2-Bromo-1-(1-phenyl­sulfonyl-1H-indol-3-yl)propan-1-one

In the title compound, C₁₇H₁₄BrNO₃S, the phenyl ring makes a dihedral angle of 89.78 (16)° with the plane of the indole ring system. The terminal Br atom and the methyl group are disordered over two sets of sites, with site occupancies of 0.860 (2) and 0.140 (2). In the crystal, mol­ecules are linked into a chain along the b-axis direction by weak C—H...O hydrogen bonds. The chains are further linked by C—H...π inter­actions, forming layers parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.050
• wR factor = 0.149
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     --  O2      ..        5.4 su
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -3.334
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C16    --  C17     ..       12.5 su
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C16    --  C17A    ..        6.5 su
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          9 Note
PLAT793_ALERT_4_G The Model has Chirality at C16          (Verify)          R
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          5 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         76

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: All the six authors have contribution in this paper. 1st and 3rd authors are students involved in the synthesis, preparation of the sample and basic crystallography. 2nd author is the supervisor of 1st author. 4th author is the supervisor of 3rd author.6th author is co-supervisors of 1st author. 5th author is involved in final crystallography and writeup and also involved in the biological study.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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S1. Comment

Indole derivatives exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). These derivatives also exhibit antimicrobial, antibiotic, analgesic, anticancer and anti-HIV (Pomarnacka & Kozlarska-Kedra, 2003; Srivastava & Pandeya, 2011) activities.

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Umadevi et al., 2013; Kanchanadevi et al., 2014). The phenyl ring makes a dihedral angle of 89.78 (16)° with the indole ring system. The terminal bromine atom and the methyl group are disordered over two positions with site occupancies of 0.860 (2) and 0.140 (2). The sum of bond angles around the atom N1 [356.7 (3) °] indicates sp² hybridized state of atom N1 in the molecule. The crystal packing is controlled by weak C—H···O and C—H···π interactions (Table 1).

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001); Singh et al. (2000); Pomarnacka & Kozlarska-Kedra (2003); Srivastava & Pandeya (2011). For related structures, see: Umadevi et al. (2013); Kanchanadevi et al. (2014).

S2. Experimental

A solution of 1-[1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one (1 g, 3.194 mmol) and PTT (phenyltrimethylammonium tribromide) (1.32 g, 3.514 mmol) in dry THF (20 ml) was stirred at room temperature for 3 h. After completion of the reaction (monitored by TLC), it was poured into crushed ice (100 g). The solid obtained was filtered and washed with MeOH (5 ml) to afford 2-bromo-1-[1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one (1.14 g, yield 91%; melting point 130–132 °C).

S3. Refinement

The terminal bromine atom and the methyl group are disordered over two positions. The site occupancy factors of disordered atoms were refined to 0.860 (2) and 0.140 (2). In the refinement, EADP was used for atoms C17 and C17A. The bond distances of C16—C17 and C16—C17A were restrained to be 1.5200 (1) and 1.5200 (5) Å, respectively, and the distances of C16—Br1 and C16—Br1A were restrained to be 1.9100 (1) and 1.9100 (5) Å, respectively. Also the distance of C17A···Br1A was restrained to be 2.85 (1) Å. H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for aromatic C—H, C—H = 0.98 Å and U_iso(H) = 1.2U_eq(C) for C—H, C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) for CH₃.

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing diagram of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.

2-Bromo-1-(1-phenylsulfonyl-1H-indol-3-yl)propan-1-one

Crystal data

C17H14BrNO3S	F(000) = 792
Mr = 392.26	Dx = 1.560 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4350 reflections
a = 8.7539 (3) Å	θ = 2.2–28.4°
b = 10.9968 (4) Å	µ = 2.60 mm^−1
c = 17.5801 (7) Å	T = 295 K
β = 99.231 (2)°	Block, yellow
V = 1670.43 (11) Å^3	0.35 × 0.25 × 0.25 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	4141 independent reflections
Radiation source: fine-focus sealed tube	2334 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 0 pixels mm^-1	θmax = 28.5°, θmin = 2.2°
ω and φ scans	h = −11→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→14
Tmin = 0.416, Tmax = 0.522	l = −21→23
15009 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0673P)^2 + 0.7073P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4141 reflections	Δρmax = 0.41 e Å^−3
222 parameters	Δρmin = −0.51 e Å^−3
5 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (9)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.7170 (3)	0.2542 (3)	0.30787 (16)	0.0382 (7)
C2	0.6804 (4)	0.1348 (3)	0.28691 (18)	0.0480 (8)
H2	0.7480	0.0850	0.2655	0.058*
C3	0.5365 (4)	0.0944 (3)	0.2998 (2)	0.0558 (9)
H3	0.5071	0.0148	0.2870	0.067*
C4	0.4359 (4)	0.1688 (3)	0.3310 (2)	0.0627 (10)
H4	0.3398	0.1387	0.3380	0.075*
C5	0.4753 (4)	0.2878 (3)	0.3522 (2)	0.0552 (9)
H5	0.4072	0.3373	0.3735	0.066*
C6	0.6184 (3)	0.3308 (3)	0.34090 (16)	0.0392 (7)
C7	0.6963 (3)	0.4468 (2)	0.35599 (16)	0.0391 (7)
C8	0.8349 (3)	0.4370 (2)	0.33195 (16)	0.0375 (7)
H8	0.9074	0.4992	0.3341	0.045*
C9	0.8963 (3)	0.3192 (3)	0.15480 (17)	0.0427 (7)
C10	0.9085 (4)	0.4343 (3)	0.12403 (19)	0.0587 (9)
H10	0.9658	0.4947	0.1527	0.070*
C11	0.8349 (5)	0.4573 (4)	0.0508 (2)	0.0803 (12)
H11	0.8417	0.5339	0.0292	0.096*
C12	0.7501 (5)	0.3665 (4)	0.0088 (2)	0.0820 (13)
H12	0.6992	0.3830	−0.0407	0.098*
C13	0.7405 (5)	0.2530 (4)	0.0393 (2)	0.0804 (13)
H13	0.6845	0.1926	0.0101	0.096*
C14	0.8121 (4)	0.2279 (3)	0.1120 (2)	0.0614 (9)
H14	0.8050	0.1508	0.1329	0.074*
C15	0.6362 (4)	0.5538 (3)	0.39046 (19)	0.0511 (8)
C16	0.7409 (4)	0.6635 (2)	0.40341 (9)	0.0651 (10)
H16A	0.8186	0.6547	0.3694	0.078*	0.860 (2)
H16B	0.7916	0.6656	0.3576	0.078*	0.140 (2)
Br1	0.84813 (7)	0.65595 (6)	0.50680 (4)	0.0973 (3)	0.860 (2)
C17	0.6681 (10)	0.7883 (4)	0.3880 (5)	0.0539 (15)	0.860 (2)
H17A	0.7036	0.8411	0.4307	0.081*	0.860 (2)
H17B	0.5575	0.7812	0.3817	0.081*	0.860 (2)
H17C	0.6973	0.8215	0.3419	0.081*	0.860 (2)
Br1A	0.6298 (11)	0.8071 (6)	0.3977 (7)	0.132 (4)	0.140 (2)
C17A	0.875 (2)	0.6591 (18)	0.4701 (12)	0.0539 (15)	0.140 (2)
H17D	0.9557	0.7124	0.4596	0.081*	0.140 (2)
H17E	0.9138	0.5775	0.4763	0.081*	0.140 (2)
H17F	0.8396	0.6846	0.5166	0.081*	0.140 (2)
N1	0.8539 (3)	0.3213 (2)	0.30363 (13)	0.0384 (6)
O1	1.0168 (3)	0.16368 (19)	0.25653 (14)	0.0591 (6)
O2	1.1079 (2)	0.3760 (2)	0.27067 (13)	0.0526 (6)
O3	0.5058 (3)	0.5548 (2)	0.40600 (18)	0.0778 (8)
S1	0.98775 (9)	0.29060 (7)	0.24862 (4)	0.0422 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0438 (16)	0.0389 (15)	0.0298 (16)	0.0014 (13)	−0.0003 (12)	0.0057 (12)
C2	0.059 (2)	0.0392 (17)	0.0421 (19)	−0.0028 (14)	−0.0019 (15)	0.0011 (13)
C3	0.060 (2)	0.0464 (18)	0.056 (2)	−0.0136 (17)	−0.0088 (16)	0.0034 (16)
C4	0.0454 (19)	0.065 (2)	0.074 (3)	−0.0139 (18)	−0.0001 (17)	0.0101 (19)
C5	0.0441 (18)	0.058 (2)	0.063 (2)	0.0016 (16)	0.0069 (15)	0.0098 (17)
C6	0.0413 (16)	0.0405 (15)	0.0340 (16)	0.0009 (13)	0.0004 (12)	0.0080 (12)
C7	0.0454 (16)	0.0353 (15)	0.0355 (16)	0.0031 (13)	0.0034 (12)	0.0027 (12)
C8	0.0464 (17)	0.0298 (14)	0.0357 (16)	−0.0021 (12)	0.0047 (12)	−0.0002 (11)
C9	0.0470 (17)	0.0435 (17)	0.0393 (17)	0.0018 (13)	0.0115 (13)	−0.0037 (13)
C10	0.083 (2)	0.0438 (19)	0.047 (2)	−0.0007 (17)	0.0053 (18)	−0.0021 (15)
C11	0.118 (4)	0.063 (2)	0.056 (3)	0.003 (2)	0.004 (2)	0.010 (2)
C12	0.097 (3)	0.107 (4)	0.037 (2)	−0.008 (3)	−0.004 (2)	−0.001 (2)
C13	0.099 (3)	0.098 (3)	0.042 (2)	−0.033 (3)	0.008 (2)	−0.012 (2)
C14	0.078 (2)	0.061 (2)	0.047 (2)	−0.0192 (19)	0.0146 (18)	−0.0042 (17)
C15	0.057 (2)	0.051 (2)	0.047 (2)	0.0062 (16)	0.0141 (16)	0.0018 (14)
C16	0.080 (3)	0.051 (2)	0.070 (3)	−0.0090 (18)	0.029 (2)	−0.0180 (17)
Br1	0.0956 (5)	0.0997 (5)	0.0870 (5)	−0.0029 (3)	−0.0142 (3)	−0.0100 (3)
C17	0.067 (4)	0.023 (2)	0.071 (4)	0.016 (2)	0.008 (3)	0.009 (2)
Br1A	0.118 (6)	0.078 (3)	0.192 (7)	0.027 (3)	0.004 (4)	−0.038 (4)
C17A	0.067 (4)	0.023 (2)	0.071 (4)	0.016 (2)	0.008 (3)	0.009 (2)
N1	0.0432 (14)	0.0363 (13)	0.0356 (14)	−0.0015 (10)	0.0062 (10)	−0.0010 (10)
O1	0.0659 (15)	0.0400 (12)	0.0727 (17)	0.0185 (10)	0.0151 (12)	0.0072 (10)
O2	0.0369 (11)	0.0555 (13)	0.0640 (15)	−0.0048 (10)	0.0040 (10)	−0.0037 (11)
O3	0.0651 (17)	0.0646 (16)	0.111 (2)	0.0071 (13)	0.0367 (16)	−0.0143 (15)
S1	0.0431 (4)	0.0378 (4)	0.0458 (5)	0.0067 (3)	0.0078 (3)	0.0012 (3)

