N-(2,5-Dimethyl-phen-yl)-2-nitro-benzene-sulfonamide.

In the crystal structure of the title compound, C14H14N2O4S, the N-H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and anti to the ortho- and syn to the meta-methyl groups in the aniline ring. The mol-ecule is twisted at the S-N bond with a torsion angle of 71.41 (18)°. The dihedral angle between the planes of the benzene rings is 51.07 (8)°. In the crystal, pairs of N-H⋯Osulfonamide hydrogen bonds link the mol-ecules into inversion dimers.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-aryl­sulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2002 ▶) and of N-chloro­aryl­sulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C14H14N2O4S

M = 306.33

Triclinic,

a = 8.1987 (7) Å

b = 9.6729 (9) Å

c = 9.9328 (9) Å

α = 84.386 (9)°

β = 72.096 (8)°

γ = 89.239 (9)°

V = 745.86 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.36 × 0.24 × 0.16 mm

Data collection

Oxford Diffraction Xcaliburdiffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.921, T max = 0.964

4954 measured reflections

3027 independent reflections

2629 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.14

3027 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.29 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047630/rz5026sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047630/rz5026Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047630/rz5026Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H14N2O4S	Z = 2
Mr = 306.33	F(000) = 320
Triclinic, P1	Dx = 1.364 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1987 (7) Å	Cell parameters from 3120 reflections
b = 9.6729 (9) Å	θ = 2.6–27.8°
c = 9.9328 (9) Å	µ = 0.23 mm−1
α = 84.386 (9)°	T = 293 K
β = 72.096 (8)°	Prism, light brown
γ = 89.239 (9)°	0.36 × 0.24 × 0.16 mm
V = 745.86 (12) Å3

Oxford Diffraction Xcaliburdiffractometer with Sapphire CCD	3027 independent reflections
Radiation source: fine-focus sealed tube	2629 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→10
Tmin = 0.921, Tmax = 0.964	k = −12→11
4954 measured reflections	l = −12→10

