4-Fluoro-N-[3-(2-fluoro­phen­yl)-4-methyl-2,3-dihydro-2-thienyl­idene]benzamide

Saeed, A.; Shaheen, U.; Latif, M.; Bolte, M.

doi:10.1107/S1600536809022314

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1643

doi:10.1107/S1600536809022314

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4-Fluoro-N-[3-(2-fluorophenyl)-4-methyl-2,3-dihydro-2-thienylidene]benzamide

Aamer Saeed,^a ^* Uzma Shaheen,^a Muhammad Latif ^b and Michael Bolte ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bHamdard Institute of Pharmaceutical Sciences, Hamdard University, Islamabad Campus, Pakistan, and ^cInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 13 May 2009; accepted 11 June 2009; online 20 June 2009)

In the title compound, C₁₇H₁₂F₂N₂OS, the planar thiazole ring (r.m.s. deviation = 0.012 Å) makes dihedral angles of 15.08 (9) and 81.81 (6)° with the 4-fluorophenyl and 2-fluorophenyl rings, respectively. The 2-fluorophenyl ring is disordered over two orientations with site-occupancy factors of 0.810 (3) and 0.190 (3). The structure contains intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of imino-1,3-thiazoline derivatives, see: Kim et al. (2007 ); Vicini et al. (2006 ); Hosseinimehr et al. (2001 ); Zhang et al. (2000 ); Pietrancosta et al. (2006 ). For details of the synthesis, see: Saeed et al. (2008a ). For a related structure, see: Saeed et al. (2008b ).

Experimental

Crystal data

C₁₇H₁₂F₂N₂OS
M_r = 330.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.0982 (14) Å
b = 11.423 (2) Å
c = 18.949 (4) Å
V = 1536.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.36 × 0.34 × 0.28 mm

Data collection

Stoe IPDS-II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ; Blessing, 1995 ) T_min = 0.920, T_max = 0.937
10484 measured reflections
3531 independent reflections
3213 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.082
S = 0.99
3531 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 1491 Friedel pairs
Flack parameter: −0.15 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.95	2.41	3.322 (2)	160
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022314/bi2375sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022314/bi2375Isup2.hkl

checkCIF report

Comment top

The imino-1,3-thiazoline group is found in a variety of biologically active natural products and finds extensive applications in medicinal chemistry. 2-Thiazolylimino-5-arylidene-4-thiazolidinones show noticeable antimicrobial activity against bacteria, yeasts and mould (Kim et al., 2007). 3-Substituted 2-(cyanoimino)thiazolidines can be used in agriculture due to their neonicotinoid insecticidal activity (Vicini et al., 2006). 3-Substituted thiazolidines show radioprotective properties against γ-radiation (Hosseinimehr et al., 2001). KHG22394, a 2-imino-1,3-thiazoline derivative, significantly inhibits melanin production in a dose-dependent manner, thus acting as a skin whitening agent (Zhang et al., 2000) and pifithrin-alpha, another iminothiazoline, is a reversible inhibitor of p53-mediated apoptosis and p53-dependent gene transcription (Pietrancosta et al., 2006).

Related literature top

For the biological activity of imino-1,3-thiazoline derivatives, see: Kim et al. (2007); Vicini et al. (2006); Hosseinimehr et al. (2001); Zhang et al. (2000); Pietrancosta et al. (2006). For details of the synthesis, see: Saeed et al. (2008a). For a related structure, see: Saeed et al. (2008b).

Experimental top

The title compound was prepared according to the procedure reported earlier (Saeed et al. (2008a). Crystallization of the residue in CHCl₃ afforded the title compound (81%) as white needles: Anal. calcd. for C₁₄H₁₂Cl_NO1: C 68.44, H 4.92, N 5.70%; found: C 68.39, H 4.90, N 5.67%

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering scheme; displacement ellipsoids are at the 50% probability level; H atoms are drawn as small spheres of arbitrary radii. The atoms of the minor occupied sites have been omitted for clarity.

4-Fluoro-N-[3-(2-fluorophenyl)-4-methyl-2,3-dihydro-2- thienylidene]benzamide top

Crystal data top

C₁₇H₁₂F₂N₂OS	F(000) = 680
M_r = 330.35	D_x = 1.428 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9675 reflections
a = 7.0982 (14) Å	θ = 3.4–27.8°
b = 11.423 (2) Å	µ = 0.24 mm⁻¹
c = 18.949 (4) Å	T = 173 K
V = 1536.5 (5) Å³	Block, colourless
Z = 4	0.36 × 0.34 × 0.28 mm

Data collection top

Stoe IPDS-II two-circle diffractometer	3531 independent reflections
Radiation source: fine-focus sealed tube	3213 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 27.6°, θ_min = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −8→9
T_min = 0.920, T_max = 0.937	k = −12→14
10484 measured reflections	l = −24→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.052P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
3531 reflections	Δρ_max = 0.15 e Å⁻³
219 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1491 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.15 (6)

Crystal data top

C₁₇H₁₂F₂N₂OS	V = 1536.5 (5) Å³
M_r = 330.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.0982 (14) Å	µ = 0.24 mm⁻¹
b = 11.423 (2) Å	T = 173 K
c = 18.949 (4) Å	0.36 × 0.34 × 0.28 mm

Data collection top

Stoe IPDS-II two-circle diffractometer	3531 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	3213 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.937	R_int = 0.046
10484 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.082	Δρ_max = 0.15 e Å⁻³
S = 0.99	Δρ_min = −0.26 e Å⁻³
3531 reflections	Absolute structure: Flack (1983), 1491 Friedel pairs
219 parameters	Absolute structure parameter: −0.15 (6)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.86255 (5)	0.65177 (5)	0.73205 (2)	0.04103 (12)
N1	0.56925 (19)	0.59033 (13)	0.64274 (7)	0.0316 (3)
O1	0.7594 (2)	0.44060 (14)	0.68401 (8)	0.0520 (4)
F1	0.0840 (3)	0.15356 (14)	0.55262 (9)	0.0825 (5)
F2	0.71228 (15)	0.86728 (14)	0.53579 (6)	0.0406 (4)	0.810 (3)
F2'	0.2818 (7)	0.7551 (6)	0.7021 (3)	0.048 (2)	0.190 (3)
C1	0.6168 (2)	0.47540 (16)	0.65201 (8)	0.0356 (4)
C2	0.67222 (19)	0.66920 (16)	0.67514 (8)	0.0303 (3)
N3	0.63342 (18)	0.78545 (13)	0.66789 (7)	0.0304 (3)
C4	0.7456 (2)	0.86166 (18)	0.70871 (8)	0.0340 (4)
C5	0.8742 (2)	0.80204 (19)	0.74587 (9)	0.0414 (4)
H5	0.9626	0.8381	0.7766	0.050*
C6	0.7117 (3)	0.98996 (19)	0.70565 (10)	0.0436 (4)
H6A	0.7834	1.0287	0.7432	0.065*
H6B	0.5771	1.0056	0.7121	0.065*
H6C	0.7523	1.0201	0.6597	0.065*
C11	0.4788 (3)	0.39042 (17)	0.62212 (8)	0.0353 (4)
C12	0.5145 (3)	0.27036 (19)	0.62624 (10)	0.0451 (4)
H12	0.6301	0.2435	0.6457	0.054*
C13	0.3827 (3)	0.19005 (18)	0.60216 (10)	0.0513 (5)
H13	0.4062	0.1083	0.6052	0.062*
C14	0.2173 (3)	0.2315 (2)	0.57387 (11)	0.0529 (5)
C15	0.1774 (3)	0.3489 (2)	0.56784 (11)	0.0519 (5)
H15	0.0622	0.3747	0.5476	0.062*
C16	0.3098 (3)	0.42878 (17)	0.59203 (10)	0.0405 (4)
H16	0.2854	0.5103	0.5881	0.049*
C21	0.48714 (19)	0.82453 (15)	0.62105 (8)	0.0278 (3)
C22	0.5303 (2)	0.86227 (15)	0.55392 (8)	0.0290 (3)
H22	0.6587	0.8661	0.5400	0.035*	0.190 (3)
C23	0.3925 (2)	0.89464 (15)	0.50637 (8)	0.0325 (3)
H23	0.4250	0.9201	0.4602	0.039*
C24	0.2054 (2)	0.88918 (16)	0.52746 (9)	0.0348 (4)
H24	0.1085	0.9107	0.4954	0.042*
C25	0.1592 (2)	0.8527 (2)	0.59472 (9)	0.0439 (4)
H25	0.0309	0.8499	0.6089	0.053*
C26	0.2997 (2)	0.8203 (2)	0.64164 (9)	0.0403 (4)
H26	0.2675	0.7945	0.6877	0.048*	0.810 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02961 (17)	0.0565 (3)	0.0369 (2)	0.00724 (19)	−0.00870 (15)	0.0061 (2)
N1	0.0334 (6)	0.0324 (8)	0.0290 (6)	0.0029 (5)	−0.0029 (5)	0.0041 (6)
O1	0.0474 (7)	0.0475 (9)	0.0610 (8)	0.0136 (6)	−0.0158 (6)	0.0073 (7)
F1	0.1076 (11)	0.0365 (7)	0.1034 (11)	−0.0068 (8)	−0.0504 (9)	−0.0073 (8)
F2	0.0270 (6)	0.0573 (10)	0.0374 (6)	−0.0039 (5)	0.0046 (4)	0.0079 (6)
F2'	0.032 (3)	0.074 (5)	0.038 (3)	0.005 (3)	0.006 (2)	0.014 (3)
C1	0.0391 (8)	0.0375 (9)	0.0302 (7)	0.0106 (8)	−0.0003 (6)	0.0046 (7)
C2	0.0263 (6)	0.0403 (10)	0.0242 (6)	0.0023 (6)	−0.0005 (5)	0.0036 (6)
N3	0.0260 (5)	0.0362 (7)	0.0290 (6)	−0.0027 (6)	−0.0054 (5)	0.0023 (5)
C4	0.0269 (6)	0.0454 (11)	0.0299 (7)	−0.0076 (7)	−0.0004 (5)	−0.0033 (7)
C5	0.0288 (7)	0.0603 (12)	0.0351 (8)	−0.0059 (7)	−0.0074 (6)	−0.0013 (7)
C6	0.0402 (8)	0.0462 (12)	0.0443 (9)	−0.0112 (8)	−0.0037 (7)	−0.0079 (8)
C11	0.0460 (9)	0.0325 (9)	0.0275 (7)	0.0087 (7)	−0.0001 (6)	0.0021 (6)
C12	0.0590 (11)	0.0372 (10)	0.0391 (9)	0.0129 (9)	−0.0036 (8)	−0.0004 (8)
C13	0.0751 (13)	0.0302 (10)	0.0485 (10)	0.0111 (9)	−0.0098 (10)	−0.0064 (8)
C14	0.0751 (13)	0.0332 (11)	0.0504 (11)	−0.0010 (10)	−0.0168 (10)	−0.0057 (9)
C15	0.0656 (11)	0.0348 (10)	0.0553 (11)	0.0055 (9)	−0.0237 (9)	−0.0007 (10)
C16	0.0525 (10)	0.0295 (9)	0.0395 (8)	0.0064 (7)	−0.0111 (7)	0.0015 (8)
C21	0.0262 (6)	0.0285 (8)	0.0288 (7)	−0.0004 (6)	−0.0037 (5)	0.0016 (6)
C22	0.0280 (6)	0.0278 (8)	0.0314 (7)	−0.0019 (6)	0.0010 (5)	0.0002 (6)
C23	0.0409 (8)	0.0299 (8)	0.0267 (7)	−0.0024 (7)	−0.0022 (6)	0.0021 (6)
C24	0.0335 (7)	0.0363 (9)	0.0346 (8)	0.0029 (7)	−0.0097 (6)	−0.0014 (7)
C25	0.0258 (6)	0.0679 (13)	0.0379 (8)	0.0020 (8)	−0.0020 (6)	0.0010 (9)
C26	0.0290 (7)	0.0615 (13)	0.0305 (7)	−0.0027 (8)	−0.0009 (6)	0.0070 (8)

Geometric parameters (Å, º) top

S1—C5	1.738 (2)	C12—C13	1.388 (3)
S1—C2	1.7400 (15)	C12—H12	0.950
N1—C2	1.313 (2)	C13—C14	1.375 (3)
N1—C1	1.367 (2)	C13—H13	0.950
O1—C1	1.245 (2)	C14—C15	1.376 (3)
F1—C14	1.360 (3)	C15—C16	1.387 (3)
F2—C22	1.3379 (18)	C15—H15	0.950
F2'—C26	1.373 (6)	C16—H16	0.950
C1—C11	1.491 (3)	C21—C22	1.378 (2)
C2—N3	1.363 (2)	C21—C26	1.387 (2)
N3—C4	1.411 (2)	C22—C23	1.380 (2)
N3—C21	1.4370 (18)	C22—H22	0.950
C4—C5	1.339 (2)	C23—C24	1.388 (2)
C4—C6	1.486 (3)	C23—H23	0.950
C5—H5	0.950	C24—C25	1.380 (2)
C6—H6A	0.980	C24—H24	0.950
C6—H6B	0.980	C25—C26	1.386 (2)
C6—H6C	0.980	C25—H25	0.950
C11—C12	1.397 (3)	C26—H26	0.950
C11—C16	1.399 (2)

C5—S1—C2	90.99 (8)	F1—C14—C13	119.0 (2)
C2—N1—C1	117.49 (14)	F1—C14—C15	118.1 (2)
O1—C1—N1	124.75 (18)	C13—C14—C15	122.9 (2)
O1—C1—C11	120.75 (17)	C14—C15—C16	118.31 (19)
N1—C1—C11	114.48 (14)	C14—C15—H15	120.8
N1—C2—N3	120.60 (13)	C16—C15—H15	120.8
N1—C2—S1	130.07 (14)	C15—C16—C11	120.64 (18)
N3—C2—S1	109.32 (12)	C15—C16—H16	119.7
C2—N3—C4	115.58 (14)	C11—C16—H16	119.7
C2—N3—C21	120.72 (13)	C22—C21—C26	118.93 (14)
C4—N3—C21	123.70 (15)	C22—C21—N3	120.45 (13)
C5—C4—N3	111.06 (17)	C26—C21—N3	120.56 (14)
C5—C4—C6	129.23 (16)	F2—C22—C21	117.72 (14)
N3—C4—C6	119.71 (15)	F2—C22—C23	120.34 (14)
C4—C5—S1	113.00 (13)	C21—C22—C23	121.94 (14)
C4—C5—H5	123.5	C21—C22—H22	118.9
S1—C5—H5	123.5	C23—C22—H22	119.1
C4—C6—H6A	109.5	C22—C23—C24	118.55 (15)
C4—C6—H6B	109.5	C22—C23—H23	120.7
H6A—C6—H6B	109.5	C24—C23—H23	120.7
C4—C6—H6C	109.5	C25—C24—C23	120.43 (14)
H6A—C6—H6C	109.5	C25—C24—H24	119.8
H6B—C6—H6C	109.5	C23—C24—H24	119.8
C12—C11—C16	119.08 (18)	C24—C25—C26	120.12 (14)
C12—C11—C1	119.91 (16)	C24—C25—H25	119.9
C16—C11—C1	120.96 (16)	C26—C25—H25	119.9
C13—C12—C11	120.54 (18)	F2'—C26—C25	127.8 (3)
C13—C12—H12	119.7	F2'—C26—C21	110.0 (3)
C11—C12—H12	119.7	C25—C26—C21	120.02 (15)
C14—C13—C12	118.5 (2)	C25—C26—H26	119.9
C14—C13—H13	120.8	C21—C26—H26	120.0
C12—C13—H13	120.8

C2—N1—C1—O1	−6.3 (3)	C12—C13—C14—C15	0.6 (3)
C2—N1—C1—C11	171.87 (14)	F1—C14—C15—C16	177.5 (2)
C1—N1—C2—N3	179.61 (14)	C13—C14—C15—C16	−0.6 (4)
C1—N1—C2—S1	−2.0 (2)	C14—C15—C16—C11	−0.4 (3)
C5—S1—C2—N1	−176.30 (15)	C12—C11—C16—C15	1.3 (3)
C5—S1—C2—N3	2.19 (11)	C1—C11—C16—C15	−176.43 (18)
N1—C2—N3—C4	176.05 (13)	C2—N3—C21—C22	−97.29 (18)
S1—C2—N3—C4	−2.61 (15)	C4—N3—C21—C22	82.51 (19)
N1—C2—N3—C21	−4.1 (2)	C2—N3—C21—C26	80.0 (2)
S1—C2—N3—C21	177.21 (10)	C4—N3—C21—C26	−100.2 (2)
C2—N3—C4—C5	1.65 (19)	C26—C21—C22—F2	178.95 (18)
C21—N3—C4—C5	−178.16 (13)	N3—C21—C22—F2	−3.7 (2)
C2—N3—C4—C6	−178.75 (14)	C26—C21—C22—C23	−0.8 (3)
C21—N3—C4—C6	1.4 (2)	N3—C21—C22—C23	176.59 (16)
N3—C4—C5—S1	0.14 (17)	F2—C22—C23—C24	−179.43 (18)
C6—C4—C5—S1	−179.40 (14)	C21—C22—C23—C24	0.3 (3)
C2—S1—C5—C4	−1.36 (13)	C22—C23—C24—C25	0.4 (3)
O1—C1—C11—C12	−3.8 (3)	C23—C24—C25—C26	−0.5 (3)
N1—C1—C11—C12	177.96 (16)	C24—C25—C26—F2'	−161.8 (4)
O1—C1—C11—C16	173.91 (17)	C24—C25—C26—C21	0.0 (3)
N1—C1—C11—C16	−4.3 (2)	C22—C21—C26—F2'	165.4 (3)
C16—C11—C12—C13	−1.3 (3)	N3—C21—C26—F2'	−12.0 (4)
C1—C11—C12—C13	176.43 (16)	C22—C21—C26—C25	0.6 (3)
C11—C12—C13—C14	0.4 (3)	N3—C21—C26—C25	−176.76 (18)
C12—C13—C14—F1	−177.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.41	3.322 (2)	160

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂F₂N₂OS
M_r	330.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	7.0982 (14), 11.423 (2), 18.949 (4)
V (Å³)	1536.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.36 × 0.34 × 0.28

Data collection
Diffractometer	Stoe IPDS-II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.920, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	10484, 3531, 3213
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.082, 0.99
No. of reflections	3531
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.26
Absolute structure	Flack (1983), 1491 Friedel pairs
Absolute structure parameter	−0.15 (6)

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.41	3.322 (2)	160.1

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

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hosseinimehr, S. J. A., Shafiee, A. H., Mozdarani, H. S. & Akhlagpour, S. (2001). J. Radiat. Res. (Tokyo), 42, 401–408. Web of Science CrossRef PubMed CAS Google Scholar
Kim, D.-S., Jeong, Y.-M., Park, I.-K., Hahn, H.-G. & Lee, H.-K. (2007). Biol. Pharm. Bull. 30, 180–184. Web of Science CrossRef PubMed CAS Google Scholar
Pietrancosta, N., Moumen, A., Dono, R., Lingor, P., Planchamp, V., Lamballe, F., Bähr, M., Kraus, J.-L. & Maina, F. (2006). J. Med. Chem. 49, 3645–3652. Web of Science CrossRef PubMed CAS Google Scholar
Saeed, A., Zaman, S. & Bolte, M. (2008a). Synth. Commun. 38, 2185–2199. Web of Science CSD CrossRef CAS Google Scholar
Saeed, A., Zaman, S. & Bolte, M. (2008b). Acta Cryst. E64, o67. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Vicini, P., Geronikaki, A., Anastasia, K., Incerti, M. & Zani, F. (2006). Bioorg. Med. Chem. 14, 3859–3864. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, A. G., Kayser, H., Maienfisch, P. & Casida, J. E. (2000). J. Neurochem. 75, 1294–1303. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 65| Part 7| July 2009| Page o1643

doi:10.1107/S1600536809022314

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

4-Fluoro-N-[3-(2-fluoro­phen­yl)-4-methyl-2,3-di­hydro-2-thienyl­­idene]benzamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

4-Fluoro-N-[3-(2-fluorophenyl)-4-methyl-2,3-dihydro-2-thienylidene]benzamide