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The title compounds, 1,3-dibenzo­ylimidazolidine-2-thione, C17H14N2O2S, (I), and 1,3-dibenzo­yl-3,4,5,6-tetra­hydro­pyrimidine-2(1H)-thione, C18H16N2O2S, (II), were obtained from the reactions of imidazolidine-2-thione and 1,4,5,6-tetra­hydro­pyrimidine-2-thiol, respectively, with benzoyl chloride. Compounds (I) and (II) contain, respectively, imidazolidinethione [C=S = 1.6509 (14) Å] and ­pyrimidinethione [C=S = 1.6918 (19) Å] moieties bonded to two benzoyl rings. The mol­ecules of (I) exhibit C2 symmetry, the C=S bond lying along the twofold rotation axis, while the mol­ecules of (II) have mirror symmetry (Cs). The imida­zolidine ring in (I) is essentially planar, while the pyrimidine ring in (II) adopts a boat conformation. Mol­ecules of (I) are linked by weak inter­molecular C-H...O inter­actions, while mol­ecules of (II) are held together by van der Waals inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105009844/tr1118sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105009844/tr1118Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105009844/tr1118IIsup3.hkl
Contains datablock II

CCDC references: 275515; 275516

Comment top

Heterocyclic thioamides usually occurring in their thioketo form are referred to as `thiones'. Heterocyclic thiones have a wide range of applications as analytical reagents, as metal corrosion inhibitors and in the pharmaceutical field (Hussain et al., 1990). These compounds are of particular interest in coordination chemistry because they display both hard and soft donor sites. In many instances, heterocyclic thiones behave as polyfunctional ligands with monodentate, chelating and bridging coordination modes and form a wide range transition metal complexes, many of which have important chemical and biological properties (Raper, 1985, 1994, 1996, 1997; Akrivos, 2001). Furthermore, metal complexes of heterocyclic thiones exhibit interesting anticarcinogenic properties (Reedijk, 1992; van Boom & Reedijk, 1993; Barnham et al., 1994) and are used in the treatment of rheumatoid arthritis (Haynes & Whitehouse, 1989). Such complexes? are also used as models to understand the electronic and structural properties of the active sites in metalloenzymes (Casella et al., 1988; Gullotti, et al., 1989) and metal–DNA interactions (Tran Qui & Bagieu, 1990). In the course of synthesizing new ligands suitable for coordination chemistry, we prepared two new heterocyclic thiones, namely 1,3-dibenzoyl-4,5-dihydro-1H-imidazole-2-thione, C17H14N2O2S, (I), and 1,3-dibenzoyl-3,4,5,6-tetrahydropyrimidine-2(1H)-thione, C18H16N2O2S, (II), from the reactions of 4,5-dihydroimidazole-2(3H)-thione and 1,4,5,6-tetrahydropyrimidine-2-thiol, respectively, with benzoyl chloride.

Views of the molecules of (I) and (II), including the atom-numbering schemes, are shown in Figs. 1 and 2. Selected bond distances and angles are listed in Tables 1 and 2. Each compound exhibits a soft thione S donor and three hard donor sites (a carbonyl O and two N atoms) and seems to act as a chelating or a bridging ligand. These compounds are also interesting building blocks for generating coordination polymers upon metal complexation. Both (I) and (II) consist of thioimidazole and thiopyrimidine moieties bonded to two benzoyl rings. The thio substituents exist in the thione form. The C—S bond lengths in (I) and (II) are consistent with a double bond and are similar to those in other reported heterocyclic thione derivatives containing thioimidazole and thiopyrimidine cycles (Ozbey et al., 1991; Akkurt et al., 1992, 2000; Cox et al., 1996; Liu et al., 2003; Ozcelik et al., 2004; Brito et al., 2004). The C8—N1 bond distances in both compounds are intermediate between standard single C—N (1.47 Å) and double CN (1.28 Å) bonds, being significantly shorter than the C9—N1 bonds, because atom C8 is in an sp2 hybridized state, while atom C9 is sp3. The remaining bond lengths in both compounds show no unusual values.

The molecules of (I) show C2 symmetry, and the C8—S1 bond lies on the twofold rotation axis, while the molecules of (II) have mirror symmetry (Cs), with atoms S1, C8, C10, H10A and H10B situated on the mirror plane. The five-membered imidazole ring in (I) is essentially planar, with maximum deviations from the mean plane of −0.1418 (8) and 0.1397 (8) Å for atoms N1 and C9i [symmetry code: (i) 1 − x, 2 − y, z], respectively. The six-membered pyrimidine ring in (II) adopts a half-boat conformation, in which atoms C8 and C10 are displaced from the mean plane by 0.0387 (10) and 0.2561 (13) Å. The benzoyl rings in (I) make dihedral angles of 76.55 (3) and 79.85 (3)° with the mean plane of the imidazole ring. The dihedral angles between the two planar benzoyl fragments are 75.92 (3)° in (I) and 61.08 (4)° in (II). A non-planar disposition of the three rings in both compounds has been observed in other reported heterocyclic thione derivatives with similar fragments (Ozbey et al., 1991; Cox et al., 1996; Akkurt et al., 2000; Ozcelik et al., 2004).

The packing of the molecules in (I) and (II) is shown in Figs. 3 and 4. The molecules of (I) are linked by means of weak intermolecular C—H···O interactions (Table 1). Although there are no π···π stacking interactions in (II), the molecules are approximately paired, the two phenyl rings overlapping, forming channels running parallel to the a axis as shown in Fig 4. Examination of the structures with PLATON (Spek, 2003) indicates that there are no solvent-accesible voids in (I) and (II).

Experimental top

Triethylamine (TEA, 2.02 g, 20 mmol) was added to a solution of 4,5-dihydroimidazole-2(3H)-thione (1.02 g, 10 mmol) dissolved in THF (100 ml) with stirring on an ice bath for 30 min. Benzoyl chloride (2.81 g, 20 mmol) was added to the reaction mixture dropwise and it was refluxed for 4 h. The resulting solution was evaporated under vacuum to half the volume and then poured into ice water to precipitate. The residue was filtered off and single crystals of (I) suitable for X-ray measurements were obtained by crystallization from acetone. The procedure and molar quantities of the reactants for the preparation of (II) were the same as for (I), with 1,4,5,6-tetrahydropyrimidine-2-thiole replacing 4,5-dihydroimidazole-2(3H)-thione.

Refinement top

All H atoms were refined with a riding model [C—H = 0.95 and 0.99 Å, and Uiso(H) = 1.2 Ueq(C)].

Computing details top

For both compounds, data collection: COLLECT (Bruker, 2002); cell refinement: EVALCCD (Bruker, 2002); data reduction: EVALCCD; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecule of (I), showing the atom-labelling scheme (40% probability displacement ellipsoids).
[Figure 2] Fig. 2. The molecule of (II), showing the atom-labelling scheme (40% probability displacement ellipsoids).
[Figure 3] Fig. 3. A packing diagram of (I), viewed along the b axis.
[Figure 4] Fig. 4. A packing diagram of (II), viewed along the a axis.
(I) 1,3-Dibenzoyl-4,5-dihydro-1H-imidazole-2(3H)-thione top
Crystal data top
C17H14N2O2SF(000) = 324
Mr = 310.36Dx = 1.429 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 128 reflections
a = 11.8543 (8) Åθ = 6.0–20.0°
b = 5.7221 (2) ŵ = 0.23 mm1
c = 10.6312 (6) ÅT = 100 K
V = 721.13 (7) Å3Prism, yellow
Z = 20.37 × 0.16 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
1864 independent reflections
Radiation source: fine-focus sealed tube1772 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 9 pixels mm-1θmax = 28.7°, θmin = 3.4°
ϕ and ω scans with 2.0° and 80 s per frameh = 1616
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
k = 77
Tmin = 0.925, Tmax = 0.967l = 1414
21502 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)] = 0.024H-atom parameters constrained
wR(F2) = 0.059 w = 1/[σ2(Fo2) + (0.0278P)2 + 0.1874P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
1864 reflectionsΔρmax = 0.26 e Å3
101 parametersΔρmin = 0.19 e Å3
1 restraintAbsolute structure: Flack (1983), 757 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (6)
Crystal data top
C17H14N2O2SV = 721.13 (7) Å3
Mr = 310.36Z = 2
Orthorhombic, P21212Mo Kα radiation
a = 11.8543 (8) ŵ = 0.23 mm1
b = 5.7221 (2) ÅT = 100 K
c = 10.6312 (6) Å0.37 × 0.16 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
1864 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
1772 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.967Rint = 0.029
21502 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.059Δρmax = 0.26 e Å3
S = 1.09Δρmin = 0.19 e Å3
1864 reflectionsAbsolute structure: Flack (1983), 757 Friedel pairs
101 parametersAbsolute structure parameter: 0.03 (6)
1 restraint
Special details top

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
S10.50001.00000.68869 (3)0.01560 (10)
O10.35542 (8)0.50573 (19)0.94793 (8)0.02187 (19)
N10.43482 (8)0.86246 (17)0.92143 (9)0.0134 (2)
C10.22621 (9)0.93431 (19)0.76869 (11)0.0141 (2)
H1A0.24261.05720.82590.017*
C20.14397 (9)0.9638 (2)0.67731 (11)0.0158 (2)
H2A0.10231.10540.67330.019*
C30.12244 (10)0.7855 (2)0.59125 (12)0.0165 (2)
H3A0.06670.80680.52810.020*
C40.18194 (11)0.5772 (2)0.59733 (12)0.0173 (2)
H4A0.16780.45720.53760.021*
C50.26257 (10)0.54389 (19)0.69133 (11)0.0159 (2)
H5A0.30210.39990.69730.019*
C60.28466 (9)0.7233 (2)0.77616 (11)0.0131 (2)
C70.36160 (10)0.6815 (2)0.88443 (11)0.0144 (2)
C80.50001.00000.84393 (13)0.0121 (3)
C90.47107 (10)0.8805 (2)1.05407 (11)0.0157 (2)
H9A0.52430.75411.07680.019*
H9B0.40580.87721.11220.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01409 (17)0.02380 (19)0.00891 (16)0.00350 (16)0.0000.000
O10.0273 (4)0.0177 (4)0.0206 (4)0.0021 (4)0.0026 (3)0.0066 (4)
N10.0143 (5)0.0162 (5)0.0096 (4)0.0004 (4)0.0001 (4)0.0014 (4)
C10.0124 (5)0.0145 (5)0.0153 (5)0.0006 (4)0.0034 (4)0.0019 (4)
C20.0124 (5)0.0155 (6)0.0196 (5)0.0010 (4)0.0015 (4)0.0003 (5)
C30.0121 (5)0.0203 (6)0.0172 (6)0.0026 (4)0.0001 (4)0.0004 (5)
C40.0173 (5)0.0173 (5)0.0174 (5)0.0044 (4)0.0018 (4)0.0036 (5)
C50.0168 (5)0.0127 (5)0.0182 (5)0.0001 (4)0.0031 (4)0.0006 (5)
C60.0118 (5)0.0146 (5)0.0131 (5)0.0017 (4)0.0020 (4)0.0014 (4)
C70.0138 (5)0.0144 (5)0.0151 (5)0.0018 (4)0.0030 (4)0.0006 (4)
C80.0103 (6)0.0139 (6)0.0121 (5)0.0028 (6)0.0000.000
C90.0199 (6)0.0181 (6)0.0092 (5)0.0013 (5)0.0003 (4)0.0007 (4)
Geometric parameters (Å, º) top
N1—C71.4073 (15)C3—C41.3864 (17)
N1—C81.3766 (13)C3—H3A0.9500
N1—C91.4777 (15)C4—C51.3959 (17)
O1—C71.2135 (16)C4—H4A0.9500
S1—C81.6504 (14)C5—C61.3915 (16)
C1—C21.3866 (16)C5—H5A0.9500
C1—C61.3942 (15)C6—C71.4879 (17)
C1—H1A0.9500C9—C9i1.530 (2)
C2—C31.3940 (17)C9—H9A0.9900
C2—H2A0.9500C9—H9B0.9900
C7—N1—C9119.83 (9)C4—C5—H5A120.3
C8—N1—C7126.84 (10)C5—C6—C1120.56 (11)
C8—N1—C9111.59 (9)C5—C6—C7119.87 (10)
C2—C1—C6119.64 (11)C1—C6—C7119.21 (10)
C2—C1—H1A120.2O1—C7—N1119.45 (11)
C6—C1—H1A120.2O1—C7—C6121.78 (11)
C1—C2—C3119.97 (11)N1—C7—C6118.42 (10)
C1—C2—H2A120.0N1i—C8—N1106.48 (13)
C3—C2—H2A120.0N1i—C8—S1126.76 (6)
C4—C3—C2120.36 (11)N1—C8—S1126.76 (6)
C4—C3—H3A119.8N1—C9—C9i101.11 (6)
C2—C3—H3A119.8N1—C9—H9A111.5
C3—C4—C5119.93 (11)C9i—C9—H9A111.5
C3—C4—H4A120.0N1—C9—H9B111.5
C5—C4—H4A120.0C9i—C9—H9B111.5
C6—C5—C4119.49 (10)H9A—C9—H9B109.4
C6—C5—H5A120.3
C6—C1—C2—C31.87 (17)C9—N1—C7—C6151.18 (10)
C1—C2—C3—C40.76 (17)C5—C6—C7—O144.62 (17)
C2—C3—C4—C51.07 (18)C1—C6—C7—O1128.55 (12)
C3—C4—C5—C61.76 (18)C5—C6—C7—N1142.26 (11)
C4—C5—C6—C10.65 (17)C1—C6—C7—N144.56 (15)
C4—C5—C6—C7173.73 (11)C7—N1—C8—N1i174.60 (13)
C2—C1—C6—C51.17 (17)C9—N1—C8—N1i9.82 (6)
C2—C1—C6—C7171.95 (10)C7—N1—C8—S15.40 (13)
C8—N1—C7—O1141.55 (10)C9—N1—C8—S1170.18 (6)
C9—N1—C7—O122.10 (17)C8—N1—C9—C9i23.99 (13)
C8—N1—C7—C645.17 (15)C7—N1—C9—C9i170.02 (11)
Symmetry code: (i) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1ii0.992.473.2231 (16)132
Symmetry code: (ii) x+1, y+1, z.
(II) 1,3-Dibenzoyl-3,4,5,6-tetrahydropyrimidine-2(1H)-thione top
Crystal data top
C18H16N2O2SF(000) = 680
Mr = 324.39Dx = 1.382 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 150 reflections
a = 8.6803 (6) Åθ = 6.0–20.0°
b = 21.946 (1) ŵ = 0.22 mm1
c = 8.1845 (9) ÅT = 100 K
V = 1559.1 (2) Å3Irregular, colorless
Z = 40.23 × 0.23 × 0.16 mm
Data collection top
Nonius KappaCCD
diffractometer
2051 independent reflections
Radiation source: fine-focus sealed tube1707 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 9 pixels mm-1θmax = 28.7°, θmin = 3.4°
ϕ and ω scans with 1.4° and 126 s per frameh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
k = 2429
Tmin = 0.941, Tmax = 0.972l = 1111
22525 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0438P)2 + 0.7208P]
where P = (Fo2 + 2Fc2)/3
2051 reflections(Δ/σ)max = 0.001
109 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C18H16N2O2SV = 1559.1 (2) Å3
Mr = 324.39Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 8.6803 (6) ŵ = 0.22 mm1
b = 21.946 (1) ÅT = 100 K
c = 8.1845 (9) Å0.23 × 0.23 × 0.16 mm
Data collection top
Nonius KappaCCD
diffractometer
2051 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
1707 reflections with I > 2σ(I)
Tmin = 0.941, Tmax = 0.972Rint = 0.040
22525 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.09Δρmax = 0.32 e Å3
2051 reflectionsΔρmin = 0.28 e Å3
109 parameters
Special details top

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
S10.03972 (5)0.75000.05041 (6)0.01700 (13)
O10.18277 (15)0.61397 (5)0.15616 (13)0.0334 (3)
N10.30041 (13)0.69748 (5)0.04365 (13)0.0183 (2)
C10.27306 (16)0.63935 (7)0.26952 (17)0.0211 (3)
H1A0.32810.67650.25880.025*
C20.26144 (18)0.61116 (8)0.42084 (18)0.0302 (4)
H2A0.30880.62910.51380.036*
C30.1815 (2)0.55730 (8)0.4367 (2)0.0378 (4)
H3A0.17290.53850.54080.045*
C40.1137 (2)0.53055 (8)0.3019 (2)0.0398 (5)
H4A0.05980.49310.31350.048*
C50.12401 (18)0.55813 (7)0.1492 (2)0.0274 (3)
H5A0.07710.53980.05660.033*
C60.20375 (15)0.61295 (6)0.13345 (16)0.0177 (3)
C70.21906 (16)0.63974 (6)0.03214 (16)0.0192 (3)
C80.2246 (2)0.75000.0151 (2)0.0157 (4)
C90.45417 (16)0.69417 (7)0.12014 (19)0.0257 (3)
H9A0.44350.69200.24040.031*
H9B0.50850.65710.08250.031*
C100.5456 (2)0.75000.0738 (3)0.0266 (5)
H10A0.64570.75000.13170.032*
H10B0.56590.75000.04520.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0152 (2)0.0180 (2)0.0179 (2)0.0000.00326 (17)0.000
O10.0498 (7)0.0282 (6)0.0221 (6)0.0020 (5)0.0116 (5)0.0064 (4)
N10.0172 (5)0.0197 (6)0.0179 (5)0.0024 (4)0.0043 (4)0.0013 (4)
C10.0194 (6)0.0248 (7)0.0191 (6)0.0018 (5)0.0006 (5)0.0012 (5)
C20.0272 (8)0.0447 (10)0.0188 (7)0.0115 (7)0.0016 (6)0.0061 (7)
C30.0376 (9)0.0412 (10)0.0345 (9)0.0170 (8)0.0159 (7)0.0198 (8)
C40.0354 (9)0.0226 (8)0.0614 (12)0.0027 (7)0.0191 (8)0.0148 (8)
C50.0239 (7)0.0187 (7)0.0398 (9)0.0006 (6)0.0026 (6)0.0020 (6)
C60.0152 (6)0.0170 (6)0.0209 (6)0.0038 (5)0.0005 (5)0.0009 (5)
C70.0210 (6)0.0168 (6)0.0197 (6)0.0043 (5)0.0035 (5)0.0017 (5)
C80.0176 (8)0.0190 (9)0.0104 (8)0.0000.0006 (7)0.000
C90.0190 (7)0.0310 (8)0.0271 (7)0.0061 (6)0.0066 (6)0.0019 (6)
C100.0159 (9)0.0409 (12)0.0231 (10)0.0000.0017 (8)0.000
Geometric parameters (Å, º) top
N1—C71.4537 (18)C3—H3A0.9500
N1—C81.3478 (15)C4—C51.391 (2)
N1—C91.4760 (17)C4—H4A0.9500
O1—C71.2039 (17)C5—C61.394 (2)
S1—C81.6918 (19)C5—H5A0.9500
C1—C21.388 (2)C6—C71.4832 (19)
C1—C61.3920 (19)C9—C101.5082 (19)
C1—H1A0.9500C9—H9A0.9900
C2—C31.377 (3)C9—H9B0.9900
C2—H2A0.9500C10—H10A0.9900
C3—C41.381 (3)C10—H10B0.9900
C7—N1—C9115.08 (11)C1—C6—C7121.82 (13)
C8—N1—C7119.80 (12)C5—C6—C7118.11 (13)
C8—N1—C9123.87 (12)O1—C7—N1118.82 (13)
C2—C1—C6119.79 (14)O1—C7—C6124.10 (13)
C2—C1—H1A120.1N1—C7—C6116.63 (11)
C6—C1—H1A120.1N1i—C8—N1117.56 (16)
C3—C2—C1120.21 (16)N1—C8—S1121.21 (8)
C3—C2—H2A119.9N1—C9—C10109.21 (13)
C1—C2—H2A119.9N1—C9—H9A109.8
C2—C3—C4120.30 (15)C10—C9—H9A109.8
C2—C3—H3A119.8N1—C9—H9B109.8
C4—C3—H3A119.8C10—C9—H9B109.8
C3—C4—C5120.32 (15)H9A—C9—H9B108.3
C3—C4—H4A119.8C9—C10—C9i108.66 (17)
C5—C4—H4A119.8C9—C10—H10A110.0
C4—C5—C6119.38 (15)C9i—C10—H10A110.0
C4—C5—H5A120.3C9—C10—H10B110.0
C6—C5—H5A120.3C9i—C10—H10B110.0
C1—C6—C5119.98 (13)H10A—C10—H10B108.3
C6—C1—C2—C30.1 (2)C1—C6—C7—O1167.71 (14)
C1—C2—C3—C40.7 (2)C5—C6—C7—O18.9 (2)
C2—C3—C4—C50.8 (2)C1—C6—C7—N14.47 (19)
C3—C4—C5—C60.2 (2)C5—C6—C7—N1178.89 (12)
C2—C1—C6—C50.5 (2)C7—N1—C8—N1i173.28 (10)
C2—C1—C6—C7177.07 (13)C9—N1—C8—N1i6.7 (2)
C4—C5—C6—C10.5 (2)C7—N1—C8—S15.5 (2)
C4—C5—C6—C7177.16 (13)C9—N1—C8—S1172.02 (11)
C8—N1—C7—O1103.75 (17)C8—N1—C9—C1032.02 (19)
C9—N1—C7—O163.95 (17)C7—N1—C9—C10160.84 (12)
C8—N1—C7—C683.64 (16)N1—C9—C10—C9i54.9 (2)
C9—N1—C7—C6108.66 (13)
Symmetry code: (i) x, y+3/2, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC17H14N2O2SC18H16N2O2S
Mr310.36324.39
Crystal system, space groupOrthorhombic, P21212Orthorhombic, Pnma
Temperature (K)100100
a, b, c (Å)11.8543 (8), 5.7221 (2), 10.6312 (6)8.6803 (6), 21.946 (1), 8.1845 (9)
V3)721.13 (7)1559.1 (2)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.230.22
Crystal size (mm)0.37 × 0.16 × 0.120.23 × 0.23 × 0.16
Data collection
DiffractometerNonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Multi-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.925, 0.9670.941, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
21502, 1864, 1772 22525, 2051, 1707
Rint0.0290.040
(sin θ/λ)max1)0.6750.675
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.059, 1.09 0.038, 0.095, 1.09
No. of reflections18642051
No. of parameters101109
No. of restraints10
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.190.32, 0.28
Absolute structureFlack (1983), 757 Friedel pairs?
Absolute structure parameter0.03 (6)?

Computer programs: COLLECT (Bruker, 2002), EVALCCD (Bruker, 2002), EVALCCD, SHELXTL (Bruker, 2002), SHELXTL.

Selected geometric parameters (Å, º) for (I) top
N1—C71.4073 (15)O1—C71.2135 (16)
N1—C81.3766 (13)S1—C81.6504 (14)
N1—C91.4777 (15)C9—C9i1.530 (2)
C7—N1—C9119.83 (9)N1i—C8—N1106.48 (13)
C8—N1—C7126.84 (10)N1—C8—S1126.76 (6)
C8—N1—C9111.59 (9)
C9—N1—C8—N1i9.82 (6)C8—N1—C9—C9i23.99 (13)
C9—N1—C8—S1170.18 (6)C7—N1—C9—C9i170.02 (11)
Symmetry code: (i) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1ii0.992.473.2231 (16)132
Symmetry code: (ii) x+1, y+1, z.
Selected geometric parameters (Å, º) for (II) top
N1—C71.4537 (18)O1—C71.2039 (17)
N1—C81.3478 (15)S1—C81.6918 (19)
N1—C91.4760 (17)C9—C101.5082 (19)
C7—N1—C9115.08 (11)N1i—C8—N1117.56 (16)
C8—N1—C7119.80 (12)N1—C8—S1121.21 (8)
C8—N1—C9123.87 (12)
C7—N1—C8—N1i173.28 (10)C8—N1—C9—C1032.02 (19)
C9—N1—C8—N1i6.7 (2)N1—C9—C10—C9i54.9 (2)
C9—N1—C8—S1172.02 (11)
Symmetry code: (i) x, y+3/2, z.
 

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