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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 70| Part 7| July 2014| Pages o745-o746
https://doi.org/10.1107/S1600536814012495

Ethyl 2-[({[4-amino-5-cyano-6-(methyl­sulfan­yl)pyridin-2-yl]carbamo­yl}meth­yl)sulfan­yl]acetate monohydrate

Mehmet Akkurt,a Joel T. Mague,b Shaaban K. Mohamed,c,d Bahgat R. M. Husseine and Mustafa R. Albayatif*

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 27 May 2014; accepted 29 May 2014; online 4 June 2014)

The title compound, C13H16N4O3S2·H2O, crystallizes in a `folded' conformation with the ester group lying over the carbamoyl moiety, with one solvent water mol­ecule. The mol­ecular conformation is stabilized by an intra­molecular C—H⋯O hydrogen bond, and an N—H⋯O hydrogen-bonding inter­action involving the lattice water mol­ecule. The packing involves N—H⋯N, N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds and consists of tilted layers running approximately parallel to the c axis, with the ester groups on the outer sides of the layers and with channels running parallel to (101).

CCDC reference: 1005734

Related literature

For the synthesis of amino-cyano pyridines, see: Shi et al. (2005[Shi, F., Shujiang Tu, S., Fang, F. & Li, T. (2005). Arkivoc, i, 137-142.]). For pyridines as inter­mediates in the synthesis of different heterocyclic compounds, see: Konda et al. (2010[Konda, S. G., Khedkar, V. T. & Dawane, B. S. (2010). J. Chem. Pharm. Res. 2, 1-6.]). For the pharmaceutical activity of functionalized pyridine derivatives, see: Dorigo et al. (1993[Dorigo, P., Gaion, R. M., Belluco, P., Fraccarollo, D., Maragano, I., Bombien, G., Benelollo, F., Mostil, L. & Orsini, F. (1993). J. Med. Chem. 36, 2475-2484.]); Dolle et al. (1995[Dolle, V., Nguyen, E. C. H., Aubertin, A. M., Kirm, A. M., Andreola, L., Jamieson, G., Tarrago-Litvak, L. & Bisagni, E. (1995). J. Med. Chem. 38, 4679-4686.]); Murata et al. (2003[Murata, T., Shimada, M., Sakakibara, S., Yoshino, T. & Kadono, H. (2003). Bioorg. Med. Chem. Lett. 13, 913-918.]). For industrial applications of pyridine compounds, see: Lohray et al. (2004[Lohray, B. B., Lohray, V. B. & Srivastava, B. K. (2004). Bioorg. Med. Chem. 17, 4557-4564.]); Merja et al. (2004[Merja, B. C., Joshi, A. M. & Parikh, K. A. (2004). Indian J. Chem. Sect. B, 4, 909-912.]); Chaki et al. (1995[Chaki, H., Yamabe, H., Sugano, M., Morita, S., Bessho, T., Tabata, R., Saito, K. I., Egawa, M., Tobe, A. & Morinaka, Y. (1995). Bioorg. Med. Chem. Lett. 5, 1495-1500.]); Thomae et al. (2007[Thomae, D., Kirsch, G. & Seck, P. (2007). Synthesis, 7, 1027-1032.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C13H16N4O3S2·H2O

  • Mr = 358.45

  • Triclinic, [P \overline 1]

  • a = 9.0806 (12) Å

  • b = 9.2444 (12) Å

  • c = 10.7856 (14) Å

  • α = 101.843 (2)°

  • β = 100.1750 (19)°

  • γ = 105.9480 (19)°

  • V = 825.48 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.35 mm−1

  • T = 150 K

  • 0.26 × 0.26 × 0.12 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.83, Tmax = 0.96

  • 15313 measured reflections

  • 4292 independent reflections

  • 3773 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.099

  • S = 1.05

  • 4292 reflections

  • 210 parameters

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H3A⋯N2i 0.91 2.43 3.3291 (18) 168
N3—H3B⋯O1ii 0.91 2.03 2.9345 (18) 177
N4—H4A⋯O4 0.91 2.01 2.9212 (16) 174
O4—H4B⋯N2iii 0.84 2.17 3.0032 (19) 172
O4—H4C⋯O2iv 0.84 2.09 2.9122 (18) 168
C4—H4⋯O1 0.95 2.25 2.8484 (17) 121
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) -x+1, -y+2, -z+1; (iii) x, y, z-1; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 1005734

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536814012495/sj5406sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814012495/sj5406Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814012495/sj5406Isup3.cml

checkCIF report


Comment top

A great deal of interest has been focused on the synthesis of functionalized pyridine derivatives due to their biological activities (Shi et al., 2005). For example, some 2-pyridine radicals are incorporated into the structures of cardiotonic agents such as milrinone (Dorigo et al., 1993) and HIV-1 specific transcriptase inhibitors (Dolle et al., 1995). Amino-cyanopyridines have been identified as IKK-β inhibitors (Murata et al., 2003). Many pyridine derivatives are of commercial interest being used as herbicides, fungicides, pesticides, and dyes (Lohray et al., 2004; Merja et al., 2004; Chaki et al., 1995; Thomae et al., 2007). Besides, pyridine derivatives are important and useful intermediates in the preparation of a variety of heterocyclic compounds (Konda et al., 2010). In view of these observations and in continuation of our work on the synthesis of heterocyclic systems for biological evaluations, we report here the synthesis and crystal structure of the title compound.

The title compound (Fig. 1) crystallizes in a "folded" conformation with the ester group lying over the carbamoyl moiety such that the dihedral angle between the best planes through the pyridyl ring and the C11–C13/O3 unit is 22.4 (1)°.

Molecular conformation is stabilized by an intramolecular C—H···O hydrogen bond, forming a S(6) motif, Fig. 1, (Bernstein et al., 1995) and an N—H···O hydrogen bonding interaction involving the lattice water molecule.

This conformation appears to result from the several hydrogen bonding interactions involving the lattice water molecule, Fig. 2 and Table 1. The packing consists of tilted layers running approximately parallel to the c axis, Fig. 3, with the ester groups on the outsides of the layers and having channels running parallel to (101), Fig. 4.

Related literature top

For the synthesis of amino-cyano pyridines, see: Shi et al. (2005). For pyridines as intermediates in the synthesis of different heterocyclic compounds, see: Konda et al. (2010). For the pharmaceutical activity of functionalized pyridine derivatives, see: Dorigo et al. (1993); Dolle et al. (1995); Murata et al. (2003). For industrial applications of pyridine compounds, see: Lohray et al. (2004); Merja et al. (2004); Chaki et al. (1995); Thomae et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a solution of N-[4-amino-5-cyano-6-(methylthio)pyridin-2-yl]-2-chloroacetamide (0.5 g, 1.95 mmol) in 30 ml ethanol and a few drops of triethylamine as a catalyst, ethyl mercaptoacetate (0.23 g, 1.95 mmol) was added. The reaction mixture was refluxed for 3 h at 350 K. The reaction mixture was allowed to cool down and the excess solvent was evaporated under reduced pressure. The precipitate which formed was filtered off, dried under vacuum and recrystallized from ethanol to furnish colourless crystals (yield 0.62 g; 95%). Mp. 423 – 425 K.

IR (νmax, cm-1): 3431, 3335, 3227, (NH2+NH), 2915 (CH aliph.), 2203 (C≡N), 1728 (C=O ester), 1641 (C=O amidic); 1HNMR (DMSO-d6), δ, p.p.m.: 10.34 (s, 1H, NH exchanged by D2O), 7.28 (s, 1H, CH pyridyl), 7.00 (s, 2H, NH2 exchanged by D2O), 4.11- 4.06(q, J = 8 Hz, 2H, CH2), 3.50 (s, 2H, CH2), 3.49 (s, 2H, CH2), 2.53 (s, 3H, CH3), 1.2–1.17 (t, J = 8 Hz, 3H, CH3).

Refinement top

H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to nitrogen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

Structure description top

A great deal of interest has been focused on the synthesis of functionalized pyridine derivatives due to their biological activities (Shi et al., 2005). For example, some 2-pyridine radicals are incorporated into the structures of cardiotonic agents such as milrinone (Dorigo et al., 1993) and HIV-1 specific transcriptase inhibitors (Dolle et al., 1995). Amino-cyanopyridines have been identified as IKK-β inhibitors (Murata et al., 2003). Many pyridine derivatives are of commercial interest being used as herbicides, fungicides, pesticides, and dyes (Lohray et al., 2004; Merja et al., 2004; Chaki et al., 1995; Thomae et al., 2007). Besides, pyridine derivatives are important and useful intermediates in the preparation of a variety of heterocyclic compounds (Konda et al., 2010). In view of these observations and in continuation of our work on the synthesis of heterocyclic systems for biological evaluations, we report here the synthesis and crystal structure of the title compound.

The title compound (Fig. 1) crystallizes in a "folded" conformation with the ester group lying over the carbamoyl moiety such that the dihedral angle between the best planes through the pyridyl ring and the C11–C13/O3 unit is 22.4 (1)°.

Molecular conformation is stabilized by an intramolecular C—H···O hydrogen bond, forming a S(6) motif, Fig. 1, (Bernstein et al., 1995) and an N—H···O hydrogen bonding interaction involving the lattice water molecule.

This conformation appears to result from the several hydrogen bonding interactions involving the lattice water molecule, Fig. 2 and Table 1. The packing consists of tilted layers running approximately parallel to the c axis, Fig. 3, with the ester groups on the outsides of the layers and having channels running parallel to (101), Fig. 4.

