Crystal structure of (C9H17N2)3[Bi2I9]

James, Z.; Cai, Y.; Vaqueiro, P.

doi:10.1107/S2056989021007799

Crystal structure of (C₉H₁₇N₂)₃[Bi₂I₉]

The crystal structure of (C₉H₇N₂)₃Bi₂I₉ contains dinuclear [Bi₂I₉]³⁻ anions, formed by two face-sharing octahedra, and protonated 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) cations.

Keywords: crystal structure; iodobismuthate; photovoltaic materials.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021007799/jq2007sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021007799/jq2007Isup3.hkl Contains datablock I
	Chemdraw file https://doi.org/10.1107/S2056989021007799/jq2007Isup4.cdx Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S2056989021007799/jq2007sup5.pdf Fingerprint plots, powder diffraction and TGA data.

CCDC reference: 2100182

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.011 Å
Disorder in main residue
R factor = 0.036
wR factor = 0.086
Data-to-parameter ratio = 27.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT972_ALERT_2_B Check Calcd Resid. Dens.  1.15A   From Bi1            -2.65 eA-3

Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01114 Ang.
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N30      --H30      .     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H41      ..I8       .       3.21 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        153 Report
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.08A   From Bi1             2.32 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.62A   From I5              2.27 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.81A   From I10             2.07 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.51A   From I9              2.01 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.15A   From Bi1             1.99 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.17A   From Bi3             1.89 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.22A   From Bi1             1.86 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.63A   From I4              1.83 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.68A   From Bi3             1.78 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.95A   From Bi3             1.65 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.71A   From Bi1             1.62 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.78A   From Bi1             1.62 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.15A   From I9              1.61 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.05A   From Bi3             1.60 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.85A   From I4              1.59 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.12A   From Bi3             1.59 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.92A   From I11             1.56 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.43A   From I9              1.55 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.23A   From I5              1.54 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.72A   From Bi1             1.53 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.65A   From Bi1             1.52 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.13A   From Bi3            -2.19 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.16A   From Bi1            -1.95 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.75A   From Bi1            -1.93 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.63A   From Bi3            -1.79 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.78A   From Bi3            -1.72 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  0.94A   From Bi1            -1.65 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.23A   From Bi3            -1.61 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.79A   From I9             -1.61 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.78A   From Bi1            -1.58 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  0.88A   From Bi1            -1.55 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H25B             -0.33 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H31B             -0.46 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H42A             -0.45 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H43B             -0.57 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H37D             -0.32 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         22 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         22 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT042_ALERT_1_G Calc. and Reported Moiety Formula Strings Differ     Please Check
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Bi1      --I2       .        5.5 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Bi1      --I4       .       13.5 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Bi1      --I5       .        6.5 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Bi3      --I2       .        8.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Bi3      --I5       .       11.5 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  4  )       100% Note
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  5  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  4  )      15.99 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  5  )      12.01 Check
PLAT794_ALERT_5_G Tentative Bond Valency for Bi1       (III)     .       3.04 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Bi3       (III)     .       3.05 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        543 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        472 Note

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

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

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ATOMS (Dowty, 2020) and ORIGIN (Edwards, 2002).

Tris(2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium) tri-µ₂-iodido-bis[triiodidobismuth(III)] top

Crystal data top

(C₉H₁₇N₂)₃[Bi₂I₉]	F(000) = 3592
M_r = 2019.79	D_x = 2.840 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.2590 (9) Å	Cell parameters from 25746 reflections
b = 12.5734 (3) Å	θ = 2–33°
c = 21.6767 (9) Å	µ = 13.35 mm⁻¹
β = 115.861 (5)°	T = 100 K
V = 4723.4 (4) Å³	Plate, red
Z = 4	0.31 × 0.23 × 0.07 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	11096 reflections with I > 2σ(I)
ω scans	R_int = 0.034
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	θ_max = 30.5°, θ_min = 2.4°
T_min = 0.23, T_max = 1.00	h = −27→27
38319 measured reflections	k = −13→17
13780 independent reflections	l = −30→29

Refinement top

Refinement on F²	543 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0423P)² + 1.9329P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
13780 reflections	Δρ_max = 2.22 e Å⁻³
497 parameters	Δρ_min = −2.57 e Å⁻³

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)
Bi1	0.18727 (2)	0.75290 (2)	0.16730 (2)	0.01478 (5)
Bi3	0.31503 (2)	0.48511 (2)	0.25029 (2)	0.01518 (5)
I2	0.18622 (2)	0.60345 (3)	0.28735 (2)	0.01778 (8)
I4	0.19072 (2)	0.52615 (3)	0.09942 (2)	0.01934 (8)
I5	0.37010 (2)	0.72314 (3)	0.24092 (2)	0.02467 (9)
I6	0.24567 (3)	0.27208 (3)	0.24502 (2)	0.02245 (9)
I7	0.42044 (3)	0.48954 (3)	0.40035 (2)	0.02341 (9)
I8	0.42451 (3)	0.39855 (3)	0.20120 (2)	0.02961 (10)
I9	0.01394 (2)	0.74983 (3)	0.10767 (2)	0.01875 (8)
I10	0.17891 (3)	0.84909 (3)	0.03995 (2)	0.02861 (10)
I11	0.21740 (3)	0.95712 (3)	0.24184 (2)	0.02482 (9)
N12	−0.0295 (3)	0.7605 (4)	0.3236 (2)	0.0195 (10)
N19	−0.0307 (4)	0.7271 (4)	0.4272 (3)	0.0258 (12)
H19	−0.027161	0.752892	0.466231	0.031*
N23	0.4254 (4)	0.8196 (5)	0.5457 (3)	0.0360 (15)
N30	0.3585 (4)	0.8010 (5)	0.4269 (3)	0.0396 (15)
H30	0.359982	0.793472	0.387180	0.048*
C13	−0.0306 (4)	0.8352 (5)	0.2708 (3)	0.0229 (13)
H13A	−0.066990	0.893757	0.265999	0.028*
H13B	−0.049722	0.797679	0.226308	0.028*
C14	0.0479 (4)	0.8816 (5)	0.2876 (3)	0.0270 (15)
H14A	0.048509	0.907961	0.244777	0.032*
H14B	0.087103	0.824650	0.306148	0.032*
C15	0.0701 (5)	0.9724 (5)	0.3392 (3)	0.0278 (15)
H15A	0.033195	1.031594	0.319000	0.033*
H15B	0.121944	0.998640	0.347472	0.033*
C16	0.0714 (4)	0.9420 (5)	0.4083 (3)	0.0221 (13)
H16A	0.108721	0.883316	0.428703	0.027*
H16B	0.089943	1.003738	0.439604	0.027*
C17	−0.0061 (4)	0.9077 (5)	0.4035 (3)	0.0238 (13)
H17A	−0.006610	0.918916	0.448522	0.029*
H17B	−0.046909	0.952911	0.369487	0.029*
C18	−0.0238 (4)	0.7931 (5)	0.3832 (3)	0.0183 (11)
C20	−0.0438 (5)	0.6139 (5)	0.4146 (3)	0.0389 (19)
H20A	−0.099868	0.598977	0.392050	0.047*
H20B	−0.020771	0.574505	0.458548	0.047*
C21	−0.0072 (5)	0.5788 (5)	0.3692 (4)	0.0374 (18)
H21A	0.049581	0.584182	0.394607	0.045*
H21B	−0.020549	0.503466	0.355954	0.045*
C22	−0.0347 (5)	0.6463 (5)	0.3062 (3)	0.0283 (15)
H22A	−0.003083	0.631452	0.281397	0.034*
H22B	−0.088950	0.627970	0.275421	0.034*
C24	0.4962 (5)	0.8075 (6)	0.6123 (3)	0.0354 (18)
H24A	0.518750	0.736198	0.613821	0.043*
H24B	0.481188	0.811679	0.650508	0.043*
C25	0.5580 (5)	0.8926 (6)	0.6230 (4)	0.0354 (17)
H25A	0.532320	0.962602	0.608853	0.043*
H25B	0.593503	0.896773	0.672436	0.043*
C26	0.6046 (5)	0.8709 (6)	0.5832 (4)	0.0383 (18)
H26A	0.633464	0.803665	0.600267	0.046*
H26B	0.643041	0.928566	0.593145	0.046*
C27	0.5574 (5)	0.8623 (5)	0.5048 (4)	0.0324 (16)
H27A	0.529891	0.930270	0.487396	0.039*
H27B	0.593515	0.852186	0.483876	0.039*
C28	0.4989 (5)	0.7723 (5)	0.4815 (4)	0.0325 (17)
H28A	0.486300	0.754439	0.433334	0.039*
H28B	0.522400	0.708599	0.509803	0.039*
C29	0.4259 (4)	0.7989 (5)	0.4868 (3)	0.0244 (14)
C31	0.2843 (5)	0.8157 (7)	0.4294 (4)	0.0391 (18)
H31A	0.265602	0.746710	0.438399	0.047*
H31B	0.245533	0.843192	0.384877	0.047*
C32	0.2947 (5)	0.8938 (6)	0.4860 (4)	0.0427 (19)
H32A	0.306527	0.965247	0.473852	0.051*
H32B	0.246359	0.898744	0.491447	0.051*
C33	0.3583 (5)	0.8581 (6)	0.5509 (4)	0.0339 (16)
H33A	0.373768	0.918258	0.583628	0.041*
H33B	0.338628	0.800906	0.570454	0.041*
N34	0.7076 (14)	0.569 (2)	0.4694 (6)	0.018 (2)	0.571 (13)
C35	0.7601 (11)	0.5636 (16)	0.5432 (7)	0.018 (3)	0.571 (13)
H35A	0.813909	0.558906	0.549092	0.022*	0.571 (13)
H35B	0.748948	0.498240	0.562769	0.022*	0.571 (13)
C36	0.7528 (11)	0.6591 (18)	0.5828 (10)	0.025 (3)	0.571 (13)
H36A	0.774972	0.639947	0.631953	0.030*	0.571 (13)
H36B	0.697209	0.673716	0.567634	0.030*	0.571 (13)
C37	0.7915 (15)	0.7619 (14)	0.5756 (10)	0.024 (3)	0.571 (13)
H37A	0.777857	0.819481	0.599494	0.029*	0.571 (13)
H37B	0.848090	0.751928	0.599731	0.029*	0.571 (13)
C38	0.7712 (11)	0.7984 (14)	0.5031 (10)	0.027 (3)	0.571 (13)
H38A	0.802108	0.862452	0.505442	0.032*	0.571 (13)
H38B	0.716141	0.819577	0.481252	0.032*	0.571 (13)
C39	0.7844 (9)	0.7154 (13)	0.4570 (8)	0.024 (3)	0.571 (13)
H39A	0.788929	0.752081	0.418453	0.028*	0.571 (13)
H39B	0.833494	0.677330	0.483789	0.028*	0.571 (13)
C40	0.7199 (12)	0.6369 (17)	0.4291 (7)	0.024 (4)	0.571 (13)
N41	0.6722 (8)	0.6439 (10)	0.3640 (6)	0.031 (3)	0.571 (13)
H41	0.682573	0.690516	0.338939	0.037*	0.571 (13)
C42	0.6022 (8)	0.5786 (10)	0.3302 (6)	0.031 (3)	0.571 (13)
H42A	0.590982	0.566712	0.281668	0.037*	0.571 (13)
H42B	0.557524	0.615825	0.331593	0.037*	0.571 (13)
C43	0.6149 (8)	0.4726 (8)	0.3674 (5)	0.027 (2)	0.571 (13)
H43A	0.565860	0.432290	0.349771	0.033*	0.571 (13)
H43B	0.653090	0.429953	0.358891	0.033*	0.571 (13)
C44	0.6436 (8)	0.4913 (12)	0.4427 (6)	0.020 (3)	0.571 (13)
H44A	0.600588	0.517838	0.451858	0.024*	0.571 (13)
H44B	0.661310	0.422934	0.467339	0.024*	0.571 (13)
N34A	0.7037 (19)	0.565 (3)	0.4637 (9)	0.020 (3)	0.429 (13)
C35A	0.7431 (15)	0.557 (2)	0.5392 (9)	0.018 (4)	0.429 (13)
H35C	0.798368	0.541270	0.553819	0.021*	0.429 (13)
H35D	0.720485	0.498255	0.554487	0.021*	0.429 (13)
C36A	0.7363 (15)	0.660 (2)	0.5737 (12)	0.020 (3)	0.429 (13)
H36C	0.741545	0.643507	0.620154	0.024*	0.429 (13)
H36D	0.684452	0.691150	0.546985	0.024*	0.429 (13)
C37A	0.7984 (19)	0.7428 (19)	0.5793 (12)	0.022 (4)	0.429 (13)
H37C	0.795358	0.804298	0.606510	0.026*	0.429 (13)
H37D	0.850144	0.710386	0.603988	0.026*	0.429 (13)
C38A	0.7887 (14)	0.7819 (16)	0.5091 (12)	0.022 (4)	0.429 (13)
H38C	0.826561	0.839271	0.515949	0.026*	0.429 (13)
H38D	0.736426	0.812666	0.484167	0.026*	0.429 (13)
C39A	0.7998 (11)	0.6933 (16)	0.4645 (11)	0.019 (3)	0.429 (13)
H39C	0.813384	0.726348	0.429756	0.022*	0.429 (13)
H39D	0.843318	0.647143	0.493943	0.022*	0.429 (13)
C40A	0.7293 (14)	0.626 (2)	0.4290 (8)	0.017 (3)	0.429 (13)
N41A	0.6957 (8)	0.6272 (12)	0.3614 (8)	0.018 (3)	0.429 (13)
H41A	0.717128	0.664894	0.340134	0.022*	0.429 (13)
C42A	0.6248 (11)	0.5690 (16)	0.3198 (8)	0.029 (3)	0.429 (13)
H42C	0.637673	0.498814	0.306758	0.035*	0.429 (13)
H42D	0.593866	0.609199	0.277302	0.035*	0.429 (13)
C43A	0.5791 (9)	0.5543 (12)	0.3608 (7)	0.027 (3)	0.429 (13)
H43C	0.558783	0.623766	0.366852	0.032*	0.429 (13)
H43D	0.534828	0.506463	0.335744	0.032*	0.429 (13)
C44A	0.6295 (13)	0.5075 (19)	0.4294 (8)	0.026 (4)	0.429 (13)
H44C	0.602112	0.510448	0.458819	0.031*	0.429 (13)
H44D	0.639682	0.431902	0.423618	0.031*	0.429 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Bi1	0.01519 (11)	0.01399 (10)	0.01444 (10)	0.00064 (8)	0.00580 (9)	0.00318 (7)
Bi3	0.01585 (11)	0.01421 (10)	0.01379 (10)	0.00126 (8)	0.00490 (9)	−0.00033 (7)
I2	0.0225 (2)	0.01701 (17)	0.01585 (16)	0.00304 (14)	0.01026 (16)	0.00337 (12)
I4	0.0213 (2)	0.02260 (18)	0.01239 (16)	0.00069 (15)	0.00570 (16)	−0.00100 (13)
I5	0.0158 (2)	0.02024 (18)	0.0350 (2)	−0.00150 (15)	0.00837 (18)	0.00284 (15)
I6	0.0314 (2)	0.01434 (17)	0.01965 (18)	−0.00229 (15)	0.00928 (18)	−0.00232 (13)
I7	0.0242 (2)	0.02374 (19)	0.01498 (17)	0.00049 (16)	0.00181 (17)	0.00064 (14)
I8	0.0222 (2)	0.0374 (2)	0.0300 (2)	0.00495 (18)	0.01215 (19)	−0.00864 (17)
I9	0.01549 (19)	0.02433 (18)	0.01576 (17)	0.00086 (15)	0.00617 (16)	0.00014 (13)
I10	0.0275 (2)	0.0353 (2)	0.0234 (2)	−0.00061 (18)	0.01148 (19)	0.01407 (16)
I11	0.0246 (2)	0.01504 (17)	0.0310 (2)	0.00004 (16)	0.00855 (19)	−0.00205 (14)
N12	0.021 (3)	0.022 (2)	0.015 (2)	−0.003 (2)	0.008 (2)	−0.0051 (18)
N19	0.033 (3)	0.026 (3)	0.015 (2)	−0.010 (2)	0.007 (2)	−0.0008 (19)
N23	0.047 (4)	0.038 (3)	0.028 (3)	0.002 (3)	0.020 (3)	−0.001 (2)
N30	0.041 (4)	0.054 (4)	0.023 (3)	0.005 (3)	0.014 (3)	−0.008 (3)
C13	0.029 (4)	0.025 (3)	0.014 (3)	−0.004 (3)	0.010 (3)	−0.002 (2)
C14	0.037 (4)	0.027 (3)	0.021 (3)	−0.012 (3)	0.016 (3)	−0.008 (2)
C15	0.037 (4)	0.022 (3)	0.024 (3)	−0.006 (3)	0.013 (3)	−0.001 (2)
C16	0.029 (4)	0.019 (3)	0.010 (3)	−0.001 (3)	0.001 (3)	−0.003 (2)
C17	0.031 (4)	0.026 (3)	0.019 (3)	0.003 (3)	0.016 (3)	−0.004 (2)
C18	0.012 (3)	0.024 (3)	0.014 (3)	0.001 (2)	0.001 (2)	0.001 (2)
C20	0.055 (6)	0.032 (4)	0.019 (3)	−0.019 (4)	0.006 (4)	0.000 (3)
C21	0.049 (5)	0.016 (3)	0.034 (4)	−0.002 (3)	0.005 (4)	−0.003 (3)
C22	0.039 (4)	0.021 (3)	0.022 (3)	−0.004 (3)	0.011 (3)	−0.007 (2)
C24	0.047 (5)	0.038 (4)	0.022 (3)	0.017 (3)	0.016 (4)	0.011 (3)
C25	0.036 (5)	0.044 (4)	0.026 (3)	0.008 (3)	0.013 (3)	0.002 (3)
C26	0.039 (5)	0.041 (4)	0.038 (4)	0.017 (4)	0.019 (4)	0.006 (3)
C27	0.037 (5)	0.031 (3)	0.038 (4)	0.014 (3)	0.025 (4)	0.008 (3)
C28	0.048 (5)	0.028 (3)	0.026 (3)	0.017 (3)	0.019 (4)	0.007 (3)
C29	0.034 (4)	0.019 (3)	0.020 (3)	0.009 (3)	0.011 (3)	0.003 (2)
C31	0.031 (4)	0.059 (5)	0.027 (4)	−0.010 (4)	0.012 (3)	−0.010 (3)
C32	0.035 (5)	0.057 (5)	0.041 (4)	0.000 (4)	0.021 (4)	−0.013 (4)
C33	0.040 (5)	0.038 (4)	0.028 (4)	0.003 (3)	0.019 (4)	−0.003 (3)
N34	0.024 (5)	0.019 (4)	0.014 (4)	0.002 (4)	0.011 (4)	0.002 (3)
C35	0.021 (7)	0.017 (5)	0.018 (4)	0.001 (5)	0.010 (4)	0.005 (4)
C36	0.028 (7)	0.025 (5)	0.021 (5)	−0.001 (5)	0.010 (5)	−0.004 (4)
C37	0.024 (6)	0.022 (6)	0.027 (5)	0.002 (5)	0.011 (5)	−0.004 (5)
C38	0.025 (7)	0.022 (6)	0.030 (5)	−0.001 (5)	0.010 (5)	0.003 (4)
C39	0.026 (6)	0.028 (6)	0.016 (5)	−0.002 (5)	0.008 (5)	0.009 (4)
C40	0.026 (6)	0.027 (6)	0.017 (4)	0.001 (5)	0.009 (4)	0.007 (4)
N41	0.028 (6)	0.038 (6)	0.020 (4)	−0.010 (5)	0.004 (4)	0.010 (4)
C42	0.028 (6)	0.034 (5)	0.015 (5)	−0.002 (5)	−0.004 (4)	0.007 (4)
C43	0.028 (5)	0.029 (5)	0.019 (4)	0.002 (4)	0.004 (4)	0.004 (3)
C44	0.018 (5)	0.022 (5)	0.017 (4)	0.004 (4)	0.005 (4)	0.003 (4)
N34A	0.025 (5)	0.018 (6)	0.014 (4)	−0.001 (5)	0.007 (4)	0.003 (4)
C35A	0.020 (8)	0.018 (6)	0.015 (4)	−0.004 (6)	0.007 (5)	−0.003 (4)
C36A	0.023 (7)	0.024 (5)	0.016 (6)	−0.005 (6)	0.012 (6)	−0.003 (5)
C37A	0.027 (7)	0.017 (7)	0.024 (5)	−0.005 (6)	0.013 (5)	−0.007 (5)
C38A	0.022 (8)	0.013 (6)	0.028 (6)	0.004 (6)	0.009 (6)	0.005 (5)
C39A	0.020 (7)	0.017 (7)	0.020 (6)	0.001 (5)	0.009 (5)	0.005 (5)
C40A	0.018 (6)	0.018 (6)	0.017 (4)	0.006 (5)	0.009 (4)	0.002 (4)
N41A	0.018 (6)	0.022 (5)	0.015 (4)	0.003 (5)	0.007 (4)	0.000 (4)
C42A	0.028 (7)	0.043 (7)	0.014 (5)	−0.006 (5)	0.007 (4)	−0.004 (5)
C43A	0.023 (6)	0.036 (6)	0.019 (5)	−0.005 (5)	0.007 (4)	0.003 (5)
C44A	0.030 (7)	0.022 (7)	0.020 (5)	−0.007 (6)	0.005 (5)	0.002 (5)

Geometric parameters (Å, º) top

Bi1—I10	2.9532 (4)	C31—H31B	0.9900
Bi1—I11	2.9534 (4)	C32—C33	1.476 (11)
Bi1—I9	3.0085 (5)	C32—H32A	0.9900
Bi1—I5	3.1911 (5)	C32—H32B	0.9900
Bi1—I2	3.2169 (4)	C33—H33A	0.9900
Bi1—I4	3.2224 (4)	C33—H33B	0.9900
Bi3—I8	2.9530 (5)	N34—C40	1.318 (11)
Bi3—I6	2.9730 (4)	N34—C35	1.475 (12)
Bi3—I7	2.9908 (5)	N34—C44	1.475 (13)
Bi3—I4	3.1405 (5)	C35—C36	1.516 (12)
Bi3—I5	3.2111 (4)	C35—H35A	0.9900
Bi3—I2	3.2788 (4)	C35—H35B	0.9900
N12—C18	1.313 (7)	C36—C37	1.533 (13)
N12—C13	1.473 (7)	C36—H36A	0.9900
N12—C22	1.477 (7)	C36—H36B	0.9900
N19—C18	1.314 (7)	C37—C38	1.516 (13)
N19—C20	1.451 (8)	C37—H37A	0.9900
N19—H19	0.8800	C37—H37B	0.9900
N23—C29	1.308 (7)	C38—C39	1.543 (13)
N23—C33	1.430 (10)	C38—H38A	0.9900
N23—C24	1.500 (10)	C38—H38B	0.9900
N30—C29	1.379 (9)	C39—C40	1.493 (13)
N30—C31	1.465 (10)	C39—H39A	0.9900
N30—H30	0.8800	C39—H39B	0.9900
C13—C14	1.510 (9)	C40—N41	1.308 (12)
C13—H13A	0.9900	N41—C42	1.472 (14)
C13—H13B	0.9900	N41—H41	0.8800
C14—C15	1.523 (8)	C42—C43	1.521 (14)
C14—H14A	0.9900	C42—H42A	0.9900
C14—H14B	0.9900	C42—H42B	0.9900
C15—C16	1.536 (8)	C43—C44	1.497 (16)
C15—H15A	0.9900	C43—H43A	0.9900
C15—H15B	0.9900	C43—H43B	0.9900
C16—C17	1.512 (9)	C44—H44A	0.9900
C16—H16A	0.9900	C44—H44B	0.9900
C16—H16B	0.9900	N34A—C40A	1.319 (13)
C17—C18	1.502 (8)	N34A—C35A	1.476 (13)
C17—H17A	0.9900	N34A—C44A	1.477 (15)
C17—H17B	0.9900	C35A—C36A	1.525 (14)
C20—C21	1.505 (11)	C35A—H35C	0.9900
C20—H20A	0.9900	C35A—H35D	0.9900
C20—H20B	0.9900	C36A—C37A	1.549 (16)
C21—C22	1.495 (9)	C36A—H36C	0.9900
C21—H21A	0.9900	C36A—H36D	0.9900
C21—H21B	0.9900	C37A—C38A	1.530 (14)
C22—H22A	0.9900	C37A—H37C	0.9900
C22—H22B	0.9900	C37A—H37D	0.9900
C24—C25	1.541 (11)	C38A—C39A	1.551 (15)
C24—H24A	0.9900	C38A—H38C	0.9900
C24—H24B	0.9900	C38A—H38D	0.9900
C25—C26	1.517 (10)	C39A—C40A	1.492 (14)
C25—H25A	0.9900	C39A—H39C	0.9900
C25—H25B	0.9900	C39A—H39D	0.9900
C26—C27	1.542 (11)	C40A—N41A	1.317 (13)
C26—H26A	0.9900	N41A—C42A	1.462 (15)
C26—H26B	0.9900	N41A—H41A	0.8800
C27—C28	1.519 (11)	C42A—C43A	1.510 (16)
C27—H27A	0.9900	C42A—H42C	0.9900
C27—H27B	0.9900	C42A—H42D	0.9900
C28—C29	1.497 (10)	C43A—C44A	1.497 (18)
C28—H28A	0.9900	C43A—H43C	0.9900
C28—H28B	0.9900	C43A—H43D	0.9900
C31—C32	1.515 (10)	C44A—H44C	0.9900
C31—H31A	0.9900	C44A—H44D	0.9900

