Crystal structure of (2-bromo-methyl-1-phenyl-sulfonyl-1H-indol-3-yl)(phen-yl)methanone.

In the title compound, C22H16BrNO3S, the phenyl rings make dihedral angles of 84.81 (16) and 61.67 (17)° with the indole ring system (r.m.s. deviation = 0.012 Å), while the phenyl rings are inclined to one another by 69.5 (2)°. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O hydrogen bonds. The sulfonyl S atom has a distorted tetra-hedral configuration. In the crystal, there are no significant inter-molecular inter-actions present.

Related literature

For the various biological properties of indole derivatives, see: Andreani et al. (2001 ▸); Bassindale (1984 ▸); Grinev et al. (1984 ▸); Porter et al. (1977 ▸); Rodriguez et al. (1985 ▸); Singh et al. (2000 ▸); Sundberg (1996 ▸). For the Thorpe–Ingold effect, see: Bassindale (1984 ▸). For the syntheses and crystal structures of similar compounds, see: Chakkaravarthi et al. (2008 ▸, 2009 ▸); Umadevi et al. (2013 ▸, 2014 ▸). For details concerning the Cambridge Structural Database, see: Groom & Allen (2014 ▸).

Experimental

Crystal data

C22H16BrNO3S

M = 454.33

Monoclinic,

a = 10.3629 (5) Å

b = 13.4156 (7) Å

c = 14.1777 (8) Å

β = 92.864 (2)°

V = 1968.59 (18) Å3

Z = 4

Mo Kα radiation

μ = 2.22 mm−1

T = 295 K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.596, T max = 0.665

34711 measured reflections

5017 independent reflections

3002 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.146

S = 1.06

5017 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.97 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 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989014028084/su5047sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014028084/su5047Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014028084/su5047Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014028084/su5047fig1.tif

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989014028084/su5047fig2.tif

A view approximately along the a axis of the crystal packing of the title compound.

