2,3-Dibenz­yl-1-(phenyl­sulfon­yl)-1H-indole

In the crystal structure of the title compound, C₂₈H₂₃NO₂S, the two benzyl groups are rotated in a such a way as to minimize their mutual inter­actions and their inter­action with the phenyl­sulfonyl ring.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.099
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C28 H23 N O2 S

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

   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-NT (Bruker, 2006); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

2,3-(Dibenzyl)-1-(phenylsulfonyl)-1H-indole

Crystal data

C28H23NO2S	F(000) = 920
Mr = 437.56	Dx = 1.335 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.3830 (4) Å	Cell parameters from 8229 reflections
b = 15.6589 (6) Å	θ = 2.1–30.1°
c = 12.2180 (5) Å	µ = 0.18 mm^−1
β = 91.6083 (18)°	T = 120 K
V = 2176.94 (14) Å^3	Prism, colorless
Z = 4	0.38 × 0.36 × 0.34 mm

Data collection

Bruker–Nonius APEX2 diffractometer	4354 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 30.2°, θmin = 2.2°
Absorption correction: ψ scan (North et al., 1968)	h = −14→16
Tmin = 0.939, Tmax = 0.942	k = −22→21
27006 measured reflections	l = −17→17
6427 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	All H-atom parameters refined
wR(F^2) = 0.099	w = 1/[σ^2(F^2) + (0.04P)^2 + 0.72P], where P = [max(Fo^2,0) + 2Fc^2]/3
S = 1.05	(Δ/σ)max = 0.000227
4354 reflections	Δρmax = 0.72 e Å^−3
289 parameters	Δρmin = −0.39 e Å^−3
0 restraints

Special details

Experimental. ¹H NMR (CDCl₃): δ 8.37 (d, 1H, J = 8.1 Hz), 8.12 (d, 1H, J = 7.5 Hz), 8.03 (d, 1H, J = 7.2 Hz), 7.80–7.67 (m, 1H), 7.64 (d, 1H, J = 7.8 Hz), 7.57 (d, 1H, J = 7.2 Hz), 7.51–7.39 (m, 4H), 7.32–7.22 (m, 5H), 7.18–7.02 (m, 4H), 4.64 (s, 2H), 4.18 (s, 2H); ¹³C NMR (CDCl₃): δ 139.2, 138.8, 138.7,137.1, 136.2, 133.5, 130.8, 129.0 (3 C), 128.6 (4 C), 128.3 (2 C), 126.5 (3 C), 126.4 (2 C), 124.7, 123.8, 121.5, 119.5, 115.5, 31.7, 30.2; MS m/z: 437 (M⁺), 403, 347, 296, 206, 172, 141, 108, 91, 77 (100%); HRMS calculated for C₂₈H₂₃NO₂S: 437.1450; found: 437.1444.

