






Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810021264/bq2219sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810021264/bq2219Isup2.hkl |
CCDC reference: 786555
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.092
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 -- C9 .. 6.17 su PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 3 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 25 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a hot solution of isatin (0.74 g, 5.0 mmol) in ethanol (10 ml) containing a few drops of glacial acetic acid was added 4-(2-ethylphenyl)thiosemicarbazide (0.98 g, 5.0 mmol) dissolved in ethanol (10 ml) under stirring. The reaction mixture was then heated under reflux for 2 h. The yellow crystalline solid formed during heating was collected by suction filtration. Thorough washing with hot ethanol followed by ether afforded the target compound (I) in pure form (1.42 g, 88%), m. p. 485 K (d). The single crystals of (I) were grown in ethyl acetate by slow evaporation at room temperature.
The H-atoms were positioned geometrically (N–H = 0.86 Å, C–H = 0.93–0.97 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl and x = 1.2 for all other H-atoms.
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).
C17H16N4OS | F(000) = 1360 |
Mr = 324.40 | Dx = 1.364 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2400 reflections |
a = 25.6769 (7) Å | θ = 2.9–25.3° |
b = 7.4340 (2) Å | µ = 0.22 mm−1 |
c = 16.6548 (5) Å | T = 296 K |
β = 96.248 (1)° | Prism, yellow |
V = 3160.22 (15) Å3 | 0.32 × 0.24 × 0.22 mm |
Z = 8 |
Bruker Kappa APEXII CCD diffractometer | 2823 independent reflections |
Radiation source: fine-focus sealed tube | 2400 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 8.10 pixels mm-1 | θmax = 25.3°, θmin = 2.9° |
ω scans | h = −30→30 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −7→8 |
Tmin = 0.942, Tmax = 0.952 | l = −19→19 |
11310 measured reflections |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0406P)2 + 2.640P] where P = (Fo2 + 2Fc2)/3 |
2823 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C17H16N4OS | V = 3160.22 (15) Å3 |
Mr = 324.40 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.6769 (7) Å | µ = 0.22 mm−1 |
b = 7.4340 (2) Å | T = 296 K |
c = 16.6548 (5) Å | 0.32 × 0.24 × 0.22 mm |
β = 96.248 (1)° |
Bruker Kappa APEXII CCD diffractometer | 2823 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2400 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.952 | Rint = 0.022 |