CCDC reference: 1040945

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H16BrNO3S	F(000) = 920
Mr = 454.33	Dx = 1.533 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8313 reflections
a = 10.3629 (5) Å	θ = 2.3–23.1°
b = 13.4156 (7) Å	µ = 2.22 mm−1
c = 14.1777 (8) Å	T = 295 K
β = 92.864 (2)°	Block, colourless
V = 1968.59 (18) Å3	0.26 × 0.22 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	5017 independent reflections
Radiation source: fine-focus sealed tube	3002 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
ω and φ scan	θmax = 28.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.596, Tmax = 0.665	k = −18→18
34711 measured reflections	l = −19→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0515P)2 + 1.6826P] where P = (Fo2 + 2Fc2)/3
5017 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.97 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
C1	0.4019 (3)	0.3474 (2)	0.6542 (2)	0.0375 (7)
C2	0.4866 (3)	0.4214 (3)	0.6300 (3)	0.0476 (8)
H2	0.5662	0.4056	0.6064	0.057*
C3	0.4506 (4)	0.5192 (3)	0.6415 (3)	0.0609 (11)
H3	0.5067	0.5702	0.6262	0.073*
C4	0.3325 (4)	0.5421 (3)	0.6754 (3)	0.0571 (10)
H4	0.3093	0.6084	0.6830	0.069*
C5	0.2489 (4)	0.4687 (3)	0.6980 (3)	0.0583 (10)
H5	0.1688	0.4850	0.7205	0.070*
C6	0.2829 (3)	0.3700 (3)	0.6876 (3)	0.0493 (9)
H6	0.2262	0.3194	0.7030	0.059*
C7	0.2714 (3)	0.1711 (2)	0.5076 (2)	0.0374 (7)
C8	0.1644 (3)	0.1550 (3)	0.5608 (3)	0.0479 (8)
H8	0.1702	0.1566	0.6264	0.057*
C9	0.0499 (3)	0.1366 (3)	0.5115 (3)	0.0563 (10)
H9	−0.0238	0.1253	0.5447	0.068*
C10	0.0403 (3)	0.1341 (3)	0.4142 (3)	0.0587 (10)
H10	−0.0394	0.1210	0.3836	0.070*
C11	0.1456 (3)	0.1506 (3)	0.3619 (3)	0.0500 (9)
H11	0.1382	0.1500	0.2962	0.060*
C12	0.2641 (3)	0.1684 (2)	0.4096 (2)	0.0381 (7)
C13	0.3916 (3)	0.1867 (2)	0.3780 (2)	0.0382 (7)
C14	0.4730 (3)	0.2001 (2)	0.4550 (2)	0.0365 (7)
C15	0.6139 (3)	0.2080 (3)	0.4556 (3)	0.0461 (8)
H15A	0.6444	0.2520	0.5062	0.055*
H15B	0.6393	0.2362	0.3963	0.055*
C16	0.4326 (3)	0.1888 (3)	0.2792 (2)	0.0451 (8)
C17	0.3870 (3)	0.1104 (3)	0.2123 (2)	0.0437 (8)
C18	0.3509 (4)	0.0169 (3)	0.2420 (3)	0.0511 (9)
H18	0.3486	0.0030	0.3062	0.061*
C19	0.3180 (4)	−0.0558 (3)	0.1765 (3)	0.0663 (11)
H19	0.2937	−0.1189	0.1962	0.080*
C20	0.3213 (5)	−0.0347 (4)	0.0816 (3)	0.0753 (13)
H20	0.2992	−0.0839	0.0375	0.090*
C21	0.3566 (5)	0.0572 (4)	0.0519 (3)	0.0765 (14)
H21	0.3579	0.0709	−0.0124	0.092*
C22	0.3903 (4)	0.1298 (3)	0.1165 (3)	0.0595 (10)
