9-Furfuryl­idene-2,3-dimethyl-6,7,8,9-tetrahydro-4H-­thieno[2′,3′:4,5]pyrimidino[1,2-a]pyridin-4-one

Bozorov, K.A.; Elmuradov, B.Z.; Okmanov, R.Y.; Tashkhodjaev, B.; Shakhidoyatov, K.M.

doi:10.1107/S1600536810004101

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o552-o553

doi:10.1107/S1600536810004101

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9-Furfurylidene-2,3-dimethyl-6,7,8,9-tetrahydro-4H-thieno[2′,3′:4,5]pyrimidino[1,2-a]pyridin-4-one

Khurshed A. Bozorov,^a ^* Burkhon Zh. Elmuradov,^a Rasul Ya. Okmanov,^a Bakhodir Tashkhodjaev ^a and Khusnutdin M. Shakhidoyatov ^a

^aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: khurshed-m@mail.ru

(Received 27 January 2010; accepted 2 February 2010; online 6 February 2010)

The title compound, C₁₇H₁₆N₂O₂S, was obtained by condensation of 2,3-dimethylthieno[2′,3′:4,5]pyrimidino[1,2-a]pyridin-4-one with furfural in the presence of sodium hydroxide. One of the methylene groups of the tetrahydropyrido ring is disordered over two positions in a 0.87 (1):0.13 (1) ratio. The thieno[2,3-d]pyrimidin-4-one unit and the furan ring are both planar (r.m.s. deviation = 0.535 Å), and coplanar with each other, forming a dihedral angle of 5.4 (1)°. Four weak intermolecular hydrogen bonds (C—H⋯O and C—H⋯N) are observed in the structure, which join molecules into a network parallel to (101).

Related literature

For the synthesis of thieno[2,3-d]pyrimidin-4-ones and their derivatives, see: Melik-Ogandzhanyan et al. (1985 ); Csukonyi et al. (1986 ); Shvedov et al. (1975 ); Shakhidoyatov (1983 ); Gevald et al. (1966 ); Kapustina et al. (1992 ); Peet et al. (1986 ); Shodiyev et al. (1993 ); Bozorov et al. (2009 ). For the physiological activity of thieno[2,3-d]pyrimidin-4-ones and their derivatives, see: Kapustina et al. (1992); Blaskiewich et al. (1975 ); Wähäla et al. (2005 ); Lilienkampf et al. (2007 ); Han et al. (2007 ); Moore et al. (2006 ). For weak hydrogen bonds in alkaloids, see: Rajnikant et al. (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₆N₂O₂S
M_r = 312.39
Monoclinic, P 2₁ /c
a = 16.569 (3) Å
b = 11.034 (2) Å
c = 8.2775 (17) Å
β = 93.12 (3)°
V = 1511.1 (5) Å³
Z = 4
Cu Kα radiation
μ = 1.98 mm⁻¹
T = 295 K
0.70 × 0.25 × 0.25 mm

Data collection

Stoe Stadi-4 four-circle diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.749, T_max = 0.994
2398 measured reflections
2252 independent reflections
1875 reflections with I > 2σ(I)
θ_max = 60.0°
3 standard reflections every 60 min intensity decay: 8.8%

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.126
S = 1.06
2252 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3′—H3′A⋯O1′ⁱ	0.93	2.58	3.442 (3)	154
C4′—H4′A⋯N1ⁱ	0.93	2.66	3.568 (3)	166
C5A—H5AA⋯O1ⁱⁱ	0.96	2.55	3.486 (4)	166
C6A—H6AA⋯O1ⁱⁱ	0.96	2.62	3.571 (4)	171
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: STADI4 (Stoe & Cie, 1997 ); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810004101/zl2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004101/zl2270Isup2.hkl

checkCIF report

Comment top

Among heterocyclic compounds the thieno[2,3-d]pyrimidin-4-ones (Melik-Ogandzhanyan et al., 1985; Csukonyi et al., 1986; Shvedov et al., 1975; Shakhidoyatov 1983; Gevald et al., 1966; Kapustina et al., 1992; Peet et al., 1986; Shodiyev et al., 1993) make up a large group of substances that have various physiological activities (Kapustina et al., 1992; Blaskiewich et al., 1975; Wähäla et al., 2005; Lilienkampf et al., 2007; Han et al., 2007; Moore et al., 2006).

