Ethyl (Z)-2-(2-fluoro-benzyl-idene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

The title compound, C(23)H(19)FN(2)O(3)S, a fused-pyrimidine derivative, displays dihedral angles between the thia-zole ring and the benzene ring and substituted benzene ring of 7.10 (14) and 3.48 (12)°, respectively. The dihydro-pyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z configuration.

Related literature

For related crystal structures, see: Hou (2009 ▶); Kulakov et al. (2009 ▶). For background to the biological properties of fused-pyrimidine derivatives, see: Alam et al. (2010 ▶); Al-Rashood & Abdel-Aziz (2010 ▶); Ashok et al. (2007 ▶); Jang et al. (2011 ▶); Wichmann et al. (1999 ▶);. Zhou et al. (2011 ▶).

Experimental

Crystal data

C23H19FN2O3S

M = 422.46

Monoclinic,

a = 9.3230 (19) Å

b = 10.170 (2) Å

c = 21.862 (4) Å

β = 96.33 (3)°

V = 2060.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.26 × 0.17 × 0.13 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.831, T max = 1.000

10963 measured reflections

4040 independent reflections

2918 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.147

S = 1.04

4040 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042899/ng5248sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042899/ng5248Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042899/ng5248Isup3.cml

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

C23H19FN2O3S	F(000) = 880
Mr = 422.46	Dx = 1.362 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.3230 (19) Å	Cell parameters from 2127 reflections
b = 10.170 (2) Å	θ = 2.5–24.0°
c = 21.862 (4) Å	µ = 0.19 mm−1
β = 96.33 (3)°	T = 293 K
V = 2060.3 (7) Å3	Prismatic, green
Z = 4	0.26 × 0.17 × 0.13 mm

Bruker SMART diffractometer	4040 independent reflections
Radiation source: fine-focus sealed tube	2918 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.831, Tmax = 1.000	k = −11→12
10963 measured reflections	l = −21→26

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0733P)2 + 0.4206P] where P = (Fo2 + 2Fc2)/3
4040 reflections	(Δ/σ)max = 0.009
273 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.17 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	0.12550 (6)	0.33812 (6)	1.02831 (3)	0.0515 (2)
N1	0.00474 (18)	0.31076 (17)	0.91699 (8)	0.0421 (4)
N2	−0.0764 (2)	0.16406 (19)	0.98954 (9)	0.0551 (5)
F1	0.46561 (19)	0.74388 (17)	0.96836 (8)	0.0873 (5)
O1	0.10315 (17)	0.47535 (17)	0.86461 (7)	0.0571 (4)
O2	−0.3636 (2)	0.0068 (2)	0.83596 (11)	0.0977 (7)
O3	−0.28690 (19)	0.1748 (2)	0.78413 (9)	0.0721 (5)
C1	0.0939 (2)	0.4181 (2)	0.91203 (10)	0.0423 (5)
C2	0.1745 (2)	0.4481 (2)	0.97289 (9)	0.0431 (5)
C3	0.0027 (2)	0.2577 (2)	0.97443 (10)	0.0455 (5)
C4	−0.0700 (2)	0.2454 (2)	0.86253 (10)	0.0476 (5)
H4	−0.1203	0.3121	0.8358	0.057*
C5	−0.1807 (2)	0.1507 (2)	0.88343 (11)	0.0499 (6)
C6	−0.1772 (2)	0.1125 (2)	0.94227 (12)	0.0536 (6)
C7	0.2703 (2)	0.5462 (2)	0.97837 (10)	0.0475 (5)
H7	0.2781	0.5930	0.9424	0.057*
C8	0.3638 (2)	0.5912 (2)	1.03149 (11)	0.0496 (6)
C9	0.3658 (3)	0.5407 (3)	1.09065 (12)	0.0632 (7)
H9	0.3031	0.4727	1.0979	0.076*
C10	0.4586 (3)	0.5889 (3)	1.13895 (13)	0.0768 (9)
H10	0.4578	0.5534	1.1781	0.092*
C11	0.5515 (3)	0.6883 (3)	1.12944 (16)	0.0795 (9)
H11	0.6140	0.7202	1.1622	0.095*
C12	0.5536 (3)	0.7414 (3)	1.07228 (15)	0.0747 (8)
H12	0.6164	0.8096	1.0657	0.090*
C13	0.4611 (3)	0.6919 (3)	1.02485 (13)	0.0588 (6)
C14	0.0385 (3)	0.1753 (3)	0.82699 (11)	0.0574 (7)
C15	0.0600 (3)	0.2140 (3)	0.76873 (13)	0.0809 (9)
H15	0.0088	0.2847	0.7504	0.097*
C16	0.1604 (5)	0.1456 (5)	0.73671 (18)	0.1075 (14)
H16	0.1754	0.1707	0.6970	0.129*
C17	0.2346 (4)	0.0434 (5)	0.7641 (2)	0.1163 (17)
H17	0.3004	−0.0013	0.7428	0.140*
C18	0.2155 (3)	0.0046 (4)	0.8219 (2)	0.1027 (13)
H18	0.2684	−0.0653	0.8402	0.123*
C19	0.1160 (3)	0.0704 (3)	0.85343 (15)	0.0768 (9)
H19	0.1014	0.0434	0.8929	0.092*
C20	−0.2869 (3)	0.1001 (3)	0.83382 (14)	0.0605 (7)
C21	−0.3860 (3)	0.1400 (4)	0.73092 (15)	0.0931 (11)
H21A	−0.3472	0.0674	0.7092	0.112*
H21B	−0.4777	0.1128	0.7439	0.112*
C22	−0.4067 (5)	0.2525 (5)	0.69102 (16)	0.1257 (15)
H22A	−0.4401	0.3254	0.7135	0.189*
H22B	−0.4769	0.2320	0.6569	0.189*
H22C	−0.3169	0.2751	0.6761	0.189*
C23	−0.2756 (3)	0.0149 (3)	0.96687 (15)	0.0743 (8)
H23A	−0.3639	0.0100	0.9399	0.111*
H23B	−0.2961	0.0418	1.0071	0.111*
H23C	−0.2300	−0.0699	0.9695	0.111*