H22	0.4155	0.1924	0.0960	0.071*
N1	0.4022 (2)	0.1883 (2)	0.53652 (18)	0.0379 (6)
O1	0.3769 (2)	0.16500 (18)	0.70726 (16)	0.0523 (6)
O2	0.5868 (2)	0.21867 (18)	0.65144 (17)	0.0500 (6)
O3	0.5064 (3)	0.2531 (2)	0.25507 (19)	0.0673 (8)
S1	0.44977 (8)	0.22304 (6)	0.64628 (6)	0.0400 (2)
Br1	0.69179 (4)	0.07623 (3)	0.47354 (4)	0.06721 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0397 (16)	0.0389 (17)	0.0338 (16)	−0.0043 (14)	0.0000 (13)	−0.0028 (13)
C2	0.0439 (18)	0.047 (2)	0.053 (2)	−0.0059 (15)	0.0085 (16)	−0.0017 (16)
C3	0.065 (3)	0.043 (2)	0.075 (3)	−0.0114 (19)	0.011 (2)	−0.0001 (19)
C4	0.072 (3)	0.041 (2)	0.059 (2)	0.0008 (19)	0.006 (2)	−0.0039 (18)
C5	0.055 (2)	0.055 (2)	0.066 (3)	0.0060 (19)	0.0141 (19)	−0.010 (2)
C6	0.048 (2)	0.047 (2)	0.054 (2)	−0.0087 (16)	0.0107 (16)	−0.0060 (17)
C7	0.0337 (15)	0.0378 (17)	0.0403 (18)	−0.0005 (13)	−0.0024 (13)	−0.0039 (14)
C8	0.0427 (18)	0.057 (2)	0.045 (2)	−0.0028 (16)	0.0077 (15)	−0.0062 (17)
C9	0.0365 (18)	0.067 (3)	0.067 (3)	−0.0023 (17)	0.0126 (17)	−0.008 (2)
C10	0.0331 (18)	0.077 (3)	0.065 (3)	−0.0014 (18)	−0.0076 (17)	−0.005 (2)
C11	0.0391 (18)	0.068 (2)	0.0424 (19)	0.0001 (17)	−0.0070 (15)	−0.0012 (17)
C12	0.0361 (16)	0.0366 (17)	0.0413 (18)	0.0045 (13)	−0.0005 (13)	−0.0007 (14)
C13	0.0371 (16)	0.0370 (17)	0.0404 (18)	−0.0005 (13)	0.0003 (13)	−0.0024 (14)
C14	0.0338 (15)	0.0350 (17)	0.0409 (18)	−0.0013 (13)	0.0038 (13)	−0.0030 (13)
C15	0.0409 (18)	0.046 (2)	0.051 (2)	−0.0076 (15)	0.0020 (15)	0.0005 (16)
C16	0.0419 (18)	0.048 (2)	0.045 (2)	−0.0019 (15)	0.0023 (15)	0.0027 (16)
C17	0.0375 (17)	0.054 (2)	0.0398 (19)	0.0025 (15)	0.0026 (14)	−0.0045 (16)
C18	0.057 (2)	0.049 (2)	0.047 (2)	0.0036 (17)	−0.0020 (16)	−0.0013 (17)
C19	0.073 (3)	0.053 (2)	0.072 (3)	0.003 (2)	−0.003 (2)	−0.011 (2)
C20	0.081 (3)	0.080 (3)	0.065 (3)	0.006 (3)	−0.004 (2)	−0.028 (3)
C21	0.082 (3)	0.108 (4)	0.039 (2)	−0.003 (3)	−0.001 (2)	−0.016 (2)
C22	0.064 (2)	0.070 (3)	0.045 (2)	−0.005 (2)	0.0068 (18)	0.002 (2)
N1	0.0352 (13)	0.0414 (15)	0.0370 (14)	−0.0019 (11)	0.0005 (11)	−0.0066 (12)
O1	0.0671 (16)	0.0479 (15)	0.0419 (14)	−0.0081 (12)	0.0011 (11)	0.0074 (11)
O2	0.0431 (13)	0.0536 (15)	0.0518 (14)	0.0059 (11)	−0.0122 (11)	−0.0047 (12)
O3	0.081 (2)	0.0693 (19)	0.0529 (16)	−0.0295 (15)	0.0130 (14)	−0.0012 (14)
S1	0.0418 (4)	0.0408 (5)	0.0368 (4)	−0.0016 (3)	−0.0048 (3)	−0.0001 (3)
Br1	0.0408 (2)	0.0659 (3)	0.0953 (4)	0.01197 (18)	0.0068 (2)	0.0010 (2)

