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

The crystal structure of the title compound, C₁₄H₁₀N₂O₄S, confirms the position of the nitro group at position C-3 of the indole ring system. While the nitro group is coplanar with the indole ring system, the angle between the indole and phenyl planes is 83.9 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.087
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   N2      ..       5.33 su

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

   1 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
   1 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

---

Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-NT (Bruker, 2006); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

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

Crystal data

C14H10N2O4S	F(000) = 624
Mr = 302.31	Dx = 1.568 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8345 reflections
a = 14.8141 (2) Å	θ = 2.3–33.1°
b = 4.8664 (1) Å	µ = 0.27 mm^−1
c = 18.9508 (2) Å	T = 100 K
β = 110.403 (5)°	Prism, yellow
V = 1280.48 (5) Å^3	0.32 × 0.15 × 0.12 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer	3587 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 33.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −21→22
Tmin = 0.918, Tmax = 0.967	k = −7→7
20478 measured reflections	l = −29→29
4339 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(F^2) + (0.03P)^2 + 0.4P], where P = [max(Fo^2,0) + 2Fc^2]/3
S = 1.02	(Δ/σ)max = 0.007
3587 reflections	Δρmax = 0.38 e Å^−3
190 parameters	Δρmin = −0.37 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
S1	0.945324 (19)	−0.17615 (5)	0.117428 (15)	0.0123
O1	0.98255 (6)	−0.22785 (19)	0.05869 (5)	0.0171
O2	0.91519 (6)	−0.39331 (18)	0.15458 (5)	0.0175
N1	0.84467 (7)	0.0128 (2)	0.07664 (5)	0.0126
C2	0.83657 (8)	0.1976 (2)	0.01970 (6)	0.0130
H2	0.8810	0.2203	−0.0060	0.0500*
C3	0.75327 (8)	0.3413 (2)	0.00694 (6)	0.0136
N2	0.72301 (7)	0.5558 (2)	−0.04703 (6)	0.0168
O3	0.64857 (7)	0.6814 (2)	−0.05197 (5)	0.0239
O4	0.77271 (7)	0.6079 (2)	−0.08566 (5)	0.0239
C4	0.61945 (9)	0.3173 (3)	0.06747 (7)	0.0187
H4	0.5780	0.4552	0.0377	0.0500*
C5	0.59584 (9)	0.1774 (3)	0.12189 (8)	0.0214
H5	0.5366	0.2169	0.1289	0.0500*
C6	0.65738 (9)	−0.0218 (3)	0.16714 (7)	0.0208
H6	0.6396	−0.1111	0.2049	0.0500*
C7	0.74334 (9)	−0.0922 (3)	0.15795 (7)	0.0172
H7	0.7850	−0.2285	0.1885	0.0500*
C8	0.70612 (8)	0.2510 (2)	0.05721 (6)	0.0138
C9	0.76607 (8)	0.0462 (2)	0.10197 (6)	0.0131
C10	1.02278 (8)	0.0444 (2)	0.18392 (6)	0.0129
C11	1.09092 (8)	0.1930 (2)	0.16500 (7)	0.0161
H11	1.0969	0.1720	0.1169	0.0500*
C12	1.15008 (9)	0.3731 (3)	0.21788 (8)	0.0198
H12	1.1979	0.4753	0.2064	0.0500*
C13	1.13966 (9)	0.4043 (3)	0.28754 (7)	0.0207
H13	1.1802	0.5290	0.3233	0.0500*
C14	1.07055 (9)	0.2547 (3)	0.30523 (7)	0.0197
H14	1.0637	0.2779	0.3530	0.0500*
C15	1.01160 (9)	0.0714 (2)	0.25354 (7)	0.0165
H15	0.9645	−0.0334	0.2653	0.0500*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01121 (12)	0.01122 (12)	0.01397 (12)	0.00119 (9)	0.00360 (9)	−0.00094 (9)
O1	0.0150 (4)	0.0194 (4)	0.0180 (4)	0.0021 (3)	0.0070 (3)	−0.0045 (3)
O2	0.0176 (4)	0.0122 (4)	0.0217 (4)	0.0004 (3)	0.0055 (3)	0.0027 (3)
N1	0.0107 (4)	0.0142 (4)	0.0131 (4)	0.0017 (3)	0.0044 (3)	0.0012 (3)
C2	0.0127 (4)	0.0146 (5)	0.0112 (4)	−0.0006 (4)	0.0034 (4)	−0.0004 (4)
C3	0.0130 (4)	0.0148 (5)	0.0115 (4)	0.0006 (4)	0.0024 (4)	0.0001 (4)
N2	0.0163 (4)	0.0169 (5)	0.0129 (4)	0.0003 (3)	−0.0004 (4)	0.0006 (3)
O3	0.0229 (4)	0.0230 (5)	0.0218 (4)	0.0098 (4)	0.0029 (4)	0.0032 (4)
O4	0.0219 (4)	0.0286 (5)	0.0205 (4)	0.0001 (4)	0.0066 (4)	0.0092 (4)
C4	0.0127 (5)	0.0228 (6)	0.0196 (5)	0.0022 (4)	0.0044 (4)	−0.0039 (4)
C5	0.0144 (5)	0.0284 (6)	0.0238 (6)	−0.0009 (4)	0.0095 (5)	−0.0065 (5)
C6	0.0200 (6)	0.0254 (6)	0.0201 (5)	−0.0045 (5)	0.0109 (5)	−0.0030 (5)
C7	0.0173 (5)	0.0185 (5)	0.0164 (5)	−0.0021 (4)	0.0067 (4)	0.0003 (4)
C8	0.0118 (4)	0.0152 (5)	0.0132 (4)	0.0003 (4)	0.0028 (4)	−0.0024 (4)
C9	0.0110 (4)	0.0148 (5)	0.0135 (4)	−0.0008 (3)	0.0042 (4)	−0.0016 (4)
C10	0.0118 (4)	0.0124 (4)	0.0133 (4)	0.0017 (3)	0.0029 (4)	−0.0002 (4)
C11	0.0131 (5)	0.0173 (5)	0.0180 (5)	0.0002 (4)	0.0057 (4)	−0.0026 (4)
C12	0.0140 (5)	0.0195 (6)	0.0242 (6)	−0.0024 (4)	0.0047 (5)	−0.0052 (4)
C13	0.0171 (5)	0.0197 (5)	0.0205 (5)	0.0021 (4)	0.0004 (5)	−0.0059 (4)
C14	0.0215 (6)	0.0217 (6)	0.0131 (5)	0.0052 (4)	0.0023 (4)	−0.0014 (4)
C15	0.0174 (5)	0.0173 (5)	0.0142 (5)	0.0027 (4)	0.0047 (4)	0.0020 (4)

Geometric parameters (Å, º)

S1—O1	1.4264 (9)	C6—H6	0.950
S1—O2	1.4251 (9)	C6—C7	1.3869 (18)
S1—N1	1.6918 (10)	C7—H7	0.952
S1—C10	1.7458 (11)	C7—C9	1.3934 (16)
N1—C2	1.3774 (14)	C8—C9	1.4060 (16)
N1—C9	1.4152 (15)	C10—C11	1.3866 (17)
C2—H2	0.952	C10—C15	1.3922 (16)
C2—C3	1.3646 (16)	C11—H11	0.952
C3—N2	1.4203 (15)	C11—C12	1.3888 (16)
C3—C8	1.4326 (16)	C12—H12	0.951
N2—O3	1.2355 (14)	C12—C13	1.3897 (19)
N2—O4	1.2322 (14)	C13—H13	0.951
C4—H4	0.951	C13—C14	1.389 (2)
C4—C5	1.3788 (19)	C14—H14	0.952
C4—C8	1.4015 (17)	C14—C15	1.3861 (17)
C5—H5	0.952	C15—H15	0.952
C5—C6	1.4004 (19)
O1—S1—O2	121.84 (5)	C6—C7—H7	121.6
O1—S1—N1	104.97 (5)	C6—C7—C9	116.89 (11)
O2—S1—N1	104.52 (5)	H7—C7—C9	121.5
O1—S1—C10	109.63 (5)	C3—C8—C4	134.77 (11)
O2—S1—C10	109.85 (5)	C3—C8—C9	105.47 (10)
N1—S1—C10	104.39 (5)	C4—C8—C9	119.73 (11)
S1—N1—C2	122.34 (8)	N1—C9—C8	107.34 (10)
S1—N1—C9	127.28 (8)	N1—C9—C7	130.44 (11)
C2—N1—C9	109.48 (9)	C8—C9—C7	122.18 (11)
N1—C2—H2	126.1	S1—C10—C11	119.25 (9)
N1—C2—C3	107.45 (10)	S1—C10—C15	118.47 (9)
H2—C2—C3	126.4	C11—C10—C15	122.25 (11)
C2—C3—N2	122.90 (11)	C10—C11—H11	120.7
C2—C3—C8	110.21 (10)	C10—C11—C12	118.42 (11)
N2—C3—C8	126.84 (10)	H11—C11—C12	120.8
C3—N2—O3	117.88 (11)	C11—C12—H12	119.9
C3—N2—O4	118.37 (10)	C11—C12—C13	120.20 (12)
O3—N2—O4	123.75 (11)	H12—C12—C13	119.9
H4—C4—C5	120.8	C12—C13—H13	119.7
H4—C4—C8	120.9	C12—C13—C14	120.50 (11)
C5—C4—C8	118.28 (12)	H13—C13—C14	119.8
C4—C5—H5	119.4	C13—C14—H14	120.0
C4—C5—C6	121.27 (12)	C13—C14—C15	120.16 (11)
H5—C5—C6	119.3	H14—C14—C15	119.9
C5—C6—H6	119.1	C10—C15—C14	118.47 (11)
C5—C6—C7	121.62 (12)	C10—C15—H15	120.7
H6—C6—C7	119.3	C14—C15—H15	120.8