Literature DB >> 21579211

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

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

Abstract

The asymmetric unit of the title compound, C(17)H(12)ClF(3)N(4)O(2)S, contains two mol-ecules, which differ in their planarity and hydrogen bonding. In one mol-ecule, the 2-oxoindolin (C(8)/N/O A), thio-semicarbazide (N(3)/C/S B) and 5-chloro-2-methyl-phenyl (C(7)/Cl C) units are planar with r.m.s. deviations of 0.0110, 0.0173 and 0.0259 Å, respectively. The dihedral angles A/B, B/C and A/C are 1.74 (15), 40.70 (13) and 41.00 (11)°, respectively. In the other mol-ecule the deviations are 0.0455, 0.0007 and 0.0143 Å, respectively, and the dihedral angles are 5.01 (14), 4.53 (16) and 3.38 (13)°, respectively. In both mol-ecules, intra-molecular N-H⋯N and N-H⋯O hydrogen bonds form S(5) and S(6) ring motifs, respectively and C-H⋯S interactions occur. In one of the molecules, an intramolecular C-H⋯F interaction is also present. In the crystal, the mol-ecules are linked by N-H⋯O, C-H⋯F, C-H⋯O and N-H⋯S hydrogen bonding, forming a polymeric network.

Entities:  

Year:  2010        PMID： 21579211      PMCID： PMC2979057          DOI： 10.1107/S1600536810014650

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


Related literature

For our work on 1H-indole-2,3-dione derivatives having pharmaceutical applications, see: Pervez et al. (2007 ▶, 2008 ▶, 2009a ▶, 2010a ▶). For the structures of 1-(5-nitro-2-oxoindolin-3-yl­idene)-4-o-tolyl­thio­semicarbazide and 4-(2-fluoro­phen­yl)-1-(2-oxoindolin-3-yl­idene)thio­semicarbazide, see: Pervez et al. (2009b ▶, 2010b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H12ClF3N4O2S M = 428.82 Triclinic, a = 10.5808 (5) Å b = 11.0262 (5) Å c = 17.1743 (7) Å α = 102.855 (3)° β = 94.766 (3)° γ = 107.814 (2)° V = 1834.96 (15) Å3 Z = 4 Mo Kα radiation μ = 0.37 mm−1 T = 296 K 0.24 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.924, T max = 0.945 33611 measured reflections 6822 independent reflections 3927 reflections with I > 2σ(I) R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.145 S = 1.02 6822 reflections 507 parameters H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.36 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/S1600536810014650/bq2207sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014650/bq2207Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H12ClF3N4O2SZ = 4
Mr = 428.82F(000) = 872
Triclinic, P1Dx = 1.552 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5808 (5) ÅCell parameters from 6822 reflections
b = 11.0262 (5) Åθ = 2.1–25.5°
c = 17.1743 (7) ŵ = 0.37 mm−1
α = 102.855 (3)°T = 296 K
β = 94.766 (3)°Prism, red
γ = 107.814 (2)°0.24 × 0.18 × 0.16 mm
V = 1834.96 (15) Å3
Bruker Kappa APEXII CCD diffractometer6822 independent reflections
Radiation source: fine-focus sealed tube3927 reflections with I > 2σ(I)
graphiteRint = 0.049
