2-Benzyl-4-(phenyl­sulfon­yl)-1,2,3,4-tetra­hydro­pyrrolo[3,4-b]indole

Kishbaugh, T.L.S.; Gribble, G.W.; Jasinski, J.P.

doi:10.1107/S1600536807032424

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2-Benzyl-4-(phenylsulfonyl)-1,2,3,4-tetrahydropyrrolo[3,4-b]indole

T. L. S. Kishbaugh, G. W. Gribble and J. P. Jasinski

The indole and pyrrolidine ring systems of the title compound, C₂₃H₂₀N₂O₂S, are essentially coplanar. The angle between the planes of the phenylsulfonyl group and the indole ring system is 77.0 (1)°. The benzyl ring and the pyrroloindole plane are nearly perpendicular, with an angle between the planes of 102.0 (1)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032424/fl2138sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032424/fl2138Isup2.hkl Contains datablock I

CCDC reference: 657694

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R factor = 0.040
wR factor = 0.117
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, C₂₃H₂₀N₂O₂S, was synthesized as a precursor to the corresponding pyrrolo[3,4-b]indole as a stable synthetic analogue of indole-2,3-quinodimethane and having a potentially removable benzyl protecting group. The X-ray crystallographic analysis confirms the molecular structure and atom connectivity for (I) that we had proposed for this compound based on NMR spectroscopy and chemical reactions (Kishbaugh & Gribble, 2002).

The pyrrolidine nitrogen N2 has bond angles totaling 336.4 (2)°, indicating slight flattening from a purely pyramidal nitrogen, which is 324° for ammonia with H—N—H bond angles of 108°, and is consistent with the inductive electron-withdrawing properties of a benzyl group.

Related literature top

For the synthesis of the title compound and related chemistry, see: Gribble (2003); Gribble et al. (2005); Roy, Kishbaugh et al. (2007); Roy, Pelkey et al. (2007); Kishbaugh & Gribble (2002); Mohanakrishnan & Srinivasan (1995). For a related structure, see: Kishbaugh et al. (2007).

Experimental top

To a refluxing solution of 2,3-dibromomethyl-1-(phenylsulfonyl)indole (668 mg, 1.51 mmol) (Mohanakrishnan & Srinivasan, 1995) and K₂CO₃ (625 mg, 4.50 mmol) in tetrahydrofuran (20 ml) was added a solution of benzylamine (200 µL, 1.80 mmol) in tetrahydrofuran (20 ml) slowly via addition funnel. After 14 h, the opaque solution was filtered through a Celite pad with ethyl acetate rinses. The combined yellow filtrate was concentrated in vacuo to yield a (I) as a pale yellow solid, which was purified by column chromatography (3:1 hexanes: ethyl acetate) to yield (I) (360 mg) in 61% yield: m.p. 424–425 K. As (I) was unstable toward oxidation, an elemental analysis was not attempted. Recrystallization from hexane–dichloromethane (3:1) yielded crystals that were suitable for X-ray crystallography.

Structure description top

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Figures top

Fig. 1. Molecular structure of (I) showing atom labelling and 50% probability displacement ellipsoids.

2-Benzyl-4-(phenylsulfonyl)-1,2,3,4-tetrahydropyrrolo[3,4-b]indole top

Crystal data top

C₂₃H₂₀N₂O₂S	Z = 2
M_r = 388.47	F(000) = 408
Triclinic, P1	D_x = 1.366 Mg m⁻³
a = 9.178 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 9.6463 (17) Å	Cell parameters from 25 reflections
c = 12.0124 (14) Å	θ = 11.2–19.2°
α = 78.680 (12)°	µ = 0.19 mm⁻¹
β = 110.275 (13)°	T = 296 K
γ = 107.904 (18)°	Prism, colourless
V = 944.5 (3) Å³	0.50 × 0.30 × 0.25 mm

Data collection top

Rigaku AFC-6S diffractometer	2280 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 27.5°, θ_min = 1.8°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.910, T_max = 0.953	l = −15→15
4591 measured reflections	3 standard reflections every 150 reflections
4328 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0326P)² + 0.5372P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
4328 reflections	Δρ_max = 0.28 e Å⁻³
255 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0159 (16)

Crystal data top

C₂₃H₂₀N₂O₂S	γ = 107.904 (18)°
M_r = 388.47	V = 944.5 (3) Å³
Triclinic, P1	Z = 2
a = 9.178 (2) Å	Mo Kα radiation
b = 9.6463 (17) Å	µ = 0.19 mm⁻¹
c = 12.0124 (14) Å	T = 296 K
α = 78.680 (12)°	0.50 × 0.30 × 0.25 mm
β = 110.275 (13)°

Data collection top

Rigaku AFC-6S diffractometer	2280 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.042
T_min = 0.910, T_max = 0.953	3 standard reflections every 150 reflections
4591 measured reflections	intensity decay: none
4328 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 0.99	Δρ_max = 0.28 e Å⁻³
4328 reflections	Δρ_min = −0.31 e Å⁻³
255 parameters

Special details top

Experimental. ¹H (CD₂Cl₂) δ 8.01 (dd, 1H, 1, 8 Hz), 7.85-7.88 (m, 2H), 7.22-7.57 (m, 11H), 4.29 (m, 2H) 4.05 (s, 2H), 3.93 (m, 2H); ¹³C (CD₂Cl₂) (500 MHz) δ 140.2, 139.8, 139.5, 138.4, 134.3, 129.7, 129.3, 129.0, 128.8, 128.7, 128.6, 127.5, 127.0, 126.7, 126.3, 124.03, 124.02, 123.7, 119.6, 114.5, 60.8, 55.1, 53.2; IR (film) λ_max 3055, 2800, 1448, 1369, 1175, 1094, 997, 749, 685 cm^-1; UV (EtOH) λ_max 260 nm.

