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In the title compound, C23H19ClN2O3S, the central pyrimidine ring is significantly puckered, assuming a distorted chair conformation. Inter­molecular C—H...O hydrogen-bond and π–π stacking inter­actions contribute to the stability of the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050379/wn2094sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050379/wn2094Isup2.hkl
Contains datablock I

CCDC reference: 630508

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.065
  • wR factor = 0.145
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.72 Ratio
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 500 Ang. PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.74 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 - C19 .. 5.12 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

(2Z)-Ethyl 2-(4-chlorobenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro- 5H-1,3thiazolo[3,2-a]pyrimidine-6-carboxylate top
Crystal data top
C23H19ClN2O3SF(000) = 912
Mr = 438.91Dx = 1.352 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 9.597 (5) Åθ = 3–25°
b = 10.907 (5) ŵ = 0.30 mm1
c = 20.607 (5) ÅT = 293 K
β = 91.970 (5)°Needle, yellow
V = 2155.8 (16) Å30.4 × 0.2 × 0.1 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
3698 independent reflections
Radiation source: fine-focus sealed tube2615 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ωφ scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1011
Tmin = 0.93, Tmax = 0.978k = 1211
10312 measured reflectionsl = 2423
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0629P)2 + 0.0325P]
where P = (Fo2 + 2Fc2)/3
3698 reflections(Δ/σ)max = 0.002
272 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.20 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.11363 (9)0.31261 (8)0.03140 (4)0.0396 (3)
Cl10.63964 (10)0.73797 (10)0.13959 (5)0.0686 (4)
N10.0806 (3)0.1437 (2)0.01069 (14)0.0451 (8)
N20.0213 (3)0.2811 (2)0.07413 (12)0.0307 (6)
O10.0406 (2)0.4477 (2)0.13617 (11)0.0437 (6)
O20.3076 (3)0.1354 (2)0.18935 (13)0.0581 (7)
O30.3689 (3)0.0200 (3)0.12406 (18)0.0974 (11)
C10.0094 (3)0.2320 (3)0.01363 (15)0.0344 (8)
C20.0973 (3)0.2160 (3)0.12478 (16)0.0372 (8)
H20.15320.27630.14770.045*
C30.1964 (3)0.1252 (3)0.09193 (18)0.0424 (9)
C40.1850 (3)0.0944 (3)0.02916 (19)0.0432 (9)
C50.0498 (3)0.3892 (3)0.08659 (15)0.0291 (7)
C60.1366 (3)0.4214 (3)0.03055 (14)0.0291 (7)
C70.2785 (4)0.0084 (3)0.0087 (2)0.0626 (12)
H7A0.22700.06350.02000.094*
H7B0.31300.04830.04750.094*
H7C0.35550.01470.01720.094*
C80.3006 (4)0.0702 (4)0.1346 (2)0.0557 (11)
C90.3953 (5)0.0911 (4)0.2400 (2)0.0734 (14)
H9A0.35450.01870.26030.088*
H9B0.48700.07010.22210.088*
C100.4055 (6)0.1913 (5)0.2879 (2)0.108 (2)
H10A0.46390.16580.32230.161*
H10B0.44490.26260.26710.161*
H10C0.31420.21050.30560.161*
C110.0039 (3)0.1574 (3)0.17399 (16)0.0404 (9)
C120.0364 (5)0.2141 (4)0.23189 (19)0.0658 (12)
H120.00590.28830.24180.079*
C130.1314 (6)0.1621 (5)0.2758 (2)0.0901 (17)
H130.15240.20110.31500.108*
C140.1940 (5)0.0543 (6)0.2617 (3)0.095 (2)
H140.25920.02020.29080.114*
C150.1611 (5)0.0038 (5)0.2048 (3)0.0845 (16)
H150.20230.07890.19600.101*
C160.0673 (4)0.0471 (4)0.1598 (2)0.0571 (11)
H160.04720.00760.12060.068*
C170.2202 (3)0.5198 (3)0.03420 (16)0.0357 (8)
H170.21490.56380.07270.043*
C180.3181 (3)0.5701 (3)0.01140 (16)0.0356 (8)
C190.3314 (4)0.5309 (3)0.07485 (18)0.0468 (9)
H190.27330.46900.09110.056*
C200.4288 (4)0.5813 (3)0.11438 (18)0.0518 (10)
H200.43680.55340.15670.062*
C210.5143 (4)0.6734 (3)0.0906 (2)0.0486 (10)
C220.5031 (4)0.7156 (3)0.0286 (2)0.0503 (10)
H220.56070.77830.01300.060*
C230.4057 (3)0.6642 (3)0.01034 (18)0.0448 (9)
H230.39810.69310.05250.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0433 (5)0.0396 (5)0.0364 (5)0.0042 (4)0.0091 (4)0.0025 (4)
Cl10.0434 (6)0.0788 (8)0.0847 (8)0.0058 (5)0.0167 (5)0.0393 (6)
N10.0464 (18)0.0401 (17)0.0486 (19)0.0033 (15)0.0015 (15)0.0115 (14)
N20.0312 (15)0.0262 (14)0.0346 (15)0.0040 (12)0.0017 (12)0.0043 (11)
O10.0480 (15)0.0461 (14)0.0376 (14)0.0107 (11)0.0079 (11)0.0079 (11)
O20.0461 (16)0.0670 (18)0.0622 (18)0.0130 (14)0.0153 (13)0.0231 (15)
O30.086 (2)0.082 (2)0.125 (3)0.050 (2)0.026 (2)0.001 (2)
C10.0351 (19)0.0332 (18)0.035 (2)0.0072 (16)0.0001 (15)0.0024 (15)
C20.0337 (19)0.0336 (18)0.044 (2)0.0018 (15)0.0038 (16)0.0100 (15)
C30.0299 (19)0.039 (2)0.058 (2)0.0014 (16)0.0012 (17)0.0107 (18)
C40.0306 (19)0.0317 (19)0.067 (3)0.0009 (16)0.0023 (18)0.0033 (17)
C50.0281 (17)0.0270 (17)0.0317 (19)0.0016 (14)0.0032 (14)0.0049 (14)
C60.0260 (17)0.0286 (17)0.0329 (18)0.0010 (14)0.0026 (14)0.0030 (13)
C70.051 (3)0.051 (2)0.085 (3)0.009 (2)0.005 (2)0.022 (2)
C80.036 (2)0.051 (3)0.080 (3)0.009 (2)0.002 (2)0.019 (2)
C90.062 (3)0.090 (3)0.069 (3)0.018 (3)0.017 (2)0.043 (3)
C100.120 (5)0.155 (5)0.050 (3)0.040 (4)0.022 (3)0.021 (3)
C110.0304 (19)0.049 (2)0.042 (2)0.0079 (17)0.0022 (16)0.0192 (17)
C120.081 (3)0.068 (3)0.048 (3)0.017 (2)0.007 (2)0.018 (2)
C130.098 (4)0.113 (4)0.057 (3)0.036 (4)0.026 (3)0.036 (3)
C140.060 (3)0.127 (5)0.096 (4)0.020 (3)0.026 (3)0.071 (4)
C150.052 (3)0.094 (4)0.108 (4)0.014 (3)0.001 (3)0.051 (3)
C160.042 (2)0.063 (3)0.065 (3)0.005 (2)0.002 (2)0.023 (2)
C170.0347 (19)0.0346 (19)0.038 (2)0.0011 (16)0.0011 (15)0.0011 (15)
C180.0330 (18)0.0321 (18)0.042 (2)0.0009 (15)0.0016 (16)0.0093 (15)
C190.044 (2)0.040 (2)0.057 (3)0.0055 (18)0.0036 (18)0.0112 (18)
C200.046 (2)0.061 (2)0.049 (2)0.004 (2)0.0050 (19)0.0168 (19)
C210.032 (2)0.047 (2)0.068 (3)0.0055 (18)0.0080 (18)0.028 (2)
C220.034 (2)0.041 (2)0.075 (3)0.0105 (18)0.002 (2)0.012 (2)
C230.041 (2)0.038 (2)0.056 (2)0.0042 (17)0.0023 (18)0.0032 (17)
Geometric parameters (Å, º) top
S1—C61.751 (3)C10—H10A0.9600
S1—C11.761 (3)C10—H10B0.9600
Cl1—C211.745 (4)C10—H10C0.9600
N1—C11.274 (4)C11—C121.370 (5)
N1—C41.423 (4)C11—C161.385 (5)
N2—C11.365 (4)C12—C131.384 (6)
N2—C51.382 (4)C12—H120.9300
N2—C21.476 (4)C13—C141.356 (7)
O1—C51.210 (4)C13—H130.9300
O2—C81.337 (5)C14—C151.360 (7)
O2—C91.446 (4)C14—H140.9300
O3—C81.198 (4)C15—C161.386 (5)
C2—C31.516 (4)C15—H150.9300
C2—C111.521 (4)C16—H160.9300
C2—H20.9800C17—C181.458 (4)
C3—C41.345 (5)C17—H170.9300
C3—C81.480 (5)C18—C191.386 (5)
C4—C71.498 (5)C18—C231.391 (4)
C5—C61.488 (4)C19—C201.375 (5)
C6—C171.341 (4)C19—H190.9300
C7—H7A0.9600C20—C211.377 (5)
C7—H7B0.9600C20—H200.9300
C7—H7C0.9600C21—C221.366 (5)
C9—C101.478 (6)C22—C231.373 (5)
C9—H9A0.9700C22—H220.9300
C9—H9B0.9700C23—H230.9300
C6—S1—C191.36 (15)H10A—C10—H10B109.5
C1—N1—C4116.0 (3)C9—C10—H10C109.5
C1—N2—C5116.6 (3)H10A—C10—H10C109.5
C1—N2—C2121.0 (3)H10B—C10—H10C109.5
C5—N2—C2122.2 (3)C12—C11—C16119.2 (3)
C8—O2—C9118.7 (3)C12—C11—C2120.8 (3)
N1—C1—N2126.5 (3)C16—C11—C2120.0 (3)
N1—C1—S1122.0 (3)C11—C12—C13120.6 (5)
N2—C1—S1111.3 (2)C11—C12—H12119.7
N2—C2—C3108.4 (3)C13—C12—H12119.7
N2—C2—C11110.7 (3)C14—C13—C12120.2 (5)
C3—C2—C11113.6 (3)C14—C13—H13119.9
N2—C2—H2108.0C12—C13—H13119.9
C3—C2—H2108.0C13—C14—C15119.8 (5)
C11—C2—H2108.0C13—C14—H14120.1
C4—C3—C8123.3 (3)C15—C14—H14120.1
C4—C3—C2121.5 (3)C14—C15—C16121.1 (5)
C8—C3—C2115.2 (3)C14—C15—H15119.5
C3—C4—N1122.9 (3)C16—C15—H15119.5
C3—C4—C7126.2 (3)C11—C16—C15119.1 (4)
N1—C4—C7110.9 (3)C11—C16—H16120.4
O1—C5—N2123.8 (3)C15—C16—H16120.4
O1—C5—C6126.1 (3)C6—C17—C18131.5 (3)
N2—C5—C6110.0 (3)C6—C17—H17114.2
C17—C6—C5119.7 (3)C18—C17—H17114.2
C17—C6—S1130.0 (3)C19—C18—C23117.2 (3)
C5—C6—S1110.3 (2)C19—C18—C17125.0 (3)
C4—C7—H7A109.5C23—C18—C17117.8 (3)
C4—C7—H7B109.5C20—C19—C18121.5 (3)
H7A—C7—H7B109.5C20—C19—H19119.3
C4—C7—H7C109.5C18—C19—H19119.3
H7A—C7—H7C109.5C19—C20—C21119.3 (4)
H7B—C7—H7C109.5C19—C20—H20120.3
O3—C8—O2123.1 (4)C21—C20—H20120.3
O3—C8—C3127.0 (4)C22—C21—C20120.9 (3)
O2—C8—C3109.9 (3)C22—C21—Cl1118.9 (3)
O2—C9—C10106.8 (4)C20—C21—Cl1120.2 (3)
O2—C9—H9A110.4C21—C22—C23119.1 (3)
C10—C9—H9A110.4C21—C22—H22120.4
O2—C9—H9B110.4C23—C22—H22120.4
C10—C9—H9B110.4C22—C23—C18122.0 (4)
H9A—C9—H9B108.6C22—C23—H23119.0
C9—C10—H10A109.5C18—C23—H23119.0
C9—C10—H10B109.5
C4—N1—C1—N21.8 (5)C9—O2—C8—C3175.0 (3)
C4—N1—C1—S1174.4 (2)C4—C3—C8—O314.1 (6)
C5—N2—C1—N1169.6 (3)C2—C3—C8—O3163.2 (4)
C2—N2—C1—N115.1 (5)C4—C3—C8—O2167.0 (3)
C5—N2—C1—S17.0 (3)C2—C3—C8—O215.6 (4)
C2—N2—C1—S1168.3 (2)C8—O2—C9—C10168.9 (4)
C6—S1—C1—N1171.8 (3)N2—C2—C11—C1298.2 (4)
C6—S1—C1—N24.9 (2)C3—C2—C11—C12139.5 (3)
C1—N2—C2—C321.5 (4)N2—C2—C11—C1680.1 (4)
C5—N2—C2—C3163.5 (3)C3—C2—C11—C1642.2 (4)
C1—N2—C2—C11103.7 (3)C16—C11—C12—C130.0 (6)
C5—N2—C2—C1171.3 (4)C2—C11—C12—C13178.3 (4)
N2—C2—C3—C414.4 (4)C11—C12—C13—C140.3 (7)
C11—C2—C3—C4109.2 (4)C12—C13—C14—C151.3 (8)
N2—C2—C3—C8168.2 (3)C13—C14—C15—C161.9 (8)
C11—C2—C3—C868.3 (4)C12—C11—C16—C150.6 (5)
C8—C3—C4—N1177.1 (3)C2—C11—C16—C15178.9 (3)
C2—C3—C4—N10.1 (5)C14—C15—C16—C111.6 (6)
C8—C3—C4—C74.3 (6)C5—C6—C17—C18177.9 (3)
C2—C3—C4—C7178.5 (3)S1—C6—C17—C180.7 (5)
C1—N1—C4—C39.4 (5)C6—C17—C18—C198.8 (6)
C1—N1—C4—C7169.4 (3)C6—C17—C18—C23170.7 (3)
C1—N2—C5—O1174.3 (3)C23—C18—C19—C201.1 (5)
C2—N2—C5—O110.5 (4)C17—C18—C19—C20178.5 (3)
C1—N2—C5—C65.4 (4)C18—C19—C20—C210.5 (5)
C2—N2—C5—C6169.8 (2)C19—C20—C21—C220.3 (5)
O1—C5—C6—C174.0 (5)C19—C20—C21—Cl1179.4 (3)
N2—C5—C6—C17176.3 (3)C20—C21—C22—C230.5 (5)
O1—C5—C6—S1178.3 (3)Cl1—C21—C22—C23179.3 (3)
N2—C5—C6—S11.4 (3)C21—C22—C23—C180.1 (5)
C1—S1—C6—C17179.3 (3)C19—C18—C23—C220.9 (5)
C1—S1—C6—C51.9 (2)C17—C18—C23—C22178.7 (3)
C9—O2—C8—O33.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···S10.932.633.311 (4)131
C7—H7C···O30.962.212.915 (6)129
C14—H14···O1i0.932.533.450 (5)172
Symmetry code: (i) x+1/2, y1/2, z+1/2.
 

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