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In the title compound, C21H18N2OS2, a strong intra­molecular N—H...O hydrogen bond [N...O = 2.642 (3) Å] between the amide N atom and the benzoyl O atom forms an almost planar six-membered ring in the central part of the mol­ecule. In the crystal, mol­ecules are packed through weak N—H...S inter­actions. Intra- and inter­molecular hydrogen bonds and van der Waals inter­actions are the stabilizing forces for the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112045167/fn3118sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112045167/fn3118Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112045167/fn3118Isup3.cml
Supplementary material

CCDC reference: 893650

Comment top

Thioureas have been mentioned in the syntheses of heterocycles (Singh et al., 2006) and coordination complexes (Kemp et al., 1997), and mostly in medicinal chemistry (Murtaza et al., 2012). They have been shown to possess antitubercular, antithroid, anthelmintic, antibacterial, insecticidal and rodenticidal properties (Schroeder, 1955; Huebhr et al., 1953; Madan & Taneja, 1991). These have also been found as interesting organic inhibitors for corrosion activity (Koch & Bourne, 1998). In recent years, the structures and intra- and intermolecular hydrogen-bonding behaviour of some N-aryl-N'-benzoylthioureas have been thoroughly investigated (Zhang et al., 1996; Cao et al., 1996; Dago et al., 1989; Kaminsky et al., 2002). Single-crystal X-ray diffraction studies of these thioureas have revealed the existence of a six-membered ring formed by intramolecular hydrogen bonds between the carbonyl O atom and an NH H atom (Weiqun et al., 2003). These features prompted us to study the antibacterial activity, structure and hydrogen-bonding interactions of an N-aryl-N'-benzoylthiourea with benzylsulfanyl as a substituent on the aryl ring. In this paper, the solid-state synthesis, characterization, crystal structure and antibacterial activity of 1-benzoyl-3-[(2-benzylsulfanyl)phenyl]thiourea, (I), are presented.

Compound (I) is synthesized by an environmentally friendly solid-state pasting and grinding method without using any hazardous organic solvent (Fig. 1). The FT–IR spectrum of (I) shows absorption bands at 3328 cm-1 for ν(N—H), at 1336 cm-1 for ν(C—N) and at 748 cm-1 for ν(CS). The absorption band at 748 cm-1 for ν(CS) proves the formation of the thiourea compound (Bombicz et al., 2004). The strong absorption band ν(CO) for (I) is at 1671 cm-1, apparently decreased in frequency as compared with typical carbonyl absorption (1700 cm-1). This is interpreted as being a result of its conjugated resonance with the phenyl ring and the possible formation of an intramolecular hydrogen bond with an N—H group. In the electronic spectrum of (I), absorption bands are observed at λmax = 240 nm and λmax = 270 nm. The broad absorption band observed in the region between λmax = 240 nm to λmax = 320 nm is due to ππ conjugation of the phenyl rings (ππ* transition) and orbital overlapping between CO and CS groups. The 1 NMR spectrum in CDCl3 (400 MHz spectrometer) shows the N—H resonance considerably downfield from other resonances in the spectrum. The chemical shift for N—H was found as a singlet at δ 12.73 for the H atom in the hydrogen bond. Another singlet of N—H was at about at δ 9.07. Two benzyl H atoms appear as singlet at δ 4.02. Aromatic H atoms appear around δ 7.21–8.33. The 13C NMR spectrum in CDCl3 (100 MHz) shows peaks at δ 178.45, 166.28 and 39.99 for CS, CO and benzyl C atom, respectively. Peaks at δ 127.08–133.69 correspond to the aromatic carbons.

Single crystals of (I) suitable for X-ray analysis were grown from methanol–dichloromethane (1:1 v/v). The analysis of (I) shows that it crystallizes in the monoclinic space group P21/c with four molecules in the unit cell. In the molecule, the C7—O1 and C8—S2 bonds show a typical double-bond character (Table 1). All the C—N bonds are indicative of partial double-bond character. The C8—N1 bond, due to its proximity to the carbonyl group, is slightly shorter compared to the C9—N2 bond (Zhang et al., 1996; Jin et al., 1997). These bond lengths are in agreement with the corresponding distances observed in other 1-benzoyl-3-phenylthiourea molecules reported in the Cambridge Structural Database (Allen, 2002) [refcodes refcodes AMEBOJ (Arslan et al., 2003), ERENUK (Weiqun et al., 2004), GUWFIN (Yamin & Yusof, 2003b), HOFHIT (Raj et al., 1999), HURYAU (Yamin & Yusof, 2003a), PUYWIP (Usman et al., 2002), UKOQUG (Weiqun et al. , 2003), WIRSEV (Zhang et al., 1996) and XEQDAY (Li et al., 2000)].

Like other N-benzoyl-N'-phenylthioureas, thiourea (I) possesses intra- and intermolecular hydrogen-bonding interactions, as shown in Table 2. The strong intramolecular hydrogen-bond-like N2—H1N2···O1 interaction (Table 2) between the carbonyl O1 atom and an NH proton, forming a six-membered ring, and a weak intramolecular C14—H14···S2 interaction (Table 2), forming an S(6) ring, stabilize the molecular geometry and crystal packing along with two other intramolecular hydrogen bonds (N2—H1N2···S1 and C6—H6···O1), forming a five-membered ring, and van der Waals interactions.

The Crystal structure of (I) is further stabilized by three intermolecular hydrogen bonds (N1—H1N1···S2i, C2—H2A···S2i and C15—H15A···O1ii; Table 2). Atoms S2, C8, N1 and H1N1 form an eight-membered hydrogen-bonded ring, resulting in a dimer around an inversion centre, as shown in Fig. 2. These five-, six- and eight-membered hydrogen-bonded rings can be described by graph-set motifs S(5), S(6) and R22(8), respectively (Fig. 2).

From the MIC (minimum inhibitory concentration) study of (I) (see Experimental), it can be seen that the compound has some amount of inhibitory activity against Gram positive and Gram negative bacteria. Bacillus subtilis, Klebsiella pneumoniae and Esherichia coli are seen to be inhibited at a concentration of 3.125, 6.25 and 12.50 g l-1 of (I), respectively.

Related literature top

For related literature, see: Allen (2002); Arslan et al. (2003); Bombicz et al. (2004); Cao et al. (1996); Dago et al. (1989); Huebhr et al. (1953); Jin et al. (1997); Kaminsky et al. (2002); Kemp et al. (1997); Koch & Bourne (1998); Li et al. (2000); Madan & Taneja (1991); Murtaza et al. (2012); Raj et al. (1999); Rangasamy et al. (2007); Schroeder (1955); Shi et al. (2006); Singh et al. (2006); Usman et al. (2002); Weiqun et al. (2003, 2004); Yamin & Yusof (2003a, 2003b); Zhang et al. (1996).

Experimental top

2-(Benzylsulfanyl)aniline was synthesized according to the literature procedure of Shi et al. (2006). All the chemicals used were of Merck purity. In a typical procedure, benzoyl chloride (1.16 ml, 0.01 mol) was added dropwise to a solution of ammonium thiocyanate (0.76 g, 0.01 mol) in water (10 ml) and stirred for 1 h. The solid formed was filtered off, dried between sheets of filter paper and mixed with 2-(benzylsulfanyl)aniline (2.15 g, 0.01 mol). The solid mixture was then ground well in an agate mortar for 30 min, extracted with acetone and diluted with cold water. The solid thiourea which formed was filtered off, dried and recrystallized from methanol–dichloromethane (1:1 v/v) to obtain white crystals suitable for X-ray diffraction analysis (yield 90%; m.p. 369 K). 1H NMR (TMS, CDCl3): δ 12.73 (s, 1H), 9.07 (s, 1H), 8.32 (d, J = 8.28 Hz, 1H), 7.93 (d, J = 6.88 Hz, 2H), 7.66 (t, J = 8 Hz, 1H), 7.55 (t, J = 8.1 Hz, 2H), 7.41 (d, J = 8 Hz, 1H), 7.34 (t, J = 8 Hz, 1H), 7.12–7.21 (m, 6H), 4.02 (s, 2H). 13C NMR (TMS, CDCl3): δ 178.45, 166.28, 133.69, 129.22, 128.99, 128.42, 127.62, 127.27, 127.08, 39.99. FT–IR (KBr) νmax (cm-1): (CO) 1671, (N—H) 3328, (C—N) 1336, (CS) 748. UV–Visible (λmax, EtOH): 240, 206. Analysis calculated for C21H18N2S2O: C 66.66, H 4.76, N 7.40%; found: C 66.39, H 4.70, N 7.21%.

In the antibacterial study, the MIC value of the synthesized compound was determined using the literature method of Rangasamy et al. (2007). Klebsiella pneumoniae and Escherichia Coli as Gram negative and Bacillus subtilis as Gram positive strains of bacteria was taken for the study. These bacteria were cultured in Luria broth (LB) media and cultures were grown until they obtained a growth equivalent to 0.5 McFarland's Standard. A stock solution of 25 g l-1 in 100% dimethyl sulfoxide of the compound was prepared. The MIC was determined using 96 well plates. 200 µl of the compound from the stock solution was added to the first well. From the second well to the eighth well, 100 µl of LB media was added. Now from the first well 100 µl of the solution was taken and added to the second well and subsequently serially diluted until the eighth well had a concentration of 195 µg ml-1. To all the wells, 100 µl of both the bacterial inoculum was added. The plates were then incubated at 310 K overnight. After the incubation period, 40 µl of MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] solution [at a concentration of 0.2 g l-1 of Phosphate Buffer Saline (pH 7.4)] was added to each well. The plates were again incubated for 40 min at 310 K. After the incubation period, the plates were observed for any change in color. A change of colour to blue indicated bacterial growth signifying that the compounds do not have any inhibitory activity while no change of colour indicates a positive result indicating inhibitory activity of the compounds.

Refinement top

H atoms were placed in calculated positions, with C—H = 0.95 and 0.99 Å for aromatic and benzyl H atoms, respectively, and refined as riding atoms with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996).

Figures top
[Figure 1] Fig. 1. The molecular struicture of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A capped-sticks diagram showing the formation of the dimer of (I) via hydrogen bonding.
1-Benzoyl-3-[(2-benzylsulfanyl)phenyl]thiourea top
Crystal data top
C21H18N2OS2F(000) = 792
Mr = 378.49Dx = 1.365 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 19.8574 (18) ÅCell parameters from 1378 reflections
b = 4.9195 (5) Åθ = 2.6–24.3°
c = 19.6197 (18) ŵ = 0.30 mm1
β = 106.089 (2)°T = 100 K
V = 1841.5 (3) Å3Needle, colourless
Z = 40.49 × 0.04 × 0.04 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3231 independent reflections
Radiation source: fine-focus sealed tube2488 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 2123
Tmin = 0.866, Tmax = 0.990k = 55
8509 measured reflectionsl = 2317
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0507P)2]
where P = (Fo2 + 2Fc2)/3
3231 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C21H18N2OS2V = 1841.5 (3) Å3
Mr = 378.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 19.8574 (18) ŵ = 0.30 mm1
b = 4.9195 (5) ÅT = 100 K
c = 19.6197 (18) Å0.49 × 0.04 × 0.04 mm
β = 106.089 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3231 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
2488 reflections with I > 2σ(I)
Tmin = 0.866, Tmax = 0.990Rint = 0.063
8509 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.11Δρmax = 0.33 e Å3
3231 reflectionsΔρmin = 0.30 e Å3
235 parameters
Special details top

Experimental. Melting points was determined in an open capillary and was uncorrected. The UV–Visible spectrum was recorded on a Cary100 Bio UV Vis spectrophotometer. The IR spectrum was obtained on a Perkin–Elmer 73633 FT–IR spectrometer as a KBr Pellet. 1H and 13C NMR spectra were recorded on a Varian (400 MHz and 100 MHz) FT NMR spectrometer using TMS as an internal standard and CDCl3 as solvent. The elemental analysis was conducted using CHNS Perkin Elmer Model. 240 analyzer. Single crystal X-ray was collected on Bruker SMART APEX CCD diffractometer.

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 (Å2) top
xyzUiso*/Ueq
S10.35151 (4)0.24021 (17)0.12672 (5)0.0249 (3)
S20.07128 (5)0.3494 (2)0.04484 (5)0.0404 (3)
O10.22284 (11)0.6259 (5)0.16257 (12)0.0280 (6)
N10.12021 (13)0.6122 (6)0.07484 (14)0.0235 (7)
H1N10.07800.68420.06100.028*
N20.19849 (13)0.2955 (5)0.05228 (14)0.0203 (6)
H1N20.22420.35400.09370.024*
C10.13422 (16)0.9309 (6)0.17494 (17)0.0198 (7)
C20.06821 (16)1.0536 (7)0.14910 (19)0.0248 (8)
H2A0.03821.00130.10430.030*
C30.04672 (19)1.2520 (7)0.1891 (2)0.0336 (9)
H30.00191.33350.17160.040*
C40.0898 (2)1.3311 (8)0.2536 (2)0.0342 (9)
H40.07441.46580.28060.041*
C50.1556 (2)1.2153 (8)0.27958 (19)0.0367 (10)
H50.18571.27290.32380.044*
C60.17737 (19)1.0158 (7)0.24078 (18)0.0311 (9)
H60.22220.93510.25900.037*
C70.16287 (16)0.7121 (7)0.13786 (17)0.0201 (8)
C80.13451 (16)0.4126 (7)0.02985 (17)0.0228 (8)
C90.23139 (16)0.0943 (6)0.02050 (17)0.0196 (7)
C100.30378 (17)0.0495 (7)0.05132 (17)0.0227 (8)
C110.33841 (19)0.1509 (7)0.02339 (19)0.0300 (9)
H110.38710.17950.04410.036*
C120.3032 (2)0.3085 (7)0.03384 (19)0.0328 (9)
H120.32730.44490.05210.039*
C130.2322 (2)0.2645 (7)0.06423 (18)0.0330 (9)
H130.20770.37160.10360.040*
C140.19625 (18)0.0648 (7)0.03773 (17)0.0276 (8)
H140.14770.03680.05930.033*
C150.37545 (17)0.0348 (7)0.19253 (18)0.0270 (8)
H15A0.33470.15680.18760.032*
H15B0.41410.14320.18350.032*
C160.39813 (16)0.0774 (7)0.26693 (18)0.0237 (8)
C170.45717 (16)0.0285 (7)0.31547 (18)0.0275 (8)
H170.48460.16240.30060.033*
C180.47652 (18)0.0596 (8)0.3856 (2)0.0336 (9)
H180.51640.01700.41850.040*
C190.4375 (2)0.2601 (8)0.4075 (2)0.0377 (10)
H190.45090.32280.45520.045*
C200.3791 (2)0.3667 (8)0.3589 (2)0.0381 (10)
H200.35230.50290.37370.046*
C210.35907 (19)0.2792 (7)0.2896 (2)0.0318 (9)
H210.31880.35510.25710.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0245 (5)0.0128 (5)0.0372 (5)0.0009 (4)0.0085 (4)0.0012 (4)
S20.0206 (5)0.0634 (8)0.0351 (6)0.0005 (5)0.0043 (4)0.0209 (5)
O10.0242 (13)0.0256 (15)0.0312 (14)0.0052 (11)0.0028 (11)0.0045 (11)
N10.0163 (14)0.0276 (18)0.0271 (16)0.0025 (12)0.0069 (12)0.0029 (13)
N20.0226 (15)0.0174 (17)0.0212 (15)0.0015 (12)0.0062 (12)0.0032 (12)
C10.0251 (17)0.0101 (18)0.0275 (19)0.0026 (14)0.0126 (14)0.0056 (14)
C20.0223 (17)0.016 (2)0.038 (2)0.0054 (14)0.0114 (15)0.0007 (15)
C30.033 (2)0.018 (2)0.055 (3)0.0060 (17)0.0208 (19)0.0081 (18)
C40.052 (2)0.020 (2)0.040 (2)0.0081 (18)0.028 (2)0.0046 (17)
C50.060 (3)0.027 (2)0.024 (2)0.0125 (19)0.0123 (19)0.0005 (17)
C60.038 (2)0.029 (2)0.026 (2)0.0105 (17)0.0088 (16)0.0084 (17)
C70.0242 (18)0.0152 (19)0.0223 (18)0.0047 (14)0.0086 (14)0.0061 (14)
C80.0259 (18)0.022 (2)0.0239 (19)0.0064 (15)0.0129 (15)0.0021 (15)
C90.0313 (18)0.0101 (18)0.0214 (18)0.0048 (14)0.0140 (15)0.0034 (13)
C100.0363 (19)0.0081 (18)0.028 (2)0.0028 (15)0.0153 (16)0.0029 (14)
C110.040 (2)0.016 (2)0.041 (2)0.0043 (16)0.0224 (18)0.0067 (17)
C120.056 (3)0.015 (2)0.035 (2)0.0048 (17)0.026 (2)0.0003 (16)
C130.066 (3)0.015 (2)0.023 (2)0.0058 (19)0.0187 (18)0.0014 (15)
C140.037 (2)0.022 (2)0.025 (2)0.0024 (16)0.0100 (16)0.0001 (15)
C150.0288 (18)0.0107 (19)0.039 (2)0.0006 (15)0.0045 (16)0.0009 (15)
C160.0248 (18)0.0116 (19)0.036 (2)0.0054 (14)0.0105 (15)0.0009 (15)
C170.0221 (18)0.024 (2)0.039 (2)0.0008 (15)0.0117 (16)0.0021 (17)
C180.0279 (19)0.031 (2)0.040 (2)0.0063 (17)0.0077 (17)0.0024 (18)
C190.048 (2)0.031 (2)0.038 (2)0.0111 (19)0.019 (2)0.0035 (18)
C200.051 (2)0.030 (2)0.040 (2)0.0068 (19)0.024 (2)0.0007 (19)
C210.034 (2)0.022 (2)0.042 (2)0.0041 (16)0.0134 (17)0.0038 (17)
Geometric parameters (Å, º) top
S1—C101.786 (3)C9—C101.414 (4)
S1—C151.839 (3)C10—C111.398 (5)
S2—C81.674 (3)C11—C121.384 (5)
O1—C71.230 (4)C11—H110.9500
N1—C71.381 (4)C12—C131.388 (5)
N1—C81.401 (4)C12—H120.9500
N1—H1N10.8800C13—C141.396 (5)
N2—C81.353 (4)C13—H130.9500
N2—C91.421 (4)C14—H140.9500
N2—H1N20.8800C15—C161.508 (5)
C1—C61.401 (4)C15—H15A0.9900
C1—C21.404 (4)C15—H15B0.9900
C1—C71.497 (4)C16—C171.391 (4)
C2—C31.392 (5)C16—C211.406 (5)
C2—H2A0.9500C17—C181.391 (5)
C3—C41.373 (5)C17—H170.9500
C3—H30.9500C18—C191.394 (5)
C4—C51.388 (5)C18—H180.9500
C4—H40.9500C19—C201.385 (5)
C5—C61.382 (5)C19—H190.9500
C5—H50.9500C20—C211.376 (5)
C6—H60.9500C20—H200.9500
C9—C141.401 (4)C21—H210.9500
C10—S1—C1599.77 (15)C12—C11—C10121.4 (3)
C7—N1—C8129.2 (3)C12—C11—H11119.3
C7—N1—H1N1115.4C10—C11—H11119.3
C8—N1—H1N1115.4C11—C12—C13119.1 (3)
C8—N2—C9131.2 (3)C11—C12—H12120.5
C8—N2—H1N2114.4C13—C12—H12120.5
C9—N2—H1N2114.4C12—C13—C14120.9 (3)
C6—C1—C2118.4 (3)C12—C13—H13119.6
C6—C1—C7116.4 (3)C14—C13—H13119.6
C2—C1—C7125.2 (3)C13—C14—C9120.4 (3)
C3—C2—C1120.0 (3)C13—C14—H14119.8
C3—C2—H2A120.0C9—C14—H14119.8
C1—C2—H2A120.0C16—C15—S1111.1 (2)
C4—C3—C2120.6 (3)C16—C15—H15A109.4
C4—C3—H3119.7S1—C15—H15A109.4
C2—C3—H3119.7C16—C15—H15B109.4
C3—C4—C5120.3 (4)S1—C15—H15B109.4
C3—C4—H4119.8H15A—C15—H15B108.0
C5—C4—H4119.8C17—C16—C21118.8 (3)
C6—C5—C4119.7 (4)C17—C16—C15119.7 (3)
C6—C5—H5120.1C21—C16—C15121.5 (3)
C4—C5—H5120.1C18—C17—C16120.7 (3)
C5—C6—C1121.0 (3)C18—C17—H17119.7
C5—C6—H6119.5C16—C17—H17119.7
C1—C6—H6119.5C17—C18—C19120.1 (3)
O1—C7—N1121.1 (3)C17—C18—H18120.0
O1—C7—C1120.9 (3)C19—C18—H18120.0
N1—C7—C1118.0 (3)C20—C19—C18119.1 (4)
N2—C8—N1115.4 (3)C20—C19—H19120.5
N2—C8—S2127.9 (3)C18—C19—H19120.5
N1—C8—S2116.6 (2)C21—C20—C19121.3 (4)
C14—C9—C10118.6 (3)C21—C20—H20119.4
C14—C9—N2124.1 (3)C19—C20—H20119.4
C10—C9—N2117.2 (3)C20—C21—C16120.0 (3)
C11—C10—C9119.6 (3)C20—C21—H21120.0
C11—C10—S1119.3 (3)C16—C21—H21120.0
C9—C10—S1121.0 (3)
C6—C1—C2—C30.8 (5)C14—C9—C10—S1178.7 (2)
C7—C1—C2—C3178.8 (3)N2—C9—C10—S10.3 (4)
C1—C2—C3—C40.5 (5)C15—S1—C10—C1163.3 (3)
C2—C3—C4—C50.5 (5)C15—S1—C10—C9115.4 (3)
C3—C4—C5—C61.2 (6)C9—C10—C11—C120.4 (5)
C4—C5—C6—C10.9 (6)S1—C10—C11—C12178.3 (3)
C2—C1—C6—C50.1 (5)C10—C11—C12—C130.5 (5)
C7—C1—C6—C5179.5 (3)C11—C12—C13—C140.1 (5)
C8—N1—C7—O10.2 (5)C12—C13—C14—C90.3 (5)
C8—N1—C7—C1179.1 (3)C10—C9—C14—C130.4 (5)
C6—C1—C7—O14.3 (5)N2—C9—C14—C13177.9 (3)
C2—C1—C7—O1176.1 (3)C10—S1—C15—C16163.3 (2)
C6—C1—C7—N1176.3 (3)S1—C15—C16—C17136.0 (3)
C2—C1—C7—N13.3 (5)S1—C15—C16—C2147.0 (4)
C9—N2—C8—N1178.3 (3)C21—C16—C17—C181.2 (5)
C9—N2—C8—S21.2 (5)C15—C16—C17—C18175.9 (3)
C7—N1—C8—N22.1 (5)C16—C17—C18—C191.4 (5)
C7—N1—C8—S2177.5 (3)C17—C18—C19—C200.9 (5)
C8—N2—C9—C1413.0 (5)C18—C19—C20—C210.2 (6)
C8—N2—C9—C10168.7 (3)C19—C20—C21—C160.1 (6)
C14—C9—C10—C110.1 (5)C17—C16—C21—C200.6 (5)
N2—C9—C10—C11178.3 (3)C15—C16—C21—C20176.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···S2i0.882.903.688 (4)150
N2—H1N2···O10.881.912.642 (3)140
N2—H1N2···S10.882.492.997 (3)117
C2—H2A···S2i0.952.773.556 (4)141
C6—H6···O10.952.432.760 (4)100
C14—H14···S20.952.503.184 (4)129
C15—H15A···O1ii0.992.393.366 (4)168
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC21H18N2OS2
Mr378.49
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)19.8574 (18), 4.9195 (5), 19.6197 (18)
β (°) 106.089 (2)
V3)1841.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.49 × 0.04 × 0.04
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.866, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
8509, 3231, 2488
Rint0.063
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.138, 1.11
No. of reflections3231
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.30

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996).

Selected bond lengths (Å) top
S2—C81.674 (3)N1—C81.401 (4)
O1—C71.230 (4)N2—C81.353 (4)
N1—C71.381 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···S2i0.882.8973.688 (4)150
N2—H1N2···O10.881.912.642 (3)140
N2—H1N2···S10.882.492.997 (3)117
C2—H2A···S2i0.952.773.556 (4)141
C6—H6···O10.952.432.760 (4)100
C14—H14···S20.952.503.184 (4)129
C15—H15A···O1ii0.992.393.366 (4)168
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
 

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