N-(2,4-Dimethyl­phen­yl)-2-nitrobenzene­sulfonamide

The mol­ecular conformation of the title compound, C₁₄H₁₄N₂O₄S, is stabilized by an N—H...O hydrogen bond. The packing is influenced by π–π stacking inter­actions between nitro­phenyl rings [centroid-to-centroid separation 3.744 (13) Å].

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.102
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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S1. Comment

The molecular conformation of the title compound is stabilized by a N—H···O hydrogen bond. The dihedral angle between the xylene and nitrobenzen ring is 62.61 (10) °. The nitro group has an angle of 50.50 (12) ° with its connected benzene ring.

In the crystal of (I), aromatic π-π interaction [centroid separation = 3.744 (13) Å] between nitrobenzene rings (symmetry operator for the second ring 1/2-X, 3/2-Y, –Z) makes a great contribution to the packing. No significant intermolecular H-bonds were observed as reported in other N-arylbenzenesulfonamides.

Related literature

For N-arylbenzenesulfonamides, see: Shi (2007); Chang et al. (2007); Yu et al. (2007); Xing et al. (2006); Yu (2006); Xing & Zeng (2005).

S2. Experimental

The title compound was prepared according to the modified method of Shi (2007). Yellow blocks of the title compound were grown by evaporation of a MeOH-CH₂Cl₂ solution.

S3. Refinement

The N-bound H atoms were refined freely while the other H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C). The N—H distance was restrained to 0.86 (3) Å.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures

Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme and 30% probability displacement ellipsoids for the non-hydrogen atoms.

2-nitro-N-(2,4-dimethylphenyl)benzenesulfonamide

Crystal data

C14H14N2O4S	F(000) = 1280
Mr = 306.33	Dx = 1.432 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3333 reflections
a = 25.663 (4) Å	θ = 2.6–26.3°
b = 8.2546 (11) Å	µ = 0.25 mm^−1
c = 14.894 (2) Å	T = 294 K
β = 115.779 (2)°	Block, yellow
V = 2841.1 (7) Å^3	0.30 × 0.28 × 0.20 mm
Z = 8

Data collection

Bruker SMART 1K CCD area-detector diffractometer	2908 independent reflections
Radiation source: fine-focus sealed tube	2245 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→31
Tmin = 0.918, Tmax = 0.953	k = −10→6
7858 measured reflections	l = −17→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 1.9478P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.002
2908 reflections	Δρmax = 0.25 e Å^−3
197 parameters	Δρmin = −0.39 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0133 (7)

