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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 1| January 2015| Pages o35-o36
https://doi.org/10.1107/S2056989014026395

Crystal structure of (E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethyl­­idene]-N-methyl­hydrazine-1-carbo­thio­amide

Adriano Bof de Oliveira,a* Christian Näther,b Inke Jess,b Renan Lira de Fariasa and Iasmin Alves Ribeiroa

aDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, 49100-000 São Cristóvão-SE, Brazil, and bInstitut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth Strasse 2, D-24118 Kiel, Germany
*Correspondence e-mail: adriano@daad-alumni.de

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 28 November 2014; accepted 1 December 2014; online 1 January 2015)

In the title compound, C11H13N3O2S, there is a short intra­molecular N—H⋯N contact. The benzo[d][1,3]dioxole ring system is approximately planar (r.m.s. deviation = 0.025 Å) and makes a dihedral angle of 56.83 (6)° with the mean plane of the methyl­thio­semicarbazone fragment [–N—N—C(=S)—N—C; maximum deviation = 0.1111 (14) Å for the imino N atom]. In the crystal, mol­ecules are linked via pairs of N—H⋯S hydrogen bonds, forming inversion dimers. The dimers are connected by N—H⋯S hydrogen bonds into layers parallel to (100). The H atoms of both methyl groups are disordered over two sets of sites and were refined with occupancy ratios of 0.5:0.5 and 0.75:0.25.

CCDC reference: 1036961

Similar articles

1. Related literature

For one of the first reports of the synthesis of thio­semicarbazone derivatives, see: Freund & Schander (1902[Freund, M. & Schander, A. (1902). Ber. Dtsch. Chem. Ges. 35, 2602-2606.]). For one of the first reports of 3,4-methyl­ene­dioxy­aceto­phenone and its extraction from the South American rosewood tree, see: Mors et al. (1957[Mors, W. B., Gottlieb, O. R. & Djerassi, C. (1957). J. Am. Chem. Soc. 79, 4507-4511.]). For the crystal structure of a derivative of the title compound, 1-(2H-1,3-benzodioxol-5-yl)ethanone thio­semicarbazone, see: Oliveira et al. (2013[Oliveira, A. B. de, Farias, R. L. de, Näther, C., Jess, I. & Bresolin, L. (2013). Acta Cryst. E69, o644.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C11H13N3O2S

  • Mr = 251.30

  • Monoclinic, P 21 /c

  • a = 8.7927 (4) Å

  • b = 12.5979 (6) Å

  • c = 10.9254 (4) Å

  • β = 106.098 (3)°

  • V = 1162.75 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 200 K

  • 0.2 × 0.1 × 0.1 mm

2.2. Data collection

  • Stoe IPDS-1 diffractometer

  • 12631 measured reflections

  • 2530 independent reflections

  • 2166 reflections with I > 2σ(I)

  • Rint = 0.034

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.096

  • S = 1.06

  • 2530 reflections

  • 157 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H1N3⋯N1 0.88 2.17 2.6080 (19) 110
N2—H1N2⋯S1i 0.88 2.62 3.4871 (14) 168
N3—H1N3⋯S1ii 0.88 2.86 3.4973 (14) 131
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA and X-RED32. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA and X-RED32. Stoe & Cie GmbH, Darmstadt, Germany.]); 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1036961

Crystal structure: contains datablocks I, publication_text. DOI: https://doi.org/10.1107/S2056989014026395/su5032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026395/su5032Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014026395/su5032Isup3.cml

checkCIF report


Structural commentary top

In our research we are inter­ested in the synthesis of thio­semicarbazone derivatives of natural products. Herein, we report the synthesis and crystal structure of 1-(2H-1,3-benzodioxol-5-yl)ethanone 4-methyl­thio­semicarbazone, a product of the reaction between 3',4'-(methyl­ene­dioxy)­aceto­phenone and 4-methyl­thio­semicarbazide. The ketone is a natural product obtained from the South American rosewood trees that belong to the Lauraceae family (Mors et al., 1957).

In the title molecule, Fig. 1, the torsion angle for the N1–N2–C10–N3 entity is 10.2 (2)°. The maximum deviation from the mean plane of the non-H atoms for the C1—C9/O1—O2 fragment and for the C10—C11/N1—N3/S1 fragment amount to 0.2844 (14) Å and 0.1111 (12) Å, respectively, and the angle between their mean planes is 55.39 (4) °. The molecule has two disordered methyl groups. The H atoms of the terminal methyl substituent, C11, are disordered over two sets of sites with an occupancy ratio of 0.75:0.25, those of the other methyl substituent, C9, attached to the Schiff base are disordered over two sets of sites with an occupancy ratio of 0.5:0.5 (Fig. 1).

