tert-Butyl 2-hy-droxy-3-(4-methyl-benzene-sulfonamido)-butano-ate.

In the crystal of the title compound, C(15)H(23)NO(5)S, mol-ecules are linked through N-H⋯O and O-H⋯O hydrogen-bond inter-actions, resulting in centrosymmetric dimers in which the N-H⋯O inter-actions generate R(2) (2)(12) rings and the O-H⋯O inter-actions generate R(2) (2)(14) rings. Weak inter-molecular C-H⋯O inter-actions are also observed.

Related literature

For related structures of β-amino alcohols, see: Lohray et al. (2002 ▶); Bodkin et al. (2008 ▶). For the structures of tosyl­amino compounds, see: Coote et al. (2008 ▶); Liu et al. (2005 ▶); Fadlalla et al. (2010 ▶). For the synthesis of the title compound, see: Naicker et al. (2008 ▶); Govender et al. (2003 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H23NO5S

M = 329.4

Triclinic,

a = 9.6038 (8) Å

b = 9.9059 (8) Å

c = 10.1064 (11) Å

α = 119.342 (2)°

β = 92.307 (2)°

γ = 93.422 (2)°

V = 833.95 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.22 × 0.18 × 0.14 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.954, T max = 0.970

24635 measured reflections

4192 independent reflections

3712 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.05

4192 reflections

209 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: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004934/hg2795sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004934/hg2795Isup2.hkl

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

C15H23NO5S	Z = 2
Mr = 329.4	F(000) = 352
Triclinic, P1	Dx = 1.312 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6038 (8) Å	Cell parameters from 24635 reflections
b = 9.9059 (8) Å	θ = 2.1–28.5°
c = 10.1064 (11) Å	µ = 0.22 mm−1
α = 119.342 (2)°	T = 100 K
β = 92.307 (2)°	Block, colourless
γ = 93.422 (2)°	0.22 × 0.18 × 0.14 mm
V = 833.95 (13) Å3

Bruker X8 APEXII 4K Kappa CCD diffractometer	3712 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.954, Tmax = 0.970	k = −13→13
24635 measured reflections	l = −13→13
4192 independent 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0395P)2 + 0.3237P] where P = (Fo2 + 2Fc2)/3
4192 reflections	(Δ/σ)max = 0.005
209 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. The intensity data was collected on a Bruker X8 Apex 4 K CCD diffractometer using an exposure time of 15 sec/per frame. A total of 3328 frames were collected with a frame width of 0.5° covering upto θ = 28.45° with 99.8% completeness accomplished.

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
C1	0.74584 (13)	1.08296 (13)	0.93414 (13)	0.0208 (2)
H1A	0.6562	1.118	0.9193	0.031*
H1B	0.8195	1.1223	0.8942	0.031*
H1C	0.7685	1.1225	1.0431	0.031*
C2	0.87462 (12)	0.84588 (14)	0.86348 (14)	0.0241 (2)
H2A	0.9444	0.8772	0.8132	0.036*
H2B	0.8629	0.7322	0.8145	0.036*
H2C	0.9061	0.8896	0.9712	0.036*
C3	0.61532 (13)	0.83957 (14)	0.90149 (13)	0.0222 (2)
H3A	0.6156	0.7262	0.8517	0.033*
H3B	0.5263	0.8661	0.8736	0.033*
H3C	0.627	0.8836	1.0122	0.033*
C4	0.73538 (11)	0.90605 (13)	0.85019 (12)	0.0165 (2)
C5	0.68030 (10)	0.71782 (12)	0.58068 (12)	0.0145 (2)
C6	0.63194 (11)	0.69956 (12)	0.42678 (12)	0.0151 (2)
H6	0.7064	0.7491	0.3939	0.018*
C7	0.49600 (11)	0.77696 (12)	0.43670 (12)	0.0152 (2)
H7	0.5149	0.891	0.5094	0.018*
C8	0.44465 (12)	0.75423 (15)	0.28179 (13)	0.0223 (2)
H8A	0.3603	0.8085	0.2919	0.033*
H8B	0.4228	0.643	0.2101	0.033*
H8C	0.5178	0.7965	0.2438	0.033*
C9	0.12195 (11)	0.73713 (13)	0.43575 (12)	0.0166 (2)
C10	0.05152 (11)	0.58888 (13)	0.37062 (13)	0.0177 (2)
H10	0.0739	0.5198	0.4067	0.021*
C11	−0.05154 (11)	0.54303 (14)	0.25272 (13)	0.0197 (2)
H11	−0.0984	0.4414	0.2071	0.024*
C12	−0.08741 (11)	0.64442 (15)	0.19995 (13)	0.0209 (2)
C13	−0.01768 (12)	0.79315 (15)	0.26927 (14)	0.0233 (2)
H13	−0.0425	0.8639	0.2362	0.028*
C14	0.08753 (12)	0.84021 (14)	0.38584 (14)	0.0215 (2)
H14	0.1352	0.9413	0.4308	0.026*
C15	−0.19933 (13)	0.59239 (18)	0.07100 (15)	0.0296 (3)
H15A	−0.1592	0.5302	−0.0263	0.044*
H15B	−0.2358	0.6838	0.0733	0.044*
H15C	−0.2756	0.5295	0.0824	0.044*
N1	0.39695 (9)	0.71013 (11)	0.50168 (10)	0.01484 (18)
O1	0.70108 (8)	0.86607 (8)	0.68847 (8)	0.01528 (15)
O2	0.69788 (8)	0.60683 (9)	0.59739 (9)	0.01913 (17)
O3	0.60741 (8)	0.53975 (9)	0.31707 (9)	0.01922 (17)
H3	0.6564	0.4879	0.3431	0.029*
O4	0.21687 (9)	0.71817 (10)	0.66814 (9)	0.02355 (18)
O5	0.29082 (9)	0.95624 (10)	0.65376 (10)	0.02641 (19)
S1	0.25877 (3)	0.79036 (3)	0.58022 (3)	0.01691 (8)
H1D	0.3859 (16)	0.6124 (18)	0.4581 (17)	0.025 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0283 (6)	0.0164 (5)	0.0150 (5)	−0.0004 (4)	−0.0005 (4)	0.0059 (4)
C2	0.0216 (5)	0.0238 (6)	0.0233 (6)	0.0015 (4)	−0.0067 (4)	0.0095 (5)
C3	0.0261 (6)	0.0222 (5)	0.0196 (5)	0.0003 (4)	0.0039 (4)	0.0114 (5)
C4	0.0196 (5)	0.0169 (5)	0.0124 (5)	0.0001 (4)	−0.0021 (4)	0.0072 (4)
C5	0.0108 (4)	0.0148 (5)	0.0162 (5)	0.0007 (4)	0.0006 (4)	0.0065 (4)
C6	0.0152 (5)	0.0141 (5)	0.0140 (5)	0.0003 (4)	0.0008 (4)	0.0055 (4)
C7	0.0159 (5)	0.0144 (5)	0.0160 (5)	0.0000 (4)	−0.0002 (4)	0.0083 (4)
C8	0.0221 (5)	0.0290 (6)	0.0201 (5)	0.0010 (4)	−0.0021 (4)	0.0159 (5)
C9	0.0138 (5)	0.0186 (5)	0.0178 (5)	0.0042 (4)	0.0029 (4)	0.0088 (4)
C10	0.0153 (5)	0.0201 (5)	0.0206 (5)	0.0044 (4)	0.0031 (4)	0.0119 (4)
C11	0.0152 (5)	0.0230 (5)	0.0211 (5)	0.0016 (4)	0.0018 (4)	0.0112 (5)
C12	0.0135 (5)	0.0337 (6)	0.0211 (5)	0.0060 (4)	0.0051 (4)	0.0171 (5)
C13	0.0196 (5)	0.0310 (6)	0.0306 (6)	0.0089 (5)	0.0064 (5)	0.0229 (5)
C14	0.0192 (5)	0.0197 (5)	0.0287 (6)	0.0046 (4)	0.0042 (4)	0.0140 (5)
C15	0.0204 (6)	0.0507 (8)	0.0263 (6)	0.0044 (5)	0.0003 (5)	0.0256 (6)
N1	0.0145 (4)	0.0121 (4)	0.0174 (4)	0.0014 (3)	0.0016 (3)	0.0068 (4)
O1	0.0187 (4)	0.0130 (3)	0.0129 (3)	0.0001 (3)	−0.0015 (3)	0.0058 (3)
O2	0.0199 (4)	0.0148 (4)	0.0221 (4)	0.0016 (3)	−0.0027 (3)	0.0090 (3)
O3	0.0220 (4)	0.0143 (4)	0.0157 (4)	0.0026 (3)	−0.0009 (3)	0.0031 (3)
O4	0.0227 (4)	0.0316 (5)	0.0163 (4)	0.0011 (3)	0.0028 (3)	0.0118 (4)
O5	0.0257 (4)	0.0159 (4)	0.0268 (4)	0.0034 (3)	0.0006 (3)	0.0022 (3)
S1	0.01644 (13)	0.01627 (13)	0.01483 (13)	0.00257 (9)	0.00163 (9)	0.00506 (10)

C1—C4	1.5218 (15)	C8—H8B	0.98
C1—H1A	0.98	C8—H8C	0.98
C1—H1B	0.98	C9—C14	1.3921 (15)
C1—H1C	0.98	C9—C10	1.3949 (15)
C2—C4	1.5235 (15)	C9—S1	1.7733 (11)
C2—H2A	0.98	C10—C11	1.3881 (15)
C2—H2B	0.98	C10—H10	0.95
C2—H2C	0.98	C11—C12	1.4012 (16)
C3—C4	1.5245 (16)	C11—H11	0.95
C3—H3A	0.98	C12—C13	1.3938 (18)
C3—H3B	0.98	C12—C15	1.5106 (16)
C3—H3C	0.98	C13—C14	1.3914 (17)
C4—O1	1.4978 (12)	C13—H13	0.95
C5—O2	1.2115 (13)	C14—H14	0.95
C5—O1	1.3277 (12)	C15—H15A	0.98
C5—C6	1.5244 (14)	C15—H15B	0.98
C6—O3	1.4161 (12)	C15—H15C	0.98
C6—C7	1.5353 (14)	N1—S1	1.6172 (9)
C6—H6	1	N1—H1D	0.842 (16)
C7—N1	1.4750 (13)	O3—H3	0.84
C7—C8	1.5245 (15)	O4—S1	1.4422 (9)
C7—H7	1	O5—S1	1.4393 (9)
C8—H8A	0.98
C4—C1—H1A	109.5	C7—C8—H8B	109.5
C4—C1—H1B	109.5	H8A—C8—H8B	109.5
H1A—C1—H1B	109.5	C7—C8—H8C	109.5
C4—C1—H1C	109.5	H8A—C8—H8C	109.5
H1A—C1—H1C	109.5	H8B—C8—H8C	109.5
H1B—C1—H1C	109.5	C14—C9—C10	120.57 (10)
C4—C2—H2A	109.5	C14—C9—S1	120.59 (9)
C4—C2—H2B	109.5	C10—C9—S1	118.82 (8)
H2A—C2—H2B	109.5	C11—C10—C9	119.49 (10)
C4—C2—H2C	109.5	C11—C10—H10	120.3
H2A—C2—H2C	109.5	C9—C10—H10	120.3
H2B—C2—H2C	109.5	C10—C11—C12	120.95 (11)
C4—C3—H3A	109.5	C10—C11—H11	119.5
C4—C3—H3B	109.5	C12—C11—H11	119.5
H3A—C3—H3B	109.5	C13—C12—C11	118.43 (10)
C4—C3—H3C	109.5	C13—C12—C15	121.30 (11)
H3A—C3—H3C	109.5	C11—C12—C15	120.27 (11)
H3B—C3—H3C	109.5	C14—C13—C12	121.41 (10)
O1—C4—C1	102.44 (8)	C14—C13—H13	119.3
O1—C4—C2	109.60 (9)	C12—C13—H13	119.3
C1—C4—C2	111.41 (9)	C13—C14—C9	119.13 (11)
O1—C4—C3	108.99 (9)	C13—C14—H14	120.4
C1—C4—C3	111.22 (9)	C9—C14—H14	120.4
C2—C4—C3	112.66 (10)	C12—C15—H15A	109.5
O2—C5—O1	125.85 (10)	C12—C15—H15B	109.5
O2—C5—C6	122.05 (9)	H15A—C15—H15B	109.5
O1—C5—C6	112.09 (9)	C12—C15—H15C	109.5
O3—C6—C5	109.87 (8)	H15A—C15—H15C	109.5
O3—C6—C7	108.58 (8)	H15B—C15—H15C	109.5
C5—C6—C7	110.83 (8)	C7—N1—S1	123.52 (7)
O3—C6—H6	109.2	C7—N1—H1D	116.2 (10)
C5—C6—H6	109.2	S1—N1—H1D	112.5 (10)
C7—C6—H6	109.2	C5—O1—C4	119.50 (8)
N1—C7—C8	114.28 (9)	C6—O3—H3	109.5
N1—C7—C6	105.79 (8)	O5—S1—O4	120.06 (5)
C8—C7—C6	110.98 (9)	O5—S1—N1	107.61 (5)
N1—C7—H7	108.5	O4—S1—N1	105.57 (5)
C8—C7—H7	108.5	O5—S1—C9	108.09 (5)
C6—C7—H7	108.5	O4—S1—C9	106.33 (5)
C7—C8—H8A	109.5	N1—S1—C9	108.80 (5)
O2—C5—C6—O3	2.43 (14)	S1—C9—C14—C13	178.17 (9)
O1—C5—C6—O3	−178.31 (8)	C8—C7—N1—S1	−76.81 (11)
O2—C5—C6—C7	122.43 (11)	C6—C7—N1—S1	160.79 (7)
O1—C5—C6—C7	−58.31 (11)	O2—C5—O1—C4	−6.69 (15)
O3—C6—C7—N1	67.16 (10)	C6—C5—O1—C4	174.08 (8)
C5—C6—C7—N1	−53.61 (11)	C1—C4—O1—C5	−178.29 (9)
O3—C6—C7—C8	−57.32 (11)	C2—C4—O1—C5	63.33 (12)
C5—C6—C7—C8	−178.09 (9)	C3—C4—O1—C5	−60.39 (12)
C14—C9—C10—C11	1.46 (16)	C7—N1—S1—O5	−33.34 (10)
S1—C9—C10—C11	−177.12 (8)	C7—N1—S1—O4	−162.69 (8)
C9—C10—C11—C12	−1.07 (17)	C7—N1—S1—C9	83.54 (9)
C10—C11—C12—C13	−0.37 (17)	C14—C9—S1—O5	15.26 (11)
C10—C11—C12—C15	179.70 (10)	C10—C9—S1—O5	−166.16 (9)
C11—C12—C13—C14	1.47 (17)	C14—C9—S1—O4	145.40 (9)
C15—C12—C13—C14	−178.60 (11)	C10—C9—S1—O4	−36.01 (10)
C12—C13—C14—C9	−1.10 (18)	C14—C9—S1—N1	−101.32 (10)
C10—C9—C14—C13	−0.39 (17)	C10—C9—S1—N1	77.26 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O2i	0.842 (16)	2.059 (16)	2.8625 (12)	159.5 (14)
O3—H3···O4i	0.84	2.40	3.2041 (12)	162
C1—H1C···O4ii	0.98	2.54	3.4936 (14)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O2i	0.842 (16)	2.059 (16)	2.8625 (12)	159.5 (14)
O3—H3⋯O4i	0.84	2.40	3.2041 (12)	162
C1—H1C⋯O4ii	0.98	2.54	3.4936 (14)	164

Symmetry codes: (i) ; (ii) .