organic compounds
1-(1-Decyl-2-oxoindolin-3-ylidene)thiosemicarbazide
aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, bLaboratoire de Chimie Organique et Etudes Physicochimiques, ENS Rabat, Morocco, cCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
In the title 1-alkylisatin 3-thiosemicarbazone, C19H28N4OS, the imine C=N bond has a Z configuration, whereas the N—N—C=S unit has an E conformation. In the crystal, molecules are connected by N—H⋯O hydrogen bonds, forming zigzag chains running along the b axis.
Related literature
For background to N-substituted isatins and their derivatives, see: Bouhfid et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536810016521/bt5265sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016521/bt5265Isup2.hkl
1-Decyl-isatin (1 g, 3.1 mmol) and thiosemicarbazide (0.31 g, 3.4 mmol) were dissolved in aqueous ethanol (50 ml); a few drops of glacial acetic acid were added. The mixture was heated for 4 hours. Yellow crystals separated from the cool solution in 80% yield.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C). The amino-H atoms were located in a difference Fourier map, and they were refined isotropically with the N–H distance restrained to 0.86±0.01 Å.N-Substituted isatins (Bouhfid et al., 2008) represent a large family of
reported to show a wide range of useful medicinal properties. These condense readily with thiosemicarbazides to form crystalline thiosemicarbazones. The title 1-decylisatin derivative has a Z configuration around the imine C=N bond and E configuration the C(=S)–NH2 bond (Scheme I, Fig. 1). The molecules form zigzag chains though N–H···O hydrogen bonds along the b-axis of the monoclinic (Fig. 2). The decyl chain adopts an irregular zigzag conformation; the irregular nature lead to a compact packing and there are no voids in the crystal.For background to N-substituted isatins and their derivatives, see: Bouhfid et al. (2008).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).C19H28N4OS | F(000) = 776 |
Mr = 360.51 | Dx = 1.224 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5658 reflections |
a = 11.8856 (2) Å | θ = 2.3–28.7° |
b = 11.0055 (2) Å | µ = 0.18 mm−1 |
c = 15.1638 (3) Å | T = 180 K |
β = 99.468 (1)° | Prism, yellow |
V = 1956.51 (6) Å3 | 0.23 × 0.14 × 0.12 mm |
Z = 4 |
Bruker X8 APEXII diffractometer | 5715 independent reflections |
Radiation source: fine-focus sealed tube | 4227 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 30.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.960, Tmax = 0.979 | k = −13→15 |
26304 measured reflections | l = −18→21 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0721P)2 + 0.276P] where P = (Fo2 + 2Fc2)/3 |
5715 reflections | (Δ/σ)max = 0.001 |
238 parameters | Δρmax = 0.30 e Å−3 |
3 restraints | Δρmin = −0.36 e Å−3 |
C19H28N4OS | V = 1956.51 (6) Å3 |
Mr = 360.51 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.8856 (2) Å | µ = 0.18 mm−1 |
b = 11.0055 (2) Å | T = 180 K |
c = 15.1638 (3) Å | 0.23 × 0.14 × 0.12 mm |
β = 99.468 (1)° |
Bruker X8 APEXII diffractometer | 5715 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4227 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.979 | Rint = 0.043 |
26304 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 3 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.30 e Å−3 |
5715 reflections | Δρmin = −0.36 e Å−3 |
238 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.80459 (3) | 0.78130 (4) | 0.66953 (3) | 0.03232 (12) | |
O1 | 0.66844 (10) | 0.67702 (9) | 0.91795 (7) | 0.0330 (3) | |
N1 | 0.78312 (11) | 1.00870 (12) | 0.72565 (9) | 0.0304 (3) | |
N2 | 0.73941 (11) | 0.85612 (11) | 0.81634 (8) | 0.0277 (3) | |
N3 | 0.71786 (10) | 0.93926 (10) | 0.87721 (8) | 0.0241 (2) | |
N4 | 0.61721 (10) | 0.76378 (10) | 1.04405 (8) | 0.0232 (2) | |
C1 | 0.77480 (11) | 0.89065 (12) | 0.73872 (9) | 0.0240 (3) | |
C2 | 0.68081 (11) | 0.89632 (12) | 0.94641 (9) | 0.0221 (3) | |
C3 | 0.65089 (11) | 0.96609 (12) | 1.02047 (9) | 0.0214 (3) | |
C4 | 0.65109 (12) | 1.08920 (12) | 1.03890 (10) | 0.0250 (3) | |
H4 | 0.6761 | 1.1465 | 0.9994 | 0.030* | |
C5 | 0.61370 (12) | 1.12684 (13) | 1.11687 (10) | 0.0289 (3) | |
H5 | 0.6136 | 1.2109 | 1.1310 | 0.035* | |
C6 | 0.57670 (12) | 1.04303 (14) | 1.17397 (10) | 0.0296 (3) | |
H6 | 0.5518 | 1.0710 | 1.2268 | 0.035* | |
C7 | 0.57503 (12) | 0.91890 (13) | 1.15612 (9) | 0.0266 (3) | |
H7 | 0.5491 | 0.8618 | 1.1953 | 0.032* | |
C8 | 0.61282 (11) | 0.88257 (11) | 1.07871 (9) | 0.0214 (3) | |
C9 | 0.65662 (12) | 0.76577 (12) | 0.96510 (9) | 0.0240 (3) | |
C10 | 0.58378 (12) | 0.65187 (12) | 1.08470 (10) | 0.0258 (3) | |
H10A | 0.5452 | 0.5974 | 1.0372 | 0.031* | |
H10B | 0.5286 | 0.6716 | 1.1249 | 0.031* | |
C11 | 0.68480 (13) | 0.58614 (14) | 1.13747 (11) | 0.0329 (3) | |
H11A | 0.7232 | 0.6404 | 1.1852 | 0.040* | |
H11B | 0.7402 | 0.5667 | 1.0974 | 0.040* | |
C12 | 0.64970 (14) | 0.46857 (13) | 1.17964 (11) | 0.0319 (3) | |
H12A | 0.5931 | 0.4257 | 1.1352 | 0.038* | |
H12B | 0.7175 | 0.4154 | 1.1935 | 0.038* | |
C13 | 0.59920 (13) | 0.48675 (12) | 1.26434 (11) | 0.0305 (3) | |
H13A | 0.5286 | 0.5355 | 1.2500 | 0.037* | |
H13B | 0.6539 | 0.5334 | 1.3079 | 0.037* | |
C14 | 0.57148 (13) | 0.36767 (13) | 1.30730 (11) | 0.0314 (3) | |
H14A | 0.6407 | 0.3161 | 1.3168 | 0.038* | |
H14B | 0.5121 | 0.3243 | 1.2655 | 0.038* | |
C15 | 0.52981 (13) | 0.38398 (14) | 1.39615 (11) | 0.0321 (3) | |
H15A | 0.5876 | 0.4308 | 1.4369 | 0.039* | |
H15B | 0.4588 | 0.4326 | 1.3860 | 0.039* | |
C16 | 0.50680 (14) | 0.26574 (14) | 1.44180 (11) | 0.0341 (3) | |
H16A | 0.5792 | 0.2204 | 1.4577 | 0.041* | |
H16B | 0.4540 | 0.2153 | 1.3996 | 0.041* | |
C17 | 0.45517 (16) | 0.28689 (16) | 1.52591 (13) | 0.0431 (4) | |
H17A | 0.3889 | 0.3420 | 1.5111 | 0.052* | |
H17B | 0.5123 | 0.3286 | 1.5706 | 0.052* | |
C18 | 0.41613 (17) | 0.17156 (19) | 1.56828 (14) | 0.0511 (5) | |
H18A | 0.3704 | 0.1947 | 1.6146 | 0.061* | |
H18B | 0.3663 | 0.1242 | 1.5219 | 0.061* | |
C19 | 0.5135 (2) | 0.09282 (19) | 1.60994 (14) | 0.0567 (5) | |
H19A | 0.4836 | 0.0208 | 1.6363 | 0.085* | |
H19B | 0.5625 | 0.1386 | 1.6567 | 0.085* | |
H19C | 0.5579 | 0.0676 | 1.5641 | 0.085* | |
H11 | 0.8010 (16) | 1.0349 (19) | 0.6760 (9) | 0.048 (6)* | |
H12 | 0.7606 (16) | 1.0593 (15) | 0.7628 (11) | 0.044 (5)* | |
H2 | 0.7284 (16) | 0.7811 (10) | 0.8277 (13) | 0.044 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0421 (2) | 0.0309 (2) | 0.0277 (2) | 0.00066 (15) | 0.01700 (16) | −0.00417 (15) |
O1 | 0.0523 (7) | 0.0207 (5) | 0.0300 (6) | 0.0001 (4) | 0.0186 (5) | −0.0034 (4) |
N1 | 0.0425 (7) | 0.0262 (6) | 0.0262 (6) | 0.0024 (5) | 0.0164 (6) | 0.0043 (5) |
N2 | 0.0427 (7) | 0.0197 (5) | 0.0247 (6) | 0.0004 (5) | 0.0175 (5) | 0.0007 (5) |
N3 | 0.0297 (6) | 0.0216 (5) | 0.0227 (6) | 0.0011 (4) | 0.0095 (5) | 0.0007 (4) |
N4 | 0.0316 (6) | 0.0180 (5) | 0.0222 (6) | 0.0008 (4) | 0.0106 (5) | 0.0025 (4) |
C1 | 0.0247 (6) | 0.0266 (6) | 0.0216 (6) | 0.0011 (5) | 0.0069 (5) | 0.0015 (5) |
C2 | 0.0268 (6) | 0.0193 (6) | 0.0214 (6) | 0.0013 (5) | 0.0074 (5) | 0.0007 (5) |
C3 | 0.0242 (6) | 0.0199 (6) | 0.0207 (6) | 0.0006 (5) | 0.0052 (5) | 0.0003 (5) |
C4 | 0.0287 (7) | 0.0208 (6) | 0.0262 (7) | −0.0004 (5) | 0.0062 (5) | 0.0009 (5) |
C5 | 0.0350 (7) | 0.0226 (6) | 0.0293 (8) | 0.0010 (5) | 0.0064 (6) | −0.0063 (5) |
C6 | 0.0346 (8) | 0.0320 (7) | 0.0233 (7) | 0.0021 (6) | 0.0081 (6) | −0.0056 (6) |
C7 | 0.0323 (7) | 0.0281 (7) | 0.0209 (7) | 0.0007 (5) | 0.0087 (5) | 0.0007 (5) |
C8 | 0.0246 (6) | 0.0198 (6) | 0.0202 (6) | 0.0020 (5) | 0.0048 (5) | 0.0005 (5) |
C9 | 0.0306 (7) | 0.0204 (6) | 0.0226 (6) | 0.0006 (5) | 0.0091 (5) | 0.0015 (5) |
C10 | 0.0313 (7) | 0.0202 (6) | 0.0274 (7) | −0.0029 (5) | 0.0095 (6) | 0.0035 (5) |
C11 | 0.0336 (7) | 0.0268 (7) | 0.0400 (9) | −0.0001 (6) | 0.0107 (6) | 0.0105 (6) |
C12 | 0.0383 (8) | 0.0219 (6) | 0.0370 (8) | 0.0034 (6) | 0.0104 (7) | 0.0079 (6) |
C13 | 0.0341 (7) | 0.0207 (6) | 0.0373 (8) | −0.0011 (5) | 0.0077 (6) | 0.0058 (6) |
C14 | 0.0350 (8) | 0.0240 (7) | 0.0361 (8) | 0.0001 (6) | 0.0082 (6) | 0.0077 (6) |
C15 | 0.0345 (8) | 0.0281 (7) | 0.0345 (8) | −0.0001 (6) | 0.0076 (6) | 0.0064 (6) |
C16 | 0.0367 (8) | 0.0304 (7) | 0.0366 (9) | 0.0013 (6) | 0.0102 (7) | 0.0080 (6) |
C17 | 0.0451 (9) | 0.0427 (10) | 0.0453 (10) | 0.0034 (7) | 0.0186 (8) | 0.0095 (8) |
C18 | 0.0539 (11) | 0.0584 (12) | 0.0445 (11) | −0.0115 (9) | 0.0185 (9) | 0.0095 (9) |
C19 | 0.0836 (15) | 0.0492 (11) | 0.0392 (10) | −0.0012 (10) | 0.0159 (10) | 0.0104 (9) |
S1—C1 | 1.6723 (14) | C11—C12 | 1.531 (2) |
O1—C9 | 1.2320 (17) | C11—H11A | 0.9900 |
N1—C1 | 1.3204 (18) | C11—H11B | 0.9900 |
N1—H11 | 0.864 (9) | C12—C13 | 1.518 (2) |
N1—H12 | 0.865 (9) | C12—H12A | 0.9900 |
N2—N3 | 1.3537 (16) | C12—H12B | 0.9900 |
N2—C1 | 1.3673 (17) | C13—C14 | 1.5235 (19) |
N2—H2 | 0.858 (9) | C13—H13A | 0.9900 |
N3—C2 | 1.2924 (17) | C13—H13B | 0.9900 |
N4—C9 | 1.3556 (17) | C14—C15 | 1.521 (2) |
N4—C8 | 1.4132 (16) | C14—H14A | 0.9900 |
N4—C10 | 1.4613 (17) | C14—H14B | 0.9900 |
C2—C3 | 1.4521 (18) | C15—C16 | 1.520 (2) |
C2—C9 | 1.5014 (18) | C15—H15A | 0.9900 |
C3—C4 | 1.3833 (18) | C15—H15B | 0.9900 |
C3—C8 | 1.4004 (18) | C16—C17 | 1.521 (2) |
C4—C5 | 1.3928 (19) | C16—H16A | 0.9900 |
C4—H4 | 0.9500 | C16—H16B | 0.9900 |
C5—C6 | 1.385 (2) | C17—C18 | 1.529 (3) |
C5—H5 | 0.9500 | C17—H17A | 0.9900 |
C6—C7 | 1.392 (2) | C17—H17B | 0.9900 |
C6—H6 | 0.9500 | C18—C19 | 1.499 (3) |
C7—C8 | 1.3831 (18) | C18—H18A | 0.9900 |
C7—H7 | 0.9500 | C18—H18B | 0.9900 |
C10—C11 | 1.513 (2) | C19—H19A | 0.9800 |
C10—H10A | 0.9900 | C19—H19B | 0.9800 |
C10—H10B | 0.9900 | C19—H19C | 0.9800 |
C1—N1—H11 | 119.6 (15) | C13—C12—C11 | 114.51 (13) |
C1—N1—H12 | 119.8 (13) | C13—C12—H12A | 108.6 |
H11—N1—H12 | 119.9 (19) | C11—C12—H12A | 108.6 |
N3—N2—C1 | 121.24 (12) | C13—C12—H12B | 108.6 |
N3—N2—H2 | 117.5 (13) | C11—C12—H12B | 108.6 |
C1—N2—H2 | 121.3 (13) | H12A—C12—H12B | 107.6 |
C2—N3—N2 | 115.75 (11) | C12—C13—C14 | 113.07 (12) |
C9—N4—C8 | 110.65 (11) | C12—C13—H13A | 109.0 |
C9—N4—C10 | 122.93 (11) | C14—C13—H13A | 109.0 |
C8—N4—C10 | 126.41 (11) | C12—C13—H13B | 109.0 |
N1—C1—N2 | 116.36 (12) | C14—C13—H13B | 109.0 |
N1—C1—S1 | 125.81 (11) | H13A—C13—H13B | 107.8 |
N2—C1—S1 | 117.83 (10) | C13—C14—C15 | 113.72 (13) |
N3—C2—C3 | 126.45 (12) | C13—C14—H14A | 108.8 |
N3—C2—C9 | 127.20 (12) | C15—C14—H14A | 108.8 |
C3—C2—C9 | 106.33 (11) | C13—C14—H14B | 108.8 |
C4—C3—C8 | 120.36 (12) | C15—C14—H14B | 108.8 |
C4—C3—C2 | 132.97 (12) | H14A—C14—H14B | 107.7 |
C8—C3—C2 | 106.64 (11) | C16—C15—C14 | 114.32 (13) |
C3—C4—C5 | 118.21 (13) | C16—C15—H15A | 108.7 |
C3—C4—H4 | 120.9 | C14—C15—H15A | 108.7 |
C5—C4—H4 | 120.9 | C16—C15—H15B | 108.7 |
C6—C5—C4 | 120.72 (13) | C14—C15—H15B | 108.7 |
C6—C5—H5 | 119.6 | H15A—C15—H15B | 107.6 |
C4—C5—H5 | 119.6 | C15—C16—C17 | 112.24 (14) |
C5—C6—C7 | 121.85 (13) | C15—C16—H16A | 109.2 |
C5—C6—H6 | 119.1 | C17—C16—H16A | 109.2 |
C7—C6—H6 | 119.1 | C15—C16—H16B | 109.2 |
C8—C7—C6 | 116.91 (13) | C17—C16—H16B | 109.2 |
C8—C7—H7 | 121.5 | H16A—C16—H16B | 107.9 |
C6—C7—H7 | 121.5 | C16—C17—C18 | 114.67 (16) |
C7—C8—C3 | 121.95 (12) | C16—C17—H17A | 108.6 |
C7—C8—N4 | 128.32 (12) | C18—C17—H17A | 108.6 |
C3—C8—N4 | 109.70 (11) | C16—C17—H17B | 108.6 |
O1—C9—N4 | 126.06 (12) | C18—C17—H17B | 108.6 |
O1—C9—C2 | 127.26 (12) | H17A—C17—H17B | 107.6 |
N4—C9—C2 | 106.67 (11) | C19—C18—C17 | 112.98 (16) |
N4—C10—C11 | 112.26 (12) | C19—C18—H18A | 109.0 |
N4—C10—H10A | 109.2 | C17—C18—H18A | 109.0 |
C11—C10—H10A | 109.2 | C19—C18—H18B | 109.0 |
N4—C10—H10B | 109.2 | C17—C18—H18B | 109.0 |
C11—C10—H10B | 109.2 | H18A—C18—H18B | 107.8 |
H10A—C10—H10B | 107.9 | C18—C19—H19A | 109.5 |
C10—C11—C12 | 112.20 (12) | C18—C19—H19B | 109.5 |
C10—C11—H11A | 109.2 | H19A—C19—H19B | 109.5 |
C12—C11—H11A | 109.2 | C18—C19—H19C | 109.5 |
C10—C11—H11B | 109.2 | H19A—C19—H19C | 109.5 |
C12—C11—H11B | 109.2 | H19B—C19—H19C | 109.5 |
H11A—C11—H11B | 107.9 | ||
C1—N2—N3—C2 | 177.49 (13) | C10—N4—C8—C7 | −1.2 (2) |
N3—N2—C1—N1 | −2.0 (2) | C9—N4—C8—C3 | −0.06 (16) |
N3—N2—C1—S1 | 177.49 (10) | C10—N4—C8—C3 | −179.47 (12) |
N2—N3—C2—C3 | −179.58 (13) | C8—N4—C9—O1 | −178.82 (14) |
N2—N3—C2—C9 | −1.7 (2) | C10—N4—C9—O1 | 0.6 (2) |
N3—C2—C3—C4 | 0.7 (2) | C8—N4—C9—C2 | 0.34 (15) |
C9—C2—C3—C4 | −177.54 (15) | C10—N4—C9—C2 | 179.77 (12) |
N3—C2—C3—C8 | 178.72 (13) | N3—C2—C9—O1 | 0.4 (2) |
C9—C2—C3—C8 | 0.44 (14) | C3—C2—C9—O1 | 178.66 (14) |
C8—C3—C4—C5 | 0.6 (2) | N3—C2—C9—N4 | −178.74 (13) |
C2—C3—C4—C5 | 178.39 (14) | C3—C2—C9—N4 | −0.48 (15) |
C3—C4—C5—C6 | −0.4 (2) | C9—N4—C10—C11 | 83.30 (17) |
C4—C5—C6—C7 | −0.1 (2) | C8—N4—C10—C11 | −97.36 (16) |
C5—C6—C7—C8 | 0.4 (2) | N4—C10—C11—C12 | −179.72 (12) |
C6—C7—C8—C3 | −0.2 (2) | C10—C11—C12—C13 | −78.90 (18) |
C6—C7—C8—N4 | −178.24 (14) | C11—C12—C13—C14 | −176.76 (13) |
C4—C3—C8—C7 | −0.4 (2) | C12—C13—C14—C15 | 175.33 (13) |
C2—C3—C8—C7 | −178.65 (12) | C13—C14—C15—C16 | −177.44 (13) |
C4—C3—C8—N4 | 178.04 (12) | C14—C15—C16—C17 | −174.78 (14) |
C2—C3—C8—N4 | −0.25 (15) | C15—C16—C17—C18 | 172.62 (15) |
C9—N4—C8—C7 | 178.21 (14) | C16—C17—C18—C19 | 69.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H12···S1i | 0.87 (1) | 2.81 (1) | 3.628 (1) | 159 (2) |
N1—H11···O1i | 0.86 (1) | 2.19 (1) | 2.986 (2) | 154 (2) |
Symmetry code: (i) −x+3/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C19H28N4OS |
Mr | 360.51 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 180 |
a, b, c (Å) | 11.8856 (2), 11.0055 (2), 15.1638 (3) |
β (°) | 99.468 (1) |
V (Å3) | 1956.51 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.23 × 0.14 × 0.12 |
Data collection | |
Diffractometer | Bruker X8 APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.960, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26304, 5715, 4227 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.135, 1.06 |
No. of reflections | 5715 |
No. of parameters | 238 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.36 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.86 (1) | 2.19 (1) | 2.986 (2) | 154 (2) |
Symmetry code: (i) −x+3/2, y+1/2, −z+3/2. |
Acknowledgements
We thank the Université Mohammed V-Agdal and the University of Malaya for supporting this study.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bouhfid, R., Joly, N., Ohmani, F., Essassi, E. M., Massoui, M. & Martin, P. (2008). Lett. Org. Chem. pp. 3–7. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar
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N-Substituted isatins (Bouhfid et al., 2008) represent a large family of heterocyclic compounds reported to show a wide range of useful medicinal properties. These condense readily with thiosemicarbazides to form crystalline thiosemicarbazones. The title 1-decylisatin derivative has a Z configuration around the imine C=N bond and E configuration the C(=S)–NH2 bond (Scheme I, Fig. 1). The molecules form zigzag chains though N–H···O hydrogen bonds along the b-axis of the monoclinic unit cell (Fig. 2). The decyl chain adopts an irregular zigzag conformation; the irregular nature lead to a compact packing and there are no voids in the crystal.