Monoclinic modification of N-[(1,1-dimethyl­ethoxy)carbon­yl]-3-[(R)-prop-2-en-1-ylsulfin­yl]-(R)-alanine ethyl ester at 200 (1) K

Singh, S.P.; Verdu, M.J.; Lough, A.J.; Schwan, A.L.

doi:10.1107/S1600536809019023

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1385-o1386

doi:10.1107/S1600536809019023

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Monoclinic modification of N-[(1,1-dimethylethoxy)carbonyl]-3-[(R)-prop-2-en-1-ylsulfinyl]-(R)-alanine ethyl ester at 200 (1) K

Suneel P. Singh,^a Marcus J. Verdu,^a Alan J. Lough ^b ^* and Adrian L. Schwan ^a

^aDepartment of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1, and ^bDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 15 May 2009; accepted 19 May 2009; online 23 May 2009)

In the monoclinic polymorph of the title compound, C₁₃H₂₃NO₅S, intermolecular N—H⋯O hydrogen bonds link molecules into one-dimensional chains along [100]. The atoms of the terminal propenyl group are disordered over two sets of sites with refined occupancies of 0.69 (2) and 0.31 (2).

Related literature

For the crystal structure of the triclinic modification of the title compound at 120 (1) K see the paper which follows: Singh et al. (2009 ). For background information on chiral sulfoxides, see: Rose et al. (2005 ); Fernandez & Khiar, (2003 ); Olbe et al., 2003 . For synthetic details, see: O'Donnell & Schwan (2003 ). For related crystal structures see: Allain et al. (1980 ); Nakamura et al. (1996 ). For temperature-dependent phase transition in cysteine, see: Paukov et al. (2007 ), Kolesov et al. (2008 ).

Experimental

Crystal data

C₁₃H₂₃NO₅S
M_r = 305.38
Monoclinic, P 2₁
a = 5.1859 (6) Å
b = 11.5202 (18) Å
c = 14.009 (2) Å
β = 96.396 (8)°
V = 831.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 200 K
0.38 × 0.12 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.711, T_max = 0.974
3908 measured reflections
2397 independent reflections
1844 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.164
S = 1.05
2397 reflections
196 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 898 Friedel pairs
Flack parameter: −0.08 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.88	2.20	2.967 (5)	145
Symmetry code: (i) x+1, y, z.

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019023/hb2978sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019023/hb2978Isup2.hkl

checkCIF report

Comment top

A number of biologically significant molecules have a chiral sulfoxide functionality in their structure which is important for stereochemically dependent biological actions like metabolism and enzyme inhibition (Rose et al., 2005). Owing to the existence of pharmacological and toxicological differences between stereoisomers, chiral recognition has now become an integral part of drug research and development. Therefore, there has been a great interest in the synthesis of optically pure sulfoxides in recent years (Fernandez & Khiar, 2003). For example, the chiral switch drug esomeprazole [(S) isomer of omeprazole], the first single-optical-isomer gastric proton pump inhibitor (PPI), generally provides better acid control than current racemic PPIs and has a favourable pharmacokinetic profile relative to omeprazole (Olbe et al., 2003). However, only few examples of crystal structures of chirally pure cysteinyl sulfoxides have been reported in the literature (Nakamura et al., 1996). Moreover, temperature dependent phase trasitions in the crystal structures of cysteinyl sulfoxides are unknown till date (Paukov et al., 2007 and Kolesov et al., 2008).

The molecular structure of the title compound, (I), is shown in Fig. 1. In the crystal structure, intermolecular N—H···O hydrogen bonds link molecules into one-dimensional chains along [100] (Table 1, Fig. 2). Data for the title compound (using the same crystal) were also collected at 120 (1) K and the crystal structure solves and refines in the triclinic space group P1 (Singh et al., 2009).

Related literature top

For the crystal structure of the triclinic modification of the title compound at 120 (1) K see the paper which follows: Singh et al. (2009). For background information on chiral sulfoxides, see: Rose et al. (2005); Fernandez & Khiar, (2003); Olbe et al., 2003. For synthetic details, see: O'Donnell & Schwan (2003). For related crystal structures see: Allain et al. (1980); Nakamura et al. (1996). For temperature-dependent phase transition in cysteine, see: Paukov et al. (2007), Kolesov et al. (2008).

Experimental top

The N-protected amino acid derivative 1 (Fig. 3) was synthesized following a reported procedure. N-Boc-Alliin-OEt 2 was also synthesized by following the described procedure for its benzyl analog (O'Donnell and Schwan, 2003). Rerystallization from ethyl acetate and hexanes gave major diastereomer (R_C, R_S) of 2 as white solid, which was then dissolved in ethyl acetate and hexanes (9:1) and the solvent was allowed to evaporate slowly for several days to give white crystals of the major diastereomer (R_C,R_S) of 2.

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I): displacement elllipsoids are drawn at the 30% probabilty level. The minor disorder component is not shown.
	Fig. 2. Part of the crystal structure of (I) with hydrogen bonds shown as dashed lines.
	Fig. 3. The synthetic scheme.

N-[(1,1-dimethylethoxy)carbonyl]-3-[(R)-prop-2-en-1-ylsulfinyl]- (R)-alanine ethyl ester top

Crystal data top

C₁₃H₂₃NO₅S	F(000) = 328
M_r = 305.38	D_x = 1.219 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3908 reflections
a = 5.1859 (6) Å	θ = 2.9–25.0°
b = 11.5202 (18) Å	µ = 0.21 mm⁻¹
c = 14.009 (2) Å	T = 200 K
β = 96.396 (8)°	Needle, colourless
V = 831.7 (2) Å³	0.38 × 0.12 × 0.12 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	2397 independent reflections
Radiation source: fine-focus sealed tube	1844 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 2.9°
ϕ scans and ω scans with κ offsets	h = −6→6
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −12→13
T_min = 0.711, T_max = 0.974	l = −14→16
3908 measured reflections

Refinement top

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)] = 0.059	H-atom parameters constrained
wR(F²) = 0.164	w = 1/[σ²(F_o²) + (0.0816P)² + 0.1385P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.002
2397 reflections	Δρ_max = 0.30 e Å⁻³
196 parameters	Δρ_min = −0.22 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 898 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.08 (15)

Crystal data top

C₁₃H₂₃NO₅S	V = 831.7 (2) Å³
M_r = 305.38	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.1859 (6) Å	µ = 0.21 mm⁻¹
b = 11.5202 (18) Å	T = 200 K
c = 14.009 (2) Å	0.38 × 0.12 × 0.12 mm
β = 96.396 (8)°

Data collection top

Nonius KappaCCD diffractometer	2397 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1844 reflections with I > 2σ(I)
T_min = 0.711, T_max = 0.974	R_int = 0.070
3908 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.164	Δρ_max = 0.30 e Å⁻³
S = 1.05	Δρ_min = −0.22 e Å⁻³
2397 reflections	Absolute structure: Flack (1983), 898 Friedel pairs
196 parameters	Absolute structure parameter: −0.08 (15)
4 restraints

Special details top

Experimental. Absorption correction: multi-scan from symmetry-related measurements (SORTAV; Blessing, 1995)

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	0.4365 (2)	0.46507 (13)	0.25026 (8)	0.0632 (4)
O1	0.1763 (5)	0.4581 (4)	0.2851 (3)	0.0810 (10)
O2	0.6209 (19)	0.7332 (5)	0.4815 (4)	0.175 (3)
O3	0.6089 (8)	0.8717 (4)	0.3748 (3)	0.0850 (11)
O4	0.0034 (6)	0.7655 (3)	0.2141 (2)	0.0667 (9)
O5	0.2554 (5)	0.8446 (3)	0.1080 (2)	0.0656 (9)
N1	0.4391 (7)	0.7397 (4)	0.2270 (3)	0.0576 (10)
H1	0.5784	0.7447	0.1966	0.069*
C1	0.6118 (9)	0.5732 (4)	0.3246 (4)	0.0578 (12)
H1A	0.6416	0.5449	0.3916	0.069*
H1B	0.7828	0.5871	0.3015	0.069*
C2	0.4583 (9)	0.6867 (4)	0.3214 (3)	0.0594 (12)
H2A	0.2780	0.6674	0.3351	0.071*
C3	0.5757 (12)	0.7652 (5)	0.4014 (4)	0.0775 (16)
C4	0.7307 (14)	0.9553 (8)	0.4454 (5)	0.1019 (19)
H4A	0.6164	1.0237	0.4490	0.122*
H4B	0.7574	0.9189	0.5097	0.122*
C5	0.9780 (13)	0.9914 (8)	0.4162 (6)	0.116 (3)
H5A	1.0601	1.0474	0.4627	0.174*
H5B	0.9502	1.0276	0.3526	0.174*
H5C	1.0909	0.9235	0.4135	0.174*
C6	0.628 (4)	0.3423 (8)	0.2976 (17)	0.067 (5)	0.694 (18)
H6A	0.8146	0.3592	0.2950	0.080*	0.694 (18)
H6B	0.6012	0.3302	0.3657	0.080*	0.694 (18)
C7	0.557 (2)	0.2340 (8)	0.2422 (9)	0.082 (3)	0.694 (18)
H7	0.6299	0.2247	0.1833	0.098*	0.694 (18)
C8	0.406 (2)	0.1516 (9)	0.2657 (9)	0.100 (4)	0.694 (18)
H8A	0.3285	0.1565	0.3238	0.120*	0.694 (18)
H8B	0.3740	0.0861	0.2249	0.120*	0.694 (18)
C6A	0.600 (8)	0.3431 (15)	0.312 (3)	0.057 (13)*	0.306 (18)
H6A1	0.7852	0.3428	0.3015	0.069*	0.306 (18)
H6A2	0.5896	0.3502	0.3824	0.069*	0.306 (18)
C7A	0.474 (5)	0.233 (2)	0.2760 (18)	0.076 (9)*	0.306 (18)
H7A	0.3078	0.2138	0.2940	0.091*	0.306 (18)
C8A	0.582 (6)	0.161 (3)	0.2209 (17)	0.100 (9)*	0.306 (18)
H8A1	0.7483	0.1786	0.2021	0.120*	0.306 (18)
H8A2	0.4950	0.0921	0.1994	0.120*	0.306 (18)
C9	0.2142 (8)	0.7809 (4)	0.1855 (3)	0.0542 (11)
C10	0.0367 (8)	0.8905 (5)	0.0423 (4)	0.0668 (14)
C11	0.1753 (10)	0.9514 (7)	−0.0349 (4)	0.0905 (18)
H11A	0.2817	1.0150	−0.0056	0.136*
H11C	0.0462	0.9825	−0.0848	0.136*
H11D	0.2866	0.8956	−0.0637	0.136*
C12	−0.1300 (11)	0.7915 (5)	−0.0014 (4)	0.0801 (16)
H12C	−0.2007	0.7478	0.0497	0.120*
H12D	−0.0241	0.7399	−0.0367	0.120*
H12A	−0.2729	0.8229	−0.0456	0.120*
C13	−0.1142 (9)	0.9761 (5)	0.0933 (4)	0.0732 (13)
H13C	−0.2131	0.9352	0.1386	0.110*
H13D	−0.2339	1.0182	0.0465	0.110*
H13A	0.0053	1.0312	0.1284	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0581 (6)	0.0632 (7)	0.0675 (7)	−0.0011 (7)	0.0036 (5)	0.0038 (7)
O1	0.0487 (16)	0.079 (2)	0.114 (3)	−0.005 (2)	0.0032 (16)	0.000 (3)
O2	0.370 (10)	0.077 (3)	0.064 (3)	0.004 (5)	−0.035 (4)	−0.003 (3)
O3	0.108 (3)	0.077 (3)	0.070 (2)	−0.019 (2)	0.0107 (19)	−0.002 (2)
O4	0.0447 (16)	0.076 (2)	0.080 (2)	0.0025 (17)	0.0113 (15)	0.0132 (17)
O5	0.0517 (17)	0.083 (2)	0.062 (2)	0.0055 (17)	0.0057 (13)	0.0213 (18)
N1	0.044 (2)	0.065 (3)	0.064 (2)	0.0082 (19)	0.0095 (16)	0.006 (2)
C1	0.052 (2)	0.059 (3)	0.062 (3)	−0.004 (2)	0.004 (2)	0.004 (2)
C2	0.057 (3)	0.066 (3)	0.056 (3)	0.006 (2)	0.014 (2)	0.008 (2)
C3	0.102 (4)	0.067 (4)	0.063 (4)	0.022 (3)	0.003 (3)	0.004 (3)
C4	0.116 (5)	0.100 (5)	0.090 (4)	−0.014 (5)	0.011 (3)	−0.023 (4)
C5	0.089 (4)	0.140 (8)	0.115 (5)	−0.022 (5)	−0.005 (4)	−0.028 (5)
C6	0.056 (6)	0.058 (7)	0.085 (9)	−0.004 (4)	0.005 (8)	0.005 (4)
C7	0.100 (8)	0.062 (7)	0.084 (7)	0.010 (6)	0.015 (6)	0.005 (6)
C8	0.117 (9)	0.071 (7)	0.105 (8)	−0.017 (6)	−0.021 (6)	0.007 (6)
C9	0.047 (3)	0.054 (3)	0.061 (3)	0.001 (2)	0.004 (2)	−0.002 (2)
C10	0.049 (2)	0.078 (4)	0.072 (3)	0.008 (3)	0.001 (2)	0.014 (3)
C11	0.075 (3)	0.123 (5)	0.073 (3)	0.005 (4)	0.002 (2)	0.033 (4)
C12	0.079 (3)	0.078 (4)	0.081 (4)	0.012 (3)	−0.003 (3)	−0.004 (3)
C13	0.064 (3)	0.061 (3)	0.092 (3)	−0.001 (3)	−0.002 (2)	0.003 (3)

Geometric parameters (Å, º) top

S1—O1	1.487 (3)	C6—H6A	0.9900
S1—C1	1.803 (5)	C6—H6B	0.9900
S1—C6	1.813 (6)	C7—C8	1.296 (12)
S1—C6A	1.813 (7)	C7—H7	0.9500
O2—C3	1.179 (7)	C8—H8A	0.9500
O3—C3	1.300 (7)	C8—H8B	0.9500
O3—C4	1.471 (8)	C6A—C7A	1.493 (14)
O4—C9	1.218 (5)	C6A—H6A1	0.9900
O5—C9	1.347 (6)	C6A—H6A2	0.9900
O5—C10	1.477 (5)	C7A—C8A	1.296 (13)
N1—C9	1.331 (6)	C7A—H7A	0.9500
N1—C2	1.450 (6)	C8A—H8A1	0.9500
N1—H1	0.8800	C8A—H8A2	0.9500
C1—C2	1.529 (7)	C10—C13	1.491 (8)
C1—H1A	0.9900	C10—C12	1.518 (8)
C1—H1B	0.9900	C10—C11	1.534 (8)
C2—C3	1.514 (8)	C11—H11A	0.9800
C2—H2A	1.0000	C11—H11C	0.9800
C4—C5	1.450 (10)	C11—H11D	0.9800
C4—H4A	0.9900	C12—H12C	0.9800
C4—H4B	0.9900	C12—H12D	0.9800
C5—H5A	0.9800	C12—H12A	0.9800
C5—H5B	0.9800	C13—H13C	0.9800
C5—H5C	0.9800	C13—H13D	0.9800
C6—C7	1.494 (13)	C13—H13A	0.9800

O1—S1—C1	105.4 (2)	C8—C7—H7	116.5
O1—S1—C6	108.6 (9)	C6—C7—H7	116.5
C1—S1—C6	96.2 (4)	C7—C8—H8A	120.0
O1—S1—C6A	101.1 (18)	C7—C8—H8B	120.0
C1—S1—C6A	94.6 (9)	H8A—C8—H8B	120.0
C3—O3—C4	119.1 (5)	C7A—C6A—S1	109.5 (16)
C9—O5—C10	121.2 (3)	C7A—C6A—H6A1	109.8
C9—N1—C2	121.1 (4)	S1—C6A—H6A1	109.8
C9—N1—H1	119.5	C7A—C6A—H6A2	109.8
C2—N1—H1	119.5	S1—C6A—H6A2	109.8
C2—C1—S1	110.3 (3)	H6A1—C6A—H6A2	108.2
C2—C1—H1A	109.6	C8A—C7A—C6A	123 (4)
S1—C1—H1A	109.6	C8A—C7A—H7A	118.6
C2—C1—H1B	109.6	C6A—C7A—H7A	118.6
S1—C1—H1B	109.6	C7A—C8A—H8A1	120.0
H1A—C1—H1B	108.1	C7A—C8A—H8A2	120.0
N1—C2—C3	113.9 (4)	H8A1—C8A—H8A2	120.0
N1—C2—C1	111.7 (4)	O4—C9—N1	125.4 (4)
C3—C2—C1	108.9 (4)	O4—C9—O5	125.0 (4)
N1—C2—H2A	107.4	N1—C9—O5	109.6 (4)
C3—C2—H2A	107.4	O5—C10—C13	110.2 (4)
C1—C2—H2A	107.4	O5—C10—C12	110.3 (4)
O2—C3—O3	123.3 (6)	C13—C10—C12	112.6 (4)
O2—C3—C2	122.6 (6)	O5—C10—C11	102.5 (3)
O3—C3—C2	114.0 (5)	C13—C10—C11	110.3 (5)
C5—C4—O3	109.0 (5)	C12—C10—C11	110.5 (5)
C5—C4—H4A	109.9	C10—C11—H11A	109.5
O3—C4—H4A	109.9	C10—C11—H11C	109.5
C5—C4—H4B	109.9	H11A—C11—H11C	109.5
O3—C4—H4B	109.9	C10—C11—H11D	109.5
H4A—C4—H4B	108.3	H11A—C11—H11D	109.5
C4—C5—H5A	109.5	H11C—C11—H11D	109.5
C4—C5—H5B	109.5	C10—C12—H12C	109.5
H5A—C5—H5B	109.5	C10—C12—H12D	109.5
C4—C5—H5C	109.5	H12C—C12—H12D	109.5
H5A—C5—H5C	109.5	C10—C12—H12A	109.5
H5B—C5—H5C	109.5	H12C—C12—H12A	109.5
C7—C6—S1	111.5 (7)	H12D—C12—H12A	109.5
C7—C6—H6A	109.3	C10—C13—H13C	109.5
S1—C6—H6A	109.3	C10—C13—H13D	109.5
C7—C6—H6B	109.3	H13C—C13—H13D	109.5
S1—C6—H6B	109.3	C10—C13—H13A	109.5
H6A—C6—H6B	108.0	H13C—C13—H13A	109.5
C8—C7—C6	126.9 (18)	H13D—C13—H13A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.88	2.20	2.967 (5)	145

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₂₃NO₅S
M_r	305.38
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	200
a, b, c (Å)	5.1859 (6), 11.5202 (18), 14.009 (2)
β (°)	96.396 (8)
V (Å³)	831.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.38 × 0.12 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.711, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	3908, 2397, 1844
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.164, 1.05
No. of reflections	2397
No. of parameters	196
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.22
Absolute structure	Flack (1983), 898 Friedel pairs
Absolute structure parameter	−0.08 (15)

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.88	2.20	2.967 (5)	145

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors wish to acknowledge NSERC Canada and the University of Toronto for funding and the donors of the American Chemical Society Petroleum Research Fund for partial support of this research

References

Allain, A., Kubiak, M., Jezowska-Trzebiatowska, B., Kozlowskai, H. & Glowiak, T. (1980). Inorg. Chim. Acta, 46, 127–133. CSD CrossRef CAS Web of Science Google Scholar
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Volume 65| Part 6| June 2009| Pages o1385-o1386

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

Monoclinic modification of N-[(1,1-di­methyl­eth­oxy)carbon­yl]-3-[(R)-prop-2-en-1-ylsulfin­yl]-(R)-alanine ethyl ester at 200 (1) K

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Monoclinic modification of N-[(1,1-dimethylethoxy)carbonyl]-3-[(R)-prop-2-en-1-ylsulfinyl]-(R)-alanine ethyl ester at 200 (1) K