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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 4| Part 4| April 2019| x190523
https://doi.org/10.1107/S2414314619005236

S,S-Di­phenyl-N-tosyl sulfone di­imine

CROSSMARK_Color_square_no_text.svg
Md. Chanmiya Sheikh,a Toshiaki Yoshimuraa* and Ryuta Miyatakeb

aDepartment of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan, and bCenter for Environmental Conservation and Research Safety, 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 4 April 2019; accepted 16 April 2019; online 25 April 2019)

In the title compound [systematic name: N-(imino­diphenyl-λ6-sulfanyl­idene)-4-methyl­benzene-1-sulfonamide], C19H18N2O2S2, the configuration around the sulfur atom of the sulfonedi­imine group is a slightly distorted tetra­hedron structure with two S=N bonds and two S—C bonds. The bond lengths of S=N (p-toluene­sulfon­yl) and S=N (NH) are 1.5785 (15) and 1.5158 (18) Å, respectively. The S—N=S plane makes a dihedral angle of 74.24 (14)° with the p-toluene ring, while it makes dihedral angles of 73.43 (13) and 41.98 (14)° with the phenyl rings. The two torsion angles of S—N=S—C (phen­yl) and the S—N=S=N angle are 105.86 (12), −144.54 (11) and −25.67 (17)°, respectively. In the crystal, mol­ecules are connected by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R22(12) ring motif. The dimers are linked by C—H⋯O inter­actions, forming a tape structure along the a-axis direction.

CCDC reference: 1452477

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

Structure description

The aza analogues of sulfones such as sulfoximines and sulfonedi­imines have inter­esting pharmaceutical properties (Kennewell & Tavlor, 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.]; Sellinger et al., 1969[Sellinger, O. Z. & Ohlsson, W. G. (1969). J. Neurochem. 16, 1193-1195.]). However, their chemical reactivities have not been fully explored as yet except for a few scattered utilizations in organic syntheses for example as an alkyl­idene-transfer reagent (Johnson et al., 1973[Johnson, C. R., Kirchhoff, R. A., Reischer, R. J. & Katekar, G. F. J. (1973). J. Am. Chem. Soc. 95, 4287-4291.]). To date, some related crystal structures have been reported (Yoshimura et al., 2008[Yoshimura, T., Ishikawa, H., Fujie, T., Takata, E., Miyatake, R., Kita, H. & Tsukurimichi, E. (2008). Synthesis, pp. 1835-1840.]). As part of our studies in this area, we report herein on the synthesis and crystal structure of the title compound.

The mol­ecular structure of the title compound is illustrated in Fig. 1[link]. The S2—N1 and S2—N2 bond lengths are 1.5785 (15) and 1.5158 (18) Å, respectively. These bond lengths 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.]), close to the S=N double bond lengths of S,S-di­methyl­sulfonedi­imine (1.533 Å, electron diffraction study; Oberhammer & Zeil, 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 that 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 N1—S2—N2 bond angle [126.05 (9)°] is larger than 109.5°, while the N—S—C and C—S—C bond angles [102.92 (9)–112.96 (19)°] are close to 109.5°. In the crystal, the mol­ecules are linked through N—H⋯O and C—H⋯O hydrogen bonds (Table 1[link], Fig. 2[link]), forming a tape along the a-axis direction (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H8⋯O2i 0.89 (3) 2.20 (3) 3.018 (3) 152 (2)
C12—H12⋯O1ii 0.95 2.34 3.283 (2) 169
Symmetry codes: (i) -x, -y, -z+2; (ii) x-1, y, z.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2]
Figure 2
A view of the title compound showing a pair of N—H⋯O hydrogen bonds (blue dashed lines) forming an [R_{2}^{2}](12) ring motif.
[Figure 3]
Figure 3
A partial packing diagram of the title compound, showing the tape along the a-axis direction formed via N—H⋯O and C—H⋯O hydrogen bonds (blue dashed lines).

