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

The title compound, C(17)H(16)N(2)O(2)S, was obtained by condensation of 2,3-dimethyl-thieno[2',3':4,5]pyrimidino[1,2-a]pyridin-4-one with furfural in the presence of sodium hydroxide. One of the methyl-ene groups of the tetra-hydro-pyrido 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 inter-molecular hydrogen bonds (C-H⋯O and C-H⋯N) are observed in the structure, which join mol-ecules 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 = 312.39

Monoclinic,

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)

θmax = 60.0°

3 standard reflections every 60 min intensity decay: 8.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.126

S = 1.06

2252 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H16N2O2S	F(000) = 656
Mr = 312.39	Dx = 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

Stoe Stadi-4 four-circle diffractometer	1875 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
graphite	θmax = 60.0°, θmin = 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
Tmin = 0.749, Tmax = 0.994	l = −9→9
2398 measured reflections	3 standard reflections every 60 min
2252 independent reflections	intensity decay: 8.8%

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(Fo2) + (0.0607P)2 + 0.8817P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.004
2252 reflections	Δρmax = 0.21 e Å−3
212 parameters	Δρmin = −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)

Experimental. ψ Scan Reflections used µ * R = 0.00 H K L, θ, χ, Imin/Imax: 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.

	x	y	z	Uiso*/Ueq	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*

	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)

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

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

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) ; (ii) .