2-(Eth­oxy­carbono­thio­ylthio)­propanoic acid

In the title compound, C₆H₁₀O₃S₂, the O,S-diethyl carbonodi­thio­ate segment of the mol­ecule is almost planar and is inclined to the carb­oxy­lic acid substituent by 82.31 (8)°. In the crystal, O—H...O, C—H...O and C—H...S hydrogen bonds each form inversion dimers and combine with a short O...S contact of 3.2394 (16) Å to generate a three-dimensional network of mol­ecules stacked along all three axial directions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.047
• wR factor = 0.128
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     --  C1      ..        5.5 s.u.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  O1      ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A    ..  S1      ..       2.99 Ang.
PLAT975_ALERT_2_C Check Calcd Residual Density  0.90A From      O2       0.42 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          1 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3 Note
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..          9 % Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          7 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         21 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) and TITAN (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

2-(Ethoxycarbonothioylthio)propanoic acid

Crystal data

C6H10O3S2	Z = 2
Mr = 194.26	F(000) = 204
Triclinic, P1	Dx = 1.428 Mg m^−3
a = 7.4093 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 7.9779 (3) Å	Cell parameters from 4826 reflections
c = 8.6250 (3) Å	θ = 5.5–75.3°
α = 67.300 (4)°	µ = 5.04 mm^−1
β = 85.900 (4)°	T = 100 K
γ = 74.068 (4)°	Rectangular block, colourless
V = 451.93 (4) Å^3	0.30 × 0.13 × 0.10 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	1875 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1766 reflections with I > 2σ(I)
Detector resolution: 5.1725 pixels mm^-1	Rint = 0.064
ω scans	θmax = 76.3°, θmin = 5.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −9→9
Tmin = 0.637, Tmax = 1.000	k = −9→10
6643 measured reflections	l = −10→10

Refinement

Refinement on F^2	7 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0828P)^2 + 0.2987P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1875 reflections	Δρmax = 0.62 e Å^−3
115 parameters	Δρmin = −0.60 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.7282 (2)	0.4764 (2)	0.0116 (2)	0.0259 (4)
O2	0.4935 (2)	0.6981 (3)	0.0545 (2)	0.0272 (4)
H2O	0.433 (5)	0.647 (5)	0.042 (4)	0.041*
C1	0.6695 (3)	0.6171 (3)	0.0468 (3)	0.0201 (4)
C2	0.8089 (3)	0.7123 (3)	0.0736 (3)	0.0216 (5)
H2	0.9359	0.6201	0.0989	0.026*
C3	0.8165 (4)	0.8809 (4)	−0.0890 (3)	0.0305 (6)
H3A	0.8454	0.8383	−0.1827	0.046*
H3B	0.9143	0.9365	−0.0761	0.046*
H3C	0.6947	0.9756	−0.1122	0.046*
S2	0.7542 (6)	0.7994 (3)	0.24168 (12)	0.0156 (4)	0.861 (18)
S2A	0.704 (3)	0.829 (2)	0.2403 (9)	0.0171 (18)	0.139 (18)
C4	0.7572 (3)	0.5968 (3)	0.4189 (3)	0.0164 (4)
S1	0.75397 (7)	0.59867 (7)	0.60794 (6)	0.0198 (2)
O3	0.7618 (2)	0.4524 (2)	0.37763 (18)	0.0186 (3)
C5	0.7683 (3)	0.2696 (3)	0.5119 (3)	0.0210 (5)
H5A	0.6612	0.2809	0.5861	0.025*
H5B	0.8866	0.2208	0.5806	0.025*
C6	0.7573 (3)	0.1402 (3)	0.4260 (3)	0.0255 (5)
H6A	0.6388	0.1896	0.3598	0.038*
H6B	0.7633	0.0142	0.5108	0.038*
H6C	0.8628	0.1326	0.3514	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0334 (9)	0.0282 (10)	0.0246 (8)	−0.0125 (7)	−0.0001 (7)	−0.0159 (7)
O2	0.0306 (9)	0.0216 (9)	0.0329 (9)	−0.0108 (7)	−0.0083 (7)	−0.0100 (7)
C1	0.0253 (10)	0.0193 (11)	0.0158 (9)	−0.0089 (8)	−0.0033 (8)	−0.0041 (8)
C2	0.0251 (10)	0.0215 (11)	0.0206 (10)	−0.0084 (9)	−0.0035 (8)	−0.0083 (9)
C3	0.0420 (14)	0.0304 (14)	0.0237 (11)	−0.0202 (11)	−0.0006 (10)	−0.0078 (10)
S2	0.0174 (9)	0.0106 (5)	0.0188 (4)	−0.0019 (5)	−0.0058 (3)	−0.0058 (3)
S2A	0.019 (2)	0.018 (2)	0.0169 (19)	−0.0070 (11)	−0.0024 (9)	−0.0070 (11)
C4	0.0158 (8)	0.0147 (10)	0.0207 (9)	−0.0042 (7)	−0.0040 (7)	−0.0079 (8)
S1	0.0238 (3)	0.0186 (3)	0.0182 (3)	−0.0035 (2)	−0.0032 (2)	−0.0092 (2)
O3	0.0229 (7)	0.0147 (8)	0.0202 (7)	−0.0055 (6)	−0.0031 (6)	−0.0080 (6)
C5	0.0234 (10)	0.0144 (11)	0.0237 (10)	−0.0041 (8)	−0.0049 (8)	−0.0053 (8)
C6	0.0283 (11)	0.0153 (12)	0.0330 (12)	−0.0039 (9)	−0.0048 (9)	−0.0095 (9)

Geometric parameters (Å, º)

O1—C1	1.232 (3)	S2A—C4	1.856 (13)
O2—C1	1.296 (3)	C4—O3	1.322 (3)
O2—H2O	0.72 (4)	C4—S1	1.635 (2)
C1—C2	1.515 (3)	S1—O1^i	3.2394 (16)
C2—C3	1.535 (3)	O3—C5	1.462 (3)
C2—S2	1.813 (3)	C5—C6	1.505 (3)
C2—S2A	2.004 (13)	C5—H5A	0.9900
C2—H2	1.0000	C5—H5B	0.9900
C3—H3A	0.9800	C6—H6A	0.9800
C3—H3B	0.9800	C6—H6B	0.9800
C3—H3C	0.9800	C6—H6C	0.9800
S2—C4	1.740 (2)
C1—O2—H2O	112 (3)	O3—C4—S1	127.40 (17)
O1—C1—O2	124.6 (2)	O3—C4—S2	111.49 (15)
O1—C1—C2	118.99 (19)	S1—C4—S2	121.11 (13)
O2—C1—C2	116.27 (19)	O3—C4—S2A	114.6 (3)
C1—C2—C3	108.95 (18)	S1—C4—S2A	116.9 (3)
C1—C2—S2	114.60 (17)	C4—S1—O1^i	162.49 (9)
C3—C2—S2	107.51 (16)	C4—O3—C5	118.71 (16)
C1—C2—S2A	108.0 (4)	O3—C5—C6	106.08 (17)
C3—C2—S2A	104.2 (4)	O3—C5—H5A	110.5
C1—C2—H2	108.5	C6—C5—H5A	110.5
C3—C2—H2	108.5	O3—C5—H5B	110.5
S2—C2—H2	108.5	C6—C5—H5B	110.5
C2—C3—H3A	109.5	H5A—C5—H5B	108.7
C2—C3—H3B	109.5	C5—C6—H6A	109.5
H3A—C3—H3B	109.5	C5—C6—H6B	109.5
C2—C3—H3C	109.5	H6A—C6—H6B	109.5
H3A—C3—H3C	109.5	C5—C6—H6C	109.5
H3B—C3—H3C	109.5	H6A—C6—H6C	109.5
C4—S2—C2	103.40 (14)	H6B—C6—H6C	109.5
C4—S2A—C2	92.4 (7)
O1—C1—C2—C3	97.9 (2)	C2—S2A—C4—O3	−26.7 (7)
O2—C1—C2—C3	−78.7 (2)	C2—S2A—C4—S1	164.1 (2)
O1—C1—C2—S2	−141.7 (2)	O3—C4—S1—O1^i	−9.5 (4)
O2—C1—C2—S2	41.8 (3)	S2—C4—S1—O1^i	170.4 (2)
O1—C1—C2—S2A	−149.6 (5)	S2A—C4—S1—O1^i	158.1 (6)
O2—C1—C2—S2A	33.9 (5)	S1—C4—O3—C5	−1.2 (3)
C1—C2—S2—C4	60.7 (3)	S2—C4—O3—C5	178.92 (19)
C3—C2—S2—C4	−178.06 (19)	S2A—C4—O3—C5	−169.0 (6)
C2—S2—C4—O3	−11.7 (3)	C4—O3—C5—C6	175.74 (17)
C2—S2—C4—S1	168.43 (15)

Symmetry code: (i) x, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1^ii	0.72 (4)	1.92 (4)	2.639 (2)	175 (4)
C2—H2···O1^iii	1.00	2.62	3.497 (3)	146
C6—H6A···S1^iv	0.98	2.99	3.759 (2)	136

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