N′-[(2Z)-3-Allyl-4-oxo-1,3-thia­zolidin-2-yl­idene]-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide

Akkurt, M.; Karaca, S.; Cihan, G.; Çapan, G.; Büyükgüngör, O.

doi:10.1107/S1600536809012677

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1009-o1010

doi:10.1107/S1600536809012677

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N′-[(2Z)-3-Allyl-4-oxo-1,3-thiazolidin-2-ylidene]-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide

Mehmet Akkurt,^a ^* Selvi Karaca,^a Gökçe Cihan,^b Gültaze Çapan ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Istanbul, 34116 Beyazıt, Istanbul, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 2 April 2009; accepted 3 April 2009; online 8 April 2009)

In the title compound, C₂₁H₁₇FN₄O₂S, the planar indole fused-ring [maximum deviation 0.009 (1) Å] makes dihedral angles of 54.75 (9) and 14.90 (9)°, respectively, with the phenyl ring and the dihydrothiazolyl ring. The –CH2CH=CH₂ substituent is disordered over two positions in a 0.51 (1):0.49 (1) ratio. An intramolecular N—H⋯S hydrogen bond generates an S(5) ring motif. The two independent molecules are linked into a dimer by two N—H⋯O hydrogen bonds, forming an R₂²(10) ring motif. The crystal structure features intermolecular C—H⋯π and π–π stacking [centroid–centroid distance = 3.679 (1) Å] interactions. C—H⋯O and C—H⋯F interactions are also present.

Related literature

For the bactericidal, fungicidal, antitubercular and anticancer properties of 4-thiazolidinone derivatives, see: Bonde & Gaikwad (2004 ); Güzel et al. (2006 ); Küçükgüzel et al. (2002 ); Kline et al. (2008 ); Ottanà et al. (2005 ); Ulusoy (2002 ); Zhou et al. (2008 ); Çapan et al. (1999 ).

Experimental

Crystal data

C₂₁H₁₇FN₄O₂S
M_r = 408.46
Monoclinic, C 2/c
a = 21.9754 (6) Å
b = 14.7215 (5) Å
c = 16.2447 (4) Å
β = 132.022 (2)°
V = 3904.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.48 × 0.45 × 0.41 mm

Data collection

Stoe IPDS2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.910, T_max = 0.922
27187 measured reflections
4444 independent reflections
3438 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.111
S = 1.04
4444 reflections
302 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.96	2.789 (2)	161
N2—H2A⋯S1	0.86	2.52	2.925 (2)	110
C17—H17A⋯O2ⁱⁱ	0.97	2.48	3.336 (3)	147
C20B—H20B⋯F1ⁱⁱⁱ	0.93	2.37	3.284 (10)	168
C14—H14⋯Cg2ⁱⁱⁱ	0.93	2.66	3.371 (2)	134
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ . Cg2 is the centroid of the N1/C1/C6–C8 ring.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012677/ng2568sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012677/ng2568Isup2.hkl

checkCIF report

Comment top

Efforts to design, synthesize and screen new molecules that would mimic the actions of currently available chemotherapeutics have resulted in numerous promising candidates incorporating the 4-thiazolidinone system. Many 4-thiazolidinone derivatives have been shown to exhibit bactericidal (Bonde & Gaikwad, 2004; Kline et al., 2008), fungicidal (Çapan et al., 1999) antitubercular (Ulusoy, 2002; Küçükgüzel et al., 2002; Güzel et al., 2006) and anticancer (Zhou et al., 2008) properties. Furthermore the structure of 4-thiazolidinones obtained from asymmetric thiourea derivatives has been frequently discussed due to the formation of regio-isomers involving 2- and 3-positions of the thiazolidinone ring depending upon the relative nucleophilic strengths of the thioamide N atoms (Ottanà et al., 2005; Kline et al., 2008). The nitrogen involved in ene-thiolization (R₁N₁=CSH—N₂HR₂/R₁N₁HCSH=N₂R₂) determines the regiochemical outcome of the cyclization. In this context, the title compound (2) was prepared from a thiosemicarbazide precursor (1) which may be regarded as an asymmetric thiourea analogue in an attempt to obtain a new molecule with antimicrobial action and to establish its definite structure. Thus spectroscopic and X-ray diffraction studies were carried out on (2) to determine the position of the 5-fluoro-3-phenyl-2-indolylcarbonylamino residue and the geometry about the C=N double bond.

