2-Nitro-N-phenyl­benzene­sulfonamide

In the title compound, C₁₂H₁₀N₂O₄S, the conformation of the N—H bond in the –SO₂—NH– fragment is syn to the ortho-nitro group in the sulfonyl­benzene ring. The mol­ecule is twisted at the S—N bond, the C—N—S—C torsion angle being −72.83 (15)°. The dihedral angle between the benzene rings is 59.55 (7)°. The amide H atom and the nitro group O atom form an intra­molecular hydrogen bond, generating an S(7) motif. In the crystal, C—H⋯O hydrogen-bond inter­actions link the mol­ecules into S₂²(10) networks.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Alkan et al. (2011); Bowes et al. (2003); Gowda et al. (2000); Saeed et al. (2010); Shahwar et al. (2012), of N-aroylsulfonamides, see: Suchetan et al. (2012), of N-chloro­aryl­sulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004) and of N-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006).

Experimental

Crystal data

• C₁₂H₁₀N₂O₄S

• M_r = 278.28

• Monoclinic, P 2₁ /c

• a = 13.308 (2) Å

• b = 6.1629 (7) Å

• c = 15.285 (2) Å

• β = 100.80 (1)°

• V = 1231.4 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.28 mm⁻¹

• T = 293 K

• 0.48 × 0.42 × 0.42 mm

Data collection

• Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

• Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) T_min = 0.880, T_max = 0.893

• 4580 measured reflections

• 2516 independent reflections

• 1942 reflections with I > 2σ(I)

• R_int = 0.013

Refinement

• R[F² > 2σ(F²)] = 0.035

• wR(F²) = 0.096

• S = 1.04

• 2516 reflections

• 175 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.18 e Å⁻³

• Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.84 (1)	2.21 (2)	2.897 (2)	139 (2)
C3—H3⋯O4^i	0.93	2.56	3.451 (2)	162
Symmetry code: (i) -x, -y-1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supporting information

S1. Comment

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Bowes et al., 2003; Gowda et al., 2000; Saeed et al., 2010; Shahwar et al., 2012); N-aroylsulfonamides (Suchetan et al., 2012); N-chloroarylsulfonamides (Gowda et al., 2005; Shetty & Gowda, 2004) and N-bromoarylsulfonamides (Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of N-(phenyl)-2-nitrobenzenesulfonamide has been determined (Fig. 1).

The conformation of the N—H bond in the —SO₂—NH— segment is syn to the ortho-nitro group in the sulfonyl benzene ring, similar to that observed in N-(benzoyl)-2-nitrobenzenesulfonamide (I) (Suchetan et al., 2012). The molecule is twisted at the S—N bond with the torsional angle of -72.83 (15)°, compared to the value of -63.39 (22)° in (I).

The dihedral angle between the sulfonyl and the anilino rings is 59.55 (7)°, compared to the value of 88.6 (1)° in (I).

The amide H-atom showed intramolecular H-bonding with the O-atom of the ortho-nitro group in the sulfonyl benzene ring (Table 1).

In the crystal, the intermolecular C–H···O hydrogen bond interactions link the molecules. Part of the crystal structure is shown in Fig. 2.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011); Bowes et al. (2003); Gowda et al. (2000); Saeed et al. (2010); Shahwar et al. (2012), of N-aroylsulfonamides, see: Suchetan et al. (2012), of N-chloroarylsulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006).

S2. Experimental

The title compound was prepared by treating 2-nitrobenzenesulfonylchloride with aniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(phenyl)-2-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.

S3. Refinement

H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å. The amino H atom was freely refined with the N—H distances restrained to 0.86 (1) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 U_eq of the parent atom. The (-2 0 4) reflection was probably affected by the beamstop and was omitted from the refinement.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

2-Nitro-N-phenylbenzenesulfonamide

Crystal data

C12H10N2O4S	F(000) = 576
Mr = 278.28	Dx = 1.501 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1497 reflections
a = 13.308 (2) Å	θ = 3.1–27.8°
b = 6.1629 (7) Å	µ = 0.28 mm^−1
c = 15.285 (2) Å	T = 293 K
β = 100.80 (1)°	Prism, colourless
V = 1231.4 (3) Å^3	0.48 × 0.42 × 0.42 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2516 independent reflections
Radiation source: fine-focus sealed tube	1942 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −16→16
Tmin = 0.880, Tmax = 0.893	k = −4→7
4580 measured reflections	l = −18→19

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.178P] where P = (Fo^2 + 2Fc^2)/3
2516 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.18 e Å^−3
1 restraint	Δρmin = −0.34 e Å^−3

Special details

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.18707 (12)	0.0643 (3)	0.09270 (10)	0.0368 (4)
C2	0.13182 (12)	−0.1185 (3)	0.05925 (10)	0.0390 (4)
C3	0.08257 (14)	−0.2461 (3)	0.11177 (12)	0.0512 (4)
H3	0.0445	−0.3655	0.0876	0.061*
C4	0.09012 (15)	−0.1954 (4)	0.20065 (12)	0.0590 (5)
H4	0.0582	−0.2827	0.2369	0.071*
C5	0.14426 (14)	−0.0176 (4)	0.23550 (11)	0.0552 (5)
H5	0.1496	0.0152	0.2956	0.066*
C6	0.19116 (13)	0.1139 (3)	0.18203 (10)	0.0464 (4)
H6	0.2260	0.2373	0.2061	0.056*
C7	0.43841 (12)	0.1244 (3)	0.07735 (10)	0.0385 (4)
C8	0.46081 (14)	−0.0675 (3)	0.12345 (11)	0.0488 (4)
H8	0.4161	−0.1847	0.1130	0.059*
C9	0.55091 (16)	−0.0829 (3)	0.18565 (12)	0.0587 (5)
H9	0.5666	−0.2113	0.2172	0.070*
C10	0.61684 (15)	0.0889 (4)	0.20105 (12)	0.0588 (5)
H10	0.6774	0.0764	0.2424	0.071*
C11	0.59370 (15)	0.2795 (3)	0.15553 (13)	0.0561 (5)
H11	0.6387	0.3961	0.1659	0.067*
C12	0.50405 (14)	0.2984 (3)	0.09449 (11)	0.0476 (4)
H12	0.4877	0.4290	0.0647	0.057*
N1	0.34907 (11)	0.1444 (3)	0.00839 (9)	0.0478 (4)
H1N	0.3328 (15)	0.037 (2)	−0.0247 (11)	0.057*
N2	0.12429 (12)	−0.1899 (2)	−0.03419 (9)	0.0461 (4)
O1	0.17706 (11)	0.2775 (2)	−0.05490 (9)	0.0635 (4)
O2	0.27405 (10)	0.4356 (2)	0.08413 (8)	0.0586 (4)
O3	0.19974 (11)	−0.1782 (3)	−0.06778 (8)	0.0640 (4)
O4	0.04257 (10)	−0.2632 (2)	−0.07212 (9)	0.0648 (4)
S1	0.24456 (3)	0.25201 (7)	0.02828 (3)	0.04409 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0317 (7)	0.0421 (9)	0.0360 (8)	0.0075 (7)	0.0047 (6)	0.0002 (7)
C2	0.0361 (8)	0.0433 (9)	0.0374 (8)	0.0070 (7)	0.0063 (6)	−0.0010 (7)
C3	0.0449 (10)	0.0502 (11)	0.0588 (11)	−0.0034 (9)	0.0108 (8)	0.0016 (8)
C4	0.0532 (11)	0.0749 (14)	0.0526 (11)	−0.0003 (11)	0.0194 (9)	0.0137 (10)
C5	0.0497 (10)	0.0798 (14)	0.0374 (9)	0.0055 (11)	0.0113 (8)	0.0014 (9)
C6	0.0394 (9)	0.0585 (11)	0.0398 (9)	0.0041 (8)	0.0037 (7)	−0.0061 (8)
C7	0.0388 (8)	0.0465 (10)	0.0338 (8)	0.0017 (7)	0.0157 (6)	−0.0007 (7)
C8	0.0534 (10)	0.0418 (10)	0.0561 (10)	0.0010 (8)	0.0228 (9)	0.0019 (8)
C9	0.0625 (12)	0.0580 (13)	0.0591 (12)	0.0222 (11)	0.0203 (10)	0.0154 (9)
C10	0.0476 (10)	0.0743 (15)	0.0526 (11)	0.0154 (11)	0.0047 (9)	−0.0038 (10)
C11	0.0449 (10)	0.0609 (13)	0.0625 (12)	−0.0069 (9)	0.0098 (9)	−0.0093 (9)
C12	0.0529 (10)	0.0446 (10)	0.0478 (10)	−0.0006 (8)	0.0160 (8)	0.0060 (8)
N1	0.0439 (8)	0.0620 (10)	0.0384 (7)	−0.0007 (7)	0.0104 (6)	−0.0063 (7)
N2	0.0475 (9)	0.0450 (8)	0.0435 (8)	0.0038 (7)	0.0026 (7)	−0.0051 (6)
O1	0.0589 (8)	0.0723 (10)	0.0542 (8)	0.0027 (7)	−0.0028 (6)	0.0237 (7)
O2	0.0607 (8)	0.0415 (7)	0.0743 (9)	−0.0007 (6)	0.0141 (7)	−0.0046 (6)
O3	0.0619 (9)	0.0840 (10)	0.0503 (7)	−0.0101 (8)	0.0210 (7)	−0.0195 (7)
O4	0.0516 (8)	0.0744 (10)	0.0616 (8)	−0.0036 (7)	−0.0072 (7)	−0.0177 (7)
S1	0.0440 (3)	0.0435 (3)	0.0438 (2)	0.00341 (19)	0.00569 (18)	0.00595 (18)

