N-(2,5-Dimethoxy-phen-yl)-4-nitro-benzene-sulfonamide.

The title compound, C(14)H(14)N(2)O(6)S, is an inter-mediate for the synthesis of β-3-adrenergic receptor agonists. The two meth-oxy groups are approximately coplanar with the attached benzene ring [C-O-C-C = -2.7 (4) and 9.4 (4)°]. The dihedral angle between the two aromatic rings is 67.16 (12)°. An intra-molecular N-H⋯O hydrogen bond is observed. In the crystal, mol-ecules are linked into chains along the c axis by C-H⋯O hydrogen bonds.

Related literature

For biological activity of β-3-adrenergic receptors, see: Bardou et al. (1998 ▶); Hu et al. (2001 ▶); Klaus et al. (2001 ▶); Margareto et al. (2001 ▶); Ok et al. (2000 ▶); Parmee et al. (1998 ▶, 2000 ▶); Tonello et al. (1998 ▶); Weber et al. (1998 ▶).

Experimental

Crystal data

C14H14N2O6S

M = 338.33

Orthorhombic,

a = 14.532 (4) Å

b = 12.375 (4) Å

c = 17.311 (4) Å

V = 3113.2 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 292 K

0.48 × 0.44 × 0.42 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: for a sphere (WinGX; Farrugia, 1999 ▶) T min = 0.893, T max = 0.906

4003 measured reflections

2877 independent reflections

1790 reflections with I > 2σ(I)

R int = 0.004

3 standard reflections every 200 reflections intensity decay: 0.9%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.121

S = 1.06

2877 reflections

214 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.32 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027962/ci2846sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027962/ci2846Isup2.hkl

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

C14H14N2O6S	F(000) = 1408
Mr = 338.33	Dx = 1.444 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 32 reflections
a = 14.532 (4) Å	θ = 4.3–7.5°
b = 12.375 (4) Å	µ = 0.24 mm−1
c = 17.311 (4) Å	T = 292 K
V = 3113.2 (14) Å3	Block, colourless
Z = 8	0.48 × 0.44 × 0.42 mm

Enraf–Nonius CAD-4 diffractometer	1790 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.004
graphite	θmax = 25.4°, θmin = 2.4°
ω/2θ scans	h = −17→10
Absorption correction: for a sphere (WinGX; Farrugia, 1999)	k = −2→14
Tmin = 0.893, Tmax = 0.906	l = −11→20
4003 measured reflections	3 standard reflections every 200 reflections
2877 independent reflections	intensity decay: 0.9%

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)] = 0.040	Hydrogen site location: mixed
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.3387P] where P = (Fo2 + 2Fc2)/3
2877 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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	0.06666 (4)	0.69183 (6)	0.38224 (3)	0.0473 (2)
N1	0.05816 (14)	0.7151 (2)	0.28983 (13)	0.0530 (6)
H1N	0.0834 (18)	0.669 (2)	0.2672 (16)	0.057 (10)*
N2	−0.23262 (16)	0.3748 (2)	0.44664 (14)	0.0662 (7)
O1	−0.20633 (15)	0.94720 (18)	0.27633 (11)	0.0854 (7)
O2	0.00947 (13)	0.61834 (17)	0.16246 (10)	0.0731 (6)
O3	0.15329 (11)	0.63919 (17)	0.39190 (10)	0.0624 (5)
O4	0.04683 (13)	0.78981 (14)	0.42213 (10)	0.0615 (5)
O5	−0.30528 (13)	0.40717 (19)	0.47199 (13)	0.0831 (7)
O6	−0.21642 (16)	0.28124 (19)	0.43150 (18)	0.1057 (9)
C1	−0.02551 (15)	0.7501 (2)	0.25371 (14)	0.0452 (6)
C2	−0.07889 (17)	0.8326 (2)	0.28188 (15)	0.0549 (7)
H2	−0.0618	0.8681	0.3270	0.066*
C3	−0.15884 (18)	0.8634 (2)	0.24300 (15)	0.0569 (7)
C4	−0.18336 (17)	0.8124 (2)	0.17588 (15)	0.0562 (7)
H4	−0.2366	0.8329	0.1499	0.067*
C5	−0.12900 (19)	0.7305 (2)	0.14695 (15)	0.0576 (7)
H5	−0.1456	0.6966	0.1011	0.069*
C6	−0.04991 (17)	0.6982 (2)	0.18527 (14)	0.0495 (6)
C7	−0.2851 (2)	0.9874 (3)	0.23675 (18)	0.0916 (11)
H7A	−0.2688	1.0047	0.1844	0.137*
H7B	−0.3071	1.0512	0.2623	0.137*
H7C	−0.3325	0.9334	0.2368	0.137*
C8	−0.0013 (2)	0.5726 (3)	0.08822 (16)	0.0856 (11)
H8A	−0.0571	0.5312	0.0866	0.128*
H8B	0.0501	0.5263	0.0772	0.128*
H8C	−0.0041	0.6292	0.0504	0.128*
C9	−0.02178 (15)	0.59843 (19)	0.40462 (12)	0.0392 (5)
C10	−0.00660 (16)	0.4902 (2)	0.39088 (14)	0.0518 (6)
H10	0.0498	0.4670	0.3716	0.062*
C11	−0.07563 (18)	0.4167 (2)	0.40591 (15)	0.0542 (7)
H11	−0.0664	0.3432	0.3978	0.065*
C12	−0.15815 (16)	0.4544 (2)	0.43310 (14)	0.0474 (6)
C13	−0.17421 (17)	0.5610 (2)	0.44706 (15)	0.0536 (7)
H13	−0.2310	0.5838	0.4657	0.064*
C14	−0.10508 (15)	0.6342 (2)	0.43313 (15)	0.0494 (6)
H14	−0.1144	0.7073	0.4428	0.059*

	U11	U22	U33	U12	U13	U23
S1	0.0389 (3)	0.0590 (4)	0.0440 (3)	−0.0088 (3)	−0.0050 (3)	0.0049 (3)
N1	0.0418 (12)	0.0706 (17)	0.0467 (12)	−0.0002 (12)	0.0015 (9)	0.0032 (12)
N2	0.0512 (15)	0.0693 (18)	0.0780 (16)	−0.0135 (13)	−0.0120 (12)	0.0180 (14)
O1	0.0911 (14)	0.0898 (16)	0.0751 (13)	0.0359 (14)	−0.0083 (11)	−0.0015 (12)
O2	0.0859 (14)	0.0786 (14)	0.0547 (12)	0.0178 (12)	−0.0074 (10)	−0.0102 (11)
O3	0.0344 (9)	0.0884 (14)	0.0645 (11)	−0.0040 (9)	−0.0062 (8)	0.0152 (10)
O4	0.0738 (12)	0.0565 (11)	0.0541 (11)	−0.0146 (10)	−0.0101 (9)	−0.0053 (10)
O5	0.0478 (11)	0.0999 (18)	0.1017 (16)	−0.0122 (12)	0.0057 (11)	0.0330 (14)
O6	0.0880 (17)	0.0563 (15)	0.173 (3)	−0.0261 (13)	−0.0048 (17)	0.0040 (16)
C1	0.0409 (12)	0.0526 (14)	0.0422 (12)	−0.0101 (13)	−0.0033 (11)	0.0099 (13)
C2	0.0566 (15)	0.0624 (18)	0.0458 (13)	−0.0020 (14)	−0.0048 (12)	0.0002 (13)
C3	0.0563 (15)	0.0618 (17)	0.0525 (15)	0.0030 (14)	0.0020 (12)	0.0101 (14)
C4	0.0475 (14)	0.0632 (18)	0.0577 (15)	−0.0060 (14)	−0.0077 (12)	0.0131 (15)
C5	0.0602 (17)	0.0620 (18)	0.0505 (15)	−0.0190 (15)	−0.0130 (12)	0.0054 (14)
C6	0.0533 (14)	0.0506 (15)	0.0446 (13)	−0.0061 (13)	0.0019 (11)	0.0057 (13)
C7	0.082 (2)	0.105 (3)	0.088 (2)	0.036 (2)	0.0062 (18)	0.030 (2)
C8	0.128 (3)	0.078 (2)	0.0505 (17)	0.016 (2)	−0.0012 (17)	−0.0066 (17)
C9	0.0350 (12)	0.0436 (13)	0.0389 (12)	0.0026 (11)	−0.0008 (9)	0.0004 (11)
C10	0.0390 (12)	0.0553 (16)	0.0612 (16)	0.0061 (12)	0.0085 (11)	−0.0058 (13)
C11	0.0547 (15)	0.0425 (14)	0.0653 (16)	0.0039 (13)	0.0012 (12)	−0.0019 (13)
C12	0.0391 (13)	0.0484 (15)	0.0548 (14)	−0.0044 (12)	−0.0053 (11)	0.0091 (12)
C13	0.0360 (13)	0.0545 (16)	0.0703 (17)	0.0073 (12)	0.0093 (12)	0.0041 (14)
C14	0.0427 (13)	0.0409 (14)	0.0646 (15)	0.0075 (12)	0.0074 (12)	0.0013 (13)

S1—O4	1.4249 (19)	C4—H4	0.93
S1—O3	1.4273 (18)	C5—C6	1.386 (3)
S1—N1	1.630 (2)	C5—H5	0.93
S1—C9	1.771 (2)	C7—H7A	0.96
N1—C1	1.434 (3)	C7—H7B	0.96
N1—H1N	0.78 (3)	C7—H7C	0.96
N2—O6	1.210 (3)	C8—H8A	0.96
N2—O5	1.212 (3)	C8—H8B	0.96
N2—C12	1.482 (3)	C8—H8C	0.96
O1—C3	1.373 (3)	C9—C10	1.378 (4)
O1—C7	1.424 (3)	C9—C14	1.380 (3)
O2—C6	1.370 (3)	C10—C11	1.379 (3)
O2—C8	1.413 (3)	C10—H10	0.93
C1—C2	1.372 (3)	C11—C12	1.371 (3)
C1—C6	1.393 (3)	C11—H11	0.93
C2—C3	1.396 (3)	C12—C13	1.360 (3)
C2—H2	0.93	C13—C14	1.374 (3)
C3—C4	1.370 (4)	C13—H13	0.93
C4—C5	1.379 (4)	C14—H14	0.93
O4—S1—O3	120.67 (12)	C5—C6—C1	119.0 (2)
O4—S1—N1	108.06 (13)	O1—C7—H7A	109.5
O3—S1—N1	105.22 (11)	O1—C7—H7B	109.5
O4—S1—C9	107.61 (11)	H7A—C7—H7B	109.5
O3—S1—C9	108.45 (11)	O1—C7—H7C	109.5
N1—S1—C9	105.95 (11)	H7A—C7—H7C	109.5
C1—N1—S1	123.06 (17)	H7B—C7—H7C	109.5
C1—N1—H1N	114 (2)	O2—C8—H8A	109.5
S1—N1—H1N	109 (2)	O2—C8—H8B	109.5
O6—N2—O5	124.4 (3)	H8A—C8—H8B	109.5
O6—N2—C12	117.4 (3)	O2—C8—H8C	109.5
O5—N2—C12	118.3 (3)	H8A—C8—H8C	109.5
C3—O1—C7	117.8 (2)	H8B—C8—H8C	109.5
C6—O2—C8	118.8 (2)	C10—C9—C14	120.9 (2)
C2—C1—C6	120.1 (2)	C10—C9—S1	118.70 (18)
C2—C1—N1	123.3 (2)	C14—C9—S1	120.34 (19)
C6—C1—N1	116.6 (2)	C9—C10—C11	119.5 (2)
C1—C2—C3	120.2 (2)	C9—C10—H10	120.3
C1—C2—H2	119.9	C11—C10—H10	120.3
C3—C2—H2	119.9	C12—C11—C10	118.4 (2)
C4—C3—O1	125.0 (2)	C12—C11—H11	120.8
C4—C3—C2	120.0 (3)	C10—C11—H11	120.8
O1—C3—C2	115.0 (2)	C13—C12—C11	122.8 (2)
C3—C4—C5	119.9 (2)	C13—C12—N2	119.4 (2)
C3—C4—H4	120.1	C11—C12—N2	117.8 (2)
C5—C4—H4	120.1	C12—C13—C14	118.9 (2)
C4—C5—C6	120.9 (2)	C12—C13—H13	120.6
C4—C5—H5	119.6	C14—C13—H13	120.6
C6—C5—H5	119.6	C13—C14—C9	119.5 (2)
O2—C6—C5	126.3 (2)	C13—C14—H14	120.3
O2—C6—C1	114.7 (2)	C9—C14—H14	120.3
O4—S1—N1—C1	−61.0 (2)	N1—C1—C6—C5	−178.5 (2)
O3—S1—N1—C1	168.9 (2)	O4—S1—C9—C10	−162.61 (19)
C9—S1—N1—C1	54.1 (2)	O3—S1—C9—C10	−30.5 (2)
S1—N1—C1—C2	47.4 (3)	N1—S1—C9—C10	82.0 (2)
S1—N1—C1—C6	−134.8 (2)	O4—S1—C9—C14	19.3 (2)
C6—C1—C2—C3	1.3 (4)	O3—S1—C9—C14	151.32 (19)
N1—C1—C2—C3	179.0 (2)	N1—S1—C9—C14	−96.1 (2)
C7—O1—C3—C4	−2.7 (4)	C14—C9—C10—C11	−0.1 (4)
C7—O1—C3—C2	175.8 (3)	S1—C9—C10—C11	−178.18 (19)
C1—C2—C3—C4	−1.0 (4)	C9—C10—C11—C12	1.0 (4)
C1—C2—C3—O1	−179.7 (2)	C10—C11—C12—C13	−1.1 (4)
O1—C3—C4—C5	178.6 (2)	C10—C11—C12—N2	178.1 (2)
C2—C3—C4—C5	0.1 (4)	O6—N2—C12—C13	178.0 (3)
C3—C4—C5—C6	0.6 (4)	O5—N2—C12—C13	−2.0 (4)
C8—O2—C6—C5	9.4 (4)	O6—N2—C12—C11	−1.3 (4)
C8—O2—C6—C1	−170.3 (2)	O5—N2—C12—C11	178.7 (2)
C4—C5—C6—O2	−180.0 (2)	C11—C12—C13—C14	0.2 (4)
C4—C5—C6—C1	−0.3 (4)	N2—C12—C13—C14	−179.0 (2)
C2—C1—C6—O2	179.1 (2)	C12—C13—C14—C9	0.7 (4)
N1—C1—C6—O2	1.2 (3)	C10—C9—C14—C13	−0.8 (4)
C2—C1—C6—C5	−0.7 (4)	S1—C9—C14—C13	177.25 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.78 (3)	2.20 (3)	2.607 (3)	113 (2)
C8—H8C···O4i	0.96	2.55	3.414 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.78 (3)	2.20 (3)	2.607 (3)	113 (2)
C8—H8C⋯O4i	0.96	2.55	3.414 (4)	150

Symmetry code: (i) .