5-Benz-yloxy-3-methyl-1-tosyl-1H-indole.

The title compound, C23H21NO3S, represents one of the few examples of a 5-substituted indole with a toluene-sulfonyl group bonded to the N atom. The benzyl group adopts a synclinal geometry with respect to the indole ring [dihedral angle = 59.95 (4)°], while the tolyl ring is oriented close to perpendicular to the indole ring, making a dihedral angle of 81.85 (3)°. The indole N atom exhibits a slight pyramidalization.

Related literature

For background to physostigmine and related marine natural products, see: Marino et al. (1989 ▶, 1992 ▶). For recent, related structural and synthetic studies, see: Pozza Silveira et al. (2012 ▶); Silveira & Marino (2013 ▶). For related compounds, see: Xiong et al. (2001 ▶); Witulski et al. (2000 ▶). For reference structural data see: Allen et al. (1995 ▶).

Experimental

Crystal data

C23H21NO3S

M = 391.47

Monoclinic,

a = 8.317 (3) Å

b = 15.601 (6) Å

c = 14.752 (5) Å

β = 90.884 (11)°

V = 1914.1 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.39 × 0.33 × 0.15 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.636, T max = 0.746

30660 measured reflections

6415 independent reflections

5550 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.04

6415 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014001/kj2226sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014001/kj2226Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014001/kj2226Isup3.cml

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

C23H21NO3S	Dx = 1.358 Mg m−3
Mr = 391.47	Melting point: 402 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.317 (3) Å	Cell parameters from 9980 reflections
b = 15.601 (6) Å	θ = 2.6–31.6°
c = 14.752 (5) Å	µ = 0.19 mm−1
β = 90.884 (11)°	T = 100 K
V = 1914.1 (12) Å3	Block, colourless
Z = 4	0.39 × 0.33 × 0.15 mm
F(000) = 824

Bruker APEXII diffractometer	6415 independent reflections
Radiation source: fine-focus sealed tube	5550 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.33 pixels mm-1	θmax = 31.6°, θmin = 1.9°
combination of ω and φ–scans	h = −10→12
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −22→22
Tmin = 0.636, Tmax = 0.746	l = −21→21
30660 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.775P] where P = (Fo2 + 2Fc2)/3
6415 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.84082 (10)	0.26302 (5)	0.60391 (6)	0.01478 (15)
O1	0.35145 (9)	0.40007 (6)	0.39442 (5)	0.02043 (16)
S1	0.98068 (3)	0.19050 (2)	0.58368 (2)	0.01438 (6)
O2	1.08199 (9)	0.19022 (5)	0.66274 (5)	0.01998 (15)
C2	0.77142 (12)	0.27143 (6)	0.69017 (6)	0.01592 (17)
H2	0.8203	0.2534	0.7456	0.019*
O3	1.04493 (9)	0.21088 (5)	0.49733 (5)	0.01909 (15)
C3	0.62522 (12)	0.30883 (6)	0.68241 (6)	0.01519 (17)
C3'	0.59545 (12)	0.32359 (6)	0.58690 (6)	0.01410 (17)
C4	0.46627 (12)	0.36208 (7)	0.54150 (6)	0.01652 (18)
H4	0.3777	0.3846	0.5737	0.020*
C5	0.47154 (12)	0.36630 (7)	0.44789 (6)	0.01665 (18)
C6	0.60430 (13)	0.33495 (7)	0.40057 (7)	0.01818 (19)
H6	0.6050	0.3390	0.3363	0.022*
C7	0.73415 (12)	0.29828 (7)	0.44561 (7)	0.01689 (18)
H7	0.8246	0.2777	0.4136	0.020*
C7'	0.72720 (12)	0.29276 (6)	0.53938 (6)	0.01406 (16)
C8	0.51260 (13)	0.33196 (7)	0.75577 (7)	0.0202 (2)
H8A	0.5623	0.3187	0.8148	0.030*
H8B	0.4129	0.2991	0.7484	0.030*
H8C	0.4884	0.3934	0.7525	0.030*
C9	0.21302 (12)	0.42980 (7)	0.44164 (7)	0.01792 (18)
H9A	0.2426	0.4792	0.4806	0.022*
H9B	0.1713	0.3836	0.4808	0.022*
C10	0.08711 (11)	0.45595 (6)	0.37411 (6)	0.01452 (17)
C11	0.02533 (13)	0.53835 (7)	0.37424 (7)	0.01724 (18)
H11	0.0674	0.5795	0.4157	0.021*
C12	−0.09749 (14)	0.56142 (7)	0.31438 (7)	0.0217 (2)
H12	−0.1390	0.6181	0.3148	0.026*
C13	−0.15915 (13)	0.50175 (8)	0.25425 (7)	0.0240 (2)
H13	−0.2447	0.5171	0.2140	0.029*
C14	−0.09673 (13)	0.41950 (8)	0.25233 (7)	0.0222 (2)
H14	−0.1380	0.3788	0.2101	0.027*
C15	0.02576 (13)	0.39676 (7)	0.31194 (7)	0.01826 (18)
H15	0.0685	0.3403	0.3105	0.022*
C16	0.87513 (12)	0.09408 (6)	0.57724 (6)	0.01472 (17)
C17	0.82732 (14)	0.06170 (7)	0.49366 (7)	0.0208 (2)
H17	0.8571	0.0897	0.4392	0.025*
C18	0.73530 (15)	−0.01231 (7)	0.49093 (7)	0.0232 (2)
H18	0.7026	−0.0352	0.4339	0.028*
C19	0.68993 (13)	−0.05376 (7)	0.56976 (7)	0.01902 (19)
C20	0.73877 (14)	−0.01942 (7)	0.65257 (7)	0.0206 (2)
H20	0.7076	−0.0469	0.7070	0.025*
C21	0.83179 (13)	0.05392 (7)	0.65732 (7)	0.01885 (19)
H21	0.8655	0.0765	0.7143	0.023*
C22	0.59305 (15)	−0.13461 (8)	0.56597 (9)	0.0263 (2)
H22A	0.5294	−0.1360	0.5095	0.040*
H22B	0.5209	−0.1366	0.6178	0.040*
H22C	0.6654	−0.1842	0.5681	0.040*

	U11	U22	U33	U12	U13	U23
N1	0.0144 (4)	0.0164 (4)	0.0135 (3)	0.0039 (3)	−0.0007 (3)	0.0004 (3)
O1	0.0149 (3)	0.0329 (4)	0.0135 (3)	0.0072 (3)	−0.0001 (3)	0.0038 (3)
S1	0.01210 (11)	0.01661 (11)	0.01444 (11)	0.00244 (8)	0.00002 (8)	0.00062 (7)
O2	0.0160 (3)	0.0249 (4)	0.0189 (3)	0.0024 (3)	−0.0046 (3)	0.0003 (3)
C2	0.0187 (4)	0.0165 (4)	0.0125 (4)	0.0018 (3)	−0.0011 (3)	0.0009 (3)
O3	0.0167 (3)	0.0226 (3)	0.0180 (3)	0.0019 (3)	0.0042 (3)	0.0027 (3)
C3	0.0174 (4)	0.0165 (4)	0.0116 (4)	0.0017 (3)	−0.0001 (3)	0.0003 (3)
C3'	0.0146 (4)	0.0158 (4)	0.0119 (4)	0.0009 (3)	0.0003 (3)	0.0002 (3)
C4	0.0149 (4)	0.0211 (4)	0.0135 (4)	0.0037 (3)	0.0005 (3)	0.0011 (3)
C5	0.0148 (4)	0.0214 (4)	0.0137 (4)	0.0021 (3)	−0.0011 (3)	0.0027 (3)
C6	0.0172 (4)	0.0249 (5)	0.0124 (4)	0.0024 (4)	0.0010 (3)	0.0021 (3)
C7	0.0154 (4)	0.0219 (4)	0.0135 (4)	0.0027 (3)	0.0021 (3)	0.0011 (3)
C7'	0.0139 (4)	0.0152 (4)	0.0130 (4)	0.0011 (3)	−0.0007 (3)	0.0010 (3)
C8	0.0221 (5)	0.0251 (5)	0.0136 (4)	0.0054 (4)	0.0027 (3)	−0.0001 (3)
C9	0.0151 (4)	0.0245 (5)	0.0142 (4)	0.0038 (4)	0.0000 (3)	0.0008 (3)
C10	0.0123 (4)	0.0173 (4)	0.0140 (4)	0.0002 (3)	0.0002 (3)	0.0024 (3)
C11	0.0183 (5)	0.0173 (4)	0.0161 (4)	0.0017 (3)	0.0008 (3)	−0.0004 (3)
C12	0.0221 (5)	0.0246 (5)	0.0186 (4)	0.0094 (4)	0.0021 (4)	0.0036 (4)
C13	0.0169 (5)	0.0378 (6)	0.0171 (4)	0.0061 (4)	−0.0024 (4)	0.0019 (4)
C14	0.0182 (5)	0.0293 (5)	0.0191 (4)	−0.0035 (4)	−0.0025 (4)	−0.0031 (4)
C15	0.0181 (5)	0.0166 (4)	0.0201 (4)	−0.0013 (3)	−0.0003 (3)	0.0003 (3)
C16	0.0146 (4)	0.0155 (4)	0.0140 (4)	0.0031 (3)	0.0007 (3)	0.0000 (3)
C17	0.0269 (5)	0.0216 (5)	0.0140 (4)	−0.0009 (4)	−0.0005 (4)	0.0006 (3)
C18	0.0292 (6)	0.0226 (5)	0.0178 (4)	−0.0022 (4)	−0.0025 (4)	−0.0025 (4)
C19	0.0169 (4)	0.0171 (4)	0.0231 (5)	0.0021 (3)	0.0019 (4)	−0.0016 (3)
C20	0.0231 (5)	0.0202 (4)	0.0187 (4)	0.0007 (4)	0.0054 (4)	0.0007 (4)
C21	0.0228 (5)	0.0196 (4)	0.0142 (4)	0.0009 (4)	0.0023 (3)	−0.0007 (3)
C22	0.0227 (5)	0.0219 (5)	0.0344 (6)	−0.0032 (4)	0.0025 (4)	−0.0030 (4)

N1—C7'	1.4096 (13)	C17—C18	1.3855 (16)
N1—C2	1.4116 (13)	C18—C19	1.3881 (16)
N1—S1	1.6531 (9)	C19—C20	1.3889 (16)
O1—C5	1.3687 (12)	C19—C22	1.4973 (16)
O1—C9	1.4320 (13)	C20—C21	1.3824 (16)
S1—O3	1.4249 (9)	C2—H2	0.9500
S1—O2	1.4284 (9)	C4—H4	0.9500
S1—C16	1.7436 (11)	C6—H6	0.9500
C2—C3	1.3521 (14)	C7—H7	0.9500
C3—C3'	1.4454 (14)	C8—H8A	0.9800
C3—C8	1.4866 (14)	C8—H8B	0.9800
C3'—C4	1.3933 (14)	C8—H8C	0.9800
C3'—C7'	1.3955 (13)	C9—H9A	0.9900
C4—C5	1.3839 (14)	C9—H9B	0.9900
C5—C6	1.4035 (14)	C11—H11	0.9500
C6—C7	1.3831 (14)	C12—H12	0.9500
C7—C7'	1.3880 (14)	C13—H13	0.9500
C9—C10	1.4912 (14)	C14—H14	0.9500
C10—C11	1.3844 (14)	C15—H15	0.9500
C10—C15	1.3928 (14)	C17—H17	0.9500
C11—C12	1.3874 (15)	C18—H18	0.9500
C12—C13	1.3793 (17)	C20—H20	0.9500
C13—C14	1.3847 (18)	C21—H21	0.9500
C14—C15	1.3818 (15)	C22—H22A	0.9800
C16—C17	1.3852 (14)	C22—H22B	0.9800
C16—C21	1.3897 (14)	C22—H22C	0.9800
C7'—N1—C2	107.40 (8)	C20—C21—C16	118.84 (10)
C7'—N1—S1	124.73 (7)	C3—C2—H2	125.0
C2—N1—S1	121.67 (7)	N1—C2—H2	125.0
C5—O1—C9	115.43 (8)	C5—C4—H4	121.2
O3—S1—O2	120.40 (5)	C3'—C4—H4	121.2
O3—S1—N1	106.46 (5)	C7—C6—H6	119.3
O2—S1—N1	105.22 (5)	C5—C6—H6	119.3
O3—S1—C16	109.83 (5)	C6—C7—H7	121.3
O2—S1—C16	109.39 (5)	C7'—C7—H7	121.3
N1—S1—C16	104.19 (5)	C3—C8—H8A	109.5
C3—C2—N1	110.09 (8)	C3—C8—H8B	109.5
C2—C3—C3'	106.96 (9)	H8A—C8—H8B	109.5
C2—C3—C8	128.25 (9)	C3—C8—H8C	109.5
C3'—C3—C8	124.79 (9)	H8A—C8—H8C	109.5
C4—C3'—C7'	120.85 (9)	H8B—C8—H8C	109.5
C4—C3'—C3	131.03 (9)	O1—C9—H9A	109.9
C7'—C3'—C3	108.11 (9)	C10—C9—H9A	109.9
C5—C4—C3'	117.65 (9)	O1—C9—H9B	109.9
O1—C5—C4	124.01 (9)	C10—C9—H9B	109.9
O1—C5—C6	114.85 (9)	H9A—C9—H9B	108.3
C4—C5—C6	121.14 (9)	C10—C11—H11	119.7
C7—C6—C5	121.30 (9)	C12—C11—H11	119.7
C6—C7—C7'	117.41 (9)	C13—C12—H12	120.1
C7—C7'—C3'	121.62 (9)	C11—C12—H12	120.1
C7—C7'—N1	130.97 (9)	C12—C13—H13	119.9
C3'—C7'—N1	107.32 (8)	C14—C13—H13	119.9
O1—C9—C10	108.98 (8)	C15—C14—H14	120.1
C11—C10—C15	118.98 (9)	C13—C14—H14	120.1
C11—C10—C9	120.67 (9)	C14—C15—H15	119.7
C15—C10—C9	120.32 (9)	C10—C15—H15	119.7
C10—C11—C12	120.64 (10)	C16—C17—H17	120.6
C13—C12—C11	119.80 (10)	C18—C17—H17	120.6
C12—C13—C14	120.18 (10)	C17—C18—H18	119.3
C15—C14—C13	119.86 (10)	C19—C18—H18	119.3
C14—C15—C10	120.52 (10)	C21—C20—H20	119.3
C17—C16—C21	121.18 (10)	C19—C20—H20	119.3
C17—C16—S1	120.03 (8)	C20—C21—H21	120.6
C21—C16—S1	118.66 (8)	C16—C21—H21	120.6
C16—C17—C18	118.73 (10)	C19—C22—H22A	109.5
C17—C18—C19	121.41 (10)	C19—C22—H22B	109.5
C18—C19—C20	118.53 (10)	H22A—C22—H22B	109.5
C18—C19—C22	120.95 (10)	C19—C22—H22C	109.5
C20—C19—C22	120.52 (10)	H22A—C22—H22C	109.5
C21—C20—C19	121.32 (10)	H22B—C22—H22C	109.5
C7'—N1—S1—O3	42.42 (9)	S1—N1—C7'—C7	−27.34 (16)
C2—N1—S1—O3	−168.81 (8)	C2—N1—C7'—C3'	3.62 (11)
C7'—N1—S1—O2	171.26 (8)	S1—N1—C7'—C3'	156.08 (7)
C2—N1—S1—O2	−39.96 (9)	C5—O1—C9—C10	−174.12 (9)
C7'—N1—S1—C16	−73.66 (9)	O1—C9—C10—C11	−122.47 (10)
C2—N1—S1—C16	75.11 (9)	O1—C9—C10—C15	59.84 (12)
C7'—N1—C2—C3	−3.23 (11)	C15—C10—C11—C12	0.98 (15)
S1—N1—C2—C3	−156.71 (8)	C9—C10—C11—C12	−176.74 (10)
N1—C2—C3—C3'	1.52 (11)	C10—C11—C12—C13	0.17 (16)
N1—C2—C3—C8	−178.24 (10)	C11—C12—C13—C14	−1.24 (17)
C2—C3—C3'—C4	−178.08 (11)	C12—C13—C14—C15	1.14 (17)
C8—C3—C3'—C4	1.69 (18)	C13—C14—C15—C10	0.02 (16)
C2—C3—C3'—C7'	0.77 (11)	C11—C10—C15—C14	−1.07 (15)
C8—C3—C3'—C7'	−179.46 (10)	C9—C10—C15—C14	176.66 (10)
C7'—C3'—C4—C5	1.80 (15)	O3—S1—C16—C17	−17.23 (10)
C3—C3'—C4—C5	−179.47 (10)	O2—S1—C16—C17	−151.44 (9)
C9—O1—C5—C4	−1.70 (15)	N1—S1—C16—C17	96.46 (9)
C9—O1—C5—C6	178.08 (9)	O3—S1—C16—C21	166.80 (8)
C3'—C4—C5—O1	178.12 (10)	O2—S1—C16—C21	32.59 (10)
C3'—C4—C5—C6	−1.65 (16)	N1—S1—C16—C21	−79.50 (9)
O1—C5—C6—C7	−179.40 (10)	C21—C16—C17—C18	−0.29 (16)
C4—C5—C6—C7	0.38 (17)	S1—C16—C17—C18	−176.15 (9)
C5—C6—C7—C7'	0.75 (16)	C16—C17—C18—C19	0.40 (17)
C6—C7—C7'—C3'	−0.59 (15)	C17—C18—C19—C20	0.04 (17)
C6—C7—C7'—N1	−176.76 (10)	C17—C18—C19—C22	−178.85 (11)
C4—C3'—C7'—C7	−0.71 (15)	C18—C19—C20—C21	−0.61 (17)
C3—C3'—C7'—C7	−179.70 (9)	C22—C19—C20—C21	178.29 (10)
C4—C3'—C7'—N1	176.26 (9)	C19—C20—C21—C16	0.71 (16)
C3—C3'—C7'—N1	−2.73 (11)	C17—C16—C21—C20	−0.25 (16)
C2—N1—C7'—C7	−179.80 (11)	S1—C16—C21—C20	175.66 (8)