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

	x	y	z	Uiso*/Ueq
S1	−0.30787 (4)	−0.11263 (3)	−0.28961 (4)	0.0196
O1	−0.27455 (11)	−0.19921 (8)	−0.26903 (11)	0.0257
O2	−0.25240 (11)	−0.06555 (8)	−0.37370 (10)	0.0246
N1	−0.28310 (12)	−0.06025 (9)	−0.17287 (12)	0.0192
C2	−0.28313 (14)	0.03125 (10)	−0.16253 (14)	0.0190
C3	−0.31453 (14)	0.05208 (11)	−0.05997 (15)	0.0202
C4	−0.34139 (14)	−0.02565 (11)	−0.00211 (14)	0.0204
C5	−0.38071 (15)	−0.04046 (13)	0.10313 (15)	0.0258
C6	−0.40085 (15)	−0.12369 (13)	0.13555 (15)	0.0283
C7	−0.38064 (15)	−0.19165 (13)	0.06498 (16)	0.0279
C8	−0.34066 (15)	−0.17889 (11)	−0.03998 (16)	0.0245
C9	−0.32243 (14)	−0.09445 (11)	−0.07244 (14)	0.0197
C10	−0.46078 (14)	−0.10877 (11)	−0.31324 (13)	0.0193
C11	−0.50927 (15)	−0.03863 (11)	−0.36800 (14)	0.0218
C12	−0.62983 (16)	−0.03550 (12)	−0.38744 (15)	0.0251
C13	−0.70030 (16)	−0.10122 (13)	−0.35121 (15)	0.0276
C14	−0.65166 (16)	−0.17100 (12)	−0.29690 (16)	0.0271
C15	−0.53104 (15)	−0.17572 (11)	−0.27757 (15)	0.0236
C16	−0.24507 (15)	0.09047 (11)	−0.25099 (15)	0.0223
C17	−0.11410 (15)	0.09175 (10)	−0.27065 (15)	0.0219
C18	−0.07261 (18)	0.09171 (13)	−0.37637 (17)	0.0324
C19	0.04741 (19)	0.09893 (14)	−0.39492 (19)	0.0387
C20	0.12659 (17)	0.10618 (13)	−0.30723 (18)	0.0329
C21	0.08642 (15)	0.10554 (12)	−0.20220 (17)	0.0279
C22	−0.03331 (15)	0.09790 (11)	−0.18333 (16)	0.0237
C23	−0.31824 (15)	0.13986 (11)	−0.00999 (16)	0.0243
C24	−0.20367 (14)	0.16750 (11)	0.04606 (14)	0.0201
C25	−0.16690 (16)	0.25142 (11)	0.03665 (15)	0.0243
C26	−0.06081 (18)	0.27786 (13)	0.08390 (17)	0.0330
C27	0.00937 (17)	0.22078 (13)	0.14314 (17)	0.0322
C28	−0.02813 (17)	0.13770 (13)	0.15508 (17)	0.0309
C29	−0.13339 (16)	0.11103 (12)	0.10623 (17)	0.0286
H51	−0.3943	0.0084	0.1539	0.0317*
H61	−0.4295	−0.1352	0.2107	0.0355*
H71	−0.3961	−0.2512	0.0904	0.0340*
H81	−0.3247	−0.2278	−0.0901	0.0303*
H111	−0.4576	0.0089	−0.3927	0.0276*
H121	−0.6660	0.0140	−0.4277	0.0304*
H131	−0.7873	−0.0981	−0.3643	0.0345*
H141	−0.7037	−0.2181	−0.2717	0.0336*
H151	−0.4949	−0.2260	−0.2389	0.0290*
H161	−0.2859	0.0725	−0.3207	0.0279*
H162	−0.2702	0.1497	−0.2317	0.0279*
H181	−0.1297	0.0869	−0.4398	0.0401*
H191	0.0766	0.0984	−0.4714	0.0474*
H201	0.2126	0.1118	−0.3203	0.0399*
H211	0.1437	0.1108	−0.1390	0.0353*
H221	−0.0621	0.0969	−0.1067	0.0298*
H231	−0.3811	0.1405	0.0455	0.0316*
H232	−0.3381	0.1819	−0.0693	0.0316*
H251	−0.2170	0.2934	−0.0050	0.0296*
H261	−0.0351	0.3386	0.0763	0.0405*
H271	0.0868	0.2397	0.1754	0.0392*
H281	0.0205	0.0966	0.1996	0.0369*
H291	−0.1594	0.0504	0.1144	0.0352*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01882 (19)	0.01720 (19)	0.0227 (2)	0.00168 (15)	−0.00212 (14)	−0.00121 (16)
O1	0.0260 (6)	0.0180 (6)	0.0328 (7)	0.0050 (5)	−0.0038 (5)	−0.0024 (5)
O2	0.0231 (6)	0.0254 (7)	0.0253 (6)	0.0000 (5)	0.0027 (5)	−0.0002 (5)
N1	0.0201 (7)	0.0165 (7)	0.0210 (7)	−0.0001 (5)	−0.0024 (5)	0.0002 (5)
C2	0.0141 (7)	0.0157 (7)	0.0269 (9)	0.0004 (6)	−0.0037 (6)	0.0005 (6)
C3	0.0140 (7)	0.0199 (8)	0.0263 (9)	0.0013 (6)	−0.0039 (6)	−0.0008 (7)
C4	0.0131 (7)	0.0237 (8)	0.0242 (8)	0.0003 (6)	−0.0048 (6)	−0.0002 (7)
C5	0.0184 (8)	0.0348 (10)	0.0240 (9)	0.0008 (7)	−0.0029 (7)	−0.0002 (8)
C6	0.0192 (8)	0.0417 (12)	0.0238 (9)	−0.0029 (7)	−0.0026 (7)	0.0077 (8)
C7	0.0214 (9)	0.0294 (10)	0.0326 (10)	−0.0035 (7)	−0.0062 (7)	0.0101 (8)
C8	0.0227 (8)	0.0206 (8)	0.0298 (9)	−0.0018 (7)	−0.0058 (7)	0.0038 (7)
C9	0.0147 (7)	0.0217 (9)	0.0224 (8)	−0.0006 (6)	−0.0038 (6)	0.0020 (6)
C10	0.0191 (7)	0.0182 (8)	0.0205 (8)	0.0012 (6)	−0.0023 (6)	−0.0032 (7)
C11	0.0222 (8)	0.0215 (8)	0.0215 (8)	0.0012 (6)	0.0001 (6)	0.0011 (7)
C12	0.0244 (9)	0.0282 (9)	0.0224 (9)	0.0061 (7)	−0.0028 (7)	0.0002 (7)
C13	0.0210 (8)	0.0339 (10)	0.0276 (9)	0.0012 (7)	−0.0052 (7)	−0.0023 (8)
C14	0.0242 (9)	0.0258 (9)	0.0310 (10)	−0.0058 (7)	−0.0041 (7)	−0.0008 (8)
C15	0.0257 (8)	0.0188 (8)	0.0261 (9)	−0.0014 (7)	−0.0059 (7)	−0.0007 (7)
C16	0.0193 (8)	0.0182 (8)	0.0293 (9)	−0.0008 (6)	−0.0031 (7)	0.0041 (7)
C17	0.0205 (8)	0.0148 (8)	0.0305 (9)	−0.0003 (6)	0.0002 (7)	0.0030 (7)
C18	0.0309 (10)	0.0355 (11)	0.0309 (10)	−0.0044 (8)	0.0004 (8)	0.0010 (8)
C19	0.0363 (11)	0.0428 (13)	0.0378 (12)	−0.0055 (9)	0.0142 (9)	−0.0036 (10)
C20	0.0227 (9)	0.0266 (10)	0.0500 (12)	−0.0005 (7)	0.0097 (8)	−0.0014 (9)
C21	0.0201 (8)	0.0220 (9)	0.0415 (11)	0.0018 (7)	−0.0007 (7)	0.0035 (8)
C22	0.0200 (8)	0.0199 (9)	0.0312 (9)	0.0003 (6)	0.0002 (7)	0.0032 (7)
C23	0.0198 (8)	0.0214 (8)	0.0313 (10)	0.0034 (6)	−0.0047 (7)	−0.0048 (7)
C24	0.0190 (8)	0.0211 (8)	0.0202 (8)	0.0022 (6)	−0.0008 (6)	−0.0043 (6)
C25	0.0308 (9)	0.0210 (8)	0.0210 (8)	0.0015 (7)	−0.0023 (7)	−0.0006 (7)
C26	0.0381 (11)	0.0216 (9)	0.0389 (11)	−0.0068 (8)	−0.0093 (9)	−0.0008 (8)
C27	0.0255 (9)	0.0314 (10)	0.0392 (11)	−0.0033 (8)	−0.0095 (8)	−0.0066 (9)
C28	0.0267 (9)	0.0267 (10)	0.0388 (11)	0.0036 (7)	−0.0093 (8)	0.0002 (8)
C29	0.0240 (9)	0.0202 (9)	0.0412 (11)	−0.0005 (7)	−0.0081 (8)	0.0030 (8)

Geometric parameters (Å, º)

S1—O1	1.4282 (13)	C15—H151	1.000
S1—O2	1.4263 (13)	C16—C17	1.517 (2)
S1—N1	1.6626 (15)	C16—H161	1.000
S1—C10	1.7574 (16)	C16—H162	1.000
N1—C2	1.438 (2)	C17—C18	1.388 (3)
N1—C9	1.423 (2)	C17—C22	1.392 (2)
C2—C3	1.353 (2)	C18—C19	1.396 (3)
C2—C16	1.497 (2)	C18—H181	1.000
C3—C4	1.445 (2)	C19—C20	1.385 (3)
C3—C23	1.505 (2)	C19—H191	1.000
C4—C5	1.393 (3)	C20—C21	1.374 (3)
C4—C9	1.399 (2)	C20—H201	1.000
C5—C6	1.383 (3)	C21—C22	1.394 (2)
C5—H51	1.000	C21—H211	1.000
C6—C7	1.393 (3)	C22—H221	1.000
C6—H61	1.000	C23—C24	1.519 (2)
C7—C8	1.387 (3)	C23—H231	1.000
C7—H71	1.000	C23—H232	1.000
C8—C9	1.398 (2)	C24—C25	1.385 (2)
C8—H81	1.000	C24—C29	1.389 (2)
C10—C11	1.392 (2)	C25—C26	1.387 (3)
C10—C15	1.396 (2)	C25—H251	1.000
C11—C12	1.387 (2)	C26—C27	1.389 (3)
C11—H111	1.000	C26—H261	1.000
C12—C13	1.385 (3)	C27—C28	1.378 (3)
C12—H121	1.000	C27—H271	1.000
C13—C14	1.386 (3)	C28—C29	1.388 (2)
C13—H131	1.000	C28—H281	1.000
C14—C15	1.389 (2)	C29—H291	1.000
C14—H141	1.000
O1—S1—O2	119.79 (8)	C14—C15—H151	120.9
O1—S1—N1	106.23 (7)	C2—C16—C17	115.35 (14)
O2—S1—N1	107.17 (7)	C2—C16—H161	107.7
O1—S1—C10	108.57 (8)	C17—C16—H161	107.7
O2—S1—C10	108.68 (8)	C2—C16—H162	108.3
N1—S1—C10	105.50 (7)	C17—C16—H162	108.3
S1—N1—C2	124.50 (12)	H161—C16—H162	109.5
S1—N1—C9	120.28 (11)	C16—C17—C18	120.60 (16)
C2—N1—C9	107.36 (13)	C16—C17—C22	120.71 (16)
N1—C2—C3	108.80 (15)	C18—C17—C22	118.59 (16)
N1—C2—C16	123.55 (15)	C17—C18—C19	120.76 (19)
C3—C2—C16	127.50 (16)	C17—C18—H181	119.3
C2—C3—C4	108.38 (15)	C19—C18—H181	119.9
C2—C3—C23	127.39 (16)	C18—C19—C20	119.97 (19)
C4—C3—C23	124.21 (16)	C18—C19—H191	120.2
C3—C4—C5	132.07 (17)	C20—C19—H191	119.8
C3—C4—C9	108.06 (15)	C19—C20—C21	119.69 (17)
C5—C4—C9	119.87 (16)	C19—C20—H201	120.1
C4—C5—C6	118.78 (18)	C21—C20—H201	120.2
C4—C5—H51	120.3	C20—C21—C22	120.50 (18)
C6—C5—H51	120.9	C20—C21—H211	119.6
C5—C6—C7	120.73 (18)	C22—C21—H211	119.9
C5—C6—H61	119.6	C21—C22—C17	120.48 (18)
C7—C6—H61	119.7	C21—C22—H221	120.2
C6—C7—C8	121.77 (17)	C17—C22—H221	119.3
C6—C7—H71	119.1	C3—C23—C24	114.19 (14)
C8—C7—H71	119.1	C3—C23—H231	108.2
C7—C8—C9	116.98 (17)	C24—C23—H231	108.3
C7—C8—H81	121.7	C3—C23—H232	108.4
C9—C8—H81	121.3	C24—C23—H232	108.2
N1—C9—C4	107.31 (14)	H231—C23—H232	109.5
N1—C9—C8	130.83 (16)	C23—C24—C25	119.39 (15)
C4—C9—C8	121.85 (17)	C23—C24—C29	122.12 (16)
S1—C10—C11	118.92 (13)	C25—C24—C29	118.49 (16)
S1—C10—C15	119.76 (13)	C24—C25—C26	120.69 (17)
C11—C10—C15	121.32 (15)	C24—C25—H251	119.7
C10—C11—C12	119.15 (16)	C26—C25—H251	119.6
C10—C11—H111	120.2	C25—C26—C27	120.40 (18)
C12—C11—H111	120.6	C25—C26—H261	119.9
C11—C12—C13	119.88 (17)	C27—C26—H261	119.7
C11—C12—H121	120.2	C26—C27—C28	119.17 (17)
C13—C12—H121	119.9	C26—C27—H271	120.2
C12—C13—C14	120.78 (17)	C28—C27—H271	120.6
C12—C13—H131	119.5	C27—C28—C29	120.31 (18)
C14—C13—H131	119.7	C27—C28—H281	119.8
C13—C14—C15	120.22 (17)	C29—C28—H281	119.9
C13—C14—H141	119.8	C24—C29—C28	120.90 (17)
C15—C14—H141	120.0	C24—C29—H291	119.3
C10—C15—C14	118.64 (16)	C28—C29—H291	119.8
C10—C15—H151	120.5