For the synthesis of amino-cyano pyridines, see: Shi et al. (2005). For pyridines as intermediates in the synthesis of different heterocyclic compounds, see: Konda et al. (2010). For the pharmaceutical activity of functionalized pyridine derivatives, see: Dorigo et al. (1993); Dolle et al. (1995); Murata et al. (2003). For industrial applications of pyridine compounds, see: Lohray et al. (2004); Merja et al. (2004); Chaki et al. (1995); Thomae et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective view of the asymmetric unit with 50% probability ellipsoids and hydrogen bonds depicted by dashed lines.
[Figure 2] Fig. 2. Packing projected down the b axis showing the inter- and intramolecular hydrogen bonds as dashed lines.
[Figure 3] Fig. 3. Packing projected along the c axis showing the tilted layers.
[Figure 4] Fig. 4. Packing viewed along the axis of the channels. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
Ethyl 2-[({[4-amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]carbamoyl}methyl)sulfanyl]acetate monohydrate top
Crystal data top
C13H16N4O3S2·H2OZ = 2
Mr = 358.45F(000) = 376
Triclinic, P1Dx = 1.442 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0806 (12) ÅCell parameters from 9913 reflections
b = 9.2444 (12) Åθ = 2.4–29.2°
c = 10.7856 (14) ŵ = 0.35 mm−1
α = 101.843 (2)°T = 150 K
β = 100.1750 (19)°Plate, colourless
γ = 105.9480 (19)°0.26 × 0.26 × 0.12 mm
V = 825.48 (19) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer		4292 independent reflections
Graphite monochromator3773 reflections with I > 2σ(I)
Detector resolution: 8.3660 pixels mm-1Rint = 0.034
φ and ω scansθmax = 29.2°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		h = −12→12
Tmin = 0.83, Tmax = 0.96k = −12→12
15313 measured reflectionsl = −14→14
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0515P)2 + 0.3031P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4292 reflectionsΔρmax = 0.44 e Å−3
210 parametersΔρmin = −0.37 e Å−3
Crystal data top
C13H16N4O3S2·H2Oγ = 105.9480 (19)°
Mr = 358.45V = 825.48 (19) Å3
Triclinic, P1Z = 2
a = 9.0806 (12) ÅMo Kα radiation
b = 9.2444 (12) ŵ = 0.35 mm−1
c = 10.7856 (14) ÅT = 150 K
α = 101.843 (2)°0.26 × 0.26 × 0.12 mm
β = 100.1750 (19)°
Data collection top
Bruker SMART APEX CCD
diffractometer		4292 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		3773 reflections with I > 2σ(I)
Tmin = 0.83, Tmax = 0.96Rint = 0.034
15313 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.05Δρmax = 0.44 e Å−3
4292 reflectionsΔρmin = −0.37 e Å−3
210 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S11.14877 (5)0.74276 (5)0.62470 (3)0.0316 (1)
S20.40426 (4)0.82259 (4)0.00905 (3)0.0218 (1)
O10.50975 (12)0.88281 (13)0.30154 (9)0.0263 (3)
O20.16728 (13)0.58384 (14)0.15365 (11)0.0325 (3)
O30.38626 (12)0.51837 (12)0.14447 (9)0.0244 (3)
N10.91851 (13)0.79013 (14)0.46377 (11)0.0200 (3)
N21.05234 (16)0.87115 (18)0.92745 (12)0.0330 (4)
N30.73517 (14)0.97498 (15)0.76432 (11)0.0257 (3)
N40.73715 (13)0.82181 (14)0.30697 (10)0.0204 (3)
C10.98222 (15)0.80180 (16)0.58659 (13)0.0193 (3)
C20.92486 (15)0.86183 (16)0.69216 (12)0.0192 (3)
C30.79351 (15)0.91523 (16)0.66734 (12)0.0194 (3)
C40.72390 (15)0.89929 (16)0.53540 (12)0.0207 (4)
C50.79125 (15)0.83911 (15)0.44086 (12)0.0185 (3)
C61.1786 (2)0.6781 (3)0.46517 (17)0.0480 (7)
C70.99695 (16)0.86718 (17)0.82188 (13)0.0225 (4)
C80.60550 (15)0.84739 (16)0.24588 (12)0.0194 (3)
C90.59280 (16)0.82956 (17)0.10018 (13)0.0215 (4)
C100.28999 (17)0.61849 (17)−0.02404 (13)0.0247 (4)
C110.27024 (16)0.57242 (17)0.09924 (13)0.0237 (4)
C120.3870 (2)0.4842 (2)0.27094 (15)0.0315 (5)
C130.5180 (2)0.4186 (2)0.30413 (16)0.0335 (5)
O40.91965 (12)0.72768 (13)0.12641 (10)0.0287 (3)
H3A0.793201.001600.848300.0310*
H3B0.656601.016100.744500.0310*
H40.632900.929300.512400.0250*
H4A0.799700.794500.255500.0240*
H6A1.084600.592400.410900.0720*
H6B1.270600.641700.473000.0720*
H6C1.196800.765000.424600.0720*
H9A0.614100.732500.062700.0260*
H9B0.675600.918200.089600.0260*
H10A0.184500.59830−0.081400.0300*
H10B0.343500.55330−0.071200.0300*
H12A0.284300.407700.266700.0380*
H12B0.403300.580800.339100.0380*
H13A0.504700.326900.233400.0500*
H13B0.515200.388100.385700.0500*
H13C0.619900.497900.314900.0500*
H4B0.949800.772800.070900.0340*
H4C0.992200.690300.146300.0340*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0310 (2)0.0527 (3)0.0213 (2)0.0314 (2)0.0049 (1)0.0089 (2)
S20.0225 (2)0.0265 (2)0.0184 (2)0.0128 (1)0.0009 (1)0.0072 (1)
O10.0212 (5)0.0418 (6)0.0196 (5)0.0182 (4)0.0036 (4)0.0063 (4)
O20.0282 (5)0.0444 (7)0.0334 (6)0.0193 (5)0.0132 (5)0.0134 (5)
O30.0255 (5)0.0313 (5)0.0225 (5)0.0142 (4)0.0094 (4)0.0108 (4)
N10.0184 (5)0.0261 (6)0.0182 (5)0.0121 (4)0.0041 (4)0.0054 (4)
N20.0328 (7)0.0520 (9)0.0211 (6)0.0253 (6)0.0055 (5)0.0097 (6)
N30.0227 (6)0.0408 (7)0.0167 (5)0.0186 (5)0.0037 (4)0.0041 (5)
N40.0185 (5)0.0299 (6)0.0156 (5)0.0132 (5)0.0038 (4)0.0053 (4)
C10.0171 (6)0.0242 (6)0.0188 (6)0.0111 (5)0.0032 (5)0.0055 (5)
C20.0168 (6)0.0253 (6)0.0167 (6)0.0098 (5)0.0024 (4)0.0054 (5)
C30.0159 (6)0.0238 (6)0.0180 (6)0.0075 (5)0.0030 (4)0.0039 (5)
C40.0175 (6)0.0281 (7)0.0179 (6)0.0119 (5)0.0022 (5)0.0047 (5)
C50.0158 (5)0.0225 (6)0.0168 (6)0.0078 (5)0.0010 (4)0.0046 (5)
C60.0526 (11)0.0851 (15)0.0276 (8)0.0544 (11)0.0149 (7)0.0128 (9)
C70.0190 (6)0.0314 (7)0.0202 (6)0.0135 (5)0.0053 (5)0.0056 (5)
C80.0180 (6)0.0226 (6)0.0178 (6)0.0088 (5)0.0022 (4)0.0050 (5)
C90.0190 (6)0.0309 (7)0.0190 (6)0.0128 (5)0.0047 (5)0.0097 (5)
C100.0264 (7)0.0266 (7)0.0197 (6)0.0094 (6)0.0026 (5)0.0045 (5)
C110.0223 (6)0.0249 (7)0.0235 (6)0.0087 (5)0.0043 (5)0.0053 (5)
C120.0360 (8)0.0431 (9)0.0269 (7)0.0198 (7)0.0151 (6)0.0184 (7)
C130.0391 (9)0.0396 (9)0.0301 (8)0.0198 (7)0.0100 (6)0.0161 (7)
O40.0258 (5)0.0376 (6)0.0301 (5)0.0171 (5)0.0113 (4)0.0116 (5)
Geometric parameters (Å, º) top
S1—C11.7550 (15)C2—C31.415 (2)
S1—C61.7952 (18)C2—C71.4208 (19)
S2—C91.7945 (15)C3—C41.4111 (18)
S2—C101.8113 (16)C4—C51.3776 (19)
O1—C81.2181 (18)C8—C91.5262 (18)
O2—C111.2051 (19)C10—C111.502 (2)
O3—C111.3436 (19)C12—C131.499 (3)
O3—C121.4613 (19)C4—H40.9500
O4—H4C0.8400C6—H6B0.9800
O4—H4B0.8400C6—H6A0.9800
N1—C11.3181 (18)C6—H6C0.9800
N1—C51.3543 (19)C9—H9B0.9900
N2—C71.1494 (19)C9—H9A0.9900
N3—C31.3414 (18)C10—H10B0.9900
N4—C51.4013 (16)C10—H10A0.9900
N4—C81.3639 (19)C12—H12B0.9900
N3—H3A0.9100C12—H12A0.9900
N3—H3B0.9100C13—H13C0.9800
N4—H4A0.9100C13—H13A0.9800
C1—C21.4088 (19)C13—H13B0.9800
C1—S1—C6101.26 (8)O2—C11—C10125.82 (14)
C9—S2—C10101.89 (7)O3—C12—C13108.59 (14)
C11—O3—C12115.32 (12)C5—C4—H4121.00
H4B—O4—H4C102.00C3—C4—H4121.00
C1—N1—C5116.87 (12)S1—C6—H6A109.00
C5—N4—C8127.62 (12)S1—C6—H6B109.00
H3A—N3—H3B120.00H6A—C6—H6B110.00
C3—N3—H3B119.00H6A—C6—H6C109.00
C3—N3—H3A119.00S1—C6—H6C109.00
C5—N4—H4A116.00H6B—C6—H6C109.00
C8—N4—H4A116.00S2—C9—H9B109.00
S1—C1—N1119.69 (11)C8—C9—H9A109.00
S1—C1—C2116.86 (10)S2—C9—H9A109.00
N1—C1—C2123.45 (13)H9A—C9—H9B108.00
C1—C2—C3119.22 (12)C8—C9—H9B109.00
C1—C2—C7120.40 (13)S2—C10—H10A109.00
C3—C2—C7120.38 (12)C11—C10—H10A109.00
N3—C3—C4121.32 (13)C11—C10—H10B109.00
N3—C3—C2121.69 (12)H10A—C10—H10B108.00
C2—C3—C4116.98 (12)S2—C10—H10B109.00
C3—C4—C5118.29 (13)O3—C12—H12A110.00
N1—C5—N4110.75 (11)C13—C12—H12A110.00
N4—C5—C4124.09 (13)C13—C12—H12B110.00
N1—C5—C4125.16 (12)O3—C12—H12B110.00
N2—C7—C2178.60 (17)H12A—C12—H12B108.00
O1—C8—C9123.62 (13)C12—C13—H13B110.00
O1—C8—N4123.88 (12)C12—C13—H13C109.00
N4—C8—C9112.49 (12)C12—C13—H13A109.00
S2—C9—C8114.23 (10)H13A—C13—H13C109.00
S2—C10—C11111.95 (10)H13B—C13—H13C109.00
O3—C11—C10110.84 (12)H13A—C13—H13B109.00
O2—C11—O3123.32 (13)
C6—S1—C1—N1−0.35 (15)S1—C1—C2—C7−2.41 (19)
C6—S1—C1—C2−179.63 (14)N1—C1—C2—C3−1.0 (2)
C10—S2—C9—C8−83.84 (12)N1—C1—C2—C7178.34 (14)
C9—S2—C10—C1163.79 (12)C1—C2—C3—N3−179.28 (14)
C12—O3—C11—O2−4.3 (2)C1—C2—C3—C42.2 (2)
C12—O3—C11—C10174.39 (12)C7—C2—C3—N31.4 (2)
C11—O3—C12—C13177.43 (13)C7—C2—C3—C4−177.10 (14)
C5—N1—C1—S1−179.33 (11)N3—C3—C4—C5179.07 (14)
C5—N1—C1—C2−0.1 (2)C2—C3—C4—C5−2.4 (2)
C1—N1—C5—N4179.28 (13)C3—C4—C5—N11.5 (2)
C1—N1—C5—C4−0.2 (2)C3—C4—C5—N4−177.88 (13)
C8—N4—C5—N1174.69 (14)O1—C8—C9—S2−13.0 (2)
C8—N4—C5—C4−5.9 (2)N4—C8—C9—S2168.00 (10)
C5—N4—C8—O1−3.9 (2)S2—C10—C11—O286.96 (18)
C5—N4—C8—C9175.09 (13)S2—C10—C11—O3−91.73 (13)
S1—C1—C2—C3178.25 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N2i0.912.433.3291 (18)168
N3—H3B···O1ii0.912.032.9345 (18)177
N4—H4A···O40.912.012.9212 (16)174
O4—H4B···N2iii0.842.173.0032 (19)172
O4—H4C···O2iv0.842.092.9122 (18)168
C4—H4···O10.952.252.8484 (17)121
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+2, −z+1; (iii) x, y, z−1; (iv) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N2i0.912.433.3291 (18)168
N3—H3B···O1ii0.912.032.9345 (18)177
N4—H4A···O40.912.012.9212 (16)174
O4—H4B···N2iii0.842.173.0032 (19)172
O4—H4C···O2iv0.842.092.9122 (18)168
C4—H4···O10.952.252.8484 (17)121
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+2, −z+1; (iii) x, y, z−1; (iv) x+1, y, z.
 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

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ISSN: 2056-9890
Volume 70| Part 7| July 2014| Pages o745-o746
https://doi.org/10.1107/S1600536814012495
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