C1—C6	1.378 (5)	C13—C14	1.357 (4)
C1—C2	1.379 (5)	C13—C16	1.483 (5)
C1—S1	1.746 (3)	C14—N1	1.409 (4)
C2—C3	1.377 (5)	C14—C15	1.463 (4)
C2—H2	0.9300	C15—Br1	1.955 (4)
C3—C4	1.371 (5)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.360 (5)	C16—O3	1.213 (4)
C4—H4	0.9300	C16—C17	1.479 (5)
C5—C6	1.380 (5)	C17—C18	1.381 (5)
C5—H5	0.9300	C17—C22	1.385 (5)
C6—H6	0.9300	C18—C19	1.378 (5)
C7—C8	1.388 (4)	C18—H18	0.9300
C7—C12	1.389 (4)	C19—C20	1.376 (7)
C7—N1	1.415 (4)	C19—H19	0.9300
C8—C9	1.370 (5)	C20—C21	1.360 (7)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.378 (5)	C21—C22	1.370 (6)
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.368 (5)	C22—H22	0.9300
C10—H10	0.9300	N1—S1	1.675 (3)
C11—C12	1.392 (4)	O1—S1	1.411 (2)
C11—H11	0.9300	O2—S1	1.419 (2)
C12—C13	1.438 (4)
C6—C1—C2	121.3 (3)	C13—C14—N1	108.5 (3)
C6—C1—S1	119.6 (3)	C13—C14—C15	126.4 (3)
C2—C1—S1	119.1 (3)	N1—C14—C15	124.3 (3)
C3—C2—C1	118.5 (3)	C14—C15—Br1	109.9 (2)
C3—C2—H2	120.8	C14—C15—H15A	109.7
C1—C2—H2	120.8	Br1—C15—H15A	109.7
C4—C3—C2	120.4 (4)	C14—C15—H15B	109.7
C4—C3—H3	119.8	Br1—C15—H15B	109.7
C2—C3—H3	119.8	H15A—C15—H15B	108.2
C5—C4—C3	120.8 (4)	O3—C16—C17	120.6 (3)
C5—C4—H4	119.6	O3—C16—C13	119.6 (3)
C3—C4—H4	119.6	C17—C16—C13	119.7 (3)
C4—C5—C6	120.0 (4)	C18—C17—C22	119.4 (3)
C4—C5—H5	120.0	C18—C17—C16	122.2 (3)
C6—C5—H5	120.0	C22—C17—C16	118.2 (3)
C1—C6—C5	119.0 (3)	C19—C18—C17	119.9 (4)
C1—C6—H6	120.5	C19—C18—H18	120.1
C5—C6—H6	120.5	C17—C18—H18	120.1
C8—C7—C12	122.3 (3)	C20—C19—C18	119.8 (4)
C8—C7—N1	130.4 (3)	C20—C19—H19	120.1
C12—C7—N1	107.3 (3)	C18—C19—H19	120.1
C9—C8—C7	116.5 (3)	C21—C20—C19	120.6 (4)
C9—C8—H8	121.7	C21—C20—H20	119.7
C7—C8—H8	121.7	C19—C20—H20	119.7
C8—C9—C10	122.2 (3)	C20—C21—C22	120.1 (4)
C8—C9—H9	118.9	C20—C21—H21	120.0
C10—C9—H9	118.9	C22—C21—H21	120.0
C11—C10—C9	121.3 (3)	C21—C22—C17	120.3 (4)
C11—C10—H10	119.4	C21—C22—H22	119.9
C9—C10—H10	119.4	C17—C22—H22	119.9
C10—C11—C12	118.2 (3)	C14—N1—C7	108.1 (2)
C10—C11—H11	120.9	C14—N1—S1	126.2 (2)
C12—C11—H11	120.9	C7—N1—S1	123.2 (2)
C7—C12—C11	119.6 (3)	O1—S1—O2	120.70 (15)
C7—C12—C13	107.6 (3)	O1—S1—N1	105.92 (14)
C11—C12—C13	132.8 (3)	O2—S1—N1	106.48 (14)
C14—C13—C12	108.4 (3)	O1—S1—C1	109.02 (15)
C14—C13—C16	124.1 (3)	O2—S1—C1	108.82 (15)
C12—C13—C16	127.5 (3)	N1—S1—C1	104.71 (14)
C6—C1—C2—C3	1.1 (5)	O3—C16—C17—C18	152.3 (4)
S1—C1—C2—C3	−176.4 (3)	C13—C16—C17—C18	−25.4 (5)
C1—C2—C3—C4	−0.7 (6)	O3—C16—C17—C22	−22.8 (5)
C2—C3—C4—C5	−0.1 (6)	C13—C16—C17—C22	159.5 (3)
C3—C4—C5—C6	0.5 (6)	C22—C17—C18—C19	−0.2 (5)
C2—C1—C6—C5	−0.8 (5)	C16—C17—C18—C19	−175.3 (4)
S1—C1—C6—C5	176.7 (3)	C17—C18—C19—C20	−0.1 (6)
C4—C5—C6—C1	0.0 (6)	C18—C19—C20—C21	0.0 (7)
C12—C7—C8—C9	−0.4 (5)	C19—C20—C21—C22	0.5 (8)
N1—C7—C8—C9	−177.5 (3)	C20—C21—C22—C17	−0.8 (7)
C7—C8—C9—C10	−0.1 (6)	C18—C17—C22—C21	0.7 (6)
C8—C9—C10—C11	−0.3 (7)	C16—C17—C22—C21	176.0 (4)
C9—C10—C11—C12	1.1 (6)	C13—C14—N1—C7	−2.4 (4)
C8—C7—C12—C11	1.2 (5)	C15—C14—N1—C7	−172.9 (3)
N1—C7—C12—C11	178.9 (3)	C13—C14—N1—S1	−164.8 (2)
C8—C7—C12—C13	−179.2 (3)	C15—C14—N1—S1	24.7 (4)
N1—C7—C12—C13	−1.5 (3)	C8—C7—N1—C14	179.9 (4)
C10—C11—C12—C7	−1.5 (5)	C12—C7—N1—C14	2.4 (3)
C10—C11—C12—C13	179.0 (4)	C8—C7—N1—S1	−17.1 (5)
C7—C12—C13—C14	0.0 (4)	C12—C7—N1—S1	165.4 (2)
C11—C12—C13—C14	179.5 (4)	C14—N1—S1—O1	−158.0 (3)
C7—C12—C13—C16	178.5 (3)	C7—N1—S1—O1	42.1 (3)
C11—C12—C13—C16	−1.9 (6)	C14—N1—S1—O2	−28.4 (3)
C12—C13—C14—N1	1.5 (4)	C7—N1—S1—O2	171.7 (2)
C16—C13—C14—N1	−177.1 (3)	C14—N1—S1—C1	86.8 (3)
C12—C13—C14—C15	171.7 (3)	C7—N1—S1—C1	−73.1 (3)
C16—C13—C14—C15	−6.9 (5)	C6—C1—S1—O1	−21.0 (3)
C13—C14—C15—Br1	−91.4 (4)	C2—C1—S1—O1	156.5 (3)
N1—C14—C15—Br1	77.3 (4)	C6—C1—S1—O2	−154.5 (3)
C14—C13—C16—O3	−43.9 (5)	C2—C1—S1—O2	23.0 (3)
C12—C13—C16—O3	137.8 (4)	C6—C1—S1—N1	92.0 (3)
C14—C13—C16—C17	133.8 (3)	C2—C1—S1—N1	−90.5 (3)
C12—C13—C16—C17	−44.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.38	2.953 (4)	120
C15—H15A···O2	0.97	2.22	2.808 (4)	118
C15—H15B···O3	0.97	2.38	3.062 (5)	127

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C8H8O1	0.93	2.38	2.953(4)	120
C15H15AO2	0.97	2.22	2.808(4)	118
C15H15BO3	0.97	2.38	3.062(5)	127