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

Journal logoIUCrDATA
ISSN: 2414-3146

N-Ethyl-N′-(3-methyl­benzo­yl)-S,S-di­phenyl­sulfo­di­imide

aDepartment of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, bCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, and cGraduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
*Correspondence e-mail: by4ut6@bma.biglobe.ne.jp

Edited by H. Ishida, Okayama University, Japan (Received 21 June 2019; accepted 2 July 2019; online 15 July 2019)

The asymmetric unit of the title sulfodi­imide, C22H22N2OS, consists of two crystallographically independent mol­ecules with similar conformations The environment around each sulfur atom is a slightly distorted tetra­hedron with two S=N bonds and two S—C bonds. The S= N(m-methyl­benzo­yl) and S=N(NEt) bond lengths are 1.584 (3) and 1.528 (2) Å, respectively, for one mol­ecule, and 1.575 (2) and 1.529 (3) Å, respectively, for the other. The dihedral angles between the two phenyl rings in the mol­ecules are 86.76 (8) and 82.49 (8)°. The N—S—N—C(m-methyl­benzo­yl) and N—S—N—C(eth­yl) torsion angles are −60.5 (2) and −50.28 (19)°, respectively, for one mol­ecule, and 62.9 (2) and 44.2 (3)°, respectively, for the other. In the crystal, each independent mol­ecule is linked to its inversion-related mol­ecule via a pair of C—H⋯O hydrogen bonds, forming a dimer.

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

Structure description

Sulfoximines and sulfonedi­imines are relatively unexplored organic compounds in the aza analogues of sulfones family. The latter display various biological activities (Sellinger et al., 1969[Sellinger, O. Z. & Ohlsson, W. G. (1969). J. Neurochem. 16, 1193-1195.]; Kennewell et al., 1975[Kennewell, P. D. & Taylor, J. B. (1975). Chem. Soc. Rev. 4, 189-209.]; Haake, 1976[Haake, M. (1976). Topics in Sulfur Chemistry, Vol. 1, edited by A. Senning. Stuttgart: George Thieme Verlag.]; Park et al., 2011[Park, S. J., Buschmann, H. & Bolm, C. (2011). Bioorg. Med. Chem. Lett. 21, 4888-4890.]; Sparks et al., 2013[Sparks, T. C., Watson, G. B., Loso, M. R., Geng, C., Babcock, J. M. & Thomas, J. D. (2013). Pestic. Biochem. Physiol. 107, 1-7.]; Chen et al., 2012[Chen, X. Y., Park, S. J., Buschmann, H., De Rosa, M. & Bolm, C. (2012). Bioorg. Med. Chem. Lett. 22, 4307-4309]). In view of the biological activities of these sulfones, which are related to structural aspects, and as part of our studies on N-tosyl-sulfonedi­imine (Sheikh et al., 2019[Sheikh, M. C., Yoshimura, T. & Miyatake, R. (2019). IUCrData, 4, x190523.]), we report herein the synthesis and crystal structure of the title compound (Fig. 1[link]). The S1—N1 (m-methyl­benzo­yl) and S1—N2 (NEt) bond lengths are 1.584 (3) and 1.528 (2) Å, respectively [1.575 (2) and 1.529 (3) Å in the other independent mol­ecule], which are significantly longer than the S≡N triple bond of tri­phenyl­sulfane­nitrile (1.462 Å; Yoshimura et al., 1997[Yoshimura, T., Hamada, K., Imado, M., Hamata, K., Tomoda, T., Fujii, T., Morita, H., Shimasaki, S., Ono, S., Tsukurimichi, E., Furukawa, N. & Kimura, T. (1997). J. Org. Chem. 62, 3802-3803.]), and close to the S=N double bonds of S,S-di­methyl­sulfonedi­imine (1.533 Å, electron diffraction; Oberhammer et al., 1970[Oberhammer, H. & Zeil, W. (1970). Z. Naturforsch. Teil A, 25, 845-849.]), S,S-diphenyl-S-pyrrolidino­imino­sulfonium perchlorate [1.503 (2) Å for S—N (NH), X-ray; Sheikh et al., 2017[Sheikh, M. C., Yoshimura, T., Takata, E., Fujii, T. & Miyatake, R. (2017). IUCrData, 2, x171251.]] and S,S-di­phenyl­sulfodi­imide-N-phenyl [1.526 Å for S—N (NH) and 1.546 (1) Å for S—N (Ph), X-ray; Yoshimura et al., 2008[Yoshimura, T., Ishikawa, H., Fujie, T., Takata, E., Miyatake, R., Kita, H. & Tsukurimichi, E. (2008). Synthesis, pp. 1835-1840.]], and shorter than the S—N bond of S,S-diphenyl-N-tosyl­sulfilimine (1.628 Å, X-ray; Kálmán et al., 1971[Kálmán, A., Duffin, B. & Kucsman, Á. (1971). Acta Cryst. B27, 586-594.]). The N—S—N bond angles are larger than 109.5° expected for the sp3 hybrid configuration, while the N—S—C and C—S—C bond angles are smaller.

[Figure 1]
Figure 1
A view of the two independent mol­ecules of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, the two independent mol­ecules are each linked via a pair of C—H⋯O hydrogen bonds, forming inversion dimers with an R22(16) ring motif (Fig. 2[link] and Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H14⋯O1i 0.95 2.37 3.307 (4) 170
C39—H36⋯O2ii 0.95 2.35 3.296 (4) 173
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -z+1.
[Figure 2]
Figure 2
A view of the title compound, showing a pair of C—H⋯O hydrogen bonds (blue dashed lines) forming an R22(16) ring motif (S1-containing molecule is shown).

Synthesis and crystallization

The compound precursor, N-ethyl-S,S-di­phenyl­sulfodi­imide (100 mg, 0.40 mmol) was allowed to react with m-methyl­benzoyl chloride (80.3 mg, 0.52 mmol) in dry pyridine (100 μmol) at room temperature for 25 min. The reaction mixture was washed, poured into water, acidified with 3% H2SO4, and extracted with CHCl3 (3 × 10 ml). The combined organic layer washed with 10% aq. NaOH and with water, and then dried over anhydrous MgSO4. The solution was concentrated under reduced pressure affording the title compound was collected as a colourless solid and crystallized from a hot ethanol solution (yield: 84.0 mg, 90%; m.p. 140–141°C).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C22H22N2OS
Mr 362.49
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 173
a, b, c (Å) 11.0780 (2), 13.2775 (3), 13.3258 (3)
α, β, γ (°) 91.717 (1), 100.9442 (10), 90.9017 (10)
V3) 1923.08 (6)
Z 4
Radiation type Cu Kα
μ (mm−1) 1.58
Crystal size (mm) 0.46 × 0.27 × 0.17
 
Data collection
Diffractometer Rigaku R-AXIS RAPID
Absorption correction Multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.436, 0.770
No. of measured, independent and observed [F2 > 2σ(F2)] reflections 22182, 6901, 4159
Rint 0.099
(sin θ/λ)max−1) 0.602
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.151, 0.94
No. of reflections 6901
No. of parameters 473
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.47, −0.38
Computer programs: RAPID-AUTO (Rigaku, 2001[Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]), SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Structural data


Computing details top

Cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

N-[(Ethylimino)diphenyl-λ6-sulfanylidene]-3-methylbenzamide top
Crystal data top
C22H22N2OSZ = 4
Mr = 362.49F(000) = 768.00
Triclinic, P1Dx = 1.252 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54187 Å
a = 11.0780 (2) ÅCell parameters from 17291 reflections
b = 13.2775 (3) Åθ = 3.3–68.4°
c = 13.3258 (3) ŵ = 1.58 mm1
α = 91.717 (1)°T = 173 K
β = 100.9442 (10)°Platelet, colorless
γ = 90.9017 (10)°0.46 × 0.27 × 0.17 mm
V = 1923.08 (6) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4159 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.099
ω scansθmax = 68.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1313
Tmin = 0.436, Tmax = 0.770k = 1515
22182 measured reflectionsl = 1616
6901 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0704P)2]
where P = (Fo2 + 2Fc2)/3
6901 reflections(Δ/σ)max < 0.001
473 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.38 e Å3
Primary atom site location: structure-invariant direct methods
Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.05317 (6)0.61479 (5)0.25436 (5)0.0437 (2)
S20.33971 (6)0.11964 (5)0.24369 (5)0.0437 (2)
O10.23346 (16)0.48853 (14)0.36079 (15)0.0633 (6)
O20.20456 (16)0.01130 (14)0.34751 (16)0.0650 (6)
N10.19221 (19)0.61318 (16)0.24099 (16)0.0475 (6)
N20.03602 (18)0.52441 (15)0.23212 (16)0.0493 (6)
N30.19529 (18)0.11556 (15)0.23012 (15)0.0434 (6)
N40.41579 (19)0.03189 (16)0.21521 (16)0.0509 (6)
C10.3969 (3)0.54786 (19)0.28407 (19)0.0428 (7)
C20.4785 (3)0.4807 (2)0.3372 (2)0.0473 (7)
C30.6002 (3)0.4774 (2)0.3254 (2)0.0494 (7)
C40.6399 (3)0.5449 (2)0.2601 (2)0.0511 (8)
C50.5604 (3)0.6128 (2)0.2073 (2)0.0505 (8)
C60.4386 (3)0.61333 (19)0.21783 (19)0.0447 (7)
C70.6861 (3)0.4019 (3)0.3822 (3)0.0671 (9)
C80.2661 (3)0.5456 (2)0.2999 (2)0.0481 (7)
C90.0020 (3)0.71746 (19)0.17606 (18)0.0422 (7)
C100.0785 (3)0.77799 (19)0.1321 (2)0.0516 (8)
C110.0294 (3)0.8534 (3)0.0691 (3)0.0599 (9)
C120.0948 (3)0.8698 (2)0.0508 (2)0.0580 (8)
C130.1718 (3)0.8105 (2)0.0952 (3)0.0575 (8)
C140.1240 (3)0.7346 (2)0.1581 (2)0.0519 (8)
C150.0389 (3)0.65915 (18)0.37817 (19)0.0414 (7)
C160.0374 (3)0.6097 (2)0.4320 (2)0.0491 (7)
C170.0476 (3)0.6478 (3)0.5276 (2)0.0583 (8)
C180.0186 (3)0.7323 (3)0.5676 (3)0.0623 (9)
C190.0957 (3)0.7809 (2)0.5137 (3)0.0603 (8)
C200.1065 (3)0.7447 (2)0.4187 (2)0.0516 (8)
C210.0438 (3)0.4717 (3)0.1319 (3)0.0648 (9)
C220.1434 (4)0.3937 (3)0.1150 (3)0.0992 (13)
C230.0078 (3)0.04398 (19)0.26800 (19)0.0415 (7)
C240.0516 (3)0.02016 (19)0.3237 (2)0.0476 (7)
C250.1792 (3)0.0255 (2)0.3110 (3)0.0520 (8)
C260.2467 (3)0.0374 (2)0.2409 (3)0.0551 (8)
C270.1889 (3)0.1027 (2)0.1847 (2)0.0554 (8)
C280.0613 (3)0.10573 (19)0.19778 (19)0.0466 (7)
C290.2404 (3)0.0967 (3)0.3727 (3)0.0743 (10)
C300.1458 (3)0.0460 (2)0.2862 (2)0.0464 (7)
C310.3579 (3)0.22967 (19)0.17269 (18)0.0424 (7)
C320.4696 (3)0.2423 (2)0.1429 (2)0.0575 (8)
C330.4901 (3)0.3245 (3)0.0867 (3)0.0638 (9)
C340.3985 (3)0.3937 (3)0.0621 (2)0.0575 (8)
C350.2879 (3)0.3818 (2)0.0925 (2)0.0543 (8)
C360.2668 (3)0.2995 (2)0.14851 (19)0.0495 (7)
C370.4115 (3)0.15642 (19)0.36964 (19)0.0418 (7)
C380.5126 (3)0.1052 (2)0.4187 (2)0.0504 (7)
C390.5688 (3)0.1355 (3)0.5173 (3)0.0567 (8)
C400.5238 (3)0.2155 (3)0.5649 (3)0.0590 (9)
C410.4221 (3)0.2665 (2)0.5160 (2)0.0577 (8)
C420.3656 (3)0.2374 (2)0.4175 (2)0.0501 (7)
C430.3710 (3)0.0217 (3)0.1178 (3)0.0690 (9)
C440.4426 (4)0.1135 (3)0.1098 (3)0.0883 (12)
H10.45030.43610.38260.0568*
H20.72310.54440.25170.0613*
H30.58950.65900.16380.0606*
H40.38330.65840.17980.0537*
H50.75040.38590.34330.0805*
H60.63960.34030.39050.0805*
H70.72390.43060.44970.0805*
H80.16470.76770.14520.0620*
H90.08200.89440.03790.0719*
H100.12770.92220.00740.0697*
H110.25770.82190.08250.0690*
H120.17690.69380.18910.0622*
H130.08210.55050.40390.0589*
H140.10060.61530.56550.0700*
H150.01140.75800.63340.0748*
H160.14140.83940.54260.0723*
H170.15930.77760.38100.0619*
H180.03560.43970.12900.0777*
H190.05980.52100.07690.0777*
H200.12920.34630.17090.1190*
H210.14400.35720.04990.1190*
H220.22270.42600.11320.1190*
H230.00390.06180.37210.0571*
H240.33390.03570.23120.0662*
H250.23650.14530.13730.0665*
H260.02160.14990.15880.0559*
H270.19340.15870.38250.0892*
H280.32420.11290.33630.0892*
H290.24330.06480.43950.0892*
H300.53230.19450.16090.0690*
H310.56650.33330.06520.0766*
H320.41230.45040.02360.0690*
H330.22560.43000.07500.0652*
H340.19050.29120.17020.0594*
H350.54310.04970.38520.0605*
H360.63820.10080.55160.0680*
H370.56280.23630.63230.0708*
H380.39130.32150.55010.0693*
H390.29640.27230.38320.0601*
H400.37840.02280.06090.0828*
H410.28310.04040.11230.0828*
H420.52930.09470.11350.1059*
H430.41090.14920.04440.1059*
H440.43510.15750.16610.1059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0368 (4)0.0468 (5)0.0487 (4)0.0005 (4)0.0104 (3)0.0066 (3)
S20.0351 (4)0.0450 (5)0.0502 (4)0.0014 (4)0.0059 (3)0.0022 (3)
O10.0473 (12)0.0719 (14)0.0776 (14)0.0055 (11)0.0248 (11)0.0311 (12)
O20.0406 (13)0.0670 (14)0.0849 (15)0.0002 (11)0.0018 (11)0.0298 (12)
N10.0337 (13)0.0506 (15)0.0601 (15)0.0050 (11)0.0124 (11)0.0101 (12)
N20.0435 (14)0.0503 (14)0.0543 (14)0.0071 (12)0.0104 (11)0.0021 (12)
N30.0329 (12)0.0484 (14)0.0472 (13)0.0028 (11)0.0029 (10)0.0073 (11)
N40.0430 (14)0.0478 (14)0.0606 (15)0.0072 (12)0.0080 (11)0.0079 (12)
