Ethyl 7-methyl-2-[4-(methyl­sulfan­yl)benzyl­idene]-5-[4-(methyl­sulfan­yl)phen­yl]-3-oxo-2,3-dihydro-5H-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

The title compound, C₂₅H₂₄N₂O₃S₃, was crystallized from a methanol–acetone mixture. The monoclinic structure features one mol­ecule in the asymmetric unit. The crystal packing is stabilized by π stacking.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.055
• wR factor = 0.142
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.92 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.68 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level G
PUBL017_ALERT_1_G The _publ_section_references section is missing or
            empty.

   0 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Diamond (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).

Ethyl 7-methyl-2-[4-(methylsulfanyl)benzylidene]-5-[4-(methylsulfanyl)phenyl]-3-oxo- 2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate

Crystal data

C25H24N2O3S3	F(000) = 1040
Mr = 496.67	Dx = 1.373 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 54 reflections
a = 8.771 (1) Å	θ = 7.3–19.4°
b = 12.384 (2) Å	µ = 0.34 mm^−1
c = 22.224 (6) Å	T = 297 K
β = 95.47 (2)°	Block, orange
V = 2403.1 (8) Å^3	0.32 × 0.19 × 0.14 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	Rint = 0.098
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 4.5°
φ & ω scans	h = −11→11
27621 measured reflections	k = −15→16
5484 independent reflections	l = −28→27
3683 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0477P)^2 + 1.7062P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
5484 reflections	Δρmax = 0.34 e Å^−3
298 parameters	Δρmin = −0.35 e Å^−3
0 restraints

Special details

Experimental. IR (KBr, ν, cm^-1): 2976 (C—H), 1710 (C═O), 1606 (C═N), 1541 (C═ C), 1159(C—O); ¹H NMR (CDCl₃): δ 1.22 (t, 3H, J = 7.12 Hz, ester-CH₃), 4.14 (q, 2H, J = 7.12 Hz, ester-CH₂), 2.44 (s, 3H, CH₃), 2.51 (s, 3H, SCH₃), 6.18 (s, 1H, CH), 7.17 (d, 2H, J = 8.36 Hz, 4-methylthiophenyl), 7.33 (d, 2H, J = 8.32 Hz, 4-methylthiophenyl), 7.23 (d, 2H, J = 8.28 Hz, 4-methylthiophenyl), 7.38 (d, 2H, J = 8.36 Hz, 4-methylthiophenyl), 7.71 (s, 1H, exocyclic CH); MS (m/z, %): 497(M⁺+1, 100), 496 (M⁺, 90), 451 (31), 373 (75), 362 (10), 180 (10), 154 (55), 136 (40).