	U11	U22	U33	U12	U13	U23
S1	0.0556 (4)	0.0553 (4)	0.0424 (3)	0.0045 (3)	−0.0004 (3)	0.0014 (3)
N1	0.0425 (10)	0.0440 (10)	0.0396 (9)	0.0018 (8)	0.0034 (7)	−0.0048 (8)
N2	0.0538 (12)	0.0497 (12)	0.0619 (13)	0.0032 (10)	0.0064 (10)	0.0065 (10)
F1	0.0901 (12)	0.0884 (12)	0.0848 (12)	−0.0292 (10)	0.0158 (9)	−0.0101 (9)
O1	0.0642 (10)	0.0621 (10)	0.0435 (9)	−0.0110 (8)	−0.0008 (7)	0.0053 (8)
O2	0.0845 (15)	0.0827 (15)	0.1215 (19)	−0.0357 (12)	−0.0082 (13)	−0.0088 (13)
O3	0.0576 (11)	0.0893 (14)	0.0668 (12)	−0.0195 (10)	−0.0052 (9)	−0.0159 (10)
C1	0.0424 (12)	0.0417 (12)	0.0423 (12)	0.0036 (9)	0.0027 (9)	−0.0044 (10)
C2	0.0434 (12)	0.0439 (12)	0.0413 (12)	0.0118 (10)	0.0023 (9)	−0.0061 (9)
C3	0.0439 (12)	0.0443 (12)	0.0487 (13)	0.0104 (10)	0.0063 (10)	0.0013 (10)
C4	0.0418 (12)	0.0527 (13)	0.0473 (12)	−0.0001 (10)	0.0004 (10)	−0.0083 (10)
C5	0.0360 (12)	0.0456 (12)	0.0684 (16)	0.0033 (10)	0.0076 (11)	−0.0087 (11)
C6	0.0433 (13)	0.0409 (12)	0.0772 (18)	0.0069 (10)	0.0091 (12)	0.0008 (12)
C7	0.0472 (12)	0.0469 (12)	0.0475 (12)	0.0075 (10)	0.0009 (10)	−0.0060 (10)
C8	0.0432 (12)	0.0501 (13)	0.0542 (14)	0.0116 (10)	−0.0009 (10)	−0.0119 (11)
C9	0.0656 (16)	0.0600 (16)	0.0605 (16)	0.0053 (13)	−0.0085 (12)	−0.0130 (12)
C10	0.081 (2)	0.082 (2)	0.0614 (17)	0.0164 (17)	−0.0211 (15)	−0.0173 (15)
C11	0.0549 (17)	0.088 (2)	0.090 (2)	0.0123 (16)	−0.0197 (15)	−0.0418 (18)
C12	0.0486 (15)	0.0779 (19)	0.095 (2)	0.0000 (14)	−0.0020 (15)	−0.0379 (17)
C13	0.0459 (13)	0.0580 (15)	0.0719 (17)	0.0036 (12)	0.0041 (12)	−0.0179 (13)
C14	0.0435 (13)	0.0694 (16)	0.0598 (15)	−0.0153 (12)	0.0084 (11)	−0.0282 (13)
C15	0.080 (2)	0.098 (2)	0.0684 (18)	−0.0322 (17)	0.0249 (15)	−0.0315 (16)
C16	0.106 (3)	0.132 (3)	0.094 (3)	−0.059 (3)	0.053 (2)	−0.055 (3)
C17	0.075 (2)	0.128 (4)	0.155 (4)	−0.037 (2)	0.056 (3)	−0.087 (3)
C18	0.0606 (19)	0.109 (3)	0.140 (3)	0.0046 (18)	0.020 (2)	−0.057 (3)
C19	0.0515 (15)	0.085 (2)	0.094 (2)	0.0080 (15)	0.0098 (14)	−0.0357 (17)
C20	0.0411 (13)	0.0565 (15)	0.0834 (19)	−0.0013 (12)	0.0050 (12)	−0.0158 (14)
C21	0.071 (2)	0.121 (3)	0.081 (2)	−0.0205 (19)	−0.0181 (17)	−0.026 (2)
C22	0.160 (4)	0.138 (4)	0.069 (2)	−0.015 (3)	−0.030 (2)	−0.018 (2)
C23	0.0620 (17)	0.0546 (16)	0.107 (2)	−0.0019 (13)	0.0147 (15)	0.0184 (15)

S1—C2	1.746 (2)	C10—C11	1.361 (4)
S1—C3	1.752 (2)	C10—H10	0.9300
N1—C3	1.369 (3)	C11—C12	1.364 (4)
N1—C1	1.384 (3)	C11—H11	0.9300
N1—C4	1.470 (3)	C12—C13	1.369 (4)
N2—C3	1.270 (3)	C12—H12	0.9300
N2—C6	1.418 (3)	C14—C15	1.368 (4)
F1—C13	1.348 (3)	C14—C19	1.379 (4)
O1—C1	1.201 (3)	C15—C16	1.413 (5)
O2—C20	1.192 (3)	C15—H15	0.9300
O3—C20	1.326 (3)	C16—C17	1.351 (6)
O3—C21	1.448 (3)	C16—H16	0.9300
C1—C2	1.486 (3)	C17—C18	1.353 (6)
C2—C7	1.336 (3)	C17—H17	0.9300
C4—C5	1.518 (3)	C18—C19	1.387 (4)
C4—C14	1.520 (3)	C18—H18	0.9300
C4—H4	0.9800	C19—H19	0.9300
C5—C6	1.341 (3)	C21—C22	1.438 (5)
C5—C20	1.478 (3)	C21—H21A	0.9700
C6—C23	1.492 (3)	C21—H21B	0.9700
C7—C8	1.447 (3)	C22—H22A	0.9600
C7—H7	0.9300	C22—H22B	0.9600
C8—C13	1.387 (4)	C22—H22C	0.9600
C8—C9	1.390 (4)	C23—H23A	0.9600
C9—C10	1.379 (4)	C23—H23B	0.9600
C9—H9	0.9300	C23—H23C	0.9600
C2—S1—C3	91.96 (11)	C13—C12—H12	120.8
C3—N1—C1	116.89 (18)	F1—C13—C12	118.0 (3)
C3—N1—C4	120.74 (18)	F1—C13—C8	118.2 (2)
C1—N1—C4	121.90 (18)	C12—C13—C8	123.8 (3)
C3—N2—C6	116.4 (2)	C15—C14—C19	119.3 (3)
C20—O3—C21	117.4 (2)	C15—C14—C4	121.0 (3)
O1—C1—N1	123.46 (19)	C19—C14—C4	119.7 (2)
O1—C1—C2	126.6 (2)	C14—C15—C16	119.5 (4)
N1—C1—C2	109.93 (19)	C14—C15—H15	120.2
C7—C2—C1	120.1 (2)	C16—C15—H15	120.2
C7—C2—S1	129.77 (17)	C17—C16—C15	119.6 (4)
C1—C2—S1	110.16 (16)	C17—C16—H16	120.2
N2—C3—N1	127.0 (2)	C15—C16—H16	120.2
N2—C3—S1	122.04 (18)	C16—C17—C18	121.7 (4)
N1—C3—S1	111.00 (16)	C16—C17—H17	119.2
N1—C4—C5	108.68 (18)	C18—C17—H17	119.2
N1—C4—C14	110.08 (17)	C17—C18—C19	119.1 (4)
C5—C4—C14	111.69 (19)	C17—C18—H18	120.4
N1—C4—H4	108.8	C19—C18—H18	120.4
C5—C4—H4	108.8	C14—C19—C18	120.9 (4)
C14—C4—H4	108.8	C14—C19—H19	119.6
C6—C5—C20	123.1 (2)	C18—C19—H19	119.6
C6—C5—C4	121.8 (2)	O2—C20—O3	122.9 (3)
C20—C5—C4	115.0 (2)	O2—C20—C5	127.2 (3)
C5—C6—N2	122.4 (2)	O3—C20—C5	109.9 (2)
C5—C6—C23	126.0 (2)	C22—C21—O3	108.9 (3)
N2—C6—C23	111.6 (2)	C22—C21—H21A	109.9
C2—C7—C8	130.2 (2)	O3—C21—H21A	109.9
C2—C7—H7	114.9	C22—C21—H21B	109.9
C8—C7—H7	114.9	O3—C21—H21B	109.9
C13—C8—C9	115.4 (2)	H21A—C21—H21B	108.3
C13—C8—C7	119.5 (2)	C21—C22—H22A	109.5
C9—C8—C7	125.1 (2)	C21—C22—H22B	109.5
C10—C9—C8	121.6 (3)	H22A—C22—H22B	109.5
C10—C9—H9	119.2	C21—C22—H22C	109.5
C8—C9—H9	119.2	H22A—C22—H22C	109.5
C11—C10—C9	120.2 (3)	H22B—C22—H22C	109.5
C11—C10—H10	119.9	C6—C23—H23A	109.5
C9—C10—H10	119.9	C6—C23—H23B	109.5
C10—C11—C12	120.5 (3)	H23A—C23—H23B	109.5
C10—C11—H11	119.7	C6—C23—H23C	109.5
C12—C11—H11	119.7	H23A—C23—H23C	109.5
C11—C12—C13	118.5 (3)	H23B—C23—H23C	109.5
C11—C12—H12	120.8
C3—N1—C1—O1	−178.3 (2)	S1—C2—C7—C8	0.6 (4)
C4—N1—C1—O1	9.5 (3)	C2—C7—C8—C13	176.4 (2)
C3—N1—C1—C2	2.4 (2)	C2—C7—C8—C9	−3.3 (4)
C4—N1—C1—C2	−169.82 (17)	C13—C8—C9—C10	0.2 (4)
O1—C1—C2—C7	−1.2 (3)	C7—C8—C9—C10	179.9 (2)
N1—C1—C2—C7	178.14 (18)	C8—C9—C10—C11	−0.1 (4)
O1—C1—C2—S1	−179.97 (19)	C9—C10—C11—C12	0.2 (4)
N1—C1—C2—S1	−0.6 (2)	C10—C11—C12—C13	−0.4 (4)
C3—S1—C2—C7	−179.4 (2)	C11—C12—C13—F1	−179.1 (2)
C3—S1—C2—C1	−0.79 (16)	C11—C12—C13—C8	0.6 (4)
C6—N2—C3—N1	−2.6 (3)	C9—C8—C13—F1	179.2 (2)
C6—N2—C3—S1	176.41 (16)	C7—C8—C13—F1	−0.5 (3)
C1—N1—C3—N2	176.1 (2)	C9—C8—C13—C12	−0.5 (4)
C4—N1—C3—N2	−11.6 (3)	C7—C8—C13—C12	179.8 (2)
C1—N1—C3—S1	−3.0 (2)	N1—C4—C14—C15	−115.2 (2)
C4—N1—C3—S1	169.30 (15)	C5—C4—C14—C15	124.0 (2)
C2—S1—C3—N2	−177.05 (19)	N1—C4—C14—C19	65.4 (3)
C2—S1—C3—N1	2.07 (16)	C5—C4—C14—C19	−55.4 (3)
C3—N1—C4—C5	19.3 (3)	C19—C14—C15—C16	0.2 (4)
C1—N1—C4—C5	−168.82 (18)	C4—C14—C15—C16	−179.2 (2)
C3—N1—C4—C14	−103.3 (2)	C14—C15—C16—C17	−0.4 (5)
C1—N1—C4—C14	68.6 (3)	C15—C16—C17—C18	−0.1 (6)
N1—C4—C5—C6	−16.0 (3)	C16—C17—C18—C19	0.8 (5)
C14—C4—C5—C6	105.6 (2)	C15—C14—C19—C18	0.4 (4)
N1—C4—C5—C20	166.70 (18)	C4—C14—C19—C18	179.8 (2)
C14—C4—C5—C20	−71.7 (2)	C17—C18—C19—C14	−0.9 (5)
C20—C5—C6—N2	−178.7 (2)	C21—O3—C20—O2	0.4 (4)
C4—C5—C6—N2	4.3 (3)	C21—O3—C20—C5	−179.5 (2)
C20—C5—C6—C23	0.5 (4)	C6—C5—C20—O2	−13.9 (4)
C4—C5—C6—C23	−176.5 (2)	C4—C5—C20—O2	163.4 (3)
C3—N2—C6—C5	6.2 (3)	C6—C5—C20—O3	166.0 (2)
C3—N2—C6—C23	−173.1 (2)	C4—C5—C20—O3	−16.8 (3)
C1—C2—C7—C8	−177.9 (2)	C20—O3—C21—C22	160.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1i	0.93	2.62	3.410 (5)	144.
C23—H23C···S1ii	0.96	2.90	3.851 (3)	173.