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

The title compound, C₂₃H₁₈Cl₂N₂O₃S·CH₂Cl₂, was synthesized by heating ethyl 2-mercapto-4-methyl-6-phenyl-1,6-di­hydro­pyrimidine-5-carboxyl­ate, ethyl chloro­acetate and 2,4-di­chloro­benz­aldehyde in ethanol. In the mol­ecule, the nearly planar thia­zole ring is fused with a di­hydro­pyrimidine ring in a boat conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.059
• wR factor = 0.179
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.777     0.933
            Tmin' and Tmax expected:      0.879     0.933
            RR' =      0.884
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C21
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4    ..  S1       =       3.50 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

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.

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

Crystal data

C23H18Cl2N2O3S·CH2Cl2	Z = 2
Mr = 558.28	F(000) = 572
Triclinic, P1	Dx = 1.452 Mg m^−3
Hall symbol: -P 1	Melting point = 182–183 K
a = 9.747 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.291 (4) Å	Cell parameters from 1016 reflections
c = 12.297 (5) Å	θ = 2.2–26.1°
α = 84.546 (7)°	µ = 0.58 mm^−1
β = 74.655 (6)°	T = 293 K
γ = 78.378 (6)°	Block, colorless
V = 1277.1 (9) Å^3	0.22 × 0.16 × 0.12 mm

