(±)-N-(3-Hydr­oxy-1,2-diphenyl­prop­yl)-4-methyl­benzene­sulfonamide

Tong, S.T.; Barker, D.; Choi, K.W.; Boyd, P.D.W.; Brimble, M.A.

doi:10.1107/S1600536808028948

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1990

doi:10.1107/S1600536808028948

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(±)-N-(3-Hydroxy-1,2-diphenylpropyl)-4-methylbenzenesulfonamide

Sok Teng Tong,^a David Barker,^a ^* Ka Wai Choi,^a Peter D. W. Boyd ^a and Margaret A. Brimble ^a

^aDepartment of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand
^*Correspondence e-mail: d.barker@auckland.ac.nz

(Received 29 July 2008; accepted 10 September 2008; online 24 September 2008)

In the title compound, C₂₂H₂₃NO₃S, the relative stereochemistry of the two stereogenic centres is anti with respect to the H atoms. The molecular packing of the crystal shows a double-strand arrangement, consisting of one strand of (S*,S*) enantiomers and one strand of (R*,R*) enantiomers. Both strands lie parallel to each other along the a axis. Each strand is made up of dimers in which the molecules are connected to each other via an intermolecular O—H⋯O hydrogen bond between the hydroxyl groups and an O—H⋯π interaction with the aromatic ring. These units are then connected to neighbouring dimers via N—H⋯O hydrogen bonds and C—H⋯O interactions. Intramolecular C—H⋯O interactions are also observed.

Related literature

For a similar organocatalytic α-oxdiation of ketones, see: Engqvist et al. (2005 ). For a related structure, see: Chinnakali et al. (2007 ).

Experimental

Crystal data

C₂₂H₂₃NO₃S
M_r = 381.47
Monoclinic, C 2/c
a = 39.4702 (16) Å
b = 5.4270 (2) Å
c = 17.4287 (7) Å
β = 91.028 (2)°
V = 3732.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 90 (2) K
0.4 × 0.16 × 0.14 mm

Data collection

Bruker SMART diffractometer with APEXII CCD detector
Absorption correction: none
22582 measured reflections
4478 independent reflections
3763 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.193
S = 1.13
4478 reflections
245 parameters
15 restraints
H-atom parameters constrained
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.45	3.122 (3)	136
O3—H3A⋯O3ⁱⁱ	0.85	2.06	2.910 (5)	180
C4—H4⋯O1	0.93	2.55	2.909 (4)	104
C8—H8⋯O1	0.98	2.61	2.958 (3)	101
C1—H1A⋯O2ⁱⁱⁱ	0.96	2.63	3.557 (4)	161
C1—H1B⋯O2^iv	0.96	2.74	3.552 (4)	142
O3—H3B⋯C16ⁱⁱ	0.86	2.67	3.489 (4)	160.1
O3—H3B⋯C17ⁱⁱ	0.86	2.85	3.499 (4)	133.7
Symmetry codes: (i) x, y+1, z; (ii) $[-x, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1995 ); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028948/pv2094sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028948/pv2094Isup2.hkl

checkCIF report

Comment top

The title racemic sulfonamide was obtained unintentionally as a product from the study of the organocatalytic α-oxidation of phenylacetaldehyde catalysed by (S)-proline. The relative stereochemistry of the two stereogenic centres was established by X-ray crystallography as anti with respect to the H atoms of C8 and C15 (Fig. 1).

The molecular packing of the crystal shows a double strand arrangement, which consists of one strand of (8S*,15S*) enantiomers and one strand of (8R*,15R*) enantiomers. Both strands lie parallel to each other along the a axis and a number of hydrogen bonds has been observed throughtout the crystal lattice.

Each strand is made up of homodimeric units in which the sulfonamide molecules are connected to each other by intermolecular hydrogen bonds between the hydroxyl groups (O3—H3···O3) as well as the O—H···π interaction with the aromatic ring. The dimer is, in turn, linked to the next dimer along the strand via non-conventional hydrogen bonds (C1—H1A···O2—S1 and C1—H1B···O2—S1). Finally, neighbouring strand of the same stereochemistry are connected to each other via conventional (N1—H1···O1—S1) and non-conventional (C1—H1A···O2—S1 and C1—H1B···O2—S1) hydrogen bonds (Fig. 2).

Non-conventional intramolecular hydrogen interactions (C4—H4···O1—S1 and C8—H8···O1—S1) are also observed with a distance of 2.55 and 2.61 Å between the hydrogen and the acceptor oxygen (Table 1).

Related literature top

For similar organocatalytic α-oxdiation of ketones, see: Engqvist et al. (2005). For a related structure, see: Chinnakali et al. (2007).

Experimental top

To a solution of 3-phenyl-2-tosyl-1,2-oxaziridine (551 mg, 2.00 mmol) in distilled THF (8 ml) was added under ambient atmosphere (S)-proline (69.1 mg, 0.600 mmol). After 5 minutes, phenylacetaldehyde (0.450 ml, 4.00 mmol) was added. After 1 h, sodium borohydride (151 mg, 4.00 mmol) was added to the mixture at 273 K and the mixture was stirred overnight. The mixture was then poured onto a biphasic mixture of HCl (1 mol l^-1) and EtOAc (1:1, 8 ml) at 273 K and vigorously stirred for 10 minutes. The organic phase was separated and the aqueous phase was extracted with EtOAc (8 ml x 4). The combined organic extracts were washed with brine, dried over MgSO₄ and concentrated in vacuo to afford a yellow oil. Purification by flash chromatography using hexane–EtOAc (2:1 to 1:1) as eluent yielded the title sulfonamide as a white solid (6%). Recrystallization of the title sulfonamide in hexane–CH₂Cl₂ (4:1) afforded colourless needles.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2008).

Figures top

Fig. 1. The molecular structure and atom numbering scheme of the title compound with displacement ellipsoids drawn at the 50% probability level for non-H atoms.

Fig. 2. The unit cell packing of the title compound showing double strands of (8S*,15S*) and (8R*,15R*) enantiomers. A third strand of (8S*,15S*) sulfonamide (dimmed) which is positioned below the unit cell is also depicted in the figure to show the hydrogen bondings between the strands. Dashed lines represent hydrogen bonds; hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

(±)-N-(3-hydroxy-1,2-diphenylpropyl)-4-methylbenzenesulfonamide top

Crystal data top

C₂₂H₂₃NO₃S	D_x = 1.358 Mg m⁻³
M_r = 381.47	Melting point: 426.7(8) K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 39.4702 (16) Å	Cell parameters from 6191 reflections
b = 5.4270 (2) Å	θ = 1.0–28.0°
c = 17.4287 (7) Å	µ = 0.20 mm⁻¹
β = 91.028 (2)°	T = 90 K
V = 3732.7 (3) Å³	Needle, colourless
Z = 8	0.4 × 0.16 × 0.14 mm
F(000) = 1616

Data collection top

Bruker SMART diffractometer with APEXII CCD detector	3763 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 28.0°, θ_min = 1.0°
ω scans	h = −51→51
22582 measured reflections	k = −7→7
4478 independent reflections	l = −22→22

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.193	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0794P)² + 19.2449P] where P = (F_o² + 2F_c²)/3
4478 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 1.06 e Å⁻³
15 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₂₂H₂₃NO₃S	V = 3732.7 (3) Å³
M_r = 381.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 39.4702 (16) Å	µ = 0.20 mm⁻¹
b = 5.4270 (2) Å	T = 90 K
c = 17.4287 (7) Å	0.4 × 0.16 × 0.14 mm
β = 91.028 (2)°

Data collection top

Bruker SMART diffractometer with APEXII CCD detector	3763 reflections with I > 2σ(I)
22582 measured reflections	R_int = 0.042
4478 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	15 restraints
wR(F²) = 0.193	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0794P)² + 19.2449P] where P = (F_o² + 2F_c²)/3
4478 reflections	Δρ_max = 1.06 e Å⁻³
245 parameters	Δρ_min = −0.64 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.158723 (16)	0.06828 (12)	0.28375 (4)	0.01431 (19)
O1	0.14448 (5)	−0.1745 (4)	0.27404 (12)	0.0186 (4)
O2	0.17401 (5)	0.1376 (4)	0.35572 (11)	0.0209 (5)
O3	0.02222 (6)	0.6152 (6)	0.18428 (13)	0.0382 (7)
H3A	0.0092	0.6156	0.2229	0.057*	0.50
H3B	0.0008	0.5906	0.1799	0.057*	0.50
N1	0.12844 (6)	0.2624 (4)	0.26835 (13)	0.0150 (5)
H1	0.1283	0.3959	0.2949	0.018*
C5	0.19060 (7)	0.1017 (5)	0.21504 (15)	0.0138 (5)
C15	0.07339 (7)	0.4164 (5)	0.23044 (15)	0.0154 (5)
H15	0.0843	0.5788	0.2313	0.019*
C6	0.21262 (7)	0.3020 (5)	0.22046 (16)	0.0178 (6)
H6	0.2090	0.4253	0.2564	0.021*
C21	0.06575 (7)	0.5353 (6)	0.36894 (17)	0.0185 (6)
H21	0.0786	0.6753	0.3597	0.022*
C2	0.24609 (7)	0.1333 (5)	0.11774 (16)	0.0170 (5)
C16	0.05938 (6)	0.3698 (5)	0.30955 (15)	0.0150 (5)
C10	0.10495 (7)	0.0475 (5)	0.07735 (16)	0.0182 (6)
H10	0.0919	−0.0855	0.0928	0.022*
C22	0.04555 (7)	0.4221 (6)	0.16845 (16)	0.0231 (6)
H22A	0.0555	0.4487	0.1187	0.028*
H22B	0.0338	0.2653	0.1672	0.028*
C17	0.04036 (7)	0.1590 (5)	0.32496 (17)	0.0194 (6)
H17	0.0361	0.0451	0.2861	0.023*
C14	0.13191 (7)	0.4350 (5)	0.10406 (16)	0.0176 (6)
H14	0.1369	0.5635	0.1377	0.021*
C8	0.10096 (6)	0.2233 (5)	0.21110 (14)	0.0133 (5)
H8	0.0914	0.0591	0.2196	0.016*
C9	0.11285 (6)	0.2352 (5)	0.12954 (15)	0.0142 (5)
C13	0.14347 (7)	0.4453 (6)	0.02985 (17)	0.0200 (6)
H13	0.1563	0.5791	0.0141	0.024*
C3	0.22313 (8)	−0.0595 (6)	0.11139 (18)	0.0235 (6)
H3	0.2263	−0.1793	0.0740	0.028*
C4	0.19557 (7)	−0.0777 (6)	0.15959 (18)	0.0213 (6)
H4	0.1806	−0.2092	0.1547	0.026*
C11	0.11646 (8)	0.0577 (6)	0.00254 (17)	0.0221 (6)
H11	0.1111	−0.0685	−0.0316	0.027*
C19	0.03415 (8)	0.2868 (6)	0.45638 (17)	0.0235 (6)
H19	0.0257	0.2601	0.5051	0.028*
C7	0.24002 (7)	0.3160 (6)	0.17183 (16)	0.0193 (6)
H7	0.2546	0.4502	0.1755	0.023*
C12	0.13588 (7)	0.2554 (6)	−0.02141 (16)	0.0205 (6)
H12	0.1438	0.2611	−0.0713	0.025*
C20	0.05321 (8)	0.4953 (6)	0.44183 (17)	0.0230 (6)
