3-Methyl-4,5,6,7,8,9-hexa­hydro­cyclo­octa­[d][1,2,3]selena­diazol]-3-ium iodide triiodide (3/2/1)

The title compound, 3C₉H₁₅N₂Se⁺·I₃⁻·2I⁻, was prepared by methyl­ation of the selena­diazole with methyl iodide. The asymmetric unit is composed of three independent selena­diazo­lium ions arranged in layers and connected via I₃⁻·(I⁻)₂ anion layers. The distances between the iodine and selenium atoms are significantly shorter than the nitro­gen-to-iodine distances.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.057
• wR factor = 0.149
• Data-to-parameter ratio = 25.2

checkCIF/PLATON results

No syntax errors found



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

Author Response: Will be descriped in the text

PLAT431_ALERT_2_A Short Inter HL..A  Contact I6     ..  Se1C    ..       3.31 Ang.

Author Response: Will be descriped in the text

PLAT431_ALERT_2_A Short Inter HL..A  Contact I6     ..  Se1A    ..       3.35 Ang.

Author Response: Will be descriped in the text

Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check
PLAT971_ALERT_2_B Check Calcd Residual Density  0.80A From    Se1A       3.35 eA-3
PLAT971_ALERT_2_B Check Calcd Residual Density  0.83A From    Se1C       3.20 eA-3
PLAT972_ALERT_2_B Check Calcd Residual Density  0.35A From      I6      -2.61 eA-3

Alert level C
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0135 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.733 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         17 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT971_ALERT_2_C Check Calcd Residual Density  0.82A From    Se1B       2.30 eA-3
PLAT971_ALERT_2_C Check Calcd Residual Density  0.79A From      I1       2.11 eA-3
PLAT971_ALERT_2_C Check Calcd Residual Density  0.86A From      I3       2.07 eA-3
PLAT971_ALERT_2_C Check Calcd Residual Density  0.85A From      I4       1.83 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  0.54A From      I6      -2.44 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  0.48A From      I6      -2.39 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  0.51A From      I3      -1.99 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on     H6D      -0.49 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H12H      -0.55 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.74 mm
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      36.60 Why ?
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note

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

   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker (1997); cell refinement: SAINT (Bruker (1997); data reduction: SAINT (Bruker (1997); program(s) used to solve structure: SIR2004 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

3-Methyl-4,5,6,7,8,9-hexahydrocycloocta[d][1,2,3]selenadiazol]-3-ium iodide triiodide (3/2/1)

Crystal data

3C9H15N2Se^+·I3^−·2I^−	F(000) = 1232
Mr = 1325.07	Dx = 2.224 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 7.2438 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.9980 (8) Å	Cell parameters from 9806 reflections
c = 20.1035 (11) Å	θ = 2.4–27.9°
α = 81.913 (2)°	µ = 6.72 mm^−1
β = 86.409 (2)°	T = 173 K
γ = 78.801 (2)°	Plate, brown
V = 1978.46 (19) Å^3	0.74 × 0.34 × 0.05 mm
Z = 2

Data collection

Bruker SMART APEX2 diffractometer	9472 independent reflections
Radiation source: sealed Tube	8038 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
CCD scan	θmax = 27.9°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.095, Tmax = 0.810	k = −18→18
64010 measured reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0374P)^2 + 36.6012P] where P = (Fo^2 + 2Fc^2)/3
9472 reflections	(Δ/σ)max = 0.001
376 parameters	Δρmax = 3.41 e Å^−3
0 restraints	Δρmin = −2.67 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Se1A	−0.19773 (12)	0.77479 (6)	0.32688 (4)	0.02677 (18)
N2A	−0.1532 (11)	0.8825 (5)	0.3593 (4)	0.0280 (15)
N3A	0.0154 (10)	0.8599 (5)	0.3836 (4)	0.0260 (15)
C4A	0.1281 (12)	0.7720 (6)	0.3791 (4)	0.0261 (17)
C5A	0.3182 (12)	0.7445 (7)	0.4088 (5)	0.0302 (19)
H5A	0.374675	0.804114	0.405033	0.036*
H5B	0.399634	0.697554	0.381973	0.036*
C6A	0.3181 (13)	0.6989 (7)	0.4819 (5)	0.035 (2)
H6A	0.261513	0.750555	0.509917	0.042*
H6B	0.450164	0.675027	0.495058	0.042*
C7A	0.2097 (14)	0.6121 (7)	0.4978 (5)	0.034 (2)
H7A	0.226613	0.584570	0.545598	0.040*
H7B	0.073816	0.638640	0.492167	0.040*
C8A	0.2688 (14)	0.5273 (7)	0.4544 (5)	0.037 (2)
H8A	0.279913	0.464019	0.484315	0.044*
H8B	0.394947	0.531190	0.433428	0.044*
C9A	0.1315 (14)	0.5272 (7)	0.3982 (5)	0.035 (2)
H9A	0.162767	0.462572	0.381488	0.042*
H9B	0.002360	0.533559	0.418548	0.042*
C10A	0.1303 (12)	0.6081 (7)	0.3372 (5)	0.0300 (18)
H10A	0.261990	0.608223	0.320790	0.036*
H10B	0.062713	0.590546	0.300727	0.036*
C11A	0.0417 (11)	0.7103 (6)	0.3501 (4)	0.0230 (16)
C12A	0.0779 (15)	0.9412 (7)	0.4105 (5)	0.035 (2)
H12A	0.175533	0.964714	0.380199	0.053*
H12B	0.128929	0.917515	0.455104	0.053*
H12C	−0.029551	0.995140	0.414068	0.053*
Se1B	1.21598 (11)	0.73576 (6)	0.16638 (4)	0.02384 (17)
N2B	1.1750 (9)	0.6258 (5)	0.1369 (4)	0.0240 (14)
N3B	1.0036 (9)	0.6393 (5)	0.1162 (3)	0.0199 (13)
C4B	0.8875 (11)	0.7294 (6)	0.1200 (4)	0.0238 (16)
C5B	0.6933 (11)	0.7517 (6)	0.0947 (5)	0.0265 (17)
H5C	0.613381	0.799480	0.121370	0.032*
H5D	0.640456	0.690831	0.101318	0.032*
C6B	0.6870 (14)	0.7947 (7)	0.0190 (5)	0.036 (2)
H6C	0.746374	0.741910	−0.007743	0.043*
H6D	0.553481	0.814355	0.006687	0.043*
C7B	0.7817 (14)	0.8813 (7)	−0.0010 (5)	0.0327 (19)
H7C	0.753979	0.906879	−0.048488	0.039*
H7D	0.919476	0.857741	0.001150	0.039*
C8B	0.7278 (13)	0.9675 (7)	0.0408 (5)	0.0303 (19)
H8C	0.708259	1.029589	0.009518	0.036*
H8D	0.606017	0.962390	0.064946	0.036*
C9B	0.8711 (12)	0.9740 (6)	0.0924 (4)	0.0273 (17)
H9C	0.997699	0.966334	0.069923	0.033*
H9D	0.841455	1.040638	0.106164	0.033*
C10B	0.8797 (11)	0.8990 (6)	0.1557 (4)	0.0234 (16)
H10C	0.949369	0.920714	0.189849	0.028*
H10D	0.749787	0.898269	0.174011	0.028*
C11B	0.9722 (11)	0.7956 (6)	0.1450 (4)	0.0207 (15)
C12B	0.9456 (14)	0.5560 (7)	0.0915 (5)	0.033 (2)
H12D	1.054861	0.502759	0.088906	0.050*
H12E	0.894350	0.577125	0.046678	0.050*
H12F	0.848982	0.532511	0.122332	0.050*
Se1C	0.40931 (14)	0.44524 (7)	0.21655 (5)	0.0337 (2)
N2C	0.2961 (11)	0.3728 (6)	0.1706 (4)	0.0312 (16)
N3C	0.3370 (10)	0.2803 (5)	0.1976 (4)	0.0271 (15)
C4C	0.4462 (12)	0.2538 (6)	0.2531 (4)	0.0258 (17)
C5C	0.4998 (13)	0.1494 (6)	0.2839 (4)	0.0297 (18)
H5E	0.395430	0.114562	0.279766	0.036*
H5F	0.520468	0.147235	0.332371	0.036*
C6C	0.6789 (14)	0.0972 (7)	0.2500 (5)	0.039 (2)
H6E	0.647724	0.086074	0.204782	0.046*
H6F	0.719466	0.032028	0.276371	0.046*
C7C	0.8449 (14)	0.1516 (8)	0.2423 (6)	0.041 (2)
H7E	0.813469	0.211196	0.209141	0.050*
H7F	0.956168	0.108806	0.224006	0.050*
C8C	0.8968 (16)	0.1819 (9)	0.3080 (6)	0.048 (3)
H8E	1.034891	0.162552	0.312322	0.058*
H8F	0.836955	0.144455	0.345946	0.058*
C9C	0.8386 (16)	0.2934 (7)	0.3147 (6)	0.043 (3)
H9E	0.911668	0.308138	0.350708	0.051*
H9F	0.874475	0.331420	0.272119	0.051*
C10C	0.6295 (14)	0.3290 (7)	0.3303 (5)	0.036 (2)
H10E	0.588918	0.284786	0.368991	0.043*
H10F	0.612445	0.395417	0.344016	0.043*
C11C	0.5052 (13)	0.3329 (7)	0.2735 (4)	0.0295 (18)
C12C	0.2703 (15)	0.2090 (7)	0.1611 (5)	0.037 (2)
H12G	0.133439	0.227198	0.157111	0.056*
H12H	0.302298	0.142946	0.186038	0.056*
H12I	0.331139	0.209767	0.116168	0.056*
I1	0.74529 (9)	0.31836 (5)	0.05629 (3)	0.03944 (16)
I2	0.500000	0.500000	0.000000	0.02823 (17)
I4	0.24632 (9)	0.18708 (5)	0.45955 (3)	0.04046 (17)
I5	0.500000	0.000000	0.500000	0.0348 (2)
I3	0.33131 (8)	0.92120 (4)	0.23051 (3)	0.03323 (15)
I6	0.67814 (9)	0.58573 (5)	0.26699 (4)	0.03840 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1A	0.0252 (4)	0.0255 (4)	0.0271 (4)	0.0002 (3)	−0.0019 (3)	−0.0016 (3)
N2A	0.042 (4)	0.015 (3)	0.025 (3)	−0.002 (3)	−0.001 (3)	0.002 (3)
N3A	0.030 (4)	0.023 (3)	0.024 (3)	−0.006 (3)	0.001 (3)	−0.002 (3)
C4A	0.025 (4)	0.020 (4)	0.033 (4)	−0.004 (3)	0.007 (3)	−0.003 (3)
C5A	0.018 (4)	0.032 (5)	0.042 (5)	−0.007 (3)	0.002 (3)	−0.007 (4)
C6A	0.026 (4)	0.037 (5)	0.041 (5)	−0.004 (4)	−0.015 (4)	−0.001 (4)
C7A	0.036 (5)	0.031 (5)	0.029 (4)	0.000 (4)	−0.002 (4)	0.005 (4)
C8A	0.030 (5)	0.034 (5)	0.042 (5)	0.002 (4)	−0.006 (4)	−0.002 (4)
C9A	0.035 (5)	0.025 (4)	0.042 (5)	−0.004 (4)	0.001 (4)	−0.001 (4)
C10A	0.023 (4)	0.033 (5)	0.033 (5)	0.001 (3)	0.002 (3)	−0.010 (4)
C11A	0.021 (4)	0.025 (4)	0.020 (4)	−0.004 (3)	0.006 (3)	0.003 (3)
C12A	0.045 (6)	0.020 (4)	0.042 (5)	−0.010 (4)	−0.004 (4)	−0.004 (4)
Se1B	0.0184 (4)	0.0231 (4)	0.0285 (4)	0.0008 (3)	−0.0026 (3)	−0.0037 (3)
N2B	0.018 (3)	0.021 (3)	0.030 (4)	0.002 (3)	0.001 (3)	−0.004 (3)
N3B	0.020 (3)	0.018 (3)	0.024 (3)	−0.008 (3)	−0.002 (2)	−0.001 (2)
C4B	0.021 (4)	0.025 (4)	0.023 (4)	−0.001 (3)	0.000 (3)	−0.002 (3)
C5B	0.019 (4)	0.023 (4)	0.037 (5)	−0.002 (3)	−0.003 (3)	−0.003 (3)
C6B	0.035 (5)	0.034 (5)	0.036 (5)	−0.003 (4)	−0.012 (4)	−0.001 (4)
C7B	0.036 (5)	0.032 (5)	0.027 (4)	−0.002 (4)	−0.003 (4)	0.001 (4)
C8B	0.028 (4)	0.026 (4)	0.030 (4)	0.007 (3)	−0.003 (3)	0.003 (3)
C9B	0.025 (4)	0.023 (4)	0.031 (4)	0.002 (3)	0.001 (3)	−0.003 (3)
C10B	0.021 (4)	0.021 (4)	0.026 (4)	0.002 (3)	0.004 (3)	−0.003 (3)
C11B	0.017 (4)	0.022 (4)	0.019 (3)	0.003 (3)	0.004 (3)	0.001 (3)
C12B	0.031 (5)	0.026 (4)	0.044 (5)	−0.003 (4)	−0.003 (4)	−0.014 (4)
Se1C	0.0388 (5)	0.0218 (4)	0.0387 (5)	0.0037 (4)	−0.0162 (4)	−0.0038 (4)
N2C	0.034 (4)	0.027 (4)	0.032 (4)	−0.004 (3)	−0.012 (3)	0.001 (3)
N3C	0.028 (4)	0.025 (4)	0.028 (4)	−0.003 (3)	−0.006 (3)	−0.004 (3)
C4C	0.025 (4)	0.028 (4)	0.021 (4)	0.001 (3)	−0.002 (3)	−0.003 (3)
C5C	0.038 (5)	0.027 (4)	0.022 (4)	−0.001 (4)	−0.005 (3)	0.001 (3)
C6C	0.039 (5)	0.029 (5)	0.044 (6)	0.007 (4)	−0.005 (4)	−0.010 (4)
C7C	0.031 (5)	0.038 (5)	0.050 (6)	0.006 (4)	0.000 (4)	−0.008 (5)
C8C	0.036 (6)	0.049 (7)	0.054 (7)	0.010 (5)	−0.015 (5)	−0.010 (5)
C9C	0.052 (6)	0.030 (5)	0.043 (6)	0.003 (4)	−0.023 (5)	0.000 (4)
C10C	0.042 (5)	0.035 (5)	0.031 (5)	−0.002 (4)	−0.015 (4)	−0.007 (4)
C11C	0.030 (4)	0.030 (4)	0.027 (4)	0.001 (4)	−0.004 (3)	−0.007 (3)
C12C	0.046 (6)	0.032 (5)	0.037 (5)	−0.013 (4)	−0.012 (4)	−0.005 (4)
I1	0.0347 (3)	0.0381 (3)	0.0390 (3)	0.0032 (3)	−0.0030 (3)	0.0041 (3)
I2	0.0236 (4)	0.0337 (4)	0.0250 (4)	−0.0022 (3)	0.0000 (3)	−0.0005 (3)
I4	0.0324 (3)	0.0504 (4)	0.0351 (3)	−0.0014 (3)	0.0037 (2)	−0.0050 (3)
I5	0.0231 (4)	0.0508 (5)	0.0319 (4)	−0.0064 (4)	0.0006 (3)	−0.0120 (4)
I3	0.0282 (3)	0.0291 (3)	0.0442 (3)	−0.0070 (2)	0.0031 (2)	−0.0107 (2)
I6	0.0360 (3)	0.0374 (3)	0.0461 (4)	−0.0137 (3)	0.0014 (3)	−0.0117 (3)

Geometric parameters (Å, º)

Se1A—N2A	1.815 (7)	C7B—H7D	0.9900
Se1A—C11A	1.848 (8)	C8B—C9B	1.536 (13)
N2A—N3A	1.308 (11)	C8B—H8C	0.9900
N3A—C4A	1.350 (11)	C8B—H8D	0.9900
N3A—C12A	1.482 (11)	C9B—C10B	1.528 (12)
C4A—C11A	1.369 (12)	C9B—H9C	0.9900
C4A—C5A	1.495 (12)	C9B—H9D	0.9900
C5A—C6A	1.517 (13)	C10B—C11B	1.511 (10)
C5A—H5A	0.9900	C10B—H10C	0.9900
C5A—H5B	0.9900	C10B—H10D	0.9900
C6A—C7A	1.556 (14)	C12B—H12D	0.9800
C6A—H6A	0.9900	C12B—H12E	0.9800
C6A—H6B	0.9900	C12B—H12F	0.9800
C7A—C8A	1.550 (14)	Se1C—N2C	1.798 (8)
C7A—H7A	0.9900	Se1C—C11C	1.853 (9)
C7A—H7B	0.9900	N2C—N3C	1.315 (10)
C8A—C9A	1.551 (14)	N3C—C4C	1.375 (11)
C8A—H8A	0.9900	N3C—C12C	1.484 (11)
C8A—H8B	0.9900	C4C—C11C	1.382 (13)
C9A—C10A	1.547 (13)	C4C—C5C	1.491 (12)
C9A—H9A	0.9900	C5C—C6C	1.531 (13)
C9A—H9B	0.9900	C5C—H5E	0.9900
C10A—C11A	1.501 (12)	C5C—H5F	0.9900
C10A—H10A	0.9900	C6C—C7C	1.533 (15)
C10A—H10B	0.9900	C6C—H6E	0.9900
C12A—H12A	0.9800	C6C—H6F	0.9900
C12A—H12B	0.9800	C7C—C8C	1.533 (15)
C12A—H12C	0.9800	C7C—H7E	0.9900
Se1B—N2B	1.806 (7)	C7C—H7F	0.9900
Se1B—C11B	1.851 (8)	C8C—C9C	1.558 (15)
N2B—N3B	1.305 (9)	C8C—H8E	0.9900
N3B—C4B	1.382 (10)	C8C—H8F	0.9900
N3B—C12B	1.471 (10)	C9C—C10C	1.527 (15)
C4B—C11B	1.371 (12)	C9C—H9E	0.9900
C4B—C5B	1.486 (11)	C9C—H9F	0.9900
C5B—C6B	1.557 (13)	C10C—C11C	1.487 (12)
C5B—H5C	0.9900	C10C—H10E	0.9900
C5B—H5D	0.9900	C10C—H10F	0.9900
C6B—C7B	1.501 (14)	C12C—H12G	0.9800
C6B—H6C	0.9900	C12C—H12H	0.9800
C6B—H6D	0.9900	C12C—H12I	0.9800
C7B—C8B	1.541 (13)	I1—I2	2.9309 (6)
C7B—H7C	0.9900	I4—I5	2.9351 (7)
N2A—Se1A—C11A	89.1 (4)	C7B—C8B—H8C	108.3
N3A—N2A—Se1A	107.4 (5)	C9B—C8B—H8D	108.3
N2A—N3A—C4A	122.1 (7)	C7B—C8B—H8D	108.3
N2A—N3A—C12A	114.7 (7)	H8C—C8B—H8D	107.4
C4A—N3A—C12A	123.0 (8)	C10B—C9B—C8B	116.0 (8)
N3A—C4A—C11A	112.3 (8)	C10B—C9B—H9C	108.3
N3A—C4A—C5A	122.3 (8)	C8B—C9B—H9C	108.3
C11A—C4A—C5A	125.1 (8)	C10B—C9B—H9D	108.3
C4A—C5A—C6A	114.6 (7)	C8B—C9B—H9D	108.3
C4A—C5A—H5A	108.6	H9C—C9B—H9D	107.4
C6A—C5A—H5A	108.6	C11B—C10B—C9B	114.5 (7)
C4A—C5A—H5B	108.6	C11B—C10B—H10C	108.6
C6A—C5A—H5B	108.6	C9B—C10B—H10C	108.6
H5A—C5A—H5B	107.6	C11B—C10B—H10D	108.6
C5A—C6A—C7A	114.9 (8)	C9B—C10B—H10D	108.6
C5A—C6A—H6A	108.6	H10C—C10B—H10D	107.6
C7A—C6A—H6A	108.6	C4B—C11B—C10B	125.7 (7)
C5A—C6A—H6B	108.6	C4B—C11B—Se1B	108.6 (6)
C7A—C6A—H6B	108.6	C10B—C11B—Se1B	125.7 (6)
H6A—C6A—H6B	107.5	N3B—C12B—H12D	109.5
C8A—C7A—C6A	115.9 (8)	N3B—C12B—H12E	109.5
C8A—C7A—H7A	108.3	H12D—C12B—H12E	109.5
C6A—C7A—H7A	108.3	N3B—C12B—H12F	109.5
C8A—C7A—H7B	108.3	H12D—C12B—H12F	109.5
C6A—C7A—H7B	108.3	H12E—C12B—H12F	109.5
H7A—C7A—H7B	107.4	N2C—Se1C—C11C	89.6 (4)
C7A—C8A—C9A	114.6 (8)	N3C—N2C—Se1C	108.9 (5)
C7A—C8A—H8A	108.6	N2C—N3C—C4C	120.4 (7)
C9A—C8A—H8A	108.6	N2C—N3C—C12C	115.6 (7)
C7A—C8A—H8B	108.6	C4C—N3C—C12C	123.9 (8)
C9A—C8A—H8B	108.6	N3C—C4C—C11C	112.5 (8)
H8A—C8A—H8B	107.6	N3C—C4C—C5C	121.9 (8)
C10A—C9A—C8A	116.5 (8)	C11C—C4C—C5C	125.5 (8)
C10A—C9A—H9A	108.2	C4C—C5C—C6C	111.5 (8)
C8A—C9A—H9A	108.2	C4C—C5C—H5E	109.3
C10A—C9A—H9B	108.2	C6C—C5C—H5E	109.3
C8A—C9A—H9B	108.2	C4C—C5C—H5F	109.3
H9A—C9A—H9B	107.3	C6C—C5C—H5F	109.3
C11A—C10A—C9A	115.7 (7)	H5E—C5C—H5F	108.0
C11A—C10A—H10A	108.4	C5C—C6C—C7C	115.5 (8)
C9A—C10A—H10A	108.4	C5C—C6C—H6E	108.4
C11A—C10A—H10B	108.4	C7C—C6C—H6E	108.4
C9A—C10A—H10B	108.4	C5C—C6C—H6F	108.4
H10A—C10A—H10B	107.4	C7C—C6C—H6F	108.4
C4A—C11A—C10A	125.3 (8)	H6E—C6C—H6F	107.5
C4A—C11A—Se1A	109.0 (6)	C6C—C7C—C8C	113.9 (10)
C10A—C11A—Se1A	125.7 (6)	C6C—C7C—H7E	108.8
N3A—C12A—H12A	109.5	C8C—C7C—H7E	108.8
N3A—C12A—H12B	109.5	C6C—C7C—H7F	108.8
H12A—C12A—H12B	109.5	C8C—C7C—H7F	108.8
N3A—C12A—H12C	109.5	H7E—C7C—H7F	107.7
H12A—C12A—H12C	109.5	C7C—C8C—C9C	115.5 (9)
H12B—C12A—H12C	109.5	C7C—C8C—H8E	108.4
N2B—Se1B—C11B	88.9 (3)	C9C—C8C—H8E	108.4
N3B—N2B—Se1B	110.2 (5)	C7C—C8C—H8F	108.4
N2B—N3B—C4B	118.5 (7)	C9C—C8C—H8F	108.4
N2B—N3B—C12B	117.3 (7)	H8E—C8C—H8F	107.5
C4B—N3B—C12B	124.2 (7)	C10C—C9C—C8C	115.3 (10)
C11B—C4B—N3B	113.8 (7)	C10C—C9C—H9E	108.5
C11B—C4B—C5B	124.4 (7)	C8C—C9C—H9E	108.5
N3B—C4B—C5B	121.6 (7)	C10C—C9C—H9F	108.5
C4B—C5B—C6B	112.5 (7)	C8C—C9C—H9F	108.5
C4B—C5B—H5C	109.1	H9E—C9C—H9F	107.5
C6B—C5B—H5C	109.1	C11C—C10C—C9C	114.5 (8)
C4B—C5B—H5D	109.1	C11C—C10C—H10E	108.6
C6B—C5B—H5D	109.1	C9C—C10C—H10E	108.6
H5C—C5B—H5D	107.8	C11C—C10C—H10F	108.6
C7B—C6B—C5B	115.9 (8)	C9C—C10C—H10F	108.6
C7B—C6B—H6C	108.3	H10E—C10C—H10F	107.6
C5B—C6B—H6C	108.3	C4C—C11C—C10C	126.0 (8)
C7B—C6B—H6D	108.3	C4C—C11C—Se1C	108.7 (6)
C5B—C6B—H6D	108.3	C10C—C11C—Se1C	125.2 (7)
H6C—C6B—H6D	107.4	N3C—C12C—H12G	109.5
C6B—C7B—C8B	116.9 (8)	N3C—C12C—H12H	109.5
C6B—C7B—H7C	108.1	H12G—C12C—H12H	109.5
C8B—C7B—H7C	108.1	N3C—C12C—H12I	109.5
C6B—C7B—H7D	108.1	H12G—C12C—H12I	109.5
C8B—C7B—H7D	108.1	H12H—C12C—H12I	109.5
H7C—C7B—H7D	107.3	I1^i—I2—I1	180.0
C9B—C8B—C7B	115.7 (7)	I4—I5—I4^ii	180.0
C9B—C8B—H8C	108.3
C11A—Se1A—N2A—N3A	−2.1 (6)	C6B—C7B—C8B—C9B	102.4 (10)
Se1A—N2A—N3A—C4A	3.5 (10)	C7B—C8B—C9B—C10B	−74.5 (10)
Se1A—N2A—N3A—C12A	178.2 (6)	C8B—C9B—C10B—C11B	73.3 (9)
N2A—N3A—C4A—C11A	−3.3 (12)	N3B—C4B—C11B—C10B	−179.1 (7)
C12A—N3A—C4A—C11A	−177.5 (8)	C5B—C4B—C11B—C10B	4.7 (13)
N2A—N3A—C4A—C5A	−177.9 (8)	N3B—C4B—C11B—Se1B	−1.3 (9)
C12A—N3A—C4A—C5A	7.9 (13)	C5B—C4B—C11B—Se1B	−177.4 (7)
N3A—C4A—C5A—C6A	87.2 (10)	C9B—C10B—C11B—C4B	−81.2 (10)
C11A—C4A—C5A—C6A	−86.7 (11)	C9B—C10B—C11B—Se1B	101.4 (8)
C4A—C5A—C6A—C7A	50.6 (11)	N2B—Se1B—C11B—C4B	1.0 (6)
C5A—C6A—C7A—C8A	53.8 (11)	N2B—Se1B—C11B—C10B	178.8 (7)
C6A—C7A—C8A—C9A	−103.0 (10)	C11C—Se1C—N2C—N3C	−1.1 (7)
C7A—C8A—C9A—C10A	72.2 (11)	Se1C—N2C—N3C—C4C	1.7 (10)
C8A—C9A—C10A—C11A	−72.0 (11)	Se1C—N2C—N3C—C12C	−173.9 (7)
N3A—C4A—C11A—C10A	179.2 (8)	N2C—N3C—C4C—C11C	−1.4 (12)
C5A—C4A—C11A—C10A	−6.4 (14)	C12C—N3C—C4C—C11C	173.8 (9)
N3A—C4A—C11A—Se1A	1.2 (9)	N2C—N3C—C4C—C5C	−178.3 (8)
C5A—C4A—C11A—Se1A	175.6 (7)	C12C—N3C—C4C—C5C	−3.1 (13)
C9A—C10A—C11A—C4A	81.1 (11)	N3C—C4C—C5C—C6C	86.5 (11)
C9A—C10A—C11A—Se1A	−101.2 (9)	C11C—C4C—C5C—C6C	−90.0 (11)
N2A—Se1A—C11A—C4A	0.5 (6)	C4C—C5C—C6C—C7C	49.6 (11)
N2A—Se1A—C11A—C10A	−177.5 (7)	C5C—C6C—C7C—C8C	53.0 (12)
C11B—Se1B—N2B—N3B	−0.4 (6)	C6C—C7C—C8C—C9C	−105.9 (12)
Se1B—N2B—N3B—C4B	−0.3 (9)	C7C—C8C—C9C—C10C	75.8 (13)
Se1B—N2B—N3B—C12B	−179.0 (6)	C8C—C9C—C10C—C11C	−71.6 (12)
N2B—N3B—C4B—C11B	1.1 (11)	N3C—C4C—C11C—C10C	−178.0 (9)
C12B—N3B—C4B—C11B	179.7 (8)	C5C—C4C—C11C—C10C	−1.2 (15)
N2B—N3B—C4B—C5B	177.3 (7)	N3C—C4C—C11C—Se1C	0.4 (9)
C12B—N3B—C4B—C5B	−4.0 (12)	C5C—C4C—C11C—Se1C	177.2 (7)
C11B—C4B—C5B—C6B	87.3 (10)	C9C—C10C—C11C—C4C	78.5 (13)
N3B—C4B—C5B—C6B	−88.5 (10)	C9C—C10C—C11C—Se1C	−99.6 (10)
C4B—C5B—C6B—C7B	−52.3 (11)	N2C—Se1C—C11C—C4C	0.4 (7)
C5B—C6B—C7B—C8B	−50.7 (11)	N2C—Se1C—C11C—C10C	178.7 (9)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z+1.