Methyl 2-[(tert-but­oxy­carbon­yl)amino]-3-(3-methyl-2-sulfanyl­idene-2,3-dihydro-1H-imidazol-1-yl)propano­ate

Chan, C.-F.; Guo, Y.-C.; Huang, B.-H.; Chen, M.-J.

doi:10.1107/S1600536812043486

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3206

doi:10.1107/S1600536812043486

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Methyl 2-[(tert-butoxycarbonyl)amino]-3-(3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazol-1-yl)propanoate

Chin-Feng Chan,^a Yi-Cin Guo,^a Bor-Hunn Huang ^b and Ming-Jen Chen ^a ^*

^aDepartment of Applied Cosmetology and Graduate Institute of Cosmetic Science, Hungkuang University, Taichung 433, Taiwan, and ^bDepartment of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
^*Correspondence e-mail: mjchen@sunrise.hk.edu.tw

(Received 12 October 2012; accepted 19 October 2012; online 24 October 2012)

In the title compound, C₁₃H₂₁N₃O₄S, the mean plane of the –N(H)—C(=O)—O– group of the carbamate unit forms a dihedral angle of 64.7 (2)° with the mean plane of the –C—C(=O)—O– group of the ester unit. In the crystal, molecules are linked by N—H⋯O=C hydrogen bonds, forming chains along the c-axis direction.

Related literature

The title compound is a mercaptoimidazole derivative. For applications of mercaptoimidazole derivatives in the treatment of hyperpigmentation, see: Kasraee (2002 ); Kasraee et al. (2005 ) and for inhibiting tyrosinase, see: Liao et al. (2012 ). For typical bond lengths of intermolecular N—H⋯O=C hydrogen bonds, see: Taylor et al. (1984 ).

Experimental

Crystal data

C₁₃H₂₁N₃O₄S
M_r = 315.39
Monoclinic, P 2₁ /c
a = 8.7636 (1) Å
b = 19.1184 (2) Å
c = 9.6735 (2) Å
β = 98.485 (1)°
V = 1603.02 (4) Å³
Z = 4
Cu Kα radiation
μ = 1.97 mm⁻¹
T = 110 K
0.60 × 0.50 × 0.30 mm

Data collection

Agilent Xcalibur (Sapphire3, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.550, T_max = 1.000
12262 measured reflections
3093 independent reflections
2923 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.137
S = 1.05
3093 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1ⁱ	0.88	2.25	2.9819 (14)	140
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812043486/lh5544sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043486/lh5544Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043486/lh5544Isup3.cml

checkCIF report

Comment top

Methimazole causes hypopigmentation in some patients during the clinical oral antithyroid medication (Kasraee, 2002; Kasraee et al., 2005). Ergothioneine has a potent inhibition effect on inhibiting tyrosinase enzyme activity, resulting from the presence of the sulfur substituted imidazole ring (Liao et al., 2012). It shows that molecules with a mercaptoimidazole group have potential as depigmenting agents. The title compound (I) is the key intermediate for the synthesis of the amino acid derivatives containing methimazole moiety. Methimazole exists between the 2-thiol and 2-thione forms and has been observed to react in both guizes, depending upon the reaction conditions. Compound (I) is the nitrogen-substituted product from the 2-thione form.

Herein we report the synthesis and crystal structure of the title compound. The molecular structure of (I) is shown in Fig. 1. The essentially planar carbamate group (N3/C7/O1/O2) forms a dihedral angle of 64.7 (2)° with the mean plane of the carboxylate group (C6/C12/O3/O4). In the crystal, molecules are linked by N—H···O═C hydrogen bonds involving the amino and carbamate group forming chains along the c-axis direction. Intermolecular N—H···O═C hydrogen bonds are are highlighted in the literature by Taylor et al. (1984).

Related literature top

The title compound is a mercaptoimidazole derivative. For applications of mercaptoimidazole derivatives in the treatment of hyperpigmentation, see: Kasraee (2002); Kasraee et al. (2005) and for inhibiting tyrosinase, see: Liao et al. (2012). For typical bond lengths of intermolecular N—H···O═C hydrogen bonds, see: Taylor et al. (1984).

Experimental top

To a mixture of 1-methyl-2-mercaptoimidazole (390 mg, 3.4 mmole) and methyl 3-bromo-2-[(tert-butoxycarbonyl)amino]propanoate (970 mg, 3.4 mmol) in 17 ml of N,N-dimethylformamide was added potassium carbonate (940 mg, 6.8 mmole). The reaction mixture was stirred at 343 K for 1.5 h under N₂ atmosphere. The resulting mixture was partitioned between dichloromethane (70 ml) and H₂O (35 ml). The organic layer was dried over MgSO₄ and concentrated in vacuo. The residue was separated by chromatography over silica gel and eluted with hexane/ethyl acetate (3/7) to afford 776 mg of the title compound (I) in 72% yield. Single crystals suitable for X-ray measurements were obtained by recrystallization from a dichloromethane/hexane solution of the title compound at room temperature.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with ellipsoids for non-H atoms shown at the 50% probability level.

Methyl 2-[(tert-butoxycarbonyl)amino]-3-(3-methyl-2-sulfanylidene- 2,3-dihydro-1H-imidazol-1-yl)propanoate top

Crystal data top

C₁₃H₂₁N₃O₄S	-
M_r = 315.39	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 379 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 8.7636 (1) Å	Cell parameters from 9755 reflections
b = 19.1184 (2) Å	θ = 4.6–71.5°
c = 9.6735 (2) Å	µ = 1.97 mm⁻¹
β = 98.485 (1)°	T = 110 K
V = 1603.02 (4) Å³	Cube, colourless
Z = 4	0.60 × 0.50 × 0.30 mm
F(000) = 672

Data collection top

Agilent Xcalibur (Sapphire3, Gemini) diffractometer	3093 independent reflections
Radiation source: fine-focus sealed tube	2923 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 16.0690 pixels mm^-1	θ_max = 71.6°, θ_min = 4.6°
ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −23→23
T_min = 0.550, T_max = 1.000	l = −10→11
12262 measured 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.120P)²] where P = (F_o² + 2F_c²)/3
3093 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₃H₂₁N₃O₄S	V = 1603.02 (4) Å³
M_r = 315.39	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.7636 (1) Å	µ = 1.97 mm⁻¹
b = 19.1184 (2) Å	T = 110 K
c = 9.6735 (2) Å	0.60 × 0.50 × 0.30 mm
β = 98.485 (1)°

Data collection top

Agilent Xcalibur (Sapphire3, Gemini) diffractometer	3093 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2923 reflections with I > 2σ(I)
T_min = 0.550, T_max = 1.000	R_int = 0.019
12262 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	Δρ_max = 0.39 e Å⁻³
3093 reflections	Δρ_min = −0.53 e Å⁻³
190 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28–04-2010 CrysAlis171. NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S	0.73233 (4)	0.397097 (16)	0.68939 (3)	0.01934 (17)
O1	1.13487 (11)	0.21854 (5)	0.76481 (9)	0.0166 (2)
O2	1.21653 (11)	0.16902 (5)	0.97808 (10)	0.0159 (2)
O3	1.39031 (11)	0.39024 (5)	0.96950 (12)	0.0242 (3)
O4	1.20097 (10)	0.46673 (5)	0.89321 (11)	0.0185 (2)
N1	0.65404 (12)	0.27506 (6)	0.81002 (12)	0.0173 (3)
N2	0.85617 (12)	0.32536 (6)	0.92269 (12)	0.0154 (3)
N3	1.18007 (12)	0.28264 (5)	0.96527 (11)	0.0128 (3)
H3A	1.2174	0.2816	1.0548	0.015*
C1	0.51211 (16)	0.26296 (8)	0.71401 (16)	0.0257 (3)
H1A	0.5002	0.2993	0.6417	0.039*
H1B	0.4240	0.2645	0.7656	0.039*
H1C	0.5167	0.2170	0.6701	0.039*
C2	0.74673 (14)	0.33203 (7)	0.80813 (13)	0.0133 (3)
C3	0.70687 (16)	0.23359 (8)	0.92408 (16)	0.0237 (3)
H3B	0.6621	0.1909	0.9484	0.028*
C4	0.83277 (16)	0.26432 (8)	0.99458 (15)	0.0222 (3)
H4A	0.8938	0.2476	1.0773	0.027*
C5	0.98306 (14)	0.37429 (7)	0.95850 (14)	0.0150 (3)
H5A	1.0054	0.3794	1.0613	0.018*
H5B	0.9531	0.4207	0.9180	0.018*
C6	1.12846 (13)	0.34846 (6)	0.90267 (13)	0.0124 (3)
H6A	1.1017	0.3412	0.7996	0.015*
C7	1.17322 (13)	0.22218 (6)	0.89111 (13)	0.0117 (3)
C8	1.21603 (16)	0.09602 (6)	0.92637 (15)	0.0155 (3)
C9	1.32792 (18)	0.08866 (7)	0.82123 (18)	0.0255 (4)
H9A	1.4312	0.1032	0.8646	0.038*
H9B	1.2938	0.1183	0.7399	0.038*
H9C	1.3309	0.0398	0.7914	0.038*
C10	1.27314 (18)	0.05494 (7)	1.05848 (16)	0.0228 (3)
H10A	1.1998	0.0602	1.1251	0.034*
H10B	1.3743	0.0728	1.1004	0.034*
H10C	1.2821	0.0054	1.0351	0.034*
C11	1.05181 (16)	0.07481 (7)	0.86891 (15)	0.0215 (3)
H11A	0.9859	0.0809	0.9415	0.032*
H11B	1.0502	0.0257	0.8399	0.032*
H11C	1.0135	0.1042	0.7882	0.032*
C12	1.25754 (15)	0.40293 (6)	0.92748 (14)	0.0131 (3)
C13	1.31275 (16)	0.52315 (7)	0.90481 (17)	0.0236 (3)
H13A	1.2600	0.5673	0.8774	0.035*
H13B	1.3897	0.5137	0.8432	0.035*
H13C	1.3641	0.5266	1.0017	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0231 (3)	0.0120 (2)	0.0207 (3)	−0.00343 (11)	−0.00411 (17)	0.00477 (11)
O1	0.0231 (5)	0.0148 (5)	0.0116 (5)	−0.0038 (3)	0.0021 (4)	−0.0014 (3)
O2	0.0216 (5)	0.0103 (5)	0.0145 (5)	−0.0009 (3)	−0.0014 (4)	−0.0014 (3)
O3	0.0128 (5)	0.0217 (5)	0.0364 (6)	−0.0026 (4)	−0.0020 (4)	0.0038 (4)
O4	0.0153 (5)	0.0110 (5)	0.0281 (6)	−0.0027 (3)	−0.0001 (4)	−0.0003 (4)
N1	0.0109 (5)	0.0163 (6)	0.0243 (6)	−0.0033 (4)	0.0010 (4)	0.0038 (4)
N2	0.0115 (5)	0.0145 (6)	0.0198 (6)	−0.0016 (4)	0.0011 (4)	0.0042 (4)
N3	0.0147 (5)	0.0121 (5)	0.0108 (5)	0.0002 (4)	−0.0008 (4)	−0.0005 (4)
C1	0.0149 (7)	0.0260 (8)	0.0345 (9)	−0.0096 (5)	−0.0017 (6)	0.0024 (6)
C2	0.0113 (6)	0.0110 (6)	0.0178 (7)	0.0000 (4)	0.0031 (5)	−0.0004 (4)
C3	0.0182 (7)	0.0200 (7)	0.0335 (8)	−0.0042 (5)	0.0055 (6)	0.0119 (6)
C4	0.0175 (7)	0.0226 (7)	0.0264 (8)	−0.0010 (5)	0.0031 (5)	0.0125 (6)
C5	0.0114 (6)	0.0156 (7)	0.0173 (7)	−0.0015 (5)	0.0002 (5)	−0.0019 (5)
C6	0.0116 (6)	0.0129 (6)	0.0122 (6)	−0.0015 (4)	−0.0002 (5)	−0.0007 (5)
C7	0.0078 (5)	0.0122 (6)	0.0155 (6)	−0.0027 (4)	0.0022 (4)	0.0004 (5)
C8	0.0208 (7)	0.0078 (6)	0.0179 (7)	−0.0042 (5)	0.0028 (6)	−0.0017 (5)
C9	0.0321 (8)	0.0118 (6)	0.0366 (9)	−0.0032 (6)	0.0184 (7)	−0.0024 (6)
C10	0.0297 (7)	0.0129 (6)	0.0242 (7)	−0.0019 (5)	−0.0014 (6)	0.0028 (5)
C11	0.0231 (7)	0.0198 (7)	0.0200 (7)	−0.0105 (5)	−0.0019 (5)	0.0023 (5)
C12	0.0139 (6)	0.0127 (6)	0.0126 (6)	−0.0018 (4)	0.0010 (5)	−0.0008 (4)
C13	0.0189 (7)	0.0137 (6)	0.0369 (9)	−0.0064 (5)	−0.0004 (6)	0.0010 (6)

Geometric parameters (Å, º) top

S—C2	1.6852 (13)	C4—H4A	0.9500
O1—C7	1.2204 (16)	C5—C6	1.5370 (16)
O2—C7	1.3380 (16)	C5—H5A	0.9900
O2—C8	1.4825 (14)	C5—H5B	0.9900
O3—C12	1.1993 (17)	C6—C12	1.5301 (16)
O4—C12	1.3398 (15)	C6—H6A	1.0000
O4—C13	1.4502 (16)	C8—C11	1.5193 (18)
N1—C2	1.3605 (16)	C8—C9	1.5199 (19)
N1—C3	1.3819 (18)	C8—C10	1.5204 (19)
N1—C1	1.4567 (17)	C9—H9A	0.9800
N2—C2	1.3604 (17)	C9—H9B	0.9800
N2—C4	1.3890 (17)	C9—H9C	0.9800
N2—C5	1.4553 (16)	C10—H10A	0.9800
N3—C7	1.3571 (16)	C10—H10B	0.9800
N3—C6	1.4402 (16)	C10—H10C	0.9800
N3—H3A	0.8800	C11—H11A	0.9800
C1—H1A	0.9800	C11—H11B	0.9800
C1—H1B	0.9800	C11—H11C	0.9800
C1—H1C	0.9800	C13—H13A	0.9800
C3—C4	1.344 (2)	C13—H13B	0.9800
C3—H3B	0.9500	C13—H13C	0.9800

C7—O2—C8	121.10 (10)	C5—C6—H6A	108.1
C12—O4—C13	115.91 (10)	O1—C7—O2	126.64 (11)
C2—N1—C3	109.86 (11)	O1—C7—N3	124.20 (11)
C2—N1—C1	125.02 (12)	O2—C7—N3	109.16 (11)
C3—N1—C1	124.88 (12)	O2—C8—C11	109.28 (11)
C2—N2—C4	110.38 (11)	O2—C8—C9	110.05 (10)
C2—N2—C5	123.76 (11)	C11—C8—C9	113.60 (12)
C4—N2—C5	125.80 (11)	O2—C8—C10	102.62 (11)
C7—N3—C6	122.36 (10)	C11—C8—C10	110.26 (11)
C7—N3—H3A	118.8	C9—C8—C10	110.47 (12)
C6—N3—H3A	118.8	C8—C9—H9A	109.5
N1—C1—H1A	109.5	C8—C9—H9B	109.5
N1—C1—H1B	109.5	H9A—C9—H9B	109.5
H1A—C1—H1B	109.5	C8—C9—H9C	109.5
N1—C1—H1C	109.5	H9A—C9—H9C	109.5
H1A—C1—H1C	109.5	H9B—C9—H9C	109.5
H1B—C1—H1C	109.5	C8—C10—H10A	109.5
N2—C2—N1	105.34 (11)	C8—C10—H10B	109.5
N2—C2—S	126.68 (10)	H10A—C10—H10B	109.5
N1—C2—S	127.98 (10)	C8—C10—H10C	109.5
C4—C3—N1	107.92 (13)	H10A—C10—H10C	109.5
C4—C3—H3B	126.0	H10B—C10—H10C	109.5
N1—C3—H3B	126.0	C8—C11—H11A	109.5
C3—C4—N2	106.51 (12)	C8—C11—H11B	109.5
C3—C4—H4A	126.7	H11A—C11—H11B	109.5
N2—C4—H4A	126.7	C8—C11—H11C	109.5
N2—C5—C6	110.72 (10)	H11A—C11—H11C	109.5
N2—C5—H5A	109.5	H11B—C11—H11C	109.5
C6—C5—H5A	109.5	O3—C12—O4	124.96 (12)
N2—C5—H5B	109.5	O3—C12—C6	124.98 (11)
C6—C5—H5B	109.5	O4—C12—C6	110.05 (10)
H5A—C5—H5B	108.1	O4—C13—H13A	109.5
N3—C6—C12	110.47 (10)	O4—C13—H13B	109.5
N3—C6—C5	110.99 (10)	H13A—C13—H13B	109.5
C12—C6—C5	110.99 (10)	O4—C13—H13C	109.5
N3—C6—H6A	108.1	H13A—C13—H13C	109.5
C12—C6—H6A	108.1	H13B—C13—H13C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.88	2.25	2.9819 (14)	140

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₂₁N₃O₄S
M_r	315.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	110
a, b, c (Å)	8.7636 (1), 19.1184 (2), 9.6735 (2)
β (°)	98.485 (1)
V (Å³)	1603.02 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.60 × 0.50 × 0.30

Data collection
Diffractometer	Agilent Xcalibur (Sapphire3, Gemini) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.550, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12262, 3093, 2923
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.137, 1.05
No. of reflections	3093
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.53

Computer programs: CrysAlis PRO (Agilent, 2010), 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···O1ⁱ	0.88	2.25	2.9819 (14)	139.9

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

We gratefully acknowledge financial support in part from the National Science Council, Taiwan (NSC 99–2119-M-241-001-MY2). Helpful comments from the reviewers are also greatly appreciated.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Kasraee, B. (2002). J. Invest. Dermatol. 118, 205–207. Web of Science CrossRef PubMed CAS Google Scholar
Kasraee, B., Handjani, F., Parhizgar, A., Omrani, G. R., Fallahi, M. R., Amini, M., Nikbakhsh, M., Tran, C., Hügin, A., Sorg, O. & Saurat, J.-H. (2005). Dermatology, 211, 360–362. Web of Science CrossRef PubMed CAS Google Scholar
Liao, W. C., Wu, W. H., Tsai, P.-C., Wang, H.-F., Liu, Y.-H. & Chan, C.-F. (2012). Appl. Biochem. Biotechnol. 166, 259–267. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taylor, R., Kennard, O. & Versichel, W. (1984). Acta Cryst. B40, 280–288. CrossRef CAS Web of Science IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3206

doi:10.1107/S1600536812043486

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

Methyl 2-[(tert-but­­oxy­carbon­yl)amino]-3-(3-methyl-2-sulfanyl­­idene-2,3-di­hydro-1H-imidazol-1-yl)propano­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 2-[(tert-butoxycarbonyl)amino]-3-(3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazol-1-yl)propanoate