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In the title compound, C14H10N2O4S, the nitro group, confirmed as being in the 6-position, is coplanar with the indole ring system and the angle between the planes of the indole system and the phenyl ring is 96.1 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048616/tk2100sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048616/tk2100IIsup2.hkl
Contains datablock II

CCDC reference: 630492

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.106
  • Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.6497 Proportion of unique data used 0.5726 Ratio reflections to parameters 9.2670 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.27 PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 .. 5.03 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2003); cell refinement: CrystalStructure; data reduction: CRYSTALS (Betteridge et al., 2003); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: CRYSTALS; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CRYSTALS.

6-Nitro-1-(phenylsulfonyl)-1H-indole top
Crystal data top
C14H10N2O4SZ = 2
Mr = 302.30F(000) = 312
Triclinic, P1Dx = 1.487 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 7.8846 (10) ÅCell parameters from 24 reflections
b = 7.9971 (16) Åθ = 16.3–20.0°
c = 11.5181 (8) ŵ = 0.26 mm1
α = 81.20 (1)°T = 296 K
β = 91.080 (8)°Prism, yellow
γ = 109.782 (10)°0.60 × 0.40 × 0.40 mm
V = 674.93 (17) Å3
Data collection top
Rigaku AFC6S
diffractometer
1770 reflections with I > 3σ(I)
Radiation source: normal-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 27.5°, θmin = 2.7°
ω/2θ scansh = 109
Absorption correction: ψ scan
(North et al., 1968)
k = 010
Tmin = 0.861, Tmax = 0.904l = 1414
3313 measured reflections3 standard reflections every 150 reflections
3091 independent reflections intensity decay: 1.2%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(F2) + (0.05P)2 + 0.29P],
where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.106(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.22 e Å3
1770 reflectionsΔρmin = 0.23 e Å3
191 parametersExtinction correction: Larson (1970), equation 22
0 restraintsExtinction coefficient: 132 (15)
Primary atom site location: structure-invariant direct methods
Special details top

Experimental. IR (cm-1, KBr): 3105, 1592, 1527, 1507, 1450, 1428, 1370, 1342, 1268; 1H NMR (300 MHz, CDCl3): δ 8.91–8.92 (m, 1H), 8.13–8.17 (m, 1H), 7.94–7.97 (m, 2H), 7.86 (d, J = 3.6 Hz, 1H), 7.49–7.66 (m, 4H), 6.79 (d, J = 3.6 Hz, 1H); 13C NMR (75 MHz, CDCl3): δ 145.3, 137.8, 135.7, 134.7, 133.8, 131.4, 129.9, 127.1, 121.8, 118.9, 110.1, 109.0