Geometric parameters (Å, º)

C1—C2	1.390 (2)	C8—C9	1.387 (3)
C1—C6	1.390 (2)	C8—H8	0.9300
C1—S1	1.7819 (16)	C9—C10	1.367 (3)
C2—C3	1.375 (2)	C9—H9	0.9300
C2—N2	1.480 (2)	C10—C11	1.370 (3)
C3—C4	1.379 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.375 (3)
C4—C5	1.364 (3)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.380 (3)	N1—S1	1.6202 (16)
C5—H5	0.9300	N1—H1N	0.838 (9)
C6—H6	0.9300	N2—O3	1.2125 (18)
C7—C12	1.377 (2)	N2—O4	1.2193 (19)
C7—C8	1.380 (2)	O1—S1	1.4213 (13)
C7—N1	1.439 (2)	O2—S1	1.4276 (13)
C2—C1—C6	117.40 (15)	C10—C9—C8	120.63 (18)
C2—C1—S1	125.13 (12)	C10—C9—H9	119.7
C6—C1—S1	117.28 (13)	C8—C9—H9	119.7
C3—C2—C1	121.75 (15)	C9—C10—C11	120.03 (18)
C3—C2—N2	116.12 (15)	C9—C10—H10	120.0
C1—C2—N2	122.12 (14)	C11—C10—H10	120.0
C2—C3—C4	119.42 (18)	C10—C11—C12	120.08 (18)
C2—C3—H3	120.3	C10—C11—H11	120.0
C4—C3—H3	120.3	C12—C11—H11	120.0
C5—C4—C3	120.15 (18)	C11—C12—C7	120.13 (17)
C5—C4—H4	119.9	C11—C12—H12	119.9
C3—C4—H4	119.9	C7—C12—H12	119.9
C4—C5—C6	120.32 (16)	C7—N1—S1	121.21 (11)
C4—C5—H5	119.8	C7—N1—H1N	117.3 (14)
C6—C5—H5	119.8	S1—N1—H1N	107.7 (14)
C5—C6—C1	120.91 (17)	O3—N2—O4	123.79 (15)
C5—C6—H6	119.5	O3—N2—C2	118.65 (14)
C1—C6—H6	119.5	O4—N2—C2	117.52 (15)
C12—C7—C8	120.10 (16)	O1—S1—O2	120.27 (8)
C12—C7—N1	118.71 (15)	O1—S1—N1	107.35 (8)
C8—C7—N1	121.14 (16)	O2—S1—N1	106.69 (8)
C7—C8—C9	119.01 (18)	O1—S1—C1	107.54 (8)
C7—C8—H8	120.5	O2—S1—C1	106.41 (8)
C9—C8—H8	120.5	N1—S1—C1	108.10 (8)
C6—C1—C2—C3	0.2 (2)	C8—C7—C12—C11	2.1 (3)
S1—C1—C2—C3	−174.56 (13)	N1—C7—C12—C11	−175.41 (16)
C6—C1—C2—N2	−178.48 (14)	C12—C7—N1—S1	−84.88 (18)
S1—C1—C2—N2	6.8 (2)	C8—C7—N1—S1	97.67 (17)
C1—C2—C3—C4	−1.7 (3)	C3—C2—N2—O3	−138.87 (18)
N2—C2—C3—C4	177.03 (16)	C1—C2—N2—O3	39.9 (2)
C2—C3—C4—C5	1.4 (3)	C3—C2—N2—O4	39.1 (2)
C3—C4—C5—C6	0.5 (3)	C1—C2—N2—O4	−142.16 (17)
C4—C5—C6—C1	−2.1 (3)	C7—N1—S1—O1	171.43 (14)
C2—C1—C6—C5	1.7 (2)	C7—N1—S1—O2	41.27 (16)
S1—C1—C6—C5	176.89 (13)	C7—N1—S1—C1	−72.83 (15)
C12—C7—C8—C9	−1.2 (2)	C2—C1—S1—O1	37.94 (16)
N1—C7—C8—C9	176.21 (15)	C6—C1—S1—O1	−136.83 (14)
C7—C8—C9—C10	−0.2 (3)	C2—C1—S1—O2	168.05 (14)
C8—C9—C10—C11	0.7 (3)	C6—C1—S1—O2	−6.72 (15)
C9—C10—C11—C12	0.2 (3)	C2—C1—S1—N1	−77.68 (15)
C10—C11—C12—C7	−1.5 (3)	C6—C1—S1—N1	107.56 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.84 (1)	2.21 (2)	2.897 (2)	139 (2)
C3—H3···O4^i	0.93	2.56	3.451 (2)	162

Symmetry code: (i) −x, −y−1, −z.