(2Z)-Ethyl 2-(4-chloro­benzyl­idene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

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.

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

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

Crystal data

C23H19ClN2O3S	F(000) = 912
Mr = 438.91	Dx = 1.352 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.597 (5) Å	θ = 3–25°
b = 10.907 (5) Å	µ = 0.30 mm^−1
c = 20.607 (5) Å	T = 293 K
β = 91.970 (5)°	Needle, yellow
V = 2155.8 (16) Å^3	0.4 × 0.2 × 0.1 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	3698 independent reflections
Radiation source: fine-focus sealed tube	2615 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω–φ scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→11
Tmin = 0.93, Tmax = 0.978	k = −12→11
10312 measured reflections	l = −24→23

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0629P)^2 + 0.0325P] where P = (Fo^2 + 2Fc^2)/3
3698 reflections	(Δ/σ)max = 0.002
272 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.11363 (9)	0.31261 (8)	−0.03140 (4)	0.0396 (3)
Cl1	0.63964 (10)	0.73797 (10)	−0.13959 (5)	0.0686 (4)
N1	−0.0806 (3)	0.1437 (2)	−0.01069 (14)	0.0451 (8)
N2	−0.0213 (3)	0.2811 (2)	0.07413 (12)	0.0307 (6)
O1	0.0406 (2)	0.4477 (2)	0.13617 (11)	0.0437 (6)
O2	−0.3076 (3)	0.1354 (2)	0.18935 (13)	0.0581 (7)
O3	−0.3689 (3)	−0.0200 (3)	0.12406 (18)	0.0974 (11)
C1	−0.0094 (3)	0.2320 (3)	0.01363 (15)	0.0344 (8)
C2	−0.0973 (3)	0.2160 (3)	0.12478 (16)	0.0372 (8)
H2	−0.1532	0.2763	0.1477	0.045*
C3	−0.1964 (3)	0.1252 (3)	0.09193 (18)	0.0424 (9)
C4	−0.1850 (3)	0.0944 (3)	0.02916 (19)	0.0432 (9)
C5	0.0498 (3)	0.3892 (3)	0.08659 (15)	0.0291 (7)
C6	0.1366 (3)	0.4214 (3)	0.03055 (14)	0.0291 (7)
C7	−0.2785 (4)	0.0084 (3)	−0.0087 (2)	0.0626 (12)
H7A	−0.2270	−0.0635	−0.0200	0.094*
H7B	−0.3130	0.0483	−0.0475	0.094*
H7C	−0.3555	−0.0147	0.0172	0.094*
C8	−0.3006 (4)	0.0702 (4)	0.1346 (2)	0.0557 (11)
C9	−0.3953 (5)	0.0911 (4)	0.2400 (2)	0.0734 (14)
H9A	−0.3545	0.0187	0.2603	0.088*
H9B	−0.4870	0.0701	0.2221	0.088*
C10	−0.4055 (6)	0.1913 (5)	0.2879 (2)	0.108 (2)
H10A	−0.4639	0.1658	0.3223	0.161*
H10B	−0.4449	0.2626	0.2671	0.161*
H10C	−0.3142	0.2105	0.3056	0.161*
C11	0.0039 (3)	0.1574 (3)	0.17399 (16)	0.0404 (9)
C12	0.0364 (5)	0.2141 (4)	0.23189 (19)	0.0658 (12)
H12	−0.0059	0.2883	0.2418	0.079*
C13	0.1314 (6)	0.1621 (5)	0.2758 (2)	0.0901 (17)
H13	0.1524	0.2011	0.3150	0.108*
C14	0.1940 (5)	0.0543 (6)	0.2617 (3)	0.095 (2)
H14	0.2592	0.0202	0.2908	0.114*
C15	0.1611 (5)	−0.0038 (5)	0.2048 (3)	0.0845 (16)
H15	0.2023	−0.0789	0.1960	0.101*
C16	0.0673 (4)	0.0471 (4)	0.1598 (2)	0.0571 (11)
H16	0.0472	0.0076	0.1206	0.068*
C17	0.2202 (3)	0.5198 (3)	0.03420 (16)	0.0357 (8)
H17	0.2149	0.5638	0.0727	0.043*
C18	0.3181 (3)	0.5701 (3)	−0.01140 (16)	0.0356 (8)
C19	0.3314 (4)	0.5309 (3)	−0.07485 (18)	0.0468 (9)
H19	0.2733	0.4690	−0.0911	0.056*
C20	0.4288 (4)	0.5813 (3)	−0.11438 (18)	0.0518 (10)
H20	0.4368	0.5534	−0.1567	0.062*
C21	0.5143 (4)	0.6734 (3)	−0.0906 (2)	0.0486 (10)
C22	0.5031 (4)	0.7156 (3)	−0.0286 (2)	0.0503 (10)
H22	0.5607	0.7783	−0.0130	0.060*
C23	0.4057 (3)	0.6642 (3)	0.01034 (18)	0.0448 (9)
H23	0.3981	0.6931	0.0525	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0433 (5)	0.0396 (5)	0.0364 (5)	−0.0042 (4)	0.0091 (4)	−0.0025 (4)
Cl1	0.0434 (6)	0.0788 (8)	0.0847 (8)	−0.0058 (5)	0.0167 (5)	0.0393 (6)
N1	0.0464 (18)	0.0401 (17)	0.0486 (19)	−0.0033 (15)	−0.0015 (15)	−0.0115 (14)
N2	0.0312 (15)	0.0262 (14)	0.0346 (15)	−0.0040 (12)	0.0017 (12)	0.0043 (11)
O1	0.0480 (15)	0.0461 (14)	0.0376 (14)	−0.0107 (11)	0.0079 (11)	−0.0079 (11)
O2	0.0461 (16)	0.0670 (18)	0.0622 (18)	−0.0130 (14)	0.0153 (13)	0.0231 (15)
O3	0.086 (2)	0.082 (2)	0.125 (3)	−0.050 (2)	0.026 (2)	0.001 (2)
C1	0.0351 (19)	0.0332 (18)	0.035 (2)	0.0072 (16)	−0.0001 (15)	−0.0024 (15)
C2	0.0337 (19)	0.0336 (18)	0.044 (2)	−0.0018 (15)	0.0038 (16)	0.0100 (15)
C3	0.0299 (19)	0.039 (2)	0.058 (2)	−0.0014 (16)	−0.0012 (17)	0.0107 (18)
C4	0.0306 (19)	0.0317 (19)	0.067 (3)	−0.0009 (16)	0.0023 (18)	0.0033 (17)
C5	0.0281 (17)	0.0270 (17)	0.0317 (19)	−0.0016 (14)	−0.0032 (14)	0.0049 (14)
C6	0.0260 (17)	0.0286 (17)	0.0329 (18)	0.0010 (14)	0.0026 (14)	0.0030 (13)
C7	0.051 (3)	0.051 (2)	0.085 (3)	−0.009 (2)	−0.005 (2)	−0.022 (2)
C8	0.036 (2)	0.051 (3)	0.080 (3)	−0.009 (2)	0.002 (2)	0.019 (2)
C9	0.062 (3)	0.090 (3)	0.069 (3)	−0.018 (3)	0.017 (2)	0.043 (3)
C10	0.120 (5)	0.155 (5)	0.050 (3)	−0.040 (4)	0.022 (3)	0.021 (3)
C11	0.0304 (19)	0.049 (2)	0.042 (2)	−0.0079 (17)	0.0022 (16)	0.0192 (17)
C12	0.081 (3)	0.068 (3)	0.048 (3)	−0.017 (2)	−0.007 (2)	0.018 (2)
C13	0.098 (4)	0.113 (4)	0.057 (3)	−0.036 (4)	−0.026 (3)	0.036 (3)
C14	0.060 (3)	0.127 (5)	0.096 (4)	−0.020 (3)	−0.026 (3)	0.071 (4)
C15	0.052 (3)	0.094 (4)	0.108 (4)	0.014 (3)	−0.001 (3)	0.051 (3)
C16	0.042 (2)	0.063 (3)	0.065 (3)	0.005 (2)	−0.002 (2)	0.023 (2)
C17	0.0347 (19)	0.0346 (19)	0.038 (2)	0.0011 (16)	−0.0011 (15)	0.0011 (15)
C18	0.0330 (18)	0.0321 (18)	0.042 (2)	−0.0009 (15)	0.0016 (16)	0.0093 (15)
C19	0.044 (2)	0.040 (2)	0.057 (3)	−0.0055 (18)	0.0036 (18)	0.0112 (18)
C20	0.046 (2)	0.061 (2)	0.049 (2)	−0.004 (2)	0.0050 (19)	0.0168 (19)
C21	0.032 (2)	0.047 (2)	0.068 (3)	0.0055 (18)	0.0080 (18)	0.028 (2)
C22	0.034 (2)	0.041 (2)	0.075 (3)	−0.0105 (18)	−0.002 (2)	0.012 (2)
C23	0.041 (2)	0.038 (2)	0.056 (2)	−0.0042 (17)	0.0023 (18)	0.0032 (17)

Geometric parameters (Å, º)

S1—C6	1.751 (3)	C10—H10A	0.9600
S1—C1	1.761 (3)	C10—H10B	0.9600
Cl1—C21	1.745 (4)	C10—H10C	0.9600
N1—C1	1.274 (4)	C11—C12	1.370 (5)
N1—C4	1.423 (4)	C11—C16	1.385 (5)
N2—C1	1.365 (4)	C12—C13	1.384 (6)
N2—C5	1.382 (4)	C12—H12	0.9300
N2—C2	1.476 (4)	C13—C14	1.356 (7)
O1—C5	1.210 (4)	C13—H13	0.9300
O2—C8	1.337 (5)	C14—C15	1.360 (7)
O2—C9	1.446 (4)	C14—H14	0.9300
O3—C8	1.198 (4)	C15—C16	1.386 (5)
C2—C3	1.516 (4)	C15—H15	0.9300
C2—C11	1.521 (4)	C16—H16	0.9300
C2—H2	0.9800	C17—C18	1.458 (4)
C3—C4	1.345 (5)	C17—H17	0.9300
C3—C8	1.480 (5)	C18—C19	1.386 (5)
C4—C7	1.498 (5)	C18—C23	1.391 (4)
C5—C6	1.488 (4)	C19—C20	1.375 (5)
C6—C17	1.341 (4)	C19—H19	0.9300
C7—H7A	0.9600	C20—C21	1.377 (5)
C7—H7B	0.9600	C20—H20	0.9300
C7—H7C	0.9600	C21—C22	1.366 (5)
C9—C10	1.478 (6)	C22—C23	1.373 (5)
C9—H9A	0.9700	C22—H22	0.9300
C9—H9B	0.9700	C23—H23	0.9300
C6—S1—C1	91.36 (15)	H10A—C10—H10B	109.5
C1—N1—C4	116.0 (3)	C9—C10—H10C	109.5
C1—N2—C5	116.6 (3)	H10A—C10—H10C	109.5
C1—N2—C2	121.0 (3)	H10B—C10—H10C	109.5
C5—N2—C2	122.2 (3)	C12—C11—C16	119.2 (3)
C8—O2—C9	118.7 (3)	C12—C11—C2	120.8 (3)
N1—C1—N2	126.5 (3)	C16—C11—C2	120.0 (3)
N1—C1—S1	122.0 (3)	C11—C12—C13	120.6 (5)
N2—C1—S1	111.3 (2)	C11—C12—H12	119.7
N2—C2—C3	108.4 (3)	C13—C12—H12	119.7
N2—C2—C11	110.7 (3)	C14—C13—C12	120.2 (5)
C3—C2—C11	113.6 (3)	C14—C13—H13	119.9
N2—C2—H2	108.0	C12—C13—H13	119.9
C3—C2—H2	108.0	C13—C14—C15	119.8 (5)
C11—C2—H2	108.0	C13—C14—H14	120.1
C4—C3—C8	123.3 (3)	C15—C14—H14	120.1
C4—C3—C2	121.5 (3)	C14—C15—C16	121.1 (5)
C8—C3—C2	115.2 (3)	C14—C15—H15	119.5
C3—C4—N1	122.9 (3)	C16—C15—H15	119.5
C3—C4—C7	126.2 (3)	C11—C16—C15	119.1 (4)
N1—C4—C7	110.9 (3)	C11—C16—H16	120.4
O1—C5—N2	123.8 (3)	C15—C16—H16	120.4
O1—C5—C6	126.1 (3)	C6—C17—C18	131.5 (3)
N2—C5—C6	110.0 (3)	C6—C17—H17	114.2
C17—C6—C5	119.7 (3)	C18—C17—H17	114.2
C17—C6—S1	130.0 (3)	C19—C18—C23	117.2 (3)
C5—C6—S1	110.3 (2)	C19—C18—C17	125.0 (3)
C4—C7—H7A	109.5	C23—C18—C17	117.8 (3)
C4—C7—H7B	109.5	C20—C19—C18	121.5 (3)
H7A—C7—H7B	109.5	C20—C19—H19	119.3
C4—C7—H7C	109.5	C18—C19—H19	119.3
H7A—C7—H7C	109.5	C19—C20—C21	119.3 (4)
H7B—C7—H7C	109.5	C19—C20—H20	120.3
O3—C8—O2	123.1 (4)	C21—C20—H20	120.3
O3—C8—C3	127.0 (4)	C22—C21—C20	120.9 (3)
O2—C8—C3	109.9 (3)	C22—C21—Cl1	118.9 (3)
O2—C9—C10	106.8 (4)	C20—C21—Cl1	120.2 (3)
O2—C9—H9A	110.4	C21—C22—C23	119.1 (3)
C10—C9—H9A	110.4	C21—C22—H22	120.4
O2—C9—H9B	110.4	C23—C22—H22	120.4
C10—C9—H9B	110.4	C22—C23—C18	122.0 (4)
H9A—C9—H9B	108.6	C22—C23—H23	119.0
C9—C10—H10A	109.5	C18—C23—H23	119.0
C9—C10—H10B	109.5
C4—N1—C1—N2	1.8 (5)	C9—O2—C8—C3	−175.0 (3)
C4—N1—C1—S1	−174.4 (2)	C4—C3—C8—O3	14.1 (6)
C5—N2—C1—N1	−169.6 (3)	C2—C3—C8—O3	−163.2 (4)
C2—N2—C1—N1	15.1 (5)	C4—C3—C8—O2	−167.0 (3)
C5—N2—C1—S1	7.0 (3)	C2—C3—C8—O2	15.6 (4)
C2—N2—C1—S1	−168.3 (2)	C8—O2—C9—C10	−168.9 (4)
C6—S1—C1—N1	171.8 (3)	N2—C2—C11—C12	98.2 (4)
C6—S1—C1—N2	−4.9 (2)	C3—C2—C11—C12	−139.5 (3)
C1—N2—C2—C3	−21.5 (4)	N2—C2—C11—C16	−80.1 (4)
C5—N2—C2—C3	163.5 (3)	C3—C2—C11—C16	42.2 (4)
C1—N2—C2—C11	103.7 (3)	C16—C11—C12—C13	0.0 (6)
C5—N2—C2—C11	−71.3 (4)	C2—C11—C12—C13	−178.3 (4)
N2—C2—C3—C4	14.4 (4)	C11—C12—C13—C14	0.3 (7)
C11—C2—C3—C4	−109.2 (4)	C12—C13—C14—C15	−1.3 (8)
N2—C2—C3—C8	−168.2 (3)	C13—C14—C15—C16	1.9 (8)
C11—C2—C3—C8	68.3 (4)	C12—C11—C16—C15	0.6 (5)
C8—C3—C4—N1	−177.1 (3)	C2—C11—C16—C15	178.9 (3)
C2—C3—C4—N1	0.1 (5)	C14—C15—C16—C11	−1.6 (6)
C8—C3—C4—C7	4.3 (6)	C5—C6—C17—C18	177.9 (3)
C2—C3—C4—C7	−178.5 (3)	S1—C6—C17—C18	0.7 (5)
C1—N1—C4—C3	−9.4 (5)	C6—C17—C18—C19	8.8 (6)
C1—N1—C4—C7	169.4 (3)	C6—C17—C18—C23	−170.7 (3)
C1—N2—C5—O1	174.3 (3)	C23—C18—C19—C20	1.1 (5)
C2—N2—C5—O1	−10.5 (4)	C17—C18—C19—C20	−178.5 (3)
C1—N2—C5—C6	−5.4 (4)	C18—C19—C20—C21	−0.5 (5)
C2—N2—C5—C6	169.8 (2)	C19—C20—C21—C22	−0.3 (5)
O1—C5—C6—C17	4.0 (5)	C19—C20—C21—Cl1	179.4 (3)
N2—C5—C6—C17	−176.3 (3)	C20—C21—C22—C23	0.5 (5)
O1—C5—C6—S1	−178.3 (3)	Cl1—C21—C22—C23	−179.3 (3)
N2—C5—C6—S1	1.4 (3)	C21—C22—C23—C18	0.1 (5)
C1—S1—C6—C17	179.3 (3)	C19—C18—C23—C22	−0.9 (5)
C1—S1—C6—C5	1.9 (2)	C17—C18—C23—C22	178.7 (3)
C9—O2—C8—O3	3.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···S1	0.93	2.63	3.311 (4)	131
C7—H7C···O3	0.96	2.21	2.915 (6)	129
C14—H14···O1^i	0.93	2.53	3.450 (5)	172

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.