Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002740/om6208sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002740/om6208Isup2.hkl
Contains datablock I

CCDC reference: 236066

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 top

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 top
Crystal data top
C23H18Cl2N2O3S·CH2Cl2Z = 2
Mr = 558.28F(000) = 572
Triclinic, P1Dx = 1.452 Mg m3
Hall symbol: -P 1Melting point = 182–183 K
a = 9.747 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.291 (4) ÅCell parameters from 1016 reflections
c = 12.297 (5) Åθ = 2.2–26.1°
α = 84.546 (7)°µ = 0.58 mm1
β = 74.655 (6)°T = 293 K
γ = 78.378 (6)°Block, colorless
V = 1277.1 (9) Å30.22 × 0.16 × 0.12 mm
Data collection top
CCD area detector
diffractometer
4478 independent reflections
Radiation source: fine-focus sealed tube2711 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS, Bruker, 1997)
h = 1111
Tmin = 0.777, Tmax = 0.933k = 138
6583 measured reflectionsl = 1414
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059 w = 1/[σ2(Fo2) + (0.0864P)2 + 0.2487P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.180(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.50 e Å3
4478 reflectionsΔρmin = 0.46 e Å3
309 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.31284 (12)0.21167 (11)0.97506 (9)0.0570 (3)
Cl10.26079 (15)0.29145 (12)0.96659 (13)0.0866 (5)
Cl20.21001 (13)0.15015 (14)1.29760 (10)0.0810 (5)
O10.5779 (3)0.0232 (3)0.7739 (2)0.0559 (8)
O20.8771 (5)0.4473 (4)0.6447 (3)0.1065 (15)
O30.8904 (3)0.2702 (3)0.5744 (2)0.0573 (8)
N10.5409 (3)0.1799 (3)0.8048 (2)0.0414 (8)
N20.4691 (4)0.3797 (3)0.8725 (3)0.0546 (9)
C10.1000 (5)0.0240 (4)1.1163 (4)0.0613 (12)
H10.12190.10091.11330.074*
C20.0227 (5)0.0004 (5)1.1941 (4)0.0642 (12)
H20.08200.05871.24200.077*
C30.0558 (5)0.1150 (5)1.1996 (4)0.0569 (12)
C40.0317 (5)0.2033 (4)1.1298 (4)0.0598 (12)
H40.00880.28001.13450.072*
C50.1546 (5)0.1765 (4)1.0523 (3)0.0536 (11)
C60.1938 (4)0.0611 (4)1.0411 (3)0.0455 (10)
C70.3213 (4)0.0366 (4)0.9557 (3)0.0483 (10)
H70.37510.10390.91600.058*
C80.3760 (4)0.0653 (4)0.9233 (3)0.0440 (9)
C90.5079 (4)0.0640 (4)0.8269 (3)0.0429 (9)
C100.4534 (4)0.2682 (4)0.8741 (3)0.0457 (10)
C110.5993 (4)0.4080 (4)0.7995 (3)0.0488 (10)
C120.6213 (6)0.5305 (4)0.8229 (4)0.0701 (13)
H12A0.71460.54400.77910.105*
H12B0.61580.53360.90180.105*
H12C0.54740.59200.80290.105*
C130.6887 (4)0.3316 (4)0.7206 (3)0.0443 (9)
C140.6453 (4)0.2147 (3)0.7007 (3)0.0412 (9)
H140.73180.15100.68720.049*
C150.5798 (4)0.2250 (3)0.5999 (3)0.0421 (9)
C160.4818 (5)0.3279 (4)0.5802 (4)0.0558 (11)
H160.45910.39240.62760.067*
C170.4177 (5)0.3357 (5)0.4910 (4)0.0673 (13)
H170.35170.40450.47910.081*
C180.4525 (6)0.2405 (5)0.4199 (4)0.0725 (15)
H180.40940.24540.36020.087*
C190.5490 (6)0.1398 (5)0.4365 (4)0.0709 (14)
H190.57230.07640.38790.085*
C200.6132 (5)0.1315 (4)0.5266 (4)0.0608 (12)
H200.67930.06230.53750.073*
C210.8248 (5)0.3592 (4)0.6451 (4)0.0536 (11)
C221.0221 (5)0.2864 (5)0.4892 (4)0.0655 (13)
H22A1.09590.29740.52500.079*
H22B1.00270.35730.44060.079*
C231.0718 (6)0.1761 (6)0.4223 (5)0.0948 (18)
H23A1.09360.10700.47090.142*
H23B1.15700.18500.36380.142*
H23C0.99680.16500.38910.142*
Cl30.75820 (17)0.38100 (16)0.31070 (14)0.1007 (5)
Cl41.0218 (2)0.4050 (2)0.13995 (18)0.1519 (9)
C240.8621 (7)0.4808 (6)0.2227 (7)0.125 (3)
H24A0.80570.52870.17430.150*
H24B0.88400.53570.26910.150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0482 (6)0.0654 (7)0.0518 (6)0.0183 (5)0.0041 (5)0.0066 (5)
Cl10.0782 (9)0.0739 (9)0.1017 (10)0.0288 (7)0.0035 (8)0.0175 (8)
Cl20.0536 (7)0.1247 (12)0.0630 (8)0.0368 (7)0.0073 (6)0.0268 (7)
O10.0542 (18)0.0500 (18)0.0578 (18)0.0116 (14)0.0031 (15)0.0015 (15)
O20.107 (3)0.100 (3)0.108 (3)0.073 (3)0.032 (2)0.033 (2)
O30.0394 (16)0.0639 (19)0.0650 (19)0.0183 (14)0.0003 (14)0.0029 (16)
N10.0355 (17)0.0469 (19)0.0404 (17)0.0113 (14)0.0050 (14)0.0001 (15)
N20.051 (2)0.056 (2)0.056 (2)0.0160 (17)0.0030 (17)0.0131 (18)
C10.061 (3)0.068 (3)0.056 (3)0.027 (2)0.006 (2)0.002 (2)
C20.055 (3)0.085 (4)0.049 (3)0.018 (2)0.003 (2)0.004 (2)
C30.042 (2)0.084 (3)0.047 (2)0.022 (2)0.014 (2)0.017 (2)
C40.056 (3)0.068 (3)0.064 (3)0.031 (2)0.020 (2)0.015 (2)
C50.050 (3)0.066 (3)0.051 (2)0.021 (2)0.017 (2)0.004 (2)
C60.041 (2)0.058 (3)0.041 (2)0.0164 (19)0.0150 (18)0.0065 (19)
C70.044 (2)0.057 (3)0.046 (2)0.0128 (19)0.0144 (19)0.003 (2)
C80.040 (2)0.056 (3)0.038 (2)0.0147 (18)0.0106 (18)0.0018 (18)
C90.043 (2)0.051 (3)0.038 (2)0.0140 (19)0.0143 (18)0.0005 (19)
C100.037 (2)0.059 (3)0.042 (2)0.0110 (19)0.0090 (18)0.002 (2)
C110.049 (2)0.048 (2)0.054 (3)0.0150 (19)0.018 (2)0.001 (2)
C120.072 (3)0.061 (3)0.075 (3)0.021 (2)0.007 (3)0.012 (2)
C130.045 (2)0.047 (2)0.046 (2)0.0157 (18)0.0145 (19)0.0017 (19)
C140.034 (2)0.046 (2)0.044 (2)0.0106 (17)0.0082 (17)0.0018 (18)
C150.038 (2)0.049 (2)0.040 (2)0.0178 (18)0.0053 (17)0.0013 (18)
C160.050 (3)0.063 (3)0.056 (3)0.013 (2)0.015 (2)0.000 (2)
C170.056 (3)0.078 (3)0.072 (3)0.020 (2)0.025 (3)0.021 (3)
C180.082 (4)0.099 (4)0.057 (3)0.053 (3)0.034 (3)0.021 (3)
C190.093 (4)0.073 (3)0.058 (3)0.035 (3)0.022 (3)0.006 (3)
C200.066 (3)0.062 (3)0.058 (3)0.023 (2)0.014 (2)0.003 (2)
C210.047 (2)0.062 (3)0.056 (3)0.024 (2)0.010 (2)0.002 (2)
C220.043 (3)0.094 (4)0.056 (3)0.027 (2)0.000 (2)0.005 (3)
C230.062 (4)0.107 (5)0.102 (4)0.013 (3)0.008 (3)0.031 (4)
Cl30.0764 (10)0.1109 (12)0.1040 (11)0.0235 (8)0.0027 (8)0.0047 (9)
Cl40.0777 (12)0.232 (3)0.1399 (17)0.0523 (14)0.0141 (11)0.0440 (17)
C240.073 (4)0.109 (5)0.175 (7)0.021 (4)0.004 (4)0.006 (5)
Geometric parameters (Å, º) top
S1—C81.761 (4)C12—H12A0.9600
S1—C101.769 (4)C12—H12B0.9600
Cl1—C51.735 (5)C12—H12C0.9600
Cl2—C31.749 (4)C13—C211.476 (6)
O1—C91.215 (4)C13—C141.525 (5)
O2—C211.204 (5)C14—C151.522 (5)
O3—C211.337 (5)C14—H140.9800
O3—C221.458 (5)C15—C201.386 (6)
N1—C101.372 (5)C15—C161.394 (6)
N1—C91.395 (5)C16—C171.387 (6)
N1—C141.484 (4)C16—H160.9300
N2—C101.296 (5)C17—C181.381 (7)
N2—C111.423 (5)C17—H170.9300
C1—C21.378 (6)C18—C191.359 (7)
C1—C61.408 (6)C18—H180.9300
C1—H10.9300C19—C201.396 (6)
C2—C31.387 (7)C19—H190.9300
C2—H20.9300C20—H200.9300
C3—C41.375 (6)C22—C231.484 (7)
C4—C51.386 (6)C22—H22A0.9700
C4—H40.9300C22—H22B0.9700
C5—C61.415 (6)C23—H23A0.9600
C6—C71.455 (5)C23—H23B0.9600
C7—C81.346 (5)C23—H23C0.9600
C7—H70.9300Cl3—C241.764 (7)
C8—C91.499 (5)Cl4—C241.726 (7)
C11—C131.361 (5)C24—H24A0.9700
C11—C121.507 (6)C24—H24B0.9700
C8—S1—C1091.40 (19)C21—C13—C14116.3 (3)
C21—O3—C22118.3 (3)N1—C14—C15110.1 (3)
C10—N1—C9116.4 (3)N1—C14—C13108.3 (3)
C10—N1—C14119.4 (3)C15—C14—C13113.2 (3)
C9—N1—C14123.2 (3)N1—C14—H14108.4
C10—N2—C11115.5 (3)C15—C14—H14108.4
C2—C1—C6123.5 (4)C13—C14—H14108.4
C2—C1—H1118.2C20—C15—C16118.1 (4)
C6—C1—H1118.2C20—C15—C14121.1 (4)
C1—C2—C3118.6 (5)C16—C15—C14120.8 (4)
C1—C2—H2120.7C17—C16—C15121.0 (4)
C3—C2—H2120.7C17—C16—H16119.5
C4—C3—C2121.1 (4)C15—C16—H16119.5
C4—C3—Cl2118.8 (4)C18—C17—C16119.5 (5)
C2—C3—Cl2120.1 (4)C18—C17—H17120.2
C3—C4—C5119.2 (4)C16—C17—H17120.2
C3—C4—H4120.4C19—C18—C17120.6 (4)
C5—C4—H4120.4C19—C18—H18119.7
C4—C5—C6122.7 (4)C17—C18—H18119.7
C4—C5—Cl1117.1 (3)C18—C19—C20120.0 (5)
C6—C5—Cl1120.3 (3)C18—C19—H19120.0
C1—C6—C5114.9 (4)C20—C19—H19120.0
C1—C6—C7124.7 (4)C15—C20—C19120.8 (5)
C5—C6—C7120.4 (4)C15—C20—H20119.6
C8—C7—C6132.0 (4)C19—C20—H20119.6
C8—C7—H7114.0O2—C21—O3121.6 (4)
C6—C7—H7114.0O2—C21—C13127.1 (4)
C7—C8—C9119.9 (4)O3—C21—C13111.2 (4)
C7—C8—S1129.8 (3)O3—C22—C23107.4 (4)
C9—C8—S1110.3 (3)O3—C22—H22A110.2
O1—C9—N1123.5 (4)C23—C22—H22A110.2
O1—C9—C8126.5 (4)O3—C22—H22B110.2
N1—C9—C8110.0 (3)C23—C22—H22B110.2
N2—C10—N1126.7 (4)H22A—C22—H22B108.5
N2—C10—S1121.5 (3)C22—C23—H23A109.5
N1—C10—S1111.8 (3)C22—C23—H23B109.5
C13—C11—N2122.7 (4)H23A—C23—H23B109.5
C13—C11—C12126.5 (4)C22—C23—H23C109.5
N2—C11—C12110.7 (3)H23A—C23—H23C109.5
C11—C12—H12A109.5H23B—C23—H23C109.5
C11—C12—H12B109.5Cl4—C24—Cl3112.2 (4)
H12A—C12—H12B109.5Cl4—C24—H24A109.2
C11—C12—H12C109.5Cl3—C24—H24A109.2
H12A—C12—H12C109.5Cl4—C24—H24B109.2
H12B—C12—H12C109.5Cl3—C24—H24B109.2
C11—C13—C21123.4 (4)H24A—C24—H24B107.9
C11—C13—C14120.2 (4)
C6—C1—C2—C30.3 (7)C8—S1—C10—N10.9 (3)
C1—C2—C3—C40.5 (7)C10—N2—C11—C1312.1 (6)
C1—C2—C3—Cl2179.7 (3)C10—N2—C11—C12167.6 (4)
C2—C3—C4—C50.4 (7)N2—C11—C13—C21179.3 (4)
Cl2—C3—C4—C5179.6 (3)C12—C11—C13—C210.4 (7)
C3—C4—C5—C60.5 (6)N2—C11—C13—C145.2 (6)
C3—C4—C5—Cl1180.0 (3)C12—C11—C13—C14175.1 (4)
C2—C1—C6—C51.1 (6)C10—N1—C14—C1595.5 (4)
C2—C1—C6—C7177.9 (4)C9—N1—C14—C1572.8 (4)
C4—C5—C6—C11.2 (6)C10—N1—C14—C1328.8 (4)
Cl1—C5—C6—C1179.3 (3)C9—N1—C14—C13162.9 (3)
C4—C5—C6—C7177.9 (4)C11—C13—C14—N124.3 (5)
Cl1—C5—C6—C71.6 (5)C21—C13—C14—N1160.0 (3)
C1—C6—C7—C83.8 (7)C11—C13—C14—C1598.2 (4)
C5—C6—C7—C8175.2 (4)C21—C13—C14—C1577.6 (4)
C6—C7—C8—C9177.0 (4)N1—C14—C15—C2098.9 (4)
C6—C7—C8—S10.9 (7)C13—C14—C15—C20139.7 (4)
C10—S1—C8—C7177.9 (4)N1—C14—C15—C1679.7 (4)
C10—S1—C8—C90.2 (3)C13—C14—C15—C1641.7 (5)
C10—N1—C9—O1178.3 (3)C20—C15—C16—C171.1 (6)
C14—N1—C9—O113.0 (6)C14—C15—C16—C17177.5 (4)
C10—N1—C9—C81.8 (4)C15—C16—C17—C180.6 (7)
C14—N1—C9—C8166.8 (3)C16—C17—C18—C190.2 (7)
C7—C8—C9—O12.6 (6)C17—C18—C19—C200.5 (7)
S1—C8—C9—O1179.1 (3)C16—C15—C20—C190.8 (6)
C7—C8—C9—N1177.2 (3)C14—C15—C20—C19177.8 (4)
S1—C8—C9—N11.1 (4)C18—C19—C20—C150.0 (7)
C11—N2—C10—N17.4 (6)C22—O3—C21—O25.1 (6)
C11—N2—C10—S1170.2 (3)C22—O3—C21—C13176.3 (3)
C9—N1—C10—N2176.1 (4)C11—C13—C21—O22.7 (7)
C14—N1—C10—N214.9 (6)C14—C13—C21—O2178.3 (5)
C9—N1—C10—S11.7 (4)C11—C13—C21—O3178.8 (4)
C14—N1—C10—S1167.3 (2)C14—C13—C21—O33.1 (5)
C8—S1—C10—N2177.1 (3)C21—O3—C22—C23179.7 (4)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds