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

Journal logoIUCrDATA
ISSN: 2414-3146

3-Methyl-4,5,6,7,8,9-hexa­hydro­cyclo­octeno-1,2,3-selena­diazo­lium iodide–tri­chloro­methane (4/1)

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

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 26 January 2017; accepted 31 January 2017; online 3 February 2017)

The title solvated salt, 4C9H15N2Se+·4I·CHCl3, co-crystallizes with chloro­form. The asymmetric unit contains four very similar ion pairs and one solvent mol­ecule. In the crystal, layers of parallel chloro­form-filled channels formed by two different ion pairs alternate with layers formed by the other two ion pairs. Disorder is observed for some C and H atoms in two of the cations with occupancy ratios of 0.68:0.32 and 0.62:0.38.

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.]). Cyclo­octeno-1,2,3-selena­diazole, first prepared by Meier & Voigt (1972[Meier, H. & Voigt, E. (1972). Tetrahedron, 28, 187-198.]), reacts with iodo­methane to yield the 3-methyl-substituted selena­diazo­lium iodide. Crystals with this cation have been obtained with a 2/1 mixture of iodide and triiodide anions (Schollmeyer & Detert, 2016[Schollmeyer, D. & Detert, H. (2016). IUCrData, 1, x161950.]). Here, the only anion is iodide, but the compound co-crystallizes with 1/4 chloro­form mol­ecules per ion pair. The mol­ecular geometries of the cations reported here and in the previous article are nearly identical.

The asymmetric unit (Fig. 1[link]) is composed of four slightly different ion pairs of the title compound and one chloro­form mol­ecule. The cations A, B, and C are very similar, differing from cation D. All cations adopt an L-type shape, but the conformation at C6—C7 of the hexa­methyl­ene tether is inverted in D. All heterocyclic rings are identical, with a maximum deviation of 0.02 Å at N2(A) from the mean plane.

[Figure 1]
Figure 1
Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level.

In all ion pairs, the shortest distance between the iodide and the cation is to atom N2 of the selena­diazo­lium ring: N2A⋯I2 = 3.869 (9) Å, N2B ⋯I1= 3.287 (9) Å, N2C⋯I3 = 3.754 (8) Å and N2D⋯I4 = 3.768 (9) Å. Only N1C has a comparable distance to the next iodide: N1C⋯I3 = 3.784 (9) Å. The shortest spacing between iodide ions are I1⋯I4 = 6.042 (1) Å and I4⋯I4 = 5.940 (2) Å.

The packing of the mol­ecules is quite complex (Fig. 2[link]). A channel along the a-axis direction is composed of two mol­ecules each of B and D, connected via a center of symmetry. The channel is filled with chloro­form mol­ecules forming the spindle of a spiral stair. The steps are represented by alternating cations and iodide ions. These channels are arranged in layers parallel to the b axis. Along the c axis, layers of the channels alternate with layers of `inverted' channels formed from two A and two B mol­ecules.

[Figure 2]
Figure 2
Partial packing diagram. View along (100). The symmetry-independent entities are drawn with different colours.

Synthesis and crystallization

The title compound was prepared from cyclo­octeno-1,2,3-selena­diazole (Meier & Voigt, 1972[Meier, H. & Voigt, E. (1972). Tetrahedron, 28, 187-198.]) and methyl iodide as reported by us (Schollmeyer & Detert, 2016[Schollmeyer, D. & Detert, H. (2016). IUCrData, 1, x161950.]). Chromatographic purification followed by recrystallization from chloro­form yielded brownish crystals with m.p. 471 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. The s.o.f. for the disordered carbon atoms in mol­ecules A and D were kept fixed, while the anisotropic displacement parameters were restrained using the RIGU instruction.

Table 1
Experimental details

Crystal data
Chemical formula 4C9H15N2Se+·4I·CHCl3
Mr 1547.73
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 295
a, b, c (Å) 10.5250 (9), 13.4368 (9), 20.112 (2)
α, β, γ (°) 71.141 (8), 89.472 (9), 76.460 (6)
V3) 2609.9 (4)
Z 2
Radiation type Cu Kα
μ (mm−1) 23.62
Crystal size (mm) 0.56 × 0.32 × 0.12
 
Data collection
Diffractometer Enraf–Nonius CAD-4
Absorption correction Numerical (PLATON; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.])
Tmin, Tmax 0.006, 0.202
No. of measured, independent and observed [I > 2σ(I)] reflections 11193, 10589, 7331
Rint 0.067
(sin θ/λ)max−1) 0.623
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.197, 1.05
No. of reflections 10589
No. of parameters 542
No. of restraints 75
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.84, −1.19
Computer programs: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]), CORINC (Dräger & Gattow, 1971[Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.]), SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]), SHELXL2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009).

