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

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

doi:10.1107/S1600536814023010

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1187-o1188

doi:10.1107/S1600536814023010

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

M. S. Krishnamurthy,^a H. Nagarajaiah ^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 May 2014; accepted 20 October 2014; online 24 October 2014)

In the title molecule, C₂₃H₁₈F₂N₂O₃S, the pyrimidine ring is in a half-chair conformation and the 3-fluorophenyl group is in the axial position. The thiazole ring (r.m.s. deviation = 0.0252 Å) forms dihedral angles of 84.8 (7) and 9.6 (7)° with the 3-fluoro-substituted and 4-fluoro-substituted benzene rings, respectively. In the crystal, weak C—H⋯F and C—H⋯O hydrogen bonds connect molecules, forming zigzag chains along the b axis. In addition π–π stacking interactions with a centroid–centroid distance of 3.7633 (9) Å connect these chains into ladders via inversion-related 4-fluorophenyl groups.

Keywords: crystal structure; pyrimidine; thiazole; hydrogen bonds; π–π stacking interactions.

CCDC reference: 1029845

1. Related literature

For the pharmacological properties of pyrimidine derivatives, see: Alam et al. (2010 ); Kulakov et al. (2009 ); Ashok et al. (2007 ). For examples of compounds with weak intermolecular interactions, see: Prasanna & Guru Row (2001 ); Yamazaki et al. (2009 ). For related structures, see: Fischer et al. (2007 ); Zhao et al. (2011 ); Nagarajaiah & Begum (2011 ).

2. Experimental

2.1. Crystal data

C₂₃H₁₈F₂N₂O₃S
M_r = 440.45
Monoclinic, P 2₁ /n
a = 9.4358 (5) Å
b = 10.7862 (6) Å
c = 20.2246 (11) Å
β = 92.159 (1)°
V = 2056.93 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.18 × 0.16 × 0.16 mm

2.2. Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.964, T_max = 0.968
15631 measured reflections
4480 independent reflections
3890 reflections with I > 2σ(I)
R_int = 0.026

2.3. Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 1.06
4480 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯F1ⁱ	0.95	2.53	3.437 (2)	159
C13—H13⋯F1ⁱⁱ	0.95	2.56	3.513 (2)	178
C14—H14⋯O1ⁱⁱ	0.95	2.36	3.303 (2)	172
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

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

CCDC reference: 1029845

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814023010/lh5711sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023010/lh5711Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814023010/lh5711Isup3.cml

checkCIF report

Comment top

Pyrimidine derivatives are of interest because of their useful biological and therapeutic activities (Ashok et al., 2007). The presence of both pyrimidine and thiazole rings results in enhanced activity (Alam et al., 2010; Kulakov et al., 2009). Intermolecular interactions of the type C—H···F and C—F···π can supply both directional and actively favorable pathways to hold the molecules together in the crystalline lattice that offer additional stability (Prasanna & Guru Row, 2001; Yamazaki et al., 2009). Herein, we report the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The 3-fluoro phenyl ring adopts a syn periplanar conformation with respect to C5—H5 bond of the pyrimidine ring. The pyrimidine ring is in a half-chair conformation with atoms N1 and C5 displaced by -0.110 (1) and 0.168 (1) Å from the mean plane of the other four atoms (N2/C6/C7/C9 with a maximun deviation of 0.042 (1)Å for both atoms N2 and C7). The 3-fluorophenyl group is in the axial position. The thiazole ring (r.m.s. deviation = 0.0252 Å) forms dihedral angles of 84.8 (7) and 9.6 (7)° with the 3-fluoro-substituted and 4-fluoro-substituted benzene rings respectively. The exocyclic ester group at C6 adopts cis orientation with respect to C6═C7 double bond. The bond and angles in the title compound agree with the corresponding bond distances and angles reported in related compounds (Fischer et al., 2007; Zhao et al., 2011; Nagarajaiah & Begum, 2011). In the crystal, weak C—H···F and C—H···O hydrogen bonds connect molecules forming zigzag chains along the b axis (Fig. 2). In addition π–π stacking interactions with a centroid–centroid distance of 3.7633 (9)Å connect these chains into ladders via inversion-related 4-fluorophenyl groups.

Related literature top

For the pharmacological properties of pyrimidine derivatives, see: Alam et al. (2010); Kulakov et al. (2009); Ashok et al. (2007). For examples of compounds with weak intermolecular interactions, see: Prasanna & Guru Row (2001); Yamazaki et al. (2009). For related structures, see: Fischer et al. (2007); Zhao et al. (2011); Nagarajaiah & Begum (2011).

Experimental top

A mixture of 4-(3-fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro- pyrimidine-5-carboxylic acid ethyl ester (10 mmol), chloroacetic acid (10 mmol), 4-fluorobenzaldehyde (10 mmol) and sodium acetate (1.5 g) was taken 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 (76% yield, mp 460 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-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

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

Figure 2. Part of the crystal structure showing intermolecular interactions with dotted lines. H-atoms not involved in hydrogen bonds have been excluded.

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

Crystal data top

C₂₃H₁₈F₂N₂O₃S	F(000) = 912
M_r = 440.45	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4480 reflections
a = 9.4358 (5) Å	θ = 2.1–27.0°
b = 10.7862 (6) Å	µ = 0.20 mm⁻¹
c = 20.2246 (11) Å	T = 100 K
β = 92.159 (1)°	Block, yellow
V = 2056.93 (19) Å³	0.18 × 0.16 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4480 independent reflections
Radiation source: fine-focus sealed tube	3890 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→12
T_min = 0.964, T_max = 0.968	k = −13→11
15631 measured reflections	l = −25→25

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0546P)² + 0.9996P] where P = (F_o² + 2F_c²)/3
4480 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₁₈F₂N₂O₃S	V = 2056.93 (19) Å³
M_r = 440.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4358 (5) Å	µ = 0.20 mm⁻¹
b = 10.7862 (6) Å	T = 100 K
c = 20.2246 (11) Å	0.18 × 0.16 × 0.16 mm
β = 92.159 (1)°

Data collection top

Bruker SMART APEX diffractometer	4480 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3890 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.968	R_int = 0.026
15631 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	Δρ_max = 0.44 e Å⁻³
4480 reflections	Δρ_min = −0.23 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	0.88687 (4)	0.19204 (3)	0.034764 (17)	0.01589 (11)
F2	0.38224 (11)	−0.20262 (10)	0.14390 (5)	0.0344 (3)
N1	1.02387 (12)	0.21900 (11)	−0.07291 (6)	0.0130 (2)
O1	0.95802 (11)	0.05123 (9)	−0.13566 (5)	0.0168 (2)
O3	1.32012 (11)	0.35754 (11)	−0.18945 (5)	0.0234 (3)
N2	1.08494 (13)	0.36112 (12)	0.01251 (6)	0.0178 (3)
F1	0.83639 (12)	0.28603 (11)	−0.33642 (5)	0.0364 (3)
C6	1.20222 (15)	0.37625 (13)	−0.09169 (7)	0.0168 (3)
C2	0.86191 (15)	0.08022 (13)	−0.02757 (7)	0.0136 (3)
C17	0.77697 (14)	−0.01947 (13)	−0.02952 (7)	0.0145 (3)
H17	0.7813	−0.0677	−0.0687	0.017*
C9	1.01253 (15)	0.27081 (13)	−0.01116 (7)	0.0138 (3)
C11	0.99691 (15)	0.34259 (14)	−0.17420 (7)	0.0160 (3)
C5	1.10183 (15)	0.28309 (13)	−0.12475 (7)	0.0144 (3)
H5	1.1592	0.2205	−0.1485	0.017*
C18	0.67908 (15)	−0.06573 (13)	0.01880 (7)	0.0157 (3)
C21	0.48097 (17)	−0.15811 (16)	0.10318 (8)	0.0240 (3)
C7	1.19145 (15)	0.40940 (13)	−0.02781 (8)	0.0175 (3)
C16	0.96568 (17)	0.28569 (15)	−0.23478 (8)	0.0202 (3)
H16	1.0110	0.2107	−0.2466	0.024*
C3	0.94988 (14)	0.11093 (13)	−0.08497 (7)	0.0135 (3)
C20	0.48715 (17)	−0.20784 (15)	0.04067 (9)	0.0236 (3)
H20	0.4247	−0.2726	0.0267	0.028*
C19	0.58648 (16)	−0.16121 (14)	−0.00123 (8)	0.0195 (3)
H19	0.5921	−0.1946	−0.0445	0.023*
C23	0.67034 (16)	−0.01971 (15)	0.08349 (8)	0.0202 (3)
H23	0.7331	0.0442	0.0983	0.024*
C15	0.86709 (17)	0.34154 (16)	−0.27702 (7)	0.0243 (4)
C10	1.31041 (16)	0.42857 (15)	−0.13541 (8)	0.0235 (3)
O2	1.37971 (16)	0.52124 (13)	−0.12605 (8)	0.0448 (4)
C13	0.83007 (17)	0.50531 (16)	−0.20222 (9)	0.0266 (4)
H13	0.7836	0.5800	−0.1908	0.032*
C12	0.92960 (16)	0.45299 (15)	−0.15833 (8)	0.0206 (3)
H12	0.9519	0.4926	−0.1173	0.025*
C1	1.28965 (17)	0.49369 (16)	0.01043 (9)	0.0253 (4)
H1A	1.3665	0.5199	−0.0177	0.038*
H1B	1.3296	0.4498	0.0493	0.038*
H1C	1.2373	0.5667	0.0248	0.038*
C22	0.57151 (17)	−0.06610 (15)	0.12598 (8)	0.0235 (3)
H22	0.5663	−0.0352	0.1698	0.028*
C14	0.79808 (17)	0.44933 (16)	−0.26257 (8)	0.0265 (4)
H14	0.7303	0.4846	−0.2930	0.032*
C8	1.41942 (18)	0.39730 (18)	−0.23844 (9)	0.0309 (4)
H8A	1.5130	0.4160	−0.2170	0.037*
H8B	1.3840	0.4728	−0.2615	0.037*
C4	1.4318 (2)	0.29285 (19)	−0.28635 (9)	0.0358 (4)
H4A	1.4729	0.2205	−0.2635	0.054*
H4B	1.4931	0.3178	−0.3221	0.054*
H4C	1.3375	0.2717	−0.3050	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01805 (19)	0.01604 (19)	0.01374 (18)	−0.00094 (13)	0.00276 (13)	−0.00157 (13)
F2	0.0247 (5)	0.0389 (6)	0.0406 (6)	−0.0027 (4)	0.0143 (4)	0.0164 (5)
N1	0.0131 (6)	0.0139 (6)	0.0121 (5)	−0.0001 (4)	0.0003 (4)	0.0014 (4)
O1	0.0185 (5)	0.0175 (5)	0.0147 (5)	−0.0020 (4)	0.0024 (4)	−0.0026 (4)
O3	0.0197 (6)	0.0269 (6)	0.0238 (6)	−0.0057 (5)	0.0057 (4)	0.0064 (5)
N2	0.0167 (6)	0.0160 (6)	0.0206 (6)	−0.0004 (5)	−0.0012 (5)	−0.0029 (5)
F1	0.0456 (7)	0.0419 (6)	0.0206 (5)	−0.0067 (5)	−0.0127 (5)	0.0051 (4)
C6	0.0127 (7)	0.0136 (7)	0.0238 (7)	−0.0002 (5)	−0.0023 (6)	0.0026 (6)
C2	0.0131 (6)	0.0147 (7)	0.0131 (6)	0.0026 (5)	−0.0002 (5)	0.0006 (5)
C17	0.0130 (7)	0.0154 (7)	0.0152 (7)	0.0028 (5)	0.0000 (5)	0.0014 (5)
C9	0.0133 (6)	0.0139 (6)	0.0143 (6)	0.0030 (5)	−0.0002 (5)	0.0009 (5)
C11	0.0126 (7)	0.0176 (7)	0.0178 (7)	−0.0033 (5)	0.0008 (5)	0.0060 (6)
C5	0.0120 (6)	0.0147 (7)	0.0167 (7)	−0.0012 (5)	0.0022 (5)	0.0025 (5)
C18	0.0132 (7)	0.0133 (7)	0.0207 (7)	0.0033 (5)	0.0014 (5)	0.0053 (6)
C21	0.0165 (7)	0.0255 (8)	0.0306 (8)	0.0042 (6)	0.0085 (6)	0.0141 (7)
C7	0.0125 (7)	0.0124 (7)	0.0273 (8)	0.0010 (5)	−0.0025 (6)	−0.0005 (6)
C16	0.0215 (8)	0.0192 (7)	0.0198 (7)	−0.0027 (6)	0.0003 (6)	0.0050 (6)
C3	0.0116 (6)	0.0144 (7)	0.0142 (6)	0.0012 (5)	−0.0017 (5)	0.0020 (5)
C20	0.0157 (7)	0.0179 (8)	0.0373 (9)	−0.0015 (6)	0.0006 (6)	0.0084 (7)
C19	0.0164 (7)	0.0169 (7)	0.0252 (8)	0.0022 (6)	0.0001 (6)	0.0041 (6)
C23	0.0191 (7)	0.0193 (7)	0.0222 (7)	0.0007 (6)	0.0021 (6)	0.0044 (6)
C15	0.0247 (8)	0.0309 (9)	0.0169 (7)	−0.0095 (7)	−0.0038 (6)	0.0071 (7)
C10	0.0166 (7)	0.0215 (8)	0.0323 (9)	−0.0025 (6)	0.0007 (6)	0.0042 (7)
O2	0.0439 (8)	0.0382 (8)	0.0535 (9)	−0.0277 (7)	0.0159 (7)	−0.0068 (7)
C13	0.0195 (8)	0.0275 (9)	0.0329 (9)	0.0055 (6)	0.0019 (7)	0.0090 (7)
C12	0.0186 (7)	0.0208 (8)	0.0226 (7)	0.0010 (6)	0.0010 (6)	0.0039 (6)
C1	0.0181 (8)	0.0214 (8)	0.0361 (9)	−0.0035 (6)	−0.0021 (7)	−0.0083 (7)
C22	0.0237 (8)	0.0254 (8)	0.0217 (8)	0.0044 (6)	0.0059 (6)	0.0072 (6)
C14	0.0171 (7)	0.0336 (9)	0.0285 (8)	−0.0019 (6)	−0.0037 (6)	0.0160 (7)
C8	0.0229 (8)	0.0393 (10)	0.0311 (9)	−0.0082 (7)	0.0091 (7)	0.0114 (8)
C4	0.0371 (10)	0.0491 (12)	0.0219 (8)	−0.0069 (9)	0.0088 (7)	0.0084 (8)

Geometric parameters (Å, º) top

S1—C9	1.7531 (14)	C21—C22	1.378 (2)
S1—C2	1.7542 (14)	C7—C1	1.493 (2)
F2—C21	1.3544 (17)	C16—C15	1.378 (2)
N1—C3	1.3758 (18)	C16—H16	0.9500
N1—C9	1.3761 (18)	C20—C19	1.382 (2)
N1—C5	1.4753 (17)	C20—H20	0.9500
O1—C3	1.2154 (17)	C19—H19	0.9500
O3—C10	1.341 (2)	C23—C22	1.385 (2)
O3—C8	1.4538 (18)	C23—H23	0.9500
N2—C9	1.2728 (19)	C15—C14	1.370 (3)
N2—C7	1.4171 (19)	C10—O2	1.206 (2)
F1—C15	1.3636 (19)	C13—C14	1.385 (2)
C6—C7	1.348 (2)	C13—C12	1.388 (2)
C6—C10	1.487 (2)	C13—H13	0.9500
C6—C5	1.519 (2)	C12—H12	0.9500
C2—C17	1.341 (2)	C1—H1A	0.9800
C2—C3	1.4897 (18)	C1—H1B	0.9800
C17—C18	1.4578 (19)	C1—H1C	0.9800
C17—H17	0.9500	C22—H22	0.9500
C11—C16	1.392 (2)	C14—H14	0.9500
C11—C12	1.393 (2)	C8—C4	1.493 (3)
C11—C5	1.5222 (19)	C8—H8A	0.9900
C5—H5	1.0000	C8—H8B	0.9900
C18—C19	1.401 (2)	C4—H4A	0.9800
C18—C23	1.405 (2)	C4—H4B	0.9800
C21—C20	1.376 (2)	C4—H4C	0.9800

