7-Benzyl-3-(4-fluoro­phen­yl)-2-(pyrrol­idin-1-yl)-5,6,7,8-tetra­hydro­pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one

Chen, H.; Hu, H.-J.; Yan, K.; Dai, Q.-H.

doi:10.1107/S1600536811030625

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2228

doi:10.1107/S1600536811030625

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7-Benzyl-3-(4-fluorophenyl)-2-(pyrrolidin-1-yl)-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one

Hong Chen,^a ^* Hai-Jun Hu,^b Kai Yan ^b and Qiu-Hong Dai ^b

^aCollege of Chemistry and Life Science, China Three Gorges University, Yichang 443002, People's Republic of China, and ^bHubei Key Laboratory of Natural Products Research and Development, Yichang 443002, People's Republic of China
^*Correspondence e-mail: chenhong3736@sina.com

(Received 13 July 2011; accepted 29 July 2011; online 2 August 2011)

In the title compound, C₂₆H₂₅FN₄OS, the thienopyrimidine fused-ring system is close to planar (r.m.s. deviation = 0.066 Å), with a maximum deviation of 0.1243 (17) Å for the N atom adjacent to the carbonyl group. This ring system forms dihedral angles of 67.5 (1) and 88.9 (1) ° with the adjacent six-membered rings. Intermolecular C—H⋯O hydrogen bonding and C—H⋯π interactions help to stabilize the crystal structure.

Related literature

For the biological and pharmaceutical properties of compounds containing the fused thienopyrimidine system, see: Amr et al. (2010 ); Huang et al. (2009 ); Jennings et al. (2005 ); Kikuchi et al. (2006 ); Mavrova et al. (2010 ); Santagati et al. (2002 ). For related structures, see: Hu et al. (2007 ); Xie et al. (2008 ).

Experimental

Crystal data

C₂₆H₂₅FN₄OS
M_r = 460.56
Triclinic, $[P \overline 1]$
a = 8.132 (10) Å
b = 9.736 (11) Å
c = 15.540 (18) Å
α = 99.742 (16)°
β = 99.636 (11)°
γ = 105.551 (14)°
V = 1139 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 296 K
0.23 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.960, T_max = 0.974
12210 measured reflections
5233 independent reflections
4018 reflections with I > 2σ(I)
R_int = 0.154

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.180
S = 1.05
5233 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1-C11-C10-C13-C16 and N2-C15-N3-C14-C13-C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1ⁱ	0.97	2.50	3.461 (5)	171
C24—H24B⋯O1ⁱⁱ	0.97	2.44	3.316 (5)	151
C25—H25B⋯Cg1ⁱⁱⁱ	0.97	2.86	3.693 (5)	144
C26—H26B⋯Cg2ⁱⁱⁱ	0.97	2.80	3.717 (5)	158
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811030625/zq2114sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030625/zq2114Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811030625/zq2114Isup3.cml

checkCIF report

Comment top

Derivatives of heterocycles containing the thienopyrimidine system have proved to show significant antifungal, antibacterical, anticonvulsant and angiotensin antagonistic activities (Amr et al. 2010; Huang et al. 2009; Jennings et al. 2005; Kikuchi et al. 2006; Mavrova et al. 2010; Santagati et al. 2002). Recently, we have focused on the synthesis of fused heterocyclic systems containing thienopyrimidine via aza-Wittig reaction under mild conditions. Some X-ray crystal structures of fused pyrimidinone derivatives have been reported (Hu et al., 2007; Xie et al., 2008). The title compound has potential use as a precursor for obtaining bioactive molecules with fluorescence properties. Herein, we report its crystal structure (Fig. 1 and 2).

In the crystal structure of the title compound, C₂₆H₂₅FN₄OS, the thienopyrimidine fused ring system are essentially coplanar (rms deviation = 0.066 Å) with a maximum deviation of 0.1243 (17) Å for atom N3. This ring system forms dihedral angles of 67.5 (1) and 88.9 (1) ° with the adjacent 6-membered rings C17–C22 and C1-C6, respectively. Intermolecular C—H···O hydrogen bondings (C8—H8B···O1ⁱ and C24—H24B···O1ⁱⁱ with symmetry codes: (i) -x+2, -y, -z+1; (ii) x-1, y, z) and C—H···π interactions (C25—H25B···Cg1ⁱⁱⁱ and C26—H26···Cg2ⁱⁱⁱ with Cg1 and Cg2 centroids of the S1-C11-C10-C13-C16 and N2-C15-N3-C14-C13-C16 rings and symmetry code: (iii) 1-x, 1-y, 1-z) help to stabilize the crystal structure of the title compound (Table 1).

Related literature top

For the biological and pharmaceutical properties of compounds containing the fused thienopyrimidine system, see: Amr et al. (2010); Huang et al. (2009); Jennings et al. (2005); Kikuchi et al. (2006); Mavrova et al. (2010); Santagati et al. (2002). For related structures, see: Hu et al. (2007); Xie et al. (2008).

Experimental top

Fluoro-4-isocyanatobenzene (2 mmol) under nitrogen atmosphere was added to a solution of iminophosphorane (2 mmol) in anhydrous CH₂Cl₂ (10 ml) at room temperature (Fig. 3). When the reaction mixture was left unstirred for 12 h at 273–278k, iminophosphorane was consumed (TLC monitored). The solvent was removed under reduced pressure and ether/petroleum ether (volume ratio 1:2, 20 ml) was added to precipitate triphenylphosphine oxide. Removal of the solvent gave carbodiimide, which was used directly without further purification. Pyrrolidine (2 mmol) was added to the solution of carbodiimide in anhydrous dichloromethane (10 ml). After the reaction mixture was left unstirred for 5–6 h, the solvent was removed and anhydrous EtOH (10 ml) with several drops of EtONa (in EtOH) was added to the mixture. The mixture was stirred for another 6–8 h at room temperature. The solution was condensed and the residual was recrystallized from EtOH to give the expected title compound as white crystals.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with 50% probability displacement ellipsoids. H atoms are omitted for clarity.
	Fig. 2. Packing diagram of the title compound projected along the a axis direction. H atoms are omitted for clarity.
	Fig. 3. Reaction scheme.

7-Benzyl-3-(4-fluorophenyl)-2-(pyrrolidin-1-yl)-5,6,7,8- tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one top

Crystal data top

C₂₆H₂₅FN₄OS	Z = 2
M_r = 460.56	F(000) = 484
Triclinic, P1	D_x = 1.343 Mg m⁻³
Hall symbol: -P 1	Melting point: 485 K
a = 8.132 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.736 (11) Å	Cell parameters from 2106 reflections
c = 15.540 (18) Å	θ = 2.7–27.5°
α = 99.742 (16)°	µ = 0.18 mm⁻¹
β = 99.636 (11)°	T = 296 K
γ = 105.551 (14)°	Block, colourless
V = 1139 (2) Å³	0.23 × 0.20 × 0.15 mm

Data collection top

Bruker SMART CCD diffractometer	5233 independent reflections
Radiation source: fine-focus sealed tube	4018 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.154
CCD Profile fitting scans	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.960, T_max = 0.974	k = −12→12
12210 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0691P)²] where P = (F_o² + 2F_c²)/3
5233 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₆H₂₅FN₄OS	γ = 105.551 (14)°
M_r = 460.56	V = 1139 (2) Å³
Triclinic, P1	Z = 2
a = 8.132 (10) Å	Mo Kα radiation
b = 9.736 (11) Å	µ = 0.18 mm⁻¹
c = 15.540 (18) Å	T = 296 K
α = 99.742 (16)°	0.23 × 0.20 × 0.15 mm
β = 99.636 (11)°

Data collection top

Bruker SMART CCD diffractometer	5233 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4018 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.974	R_int = 0.154
12210 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.05	Δρ_max = 0.48 e Å⁻³
5233 reflections	Δρ_min = −0.38 e Å⁻³
298 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

	x	y	z	U_iso*/U_eq
S1	0.44564 (6)	0.17251 (6)	0.31146 (3)	0.04008 (18)
N2	0.3853 (2)	0.28656 (17)	0.47059 (11)	0.0354 (4)
O1	0.7783 (2)	0.16116 (16)	0.60615 (10)	0.0477 (4)
N3	0.57983 (19)	0.29116 (16)	0.60532 (10)	0.0318 (3)
N4	0.3472 (2)	0.39607 (17)	0.60525 (11)	0.0349 (4)
C13	0.6094 (2)	0.16139 (18)	0.46627 (13)	0.0322 (4)
C15	0.4366 (2)	0.32359 (19)	0.55846 (13)	0.0315 (4)
C17	0.6746 (2)	0.3752 (2)	0.69460 (12)	0.0335 (4)
C14	0.6647 (2)	0.19681 (19)	0.56157 (13)	0.0328 (4)
C16	0.4790 (2)	0.21316 (19)	0.42757 (13)	0.0332 (4)
N1	0.7929 (2)	−0.04640 (17)	0.25491 (12)	0.0401 (4)
C10	0.6883 (2)	0.09292 (18)	0.40137 (13)	0.0329 (4)
C23	0.3336 (3)	0.4011 (2)	0.69915 (14)	0.0403 (4)
H23A	0.4258	0.4826	0.7396	0.048*
H23B	0.3403	0.3110	0.7161	0.048*
C11	0.6146 (3)	0.0929 (2)	0.31656 (13)	0.0351 (4)
C22	0.7449 (3)	0.5255 (2)	0.70756 (14)	0.0393 (4)
H22	0.7291	0.5706	0.6600	0.047*
C26	0.2043 (2)	0.4368 (2)	0.55417 (15)	0.0402 (5)
H26A	0.1182	0.3514	0.5136	0.048*
H26B	0.2495	0.5072	0.5200	0.048*
C9	0.8400 (3)	0.0331 (2)	0.41996 (14)	0.0381 (4)
H9A	0.7991	−0.0636	0.4318	0.046*
H9B	0.9257	0.0961	0.4726	0.046*
C12	0.6811 (3)	0.0451 (2)	0.23597 (14)	0.0399 (5)
H12A	0.5828	−0.0095	0.1865	0.048*
H12B	0.7473	0.1305	0.2184	0.048*
C18	0.7011 (3)	0.3054 (2)	0.76407 (14)	0.0452 (5)
H18	0.6543	0.2044	0.7545	0.054*
C8	0.9246 (3)	0.0243 (2)	0.33961 (15)	0.0435 (5)
H8A	0.9891	0.1222	0.3367	0.052*
H8B	1.0071	−0.0308	0.3473	0.052*
F1	0.9572 (3)	0.6188 (2)	0.94182 (12)	0.1047 (7)
C4	0.7603 (3)	−0.1314 (3)	0.09123 (16)	0.0513 (6)
C21	0.8389 (3)	0.6084 (3)	0.79164 (17)	0.0530 (6)
H21	0.8838	0.7097	0.8019	0.064*
C19	0.7981 (3)	0.3875 (3)	0.84799 (16)	0.0596 (6)
H19	0.8183	0.3429	0.8954	0.072*
C24	0.1546 (3)	0.4208 (3)	0.70031 (16)	0.0516 (6)
H24A	0.1543	0.4772	0.7580	0.062*
H24B	0.0648	0.3269	0.6874	0.062*
C25	0.1256 (3)	0.5036 (2)	0.62624 (17)	0.0504 (5)
H25A	0.0018	0.4885	0.6040	0.061*
H25B	0.1850	0.6077	0.6478	0.061*
C7	0.8822 (3)	−0.0742 (3)	0.18182 (17)	0.0520 (6)
H7A	0.9434	−0.1444	0.1933	0.062*
H7B	0.9690	0.0161	0.1816	0.062*
C20	0.8637 (3)	0.5372 (3)	0.85920 (16)	0.0621 (7)
C3	0.6252 (4)	−0.2613 (3)	0.0722 (2)	0.0719 (8)
H3	0.6104	−0.3154	0.1158	0.086*
C5	0.7773 (4)	−0.0546 (3)	0.0246 (2)	0.0709 (8)
H5	0.8661	0.0339	0.0366	0.085*
C6	0.6658 (5)	−0.1054 (4)	−0.0599 (2)	0.0875 (10)
H6	0.6812	−0.0521	−0.1039	0.105*
C2	0.5115 (5)	−0.3116 (4)	−0.0117 (2)	0.0837 (9)
H2	0.4197	−0.3982	−0.0237	0.100*
C1	0.5346 (6)	−0.2330 (4)	−0.0777 (2)	0.0861 (10)
H1	0.4599	−0.2680	−0.1342	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0408 (3)	0.0565 (3)	0.0278 (3)	0.0268 (2)	0.0029 (2)	0.0076 (2)
N2	0.0305 (8)	0.0460 (9)	0.0319 (8)	0.0176 (7)	0.0042 (6)	0.0075 (7)
O1	0.0476 (9)	0.0631 (9)	0.0363 (8)	0.0338 (7)	−0.0036 (6)	0.0069 (7)
N3	0.0275 (7)	0.0394 (8)	0.0274 (8)	0.0124 (6)	0.0015 (6)	0.0056 (7)
N4	0.0297 (8)	0.0465 (8)	0.0312 (8)	0.0171 (7)	0.0059 (6)	0.0080 (7)
C13	0.0308 (9)	0.0346 (9)	0.0324 (10)	0.0131 (7)	0.0039 (7)	0.0082 (8)
C15	0.0261 (8)	0.0378 (9)	0.0307 (9)	0.0104 (7)	0.0040 (7)	0.0092 (8)
C17	0.0274 (8)	0.0467 (10)	0.0265 (9)	0.0141 (8)	0.0035 (7)	0.0062 (8)
C14	0.0301 (9)	0.0346 (9)	0.0326 (10)	0.0120 (7)	0.0015 (7)	0.0065 (8)
C16	0.0301 (9)	0.0403 (9)	0.0284 (9)	0.0140 (7)	0.0015 (7)	0.0058 (8)
N1	0.0432 (9)	0.0462 (9)	0.0363 (9)	0.0233 (8)	0.0103 (7)	0.0063 (8)
C10	0.0313 (9)	0.0341 (8)	0.0330 (10)	0.0128 (7)	0.0027 (7)	0.0065 (8)
C23	0.0353 (10)	0.0537 (11)	0.0334 (10)	0.0143 (9)	0.0110 (8)	0.0093 (9)
C11	0.0377 (10)	0.0399 (9)	0.0307 (10)	0.0183 (8)	0.0056 (8)	0.0076 (8)
C22	0.0326 (9)	0.0475 (10)	0.0375 (11)	0.0147 (8)	0.0062 (8)	0.0064 (9)
C26	0.0283 (9)	0.0514 (11)	0.0429 (12)	0.0166 (8)	0.0051 (8)	0.0119 (9)
C9	0.0352 (10)	0.0406 (9)	0.0371 (10)	0.0169 (8)	0.0003 (8)	0.0041 (8)
C12	0.0457 (11)	0.0466 (10)	0.0332 (10)	0.0233 (9)	0.0094 (9)	0.0090 (9)
C18	0.0461 (12)	0.0581 (12)	0.0318 (11)	0.0178 (10)	0.0051 (9)	0.0117 (10)
C8	0.0380 (11)	0.0500 (11)	0.0460 (12)	0.0208 (9)	0.0074 (9)	0.0097 (10)
F1	0.1166 (17)	0.1151 (14)	0.0450 (10)	0.0321 (12)	−0.0342 (10)	−0.0244 (10)
C4	0.0655 (15)	0.0610 (13)	0.0401 (12)	0.0356 (12)	0.0211 (11)	0.0099 (11)
C21	0.0433 (12)	0.0515 (12)	0.0502 (14)	0.0117 (10)	−0.0017 (10)	−0.0087 (11)
C19	0.0610 (15)	0.0860 (18)	0.0301 (11)	0.0277 (13)	−0.0020 (10)	0.0119 (12)
C24	0.0349 (11)	0.0754 (15)	0.0473 (13)	0.0192 (10)	0.0149 (9)	0.0119 (12)
C25	0.0361 (11)	0.0599 (13)	0.0606 (15)	0.0225 (10)	0.0135 (10)	0.0123 (12)
C7	0.0541 (13)	0.0638 (13)	0.0486 (14)	0.0317 (11)	0.0187 (11)	0.0111 (11)
C20	0.0575 (15)	0.0801 (17)	0.0335 (12)	0.0234 (13)	−0.0117 (10)	−0.0104 (12)
C3	0.102 (2)	0.0659 (16)	0.0445 (15)	0.0245 (16)	0.0109 (14)	0.0097 (13)
C5	0.0764 (19)	0.0890 (19)	0.0595 (18)	0.0321 (16)	0.0261 (15)	0.0278 (16)
C6	0.111 (3)	0.109 (3)	0.056 (2)	0.043 (2)	0.0215 (19)	0.037 (2)
C2	0.108 (3)	0.0735 (18)	0.0561 (19)	0.0235 (17)	0.0034 (16)	−0.0004 (16)
C1	0.121 (3)	0.100 (2)	0.0404 (15)	0.053 (2)	0.0078 (17)	0.0041 (16)

Geometric parameters (Å, º) top

S1—C16	1.739 (3)	C9—H9B	0.9700
S1—C11	1.747 (2)	C12—H12A	0.9700
N2—C15	1.316 (3)	C12—H12B	0.9700
N2—C16	1.357 (3)	C18—C19	1.388 (3)
O1—C14	1.222 (2)	C18—H18	0.9300
N3—C15	1.406 (2)	C8—H8A	0.9700
N3—C14	1.438 (3)	C8—H8B	0.9700
N3—C17	1.452 (3)	F1—C20	1.364 (3)
N4—C15	1.354 (3)	C4—C5	1.380 (4)
N4—C23	1.475 (3)	C4—C3	1.383 (4)
N4—C26	1.478 (3)	C4—C7	1.499 (4)
C13—C16	1.384 (3)	C21—C20	1.369 (4)
C13—C14	1.427 (3)	C21—H21	0.9300
C13—C10	1.446 (3)	C19—C20	1.380 (4)
C17—C22	1.387 (3)	C19—H19	0.9300
C17—C18	1.386 (3)	C24—C25	1.535 (3)
N1—C12	1.463 (3)	C24—H24A	0.9700
N1—C7	1.473 (3)	C24—H24B	0.9700
N1—C8	1.476 (3)	C25—H25A	0.9700
C10—C11	1.353 (3)	C25—H25B	0.9700
C10—C9	1.506 (3)	C7—H7A	0.9700
C23—C24	1.521 (3)	C7—H7B	0.9700
C23—H23A	0.9700	C3—C2	1.391 (4)
C23—H23B	0.9700	C3—H3	0.9300
C11—C12	1.497 (3)	C5—C6	1.390 (5)
C22—C21	1.386 (3)	C5—H5	0.9300
C22—H22	0.9300	C6—C1	1.354 (5)
C26—C25	1.518 (3)	C6—H6	0.9300
C26—H26A	0.9700	C2—C1	1.387 (5)
C26—H26B	0.9700	C2—H2	0.9300
C9—C8	1.524 (3)	C1—H1	0.9300
C9—H9A	0.9700

C16—S1—C11	91.27 (9)	C11—C12—H12B	109.5
C15—N2—C16	115.47 (16)	H12A—C12—H12B	108.1
C15—N3—C14	121.92 (17)	C19—C18—C17	119.4 (2)
C15—N3—C17	121.57 (16)	C19—C18—H18	120.3
C14—N3—C17	115.13 (15)	C17—C18—H18	120.3
C15—N4—C23	127.56 (16)	N1—C8—C9	111.67 (19)
C15—N4—C26	117.88 (18)	N1—C8—H8A	109.3
C23—N4—C26	111.67 (16)	C9—C8—H8A	109.3
C16—C13—C14	118.39 (17)	N1—C8—H8B	109.3
C16—C13—C10	112.99 (18)	C9—C8—H8B	109.3
C14—C13—C10	128.06 (17)	H8A—C8—H8B	107.9
N2—C15—N4	118.25 (17)	C5—C4—C3	117.9 (3)
N2—C15—N3	122.75 (17)	C5—C4—C7	120.9 (3)
N4—C15—N3	118.99 (18)	C3—C4—C7	121.2 (2)
C22—C17—C18	120.97 (19)	C20—C21—C22	118.2 (2)
C22—C17—N3	118.44 (17)	C20—C21—H21	120.9
C18—C17—N3	120.52 (18)	C22—C21—H21	120.9
O1—C14—C13	126.76 (18)	C20—C19—C18	118.2 (2)
O1—C14—N3	119.67 (19)	C20—C19—H19	120.9
C13—C14—N3	113.47 (15)	C18—C19—H19	120.9
N2—C16—C13	127.03 (19)	C23—C24—C25	103.86 (17)
N2—C16—S1	121.94 (14)	C23—C24—H24A	111.0
C13—C16—S1	111.04 (14)	C25—C24—H24A	111.0
C12—N1—C7	111.41 (18)	C23—C24—H24B	111.0
C12—N1—C8	110.24 (16)	C25—C24—H24B	111.0
C7—N1—C8	109.4 (2)	H24A—C24—H24B	109.0
C11—C10—C13	111.91 (18)	C26—C25—C24	103.37 (18)
C11—C10—C9	120.74 (18)	C26—C25—H25A	111.1
C13—C10—C9	127.28 (18)	C24—C25—H25A	111.1
N4—C23—C24	103.68 (16)	C26—C25—H25B	111.1
N4—C23—H23A	111.0	C24—C25—H25B	111.1
C24—C23—H23A	111.0	H25A—C25—H25B	109.1
N4—C23—H23B	111.0	N1—C7—C4	113.4 (2)
C24—C23—H23B	111.0	N1—C7—H7A	108.9
H23A—C23—H23B	109.0	C4—C7—H7A	108.9
C10—C11—C12	124.32 (19)	N1—C7—H7B	108.9
C10—C11—S1	112.73 (15)	C4—C7—H7B	108.9
C12—C11—S1	122.64 (15)	H7A—C7—H7B	107.7
C21—C22—C17	119.8 (2)	F1—C20—C21	118.2 (3)
C21—C22—H22	120.1	F1—C20—C19	118.5 (3)
C17—C22—H22	120.1	C21—C20—C19	123.3 (2)
N4—C26—C25	103.64 (19)	C4—C3—C2	120.4 (3)
N4—C26—H26A	111.0	C4—C3—H3	119.8
C25—C26—H26A	111.0	C2—C3—H3	119.8
N4—C26—H26B	111.0	C4—C5—C6	122.0 (3)
C25—C26—H26B	111.0	C4—C5—H5	119.0
H26A—C26—H26B	109.0	C6—C5—H5	119.0
C10—C9—C8	109.86 (18)	C1—C6—C5	119.5 (3)
C10—C9—H9A	109.7	C1—C6—H6	120.3
C8—C9—H9A	109.7	C5—C6—H6	120.3
C10—C9—H9B	109.7	C1—C2—C3	120.2 (4)
C8—C9—H9B	109.7	C1—C2—H2	119.9
H9A—C9—H9B	108.2	C3—C2—H2	119.9
N1—C12—C11	110.81 (17)	C6—C1—C2	120.1 (3)
N1—C12—H12A	109.5	C6—C1—H1	120.0
C11—C12—H12A	109.5	C2—C1—H1	120.0
N1—C12—H12B	109.5

C16—N2—C15—N4	−179.48 (15)	C9—C10—C11—S1	−178.14 (13)
C16—N2—C15—N3	0.6 (3)	C16—S1—C11—C10	1.92 (16)
C23—N4—C15—N2	155.38 (18)	C16—S1—C11—C12	−172.02 (17)
C26—N4—C15—N2	−3.6 (2)	C18—C17—C22—C21	−1.9 (3)
C23—N4—C15—N3	−24.7 (3)	N3—C17—C22—C21	−178.84 (18)
C26—N4—C15—N3	176.30 (15)	C15—N4—C26—C25	175.64 (16)
C14—N3—C15—N2	−9.2 (3)	C23—N4—C26—C25	13.4 (2)
C17—N3—C15—N2	156.74 (18)	C11—C10—C9—C8	18.0 (2)
C14—N3—C15—N4	170.88 (16)	C13—C10—C9—C8	−158.70 (18)
C17—N3—C15—N4	−23.2 (2)	C7—N1—C12—C11	−170.65 (17)
C15—N3—C17—C22	−55.7 (2)	C8—N1—C12—C11	−49.0 (2)
C14—N3—C17—C22	111.1 (2)	C10—C11—C12—N1	19.6 (3)
C15—N3—C17—C18	127.3 (2)	S1—C11—C12—N1	−167.21 (13)
C14—N3—C17—C18	−65.8 (2)	C22—C17—C18—C19	0.6 (3)
C16—C13—C14—O1	−179.38 (18)	N3—C17—C18—C19	177.5 (2)
C10—C13—C14—O1	−8.6 (3)	C12—N1—C8—C9	66.5 (2)
C16—C13—C14—N3	−3.1 (2)	C7—N1—C8—C9	−170.69 (17)
C10—C13—C14—N3	167.70 (16)	C10—C9—C8—N1	−48.3 (2)
C15—N3—C14—O1	−173.49 (17)	C17—C22—C21—C20	2.0 (3)
C17—N3—C14—O1	19.7 (2)	C17—C18—C19—C20	0.5 (4)
C15—N3—C14—C13	9.9 (2)	N4—C23—C24—C25	−29.0 (2)
C17—N3—C14—C13	−156.85 (16)	N4—C26—C25—C24	−31.0 (2)
C15—N2—C16—C13	6.9 (3)	C23—C24—C25—C26	37.6 (2)
C15—N2—C16—S1	−173.02 (14)	C12—N1—C7—C4	−51.8 (3)
C14—C13—C16—N2	−5.5 (3)	C8—N1—C7—C4	−173.91 (18)
C10—C13—C16—N2	−177.61 (17)	C5—C4—C7—N1	118.8 (3)
C14—C13—C16—S1	174.45 (14)	C3—C4—C7—N1	−60.0 (3)
C10—C13—C16—S1	2.31 (19)	C22—C21—C20—F1	179.6 (2)
C11—S1—C16—N2	177.55 (16)	C22—C21—C20—C19	−0.8 (4)
C11—S1—C16—C13	−2.38 (14)	C18—C19—C20—F1	179.2 (2)
C16—C13—C10—C11	−0.9 (2)	C18—C19—C20—C21	−0.4 (4)
C14—C13—C10—C11	−172.11 (18)	C5—C4—C3—C2	0.1 (4)
C16—C13—C10—C9	176.07 (17)	C7—C4—C3—C2	178.9 (3)
C14—C13—C10—C9	4.9 (3)	C3—C4—C5—C6	−1.2 (4)
C15—N4—C23—C24	−150.15 (19)	C7—C4—C5—C6	180.0 (3)
C26—N4—C23—C24	9.9 (2)	C4—C5—C6—C1	0.9 (5)
C13—C10—C11—C12	172.87 (17)	C4—C3—C2—C1	1.2 (5)
C9—C10—C11—C12	−4.3 (3)	C5—C6—C1—C2	0.4 (5)
C13—C10—C11—S1	−0.9 (2)	C3—C2—C1—C6	−1.4 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1-C11-C10-C13-C16 and N2-C15-N3-C14-C13-C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1ⁱ	0.97	2.50	3.461 (5)	171
C24—H24B···O1ⁱⁱ	0.97	2.44	3.316 (5)	151
C25—H25B···Cg1ⁱⁱⁱ	0.97	2.86	3.693 (5)	144
C26—H26B···Cg2ⁱⁱⁱ	0.97	2.80	3.717 (5)	158

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅FN₄OS
M_r	460.56
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.132 (10), 9.736 (11), 15.540 (18)
α, β, γ (°)	99.742 (16), 99.636 (11), 105.551 (14)
V (Å³)	1139 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.23 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	12210, 5233, 4018
R_int	0.154
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.180, 1.05
No. of reflections	5233
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.38

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1-C11-C10-C13-C16 and N2-C15-N3-C14-C13-C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1ⁱ	0.97	2.50	3.461 (5)	171
C24—H24B···O1ⁱⁱ	0.97	2.44	3.316 (5)	151
C25—H25B···Cg1ⁱⁱⁱ	0.97	2.86	3.693 (5)	144
C26—H26B···Cg2ⁱⁱⁱ	0.97	2.80	3.717 (5)	158

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

Acknowledgements

This work was supported financially by the Science Foundation of Hubei Province Education Department, China (project No. D20091301) and the Excellent Fund for Scientific Research and Special Projects in China Three Gorges University, China (project No. KJ2009B004).

References

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Volume 67| Part 9| September 2011| Page o2228

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

7-Benzyl-3-(4-fluoro­phen­yl)-2-(pyrrol­idin-1-yl)-5,6,7,8-tetra­hydro­pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

7-Benzyl-3-(4-fluorophenyl)-2-(pyrrolidin-1-yl)-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one