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In the mol­ecule of the title compound, C25H21N3OS, which was prepared by mild oxidation of the corresponding 5,6,7,8,9,10-hexa­hydro analogue, the fused carbocyclic ring adopts an envelope conformation. Pairs of mol­ecules are linked into cyclic centrosymmetric dimers by pairs of inversion-related N-H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011303059X/sk3519sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827011303059X/sk3519Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S010827011303059X/sk3519Isup3.cml
Supplementary material

CCDC reference: 970789

Introduction top

We report here the molecular and supra­molecular structure of the title compound (9E)-9-benzyl­idene-2-methyl­sulfanyl-5-phenyl-6,7,8,9-tetra­hydro­pyrimido[4,5-b]quinolin-4(3H)-one, (I) (Fig. 1), which we compare with the related reduced compound, (II) (see Scheme 1; Becerra et al., 2010). Compounds containing a pyrimido­quinoline framework have attracted considerable inter­est in recent years because of the wide range of biological activity which they can exhibit. For example, compounds of this type have been found to exhibit anti­bacterial activity against Escherischia coli and Pseudomonas aeruginosa (Selvi et al., 2006) and anti­fungal activity against Candida albicans and Candida gabrata (El-Gazzar et al., 2008), as well as acting as potent inhibitors of Ehrlich Ascites Carconoma (EAC) cells (Alqasoumi et al., 2010), in addition to potential anti­malarial activity (Joshi & Viswanathan, 2006). During our studies on the use of bis-aryl­idene derivatives for the synthesis of a range of heterocyclic frameworks (Becerra et al., 2010; Insuasty et al., 2008, 2013a,b), pyrimido[4,5-b]quinolines have proved to be inter­esting targets because of their structural resemblance to benzopteridine derivatives. The title compound, (I), is an example of this class and it was prepared by mild oxidation, using p-chloranil (2,3,5,6-tetra­chloro-1,4-benzo­quinone), of the corresponding 5,6,7,8,9,10-hexa­hydro derivative [cf. compound (II)], which had itself been prepared by the acid-catalysed condensation reaction between (2E,6E)-2,6-di­benzyl­idene­cyclo­hexanone and 6-amino-2-methyl­sulfanylpyrimidin-4(3H)-one (cf. Becerra et al., 2010).

Experimental top

Synthesis and crystallization top

A mixture of (9E)-9-benzyl­idene-2-methyl­sulfanyl-5-phenyl-5,6,7,8,9,10-hexa­hydro­pyrimido[4,5-b]quinolin-4(3H)-one (1 mmol) and p-chloranil (1 mmol) in chloro­form (20 ml) was heated under reflux for 4 h. The mixture was then cooled to ambient temperature, and the resulting solid product (I) was collected by filtration and then purified by column chromatography on silica gel using di­chloro­methane–ethanol (30:1 v/v) as eluant. Yellow crystals of compound (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in air, of a solution in ethanol–di­methyl­sulfoxide (1:1 v/v) [yield 30%, m.p. 559 K (with decomposition)]. MS (EI, 70 eV) m/z (%): 411 (54) (M+), 410 (98), 397 (31), 396 (100). Analysis found: C 72.9, H 5.2, N 10.2, S 7.7%; C25H21N3OS requires C 73.0, H 5.1, N 10.2, S 7.8%.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were located in difference maps and then treated as riding atoms. H atoms bonded to C atoms were permitted to ride in geometrically idealized positions, with C—H distances of 0.95 (aromatic and alkenic), 0.98 (CH3) or 0.99 Å (CH2) and with Uiso(H) = kUeq(C) where k = 1.5 for the methyl group, which was permitted to rotate but not to tilt, and 1.2 for all other H atoms bonded to C atoms. The H atom bonded to atom N3 was permitted to ride at the position located in a difference map, with Uiso(H) = 1.2Ueq(N), giving the N—H distance shown in Table 3. Five low-angle reflections, 110, 101, 011, 111 and 002, which had been wholly or partially attenuated by the beam-stop, were omitted from the final refinements.

Results and discussion top

The title compound, (I), and the 5,6,7,8,9,10-hexa­hydro derivative, (II), both crystallize in the space group P1 with Z' = 1; the unit-cell vectors for (I) and (II) are reasonably similar, but give slightly different unit-cell volumes as expected from the different molecular compositions (Hofmann, 2002). The compounds are not isostructural since, as noted below, the hydrogen-bonded assembly of the molecules in (I) and (II) is completely different; in addition, the molecules of compound (I) are only conformationally chiral, whereas those of compound (II) are configurationally chiral.

For the fused carbocyclic ring, the ring-puckering parameters (Cremer & Pople, 1975) calculated for the atom sequence C5A—C6—C7—C8—C9—C9A are Q = 0.500 (2) Å, θ = 52.6 (2)° and ϕ = 132.5 (3)°, corresponding closely to an envelope conformation where the ring is folded across the line C6···C8: the idealized values of the ring-puckering angles for this conformation are θ = 54.7° and ϕ = (60k)°, where k represents an integer (Boeyens, 1978). The reminder of the molecular conformation can be specified in terms of just three torsional angles (Table 2) defining the orientation of the peripheral substituents with respect to the adjacent ring system. For comparison, the corresponding torsional angles in the R enanti­omer of compound (II) are, respectively, 1.6 (2), -84.5 (3) and -23.7 (4)°, indicating a fairly close conformational similarity between (I) and (II). The dihedral angles between the pyridine ring in compound (I) and the two aryl rings (C51—56) and (C91–C96) are 74.14 (9) and 54.97 (9)°, respectively. The molecules of compound (I) thus exhibit no inter­nal symmetry and they are thus, as noted above, conformationally chiral, although the centrosymmetric space group confirms that equal numbers of the two conformational enanti­omers are present. Within the pyridine ring of compound (I), the bond lengths (Table 2) indicate typical heteroaromatic delocalization. The remaining bond distances in (I) show no unusual values: in particular there is no metrical evidence for the type of electronic polarization observed in the molecule of compound (II) (Becerra et al., 2010).

The molecules of compound (I) are linked by an inversion-related pair of almost linear N—H···O hydrogen bonds (Table 3) to form a cyclic centrosymmetric dimer (Fig. 2) characterized by an R22(8) (Bernstein et al., 1995) motif. The only short direction-specific contact between adjacent dimers is a C—H···π(arene) inter­action involving one of the C—H bonds of the methyl group (Table 3). This contact is not to be regarded as structurally significant, firstly because the methyl group is likely to be undergoing very rapid rotation about the C21—S21 bond (Riddell & Rogerson, 1996, 1997), and secondly because the H···(ring centroid) distance is long while the C—H···(ring centroid) angle is only 138° (cf. Wood et al., 2009). Hence, the supra­molecular assembly in (I) can be regarded as finite or zero-dimensional. By contrast, the supra­molecular assembly in (II) is two-dimensional, taking the form of bilayers comprising inversion-related pairs of sheets, built from a combination of two C—H···O hydrogen bonds and two C—H···π(arene) hydrogen bonds. Within the bilayer, each component sheet contains just one enanti­omeric form as the molecules comprising the sheet are all related by simple translations (Becerra et al., 2010).

Related literature top

For related literature, see: Alqasoumi et al. (2010); Becerra et al. (2010); Bernstein et al. (1995); Boeyens (1978); Cremer & Pople (1975); El-Gazzar, El-Enany & Mahmoud (2008); Hofmann (2002); Insuasty et al. (2008, 2013a, 2013b); Joshi & Viswanathan (2006); Riddell & Rogerson (1996, 1997); Selvi et al. (2006); Wood et al. (2009).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded R22(8) dimer. For the sale of clarity, H atoms bonded to C atoms have all been omitted. Atoms marked with an asterisk (*) are at the symmetry position (-x+2, -y+1, -z+1).
(9E)-9-Benzylidene-2-methylsulfanyl-5-phenyl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-4(3H)-one top
Crystal data top
C25H21N3OSZ = 2
Mr = 411.52F(000) = 432
Triclinic, P1Dx = 1.343 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2168 (16) ÅCell parameters from 4669 reflections
b = 9.7617 (18) Åθ = 3.7–27.5°
c = 12.6839 (17) ŵ = 0.18 mm1
α = 77.688 (16)°T = 120 K
β = 75.951 (11)°Block, yellow
γ = 68.117 (13)°0.34 × 0.30 × 0.28 mm
V = 1017.7 (3) Å3
Data collection top
Bruker–Nonius KappaCCD
diffractometer
4669 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode3311 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.7°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1212
Tmin = 0.821, Tmax = 0.950l = 1616
28315 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0342P)2 + 0.6598P]
where P = (Fo2 + 2Fc2)/3
4669 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C25H21N3OSγ = 68.117 (13)°
Mr = 411.52V = 1017.7 (3) Å3
Triclinic, P1Z = 2
a = 9.2168 (16) ÅMo Kα radiation
b = 9.7617 (18) ŵ = 0.18 mm1
c = 12.6839 (17) ÅT = 120 K
α = 77.688 (16)°0.34 × 0.30 × 0.28 mm
β = 75.951 (11)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
4669 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
3311 reflections with I > 2σ(I)
Tmin = 0.821, Tmax = 0.950Rint = 0.065
28315 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.06Δρmax = 0.34 e Å3
4669 reflectionsΔρmin = 0.31 e Å3
272 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.69387 (18)0.28333 (17)0.47393 (13)0.0200 (3)
C20.8019 (2)0.2844 (2)0.52232 (15)0.0203 (4)
N30.86286 (19)0.39788 (18)0.50421 (13)0.0229 (4)
H30.94240.38960.53480.027*
C40.8170 (2)0.5234 (2)0.42981 (15)0.0214 (4)
O40.88394 (17)0.61698 (16)0.41202 (12)0.0297 (3)
C4A0.6921 (2)0.5301 (2)0.37473 (15)0.0184 (4)
C50.6308 (2)0.6503 (2)0.29529 (15)0.0185 (4)
C5A0.5252 (2)0.6393 (2)0.23719 (15)0.0182 (4)
C60.4605 (2)0.7611 (2)0.14729 (16)0.0223 (4)
H6A0.54480.80170.10590.027*
H6B0.37150.84310.18080.027*
C70.4021 (2)0.7043 (2)0.06845 (16)0.0244 (4)
H7A0.49340.63290.02660.029*
H7B0.35060.78870.01560.029*
C80.2833 (2)0.6276 (2)0.13201 (17)0.0244 (4)
H8A0.19150.69950.17310.029*
H8B0.24360.59380.07990.029*
C90.3602 (2)0.4955 (2)0.21102 (15)0.0202 (4)
C9A0.4776 (2)0.5115 (2)0.26666 (15)0.0180 (4)
N100.53123 (18)0.40011 (17)0.34554 (13)0.0192 (3)
C10A0.6393 (2)0.4068 (2)0.39696 (15)0.0188 (4)
S210.88995 (6)0.13658 (6)0.61849 (4)0.02601 (14)
C210.8091 (2)0.0012 (2)0.60934 (18)0.0283 (5)
H21A0.81170.00410.53210.042*
H21B0.69890.02450.64880.042*
H21C0.87250.09920.64210.042*
C510.6735 (2)0.7885 (2)0.27651 (15)0.0187 (4)
C520.6090 (2)0.8855 (2)0.35568 (16)0.0224 (4)
H520.53920.86310.42010.027*
C530.6460 (2)1.0142 (2)0.34097 (16)0.0246 (4)
H530.60021.08040.39460.030*
C540.7500 (2)1.0467 (2)0.24794 (17)0.0260 (4)
H540.77611.13460.23790.031*
C550.8155 (2)0.9498 (2)0.16989 (17)0.0263 (4)
H550.88750.97120.10650.032*
C560.7769 (2)0.8219 (2)0.18364 (16)0.0226 (4)
H560.82140.75690.12920.027*
C970.3365 (2)0.3642 (2)0.22874 (15)0.0216 (4)
H970.39650.28720.27690.026*
C910.2268 (2)0.3271 (2)0.18121 (15)0.0211 (4)
C920.0693 (2)0.4207 (2)0.17904 (17)0.0259 (4)
H920.03090.51270.20750.031*
C930.0314 (2)0.3800 (2)0.13561 (17)0.0276 (5)
H930.13790.44460.13450.033*
C940.0228 (2)0.2458 (2)0.09391 (16)0.0268 (5)
H940.04570.21900.06340.032*
C950.1780 (3)0.1511 (2)0.09714 (16)0.0261 (4)
H950.21530.05850.06960.031*
C960.2789 (2)0.1908 (2)0.14029 (16)0.0230 (4)
H960.38470.12490.14220.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0203 (8)0.0213 (8)0.0190 (8)0.0078 (7)0.0047 (7)0.0011 (6)
C20.0186 (9)0.0204 (10)0.0183 (9)0.0038 (8)0.0021 (8)0.0017 (7)
N30.0217 (8)0.0253 (9)0.0253 (9)0.0097 (7)0.0111 (7)0.0003 (7)
C40.0199 (9)0.0222 (10)0.0218 (10)0.0064 (8)0.0045 (8)0.0031 (8)
O40.0293 (8)0.0269 (8)0.0402 (9)0.0149 (6)0.0180 (7)0.0039 (6)
C4A0.0161 (9)0.0208 (10)0.0178 (9)0.0055 (7)0.0008 (7)0.0057 (7)
C50.0168 (9)0.0199 (9)0.0185 (9)0.0060 (7)0.0005 (7)0.0051 (7)
C5A0.0163 (9)0.0176 (9)0.0191 (9)0.0038 (7)0.0016 (7)0.0046 (7)
C60.0248 (10)0.0197 (10)0.0236 (10)0.0076 (8)0.0084 (8)0.0011 (8)
C70.0312 (11)0.0220 (10)0.0225 (10)0.0093 (8)0.0121 (9)0.0007 (8)
C80.0262 (10)0.0212 (10)0.0295 (11)0.0082 (8)0.0127 (9)0.0023 (8)
C90.0185 (9)0.0205 (10)0.0214 (10)0.0054 (8)0.0037 (8)0.0044 (8)
C9A0.0173 (9)0.0177 (9)0.0180 (9)0.0048 (7)0.0027 (7)0.0033 (7)
N100.0192 (8)0.0185 (8)0.0208 (8)0.0061 (6)0.0047 (6)0.0038 (6)
C10A0.0165 (9)0.0198 (10)0.0182 (9)0.0046 (7)0.0015 (7)0.0034 (7)
S210.0242 (3)0.0277 (3)0.0246 (3)0.0076 (2)0.0097 (2)0.0037 (2)
C210.0273 (11)0.0243 (11)0.0294 (11)0.0070 (9)0.0068 (9)0.0031 (9)
C510.0180 (9)0.0176 (9)0.0212 (9)0.0052 (7)0.0086 (8)0.0001 (7)
C520.0203 (9)0.0244 (10)0.0223 (10)0.0060 (8)0.0053 (8)0.0038 (8)
C530.0263 (10)0.0229 (10)0.0257 (11)0.0059 (8)0.0074 (8)0.0071 (8)
C540.0305 (11)0.0191 (10)0.0327 (11)0.0113 (8)0.0109 (9)0.0009 (8)
C550.0279 (11)0.0265 (11)0.0250 (10)0.0126 (9)0.0015 (8)0.0019 (8)
C560.0225 (10)0.0232 (10)0.0217 (10)0.0069 (8)0.0026 (8)0.0052 (8)
C970.0226 (10)0.0214 (10)0.0209 (10)0.0069 (8)0.0064 (8)0.0013 (8)
C910.0249 (10)0.0222 (10)0.0188 (9)0.0114 (8)0.0046 (8)0.0007 (8)
C920.0257 (10)0.0279 (11)0.0259 (10)0.0097 (9)0.0036 (8)0.0074 (9)
C930.0207 (10)0.0345 (12)0.0298 (11)0.0096 (9)0.0046 (8)0.0081 (9)
C940.0313 (11)0.0331 (12)0.0232 (10)0.0189 (9)0.0074 (9)0.0012 (9)
C950.0367 (12)0.0213 (10)0.0242 (10)0.0121 (9)0.0093 (9)0.0029 (8)
C960.0266 (10)0.0207 (10)0.0220 (10)0.0090 (8)0.0070 (8)0.0010 (8)
Geometric parameters (Å, º) top
N1—C21.294 (2)C21—H21A0.9800
N1—C10A1.394 (2)C21—H21B0.9800
C2—N31.374 (2)C21—H21C0.9800
C2—S211.7567 (19)C51—C561.387 (3)
N3—C41.373 (2)C51—C521.399 (3)
N3—H30.8801C52—C531.385 (3)
C4—O41.237 (2)C52—H520.9500
C4—C4A1.461 (3)C53—C541.389 (3)
N10—C10A1.343 (2)C53—H530.9500
C10A—C4A1.410 (3)C54—C551.387 (3)
C4A—C51.411 (3)C54—H540.9500
C5—C5A1.400 (3)C55—C561.388 (3)
C5—C511.498 (3)C55—H550.9500
C5A—C9A1.422 (3)C56—H560.9500
C5A—C61.514 (3)C97—C911.476 (3)
C6—C71.522 (3)C97—H970.9500
C6—H6A0.9900C91—C921.401 (3)
C6—H6B0.9900C91—C961.402 (3)
C7—C81.527 (3)C92—C931.392 (3)
C7—H7A0.9900C92—H920.9500
C7—H7B0.9900C93—C941.387 (3)
C8—C91.511 (3)C93—H930.9500
C8—H8A0.9900C94—C951.389 (3)
C8—H8B0.9900C94—H940.9500
C9—C971.342 (3)C95—C961.386 (3)
C9—C9A1.495 (3)C95—H950.9500
C9A—N101.343 (2)C96—H960.9500
S21—C211.799 (2)
C2—N1—C10A116.22 (16)C2—S21—C21101.51 (9)
N1—C2—N3124.83 (17)S21—C21—H21A109.5
N1—C2—S21123.03 (15)S21—C21—H21B109.5
N3—C2—S21112.13 (13)H21A—C21—H21B109.5
C4—N3—C2123.11 (16)S21—C21—H21C109.5
C4—N3—H3115.3H21A—C21—H21C109.5
C2—N3—H3121.2H21B—C21—H21C109.5
O4—C4—N3119.98 (17)C56—C51—C52119.05 (17)
O4—C4—C4A125.54 (17)C56—C51—C5121.94 (17)
N3—C4—C4A114.44 (16)C52—C51—C5119.00 (17)
C10A—C4A—C5119.23 (16)C53—C52—C51120.51 (18)
C10A—C4A—C4118.26 (16)C53—C52—H52119.7
C5—C4A—C4122.36 (17)C51—C52—H52119.7
C5A—C5—C4A118.46 (17)C52—C53—C54120.12 (19)
C5A—C5—C51120.91 (16)C52—C53—H53119.9
C4A—C5—C51120.59 (16)C54—C53—H53119.9
C5—C5A—C9A117.98 (16)C55—C54—C53119.47 (18)
C5—C5A—C6121.32 (16)C55—C54—H54120.3
C9A—C5A—C6120.69 (16)C53—C54—H54120.3
C5A—C6—C7111.98 (16)C54—C55—C56120.54 (19)
C5A—C6—H6A109.2C54—C55—H55119.7
C7—C6—H6A109.2C56—C55—H55119.7
C5A—C6—H6B109.2C51—C56—C55120.29 (19)
C7—C6—H6B109.2C51—C56—H56119.9
H6A—C6—H6B107.9C55—C56—H56119.9
C6—C7—C8110.10 (16)C9—C97—C91126.78 (17)
C6—C7—H7A109.6C9—C97—H97116.6
C8—C7—H7A109.6C91—C97—H97116.6
C6—C7—H7B109.6C92—C91—C96118.20 (17)
C8—C7—H7B109.6C92—C91—C97122.42 (18)
H7A—C7—H7B108.2C96—C91—C97119.33 (17)
C9—C8—C7110.73 (16)C93—C92—C91120.64 (19)
C9—C8—H8A109.5C93—C92—H92119.7
C7—C8—H8A109.5C91—C92—H92119.7
C9—C8—H8B109.5C94—C93—C92120.41 (19)
C7—C8—H8B109.5C94—C93—H93119.8
H8A—C8—H8B108.1C92—C93—H93119.8
C97—C9—C9A118.93 (17)C93—C94—C95119.46 (18)
C97—C9—C8124.17 (17)C93—C94—H94120.3
C9A—C9—C8116.78 (16)C95—C94—H94120.3
N10—C9A—C5A123.25 (16)C96—C95—C94120.43 (19)
N10—C9A—C9115.97 (16)C96—C95—H95119.8
C5A—C9A—C9120.77 (16)C94—C95—H95119.8
C9A—N10—C10A118.69 (16)C95—C96—C91120.84 (18)
N10—C10A—N1114.79 (16)C95—C96—H96119.6
N10—C10A—C4A122.22 (17)C91—C96—H96119.6
N1—C10A—C4A122.99 (16)
C10A—N1—C2—N31.0 (3)C9A—N10—C10A—N1177.11 (16)
C10A—N1—C2—S21177.95 (14)C9A—N10—C10A—C4A3.3 (3)
N1—C2—N3—C41.3 (3)C2—N1—C10A—N10177.87 (17)
S21—C2—N3—C4177.72 (15)C2—N1—C10A—C4A2.5 (3)
C2—N3—C4—O4175.20 (18)C5—C4A—C10A—N100.5 (3)
C2—N3—C4—C4A2.8 (3)C4—C4A—C10A—N10176.30 (17)
O4—C4—C4A—C10A173.84 (19)C5—C4A—C10A—N1179.87 (17)
N3—C4—C4A—C10A4.0 (3)C4—C4A—C10A—N14.1 (3)
O4—C4—C4A—C51.8 (3)N1—C2—S21—C217.03 (19)
N3—C4—C4A—C5179.62 (17)N3—C2—S21—C21172.05 (14)
C10A—C4A—C5—C5A3.2 (3)C5A—C5—C51—C5675.2 (2)
C4—C4A—C5—C5A172.40 (17)C4A—C5—C51—C56106.9 (2)
C10A—C4A—C5—C51174.73 (17)C5A—C5—C51—C52105.7 (2)
C4—C4A—C5—C519.7 (3)C4A—C5—C51—C5272.2 (2)
C4A—C5—C5A—C9A4.0 (3)C56—C51—C52—C530.8 (3)
C51—C5—C5A—C9A173.86 (17)C5—C51—C52—C53179.97 (17)
C4A—C5—C5A—C6177.27 (17)C51—C52—C53—C541.1 (3)
C51—C5—C5A—C64.8 (3)C52—C53—C54—C550.4 (3)
C5—C5A—C6—C7158.42 (18)C53—C54—C55—C560.6 (3)
C9A—C5A—C6—C722.9 (3)C52—C51—C56—C550.1 (3)
C5A—C6—C7—C853.5 (2)C5—C51—C56—C55179.02 (17)
C6—C7—C8—C960.9 (2)C54—C55—C56—C510.8 (3)
C7—C8—C9—C97139.0 (2)C9A—C9—C97—C91179.76 (18)
C7—C8—C9—C9A37.0 (2)C8—C9—C97—C913.9 (3)
C5—C5A—C9A—N101.4 (3)C9—C97—C91—C9246.8 (3)
C6—C5A—C9A—N10179.91 (17)C9—C97—C91—C96135.7 (2)
C5—C5A—C9A—C9177.57 (17)C96—C91—C92—C931.1 (3)
C6—C5A—C9A—C91.1 (3)C97—C91—C92—C93178.58 (18)
C97—C9—C9A—N1011.1 (3)C91—C92—C93—C940.1 (3)
C8—C9—C9A—N10172.76 (17)C92—C93—C94—C950.9 (3)
C97—C9—C9A—C5A169.91 (18)C93—C94—C95—C960.9 (3)
C8—C9—C9A—C5A6.3 (3)C94—C95—C96—C910.1 (3)
C5A—C9A—N10—C10A2.3 (3)C92—C91—C96—C951.1 (3)
C9—C9A—N10—C10A178.69 (16)C97—C91—C96—C95178.68 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O4i0.881.862.735 (3)175
C21—H21C···Cg1ii0.982.993.777 (2)138
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC25H21N3OS
Mr411.52
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)9.2168 (16), 9.7617 (18), 12.6839 (17)
α, β, γ (°)77.688 (16), 75.951 (11), 68.117 (13)
V3)1017.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.34 × 0.30 × 0.28
Data collection
DiffractometerBruker–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.821, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections
28315, 4669, 3311
Rint0.065
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.107, 1.06
No. of reflections4669
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.31

Computer programs: COLLECT (Hooft, 1998), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top
N10—C10A1.343 (2)C5—C5A1.400 (3)
C10A—C4A1.410 (3)C5A—C9A1.422 (3)
C4A—C51.411 (3)C9A—N101.343 (2)
N1—C2—S21—C217.03 (19)C9—C97—C91—C9246.8 (3)
C4A—C5—C51—C5272.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O4i0.881.862.735 (3)175
C21—H21C···Cg1ii0.982.993.777 (2)138
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z+1.
 

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