Phen-yl(3-methyl-1-phenyl-sulfonyl-1H-indol-2-yl)methanone.

In the title compound, C(22)H(17)NO(3)S, the N atom of the indole ring system deviates by 0.031 (3) Å from a least-squares plane fitted through all nine non-H ring atoms. The geometry around the S atom can be described as distorted tetra-hedral. As a result of the electron-withdrawing character of the phenyl-sulfonyl groups, the N-Csp(2) bond lengths are longer than the typical mean value for N atoms with a planar configuration.

Related literature

For background to the biological activity of indole-containing compounds, see: Ma et al. (2001 ▶). For a related structure, see: Ranjith et al. (2011 ▶). For discussion of bond angles around n class="Disease">N atoms, see: Beddoes et al. (1986 ▶).

Experimental

Crystal data

C22H17NO3S

M = 375.43

Monoclinic,

a = 22.8120 (7) Å

b = 10.5199 (4) Å

c = 16.1346 (6) Å

β = 103.926 (1)°

V = 3758.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.953, T max = 0.964

24166 measured reflections

5682 independent reflections

3487 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.145

S = 1.02

5682 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014826/nk2097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014826/nk2097Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811014826/nk2097Isup3.cml

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

C22H17NO3S	F(000) = 1568
Mr = 375.43	Dx = 1.327 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5682 reflections
a = 22.8120 (7) Å	θ = 2.1–30.4°
b = 10.5199 (4) Å	µ = 0.19 mm−1
c = 16.1346 (6) Å	T = 293 K
β = 103.926 (1)°	Block, white
V = 3758.2 (2) Å3	0.25 × 0.22 × 0.19 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	5682 independent reflections
Radiation source: fine-focus sealed tube	3487 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω and φ scans	θmax = 30.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→25
Tmin = 0.953, Tmax = 0.964	k = −11→14
24166 measured reflections	l = −22→23

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.069P)2 + 1.0112P] where P = (Fo2 + 2Fc2)/3
5682 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.36 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.

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
C5	0.02854 (9)	0.3172 (2)	0.15082 (14)	0.0761 (6)
H5	−0.0129	0.3160	0.1459	0.091*
C4	0.06108 (10)	0.2069 (2)	0.16354 (14)	0.0753 (6)
H4	0.0415	0.1303	0.1674	0.090*
C3	0.12244 (9)	0.20748 (18)	0.17070 (12)	0.0672 (5)
H3	0.1435	0.1310	0.1792	0.081*
C2	0.15354 (8)	0.31829 (16)	0.16568 (11)	0.0566 (4)
H2	0.1951	0.3180	0.1711	0.068*
C1	0.12076 (7)	0.42995 (16)	0.15223 (10)	0.0487 (3)
C6	0.05851 (7)	0.43214 (19)	0.14524 (11)	0.0593 (4)
C7	0.03865 (8)	0.5620 (2)	0.13190 (13)	0.0688 (5)
C8	0.08715 (7)	0.63472 (17)	0.13080 (11)	0.0581 (4)
C22	−0.02630 (10)	0.6044 (3)	0.1168 (2)	0.1116 (10)
H22A	−0.0304	0.6886	0.0930	0.167*
H22B	−0.0382	0.6047	0.1700	0.167*
H22C	−0.0517	0.5470	0.0777	0.167*
C9	0.08567 (9)	0.77369 (19)	0.11124 (13)	0.0692 (5)
C10	0.09789 (8)	0.82165 (16)	0.03063 (11)	0.0579 (4)
C11	0.07967 (9)	0.94417 (18)	0.00483 (13)	0.0683 (5)
H11	0.0613	0.9946	0.0387	0.082*
C12	0.08861 (10)	0.9915 (2)	−0.07082 (15)	0.0775 (6)
H12	0.0757	1.0731	−0.0883	0.093*
C13	0.11653 (10)	0.9185 (2)	−0.12028 (14)	0.0763 (6)
H13	0.1230	0.9514	−0.1709	0.092*
C14	0.13492 (9)	0.7980 (2)	−0.09585 (13)	0.0718 (5)
H14	0.1541	0.7491	−0.1296	0.086*
C15	0.12516 (8)	0.74826 (18)	−0.02105 (12)	0.0631 (4)
H15	0.1369	0.6653	−0.0053	0.076*
C16	0.20700 (7)	0.60409 (14)	0.30154 (10)	0.0485 (4)
C17	0.17865 (8)	0.69870 (17)	0.33647 (12)	0.0621 (4)
H17	0.1590	0.7650	0.3028	0.074*
C18	0.17995 (9)	0.6930 (2)	0.42209 (13)	0.0748 (6)
H18	0.1609	0.7560	0.4465	0.090*
C19	0.20885 (10)	0.5959 (2)	0.47163 (13)	0.0754 (6)
H19	0.2095	0.5933	0.5295	0.090*
C20	0.23697 (10)	0.5021 (2)	0.43652 (13)	0.0750 (6)
H20	0.2566	0.4362	0.4706	0.090*
C21	0.23613 (8)	0.50521 (17)	0.35097 (12)	0.0621 (4)
H21	0.2549	0.4416	0.3268	0.075*
N1	0.13917 (5)	0.55634 (13)	0.14070 (8)	0.0504 (3)
O1	0.24984 (5)	0.51956 (13)	0.17690 (8)	0.0667 (4)
O2	0.20878 (6)	0.73760 (13)	0.16764 (9)	0.0764 (4)
O3	0.06769 (10)	0.84532 (17)	0.15969 (12)	0.1136 (6)
S1	0.207048 (18)	0.60904 (4)	0.19323 (3)	0.05342 (14)