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.3685P] where P = (Fo2 + 2Fc2)/3
3027 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.3540 (2)	0.0929 (2)	0.6857 (2)	0.0387 (4)
C2	0.4684 (2)	0.0253 (2)	0.7467 (2)	0.0433 (4)
C3	0.6437 (3)	0.0467 (3)	0.6890 (3)	0.0561 (6)
H3	0.7187	−0.0016	0.7294	0.067*
C4	0.7051 (3)	0.1400 (3)	0.5713 (3)	0.0657 (7)
H4	0.8226	0.1564	0.5326	0.079*
C5	0.5947 (3)	0.2092 (3)	0.5104 (3)	0.0657 (7)
H5	0.6376	0.2732	0.4313	0.079*
C6	0.4199 (3)	0.1846 (2)	0.5655 (2)	0.0525 (5)
H6	0.3462	0.2299	0.5216	0.063*
C7	0.0552 (3)	0.3225 (2)	0.8314 (2)	0.0448 (5)
C8	0.1732 (3)	0.4106 (2)	0.8577 (2)	0.0567 (6)
C9	0.1583 (4)	0.5520 (3)	0.8214 (3)	0.0760 (8)
H9	0.2318	0.6147	0.8398	0.091*
C10	0.0386 (4)	0.6010 (3)	0.7595 (3)	0.0772 (9)
H10	0.0348	0.6961	0.7352	0.093*
C11	−0.0768 (4)	0.5141 (3)	0.7317 (3)	0.0701 (7)
C12	−0.0680 (3)	0.3728 (2)	0.7717 (2)	0.0546 (5)
H12	−0.1464	0.3114	0.7580	0.065*
C13	0.3075 (4)	0.3582 (3)	0.9231 (3)	0.0808 (9)
H13A	0.3794	0.2942	0.8642	0.121*
H13B	0.2531	0.3118	1.0159	0.121*
H13C	0.3759	0.4350	0.9310	0.121*
C14	−0.2091 (5)	0.5675 (4)	0.6626 (4)	0.1074 (12)
H14A	−0.1524	0.6151	0.5709	0.161*
H14B	−0.2833	0.6304	0.7213	0.161*
H14C	−0.2756	0.4907	0.6518	0.161*
N1	0.0568 (2)	0.17583 (17)	0.86856 (18)	0.0440 (4)
H1N	0.054 (3)	0.147 (2)	0.9500 (18)	0.053*
N2	0.4089 (3)	−0.0701 (2)	0.8773 (2)	0.0605 (5)
O1	0.06849 (18)	0.11008 (16)	0.63232 (16)	0.0524 (4)
O2	0.09053 (18)	−0.06778 (14)	0.82168 (17)	0.0530 (4)
O3	0.3174 (2)	−0.0226 (2)	0.98338 (19)	0.0766 (6)
O4	0.4595 (3)	−0.1884 (2)	0.8720 (3)	0.1039 (8)
S1	0.12780 (6)	0.06923 (5)	0.75061 (5)	0.04028 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0295 (9)	0.0461 (10)	0.0427 (10)	0.0008 (7)	−0.0130 (8)	−0.0090 (8)
C2	0.0392 (10)	0.0489 (11)	0.0462 (11)	0.0018 (8)	−0.0184 (8)	−0.0087 (9)
C3	0.0352 (10)	0.0803 (16)	0.0610 (14)	0.0081 (10)	−0.0235 (10)	−0.0184 (12)
C4	0.0340 (11)	0.107 (2)	0.0540 (13)	−0.0084 (12)	−0.0080 (10)	−0.0155 (13)
C5	0.0470 (12)	0.0948 (19)	0.0483 (13)	−0.0161 (12)	−0.0074 (10)	0.0054 (12)
C6	0.0427 (11)	0.0664 (14)	0.0482 (12)	−0.0028 (10)	−0.0159 (9)	0.0026 (10)
C7	0.0419 (10)	0.0408 (10)	0.0425 (10)	−0.0039 (8)	0.0003 (8)	−0.0034 (8)
C8	0.0508 (12)	0.0569 (13)	0.0516 (12)	−0.0120 (10)	0.0032 (10)	−0.0149 (10)
C9	0.0778 (18)	0.0586 (16)	0.0737 (18)	−0.0236 (14)	0.0073 (15)	−0.0178 (13)
C10	0.099 (2)	0.0401 (13)	0.0682 (17)	−0.0027 (14)	0.0094 (16)	−0.0016 (12)
C11	0.0859 (19)	0.0550 (15)	0.0579 (14)	0.0203 (13)	−0.0073 (13)	−0.0015 (11)
C12	0.0560 (13)	0.0474 (12)	0.0562 (13)	0.0057 (10)	−0.0110 (10)	−0.0070 (10)
C13	0.0585 (15)	0.101 (2)	0.090 (2)	−0.0091 (14)	−0.0240 (14)	−0.0389 (17)
C14	0.136 (3)	0.085 (2)	0.100 (3)	0.050 (2)	−0.041 (2)	0.0008 (19)
N1	0.0415 (9)	0.0426 (9)	0.0433 (9)	−0.0010 (7)	−0.0078 (7)	0.0007 (7)
N2	0.0507 (11)	0.0670 (13)	0.0716 (14)	−0.0038 (9)	−0.0350 (11)	0.0086 (10)
O1	0.0400 (7)	0.0664 (10)	0.0586 (9)	0.0051 (7)	−0.0254 (7)	−0.0112 (7)
O2	0.0451 (8)	0.0412 (8)	0.0708 (10)	−0.0064 (6)	−0.0158 (7)	−0.0025 (7)
O3	0.0671 (11)	0.1086 (16)	0.0516 (10)	−0.0154 (10)	−0.0196 (9)	0.0114 (10)
O4	0.1010 (17)	0.0670 (13)	0.147 (2)	0.0127 (12)	−0.0545 (16)	0.0241 (13)
S1	0.0304 (2)	0.0421 (3)	0.0500 (3)	−0.00165 (17)	−0.01472 (19)	−0.0047 (2)

C1—C6	1.383 (3)	C9—H9	0.9300
C1—C2	1.389 (3)	C10—C11	1.380 (4)
C1—S1	1.7764 (18)	C10—H10	0.9300
C2—C3	1.384 (3)	C11—C12	1.392 (3)
C2—N2	1.470 (3)	C11—C14	1.512 (4)
C3—C4	1.371 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.369 (4)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.383 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—C12	1.382 (3)	N1—S1	1.6049 (18)
C7—C8	1.397 (3)	N1—H1N	0.823 (16)
C7—N1	1.431 (3)	N2—O4	1.213 (3)
C8—C9	1.393 (4)	N2—O3	1.218 (3)
C8—C13	1.500 (4)	O1—S1	1.4242 (15)
C9—C10	1.367 (5)	O2—S1	1.4295 (15)
C6—C1—C2	118.12 (18)	C10—C11—C12	116.9 (3)
C6—C1—S1	117.31 (15)	C10—C11—C14	122.5 (3)
C2—C1—S1	124.57 (15)	C12—C11—C14	120.6 (3)
C3—C2—C1	121.6 (2)	C7—C12—C11	121.1 (2)
C3—C2—N2	116.78 (18)	C7—C12—H12	119.4
C1—C2—N2	121.63 (18)	C11—C12—H12	119.4
C4—C3—C2	119.0 (2)	C8—C13—H13A	109.5
C4—C3—H3	120.5	C8—C13—H13B	109.5
C2—C3—H3	120.5	H13A—C13—H13B	109.5
C5—C4—C3	120.4 (2)	C8—C13—H13C	109.5
C5—C4—H4	119.8	H13A—C13—H13C	109.5
C3—C4—H4	119.8	H13B—C13—H13C	109.5
C4—C5—C6	120.5 (2)	C11—C14—H14A	109.5
C4—C5—H5	119.7	C11—C14—H14B	109.5
C6—C5—H5	119.7	H14A—C14—H14B	109.5
C5—C6—C1	120.3 (2)	C11—C14—H14C	109.5
C5—C6—H6	119.9	H14A—C14—H14C	109.5
C1—C6—H6	119.9	H14B—C14—H14C	109.5
C12—C7—C8	121.8 (2)	C7—N1—S1	121.88 (14)
C12—C7—N1	117.78 (19)	C7—N1—H1N	119.0 (17)
C8—C7—N1	120.4 (2)	S1—N1—H1N	115.8 (17)
C9—C8—C7	116.1 (2)	O4—N2—O3	125.3 (2)
C9—C8—C13	121.2 (2)	O4—N2—C2	117.4 (2)
C7—C8—C13	122.6 (2)	O3—N2—C2	117.3 (2)
C10—C9—C8	121.9 (3)	O1—S1—O2	119.85 (9)
C10—C9—H9	119.1	O1—S1—N1	108.74 (9)
C8—C9—H9	119.1	O2—S1—N1	107.05 (9)
C9—C10—C11	122.1 (2)	O1—S1—C1	105.37 (9)
C9—C10—H10	118.9	O2—S1—C1	108.28 (9)
C11—C10—H10	118.9	N1—S1—C1	106.93 (9)
C6—C1—C2—C3	−0.9 (3)	C8—C7—C12—C11	1.7 (3)
S1—C1—C2—C3	178.74 (16)	N1—C7—C12—C11	−179.5 (2)
C6—C1—C2—N2	177.9 (2)	C10—C11—C12—C7	−2.4 (4)
S1—C1—C2—N2	−2.5 (3)	C14—C11—C12—C7	178.3 (2)
C1—C2—C3—C4	2.1 (3)	C12—C7—N1—S1	75.0 (2)
N2—C2—C3—C4	−176.8 (2)	C8—C7—N1—S1	−106.1 (2)
C2—C3—C4—C5	−1.2 (4)	C3—C2—N2—O4	−59.0 (3)
C3—C4—C5—C6	−0.8 (4)	C1—C2—N2—O4	122.2 (2)
C4—C5—C6—C1	2.0 (4)	C3—C2—N2—O3	118.6 (2)
C2—C1—C6—C5	−1.2 (3)	C1—C2—N2—O3	−60.2 (3)
S1—C1—C6—C5	179.19 (19)	C7—N1—S1—O1	−41.91 (18)
C12—C7—C8—C9	0.5 (3)	C7—N1—S1—O2	−172.73 (15)
N1—C7—C8—C9	−178.28 (19)	C7—N1—S1—C1	71.41 (18)
C12—C7—C8—C13	179.7 (2)	C6—C1—S1—O1	22.19 (19)
N1—C7—C8—C13	0.9 (3)	C2—C1—S1—O1	−157.44 (17)
C7—C8—C9—C10	−2.0 (4)	C6—C1—S1—O2	151.56 (17)
C13—C8—C9—C10	178.8 (2)	C2—C1—S1—O2	−28.1 (2)
C8—C9—C10—C11	1.3 (4)	C6—C1—S1—N1	−93.39 (18)
C9—C10—C11—C12	0.9 (4)	C2—C1—S1—N1	86.97 (18)
C9—C10—C11—C14	−179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.82 (2)	2.27 (2)	3.023 (2)	152 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.82 (2)	2.27 (2)	3.023 (2)	152 (2)

Symmetry code: (i) .