3-Methyl-4,5,6,7,8,9-hexahydrocycloocteno-1,2,3-selenadiazolium iodide–trichloromethane (4/1) top
Crystal data top
4C9H15N2Se+·4I·CHCl3Z = 2
Mr = 1547.73F(000) = 1476
Triclinic, P1Dx = 1.969 Mg m3
a = 10.5250 (9) ÅCu Kα radiation, λ = 1.54178 Å
b = 13.4368 (9) ÅCell parameters from 25 reflections
c = 20.112 (2) Åθ = 24–38°
α = 71.141 (8)°µ = 23.62 mm1
β = 89.472 (9)°T = 295 K
γ = 76.460 (6)°Plate, yellow
V = 2609.9 (4) Å30.56 × 0.32 × 0.12 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
7331 reflections with I > 2σ(I)
Radiation source: Rotating anodeRint = 0.067
ω/2θ scanθmax = 74.0°, θmin = 2.3°
Absorption correction: numerical
(PLATON; Spek, 2009)
h = 130
Tmin = 0.006, Tmax = 0.202k = 1616
11193 measured reflectionsl = 2525
10589 independent reflections3 standard reflections every 60 min
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.067 w = 1/[σ2(Fo2) + (0.1024P)2 + 1.7825P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.197(Δ/σ)max = 0.001
S = 1.05Δρmax = 1.84 e Å3
10589 reflectionsΔρmin = 1.19 e Å3
542 parametersExtinction correction: SHELXL2014 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
75 restraintsExtinction coefficient: 0.00067 (6)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Se1A0.54844 (11)0.41276 (9)0.09780 (5)0.0497 (3)
N1A0.3841 (9)0.4588 (7)0.1214 (4)0.0498 (19)
N2A0.3060 (8)0.4144 (6)0.0971 (4)0.0413 (16)
C3A0.3520 (9)0.3509 (8)0.0564 (4)0.041 (2)
C4A0.2640 (10)0.3023 (9)0.0257 (5)0.049 (2)
H4A10.29110.30320.02070.059*
H4A20.17560.34760.01970.059*
C5A0.2616 (13)0.1887 (10)0.0683 (6)0.064 (3)
H5A10.18490.17240.05210.077*0.68
H5A20.25230.18470.11710.077*0.68
H5A30.19430.19350.10120.077*0.32
H5A40.23250.15650.03630.077*0.32
C6A0.3899 (19)0.0961 (15)0.0651 (11)0.066 (4)0.68
H6A10.37060.02580.08520.079*0.68
H6A20.40590.10620.01600.079*0.68
C7A0.5121 (18)0.0950 (15)0.1022 (9)0.059 (3)0.68
H7A10.55650.02020.12760.070*0.68
H7A20.48820.13100.13690.070*0.68
C6E0.380 (4)0.111 (3)0.1092 (19)0.063 (7)0.32
H6E10.35940.04230.13360.075*0.32
H6E20.40820.13820.14430.075*0.32
C7E0.496 (4)0.092 (3)0.060 (2)0.063 (6)0.32
H7E10.53480.01500.07540.075*0.32
H7E20.45650.11270.01300.075*0.32
C8A0.6081 (13)0.1486 (10)0.0553 (7)0.066 (3)
H8A10.63660.10840.02330.079*0.68
H8A20.68460.14030.08500.079*0.68
H8A30.68030.11380.03380.079*0.32
H8A40.63930.14180.10220.079*0.32
C9A0.5614 (11)0.2692 (10)0.0110 (5)0.055 (2)
H9A10.63730.29720.00500.066*
H9A20.50890.27580.03030.066*
C10A0.4826 (9)0.3370 (8)0.0500 (4)0.0400 (19)
C11A0.1701 (12)0.4392 (11)0.1149 (6)0.068 (3)
H11A0.12040.40310.09480.102*
H11B0.16680.41470.16520.102*
H11C0.13370.51610.09640.102*
Se1B0.17468 (11)0.16520 (9)0.68091 (5)0.0477 (3)
N1B0.3405 (9)0.0958 (7)0.7154 (4)0.051 (2)
N2B0.4185 (8)0.1591 (7)0.6874 (4)0.0462 (18)
C3B0.3660 (10)0.2609 (8)0.6410 (4)0.043 (2)
C4B0.4498 (12)0.3365 (10)0.6062 (6)0.059 (3)
H4B10.52910.31820.63630.070*
H4B20.40320.40980.60220.070*
C5B0.4881 (13)0.3346 (13)0.5336 (7)0.078 (4)
H5B10.56130.36790.52130.093*
H5B20.51730.25980.53510.093*
C6B0.3785 (16)0.3924 (16)0.4771 (8)0.101 (5)
H6B10.33590.46080.48340.121*
H6B20.41620.40930.43180.121*
C7B0.2812 (15)0.3357 (16)0.4748 (7)0.093 (4)
H7B10.31700.25990.50170.112*
H7B20.26670.34010.42630.112*
C8B0.1477 (12)0.3714 (9)0.5016 (5)0.059 (3)
H8B10.09680.31960.50210.071*
H8B20.10200.44100.46860.071*
C9B0.1529 (10)0.3816 (8)0.5757 (5)0.047 (2)
H9B10.18880.44270.57360.057*
H9B20.06450.39600.59070.057*
C10B0.2340 (9)0.2818 (7)0.6286 (4)0.0366 (18)
C11B0.5560 (11)0.1129 (10)0.7106 (7)0.068 (3)
H11D0.60570.16430.68760.102*
H11E0.56710.09580.76070.102*
H11F0.58620.04800.69870.102*
Se1C1.06674 (11)0.40224 (9)0.75799 (5)0.0477 (3)
N1C0.9037 (9)0.4587 (7)0.7156 (4)0.051 (2)
N2C0.8211 (8)0.4127 (6)0.7556 (4)0.0405 (16)
C3C0.8670 (9)0.3333 (7)0.8188 (4)0.0398 (19)
C4C0.7769 (10)0.2783 (9)0.8665 (5)0.049 (2)
H4C10.68860.32430.85480.059*
H4C20.80200.27050.91460.059*
C5C0.7763 (11)0.1681 (10)0.8627 (6)0.062 (3)
H5C10.76850.17390.81350.074*
H5C20.69900.14790.88400.074*
C6C0.9014 (14)0.0730 (10)0.9001 (7)0.074 (4)
H6C10.91790.07540.94690.089*
H6C20.88050.00430.90570.089*
C7C1.0242 (13)0.0753 (10)0.8632 (7)0.068 (3)
H7C11.00120.11860.81400.082*
H7C21.06610.00200.86490.082*
C8C1.1226 (12)0.1195 (9)0.8919 (6)0.060 (3)
H8C11.19660.11840.86290.072*
H8C21.15430.06990.93890.072*
C9C1.0774 (9)0.2327 (8)0.8965 (5)0.044 (2)
H9C11.02580.22930.93700.052*
H9C21.15390.25720.90430.052*
C10C0.9986 (9)0.3137 (7)0.8333 (4)0.0361 (17)
C11C0.6841 (11)0.4514 (10)0.7276 (6)0.061 (3)
H11G0.63120.41310.76050.091*
H11H0.65490.52770.72040.091*
H11I0.67640.43910.68360.091*
Se1D0.66986 (10)0.14268 (8)0.25878 (5)0.0452 (2)
N1D0.8346 (8)0.0743 (6)0.2528 (4)0.0435 (17)
N2D0.9146 (8)0.1331 (7)0.2587 (4)0.0432 (17)
C3D0.8657 (9)0.2298 (7)0.2662 (4)0.0384 (18)
C4D0.9528 (11)0.3008 (9)0.2740 (6)0.052 (2)
H4D10.90760.37630.25190.062*
H4D21.03170.28640.24980.062*
C5D0.9904 (12)0.2806 (12)0.3512 (7)0.067 (3)
H5D11.02360.34100.35350.081*0.62
H5D21.06240.21630.36700.081*0.62
H5D31.07030.30300.35550.081*0.38
H5D41.00450.20420.37820.081*0.38
C6D0.883 (2)0.2653 (18)0.4049 (9)0.062 (5)0.62
H6D10.92100.25120.45180.075*0.62
H6D20.85090.20320.40520.075*0.62
C7D0.7664 (18)0.3690 (15)0.3851 (9)0.047 (4)0.62
H7D10.74560.38830.42710.057*0.62
H7D20.79430.42850.35150.057*0.62
C6H0.869 (4)0.352 (3)0.3793 (16)0.065 (9)0.38
H6H10.90110.36780.41890.079*0.38
H6H20.83400.42020.34220.079*0.38
C7H0.768 (3)0.297 (3)0.4005 (13)0.054 (7)0.38
H7H10.75070.29210.44880.065*0.38
H7H20.79620.22410.39870.065*0.38
C8D0.6420 (12)0.3557 (10)0.3536 (6)0.057 (3)
H8D10.56910.41400.35560.069*0.62
H8D20.62400.28790.38260.069*0.62
H8D30.61820.43020.35300.069*0.38
H8D40.57260.32210.37450.069*0.38
C9D0.6486 (10)0.3562 (8)0.2772 (5)0.047 (2)
H9D10.56040.36750.25770.056*
H9D20.68260.41700.24990.056*
C10D0.7316 (9)0.2549 (7)0.2693 (4)0.0355 (17)
C11D1.0563 (12)0.0861 (11)0.2558 (8)0.070 (3)
H11J1.10580.13530.26060.105*
H11K1.08380.01820.29340.105*
H11L1.07080.07430.21150.105*
I10.38141 (7)0.31708 (7)0.81714 (4)0.0639 (2)
I20.35417 (7)0.22279 (7)0.28803 (4)0.0632 (2)
I30.85843 (7)0.25666 (7)0.62885 (4)0.0628 (2)
I40.86700 (8)0.32453 (9)0.06828 (4)0.0809 (3)
C1L0.2649 (18)0.0221 (13)0.4924 (7)0.089 (5)
H1L0.29170.08440.45980.107*
Cl10.2328 (5)0.0580 (3)0.44457 (19)0.0949 (12)
Cl20.3942 (5)0.0512 (5)0.5587 (2)0.1172 (17)
Cl30.1264 (5)0.0702 (4)0.5302 (3)0.1084 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se1A0.0442 (6)0.0586 (6)0.0464 (5)0.0179 (5)0.0026 (4)0.0135 (4)
N1A0.049 (5)0.045 (4)0.053 (4)0.003 (4)0.002 (4)0.019 (3)
N2A0.034 (4)0.039 (4)0.049 (4)0.001 (3)0.001 (3)0.017 (3)
C3A0.036 (5)0.048 (5)0.035 (3)0.007 (4)0.001 (3)0.008 (3)
C4A0.031 (5)0.063 (5)0.056 (5)0.007 (4)0.001 (4)0.025 (4)
C5A0.051 (6)0.072 (6)0.072 (6)0.012 (4)0.004 (4)0.028 (5)
C6A0.054 (7)0.068 (8)0.088 (10)0.013 (6)0.000 (6)0.043 (7)
C7A0.048 (7)0.064 (8)0.065 (7)0.007 (6)0.000 (5)0.029 (6)
C6E0.054 (9)0.074 (12)0.059 (10)0.008 (7)0.008 (7)0.025 (8)
C7E0.056 (9)0.069 (11)0.064 (14)0.009 (8)0.009 (9)0.028 (10)
C8A0.047 (6)0.068 (6)0.084 (6)0.001 (5)0.010 (5)0.036 (5)
C9A0.042 (6)0.078 (6)0.050 (4)0.008 (5)0.001 (4)0.033 (4)
C10A0.034 (5)0.052 (5)0.034 (3)0.008 (4)0.004 (3)0.017 (3)
C11A0.045 (7)0.095 (9)0.072 (7)0.012 (6)0.006 (5)0.041 (7)
Se1B0.0339 (6)0.0460 (6)0.0570 (5)0.0073 (4)0.0049 (4)0.0105 (4)
N1B0.044 (5)0.048 (5)0.060 (4)0.015 (4)0.008 (4)0.014 (4)
N2B0.039 (5)0.047 (4)0.052 (4)0.004 (4)0.008 (3)0.019 (3)
C3B0.039 (5)0.048 (5)0.043 (4)0.012 (4)0.000 (3)0.016 (4)
C4B0.043 (6)0.058 (6)0.073 (5)0.018 (5)0.007 (4)0.016 (5)
C5B0.044 (6)0.106 (10)0.073 (5)0.016 (6)0.012 (4)0.016 (6)
C6B0.062 (7)0.153 (12)0.070 (6)0.010 (7)0.006 (5)0.026 (7)
C7B0.067 (7)0.158 (13)0.068 (6)0.011 (7)0.009 (5)0.066 (8)
C8B0.057 (6)0.056 (6)0.049 (4)0.002 (5)0.006 (4)0.009 (4)
C9B0.038 (5)0.043 (5)0.057 (4)0.005 (4)0.004 (4)0.014 (4)
C10B0.028 (4)0.037 (4)0.044 (4)0.002 (4)0.000 (3)0.016 (3)
C11B0.031 (6)0.072 (8)0.083 (7)0.002 (5)0.016 (5)0.010 (6)
Se1C0.0382 (6)0.0469 (6)0.0551 (5)0.0129 (5)0.0058 (4)0.0111 (4)
N1C0.055 (6)0.043 (4)0.050 (4)0.013 (4)0.006 (4)0.010 (3)
N2C0.033 (4)0.039 (4)0.047 (3)0.003 (3)0.001 (3)0.015 (3)
C3C0.030 (5)0.045 (5)0.044 (4)0.001 (4)0.001 (3)0.020 (4)
C4C0.028 (5)0.073 (7)0.049 (4)0.010 (5)0.005 (4)0.027 (5)
C5C0.040 (6)0.081 (8)0.073 (6)0.033 (6)0.011 (5)0.025 (6)
C6C0.068 (9)0.061 (7)0.088 (8)0.020 (7)0.020 (7)0.015 (6)
C7C0.054 (8)0.061 (7)0.095 (8)0.012 (6)0.014 (6)0.036 (6)
C8C0.049 (7)0.053 (6)0.059 (5)0.004 (5)0.004 (5)0.004 (5)
