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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 2| Part 9| September 2017| x171258
https://doi.org/10.1107/S2414314617012585

2,3-Bis(benzyl­thio)-6-methyl­quinoxaline

CROSSMARK_Color_square_no_text.svg
Ayman Zouitini,a* Youssef Kandri Rodi,a Younes Ouzidan,a* Jerry P. Jasinski,b Manpreet Kaurb and El Mokhtar Essassic

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH, 03435-2001, USA, and cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences, Pharmacochimie, Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat, Morocco
*Correspondence e-mail: ayman.zouitini@gmail.com, younes.ouzidan@usmba.ac.ma

Edited by A. J. Lough, University of Toronto, Canada (Received 8 August 2017; accepted 1 September 2017; online 8 September 2017)

In the title compound, C23H20N2S2, the mean planes of the phenyl rings are twisted with respect to the mean plane of the quinoxaline ring system by 73.8 (8) and 72.2 (8)°. A weak intra­molecular C—H⋯N inter­actions is observed. The methyl group attached to the quinoxaline ring system is disordered over two sets of sites on the benzene ring having occupancies 0.531 (7) and 0.469 (7), respectively. One of the phenyl rings is disordered over two sets of sites having occupancies 0.649 (7) and 0.351 (10), respectively. In the crystal, π–π stacking inter­actions occur.

CCDC reference: 1572194

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Quinoxalines exhibit various biological activities including anti­viral (Fonseca et al., 2004[Fonseca, T., Gigante, B., Marques, M. M., Gilchrist, T. L. De & De Clercq, E. (2004). Bioorg. Med. Chem. 12, 103-112.]), anti­bacterial (El-Sabbagh et al., 2009[El-Sabbagh, O. I., El-Sadek, M. E., Lashine, S. M., Yassin, S. H. & El-Nabtity, S. M. (2009). Med. Chem. Res. 18, 782-797.]), anti-inflammatory (Wagle et al., 2008[Wagle, S., Adhikari, A. V. & Kumari, N. S. (2008). Ind. J. Chem. 47, 439-448.]), anti­protozoal (Hui et al., 2006[Hui, X., Desrivot, J., Bories, C., Loiseau, P. M., Franck, X., Hocquemiller, R. & Figadère, B. (2006). Bioorg. Med. Chem. Lett. 16, 815-820.]), anti­cancer (Carta et al., 2006[Carta, A., Loriga, M., Piras, S., Paglietti, G., La Colla, P., Busonera, B., Collu, G. & Loddo, R. (2006). Med. Chem. 2, 113-122.]) and anti­tuberculosis (Ancizu et al., 2010[Ancizu, S., Moreno, E., Solano, B., Villar, R., Burguete, A., Torres, E., Pérez-Silanes, S., Aldana, I. & Monge, A. (2010). Bioorg. Med. Chem. 18, 2713-2719.]) activities. Additionally, they are used in the agricultural field as fungicides, herbicides and insecticides (Kurasawa et al., 1988[Kurasawa, Y., Sakata, G. & Makino, K. (1988). Heterocycles, 27, 2481-2515.]). Quinoxaline moieties are also present in the structures of various anti­biotics such as echinomycin, levomycin, and actinoleutin, which are known to inhibit the growth of gram-positive bacteria and are active against various transplantable tumors (Kim et al., 2004[Kim, Y. B., Kim, Y. H., Park, J. Y. & Kim, S. K. (2004). Bioorg. Med. Chem. Lett. 14, 541-544.]). In this work, we report the synthesis and structure of the title compound.

The mol­ecular structure of the title compound is shown in Fig. 1[link]. The mean planes of the pendant phenyl rings of the benzyl­thio groups are twisted with respect to the mean plane of the quinoxaline ring system by 73.8 (8)° (C17–C22) and 72.2 (8)° (C10–C15). The benzyl­thio moieties are attached to the ring in adjacent locations [S—C—C—S = −2.2 (2)°], avoiding steric repulsion. An intramolecular C—H⋯N hydrogen bond occurs. (Table 1[link]). The crystal packing (Fig. 2[link]) features weak π–π stacking inter­actions involving the quinoxaline moiety [inter­centroid distance, Cg1⋯Cg2ii = 3.7254 (13), Cg1⋯Cg3ii = 3.7254 (13) Å; symmetry code: (ii) = 1 − x, 1 − y, 1 − z; Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C2/N2/C3/C4, C3–C8 and C3/C4/C5/C6A/C7A/C8 rings, respectively].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C15—H15⋯N1 0.93 2.73 3.348 (5) 125
[Figure 1]
Figure 1
The mol­ecular structure of the title compound showing 30% probability displacement ellipsoids. Atom C23, [0.531 (7) occupancy] methyl group is shown bonded to C7, whereas minor occupancy atom C23A, [0.469 (7) occupancy] has been omitted for clarity. Only atoms C9—C15 [occupancy 0.649 (7)] of the disordered phenyl ring of the the benzyl­thio ring system are shown for clarity.
[Figure 2]
Figure 2
Packing of the title compound viewed along the b axis. The weak C15—H15⋯N1 intra­molecular inter­actions (Table 1[link]) are drawn as dashed lines. Hydrogen atoms not involved in the packing are removed for clarity.

Synthesis and crystallization

To a solution of 6-methyl-1,4-di­hydro­quinoxaline-2,3-di­thione 0.3 g (1.44 mmol) in DMF (20 ml), were added 0.47 g (3.61 mmol) of potassium carbonate and 0.1 mmol of tetra-n-butyl ammonium bromide (TBAB). After stirring for 10 min, 0.4 ml (3.46 mmol) of benzyl chloride was added, then the mixture was allowed to stir at room temperature for 12 h. After filtration, DMF was evaporated under reduced pressure and the residue obtained was dissolved in di­chloro­methane. The organic phase was then dried over Na2SO4 and concentrated. The mixture obtained was chromatographed on a silica gel column [eluent: hexa­ne/ethyl acetate (3/1)]. The compound formed pale-yellow columnar crystals in 30% yield and was recrystallized from a solvent mixture (ethyl acetate–hexa­ne: 1/3).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The methyl group is disordered each over atomic sites on C6 and C7 of the quinoxaline ring [occupancies C23: 0.531 (7) and C23A: 0.469 (7)]. Idealized disordered Me groups were refined as rotating groups. The phenyl ring on one of the benzyl­thio moieties (C9–C15) is disordered over two sets of atomic sites having occupancies 0.649 (7) and 0.351 (10).

Table 2
Experimental details

Crystal data
Chemical formula C23H20N2S2
Mr 388.53
Crystal system, space group Monoclinic, C2/c
Temperature (K) 293
a, b, c (Å) 22.5053 (6), 7.3510 (2), 26.1729 (7)
β (°) 109.146 (3)
V (Å3) 4090.4 (2)
Z 8
Radiation type Cu Kα
μ (mm−1) 2.42
Crystal size (mm) 0.4 × 0.14 × 0.06
 
Data collection
Diffractometer Rigaku, Oxford diffraction
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, The Woodlands, Texas, USA.])
Tmin, Tmax 0.664, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 7343, 3878, 3252
Rint 0.016
(sin θ/λ)max (Å−1) 0.614
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.168, 1.08
No. of reflections 3878
No. of parameters 296
No. of restraints 216
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.52, −0.27
Computer programs: CrysAlis PRO (Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, The Woodlands, Texas, USA.]), SHELXT (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), SHELXL (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data

CCDC reference: 1572194

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617012585/lh4022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617012585/lh4022Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617012585/lh4022Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314617012585/lh4022Isup4.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(I) top
Crystal data top
C23H20N2S2F(000) = 1632
Mr = 388.53Dx = 1.262 Mg m−3
Monoclinic, C2/cCu Kα radiation, λ = 1.54184 Å
a = 22.5053 (6) ÅCell parameters from 3411 reflections
b = 7.3510 (2) Åθ = 4.2–71.4°
c = 26.1729 (7) ŵ = 2.42 mm−1
β = 109.146 (3)°T = 293 K
V = 4090.4 (2) Å3Plate, colourless
Z = 80.4 × 0.14 × 0.06 mm
Data collection top
Rigaku, Oxford diffraction
diffractometer		3878 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source3252 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 16.0416 pixels mm-1θmax = 71.3°, θmin = 3.6°
ω scansh = −27→25
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)		k = −8→5
Tmin = 0.664, Tmax = 1.000l = −32→31
7343 measured reflections
Refinement top
Refinement on F2216 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.168 w = 1/[σ2(Fo2) + (0.0962P)2 + 2.177P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3878 reflectionsΔρmax = 0.52 e Å−3
296 parametersΔρmin = −0.27 e Å−3
Special details top

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

Refinement. All H atoms were placed in calculated positions and refined using the riding model with C—H bond lengths of 0.93 Å (CH), 0.97 Å (CH2) or 0.96 Å (CH3). Isotropic displacement parameters were set to 1.2 (CH) or 1.5 (CH3) times Ueq of the parent atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.33518 (3)0.82695 (9)0.39063 (3)0.0642 (2)
S20.33006 (3)0.70876 (9)0.50202 (3)0.0626 (2)
N10.46013 (10)0.8150 (2)0.43418 (8)0.0520 (4)
N20.45531 (10)0.6941 (3)0.53453 (8)0.0530 (5)
C10.40706 (11)0.7898 (3)0.44286 (9)0.0501 (5)
C20.40456 (11)0.7310 (3)0.49446 (9)0.0501 (5)
C30.51165 (11)0.7182 (3)0.52615 (9)0.0500 (5)
C40.51428 (11)0.7804 (3)0.47631 (9)0.0507 (5)
C50.57320 (12)0.8071 (3)0.46956 (11)0.0591 (6)
H5A0.57520.84980.43670.071*0.531 (7)
H5B0.57520.84980.43670.071*0.469 (7)
C60.62759 (13)0.7707 (3)0.51099 (12)0.0645 (6)0.531 (7)
H60.66630.78640.50600.077*0.531 (7)
C6A0.62759 (13)0.7707 (3)0.51099 (12)0.0645 (6)0.469 (7)
C70.62480 (13)0.7098 (4)0.56094 (12)0.0650 (7)0.531 (7)
C7A0.62480 (13)0.7098 (4)0.56094 (12)0.0650 (7)0.469 (7)
H7A0.66180.68740.58920.078*0.469 (7)
C80.56820 (13)0.6831 (3)0.56825 (10)0.0600 (6)
H8A0.56690.64120.60140.072*0.531 (7)
H8B0.56690.64120.60140.072*0.469 (7)
C90.3589 (7)0.875 (3)0.3360 (6)0.066 (3)0.649 (10)
H9A0.32760.95420.31210.080*0.649 (10)
H9B0.39770.94380.34910.080*0.649 (10)
C9A0.3660 (14)0.879 (5)0.3300 (11)0.057 (2)0.351 (10)
H9AA0.33690.95710.30350.068*0.351 (10)
H9AB0.40690.93710.34260.068*0.351 (10)
C100.3703 (2)0.7144 (5)0.3010 (2)0.0628 (12)0.649 (10)
C110.31740 (19)0.6550 (7)0.2597 (2)0.0774 (13)0.649 (10)
H110.27960.71750.25220.093*0.649 (10)
C120.3211 (2)0.5021 (8)0.2296 (2)0.0916 (16)0.649 (10)
H120.28570.46240.20200.110*0.649 (10)
C130.3776 (3)0.4087 (5)0.2409 (2)0.0944 (16)0.649 (10)
H130.38000.30640.22070.113*0.649 (10)
C140.4305 (3)0.4681 (7)0.2822 (2)0.0813 (15)0.649 (10)
H140.46830.40560.28970.098*0.649 (10)
C150.4268 (2)0.6209 (8)0.3123 (2)0.0682 (13)0.649 (10)
H150.46220.66070.33990.082*0.649 (10)
C10A0.3697 (5)0.7061 (11)0.3080 (4)0.0661 (19)0.351 (10)
C11A0.3235 (4)0.5893 (15)0.2767 (4)0.089 (2)0.351 (10)
H11A0.28140.61260.27170.107*0.351 (10)
C12A0.3403 (5)0.4376 (14)0.2528 (5)0.099 (2)0.351 (10)
H12A0.30940.35950.23180.119*0.351 (10)
C13A0.4033 (5)0.4028 (10)0.2602 (4)0.089 (2)0.351 (10)
H13A0.41450.30140.24420.107*0.351 (10)
C14A0.4495 (4)0.5197 (15)0.2916 (4)0.081 (2)0.351 (10)
H14A0.49160.49640.29650.097*0.351 (10)
C15A0.4327 (4)0.6713 (14)0.3155 (5)0.072 (2)0.351 (10)
H15A0.46360.74940.33640.087*0.351 (10)
C160.35130 (15)0.6469 (4)0.57315 (11)0.0703 (7)
H16A0.31540.58960.57920.084*
H16B0.38500.55810.58150.084*
C170.37198 (13)0.8046 (4)0.61114 (10)0.0647 (7)
C180.32859 (17)0.9235 (6)0.61799 (15)0.0986 (12)
H180.28610.90710.59880.118*
C190.3477 (2)1.0682 (8)0.65341 (19)0.1274 (17)
H190.31801.14900.65800.153*
C200.4105 (2)1.0931 (6)0.68195 (15)0.1080 (13)
H200.42331.19060.70560.130*
C210.45277 (18)0.9760 (6)0.67534 (11)0.0920 (11)
H210.49520.99160.69490.110*
C220.43439 (14)0.8333 (5)0.64014 (10)0.0750 (8)
H220.46460.75430.63570.090*
C230.6846 (3)0.6864 (8)0.6061 (3)0.082 (2)0.531 (7)
H23A0.67590.67090.63930.123*0.531 (7)
H23B0.71050.79210.60860.123*0.531 (7)
H23C0.70630.58110.59950.123*0.531 (7)
C23A0.6940 (3)0.7870 (8)0.5048 (3)0.075 (2)0.469 (7)
H23D0.68960.82230.46840.113*0.469 (7)
H23E0.71510.67170.51260.113*0.469 (7)
H23F0.71820.87700.52950.113*0.469 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0589 (4)0.0719 (4)0.0572 (4)0.0040 (3)0.0126 (3)−0.0033 (3)
S20.0587 (4)0.0703 (4)0.0619 (4)−0.0067 (3)0.0241 (3)−0.0106 (3)
N10.0593 (11)0.0463 (10)0.0498 (10)−0.0027 (8)0.0172 (8)−0.0023 (7)
N20.0626 (11)0.0471 (10)0.0507 (10)−0.0011 (8)0.0206 (9)−0.0025 (7)
C10.0569 (12)0.0405 (11)0.0504 (11)−0.0016 (9)0.0142 (9)−0.0087 (8)
C20.0567 (12)0.0419 (11)0.0530 (11)−0.0017 (9)0.0199 (10)−0.0084 (9)
C30.0579 (12)0.0395 (10)0.0519 (11)0.0010 (9)0.0171 (10)−0.0047 (8)
C40.0593 (13)0.0396 (11)0.0528 (11)−0.0034 (9)0.0177 (10)−0.0059 (8)
C50.0632 (14)0.0512 (13)0.0658 (14)−0.0068 (10)0.0251 (11)−0.0022 (10)
C60.0587 (14)0.0511 (13)0.0826 (17)−0.0063 (11)0.0218 (13)−0.0076 (12)
C6A0.0587 (14)0.0511 (13)0.0826 (17)−0.0063 (11)0.0218 (13)−0.0076 (12)
C70.0579 (14)0.0538 (14)0.0730 (16)0.0044 (11)0.0075 (12)−0.0039 (11)
C7A0.0579 (14)0.0538 (14)0.0730 (16)0.0044 (11)0.0075 (12)−0.0039 (11)
C80.0665 (15)0.0514 (13)0.0570 (13)0.0018 (11)0.0135 (11)−0.0009 (10)
