2-Azido-methyl-3-methyl-1-phenyl-sulfonyl-1H-indole.

In the title compound, C(16)H(14)N(4)O(2)S, the plane of the indole ring is twisted by 70.4 (2)° with respect to the plane of the azidomethyl- substituent. As a result of the electron-withdrawing character of the phenyl-sulfonyl groups, the N-C bond lengths are slightly longer than the anti-cipated value of approximately 1.355 Å for an N atom with a planar configuration. The indole ring is essentially planar, with a maximum deviation of 0.0296 Å. The azide group is almost linear, the N-N-N angle being 171.4 (3)°. The methyl group on the azide-substituted C atom is in a flagpole position. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 87.07 (10)° with the best plane of the indole moiety. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions, which link the mol-ecules into infinite chains running parallel to the b axis. The crystal packing is further stabilized by C-H⋯π inter-actions.

Related literature

For the biological activity of compounds containing an indole ring system, sulfur and azides, see: Williams et al. (1993 ▶); Amblard et al. (2009 ▶); De-Benedetti et al. (1985 ▶). For related structures, see: Fernandes et al. (2005 ▶). For comparison of mol­ecular dimensions, see: Bassindale (1984 ▶); Allen et al. (1987 ▶).

Experimental

Crystal data

C16H14N4O2S

M = 326.38

Orthorhombic,

a = 11.0337 (4) Å

b = 12.1424 (4) Å

c = 23.2234 (9) Å

V = 3111.37 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 295 K

0.30 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

37510 measured reflections

4231 independent reflections

2776 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.166

S = 0.99

4231 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.35 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030601/rk2287sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030601/rk2287Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030601/rk2287Isup3.cml

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

C16H14N4O2S	F(000) = 1360
Mr = 326.38	Dx = 1.393 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4231 reflections
a = 11.0337 (4) Å	θ = 1.0–29.3°
b = 12.1424 (4) Å	µ = 0.22 mm−1
c = 23.2234 (9) Å	T = 295 K
V = 3111.37 (19) Å3	Block, colourless
Z = 8	0.30 × 0.25 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	2776 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	Rint = 0.049
graphite	θmax = 29.3°, θmin = 2.6°
ω scans	h = −15→13
37510 measured reflections	k = −16→12
4231 independent reflections	l = −31→31

