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

Schollmeyer, D.; Detert, H.

doi:10.1107/S2414314617001675

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

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.

Keywords: crystal structure; selenium; heterocycles.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617001675/bt4038sup1.cif Contains datablocks I, New_Global_Publ_Block
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314617001675/bt4038Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617001675/bt4038Isup3.cml Supplementary material

CCDC reference: 815133

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.017 Å
Disorder in main residue
R factor = 0.067
wR factor = 0.197
Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT431_ALERT_2_A Short Inter HL..A  Contact I1     ..  Se1C    ..       3.33 Ang.

Author Response: Will be descriped in the text

PLAT431_ALERT_2_A Short Inter HL..A  Contact I2     ..  Se1D    ..       3.35 Ang.

Author Response: Will be descriped in the text

PLAT431_ALERT_2_A Short Inter HL..A  Contact I3     ..  Se1B    ..       3.32 Ang.

Author Response: Will be descriped in the text


Alert level B
PLAT431_ALERT_2_B Short Inter HL..A  Contact I4     ..  Se1A    ..       3.40 Ang.

Author Response: Will be descriped in the text


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C1L Check
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01677 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond   C6B    -   C7B    ..       1.42 Ang.
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check
PLAT971_ALERT_2_C Check Calcd Residual Density  0.90A From      I1       1.66 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H4A2      -0.33 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H7A1      -0.32 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H11E      -0.31 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H11F      -0.34 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H11H      -0.51 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H11I      -0.47 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H11K      -0.44 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         14 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.10 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          2 Report
PLAT300_ALERT_4_G Atom Site Occupancy of >C6A    is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C7A    is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C6E    is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C7E    is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H5A1   is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H5A2   is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H6A1   is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H6A2   is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H7A1   is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H7A2   is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H8A1   is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H8A2   is Constrained at       0.68 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H5A3   is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H5A4   is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H6E1   is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H6E2   is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H7E1   is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H7E2   is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H8A3   is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H8A4   is Constrained at       0.32 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C6D    is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C7D    is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C6H    is Constrained at       0.38 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C7H    is Constrained at       0.38 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H5D1   is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H5D2   is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H6D1   is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H6D2   is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H7D1   is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H7D2   is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H8D1   is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H8D2   is Constrained at       0.62 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H5D3   is Constrained at       0.38 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H5D4   is Constrained at       0.38 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H6H1   is Constrained at       0.38 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H6H2   is Constrained at       0.38 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H7H1   is Constrained at       0.38 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H7H2   is Constrained at       0.38 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H8D3   is Constrained at       0.38 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H8D4   is Constrained at       0.38 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..         17 % Note
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  2)..         17 % Note
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....       C11A Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....       C11D Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....       C11B Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....       C11C Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         64 Note
PLAT721_ALERT_1_G Bond    Calc     0.96000, Rep     0.97000 Dev...       0.01 Ang.
              C7E    -H7E1          1.555   1.555 ............     #   27 Check
PLAT721_ALERT_1_G Bond    Calc     0.96000, Rep     0.97000 Dev...       0.01 Ang.
              C7E    -H7E2          1.555   1.555 ............     #   28 Check
PLAT722_ALERT_1_G Angle   Calc      108.00, Rep      106.80 Dev...       1.20 Degree
              H7E1 -C7E  -H7E2      1.555   1.555   1.555 ....     #   50 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         75 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note

   3 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
  13 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  56 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  17 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
  47 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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⁻·CHCl₃	Z = 2
M_r = 1547.73	F(000) = 1476
Triclinic, P1	D_x = 1.969 Mg m⁻³
a = 10.5250 (9) Å	Cu Kα radiation, λ = 1.54178 Å
b = 13.4368 (9) Å	Cell parameters from 25 reflections
c = 20.112 (2) Å	θ = 24–38°
α = 71.141 (8)°	µ = 23.62 mm⁻¹
β = 89.472 (9)°	T = 295 K
γ = 76.460 (6)°	Plate, yellow
V = 2609.9 (4) Å³	0.56 × 0.32 × 0.12 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	7331 reflections with I > 2σ(I)
Radiation source: Rotating anode	R_int = 0.067
ω/2θ scan	θ_max = 74.0°, θ_min = 2.3°
Absorption correction: numerical (PLATON; Spek, 2009)	h = −13→0
T_min = 0.006, T_max = 0.202	k = −16→16
11193 measured reflections	l = −25→25
10589 independent reflections	3 standard reflections every 60 min

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.067	w = 1/[σ²(F_o²) + (0.1024P)² + 1.7825P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.197	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 1.84 e Å⁻³
10589 reflections	Δρ_min = −1.19 e Å⁻³
542 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
75 restraints	Extinction 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Se1A	0.54844 (11)	0.41276 (9)	0.09780 (5)	0.0497 (3)
N1A	0.3841 (9)	0.4588 (7)	0.1214 (4)	0.0498 (19)
N2A	0.3060 (8)	0.4144 (6)	0.0971 (4)	0.0413 (16)
C3A	0.3520 (9)	0.3509 (8)	0.0564 (4)	0.041 (2)
C4A	0.2640 (10)	0.3023 (9)	0.0257 (5)	0.049 (2)
H4A1	0.2911	0.3032	−0.0207	0.059*
H4A2	0.1756	0.3476	0.0197	0.059*
C5A	0.2616 (13)	0.1887 (10)	0.0683 (6)	0.064 (3)
H5A1	0.1849	0.1724	0.0521	0.077*	0.68
H5A2	0.2523	0.1847	0.1171	0.077*	0.68
H5A3	0.1943	0.1935	0.1012	0.077*	0.32
H5A4	0.2325	0.1565	0.0363	0.077*	0.32
C6A	0.3899 (19)	0.0961 (15)	0.0651 (11)	0.066 (4)	0.68
H6A1	0.3706	0.0258	0.0852	0.079*	0.68
H6A2	0.4059	0.1062	0.0160	0.079*	0.68
C7A	0.5121 (18)	0.0950 (15)	0.1022 (9)	0.059 (3)	0.68
H7A1	0.5565	0.0202	0.1276	0.070*	0.68
H7A2	0.4882	0.1310	0.1369	0.070*	0.68
C6E	0.380 (4)	0.111 (3)	0.1092 (19)	0.063 (7)	0.32
H6E1	0.3594	0.0423	0.1336	0.075*	0.32
H6E2	0.4082	0.1382	0.1443	0.075*	0.32
C7E	0.496 (4)	0.092 (3)	0.060 (2)	0.063 (6)	0.32
H7E1	0.5348	0.0150	0.0754	0.075*	0.32
H7E2	0.4565	0.1127	0.0130	0.075*	0.32
C8A	0.6081 (13)	0.1486 (10)	0.0553 (7)	0.066 (3)
H8A1	0.6366	0.1084	0.0233	0.079*	0.68
H8A2	0.6846	0.1403	0.0850	0.079*	0.68
H8A3	0.6803	0.1138	0.0338	0.079*	0.32
H8A4	0.6393	0.1418	0.1022	0.079*	0.32
C9A	0.5614 (11)	0.2692 (10)	0.0110 (5)	0.055 (2)
H9A1	0.6373	0.2972	−0.0050	0.066*
H9A2	0.5089	0.2758	−0.0303	0.066*
C10A	0.4826 (9)	0.3370 (8)	0.0500 (4)	0.0400 (19)
C11A	0.1701 (12)	0.4392 (11)	0.1149 (6)	0.068 (3)
H11A	0.1204	0.4031	0.0948	0.102*
H11B	0.1668	0.4147	0.1652	0.102*
H11C	0.1337	0.5161	0.0964	0.102*
Se1B	0.17468 (11)	0.16520 (9)	0.68091 (5)	0.0477 (3)
N1B	0.3405 (9)	0.0958 (7)	0.7154 (4)	0.051 (2)
N2B	0.4185 (8)	0.1591 (7)	0.6874 (4)	0.0462 (18)
C3B	0.3660 (10)	0.2609 (8)	0.6410 (4)	0.043 (2)
C4B	0.4498 (12)	0.3365 (10)	0.6062 (6)	0.059 (3)
H4B1	0.5291	0.3182	0.6363	0.070*
H4B2	0.4032	0.4098	0.6022	0.070*
C5B	0.4881 (13)	0.3346 (13)	0.5336 (7)	0.078 (4)
H5B1	0.5613	0.3679	0.5213	0.093*
H5B2	0.5173	0.2598	0.5351	0.093*
C6B	0.3785 (16)	0.3924 (16)	0.4771 (8)	0.101 (5)
H6B1	0.3359	0.4608	0.4834	0.121*
H6B2	0.4162	0.4093	0.4318	0.121*
C7B	0.2812 (15)	0.3357 (16)	0.4748 (7)	0.093 (4)
H7B1	0.3170	0.2599	0.5017	0.112*
H7B2	0.2667	0.3401	0.4263	0.112*
C8B	0.1477 (12)	0.3714 (9)	0.5016 (5)	0.059 (3)
H8B1	0.0968	0.3196	0.5021	0.071*
H8B2	0.1020	0.4410	0.4686	0.071*
C9B	0.1529 (10)	0.3816 (8)	0.5757 (5)	0.047 (2)
H9B1	0.1888	0.4427	0.5736	0.057*
H9B2	0.0645	0.3960	0.5907	0.057*
C10B	0.2340 (9)	0.2818 (7)	0.6286 (4)	0.0366 (18)
C11B	0.5560 (11)	0.1129 (10)	0.7106 (7)	0.068 (3)
H11D	0.6057	0.1643	0.6876	0.102*
H11E	0.5671	0.0958	0.7607	0.102*
H11F	0.5862	0.0480	0.6987	0.102*
Se1C	1.06674 (11)	0.40224 (9)	0.75799 (5)	0.0477 (3)
N1C	0.9037 (9)	0.4587 (7)	0.7156 (4)	0.051 (2)
N2C	0.8211 (8)	0.4127 (6)	0.7556 (4)	0.0405 (16)
C3C	0.8670 (9)	0.3333 (7)	0.8188 (4)	0.0398 (19)
C4C	0.7769 (10)	0.2783 (9)	0.8665 (5)	0.049 (2)
H4C1	0.6886	0.3243	0.8548	0.059*
H4C2	0.8020	0.2705	0.9146	0.059*
C5C	0.7763 (11)	0.1681 (10)	0.8627 (6)	0.062 (3)
H5C1	0.7685	0.1739	0.8135	0.074*
H5C2	0.6990	0.1479	0.8840	0.074*
C6C	0.9014 (14)	0.0730 (10)	0.9001 (7)	0.074 (4)
H6C1	0.9179	0.0754	0.9469	0.089*
H6C2	0.8805	0.0043	0.9057	0.089*
C7C	1.0242 (13)	0.0753 (10)	0.8632 (7)	0.068 (3)
H7C1	1.0012	0.1186	0.8140	0.082*
H7C2	1.0661	0.0020	0.8649	0.082*
C8C	1.1226 (12)	0.1195 (9)	0.8919 (6)	0.060 (3)
H8C1	1.1966	0.1184	0.8629	0.072*
H8C2	1.1543	0.0699	0.9389	0.072*
C9C	1.0774 (9)	0.2327 (8)	0.8965 (5)	0.044 (2)
H9C1	1.0258	0.2293	0.9370	0.052*
H9C2	1.1539	0.2572	0.9043	0.052*
C10C	0.9986 (9)	0.3137 (7)	0.8333 (4)	0.0361 (17)
C11C	0.6841 (11)	0.4514 (10)	0.7276 (6)	0.061 (3)
H11G	0.6312	0.4131	0.7605	0.091*
H11H	0.6549	0.5277	0.7204	0.091*
H11I	0.6764	0.4391	0.6836	0.091*
Se1D	0.66986 (10)	0.14268 (8)	0.25878 (5)	0.0452 (2)
N1D	0.8346 (8)	0.0743 (6)	0.2528 (4)	0.0435 (17)
N2D	0.9146 (8)	0.1331 (7)	0.2587 (4)	0.0432 (17)
C3D	0.8657 (9)	0.2298 (7)	0.2662 (4)	0.0384 (18)
C4D	0.9528 (11)	0.3008 (9)	0.2740 (6)	0.052 (2)
H4D1	0.9076	0.3763	0.2519	0.062*
H4D2	1.0317	0.2864	0.2498	0.062*
C5D	0.9904 (12)	0.2806 (12)	0.3512 (7)	0.067 (3)
H5D1	1.0236	0.3410	0.3535	0.081*	0.62
H5D2	1.0624	0.2163	0.3670	0.081*	0.62
H5D3	1.0703	0.3030	0.3555	0.081*	0.38
H5D4	1.0045	0.2042	0.3782	0.081*	0.38
C6D	0.883 (2)	0.2653 (18)	0.4049 (9)	0.062 (5)	0.62
H6D1	0.9210	0.2512	0.4518	0.075*	0.62
H6D2	0.8509	0.2032	0.4052	0.075*	0.62
C7D	0.7664 (18)	0.3690 (15)	0.3851 (9)	0.047 (4)	0.62
H7D1	0.7456	0.3883	0.4271	0.057*	0.62
H7D2	0.7943	0.4285	0.3515	0.057*	0.62
C6H	0.869 (4)	0.352 (3)	0.3793 (16)	0.065 (9)	0.38
H6H1	0.9011	0.3678	0.4189	0.079*	0.38
H6H2	0.8340	0.4202	0.3422	0.079*	0.38
C7H	0.768 (3)	0.297 (3)	0.4005 (13)	0.054 (7)	0.38
H7H1	0.7507	0.2921	0.4488	0.065*	0.38
H7H2	0.7962	0.2241	0.3987	0.065*	0.38
C8D	0.6420 (12)	0.3557 (10)	0.3536 (6)	0.057 (3)
H8D1	0.5691	0.4140	0.3556	0.069*	0.62
H8D2	0.6240	0.2879	0.3826	0.069*	0.62
H8D3	0.6182	0.4302	0.3530	0.069*	0.38
H8D4	0.5726	0.3221	0.3745	0.069*	0.38
C9D	0.6486 (10)	0.3562 (8)	0.2772 (5)	0.047 (2)
H9D1	0.5604	0.3675	0.2577	0.056*
H9D2	0.6826	0.4170	0.2499	0.056*
C10D	0.7316 (9)	0.2549 (7)	0.2693 (4)	0.0355 (17)
C11D	1.0563 (12)	0.0861 (11)	0.2558 (8)	0.070 (3)
H11J	1.1058	0.1353	0.2606	0.105*
H11K	1.0838	0.0182	0.2934	0.105*
H11L	1.0708	0.0743	0.2115	0.105*
I1	0.38141 (7)	0.31708 (7)	0.81714 (4)	0.0639 (2)
I2	0.35417 (7)	0.22279 (7)	0.28803 (4)	0.0632 (2)
I3	0.85843 (7)	0.25666 (7)	0.62885 (4)	0.0628 (2)
I4	0.86700 (8)	0.32453 (9)	0.06828 (4)	0.0809 (3)
C1L	0.2649 (18)	0.0221 (13)	0.4924 (7)	0.089 (5)
H1L	0.2917	0.0844	0.4598	0.107*
Cl1	0.2328 (5)	−0.0580 (3)	0.44457 (19)	0.0949 (12)
Cl2	0.3942 (5)	−0.0512 (5)	0.5587 (2)	0.1172 (17)
Cl3	0.1264 (5)	0.0702 (4)	0.5302 (3)	0.1084 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1A	0.0442 (6)	0.0586 (6)	0.0464 (5)	−0.0179 (5)	−0.0026 (4)	−0.0135 (4)
N1A	0.049 (5)	0.045 (4)	0.053 (4)	−0.003 (4)	−0.002 (4)	−0.019 (3)
N2A	0.034 (4)	0.039 (4)	0.049 (4)	−0.001 (3)	−0.001 (3)	−0.017 (3)
C3A	0.036 (5)	0.048 (5)	0.035 (3)	−0.007 (4)	0.001 (3)	−0.008 (3)
C4A	0.031 (5)	0.063 (5)	0.056 (5)	−0.007 (4)	−0.001 (4)	−0.025 (4)
C5A	0.051 (6)	0.072 (6)	0.072 (6)	−0.012 (4)	0.004 (4)	−0.028 (5)
C6A	0.054 (7)	0.068 (8)	0.088 (10)	−0.013 (6)	0.000 (6)	−0.043 (7)
C7A	0.048 (7)	0.064 (8)	0.065 (7)	−0.007 (6)	0.000 (5)	−0.029 (6)
C6E	0.054 (9)	0.074 (12)	0.059 (10)	−0.008 (7)	0.008 (7)	−0.025 (8)
C7E	0.056 (9)	0.069 (11)	0.064 (14)	−0.009 (8)	0.009 (9)	−0.028 (10)
C8A	0.047 (6)	0.068 (6)	0.084 (6)	−0.001 (5)	0.010 (5)	−0.036 (5)
C9A	0.042 (6)	0.078 (6)	0.050 (4)	−0.008 (5)	0.001 (4)	−0.033 (4)
C10A	0.034 (5)	0.052 (5)	0.034 (3)	−0.008 (4)	0.004 (3)	−0.017 (3)
C11A	0.045 (7)	0.095 (9)	0.072 (7)	−0.012 (6)	0.006 (5)	−0.041 (7)
Se1B	0.0339 (6)	0.0460 (6)	0.0570 (5)	−0.0073 (4)	0.0049 (4)	−0.0105 (4)
N1B	0.044 (5)	0.048 (5)	0.060 (4)	−0.015 (4)	0.008 (4)	−0.014 (4)
N2B	0.039 (5)	0.047 (4)	0.052 (4)	−0.004 (4)	−0.008 (3)	−0.019 (3)
C3B	0.039 (5)	0.048 (5)	0.043 (4)	−0.012 (4)	0.000 (3)	−0.016 (4)
C4B	0.043 (6)	0.058 (6)	0.073 (5)	−0.018 (5)	0.007 (4)	−0.016 (5)
C5B	0.044 (6)	0.106 (10)	0.073 (5)	−0.016 (6)	0.012 (4)	−0.016 (6)
C6B	0.062 (7)	0.153 (12)	0.070 (6)	−0.010 (7)	0.006 (5)	−0.026 (7)
C7B	0.067 (7)	0.158 (13)	0.068 (6)	−0.011 (7)	0.009 (5)	−0.066 (8)
C8B	0.057 (6)	0.056 (6)	0.049 (4)	0.002 (5)	−0.006 (4)	−0.009 (4)
C9B	0.038 (5)	0.043 (5)	0.057 (4)	−0.005 (4)	0.004 (4)	−0.014 (4)
C10B	0.028 (4)	0.037 (4)	0.044 (4)	−0.002 (4)	0.000 (3)	−0.016 (3)
C11B	0.031 (6)	0.072 (8)	0.083 (7)	−0.002 (5)	−0.016 (5)	−0.010 (6)
Se1C	0.0382 (6)	0.0469 (6)	0.0551 (5)	−0.0129 (5)	0.0058 (4)	−0.0111 (4)
N1C	0.055 (6)	0.043 (4)	0.050 (4)	−0.013 (4)	0.006 (4)	−0.010 (3)
N2C	0.033 (4)	0.039 (4)	0.047 (3)	−0.003 (3)	0.001 (3)	−0.015 (3)
C3C	0.030 (5)	0.045 (5)	0.044 (4)	0.001 (4)	−0.001 (3)	−0.020 (4)
C4C	0.028 (5)	0.073 (7)	0.049 (4)	−0.010 (5)	0.005 (4)	−0.027 (5)
C5C	0.040 (6)	0.081 (8)	0.073 (6)	−0.033 (6)	0.011 (5)	−0.025 (6)
C6C	0.068 (9)	0.061 (7)	0.088 (8)	−0.020 (7)	0.020 (7)	−0.015 (6)
C7C	0.054 (8)	0.061 (7)	0.095 (8)	−0.012 (6)	0.014 (6)	−0.036 (6)
C8C	0.049 (7)	0.053 (6)	0.059 (5)	0.004 (5)	−0.004 (5)	−0.004 (5)
C9C	0.028 (5)	0.053 (5)	0.047 (4)	−0.009 (4)	−0.001 (3)	−0.012 (4)
C10C	0.031 (5)	0.038 (4)	0.043 (4)	−0.008 (4)	0.004 (3)	−0.020 (3)
C11C	0.035 (6)	0.074 (7)	0.061 (5)	0.005 (5)	−0.006 (4)	−0.018 (5)
Se1D	0.0334 (5)	0.0458 (5)	0.0609 (5)	−0.0070 (4)	0.0001 (4)	−0.0252 (4)
N1D	0.043 (5)	0.032 (4)	0.057 (4)	−0.003 (3)	0.003 (3)	−0.021 (3)
N2D	0.033 (4)	0.050 (4)	0.051 (4)	−0.011 (4)	0.008 (3)	−0.022 (3)
C3D	0.037 (5)	0.037 (4)	0.041 (4)	−0.006 (4)	0.004 (3)	−0.016 (3)
C4D	0.044 (6)	0.049 (6)	0.071 (6)	−0.021 (5)	0.014 (5)	−0.026 (5)
C5D	0.048 (7)	0.100 (10)	0.085 (7)	−0.036 (7)	0.008 (6)	−0.060 (7)
C6D	0.061 (13)	0.068 (13)	0.055 (9)	−0.006 (10)	−0.016 (8)	−0.023 (9)
C7D	0.044 (11)	0.042 (10)	0.070 (9)	−0.014 (8)	0.007 (7)	−0.034 (8)
C6H	0.07 (2)	0.08 (2)	0.063 (16)	−0.022 (19)	−0.026 (16)	−0.039 (17)
C7H	0.07 (2)	0.039 (15)	0.047 (12)	0.003 (15)	0.019 (13)	−0.022 (11)
C8D	0.045 (6)	0.063 (7)	0.065 (6)	0.003 (5)	0.004 (5)	−0.034 (5)
C9D	0.035 (5)	0.047 (5)	0.056 (5)	0.008 (4)	−0.010 (4)	−0.025 (4)
C10D	0.038 (5)	0.032 (4)	0.038 (3)	−0.006 (4)	0.001 (3)	−0.015 (3)
C11D	0.046 (7)	0.066 (8)	0.100 (9)	0.002 (6)	0.011 (6)	−0.041 (7)
I1	0.0370 (4)	0.0961 (6)	0.0605 (4)	−0.0179 (4)	0.0050 (3)	−0.0273 (4)
I2	0.0343 (4)	0.0734 (5)	0.0798 (4)	−0.0090 (3)	0.0032 (3)	−0.0255 (4)
I3	0.0353 (4)	0.0766 (5)	0.0836 (5)	−0.0098 (3)	0.0041 (3)	−0.0386 (4)
I4	0.0440 (5)	0.1349 (9)	0.0612 (4)	−0.0310 (5)	0.0053 (3)	−0.0222 (5)
C1L	0.122 (15)	0.086 (10)	0.058 (6)	−0.036 (10)	0.003 (7)	−0.013 (6)
Cl1	0.128 (4)	0.088 (2)	0.0743 (18)	−0.027 (2)	0.020 (2)	−0.0343 (18)
Cl2	0.091 (3)	0.159 (4)	0.079 (2)	−0.044 (3)	−0.001 (2)	0.002 (2)
Cl3	0.107 (4)	0.124 (4)	0.112 (3)	−0.021 (3)	0.008 (3)	−0.067 (3)

Geometric parameters (Å, º) top

Se1A—N1A	1.809 (10)	N1C—N2C	1.305 (11)
Se1A—C10A	1.849 (9)	N2C—C3C	1.371 (11)
N1A—N2A	1.302 (11)	N2C—C11C	1.463 (12)
N2A—C3A	1.372 (12)	C3C—C10C	1.363 (12)
N2A—C11A	1.459 (14)	C3C—C4C	1.490 (13)
C3A—C10A	1.354 (13)	C4C—C5C	1.509 (16)
C3A—C4A	1.489 (13)	C4C—H4C1	0.9700
C4A—C5A	1.496 (16)	C4C—H4C2	0.9700
C4A—H4A1	0.9700	C5C—C6C	1.594 (18)
C4A—H4A2	0.9700	C5C—H5C1	0.9700
C5A—C6E	1.47 (4)	C5C—H5C2	0.9700
C5A—C6A	1.62 (2)	C6C—C7C	1.486 (18)
C5A—H5A1	0.9700	C6C—H6C1	0.9700
C5A—H5A2	0.9700	C6C—H6C2	0.9700
C5A—H5A3	0.9700	C7C—C8C	1.510 (17)
C5A—H5A4	0.9700	C7C—H7C1	0.9700
C6A—C7A	1.49 (2)	C7C—H7C2	0.9700
C6A—H6A1	0.9700	C8C—C9C	1.517 (15)
C6A—H6A2	0.9700	C8C—H8C1	0.9700
C7A—C8A	1.52 (2)	C8C—H8C2	0.9700
C7A—H7A1	0.9700	C9C—C10C	1.480 (11)
C7A—H7A2	0.9700	C9C—H9C1	0.9700
C6E—C7E	1.58 (5)	C9C—H9C2	0.9700
C6E—H6E1	0.9700	C11C—H11G	0.9600
C6E—H6E2	0.9700	C11C—H11H	0.9600
C7E—C8A	1.53 (4)	C11C—H11I	0.9600
C7E—H7E1	0.9700	Se1D—N1D	1.785 (8)
C7E—H7E2	0.9700	Se1D—C10D	1.846 (8)
C8A—C9A	1.537 (16)	N1D—N2D	1.313 (11)
C8A—H8A1	0.9700	N2D—C3D	1.337 (12)
C8A—H8A2	0.9700	N2D—C11D	1.485 (14)
C8A—H8A3	0.9700	C3D—C10D	1.378 (13)
C8A—H8A4	0.9700	C3D—C4D	1.511 (13)
C9A—C10A	1.492 (13)	C4D—C5D	1.527 (15)
C9A—H9A1	0.9700	C4D—H4D1	0.9700
C9A—H9A2	0.9700	C4D—H4D2	0.9700
C11A—H11A	0.9600	C5D—C6D	1.56 (2)
C11A—H11B	0.9600	C5D—C6H	1.62 (4)
C11A—H11C	0.9600	C5D—H5D1	0.9700
Se1B—N1B	1.799 (9)	C5D—H5D2	0.9700
Se1B—C10B	1.826 (9)	C5D—H5D3	0.9700
N1B—N2B	1.312 (12)	C5D—H5D4	0.9700
N2B—C3B	1.370 (12)	C6D—C7D	1.57 (3)
N2B—C11B	1.450 (12)	C6D—H6D1	0.9700
C3B—C10B	1.360 (13)	C6D—H6D2	0.9700
C3B—C4B	1.500 (14)	C7D—C8D	1.53 (2)
C4B—C5B	1.518 (17)	C7D—H7D1	0.9700
C4B—H4B1	0.9700	C7D—H7D2	0.9700
C4B—H4B2	0.9700	C6H—C7H	1.42 (5)
C5B—C6B	1.502 (19)	C6H—H6H1	0.9700
C5B—H5B1	0.9700	C6H—H6H2	0.9700
C5B—H5B2	0.9700	C7H—C8D	1.52 (3)
C6B—C7B	1.42 (2)	C7H—H7H1	0.9700
C6B—H6B1	0.9700	C7H—H7H2	0.9700
C6B—H6B2	0.9700	C8D—C9D	1.535 (13)
C7B—C8B	1.527 (18)	C8D—H8D1	0.9700
C7B—H7B1	0.9700	C8D—H8D2	0.9700
C7B—H7B2	0.9700	C8D—H8D3	0.9700
C8B—C9B	1.544 (14)	C8D—H8D4	0.9700
C8B—H8B1	0.9700	C9D—C10D	1.491 (12)
C8B—H8B2	0.9700	C9D—H9D1	0.9700
C9B—C10B	1.489 (12)	C9D—H9D2	0.9700
C9B—H9B1	0.9700	C11D—H11J	0.9600
C9B—H9B2	0.9700	C11D—H11K	0.9600
C11B—H11D	0.9600	C11D—H11L	0.9600
C11B—H11E	0.9600	C1L—Cl3	1.726 (18)
C11B—H11F	0.9600	C1L—Cl1	1.744 (16)
Se1C—N1C	1.802 (9)	C1L—Cl2	1.777 (16)
Se1C—C10C	1.854 (9)	C1L—H1L	0.9800

N1A—Se1A—C10A	88.5 (4)	N1C—N2C—C11C	115.5 (8)
N2A—N1A—Se1A	108.8 (7)	C3C—N2C—C11C	125.3 (8)
N1A—N2A—C3A	120.4 (8)	C10C—C3C—N2C	113.8 (8)
N1A—N2A—C11A	115.5 (9)	C10C—C3C—C4C	124.9 (8)
C3A—N2A—C11A	124.0 (9)	N2C—C3C—C4C	121.3 (8)
C10A—C3A—N2A	112.4 (8)	C3C—C4C—C5C	114.0 (9)
C10A—C3A—C4A	125.9 (9)	C3C—C4C—H4C1	108.7
N2A—C3A—C4A	121.7 (9)	C5C—C4C—H4C1	108.7
C3A—C4A—C5A	115.0 (8)	C3C—C4C—H4C2	108.7
C3A—C4A—H4A1	108.5	C5C—C4C—H4C2	108.7
C5A—C4A—H4A1	108.5	H4C1—C4C—H4C2	107.6
C3A—C4A—H4A2	108.5	C4C—C5C—C6C	115.7 (10)
C5A—C4A—H4A2	108.5	C4C—C5C—H5C1	108.4
H4A1—C4A—H4A2	107.5	C6C—C5C—H5C1	108.4
C6E—C5A—C4A	121 (2)	C4C—C5C—H5C2	108.4
C4A—C5A—C6A	115.1 (12)	C6C—C5C—H5C2	108.4
C4A—C5A—H5A1	108.5	H5C1—C5C—H5C2	107.4
C6A—C5A—H5A1	108.5	C7C—C6C—C5C	116.1 (11)
C4A—C5A—H5A2	108.5	C7C—C6C—H6C1	108.3
C6A—C5A—H5A2	108.5	C5C—C6C—H6C1	108.3
H5A1—C5A—H5A2	107.5	C7C—C6C—H6C2	108.3
C6E—C5A—H5A3	107.0	C5C—C6C—H6C2	108.3
C4A—C5A—H5A3	107.0	H6C1—C6C—H6C2	107.4
C6E—C5A—H5A4	107.0	C6C—C7C—C8C	115.8 (12)
C4A—C5A—H5A4	107.0	C6C—C7C—H7C1	108.3
H5A3—C5A—H5A4	106.8	C8C—C7C—H7C1	108.3
C7A—C6A—C5A	115.4 (14)	C6C—C7C—H7C2	108.3
C7A—C6A—H6A1	108.4	C8C—C7C—H7C2	108.3
C5A—C6A—H6A1	108.4	H7C1—C7C—H7C2	107.4
C7A—C6A—H6A2	108.4	C7C—C8C—C9C	117.8 (10)
C5A—C6A—H6A2	108.4	C7C—C8C—H8C1	107.9
H6A1—C6A—H6A2	107.5	C9C—C8C—H8C1	107.9
C6A—C7A—C8A	115.4 (16)	C7C—C8C—H8C2	107.9
C6A—C7A—H7A1	108.4	C9C—C8C—H8C2	107.9
C8A—C7A—H7A1	108.4	H8C1—C8C—H8C2	107.2
C6A—C7A—H7A2	108.4	C10C—C9C—C8C	114.4 (8)
C8A—C7A—H7A2	108.4	C10C—C9C—H9C1	108.7
H7A1—C7A—H7A2	107.5	C8C—C9C—H9C1	108.7
C5A—C6E—C7E	112 (3)	C10C—C9C—H9C2	108.7
C5A—C6E—H6E1	109.3	C8C—C9C—H9C2	108.7
C7E—C6E—H6E1	109.3	H9C1—C9C—H9C2	107.6
C5A—C6E—H6E2	109.3	C3C—C10C—C9C	126.8 (8)
C7E—C6E—H6E2	109.3	C3C—C10C—Se1C	108.5 (6)
H6E1—C6E—H6E2	107.9	C9C—C10C—Se1C	124.6 (7)
C8A—C7E—C6E	121 (3)	N2C—C11C—H11G	109.5
C8A—C7E—H7E1	107.0	N2C—C11C—H11H	109.5
C6E—C7E—H7E1	107.0	H11G—C11C—H11H	109.5
C8A—C7E—H7E2	107.0	N2C—C11C—H11I	109.5
C6E—C7E—H7E2	107.0	H11G—C11C—H11I	109.5
H7E1—C7E—H7E2	106.8	H11H—C11C—H11I	109.5
C7A—C8A—C9A	118.2 (11)	N1D—Se1D—C10D	88.8 (4)
C7E—C8A—C9A	110.3 (18)	N2D—N1D—Se1D	109.8 (6)
C7A—C8A—H8A1	107.8	N1D—N2D—C3D	119.3 (8)
C9A—C8A—H8A1	107.8	N1D—N2D—C11D	116.3 (9)
C7A—C8A—H8A2	107.8	C3D—N2D—C11D	124.4 (9)
C9A—C8A—H8A2	107.8	N2D—C3D—C10D	113.9 (8)
H8A1—C8A—H8A2	107.1	N2D—C3D—C4D	121.8 (9)
C7E—C8A—H8A3	109.6	C10D—C3D—C4D	124.2 (9)
C9A—C8A—H8A3	109.6	C3D—C4D—C5D	111.7 (9)
C7E—C8A—H8A4	109.6	C3D—C4D—H4D1	109.3
C9A—C8A—H8A4	109.6	C5D—C4D—H4D1	109.3
H8A3—C8A—H8A4	108.1	C3D—C4D—H4D2	109.3
C10A—C9A—C8A	113.6 (9)	C5D—C4D—H4D2	109.3
C10A—C9A—H9A1	108.8	H4D1—C4D—H4D2	107.9
C8A—C9A—H9A1	108.8	C4D—C5D—C6D	118.3 (11)
C10A—C9A—H9A2	108.8	C4D—C5D—C6H	106.4 (13)
C8A—C9A—H9A2	108.8	C4D—C5D—H5D1	107.7
H9A1—C9A—H9A2	107.7	C6D—C5D—H5D1	107.7
C3A—C10A—C9A	124.9 (9)	C4D—C5D—H5D2	107.7
C3A—C10A—Se1A	109.8 (7)	C6D—C5D—H5D2	107.7
C9A—C10A—Se1A	125.3 (7)	H5D1—C5D—H5D2	107.1
N2A—C11A—H11A	109.5	C4D—C5D—H5D3	110.5
N2A—C11A—H11B	109.5	C6H—C5D—H5D3	110.5
H11A—C11A—H11B	109.5	C4D—C5D—H5D4	110.5
N2A—C11A—H11C	109.5	C6H—C5D—H5D4	110.5
H11A—C11A—H11C	109.5	H5D3—C5D—H5D4	108.6
H11B—C11A—H11C	109.5	C5D—C6D—C7D	110.8 (16)
N1B—Se1B—C10B	89.0 (4)	C5D—C6D—H6D1	109.5
N2B—N1B—Se1B	109.2 (6)	C7D—C6D—H6D1	109.5
N1B—N2B—C3B	119.2 (9)	C5D—C6D—H6D2	109.5
N1B—N2B—C11B	115.0 (9)	C7D—C6D—H6D2	109.5
C3B—N2B—C11B	125.8 (9)	H6D1—C6D—H6D2	108.1
C10B—C3B—N2B	112.8 (8)	C8D—C7D—C6D	114.3 (14)
C10B—C3B—C4B	125.2 (9)	C8D—C7D—H7D1	108.7
N2B—C3B—C4B	121.9 (9)	C6D—C7D—H7D1	108.7
C3B—C4B—C5B	114.9 (11)	C8D—C7D—H7D2	108.7
C3B—C4B—H4B1	108.6	C6D—C7D—H7D2	108.7
C5B—C4B—H4B1	108.6	H7D1—C7D—H7D2	107.6
C3B—C4B—H4B2	108.6	C7H—C6H—C5D	112 (3)
C5B—C4B—H4B2	108.6	C7H—C6H—H6H1	109.2
H4B1—C4B—H4B2	107.5	C5D—C6H—H6H1	109.2
C6B—C5B—C4B	113.4 (12)	C7H—C6H—H6H2	109.2
C6B—C5B—H5B1	108.9	C5D—C6H—H6H2	109.2
C4B—C5B—H5B1	108.9	H6H1—C6H—H6H2	107.9
C6B—C5B—H5B2	108.9	C6H—C7H—C8D	112 (3)
C4B—C5B—H5B2	108.9	C6H—C7H—H7H1	109.3
H5B1—C5B—H5B2	107.7	C8D—C7H—H7H1	109.3
C7B—C6B—C5B	116.1 (16)	C6H—C7H—H7H2	109.3
C7B—C6B—H6B1	108.3	C8D—C7H—H7H2	109.3
C5B—C6B—H6B1	108.3	H7H1—C7H—H7H2	107.9
C7B—C6B—H6B2	108.3	C7H—C8D—C9D	115.3 (12)
C5B—C6B—H6B2	108.3	C7D—C8D—C9D	114.7 (11)
H6B1—C6B—H6B2	107.4	C7D—C8D—H8D1	108.6
C6B—C7B—C8B	118.6 (14)	C9D—C8D—H8D1	108.6
C6B—C7B—H7B1	107.7	C7D—C8D—H8D2	108.6
C8B—C7B—H7B1	107.7	C9D—C8D—H8D2	108.6
C6B—C7B—H7B2	107.7	H8D1—C8D—H8D2	107.6
C8B—C7B—H7B2	107.7	C7H—C8D—H8D3	108.5
H7B1—C7B—H7B2	107.1	C9D—C8D—H8D3	108.5
C7B—C8B—C9B	114.8 (10)	C7H—C8D—H8D4	108.5
C7B—C8B—H8B1	108.6	C9D—C8D—H8D4	108.4
C9B—C8B—H8B1	108.6	H8D3—C8D—H8D4	107.5
C7B—C8B—H8B2	108.6	C10D—C9D—C8D	114.2 (8)
C9B—C8B—H8B2	108.6	C10D—C9D—H9D1	108.7
H8B1—C8B—H8B2	107.5	C8D—C9D—H9D1	108.7
C10B—C9B—C8B	112.3 (8)	C10D—C9D—H9D2	108.7
C10B—C9B—H9B1	109.1	C8D—C9D—H9D2	108.7
C8B—C9B—H9B1	109.1	H9D1—C9D—H9D2	107.6
C10B—C9B—H9B2	109.1	C3D—C10D—C9D	126.6 (8)
C8B—C9B—H9B2	109.1	C3D—C10D—Se1D	108.1 (6)
H9B1—C9B—H9B2	107.9	C9D—C10D—Se1D	125.2 (7)
C3B—C10B—C9B	124.5 (9)	N2D—C11D—H11J	109.5
C3B—C10B—Se1B	109.8 (6)	N2D—C11D—H11K	109.5
C9B—C10B—Se1B	125.5 (7)	H11J—C11D—H11K	109.5
N2B—C11B—H11D	109.5	N2D—C11D—H11L	109.5
N2B—C11B—H11E	109.5	H11J—C11D—H11L	109.5
H11D—C11B—H11E	109.5	H11K—C11D—H11L	109.5
N2B—C11B—H11F	109.5	Cl3—C1L—Cl1	110.9 (10)
H11D—C11B—H11F	109.5	Cl3—C1L—Cl2	109.7 (8)
H11E—C11B—H11F	109.5	Cl1—C1L—Cl2	111.2 (9)
N1C—Se1C—C10C	88.8 (4)	Cl3—C1L—H1L	108.3
N2C—N1C—Se1C	109.7 (6)	Cl1—C1L—H1L	108.3
N1C—N2C—C3C	119.2 (8)	Cl2—C1L—H1L	108.3

C10A—Se1A—N1A—N2A	2.7 (6)	C10C—Se1C—N1C—N2C	−0.3 (7)
Se1A—N1A—N2A—C3A	−4.3 (10)	Se1C—N1C—N2C—C3C	−0.7 (10)
Se1A—N1A—N2A—C11A	177.0 (7)	Se1C—N1C—N2C—C11C	179.7 (7)
N1A—N2A—C3A—C10A	3.8 (11)	N1C—N2C—C3C—C10C	1.7 (12)
C11A—N2A—C3A—C10A	−177.6 (9)	C11C—N2C—C3C—C10C	−178.7 (9)
N1A—N2A—C3A—C4A	−177.8 (8)	N1C—N2C—C3C—C4C	179.8 (9)
C11A—N2A—C3A—C4A	0.9 (13)	C11C—N2C—C3C—C4C	−0.6 (14)
C10A—C3A—C4A—C5A	83.2 (12)	C10C—C3C—C4C—C5C	−81.6 (12)
N2A—C3A—C4A—C5A	−95.0 (11)	N2C—C3C—C4C—C5C	100.4 (11)
C3A—C4A—C5A—C6E	−34 (2)	C3C—C4C—C5C—C6C	74.6 (12)
C3A—C4A—C5A—C6A	−75.0 (14)	C4C—C5C—C6C—C7C	−73.4 (15)
C4A—C5A—C6A—C7A	70.9 (19)	C5C—C6C—C7C—C8C	101.0 (14)
C5A—C6A—C7A—C8A	−100.3 (19)	C6C—C7C—C8C—C9C	−56.3 (15)
C4A—C5A—C6E—C7E	−60 (4)	C7C—C8C—C9C—C10C	−44.3 (14)
C5A—C6E—C7E—C8A	101 (4)	N2C—C3C—C10C—C9C	−179.3 (8)
C6A—C7A—C8A—C9A	59.8 (19)	C4C—C3C—C10C—C9C	2.6 (15)
C6E—C7E—C8A—C9A	−74 (3)	N2C—C3C—C10C—Se1C	−1.7 (10)
C7A—C8A—C9A—C10A	42.3 (16)	C4C—C3C—C10C—Se1C	−179.8 (8)
C7E—C8A—C9A—C10A	77.8 (19)	C8C—C9C—C10C—C3C	84.7 (12)
N2A—C3A—C10A—C9A	177.9 (8)	C8C—C9C—C10C—Se1C	−92.5 (10)
C4A—C3A—C10A—C9A	−0.4 (14)	N1C—Se1C—C10C—C3C	1.1 (7)
N2A—C3A—C10A—Se1A	−1.2 (9)	N1C—Se1C—C10C—C9C	178.8 (8)
C4A—C3A—C10A—Se1A	−179.6 (7)	C10D—Se1D—N1D—N2D	0.3 (6)
C8A—C9A—C10A—C3A	−85.2 (12)	Se1D—N1D—N2D—C3D	−1.5 (10)
C8A—C9A—C10A—Se1A	93.8 (11)	Se1D—N1D—N2D—C11D	179.1 (8)
N1A—Se1A—C10A—C3A	−0.8 (6)	N1D—N2D—C3D—C10D	2.2 (11)
N1A—Se1A—C10A—C9A	−180.0 (8)	C11D—N2D—C3D—C10D	−178.4 (9)
C10B—Se1B—N1B—N2B	−0.3 (7)	N1D—N2D—C3D—C4D	179.5 (8)
Se1B—N1B—N2B—C3B	1.2 (11)	C11D—N2D—C3D—C4D	−1.2 (14)
Se1B—N1B—N2B—C11B	−179.8 (8)	N2D—C3D—C4D—C5D	−92.3 (12)
N1B—N2B—C3B—C10B	−1.7 (12)	C10D—C3D—C4D—C5D	84.7 (12)
C11B—N2B—C3B—C10B	179.4 (10)	C3D—C4D—C5D—C6D	−41.4 (17)
N1B—N2B—C3B—C4B	−178.8 (9)	C3D—C4D—C5D—C6H	−82.7 (17)
C11B—N2B—C3B—C4B	2.3 (15)	C4D—C5D—C6D—C7D	−60.7 (19)
C10B—C3B—C4B—C5B	−81.8 (14)	C5D—C6D—C7D—C8D	106.2 (17)
N2B—C3B—C4B—C5B	95.0 (12)	C4D—C5D—C6H—C7H	84 (2)
C3B—C4B—C5B—C6B	75.4 (17)	C5D—C6H—C7H—C8D	−115 (2)
C4B—C5B—C6B—C7B	−77.2 (19)	C6H—C7H—C8D—C9D	67 (3)
C5B—C6B—C7B—C8B	105.5 (18)	C6D—C7D—C8D—C9D	−74.5 (18)
C6B—C7B—C8B—C9B	−51.1 (18)	C7H—C8D—C9D—C10D	36 (2)
C7B—C8B—C9B—C10B	−52.1 (15)	C7D—C8D—C9D—C10D	73.9 (14)
N2B—C3B—C10B—C9B	−174.1 (8)	N2D—C3D—C10D—C9D	−179.8 (8)
C4B—C3B—C10B—C9B	2.9 (15)	C4D—C3D—C10D—C9D	3.1 (14)
N2B—C3B—C10B—Se1B	1.3 (10)	N2D—C3D—C10D—Se1D	−1.8 (9)
C4B—C3B—C10B—Se1B	178.3 (8)	C4D—C3D—C10D—Se1D	−178.9 (7)
C8B—C9B—C10B—C3B	86.2 (12)	C8D—C9D—C10D—C3D	−83.3 (12)
C8B—C9B—C10B—Se1B	−88.4 (10)	C8D—C9D—C10D—Se1D	99.0 (9)
N1B—Se1B—C10B—C3B	−0.6 (7)	N1D—Se1D—C10D—C3D	0.8 (6)
N1B—Se1B—C10B—C9B	174.7 (8)	N1D—Se1D—C10D—C9D	178.8 (7)

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

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