Methyl 5-(4-acet­oxy­phen­yl)-2-(2-bromo­benzyl­idine)-7-methyl-3-oxo-2,3-di­hydro-5H-1,3-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

Fathima, N.; Nagarajaiah, H.; Begum, N.S.

doi:10.1107/S1600536813019132

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1262

doi:10.1107/S1600536813019132

Open

access

Methyl 5-(4-acetoxyphenyl)-2-(2-bromobenzylidine)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate

Nikhath Fathima,^a H. Nagarajaiah ^a and Noor Shahina Begum ^a ^*

^aDepartment of Chemistry, Bangalore University, Bangalore 560 001, India
^*Correspondence e-mail: noorsb@rediffmail.com, noorsb05@gmail.com

(Received 24 June 2013; accepted 10 July 2013; online 13 July 2013)

In the title molecule, C₂₄H₁₉BrN₂O₅S, the pyrimidine ring is in a flattened half-chair conformation and the 4-acetoxyphenyl group is substituted axially to this ring. The thiazole ring is essentially planar [with a maximum deviation of 0.012 (2) Å for the N atom] and forms dihedral angles of 17.65 (13) and 88.95 (11)° with the bromo- and acetoxy-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 81.84 (13) Å. In the crystal, pairs of weak C—H⋯O hydrogen bonds lead to the formation of inversion dimers. A weak C—H⋯π interaction and π–π stacking interactions with centroid–centroid distances of 3.5903 (14) Å are observed.

Related literature

For the biological activity of dihydropyrimidines, see: Alam et al. (2010 ); Kappe (2000 ); Atwal et al. (1991 ); Rovnyak et al. (1992 ). For related structures, see: Nagarajaiah et al. (2011 , 2012 ). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₄H₁₉BrN₂O₅S
M_r = 527.38
Triclinic, $[P \overline 1]$
a = 7.6018 (5) Å
b = 11.9648 (7) Å
c = 14.0877 (9) Å
α = 106.425 (1)°
β = 104.700 (2)°
γ = 106.296 (1)°
V = 1099.75 (12) Å³
Z = 2
Mo Kα radiation
μ = 2.00 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 = 0.714, T_max = 0.740
9029 measured reflections
4777 independent reflections
3989 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.096
S = 1.05
4777 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C5–C7/C9/N1/N2 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1ⁱ	0.93	2.60	3.343 (4)	138
C10—H10⋯Cgⁱⁱ	0.93	2.61	3.513 (4)	147
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x-1, -y-1, -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 for Windows (Farrugia, 2012 ) and CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813019132/lh5628sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019132/lh5628Isup2.hkl

checkCIF report

Comment top

Dihydropyrimidines (DHPM) exhibit a broad range of therapeutic and pharmacological properties (Alam et al., 2010). These non-planar heterocyclic compounds have interesting multifaceted pharmacological profiles such as calcium channel modulation, antitumor, antiviral, antibacterial, anti-inflammatory and antimicrobial activities (Kappe et al., 2000; Atwal et al.. 1991). In addition, a few DHPM derivatives have even emerged as orally active antihypertensive agents (Rovnyak et al., 1992).

The molecular structure of the title compound is shown in Fig. 1. The 4-acetoxy substituted benzene ring is axially substituted to the pyrimidine ring. The central pyrimidine ring adopts a half chair conformation with deviations of 0.107 (2) and -0.200 (2) Å for N1 and C5 respectively from the remaining four ring atoms (C6/C7/C9/N2). In the crystal, pairs of weak C—H···O hydrogen bonds form inversion dimers with a graph set notation of R²₂(16) (Bernstein et al., 1995) as shown in Fig. 2. The crystal structure of the title compound shows different type of intermolecular interactions compared to a similar structure reported earlier (Nagarajaiah et al., 2012). In addition, there are intermolecular π···π interactions between inversion-related thiazole rings with a centroid to centroid distance of 3.5903 (14)Å. A weak C—H···π(ring) interaction is also observed (see Table 1, where Cg is the centroid of the C5/C6/C7/N2/C9/N1 ring). Another example of a related crystal structure has been published in the literature (Nagarajaiah et al., 2011).

Related literature top

For the biological activity of dihydropyrimidines, see: Alam et al. (2010); Kappe et al. (2000); Atwal et al. (1991); Rovnyak et al. (1992). For related structures, see: Nagarajaiah et al. (2011, 2012). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995).

Experimental top

The compound 2-(2-bromo-benzylidene)-4-(4-hydroxy-phenyl)6-methyl-3-oxo-2,3-dihydro-thieno[2,3-bpyridine-5-carboxylic acid (2.0 g) was mixed with acetic anhydride (10 ml) and refluxed for about 4 h. The reaction mixture was cooled and diluted by the addition of water (20 ml). The solid separated was washed with water, filtered, and dried (Yield: 2.63 g, 80% and mp 418 K). Pale yellow crystals suitable for diffraction were obtained by slow evaporation of a solution of the title compound in chloroform.

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 for Windows (Farrugia, 2012) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability ellipsoids.
	Fig. 2. The packing of the title compound showing weak C—H···O hydrogen bonds with dashed lines. H-atoms not involved in hydrogen bonding have been excluded.

Methyl 5-(4-acetoxyphenyl)-2-(2-bromobenzylidine)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate top

Crystal data top

C₂₄H₁₉BrN₂O₅S	Z = 2
M_r = 527.38	F(000) = 536
Triclinic, P1	D_x = 1.593 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6018 (5) Å	Cell parameters from 4777 reflections
b = 11.9648 (7) Å	θ = 2.8–27.0°
c = 14.0877 (9) Å	µ = 2.00 mm⁻¹
α = 106.425 (1)°	T = 296 K
β = 104.700 (2)°	Block, yellow
γ = 106.296 (1)°	0.18 × 0.16 × 0.16 mm
V = 1099.75 (12) Å³

Data collection top

Bruker SMART APEX CCD detector diffractometer	4777 independent reflections
Radiation source: fine-focus sealed tube	3989 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −7→9
T_min = 0.714, T_max = 0.740	k = −15→15
9029 measured reflections	l = −17→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0443P)² + 0.7937P] where P = (F_o² + 2F_c²)/3
4777 reflections	(Δ/σ)_max < 0.001
301 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₂₄H₁₉BrN₂O₅S	γ = 106.296 (1)°
M_r = 527.38	V = 1099.75 (12) Å³
Triclinic, P1	Z = 2
a = 7.6018 (5) Å	Mo Kα radiation
b = 11.9648 (7) Å	µ = 2.00 mm⁻¹
c = 14.0877 (9) Å	T = 296 K
α = 106.425 (1)°	0.18 × 0.16 × 0.16 mm
β = 104.700 (2)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	4777 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3989 reflections with I > 2σ(I)
T_min = 0.714, T_max = 0.740	R_int = 0.026
9029 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	Δρ_max = 0.58 e Å⁻³
4777 reflections	Δρ_min = −0.61 e Å⁻³
301 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
C1	0.3032 (4)	0.5765 (2)	0.84902 (18)	0.0216 (5)
H1A	0.4212	0.6045	0.9093	0.032*
H1B	0.2507	0.4862	0.8164	0.032*
H1C	0.2083	0.6040	0.8716	0.032*
C2	0.3542 (3)	0.5692 (2)	0.42420 (17)	0.0137 (4)
C3	0.4784 (3)	0.6889 (2)	0.51728 (17)	0.0135 (4)
C4	0.6434 (4)	0.9217 (2)	1.08072 (18)	0.0294 (6)
H4A	0.7732	0.9210	1.1031	0.044*
H4B	0.5811	0.9043	1.1291	0.044*
H4C	0.6517	1.0030	1.0800	0.044*
C5	0.5037 (3)	0.7934 (2)	0.70450 (16)	0.0125 (4)
H5	0.6450	0.8395	0.7254	0.015*
C6	0.4688 (3)	0.7494 (2)	0.79134 (17)	0.0139 (4)
C7	0.3495 (3)	0.6308 (2)	0.77040 (17)	0.0141 (4)
C8	0.5830 (3)	0.8511 (2)	0.89783 (17)	0.0164 (5)
C9	0.3027 (3)	0.5690 (2)	0.59347 (17)	0.0129 (4)
C10	0.2005 (3)	0.8465 (2)	0.67420 (17)	0.0164 (5)
H10	0.1380	0.7744	0.6844	0.020*
C11	0.3962 (3)	0.8789 (2)	0.68289 (16)	0.0129 (4)
C12	0.4888 (3)	0.9866 (2)	0.66788 (18)	0.0169 (5)
H12	0.6196	1.0090	0.6737	0.020*
C13	0.3871 (4)	1.0614 (2)	0.64419 (18)	0.0196 (5)
H13	0.4489	1.1333	0.6336	0.024*
C14	0.1933 (4)	1.0274 (2)	0.63663 (17)	0.0177 (5)
C15	0.0973 (3)	0.9204 (2)	0.65043 (19)	0.0190 (5)
H15	−0.0339	0.8980	0.6440	0.023*
C16	0.0214 (4)	1.1615 (2)	0.6767 (2)	0.0237 (5)
C17	−0.0856 (4)	1.2323 (2)	0.6298 (2)	0.0259 (6)
H17A	−0.1463	1.2671	0.6763	0.039*
H17B	−0.1848	1.1760	0.5620	0.039*
H17C	0.0057	1.2991	0.6213	0.039*
C18	0.3621 (3)	0.5584 (2)	0.32793 (17)	0.0145 (4)
H18	0.4543	0.6275	0.3266	0.017*
C19	0.2483 (3)	0.4550 (2)	0.22544 (18)	0.0163 (5)
C20	0.1439 (3)	0.3325 (2)	0.21514 (19)	0.0180 (5)
H20	0.1464	0.3160	0.2760	0.022*
C21	0.0370 (4)	0.2353 (2)	0.1167 (2)	0.0244 (5)
H21	−0.0314	0.1550	0.1121	0.029*
C22	0.0323 (4)	0.2580 (3)	0.0253 (2)	0.0322 (6)
H22	−0.0401	0.1931	−0.0408	0.039*
C23	0.1350 (5)	0.3770 (3)	0.0321 (2)	0.0355 (7)
H23	0.1331	0.3922	−0.0293	0.043*
C24	0.2407 (4)	0.4736 (2)	0.13075 (19)	0.0257 (6)
Br1	0.37745 (6)	0.63467 (3)	0.13393 (2)	0.04578 (13)
N1	0.4376 (3)	0.68110 (17)	0.60657 (14)	0.0122 (4)
N2	0.2509 (3)	0.53974 (17)	0.66529 (14)	0.0150 (4)
O1	0.5953 (2)	0.78204 (15)	0.51788 (12)	0.0176 (3)
O2	0.7097 (2)	0.94816 (15)	0.91182 (13)	0.0216 (4)
O3	0.5290 (3)	0.82642 (16)	0.97517 (13)	0.0251 (4)
O4	0.0946 (3)	1.10282 (16)	0.60848 (13)	0.0243 (4)
O5	0.0390 (4)	1.1543 (2)	0.76119 (17)	0.0451 (6)
S1	0.20567 (8)	0.46190 (5)	0.46166 (4)	0.01442 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0278 (13)	0.0208 (12)	0.0168 (11)	0.0060 (10)	0.0100 (10)	0.0095 (9)
C2	0.0122 (11)	0.0147 (10)	0.0162 (10)	0.0067 (9)	0.0051 (9)	0.0073 (9)
C3	0.0142 (11)	0.0164 (11)	0.0136 (10)	0.0087 (9)	0.0055 (8)	0.0076 (9)
C4	0.0452 (17)	0.0241 (13)	0.0095 (11)	0.0075 (12)	0.0061 (11)	0.0022 (10)
C5	0.0119 (10)	0.0130 (10)	0.0105 (9)	0.0036 (8)	0.0030 (8)	0.0036 (8)
C6	0.0152 (11)	0.0178 (11)	0.0109 (10)	0.0093 (9)	0.0047 (8)	0.0055 (9)
C7	0.0158 (11)	0.0173 (11)	0.0124 (10)	0.0081 (9)	0.0065 (9)	0.0070 (9)
C8	0.0202 (12)	0.0189 (11)	0.0129 (10)	0.0118 (10)	0.0047 (9)	0.0067 (9)
C9	0.0119 (10)	0.0137 (10)	0.0130 (10)	0.0062 (9)	0.0031 (8)	0.0051 (8)
C10	0.0162 (11)	0.0138 (10)	0.0167 (11)	0.0028 (9)	0.0054 (9)	0.0057 (9)
C11	0.0150 (11)	0.0131 (10)	0.0081 (9)	0.0044 (9)	0.0032 (8)	0.0021 (8)
C12	0.0165 (11)	0.0170 (11)	0.0180 (11)	0.0059 (9)	0.0087 (9)	0.0061 (9)
C13	0.0283 (13)	0.0149 (11)	0.0195 (11)	0.0085 (10)	0.0119 (10)	0.0090 (9)
C14	0.0257 (13)	0.0187 (11)	0.0119 (10)	0.0139 (10)	0.0058 (9)	0.0055 (9)
C15	0.0138 (11)	0.0199 (11)	0.0216 (11)	0.0062 (9)	0.0040 (9)	0.0079 (9)
C16	0.0229 (13)	0.0229 (12)	0.0249 (13)	0.0114 (11)	0.0065 (10)	0.0075 (10)
C17	0.0267 (14)	0.0229 (13)	0.0294 (13)	0.0148 (11)	0.0075 (11)	0.0085 (11)
C18	0.0148 (11)	0.0145 (10)	0.0152 (10)	0.0067 (9)	0.0055 (9)	0.0058 (9)
C19	0.0153 (11)	0.0206 (11)	0.0150 (10)	0.0100 (10)	0.0059 (9)	0.0061 (9)
C20	0.0148 (11)	0.0212 (12)	0.0186 (11)	0.0080 (10)	0.0076 (9)	0.0060 (9)
C21	0.0181 (12)	0.0206 (12)	0.0249 (13)	0.0029 (10)	0.0067 (10)	0.0005 (10)
C22	0.0327 (15)	0.0285 (14)	0.0182 (12)	0.0047 (12)	0.0028 (11)	−0.0027 (11)
C23	0.0506 (18)	0.0353 (16)	0.0148 (12)	0.0130 (14)	0.0091 (12)	0.0072 (11)
C24	0.0346 (15)	0.0217 (12)	0.0172 (12)	0.0082 (11)	0.0081 (11)	0.0059 (10)
Br1	0.0837 (3)	0.02598 (16)	0.01761 (15)	0.00523 (15)	0.01693 (15)	0.01100 (11)
N1	0.0133 (9)	0.0127 (9)	0.0109 (8)	0.0053 (7)	0.0046 (7)	0.0046 (7)
N2	0.0154 (9)	0.0158 (9)	0.0133 (9)	0.0043 (8)	0.0053 (7)	0.0063 (7)
O1	0.0202 (8)	0.0156 (8)	0.0158 (8)	0.0038 (7)	0.0076 (7)	0.0063 (6)
O2	0.0247 (9)	0.0173 (8)	0.0163 (8)	0.0032 (7)	0.0052 (7)	0.0041 (7)
O3	0.0368 (11)	0.0193 (8)	0.0110 (8)	0.0030 (8)	0.0080 (7)	0.0027 (7)
O4	0.0357 (10)	0.0278 (9)	0.0220 (9)	0.0226 (8)	0.0133 (8)	0.0143 (7)
O5	0.0676 (16)	0.0675 (16)	0.0336 (11)	0.0522 (14)	0.0300 (11)	0.0293 (11)
S1	0.0143 (3)	0.0142 (3)	0.0112 (2)	0.0025 (2)	0.0034 (2)	0.0038 (2)

Geometric parameters (Å, º) top

C1—C7	1.500 (3)	C11—C12	1.385 (3)
C1—H1A	0.9600	C12—C13	1.391 (3)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—C14	1.381 (4)
C2—C18	1.344 (3)	C13—H13	0.9300
C2—C3	1.487 (3)	C14—C15	1.378 (3)
C2—S1	1.754 (2)	C14—O4	1.402 (3)
C3—O1	1.211 (3)	C15—H15	0.9300
C3—N1	1.391 (3)	C16—O5	1.195 (3)
C4—O3	1.448 (3)	C16—O4	1.354 (3)
C4—H4A	0.9600	C16—C17	1.497 (3)
C4—H4B	0.9600	C17—H17A	0.9600
C4—H4C	0.9600	C17—H17B	0.9600
C5—N1	1.478 (3)	C17—H17C	0.9600
C5—C6	1.515 (3)	C18—C19	1.456 (3)
C5—C11	1.525 (3)	C18—H18	0.9300
C5—H5	0.9800	C19—C24	1.403 (3)
C6—C7	1.352 (3)	C19—C20	1.403 (3)
C6—C8	1.483 (3)	C20—C21	1.387 (3)
C7—N2	1.417 (3)	C20—H20	0.9300
C8—O2	1.209 (3)	C21—C22	1.382 (4)
C8—O3	1.335 (3)	C21—H21	0.9300
C9—N2	1.275 (3)	C22—C23	1.381 (4)
C9—N1	1.370 (3)	C22—H22	0.9300
C9—S1	1.750 (2)	C23—C24	1.384 (4)
C10—C15	1.391 (3)	C23—H23	0.9300
C10—C11	1.391 (3)	C24—Br1	1.898 (3)
C10—H10	0.9300

C7—C1—H1A	109.5	C14—C13—H13	120.4
C7—C1—H1B	109.5	C12—C13—H13	120.4
H1A—C1—H1B	109.5	C15—C14—C13	121.7 (2)
C7—C1—H1C	109.5	C15—C14—O4	121.2 (2)
H1A—C1—H1C	109.5	C13—C14—O4	117.1 (2)
H1B—C1—H1C	109.5	C14—C15—C10	118.7 (2)
C18—C2—C3	119.9 (2)	C14—C15—H15	120.7
C18—C2—S1	129.72 (18)	C10—C15—H15	120.7
C3—C2—S1	110.36 (16)	O5—C16—O4	123.4 (2)
O1—C3—N1	123.4 (2)	O5—C16—C17	126.0 (2)
O1—C3—C2	126.8 (2)	O4—C16—C17	110.6 (2)
N1—C3—C2	109.76 (19)	C16—C17—H17A	109.5
O3—C4—H4A	109.5	C16—C17—H17B	109.5
O3—C4—H4B	109.5	H17A—C17—H17B	109.5
H4A—C4—H4B	109.5	C16—C17—H17C	109.5
O3—C4—H4C	109.5	H17A—C17—H17C	109.5
H4A—C4—H4C	109.5	H17B—C17—H17C	109.5
H4B—C4—H4C	109.5	C2—C18—C19	129.8 (2)
N1—C5—C6	108.19 (17)	C2—C18—H18	115.1
N1—C5—C11	109.45 (16)	C19—C18—H18	115.1
C6—C5—C11	113.06 (18)	C24—C19—C20	116.4 (2)
N1—C5—H5	108.7	C24—C19—C18	120.8 (2)
C6—C5—H5	108.7	C20—C19—C18	122.8 (2)
C11—C5—H5	108.7	C21—C20—C19	121.8 (2)
C7—C6—C8	126.3 (2)	C21—C20—H20	119.1
C7—C6—C5	122.34 (19)	C19—C20—H20	119.1
C8—C6—C5	111.35 (19)	C22—C21—C20	119.9 (2)
C6—C7—N2	121.6 (2)	C22—C21—H21	120.1
C6—C7—C1	127.3 (2)	C20—C21—H21	120.1
N2—C7—C1	111.08 (19)	C23—C22—C21	120.1 (2)
O2—C8—O3	123.7 (2)	C23—C22—H22	119.9
O2—C8—C6	122.5 (2)	C21—C22—H22	119.9
O3—C8—C6	113.8 (2)	C22—C23—C24	119.6 (3)
N2—C9—N1	126.87 (19)	C22—C23—H23	120.2
N2—C9—S1	121.52 (17)	C24—C23—H23	120.2
N1—C9—S1	111.59 (16)	C23—C24—C19	122.2 (2)
C15—C10—C11	120.8 (2)	C23—C24—Br1	117.3 (2)
C15—C10—H10	119.6	C19—C24—Br1	120.52 (18)
C11—C10—H10	119.6	C9—N1—C3	116.59 (18)
C12—C11—C10	119.3 (2)	C9—N1—C5	120.26 (18)
C12—C11—C5	120.8 (2)	C3—N1—C5	122.05 (18)
C10—C11—C5	119.8 (2)	C9—N2—C7	116.48 (19)
C11—C12—C13	120.4 (2)	C8—O3—C4	115.0 (2)
C11—C12—H12	119.8	C16—O4—C14	118.97 (19)
C13—C12—H12	119.8	C9—S1—C2	91.67 (11)
C14—C13—C12	119.1 (2)

C18—C2—C3—O1	−1.9 (4)	C19—C20—C21—C22	0.3 (4)
S1—C2—C3—O1	−179.35 (19)	C20—C21—C22—C23	0.5 (4)
C18—C2—C3—N1	176.6 (2)	C21—C22—C23—C24	−0.7 (5)
S1—C2—C3—N1	−0.9 (2)	C22—C23—C24—C19	0.2 (5)
N1—C5—C6—C7	−16.1 (3)	C22—C23—C24—Br1	−179.8 (2)
C11—C5—C6—C7	105.3 (2)	C20—C19—C24—C23	0.5 (4)
N1—C5—C6—C8	162.92 (17)	C18—C19—C24—C23	179.5 (3)
C11—C5—C6—C8	−75.7 (2)	C20—C19—C24—Br1	−179.49 (17)
C8—C6—C7—N2	−178.3 (2)	C18—C19—C24—Br1	−0.4 (3)
C5—C6—C7—N2	0.6 (3)	N2—C9—N1—C3	176.5 (2)
C8—C6—C7—C1	1.2 (4)	S1—C9—N1—C3	−2.1 (2)
C5—C6—C7—C1	−179.9 (2)	N2—C9—N1—C5	−15.3 (3)
C7—C6—C8—O2	168.1 (2)	S1—C9—N1—C5	166.10 (15)
C5—C6—C8—O2	−10.9 (3)	O1—C3—N1—C9	−179.5 (2)
C7—C6—C8—O3	−13.6 (3)	C2—C3—N1—C9	2.0 (3)
C5—C6—C8—O3	167.38 (18)	O1—C3—N1—C5	12.5 (3)
C15—C10—C11—C12	0.2 (3)	C2—C3—N1—C5	−166.05 (18)
C15—C10—C11—C5	−177.5 (2)	C6—C5—N1—C9	22.8 (3)
N1—C5—C11—C12	−102.4 (2)	C11—C5—N1—C9	−100.8 (2)
C6—C5—C11—C12	137.0 (2)	C6—C5—N1—C3	−169.64 (18)
N1—C5—C11—C10	75.3 (2)	C11—C5—N1—C3	66.8 (2)
C6—C5—C11—C10	−45.4 (3)	N1—C9—N2—C7	−2.9 (3)
C10—C11—C12—C13	−0.1 (3)	S1—C9—N2—C7	175.63 (15)
C5—C11—C12—C13	177.53 (19)	C6—C7—N2—C9	10.2 (3)
C11—C12—C13—C14	0.5 (3)	C1—C7—N2—C9	−169.4 (2)
C12—C13—C14—C15	−1.0 (3)	O2—C8—O3—C4	−4.2 (3)
C12—C13—C14—O4	−177.54 (19)	C6—C8—O3—C4	177.6 (2)
C13—C14—C15—C10	1.0 (3)	O5—C16—O4—C14	1.3 (4)
O4—C14—C15—C10	177.5 (2)	C17—C16—O4—C14	−177.5 (2)
C11—C10—C15—C14	−0.6 (3)	C15—C14—O4—C16	63.7 (3)
C3—C2—C18—C19	−176.1 (2)	C13—C14—O4—C16	−119.7 (2)
S1—C2—C18—C19	0.8 (4)	N2—C9—S1—C2	−177.4 (2)
C2—C18—C19—C24	163.0 (2)	N1—C9—S1—C2	1.26 (17)
C2—C18—C19—C20	−18.0 (4)	C18—C2—S1—C9	−177.3 (2)
C24—C19—C20—C21	−0.7 (3)	C3—C2—S1—C9	−0.18 (16)
C18—C19—C20—C21	−179.7 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C5–C7/C9/N1/N2 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.93	2.60	3.343 (4)	138
C10—H10···Cgⁱⁱ	0.93	2.61	3.513 (4)	147

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x−1, −y−1, −z−1.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C5–C7/C9/N1/N2 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.930	2.60	3.343 (4)	138
C10—H10···Cgⁱⁱ	0.930	2.61	3.513 (4)	147

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x−1, −y−1, −z−1.

Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance.

References

Alam, O., Khan, S. A., Siddiqui, N. & Ahsan, W. (2010). Med. Chem. Res. 19, 1245–1258. Web of Science CrossRef CAS Google Scholar
Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A. & O'Reilly, B. C. (1991). J. Med. Chem. 34, 806–811. CrossRef PubMed CAS Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. 34, 1555–1573. CrossRef CAS Google Scholar
Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043–1052. Web of Science CrossRef PubMed CAS Google Scholar
Nagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nagarajaiah, H., Fathima, N. & Begum, N. S. (2012). Acta Cryst. E68, o1257–o1258. CSD CrossRef CAS IUCr Journals Google Scholar
Rovnyak, G. C., Atwal, K. S., Hedberg, A., Kimball, S. D., Moreland, S., Gougoutas, J. Z., O'Reilly, B. C., Schwartz, J. & Malley, M. F. (1992). J. Med. Chem. 35, 3254–3263. CSD CrossRef PubMed CAS Web of Science 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1262

doi:10.1107/S1600536813019132

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Methyl 5-(4-acet­­oxy­phen­yl)-2-(2-bromo­benzyl­idine)-7-methyl-3-oxo-2,3-di­hydro-5H-1,3-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 5-(4-acetoxyphenyl)-2-(2-bromobenzylidine)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate