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organic compounds
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
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048616/tk2100sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048616/tk2100IIsup2.hkl |
CCDC reference: 630492
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.005 Å - R factor = 0.042
- wR factor = 0.106
- Data-to-parameter ratio = 9.3
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.005 ÅcheckCIF/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
Alert level C
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
| C14H10N2O4S | Z = 2 |
| Mr = 302.30 | F(000) = 312 |
| Triclinic, P1 | Dx = 1.487 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
| a = 7.8846 (10) Å | Cell parameters from 24 reflections |
| b = 7.9971 (16) Å | θ = 16.3–20.0° |
| c = 11.5181 (8) Å | µ = 0.26 mm−1 |
| 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 tube | Rint = 0.013 |
| Graphite monochromator | θmax = 27.5°, θmin = 2.7° |
| ω/2θ scans | h = −10→9 |
| Absorption correction: ψ scan (North et al., 1968) | k = 0→10 |
| Tmin = 0.861, Tmax = 0.904 | l = −14→14 |
| 3313 measured reflections | 3 standard reflections every 150 reflections |
| 3091 independent reflections | intensity decay: −1.2% |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-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 = 1.07 | Δρmax = 0.22 e Å−3 |
| 1770 reflections | Δρmin = −0.23 e Å−3 |
| 191 parameters | Extinction correction: Larson (1970), equation 22 |
| 0 restraints | Extinction 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
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.14368 (10) | 0.20917 (10) | 0.16651 (6) | 0.0466 | |
| O1 | 0.0306 (3) | 0.1603 (3) | 0.07069 (19) | 0.0632 | |
| O2 | 0.1215 (3) | 0.3352 (3) | 0.23387 (19) | 0.0630 | |
| O3 | 0.3492 (6) | 0.3617 (5) | 0.6041 (3) | 0.1214 | |
| O4 | 0.3909 (6) | 0.1566 (6) | 0.7349 (3) | 0.1371 | |
| N1 | 0.1077 (3) | 0.0177 (3) | 0.2599 (2) | 0.0470 | |
| N2 | 0.3479 (5) | 0.2085 (6) | 0.6380 (3) | 0.0836 | |
| C2 | 0.0764 (4) | −0.1473 (4) | 0.2205 (3) | 0.0563 | |
| C4 | 0.1763 (4) | −0.1726 (4) | 0.4042 (3) | 0.0559 | |
| C3 | 0.1137 (5) | −0.2624 (4) | 0.3053 (3) | 0.0658 | |
| C5 | 0.2339 (5) | −0.2221 (5) | 0.5170 (4) | 0.0768 | |
| C6 | 0.2883 (5) | −0.0982 (6) | 0.5920 (3) | 0.0771 | |
| C7 | 0.2866 (4) | 0.0750 (5) | 0.5565 (3) | 0.0615 | |