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0987P)2 + 0.4179P] where P = (Fo2 + 2Fc2)/3
4231 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq
C1	0.07440 (17)	0.32220 (15)	0.44968 (8)	0.0419 (4)
C2	−0.0143 (2)	0.25607 (19)	0.47362 (10)	0.0566 (5)
H2	−0.0569	0.2052	0.4516	0.068*
C3	−0.0368 (3)	0.2688 (2)	0.53153 (12)	0.0719 (7)
H3	−0.0958	0.2253	0.5488	0.086*
C4	0.0252 (3)	0.3435 (3)	0.56443 (11)	0.0807 (8)
H4	0.0075	0.3495	0.6034	0.097*
C5	0.1128 (2)	0.4095 (2)	0.54104 (10)	0.0690 (7)
H5	0.1548	0.4600	0.5636	0.083*
C6	0.13730 (18)	0.39903 (16)	0.48237 (9)	0.0478 (5)
C7	0.22068 (19)	0.45506 (16)	0.44500 (9)	0.0513 (5)
C8	0.20845 (16)	0.41425 (15)	0.39159 (8)	0.0424 (4)
C9	0.3091 (3)	0.5412 (2)	0.46516 (13)	0.0844 (9)
H9A	0.3390	0.5816	0.4326	0.127*
H9B	0.3756	0.5062	0.4846	0.127*
H9C	0.2691	0.5908	0.4912	0.127*
C10	0.2829 (2)	0.4427 (2)	0.34045 (9)	0.0529 (5)
H10A	0.3110	0.5181	0.3441	0.064*
H10B	0.2328	0.4382	0.3062	0.064*
C11	−0.08441 (17)	0.36552 (16)	0.33108 (8)	0.0433 (4)
C12	−0.0704 (2)	0.46737 (18)	0.30491 (9)	0.0547 (5)
H12	0.0048	0.4893	0.2910	0.066*
C13	−0.1695 (3)	0.5355 (2)	0.29992 (11)	0.0711 (7)
H13	−0.1615	0.6043	0.2828	0.085*
C14	−0.2791 (3)	0.5020 (3)	0.32010 (13)	0.0801 (9)
H14	−0.3457	0.5484	0.3164	0.096*
C15	−0.2932 (2)	0.4012 (3)	0.34580 (12)	0.0780 (8)
H15	−0.3690	0.3797	0.3592	0.094*
C16	−0.19488 (19)	0.3311 (2)	0.35192 (11)	0.0609 (6)
H16	−0.2033	0.2628	0.3696	0.073*
N1	0.12022 (14)	0.32780 (13)	0.39281 (6)	0.0405 (3)
N2	0.38932 (18)	0.3686 (2)	0.33357 (9)	0.0696 (6)
N3	0.37305 (17)	0.2784 (2)	0.31151 (9)	0.0632 (5)
N4	0.3730 (2)	0.1938 (2)	0.29245 (13)	0.0975 (8)
O1	0.00404 (15)	0.17244 (11)	0.35322 (7)	0.0599 (4)
O2	0.11681 (14)	0.29357 (13)	0.28769 (6)	0.0590 (4)
S1	0.04241 (4)	0.27961 (4)	0.33704 (2)	0.04300 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0427 (10)	0.0382 (9)	0.0449 (10)	−0.0001 (8)	0.0005 (8)	0.0030 (7)
C2	0.0576 (13)	0.0529 (11)	0.0593 (13)	−0.0137 (10)	0.0052 (10)	0.0041 (10)
C3	0.0766 (17)	0.0759 (17)	0.0633 (15)	−0.0133 (13)	0.0191 (13)	0.0112 (12)
C4	0.103 (2)	0.0881 (19)	0.0509 (14)	−0.0151 (17)	0.0197 (14)	−0.0017 (12)
C5	0.0830 (17)	0.0747 (15)	0.0494 (12)	−0.0168 (14)	0.0032 (12)	−0.0107 (11)
C6	0.0500 (11)	0.0466 (11)	0.0468 (10)	−0.0046 (9)	−0.0014 (8)	−0.0035 (8)
C7	0.0491 (11)	0.0467 (11)	0.0580 (12)	−0.0103 (9)	−0.0008 (9)	−0.0061 (9)
C8	0.0363 (9)	0.0417 (9)	0.0490 (10)	−0.0026 (7)	−0.0004 (7)	0.0029 (7)
C9	0.0866 (19)	0.0825 (18)	0.0841 (19)	−0.0432 (16)	0.0045 (15)	−0.0183 (14)
C10	0.0471 (11)	0.0592 (12)	0.0524 (12)	−0.0067 (10)	0.0018 (9)	0.0077 (9)
C11	0.0385 (9)	0.0463 (10)	0.0452 (10)	0.0038 (8)	−0.0076 (8)	−0.0100 (8)
C12	0.0605 (13)	0.0535 (12)	0.0501 (11)	0.0067 (10)	−0.0110 (10)	−0.0028 (9)
C13	0.089 (2)	0.0627 (14)	0.0613 (14)	0.0285 (14)	−0.0205 (13)	−0.0114 (11)
C14	0.0729 (19)	0.089 (2)	0.0786 (18)	0.0410 (16)	−0.0250 (15)	−0.0325 (15)
C15	0.0385 (12)	0.107 (2)	0.0881 (19)	0.0117 (13)	−0.0040 (11)	−0.0294 (16)
C16	0.0414 (11)	0.0694 (15)	0.0719 (14)	0.0003 (10)	−0.0048 (10)	−0.0123 (11)
N1	0.0381 (8)	0.0434 (8)	0.0400 (8)	−0.0047 (6)	−0.0029 (6)	0.0015 (6)
N2	0.0389 (10)	0.0972 (17)	0.0728 (14)	−0.0009 (11)	0.0019 (9)	−0.0075 (11)
N3	0.0461 (10)	0.0842 (17)	0.0594 (12)	0.0081 (11)	0.0006 (9)	0.0063 (11)
N4	0.0768 (17)	0.0868 (18)	0.129 (2)	0.0254 (14)	−0.0104 (16)	−0.0159 (17)
O1	0.0639 (10)	0.0375 (8)	0.0783 (10)	−0.0019 (7)	−0.0153 (8)	−0.0086 (7)
O2	0.0488 (8)	0.0817 (11)	0.0463 (8)	0.0069 (7)	0.0009 (6)	−0.0149 (7)
S1	0.0380 (3)	0.0433 (3)	0.0478 (3)	0.00322 (19)	−0.00599 (19)	−0.00836 (18)

C1—C2	1.383 (3)	C10—H10A	0.9700
C1—C6	1.389 (3)	C10—H10B	0.9700
C1—N1	1.416 (2)	C11—C16	1.377 (3)
C2—C3	1.376 (4)	C11—C12	1.387 (3)
C2—H2	0.9300	C11—S1	1.7509 (19)
C3—C4	1.369 (4)	C12—C13	1.376 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.368 (4)	C13—C14	1.359 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.395 (3)	C14—C15	1.371 (4)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.436 (3)	C15—C16	1.386 (3)
C7—C8	1.342 (3)	C15—H15	0.9300
C7—C9	1.505 (3)	C16—H16	0.9300
C8—N1	1.432 (2)	N1—S1	1.6604 (15)
C8—C10	1.485 (3)	N2—N3	1.222 (3)
C9—H9A	0.9600	N3—N4	1.119 (3)
C9—H9B	0.9600	O1—S1	1.4190 (16)
C9—H9C	0.9600	O2—S1	1.4200 (15)
C10—N2	1.488 (3)
C2—C1—C6	121.61 (19)	C8—C10—H10B	109.1
C2—C1—N1	130.98 (18)	N2—C10—H10B	109.1
C6—C1—N1	107.41 (16)	H10A—C10—H10B	107.9
C3—C2—C1	117.1 (2)	C16—C11—C12	121.6 (2)
C3—C2—H2	121.5	C16—C11—S1	119.92 (17)
C1—C2—H2	121.5	C12—C11—S1	118.48 (16)
C4—C3—C2	122.0 (2)	C13—C12—C11	119.0 (2)
C4—C3—H3	119.0	C13—C12—H12	120.5
C2—C3—H3	119.0	C11—C12—H12	120.5
C5—C4—C3	121.3 (2)	C14—C13—C12	119.9 (3)
C5—C4—H4	119.4	C14—C13—H13	120.0
C3—C4—H4	119.4	C12—C13—H13	120.0
C4—C5—C6	118.1 (2)	C13—C14—C15	121.2 (2)
C4—C5—H5	120.9	C13—C14—H14	119.4
C6—C5—H5	120.9	C15—C14—H14	119.4
C1—C6—C5	119.90 (19)	C14—C15—C16	120.3 (3)
C1—C6—C7	107.95 (17)	C14—C15—H15	119.9
C5—C6—C7	132.2 (2)	C16—C15—H15	119.9
C8—C7—C6	108.61 (17)	C11—C16—C15	118.0 (3)
C8—C7—C9	127.5 (2)	C11—C16—H16	121.0
C6—C7—C9	123.8 (2)	C15—C16—H16	121.0
C7—C8—N1	108.70 (16)	C1—N1—C8	107.24 (14)
C7—C8—C10	126.69 (18)	C1—N1—S1	121.74 (13)
N1—C8—C10	124.23 (17)	C8—N1—S1	126.47 (12)
C7—C9—H9A	109.5	N3—N2—C10	118.10 (19)
C7—C9—H9B	109.5	N4—N3—N2	171.4 (3)
H9A—C9—H9B	109.5	O1—S1—O2	119.71 (10)
C7—C9—H9C	109.5	O1—S1—N1	105.72 (9)
H9A—C9—H9C	109.5	O2—S1—N1	106.78 (9)
H9B—C9—H9C	109.5	O1—S1—C11	109.20 (10)
C8—C10—N2	112.42 (17)	O2—S1—C11	109.09 (9)
C8—C10—H10A	109.1	N1—S1—C11	105.36 (8)
N2—C10—H10A	109.1
C6—C1—C2—C3	−0.7 (3)	C13—C14—C15—C16	0.3 (4)
N1—C1—C2—C3	178.5 (2)	C12—C11—C16—C15	0.3 (3)
C1—C2—C3—C4	0.1 (4)	S1—C11—C16—C15	−179.36 (17)
C2—C3—C4—C5	0.1 (5)	C14—C15—C16—C11	−0.6 (4)
C3—C4—C5—C6	0.2 (4)	C2—C1—N1—C8	177.9 (2)
C2—C1—C6—C5	1.0 (3)	C6—C1—N1—C8	−2.8 (2)
N1—C1—C6—C5	−178.3 (2)	C2—C1—N1—S1	20.4 (3)
C2—C1—C6—C7	−179.01 (19)	C6—C1—N1—S1	−160.34 (14)
N1—C1—C6—C7	1.6 (2)	C7—C8—N1—C1	3.1 (2)
C4—C5—C6—C1	−0.8 (4)	C10—C8—N1—C1	176.49 (18)
C4—C5—C6—C7	179.3 (2)	C7—C8—N1—S1	159.22 (15)
C1—C6—C7—C8	0.3 (2)	C10—C8—N1—S1	−27.4 (3)
C5—C6—C7—C8	−179.7 (2)	C8—C10—N2—N3	80.5 (3)
C1—C6—C7—C9	−177.3 (2)	C1—N1—S1—O1	−48.72 (17)
C5—C6—C7—C9	2.7 (4)	C8—N1—S1—O1	158.31 (15)
C6—C7—C8—N1	−2.1 (2)	C1—N1—S1—O2	−177.23 (14)
C9—C7—C8—N1	175.4 (2)	C8—N1—S1—O2	29.80 (18)
C6—C7—C8—C10	−175.29 (19)	C1—N1—S1—C11	66.85 (16)
C9—C7—C8—C10	2.2 (4)	C8—N1—S1—C11	−86.12 (17)
C7—C8—C10—N2	91.2 (3)	C16—C11—S1—O1	12.21 (19)
N1—C8—C10—N2	−81.0 (2)	C12—C11—S1—O1	−167.48 (15)
C16—C11—C12—C13	0.2 (3)	C16—C11—S1—O2	144.74 (17)
S1—C11—C12—C13	179.90 (16)	C12—C11—S1—O2	−34.96 (17)
C11—C12—C13—C14	−0.5 (3)	C16—C11—S1—N1	−100.94 (17)
C12—C13—C14—C15	0.3 (4)	C12—C11—S1—N1	79.36 (16)

Cg3 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	0.93	2.46	3.322 (3)	154.
C5—H5···Cg3ii	0.93	2.89	3.714 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	0.93	2.46	3.322 (3)	154
C5—H5⋯Cg3ii	0.93	2.89	3.714 (3)	148

Symmetry codes: (i) ; (ii) .