In the title compound, (2), (Fig. 1), 1H-indole ring is essentially planar, with a maximum deviation of -0.009 (1) Å for C8. The nine-membered indole ring makes dihedral angles of 54.75 (9) and 14.90 (9) °, respectively, with the phenyl ring (C9–C14) and the 2,5-dihydro-1,3-thiazole ring (S1/N4/C16–C18). The dihedral angle between the (C9–C14) and (S1/N4/C16–C18) rings is 69.15 (9)°.

In the molecule, intramolecular N—H···S hydrogen bonding interactions generate S(5) ring motifs. In the crystal, the two independent molecules are linked into a dimer by two N—H···O hydrogen bonds, forming a R₂²(10) ring motif (Fig. 2). The crystal structure, is further stabilized by intermolecular C—H···π [Cg1 and Cg2 are centroids of the S1/N4/C16–C18 and N1/C1/C6–C8 rings, respectively (Table 1)] and π–π interactions [Cg1···Cg2(x, -y, 1/2 + z) = 3.6791 (10) Å].

Related literature top

For the pharmaceutical features of 4-thiazolidinone derivatives, see: Bonde & Gaikwad (2004); Güzel et al. (2006); Küçükgüzel et al. (2002); Kline et al. (2008); Ottanà et al. (2005); Ulusoy (2002); Zhou et al. (2008); Çapan et al. (1999). Cg2 is the centroid of the N1/C1/C6–C8 ring.

Experimental top

A mixture of 4-allyl-1-[(5-fluoro-3-phenyl-1H-indol-2-yl)carbonyl]-3-τhiosemicarbazide (1) (0.0025 mol), ethyl bromoacetate (0.0025 mol) and fused sodium acetate (0.01 mol) in absolute ethanol (15 ml) was heated under reflux for 3 h. The solid thus obtained (2) was filtered, dried and purified by recrystallization from a mixture of ethanol: chloroform [Yield: 63.7%, m.p.: 535–538 K]. IR (KBr) ν = 3309, 3247 (N—H), 1716 (C=O), 1654 (C=O), 1608 (C=N) cm^-1; ¹H-NMR (DMSO-d₆, 500 MHz) δ = 4.05 (2H, s, S—CH₂), 4.24 (2H, s*, N—CH₂CH=CH₂), 5.12 (2H, s*, N—CH₂CH=CH₂), 5.81 (1H, s*, N—CH₂CH=CH₂), 7.11 (1H, dt, J = 9.1, 2.4 Hz, H6-indole), 7.15 (1H, d*, J = 9.3 Hz, H4-indole), 7.36 (1H, s*, 3-C₆H₅ (H4)-indole), 7.49–7.46 (5H, m, H7, 3-C₆H₅ (H2, H6, H3, H5)-indole), 9.78 (1H, s, CONH), 11.87 (1H, s, NH-indole) p.p.m. (* = broad). Analysis calculated for C₂₁H₁₇FN₄O₂S: C 61.75, H 4.20, N 13.72%. Found: C 61.84, H4.87, N 13.69%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the title molecule with the atom-numbering scheme and 30% probability displacement ellipsoids. Only the major occupancy component of the disorder part is depicted.
	Fig. 2. View of the two molecules linked into a dimer by two N—H···O hydrogen bonds [Symmetry code: (a) -1/2 + x,1/2 - y, -1/2 + z].

N'-[(2Z)-3-Allyl-4-oxo-1,3-thiazolidin-2-ylidene]-5-fluoro- 3-phenyl-1H-indole-2-carbohydrazide top

Crystal data top

C₂₁H₁₇FN₄O₂S	F(000) = 1696
M_r = 408.46	D_x = 1.390 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 28593 reflections
a = 21.9754 (6) Å	θ = 1.7–28.0°
b = 14.7215 (5) Å	µ = 0.20 mm⁻¹
c = 16.2447 (4) Å	T = 296 K
β = 132.022 (2)°	Prism, colourless
V = 3904.1 (2) Å³	0.48 × 0.45 × 0.41 mm
Z = 8

Data collection top

STOE IPDS2 diffractometer	4444 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3438 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.031
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.6°, θ_min = 1.9°
ω scans	h = −28→28
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→19
T_min = 0.910, T_max = 0.922	l = −21→21
27187 measured reflections

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0574P)² + 0.7834P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4444 reflections	Δρ_max = 0.21 e Å⁻³
302 parameters	Δρ_min = −0.18 e Å⁻³
4 restraints	Extinction correction: SHELXL, FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0009 (3)

Crystal data top

C₂₁H₁₇FN₄O₂S	V = 3904.1 (2) Å³
M_r = 408.46	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.9754 (6) Å	µ = 0.20 mm⁻¹
b = 14.7215 (5) Å	T = 296 K
c = 16.2447 (4) Å	0.48 × 0.45 × 0.41 mm
β = 132.022 (2)°

Data collection top

STOE IPDS2 diffractometer	4444 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3438 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.922	R_int = 0.031
27187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	4 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.21 e Å⁻³
4444 reflections	Δρ_min = −0.18 e Å⁻³
302 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.21369 (3)	0.12252 (4)	0.77932 (4)	0.0740 (2)
F1	0.17462 (7)	0.15524 (8)	0.14694 (8)	0.0831 (4)
O1	0.44729 (7)	0.05930 (11)	0.79608 (9)	0.0802 (5)
O2	0.31157 (12)	0.14689 (11)	1.08254 (13)	0.0975 (7)
N1	0.38666 (7)	0.08425 (9)	0.58683 (10)	0.0539 (4)
N2	0.33122 (8)	0.10877 (10)	0.75039 (10)	0.0607 (4)
N3	0.36940 (9)	0.11650 (10)	0.86108 (11)	0.0640 (5)
N4	0.35123 (10)	0.13330 (10)	0.98479 (12)	0.0683 (5)
C1	0.26040 (8)	0.11360 (10)	0.42564 (12)	0.0500 (4)
C2	0.20191 (9)	0.13246 (11)	0.31160 (13)	0.0572 (5)
C3	0.22958 (11)	0.13647 (12)	0.25772 (13)	0.0616 (5)
C4	0.31034 (11)	0.12236 (12)	0.30720 (14)	0.0650 (6)
C5	0.36848 (10)	0.10389 (12)	0.41841 (14)	0.0616 (5)
C6	0.34253 (9)	0.09967 (10)	0.47696 (12)	0.0516 (4)
C7	0.33549 (8)	0.08846 (10)	0.60763 (12)	0.0502 (4)
C8	0.25619 (8)	0.10495 (10)	0.50956 (12)	0.0482 (4)
C9	0.17981 (8)	0.10843 (10)	0.48911 (12)	0.0504 (4)
C10	0.15738 (10)	0.03640 (12)	0.51928 (14)	0.0632 (5)
C11	0.08451 (11)	0.03946 (15)	0.49644 (16)	0.0776 (7)
C12	0.03309 (11)	0.11353 (16)	0.44348 (17)	0.0802 (7)
C13	0.05436 (10)	0.18427 (15)	0.41220 (17)	0.0762 (7)
C14	0.12698 (10)	0.18184 (12)	0.43468 (15)	0.0627 (5)
C15	0.37596 (8)	0.08369 (11)	0.72532 (12)	0.0535 (5)
C16	0.32070 (11)	0.12386 (11)	0.87750 (13)	0.0594 (5)
C17	0.20908 (14)	0.13479 (16)	0.88526 (19)	0.0822 (8)
C18	0.29483 (14)	0.13926 (13)	0.99488 (17)	0.0741 (7)
C19	0.43942 (16)	0.13472 (19)	1.08020 (18)	0.0892 (9)
C20B	0.4660 (5)	0.2330 (6)	1.0835 (8)	0.146 (3)	0.513 (13)
C21B	0.5130 (6)	0.2848 (8)	1.1365 (7)	0.166 (4)	0.513 (13)
C21A	0.4594 (7)	0.2904 (7)	1.0986 (7)	0.105 (3)	0.487 (13)
C20A	0.4920 (5)	0.2117 (6)	1.1294 (7)	0.106 (3)	0.487 (13)
H2	0.14700	0.14170	0.27480	0.059 (4)*
H1	0.43840	0.07360	0.63550	0.061 (5)*
H5	0.42300	0.09450	0.45360	0.069 (5)*
H10	0.19150	−0.01390	0.55490	0.072 (5)*
H11	0.06990	−0.00890	0.51700	0.098 (7)*
H12	−0.01560	0.11540	0.42910	0.097 (7)*
H13	0.01970	0.23410	0.37570	0.103 (7)*
H14	0.14080	0.23020	0.41300	0.069 (5)*
H17A	0.17970	0.18980	0.87300	0.112 (8)*
H17B	0.18060	0.08350	0.88360	0.099 (7)*
H19A	0.4441 (17)	0.1087 (19)	1.132 (2)	0.113 (9)*
H19B	0.4668 (18)	0.086 (2)	1.066 (2)	0.132 (10)*
H20B	0.42670	0.25770	1.01300	0.1750*	0.513 (13)
H21C	0.55760	0.27220	1.21060	0.1990*	0.513 (13)
H21D	0.50830	0.34150	1.10740	0.1990*	0.513 (13)
H2A	0.27970	0.11990	0.69870	0.086 (6)*
H4	0.32490	0.12540	0.26510	0.076 (6)*
H20A	0.54860	0.20480	1.18250	0.1270*	0.487 (13)
H21A	0.40270	0.29620	1.04540	0.1260*	0.487 (13)
H21B	0.49230	0.34190	1.12940	0.1260*	0.487 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0723 (3)	0.0928 (4)	0.0657 (3)	0.0010 (2)	0.0498 (2)	−0.0014 (2)
F1	0.0882 (7)	0.1037 (8)	0.0487 (5)	0.0056 (6)	0.0422 (5)	0.0057 (5)
O1	0.0452 (6)	0.1385 (12)	0.0528 (6)	0.0108 (6)	0.0311 (5)	0.0155 (7)
O2	0.1405 (14)	0.1047 (11)	0.0858 (10)	0.0000 (10)	0.0916 (11)	−0.0059 (8)
N1	0.0420 (6)	0.0715 (8)	0.0493 (6)	0.0044 (5)	0.0310 (5)	0.0049 (6)
N2	0.0526 (7)	0.0862 (9)	0.0456 (6)	0.0083 (6)	0.0338 (6)	0.0055 (6)
N3	0.0659 (8)	0.0787 (9)	0.0473 (7)	0.0029 (7)	0.0379 (6)	0.0020 (6)
N4	0.0846 (10)	0.0724 (9)	0.0552 (8)	0.0019 (7)	0.0498 (8)	−0.0001 (6)
C1	0.0472 (7)	0.0554 (8)	0.0474 (7)	−0.0009 (6)	0.0317 (6)	−0.0003 (6)
C2	0.0520 (8)	0.0645 (9)	0.0481 (8)	0.0010 (6)	0.0306 (7)	−0.0003 (6)
C3	0.0692 (10)	0.0656 (10)	0.0458 (8)	−0.0002 (7)	0.0368 (8)	−0.0001 (7)
C4	0.0769 (10)	0.0737 (11)	0.0626 (10)	−0.0028 (8)	0.0542 (9)	−0.0028 (8)
C5	0.0610 (9)	0.0743 (10)	0.0642 (9)	0.0008 (7)	0.0480 (8)	0.0004 (8)
C6	0.0497 (7)	0.0585 (8)	0.0511 (7)	0.0010 (6)	0.0356 (6)	0.0005 (6)
C7	0.0460 (7)	0.0589 (8)	0.0510 (7)	0.0003 (6)	0.0347 (6)	0.0030 (6)
C8	0.0438 (6)	0.0548 (8)	0.0475 (7)	−0.0017 (5)	0.0312 (6)	0.0004 (6)
C9	0.0421 (7)	0.0614 (8)	0.0469 (7)	−0.0042 (6)	0.0295 (6)	−0.0026 (6)
C10	0.0545 (8)	0.0744 (11)	0.0623 (9)	−0.0029 (7)	0.0397 (8)	0.0082 (8)
C11	0.0587 (9)	0.1023 (14)	0.0775 (11)	−0.0106 (9)	0.0479 (9)	0.0122 (10)
C12	0.0487 (8)	0.1175 (16)	0.0786 (12)	−0.0027 (9)	0.0443 (9)	0.0071 (11)
C13	0.0537 (9)	0.0897 (13)	0.0840 (13)	0.0115 (8)	0.0456 (9)	0.0106 (10)
C14	0.0527 (8)	0.0656 (10)	0.0720 (10)	0.0006 (7)	0.0427 (8)	0.0041 (8)
C15	0.0456 (7)	0.0660 (9)	0.0496 (8)	−0.0036 (6)	0.0322 (7)	0.0023 (7)
C16	0.0733 (10)	0.0588 (9)	0.0541 (8)	0.0036 (7)	0.0459 (8)	0.0019 (7)
C17	0.0978 (14)	0.0875 (14)	0.0915 (14)	0.0088 (11)	0.0758 (13)	0.0004 (11)
C18	0.1055 (14)	0.0660 (11)	0.0765 (12)	0.0041 (9)	0.0715 (12)	0.0002 (8)
C19	0.0908 (15)	0.1127 (19)	0.0540 (11)	−0.0049 (13)	0.0443 (11)	−0.0017 (11)
C20B	0.095 (5)	0.109 (6)	0.070 (5)	−0.011 (4)	−0.012 (4)	0.013 (4)
C21B	0.093 (6)	0.140 (7)	0.150 (7)	−0.032 (5)	0.034 (5)	0.020 (5)
C21A	0.106 (6)	0.115 (6)	0.075 (4)	0.005 (4)	0.053 (4)	0.009 (4)
C20A	0.074 (4)	0.138 (6)	0.054 (4)	0.004 (4)	0.021 (3)	0.003 (4)

Geometric parameters (Å, º) top

S1—C16	1.747 (2)	C10—C11	1.382 (4)
S1—C17	1.800 (3)	C11—C12	1.380 (3)
F1—C3	1.3652 (19)	C12—C13	1.371 (4)
O1—C15	1.223 (2)	C13—C14	1.379 (4)
O2—C18	1.214 (3)	C17—C18	1.495 (4)
N1—C6	1.3639 (19)	C19—C20B	1.548 (10)
N1—C7	1.375 (3)	C19—C20A	1.422 (10)
N2—N3	1.3894 (19)	C20A—C21A	1.275 (14)
N2—C15	1.344 (3)	C20B—C21B	1.095 (15)
N3—C16	1.269 (4)	C2—H2	0.9300
N4—C16	1.393 (2)	C4—H4	0.9300
N4—C18	1.358 (4)	C5—H5	0.9300
N4—C19	1.462 (4)	C10—H10	0.9300
N1—H1	0.8600	C11—H11	0.9300
N2—H2A	0.8600	C12—H12	0.9300
C1—C6	1.407 (3)	C13—H13	0.9300
C1—C8	1.433 (3)	C14—H14	0.9300
C1—C2	1.405 (2)	C17—H17A	0.9700
C2—C3	1.361 (3)	C17—H17B	0.9700
C3—C4	1.389 (4)	C19—H19A	0.87 (3)
C4—C5	1.371 (2)	C19—H19B	1.06 (4)
C5—C6	1.400 (3)	C20A—H20A	0.9300
C7—C8	1.385 (2)	C20B—H20B	0.9300
C7—C15	1.475 (2)	C21A—H21A	0.9300
C8—C9	1.478 (3)	C21A—H21B	0.9300
C9—C10	1.390 (3)	C21B—H21C	0.9300
C9—C14	1.387 (3)	C21B—H21D	0.9300

S1···N2	2.925 (2)	C21B···S1^ix	3.605 (13)
S1···C11	3.634 (2)	C1···H14	3.0300
S1···C21Bⁱ	3.605 (13)	C1···H14ⁱⁱⁱ	3.0400
S1···H2A	2.5200	C2···H14	3.0900
F1···C10ⁱⁱ	3.369 (2)	C6···H14ⁱⁱⁱ	2.9500
F1···C20Bⁱⁱⁱ	3.284 (10)	C7···H14ⁱⁱⁱ	2.7800
F1···C16ⁱⁱⁱ	3.286 (2)	C7···H10	3.0600
F1···C21Aⁱⁱⁱ	3.082 (9)	C8···H2A	2.7600
F1···H11ⁱⁱ	2.8100	C8···H14ⁱⁱⁱ	2.9600
F1···H10ⁱⁱ	2.7300	C9···H2	3.0900
F1···H20Bⁱⁱⁱ	2.3700	C9···H2A	2.5400
F1···H21Aⁱⁱⁱ	2.4600	C10···H2A	2.6000
O1···N1	2.7205 (18)	C14···H2	2.9700
O1···N3	2.678 (3)	C15···H1^iv	3.0700
O1···N1^iv	2.789 (2)	C16···H20B	2.7000
O2···C17^v	3.336 (3)	C17···H21Cⁱ	2.8900
O1···H1^iv	1.9600	C18···H21A	3.0000
O1···H1	2.4900	C21B···H17A^ix	3.0800
O1···H19B^vi	2.74 (3)	H1···O1^iv	1.9600
O2···H4^vii	2.8000	H1···O1	2.4900
O2···H19A	2.51 (4)	H1···C15^iv	3.0700
O2···H17A^v	2.4800	H2···C14	2.9700
N1···O1	2.7205 (18)	H2···C9	3.0900
N1···O1^iv	2.789 (2)	H2···H12^x	2.5800
N2···C10	3.259 (2)	H2A···C9	2.5400
N2···S1	2.925 (2)	H2A···C10	2.6000
N2···C9	3.1904 (19)	H2A···C8	2.7600
N3···O1	2.678 (3)	H2A···S1	2.5200
N3···C20B	3.199 (10)	H4···O2^xi	2.8000
N3···C5^viii	3.379 (2)	H4···H20A^iv	2.5800
N4···C6^viii	3.433 (2)	H10···F1^viii	2.7300
N1···H14ⁱⁱⁱ	2.8000	H10···C7	3.0600
N3···H19B	2.52 (2)	H11···F1^viii	2.8100
N3···H20B	2.8000	H11···H12^xii	2.4600
N4···H21A	2.5500	H12···H11^xii	2.4600
C1···C14ⁱⁱⁱ	3.581 (2)	H12···H2^x	2.5800
C2···C14	3.413 (3)	H14···N1ⁱⁱⁱ	2.8000
C5···N3ⁱⁱ	3.379 (2)	H14···C1	3.0300
C5···C16ⁱⁱ	3.443 (2)	H14···C2	3.0900
C6···C14ⁱⁱⁱ	3.401 (2)	H14···C7ⁱⁱⁱ	2.7800
C6···N4ⁱⁱ	3.433 (2)	H14···C8ⁱⁱⁱ	2.9600
C6···C16ⁱⁱ	3.554 (2)	H14···C1ⁱⁱⁱ	3.0400
C9···N2	3.1904 (19)	H14···C6ⁱⁱⁱ	2.9500
C10···N2	3.259 (2)	H17A···O2^v	2.4800
C10···F1^viii	3.369 (2)	H17A···C21Bⁱ	3.0800
C11···S1	3.634 (2)	H17A···H21Cⁱ	2.2300
C14···C2	3.413 (3)	H19A···O2	2.51 (4)
C14···C6ⁱⁱⁱ	3.401 (2)	H19B···O1^vi	2.74 (3)
C14···C1ⁱⁱⁱ	3.581 (2)	H19B···N3	2.52 (2)
C16···C6^viii	3.554 (2)	H20A···H4^iv	2.5800
C16···F1ⁱⁱⁱ	3.286 (2)	H20B···C16	2.7000
C16···C5^viii	3.443 (2)	H20B···N3	2.8000
C17···O2^v	3.336 (3)	H20B···F1ⁱⁱⁱ	2.3700
C18···C21A	3.565 (14)	H21A···F1ⁱⁱⁱ	2.4600
C20B···N3	3.199 (10)	H21A···N4	2.5500
C20B···F1ⁱⁱⁱ	3.284 (10)	H21A···C18	3.0000
C21A···C18	3.565 (14)	H21C···H17A^ix	2.2300
C21A···F1ⁱⁱⁱ	3.082 (9)	H21C···C17^ix	2.8900