	U11	U22	U33	U12	U13	U23
C5	0.0493 (10)	0.0991 (16)	0.0790 (14)	−0.0230 (10)	0.0134 (9)	0.0018 (11)
C4	0.0763 (13)	0.0729 (13)	0.0756 (13)	−0.0247 (11)	0.0161 (10)	0.0001 (10)
C3	0.0762 (12)	0.0569 (10)	0.0683 (12)	−0.0079 (9)	0.0169 (10)	−0.0009 (9)
C2	0.0516 (9)	0.0594 (10)	0.0589 (10)	−0.0024 (7)	0.0134 (8)	−0.0002 (8)
C1	0.0422 (7)	0.0588 (9)	0.0442 (8)	−0.0075 (6)	0.0089 (6)	−0.0027 (7)
C6	0.0428 (8)	0.0773 (12)	0.0565 (10)	−0.0052 (8)	0.0093 (7)	0.0003 (9)
C7	0.0487 (9)	0.0880 (14)	0.0707 (12)	0.0101 (9)	0.0164 (9)	0.0053 (10)
C8	0.0535 (9)	0.0649 (10)	0.0564 (10)	0.0102 (8)	0.0142 (8)	0.0030 (8)
C22	0.0530 (12)	0.135 (2)	0.150 (3)	0.0246 (13)	0.0303 (14)	0.0199 (19)
C9	0.0755 (12)	0.0685 (12)	0.0652 (11)	0.0184 (10)	0.0200 (10)	−0.0017 (9)
C10	0.0531 (9)	0.0575 (10)	0.0594 (10)	0.0056 (7)	0.0063 (8)	−0.0012 (8)
C11	0.0672 (11)	0.0567 (10)	0.0796 (13)	0.0070 (9)	0.0145 (10)	−0.0024 (9)
C12	0.0796 (14)	0.0596 (12)	0.0886 (15)	−0.0007 (10)	0.0110 (12)	0.0145 (11)
C13	0.0770 (13)	0.0802 (14)	0.0694 (12)	−0.0102 (11)	0.0130 (10)	0.0121 (11)
C14	0.0691 (12)	0.0820 (14)	0.0641 (12)	0.0036 (10)	0.0158 (10)	−0.0001 (10)
C15	0.0643 (10)	0.0613 (10)	0.0604 (10)	0.0116 (8)	0.0089 (8)	0.0019 (8)
C16	0.0431 (7)	0.0449 (8)	0.0552 (9)	−0.0064 (6)	0.0075 (7)	−0.0017 (7)
C17	0.0603 (10)	0.0564 (10)	0.0655 (11)	0.0067 (8)	0.0072 (8)	−0.0034 (8)
C18	0.0669 (12)	0.0868 (14)	0.0714 (13)	0.0021 (10)	0.0183 (10)	−0.0201 (11)
C19	0.0761 (13)	0.0931 (16)	0.0565 (11)	−0.0167 (11)	0.0150 (10)	−0.0039 (11)
C20	0.0831 (14)	0.0692 (13)	0.0645 (12)	−0.0053 (10)	0.0020 (10)	0.0134 (10)
C21	0.0675 (11)	0.0514 (10)	0.0640 (11)	0.0036 (8)	0.0093 (9)	0.0005 (8)
N1	0.0422 (7)	0.0539 (8)	0.0537 (7)	−0.0025 (5)	0.0088 (6)	0.0010 (6)
O1	0.0425 (6)	0.0876 (9)	0.0726 (8)	−0.0042 (6)	0.0193 (6)	−0.0121 (7)
O2	0.0855 (9)	0.0646 (8)	0.0716 (8)	−0.0255 (7)	0.0043 (7)	0.0147 (6)
O3	0.1770 (18)	0.0842 (11)	0.0986 (12)	0.0421 (12)	0.0703 (13)	0.0065 (9)
S1	0.0469 (2)	0.0572 (3)	0.0552 (3)	−0.01117 (17)	0.01038 (17)	0.00133 (18)

C5—C4	1.366 (3)	C11—H11	0.9300
C5—C6	1.403 (3)	C12—C13	1.370 (3)
C5—H5	0.9300	C12—H12	0.9300
C4—C3	1.377 (3)	C13—C14	1.364 (3)
C4—H4	0.9300	C13—H13	0.9300
C3—C2	1.377 (2)	C14—C15	1.382 (3)
C3—H3	0.9300	C14—H14	0.9300
C2—C1	1.381 (2)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.379 (2)
C1—C6	1.397 (2)	C16—C21	1.380 (2)
C1—N1	1.420 (2)	C16—S1	1.7485 (17)
C6—C7	1.439 (3)	C17—C18	1.376 (3)
C7—C8	1.348 (3)	C17—H17	0.9300
C7—C22	1.510 (3)	C18—C19	1.365 (3)
C8—N1	1.422 (2)	C18—H18	0.9300
C8—C9	1.494 (3)	C19—C20	1.372 (3)
C22—H22A	0.9600	C19—H19	0.9300
C22—H22B	0.9600	C20—C21	1.376 (3)
C22—H22C	0.9600	C20—H20	0.9300
C9—O3	1.225 (2)	C21—H21	0.9300
C9—C10	1.483 (3)	N1—S1	1.6709 (13)
C10—C11	1.387 (3)	O1—S1	1.4257 (13)
C10—C15	1.389 (2)	O2—S1	1.4174 (13)
C11—C12	1.378 (3)
C4—C5—C6	119.11 (18)	C13—C12—C11	120.15 (19)
C4—C5—H5	120.4	C13—C12—H12	119.9
C6—C5—H5	120.4	C11—C12—H12	119.9
C5—C4—C3	120.89 (19)	C14—C13—C12	120.4 (2)
C5—C4—H4	119.6	C14—C13—H13	119.8
C3—C4—H4	119.6	C12—C13—H13	119.8
C4—C3—C2	121.80 (19)	C13—C14—C15	120.1 (2)
C4—C3—H3	119.1	C13—C14—H14	120.0
C2—C3—H3	119.1	C15—C14—H14	120.0
C3—C2—C1	117.52 (16)	C14—C15—C10	120.25 (18)
C3—C2—H2	121.2	C14—C15—H15	119.9
C1—C2—H2	121.2	C10—C15—H15	119.9
C2—C1—C6	121.86 (16)	C17—C16—C21	121.05 (17)
C2—C1—N1	130.61 (14)	C17—C16—S1	120.01 (13)
C6—C1—N1	107.51 (14)	C21—C16—S1	118.94 (13)
C1—C6—C5	118.82 (18)	C18—C17—C16	118.66 (17)
C1—C6—C7	107.75 (15)	C18—C17—H17	120.7
C5—C6—C7	133.42 (17)	C16—C17—H17	120.7
C8—C7—C6	108.09 (15)	C19—C18—C17	120.76 (19)
C8—C7—C22	127.3 (2)	C19—C18—H18	119.6
C6—C7—C22	124.5 (2)	C17—C18—H18	119.6
C7—C8—N1	109.56 (16)	C18—C19—C20	120.3 (2)
C7—C8—C9	125.49 (17)	C18—C19—H19	119.8
N1—C8—C9	124.53 (15)	C20—C19—H19	119.8
C7—C22—H22A	109.5	C19—C20—C21	120.12 (19)
C7—C22—H22B	109.5	C19—C20—H20	119.9
H22A—C22—H22B	109.5	C21—C20—H20	119.9
C7—C22—H22C	109.5	C20—C21—C16	119.10 (18)
H22A—C22—H22C	109.5	C20—C21—H21	120.5
H22B—C22—H22C	109.5	C16—C21—H21	120.5
O3—C9—C10	120.85 (19)	C1—N1—C8	107.01 (12)
O3—C9—C8	117.45 (19)	C1—N1—S1	120.76 (11)
C10—C9—C8	121.25 (16)	C8—N1—S1	120.73 (12)
C11—C10—C15	118.80 (18)	O2—S1—O1	120.52 (9)
C11—C10—C9	118.25 (17)	O2—S1—N1	104.85 (8)
C15—C10—C9	122.92 (16)	O1—S1—N1	106.22 (7)
C12—C11—C10	120.25 (19)	O2—S1—C16	109.05 (8)
C12—C11—H11	119.9	O1—S1—C16	109.29 (8)
C10—C11—H11	119.9	N1—S1—C16	105.88 (7)
C6—C5—C4—C3	−0.1 (3)	C13—C14—C15—C10	−1.5 (3)
C5—C4—C3—C2	0.2 (3)	C11—C10—C15—C14	1.3 (3)
C4—C3—C2—C1	−0.6 (3)	C9—C10—C15—C14	179.47 (18)
C3—C2—C1—C6	1.0 (3)	C21—C16—C17—C18	0.1 (3)
C3—C2—C1—N1	−176.99 (16)	S1—C16—C17—C18	−179.28 (14)
C2—C1—C6—C5	−1.0 (3)	C16—C17—C18—C19	0.2 (3)
N1—C1—C6—C5	177.45 (16)	C17—C18—C19—C20	−0.2 (3)
C2—C1—C6—C7	179.79 (16)	C18—C19—C20—C21	−0.1 (3)
N1—C1—C6—C7	−1.78 (19)	C19—C20—C21—C16	0.3 (3)
C4—C5—C6—C1	0.5 (3)	C17—C16—C21—C20	−0.4 (3)
C4—C5—C6—C7	179.5 (2)	S1—C16—C21—C20	179.02 (14)
C1—C6—C7—C8	0.1 (2)	C2—C1—N1—C8	−179.02 (17)
C5—C6—C7—C8	−179.0 (2)	C6—C1—N1—C8	2.74 (17)
C1—C6—C7—C22	176.8 (2)	C2—C1—N1—S1	−35.5 (2)
C5—C6—C7—C22	−2.2 (4)	C6—C1—N1—S1	146.23 (12)
C6—C7—C8—N1	1.6 (2)	C7—C8—N1—C1	−2.74 (19)
C22—C7—C8—N1	−175.0 (2)	C9—C8—N1—C1	−175.68 (16)
C6—C7—C8—C9	174.50 (17)	C7—C8—N1—S1	−146.25 (14)
C22—C7—C8—C9	−2.1 (3)	C9—C8—N1—S1	40.8 (2)
C7—C8—C9—O3	62.9 (3)	C1—N1—S1—O2	−178.64 (12)
N1—C8—C9—O3	−125.3 (2)	C8—N1—S1—O2	−40.07 (15)
C7—C8—C9—C10	−109.4 (2)	C1—N1—S1—O1	52.73 (14)
N1—C8—C9—C10	62.4 (3)	C8—N1—S1—O1	−168.70 (12)
O3—C9—C10—C11	−9.9 (3)	C1—N1—S1—C16	−63.40 (13)
C8—C9—C10—C11	162.15 (18)	C8—N1—S1—C16	75.17 (13)
O3—C9—C10—C15	171.9 (2)	C17—C16—S1—O2	33.31 (15)
C8—C9—C10—C15	−16.0 (3)	C21—C16—S1—O2	−146.06 (14)
C15—C10—C11—C12	0.0 (3)	C17—C16—S1—O1	166.94 (13)
C9—C10—C11—C12	−178.23 (18)	C21—C16—S1—O1	−12.44 (15)
C10—C11—C12—C13	−1.2 (3)	C17—C16—S1—N1	−79.03 (14)
C11—C12—C13—C14	1.0 (3)	C21—C16—S1—N1	101.60 (14)
C12—C13—C14—C15	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.45	3.025 (2)	120
C15—H15···N1	0.93	2.61	3.254 (2)	127
C21—H21···O1	0.93	2.53	2.904 (2)	104
C21—H21···O2i	0.93	2.29	3.127 (2)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.45	3.025 (2)	120
C15—H15⋯N1	0.93	2.61	3.254 (2)	127
C21—H21⋯O1	0.93	2.53	2.904 (2)	104
C21—H21⋯O2i	0.93	2.29	3.127 (2)	149

Symmetry code: (i) .