Tetra­kis(N-ethyl-9-oxo-4-azonia-5-aza-9H-fluorene) tetra-μ₃-iodo-hexa-μ₂-iodo-dodeca­iodo­hexa­bismuthate

The new iodo­bismuthate compound (C₁₃H₁₁N₂O)₄[Bi₆I₂₂] has been synthesized solvothermally by reacting BiI₃, Zn(NO₃)₂·6H₂O and 4,5-diaza­fluoren-9-one in a water/ethanol solvent mixture. The asymmetric unit of the compound contains two independent [N-ethyl-4,5-dafo]⁺ cations and one-half of a centrosymmetric [Bi₆I₂₂]⁴⁻ anion. The average terminal Bi—I, Bi—μ₂-I and Bi—μ₃-I bond lengths in the anion are 2.8923 (2), 3.1403 (2) and 3.3022 (2) Å, respectively.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.035
• wR factor = 0.076
• Data-to-parameter ratio = 23.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact  H12A   ..  H12A    ..       2.05 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi1    -   I2      ..       7.27 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi1    -   I5      ..       6.85 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi2    -   I10     ..       8.08 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi2    -   I10_a   ..       8.89 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi3    -   I6      ..       8.42 su
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Tetrakis(N-ethyl-9-oxo-4-azonia-5-aza-9H-fluorene) tetra-µ₃-iodo-hexa-µ₂-iodo-dodecaiodohexabismuthate

Crystal data

(C13H11N2O)4[Bi6I22]	F(000) = 8432
Mr = 4890.63	Dx = 3.492 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5414 reflections
a = 13.3944 (10) Å	θ = 2.2–26.4°
b = 17.0764 (12) Å	µ = 18.65 mm^−1
c = 40.710 (3) Å	T = 150 K
β = 92.589 (1)°	Plate, orange
V = 9302.1 (12) Å^3	0.14 × 0.08 × 0.04 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	9574 independent reflections
Radiation source: fine-focus sealed tube	8178 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω scans	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.180, Tmax = 0.474	k = −21→20
48604 measured reflections	l = −50→50

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0257P)^2 + 84.5173P] where P = (Fo^2 + 2Fc^2)/3
9574 reflections	(Δ/σ)max = 0.002
417 parameters	Δρmax = 1.13 e Å^−3
0 restraints	Δρmin = −0.92 e Å^−3

Special details

Experimental. Crystal red at 294 K, becomes lighter red / orange at lower T

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Bi1	0.58269 (2)	0.559959 (19)	0.357488 (7)	0.02597 (8)
Bi2	0.63654 (2)	0.555310 (18)	0.470898 (7)	0.02425 (8)
Bi3	0.31254 (2)	0.457963 (18)	0.417111 (7)	0.02355 (8)
I1	0.79551 (4)	0.53826 (4)	0.354655 (15)	0.03777 (15)
I2	0.56134 (5)	0.69102 (4)	0.310694 (15)	0.03752 (14)
I3	0.54283 (4)	0.43512 (4)	0.309781 (14)	0.03658 (14)
I4	0.84414 (4)	0.52351 (4)	0.463371 (15)	0.03879 (15)
I5	0.62568 (4)	0.68141 (3)	0.420556 (13)	0.03232 (13)
I6	0.56516 (4)	0.43168 (3)	0.416030 (12)	0.02507 (11)
I7	0.33888 (4)	0.58307 (3)	0.366416 (14)	0.02981 (13)
I8	0.27153 (5)	0.33928 (3)	0.368140 (14)	0.03507 (14)
I9	0.67730 (4)	0.67088 (3)	0.526158 (13)	0.03045 (13)
I10	0.61359 (4)	0.41704 (3)	0.523267 (13)	0.02576 (12)
I11	0.10666 (4)	0.49779 (4)	0.424419 (16)	0.03953 (15)
C1	0.8461 (7)	0.4302 (6)	0.2707 (2)	0.043 (2)
C2	0.7875 (7)	0.4980 (5)	0.2574 (2)	0.036 (2)
C3	0.6959 (7)	0.5018 (7)	0.2401 (2)	0.044 (2)
H3	0.6582	0.4558	0.2353	0.052*
C4	0.6616 (7)	0.5742 (6)	0.2300 (2)	0.046 (2)
H4	0.5993	0.5784	0.2180	0.055*
C5	0.7159 (7)	0.6397 (6)	0.2371 (2)	0.042 (2)
H5	0.6903	0.6891	0.2301	0.051*
C6	0.8410 (7)	0.5666 (5)	0.2644 (2)	0.033 (2)
C7	0.9363 (7)	0.5467 (5)	0.2836 (2)	0.033 (2)
C8	1.0801 (7)	0.5628 (6)	0.3123 (2)	0.041 (2)
H8	1.1309	0.5963	0.3214	0.050*
C9	1.0906 (7)	0.4834 (6)	0.3174 (2)	0.039 (2)
H9	1.1464	0.4639	0.3302	0.047*
C10	1.0194 (7)	0.4318 (6)	0.3040 (2)	0.044 (2)
H10	1.0257	0.3767	0.3064	0.052*
C11	0.9381 (7)	0.4662 (5)	0.2867 (2)	0.035 (2)
C12	0.8627 (7)	0.7127 (6)	0.2598 (2)	0.045 (2)
H12A	0.9351	0.7013	0.2625	0.054*
H12B	0.8521	0.7473	0.2404	0.054*
C13	0.8292 (8)	0.7527 (7)	0.2892 (2)	0.053 (3)
H13A	0.7597	0.7696	0.2855	0.080*
H13B	0.8716	0.7986	0.2938	0.080*
H13C	0.8341	0.7168	0.3080	0.080*
C14	0.6761 (7)	0.2519 (5)	0.3492 (2)	0.035 (2)
C15	0.6038 (7)	0.2304 (5)	0.3745 (2)	0.032 (2)
C16	0.5075 (7)	0.2048 (5)	0.3709 (2)	0.036 (2)
H16	0.4759	0.1978	0.3497	0.044*
C17	0.4572 (7)	0.1893 (5)	0.3994 (2)	0.039 (2)
H17	0.3893	0.1730	0.3978	0.047*
C18	0.5056 (7)	0.1974 (5)	0.4298 (2)	0.035 (2)
H18	0.4710	0.1846	0.4489	0.042*
C19	0.6500 (6)	0.2412 (4)	0.40585 (19)	0.0266 (18)
C20	0.7498 (6)	0.2749 (5)	0.4021 (2)	0.0307 (19)
C21	0.9030 (7)	0.3239 (6)	0.4158 (2)	0.043 (2)
H21	0.9523	0.3397	0.4319	0.052*
C22	0.9241 (7)	0.3336 (5)	0.3827 (2)	0.042 (2)
H22	0.9862	0.3553	0.3769	0.050*
C23	0.8536 (7)	0.3113 (5)	0.3584 (2)	0.041 (2)
H23	0.8666	0.3156	0.3357	0.050*
C24	0.7636 (7)	0.2827 (5)	0.3687 (2)	0.0291 (19)
C25	0.6501 (8)	0.2301 (6)	0.4660 (2)	0.043 (2)
H25A	0.6600	0.2864	0.4709	0.051*
H25B	0.7171	0.2057	0.4655	0.051*
C26	0.5954 (8)	0.1937 (7)	0.4938 (2)	0.053 (3)
H26A	0.5310	0.2201	0.4959	0.080*
H26B	0.6356	0.1993	0.5144	0.080*
H26C	0.5840	0.1379	0.4893	0.080*
N1	0.8055 (5)	0.6368 (4)	0.25404 (17)	0.0353 (17)
N2	1.0033 (5)	0.5959 (5)	0.29533 (18)	0.0373 (18)
N3	0.6012 (5)	0.2231 (4)	0.43306 (16)	0.0298 (16)
N4	0.8167 (5)	0.2935 (4)	0.42615 (19)	0.0364 (18)
O1	0.8248 (5)	0.3621 (4)	0.26904 (18)	0.0543 (19)
O2	0.6672 (5)	0.2446 (4)	0.31998 (14)	0.0433 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Bi1	0.02548 (16)	0.02896 (18)	0.02360 (15)	−0.00162 (12)	0.00239 (12)	0.00028 (13)
Bi2	0.02329 (16)	0.02715 (17)	0.02249 (15)	−0.00182 (12)	0.00305 (12)	0.00045 (12)
Bi3	0.02263 (16)	0.02452 (16)	0.02355 (15)	−0.00060 (12)	0.00148 (12)	0.00050 (12)
I1	0.0253 (3)	0.0540 (4)	0.0344 (3)	−0.0003 (3)	0.0057 (2)	−0.0060 (3)
I2	0.0447 (3)	0.0323 (3)	0.0359 (3)	−0.0038 (3)	0.0052 (3)	0.0058 (3)
I3	0.0393 (3)	0.0337 (3)	0.0363 (3)	0.0004 (2)	−0.0034 (3)	−0.0071 (3)
I4	0.0251 (3)	0.0498 (4)	0.0420 (3)	0.0033 (3)	0.0079 (2)	0.0026 (3)
I5	0.0437 (3)	0.0276 (3)	0.0256 (3)	−0.0050 (2)	0.0011 (2)	0.0023 (2)
I6	0.0260 (3)	0.0235 (3)	0.0258 (3)	0.0023 (2)	0.0015 (2)	−0.0010 (2)
I7	0.0265 (3)	0.0286 (3)	0.0344 (3)	0.0019 (2)	0.0028 (2)	0.0086 (2)
I8	0.0480 (4)	0.0272 (3)	0.0296 (3)	−0.0008 (2)	−0.0023 (3)	−0.0035 (2)
I9	0.0429 (3)	0.0246 (3)	0.0239 (3)	−0.0056 (2)	0.0021 (2)	0.0007 (2)
I10	0.0265 (3)	0.0233 (3)	0.0275 (3)	0.0002 (2)	0.0024 (2)	−0.0013 (2)
I11	0.0238 (3)	0.0431 (4)	0.0521 (4)	0.0022 (2)	0.0061 (3)	−0.0049 (3)
C1	0.041 (6)	0.044 (6)	0.043 (6)	0.000 (5)	0.012 (4)	−0.002 (5)
C2	0.035 (5)	0.036 (5)	0.036 (5)	0.001 (4)	0.014 (4)	−0.008 (4)
C3	0.047 (6)	0.062 (7)	0.022 (4)	−0.008 (5)	0.002 (4)	−0.009 (5)
C4	0.035 (5)	0.062 (7)	0.041 (6)	0.001 (5)	0.000 (4)	−0.004 (5)
C5	0.029 (5)	0.054 (6)	0.044 (6)	0.011 (4)	−0.003 (4)	−0.006 (5)
C6	0.037 (5)	0.042 (5)	0.021 (4)	−0.003 (4)	0.003 (4)	0.000 (4)
C7	0.040 (5)	0.036 (5)	0.022 (4)	0.001 (4)	0.006 (4)	−0.002 (4)
C8	0.032 (5)	0.060 (7)	0.033 (5)	−0.001 (5)	0.003 (4)	−0.012 (5)
C9	0.026 (5)	0.053 (6)	0.039 (5)	0.005 (4)	0.000 (4)	0.001 (5)
C10	0.048 (6)	0.049 (6)	0.034 (5)	0.005 (5)	0.007 (4)	0.010 (5)
C11	0.034 (5)	0.043 (6)	0.029 (5)	−0.002 (4)	0.001 (4)	0.010 (4)
C12	0.039 (6)	0.044 (6)	0.051 (6)	0.002 (4)	−0.002 (5)	−0.001 (5)
C13	0.054 (7)	0.061 (7)	0.046 (6)	−0.015 (5)	0.005 (5)	0.007 (5)
C14	0.048 (6)	0.028 (5)	0.028 (5)	0.010 (4)	−0.008 (4)	−0.003 (4)
C15	0.039 (5)	0.028 (5)	0.028 (4)	0.013 (4)	−0.002 (4)	0.001 (4)
C16	0.041 (5)	0.033 (5)	0.034 (5)	0.012 (4)	−0.009 (4)	−0.002 (4)
C17	0.032 (5)	0.033 (5)	0.052 (6)	0.004 (4)	0.002 (4)	−0.005 (4)
C18	0.038 (5)	0.033 (5)	0.034 (5)	0.010 (4)	0.004 (4)	0.007 (4)
C19	0.043 (5)	0.016 (4)	0.021 (4)	0.011 (3)	0.002 (4)	−0.005 (3)
C20	0.032 (5)	0.031 (5)	0.029 (4)	0.006 (4)	0.000 (4)	−0.010 (4)
C21	0.038 (5)	0.053 (6)	0.038 (5)	0.005 (5)	−0.003 (4)	−0.004 (5)
C22	0.042 (6)	0.035 (5)	0.049 (6)	0.000 (4)	0.009 (5)	−0.002 (4)
C23	0.043 (6)	0.038 (6)	0.043 (6)	0.005 (4)	−0.002 (4)	−0.005 (4)
C24	0.044 (5)	0.019 (4)	0.025 (4)	0.000 (4)	0.003 (4)	−0.004 (3)
C25	0.061 (7)	0.032 (5)	0.034 (5)	0.007 (5)	−0.004 (5)	0.000 (4)
C26	0.049 (6)	0.064 (7)	0.046 (6)	−0.018 (5)	0.000 (5)	0.001 (5)
N1	0.038 (4)	0.035 (4)	0.032 (4)	0.000 (3)	0.001 (3)	−0.001 (3)
N2	0.030 (4)	0.051 (5)	0.031 (4)	0.002 (3)	0.003 (3)	−0.011 (4)
N3	0.032 (4)	0.030 (4)	0.028 (4)	0.010 (3)	0.001 (3)	−0.001 (3)
N4	0.031 (4)	0.033 (4)	0.045 (5)	0.004 (3)	0.004 (3)	−0.005 (4)
O1	0.057 (5)	0.040 (4)	0.065 (5)	−0.004 (3)	−0.005 (4)	0.006 (4)
O2	0.057 (4)	0.045 (4)	0.028 (3)	0.003 (3)	−0.004 (3)	−0.004 (3)

Geometric parameters (Å, º)

Bi1—I1	2.8820 (7)	C9—H9	0.9500
Bi1—I3	2.9169 (7)	C10—C11	1.399 (12)
Bi1—I2	2.9445 (7)	C10—H10	0.9500
Bi1—I6	3.2533 (6)	C12—C13	1.467 (13)
Bi1—I7	3.3257 (7)	C12—N1	1.518 (12)
Bi1—I5	3.3304 (6)	C12—H12A	0.9900
Bi2—I4	2.8632 (7)	C12—H12B	0.9900
Bi2—I5	2.9718 (6)	C13—H13A	0.9800
Bi2—I9	3.0237 (6)	C13—H13B	0.9800
Bi2—I6	3.1887 (6)	C13—H13C	0.9800
Bi2—I10	3.2053 (6)	C14—O2	1.198 (10)
Bi2—I10^i	3.4025 (6)	C14—C24	1.482 (12)
Bi3—I11	2.8687 (7)	C14—C15	1.490 (13)
Bi3—I8	2.8783 (6)	C15—C16	1.364 (12)
Bi3—I7	3.0022 (6)	C15—C19	1.404 (11)
Bi3—I9^i	3.1881 (6)	C16—C17	1.392 (13)
Bi3—I10^i	3.3479 (6)	C16—H16	0.9500
Bi3—I6	3.4156 (6)	C17—C18	1.378 (12)
I9—Bi3^i	3.1881 (6)	C17—H17	0.9500
I10—Bi3^i	3.3479 (6)	C18—N3	1.355 (11)
I10—Bi2^i	3.4024 (6)	C18—H18	0.9500
C1—O1	1.200 (11)	C19—N3	1.347 (10)
C1—C2	1.487 (13)	C19—C20	1.470 (12)
C1—C11	1.498 (13)	C20—N4	1.336 (10)
C2—C3	1.388 (12)	C20—C24	1.385 (11)
C2—C6	1.397 (12)	C21—N4	1.352 (12)
C3—C4	1.374 (14)	C21—C22	1.397 (13)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.359 (14)	C22—C23	1.390 (13)
C4—H4	0.9500	C22—H22	0.9500
C5—N1	1.357 (11)	C23—C24	1.384 (13)
C5—H5	0.9500	C23—H23	0.9500
C6—N1	1.350 (11)	C25—N3	1.470 (11)
C6—C7	1.506 (12)	C25—C26	1.512 (13)
C7—N2	1.304 (11)	C25—H25A	0.9900
C7—C11	1.381 (12)	C25—H25B	0.9900
C8—N2	1.339 (12)	C26—H26A	0.9800
C8—C9	1.379 (13)	C26—H26B	0.9800
C8—H8	0.9500	C26—H26C	0.9800
C9—C10	1.392 (13)
I1—Bi1—I3	91.780 (19)	N2—C8—H8	117.8
I1—Bi1—I2	98.00 (2)	C9—C8—H8	117.8
I3—Bi1—I2	96.62 (2)	C8—C9—C10	120.0 (9)
I1—Bi1—I6	92.696 (18)	C8—C9—H9	120.0
I3—Bi1—I6	88.772 (18)	C10—C9—H9	120.0
I2—Bi1—I6	167.845 (19)	C9—C10—C11	115.8 (10)
I1—Bi1—I7	175.988 (19)	C9—C10—H10	122.1
I3—Bi1—I7	90.477 (17)	C11—C10—H10	122.1
I2—Bi1—I7	85.029 (17)	C7—C11—C10	118.3 (9)
I6—Bi1—I7	84.035 (15)	C7—C11—C1	111.0 (8)
I1—Bi1—I5	88.513 (18)	C10—C11—C1	130.7 (9)
I3—Bi1—I5	171.314 (19)	C13—C12—N1	110.7 (8)
I2—Bi1—I5	91.938 (18)	C13—C12—H12A	109.5
I6—Bi1—I5	82.544 (16)	N1—C12—H12A	109.5
I7—Bi1—I5	88.756 (16)	C13—C12—H12B	109.5
I4—Bi2—I5	94.654 (19)	N1—C12—H12B	109.5
I4—Bi2—I9	93.431 (19)	H12A—C12—H12B	108.1
I5—Bi2—I9	92.391 (18)	C12—C13—H13A	109.5
I4—Bi2—I6	93.520 (18)	C12—C13—H13B	109.5
I5—Bi2—I6	89.590 (17)	H13A—C13—H13B	109.5
I9—Bi2—I6	172.594 (18)	C12—C13—H13C	109.5
I4—Bi2—I10	93.111 (18)	H13A—C13—H13C	109.5
I5—Bi2—I10	171.609 (18)	H13B—C13—H13C	109.5
I9—Bi2—I10	90.312 (16)	O2—C14—C24	127.6 (9)
I6—Bi2—I10	86.761 (16)	O2—C14—C15	128.5 (9)
I4—Bi2—I10^i	176.323 (19)	C24—C14—C15	103.9 (7)
I5—Bi2—I10^i	85.977 (16)	C16—C15—C19	121.0 (8)
I9—Bi2—I10^i	90.160 (16)	C16—C15—C14	130.2 (8)
I6—Bi2—I10^i	82.858 (14)	C19—C15—C14	108.8 (8)
I10—Bi2—I10^i	86.073 (15)	C15—C16—C17	117.6 (8)
I11—Bi3—I8	94.85 (2)	C15—C16—H16	121.2
I11—Bi3—I7	92.633 (19)	C17—C16—H16	121.2
I8—Bi3—I7	92.841 (19)	C18—C17—C16	120.2 (9)
I11—Bi3—I9^i	95.641 (19)	C18—C17—H17	119.9
I8—Bi3—I9^i	90.936 (18)	C16—C17—H17	119.9
I7—Bi3—I9^i	170.583 (18)	N3—C18—C17	121.7 (8)
I11—Bi3—I10^i	91.583 (18)	N3—C18—H18	119.1
I8—Bi3—I10^i	172.718 (18)	C17—C18—H18	119.1
I7—Bi3—I10^i	90.264 (17)	N3—C19—C15	120.5 (8)
I9^i—Bi3—I10^i	85.030 (16)	N3—C19—C20	130.7 (7)
I11—Bi3—I6	171.880 (19)	C15—C19—C20	108.8 (7)
I8—Bi3—I6	93.251 (17)	N4—C20—C24	125.5 (8)
I7—Bi3—I6	86.410 (15)	N4—C20—C19	126.9 (8)
I9^i—Bi3—I6	84.764 (15)	C24—C20—C19	107.6 (7)
I10^i—Bi3—I6	80.364 (14)	N4—C21—C22	124.0 (9)
Bi2—I5—Bi1	94.692 (18)	N4—C21—H21	118.0
Bi2—I6—Bi1	92.183 (16)	C22—C21—H21	118.0
Bi2—I6—Bi3	99.780 (15)	C23—C22—C21	119.5 (9)
Bi1—I6—Bi3	91.450 (14)	C23—C22—H22	120.2
Bi3—I7—Bi1	97.885 (16)	C21—C22—H22	120.2
Bi2—I9—Bi3^i	95.097 (17)	C24—C23—C22	116.9 (9)
Bi2—I10—Bi3^i	88.764 (15)	C24—C23—H23	121.5
Bi2—I10—Bi2^i	93.927 (15)	C22—C23—H23	121.5
Bi3^i—I10—Bi2^i	96.932 (15)	C23—C24—C20	119.3 (8)
O1—C1—C2	127.8 (9)	C23—C24—C14	129.9 (8)
O1—C1—C11	127.7 (9)	C20—C24—C14	110.7 (8)
C2—C1—C11	104.5 (8)	N3—C25—C26	116.0 (8)
C3—C2—C6	119.8 (9)	N3—C25—H25A	108.3
C3—C2—C1	131.5 (9)	C26—C25—H25A	108.3
C6—C2—C1	108.7 (8)	N3—C25—H25B	108.3
C4—C3—C2	118.0 (9)	C26—C25—H25B	108.3
C4—C3—H3	121.0	H25A—C25—H25B	107.4
C2—C3—H3	121.0	C25—C26—H26A	109.5
C5—C4—C3	120.5 (9)	C25—C26—H26B	109.5
C5—C4—H4	119.7	H26A—C26—H26B	109.5
C3—C4—H4	119.7	C25—C26—H26C	109.5
N1—C5—C4	122.0 (9)	H26A—C26—H26C	109.5
N1—C5—H5	119.0	H26B—C26—H26C	109.5
C4—C5—H5	119.0	C6—N1—C5	118.8 (8)
N1—C6—C2	120.8 (8)	C6—N1—C12	122.8 (7)
N1—C6—C7	129.9 (8)	C5—N1—C12	118.4 (8)
C2—C6—C7	109.4 (8)	C7—N2—C8	114.6 (8)
N2—C7—C11	126.9 (9)	C19—N3—C18	119.0 (7)
N2—C7—C6	126.7 (8)	C19—N3—C25	121.2 (8)
C11—C7—C6	106.4 (8)	C18—N3—C25	119.8 (8)
N2—C8—C9	124.4 (9)	C20—N4—C21	114.6 (8)
I4—Bi2—I5—Bi1	85.824 (19)	N1—C6—C7—N2	3.0 (15)
I9—Bi2—I5—Bi1	179.464 (17)	C2—C6—C7—N2	−177.6 (8)
I6—Bi2—I5—Bi1	−7.674 (16)	N1—C6—C7—C11	−177.8 (9)
I10^i—Bi2—I5—Bi1	−90.543 (16)	C2—C6—C7—C11	1.6 (10)
I1—Bi1—I5—Bi2	−85.329 (19)	N2—C8—C9—C10	1.5 (15)
I2—Bi1—I5—Bi2	176.714 (18)	C8—C9—C10—C11	−2.4 (13)
I6—Bi1—I5—Bi2	7.585 (16)	N2—C7—C11—C10	−0.3 (14)
I7—Bi1—I5—Bi2	91.732 (17)	C6—C7—C11—C10	−179.5 (8)
I4—Bi2—I6—Bi1	−86.801 (18)	N2—C7—C11—C1	178.2 (8)
I5—Bi2—I6—Bi1	7.837 (17)	C6—C7—C11—C1	−1.0 (10)
I10—Bi2—I6—Bi1	−179.723 (15)	C9—C10—C11—C7	1.8 (13)
I10^i—Bi2—I6—Bi1	93.833 (15)	C9—C10—C11—C1	−176.4 (9)
I4—Bi2—I6—Bi3	−178.651 (18)	O1—C1—C11—C7	179.9 (10)
I5—Bi2—I6—Bi3	−84.013 (17)	C2—C1—C11—C7	0.1 (10)
I10—Bi2—I6—Bi3	88.427 (16)	O1—C1—C11—C10	−1.8 (17)
I10^i—Bi2—I6—Bi3	1.984 (14)	C2—C1—C11—C10	178.3 (9)
I1—Bi1—I6—Bi2	81.097 (18)	O2—C14—C15—C16	−7.2 (16)
I3—Bi1—I6—Bi2	172.821 (17)	C24—C14—C15—C16	174.4 (9)
I2—Bi1—I6—Bi2	−70.58 (9)	O2—C14—C15—C19	173.4 (9)
I7—Bi1—I6—Bi2	−96.570 (16)	C24—C14—C15—C19	−5.0 (9)
I5—Bi1—I6—Bi2	−7.048 (15)	C19—C15—C16—C17	−0.5 (12)
I1—Bi1—I6—Bi3	−179.056 (17)	C14—C15—C16—C17	−179.8 (8)
I3—Bi1—I6—Bi3	−87.332 (17)	C15—C16—C17—C18	−2.1 (13)
I2—Bi1—I6—Bi3	29.27 (9)	C16—C17—C18—N3	2.4 (13)
I7—Bi1—I6—Bi3	3.277 (14)	C16—C15—C19—N3	2.9 (12)
I5—Bi1—I6—Bi3	92.799 (15)	C14—C15—C19—N3	−177.6 (7)
I8—Bi3—I6—Bi2	−178.504 (17)	C16—C15—C19—C20	−175.5 (8)
I7—Bi3—I6—Bi2	88.849 (18)	C14—C15—C19—C20	4.0 (9)
I9^i—Bi3—I6—Bi2	−87.861 (17)	N3—C19—C20—N4	2.0 (14)
I10^i—Bi3—I6—Bi2	−2.029 (15)	C15—C19—C20—N4	−179.9 (8)
I8—Bi3—I6—Bi1	89.029 (18)	N3—C19—C20—C24	−179.3 (8)
I7—Bi3—I6—Bi1	−3.617 (16)	C15—C19—C20—C24	−1.2 (9)
I9^i—Bi3—I6—Bi1	179.672 (15)	N4—C21—C22—C23	0.1 (15)
I10^i—Bi3—I6—Bi1	−94.496 (16)	C21—C22—C23—C24	2.1 (14)
I11—Bi3—I7—Bi1	175.496 (18)	C22—C23—C24—C20	−2.4 (13)
I8—Bi3—I7—Bi1	−89.511 (19)	C22—C23—C24—C14	−177.6 (8)
I10^i—Bi3—I7—Bi1	83.899 (16)	N4—C20—C24—C23	0.5 (13)
I6—Bi3—I7—Bi1	3.571 (16)	C19—C20—C24—C23	−178.2 (8)
I3—Bi1—I7—Bi3	84.95 (2)	N4—C20—C24—C14	176.6 (8)
I2—Bi1—I7—Bi3	−178.449 (19)	C19—C20—C24—C14	−2.2 (9)
I6—Bi1—I7—Bi3	−3.763 (16)	O2—C14—C24—C23	1.5 (16)
I5—Bi1—I7—Bi3	−86.395 (18)	C15—C14—C24—C23	180.0 (9)
I4—Bi2—I9—Bi3^i	−86.046 (19)	O2—C14—C24—C20	−174.0 (9)
I5—Bi2—I9—Bi3^i	179.143 (17)	C15—C14—C24—C20	4.4 (9)
I10—Bi2—I9—Bi3^i	7.089 (17)	C2—C6—N1—C5	1.2 (12)
I10^i—Bi2—I9—Bi3^i	93.164 (16)	C7—C6—N1—C5	−179.4 (8)
I4—Bi2—I10—Bi3^i	86.729 (18)	C2—C6—N1—C12	−177.4 (8)
I9—Bi2—I10—Bi3^i	−6.724 (16)	C7—C6—N1—C12	2.0 (14)
I6—Bi2—I10—Bi3^i	−179.917 (14)	C4—C5—N1—C6	−0.8 (14)
I10^i—Bi2—I10—Bi3^i	−96.863 (15)	C4—C5—N1—C12	177.8 (9)
I4—Bi2—I10—Bi2^i	−176.407 (19)	C13—C12—N1—C6	−96.0 (10)
I9—Bi2—I10—Bi2^i	90.140 (16)	C13—C12—N1—C5	85.4 (10)
I6—Bi2—I10—Bi2^i	−83.053 (14)	C11—C7—N2—C8	−0.7 (13)
I10^i—Bi2—I10—Bi2^i	0.001 (2)	C6—C7—N2—C8	178.3 (8)
O1—C1—C2—C3	0.1 (17)	C9—C8—N2—C7	0.1 (13)
C11—C1—C2—C3	179.9 (9)	C15—C19—N3—C18	−2.6 (11)
O1—C1—C2—C6	−178.9 (10)	C20—C19—N3—C18	175.4 (8)
C11—C1—C2—C6	0.9 (10)	C15—C19—N3—C25	176.8 (8)
C6—C2—C3—C4	0.7 (13)	C20—C19—N3—C25	−5.2 (13)
C1—C2—C3—C4	−178.1 (9)	C17—C18—N3—C19	0.0 (12)
C2—C3—C4—C5	−0.4 (14)	C17—C18—N3—C25	−179.4 (8)
C3—C4—C5—N1	0.4 (15)	C26—C25—N3—C19	−168.6 (8)
C3—C2—C6—N1	−1.1 (13)	C26—C25—N3—C18	10.8 (12)
C1—C2—C6—N1	177.9 (8)	C24—C20—N4—C21	1.7 (13)
C3—C2—C6—C7	179.4 (7)	C19—C20—N4—C21	−179.8 (8)
C1—C2—C6—C7	−1.6 (10)	C22—C21—N4—C20	−2.0 (14)

Symmetry code: (i) −x+1, −y+1, −z+1.