Condensation of 2,3-dimethylthieno[2',3':4,5]pyrimidino[1,2-a]pyridin-4-one with aromatic and heterocyclic aldehydes leads to the formation of new 8-aryliden derivatives. With this purpose in mind the reaction of 2,3-dimethylthieno[2',3':4,5]pyrimidino[1,2-a]pyridin-4-one with furfural was carried by boiling of equimolar amounts of the initial reagents over 4 hours in ethanol in the presence of sodium hydroxide (Bozorov et al., 2009) (Figure 1).

The structure of the synthesized compound has been investigated by ¹H NMR and XRD analysis. Figure 2 shows an ortep style plot of the molecular structure of the title compound. One of the methylene groups of the tetrahydropyrido ring (C10, C10A) is disordered over two positions. Refinement of the structure yielded an occupancy ratio of the disordered atoms (i.e. two conformers) of 0.87 (1):0.13 (1).

The π-electronic system of the thiophene, furan and pyrimidinone rings participate in conjugation with the π electrons of the nitrogen atoms as can be seen from the appreciable change of the bond lengths of valence bonds C4═O1 (1.226 (3) Å), C2—C8 (1.479 (3) Å), C12—C2' (1.437 (3) Å) from their standard values (Allen et al., 1987) and from the coplanarity of the thieno[2,3-d]pyrimidin-4-one moiety with the furan ring.

In the crystal structure of the title compound weak intermolecular C—H···X hydrogen bonds (Table 1) are observed as it is often the case in alkaloids (Rajnikant et al., 2005). Of them C3'—H···O1' and C4'—H···N1 lead to the formation of infinite chains, C5A—H···O1 and C6A—H···O1 join these chains in a flat network (Figure 3. and Table 1) parallel to the (1 0 1) plane.

Related literature top

For the synthesis of thieno[2,3-d]pyrimidin-4-ones and their derivatives, see: Melik-Ogandzhanyan et al. (1985); Csukonyi et al. (1986); Shvedov et al. (1975); Shakhidoyatov (1983); Gevald et al. (1966); Kapustina et al. (1992); Peet et al. (1986); Shodiyev et al. (1993); Bozorov et al. (2009). For the physiological activity of thieno[2,3-d]pyrimidin-4-ones and their derivatives, see: Kapustina et al. (1992); Blaskiewich et al. (1975); Wähäla et al. (2005); Lilienkampf et al. (2007); Han et al. (2007); Moore et al. (2006). For weak hydrogen bonds in alkaloids, see: Rajnikant et al. (2005). For bond-length data, see: Allen et al. (1987). .

Experimental top

0.02 g sodium hydroxide (0.5 mmole) was dissolved in 5 ml ethanol, and 0.234 g (1 mmole) of 2,3-dimethylthieno[2',3':4,5]pyrimidino[1,2-a]pyridin-4-one and 0.106 g (0.092 ml, d═1.1598 g/ml, 1.1 mmole) furfural were added (Figure 1). The mixture was heated to reflux on a water bath for 4 hours. The solvent was distilled off and the residue was recrystallized from a mixture of solvents – benzene: cyclohexane – 5:1. 0.26 g (83.4 %) of the title compound were obtained in the reaction. m.p. 449–451 K.

Yellow crystals suitable for X-ray analysis were obtained from a mixture of benzene and hexane (2:1) at room temperature.

¹H NMR (400 MHz, CDCl₃): 7.83 (1H, t, J═2.22 Hz, H-12), 7.48 (1H, d, J═1.98 Hz, H-3'), 6.56 (1H, d, J═3.46 Hz, H-5'), 6.45 (1H, dd, J═1.98 Hz, J═3.46 Hz, H-4'), 4.07 (2H, t, J═5.93 Hz, CH₂-11), 2.97 (2H, td, J═2.22 Hz, J═6.68 Hz, CH₂-9), 2.42 (3H, d, J═0.75 Hz, CH₃-5), 2.32 (3H, d, J═0.75 Hz, CH₃-6), 1.94-1.99 (2H, m, CH₂-10).

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4 (Stoe & Cie, 1997); data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Reaction scheme.
	Fig. 2. An Ortep sty;e plot of the structure and the numbering of atoms in (I) (dashed atoms indicate equivalent positions of disordeed atoms).
	Fig. 3. Packing view of the title compound showing the H-bonding networks in the crystal. Minor moiety disordered atoms are omitted for clarity.

9-Furfurylidene-2,3-dimethyl-6,7,8,9-tetrahydro-4H-thieno[2',3':4,5]pyrimidino[1,2-a]pyridin-4-one top

Crystal data top

C₁₇H₁₆N₂O₂S	F(000) = 656
M_r = 312.39	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 448(3) K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 16.569 (3) Å	Cell parameters from 14 reflections
b = 11.034 (2) Å	θ = 10–20°
c = 8.2775 (17) Å	µ = 1.98 mm⁻¹
β = 93.12 (3)°	T = 295 K
V = 1511.1 (5) Å³	Prizmatic, yellow
Z = 4	0.70 × 0.25 × 0.25 mm

Data collection top

Stoe Stadi-4 four-circle diffractometer	1875 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 60.0°, θ_min = 2.7°
Scan width (ω) = 1.56 – 1.80, scan ratio 2θ:ω = 1.00 I(Net) and sigma(I) calculated according to Blessing (1987)	h = 0→18
Absorption correction: ψ scan (North et al., 1968)	k = −12→0
T_min = 0.749, T_max = 0.994	l = −9→9
2398 measured reflections	3 standard reflections every 60 min
2252 independent reflections	intensity decay: 8.8%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0607P)² + 0.8817P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.004
2252 reflections	Δρ_max = 0.21 e Å⁻³
212 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (6)

Crystal data top

C₁₇H₁₆N₂O₂S	V = 1511.1 (5) Å³
M_r = 312.39	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 16.569 (3) Å	µ = 1.98 mm⁻¹
b = 11.034 (2) Å	T = 295 K
c = 8.2775 (17) Å	0.70 × 0.25 × 0.25 mm
β = 93.12 (3)°

Data collection top

Stoe Stadi-4 four-circle diffractometer	1875 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.749, T_max = 0.994	θ_max = 60.0°
2398 measured reflections	3 standard reflections every 60 min
2252 independent reflections	intensity decay: 8.8%

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.06	Δρ_max = 0.21 e Å⁻³
2252 reflections	Δρ_min = −0.20 e Å⁻³
212 parameters

Special details top

Experimental. ψ Scan Reflections used µ * R = 0.00

H K L, θ, χ, I_min/I_max: 2 0 0, 21.5, 84.7, 0.699

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.90729 (13)	0.21420 (19)	−0.1624 (3)	0.0835 (8)
S7	0.77689 (4)	0.60019 (6)	−0.01745 (10)	0.0595 (3)
N1	0.71466 (12)	0.37806 (19)	0.0356 (3)	0.0467 (6)
C2	0.72119 (14)	0.2591 (2)	0.0249 (3)	0.0418 (6)
N3	0.78599 (12)	0.20424 (19)	−0.0432 (3)	0.0458 (5)
C4	0.85116 (15)	0.2697 (3)	−0.1063 (3)	0.0518 (7)
C4A	0.84293 (15)	0.3988 (2)	−0.0951 (3)	0.0449 (6)
C5	0.89660 (15)	0.4932 (2)	−0.1467 (3)	0.0487 (6)
C5A	0.97383 (17)	0.4694 (3)	−0.2303 (4)	0.0679 (9)
H5AA	0.9986	0.5451	−0.2562	0.102*
H5AB	0.9618	0.4245	−0.3280	0.102*
H5AC	1.0102	0.4235	−0.1599	0.102*
C6	0.86857 (16)	0.6048 (3)	−0.1123 (3)	0.0531 (7)
C6A	0.90635 (19)	0.7268 (3)	−0.1409 (4)	0.0709 (9)
H6AA	0.9540	0.7164	−0.2005	0.106*
H6AB	0.9207	0.7645	−0.0388	0.106*
H6AC	0.8684	0.7772	−0.2016	0.106*
C7A	0.77579 (14)	0.4433 (2)	−0.0239 (3)	0.0450 (6)
C8	0.65649 (15)	0.1844 (2)	0.0904 (3)	0.0421 (6)
C9	0.65812 (17)	0.0487 (2)	0.0699 (3)	0.0538 (7)
H9A	0.6036	0.0194	0.0455	0.065*	0.867 (11)
H9B	0.6782	0.0114	0.1703	0.065*	0.867 (11)
H9C	0.6373	0.0109	0.1648	0.065*	0.133 (11)
H9D	0.6229	0.0265	−0.0228	0.065*	0.133 (11)
C10	0.7120 (3)	0.0122 (3)	−0.0664 (6)	0.0553 (13)	0.867 (11)
H10A	0.7188	−0.0751	−0.0657	0.066*	0.867 (11)
H10B	0.6857	0.0348	−0.1696	0.066*	0.867 (11)
C10A	0.7417 (14)	0.0010 (18)	0.046 (5)	0.059 (9)	0.133 (11)
H10C	0.7690	−0.0087	0.1520	0.071*	0.133 (11)
H10D	0.7364	−0.0790	−0.0017	0.071*	0.133 (11)
C11	0.79243 (19)	0.0704 (3)	−0.0502 (4)	0.0619 (8)
H11A	0.8235	0.0477	−0.1414	0.074*	0.867 (11)
H11B	0.8211	0.0414	0.0476	0.074*	0.867 (11)
H11C	0.7820	0.0459	−0.1619	0.074*	0.133 (11)
H11D	0.8479	0.0487	−0.0200	0.074*	0.133 (11)
C12	0.59817 (14)	0.2425 (2)	0.1664 (3)	0.0462 (6)
H12A	0.6022	0.3265	0.1678	0.055*
O1'	0.48028 (12)	0.28051 (16)	0.3048 (3)	0.0661 (6)
C2'	0.53057 (15)	0.1931 (2)	0.2458 (3)	0.0453 (6)
C3'	0.50203 (17)	0.0833 (2)	0.2865 (3)	0.0532 (7)
H3'A	0.5247	0.0088	0.2625	0.064*
C4'	0.43150 (17)	0.1016 (3)	0.3722 (4)	0.0581 (8)
H4'A	0.3989	0.0421	0.4144	0.070*
C5'	0.42112 (18)	0.2205 (3)	0.3803 (4)	0.0677 (9)
H5'A	0.3790	0.2580	0.4309	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0666 (14)	0.0566 (13)	0.132 (2)	0.0106 (11)	0.0528 (14)	−0.0037 (13)
S7	0.0568 (5)	0.0387 (4)	0.0861 (6)	−0.0057 (3)	0.0330 (4)	−0.0040 (3)
N1	0.0458 (12)	0.0368 (12)	0.0594 (13)	−0.0038 (9)	0.0206 (10)	−0.0035 (9)
C2	0.0426 (13)	0.0371 (14)	0.0465 (13)	0.0011 (11)	0.0084 (11)	−0.0033 (11)
N3	0.0448 (12)	0.0374 (12)	0.0562 (13)	0.0023 (9)	0.0121 (10)	−0.0027 (9)
C4	0.0450 (15)	0.0491 (16)	0.0630 (16)	0.0050 (12)	0.0176 (13)	−0.0004 (13)
C4A	0.0391 (13)	0.0477 (15)	0.0489 (14)	0.0007 (11)	0.0107 (11)	−0.0012 (11)
C5	0.0412 (14)	0.0499 (16)	0.0563 (15)	−0.0021 (12)	0.0144 (12)	0.0009 (12)
C5A	0.0466 (16)	0.068 (2)	0.092 (2)	−0.0008 (15)	0.0275 (15)	0.0024 (17)
C6	0.0466 (15)	0.0526 (16)	0.0615 (16)	−0.0084 (13)	0.0175 (13)	0.0020 (13)
C6A	0.068 (2)	0.0541 (18)	0.094 (2)	−0.0126 (15)	0.0291 (17)	0.0071 (16)
C7A	0.0421 (13)	0.0398 (14)	0.0543 (15)	−0.0018 (11)	0.0129 (11)	−0.0014 (11)
C8	0.0442 (14)	0.0357 (13)	0.0467 (14)	−0.0040 (11)	0.0061 (11)	−0.0004 (10)
C9	0.0596 (17)	0.0386 (15)	0.0645 (17)	−0.0044 (13)	0.0155 (14)	−0.0031 (12)
C10	0.065 (2)	0.0360 (17)	0.066 (3)	0.0019 (16)	0.010 (2)	−0.0066 (16)
C10A	0.048 (13)	0.032 (11)	0.10 (2)	0.004 (9)	0.008 (13)	0.013 (12)
C11	0.0681 (19)	0.0365 (14)	0.083 (2)	0.0089 (14)	0.0169 (16)	−0.0035 (14)
C12	0.0472 (14)	0.0337 (13)	0.0587 (15)	−0.0056 (11)	0.0115 (12)	−0.0006 (11)
O1'	0.0624 (12)	0.0378 (10)	0.1018 (15)	−0.0008 (9)	0.0407 (11)	0.0043 (10)
C2'	0.0444 (14)	0.0357 (13)	0.0567 (15)	−0.0030 (11)	0.0110 (12)	−0.0011 (11)
C3'	0.0576 (16)	0.0346 (14)	0.0692 (18)	−0.0072 (12)	0.0196 (14)	−0.0015 (12)
C4'	0.0539 (16)	0.0467 (16)	0.0760 (19)	−0.0121 (13)	0.0236 (14)	0.0027 (13)
C5'	0.0569 (17)	0.0501 (18)	0.100 (2)	−0.0057 (14)	0.0384 (17)	0.0024 (16)

Geometric parameters (Å, º) top

O1—C4	1.226 (3)	C9—H9A	0.9700
S7—C7A	1.732 (3)	C9—H9B	0.9700
S7—C6	1.748 (3)	C9—H9C	0.9700
N1—C2	1.321 (3)	C9—H9D	0.9700
N1—C7A	1.357 (3)	C10—C11	1.478 (5)
C2—N3	1.379 (3)	C10—H10A	0.9700
C2—C8	1.479 (3)	C10—H10B	0.9700
N3—C4	1.422 (3)	C10A—C11	1.41 (2)
N3—C11	1.482 (3)	C10A—H10C	0.9700
C4—C4A	1.435 (4)	C10A—H10D	0.9700
C4A—C7A	1.377 (3)	C11—H11A	0.9700
C4A—C5	1.449 (3)	C11—H11B	0.9700
C5—C6	1.352 (4)	C11—H11C	0.9700
C5—C5A	1.510 (4)	C11—H11D	0.9700
C5A—H5AA	0.9600	C12—C2'	1.437 (3)
C5A—H5AB	0.9600	C12—H12A	0.9300
C5A—H5AC	0.9600	O1'—C5'	1.363 (3)
C6—C6A	1.509 (4)	O1'—C2'	1.381 (3)
C6A—H6AA	0.9600	C2'—C3'	1.349 (3)
C6A—H6AB	0.9600	C3'—C4'	1.414 (4)
C6A—H6AC	0.9600	C3'—H3'A	0.9300
C8—C12	1.344 (3)	C4'—C5'	1.325 (4)
C8—C9	1.506 (3)	C4'—H4'A	0.9300
C9—C10A	1.51 (2)	C5'—H5'A	0.9300
C9—C10	1.531 (4)

C7A—S7—C6	91.33 (12)	C8—C9—H9C	109.1
C2—N1—C7A	116.0 (2)	C10A—C9—H9D	109.1
N1—C2—N3	122.1 (2)	C8—C9—H9D	109.1
N1—C2—C8	117.8 (2)	H9C—C9—H9D	107.8
N3—C2—C8	120.1 (2)	C11—C10—C9	112.2 (3)
C2—N3—C4	123.4 (2)	C11—C10—H10A	109.2
C2—N3—C11	120.8 (2)	C9—C10—H10A	109.2
C4—N3—C11	115.7 (2)	C11—C10—H10B	109.2
O1—C4—N3	119.5 (3)	C9—C10—H10B	109.2
O1—C4—C4A	126.7 (2)	H10A—C10—H10B	107.9
N3—C4—C4A	113.8 (2)	C11—C10A—C9	117.6 (17)
C7A—C4A—C4	117.6 (2)	C11—C10A—H10C	107.9
C7A—C4A—C5	113.2 (2)	C9—C10A—H10C	107.9
C4—C4A—C5	129.2 (2)	C11—C10A—H10D	107.9
C6—C5—C4A	111.6 (2)	C9—C10A—H10D	107.9
C6—C5—C5A	124.3 (2)	H10C—C10A—H10D	107.2
C4A—C5—C5A	124.0 (2)	C10A—C11—N3	118.1 (9)
C5—C5A—H5AA	109.5	C10—C11—N3	111.7 (3)
C5—C5A—H5AB	109.5	C10A—C11—H11A	130.9
H5AA—C5A—H5AB	109.5	C10—C11—H11A	109.3
C5—C5A—H5AC	109.5	N3—C11—H11A	109.3
H5AA—C5A—H5AC	109.5	C10—C11—H11B	109.3
H5AB—C5A—H5AC	109.5	N3—C11—H11B	109.3
C5—C6—C6A	129.0 (2)	H11A—C11—H11B	107.9
C5—C6—S7	112.7 (2)	C10A—C11—H11C	107.8
C6A—C6—S7	118.3 (2)	N3—C11—H11C	107.8
C6—C6A—H6AA	109.5	H11B—C11—H11C	139.2
C6—C6A—H6AB	109.5	C10A—C11—H11D	107.8
H6AA—C6A—H6AB	109.5	C10—C11—H11D	138.9
C6—C6A—H6AC	109.5	N3—C11—H11D	107.8
H6AA—C6A—H6AC	109.5	H11C—C11—H11D	107.1
H6AB—C6A—H6AC	109.5	C8—C12—C2'	129.2 (2)
N1—C7A—C4A	127.0 (2)	C8—C12—H12A	115.4
N1—C7A—S7	121.74 (18)	C2'—C12—H12A	115.4
C4A—C7A—S7	111.21 (19)	C5'—O1'—C2'	106.6 (2)
C12—C8—C2	117.4 (2)	C3'—C2'—O1'	108.2 (2)
C12—C8—C9	123.0 (2)	C3'—C2'—C12	138.3 (2)
C2—C8—C9	119.6 (2)	O1'—C2'—C12	113.4 (2)
C10A—C9—C8	112.6 (8)	C2'—C3'—C4'	107.9 (2)
C8—C9—C10	111.1 (2)	C2'—C3'—H3'A	126.0
C10A—C9—H9A	135.2	C4'—C3'—H3'A	126.0
C8—C9—H9A	109.4	C5'—C4'—C3'	106.2 (2)
C10—C9—H9A	109.4	C5'—C4'—H4'A	126.9
C8—C9—H9B	109.4	C3'—C4'—H4'A	126.9
C10—C9—H9B	109.4	C4'—C5'—O1'	111.1 (2)
H9A—C9—H9B	108.0	C4'—C5'—H5'A	124.5
C10A—C9—H9C	109.1	O1'—C5'—H5'A	124.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3′—H3′A···O1′ⁱ	0.93	2.58	3.442 (3)	154
C4′—H4′A···N1ⁱ	0.93	2.66	3.568 (3)	166
C5A—H5AA···O1ⁱⁱ	0.96	2.55	3.486 (4)	166
C6A—H6AA···O1ⁱⁱ	0.96	2.62	3.571 (4)	171

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₂S
M_r	312.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	16.569 (3), 11.034 (2), 8.2775 (17)
β (°)	93.12 (3)
V (Å³)	1511.1 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.98
Crystal size (mm)	0.70 × 0.25 × 0.25

Data collection
Diffractometer	Stoe Stadi-4 four-circle diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.749, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	2398, 2252, 1875
R_int	0.000
θ_max (°)	60.0
(sin θ/λ)_max (Å⁻¹)	0.562

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.126, 1.06
No. of reflections	2252
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: STADI4 (Stoe & Cie, 1997), X-RED (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3'—H3'A···O1'ⁱ	0.93	2.581	3.442 (3)	154
C4'—H4'A···N1ⁱ	0.93	2.659	3.568 (3)	166
C5A—H5AA···O1ⁱⁱ	0.96	2.545	3.486 (4)	166
C6A—H6AA···O1ⁱⁱ	0.96	2.619	3.571 (4)	171

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z−1/2.

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F3–T047).

References

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Volume 66| Part 3| March 2010| Pages o552-o553

doi:10.1107/S1600536810004101

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

9-Furfuryl­­idene-2,3-di­methyl-6,7,8,9-tetra­hydro-4H-­thieno[2′,3′:4,5]pyrimidino[1,2-a]pyridin-4-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9-Furfurylidene-2,3-dimethyl-6,7,8,9-tetrahydro-4H-thieno[2′,3′:4,5]pyrimidino[1,2-a]pyridin-4-one