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rac-2-Isopropyl-3-(2-nitro­benz­yl)-1,3-thia­diazo­lin-4-one, C13H16N2O3S, is a rare example of a racemate crystallizing in the space group P212121, with one mol­ecule each of S and R configurations, whose conformations are almost mirror images, within the asymmetric unit. The mol­ecules of S configuration are linked by two C-H...O hydrogen bonds into a three-dimensional framework, and the mol­ecules of R configuration are linked by two further C-H...O hydrogen bonds into a different type of three-dimensional framework; the two frameworks are linked by a fifth C-H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107022913/sk3126sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107022913/sk3126Isup2.hkl
Contains datablock I

CCDC reference: 655510

Comment top

Thiazolidinones and their derivatives are an important group of heterocyclic compounds having valuable biological activities in the areas of medicine and agriculture (Singh et al., 1981). We report here the molecular and supramolecular structure of the title compound, (I), which was obtained from the reaction between 2-amino-3-methylbutanoic acid (valine), 2-nitrobenzaldehyde and mercaptoacetic acid; a mechanism for this reaction has recently been proposed (Cunico et al., 2007).

Compound (I) crystallizes with Z' = 2 in space group P212121. The two independent molecules, denoted A and B (Fig. 1), have S and R configurations, respectively, at atom C2. Hence, (I) is a racemate with a chiral crystal structure (Flack, 2003). A recent study (Dalhus & Görbitz, 2000), based on the Cambridge Structural Database (Allen, 2002), of racemates crystallizing in noncentrosymmetric space groups found that these nearly always crystallize in space groups containing glide planes. Five space groups (Pc, Cc, Pca21, Pna21 and Fdd2) account for over 90% of all such racemates. By contrast, genuine racemates that crystallize in space groups having no symmetry operators of the second kind (inversion, reflection or roto-inversion) were found to be extremely rare with only 17 authentic examples, distributed amongst the space groups P1 (only one example identified), P21 (11 examples identified), P212121 (four examples identified) and P3121 (one example identified) (Dalhus & Görbitz, 2000). Compound (I) is thus an addition to this very rare class of crystalline racemates.

The two independent molecules in compound (I) are, in fact, almost enantiomeric, as shown by the leading torsion angles (Table 1) and by the puckering parameters for the heterocyclic rings. For racemates crystallizing in noncentrosymmetric space groups and having Z' > 1, it was found (Dalhus & Görbitz, 2000) that the independent molecules, in general, adopt closely similar conformations, as observed here for compound (I).

The values of the ring-puckering parameter ϕ for the atom sequence S1—C2—N3—C4—C5 are 177.1 (6)° for molecule A and 359.8 (6)° for molecule B, while the values of ϕ for true enantiomers differ by exactly 180°. In each independent molecule in (I), the heterocyclic ring thus adopts an envelope conformation, for which the ideal value of ϕ is (36n)°, where n is zero or an integer, and each ring is folded across the line C2···C5. However, there is no additional crystallographic symmetry and the differences between the hydrogen bonds formed by the two independent molecules (Table 2) are sufficient to preclude any such additional symmetry.

The hydrogen-bonded supramolecular structure is three-dimensional and it is convenient to consider in turn the supramolecular aggregation of the type A and B molecules. Atoms C2A and C34A in the type A molecule at (x, y, z) act, respectively, as hydrogen-bond donors to atoms O4A and O31A in the type A molecules at (1/2 + x, 1/2 - y, -z) and (3/2 - x, -y, -1/2 + z). Propagation of each of these interactions alone produces a C(5) (Bernstein et al., 1995) chain running parallel to the [100] direction and generated by the 21 screw axis along (x, 1/4, 0), and a C(6) chain running parallel to [001] and generated by the screw axis along (3/4, 0, z). The combination of these two hydrogen bonds generates a C22(17) chain running parallel to the [010] direction (Fig. 2) and the combination of chains along [100], [010] and [001] suffices to generate a three-dimensional framework built solely from type A molecules, all of S configuration.