Synthesis and crystallization

The title compound was prepared by the method previously reported (Furukawa et al., 1984[Furukawa, N., Akutagawa, K. & Oae, S. (1984). Phosphorus Sulfur Relat. Elem. 20, 1-14.]) using S,S-di­phenyl­sulfilimide mono hydrate with chloramine-T in the presence of excess sodium salt of tosyl­amide in anhydrous aceto­nitrile and was crystallized from an ethanol solution (yield 90%; m.p. 153–154°C).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C19H18N2O2S2
Mr 370.48
Crystal system, space group Monoclinic, P21/c
Temperature (K) 173
a, b, c (Å) 9.47865 (17), 10.38462 (19), 18.0852 (4)
β (°) 97.4526 (7)
V (Å3) 1765.13 (6)
Z 4
Radiation type Cu Kα
μ (mm−1) 2.86
Crystal size (mm) 0.56 × 0.52 × 0.14
 
Data collection
Diffractometer Rigaku R-AXIS RAPID
Absorption correction Multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.500, 0.670
No. of measured, independent and observed [F2 > 2.0σ(F2)] reflections 19250, 3226, 2893
Rint 0.086
(sin θ/λ)max (Å−1) 0.602
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.127, 1.09
No. of reflections 3226
No. of parameters 231
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.83, −0.52
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

CCDC reference: 1452477

Crystal structure: contains datablocks General, I. DOI: https://doi.org/10.1107/S2414314619005236/is4032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619005236/is4032Isup2.hkl

List of Change. DOI: https://doi.org/10.1107/S2414314619005236/is4032sup3.pdf

Supporting information file. DOI: https://doi.org/10.1107/S2414314619005236/is4032Isup4.cml

checkCIF report


Computing details top

Cell refinement: 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-(Iminodiphenyl-λ6-sulfanylidene)-4-methylbenzene-1-sulfonamide top
Crystal data top
C19H18N2O2S2F(000) = 776.00
Mr = 370.48Dx = 1.394 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybcCell parameters from 18540 reflections
a = 9.47865 (17) Åθ = 4.3–68.2°
b = 10.38462 (19) ŵ = 2.86 mm−1
c = 18.0852 (4) ÅT = 173 K
β = 97.4526 (7)°Platelet, colorless
V = 1765.13 (6) Å30.56 × 0.52 × 0.14 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2893 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.086
ω scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −11→11
Tmin = 0.500, Tmax = 0.670k = −12→12
19250 measured reflectionsl = −21→21
3226 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0797P)2 + 0.2545P]
where P = (Fo2 + 2Fc2)/3
3226 reflections(Δ/σ)max = 0.001
231 parametersΔρmax = 0.83 e Å−3
0 restraintsΔρmin = −0.52 e Å−3
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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
S10.17740 (4)0.17061 (4)0.93189 (2)0.02550 (17)
S2−0.08500 (4)0.16500 (4)0.84447 (2)0.02510 (17)
O10.27017 (14)0.27580 (12)0.95689 (7)0.0345 (4)
O20.10643 (14)0.10862 (14)0.98795 (7)0.0375 (4)
N10.07009 (15)0.22168 (15)0.86291 (8)0.0299 (4)
N2−0.13277 (18)0.03177 (16)0.86480 (10)0.0349 (4)
C10.28321 (18)0.05373 (16)0.89394 (10)0.0251 (4)
C20.3026 (2)0.05765 (18)0.81932 (10)0.0332 (5)
C30.3949 (3)−0.02824 (19)0.79274 (11)0.0375 (5)
C40.4692 (2)−0.11932 (18)0.83931 (11)0.0357 (5)
C50.4450 (3)−0.1227 (2)0.91330 (12)0.0416 (5)
C60.3530 (3)−0.03744 (19)0.94066 (11)0.0362 (5)
C70.5717 (3)−0.2107 (3)0.81015 (14)0.0517 (6)
C8−0.19435 (18)0.29055 (17)0.87394 (9)0.0253 (4)
C9−0.1404 (2)0.41329 (18)0.88810 (10)0.0311 (4)
C10−0.2267 (3)0.50666 (19)0.91370 (11)0.0371 (5)
C11−0.3646 (3)0.4763 (2)0.92469 (11)0.0391 (5)
C12−0.4183 (2)0.3542 (2)0.90947 (11)0.0387 (5)
C13−0.33348 (19)0.25966 (19)0.88366 (10)0.0315 (5)
C14−0.1138 (2)0.16802 (16)0.74561 (10)0.0261 (4)
C15−0.1989 (2)0.07367 (18)0.70885 (11)0.0344 (5)
C16−0.2169 (3)0.0731 (2)0.63126 (12)0.0417 (5)
C17−0.1524 (3)0.1666 (2)0.59297 (12)0.0408 (5)
C18−0.0697 (3)0.2607 (2)0.63049 (11)0.0387 (5)
C19−0.0498 (2)0.26312 (18)0.70765 (10)0.0335 (5)
H10.25270.11890.78680.0398*
H20.4083−0.02530.74160.0450*
H30.4929−0.18510.94580.0500*
H40.3377−0.04150.99150.0435*
H50.5742−0.19430.75700.0620*
H60.5408−0.29950.81700.0620*
H70.6669−0.19810.83750.0620*
H8−0.124 (3)0.019 (3)0.9139 (14)0.046 (7)*
H9−0.04560.43320.88040.0373*
H10−0.19130.59130.92370.0445*
H11−0.42300.54020.94290.0469*
H12−0.51350.33490.91670.0464*
H13−0.36980.17550.87290.0378*
H14−0.24400.01080.73590.0413*
H15−0.27340.00840.60470.0501*
H16−0.16540.16600.54000.0489*
H17−0.02600.32430.60330.0464*
H180.00630.32830.73400.0402*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0227 (3)0.0297 (3)0.0239 (3)0.00039 (16)0.0021 (2)0.00052 (15)
S20.0231 (3)0.0256 (3)0.0264 (3)0.00086 (15)0.0024 (2)0.00271 (15)
O10.0313 (7)0.0336 (8)0.0374 (8)−0.0019 (6)−0.0003 (6)−0.0083 (6)
O20.0347 (8)0.0512 (9)0.0277 (7)0.0014 (7)0.0079 (6)0.0089 (6)
N10.0219 (8)0.0340 (9)0.0328 (9)0.0008 (7)0.0002 (7)0.0077 (7)
N20.0360 (9)0.0301 (9)0.0380 (10)−0.0026 (7)0.0028 (8)0.0061 (7)
C10.0233 (9)0.0246 (9)0.0267 (9)−0.0021 (7)0.0004 (7)−0.0006 (7)
C20.0386 (11)0.0321 (10)0.0287 (10)0.0064 (9)0.0041 (9)0.0061 (8)
C30.0440 (12)0.0363 (11)0.0334 (11)0.0061 (9)0.0094 (10)−0.0005 (8)
C40.0336 (11)0.0270 (10)0.0458 (12)0.0029 (8)0.0023 (9)−0.0043 (9)
C50.0459 (12)0.0348 (11)0.0415 (11)0.0123 (10)−0.0049 (10)0.0055 (9)
C60.0416 (12)0.0371 (11)0.0285 (10)0.0066 (9)−0.0010 (9)0.0046 (8)
C70.0517 (14)0.0382 (13)0.0662 (16)0.0148 (11)0.0114 (13)−0.0060 (11)
C80.0233 (9)0.0305 (10)0.0215 (9)0.0032 (8)0.0008 (7)0.0013 (7)
C90.0281 (9)0.0350 (11)0.0304 (10)−0.0016 (8)0.0043 (8)−0.0022 (8)
C100.0439 (12)0.0323 (11)0.0348 (10)0.0032 (9)0.0040 (9)−0.0021 (9)
C110.0411 (12)0.0445 (13)0.0323 (10)0.0139 (10)0.0078 (9)0.0009 (9)
C120.0268 (10)0.0532 (13)0.0372 (11)0.0054 (9)0.0089 (9)0.0065 (10)
C130.0265 (9)0.0355 (11)0.0320 (10)−0.0013 (8)0.0017 (8)0.0032 (8)
C140.0265 (9)0.0262 (10)0.0254 (9)0.0036 (7)0.0024 (8)0.0007 (7)
C150.0354 (11)0.0298 (10)0.0375 (11)−0.0027 (8)0.0029 (9)0.0010 (8)
C160.0449 (12)0.0389 (12)0.0386 (11)−0.0024 (10)−0.0052 (10)−0.0086 (9)
C170.0487 (13)0.0457 (13)0.0266 (10)0.0035 (10)−0.0004 (10)−0.0022 (9)
C180.0468 (12)0.0403 (12)0.0292 (10)−0.0018 (9)0.0052 (9)0.0049 (8)
C190.0391 (11)0.0305 (10)0.0306 (10)−0.0045 (8)0.0031 (9)−0.0007 (8)
Geometric parameters (Å, º) top
S1—O11.4380 (13)C15—C161.391 (3)
S1—O21.4394 (15)C16—C171.381 (4)
S1—N11.5947 (15)C17—C181.375 (3)
S1—C11.7688 (18)C18—C191.384 (3)
S2—N11.5785 (15)N2—H80.89 (3)
S2—N21.5158 (18)C2—H10.950
S2—C81.7893 (19)C3—H20.950
S2—C141.7735 (19)C5—H30.950
C1—C21.386 (3)C6—H40.950
C1—C61.379 (3)C7—H50.980
C2—C31.379 (3)C7—H60.980
C3—C41.395 (3)C7—H70.980
C4—C51.387 (3)C9—H90.950
C4—C71.502 (4)C10—H100.950
C5—C61.379 (3)C11—H110.950
C8—C91.385 (3)C12—H120.950
C8—C131.390 (3)C13—H130.950
C9—C101.386 (3)C15—H140.950
C10—C111.384 (3)C16—H150.950
C11—C121.380 (3)C17—H160.950
C12—C131.388 (3)C18—H170.950
C14—C151.384 (3)C19—H180.950
C14—C191.386 (3)
S1···N23.3570 (17)C12···H2iii3.0176
S2···O23.0244 (13)C12···H3iv3.3035
O1···C23.408 (3)C12···H5iii3.2164
O1···C63.368 (3)C12···H11xiv3.4108
O2···N23.070 (2)C12···H15xv3.3133
O2···C63.002 (3)C12···H16v3.1456
N1···C22.972 (3)C13···H2iii3.1945
N1···C92.896 (3)C13···H4iv3.2026
N1···C192.921 (3)C13···H5iii3.2245
N2···C133.083 (3)C13···H16v3.1559
N2···C152.842 (3)C15···H6iii3.4729
C1···C42.786 (3)C15···H9vi3.3276
C2···C52.761 (3)C15···H18vi3.2253
C3···C62.757 (3)C16···H6iii3.5778
C8···C112.748 (3)C16···H9vi2.9117
C8···C193.475 (3)C16···H11xvi3.5185
C9···C122.780 (3)C16···H12xvi3.5816
C10···C132.785 (3)C17···H3iii3.5623
C13···C143.581 (3)C17···H9vi3.0652
