N-[(3RS,4RS)-1-Benzyl-4-methyl­piperidin-3-yl]-5-nitro-1-phenyl­sulfonyl-1H-pyrrolo­[2,3-b]pyridine-4-amine

Pfaffenrot, E.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536812039979

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3051

https://doi.org/10.1107/S1600536812039979

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N-[(3RS,4RS)-1-Benzyl-4-methylpiperidin-3-yl]-5-nitro-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine-4-amine

Ellen Pfaffenrot,^a Dieter Schollmeyer ^b and Stefan Laufer ^a ^*

^aEberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^bInstitute of Organic Chemistry, University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 17 September 2012; accepted 20 September 2012; online 29 September 2012)

The pyrrolopyridine system in the title compound, C₂₇H₂₉N₅O₄S, is oriented at a dihedral angle of 71.20 (5)° towards the phenyl ring of the tosyl residue and at a dihedral angle of 45.43 (4)° towards the benzyl group. The structure shows an intramolecular N—H⋯O and a weak intramolecular N—H⋯N hydrogen bond. The piperidine ring adopts a chair conformation, with the cis substituents displaying a torsion angle of −54.59 (18)°.

Related literature

For inhibitors of Janus kinases, see: Hoffmann-La Roche AG (2011 ).

Experimental

Crystal data

C₂₇H₂₉N₅O₄S
M_r = 519.61
Monoclinic, P 2₁ /c
a = 17.2626 (10) Å
b = 11.5411 (8) Å
c = 13.1313 (9) Å
β = 98.443 (3)°
V = 2587.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 173 K
0.50 × 0.20 × 0.08 mm

Data collection

Bruker APEXII diffractometer
25499 measured reflections
6140 independent reflections
4286 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.117
S = 1.02
6140 reflections
336 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N23—H23⋯O21	0.92	1.95	2.6322 (17)	130
N23—H23⋯N26	0.92	2.35	2.8235 (18)	111

Data collection: APEX2 (Bruker, 2006 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812039979/bt6841sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039979/bt6841Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039979/bt6841Isup3.cml

checkCIF report

Comment top

N-(1-benzyl-4-methylpiperidin-3-yl)-5-nitro-1-tosyl-1H- pyrrolo[2,3-b]pyridine-4-amine is an important intermediate in the synthesis of tricyclic heterocyclic compounds being inhibitors of Janus kinases (Hoffmann-La Roche AG, 2011).

The tosyl residue is oriented in a dihedral angle of 71.2 (0)° towards the pyrrolo-pyridine system and shows a dihedral angle of 45.4 (0)° to the benzyl group (Fig. 1). The methylene group in the title compound presents an angle of 112.0 (5)° between the phenyl and piperidine residue. The equatorial methyl and the axial pyrrolo-pyridine substituent of the piperidine show a torsion angle of 54.5 (9)°. The intramolecular hydrogen bonds N23—H23···O21 1.95 Å and N23—H23···N26 2.35 Å stabilize the molecular conformation (Tabl. 1).

Related literature top

For inhibitors of Janus kinases, see: Hoffmann-La Roche AG (2011).

Experimental top

The compound was prepared by nucleophilic substitution of 4-chloro-5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridine with cis-1-benzyl-3-aminopiperidine in the presence of tertiary amine base. A mixture of 4-chloro-5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (0.624 g, 1.778 mmol), cis-1-benzyl-3-aminopiperidine-dihydrobromide (0.781 g, 2.133 mmol) and diisopropylethylamine (1.9 ml, 10.666 mmol) in 2-propanol (3 ml) was heated in a microwave reactor at 353 K for 1 h. The reaction media was concentrated under vacuum and the product precipitated from methanol to yield 0.855 g (92%) of the title compound. Crystals were obtained by recrystallization in methanol at 277 K.

Structure description top

For inhibitors of Janus kinases, see: Hoffmann-La Roche AG (2011).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level. Hydrogen bonds are represented as dashed lines.

N-[(3RS,4RS)-1-Benzyl-4-methylpiperidin-3-yl]- 5-nitro-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine-4-amine top

Crystal data top

C₂₇H₂₉N₅O₄S	F(000) = 1096
M_r = 519.61	D_x = 1.334 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5909 reflections
a = 17.2626 (10) Å	θ = 2.4–27.4°
b = 11.5411 (8) Å	µ = 0.17 mm⁻¹
c = 13.1313 (9) Å	T = 173 K
β = 98.443 (3)°	Plate, yellow
V = 2587.8 (3) Å³	0.50 × 0.20 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	4286 reflections with I > 2σ(I)
Radiation source: sealed Tube	R_int = 0.035
Graphite monochromator	θ_max = 27.9°, θ_min = 2.1°
CCD scan	h = −22→22
25499 measured reflections	k = −12→15
6140 independent 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0633P)² + 0.2813P] where P = (F_o² + 2F_c²)/3
6140 reflections	(Δ/σ)_max < 0.001
336 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₇H₂₉N₅O₄S	V = 2587.8 (3) Å³
M_r = 519.61	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.2626 (10) Å	µ = 0.17 mm⁻¹
b = 11.5411 (8) Å	T = 173 K
c = 13.1313 (9) Å	0.50 × 0.20 × 0.08 mm
β = 98.443 (3)°

Data collection top

Bruker APEXII diffractometer	4286 reflections with I > 2σ(I)
25499 measured reflections	R_int = 0.035
6140 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	Δρ_max = 0.25 e Å⁻³
6140 reflections	Δρ_min = −0.35 e Å⁻³
336 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
N1	0.25756 (7)	0.38269 (12)	0.13550 (10)	0.0321 (3)
C2	0.30403 (10)	0.38599 (15)	0.05701 (12)	0.0341 (4)
H2	0.2851	0.3892	−0.0146	0.041*
C3	0.37997 (10)	0.38382 (15)	0.09919 (12)	0.0328 (4)
H3	0.4234	0.3859	0.0624	0.039*
C4	0.38439 (9)	0.37788 (13)	0.20968 (11)	0.0261 (3)
C5	0.44591 (8)	0.37411 (12)	0.29571 (11)	0.0249 (3)
C6	0.41701 (9)	0.37441 (13)	0.39271 (11)	0.0257 (3)
C7	0.33663 (9)	0.37230 (14)	0.39967 (12)	0.0303 (3)
H7	0.3220	0.3714	0.4666	0.036*
N8	0.27971 (8)	0.37148 (12)	0.32056 (10)	0.0339 (3)
C9	0.30663 (9)	0.37682 (13)	0.22942 (12)	0.0279 (3)
S10	0.15864 (2)	0.37973 (4)	0.11393 (3)	0.03343 (12)
O11	0.13997 (7)	0.40111 (11)	0.00604 (9)	0.0432 (3)
O12	0.13179 (7)	0.45534 (11)	0.18685 (10)	0.0425 (3)
C13	0.13327 (9)	0.23692 (14)	0.13895 (12)	0.0302 (3)
C14	0.12459 (9)	0.15711 (16)	0.05869 (13)	0.0347 (4)
H14	0.1380	0.1774	−0.0066	0.042*
C15	0.09609 (10)	0.04762 (15)	0.07540 (13)	0.0362 (4)
H15	0.0898	−0.0073	0.0209	0.043*
C16	0.07654 (9)	0.01692 (15)	0.17065 (13)	0.0341 (4)
C17	0.08870 (10)	0.09693 (16)	0.25082 (13)	0.0369 (4)
H17	0.0773	0.0757	0.3169	0.044*
C18	0.11701 (9)	0.20656 (16)	0.23604 (13)	0.0350 (4)
H18	0.1253	0.2604	0.2913	0.042*
C19	0.04180 (12)	−0.10047 (17)	0.18642 (16)	0.0490 (5)
H19A	0.0185	−0.1323	0.1197	0.073*
H19B	0.0013	−0.0927	0.2310	0.073*
H19C	0.0830	−0.1526	0.2188	0.073*
N20	0.46852 (8)	0.37004 (11)	0.48969 (10)	0.0286 (3)
O21	0.54003 (7)	0.35745 (12)	0.49078 (9)	0.0436 (3)
O22	0.44069 (7)	0.37755 (12)	0.57041 (9)	0.0450 (3)
N23	0.52257 (7)	0.37061 (11)	0.28858 (10)	0.0283 (3)
H23	0.5578	0.3611	0.3478	0.034*
C24	0.56077 (9)	0.35130 (14)	0.19766 (12)	0.0283 (3)
H24	0.5213	0.3224	0.1399	0.034*
C25	0.62288 (9)	0.25754 (14)	0.22722 (13)	0.0318 (4)
H25A	0.5979	0.1867	0.2498	0.038*
H25B	0.6486	0.2377	0.1669	0.038*
N26	0.68097 (7)	0.30109 (11)	0.31072 (10)	0.0298 (3)
C27	0.72550 (9)	0.39528 (15)	0.27122 (13)	0.0344 (4)
H27A	0.7483	0.3682	0.2105	0.041*
H27B	0.7688	0.4198	0.3248	0.041*
C28	0.67087 (9)	0.49632 (15)	0.24132 (13)	0.0344 (4)
H28A	0.7001	0.5584	0.2115	0.041*
H28B	0.6528	0.5276	0.3040	0.041*
C29	0.59923 (9)	0.46310 (14)	0.16334 (12)	0.0304 (3)
H29	0.6182	0.4459	0.0966	0.036*
C30	0.54279 (11)	0.56531 (15)	0.14510 (14)	0.0387 (4)
H30A	0.5207	0.5815	0.2082	0.058*
H30B	0.5004	0.5463	0.0894	0.058*
H30C	0.5710	0.6337	0.1259	0.058*
C31	0.73136 (10)	0.20900 (15)	0.36030 (14)	0.0388 (4)
H31A	0.7643	0.1782	0.3108	0.047*
H31B	0.6983	0.1449	0.3795	0.047*
C32	0.78383 (9)	0.25168 (15)	0.45576 (13)	0.0334 (4)
C33	0.75798 (10)	0.33474 (16)	0.51998 (13)	0.0364 (4)
H33	0.7063	0.3645	0.5044	0.044*
C34	0.80684 (11)	0.37471 (16)	0.60677 (13)	0.0378 (4)
H34	0.7887	0.4323	0.6492	0.045*