Geometric parameters (Å, º)

C1—C2	1.387 (4)	C12—C13	1.366 (6)
C1—C6	1.398 (4)	C12—H12	0.9300
C1—N1	1.420 (4)	C13—C14	1.359 (5)
C2—C3	1.388 (5)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.379 (5)	C15—O3	1.216 (4)
C3—H3	0.9300	C15—C16	1.511 (4)
C4—C5	1.389 (5)	C16—C17	1.5190 (10)
C4—H4	0.9300	C16—C17A	1.520 (5)
C5—C6	1.382 (4)	C16—Br1A	1.849 (4)
C5—H5	0.9300	C16—Br1	1.9092 (10)
C6—C7	1.450 (4)	C16—H16A	0.9800
C7—C8	1.352 (4)	C16—H16B	0.9800
C7—C15	1.460 (4)	C17—H17A	0.9600
C8—N1	1.386 (3)	C17—H17B	0.9600
C8—H8	0.9300	C17—H17C	0.9600
C9—C10	1.388 (4)	C17A—H17D	0.9600
C9—C14	1.392 (5)	C17A—H17E	0.9600
C9—S1	1.743 (3)	C17A—H17F	0.9600
C10—C11	1.368 (5)	N1—S1	1.669 (2)
C10—H10	0.9300	O1—S1	1.422 (2)
C11—C12	1.384 (6)	O2—S1	1.417 (2)
C11—H11	0.9300
C2—C1—C6	123.3 (3)	C13—C14—C9	119.1 (3)
C2—C1—N1	129.7 (3)	C13—C14—H14	120.5
C6—C1—N1	107.0 (2)	C9—C14—H14	120.5
C1—C2—C3	115.9 (3)	O3—C15—C7	121.0 (3)
C1—C2—H2	122.0	O3—C15—C16	121.8 (3)
C3—C2—H2	122.0	C7—C15—C16	117.1 (3)
C4—C3—C2	121.9 (3)	C15—C16—C17	117.9 (4)
C4—C3—H3	119.0	C15—C16—C17A	117.7 (10)
C2—C3—H3	119.0	C15—C16—Br1A	111.9 (4)
C3—C4—C5	121.3 (3)	C17A—C16—Br1A	113.8 (6)
C3—C4—H4	119.4	C15—C16—Br1	107.61 (19)
C5—C4—H4	119.4	C17—C16—Br1	109.7 (4)
C6—C5—C4	118.4 (3)	C15—C16—H16A	107.0
C6—C5—H5	120.8	C17—C16—H16A	107.0
C4—C5—H5	120.8	Br1—C16—H16A	107.0
C5—C6—C1	119.2 (3)	C15—C16—H16B	103.8
C5—C6—C7	133.2 (3)	C17A—C16—H16B	103.8
C1—C6—C7	107.6 (2)	Br1A—C16—H16B	103.8
C8—C7—C6	107.0 (2)	C16—C17—H17A	109.5
C8—C7—C15	126.5 (3)	C16—C17—H17B	109.5
C6—C7—C15	126.5 (3)	H17A—C17—H17B	109.5
C7—C8—N1	110.6 (2)	C16—C17—H17C	109.5
C7—C8—H8	124.7	H17A—C17—H17C	109.5
N1—C8—H8	124.7	H17B—C17—H17C	109.5
C10—C9—C14	121.0 (3)	C16—C17A—H17D	109.5
C10—C9—S1	118.7 (2)	C16—C17A—H17E	109.5
C14—C9—S1	120.3 (2)	H17D—C17A—H17E	109.5
C11—C10—C9	118.8 (3)	C16—C17A—H17F	109.5
C11—C10—H10	120.6	H17D—C17A—H17F	109.5
C9—C10—H10	120.6	H17E—C17A—H17F	109.5
C10—C11—C12	120.0 (4)	C8—N1—C1	107.9 (2)
C10—C11—H11	120.0	C8—N1—S1	122.02 (19)
C12—C11—H11	120.0	C1—N1—S1	127.03 (19)
C13—C12—C11	120.7 (4)	O2—S1—O1	120.71 (14)
C13—C12—H12	119.6	O2—S1—N1	105.46 (12)
C11—C12—H12	119.6	O1—S1—N1	105.86 (13)
C14—C13—C12	120.4 (4)	O2—S1—C9	110.36 (14)
C14—C13—H13	119.8	O1—S1—C9	108.50 (14)
C12—C13—H13	119.8	N1—S1—C9	104.67 (13)
C6—C1—C2—C3	0.7 (4)	C6—C7—C15—C16	177.8 (2)
N1—C1—C2—C3	178.7 (3)	O3—C15—C16—C17	−37.3 (5)
C1—C2—C3—C4	0.5 (5)	C7—C15—C16—C17	140.8 (4)
C2—C3—C4—C5	−1.1 (5)	O3—C15—C16—C17A	106.8 (12)
C3—C4—C5—C6	0.4 (5)	C7—C15—C16—C17A	−75.1 (12)
C4—C5—C6—C1	0.8 (4)	O3—C15—C16—Br1A	−27.8 (5)
C4—C5—C6—C7	−179.8 (3)	C7—C15—C16—Br1A	150.3 (4)
C2—C1—C6—C5	−1.4 (4)	O3—C15—C16—Br1	87.4 (3)
N1—C1—C6—C5	−179.7 (2)	C7—C15—C16—Br1	−94.5 (3)
C2—C1—C6—C7	179.1 (3)	C7—C8—N1—C1	1.7 (3)
N1—C1—C6—C7	0.7 (3)	C7—C8—N1—S1	163.2 (2)
C5—C6—C7—C8	−179.2 (3)	C2—C1—N1—C8	−179.7 (3)
C1—C6—C7—C8	0.3 (3)	C6—C1—N1—C8	−1.5 (3)
C5—C6—C7—C15	0.7 (5)	C2—C1—N1—S1	20.1 (4)
C1—C6—C7—C15	−179.8 (3)	C6—C1—N1—S1	−161.7 (2)
C6—C7—C8—N1	−1.3 (3)	C8—N1—S1—O2	28.1 (2)
C15—C7—C8—N1	178.9 (3)	C1—N1—S1—O2	−174.2 (2)
C14—C9—C10—C11	0.7 (5)	C8—N1—S1—O1	157.1 (2)
S1—C9—C10—C11	−179.1 (3)	C1—N1—S1—O1	−45.2 (3)
C9—C10—C11—C12	0.0 (6)	C8—N1—S1—C9	−88.4 (2)
C10—C11—C12—C13	−0.8 (7)	C1—N1—S1—C9	69.3 (2)
C11—C12—C13—C14	1.1 (7)	C10—C9—S1—O2	−21.3 (3)
C12—C13—C14—C9	−0.4 (6)	C14—C9—S1—O2	158.9 (3)
C10—C9—C14—C13	−0.4 (5)	C10—C9—S1—O1	−155.7 (3)
S1—C9—C14—C13	179.3 (3)	C14—C9—S1—O1	24.6 (3)
C8—C7—C15—O3	175.7 (3)	C10—C9—S1—N1	91.7 (3)
C6—C7—C15—O3	−4.1 (5)	C14—C9—S1—N1	−88.0 (3)
C8—C7—C15—C16	−2.4 (4)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.93	2.57	3.312 (4)	137
C10—H10···O1^i	0.93	2.44	3.280 (4)	150
C12—H12···Cg2^ii	0.93	2.72	3.528 (2)	146

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2.