C14···C172.737 (3)C17···H10vi3.4010
C15···C182.781 (3)C18···H8iii3.40 (3)
C16···C192.783 (3)C18···H9vi3.5850
O1···C10i3.317 (3)C18···H10vi3.2861
O1···C11i3.394 (3)H1···C7x3.1191
O1···C12ii3.283 (3)H1···H5x2.7234
O1···C16iii3.481 (3)H1···H6x3.0033
O2···O2iv3.095 (2)H1···H7x3.1121
O2···N2iv3.018 (3)H2···C7x3.4100
O2···C18v3.520 (3)H2···C8vi3.3221
N2···O2iv3.018 (3)H2···C9vi3.2879
N2···C18vi3.402 (3)H2···C10vi3.1156
C5···C6vii3.478 (3)H2···C11vi2.9821
C5···C17vi3.523 (4)H2···C12vi3.0176
C6···C5vii3.478 (3)H2···C13vi3.1945
C6···C6vii3.380 (3)H2···H5x3.4413
C6···C18vi3.517 (3)H2···H6x2.6426
C10···O1i3.317 (3)H2···H11vi3.4262
C11···O1i3.394 (3)H2···H12vi3.4696
C12···O1viii3.283 (3)H2···H14ii3.3315
C16···O1vi3.481 (3)H3···S1vii3.5901
C17···C5iii3.523 (4)H3···O1vii2.8289
C18···O2ix3.520 (3)H3···C6vii3.3034
C18···N2iii3.402 (3)H3···C12iv3.3035
C18···C6iii3.517 (3)H3···C17vi3.5623
S1···H12.8584H3···H4vii2.9880
S1···H42.8101H3···H11xii2.9642
S1···H83.24 (3)H3···H12iv2.9179
S1···H93.5019H3···H16vi3.5068
S2···H13.5259H4···N2iv3.4420
S2···H92.8735H4···C5vii3.0320
S2···H132.8142H4···C6vii3.1367
S2···H142.8145H4···C13iv3.2026
S2···H182.8406H4···H3vii2.9880
O1···H13.4659H4···H4vii3.1712
O1···H43.3990H4···H8iv2.8271
O1···H93.5316H4···H13iv2.8027
O2···H42.6838H4···H16vi3.4609
O2···H82.58 (3)H4···H17vi3.5072
N1···H12.5786H5···C2xi3.2128
N1···H83.02 (3)H5···C12vi3.2164
N1···H92.4937H5···C13vi3.2245
N1···H182.5815H5···H1xi2.7234
N2···H132.7166H5···H2xi3.4413
N2···H142.4402H5···H12vi3.1335
C1···H23.2430H5···H13vi3.1487
C1···H33.2400H5···H14ii2.7970
C2···H43.2554H6···C2xi3.3804
C3···H33.2424H6···C3xi3.2034
C3···H52.5618H6···C10xii3.3114
C3···H63.1440H6···C11xii3.0923
C3···H73.1412H6···C15vi3.4729
C4···H13.2751H6···C16vi3.5778
C4···H43.2666H6···H1xi3.0033
C5···H23.2414H6···H2xi2.6426
C5···H53.3078H6···H10xii3.1916
C5···H62.7645H6···H11xii2.8057
C5···H72.7686H6···H14vi3.4652
C6···H13.2555H7···N2ii3.0502
C7···H22.6731H7···C10xii3.4584
C7···H32.6691H7···H1xi3.1121
C8···H82.97 (3)H7···H8ii3.1947
C8···H103.2493H7···H10xii2.9120
C8···H123.2507H7···H11xii3.4890
C8···H183.3808H7···H14ii3.0321
C9···H113.2533H7···H17xi3.4409
C9···H133.2776H7···H18xi3.5180
C9···H183.3896H8···S1iv3.50 (3)
C10···H123.2577H8···O2iv2.20 (3)
C11···H93.2581H8···C18vi3.40 (3)
C11···H133.2598H8···H4iv2.8271
C12···H103.2581H8···H7viii3.1947
C13···H83.20 (3)H8···H17vi2.5120
C13···H93.2772H9···C15iii3.3276
C13···H113.2546H9···C16iii2.9117
C14···H13.4944H9···C17iii3.0652
C14···H83.43 (3)H9···C18iii3.5850
C14···H133.5550H9···H15iii3.1003
C14···H153.2456H9···H16iii3.3423
C14···H173.2413H9···H16v3.3965
C15···H163.2554H10···S1i3.5867
C15···H183.2797H10···O1i2.7476
C16···H173.2519H10···O2i3.5465
C17···H143.2617H10···C7xiii3.5062
C17···H183.2544H10···C17iii3.4010
C18···H153.2523H10···C18iii3.2861
C19···H13.3835H10···H6xiii3.1916
C19···H93.5843H10···H7xiii2.9120
C19···H143.2802H10···H16iii3.4474
C19···H163.2478H10···H16v3.3903
H1···H22.3234H10···H17iii3.2546
H1···H183.2430H11···O1i2.8900
H2···H52.3486H11···C7xiii3.5250
H2···H63.3322H11···C11xiv3.3262
H2···H73.3361H11···C12xiv3.4108
H3···H42.3207H11···C16xv3.5185
H3···H53.5985H11···H2iii3.4262
H3···H62.7061H11···H3xiii2.9642
H3···H72.7235H11···H6xiii2.8057
H8···H132.8597H11···H7xiii3.4890
H8···H143.2723H11···H11xiv2.8055
H9···H102.3440H11···H12xiv2.9812
H9···H182.9627H11···H15xv2.9136
H10···H112.3297H11···H15v3.1221
H11···H122.3240H11···H16v3.5384
H12···H132.3460H12···S1viii3.4321
H13···H143.3530H12···O1viii2.3445
H14···H152.3540H12···C1viii3.4930
H15···H162.3251H12···C16xv3.5816
H16···H172.3167H12···H2iii3.4696
H17···H182.3434H12···H3iv2.9179
S1···H3vii3.5901H12···H5iii3.1335
S1···H8iv3.50 (3)H12···H11xiv2.9812
S1···H10i3.5867H12···H15xv2.6972
S1···H12ii3.4321H13···C1viii3.5904
O1···H3vii2.8289H13···C2viii3.3617
O1···H10i2.7476H13···C3viii3.2731
O1···H11i2.8900H13···C4viii3.4401
O1···H12ii2.3445H13···H4iv2.8027
O1···H15iii2.6614H13···H5iii3.1487
O2···H8iv2.20 (3)H14···C7viii3.2799
O2···H10i3.5465H14···H2viii3.3315
O2···H17vi3.4199H14···H5viii2.7970
O2···H17v2.6629H14···H6iii3.4652
N1···H15iii3.5536H14···H7viii3.0321
N2···H4iv3.4420H14···H18vi2.9405
N2···H7viii3.0502H15···O1vi2.6614
N2···H17vi2.6480H15···N1vi3.5536
N2···H18vi3.1056H15···C10ix3.5418
C1···H12ii3.4930H15···C11xvi3.4196
C1···H13ii3.5904H15···C11ix3.2616
C1···H17vi3.4140H15···C12xvi3.3133
C2···H5x3.2128H15···H9vi3.1003
C2···H6x3.3804H15···H11xvi2.9136
C2···H13ii3.3617H15···H11ix3.1221
C3···H6x3.2034H15···H12xvi2.6972
C3···H13ii3.2731H16···C6iii3.5956
C4···H13ii3.4401H16···C8ix3.0140
C5···H4vii3.0320H16···C9ix2.9069
C6···H3vii3.3034H16···C10ix2.9029
C6···H4vii3.1367H16···C11ix3.0131
C6···H16vi3.5956H16···C12ix3.1456
C6···H17vi3.4151H16···C13ix3.1560
C7···H1xi3.1191H16···H3iii3.5068
C7···H2xi3.4100H16···H4iii3.4609
C7···H10xii3.5062H16···H9vi3.3423
C7···H11xii3.5250H16···H9ix3.3965
C7···H14ii3.2799H16···H10vi3.4474
C8···H2iii3.3221H16···H10ix3.3903
C8···H16v3.0140H16···H11ix3.5384
C9···H2iii3.2879H17···O2iii3.4199
C9···H16v2.9069H17···O2ix2.6629
C10···H2iii3.1156H17···N2iii2.6480
C10···H6xiii3.3114H17···C1iii3.4140
C10···H7xiii3.4584H17···C6iii3.4151
C10···H15v3.5418H17···H4iii3.5072
C10···H16v2.9029H17···H7x3.4409
C11···H2iii2.9821H17···H8iii2.5120
C11···H6xiii3.0923H17···H10vi3.2546
C11···H11xiv3.3262H18···N2iii3.1056
C11···H15xv3.4196H18···C15iii3.2253
C11···H15v3.2616H18···H7x3.5180
C11···H16v3.0131H18···H14iii2.9405
O1—S1—O2116.16 (8)C17—C18—C19120.3 (2)
O1—S1—N1107.18 (8)C14—C19—C18118.38 (18)
O1—S1—C1106.79 (8)S2—N2—H8112.7 (15)
O2—S1—N1113.01 (8)C1—C2—H1120.300
O2—S1—C1107.86 (9)C3—C2—H1120.313
N1—S1—C1105.12 (8)C2—C3—H2119.289
N1—S2—N2126.05 (9)C4—C3—H2119.290
N1—S2—C8103.00 (8)C4—C5—H3119.292
N1—S2—C14102.92 (9)C6—C5—H3119.301
N2—S2—C8112.96 (10)C1—C6—H4120.122
N2—S2—C14104.42 (9)C5—C6—H4120.124
C8—S2—C14105.56 (8)C4—C7—H5109.473
S1—N1—S2121.56 (10)C4—C7—H6109.475
S1—C1—C2120.74 (14)C4—C7—H7109.479
S1—C1—C6118.96 (15)H5—C7—H6109.468
C2—C1—C6120.20 (18)H5—C7—H7109.464
C1—C2—C3119.39 (17)H6—C7—H7109.469
C2—C3—C4121.42 (19)C8—C9—H9120.460
C3—C4—C5117.80 (19)C10—C9—H9120.466
C3—C4—C7121.01 (19)C9—C10—H10120.070
C5—C4—C7121.19 (19)C11—C10—H10120.067
C4—C5—C6121.41 (19)C10—C11—H11119.635
C1—C6—C5119.75 (19)C12—C11—H11119.641
S2—C8—C9120.77 (14)C11—C12—H12119.913
S2—C8—C13117.72 (14)C13—C12—H12119.912
C9—C8—C13121.50 (18)C8—C13—H13120.669
C8—C9—C10119.07 (18)C12—C13—H13120.677
C9—C10—C11119.86 (19)C14—C15—H14120.818
C10—C11—C12120.7 (2)C16—C15—H14120.817
C11—C12—C13120.18 (19)C15—C16—H15120.052
C8—C13—C12118.65 (18)C17—C16—H15120.052
S2—C14—C15118.40 (15)C16—C17—H16119.551
S2—C14—C19119.46 (14)C18—C17—H16119.556
C15—C14—C19122.13 (17)C17—C18—H17119.844
C14—C15—C16118.37 (19)C19—C18—H17119.842
C15—C16—C17119.90 (19)C14—C19—H18120.805
C16—C17—C18120.9 (2)C18—C19—H18120.818
O1—S1—N1—S2−150.69 (11)S1—C1—C6—C5−174.74 (12)
O1—S1—C1—C2−88.83 (13)C2—C1—C6—C51.6 (3)
O1—S1—C1—C687.52 (13)C6—C1—C2—C3−1.6 (3)
O2—S1—N1—S2−21.45 (14)C1—C2—C3—C40.1 (3)
O2—S1—C1—C2145.64 (12)C2—C3—C4—C51.3 (3)
O2—S1—C1—C6−38.00 (14)C2—C3—C4—C7−178.79 (16)
N1—S1—C1—C224.81 (14)C3—C4—C5—C6−1.3 (3)
N1—S1—C1—C6−158.83 (12)C7—C4—C5—C6178.79 (17)
C1—S1—N1—S295.93 (12)C4—C5—C6—C1−0.2 (3)
N2—S2—N1—S1−25.67 (17)S2—C8—C9—C10−177.44 (11)
N1—S2—C8—C914.99 (14)S2—C8—C13—C12177.35 (11)
N1—S2—C8—C13−163.57 (11)C9—C8—C13—C12−1.2 (3)
C8—S2—N1—S1105.86 (12)C13—C8—C9—C101.1 (3)
N1—S2—C14—C15148.19 (13)C8—C9—C10—C110.0 (3)
N1—S2—C14—C19−31.18 (15)C9—C10—C11—C12−0.9 (3)
C14—S2—N1—S1−144.54 (11)C10—C11—C12—C130.7 (3)
N2—S2—C8—C9153.90 (12)C11—C12—C13—C80.3 (3)
N2—S2—C8—C13−24.66 (14)S2—C14—C15—C16−177.49 (12)
N2—S2—C14—C1515.17 (16)S2—C14—C19—C18177.70 (12)
N2—S2—C14—C19−164.20 (13)C15—C14—C19—C18−1.6 (3)
C8—S2—C14—C15−104.15 (13)C19—C14—C15—C161.9 (3)
C8—S2—C14—C1976.49 (15)C14—C15—C16—C17−1.2 (3)
C14—S2—C8—C9−92.61 (13)C15—C16—C17—C180.3 (4)
C14—S2—C8—C1388.83 (13)C16—C17—C18—C19−0.1 (4)
S1—C1—C2—C3174.68 (11)C17—C18—C19—C140.7 (3)
Symmetry codes: (i) −x, −y+1, −z+2; (ii) x+1, y, z; (iii) −x, y+1/2, −z+3/2; (iv) −x, −y, −z+2; (v) x, −y+1/2, z+1/2; (vi) −x, y−1/2, −z+3/2; (vii) −x+1, −y, −z+2; (viii) x−1, y, z; (ix) x, −y+1/2, z−1/2; (x) −x+1, y+1/2, −z+3/2; (xi) −x+1, y−1/2, −z+3/2; (xii) x+1, y−1, z; (xiii) x−1, y+1, z; (xiv) −x−1, −y+1, −z+2; (xv) −x−1, y+1/2, −z+3/2; (xvi) −x−1, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H8···O2iv0.89 (3)2.20 (3)3.018 (3)152 (2)
C12—H12···O1viii0.952.343.283 (2)169
Symmetry codes: (iv) −x, −y, −z+2; (viii) x−1, y, z.
 

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, for providing facilities for single-crystal X-ray analysis.

Funding information

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

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ISSN: 2414-3146
Volume 4| Part 4| April 2019| x190523
https://doi.org/10.1107/S2414314619005236
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