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

In the title compound, C(21)H(15)NO(3)S, the sulfonyl-bound phenyl ring forms a dihedral angle of 86.28 (5)° with the indole ring system. The mol-ecular structure is stabilized by intra-molecular C-H⋯O hydrogen bonds. The crystal packing is stabilized by weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C21H15NO3S

M = 361.40

Triclinic,

a = 7.567 (1) Å

b = 10.571 (2) Å

c = 12.083 (3) Å

α = 66.302 (2)°

β = 80.740 (1)°

γ = 78.403 (1)°

V = 863.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.960

15638 measured reflections

4276 independent reflections

3187 reflections with I > 2σ(I)

R int = 0.026

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.109

S = 1.01

4276 reflections

235 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.29 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042261/bt5379sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042261/bt5379Isup2.hkl

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

C21H15NO3S	Z = 2
Mr = 361.40	F(000) = 376
Triclinic, P1	Dx = 1.390 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.567 (1) Å	Cell parameters from 6196 reflections
b = 10.571 (2) Å	θ = 2.2–27.1°
c = 12.083 (3) Å	µ = 0.21 mm−1
α = 66.302 (2)°	T = 295 K
β = 80.740 (1)°	Block, colourless
γ = 78.403 (1)°	0.24 × 0.22 × 0.20 mm
V = 863.5 (3) Å3

Bruker Kappa APEXII diffractometer	4276 independent reflections
Radiation source: fine-focus sealed tube	3187 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.952, Tmax = 0.960	k = −14→13
15638 measured reflections	l = −16→16

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) = 0.109	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.1447P] where P = (Fo2 + 2Fc2)/3
4276 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.21 e Å−3
2 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.7233 (2)	0.05722 (16)	0.20701 (13)	0.0494 (4)
C2	0.6154 (3)	0.0869 (2)	0.29978 (15)	0.0648 (5)
H2	0.6523	0.1388	0.3360	0.078*
C3	0.4508 (3)	0.0376 (2)	0.33759 (18)	0.0791 (5)
H3	0.3759	0.0567	0.3997	0.095*
C4	0.3975 (3)	−0.0394 (2)	0.2838 (2)	0.0806 (6)
H4	0.2866	−0.0718	0.3097	0.097*
C5	0.5061 (3)	−0.0687 (2)	0.1928 (2)	0.0757 (5)
H5	0.4690	−0.1215	0.1575	0.091*
C6	0.6701 (2)	−0.02074 (19)	0.15289 (17)	0.0615 (4)
H6	0.7440	−0.0403	0.0906	0.074*
C14	0.80636 (19)	0.40437 (16)	0.04797 (13)	0.0448 (3)
C13	0.7914 (2)	0.44779 (18)	0.14366 (15)	0.0547 (4)
H13	0.8305	0.3873	0.2188	0.066*
C12	0.7164 (2)	0.5838 (2)	0.12251 (18)	0.0641 (5)
H12	0.7018	0.6157	0.1853	0.077*
C11	0.6617 (3)	0.6751 (2)	0.00966 (19)	0.0681 (5)
H11	0.6130	0.7671	−0.0019	0.082*
C10	0.6778 (2)	0.63262 (18)	−0.08489 (17)	0.0609 (4)
H10	0.6412	0.6948	−0.1603	0.073*
C9	0.75050 (19)	0.49375 (16)	−0.06607 (14)	0.0472 (3)
C8	0.7882 (2)	0.41551 (16)	−0.14359 (13)	0.0474 (3)
C7	0.86292 (19)	0.28383 (16)	−0.07641 (12)	0.0469 (3)
H7	0.8982	0.2113	−0.1040	0.056*
C15	0.7413 (2)	0.46868 (18)	−0.26928 (14)	0.0546 (4)
C16	0.8200 (2)	0.39033 (18)	−0.34881 (13)	0.0553 (4)
C21	0.9990 (3)	0.32957 (19)	−0.35204 (14)	0.0634 (5)
H21	1.0737	0.3291	−0.2978	0.076*
C20	1.0679 (3)	0.2692 (2)	−0.43577 (17)	0.0807 (6)
H20	1.1893	0.2301	−0.4391	0.097*
C19	0.9549 (4)	0.2676 (2)	−0.51451 (18)	0.0891 (6)
H19	1.0000	0.2259	−0.5700	0.107*
C18	0.7771 (4)	0.3274 (3)	−0.51087 (19)	0.0900 (6)
H18	0.7017	0.3266	−0.5642	0.108*
C17	0.7103 (3)	0.3879 (2)	−0.42929 (16)	0.0742 (5)
H17	0.5894	0.4283	−0.4275	0.089*
N1	0.87874 (17)	0.27365 (13)	0.04012 (10)	0.0461 (3)
O1	0.98538 (16)	0.15404 (13)	0.24616 (10)	0.0602 (3)
O2	1.04747 (14)	0.03484 (12)	0.10209 (10)	0.0543 (3)
O3	0.63449 (19)	0.57703 (15)	−0.30880 (11)	0.0789 (4)
S1	0.92933 (5)	0.12195 (4)	0.15505 (3)	0.04628 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0554 (8)	0.0428 (8)	0.0381 (7)	0.0021 (7)	−0.0076 (6)	−0.0064 (6)
C2	0.0723 (11)	0.0626 (11)	0.0470 (9)	−0.0010 (9)	0.0007 (8)	−0.0146 (8)
C3	0.0696 (12)	0.0795 (14)	0.0578 (11)	0.0037 (10)	0.0110 (9)	−0.0082 (9)
C4	0.0579 (10)	0.0687 (13)	0.0827 (14)	−0.0089 (9)	−0.0036 (10)	0.0032 (9)
C5	0.0669 (11)	0.0698 (13)	0.0848 (14)	−0.0156 (10)	−0.0104 (10)	−0.0201 (11)
C6	0.0619 (10)	0.0604 (11)	0.0593 (10)	−0.0069 (8)	−0.0060 (8)	−0.0209 (8)
C14	0.0447 (7)	0.0433 (8)	0.0444 (7)	−0.0093 (6)	−0.0023 (6)	−0.0140 (6)
C13	0.0606 (9)	0.0553 (10)	0.0513 (9)	−0.0105 (8)	−0.0034 (7)	−0.0234 (8)
C12	0.0666 (10)	0.0632 (12)	0.0739 (12)	−0.0113 (9)	−0.0011 (9)	−0.0391 (10)
C11	0.0712 (11)	0.0486 (10)	0.0844 (13)	−0.0044 (8)	−0.0049 (10)	−0.0280 (10)
C10	0.0611 (10)	0.0473 (9)	0.0632 (10)	−0.0049 (8)	−0.0074 (8)	−0.0107 (8)
C9	0.0440 (7)	0.0465 (8)	0.0456 (8)	−0.0096 (6)	−0.0016 (6)	−0.0115 (6)
C8	0.0483 (8)	0.0496 (9)	0.0386 (7)	−0.0083 (6)	−0.0041 (6)	−0.0105 (6)
C7	0.0535 (8)	0.0499 (9)	0.0359 (7)	−0.0072 (7)	−0.0052 (6)	−0.0149 (6)
C15	0.0546 (8)	0.0571 (10)	0.0403 (8)	−0.0080 (7)	−0.0082 (7)	−0.0053 (7)
C16	0.0677 (10)	0.0550 (10)	0.0337 (7)	−0.0120 (8)	−0.0094 (7)	−0.0041 (7)
C21	0.0728 (11)	0.0691 (12)	0.0399 (8)	−0.0044 (9)	−0.0087 (8)	−0.0138 (8)
C20	0.1019 (15)	0.0786 (14)	0.0471 (10)	0.0032 (12)	0.0000 (10)	−0.0194 (9)
C19	0.1479 (17)	0.0736 (14)	0.0441 (9)	−0.0172 (13)	−0.0036 (12)	−0.0223 (10)
C18	0.1306 (15)	0.0951 (17)	0.0512 (10)	−0.0334 (13)	−0.0220 (12)	−0.0222 (11)
C17	0.0873 (13)	0.0821 (14)	0.0465 (9)	−0.0182 (11)	−0.0203 (9)	−0.0097 (9)
N1	0.0566 (7)	0.0434 (7)	0.0357 (6)	−0.0037 (6)	−0.0071 (5)	−0.0132 (5)
O1	0.0728 (7)	0.0643 (7)	0.0457 (6)	−0.0020 (6)	−0.0197 (5)	−0.0220 (5)
O2	0.0551 (6)	0.0540 (7)	0.0498 (6)	0.0039 (5)	−0.0072 (5)	−0.0205 (5)
O3	0.0817 (9)	0.0791 (9)	0.0539 (7)	0.0174 (7)	−0.0184 (6)	−0.0119 (7)
S1	0.0526 (2)	0.0470 (2)	0.03579 (19)	0.00011 (16)	−0.00991 (15)	−0.01356 (15)

C1—C2	1.381 (2)	C10—H10	0.9300
C1—C6	1.386 (2)	C9—C8	1.444 (2)
C1—S1	1.7498 (17)	C8—C7	1.356 (2)
C2—C3	1.384 (3)	C8—C15	1.468 (2)
C2—H2	0.9300	C7—N1	1.3913 (18)
C3—C4	1.375 (3)	C7—H7	0.9300
C3—H3	0.9300	C15—O3	1.227 (2)
C4—C5	1.364 (3)	C15—C16	1.490 (2)
C4—H4	0.9300	C16—C21	1.379 (2)
C5—C6	1.376 (3)	C16—C17	1.387 (2)
C5—H5	0.9300	C21—C20	1.385 (3)
C6—H6	0.9300	C21—H21	0.9300
C14—C13	1.387 (2)	C20—C19	1.385 (3)
C14—C9	1.397 (2)	C20—H20	0.9300
C14—N1	1.4152 (19)	C19—C18	1.369 (3)
C13—C12	1.370 (2)	C19—H19	0.9300
C13—H13	0.9300	C18—C17	1.361 (3)
C12—C11	1.388 (3)	C18—H18	0.9300
C12—H12	0.9300	C17—H17	0.9300
C11—C10	1.366 (3)	N1—S1	1.6677 (12)
C11—H11	0.9300	O1—S1	1.4195 (11)
C10—C9	1.399 (2)	O2—S1	1.4195 (11)
C2—C1—C6	121.26 (17)	C7—C8—C9	107.38 (13)
C2—C1—S1	119.33 (14)	C7—C8—C15	127.21 (15)
C6—C1—S1	119.39 (12)	C9—C8—C15	125.29 (15)
C1—C2—C3	118.46 (19)	C8—C7—N1	109.68 (13)
C1—C2—H2	120.8	C8—C7—H7	125.2
C3—C2—H2	120.8	N1—C7—H7	125.2
C4—C3—C2	120.39 (18)	O3—C15—C8	119.99 (16)
C4—C3—H3	119.8	O3—C15—C16	119.61 (14)
C2—C3—H3	119.8	C8—C15—C16	120.39 (14)
C5—C4—C3	120.5 (2)	C21—C16—C17	118.93 (18)
C5—C4—H4	119.7	C21—C16—C15	123.05 (15)
C3—C4—H4	119.7	C17—C16—C15	117.84 (17)
C4—C5—C6	120.5 (2)	C16—C21—C20	120.24 (18)
C4—C5—H5	119.8	C16—C21—H21	119.9
C6—C5—H5	119.8	C20—C21—H21	119.9
C5—C6—C1	118.91 (18)	C21—C20—C19	119.5 (2)
C5—C6—H6	120.5	C21—C20—H20	120.2
C1—C6—H6	120.5	C19—C20—H20	120.2
C13—C14—C9	122.50 (15)	C18—C19—C20	120.2 (2)
C13—C14—N1	130.70 (14)	C18—C19—H19	119.9
C9—C14—N1	106.78 (13)	C20—C19—H19	119.9
C12—C13—C14	117.03 (16)	C17—C18—C19	120.1 (2)
C12—C13—H13	121.5	C17—C18—H18	120.0
C14—C13—H13	121.5	C19—C18—H18	120.0
C13—C12—C11	121.58 (17)	C18—C17—C16	121.0 (2)
C13—C12—H12	119.2	C18—C17—H17	119.5
C11—C12—H12	119.2	C16—C17—H17	119.5
C10—C11—C12	121.37 (17)	C7—N1—C14	108.35 (12)
C10—C11—H11	119.3	C7—N1—S1	123.27 (10)
C12—C11—H11	119.3	C14—N1—S1	126.91 (10)
C11—C10—C9	118.68 (17)	O2—S1—O1	120.91 (7)
C11—C10—H10	120.7	O2—S1—N1	105.43 (7)
C9—C10—H10	120.7	O1—S1—N1	106.66 (7)
C14—C9—C10	118.82 (15)	O2—S1—C1	108.92 (7)
C14—C9—C8	107.78 (14)	O1—S1—C1	109.22 (7)
C10—C9—C8	133.37 (15)	N1—S1—C1	104.41 (7)
C6—C1—C2—C3	−0.4 (3)	C8—C15—C16—C21	−42.0 (2)
S1—C1—C2—C3	178.44 (13)	O3—C15—C16—C17	−35.9 (2)
C1—C2—C3—C4	0.2 (3)	C8—C15—C16—C17	142.89 (16)
C2—C3—C4—C5	0.2 (3)	C17—C16—C21—C20	1.0 (3)
C3—C4—C5—C6	−0.5 (3)	C15—C16—C21—C20	−174.08 (16)
C4—C5—C6—C1	0.3 (3)	C16—C21—C20—C19	−1.4 (3)
C2—C1—C6—C5	0.2 (3)	C21—C20—C19—C18	1.1 (3)
S1—C1—C6—C5	−178.69 (14)	C20—C19—C18—C17	−0.4 (4)
C9—C14—C13—C12	0.7 (2)	C19—C18—C17—C16	0.0 (3)
N1—C14—C13—C12	178.95 (15)	C21—C16—C17—C18	−0.3 (3)
C14—C13—C12—C11	−1.5 (3)	C15—C16—C17—C18	175.06 (18)
C13—C12—C11—C10	1.0 (3)	C8—C7—N1—C14	1.51 (16)
C12—C11—C10—C9	0.3 (3)	C8—C7—N1—S1	168.55 (10)
C13—C14—C9—C10	0.5 (2)	C13—C14—N1—C7	−179.63 (15)
N1—C14—C9—C10	−178.11 (13)	C9—C14—N1—C7	−1.22 (16)
C13—C14—C9—C8	179.08 (14)	C13—C14—N1—S1	13.9 (2)
N1—C14—C9—C8	0.51 (16)	C9—C14—N1—S1	−167.65 (10)
C11—C10—C9—C14	−1.0 (2)	C7—N1—S1—O2	33.46 (13)
C11—C10—C9—C8	−179.16 (16)	C14—N1—S1—O2	−161.98 (12)
C14—C9—C8—C7	0.40 (16)	C7—N1—S1—O1	163.18 (12)
C10—C9—C8—C7	178.74 (17)	C14—N1—S1—O1	−32.27 (14)
C14—C9—C8—C15	176.58 (14)	C7—N1—S1—C1	−81.25 (13)
C10—C9—C8—C15	−5.1 (3)	C14—N1—S1—C1	83.30 (13)
C9—C8—C7—N1	−1.18 (17)	C2—C1—S1—O2	155.20 (12)
C15—C8—C7—N1	−177.26 (14)	C6—C1—S1—O2	−25.92 (15)
C7—C8—C15—O3	161.36 (17)	C2—C1—S1—O1	21.21 (15)
C9—C8—C15—O3	−14.1 (2)	C6—C1—S1—O1	−159.91 (13)
C7—C8—C15—C16	−17.5 (2)	C2—C1—S1—N1	−92.56 (13)
C9—C8—C15—C16	167.13 (14)	C6—C1—S1—N1	86.32 (14)
O3—C15—C16—C21	139.19 (18)

Cg1 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.59	2.934 (2)	103
C10—H10···O3	0.93	2.57	3.068 (3)	114
C13—H13···O1	0.93	2.42	2.999 (2)	120
C6—H6···O2i	0.93	2.58	3.493 (2)	167
C7—H7···O2i	0.93	2.54	3.429 (2)	160
C4—H4···Cg1ii	0.93	2.98	3.774 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.42	2.999 (2)	120
C6—H6⋯O2i	0.93	2.58	3.493 (2)	167
C7—H7⋯O2i	0.93	2.54	3.429 (2)	160
C4—H4⋯Cg1ii	0.93	2.98	3.774 (3)	144

Symmetry codes: (i) ; (ii) .