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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 o295-o296
https://doi.org/10.1107/S2056989015005708

Crystal structure of febuxostat–acetic acid (1/1)

Min Wu,a Xiu-Rong Hu,a Jian-Ming Gua* and Gu-Ping Tanga

aChemistry Department, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China
*Correspondence e-mail: tangguping@zju.edu.cn

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 28 January 2015; accepted 20 March 2015; online 9 April 2015)

The asymmetric unit of the title compound [systematic name: 2-(3-cyano-4-iso­butyl­oxyphen­yl)-4-methyl­thia­zole-5-carb­oxy­lic acid–acetic acid (1/1)], C16H16N2O3S·CH3COOH, contains a febuxostat mol­ecule and an acetic acid mol­ecule. In the febuxostat mol­ecule, the thia­zole ring is nearly coplanar with the benzene ring [dihedral angle = 3.24 (2)°]. In the crystal, the febuxostat and acetic acid mol­ecules are linked by O—H⋯O, O—H⋯N hydrogen bonds and weak C—H⋯O hydrogen bonds, forming supra­molecular chains propagating along the b-axis direction. π–π stacking is observed between nearly parallel thia­zole and benzene rings of adjacent mol­ecules; the centroid-to-centroid distances are 3.8064 (17) and 3.9296 (17) Å.

CCDC reference: 1055245

Similar articles

1. Related literature

For general apllications of febuxostat in medicine, see: Pascual et al. (2009[Pascual, E., Sivera, F., Yasothan, U. & Kirkpatrick, P. (2009). Nat. Rev. Drug Discov. 8, 191-192.]); Kataoka et al. (2015[Kataoka, H., Yang, K. & Rock, K. L. (2015). Eur. J. Pharmacol. 746, 174-179.]); Gray & Walters-Smith (2011[Gray, C. L. & Walters-Smith, N. E. (2011). Am. J. Health Syst. Pharm. 68, 389-398.]). For the synthesis, polymorphism, stability and bioavailabitily of febuxostat, see: Hiramatsu et al. (2000[Hiramatsu, T., Matsumoto, K. & Watanabe, K. (2000). China Patent CN1275126.]); Maddileti et al. (2013[Maddileti, D., Jayabun, S. K. & Nangia, A. (2013). Cryst. Growth Des. 13, 3188-3196.]). For the crystal structures of febuxostat pyridine solvate and febuxostat methanol solvate, see: Zhu et al. (2009[Zhu, X., Wang, Y. & Lu, T. (2009). Acta Cryst. E65, o2603.]); Jiang et al. (2011[Jiang, Q.-Y., Qian, J.-J., Gu, J.-M., Tang, G.-P. & Hu, X.-R. (2011). Acta Cryst. E67, o1232.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C16H16N2O3S·C2H4O2

  • Mr = 376.42

  • Triclinic, [P \overline 1]

  • a = 7.684 (2) Å

  • b = 10.580 (3) Å

  • c = 12.059 (3) Å

  • α = 84.897 (5)°

  • β = 84.674 (4)°

  • γ = 71.081 (5)°

  • V = 921.6 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 296 K

  • 0.51 × 0.30 × 0.24 mm

2.2. Data collection

  • Rigaku R-AXIS RAPID/ZJUG diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.890, Tmax = 0.952

  • 7415 measured reflections

  • 3397 independent reflections

  • 2749 reflections with I > 2σ(I)

  • Rint = 0.026

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.123

  • S = 1.00

  • 3397 reflections

  • 241 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O5i 0.82 1.87 2.691 (2) 177
O4—H4⋯N1 0.82 2.05 2.800 (3) 152
C10—H10⋯O2ii 0.93 2.30 3.192 (3) 162
C11—H11⋯O5 0.93 2.45 3.344 (3) 161
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: PROCESS-AUTO (Rigaku, 2006[Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007[Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

CCDC reference: 1055245

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015005708/xu5836sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015005708/xu5836Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015005708/xu5836Isup3.cml

checkCIF report


Comment top

Febuxostat, an inhibitor of xanthine oxidase, was granted marketing authorization by the European Commission for the treatment of chronic hyperuricaemia in May 2008 (Pascual et al., 2009). Gout is one of the oldest meta-bolic diseases described, frequently categorized as a type of inflammatory arthritis, however, febuxostat is efficacious as a second-line therapy in lowering serum uric acid levels in patients with gout (Gray & Walters-Smith, 2011). According to a recent report, febuxostat has the potential usefulness for reducing cell death-induced inflammation (Kataoka et al., 2015). For the important role of febuxotat, many papers and patents have been reported on the synthesis, polymorphism, stability and bioavailabitily of this drug (Hiramatsu et al., 2000). For the crystal structure of febuxostat form Q, febuxostat pyridine solvate and methanol solvate has been reported. In the present study, we report the crystal structure of febuxostat acetic acid solvate. The asymmetric unit consists of one febuxostat molecule and one acetic molecule (Fig. 1), which is linked by intramolecular hydrogen bond O4—H4···N1. The benzene and thiazole rings of the febuxostat molecule are alomost coplanar with the dihedral angle of 3.24 (2)°, which is comparable with that of found (Jiang et al., 2011). The carbonyl group is twist slightly to the connected benzene ring plane, as indicated by torsion angles O2—C3—C4—S1 and O1—C3—C4—C2 of 7.2 (3)° and 10.4 (4)°, respectively, which is different to that of febuxostat methanol solvate and febuxostat pyridine solvate. The cyano group is not coplanar to the benzene ring as indicated by torsion angle C7—C8—C12—N2 and C9—C8—C12—N2. Conformation of the febuxostat molecule in the structure of title compound is different silghtly to that of febuxostat methanol solvate and febuxostat pyridine solvate. In the crystal structure, acetic acid molecule is linked to the febuxostat via intermolecular hydrogen bond O1—H1···O5 i [symmetric code: (i)x,y + 1,z] hydrogen bond and intramolecular hydrogen bond O4—H4···N1 (Table 1). In this way, an infinite molecule chain is formed stretching along the the b axis.

Related literature top

For general apllications of febuxostat in medicine, see: Pascual et al. (2009); Kataoka et al. (2015); Gray & Walters-Smith (2011). For the synthesis, polymorphism, stability and bioavailabitily of febuxostat, see: Hiramatsu et al. (2000); Maddileti et al. (2013). For the crystal structures of febuxostat pyridine solvate and febuxostat methanol solvate, see: Zhu et al. (2009); Jiang et al. (2011).

Experimental top

The crude product supplied by Zhejiang Huadong Pharmaceutical Co., Ltd, was recrystallized from the acetic acid solution giving colourless crystals suitable for X-ray diffraction.

Refinement top

All H atoms were placed in calculated positions with O—H = 0.82 Å and C—H = 0.93–0.98 Å and included in the refinement in riding model, with Uiso(H)= 1.2Ueq or 1.5Ueq(carrier atom).

Structure description top

Febuxostat, an inhibitor of xanthine oxidase, was granted marketing authorization by the European Commission for the treatment of chronic hyperuricaemia in May 2008 (Pascual et al., 2009). Gout is one of the oldest meta-bolic diseases described, frequently categorized as a type of inflammatory arthritis, however, febuxostat is efficacious as a second-line therapy in lowering serum uric acid levels in patients with gout (Gray & Walters-Smith, 2011). According to a recent report, febuxostat has the potential usefulness for reducing cell death-induced inflammation (Kataoka et al., 2015). For the important role of febuxotat, many papers and patents have been reported on the synthesis, polymorphism, stability and bioavailabitily of this drug (Hiramatsu et al., 2000). For the crystal structure of febuxostat form Q, febuxostat pyridine solvate and methanol solvate has been reported. In the present study, we report the crystal structure of febuxostat acetic acid solvate. The asymmetric unit consists of one febuxostat molecule and one acetic molecule (Fig. 1), which is linked by intramolecular hydrogen bond O4—H4···N1. The benzene and thiazole rings of the febuxostat molecule are alomost coplanar with the dihedral angle of 3.24 (2)°, which is comparable with that of found (Jiang et al., 2011). The carbonyl group is twist slightly to the connected benzene ring plane, as indicated by torsion angles O2—C3—C4—S1 and O1—C3—C4—C2 of 7.2 (3)° and 10.4 (4)°, respectively, which is different to that of febuxostat methanol solvate and febuxostat pyridine solvate. The cyano group is not coplanar to the benzene ring as indicated by torsion angle C7—C8—C12—N2 and C9—C8—C12—N2. Conformation of the febuxostat molecule in the structure of title compound is different silghtly to that of febuxostat methanol solvate and febuxostat pyridine solvate. In the crystal structure, acetic acid molecule is linked to the febuxostat via intermolecular hydrogen bond O1—H1···O5 i [symmetric code: (i)x,y + 1,z] hydrogen bond and intramolecular hydrogen bond O4—H4···N1 (Table 1). In this way, an infinite molecule chain is formed stretching along the the b axis.