11310 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.16 e Å−3 |
2823 reflections | Δρmin = −0.18 e Å−3 |
209 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.23890 (2) | −0.14366 (7) | 0.38931 (2) | 0.0442 (2) | |
O1 | 0.06872 (4) | −0.02675 (19) | 0.27866 (7) | 0.0479 (4) | |
N1 | 0.02670 (5) | 0.0792 (2) | 0.15804 (8) | 0.0442 (5) | |
N2 | 0.16415 (5) | 0.02887 (19) | 0.19012 (8) | 0.0349 (4) | |
N3 | 0.17539 (5) | −0.03419 (19) | 0.26578 (8) | 0.0372 (4) | |
N4 | 0.26102 (5) | −0.0071 (2) | 0.24633 (8) | 0.0393 (4) | |
C1 | 0.06870 (6) | 0.0291 (2) | 0.20906 (10) | 0.0381 (5) | |
C2 | 0.04184 (6) | 0.1426 (2) | 0.08419 (10) | 0.0391 (5) | |
C3 | 0.01121 (7) | 0.2144 (3) | 0.01920 (11) | 0.0516 (6) | |
C4 | 0.03640 (8) | 0.2668 (3) | −0.04645 (11) | 0.0547 (7) | |
C5 | 0.09005 (8) | 0.2485 (3) | −0.04709 (11) | 0.0495 (6) | |
C6 | 0.12070 (7) | 0.1798 (2) | 0.01934 (9) | 0.0409 (5) | |
C7 | 0.09608 (6) | 0.1274 (2) | 0.08544 (9) | 0.0341 (5) | |
C8 | 0.11566 (6) | 0.0567 (2) | 0.16408 (9) | 0.0333 (5) | |
C9 | 0.22671 (6) | −0.0580 (2) | 0.29697 (9) | 0.0342 (5) | |
C10 | 0.31682 (6) | −0.0090 (2) | 0.25921 (10) | 0.0365 (5) | |
C11 | 0.34405 (6) | −0.0684 (2) | 0.19598 (10) | 0.0392 (5) | |
C12 | 0.39859 (7) | −0.0623 (3) | 0.20944 (12) | 0.0511 (7) | |
C13 | 0.42445 (7) | 0.0001 (3) | 0.28101 (13) | 0.0585 (7) | |
C14 | 0.39670 (7) | 0.0588 (3) | 0.34154 (12) | 0.0546 (7) | |
C15 | 0.34255 (7) | 0.0550 (3) | 0.33083 (11) | 0.0452 (6) | |
C16 | 0.31486 (8) | −0.1327 (3) | 0.11775 (11) | 0.0495 (6) | |
C17 | 0.34737 (10) | −0.2230 (3) | 0.05832 (13) | 0.0717 (9) | |
H1 | −0.00519 | 0.07323 | 0.16915 | 0.0531* | |
H3 | −0.02481 | 0.22716 | 0.01929 | 0.0619* | |
H3A | 0.15051 | −0.05950 | 0.29454 | 0.0446* | |
H4 | 0.01673 | 0.31566 | −0.09139 | 0.0656* | |
H4A | 0.24765 | 0.03177 | 0.19999 | 0.0471* | |
H5 | 0.10561 | 0.28267 | −0.09261 | 0.0594* | |
H6 | 0.15681 | 0.16924 | 0.01957 | 0.0490* | |
H12 | 0.41813 | −0.10153 | 0.16896 | 0.0613* | |
H13 | 0.46088 | 0.00228 | 0.28809 | 0.0702* | |
H14 | 0.41418 | 0.10101 | 0.38969 | 0.0655* | |
H15 | 0.32347 | 0.09524 | 0.37168 | 0.0543* | |
H16A | 0.29714 | −0.03025 | 0.09104 | 0.0595* | |
H16B | 0.28807 | −0.21671 | 0.13056 | 0.0595* | |
H17A | 0.37156 | −0.13760 | 0.04015 | 0.1076* | |
H17B | 0.32467 | −0.26665 | 0.01289 | 0.1076* | |
H17C | 0.36643 | −0.32188 | 0.08436 | 0.1076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0421 (3) | 0.0538 (3) | 0.0371 (2) | 0.0059 (2) | 0.0058 (2) | 0.0088 (2) |
O1 | 0.0369 (6) | 0.0701 (9) | 0.0379 (7) | 0.0024 (6) | 0.0097 (5) | 0.0099 (6) |
N1 | 0.0265 (7) | 0.0667 (10) | 0.0396 (8) | −0.0015 (7) | 0.0045 (6) | 0.0036 (7) |
N2 | 0.0306 (7) | 0.0406 (8) | 0.0334 (7) | 0.0011 (6) | 0.0036 (5) | 0.0002 (6) |
N3 | 0.0290 (7) | 0.0488 (9) | 0.0345 (7) | 0.0018 (6) | 0.0061 (5) | 0.0052 (6) |
N4 | 0.0294 (7) | 0.0548 (9) | 0.0339 (7) | 0.0038 (6) | 0.0043 (5) | 0.0074 (6) |
C1 | 0.0321 (8) | 0.0449 (10) | 0.0379 (9) | −0.0012 (7) | 0.0060 (7) | −0.0007 (7) |
C2 | 0.0345 (8) | 0.0455 (10) | 0.0368 (8) | −0.0021 (7) | 0.0013 (7) | −0.0010 (7) |
C3 | 0.0384 (9) | 0.0649 (13) | 0.0495 (10) | 0.0047 (9) | −0.0042 (8) | 0.0045 (9) |
C4 | 0.0584 (12) | 0.0610 (13) | 0.0418 (10) | 0.0041 (10) | −0.0071 (9) | 0.0092 (9) |
C5 | 0.0600 (12) | 0.0511 (12) | 0.0378 (9) | −0.0038 (9) | 0.0069 (8) | 0.0048 (8) |
C6 | 0.0425 (9) | 0.0449 (10) | 0.0356 (9) | −0.0032 (8) | 0.0063 (7) | −0.0013 (7) |
C7 | 0.0331 (8) | 0.0358 (9) | 0.0329 (8) | −0.0007 (7) | 0.0020 (6) | −0.0035 (7) |
C8 | 0.0304 (8) | 0.0374 (9) | 0.0325 (8) | −0.0002 (7) | 0.0049 (6) | −0.0018 (7) |
C9 | 0.0314 (8) | 0.0344 (9) | 0.0372 (9) | 0.0042 (6) | 0.0053 (6) | −0.0032 (7) |
C10 | 0.0317 (8) | 0.0386 (9) | 0.0394 (9) | 0.0028 (7) | 0.0054 (7) | 0.0084 (7) |
C11 | 0.0408 (9) | 0.0359 (9) | 0.0424 (9) | 0.0052 (7) | 0.0118 (7) | 0.0102 (7) |
C12 | 0.0419 (10) | 0.0567 (12) | 0.0583 (12) | 0.0099 (9) | 0.0214 (9) | 0.0154 (9) |
C13 | 0.0308 (9) | 0.0763 (15) | 0.0682 (13) | −0.0005 (9) | 0.0051 (9) | 0.0178 (11) |
C14 | 0.0410 (10) | 0.0684 (14) | 0.0523 (11) | −0.0099 (9) | −0.0040 (8) | 0.0095 (10) |
C15 | 0.0391 (9) | 0.0541 (11) | 0.0426 (10) | −0.0009 (8) | 0.0048 (7) | 0.0029 (8) |
C16 | 0.0587 (11) | 0.0465 (11) | 0.0448 (10) | 0.0051 (9) | 0.0119 (8) | 0.0032 (8) |
C17 | 0.0976 (17) | 0.0655 (15) | 0.0572 (13) | −0.0001 (13) | 0.0317 (12) | −0.0070 (11) |
S1—C9 | 1.6625 (15) | C10—C15 | 1.384 (2) |
O1—C1 | 1.231 (2) | C11—C16 | 1.508 (3) |
N1—C1 | 1.351 (2) | C11—C12 | 1.395 (2) |
N1—C2 | 1.411 (2) | C12—C13 | 1.380 (3) |
N2—N3 | 1.3460 (19) | C13—C14 | 1.368 (3) |
N2—C8 | 1.290 (2) | C14—C15 | 1.383 (3) |
N3—C9 | 1.374 (2) | C16—C17 | 1.519 (3) |
N4—C9 | 1.339 (2) | C3—H3 | 0.9300 |
N4—C10 | 1.426 (2) | C4—H4 | 0.9300 |
N1—H1 | 0.8600 | C5—H5 | 0.9300 |
N3—H3A | 0.8600 | C6—H6 | 0.9300 |
N4—H4A | 0.8600 | C12—H12 | 0.9300 |
C1—C8 | 1.501 (2) | C13—H13 | 0.9300 |
C2—C7 | 1.395 (2) | C14—H14 | 0.9300 |
C2—C3 | 1.375 (2) | C15—H15 | 0.9300 |
C3—C4 | 1.386 (3) | C16—H16A | 0.9700 |
C4—C5 | 1.386 (3) | C16—H16B | 0.9700 |
C5—C6 | 1.384 (2) | C17—H17A | 0.9600 |
C6—C7 | 1.384 (2) | C17—H17B | 0.9600 |
C7—C8 | 1.450 (2) | C17—H17C | 0.9600 |
C10—C11 | 1.398 (2) | ||
S1···C15 | 3.283 (2) | C1···H1iii | 2.7600 |
S1···N4i | 3.5220 (15) | C1···H3A | 2.4900 |
S1···H15 | 2.8500 | C5···H17Avii | 3.0500 |
S1···H6ii | 3.1900 | C9···H15 | 2.8900 |
S1···H4Ai | 2.8700 | C9···H16Biv | 2.8500 |
S1···H16Ai | 3.0500 | C12···H5vii | 2.8400 |
O1···N2 | 3.0226 (17) | C12···H17A | 2.8800 |
O1···N3 | 2.7711 (17) | C12···H17C | 2.8900 |
O1···C5ii | 3.331 (2) | C16···H4A | 2.6200 |
O1···N1iii | 2.8805 (17) | C17···H12 | 2.6000 |
O1···H1iii | 2.0700 | H1···O1iii | 2.0700 |
O1···H3A | 2.1000 | H1···C1iii | 2.7600 |
N1···O1iii | 2.8805 (17) | H3A···O1 | 2.1000 |
N2···O1 | 3.0226 (17) | H3A···C1 | 2.4900 |
N2···N4 | 2.5745 (18) | H4A···N2 | 2.1300 |
N3···O1 | 2.7711 (17) | H4A···C16 | 2.6200 |
N4···C9iv | 3.437 (2) | H4A···H16A | 2.3700 |
N4···N2 | 2.5745 (18) | H4A···H16B | 2.4700 |
N4···S1iv | 3.5220 (15) | H4A···S1iv | 2.8700 |
N2···H4A | 2.1300 | H5···C12vii | 2.8400 |
N4···H16B | 2.6300 | H6···S1vi | 3.1900 |
N4···H16A | 2.8500 | H12···C17 | 2.6000 |
C1···C13iv | 3.509 (3) | H12···H17A | 2.3500 |
C1···C12iv | 3.395 (3) | H12···H17C | 2.4500 |
C2···C3v | 3.370 (3) | H13···H13viii | 2.4900 |
C2···C13iv | 3.526 (3) | H15···S1 | 2.8500 |
C3···C3v | 3.290 (3) | H15···C9 | 2.8900 |
C3···C2v | 3.370 (3) | H16A···N4 | 2.8500 |
C5···O1vi | 3.331 (2) | H16A···H4A | 2.3700 |
C7···C14iv | 3.428 (3) | H16A···S1iv | 3.0500 |
C8···C12iv | 3.572 (3) | H16B···N4 | 2.6300 |
C9···N4i | 3.437 (2) | H16B···H4A | 2.4700 |
C12···C8i | 3.572 (3) | H16B···C9i | 2.8500 |
C12···C1i | 3.395 (3) | H17A···C12 | 2.8800 |
C13···C2i | 3.526 (3) | H17A···H12 | 2.3500 |
C13···C1i | 3.509 (3) | H17A···C5vii | 3.0500 |
C14···C7i | 3.428 (3) | H17C···C12 | 2.8900 |
C15···S1 | 3.283 (2) | H17C···H12 | 2.4500 |
C1—N1—C2 | 111.33 (13) | C12—C11—C16 | 123.02 (16) |
N3—N2—C8 | 118.13 (13) | C11—C12—C13 | 122.01 (17) |
N2—N3—C9 | 119.86 (13) | C12—C13—C14 | 120.24 (17) |
C9—N4—C10 | 128.46 (14) | C13—C14—C15 | 119.71 (18) |
C2—N1—H1 | 124.00 | C10—C15—C14 | 119.83 (17) |
C1—N1—H1 | 124.00 | C11—C16—C17 | 116.51 (17) |
C9—N3—H3A | 120.00 | C2—C3—H3 | 121.00 |
N2—N3—H3A | 120.00 | C4—C3—H3 | 121.00 |
C9—N4—H4A | 116.00 | C3—C4—H4 | 119.00 |
C10—N4—H4A | 116.00 | C5—C4—H4 | 119.00 |
O1—C1—N1 | 127.14 (14) | C4—C5—H5 | 120.00 |
O1—C1—C8 | 126.71 (14) | C6—C5—H5 | 120.00 |
N1—C1—C8 | 106.14 (13) | C5—C6—H6 | 121.00 |
N1—C2—C7 | 109.23 (13) | C7—C6—H6 | 121.00 |
C3—C2—C7 | 121.86 (15) | C11—C12—H12 | 119.00 |
N1—C2—C3 | 128.89 (15) | C13—C12—H12 | 119.00 |
C2—C3—C4 | 117.02 (17) | C12—C13—H13 | 120.00 |
C3—C4—C5 | 121.90 (18) | C14—C13—H13 | 120.00 |
C4—C5—C6 | 120.63 (17) | C13—C14—H14 | 120.00 |
C5—C6—C7 | 118.08 (17) | C15—C14—H14 | 120.00 |
C2—C7—C6 | 120.47 (15) | C10—C15—H15 | 120.00 |
C2—C7—C8 | 106.88 (13) | C14—C15—H15 | 120.00 |
C6—C7—C8 | 132.64 (15) | C11—C16—H16A | 108.00 |
N2—C8—C7 | 126.10 (14) | C11—C16—H16B | 108.00 |
N2—C8—C1 | 127.49 (14) | C17—C16—H16A | 108.00 |
C1—C8—C7 | 106.38 (13) | C17—C16—H16B | 108.00 |
S1—C9—N3 | 118.38 (12) | H16A—C16—H16B | 107.00 |
S1—C9—N4 | 128.35 (12) | C16—C17—H17A | 109.00 |
N3—C9—N4 | 113.27 (13) | C16—C17—H17B | 109.00 |
C11—C10—C15 | 121.82 (15) | C16—C17—H17C | 109.00 |
N4—C10—C15 | 120.28 (15) | H17A—C17—H17B | 109.00 |
N4—C10—C11 | 117.83 (14) | H17A—C17—H17C | 109.00 |
C10—C11—C12 | 116.40 (15) | H17B—C17—H17C | 109.00 |
C10—C11—C16 | 120.58 (15) | ||
C1—N1—C2—C3 | −176.03 (18) | C2—C3—C4—C5 | −0.1 (3) |
C2—N1—C1—O1 | 177.74 (16) | C3—C4—C5—C6 | −1.3 (3) |
C2—N1—C1—C8 | −1.78 (17) | C4—C5—C6—C7 | 1.1 (3) |
C1—N1—C2—C7 | 2.28 (18) | C5—C6—C7—C8 | −177.87 (17) |
N3—N2—C8—C7 | 178.61 (14) | C5—C6—C7—C2 | 0.5 (2) |
C8—N2—N3—C9 | −177.12 (14) | C2—C7—C8—N2 | −177.51 (15) |
N3—N2—C8—C1 | 0.9 (2) | C6—C7—C8—N2 | 1.1 (3) |
N2—N3—C9—S1 | −177.65 (12) | C6—C7—C8—C1 | 179.21 (16) |
N2—N3—C9—N4 | 2.2 (2) | C2—C7—C8—C1 | 0.65 (16) |
C10—N4—C9—S1 | −1.7 (3) | N4—C10—C11—C12 | 177.69 (16) |
C9—N4—C10—C15 | −45.5 (2) | N4—C10—C11—C16 | −1.6 (2) |
C10—N4—C9—N3 | 178.48 (15) | C15—C10—C11—C12 | 1.0 (2) |
C9—N4—C10—C11 | 137.74 (17) | C15—C10—C11—C16 | −178.32 (17) |
O1—C1—C8—N2 | −0.7 (3) | N4—C10—C15—C14 | −177.59 (18) |
O1—C1—C8—C7 | −178.83 (16) | C11—C10—C15—C14 | −0.9 (3) |
N1—C1—C8—N2 | 178.80 (16) | C10—C11—C12—C13 | −0.4 (3) |
N1—C1—C8—C7 | 0.68 (16) | C16—C11—C12—C13 | 178.81 (19) |
N1—C2—C3—C4 | 179.90 (17) | C10—C11—C16—C17 | −170.19 (16) |
C7—C2—C3—C4 | 1.8 (3) | C12—C11—C16—C17 | 10.6 (3) |
N1—C2—C7—C6 | 179.51 (14) | C11—C12—C13—C14 | −0.1 (3) |
N1—C2—C7—C8 | −1.72 (17) | C12—C13—C14—C15 | 0.2 (3) |
C3—C2—C7—C6 | −2.0 (2) | C13—C14—C15—C10 | 0.4 (3) |
C3—C2—C7—C8 | 176.74 (16) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, −y, z+1/2; (iii) −x, y, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2; (v) −x, −y, −z; (vi) x, −y, z−1/2; (vii) −x+1/2, −y+1/2, −z; (viii) −x+1, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1iii | 0.8600 | 2.0700 | 2.8805 (17) | 157.00 |
N3—H3A···O1 | 0.8600 | 2.1000 | 2.7711 (17) | 134.00 |
N4—H4A···N2 | 0.8600 | 2.1300 | 2.5745 (18) | 111.00 |
N4—H4A···S1iv | 0.8600 | 2.8700 | 3.5220 (15) | 133.00 |
C15—H15···S1 | 0.9300 | 2.8500 | 3.283 (2) | 110.00 |
Symmetry codes: (iii) −x, y, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H16N4OS |
Mr | 324.40 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 25.6769 (7), 7.4340 (2), 16.6548 (5) |
β (°) | 96.248 (1) |
V (Å3) | 3160.22 (15) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.32 × 0.24 × 0.22 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.942, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11310, 2823, 2400 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.092, 1.04 |
No. of reflections | 2823 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.18 |
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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.8600 | 2.0700 | 2.8805 (17) | 157.00 |
N3—H3A···O1 | 0.8600 | 2.1000 | 2.7711 (17) | 134.00 |
N4—H4A···N2 | 0.8600 | 2.1300 | 2.5745 (18) | 111.00 |
N4—H4A···S1ii | 0.8600 | 2.8700 | 3.5220 (15) | 133.00 |
C15—H15···S1 | 0.9300 | 2.8500 | 3.283 (2) | 110.00 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2. |
The title compound (I), (Fig 1) is being reported in continuation of synthesizing biologically important isatin derivatives (Pervez et al., 2007).
The crystal structure of (II) i.e. 4-(2-fluorophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide (Pervez et al., 2010) has been published. The title compound (I) differs from (II) due to the attachment of ethyl instead of fluoro group at position-2 of the phenyl ring substituted at N4 of the thiosemicarbazone moiety.
In (I) the 2-oxoindolin A (C1–C8/N1/O1), thiosemicarbazide B (N2/N3/C9/S1/N4) and phenyl ring of 2-ethylphenyl C (C10—C16) are planar with r. m. s. deviations of 0.0178, 0.0244 and 0.0149 Å, respectively. The dihedral angle between A/B, A/C and B/C is 8.71 (5)°, 33.59 (3)° and 39.32 (3)°, 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 interlinked through N—H···O and N–H···S intermolecular H-bondings. Due to these interactions infinite two-dimensional polymeric network exists. There exist π···π interaction at a distance of 3.6514 (10) Å between the benzene ring (C10—C15) and the heterocyclic ring (N1/C7/C2/C1/C8).