(R)-1-[(S)-(3-Cyano­thio­morpholino)carbon­yl]-2-methyl­propyl­aminium chloride dihydrate

Chen, P.; Liu, L.; Xiao, J.; Zhong, W.; Li, S.

doi:10.1107/S1600536809050624

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3281

doi:10.1107/S1600536809050624

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(R)-1-[(S)-(3-Cyanothiomorpholino)carbonyl]-2-methylpropylaminium chloride dihydrate

Pengfei Chen,^a,^b Lele Liu,^a Junhai Xiao,^b Wu Zhong ^b ^* and Song Li ^b

^aInner Mongolia Medical College, Hohhot 010059, People's Republic of China, and ^bBeijing Institute of Pharmacology and Toxicology, Beijing 100850, People's Republic of China
^*Correspondence e-mail: zhongwu@nic.bmi.ac.cn

(Received 15 October 2009; accepted 24 November 2009; online 28 November 2009)

In the title compound, C₁₀H₁₈N₃OS⁺·Cl⁻·2H₂O, the three C atoms of the isopropyl group are disordered and were refined using a split-site mode [occupancy ratio 0.53 (3):0.47 (3)]. In the crystal, the cations, anions and water molecules are connected via O—H⋯O, O—H⋯Cl, N—H⋯Cl and N—H⋯O hydrogen bonding.

Related literature

For N-substituted thiomorpholine derivatives as potentialdipeptidyl peptidase IV(DPP-IV) inhibitors, see: Engel et al. (2003 ). For their biological activity, see: Mu et al. (2006 ); Proost et al. (1998 ). For the synthesis, see: Li et al. (2007 )

Experimental

Crystal data

C₁₀H₁₈N₃OS⁺·Cl⁻·2H₂O
M_r = 299.82
Monoclinic, P 2₁
a = 9.6425 (19) Å
b = 6.8180 (14) Å
c = 12.082 (2) Å
β = 99.25 (3)°
V = 784.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.16 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.914, T_max = 0.942
6464 measured reflections
3554 independent reflections
2987 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.066
S = 1.00
3554 reflections
216 parameters
49 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 1544 Friedel pairs
Flack parameter: −0.03 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2ⁱ	0.96 (2)	1.89 (2)	2.838 (2)	169.3 (15)
N3—H3B⋯Cl1	0.97 (2)	2.37 (2)	3.3178 (16)	165.3 (15)
N3—H3C⋯O1ⁱⁱ	0.807 (18)	2.232 (18)	2.7891 (17)	126.6 (17)
N3—H3C⋯Cl1ⁱⁱ	0.807 (18)	2.599 (19)	3.2732 (16)	142.0 (16)
O2—H2A⋯Cl1ⁱ	0.85 (2)	2.37 (3)	3.2176 (15)	171 (2)
O2—H2B⋯O3	0.92 (2)	1.81 (2)	2.7186 (19)	171 (2)
O3—H3F⋯Cl1	0.82 (2)	2.31 (2)	3.1332 (15)	179 (2)
O3—H3G⋯O2ⁱ	0.86 (3)	2.02 (3)	2.873 (2)	173 (2)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050624/nc2164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050624/nc2164Isup2.hkl

checkCIF report

Comment top

N-substituted thiomorpholine derivatives are considered as a potential dipeptidyl peptidase IV(DPP-IV) (Engel et al., 2003) inhibitor. These compounds present various biological properties, for instance, effectively ameliorate hyperglycemia,hyperlipidemia and significantly increase β-cell mass and improve islet architecture (Mu et al., 2006). In Addition, DPP-4 inhibitors display a potential anti-HIV-1 activity (Proost et al., 1998). The crystal structure of the title compound was analyzed by X-ray diffraction to investigate its structure-activity relationships.

In the crystal structure molecule of the title compound (Fig.1) the cations and anions are linked via intermolecular N—H···Cl interactions. They are additionally connected to the crystal water molecules by N—H···O and O—H···Cl interactions (Fig. 2 and Table 1). The water molecules are linked by strong O—H···O hydrogen bonding into zigzag-chains that elongate in the direction of the crystallographic c axis (Fig. 2).

Related literature top

For N-substituted thiomorpholine derivatives as potentialdipeptidyl peptidase IV(DPP-IV) inhibitors, see: Engel et al. (2003). For their biological activity, see: Mu et al. (2006); Proost et al. (1998). For the synthesis, see: Li et al. (2007)

Experimental top

The title compound was synthesized according the reported procedure of Li et al.(2007). Colorless single crystals were obtained by slow evaporation of a solution in acetone.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Crystal structure of the title compound with the atomic numbering scheme.Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Crystal structure of the title compound with view along the b axis. Hydrogen bonding is shown as dashed lines.

(R)-1-[(S)-(3-Cyanothiomorpholino)carbonyl]-2-methylpropylaminium chloride dihydrate top

Crystal data top

C₁₀H₁₈N₃OS⁺·Cl⁻·2H₂O	F(000) = 320
M_r = 299.82	D_x = 1.270 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.6425 (19) Å	Cell parameters from 2714 reflections
b = 6.8180 (14) Å	θ = 3.0–27.9°
c = 12.082 (2) Å	µ = 0.38 mm⁻¹
β = 99.25 (3)°	T = 113 K
V = 784.0 (3) Å³	Block, colorless
Z = 2	0.24 × 0.20 × 0.16 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3554 independent reflections
Radiation source: rotating anode	2987 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.028
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 1.7°
ω and ϕ scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −8→8
T_min = 0.914, T_max = 0.942	l = −11→15
6464 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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0336P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3554 reflections	Δρ_max = 0.20 e Å⁻³
216 parameters	Δρ_min = −0.35 e Å⁻³
49 restraints	Absolute structure: Flack (1983), 1535 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (4)

Crystal data top

C₁₀H₁₈N₃OS⁺·Cl⁻·2H₂O	V = 784.0 (3) Å³
M_r = 299.82	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.6425 (19) Å	µ = 0.38 mm⁻¹
b = 6.8180 (14) Å	T = 113 K
c = 12.082 (2) Å	0.24 × 0.20 × 0.16 mm
β = 99.25 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3554 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2987 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.942	R_int = 0.028
6464 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	Δρ_max = 0.20 e Å⁻³
S = 1.00	Δρ_min = −0.35 e Å⁻³
3554 reflections	Absolute structure: Flack (1983), 1535 Friedel pairs
216 parameters	Absolute structure parameter: −0.03 (4)
49 restraints

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	−0.41733 (4)	0.64231 (8)	0.03966 (4)	0.03201 (12)
O1	−0.03965 (11)	0.5796 (2)	0.38313 (8)	0.0233 (3)
N1	−0.12007 (18)	0.2338 (3)	0.05250 (14)	0.0364 (4)
N2	−0.12711 (12)	0.6463 (2)	0.20239 (10)	0.0155 (3)
N3	0.10799 (15)	0.8983 (2)	0.42585 (11)	0.0158 (3)
H3A	0.186 (2)	0.986 (3)	0.4463 (14)	0.024*
H3B	0.1398 (19)	0.784 (3)	0.4706 (15)	0.024*
H3C	0.041 (2)	0.947 (3)	0.4483 (14)	0.024*
C1	−0.16317 (19)	0.3355 (3)	0.11428 (15)	0.0232 (4)
C2	−0.21136 (16)	0.4683 (3)	0.19675 (12)	0.0181 (3)
H2	−0.1927	0.4031	0.2718	0.022*
C3	−0.36913 (17)	0.5114 (3)	0.16917 (13)	0.0251 (4)
H3D	−0.3975	0.5895	0.2309	0.030*
H3E	−0.4214	0.3859	0.1648	0.030*
C4	−0.29541 (17)	0.8435 (3)	0.07232 (15)	0.0253 (4)
H4A	−0.3025	0.9325	0.0069	0.030*
H4B	−0.3208	0.9191	0.1361	0.030*
C5	−0.14514 (17)	0.7707 (3)	0.10221 (13)	0.0180 (3)
H5A	−0.1198	0.6951	0.0384	0.022*
H5B	−0.0809	0.8845	0.1156	0.022*
C6	−0.04067 (15)	0.6840 (2)	0.30047 (12)	0.0154 (3)
C7	0.06389 (15)	0.8528 (2)	0.30441 (11)	0.0148 (3)
H7A	0.0150	0.9647	0.2691	0.018*	0.53 (3)
H7B	0.0196	0.9649	0.2656	0.018*	0.47 (3)
C8	0.1874 (9)	0.8031 (14)	0.2407 (11)	0.024 (3)	0.53 (3)
H8	0.1468	0.7550	0.1642	0.028*	0.53 (3)
C9	0.2793 (11)	0.641 (2)	0.3005 (11)	0.041 (2)	0.53 (3)
H9A	0.3459	0.5962	0.2526	0.062*	0.53 (3)
H9B	0.2200	0.5310	0.3161	0.062*	0.53 (3)
H9C	0.3311	0.6917	0.3711	0.062*	0.53 (3)
C10	0.2733 (12)	0.9874 (18)	0.2277 (11)	0.047 (2)	0.53 (3)
H10A	0.3165	1.0345	0.3019	0.070*	0.53 (3)
H10B	0.2116	1.0893	0.1897	0.070*	0.53 (3)
H10C	0.3470	0.9566	0.1832	0.070*	0.53 (3)
C8'	0.1900 (8)	0.7874 (14)	0.2504 (11)	0.019 (3)	0.47 (3)
H8'	0.1524	0.7688	0.1690	0.023*	0.47 (3)
C9'	0.2515 (12)	0.5906 (16)	0.2911 (13)	0.034 (2)	0.47 (3)
H9D	0.3310	0.5595	0.2528	0.052*	0.47 (3)
H9E	0.1795	0.4887	0.2746	0.052*	0.47 (3)
H9F	0.2839	0.5964	0.3722	0.052*	0.47 (3)
C10'	0.3015 (10)	0.9447 (18)	0.2549 (12)	0.036 (2)	0.47 (3)
H10D	0.3581	0.9474	0.3299	0.053*	0.47 (3)
H10E	0.2564	1.0726	0.2385	0.053*	0.47 (3)
H10F	0.3622	0.9161	0.1992	0.053*	0.47 (3)
Cl1	0.21552 (4)	0.56119 (6)	0.61863 (3)	0.01970 (9)
O2	0.67759 (13)	0.6702 (2)	0.49074 (11)	0.0268 (3)
H2A	0.703 (2)	0.768 (4)	0.4543 (18)	0.040*
H2B	0.611 (2)	0.735 (4)	0.5235 (17)	0.040*
O3	0.47478 (13)	0.8267 (2)	0.59628 (12)	0.0324 (3)
H3F	0.407 (3)	0.756 (4)	0.6016 (18)	0.049*
H3G	0.436 (2)	0.934 (4)	0.5706 (18)	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0217 (2)	0.0299 (3)	0.0392 (3)	−0.00703 (19)	−0.01085 (17)	0.0057 (2)
O1	0.0302 (6)	0.0248 (7)	0.0141 (5)	−0.0081 (5)	0.0005 (4)	0.0054 (5)
N1	0.0515 (11)	0.0204 (10)	0.0419 (10)	−0.0008 (8)	0.0216 (8)	−0.0005 (7)
N2	0.0165 (6)	0.0134 (7)	0.0157 (6)	−0.0021 (6)	−0.0002 (5)	0.0013 (5)
N3	0.0151 (6)	0.0182 (8)	0.0143 (6)	−0.0016 (6)	0.0031 (5)	−0.0042 (5)
C1	0.0285 (9)	0.0151 (9)	0.0258 (8)	−0.0034 (7)	0.0040 (7)	0.0033 (7)
C2	0.0219 (8)	0.0168 (9)	0.0157 (7)	−0.0055 (6)	0.0031 (6)	0.0016 (6)
C3	0.0200 (8)	0.0262 (11)	0.0292 (9)	−0.0059 (7)	0.0045 (6)	−0.0007 (7)
C4	0.0210 (8)	0.0209 (10)	0.0309 (9)	−0.0011 (7)	−0.0046 (7)	0.0055 (8)
C5	0.0194 (8)	0.0163 (9)	0.0173 (8)	−0.0031 (6)	−0.0002 (6)	0.0055 (6)
C6	0.0159 (7)	0.0161 (9)	0.0145 (7)	0.0012 (6)	0.0029 (5)	−0.0016 (6)
C7	0.0149 (7)	0.0175 (9)	0.0115 (7)	−0.0009 (6)	0.0008 (5)	0.0001 (6)
C8	0.019 (4)	0.035 (4)	0.019 (4)	0.008 (3)	0.007 (3)	0.003 (3)
C9	0.022 (3)	0.065 (5)	0.039 (3)	0.015 (3)	0.011 (3)	0.006 (4)
C10	0.043 (4)	0.064 (5)	0.038 (4)	−0.028 (3)	0.021 (3)	−0.007 (3)
C8'	0.015 (4)	0.035 (5)	0.008 (3)	−0.011 (3)	0.000 (3)	−0.003 (3)
C9'	0.024 (3)	0.040 (4)	0.042 (4)	0.018 (3)	0.013 (3)	0.009 (3)
C10'	0.028 (3)	0.049 (4)	0.036 (4)	−0.012 (3)	0.022 (3)	−0.011 (3)
Cl1	0.01873 (17)	0.0176 (2)	0.02289 (18)	−0.00188 (16)	0.00372 (13)	0.00047 (16)
O2	0.0250 (6)	0.0215 (8)	0.0359 (7)	0.0045 (6)	0.0106 (5)	0.0060 (6)
O3	0.0219 (7)	0.0244 (8)	0.0526 (9)	−0.0029 (6)	0.0118 (6)	0.0001 (7)

