱⁱ	0.93	2.73	3.633 (3)	163

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₅NO₈S
M_r	487.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.0975 (3), 9.8255 (3), 22.0027 (6)
β (°)	98.605 (2)
V (Å³)	2372.13 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.40 × 0.30 × 0.15

Data collection
Diffractometer	Bruker KAPPA APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.835, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	25507, 5592, 3885
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.656

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.135, 1.02
No. of reflections	5592
No. of parameters	308
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), ORTEP (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23A···O3ⁱ	0.97	2.57	3.476 (3)	155.8
C13—H13···Cg1ⁱⁱ	0.93	2.73	3.633 (3)	162.7

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

Acknowledgements

TK thanks Dr Babu Varghese, SAIF, IIT–Madras, Chennai, India, for his help with the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons. Google Scholar
Bruker (2004). SAINT and APEX2 . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ho, C. Y., Haegman, W. E. & Perisco, F. (1986). J. Med. Chem. 29, 118–121. Google Scholar
Rajeswaran, W. G., Labroo, R. B., Cohen, L. A. & King, M. M. (1999). J. Org. Chem. 64, 1369–1371. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stevenson, G. I., Smith, A. L., Lewis, S. G., Neduvelil, J. G., Patel, S., Marwood, R. & Castro, J. L. (2000). Bioorg. Med. Chem. Lett. 10, 2697–2704. Web of Science CrossRef PubMed CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Tri­methyl 1-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)propane-1,2,3-tricarbox­ylate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Trimethyl 1-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)propane-1,2,3-tricarboxylate