C16—S1—C17	91.66 (12)	O2—C18—C17	123.5 (3)
C6—N1—C7	109.39 (16)	N4—C18—C17	112.2 (2)
N3—N2—C15	118.97 (16)	N4—C19—C20A	127.5 (4)
N2—N3—C16	114.55 (17)	N4—C19—C20B	104.6 (4)
C16—N4—C18	116.3 (2)	C19—C20A—C21A	118.2 (10)
C16—N4—C19	120.9 (2)	C19—C20B—C21B	144.5 (10)
C18—N4—C19	122.7 (2)	C1—C2—H2	122.00
C7—N1—H1	125.00	C3—C2—H2	122.00
C6—N1—H1	125.00	C3—C4—H4	120.00
N3—N2—H2A	120.00	C5—C4—H4	120.00
C15—N2—H2A	121.00	C4—C5—H5	121.00
C2—C1—C6	119.25 (19)	C6—C5—H5	121.00
C2—C1—C8	133.4 (2)	C9—C10—H10	120.00
C6—C1—C8	107.31 (14)	C11—C10—H10	120.00
C1—C2—C3	116.7 (2)	C10—C11—H11	120.00
F1—C3—C2	118.3 (2)	C12—C11—H11	120.00
C2—C3—C4	124.70 (16)	C11—C12—H12	120.00
F1—C3—C4	117.0 (2)	C13—C12—H12	120.00
C3—C4—C5	119.7 (2)	C12—C13—H13	120.00
C4—C5—C6	117.4 (2)	C14—C13—H13	120.00
C1—C6—C5	122.36 (15)	C9—C14—H14	119.00
N1—C6—C1	107.82 (18)	C13—C14—H14	120.00
N1—C6—C5	129.8 (2)	S1—C17—H17A	110.00
C8—C7—C15	134.6 (2)	S1—C17—H17B	110.00
N1—C7—C15	115.70 (16)	C18—C17—H17A	110.00
N1—C7—C8	109.36 (15)	C18—C17—H17B	110.00
C1—C8—C9	124.76 (14)	H17A—C17—H17B	108.00
C7—C8—C9	129.06 (16)	N4—C19—H19A	104 (2)
C1—C8—C7	106.10 (18)	N4—C19—H19B	107.7 (16)
C8—C9—C10	120.79 (16)	C20B—C19—H19A	125.7 (19)
C8—C9—C14	120.69 (17)	C20B—C19—H19B	113 (2)
C10—C9—C14	118.5 (2)	H19A—C19—H19B	101 (3)
C9—C10—C11	120.10 (18)	C20A—C19—H19A	106.5 (19)
C10—C11—C12	120.8 (2)	C20A—C19—H19B	107 (2)
C11—C12—C13	119.4 (3)	C21A—C20A—H20A	121.00
C12—C13—C14	120.2 (2)	C19—C20A—H20A	121.00
C9—C14—C13	121.0 (2)	C21B—C20B—H20B	108.00
N2—C15—C7	116.83 (16)	C19—C20B—H20B	108.00
O1—C15—N2	122.24 (15)	C20A—C21A—H21A	120.00
O1—C15—C7	120.92 (19)	H21A—C21A—H21B	120.00
S1—C16—N4	111.7 (2)	C20A—C21A—H21B	120.00
N3—C16—N4	120.3 (2)	C20B—C21B—H21D	120.00
S1—C16—N3	128.04 (13)	H21C—C21B—H21D	120.00
S1—C17—C18	108.1 (2)	C20B—C21B—H21C	120.00
O2—C18—N4	124.3 (3)

C17—S1—C16—N4	−0.12 (14)	C2—C1—C6—C5	0.0 (2)
C17—S1—C16—N3	179.05 (17)	C1—C2—C3—F1	−179.58 (14)
C16—S1—C17—C18	−0.04 (16)	C1—C2—C3—C4	0.7 (3)
C6—N1—C7—C8	1.30 (17)	C2—C3—C4—C5	−0.8 (3)
C7—N1—C6—C5	178.52 (16)	F1—C3—C4—C5	179.53 (16)
C7—N1—C6—C1	−0.40 (17)	C3—C4—C5—C6	0.4 (3)
C6—N1—C7—C15	−173.18 (13)	C4—C5—C6—N1	−178.79 (16)
N3—N2—C15—O1	6.9 (3)	C4—C5—C6—C1	0.0 (2)
C15—N2—N3—C16	−167.60 (16)	C8—C7—C15—N2	−7.9 (3)
N3—N2—C15—C7	−171.95 (14)	N1—C7—C8—C9	175.12 (14)
N2—N3—C16—N4	−179.16 (14)	C15—C7—C8—C9	−11.9 (3)
N2—N3—C16—S1	1.7 (2)	C8—C7—C15—O1	173.20 (18)
C16—N4—C18—O2	179.34 (18)	C15—C7—C8—C1	171.37 (17)
C19—N4—C18—O2	0.5 (3)	N1—C7—C8—C1	−1.63 (17)
C18—N4—C16—S1	0.27 (19)	N1—C7—C15—N2	164.77 (15)
C18—N4—C19—C20B	−100.8 (5)	N1—C7—C15—O1	−14.1 (2)
C19—N4—C16—S1	179.10 (16)	C1—C8—C9—C10	122.17 (17)
C18—N4—C16—N3	−178.97 (16)	C1—C8—C9—C14	−54.8 (2)
C19—N4—C16—N3	−0.1 (3)	C7—C8—C9—C10	−54.0 (2)
C16—N4—C19—C20B	80.4 (5)	C7—C8—C9—C14	129.01 (18)
C16—N4—C18—C17	−0.3 (2)	C8—C9—C10—C11	−177.95 (16)
C19—N4—C18—C17	−179.11 (19)	C10—C9—C14—C13	0.9 (3)
C6—C1—C2—C3	−0.3 (2)	C14—C9—C10—C11	−0.9 (3)
C8—C1—C2—C3	179.17 (17)	C8—C9—C14—C13	177.94 (16)
C2—C1—C6—N1	179.01 (14)	C9—C10—C11—C12	0.1 (3)
C2—C1—C8—C9	4.9 (3)	C10—C11—C12—C13	0.8 (3)
C2—C1—C8—C7	−178.18 (17)	C11—C12—C13—C14	−0.8 (3)
C6—C1—C8—C7	1.37 (17)	C12—C13—C14—C9	−0.1 (3)
C6—C1—C8—C9	−175.56 (14)	S1—C17—C18—N4	0.2 (2)
C8—C1—C6—N1	−0.62 (17)	S1—C17—C18—O2	−179.46 (17)
C8—C1—C6—C5	−179.63 (15)	N4—C19—C20B—C21B	158 (2)

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, −y, z−1/2; (iii) −x+1/2, −y+1/2, −z+1; (iv) −x+1, y, −z+3/2; (v) −x+1/2, −y+1/2, −z+2; (vi) −x+1, −y, −z+2; (vii) x, y, z+1; (viii) x, −y, z+1/2; (ix) x+1/2, −y+1/2, z+1/2; (x) −x, y, −z+1/2; (xi) x, y, z−1; (xii) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^iv	0.86	1.96	2.789 (2)	161
N2—H2A···S1	0.86	2.52	2.925 (2)	110
C17—H17A···O2^v	0.97	2.48	3.336 (3)	147
C19—H19A···O2	0.87 (3)	2.51 (4)	2.841 (5)	103 (3)
C20B—H20B···F1ⁱⁱⁱ	0.93	2.37	3.284 (10)	168
C14—H14···Cg2ⁱⁱⁱ	0.93	2.66	3.371 (2)	134

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇FN₄O₂S
M_r	408.46
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	21.9754 (6), 14.7215 (5), 16.2447 (4)
β (°)	132.022 (2)
V (Å³)	3904.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.48 × 0.45 × 0.41

Data collection
Diffractometer	STOE IPDS2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.910, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	27187, 4444, 3438
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.04
No. of reflections	4444
No. of parameters	302
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.96	2.789 (2)	161
N2—H2A···S1	0.86	2.52	2.925 (2)	110
C17—H17A···O2ⁱⁱ	0.97	2.48	3.336 (3)	147
C19—H19A···O2	0.87 (3)	2.51 (4)	2.841 (5)	103 (3)
C20B—H20B···F1ⁱⁱⁱ	0.93	2.37	3.284 (10)	168
C14—H14···Cg2ⁱⁱⁱ	0.93	2.66	3.371 (2)	134

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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Volume 65| Part 5| May 2009| Pages o1009-o1010

doi:10.1107/S1600536809012677

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

N′-[(2Z)-3-Allyl-4-oxo-1,3-thia­zolidin-2-yl­­idene]-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[(2Z)-3-Allyl-4-oxo-1,3-thiazolidin-2-ylidene]-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide