3-Benzyl-2-methyl-1-phenyl­sulfonyl-1H-indole

In the title compound, C₂₂H₁₉NO₂S, the two phenyl rings adopt a trans conformation with respect to the indole moiety. The indole system deviates slightly from planarity. The aromatic ring of the phenyl­sulfonyl group is almost perpendicular to the indole ring, while the benzyl ring is oriented at an angle of 77.01 (1)°. A zigzag C—H...O intermolecular hydrogen bond along the b axis and C—H...π interactions stabilize the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.143
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H17    ..  CG2     ..       3.27 Ang.

Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.94
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C26
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  CG1     ..       3.09 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  CG2     ..       3.05 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C5     ..  CG1     ..       4.02 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003), ORTEP-3 (Farrugia, 1997) and ZORTEP (Zsolnai, 1998); software used to prepare material for publication: PLATON.

3-Benzyl-2-methyl-1-phenylsulfonyl-1H-indole

Crystal data

C22H19NO2S	F(000) = 1520
Mr = 361.44	Dx = 1.311 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 26996 reflections
a = 17.160 (9) Å	θ = 2.2–27.3°
b = 11.680 (6) Å	µ = 0.19 mm^−1
c = 18.274 (10) Å	T = 293 K
V = 3663 (3) Å^3	Block, colourless
Z = 8	0.25 × 0.22 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3235 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 27.3°, θmin = 2.2°
ω scans	h = −21→21
26996 measured reflections	k = −15→15
3882 independent reflections	l = −22→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0872P)^2 + 1.131P] where P = (Fo^2 + 2Fc^2)/3
3882 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
N1	−0.00791 (8)	0.22112 (11)	0.37854 (8)	0.0397 (3)
C2	−0.03940 (10)	0.11464 (14)	0.35339 (9)	0.0409 (4)
C3	−0.07236 (9)	0.06007 (14)	0.41067 (10)	0.0410 (4)
C4	−0.06201 (9)	0.12922 (15)	0.47543 (10)	0.0414 (4)
C5	−0.08523 (11)	0.11487 (19)	0.54840 (10)	0.0553 (5)
H5	−0.1124	0.0497	0.5627	0.066*
C6	−0.06719 (12)	0.1983 (2)	0.59841 (12)	0.0664 (6)
H6	−0.0817	0.1891	0.6471	0.080*
C7	−0.02750 (13)	0.2966 (2)	0.57716 (11)	0.0636 (6)
H7	−0.0163	0.3522	0.6120	0.076*
C8	−0.00422 (11)	0.31393 (17)	0.50577 (11)	0.0515 (4)
H8	0.0219	0.3802	0.4919	0.062*
C9	−0.02135 (9)	0.22825 (13)	0.45527 (9)	0.0388 (4)
S10	0.06544 (3)	0.28871 (4)	0.33743 (2)	0.04496 (17)
O11	0.07039 (8)	0.39829 (11)	0.37166 (9)	0.0583 (4)
O12	0.05223 (10)	0.28127 (13)	0.26045 (8)	0.0653 (4)
C13	0.14927 (10)	0.20972 (14)	0.35915 (10)	0.0452 (4)
C14	0.18895 (11)	0.23174 (17)	0.42383 (11)	0.0529 (5)
H14	0.1717	0.2887	0.4554	0.063*
C15	0.25439 (12)	0.1681 (2)	0.44076 (13)	0.0670 (6)
H15	0.2816	0.1825	0.4838	0.080*
C16	0.27912 (14)	0.0841 (2)	0.39433 (18)	0.0798 (7)
H16	0.3229	0.0410	0.4063	0.096*
C17	0.24033 (17)	0.0626 (2)	0.33033 (18)	0.0886 (8)
H17	0.2581	0.0056	0.2990	0.106*
C18	0.17480 (14)	0.1254 (2)	0.31213 (14)	0.0707 (6)
H18	0.1483	0.1109	0.2687	0.085*
C19	−0.11374 (11)	−0.05304 (15)	0.40720 (12)	0.0521 (5)
H19A	−0.0876	−0.1007	0.3713	0.063*
H19B	−0.1085	−0.0904	0.4543	0.063*
C20	−0.19930 (10)	−0.04776 (14)	0.38800 (10)	0.0446 (4)
C21	−0.24606 (12)	0.04350 (17)	0.40759 (12)	0.0589 (5)
H21	−0.2239	0.1065	0.4307	0.071*
C22	−0.32522 (13)	0.0428 (2)	0.39352 (15)	0.0725 (6)
H22	−0.3558	0.1049	0.4072	0.087*
C23	−0.35835 (14)	−0.0489 (2)	0.35957 (16)	0.0819 (8)
H23	−0.4117	−0.0499	0.3506	0.098*
C24	−0.31301 (17)	−0.1394 (3)	0.33872 (17)	0.0866 (8)
H24	−0.3358	−0.2017	0.3153	0.104*
C25	−0.23324 (14)	−0.13931 (19)	0.35206 (13)	0.0659 (6)
H25	−0.2028	−0.2007	0.3369	0.079*
C26	−0.04056 (15)	0.07885 (19)	0.27470 (12)	0.0659 (6)
H26A	−0.0121	0.1335	0.2459	0.099*
H26B	−0.0935	0.0753	0.2578	0.099*
H26C	−0.0168	0.0048	0.2699	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0381 (7)	0.0363 (7)	0.0447 (8)	−0.0038 (5)	−0.0017 (6)	−0.0003 (5)
C2	0.0376 (8)	0.0363 (8)	0.0488 (9)	−0.0017 (6)	−0.0040 (7)	−0.0043 (7)
C3	0.0327 (8)	0.0358 (8)	0.0546 (10)	0.0022 (6)	−0.0040 (7)	0.0018 (7)
C4	0.0313 (8)	0.0453 (9)	0.0475 (9)	0.0039 (6)	−0.0033 (6)	0.0045 (7)
C5	0.0438 (10)	0.0713 (13)	0.0509 (11)	0.0011 (9)	0.0023 (8)	0.0125 (9)
C6	0.0540 (12)	0.1034 (19)	0.0418 (11)	0.0104 (11)	0.0027 (8)	−0.0020 (11)
C7	0.0534 (12)	0.0838 (15)	0.0537 (12)	0.0068 (10)	−0.0058 (9)	−0.0227 (10)
C8	0.0441 (9)	0.0532 (10)	0.0571 (11)	0.0003 (8)	−0.0050 (8)	−0.0121 (8)
C9	0.0317 (7)	0.0413 (8)	0.0434 (9)	0.0034 (6)	−0.0040 (6)	−0.0013 (6)
S10	0.0469 (3)	0.0390 (3)	0.0489 (3)	−0.00585 (16)	−0.00116 (17)	0.00997 (17)
O11	0.0563 (8)	0.0356 (7)	0.0831 (10)	−0.0068 (5)	−0.0039 (7)	0.0061 (6)
O12	0.0756 (10)	0.0723 (10)	0.0479 (8)	−0.0114 (7)	−0.0043 (7)	0.0209 (7)
C13	0.0413 (9)	0.0446 (9)	0.0497 (9)	−0.0047 (7)	0.0087 (7)	0.0046 (7)
C14	0.0442 (10)	0.0585 (11)	0.0559 (11)	0.0012 (8)	0.0031 (8)	0.0015 (8)
C15	0.0462 (11)	0.0772 (14)	0.0776 (14)	0.0031 (10)	−0.0016 (10)	0.0105 (12)
C16	0.0478 (12)	0.0689 (15)	0.123 (2)	0.0111 (11)	0.0093 (13)	0.0061 (14)
C17	0.0649 (15)	0.0796 (17)	0.121 (2)	0.0127 (13)	0.0174 (15)	−0.0320 (16)
C18	0.0606 (13)	0.0784 (15)	0.0731 (14)	0.0022 (11)	0.0084 (11)	−0.0214 (12)
C19	0.0419 (9)	0.0377 (9)	0.0768 (13)	−0.0029 (7)	−0.0030 (8)	0.0044 (8)
C20	0.0411 (9)	0.0406 (9)	0.0519 (10)	−0.0072 (7)	0.0016 (7)	0.0067 (7)
C21	0.0454 (10)	0.0557 (11)	0.0756 (13)	0.0007 (9)	−0.0038 (9)	−0.0034 (9)
C22	0.0441 (11)	0.0769 (15)	0.0964 (17)	0.0046 (10)	0.0032 (11)	0.0158 (13)
C23	0.0465 (12)	0.0886 (18)	0.111 (2)	−0.0200 (12)	−0.0179 (12)	0.0331 (16)
C24	0.0752 (17)	0.0729 (16)	0.112 (2)	−0.0336 (14)	−0.0261 (15)	0.0033 (14)
C25	0.0662 (14)	0.0485 (11)	0.0829 (15)	−0.0152 (10)	−0.0080 (11)	−0.0027 (10)
C26	0.0754 (14)	0.0648 (13)	0.0576 (12)	−0.0162 (11)	0.0046 (10)	−0.0184 (10)

Geometric parameters (Å, º)

N1—C9	1.424 (2)	C15—C16	1.365 (4)
N1—C2	1.432 (2)	C15—H15	0.9300
N1—S10	1.6650 (15)	C16—C17	1.369 (4)
C2—C3	1.350 (2)	C16—H16	0.9300
C2—C26	1.498 (3)	C17—C18	1.383 (4)
C3—C4	1.444 (3)	C17—H17	0.9300
C3—C19	1.501 (2)	C18—H18	0.9300
C4—C5	1.402 (3)	C19—C20	1.511 (3)
C4—C9	1.400 (2)	C19—H19A	0.9700
C5—C6	1.372 (3)	C19—H19B	0.9700
C5—H5	0.9300	C20—C25	1.383 (3)
C6—C7	1.390 (3)	C20—C21	1.382 (3)
C6—H6	0.9300	C21—C22	1.383 (3)
C7—C8	1.379 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.362 (4)
C8—C9	1.393 (2)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.367 (4)
S10—O11	1.4271 (16)	C23—H23	0.9300
S10—O12	1.4275 (17)	C24—C25	1.390 (4)
S10—C13	1.754 (2)	C24—H24	0.9300
C13—C14	1.388 (3)	C25—H25	0.9300
C13—C18	1.379 (3)	C26—H26A	0.9600
C14—C15	1.382 (3)	C26—H26B	0.9600
C14—H14	0.9300	C26—H26C	0.9600
C9—N1—C2	107.81 (13)	C16—C15—H15	120.0
C9—N1—S10	122.63 (11)	C17—C16—C15	120.8 (2)
C2—N1—S10	123.53 (12)	C17—C16—H16	119.6
C3—C2—N1	108.62 (15)	C15—C16—H16	119.6
C3—C2—C26	127.39 (16)	C16—C17—C18	120.2 (2)
N1—C2—C26	123.76 (16)	C16—C17—H17	119.9
C2—C3—C4	108.66 (15)	C18—C17—H17	119.9
C2—C3—C19	125.53 (17)	C13—C18—C17	119.2 (2)
C4—C3—C19	125.81 (16)	C13—C18—H18	120.4
C5—C4—C9	119.39 (17)	C17—C18—H18	120.4
C5—C4—C3	132.68 (17)	C20—C19—C3	115.70 (14)
C9—C4—C3	107.92 (15)	C20—C19—H19A	108.4
C4—C5—C6	119.0 (2)	C3—C19—H19A	108.4
C4—C5—H5	120.5	C20—C19—H19B	108.4
C6—C5—H5	120.5	C3—C19—H19B	108.4
C7—C6—C5	120.7 (2)	H19A—C19—H19B	107.4
C7—C6—H6	119.6	C25—C20—C21	118.35 (19)
C5—C6—H6	119.6	C25—C20—C19	119.20 (18)
C6—C7—C8	121.84 (19)	C21—C20—C19	122.39 (17)
C6—C7—H7	119.1	C20—C21—C22	121.2 (2)
C8—C7—H7	119.1	C20—C21—H21	119.4
C7—C8—C9	117.39 (19)	C22—C21—H21	119.4
C7—C8—H8	121.3	C23—C22—C21	120.0 (2)
C9—C8—H8	121.3	C23—C22—H22	120.0
C4—C9—C8	121.63 (17)	C21—C22—H22	120.0
C4—C9—N1	106.95 (14)	C22—C23—C24	119.8 (2)
C8—C9—N1	131.34 (16)	C22—C23—H23	120.1
O11—S10—O12	119.73 (9)	C24—C23—H23	120.1
O11—S10—N1	105.81 (8)	C25—C24—C23	120.7 (2)
O12—S10—N1	107.20 (8)	C25—C24—H24	119.6
O11—S10—C13	108.89 (9)	C23—C24—H24	119.6
O12—S10—C13	108.73 (10)	C20—C25—C24	119.9 (2)