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
S1	0.22121 (8)	0.47346 (7)	0.12134 (6)	0.03143 (18)
O1	0.0586 (2)	0.4125 (2)	0.12119 (16)	0.0438 (5)
O2	0.2746 (2)	0.4548 (2)	0.02823 (15)	0.0452 (5)
N1	0.3320 (3)	0.3986 (2)	0.24764 (17)	0.0304 (5)
N2	0.1871 (3)	0.2885 (2)	0.50729 (18)	0.0339 (5)
C1	0.1751 (3)	0.3952 (3)	0.4002 (2)	0.0349 (6)
H1	0.2078	0.4952	0.4203	0.042*
H2	0.0674	0.3756	0.3439	0.042*
C2	0.3484 (3)	0.2609 (3)	0.5499 (2)	0.0386 (7)
H3	0.3439	0.1601	0.5832	0.046*
H4	0.4234	0.3258	0.6089	0.046*
C3	0.3927 (3)	0.2933 (3)	0.4369 (2)	0.0322 (6)
C4	0.5080 (3)	0.2795 (3)	0.3867 (2)	0.0314 (6)
C5	0.6387 (3)	0.2191 (3)	0.4284 (3)	0.0421 (7)
H5	0.6660	0.1736	0.5057	0.050*
C6	0.7274 (3)	0.2269 (3)	0.3547 (3)	0.0457 (7)
H6	0.8141	0.1853	0.3823	0.055*
C7	0.6890 (3)	0.2964 (3)	0.2391 (3)	0.0443 (7)
H7	0.7526	0.3025	0.1917	0.053*
C8	0.5592 (3)	0.3563 (3)	0.1935 (2)	0.0360 (6)
H8	0.5330	0.4010	0.1158	0.043*
C9	0.4691 (3)	0.3474 (3)	0.2679 (2)	0.0291 (6)
C10	0.2923 (3)	0.3644 (3)	0.3543 (2)	0.0288 (6)
C11	0.2788 (3)	0.6593 (3)	0.1432 (2)	0.0285 (6)
C12	0.1915 (3)	0.7117 (3)	0.1910 (2)	0.0396 (7)
H9	0.0985	0.6509	0.2063	0.048*
C13	0.2448 (4)	0.8561 (3)	0.2159 (3)	0.0463 (8)
H10	0.1876	0.8929	0.2484	0.056*
C14	0.3820 (4)	0.9452 (3)	0.1928 (3)	0.0492 (8)
H11	0.4173	1.0420	0.2103	0.059*
C15	0.4678 (4)	0.8933 (3)	0.1442 (3)	0.0465 (7)
H12	0.5601	0.9550	0.1285	0.056*
C16	0.4166 (3)	0.7493 (3)	0.1188 (2)	0.0370 (6)
H13	0.4738	0.7133	0.0857	0.044*
C17	0.1417 (3)	0.3296 (3)	0.5993 (2)	0.0369 (6)
H19	0.0399	0.3553	0.5631	0.044*
H20	0.2222	0.4153	0.6329	0.044*
C18	0.1263 (3)	0.2072 (3)	0.6980 (2)	0.0307 (6)
C19	0.1778 (3)	0.2378 (3)	0.8158 (2)	0.0349 (6)
H14	0.2230	0.3343	0.8338	0.042*
C20	0.1631 (3)	0.1271 (3)	0.9067 (2)	0.0427 (7)
H15	0.1973	0.1498	0.9849	0.051*
C21	0.0981 (4)	−0.0168 (3)	0.8823 (3)	0.0460 (7)
H16	0.0902	−0.0915	0.9437	0.055*
C22	0.0445 (3)	−0.0486 (3)	0.7648 (3)	0.0422 (7)
H17	−0.0006	−0.1452	0.7471	0.051*
C23	0.0578 (3)	0.0622 (3)	0.6743 (2)	0.0408 (7)
H18	0.0202	0.0394	0.5959	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0382 (4)	0.0303 (4)	0.0217 (3)	0.0064 (3)	0.0077 (3)	−0.0002 (2)
O1	0.0308 (11)	0.0450 (12)	0.0380 (11)	−0.0015 (9)	0.0027 (8)	0.0027 (9)
O2	0.0691 (14)	0.0461 (12)	0.0249 (10)	0.0171 (11)	0.0175 (10)	−0.0046 (9)
N1	0.0391 (13)	0.0323 (12)	0.0222 (11)	0.0127 (10)	0.0119 (9)	0.0020 (9)
N2	0.0394 (13)	0.0411 (13)	0.0258 (11)	0.0136 (11)	0.0158 (10)	0.0016 (9)
C1	0.0383 (15)	0.0403 (16)	0.0278 (14)	0.0129 (13)	0.0121 (12)	0.0007 (11)
C2	0.0420 (16)	0.0491 (18)	0.0250 (13)	0.0159 (14)	0.0120 (12)	0.0050 (12)
C3	0.0316 (14)	0.0388 (15)	0.0251 (13)	0.0088 (12)	0.0099 (11)	0.0011 (11)
C4	0.0303 (14)	0.0333 (14)	0.0299 (14)	0.0078 (11)	0.0100 (11)	−0.0009 (11)
C5	0.0379 (16)	0.0510 (18)	0.0379 (16)	0.0177 (14)	0.0099 (13)	0.0012 (13)
C6	0.0345 (16)	0.0547 (19)	0.0516 (19)	0.0172 (14)	0.0120 (14)	−0.0067 (15)
C7	0.0403 (17)	0.0516 (19)	0.0522 (19)	0.0088 (14)	0.0268 (15)	−0.0124 (15)
C8	0.0395 (16)	0.0376 (15)	0.0344 (15)	0.0062 (13)	0.0186 (12)	−0.0041 (12)
C9	0.0315 (14)	0.0255 (13)	0.0295 (13)	0.0050 (11)	0.0104 (11)	−0.0031 (10)
C10	0.0316 (14)	0.0334 (14)	0.0220 (12)	0.0078 (11)	0.0108 (11)	−0.0004 (10)
C11	0.0305 (14)	0.0291 (13)	0.0254 (13)	0.0098 (11)	0.0089 (11)	0.0021 (10)
C12	0.0395 (16)	0.0400 (17)	0.0441 (16)	0.0129 (13)	0.0200 (13)	0.0024 (13)
C13	0.0523 (19)	0.0469 (19)	0.0499 (18)	0.0258 (16)	0.0171 (15)	−0.0042 (14)
C14	0.054 (2)	0.0346 (17)	0.0497 (19)	0.0118 (15)	0.0022 (16)	−0.0084 (14)
C15	0.0393 (17)	0.0381 (17)	0.0543 (19)	0.0001 (13)	0.0156 (15)	−0.0009 (14)
C16	0.0359 (16)	0.0387 (16)	0.0386 (15)	0.0082 (13)	0.0169 (13)	−0.0016 (12)
C17	0.0444 (17)	0.0386 (16)	0.0337 (15)	0.0101 (13)	0.0198 (13)	−0.0037 (12)
C18	0.0334 (14)	0.0355 (14)	0.0290 (13)	0.0076 (12)	0.0171 (11)	−0.0047 (11)
C19	0.0355 (15)	0.0353 (15)	0.0353 (15)	0.0031 (12)	0.0152 (12)	−0.0086 (12)
C20	0.0469 (18)	0.0547 (19)	0.0278 (14)	0.0116 (15)	0.0145 (13)	−0.0039 (13)
C21	0.0520 (19)	0.0474 (19)	0.0445 (18)	0.0180 (15)	0.0261 (15)	0.0108 (14)
C22	0.0503 (18)	0.0301 (15)	0.0536 (18)	0.0051 (13)	0.0277 (15)	−0.0073 (13)
C23	0.0529 (18)	0.0373 (16)	0.0352 (15)	0.0037 (14)	0.0200 (14)	−0.0111 (12)

Geometric parameters (Å, º) top

S1—O1	1.4259 (19)	C8—H8	0.9300
S1—O2	1.4271 (19)	C11—C12	1.382 (4)
S1—N1	1.676 (2)	C11—C16	1.386 (3)
S1—C11	1.751 (3)	C12—C13	1.383 (4)
N1—C10	1.402 (3)	C12—H9	0.9300
N1—C9	1.417 (3)	C13—C14	1.372 (4)
N2—C17	1.464 (3)	C13—H10	0.9300
N2—C1	1.476 (3)	C14—C15	1.373 (4)
N2—C2	1.480 (3)	C14—H11	0.9300
C1—C10	1.491 (3)	C15—C16	1.382 (4)
C1—H1	0.9700	C15—H12	0.9300
C1—H2	0.9700	C16—H13	0.9300
C2—C3	1.497 (3)	C17—C18	1.512 (3)
C2—H3	0.9700	C17—H19	0.9700
C2—H4	0.9700	C17—H20	0.9700
C3—C10	1.338 (3)	C18—C23	1.388 (4)
C3—C4	1.436 (3)	C18—C19	1.388 (3)
C4—C5	1.388 (4)	C19—C20	1.380 (4)
C4—C9	1.420 (3)	C19—H14	0.9300
C5—C6	1.373 (4)	C20—C21	1.377 (4)
C5—H5	0.9300	C20—H15	0.9300
C6—C7	1.393 (4)	C21—C22	1.387 (4)
C6—H6	0.9300	C21—H16	0.9300
C7—C8	1.379 (4)	C22—C23	1.376 (4)
C7—H7	0.9300	C22—H17	0.9300
C8—C9	1.389 (3)	C23—H18	0.9300

O1—S1—O2	121.61 (13)	C3—C10—N1	110.5 (2)
O1—S1—N1	105.35 (11)	C3—C10—C1	113.1 (2)
O2—S1—N1	106.06 (11)	N1—C10—C1	136.3 (2)
O1—S1—C11	109.19 (12)	C12—C11—C16	121.1 (2)
O2—S1—C11	109.65 (12)	C12—C11—S1	119.4 (2)
N1—S1—C11	103.31 (11)	C16—C11—S1	119.4 (2)
C10—N1—C9	106.93 (19)	C11—C12—C13	118.9 (3)
C10—N1—S1	123.40 (17)	C11—C12—H9	120.6
C9—N1—S1	129.48 (17)	C13—C12—H9	120.6
C17—N2—C1	113.0 (2)	C14—C13—C12	120.2 (3)
C17—N2—C2	114.1 (2)	C14—C13—H10	119.9
C1—N2—C2	109.32 (19)	C12—C13—H10	119.9
N2—C1—C10	99.3 (2)	C13—C14—C15	120.9 (3)
N2—C1—H1	111.9	C13—C14—H11	119.6
C10—C1—H1	111.9	C15—C14—H11	119.6
N2—C1—H2	111.9	C14—C15—C16	119.9 (3)
C10—C1—H2	111.9	C14—C15—H12	120.1
H1—C1—H2	109.6	C16—C15—H12	120.1
N2—C2—C3	101.5 (2)	C15—C16—C11	119.1 (3)
N2—C2—H3	111.5	C15—C16—H13	120.5
C3—C2—H3	111.5	C11—C16—H13	120.5
N2—C2—H4	111.5	N2—C17—C18	112.0 (2)
C3—C2—H4	111.5	N2—C17—H19	109.2
H3—C2—H4	109.3	C18—C17—H19	109.2
C10—C3—C4	108.6 (2)	N2—C17—H20	109.2
C10—C3—C2	109.0 (2)	C18—C17—H20	109.2
C4—C3—C2	142.4 (2)	H19—C17—H20	107.9
C5—C4—C9	118.7 (2)	C23—C18—C19	117.9 (2)
C5—C4—C3	134.9 (2)	C23—C18—C17	121.6 (2)
C9—C4—C3	106.4 (2)	C19—C18—C17	120.5 (2)
C6—C5—C4	119.7 (3)	C20—C19—C18	121.0 (3)
C6—C5—H5	120.2	C20—C19—H14	119.5
C4—C5—H5	120.2	C18—C19—H14	119.5
C5—C6—C7	120.8 (3)	C21—C20—C19	120.5 (3)
C5—C6—H6	119.6	C21—C20—H15	119.7
C7—C6—H6	119.6	C19—C20—H15	119.7
C8—C7—C6	121.6 (3)	C20—C21—C22	119.0 (3)
C8—C7—H7	119.2	C20—C21—H16	120.5
C6—C7—H7	119.2	C22—C21—H16	120.5
C7—C8—C9	117.5 (3)	C23—C22—C21	120.3 (3)
C7—C8—H8	121.3	C23—C22—H17	119.9
C9—C8—H8	121.3	C21—C22—H17	119.9
C8—C9—N1	130.7 (2)	C22—C23—C18	121.2 (3)
C8—C9—C4	121.8 (2)	C22—C23—H18	119.4
N1—C9—C4	107.5 (2)	C18—C23—H18	119.4

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₂O₂S
M_r	388.47
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.178 (2), 9.6463 (17), 12.0124 (14)
α, β, γ (°)	78.680 (12), 110.275 (13), 107.904 (18)
V (Å³)	944.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.50 × 0.30 × 0.25

Data collection
Diffractometer	Rigaku AFC-6S
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.910, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	4591, 4328, 2280
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.117, 0.99
No. of reflections	4328
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.31

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994), MSC/AFC Diffractometer Control Software, CrystalStructure (Rigaku/MSC, 2005), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), CrystalStructure.

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