C10.0372 (16)0.0416 (16)0.0501 (16)0.0009 (13)0.0100 (13)0.0017 (13)
C20.0413 (17)0.0468 (18)0.0541 (17)0.0002 (14)0.0088 (13)0.0064 (14)
C30.0395 (17)0.0508 (18)0.0555 (18)0.0010 (15)0.0032 (14)0.0020 (14)
C40.0345 (16)0.060 (2)0.0595 (19)0.0004 (15)0.0108 (14)0.0010 (15)
C50.0459 (18)0.0523 (19)0.0552 (18)0.0005 (15)0.0136 (14)0.0083 (15)
C60.0395 (16)0.0447 (17)0.0503 (17)0.0019 (14)0.0089 (13)0.0029 (13)
C70.0442 (19)0.075 (3)0.080 (3)0.0084 (17)0.0045 (16)0.0207 (18)
C80.0434 (17)0.0464 (18)0.0567 (18)0.0009 (15)0.0150 (14)0.0009 (14)
C90.0386 (16)0.0466 (17)0.0407 (15)0.0033 (14)0.0046 (12)0.0064 (12)
C100.0458 (17)0.0529 (19)0.0572 (18)0.0003 (15)0.0104 (14)0.0137 (15)
C110.059 (2)0.057 (2)0.061 (2)0.0041 (17)0.0020 (16)0.0190 (16)
C120.071 (3)0.0489 (19)0.0479 (17)0.0053 (17)0.0070 (16)0.0093 (14)
C130.0493 (19)0.055 (2)0.066 (2)0.0063 (16)0.0028 (15)0.0111 (16)
C140.0441 (18)0.0521 (18)0.0597 (18)0.0032 (15)0.0085 (14)0.0141 (15)
C150.0362 (15)0.0406 (16)0.0469 (16)0.0051 (13)0.0061 (12)0.0041 (12)
C160.0492 (18)0.0465 (17)0.0529 (17)0.0006 (14)0.0118 (14)0.0087 (14)
C170.063 (2)0.063 (2)0.0549 (19)0.0086 (17)0.0235 (16)0.0096 (16)
C180.079 (3)0.058 (2)0.0496 (18)0.0191 (19)0.0106 (17)0.0015 (16)
C190.071 (3)0.0470 (18)0.0581 (19)0.0004 (16)0.0003 (16)0.0026 (15)
C200.0476 (18)0.0503 (18)0.0556 (18)0.0015 (15)0.0063 (14)0.0066 (14)
C210.060 (2)0.073 (3)0.061 (2)0.0001 (18)0.0128 (16)0.0069 (17)
C220.100 (3)0.094 (3)0.106 (3)0.034 (3)0.035 (3)0.044 (3)
C230.0391 (16)0.0403 (16)0.0441 (15)0.0012 (13)0.0060 (12)0.0008 (12)
C240.0432 (17)0.0441 (17)0.0553 (17)0.0013 (14)0.0084 (14)0.0062 (14)
C250.0433 (18)0.0495 (18)0.0651 (19)0.0038 (15)0.0152 (15)0.0020 (15)
C260.0357 (17)0.060 (2)0.070 (2)0.0021 (15)0.0112 (15)0.0031 (16)
C270.0390 (17)0.063 (2)0.0614 (19)0.0046 (16)0.0019 (14)0.0091 (15)
C280.0402 (17)0.0474 (17)0.0516 (17)0.0003 (14)0.0072 (13)0.0041 (13)
C290.055 (2)0.076 (3)0.098 (3)0.0025 (18)0.0288 (18)0.020 (2)
C300.0430 (17)0.0460 (18)0.0481 (17)0.0022 (15)0.0037 (13)0.0019 (14)
C310.0392 (16)0.0481 (17)0.0384 (14)0.0050 (14)0.0036 (12)0.0024 (12)
C320.0473 (18)0.056 (2)0.072 (2)0.0020 (16)0.0183 (15)0.0036 (16)
C330.057 (2)0.064 (3)0.075 (3)0.0103 (18)0.0264 (17)0.0026 (17)
C340.070 (3)0.054 (2)0.0514 (18)0.0129 (18)0.0221 (16)0.0007 (15)
C350.058 (2)0.0527 (19)0.0525 (18)0.0007 (16)0.0100 (15)0.0089 (14)
C360.0432 (17)0.0552 (19)0.0505 (17)0.0015 (15)0.0093 (13)0.0071 (14)
C370.0342 (15)0.0418 (16)0.0496 (16)0.0034 (13)0.0083 (12)0.0053 (13)
C380.0414 (17)0.0487 (18)0.0579 (18)0.0032 (15)0.0018 (14)0.0014 (14)
C390.0503 (19)0.055 (2)0.0588 (19)0.0025 (16)0.0042 (15)0.0085 (16)
C400.070 (3)0.054 (2)0.0495 (18)0.0111 (18)0.0039 (16)0.0067 (16)
C410.075 (3)0.0490 (19)0.0515 (18)0.0055 (17)0.0188 (16)0.0025 (15)
C420.0478 (18)0.0502 (18)0.0538 (18)0.0025 (15)0.0128 (14)0.0039 (14)
C430.069 (3)0.067 (3)0.069 (3)0.0003 (19)0.0100 (17)0.0142 (17)
C440.101 (3)0.064 (3)0.094 (3)0.017 (3)0.006 (3)0.024 (2)
Geometric parameters (Å, º) top
S1—N11.584 (3)C37—C421.386 (4)
S1—N21.528 (2)C38—C391.387 (4)
S1—C91.776 (3)C39—C401.370 (5)
S1—C151.771 (3)C40—C411.388 (5)
S2—N31.575 (2)C41—C421.384 (4)
S2—N41.529 (3)C43—C441.476 (5)
S2—C311.793 (3)C2—H10.950
S2—C371.766 (3)C4—H20.950
O1—C81.226 (4)C5—H30.950
O2—C301.234 (4)C6—H40.950
N1—C81.383 (4)C7—H50.980
N2—C211.477 (4)C7—H60.980
N3—C301.376 (4)C7—H70.980
N4—C431.458 (4)C10—H80.950
C1—C21.391 (4)C11—H90.950
C1—C61.391 (4)C12—H100.950
C1—C81.504 (4)C13—H110.950
C2—C31.387 (4)C14—H120.950
C3—C41.391 (4)C16—H130.950
C3—C71.512 (4)C17—H140.950
C4—C51.382 (4)C18—H150.950
C5—C61.383 (4)C19—H160.950
C9—C101.379 (4)C20—H170.950
C9—C141.394 (4)C21—H180.990
C10—C111.378 (4)C21—H190.990
C11—C121.373 (5)C22—H200.980
C12—C131.377 (5)C22—H210.980
C13—C141.378 (4)C22—H220.980
C15—C161.379 (4)C24—H230.950
C15—C201.387 (4)C26—H240.950
C16—C171.381 (4)C27—H250.950
C17—C181.369 (4)C28—H260.950
C18—C191.380 (5)C29—H270.980
C19—C201.368 (5)C29—H280.980
C21—C221.482 (5)C29—H290.980
C23—C241.384 (4)C32—H300.950
C23—C281.388 (4)C33—H310.950
C23—C301.501 (4)C34—H320.950
C24—C251.391 (4)C35—H330.950
C25—C261.389 (4)C36—H340.950
C25—C291.506 (5)C38—H350.950
C26—C271.387 (5)C39—H360.950
C27—C281.391 (4)C40—H370.950
C31—C321.379 (5)C41—H380.950
C31—C361.380 (4)C42—H390.950
C32—C331.383 (5)C43—H400.990
C33—C341.380 (5)C43—H410.990
C34—C351.369 (5)C44—H420.980
C35—C361.383 (4)C44—H430.980
C37—C381.384 (4)C44—H440.980
N1—S1—N2124.42 (12)C5—C6—H4119.968
N1—S1—C999.34 (13)C3—C7—H5109.471
N1—S1—C15111.93 (12)C3—C7—H6109.464
N2—S1—C9111.85 (12)C3—C7—H7109.468
N2—S1—C15104.30 (13)H5—C7—H6109.476
C9—S1—C15103.29 (12)H5—C7—H7109.473
N3—S2—N4123.76 (12)H6—C7—H7109.476
N3—S2—C3199.52 (12)C9—C10—H8120.147
N3—S2—C37112.11 (12)C11—C10—H8120.146
N4—S2—C31112.28 (13)C10—C11—H9119.703
N4—S2—C37104.46 (12)C12—C11—H9119.707
C31—S2—C37103.05 (12)C11—C12—H10119.929
S1—N1—C8115.9 (2)C13—C12—H10119.927
S1—N2—C21116.3 (2)C12—C13—H11120.065
S2—N3—C30116.68 (17)C14—C13—H11120.058
S2—N4—C43117.30 (18)C9—C14—H12120.002
C2—C1—C6119.1 (3)C13—C14—H12120.010
C2—C1—C8118.2 (3)C15—C16—H13120.622
C6—C1—C8122.7 (3)C17—C16—H13120.632
C1—C2—C3121.5 (3)C16—C17—H14120.016
C2—C3—C4118.2 (3)C18—C17—H14120.021
C2—C3—C7120.4 (3)C17—C18—H15119.515
C4—C3—C7121.5 (3)C19—C18—H15119.521
C3—C4—C5121.2 (3)C18—C19—H16120.020
C4—C5—C6120.0 (3)C20—C19—H16120.030
C1—C6—C5120.1 (3)C15—C20—H17120.536
O1—C8—N1125.9 (3)C19—C20—H17120.541
O1—C8—C1120.8 (3)N2—C21—H18109.481
N1—C8—C1113.3 (3)N2—C21—H19109.485
S1—C9—C10124.0 (2)C22—C21—H18109.482
S1—C9—C14116.3 (2)C22—C21—H19109.486
C10—C9—C14119.7 (3)H18—C21—H19108.061
C9—C10—C11119.7 (3)C21—C22—H20109.477
C10—C11—C12120.6 (3)C21—C22—H21109.473
C11—C12—C13120.1 (3)C21—C22—H22109.473
C12—C13—C14119.9 (3)H20—C22—H21109.466
C9—C14—C13120.0 (3)H20—C22—H22109.468
S1—C15—C16120.58 (19)H21—C22—H22109.471
S1—C15—C20118.0 (2)C23—C24—H23119.002
C16—C15—C20121.4 (3)C25—C24—H23119.002
C15—C16—C17118.7 (3)C25—C26—H24119.443
C16—C17—C18120.0 (3)C27—C26—H24119.445
C17—C18—C19121.0 (3)C26—C27—H25119.967
C18—C19—C20120.0 (3)C28—C27—H25119.963
C15—C20—C19118.9 (3)C23—C28—H26120.158
N2—C21—C22110.8 (3)C27—C28—H26120.160
C24—C23—C28119.3 (3)C25—C29—H27109.470
C24—C23—C30119.0 (3)C25—C29—H28109.465
C28—C23—C30121.6 (3)C25—C29—H29109.464
C23—C24—C25122.0 (3)H27—C29—H28109.481
C24—C25—C26117.8 (3)H27—C29—H29109.477
C24—C25—C29120.3 (3)H28—C29—H29109.472
C26—C25—C29121.8 (3)C31—C32—H30120.054
C25—C26—C27121.1 (3)C33—C32—H30120.045
C26—C27—C28120.1 (3)C32—C33—H31120.370
C23—C28—C27119.7 (3)C34—C33—H31120.363
O2—C30—N3125.7 (3)C33—C34—H32119.564
O2—C30—C23120.1 (3)C35—C34—H32119.555
N3—C30—C23114.2 (3)C34—C35—H33119.978
S2—C31—C32116.4 (2)C36—C35—H33119.972
S2—C31—C36123.0 (3)C31—C36—H34120.341
C32—C31—C36120.6 (3)C35—C36—H34120.338
C31—C32—C33119.9 (3)C37—C38—H35120.260
C32—C33—C34119.3 (3)C39—C38—H35120.266
C33—C34—C35120.9 (3)C38—C39—H36120.115
C34—C35—C36120.0 (3)C40—C39—H36120.121
C31—C36—C35119.3 (3)C39—C40—H37119.601
S2—C37—C38120.1 (2)C41—C40—H37119.611
S2—C37—C42118.89 (19)C40—C41—H38120.000
C38—C37—C42121.0 (3)C42—C41—H38120.006
C37—C38—C39119.5 (3)C37—C42—H39120.527
C38—C39—C40119.8 (3)C41—C42—H39120.529
C39—C40—C41120.8 (3)N4—C43—H40109.587
C40—C41—C42120.0 (3)N4—C43—H41109.584
C37—C42—C41118.9 (3)C44—C43—H40109.585
N4—C43—C44110.3 (3)C44—C43—H41109.593
C1—C2—H1119.237H40—C43—H41108.124
C3—C2—H1119.239C43—C44—H42109.477
C3—C4—H2119.421C43—C44—H43109.462
C5—C4—H2119.429C43—C44—H44109.467
C4—C5—H3120.008H42—C44—H43109.471
C6—C5—H3120.017H42—C44—H44109.475
C1—C6—H4119.971H43—C44—H44109.475
N1—S1—N2—C2150.28 (19)C1—C2—C3—C7178.5 (2)
N2—S1—N1—C860.5 (2)C2—C3—C4—C50.7 (4)
N1—S1—C9—C106.6 (2)C7—C3—C4—C5179.1 (3)
N1—S1—C9—C14172.15 (16)C3—C4—C5—C60.9 (4)
C9—S1—N1—C8174.73 (15)C4—C5—C6—C12.1 (4)
N1—S1—C15—C16134.65 (17)S1—C9—C10—C11177.38 (16)
N1—S1—C15—C2045.4 (2)S1—C9—C14—C13177.73 (16)
C15—S1—N1—C866.22 (18)C10—C9—C14—C131.1 (4)
N2—S1—C9—C10139.73 (18)C14—C9—C10—C111.4 (4)
N2—S1—C9—C1439.1 (2)C9—C10—C11—C121.0 (4)
C9—S1—N2—C2168.84 (17)C10—C11—C12—C130.3 (4)
N2—S1—C15—C162.3 (2)C11—C12—C13—C140.0 (4)
N2—S1—C15—C20177.61 (16)C12—C13—C14—C90.4 (4)
C15—S1—N2—C21179.80 (13)S1—C15—C16—C17178.83 (15)
C9—S1—C15—C16119.40 (18)S1—C15—C20—C19179.27 (16)
C9—S1—C15—C2060.56 (19)C16—C15—C20—C190.7 (4)
C15—S1—C9—C10108.68 (19)C20—C15—C16—C171.1 (4)
C15—S1—C9—C1472.53 (18)C15—C16—C17—C180.9 (4)
N3—S2—N4—C4344.2 (3)C16—C17—C18—C190.2 (5)
N4—S2—N3—C3062.9 (2)C17—C18—C19—C200.2 (5)
N3—S2—C31—C32162.49 (16)C18—C19—C20—C150.0 (4)
N3—S2—C31—C3617.8 (2)C24—C23—C28—C270.3 (4)
C31—S2—N3—C30172.07 (14)C28—C23—C24—C250.6 (4)
N3—S2—C37—C38135.29 (18)C24—C23—C30—O22.5 (4)
N3—S2—C37—C4245.2 (3)C24—C23—C30—N3177.3 (2)
C37—S2—N3—C3063.70 (18)C30—C23—C24—C25179.7 (2)
N4—S2—C31—C3229.83 (19)C28—C23—C30—O2178.4 (3)
N4—S2—C31—C36150.48 (16)C28—C23—C30—N31.8 (4)
C31—S2—N4—C4375.06 (18)C30—C23—C28—C27178.8 (2)
N4—S2—C37—C381.1 (3)C23—C24—C25—C261.0 (4)
N4—S2—C37—C42178.40 (18)C23—C24—C25—C29179.7 (3)
C37—S2—N4—C43173.98 (16)C24—C25—C26—C270.6 (4)
C31—S2—C37—C38118.6 (2)C29—C25—C26—C27179.9 (3)
C31—S2—C37—C4260.9 (2)C25—C26—C27—C280.2 (4)
C37—S2—C31—C3282.01 (18)C26—C27—C28—C230.7 (4)
C37—S2—C31—C3697.68 (19)S2—C31—C32—C33179.12 (16)
S1—N1—C8—O10.5 (4)S2—C31—C36—C35179.28 (15)
S1—N1—C8—C1179.82 (14)C32—C31—C36—C351.0 (4)
S1—N2—C21—C22173.34 (15)C36—C31—C32—C331.2 (4)
S2—N3—C30—O21.8 (4)C31—C32—C33—C340.7 (4)
S2—N3—C30—C23178.52 (14)C32—C33—C34—C350.1 (4)
S2—N4—C43—C44170.70 (17)C33—C34—C35—C360.0 (4)
C2—C1—C6—C51.5 (4)C34—C35—C36—C310.4 (4)
C6—C1—C2—C30.2 (4)S2—C37—C38—C39179.39 (17)
C2—C1—C8—O12.5 (4)S2—C37—C42—C41179.71 (17)
C2—C1—C8—N1178.1 (2)C38—C37—C42—C410.2 (4)
C8—C1—C2—C3179.1 (2)C42—C37—C38—C390.1 (4)
C6—C1—C8—O1178.2 (3)C37—C38—C39—C400.0 (5)
C6—C1—C8—N11.2 (4)C38—C39—C40—C410.3 (5)
C8—C1—C6—C5179.2 (2)C39—C40—C41—C420.7 (5)
C1—C2—C3—C41.3 (4)C40—C41—C42—C370.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H14···O1i0.952.373.307 (4)170
C39—H36···O2ii0.952.353.296 (4)173
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y, z+1.
 

Acknowledgements

The authors are grateful to the Department of Applied Chemistry, Faculty of Engineering, University of Toyama for the provision of laboratory facilities and the Center for Environmental Conservation and Research Safety, University of Toyama, Japan, for providing facilities for single-crystal X-ray analyses.

Funding information

This work was supported in part by the Japan Society for the Promotion of Science, JSPS (No. P11336).

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