research communications
9H17N2)3[Bi2I9]
of (CaDepartment of Chemistry, University of Reading, Whiteknights, Reading, RG6 6DX, UK
*Correspondence e-mail: p.vaqueiro@reading.ac.uk
Single crystals of tris(2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium) tri-μ2-iodido-bis[triiodidobismuth(III)], (C9H17N2)3[Bi2I9], were prepared by a solvothermal method, heating a mixture of BiI3, KI, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and ethanol at 443 K for six days. The of the title compound, which crystallizes in the monoclinic P21/c, contains one [Bi2I9]3− anion and three protonated DBUH+ moieties. The dinuclear [Bi2I9]3− anions, which are composed of face-sharing BiI63− octahedra, are packed in columns parallel to the [010] direction, and separated by protonated DBUH+ moieties. The optical band gap of (C9H7N2)3Bi2I9 is 2.1 eV.
Keywords: crystal structure; iodobismuthate; photovoltaic materials.
CCDC reference: 2100182
1. Chemical context
In recent years, hybrid bismuth halides have attracted considerable attention owing to their interesting physical properties (Adonin et al., 2016), including luminescence (Adonin et al., 2015), non-linear optical effects (Bi et al., 2008) and thermochromism (García-Fernández et al., 2018). Moreover, the lack of stability and the toxicity of lead halide perovskites has stimulated research efforts into bismuth-containing halides as stable and environmentally friendly alternatives for photovoltaic applications (Wu et al., 2020). However, bismuth-containing hybrid halides, such as (CH3NH3)3Bi2I9 (Eckhardt et al., 2016), often adopt low-dimensional structures, which in most cases result in larger band gaps than those of lead halide perovskites (Wang et al., 2020). Examples of two- or three-dimensional structures are very rare, and include a two-dimensional metal-deficient perovskite, (H2AEQT)Bi2/3I4 (AEQT = 5,5′′′'-bis(aminoethyl)-2,2′:5′,2′′:5′′,2′′′-quaterthiophene) (Mitzi, 2000) and the two-dimensional mixed halide (TMP)1.5[Bi2I7Cl2]4 (TMP = N,N,N′,N′-tetramethylpiperazine) (Li et al., 2017). The vast majority of hybrid bismuth halides contain zero-dimensional units, which are either discrete polynuclear or mononuclear anionic units, depending on the synthetic conditions and the nature of the organic counter-cations (Wu et al., 2009). In these materials, the Bi3+ cation typically adopts a distorted octahedral coordination, either forming mononuclear anions or polynuclear anions in which octahedra share edges or faces. Dinuclear species, such as [Bi2I8]2−, [Bi2I9]3− and [Bi2I10]4−, are one of the most widespread types of bismuth-halide units (Adonin et al., 2016).
2. Structural commentary
The 9H7N2)3Bi2I9 comprises three protonated DBUH+ cations, one of which is disordered (see Refinement), and one [Bi2I9]3− anion (Fig. 1). The two Bi3+ cations found in the [Bi2I9]3− unit are octahedrally coordinated by six iodides, with Bi—I distances ranging between 2.9532 (4) and 3.2788 (4) Å. Each BiI63− octahedron shares one face with a second octahedron, forming a dinuclear unit, [Bi2I9]3−. The Bi—I distances for the bridging μ2-I− anions, which range between 3.1405 (5) and 3.2788 (4) Å, are significantly longer than those for the terminal iodides [2.9532 (4) to 2.9908 (5) Å]. The angles for Bi3+—μ2-I−—Bi3+ range from 78.144 (9) to 80.095 (10)°, while those for terminal I−—Bi 3+—μ2-I− take values between 85.283 (13) and 97.725 (12)°. The face-sharing arrangement of BiI63− octahedra and the distances and angles are similar to those found in other compounds containing [Bi2I9]3− anions, such as (CH3NH3)3Bi2I9 (Eckhardt et al., 2016) or (C3H5N2)3Bi2I9 (Węcławik et al., 2016).
of (C3. Supramolecular features
The [Bi2I9]3− dinuclear units are packed in columns parallel to the [010] direction (Fig. 2), separated by the protonated DBUH+ cations. There are no short I⋯I distances between the [Bi2I9]3− anions, implying that there are limited interactions that could lead to extended electronic delocalization.
As shown in Table 1, there is hydrogen bonding between the amine functional groups in the DBU moieties and the [Bi2I9]3− dinuclear units. It should be noted that H30 does not form a hydrogen bond. This may be related to the fact that N30 is almost equidistant to I2, I5, I7 and I11. In addition, there are also short contacts of the type C—H⋯I. Hirshfeld surface analysis was performed using Crystal Explorer 17 (Turner et al., 2017), with standard resolution of the dnorm surfaces. A number of short H⋯I contacts are highlighted in red in the Hirshfeld surfaces for the DBU cations and the [Bi2I9]3− anion (Fig. 3). Examination of the fingerprint plots for the DBUH+ cations (see supporting information), resolved into H⋯H and H⋯I contacts, reveals that approximately 30% of the surface area corresponds to H⋯I contacts, with the remaining area corresponding to H⋯H interactions.
4. Database survey
A search in the Cambridge Structural Database (CSD Version 2020.3, December 2020; Groom et al., 2016) reveals that there are numerous compounds containing the dinuclear [Bi2I9]3− anion, also found in the compound reported here. This includes examples in which the counter-cation is an organic moiety, such as (CH3NH3)3Bi2I9 (Eckhardt et al., 2016) or (C3H5N2)3Bi2I9 (Węcławik et al., 2016), but also compounds in which the counter-cation is a transition-metal or a rare-earth complex, such as [Co(C2H8N2)3][Bi2I9] (Goforth et al., 2005) or [Ln(DMF)8][Bi2I9] (Ln = Y, Tb) (Mishra et al., 2012). The ubiquitous dinuclear [Bi2I9]3− anion has also been found in compounds containing two or more anions, including (C8H18N2)7(BiI6)2(Bi2I9)2·2I3 (Zhang et al., 2018), and in inorganic compounds like Cs3Bi2I9 (Arakcheeva et al., 2001).
5. Optical properties and thermal stability
UV–vis diffuse reflectance data (Fig. 4) were collected on hand-picked single crystals, using a Perkin Elmer Lambda 35 UV–vis spectrometer. BaSO4 was used as a standard. The optical band gap, which was estimated from the is 2.1 eV. Thermogravimetric analysis (TGA) was carried out using a TA-TGA Q50 instrument. Measurements (see supporting information) carried out under a flowing nitrogen atmosphere indicate that (C9H7N2)3Bi2I9 is stable up to 300°C.
6. Synthesis and crystallization
A mixture of BiI3 (1.1790 g, 2 mmol), KI (0.4490 g, 3 mmol), DBU (0.150 mL, 1 mmol) and ethanol (10 mL) was placed inside the Teflon liner of a 23 mL Parr autoclave. The autoclave was heated in an oven at 443 K for 6 days, using a heating and cooling rate of 0.1 K min−1. Following filtration, the collected solid product consisted of a mixture of red powder and crystals of the title compound. The powder X-ray diffraction pattern of the product (see supporting information), collected using a Bruker D8 Advance powder diffractometer (Cu Kα1, λ = 1.5406 Å), was in excellent agreement with the simulated diffraction pattern, based on the single-crystal Elemental analysis: Calculated values (%) for C27H51N6Bi2I9: C, 16.06; H, 2.55; N, 4.16. Found: C, 16.07; H, 2.42; N, 4.09. IR (νmax) cm−1: 2920, 2850 (C—H); 1640 (C=N).
7. Refinement
Crystal data, data collection and structure . All hydrogen atoms were positioned geometrically, with C—H = 0.99 Å (for methylene H atoms) and with N—H = 0.88 Å, and were refined with Uiso(H) = 1.2Ueq(C or N). The disordered DBUH+ cation has been refined using geometry (SAME) and Uij restraints (SIMU and RIGU) implemented in SHELXL. The ratio between the site occupancies of the two positions was refined to 57.1 (13):42.9 (13)%. The maximum/minimum of the difference electron density is located 1.10 and 1.13 Å from Bi3 and Bi1, respectively. The electron density maxima and minima (2.22 and −2.57 e Å−3) close to the heavy bismuth atoms can be ascribed to Fourier truncation ripples and/or non-ideal absorption correction.
details are summarized in Table 2Supporting information
CCDC reference: 2100182
https://doi.org/10.1107/S2056989021007799/jq2007sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021007799/jq2007Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989021007799/jq2007Isup4.cdx
Fingerprint plots, powder diffraction and TGA data. DOI: https://doi.org/10.1107/S2056989021007799/jq2007sup5.pdf
Data collection: CrysAlis PRO (Rigaku OD, 2019); cell
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).(C9H17N2)3[Bi2I9] | F(000) = 3592 |
Mr = 2019.79 | Dx = 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 |
XtaLAB Synergy, Dualflex, HyPix diffractometer | 11096 reflections with I > 2σ(I) |
ω scans | Rint = 0.034 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019) | θmax = 30.5°, θmin = 2.4° |
Tmin = 0.23, Tmax = 1.00 | h = −27→27 |
38319 measured reflections | k = −13→17 |
13780 independent reflections | l = −30→29 |
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(Fo2) + (0.0423P)2 + 1.9329P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
13780 reflections | Δρmax = 2.22 e Å−3 |
497 parameters | Δρmin = −2.57 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | 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) |
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) |
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) |
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. |
Acknowledgements
The University of Reading is acknowledged for access to the Chemical Analysis Facility (CAF). Mr Nick Spencer is thanked for his assistance with the collection of the X-ray diffraction data and Dr Pedro Rivas Ruiz for help with FT–IR and Thermogravimetric analysis.
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