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.86396 (10)	0.88084 (9)	0.42526 (3)	0.0689 (3)
S2	0.62540 (8)	0.84135 (6)	0.03547 (3)	0.04253 (19)
S3	1.06954 (9)	1.15004 (7)	−0.16769 (3)	0.0530 (2)
C1	0.8001 (5)	0.9946 (4)	0.46511 (14)	0.0931 (14)
C2	0.7462 (3)	0.8846 (2)	0.35595 (11)	0.0440 (7)
C3	0.6559 (3)	0.9718 (2)	0.33637 (11)	0.0467 (7)
C4	0.5606 (3)	0.9648 (2)	0.28275 (11)	0.0401 (6)
C5	0.5562 (3)	0.87206 (19)	0.24804 (10)	0.0319 (5)
C6	0.6520 (3)	0.7873 (2)	0.26693 (11)	0.0379 (6)
C7	0.7464 (3)	0.7931 (2)	0.32032 (12)	0.0437 (6)
C8	0.4394 (3)	0.8608 (2)	0.19315 (10)	0.0319 (5)
C9	0.3641 (3)	0.7508 (2)	0.19020 (10)	0.0347 (5)
C10	0.3789 (3)	0.6812 (2)	0.14451 (11)	0.0418 (6)
C11	0.3034 (4)	0.5734 (3)	0.13666 (15)	0.0670 (10)
C12	0.2817 (3)	0.7209 (2)	0.24253 (11)	0.0394 (6)
C13	0.1814 (4)	0.7879 (3)	0.33078 (14)	0.0603 (9)
C14	0.3037 (5)	0.7928 (3)	0.38259 (15)	0.0781 (11)
C15	0.5226 (3)	0.7987 (2)	0.09496 (10)	0.0368 (6)
C16	0.5678 (3)	0.9790 (2)	0.12197 (11)	0.0369 (6)
C17	0.6443 (3)	0.9714 (2)	0.06536 (10)	0.0369 (6)
C18	0.7141 (3)	1.0579 (2)	0.04479 (11)	0.0402 (6)
C19	0.7963 (3)	1.0741 (2)	−0.00830 (11)	0.0386 (6)
C20	0.8704 (3)	1.1720 (2)	−0.01444 (13)	0.0488 (7)
C21	0.9526 (3)	1.1926 (2)	−0.06285 (13)	0.0509 (7)
C22	0.9615 (3)	1.1155 (2)	−0.10787 (11)	0.0409 (6)
C23	0.8862 (3)	1.0187 (2)	−0.10302 (11)	0.0467 (7)
C24	0.8053 (3)	0.9981 (2)	−0.05391 (11)	0.0447 (6)
C25	1.0622 (4)	1.0309 (3)	−0.21280 (13)	0.0626 (9)
N1	0.4665 (3)	0.70410 (18)	0.09631 (9)	0.0458 (6)
N2	0.5095 (2)	0.87976 (16)	0.13606 (8)	0.0328 (5)
O1	0.2512 (3)	0.63089 (16)	0.25734 (9)	0.0601 (6)
O2	0.2485 (2)	0.80790 (15)	0.27444 (8)	0.0455 (5)
O3	0.5565 (2)	1.05888 (15)	0.15221 (8)	0.0488 (5)
H1A	0.8201	1.0595	0.4436	0.140*
H1B	0.8539	0.9972	0.5048	0.140*
H1C	0.6922	0.9884	0.4684	0.140*
H3	0.6590	1.0350	0.3591	0.056*
H4	0.4991	1.0233	0.2701	0.048*
H6	0.6528	0.7254	0.2433	0.045*
H7	0.8102	0.7354	0.3323	0.052*
H8	0.3595	0.9153	0.1963	0.038*
H11A	0.2548	0.5559	0.1723	0.101*
H11B	0.3790	0.5196	0.1303	0.101*
H11C	0.2280	0.5754	0.1024	0.101*
H13A	0.1332	0.7174	0.3294	0.072*
H13B	0.1036	0.8417	0.3362	0.072*
H14A	0.3759	0.7355	0.3789	0.117*
H14B	0.2581	0.7850	0.4199	0.117*
H14C	0.3555	0.8611	0.3822	0.117*
H18	0.7093	1.1190	0.0689	0.048*
H20	0.8644	1.2249	0.0149	0.059*
H21	1.0024	1.2585	−0.0655	0.061*
H23	0.8898	0.9668	−0.1331	0.056*
H24	0.7559	0.9321	−0.0513	0.054*
H25A	1.1061	0.9718	−0.1892	0.094*
H25B	1.1190	1.0422	−0.2471	0.094*
H25C	0.9575	1.0146	−0.2265	0.094*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0652 (5)	0.1003 (7)	0.0381 (4)	−0.0187 (5)	−0.0107 (4)	0.0107 (4)
S2	0.0550 (4)	0.0436 (4)	0.0309 (3)	−0.0006 (3)	0.0142 (3)	−0.0017 (3)
S3	0.0527 (4)	0.0682 (5)	0.0398 (4)	−0.0084 (4)	0.0142 (3)	0.0130 (3)
C1	0.096 (3)	0.145 (4)	0.0375 (18)	−0.023 (3)	0.0018 (18)	−0.019 (2)
C2	0.0412 (15)	0.0607 (18)	0.0299 (12)	−0.0109 (13)	0.0032 (11)	0.0085 (12)
C3	0.0555 (18)	0.0519 (17)	0.0335 (13)	−0.0073 (14)	0.0084 (12)	−0.0094 (12)
C4	0.0459 (15)	0.0405 (15)	0.0344 (13)	0.0023 (12)	0.0072 (11)	−0.0012 (11)
C5	0.0335 (13)	0.0348 (13)	0.0287 (11)	−0.0036 (10)	0.0098 (10)	0.0019 (10)
C6	0.0415 (14)	0.0364 (14)	0.0364 (13)	−0.0018 (11)	0.0074 (11)	0.0021 (11)
C7	0.0405 (15)	0.0459 (16)	0.0445 (15)	0.0014 (12)	0.0032 (12)	0.0121 (12)
C8	0.0334 (13)	0.0356 (14)	0.0277 (11)	0.0014 (10)	0.0089 (10)	0.0024 (10)
C9	0.0333 (13)	0.0364 (14)	0.0346 (12)	−0.0017 (11)	0.0042 (10)	0.0015 (10)
C10	0.0495 (16)	0.0378 (15)	0.0389 (13)	−0.0051 (12)	0.0089 (12)	−0.0004 (11)
C11	0.096 (3)	0.0502 (19)	0.0577 (19)	−0.0246 (18)	0.0243 (18)	−0.0131 (15)
C12	0.0374 (14)	0.0408 (16)	0.0411 (14)	−0.0047 (12)	0.0089 (11)	−0.0009 (11)
C13	0.073 (2)	0.0501 (18)	0.065 (2)	−0.0106 (16)	0.0449 (17)	−0.0086 (15)
C14	0.116 (3)	0.070 (2)	0.0522 (19)	0.007 (2)	0.026 (2)	0.0071 (17)
C15	0.0431 (15)	0.0403 (15)	0.0276 (12)	0.0027 (12)	0.0067 (10)	0.0012 (10)
C16	0.0373 (14)	0.0429 (15)	0.0311 (12)	−0.0002 (12)	0.0060 (10)	0.0021 (11)
C17	0.0407 (14)	0.0403 (15)	0.0304 (12)	0.0031 (12)	0.0069 (10)	0.0030 (11)
C18	0.0454 (15)	0.0437 (15)	0.0322 (12)	0.0029 (12)	0.0083 (11)	0.0009 (11)
C19	0.0409 (14)	0.0426 (15)	0.0331 (13)	0.0034 (12)	0.0078 (11)	0.0067 (11)
C20	0.0580 (18)	0.0452 (17)	0.0452 (15)	−0.0025 (14)	0.0161 (13)	−0.0011 (12)
C21	0.0573 (18)	0.0467 (17)	0.0512 (16)	−0.0065 (14)	0.0177 (14)	0.0066 (13)
C22	0.0378 (14)	0.0518 (17)	0.0337 (13)	0.0042 (12)	0.0063 (11)	0.0132 (12)
C23	0.0559 (17)	0.0517 (17)	0.0341 (13)	−0.0028 (14)	0.0130 (12)	0.0012 (12)
C24	0.0513 (16)	0.0450 (16)	0.0395 (14)	−0.0071 (13)	0.0134 (12)	0.0045 (12)
C25	0.062 (2)	0.087 (3)	0.0426 (16)	−0.0145 (18)	0.0212 (14)	−0.0033 (16)
N1	0.0610 (15)	0.0412 (13)	0.0375 (12)	−0.0044 (11)	0.0167 (11)	−0.0059 (10)
N2	0.0382 (11)	0.0334 (11)	0.0277 (10)	−0.0011 (9)	0.0078 (8)	0.0005 (8)
O1	0.0828 (16)	0.0419 (12)	0.0609 (13)	−0.0110 (11)	0.0343 (11)	−0.0011 (10)
O2	0.0535 (11)	0.0406 (11)	0.0457 (10)	−0.0041 (9)	0.0223 (9)	−0.0027 (8)
O3	0.0682 (13)	0.0360 (10)	0.0457 (10)	−0.0069 (9)	0.0242 (9)	−0.0058 (8)

Geometric parameters (Å, º)

S1—C2	1.770 (3)	C19—C20	1.389 (4)
S1—C1	1.783 (5)	C19—C24	1.391 (4)
S2—C17	1.744 (3)	C20—C21	1.376 (4)
S2—C15	1.752 (2)	C21—C22	1.391 (4)
S3—C22	1.759 (3)	C22—C23	1.377 (4)
S3—C25	1.781 (3)	C23—C24	1.382 (4)
C2—C7	1.383 (4)	C1—H1A	0.9600
C2—C3	1.383 (4)	C1—H1B	0.9600
C3—C4	1.390 (4)	C1—H1C	0.9600
C4—C5	1.382 (3)	C3—H3	0.9300
C5—C6	1.384 (3)	C4—H4	0.9300
C5—C8	1.521 (3)	C6—H6	0.9300
C6—C7	1.382 (4)	C7—H7	0.9300
C8—N2	1.481 (3)	C8—H8	0.9800
C8—C9	1.513 (3)	C11—H11A	0.9600
C9—C10	1.348 (3)	C11—H11B	0.9600
C9—C12	1.475 (3)	C11—H11C	0.9600
C10—N1	1.406 (3)	C13—H13A	0.9700
C10—C11	1.493 (4)	C13—H13B	0.9700
C12—O1	1.200 (3)	C14—H14A	0.9600
C12—O2	1.337 (3)	C14—H14B	0.9600
C13—O2	1.455 (3)	C14—H14C	0.9600
C13—C14	1.497 (5)	C18—H18	0.9300
C15—N1	1.273 (3)	C20—H20	0.9300
C15—N2	1.369 (3)	C21—H21	0.9300
C16—O3	1.205 (3)	C23—H23	0.9300
C16—N2	1.379 (3)	C24—H24	0.9300
C16—C17	1.485 (3)	C25—H25A	0.9600
C17—C18	1.336 (4)	C25—H25B	0.9600
C18—C19	1.455 (3)	C25—H25C	0.9600
C2—S1—C1	103.08 (17)	S1—C1—H1A	109.5
C17—S2—C15	91.56 (12)	S1—C1—H1B	109.5
C22—S3—C25	103.35 (14)	H1A—C1—H1B	109.5
C7—C2—C3	119.5 (2)	S1—C1—H1C	109.5
C7—C2—S1	116.3 (2)	H1A—C1—H1C	109.5
C3—C2—S1	124.2 (2)	H1B—C1—H1C	109.5
C2—C3—C4	120.0 (3)	C2—C3—H3	120.0
C5—C4—C3	120.8 (3)	C4—C3—H3	120.0
C4—C5—C6	118.5 (2)	C5—C4—H4	119.6
C4—C5—C8	120.3 (2)	C3—C4—H4	119.6
C6—C5—C8	121.0 (2)	C7—C6—H6	119.4
C7—C6—C5	121.1 (2)	C5—C6—H6	119.4
C6—C7—C2	120.0 (3)	C6—C7—H7	120.0
N2—C8—C9	108.73 (18)	C2—C7—H7	120.0
N2—C8—C5	111.70 (18)	N2—C8—H8	108.1
C9—C8—C5	111.97 (19)	C9—C8—H8	108.1
C10—C9—C12	121.6 (2)	C5—C8—H8	108.1
C10—C9—C8	122.4 (2)	C10—C11—H11A	109.5
C12—C9—C8	115.9 (2)	C10—C11—H11B	109.5
C9—C10—N1	123.0 (2)	H11A—C11—H11B	109.5
C9—C10—C11	125.9 (2)	C10—C11—H11C	109.5
N1—C10—C11	111.1 (2)	H11A—C11—H11C	109.5
O1—C12—O2	122.5 (2)	H11B—C11—H11C	109.5
O1—C12—C9	126.1 (2)	O2—C13—H13A	109.7
O2—C12—C9	111.4 (2)	C14—C13—H13A	109.7
O2—C13—C14	109.6 (3)	O2—C13—H13B	109.7
N1—C15—N2	127.0 (2)	C14—C13—H13B	109.7
N1—C15—S2	121.56 (19)	H13A—C13—H13B	108.2
N2—C15—S2	111.43 (18)	C13—C14—H14A	109.5
O3—C16—N2	123.5 (2)	C13—C14—H14B	109.5
O3—C16—C17	126.4 (2)	H14A—C14—H14B	109.5
N2—C16—C17	110.1 (2)	C13—C14—H14C	109.5
C18—C17—C16	119.9 (2)	H14A—C14—H14C	109.5
C18—C17—S2	129.8 (2)	H14B—C14—H14C	109.5
C16—C17—S2	110.34 (18)	C17—C18—H18	114.1
C17—C18—C19	131.9 (3)	C19—C18—H18	114.1
C20—C19—C24	117.3 (2)	C21—C20—H20	119.2
C20—C19—C18	118.3 (2)	C19—C20—H20	119.2
C24—C19—C18	124.4 (2)	C20—C21—H21	119.8
C21—C20—C19	121.6 (3)	C22—C21—H21	119.8
C20—C21—C22	120.3 (3)	C22—C23—H23	119.7
C23—C22—C21	118.7 (2)	C24—C23—H23	119.7
C23—C22—S3	124.7 (2)	C23—C24—H24	119.3
C21—C22—S3	116.6 (2)	C19—C24—H24	119.3
C22—C23—C24	120.6 (3)	S3—C25—H25A	109.5
C23—C24—C19	121.4 (3)	S3—C25—H25B	109.5
C15—N1—C10	116.4 (2)	H25A—C25—H25B	109.5
C15—N2—C16	116.4 (2)	S3—C25—H25C	109.5
C15—N2—C8	121.6 (2)	H25A—C25—H25C	109.5
C16—N2—C8	121.97 (19)	H25B—C25—H25C	109.5
C12—O2—C13	116.5 (2)