H20	0.0576	0.6085	0.4808	0.028*
C18	0.02775 (7)	0.1177 (6)	0.39810 (18)	0.0222 (6)
H18	0.0151	−0.0229	0.4078	0.027*
C1	0.27747 (7)	0.1382 (6)	0.06967 (18)	0.0231 (6)
H1A	0.2945	0.0338	0.0926	0.035*
H1B	0.2859	0.3039	0.0669	0.035*
H1C	0.2720	0.0801	0.0189	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0145 (3)	0.0139 (3)	0.0144 (3)	0.0006 (2)	−0.0002 (2)	0.0022 (2)
O1	0.0180 (9)	0.0144 (10)	0.0235 (10)	−0.0022 (8)	0.0015 (7)	0.0024 (8)
O2	0.0228 (10)	0.0240 (11)	0.0157 (10)	−0.0013 (8)	−0.0030 (7)	0.0036 (8)
O3	0.0277 (12)	0.0627 (18)	0.0240 (12)	0.0281 (13)	−0.0033 (9)	−0.0032 (12)
N1	0.0165 (11)	0.0146 (11)	0.0137 (10)	0.0022 (9)	−0.0020 (8)	−0.0027 (9)
C5	0.0145 (12)	0.0117 (12)	0.0152 (12)	0.0015 (10)	−0.0017 (9)	0.0012 (10)
C15	0.0172 (12)	0.0137 (13)	0.0154 (12)	0.0023 (10)	0.0018 (9)	0.0000 (10)
C6	0.0231 (13)	0.0142 (13)	0.0162 (12)	−0.0019 (11)	−0.0006 (10)	−0.0021 (10)
C21	0.0176 (13)	0.0172 (14)	0.0206 (14)	−0.0016 (11)	−0.0003 (10)	0.0011 (11)
C2	0.0156 (12)	0.0180 (14)	0.0174 (13)	0.0015 (10)	−0.0015 (9)	0.0038 (11)
C16	0.0131 (11)	0.0150 (13)	0.0169 (13)	0.0033 (10)	0.0014 (9)	0.0014 (10)
C10	0.0206 (13)	0.0148 (13)	0.0191 (13)	−0.0010 (11)	−0.0010 (10)	−0.0024 (11)
C22	0.0188 (13)	0.0355 (18)	0.0152 (13)	0.0079 (12)	0.0006 (10)	−0.0009 (12)
C17	0.0209 (13)	0.0151 (14)	0.0221 (14)	0.0009 (11)	0.0003 (10)	−0.0006 (11)
C14	0.0187 (13)	0.0177 (14)	0.0165 (13)	−0.0011 (11)	0.0005 (10)	−0.0034 (11)
C8	0.0151 (12)	0.0125 (12)	0.0123 (12)	0.0001 (10)	−0.0006 (9)	−0.0012 (10)
C9	0.0124 (11)	0.0144 (13)	0.0158 (12)	0.0021 (10)	−0.0009 (9)	−0.0016 (10)
C13	0.0189 (13)	0.0205 (14)	0.0206 (14)	−0.0010 (11)	0.0034 (10)	0.0003 (11)
C3	0.0268 (15)	0.0190 (15)	0.0251 (15)	−0.0022 (12)	0.0069 (12)	−0.0067 (12)
C4	0.0208 (14)	0.0169 (14)	0.0262 (15)	−0.0059 (11)	0.0034 (11)	−0.0064 (12)
C11	0.0285 (15)	0.0198 (15)	0.0180 (14)	0.0032 (12)	−0.0019 (11)	−0.0074 (11)
C19	0.0239 (14)	0.0286 (17)	0.0183 (13)	0.0051 (12)	0.0063 (11)	0.0065 (12)
C7	0.0195 (13)	0.0168 (14)	0.0213 (14)	−0.0057 (11)	−0.0016 (10)	0.0013 (11)
C12	0.0200 (13)	0.0288 (16)	0.0129 (12)	0.0047 (12)	0.0029 (10)	−0.0011 (11)
C20	0.0304 (16)	0.0231 (15)	0.0155 (13)	0.0014 (12)	0.0008 (11)	−0.0009 (12)
C18	0.0197 (14)	0.0179 (14)	0.0291 (15)	0.0008 (11)	0.0037 (11)	0.0065 (12)
C1	0.0191 (13)	0.0259 (16)	0.0245 (15)	0.0008 (12)	0.0032 (11)	0.0053 (13)

Geometric parameters (Å, º) top

S1—O2	1.432 (2)	C22—H22A	0.9700
S1—O1	1.441 (2)	C22—H22B	0.9700
S1—N1	1.612 (2)	C17—C18	1.395 (4)
S1—C5	1.762 (3)	C17—H17	0.9300
O3—C22	1.425 (4)	C14—C13	1.381 (4)
O3—H3A	0.8541	C14—C9	1.397 (4)
O3—H3B	0.8579	C14—H14	0.9300
N1—C8	1.476 (3)	C8—C9	1.506 (3)
N1—H1	0.8600	C8—H8	0.9800
C5—C4	1.389 (4)	C13—C12	1.393 (4)
C5—C6	1.394 (4)	C13—H13	0.9300
C15—C16	1.516 (4)	C3—C4	1.390 (4)
C15—C22	1.528 (4)	C3—H3	0.9300
C15—C8	1.552 (4)	C4—H4	0.9300
C15—H15	0.9800	C11—C12	1.387 (4)
C6—C7	1.388 (4)	C11—H11	0.9300
C6—H6	0.9300	C19—C20	1.384 (5)
C21—C20	1.389 (4)	C19—C18	1.389 (5)
C21—C16	1.390 (4)	C19—H19	0.9300
C21—H21	0.9300	C7—H7	0.9300
C2—C3	1.387 (4)	C12—H12	0.9300
C2—C7	1.392 (4)	C20—H20	0.9300
C2—C1	1.508 (4)	C18—H18	0.9300
C16—C17	1.397 (4)	C1—H1A	0.9600
C10—C11	1.389 (4)	C1—H1B	0.9600
C10—C9	1.397 (4)	C1—H1C	0.9600
C10—H10	0.9300

O2—S1—O1	120.01 (13)	C13—C14—C9	121.2 (3)
O2—S1—N1	105.87 (13)	C13—C14—H14	119.4
O1—S1—N1	106.94 (12)	C9—C14—H14	119.4
O2—S1—C5	105.87 (12)	N1—C8—C9	113.2 (2)
O1—S1—C5	107.24 (12)	N1—C8—C15	105.4 (2)
N1—S1—C5	110.85 (12)	C9—C8—C15	114.1 (2)
C22—O3—H3A	123.7	N1—C8—H8	108.0
C22—O3—H3B	120.5	C9—C8—H8	108.0
H3A—O3—H3B	57.6	C15—C8—H8	108.0
C8—N1—S1	123.52 (19)	C14—C9—C10	118.3 (3)
C8—N1—H1	118.2	C14—C9—C8	120.8 (2)
S1—N1—H1	118.2	C10—C9—C8	120.9 (2)
C4—C5—C6	119.9 (3)	C14—C13—C12	120.0 (3)
C4—C5—S1	120.8 (2)	C14—C13—H13	120.0
C6—C5—S1	119.1 (2)	C12—C13—H13	120.0
C16—C15—C22	112.2 (2)	C2—C3—C4	121.5 (3)
C16—C15—C8	110.7 (2)	C2—C3—H3	119.2
C22—C15—C8	111.0 (2)	C4—C3—H3	119.2
C16—C15—H15	107.6	C5—C4—C3	119.5 (3)
C22—C15—H15	107.6	C5—C4—H4	120.2
C8—C15—H15	107.6	C3—C4—H4	120.2
C7—C6—C5	119.6 (3)	C12—C11—C10	120.3 (3)
C7—C6—H6	120.2	C12—C11—H11	119.8
C5—C6—H6	120.2	C10—C11—H11	119.8
C20—C21—C16	121.2 (3)	C20—C19—C18	119.9 (3)
C20—C21—H21	119.4	C20—C19—H19	120.1
C16—C21—H21	119.4	C18—C19—H19	120.1
C3—C2—C7	118.1 (3)	C6—C7—C2	121.3 (3)
C3—C2—C1	120.7 (3)	C6—C7—H7	119.3
C7—C2—C1	121.1 (3)	C2—C7—H7	119.3
C21—C16—C17	118.5 (3)	C11—C12—C13	119.5 (3)
C21—C16—C15	120.4 (3)	C11—C12—H12	120.2
C17—C16—C15	121.2 (3)	C13—C12—H12	120.2
C11—C10—C9	120.6 (3)	C19—C20—C21	119.9 (3)
C11—C10—H10	119.7	C19—C20—H20	120.0
C9—C10—H10	119.7	C21—C20—H20	120.0
O3—C22—C15	109.7 (2)	C19—C18—C17	120.0 (3)
O3—C22—H22A	109.7	C19—C18—H18	120.0
C15—C22—H22A	109.7	C17—C18—H18	120.0
O3—C22—H22B	109.7	C2—C1—H1A	109.5
C15—C22—H22B	109.7	C2—C1—H1B	109.5
H22A—C22—H22B	108.2	H1A—C1—H1B	109.5
C18—C17—C16	120.6 (3)	C2—C1—H1C	109.5
C18—C17—H17	119.7	H1A—C1—H1C	109.5
C16—C17—H17	119.7	H1B—C1—H1C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.45	3.122 (3)	136
O3—H3A···O3ⁱⁱ	0.85	2.06	2.910 (5)	179.7
C4—H4···O1	0.93	2.55	2.909 (4)	104
C8—H8···O1	0.98	2.61	2.958 (3)	101
C1—H1A···O2ⁱⁱⁱ	0.96	2.63	3.557 (4)	161
C1—H1B···O2^iv	0.96	2.74	3.552 (4)	142
O3—H3B···C16ⁱⁱ	0.86	2.67	3.489 (4)	160.1
O3—H3B···C17ⁱⁱ	0.86	2.85	3.499 (4)	133.7

Symmetry codes: (i) x, y+1, z; (ii) −x, y, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₃NO₃S
M_r	381.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	90
a, b, c (Å)	39.4702 (16), 5.4270 (2), 17.4287 (7)
β (°)	91.028 (2)
V (Å³)	3732.7 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.4 × 0.16 × 0.14

Data collection
Diffractometer	Bruker SMART diffractometer with APEXII CCD detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22582, 4478, 3763
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.193, 1.13
No. of reflections	4478
No. of parameters	245
No. of restraints	15
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0794P)² + 19.2449P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.06, −0.64

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.45	3.122 (3)	135.9
O3—H3A···O3ⁱⁱ	0.85	2.06	2.910 (5)	179.7
C4—H4···O1	0.93	2.55	2.909 (4)	103.5
C8—H8···O1	0.98	2.61	2.958 (3)	100.9
C1—H1A···O2ⁱⁱⁱ	0.96	2.63	3.557 (4)	161.1
C1—H1B···O2^iv	0.96	2.74	3.552 (4)	142.2
O3—H3B···C16ⁱⁱ	0.86	2.67	3.489 (4)	160.1
O3—H3B···C17ⁱⁱ	0.86	2.85	3.499 (4)	133.7

Symmetry codes: (i) x, y+1, z; (ii) −x, y, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

The authors thank Tania Groutso for the data collection. The awards of an International Doctoral Scholarship from the University of Auckland and a New Zealand International Doctoral Research Scholarship from Education New Zealand (to STT) are greatly appreciated.

References

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