(2R,3S)-Methyl 2-hy­droxy-3-(4-methyl­benzene­sulfonamido)-3-phenyl­propano­ate

Fadlalla, M.I.; Friedrich, H.B.; Maguire, G.E.M.; Omondi, B.

doi:10.1107/S160053681004780X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3279-o3280

https://doi.org/10.1107/S160053681004780X

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(2R,3S)-Methyl 2-hydroxy-3-(4-methylbenzenesulfonamido)-3-phenylpropanoate

Mohamed I. Fadlalla,^a Holger B. Friedrich,^a Glenn E. M. Maguire ^a and Bernard Omondi ^b ^*

^aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa, and ^bResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, PO Box 524 Auckland Park, Johannesburg 2006, South Africa
^*Correspondence e-mail: boowaga@uj.ac.za

(Received 17 October 2010; accepted 17 November 2010; online 24 November 2010)

In the title molecule, C₁₇H₁₉NO₅S, the p-tolyl ring is oriented approximately parallel to the phenyl ring [dihedral angle = 17.2 (1)°], resulting in an intramolecular π–π interation [centroid–centroid distance = 3.184 (10) Å]. In the crystal, molecules 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_r = 349.39
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.04
wR(F²) = 0.100
S = 1.00
4016 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.65 e Å⁻³

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) x, y+1, z; (ii) -x+1, -y+1, -z+2; (iii) x, y-1, z.

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).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004780X/fl2324Isup2.hkl

checkCIF report

Comment top

Vicinal amino alcohols (beta-amino alcohol) are a common structural component in many naturally occuring and biologically active compounds. Furthermore, beta-amino alcohols are used in the synthesis of chiral ligands for asymmetric catalysis (Lohray et al., 2002, Bodkin & McLeod, 2002). As part of investigating a new synthetic route to these molecules, we report the crystal structure of the title compound (I) (Fig. 1) whose synthesis produces diastereomers which are separable using chromatography with the stable one being the one with the chirality as R at C3 and S at C4.

The molecular structure of the title compound, C₁₇H₁₉NO₅S (I), is similar to that of trans-methyl 2-hydroxy-3-(p-fluoro)phenyl-3'- (N-tosyl amino)propanoate (Zhao et al., 2005). The crystal structure is characterized by a number of intra- and inter- molecular interactions. An O-H···O and three C-H···O hydrogen bonds (Table 1) stabilize the crystal structure forming hydrogen bonded sheets that run along the b axis. In addition the p-tolyl and phenyl rings are in close proximity leading to a π–π interaction (Cg1···Cg2 = 3.8149 (10) Å) (Fig. 2). The hydrogen bonded sheets of molecules are alligned along the crystallographic ac face (Fig 3). It is worth mentioning that the H on the N atom does not contribute to a hydrogen bond as their is no acceptor in close proximity.

Related literature top

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 top

The title compound was obtained through a modified literature method (Naicker et al., 2008, Govender et al., 2003). To a nitrogen saturated Schlenk tube 6 ml of a mixture of acetonitrile and water (1:1 v/v), methyl cinnamate (0.0775 g, 0.478 mmol), chloramine-T (0.2173 g, 0.956 mmol), hydrotalcite-like catalyst (0.03 g) were added in that order. The catalyst was gravity filtered off after 24 h. The reaction mixture was then washed with sodium sulfite (1 g in 20 ml of de-ionized water) followed by 15 ml of ethyl acetate. The aqueous layer was separated from the organic layer and further washed by 3x 15 ml of ethyl acetate. The solvent of the combined organic mixture was removed in vacuo. The resulting crude product was purified by preparative high preasure liquid chromatography to yield the title compound, (I), as a white solid. Crystals of I were obtained by slow evaporation of a solution of acetonitrile and water (1:1 v/v) at room temperature (m.p. 413–418 K). Spectroscopic data: ¹H NMR (400 MHz, CDCl₃, δ. p.p.m.): = 2.3 (s, 3H), 3.3 (d, 1H), 3.7 (s, 3H), 4.3 (d, 1H), 4.8 (dd, 1H), 5.6 (d, 1H), 7.0–7.1 (m, Ar), 7.5 (m, Ar). ¹³C NMR (400 MHz, CDCl₃, δ. p.p.m.): =21.4 (s, 1 C), 53.2 (s, 1 C), 58.9 (s, 1 C), 74.2 (s, 1 C), 126.8 (s, 2 C), 126.9 (s, 2 C), 127.8 (s, 2 C), 128.4 (s, 2 C), 129.2 (s, 1 C), 137.4 (s, 1 C), 137.5 (s, 1 C), 143.1 (s, 1 C), 172.4 (s, 1 C). MS m/z-[fragment]-(%): 372.1 (M + Na⁺) calculated = 372.1 for C₁₇H₁₉NO₅SNa⁺. FT—IR (cm¹): = 3477(m), (OH), 3139(m), (NH), 2967(w), 2882(w), 1598(w), (ar), 1738(m), (C=O), 1056(m), (S=O).

Structure description top

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).

Computing details top

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).

Figures top

	Fig. 1. View of (I) (50% probability displacement ellipsoids) with H atoms presented as small spheres of arbitrary radii.
	Fig. 2. O—H···O and C—H···O hydrogen bond interactions in the crystal structure of (I). [Symmetry operators: (i) = x, 1 + y, z; (ii) = 1 - x, 1 - y, 2 - z]
	Fig. 3. Sheets of O—H···O and C—H···O hydrogen bonded molecules alligned diagonally across the ac face.

(2R,3S)-Methyl 2-hydroxy-3-(4-methylbenzenesulfonamido)-3-phenylpropanoate top

Crystal data top

C₁₇H₁₉NO₅S	F(000) = 736
M_r = 349.39	D_x = 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

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	3212 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 28.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→13
T_min = 0.971, T_max = 0.980	k = −4→7
17784 measured reflections	l = −39→39
4016 independent reflections

Refinement top

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(F_o²) + (0.0409P)² + 1.5018P] where P = (F_o² + 2F_c²)/3
4016 reflections	(Δ/σ)_max = 0.034
219 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₁₇H₁₉NO₅S	V = 1610.8 (2) Å³
M_r = 349.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4053 (8) Å	µ = 0.23 mm⁻¹
b = 5.4655 (4) Å	T = 100 K
c = 29.3768 (19) Å	0.13 × 0.11 × 0.09 mm
β = 105.386 (3)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	4016 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3212 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.980	R_int = 0.038
17784 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.04	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.00	Δρ_max = 0.67 e Å⁻³
4016 reflections	Δρ_min = −0.65 e Å⁻³
219 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+1, −y+1, −z+2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₅S
M_r	349.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.4053 (8), 5.4655 (4), 29.3768 (19)
β (°)	105.386 (3)
V (Å³)	1610.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.13 × 0.11 × 0.09

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.971, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	17784, 4016, 3212
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.04, 0.100, 1.00
No. of reflections	4016
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.65

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SAINT-Plus and XPREP (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), ORTEP-3 (Farrugia, 1999), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+1, −y+1, −z+2; (iii) x, y−1, z.

Acknowledgements

Financial assistance from the South African National Research Foundation and the University of KwaZulu-Natal is gratefully acknowledged.

References

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Volume 66| Part 12| December 2010| Pages o3279-o3280

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2R,3S)-Methyl 2-hy­dr­oxy-3-(4-methyl­benzene­sulfonamido)-3-phenyl­propano­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2R,3S)-Methyl 2-hydroxy-3-(4-methylbenzenesulfonamido)-3-phenylpropanoate