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.14368 (10)0.20917 (10)0.16651 (6)0.0466
O10.0306 (3)0.1603 (3)0.07069 (19)0.0632
O20.1215 (3)0.3352 (3)0.23387 (19)0.0630
O30.3492 (6)0.3617 (5)0.6041 (3)0.1214
O40.3909 (6)0.1566 (6)0.7349 (3)0.1371
N10.1077 (3)0.0177 (3)0.2599 (2)0.0470
N20.3479 (5)0.2085 (6)0.6380 (3)0.0836
C20.0764 (4)0.1473 (4)0.2205 (3)0.0563
C40.1763 (4)0.1726 (4)0.4042 (3)0.0559
C30.1137 (5)0.2624 (4)0.3053 (3)0.0658
C50.2339 (5)0.2221 (5)0.5170 (4)0.0768
C60.2883 (5)0.0982 (6)0.5920 (3)0.0771
C70.2866 (4)0.0750 (5)0.5565 (3)0.0615
C90.1755 (4)0.0043 (4)0.3734 (2)0.0443
C80.2307 (4)0.1324 (4)0.4486 (2)0.0509
C100.3704 (4)0.2704 (3)0.1208 (2)0.0441
C110.5021 (5)0.3813 (4)0.1814 (3)0.0610
C120.6798 (6)0.4214 (5)0.1457 (4)0.0843
C130.7210 (5)0.3530 (6)0.0517 (4)0.0840
C140.5877 (5)0.2451 (5)0.0092 (4)0.0775
C150.4109 (5)0.2027 (4)0.0248 (3)0.0595
H210.03280.17550.14080.0668*
H310.09860.39030.30080.0764*
H510.23320.34830.54230.0890*
H610.32940.13280.67190.0911*
H810.22960.25820.42470.0601*
H1110.46780.43110.24980.0688*
H1210.77910.50220.19120.0912*
H1310.85180.38600.02720.0951*
H1410.62120.19590.07830.0957*
H1510.31010.12460.02010.0766*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0508 (4)0.0519 (4)0.0466 (4)0.0268 (3)0.0102 (3)0.0151 (3)
O10.0587 (13)0.0829 (16)0.0578 (13)0.0337 (12)0.0239 (10)0.0207 (11)
O20.0814 (16)0.0612 (13)0.0635 (14)0.0421 (12)0.0041 (11)0.0199 (11)
O30.167 (4)0.117 (3)0.077 (2)0.030 (3)0.025 (2)0.050 (2)
O40.158 (4)0.198 (4)0.0591 (19)0.058 (3)0.041 (2)0.040 (2)
N10.0508 (14)0.0478 (14)0.0455 (13)0.0179 (11)0.0055 (11)0.0144 (10)
N20.079 (2)0.124 (3)0.0420 (18)0.023 (2)0.0066 (15)0.023 (2)
C20.0555 (18)0.0458 (17)0.066 (2)0.0106 (14)0.0019 (15)0.0195 (15)
C40.0523 (18)0.0493 (17)0.063 (2)0.0169 (14)0.0081 (15)0.0004 (15)
C30.069 (2)0.0400 (16)0.087 (2)0.0150 (16)0.0043 (18)0.0138 (17)
C50.076 (2)0.071 (2)0.080 (3)0.033 (2)0.009 (2)0.019 (2)
C60.068 (2)0.107 (3)0.051 (2)0.032 (2)0.0030 (17)0.006 (2)
C70.0494 (18)0.087 (2)0.0443 (17)0.0169 (17)0.0002 (14)0.0131 (16)
C90.0380 (14)0.0515 (16)0.0426 (15)0.0140 (12)0.0016 (12)0.0071 (12)
C80.0469 (16)0.0617 (19)0.0435 (16)0.0161 (14)0.0017 (13)0.0116 (14)
C100.0499 (16)0.0390 (14)0.0461 (15)0.0208 (12)0.0087 (12)0.0021 (12)
C110.062 (2)0.0493 (17)0.062 (2)0.0078 (15)0.0125 (16)0.0048 (15)
C120.063 (2)0.067 (2)0.095 (3)0.0010 (19)0.023 (2)0.016 (2)
C130.053 (2)0.077 (3)0.112 (4)0.031 (2)0.012 (2)0.036 (3)
C140.072 (2)0.078 (2)0.091 (3)0.042 (2)0.017 (2)0.002 (2)
C150.063 (2)0.0611 (19)0.062 (2)0.0293 (16)0.0006 (16)0.0144 (16)
Geometric parameters (Å, º) top
S1—O11.423 (2)C6—C71.387 (5)
S1—O21.419 (2)C6—H611.000
S1—N11.672 (2)C7—C81.375 (4)
S1—C101.754 (3)C9—C81.395 (4)
O3—N21.225 (5)C8—H811.004
O4—N21.213 (4)C10—C111.376 (4)
N1—C21.402 (4)C10—C151.389 (4)
N1—C91.406 (3)C11—C121.383 (6)
N2—C71.482 (5)C11—H1111.015
C2—C31.335 (5)C12—C131.375 (6)
C2—H211.006C12—H1211.025
C4—C31.431 (5)C13—C141.373 (6)
C4—C51.412 (5)C13—H1311.008
C4—C91.407 (4)C14—C151.368 (5)
C3—H310.998C14—H1411.016
C5—C61.369 (5)C15—H1511.018
C5—H511.004
O1—S1—O2120.37 (14)N2—C7—C6119.2 (3)
O1—S1—N1105.33 (13)N2—C7—C8116.9 (3)
O2—S1—N1106.19 (12)C6—C7—C8123.9 (3)
O1—S1—C10109.72 (13)C4—C9—N1107.1 (2)
O2—S1—C10110.21 (14)C4—C9—C8123.0 (3)
N1—S1—C10103.51 (12)N1—C9—C8129.9 (3)
S1—N1—C2121.9 (2)C9—C8—C7115.6 (3)
S1—N1—C9125.28 (19)C9—C8—H81121.7
C2—N1—C9107.7 (2)C7—C8—H81122.7
O3—N2—O4124.6 (4)S1—C10—C11119.3 (2)
O3—N2—C7118.2 (3)S1—C10—C15118.5 (2)
O4—N2—C7117.2 (4)C11—C10—C15122.1 (3)
N1—C2—C3109.6 (3)C10—C11—C12117.8 (4)
N1—C2—H21125.6C10—C11—H111120.2
C3—C2—H21124.9C12—C11—H111122.0
C3—C4—C5135.0 (3)C11—C12—C13120.4 (4)
C3—C4—C9106.9 (3)C11—C12—H121118.4
C5—C4—C9118.1 (3)C13—C12—H121121.2
C4—C3—C2108.6 (3)C12—C13—C14121.1 (4)
C4—C3—H31125.7C12—C13—H131118.5
C2—C3—H31125.7C14—C13—H131120.5
C4—C5—C6119.7 (3)C13—C14—C15119.7 (4)
C4—C5—H51120.0C13—C14—H141119.8
C6—C5—H51120.3C15—C14—H141120.5
C5—C6—C7119.7 (3)C10—C15—C14118.9 (3)
C5—C6—H61119.8C10—C15—H151120.3
C7—C6—H61120.4C14—C15—H151120.8
 

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