(Z)-Ethyl 2-(2,4-dimethyl-benzyl-idene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

In the title compound, C(25)H(24)N(2)O(3)S, the dihedral angles between the thia-zole ring and the phenyl and substituted benzene rings are 84.91 (11) and 11.58 (10)°, respectively. The dihydro-pyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z configuration.

Related literature

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

Experimental

Crystal data

C25H24N2O3S

M = 432.52

Monoclinic,

a = 9.690 (5) Å

b = 10.620 (5) Å

c = 21.692 (12) Å

β = 90.682 (10)°

V = 2232 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.32 × 0.27 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.675, T max = 1.000

8761 measured reflections

4257 independent reflections

3096 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.155

S = 1.01

4257 reflections

284 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.26 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/S1600536811052925/rn2098sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052925/rn2098Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052925/rn2098Isup3.cml

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

C25H24N2O3S	F(000) = 912
Mr = 432.52	Dx = 1.287 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.690 (5) Å	Cell parameters from 2729 reflections
b = 10.620 (5) Å	θ = 5.4–56.3°
c = 21.692 (12) Å	µ = 0.17 mm−1
β = 90.682 (10)°	T = 293 K
V = 2232 (2) Å3	Prismatic, green
Z = 4	0.32 × 0.27 × 0.16 mm

Bruker SMART CCD area-detector diffractometer	4257 independent reflections
Radiation source: fine-focus sealed tube	3096 reflections with I > 2σ(I)
graphite	Rint = 0.026
phi and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.675, Tmax = 1.000	k = −13→11
8761 measured reflections	l = −15→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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0949P)2] where P = (Fo2 + 2Fc2)/3
4257 reflections	(Δ/σ)max = 0.003
284 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.26 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	0.39630 (6)	0.68577 (5)	1.02581 (2)	0.0468 (2)
N1	0.51571 (17)	0.71961 (14)	0.92082 (7)	0.0387 (4)
N2	0.58867 (19)	0.85690 (16)	1.00033 (8)	0.0473 (4)
O1	0.43929 (16)	0.55550 (13)	0.86185 (6)	0.0527 (4)
O2	0.8683 (2)	1.0158 (2)	0.86481 (10)	0.0999 (7)
O3	0.78414 (18)	0.86963 (17)	0.80152 (7)	0.0651 (5)
C1	0.4398 (2)	0.61190 (18)	0.91047 (9)	0.0397 (5)
C2	0.3609 (2)	0.57762 (18)	0.96664 (9)	0.0402 (5)
C3	0.5139 (2)	0.76745 (18)	0.97952 (9)	0.0412 (5)
C4	0.6868 (2)	0.90740 (19)	0.95937 (10)	0.0472 (5)
C5	0.6901 (2)	0.87651 (19)	0.89920 (10)	0.0461 (5)
C6	0.5836 (2)	0.78885 (18)	0.87051 (9)	0.0422 (5)
H6	0.6312	0.7281	0.8442	0.051*
C7	0.4768 (2)	0.8581 (2)	0.83166 (9)	0.0440 (5)
C8	0.4347 (3)	0.8122 (2)	0.77469 (10)	0.0634 (7)
H8	0.4738	0.7389	0.7592	0.076*
C9	0.3338 (3)	0.8758 (3)	0.74073 (11)	0.0804 (9)
H9	0.3056	0.8445	0.7026	0.097*
C10	0.2761 (3)	0.9832 (3)	0.76279 (13)	0.0779 (8)
H10	0.2089	1.0253	0.7398	0.093*
C11	0.3176 (3)	1.0286 (3)	0.81878 (13)	0.0758 (8)
H11	0.2780	1.1018	0.8341	0.091*
C12	0.4174 (3)	0.9670 (2)	0.85291 (11)	0.0588 (6)
H12	0.4451	0.9996	0.8909	0.071*
C13	0.7847 (3)	0.9961 (2)	0.99124 (12)	0.0617 (6)
H13A	0.8750	0.9871	0.9741	0.093*
H13B	0.7883	0.9770	1.0345	0.093*
H13C	0.7533	1.0811	0.9855	0.093*
C14	0.7908 (2)	0.9298 (2)	0.85547 (12)	0.0584 (6)
C15	0.8700 (3)	0.9143 (3)	0.75156 (13)	0.0813 (9)
H15A	0.9639	0.9276	0.7661	0.098*
H15B	0.8346	0.9933	0.7354	0.098*
C16	0.8664 (4)	0.8162 (4)	0.70314 (14)	0.1146 (14)
H16A	0.9010	0.7385	0.7198	0.172*
H16B	0.9227	0.8420	0.6693	0.172*
H16C	0.7730	0.8045	0.6889	0.172*
C17	0.2755 (2)	0.47861 (18)	0.96532 (9)	0.0441 (5)
H17	0.2744	0.4352	0.9281	0.053*
C18	0.1845 (2)	0.42670 (18)	1.01130 (9)	0.0431 (5)
C19	0.0866 (2)	0.33502 (19)	0.99376 (10)	0.0473 (5)
C20	−0.0026 (2)	0.2895 (2)	1.03827 (11)	0.0540 (6)
H20	−0.0680	0.2298	1.0265	0.065*
C21	0.0007 (2)	0.3284 (2)	1.09903 (11)	0.0536 (6)
C22	0.0988 (3)	0.4159 (2)	1.11590 (11)	0.0581 (6)
H22	0.1048	0.4426	1.1567	0.070*
C23	0.1885 (2)	0.4647 (2)	1.07309 (10)	0.0531 (6)
H23	0.2533	0.5243	1.0856	0.064*
C24	0.0761 (3)	0.2857 (2)	0.92891 (11)	0.0661 (7)
H24A	0.0026	0.2253	0.9261	0.099*
H24B	0.1615	0.2461	0.9180	0.099*
H24C	0.0575	0.3541	0.9011	0.099*
C25	−0.1005 (3)	0.2774 (3)	1.14450 (13)	0.0756 (8)
H25A	−0.1877	0.3191	1.1390	0.113*
H25B	−0.0666	0.2920	1.1856	0.113*
H25C	−0.1121	0.1886	1.1380	0.113*

	U11	U22	U33	U12	U13	U23
S1	0.0540 (4)	0.0431 (3)	0.0435 (3)	−0.0012 (2)	0.0112 (2)	−0.0006 (2)
N1	0.0400 (10)	0.0354 (8)	0.0408 (8)	−0.0022 (7)	0.0049 (7)	0.0019 (7)
N2	0.0497 (11)	0.0405 (9)	0.0519 (10)	−0.0045 (8)	0.0026 (8)	−0.0055 (8)
O1	0.0612 (10)	0.0505 (8)	0.0468 (8)	−0.0109 (8)	0.0111 (7)	−0.0067 (7)
O2	0.0972 (16)	0.0951 (15)	0.1080 (16)	−0.0585 (13)	0.0217 (13)	−0.0015 (12)
O3	0.0577 (11)	0.0771 (11)	0.0608 (10)	−0.0177 (9)	0.0164 (8)	0.0117 (9)
C1	0.0376 (12)	0.0378 (11)	0.0438 (10)	0.0017 (9)	0.0021 (9)	0.0017 (8)
C2	0.0400 (12)	0.0369 (10)	0.0439 (10)	0.0044 (9)	0.0060 (9)	0.0021 (8)
C3	0.0415 (12)	0.0366 (10)	0.0456 (10)	0.0046 (9)	0.0022 (9)	−0.0005 (8)
C4	0.0413 (12)	0.0371 (11)	0.0632 (13)	−0.0003 (9)	−0.0019 (10)	−0.0001 (9)
C5	0.0373 (12)	0.0406 (11)	0.0603 (13)	−0.0037 (9)	0.0015 (10)	0.0049 (9)
C6	0.0418 (12)	0.0397 (10)	0.0452 (10)	−0.0054 (9)	0.0100 (9)	0.0007 (8)
C7	0.0407 (12)	0.0499 (12)	0.0415 (10)	−0.0111 (10)	0.0068 (9)	0.0074 (9)
C8	0.0696 (18)	0.0719 (16)	0.0489 (12)	−0.0138 (14)	0.0042 (12)	−0.0001 (11)
C9	0.081 (2)	0.114 (2)	0.0459 (13)	−0.025 (2)	−0.0126 (13)	0.0155 (15)
C10	0.0650 (18)	0.099 (2)	0.0694 (17)	−0.0022 (17)	−0.0061 (14)	0.0363 (16)
C11	0.0722 (19)	0.0745 (18)	0.0805 (18)	0.0164 (15)	−0.0016 (15)	0.0167 (14)
C12	0.0576 (15)	0.0614 (15)	0.0575 (13)	0.0065 (12)	−0.0022 (11)	0.0037 (11)
C13	0.0550 (15)	0.0507 (13)	0.0792 (16)	−0.0102 (11)	−0.0052 (12)	−0.0043 (12)
C14	0.0442 (14)	0.0568 (14)	0.0743 (16)	−0.0075 (12)	0.0021 (12)	0.0128 (12)
C15	0.0662 (18)	0.104 (2)	0.0741 (17)	−0.0152 (16)	0.0208 (14)	0.0375 (16)
C16	0.136 (3)	0.149 (3)	0.0596 (17)	−0.023 (3)	0.036 (2)	0.0160 (19)
C17	0.0451 (12)	0.0391 (11)	0.0481 (11)	0.0002 (9)	0.0053 (9)	0.0026 (9)
C18	0.0418 (12)	0.0353 (10)	0.0522 (11)	0.0026 (9)	0.0071 (9)	0.0063 (9)
C19	0.0460 (13)	0.0367 (10)	0.0593 (12)	0.0020 (9)	0.0045 (10)	0.0072 (9)
C20	0.0431 (13)	0.0434 (12)	0.0756 (15)	−0.0036 (10)	0.0054 (11)	0.0103 (11)
C21	0.0441 (14)	0.0498 (13)	0.0672 (14)	0.0066 (11)	0.0131 (11)	0.0167 (11)
C22	0.0598 (15)	0.0613 (14)	0.0533 (13)	−0.0009 (12)	0.0116 (11)	0.0082 (11)
C23	0.0547 (14)	0.0499 (12)	0.0548 (12)	−0.0096 (11)	0.0084 (10)	0.0041 (10)
C24	0.0727 (18)	0.0569 (14)	0.0688 (15)	−0.0175 (13)	0.0074 (13)	−0.0034 (12)
C25	0.0597 (17)	0.0840 (18)	0.0836 (18)	−0.0012 (15)	0.0216 (14)	0.0293 (15)

S1—C2	1.753 (2)	C12—H12	0.9300
S1—C3	1.757 (2)	C13—H13A	0.9600
N1—C3	1.371 (3)	C13—H13B	0.9600
N1—C1	1.377 (3)	C13—H13C	0.9600
N1—C6	1.477 (2)	C15—C16	1.480 (4)
N2—C3	1.274 (3)	C15—H15A	0.9700
N2—C4	1.415 (3)	C15—H15B	0.9700
O1—C1	1.213 (2)	C16—H16A	0.9600
O2—C14	1.198 (3)	C16—H16B	0.9600
O3—C14	1.334 (3)	C16—H16C	0.9600
O3—C15	1.454 (3)	C17—C18	1.448 (3)
C1—C2	1.491 (3)	C17—H17	0.9300
C2—C17	1.338 (3)	C18—C23	1.400 (3)
C4—C5	1.347 (3)	C18—C19	1.409 (3)
C4—C13	1.500 (3)	C19—C20	1.390 (3)
C5—C14	1.481 (3)	C19—C24	1.504 (3)
C5—C6	1.518 (3)	C20—C21	1.381 (3)
C6—C7	1.517 (3)	C20—H20	0.9300
C6—H6	0.9800	C21—C22	1.376 (3)
C7—C12	1.374 (3)	C21—C25	1.501 (3)
C7—C8	1.385 (3)	C22—C23	1.380 (3)
C8—C9	1.392 (4)	C22—H22	0.9300
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.360 (4)	C24—H24A	0.9600
C9—H9	0.9300	C24—H24B	0.9600
C10—C11	1.363 (4)	C24—H24C	0.9600
C10—H10	0.9300	C25—H25A	0.9600
C11—C12	1.377 (3)	C25—H25B	0.9600
C11—H11	0.9300	C25—H25C	0.9600
C2—S1—C3	91.59 (10)	H13B—C13—H13C	109.5
C3—N1—C1	116.53 (16)	O2—C14—O3	122.5 (2)
C3—N1—C6	120.82 (16)	O2—C14—C5	126.8 (2)
C1—N1—C6	122.33 (16)	O3—C14—C5	110.7 (2)
C3—N2—C4	116.34 (17)	O3—C15—C16	106.9 (2)
C14—O3—C15	118.4 (2)	O3—C15—H15A	110.3
O1—C1—N1	123.26 (18)	C16—C15—H15A	110.3
O1—C1—C2	126.39 (19)	O3—C15—H15B	110.3
N1—C1—C2	110.34 (16)	C16—C15—H15B	110.3
C17—C2—C1	119.81 (18)	H15A—C15—H15B	108.6
C17—C2—S1	130.25 (16)	C15—C16—H16A	109.5
C1—C2—S1	109.90 (14)	C15—C16—H16B	109.5
N2—C3—N1	126.29 (19)	H16A—C16—H16B	109.5
N2—C3—S1	122.38 (16)	C15—C16—H16C	109.5
N1—C3—S1	111.30 (15)	H16A—C16—H16C	109.5
C5—C4—N2	122.71 (19)	H16B—C16—H16C	109.5
C5—C4—C13	125.3 (2)	C2—C17—C18	131.74 (19)
N2—C4—C13	112.00 (19)	C2—C17—H17	114.1
C4—C5—C14	123.4 (2)	C18—C17—H17	114.1
C4—C5—C6	121.52 (19)	C23—C18—C19	117.94 (19)
C14—C5—C6	114.95 (19)	C23—C18—C17	122.7 (2)
N1—C6—C7	110.19 (17)	C19—C18—C17	119.39 (19)
N1—C6—C5	108.00 (16)	C20—C19—C18	118.4 (2)
C7—C6—C5	112.74 (17)	C20—C19—C24	119.5 (2)
N1—C6—H6	108.6	C18—C19—C24	122.1 (2)
C7—C6—H6	108.6	C21—C20—C19	123.4 (2)
C5—C6—H6	108.6	C21—C20—H20	118.3
C12—C7—C8	118.4 (2)	C19—C20—H20	118.3
C12—C7—C6	120.47 (18)	C22—C21—C20	117.6 (2)
C8—C7—C6	121.1 (2)	C22—C21—C25	121.6 (2)
C7—C8—C9	119.9 (3)	C20—C21—C25	120.7 (2)
C7—C8—H8	120.0	C21—C22—C23	120.9 (2)
C9—C8—H8	120.0	C21—C22—H22	119.6
C10—C9—C8	120.7 (3)	C23—C22—H22	119.6
C10—C9—H9	119.7	C22—C23—C18	121.7 (2)
C8—C9—H9	119.7	C22—C23—H23	119.1
C9—C10—C11	119.5 (3)	C18—C23—H23	119.1
C9—C10—H10	120.3	C19—C24—H24A	109.5
C11—C10—H10	120.3	C19—C24—H24B	109.5
C10—C11—C12	120.6 (3)	H24A—C24—H24B	109.5
C10—C11—H11	119.7	C19—C24—H24C	109.5
C12—C11—H11	119.7	H24A—C24—H24C	109.5
C7—C12—C11	120.9 (2)	H24B—C24—H24C	109.5
C7—C12—H12	119.5	C21—C25—H25A	109.5
C11—C12—H12	119.5	C21—C25—H25B	109.5
C4—C13—H13A	109.5	H25A—C25—H25B	109.5
C4—C13—H13B	109.5	C21—C25—H25C	109.5
H13A—C13—H13B	109.5	H25A—C25—H25C	109.5
C4—C13—H13C	109.5	H25B—C25—H25C	109.5
H13A—C13—H13C	109.5
C3—N1—C1—O1	−175.24 (19)	N1—C6—C7—C8	−102.7 (2)
C6—N1—C1—O1	11.3 (3)	C5—C6—C7—C8	136.6 (2)
C3—N1—C1—C2	5.0 (2)	C12—C7—C8—C9	−0.5 (3)
C6—N1—C1—C2	−168.54 (17)	C6—C7—C8—C9	178.3 (2)
O1—C1—C2—C17	−2.7 (3)	C7—C8—C9—C10	0.2 (4)
N1—C1—C2—C17	177.07 (17)	C8—C9—C10—C11	−0.1 (4)
O1—C1—C2—S1	179.15 (18)	C9—C10—C11—C12	0.2 (4)
N1—C1—C2—S1	−1.1 (2)	C8—C7—C12—C11	0.6 (3)
C3—S1—C2—C17	−180.0 (2)	C6—C7—C12—C11	−178.1 (2)
C3—S1—C2—C1	−2.08 (15)	C10—C11—C12—C7	−0.5 (4)
C4—N2—C3—N1	−2.9 (3)	C15—O3—C14—O2	−2.9 (4)
C4—N2—C3—S1	174.98 (15)	C15—O3—C14—C5	176.3 (2)
C1—N1—C3—N2	171.51 (19)	C4—C5—C14—O2	−10.0 (4)
C6—N1—C3—N2	−14.9 (3)	C6—C5—C14—O2	166.5 (2)
C1—N1—C3—S1	−6.6 (2)	C4—C5—C14—O3	170.8 (2)
C6—N1—C3—S1	166.99 (14)	C6—C5—C14—O3	−12.6 (3)
C2—S1—C3—N2	−173.40 (18)	C14—O3—C15—C16	167.7 (3)
C2—S1—C3—N1	4.81 (15)	C1—C2—C17—C18	−177.9 (2)
C3—N2—C4—C5	9.0 (3)	S1—C2—C17—C18	−0.2 (4)
C3—N2—C4—C13	−170.39 (18)	C2—C17—C18—C23	−11.2 (4)
N2—C4—C5—C14	179.09 (19)	C2—C17—C18—C19	168.2 (2)
C13—C4—C5—C14	−1.6 (4)	C23—C18—C19—C20	1.5 (3)
N2—C4—C5—C6	2.8 (3)	C17—C18—C19—C20	−177.96 (19)
C13—C4—C5—C6	−178.0 (2)	C23—C18—C19—C24	−178.5 (2)
C3—N1—C6—C7	−100.3 (2)	C17—C18—C19—C24	2.0 (3)
C1—N1—C6—C7	73.0 (2)	C18—C19—C20—C21	−0.8 (3)
C3—N1—C6—C5	23.3 (3)	C24—C19—C20—C21	179.2 (2)
C1—N1—C6—C5	−163.48 (17)	C19—C20—C21—C22	−0.6 (3)
C4—C5—C6—N1	−17.7 (3)	C19—C20—C21—C25	178.7 (2)
C14—C5—C6—N1	165.70 (18)	C20—C21—C22—C23	1.3 (3)
C4—C5—C6—C7	104.3 (2)	C25—C21—C22—C23	−178.0 (2)
C14—C5—C6—C7	−72.3 (2)	C21—C22—C23—C18	−0.6 (4)
N1—C6—C7—C12	76.0 (2)	C19—C18—C23—C22	−0.9 (3)
C5—C6—C7—C12	−44.7 (3)	C17—C18—C23—C22	178.6 (2)