N,N-Bis(2-hy-droxy-eth-yl)-4-methyl-benzene-sulfonamide.

In the title compound C(11)H(17)NO(4)S, an intra-molecular O-H⋯O hydrogen bond forms an S(8) ring and determines the conformation of the bis-(2-hy-droxy-eth-yl) segment of the mol-ecule, holding the two CH(2)CH(2)OH groups close to coplanar (r.m.s. deviation = 0.185 Å). In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into zigzag chains along the b axis. Weaker additional C-H⋯O and C-H⋯π contacts generate a three dimensional network, with mol-ecules stacked along the b-axis direction.

Related literature

For pharmaceutical background to sulfonamides, see: Casini et al. (2002 ▶); Chambers & Jawetz (1998 ▶). For an alternative synthesis, see: Hori et al. (2011 ▶). For a related structure, see: Yoon et al. (2001 ▶). For standard bond lengths, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H17NO4S

M = 259.32

Orthorhombic,

a = 17.9308 (5) Å

b = 7.1881 (2) Å

c = 19.8333 (6) Å

V = 2556.28 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

3124 measured reflections

3124 independent reflections

2343 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.161

S = 0.99

3124 reflections

161 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT (Bruker, 2007 ▶); 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 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, ORTEP-3 (Farrugia, 1997 ▶), enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812041682/nk2181sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041682/nk2181Isup2.hkl

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

C11H17NO4S	F(000) = 1104
Mr = 259.32	Dx = 1.348 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4787 reflections
a = 17.9308 (5) Å	θ = 2.3–27.7°
b = 7.1881 (2) Å	µ = 0.26 mm−1
c = 19.8333 (6) Å	T = 296 K
V = 2556.28 (13) Å3	Block, colourless
Z = 8	0.16 × 0.12 × 0.10 mm

Bruker Kappa APEXII CCD diffractometer	2343 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 28.3°, θmin = 3.1°
φ and ω scans	h = 0→23
3124 measured reflections	k = 0→9
3124 independent reflections	l = 0→25

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0948P)2 + 1.0844P] where P = (Fo2 + 2Fc2)/3
3124 reflections	(Δ/σ)max = 0.009
161 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.39 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
O1	0.20186 (10)	0.1722 (3)	0.09437 (9)	0.0733 (6)
O2	0.08536 (10)	0.0146 (2)	0.06009 (8)	0.0598 (4)
S1	0.13232 (3)	0.17523 (7)	0.05993 (3)	0.04344 (19)
C1	0.15067 (10)	0.2344 (3)	−0.02460 (10)	0.0382 (4)
C2	0.21585 (12)	0.3277 (3)	−0.04138 (12)	0.0501 (5)
H2	0.2511	0.3542	−0.0084	0.060*
C3	0.22799 (14)	0.3806 (3)	−0.10709 (13)	0.0575 (6)
H3	0.2716	0.4437	−0.1181	0.069*
C4	0.17630 (14)	0.3417 (3)	−0.15754 (12)	0.0529 (6)
C7	0.1893 (2)	0.4011 (5)	−0.22931 (15)	0.0846 (9)
H7A	0.2302	0.3318	−0.2478	0.127*
H7B	0.2008	0.5315	−0.2305	0.127*
H7C	0.1452	0.3778	−0.2554	0.127*
C5	0.11233 (13)	0.2452 (3)	−0.13986 (11)	0.0501 (5)
H5	0.0777	0.2156	−0.1731	0.060*
C6	0.09883 (11)	0.1920 (3)	−0.07401 (10)	0.0420 (4)
H6	0.0553	0.1284	−0.0630	0.050*
N1	0.08353 (9)	0.3445 (2)	0.09165 (9)	0.0429 (4)
C8	0.00254 (12)	0.3381 (3)	0.08243 (11)	0.0495 (5)
H8A	−0.0087	0.2717	0.0411	0.059*
H8B	−0.0162	0.4640	0.0777	0.059*
C9	−0.03700 (14)	0.2449 (4)	0.14009 (13)	0.0635 (7)
H9A	−0.0899	0.2359	0.1302	0.076*
H9B	−0.0177	0.1200	0.1460	0.076*
O3	−0.02636 (12)	0.3483 (3)	0.19990 (9)	0.0680 (6)
H3O	−0.036 (2)	0.286 (6)	0.2288 (19)	0.102*
C10	0.11973 (15)	0.5289 (3)	0.09459 (12)	0.0600 (7)
H10A	0.1681	0.5203	0.0729	0.072*
H10B	0.0899	0.6163	0.0689	0.072*
C11	0.12997 (17)	0.6026 (5)	0.16224 (16)	0.0775 (9)
H11A	0.1668	0.5252	0.1844	0.093*
H11B	0.1518	0.7254	0.1576	0.093*
O4	0.07285 (19)	0.6183 (4)	0.20375 (14)	0.1263 (13)
H4O	0.049 (3)	0.532 (10)	0.207 (3)	0.190*

	U11	U22	U33	U12	U13	U23
O1	0.0538 (10)	0.1121 (17)	0.0539 (10)	0.0251 (9)	−0.0090 (8)	−0.0026 (10)
O2	0.0809 (11)	0.0353 (8)	0.0632 (10)	0.0006 (7)	0.0116 (8)	0.0062 (7)
S1	0.0454 (3)	0.0439 (3)	0.0411 (3)	0.00854 (19)	0.0022 (2)	−0.0011 (2)
C1	0.0384 (9)	0.0358 (9)	0.0404 (10)	0.0034 (7)	0.0051 (8)	−0.0069 (8)
C2	0.0441 (11)	0.0514 (12)	0.0548 (13)	−0.0088 (9)	0.0050 (9)	−0.0136 (10)
C3	0.0587 (13)	0.0475 (12)	0.0664 (15)	−0.0128 (10)	0.0219 (11)	−0.0084 (11)
C4	0.0680 (14)	0.0399 (11)	0.0508 (12)	0.0061 (9)	0.0193 (11)	−0.0007 (9)
C7	0.116 (3)	0.080 (2)	0.0577 (16)	0.0089 (18)	0.0318 (16)	0.0138 (15)
C5	0.0536 (12)	0.0520 (12)	0.0447 (11)	0.0054 (10)	−0.0009 (9)	−0.0071 (10)
C6	0.0383 (10)	0.0427 (11)	0.0449 (11)	−0.0004 (8)	0.0026 (8)	−0.0057 (8)
N1	0.0449 (9)	0.0390 (9)	0.0447 (9)	−0.0018 (6)	0.0129 (7)	−0.0056 (7)
C8	0.0488 (11)	0.0580 (13)	0.0418 (11)	0.0102 (9)	0.0038 (9)	−0.0003 (10)
C9	0.0537 (13)	0.0734 (16)	0.0634 (15)	−0.0154 (12)	0.0206 (11)	−0.0090 (13)
O3	0.0879 (13)	0.0678 (12)	0.0484 (10)	−0.0134 (9)	0.0284 (9)	0.0010 (8)
C10	0.0765 (15)	0.0487 (13)	0.0548 (14)	−0.0185 (11)	0.0248 (12)	−0.0147 (11)
C11	0.0856 (19)	0.080 (2)	0.0669 (18)	−0.0254 (15)	0.0062 (14)	−0.0239 (15)
O4	0.171 (3)	0.116 (2)	0.0927 (17)	−0.0743 (19)	0.0787 (18)	−0.0682 (16)

O1—S1	1.4220 (18)	C6—H6	0.9300
O2—S1	1.4291 (18)	N1—C8	1.465 (3)
S1—N1	1.6252 (17)	N1—C10	1.477 (3)
S1—C1	1.761 (2)	C8—C9	1.503 (3)
C1—C2	1.388 (3)	C8—H8A	0.9700
C1—C6	1.385 (3)	C8—H8B	0.9700
C2—C3	1.375 (4)	C9—O3	1.413 (3)
C2—H2	0.9300	C9—H9A	0.9700
C3—C4	1.392 (4)	C9—H9B	0.9700
C3—H3	0.9300	O3—H3O	0.75 (4)
C4—C5	1.385 (3)	C10—C11	1.454 (4)
C4—C7	1.504 (3)	C10—H10A	0.9700
C7—H7A	0.9600	C10—H10B	0.9700
C7—H7B	0.9600	C11—O4	1.319 (4)
C7—H7C	0.9600	C11—H11A	0.9700
C5—C6	1.382 (3)	C11—H11B	0.9700
C5—H5	0.9300	O4—H4O	0.76 (7)
O1—S1—O2	120.20 (12)	C8—N1—S1	117.52 (14)
O1—S1—N1	107.31 (11)	C10—N1—S1	116.78 (14)
O2—S1—N1	106.67 (10)	N1—C8—C9	112.75 (19)
O1—S1—C1	107.29 (10)	N1—C8—H8A	109.0
O2—S1—C1	107.90 (10)	C9—C8—H8A	109.0
N1—S1—C1	106.77 (9)	N1—C8—H8B	109.0
C2—C1—C6	120.13 (19)	C9—C8—H8B	109.0
C2—C1—S1	120.15 (17)	H8A—C8—H8B	107.8
C6—C1—S1	119.70 (15)	O3—C9—C8	109.9 (2)
C3—C2—C1	119.6 (2)	O3—C9—H9A	109.7
C3—C2—H2	120.2	C8—C9—H9A	109.7
C1—C2—H2	120.2	O3—C9—H9B	109.7
C2—C3—C4	121.3 (2)	C8—C9—H9B	109.7
C2—C3—H3	119.3	H9A—C9—H9B	108.2
C4—C3—H3	119.3	C9—O3—H3O	107 (3)
C5—C4—C3	118.0 (2)	C11—C10—N1	114.8 (2)
C5—C4—C7	120.6 (3)	C11—C10—H10A	108.6
C3—C4—C7	121.3 (2)	N1—C10—H10A	108.6
C4—C7—H7A	109.5	C11—C10—H10B	108.6
C4—C7—H7B	109.5	N1—C10—H10B	108.6
H7A—C7—H7B	109.5	H10A—C10—H10B	107.6
C4—C7—H7C	109.5	O4—C11—C10	120.6 (3)
H7A—C7—H7C	109.5	O4—C11—H11A	107.2
H7B—C7—H7C	109.5	C10—C11—H11A	107.2
C6—C5—C4	121.5 (2)	O4—C11—H11B	107.2
C6—C5—H5	119.2	C10—C11—H11B	107.2
C4—C5—H5	119.2	H11A—C11—H11B	106.8
C5—C6—C1	119.36 (19)	C10—C11—H4O	105 (2)
C5—C6—H6	120.3	H11A—C11—H4O	99.7
C1—C6—H6	120.3	H11B—C11—H4O	129.5
C8—N1—C10	117.96 (18)	C11—O4—H4O	115 (5)
O1—S1—C1—C2	−22.1 (2)	C2—C1—C6—C5	−0.7 (3)
O2—S1—C1—C2	−152.92 (17)	S1—C1—C6—C5	177.53 (16)
N1—S1—C1—C2	92.73 (18)	O1—S1—N1—C8	−159.22 (16)
O1—S1—C1—C6	159.73 (17)	O2—S1—N1—C8	−29.17 (18)
O2—S1—C1—C6	28.87 (19)	C1—S1—N1—C8	86.00 (16)
N1—S1—C1—C6	−85.47 (17)	O1—S1—N1—C10	52.0 (2)
C6—C1—C2—C3	1.2 (3)	O2—S1—N1—C10	−177.94 (17)
S1—C1—C2—C3	−177.04 (17)	C1—S1—N1—C10	−62.76 (19)
C1—C2—C3—C4	−0.4 (3)	C10—N1—C8—C9	−119.1 (2)
C2—C3—C4—C5	−0.9 (3)	S1—N1—C8—C9	92.5 (2)
C2—C3—C4—C7	179.5 (2)	N1—C8—C9—O3	63.5 (3)
C3—C4—C5—C6	1.4 (3)	C8—N1—C10—C11	94.0 (3)
C7—C4—C5—C6	−179.0 (2)	S1—N1—C10—C11	−117.4 (2)
C4—C5—C6—C1	−0.6 (3)	N1—C10—C11—O4	−54.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3	0.76 (7)	1.89 (7)	2.634 (3)	166 (7)
O3—H3O···O4i	0.75 (4)	1.92 (4)	2.661 (3)	172 (4)
C10—H10A···O1ii	0.97	2.61	3.361 (3)	135
C3—H3···Cg1iii	0.93	2.78	3.522 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O3	0.76 (7)	1.89 (7)	2.634 (3)	166 (7)
O3—H3O⋯O4i	0.75 (4)	1.92 (4)	2.661 (3)	172 (4)
C10—H10A⋯O1ii	0.97	2.61	3.361 (3)	135
C3—H3⋯Cg1iii	0.93	2.78	3.522 (2)	138

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