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In the crystal structure of the title compound, C20H18N2O2S, mol­ecules are linked by bifurcated C—H...O hydrogen-bond inter­actions, giving rise to chains whose links are composed of alternating centrosymmetrically disposed pairs of molecules and characterized by R22(10) and R22(20) hydrogen-bonding motifs. Also, N—H...S hydrogen bonds form infinite zigzag chains along the [010] direction, which exhibit the C(4) motif. Hirshfeld surface and fingerprint plots were used to explore the inter­molecular inter­actions in the crystal structure. This analysis confirms the important role of C—H...O hydrogen bonds in the mol­ecular conformation and in the crystal structure, providing a potentially useful tool for a full understanding of the inter­molecular inter­actions in acyl­thio­urea derivatives.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111052620/fa3263sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111052620/fa3263Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111052620/fa3263Isup3.cml
Supplementary material

CCDC reference: 866757

Comment top

In recent years, acylthiourea derivatives have been extensively studied and many biological activities attributed to them, such as pesticidal, fungicidal, antiviral and plant-growth regulatory activities (Hernández et al., 2003). N-Acyl-N',N'-disubstituted thiourea derivatives have also attracted considerable attention because of their coordination ability with transition metal ions (Binzet et al., 2009). Recently, we have begun to study a novel series of N-acyl-N',N'-disubstituted thiourea derivatives and their complexes with transition metals (Pérez, Corrêa, Duque et al., 2008; Pérez, Mascarenhas et al., 2008; Pérez, Corrêa, Plutín et al., 2008; Pérez et al., 2009).

One of these derivatives is the title compound, (I) (Fig. 1). The C2—S1 and C1—O1 bonds have lengths indicating double-bond character, whereas the C—N bonds are single (Table 1). The conformation of the molecule with respect to the thiocarbonyl and carbonyl groups is twisted, as reflected by the C1—N1—C2—N2 and S1—C2—N1—C1 torsion angles (Table 1). As the thiourea and acyl units are not coplanar and the bond lengths do not present significant C2—S1 and C1—O1 lengthening or C—N shortening, resonance effects are absent in this part of the molecule. For related compounds, it has been observed that the resonance effect involving the acylthiourea moiety is only present when there is a proton linked to N2 (Corrêa et al., 2008; Estévez-Hernández et al., 2008). As atom N2 is fully substituted in (I), this effect is not active.

In the crystal structure, molecules of (I) are linked into infinite C4 (Bernstein et al., 1995) zigzag chains along [010] by N—H···S hydrogen bonds (Fig. 2). A search of the Cambridge Structural Database (CSD; Version 5.32, update of November 2011; Allen, 2002) for organic acylthiourea substructures revealed 440 such crystal structures. Some 236 of these structures exhibit a characteristic intermolecular pattern, forming dimers via N—H···S hydrogen bonding to give an eight-membered R22(8) ring (Shanmuga Sundara Raj et al., 1999; Corrêa et al., 2008; Gomes et al., 2010). An interesting acceptor-bifurcated intermolecular interaction is observed in (I), involving carbonyl atom O1 and forming an H4···O1···H17 angle of 76.3°. In this contact, the furoyl C4—H4 fragment at (-x + 2, -y + 1, z) is linked to atom O1, forming an R22(10) centrosymmetric dimer (Fig. 3), whereas in the second interaction, atom O1 acts as acceptor from the C17—H17 group at (-x + 1, -y, -z), forming an R22(20) centrosymmetric dimer (Fig. 3). The latter contact plays a role in establishing and stabilizing the conformation of the C15–C20 ring. In thiourea derivatives, these structural motifs, ten- and 20-membered rings mediated by C—H···O hydrogen bonding, are unexpected. Furthermore, there is no indication in (I) of any intermolecular hydrogen bonding between the NH group and the O atom of the furan ring. As a result, the packing in (I) comprises a network of hydrogen bonds and noncovalent contacts (Table 2) forming alternating hydrophilic and hydrophobic regions along the [100] direction (Fig. 4). This pattern of hydrogen bonds is not common in related structures, which prompted us to explore the contributions of the main intermolecular contacts in the crystal packing of (I), as well as the importance of C—H···O nonclassical hydrogen bonding in establishing the organization of the extended structure.

Van der Waals interactions (H···H, C···H, S···H, N···H and O···H) are also present in this structure. The main intermolecular interactions in (I) were analysed using the Hirshfeld surface (McKinnon et al., 1998) and the corresponding two-dimensional fingerprint plots (Spackman & Jayatilaka, 2009; McKinnon et al., 2007). Hirshfeld surfaces and their two-dimensional fingerprints are useful tools for visualizing and analysing structural properties in relation to packing patterns. Intermolecular interactions present in the structure of a molecular crystal are depicted by the construction of the two-dimensional fingerprint graphic, which is a frequency plot of (de, di) pairs, in which de is the distance from a point on the Hirshfeld surface to the nearest external atom and di is the distance from the same point on the Hirshfeld surface to the nearest atom internal to the surface. The relative frequency of occurrence of a (de, di) pair, represented by colours in the fingerprint plot, is an indication of the importance of a particular type of interaction in the crystal structure being examined. As described by Spackman & Jayatilaka (2009), different types of common non-covalent interactions give characteristic patterns in the fingerprint plots. In the two-dimensional diagrams depicted for (I) in Fig. 5, we can identify and compare the types of intermolecular interactions present. Fig. 5(a) isolates H···H contacts and shows spikes centred near a (de + di) sum of 2.4 Å [H6···H12i = 2.49 Å; symmetry code: (i) x + 1, y + 1, z)], whereas Fig 5(b), isolating C···H contacts, shows spikes centred around (de + di) of 2.9 Å [C1···H12i, C12···H6ii and C19···H7Biii are 3.03, 2.99 and 3.09 Å, respectively; symmetry codes: (i) x + 1, y, z; (ii) x - 1, y - 1, z; (iii) x, y - 1, z]. In addition, Figs. 5(c) and 5(d) (S···H and O···H, respectively) show much sharper spikes, revealing specific N—H···S and C—H···O hydrogen bonds with spikes centred around (de + di) sums of 2.6 and 2.4 Å, respectively. These two values indicate that the C—H···O hydrogen bond is the stronger interaction. The relative contributions to the Hirshfeld surface area due to H···H, C···H, S···H, O···H and N···H contacts for (I) are 49.2, 23.4, 12.6, 11.4 and 0.3%, respectively. For the intermolecular contacts, the smallest fingerprint contributions occur for O···S (0.5%) and C···S (0.1%). Also, it is clear that the presence of a network of nonclassical C—H···O contacts exerts an important influence on the stabilization of the packing in (I).

The results reported here underline the utility of Hirshfeld surfaces and fingerprint-plot analysis for a full understanding of the intermolecular contacts in acylthiourea derivatives.

Related literature top

For related literature, see: Allen (2002); Bernstein et al. (1995); Binzet et al. (2009); Corrêa et al. (2008); Estévez-Hernández, Duque, Ellena & Corrêa (2008); Gomes et al. (2010); Hernández et al. (2003); McKinnon et al. (1998, 2007); Nagasawa & Mitsunobu (1981); Pérez et al. (2009); Pérez, Corrêa, Duque, Plutín & O'Reilly (2008); Pérez, Corrêa, Plutín, O'Reilly & Duque (2008); Pérez, Mascarenhas, Plutín, de Souza Corrêa & Duque (2008); Shanmuga Sundara Raj, Puviarasan, Velmurugan, Jayanthi & Fun (1999); Spackman & Jayatilaka (2009).

Experimental top

The title compound was prepared using the standard procedure previously reported in the literature (Nagasawa & Mitsunobu, 1981) by the reaction of furoyl chloride with KSCN in anhydrous acetone, and then condensation with dibenzylamine. The reaction mixture was poured into cold water, resulting in precipitation of the solid product. Recrystallization from acetone–water solution (1:1 v/v) yielded colourless crystals of (I) (2.7 g, 9.0 mmol, 90%; m.p. 419 K). Spectroscopic analysis: IR (KBr, ν, cm-1): 3320 (free NH), 3200 (assoc. NH), 1693 (CO), 1608 (arom.), 1580 (thioureido I), 1425 II, 1173 III, 1025 (C5—O—C8), 928 IV; 1H NMR (CDCl3, δ, p.p.m.): 8.71 (1H, s, broad NH), 7.63 (1H, s, H8, J = 2.1 Hz), 7.52–7.32 (10H, m, Ph), 7.10 (1H, s, H6, J = 3.2 Hz), 6.60–6.50 (1H, m, H7), 5.20 (2H, s, CH2), 4.72 (2H, s, CH2); 13C NMR (CDCl3, δ, p.p.m.): 189.8 (CS), 153.9 (CO), 147.6 (C5), 145.5 (C8), 138.4 (1 C—Ph), 136.9 (1 C—Ph), 129.1 (2 C—Ph), 128.8 (2 C—Ph), 128.5 (3 C—Ph), 128.4 (3 C—Ph), 127.7 (4 C—Ph), 127.5 (4 C—Ph), 117.6 (C6), 112.9 (C7), 56.1 (CH2), 55.3 (CH2). EIMS m/e: 350 (20), 95 (100), 91 (84), 65 (31), 39 (6). Analysis, calculated for C20H18N2O2S: C 68.55, H 5.17, N 7.95, S 9.15%; found: C 68.12, H 5.14, N 8.15, S 9.19%.

Refinement top

H atoms were treated as riding, with aromatic C—H = 0.93 Å and CH2 C—H = 0.97 Å, and with Uiso(H) = 1.2Ueq(C). The N-bound H atom was located by difference Fourier synthesis and its position was fixed as initially found, with Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: COLLECT (Enraf–Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), Mercury (Macrae et al., 2008) and CrystalExplorer (Wolff et al., 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of (I), showing intermolecular N—H···S hydrogen bonds (dashed lines) forming an infinite C4 zigzag chain along the [010] direction. [Symmetry codes: (v) 2 - x, -1/2 + y, 1/2 - z; (vi) x, -1 + y, z.]
[Figure 3] Fig. 3. A representation of the molecules of (I) connected by non-classical C—H···O hydrogen bonding (dashed lines). [Symmetry codes: (i) 2 - x, -y, -z; (ii) 2 - x, 1 - y, -z.]
[Figure 4] Fig. 4. A packing diagram for (I), showing the alternating hydrophilic and hydrophobic regions along the [100] direction.
[Figure 5] Fig. 5. Fingerprint plots of (I) resolved into (a) H···H, (b) C···H, (c) S···H and (d) O···H intermolecular contacts. The full fingerprint appears beneath each decomposed plot as a grey shadow.
N,N-dibenzyl-N'-(furan-2-carbonyl)thiourea top
Crystal data top
C20H18N2O2SF(000) = 736
Mr = 350.42Dx = 1.269 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 18661 reflections
a = 10.0449 (2) Åθ = 2.9–27.5°
b = 7.5527 (1) ŵ = 0.19 mm1
c = 24.3945 (5) ÅT = 294 K
β = 97.538 (1)°Prism, colourless
V = 1834.72 (6) Å30.23 × 0.21 × 0.09 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
4061 independent reflections
Radiation source: Enraf Nonius FR5902616 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.2°
CCD rotation images, thick slices scansh = 129
Absorption correction: gaussian
(based on crystal morphology; Coppens et al., 1965)
k = 99
Tmin = 0.959, Tmax = 0.983l = 3131
11569 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0578P)2 + 0.191P]
where P = (Fo2 + 2Fc2)/3
4061 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C20H18N2O2SV = 1834.72 (6) Å3
Mr = 350.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0449 (2) ŵ = 0.19 mm1
b = 7.5527 (1) ÅT = 294 K
c = 24.3945 (5) Å0.23 × 0.21 × 0.09 mm
β = 97.538 (1)°
Data collection top
Nonius KappaCCD
diffractometer
4061 independent reflections
Absorption correction: gaussian
(based on crystal morphology; Coppens et al., 1965)
2616 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.983Rint = 0.038
11569 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.04Δρmax = 0.13 e Å3
4061 reflectionsΔρmin = 0.21 e Å3
226 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C11.03450 (16)0.4444 (2)0.10816 (7)0.0529 (4)
C20.95953 (15)0.2518 (2)0.17915 (6)0.0483 (4)
C31.11098 (17)0.6053 (2)0.10191 (7)0.0545 (4)
C41.1566 (2)0.6799 (3)0.05781 (8)0.0700 (5)
H41.14520.63750.02170.084*
C51.2251 (2)0.8356 (3)0.07741 (10)0.0864 (7)
H51.26770.91570.05660.104*
C61.2169 (3)0.8458 (3)0.13116 (11)0.0920 (7)
H61.25410.93610.15420.11*
C70.74346 (17)0.2952 (3)0.11883 (7)0.0624 (5)
H7A0.71940.23680.08350.075*
H7B0.78190.40960.11190.075*
C80.61934 (17)0.3213 (2)0.14655 (7)0.0582 (4)
C90.6249 (2)0.4115 (3)0.19596 (9)0.0799 (6)
H90.70710.45310.21310.096*
C100.5104 (2)0.4411 (4)0.22045 (10)0.0932 (7)
H100.51590.50230.25380.112*
C110.3893 (2)0.3805 (3)0.19575 (11)0.0904 (7)
H110.31210.40060.21210.109*
C120.38173 (19)0.2911 (3)0.14748 (11)0.0816 (6)
H120.2990.24940.13090.098*
C130.49593 (18)0.2607 (3)0.12219 (9)0.0692 (5)
H130.48920.19950.08890.083*
C140.80012 (18)0.0082 (2)0.16659 (7)0.0629 (5)
H14A0.72750.01710.1890.075*
H14B0.8740.05330.18820.075*
C150.75309 (18)0.0988 (2)0.11559 (7)0.0577 (4)
C160.8322 (2)0.1175 (3)0.07395 (8)0.0763 (6)
H160.91430.05920.07620.092*
C170.7896 (3)0.2234 (4)0.02866 (9)0.0959 (7)
H170.84310.2360.00050.115*
C180.6687 (3)0.3095 (3)0.02523 (11)0.1004 (9)
H180.64080.38140.00510.12*
C190.5896 (3)0.2905 (3)0.06579 (12)0.0941 (7)
H190.50710.3480.0630.113*
C200.6313 (2)0.1859 (3)0.11113 (9)0.0740 (5)
H200.5770.1740.1390.089*
N11.00097 (13)0.41714 (17)0.16030 (5)0.0510 (3)
H11.03910.49020.18950.061*
N20.84419 (14)0.18744 (17)0.15376 (5)0.0541 (4)
O11.00404 (14)0.34197 (17)0.07019 (5)0.0715 (4)
O21.14685 (14)0.70610 (17)0.14798 (5)0.0741 (4)
S11.05719 (5)0.15666 (6)0.231130 (18)0.06310 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0556 (10)0.0609 (10)0.0429 (9)0.0007 (8)0.0089 (7)0.0016 (8)
C20.0538 (9)0.0525 (9)0.0399 (8)0.0020 (7)0.0107 (7)0.0013 (7)
C30.0558 (10)0.0588 (10)0.0497 (10)0.0010 (8)0.0099 (8)0.0024 (8)
C40.0767 (13)0.0769 (14)0.0586 (11)0.0038 (10)0.0169 (10)0.0082 (9)
C50.0931 (16)0.0760 (14)0.0936 (17)0.0178 (12)0.0255 (13)0.0166 (12)
C60.1121 (19)0.0731 (14)0.0923 (17)0.0351 (13)0.0200 (14)0.0006 (12)
C70.0563 (10)0.0730 (12)0.0555 (10)0.0013 (9)0.0013 (8)0.0162 (9)
C80.0510 (10)0.0626 (11)0.0587 (10)0.0033 (8)0.0013 (8)0.0080 (8)
C90.0617 (12)0.1020 (16)0.0738 (13)0.0152 (11)0.0005 (10)0.0101 (12)
C100.0822 (16)0.1139 (19)0.0851 (15)0.0006 (14)0.0170 (13)0.0178 (14)
C110.0633 (14)0.1029 (18)0.1074 (19)0.0072 (12)0.0199 (13)0.0064 (15)
C120.0490 (11)0.0783 (14)0.1144 (19)0.0026 (10)0.0009 (11)0.0075 (13)
C130.0598 (11)0.0641 (11)0.0792 (13)0.0008 (9)0.0082 (9)0.0019 (10)
C140.0690 (11)0.0622 (11)0.0565 (10)0.0107 (9)0.0051 (8)0.0105 (9)
C150.0565 (10)0.0572 (10)0.0580 (10)0.0030 (8)0.0025 (8)0.0080 (8)
C160.0709 (13)0.0886 (15)0.0701 (13)0.0067 (10)0.0126 (10)0.0002 (11)
C170.126 (2)0.0963 (17)0.0671 (14)0.0294 (17)0.0197 (14)0.0037 (13)
C180.134 (2)0.0694 (15)0.0864 (18)0.0148 (15)0.0287 (17)0.0125 (13)
C190.0880 (17)0.0718 (15)0.114 (2)0.0088 (12)0.0181 (15)0.0072 (14)
C200.0671 (12)0.0649 (12)0.0895 (15)0.0076 (10)0.0085 (10)0.0009 (11)
N10.0627 (8)0.0521 (8)0.0386 (7)0.0057 (6)0.0078 (6)0.0003 (6)
N20.0539 (8)0.0576 (8)0.0497 (8)0.0019 (6)0.0030 (6)0.0109 (6)
O10.0934 (10)0.0765 (9)0.0475 (7)0.0183 (7)0.0208 (6)0.0115 (6)
O20.0931 (10)0.0692 (8)0.0612 (8)0.0212 (7)0.0153 (7)0.0029 (6)
S10.0644 (3)0.0675 (3)0.0543 (3)0.0001 (2)0.0040 (2)0.0111 (2)
Geometric parameters (Å, º) top
C1—O11.2147 (19)C10—H100.93
C1—N11.373 (2)C11—C121.351 (3)
C1—C31.457 (2)C11—H110.93
C2—N21.332 (2)C12—C131.391 (3)
C2—N11.412 (2)C12—H120.93
C2—S11.6614 (16)C13—H130.93
C3—C41.346 (2)C14—N21.470 (2)
C3—O21.366 (2)C14—C151.507 (2)
C4—C51.414 (3)C14—H14A0.97
C4—H40.93C14—H14B0.97
C5—C61.327 (3)C15—C161.377 (3)
C5—H50.93C15—C201.380 (3)
C6—O21.361 (2)C16—C171.385 (3)
C6—H60.93C16—H160.93
C7—N21.479 (2)C17—C181.371 (4)
C7—C81.507 (3)C17—H170.93
C7—H7A0.97C18—C191.356 (4)
C7—H7B0.97C18—H180.93
C8—C91.379 (3)C19—C201.379 (3)
C8—C131.381 (2)C19—H190.93
C9—C101.382 (3)C20—H200.93
C9—H90.93N1—H10.9423
C10—C111.364 (3)
O1—C1—N1122.88 (15)C11—C12—H12119.5
O1—C1—C3122.36 (15)C13—C12—H12119.5
N1—C1—C3114.76 (15)C8—C13—C12120.0 (2)
N2—C2—N1116.55 (13)C8—C13—H13120
N2—C2—S1125.97 (13)C12—C13—H13120
N1—C2—S1117.48 (11)N2—C14—C15112.89 (14)
C4—C3—O2110.10 (16)N2—C14—H14A109
C4—C3—C1132.21 (17)C15—C14—H14A109
O2—C3—C1117.69 (14)N2—C14—H14B109
C3—C4—C5106.21 (18)C15—C14—H14B109
C3—C4—H4126.9H14A—C14—H14B107.8
C5—C4—H4126.9C16—C15—C20118.96 (18)
C6—C5—C4106.98 (18)C16—C15—C14121.02 (17)
C6—C5—H5126.5C20—C15—C14119.96 (17)
C4—C5—H5126.5C15—C16—C17120.0 (2)
C5—C6—O2110.8 (2)C15—C16—H16120
C5—C6—H6124.6C17—C16—H16120
O2—C6—H6124.6C18—C17—C16120.1 (2)
N2—C7—C8110.91 (14)C18—C17—H17120
N2—C7—H7A109.5C16—C17—H17120
C8—C7—H7A109.5C19—C18—C17120.3 (2)
N2—C7—H7B109.5C19—C18—H18119.8
C8—C7—H7B109.5C17—C18—H18119.8
H7A—C7—H7B108C18—C19—C20120.0 (2)
C9—C8—C13118.11 (18)C18—C19—H19120
C9—C8—C7121.02 (16)C20—C19—H19120
C13—C8—C7120.83 (17)C19—C20—C15120.6 (2)
C8—C9—C10121.12 (19)C19—C20—H20119.7
C8—C9—H9119.4C15—C20—H20119.7
C10—C9—H9119.4C1—N1—C2123.56 (13)
C11—C10—C9120.0 (2)C1—N1—H1119.2
C11—C10—H10120C2—N1—H1112.3
C9—C10—H10120C2—N2—C14120.33 (13)
C12—C11—C10119.9 (2)C2—N2—C7123.68 (14)
C12—C11—H11120.1C14—N2—C7115.28 (14)
C10—C11—H11120.1C6—O2—C3105.95 (16)
C11—C12—C13120.91 (19)
O1—C1—C3—C43.7 (3)C15—C16—C17—C180.0 (3)
N1—C1—C3—C4176.92 (18)C16—C17—C18—C190.6 (4)
O1—C1—C3—O2176.19 (16)C17—C18—C19—C200.9 (4)
N1—C1—C3—O23.2 (2)C18—C19—C20—C150.5 (3)
O2—C3—C4—C50.2 (2)C16—C15—C20—C190.2 (3)
C1—C3—C4—C5179.72 (18)C14—C15—C20—C19177.23 (18)
C3—C4—C5—C60.0 (3)O1—C1—N1—C216.7 (3)
C4—C5—C6—O20.1 (3)C3—C1—N1—C2162.70 (14)
N2—C7—C8—C963.1 (2)N2—C2—N1—C164.7 (2)
N2—C7—C8—C13119.13 (18)S1—C2—N1—C1116.05 (15)
C13—C8—C9—C100.2 (3)N1—C2—N2—C14173.61 (14)
C7—C8—C9—C10177.6 (2)S1—C2—N2—C147.2 (2)
C8—C9—C10—C110.1 (4)N1—C2—N2—C716.5 (2)
C9—C10—C11—C120.2 (4)S1—C2—N2—C7162.74 (13)
C10—C11—C12—C130.4 (4)C15—C14—N2—C2133.05 (16)
C9—C8—C13—C120.0 (3)C15—C14—N2—C756.2 (2)
C7—C8—C13—C12177.85 (18)C8—C7—N2—C2110.02 (18)
C11—C12—C13—C80.3 (3)C8—C7—N2—C1460.4 (2)
N2—C14—C15—C1652.4 (2)C5—C6—O2—C30.2 (3)
N2—C14—C15—C20130.28 (18)C4—C3—O2—C60.3 (2)
C20—C15—C16—C170.4 (3)C1—C3—O2—C6179.65 (17)
C14—C15—C16—C17176.98 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.942.272.668 (2)105
N1—H1···S1i0.942.603.322 (2)134
C4—H4···O1ii0.932.533.325 (2)143
C7—H7B···N10.972.362.806 (2)107
C14—H14B···S10.972.553.056 (2)113
C17—H17···O1iii0.932.583.496 (3)167
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x+2, y+1, z; (iii) x+2, y, z.

Experimental details

Crystal data
Chemical formulaC20H18N2O2S
Mr350.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)10.0449 (2), 7.5527 (1), 24.3945 (5)
β (°) 97.538 (1)
V3)1834.72 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.23 × 0.21 × 0.09
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionGaussian
(based on crystal morphology; Coppens et al., 1965)
Tmin, Tmax0.959, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
11569, 4061, 2616
Rint0.038
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.124, 1.04
No. of reflections4061
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.21

Computer programs: COLLECT (Enraf–Nonius, 2000), SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997) and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), Mercury (Macrae et al., 2008) and CrystalExplorer (Wolff et al., 2005), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
C1—O11.2147 (19)C2—S11.6614 (16)
C1—N11.373 (2)C7—N21.479 (2)
C2—N21.332 (2)C14—N21.470 (2)
C2—N11.412 (2)
N2—C2—N1—C164.7 (2)S1—C2—N1—C1116.05 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.942.272.668 (2)105
N1—H1···S1i0.942.603.322 (2)134
C4—H4···O1ii0.932.533.325 (2)143
C7—H7B···N10.972.362.806 (2)107
C14—H14B···S10.972.553.056 (2)113
C17—H17···O1iii0.932.583.496 (3)167
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x+2, y+1, z; (iii) x+2, y, z.
 

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