I10—Bi1—I11	94.180 (13)	C32—C31—H31A	109.9
I10—Bi1—I9	90.328 (14)	N30—C31—H31B	109.9
I11—Bi1—I9	99.358 (13)	C32—C31—H31B	109.9
I10—Bi1—I5	96.536 (14)	H31A—C31—H31B	108.3
I11—Bi1—I5	85.283 (13)	C33—C32—C31	109.6 (7)
I9—Bi1—I5	171.439 (12)	C33—C32—H32A	109.7
I10—Bi1—I2	168.049 (13)	C31—C32—H32A	109.7
I11—Bi1—I2	97.725 (12)	C33—C32—H32B	109.7
I9—Bi1—I2	86.722 (12)	C31—C32—H32B	109.7
I5—Bi1—I2	85.519 (12)	H32A—C32—H32B	108.2
I10—Bi1—I4	86.507 (12)	N23—C33—C32	115.5 (6)
I11—Bi1—I4	168.754 (14)	N23—C33—H33A	108.4
I9—Bi1—I4	91.859 (12)	C32—C33—H33A	108.4
I5—Bi1—I4	83.488 (12)	N23—C33—H33B	108.4
I2—Bi1—I4	82.022 (10)	C32—C33—H33B	108.4
I8—Bi3—I6	91.922 (13)	H33A—C33—H33B	107.5
I8—Bi3—I7	98.404 (15)	C40—N34—C35	120.7 (11)
I6—Bi3—I7	97.988 (12)	C40—N34—C44	122.0 (10)
I8—Bi3—I4	91.439 (13)	C35—N34—C44	117.2 (10)
I6—Bi3—I4	88.991 (12)	N34—C35—C36	113.0 (13)
I7—Bi3—I4	167.695 (12)	N34—C35—H35A	109.0
I8—Bi3—I5	90.760 (13)	C36—C35—H35A	109.0
I6—Bi3—I5	173.004 (14)	N34—C35—H35B	109.0
I7—Bi3—I5	88.005 (12)	C36—C35—H35B	109.0
I4—Bi3—I5	84.482 (12)	H35A—C35—H35B	107.8
I8—Bi3—I2	172.288 (13)	C35—C36—C37	116.2 (12)
I6—Bi3—I2	92.465 (12)	C35—C36—H36A	108.2
I7—Bi3—I2	87.263 (12)	C37—C36—H36A	108.2
I4—Bi3—I2	82.301 (11)	C35—C36—H36B	108.2
I5—Bi3—I2	84.183 (11)	C37—C36—H36B	108.2
Bi1—I2—Bi3	78.144 (9)	H36A—C36—H36B	107.4
Bi3—I4—Bi1	80.095 (10)	C38—C37—C36	116.3 (13)
Bi1—I5—Bi3	79.516 (11)	C38—C37—H37A	108.2
C18—N12—C13	122.1 (5)	C36—C37—H37A	108.2
C18—N12—C22	121.5 (5)	C38—C37—H37B	108.2
C13—N12—C22	116.4 (4)	C36—C37—H37B	108.2
C18—N19—C20	123.2 (5)	H37A—C37—H37B	107.4
C18—N19—H19	118.4	C37—C38—C39	115.2 (12)
C20—N19—H19	118.4	C37—C38—H38A	108.5
C29—N23—C33	122.4 (7)	C39—C38—H38A	108.5
C29—N23—C24	121.9 (6)	C37—C38—H38B	108.5
C33—N23—C24	115.6 (5)	C39—C38—H38B	108.5
C29—N30—C31	120.1 (6)	H38A—C38—H38B	107.5
C29—N30—H30	119.9	C40—C39—C38	111.4 (12)
C31—N30—H30	119.9	C40—C39—H39A	109.3
N12—C13—C14	112.7 (5)	C38—C39—H39A	109.3
N12—C13—H13A	109.0	C40—C39—H39B	109.3
C14—C13—H13A	109.0	C38—C39—H39B	109.3
N12—C13—H13B	109.0	H39A—C39—H39B	108.0
C14—C13—H13B	109.0	N41—C40—N34	120.9 (11)
H13A—C13—H13B	107.8	N41—C40—C39	117.4 (11)
C13—C14—C15	113.4 (5)	N34—C40—C39	121.4 (11)
C13—C14—H14A	108.9	C40—N41—C42	124.0 (11)
C15—C14—H14A	108.9	C40—N41—H41	118.0
C13—C14—H14B	108.9	C42—N41—H41	118.0
C15—C14—H14B	108.9	N41—C42—C43	108.9 (10)
H14A—C14—H14B	107.7	N41—C42—H42A	109.9
C14—C15—C16	114.2 (5)	C43—C42—H42A	109.9
C14—C15—H15A	108.7	N41—C42—H42B	109.9
C16—C15—H15A	108.7	C43—C42—H42B	109.9
C14—C15—H15B	108.7	H42A—C42—H42B	108.3
C16—C15—H15B	108.7	C44—C43—C42	109.7 (10)
H15A—C15—H15B	107.6	C44—C43—H43A	109.7
C17—C16—C15	114.2 (5)	C42—C43—H43A	109.7
C17—C16—H16A	108.7	C44—C43—H43B	109.7
C15—C16—H16A	108.7	C42—C43—H43B	109.7
C17—C16—H16B	108.7	H43A—C43—H43B	108.2
C15—C16—H16B	108.7	N34—C44—C43	112.3 (10)
H16A—C16—H16B	107.6	N34—C44—H44A	109.2
C18—C17—C16	112.6 (5)	C43—C44—H44A	109.2
C18—C17—H17A	109.1	N34—C44—H44B	109.2
C16—C17—H17A	109.1	C43—C44—H44B	109.2
C18—C17—H17B	109.1	H44A—C44—H44B	107.9
C16—C17—H17B	109.1	C40A—N34A—C35A	121.9 (14)
H17A—C17—H17B	107.8	C40A—N34A—C44A	121.3 (13)
N12—C18—N19	121.7 (5)	C35A—N34A—C44A	116.4 (14)
N12—C18—C17	120.0 (5)	N34A—C35A—C36A	112.3 (17)
N19—C18—C17	118.3 (5)	N34A—C35A—H35C	109.1
N19—C20—C21	108.6 (6)	C36A—C35A—H35C	109.1
N19—C20—H20A	110.0	N34A—C35A—H35D	109.1
C21—C20—H20A	110.0	C36A—C35A—H35D	109.1
N19—C20—H20B	110.0	H35C—C35A—H35D	107.9
C21—C20—H20B	110.0	C35A—C36A—C37A	112.2 (16)
H20A—C20—H20B	108.4	C35A—C36A—H36C	109.2
C22—C21—C20	110.6 (6)	C37A—C36A—H36C	109.2
C22—C21—H21A	109.5	C35A—C36A—H36D	109.2
C20—C21—H21A	109.5	C37A—C36A—H36D	109.2
C22—C21—H21B	109.5	H36C—C36A—H36D	107.9
C20—C21—H21B	109.5	C38A—C37A—C36A	112.5 (17)
H21A—C21—H21B	108.1	C38A—C37A—H37C	109.1
N12—C22—C21	111.1 (5)	C36A—C37A—H37C	109.1
N12—C22—H22A	109.4	C38A—C37A—H37D	109.1
C21—C22—H22A	109.4	C36A—C37A—H37D	109.1
N12—C22—H22B	109.4	H37C—C37A—H37D	107.8
C21—C22—H22B	109.4	C37A—C38A—C39A	113.5 (14)
H22A—C22—H22B	108.0	C37A—C38A—H38C	108.9
N23—C24—C25	113.1 (5)	C39A—C38A—H38C	108.9
N23—C24—H24A	109.0	C37A—C38A—H38D	108.9
C25—C24—H24A	109.0	C39A—C38A—H38D	108.9
N23—C24—H24B	109.0	H38C—C38A—H38D	107.7
C25—C24—H24B	109.0	C40A—C39A—C38A	112.6 (15)
H24A—C24—H24B	107.8	C40A—C39A—H39C	109.1
C26—C25—C24	113.6 (6)	C38A—C39A—H39C	109.1
C26—C25—H25A	108.9	C40A—C39A—H39D	109.1
C24—C25—H25A	108.9	C38A—C39A—H39D	109.1
C26—C25—H25B	108.9	H39C—C39A—H39D	107.8
C24—C25—H25B	108.9	N41A—C40A—N34A	120.9 (13)
H25A—C25—H25B	107.7	N41A—C40A—C39A	117.7 (14)
C25—C26—C27	115.3 (7)	N34A—C40A—C39A	121.3 (13)
C25—C26—H26A	108.4	C40A—N41A—C42A	123.8 (13)
C27—C26—H26A	108.4	C40A—N41A—H41A	118.1
C25—C26—H26B	108.4	C42A—N41A—H41A	118.1
C27—C26—H26B	108.4	N41A—C42A—C43A	108.9 (12)
H26A—C26—H26B	107.5	N41A—C42A—H42C	109.9
C28—C27—C26	114.4 (6)	C43A—C42A—H42C	109.9
C28—C27—H27A	108.7	N41A—C42A—H42D	109.9
C26—C27—H27A	108.7	C43A—C42A—H42D	109.9
C28—C27—H27B	108.7	H42C—C42A—H42D	108.3
C26—C27—H27B	108.7	C44A—C43A—C42A	110.0 (15)
H27A—C27—H27B	107.6	C44A—C43A—H43C	109.7
C29—C28—C27	113.2 (5)	C42A—C43A—H43C	109.7
C29—C28—H28A	108.9	C44A—C43A—H43D	109.7
C27—C28—H28A	108.9	C42A—C43A—H43D	109.7
C29—C28—H28B	108.9	H43C—C43A—H43D	108.2
C27—C28—H28B	108.9	N34A—C44A—C43A	112.0 (14)
H28A—C28—H28B	107.7	N34A—C44A—H44C	109.2
N23—C29—N30	120.6 (6)	C43A—C44A—H44C	109.2
N23—C29—C28	121.7 (6)	N34A—C44A—H44D	109.2
N30—C29—C28	117.6 (5)	C43A—C44A—H44D	109.2
N30—C31—C32	108.9 (6)	H44C—C44A—H44D	107.9
N30—C31—H31A	109.9

C18—N12—C13—C14	74.6 (7)	C40—N34—C35—C36	71 (3)
C22—N12—C13—C14	−105.1 (6)	C44—N34—C35—C36	−111 (2)
N12—C13—C14—C15	−79.8 (7)	N34—C35—C36—C37	−77.1 (19)
C13—C14—C15—C16	58.5 (8)	C35—C36—C37—C38	52 (2)
C14—C15—C16—C17	−62.5 (8)	C36—C37—C38—C39	−55 (2)
C15—C16—C17—C18	82.5 (6)	C37—C38—C39—C40	80.1 (16)
C13—N12—C18—N19	173.0 (6)	C35—N34—C40—N41	−178 (2)
C22—N12—C18—N19	−7.4 (10)	C44—N34—C40—N41	5 (5)
C13—N12—C18—C17	−9.3 (9)	C35—N34—C40—C39	−3 (4)
C22—N12—C18—C17	170.3 (6)	C44—N34—C40—C39	179 (2)
C20—N19—C18—N12	1.0 (11)	C38—C39—C40—N41	108 (2)
C20—N19—C18—C17	−176.7 (7)	C38—C39—C40—N34	−67 (3)
C16—C17—C18—N12	−61.7 (8)	N34—C40—N41—C42	0 (4)
C16—C17—C18—N19	116.1 (6)	C39—C40—N41—C42	−174.6 (15)
C18—N19—C20—C21	29.8 (10)	C40—N41—C42—C43	−29 (2)
N19—C20—C21—C22	−53.0 (8)	N41—C42—C43—C44	50.9 (15)
C18—N12—C22—C21	−18.5 (9)	C40—N34—C44—C43	21 (4)
C13—N12—C22—C21	161.1 (6)	C35—N34—C44—C43	−156.7 (18)
C20—C21—C22—N12	48.4 (9)	C42—C43—C44—N34	−48 (2)
C29—N23—C24—C25	70.8 (8)	C40A—N34A—C35A—C36A	69 (4)
C33—N23—C24—C25	−107.4 (7)	C44A—N34A—C35A—C36A	−105 (3)
N23—C24—C25—C26	−78.4 (8)	N34A—C35A—C36A—C37A	−84 (2)
C24—C25—C26—C27	58.7 (8)	C35A—C36A—C37A—C38A	65 (3)
C25—C26—C27—C28	−61.5 (8)	C36A—C37A—C38A—C39A	−64 (3)
C26—C27—C28—C29	80.3 (7)	C37A—C38A—C39A—C40A	81 (2)
C33—N23—C29—N30	−8.1 (10)	C35A—N34A—C40A—N41A	176 (3)
C24—N23—C29—N30	173.8 (6)	C44A—N34A—C40A—N41A	−10 (6)
C33—N23—C29—C28	171.9 (6)	C35A—N34A—C40A—C39A	0 (6)
C24—N23—C29—C28	−6.2 (10)	C44A—N34A—C40A—C39A	173 (3)
C31—N30—C29—N23	−6.3 (10)	C38A—C39A—C40A—N41A	117 (2)
C31—N30—C29—C28	173.7 (6)	C38A—C39A—C40A—N34A	−66 (4)
C27—C28—C29—N23	−62.7 (8)	N34A—C40A—N41A—C42A	6 (5)
C27—C28—C29—N30	117.3 (7)	C39A—C40A—N41A—C42A	−177.6 (18)
C29—N30—C31—C32	37.4 (9)	C40A—N41A—C42A—C43A	26 (3)
N30—C31—C32—C33	−53.5 (9)	N41A—C42A—C43A—C44A	−51 (2)
C29—N23—C33—C32	−12.0 (10)	C40A—N34A—C44A—C43A	−18 (5)
C24—N23—C33—C32	166.2 (6)	C35A—N34A—C44A—C43A	156 (3)
C31—C32—C33—N23	42.8 (9)	C42A—C43A—C44A—N34A	49 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N19—H19···I9ⁱ	0.88	2.81	3.632 (5)	156
N41—H41···I6ⁱⁱ	0.88	2.91	3.735 (13)	157
N41—H41···I8ⁱⁱ	0.88	3.21	3.663 (14)	115
N41A—H41A···I6ⁱⁱ	0.88	2.62	3.492 (15)	169

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2.

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