C9—S1—C2	91.59 (7)	C19—C20—H20	120.8
C3—N1—C9	116.66 (12)	C20—C19—C18	121.37 (15)
C3—N1—C5	122.30 (11)	C20—C19—H19	119.3
C9—N1—C5	120.84 (12)	C18—C19—H19	119.3
C10—O3—C8	116.91 (13)	C22—C23—C18	120.98 (15)
C9—N2—C7	116.55 (12)	C22—C23—H23	119.5
C7—C6—C10	123.20 (14)	C18—C23—H23	119.5
C7—C6—C5	121.96 (13)	F1—C15—C14	118.29 (15)
C10—C6—C5	114.84 (13)	F1—C15—C16	118.06 (16)
C17—C2—C3	120.36 (13)	C14—C15—C16	123.65 (15)
C17—C2—S1	129.53 (11)	O2—C10—O3	123.27 (15)
C3—C2—S1	110.09 (10)	O2—C10—C6	127.00 (16)
C2—C17—C18	130.38 (13)	O3—C10—C6	109.72 (13)
C2—C17—H17	114.8	C14—C13—C12	120.42 (16)
C18—C17—H17	114.8	C14—C13—H13	119.8
N2—C9—N1	126.38 (13)	C12—C13—H13	119.8
N2—C9—S1	122.40 (11)	C13—C12—C11	120.25 (15)
N1—C9—S1	111.18 (10)	C13—C12—H12	119.9
C16—C11—C12	119.77 (14)	C11—C12—H12	119.9
C16—C11—C5	120.22 (13)	C7—C1—H1A	109.5
C12—C11—C5	120.00 (13)	C7—C1—H1B	109.5
N1—C5—C6	108.45 (11)	H1A—C1—H1B	109.5
N1—C5—C11	109.58 (11)	C7—C1—H1C	109.5
C6—C5—C11	112.94 (12)	H1A—C1—H1C	109.5
N1—C5—H5	108.6	H1B—C1—H1C	109.5
C6—C5—H5	108.6	C21—C22—C23	118.42 (15)
C11—C5—H5	108.6	C21—C22—H22	120.8
C19—C18—C23	118.12 (13)	C23—C22—H22	120.8
C19—C18—C17	117.51 (13)	C15—C14—C13	117.95 (15)
C23—C18—C17	124.36 (14)	C15—C14—H14	121.0
F2—C21—C20	118.31 (15)	C13—C14—H14	121.0
F2—C21—C22	118.93 (15)	O3—C8—C4	106.72 (14)
C20—C21—C22	122.76 (14)	O3—C8—H8A	110.4
C6—C7—N2	122.33 (13)	C4—C8—H8A	110.4
C6—C7—C1	126.18 (14)	O3—C8—H8B	110.4
N2—C7—C1	111.43 (13)	C4—C8—H8B	110.4
C15—C16—C11	117.95 (15)	H8A—C8—H8B	108.6
C15—C16—H16	121.0	C8—C4—H4A	109.5
C11—C16—H16	121.0	C8—C4—H4B	109.5
O1—C3—N1	123.41 (12)	H4A—C4—H4B	109.5
O1—C3—C2	126.46 (13)	C8—C4—H4C	109.5
N1—C3—C2	110.13 (12)	H4A—C4—H4C	109.5
C21—C20—C19	118.32 (15)	H4B—C4—H4C	109.5
C21—C20—H20	120.8

C9—S1—C2—C17	179.32 (14)	C9—N1—C3—O1	−174.93 (13)
C9—S1—C2—C3	−2.35 (10)	C5—N1—C3—O1	10.2 (2)
C3—C2—C17—C18	−177.86 (13)	C9—N1—C3—C2	4.85 (17)
S1—C2—C17—C18	0.3 (2)	C5—N1—C3—C2	−169.99 (12)
C7—N2—C9—N1	−2.8 (2)	C17—C2—C3—O1	−2.5 (2)
C7—N2—C9—S1	174.64 (10)	S1—C2—C3—O1	178.97 (12)
C3—N1—C9—N2	170.94 (14)	C17—C2—C3—N1	177.70 (13)
C5—N1—C9—N2	−14.1 (2)	S1—C2—C3—N1	−0.80 (14)
C3—N1—C9—S1	−6.71 (15)	F2—C21—C20—C19	179.07 (13)
C5—N1—C9—S1	168.21 (10)	C22—C21—C20—C19	−1.5 (2)
C2—S1—C9—N2	−172.76 (13)	C21—C20—C19—C18	0.0 (2)
C2—S1—C9—N1	5.00 (11)	C23—C18—C19—C20	1.2 (2)
C3—N1—C5—C6	−164.71 (12)	C17—C18—C19—C20	−177.90 (14)
C9—N1—C5—C6	20.67 (17)	C19—C18—C23—C22	−1.0 (2)
C3—N1—C5—C11	71.60 (16)	C17—C18—C23—C22	178.08 (14)
C9—N1—C5—C11	−103.03 (14)	C11—C16—C15—F1	179.95 (13)
C7—C6—C5—N1	−13.70 (19)	C11—C16—C15—C14	−0.2 (2)
C10—C6—C5—N1	167.22 (12)	C8—O3—C10—O2	−0.4 (2)
C7—C6—C5—C11	107.95 (16)	C8—O3—C10—C6	178.65 (13)
C10—C6—C5—C11	−71.13 (16)	C7—C6—C10—O2	−16.7 (3)
C16—C11—C5—N1	−101.02 (15)	C5—C6—C10—O2	162.33 (17)
C12—C11—C5—N1	77.65 (16)	C7—C6—C10—O3	164.23 (14)
C16—C11—C5—C6	137.96 (14)	C5—C6—C10—O3	−16.70 (18)
C12—C11—C5—C6	−43.37 (17)	C14—C13—C12—C11	−0.9 (2)
C2—C17—C18—C19	169.68 (15)	C16—C11—C12—C13	1.0 (2)
C2—C17—C18—C23	−9.4 (2)	C5—C11—C12—C13	−177.68 (14)
C10—C6—C7—N2	178.12 (13)	F2—C21—C22—C23	−178.84 (14)
C5—C6—C7—N2	−0.9 (2)	C20—C21—C22—C23	1.7 (2)
C10—C6—C7—C1	−5.0 (2)	C18—C23—C22—C21	−0.4 (2)
C5—C6—C7—C1	175.96 (14)	F1—C15—C14—C13	−179.84 (14)
C9—N2—C7—C6	10.3 (2)	C16—C15—C14—C13	0.4 (2)
C9—N2—C7—C1	−166.99 (13)	C12—C13—C14—C15	0.2 (2)
C12—C11—C16—C15	−0.4 (2)	C10—O3—C8—C4	169.32 (15)
C5—C11—C16—C15	178.24 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···F1ⁱ	0.95	2.53	3.437 (2)	159
C13—H13···F1ⁱⁱ	0.95	2.56	3.513 (2)	178
C14—H14···O1ⁱⁱ	0.95	2.36	3.303 (2)	172

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···F1ⁱ	0.95	2.534	3.437 (2)	159
C13—H13···F1ⁱⁱ	0.95	2.563	3.513 (2)	178
C14—H14···O1ⁱⁱ	0.95	2.359	3.303 (2)	172

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

Acknowledgements

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

References

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Volume 70| Part 11| November 2014| Pages o1187-o1188

doi:10.1107/S1600536814023010

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

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