Butyl 2-(piperidine-1-carbothio­ylsulfan­yl)acetate

In the title mol­ecule, C₁₂H₂₁NO₂S₂, the piperidine ring adopts a chair conformation. In the crystal structure, an inter­molecular C—H...S hydrogen bond contributes to the stability.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.138
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A    ..  S1      ..       2.95 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Butyl 2-(piperidine-1-carbothioylsulfanyl)acetate

Crystal data

C12H21NO2S2	F(000) = 592
Mr = 275.42	Dx = 1.286 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.504 (3) Å	Cell parameters from 2040 reflections
b = 24.123 (12) Å	θ = 2.4–23.0°
c = 9.506 (5) Å	µ = 0.37 mm^−1
β = 107.513 (7)°	T = 273 K
V = 1422.3 (12) Å^3	Plate, colorless
Z = 4	0.36 × 0.24 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer	2769 independent reflections
Radiation source: fine-focus sealed tube	1953 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 26.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	h = −8→8
Tmin = 0.879, Tmax = 0.972	k = −29→29
8173 measured reflections	l = −6→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0833P)^2 + 0.0758P] where P = (Fo^2 + 2Fc^2)/3
2769 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	1.2478 (4)	−0.02321 (12)	0.7652 (3)	0.0681 (8)
H1A	1.3431	0.0087	0.7844	0.082*
H1B	1.2892	−0.0475	0.6970	0.082*
C2	1.2674 (5)	−0.05344 (12)	0.9064 (3)	0.0747 (8)
H2A	1.2372	−0.0280	0.9768	0.090*
H2B	1.4141	−0.0667	0.9476	0.090*
C3	1.1140 (5)	−0.10195 (12)	0.8828 (3)	0.0737 (8)
H3A	1.1196	−0.1181	0.9774	0.088*
H3B	1.1577	−0.1301	0.8248	0.088*
C4	0.8852 (5)	−0.08365 (12)	0.8037 (3)	0.0705 (8)
H4A	0.7920	−0.1159	0.7795	0.085*
H4B	0.8333	−0.0599	0.8682	0.085*
C5	0.8767 (5)	−0.05275 (10)	0.6648 (3)	0.0657 (7)
H5A	0.9177	−0.0772	0.5969	0.079*
H5B	0.7309	−0.0399	0.6176	0.079*
C6	0.9636 (4)	0.04736 (9)	0.7047 (2)	0.0483 (6)
C7	0.6509 (4)	0.12928 (11)	0.6650 (3)	0.0619 (7)
H7A	0.5084	0.1363	0.6737	0.074*
H7B	0.7551	0.1412	0.7564	0.074*
C8	0.6801 (4)	0.16428 (10)	0.5411 (3)	0.0571 (6)
C9	0.7264 (5)	0.25895 (12)	0.4813 (4)	0.0753 (8)
H9A	0.6155	0.2868	0.4714	0.090*
H9B	0.7074	0.2424	0.3852	0.090*
C10	0.9456 (5)	0.28531 (12)	0.5363 (4)	0.0774 (9)
H10A	0.9524	0.3158	0.4715	0.093*
H10B	0.9631	0.3006	0.6336	0.093*
C11	1.1290 (5)	0.24686 (12)	0.5454 (3)	0.0750 (8)
H11A	1.2628	0.2666	0.5897	0.090*
H11B	1.1222	0.2165	0.6107	0.090*
C12	1.1354 (5)	0.22341 (15)	0.4029 (4)	0.0971 (11)
H12A	1.0074	0.2020	0.3602	0.146*
H12B	1.2598	0.2001	0.4190	0.146*
H12C	1.1431	0.2530	0.3371	0.146*
N1	1.0246 (3)	−0.00510 (8)	0.7005 (2)	0.0550 (5)
O1	0.6723 (4)	0.14809 (8)	0.4213 (2)	0.0807 (6)
O2	0.7074 (3)	0.21661 (7)	0.5855 (2)	0.0687 (5)
S1	1.13068 (11)	0.10062 (3)	0.76094 (9)	0.0683 (3)
S2	0.68005 (11)	0.05665 (3)	0.64571 (8)	0.0663 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0606 (16)	0.0588 (16)	0.090 (2)	0.0017 (13)	0.0302 (15)	−0.0040 (14)
C2	0.0705 (19)	0.0688 (19)	0.072 (2)	0.0130 (14)	0.0021 (15)	−0.0017 (15)
C3	0.098 (2)	0.0626 (18)	0.0588 (17)	0.0052 (15)	0.0202 (16)	0.0103 (14)
C4	0.082 (2)	0.0532 (15)	0.084 (2)	−0.0147 (14)	0.0363 (16)	−0.0044 (15)
C5	0.0711 (18)	0.0492 (15)	0.0660 (18)	−0.0077 (12)	0.0043 (14)	−0.0056 (12)
C6	0.0542 (14)	0.0513 (13)	0.0406 (13)	−0.0082 (10)	0.0162 (10)	0.0044 (10)
C7	0.0637 (16)	0.0616 (16)	0.0646 (17)	0.0075 (13)	0.0257 (13)	0.0083 (13)
C8	0.0606 (16)	0.0534 (15)	0.0581 (17)	0.0085 (12)	0.0190 (12)	0.0050 (12)
C9	0.083 (2)	0.0581 (17)	0.082 (2)	0.0115 (15)	0.0216 (16)	0.0202 (15)
C10	0.091 (2)	0.0580 (17)	0.081 (2)	−0.0034 (15)	0.0227 (17)	0.0049 (15)
C11	0.077 (2)	0.0677 (18)	0.073 (2)	−0.0105 (15)	0.0110 (15)	0.0068 (15)
C12	0.088 (2)	0.117 (3)	0.084 (2)	−0.001 (2)	0.0223 (19)	−0.006 (2)
N1	0.0607 (13)	0.0453 (11)	0.0558 (12)	−0.0063 (9)	0.0125 (10)	0.0013 (9)
O1	0.1261 (18)	0.0642 (12)	0.0553 (12)	0.0077 (11)	0.0326 (11)	0.0007 (10)
O2	0.0901 (14)	0.0549 (11)	0.0660 (12)	0.0015 (9)	0.0308 (10)	0.0019 (9)
S1	0.0605 (4)	0.0540 (4)	0.0910 (6)	−0.0155 (3)	0.0236 (4)	−0.0068 (4)
S2	0.0535 (4)	0.0570 (4)	0.0811 (5)	−0.0074 (3)	0.0092 (3)	0.0141 (3)

Geometric parameters (Å, º)

C1—N1	1.462 (3)	C7—C8	1.507 (4)
C1—C2	1.499 (4)	C7—S2	1.778 (3)
C1—H1A	0.9700	C7—H7A	0.9700
C1—H1B	0.9700	C7—H7B	0.9700
C2—C3	1.510 (4)	C8—O1	1.191 (3)
C2—H2A	0.9700	C8—O2	1.326 (3)
C2—H2B	0.9700	C9—O2	1.454 (3)
C3—C4	1.517 (4)	C9—C10	1.504 (4)
C3—H3A	0.9700	C9—H9A	0.9700
C3—H3B	0.9700	C9—H9B	0.9700
C4—C5	1.502 (4)	C10—C11	1.493 (4)
C4—H4A	0.9700	C10—H10A	0.9700
C4—H4B	0.9700	C10—H10B	0.9700
C5—N1	1.471 (3)	C11—C12	1.480 (4)
C5—H5A	0.9700	C11—H11A	0.9700
C5—H5B	0.9700	C11—H11B	0.9700
C6—N1	1.330 (3)	C12—H12A	0.9600
C6—S1	1.664 (2)	C12—H12B	0.9600
C6—S2	1.773 (3)	C12—H12C	0.9600
N1—C1—C2	109.1 (2)	C8—C7—H7B	108.4
N1—C1—H1A	109.9	S2—C7—H7B	108.4
C2—C1—H1A	109.9	H7A—C7—H7B	107.5
N1—C1—H1B	109.9	O1—C8—O2	125.4 (2)
C2—C1—H1B	109.9	O1—C8—C7	125.8 (2)
H1A—C1—H1B	108.3	O2—C8—C7	108.7 (2)
C1—C2—C3	111.7 (2)	O2—C9—C10	109.0 (2)
C1—C2—H2A	109.3	O2—C9—H9A	109.9
C3—C2—H2A	109.3	C10—C9—H9A	109.9
C1—C2—H2B	109.3	O2—C9—H9B	109.9
C3—C2—H2B	109.3	C10—C9—H9B	109.9
H2A—C2—H2B	107.9	H9A—C9—H9B	108.3
C2—C3—C4	110.7 (2)	C11—C10—C9	114.5 (3)
C2—C3—H3A	109.5	C11—C10—H10A	108.6
C4—C3—H3A	109.5	C9—C10—H10A	108.6
C2—C3—H3B	109.5	C11—C10—H10B	108.6
C4—C3—H3B	109.5	C9—C10—H10B	108.6
H3A—C3—H3B	108.1	H10A—C10—H10B	107.6
C5—C4—C3	110.6 (2)	C12—C11—C10	115.3 (3)
C5—C4—H4A	109.5	C12—C11—H11A	108.5
C3—C4—H4A	109.5	C10—C11—H11A	108.5
C5—C4—H4B	109.5	C12—C11—H11B	108.5
C3—C4—H4B	109.5	C10—C11—H11B	108.5
H4A—C4—H4B	108.1	H11A—C11—H11B	107.5
N1—C5—C4	109.7 (2)	C11—C12—H12A	109.5
N1—C5—H5A	109.7	C11—C12—H12B	109.5
C4—C5—H5A	109.7	H12A—C12—H12B	109.5
N1—C5—H5B	109.7	C11—C12—H12C	109.5
C4—C5—H5B	109.7	H12A—C12—H12C	109.5
H5A—C5—H5B	108.2	H12B—C12—H12C	109.5
N1—C6—S1	124.91 (19)	C6—N1—C1	122.6 (2)
N1—C6—S2	113.71 (17)	C6—N1—C5	124.7 (2)
S1—C6—S2	121.38 (14)	C1—N1—C5	111.2 (2)
C8—C7—S2	115.40 (19)	C8—O2—C9	118.9 (2)
C8—C7—H7A	108.4	C6—S2—C7	103.00 (12)
S2—C7—H7A	108.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···S1	0.97	2.59	3.080 (3)	112
C5—H5B···S2	0.97	2.38	2.914 (3)	114
C7—H7B···S1	0.97	2.62	3.056 (3)	108
C9—H9B···O1	0.97	2.32	2.735 (4)	105
C7—H7A···S1^i	0.97	2.95	3.823 (3)	151

Symmetry code: (i) x−1, y, z.