A second three-dimensional framework is formed by the type B molecules. The atoms C2B and C35B in the type B molecule at (x, y, z) act as hydrogen-bond donors, respectively, to atoms O4B and O32B in the molecules at (1/2 + x, 1/2 - y, 1 - z) and (1 - x, -1/2 + y, 1/2 - z), so forming, respectively, a C(5) chain parallel to [100] generated by the screw axis along (x, 1/4, 1/2), and a C(7) chain parallel to [010] generated by the screw axis along (1/2, y, 1/4). The combination of the two hydrogen bonds generates a C22(16) chain running parallel to the [001] direction (Fig. 3), and the combination of the [100], [010] and [001] chains generates a three-dimensional framework built solely from type B molecules, all of R configuration.

The two frameworks, of type A and type B molecules, respectively, are necessarily continuously interwoven, and they are linked by the single hydrogen bond between the two molecular types. Within the selected asymmetric unit atom C33B acts as a hydrogen-bond donor to atom O4A and propagation of this interaction links the two interpenetrating networks into a single continuous structure. The type A framework, which contains only molecules of S configuration, has component chains of C(5), C(6) and C22(17) types, while the type B framework, which contains only molecules of R configuration, has component chains of C(5), C(7) and C22(16) types. Hence although each framework is enantiomerically pure, in that it contains just one stereoisomer, the two frameworks thus formed are not, in fact, enantiomers of one another.

The structure of rac-2-isopropyl-3-(4-nitrobenzyl)-1,3-thiazolidin-4-one, (II), isomeric with (I), has recently been reported (Cunico et al., 2007) as a proof of the constitution of this class of product, but no discussion of the supramolecular aggregation was given. In fact, the molecules of (II), which crystallizes in space group P21/c with Z' = 1, are linked by pairs of nearly linear C—H···O hydrogen bonds into a cyclic centrosymmetric dimer characterized by an R22(14) motif (Fig. 4). The supramolecular aggregation of compound (II) is thus very much simpler than that of compound (I).

Related literature top

For related literature, see: Allen (2002); Bernstein et al. (1995); Cunico et al. (2007); Dalhus & Görbitz (2000); Flack (1983, 2003); Singh et al. (1981).

Experimental top

A sample of compound (I) was prepared as recently described (Cunico et al., 2007); crystals of (I) suitable for single-crystal X-ray diffraction were obtained by slow evaporation of a solution in a mixture of methanol and heptane (1:1 v/v).

Refinement top

The space group P212121 was uniquely assigned from the systematic absences. All H atoms were located in difference maps, and then treated as riding atoms with C—H distances of 0.95 Å (aromatic), 0.98 Å (CH3), 0.99 Å (CH2) or 1.00 Å (aliphatic CH), and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups and 1.2 for all other H atoms. The correct absolute structure, which establishes that the type A and B molecules have S and R configurations, respectively, was determined by means of the Flack (1983) parameter. A search for possible additional symmetry revealed none.

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The two independent molecules in (I), showing the atom-labelling scheme: (a) a type A molecule of S configuration and (b) a type B molecule of R configuration.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of a C22(17) chain of type A molecules along [010], built from the alternating action of two C—H···O hydrogen bonds. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&) are at the symmetry positions (1/2 + x, 1/2 - y, -z), (2 - x, 1/2 + y, 1/2 - z), (3/2 - x, 1 - y, 1/2 + z), and (x, 1 + y, z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of a C22(16) chain of type B molecules along [001], built from the alternating action of two C—H···O hydrogen bonds. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&) are at the symmetry positions (1/2 + x, 1/2 - y, 1 - z), (3/2 - x, 1 - y, 1/2 + z), (1 - x, 1/2 + y, 3/2 - z) and (x, y, 1 + z), respectively.
[Figure 4] Fig. 4. Part of the crystal structure of (II), showing the formation of a centrosymmetric R22(14) dimer. The atom coordinates and the atom labelling are those in the original publication (Cunico et al., 2007), and for the sake of clarity, H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (2 - x, -y, -z).
rac-2-isopropyl-3-(2-nitrobenzyl)-1,3-thiazolidin-4-one top
Crystal data top
C13H16N2O3SF(000) = 1184
Mr = 280.34Dx = 1.392 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6032 reflections
a = 11.7604 (4) Åθ = 1.9–27.5°
b = 14.9847 (7) ŵ = 0.25 mm1
c = 15.1844 (8) ÅT = 120 K
V = 2675.9 (2) Å3Plate, colourless
Z = 80.28 × 0.14 × 0.03 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
6032 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode4005 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 1.9°
ϕ & ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1919
Tmin = 0.944, Tmax = 0.993l = 1619
21265 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0285P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
6032 reflectionsΔρmax = 0.26 e Å3
347 parametersΔρmin = 0.27 e Å3
0 restraintsAbsolute structure: Flack (1983), 2596 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (6)
Crystal data top
C13H16N2O3SV = 2675.9 (2) Å3
Mr = 280.34Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 11.7604 (4) ŵ = 0.25 mm1
b = 14.9847 (7) ÅT = 120 K
c = 15.1844 (8) Å0.28 × 0.14 × 0.03 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
6032 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
4005 reflections with I > 2σ(I)
Tmin = 0.944, Tmax = 0.993Rint = 0.074
21265 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.083Δρmax = 0.26 e Å3
S = 0.99Δρmin = 0.27 e Å3
6032 reflectionsAbsolute structure: Flack (1983), 2596 Friedel pairs
347 parametersAbsolute structure parameter: 0.02 (6)
0 restraints
Special details top

Experimental. The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.73562 (5)0.44125 (5)0.09125 (5)0.03220 (19)
C2A0.80579 (19)0.35848 (15)0.01969 (18)0.0225 (6)
C21A0.87413 (19)0.40015 (16)0.05529 (19)0.0242 (6)
C22A0.9717 (2)0.45510 (18)0.0178 (2)0.0327 (7)
C23A0.8010 (2)0.45535 (17)0.11769 (19)0.0306 (7)
N3A0.71355 (15)0.30044 (12)0.00968 (15)0.0221 (5)
C37A0.7381 (2)0.21616 (15)0.05331 (18)0.0235 (6)
C31A0.75648 (18)0.13942 (15)0.01051 (17)0.0188 (6)
C32A0.78679 (19)0.05272 (17)0.01411 (18)0.0226 (6)
N32A0.79677 (18)0.02855 (15)0.10840 (17)0.0305 (6)
O31A0.75775 (18)0.07915 (13)0.16375 (13)0.0418 (5)
O32A0.84301 (17)0.04289 (14)0.12649 (15)0.0498 (6)
C33A0.8058 (2)0.01527 (16)0.0452 (2)0.0271 (7)
C34A0.7920 (2)0.00135 (17)0.1339 (2)0.0292 (7)
C35A0.7603 (2)0.08504 (17)0.16129 (19)0.0283 (6)
C36A0.74425 (19)0.15284 (16)0.10026 (18)0.0238 (6)
C4A0.6039 (2)0.32574 (16)0.0040 (2)0.0269 (7)
O4A0.52147 (14)0.28187 (11)0.01830 (14)0.0353 (5)
C5A0.59608 (19)0.41524 (16)0.0485 (2)0.0302 (7)
S1B0.42204 (6)0.14265 (5)0.68231 (5)0.03122 (19)
C2B0.48074 (19)0.22471 (16)0.60587 (19)0.0236 (6)
C21B0.54193 (19)0.30361 (17)0.65024 (18)0.0236 (6)
C22B0.6447 (2)0.26913 (19)0.7012 (2)0.0361 (8)
C23B0.4641 (2)0.35826 (18)0.7091 (2)0.0355 (7)
N3B0.38369 (15)0.25240 (13)0.55199 (15)0.0225 (5)
C37B0.4022 (2)0.30116 (16)0.47045 (18)0.0259 (6)
C31B0.42663 (18)0.24179 (15)0.39236 (17)0.0189 (6)
C32B0.46195 (19)0.27236 (15)0.30996 (19)0.0216 (6)
N32B0.48013 (18)0.36842 (15)0.29427 (17)0.0292 (6)
O31B0.43117 (17)0.42270 (12)0.34197 (14)0.0393 (5)
O32B0.54409 (16)0.38963 (13)0.23396 (15)0.0459 (6)
C33B0.4835 (2)0.21712 (18)0.2387 (2)0.0292 (7)
C34B0.4718 (2)0.12603 (18)0.2497 (2)0.0317 (7)
C35B0.4387 (2)0.09256 (17)0.32991 (19)0.0273 (6)
C36B0.41661 (19)0.14913 (15)0.39991 (18)0.0228 (6)
C4B0.2773 (2)0.23295 (16)0.58051 (19)0.0272 (6)
O4B0.19034 (14)0.25286 (13)0.54084 (14)0.0373 (5)
C5B0.2788 (2)0.18309 (18)0.6664 (2)0.0315 (7)
H2A0.85890.32230.05670.027*
H21A0.90820.35030.09030.029*
H22D0.94100.50480.01680.049*
H22E1.01890.41730.02020.049*
H22F1.01810.47860.06610.049*
H23D0.77120.50760.08640.046*
H23E0.84710.47500.16780.046*
H23F0.73750.41890.13900.046*
H31A0.67420.20110.09310.028*
H32A0.80720.22330.08990.028*
H33A0.82810.07280.02520.032*
H34A0.80440.04480.17570.035*
H35A0.74940.09660.22220.034*
H36A0.72410.21060.12080.029*
H51A0.57190.46140.00570.036*
H52A0.53990.41310.09690.036*
H2B0.53650.19360.56680.028*
H21B0.57060.34380.60260.028*
H22A0.68820.31980.72430.054*
H22B0.69310.23380.66190.054*
H22C0.61890.23170.75020.054*
H23A0.43810.32130.75840.053*
H23B0.39840.37880.67510.053*
H23C0.50580.41000.73200.053*
H31B0.46690.34260.47870.031*
H32B0.33390.33750.45760.031*
H33B0.50570.24130.18350.035*
H34B0.48660.08670.20190.038*
H35B0.43090.02990.33740.033*
H36B0.39400.12420.45470.027*
H51B0.25680.22320.71540.038*
H52B0.22470.13250.66450.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0284 (3)0.0339 (4)0.0343 (5)0.0007 (3)0.0035 (3)0.0101 (3)
C2A0.0197 (11)0.0212 (13)0.0268 (18)0.0018 (11)0.0003 (11)0.0020 (13)
C21A0.0205 (12)0.0218 (13)0.0305 (19)0.0017 (11)0.0015 (12)0.0035 (13)
C22A0.0238 (13)0.0302 (14)0.044 (2)0.0035 (12)0.0011 (13)0.0015 (15)
C23A0.0310 (14)0.0312 (15)0.0297 (19)0.0007 (13)0.0001 (13)0.0025 (14)
N3A0.0194 (10)0.0195 (10)0.0274 (15)0.0013 (9)0.0002 (10)0.0006 (10)
C37A0.0249 (12)0.0238 (13)0.0219 (16)0.0036 (11)0.0005 (12)0.0032 (12)
C31A0.0164 (11)0.0226 (12)0.0174 (16)0.0027 (11)0.0027 (11)0.0015 (12)
C32A0.0205 (12)0.0261 (13)0.0211 (17)0.0042 (11)0.0003 (11)0.0054 (13)
N32A0.0245 (11)0.0322 (13)0.0346 (18)0.0070 (11)0.0017 (11)0.0088 (13)
O31A0.0676 (13)0.0344 (11)0.0235 (13)0.0055 (10)0.0020 (11)0.0020 (10)
O32A0.0504 (13)0.0490 (13)0.0501 (16)0.0194 (11)0.0017 (11)0.0231 (12)
C33A0.0215 (13)0.0214 (13)0.038 (2)0.0018 (11)0.0004 (13)0.0029 (14)
C34A0.0236 (14)0.0316 (15)0.032 (2)0.0003 (13)0.0054 (13)0.0067 (14)
C35A0.0281 (13)0.0345 (15)0.0223 (17)0.0006 (12)0.0029 (12)0.0012 (13)
C36A0.0233 (13)0.0229 (13)0.0253 (18)0.0013 (11)0.0013 (12)0.0020 (12)
C4A0.0228 (13)0.0270 (14)0.0309 (19)0.0012 (12)0.0018 (13)0.0084 (13)
O4A0.0230 (9)0.0366 (11)0.0462 (15)0.0077 (8)0.0013 (9)0.0004 (10)
C5A0.0228 (13)0.0308 (15)0.037 (2)0.0014 (12)0.0021 (13)0.0004 (14)
S1B0.0276 (3)0.0333 (4)0.0328 (5)0.0021 (3)0.0017 (3)0.0095 (4)
C2B0.0171 (11)0.0316 (15)0.0222 (17)0.0011 (11)0.0037 (11)0.0056 (13)
C21B0.0217 (12)0.0278 (14)0.0211 (17)0.0025 (12)0.0013 (11)0.0024 (12)
C22B0.0268 (14)0.0489 (18)0.033 (2)0.0031 (13)0.0088 (13)0.0032 (16)
C23B0.0403 (16)0.0353 (16)0.031 (2)0.0030 (14)0.0015 (14)0.0095 (15)
N3B0.0199 (10)0.0277 (11)0.0198 (15)0.0005 (9)0.0011 (9)0.0009 (11)
C37B0.0302 (14)0.0218 (13)0.0256 (18)0.0008 (12)0.0057 (12)0.0016 (13)
C31B0.0159 (11)0.0181 (12)0.0228 (17)0.0003 (10)0.0021 (11)0.0009 (12)
C32B0.0192 (12)0.0191 (13)0.0265 (18)0.0027 (10)0.0025 (12)0.0031 (13)
N32B0.0252 (12)0.0285 (13)0.0340 (17)0.0027 (11)0.0100 (11)0.0118 (13)
O31B0.0611 (13)0.0225 (10)0.0341 (14)0.0009 (10)0.0068 (11)0.0009 (10)
O32B0.0337 (11)0.0452 (13)0.0589 (17)0.0051 (10)0.0106 (11)0.0257 (12)
C33B0.0237 (13)0.0382 (18)0.0257 (19)0.0035 (13)0.0041 (12)0.0027 (15)
C34B0.0308 (14)0.0366 (17)0.0277 (19)0.0045 (13)0.0030 (14)0.0086 (15)
C35B0.0292 (14)0.0203 (13)0.0324 (19)0.0013 (12)0.0024 (13)0.0046 (13)
C36B0.0230 (12)0.0226 (13)0.0229 (17)0.0020 (11)0.0003 (12)0.0029 (13)
C4B0.0253 (13)0.0262 (14)0.0301 (19)0.0001 (12)0.0027 (13)0.0062 (13)
O4B0.0218 (9)0.0462 (11)0.0438 (15)0.0052 (9)0.0084 (9)0.0023 (11)
C5B0.0248 (13)0.0384 (15)0.0313 (19)0.0031 (12)0.0077 (13)0.0011 (14)
Geometric parameters (Å, º) top
S1A—C5A1.808 (2)S1B—C5B1.806 (3)
S1A—C2A1.844 (2)S1B—C2B1.826 (3)
C2A—N3A1.460 (3)C2B—N3B1.464 (3)
C2A—C21A1.527 (3)C2B—C21B1.539 (3)
C2A—H2A1.00C2B—H2B1.00
C21A—C22A1.523 (3)C21B—C23B1.519 (4)
C21A—C23A1.524 (4)C21B—C22B1.525 (3)
C21A—H21A1.00C21B—H21B1.00
C22A—H22D0.98C22B—H22A0.98
C22A—H22E0.98C22B—H22B0.98
C22A—H22F0.98C22B—H22C0.98
C23A—H23D0.98C23B—H23A0.98
C23A—H23E0.98C23B—H23B0.98
C23A—H23F0.98C23B—H23C0.98
N3A—C4A1.360 (3)N3B—C4B1.356 (3)
N3A—C37A1.455 (3)N3B—C37B1.454 (3)
C37A—C31A1.519 (3)C37B—C31B1.510 (3)
C37A—H31A0.99C37B—H31B0.99
C37A—H32A0.99C37B—H32B0.99
C31A—C36A1.385 (4)C31B—C32B1.396 (4)
C31A—C32A1.398 (3)C31B—C36B1.398 (3)
C32A—C33A1.378 (4)C32B—C33B1.386 (4)
C32A—N32A1.482 (3)C32B—N32B1.475 (3)
N32A—O31A1.221 (3)N32B—O32B1.227 (3)
N32A—O32A1.232 (3)N32B—O31B1.232 (3)
C33A—C34A1.379 (4)C33B—C34B1.382 (4)
C33A—H33A0.95C33B—H33B0.95
C34A—C35A1.373 (4)C34B—C35B1.374 (4)
C34A—H34A0.95C34B—H34B0.95
C35A—C36A1.388 (3)C35B—C36B1.384 (4)
C35A—H35A0.95C35B—H35B0.95
C36A—H36A0.95C36B—H36B0.95
C4A—O4A1.219 (3)C4B—O4B1.224 (3)
C4A—C5A1.504 (4)C4B—C5B1.503 (4)
C5A—H51A0.99C5B—H51B0.99
C5A—H52A0.99C5B—H52B0.99
C5A—S1A—C2A92.83 (11)C5B—S1B—C2B92.38 (12)
N3A—C2A—C21A114.0 (2)N3B—C2B—C21B113.0 (2)
N3A—C2A—S1A104.37 (15)N3B—C2B—S1B104.55 (15)
C21A—C2A—S1A113.57 (16)C21B—C2B—S1B114.6 (2)
N3A—C2A—H2A108.2N3B—C2B—H2B108.1
C21A—C2A—H2A108.2C21B—C2B—H2B108.1
S1A—C2A—H2A108.2S1B—C2B—H2B108.1
C22A—C21A—C23A111.4 (2)C23B—C21B—C22B111.2 (2)
C22A—C21A—C2A109.8 (2)C23B—C21B—C2B112.97 (19)
C23A—C21A—C2A112.8 (2)C22B—C21B—C2B109.4 (2)
C22A—C21A—H21A107.5C23B—C21B—H21B107.7
C23A—C21A—H21A107.5C22B—C21B—H21B107.7
C2A—C21A—H21A107.5C2B—C21B—H21B107.7
C21A—C22A—H22D109.5C21B—C22B—H22A109.5
C21A—C22A—H22E109.5C21B—C22B—H22B109.5
H22D—C22A—H22E109.5H22A—C22B—H22B109.5
C21A—C22A—H22F109.5C21B—C22B—H22C109.5
H22D—C22A—H22F109.5H22A—C22B—H22C109.5
H22E—C22A—H22F109.5H22B—C22B—H22C109.5
C21A—C23A—H23D109.5C21B—C23B—H23A109.5
C21A—C23A—H23E109.5C21B—C23B—H23B109.5
H23D—C23A—H23E109.5H23A—C23B—H23B109.5
C21A—C23A—H23F109.5C21B—C23B—H23C109.5
H23D—C23A—H23F109.5H23A—C23B—H23C109.5
H23E—C23A—H23F109.5H23B—C23B—H23C109.5
C4A—N3A—C37A120.0 (2)C4B—N3B—C37B121.2 (2)
C4A—N3A—C2A119.5 (2)C4B—N3B—C2B118.7 (2)
C37A—N3A—C2A120.56 (18)C37B—N3B—C2B120.09 (19)
N3A—C37A—C31A113.2 (2)N3B—C37B—C31B113.6 (2)
N3A—C37A—H31A108.9N3B—C37B—H31B108.8
C31A—C37A—H31A108.9C31B—C37B—H32B108.8
N3A—C37A—H32A108.9N3B—C37B—H31B108.8
C31A—C37A—H32A108.9C31B—C37B—H32B108.8
H31A—C37A—H32A107.7H31B—C37B—H32B107.7
C36A—C31A—C32A115.1 (2)C32B—C31B—C36B115.1 (2)
C36A—C31A—C37A120.2 (2)C32B—C31B—C37B124.6 (2)
C32A—C31A—C37A124.7 (2)C36B—C31B—C37B120.3 (2)
C33A—C32A—C31A123.6 (3)C33B—C32B—C31B123.9 (2)
C33A—C32A—N32A116.0 (2)C33B—C32B—N32B115.5 (2)
C31A—C32A—N32A120.4 (2)C31B—C32B—N32B120.6 (2)
O31A—N32A—O32A123.5 (3)O32B—N32B—O31B123.7 (2)
O31A—N32A—C32A118.9 (2)O32B—N32B—C32B117.5 (2)
O32A—N32A—C32A117.6 (2)O31B—N32B—C32B118.8 (2)
C32A—C33A—C34A119.0 (2)C34B—C33B—C32B118.5 (3)
C32A—C33A—H33A120.5C34B—C33B—H33B120.7
C34A—C33A—H33A120.5C32B—C33B—H33B120.7
C35A—C34A—C33A119.5 (3)C35B—C34B—C33B119.7 (3)
C35A—C34A—H34A120.2C35B—C34B—H34B120.1
C33A—C34A—H34A120.2C33B—C34B—H34B120.1
C34A—C35A—C36A120.2 (3)C34B—C35B—C36B120.7 (2)
C34A—C35A—H35A119.9C34B—C35B—H35B119.6
C36A—C35A—H35A119.9C36B—C35B—H35B119.6
C31A—C36A—C35A122.4 (2)C35B—C36B—C31B122.0 (2)
C31A—C36A—H36A118.8C35B—C36B—H36B119.0
C35A—C36A—H36A118.8C31B—C36B—H36B119.0
O4A—C4A—N3A124.1 (2)O4B—C4B—N3B124.2 (3)
O4A—C4A—C5A123.8 (2)O4B—C4B—C5B123.9 (2)
N3A—C4A—C5A112.0 (2)N3B—C4B—C5B111.9 (2)
C4A—C5A—S1A107.34 (17)C4B—C5B—S1B107.11 (18)
C4A—C5A—H51A110.2C4B—C5B—H52B110.3
S1A—C5A—H51A110.2S1B—C5B—H52B110.3
C4A—C5A—H52A110.2C4B—C5B—H51B110.3
S1A—C5A—H52A110.2S1B—C5B—H51B110.3
H51A—C5A—H52A108.5H51B—C5B—H52B108.5
C5A—S1A—C2A—N3A17.05 (19)C5B—S1B—C2B—N3B20.29 (18)
C5A—S1A—C2A—C21A107.70 (19)C5B—S1B—C2B—C21B103.98 (19)
N3A—C2A—C21A—C22A176.94 (19)S1B—C2B—C21B—C23B61.4 (3)
S1A—C2A—C21A—C22A63.7 (2)N3B—C2B—C21B—C22B177.3 (2)
N3A—C2A—C21A—C23A58.2 (3)N3B—C2B—C21B—C23B58.3 (3)
S1A—C2A—C21A—C23A61.2 (2)S1B—C2B—C21B—C22B63.0 (2)
C21A—C2A—N3A—C4A112.1 (3)C21B—C2B—N3B—C4B109.5 (2)
S1A—C2A—N3A—C4A12.4 (3)S1B—C2B—N3B—C4B15.8 (3)
C21A—C2A—N3A—C37A67.9 (3)C21B—C2B—N3B—C37B69.4 (3)
S1A—C2A—N3A—C37A167.64 (18)S1B—C2B—N3B—C37B165.31 (18)
C4A—N3A—C37A—C31A93.7 (3)C4B—N3B—C37B—C31B96.7 (3)
C2A—N3A—C37A—C31A86.4 (3)C2B—N3B—C37B—C31B84.4 (3)
N3A—C37A—C31A—C36A2.8 (3)N3B—C37B—C31B—C32B171.1 (2)
N3A—C37A—C31A—C32A176.7 (2)N3B—C37B—C31B—C36B7.6 (3)
C36A—C31A—C32A—C33A1.2 (3)C36B—C31B—C32B—C33B1.6 (4)
C37A—C31A—C32A—C33A178.3 (2)C37B—C31B—C32B—C33B179.6 (2)
C36A—C31A—C32A—N32A176.9 (2)C36B—C31B—C32B—N32B177.6 (2)
C37A—C31A—C32A—N32A3.6 (3)C37B—C31B—C32B—N32B1.1 (4)
C33A—C32A—N32A—O31A164.4 (2)C33B—C32B—N32B—O32B22.6 (3)
C31A—C32A—N32A—O31A13.9 (3)C31B—C32B—N32B—O32B156.8 (2)
C33A—C32A—N32A—O32A14.6 (3)C33B—C32B—N32B—O31B157.6 (2)
C31A—C32A—N32A—O32A167.2 (2)C31B—C32B—N32B—O31B23.1 (3)
C31A—C32A—C33A—C34A1.6 (4)C31B—C32B—C33B—C34B1.4 (4)
N32A—C32A—C33A—C34A176.6 (2)N32B—C32B—C33B—C34B177.9 (2)
C32A—C33A—C34A—C35A0.3 (4)C32B—C33B—C34B—C35B0.5 (4)
C33A—C34A—C35A—C36A1.1 (4)C33B—C34B—C35B—C36B0.1 (4)
C32A—C31A—C36A—C35A0.3 (3)C34B—C35B—C36B—C31B0.1 (4)
C37A—C31A—C36A—C35A179.8 (2)C32B—C31B—C36B—C35B0.9 (4)
C34A—C35A—C36A—C31A1.5 (4)C37B—C31B—C36B—C35B179.8 (2)
C37A—N3A—C4A—O4A0.1 (4)C37B—N3B—C4B—O4B1.1 (4)
C2A—N3A—C4A—O4A179.9 (3)C2B—N3B—C4B—O4B180.0 (3)
C37A—N3A—C4A—C5A179.0 (2)C37B—N3B—C4B—C5B179.5 (2)
C2A—N3A—C4A—C5A0.9 (4)C2B—N3B—C4B—C5B0.6 (3)
O4A—C4A—C5A—S1A166.8 (3)O4B—C4B—C5B—S1B164.1 (2)
N3A—C4A—C5A—S1A14.3 (3)N3B—C4B—C5B—S1B15.3 (3)
C2A—S1A—C5A—C4A18.1 (2)C2B—S1B—C5B—C4B20.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2A—H2A···O4Ai1.002.543.295 (3)132
C2B—H2B···O4Bii1.002.563.337 (4)134
C34A—H34A···O31Aiii0.952.603.355 (4)137
C35B—H35B···O32Biv0.952.383.196 (4)144
C33B—H33B···O4A0.952.593.512 (4)165
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y+1/2, z+1; (iii) x+3/2, y, z1/2; (iv) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H16N2O3S
Mr280.34
Crystal system, space groupOrthorhombic, P212121
Temperature (K)120
a, b, c (Å)11.7604 (4), 14.9847 (7), 15.1844 (8)
V3)2675.9 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.28 × 0.14 × 0.03
Data collection
DiffractometerBruker–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.944, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
21265, 6032, 4005
Rint0.074
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.083, 0.99
No. of reflections6032
No. of parameters347
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.27
Absolute structureFlack (1983), 2596 Friedel pairs
Absolute structure parameter0.02 (6)

Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected torsion angles (º) top
N3A—C2A—C21A—C22A176.94 (19)N3B—C2B—C21B—C22B177.3 (2)
N3A—C2A—C21A—C23A58.2 (3)N3B—C2B—C21B—C23B58.3 (3)
C2A—N3A—C37A—C31A86.4 (3)C2B—N3B—C37B—C31B84.4 (3)
N3A—C37A—C31A—C32A176.7 (2)N3B—C37B—C31B—C32B171.1 (2)
C31A—C32A—N32A—O31A13.9 (3)C31B—C32B—N32B—O31B23.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2A—H2A···O4Ai1.002.543.295 (3)132
C2B—H2B···O4Bii1.002.563.337 (4)134
C34A—H34A···O31Aiii0.952.603.355 (4)137
C35B—H35B···O32Biv0.952.383.196 (4)144
C33B—H33B···O4A0.952.593.512 (4)165
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y+1/2, z+1; (iii) x+3/2, y, z1/2; (iv) x+1, y1/2, z+1/2.
 

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