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

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ISSN: 2056-9890

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

(Received 4 May 2010; accepted 5 May 2010; online 15 May 2010)

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[Bouhfid, R., Joly, N., Ohmani, F., Essassi, E. M., Massoui, M. & Martin, P. (2008). Lett. Org. Chem. pp. 3-7.]).

[Scheme 1]

Experimental

Crystal data
  • C19H28N4OS

  • Mr = 360.51

  • Monoclinic, P 21 /n

  • a = 11.8856 (2) Å

  • b = 11.0055 (2) Å

  • c = 15.1638 (3) Å

  • β = 99.468 (1)°

  • V = 1956.51 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 180 K

  • 0.23 × 0.14 × 0.12 mm

Data collection
  • Bruker X8 APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.960, Tmax = 0.979

  • 26304 measured reflections

  • 5715 independent reflections

  • 4227 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.135

  • S = 1.06

  • 5715 reflections

  • 238 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H11⋯O1i 0.86 (1) 2.19 (1) 2.986 (2) 154 (2)
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).

Supporting information


Comment top

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.

Related literature top

For background to N-substituted isatins and their derivatives, see: Bouhfid et al. (2008).

Experimental top

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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement 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.

Structure description top

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.

For background to N-substituted isatins and their derivatives, see: Bouhfid et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the molecule of C19H28N4OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Packinig diagram of the title compound with hydrogen bonds drawn as dashed lines.
1-(1-Decyl-2-oxoindolin-3-ylidene)thiosemicarbazide top
Crystal data top
C19H28N4OSF(000) = 776
Mr = 360.51Dx = 1.224 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5658 reflections
a = 11.8856 (2) Åθ = 2.3–28.7°
b = 11.0055 (2) ŵ = 0.18 mm1
c = 15.1638 (3) ÅT = 180 K
β = 99.468 (1)°Prism, yellow
V = 1956.51 (6) Å30.23 × 0.14 × 0.12 mm
Z = 4
Data collection top
Bruker X8 APEXII
diffractometer
5715 independent reflections
Radiation source: fine-focus sealed tube4227 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.960, Tmax = 0.979k = 1315
26304 measured reflectionsl = 1821
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H 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 parametersΔρmax = 0.30 e Å3
3 restraintsΔρmin = 0.36 e Å3
Crystal data top
C19H28N4OSV = 1956.51 (6) Å3
Mr = 360.51Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.8856 (2) ŵ = 0.18 mm1
b = 11.0055 (2) ÅT = 180 K
c = 15.1638 (3) Å0.23 × 0.14 × 0.12 mm
β = 99.468 (1)°
Data collection top
Bruker X8 APEXII
diffractometer
5715 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4227 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.979Rint = 0.043
26304 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0423 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.30 e Å3
5715 reflectionsΔρmin = 0.36 e Å3
238 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.80459 (3)0.78130 (4)0.66953 (3)0.03232 (12)
O10.66844 (10)0.67702 (9)0.91795 (7)0.0330 (3)
N10.78312 (11)1.00870 (12)0.72565 (9)0.0304 (3)
N20.73941 (11)0.85612 (11)0.81634 (8)0.0277 (3)
N30.71786 (10)0.93926 (10)0.87721 (8)0.0241 (2)
N40.61721 (10)0.76378 (10)1.04405 (8)0.0232 (2)
C10.77480 (11)0.89065 (12)0.73872 (9)0.0240 (3)
C20.68081 (11)0.89632 (12)0.94641 (9)0.0221 (3)
C30.65089 (11)0.96609 (12)1.02047 (9)0.0214 (3)
C40.65109 (12)1.08920 (12)1.03890 (10)0.0250 (3)
H40.67611.14650.99940.030*
C50.61370 (12)1.12684 (13)1.11687 (10)0.0289 (3)
H50.61361.21091.13100.035*
C60.57670 (12)1.04303 (14)1.17397 (10)0.0296 (3)
H60.55181.07101.22680.035*
C70.57503 (12)0.91890 (13)1.15612 (9)0.0266 (3)
H70.54910.86181.19530.032*
C80.61282 (11)0.88257 (11)1.07871 (9)0.0214 (3)
C90.65662 (12)0.76577 (12)0.96510 (9)0.0240 (3)
C100.58378 (12)0.65187 (12)1.08470 (10)0.0258 (3)
H10A0.54520.59741.03720.031*
H10B0.52860.67161.12490.031*
C110.68480 (13)0.58614 (14)1.13747 (11)0.0329 (3)
H11A0.72320.64041.18520.040*
H11B0.74020.56671.09740.040*
C120.64970 (14)0.46857 (13)1.17964 (11)0.0319 (3)
H12A0.59310.42571.13520.038*
H12B0.71750.41541.19350.038*
C130.59920 (13)0.48675 (12)1.26434 (11)0.0305 (3)
H13A0.52860.53551.25000.037*
H13B0.65390.53341.30790.037*
C140.57148 (13)0.36767 (13)1.30730 (11)0.0314 (3)
H14A0.64070.31611.31680.038*
H14B0.51210.32431.26550.038*
C150.52981 (13)0.38398 (14)1.39615 (11)0.0321 (3)
H15A0.58760.43081.43690.039*
H15B0.45880.43261.38600.039*
C160.50680 (14)0.26574 (14)1.44180 (11)0.0341 (3)
H16A0.57920.22041.45770.041*
H16B0.45400.21531.39960.041*
C170.45517 (16)0.28689 (16)1.52591 (13)0.0431 (4)
H17A0.38890.34201.51110.052*
H17B0.51230.32861.57060.052*
C180.41613 (17)0.17156 (19)1.56828 (14)0.0511 (5)
H18A0.37040.19471.61460.061*
H18B0.36630.12421.52190.061*
C190.5135 (2)0.09282 (19)1.60994 (14)0.0567 (5)
H19A0.48360.02081.63630.085*
H19B0.56250.13861.65670.085*
H19C0.55790.06761.56410.085*
H110.8010 (16)1.0349 (19)0.6760 (9)0.048 (6)*
H120.7606 (16)1.0593 (15)0.7628 (11)0.044 (5)*
H20.7284 (16)0.7811 (10)0.8277 (13)0.044 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0421 (2)0.0309 (2)0.0277 (2)0.00066 (15)0.01700 (16)0.00417 (15)
O10.0523 (7)0.0207 (5)0.0300 (6)0.0001 (4)0.0186 (5)0.0034 (4)
N10.0425 (7)0.0262 (6)0.0262 (6)0.0024 (5)0.0164 (6)0.0043 (5)
N20.0427 (7)0.0197 (5)0.0247 (6)0.0004 (5)0.0175 (5)0.0007 (5)
N30.0297 (6)0.0216 (5)0.0227 (6)0.0011 (4)0.0095 (5)0.0007 (4)
N40.0316 (6)0.0180 (5)0.0222 (6)0.0008 (4)0.0106 (5)0.0025 (4)
C10.0247 (6)0.0266 (6)0.0216 (6)0.0011 (5)0.0069 (5)0.0015 (5)
C20.0268 (6)0.0193 (6)0.0214 (6)0.0013 (5)0.0074 (5)0.0007 (5)
C30.0242 (6)0.0199 (6)0.0207 (6)0.0006 (5)0.0052 (5)0.0003 (5)
C40.0287 (7)0.0208 (6)0.0262 (7)0.0004 (5)0.0062 (5)0.0009 (5)
C50.0350 (7)0.0226 (6)0.0293 (8)0.0010 (5)0.0064 (6)0.0063 (5)
C60.0346 (8)0.0320 (7)0.0233 (7)0.0021 (6)0.0081 (6)0.0056 (6)
C70.0323 (7)0.0281 (7)0.0209 (7)0.0007 (5)0.0087 (5)0.0007 (5)
C80.0246 (6)0.0198 (6)0.0202 (6)0.0020 (5)0.0048 (5)0.0005 (5)
C90.0306 (7)0.0204 (6)0.0226 (6)0.0006 (5)0.0091 (5)0.0015 (5)
C100.0313 (7)0.0202 (6)0.0274 (7)0.0029 (5)0.0095 (6)0.0035 (5)
C110.0336 (7)0.0268 (7)0.0400 (9)0.0001 (6)0.0107 (6)0.0105 (6)
C120.0383 (8)0.0219 (6)0.0370 (8)0.0034 (6)0.0104 (7)0.0079 (6)
C130.0341 (7)0.0207 (6)0.0373 (8)0.0011 (5)0.0077 (6)0.0058 (6)
C140.0350 (8)0.0240 (7)0.0361 (8)0.0001 (6)0.0082 (6)0.0077 (6)
C150.0345 (8)0.0281 (7)0.0345 (8)0.0001 (6)0.0076 (6)0.0064 (6)
C160.0367 (8)0.0304 (7)0.0366 (9)0.0013 (6)0.0102 (7)0.0080 (6)
C170.0451 (9)0.0427 (10)0.0453 (10)0.0034 (7)0.0186 (8)0.0095 (8)
C180.0539 (11)0.0584 (12)0.0445 (11)0.0115 (9)0.0185 (9)0.0095 (9)
C190.0836 (15)0.0492 (11)0.0392 (10)0.0012 (10)0.0159 (10)0.0104 (9)
Geometric parameters (Å, º) top
S1—C11.6723 (14)C11—C121.531 (2)
O1—C91.2320 (17)C11—H11A0.9900
N1—C11.3204 (18)C11—H11B0.9900
N1—H110.864 (9)C12—C131.518 (2)
N1—H120.865 (9)C12—H12A0.9900
N2—N31.3537 (16)C12—H12B0.9900
N2—C11.3673 (17)C13—C141.5235 (19)
N2—H20.858 (9)C13—H13A0.9900
N3—C21.2924 (17)C13—H13B0.9900
N4—C91.3556 (17)C14—C151.521 (2)
N4—C81.4132 (16)C14—H14A0.9900
N4—C101.4613 (17)C14—H14B0.9900
C2—C31.4521 (18)C15—C161.520 (2)
C2—C91.5014 (18)C15—H15A0.9900
C3—C41.3833 (18)C15—H15B0.9900
C3—C81.4004 (18)C16—C171.521 (2)
C4—C51.3928 (19)C16—H16A0.9900
C4—H40.9500C16—H16B0.9900
C5—C61.385 (2)C17—C181.529 (3)
C5—H50.9500C17—H17A0.9900
C6—C71.392 (2)C17—H17B0.9900
C6—H60.9500C18—C191.499 (3)
C7—C81.3831 (18)C18—H18A0.9900
C7—H70.9500C18—H18B0.9900
C10—C111.513 (2)C19—H19A0.9800
C10—H10A0.9900C19—H19B0.9800
C10—H10B0.9900C19—H19C0.9800
C1—N1—H11119.6 (15)C13—C12—C11114.51 (13)
C1—N1—H12119.8 (13)C13—C12—H12A108.6
H11—N1—H12119.9 (19)C11—C12—H12A108.6
N3—N2—C1121.24 (12)C13—C12—H12B108.6
N3—N2—H2117.5 (13)C11—C12—H12B108.6
C1—N2—H2121.3 (13)H12A—C12—H12B107.6
C2—N3—N2115.75 (11)C12—C13—C14113.07 (12)
C9—N4—C8110.65 (11)C12—C13—H13A109.0
C9—N4—C10122.93 (11)C14—C13—H13A109.0
C8—N4—C10126.41 (11)C12—C13—H13B109.0
N1—C1—N2116.36 (12)C14—C13—H13B109.0
N1—C1—S1125.81 (11)H13A—C13—H13B107.8
N2—C1—S1117.83 (10)C13—C14—C15113.72 (13)
N3—C2—C3126.45 (12)C13—C14—H14A108.8
N3—C2—C9127.20 (12)C15—C14—H14A108.8
C3—C2—C9106.33 (11)C13—C14—H14B108.8
C4—C3—C8120.36 (12)C15—C14—H14B108.8
C4—C3—C2132.97 (12)H14A—C14—H14B107.7
C8—C3—C2106.64 (11)C16—C15—C14114.32 (13)
C3—C4—C5118.21 (13)C16—C15—H15A108.7
C3—C4—H4120.9C14—C15—H15A108.7
C5—C4—H4120.9C16—C15—H15B108.7
C6—C5—C4120.72 (13)C14—C15—H15B108.7
C6—C5—H5119.6H15A—C15—H15B107.6
C4—C5—H5119.6C15—C16—C17112.24 (14)
C5—C6—C7121.85 (13)C15—C16—H16A109.2
C5—C6—H6119.1C17—C16—H16A109.2
C7—C6—H6119.1C15—C16—H16B109.2
C8—C7—C6116.91 (13)C17—C16—H16B109.2
C8—C7—H7121.5H16A—C16—H16B107.9
C6—C7—H7121.5C16—C17—C18114.67 (16)
C7—C8—C3121.95 (12)C16—C17—H17A108.6
C7—C8—N4128.32 (12)C18—C17—H17A108.6
C3—C8—N4109.70 (11)C16—C17—H17B108.6
O1—C9—N4126.06 (12)C18—C17—H17B108.6
O1—C9—C2127.26 (12)H17A—C17—H17B107.6
N4—C9—C2106.67 (11)C19—C18—C17112.98 (16)
N4—C10—C11112.26 (12)C19—C18—H18A109.0
N4—C10—H10A109.2C17—C18—H18A109.0
C11—C10—H10A109.2C19—C18—H18B109.0
N4—C10—H10B109.2C17—C18—H18B109.0
C11—C10—H10B109.2H18A—C18—H18B107.8
H10A—C10—H10B107.9C18—C19—H19A109.5
C10—C11—C12112.20 (12)C18—C19—H19B109.5
C10—C11—H11A109.2H19A—C19—H19B109.5
C12—C11—H11A109.2C18—C19—H19C109.5
C10—C11—H11B109.2H19A—C19—H19C109.5
C12—C11—H11B109.2H19B—C19—H19C109.5
H11A—C11—H11B107.9
C1—N2—N3—C2177.49 (13)C10—N4—C8—C71.2 (2)
N3—N2—C1—N12.0 (2)C9—N4—C8—C30.06 (16)
N3—N2—C1—S1177.49 (10)C10—N4—C8—C3179.47 (12)
N2—N3—C2—C3179.58 (13)C8—N4—C9—O1178.82 (14)
N2—N3—C2—C91.7 (2)C10—N4—C9—O10.6 (2)
N3—C2—C3—C40.7 (2)C8—N4—C9—C20.34 (15)
C9—C2—C3—C4177.54 (15)C10—N4—C9—C2179.77 (12)
N3—C2—C3—C8178.72 (13)N3—C2—C9—O10.4 (2)
C9—C2—C3—C80.44 (14)C3—C2—C9—O1178.66 (14)
C8—C3—C4—C50.6 (2)N3—C2—C9—N4178.74 (13)
C2—C3—C4—C5178.39 (14)C3—C2—C9—N40.48 (15)
C3—C4—C5—C60.4 (2)C9—N4—C10—C1183.30 (17)
C4—C5—C6—C70.1 (2)C8—N4—C10—C1197.36 (16)
C5—C6—C7—C80.4 (2)N4—C10—C11—C12179.72 (12)
C6—C7—C8—C30.2 (2)C10—C11—C12—C1378.90 (18)
C6—C7—C8—N4178.24 (14)C11—C12—C13—C14176.76 (13)
C4—C3—C8—C70.4 (2)C12—C13—C14—C15175.33 (13)
C2—C3—C8—C7178.65 (12)C13—C14—C15—C16177.44 (13)
C4—C3—C8—N4178.04 (12)C14—C15—C16—C17174.78 (14)
C2—C3—C8—N40.25 (15)C15—C16—C17—C18172.62 (15)
C9—N4—C8—C7178.21 (14)C16—C17—C18—C1969.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H12···S1i0.87 (1)2.81 (1)3.628 (1)159 (2)
N1—H11···O1i0.86 (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 formulaC19H28N4OS
Mr360.51
Crystal system, space groupMonoclinic, P21/n
Temperature (K)180
a, b, c (Å)11.8856 (2), 11.0055 (2), 15.1638 (3)
β (°) 99.468 (1)
V3)1956.51 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.23 × 0.14 × 0.12
Data collection
DiffractometerBruker X8 APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.960, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
26304, 5715, 4227
Rint0.043
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.135, 1.06
No. of reflections5715
No. of parameters238
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.86 (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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBouhfid, R., Joly, N., Ohmani, F., Essassi, E. M., Massoui, M. & Martin, P. (2008). Lett. Org. Chem. pp. 3–7.  Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.  Google Scholar

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