Detector resolution: 7.80 pixels mm-1θmax = 25.5°, θmin = 2.1°
ω scansh = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −13→13
Tmin = 0.924, Tmax = 0.945l = −20→20
33611 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0588P)2 + 0.8346P] where P = (Fo2 + 2Fc2)/3
6822 reflections(Δ/σ)max < 0.001
507 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.36 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 esds 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*/Ueq
Cl10.90141 (12)1.08034 (18)0.04378 (8)0.1311 (7)
S10.73013 (8)1.08876 (10)0.33045 (6)0.0663 (4)
F1−0.2587 (4)0.5431 (3)0.0906 (2)0.1816 (18)
F2−0.2738 (3)0.6739 (3)0.02089 (18)0.1430 (16)
F3−0.0876 (4)0.6495 (4)0.05415 (19)0.167 (2)
O10.3721 (2)0.8851 (2)0.46034 (14)0.0616 (9)
O2−0.1786 (3)0.7545 (3)0.14412 (19)0.0825 (11)
N10.1403 (2)0.7922 (2)0.42522 (16)0.0498 (9)
N20.3438 (3)0.9308 (2)0.29315 (17)0.0503 (9)
N30.4732 (2)0.9813 (2)0.32968 (17)0.0522 (9)
N40.5207 (3)1.0337 (3)0.21286 (17)0.0585 (10)
C10.2674 (3)0.8546 (3)0.4138 (2)0.0494 (11)
C20.2519 (3)0.8751 (3)0.3308 (2)0.0472 (11)
C30.1102 (3)0.8184 (3)0.29786 (19)0.0455 (11)
C40.0382 (3)0.8115 (3)0.2255 (2)0.0552 (12)
C5−0.1000 (3)0.7532 (3)0.2146 (2)0.0606 (14)
C6−0.1641 (3)0.7044 (3)0.2728 (2)0.0646 (14)
C7−0.0922 (3)0.7113 (3)0.3450 (2)0.0587 (14)
C80.0459 (3)0.7697 (3)0.35726 (19)0.0457 (11)
C90.5704 (3)1.0342 (3)0.2870 (2)0.0504 (11)
C100.5856 (3)1.0824 (3)0.1519 (2)0.0552 (12)
C110.5210 (4)1.1454 (3)0.1090 (2)0.0644 (14)
C120.5790 (5)1.1884 (4)0.0471 (3)0.0876 (19)
C130.6963 (5)1.1717 (5)0.0280 (3)0.0936 (19)
C140.7571 (4)1.1069 (4)0.0704 (2)0.0796 (16)
C150.7029 (3)1.0613 (4)0.1325 (2)0.0666 (14)
C160.3887 (4)1.1624 (4)0.1257 (2)0.0859 (17)
C17−0.1989 (6)0.6580 (7)0.0794 (4)0.107 (3)
Cl20.91864 (10)0.86095 (10)0.77449 (6)0.0815 (4)
S20.40866 (10)0.58900 (11)0.67685 (6)0.0801 (4)
F40.4264 (4)0.5047 (4)0.1554 (2)0.1422 (17)
F50.4754 (3)0.7019 (3)0.2115 (2)0.1348 (14)
F60.4451 (3)0.6393 (4)0.08329 (19)0.1460 (16)
O30.0157 (2)0.3691 (2)0.47803 (14)0.0558 (8)
O40.2739 (4)0.5967 (4)0.1420 (2)0.1177 (16)
N5−0.0455 (3)0.3792 (3)0.34712 (17)0.0574 (10)
N60.2839 (2)0.5485 (2)0.45305 (15)0.0460 (9)
N70.2893 (2)0.5392 (2)0.52977 (15)0.0482 (9)
N80.5052 (2)0.6698 (3)0.54981 (16)0.0540 (9)
C180.0396 (3)0.4055 (3)0.4167 (2)0.0470 (11)
C190.1729 (3)0.4892 (3)0.40341 (18)0.0431 (10)
C200.1555 (3)0.4956 (3)0.32001 (19)0.0477 (11)
C210.2453 (3)0.5523 (3)0.2743 (2)0.0610 (12)
C220.1959 (4)0.5391 (4)0.1956 (2)0.0720 (16)
C230.0625 (5)0.4747 (4)0.1631 (2)0.0767 (16)
C24−0.0288 (4)0.4190 (4)0.2091 (2)0.0694 (12)
C250.0206 (3)0.4288 (3)0.2880 (2)0.0530 (11)
C260.4070 (3)0.6034 (3)0.58372 (18)0.0458 (10)
C270.6420 (3)0.7470 (3)0.5784 (2)0.0466 (10)
C280.7111 (3)0.8068 (3)0.5231 (2)0.0475 (11)
C290.8460 (3)0.8802 (3)0.5489 (3)0.0613 (14)
C300.9113 (3)0.8970 (3)0.6241 (3)0.0653 (14)
C310.8411 (3)0.8388 (3)0.6771 (2)0.0588 (14)
C320.7060 (3)0.7626 (3)0.6551 (2)0.0545 (11)
C330.6436 (3)0.7917 (3)0.4397 (2)0.0634 (14)
C340.3975 (7)0.6097 (6)0.1467 (3)0.104 (2)
H10.120710.769580.468710.0597*
H30.494610.980450.378920.0626*
H40.080740.844530.185660.0664*
H4A0.434790.997790.200020.0702*
H6−0.257340.666260.263410.0777*
H7−0.135350.677700.384420.0699*
H120.537051.230230.017300.1050*
H130.734711.20383−0.013260.1123*
H150.744091.017130.160950.0798*
H16A0.363211.211420.091220.1291*
H16B0.398121.209210.181290.1291*
H16C0.320681.077220.115240.1291*
H5−0.130380.336750.340110.0688*
H7A0.219240.492980.545110.0579*
H80.479950.664510.499910.0648*
H210.335510.597470.295810.0737*
H230.033140.468490.109310.0919*
H24−0.119480.376830.187700.0829*
H290.894180.919940.513080.0734*
H301.002080.947080.639310.0786*
H320.659490.722790.691430.0653*
H33A0.704360.847490.413520.0949*
H33B0.618780.701480.408920.0949*
H33C0.564480.816640.443080.0949*
U11U22U33U12U13U23
Cl10.0695 (8)0.2284 (17)0.0752 (8)0.0309 (9)0.0249 (6)0.0215 (9)
S10.0366 (5)0.0842 (7)0.0749 (7)0.0045 (4)0.0044 (4)0.0380 (5)
F10.236 (4)0.099 (2)0.140 (3)−0.011 (3)−0.058 (3)0.019 (2)
F20.142 (3)0.175 (3)0.095 (2)0.045 (2)−0.042 (2)0.035 (2)
F30.154 (3)0.267 (5)0.086 (2)0.105 (3)0.011 (2)0.010 (2)
O10.0414 (13)0.0727 (16)0.0665 (16)0.0138 (12)0.0039 (12)0.0189 (12)
O20.0667 (18)0.093 (2)0.082 (2)0.0219 (15)−0.0078 (16)0.0253 (17)
N10.0394 (15)0.0537 (16)0.0560 (18)0.0107 (12)0.0131 (13)0.0189 (13)
N20.0359 (15)0.0474 (15)0.0676 (18)0.0107 (12)0.0108 (13)0.0187 (14)
N30.0374 (15)0.0556 (16)0.0633 (18)0.0077 (12)0.0101 (13)0.0254 (14)
N40.0346 (14)0.0734 (19)0.0626 (19)0.0031 (13)0.0038 (14)0.0303 (15)
C10.044 (2)0.0438 (18)0.061 (2)0.0150 (15)0.0143 (17)0.0126 (16)
C20.0379 (18)0.0396 (17)0.064 (2)0.0102 (14)0.0147 (16)0.0149 (15)
C30.0398 (18)0.0387 (17)0.056 (2)0.0107 (14)0.0100 (16)0.0113 (15)
C40.052 (2)0.051 (2)0.064 (2)0.0149 (16)0.0162 (18)0.0184 (17)
C50.045 (2)0.062 (2)0.071 (3)0.0138 (17)−0.0010 (18)0.0194 (19)
C60.0373 (19)0.069 (2)0.084 (3)0.0099 (17)0.0101 (19)0.024 (2)
C70.0380 (19)0.064 (2)0.074 (3)0.0087 (16)0.0152 (18)0.0275 (19)
C80.0402 (18)0.0387 (17)0.058 (2)0.0120 (14)0.0141 (16)0.0119 (15)
C90.0404 (18)0.0454 (18)0.065 (2)0.0081 (15)0.0110 (16)0.0216 (16)
C100.050 (2)0.057 (2)0.047 (2)0.0020 (16)−0.0002 (16)0.0159 (17)
C110.078 (3)0.057 (2)0.047 (2)0.0118 (19)−0.0008 (19)0.0103 (17)
C120.118 (4)0.088 (3)0.058 (3)0.030 (3)0.011 (3)0.029 (2)
C130.108 (4)0.097 (3)0.053 (3)−0.003 (3)0.015 (3)0.026 (2)
C140.058 (2)0.099 (3)0.056 (3)−0.002 (2)0.009 (2)0.009 (2)
C150.050 (2)0.084 (3)0.058 (2)0.0109 (19)0.0067 (18)0.020 (2)
C160.098 (3)0.104 (3)0.066 (3)0.055 (3)−0.001 (2)0.018 (2)
C170.087 (4)0.135 (5)0.085 (4)0.023 (4)−0.011 (3)0.033 (4)
Cl20.0671 (6)0.0745 (7)0.0856 (7)0.0259 (5)−0.0283 (5)−0.0016 (5)
S20.0708 (7)0.0896 (7)0.0513 (6)−0.0154 (5)−0.0063 (5)0.0270 (5)
F40.186 (3)0.154 (3)0.144 (3)0.096 (3)0.083 (2)0.077 (2)
F50.138 (3)0.127 (2)0.110 (2)0.001 (2)0.033 (2)0.029 (2)
F60.164 (3)0.208 (3)0.106 (2)0.065 (3)0.065 (2)0.101 (2)
O30.0511 (13)0.0498 (13)0.0574 (15)0.0047 (10)0.0092 (11)0.0128 (11)
O40.094 (2)0.195 (4)0.086 (2)0.048 (3)0.019 (2)0.079 (2)
N50.0376 (15)0.0573 (17)0.0593 (19)0.0010 (13)−0.0052 (14)0.0053 (14)
N60.0423 (15)0.0445 (15)0.0426 (16)0.0062 (12)0.0007 (12)0.0082 (12)
N70.0407 (15)0.0456 (15)0.0450 (16)−0.0020 (12)0.0001 (12)0.0108 (12)
N80.0378 (15)0.0667 (18)0.0464 (16)0.0001 (13)−0.0026 (12)0.0205 (14)
C180.0428 (19)0.0360 (17)0.054 (2)0.0095 (14)0.0022 (16)0.0027 (15)
C190.0413 (18)0.0376 (16)0.0441 (19)0.0080 (14)0.0017 (14)0.0072 (14)
C200.0481 (19)0.0413 (18)0.048 (2)0.0113 (15)0.0013 (16)0.0076 (14)
C210.055 (2)0.071 (2)0.053 (2)0.0143 (18)−0.0011 (18)0.0215 (18)
C220.077 (3)0.090 (3)0.056 (2)0.030 (2)0.011 (2)0.030 (2)
C230.093 (3)0.091 (3)0.047 (2)0.036 (3)−0.007 (2)0.019 (2)
C240.066 (2)0.069 (2)0.058 (2)0.019 (2)−0.015 (2)0.0007 (19)
C250.051 (2)0.0454 (19)0.050 (2)0.0111 (16)−0.0055 (17)−0.0003 (16)
C260.0430 (18)0.0397 (17)0.0457 (19)0.0050 (14)−0.0019 (15)0.0088 (14)
C270.0359 (17)0.0374 (17)0.061 (2)0.0091 (14)−0.0010 (16)0.0095 (15)
C280.0397 (18)0.0409 (17)0.063 (2)0.0167 (14)0.0095 (16)0.0111 (15)
C290.041 (2)0.049 (2)0.092 (3)0.0141 (16)0.015 (2)0.0147 (19)
C300.0362 (19)0.051 (2)0.097 (3)0.0117 (16)0.003 (2)0.003 (2)
C310.046 (2)0.0453 (19)0.075 (3)0.0206 (17)−0.0128 (18)−0.0033 (17)
C320.047 (2)0.0478 (19)0.060 (2)0.0107 (16)−0.0034 (17)0.0084 (16)
C330.052 (2)0.072 (2)0.075 (3)0.0215 (18)0.0204 (19)0.032 (2)
C340.146 (5)0.105 (4)0.064 (3)0.029 (4)0.026 (4)0.044 (3)
Cl1—C141.719 (5)C6—C71.374 (5)
Cl2—C311.732 (3)C7—C81.381 (5)
S1—C91.656 (3)C10—C151.384 (5)
S2—C261.641 (3)C10—C111.388 (5)
F1—C171.296 (8)C11—C121.373 (6)
F2—C171.304 (7)C11—C161.510 (6)
F3—C171.311 (8)C12—C131.365 (8)
F4—C341.320 (8)C13—C141.375 (7)
F5—C341.335 (7)C14—C151.372 (5)
F6—C341.302 (7)C4—H40.9300
O1—C11.218 (4)C6—H60.9300
O2—C51.416 (5)C7—H70.9300
O2—C171.307 (8)C12—H120.9300
O3—C181.227 (4)C13—H130.9300
O4—C221.413 (6)C15—H150.9300
O4—C341.265 (9)C16—H16A0.9600
N1—C81.396 (4)C16—H16C0.9600
N1—C11.363 (4)C16—H16B0.9600
N2—N31.347 (4)C18—C191.498 (5)
N2—C21.287 (4)C19—C201.449 (4)
N3—C91.373 (4)C20—C211.374 (5)
N4—C91.335 (4)C20—C251.389 (5)
N4—C101.414 (4)C21—C221.367 (5)
N1—H10.8600C22—C231.374 (7)
N3—H30.8600C23—C241.384 (6)
N4—H4A0.8600C24—C251.380 (5)
N5—C251.397 (5)C27—C281.404 (5)
N5—C181.353 (4)C27—C321.380 (5)
N6—C191.284 (4)C28—C331.497 (5)
N6—N71.342 (3)C28—C291.385 (5)
N7—C261.374 (4)C29—C301.359 (7)
N8—C271.415 (4)C30—C311.369 (5)
N8—C261.334 (4)C31—C321.388 (5)
N5—H50.8600C21—H210.9300
N7—H7A0.8600C23—H230.9300
N8—H80.8600C24—H240.9300
C1—C21.496 (5)C29—H290.9300
C2—C31.445 (5)C30—H300.9300
C3—C81.388 (5)C32—H320.9300
C3—C41.377 (5)C33—H33A0.9600
C4—C51.383 (5)C33—H33B0.9600
C5—C61.370 (5)C33—H33C0.9600
Cl1···Cl1i3.369 (2)C21···F42.984 (5)
Cl1···Cl2ii3.3384 (17)C21···C33.599 (5)
Cl2···C25iii3.409 (3)C21···C23.452 (5)
Cl2···C4iv3.499 (3)C21···F52.930 (5)
Cl2···Cl1ii3.3384 (17)C21···C13.575 (5)
S1···N5v3.287 (3)C22···C33.600 (5)
S1···C153.325 (3)C25···Cl2iii3.409 (3)
S2···C323.245 (4)C25···C83.600 (5)
S1···H152.8700C28···C1iv3.578 (5)
S1···H30ii3.0000C29···C2iv3.494 (5)
S1···H5v2.6400C29···C1iv3.441 (5)
S2···H33Biii3.1300C30···O3iii3.406 (4)
S2···H322.5700C30···C2iv3.451 (5)
S2···H16Biv3.0100C30···C4iv3.509 (5)
F1···C63.142 (5)C30···C18iii3.459 (5)
F3···C43.030 (5)C30···C8iv3.500 (5)
F4···C212.984 (5)C30···C3iv3.211 (5)
F5···C212.930 (5)C31···C3iv3.576 (5)
F6···C12vi3.284 (6)C31···C19iii3.525 (5)
F2···H16Avii2.7800C31···C18iii3.454 (5)
F3···H42.7800C32···C19iii3.393 (5)
F4···H212.7700C32···S23.245 (4)
F5···H212.3800C33···O13.355 (4)
F6···H12vi2.4700C33···C7xi3.588 (5)
O1···C333.355 (4)C1···H32.5800
O1···N32.841 (3)C9···H152.9600
O1···N23.030 (4)C14···H24v3.0200
O1···O1iv3.043 (3)C16···H4A2.5700
O3···N63.049 (3)C18···H7A2.5800
O3···N1viii2.937 (3)C26···H322.8700
O3···N72.863 (3)C32···H16Biv3.0900
O3···O3viii2.945 (3)C33···H7xi3.1000
O3···C18viii2.976 (4)C33···H82.3400
O3···C30iii3.406 (4)C34···H212.7200
O1···H32.2100H1···O3viii2.1800
O1···H33C2.4000H3···H33C2.5700
O1···H3iv2.8400H3···C12.5800
O3···H7A2.2200H3···O12.2100
O3···H7viii2.8100H3···O1iv2.8400
O3···H1viii2.1800H4···F32.7800
N1···O3viii2.937 (3)H4A···N22.0900
N1···C203.424 (4)H4A···C162.5700
N1···C193.405 (4)H4A···H16B2.5600
N2···N42.553 (4)H4A···H16C2.3000
N2···O13.030 (4)H5···S1ix2.6400
N3···O12.841 (3)H7···C33x3.1000
N4···N22.553 (4)H7···O3viii2.8100
N5···S1ix3.287 (3)H7···H7Aviii2.4400
N6···N82.546 (3)H7A···H7viii2.4400
N6···O33.049 (3)H7A···O32.2200
N7···O32.863 (3)H7A···C182.5800
N8···N62.546 (3)H8···N62.0600
N2···H4A2.0900H8···H33C2.1300
N4···H16B2.7600H8···C332.3400
N4···H16C2.8100H8···H33B2.2500
N6···H212.9300H12···H16A2.3000
N6···H82.0600H12···F6vi2.4700
N8···H33B2.8300H15···S12.8700
N8···H33C2.7000H15···C92.9600
C1···C213.575 (5)H16A···H122.3000
C1···C29iv3.441 (5)H16A···F2vii2.7800
C1···C28iv3.578 (5)H16B···N42.7600
C2···C213.452 (5)H16B···H4A2.5600
C2···C30iv3.451 (5)H16B···S2iv3.0100
C2···C29iv3.494 (5)H16B···C32iv3.0900
C3···C223.600 (5)H16B···H32iv2.3400
C3···C213.599 (5)H16C···N42.8100
C3···C31iv3.576 (5)H16C···H4A2.3000
C3···C30iv3.211 (5)H21···F42.7700
C4···F33.030 (5)H21···F52.3800
C4···C30iv3.509 (5)H21···N62.9300
C4···Cl2iv3.499 (3)H21···C342.7200
C6···F13.142 (5)H24···C14ix3.0200
C7···C33x3.588 (5)H29···H33A2.3300
C8···C30iv3.500 (5)H29···H29ii2.5400
C8···C203.507 (5)H30···S1ii3.0000
C8···C253.600 (5)H32···S22.5700
C12···F6vi3.284 (6)H32···C262.8700
C15···S13.325 (3)H32···H16Biv2.3400
C18···C31iii3.454 (5)H33A···H292.3300
C18···C30iii3.459 (5)H33B···N82.8300
C18···O3viii2.976 (4)H33B···H82.2500
C18···C18viii3.471 (5)H33B···S2iii3.1300
C19···C31iii3.525 (5)H33C···O12.4000
C19···C32iii3.393 (5)H33C···N82.7000
C19···N13.405 (4)H33C···H32.5700
C20···C83.507 (5)H33C···H82.1300
C20···N13.424 (4)
C5—O2—C17117.6 (4)C11—C12—H12119.00
C22—O4—C34120.9 (4)C14—C13—H13120.00
C1—N1—C8111.3 (3)C12—C13—H13120.00
N3—N2—C2119.8 (3)C10—C15—H15121.00
N2—N3—C9118.9 (3)C14—C15—H15121.00
C9—N4—C10130.8 (3)C11—C16—H16A110.00
C1—N1—H1124.00H16A—C16—H16C109.00
C8—N1—H1124.00H16B—C16—H16C109.00
N2—N3—H3121.00H16A—C16—H16B110.00
C9—N3—H3121.00C11—C16—H16B109.00
C9—N4—H4A115.00C11—C16—H16C109.00
C10—N4—H4A115.00O3—C18—N5128.5 (3)
C18—N5—C25112.1 (3)O3—C18—C19126.3 (3)
N7—N6—C19119.3 (2)N5—C18—C19105.2 (3)
N6—N7—C26119.9 (2)N6—C19—C18129.8 (3)
C26—N8—C27133.7 (3)N6—C19—C20123.7 (3)
C25—N5—H5124.00C18—C19—C20106.5 (3)
C18—N5—H5124.00C19—C20—C25106.9 (3)
C26—N7—H7A120.00C19—C20—C21131.6 (3)
N6—N7—H7A120.00C21—C20—C25121.6 (3)
C27—N8—H8113.00C20—C21—C22116.9 (3)
C26—N8—H8113.00O4—C22—C21123.7 (4)
O1—C1—C2127.0 (3)C21—C22—C23122.3 (4)
N1—C1—C2105.4 (3)O4—C22—C23113.8 (3)
O1—C1—N1127.6 (3)C22—C23—C24121.0 (3)
N2—C2—C1128.5 (3)C23—C24—C25117.1 (4)
N2—C2—C3124.6 (3)N5—C25—C24129.9 (3)
C1—C2—C3106.9 (3)N5—C25—C20109.1 (3)
C2—C3—C4132.3 (3)C20—C25—C24121.0 (3)
C4—C3—C8121.1 (3)S2—C26—N8129.8 (3)
C2—C3—C8106.6 (3)S2—C26—N7118.1 (2)
C3—C4—C5117.1 (3)N7—C26—N8112.1 (3)
C4—C5—C6122.1 (3)C28—C27—C32121.1 (3)
O2—C5—C6118.8 (3)N8—C27—C28115.8 (3)
O2—C5—C4118.8 (3)N8—C27—C32123.1 (3)
C5—C6—C7120.7 (3)C27—C28—C33122.1 (3)
C6—C7—C8118.1 (3)C29—C28—C33121.0 (3)
N1—C8—C3109.9 (3)C27—C28—C29116.9 (3)
C3—C8—C7120.9 (3)C28—C29—C30123.1 (4)
N1—C8—C7129.3 (3)C29—C30—C31118.8 (3)
N3—C9—N4113.4 (3)C30—C31—C32121.3 (3)
S1—C9—N4128.0 (3)Cl2—C31—C32118.2 (3)
S1—C9—N3118.7 (2)Cl2—C31—C30120.5 (3)
N4—C10—C15121.9 (3)C27—C32—C31118.8 (3)
C11—C10—C15121.6 (3)F6—C34—O4111.7 (5)
N4—C10—C11116.4 (3)F4—C34—F5101.4 (5)
C10—C11—C12117.5 (4)F4—C34—F6107.2 (5)
C10—C11—C16122.6 (3)F4—C34—O4114.5 (6)
C12—C11—C16119.8 (4)F5—C34—F6107.1 (5)
C11—C12—C13122.1 (5)F5—C34—O4114.1 (5)
C12—C13—C14119.3 (5)C20—C21—H21122.00
Cl1—C14—C15119.8 (3)C22—C21—H21121.00
C13—C14—C15120.9 (4)C22—C23—H23119.00
Cl1—C14—C13119.3 (3)C24—C23—H23120.00
C10—C15—C14118.6 (4)C23—C24—H24121.00
F2—C17—O2109.5 (6)C25—C24—H24122.00
F3—C17—O2113.4 (6)C28—C29—H29118.00
F2—C17—F3108.2 (5)C30—C29—H29118.00
F1—C17—F3104.7 (6)C29—C30—H30121.00
F1—C17—O2112.9 (5)C31—C30—H30121.00
F1—C17—F2107.9 (5)C27—C32—H32121.00
C3—C4—H4121.00C31—C32—H32121.00
C5—C4—H4121.00C28—C33—H33A109.00
C5—C6—H6120.00C28—C33—H33B110.00
C7—C6—H6120.00C28—C33—H33C110.00
C6—C7—H7121.00H33A—C33—H33B109.00
C8—C7—H7121.00H33A—C33—H33C109.00
C13—C12—H12119.00H33B—C33—H33C109.00
C17—O2—C5—C487.7 (5)C4—C5—C6—C7−0.3 (5)
C17—O2—C5—C6−97.9 (5)O2—C5—C6—C7−174.6 (3)
C5—O2—C17—F159.2 (7)C5—C6—C7—C80.5 (5)
C5—O2—C17—F2179.4 (4)C6—C7—C8—N1178.0 (3)
C5—O2—C17—F3−59.7 (7)C6—C7—C8—C3−0.8 (5)
C22—O4—C34—F444.9 (6)C15—C10—C11—C12−1.1 (5)
C34—O4—C22—C2133.5 (7)N4—C10—C11—C160.2 (5)
C34—O4—C22—C23−150.4 (5)C11—C10—C15—C141.5 (5)
C22—O4—C34—F5−71.3 (7)C15—C10—C11—C16176.3 (3)
C22—O4—C34—F6167.1 (4)N4—C10—C15—C14177.4 (3)
C8—N1—C1—O1−177.9 (3)N4—C10—C11—C12−177.2 (3)
C8—N1—C1—C20.7 (3)C10—C11—C12—C13−0.5 (6)
C1—N1—C8—C3−0.2 (4)C16—C11—C12—C13−178.0 (4)
C1—N1—C8—C7−179.1 (3)C11—C12—C13—C141.7 (7)
N3—N2—C2—C3179.6 (3)C12—C13—C14—Cl1177.5 (4)
N3—N2—C2—C1−1.0 (5)C12—C13—C14—C15−1.3 (7)
C2—N2—N3—C9176.7 (3)Cl1—C14—C15—C10−179.1 (3)
N2—N3—C9—N42.9 (4)C13—C14—C15—C10−0.3 (6)
N2—N3—C9—S1−176.7 (2)O3—C18—C19—N6−6.6 (6)
C10—N4—C9—N3177.6 (3)O3—C18—C19—C20174.5 (3)
C9—N4—C10—C11−139.6 (4)N5—C18—C19—N6173.9 (3)
C10—N4—C9—S1−2.8 (6)N5—C18—C19—C20−5.0 (4)
C9—N4—C10—C1544.3 (6)N6—C19—C20—C215.1 (6)
C25—N5—C18—O3−175.1 (3)N6—C19—C20—C25−175.2 (3)
C25—N5—C18—C194.4 (4)C18—C19—C20—C21−176.0 (3)
C18—N5—C25—C20−2.2 (4)C18—C19—C20—C253.7 (4)
C18—N5—C25—C24177.6 (4)C19—C20—C21—C22179.2 (4)
C19—N6—N7—C26−179.3 (3)C25—C20—C21—C22−0.5 (5)
N7—N6—C19—C20178.4 (3)C19—C20—C25—N5−1.2 (4)
N7—N6—C19—C18−0.3 (5)C19—C20—C25—C24179.0 (3)
N6—N7—C26—N8−0.1 (4)C21—C20—C25—N5178.6 (3)
N6—N7—C26—S2−180.0 (2)C21—C20—C25—C24−1.2 (5)
C27—N8—C26—S21.5 (6)C20—C21—C22—O4177.0 (4)
C27—N8—C26—N7−178.3 (3)C20—C21—C22—C231.2 (6)
C26—N8—C27—C28−176.9 (3)O4—C22—C23—C24−176.6 (4)
C26—N8—C27—C323.9 (6)C21—C22—C23—C24−0.4 (7)
O1—C1—C2—N2−1.8 (6)C22—C23—C24—C25−1.3 (6)
O1—C1—C2—C3177.7 (3)C23—C24—C25—N5−177.7 (4)
N1—C1—C2—N2179.6 (3)C23—C24—C25—C202.0 (6)
N1—C1—C2—C3−1.0 (3)N8—C27—C28—C29−178.4 (3)
C1—C2—C3—C4178.2 (4)N8—C27—C28—C331.0 (5)
C1—C2—C3—C80.9 (4)C32—C27—C28—C290.8 (5)
N2—C2—C3—C8−179.6 (3)C32—C27—C28—C33−179.8 (3)
N2—C2—C3—C4−2.3 (6)N8—C27—C32—C31179.1 (3)
C2—C3—C8—N1−0.5 (4)C28—C27—C32—C31−0.1 (5)
C2—C3—C4—C5−177.6 (3)C27—C28—C29—C30−0.8 (5)
C8—C3—C4—C5−0.5 (5)C33—C28—C29—C30179.8 (3)
C4—C3—C8—C70.9 (5)C28—C29—C30—C310.1 (6)
C2—C3—C8—C7178.6 (3)C29—C30—C31—Cl2−178.3 (3)
C4—C3—C8—N1−178.2 (3)C29—C30—C31—C320.7 (5)
C3—C4—C5—O2174.5 (3)Cl2—C31—C32—C27178.3 (3)
C3—C4—C5—C60.3 (5)C30—C31—C32—C27−0.6 (5)
D—H···AD—HH···AD···AD—H···A
N1—H1···O3viii0.86002.18002.937 (3)147.00
N3—H3···O10.86002.21002.841 (3)131.00
N4—H4A···N20.86002.09002.553 (4)113.00
N5—H5···S1ix0.86002.64003.287 (3)133.00
N7—H7A···O30.86002.22002.863 (3)132.00
N8—H8···N60.86002.06002.546 (3)115.00
C12—H12···F6vi0.93002.47003.284 (6)147.00
C15—H15···S10.93002.87003.325 (3)111.00
C21—H21···F50.93002.38002.930 (5)118.00
C32—H32···S20.93002.57003.245 (4)130.00
C33—H33C···O10.96002.40003.355 (4)176.00
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O3i0.86002.18002.937 (3)147.00
N3—H3⋯O10.86002.21002.841 (3)131.00
N4—H4A⋯N20.86002.09002.553 (4)113.00
N5—H5⋯S1ii0.86002.64003.287 (3)133.00
N7—H7A⋯O30.86002.22002.863 (3)132.00
N8—H8⋯N60.86002.06002.546 (3)115.00
C12—H12⋯F6iii0.93002.47003.284 (6)147.00
C15—H15⋯S10.93002.87003.325 (3)111.00
C21—H21⋯F50.93002.38002.930 (5)118.00
C32—H32⋯S20.93002.57003.245 (4)130.00
C33—H33C⋯O10.96002.40003.355 (4)176.00

Symmetry codes: (i) ; (ii) ; (iii) .

  7 in total

1.  A short history of SHELX.

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

2.  Synthesis and biological evaluation of some new N(4)-substituted isatin-3-thiosemicarbazones.

Authors:  Humayun Pervez; Zahid Hussain Chohan; Muhammad Ramzan; Faiz-Ul-Hassan Nasim; Khalid Mohammed Khan
Journal:  J Enzyme Inhib Med Chem       Date:  2009-04       Impact factor: 5.051

3.  Synthesis of some N4-substituted isatin-3-thiosemicarbazones.

Authors:  H Pervez; M S Iqbal; M Y Tahir; M I Choudhary; K M Khan
Journal:  Nat Prod Res       Date:  2007-11       Impact factor: 2.861

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

Authors:  Humayun Pervez; Muhammad Yaqub; Muhammad Ramzan; Mohammad S Iqbal; M Nawaz Tahir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-02

5.  In vitro cytotoxic, antibacterial, antifungal and urease inhibitory activities of some N4- substituted isatin-3-thiosemicarbazones.

Authors:  Humayun Pervez; Mohammad S Iqbal; Muhammad Younas Tahir; Faiz-ul-Hassan Nasim; Muhammad Iqbal Choudhary; Khalid Mohammed Khan
Journal:  J Enzyme Inhib Med Chem       Date:  2008-12       Impact factor: 5.051

6.  1-(5-Nitro-2-oxoindolin-3-yl-idene)-4-o-tolyl-thio-semicarbazide methanol monosolvate.

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

7.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  7 in total
  5 in total

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

Authors:  Humayun Pervez; Mohammad S Iqbal; Naveeda Saira; Muhammad Yaqub; M Nawaz Tahir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-23

2.  N-{2-[N-(4-Methyl-phen-yl)oxamo-yl]phen-yl}propanamide.

Authors:  Humayun Pervez; Maqbool Ahmad; Muhammad Yaqub; M Nawaz Tahir; Naveeda Saira
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-23

3.  [(Pyrrolidin-1-yl)carbothio-ylsulfan-yl]methyl pyrrolidine-1-carbodithio-ate.

Authors:  Wei-Lung Chou; Kuang-Hway Yih; Gene-Hsiang Lee; Yen-Hsiang Huang; Hsiao-Fen Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-17

4.  1-[1-(4-Bromo-phen-yl)ethyl-idene]-4-(2,4-dimeth-oxy-phen-yl)thio-semicarbazide.

Authors:  Muhammad Yaqub; Humayun Pervez; Nadia Arif; M Nawaz Tahir; Mazhar Hussain
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-18

5.  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
  5 in total

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