6-Nitro-1-(phenyl­sulfon­yl)-1H-indole

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)°.

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

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(F^2) + (0.05P)^2 + 0.29P], where P = [max(Fo^2,0) + 2Fc^2]/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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