6-(4-Fluoro­pheneth­yl)-7-imino-3-phenyl-2,3,6,7-tetra­hydro-1,3-thia­zolo[4,5-d]pyrimidine-2-thione

Liang, Y.; He, H.-W.; Yang, Z.-W.

doi:10.1107/S1600536809047576

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3098

doi:10.1107/S1600536809047576

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6-(4-Fluorophenethyl)-7-imino-3-phenyl-2,3,6,7-tetrahydro-1,3-thiazolo[4,5-d]pyrimidine-2-thione

Ying Liang,^a,^b ^* Hong-Wu He ^b and Zi-Wen Yang ^a

^aHubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Science, Wuhan 430064, People's Republic of China, and ^bKey Laboratory of Pesticides & Chemical Biology of the Ministry of Education, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: ly.liang8@gmail.com

(Received 10 November 2009; accepted 10 November 2009; online 14 November 2009)

In the title compound, C₁₉H₁₅FN₄S₂, the mean plane of the thiazolopyrimidine makes a dihedral angle of 77.6 (1)° with the attached phenyl ring. The crystal packing is stabilized by intermolecular C—H⋯N hydrogen bonds and weak C—H—π stacking interactions.

Related literature

For the biological activity of thiazolo[4,5-d]pyrimidine derivatives, see: Balkan et al. (2002 ); Bekhit et al. (2003 ); Danel et al. (1998 ); Fahmy et al. (2003 ). For the synthesis of thiazolo [4,5-d]pyrimidines via tandem aza-Wittig and cyclization reactions of iminophosphorane and alkylamines, see: Liang et al. (2007 ). For C—H⋯π interactions, see: Janiak (2000 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₅FN₄S₂
M_r = 382.47
Monoclinic, P 2₁ /n
a = 8.6449 (13) Å
b = 12.3780 (19) Å
c = 16.546 (3) Å
β = 91.531 (3)°
V = 1769.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.910, T_max = 0.939
13207 measured reflections
4047 independent reflections
3442 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.119
S = 1.05
4047 reflections
238 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯N3ⁱ	0.93	2.61	3.486 (3)	156
C19—H19⋯Cg3ⁱⁱ	0.93	2.74	3.637 (2)	161
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z. Cg3 is the centroid of the C1–C6 ring.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047576/jh2113sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047576/jh2113Isup2.hkl

checkCIF report

Comment top

Thiazolo[4,5-d]pyrimidine derivatives, which can be considered as thia-analogues of the natural purine bases such as adenine and guanine, have acquired a growing importance as anticancer agents (Fahmy et al., 2003), antiviral agents used in the treatment of human cytomegalovirus (Bekhit et al., 2003), antitumour agents (Balkan et al.,2002) and antibacterial agents (Danel et al., 1998).

An important synthetic route of our previous reports for thiazolo [4,5-d]pyrimidines is the tandem aza-Wittig and cyclization reaction of iminophosphorane and alkylamines (Liang et al., 2007). Recently, we have developed a new cyclization process to synthesize novel thiazolo[4,5-d]pyrimidine derivatives. In this paper, we report the structure of the title compound, (I)(Fig. 1).

In the molecule, all bond lengths and angles are normal (Allen et al., 1987). The mean plane of the thiazolopyrimidine fragment makes dihedral angle of 77.58 (10)° with the attached phenyl ring fragment. In the crystal structure, intermolecular C—H···N hydrogen-bonding interactions stabilize the structure (Table 1). In addition, short intermolecular distances between the centroids of the C1···C6 ring, Cg3, and C19···H19A [C19—H19···Cg3ⁱ = 2.740 (3) Å; symmetry code: (i) 1 - x, 1 - y, -z] indicate the existence of C—H-π stacking interactions (Janiak, 2000), which stabilize the crystal packing (Fig. 2) together with hydrogen-bonding interactions.

Related literature top

For the biological activity of thiazolo[4,5-d]pyrimidine derivatives, see: Balkan et al. (2002); Bekhit et al. (2003); Danel et al. (1998); Fahmy et al. (2003). For the synthesis of thiazolo [4,5-d]pyrimidines via the tandem aza-Wittig and cyclization reaction of iminophosphorane and alkylamines, see: Liang et al. (2007). For C—H-π stacking interactions, see: Janiak (2000). For bond-length data, see: Allen et al. (1987). Cg3 is the centroid of the C1–C6 ring.

Experimental top

To a suspension of 5-cyano-4-ethoxymethyleneamino-3-phenyl-3H-thiazolin- 2-thione (0.87 g 5 mmol) in 15 mL dry acetonitrile was added all at once 0.5 g (3.6 mmol) 4-fluorophenylethylamine. After standing at room temperature for 1.5 h, then the solution concentrated under vacuum and the residue was recrystallized from dichloromethane to give the title compound (yield 72.8%). Colourless crystals of (I) suitable for X-ray structure analysis were grown from the mixture of dichloromethane and ethanol (v/v, 1:3).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Crystal Packing diagram of (I). Hydrogen bonds are shown as dashed lines.

6-(4-Fluorophenethyl)-7-imino-3-phenyl-2,3,6,7-tetrahydro-1,3-thiazolo[4,5-d]pyrimidine-2-thione top

Crystal data top

C₁₉H₁₅FN₄S₂	F(000) = 792
M_r = 382.47	D_x = 1.435 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.6449 (13) Å	Cell parameters from 5242 reflections
b = 12.3780 (19) Å	θ = 2.5–27.9°
c = 16.546 (3) Å	µ = 0.32 mm⁻¹
β = 91.531 (3)°	T = 298 K
V = 1769.9 (5) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4047 independent reflections
Radiation source: fine-focus sealed tube	3442 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
T_min = 0.910, T_max = 0.939	k = −15→16
13207 measured reflections	l = −20→21

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.063P)² + 0.3948P] where P = (F_o² + 2F_c²)/3
4047 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₉H₁₅FN₄S₂	V = 1769.9 (5) Å³
M_r = 382.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6449 (13) Å	µ = 0.32 mm⁻¹
b = 12.3780 (19) Å	T = 298 K
c = 16.546 (3) Å	0.30 × 0.20 × 0.20 mm
β = 91.531 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4047 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3442 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.939	R_int = 0.023
13207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.31 e Å⁻³
4047 reflections	Δρ_min = −0.24 e Å⁻³
238 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
C1	0.4958 (2)	1.34258 (14)	0.58804 (13)	0.0535 (5)
C2	0.4537 (2)	1.33892 (14)	0.50835 (13)	0.0542 (5)
H2	0.4863	1.3917	0.4726	0.065*
C3	0.3607 (2)	1.25414 (15)	0.48189 (11)	0.0502 (4)
H3	0.3306	1.2503	0.4276	0.060*
C4	0.31153 (19)	1.17484 (13)	0.53462 (11)	0.0429 (4)
C5	0.3617 (2)	1.18055 (15)	0.61453 (11)	0.0504 (4)
H5	0.3335	1.1265	0.6503	0.060*
C6	0.4530 (2)	1.26536 (16)	0.64208 (12)	0.0572 (5)
H6	0.4846	1.2697	0.6961	0.069*
C7	0.2083 (2)	1.08369 (14)	0.50454 (11)	0.0482 (4)
H7A	0.1203	1.1133	0.4745	0.058*
H7B	0.1696	1.0439	0.5503	0.058*
C8	0.29661 (19)	1.00780 (14)	0.45073 (12)	0.0467 (4)
H8A	0.3450	1.0496	0.4087	0.056*
H8B	0.3782	0.9732	0.4827	0.056*
C9	0.10871 (19)	0.95138 (14)	0.34270 (10)	0.0422 (4)
C10	0.03504 (19)	0.85689 (13)	0.30865 (10)	0.0411 (4)
C11	0.04789 (18)	0.75959 (13)	0.34560 (9)	0.0379 (3)
C12	0.1989 (2)	0.82329 (14)	0.44484 (11)	0.0458 (4)
H12	0.2567	0.8135	0.4925	0.055*
C13	−0.0990 (2)	0.70793 (14)	0.23294 (10)	0.0445 (4)
C14	−0.02508 (18)	0.56612 (13)	0.33171 (10)	0.0402 (4)
C15	0.0719 (3)	0.49373 (17)	0.29640 (13)	0.0621 (5)
H15	0.1341	0.5146	0.2541	0.075*
C16	0.0753 (3)	0.38912 (19)	0.32496 (16)	0.0780 (7)
H16	0.1398	0.3386	0.3014	0.094*
C17	−0.0147 (3)	0.35897 (17)	0.38718 (18)	0.0776 (8)
H17	−0.0116	0.2881	0.4058	0.093*
C18	−0.1101 (3)	0.4326 (2)	0.42259 (16)	0.0739 (7)
H18	−0.1711	0.4117	0.4653	0.089*
C19	−0.1156 (2)	0.53768 (16)	0.39494 (12)	0.0554 (5)
H19	−0.1796	0.5882	0.4188	0.066*
N1	0.19862 (15)	0.92398 (11)	0.41267 (8)	0.0411 (3)
N2	0.12708 (17)	0.73932 (11)	0.41615 (9)	0.0459 (3)
N3	0.1072 (2)	1.04959 (13)	0.31970 (11)	0.0605 (4)
H3A	0.052 (3)	1.0564 (19)	0.2764 (15)	0.073*
N4	−0.02702 (16)	0.67676 (11)	0.30352 (8)	0.0397 (3)
F1	0.58230 (17)	1.42773 (10)	0.61527 (9)	0.0823 (4)
S1	−0.07386 (6)	0.84673 (4)	0.21932 (3)	0.05356 (16)
S2	−0.19713 (7)	0.63041 (4)	0.16868 (3)	0.06299 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0557 (10)	0.0390 (9)	0.0653 (12)	−0.0015 (7)	−0.0051 (9)	−0.0124 (8)
C2	0.0649 (11)	0.0400 (9)	0.0579 (12)	−0.0030 (8)	0.0053 (9)	0.0022 (8)
C3	0.0616 (11)	0.0468 (10)	0.0418 (9)	0.0013 (8)	−0.0036 (8)	−0.0013 (7)
C4	0.0455 (9)	0.0374 (8)	0.0457 (9)	0.0022 (7)	0.0017 (7)	−0.0069 (7)
C5	0.0657 (11)	0.0424 (9)	0.0431 (10)	0.0013 (8)	0.0027 (8)	−0.0003 (7)
C6	0.0738 (13)	0.0516 (11)	0.0456 (10)	0.0017 (9)	−0.0113 (9)	−0.0088 (8)
C7	0.0463 (9)	0.0461 (9)	0.0523 (10)	−0.0049 (7)	0.0040 (8)	−0.0077 (8)
C8	0.0384 (8)	0.0437 (9)	0.0576 (11)	−0.0028 (7)	−0.0038 (7)	−0.0108 (8)
C9	0.0456 (9)	0.0420 (9)	0.0391 (8)	−0.0044 (7)	0.0005 (7)	0.0010 (7)
C10	0.0478 (9)	0.0415 (8)	0.0337 (8)	−0.0036 (7)	−0.0048 (7)	0.0028 (6)
C11	0.0403 (8)	0.0388 (8)	0.0344 (8)	−0.0022 (6)	−0.0019 (6)	−0.0006 (6)
C12	0.0493 (9)	0.0426 (9)	0.0448 (10)	0.0028 (7)	−0.0131 (7)	−0.0014 (7)
C13	0.0541 (10)	0.0429 (9)	0.0361 (8)	−0.0027 (7)	−0.0056 (7)	0.0005 (7)
C14	0.0455 (8)	0.0356 (8)	0.0390 (8)	−0.0024 (6)	−0.0096 (7)	−0.0015 (6)
C15	0.0763 (14)	0.0584 (12)	0.0516 (11)	0.0159 (10)	0.0021 (10)	−0.0024 (9)
C16	0.1057 (19)	0.0501 (12)	0.0772 (16)	0.0275 (12)	−0.0187 (14)	−0.0099 (11)
C17	0.0875 (16)	0.0422 (11)	0.101 (2)	−0.0070 (11)	−0.0404 (15)	0.0170 (11)
C18	0.0622 (12)	0.0699 (15)	0.0891 (17)	−0.0130 (11)	−0.0077 (11)	0.0346 (13)
C19	0.0493 (10)	0.0549 (11)	0.0621 (12)	0.0020 (8)	0.0031 (8)	0.0128 (9)
N1	0.0389 (7)	0.0388 (7)	0.0453 (8)	−0.0018 (5)	−0.0053 (6)	−0.0052 (6)
N2	0.0560 (8)	0.0401 (7)	0.0409 (8)	−0.0006 (6)	−0.0147 (6)	0.0024 (6)
N3	0.0840 (12)	0.0420 (8)	0.0547 (10)	−0.0113 (8)	−0.0114 (9)	0.0082 (7)
N4	0.0479 (7)	0.0373 (7)	0.0335 (7)	−0.0034 (5)	−0.0060 (5)	0.0010 (5)
F1	0.0964 (10)	0.0541 (7)	0.0954 (10)	−0.0209 (7)	−0.0147 (8)	−0.0206 (7)
S1	0.0767 (3)	0.0453 (3)	0.0377 (3)	−0.0082 (2)	−0.0170 (2)	0.00820 (18)
S2	0.0860 (4)	0.0531 (3)	0.0483 (3)	−0.0078 (2)	−0.0276 (3)	−0.0050 (2)

Geometric parameters (Å, º) top

C1—C2	1.359 (3)	C10—S1	1.7356 (16)
C1—F1	1.362 (2)	C11—N2	1.361 (2)
C1—C6	1.367 (3)	C11—N4	1.390 (2)
C2—C3	1.386 (3)	C12—N2	1.294 (2)
C2—H2	0.9300	C12—N1	1.355 (2)
C3—C4	1.387 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—N4	1.364 (2)
C4—C5	1.382 (2)	C13—S2	1.6501 (17)
C4—C7	1.515 (2)	C13—S1	1.7472 (18)
C5—C6	1.384 (3)	C14—C15	1.369 (3)
C5—H5	0.9300	C14—C19	1.369 (3)
C6—H6	0.9300	C14—N4	1.447 (2)
C7—C8	1.515 (2)	C15—C16	1.378 (3)
C7—H7A	0.9700	C15—H15	0.9300
C7—H7B	0.9700	C16—C17	1.359 (4)
C8—N1	1.470 (2)	C16—H16	0.9300
C8—H8A	0.9700	C17—C18	1.371 (4)
C8—H8B	0.9700	C17—H17	0.9300
C9—N3	1.274 (2)	C18—C19	1.379 (3)
C9—N1	1.418 (2)	C18—H18	0.9300
C9—C10	1.439 (2)	C19—H19	0.9300
C10—C11	1.354 (2)	N3—H3A	0.86 (2)

C2—C1—F1	118.50 (18)	C10—C11—N2	125.78 (15)
C2—C1—C6	122.77 (17)	C10—C11—N4	113.49 (14)
F1—C1—C6	118.72 (18)	N2—C11—N4	120.72 (14)
C1—C2—C3	118.01 (18)	N2—C12—N1	126.76 (15)
C1—C2—H2	121.0	N2—C12—H12	116.6
C3—C2—H2	121.0	N1—C12—H12	116.6
C2—C3—C4	121.47 (17)	N4—C13—S2	127.02 (13)
C2—C3—H3	119.3	N4—C13—S1	109.46 (12)
C4—C3—H3	119.3	S2—C13—S1	123.52 (10)
C5—C4—C3	118.15 (16)	C15—C14—C19	121.81 (18)
C5—C4—C7	121.30 (16)	C15—C14—N4	118.95 (17)
C3—C4—C7	120.54 (16)	C19—C14—N4	119.19 (15)
C4—C5—C6	121.04 (18)	C14—C15—C16	118.4 (2)
C4—C5—H5	119.5	C14—C15—H15	120.8
C6—C5—H5	119.5	C16—C15—H15	120.8
C1—C6—C5	118.50 (18)	C17—C16—C15	120.7 (2)
C1—C6—H6	120.7	C17—C16—H16	119.7
C5—C6—H6	120.7	C15—C16—H16	119.7
C4—C7—C8	110.67 (14)	C16—C17—C18	120.3 (2)
C4—C7—H7A	109.5	C16—C17—H17	119.9
C8—C7—H7A	109.5	C18—C17—H17	119.9
C4—C7—H7B	109.5	C17—C18—C19	120.1 (2)
C8—C7—H7B	109.5	C17—C18—H18	120.0
H7A—C7—H7B	108.1	C19—C18—H18	120.0
N1—C8—C7	113.30 (14)	C14—C19—C18	118.7 (2)
N1—C8—H8A	108.9	C14—C19—H19	120.6
C7—C8—H8A	108.9	C18—C19—H19	120.6
N1—C8—H8B	108.9	C12—N1—C9	122.40 (13)
C7—C8—H8B	108.9	C12—N1—C8	119.05 (14)
H8A—C8—H8B	107.7	C9—N1—C8	118.54 (14)
N3—C9—N1	118.24 (15)	C12—N2—C11	113.08 (14)
N3—C9—C10	131.12 (16)	C9—N3—H3A	110.2 (16)
N1—C9—C10	110.63 (14)	C13—N4—C11	114.58 (13)
C11—C10—C9	121.06 (15)	C13—N4—C14	123.01 (13)
C11—C10—S1	110.87 (12)	C11—N4—C14	122.39 (12)
C9—C10—S1	128.06 (12)	C10—S1—C13	91.60 (8)

F1—C1—C2—C3	−177.55 (17)	C17—C18—C19—C14	0.3 (3)
C6—C1—C2—C3	1.4 (3)	N2—C12—N1—C9	3.5 (3)
C1—C2—C3—C4	−0.1 (3)	N2—C12—N1—C8	−175.59 (17)
C2—C3—C4—C5	−1.9 (3)	N3—C9—N1—C12	175.35 (18)
C2—C3—C4—C7	179.23 (16)	C10—C9—N1—C12	−5.8 (2)
C3—C4—C5—C6	2.7 (3)	N3—C9—N1—C8	−5.6 (2)
C7—C4—C5—C6	−178.48 (17)	C10—C9—N1—C8	173.26 (14)
C2—C1—C6—C5	−0.7 (3)	C7—C8—N1—C12	−100.26 (19)
F1—C1—C6—C5	178.28 (18)	C7—C8—N1—C9	80.6 (2)
C4—C5—C6—C1	−1.4 (3)	N1—C12—N2—C11	1.3 (3)
C5—C4—C7—C8	−109.01 (19)	C10—C11—N2—C12	−3.2 (3)
C3—C4—C7—C8	69.8 (2)	N4—C11—N2—C12	175.53 (15)
C4—C7—C8—N1	−173.93 (15)	S2—C13—N4—C11	179.73 (13)
N3—C9—C10—C11	−177.3 (2)	S1—C13—N4—C11	−0.73 (19)
N1—C9—C10—C11	4.0 (2)	S2—C13—N4—C14	1.2 (3)
N3—C9—C10—S1	4.0 (3)	S1—C13—N4—C14	−179.28 (13)
N1—C9—C10—S1	−174.59 (13)	C10—C11—N4—C13	0.2 (2)
C9—C10—C11—N2	0.3 (3)	N2—C11—N4—C13	−178.63 (15)
S1—C10—C11—N2	179.18 (14)	C10—C11—N4—C14	178.81 (15)
C9—C10—C11—N4	−178.47 (15)	N2—C11—N4—C14	−0.1 (2)
S1—C10—C11—N4	0.37 (19)	C15—C14—N4—C13	76.3 (2)
C19—C14—C15—C16	1.2 (3)	C19—C14—N4—C13	−106.2 (2)
N4—C14—C15—C16	178.58 (18)	C15—C14—N4—C11	−102.1 (2)
C14—C15—C16—C17	−0.5 (4)	C19—C14—N4—C11	75.4 (2)
C15—C16—C17—C18	−0.2 (4)	C11—C10—S1—C13	−0.66 (14)
C16—C17—C18—C19	0.3 (4)	C9—C10—S1—C13	178.08 (17)
C15—C14—C19—C18	−1.1 (3)	N4—C13—S1—C10	0.78 (14)
N4—C14—C19—C18	−178.46 (17)	S2—C13—S1—C10	−179.66 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N3ⁱ	0.93	2.61	3.486 (3)	156
C19—H19···Cg3ⁱⁱ	0.93	2.74	3.637 (2)	161

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅FN₄S₂
M_r	382.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.6449 (13), 12.3780 (19), 16.546 (3)
β (°)	91.531 (3)
V (Å³)	1769.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.910, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	13207, 4047, 3442
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.119, 1.05
No. of reflections	4047
No. of parameters	238
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.24

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N3ⁱ	0.93	2.61	3.486 (3)	156.4
C19—H19···Cg3ⁱⁱ	0.93	2.74	3.637 (2)	161

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

Acknowledgements

We gratefully acknowledge the financial support of this work by the National Basic Research Program of China (2003CB114400) and the National Natural Science Foundation of China (No. 20372023).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Balkan, A., Goren, Z. & Urgan, H. (2002). Arzneim. Forsch. 52, 462–467. CAS Google Scholar
Bekhit, A. A., Fahmy, H. T. Y., Rostom, S. A. F. & Baraka, A. M. (2003). Eur. J. Med. Chem. 38, 27–34. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Danel, K., Pedersen, E. B. & Nielsen, C. (1998). J. Med. Chem. 41, 191–198. Web of Science CrossRef CAS PubMed Google Scholar
Fahmy, H. T. Y., Rostom, S. A. F., Saudi, M. N. & Zjawiony, J. K. (2003). Arch. Pharm. Pharm. Med. Chem. 336, 216–225. Web of Science CrossRef CAS Google Scholar
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885–3896. Web of Science CrossRef Google Scholar
Liang, Y., Fang, S., Mo, W. Y. & He, H. W. (2007). J. Fluorine Chem. 128, 879–884. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

6-(4-Fluoro­pheneth­yl)-7-imino-3-phenyl-2,3,6,7-tetra­hydro-1,3-thia­zolo[4,5-d]pyrimidine-2-thione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

6-(4-Fluorophenethyl)-7-imino-3-phenyl-2,3,6,7-tetrahydro-1,3-thiazolo[4,5-d]pyrimidine-2-thione