O-Butyl S-(1,1,3-trioxobenz[d]isothia­zol-2-yl)methyl dithiocarbonate

Akkurt, M.; Karaca, S.; Şahin, E.; Güzel, Ö.; Salman, A.

doi:10.1107/S160053680702363X

O-Butyl S-(1,1,3-trioxobenz[d]isothiazol-2-yl)methyl dithiocarbonate

M. Akkurt, S. Karaca, E. Şahin, Ö. Güzel and A. Salman

The asymmetric unit in the crystal structure of the title compound, C₁₃H₁₅NO₄S₃, comprises two molecules. Their nine-membered fused-ring systems are planar, with maximum deviations from the mean planes for the N atoms of 0.045 (3) and −0.028 (3) Å for the two molecules. The molecules are linked by intermolecular C—H

O hydrogen bonds oriented along the [010] axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702363X/kp2107sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680702363X/kp2107Isup2.hkl Contains datablock I

CCDC reference: 651484

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.007 Å
R factor = 0.076
wR factor = 0.197
Data-to-parameter ratio = 26.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O2'    ..  C7      ..       2.85 Ang.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.140
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.14
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C9'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C12'
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C7'     ..       2.99 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C13 H15 N O4 S3

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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

Comment top

Dithiocarbonate derivatives have been demonstrated to possess antifungal (Uchiyama & Hashimoto, 1974; Tsuchima & Wakamori, 1974) and antibacterial properties (Uchiyama & Hashimoto, 1974; Pennino, 1957). In our previous report (Güzel & Salman; 2006) the potent antimycobacterial and antitumor activities of the title compound were recorded. Here we report the crystal structure of the title compound which has potent antimycobacterial activity.

The asymmetric unit of the title compound (Fig. 1) reveals geometric parameters n agreement with the atom type and hybridization. The S═O and S═C distances are in the interval 1.418 (3) to 1.427 (3) and 1.612 (4) to 1.626 (5) Å, respectively. The O═S═O angles are 117.44 (17) ° for molecule A and 117.78 (17) ° for molecule B. The nine-membered fused rings of both molecules are planar; the maximum deviations from the mean planes are -0.038 (1) for S1, 0.045 (3) for N1 (ring A), and 0.016 (1) for S1', -0.028 (3) for N1' (ring B). In the asymmetric unit, the dihedral angle between the ring A and ring B of the two molecules is 3.76 (11)°. The crystal structure is stabilized by intermolecular C—H···O hydrogen bonds connecting molecules along the [010] axis (Table 2, Fig. 2).

Related literature top

For related literature, see: Güzel & Salman (2006); Pennino (1957); Tsuchima & Wakamori (1974); Uchiyama & Hashimoto (1974).

Experimental top

The ethanolic solution of 2-(chloromethyl)-1,2-benzisothiazol-3(2H)-on 1,1-dioxide and O-buthyldithiocarbonate (5 mmol) were refluxed for 1 h. After evaporation of the solvent in vacuo, products were washed with water and purified by recrystallization from ethanol. (Yield 42%, m.p. 325–327 K). IR (KBr): ν 1737 (C═O), 1246 (C═S). ¹H-NMR (DMSO-d₆/400 MHz): δ 0.92 (t, 3H, J=7.31 Hz, butyl CH₃), 1.39–1.48 (m, 2H, butyl C₃—H₂), 1.79–1.86 (m, 2H, butyl C₂—H₂), 4.65 (t, 2H, J=6.58 Hz, O—CH₂), 5.49 (s, 2H, N—CH₂—S), 7.99–8.14 (m, 3H, bzi, C_5,6,7—H), 8.33 (d, 1H, J=6.82 Hz, bzi, C₄—H). EIMS: m/z 345 (M⁺), Analysis calculated for C₁₃H₁₅NO₄S₃: C 45.20, H 4.38, N 4.05, S 27.85%. Found: C 45.49, H 3.98, N 4.07, S 27.55%.

Structure description top

For related literature, see: Güzel & Salman (2006); Pennino (1957); Tsuchima & Wakamori (1974); Uchiyama & Hashimoto (1974).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. Two independent molecules in the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of (I), showing hydrogen-bonding interactions (dashed lines). H atoms not involved in hydrogen contacts have been omitted.

O-Butyl S-(1,1,3-trioxobenz[d]isothiazol-2-yl)methyl dithiocarbonate top

Crystal data top

C₁₃H₁₅NO₄S₃	Z = 4
M_r = 345.47	F(000) = 720
Triclinic, P1	D_x = 1.393 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8191 (3) Å	Cell parameters from 5653 reflections
b = 13.4997 (2) Å	θ = 2.5–30.5°
c = 14.7531 (2) Å	µ = 0.46 mm⁻¹
α = 70.270 (3)°	T = 294 K
β = 85.255 (5)°	Block, light yellow
γ = 89.696 (5)°	0.20 × 0.20 × 0.20 mm
V = 1647.18 (7) Å³

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	9889 independent reflections
Radiation source: fine-focus sealed tube	3931 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.140
ω scans	θ_max = 30.6°, θ_min = 2.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −12→11
T_min = 0.913, T_max = 0.913	k = −19→19
46335 measured reflections	l = −21→21

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0565P)²] where P = (F_o² + 2F_c²)/3
9889 reflections	(Δ/σ)_max = 0.001
381 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₃H₁₅NO₄S₃	γ = 89.696 (5)°
M_r = 345.47	V = 1647.18 (7) Å³
Triclinic, P1	Z = 4
a = 8.8191 (3) Å	Mo Kα radiation
b = 13.4997 (2) Å	µ = 0.46 mm⁻¹
c = 14.7531 (2) Å	T = 294 K
α = 70.270 (3)°	0.20 × 0.20 × 0.20 mm
β = 85.255 (5)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	9889 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3931 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.913	R_int = 0.140
46335 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 1.01	Δρ_max = 0.25 e Å⁻³
9889 reflections	Δρ_min = −0.26 e Å⁻³
381 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
S1	1.06266 (10)	0.29619 (7)	0.05807 (7)	0.0681 (3)
S2	1.10307 (13)	0.00305 (8)	0.21582 (9)	0.0905 (4)
S3	1.21346 (16)	0.02860 (12)	0.38646 (10)	0.1256 (6)
O1	1.1357 (3)	0.30388 (19)	0.13759 (18)	0.0785 (10)
O2	0.9098 (3)	0.3310 (2)	0.0490 (2)	0.0898 (10)
O3	1.1811 (3)	0.07802 (19)	−0.03274 (19)	0.0787 (10)
O4	0.9792 (3)	0.1259 (2)	0.2981 (2)	0.0916 (11)
N1	1.0696 (3)	0.1740 (2)	0.0554 (2)	0.0649 (10)
C1	1.2230 (4)	0.2660 (3)	−0.0846 (3)	0.0625 (11)
C2	1.3151 (4)	0.2870 (3)	−0.1690 (3)	0.0769 (16)
C3	1.3590 (5)	0.3907 (4)	−0.2192 (3)	0.0915 (19)
C4	1.3136 (5)	0.4693 (4)	−0.1849 (4)	0.0953 (19)
C5	1.2219 (5)	0.4497 (3)	−0.0991 (3)	0.0839 (16)
C6	1.1782 (4)	0.3466 (3)	−0.0507 (3)	0.0636 (12)
C7	1.1599 (4)	0.1622 (3)	−0.0222 (3)	0.0645 (11)
C8	0.9852 (4)	0.0846 (3)	0.1246 (3)	0.0796 (16)
C9	1.0928 (4)	0.0605 (3)	0.3056 (3)	0.0815 (16)
C10	0.9636 (6)	0.1863 (4)	0.3638 (3)	0.114 (2)
C11	0.8268 (7)	0.2521 (4)	0.3395 (4)	0.124 (3)
C12	0.6805 (8)	0.1885 (5)	0.3673 (5)	0.158 (3)
C13	0.5369 (8)	0.2503 (5)	0.3586 (5)	0.158 (3)
S1'	0.75578 (10)	0.25022 (7)	−0.14738 (7)	0.0685 (3)
S2'	0.75963 (14)	0.51558 (9)	−0.34352 (9)	0.1022 (5)
S3'	0.7432 (2)	0.44961 (13)	−0.51090 (11)	0.1369 (7)
O1'	0.6760 (3)	0.2329 (2)	−0.22091 (18)	0.0829 (11)
O2'	0.9079 (2)	0.2140 (2)	−0.13762 (19)	0.0817 (10)
O3'	0.6476 (3)	0.48732 (19)	−0.0829 (2)	0.0874 (10)
O4'	0.9228 (3)	0.3687 (2)	−0.3707 (2)	0.0916 (11)
N1'	0.7536 (3)	0.3769 (2)	−0.1574 (2)	0.0716 (11)
C1'	0.5993 (4)	0.3005 (3)	−0.0145 (3)	0.0616 (11)
C2'	0.5069 (4)	0.2884 (3)	0.0699 (3)	0.0714 (16)
C3'	0.4636 (4)	0.1873 (3)	0.1290 (3)	0.0826 (16)
C4'	0.5106 (5)	0.1009 (3)	0.1041 (3)	0.0879 (17)
C5'	0.6011 (4)	0.1122 (3)	0.0209 (3)	0.0751 (14)
C6'	0.6423 (3)	0.2133 (3)	−0.0375 (3)	0.0637 (11)
C7'	0.6624 (4)	0.3993 (3)	−0.0845 (3)	0.0664 (14)
C8'	0.8445 (5)	0.4588 (3)	−0.2321 (3)	0.0874 (17)
C9'	0.8184 (5)	0.4344 (4)	−0.4102 (3)	0.0920 (17)
C10'	0.9840 (5)	0.2953 (4)	−0.4172 (3)	0.0928 (17)
C11'	1.1245 (5)	0.2504 (3)	−0.3682 (3)	0.0890 (17)
C12'	1.2043 (6)	0.1771 (4)	−0.4132 (3)	0.1050 (19)
C13'	1.3434 (7)	0.1294 (5)	−0.3628 (5)	0.152 (3)
H2	1.34690	0.23330	−0.19180	0.0920*
H3	1.42020	0.40700	−0.27700	0.1100*
H4	1.34510	0.53820	−0.22010	0.1150*
H5	1.19180	0.50340	−0.07580	0.1010*
H8A	0.94410	0.04200	0.09050	0.0950*
H8B	0.90040	0.10980	0.15630	0.0950*
H10C	1.05350	0.23060	0.35560	0.1360*
H10D	0.95110	0.13930	0.43030	0.1360*
H11C	0.83450	0.29040	0.27060	0.1490*
H11D	0.82490	0.30330	0.37250	0.1490*
H12C	0.68160	0.14200	0.43380	0.1900*
H12D	0.67730	0.14460	0.32720	0.1900*
H13D	0.53590	0.29190	0.40020	0.2380*
H13E	0.45040	0.20280	0.37720	0.2380*
H13F	0.53280	0.29580	0.29290	0.2380*
H8'1	0.94100	0.42950	−0.24530	0.1040*
H2'	0.47520	0.34650	0.08610	0.0860*
H8'2	0.86600	0.51460	−0.20690	0.1040*
H3'	0.40240	0.17710	0.18590	0.0990*
H4'	0.48000	0.03380	0.14480	0.1050*
H5'	0.63320	0.05410	0.00460	0.0900*
H10A	1.00950	0.33160	−0.48570	0.1110*
H10B	0.90990	0.23960	−0.40950	0.1110*
H11A	1.09620	0.21250	−0.30040	0.1070*
H11B	1.19390	0.30760	−0.37250	0.1070*
H12A	1.23470	0.21560	−0.48070	0.1260*
H12B	1.13390	0.12100	−0.41050	0.1260*
H13A	1.41410	0.18460	−0.36590	0.2270*
H13B	1.39080	0.08390	−0.39410	0.2270*
H13C	1.31350	0.08950	−0.29640	0.2270*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0650 (5)	0.0658 (5)	0.0878 (7)	0.0081 (4)	−0.0113 (5)	−0.0436 (5)
S2	0.1002 (8)	0.0636 (6)	0.1003 (8)	0.0047 (5)	0.0069 (6)	−0.0218 (6)
S3	0.1183 (11)	0.1404 (12)	0.1018 (10)	0.0155 (9)	−0.0289 (8)	−0.0153 (8)
O1	0.0813 (16)	0.0878 (17)	0.0841 (17)	−0.0013 (13)	−0.0138 (13)	−0.0508 (14)
O2	0.0624 (15)	0.0969 (19)	0.134 (2)	0.0229 (13)	−0.0190 (15)	−0.0680 (17)
O3	0.0814 (16)	0.0639 (15)	0.105 (2)	0.0118 (12)	−0.0122 (14)	−0.0465 (14)
O4	0.106 (2)	0.0890 (19)	0.088 (2)	0.0145 (16)	−0.0172 (16)	−0.0388 (16)
N1	0.0719 (18)	0.0572 (16)	0.0748 (19)	0.0004 (13)	−0.0044 (15)	−0.0347 (14)
C1	0.0578 (19)	0.064 (2)	0.074 (2)	0.0103 (16)	−0.0182 (17)	−0.0313 (18)
C2	0.069 (2)	0.092 (3)	0.076 (3)	0.013 (2)	−0.014 (2)	−0.035 (2)
C3	0.083 (3)	0.106 (4)	0.078 (3)	0.001 (3)	−0.013 (2)	−0.020 (3)
C4	0.095 (3)	0.077 (3)	0.100 (4)	0.000 (2)	−0.016 (3)	−0.010 (3)
C5	0.092 (3)	0.059 (2)	0.106 (3)	0.008 (2)	−0.022 (3)	−0.032 (2)
C6	0.063 (2)	0.059 (2)	0.073 (2)	0.0090 (16)	−0.0156 (17)	−0.0255 (17)
C7	0.0581 (19)	0.062 (2)	0.083 (2)	0.0110 (16)	−0.0159 (17)	−0.0350 (19)
C8	0.081 (2)	0.079 (3)	0.093 (3)	−0.012 (2)	−0.005 (2)	−0.048 (2)
C9	0.081 (3)	0.065 (2)	0.086 (3)	−0.001 (2)	−0.003 (2)	−0.010 (2)
C10	0.141 (4)	0.125 (4)	0.092 (3)	0.016 (3)	−0.015 (3)	−0.058 (3)
C11	0.157 (5)	0.118 (4)	0.117 (4)	0.023 (4)	−0.003 (4)	−0.068 (3)
C12	0.136 (5)	0.143 (6)	0.193 (7)	0.016 (5)	−0.003 (5)	−0.056 (5)
C13	0.154 (6)	0.152 (6)	0.172 (6)	−0.007 (5)	0.011 (5)	−0.064 (5)
S1'	0.0633 (5)	0.0718 (6)	0.0844 (7)	0.0121 (4)	−0.0105 (5)	−0.0440 (5)
S2'	0.1055 (9)	0.0873 (8)	0.0985 (9)	0.0133 (6)	0.0081 (7)	−0.0157 (6)
S3'	0.1587 (14)	0.1380 (13)	0.1141 (11)	0.0267 (10)	−0.0501 (10)	−0.0343 (9)
O1'	0.0811 (17)	0.0959 (19)	0.0939 (19)	0.0168 (14)	−0.0224 (14)	−0.0581 (16)
O2'	0.0603 (15)	0.0977 (19)	0.0991 (19)	0.0198 (13)	−0.0098 (13)	−0.0484 (15)
O3'	0.0924 (18)	0.0676 (16)	0.115 (2)	0.0044 (13)	0.0048 (15)	−0.0507 (15)
O4'	0.0881 (19)	0.104 (2)	0.0826 (19)	0.0140 (16)	−0.0060 (15)	−0.0321 (16)
N1'	0.0783 (19)	0.0649 (18)	0.079 (2)	0.0053 (15)	0.0022 (16)	−0.0362 (16)
C1'	0.0553 (18)	0.062 (2)	0.077 (2)	0.0095 (15)	−0.0122 (17)	−0.0347 (18)
C2'	0.064 (2)	0.080 (3)	0.083 (3)	0.0117 (18)	−0.0121 (19)	−0.043 (2)
C3'	0.072 (2)	0.094 (3)	0.082 (3)	0.006 (2)	−0.011 (2)	−0.029 (2)
C4'	0.075 (3)	0.074 (3)	0.107 (3)	0.008 (2)	−0.010 (2)	−0.020 (2)
C5'	0.062 (2)	0.062 (2)	0.108 (3)	0.0114 (17)	−0.015 (2)	−0.036 (2)
C6'	0.0529 (18)	0.064 (2)	0.083 (2)	0.0105 (15)	−0.0139 (17)	−0.0348 (19)
C7'	0.059 (2)	0.070 (2)	0.081 (3)	0.0091 (17)	−0.0087 (17)	−0.039 (2)
C8'	0.093 (3)	0.081 (3)	0.093 (3)	−0.012 (2)	0.016 (2)	−0.041 (2)
C9'	0.091 (3)	0.087 (3)	0.091 (3)	−0.006 (2)	0.001 (2)	−0.023 (2)
C10'	0.102 (3)	0.102 (3)	0.082 (3)	0.001 (3)	0.000 (2)	−0.043 (2)
C11'	0.094 (3)	0.084 (3)	0.090 (3)	0.000 (2)	0.002 (2)	−0.033 (2)
C12'	0.120 (4)	0.100 (3)	0.099 (3)	0.003 (3)	0.012 (3)	−0.044 (3)
C13'	0.143 (5)	0.159 (5)	0.176 (6)	0.062 (4)	−0.026 (4)	−0.085 (5)

Geometric parameters (Å, º) top

S1—O1	1.418 (3)	C5—H5	0.9300
S1—O2	1.427 (3)	C8—H8B	0.9700
S1—N1	1.664 (3)	C8—H8A	0.9700
S1—C6	1.754 (4)	C10—H10C	0.9700
S2—C8	1.823 (4)	C10—H10D	0.9700
S2—C9	1.743 (5)	C11—H11C	0.9700
S3—C9	1.612 (4)	C11—H11D	0.9700
S1'—O2'	1.427 (2)	C12—H12D	0.9700
S1'—N1'	1.666 (3)	C12—H12C	0.9700
S1'—C6'	1.752 (4)	C13—H13E	0.9600
S1'—O1'	1.423 (3)	C13—H13F	0.9600
S2'—C8'	1.788 (5)	C13—H13D	0.9600
S2'—C9'	1.754 (5)	C1'—C2'	1.392 (6)
S3'—C9'	1.626 (5)	C1'—C6'	1.374 (6)
O3—C7	1.210 (5)	C1'—C7'	1.462 (6)
O4—C9	1.319 (5)	C2'—C3'	1.384 (6)
O4—C10	1.461 (6)	C3'—C4'	1.388 (6)
O3'—C7'	1.203 (5)	C4'—C5'	1.371 (6)
O4'—C9'	1.306 (6)	C5'—C6'	1.377 (6)
O4'—C10'	1.461 (6)	C10'—C11'	1.507 (6)
N1—C8	1.451 (5)	C11'—C12'	1.508 (7)
N1—C7	1.393 (5)	C12'—C13'	1.514 (8)
N1'—C8'	1.456 (5)	C2'—H2'	0.9300
N1'—C7'	1.403 (5)	C3'—H3'	0.9300
C1—C2	1.374 (6)	C4'—H4'	0.9300
C1—C6	1.386 (6)	C5'—H5'	0.9300
C1—C7	1.474 (6)	C8'—H8'1	0.9700
C2—C3	1.384 (7)	C8'—H8'2	0.9700
C3—C4	1.366 (8)	C10'—H10A	0.9700
C4—C5	1.390 (7)	C10'—H10B	0.9700
C5—C6	1.373 (6)	C11'—H11A	0.9700
C10—C11	1.489 (8)	C11'—H11B	0.9700
C11—C12	1.502 (9)	C12'—H12A	0.9700
C12—C13	1.503 (10)	C12'—H12B	0.9700
C2—H2	0.9300	C13'—H13A	0.9600
C3—H3	0.9300	C13'—H13B	0.9600
C4—H4	0.9300	C13'—H13C	0.9600

S1'···O4'	3.354 (3)	C2'···O1^vi	3.369 (5)
S2···O2'ⁱ	3.497 (4)	C2'···C6^vi	3.474 (6)
S2···O3	3.468 (4)	C3···C7'ⁱⁱ	3.487 (6)
S3···H10C	2.9800	C3'···O1^vi	3.299 (5)
S3···H13Eⁱⁱ	3.1200	C4···C7'ⁱⁱ	3.511 (6)
S3···H10Dⁱⁱⁱ	3.1300	C5···O3'^viii	3.365 (5)
S3···H12Cⁱⁱⁱ	3.0700	C5'···O3ⁱ	3.165 (5)
S3···H10D	2.8900	C6···C2'ⁱⁱ	3.474 (6)
S3'···H11D^iv	3.0700	C6'···O2	3.410 (5)
S3'···H10B	3.1500	C6'···C2^vi	3.560 (5)
S3'···H11B^v	3.1700	C7···O2'	2.852 (5)
S3'···H10A	2.8100	C7'···C3^vi	3.487 (6)
O1···C3'ⁱⁱ	3.299 (5)	C7'···C4^vi	3.511 (6)
O1···C9	3.383 (5)	C7'···O2	2.992 (5)
O1···C10	3.402 (5)	C8···O3ⁱ	3.344 (5)
O1···C2'ⁱⁱ	3.369 (5)	C9···O1	3.383 (5)
O1···O4	2.990 (4)	C9'···O1'	3.332 (6)
O1'···C9'	3.332 (6)	C10···O1	3.402 (5)
O1'···O4'	3.081 (4)	C9···H12Bⁱ	3.0600
O1'···C2^vi	3.347 (5)	C13···H4^viii	3.0300
O2···C1'	3.040 (5)	H8'1···O4'	2.2800
O2···C6'	3.410 (5)	H8'1···O2'	2.8100
O2···C7'	2.992 (5)	H2···O1'ⁱⁱ	2.9000
O2'···C7	2.852 (5)	H2···O3	2.8600
O2'···C1	3.095 (5)	H2'···O3'	2.8900
O2'···S2ⁱ	3.497 (4)	H2'···O3'^vii	2.4700
O2'···O3	3.197 (4)	H8'2···O3'	2.4800
O2'···N1	3.172 (4)	H3'···O1^vi	2.8900
O3···O2'	3.197 (4)	H4···H13F^viii	2.3500
O3···S2	3.468 (4)	H4···C13^viii	3.0300
O3···C8ⁱ	3.344 (5)	H5···O2^viii	2.5400
O3···C5'ⁱ	3.165 (5)	H5···O3'^viii	2.8700
O3'···C2'^vii	3.371 (5)	H5'···O3ⁱ	2.3700
O3'···C5^viii	3.365 (5)	H8A···O3	2.5900
O4···O1	2.990 (4)	H8A···O3ⁱ	2.3800
O4'···S1'	3.354 (3)	H8B···O4	2.3400
O4'···O1'	3.081 (4)	H8B···O2	2.8700
O1···H3'ⁱⁱ	2.8900	H10A···S3'	2.8100
O1'···H2^vi	2.9000	H10A···H12A	2.5100
O2···H5^viii	2.5400	H10B···H12B	2.5400
O2···H8B	2.8700	H10B···S3'	3.1500
O2'···H8'1	2.8100	H10C···S3	2.9800
O2'···H11A	2.8100	H10D···S3	2.8900
O3···H2	2.8600	H10D···H12C	2.3700
O3···H5'ⁱ	2.3700	H10D···S3ⁱⁱⁱ	3.1300
O3···H8A	2.5900	H11A···O2'	2.8100
O3···H8Aⁱ	2.3800	H11A···H13C	2.5200
O3'···H8'2	2.4800	H11B···S3'^v	3.1700
O3'···H2'^vii	2.4700	H11B···H13A	2.5300
O3'···H5^viii	2.8700	H11D···S3'^ix	3.0700
O3'···H2'	2.8900	H11D···H13D	2.5400
O4···H8B	2.3400	H12A···H10A	2.5100
O4···H12D	2.6900	H12B···H10B	2.5400
O4'···H8'1	2.2800	H12B···C9ⁱ	3.0600
N1···O2'	3.172 (4)	H12C···H10D	2.3700
C1···O2'	3.095 (5)	H12C···S3ⁱⁱⁱ	3.0700
C1'···C2^vi	3.569 (6)	H12D···O4	2.6900
C1'···O2	3.040 (5)	H13A···H11B	2.5300
C2···C6'ⁱⁱ	3.560 (5)	H13C···H11A	2.5200
C2···C1'ⁱⁱ	3.569 (6)	H13D···H11D	2.5400
C2···O1'ⁱⁱ	3.347 (5)	H13E···S3^vi	3.1200
C2'···O3'^vii	3.371 (5)	H13F···H4^viii	2.3500

O1—S1—O2	117.44 (17)	C11—C12—H12C	108.00
O1—S1—N1	110.72 (16)	C11—C12—H12D	108.00
O1—S1—C6	111.87 (17)	C13—C12—H12C	108.00
O2—S1—N1	108.88 (16)	C13—C12—H12D	108.00
O2—S1—C6	112.53 (18)	H12C—C12—H12D	107.00
N1—S1—C6	92.60 (18)	C12—C13—H13F	109.00
C8—S2—C9	104.7 (2)	H13E—C13—H13F	110.00
N1'—S1'—C6'	92.19 (18)	H13D—C13—H13E	109.00
O2'—S1'—C6'	113.33 (16)	H13D—C13—H13F	109.00
O1'—S1'—O2'	117.78 (17)	C12—C13—H13D	109.00
O1'—S1'—N1'	110.66 (16)	C12—C13—H13E	109.00
O1'—S1'—C6'	110.78 (16)	C2'—C1'—C6'	119.7 (4)
O2'—S1'—N1'	109.15 (15)	C2'—C1'—C7'	126.8 (4)
C8'—S2'—C9'	103.6 (2)	C6'—C1'—C7'	113.5 (4)
C9—O4—C10	118.7 (3)	C1'—C2'—C3'	118.1 (4)
C9'—O4'—C10'	120.0 (3)	C2'—C3'—C4'	120.7 (4)
S1—N1—C8	124.5 (2)	C3'—C4'—C5'	121.6 (4)
C7—N1—C8	120.5 (3)	C4'—C5'—C6'	117.0 (4)
S1—N1—C7	115.0 (3)	S1'—C6'—C1'	110.6 (3)
C7'—N1'—C8'	121.4 (3)	S1'—C6'—C5'	126.6 (3)
S1'—N1'—C7'	114.8 (2)	C1'—C6'—C5'	122.9 (4)
S1'—N1'—C8'	123.7 (2)	O3'—C7'—N1'	122.4 (4)
C2—C1—C7	126.6 (4)	O3'—C7'—C1'	128.7 (4)
C2—C1—C6	120.5 (4)	N1'—C7'—C1'	108.8 (3)
C6—C1—C7	112.9 (4)	S2'—C8'—N1'	115.4 (3)
C1—C2—C3	117.9 (4)	S2'—C9'—S3'	118.7 (3)
C2—C3—C4	120.8 (4)	S2'—C9'—O4'	113.1 (3)
C3—C4—C5	122.2 (5)	S3'—C9'—O4'	128.2 (4)
C4—C5—C6	116.2 (4)	O4'—C10'—C11'	106.5 (3)
S1—C6—C1	110.2 (3)	C10'—C11'—C12'	112.0 (4)
S1—C6—C5	127.5 (3)	C11'—C12'—C13'	112.4 (4)
C1—C6—C5	122.3 (4)	C1'—C2'—H2'	121.00
O3—C7—C1	127.7 (4)	C3'—C2'—H2'	121.00
O3—C7—N1	123.2 (4)	C2'—C3'—H3'	120.00
N1—C7—C1	109.2 (3)	C4'—C3'—H3'	120.00
S2—C8—N1	112.3 (2)	C3'—C4'—H4'	119.00
S2—C9—S3	119.5 (2)	C5'—C4'—H4'	119.00
S2—C9—O4	112.6 (3)	C4'—C5'—H5'	121.00
S3—C9—O4	128.0 (3)	C6'—C5'—H5'	122.00
O4—C10—C11	107.0 (4)	S2'—C8'—H8'1	108.00
C10—C11—C12	112.9 (5)	S2'—C8'—H8'2	108.00
C11—C12—C13	116.0 (6)	N1'—C8'—H8'1	108.00
C3—C2—H2	121.00	N1'—C8'—H8'2	108.00
C1—C2—H2	121.00	H8'1—C8'—H8'2	107.00
C2—C3—H3	120.00	O4'—C10'—H10A	110.00
C4—C3—H3	120.00	O4'—C10'—H10B	110.00
C5—C4—H4	119.00	C11'—C10'—H10A	110.00
C3—C4—H4	119.00	C11'—C10'—H10B	110.00
C4—C5—H5	122.00	H10A—C10'—H10B	109.00
C6—C5—H5	122.00	C10'—C11'—H11A	109.00
S2—C8—H8B	109.00	C10'—C11'—H11B	109.00
S2—C8—H8A	109.00	C12'—C11'—H11A	109.00
H8A—C8—H8B	108.00	C12'—C11'—H11B	109.00
N1—C8—H8A	109.00	H11A—C11'—H11B	108.00
N1—C8—H8B	109.00	C11'—C12'—H12A	109.00
C11—C10—H10C	110.00	C11'—C12'—H12B	109.00
O4—C10—H10D	110.00	C13'—C12'—H12A	109.00
C11—C10—H10D	110.00	C13'—C12'—H12B	109.00
H10C—C10—H10D	109.00	H12A—C12'—H12B	108.00
O4—C10—H10C	110.00	C12'—C13'—H13A	109.00
C10—C11—H11C	109.00	C12'—C13'—H13B	109.00
H11C—C11—H11D	108.00	C12'—C13'—H13C	109.00
C10—C11—H11D	109.00	H13A—C13'—H13B	110.00
C12—C11—H11C	109.00	H13A—C13'—H13C	109.00
C12—C11—H11D	109.00	H13B—C13'—H13C	109.00

O1—S1—N1—C7	−112.4 (3)	S1—N1—C7—C1	−1.8 (4)
O1—S1—N1—C8	70.1 (3)	S1'—N1'—C8'—S2'	86.8 (3)
O2—S1—N1—C7	117.1 (3)	S1'—N1'—C7'—O3'	−178.8 (3)
O2—S1—N1—C8	−60.5 (3)	S1'—N1'—C7'—C1'	3.3 (4)
C6—S1—N1—C7	2.2 (3)	C8'—N1'—C7'—O3'	4.4 (5)
C6—S1—N1—C8	−175.3 (3)	C8'—N1'—C7'—C1'	−173.5 (3)
O1—S1—C6—C1	111.7 (3)	C7'—N1'—C8'—S2'	−96.6 (4)
O1—S1—C6—C5	−68.4 (4)	C6—C1—C2—C3	−1.0 (6)
O2—S1—C6—C1	−113.6 (3)	C6—C1—C7—N1	0.3 (4)
O2—S1—C6—C5	66.3 (4)	C2—C1—C6—S1	−179.7 (3)
N1—S1—C6—C1	−1.9 (3)	C2—C1—C6—C5	0.4 (6)
N1—S1—C6—C5	178.0 (4)	C7—C1—C6—S1	1.2 (4)
C9—S2—C8—N1	86.9 (3)	C7—C1—C6—C5	−178.7 (4)
C8—S2—C9—S3	−165.2 (3)	C2—C1—C7—O3	2.2 (7)
C8—S2—C9—O4	16.1 (3)	C2—C1—C7—N1	−178.7 (4)
C6'—S1'—N1'—C8'	172.9 (3)	C7—C1—C2—C3	178.0 (4)
O1'—S1'—C6'—C1'	−109.8 (3)	C6—C1—C7—O3	−178.8 (4)
O1'—S1'—C6'—C5'	71.2 (3)	C1—C2—C3—C4	0.9 (6)
O2'—S1'—C6'—C1'	115.2 (3)	C2—C3—C4—C5	−0.2 (7)
O2'—S1'—C6'—C5'	−63.7 (4)	C3—C4—C5—C6	−0.5 (7)
N1'—S1'—C6'—C1'	3.3 (3)	C4—C5—C6—S1	−179.5 (3)
N1'—S1'—C6'—C5'	−175.7 (3)	C4—C5—C6—C1	0.3 (6)
O2'—S1'—N1'—C8'	57.3 (3)	O4—C10—C11—C12	70.2 (5)
C6'—S1'—N1'—C7'	−3.8 (3)	C10—C11—C12—C13	171.3 (5)
O1'—S1'—N1'—C8'	−73.9 (3)	C6'—C1'—C2'—C3'	1.1 (5)
O2'—S1'—N1'—C7'	−119.5 (3)	C7'—C1'—C2'—C3'	−177.4 (4)
O1'—S1'—N1'—C7'	109.4 (3)	C2'—C1'—C6'—S1'	179.3 (3)
C8'—S2'—C9'—O4'	−10.3 (4)	C2'—C1'—C6'—C5'	−1.7 (5)
C9'—S2'—C8'—N1'	−88.9 (3)	C7'—C1'—C6'—S1'	−2.0 (4)
C8'—S2'—C9'—S3'	170.8 (3)	C7'—C1'—C6'—C5'	177.0 (3)
C10—O4—C9—S3	6.2 (6)	C2'—C1'—C7'—O3'	0.2 (7)
C10—O4—C9—S2	−175.2 (3)	C2'—C1'—C7'—N1'	177.9 (4)
C9—O4—C10—C11	−179.7 (4)	C6'—C1'—C7'—O3'	−178.4 (4)
C10'—O4'—C9'—S2'	179.9 (3)	C6'—C1'—C7'—N1'	−0.7 (4)
C10'—O4'—C9'—S3'	−1.3 (6)	C1'—C2'—C3'—C4'	−0.4 (6)
C9'—O4'—C10'—C11'	166.8 (4)	C2'—C3'—C4'—C5'	0.1 (6)
C8—N1—C7—O3	−5.0 (5)	C3'—C4'—C5'—C6'	−0.6 (6)
C8—N1—C7—C1	175.8 (3)	C4'—C5'—C6'—S1'	−179.8 (3)
S1—N1—C8—S2	−100.8 (3)	C4'—C5'—C6'—C1'	1.4 (5)
C7—N1—C8—S2	81.8 (4)	O4'—C10'—C11'—C12'	−177.0 (3)
S1—N1—C7—O3	177.3 (3)	C10'—C11'—C12'—C13'	−178.5 (4)

Symmetry codes: (i) −x+2, −y, −z; (ii) x+1, y, z; (iii) −x+2, −y, −z+1; (iv) x, y, z−1; (v) −x+2, −y+1, −z−1; (vi) x−1, y, z; (vii) −x+1, −y+1, −z; (viii) −x+2, −y+1, −z; (ix) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2′—H2′···O3′^vii	0.93	2.47	3.371 (5)	162
C8′—H8′2···O3′	0.97	2.48	2.818 (5)	100
C5—H5···O2^viii	0.93	2.54	3.458 (6)	167
C5′—H5′···O3ⁱ	0.93	2.37	3.165 (5)	143
C8—H8A···O3ⁱ	0.97	2.38	3.344 (5)	170

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₅NO₄S₃
M_r	345.47
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.8191 (3), 13.4997 (2), 14.7531 (2)
α, β, γ (°)	70.270 (3), 85.255 (5), 89.696 (5)
V (Å³)	1647.18 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.913, 0.913
No. of measured, independent and observed [I > 2σ(I)] reflections	46335, 9889, 3931
R_int	0.140
(sin θ/λ)_max (Å⁻¹)	0.716

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.197, 1.01
No. of reflections	9889
No. of parameters	381
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.26

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2003).