N-{4-[(5-Methyl-isoxazol-3-yl)sulfamo-yl]phen-yl}benzamide.

In the title compound, C(17)H(15)N(3)O(4)S, the five-membered isoxazole ring makes dihedral angles of 80.5 (2) and 81.3 (2)° with the two benzene rings, which form a dihedral angle of 39.81 (18)° with each other. A short intra-molecular C-H⋯O contact occurs. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds, which generate [001] chains, and further consolidated by weak C-H⋯O inter-actions.

Related literature

The N-alkyl­ated moiety is present in many natural products as well as in drugs, see: Wijayanti et al. (2010 ▶). For the synthesis and the biological properties of amide derivatives of sulfonamide-type drugs, see: Hussain (2009 ▶). For the crystal structures of similar sulfonamides, see: Shad et al. (2008 ▶, 2009 ▶); Chohan et al. (2008a ▶,b ▶); Tahir et al. (2008 ▶).

Experimental

Crystal data

C17H15N3O4S

M = 357.39

Monoclinic,

a = 8.2407 (6) Å

b = 23.5069 (16) Å

c = 8.5199 (6) Å

β = 92.155 (3)°

V = 1649.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.34 × 0.17 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

12756 measured reflections

2865 independent reflections

1544 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.135

S = 0.99

2865 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031132/hb5581sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031132/hb5581Isup2.hkl

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

C17H15N3O4S	F(000) = 744
Mr = 357.39	Dx = 1.439 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 886 reflections
a = 8.2407 (6) Å	θ = 2.5–19.0°
b = 23.5069 (16) Å	µ = 0.22 mm−1
c = 8.5199 (6) Å	T = 296 K
β = 92.155 (3)°	Block, off-white
V = 1649.3 (2) Å3	0.34 × 0.17 × 0.07 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1544 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.099
graphite	θmax = 25.0°, θmin = 2.5°
phi and ω scans	h = −9→9
12756 measured reflections	k = −27→27
2865 independent reflections	l = −9→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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0555P)2] where P = (Fo2 + 2Fc2)/3
2865 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.43740 (12)	0.83329 (4)	−0.22084 (11)	0.0386 (4)
O1	1.0003 (4)	0.81880 (17)	−0.0861 (4)	0.0844 (17)
O2	0.4214 (3)	0.77361 (9)	−0.1980 (3)	0.0496 (10)
O3	0.3429 (3)	0.86108 (10)	−0.3422 (3)	0.0496 (10)
O4	0.3631 (3)	1.03832 (10)	0.3334 (3)	0.0510 (10)
N1	0.8855 (5)	0.85441 (16)	−0.1611 (5)	0.0704 (17)
N2	0.6255 (4)	0.84586 (12)	−0.2644 (3)	0.0437 (11)
N3	0.3130 (4)	0.94599 (12)	0.3837 (3)	0.0404 (11)
C1	1.0426 (6)	0.7243 (2)	0.0112 (7)	0.108 (3)
C2	0.9324 (7)	0.7675 (2)	−0.0637 (5)	0.070 (2)
C3	0.7813 (6)	0.76770 (19)	−0.1215 (5)	0.0652 (19)
C4	0.7578 (5)	0.82254 (18)	−0.1798 (4)	0.0452 (16)
C5	0.4049 (4)	0.86758 (14)	−0.0421 (4)	0.0323 (12)
C6	0.3831 (4)	0.92538 (14)	−0.0387 (4)	0.0363 (12)
C7	0.3562 (4)	0.95266 (15)	0.0996 (4)	0.0372 (14)
C8	0.3494 (4)	0.92116 (15)	0.2385 (4)	0.0344 (12)
C9	0.3738 (5)	0.86339 (15)	0.2337 (4)	0.0414 (14)
C10	0.4019 (4)	0.83617 (15)	0.0942 (4)	0.0417 (14)
C11	0.3098 (4)	1.00198 (16)	0.4204 (4)	0.0364 (12)
C12	0.2330 (4)	1.01807 (15)	0.5708 (4)	0.0367 (12)
C13	0.2608 (5)	1.07230 (17)	0.6286 (4)	0.0495 (17)
C14	0.1852 (6)	1.09083 (19)	0.7601 (5)	0.0651 (19)
C15	0.0811 (5)	1.0556 (2)	0.8348 (5)	0.0610 (19)
C16	0.0515 (5)	1.00162 (19)	0.7787 (4)	0.0528 (17)
C17	0.1291 (4)	0.98271 (16)	0.6476 (4)	0.0430 (14)
H1A	1.09040	0.73950	0.10680	0.1620*
H1B	1.12680	0.71480	−0.05920	0.1620*
H1C	0.98170	0.69070	0.03430	0.1620*
H2N	0.64370	0.86780	−0.34260	0.0530*
H3	0.70730	0.73780	−0.12300	0.0780*
H3N	0.29020	0.92280	0.45780	0.0480*
H6	0.38660	0.94620	−0.13130	0.0430*
H7	0.34250	0.99190	0.10140	0.0450*
H9	0.37120	0.84230	0.32600	0.0500*
H10	0.41880	0.79710	0.09210	0.0500*
H13	0.33130	1.09640	0.57800	0.0600*
H14	0.20470	1.12730	0.79820	0.0780*
H15	0.03020	1.06810	0.92400	0.0730*
H16	−0.02050	0.97790	0.82880	0.0630*
H17	0.11110	0.94590	0.61100	0.0510*