Data collection

CCD area detector diffractometer	4478 independent reflections
Radiation source: fine-focus sealed tube	2711 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS, Bruker, 1997)	h = −11→11
Tmin = 0.777, Tmax = 0.933	k = −13→8
6583 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.059	w = 1/[σ^2(Fo^2) + (0.0864P)^2 + 0.2487P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.180	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.50 e Å^−3
4478 reflections	Δρmin = −0.46 e Å^−3
309 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	0.31284 (12)	0.21167 (11)	0.97506 (9)	0.0570 (3)
Cl1	0.26079 (15)	−0.29145 (12)	0.96659 (13)	0.0866 (5)
Cl2	−0.21001 (13)	−0.15015 (14)	1.29760 (10)	0.0810 (5)
O1	0.5779 (3)	−0.0232 (3)	0.7739 (2)	0.0559 (8)
O2	0.8771 (5)	0.4473 (4)	0.6447 (3)	0.1065 (15)
O3	0.8904 (3)	0.2702 (3)	0.5744 (2)	0.0573 (8)
N1	0.5409 (3)	0.1799 (3)	0.8048 (2)	0.0414 (8)
N2	0.4691 (4)	0.3797 (3)	0.8725 (3)	0.0546 (9)
C1	0.1000 (5)	0.0240 (4)	1.1163 (4)	0.0613 (12)
H1	0.1219	0.1009	1.1133	0.074*
C2	−0.0227 (5)	−0.0004 (5)	1.1941 (4)	0.0642 (12)
H2	−0.0820	0.0587	1.2420	0.077*
C3	−0.0558 (5)	−0.1150 (5)	1.1996 (4)	0.0569 (12)
C4	0.0317 (5)	−0.2033 (4)	1.1298 (4)	0.0598 (12)
H4	0.0088	−0.2800	1.1345	0.072*
C5	0.1546 (5)	−0.1765 (4)	1.0523 (3)	0.0536 (11)
C6	0.1938 (4)	−0.0611 (4)	1.0411 (3)	0.0455 (10)
C7	0.3213 (4)	−0.0366 (4)	0.9557 (3)	0.0483 (10)
H7	0.3751	−0.1039	0.9160	0.058*
C8	0.3760 (4)	0.0653 (4)	0.9233 (3)	0.0440 (9)
C9	0.5079 (4)	0.0640 (4)	0.8269 (3)	0.0429 (9)
C10	0.4534 (4)	0.2682 (4)	0.8741 (3)	0.0457 (10)
C11	0.5993 (4)	0.4080 (4)	0.7995 (3)	0.0488 (10)
C12	0.6213 (6)	0.5305 (4)	0.8229 (4)	0.0701 (13)
H12A	0.7146	0.5440	0.7791	0.105*
H12B	0.6158	0.5336	0.9018	0.105*
H12C	0.5474	0.5920	0.8029	0.105*
C13	0.6887 (4)	0.3316 (4)	0.7206 (3)	0.0443 (9)
C14	0.6453 (4)	0.2147 (3)	0.7007 (3)	0.0412 (9)
H14	0.7318	0.1510	0.6872	0.049*
C15	0.5798 (4)	0.2250 (3)	0.5999 (3)	0.0421 (9)
C16	0.4818 (5)	0.3279 (4)	0.5802 (4)	0.0558 (11)
H16	0.4591	0.3924	0.6276	0.067*
C17	0.4177 (5)	0.3357 (5)	0.4910 (4)	0.0673 (13)
H17	0.3517	0.4045	0.4791	0.081*
C18	0.4525 (6)	0.2405 (5)	0.4199 (4)	0.0725 (15)
H18	0.4094	0.2454	0.3602	0.087*
C19	0.5490 (6)	0.1398 (5)	0.4365 (4)	0.0709 (14)
H19	0.5723	0.0764	0.3879	0.085*
C20	0.6132 (5)	0.1315 (4)	0.5266 (4)	0.0608 (12)
H20	0.6793	0.0623	0.5375	0.073*
C21	0.8248 (5)	0.3592 (4)	0.6451 (4)	0.0536 (11)
C22	1.0221 (5)	0.2864 (5)	0.4892 (4)	0.0655 (13)
H22A	1.0959	0.2974	0.5250	0.079*
H22B	1.0027	0.3573	0.4406	0.079*
C23	1.0718 (6)	0.1761 (6)	0.4223 (5)	0.0948 (18)
H23A	1.0936	0.1070	0.4709	0.142*
H23B	1.1570	0.1850	0.3638	0.142*
H23C	0.9968	0.1650	0.3891	0.142*
Cl3	0.75820 (17)	0.38100 (16)	0.31070 (14)	0.1007 (5)
Cl4	1.0218 (2)	0.4050 (2)	0.13995 (18)	0.1519 (9)
C24	0.8621 (7)	0.4808 (6)	0.2227 (7)	0.125 (3)
H24A	0.8057	0.5287	0.1743	0.150*
H24B	0.8840	0.5357	0.2691	0.150*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0482 (6)	0.0654 (7)	0.0518 (6)	−0.0183 (5)	0.0041 (5)	−0.0066 (5)
Cl1	0.0782 (9)	0.0739 (9)	0.1017 (10)	−0.0288 (7)	0.0035 (8)	−0.0175 (8)
Cl2	0.0536 (7)	0.1247 (12)	0.0630 (8)	−0.0368 (7)	−0.0073 (6)	0.0268 (7)
O1	0.0542 (18)	0.0500 (18)	0.0578 (18)	−0.0116 (14)	−0.0031 (15)	−0.0015 (15)
O2	0.107 (3)	0.100 (3)	0.108 (3)	−0.073 (3)	0.032 (2)	−0.033 (2)
O3	0.0394 (16)	0.0639 (19)	0.0650 (19)	−0.0183 (14)	−0.0003 (14)	−0.0029 (16)
N1	0.0355 (17)	0.0469 (19)	0.0404 (17)	−0.0113 (14)	−0.0050 (14)	0.0001 (15)
N2	0.051 (2)	0.056 (2)	0.056 (2)	−0.0160 (17)	−0.0030 (17)	−0.0131 (18)
C1	0.061 (3)	0.068 (3)	0.056 (3)	−0.027 (2)	−0.006 (2)	−0.002 (2)
C2	0.055 (3)	0.085 (4)	0.049 (3)	−0.018 (2)	−0.003 (2)	−0.004 (2)
C3	0.042 (2)	0.084 (3)	0.047 (2)	−0.022 (2)	−0.014 (2)	0.017 (2)
C4	0.056 (3)	0.068 (3)	0.064 (3)	−0.031 (2)	−0.020 (2)	0.015 (2)
C5	0.050 (3)	0.066 (3)	0.051 (2)	−0.021 (2)	−0.017 (2)	0.004 (2)
C6	0.041 (2)	0.058 (3)	0.041 (2)	−0.0164 (19)	−0.0150 (18)	0.0065 (19)
C7	0.044 (2)	0.057 (3)	0.046 (2)	−0.0128 (19)	−0.0144 (19)	0.003 (2)
C8	0.040 (2)	0.056 (3)	0.038 (2)	−0.0147 (18)	−0.0106 (18)	0.0018 (18)
C9	0.043 (2)	0.051 (3)	0.038 (2)	−0.0140 (19)	−0.0143 (18)	0.0005 (19)
C10	0.037 (2)	0.059 (3)	0.042 (2)	−0.0110 (19)	−0.0090 (18)	−0.002 (2)
C11	0.049 (2)	0.048 (2)	0.054 (3)	−0.0150 (19)	−0.018 (2)	0.001 (2)
C12	0.072 (3)	0.061 (3)	0.075 (3)	−0.021 (2)	−0.007 (3)	−0.012 (2)
C13	0.045 (2)	0.047 (2)	0.046 (2)	−0.0157 (18)	−0.0145 (19)	0.0017 (19)
C14	0.034 (2)	0.046 (2)	0.044 (2)	−0.0106 (17)	−0.0082 (17)	−0.0018 (18)
C15	0.038 (2)	0.049 (2)	0.040 (2)	−0.0178 (18)	−0.0053 (17)	0.0013 (18)
C16	0.050 (3)	0.063 (3)	0.056 (3)	−0.013 (2)	−0.015 (2)	0.000 (2)
C17	0.056 (3)	0.078 (3)	0.072 (3)	−0.020 (2)	−0.025 (3)	0.021 (3)
C18	0.082 (4)	0.099 (4)	0.057 (3)	−0.053 (3)	−0.034 (3)	0.021 (3)
C19	0.093 (4)	0.073 (3)	0.058 (3)	−0.035 (3)	−0.022 (3)	−0.006 (3)
C20	0.066 (3)	0.062 (3)	0.058 (3)	−0.023 (2)	−0.014 (2)	0.003 (2)
C21	0.047 (2)	0.062 (3)	0.056 (3)	−0.024 (2)	−0.010 (2)	0.002 (2)
C22	0.043 (3)	0.094 (4)	0.056 (3)	−0.027 (2)	0.000 (2)	0.005 (3)
C23	0.062 (4)	0.107 (5)	0.102 (4)	−0.013 (3)	0.008 (3)	−0.031 (4)
Cl3	0.0764 (10)	0.1109 (12)	0.1040 (11)	−0.0235 (8)	−0.0027 (8)	0.0047 (9)
Cl4	0.0777 (12)	0.232 (3)	0.1399 (17)	−0.0523 (14)	0.0141 (11)	−0.0440 (17)
C24	0.073 (4)	0.109 (5)	0.175 (7)	−0.021 (4)	0.004 (4)	−0.006 (5)

Geometric parameters (Å, º)

S1—C8	1.761 (4)	C12—H12A	0.9600
S1—C10	1.769 (4)	C12—H12B	0.9600
Cl1—C5	1.735 (5)	C12—H12C	0.9600
Cl2—C3	1.749 (4)	C13—C21	1.476 (6)
O1—C9	1.215 (4)	C13—C14	1.525 (5)
O2—C21	1.204 (5)	C14—C15	1.522 (5)
O3—C21	1.337 (5)	C14—H14	0.9800
O3—C22	1.458 (5)	C15—C20	1.386 (6)
N1—C10	1.372 (5)	C15—C16	1.394 (6)
N1—C9	1.395 (5)	C16—C17	1.387 (6)
N1—C14	1.484 (4)	C16—H16	0.9300
N2—C10	1.296 (5)	C17—C18	1.381 (7)
N2—C11	1.423 (5)	C17—H17	0.9300
C1—C2	1.378 (6)	C18—C19	1.359 (7)
C1—C6	1.408 (6)	C18—H18	0.9300
C1—H1	0.9300	C19—C20	1.396 (6)
C2—C3	1.387 (7)	C19—H19	0.9300
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.375 (6)	C22—C23	1.484 (7)
C4—C5	1.386 (6)	C22—H22A	0.9700
C4—H4	0.9300	C22—H22B	0.9700
C5—C6	1.415 (6)	C23—H23A	0.9600
C6—C7	1.455 (5)	C23—H23B	0.9600
C7—C8	1.346 (5)	C23—H23C	0.9600
C7—H7	0.9300	Cl3—C24	1.764 (7)
C8—C9	1.499 (5)	Cl4—C24	1.726 (7)
C11—C13	1.361 (5)	C24—H24A	0.9700
C11—C12	1.507 (6)	C24—H24B	0.9700
C8—S1—C10	91.40 (19)	C21—C13—C14	116.3 (3)
C21—O3—C22	118.3 (3)	N1—C14—C15	110.1 (3)
C10—N1—C9	116.4 (3)	N1—C14—C13	108.3 (3)
C10—N1—C14	119.4 (3)	C15—C14—C13	113.2 (3)
C9—N1—C14	123.2 (3)	N1—C14—H14	108.4
C10—N2—C11	115.5 (3)	C15—C14—H14	108.4
C2—C1—C6	123.5 (4)	C13—C14—H14	108.4
C2—C1—H1	118.2	C20—C15—C16	118.1 (4)
C6—C1—H1	118.2	C20—C15—C14	121.1 (4)
C1—C2—C3	118.6 (5)	C16—C15—C14	120.8 (4)
C1—C2—H2	120.7	C17—C16—C15	121.0 (4)
C3—C2—H2	120.7	C17—C16—H16	119.5
C4—C3—C2	121.1 (4)	C15—C16—H16	119.5
C4—C3—Cl2	118.8 (4)	C18—C17—C16	119.5 (5)
C2—C3—Cl2	120.1 (4)	C18—C17—H17	120.2
C3—C4—C5	119.2 (4)	C16—C17—H17	120.2
C3—C4—H4	120.4	C19—C18—C17	120.6 (4)
C5—C4—H4	120.4	C19—C18—H18	119.7
C4—C5—C6	122.7 (4)	C17—C18—H18	119.7
C4—C5—Cl1	117.1 (3)	C18—C19—C20	120.0 (5)
C6—C5—Cl1	120.3 (3)	C18—C19—H19	120.0
C1—C6—C5	114.9 (4)	C20—C19—H19	120.0
C1—C6—C7	124.7 (4)	C15—C20—C19	120.8 (5)
C5—C6—C7	120.4 (4)	C15—C20—H20	119.6
C8—C7—C6	132.0 (4)	C19—C20—H20	119.6
C8—C7—H7	114.0	O2—C21—O3	121.6 (4)
C6—C7—H7	114.0	O2—C21—C13	127.1 (4)
C7—C8—C9	119.9 (4)	O3—C21—C13	111.2 (4)
C7—C8—S1	129.8 (3)	O3—C22—C23	107.4 (4)
C9—C8—S1	110.3 (3)	O3—C22—H22A	110.2
O1—C9—N1	123.5 (4)	C23—C22—H22A	110.2
O1—C9—C8	126.5 (4)	O3—C22—H22B	110.2
N1—C9—C8	110.0 (3)	C23—C22—H22B	110.2
N2—C10—N1	126.7 (4)	H22A—C22—H22B	108.5
N2—C10—S1	121.5 (3)	C22—C23—H23A	109.5
N1—C10—S1	111.8 (3)	C22—C23—H23B	109.5
C13—C11—N2	122.7 (4)	H23A—C23—H23B	109.5
C13—C11—C12	126.5 (4)	C22—C23—H23C	109.5
N2—C11—C12	110.7 (3)	H23A—C23—H23C	109.5
C11—C12—H12A	109.5	H23B—C23—H23C	109.5
C11—C12—H12B	109.5	Cl4—C24—Cl3	112.2 (4)
H12A—C12—H12B	109.5	Cl4—C24—H24A	109.2
C11—C12—H12C	109.5	Cl3—C24—H24A	109.2
H12A—C12—H12C	109.5	Cl4—C24—H24B	109.2
H12B—C12—H12C	109.5	Cl3—C24—H24B	109.2
C11—C13—C21	123.4 (4)	H24A—C24—H24B	107.9
C11—C13—C14	120.2 (4)
C6—C1—C2—C3	0.3 (7)	C8—S1—C10—N1	0.9 (3)
C1—C2—C3—C4	0.5 (7)	C10—N2—C11—C13	12.1 (6)
C1—C2—C3—Cl2	179.7 (3)	C10—N2—C11—C12	−167.6 (4)
C2—C3—C4—C5	−0.4 (7)	N2—C11—C13—C21	−179.3 (4)
Cl2—C3—C4—C5	−179.6 (3)	C12—C11—C13—C21	0.4 (7)
C3—C4—C5—C6	−0.5 (6)	N2—C11—C13—C14	5.2 (6)
C3—C4—C5—Cl1	180.0 (3)	C12—C11—C13—C14	−175.1 (4)
C2—C1—C6—C5	−1.1 (6)	C10—N1—C14—C15	−95.5 (4)
C2—C1—C6—C7	177.9 (4)	C9—N1—C14—C15	72.8 (4)
C4—C5—C6—C1	1.2 (6)	C10—N1—C14—C13	28.8 (4)
Cl1—C5—C6—C1	−179.3 (3)	C9—N1—C14—C13	−162.9 (3)
C4—C5—C6—C7	−177.9 (4)	C11—C13—C14—N1	−24.3 (5)
Cl1—C5—C6—C7	1.6 (5)	C21—C13—C14—N1	160.0 (3)
C1—C6—C7—C8	−3.8 (7)	C11—C13—C14—C15	98.2 (4)
C5—C6—C7—C8	175.2 (4)	C21—C13—C14—C15	−77.6 (4)
C6—C7—C8—C9	−177.0 (4)	N1—C14—C15—C20	−98.9 (4)
C6—C7—C8—S1	0.9 (7)	C13—C14—C15—C20	139.7 (4)
C10—S1—C8—C7	−177.9 (4)	N1—C14—C15—C16	79.7 (4)
C10—S1—C8—C9	0.2 (3)	C13—C14—C15—C16	−41.7 (5)
C10—N1—C9—O1	−178.3 (3)	C20—C15—C16—C17	1.1 (6)
C14—N1—C9—O1	13.0 (6)	C14—C15—C16—C17	−177.5 (4)
C10—N1—C9—C8	1.8 (4)	C15—C16—C17—C18	−0.6 (7)
C14—N1—C9—C8	−166.8 (3)	C16—C17—C18—C19	−0.2 (7)
C7—C8—C9—O1	−2.6 (6)	C17—C18—C19—C20	0.5 (7)
S1—C8—C9—O1	179.1 (3)	C16—C15—C20—C19	−0.8 (6)
C7—C8—C9—N1	177.2 (3)	C14—C15—C20—C19	177.8 (4)
S1—C8—C9—N1	−1.1 (4)	C18—C19—C20—C15	0.0 (7)
C11—N2—C10—N1	−7.4 (6)	C22—O3—C21—O2	−5.1 (6)
C11—N2—C10—S1	170.2 (3)	C22—O3—C21—C13	176.3 (3)
C9—N1—C10—N2	176.1 (4)	C11—C13—C21—O2	2.7 (7)
C14—N1—C10—N2	−14.9 (6)	C14—C13—C21—O2	178.3 (5)
C9—N1—C10—S1	−1.7 (4)	C11—C13—C21—O3	−178.8 (4)
C14—N1—C10—S1	167.3 (2)	C14—C13—C21—O3	−3.1 (5)
C8—S1—C10—N2	−177.1 (3)	C21—O3—C22—C23	−179.7 (4)