Monoclinic modification of N-[(1,1-dimethyl-ethoxy)carbon-yl]-3-[(R)-prop-2-en-1-ylsulfin-yl]-(R)-alanine ethyl ester at 200 (1) K.

In the monoclinic polymorph of the title compound, C(13)H(23)NO(5)S, inter-molecular N-H⋯O hydrogen bonds link mol-ecules 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 = 305.38

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.164

S = 1.05

2397 reflections

196 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 898 Friedel pairs

Flack parameter: −0.08 (15)

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.

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

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

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

C13H23NO5S	F(000) = 328
Mr = 305.38	Dx = 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

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

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(Fo2) + (0.0816P)2 + 0.1385P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
2397 reflections	Δρmax = 0.30 e Å−3
196 parameters	Δρmin = −0.22 e Å−3
4 restraints	Absolute structure: Flack (1983), 898 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.08 (15)

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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

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

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) .