Ethyl 5-(4-chloro-phen-yl)-2-[(Z)-(methoxy-carbon-yl)methyl-ene]-7-methyl-3-oxo-3,5-dihydro-2H-thia-zolo[3,2-a]pyrimi-dine-6-carboxyl-ate.

The title compound, C(19)H(17)ClN(2)O(5)S, was synthesized by the reaction of ethyl 6-(4-chloro-phen-yl)-2-mercapto-4-methyl-1,6-dihydro-pyrimidine-5-carboxyl-ate and dimethyl acetyl-ene-dicarboxyl-ate in methanol. In the mol-ecule, the nearly planar thia-zole ring, with a mean deviation from the plane of 0.0108 (3) Å, is fused with a dihydro-pyrimidine ring in a flattened half-chair conformation.

Related literature

For the biological activity of fused pyrimidine derivatives, see: Ashok et al. (2007 ▶); Monks et al. (1991 ▶). For structures containing a fused pyrimidine ring, see: Liu et al. (2004 ▶); Sridhar et al. (2006 ▶); Hou (2009 ▶).

Experimental

Crystal data

C19H17ClN2O5S

M = 420.86

Triclinic,

a = 9.6687 (19) Å

b = 11.052 (2) Å

c = 11.064 (2) Å

α = 108.04 (3)°

β = 104.70 (3)°

γ = 111.82 (3)°

V = 948.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 113 (2) K

0.20 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.934, T max = 0.966

6937 measured reflections

3324 independent reflections

2622 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.090

S = 1.08

3324 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002451/fl2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002451/fl2231Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H17ClN2O5S	Z = 2
Mr = 420.86	F(000) = 436
Triclinic, P1	Dx = 1.474 Mg m−3
a = 9.6687 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.052 (2) Å	Cell parameters from 3131 reflections
c = 11.064 (2) Å	θ = 2.1–27.9°
α = 108.04 (3)°	µ = 0.35 mm−1
β = 104.70 (3)°	T = 113 K
γ = 111.82 (3)°	Block, yellow
V = 948.2 (3) Å3	0.20 × 0.14 × 0.10 mm

Rigaku Saturn diffractometer	3324 independent reflections
Radiation source: rotating anode	2622 reflections with I > 2σ(I)
confocal	Rint = 0.025
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −11→11
Tmin = 0.934, Tmax = 0.966	k = −13→13
6937 measured reflections	l = −11→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0541P)2] where P = (Fo2 + 2Fc2)/3
3324 reflections	(Δ/σ)max = 0.005
256 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.27994 (5)	0.74177 (5)	0.87884 (4)	0.01936 (13)
Cl1	0.83796 (7)	0.55727 (6)	0.46536 (6)	0.04201 (17)
O1	0.64107 (15)	1.21151 (13)	0.64452 (12)	0.0252 (3)
O2	0.83679 (14)	1.16857 (12)	0.74775 (11)	0.0186 (3)
O3	0.73679 (14)	0.84993 (13)	0.99591 (12)	0.0221 (3)
O4	0.19590 (15)	0.58671 (13)	1.02307 (12)	0.0243 (3)
O5	0.35078 (15)	0.50934 (13)	1.13158 (13)	0.0262 (3)
N1	0.54957 (16)	0.88470 (15)	0.85693 (13)	0.0157 (3)
N2	0.31742 (17)	0.89611 (16)	0.73589 (14)	0.0200 (3)
C1	0.3241 (2)	1.0508 (2)	0.62209 (18)	0.0232 (4)
H1A	0.3709	1.1541	0.6765	0.035*
H1B	0.2115	1.0024	0.6075	0.035*
H1C	0.3300	1.0314	0.5333	0.035*
C2	0.4179 (2)	0.99530 (18)	0.69891 (16)	0.0178 (4)
C3	0.5774 (2)	1.03422 (18)	0.73312 (16)	0.0158 (4)
C4	0.6610 (2)	0.96835 (18)	0.80727 (17)	0.0158 (4)
H4	0.7612	1.0482	0.8889	0.019*
C5	0.3874 (2)	0.85167 (18)	0.81262 (16)	0.0170 (4)
C6	0.6833 (2)	1.14651 (18)	0.70222 (16)	0.0173 (4)
C7	0.9543 (2)	1.27881 (19)	0.72632 (19)	0.0233 (4)
H7A	0.9846	1.3759	0.7921	0.028*
H7B	0.9079	1.2670	0.6320	0.028*
C8	1.1019 (2)	1.2568 (2)	0.7497 (2)	0.0328 (5)
H8A	1.1400	1.2595	0.8401	0.049*
H8B	1.1874	1.3330	0.7455	0.049*
H8C	1.0723	1.1640	0.6786	0.049*
C9	0.7070 (2)	0.86924 (18)	0.71575 (17)	0.0155 (4)
C10	0.8681 (2)	0.89652 (19)	0.76003 (18)	0.0210 (4)
H10	0.9482	0.9778	0.8434	0.025*
C11	0.9108 (2)	0.8038 (2)	0.6811 (2)	0.0253 (4)
H11	1.0189	0.8226	0.7102	0.030*
C12	0.7895 (2)	0.6831 (2)	0.5585 (2)	0.0254 (4)
C13	0.6299 (2)	0.6568 (2)	0.50944 (19)	0.0236 (4)
H13	0.5509	0.5776	0.4242	0.028*
C14	0.5891 (2)	0.75084 (18)	0.58961 (17)	0.0186 (4)
H14	0.4818	0.7340	0.5582	0.022*
C15	0.5986 (2)	0.82795 (18)	0.94441 (16)	0.0167 (4)
C16	0.4553 (2)	0.73775 (18)	0.96435 (17)	0.0178 (4)
C17	0.4656 (2)	0.66465 (18)	1.04032 (17)	0.0193 (4)
H17	0.5632	0.6650	1.0787	0.023*
C18	0.3229 (2)	0.58440 (18)	1.06279 (17)	0.0200 (4)
C19	0.2160 (3)	0.4307 (2)	1.1621 (2)	0.0341 (5)
H19A	0.2063	0.4991	1.2332	0.051*
H19B	0.2374	0.3656	1.1945	0.051*
H19C	0.1156	0.3756	1.0787	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0146 (2)	0.0231 (3)	0.0214 (2)	0.0090 (2)	0.00922 (19)	0.0103 (2)
Cl1	0.0664 (4)	0.0408 (3)	0.0612 (4)	0.0422 (3)	0.0514 (3)	0.0323 (3)
O1	0.0212 (7)	0.0253 (7)	0.0322 (7)	0.0122 (6)	0.0078 (6)	0.0180 (6)
O2	0.0143 (6)	0.0174 (6)	0.0248 (6)	0.0073 (5)	0.0076 (5)	0.0112 (5)
O3	0.0144 (7)	0.0281 (7)	0.0257 (7)	0.0108 (6)	0.0070 (5)	0.0152 (6)
O4	0.0203 (7)	0.0257 (7)	0.0259 (7)	0.0094 (6)	0.0118 (6)	0.0108 (6)
O5	0.0321 (8)	0.0242 (7)	0.0363 (7)	0.0160 (7)	0.0232 (7)	0.0200 (6)
N1	0.0134 (8)	0.0181 (8)	0.0170 (7)	0.0084 (7)	0.0066 (6)	0.0083 (6)
N2	0.0156 (8)	0.0245 (9)	0.0232 (8)	0.0119 (7)	0.0087 (6)	0.0115 (7)
C1	0.0180 (10)	0.0290 (11)	0.0252 (9)	0.0152 (9)	0.0066 (8)	0.0127 (8)
C2	0.0195 (10)	0.0186 (9)	0.0140 (8)	0.0110 (8)	0.0062 (7)	0.0045 (7)
C3	0.0169 (9)	0.0153 (9)	0.0147 (8)	0.0099 (8)	0.0053 (7)	0.0047 (7)
C4	0.0120 (9)	0.0165 (9)	0.0173 (8)	0.0058 (7)	0.0054 (7)	0.0079 (7)
C5	0.0129 (9)	0.0164 (9)	0.0173 (8)	0.0066 (8)	0.0064 (7)	0.0032 (7)
C6	0.0175 (9)	0.0162 (9)	0.0150 (8)	0.0092 (8)	0.0049 (7)	0.0037 (7)
C7	0.0163 (10)	0.0206 (10)	0.0287 (10)	0.0040 (8)	0.0071 (8)	0.0143 (8)
C8	0.0212 (11)	0.0423 (13)	0.0442 (12)	0.0149 (10)	0.0168 (9)	0.0284 (11)
C9	0.0165 (9)	0.0172 (9)	0.0204 (9)	0.0103 (8)	0.0101 (7)	0.0130 (7)
C10	0.0167 (10)	0.0217 (10)	0.0292 (10)	0.0099 (8)	0.0106 (8)	0.0152 (8)
C11	0.0205 (10)	0.0301 (11)	0.0445 (12)	0.0179 (9)	0.0220 (9)	0.0253 (10)
C12	0.0403 (12)	0.0271 (11)	0.0373 (11)	0.0257 (10)	0.0311 (10)	0.0240 (9)
C13	0.0311 (11)	0.0199 (10)	0.0236 (9)	0.0137 (9)	0.0141 (8)	0.0104 (8)
C14	0.0175 (10)	0.0200 (9)	0.0211 (9)	0.0102 (8)	0.0086 (8)	0.0110 (8)
C15	0.0192 (10)	0.0156 (9)	0.0143 (8)	0.0095 (8)	0.0067 (7)	0.0048 (7)
C16	0.0160 (9)	0.0166 (9)	0.0168 (8)	0.0077 (8)	0.0075 (7)	0.0027 (7)
C17	0.0196 (10)	0.0185 (9)	0.0190 (9)	0.0100 (8)	0.0081 (8)	0.0064 (7)
C18	0.0235 (10)	0.0166 (9)	0.0165 (9)	0.0090 (8)	0.0091 (8)	0.0040 (7)
C19	0.0415 (13)	0.0302 (12)	0.0459 (12)	0.0164 (11)	0.0317 (11)	0.0252 (10)

S1—C16	1.7436 (17)	C7—C8	1.507 (2)
S1—C5	1.7582 (17)	C7—H7A	0.9700
Cl1—C12	1.7484 (18)	C7—H7B	0.9700
O1—C6	1.2084 (18)	C8—H8A	0.9600
O2—C6	1.338 (2)	C8—H8B	0.9600
O2—C7	1.4556 (19)	C8—H8C	0.9600
O3—C15	1.2063 (19)	C9—C14	1.383 (3)
O4—C18	1.208 (2)	C9—C10	1.389 (2)
O5—C18	1.3390 (19)	C10—C11	1.388 (2)
O5—C19	1.460 (2)	C10—H10	0.9300
N1—C5	1.380 (2)	C11—C12	1.380 (3)
N1—C15	1.385 (2)	C11—H11	0.9300
N1—C4	1.4804 (19)	C12—C13	1.380 (3)
N2—C5	1.278 (2)	C13—C14	1.390 (2)
N2—C2	1.415 (2)	C13—H13	0.9300
C1—C2	1.506 (2)	C14—H14	0.9300
C1—H1A	0.9600	C15—C16	1.492 (2)
C1—H1B	0.9600	C16—C17	1.344 (2)
C1—H1C	0.9600	C17—C18	1.467 (2)
C2—C3	1.348 (2)	C17—H17	0.9300
C3—C6	1.484 (2)	C19—H19A	0.9600
C3—C4	1.525 (2)	C19—H19B	0.9600
C4—C9	1.525 (2)	C19—H19C	0.9600
C4—H4	0.9800
C16—S1—C5	90.62 (8)	C7—C8—H8C	109.5
C6—O2—C7	116.24 (12)	H8A—C8—H8C	109.5
C18—O5—C19	115.21 (14)	H8B—C8—H8C	109.5
C5—N1—C15	115.79 (14)	C14—C9—C10	119.53 (15)
C5—N1—C4	121.86 (13)	C14—C9—C4	120.55 (14)
C15—N1—C4	122.26 (13)	C10—C9—C4	119.91 (16)
C5—N2—C2	116.82 (14)	C11—C10—C9	120.70 (18)
C2—C1—H1A	109.5	C11—C10—H10	119.7
C2—C1—H1B	109.5	C9—C10—H10	119.7
H1A—C1—H1B	109.5	C12—C11—C10	118.56 (16)
C2—C1—H1C	109.5	C12—C11—H11	120.7
H1A—C1—H1C	109.5	C10—C11—H11	120.7
H1B—C1—H1C	109.5	C11—C12—C13	121.80 (16)
C3—C2—N2	122.50 (14)	C11—C12—Cl1	119.10 (14)
C3—C2—C1	126.35 (16)	C13—C12—Cl1	119.07 (16)
N2—C2—C1	111.13 (14)	C12—C13—C14	118.87 (18)
C2—C3—C6	121.48 (14)	C12—C13—H13	120.6
C2—C3—C4	122.65 (15)	C14—C13—H13	120.6
C6—C3—C4	115.87 (14)	C9—C14—C13	120.43 (16)
N1—C4—C3	108.32 (12)	C9—C14—H14	119.8
N1—C4—C9	109.42 (13)	C13—C14—H14	119.8
C3—C4—C9	113.84 (12)	O3—C15—N1	124.33 (15)
N1—C4—H4	108.4	O3—C15—C16	126.19 (14)
C3—C4—H4	108.4	N1—C15—C16	109.48 (13)
C9—C4—H4	108.4	C17—C16—C15	122.53 (15)
N2—C5—N1	126.49 (15)	C17—C16—S1	125.85 (14)
N2—C5—S1	121.06 (13)	C15—C16—S1	111.62 (11)
N1—C5—S1	112.42 (11)	C16—C17—C18	120.08 (15)
O1—C6—O2	123.10 (15)	C16—C17—H17	120.0
O1—C6—C3	126.17 (15)	C18—C17—H17	120.0
O2—C6—C3	110.73 (13)	O4—C18—O5	124.64 (15)
O2—C7—C8	106.32 (13)	O4—C18—C17	123.25 (15)
O2—C7—H7A	110.5	O5—C18—C17	112.11 (14)
C8—C7—H7A	110.5	O5—C19—H19A	109.5
O2—C7—H7B	110.5	O5—C19—H19B	109.5
C8—C7—H7B	110.5	H19A—C19—H19B	109.5
H7A—C7—H7B	108.7	O5—C19—H19C	109.5
C7—C8—H8A	109.5	H19A—C19—H19C	109.5
C7—C8—H8B	109.5	H19B—C19—H19C	109.5
H8A—C8—H8B	109.5
C5—N2—C2—C3	4.8 (2)	C3—C4—C9—C14	−56.3 (2)
C5—N2—C2—C1	−173.86 (14)	N1—C4—C9—C10	−114.05 (16)
N2—C2—C3—C6	−175.50 (14)	C3—C4—C9—C10	124.61 (16)
C1—C2—C3—C6	2.9 (3)	C14—C9—C10—C11	−1.9 (2)
N2—C2—C3—C4	3.6 (2)	C4—C9—C10—C11	177.13 (13)
C1—C2—C3—C4	−178.02 (15)	C9—C10—C11—C12	−0.7 (2)
C5—N1—C4—C3	12.4 (2)	C10—C11—C12—C13	3.4 (2)
C15—N1—C4—C3	−171.19 (13)	C10—C11—C12—Cl1	−174.78 (11)
C5—N1—C4—C9	−112.22 (16)	C11—C12—C13—C14	−3.3 (2)
C15—N1—C4—C9	64.19 (19)	Cl1—C12—C13—C14	174.86 (12)
C2—C3—C4—N1	−11.4 (2)	C10—C9—C14—C13	2.0 (2)
C6—C3—C4—N1	167.76 (13)	C4—C9—C14—C13	−177.04 (13)
C2—C3—C4—C9	110.58 (18)	C12—C13—C14—C9	0.5 (2)
C6—C3—C4—C9	−70.30 (19)	C5—N1—C15—O3	−177.63 (15)
C2—N2—C5—N1	−3.7 (2)	C4—N1—C15—O3	5.8 (2)
C2—N2—C5—S1	174.06 (11)	C5—N1—C15—C16	2.09 (19)
C15—N1—C5—N2	177.49 (15)	C4—N1—C15—C16	−174.52 (13)
C4—N1—C5—N2	−5.9 (3)	O3—C15—C16—C17	−2.8 (3)
C15—N1—C5—S1	−0.44 (18)	N1—C15—C16—C17	177.46 (15)
C4—N1—C5—S1	176.18 (11)	O3—C15—C16—S1	176.86 (14)
C16—S1—C5—N2	−179.16 (14)	N1—C15—C16—S1	−2.86 (16)
C16—S1—C5—N1	−1.10 (13)	C5—S1—C16—C17	−178.09 (16)
C7—O2—C6—O1	1.0 (2)	C5—S1—C16—C15	2.24 (12)
C7—O2—C6—C3	−178.78 (13)	C15—C16—C17—C18	176.57 (14)
C2—C3—C6—O1	−0.9 (3)	S1—C16—C17—C18	−3.1 (2)
C4—C3—C6—O1	180.00 (15)	C19—O5—C18—O4	−2.1 (2)
C2—C3—C6—O2	178.93 (14)	C19—O5—C18—C17	177.95 (14)
C4—C3—C6—O2	−0.21 (19)	C16—C17—C18—O4	−4.6 (3)
C6—O2—C7—C8	−165.55 (14)	C16—C17—C18—O5	175.35 (15)
N1—C4—C9—C14	65.01 (17)