In the crystal, the molecules are linked via pairs of N2—H1N2···S1 hydrogen bonds into inversion dimers. These dimers are connected by weak N3—H1N3···S1 hydrogen bonds into layers, that are parallel to the bc plane. Finally, an intra­molecular N3—H1N3···N1 hydrogen bond is also observed (Figs. 2 and 3, and Table 1).

Synthesis and crystallization top

The synthesis of the title compound was adapted from a previously reported procedure (Freund & Schander, 1902). In a hydro­chloric acid catalyzed reaction, a mixture of 3',4'-(methyl­ene­dioxy)­aceto­phenone (10 mmol) and 4-Methyl-3-thio­semicarbazide (10 mmol) in ethanol (80 ml) was refluxed for 6 h. After cooling and filtering, the title compound was obtained. Colourless crystals were obtained in DMSO by the slow evaporation of the solvent.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The NH H atoms were located in a difference Fourier map and were refined as riding atoms with N—H = 0.88 Å and with Uiso(H) = 1.5Ueq(N). The C-bound H atoms were positioned with idealized geometry and refined as riding atoms: C—H = 0.95 - 0.99 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms. The H atoms of methyl groups, C9 and C11, are disordered over two positions and were refined in two different orientations rotated by 60° with occupancy ratios of 0.5:0.5 and 0.75:0.25, respectively.

Related literature top

For one of the first reports of the synthesis of thiosemicarbazone derivatives, see: Freund & Schander (1902). For one of the first reports of 3,4-methylenedioxyacetophenone and its extraction from the South American rosewood tree, see: Mors et al. (1957). For the crystal structure of a derivative of the title compound, 1-(2H-1,3-benzodioxol-5-yl)ethanone thiosemicarbazone, see: Oliveira et al. (2013).

Structure description top

In our research we are inter­ested in the synthesis of thio­semicarbazone derivatives of natural products. Herein, we report the synthesis and crystal structure of 1-(2H-1,3-benzodioxol-5-yl)ethanone 4-methyl­thio­semicarbazone, a product of the reaction between 3',4'-(methyl­ene­dioxy)­aceto­phenone and 4-methyl­thio­semicarbazide. The ketone is a natural product obtained from the South American rosewood trees that belong to the Lauraceae family (Mors et al., 1957).

In the title molecule, Fig. 1, the torsion angle for the N1–N2–C10–N3 entity is 10.2 (2)°. The maximum deviation from the mean plane of the non-H atoms for the C1—C9/O1—O2 fragment and for the C10—C11/N1—N3/S1 fragment amount to 0.2844 (14) Å and 0.1111 (12) Å, respectively, and the angle between their mean planes is 55.39 (4) °. The molecule has two disordered methyl groups. The H atoms of the terminal methyl substituent, C11, are disordered over two sets of sites with an occupancy ratio of 0.75:0.25, those of the other methyl substituent, C9, attached to the Schiff base are disordered over two sets of sites with an occupancy ratio of 0.5:0.5 (Fig. 1).

In the crystal, the molecules are linked via pairs of N2—H1N2···S1 hydrogen bonds into inversion dimers. These dimers are connected by weak N3—H1N3···S1 hydrogen bonds into layers, that are parallel to the bc plane. Finally, an intra­molecular N3—H1N3···N1 hydrogen bond is also observed (Figs. 2 and 3, and Table 1).

For one of the first reports of the synthesis of thiosemicarbazone derivatives, see: Freund & Schander (1902). For one of the first reports of 3,4-methylenedioxyacetophenone and its extraction from the South American rosewood tree, see: Mors et al. (1957). For the crystal structure of a derivative of the title compound, 1-(2H-1,3-benzodioxol-5-yl)ethanone thiosemicarbazone, see: Oliveira et al. (2013).

Synthesis and crystallization top

The synthesis of the title compound was adapted from a previously reported procedure (Freund & Schander, 1902). In a hydro­chloric acid catalyzed reaction, a mixture of 3',4'-(methyl­ene­dioxy)­aceto­phenone (10 mmol) and 4-Methyl-3-thio­semicarbazide (10 mmol) in ethanol (80 ml) was refluxed for 6 h. After cooling and filtering, the title compound was obtained. Colourless crystals were obtained in DMSO by the slow evaporation of the solvent.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The NH H atoms were located in a difference Fourier map and were refined as riding atoms with N—H = 0.88 Å and with Uiso(H) = 1.5Ueq(N). The C-bound H atoms were positioned with idealized geometry and refined as riding atoms: C—H = 0.95 - 0.99 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms. The H atoms of methyl groups, C9 and C11, are disordered over two positions and were refined in two different orientations rotated by 60° with occupancy ratios of 0.5:0.5 and 0.75:0.25, respectively.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-RED32 (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labelling. Displacement ellipsoids are drawn at the 40% probability level. Disordered H atoms are shown with white and light gray interior colours and the short intramolecular N-H···N contact is shown as a dashed line (see Table 1 for details).
[Figure 2] Fig. 2. A view of the intramolecular and intermolecular hydrogen bonds (dashed lines) in the crystal structure of the title compound (see Table 1 for details of the hydrogen bonding and the symmetry codes; disordered H atoms are not shown for clarity).
[Figure 3] Fig. 3. A partial view along the c axis of the crystal packing of the title compound. The N2—H1N2···S1 hydrogen bonds are shown as dashed lines (see Table 1 for details; disordered H atoms are not shown for clarity).
(E)-2-[1-(Benzo[d][1,3]dioxol-5-yl)ethylidene]-N-methylhydrazine-1-carbothioamide top
Crystal data top
C11H13N3O2SZ = 4
Mr = 251.30F(000) = 528
Monoclinic, P21/cDx = 1.436 Mg m−3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.7927 (4) Åθ = 2.4–27.0°
b = 12.5979 (6) ŵ = 0.27 mm−1
c = 10.9254 (4) ÅT = 200 K
β = 106.098 (3)°Prism, colourless
V = 1162.75 (9) Å30.2 × 0.1 × 0.1 mm
Data collection top
Stoe IPDS-1
diffractometer		2166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Stoe IPDS-1Rint = 0.034
Graphite monochromatorθmax = 27.0°, θmin = 2.4°
φ scansh = −11→11
12631 measured reflectionsk = −16→16
2530 independent reflectionsl = −13→13
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0452P)2 + 0.3583P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2530 reflectionsΔρmax = 0.22 e Å−3
157 parametersΔρmin = −0.21 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (3)
Crystal data top
C11H13N3O2SV = 1162.75 (9) Å3
Mr = 251.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.7927 (4) ŵ = 0.27 mm−1
b = 12.5979 (6) ÅT = 200 K
c = 10.9254 (4) Å0.2 × 0.1 × 0.1 mm
β = 106.098 (3)°
Data collection top
Stoe IPDS-1
diffractometer		2166 reflections with I > 2σ(I)
12631 measured reflectionsRint = 0.034
2530 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.06Δρmax = 0.22 e Å−3
2530 reflectionsΔρmin = −0.21 e Å−3
157 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.79760 (18)0.61024 (12)0.64282 (15)0.0335 (3)
C20.67988 (19)0.60308 (14)0.52567 (16)0.0376 (4)
H20.57180.59290.52240.045*
C30.72677 (19)0.61135 (13)0.41723 (15)0.0363 (4)
C40.8828 (2)0.62849 (14)0.41992 (16)0.0389 (4)
C50.9996 (2)0.63636 (16)0.53155 (17)0.0459 (4)
H51.10660.64880.53290.055*
C60.9547 (2)0.62527 (14)0.64410 (17)0.0396 (4)
H61.03370.62810.72350.048*
O10.63513 (15)0.60420 (12)0.29353 (11)0.0499 (3)
C70.7408 (2)0.61449 (15)0.21584 (17)0.0429 (4)
H7A0.70700.67390.15510.052*
H7B0.74070.54850.16660.052*
O20.89564 (15)0.63434 (12)0.29772 (12)0.0513 (4)
C80.75138 (18)0.60240 (12)0.76304 (15)0.0335 (3)
N10.60559 (16)0.62379 (11)0.75398 (13)0.0359 (3)
N20.55651 (16)0.61080 (11)0.86408 (13)0.0368 (3)
H1N20.58280.55350.91130.055*
C90.8720 (2)0.57270 (15)0.88417 (17)0.0433 (4)
H9A0.84000.60090.95680.065*0.50
H9B0.97500.60250.88430.065*0.50
H9C0.88020.49520.89070.065*0.50
H9D0.95680.53150.86440.065*0.50
H9E0.82180.52990.93700.065*0.50
H9F0.91660.63720.93050.065*0.50
C100.42636 (18)0.66446 (12)0.87292 (15)0.0328 (3)
N30.37103 (17)0.73745 (11)0.78479 (14)0.0407 (3)
H1N30.42120.74320.72570.061*
S10.34744 (5)0.63743 (3)0.99435 (4)0.03782 (15)
C110.2532 (2)0.81607 (15)0.79064 (19)0.0491 (5)
H11A0.26360.87770.73870.074*0.25
H11B0.26900.83840.87920.074*0.25
H11C0.14730.78540.75790.074*0.25
H11D0.18960.79000.84520.074*0.75
H11E0.18420.82920.70470.074*0.75
H11F0.30590.88230.82600.074*0.75
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0351 (8)0.0332 (8)0.0342 (8)0.0027 (6)0.0129 (6)0.0018 (6)
C20.0319 (8)0.0451 (9)0.0384 (9)0.0008 (6)0.0142 (7)0.0023 (7)
C30.0353 (8)0.0395 (8)0.0343 (8)0.0004 (6)0.0098 (6)−0.0001 (6)
C40.0409 (9)0.0447 (9)0.0355 (8)−0.0020 (7)0.0179 (7)0.0002 (7)
C50.0339 (8)0.0634 (12)0.0439 (10)−0.0059 (8)0.0164 (7)−0.0005 (8)
C60.0346 (8)0.0483 (9)0.0369 (9)−0.0010 (7)0.0114 (7)0.0003 (7)
O10.0403 (7)0.0789 (9)0.0314 (6)−0.0050 (6)0.0111 (5)−0.0002 (6)
C70.0473 (10)0.0492 (10)0.0354 (9)−0.0048 (8)0.0167 (7)−0.0046 (7)
O20.0435 (7)0.0788 (10)0.0360 (7)−0.0057 (6)0.0182 (6)0.0010 (6)
C80.0354 (8)0.0328 (7)0.0343 (8)0.0018 (6)0.0129 (6)0.0027 (6)
N10.0384 (7)0.0407 (7)0.0326 (7)0.0052 (6)0.0165 (6)0.0050 (5)
N20.0391 (7)0.0416 (7)0.0334 (7)0.0071 (6)0.0164 (6)0.0084 (6)
C90.0388 (9)0.0531 (10)0.0379 (9)0.0000 (7)0.0101 (7)0.0081 (7)
C100.0328 (7)0.0335 (7)0.0327 (8)−0.0019 (6)0.0102 (6)−0.0010 (6)
N30.0420 (8)0.0443 (8)0.0426 (8)0.0101 (6)0.0229 (6)0.0111 (6)
S10.0437 (2)0.0414 (2)0.0333 (2)0.00154 (17)0.01874 (17)0.00216 (16)
C110.0513 (10)0.0473 (10)0.0551 (11)0.0162 (8)0.0255 (9)0.0119 (8)
Geometric parameters (Å, º) top
C1—C61.390 (2)N2—C101.355 (2)
C1—C21.408 (2)N2—H1N20.8800
C1—C81.482 (2)C9—H9A0.9800
C2—C31.362 (2)C9—H9B0.9800
C2—H20.9500C9—H9C0.9800
C3—O11.371 (2)C9—H9D0.9800
C3—C41.381 (2)C9—H9E0.9800
C4—C51.362 (3)C9—H9F0.9800
C4—O21.372 (2)C10—N31.323 (2)
C5—C61.399 (2)C10—S11.6935 (16)
C5—H50.9500N3—C111.448 (2)
C6—H60.9500N3—H1N30.8800
O1—C71.427 (2)C11—H11A0.9800
C7—O21.429 (2)C11—H11B0.9800
C7—H7A0.9900C11—H11C0.9800
C7—H7B0.9900C11—H11D0.9800
C8—N11.287 (2)C11—H11E0.9800
C8—C91.496 (2)C11—H11F0.9800
N1—N21.3957 (18)
C6—C1—C2119.71 (15)H9B—C9—H9D56.3
C6—C1—C8121.06 (14)H9C—C9—H9D56.3
C2—C1—C8119.22 (14)C8—C9—H9E109.5
C3—C2—C1117.53 (15)H9A—C9—H9E56.3
C3—C2—H2121.2H9B—C9—H9E141.1
C1—C2—H2121.2H9C—C9—H9E56.3
C2—C3—O1127.99 (15)H9D—C9—H9E109.5
C2—C3—C4122.14 (16)C8—C9—H9F109.5
O1—C3—C4109.88 (15)H9A—C9—H9F56.3
C5—C4—O2128.48 (15)H9B—C9—H9F56.3
C5—C4—C3121.85 (16)H9C—C9—H9F141.1
O2—C4—C3109.67 (15)H9D—C9—H9F109.5
C4—C5—C6116.98 (16)H9E—C9—H9F109.5
C4—C5—H5121.5N3—C10—N2116.24 (14)
C6—C5—H5121.5N3—C10—S1124.21 (12)
C1—C6—C5121.76 (16)N2—C10—S1119.53 (12)
C1—C6—H6119.1C10—N3—C11124.52 (14)
C5—C6—H6119.1C10—N3—H1N3115.7
C3—O1—C7106.19 (13)C11—N3—H1N3119.1
O1—C7—O2107.93 (13)N3—C11—H11A109.5
O1—C7—H7A110.1N3—C11—H11B109.5
O2—C7—H7A110.1H11A—C11—H11B109.5
O1—C7—H7B110.1N3—C11—H11C109.5
O2—C7—H7B110.1H11A—C11—H11C109.5
H7A—C7—H7B108.4H11B—C11—H11C109.5
C4—O2—C7106.18 (13)N3—C11—H11D109.5
N1—C8—C1115.47 (14)H11A—C11—H11D141.1
N1—C8—C9124.57 (15)H11B—C11—H11D56.3
C1—C8—C9119.95 (14)H11C—C11—H11D56.3
C8—N1—N2116.66 (13)N3—C11—H11E109.5
C10—N2—N1118.15 (13)H11A—C11—H11E56.3
C10—N2—H1N2117.2H11B—C11—H11E141.1
N1—N2—H1N2120.5H11C—C11—H11E56.3
C8—C9—H9A109.5H11D—C11—H11E109.5
C8—C9—H9B109.5N3—C11—H11F109.5
H9A—C9—H9B109.5H11A—C11—H11F56.3
C8—C9—H9C109.5H11B—C11—H11F56.3
H9A—C9—H9C109.5H11C—C11—H11F141.1
H9B—C9—H9C109.5H11D—C11—H11F109.5
C8—C9—H9D109.5H11E—C11—H11F109.5
H9A—C9—H9D141.1
C6—C1—C2—C30.0 (2)C5—C4—O2—C7176.38 (19)
C8—C1—C2—C3179.57 (15)C3—C4—O2—C7−2.97 (19)
C1—C2—C3—O1178.21 (16)O1—C7—O2—C43.96 (19)
C1—C2—C3—C4−1.4 (3)C6—C1—C8—N1157.83 (16)
C2—C3—C4—C51.1 (3)C2—C1—C8—N1−21.7 (2)
O1—C3—C4—C5−178.57 (17)C6—C1—C8—C9−21.4 (2)
C2—C3—C4—O2−179.47 (16)C2—C1—C8—C9159.10 (16)
O1—C3—C4—O20.8 (2)N1—C8—N1—N20 (79)
O2—C4—C5—C6−178.68 (17)C1—C8—N1—N2176.24 (13)
C3—C4—C5—C60.6 (3)C9—C8—N1—N2−4.6 (2)
C2—C1—C6—C51.7 (3)C8—N1—N2—C10157.92 (15)
C8—C1—C6—C5−177.83 (16)N1—N2—C10—N3−10.2 (2)
C4—C5—C6—C1−2.0 (3)N1—N2—C10—S1171.13 (11)
C2—C3—O1—C7−178.00 (18)N2—C10—N3—C11−167.92 (17)
C4—C3—O1—C71.7 (2)S1—C10—N3—C1110.7 (3)
C3—O1—C7—O2−3.47 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N3···N10.882.172.6080 (19)110
N2—H1N2···S1i0.882.623.4871 (14)168
N3—H1N3···S1ii0.882.863.4973 (14)131
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N3···N10.882.172.6080 (19)110
N2—H1N2···S1i0.882.623.4871 (14)168
N3—H1N3···S1ii0.882.863.4973 (14)131
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z−1/2.
 

Acknowledgements

We gratefully acknowledge financial support by the State of Schleswig–Holstein, Germany. We thank Professor Dr Wolfgang Bensch for access to his experimental facilities. IAR thanks CINTTEC/FAPITEC/UFS for the award of a PIBITI scholarship.

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 71| Part 1| January 2015| Pages o35-o36
https://doi.org/10.1107/S2056989014026395
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