Methyl 5-(4-hy­droxy-3-meth­oxy­phen­yl)-2-(4-meth­oxy­benzyl­idene)-7-methyl-3-oxo-2,3-dihydro-5H-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

Nagarajaiah, H.; Begum, N.S.

doi:10.1107/S1600536811048987

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3444

https://doi.org/10.1107/S1600536811048987

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Methyl 5-(4-hydroxy-3-methoxyphenyl)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate

H. Nagarajaiah ^a and Noor Shahina Begum ^a ^*

^aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, India
^*Correspondence e-mail: noorsb@rediffmail.com

(Received 24 October 2011; accepted 17 November 2011; online 25 November 2011)

In the title compound, C₂₄H₂₂N₂O₆S, a pyrimidine ring substituted with 4-hydroxy-3-methoxyphenyl is fused with a thiazole ring. The 4-hydroxy-3-methoxyphenyl group is positioned axially to the pyrimidine ring, making a dihedral angle 85.36 (7)°. The pyrimidine ring adopts a twist boat conformation. In the crystal, O—H⋯N interactions result in a chain running along the b axis. The carbonyl O atom bonded to the thiazole ring is involved in two C—H⋯O hydrogen-bond interactions forming centrosymmetric dimers; the ten- and six-membered rings resulting from these interactions have R₂²(10) and R₁²(6) motifs, respectively.

Related literature

For pharmacological properties of pyrimidine derivatives, see: Alam et al. (2010 ). For related structures, see: Jotani et al. (2010 ). For graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₄H₂₂N₂O₆S
M_r = 466.50
Triclinic, $[P \overline 1]$
a = 6.8096 (12) Å
b = 9.9343 (18) Å
c = 16.246 (3) Å
α = 86.816 (3)°
β = 85.588 (3)°
γ = 81.318 (3)°
V = 1082.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.966, T_max = 0.969
6570 measured reflections
4581 independent reflections
3452 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.279
S = 1.33
4581 reflections
303 parameters
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯N2ⁱ	0.82	2.01	2.783 (4)	156
C10—H10⋯O2ⁱⁱ	0.93	2.55	3.425 (4)	156
C12—H12⋯O2ⁱⁱ	0.93	2.67	3.499 (4)	149
C1—H1A⋯O6ⁱⁱⁱ	0.96	2.57	3.444 (5)	152
C17—H17C⋯O2^iv	0.96	2.47	3.429 (5)	179
Symmetry codes: (i) x, y-1, z; (ii) -x, -y, -z+1; (iii) -x, -y, -z; (iv) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811048987/pv2473sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048987/pv2473Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048987/pv2473Isup3.cml

checkCIF report

Comment top

Pyrimidine derivatives are of interest because of their pharmacological properties (Alam et al., 2010).

The central pyrimidine ring with a chiral C5 atom is significantly puckered and adopts a conformation which is best described as an intermediate between a boat and a screw boat form as seen earlier (Jotani et al., 2010). The atoms C5 and N1 deviate from the mean plane C6/C7/N2/C8 by 0.1024 (3) and -0.0602 (3) Å, respectively, indicating that the conformation of the pyrimidine ring is that of a twisted boat. In the molecule, The fused thiazole-pyrimidine ring is coplanar with benzylidene ring with dihedral angle 5.19 (7)°. The dihedral angle between the thiazolopyrimidine ring and 4-hydroxy-3-methoxy-phenyl group is 85.36 (7)°. The crystal structure is stabilized by a strong intermolecular O—H···N hydrogen bond resulting in a one dimensional chain of molecules along the b axis. The structure is further consolidated by C—H···O type intermolecular interactions, involving carbonyl O2 atom, forming centrosymmetric dimers; the ten and 6 membered rings thus resulting from these interactions can be described as R²₂(10) and R²₁(6) motifs in graph-set notations (Bernstein et al., 1995).

Related literature top

For pharmacological properties of pyrimidine derivatives, see: Alam et al. (2010). For related structures, see: Jotani et al. (2010). For graph-set motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 4-(4-hydroxy-3-methoxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro -pyrimidine-5-carboxylic acid methyl ester (0.01 mol), chloroaceticacid (0.01 mol), 4-methoxy benzaldehyde (0.01 mol) and sodium acetate (1.5 g) in a mixture of glacial acetic acid and acetic anhydride (25 ml; 1:1) was refluxed for 8–10 h.The reaction mixture was concentrated and the solid thus obtained was filtered and recrystallized from ethyl acetate to get the title compound. (78% yield, mp 427 K). The compound was recrystallized by slow evaporation of an ethyl acetate-ethanol (3:2) solution, yielding pale yellow single crystals suitable for X-ray diffraction studies.

Structure description top

Pyrimidine derivatives are of interest because of their pharmacological properties (Alam et al., 2010).

For pharmacological properties of pyrimidine derivatives, see: Alam et al. (2010). For related structures, see: Jotani et al. (2010). For graph-set motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) view of the title compound, showing 50% probability ellipsoids and the atom numbering scheme.
	Fig. 2. A unit cell packing of the title compound showing intermolecular interactions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded for clarity.

Methyl 5-(4-hydroxy-3-methoxyphenyl)-2-(4-methoxybenzylidene)-7-methyl-3-oxo- 2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate top

Crystal data top

C₂₄H₂₂N₂O₆S	V = 1082.1 (3) Å³
M_r = 466.50	Z = 2
Triclinic, P1	F(000) = 488
Hall symbol: -P 1	D_x = 1.432 Mg m⁻³
a = 6.8096 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9343 (18) Å	µ = 0.20 mm⁻¹
c = 16.246 (3) Å	T = 296 K
α = 86.816 (3)°	Block, yellow
β = 85.588 (3)°	0.18 × 0.16 × 0.16 mm
γ = 81.318 (3)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	4581 independent reflections
Radiation source: fine-focus sealed tube	3452 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→8
T_min = 0.966, T_max = 0.969	k = −12→10
6570 measured reflections	l = −20→20

Refinement top

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.279	H-atom parameters constrained
S = 1.33	w = 1/[σ²(F_o²) + (0.1558P)²] where P = (F_o² + 2F_c²)/3
4581 reflections	(Δ/σ)_max < 0.001
303 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₂₄H₂₂N₂O₆S	γ = 81.318 (3)°
M_r = 466.50	V = 1082.1 (3) Å³
Triclinic, P1	Z = 2
a = 6.8096 (12) Å	Mo Kα radiation
b = 9.9343 (18) Å	µ = 0.20 mm⁻¹
c = 16.246 (3) Å	T = 296 K
α = 86.816 (3)°	0.18 × 0.16 × 0.16 mm
β = 85.588 (3)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	4581 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3452 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.969	R_int = 0.018
6570 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.279	H-atom parameters constrained
S = 1.33	Δρ_max = 0.69 e Å⁻³
4581 reflections	Δρ_min = −0.62 e Å⁻³
303 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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

	x	y	z	U_iso*/U_eq
S1	0.15410 (13)	0.32220 (9)	0.29148 (5)	0.0312 (3)
O6	0.0905 (4)	−0.4233 (2)	0.13814 (16)	0.0352 (6)
H6	0.0110	−0.4779	0.1447	0.053*
O2	−0.1068 (4)	0.0292 (2)	0.39078 (14)	0.0314 (6)
N1	−0.1155 (4)	0.1703 (3)	0.27435 (16)	0.0257 (6)
O3	−0.6100 (4)	0.0792 (3)	0.16436 (16)	0.0372 (6)
N2	−0.0791 (5)	0.3389 (3)	0.16660 (17)	0.0299 (7)
O1	0.8821 (4)	0.3698 (3)	0.54235 (17)	0.0415 (7)
C6	−0.3314 (5)	0.1959 (3)	0.15964 (19)	0.0263 (7)
O5	−0.2673 (4)	−0.3960 (2)	0.22167 (17)	0.0365 (6)
C5	−0.2615 (5)	0.1047 (3)	0.2339 (2)	0.0276 (7)
H5	−0.3765	0.0977	0.2733	0.033*
C19	−0.2694 (5)	−0.1507 (3)	0.2295 (2)	0.0276 (7)
H19	−0.3925	−0.1391	0.2593	0.033*
O4	−0.5284 (4)	0.1916 (3)	0.04588 (15)	0.0465 (8)
C21	0.0002 (5)	−0.2994 (3)	0.1616 (2)	0.0288 (7)
C18	−0.1708 (5)	−0.0377 (3)	0.20939 (19)	0.0264 (7)
C3	−0.0444 (5)	0.1214 (3)	0.3500 (2)	0.0281 (7)
C12	0.4787 (5)	0.1626 (4)	0.5346 (2)	0.0298 (7)
H12	0.4232	0.0936	0.5647	0.036*
C8	−0.0300 (5)	0.2758 (3)	0.2354 (2)	0.0281 (7)
C20	−0.1849 (5)	−0.2791 (3)	0.20538 (19)	0.0271 (7)
C22	0.0966 (5)	−0.1868 (3)	0.1404 (2)	0.0313 (8)
H22	0.2194	−0.1982	0.1103	0.038*
C2	0.1203 (5)	0.1940 (3)	0.3687 (2)	0.0297 (7)
C10	0.2243 (5)	0.1629 (3)	0.4359 (2)	0.0276 (7)
H10	0.1809	0.0946	0.4709	0.033*
C11	0.3928 (5)	0.2179 (4)	0.4631 (2)	0.0315 (8)
C7	−0.2434 (5)	0.3037 (3)	0.1307 (2)	0.0284 (7)
C14	0.7248 (5)	0.3131 (4)	0.5199 (2)	0.0321 (8)
C23	0.0097 (5)	−0.0576 (4)	0.1639 (2)	0.0324 (8)
H23	0.0747	0.0168	0.1487	0.039*
C13	0.6444 (5)	0.2068 (4)	0.5625 (2)	0.0335 (8)
H13	0.7015	0.1654	0.6095	0.040*
C1	−0.3048 (6)	0.4018 (4)	0.0603 (2)	0.0382 (9)
H1A	−0.2234	0.3761	0.0112	0.057*
H1B	−0.2881	0.4922	0.0735	0.057*
H1C	−0.4419	0.3997	0.0514	0.057*
C4	−0.5039 (5)	0.1509 (4)	0.1248 (2)	0.0321 (8)
C15	0.6422 (6)	0.3702 (4)	0.4484 (2)	0.0405 (9)
H15	0.6966	0.4408	0.4194	0.049*
C17	0.9714 (6)	0.3169 (4)	0.6163 (2)	0.0397 (9)
H17A	0.8779	0.3364	0.6630	0.060*
H17B	1.0875	0.3587	0.6223	0.060*
H17C	1.0090	0.2201	0.6135	0.060*
C16	0.4802 (6)	0.3238 (4)	0.4194 (2)	0.0375 (9)
H16	0.4281	0.3623	0.3708	0.045*
C24	−0.4702 (6)	−0.3847 (4)	0.2508 (3)	0.0441 (10)
H24A	−0.4846	−0.3583	0.3071	0.066*
H24B	−0.5158	−0.4710	0.2476	0.066*
H24C	−0.5479	−0.3171	0.2173	0.066*
C9	−0.7019 (7)	0.1526 (6)	0.0106 (3)	0.0592 (14)
H9A	−0.7048	0.0570	0.0218	0.089*
H9B	−0.6936	0.1714	−0.0480	0.089*
H9C	−0.8212	0.2037	0.0349	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0364 (5)	0.0289 (5)	0.0312 (5)	−0.0120 (4)	−0.0098 (4)	0.0032 (3)
O6	0.0355 (14)	0.0286 (13)	0.0421 (15)	−0.0088 (10)	0.0013 (11)	−0.0022 (11)
O2	0.0380 (14)	0.0306 (13)	0.0281 (12)	−0.0132 (11)	−0.0077 (10)	0.0057 (10)
N1	0.0267 (15)	0.0245 (14)	0.0270 (14)	−0.0077 (11)	−0.0056 (11)	0.0039 (11)
O3	0.0300 (14)	0.0459 (16)	0.0385 (14)	−0.0149 (12)	−0.0089 (11)	0.0070 (12)
N2	0.0384 (17)	0.0251 (15)	0.0287 (15)	−0.0107 (12)	−0.0077 (12)	0.0000 (11)
O1	0.0365 (15)	0.0447 (16)	0.0481 (16)	−0.0150 (12)	−0.0171 (12)	−0.0011 (13)
C6	0.0282 (17)	0.0274 (17)	0.0242 (16)	−0.0065 (13)	−0.0064 (13)	0.0047 (13)
O5	0.0351 (14)	0.0282 (13)	0.0480 (15)	−0.0142 (11)	0.0049 (11)	−0.0023 (11)
C5	0.0259 (17)	0.0287 (17)	0.0308 (17)	−0.0114 (13)	−0.0068 (13)	0.0036 (13)
C19	0.0250 (17)	0.0305 (18)	0.0296 (17)	−0.0111 (13)	−0.0034 (13)	0.0005 (13)
O4	0.0453 (17)	0.070 (2)	0.0309 (14)	−0.0285 (15)	−0.0194 (12)	0.0146 (13)
C21	0.0297 (18)	0.0279 (17)	0.0298 (17)	−0.0072 (13)	−0.0065 (13)	0.0030 (13)
C18	0.0270 (17)	0.0288 (17)	0.0250 (16)	−0.0072 (13)	−0.0089 (12)	0.0029 (13)
C3	0.0309 (18)	0.0264 (17)	0.0276 (17)	−0.0049 (14)	−0.0067 (13)	0.0002 (13)
C12	0.0302 (18)	0.0326 (18)	0.0280 (17)	−0.0071 (14)	−0.0057 (13)	−0.0014 (14)
C8	0.0279 (18)	0.0255 (16)	0.0308 (17)	−0.0032 (13)	−0.0015 (13)	−0.0030 (13)
C20	0.0340 (19)	0.0248 (17)	0.0253 (16)	−0.0122 (14)	−0.0055 (13)	0.0009 (13)
C22	0.0272 (18)	0.0269 (18)	0.0398 (19)	−0.0058 (13)	−0.0019 (14)	0.0028 (14)
C2	0.0319 (19)	0.0269 (17)	0.0324 (17)	−0.0098 (14)	−0.0022 (14)	−0.0064 (14)
C10	0.0296 (18)	0.0292 (18)	0.0258 (16)	−0.0086 (14)	−0.0056 (13)	−0.0011 (13)
C11	0.0317 (19)	0.0308 (18)	0.0329 (18)	−0.0074 (14)	−0.0018 (14)	−0.0001 (14)
C7	0.0281 (18)	0.0276 (17)	0.0303 (17)	−0.0035 (13)	−0.0096 (13)	0.0007 (13)
C14	0.0293 (19)	0.0285 (18)	0.0396 (19)	−0.0040 (14)	−0.0073 (14)	−0.0034 (15)
C23	0.0272 (18)	0.0298 (18)	0.043 (2)	−0.0118 (14)	−0.0066 (14)	0.0030 (15)
C13	0.0300 (19)	0.0342 (19)	0.0354 (19)	0.0006 (14)	−0.0067 (14)	−0.0023 (15)
C1	0.047 (2)	0.0300 (19)	0.039 (2)	−0.0091 (16)	−0.0150 (17)	0.0093 (16)
C4	0.0279 (18)	0.0346 (19)	0.0338 (18)	−0.0040 (14)	−0.0063 (14)	0.0029 (15)
C15	0.040 (2)	0.039 (2)	0.046 (2)	−0.0174 (17)	−0.0140 (17)	0.0082 (17)
C17	0.034 (2)	0.049 (2)	0.039 (2)	−0.0080 (17)	−0.0112 (16)	−0.0030 (17)
C16	0.044 (2)	0.0294 (19)	0.041 (2)	−0.0110 (16)	−0.0120 (17)	0.0061 (15)
C24	0.035 (2)	0.034 (2)	0.063 (3)	−0.0134 (16)	0.0078 (18)	−0.0012 (18)
C9	0.048 (3)	0.095 (4)	0.042 (2)	−0.032 (3)	−0.021 (2)	0.017 (2)

Geometric parameters (Å, º) top

S1—C8	1.735 (3)	C12—C13	1.387 (5)
S1—C2	1.765 (4)	C12—C11	1.388 (5)
O6—C21	1.352 (4)	C12—H12	0.9300
O6—H6	0.8200	C22—C23	1.391 (5)
O2—C3	1.210 (4)	C22—H22	0.9300
N1—C8	1.376 (4)	C2—C10	1.343 (5)
N1—C3	1.391 (4)	C10—C11	1.451 (4)
N1—C5	1.479 (4)	C10—H10	0.9300
O3—C4	1.215 (4)	C11—C16	1.416 (5)
N2—C8	1.292 (4)	C7—C1	1.503 (5)
N2—C7	1.398 (4)	C14—C15	1.386 (5)
O1—C14	1.364 (4)	C14—C13	1.389 (5)
O1—C17	1.427 (4)	C23—H23	0.9300
C6—C7	1.350 (5)	C13—H13	0.9300
C6—C4	1.479 (5)	C1—H1A	0.9600
C6—C5	1.530 (4)	C1—H1B	0.9600
O5—C20	1.369 (4)	C1—H1C	0.9600
O5—C24	1.416 (4)	C15—C16	1.382 (5)
C5—C18	1.518 (5)	C15—H15	0.9300
C5—H5	0.9800	C17—H17A	0.9600
C19—C20	1.382 (5)	C17—H17B	0.9600
C19—C18	1.404 (4)	C17—H17C	0.9600
C19—H19	0.9300	C16—H16	0.9300
O4—C4	1.338 (4)	C24—H24A	0.9600
O4—C9	1.463 (4)	C24—H24B	0.9600
C21—C20	1.392 (5)	C24—H24C	0.9600
C21—C22	1.395 (4)	C9—H9A	0.9600
C18—C23	1.378 (5)	C9—H9B	0.9600
C3—C2	1.480 (4)	C9—H9C	0.9600

C8—S1—C2	91.56 (16)	C12—C11—C16	117.3 (3)
C21—O6—H6	109.5	C12—C11—C10	119.2 (3)
C8—N1—C3	116.4 (3)	C16—C11—C10	123.6 (3)
C8—N1—C5	121.3 (3)	C6—C7—N2	121.8 (3)
C3—N1—C5	122.1 (3)	C6—C7—C1	127.0 (3)
C8—N2—C7	117.4 (3)	N2—C7—C1	111.2 (3)
C14—O1—C17	117.6 (3)	O1—C14—C15	115.0 (3)
C7—C6—C4	125.2 (3)	O1—C14—C13	125.7 (3)
C7—C6—C5	122.9 (3)	C15—C14—C13	119.3 (3)
C4—C6—C5	111.8 (3)	C18—C23—C22	121.2 (3)
C20—O5—C24	118.5 (3)	C18—C23—H23	119.4
N1—C5—C18	110.5 (3)	C22—C23—H23	119.4
N1—C5—C6	108.4 (2)	C12—C13—C14	119.7 (3)
C18—C5—C6	112.2 (3)	C12—C13—H13	120.2
N1—C5—H5	108.6	C14—C13—H13	120.2
C18—C5—H5	108.6	C7—C1—H1A	109.5
C6—C5—H5	108.6	C7—C1—H1B	109.5
C20—C19—C18	120.5 (3)	H1A—C1—H1B	109.5
C20—C19—H19	119.8	C7—C1—H1C	109.5
C18—C19—H19	119.8	H1A—C1—H1C	109.5
C4—O4—C9	115.8 (3)	H1B—C1—H1C	109.5
O6—C21—C20	123.0 (3)	O3—C4—O4	123.1 (3)
O6—C21—C22	118.4 (3)	O3—C4—C6	122.2 (3)
C20—C21—C22	118.6 (3)	O4—C4—C6	114.6 (3)
C23—C18—C19	118.5 (3)	C16—C15—C14	121.0 (3)
C23—C18—C5	119.9 (3)	C16—C15—H15	119.5
C19—C18—C5	121.6 (3)	C14—C15—H15	119.5
O2—C3—N1	123.1 (3)	O1—C17—H17A	109.5
O2—C3—C2	127.1 (3)	O1—C17—H17B	109.5
N1—C3—C2	109.7 (3)	H17A—C17—H17B	109.5
C13—C12—C11	122.2 (3)	O1—C17—H17C	109.5
C13—C12—H12	118.9	H17A—C17—H17C	109.5
C11—C12—H12	118.9	H17B—C17—H17C	109.5
N2—C8—N1	126.2 (3)	C15—C16—C11	120.5 (3)
N2—C8—S1	121.8 (3)	C15—C16—H16	119.7
N1—C8—S1	112.0 (2)	C11—C16—H16	119.7
O5—C20—C19	125.4 (3)	O5—C24—H24A	109.5
O5—C20—C21	113.7 (3)	O5—C24—H24B	109.5
C19—C20—C21	120.9 (3)	H24A—C24—H24B	109.5
C23—C22—C21	120.2 (3)	O5—C24—H24C	109.5
C23—C22—H22	119.9	H24A—C24—H24C	109.5
C21—C22—H22	119.9	H24B—C24—H24C	109.5
C10—C2—C3	122.8 (3)	O4—C9—H9A	109.5
C10—C2—S1	126.9 (3)	O4—C9—H9B	109.5
C3—C2—S1	110.3 (2)	H9A—C9—H9B	109.5
C2—C10—C11	131.0 (3)	O4—C9—H9C	109.5
C2—C10—H10	114.5	H9A—C9—H9C	109.5
C11—C10—H10	114.5	H9B—C9—H9C	109.5

C8—N1—C5—C18	108.8 (3)	N1—C3—C2—C10	−176.5 (3)
C3—N1—C5—C18	−65.4 (4)	O2—C3—C2—S1	−179.2 (3)
C8—N1—C5—C6	−14.4 (4)	N1—C3—C2—S1	3.7 (4)
C3—N1—C5—C6	171.3 (3)	C8—S1—C2—C10	177.4 (3)
C7—C6—C5—N1	10.4 (5)	C8—S1—C2—C3	−2.8 (3)
C4—C6—C5—N1	−169.6 (3)	C3—C2—C10—C11	177.5 (3)
C7—C6—C5—C18	−111.9 (4)	S1—C2—C10—C11	−2.7 (6)
C4—C6—C5—C18	68.1 (4)	C13—C12—C11—C16	−0.6 (6)
C20—C19—C18—C23	1.1 (5)	C13—C12—C11—C10	177.6 (3)
C20—C19—C18—C5	179.0 (3)	C2—C10—C11—C12	−177.3 (4)
N1—C5—C18—C23	−51.6 (4)	C2—C10—C11—C16	0.8 (6)
C6—C5—C18—C23	69.4 (4)	C4—C6—C7—N2	−179.3 (3)
N1—C5—C18—C19	130.5 (3)	C5—C6—C7—N2	0.7 (5)
C6—C5—C18—C19	−108.4 (3)	C4—C6—C7—C1	2.2 (6)
C8—N1—C3—O2	179.9 (3)	C5—C6—C7—C1	−177.8 (3)
C5—N1—C3—O2	−5.6 (5)	C8—N2—C7—C6	−9.0 (5)
C8—N1—C3—C2	−2.9 (4)	C8—N2—C7—C1	169.7 (3)
C5—N1—C3—C2	171.6 (3)	C17—O1—C14—C15	179.0 (3)
C7—N2—C8—N1	4.7 (5)	C17—O1—C14—C13	−0.7 (5)
C7—N2—C8—S1	−173.2 (2)	C19—C18—C23—C22	−2.0 (5)
C3—N1—C8—N2	−177.3 (3)	C5—C18—C23—C22	−179.9 (3)
C5—N1—C8—N2	8.1 (5)	C21—C22—C23—C18	0.9 (5)
C3—N1—C8—S1	0.8 (4)	C11—C12—C13—C14	2.3 (6)
C5—N1—C8—S1	−173.7 (2)	O1—C14—C13—C12	177.3 (3)
C2—S1—C8—N2	179.4 (3)	C15—C14—C13—C12	−2.3 (6)
C2—S1—C8—N1	1.2 (3)	C9—O4—C4—O3	4.3 (6)
C24—O5—C20—C19	13.4 (5)	C9—O4—C4—C6	−178.0 (4)
C24—O5—C20—C21	−167.5 (3)	C7—C6—C4—O3	−159.7 (4)
C18—C19—C20—O5	179.9 (3)	C5—C6—C4—O3	20.3 (5)
C18—C19—C20—C21	0.8 (5)	C7—C6—C4—O4	22.6 (5)
O6—C21—C20—O5	−0.6 (5)	C5—C6—C4—O4	−157.4 (3)
C22—C21—C20—O5	178.9 (3)	O1—C14—C15—C16	−179.0 (4)
O6—C21—C20—C19	178.6 (3)	C13—C14—C15—C16	0.6 (6)
C22—C21—C20—C19	−1.9 (5)	C14—C15—C16—C11	1.1 (6)
O6—C21—C22—C23	−179.4 (3)	C12—C11—C16—C15	−1.0 (6)
C20—C21—C22—C23	1.0 (5)	C10—C11—C16—C15	−179.2 (4)
O2—C3—C2—C10	0.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···N2ⁱ	0.82	2.01	2.783 (4)	156
C10—H10···O2ⁱⁱ	0.93	2.55	3.425 (4)	156
C12—H12···O2ⁱⁱ	0.93	2.67	3.499 (4)	149
C1—H1A···O6ⁱⁱⁱ	0.96	2.57	3.444 (5)	152
C17—H17C···O2^iv	0.96	2.47	3.429 (5)	179

Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+1; (iii) −x, −y, −z; (iv) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂N₂O₆S
M_r	466.50
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.8096 (12), 9.9343 (18), 16.246 (3)
α, β, γ (°)	86.816 (3), 85.588 (3), 81.318 (3)
V (Å³)	1082.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.18 × 0.16 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD detector
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.966, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	6570, 4581, 3452
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.279, 1.33
No. of reflections	4581
No. of parameters	303
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.62

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···N2ⁱ	0.820	2.010	2.783 (4)	156
C10—H10···O2ⁱⁱ	0.930	2.550	3.425 (4)	156
C12—H12···O2ⁱⁱ	0.930	2.670	3.499 (4)	149
C1—H1A···O6ⁱⁱⁱ	0.960	2.566	3.444 (5)	152
C17—H17C···O2^iv	0.960	2.469	3.429 (5)	179

Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+1; (iii) −x, −y, −z; (iv) −x+1, −y, −z+1.

Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance and the Department of Science and Technology, (DST), India, for the data-collection facility under the IRHPA–DST program.

References

Alam, O., Khan, S. A., Siddiqui, N. & Ahsan, W. (2010). Med. Chem. Res. 19, 1245–1258. Web of Science CrossRef CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Jotani, M. M., Baldaniya, B. B. & Jasinski, J. P. (2010). Acta Cryst. E66, o599–o600. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 5-(4-hy­dr­oxy-3-meth­­oxy­phen­yl)-2-(4-meth­­oxy­benzyl­­idene)-7-methyl-3-oxo-2,3-di­hydro-5H-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 5-(4-hydroxy-3-methoxyphenyl)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate