4-Methyl-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamo-yl]phen-yl}benzene-sulfonamide.

In the title compound, C(17)H(17)N(3)O(5)S(2), the dihedral angle between the two benzene rings is 81.27 (8)° and the heterocyclic ring is oriented at 9.1 (2) and 76.01 (9)° with respect to these rings. Mol-ecules are connected via N-H⋯N and N-H⋯O hydrogen bonds, generating an R(2) (2)(8) motif, into chains running along the [001] direction. There is also an intra-molecular C-H⋯O hydrogen bond completing an S(6) ring motif. The polymeric chains are inter-linked through inter-molecular C-H⋯O hydrogen bonds.

Related literature

For a related crystal structure, see: Ashfaq et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H17N3O5S2

M = 407.46

Monoclinic,

a = 10.6294 (6) Å

b = 12.2394 (7) Å

c = 14.9673 (11) Å

β = 106.863 (2)°

V = 1863.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.915, T max = 0.938

17943 measured reflections

4629 independent reflections

2488 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.141

S = 1.02

4629 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005260/gk2455sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005260/gk2455Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005260/gk2455Isup3.cml

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

C17H17N3O5S2	F(000) = 848
Mr = 407.46	Dx = 1.452 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2488 reflections
a = 10.6294 (6) Å	θ = 2.2–28.3°
b = 12.2394 (7) Å	µ = 0.32 mm−1
c = 14.9673 (11) Å	T = 296 K
β = 106.863 (2)°	Prism, colorless
V = 1863.5 (2) Å3	0.35 × 0.25 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4629 independent reflections
Radiation source: fine-focus sealed tube	2488 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 7.50 pixels mm-1	θmax = 28.3°, θmin = 2.2°
ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→16
Tmin = 0.915, Tmax = 0.938	l = −19→19
17943 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.1435P] where P = (Fo2 + 2Fc2)/3
4629 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.37 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 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	0.17178 (7)	0.12476 (6)	0.43330 (5)	0.0475 (3)
S2	0.42023 (7)	0.58034 (6)	0.24478 (5)	0.0485 (3)
O1	0.20899 (18)	0.03512 (15)	0.49755 (15)	0.0596 (8)
O2	0.09435 (18)	0.10311 (16)	0.33965 (14)	0.0575 (7)
O3	0.54004 (19)	0.62547 (15)	0.30218 (14)	0.0594 (7)
O4	0.30436 (19)	0.64578 (16)	0.21489 (15)	0.0642 (8)
O5	0.65024 (19)	0.33654 (16)	0.10010 (15)	0.0618 (8)
N1	0.3101 (2)	0.18092 (19)	0.43406 (16)	0.0519 (8)
N2	0.4456 (2)	0.53685 (18)	0.14776 (16)	0.0486 (8)
N3	0.5291 (2)	0.3918 (2)	0.08307 (18)	0.0605 (9)
C1	0.0863 (2)	0.2224 (2)	0.47933 (18)	0.0398 (8)
C2	−0.0473 (3)	0.2308 (3)	0.4409 (2)	0.0573 (11)
C3	−0.1174 (3)	0.3048 (3)	0.4774 (2)	0.0684 (14)
C4	−0.0567 (3)	0.3690 (3)	0.5522 (2)	0.0615 (12)
C5	0.0766 (4)	0.3572 (3)	0.5909 (3)	0.0703 (14)
C6	0.1495 (3)	0.2850 (3)	0.5556 (2)	0.0592 (11)
C7	−0.1339 (4)	0.4484 (3)	0.5932 (3)	0.1003 (19)
C8	0.3303 (2)	0.2762 (2)	0.38676 (19)	0.0440 (9)
C9	0.4465 (3)	0.3330 (3)	0.4242 (2)	0.0607 (11)
C10	0.4738 (3)	0.4247 (3)	0.3811 (2)	0.0578 (11)
C11	0.3859 (2)	0.4623 (2)	0.30027 (18)	0.0427 (9)
C12	0.2695 (3)	0.4061 (2)	0.2627 (2)	0.0509 (10)
C13	0.2425 (3)	0.3132 (2)	0.3054 (2)	0.0513 (10)
C14	0.5480 (3)	0.4644 (2)	0.14888 (19)	0.0430 (9)
C15	0.6744 (3)	0.4591 (2)	0.2104 (2)	0.0498 (10)
C16	0.7342 (3)	0.3799 (2)	0.1768 (2)	0.0482 (10)
C17	0.8701 (3)	0.3364 (3)	0.2031 (2)	0.0661 (11)
H1	0.37992	0.14872	0.46739	0.0623*
H2	−0.09040	0.18700	0.39052	0.0687*
H2A	0.39496	0.55907	0.09507	0.0583*
H3	−0.20773	0.31110	0.45045	0.0821*
H5	0.11898	0.39923	0.64258	0.0842*
H6	0.23972	0.27863	0.58283	0.0707*
H7A	−0.22555	0.42985	0.57205	0.1503*
H7B	−0.12163	0.52121	0.57344	0.1503*
H7C	−0.10358	0.44443	0.66009	0.1503*
H9	0.50638	0.30849	0.47898	0.0729*
H10	0.55227	0.46190	0.40663	0.0696*
H12	0.20926	0.43125	0.20833	0.0610*
H13	0.16469	0.27516	0.27928	0.0614*
H15	0.70953	0.50155	0.26337	0.0597*
H17A	0.90803	0.34876	0.15310	0.0992*
H17B	0.86837	0.25935	0.21492	0.0992*
H17C	0.92184	0.37272	0.25840	0.0992*

	U11	U22	U33	U12	U13	U23
S1	0.0381 (4)	0.0495 (4)	0.0522 (5)	0.0024 (3)	0.0088 (3)	−0.0024 (4)
S2	0.0440 (4)	0.0468 (4)	0.0504 (5)	0.0060 (3)	0.0071 (3)	−0.0020 (3)
O1	0.0506 (12)	0.0490 (12)	0.0743 (15)	0.0042 (10)	0.0104 (10)	0.0135 (11)
O2	0.0497 (11)	0.0649 (13)	0.0521 (13)	0.0017 (10)	0.0054 (10)	−0.0180 (10)
O3	0.0567 (12)	0.0535 (12)	0.0586 (14)	−0.0064 (10)	0.0019 (11)	−0.0103 (10)
O4	0.0588 (13)	0.0586 (13)	0.0694 (15)	0.0221 (11)	0.0095 (11)	0.0017 (11)
O5	0.0484 (12)	0.0645 (13)	0.0666 (15)	0.0060 (11)	0.0075 (11)	−0.0149 (11)
N1	0.0332 (12)	0.0610 (15)	0.0591 (16)	0.0086 (11)	0.0097 (11)	0.0108 (13)
N2	0.0456 (13)	0.0547 (14)	0.0425 (14)	0.0071 (12)	0.0083 (11)	0.0061 (11)
N3	0.0435 (14)	0.0665 (17)	0.0629 (18)	0.0073 (13)	0.0018 (13)	−0.0123 (14)
C1	0.0350 (14)	0.0425 (15)	0.0391 (15)	−0.0024 (12)	0.0063 (12)	−0.0003 (12)
C2	0.0443 (16)	0.074 (2)	0.0498 (19)	0.0014 (16)	0.0076 (14)	−0.0161 (16)
C3	0.0527 (19)	0.087 (3)	0.065 (2)	0.0168 (18)	0.0165 (17)	−0.005 (2)
C4	0.073 (2)	0.058 (2)	0.062 (2)	0.0090 (18)	0.0330 (19)	0.0019 (17)
C5	0.082 (3)	0.063 (2)	0.065 (2)	−0.014 (2)	0.020 (2)	−0.0241 (18)
C6	0.0465 (16)	0.066 (2)	0.059 (2)	−0.0070 (16)	0.0059 (15)	−0.0122 (17)
C7	0.128 (4)	0.084 (3)	0.105 (3)	0.030 (3)	0.059 (3)	−0.007 (2)
C8	0.0335 (14)	0.0518 (17)	0.0465 (17)	0.0084 (14)	0.0113 (13)	−0.0003 (14)
C9	0.0451 (17)	0.071 (2)	0.053 (2)	−0.0002 (16)	−0.0063 (15)	0.0160 (17)
C10	0.0416 (16)	0.068 (2)	0.054 (2)	−0.0052 (16)	−0.0018 (14)	0.0076 (17)
C11	0.0353 (14)	0.0511 (16)	0.0409 (16)	0.0056 (13)	0.0098 (12)	−0.0021 (13)
C12	0.0399 (16)	0.0602 (19)	0.0451 (17)	0.0064 (15)	0.0007 (14)	0.0041 (15)
C13	0.0353 (14)	0.061 (2)	0.0507 (18)	−0.0007 (14)	0.0017 (13)	−0.0019 (16)
C14	0.0414 (16)	0.0438 (16)	0.0438 (16)	−0.0055 (14)	0.0126 (13)	0.0034 (14)
C15	0.0392 (15)	0.0574 (19)	0.0480 (17)	−0.0066 (14)	0.0052 (14)	−0.0071 (15)
C16	0.0384 (15)	0.0499 (17)	0.0537 (19)	−0.0048 (14)	0.0094 (14)	0.0042 (15)
C17	0.0455 (17)	0.067 (2)	0.083 (2)	0.0075 (16)	0.0141 (17)	−0.0025 (18)

S1—O1	1.437 (2)	C8—C9	1.386 (4)
S1—O2	1.429 (2)	C9—C10	1.367 (5)
S1—N1	1.620 (2)	C10—C11	1.376 (4)
S1—C1	1.758 (3)	C11—C12	1.384 (4)
S2—O3	1.425 (2)	C12—C13	1.375 (4)
S2—O4	1.428 (2)	C14—C15	1.393 (4)
S2—N2	1.641 (2)	C15—C16	1.335 (4)
S2—C11	1.757 (3)	C16—C17	1.482 (5)
O5—N3	1.411 (3)	C2—H2	0.9300
O5—C16	1.342 (4)	C3—H3	0.9300
N1—C8	1.413 (3)	C5—H5	0.9300
N2—C14	1.400 (4)	C6—H6	0.9300
N3—C14	1.298 (4)	C7—H7A	0.9600
N1—H1	0.8600	C7—H7B	0.9600
N2—H2A	0.8600	C7—H7C	0.9600
C1—C2	1.373 (4)	C9—H9	0.9300
C1—C6	1.377 (4)	C10—H10	0.9300
C2—C3	1.382 (5)	C12—H12	0.9300
C3—C4	1.367 (4)	C13—H13	0.9300
C4—C7	1.512 (5)	C15—H15	0.9300
C4—C5	1.374 (5)	C17—H17A	0.9600
C5—C6	1.378 (5)	C17—H17B	0.9600
C8—C13	1.378 (4)	C17—H17C	0.9600
O1—S1—O2	118.90 (12)	C8—C13—C12	120.2 (3)
O1—S1—N1	104.26 (12)	N2—C14—N3	118.4 (3)
O1—S1—C1	109.27 (12)	N2—C14—C15	129.4 (2)
O2—S1—N1	110.41 (12)	N3—C14—C15	112.2 (3)
O2—S1—C1	107.11 (12)	C14—C15—C16	105.0 (3)
N1—S1—C1	106.26 (12)	O5—C16—C17	116.1 (2)
O3—S2—O4	120.68 (12)	C15—C16—C17	134.0 (3)
O3—S2—N2	108.17 (12)	O5—C16—C15	109.8 (3)
O3—S2—C11	107.80 (12)	C1—C2—H2	120.00
O4—S2—N2	104.65 (12)	C3—C2—H2	120.00
O4—S2—C11	109.32 (12)	C2—C3—H3	119.00
N2—S2—C11	105.17 (12)	C4—C3—H3	119.00
N3—O5—C16	108.1 (2)	C4—C5—H5	119.00
S1—N1—C8	128.05 (18)	C6—C5—H5	119.00
S2—N2—C14	121.44 (19)	C1—C6—H6	121.00
O5—N3—C14	105.0 (2)	C5—C6—H6	121.00
C8—N1—H1	116.00	C4—C7—H7A	109.00
S1—N1—H1	116.00	C4—C7—H7B	109.00
S2—N2—H2A	119.00	C4—C7—H7C	109.00
C14—N2—H2A	119.00	H7A—C7—H7B	109.00
S1—C1—C6	121.3 (2)	H7A—C7—H7C	109.00
C2—C1—C6	120.2 (3)	H7B—C7—H7C	110.00
S1—C1—C2	118.4 (2)	C8—C9—H9	120.00
C1—C2—C3	119.6 (3)	C10—C9—H9	120.00
C2—C3—C4	121.3 (3)	C9—C10—H10	120.00
C3—C4—C5	118.0 (3)	C11—C10—H10	120.00
C3—C4—C7	121.3 (3)	C11—C12—H12	120.00
C5—C4—C7	120.7 (3)	C13—C12—H12	120.00
C4—C5—C6	122.1 (4)	C8—C13—H13	120.00
C1—C6—C5	118.8 (3)	C12—C13—H13	120.00
N1—C8—C9	117.3 (2)	C14—C15—H15	128.00
N1—C8—C13	123.5 (2)	C16—C15—H15	128.00
C9—C8—C13	119.2 (3)	C16—C17—H17A	110.00
C8—C9—C10	120.5 (3)	C16—C17—H17B	109.00
C9—C10—C11	120.4 (3)	C16—C17—H17C	109.00
S2—C11—C12	120.0 (2)	H17A—C17—H17B	109.00
C10—C11—C12	119.3 (3)	H17A—C17—H17C	110.00
S2—C11—C10	120.6 (2)	H17B—C17—H17C	109.00
C11—C12—C13	120.3 (3)
O1—S1—N1—C8	−176.4 (2)	O5—N3—C14—C15	−1.4 (3)
O2—S1—N1—C8	54.8 (3)	S1—C1—C2—C3	178.3 (2)
C1—S1—N1—C8	−61.0 (3)	C6—C1—C2—C3	2.0 (5)
O1—S1—C1—C2	−106.2 (2)	S1—C1—C6—C5	−177.5 (3)
O1—S1—C1—C6	70.1 (3)	C2—C1—C6—C5	−1.3 (5)
O2—S1—C1—C2	23.9 (3)	C1—C2—C3—C4	−1.0 (5)
O2—S1—C1—C6	−159.9 (2)	C2—C3—C4—C5	−0.6 (5)
N1—S1—C1—C2	141.9 (2)	C2—C3—C4—C7	−178.8 (3)
N1—S1—C1—C6	−41.9 (3)	C3—C4—C5—C6	1.2 (6)
O3—S2—N2—C14	53.7 (2)	C7—C4—C5—C6	179.5 (3)
O4—S2—N2—C14	−176.5 (2)	C4—C5—C6—C1	−0.3 (5)
C11—S2—N2—C14	−61.3 (2)	N1—C8—C9—C10	178.7 (3)
O3—S2—C11—C10	−4.6 (3)	C13—C8—C9—C10	0.1 (5)
O3—S2—C11—C12	175.4 (2)	N1—C8—C13—C12	−179.3 (3)
O4—S2—C11—C10	−137.5 (2)	C9—C8—C13—C12	−0.8 (4)
O4—S2—C11—C12	42.5 (3)	C8—C9—C10—C11	0.4 (5)
N2—S2—C11—C10	110.6 (2)	C9—C10—C11—S2	179.8 (2)
N2—S2—C11—C12	−69.4 (2)	C9—C10—C11—C12	−0.2 (4)
C16—O5—N3—C14	0.7 (3)	S2—C11—C12—C13	179.5 (2)
N3—O5—C16—C15	0.4 (3)	C10—C11—C12—C13	−0.5 (4)
N3—O5—C16—C17	−176.7 (2)	C11—C12—C13—C8	1.0 (4)
S1—N1—C8—C9	154.9 (2)	N2—C14—C15—C16	−176.3 (3)
S1—N1—C8—C13	−26.6 (4)	N3—C14—C15—C16	1.6 (3)
S2—N2—C14—N3	145.2 (2)	C14—C15—C16—O5	−1.1 (3)
S2—N2—C14—C15	−37.0 (4)	C14—C15—C16—C17	175.2 (3)
O5—N3—C14—N2	176.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.86	2.04	2.859 (3)	159
N2—H2A···O1ii	0.86	2.39	2.979 (3)	127
C2—H2···O4iii	0.93	2.42	3.208 (4)	143
C13—H13···O2	0.93	2.49	3.134 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.86	2.04	2.859 (3)	159
N2—H2A⋯O1ii	0.86	2.39	2.979 (3)	127
C2—H2⋯O4iii	0.93	2.42	3.208 (4)	143
C13—H13⋯O2	0.93	2.49	3.134 (3)	126

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