N-{(2S)-3-Hy-droxy-4-[(5-methyl-1,3,4-thia-diazol-2-yl)sulfan-yl]-1-phenyl-2-but-yl}-4-methyl-benzene-sulfonamide.

The thia-diazoyl and sulfonyl-benzene rings in the title compound, C(20)H(23)N(3)O(3)S(3), are aligned to the same side of the mol-ecule, forming a twisted 'U' shape [dihedral angle = 77.6 (5)°]. The benzyl-benzene ring is orientated in the opposite direction from the mol-ecule but projects approximately along the same axis as the other rings [dihedral angle between benzene rings = 28.2 (5)°] so that, overall, the mol-ecule has a flattened shape. The hy-droxy and amine groups are almost syn which enables the formation of inter-molecular hy-droxy-OH⋯N(thia-diazo-yl) and amine-H⋯O(sulfon-yl) hydrogen bonds leading to a supra-molecular chain aligned along the a axis.

Related literature

For background to the use of amino alcohols in medicinal chemistry, see: Ferreira et al. (2009 ▶); de Oliveira et al. (2008 ▶); Brik & Wong (2003 ▶); Ghosh et al. (2001 ▶); Parikh et al. (2005 ▶); Andrews et al. (2006 ▶). For the anti-malarial activity of hy­droxy­ethyl­piperazines, see: Cunico, Gomes, Moreth et al. (2009 ▶). For the biological activity of hy­droxy­ethyl­sulfonamides, see: Cunico et al. (2008 ▶, 2011 ▶); Cunico, Gomes, Facchinetti et al. (2009 ▶). For related structures, see: Cunico, Gomes, Harrison et al. (2009 ▶); Gomes et al. (2011 ▶).

Experimental

Crystal data

C20H23N3O3S3

M = 449.59

Orthorhombic,

a = 5.0420 (2) Å

b = 18.4840 (8) Å

c = 22.9650 (8) Å

V = 2140.25 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 120 K

0.14 × 0.02 × 0.02 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.438, T max = 1.000

12594 measured reflections

2182 independent reflections

1538 reflections with I > 2σ(I)

R int = 0.144

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.206

S = 1.29

2182 reflections

270 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: nd

Flack parameter: ?

Rogers parameter: ?

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033575/hb6366sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033575/hb6366Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033575/hb6366Isup3.cml

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

C20H23N3O3S3	F(000) = 944
Mr = 449.59	Dx = 1.395 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 20956 reflections
a = 5.0420 (2) Å	θ = 2.9–27.5°
b = 18.4840 (8) Å	µ = 0.37 mm−1
c = 22.9650 (8) Å	T = 120 K
V = 2140.25 (15) Å3	Needle, colourless
Z = 4	0.14 × 0.02 × 0.02 mm

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2182 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1538 reflections with I > 2σ(I)
graphite	Rint = 0.144
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.4°
φ & ω scans	h = −4→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −20→21
Tmin = 0.438, Tmax = 1.000	l = −27→26
12594 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)] = 0.078	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.206	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.29	(Δ/σ)max < 0.001
2182 reflections	Δρmax = 0.48 e Å−3
270 parameters	Δρmin = −0.47 e Å−3
2 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.1474 (5)	0.17021 (13)	0.05038 (10)	0.0243 (6)
S2	0.3692 (5)	0.07316 (15)	0.14153 (11)	0.0324 (7)
S3	0.2827 (4)	0.01335 (13)	−0.18450 (11)	0.0222 (6)
O1	−0.1857 (12)	0.1270 (3)	−0.0645 (3)	0.0230 (15)
H1O	−0.23 (2)	0.097 (4)	−0.039 (3)	0.034*
O2	0.1680 (13)	−0.0208 (3)	−0.2346 (3)	0.0246 (15)
O3	0.5507 (12)	0.0390 (4)	−0.1872 (3)	0.0302 (17)
N1	0.5551 (15)	0.0748 (5)	0.0380 (4)	0.027 (2)
N2	0.7075 (16)	0.0234 (4)	0.0689 (4)	0.030 (2)
N3	0.0990 (15)	0.0809 (4)	−0.1688 (3)	0.0205 (18)
H3N	−0.074 (3)	0.078 (5)	−0.173 (4)	0.025*
C1	0.3774 (19)	0.1027 (5)	0.0713 (4)	0.023 (2)
C2	0.632 (2)	0.0174 (5)	0.1215 (4)	0.029 (2)
C3	0.757 (2)	−0.0339 (6)	0.1642 (5)	0.036 (3)
H3A	0.6187	−0.0634	0.1825	0.054*
H3B	0.8512	−0.0063	0.1943	0.054*
H3C	0.8827	−0.0655	0.1438	0.054*
C4	0.215 (2)	0.1833 (5)	−0.0267 (4)	0.024 (2)
H4A	0.1495	0.2316	−0.0384	0.028*
H4B	0.4099	0.1829	−0.0326	0.028*
C5	0.0909 (18)	0.1267 (5)	−0.0661 (4)	0.019 (2)
H5	0.1553	0.0778	−0.0539	0.023*
C6	0.1811 (18)	0.1406 (5)	−0.1295 (4)	0.020 (2)
H6	0.3791	0.1436	−0.1299	0.024*
C7	0.264 (2)	−0.0480 (5)	−0.1259 (4)	0.025 (2)
C8	0.058 (2)	−0.0988 (6)	−0.1256 (5)	0.032 (3)
H8	−0.0527	−0.1045	−0.1587	0.039*
C9	0.020 (2)	−0.1406 (6)	−0.0763 (5)	0.038 (3)
H9	−0.1215	−0.1746	−0.0750	0.046*
C10	0.189 (3)	−0.1329 (6)	−0.0285 (5)	0.043 (3)
C11	0.395 (3)	−0.0845 (6)	−0.0296 (5)	0.044 (3)
H11	0.5110	−0.0797	0.0029	0.052*
C12	0.431 (2)	−0.0421 (6)	−0.0799 (5)	0.033 (3)
H12	0.5749	−0.0090	−0.0816	0.040*
C13	0.135 (4)	−0.1739 (7)	0.0276 (6)	0.073 (5)
H13A	0.2824	−0.1666	0.0546	0.110*
H13B	0.1159	−0.2255	0.0190	0.110*
H13C	−0.0296	−0.1559	0.0452	0.110*
C14	0.071 (2)	0.2108 (5)	−0.1548 (5)	0.025 (2)
H14A	−0.1230	0.2056	−0.1598	0.031*
H14B	0.1017	0.2504	−0.1265	0.031*
C15	0.190 (2)	0.2317 (5)	−0.2115 (4)	0.022 (2)
C16	0.399 (2)	0.2813 (6)	−0.2132 (5)	0.034 (3)
H16	0.4615	0.3017	−0.1777	0.041*
C17	0.519 (2)	0.3018 (6)	−0.2654 (5)	0.038 (3)
H17	0.6593	0.3359	−0.2655	0.046*
C18	0.433 (2)	0.2729 (7)	−0.3151 (6)	0.045 (3)
H18	0.5146	0.2859	−0.3509	0.054*
C19	0.227 (3)	0.2243 (6)	−0.3145 (5)	0.047 (3)
H19	0.1661	0.2042	−0.3501	0.056*
C20	0.108 (3)	0.2043 (6)	−0.2634 (5)	0.039 (3)
H20	−0.0348	0.1707	−0.2642	0.046*

	U11	U22	U33	U12	U13	U23
S1	0.0275 (13)	0.0300 (13)	0.0153 (13)	0.0022 (11)	−0.0008 (10)	−0.0003 (10)
S2	0.0342 (15)	0.0430 (16)	0.0201 (14)	0.0050 (13)	0.0017 (11)	0.0089 (11)
S3	0.0178 (12)	0.0274 (14)	0.0213 (13)	−0.0001 (10)	0.0010 (9)	−0.0063 (10)
O1	0.019 (3)	0.029 (4)	0.021 (4)	−0.005 (3)	0.002 (3)	0.006 (3)
O2	0.027 (4)	0.032 (4)	0.015 (3)	−0.010 (3)	0.000 (3)	−0.008 (3)
O3	0.017 (3)	0.045 (4)	0.029 (4)	0.002 (3)	0.001 (3)	−0.006 (3)
N1	0.014 (4)	0.044 (5)	0.022 (5)	−0.007 (4)	0.004 (3)	0.004 (4)
N2	0.027 (5)	0.035 (5)	0.028 (5)	0.009 (4)	−0.004 (4)	0.004 (4)
N3	0.017 (4)	0.026 (4)	0.018 (4)	−0.007 (3)	−0.003 (3)	−0.005 (3)
C1	0.018 (5)	0.027 (5)	0.024 (6)	−0.013 (4)	0.002 (4)	−0.003 (4)
C2	0.033 (6)	0.031 (6)	0.024 (6)	0.001 (5)	−0.008 (5)	0.003 (5)
C3	0.032 (6)	0.041 (6)	0.035 (7)	0.009 (5)	−0.002 (5)	0.007 (5)
C4	0.036 (6)	0.026 (5)	0.009 (5)	0.000 (5)	0.001 (4)	−0.003 (4)
C5	0.022 (5)	0.018 (5)	0.018 (5)	0.008 (4)	0.008 (4)	0.004 (4)
C6	0.018 (5)	0.021 (5)	0.022 (5)	0.002 (4)	0.002 (4)	−0.012 (4)
C7	0.028 (5)	0.020 (5)	0.026 (6)	0.009 (4)	0.002 (4)	−0.001 (4)
C8	0.029 (6)	0.043 (7)	0.026 (6)	0.006 (5)	−0.002 (5)	0.002 (5)
C9	0.051 (7)	0.030 (6)	0.034 (8)	0.006 (5)	−0.003 (5)	0.003 (5)
C10	0.069 (9)	0.039 (6)	0.021 (7)	0.024 (7)	−0.011 (6)	−0.004 (5)
C11	0.054 (8)	0.042 (7)	0.035 (7)	0.015 (6)	−0.021 (6)	−0.001 (5)
C12	0.038 (6)	0.032 (6)	0.029 (7)	−0.001 (5)	−0.012 (5)	−0.003 (5)
C13	0.123 (14)	0.057 (9)	0.040 (9)	0.016 (10)	0.001 (9)	0.005 (7)
C14	0.030 (6)	0.019 (5)	0.027 (6)	−0.002 (4)	0.004 (4)	−0.002 (4)
C15	0.030 (6)	0.025 (5)	0.011 (5)	0.008 (4)	−0.001 (4)	−0.004 (4)
C16	0.033 (6)	0.042 (7)	0.027 (6)	−0.010 (5)	−0.003 (5)	0.006 (5)
C17	0.040 (7)	0.036 (7)	0.038 (8)	−0.011 (5)	−0.003 (5)	0.009 (6)
C18	0.048 (7)	0.050 (8)	0.036 (8)	0.003 (6)	0.012 (6)	0.012 (6)
C19	0.089 (10)	0.041 (7)	0.010 (6)	0.002 (7)	0.007 (6)	0.001 (5)
C20	0.048 (7)	0.039 (6)	0.030 (7)	−0.009 (5)	0.001 (6)	0.009 (5)

S1—C1	1.770 (10)	C7—C8	1.397 (14)
S1—C4	1.818 (9)	C8—C9	1.384 (16)
S2—C1	1.704 (10)	C8—H8	0.9500
S2—C2	1.742 (11)	C9—C10	1.397 (16)
S3—O3	1.433 (7)	C9—H9	0.9500
S3—O2	1.435 (6)	C10—C11	1.374 (18)
S3—N3	1.596 (8)	C10—C13	1.518 (18)
S3—C7	1.763 (10)	C11—C12	1.407 (16)
O1—C5	1.395 (11)	C11—H11	0.9500
O1—H1O	0.838 (11)	C12—H12	0.9500
N1—C1	1.285 (12)	C13—H13A	0.9800
N1—N2	1.414 (11)	C13—H13B	0.9800
N2—C2	1.271 (13)	C13—H13C	0.9800
N3—C6	1.485 (11)	C14—C15	1.484 (14)
N3—H3N	0.878 (11)	C14—H14A	0.9900
C2—C3	1.504 (14)	C14—H14B	0.9900
C3—H3A	0.9800	C15—C20	1.361 (15)
C3—H3B	0.9800	C15—C16	1.398 (14)
C3—H3C	0.9800	C16—C17	1.395 (16)
C4—C5	1.520 (13)	C16—H16	0.9500
C4—H4A	0.9900	C17—C18	1.332 (17)
C4—H4B	0.9900	C17—H17	0.9500
C5—C6	1.546 (13)	C18—C19	1.374 (17)
C5—H5	1.0000	C18—H18	0.9500
C6—C14	1.526 (13)	C19—C20	1.369 (16)
C6—H6	1.0000	C19—H19	0.9500
C7—C12	1.357 (15)	C20—H20	0.9500
C1—S1—C4	103.5 (5)	C8—C7—S3	118.4 (8)
C1—S2—C2	85.4 (5)	C9—C8—C7	118.9 (11)
O3—S3—O2	119.4 (4)	C9—C8—H8	120.6
O3—S3—N3	107.4 (4)	C7—C8—H8	120.6
O2—S3—N3	107.0 (4)	C8—C9—C10	120.0 (12)
O3—S3—C7	107.3 (5)	C8—C9—H9	120.0
O2—S3—C7	107.9 (4)	C10—C9—H9	120.0
N3—S3—C7	107.4 (4)	C11—C10—C9	120.9 (11)
C5—O1—H1O	105 (8)	C11—C10—C13	118.5 (12)
C1—N1—N2	110.5 (8)	C9—C10—C13	120.4 (14)
C2—N2—N1	111.9 (8)	C10—C11—C12	118.3 (10)
C6—N3—S3	123.9 (6)	C10—C11—H11	120.8
C6—N3—H3N	112 (6)	C12—C11—H11	120.8
S3—N3—H3N	121 (6)	C7—C12—C11	121.0 (10)
N1—C1—S2	116.9 (8)	C7—C12—H12	119.5
N1—C1—S1	125.3 (8)	C11—C12—H12	119.5
S2—C1—S1	117.8 (6)	C10—C13—H13A	109.5
N2—C2—C3	123.4 (10)	C10—C13—H13B	109.5
N2—C2—S2	115.3 (7)	H13A—C13—H13B	109.5
C3—C2—S2	121.3 (8)	C10—C13—H13C	109.5
C2—C3—H3A	109.5	H13A—C13—H13C	109.5
C2—C3—H3B	109.5	H13B—C13—H13C	109.5
H3A—C3—H3B	109.5	C15—C14—C6	114.1 (8)
C2—C3—H3C	109.5	C15—C14—H14A	108.7
H3A—C3—H3C	109.5	C6—C14—H14A	108.7
H3B—C3—H3C	109.5	C15—C14—H14B	108.7
C5—C4—S1	114.2 (7)	C6—C14—H14B	108.7
C5—C4—H4A	108.7	H14A—C14—H14B	107.6
S1—C4—H4A	108.7	C20—C15—C16	116.7 (9)
C5—C4—H4B	108.7	C20—C15—C14	123.3 (9)
S1—C4—H4B	108.7	C16—C15—C14	120.0 (9)
H4A—C4—H4B	107.6	C17—C16—C15	121.9 (10)
O1—C5—C4	113.2 (8)	C17—C16—H16	119.1
O1—C5—C6	108.6 (8)	C15—C16—H16	119.1
C4—C5—C6	109.0 (7)	C18—C17—C16	119.3 (11)
O1—C5—H5	108.7	C18—C17—H17	120.4
C4—C5—H5	108.7	C16—C17—H17	120.4
C6—C5—H5	108.7	C17—C18—C19	119.8 (12)
N3—C6—C14	107.5 (8)	C17—C18—H18	120.1
N3—C6—C5	111.4 (8)	C19—C18—H18	120.1
C14—C6—C5	113.1 (7)	C20—C19—C18	121.2 (12)
N3—C6—H6	108.2	C20—C19—H19	119.4
C14—C6—H6	108.2	C18—C19—H19	119.4
C5—C6—H6	108.2	C15—C20—C19	121.1 (11)
C12—C7—C8	120.7 (10)	C15—C20—H20	119.4
C12—C7—S3	120.7 (8)	C19—C20—H20	119.4
C1—N1—N2—C2	−0.1 (12)	O3—S3—C7—C8	−158.1 (8)
O3—S3—N3—C6	−35.0 (9)	O2—S3—C7—C8	−28.3 (9)
O2—S3—N3—C6	−164.3 (7)	N3—S3—C7—C8	86.7 (8)
C7—S3—N3—C6	80.1 (8)	C12—C7—C8—C9	3.3 (15)
N2—N1—C1—S2	0.5 (10)	S3—C7—C8—C9	−171.4 (8)
N2—N1—C1—S1	179.0 (6)	C7—C8—C9—C10	−1.5 (16)
C2—S2—C1—N1	−0.6 (8)	C8—C9—C10—C11	−0.5 (18)
C2—S2—C1—S1	−179.2 (6)	C8—C9—C10—C13	174.9 (11)
C4—S1—C1—N1	3.4 (9)	C9—C10—C11—C12	0.7 (17)
C4—S1—C1—S2	−178.2 (5)	C13—C10—C11—C12	−174.8 (11)
N1—N2—C2—C3	179.3 (9)	C8—C7—C12—C11	−3.1 (16)
N1—N2—C2—S2	−0.3 (11)	S3—C7—C12—C11	171.4 (8)
C1—S2—C2—N2	0.5 (8)	C10—C11—C12—C7	1.1 (17)
C1—S2—C2—C3	−179.1 (9)	N3—C6—C14—C15	−66.3 (10)
C1—S1—C4—C5	80.3 (8)	C5—C6—C14—C15	170.2 (8)
S1—C4—C5—O1	63.4 (9)	C6—C14—C15—C20	82.7 (12)
S1—C4—C5—C6	−175.7 (6)	C6—C14—C15—C16	−96.6 (11)
S3—N3—C6—C14	141.8 (7)	C20—C15—C16—C17	−0.1 (16)
S3—N3—C6—C5	−93.7 (9)	C14—C15—C16—C17	179.2 (10)
O1—C5—C6—N3	−64.8 (9)	C15—C16—C17—C18	−0.6 (17)
C4—C5—C6—N3	171.5 (7)	C16—C17—C18—C19	0.9 (18)
O1—C5—C6—C14	56.5 (10)	C17—C18—C19—C20	−0.5 (19)
C4—C5—C6—C14	−67.3 (10)	C16—C15—C20—C19	0.5 (16)
O3—S3—C7—C12	27.3 (10)	C14—C15—C20—C19	−178.8 (11)
O2—S3—C7—C12	157.1 (8)	C18—C19—C20—C15	−0.2 (19)
N3—S3—C7—C12	−87.9 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1i	0.84 (7)	2.11 (8)	2.860 (11)	148 (8)
N3—H3N···O3i	0.88 (2)	2.05 (4)	2.902 (10)	163 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1i	0.84 (7)	2.11 (8)	2.860 (11)	148 (8)
N3—H3N⋯O3i	0.88 (2)	2.05 (4)	2.902 (10)	163 (9)

Symmetry code: (i) .