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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 5| May 2015| Pages o313-o314
https://doi.org/10.1107/S2056989015007227

Crystal structure of 4-hy­dr­oxy-3-meth­­oxy­benzaldehyde 4-methyl­thio­semi­carbazone methanol monosolvate

Adriano Bof de Oliveira,a* Johannes Beck,b Christian Landvogtb and Bárbara Regina Santos Feitosaa

aDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, 49100-000 São Cristóvão-SE, Brazil, and bInstitut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany
*Correspondence e-mail: adriano@daad-alumni.de

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 7 April 2015; accepted 10 April 2015; online 18 April 2015)

In the title solvate, C15H15N3O2S·CH3OH, the thio­semicarbazone mol­ecule is approximately planar; the maximum deviation from the mean plane is 0.4659 (14) Å and the dihedral angle between the aromatic rings is 9.83 (8)°. This conformation is supported by an intra­molecular N—H⋯N hydrogen bond. In the crystal, the thio­semicarbazone mol­ecules are linked into dimers by pairs of N—H⋯S hydrogen bonds, thereby generating R22(8) loops. The methanol solvent mol­ecule bonds to the thio­semicarbazone mol­ecule through a bifurcated O—H⋯(O,O) hydrogen bond and also accepts an O—H⋯O link from the thio­semicarbazone mol­ecule. Together, these links generate a three-dimensional network.

CCDC reference: 1059141

Similar articles

1. Related literature

For one of the first reports of thio­semicarbazone derivatives synthesis, see: Freund & Schander (1902[Freund, M. & Schander, A. (1902). Ber. Dtsch. Chem. Ges. 35, 2602-2606.]). For the report concerning the synthesis and crystal structure of 4-hy­droxy-3-meth­oxy­benzaldehyde 4-phenyl­thio­semicarbazone, see: Oliveira et al. (2014[Oliveira, A. B. de, Feitosa, B. R. S., Näther, C. & Jess, I. (2014). Acta Cryst. E70, o278.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C15H15N3O2S·CH4O

  • Mr = 333.40

  • Monoclinic, P 21 /n

  • a = 11.1833 (2) Å

  • b = 8.4207 (2) Å

  • c = 17.2521 (4) Å

  • β = 95.752 (1)°

  • V = 1616.47 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 123 K

  • 0.29 × 0.15 × 0.09 mm

2.2. Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.924, Tmax = 0.983

  • 46461 measured reflections

  • 3692 independent reflections

  • 2926 reflections with I > 2σ(I)

  • Rint = 0.053

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.091

  • S = 1.05

  • 3692 reflections

  • 284 parameters

  • All H-atom parameters refined

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H13⋯N2 0.866 (18) 2.082 (17) 2.5865 (16) 116.4 (14)
N1—H14⋯S1i 0.896 (19) 2.530 (19) 3.4033 (13) 165.2 (15)
O1—H15⋯O3ii 0.86 (2) 1.81 (2) 2.6562 (14) 167.7 (19)
O3—H19⋯O2 0.83 (2) 2.26 (2) 2.8853 (14) 132.1 (18)
O3—H19⋯O1 0.83 (2) 2.46 (2) 3.1645 (15) 144.2 (18)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press, United States.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press, United States.]) and SCALEPACK; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

CCDC reference: 1059141

Crystal structure: contains datablocks I, publication_text. DOI: https://doi.org/10.1107/S2056989015007227/hb7402sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007227/hb7402Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015007227/hb7402Isup3.cml

checkCIF report


Structural commentary top

Concerning our on-going research on the supra­molecular chemistry of thio­semicarbazone derivatives from natural products, we report herein the synthesis and structure of the 4-hy­droxy-3-meth­oxy­benzaldehyde 4-phenyl­thio­semicarbazone methanol monosolvate, a thio­semicarbazone derivative from vanillin. The thio­semicarbazone group of the title compound doesn't match the ideal planarity and the maximum deviation from the mean plane of the non-H atoms concerning the thio­semicarbazone group amounts to 0.4659 (14) Å for C15 and the dihedral angle between the two aromatic rings amounts to 9.83 (8)° (Fig. 1). In the crystal, molecules are linked into dimers via pairs of N1—H14···S1 hydrogen bonds. The dimers are linked into a three dimensional hydrogen bonded network through the methanol molecules by the O1—H15···O3, O3—H19···O2 and O3—H19···O1 hydrogen inter­actions (Fig. 2). In addition, one inter­molecular N3—H13···N2 hydrogen inter­action is also observed (Table 1).

The crystal structure of the solvate free 4-hy­droxy-3-meth­oxy­benzaldehyde 4-phenyl­thio­semicarbazone is already published (Oliveira et al., 2014) and the molecules are linked by N—H···S hydrogen inter­actions into dimers. Additionally, the dimers are linked by N—H···O and O—H···S hydrogen inter­actions building a three-dimensional hydrogen-bonded network.

In the actual structure, the presence of the methanol solvate molecules maintains the dimensionality of the network. As the outstanding feature, a bifurcated hydrogen bond is observed. The atom H19 of the hy­droxy group of the methanol solvate builds a bifurcated hydrogen bond with the O1 and O2 atoms of the ortho-hy­droxy-meth­oxy entity of the thio­semicarbazone derivative. The H19···O2 and H19···O1 distances amount to 2.26 (2) Å and 2.46 (2) Å (Fig. 1). As the difference between the lengths of the two hydrogen inter­actions is about 0.2 Å, the bifurcation is considered symmetric. Due to the hydrogen-bond inter­actions promoted by the solvate molecule, the supra­molecularity of the structure modifies the arrangement molecules but the three-dimensional H-bonded network is preserved (Fig. 2).

Synthesis and crystallization top

Starting materials were commercially available and were used without further purification. The synthesis of the title compound, 4-hy­droxy-3-meth­oxy­benzaldehyde-4-methyl­thio­semicarbazone, was adapted from a previously procedure (Freund & Schander, 1902 and Oliveira et al., 2014). Colourless blocks were obtained unexpectedly from a mixture containing uranyl acetate dihydrate and the title compound in methanol by the slow evaporation of the solvent.

Refinement top

Crystal data, data collection and structure refinement details are summarized in the Experimental part. All hydrogen atoms were localized in a difference density Fourier map. Their positions and isotropic displacement parameters were refined.

Related literature top

For one of the first reports of thiosemicarbazone derivatives synthesis, see: Freund & Schander (1902). For the report concerning the synthesis and crystal structure of 4-hydroxy-3-methoxybenzaldehyde 4-phenylthiosemicarbazone, see: Oliveira et al. (2014).

Structure description top

Concerning our on-going research on the supra­molecular chemistry of thio­semicarbazone derivatives from natural products, we report herein the synthesis and structure of the 4-hy­droxy-3-meth­oxy­benzaldehyde 4-phenyl­thio­semicarbazone methanol monosolvate, a thio­semicarbazone derivative from vanillin. The thio­semicarbazone group of the title compound doesn't match the ideal planarity and the maximum deviation from the mean plane of the non-H atoms concerning the thio­semicarbazone group amounts to 0.4659 (14) Å for C15 and the dihedral angle between the two aromatic rings amounts to 9.83 (8)° (Fig. 1). In the crystal, molecules are linked into dimers via pairs of N1—H14···S1 hydrogen bonds. The dimers are linked into a three dimensional hydrogen bonded network through the methanol molecules by the O1—H15···O3, O3—H19···O2 and O3—H19···O1 hydrogen inter­actions (Fig. 2). In addition, one inter­molecular N3—H13···N2 hydrogen inter­action is also observed (Table 1).

The crystal structure of the solvate free 4-hy­droxy-3-meth­oxy­benzaldehyde 4-phenyl­thio­semicarbazone is already published (Oliveira et al., 2014) and the molecules are linked by N—H···S hydrogen inter­actions into dimers. Additionally, the dimers are linked by N—H···O and O—H···S hydrogen inter­actions building a three-dimensional hydrogen-bonded network.

In the actual structure, the presence of the methanol solvate molecules maintains the dimensionality of the network. As the outstanding feature, a bifurcated hydrogen bond is observed. The atom H19 of the hy­droxy group of the methanol solvate builds a bifurcated hydrogen bond with the O1 and O2 atoms of the ortho-hy­droxy-meth­oxy entity of the thio­semicarbazone derivative. The H19···O2 and H19···O1 distances amount to 2.26 (2) Å and 2.46 (2) Å (Fig. 1). As the difference between the lengths of the two hydrogen inter­actions is about 0.2 Å, the bifurcation is considered symmetric. Due to the hydrogen-bond inter­actions promoted by the solvate molecule, the supra­molecularity of the structure modifies the arrangement molecules but the three-dimensional H-bonded network is preserved (Fig. 2).

For one of the first reports of thiosemicarbazone derivatives synthesis, see: Freund & Schander (1902). For the report concerning the synthesis and crystal structure of 4-hydroxy-3-methoxybenzaldehyde 4-phenylthiosemicarbazone, see: Oliveira et al. (2014).

Synthesis and crystallization top

Starting materials were commercially available and were used without further purification. The synthesis of the title compound, 4-hy­droxy-3-meth­oxy­benzaldehyde-4-methyl­thio­semicarbazone, was adapted from a previously procedure (Freund & Schander, 1902 and Oliveira et al., 2014). Colourless blocks were obtained unexpectedly from a mixture containing uranyl acetate dihydrate and the title compound in methanol by the slow evaporation of the solvent.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in the Experimental part. All hydrogen atoms were localized in a difference density Fourier map. Their positions and isotropic displacement parameters were refined.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. : The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are drawn isotropically. The bifurcated hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. : View of the hydrogen bonding in the structure of the title compound showing the three dimensional H-bonded network. Hydrogen bonding is shown as dashed lines.
4-Hydroxy-3-methoxybenzaldehyde 4-methylthiosemicarbazone methanol monosolvate top
Crystal data top
C15H15N3O2S·CH4OF(000) = 704
Mr = 333.40Dx = 1.370 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 32712 reflections
a = 11.1833 (2) Åθ = 2.9–27.5°
b = 8.4207 (2) ŵ = 0.22 mm−1
c = 17.2521 (4) ÅT = 123 K
β = 95.752 (1)°Block, colorless
V = 1616.47 (6) Å30.29 × 0.15 × 0.09 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer		3692 independent reflections
Radiation source: fine-focus sealed tube, Nonius KappaCCD2926 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.0°
CCD rotation images, thick slices scansh = −14→14
Absorption correction: multi-scan
(Blessing, 1995)		k = −10→10
Tmin = 0.924, Tmax = 0.983l = −22→22
46461 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.091All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.4527P]
where P = (Fo2 + 2Fc2)/3
3692 reflections(Δ/σ)max < 0.001
284 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C15H15N3O2S·CH4OV = 1616.47 (6) Å3
Mr = 333.40Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.1833 (2) ŵ = 0.22 mm−1
b = 8.4207 (2) ÅT = 123 K
c = 17.2521 (4) Å0.29 × 0.15 × 0.09 mm
β = 95.752 (1)°
Data collection top
Nonius KappaCCD
diffractometer		3692 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)		2926 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.983Rint = 0.053
46461 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.091All H-atom parameters refined
S = 1.05Δρmax = 0.21 e Å−3
3692 reflectionsΔρmin = −0.32 e Å−3
284 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*/Ueq
S10.61038 (3)0.16794 (5)0.57257 (2)0.03151 (12)
O1−0.20192 (9)0.56394 (12)0.31751 (6)0.0250 (2)
O2−0.03515 (8)0.71233 (11)0.40440 (6)0.0228 (2)
O3−0.17481 (9)0.93717 (13)0.30693 (6)0.0267 (2)
N10.39757 (10)0.21003 (14)0.49762 (7)0.0211 (2)
N20.29562 (10)0.29685 (13)0.47526 (7)0.0200 (2)
N30.44949 (11)0.40722 (14)0.58388 (7)0.0239 (3)
C10.48140 (12)0.26955 (16)0.55234 (8)0.0207 (3)
C20.21931 (12)0.23390 (16)0.42367 (8)0.0203 (3)
C40.02092 (12)0.24228 (16)0.34674 (8)0.0223 (3)
C5−0.08460 (12)0.32173 (16)0.32039 (8)0.0223 (3)
C30.10997 (11)0.31895 (15)0.39506 (8)0.0191 (3)
C6−0.10163 (11)0.47803 (16)0.34134 (8)0.0197 (3)
C7−0.01078 (12)0.55645 (15)0.38947 (8)0.0192 (3)
C80.09313 (12)0.47800 (16)0.41617 (8)0.0191 (3)
C90.51071 (12)0.51201 (16)0.63818 (8)0.0212 (3)
C100.61312 (13)0.47347 (18)0.68703 (8)0.0254 (3)
C110.66528 (13)0.58702 (18)0.73831 (8)0.0266 (3)
C120.61602 (13)0.73693 (18)0.74239 (9)0.0261 (3)
C130.51291 (13)0.77472 (18)0.69408 (9)0.0276 (3)
C140.46044 (13)0.66315 (17)0.64255 (9)0.0247 (3)
C150.05810 (13)0.80047 (18)0.44801 (9)0.0254 (3)
C16−0.24398 (16)0.9612 (2)0.37071 (10)0.0355 (4)
H10.2343 (13)0.1272 (19)0.4021 (8)0.021 (4)*
H20.0297 (14)0.131 (2)0.3319 (9)0.028 (4)*
H3−0.1460 (14)0.269 (2)0.2890 (9)0.028 (4)*
H40.1569 (14)0.5318 (19)0.4486 (9)0.026 (4)*
H50.6477 (14)0.370 (2)0.6856 (9)0.030 (4)*
H60.7391 (15)0.5623 (19)0.7720 (9)0.032 (4)*
H70.6504 (15)0.818 (2)0.7786 (10)0.031 (4)*
H80.4727 (15)0.883 (2)0.6956 (9)0.032 (4)*
H90.3903 (15)0.688 (2)0.6076 (10)0.031 (4)*
H100.0725 (14)0.757 (2)0.5024 (10)0.029 (4)*
H110.1347 (15)0.7966 (19)0.4238 (9)0.027 (4)*
H120.0276 (15)0.910 (2)0.4506 (9)0.033 (4)*
H130.3793 (16)0.438 (2)0.5638 (9)0.030 (4)*
H140.4096 (15)0.115 (2)0.4769 (10)0.035 (5)*
H15−0.2449 (17)0.513 (2)0.2819 (11)0.049 (6)*
H16−0.2038 (19)0.922 (3)0.4223 (14)0.067 (6)*
H17−0.321 (2)0.914 (3)0.3632 (12)0.064 (7)*
H18−0.2597 (19)1.079 (3)0.3773 (12)0.061 (6)*
H19−0.1477 (18)0.846 (3)0.3092 (12)0.052 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02158 (19)0.0286 (2)0.0418 (2)0.00936 (14)−0.00942 (15)−0.01015 (16)
O10.0196 (5)0.0227 (5)0.0306 (6)0.0036 (4)−0.0071 (4)−0.0031 (4)
O20.0194 (5)0.0176 (5)0.0300 (5)0.0020 (4)−0.0043 (4)−0.0050 (4)
O30.0264 (5)0.0231 (5)0.0297 (6)0.0045 (4)−0.0013 (4)0.0023 (4)
N10.0179 (6)0.0204 (6)0.0242 (6)0.0045 (4)−0.0020 (4)−0.0017 (5)
N20.0173 (5)0.0205 (6)0.0220 (6)0.0043 (4)0.0000 (4)0.0018 (5)
N30.0180 (6)0.0229 (6)0.0291 (6)0.0048 (5)−0.0061 (5)−0.0042 (5)
C10.0190 (6)0.0214 (7)0.0214 (7)0.0008 (5)0.0008 (5)0.0011 (5)
C20.0209 (7)0.0190 (7)0.0208 (7)0.0014 (5)0.0006 (5)−0.0001 (5)
C40.0239 (7)0.0177 (7)0.0245 (7)0.0011 (5)−0.0010 (6)−0.0016 (5)
C50.0212 (7)0.0202 (7)0.0240 (7)−0.0013 (5)−0.0043 (5)−0.0015 (5)
C30.0184 (6)0.0199 (7)0.0187 (6)0.0013 (5)0.0005 (5)0.0011 (5)
C60.0171 (6)0.0210 (7)0.0206 (7)0.0019 (5)−0.0006 (5)0.0022 (5)
C70.0208 (6)0.0158 (6)0.0207 (7)0.0002 (5)0.0018 (5)0.0000 (5)
C80.0177 (6)0.0200 (7)0.0191 (6)−0.0003 (5)−0.0005 (5)−0.0005 (5)
C90.0199 (7)0.0220 (7)0.0216 (7)−0.0013 (5)0.0019 (5)−0.0001 (5)
C100.0244 (7)0.0237 (7)0.0271 (7)0.0033 (6)−0.0029 (6)−0.0011 (6)
C110.0235 (7)0.0300 (8)0.0251 (7)−0.0009 (6)−0.0028 (6)−0.0010 (6)
C120.0264 (7)0.0269 (7)0.0255 (7)−0.0059 (6)0.0042 (6)−0.0050 (6)
C130.0277 (7)0.0238 (7)0.0314 (8)0.0022 (6)0.0038 (6)−0.0026 (6)
C140.0218 (7)0.0251 (7)0.0268 (7)0.0038 (6)0.0007 (6)−0.0019 (6)
C150.0228 (7)0.0218 (7)0.0305 (8)−0.0009 (6)−0.0025 (6)−0.0068 (6)
C160.0295 (9)0.0420 (10)0.0355 (9)0.0070 (7)0.0059 (7)0.0097 (7)
Geometric parameters (Å, º) top
S1—C11.6832 (13)C3—C81.4055 (18)
O1—C61.3630 (15)C6—C71.4102 (18)
O1—H150.86 (2)C7—C81.3753 (18)
O2—C71.3703 (15)C8—H40.973 (16)
O2—C151.4308 (16)C9—C101.3906 (19)
O3—C161.421 (2)C9—C141.3964 (19)
O3—H190.83 (2)C10—C111.391 (2)
N1—C11.3579 (17)C10—H50.952 (17)
N1—N21.3766 (15)C11—C121.382 (2)
N1—H140.896 (19)C11—H60.983 (17)
N2—C21.2843 (17)C12—C131.390 (2)
N3—C11.3440 (18)C12—H70.975 (17)
N3—C91.4130 (17)C13—C141.383 (2)
N3—H130.866 (18)C13—H81.020 (17)
C2—C31.4597 (18)C14—H90.964 (17)
C2—H10.993 (16)C15—H101.004 (17)
C4—C31.3918 (18)C15—H110.991 (17)
C4—C51.3925 (19)C15—H120.983 (18)
C4—H20.975 (17)C16—H161.01 (2)
C5—C61.3831 (19)C16—H170.95 (2)
C5—H30.941 (16)C16—H181.01 (2)
C6—O1—H15109.5 (13)C7—C8—H4121.0 (9)
C7—O2—C15116.58 (10)C3—C8—H4118.9 (9)
C16—O3—H19108.7 (15)C10—C9—C14119.45 (13)
C1—N1—N2119.57 (11)C10—C9—N3124.81 (13)
C1—N1—H14119.2 (11)C14—C9—N3115.72 (12)
N2—N1—H14121.2 (11)C11—C10—C9119.51 (14)
C2—N2—N1116.69 (11)C11—C10—H5119.9 (10)
C1—N3—C9132.57 (12)C9—C10—H5120.6 (10)
C1—N3—H13111.3 (11)C12—C11—C10121.10 (14)
C9—N3—H13116.0 (11)C12—C11—H6118.6 (10)
N3—C1—N1114.01 (12)C10—C11—H6120.3 (10)
N3—C1—S1127.69 (10)C11—C12—C13119.31 (14)
N1—C1—S1118.30 (10)C11—C12—H7122.3 (10)
N2—C2—C3120.52 (12)C13—C12—H7118.4 (10)
N2—C2—H1120.5 (8)C14—C13—C12120.19 (14)
C3—C2—H1118.9 (8)C14—C13—H8117.8 (9)
C3—C4—C5120.31 (13)C12—C13—H8122.0 (9)
C3—C4—H2121.1 (9)C13—C14—C9120.44 (13)
C5—C4—H2118.6 (9)C13—C14—H9121.3 (10)
C6—C5—C4120.41 (12)C9—C14—H9118.3 (10)
C6—C5—H3119.0 (10)O2—C15—H10110.1 (9)
C4—C5—H3120.5 (10)O2—C15—H11112.1 (9)
C4—C3—C8119.39 (12)H10—C15—H11108.6 (13)
C4—C3—C2119.98 (12)O2—C15—H12105.8 (10)
C8—C3—C2120.62 (12)H10—C15—H12108.6 (14)
O1—C6—C5123.84 (12)H11—C15—H12111.6 (14)
O1—C6—C7116.85 (12)O3—C16—H16114.0 (13)
C5—C6—C7119.30 (12)O3—C16—H17113.2 (13)
O2—C7—C8125.07 (12)H16—C16—H17107.7 (18)
O2—C7—C6114.46 (11)O3—C16—H18109.9 (12)
C8—C7—C6120.46 (12)H16—C16—H18106.6 (18)
C7—C8—C3120.10 (12)H17—C16—H18104.8 (18)
C1—N1—N2—N20.00 (10)O2—O2—C7—C60.0 (4)
C1—N1—N2—C2−179.57 (12)C15—O2—C7—C6−175.37 (12)
N2—N1—N2—C20 (33)O1—C6—C7—O2−1.49 (17)
C9—N3—C1—N1−175.91 (13)O1—C6—C7—O2−1.49 (17)
C9—N3—C1—S13.6 (2)C5—C6—C7—O2177.86 (12)
N2—N1—C1—N34.88 (18)O1—C6—C7—O2−1.49 (17)
N2—N1—C1—N34.88 (18)O1—C6—C7—O2−1.49 (17)
N2—N1—C1—S1−174.68 (10)C5—C6—C7—O2177.86 (12)
N2—N1—C1—S1−174.68 (10)O1—C6—C7—C8179.85 (12)
N1—N2—C2—N20 (78)O1—C6—C7—C8179.85 (12)
N2—N2—C2—C30.00 (13)C5—C6—C7—C8−0.8 (2)
N1—N2—C2—C3−178.52 (11)O2—C7—C8—C3−177.97 (12)
C3—C4—C5—C60.6 (2)O2—C7—C8—C3−177.97 (12)
C5—C4—C3—C8−0.9 (2)C6—C7—C8—C30.5 (2)
C5—C4—C3—C2178.81 (13)C4—C3—C8—C70.3 (2)
N2—C2—C3—C4−171.87 (13)C2—C3—C8—C7−179.37 (12)
N2—C2—C3—C4−171.87 (13)C1—N3—C9—C10−17.0 (2)
N2—C2—C3—C87.8 (2)C1—N3—C9—C14164.40 (15)
N2—C2—C3—C87.8 (2)C14—C9—C10—C11−1.3 (2)
O1—O1—C6—C50.00 (5)N3—C9—C10—C11−179.84 (13)
O1—O1—C6—C70.00 (7)C9—C10—C11—C121.0 (2)
C4—C5—C6—O1179.54 (13)C10—C11—C12—C13−0.3 (2)
C4—C5—C6—O1179.54 (13)C11—C12—C13—C140.0 (2)
C4—C5—C6—C70.2 (2)C12—C13—C14—C9−0.4 (2)
C15—O2—C7—O20 (24)C10—C9—C14—C131.0 (2)
O2—O2—C7—C80.0 (4)N3—C9—C14—C13179.68 (13)
C15—O2—C7—C83.22 (19)C7—O2—C15—O20 (76)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H13···N20.866 (18)2.082 (17)2.5865 (16)116.4 (14)
N1—H14···S1i0.896 (19)2.530 (19)3.4033 (13)165.2 (15)
O1—H15···O3ii0.86 (2)1.81 (2)2.6562 (14)167.7 (19)
O3—H19···O20.83 (2)2.26 (2)2.8853 (14)132.1 (18)
O3—H19···O10.83 (2)2.46 (2)3.1645 (15)144.2 (18)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1/2, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H13···N20.866 (18)2.082 (17)2.5865 (16)116.4 (14)
N1—H14···S1i0.896 (19)2.530 (19)3.4033 (13)165.2 (15)
O1—H15···O3ii0.86 (2)1.81 (2)2.6562 (14)167.7 (19)
O3—H19···O20.83 (2)2.26 (2)2.8853 (14)132.1 (18)
O3—H19···O10.83 (2)2.46 (2)3.1645 (15)144.2 (18)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1/2, y−1/2, −z+1/2.
 

Acknowledgements

BRSF thanks CNPq/UFS for the award of a PIBIC scholarship.

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ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages o313-o314
https://doi.org/10.1107/S2056989015007227
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