(2R,3S)-Methyl 2-hy-droxy-3-(4-methyl-benzene-sulfonamido)-3-phenyl-propano-ate.

In the title mol-ecule, C(17)H(19)NO(5)S, the p-tolyl ring is oriented approximately parallel to the phenyl ring [dihedral angle = 17.2 (1)°], resulting in an intra-molecular π-π inter-ation [centroid-centroid distance = 3.184 (10) Å]. In the crystal, mol-ecules are linked through O-H⋯O and C-H⋯O hydrogen bonds, forming hydrogen-bonded sheets lying diagonally across the ac face.

Related literature

For related structures of β-amino alcohols, see: Bergmeier (2000 ▶); Krzeminski & Wojtczak (2005 ▶). For related structures of tosyl­amino compounds, see: Coote et al. (2008 ▶); Liu et al. (2005 ▶); Chinnakali et al. (2007 ▶); Nan & Xing (2006 ▶); Fadlalla et al. (2010 ▶); Zhao et al. (2005 ▶). For the synthesis of the title compound, see: Naicker et al. (2008 ▶); Govender et al. (2003 ▶). For the use of β-amino alcohols in the synthesis of chiral ligands for asymmetric catalysis, see: Bodkin & McLeod (2002 ▶); Lohray et al. (2002 ▶).

Experimental

Crystal data

C17H19NO5S

M = 349.39

Monoclinic,

a = 10.4053 (8) Å

b = 5.4655 (4) Å

c = 29.3768 (19) Å

β = 105.386 (3)°

V = 1610.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.13 × 0.11 × 0.09 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.971, T max = 0.980

17784 measured reflections

4016 independent reflections

3212 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.04

wR(F 2) = 0.100

S = 1.00

4016 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.65 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 ▶), ORTEP-3 (Farrugia, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004780X/fl2324sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004780X/fl2324Isup2.hkl

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

C17H19NO5S	F(000) = 736
Mr = 349.39	Dx = 1.441 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18868 reflections
a = 10.4053 (8) Å	θ = 2.0–28.4°
b = 5.4655 (4) Å	µ = 0.23 mm−1
c = 29.3768 (19) Å	T = 100 K
β = 105.386 (3)°	Block, colourless
V = 1610.8 (2) Å3	0.13 × 0.11 × 0.09 mm
Z = 4

Bruker X8 APEXII 4K Kappa CCD diffractometer	3212 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→13
Tmin = 0.971, Tmax = 0.980	k = −4→7
17784 measured reflections	l = −39→39
4016 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)] = 0.04	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0409P)2 + 1.5018P] where P = (Fo2 + 2Fc2)/3
4016 reflections	(Δ/σ)max = 0.034
219 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.65 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 1480 frames were collected with a frame width of 0.5° covering upto θ = 28.41° 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. >>> The Following Model and Quality ALERTS were generated - (Acta-Mode) <<< Format: alert-number_ALERT_alert-type_alert-level text 960_ALERT_3_G Number of Intensities with I. LT. - 2*sig(I).. 1 793_ALERT_4_G The Model has Chirality at C3 (Verify) ···. R 793_ALERT_4_G The Model has Chirality at C4 (Verify) ···. S The chirality is verified and correct.

	x	y	z	Uiso*/Ueq
C1	0.60326 (17)	0.1396 (3)	1.05597 (6)	0.0179 (3)
H1A	0.6289	0.2404	1.0845	0.027*
H1B	0.6083	−0.0337	1.0648	0.027*
H1C	0.5118	0.1798	1.0383	0.027*
C2	0.70299 (16)	0.4237 (3)	1.01583 (6)	0.0151 (3)
C3	0.80464 (16)	0.4702 (3)	0.98772 (6)	0.0154 (3)
H3	0.8947	0.4182	1.0071	0.018*
C4	0.77208 (15)	0.3308 (3)	0.94058 (6)	0.0140 (3)
H4	0.7672	0.1526	0.9476	0.017*
C5	0.88195 (16)	0.3659 (3)	0.91578 (6)	0.0144 (3)
C6	0.88826 (16)	0.5749 (3)	0.88948 (6)	0.0166 (3)
H6	0.8229	0.6993	0.8868	0.02*
C7	0.98912 (17)	0.6037 (3)	0.86702 (6)	0.0203 (4)
H7	0.992	0.7462	0.8488	0.024*
C8	1.08600 (17)	0.4233 (3)	0.87122 (6)	0.0216 (4)
H8	1.1555	0.4429	0.8561	0.026*
C9	1.08063 (17)	0.2154 (3)	0.89751 (6)	0.0212 (4)
H9	1.1467	0.0921	0.9004	0.025*
C10	0.97868 (16)	0.1857 (3)	0.91979 (6)	0.0175 (3)
H10	0.9754	0.0423	0.9377	0.021*
C11	0.62837 (16)	0.3006 (3)	0.82070 (6)	0.0149 (3)
C12	0.59763 (16)	0.5127 (3)	0.79368 (6)	0.0160 (3)
H12	0.536	0.628	0.7998	0.019*
C13	0.65878 (16)	0.5527 (3)	0.75750 (6)	0.0175 (3)
H13	0.6381	0.6965	0.7388	0.021*
C14	0.74982 (17)	0.3851 (3)	0.74828 (6)	0.0188 (4)
C15	0.8146 (2)	0.4311 (4)	0.70873 (7)	0.0325 (5)
H15A	0.8962	0.3336	0.714	0.049*
H15B	0.8367	0.6052	0.708	0.049*
H15C	0.7529	0.3846	0.6786	0.049*
C16	0.77809 (17)	0.1746 (3)	0.77556 (6)	0.0201 (4)
H16	0.8393	0.0585	0.7694	0.024*
C17	0.71818 (17)	0.1312 (3)	0.81180 (6)	0.0178 (3)
H17	0.7385	−0.0131	0.8303	0.021*
N1	0.63870 (13)	0.4102 (3)	0.91306 (5)	0.0153 (3)
H1	0.6036	0.5446	0.9211	0.018*
O1	0.64240 (12)	0.5874 (2)	1.02804 (4)	0.0191 (3)
O2	0.69409 (12)	0.1881 (2)	1.02642 (4)	0.0170 (3)
O3	0.80780 (12)	0.7244 (2)	0.97843 (4)	0.0196 (3)
H3A	0.7704	0.8013	0.9961	0.029*
O4	0.57588 (13)	−0.0023 (2)	0.88103 (4)	0.0214 (3)
O5	0.42425 (12)	0.3532 (3)	0.85460 (4)	0.0235 (3)
S1	0.55584 (4)	0.25129 (8)	0.867939 (14)	0.01596 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0213 (8)	0.0183 (8)	0.0179 (8)	0.0000 (6)	0.0115 (7)	0.0030 (7)
C2	0.0173 (7)	0.0162 (8)	0.0101 (7)	−0.0019 (6)	0.0009 (6)	0.0002 (6)
C3	0.0193 (8)	0.0137 (8)	0.0133 (7)	−0.0030 (6)	0.0043 (6)	0.0013 (6)
C4	0.0158 (7)	0.0133 (8)	0.0130 (7)	−0.0006 (6)	0.0040 (6)	0.0016 (6)
C5	0.0155 (7)	0.0151 (8)	0.0124 (7)	−0.0020 (6)	0.0032 (6)	−0.0023 (6)
C6	0.0189 (8)	0.0153 (8)	0.0164 (8)	0.0017 (6)	0.0062 (6)	0.0005 (7)
C7	0.0243 (9)	0.0187 (9)	0.0203 (9)	−0.0039 (7)	0.0104 (7)	0.0005 (7)
C8	0.0176 (8)	0.0262 (10)	0.0230 (9)	−0.0031 (7)	0.0086 (7)	−0.0063 (8)
C9	0.0165 (8)	0.0225 (9)	0.0231 (9)	0.0034 (7)	0.0030 (7)	−0.0044 (7)
C10	0.0188 (8)	0.0153 (8)	0.0168 (8)	0.0005 (6)	0.0020 (6)	0.0000 (7)
C11	0.0161 (7)	0.0180 (8)	0.0114 (7)	−0.0035 (6)	0.0048 (6)	−0.0021 (6)
C12	0.0161 (7)	0.0159 (8)	0.0158 (8)	0.0016 (6)	0.0041 (6)	−0.0017 (7)
C13	0.0196 (8)	0.0166 (8)	0.0148 (8)	−0.0006 (6)	0.0019 (6)	0.0031 (7)
C14	0.0215 (8)	0.0216 (9)	0.0147 (8)	−0.0012 (7)	0.0073 (6)	0.0000 (7)
C15	0.0410 (11)	0.0362 (12)	0.0271 (10)	0.0073 (9)	0.0212 (9)	0.0076 (9)
C16	0.0223 (8)	0.0191 (9)	0.0210 (9)	0.0046 (7)	0.0096 (7)	−0.0007 (7)
C17	0.0226 (8)	0.0144 (8)	0.0166 (8)	0.0014 (6)	0.0055 (7)	0.0013 (7)
N1	0.0153 (6)	0.0183 (7)	0.0128 (6)	0.0006 (5)	0.0048 (5)	−0.0032 (6)
O1	0.0237 (6)	0.0152 (6)	0.0191 (6)	0.0006 (5)	0.0066 (5)	−0.0009 (5)
O2	0.0226 (6)	0.0144 (6)	0.0171 (6)	0.0010 (5)	0.0108 (5)	0.0032 (5)
O3	0.0314 (7)	0.0125 (6)	0.0168 (6)	−0.0041 (5)	0.0097 (5)	−0.0001 (5)
O4	0.0298 (7)	0.0189 (6)	0.0175 (6)	−0.0092 (5)	0.0101 (5)	−0.0015 (5)
O5	0.0158 (6)	0.0371 (8)	0.0180 (6)	−0.0018 (5)	0.0052 (5)	−0.0040 (6)
S1	0.01589 (19)	0.0203 (2)	0.01270 (19)	−0.00410 (15)	0.00551 (14)	−0.00200 (16)

C1—O2	1.4671 (19)	C9—H9	0.95
C1—H1A	0.98	C10—H10	0.95
C1—H1B	0.98	C11—C17	1.389 (2)
C1—H1C	0.98	C11—C12	1.393 (2)
C2—O1	1.203 (2)	C11—S1	1.7675 (16)
C2—O2	1.334 (2)	C12—C13	1.393 (2)
C2—C3	1.526 (2)	C12—H12	0.95
C3—O3	1.418 (2)	C13—C14	1.395 (2)
C3—C4	1.537 (2)	C13—H13	0.95
C3—H3	1	C14—C16	1.388 (3)
C4—N1	1.474 (2)	C14—C15	1.511 (2)
C4—C5	1.522 (2)	C15—H15A	0.98
C4—H4	1	C15—H15B	0.98
C5—C6	1.390 (2)	C15—H15C	0.98
C5—C10	1.390 (2)	C16—C17	1.390 (2)
C6—C7	1.389 (2)	C16—H16	0.95
C6—H6	0.95	C17—H17	0.95
C7—C8	1.392 (3)	N1—S1	1.6274 (14)
C7—H7	0.95	N1—H1	0.88
C8—C9	1.383 (3)	O3—H3A	0.8401
C8—H8	0.95	O4—S1	1.4387 (14)
C9—C10	1.396 (2)	O5—S1	1.4333 (13)
O2—C1—H1A	109.5	C9—C10—H10	120
O2—C1—H1B	109.5	C5—C10—H10	120
H1A—C1—H1B	109.5	C17—C11—C12	120.78 (15)
O2—C1—H1C	109.5	C17—C11—S1	119.66 (13)
H1A—C1—H1C	109.5	C12—C11—S1	119.54 (13)
H1B—C1—H1C	109.5	C13—C12—C11	118.88 (15)
O1—C2—O2	125.07 (15)	C13—C12—H12	120.6
O1—C2—C3	122.04 (15)	C11—C12—H12	120.6
O2—C2—C3	112.85 (14)	C12—C13—C14	121.06 (16)
O3—C3—C2	108.80 (13)	C12—C13—H13	119.5
O3—C3—C4	108.86 (13)	C14—C13—H13	119.5
C2—C3—C4	112.70 (13)	C16—C14—C13	118.88 (16)
O3—C3—H3	108.8	C16—C14—C15	120.84 (16)
C2—C3—H3	108.8	C13—C14—C15	120.28 (17)
C4—C3—H3	108.8	C14—C15—H15A	109.5
N1—C4—C5	114.69 (13)	C14—C15—H15B	109.5
N1—C4—C3	107.37 (13)	H15A—C15—H15B	109.5
C5—C4—C3	110.77 (13)	C14—C15—H15C	109.5
N1—C4—H4	107.9	H15A—C15—H15C	109.5
C5—C4—H4	107.9	H15B—C15—H15C	109.5
C3—C4—H4	107.9	C17—C16—C14	120.95 (16)
C6—C5—C10	119.27 (15)	C17—C16—H16	119.5
C6—C5—C4	121.45 (14)	C14—C16—H16	119.5
C10—C5—C4	119.28 (15)	C16—C17—C11	119.45 (16)
C7—C6—C5	120.67 (16)	C16—C17—H17	120.3
C7—C6—H6	119.7	C11—C17—H17	120.3
C5—C6—H6	119.7	C4—N1—S1	120.52 (11)
C6—C7—C8	119.90 (17)	C4—N1—H1	119.8
C6—C7—H7	120.1	S1—N1—H1	119.7
C8—C7—H7	120.1	C2—O2—C1	114.07 (13)
C9—C8—C7	119.72 (16)	C3—O3—H3A	109.5
C9—C8—H8	120.1	O5—S1—O4	120.52 (8)
C7—C8—H8	120.1	O5—S1—N1	106.05 (8)
C8—C9—C10	120.35 (16)	O4—S1—N1	106.78 (8)
C8—C9—H9	119.8	O5—S1—C11	107.57 (8)
C10—C9—H9	119.8	O4—S1—C11	107.16 (8)
C9—C10—C5	120.09 (16)	N1—S1—C11	108.29 (8)
O1—C2—C3—O3	−2.1 (2)	C11—C12—C13—C14	−0.3 (3)
O2—C2—C3—O3	−179.60 (13)	C12—C13—C14—C16	0.6 (3)
O1—C2—C3—C4	−122.90 (17)	C12—C13—C14—C15	179.70 (17)
O2—C2—C3—C4	59.56 (18)	C13—C14—C16—C17	−0.6 (3)
O3—C3—C4—N1	−61.99 (16)	C15—C14—C16—C17	−179.69 (18)
C2—C3—C4—N1	58.81 (17)	C14—C16—C17—C11	0.3 (3)
O3—C3—C4—C5	63.93 (17)	C12—C11—C17—C16	0.1 (3)
C2—C3—C4—C5	−175.27 (13)	S1—C11—C17—C16	−178.00 (13)
N1—C4—C5—C6	40.6 (2)	C5—C4—N1—S1	72.77 (17)
C3—C4—C5—C6	−81.10 (19)	C3—C4—N1—S1	−163.68 (11)
N1—C4—C5—C10	−139.84 (16)	O1—C2—O2—C1	−1.1 (2)
C3—C4—C5—C10	98.44 (18)	C3—C2—O2—C1	176.38 (13)
C10—C5—C6—C7	0.6 (3)	C4—N1—S1—O5	170.37 (12)
C4—C5—C6—C7	−179.90 (15)	C4—N1—S1—O4	40.68 (14)
C5—C6—C7—C8	−0.8 (3)	C4—N1—S1—C11	−74.42 (14)
C6—C7—C8—C9	0.5 (3)	C17—C11—S1—O5	−147.69 (14)
C7—C8—C9—C10	0.0 (3)	C12—C11—S1—O5	34.16 (16)
C8—C9—C10—C5	−0.2 (3)	C17—C11—S1—O4	−16.75 (16)
C6—C5—C10—C9	−0.1 (2)	C12—C11—S1—O4	165.10 (13)
C4—C5—C10—C9	−179.64 (15)	C17—C11—S1—N1	98.09 (15)
C17—C11—C12—C13	−0.1 (2)	C12—C11—S1—N1	−80.05 (14)
S1—C11—C12—C13	178.01 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2i	0.84	2.50	3.270 (2)	152
C1—H1C···O1ii	0.98	2.52	3.392 (2)	149
C4—H4···O3iii	1.00	2.50	3.484 (2)	166
C1—H1C···O1ii	0.98	2.52	3.392 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2i	0.84	2.50	3.270 (2)	152
C1—H1C⋯O1ii	0.98	2.52	3.392 (2)	149
C4—H4⋯O3iii	1.00	2.50	3.484 (2)	166
C1—H1C⋯O1ii	0.98	2.52	3.392 (2)	149

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