4-Methyl-N-(3-nitro­phen­yl)benzene­sulfonamide

In the mol­ecule of the title compound, m-(O₂N)C₆H₄NHSO₂C₆H₄-p-Me or C₁₃H₁₂N₂O₄S, the planes of two benzene rings are orthogonal to each other [dihedral angle 92.4 (1)°].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.147
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Experimental

The title compound was prepared according to the method of Sprague & Miller (1952). To a solution of 3-nitroaniline (27.6 g) in pyridine (100 ml) was added 4-tosyl chloride (41.8 g); the mixture was heated for 0.5 h at 373 K, then cooled to room temperature and poured into 500 ml of dilute HCl, thus yielding 4-methyl-N-(3-nitrophenyl)-benzenesulfonamide in quantitative yield. The X-ray quality crystals of the title compound (m.p. 405–407 K) were obtained by slow evaporation of its ethanol solution.

S2. Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H 0.93 and 0.96 Å, and U_iso(H) = 1.2U_eq(C_aromatic,N) and 1.5U_eq(C_Me).

Computing details

Data collection: RAPID-AUTO (Rigaku, 1997); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: please supply; software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level; H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing of the crystal of the title compound, projected on to the ac plane; the N—H···O bonds are shown as dashed lines. H atoms attached to C atoms have been omitted.

4-Methyl-N-(3-nitrophenyl)benzenesulfonamide

Crystal data

C13H12N2O4S	F(000) = 608
Mr = 292.31	Dx = 1.482 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 10604 reflections
a = 12.766 (3) Å	θ = 3.0–27.5°
b = 7.7327 (15) Å	µ = 0.26 mm^−1
c = 13.550 (3) Å	T = 293 K
β = 101.66 (3)°	Block, light yellow
V = 1310.0 (5) Å^3	0.29 × 0.15 × 0.07 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2997 independent reflections
Radiation source: rotating anode	2519 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
oscillation scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→16
Tmin = 0.928, Tmax = 0.981	k = −10→9
12545 measured reflections	l = −17→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1119P)^2 + 0.1885P] where P = (Fo^2 + 2Fc^2)/3
2997 reflections	(Δ/σ)max = 0.005
181 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
S1	0.46196 (3)	0.09564 (5)	0.71566 (3)	0.03250 (17)
N1	0.62332 (12)	0.2537 (2)	1.10913 (11)	0.0371 (4)
N2	0.37809 (11)	0.1468 (2)	0.78721 (11)	0.0362 (3)
H2A	0.3114	0.1298	0.7622	0.043*
O1	0.69094 (11)	0.1694 (2)	1.07943 (12)	0.0545 (4)
O2	0.64034 (13)	0.3258 (2)	1.19147 (11)	0.0551 (4)
O3	0.39586 (12)	0.02293 (18)	0.62717 (10)	0.0447 (4)
O4	0.54622 (11)	−0.00586 (18)	0.77295 (11)	0.0426 (3)
C1	0.32062 (14)	0.2970 (2)	0.92168 (15)	0.0376 (4)
H1A	0.2535	0.3070	0.8799	0.045*
C2	0.33747 (16)	0.3626 (3)	1.01826 (16)	0.0436 (4)
H2B	0.2815	0.4164	1.0407	0.052*
C3	0.43667 (15)	0.3495 (3)	1.08235 (14)	0.0383 (4)
H3A	0.4487	0.3923	1.1478	0.046*
C4	0.51683 (13)	0.2697 (2)	1.04410 (13)	0.0309 (4)
C5	0.50296 (13)	0.2018 (2)	0.94798 (13)	0.0312 (4)
H5A	0.5592	0.1483	0.9256	0.037*
C6	0.40289 (13)	0.2159 (2)	0.88594 (12)	0.0302 (3)
C7	0.51791 (13)	0.2911 (2)	0.68361 (12)	0.0303 (3)
C8	0.62626 (15)	0.2973 (3)	0.68341 (17)	0.0440 (5)
H8A	0.6694	0.2013	0.7026	0.053*
C9	0.66956 (16)	0.4490 (3)	0.65409 (18)	0.0476 (5)
H9A	0.7422	0.4537	0.6535	0.057*
C10	0.60665 (17)	0.5932 (2)	0.62576 (14)	0.0378 (4)
C11	0.49822 (16)	0.5831 (2)	0.62596 (15)	0.0393 (4)
H11A	0.4549	0.6788	0.6066	0.047*
C12	0.45353 (15)	0.4328 (2)	0.65451 (14)	0.0362 (4)
H12A	0.3807	0.4275	0.6541	0.043*
C13	0.6542 (2)	0.7581 (3)	0.59509 (17)	0.0517 (5)
H13A	0.5989	0.8433	0.5772	0.077*
H13B	0.6865	0.7360	0.5382	0.077*
H13C	0.7075	0.8002	0.6503	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0320 (3)	0.0331 (3)	0.0306 (3)	−0.00429 (14)	0.00219 (18)	−0.00011 (14)
N1	0.0305 (8)	0.0457 (9)	0.0323 (8)	−0.0044 (6)	−0.0005 (6)	0.0065 (6)
N2	0.0232 (7)	0.0518 (9)	0.0315 (7)	−0.0046 (6)	0.0002 (5)	0.0014 (6)
O1	0.0289 (7)	0.0811 (11)	0.0494 (9)	0.0104 (7)	−0.0017 (6)	−0.0003 (8)
O2	0.0443 (8)	0.0788 (11)	0.0359 (8)	−0.0020 (8)	−0.0071 (6)	−0.0086 (7)
O3	0.0502 (8)	0.0446 (7)	0.0360 (7)	−0.0143 (6)	0.0009 (6)	−0.0056 (6)
O4	0.0407 (7)	0.0405 (7)	0.0451 (8)	0.0066 (5)	0.0054 (6)	0.0052 (5)
C1	0.0248 (8)	0.0424 (9)	0.0434 (10)	0.0036 (6)	0.0014 (7)	0.0056 (7)
C2	0.0338 (9)	0.0500 (11)	0.0476 (11)	0.0091 (8)	0.0097 (8)	0.0004 (8)
C3	0.0380 (9)	0.0419 (9)	0.0345 (9)	0.0009 (7)	0.0064 (7)	0.0010 (7)
C4	0.0257 (8)	0.0336 (8)	0.0312 (8)	−0.0029 (6)	0.0005 (6)	0.0068 (6)
C5	0.0242 (8)	0.0363 (8)	0.0323 (8)	0.0000 (6)	0.0040 (6)	0.0035 (6)
C6	0.0269 (8)	0.0321 (8)	0.0301 (8)	−0.0023 (6)	0.0026 (6)	0.0063 (6)
C7	0.0283 (8)	0.0336 (8)	0.0279 (7)	−0.0049 (6)	0.0031 (6)	−0.0025 (6)
C8	0.0288 (9)	0.0430 (10)	0.0591 (12)	0.0017 (7)	0.0066 (8)	0.0057 (8)
C9	0.0315 (10)	0.0522 (11)	0.0602 (13)	−0.0073 (8)	0.0118 (9)	0.0009 (10)
C10	0.0438 (10)	0.0411 (10)	0.0292 (8)	−0.0106 (7)	0.0090 (7)	−0.0033 (6)
C11	0.0396 (10)	0.0358 (9)	0.0414 (10)	0.0009 (7)	0.0052 (8)	−0.0004 (7)
C12	0.0285 (8)	0.0379 (9)	0.0421 (10)	−0.0008 (6)	0.0067 (7)	−0.0018 (7)
C13	0.0626 (14)	0.0488 (12)	0.0465 (11)	−0.0170 (10)	0.0181 (10)	−0.0004 (9)

Geometric parameters (Å, º)

S1—O4	1.4277 (14)	C5—C6	1.384 (2)
S1—O3	1.4341 (14)	C5—H5A	0.9300
S1—N2	1.6316 (16)	C7—C12	1.379 (2)
S1—C7	1.7628 (17)	C7—C8	1.385 (2)
N1—O1	1.213 (2)	C8—C9	1.389 (3)
N1—O2	1.227 (2)	C8—H8A	0.9300
N1—C4	1.468 (2)	C9—C10	1.382 (3)
N2—C6	1.416 (2)	C9—H9A	0.9300
N2—H2A	0.8600	C10—C11	1.387 (3)
C1—C2	1.379 (3)	C10—C13	1.506 (3)
C1—C6	1.392 (2)	C11—C12	1.383 (3)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.387 (3)	C12—H12A	0.9300
C2—H2B	0.9300	C13—H13A	0.9600
C3—C4	1.382 (3)	C13—H13B	0.9600
C3—H3A	0.9300	C13—H13C	0.9600
C4—C5	1.382 (2)
O4—S1—O3	119.37 (9)	C5—C6—C1	119.52 (16)
O4—S1—N2	108.83 (8)	C5—C6—N2	123.16 (16)
O3—S1—N2	104.23 (9)	C1—C6—N2	117.29 (16)
O4—S1—C7	107.87 (9)	C12—C7—C8	120.64 (16)
O3—S1—C7	109.24 (8)	C12—C7—S1	120.27 (13)
N2—S1—C7	106.61 (8)	C8—C7—S1	119.01 (14)
O1—N1—O2	122.59 (16)	C7—C8—C9	119.05 (18)
O1—N1—C4	118.73 (15)	C7—C8—H8A	120.5
O2—N1—C4	118.68 (16)	C9—C8—H8A	120.5
C6—N2—S1	127.20 (12)	C10—C9—C8	121.22 (18)
C6—N2—H2A	116.4	C10—C9—H9A	119.4
S1—N2—H2A	116.4	C8—C9—H9A	119.4
C2—C1—C6	120.80 (17)	C9—C10—C11	118.55 (17)
C2—C1—H1A	119.6	C9—C10—C13	121.04 (19)
C6—C1—H1A	119.6	C11—C10—C13	120.41 (19)
C1—C2—C3	120.98 (17)	C12—C11—C10	121.07 (17)
C1—C2—H2B	119.5	C12—C11—H11A	119.5
C3—C2—H2B	119.5	C10—C11—H11A	119.5
C4—C3—C2	116.70 (17)	C7—C12—C11	119.46 (17)
C4—C3—H3A	121.6	C7—C12—H12A	120.3
C2—C3—H3A	121.6	C11—C12—H12A	120.3
C3—C4—C5	124.01 (16)	C10—C13—H13A	109.5
C3—C4—N1	118.58 (16)	C10—C13—H13B	109.5
C5—C4—N1	117.41 (15)	H13A—C13—H13B	109.5
C4—C5—C6	117.99 (16)	C10—C13—H13C	109.5
C4—C5—H5A	121.0	H13A—C13—H13C	109.5
C6—C5—H5A	121.0	H13B—C13—H13C	109.5
O4—S1—N2—C6	48.29 (18)	S1—N2—C6—C1	161.38 (14)
O3—S1—N2—C6	176.69 (15)	O4—S1—C7—C12	−161.13 (14)
C7—S1—N2—C6	−67.82 (17)	O3—S1—C7—C12	67.70 (17)
C6—C1—C2—C3	0.0 (3)	N2—S1—C7—C12	−44.38 (16)
C1—C2—C3—C4	0.7 (3)	O4—S1—C7—C8	21.97 (17)
C2—C3—C4—C5	−0.9 (3)	O3—S1—C7—C8	−109.20 (16)
C2—C3—C4—N1	179.71 (17)	N2—S1—C7—C8	138.72 (15)
O1—N1—C4—C3	172.99 (17)	C12—C7—C8—C9	0.4 (3)
O2—N1—C4—C3	−6.8 (2)	S1—C7—C8—C9	177.31 (17)
O1—N1—C4—C5	−6.4 (2)	C7—C8—C9—C10	0.3 (3)
O2—N1—C4—C5	173.78 (16)	C8—C9—C10—C11	−0.8 (3)
C3—C4—C5—C6	0.6 (3)	C8—C9—C10—C13	179.3 (2)
N1—C4—C5—C6	179.92 (14)	C9—C10—C11—C12	0.5 (3)
C4—C5—C6—C1	0.1 (2)	C13—C10—C11—C12	−179.61 (18)
C4—C5—C6—N2	−178.00 (15)	C8—C7—C12—C11	−0.7 (3)
C2—C1—C6—C5	−0.4 (3)	S1—C7—C12—C11	−177.56 (14)
C2—C1—C6—N2	177.87 (17)	C10—C11—C12—C7	0.2 (3)
S1—N2—C6—C5	−20.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^i	0.86	2.23	3.058 (2)	162

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.