C35	0.88179 (10)	0.33065 (16)	0.63118 (14)	0.0409 (4)
H35	0.9150	0.3570	0.6908	0.049*
C36	0.90805 (10)	0.24790 (17)	0.56794 (15)	0.0446 (5)
H36	0.9595	0.2174	0.5843	0.054*
C37	0.85963 (10)	0.20925 (16)	0.48089 (15)	0.0401 (4)
H37	0.8785	0.1530	0.4378	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0277 (7)	0.0408 (8)	0.0267 (7)	−0.0019 (6)	−0.0003 (6)	0.0009 (6)
C2	0.0370 (9)	0.0408 (10)	0.0240 (8)	−0.0038 (7)	0.0026 (7)	0.0002 (7)
C3	0.0321 (8)	0.0401 (10)	0.0266 (8)	−0.0028 (7)	0.0053 (7)	−0.0004 (7)
C4	0.0281 (8)	0.0253 (8)	0.0246 (8)	−0.0015 (6)	0.0029 (6)	−0.0010 (6)
C5	0.0271 (8)	0.0212 (7)	0.0261 (8)	−0.0015 (6)	0.0031 (6)	−0.0003 (6)
C6	0.0292 (8)	0.0237 (8)	0.0236 (8)	0.0009 (6)	0.0023 (6)	0.0002 (6)
C7	0.0322 (8)	0.0351 (9)	0.0244 (8)	0.0023 (6)	0.0068 (6)	0.0003 (6)
N8	0.0293 (7)	0.0435 (9)	0.0291 (7)	0.0015 (6)	0.0044 (6)	0.0005 (6)
C9	0.0277 (8)	0.0290 (8)	0.0257 (8)	−0.0007 (6)	−0.0002 (6)	0.0005 (6)
S10	0.0277 (2)	0.0367 (2)	0.0334 (2)	0.00088 (16)	−0.00356 (16)	0.00128 (17)
O11	0.0400 (7)	0.0491 (8)	0.0362 (7)	−0.0019 (5)	−0.0088 (5)	0.0102 (6)
O12	0.0333 (6)	0.0407 (7)	0.0520 (8)	0.0052 (5)	0.0013 (6)	−0.0075 (6)
C13	0.0230 (7)	0.0383 (9)	0.0280 (8)	0.0023 (6)	−0.0000 (6)	−0.0009 (7)
C14	0.0335 (9)	0.0442 (10)	0.0269 (8)	−0.0011 (7)	0.0059 (7)	−0.0008 (7)
C15	0.0361 (9)	0.0387 (10)	0.0341 (9)	0.0031 (7)	0.0061 (7)	−0.0058 (7)
C16	0.0255 (8)	0.0384 (10)	0.0382 (10)	0.0057 (7)	0.0037 (7)	0.0053 (7)
C17	0.0329 (9)	0.0509 (11)	0.0271 (9)	0.0018 (7)	0.0044 (7)	0.0052 (7)
C18	0.0310 (8)	0.0471 (10)	0.0257 (8)	0.0011 (7)	0.0002 (7)	−0.0051 (7)
C19	0.0497 (11)	0.0448 (12)	0.0529 (12)	−0.0017 (9)	0.0094 (9)	0.0082 (9)
N20	0.0339 (7)	0.0263 (7)	0.0251 (7)	−0.0004 (5)	0.0027 (6)	0.0007 (5)
O21	0.0289 (6)	0.0701 (9)	0.0303 (6)	0.0010 (6)	−0.0004 (5)	0.0047 (6)
O22	0.0461 (7)	0.0661 (9)	0.0230 (6)	0.0075 (6)	0.0057 (5)	−0.0026 (6)
N23	0.0244 (6)	0.0367 (8)	0.0235 (7)	−0.0032 (5)	0.0028 (5)	−0.0005 (5)
C24	0.0263 (8)	0.0338 (9)	0.0254 (8)	−0.0031 (6)	0.0054 (6)	−0.0048 (6)
C25	0.0286 (8)	0.0313 (9)	0.0355 (9)	−0.0028 (6)	0.0048 (7)	−0.0061 (7)
N26	0.0254 (6)	0.0303 (7)	0.0331 (7)	−0.0020 (5)	0.0024 (6)	−0.0021 (6)
C27	0.0266 (8)	0.0424 (10)	0.0349 (9)	−0.0085 (7)	0.0066 (7)	−0.0012 (7)
C28	0.0357 (9)	0.0336 (9)	0.0350 (9)	−0.0102 (7)	0.0086 (7)	−0.0011 (7)
C29	0.0332 (8)	0.0337 (9)	0.0252 (8)	−0.0025 (7)	0.0072 (7)	−0.0010 (6)
C30	0.0468 (10)	0.0344 (10)	0.0359 (10)	0.0006 (8)	0.0095 (8)	0.0027 (7)
C31	0.0342 (9)	0.0367 (10)	0.0440 (10)	0.0054 (7)	0.0014 (8)	−0.0058 (8)
C32	0.0311 (8)	0.0334 (9)	0.0358 (9)	0.0017 (7)	0.0051 (7)	0.0041 (7)
C33	0.0315 (8)	0.0428 (10)	0.0347 (9)	0.0042 (7)	0.0043 (7)	0.0028 (8)
C34	0.0443 (10)	0.0403 (10)	0.0295 (9)	−0.0015 (8)	0.0078 (7)	0.0027 (7)
C35	0.0402 (10)	0.0455 (11)	0.0341 (9)	−0.0083 (8)	−0.0037 (8)	0.0096 (8)
C36	0.0310 (9)	0.0505 (12)	0.0500 (11)	0.0037 (8)	−0.0014 (8)	0.0118 (9)
C37	0.0358 (9)	0.0386 (10)	0.0457 (11)	0.0069 (7)	0.0049 (8)	0.0036 (8)

Geometric parameters (Å, º) top

N1—C9	1.3916 (19)	N23—C24	1.4633 (19)
N1—C2	1.396 (2)	N23—H23	0.9205
N1—S10	1.6899 (13)	C24—C25	1.533 (2)
C2—C3	1.346 (2)	C24—C29	1.548 (2)
C2—H2	0.9500	C24—H24	1.0000
C3—C4	1.443 (2)	C25—N26	1.462 (2)
C3—H3	0.9500	C25—H25A	0.9900
C4—C9	1.404 (2)	C25—H25B	0.9900
C4—C5	1.433 (2)	N26—C31	1.464 (2)
C5—N23	1.3409 (19)	N26—C27	1.469 (2)
C5—C6	1.435 (2)	C27—C28	1.515 (2)
C6—C7	1.404 (2)	C27—H27A	0.9900
C6—N20	1.4431 (19)	C27—H27B	0.9900
C7—N8	1.321 (2)	C28—C29	1.534 (2)
C7—H7	0.9500	C28—H28A	0.9900
N8—C9	1.347 (2)	C28—H28B	0.9900
S10—O12	1.4224 (13)	C29—C30	1.526 (2)
S10—O11	1.4276 (12)	C29—H29	1.0000
S10—C13	1.7488 (17)	C30—H30A	0.9800
C13—C18	1.390 (2)	C30—H30B	0.9800
C13—C14	1.391 (2)	C30—H30C	0.9800
C14—C15	1.385 (2)	C31—C32	1.517 (2)
C14—H14	0.9500	C31—H31A	0.9900
C15—C16	1.388 (2)	C31—H31B	0.9900
C15—H15	0.9500	C32—C37	1.391 (2)
C16—C17	1.393 (2)	C32—C33	1.393 (2)
C16—C19	1.508 (3)	C33—C34	1.393 (2)
C17—C18	1.380 (2)	C33—H33	0.9500
C17—H17	0.9500	C34—C35	1.383 (3)
C18—H18	0.9500	C34—H34	0.9500
C19—H19A	0.9800	C35—C36	1.385 (3)
C19—H19B	0.9800	C35—H35	0.9500
C19—H19C	0.9800	C36—C37	1.387 (3)
N20—O22	1.2294 (17)	C36—H36	0.9500
N20—O21	1.2409 (17)	C37—H37	0.9500

C9—N1—C2	108.33 (13)	N23—C24—C29	111.99 (13)
C9—N1—S10	128.04 (11)	C25—C24—C29	110.39 (13)
C2—N1—S10	123.56 (11)	N23—C24—H24	109.3
C3—C2—N1	109.03 (14)	C25—C24—H24	109.3
C3—C2—H2	125.5	C29—C24—H24	109.3
N1—C2—H2	125.5	N26—C25—C24	108.94 (13)
C2—C3—C4	108.60 (14)	N26—C25—H25A	109.9
C2—C3—H3	125.7	C24—C25—H25A	109.9
C4—C3—H3	125.7	N26—C25—H25B	109.9
C9—C4—C5	118.18 (13)	C24—C25—H25B	109.9
C9—C4—C3	105.97 (13)	H25A—C25—H25B	108.3
C5—C4—C3	135.85 (14)	C25—N26—C31	112.41 (13)
N23—C5—C4	124.80 (14)	C25—N26—C27	109.05 (13)
N23—C5—C6	122.51 (13)	C31—N26—C27	112.75 (13)
C4—C5—C6	112.69 (13)	N26—C27—C28	108.85 (13)
C7—C6—C5	122.25 (14)	N26—C27—H27A	109.9
C7—C6—N20	115.39 (13)	C28—C27—H27A	109.9
C5—C6—N20	122.27 (13)	N26—C27—H27B	109.9
N8—C7—C6	125.24 (15)	C28—C27—H27B	109.9
N8—C7—H7	117.4	H27A—C27—H27B	108.3
C6—C7—H7	117.4	C27—C28—C29	113.01 (14)
C7—N8—C9	112.61 (13)	C27—C28—H28A	109.0
N8—C9—N1	123.02 (14)	C29—C28—H28A	109.0
N8—C9—C4	128.92 (14)	C27—C28—H28B	109.0
N1—C9—C4	108.06 (13)	C29—C28—H28B	109.0
O12—S10—O11	120.90 (8)	H28A—C28—H28B	107.8
O12—S10—N1	107.21 (7)	C30—C29—C28	110.19 (14)
O11—S10—N1	103.78 (7)	C30—C29—C24	113.50 (13)
O12—S10—C13	109.66 (8)	C28—C29—C24	110.62 (13)
O11—S10—C13	108.85 (8)	C30—C29—H29	107.4
N1—S10—C13	105.21 (7)	C28—C29—H29	107.4
C18—C13—C14	120.95 (16)	C24—C29—H29	107.4
C18—C13—S10	119.98 (13)	C29—C30—H30A	109.5
C14—C13—S10	118.93 (13)	C29—C30—H30B	109.5
C15—C14—C13	119.02 (16)	H30A—C30—H30B	109.5
C15—C14—H14	120.5	C29—C30—H30C	109.5
C13—C14—H14	120.5	H30A—C30—H30C	109.5
C14—C15—C16	120.97 (16)	H30B—C30—H30C	109.5
C14—C15—H15	119.5	N26—C31—C32	112.05 (14)
C16—C15—H15	119.5	N26—C31—H31A	109.2
C15—C16—C17	118.82 (16)	C32—C31—H31A	109.2
C15—C16—C19	120.47 (16)	N26—C31—H31B	109.2
C17—C16—C19	120.71 (16)	C32—C31—H31B	109.2
C18—C17—C16	121.24 (16)	H31A—C31—H31B	107.9
C18—C17—H17	119.4	C37—C32—C33	118.20 (16)
C16—C17—H17	119.4	C37—C32—C31	120.57 (16)
C17—C18—C13	118.91 (16)	C33—C32—C31	121.22 (14)
C17—C18—H18	120.5	C32—C33—C34	120.92 (16)
C13—C18—H18	120.5	C32—C33—H33	119.5
C16—C19—H19A	109.5	C34—C33—H33	119.5
C16—C19—H19B	109.5	C35—C34—C33	120.08 (17)
H19A—C19—H19B	109.5	C35—C34—H34	120.0
C16—C19—H19C	109.5	C33—C34—H34	120.0
H19A—C19—H19C	109.5	C34—C35—C36	119.47 (17)
H19B—C19—H19C	109.5	C34—C35—H35	120.3
O22—N20—O21	120.82 (13)	C36—C35—H35	120.3
O22—N20—C6	119.35 (13)	C35—C36—C37	120.35 (16)
O21—N20—C6	119.82 (13)	C35—C36—H36	119.8
C5—N23—C24	128.99 (13)	C37—C36—H36	119.8
C5—N23—H23	118.8	C36—C37—C32	120.97 (18)
C24—N23—H23	110.5	C36—C37—H37	119.5
N23—C24—C25	106.45 (13)	C32—C37—H37	119.5

C9—N1—C2—C3	−0.75 (19)	C14—C15—C16—C17	−2.3 (2)
S10—N1—C2—C3	−177.98 (12)	C14—C15—C16—C19	176.94 (16)
N1—C2—C3—C4	0.49 (19)	C15—C16—C17—C18	2.3 (2)
C2—C3—C4—C9	−0.05 (18)	C19—C16—C17—C18	−176.92 (16)
C2—C3—C4—C5	−179.48 (17)	C16—C17—C18—C13	0.2 (2)
C9—C4—C5—N23	177.61 (14)	C14—C13—C18—C17	−2.8 (2)
C3—C4—C5—N23	−3.0 (3)	S10—C13—C18—C17	172.83 (12)
C9—C4—C5—C6	−2.37 (19)	C7—C6—N20—O22	−7.8 (2)
C3—C4—C5—C6	177.00 (17)	C5—C6—N20—O22	175.66 (14)
N23—C5—C6—C7	−176.77 (14)	C7—C6—N20—O21	171.34 (14)
C4—C5—C6—C7	3.2 (2)	C5—C6—N20—O21	−5.2 (2)
N23—C5—C6—N20	−0.5 (2)	C4—C5—N23—C24	−10.8 (2)
C4—C5—C6—N20	179.48 (13)	C6—C5—N23—C24	169.18 (14)
C5—C6—C7—N8	−1.0 (2)	C5—N23—C24—C25	−130.72 (15)
N20—C6—C7—N8	−177.51 (14)	C5—N23—C24—C29	108.55 (17)
C6—C7—N8—C9	−2.1 (2)	N23—C24—C25—N26	−62.82 (15)
C7—N8—C9—N1	−176.84 (14)	C29—C24—C25—N26	58.93 (17)
C7—N8—C9—C4	3.0 (2)	C24—C25—N26—C31	166.21 (13)
C2—N1—C9—N8	−179.41 (15)	C24—C25—N26—C27	−67.99 (16)
S10—N1—C9—N8	−2.3 (2)	C25—N26—C27—C28	65.74 (16)
C2—N1—C9—C4	0.71 (17)	C31—N26—C27—C28	−168.66 (13)
S10—N1—C9—C4	177.77 (11)	N26—C27—C28—C29	−55.95 (18)
C5—C4—C9—N8	−0.7 (2)	C27—C28—C29—C30	174.23 (14)
C3—C4—C9—N8	179.72 (16)	C27—C28—C29—C24	47.91 (18)
C5—C4—C9—N1	179.14 (13)	N23—C24—C29—C30	−54.59 (18)
C3—C4—C9—N1	−0.40 (17)	C25—C24—C29—C30	−173.00 (13)
C9—N1—S10—O12	44.89 (16)	N23—C24—C29—C28	69.86 (16)
C2—N1—S10—O12	−138.45 (14)	C25—C24—C29—C28	−48.55 (17)
C9—N1—S10—O11	173.91 (13)	C25—N26—C31—C32	−172.15 (14)
C2—N1—S10—O11	−9.43 (16)	C27—N26—C31—C32	64.09 (18)
C9—N1—S10—C13	−71.80 (15)	N26—C31—C32—C37	−144.17 (16)
C2—N1—S10—C13	104.86 (14)	N26—C31—C32—C33	35.3 (2)
O12—S10—C13—C18	−21.20 (15)	C37—C32—C33—C34	0.3 (3)
O11—S10—C13—C18	−155.49 (12)	C31—C32—C33—C34	−179.11 (16)
N1—S10—C13—C18	93.81 (13)	C32—C33—C34—C35	−1.0 (3)
O12—S10—C13—C14	154.50 (12)	C33—C34—C35—C36	0.9 (3)
O11—S10—C13—C14	20.22 (15)	C34—C35—C36—C37	−0.1 (3)
N1—S10—C13—C14	−90.49 (13)	C35—C36—C37—C32	−0.6 (3)
C18—C13—C14—C15	2.8 (2)	C33—C32—C37—C36	0.5 (3)
S10—C13—C14—C15	−172.86 (12)	C31—C32—C37—C36	179.90 (16)
C13—C14—C15—C16	−0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N23—H23···O21	0.92	1.95	2.6322 (17)	130
N23—H23···N26	0.92	2.35	2.8235 (18)	111

Experimental details

Crystal data
Chemical formula	C₂₇H₂₉N₅O₄S
M_r	519.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	17.2626 (10), 11.5411 (8), 13.1313 (9)
β (°)	98.443 (3)
V (Å³)	2587.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.50 × 0.20 × 0.08

Data collection
Diffractometer	Bruker APEXII
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	25499, 6140, 4286
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.02
No. of reflections	6140
No. of parameters	336
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.35

Computer programs: APEX2 (Bruker, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N23—H23···O21	0.92	1.95	2.6322 (17)	130
N23—H23···N26	0.92	2.35	2.8235 (18)	111

Acknowledgements

The authors thank Maria Leticia Barbosa, Matthias Gehringer and Peter Keck for suggestions and comments.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hoffmann-La Roche AG (2011). World Patent WO 2011/086053 A1. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

N-[(3RS,4RS)-1-Benzyl-4-methyl­piperidin-3-yl]-5-nitro-1-phenyl­sulfonyl-1H-pyrrolo­[2,3-b]pyridine-4-amine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[(3RS,4RS)-1-Benzyl-4-methylpiperidin-3-yl]-5-nitro-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine-4-amine