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	0.386258 (19)	0.71442 (6)	0.03736 (4)	0.04352 (17)
O1	0.41070 (6)	0.71700 (19)	0.14319 (11)	0.0610 (4)
O2	0.37524 (6)	0.86075 (17)	−0.01820 (13)	0.0647 (4)
O3	0.32493 (7)	0.6616 (2)	−0.19350 (12)	0.0742 (5)
O4	0.24466 (9)	0.7872 (3)	−0.23360 (15)	0.1012 (7)
N1	0.42726 (6)	0.60625 (19)	0.00522 (12)	0.0416 (4)
H1	0.4219 (9)	0.621 (3)	−0.0499 (14)	0.054 (7)*
N2	0.28263 (8)	0.6957 (2)	−0.18045 (13)	0.0582 (5)
C1	0.45760 (7)	0.4646 (2)	0.05671 (12)	0.0359 (4)
C2	0.50813 (7)	0.4835 (2)	0.14326 (13)	0.0423 (4)
H2	0.5203	0.5864	0.1693	0.051*
C3	0.54036 (8)	0.3492 (3)	0.19081 (14)	0.0491 (5)
H3	0.5742	0.3627	0.2492	0.059*
C4	0.52342 (8)	0.1959 (3)	0.15347 (15)	0.0492 (5)
C5	0.47274 (8)	0.1794 (2)	0.06744 (15)	0.0494 (5)
H5	0.4608	0.0761	0.0418	0.059*
C6	0.43880 (7)	0.3109 (2)	0.01757 (14)	0.0404 (4)
C7	0.55902 (12)	0.0497 (3)	0.2044 (2)	0.0782 (8)
H7A	0.5383	−0.0468	0.1728	0.117*
H7B	0.5664	0.0496	0.2733	0.117*
H7C	0.5951	0.0530	0.1995	0.117*
C8	0.38413 (9)	0.2852 (3)	−0.07680 (17)	0.0579 (6)
H8A	0.3894	0.3264	−0.1326	0.087*
H8B	0.3527	0.3413	−0.0719	0.087*
H8C	0.3755	0.1715	−0.0860	0.087*
C9	0.31865 (7)	0.6138 (2)	−0.00189 (13)	0.0378 (4)
C10	0.30726 (9)	0.5333 (2)	0.06886 (15)	0.0480 (5)
H10	0.3353	0.5304	0.1347	0.058*
C11	0.25484 (10)	0.4573 (3)	0.04321 (18)	0.0592 (6)
H11	0.2482	0.4012	0.0914	0.071*
C12	0.21268 (10)	0.4638 (3)	−0.05224 (19)	0.0609 (6)
H12	0.1773	0.4129	−0.0688	0.073*
C13	0.22224 (8)	0.5449 (3)	−0.12369 (16)	0.0549 (5)
H13	0.1933	0.5509	−0.1886	0.066*
C14	0.27490 (8)	0.6177 (2)	−0.09893 (13)	0.0422 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0382 (3)	0.0363 (3)	0.0528 (3)	−0.00032 (19)	0.0167 (2)	−0.0073 (2)
O1	0.0486 (8)	0.0741 (10)	0.0519 (8)	0.0006 (7)	0.0142 (7)	−0.0265 (7)
O2	0.0541 (8)	0.0360 (8)	0.1018 (12)	0.0017 (6)	0.0319 (8)	0.0053 (8)
O3	0.0621 (10)	0.1056 (14)	0.0635 (10)	0.0115 (9)	0.0354 (8)	0.0187 (9)
O4	0.0744 (12)	0.1410 (19)	0.0808 (13)	0.0417 (12)	0.0269 (10)	0.0620 (13)
N1	0.0402 (8)	0.0432 (9)	0.0430 (9)	0.0043 (7)	0.0197 (7)	0.0038 (7)
N2	0.0474 (10)	0.0746 (13)	0.0445 (9)	0.0060 (9)	0.0124 (8)	0.0118 (9)
C1	0.0314 (8)	0.0403 (9)	0.0387 (9)	0.0020 (7)	0.0178 (7)	0.0017 (7)
C2	0.0360 (9)	0.0511 (11)	0.0418 (10)	−0.0039 (8)	0.0190 (8)	−0.0076 (8)
C3	0.0355 (9)	0.0720 (14)	0.0366 (10)	0.0076 (9)	0.0127 (8)	0.0012 (9)
C4	0.0444 (10)	0.0575 (13)	0.0496 (11)	0.0124 (9)	0.0242 (9)	0.0103 (9)
C5	0.0490 (11)	0.0408 (11)	0.0616 (13)	0.0006 (8)	0.0270 (10)	0.0007 (9)
C6	0.0332 (8)	0.0424 (10)	0.0446 (10)	−0.0016 (7)	0.0160 (8)	−0.0014 (8)
C7	0.0756 (16)	0.0785 (18)	0.0764 (16)	0.0342 (14)	0.0291 (13)	0.0232 (14)
C8	0.0440 (11)	0.0509 (12)	0.0633 (13)	−0.0035 (9)	0.0089 (10)	−0.0113 (10)
C9	0.0370 (8)	0.0331 (9)	0.0442 (10)	0.0054 (7)	0.0184 (8)	−0.0025 (7)
C10	0.0537 (11)	0.0463 (11)	0.0460 (11)	0.0073 (9)	0.0236 (9)	0.0017 (9)
C11	0.0675 (14)	0.0487 (12)	0.0772 (15)	−0.0004 (10)	0.0460 (13)	0.0051 (11)
C12	0.0501 (12)	0.0517 (13)	0.0879 (17)	−0.0101 (10)	0.0365 (12)	−0.0113 (12)
C13	0.0407 (10)	0.0580 (12)	0.0581 (12)	−0.0007 (9)	0.0141 (9)	−0.0091 (10)
C14	0.0391 (9)	0.0424 (10)	0.0432 (10)	0.0050 (8)	0.0162 (8)	0.0009 (8)

Geometric parameters (Å, º)

S1—O1	1.4207 (15)	C5—H5	0.9300
S1—O2	1.4213 (16)	C6—C8	1.508 (3)
S1—N1	1.6037 (16)	C7—H7A	0.9600
S1—C9	1.7777 (18)	C7—H7B	0.9600
O3—N2	1.216 (2)	C7—H7C	0.9600
O4—N2	1.215 (2)	C8—H8A	0.9600
N1—C1	1.429 (2)	C8—H8B	0.9600
N1—H1	0.781 (18)	C8—H8C	0.9600
N2—C14	1.462 (3)	C9—C10	1.380 (3)
C1—C2	1.383 (2)	C9—C14	1.393 (2)
C1—C6	1.392 (2)	C10—C11	1.379 (3)
C2—C3	1.380 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.363 (3)
C3—C4	1.375 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.367 (3)
C4—C5	1.379 (3)	C12—H12	0.9300
C4—C7	1.504 (3)	C13—C14	1.375 (3)
C5—C6	1.388 (3)	C13—H13	0.9300
O1—S1—O2	120.87 (10)	C4—C7—H7A	109.5
O1—S1—N1	108.01 (9)	C4—C7—H7B	109.5
O2—S1—N1	106.84 (9)	H7A—C7—H7B	109.5
O1—S1—C9	105.58 (9)	C4—C7—H7C	109.5
O2—S1—C9	106.69 (9)	H7A—C7—H7C	109.5
N1—S1—C9	108.35 (8)	H7B—C7—H7C	109.5
C1—N1—S1	124.79 (13)	C6—C8—H8A	109.5
C1—N1—H1	120.1 (17)	C6—C8—H8B	109.5
S1—N1—H1	112.7 (16)	H8A—C8—H8B	109.5
O4—N2—O3	123.94 (19)	C6—C8—H8C	109.5
O4—N2—C14	117.07 (19)	H8A—C8—H8C	109.5
O3—N2—C14	118.93 (17)	H8B—C8—H8C	109.5
C2—C1—C6	120.47 (16)	C10—C9—C14	117.44 (17)
C2—C1—N1	118.61 (16)	C10—C9—S1	118.32 (14)
C6—C1—N1	120.81 (15)	C14—C9—S1	124.15 (14)
C3—C2—C1	119.81 (18)	C11—C10—C9	120.82 (19)
C3—C2—H2	120.1	C11—C10—H10	119.6
C1—C2—H2	120.1	C9—C10—H10	119.6
C4—C3—C2	121.23 (17)	C12—C11—C10	120.5 (2)
C4—C3—H3	119.4	C12—C11—H11	119.8
C2—C3—H3	119.4	C10—C11—H11	119.8
C3—C4—C5	118.10 (18)	C11—C12—C13	120.1 (2)
C3—C4—C7	121.3 (2)	C11—C12—H12	119.9
C5—C4—C7	120.6 (2)	C13—C12—H12	119.9
C4—C5—C6	122.60 (19)	C12—C13—C14	119.6 (2)
C4—C5—H5	118.7	C12—C13—H13	120.2
C6—C5—H5	118.7	C14—C13—H13	120.2
C5—C6—C1	117.78 (16)	C13—C14—C9	121.53 (18)
C5—C6—C8	120.11 (17)	C13—C14—N2	116.24 (17)
C1—C6—C8	122.10 (17)	C9—C14—N2	122.21 (16)
O1—S1—N1—C1	35.73 (17)	N1—S1—C9—C10	103.50 (15)
O2—S1—N1—C1	167.19 (14)	O1—S1—C9—C14	164.47 (15)
C9—S1—N1—C1	−78.19 (16)	O2—S1—C9—C14	34.70 (18)
S1—N1—C1—C2	−78.53 (19)	N1—S1—C9—C14	−80.02 (17)
S1—N1—C1—C6	105.39 (18)	C14—C9—C10—C11	1.3 (3)
C6—C1—C2—C3	0.4 (3)	S1—C9—C10—C11	178.03 (15)
N1—C1—C2—C3	−175.64 (16)	C9—C10—C11—C12	−1.7 (3)
C1—C2—C3—C4	0.4 (3)	C10—C11—C12—C13	0.5 (3)
C2—C3—C4—C5	−0.8 (3)	C11—C12—C13—C14	1.0 (3)
C2—C3—C4—C7	179.02 (19)	C12—C13—C14—C9	−1.4 (3)
C3—C4—C5—C6	0.3 (3)	C12—C13—C14—N2	177.30 (19)
C7—C4—C5—C6	−179.5 (2)	C10—C9—C14—C13	0.2 (3)
C4—C5—C6—C1	0.5 (3)	S1—C9—C14—C13	−176.31 (15)
C4—C5—C6—C8	179.36 (19)	C10—C9—C14—N2	−178.38 (17)
C2—C1—C6—C5	−0.9 (3)	S1—C9—C14—N2	5.1 (3)
N1—C1—C6—C5	175.14 (16)	O4—N2—C14—C13	49.3 (3)
C2—C1—C6—C8	−179.73 (18)	O3—N2—C14—C13	−128.1 (2)
N1—C1—C6—C8	−3.7 (3)	O4—N2—C14—C9	−132.0 (2)
O1—S1—C9—C10	−12.01 (17)	O3—N2—C14—C9	50.6 (3)
O2—S1—C9—C10	−141.79 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.78 (2)	2.50 (2)	3.017 (2)	125 (2)