7-Benzyl-3-(4-fluoro-phen-yl)-2-propyl-amino-5,6,7,8-tetra-hydro-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one.

In the title compound, C(25)H(25)FN(4)OS, the thienopyrimidine fused-ring system is close to planar (r.m.s. deviation = 0.0089 Å), with a maximum deviation of 0.0261 (17) Å for the N atom adjacent to the benzene ring. This thienopyrimidine fused-ring system forms dihedral angles of 64.73 (3) and 81.56 (5)° with the adjacent benzyl and fluoro-phenyl rings, respectively. Inter-molecular N-H⋯F and C-H⋯F hydrogen bonding, as well as C-F⋯π inter-actions [F⋯centroid = 3.449 (3) Å; C-F⋯centroid = 91.87 (15)°], 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 ▶); Mavrova et al. (2010 ▶). For similar crystal structures, see: Xie et al. (2008) ▶; Chen et al. (2011 ▶).

Experimental

Crystal data

C25H25FN4OS

M = 448.55

Orthorhombic,

a = 17.921 (7) Å

b = 18.427 (7) Å

c = 27.114 (10) Å

V = 8954 (6) Å3

Z = 16

Mo Kα radiation

μ = 0.18 mm−1

T = 296 K

0.26 × 0.25 × 0.23 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.955, T max = 0.960

46089 measured reflections

5152 independent reflections

4234 reflections with I > 2σ(I)

R int = 0.107

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.194

S = 1.05

5152 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.30 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010318/gw2115sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010318/gw2115Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010318/gw2115Isup3.cml

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

C25H25FN4OS	F(000) = 3776
Mr = 448.55	Dx = 1.331 Mg m−3
Orthorhombic, Ibca	Melting point: 432 K
Hall symbol: -I 2b 2c	Mo Kα radiation, λ = 0.71073 Å
a = 17.921 (7) Å	θ = 2.2–27.5°
b = 18.427 (7) Å	µ = 0.18 mm−1
c = 27.114 (10) Å	T = 296 K
V = 8954 (6) Å3	Block, white
Z = 16	0.26 × 0.25 × 0.23 mm

Bruker SMART CCD diffractometer	5152 independent reflections
Radiation source: fine-focus sealed tube	4234 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.107
CCD Profile fitting scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.955, Tmax = 0.960	k = −23→23
46089 measured reflections	l = −35→35

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.090P)2 + 9.9439P] where P = (Fo2 + 2Fc2)/3
5152 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.87109 (4)	0.17415 (4)	0.30237 (2)	0.0591 (2)
C1	0.46974 (17)	0.04644 (18)	0.32327 (13)	0.0698 (8)
H1	0.4418	0.0066	0.3132	0.084*
C2	0.50154 (17)	0.09137 (18)	0.28892 (11)	0.0674 (8)
H2	0.4948	0.0820	0.2555	0.081*
C3	0.54325 (15)	0.15022 (16)	0.30340 (10)	0.0571 (6)
H3	0.5640	0.1805	0.2796	0.068*
C4	0.55497 (13)	0.16516 (14)	0.35321 (9)	0.0496 (6)
C5	0.52218 (15)	0.11933 (16)	0.38753 (10)	0.0587 (7)
H5	0.5290	0.1282	0.4210	0.070*
C6	0.47947 (17)	0.06071 (18)	0.37275 (12)	0.0673 (8)
H6	0.4573	0.0309	0.3962	0.081*
C7	0.60106 (14)	0.22989 (15)	0.36911 (11)	0.0583 (7)
H7A	0.5969	0.2669	0.3438	0.070*
H7B	0.5792	0.2495	0.3990	0.070*
C8	0.72121 (13)	0.19589 (15)	0.33405 (10)	0.0530 (6)
H8A	0.7181	0.2345	0.3098	0.064*
H8B	0.6990	0.1526	0.3200	0.064*
C9	0.80136 (13)	0.18162 (14)	0.34679 (9)	0.0495 (6)
C10	0.82718 (13)	0.17246 (13)	0.39342 (9)	0.0452 (5)
C11	0.77549 (13)	0.17373 (15)	0.43661 (9)	0.0522 (6)
H11A	0.7811	0.2191	0.4543	0.063*
H11B	0.7877	0.1343	0.4589	0.063*
C12	0.69484 (14)	0.16574 (15)	0.41885 (9)	0.0520 (6)
H12A	0.6863	0.1165	0.4076	0.062*
H12B	0.6608	0.1756	0.4458	0.062*
C13	0.90652 (12)	0.16038 (12)	0.39418 (9)	0.0452 (5)
C14	0.93774 (13)	0.15967 (14)	0.34782 (9)	0.0492 (6)
C15	1.05433 (13)	0.13502 (14)	0.37363 (9)	0.0513 (6)
C16	0.95394 (12)	0.14756 (13)	0.43557 (9)	0.0445 (5)
C17	1.07929 (12)	0.11374 (13)	0.46200 (9)	0.0444 (5)
C18	1.11037 (14)	0.16664 (13)	0.49144 (10)	0.0507 (6)
H18	1.0994	0.2153	0.4859	0.061*
C19	1.15808 (14)	0.14701 (16)	0.52937 (10)	0.0574 (6)
H19	1.1794	0.1819	0.5498	0.069*
C20	1.17280 (15)	0.07522 (17)	0.53586 (10)	0.0605 (7)
C21	1.14149 (17)	0.02195 (16)	0.50825 (13)	0.0688 (8)
H21	1.1518	−0.0266	0.5147	0.083*
C22	1.09393 (16)	0.04143 (14)	0.47039 (12)	0.0615 (7)
H22	1.0720	0.0060	0.4507	0.074*
C23	1.15905 (18)	0.1213 (2)	0.31582 (13)	0.0810 (10)
H23A	1.1625	0.1710	0.3043	0.097*
H23B	1.1256	0.0955	0.2938	0.097*
C24	1.2338 (2)	0.0875 (2)	0.31314 (14)	0.0900 (11)
H24A	1.2548	0.0963	0.2807	0.108*
H24B	1.2662	0.1104	0.3372	0.108*
C25	1.2322 (3)	0.0086 (2)	0.32243 (17)	0.1213 (17)
H25A	1.2107	−0.0005	0.3542	0.182*
H25B	1.2822	−0.0102	0.3216	0.182*
H25C	1.2028	−0.0149	0.2975	0.182*
N1	0.68111 (11)	0.21671 (11)	0.37846 (8)	0.0519 (5)
N2	1.01070 (11)	0.14831 (13)	0.33586 (8)	0.0560 (5)
N3	1.02934 (10)	0.13358 (11)	0.42237 (7)	0.0471 (5)
N4	1.12699 (12)	0.12111 (16)	0.36574 (9)	0.0667 (7)
H4A	1.1554	0.1119	0.3905	0.080*
O1	0.93579 (10)	0.14699 (11)	0.47917 (6)	0.0568 (5)
F1	1.22046 (12)	0.05586 (13)	0.57255 (7)	0.0979 (7)

	U11	U22	U33	U12	U13	U23
S1	0.0455 (4)	0.0870 (5)	0.0447 (4)	0.0112 (3)	−0.0047 (3)	0.0065 (3)
C1	0.0575 (16)	0.0736 (19)	0.078 (2)	−0.0005 (14)	−0.0060 (15)	−0.0112 (16)
C2	0.0616 (16)	0.090 (2)	0.0500 (15)	0.0039 (16)	−0.0082 (13)	−0.0146 (14)
C3	0.0490 (13)	0.0763 (17)	0.0460 (13)	0.0092 (12)	−0.0013 (11)	0.0003 (12)
C4	0.0362 (11)	0.0627 (14)	0.0499 (13)	0.0181 (10)	−0.0067 (10)	−0.0054 (11)
C5	0.0524 (14)	0.0802 (18)	0.0435 (13)	0.0193 (13)	−0.0041 (11)	−0.0007 (12)
C6	0.0564 (16)	0.0786 (19)	0.0668 (18)	0.0092 (14)	0.0029 (14)	0.0103 (15)
C7	0.0418 (12)	0.0654 (16)	0.0677 (17)	0.0201 (12)	−0.0108 (12)	−0.0123 (13)
C8	0.0432 (12)	0.0642 (15)	0.0516 (14)	0.0114 (11)	−0.0092 (11)	0.0023 (11)
C9	0.0403 (12)	0.0592 (14)	0.0489 (13)	0.0082 (10)	−0.0050 (10)	0.0013 (11)
C10	0.0392 (11)	0.0506 (12)	0.0457 (12)	0.0101 (9)	−0.0050 (9)	−0.0048 (10)
C11	0.0420 (12)	0.0700 (16)	0.0447 (13)	0.0140 (11)	−0.0056 (10)	−0.0060 (11)
C12	0.0425 (12)	0.0669 (15)	0.0465 (13)	0.0120 (11)	−0.0024 (10)	−0.0080 (11)
C13	0.0380 (11)	0.0518 (12)	0.0457 (12)	0.0073 (9)	−0.0039 (9)	−0.0040 (10)
C14	0.0401 (11)	0.0596 (14)	0.0478 (13)	0.0083 (10)	−0.0062 (10)	0.0014 (11)
C15	0.0398 (12)	0.0647 (15)	0.0493 (13)	0.0093 (11)	0.0002 (10)	−0.0035 (11)
C16	0.0363 (11)	0.0488 (12)	0.0484 (13)	0.0071 (9)	−0.0037 (9)	−0.0081 (10)
C17	0.0348 (10)	0.0525 (13)	0.0458 (12)	0.0037 (9)	−0.0066 (9)	−0.0040 (10)
C18	0.0453 (12)	0.0495 (13)	0.0572 (15)	0.0005 (10)	−0.0047 (11)	−0.0053 (11)
C19	0.0449 (13)	0.0731 (17)	0.0542 (15)	−0.0050 (12)	−0.0077 (11)	−0.0152 (13)
C20	0.0452 (13)	0.088 (2)	0.0485 (14)	0.0082 (13)	−0.0105 (11)	0.0052 (13)
C21	0.0661 (17)	0.0546 (15)	0.086 (2)	0.0117 (13)	−0.0186 (16)	0.0080 (15)
C22	0.0564 (15)	0.0500 (14)	0.0780 (19)	0.0051 (12)	−0.0196 (14)	−0.0104 (13)
C23	0.0612 (18)	0.112 (3)	0.070 (2)	0.0229 (18)	0.0134 (16)	0.0164 (19)
C24	0.083 (2)	0.121 (3)	0.066 (2)	0.025 (2)	0.0101 (18)	0.0016 (19)
C25	0.179 (5)	0.092 (3)	0.094 (3)	0.036 (3)	−0.002 (3)	−0.014 (2)
N1	0.0415 (10)	0.0570 (12)	0.0572 (12)	0.0142 (9)	−0.0088 (9)	−0.0070 (9)
N2	0.0419 (10)	0.0796 (15)	0.0465 (11)	0.0110 (10)	−0.0011 (9)	0.0005 (10)
N3	0.0370 (9)	0.0595 (12)	0.0448 (10)	0.0102 (8)	−0.0067 (8)	−0.0066 (9)
N4	0.0412 (11)	0.1052 (19)	0.0538 (13)	0.0170 (12)	−0.0007 (9)	0.0013 (13)
O1	0.0460 (9)	0.0815 (13)	0.0428 (9)	0.0111 (9)	−0.0057 (7)	−0.0078 (8)
F1	0.0855 (13)	0.1396 (19)	0.0686 (12)	0.0214 (13)	−0.0338 (10)	0.0128 (11)

S1—C14	1.737 (2)	C13—C16	1.427 (3)
S1—C9	1.741 (3)	C14—N2	1.363 (3)
C1—C2	1.370 (5)	C15—N2	1.312 (3)
C1—C6	1.378 (5)	C15—N4	1.344 (3)
C1—H1	0.9300	C15—N3	1.395 (3)
C2—C3	1.374 (4)	C16—O1	1.226 (3)
C2—H2	0.9300	C16—N3	1.421 (3)
C3—C4	1.394 (4)	C17—C18	1.377 (3)
C3—H3	0.9300	C17—C22	1.377 (3)
C4—C5	1.387 (4)	C17—N3	1.446 (3)
C4—C7	1.513 (4)	C18—C19	1.385 (4)
C5—C6	1.383 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.360 (4)
C6—H6	0.9300	C19—H19	0.9300
C7—N1	1.477 (3)	C20—F1	1.359 (3)
C7—H7A	0.9700	C20—C21	1.356 (4)
C7—H7B	0.9700	C21—C22	1.382 (4)
C8—N1	1.454 (3)	C21—H21	0.9300
C8—C9	1.501 (3)	C22—H22	0.9300
C8—H8A	0.9700	C23—N4	1.471 (4)
C8—H8B	0.9700	C23—C24	1.479 (5)
C9—C10	1.357 (3)	C23—H23A	0.9700
C10—C13	1.439 (3)	C23—H23B	0.9700
C10—C11	1.493 (3)	C24—C25	1.476 (6)
C11—C12	1.531 (3)	C24—H24A	0.9700
C11—H11A	0.9700	C24—H24B	0.9700
C11—H11B	0.9700	C25—H25A	0.9600
C12—N1	1.464 (3)	C25—H25B	0.9600
C12—H12A	0.9700	C25—H25C	0.9600
C12—H12B	0.9700	N4—H4A	0.8600
C13—C14	1.376 (3)
C14—S1—C9	90.85 (12)	C13—C14—S1	111.54 (18)
C2—C1—C6	119.6 (3)	N2—C15—N4	119.3 (2)
C2—C1—H1	120.2	N2—C15—N3	123.5 (2)
C6—C1—H1	120.2	N4—C15—N3	117.3 (2)
C3—C2—C1	120.6 (3)	O1—C16—N3	119.6 (2)
C3—C2—H2	119.7	O1—C16—C13	127.0 (2)
C1—C2—H2	119.7	N3—C16—C13	113.5 (2)
C2—C3—C4	121.0 (3)	C18—C17—C22	120.8 (2)
C2—C3—H3	119.5	C18—C17—N3	120.1 (2)
C4—C3—H3	119.5	C22—C17—N3	119.0 (2)
C5—C4—C3	117.8 (3)	C17—C18—C19	119.7 (2)
C5—C4—C7	121.3 (2)	C17—C18—H18	120.2
C3—C4—C7	120.9 (3)	C19—C18—H18	120.2
C6—C5—C4	121.0 (3)	C20—C19—C18	118.0 (2)
C6—C5—H5	119.5	C20—C19—H19	121.0
C4—C5—H5	119.5	C18—C19—H19	121.0
C1—C6—C5	120.1 (3)	F1—C20—C21	118.3 (3)
C1—C6—H6	120.0	F1—C20—C19	118.2 (3)
C5—C6—H6	120.0	C21—C20—C19	123.5 (2)
N1—C7—C4	116.7 (2)	C20—C21—C22	118.5 (3)
N1—C7—H7A	108.1	C20—C21—H21	120.7
C4—C7—H7A	108.1	C22—C21—H21	120.7
N1—C7—H7B	108.1	C21—C22—C17	119.5 (2)
C4—C7—H7B	108.1	C21—C22—H22	120.3
H7A—C7—H7B	107.3	C17—C22—H22	120.3
N1—C8—C9	109.2 (2)	N4—C23—C24	113.5 (3)
N1—C8—H8A	109.8	N4—C23—H23A	108.9
C9—C8—H8A	109.8	C24—C23—H23A	108.9
N1—C8—H8B	109.8	N4—C23—H23B	108.9
C9—C8—H8B	109.8	C24—C23—H23B	108.9
H8A—C8—H8B	108.3	H23A—C23—H23B	107.7
C10—C9—C8	124.2 (2)	C25—C24—C23	112.9 (4)
C10—C9—S1	112.95 (18)	C25—C24—H24A	109.0
C8—C9—S1	122.80 (18)	C23—C24—H24A	109.0
C9—C10—C13	111.7 (2)	C25—C24—H24B	109.0
C9—C10—C11	121.1 (2)	C23—C24—H24B	109.0
C13—C10—C11	127.2 (2)	H24A—C24—H24B	107.8
C10—C11—C12	109.7 (2)	C24—C25—H25A	109.5
C10—C11—H11A	109.7	C24—C25—H25B	109.5
C12—C11—H11A	109.7	H25A—C25—H25B	109.5
C10—C11—H11B	109.7	C24—C25—H25C	109.5
C12—C11—H11B	109.7	H25A—C25—H25C	109.5
H11A—C11—H11B	108.2	H25B—C25—H25C	109.5
N1—C12—C11	109.4 (2)	C8—N1—C12	111.55 (19)
N1—C12—H12A	109.8	C8—N1—C7	112.4 (2)
C11—C12—H12A	109.8	C12—N1—C7	113.4 (2)
N1—C12—H12B	109.8	C15—N2—C14	114.5 (2)
C11—C12—H12B	109.8	C15—N3—C16	122.68 (19)
H12A—C12—H12B	108.2	C15—N3—C17	120.66 (19)
C14—C13—C16	118.3 (2)	C16—N3—C17	116.58 (19)
C14—C13—C10	113.0 (2)	C15—N4—C23	121.6 (2)
C16—C13—C10	128.7 (2)	C15—N4—H4A	119.2
N2—C14—C13	127.5 (2)	C23—N4—H4A	119.2
N2—C14—S1	120.96 (19)
C6—C1—C2—C3	0.3 (5)	N3—C17—C18—C19	179.9 (2)
C1—C2—C3—C4	0.8 (4)	C17—C18—C19—C20	0.4 (4)
C2—C3—C4—C5	−1.0 (4)	C18—C19—C20—F1	179.0 (2)
C2—C3—C4—C7	179.9 (2)	C18—C19—C20—C21	−2.2 (5)
C3—C4—C5—C6	0.2 (4)	F1—C20—C21—C22	−179.0 (3)
C7—C4—C5—C6	179.3 (2)	C19—C20—C21—C22	2.2 (5)
C2—C1—C6—C5	−1.1 (4)	C20—C21—C22—C17	−0.5 (5)
C4—C5—C6—C1	0.9 (4)	C18—C17—C22—C21	−1.2 (4)
C5—C4—C7—N1	87.2 (3)	N3—C17—C22—C21	−179.9 (3)
C3—C4—C7—N1	−93.7 (3)	N4—C23—C24—C25	67.6 (5)
N1—C8—C9—C10	14.6 (4)	C9—C8—N1—C12	−49.8 (3)
N1—C8—C9—S1	−166.08 (19)	C9—C8—N1—C7	−178.5 (2)
C14—S1—C9—C10	−0.9 (2)	C11—C12—N1—C8	69.8 (3)
C14—S1—C9—C8	179.7 (2)	C11—C12—N1—C7	−162.1 (2)
C8—C9—C10—C13	−179.4 (2)	C4—C7—N1—C8	65.3 (3)
S1—C9—C10—C13	1.3 (3)	C4—C7—N1—C12	−62.4 (3)
C8—C9—C10—C11	2.0 (4)	N4—C15—N2—C14	178.2 (3)
S1—C9—C10—C11	−177.38 (19)	N3—C15—N2—C14	−1.0 (4)
C9—C10—C11—C12	15.1 (3)	C13—C14—N2—C15	1.7 (4)
C13—C10—C11—C12	−163.3 (2)	S1—C14—N2—C15	−177.2 (2)
C10—C11—C12—N1	−48.8 (3)	N2—C15—N3—C16	−0.9 (4)
C9—C10—C13—C14	−1.0 (3)	N4—C15—N3—C16	179.8 (2)
C11—C10—C13—C14	177.5 (2)	N2—C15—N3—C17	175.8 (2)
C9—C10—C13—C16	−179.1 (2)	N4—C15—N3—C17	−3.5 (4)
C11—C10—C13—C16	−0.5 (4)	O1—C16—N3—C15	−178.5 (2)
C16—C13—C14—N2	−0.4 (4)	C13—C16—N3—C15	2.2 (3)
C10—C13—C14—N2	−178.7 (2)	O1—C16—N3—C17	4.7 (3)
C16—C13—C14—S1	178.59 (18)	C13—C16—N3—C17	−174.7 (2)
C10—C13—C14—S1	0.3 (3)	C18—C17—N3—C15	101.6 (3)
C9—S1—C14—N2	179.4 (2)	C22—C17—N3—C15	−79.7 (3)
C9—S1—C14—C13	0.3 (2)	C18—C17—N3—C16	−81.5 (3)
C14—C13—C16—O1	179.2 (2)	C22—C17—N3—C16	97.2 (3)
C10—C13—C16—O1	−2.8 (4)	N2—C15—N4—C23	0.8 (5)
C14—C13—C16—N3	−1.5 (3)	N3—C15—N4—C23	−180.0 (3)
C10—C13—C16—N3	176.5 (2)	C24—C23—N4—C15	−165.6 (3)
C22—C17—C18—C19	1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24B···F1i	0.97	2.66	3.258 (5)	121
C25—H25A···F1i	0.96	2.56	3.096 (5)	116
N4—H4A···F1i	0.86	2.65	3.423 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24B⋯F1i	0.97	2.66	3.258 (5)	121
C25—H25A⋯F1i	0.96	2.56	3.096 (5)	116
N4—H4A⋯F1i	0.86	2.65	3.423 (3)	151

Symmetry code: (i) .