Geometric parameters (Å, º) top

S1—C3	1.7965 (17)	C7—H7A	0.9601
S1—C4	1.8085 (18)	C7—H7B	0.9601
O1—C6	1.2251 (18)	C8—C9	1.523 (8)
N1—C1	1.145 (2)	C8—C10	1.527 (7)
N2—C6	1.3594 (18)	C8—H8	1.0000
N2—C2	1.456 (2)	C9—H9A	0.9800
N2—C5	1.465 (2)	C9—H9B	0.9800
N3—C7	1.4931 (18)	C9—H9C	0.9800
N3—H3A	0.96 (2)	C10—H10A	0.9800
N3—H3B	0.97 (2)	C10—H10B	0.9800
N3—H3C	0.807 (18)	C10—H10C	0.9800
C1—C2	1.476 (2)	C8'—C10'	1.514 (7)
C2—C3	1.533 (2)	C8'—C9'	1.517 (8)
C2—H2	1.0000	C8'—H8'	1.0000
C3—H3D	0.9900	C9'—H9D	0.9800
C3—H3E	0.9900	C9'—H9E	0.9800
C4—C5	1.519 (2)	C9'—H9F	0.9800
C4—H4A	0.9900	C10'—H10D	0.9800
C4—H4B	0.9900	C10'—H10E	0.9800
C5—H5A	0.9900	C10'—H10F	0.9800
C5—H5B	0.9900	O2—H2A	0.85 (2)
C6—C7	1.525 (2)	O2—H2B	0.92 (2)
C7—C8'	1.535 (7)	O3—H3F	0.82 (2)
C7—C8	1.555 (7)	O3—H3G	0.86 (3)

C3—S1—C4	96.81 (8)	C6—C7—C8'	109.4 (4)
C6—N2—C2	117.26 (13)	N3—C7—C8	114.3 (5)
C6—N2—C5	125.82 (14)	C6—C7—C8	112.0 (4)
C2—N2—C5	116.91 (12)	C8'—C7—C8	5.8 (8)
C7—N3—H3A	118.0 (10)	N3—C7—H7A	108.3
C7—N3—H3B	113.3 (11)	C6—C7—H7A	108.1
H3A—N3—H3B	101.0 (15)	C8'—C7—H7A	114.1
C7—N3—H3C	107.4 (13)	C8—C7—H7A	108.3
H3A—N3—H3C	107.0 (17)	N3—C7—H7B	110.4
H3B—N3—H3C	109.8 (17)	C6—C7—H7B	110.2
N1—C1—C2	177.1 (2)	C8'—C7—H7B	110.1
N2—C2—C1	108.01 (12)	C8—C7—H7B	104.3
N2—C2—C3	112.16 (14)	H7A—C7—H7B	3.9
C1—C2—C3	112.35 (14)	C9—C8—C10	111.2 (6)
N2—C2—H2	108.1	C9—C8—C7	110.9 (7)
C1—C2—H2	108.1	C10—C8—C7	110.1 (6)
C3—C2—H2	108.1	C9—C8—H8	108.2
C2—C3—S1	113.17 (11)	C10—C8—H8	108.2
C2—C3—H3D	108.9	C7—C8—H8	108.2
S1—C3—H3D	108.9	C10'—C8'—C9'	112.1 (6)
C2—C3—H3E	108.9	C10'—C8'—C7	112.7 (6)
S1—C3—H3E	108.9	C9'—C8'—C7	114.5 (7)
H3D—C3—H3E	107.8	C10'—C8'—H8'	105.6
C5—C4—S1	111.44 (13)	C9'—C8'—H8'	105.6
C5—C4—H4A	109.3	C7—C8'—H8'	105.6
S1—C4—H4A	109.3	C8'—C9'—H9D	109.5
C5—C4—H4B	109.3	C8'—C9'—H9E	109.5
S1—C4—H4B	109.3	H9D—C9'—H9E	109.5
H4A—C4—H4B	108.0	C8'—C9'—H9F	109.5
N2—C5—C4	111.57 (13)	H9D—C9'—H9F	109.5
N2—C5—H5A	109.3	H9E—C9'—H9F	109.5
C4—C5—H5A	109.3	C8'—C10'—H10D	109.5
N2—C5—H5B	109.3	C8'—C10'—H10E	109.5
C4—C5—H5B	109.3	H10D—C10'—H10E	109.5
H5A—C5—H5B	108.0	C8'—C10'—H10F	109.5
O1—C6—N2	121.61 (15)	H10D—C10'—H10F	109.5
O1—C6—C7	119.60 (13)	H10E—C10'—H10F	109.5
N2—C6—C7	118.67 (13)	H2A—O2—H2B	97 (2)
N3—C7—C6	105.67 (11)	H3F—O3—H3G	103 (2)
N3—C7—C8'	111.0 (5)

C6—N2—C2—C1	−114.30 (15)	N2—C6—C7—N3	162.20 (13)
C5—N2—C2—C1	66.80 (17)	O1—C6—C7—C8'	97.7 (6)
C6—N2—C2—C3	121.36 (15)	N2—C6—C7—C8'	−78.2 (6)
C5—N2—C2—C3	−57.54 (17)	O1—C6—C7—C8	103.3 (5)
N1—C1—C2—N2	49 (4)	N2—C6—C7—C8	−72.7 (5)
N1—C1—C2—C3	173 (4)	N3—C7—C8—C9	52.9 (9)
N2—C2—C3—S1	57.51 (16)	C6—C7—C8—C9	−67.3 (10)
C1—C2—C3—S1	−64.39 (17)	C8'—C7—C8—C9	−3 (8)
C4—S1—C3—C2	−54.02 (14)	N3—C7—C8—C10	−70.6 (9)
C3—S1—C4—C5	56.05 (13)	C6—C7—C8—C10	169.3 (7)
C6—N2—C5—C4	−118.33 (16)	C8'—C7—C8—C10	−127 (9)
C2—N2—C5—C4	60.48 (18)	N3—C7—C8'—C10'	−61.6 (9)
S1—C4—C5—N2	−61.99 (17)	C6—C7—C8'—C10'	−177.9 (8)
C2—N2—C6—O1	−4.4 (2)	C8—C7—C8'—C10'	64 (8)
C5—N2—C6—O1	174.41 (15)	N3—C7—C8'—C9'	68.0 (10)
C2—N2—C6—C7	171.52 (12)	C6—C7—C8'—C9'	−48.2 (11)
C5—N2—C6—C7	−9.7 (2)	C8—C7—C8'—C9'	−166 (9)
O1—C6—C7—N3	−21.81 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱ	0.96 (2)	1.89 (2)	2.838 (2)	169.3 (15)
N3—H3B···Cl1	0.97 (2)	2.37 (2)	3.3178 (16)	165.3 (15)
N3—H3C···O1ⁱⁱ	0.807 (18)	2.232 (18)	2.7891 (17)	126.6 (17)
N3—H3C···Cl1ⁱⁱ	0.807 (18)	2.599 (19)	3.2732 (16)	142.0 (16)
O2—H2A···Cl1ⁱ	0.85 (2)	2.37 (3)	3.2176 (15)	171 (2)
O2—H2B···O3	0.92 (2)	1.81 (2)	2.7186 (19)	171 (2)
O3—H3F···Cl1	0.82 (2)	2.31 (2)	3.1332 (15)	179 (2)
O3—H3G···O2ⁱ	0.86 (3)	2.02 (3)	2.873 (2)	173 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₈N₃OS⁺·Cl⁻·2H₂O
M_r	299.82
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	113
a, b, c (Å)	9.6425 (19), 6.8180 (14), 12.082 (2)
β (°)	99.25 (3)
V (Å³)	784.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.914, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	6464, 3554, 2987
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.066, 1.00
No. of reflections	3554
No. of parameters	216
No. of restraints	49
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.35
Absolute structure	Flack (1983), 1535 Friedel pairs
Absolute structure parameter	−0.03 (4)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱ	0.96 (2)	1.89 (2)	2.838 (2)	169.3 (15)
N3—H3B···Cl1	0.97 (2)	2.37 (2)	3.3178 (16)	165.3 (15)
N3—H3C···O1ⁱⁱ	0.807 (18)	2.232 (18)	2.7891 (17)	126.6 (17)
N3—H3C···Cl1ⁱⁱ	0.807 (18)	2.599 (19)	3.2732 (16)	142.0 (16)
O2—H2A···Cl1ⁱ	0.85 (2)	2.37 (3)	3.2176 (15)	171 (2)
O2—H2B···O3	0.92 (2)	1.81 (2)	2.7186 (19)	171 (2)
O3—H3F···Cl1	0.82 (2)	2.31 (2)	3.1332 (15)	179 (2)
O3—H3G···O2ⁱ	0.86 (3)	2.02 (3)	2.873 (2)	173 (2)

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

Acknowledgements

This work was supported by the National Special Program for Innovative Drugs (2009ZX09501-005).

References

Engel, M., Hoffmann, T., Wagner, L., Wermann, M., Heiser, U., Kiefersauer, R., Huber, R., Bode, W., Demuth, H. U. & Brandstetter, H. (2003). Proc. Natl Acad. Sci. USA, 100, 5063–5068. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, S., Zhong, W., Xiao, J. H., Ma, X. H., Wang, L. L., Liu, H. Y. & Zheng, Z. B. (2007). CN Patent CN200710090694.2. Google Scholar
Mu, J., Woods, J., Zhou, Y. P., Roy, R. S., Li, Z. H., Zycband, E., Feng, Y., Zhu, L., Li, C., Howard, A. D., Moller, D. E., Thornberry, N. A. & Zhang, B. B. (2006). Diabetes, 55, 1695–1704. Web of Science CrossRef PubMed CAS Google Scholar
Proost, P., Meester, I. D., Schols, D., Struyf, S., Lambeir, A. M., Wuyts, A., Opdenakker, G., Clercq, E. D., Scharpe, S. & Damme, J. V. (1998). J. Biol. Chem. 273, 7222–7227. Web of Science CrossRef CAS PubMed Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Page o3281

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

(R)-1-[(S)-(3-Cyano­thio­morpholino)carbon­yl]-2-methyl­propyl­aminium chloride dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(R)-1-[(S)-(3-Cyanothiomorpholino)carbonyl]-2-methylpropylaminium chloride dihydrate