N,4-Dimethyl-N-(4-nitro-benz-yl)benzene-sulfonamide.

In the title compound, C(15)H(16)N(2)O(4)S, there is a dihedral angle of 63.30 (8)° between the nitro-benzyl and benzene rings, which are separated by a sulfonamide unit The crystal packing is stabilized by a C-H⋯O inter-action.

Related literature

For the use of aromatic nitro and amine compounds as precursors in dye synthesis, see: Lauwiner et al. (1998 ▶); Yang et al. (2004 ▶). For the preparation of the title compound, see: Andersen et al. (1988 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H16N2O4S

M = 320.36

Monoclinic,

a = 9.5694 (19) Å

b = 6.1335 (12) Å

c = 26.126 (5) Å

β = 100.03 (3)°

V = 1510.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 113 (2) K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2003 ▶) T min = 0.955, T max = 0.977

8935 measured reflections

2661 independent reflections

2188 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.123

S = 1.10

2661 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku, 2003 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000330/sj2454sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000330/sj2454Isup2.hkl

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

C15H16N2O4S	F000 = 672
Mr = 320.36	Dx = 1.409 Mg m−3
Monoclinic, P21/c	Melting point = 403–404 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 9.5694 (19) Å	Cell parameters from 3609 reflections
b = 6.1335 (12) Å	θ = 2.2–27.9º
c = 26.126 (5) Å	µ = 0.23 mm−1
β = 100.03 (3)º	T = 113 (2) K
V = 1510.0 (5) Å3	Block, colorless
Z = 4	0.20 × 0.18 × 0.10 mm

Rigaku Saturn diffractometer	2661 independent reflections
Radiation source: fine-focus sealed tube	2188 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.057
Detector resolution: 7.31 pixels mm-1	θmax = 25.0º
T = 113(2) K	θmin = 2.2º
ω scans	h = −11→11
Absorption correction: multi-scan(CrystalClear; Rigaku, 2003)	k = −6→7
Tmin = 0.955, Tmax = 0.977	l = −31→26
8935 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0454P)2 + 1.1085P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2661 reflections	Δρmax = 0.36 e Å−3
201 parameters	Δρmin = −0.45 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S1	0.12405 (8)	0.46188 (11)	0.13266 (3)	0.0293 (2)
O1	0.0775 (3)	0.6688 (3)	0.14746 (9)	0.0531 (7)
O2	0.2167 (2)	0.4497 (4)	0.09498 (8)	0.0445 (6)
O3	−0.5173 (2)	−0.0352 (3)	−0.10469 (8)	0.0334 (5)
O4	−0.5383 (2)	−0.3199 (3)	−0.05751 (8)	0.0329 (5)
N1	−0.0187 (2)	0.3232 (3)	0.10887 (9)	0.0221 (5)
N2	−0.4801 (2)	−0.1489 (4)	−0.06589 (9)	0.0259 (5)
C1	0.2079 (3)	0.3328 (4)	0.19015 (11)	0.0210 (6)
C2	0.2046 (3)	0.4289 (5)	0.23762 (12)	0.0316 (7)
H2	0.1530	0.5601	0.2395	0.038*
C3	0.2765 (3)	0.3336 (5)	0.28224 (12)	0.0311 (7)
H3	0.2738	0.4004	0.3149	0.037*
C4	0.3529 (3)	0.1419 (4)	0.28053 (11)	0.0251 (6)
C5	0.3516 (3)	0.0458 (4)	0.23231 (12)	0.0285 (7)
H5	0.4007	−0.0878	0.2304	0.034*
C6	0.2809 (3)	0.1393 (4)	0.18703 (11)	0.0264 (6)
H6	0.2823	0.0723	0.1543	0.032*
C7	0.4382 (3)	0.0457 (5)	0.32894 (12)	0.0364 (8)
H7A	0.5367	0.0959	0.3327	0.055*
H7B	0.4356	−0.1137	0.3265	0.055*
H7C	0.3981	0.0922	0.3592	0.055*
C8	−0.1208 (3)	0.2999 (7)	0.14427 (14)	0.0496 (10)
H8A	−0.2139	0.2607	0.1244	0.074*
H8B	−0.1282	0.4381	0.1624	0.074*
H8C	−0.0886	0.1852	0.1697	0.074*
C9	0.0035 (3)	0.1211 (4)	0.08077 (12)	0.0282 (7)
H9A	0.0301	0.0020	0.1062	0.034*
H9B	0.0831	0.1428	0.0616	0.034*
C10	−0.1269 (3)	0.0558 (4)	0.04315 (11)	0.0222 (6)
C11	−0.1885 (3)	−0.1471 (4)	0.04786 (11)	0.0259 (6)
H11	−0.1499	−0.2403	0.0758	0.031*
C12	−0.3050 (3)	−0.2153 (4)	0.01256 (11)	0.0235 (6)
H12	−0.3473	−0.3534	0.0159	0.028*
C13	−0.3577 (3)	−0.0763 (4)	−0.02765 (11)	0.0215 (6)
C14	−0.2999 (3)	0.1272 (4)	−0.03363 (11)	0.0231 (6)
H14	−0.3386	0.2195	−0.0617	0.028*
C15	−0.1842 (3)	0.1921 (4)	0.00249 (11)	0.0223 (6)
H15	−0.1435	0.3317	−0.0006	0.027*

	U11	U22	U33	U12	U13	U23
S1	0.0358 (4)	0.0223 (4)	0.0238 (4)	−0.0080 (3)	−0.0117 (3)	0.0051 (3)
O1	0.0816 (18)	0.0182 (11)	0.0437 (16)	0.0046 (10)	−0.0330 (13)	−0.0008 (9)
O2	0.0393 (12)	0.0675 (16)	0.0242 (13)	−0.0274 (11)	−0.0015 (10)	0.0159 (11)
O3	0.0316 (11)	0.0426 (12)	0.0224 (12)	−0.0005 (9)	−0.0054 (9)	0.0013 (9)
O4	0.0290 (11)	0.0425 (12)	0.0269 (12)	−0.0163 (9)	0.0041 (9)	−0.0049 (9)
N1	0.0191 (11)	0.0236 (12)	0.0210 (14)	−0.0015 (9)	−0.0036 (10)	−0.0023 (9)
N2	0.0232 (12)	0.0347 (14)	0.0199 (14)	−0.0022 (10)	0.0039 (10)	−0.0082 (11)
C1	0.0172 (13)	0.0232 (14)	0.0192 (15)	−0.0034 (10)	−0.0060 (11)	0.0046 (11)
C2	0.0344 (16)	0.0269 (15)	0.0291 (18)	0.0094 (12)	−0.0067 (14)	−0.0033 (12)
C3	0.0319 (16)	0.0401 (17)	0.0188 (17)	0.0110 (13)	−0.0027 (13)	−0.0033 (13)
C4	0.0195 (13)	0.0292 (15)	0.0257 (17)	−0.0019 (11)	0.0018 (12)	0.0074 (12)
C5	0.0241 (14)	0.0258 (15)	0.0344 (19)	0.0062 (11)	0.0023 (13)	0.0022 (13)
C6	0.0255 (14)	0.0321 (15)	0.0212 (16)	0.0008 (12)	0.0034 (12)	−0.0032 (12)
C7	0.0321 (16)	0.0421 (18)	0.032 (2)	0.0049 (13)	−0.0044 (14)	0.0127 (14)
C8	0.0212 (16)	0.093 (3)	0.034 (2)	−0.0083 (17)	0.0030 (15)	−0.0152 (19)
C9	0.0248 (15)	0.0227 (14)	0.0340 (19)	0.0016 (11)	−0.0039 (13)	−0.0031 (12)
C10	0.0193 (13)	0.0219 (14)	0.0238 (16)	0.0008 (11)	−0.0006 (12)	−0.0048 (11)
C11	0.0250 (14)	0.0254 (14)	0.0252 (17)	0.0027 (11)	−0.0015 (12)	0.0026 (12)
C12	0.0225 (14)	0.0229 (14)	0.0255 (17)	−0.0025 (11)	0.0051 (12)	−0.0025 (11)
C13	0.0172 (13)	0.0271 (14)	0.0197 (16)	−0.0013 (10)	0.0016 (11)	−0.0069 (11)
C14	0.0219 (14)	0.0267 (14)	0.0202 (16)	0.0007 (11)	0.0025 (12)	0.0023 (11)
C15	0.0212 (14)	0.0194 (13)	0.0259 (17)	−0.0024 (10)	0.0033 (12)	−0.0015 (11)

S1—O1	1.421 (2)	C7—H7A	0.9800
S1—O2	1.437 (2)	C7—H7B	0.9800
S1—N1	1.637 (2)	C7—H7C	0.9800
S1—C1	1.762 (3)	C8—H8A	0.9800
O3—N2	1.231 (3)	C8—H8B	0.9800
O4—N2	1.225 (3)	C8—H8C	0.9800
N1—C8	1.464 (4)	C9—C10	1.502 (4)
N1—C9	1.475 (3)	C9—H9A	0.9900
N2—C13	1.470 (3)	C9—H9B	0.9900
C1—C2	1.378 (4)	C10—C15	1.387 (4)
C1—C6	1.387 (4)	C10—C11	1.392 (4)
C2—C3	1.376 (4)	C11—C12	1.382 (4)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.390 (4)	C12—C13	1.379 (4)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.389 (4)	C13—C14	1.385 (4)
C4—C7	1.502 (4)	C14—C15	1.382 (4)
C5—C6	1.381 (4)	C14—H14	0.9500
C5—H5	0.9500	C15—H15	0.9500
C6—H6	0.9500
O1—S1—O2	119.53 (15)	C4—C7—H7C	109.5
O1—S1—N1	106.68 (13)	H7A—C7—H7C	109.5
O2—S1—N1	106.66 (13)	H7B—C7—H7C	109.5
O1—S1—C1	106.68 (14)	N1—C8—H8A	109.5
O2—S1—C1	108.47 (13)	N1—C8—H8B	109.5
N1—S1—C1	108.43 (12)	H8A—C8—H8B	109.5
C8—N1—C9	113.7 (2)	N1—C8—H8C	109.5
C8—N1—S1	114.5 (2)	H8A—C8—H8C	109.5
C9—N1—S1	116.25 (17)	H8B—C8—H8C	109.5
O4—N2—O3	123.8 (2)	N1—C9—C10	112.0 (2)
O4—N2—C13	118.1 (2)	N1—C9—H9A	109.2
O3—N2—C13	118.0 (2)	C10—C9—H9A	109.2
C2—C1—C6	120.6 (3)	N1—C9—H9B	109.2
C2—C1—S1	119.8 (2)	C10—C9—H9B	109.2
C6—C1—S1	119.6 (2)	H9A—C9—H9B	107.9
C3—C2—C1	119.6 (3)	C15—C10—C11	119.3 (2)
C3—C2—H2	120.2	C15—C10—C9	120.9 (2)
C1—C2—H2	120.2	C11—C10—C9	119.8 (2)
C2—C3—C4	121.3 (3)	C12—C11—C10	121.1 (3)
C2—C3—H3	119.3	C12—C11—H11	119.5
C4—C3—H3	119.3	C10—C11—H11	119.5
C5—C4—C3	117.8 (3)	C13—C12—C11	117.9 (2)
C5—C4—C7	121.0 (3)	C13—C12—H12	121.1
C3—C4—C7	121.2 (3)	C11—C12—H12	121.1
C6—C5—C4	121.7 (3)	C12—C13—C14	122.9 (2)
C6—C5—H5	119.1	C12—C13—N2	118.3 (2)
C4—C5—H5	119.1	C14—C13—N2	118.9 (2)
C5—C6—C1	118.8 (3)	C15—C14—C13	118.1 (3)
C5—C6—H6	120.6	C15—C14—H14	121.0
C1—C6—H6	120.6	C13—C14—H14	121.0
C4—C7—H7A	109.5	C14—C15—C10	120.8 (2)
C4—C7—H7B	109.5	C14—C15—H15	119.6
H7A—C7—H7B	109.5	C10—C15—H15	119.6
O1—S1—N1—C8	−56.7 (3)	C2—C1—C6—C5	−0.7 (4)
O2—S1—N1—C8	174.5 (2)	S1—C1—C6—C5	177.0 (2)
C1—S1—N1—C8	57.9 (2)	C8—N1—C9—C10	66.9 (3)
O1—S1—N1—C9	167.4 (2)	S1—N1—C9—C10	−156.8 (2)
O2—S1—N1—C9	38.6 (2)	N1—C9—C10—C15	60.7 (3)
C1—S1—N1—C9	−78.0 (2)	N1—C9—C10—C11	−121.6 (3)
O1—S1—C1—C2	6.3 (3)	C15—C10—C11—C12	0.5 (4)
O2—S1—C1—C2	136.2 (2)	C9—C10—C11—C12	−177.3 (3)
N1—S1—C1—C2	−108.3 (2)	C10—C11—C12—C13	0.3 (4)
O1—S1—C1—C6	−171.4 (2)	C11—C12—C13—C14	−0.6 (4)
O2—S1—C1—C6	−41.4 (2)	C11—C12—C13—N2	179.0 (2)
N1—S1—C1—C6	74.0 (2)	O4—N2—C13—C12	7.1 (4)
C6—C1—C2—C3	1.1 (4)	O3—N2—C13—C12	−172.3 (2)
S1—C1—C2—C3	−176.6 (2)	O4—N2—C13—C14	−173.3 (2)
C1—C2—C3—C4	0.1 (5)	O3—N2—C13—C14	7.3 (4)
C2—C3—C4—C5	−1.6 (4)	C12—C13—C14—C15	0.0 (4)
C2—C3—C4—C7	176.3 (3)	N2—C13—C14—C15	−179.5 (2)
C3—C4—C5—C6	2.0 (4)	C13—C14—C15—C10	0.8 (4)
C7—C4—C5—C6	−175.9 (3)	C11—C10—C15—C14	−1.0 (4)
C4—C5—C6—C1	−0.9 (4)	C9—C10—C15—C14	176.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.99	2.32	3.287 (4)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.99	2.32	3.287 (4)	166

Symmetry code: (i) .