	U11	U22	U33	U12	U13	U23
S1	0.0542 (7)	0.0308 (6)	0.0309 (6)	−0.0024 (5)	0.0013 (4)	−0.0030 (5)
O1	0.066 (3)	0.095 (3)	0.091 (3)	0.007 (2)	−0.0124 (19)	−0.007 (2)
O2	0.075 (2)	0.0238 (14)	0.0500 (18)	−0.0059 (13)	0.0019 (14)	−0.0043 (12)
O3	0.068 (2)	0.0470 (17)	0.0330 (16)	0.0020 (13)	−0.0096 (13)	0.0012 (13)
O4	0.078 (2)	0.0357 (16)	0.0409 (17)	−0.0104 (14)	0.0217 (14)	−0.0015 (13)
N1	0.057 (3)	0.063 (3)	0.090 (3)	0.003 (2)	−0.013 (2)	−0.007 (2)
N2	0.051 (2)	0.045 (2)	0.0359 (19)	0.0010 (16)	0.0138 (16)	0.0054 (15)
N3	0.059 (2)	0.0325 (19)	0.0302 (18)	0.0013 (15)	0.0085 (15)	0.0036 (14)
C1	0.067 (4)	0.142 (5)	0.116 (5)	0.039 (4)	0.008 (3)	0.046 (4)
C2	0.066 (4)	0.090 (4)	0.055 (3)	0.021 (3)	0.015 (3)	0.016 (3)
C3	0.049 (3)	0.068 (3)	0.079 (4)	0.009 (2)	0.006 (3)	0.023 (3)
C4	0.045 (3)	0.050 (3)	0.041 (2)	0.003 (2)	0.009 (2)	−0.010 (2)
C5	0.040 (2)	0.029 (2)	0.028 (2)	−0.0013 (17)	0.0020 (17)	0.0018 (17)
C6	0.041 (2)	0.039 (2)	0.029 (2)	−0.0008 (18)	0.0010 (17)	0.0069 (18)
C7	0.051 (3)	0.026 (2)	0.035 (2)	0.0019 (17)	0.0062 (18)	0.0030 (17)
C8	0.041 (2)	0.036 (2)	0.026 (2)	−0.0044 (17)	0.0004 (16)	0.0011 (17)
C9	0.061 (3)	0.029 (2)	0.034 (2)	−0.0002 (18)	0.0012 (19)	0.0085 (18)
C10	0.063 (3)	0.024 (2)	0.038 (2)	0.0000 (19)	0.0026 (19)	−0.0013 (18)
C11	0.037 (2)	0.040 (2)	0.032 (2)	0.0011 (18)	−0.0022 (17)	−0.0021 (19)
C12	0.035 (2)	0.046 (2)	0.029 (2)	0.0032 (18)	0.0004 (17)	0.0007 (18)
C13	0.054 (3)	0.050 (3)	0.045 (3)	−0.008 (2)	0.008 (2)	−0.008 (2)
C14	0.079 (4)	0.066 (3)	0.051 (3)	−0.003 (3)	0.011 (3)	−0.024 (3)
C15	0.066 (3)	0.077 (4)	0.041 (3)	0.008 (3)	0.015 (2)	−0.009 (3)
C16	0.049 (3)	0.071 (3)	0.039 (3)	0.005 (2)	0.008 (2)	0.005 (2)
C17	0.046 (3)	0.043 (2)	0.040 (2)	0.0046 (19)	0.000 (2)	−0.0013 (19)

S1—O2	1.423 (2)	C9—C10	1.377 (5)
S1—O3	1.429 (3)	C11—C12	1.499 (5)
S1—N2	1.634 (3)	C12—C17	1.376 (5)
S1—C5	1.753 (4)	C12—C13	1.383 (5)
O1—N1	1.400 (5)	C13—C14	1.373 (6)
O1—C2	1.346 (6)	C14—C15	1.367 (6)
O4—C11	1.223 (4)	C15—C16	1.375 (6)
N1—C4	1.297 (6)	C16—C17	1.381 (5)
N2—C4	1.396 (5)	C1—H1A	0.9600
N3—C8	1.410 (4)	C1—H1B	0.9600
N3—C11	1.353 (5)	C1—H1C	0.9600
N2—H2N	0.8600	C3—H3	0.9300
N3—H3N	0.8600	C6—H6	0.9300
C1—C2	1.490 (7)	C7—H7	0.9300
C2—C3	1.322 (7)	C9—H9	0.9300
C3—C4	1.392 (6)	C10—H10	0.9300
C5—C10	1.377 (5)	C13—H13	0.9300
C5—C6	1.371 (5)	C14—H14	0.9300
C6—C7	1.367 (5)	C15—H15	0.9300
C7—C8	1.399 (5)	C16—H16	0.9300
C8—C9	1.374 (5)	C17—H17	0.9300
O2—S1—O3	119.92 (15)	C11—C12—C13	117.9 (3)
O2—S1—N2	107.63 (15)	C11—C12—C17	123.0 (3)
O2—S1—C5	108.46 (16)	C13—C12—C17	119.0 (3)
O3—S1—N2	104.41 (15)	C12—C13—C14	120.6 (4)
O3—S1—C5	108.76 (16)	C13—C14—C15	120.0 (4)
N2—S1—C5	106.94 (15)	C14—C15—C16	120.3 (4)
N1—O1—C2	108.9 (4)	C15—C16—C17	119.8 (4)
O1—N1—C4	104.0 (3)	C12—C17—C16	120.4 (4)
S1—N2—C4	122.7 (2)	C2—C1—H1A	109.00
C8—N3—C11	127.7 (3)	C2—C1—H1B	110.00
C4—N2—H2N	119.00	C2—C1—H1C	109.00
S1—N2—H2N	119.00	H1A—C1—H1B	109.00
C8—N3—H3N	116.00	H1A—C1—H1C	109.00
C11—N3—H3N	116.00	H1B—C1—H1C	109.00
C1—C2—C3	135.4 (5)	C2—C3—H3	128.00
O1—C2—C3	109.6 (4)	C4—C3—H3	128.00
O1—C2—C1	114.9 (5)	C5—C6—H6	120.00
C2—C3—C4	104.6 (4)	C7—C6—H6	120.00
N1—C4—N2	116.8 (4)	C6—C7—H7	120.00
N1—C4—C3	112.9 (4)	C8—C7—H7	120.00
N2—C4—C3	130.0 (4)	C8—C9—H9	120.00
S1—C5—C6	119.9 (3)	C10—C9—H9	119.00
S1—C5—C10	119.6 (3)	C5—C10—H10	120.00
C6—C5—C10	120.5 (3)	C9—C10—H10	120.00
C5—C6—C7	120.6 (3)	C12—C13—H13	120.00
C6—C7—C8	119.6 (3)	C14—C13—H13	120.00
N3—C8—C7	122.7 (3)	C13—C14—H14	120.00
N3—C8—C9	118.1 (3)	C15—C14—H14	120.00
C7—C8—C9	119.2 (3)	C14—C15—H15	120.00
C8—C9—C10	121.0 (3)	C16—C15—H15	120.00
C5—C10—C9	119.2 (3)	C15—C16—H16	120.00
O4—C11—C12	121.0 (3)	C17—C16—H16	120.00
N3—C11—C12	117.1 (3)	C12—C17—H17	120.00
O4—C11—N3	121.9 (3)	C16—C17—H17	120.00
O2—S1—N2—C4	−47.0 (3)	C2—C3—C4—N2	174.6 (4)
O3—S1—N2—C4	−175.5 (3)	S1—C5—C6—C7	179.4 (3)
C5—S1—N2—C4	69.4 (3)	C10—C5—C6—C7	−0.8 (5)
O2—S1—C5—C6	−167.7 (3)	S1—C5—C10—C9	−179.0 (3)
O2—S1—C5—C10	12.5 (3)	C6—C5—C10—C9	1.2 (5)
O3—S1—C5—C6	−35.7 (3)	C5—C6—C7—C8	−0.6 (5)
O3—S1—C5—C10	144.5 (3)	C6—C7—C8—N3	−176.3 (3)
N2—S1—C5—C6	76.5 (3)	C6—C7—C8—C9	1.5 (5)
N2—S1—C5—C10	−103.3 (3)	N3—C8—C9—C10	176.8 (3)
C2—O1—N1—C4	−0.4 (5)	C7—C8—C9—C10	−1.1 (6)
N1—O1—C2—C1	178.2 (4)	C8—C9—C10—C5	−0.2 (6)
N1—O1—C2—C3	0.8 (5)	O4—C11—C12—C13	−16.4 (5)
O1—N1—C4—N2	−175.0 (3)	O4—C11—C12—C17	159.5 (3)
O1—N1—C4—C3	0.0 (5)	N3—C11—C12—C13	165.4 (3)
S1—N2—C4—N1	−143.7 (3)	N3—C11—C12—C17	−18.7 (5)
S1—N2—C4—C3	42.4 (5)	C11—C12—C13—C14	175.7 (4)
C11—N3—C8—C7	−13.4 (6)	C17—C12—C13—C14	−0.4 (6)
C11—N3—C8—C9	168.7 (4)	C11—C12—C17—C16	−174.6 (3)
C8—N3—C11—O4	−11.1 (6)	C13—C12—C17—C16	1.2 (5)
C8—N3—C11—C12	167.0 (3)	C12—C13—C14—C15	−0.2 (7)
O1—C2—C3—C4	−0.7 (5)	C13—C14—C15—C16	−0.1 (7)
C1—C2—C3—C4	−177.5 (5)	C14—C15—C16—C17	0.9 (6)
C2—C3—C4—N1	0.5 (5)	C15—C16—C17—C12	−1.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4i	0.86	2.21	2.788 (4)	124
N3—H3N···O3ii	0.86	2.27	3.075 (4)	156
C7—H7···O4	0.93	2.26	2.832 (4)	119
C10—H10···O2iii	0.93	2.44	3.130 (4)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O4i	0.86	2.21	2.788 (4)	124
N3—H3N⋯O3ii	0.86	2.27	3.075 (4)	156
C7—H7⋯O4	0.93	2.26	2.832 (4)	119
C10—H10⋯O2iii	0.93	2.44	3.130 (4)	131

Symmetry codes: (i) ; (ii) ; (iii) .