N1—S10—C13	105.57 (8)	C20—C25—H25	120.1
C14—C13—C18	120.5 (2)	C24—C25—H25	120.1
C14—C13—S10	119.83 (14)	C2—C26—H26A	109.5
C18—C13—S10	119.68 (17)	C2—C26—H26B	109.5
C13—C14—C15	119.3 (2)	H26A—C26—H26B	109.5
C13—C14—H14	120.3	C2—C26—H26C	109.5
C15—C14—H14	120.3	H26A—C26—H26C	109.5
C14—C15—C16	120.0 (2)	H26B—C26—H26C	109.5
C14—C15—H15	120.0
S10—N1—C2—C26	−30.4 (2)	C2—N1—S10—O12	41.93 (16)
S10—N1—C9—C8	28.1 (2)	C9—N1—S10—C13	75.43 (14)
S10—N1—C2—C3	154.71 (12)	C2—N1—S10—C13	−73.88 (15)
C9—N1—C2—C3	1.55 (18)	O11—S10—C13—C14	27.27 (17)
C9—N1—C2—C26	176.44 (17)	O12—S10—C13—C14	159.30 (15)
N1—C2—C3—C4	−0.95 (19)	N1—S10—C13—C14	−85.95 (16)
C26—C2—C3—C4	−175.60 (18)	O11—S10—C13—C18	−153.38 (17)
N1—C2—C3—C19	178.35 (15)	O12—S10—C13—C18	−21.35 (19)
C26—C2—C3—C19	3.7 (3)	N1—S10—C13—C18	93.40 (18)
C2—C3—C4—C5	178.93 (18)	C18—C13—C14—C15	−0.1 (3)
C19—C3—C4—C5	−0.4 (3)	S10—C13—C14—C15	179.26 (15)
C2—C3—C4—C9	−0.01 (18)	C13—C14—C15—C16	−0.4 (3)
C19—C3—C4—C9	−179.30 (15)	C14—C15—C16—C17	0.7 (4)
C9—C4—C5—C6	−0.2 (3)	C15—C16—C17—C18	−0.6 (4)
C3—C4—C5—C6	−179.08 (18)	C14—C13—C18—C17	0.2 (3)
C4—C5—C6—C7	0.9 (3)	S10—C13—C18—C17	−179.1 (2)
C5—C6—C7—C8	−0.5 (3)	C16—C17—C18—C13	0.1 (4)
C6—C7—C8—C9	−0.6 (3)	C2—C3—C19—C20	−86.5 (2)
C5—C4—C9—C8	−0.9 (2)	C4—C3—C19—C20	92.6 (2)
C3—C4—C9—C8	178.20 (15)	C3—C19—C20—C25	150.98 (19)
C5—C4—C9—N1	−178.15 (15)	C3—C19—C20—C21	−31.7 (3)
C3—C4—C9—N1	0.96 (17)	C25—C20—C21—C22	1.6 (3)
C7—C8—C9—C4	1.3 (3)	C19—C20—C21—C22	−175.7 (2)
C7—C8—C9—N1	177.79 (17)	C20—C21—C22—C23	−0.2 (4)
C2—N1—C9—C4	−1.52 (17)	C21—C22—C23—C24	−0.8 (4)
S10—N1—C9—C4	−154.97 (11)	C22—C23—C24—C25	0.3 (4)
C2—N1—C9—C8	−178.40 (18)	C21—C20—C25—C24	−2.1 (3)
C9—N1—S10—O11	−39.92 (14)	C19—C20—C25—C24	175.4 (2)
C2—N1—S10—O11	170.78 (13)	C23—C24—C25—C20	1.2 (4)
C9—N1—S10—O12	−168.76 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26A···O12	0.96	2.07	2.862 (3)	139
C16—H16···O11^i	0.93	2.56	3.399 (3)	151
C5—H5···Cg1^ii	0.93	3.09	4.018 (4)	173
C15—H15···Cg2^ii	0.93	3.05	3.701 (4)	129
C17—H17···Cg2^iii	0.93	3.27	3.953 (4)	132

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