(2E)-2-(2,4-Di­chloro­benzyl­idene)-6,7-di­hydro-2H-thia­zolo­[3,2-a]­pyrimidin-3(5H)-one

The title compound, C₁₃H₁₀Cl₂N₂OS, was synthesized by mixing 2,4-di­chloro­benz­aldehyde, ethyl chloro­acetate and tetra­hydro­pyrimidine-2-thione in ethanol. The nearly planar thia­zoline ring is fused to a di­hydro­pyrimidine ring, which has a sofa conformation. The mol­ecules are connected through weak C—H...N, C—H...O and C—H...Cl interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.094
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(2E)-2-(2,4-Dichlorobenzylidene)-6,7-dihydro-2H-thiazolo[3,2-a]pyrimidin- 3(5H)-one

Crystal data

C13H10Cl2N2OS	F(000) = 640
Mr = 313.19	Dx = 1.555 Mg m^−3
Monoclinic, P21/c	Melting point = 437–439 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.155 (2) Å	Cell parameters from 791 reflections
b = 9.676 (4) Å	θ = 3.6–26.5°
c = 22.507 (8) Å	µ = 0.63 mm^−1
β = 93.543 (6)°	T = 293 K
V = 1337.8 (8) Å^3	Block cut from needle, yellow
Z = 4	0.28 × 0.26 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer	2841 independent reflections
Radiation source: fine-focus sealed tube	2191 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 26.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→7
Tmin = 0.820, Tmax = 0.881	k = −12→12
7749 measured reflections	l = −19→28

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0406P)^2 + 0.4345P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.27 e Å^−3
2841 reflections	Δρmin = −0.20 e Å^−3
172 parameters

Special details

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	0.14843 (10)	0.52038 (6)	0.40692 (2)	0.04772 (18)
Cl1	0.90193 (10)	0.15696 (7)	0.41912 (3)	0.0606 (2)
Cl2	0.59274 (12)	0.05369 (7)	0.63163 (3)	0.0621 (2)
O1	0.5557 (3)	0.48827 (17)	0.28452 (7)	0.0524 (4)
N1	0.2437 (3)	0.60413 (17)	0.30181 (7)	0.0368 (4)
N2	−0.0659 (3)	0.7099 (2)	0.34152 (9)	0.0546 (5)
C1	0.2246 (4)	0.6814 (2)	0.24558 (9)	0.0463 (5)
H1A	0.2710	0.6240	0.2134	0.056*
H1B	0.3169	0.7626	0.2484	0.056*
C2	−0.0101 (4)	0.7238 (3)	0.23335 (11)	0.0596 (7)
H2A	−0.0206	0.7872	0.1999	0.072*
H2B	−0.0967	0.6428	0.2225	0.072*
C3	−0.1002 (4)	0.7918 (3)	0.28650 (11)	0.0602 (7)
H3A	−0.0317	0.8814	0.2925	0.072*
H3B	−0.2551	0.8069	0.2785	0.072*
C4	0.0911 (3)	0.6272 (2)	0.34402 (9)	0.0398 (5)
C5	0.4093 (3)	0.5144 (2)	0.31655 (9)	0.0374 (5)
C6	0.3828 (3)	0.4527 (2)	0.37687 (9)	0.0373 (5)
C7	0.5269 (4)	0.3603 (2)	0.39918 (9)	0.0421 (5)
H7	0.6382	0.3396	0.3745	0.051*
C8	0.5390 (3)	0.2865 (2)	0.45577 (9)	0.0392 (5)
C9	0.3883 (4)	0.3042 (3)	0.49957 (10)	0.0513 (6)
H9	0.2746	0.3664	0.4923	0.062*
C10	0.4019 (4)	0.2333 (3)	0.55293 (10)	0.0521 (6)
H10	0.2986	0.2470	0.5808	0.063*
C11	0.5701 (4)	0.1424 (2)	0.56408 (9)	0.0443 (5)
C12	0.7249 (4)	0.1199 (2)	0.52314 (9)	0.0464 (5)
H12	0.8388	0.0583	0.5312	0.056*
C13	0.7056 (3)	0.1916 (2)	0.46989 (9)	0.0399 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0500 (3)	0.0536 (4)	0.0407 (3)	0.0148 (3)	0.0116 (2)	0.0127 (3)
Cl1	0.0598 (4)	0.0708 (4)	0.0525 (4)	0.0284 (3)	0.0149 (3)	0.0150 (3)
Cl2	0.0798 (5)	0.0653 (4)	0.0408 (3)	0.0008 (3)	−0.0004 (3)	0.0166 (3)
O1	0.0554 (10)	0.0594 (10)	0.0437 (9)	0.0180 (8)	0.0137 (7)	0.0023 (8)
N1	0.0424 (10)	0.0371 (9)	0.0310 (9)	0.0043 (8)	0.0045 (7)	0.0040 (7)
N2	0.0526 (12)	0.0621 (13)	0.0501 (12)	0.0193 (10)	0.0114 (9)	0.0140 (10)
C1	0.0566 (14)	0.0450 (13)	0.0377 (12)	0.0065 (11)	0.0073 (10)	0.0101 (10)
C2	0.0679 (17)	0.0675 (17)	0.0426 (13)	0.0175 (14)	−0.0022 (12)	0.0132 (12)
C3	0.0603 (16)	0.0649 (17)	0.0556 (15)	0.0247 (13)	0.0054 (12)	0.0191 (13)
C4	0.0430 (12)	0.0403 (12)	0.0365 (11)	0.0037 (9)	0.0052 (9)	0.0066 (9)
C5	0.0440 (12)	0.0346 (11)	0.0334 (11)	0.0024 (9)	0.0015 (9)	−0.0039 (8)
C6	0.0437 (12)	0.0364 (11)	0.0317 (10)	0.0040 (9)	0.0021 (8)	−0.0021 (8)
C7	0.0475 (13)	0.0441 (12)	0.0348 (11)	0.0084 (10)	0.0021 (9)	−0.0022 (9)
C8	0.0440 (12)	0.0407 (12)	0.0325 (11)	0.0068 (10)	−0.0015 (8)	−0.0013 (9)
C9	0.0527 (14)	0.0611 (15)	0.0400 (12)	0.0203 (12)	0.0028 (10)	0.0045 (11)
C10	0.0582 (15)	0.0619 (16)	0.0370 (12)	0.0090 (12)	0.0095 (10)	0.0007 (11)
C11	0.0582 (14)	0.0434 (12)	0.0306 (11)	−0.0022 (11)	−0.0015 (9)	0.0039 (9)
C12	0.0543 (14)	0.0435 (13)	0.0408 (12)	0.0125 (10)	−0.0026 (10)	0.0056 (10)
C13	0.0437 (12)	0.0416 (12)	0.0345 (11)	0.0059 (9)	0.0024 (9)	0.0002 (9)

Geometric parameters (Å, º)

S1—C6	1.757 (2)	C3—H3A	0.9700
S1—C4	1.771 (2)	C3—H3B	0.9700
Cl1—C13	1.746 (2)	C5—C6	1.501 (3)
Cl2—C11	1.744 (2)	C6—C7	1.336 (3)
O1—C5	1.215 (2)	C7—C8	1.458 (3)
N1—C5	1.364 (3)	C7—H7	0.9300
N1—C4	1.395 (3)	C8—C13	1.398 (3)
N1—C1	1.468 (3)	C8—C9	1.405 (3)
N2—C4	1.253 (3)	C9—C10	1.381 (3)
N2—C3	1.474 (3)	C9—H9	0.9300
C1—C2	1.511 (3)	C10—C11	1.370 (3)
C1—H1A	0.9700	C10—H10	0.9300
C1—H1B	0.9700	C11—C12	1.383 (3)
C2—C3	1.501 (3)	C12—C13	1.383 (3)
C2—H2A	0.9700	C12—H12	0.9300
C2—H2B	0.9700
C6—S1—C4	92.16 (10)	O1—C5—C6	125.44 (19)
C5—N1—C4	117.44 (17)	N1—C5—C6	110.60 (17)
C5—N1—C1	123.53 (17)	C7—C6—C5	119.97 (19)
C4—N1—C1	118.96 (17)	C7—C6—S1	130.31 (17)
C4—N2—C3	116.79 (19)	C5—C6—S1	109.72 (14)
N1—C1—C2	108.66 (18)	C6—C7—C8	130.8 (2)
N1—C1—H1A	110.0	C6—C7—H7	114.6
C2—C1—H1A	110.0	C8—C7—H7	114.6
N1—C1—H1B	110.0	C13—C8—C9	115.29 (19)
C2—C1—H1B	110.0	C13—C8—C7	121.14 (19)
H1A—C1—H1B	108.3	C9—C8—C7	123.56 (19)
C3—C2—C1	111.7 (2)	C10—C9—C8	122.9 (2)
C3—C2—H2A	109.3	C10—C9—H9	118.6
C1—C2—H2A	109.3	C8—C9—H9	118.6
C3—C2—H2B	109.3	C11—C10—C9	118.8 (2)
C1—C2—H2B	109.3	C11—C10—H10	120.6
H2A—C2—H2B	107.9	C9—C10—H10	120.6
N2—C3—C2	113.1 (2)	C10—C11—C12	121.5 (2)
N2—C3—H3A	109.0	C10—C11—Cl2	119.62 (17)
C2—C3—H3A	109.0	C12—C11—Cl2	118.84 (17)
N2—C3—H3B	109.0	C11—C12—C13	118.2 (2)
C2—C3—H3B	109.0	C11—C12—H12	120.9
H3A—C3—H3B	107.8	C13—C12—H12	120.9
N2—C4—N1	128.45 (19)	C12—C13—C8	123.25 (19)
N2—C4—S1	121.57 (16)	C12—C13—Cl1	116.43 (16)
N1—C4—S1	109.98 (15)	C8—C13—Cl1	120.31 (16)
O1—C5—N1	123.96 (19)
C5—N1—C1—C2	158.0 (2)	N1—C5—C6—S1	−0.6 (2)
C4—N1—C1—C2	−25.0 (3)	C4—S1—C6—C7	179.3 (2)
N1—C1—C2—C3	49.8 (3)	C4—S1—C6—C5	−1.09 (16)
C4—N2—C3—C2	25.2 (3)	C5—C6—C7—C8	179.7 (2)
C1—C2—C3—N2	−51.7 (3)	S1—C6—C7—C8	−0.7 (4)
C3—N2—C4—N1	1.8 (4)	C6—C7—C8—C13	179.3 (2)
C3—N2—C4—S1	−178.95 (18)	C6—C7—C8—C9	−0.8 (4)
C5—N1—C4—N2	175.8 (2)	C13—C8—C9—C10	−0.1 (4)
C1—N1—C4—N2	−1.4 (4)	C7—C8—C9—C10	179.9 (2)
C5—N1—C4—S1	−3.6 (2)	C8—C9—C10—C11	0.5 (4)
C1—N1—C4—S1	179.28 (16)	C9—C10—C11—C12	−0.3 (4)
C6—S1—C4—N2	−176.9 (2)	C9—C10—C11—Cl2	179.04 (19)
C6—S1—C4—N1	2.52 (16)	C10—C11—C12—C13	−0.3 (4)
C4—N1—C5—O1	−177.9 (2)	Cl2—C11—C12—C13	−179.63 (17)
C1—N1—C5—O1	−0.9 (3)	C11—C12—C13—C8	0.7 (3)
C4—N1—C5—C6	2.7 (3)	C11—C12—C13—Cl1	−178.75 (17)
C1—N1—C5—C6	179.77 (18)	C9—C8—C13—C12	−0.5 (3)
O1—C5—C6—C7	−0.4 (3)	C7—C8—C13—C12	179.5 (2)
N1—C5—C6—C7	179.00 (19)	C9—C8—C13—Cl1	178.93 (17)
O1—C5—C6—S1	−179.99 (19)	C7—C8—C13—Cl1	−1.1 (3)