2,3-Diphenyl-1-(phenyl­sulfon­yl)indole

The crystal structure of the title compound, C₂₆H₁₉NO₂S, reveals that the phenyl­sulfonyl ring and the adjacent phenyl ring are approximately syn-parallel to each other, with a dihedral angle of 18.4 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.051
• wR factor = 0.264
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.80
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         21 Perc.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.89

Alert level B
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C22    -C27           1.36 Ang.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         16

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.264
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT084_ALERT_2_C High R2 Value ..................................       0.26
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C22    -   C23     ..       5.88 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               3716
           From the CIF: _diffrn_reflns_limit_ max hkl   12.   19.   14.
           From the CIF: _diffrn_reflns_limit_ min hkl    0.    0.  -15.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   15.   19.   15.
           Calculated minimum hkl  -15.  -19.  -15.

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

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

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

2,3-Diphenyl-1-(phenylsulfonyl)indole

Crystal data

C26H19NO2S	F(000) = 856
Mr = 409.48	Dx = 1.339 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 12 reflections
a = 11.768 (6) Å	θ = 6.2–11.2°
b = 15.198 (4) Å	µ = 0.18 mm^−1
c = 12.223 (7) Å	T = 296 K
β = 111.71 (3)°	Plate, colorless
V = 2030.9 (16) Å^3	0.40 × 0.40 × 0.10 mm
Z = 4

Data collection

Rigaku AFC-6S diffractometer	789 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 1.9°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→19
Tmin = 0.931, Tmax = 0.982	l = −15→14
3716 measured reflections	3 standard reflections every 150 reflections
3716 independent reflections	intensity decay: none

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.264	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0942P)^2] where P = (Fo^2 + 2Fc^2)/3
3716 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Experimental. IR (KBr, ν_max, cm^-1): 1446, 1356, 1176, 1086; ¹H NMR (CDCl₃, δ, p.p.m.): 8.43 (m, 1H), 7.51–7.41 (m, 5H), 7.36–7.21 (m, 11H), 7.11–7.07 (m, 2H); ¹³C NMR (CDCl₃, δ, p.p.m.): 138.4, 137.5, 137.0, 133.7, 132.8, 132.3, 131.0, 130.7, 130.0, 128.9, 128.7, 128.4, 127.5, 127.2, 127.1, 125.5, 125.1, 124.5, 120.2, 116.5; HRMS, m/z calculated for C₂₆H₁₉NO₂S (M⁺) 409.1137, found 409.1138. Analysis, calculated for C₂₆H₁₉NO₂S: C 76.26, H 4.68, N 3.42, S 7.83%; found: C 76.34, H 4.73, N 3.50, S 7.82%.

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
S1	0.4241 (2)	0.03770 (18)	0.7128 (2)	0.0490 (8)
O2	0.4890 (6)	0.0328 (5)	0.8367 (5)	0.069 (2)
O1	0.4321 (6)	−0.0337 (4)	0.6405 (5)	0.0572 (19)
N1	0.2760 (6)	0.0514 (5)	0.6941 (6)	0.046 (2)
C2	0.1874 (8)	0.0913 (6)	0.5912 (7)	0.039 (2)
C3	0.0899 (8)	0.1176 (6)	0.6157 (8)	0.042 (3)
C4	0.1111 (9)	0.0941 (6)	0.7357 (7)	0.039 (2)
C5	0.0439 (10)	0.1038 (7)	0.8075 (10)	0.062 (3)
H7	−0.0322	0.1310	0.7784	0.074*
C6	0.0887 (11)	0.0737 (7)	0.9190 (11)	0.070 (3)
H19	0.0422	0.0795	0.9657	0.084*
C7	0.2025 (12)	0.0344 (7)	0.9653 (8)	0.065 (3)
H10	0.2310	0.0137	1.0424	0.079*
C8	0.2749 (10)	0.0253 (7)	0.8986 (8)	0.061 (3)
H3	0.3524	0.0001	0.9294	0.073*
C9	0.2259 (9)	0.0557 (6)	0.7835 (8)	0.044 (3)
C10	0.4637 (8)	0.1359 (6)	0.6617 (7)	0.040 (2)
C11	0.5122 (8)	0.1300 (7)	0.5736 (8)	0.053 (3)
H5	0.5218	0.0756	0.5432	0.063*
C12	0.5454 (11)	0.2058 (9)	0.5328 (10)	0.077 (4)
H18	0.5807	0.2027	0.4762	0.092*
C13	0.5275 (11)	0.2851 (10)	0.5741 (12)	0.086 (4)
H16	0.5497	0.3360	0.5448	0.103*
C14	0.4771 (11)	0.2914 (7)	0.6584 (12)	0.080 (4)
H11	0.4634	0.3465	0.6844	0.096*
C15	0.4468 (10)	0.2168 (8)	0.7048 (8)	0.063 (3)
H9	0.4155	0.2206	0.7642	0.075*
C16	0.2066 (8)	0.0961 (6)	0.4784 (7)	0.038 (2)
C17	0.2212 (8)	0.0235 (7)	0.4172 (8)	0.054 (3)
H2	0.2229	−0.0322	0.4494	0.064*
C18	0.2332 (9)	0.0310 (8)	0.3102 (9)	0.064 (3)
H13	0.2428	−0.0189	0.2705	0.077*
C19	0.2309 (9)	0.1129 (9)	0.2624 (9)	0.066 (3)
H12	0.2384	0.1187	0.1897	0.079*
C20	0.2173 (8)	0.1868 (7)	0.3223 (9)	0.054 (3)
H4	0.2167	0.2422	0.2898	0.065*
C21	0.2045 (8)	0.1795 (6)	0.4296 (8)	0.047 (3)
H1	0.1946	0.2295	0.4690	0.057*
C22	−0.0213 (8)	0.1630 (6)	0.5334 (8)	0.033 (2)
C23	−0.0743 (9)	0.1368 (7)	0.4244 (10)	0.059 (3)
H8	−0.0452	0.0862	0.4009	0.071*
C24	−0.1697 (12)	0.1797 (10)	0.3438 (12)	0.088 (4)
H15	−0.2048	0.1589	0.2670	0.106*
C25	−0.2140 (11)	0.2555 (11)	0.3783 (13)	0.095 (5)
H17	−0.2793	0.2867	0.3254	0.114*
C26	−0.1574 (11)	0.2830 (8)	0.4943 (13)	0.084 (4)
H14	−0.1849	0.3333	0.5201	0.101*
C27	−0.0615 (10)	0.2366 (8)	0.5707 (10)	0.070 (3)
H6	−0.0238	0.2554	0.6482	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0513 (17)	0.0502 (17)	0.0434 (15)	0.0153 (16)	0.0152 (13)	0.0097 (16)
O2	0.068 (5)	0.087 (5)	0.047 (4)	0.019 (5)	0.016 (4)	0.019 (4)
O1	0.079 (5)	0.036 (4)	0.074 (4)	0.019 (4)	0.048 (4)	0.009 (4)
N1	0.045 (5)	0.048 (5)	0.045 (5)	0.011 (4)	0.016 (4)	0.004 (4)
C2	0.044 (7)	0.032 (6)	0.038 (6)	−0.001 (5)	0.010 (5)	0.004 (5)
C3	0.037 (6)	0.043 (6)	0.051 (6)	−0.013 (5)	0.022 (5)	−0.005 (5)
C4	0.044 (7)	0.038 (6)	0.039 (6)	−0.002 (5)	0.019 (5)	−0.002 (5)
C5	0.070 (8)	0.061 (8)	0.064 (7)	0.000 (6)	0.034 (7)	−0.004 (6)
C6	0.075 (9)	0.068 (9)	0.084 (10)	−0.010 (7)	0.051 (8)	−0.007 (7)
C7	0.109 (10)	0.059 (7)	0.041 (6)	−0.014 (8)	0.043 (7)	−0.002 (6)
C8	0.082 (8)	0.055 (7)	0.044 (6)	−0.003 (6)	0.022 (6)	−0.006 (6)
C9	0.065 (7)	0.040 (7)	0.039 (6)	−0.008 (6)	0.033 (5)	0.000 (5)
C10	0.042 (6)	0.045 (6)	0.029 (5)	0.001 (5)	0.009 (5)	−0.003 (5)
C11	0.054 (7)	0.037 (6)	0.064 (7)	0.001 (6)	0.018 (6)	0.003 (6)
C12	0.090 (10)	0.062 (8)	0.078 (9)	−0.012 (8)	0.030 (8)	−0.022 (8)
C13	0.063 (9)	0.098 (13)	0.093 (10)	−0.023 (8)	0.024 (8)	0.011 (9)
C14	0.082 (9)	0.021 (7)	0.116 (11)	−0.010 (6)	0.015 (8)	−0.022 (7)
C15	0.074 (8)	0.062 (8)	0.045 (6)	−0.001 (7)	0.013 (6)	−0.030 (7)
C16	0.044 (6)	0.039 (6)	0.033 (5)	−0.001 (5)	0.016 (5)	0.006 (5)
C17	0.055 (7)	0.067 (8)	0.045 (6)	−0.008 (6)	0.025 (5)	−0.009 (6)
C18	0.070 (8)	0.060 (8)	0.066 (7)	0.005 (7)	0.028 (6)	−0.010 (7)
C19	0.072 (8)	0.084 (9)	0.050 (7)	0.006 (7)	0.031 (6)	−0.004 (7)
C20	0.057 (7)	0.046 (7)	0.066 (7)	0.006 (6)	0.029 (6)	0.026 (6)
C21	0.048 (7)	0.047 (7)	0.049 (6)	0.007 (5)	0.019 (5)	0.008 (5)
C22	0.034 (6)	0.033 (6)	0.035 (6)	−0.011 (5)	0.015 (5)	−0.005 (5)
C23	0.034 (7)	0.045 (7)	0.087 (9)	0.010 (6)	0.010 (6)	0.018 (7)
C24	0.067 (10)	0.102 (11)	0.089 (10)	0.014 (9)	0.021 (8)	0.009 (9)
C25	0.044 (8)	0.124 (14)	0.103 (12)	0.006 (9)	0.010 (8)	0.060 (11)
C26	0.065 (9)	0.071 (9)	0.112 (11)	0.010 (8)	0.027 (8)	0.000 (9)
C27	0.060 (8)	0.073 (9)	0.070 (8)	0.011 (7)	0.016 (7)	0.013 (7)

Geometric parameters (Å, º)

S1—O2	1.423 (6)	C13—H16	0.9300
S1—O1	1.424 (6)	C14—C15	1.372 (14)
S1—N1	1.685 (7)	C14—H11	0.9300
S1—C10	1.746 (10)	C15—H9	0.9300
N1—C9	1.422 (10)	C16—C17	1.380 (12)
N1—C2	1.437 (10)	C16—C21	1.397 (11)
C2—C3	1.349 (11)	C17—C18	1.371 (12)
C2—C16	1.479 (11)	C17—H2	0.9300
C3—C4	1.439 (11)	C18—C19	1.370 (14)
C3—C22	1.492 (12)	C18—H13	0.9300
C4—C9	1.386 (12)	C19—C20	1.382 (14)
C4—C5	1.389 (12)	C19—H12	0.9300
C5—C6	1.347 (13)	C20—C21	1.379 (12)
C5—H7	0.9300	C20—H4	0.9300
C6—C7	1.383 (14)	C21—H1	0.9300
C6—H19	0.9300	C22—C23	1.307 (12)
C7—C8	1.387 (13)	C22—C27	1.358 (12)
C7—H10	0.9300	C23—C24	1.355 (14)
C8—C9	1.388 (12)	C23—H8	0.9300
C8—H3	0.9300	C24—C25	1.393 (16)
C10—C15	1.381 (12)	C24—H15	0.9300
C10—C11	1.396 (12)	C25—C26	1.390 (15)
C11—C12	1.368 (14)	C25—H17	0.9300
C11—H5	0.9300	C26—C27	1.364 (14)
C12—C13	1.353 (15)	C26—H14	0.9300
C12—H18	0.9300	C27—H6	0.9300
C13—C14	1.369 (16)
O2—S1—O1	119.2 (4)	C14—C13—H16	119.5
O2—S1—N1	105.8 (4)	C13—C14—C15	120.2 (11)
O1—S1—N1	108.2 (4)	C13—C14—H11	119.9
O2—S1—C10	108.4 (4)	C15—C14—H11	119.9
O1—S1—C10	110.0 (4)	C14—C15—C10	118.8 (10)
N1—S1—C10	104.2 (4)	C14—C15—H9	120.6
C9—N1—C2	106.3 (7)	C10—C15—H9	120.6
C9—N1—S1	127.1 (6)	C17—C16—C21	118.7 (9)
C2—N1—S1	123.4 (6)	C17—C16—C2	124.0 (9)
C3—C2—N1	109.4 (8)	C21—C16—C2	117.3 (9)
C3—C2—C16	128.9 (8)	C18—C17—C16	121.9 (11)
N1—C2—C16	121.7 (8)	C18—C17—H2	119.1
C2—C3—C4	108.2 (8)	C16—C17—H2	119.1
C2—C3—C22	126.4 (8)	C19—C18—C17	119.3 (11)
C4—C3—C22	125.5 (8)	C19—C18—H13	120.3
C9—C4—C5	118.1 (9)	C17—C18—H13	120.3
C9—C4—C3	108.0 (8)	C18—C19—C20	120.0 (10)
C5—C4—C3	133.9 (10)	C18—C19—H12	120.0
C6—C5—C4	120.2 (11)	C20—C19—H12	120.0
C6—C5—H7	119.9	C21—C20—C19	120.9 (10)
C4—C5—H7	119.9	C21—C20—H4	119.6
C5—C6—C7	121.2 (11)	C19—C20—H4	119.6
C5—C6—H19	119.4	C20—C21—C16	119.2 (9)
C7—C6—H19	119.4	C20—C21—H1	120.4
C6—C7—C8	121.0 (10)	C16—C21—H1	120.4
C6—C7—H10	119.5	C23—C22—C27	119.9 (10)
C8—C7—H10	119.5	C23—C22—C3	121.1 (9)
C7—C8—C9	116.6 (10)	C27—C22—C3	118.8 (9)
C7—C8—H3	121.7	C22—C23—C24	123.4 (11)
C9—C8—H3	121.7	C22—C23—H8	118.3
C4—C9—C8	122.9 (9)	C24—C23—H8	118.3
C4—C9—N1	108.2 (8)	C23—C24—C25	118.7 (13)
C8—C9—N1	128.9 (10)	C23—C24—H15	120.7
C15—C10—C11	120.6 (10)	C25—C24—H15	120.7
C15—C10—S1	122.0 (8)	C26—C25—C24	117.7 (13)
C11—C10—S1	117.4 (8)	C26—C25—H17	121.1
C12—C11—C10	118.7 (11)	C24—C25—H17	121.1
C12—C11—H5	120.7	C27—C26—C25	120.4 (13)
C10—C11—H5	120.7	C27—C26—H14	119.8
C13—C12—C11	120.6 (12)	C25—C26—H14	119.8
C13—C12—H18	119.7	C22—C27—C26	120.0 (11)
C11—C12—H18	119.7	C22—C27—H6	120.0
C12—C13—C14	120.9 (13)	C26—C27—H6	120.0
C12—C13—H16	119.5