C9C0.028 (5)0.053 (5)0.047 (4)0.009 (4)0.001 (3)0.012 (4)
C10C0.031 (5)0.038 (4)0.043 (4)0.008 (4)0.004 (3)0.020 (3)
C11C0.035 (6)0.074 (7)0.061 (5)0.005 (5)0.006 (4)0.018 (5)
Se1D0.0334 (5)0.0458 (5)0.0609 (5)0.0070 (4)0.0001 (4)0.0252 (4)
N1D0.043 (5)0.032 (4)0.057 (4)0.003 (3)0.003 (3)0.021 (3)
N2D0.033 (4)0.050 (4)0.051 (4)0.011 (4)0.008 (3)0.022 (3)
C3D0.037 (5)0.037 (4)0.041 (4)0.006 (4)0.004 (3)0.016 (3)
C4D0.044 (6)0.049 (6)0.071 (6)0.021 (5)0.014 (5)0.026 (5)
C5D0.048 (7)0.100 (10)0.085 (7)0.036 (7)0.008 (6)0.060 (7)
C6D0.061 (13)0.068 (13)0.055 (9)0.006 (10)0.016 (8)0.023 (9)
C7D0.044 (11)0.042 (10)0.070 (9)0.014 (8)0.007 (7)0.034 (8)
C6H0.07 (2)0.08 (2)0.063 (16)0.022 (19)0.026 (16)0.039 (17)
C7H0.07 (2)0.039 (15)0.047 (12)0.003 (15)0.019 (13)0.022 (11)
C8D0.045 (6)0.063 (7)0.065 (6)0.003 (5)0.004 (5)0.034 (5)
C9D0.035 (5)0.047 (5)0.056 (5)0.008 (4)0.010 (4)0.025 (4)
C10D0.038 (5)0.032 (4)0.038 (3)0.006 (4)0.001 (3)0.015 (3)
C11D0.046 (7)0.066 (8)0.100 (9)0.002 (6)0.011 (6)0.041 (7)
I10.0370 (4)0.0961 (6)0.0605 (4)0.0179 (4)0.0050 (3)0.0273 (4)
I20.0343 (4)0.0734 (5)0.0798 (4)0.0090 (3)0.0032 (3)0.0255 (4)
I30.0353 (4)0.0766 (5)0.0836 (5)0.0098 (3)0.0041 (3)0.0386 (4)
I40.0440 (5)0.1349 (9)0.0612 (4)0.0310 (5)0.0053 (3)0.0222 (5)
C1L0.122 (15)0.086 (10)0.058 (6)0.036 (10)0.003 (7)0.013 (6)
Cl10.128 (4)0.088 (2)0.0743 (18)0.027 (2)0.020 (2)0.0343 (18)
Cl20.091 (3)0.159 (4)0.079 (2)0.044 (3)0.001 (2)0.002 (2)
Cl30.107 (4)0.124 (4)0.112 (3)0.021 (3)0.008 (3)0.067 (3)
Geometric parameters (Å, º) top
Se1A—N1A1.809 (10)N1C—N2C1.305 (11)
Se1A—C10A1.849 (9)N2C—C3C1.371 (11)
N1A—N2A1.302 (11)N2C—C11C1.463 (12)
N2A—C3A1.372 (12)C3C—C10C1.363 (12)
N2A—C11A1.459 (14)C3C—C4C1.490 (13)
C3A—C10A1.354 (13)C4C—C5C1.509 (16)
C3A—C4A1.489 (13)C4C—H4C10.9700
C4A—C5A1.496 (16)C4C—H4C20.9700
C4A—H4A10.9700C5C—C6C1.594 (18)
C4A—H4A20.9700C5C—H5C10.9700
C5A—C6E1.47 (4)C5C—H5C20.9700
C5A—C6A1.62 (2)C6C—C7C1.486 (18)
C5A—H5A10.9700C6C—H6C10.9700
C5A—H5A20.9700C6C—H6C20.9700
C5A—H5A30.9700C7C—C8C1.510 (17)
C5A—H5A40.9700C7C—H7C10.9700
C6A—C7A1.49 (2)C7C—H7C20.9700
C6A—H6A10.9700C8C—C9C1.517 (15)
C6A—H6A20.9700C8C—H8C10.9700
C7A—C8A1.52 (2)C8C—H8C20.9700
C7A—H7A10.9700C9C—C10C1.480 (11)
C7A—H7A20.9700C9C—H9C10.9700
C6E—C7E1.58 (5)C9C—H9C20.9700
C6E—H6E10.9700C11C—H11G0.9600
C6E—H6E20.9700C11C—H11H0.9600
C7E—C8A1.53 (4)C11C—H11I0.9600
C7E—H7E10.9700Se1D—N1D1.785 (8)
C7E—H7E20.9700Se1D—C10D1.846 (8)
C8A—C9A1.537 (16)N1D—N2D1.313 (11)
C8A—H8A10.9700N2D—C3D1.337 (12)
C8A—H8A20.9700N2D—C11D1.485 (14)
C8A—H8A30.9700C3D—C10D1.378 (13)
C8A—H8A40.9700C3D—C4D1.511 (13)
C9A—C10A1.492 (13)C4D—C5D1.527 (15)
C9A—H9A10.9700C4D—H4D10.9700
C9A—H9A20.9700C4D—H4D20.9700
C11A—H11A0.9600C5D—C6D1.56 (2)
C11A—H11B0.9600C5D—C6H1.62 (4)
C11A—H11C0.9600C5D—H5D10.9700
Se1B—N1B1.799 (9)C5D—H5D20.9700
Se1B—C10B1.826 (9)C5D—H5D30.9700
N1B—N2B1.312 (12)C5D—H5D40.9700
N2B—C3B1.370 (12)C6D—C7D1.57 (3)
N2B—C11B1.450 (12)C6D—H6D10.9700
C3B—C10B1.360 (13)C6D—H6D20.9700
C3B—C4B1.500 (14)C7D—C8D1.53 (2)
C4B—C5B1.518 (17)C7D—H7D10.9700
C4B—H4B10.9700C7D—H7D20.9700
C4B—H4B20.9700C6H—C7H1.42 (5)
C5B—C6B1.502 (19)C6H—H6H10.9700
C5B—H5B10.9700C6H—H6H20.9700
C5B—H5B20.9700C7H—C8D1.52 (3)
C6B—C7B1.42 (2)C7H—H7H10.9700
C6B—H6B10.9700C7H—H7H20.9700
C6B—H6B20.9700C8D—C9D1.535 (13)
C7B—C8B1.527 (18)C8D—H8D10.9700
C7B—H7B10.9700C8D—H8D20.9700
C7B—H7B20.9700C8D—H8D30.9700
C8B—C9B1.544 (14)C8D—H8D40.9700
C8B—H8B10.9700C9D—C10D1.491 (12)
C8B—H8B20.9700C9D—H9D10.9700
C9B—C10B1.489 (12)C9D—H9D20.9700
C9B—H9B10.9700C11D—H11J0.9600
C9B—H9B20.9700C11D—H11K0.9600
C11B—H11D0.9600C11D—H11L0.9600
C11B—H11E0.9600C1L—Cl31.726 (18)
C11B—H11F0.9600C1L—Cl11.744 (16)
Se1C—N1C1.802 (9)C1L—Cl21.777 (16)
Se1C—C10C1.854 (9)C1L—H1L0.9800
N1A—Se1A—C10A88.5 (4)N1C—N2C—C11C115.5 (8)
N2A—N1A—Se1A108.8 (7)C3C—N2C—C11C125.3 (8)
N1A—N2A—C3A120.4 (8)C10C—C3C—N2C113.8 (8)
N1A—N2A—C11A115.5 (9)C10C—C3C—C4C124.9 (8)
C3A—N2A—C11A124.0 (9)N2C—C3C—C4C121.3 (8)
C10A—C3A—N2A112.4 (8)C3C—C4C—C5C114.0 (9)
C10A—C3A—C4A125.9 (9)C3C—C4C—H4C1108.7
N2A—C3A—C4A121.7 (9)C5C—C4C—H4C1108.7
C3A—C4A—C5A115.0 (8)C3C—C4C—H4C2108.7
C3A—C4A—H4A1108.5C5C—C4C—H4C2108.7
C5A—C4A—H4A1108.5H4C1—C4C—H4C2107.6
C3A—C4A—H4A2108.5C4C—C5C—C6C115.7 (10)
C5A—C4A—H4A2108.5C4C—C5C—H5C1108.4
H4A1—C4A—H4A2107.5C6C—C5C—H5C1108.4
C6E—C5A—C4A121 (2)C4C—C5C—H5C2108.4
C4A—C5A—C6A115.1 (12)C6C—C5C—H5C2108.4
C4A—C5A—H5A1108.5H5C1—C5C—H5C2107.4
C6A—C5A—H5A1108.5C7C—C6C—C5C116.1 (11)
C4A—C5A—H5A2108.5C7C—C6C—H6C1108.3
C6A—C5A—H5A2108.5C5C—C6C—H6C1108.3
H5A1—C5A—H5A2107.5C7C—C6C—H6C2108.3
C6E—C5A—H5A3107.0C5C—C6C—H6C2108.3
C4A—C5A—H5A3107.0H6C1—C6C—H6C2107.4
C6E—C5A—H5A4107.0C6C—C7C—C8C115.8 (12)
C4A—C5A—H5A4107.0C6C—C7C—H7C1108.3
H5A3—C5A—H5A4106.8C8C—C7C—H7C1108.3
C7A—C6A—C5A115.4 (14)C6C—C7C—H7C2108.3
C7A—C6A—H6A1108.4C8C—C7C—H7C2108.3
C5A—C6A—H6A1108.4H7C1—C7C—H7C2107.4
C7A—C6A—H6A2108.4C7C—C8C—C9C117.8 (10)
C5A—C6A—H6A2108.4C7C—C8C—H8C1107.9
H6A1—C6A—H6A2107.5C9C—C8C—H8C1107.9
C6A—C7A—C8A115.4 (16)C7C—C8C—H8C2107.9
C6A—C7A—H7A1108.4C9C—C8C—H8C2107.9
C8A—C7A—H7A1108.4H8C1—C8C—H8C2107.2
C6A—C7A—H7A2108.4C10C—C9C—C8C114.4 (8)
C8A—C7A—H7A2108.4C10C—C9C—H9C1108.7
H7A1—C7A—H7A2107.5C8C—C9C—H9C1108.7
C5A—C6E—C7E112 (3)C10C—C9C—H9C2108.7
C5A—C6E—H6E1109.3C8C—C9C—H9C2108.7
C7E—C6E—H6E1109.3H9C1—C9C—H9C2107.6
C5A—C6E—H6E2109.3C3C—C10C—C9C126.8 (8)
C7E—C6E—H6E2109.3C3C—C10C—Se1C108.5 (6)
H6E1—C6E—H6E2107.9C9C—C10C—Se1C124.6 (7)
C8A—C7E—C6E121 (3)N2C—C11C—H11G109.5
C8A—C7E—H7E1107.0N2C—C11C—H11H109.5
C6E—C7E—H7E1107.0H11G—C11C—H11H109.5
C8A—C7E—H7E2107.0N2C—C11C—H11I109.5
C6E—C7E—H7E2107.0H11G—C11C—H11I109.5
H7E1—C7E—H7E2106.8H11H—C11C—H11I109.5
C7A—C8A—C9A118.2 (11)N1D—Se1D—C10D88.8 (4)
C7E—C8A—C9A110.3 (18)N2D—N1D—Se1D109.8 (6)
C7A—C8A—H8A1107.8N1D—N2D—C3D119.3 (8)
C9A—C8A—H8A1107.8N1D—N2D—C11D116.3 (9)
C7A—C8A—H8A2107.8C3D—N2D—C11D124.4 (9)
C9A—C8A—H8A2107.8N2D—C3D—C10D113.9 (8)
H8A1—C8A—H8A2107.1N2D—C3D—C4D121.8 (9)
C7E—C8A—H8A3109.6C10D—C3D—C4D124.2 (9)
C9A—C8A—H8A3109.6C3D—C4D—C5D111.7 (9)
C7E—C8A—H8A4109.6C3D—C4D—H4D1109.3
C9A—C8A—H8A4109.6C5D—C4D—H4D1109.3
H8A3—C8A—H8A4108.1C3D—C4D—H4D2109.3
C10A—C9A—C8A113.6 (9)C5D—C4D—H4D2109.3
C10A—C9A—H9A1108.8H4D1—C4D—H4D2107.9
C8A—C9A—H9A1108.8C4D—C5D—C6D118.3 (11)
C10A—C9A—H9A2108.8C4D—C5D—C6H106.4 (13)
C8A—C9A—H9A2108.8C4D—C5D—H5D1107.7
H9A1—C9A—H9A2107.7C6D—C5D—H5D1107.7
C3A—C10A—C9A124.9 (9)C4D—C5D—H5D2107.7
C3A—C10A—Se1A109.8 (7)C6D—C5D—H5D2107.7
C9A—C10A—Se1A125.3 (7)H5D1—C5D—H5D2107.1
N2A—C11A—H11A109.5C4D—C5D—H5D3110.5
N2A—C11A—H11B109.5C6H—C5D—H5D3110.5
H11A—C11A—H11B109.5C4D—C5D—H5D4110.5
N2A—C11A—H11C109.5C6H—C5D—H5D4110.5
H11A—C11A—H11C109.5H5D3—C5D—H5D4108.6
H11B—C11A—H11C109.5C5D—C6D—C7D110.8 (16)
N1B—Se1B—C10B89.0 (4)C5D—C6D—H6D1109.5
N2B—N1B—Se1B109.2 (6)C7D—C6D—H6D1109.5
N1B—N2B—C3B119.2 (9)C5D—C6D—H6D2109.5
N1B—N2B—C11B115.0 (9)C7D—C6D—H6D2109.5
C3B—N2B—C11B125.8 (9)H6D1—C6D—H6D2108.1
C10B—C3B—N2B112.8 (8)C8D—C7D—C6D114.3 (14)
C10B—C3B—C4B125.2 (9)C8D—C7D—H7D1108.7
N2B—C3B—C4B121.9 (9)C6D—C7D—H7D1108.7
C3B—C4B—C5B114.9 (11)C8D—C7D—H7D2108.7
C3B—C4B—H4B1108.6C6D—C7D—H7D2108.7
C5B—C4B—H4B1108.6H7D1—C7D—H7D2107.6
C3B—C4B—H4B2108.6C7H—C6H—C5D112 (3)
C5B—C4B—H4B2108.6C7H—C6H—H6H1109.2
H4B1—C4B—H4B2107.5C5D—C6H—H6H1109.2
C6B—C5B—C4B113.4 (12)C7H—C6H—H6H2109.2
C6B—C5B—H5B1108.9C5D—C6H—H6H2109.2
C4B—C5B—H5B1108.9H6H1—C6H—H6H2107.9
C6B—C5B—H5B2108.9C6H—C7H—C8D112 (3)
C4B—C5B—H5B2108.9C6H—C7H—H7H1109.3
H5B1—C5B—H5B2107.7C8D—C7H—H7H1109.3
C7B—C6B—C5B116.1 (16)C6H—C7H—H7H2109.3
C7B—C6B—H6B1108.3C8D—C7H—H7H2109.3
C5B—C6B—H6B1108.3H7H1—C7H—H7H2107.9
C7B—C6B—H6B2108.3C7H—C8D—C9D115.3 (12)
C5B—C6B—H6B2108.3C7D—C8D—C9D114.7 (11)
H6B1—C6B—H6B2107.4C7D—C8D—H8D1108.6
C6B—C7B—C8B118.6 (14)C9D—C8D—H8D1108.6
C6B—C7B—H7B1107.7C7D—C8D—H8D2108.6
C8B—C7B—H7B1107.7C9D—C8D—H8D2108.6
C6B—C7B—H7B2107.7H8D1—C8D—H8D2107.6
C8B—C7B—H7B2107.7C7H—C8D—H8D3108.5
H7B1—C7B—H7B2107.1C9D—C8D—H8D3108.5
C7B—C8B—C9B114.8 (10)C7H—C8D—H8D4108.5
C7B—C8B—H8B1108.6C9D—C8D—H8D4108.4
C9B—C8B—H8B1108.6H8D3—C8D—H8D4107.5
C7B—C8B—H8B2108.6C10D—C9D—C8D114.2 (8)
C9B—C8B—H8B2108.6C10D—C9D—H9D1108.7
H8B1—C8B—H8B2107.5C8D—C9D—H9D1108.7
C10B—C9B—C8B112.3 (8)C10D—C9D—H9D2108.7
C10B—C9B—H9B1109.1C8D—C9D—H9D2108.7
C8B—C9B—H9B1109.1H9D1—C9D—H9D2107.6
C10B—C9B—H9B2109.1C3D—C10D—C9D126.6 (8)
C8B—C9B—H9B2109.1C3D—C10D—Se1D108.1 (6)
H9B1—C9B—H9B2107.9C9D—C10D—Se1D125.2 (7)
C3B—C10B—C9B124.5 (9)N2D—C11D—H11J109.5
C3B—C10B—Se1B109.8 (6)N2D—C11D—H11K109.5
C9B—C10B—Se1B125.5 (7)H11J—C11D—H11K109.5
N2B—C11B—H11D109.5N2D—C11D—H11L109.5
N2B—C11B—H11E109.5H11J—C11D—H11L109.5
H11D—C11B—H11E109.5H11K—C11D—H11L109.5
N2B—C11B—H11F109.5Cl3—C1L—Cl1110.9 (10)
H11D—C11B—H11F109.5Cl3—C1L—Cl2109.7 (8)
H11E—C11B—H11F109.5Cl1—C1L—Cl2111.2 (9)
N1C—Se1C—C10C88.8 (4)Cl3—C1L—H1L108.3
N2C—N1C—Se1C109.7 (6)Cl1—C1L—H1L108.3
N1C—N2C—C3C119.2 (8)Cl2—C1L—H1L108.3
C10A—Se1A—N1A—N2A2.7 (6)C10C—Se1C—N1C—N2C0.3 (7)
Se1A—N1A—N2A—C3A4.3 (10)Se1C—N1C—N2C—C3C0.7 (10)
Se1A—N1A—N2A—C11A177.0 (7)Se1C—N1C—N2C—C11C179.7 (7)
N1A—N2A—C3A—C10A3.8 (11)N1C—N2C—C3C—C10C1.7 (12)
C11A—N2A—C3A—C10A177.6 (9)C11C—N2C—C3C—C10C178.7 (9)
N1A—N2A—C3A—C4A177.8 (8)N1C—N2C—C3C—C4C179.8 (9)
C11A—N2A—C3A—C4A0.9 (13)C11C—N2C—C3C—C4C0.6 (14)
C10A—C3A—C4A—C5A83.2 (12)C10C—C3C—C4C—C5C81.6 (12)
N2A—C3A—C4A—C5A95.0 (11)N2C—C3C—C4C—C5C100.4 (11)
C3A—C4A—C5A—C6E34 (2)C3C—C4C—C5C—C6C74.6 (12)
C3A—C4A—C5A—C6A75.0 (14)C4C—C5C—C6C—C7C73.4 (15)
C4A—C5A—C6A—C7A70.9 (19)C5C—C6C—C7C—C8C101.0 (14)
C5A—C6A—C7A—C8A100.3 (19)C6C—C7C—C8C—C9C56.3 (15)
C4A—C5A—C6E—C7E60 (4)C7C—C8C—C9C—C10C44.3 (14)
C5A—C6E—C7E—C8A101 (4)N2C—C3C—C10C—C9C179.3 (8)
C6A—C7A—C8A—C9A59.8 (19)C4C—C3C—C10C—C9C2.6 (15)
C6E—C7E—C8A—C9A74 (3)N2C—C3C—C10C—Se1C1.7 (10)
C7A—C8A—C9A—C10A42.3 (16)C4C—C3C—C10C—Se1C179.8 (8)
C7E—C8A—C9A—C10A77.8 (19)C8C—C9C—C10C—C3C84.7 (12)
N2A—C3A—C10A—C9A177.9 (8)C8C—C9C—C10C—Se1C92.5 (10)
C4A—C3A—C10A—C9A0.4 (14)N1C—Se1C—C10C—C3C1.1 (7)
N2A—C3A—C10A—Se1A1.2 (9)N1C—Se1C—C10C—C9C178.8 (8)
C4A—C3A—C10A—Se1A179.6 (7)C10D—Se1D—N1D—N2D0.3 (6)
C8A—C9A—C10A—C3A85.2 (12)Se1D—N1D—N2D—C3D1.5 (10)
C8A—C9A—C10A—Se1A93.8 (11)Se1D—N1D—N2D—C11D179.1 (8)
N1A—Se1A—C10A—C3A0.8 (6)N1D—N2D—C3D—C10D2.2 (11)
N1A—Se1A—C10A—C9A180.0 (8)C11D—N2D—C3D—C10D178.4 (9)
C10B—Se1B—N1B—N2B0.3 (7)N1D—N2D—C3D—C4D179.5 (8)
Se1B—N1B—N2B—C3B1.2 (11)C11D—N2D—C3D—C4D1.2 (14)
Se1B—N1B—N2B—C11B179.8 (8)N2D—C3D—C4D—C5D92.3 (12)
N1B—N2B—C3B—C10B1.7 (12)C10D—C3D—C4D—C5D84.7 (12)
C11B—N2B—C3B—C10B179.4 (10)C3D—C4D—C5D—C6D41.4 (17)
N1B—N2B—C3B—C4B178.8 (9)C3D—C4D—C5D—C6H82.7 (17)
C11B—N2B—C3B—C4B2.3 (15)C4D—C5D—C6D—C7D60.7 (19)
C10B—C3B—C4B—C5B81.8 (14)C5D—C6D—C7D—C8D106.2 (17)
N2B—C3B—C4B—C5B95.0 (12)C4D—C5D—C6H—C7H84 (2)
C3B—C4B—C5B—C6B75.4 (17)C5D—C6H—C7H—C8D115 (2)
C4B—C5B—C6B—C7B77.2 (19)C6H—C7H—C8D—C9D67 (3)
C5B—C6B—C7B—C8B105.5 (18)C6D—C7D—C8D—C9D74.5 (18)
C6B—C7B—C8B—C9B51.1 (18)C7H—C8D—C9D—C10D36 (2)
C7B—C8B—C9B—C10B52.1 (15)C7D—C8D—C9D—C10D73.9 (14)
N2B—C3B—C10B—C9B174.1 (8)N2D—C3D—C10D—C9D179.8 (8)
C4B—C3B—C10B—C9B2.9 (15)C4D—C3D—C10D—C9D3.1 (14)
N2B—C3B—C10B—Se1B1.3 (10)N2D—C3D—C10D—Se1D1.8 (9)
C4B—C3B—C10B—Se1B178.3 (8)C4D—C3D—C10D—Se1D178.9 (7)
C8B—C9B—C10B—C3B86.2 (12)C8D—C9D—C10D—C3D83.3 (12)
C8B—C9B—C10B—Se1B88.4 (10)C8D—C9D—C10D—Se1D99.0 (9)
N1B—Se1B—C10B—C3B0.6 (7)N1D—Se1D—C10D—C3D0.8 (6)
N1B—Se1B—C10B—C9B174.7 (8)N1D—Se1D—C10D—C9D178.8 (7)
 

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