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

In the title compound, C₁₄H₉I₂NO₂S, the two I atoms lie essentially in the plane of the indole ring and there is some iodine-iodine repulsion.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.032
• wR factor = 0.082
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  I2     ..  O2      ..       3.13 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H9 I2 N O2 S

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS.

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

Crystal data

C14H9I2NO2S	F(000) = 952
Mr = 509.11	Dx = 2.289 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.4680 (15) Å	Cell parameters from 3872 reflections
b = 11.9852 (18) Å	θ = 2–28°
c = 12.4945 (19) Å	µ = 4.40 mm^−1
β = 109.550 (3)°	T = 100 K
V = 1477.2 (4) Å^3	Prism, violet
Z = 4	0.50 × 0.26 × 0.12 mm

Data collection

Bruker-Nonius Kappa Apex2 diffractometer	2422 reflections with I > 3.0σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997)	h = −13→7
Tmin = 0.250, Tmax = 0.590	k = −15→15
9300 measured reflections	l = −16→15
3407 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.033	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(δF/6σF)^2]^2 Ai are: 37.8 38.0 29.3
wR(F^2) = 0.082	(Δ/σ)max = 0.000294
S = 0.95	Δρmax = 0.72 e Å^−3
2422 reflections	Δρmin = −1.53 e Å^−3
182 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 6.2 (16)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. ¹H NMR (CDCl₃): δ 8.29 (d, 1H, J = 7.2 Hz), 7.91 (d, 2H, J = 7.2 Hz), 7.59–7.52 (m, 2H), 7.45 (t, 2H,J = 8.1 Hz), 7.38–7.29 (m, 2H).

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

	x	y	z	Uiso*/Ueq
I1	0.49622 (4)	−0.39233 (3)	−0.16730 (3)	0.0291
I2	0.47619 (4)	−0.26347 (3)	0.10451 (3)	0.0223
S1	0.68870 (13)	−0.17522 (11)	−0.25869 (12)	0.0201
O1	0.6491 (5)	−0.2816 (4)	−0.3115 (4)	0.0285
O2	0.8175 (4)	−0.1295 (4)	−0.2492 (4)	0.0262
N1	0.6893 (5)	−0.1874 (4)	−0.1240 (4)	0.0186
C2	0.5936 (5)	−0.2494 (4)	−0.0905 (5)	0.0189
C3	0.5822 (5)	−0.2014 (4)	0.0056 (4)	0.0172
C4	0.6636 (5)	−0.1028 (5)	0.0312 (5)	0.0185
C5	0.6816 (6)	−0.0219 (5)	0.1145 (5)	0.0228
C6	0.7682 (6)	0.0667 (5)	0.1172 (5)	0.0270
C7	0.8357 (6)	0.0727 (5)	0.0384 (5)	0.0288
C8	0.8177 (6)	−0.0058 (5)	−0.0466 (5)	0.0240
C9	0.7305 (5)	−0.0942 (4)	−0.0492 (4)	0.0177
C10	0.5618 (6)	−0.0773 (5)	−0.3211 (4)	0.0228
C11	0.4266 (6)	−0.1115 (6)	−0.3559 (5)	0.0274
C12	0.3269 (7)	−0.0321 (6)	−0.4029 (5)	0.0339
C13	0.3621 (7)	0.0771 (6)	−0.4131 (5)	0.0381
C14	0.4958 (7)	0.1095 (6)	−0.3790 (5)	0.0323
C15	0.5975 (6)	0.0328 (5)	−0.3304 (5)	0.0257
H51	0.6340	−0.0277	0.1716	0.0245*
H61	0.7820	0.1265	0.1758	0.0279*
H71	0.8993	0.1363	0.0433	0.0297*
H81	0.8654	0.0000	−0.1036	0.0255*
H111	0.4025	−0.1911	−0.3483	0.0331*
H121	0.2292	−0.0544	−0.4282	0.0395*
H131	0.2893	0.1336	−0.4466	0.0417*
H141	0.5195	0.1889	−0.3885	0.0376*
H151	0.6949	0.0560	−0.3034	0.0306*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0370 (2)	0.0250 (2)	0.0280 (2)	−0.01307 (16)	0.01432 (17)	−0.00940 (14)
I2	0.02195 (19)	0.0288 (2)	0.01647 (19)	−0.00128 (13)	0.00690 (14)	0.00209 (13)
S1	0.0239 (6)	0.0210 (6)	0.0183 (6)	0.0011 (5)	0.0107 (5)	−0.0017 (5)
O1	0.040 (2)	0.024 (2)	0.025 (2)	−0.0065 (18)	0.0164 (19)	−0.0089 (17)
O2	0.023 (2)	0.029 (2)	0.032 (2)	0.0018 (16)	0.0161 (18)	0.0018 (18)
N1	0.021 (2)	0.021 (2)	0.013 (2)	−0.0023 (17)	0.0056 (17)	−0.0007 (16)
C2	0.019 (2)	0.016 (2)	0.018 (3)	−0.0010 (19)	0.002 (2)	0.0010 (19)
C3	0.017 (2)	0.022 (3)	0.011 (2)	−0.002 (2)	0.0032 (19)	0.0000 (18)
C4	0.015 (2)	0.020 (3)	0.016 (2)	0.003 (2)	0.0001 (19)	0.0027 (19)
C5	0.021 (3)	0.026 (3)	0.016 (2)	0.004 (2)	−0.001 (2)	0.000 (2)
C6	0.031 (3)	0.024 (3)	0.017 (3)	0.007 (2)	−0.004 (2)	−0.003 (2)
C7	0.030 (3)	0.022 (3)	0.027 (3)	−0.002 (2)	0.000 (2)	−0.001 (2)
C8	0.022 (3)	0.026 (3)	0.020 (3)	−0.002 (2)	0.001 (2)	0.000 (2)
C9	0.014 (2)	0.020 (2)	0.016 (2)	0.0008 (19)	−0.0002 (19)	−0.0004 (19)
C10	0.028 (3)	0.030 (3)	0.013 (2)	0.004 (2)	0.011 (2)	−0.002 (2)
C11	0.027 (3)	0.037 (3)	0.017 (3)	−0.006 (2)	0.007 (2)	−0.004 (2)
C12	0.027 (3)	0.051 (4)	0.019 (3)	0.003 (3)	0.001 (2)	−0.006 (3)
C13	0.039 (4)	0.050 (4)	0.019 (3)	0.021 (3)	0.003 (3)	0.004 (3)
C14	0.043 (4)	0.035 (4)	0.016 (3)	0.016 (3)	0.006 (3)	0.003 (2)
C15	0.031 (3)	0.028 (3)	0.016 (3)	0.003 (2)	0.005 (2)	0.001 (2)

Geometric parameters (Å, º)

I1—C2	2.059 (5)	C7—C8	1.384 (8)
I2—C3	2.057 (5)	C7—H71	1.000
S1—O1	1.432 (4)	C8—C9	1.392 (8)
S1—O2	1.423 (4)	C8—H81	1.000
S1—N1	1.688 (5)	C10—C11	1.396 (8)
S1—C10	1.748 (6)	C10—C15	1.387 (9)
N1—C2	1.418 (7)	C11—C12	1.389 (9)
N1—C9	1.427 (7)	C11—H111	1.000
C2—C3	1.371 (7)	C12—C13	1.378 (11)
C3—C4	1.429 (7)	C12—H121	1.000
C4—C5	1.389 (8)	C13—C14	1.376 (10)
C4—C9	1.407 (7)	C13—H131	1.000
C5—C6	1.390 (9)	C14—C15	1.384 (9)
C5—H51	1.000	C14—H141	1.000
C6—C7	1.393 (9)	C15—H151	1.000
C6—H61	1.000
O1—S1—O2	120.1 (3)	C8—C7—H71	118.9
O1—S1—N1	106.6 (2)	C7—C8—C9	117.1 (5)
O2—S1—N1	105.3 (2)	C7—C8—H81	121.8
O1—S1—C10	109.4 (3)	C9—C8—H81	121.0
O2—S1—C10	109.6 (3)	N1—C9—C4	107.2 (4)
N1—S1—C10	104.6 (2)	N1—C9—C8	131.6 (5)
S1—N1—C2	124.9 (4)	C4—C9—C8	121.2 (5)
S1—N1—C9	119.0 (4)	S1—C10—C11	118.8 (5)
C2—N1—C9	107.8 (4)	S1—C10—C15	119.4 (4)
N1—C2—I1	125.9 (4)	C11—C10—C15	121.8 (5)
N1—C2—C3	108.4 (4)	C10—C11—C12	118.1 (6)
I1—C2—C3	125.6 (4)	C10—C11—H111	120.8
C2—C3—I2	126.6 (4)	C12—C11—H111	121.1
C2—C3—C4	108.8 (5)	C11—C12—C13	120.2 (6)
I2—C3—C4	124.4 (4)	C11—C12—H121	119.7
C3—C4—C5	131.8 (5)	C13—C12—H121	120.1
C3—C4—C9	107.6 (5)	C12—C13—C14	121.0 (6)
C5—C4—C9	120.6 (5)	C12—C13—H131	119.5
C4—C5—C6	118.4 (5)	C14—C13—H131	119.5
C4—C5—H51	120.8	C13—C14—C15	120.2 (7)
C6—C5—H51	120.8	C13—C14—H141	119.9
C5—C6—C7	120.2 (5)	C15—C14—H141	119.9
C5—C6—H61	119.9	C10—C15—C14	118.7 (6)
C7—C6—H61	119.9	C10—C15—H151	120.6
C6—C7—C8	122.4 (6)	C14—C15—H151	120.8
C6—C7—H71	118.7