For general apllications of febuxostat in medicine, see: Pascual et al. (2009); Kataoka et al. (2015); Gray & Walters-Smith (2011). For the synthesis, polymorphism, stability and bioavailabitily of febuxostat, see: Hiramatsu et al. (2000); Maddileti et al. (2013). For the crystal structures of febuxostat pyridine solvate and febuxostat methanol solvate, see: Zhu et al. (2009); Jiang et al. (2011).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound (I) showing atom-labelling scheme.
[Figure 2] Fig. 2. Part of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
2-(3-Cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid–acetic acid (1/1) top
Crystal data top
C16H16N2O3S·C2H4O2Z = 2
Mr = 376.42F(000) = 396
Triclinic, P1Dx = 1.356 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.684 (2) ÅCell parameters from 2789 reflections
b = 10.580 (3) Åθ = 3.2–27.4°
c = 12.059 (3) ŵ = 0.21 mm−1
α = 84.897 (5)°T = 296 K
β = 84.674 (4)°Chunk, colorless
γ = 71.081 (5)°0.51 × 0.30 × 0.24 mm
V = 921.6 (4) Å3
Data collection top
Rigaku R-AXIS RAPID/ZJUG
diffractometer		3397 independent reflections
Radiation source: rolling anode2749 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 10.00 pixels mm-1θmax = 25.5°, θmin = 3.2°
ω scansh = −8→9
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −12→12
Tmin = 0.890, Tmax = 0.952l = −14→14
7415 measured reflections
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0641P)2 + 0.4268P]
where P = (Fo2 + 2Fc2)/3
3397 reflections(Δ/σ)max < 0.001
241 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C16H16N2O3S·C2H4O2γ = 71.081 (5)°
Mr = 376.42V = 921.6 (4) Å3
Triclinic, P1Z = 2
a = 7.684 (2) ÅMo Kα radiation
b = 10.580 (3) ŵ = 0.21 mm−1
c = 12.059 (3) ÅT = 296 K
α = 84.897 (5)°0.51 × 0.30 × 0.24 mm
β = 84.674 (4)°
Data collection top
Rigaku R-AXIS RAPID/ZJUG
diffractometer		3397 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2749 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.952Rint = 0.026
7415 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.00Δρmax = 0.25 e Å−3
3397 reflectionsΔρmin = −0.26 e Å−3
241 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
S10.72628 (8)0.73569 (5)0.50085 (4)0.03662 (17)
O10.5945 (3)1.02293 (15)0.26948 (14)0.0507 (4)
H10.58891.10160.27050.076*
O20.7074 (3)1.00765 (16)0.43526 (15)0.0584 (5)
O30.8936 (2)0.12754 (14)0.74240 (13)0.0435 (4)
O40.5922 (3)0.46989 (15)0.17802 (14)0.0538 (5)
H40.62210.48210.23870.081*
O50.5837 (3)0.28003 (15)0.26573 (13)0.0511 (4)
N10.6762 (2)0.60007 (15)0.34796 (13)0.0305 (4)
N20.9313 (4)0.3647 (3)0.90533 (19)0.0707 (7)
C30.6693 (3)0.81547 (19)0.37300 (17)0.0324 (5)
C20.6483 (3)0.72860 (18)0.30167 (17)0.0304 (4)
C10.7188 (3)0.59016 (18)0.45268 (16)0.0291 (4)
C40.6599 (3)0.9576 (2)0.36255 (18)0.0364 (5)
C50.6022 (3)0.7595 (2)0.18262 (18)0.0416 (5)
H5A0.48350.75080.17470.062*
H5B0.69380.69810.13650.062*
H5C0.59970.84930.16010.062*
C60.7591 (3)0.46731 (19)0.52647 (16)0.0299 (4)
C110.7480 (3)0.3481 (2)0.49263 (17)0.0333 (5)
H110.71060.34640.42180.040*
C100.7910 (3)0.2323 (2)0.56132 (18)0.0361 (5)
H100.78360.15370.53630.043*
C90.8457 (3)0.2333 (2)0.66802 (17)0.0332 (5)
C80.8528 (3)0.3538 (2)0.70422 (17)0.0332 (5)
C70.8122 (3)0.4681 (2)0.63359 (17)0.0337 (5)
H70.82050.54680.65800.040*
C130.8752 (3)0.0017 (2)0.71520 (19)0.0412 (5)
H13A0.9542−0.03120.64950.049*
H13B0.74870.01390.70030.049*
C140.9314 (3)−0.0965 (2)0.8147 (2)0.0450 (6)
H141.0592−0.10620.82770.054*
C150.8132 (4)−0.0512 (3)0.9196 (2)0.0650 (8)
H15A0.81970.03420.93620.098*
H15B0.8569−0.11540.98040.098*
H15C0.6878−0.04340.90910.098*
C160.9239 (4)−0.2326 (2)0.7854 (3)0.0605 (7)
H16A0.8005−0.22420.76920.091*
H16B0.9601−0.29660.84740.091*
H16C1.0064−0.26220.72120.091*
C120.8996 (3)0.3588 (2)0.81619 (19)0.0440 (5)
C170.5719 (3)0.3514 (2)0.18152 (18)0.0371 (5)
C180.5320 (5)0.3165 (3)0.0724 (2)0.0676 (8)
H18A0.53750.22430.07690.101*
H18B0.62170.33050.01590.101*
H18C0.41110.37220.05380.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0516 (3)0.0284 (3)0.0330 (3)−0.0157 (2)−0.0089 (2)−0.0002 (2)
O10.0769 (12)0.0284 (8)0.0533 (10)−0.0232 (8)−0.0232 (9)0.0079 (7)
O20.0934 (14)0.0360 (9)0.0574 (11)−0.0312 (9)−0.0266 (10)−0.0004 (8)
O30.0615 (10)0.0317 (8)0.0401 (9)−0.0190 (7)−0.0145 (7)0.0104 (6)
O40.0965 (14)0.0329 (8)0.0406 (9)−0.0315 (9)−0.0159 (9)0.0059 (7)
O50.0845 (13)0.0324 (8)0.0425 (9)−0.0267 (8)−0.0148 (8)0.0068 (7)
N10.0390 (9)0.0238 (8)0.0294 (9)−0.0111 (7)−0.0063 (7)0.0025 (6)
N20.0975 (19)0.0752 (16)0.0407 (13)−0.0255 (15)−0.0214 (12)−0.0011 (11)
C30.0372 (11)0.0281 (10)0.0332 (11)−0.0122 (8)−0.0059 (9)0.0028 (8)
C20.0341 (10)0.0246 (9)0.0332 (11)−0.0110 (8)−0.0032 (8)0.0018 (8)
C10.0295 (10)0.0254 (9)0.0320 (10)−0.0089 (8)−0.0008 (8)−0.0012 (8)
C40.0422 (12)0.0291 (10)0.0406 (12)−0.0153 (9)−0.0052 (9)0.0013 (9)
C50.0627 (14)0.0295 (10)0.0352 (12)−0.0177 (10)−0.0129 (10)0.0063 (9)
C60.0314 (10)0.0274 (10)0.0302 (10)−0.0090 (8)−0.0017 (8)0.0008 (8)
C110.0388 (11)0.0327 (10)0.0304 (10)−0.0141 (9)−0.0061 (9)0.0023 (8)
C100.0462 (12)0.0292 (10)0.0364 (11)−0.0161 (9)−0.0074 (9)0.0009 (9)
C90.0367 (11)0.0303 (10)0.0337 (11)−0.0136 (9)−0.0042 (9)0.0057 (8)
C80.0375 (11)0.0329 (10)0.0286 (10)−0.0104 (9)−0.0039 (8)0.0009 (8)
C70.0404 (11)0.0279 (10)0.0338 (11)−0.0120 (9)−0.0031 (9)−0.0017 (8)
C130.0506 (13)0.0313 (11)0.0437 (13)−0.0173 (10)−0.0039 (10)0.0049 (9)
C140.0450 (12)0.0355 (11)0.0528 (14)−0.0126 (10)−0.0094 (11)0.0110 (10)
C150.088 (2)0.0519 (15)0.0481 (15)−0.0164 (15)−0.0039 (14)0.0141 (12)
C160.0697 (17)0.0333 (12)0.0743 (19)−0.0146 (12)−0.0043 (15)0.0111 (12)
C120.0577 (14)0.0389 (12)0.0357 (13)−0.0157 (11)−0.0094 (10)0.0032 (9)
C170.0473 (12)0.0272 (10)0.0388 (12)−0.0148 (9)−0.0030 (9)−0.0010 (9)
C180.119 (3)0.0564 (16)0.0429 (15)−0.0473 (17)−0.0126 (15)−0.0017 (12)
Geometric parameters (Å, º) top
S1—C31.713 (2)C11—H110.9300
S1—C11.713 (2)C10—C91.392 (3)
O1—C41.316 (3)C10—H100.9300
O1—H10.8200C9—C81.403 (3)
O2—C41.204 (3)C8—C71.381 (3)
O3—C91.344 (2)C8—C121.439 (3)
O3—C131.452 (3)C7—H70.9300
O4—C171.309 (3)C13—C141.512 (3)
O4—H40.8200C13—H13A0.9700
O5—C171.203 (3)C13—H13B0.9700
N1—C11.321 (3)C14—C151.506 (4)
N1—C21.380 (2)C14—C161.533 (3)
N2—C121.135 (3)C14—H140.9800
C3—C21.369 (3)C15—H15A0.9600
C3—C41.477 (3)C15—H15B0.9600
C2—C51.493 (3)C15—H15C0.9600
C1—C61.470 (3)C16—H16A0.9600
C5—H5A0.9600C16—H16B0.9600
C5—H5B0.9600C16—H16C0.9600
C5—H5C0.9600C17—C181.482 (3)
C6—C111.389 (3)C18—H18A0.9600
C6—C71.392 (3)C18—H18B0.9600
C11—C101.380 (3)C18—H18C0.9600
C3—S1—C189.55 (10)C8—C7—C6120.94 (19)
C4—O1—H1109.5C8—C7—H7119.5
C9—O3—C13118.74 (17)C6—C7—H7119.5
C17—O4—H4109.5O3—C13—C14107.20 (18)
C1—N1—C2110.89 (16)O3—C13—H13A110.3
C2—C3—C4134.5 (2)C14—C13—H13A110.3
C2—C3—S1110.65 (15)O3—C13—H13B110.3
C4—C3—S1114.82 (15)C14—C13—H13B110.3
C3—C2—N1114.23 (18)H13A—C13—H13B108.5
C3—C2—C5126.75 (18)C15—C14—C13112.9 (2)
N1—C2—C5119.01 (17)C15—C14—C16110.9 (2)
N1—C1—C6125.29 (17)C13—C14—C16108.2 (2)
N1—C1—S1114.68 (14)C15—C14—H14108.2
C6—C1—S1120.03 (15)C13—C14—H14108.2
O2—C4—O1123.93 (19)C16—C14—H14108.2
O2—C4—C3121.4 (2)C14—C15—H15A109.5
O1—C4—C3114.69 (18)C14—C15—H15B109.5
C2—C5—H5A109.5H15A—C15—H15B109.5
C2—C5—H5B109.5C14—C15—H15C109.5
H5A—C5—H5B109.5H15A—C15—H15C109.5
C2—C5—H5C109.5H15B—C15—H15C109.5
H5A—C5—H5C109.5C14—C16—H16A109.5
H5B—C5—H5C109.5C14—C16—H16B109.5
C11—C6—C7118.10 (18)H16A—C16—H16B109.5
C11—C6—C1122.16 (18)C14—C16—H16C109.5
C7—C6—C1119.74 (18)H16A—C16—H16C109.5
C10—C11—C6121.79 (19)H16B—C16—H16C109.5
C10—C11—H11119.1N2—C12—C8178.0 (3)
C6—C11—H11119.1O5—C17—O4122.5 (2)
C11—C10—C9119.94 (19)O5—C17—C18124.4 (2)
C11—C10—H10120.0O4—C17—C18113.11 (19)
C9—C10—H10120.0C17—C18—H18A109.5
O3—C9—C10125.95 (18)C17—C18—H18B109.5
O3—C9—C8115.24 (18)H18A—C18—H18B109.5
C10—C9—C8118.81 (18)C17—C18—H18C109.5
C7—C8—C9120.38 (19)H18A—C18—H18C109.5
C7—C8—C12119.81 (19)H18B—C18—H18C109.5
C9—C8—C12119.80 (18)
C1—S1—C3—C2−0.09 (16)S1—C1—C6—C7−3.2 (3)
C1—S1—C3—C4−178.19 (16)C7—C6—C11—C10−1.1 (3)
C4—C3—C2—N1177.9 (2)C1—C6—C11—C10178.15 (18)
S1—C3—C2—N10.3 (2)C6—C11—C10—C90.6 (3)
C4—C3—C2—C5−1.3 (4)C13—O3—C9—C10−5.0 (3)
S1—C3—C2—C5−178.87 (18)C13—O3—C9—C8174.90 (18)
C1—N1—C2—C3−0.4 (2)C11—C10—C9—O3−179.0 (2)
C1—N1—C2—C5178.84 (18)C11—C10—C9—C81.1 (3)
C2—N1—C1—C6−179.40 (18)O3—C9—C8—C7177.91 (18)
C2—N1—C1—S10.3 (2)C10—C9—C8—C7−2.2 (3)
C3—S1—C1—N1−0.13 (16)O3—C9—C8—C12−3.1 (3)
C3—S1—C1—C6179.60 (16)C10—C9—C8—C12176.8 (2)
C2—C3—C4—O2−170.3 (2)C9—C8—C7—C61.6 (3)
S1—C3—C4—O27.2 (3)C12—C8—C7—C6−177.3 (2)
C2—C3—C4—O110.4 (4)C11—C6—C7—C80.0 (3)
S1—C3—C4—O1−172.07 (16)C1—C6—C7—C8−179.29 (18)
N1—C1—C6—C11−2.8 (3)C9—O3—C13—C14−177.85 (18)
S1—C1—C6—C11177.53 (15)O3—C13—C14—C1560.1 (3)
N1—C1—C6—C7176.48 (19)O3—C13—C14—C16−176.75 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O5i0.821.872.691 (2)177
O4—H4···N10.822.052.800 (3)152
C10—H10···O2ii0.932.303.192 (3)162
C11—H11···O50.932.453.344 (3)161
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O5i0.821.872.691 (2)177
O4—H4···N10.822.052.800 (3)152
C10—H10···O2ii0.932.303.192 (3)162
C11—H11···O50.932.453.344 (3)161
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.
 

Acknowledgements

The project was supported by the Analysis and Measurement Foundation of Zhejiang Province, China (2014 C37055).

References

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ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages o295-o296
https://doi.org/10.1107/S2056989015005708
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