Methyl 2-[(tert-but-oxy-carbon-yl)amino]-3-(3-methyl-2-sulfanyl-idene-2,3-dihydro-1H-imidazol-1-yl)propano-ate.

In the title compound, C(13)H(21)N(3)O(4)S, 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, mol-ecules 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 = 315.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.137

S = 1.05

3093 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.53 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043486/lh5544sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043486/lh5544Isup3.cml

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

C13H21N3O4S	-
Mr = 315.39	Dx = 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

Agilent Xcalibur (Sapphire3, Gemini) diffractometer	3093 independent reflections
Radiation source: fine-focus sealed tube	2923 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 16.0690 pixels mm-1	θmax = 71.6°, θmin = 4.6°
ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −23→23
Tmin = 0.550, Tmax = 1.000	l = −10→11
12262 measured reflections

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(Fo2) + (0.120P)2] where P = (Fo2 + 2Fc2)/3
3093 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.53 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .