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

Journal logoIUCrDATA
ISSN: 2414-3146

Dibenzo[2,3:6,7]thiepino[4,5-d][1,2,3]selena­diazole

aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: detert@uni-mainz.de

Edited by M. Weil, Vienna University of Technology, Austria (Received 3 January 2018; accepted 11 January 2018; online 26 January 2018)

Four tetra­cyclic mol­ecules of the title compound, C14H8N2SSe, are present in the asymmetric unit. Their mol­ecular structures are very similar, adopting the shape of a saddle. The selena­diazole moiety of one of the mol­ecules is disordered over two set of sites [occupancy ratio 0.618 (6):0.382 (6)]. In the crystal, layers of mol­ecules with hydrogen surfaces extend parallel to the ab plane and are stacked along the c axis. The crystal studied was refined as an inversion twin.

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

Structure description

1,2,3-Selena­diazo­les are useful precursors for strained cyclo­alkynes (Bissinger et al., 1988[Bissinger, H.-J., Detert, H. & Meier, H. (1988). Liebigs Ann. Chem. pp. 221-224.]; Detert & Meier, 1997[Detert, H. & Meier, H. (1997). Liebigs Ann. Recl, 1997, 1557-1563.]) and heterocycles (Detert et al. 1992[Detert, H., Antony-Mayer, C. & Meier, H. (1992). Angew. Chem. 104, 755-757.]), and are precursors for photochemically induced (Jedináková et al., 2016[Jedináková, P., Šebej, P., Slanina, T., Klán, P. & Hlaváč, J. (2016). Chem. Commun. 52, 4792-4795.]) as well as for strain-accelerated click-reactions (Jewett & Bertozzi, 2010[Jewett, J. C. & Bertozzi, C. R. (2010). Chem. Soc. Rev. 39, 1272-1279.]).

Sixteen mol­ecules, i.e. four sets of four independent mol­ecules, of the title compound fill the unit cell (Z′ = 4). The forms of all four mol­ecules are nearly identical (Fig. 1[link]). Mol­ecule A is nearly identical to mol­ecule B, and mol­ecule D is nearly identical to mol­ecule C. However, mol­ecules A and D are pseudo-mirror images. The selena­diazole moiety of mol­ecule D is disordered over two sets of sites, with the ratio D (major component):E (minor component) being 0.618 (6):0.382 (6). The mol­ecular shape of these tetra­cycles is that of a saddle, with the sulfur atom being the pommel, the selena­diazole moiety the cantle and the benzene rings the flaps. Representative for the nearly identical parts in mol­ecules AE, only details for A are given. The mean planes of the benzene rings are inclined by an angle of 63.7 (7)°. Although the five-membered diphenyl-1,2,3-selena­diazole unit is not symmetrical, the dihedral angles between the mean planes of neighbouring rings are virtually the same: (C1–C6)–selena­diazole: 40.7 (7)° and selena­diazole–(C8–C13): 39.3 (7)°. The C—S—C bond angle at the sulfur atom [99.5 (7)°] is significantly larger than the N—Se—C bond angle of 87.2 (6)°. The latter is close to the corresponding angle in a 3-methyl-1,2,3-selena­diazo­lium salt [89.1 (4)°; Schollmeyer & Detert, 2016[Schollmeyer, D. & Detert, H. (2016). IUCrData, 1, x161950.]].

[Figure 1]
Figure 1
The structures of the four mol­ecules present in the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. The minor disorder component is shown with dashed lines.

In the crystal structure (Fig. 2[link]), the mol­ecules are packed according to their mol­ecular shape, forming layers parallel to the ab plane. These layers have hydrogen surfaces and are stacked along the c axis.

[Figure 2]
Figure 2
The crystal packing in the title compound in a view along the a axis. The four independent mol­ecules are shown in different colours.

Synthesis and crystallization

The title compound was prepared in seven steps from o-phenyl­thio­benzoic acid according to Jílek et al. (1965[Jílek, J. O., Seidlová, V., Svátek, E. & Provita, M. (1965). Monatsh. Chem. 96, 182-207.]) and Lorch & Meier (1981[Lorch, M. & Meier, H. (1981). Chem. Ber. 114, 2382-2391.]). 1H NMR (CDCl3, 400 MHz): 8.17 (dd, 1 H), 7.71 (m, 2 H), 7.53-7.43 (m, 4 H), 7.33 (ddd, 1 H); 77Se NMR (CDCl3, 76.3 MHz, δ SeO2/D2O) = 0 p.p.m.): δ = 257.3 p.p.m. The title compound was recrystallized from chloro­form/2-propanol (1:1, v:v) to give light-yellow crystals; m.p. = 413 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. The two N atoms and the Se atoms of the five membered selenea­diazole ring of mol­ecule D are disordered over two sets of sites with a refined occupancy ratio of 0.618 (6)/0.382 (6). The C—N and N—N bond lengths inside the ring were restrained to be equal. RIGU and EADP instructions were used for the corresponding ring atoms. Refinement as a inversion twin with a BASF value of 0.41 (2) improved the final reliability factor by 0.35%.

Table 1
Experimental details

Crystal data
Chemical formula C14H8N2SSe
Mr 315.24
Crystal system, space group Orthorhombic, Pna21
Temperature (K) 193
a, b, c (Å) 20.8533 (8), 9.9698 (3), 23.4151 (8)
V3) 4868.1 (3)
Z 16
Radiation type Mo Kα
μ (mm−1) 3.24
Crystal size (mm) 0.34 × 0.26 × 0.05
 
Data collection
Diffractometer Stoe IPDS 2T
Absorption correction Integration (X-RED32; Stoe & Cie, 2006[Stoe & Cie (2006). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.406, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections 28240, 12118, 8561
Rint 0.058
(sin θ/λ)max−1) 0.674
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.080, 0.189, 1.16
No. of reflections 12118
No. of parameters 666
No. of restraints 33
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.71, −0.90
Absolute structure Refined as an inversion twin
Absolute structure parameter 0.41 (2)
Computer programs: X-AREA (Stoe & Cie, 2006[Stoe & Cie (2006). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), X-RED32 (Stoe & Cie, 2006[Stoe & Cie (2006). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2017 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA (Stoe & Cie, 2006); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Dibenzo[2,3:6,7]thiepino[4,5-d][1,2,3]selenadiazole top
Crystal data top
C14H8N2SSeDx = 1.721 Mg m3
Mr = 315.24Melting point: 413 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
a = 20.8533 (8) ÅCell parameters from 38903 reflections
b = 9.9698 (3) Åθ = 2.0–28.3°
c = 23.4151 (8) ŵ = 3.24 mm1
V = 4868.1 (3) Å3T = 193 K
Z = 16Plate, light yellow
F(000) = 24960.34 × 0.26 × 0.05 mm
Data collection top
Stoe IPDS 2T
diffractometer
12118 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus8561 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.058
rotation method scansθmax = 28.6°, θmin = 2.0°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2006)
h = 2726
Tmin = 0.406, Tmax = 0.689k = 1113
28240 measured reflectionsl = 3131
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.080 w = 1/[σ2(Fo2) + (0.0335P)2 + 36.2917P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.189(Δ/σ)max < 0.001
S = 1.16Δρmax = 0.71 e Å3
12118 reflectionsΔρmin = 0.90 e Å3
666 parametersAbsolute structure: Refined as an inversion twin
33 restraintsAbsolute structure parameter: 0.41 (2)
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. Refined as a 2-component inversion twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Se1A0.05143 (8)0.45875 (16)0.54238 (7)0.0493 (4)
C1A0.0215 (7)0.5129 (13)0.4230 (7)0.039 (3)
C2A0.0007 (7)0.6410 (15)0.4345 (8)0.047 (4)
H2A0.0129300.6644520.4722500.056*
C3A0.0051 (7)0.7355 (16)0.3911 (8)0.050 (4)
H3A0.0200320.8234790.3991620.061*
C4A0.0123 (8)0.7008 (18)0.3357 (8)0.051 (4)
H4A0.0085400.7649930.3059140.061*
C5A0.0347 (8)0.5754 (16)0.3237 (8)0.050 (4)
H5A0.0470640.5532170.2858570.060*
C6A0.0394 (7)0.4790 (14)0.3672 (7)0.041 (3)
S7A0.07130 (19)0.3183 (4)0.3501 (2)0.0475 (9)
C8A0.0029 (7)0.2171 (14)0.3656 (7)0.042 (3)
C9A0.0228 (7)0.1421 (14)0.3223 (7)0.043 (3)
H9A0.0064550.1502520.2845740.051*
C10A0.0736 (7)0.0529 (15)0.3338 (7)0.044 (4)
H10A0.0929180.0036620.3036040.052*
C11A0.0945 (7)0.0377 (15)0.3879 (7)0.042 (3)
H11A0.1268620.0267690.3957630.051*
C12A0.0701 (7)0.1132 (15)0.4320 (7)0.042 (3)
H12A0.0871090.1043900.4694150.050*
C13A0.0195 (7)0.2044 (14)0.4210 (6)0.037 (3)
C14A0.0083 (6)0.2796 (14)0.4697 (6)0.037 (3)
C15A0.0260 (6)0.4132 (13)0.4687 (7)0.039 (3)
N16A0.0135 (6)0.2135 (13)0.5210 (6)0.044 (3)
N17A0.0339 (7)0.2808 (13)0.5628 (6)0.047 (3)
Se1B0.17948 (8)0.44736 (17)0.03038 (8)0.0527 (4)
C1B0.1465 (7)0.5053 (15)0.0877 (8)0.045 (4)
C2B0.1273 (7)0.6349 (16)0.0762 (8)0.049 (4)
H2B0.1166880.6585400.0380270.058*
C3B0.1230 (8)0.7319 (16)0.1185 (9)0.053 (4)
H3B0.1109840.8208430.1086650.064*
C4B0.1360 (8)0.7010 (18)0.1742 (10)0.057 (5)
H4B0.1325830.7674750.2030780.068*
C5B0.1544 (8)0.5700 (16)0.1880 (7)0.047 (4)
H5B0.1625520.5463710.2266390.056*
C6B0.1607 (7)0.4747 (14)0.1451 (8)0.043 (3)
S7B0.19277 (19)0.3150 (4)0.1643 (2)0.0484 (10)
C8B0.1270 (6)0.2093 (13)0.1468 (7)0.040 (3)
C9B0.1004 (7)0.1329 (16)0.1929 (8)0.045 (4)
H9B0.1148870.1438280.2310840.054*
C10B0.0516 (7)0.0406 (15)0.1788 (7)0.044 (3)
H10B0.0338340.0147070.2077430.053*
C11B0.0290 (7)0.0293 (14)0.1226 (7)0.041 (3)
H11B0.0048450.0309580.1139040.050*
C12B0.0560 (7)0.1054 (15)0.0804 (7)0.042 (3)
H12B0.0407900.0962790.0423790.050*
C13B0.1053 (6)0.1963 (14)0.0918 (7)0.038 (3)
C14B0.1346 (6)0.2741 (13)0.0429 (7)0.037 (3)
C15B0.1516 (7)0.4067 (14)0.0420 (7)0.044 (3)
N16B0.1405 (6)0.2060 (13)0.0067 (6)0.043 (3)
N17B0.1618 (7)0.2679 (14)0.0504 (7)0.054 (3)
Se1C0.33561 (7)0.52544 (15)0.14539 (8)0.0476 (4)
C1C0.2971 (6)0.7737 (14)0.0899 (6)0.037 (3)
C2C0.2950 (7)0.7166 (16)0.0362 (8)0.049 (4)
H2C0.3164410.6338240.0298870.059*
C3C0.2626 (9)0.7764 (18)0.0090 (8)0.057 (5)
H3C0.2605550.7348530.0454330.069*
C4C0.2329 (8)0.9006 (19)0.0013 (8)0.052 (4)
H4C0.2118970.9450200.0293260.063*
C5C0.2333 (7)0.9595 (17)0.0539 (8)0.052 (4)
H5C0.2119901.0426280.0598470.062*
C6C0.2659 (6)0.8952 (14)0.0997 (7)0.038 (3)
S7C0.26504 (17)0.9701 (4)0.16780 (19)0.0461 (9)
C8C0.3469 (7)1.0082 (14)0.1729 (7)0.042 (3)
C9C0.3650 (8)1.1445 (16)0.1751 (7)0.049 (4)
H9C0.3334831.2125730.1706220.058*
C10C0.4289 (9)1.1796 (18)0.1838 (8)0.058 (5)
H10C0.4404481.2714610.1871920.069*
C11C0.4759 (8)1.0817 (18)0.1874 (7)0.052 (4)
H11C0.5196891.1056630.1916880.063*
C12C0.4575 (8)0.9463 (16)0.1848 (7)0.046 (4)
H12C0.4892430.8784140.1882380.055*
C13C0.3940 (7)0.9097 (16)0.1772 (6)0.039 (3)
C14C0.3768 (6)0.7672 (14)0.1725 (7)0.035 (3)
C15C0.3342 (6)0.7100 (14)0.1355 (7)0.040 (3)
N16C0.4114 (6)0.6782 (13)0.2063 (6)0.046 (3)
N17C0.3994 (6)0.5515 (12)0.2006 (6)0.047 (3)
Se1D0.20970 (16)0.5125 (3)0.35682 (17)0.0487 (10)0.618 (6)
Se1E0.2824 (5)0.6295 (9)0.2903 (4)0.051 (2)0.382 (6)
C1D0.1705 (7)0.7708 (14)0.4123 (7)0.040 (3)
C2D0.1656 (8)0.7163 (15)0.4674 (7)0.048 (4)
H2D0.1851030.6322700.4753150.057*
C3D0.1331 (9)0.782 (2)0.5103 (8)0.057 (5)
H3D0.1304910.7431950.5472900.069*
C4D0.1045 (8)0.9034 (18)0.4994 (8)0.054 (4)
H4D0.0818160.9486530.5288630.065*
C5D0.1085 (7)0.9587 (17)0.4466 (8)0.052 (4)
H5D0.0884271.0426900.4397870.062*
C6D0.1414 (7)0.8961 (16)0.4020 (7)0.046 (4)
S7D0.14250 (18)0.9657 (4)0.33250 (19)0.0480 (9)
C8D0.2262 (7)1.0023 (15)0.3266 (7)0.041 (3)
C9D0.2462 (8)1.1366 (18)0.3245 (8)0.051 (4)
H9D0.2159601.2075760.3267460.061*
C10D0.3109 (9)1.1633 (19)0.3193 (8)0.061 (5)
H10D0.3253871.2533170.3161210.073*
C11D0.3537 (8)1.0609 (18)0.3185 (8)0.058 (5)
H11D0.3980421.0822800.3161930.070*
C12D0.3366 (7)0.9281 (18)0.3210 (7)0.048 (4)
H12D0.3681280.8594500.3189230.057*
C13D0.2701 (7)0.8959 (15)0.3268 (7)0.042 (3)
C14D0.2510 (8)0.7555 (15)0.3305 (6)0.040 (3)
C15D0.2079 (7)0.7001 (13)0.3679 (7)0.040 (3)
N16D0.288 (2)0.657 (4)0.299 (2)0.038 (5)0.618 (6)
N17D0.2742 (13)0.532 (3)0.2986 (12)0.059 (5)0.618 (6)
N16E0.204 (2)0.558 (3)0.365 (2)0.038 (5)0.382 (6)
N17E0.239 (2)0.508 (4)0.325 (2)0.059 (5)0.382 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se1A0.0528 (9)0.0437 (8)0.0515 (9)0.0091 (7)0.0088 (8)0.0013 (8)
C1A0.036 (7)0.025 (6)0.057 (9)0.010 (5)0.005 (6)0.002 (6)
C2A0.034 (7)0.035 (8)0.072 (12)0.005 (6)0.013 (7)0.002 (7)
C3A0.037 (8)0.033 (8)0.082 (13)0.001 (6)0.009 (8)0.007 (8)
C4A0.046 (9)0.052 (9)0.055 (11)0.000 (7)0.012 (8)0.020 (8)
C5A0.034 (8)0.045 (9)0.071 (12)0.011 (7)0.001 (8)0.000 (8)
C6A0.035 (7)0.036 (7)0.050 (9)0.002 (6)0.001 (6)0.001 (7)
S7A0.040 (2)0.042 (2)0.061 (3)0.0016 (16)0.0106 (19)0.0024 (19)
C8A0.044 (8)0.037 (7)0.046 (8)0.007 (6)0.002 (7)0.000 (7)
C9A0.044 (8)0.032 (7)0.051 (9)0.006 (6)0.008 (7)0.001 (6)
C10A0.037 (7)0.040 (8)0.054 (9)0.004 (6)0.014 (7)0.011 (7)
C11A0.031 (7)0.038 (7)0.058 (9)0.001 (6)0.001 (6)0.011 (7)
C12A0.039 (8)0.037 (8)0.049 (9)0.001 (6)0.007 (7)0.001 (7)
C13A0.034 (7)0.030 (7)0.048 (9)0.004 (5)0.002 (6)0.003 (6)
C14A0.034 (7)0.038 (7)0.040 (7)0.003 (5)0.000 (6)0.005 (7)
C15A0.036 (7)0.036 (7)0.045 (8)0.002 (5)0.006 (6)0.004 (7)
N16A0.040 (7)0.048 (7)0.045 (7)0.002 (6)0.003 (6)0.001 (6)
N17A0.043 (7)0.047 (7)0.051 (8)0.004 (6)0.005 (6)0.001 (6)
Se1B0.0546 (9)0.0460 (8)0.0576 (10)0.0042 (7)0.0079 (8)0.0039 (8)
C1B0.032 (7)0.040 (8)0.062 (10)0.007 (6)0.001 (7)0.000 (7)
C2B0.047 (9)0.041 (8)0.058 (11)0.005 (7)0.001 (8)0.002 (7)
C3B0.042 (9)0.030 (7)0.088 (13)0.006 (6)0.007 (9)0.015 (8)
C4B0.043 (9)0.042 (9)0.086 (14)0.007 (7)0.005 (9)0.013 (9)
C5B0.049 (9)0.044 (8)0.048 (9)0.006 (7)0.003 (7)0.011 (7)
C6B0.031 (6)0.041 (7)0.057 (9)0.008 (6)0.002 (7)0.002 (8)
S7B0.0357 (18)0.041 (2)0.068 (3)0.0033 (15)0.0106 (18)0.0054 (18)
C8B0.028 (6)0.032 (6)0.061 (9)0.009 (5)0.009 (7)0.005 (7)
C9B0.032 (7)0.049 (9)0.054 (10)0.000 (6)0.001 (7)0.003 (7)
C10B0.037 (8)0.039 (8)0.056 (10)0.003 (6)0.008 (7)0.007 (7)
C11B0.030 (7)0.030 (7)0.064 (10)0.004 (5)0.008 (7)0.003 (7)
C12B0.029 (7)0.045 (8)0.052 (9)0.002 (6)0.001 (6)0.005 (7)
C13B0.030 (7)0.030 (7)0.055 (9)0.003 (5)0.003 (6)0.000 (6)
C14B0.028 (6)0.034 (7)0.048 (8)0.000 (5)0.004 (6)0.001 (7)
C15B0.041 (8)0.032 (7)0.058 (9)0.011 (6)0.007 (7)0.008 (7)
N16B0.030 (6)0.047 (7)0.053 (8)0.003 (5)0.001 (6)0.001 (6)
N17B0.045 (7)0.049 (8)0.068 (9)0.005 (6)0.002 (7)0.004 (7)
Se1C0.0406 (8)0.0325 (6)0.0695 (10)0.0016 (6)0.0008 (8)0.0042 (8)
C1C0.023 (6)0.036 (7)0.052 (9)0.004 (5)0.004 (6)0.009 (6)
C2C0.040 (8)0.043 (8)0.064 (11)0.006 (6)0.009 (7)0.006 (8)
C3C0.066 (12)0.054 (10)0.052 (10)0.011 (9)0.009 (9)0.000 (8)
C4C0.036 (8)0.066 (11)0.055 (10)0.003 (7)0.012 (7)0.011 (9)
C5C0.025 (7)0.054 (10)0.078 (13)0.006 (6)0.009 (7)0.001 (9)
C6C0.025 (7)0.037 (7)0.051 (9)0.006 (5)0.005 (6)0.006 (6)
S7C0.0301 (17)0.042 (2)0.066 (3)0.0062 (14)0.0034 (16)0.0021 (18)
C8C0.039 (7)0.030 (7)0.059 (9)0.002 (6)0.000 (7)0.005 (6)
C9C0.045 (9)0.044 (9)0.057 (10)0.006 (7)0.002 (7)0.001 (7)
C10C0.055 (10)0.047 (9)0.071 (12)0.015 (8)0.008 (9)0.004 (9)
C11C0.046 (9)0.055 (10)0.057 (10)0.011 (7)0.001 (8)0.003 (8)
C12C0.041 (8)0.048 (9)0.049 (9)0.002 (7)0.002 (7)0.002 (7)
C13C0.034 (7)0.048 (8)0.037 (8)0.008 (6)0.002 (6)0.003 (7)
C14C0.022 (6)0.036 (7)0.047 (8)0.005 (5)0.001 (6)0.004 (6)
C15C0.026 (6)0.042 (7)0.051 (9)0.004 (5)0.001 (6)0.004 (7)
N16C0.043 (7)0.046 (7)0.050 (8)0.007 (6)0.005 (6)0.009 (6)
N17C0.033 (6)0.038 (7)0.070 (9)0.009 (5)0.003 (6)0.009 (6)
Se1D0.0419 (17)0.0320 (14)0.072 (2)0.0013 (13)0.0030 (14)0.0002 (15)
Se1E0.038 (3)0.060 (6)0.054 (4)0.008 (3)0.001 (3)0.015 (3)
C1D0.034 (7)0.032 (7)0.055 (9)0.003 (5)0.002 (7)0.002 (6)
C2D0.056 (10)0.040 (8)0.047 (9)0.007 (7)0.000 (8)0.001 (7)
C3D0.053 (11)0.070 (12)0.049 (10)0.013 (9)0.002 (8)0.010 (9)
C4D0.034 (8)0.060 (11)0.067 (12)0.014 (7)0.008 (8)0.013 (9)
C5D0.039 (8)0.044 (9)0.072 (11)0.009 (7)0.003 (8)0.020 (8)
C6D0.030 (7)0.042 (8)0.065 (11)0.002 (6)0.005 (7)0.007 (7)
S7D0.0354 (19)0.046 (2)0.063 (3)0.0019 (16)0.0041 (17)0.0098 (19)
C8D0.043 (8)0.041 (8)0.040 (8)0.016 (6)0.000 (6)0.000 (6)
C9D0.049 (9)0.046 (9)0.059 (10)0.001 (7)0.002 (8)0.001 (8)
C10D0.057 (11)0.056 (11)0.070 (12)0.024 (9)0.010 (9)0.004 (9)
C11D0.040 (9)0.059 (11)0.076 (12)0.014 (8)0.004 (8)0.001 (9)
C12D0.030 (7)0.063 (10)0.050 (9)0.004 (7)0.000 (7)0.001 (8)
C13D0.035 (7)0.039 (8)0.052 (9)0.003 (6)0.002 (7)0.004 (7)
C14D0.043 (8)0.035 (7)0.041 (8)0.000 (6)0.002 (6)0.004 (6)
C15D0.036 (7)0.029 (6)0.054 (9)0.000 (5)0.008 (6)0.002 (6)
N16D0.029 (10)0.034 (8)0.050 (13)0.000 (7)0.013 (8)0.005 (9)
N17D0.059 (13)0.039 (8)0.078 (14)0.002 (8)0.006 (8)0.009 (8)
N16E0.029 (10)0.034 (8)0.050 (13)0.000 (7)0.013 (8)0.005 (9)
N17E0.059 (13)0.039 (8)0.078 (14)0.002 (8)0.006 (8)0.009 (8)
Geometric parameters (Å, º) top
Se1A—C15A1.862 (16)C1C—C2C1.38 (2)
Se1A—N17A1.874 (13)C1C—C6C1.39 (2)
C1A—C2A1.384 (19)C1C—C15C1.462 (19)
C1A—C6A1.40 (2)C2C—C3C1.39 (2)
C1A—C15A1.46 (2)C2C—H2C0.9500
C2A—C3A1.39 (2)C3C—C4C1.41 (2)
C2A—H2A0.9500C3C—H3C0.9500
C3A—C4A1.39 (2)C4C—C5C1.36 (3)
C3A—H3A0.9500C4C—H4C0.9500
C4A—C5A1.36 (2)C5C—C6C1.42 (2)
C4A—H4A0.9500C5C—H5C0.9500
C5A—C6A1.40 (2)C6C—S7C1.760 (16)
C5A—H5A0.9500S7C—C8C1.753 (15)
C6A—S7A1.779 (15)C8C—C13C1.39 (2)
S7A—C8A1.785 (16)C8C—C9C1.41 (2)
C8A—C9A1.37 (2)C9C—C10C1.39 (2)
C8A—C13A1.38 (2)C9C—H9C0.9500
C9A—C10A1.41 (2)C10C—C11C1.38 (2)
C9A—H9A0.9500C10C—H10C0.9500
C10A—C11A1.35 (2)C11C—C12C1.40 (2)
C10A—H10A0.9500C11C—H11C0.9500
C11A—C12A1.37 (2)C12C—C13C1.39 (2)
C11A—H11A0.9500C12C—H12C0.9500
C12A—C13A1.42 (2)C13C—C14C1.47 (2)
C12A—H12A0.9500C14C—C15C1.366 (19)
C13A—C14A1.48 (2)C14C—N16C1.390 (18)
C14A—N16A1.373 (18)N16C—N17C1.294 (17)
C14A—C15A1.383 (18)Se1D—C15D1.889 (14)
N16A—N17A1.262 (18)Se1D—N17D1.93 (3)
Se1B—C15B1.836 (17)Se1E—C14D1.700 (17)
Se1B—N17B1.885 (14)Se1E—N17E1.72 (5)
C1B—C2B1.38 (2)C1D—C2D1.40 (2)
C1B—C6B1.41 (2)C1D—C6D1.41 (2)
C1B—C15B1.46 (2)C1D—C15D1.48 (2)
C2B—C3B1.39 (2)C2D—C3D1.37 (2)
C2B—H2B0.9500C2D—H2D0.9500
C3B—C4B1.37 (3)C3D—C4D1.38 (3)
C3B—H3B0.9500C3D—H3D0.9500
C4B—C5B1.40 (2)C4D—C5D1.36 (2)
C4B—H4B0.9500C4D—H4D0.9500
C5B—C6B1.39 (2)C5D—C6D1.40 (2)
C5B—H5B0.9500C5D—H5D0.9500
C6B—S7B1.783 (16)C6D—S7D1.770 (17)
S7B—C8B1.777 (14)S7D—C8D1.787 (15)
C8B—C13B1.37 (2)C8D—C13D1.40 (2)
C8B—C9B1.43 (2)C8D—C9D1.40 (2)
C9B—C10B1.41 (2)C9D—C10D1.38 (2)
C9B—H9B0.9500C9D—H9D0.9500
C10B—C11B1.40 (2)C10D—C11D1.36 (3)
C10B—H10B0.9500C10D—H10D0.9500
C11B—C12B1.37 (2)C11D—C12D1.37 (2)
C11B—H11B0.9500C11D—H11D0.9500
C12B—C13B1.40 (2)C12D—C13D1.43 (2)
C12B—H12B0.9500C12D—H12D0.9500
C13B—C14B1.51 (2)C13D—C14D1.46 (2)
C14B—N16B1.35 (2)C14D—C15D1.37 (2)
C14B—C15B1.369 (19)C14D—N16D1.45 (4)
N16B—N17B1.273 (19)C15D—N16E1.42 (3)
Se1C—C15C1.855 (15)N16D—N17D1.28 (4)
Se1C—N17C1.874 (14)N16E—N17E1.28 (4)
C15A—Se1A—N17A87.2 (6)C1C—C2C—C3C122.1 (15)
C2A—C1A—C6A119.5 (14)C1C—C2C—H2C118.9
C2A—C1A—C15A120.5 (15)C3C—C2C—H2C118.9
C6A—C1A—C15A120.0 (12)C2C—C3C—C4C117.5 (17)
C1A—C2A—C3A120.4 (17)C2C—C3C—H3C121.2
C1A—C2A—H2A119.8C4C—C3C—H3C121.2
C3A—C2A—H2A119.8C5C—C4C—C3C122.1 (17)
C2A—C3A—C4A119.8 (16)C5C—C4C—H4C118.9
C2A—C3A—H3A120.1C3C—C4C—H4C118.9
C4A—C3A—H3A120.1C4C—C5C—C6C119.3 (16)
C5A—C4A—C3A120.6 (16)C4C—C5C—H5C120.3
C5A—C4A—H4A119.7C6C—C5C—H5C120.3
C3A—C4A—H4A119.7C1C—C6C—C5C119.4 (15)
C4A—C5A—C6A120.2 (17)C1C—C6C—S7C121.5 (11)
C4A—C5A—H5A119.9C5C—C6C—S7C119.1 (12)
C6A—C5A—H5A119.9C8C—S7C—C6C98.3 (7)
C1A—C6A—C5A119.5 (14)C13C—C8C—C9C119.2 (14)
C1A—C6A—S7A121.7 (11)C13C—C8C—S7C122.6 (11)
C5A—C6A—S7A118.8 (13)C9C—C8C—S7C118.1 (11)
C6A—S7A—C8A99.5 (7)C10C—C9C—C8C120.2 (16)
C9A—C8A—C13A120.9 (15)C10C—C9C—H9C119.9
C9A—C8A—S7A118.1 (12)C8C—C9C—H9C119.9
C13A—C8A—S7A120.8 (12)C11C—C10C—C9C120.5 (16)
C8A—C9A—C10A119.8 (15)C11C—C10C—H10C119.7
C8A—C9A—H9A120.1C9C—C10C—H10C119.7
C10A—C9A—H9A120.1C10C—C11C—C12C118.8 (15)
C11A—C10A—C9A119.6 (14)C10C—C11C—H11C120.6
C11A—C10A—H10A120.2C12C—C11C—H11C120.6
C9A—C10A—H10A120.2C13C—C12C—C11C121.3 (16)
C10A—C11A—C12A121.6 (14)C13C—C12C—H12C119.4
C10A—C11A—H11A119.2C11C—C12C—H12C119.4
C12A—C11A—H11A119.2C12C—C13C—C8C119.9 (14)
C11A—C12A—C13A119.4 (14)C12C—C13C—C14C119.7 (14)
C11A—C12A—H12A120.3C8C—C13C—C14C120.3 (13)
C13A—C12A—H12A120.3C15C—C14C—N16C115.6 (13)
C8A—C13A—C12A118.7 (14)C15C—C14C—C13C127.6 (14)
C8A—C13A—C14A123.0 (13)N16C—C14C—C13C116.7 (13)
C12A—C13A—C14A118.4 (13)C14C—C15C—C1C128.7 (14)
N16A—C14A—C15A117.2 (14)C14C—C15C—Se1C108.9 (11)
N16A—C14A—C13A117.5 (12)C1C—C15C—Se1C122.1 (10)
C15A—C14A—C13A125.3 (14)N17C—N16C—C14C117.7 (13)
C14A—C15A—C1A130.6 (15)N16C—N17C—Se1C110.0 (10)
C14A—C15A—Se1A107.1 (11)C15D—Se1D—N17D90.6 (9)
C1A—C15A—Se1A122.0 (10)C14D—Se1E—N17E92.9 (15)
N17A—N16A—C14A116.8 (13)C2D—C1D—C6D117.9 (14)
N16A—N17A—Se1A111.8 (11)C2D—C1D—C15D120.0 (13)
C15B—Se1B—N17B87.6 (7)C6D—C1D—C15D122.0 (14)
C2B—C1B—C6B116.8 (15)C3D—C2D—C1D121.5 (16)
C2B—C1B—C15B120.6 (15)C3D—C2D—H2D119.2
C6B—C1B—C15B122.6 (14)C1D—C2D—H2D119.2
C1B—C2B—C3B122.1 (17)C2D—C3D—C4D119.8 (17)
C1B—C2B—H2B119.0C2D—C3D—H3D120.1
C3B—C2B—H2B119.0C4D—C3D—H3D120.1
C4B—C3B—C2B120.8 (16)C5D—C4D—C3D120.0 (17)
C4B—C3B—H3B119.6C5D—C4D—H4D120.0
C2B—C3B—H3B119.6C3D—C4D—H4D120.0
C3B—C4B—C5B119.1 (17)C4D—C5D—C6D122.0 (16)
C3B—C4B—H4B120.5C4D—C5D—H5D119.0
C5B—C4B—H4B120.5C6D—C5D—H5D119.0
C6B—C5B—C4B119.8 (17)C5D—C6D—C1D118.7 (16)
C6B—C5B—H5B120.1C5D—C6D—S7D121.2 (13)
C4B—C5B—H5B120.1C1D—C6D—S7D119.9 (12)
C5B—C6B—C1B121.4 (15)C6D—S7D—C8D99.4 (7)
C5B—C6B—S7B117.7 (14)C13D—C8D—C9D121.8 (14)
C1B—C6B—S7B120.8 (12)C13D—C8D—S7D118.9 (11)
C8B—S7B—C6B100.5 (6)C9D—C8D—S7D119.2 (13)
C13B—C8B—C9B122.0 (13)C10D—C9D—C8D118.6 (16)
C13B—C8B—S7B121.7 (12)C10D—C9D—H9D120.7
C9B—C8B—S7B116.2 (12)C8D—C9D—H9D120.7
C10B—C9B—C8B116.7 (15)C11D—C10D—C9D119.9 (17)
C10B—C9B—H9B121.7C11D—C10D—H10D120.0
C8B—C9B—H9B121.7C9D—C10D—H10D120.0
C11B—C10B—C9B121.0 (14)C10D—C11D—C12D123.7 (16)
C11B—C10B—H10B119.5C10D—C11D—H11D118.2
C9B—C10B—H10B119.5C12D—C11D—H11D118.2
C12B—C11B—C10B119.7 (13)C11D—C12D—C13D118.2 (16)
C12B—C11B—H11B120.1C11D—C12D—H12D120.9
C10B—C11B—H11B120.1C13D—C12D—H12D120.9
C11B—C12B—C13B121.7 (15)C8D—C13D—C12D117.6 (14)
C11B—C12B—H12B119.2C8D—C13D—C14D123.3 (13)
C13B—C12B—H12B119.2C12D—C13D—C14D119.1 (14)
C8B—C13B—C12B118.9 (14)C15D—C14D—N16D114 (2)
C8B—C13B—C14B122.0 (13)C15D—C14D—C13D127.1 (14)
C12B—C13B—C14B119.1 (14)N16D—C14D—C13D118 (2)
N16B—C14B—C15B116.6 (15)C15D—C14D—Se1E108.0 (11)
N16B—C14B—C13B115.5 (12)C13D—C14D—Se1E124.9 (12)
C15B—C14B—C13B127.7 (15)C14D—C15D—N16E115 (2)
C14B—C15B—C1B128.4 (16)C14D—C15D—C1D127.1 (13)
C14B—C15B—Se1B108.0 (12)N16E—C15D—C1D118 (2)
C1B—C15B—Se1B123.5 (11)C14D—C15D—Se1D107.3 (11)
N17B—N16B—C14B118.6 (13)C1D—C15D—Se1D125.4 (11)
N16B—N17B—Se1B109.2 (11)N17D—N16D—C14D123 (4)
C15C—Se1C—N17C87.7 (6)N16D—N17D—Se1D104 (3)
C2C—C1C—C6C119.5 (13)N17E—N16E—C15D112 (3)
C2C—C1C—C15C120.1 (13)N16E—N17E—Se1E112 (3)
C6C—C1C—C15C120.3 (14)
C6A—C1A—C2A—C3A0 (2)C15C—C1C—C6C—C5C176.2 (13)
C15A—C1A—C2A—C3A179.8 (14)C2C—C1C—C6C—S7C178.2 (11)
C1A—C2A—C3A—C4A1 (2)C15C—C1C—C6C—S7C4.6 (18)
C2A—C3A—C4A—C5A1 (2)C4C—C5C—C6C—C1C0 (2)
C3A—C4A—C5A—C6A1 (3)C4C—C5C—C6C—S7C178.9 (12)
C2A—C1A—C6A—C5A0 (2)C1C—C6C—S7C—C8C67.0 (12)
C15A—C1A—C6A—C5A179.7 (14)C5C—C6C—S7C—C8C113.8 (12)
C2A—C1A—C6A—S7A177.5 (11)C6C—S7C—C8C—C13C67.5 (15)
C15A—C1A—C6A—S7A3 (2)C6C—S7C—C8C—C9C115.2 (14)
C4A—C5A—C6A—C1A0 (2)C13C—C8C—C9C—C10C3 (3)
C4A—C5A—C6A—S7A178.0 (12)S7C—C8C—C9C—C10C174.8 (14)
C1A—C6A—S7A—C8A65.1 (14)C8C—C9C—C10C—C11C3 (3)
C5A—C6A—S7A—C8A117.4 (13)C9C—C10C—C11C—C12C3 (3)
C6A—S7A—C8A—C9A119.9 (12)C10C—C11C—C12C—C13C2 (3)
C6A—S7A—C8A—C13A66.5 (13)C11C—C12C—C13C—C8C1 (2)
C13A—C8A—C9A—C10A1 (2)C11C—C12C—C13C—C14C177.8 (15)
S7A—C8A—C9A—C10A175.0 (11)C9C—C8C—C13C—C12C1 (2)
C8A—C9A—C10A—C11A3 (2)S7C—C8C—C13C—C12C175.8 (13)
C9A—C10A—C11A—C12A4 (2)C9C—C8C—C13C—C14C177.3 (15)
C10A—C11A—C12A—C13A3 (2)S7C—C8C—C13C—C14C5 (2)
C9A—C8A—C13A—C12A1 (2)C12C—C13C—C14C—C15C138.0 (16)
S7A—C8A—C13A—C12A174.2 (11)C8C—C13C—C14C—C15C41 (2)
C9A—C8A—C13A—C14A177.7 (13)C12C—C13C—C14C—N16C37 (2)
S7A—C8A—C13A—C14A4.3 (19)C8C—C13C—C14C—N16C144.7 (14)
C11A—C12A—C13A—C8A2 (2)N16C—C14C—C15C—C1C171.6 (14)
C11A—C12A—C13A—C14A176.9 (13)C13C—C14C—C15C—C1C3 (3)
C8A—C13A—C14A—N16A141.8 (14)N16C—C14C—C15C—Se1C1.8 (16)
C12A—C13A—C14A—N16A36.7 (19)C13C—C14C—C15C—Se1C176.4 (12)
C8A—C13A—C14A—C15A42 (2)C2C—C1C—C15C—C14C132.5 (17)
C12A—C13A—C14A—C15A139.5 (15)C6C—C1C—C15C—C14C45 (2)
N16A—C14A—C15A—C1A174.6 (14)C2C—C1C—C15C—Se1C40.2 (18)
C13A—C14A—C15A—C1A2 (2)C6C—C1C—C15C—Se1C142.6 (12)
N16A—C14A—C15A—Se1A0.6 (16)N17C—Se1C—C15C—C14C1.4 (11)
C13A—C14A—C15A—Se1A175.5 (11)N17C—Se1C—C15C—C1C172.5 (12)
C2A—C1A—C15A—C14A135.4 (16)C15C—C14C—N16C—N17C1 (2)
C6A—C1A—C15A—C14A44 (2)C13C—C14C—N16C—N17C176.5 (13)
C2A—C1A—C15A—Se1A37.8 (19)C14C—N16C—N17C—Se1C0.1 (16)
C6A—C1A—C15A—Se1A142.5 (12)C15C—Se1C—N17C—N16C0.8 (11)
N17A—Se1A—C15A—C14A0.6 (10)C6D—C1D—C2D—C3D1 (2)
N17A—Se1A—C15A—C1A175.3 (12)C15D—C1D—C2D—C3D177.6 (15)
C15A—C14A—N16A—N17A0 (2)C1D—C2D—C3D—C4D0 (3)
C13A—C14A—N16A—N17A176.3 (13)C2D—C3D—C4D—C5D0 (3)
C14A—N16A—N17A—Se1A0.4 (17)C3D—C4D—C5D—C6D0 (3)
C15A—Se1A—N17A—N16A0.6 (11)C4D—C5D—C6D—C1D1 (2)
C6B—C1B—C2B—C3B1 (2)C4D—C5D—C6D—S7D176.6 (13)
C15B—C1B—C2B—C3B178.8 (15)C2D—C1D—C6D—C5D1 (2)
C1B—C2B—C3B—C4B2 (3)C15D—C1D—C6D—C5D178.0 (13)
C2B—C3B—C4B—C5B1 (3)C2D—C1D—C6D—S7D176.8 (11)
C3B—C4B—C5B—C6B2 (2)C15D—C1D—C6D—S7D6 (2)
C4B—C5B—C6B—C1B3 (2)C5D—C6D—S7D—C8D115.3 (13)
C4B—C5B—C6B—S7B173.2 (12)C1D—C6D—S7D—C8D69.0 (13)
C2B—C1B—C6B—C5B1 (2)C6D—S7D—C8D—C13D64.6 (14)
C15B—C1B—C6B—C5B179.0 (14)C6D—S7D—C8D—C9D112.5 (14)
C2B—C1B—C6B—S7B174.3 (11)C13D—C8D—C9D—C10D4 (3)
C15B—C1B—C6B—S7B5 (2)S7D—C8D—C9D—C10D179.2 (14)
C5B—C6B—S7B—C8B118.4 (12)C8D—C9D—C10D—C11D3 (3)
C1B—C6B—S7B—C8B65.9 (14)C9D—C10D—C11D—C12D2 (3)
C6B—S7B—C8B—C13B63.7 (13)C10D—C11D—C12D—C13D2 (3)
C6B—S7B—C8B—C9B119.8 (12)C9D—C8D—C13D—C12D4 (2)
C13B—C8B—C9B—C10B1 (2)S7D—C8D—C13D—C12D178.9 (12)
S7B—C8B—C9B—C10B175.0 (11)C9D—C8D—C13D—C14D178.3 (15)
C8B—C9B—C10B—C11B2 (2)S7D—C8D—C13D—C14D1 (2)
C9B—C10B—C11B—C12B2 (2)C11D—C12D—C13D—C8D3 (2)
C10B—C11B—C12B—C13B1 (2)C11D—C12D—C13D—C14D179.0 (16)
C9B—C8B—C13B—C12B0 (2)C8D—C13D—C14D—C15D47 (2)
S7B—C8B—C13B—C12B176.1 (10)C12D—C13D—C14D—C15D135.1 (17)
C9B—C8B—C13B—C14B178.2 (13)C8D—C13D—C14D—N16D144 (3)
S7B—C8B—C13B—C14B1.9 (18)C12D—C13D—C14D—N16D33 (3)
C11B—C12B—C13B—C8B0 (2)C8D—C13D—C14D—Se1E136.2 (15)
C11B—C12B—C13B—C14B177.9 (13)C12D—C13D—C14D—Se1E41 (2)
C8B—C13B—C14B—N16B141.3 (13)N17E—Se1E—C14D—C15D1.0 (19)
C12B—C13B—C14B—N16B36.7 (18)N17E—Se1E—C14D—C13D176.0 (19)
C8B—C13B—C14B—C15B44 (2)C13D—C14D—C15D—N16E174 (2)
C12B—C13B—C14B—C15B138.5 (16)Se1E—C14D—C15D—N16E3 (3)
N16B—C14B—C15B—C1B175.8 (14)N16D—C14D—C15D—C1D170 (3)
C13B—C14B—C15B—C1B1 (3)C13D—C14D—C15D—C1D1 (3)
N16B—C14B—C15B—Se1B1.0 (16)Se1E—C14D—C15D—C1D178.0 (13)
C13B—C14B—C15B—Se1B176.1 (11)N16D—C14D—C15D—Se1D5 (3)
C2B—C1B—C15B—C14B139.9 (16)C13D—C14D—C15D—Se1D174.3 (13)
C6B—C1B—C15B—C14B40 (2)C2D—C1D—C15D—C14D135.1 (17)
C2B—C1B—C15B—Se1B36 (2)C6D—C1D—C15D—C14D42 (2)
C6B—C1B—C15B—Se1B143.4 (12)C2D—C1D—C15D—N16E40 (3)
N17B—Se1B—C15B—C14B0.7 (11)C6D—C1D—C15D—N16E143 (2)
N17B—Se1B—C15B—C1B176.2 (13)C2D—C1D—C15D—Se1D39 (2)
C15B—C14B—N16B—N17B1 (2)C6D—C1D—C15D—Se1D143.6 (13)
C13B—C14B—N16B—N17B176.5 (13)N17D—Se1D—C15D—C14D0.5 (13)
C14B—N16B—N17B—Se1B0.0 (16)N17D—Se1D—C15D—C1D175.0 (14)
C15B—Se1B—N17B—N16B0.4 (11)C15D—C14D—N16D—N17D12 (6)
C6C—C1C—C2C—C3C0 (2)C13D—C14D—N16D—N17D179 (4)
C15C—C1C—C2C—C3C177.3 (15)C14D—N16D—N17D—Se1D10 (5)
C1C—C2C—C3C—C4C2 (3)C14D—C15D—N16E—N17E4 (5)
C2C—C3C—C4C—C5C2 (3)C1D—C15D—N16E—N17E179 (3)
C3C—C4C—C5C—C6C1 (2)C15D—N16E—N17E—Se1E3 (5)
C2C—C1C—C6C—C5C1 (2)C14D—Se1E—N17E—N16E1 (4)
 

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