1-[2-Oxo-5-(trifluoro­meth­oxy)indolin-3-yl­idene]-4-[4-(trifluoro­methyl)­phen­yl]thio­semicarbazide

Pervez, H.; Iqbal, M.S.; Saira, N.; Yaqub, M.; Tahir, M.N.

doi:10.1107/S1600536810023494

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1749

doi:10.1107/S1600536810023494

Open

access

1-[2-Oxo-5-(trifluoromethoxy)indolin-3-ylidene]-4-[4-(trifluoromethyl)phenyl]thiosemicarbazide

Humayun Pervez,^a Mohammad S. Iqbal,^b Naveeda Saira,^a Muhammad Yaqub ^a and M. Nawaz Tahir ^c ^*

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, ^bDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 13 June 2010; accepted 17 June 2010; online 23 June 2010)

In the title compound, C₁₇H₁₀F₆N₄O₂S, an intramolecular N—H⋯N hydrogen bonds forms an S(5) ring whereas N—H⋯O and C—H⋯S interactions complete S(6) ring motifs. The dihedral angle between the fused ring system and the phenyl ring is 6.68 (8)°. In the crystal, the molecules are dimerized due to N—H⋯O interactions. π–π interactions are present between the benzene rings [centroid–centroid distance = 3.6913 (15) Å] and between the five membered ring and the trifluoromethyl)phenyl ring [centroids–centroid distance = 3.7827 (16) Å]. One of the trifluoromethoxy F atoms is disordered over two sites with occupancy ratio of 0.76 (3):0.24 (3). The F atoms of the p-trifluoromethyl substituent are disordered over three sets of sites with an occupancy ratio of 0.70 (2):0.152 (11):0.147 (13).

Related literature

For background to the synthesis, see: Pervez et al. (2009 , 2010b ,c ). For a related structure, see: Pervez et al. (2010a ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₀F₆N₄O₂S
M_r = 448.35
Triclinic, $[P \overline 1]$
a = 7.5452 (11) Å
b = 8.3177 (13) Å
c = 16.048 (2) Å
α = 104.452 (6)°
β = 94.752 (7)°
γ = 103.606 (7)°
V = 937.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.942, T_max = 0.952
13964 measured reflections
3351 independent reflections
2191 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.113
S = 1.02
3351 reflections
302 parameters
11 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.24 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	1.98	2.829 (3)	168
N3—H3A⋯O1	0.86	2.01	2.716 (3)	138
N4—H4A⋯N2	0.86	2.19	2.627 (3)	111
C12—H12⋯S1	0.93	2.56	3.210 (3)	128
Symmetry code: (i) -x+2, -y+3, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023494/si2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023494/si2270Isup2.hkl

checkCIF report

Comment top

In continuation of our earlier studies on the synthesis of biologically important N⁴-arylsubstituted isatins-3-thiosemicarbazones (Pervez et al., 2009, 2010b, 2010c), here we report the synthesis and crystal structure of the title compound (I, Fig. 1).

The crystal structure of (II) i.e. 4-(5-chloro-2-methylphenyl)-1-(2-oxo-5-(trifluoromethoxy) indolin-3-ylidene) thiosemicarbazide has been published (Pervez et al., 2010a). The title compound (I) differs from (II) due to the presence of trifluoromethyl group at position-4 instead of methyl and chloro functions at position-2 and -5, respectively, of the phenyl ring substituted at N⁴- of the thiosemicarbazone moiety.

In (I), the 2-oxoindolin A (C1–C8/N1/O1), thiosemicarbazone moiety B (N2/N3/C10/S1/N4) and the phenyl ring C (C11—C16) having p-trifluoromethyl function are planar with r. m. s. deviations of 0.0402, 0.0184 and 0.0119 Å, respectively. The dihedral angle between A/B, A/C and B/C is 6.78 (9), 6.68 (8) and 13.42 (10)°, respectively. Due to intramolecular H-bondings (Table 1, Fig. 1), one S(5) and two S(6) (Bernstein et al., 1995) ring motifs are formed. The molecules are dimerized (Fig. 2) due to intermolecular H-bonding of N—H···O type with R₂²(8) ring motifs. The dimers are interlinked through C—H···F type of H-bonding. There exist π···π interaction at a distance of 3.6913 (15) Å between the centroids of phenyl rings (C2—C7) and (C11—C16). Similarly, π···π interaction between the centroids of the heterocyclic ring (N1/C1/C8/C7/C2) and the phenyl ring (C11—C16) is 3.7827 (16) Å.

One of the F-atom of trifluoromethoxy group is disordered over two set of sites with occupancy ratio of 0.76 (3):0.24 (3). The F-atoms of p-trifluoromethyl function are disordered over three groups with occupancy ratio of 0.70 (2):0.152 (11):0.147 (13).

Related literature top

For background to the synthesis, see: Pervez et al. (2009, 2010b,c). For a related structure, see: Pervez et al. (2010a). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

4-(4-Trifluoromethylphenyl)thiosemicarbazide (0.94 g, 4.0 mmol) dissolved in ethanol (10 ml) was added to a hot solution of 5-(trifluoromethoxy)indolin-2,3-dione (0.92 g, 4.0 mmol) in 50% aqueous ethanol (20 ml) containing a catalytic quantity of glacial acetic acid. The reaction mixture was then refluxed for 2 h. The yellow powder formed during refluxing was collected by suction filtration. Thorough washing with hot aqueous ethanol afforded the title compound (I) in pure form (1.34 g, 75%), m.p. 513 K. The yellow crystals of the title compound for x-ray analysis were obtained from the solution of ethyl acetate-petroleum ether (2:5) at room temperature by diffusion method.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The dotted lines indicate the intra-molecular H-bondings. Only the majority group of F-atoms are shown for clarity.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules are dimerized and interlinked.

1-[2-Oxo-5-(trifluoromethoxy)indolin-3-ylidene]-4-[4- (trifluoromethyl)phenyl]thiosemicarbazide top

Crystal data top

C₁₇H₁₀F₆N₄O₂S	Z = 2
M_r = 448.35	F(000) = 452
Triclinic, P1	D_x = 1.589 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5452 (11) Å	Cell parameters from 2191 reflections
b = 8.3177 (13) Å	θ = 2.6–25.3°
c = 16.048 (2) Å	µ = 0.25 mm⁻¹
α = 104.452 (6)°	T = 296 K
β = 94.752 (7)°	Prism, yellow
γ = 103.606 (7)°	0.32 × 0.24 × 0.22 mm
V = 937.1 (2) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3351 independent reflections
Radiation source: fine-focus sealed tube	2191 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 8.2 pixels mm^-1	θ_max = 25.3°, θ_min = 2.6°
ω scans	h = −9→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
T_min = 0.942, T_max = 0.952	l = −19→19
13964 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0501P)² + 0.1774P] where P = (F_o² + 2F_c²)/3
3351 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 0.24 e Å⁻³
11 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₀F₆N₄O₂S	γ = 103.606 (7)°
M_r = 448.35	V = 937.1 (2) Å³
Triclinic, P1	Z = 2
a = 7.5452 (11) Å	Mo Kα radiation
b = 8.3177 (13) Å	µ = 0.25 mm⁻¹
c = 16.048 (2) Å	T = 296 K
α = 104.452 (6)°	0.32 × 0.24 × 0.22 mm
β = 94.752 (7)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3351 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2191 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.952	R_int = 0.045
13964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	11 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.02	Δρ_max = 0.24 e Å⁻³
3351 reflections	Δρ_min = −0.24 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 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	0.59532 (11)	0.73584 (9)	0.47879 (5)	0.0642 (3)
F1A	0.786 (2)	1.3866 (16)	−0.0060 (4)	0.113 (2)	0.76 (3)
F2	0.5218 (3)	1.2388 (3)	−0.08045 (11)	0.1050 (9)
F3	0.6805 (3)	1.1403 (3)	−0.00024 (13)	0.1212 (11)
F4A	0.1431 (7)	−0.0888 (4)	0.1803 (6)	0.091 (2)	0.70 (2)
F5A	−0.0432 (14)	−0.0301 (5)	0.0936 (4)	0.110 (3)	0.70 (2)
F6A	−0.1071 (10)	−0.0475 (4)	0.2190 (6)	0.107 (2)	0.70 (2)
O1	0.8661 (2)	1.2725 (2)	0.48040 (11)	0.0593 (7)
O2	0.5300 (3)	1.3270 (2)	0.05819 (12)	0.0636 (7)
N1	0.8671 (3)	1.4593 (3)	0.39550 (13)	0.0496 (7)
N2	0.5938 (3)	1.0294 (2)	0.32681 (12)	0.0455 (7)
N3	0.6239 (3)	0.9659 (3)	0.39467 (13)	0.0512 (7)
N4	0.4128 (3)	0.7152 (2)	0.32184 (13)	0.0496 (7)
C1	0.8144 (3)	1.3071 (3)	0.41361 (16)	0.0466 (9)
C2	0.7898 (3)	1.4494 (3)	0.31108 (16)	0.0446 (8)
C3	0.8150 (3)	1.5752 (3)	0.26892 (17)	0.0536 (9)
C4	0.7282 (3)	1.5321 (3)	0.18411 (18)	0.0565 (10)
C5	0.6218 (3)	1.3664 (3)	0.14478 (16)	0.0502 (9)
C6	0.5918 (3)	1.2393 (3)	0.18672 (15)	0.0469 (8)
C7	0.6774 (3)	1.2829 (3)	0.27192 (15)	0.0414 (8)
C8	0.6832 (3)	1.1869 (3)	0.33561 (15)	0.0423 (8)
C9	0.6260 (5)	1.2776 (5)	−0.0049 (2)	0.0792 (14)
C10	0.5363 (3)	0.8008 (3)	0.39415 (15)	0.0454 (8)
C11	0.3131 (3)	0.5405 (3)	0.29085 (16)	0.0446 (8)
C12	0.2921 (4)	0.4258 (3)	0.34125 (17)	0.0564 (9)
C13	0.1977 (4)	0.2559 (3)	0.30334 (18)	0.0588 (10)
C14	0.1225 (3)	0.1981 (3)	0.21696 (18)	0.0523 (9)
C15	0.1373 (3)	0.3133 (3)	0.16787 (18)	0.0579 (9)
C16	0.2315 (3)	0.4828 (3)	0.20459 (17)	0.0543 (9)
C17	0.0301 (5)	0.0118 (4)	0.1773 (2)	0.0696 (13)
F6B	−0.128 (2)	−0.001 (2)	0.1300 (17)	0.084 (4)	0.152 (11)
F6C	0.055 (4)	−0.041 (2)	0.0970 (13)	0.084 (4)	0.147 (13)
F4C	−0.1510 (19)	−0.023 (3)	0.1788 (19)	0.084 (4)	0.147 (13)
F1B	0.727 (4)	1.432 (4)	−0.0021 (14)	0.113 (2)	0.24 (3)
F4B	−0.023 (4)	−0.061 (2)	0.2404 (11)	0.084 (4)	0.152 (11)
F5B	0.143 (3)	−0.071 (2)	0.138 (2)	0.084 (4)	0.152 (11)
F5C	0.096 (3)	−0.087 (2)	0.2206 (18)	0.084 (4)	0.147 (13)
H3A	0.70052	1.03089	0.43980	0.0615*
H15	0.08340	0.27634	0.10976	0.0695*
H16	0.24060	0.55988	0.17100	0.0652*
H4	0.74155	1.61460	0.15357	0.0679*
H4A	0.39115	0.77794	0.28900	0.0595*
H6	0.51745	1.12914	0.15911	0.0563*
H12	0.34120	0.46323	0.40001	0.0676*
H13	0.18465	0.17879	0.33702	0.0704*
H1	0.93911	1.55096	0.43112	0.0594*
H3	0.88805	1.68594	0.29640	0.0643*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0831 (5)	0.0563 (5)	0.0494 (4)	0.0101 (4)	−0.0045 (4)	0.0202 (3)
F1A	0.091 (5)	0.147 (5)	0.0733 (15)	−0.016 (4)	0.027 (2)	0.021 (2)
F2	0.1342 (17)	0.1161 (16)	0.0486 (11)	0.0132 (13)	−0.0175 (11)	0.0230 (11)
F3	0.178 (2)	0.136 (2)	0.0743 (14)	0.0873 (18)	0.0274 (13)	0.0277 (13)
F4A	0.105 (3)	0.0511 (18)	0.113 (5)	0.0310 (18)	0.026 (3)	0.004 (2)
F5A	0.134 (8)	0.064 (2)	0.089 (3)	−0.012 (3)	−0.033 (4)	−0.002 (2)
F6A	0.086 (4)	0.0480 (19)	0.175 (6)	−0.009 (2)	0.059 (4)	0.023 (3)
O1	0.0684 (12)	0.0488 (11)	0.0473 (11)	−0.0009 (9)	−0.0120 (9)	0.0116 (9)
O2	0.0700 (12)	0.0651 (13)	0.0498 (12)	0.0093 (10)	−0.0072 (10)	0.0186 (10)
N1	0.0535 (12)	0.0370 (12)	0.0440 (13)	−0.0028 (10)	−0.0063 (10)	0.0041 (10)
N2	0.0528 (12)	0.0378 (12)	0.0411 (12)	0.0051 (10)	0.0037 (9)	0.0097 (10)
N3	0.0637 (13)	0.0373 (12)	0.0429 (12)	0.0005 (10)	−0.0051 (10)	0.0099 (10)
N4	0.0601 (13)	0.0369 (12)	0.0454 (13)	0.0016 (10)	−0.0052 (10)	0.0149 (10)
C1	0.0455 (14)	0.0414 (15)	0.0454 (16)	0.0046 (12)	−0.0004 (12)	0.0074 (12)
C2	0.0440 (13)	0.0374 (14)	0.0451 (15)	0.0033 (11)	0.0033 (11)	0.0063 (12)
C3	0.0578 (16)	0.0373 (14)	0.0562 (18)	0.0004 (12)	0.0018 (13)	0.0098 (13)
C4	0.0645 (17)	0.0438 (16)	0.0597 (18)	0.0063 (13)	0.0051 (14)	0.0204 (14)
C5	0.0522 (15)	0.0489 (16)	0.0448 (16)	0.0082 (13)	−0.0023 (12)	0.0125 (13)
C6	0.0493 (14)	0.0387 (14)	0.0456 (15)	0.0047 (11)	0.0006 (12)	0.0077 (12)
C7	0.0415 (13)	0.0363 (13)	0.0399 (14)	0.0037 (11)	0.0015 (10)	0.0067 (11)
C8	0.0432 (13)	0.0363 (14)	0.0402 (14)	0.0036 (11)	0.0006 (10)	0.0061 (11)
C9	0.102 (3)	0.077 (2)	0.051 (2)	0.007 (2)	−0.0007 (19)	0.0236 (18)
C10	0.0521 (14)	0.0402 (14)	0.0410 (15)	0.0097 (12)	0.0049 (12)	0.0092 (12)
C11	0.0472 (14)	0.0373 (14)	0.0460 (15)	0.0052 (11)	0.0046 (11)	0.0120 (12)
C12	0.0705 (17)	0.0460 (16)	0.0491 (16)	0.0049 (14)	0.0042 (13)	0.0185 (13)
C13	0.0663 (17)	0.0435 (16)	0.066 (2)	0.0047 (14)	0.0098 (15)	0.0235 (14)
C14	0.0462 (14)	0.0398 (15)	0.0637 (18)	0.0012 (12)	0.0083 (13)	0.0111 (14)
C15	0.0589 (16)	0.0521 (17)	0.0497 (16)	−0.0004 (13)	−0.0030 (13)	0.0086 (14)
C16	0.0620 (16)	0.0464 (16)	0.0490 (16)	0.0010 (13)	−0.0004 (13)	0.0186 (13)
C17	0.069 (2)	0.0494 (18)	0.081 (3)	0.0013 (17)	0.0123 (19)	0.0147 (17)
F6B	0.080 (6)	0.053 (4)	0.097 (8)	0.003 (3)	0.026 (5)	−0.007 (4)
F6C	0.080 (6)	0.053 (4)	0.097 (8)	0.003 (3)	0.026 (5)	−0.007 (4)
F4C	0.080 (6)	0.053 (4)	0.097 (8)	0.003 (3)	0.026 (5)	−0.007 (4)
F1B	0.091 (5)	0.147 (5)	0.0733 (15)	−0.016 (4)	0.027 (2)	0.021 (2)
F4B	0.080 (6)	0.053 (4)	0.097 (8)	0.003 (3)	0.026 (5)	−0.007 (4)
F5B	0.080 (6)	0.053 (4)	0.097 (8)	0.003 (3)	0.026 (5)	−0.007 (4)
F5C	0.080 (6)	0.053 (4)	0.097 (8)	0.003 (3)	0.026 (5)	−0.007 (4)

Geometric parameters (Å, º) top

S1—C10	1.648 (3)	N3—H3A	0.8600
F1A—C9	1.333 (15)	N4—H4A	0.8600
F1B—C9	1.32 (3)	C1—C8	1.500 (3)
F2—C9	1.311 (4)	C2—C7	1.399 (4)
F3—C9	1.318 (5)	C2—C3	1.367 (4)
F4A—C17	1.334 (6)	C3—C4	1.381 (4)
F4B—C17	1.346 (18)	C4—C5	1.380 (4)
F4C—C17	1.332 (17)	C5—C6	1.375 (4)
F5A—C17	1.336 (7)	C6—C7	1.384 (3)
F5B—C17	1.32 (2)	C7—C8	1.449 (3)
F5C—C17	1.35 (2)	C11—C16	1.383 (4)
F6A—C17	1.342 (8)	C11—C12	1.387 (4)
F6B—C17	1.33 (2)	C12—C13	1.378 (4)
F6C—C17	1.30 (2)	C13—C14	1.372 (4)
O1—C1	1.233 (3)	C14—C15	1.376 (4)
O2—C9	1.331 (4)	C14—C17	1.489 (4)
O2—C5	1.423 (3)	C15—C16	1.373 (4)
N1—C1	1.346 (4)	C3—H3	0.9300
N1—C2	1.405 (3)	C4—H4	0.9300
N2—N3	1.349 (3)	C6—H6	0.9300
N2—C8	1.291 (3)	C12—H12	0.9300
N3—C10	1.374 (4)	C13—H13	0.9300
N4—C10	1.348 (3)	C15—H15	0.9300
N4—C11	1.410 (3)	C16—H16	0.9300
N1—H1	0.8600

S1···N1ⁱ	3.524 (3)	N3···O1	2.716 (3)
S1···C12	3.210 (3)	N4···N2	2.627 (3)
S1···C13ⁱⁱ	3.687 (3)	N2···H4A	2.1900
S1···C1ⁱⁱⁱ	3.652 (3)	C1···C13^vi	3.568 (4)
S1···C12ⁱⁱ	3.597 (3)	C1···S1ⁱⁱⁱ	3.652 (3)
S1···H12	2.5600	C3···F6A^xii	3.362 (5)
S1···H12ⁱⁱ	2.9300	C3···F4B^xii	3.147 (18)
S1···H13ⁱⁱ	3.1000	C3···C16^vi	3.579 (3)
F1A···C4	3.097 (8)	C3···C10^xi	3.558 (3)
F1A···F5B^iv	3.12 (3)	C4···F6A^xii	3.309 (5)
F1B···C4	2.89 (2)	C4···F4B^xii	3.316 (19)
F2···F4C^v	3.01 (2)	C4···F1A	3.097 (8)
F2···F6B^v	3.071 (17)	C4···F1B	2.89 (2)
F3···C6	3.080 (3)	C5···C16^xi	3.446 (3)
F3···F6B^vi	3.06 (2)	C6···F6B^vi	3.270 (17)
F3···F5B^iv	2.68 (3)	C6···C14^xi	3.562 (3)
F3···F6C^iv	2.78 (3)	C6···F4C^vi	3.23 (2)
F4B···C3^vii	3.147 (18)	C6···F3	3.080 (3)
F4B···C4^vii	3.316 (19)	C7···F4C^vi	3.22 (2)
F4C···C8^viii	3.21 (3)	C7···C12^xi	3.550 (4)
F4C···C6^viii	3.23 (2)	C8···F6A^vi	3.151 (8)
F4C···C7^viii	3.22 (2)	C8···F4C^vi	3.21 (3)
F4C···N2^viii	3.19 (2)	C9···F5B^iv	3.28 (3)
F4C···F2^v	3.01 (2)	C10···C3ⁱ	3.558 (3)
F5B···F1A^iv	3.12 (3)	C12···C7ⁱ	3.550 (4)
F5B···F3^iv	2.68 (3)	C12···S1	3.210 (3)
F5B···C9^iv	3.28 (3)	C12···S1ⁱⁱ	3.597 (3)
F6A···C3^vii	3.362 (5)	C12···N1^viii	3.447 (4)
F6A···C8^viii	3.151 (8)	C13···S1ⁱⁱ	3.687 (3)
F6A···N2^viii	3.045 (8)	C13···C1^viii	3.568 (4)
F6A···C4^vii	3.309 (5)	C14···C6ⁱ	3.562 (3)
F6B···F2^v	3.071 (17)	C16···C5ⁱ	3.446 (3)
F6B···C6^viii	3.270 (17)	C16···C3^viii	3.579 (3)
F6B···F3^viii	3.06 (2)	C1···H1^x	2.7900
F6C···F3^iv	2.78 (3)	C1···H3A	2.4100
F1A···H16^ix	2.7900	C10···H12	2.8800
F1B···H4	2.5600	H1···O1^x	1.9800
F1B···H16^ix	2.7600	H1···C1^x	2.7900
F4A···H13	2.8500	H3···F4B^xii	2.4600
F4B···H3^vii	2.4600	H3···F6A^xii	2.7900
F4B···H4^vii	2.8000	H3···F5C^xii	2.7500
F4B···H13	2.3300	H3A···C1	2.4100
F4C···H4^vii	2.8500	H3A···O1	2.0100
F5A···H15	2.4400	H4···F1B	2.5600
F5B···H6ⁱ	2.8700	H4···F6A^xii	2.6700
F5C···H13	2.4200	H4···F4B^xii	2.8000
F5C···H3^vii	2.7500	H4···F4C^xii	2.8500
F6A···H3^vii	2.7900	H4A···N2	2.1900
F6A···H13	2.7500	H4A···H16	2.2600
F6A···H4^vii	2.6700	H6···F5B^xi	2.8700
F6B···H15	2.5900	H12···C10	2.8800
F6C···H15	2.5500	H12···S1	2.5600
O1···N2	3.017 (3)	H12···S1ⁱⁱ	2.9300
O1···N1^x	2.829 (3)	H13···F6A	2.7500
O1···N3	2.716 (3)	H13···F4A	2.8500
O1···H3A	2.0100	H13···S1ⁱⁱ	3.1000
O1···H1^x	1.9800	H13···F4B	2.3300
N1···O1^x	2.829 (3)	H13···F5C	2.4200
N1···C12^vi	3.447 (4)	H15···F6C	2.5500
N1···S1^xi	3.524 (3)	H15···F6B	2.5900
N2···O1	3.017 (3)	H15···F5A	2.4400
N2···N4	2.627 (3)	H16···F1A^ix	2.7900
N2···F4C^vi	3.19 (2)	H16···F1B^ix	2.7600
N2···F6A^vi	3.045 (8)	H16···H4A	2.2600

C5—O2—C9	115.9 (2)	N4—C11—C16	116.8 (2)
C1—N1—C2	111.5 (2)	N4—C11—C12	124.2 (2)
N3—N2—C8	116.3 (2)	C11—C12—C13	119.3 (2)
N2—N3—C10	122.3 (2)	C12—C13—C14	121.4 (2)
C10—N4—C11	131.0 (2)	C13—C14—C15	119.2 (2)
C2—N1—H1	124.00	C13—C14—C17	119.8 (2)
C1—N1—H1	124.00	C15—C14—C17	121.0 (3)
N2—N3—H3A	119.00	C14—C15—C16	120.1 (3)
C10—N3—H3A	119.00	C11—C16—C15	120.9 (2)
C10—N4—H4A	114.00	F4A—C17—C14	113.1 (4)
C11—N4—H4A	114.00	F4A—C17—F5A	105.1 (6)
O1—C1—N1	126.9 (2)	F4A—C17—F6A	104.2 (4)
N1—C1—C8	106.3 (2)	F5C—C17—C14	111.4 (10)
O1—C1—C8	126.8 (2)	F6B—C17—C14	108.0 (8)
N1—C2—C7	109.2 (2)	F6C—C17—C14	112.3 (9)
N1—C2—C3	128.5 (2)	F4B—C17—F5B	107.0 (15)
C3—C2—C7	122.3 (2)	F4B—C17—F6B	103.6 (16)
C2—C3—C4	117.7 (2)	F4C—C17—F5C	106.9 (15)
C3—C4—C5	119.9 (2)	F4C—C17—F6C	107.7 (18)
C4—C5—C6	123.2 (2)	F5B—C17—F6B	116.9 (16)
O2—C5—C4	118.6 (2)	F5C—C17—F6C	106.5 (15)
O2—C5—C6	118.1 (2)	F5A—C17—F6A	106.0 (6)
C5—C6—C7	116.9 (2)	F5A—C17—C14	115.0 (3)
C2—C7—C8	106.7 (2)	F6A—C17—C14	112.5 (4)
C6—C7—C8	133.3 (2)	F4B—C17—C14	109.2 (8)
C2—C7—C6	120.0 (2)	F4C—C17—C14	111.7 (12)
C1—C8—C7	106.2 (2)	F5B—C17—C14	111.7 (9)
N2—C8—C1	127.0 (2)	C2—C3—H3	121.00
N2—C8—C7	126.9 (2)	C4—C3—H3	121.00
F1A—C9—F3	100.9 (7)	C3—C4—H4	120.00
F1A—C9—F2	109.0 (4)	C5—C4—H4	120.00
F1B—C9—O2	97.3 (12)	C5—C6—H6	122.00
F1A—C9—O2	117.2 (5)	C7—C6—H6	122.00
F2—C9—F3	107.5 (3)	C11—C12—H12	120.00
F2—C9—O2	109.1 (3)	C13—C12—H12	120.00
F1B—C9—F2	100.0 (11)	C12—C13—H13	119.00
F3—C9—O2	112.6 (3)	C14—C13—H13	119.00
F1B—C9—F3	128.7 (14)	C14—C15—H15	120.00
S1—C10—N3	117.20 (18)	C16—C15—H15	120.00
S1—C10—N4	129.66 (19)	C11—C16—H16	120.00
N3—C10—N4	113.1 (2)	C15—C16—H16	120.00
C12—C11—C16	119.0 (2)

C9—O2—C5—C4	88.2 (3)	C2—C3—C4—C5	−0.5 (4)
C9—O2—C5—C6	−95.3 (3)	C3—C4—C5—O2	178.3 (2)
C5—O2—C9—F1A	−58.3 (7)	C3—C4—C5—C6	1.9 (4)
C5—O2—C9—F2	177.3 (2)	O2—C5—C6—C7	−177.7 (2)
C5—O2—C9—F3	58.1 (4)	C4—C5—C6—C7	−1.3 (4)
C2—N1—C1—O1	176.1 (2)	C5—C6—C7—C2	−0.6 (3)
C2—N1—C1—C8	−2.7 (3)	C5—C6—C7—C8	−178.4 (2)
C1—N1—C2—C3	−178.1 (2)	C2—C7—C8—N2	177.6 (2)
C1—N1—C2—C7	1.2 (3)	C2—C7—C8—C1	−2.6 (3)
C8—N2—N3—C10	179.4 (2)	C6—C7—C8—N2	−4.4 (4)
N3—N2—C8—C1	−1.0 (4)	C6—C7—C8—C1	175.4 (3)
N3—N2—C8—C7	178.8 (2)	N4—C11—C12—C13	−177.5 (3)
N2—N3—C10—S1	176.33 (19)	C16—C11—C12—C13	2.9 (4)
N2—N3—C10—N4	−3.3 (3)	N4—C11—C16—C15	177.6 (2)
C11—N4—C10—S1	−8.8 (4)	C12—C11—C16—C15	−2.7 (4)
C11—N4—C10—N3	170.8 (2)	C11—C12—C13—C14	−0.6 (4)
C10—N4—C11—C12	15.8 (4)	C12—C13—C14—C15	−1.9 (4)
C10—N4—C11—C16	−164.5 (2)	C12—C13—C14—C17	176.8 (3)
O1—C1—C8—N2	4.2 (4)	C13—C14—C15—C16	2.1 (4)
O1—C1—C8—C7	−175.6 (2)	C17—C14—C15—C16	−176.6 (3)
N1—C1—C8—N2	−176.9 (2)	C13—C14—C17—F4A	−61.2 (5)
N1—C1—C8—C7	3.3 (3)	C13—C14—C17—F5A	178.1 (6)
N1—C2—C3—C4	177.7 (2)	C13—C14—C17—F6A	56.5 (5)
C7—C2—C3—C4	−1.5 (4)	C15—C14—C17—F4A	117.4 (5)
N1—C2—C7—C6	−177.3 (2)	C15—C14—C17—F5A	−3.3 (6)
N1—C2—C7—C8	1.0 (3)	C15—C14—C17—F6A	−124.9 (4)
C3—C2—C7—C6	2.1 (4)	C14—C15—C16—C11	0.2 (4)
C3—C2—C7—C8	−179.7 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^x	0.8600	1.9800	2.829 (3)	168.00
N3—H3A···O1	0.8600	2.0100	2.716 (3)	138.00
N4—H4A···N2	0.8600	2.1900	2.627 (3)	111.00
C12—H12···S1	0.9300	2.5600	3.210 (3)	128.00
C15—H15···F5A	0.9300	2.4400	2.763 (6)	100.00

Symmetry code: (x) −x+2, −y+3, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀F₆N₄O₂S
M_r	448.35
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5452 (11), 8.3177 (13), 16.048 (2)
α, β, γ (°)	104.452 (6), 94.752 (7), 103.606 (7)
V (Å³)	937.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.32 × 0.24 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.942, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	13964, 3351, 2191
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.113, 1.02
No. of reflections	3351
No. of parameters	302
No. of restraints	11
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.8600	1.9800	2.829 (3)	168.00
N3—H3A···O1	0.8600	2.0100	2.716 (3)	138.00
N4—H4A···N2	0.8600	2.1900	2.627 (3)	111.00
C12—H12···S1	0.9300	2.5600	3.210 (3)	128.00
C15—H15···F5A	0.9300	2.4400	2.763 (6)	100.00

Symmetry code: (i) −x+2, −y+3, −z+1.

Acknowledgements

This work was supported by the Higher Education Commission (HEC), Pakistan (project No. 20–873/R&D/07/452).

References

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
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Pervez, H., Iqbal, M. S., Saira, N., Yaqub, M. & Tahir, M. N. (2010a). Acta Cryst. E66, o1169–o1170. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pervez, H., Manzoor, N., Yaqub, M., Khan, A., Khan, K. M., Nasim, F. H. & Choudhary, M. I. (2010b). Lett. Drug Des. Discov. 7, 102–108. CrossRef CAS Google Scholar
Pervez, H., Yaqub, M., Manzoor, N., Tahir, M. N. & Iqbal, M. S. (2009). Acta Cryst. E65, o2858. Web of Science CrossRef IUCr Journals Google Scholar
Pervez, H., Yaqub, M., Ramzan, M., Tahir, M. N. & Iqbal, M. S. (2010c). Acta Cryst. E66, o1609. 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

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 66| Part 7| July 2010| Page o1749

doi:10.1107/S1600536810023494

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

1-[2-Oxo-5-(tri­fluoro­meth­­oxy)indolin-3-yl­­idene]-4-[4-(tri­fluoro­methyl)­phen­yl]thio­semicarbazide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[2-Oxo-5-(trifluoromethoxy)indolin-3-ylidene]-4-[4-(trifluoromethyl)phenyl]thiosemicarbazide