C90.069 (4)0.067 (3)0.058 (5)0.006 (3)0.013 (3)0.004 (4)
C9A0.066 (5)0.070 (4)0.041 (4)−0.002 (4)0.027 (3)0.014 (3)
C100.069 (2)0.074 (2)0.051 (2)0.000 (2)0.0270 (18)0.0056 (18)
C110.073 (2)0.099 (3)0.065 (3)−0.008 (2)0.028 (2)−0.006 (2)
C120.094 (3)0.112 (4)0.069 (3)−0.018 (3)0.026 (2)−0.021 (3)
C130.112 (4)0.105 (3)0.070 (3)0.003 (3)0.035 (3)−0.018 (3)
C140.096 (3)0.091 (3)0.057 (3)0.015 (3)0.026 (3)−0.002 (3)
C150.078 (3)0.076 (3)0.051 (2)0.014 (2)0.0222 (19)0.010 (2)
C10A0.070 (3)0.078 (3)0.052 (3)0.000 (3)0.022 (3)0.008 (3)
C11A0.083 (4)0.097 (4)0.083 (4)−0.007 (4)0.021 (4)−0.009 (4)
C12A0.101 (4)0.104 (4)0.085 (4)−0.002 (4)0.021 (4)−0.020 (4)
C13A0.100 (5)0.097 (4)0.069 (5)0.006 (4)0.025 (4)−0.019 (4)
C14A0.098 (4)0.087 (4)0.061 (4)0.003 (4)0.031 (4)−0.003 (4)
C15A0.087 (4)0.076 (4)0.056 (3)0.008 (3)0.028 (3)0.014 (3)
C160.0798 (17)0.0707 (16)0.0676 (15)−0.0162 (14)0.0339 (13)0.0022 (13)
C170.0684 (15)0.0785 (17)0.0527 (13)−0.0109 (13)0.0275 (12)0.0012 (11)
C180.0750 (19)0.133 (3)0.089 (2)−0.010 (2)0.0285 (17)−0.039 (2)
C190.114 (3)0.150 (4)0.116 (3)0.011 (3)0.034 (3)−0.063 (3)
C200.128 (3)0.119 (3)0.0693 (19)−0.026 (3)0.022 (2)−0.035 (2)
C210.091 (2)0.133 (3)0.0492 (14)−0.027 (2)0.0189 (14)−0.0104 (17)
C220.0727 (17)0.104 (2)0.0478 (13)−0.0045 (15)0.0195 (12)0.0048 (13)
C230.055 (3)0.064 (3)0.105 (5)0.016 (2)−0.003 (3)−0.006 (3)
C23A0.062 (3)0.055 (3)0.105 (5)−0.006 (2)0.023 (3)0.001 (3)
Geometric parameters (Å, º) top
S1—C11.763 (2)C12—C131.3900
S1—C91.719 (14)C13—H130.9300
S1—C9A1.97 (2)C13—C141.3900
S2—C21.759 (2)C14—H140.9300
S2—C161.821 (3)C14—C151.3900
N1—C11.300 (3)C15—H150.9300
N1—C41.373 (3)C10A—C11A1.3900
N2—C21.301 (3)C10A—C15A1.3900
N2—C31.367 (3)C11A—H11A0.9300
C1—C21.437 (3)C11A—C12A1.3900
C3—C41.402 (3)C12A—H12A0.9300
C3—C81.407 (3)C12A—C13A1.3900
C4—C51.408 (3)C13A—H13A0.9300
C5—H5A0.9300C13A—C14A1.3900
C5—H5B0.9300C14A—H14A0.9300
C5—C61.369 (4)C14A—C15A1.3900
C5—C6A1.369 (4)C15A—H15A0.9300
C6—H60.9300C16—H16A0.9700
C6—C71.403 (4)C16—H16B0.9700
C6A—C7A1.403 (4)C16—C171.499 (4)
C6A—C23A1.560 (7)C17—C181.365 (5)
C7—C81.363 (4)C17—C221.376 (4)
C7—C231.482 (6)C18—H180.9300
C7A—H7A0.9300C18—C191.384 (6)
C7A—C81.363 (4)C19—H190.9300
C8—H8A0.9300C19—C201.377 (6)
C8—H8B0.9300C20—H200.9300
C9—H9A0.9700C20—C211.336 (6)
C9—H9B0.9700C21—H210.9300
C9—C101.563 (19)C21—C221.367 (5)
C9A—H9AA0.9700C22—H220.9300
C9A—H9AB0.9700C23—H23A0.9600
C9A—C10A1.41 (4)C23—H23B0.9600
C10—C111.3900C23—H23C0.9600
C10—C151.3900C23A—H23D0.9600
C11—H110.9300C23A—H23E0.9600
C11—C121.3900C23A—H23F0.9600
C12—H120.9300
C1—S1—C9A100.3 (9)C12—C13—C14120.0
C9—S1—C1102.7 (5)C14—C13—H13120.0
C2—S2—C16101.41 (13)C13—C14—H14120.0
C1—N1—C4117.2 (2)C15—C14—C13120.0
C2—N2—C3117.3 (2)C15—C14—H14120.0
N1—C1—S1120.29 (18)C10—C15—H15120.0
N1—C1—C2121.9 (2)C14—C15—C10120.0
C2—C1—S1117.81 (18)C14—C15—H15120.0
N2—C2—S2120.46 (18)C11A—C10A—C9A131.7 (14)
N2—C2—C1121.7 (2)C11A—C10A—C15A120.0
C1—C2—S2117.79 (18)C15A—C10A—C9A107.7 (14)
N2—C3—C4121.1 (2)C10A—C11A—H11A120.0
N2—C3—C8119.9 (2)C10A—C11A—C12A120.0
C4—C3—C8119.0 (2)C12A—C11A—H11A120.0
N1—C4—C3120.7 (2)C11A—C12A—H12A120.0
N1—C4—C5119.9 (2)C13A—C12A—C11A120.0
C3—C4—C5119.4 (2)C13A—C12A—H12A120.0
C4—C5—H5A119.7C12A—C13A—H13A120.0
C4—C5—H5B119.7C12A—C13A—C14A120.0
C6—C5—C4120.5 (2)C14A—C13A—H13A120.0
C6—C5—H5A119.7C13A—C14A—H14A120.0
C6A—C5—C4120.5 (2)C15A—C14A—C13A120.0
C6A—C5—H5B119.7C15A—C14A—H14A120.0
C5—C6—H6120.0C10A—C15A—H15A120.0
C5—C6—C7119.9 (3)C14A—C15A—C10A120.0
C7—C6—H6120.0C14A—C15A—H15A120.0
C5—C6A—C7A119.9 (3)S2—C16—H16A108.8
C5—C6A—C23A122.7 (4)S2—C16—H16B108.8
C7A—C6A—C23A117.3 (4)H16A—C16—H16B107.7
C6—C7—C23118.3 (4)C17—C16—S2113.9 (2)
C8—C7—C6120.4 (2)C17—C16—H16A108.8
C8—C7—C23121.2 (4)C17—C16—H16B108.8
C6A—C7A—H7A119.8C18—C17—C16120.2 (3)
C8—C7A—C6A120.4 (2)C18—C17—C22118.3 (3)
C8—C7A—H7A119.8C22—C17—C16121.6 (3)
C3—C8—H8A119.7C17—C18—H18119.9
C3—C8—H8B119.7C17—C18—C19120.1 (4)
C7—C8—C3120.7 (2)C19—C18—H18119.9
C7—C8—H8A119.7C18—C19—H19119.9
C7A—C8—C3120.7 (2)C20—C19—C18120.2 (4)
C7A—C8—H8B119.7C20—C19—H19119.9
S1—C9—H9A107.5C19—C20—H20120.3
S1—C9—H9B107.5C21—C20—C19119.5 (4)
H9A—C9—H9B107.0C21—C20—H20120.3
C10—C9—S1119.2 (12)C20—C21—H21119.7
C10—C9—H9A107.5C20—C21—C22120.7 (3)
C10—C9—H9B107.5C22—C21—H21119.7
S1—C9A—H9AA111.0C17—C22—H22119.4
S1—C9A—H9AB111.0C21—C22—C17121.2 (3)
H9AA—C9A—H9AB109.0C21—C22—H22119.4
C10A—C9A—S1103.8 (18)C7—C23—H23A109.5
C10A—C9A—H9AA111.0C7—C23—H23B109.5
C10A—C9A—H9AB111.0C7—C23—H23C109.5
C11—C10—C9115.4 (7)H23A—C23—H23B109.5
C11—C10—C15120.0H23A—C23—H23C109.5
C15—C10—C9124.3 (7)H23B—C23—H23C109.5
C10—C11—H11120.0C6A—C23A—H23D109.5
C10—C11—C12120.0C6A—C23A—H23E109.5
C12—C11—H11120.0C6A—C23A—H23F109.5
C11—C12—H12120.0H23D—C23A—H23E109.5
C13—C12—C11120.0H23D—C23A—H23F109.5
C13—C12—H12120.0H23E—C23A—H23F109.5
C12—C13—H13120.0
S1—C1—C2—S2−2.2 (2)C6—C7—C8—C3−0.8 (4)
S1—C1—C2—N2177.44 (17)C6A—C7A—C8—C3−0.8 (4)
S1—C9—C10—C1186.6 (11)C8—C3—C4—N1179.6 (2)
S1—C9—C10—C15−86.9 (11)C8—C3—C4—C5−0.3 (3)
S1—C9A—C10A—C11A74 (2)C9—S1—C1—N14.8 (7)
S1—C9A—C10A—C15A−115.1 (12)C9—S1—C1—C2−175.0 (7)
S2—C16—C17—C1876.2 (3)C9—C10—C11—C12−173.8 (8)
S2—C16—C17—C22−104.2 (3)C9—C10—C15—C14173.2 (8)
N1—C1—C2—S2177.94 (16)C9A—S1—C1—N15.1 (12)
N1—C1—C2—N2−2.4 (3)C9A—S1—C1—C2−174.7 (12)
N1—C4—C5—C6−179.1 (2)C9A—C10A—C11A—C12A169.6 (18)
N1—C4—C5—C6A−179.1 (2)C9A—C10A—C15A—C14A−171.9 (14)
N2—C3—C4—N1−1.4 (3)C10—C11—C12—C130.0
N2—C3—C4—C5178.71 (19)C11—C10—C15—C140.0
N2—C3—C8—C7−178.7 (2)C11—C12—C13—C140.0
N2—C3—C8—C7A−178.7 (2)C12—C13—C14—C150.0
C1—S1—C9—C1086.3 (10)C13—C14—C15—C100.0
C1—N1—C4—C30.8 (3)C15—C10—C11—C120.0
C1—N1—C4—C5−179.3 (2)C10A—C11A—C12A—C13A0.0
C2—S2—C16—C1778.6 (2)C11A—C10A—C15A—C14A0.0
C2—N2—C3—C40.1 (3)C11A—C12A—C13A—C14A0.0
C2—N2—C3—C8179.1 (2)C12A—C13A—C14A—C15A0.0
C3—N2—C2—S2−178.60 (15)C13A—C14A—C15A—C10A0.0
C3—N2—C2—C11.7 (3)C15A—C10A—C11A—C12A0.0
C3—C4—C5—C60.8 (4)C16—S2—C2—N23.6 (2)
C3—C4—C5—C6A0.8 (4)C16—S2—C2—C1−176.71 (18)
C4—N1—C1—S1−178.86 (15)C16—C17—C18—C19179.5 (4)
C4—N1—C1—C21.0 (3)C16—C17—C22—C21−179.0 (3)
C4—C3—C8—C70.3 (4)C17—C18—C19—C200.0 (8)
C4—C3—C8—C7A0.3 (4)C18—C17—C22—C210.6 (5)
C4—C5—C6—C7−1.3 (4)C18—C19—C20—C21−0.3 (8)
C4—C5—C6A—C7A−1.3 (4)C19—C20—C21—C220.8 (6)
C4—C5—C6A—C23A176.4 (3)C20—C21—C22—C17−0.9 (5)
C5—C6—C7—C81.3 (4)C22—C17—C18—C19−0.1 (6)
C5—C6—C7—C23−175.1 (3)C23—C7—C8—C3175.4 (3)
C5—C6A—C7A—C81.3 (4)C23A—C6A—C7A—C8−176.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···N10.932.733.348 (5)125
 

Acknowledgements

JPJ acknowledges the NSF–MRI program (Grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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ISSN: 2414-3146
Volume 2| Part 9| September 2017| x171258
https://doi.org/10.1107/S2414314617012585
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