| C9 | 0.1755 (4) | 0.0043 (4) | 0.3734 (2) | 0.0443 | |
| C8 | 0.2307 (4) | 0.1324 (4) | 0.4486 (2) | 0.0509 | |
| C10 | 0.3704 (4) | 0.2704 (3) | 0.1208 (2) | 0.0441 | |
| C11 | 0.5021 (5) | 0.3813 (4) | 0.1814 (3) | 0.0610 | |
| C12 | 0.6798 (6) | 0.4214 (5) | 0.1457 (4) | 0.0843 | |
| C13 | 0.7210 (5) | 0.3530 (6) | 0.0517 (4) | 0.0840 | |
| C14 | 0.5877 (5) | 0.2451 (5) | −0.0092 (4) | 0.0775 | |
| C15 | 0.4109 (5) | 0.2027 (4) | 0.0248 (3) | 0.0595 | |
| H21 | 0.0328 | −0.1755 | 0.1408 | 0.0668* | |
| H31 | 0.0986 | −0.3903 | 0.3008 | 0.0764* | |
| H51 | 0.2332 | −0.3483 | 0.5423 | 0.0890* | |
| H61 | 0.3294 | −0.1328 | 0.6719 | 0.0911* | |
| H81 | 0.2296 | 0.2582 | 0.4247 | 0.0601* | |
| H111 | 0.4678 | 0.4311 | 0.2498 | 0.0688* | |
| H121 | 0.7791 | 0.5022 | 0.1912 | 0.0912* | |
| H131 | 0.8518 | 0.3860 | 0.0272 | 0.0951* | |
| H141 | 0.6212 | 0.1959 | −0.0783 | 0.0957* | |
| H151 | 0.3101 | 0.1246 | −0.0201 | 0.0766* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0508 (4) | 0.0519 (4) | 0.0466 (4) | 0.0268 (3) | −0.0102 (3) | −0.0151 (3) |
| O1 | 0.0587 (13) | 0.0829 (16) | 0.0578 (13) | 0.0337 (12) | −0.0239 (10) | −0.0207 (11) |
| O2 | 0.0814 (16) | 0.0612 (13) | 0.0635 (14) | 0.0421 (12) | −0.0041 (11) | −0.0199 (11) |
| O3 | 0.167 (4) | 0.117 (3) | 0.077 (2) | 0.030 (3) | −0.025 (2) | −0.050 (2) |
| O4 | 0.158 (4) | 0.198 (4) | 0.0591 (19) | 0.058 (3) | −0.041 (2) | −0.040 (2) |
| N1 | 0.0508 (14) | 0.0478 (14) | 0.0455 (13) | 0.0179 (11) | −0.0055 (11) | −0.0144 (10) |
| N2 | 0.079 (2) | 0.124 (3) | 0.0420 (18) | 0.023 (2) | −0.0066 (15) | −0.023 (2) |
| C2 | 0.0555 (18) | 0.0458 (17) | 0.066 (2) | 0.0106 (14) | −0.0019 (15) | −0.0195 (15) |
| C4 | 0.0523 (18) | 0.0493 (17) | 0.063 (2) | 0.0169 (14) | 0.0081 (15) | 0.0004 (15) |
| C3 | 0.069 (2) | 0.0400 (16) | 0.087 (2) | 0.0150 (16) | 0.0043 (18) | −0.0138 (17) |
| C5 | 0.076 (2) | 0.071 (2) | 0.080 (3) | 0.033 (2) | 0.009 (2) | 0.019 (2) |
| C6 | 0.068 (2) | 0.107 (3) | 0.051 (2) | 0.032 (2) | −0.0030 (17) | 0.006 (2) |
| C7 | 0.0494 (18) | 0.087 (2) | 0.0443 (17) | 0.0169 (17) | −0.0002 (14) | −0.0131 (16) |
| C9 | 0.0380 (14) | 0.0515 (16) | 0.0426 (15) | 0.0140 (12) | 0.0016 (12) | −0.0071 (12) |
| C8 | 0.0469 (16) | 0.0617 (19) | 0.0435 (16) | 0.0161 (14) | 0.0017 (13) | −0.0116 (14) |
| C10 | 0.0499 (16) | 0.0390 (14) | 0.0461 (15) | 0.0208 (12) | −0.0087 (12) | −0.0021 (12) |
| C11 | 0.062 (2) | 0.0493 (17) | 0.062 (2) | 0.0078 (15) | −0.0125 (16) | −0.0048 (15) |
| C12 | 0.063 (2) | 0.067 (2) | 0.095 (3) | −0.0010 (19) | −0.023 (2) | 0.016 (2) |
| C13 | 0.053 (2) | 0.077 (3) | 0.112 (4) | 0.031 (2) | 0.012 (2) | 0.036 (3) |
| C14 | 0.072 (2) | 0.078 (2) | 0.091 (3) | 0.042 (2) | 0.017 (2) | 0.002 (2) |
| C15 | 0.063 (2) | 0.0611 (19) | 0.062 (2) | 0.0293 (16) | −0.0006 (16) | −0.0144 (16) |
Geometric parameters (Å, º) top
| S1—O1 | 1.423 (2) | C6—C7 | 1.387 (5) |
| S1—O2 | 1.419 (2) | C6—H61 | 1.000 |
| S1—N1 | 1.672 (2) | C7—C8 | 1.375 (4) |
| S1—C10 | 1.754 (3) | C9—C8 | 1.395 (4) |
| O3—N2 | 1.225 (5) | C8—H81 | 1.004 |
| O4—N2 | 1.213 (4) | C10—C11 | 1.376 (4) |
| N1—C2 | 1.402 (4) | C10—C15 | 1.389 (4) |
| N1—C9 | 1.406 (3) | C11—C12 | 1.383 (6) |
| N2—C7 | 1.482 (5) | C11—H111 | 1.015 |
| C2—C3 | 1.335 (5) | C12—C13 | 1.375 (6) |
| C2—H21 | 1.006 | C12—H121 | 1.025 |
| C4—C3 | 1.431 (5) | C13—C14 | 1.373 (6) |
| C4—C5 | 1.412 (5) | C13—H131 | 1.008 |
| C4—C9 | 1.407 (4) | C14—C15 | 1.368 (5) |
| C3—H31 | 0.998 | C14—H141 | 1.016 |
| C5—C6 | 1.369 (5) | C15—H151 | 1.018 |
| C5—H51 | 1.004 | ||
| O1—S1—O2 | 120.37 (14) | N2—C7—C6 | 119.2 (3) |
| O1—S1—N1 | 105.33 (13) | N2—C7—C8 | 116.9 (3) |
| O2—S1—N1 | 106.19 (12) | C6—C7—C8 | 123.9 (3) |
| O1—S1—C10 | 109.72 (13) | C4—C9—N1 | 107.1 (2) |
| O2—S1—C10 | 110.21 (14) | C4—C9—C8 | 123.0 (3) |
| N1—S1—C10 | 103.51 (12) | N1—C9—C8 | 129.9 (3) |
| S1—N1—C2 | 121.9 (2) | C9—C8—C7 | 115.6 (3) |
| S1—N1—C9 | 125.28 (19) | C9—C8—H81 | 121.7 |
| C2—N1—C9 | 107.7 (2) | C7—C8—H81 | 122.7 |
| O3—N2—O4 | 124.6 (4) | S1—C10—C11 | 119.3 (2) |
| O3—N2—C7 | 118.2 (3) | S1—C10—C15 | 118.5 (2) |
| O4—N2—C7 | 117.2 (4) | C11—C10—C15 | 122.1 (3) |
| N1—C2—C3 | 109.6 (3) | C10—C11—C12 | 117.8 (4) |
| N1—C2—H21 | 125.6 | C10—C11—H111 | 120.2 |
| C3—C2—H21 | 124.9 | C12—C11—H111 | 122.0 |
| C3—C4—C5 | 135.0 (3) | C11—C12—C13 | 120.4 (4) |
| C3—C4—C9 | 106.9 (3) | C11—C12—H121 | 118.4 |
| C5—C4—C9 | 118.1 (3) | C13—C12—H121 | 121.2 |
| C4—C3—C2 | 108.6 (3) | C12—C13—C14 | 121.1 (4) |
| C4—C3—H31 | 125.7 | C12—C13—H131 | 118.5 |
| C2—C3—H31 | 125.7 | C14—C13—H131 | 120.5 |
| C4—C5—C6 | 119.7 (3) | C13—C14—C15 | 119.7 (4) |
| C4—C5—H51 | 120.0 | C13—C14—H141 | 119.8 |
| C6—C5—H51 | 120.3 | C15—C14—H141 | 120.5 |
| C5—C6—C7 | 119.7 (3) | C10—C15—C14 | 118.9 (3) |
| C5—C6—H61 | 119.8 | C10—C15—H151 | 120.3 |
| C7—C6—H61 | 120.4 | C14—C15—H151 | 120.8 |
