Crystal structure of ethyl 2-(2-fluoro­benzyl­idene)-5-(4-fluoro­phen­yl)-7-methyl-3-oxo-2,3-di­hydro-5H-1,3-thia­zolo[3,2-a]pyrimidine-6-carb­oxy­late

Krishnamurthy, M.S.; Begum, N.S.

doi:10.1107/S1600536814025008

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages o1270-o1271

doi:10.1107/S1600536814025008

Open

access

Crystal structure of ethyl 2-(2-fluorobenzylidene)-5-(4-fluorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate

M. S. Krishnamurthy ^a and Noor Shahina Begum ^a ^*

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

Edited by A. J. Lough, University of Toronto, Canada (Received 26 October 2014; accepted 14 November 2014; online 19 November 2014)

In the title molecule, C₂₃H₁₈F₂N₂O₃S, the 4-fluoro-substituted and 2-fluoro-substituted benzene rings form dihedral angles of 88.16 (8) and 23.1 (1)°, respectively, with the thiazole ring. The pyrimidine ring adopts a flattened sofa conformation with the sp³-hydridized C atom forming the flap. In the crystal, pairs of weak C—H⋯O hydrogen bonds link molecules related by twofold rotation axes, forming R²₂(10) rings, which are in turn linked by weak C—H⋯N interactions to form chains of rings along [010]. In addition, weak C—H⋯π(arene) interactions link the chains into layers parallel to (001) and π–π interactions with a centroid–centroid distance of 3.836 (10) Å connect these layers into a three-dimensional network.

Keywords: crystal structure; fused pyrimidine derivative; fluoro-substituted compound; hydrogen bonding; C—H⋯π interactions; π–π interactions.

CCDC reference: 1034132

1. Related literature

For the biological activity of fused pyrimidine derivatives, see: Alam et al. (2010a ,b ); Jotani et al. (2009 ). For the biological activity of fluoro-substituted compounds, see: Guru Row (1999 ); Yamazaki et al. (2009 ). For related structures, see: Krishnamurthy et al. (2014 ); Nagarajaiah & Begum (2011 ). For hydrogen-bond graph-set motifs motifs, see: Bernstein et al. (1995 ).

2. Experimental

2.1. Crystal data

C₂₃H₁₈F₂N₂O₃S
M_r = 440.45
Monoclinic, C 2/c
a = 24.746 (5) Å
b = 9.6879 (17) Å
c = 16.757 (3) Å
β = 92.022 (5)°
V = 4014.7 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.18 × 0.16 × 0.16 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.963, T_max = 0.967
9957 measured reflections
3520 independent reflections
3169 reflections with I > 2σ(I)
R_int = 0.034

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.03
3520 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2ⁱ	0.99	2.48	3.119 (2)	122
C15—H15⋯N2ⁱⁱ	0.95	2.57	3.488 (2)	162
C8—H8B⋯Cgⁱⁱⁱ	0.99	2.96	3.911 (2)	162
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) x, y+1, z; (iii) $[-x+{\script{3\over 2}}, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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 DIAMOND (Brandenburg & Berndt, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1034132

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814025008/lh5738sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814025008/lh5738Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814025008/lh5738Isup3.cml

checkCIF report

Comment top

A heterocyclic nucleus imparts an important role in medicinal chemistry and serves as a key template for the development of various therapeutic agents. Among the various heterocyclic compounds, the synthetic studies of the fused pyrimidines that is specifically the thiazolo [3,2-a]pyrimidines have been reported extensively because of their structural diversity and association with a wide spectrum of biological activities such as antiviral, anticancer, anti-inflammatory and anti-hypertensive properties (Alam et al., 2010a,b; Jotani et al., 2009). The presence of a fluorine atom in the molecule can have profound and unexpected results on the biological activity of the compound (Guru Row, 1999; Yamazaki et al., 2009). Herein, we report the crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1. The 4-fluoro-substituted (C11–C16) and 2-fluoro-substituted (C18–C23) benzene rings form dihedral angles of 88.16 (8)° and 23.1 (1)°, respectively with the thiazole ring (C2/C3/N1/C9/S1). The pyrimidine ring adopts a flattened sofa conformation with atom C5 forming the flap. The carbonyl group of the exocyclic ester at C6 adopts a cis orientation with respect to C6═C7 double bond. The bond lengths and angles are in good agreement with those reported previously for related structures (Krishnamurthy et al., 2014; Nagarajaiah & Begum et al., 2011). In the crystal, pairs of weak C—H···O hydrogen bonds link molecules related by twofold rotation axes to form R²₂(10) rings (Bernstein et al., 1995), which are in turn linked by weak C—H···N interactions to form chains of rings (Fig. 2) along [010]. In addition, weak C—H···π(arene) interaction link chains into layers parallel to (001) and π···π interactions with a centroid–centroid distance of 3.836 (10)Å connect these layers into a three-dimensional network. The π···π interactions occur between symmetry related Cg–Cg(1-x, y, 3/2-z) rings, where Cg is the centroid of the C11–C16 ring.

Related literature top

For the biological activity of fused pyrimidine derivatives, see: Alam et al. (2010a,b); Jotani et al. (2009). For the biological activity of fluoro-substituted compounds, see: Guru Row (1999); Yamazaki et al. (2009). For related structures, see: Krishnamurthy et al. (2014); Nagarajaiah & Begum (2011). For hydrogen-bond graph-set motifs motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 4-(4-fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro- pyrimidine-5-carboxylic acid ethyl ester (10 mmol), chloroaceticacid (10 mmol), 2-fluorobenzaldehyde (10 mmol) and sodium acetate (1.5 g) was placed in a mixture of glacial acetic acid and acetic anhydride (25 ml; 1:1) and refluxed for 8—10 h until the TLC assay indicated that the reaction was complete. The reaction mixture was concentrated and the solid thus obtained was filtered and recrystallized from ethyl acetate to get the title compound (82% yield, mp 444 K). The compound was recrystallized by slow evaporation from dimethylformamide (DMF) solvent, yielding pale yellow single crystals suitable for X-ray diffraction studies.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (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 DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. The molecular structure of the title compound drawn with 50% probability level ellipsoids. H atoms are presented as small spheres of arbitrary radius.

Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines. For clarity H atoms not involved in hydrogen bonding are not shown.

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

Crystal data top

C₂₃H₁₈F₂N₂O₃S	F(000) = 1824
M_r = 440.45	D_x = 1.457 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3520 reflections
a = 24.746 (5) Å	θ = 1.7–25.0°
b = 9.6879 (17) Å	µ = 0.21 mm⁻¹
c = 16.757 (3) Å	T = 100 K
β = 92.022 (5)°	Block, yellow
V = 4014.7 (13) Å³	0.18 × 0.16 × 0.16 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	3520 independent reflections
Radiation source: fine-focus sealed tube	3169 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −29→29
T_min = 0.963, T_max = 0.967	k = −11→11
9957 measured reflections	l = −16→19

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0629P)² + 4.1702P] where P = (F_o² + 2F_c²)/3
3520 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₃H₁₈F₂N₂O₃S	V = 4014.7 (13) Å³
M_r = 440.45	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.746 (5) Å	µ = 0.21 mm⁻¹
b = 9.6879 (17) Å	T = 100 K
c = 16.757 (3) Å	0.18 × 0.16 × 0.16 mm
β = 92.022 (5)°

Data collection top

Bruker SMART APEX CCD diffractometer	3520 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3169 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.967	R_int = 0.034
9957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
3520 reflections	Δρ_min = −0.34 e Å⁻³
282 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	0.565115 (17)	0.43828 (4)	0.65490 (3)	0.02504 (15)
F1	0.43031 (4)	1.13600 (11)	0.77686 (7)	0.0351 (3)
O3	0.36126 (5)	0.76825 (13)	0.48959 (7)	0.0266 (3)
O1	0.56122 (5)	0.78762 (12)	0.54420 (7)	0.0244 (3)
N1	0.50281 (5)	0.61793 (14)	0.58253 (8)	0.0194 (3)
N2	0.45904 (6)	0.41667 (14)	0.62854 (9)	0.0238 (3)
F2	0.75173 (5)	0.66324 (14)	0.56697 (9)	0.0542 (4)
C6	0.40531 (7)	0.59402 (17)	0.56217 (10)	0.0201 (4)
O2	0.30987 (5)	0.59424 (14)	0.53122 (10)	0.0430 (4)
C5	0.45256 (6)	0.69513 (16)	0.56176 (10)	0.0196 (4)
H5	0.4553	0.7335	0.5067	0.023*
C3	0.55343 (7)	0.67752 (17)	0.57664 (9)	0.0200 (4)
C10	0.35362 (7)	0.64859 (18)	0.52739 (11)	0.0245 (4)
C15	0.44806 (7)	1.05927 (17)	0.64716 (11)	0.0257 (4)
H15	0.4531	1.1518	0.6302	0.031*
C2	0.59521 (7)	0.58692 (18)	0.61561 (10)	0.0227 (4)
C11	0.44590 (6)	0.81437 (17)	0.61988 (10)	0.0197 (4)
C17	0.64788 (7)	0.62041 (19)	0.61580 (10)	0.0254 (4)
H17	0.6564	0.7051	0.5906	0.031*
C7	0.40961 (7)	0.46736 (17)	0.59525 (10)	0.0221 (4)
C16	0.45294 (6)	0.94976 (17)	0.59459 (11)	0.0228 (4)
H16	0.4612	0.9674	0.5406	0.027*
C9	0.50089 (7)	0.49166 (17)	0.61977 (10)	0.0214 (4)
C12	0.43361 (6)	0.78875 (17)	0.69901 (10)	0.0210 (4)
H12	0.4287	0.6964	0.7165	0.025*
C13	0.42838 (7)	0.89693 (18)	0.75269 (10)	0.0236 (4)
H13	0.4201	0.8801	0.8068	0.028*
C14	0.43566 (7)	1.02957 (18)	0.72492 (11)	0.0250 (4)
C1	0.36551 (7)	0.36219 (19)	0.60085 (11)	0.0292 (4)
H1A	0.3303	0.4078	0.5942	0.044*
H1B	0.3681	0.3171	0.6532	0.044*
H1C	0.3692	0.2929	0.5588	0.044*
C18	0.69365 (7)	0.5428 (2)	0.64997 (11)	0.0285 (4)
C8	0.31251 (7)	0.8348 (2)	0.45669 (12)	0.0315 (4)
H8A	0.2865	0.8508	0.4993	0.038*
H8B	0.2950	0.7755	0.4152	0.038*
C19	0.74540 (7)	0.5658 (2)	0.62342 (11)	0.0299 (4)
C20	0.79025 (8)	0.4941 (2)	0.65104 (12)	0.0368 (5)
H20	0.8249	0.5135	0.6311	0.044*
C21	0.78402 (8)	0.3936 (3)	0.70814 (13)	0.0425 (5)
H21	0.8143	0.3413	0.7271	0.051*
C4	0.32924 (9)	0.9693 (2)	0.42117 (15)	0.0472 (6)
H4A	0.3483	1.0250	0.4621	0.071*
H4B	0.2971	1.0192	0.4011	0.071*
H4C	0.3533	0.9519	0.3771	0.071*
C22	0.73389 (9)	0.3693 (3)	0.73753 (16)	0.0636 (8)
H22	0.7296	0.3010	0.7775	0.076*
C23	0.68945 (9)	0.4436 (3)	0.70917 (14)	0.0552 (7)
H23	0.6551	0.4263	0.7308	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0253 (3)	0.0241 (3)	0.0257 (3)	0.00599 (16)	0.00118 (18)	0.00482 (17)
F1	0.0385 (6)	0.0243 (6)	0.0427 (7)	0.0029 (5)	0.0040 (5)	−0.0127 (5)
O3	0.0179 (6)	0.0298 (7)	0.0321 (7)	0.0029 (5)	0.0001 (5)	0.0065 (5)
O1	0.0208 (6)	0.0234 (6)	0.0292 (7)	0.0007 (5)	0.0034 (5)	0.0021 (5)
N1	0.0193 (7)	0.0177 (7)	0.0214 (7)	0.0029 (5)	0.0020 (6)	0.0010 (6)
N2	0.0266 (8)	0.0207 (7)	0.0243 (8)	0.0006 (6)	0.0026 (6)	0.0014 (6)
F2	0.0245 (6)	0.0584 (8)	0.0795 (10)	−0.0091 (6)	−0.0015 (6)	0.0307 (7)
C6	0.0198 (8)	0.0212 (8)	0.0195 (8)	−0.0013 (7)	0.0029 (6)	−0.0030 (7)
O2	0.0199 (7)	0.0314 (7)	0.0774 (11)	−0.0033 (6)	−0.0031 (7)	0.0116 (7)
C5	0.0171 (8)	0.0194 (8)	0.0221 (8)	0.0026 (6)	0.0005 (6)	0.0022 (7)
C3	0.0209 (8)	0.0214 (8)	0.0180 (8)	0.0017 (7)	0.0033 (6)	−0.0018 (7)
C10	0.0217 (9)	0.0222 (8)	0.0298 (9)	−0.0001 (7)	0.0032 (7)	−0.0030 (7)
C15	0.0207 (9)	0.0168 (8)	0.0399 (11)	0.0003 (6)	0.0035 (8)	0.0025 (7)
C2	0.0243 (9)	0.0264 (9)	0.0176 (8)	0.0055 (7)	0.0023 (7)	−0.0019 (7)
C11	0.0136 (7)	0.0204 (8)	0.0251 (9)	0.0011 (6)	0.0000 (6)	0.0001 (7)
C17	0.0239 (9)	0.0308 (9)	0.0217 (9)	0.0036 (7)	0.0014 (7)	−0.0013 (7)
C7	0.0233 (9)	0.0227 (8)	0.0206 (8)	−0.0002 (7)	0.0049 (7)	−0.0033 (7)
C16	0.0183 (8)	0.0228 (9)	0.0274 (9)	0.0012 (6)	0.0026 (7)	0.0030 (7)
C9	0.0257 (9)	0.0202 (8)	0.0186 (8)	0.0043 (7)	0.0026 (7)	−0.0011 (7)
C12	0.0181 (8)	0.0177 (8)	0.0271 (9)	0.0007 (6)	0.0005 (7)	0.0032 (7)
C13	0.0196 (8)	0.0265 (9)	0.0248 (9)	0.0028 (7)	0.0009 (7)	−0.0009 (7)
C14	0.0186 (8)	0.0215 (8)	0.0349 (10)	0.0028 (7)	0.0002 (7)	−0.0081 (7)
C1	0.0291 (10)	0.0265 (9)	0.0322 (10)	−0.0059 (8)	0.0049 (8)	0.0019 (8)
C18	0.0211 (9)	0.0402 (10)	0.0241 (9)	0.0053 (8)	−0.0003 (7)	−0.0038 (8)
C8	0.0185 (9)	0.0344 (10)	0.0412 (11)	0.0042 (7)	−0.0049 (8)	0.0055 (9)
C19	0.0240 (9)	0.0342 (10)	0.0312 (10)	−0.0031 (8)	−0.0018 (7)	0.0000 (8)
C20	0.0177 (9)	0.0523 (13)	0.0402 (11)	−0.0006 (8)	−0.0014 (8)	−0.0022 (10)
C21	0.0252 (10)	0.0627 (14)	0.0392 (12)	0.0123 (10)	−0.0038 (9)	0.0083 (11)
C4	0.0290 (11)	0.0514 (13)	0.0612 (15)	0.0061 (9)	0.0010 (10)	0.0276 (12)
C22	0.0288 (12)	0.102 (2)	0.0601 (16)	0.0125 (13)	0.0013 (11)	0.0483 (16)
C23	0.0227 (11)	0.094 (2)	0.0489 (14)	0.0123 (11)	0.0073 (9)	0.0370 (14)

Geometric parameters (Å, º) top

S1—C9	1.7532 (17)	C17—H17	0.9500
S1—C2	1.7596 (18)	C7—C1	1.498 (2)
F1—C14	1.359 (2)	C16—H16	0.9500
O3—C10	1.338 (2)	C12—C13	1.390 (2)
O3—C8	1.459 (2)	C12—H12	0.9500
O1—C3	1.216 (2)	C13—C14	1.381 (3)
N1—C9	1.375 (2)	C13—H13	0.9500
N1—C3	1.386 (2)	C1—H1A	0.9800
N1—C5	1.482 (2)	C1—H1B	0.9800
N2—C9	1.278 (2)	C1—H1C	0.9800
N2—C7	1.414 (2)	C18—C23	1.387 (3)
F2—C19	1.349 (2)	C18—C19	1.389 (3)
C6—C7	1.349 (2)	C8—C4	1.497 (3)
C6—C10	1.484 (2)	C8—H8A	0.9900
C6—C5	1.526 (2)	C8—H8B	0.9900
O2—C10	1.208 (2)	C19—C20	1.376 (3)
C5—C11	1.524 (2)	C20—C21	1.378 (3)
C5—H5	1.0000	C20—H20	0.9500
C3—C2	1.489 (2)	C21—C22	1.371 (3)
C15—C14	1.380 (3)	C21—H21	0.9500
C15—C16	1.387 (2)	C4—H4A	0.9800
C15—H15	0.9500	C4—H4B	0.9800
C2—C17	1.343 (3)	C4—H4C	0.9800
C11—C16	1.391 (2)	C22—C23	1.385 (3)
C11—C12	1.393 (2)	C22—H22	0.9500
C17—C18	1.460 (2)	C23—H23	0.9500

C9—S1—C2	91.35 (8)	C11—C12—H12	119.7
C10—O3—C8	115.66 (13)	C14—C13—C12	117.86 (16)
C9—N1—C3	116.66 (14)	C14—C13—H13	121.1
C9—N1—C5	120.90 (13)	C12—C13—H13	121.1
C3—N1—C5	121.74 (13)	F1—C14—C15	118.47 (16)
C9—N2—C7	116.77 (14)	F1—C14—C13	118.26 (16)
C7—C6—C10	122.66 (15)	C15—C14—C13	123.26 (16)
C7—C6—C5	122.46 (15)	C7—C1—H1A	109.5
C10—C6—C5	114.81 (14)	C7—C1—H1B	109.5
N1—C5—C11	109.96 (13)	H1A—C1—H1B	109.5
N1—C5—C6	108.16 (13)	C7—C1—H1C	109.5
C11—C5—C6	112.57 (13)	H1A—C1—H1C	109.5
N1—C5—H5	108.7	H1B—C1—H1C	109.5
C11—C5—H5	108.7	C23—C18—C19	115.70 (17)
C6—C5—H5	108.7	C23—C18—C17	124.10 (17)
O1—C3—N1	123.73 (15)	C19—C18—C17	120.21 (17)
O1—C3—C2	126.49 (15)	O3—C8—C4	107.36 (15)
N1—C3—C2	109.78 (14)	O3—C8—H8A	110.2
O2—C10—O3	123.02 (16)	C4—C8—H8A	110.2
O2—C10—C6	125.85 (17)	O3—C8—H8B	110.2
O3—C10—C6	111.13 (14)	C4—C8—H8B	110.2
C14—C15—C16	117.88 (16)	H8A—C8—H8B	108.5
C14—C15—H15	121.1	F2—C19—C20	118.49 (17)
C16—C15—H15	121.1	F2—C19—C18	117.92 (16)
C17—C2—C3	121.14 (16)	C20—C19—C18	123.58 (19)
C17—C2—S1	128.34 (14)	C19—C20—C21	118.82 (18)
C3—C2—S1	110.49 (12)	C19—C20—H20	120.6
C16—C11—C12	119.46 (16)	C21—C20—H20	120.6
C16—C11—C5	120.17 (15)	C22—C21—C20	119.71 (19)
C12—C11—C5	120.36 (14)	C22—C21—H21	120.1
C2—C17—C18	128.02 (18)	C20—C21—H21	120.1
C2—C17—H17	116.0	C8—C4—H4A	109.5
C18—C17—H17	116.0	C8—C4—H4B	109.5
C6—C7—N2	122.16 (15)	H4A—C4—H4B	109.5
C6—C7—C1	126.68 (16)	C8—C4—H4C	109.5
N2—C7—C1	111.15 (15)	H4A—C4—H4C	109.5
C15—C16—C11	120.87 (16)	H4B—C4—H4C	109.5
C15—C16—H16	119.6	C21—C22—C23	120.3 (2)
C11—C16—H16	119.6	C21—C22—H22	119.8
N2—C9—N1	126.81 (15)	C23—C22—H22	119.8
N2—C9—S1	121.49 (13)	C22—C23—C18	121.8 (2)
N1—C9—S1	111.69 (12)	C22—C23—H23	119.1
C13—C12—C11	120.67 (15)	C18—C23—H23	119.1
C13—C12—H12	119.7

C9—N1—C5—C11	104.58 (16)	C9—N2—C7—C6	−5.9 (2)
C3—N1—C5—C11	−65.51 (19)	C9—N2—C7—C1	172.94 (15)
C9—N1—C5—C6	−18.7 (2)	C14—C15—C16—C11	−0.5 (2)
C3—N1—C5—C6	171.21 (14)	C12—C11—C16—C15	0.2 (2)
C7—C6—C5—N1	14.5 (2)	C5—C11—C16—C15	−178.72 (15)
C10—C6—C5—N1	−168.64 (13)	C7—N2—C9—N1	1.3 (2)
C7—C6—C5—C11	−107.15 (18)	C7—N2—C9—S1	−177.66 (12)
C10—C6—C5—C11	69.67 (18)	C3—N1—C9—N2	−176.87 (16)
C9—N1—C3—O1	178.82 (15)	C5—N1—C9—N2	12.6 (3)
C5—N1—C3—O1	−10.7 (2)	C3—N1—C9—S1	2.14 (18)
C9—N1—C3—C2	−1.3 (2)	C5—N1—C9—S1	−168.43 (11)
C5—N1—C3—C2	169.20 (13)	C2—S1—C9—N2	177.27 (15)
C8—O3—C10—O2	3.5 (3)	C2—S1—C9—N1	−1.80 (12)
C8—O3—C10—C6	−176.91 (14)	C16—C11—C12—C13	−0.1 (2)
C7—C6—C10—O2	7.4 (3)	C5—C11—C12—C13	178.90 (14)
C5—C6—C10—O2	−169.38 (18)	C11—C12—C13—C14	0.1 (2)
C7—C6—C10—O3	−172.13 (15)	C16—C15—C14—F1	−179.44 (14)
C5—C6—C10—O3	11.1 (2)	C16—C15—C14—C13	0.5 (3)
O1—C3—C2—C17	−2.0 (3)	C12—C13—C14—F1	179.61 (14)
N1—C3—C2—C17	178.08 (15)	C12—C13—C14—C15	−0.4 (3)
O1—C3—C2—S1	179.75 (14)	C2—C17—C18—C23	−21.2 (3)
N1—C3—C2—S1	−0.14 (17)	C2—C17—C18—C19	158.67 (19)
C9—S1—C2—C17	−176.98 (17)	C10—O3—C8—C4	177.01 (17)
C9—S1—C2—C3	1.09 (12)	C23—C18—C19—F2	−178.7 (2)
N1—C5—C11—C16	108.87 (17)	C17—C18—C19—F2	1.4 (3)
C6—C5—C11—C16	−130.46 (16)	C23—C18—C19—C20	1.8 (3)
N1—C5—C11—C12	−70.07 (18)	C17—C18—C19—C20	−178.07 (18)
C6—C5—C11—C12	50.6 (2)	F2—C19—C20—C21	−179.40 (19)
C3—C2—C17—C18	−179.02 (16)	C18—C19—C20—C21	0.0 (3)
S1—C2—C17—C18	−1.1 (3)	C19—C20—C21—C22	−1.5 (4)
C10—C6—C7—N2	−179.71 (15)	C20—C21—C22—C23	1.0 (4)
C5—C6—C7—N2	−3.1 (2)	C21—C22—C23—C18	1.0 (5)
C10—C6—C7—C1	1.6 (3)	C19—C18—C23—C22	−2.3 (4)
C5—C6—C7—C1	178.17 (16)	C17—C18—C23—C22	177.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2ⁱ	0.99	2.48	3.119 (2)	122
C15—H15···N2ⁱⁱ	0.95	2.57	3.488 (2)	162
C8—H8B···Cgⁱⁱⁱ	0.99	2.96	3.911 (2)	162

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, y+1, z; (iii) −x+3/2, y+3/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2ⁱ	0.99	2.48	3.119 (2)	122
C15—H15···N2ⁱⁱ	0.95	2.57	3.488 (2)	162
C8—H8B···Cgⁱⁱⁱ	0.99	2.96	3.911 (2)	162

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, y+1, z; (iii) −x+3/2, y+3/2, −z+3/2.

Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance. MSK thanks the UGC for the UGC–BSR for a meritorious fellowship.

References

Alam, O., Khan, S. A., Siddiqui, N. & Ahsan, W. (2010a). Med. Chem. Res. 19, 1245–1258. Web of Science CrossRef CAS Google Scholar
Alam, O., Khan, S. A., Siddiqui, N., Ahsan, W., Verma, S. P. & Gilani, S. J. (2010b). Eur. J. Med. Chem. 45, 5113—5119. 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
Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker. (1998). SMART, SAINT and SADABS. Bruker Axs Inc., Madison, Wisconcin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Guru Row, T. N. (1999). Chem. Rev. 183, 81—100. Google Scholar
Jotani, M. M., Baldaniya, B. B. & Jasinski, J. P. (2009). J. Chem. Crystallogr. 39, 898–901. Web of Science CSD CrossRef CAS Google Scholar
Krishnamurthy, M. S., Nagarajaiah, H. & Begum, N. S. (2014). Acta Cryst. E70, o1187–o1188. CSD CrossRef IUCr Journals Google Scholar
Nagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444. 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
Yamazaki, T., Taguchi, T. & Ojima, I. (2009). Fluorine in Medicinal Chemistry and Chemical Biology, edited by I. Ojima, pp. 3–46. Weinheim: Wiley-Blackwell. 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 70| Part 12| December 2014| Pages o1270-o1271

doi:10.1107/S1600536814025008

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

Crystal structure of ethyl 2-(2-fluoro­benzyl­­idene)-5-(4-fluoro­phen­yl)-7-methyl-3-oxo-2,3-di­hydro-5H-1,3-thia­zolo[3,2-a]pyrimidine-6-carb­­oxy­late

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of ethyl 2-(2-fluorobenzylidene)-5-(4-fluorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate