Literature DB >> 21587965

1-[2-Oxo-5-(trifluoro-meth-oxy)indolin-3-yl-idene]-4-[4-(trifluoro-methyl)-phen-yl]thio-semicarbazide.

Humayun Pervez, Mohammad S Iqbal, Naveeda Saira, Muhammad Yaqub, M Nawaz Tahir.   

Abstract

In the title compound, C(17)H(10)F(6)N(4)O(2)S, an intra-molecular N-H⋯N hydrogen bonds forms an S(5) ring whereas N-H⋯O and C-H⋯S inter-actions 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 mol-ecules are dimerized due to N-H⋯O inter-actions. π-π inter-actions are present between the benzene rings [centroid-centroid distance = 3.6913 (15) Å] and between the five membered ring and the trifluoro-meth-yl)phenyl ring [centroids-centroid distance = 3.7827 (16) Å]. One of the trifluoro-meth-oxy F atoms is disordered over two sites with occupancy ratio of 0.76 (3):0.24 (3). The F atoms of the p-trifluoro-methyl substituent are disordered over three sets of sites with an occupancy ratio of 0.70 (2):0.152 (11):0.147 (13).

Entities:  

Year:  2010        PMID： 21587965      PMCID： PMC3006819          DOI： 10.1107/S1600536810023494

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 448.35 Triclinic, 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[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.113 S = 1.02 3351 reflections 302 parameters 11 restraints H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.24 e Å−3 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023494/si2270sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023494/si2270Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H10F6N4O2SZ = 2
Mr = 448.35F(000) = 452
Triclinic, P1Dx = 1.589 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5452 (11) ÅCell parameters from 2191 reflections
b = 8.3177 (13) Åθ = 2.6–25.3°
c = 16.048 (2) ŵ = 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
Bruker Kappa APEXII CCD diffractometer3351 independent reflections
Radiation source: fine-focus sealed tube2191 reflections with I > 2σ(I)
graphiteRint = 0.045
Detector resolution: 8.2 pixels mm-1θmax = 25.3°, θmin = 2.6°
ω scansh = −9→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −9→9
Tmin = 0.942, Tmax = 0.952l = −19→19
13964 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0501P)2 + 0.1774P] where P = (Fo2 + 2Fc2)/3
3351 reflections(Δ/σ)max = 0.001
302 parametersΔρmax = 0.24 e Å−3
11 restraintsΔρmin = −0.24 e Å−3
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.
xyzUiso*/UeqOcc. (<1)
S10.59532 (11)0.73584 (9)0.47879 (5)0.0642 (3)
F1A0.786 (2)1.3866 (16)−0.0060 (4)0.113 (2)0.76 (3)
F20.5218 (3)1.2388 (3)−0.08045 (11)0.1050 (9)
F30.6805 (3)1.1403 (3)−0.00024 (13)0.1212 (11)
F4A0.1431 (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)
O10.8661 (2)1.2725 (2)0.48040 (11)0.0593 (7)
O20.5300 (3)1.3270 (2)0.05819 (12)0.0636 (7)
N10.8671 (3)1.4593 (3)0.39550 (13)0.0496 (7)
N20.5938 (3)1.0294 (2)0.32681 (12)0.0455 (7)
N30.6239 (3)0.9659 (3)0.39467 (13)0.0512 (7)
N40.4128 (3)0.7152 (2)0.32184 (13)0.0496 (7)
C10.8144 (3)1.3071 (3)0.41361 (16)0.0466 (9)
C20.7898 (3)1.4494 (3)0.31108 (16)0.0446 (8)
C30.8150 (3)1.5752 (3)0.26892 (17)0.0536 (9)
C40.7282 (3)1.5321 (3)0.18411 (18)0.0565 (10)
C50.6218 (3)1.3664 (3)0.14478 (16)0.0502 (9)
C60.5918 (3)1.2393 (3)0.18672 (15)0.0469 (8)
C70.6774 (3)1.2829 (3)0.27192 (15)0.0414 (8)
C80.6832 (3)1.1869 (3)0.33561 (15)0.0423 (8)
C90.6260 (5)1.2776 (5)−0.0049 (2)0.0792 (14)
C100.5363 (3)0.8008 (3)0.39415 (15)0.0454 (8)
C110.3131 (3)0.5405 (3)0.29085 (16)0.0446 (8)
C120.2921 (4)0.4258 (3)0.34125 (17)0.0564 (9)
C130.1977 (4)0.2559 (3)0.30334 (18)0.0588 (10)
C140.1225 (3)0.1981 (3)0.21696 (18)0.0523 (9)
C150.1373 (3)0.3133 (3)0.16787 (18)0.0579 (9)
C160.2315 (3)0.4828 (3)0.20459 (17)0.0543 (9)
C170.0301 (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)
F6C0.055 (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)
F1B0.727 (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)
F5B0.143 (3)−0.071 (2)0.138 (2)0.084 (4)0.152 (11)
F5C0.096 (3)−0.087 (2)0.2206 (18)0.084 (4)0.147 (13)
H3A0.700521.030890.439800.0615*
H150.083400.276340.109760.0695*
H160.240600.559880.171000.0652*
H40.741551.614600.153570.0679*
H4A0.391150.777940.289000.0595*
H60.517451.129140.159110.0563*
H120.341200.463230.400010.0676*
H130.184650.178790.337020.0704*
H10.939111.550960.431120.0594*
H30.888051.685940.296400.0643*
U11U22U33U12U13U23
S10.0831 (5)0.0563 (5)0.0494 (4)0.0101 (4)−0.0045 (4)0.0202 (3)
F1A0.091 (5)0.147 (5)0.0733 (15)−0.016 (4)0.027 (2)0.021 (2)
F20.1342 (17)0.1161 (16)0.0486 (11)0.0132 (13)−0.0175 (11)0.0230 (11)
F30.178 (2)0.136 (2)0.0743 (14)0.0873 (18)0.0274 (13)0.0277 (13)
F4A0.105 (3)0.0511 (18)0.113 (5)0.0310 (18)0.026 (3)0.004 (2)
F5A0.134 (8)0.064 (2)0.089 (3)−0.012 (3)−0.033 (4)−0.002 (2)
F6A0.086 (4)0.0480 (19)0.175 (6)−0.009 (2)0.059 (4)0.023 (3)
O10.0684 (12)0.0488 (11)0.0473 (11)−0.0009 (9)−0.0120 (9)0.0116 (9)
O20.0700 (12)0.0651 (13)0.0498 (12)0.0093 (10)−0.0072 (10)0.0186 (10)
N10.0535 (12)0.0370 (12)0.0440 (13)−0.0028 (10)−0.0063 (10)0.0041 (10)
N20.0528 (12)0.0378 (12)0.0411 (12)0.0051 (10)0.0037 (9)0.0097 (10)
N30.0637 (13)0.0373 (12)0.0429 (12)0.0005 (10)−0.0051 (10)0.0099 (10)
N40.0601 (13)0.0369 (12)0.0454 (13)0.0016 (10)−0.0052 (10)0.0149 (10)
C10.0455 (14)0.0414 (15)0.0454 (16)0.0046 (12)−0.0004 (12)0.0074 (12)
C20.0440 (13)0.0374 (14)0.0451 (15)0.0033 (11)0.0033 (11)0.0063 (12)
C30.0578 (16)0.0373 (14)0.0562 (18)0.0004 (12)0.0018 (13)0.0098 (13)
C40.0645 (17)0.0438 (16)0.0597 (18)0.0063 (13)0.0051 (14)0.0204 (14)
C50.0522 (15)0.0489 (16)0.0448 (16)0.0082 (13)−0.0023 (12)0.0125 (13)
C60.0493 (14)0.0387 (14)0.0456 (15)0.0047 (11)0.0006 (12)0.0077 (12)
C70.0415 (13)0.0363 (13)0.0399 (14)0.0037 (11)0.0015 (10)0.0067 (11)
C80.0432 (13)0.0363 (14)0.0402 (14)0.0036 (11)0.0006 (10)0.0061 (11)
C90.102 (3)0.077 (2)0.051 (2)0.007 (2)−0.0007 (19)0.0236 (18)
C100.0521 (14)0.0402 (14)0.0410 (15)0.0097 (12)0.0049 (12)0.0092 (12)
C110.0472 (14)0.0373 (14)0.0460 (15)0.0052 (11)0.0046 (11)0.0120 (12)
C120.0705 (17)0.0460 (16)0.0491 (16)0.0049 (14)0.0042 (13)0.0185 (13)
C130.0663 (17)0.0435 (16)0.066 (2)0.0047 (14)0.0098 (15)0.0235 (14)
C140.0462 (14)0.0398 (15)0.0637 (18)0.0012 (12)0.0083 (13)0.0111 (14)
C150.0589 (16)0.0521 (17)0.0497 (16)−0.0004 (13)−0.0030 (13)0.0086 (14)
C160.0620 (16)0.0464 (16)0.0490 (16)0.0010 (13)−0.0004 (13)0.0186 (13)
C170.069 (2)0.0494 (18)0.081 (3)0.0013 (17)0.0123 (19)0.0147 (17)
F6B0.080 (6)0.053 (4)0.097 (8)0.003 (3)0.026 (5)−0.007 (4)
F6C0.080 (6)0.053 (4)0.097 (8)0.003 (3)0.026 (5)−0.007 (4)
F4C0.080 (6)0.053 (4)0.097 (8)0.003 (3)0.026 (5)−0.007 (4)
F1B0.091 (5)0.147 (5)0.0733 (15)−0.016 (4)0.027 (2)0.021 (2)
F4B0.080 (6)0.053 (4)0.097 (8)0.003 (3)0.026 (5)−0.007 (4)
F5B0.080 (6)0.053 (4)0.097 (8)0.003 (3)0.026 (5)−0.007 (4)
F5C0.080 (6)0.053 (4)0.097 (8)0.003 (3)0.026 (5)−0.007 (4)
S1—C101.648 (3)N3—H3A0.8600
F1A—C91.333 (15)N4—H4A0.8600
F1B—C91.32 (3)C1—C81.500 (3)
F2—C91.311 (4)C2—C71.399 (4)
F3—C91.318 (5)C2—C31.367 (4)
F4A—C171.334 (6)C3—C41.381 (4)
F4B—C171.346 (18)C4—C51.380 (4)
F4C—C171.332 (17)C5—C61.375 (4)
F5A—C171.336 (7)C6—C71.384 (3)
F5B—C171.32 (2)C7—C81.449 (3)
F5C—C171.35 (2)C11—C161.383 (4)
F6A—C171.342 (8)C11—C121.387 (4)
F6B—C171.33 (2)C12—C131.378 (4)
F6C—C171.30 (2)C13—C141.372 (4)
O1—C11.233 (3)C14—C151.376 (4)
O2—C91.331 (4)C14—C171.489 (4)
O2—C51.423 (3)C15—C161.373 (4)
N1—C11.346 (4)C3—H30.9300
N1—C21.405 (3)C4—H40.9300
N2—N31.349 (3)C6—H60.9300
N2—C81.291 (3)C12—H120.9300
N3—C101.374 (4)C13—H130.9300
N4—C101.348 (3)C15—H150.9300
N4—C111.410 (3)C16—H160.9300
N1—H10.8600
S1···N1i3.524 (3)N3···O12.716 (3)
S1···C123.210 (3)N4···N22.627 (3)
S1···C13ii3.687 (3)N2···H4A2.1900
S1···C1iii3.652 (3)C1···C13vi3.568 (4)
S1···C12ii3.597 (3)C1···S1iii3.652 (3)
S1···H122.5600C3···F6Axii3.362 (5)
S1···H12ii2.9300C3···F4Bxii3.147 (18)
S1···H13ii3.1000C3···C16vi3.579 (3)
F1A···C43.097 (8)C3···C10xi3.558 (3)
F1A···F5Biv3.12 (3)C4···F6Axii3.309 (5)
F1B···C42.89 (2)C4···F4Bxii3.316 (19)
F2···F4Cv3.01 (2)C4···F1A3.097 (8)
F2···F6Bv3.071 (17)C4···F1B2.89 (2)
F3···C63.080 (3)C5···C16xi3.446 (3)
F3···F6Bvi3.06 (2)C6···F6Bvi3.270 (17)
F3···F5Biv2.68 (3)C6···C14xi3.562 (3)
F3···F6Civ2.78 (3)C6···F4Cvi3.23 (2)
F4B···C3vii3.147 (18)C6···F33.080 (3)
F4B···C4vii3.316 (19)C7···F4Cvi3.22 (2)
F4C···C8viii3.21 (3)C7···C12xi3.550 (4)
F4C···C6viii3.23 (2)C8···F6Avi3.151 (8)
F4C···C7viii3.22 (2)C8···F4Cvi3.21 (3)
F4C···N2viii3.19 (2)C9···F5Biv3.28 (3)
F4C···F2v3.01 (2)C10···C3i3.558 (3)
F5B···F1Aiv3.12 (3)C12···C7i3.550 (4)
F5B···F3iv2.68 (3)C12···S13.210 (3)
F5B···C9iv3.28 (3)C12···S1ii3.597 (3)
F6A···C3vii3.362 (5)C12···N1viii3.447 (4)
F6A···C8viii3.151 (8)C13···S1ii3.687 (3)
F6A···N2viii3.045 (8)C13···C1viii3.568 (4)
F6A···C4vii3.309 (5)C14···C6i3.562 (3)
F6B···F2v3.071 (17)C16···C5i3.446 (3)
F6B···C6viii3.270 (17)C16···C3viii3.579 (3)
F6B···F3viii3.06 (2)C1···H1x2.7900
F6C···F3iv2.78 (3)C1···H3A2.4100
F1A···H16ix2.7900C10···H122.8800
F1B···H42.5600H1···O1x1.9800
F1B···H16ix2.7600H1···C1x2.7900
F4A···H132.8500H3···F4Bxii2.4600
F4B···H3vii2.4600H3···F6Axii2.7900
F4B···H4vii2.8000H3···F5Cxii2.7500
F4B···H132.3300H3A···C12.4100
F4C···H4vii2.8500H3A···O12.0100
F5A···H152.4400H4···F1B2.5600
F5B···H6i2.8700H4···F6Axii2.6700
F5C···H132.4200H4···F4Bxii2.8000
F5C···H3vii2.7500H4···F4Cxii2.8500
F6A···H3vii2.7900H4A···N22.1900
F6A···H132.7500H4A···H162.2600
F6A···H4vii2.6700H6···F5Bxi2.8700
F6B···H152.5900H12···C102.8800
F6C···H152.5500H12···S12.5600
O1···N23.017 (3)H12···S1ii2.9300
O1···N1x2.829 (3)H13···F6A2.7500
O1···N32.716 (3)H13···F4A2.8500
O1···H3A2.0100H13···S1ii3.1000
O1···H1x1.9800H13···F4B2.3300
N1···O1x2.829 (3)H13···F5C2.4200
N1···C12vi3.447 (4)H15···F6C2.5500
N1···S1xi3.524 (3)H15···F6B2.5900
N2···O13.017 (3)H15···F5A2.4400
N2···N42.627 (3)H16···F1Aix2.7900
N2···F4Cvi3.19 (2)H16···F1Bix2.7600
N2···F6Avi3.045 (8)H16···H4A2.2600
C5—O2—C9115.9 (2)N4—C11—C16116.8 (2)
C1—N1—C2111.5 (2)N4—C11—C12124.2 (2)
N3—N2—C8116.3 (2)C11—C12—C13119.3 (2)
N2—N3—C10122.3 (2)C12—C13—C14121.4 (2)
C10—N4—C11131.0 (2)C13—C14—C15119.2 (2)
C2—N1—H1124.00C13—C14—C17119.8 (2)
C1—N1—H1124.00C15—C14—C17121.0 (3)
N2—N3—H3A119.00C14—C15—C16120.1 (3)
C10—N3—H3A119.00C11—C16—C15120.9 (2)
C10—N4—H4A114.00F4A—C17—C14113.1 (4)
C11—N4—H4A114.00F4A—C17—F5A105.1 (6)
O1—C1—N1126.9 (2)F4A—C17—F6A104.2 (4)
N1—C1—C8106.3 (2)F5C—C17—C14111.4 (10)
O1—C1—C8126.8 (2)F6B—C17—C14108.0 (8)
N1—C2—C7109.2 (2)F6C—C17—C14112.3 (9)
N1—C2—C3128.5 (2)F4B—C17—F5B107.0 (15)
C3—C2—C7122.3 (2)F4B—C17—F6B103.6 (16)
C2—C3—C4117.7 (2)F4C—C17—F5C106.9 (15)
C3—C4—C5119.9 (2)F4C—C17—F6C107.7 (18)
C4—C5—C6123.2 (2)F5B—C17—F6B116.9 (16)
O2—C5—C4118.6 (2)F5C—C17—F6C106.5 (15)
O2—C5—C6118.1 (2)F5A—C17—F6A106.0 (6)
C5—C6—C7116.9 (2)F5A—C17—C14115.0 (3)
C2—C7—C8106.7 (2)F6A—C17—C14112.5 (4)
C6—C7—C8133.3 (2)F4B—C17—C14109.2 (8)
C2—C7—C6120.0 (2)F4C—C17—C14111.7 (12)
C1—C8—C7106.2 (2)F5B—C17—C14111.7 (9)
N2—C8—C1127.0 (2)C2—C3—H3121.00
N2—C8—C7126.9 (2)C4—C3—H3121.00
F1A—C9—F3100.9 (7)C3—C4—H4120.00
F1A—C9—F2109.0 (4)C5—C4—H4120.00
F1B—C9—O297.3 (12)C5—C6—H6122.00
F1A—C9—O2117.2 (5)C7—C6—H6122.00
F2—C9—F3107.5 (3)C11—C12—H12120.00
F2—C9—O2109.1 (3)C13—C12—H12120.00
F1B—C9—F2100.0 (11)C12—C13—H13119.00
F3—C9—O2112.6 (3)C14—C13—H13119.00
F1B—C9—F3128.7 (14)C14—C15—H15120.00
S1—C10—N3117.20 (18)C16—C15—H15120.00
S1—C10—N4129.66 (19)C11—C16—H16120.00
N3—C10—N4113.1 (2)C15—C16—H16120.00
C12—C11—C16119.0 (2)
C9—O2—C5—C488.2 (3)C2—C3—C4—C5−0.5 (4)
C9—O2—C5—C6−95.3 (3)C3—C4—C5—O2178.3 (2)
C5—O2—C9—F1A−58.3 (7)C3—C4—C5—C61.9 (4)
C5—O2—C9—F2177.3 (2)O2—C5—C6—C7−177.7 (2)
C5—O2—C9—F358.1 (4)C4—C5—C6—C7−1.3 (4)
C2—N1—C1—O1176.1 (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—N2177.6 (2)
C1—N1—C2—C71.2 (3)C2—C7—C8—C1−2.6 (3)
C8—N2—N3—C10179.4 (2)C6—C7—C8—N2−4.4 (4)
N3—N2—C8—C1−1.0 (4)C6—C7—C8—C1175.4 (3)
N3—N2—C8—C7178.8 (2)N4—C11—C12—C13−177.5 (3)
N2—N3—C10—S1176.33 (19)C16—C11—C12—C132.9 (4)
N2—N3—C10—N4−3.3 (3)N4—C11—C16—C15177.6 (2)
C11—N4—C10—S1−8.8 (4)C12—C11—C16—C15−2.7 (4)
C11—N4—C10—N3170.8 (2)C11—C12—C13—C14−0.6 (4)
C10—N4—C11—C1215.8 (4)C12—C13—C14—C15−1.9 (4)
C10—N4—C11—C16−164.5 (2)C12—C13—C14—C17176.8 (3)
O1—C1—C8—N24.2 (4)C13—C14—C15—C162.1 (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—C73.3 (3)C13—C14—C17—F5A178.1 (6)
N1—C2—C3—C4177.7 (2)C13—C14—C17—F6A56.5 (5)
C7—C2—C3—C4−1.5 (4)C15—C14—C17—F4A117.4 (5)
N1—C2—C7—C6−177.3 (2)C15—C14—C17—F5A−3.3 (6)
N1—C2—C7—C81.0 (3)C15—C14—C17—F6A−124.9 (4)
C3—C2—C7—C62.1 (4)C14—C15—C16—C110.2 (4)
C3—C2—C7—C8−179.7 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1···O1x0.86001.98002.829 (3)168.00
N3—H3A···O10.86002.01002.716 (3)138.00
N4—H4A···N20.86002.19002.627 (3)111.00
C12—H12···S10.93002.56003.210 (3)128.00
C15—H15···F5A0.93002.44002.763 (6)100.00
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O1i0.861.982.829 (3)168
N3—H3A⋯O10.862.012.716 (3)138
N4—H4A⋯N20.862.192.627 (3)111
C12—H12⋯S10.932.563.210 (3)128

Symmetry code: (i) .

  5 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Authors:  Humayun Pervez; Muhammad Yaqub; Nazia Manzoor; M Nawaz Tahir; M Saeed Iqbal
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-28

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Authors:  Humayun Pervez; Mohammad S Iqbal; Naveeda Saira; Muhammad Yaqub; M Nawaz Tahir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-24

4.  4-(2-Ethyl-phen-yl)-1-(2-oxoindolin-3-yl-idene)thio-semicarbazide.

Authors:  Humayun Pervez; Muhammad Yaqub; Muhammad Ramzan; M Nawaz Tahir; Mohammad S Iqbal
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-09

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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1.  Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones.

Authors:  Humayun Pervez; Naveeda Saira; Mohammad Saeed Iqbal; Muhammad Yaqub; Khalid Mohammed Khan
Journal:  Molecules       Date:  2011-07-29       Impact factor: 4.411
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