Ethyl 2-(3,4-dimethoxy-benz-yl)-1-phenyl-sulfonyl-1H-indole-3-carboxyl-ate.

In the title compound, C(26)H(25)NO(6)S, the phenyl ring forms a dihedral angle of 82.5 (1)° with the indole ring system. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions and the crystal structure is stabilized by weak inter-molecular C-H⋯O inter-actions.

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 = 479.53

Triclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.03

5046 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.29 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H25NO6S	Z = 2
Mr = 479.53	F(000) = 504
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0563P)2 + 0.284P] where P = (Fo2 + 2Fc2)/3
5046 reflections	(Δ/σ)max < 0.001
310 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .