research papers\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

IUCrJ
ISSN: 2052-2525

Enhancing hydrogen positions in X-ray structures of transition metal hydride complexes with dynamic quantum crystallography

crossmark logo

aBiological and Chemical Research Centre, Chemistry Department, University of Warsaw, Żwirki i Wigury 101, Warsaw 02-089, Poland
*Correspondence e-mail: magdalena.woinska@uw.edu.pl, kwozniak@chem.uw.edu.pl

Edited by A. Fitch, ESRF, France (Received 25 May 2023; accepted 31 October 2023; online 22 November 2023)

Hirshfeld atom refinement (HAR) is a method which enables the user to obtain more accurate positions of hydrogen atoms bonded to light chemical elements using X-ray data. When data quality permits, this method can be extended to hydrogen-bonded transition metals (TMs), as in hydride complexes. However, addressing hydrogen thermal motions with HAR, particularly in TM hydrides, presents a challenge. At the same time, proper description of thermal vibrations can be vital for determining hydrogen positions correctly. In this study, we employ tools such as SHADE3 and Normal Mode Refinement (NoMoRe) to estimate anisotropic displacement parameters (ADPs) for hydrogen atoms during HAR and IAM refinements performed for seven structures of TM (Fe, Ni, Cr, Nb, Rh and Os) and metalloid (Sb) hydride complexes for which both the neutron and the X-ray structures have been determined. A direct comparison between neutron and HAR/SHADE3/NoMoRe ADPs reveals that the similarity between neutron hydrogen ADPs and those estimated with NoMoRe or SHADE3 is significantly higher than when hydrogen ADPs are refined with HAR. Regarding TM—H bond lengths, traditional HAR exhibits a slight advantage over the other methods. However, combining NoMoRe/SHADE3 with HAR results in a minor decrease in agreement with neutron TM—H bond lengths. For the Cr complex, for which high-resolution X-ray data were collected, an investigation of resolution-related effects was possible.

1. Introduction

Transition metal (TM) bound hydrides are compounds which play a crucial role in important chemical reactions and have various potential applications. They serve as catalysts or intermediate compounds in energy conversion processes (Bullock et al., 2014[Bullock, R. M., Appel, A. M. & Helm, M. L. (2014). Chem. Commun. 50, 3125-3143.]; Rakowski Dubois & Dubois, 2009[Rakowski Dubois, M. & Dubois, D. L. (2009). Acc. Chem. Res. 42, 1974-1982.]; Thoi et al., 2013[Thoi, V. S., Sun, Y., Long, J. R. & Chang, C. J. (2013). Chem. Soc. Rev. 42, 2388-2400.]), catalytic hydrogenation and reactions involving C—H bond activation (Hilt, 2014[Hilt, G. (2014). ChemCatChem, 6, 2484-2485.]; Lyons & Sanford, 2010[Lyons, T. W. & Sanford, M. S. (2010). Chem. Rev. 110, 1147-1169.]; Labinger & Bercaw, 2002[Labinger, J. A. & Bercaw, J. E. (2002). Nature, 417, 507-514.]; Choi et al., 2011[Choi, J., MacArthur, A. H. R., Brookhart, M. & Goldman, A. S. (2011). Chem. Rev. 111, 1761-1779.]). Additionally, many TM hydrides can be used as hydrogen storage materials (Schlapbach & Züttel, 2001[Schlapbach, L. & Züttel, A. (2001). Nature, 414, 353-358.]; Fukuzumi & Suenobu, 2013[Fukuzumi, S. & Suenobu, T. (2013). Dalton Trans. 42, 18-28.]; Langmi et al., 2014[Langmi, H. W., Ren, J., North, B., Mathe, M. & Bessarabov, D. (2014). Electrochim. Acta, 128, 368-392.]) and exhibit superconductivity or high-temperature superconductivity (Semenok et al., 2020[Semenok, D. V., Kruglov, I. A., Savkin, I. A., Kvashnin, A. G. & Oganov, A. R. (2020). Curr. Opin. Solid State Mater. Sci. 24, 100808.]; Du et al., 2021[Du, M., Zhang, Z., Song, H., Yu, H., Cui, T., Kresin, V. Z. & Duan, D. (2021). Phys. Chem. Chem. Phys. 23, 6717-6724.]), e.g. Pd and Pd–Ni hydrides (Skoskiewicz, 1972[Skoskiewicz, T. (1972). Phys. Status Solidi A, 11, K123-K126.]), V hydrides (Li & Peng, 2017[Li, X. & Peng, F. (2017). Inorg. Chem. 56, 13759-13765.]), Cr hydrides (Yu et al., 2015[Yu, S., Jia, X., Frapper, G., Li, D., Oganov, A. R., Zeng, Q. & Zhang, L. (2015). Sci. Rep. 5, 17764.]), Nb hydrides, Ta hydrides (Hubbard Horn & Ziegler, 1947[Horn, F. H. & Ziegler, W. T. (1947). J. Am. Chem. Soc. 69, 2762-2769.]), and Th hydrides (Satterthwaite & Toepke, 1970[Satterthwaite, C. B. & Toepke, I. L. (1970). Phys. Rev. Lett. 25, 741-743.]). This interesting class of compounds presents a challenge for X-ray crystallography and its most popular method, the Independent Atom Model (IAM) (Compton, 1915[Compton, A. H. (1915). Nature, 95, 343-344.]). The limitations arise from the simplified spherical electron density model, which cannot correctly describe aspherical electron density deformations due to the presence of lone electron pairs and bond formation, let alone other interactions between/within molecules in the crystals. Moreover, in TM hydrides, the weak X-ray diffraction signal from the hydrogen atom is screened by the strong signal from the electron-rich metal atom.

Hirshfeld atom refinement (HAR) (Jayatilaka & Dittrich, 2008[Jayatilaka, D. & Dittrich, B. (2008). Acta Cryst. A64, 383-393.]; Capelli et al., 2014[Capelli, S. C., Bürgi, H.-B., Dittrich, B., Grabowsky, S. & Jayatilaka, D. (2014). IUCrJ, 1, 361-379.]) is a method utilizing the Hirshfeld model of electron density (Hirshfeld, 1977[Hirshfeld, F. L. (1977). Theor. Chim. Acta, 44, 129-138.]) which accounts for the aspherical features of atomic electron density. HAR has evolved significantly in recent years, incorporating features like disorder refinement, solvent modelling to mimic the crystal environment (Kleemiss et al., 2021[Kleemiss, F., Dolomanov, O. V., Bodensteiner, M., Peyerimhoff, N., Midgley, L., Bourhis, L. J., Genoni, A., Malaspina, L. A., Jayatilaka, D., Spencer, J. L., White, F., Grundkötter-Stock, B., Steinhauer, S., Lentz, D., Puschmann, H. & Grabowsky, S. (2021). Chem. Sci. 12, 1675-1692.]), various electron density partitioning methods (Chodkiewicz et al., 2020[Chodkiewicz, M. L., Woińska, M. & Woźniak, K. (2020). IUCrJ, 7, 1199-1215.]), fragmentation helpful in tackling large molecules and network compounds (Chodkiewicz et al., 2022[Chodkiewicz, M., Pawlędzio, S., Woińska, M. & Woźniak, K. (2022). IUCrJ, 9, 298-315.]), and finally periodic boundary conditions (Ruth et al., 2022[Ruth, P. N., Herbst-Irmer, R. & Stalke, D. (2022). IUCrJ, 9, 286-297.]). Compared with IAM, HAR shows remarkable improvement in accuracy and precision of positions of hydrogen atoms bonded to lighter chemical elements based on standard-resolution (d = 0.83 Å) good-quality X-ray data (data with hydrogen positions that can be freely refined with IAM). Although IAM underestimates the lengths of X—H bonds typical for crystals of organic compounds on average by 0.12 Å, compared with neutron bond lengths, mean X—H bond lengths obtained with HAR are underestimated by on average only 0.014 Å (Jha et al., 2020[Jha, K. K., Gruza, B., Kumar, P., Chodkiewicz, M. L. & Dominiak, P. M. (2020). Acta Cryst. B76, 296-306.]; Woińska et al., 2016[Woińska, M., Grabowsky, S., Dominiak, P. M., Woźniak, K. & Jayatilaka, D. (2016). Sci. Adv. 2, e1600192.]). However, the ability of HAR to refine anisotropic displacement parameters (ADPs) of hydrogen atoms is subject to data quality (Malaspina et al., 2020[Malaspina, L. A., Hoser, A. A., Edwards, A. J., Woińska, M., Turner, M. J., Price, J. R., Sugimoto, K., Nishibori, E., Bürgi, H.-B., Jayatilaka, D. & Grabowsky, S. (2020). CrystEngComm, 22, 4778-4789.]; Woinska et al., 2019[Woinska, M., Wanat, M., Taciak, P., Pawinski, T., Minor, W. & Wozniak, K. (2019). IUCrJ, 6, 868-883.]). HAR has been successfully used for processing X-ray data collected for TM complexes, including TM hydrides (Woińska et al., 2016[Woińska, M., Grabowsky, S., Dominiak, P. M., Woźniak, K. & Jayatilaka, D. (2016). Sci. Adv. 2, e1600192.], 2021[Woińska, M., Chodkiewicz, M. L. & Woźniak, K. (2021). Chem. Commun. 57, 3652-3655.], 2023[Woińska, M., Pawlędzio, S., Chodkiewicz, M. L. & Woźniak, K. (2023). J. Phys. Chem. A, 127, 3020-3035.]; Kleemiss et al., 2021[Kleemiss, F., Dolomanov, O. V., Bodensteiner, M., Peyerimhoff, N., Midgley, L., Bourhis, L. J., Genoni, A., Malaspina, L. A., Jayatilaka, D., Spencer, J. L., White, F., Grundkötter-Stock, B., Steinhauer, S., Lentz, D., Puschmann, H. & Grabowsky, S. (2021). Chem. Sci. 12, 1675-1692.]; Holsten et al., 2021[Holsten, S. A., Malaspina, L., Kleemiss, F., Mebs, S., Hupf, E., Grabowsky, S. & Beckmann, J. (2021). Organometallics, 40, 2027-2038.]). It allows modelling of electron density of the TM by means of very exact quantum mechanical calculations, with the possibility of including relativistic effects (Kleemiss et al., 2021[Kleemiss, F., Dolomanov, O. V., Bodensteiner, M., Peyerimhoff, N., Midgley, L., Bourhis, L. J., Genoni, A., Malaspina, L. A., Jayatilaka, D., Spencer, J. L., White, F., Grundkötter-Stock, B., Steinhauer, S., Lentz, D., Puschmann, H. & Grabowsky, S. (2021). Chem. Sci. 12, 1675-1692.]; Holsten et al., 2021[Holsten, S. A., Malaspina, L., Kleemiss, F., Mebs, S., Hupf, E., Grabowsky, S. & Beckmann, J. (2021). Organometallics, 40, 2027-2038.]; Bučinský et al., 2016[Bučinský, L., Jayatilaka, D. & Grabowsky, S. (2016). J. Phys. Chem. A, 120, 6650-6669.], 2019[Bučinský, L., Jayatilaka, D. & Grabowsky, S. (2019). Acta Cryst. A75, 705-717.]; Malaspina et al., 2019[Malaspina, L. A., Wieduwilt, E. K., Bergmann, J., Kleemiss, F., Meyer, B., Ruiz-López, M. F., Pal, R., Hupf, E., Beckmann, J., Piltz, R. O., Edwards, A. J., Grabowsky, S. & Genoni, A. (2019). J. Phys. Chem. Lett. 10, 6973-6982.]; Pawlędzio et al., 2021[Pawlędzio, S., Malinska, M., Woińska, M., Wojciechowski, J., Andrade Malaspina, L., Kleemiss, F., Grabowsky, S. & Woźniak, K. (2021). IUCrJ, 8, 608-620.]; Woińska et al., 2023[Woińska, M., Pawlędzio, S., Chodkiewicz, M. L. & Woźniak, K. (2023). J. Phys. Chem. A, 127, 3020-3035.]).

Collecting high-quality X-ray data for crystals of TM hydride complexes is difficult due to high absorption and radiation damage. Neutron structures, crucial for validating hydrogen positions and thermal motions, are even scarcer. Nonetheless, in our previous work we refined ten X-ray datasets of TM hydride complexes deposited in the Cambridge Structural Database (CSD), each with the corresponding neutron structure. For five of the structures HAR outperformed IAM in terms of agreement of the TM—H bond lengths with the neutron values. We ranked the structures by quality of the X-ray and neutron data and quality of refinement, clearly showing the superiority of HAR for the higher-quality structures and the surprisingly good performance of IAM for the lowest-quality datasets. Our previous study also explored the impact of various DFT functionals, basis sets, relativistic effects and interactions with the surrounding molecules in the crystal. We tentatively considered the idea of estimating hydrogen ADPs using the SHADE2 server (Madsen, 2006[Madsen, A. Ø. (2006). J. Appl. Cryst. 39, 757-758.]) but successfully coupled it with HAR for only one structure. Using more advanced methods stemming from SHADE2, such as SHADE3 (Madsen & Hoser, 2014[Madsen, A. Ø. & Hoser, A. A. (2014). J. Appl. Cryst. 47, 2100-2104.]) and Normal Mode Refinement (NoMoRe) (Hoser & Madsen, 2016[Hoser, A. A. & Madsen, A. Ø. (2016). Acta Cryst. A72, 206-214.], 2017[Hoser, A. A. & Madsen, A. Ø. (2017). Acta Cryst. A73, 102-114.]) was beyond the scope of our previous study due to computational demands. This work is a continuation of our previous study, focusing on SHADE3 and NoMoRe to estimate anisotropic thermal motions of hydrogen atoms and investigate their influence on positions of hydrogen atoms and compare ADPs obtained with various methods. Furthermore, we examine high-resolution X-ray data of a chromium complex (Macchi et al., 2005[Macchi, P., Donghi, D. & Sironi, A. (2005). J. Am. Chem. Soc. 127, 16494-16504.]) with the neutron data collected at a similar temperature (Petersen et al., 1981[Petersen, J. L., Brown, R. K. & Williams, J. M. (1981). Inorg. Chem. 20, 158-165.]). This allows us to investigate the impact of resolution on atomic thermal motions determined with HAR, IAM, SHADE3 and NoMoRe and the influence on the position of the hydrogen atom bonded to the TM atom. The latter issue has already been investigated by Kleemiss et al. (2021[Kleemiss, F., Dolomanov, O. V., Bodensteiner, M., Peyerimhoff, N., Midgley, L., Bourhis, L. J., Genoni, A., Malaspina, L. A., Jayatilaka, D., Spencer, J. L., White, F., Grundkötter-Stock, B., Steinhauer, S., Lentz, D., Puschmann, H. & Grabowsky, S. (2021). Chem. Sci. 12, 1675-1692.]); however, there was no clear conclusion whether more information resulting from higher resolution was superior to better overall quality of low-resolution data.

The SHADE2 approach (Madsen, 2006[Madsen, A. Ø. (2006). J. Appl. Cryst. 39, 757-758.]) divides atomic thermal motion into the uncorrelated internal and external rigid body components. The external motion of hydrogen atoms is obtained from TLS (translation-libration-screw) analysis (Schomaker & Trueblood, 1968[Schomaker, V. & Trueblood, K. N. (1968). Acta Cryst. B24, 63-76.]) of the non-hydrogen atom framework as a rigid body and the internal part comes from the library of internal mean square displacements (MSDs) derived from neutron data. ADPs estimated with SHADE2 are usually in good agreement with neutron-derived ADPs for hydrogen atoms involved in typical covalent bonds (Madsen & Hoser, 2014[Madsen, A. Ø. & Hoser, A. A. (2014). J. Appl. Cryst. 47, 2100-2104.]); however, inaccuracies can occur for atoms involved in medium and strong hydrogen bonds or hydrogen atoms bonded to TMs. SHADE3 (Madsen & Hoser, 2014[Madsen, A. Ø. & Hoser, A. A. (2014). J. Appl. Cryst. 47, 2100-2104.]) overcomes this problem by deriving the MSDs from normal-mode frequencies of the high-frequency vibrations obtained from periodic calculations at the Γ-point of the Brillouin zone or from spectroscopic experiments. NoMoRe (Hoser & Madsen, 2016[Hoser, A. A. & Madsen, A. Ø. (2016). Acta Cryst. A72, 206-214.], 2017[Hoser, A. A. & Madsen, A. Ø. (2017). Acta Cryst. A73, 102-114.]) goes further, using all the normal-mode frequencies to estimate atomic thermal vibrations: the high-frequency ones are used to obtain the MSDs and the low-frequency ones, which are difficult to calculate accurately, are subject to NoMoRe. In this procedure, the scaling factors of the low-frequency normal modes are refined against diffraction data alternately with atomic coordinates in order to minimize wR2. The TLS analysis assumes that 6Z (where Z is the number of asymmetric units in the unit cell) low-frequency normal modes correspond with the external vibrations; however, in practice, the number of refined low-frequency modes has to be adjusted.

NoMoRe has been successfully used to estimate hydrogen ADPs and thermodynamic properties for a number of crystal structures of simple organic compounds, such as urea (Hoser & Madsen, 2016[Hoser, A. A. & Madsen, A. Ø. (2016). Acta Cryst. A72, 206-214.]); L-alanine, naphthalene and xylitol (Hoser & Madsen, 2017[Hoser, A. A. & Madsen, A. Ø. (2017). Acta Cryst. A73, 102-114.]); yellow and white polymorphs of di­methyl 3,6-di­chloro-2,5-di­hydroxy­terephthalate (Kofoed et al., 2019[Kofoed, P. M., Hoser, A. A., Diness, F., Capelli, S. C. & Madsen, A. Ø. (2019). IUCrJ, 6, 558-571.]); L-alanine (Sovago et al., 2020[Sovago, I., Hoser, A. A. & Madsen, A. Ø. (2020). Acta Cryst. A76, 32-44.]); urea, the α- and β-glycine polymorphs, benzoic acid, and 4′-hy­droxy­aceto­phenone (Hoser et al., 2021[Hoser, A. A., Sztylko, M., Trzybiński, D. & Madsen, A. Ø. (2021). Chem. Commun. 57, 9370-9373.]); and the pyrazinamide polymorphs (Hoser et al., 2022[Hoser, A. A., Rekis, T. & Madsen, A. Ø. (2022). Acta Cryst. B78, 416-424.]). SHADE3 has been applied to the crystal structures of 1-methyl­uracil, α -glycine, L-alanine, 2-methyl-4-nitro­aniline, xylitol and Proton Sponge (Madsen & Hoser, 2014[Madsen, A. Ø. & Hoser, A. A. (2014). J. Appl. Cryst. 47, 2100-2104.]). Both techniques have also been used to estimate hydrogen ADPs for HAR (Malaspina et al., 2020[Malaspina, L. A., Hoser, A. A., Edwards, A. J., Woińska, M., Turner, M. J., Price, J. R., Sugimoto, K., Nishibori, E., Bürgi, H.-B., Jayatilaka, D. & Grabowsky, S. (2020). CrystEngComm, 22, 4778-4789.]; Wanat et al., 2021[Wanat, M., Malinska, M., Hoser, A. A. & Woźniak, K. (2021). Molecules, 26, 3730.]). This work is an attempt to apply SHADE3 and NoMoRe to TM hydride complexes, aiming to improve hydrogen positions, especially for TM—H bonds, and compare the ADPs obtained with various methods to the neutron data. It also explores the computational feasibility of applying these methods to TM hydride complexes.

2. Results and discussion

2.1. Experimental data and previous results

In our previous research (Woińska et al., 2023[Woińska, M., Pawlędzio, S., Chodkiewicz, M. L. & Woźniak, K. (2023). J. Phys. Chem. A, 127, 3020-3035.]), we performed HAR for ten metal–organic complexes featuring TM hydrogen bonds with both known X-ray structures and known neutron structures. The structures were ranked according to the quality of the neutron and X-ray datasets (based on resolution, completeness and Rint) and refinement (evaluated according to R, wR2, goodness of fit and residual density range) performed, leading to the final joint data- and refinement-quality X-ray (HAR)–neutron and X-ray (IAM)–neutron rankings. Structures were ordered from worst to best according to a given quantity and the score was equal to the position in the ranking. If a certain quantity used in the ranking procedure was unknown, the structure automatically obtained the lowest position in the ranking with respect to this quantity. The obtained scores were summed for each structure separately, leading to the data- and refinement-quality ranking, separate for the neutron and X-ray data. Next, the neutron and X-ray rankings were combined to form the final joint X-ray and neutron data and refinement quality ranking. For the top-ranked structures, HAR significantly improved agreement between the TM—H bond lengths and the neutron values compared with IAM. However, for half of the structures, particularly those lower in the ranking, HAR did not provide improvement and sometimes deteriorated the results in comparison with IAM. Consequently, one could ask whether further progression in the determination of positions of hydrogen atoms bonded to TMs is possible with HAR. Since refinement of hydrogen ADPs is often highlighted as a weakness of HAR, this study explores combining HAR with advanced models of hydrogen ADPs such as SHADE3 and NoMoRe. Six previously studied structures were chosen for this purpose. The selected structures are marked with the following REFCODEs: QOSZON (Ho et al., 2003[Ho, N. N., Bau, R. & Mason, S. A. (2003). J. Organomet. Chem. 676, 85-88.]) neutron, (Arion et al., 2001[Arion, V., Brunet, J.-J. & Neibecker, D. (2001). Inorg. Chem. 40, 2628-2630.]) X-ray; SITKUB (Lam et al., 2003[Lam, W. H., Shimada, S., Batsanov, A. S., Lin, Z., Marder, T. B., Cowan, J. A., Howard, J. A. K., Mason, S. A. & McIntyre, G. J. (2003). Organometallics, 22, 4557-4568.]), ZEYVAA (Bakhmutov et al., 2000[Bakhmutov, V. I., Howard, J. A. K., Keen, D. A., Kuzmina, L. G., Leech, M. A., Nikonov, G. I., Vorontsov, E. V. & Wilson, C. C. (2000). J. Chem. Soc. Dalton Trans. pp. 1631-1635.]) neutron, (Nikonov et al., 1995[Nikonov, G. I., Kuzmina, L. G., Lemenovskii, D. A. & Kotov, V. V. (1995). J. Am. Chem. Soc. 117, 10133-10134.]) X-ray; GOJNIF (Cammarota et al., 2019[Cammarota, R. C., Xie, J., Burgess, S. A., Vollmer, M. V., Vogiatzis, K. D., Ye, J., Linehan, J. C., Appel, A. M., Hoffmann, C., Wang, X., Young, V. G. & Lu, C. C. (2019). Chem. Sci. 10, 7029-7042.]), TIWXOP (Schwamm et al., 2019[Schwamm, R. J., Edwards, A. J., Fitchett, C. M. & Coles, M. P. (2019). Dalton Trans. 48, 2953-2958.]), XAXMEP (Webster et al., 2005[Webster, C. E., Gross, C. L., Young, D. M., Girolami, G. S., Schultz, A. J., Hall, M. B. & Eckert, J. (2005). J. Am. Chem. Soc. 127, 15091-15101.]) neutron (Gross & Girolami, 2007[Gross, C. L. & Girolami, G. S. (2007). Organometallics, 26, 1658-1664.]) X-ray. Additionally, the high-resolution X-ray structure of the complex containing a Cr—H—Cr bridging bond, KCPTCR (Petersen et al., 1981[Petersen, J. L., Brown, R. K. & Williams, J. M. (1981). Inorg. Chem. 20, 158-165.]) neutron, (Macchi et al., 2005[Macchi, P., Donghi, D. & Sironi, A. (2005). J. Am. Chem. Soc. 127, 16494-16504.]) X-ray, was included to examine the role of data resolution. The ranking of structures from the previous study was supplemented with KCPTCR_std (refinement against dataset truncated to the resolution 0.59 Å−1) and KCPTCR_max (refinement against the full dataset) structures. The order of structures in the joint X-ray and neutron data and refinement quality ranking, from best to worst, is as follows: (1) QOSZON, (2) KCPTCR_std, (3) GOJNIF, (4) SITKUB, (5) KCPTCR_max, (6) TIWXOP, (7) ZEYVAA, (8) XAXMEP. All the investigated structures are depicted in Fig. 1[link]. One must bear in mind that this study is based on quite a small set of structures with varying quality of both neutron and X-ray datasets.

[Figure 1]
Figure 1
Schematic of the investigated structures with heavy metals bonded to hydrogen atoms marked.

2.2. Refinement types and theoretical calculations

The DiSCaMB library (Chodkiewicz et al., 2018[Chodkiewicz, M. L., Migacz, S., Rudnicki, W., Makal, A., Kalinowski, J. A., Moriarty, N. W., Grosse-Kunstleve, R. W., Afonine, P. V., Adams, P. D. & Dominiak, P. M. (2018). J. Appl. Cryst. 51, 193-199.]) was used for HAR in various versions, all of which employed the same procedure of obtaining aspherical atomic scattering factors: the DFT method with B3LYP functional was used (Becke, 1988[Becke, A. D. (1988). Phys. Rev. A, 38, 3098-3100.]; Lee et al., 1988[Lee, C., Yang, W. & Parr, R. G. (1988). Phys. Rev. B, 37, 785-789.]) and interactions within the crystal were included by surrounding the central molecule with a cluster of Hirshfeld partition-derived atomic charges and dipoles for all molecules with at least one atom within 8 Å from the central molecule. The basis set was chosen based on the TM atom to optimize TM—H bond lengths, as described in our previous study (Woińska et al., 2023[Woińska, M., Pawlędzio, S., Chodkiewicz, M. L. & Woźniak, K. (2023). J. Phys. Chem. A, 127, 3020-3035.]) and detailed in Table 1[link]. Convergence was reached when the maximum (parameter shift/sigma) was less than 0.001. Geometry optimization in the gas phase in previous work showed that the singlet state had the lowest energy for the compounds considered, so only this spin state was taken into account. In the case of KCPTCR, only geometry optimization for the singlet state was feasible. All refinements for this structure were performed against the full dataset (KCPTCR_max) and against the dataset truncated to a resolution of 0.59 Å−1, which is equivalent to θmax = 25° (KCPTCR_std) for Mo Kα radiation.

Table 1
Basis sets used in HAR and in normal-mode frequency calculations in CRYSTAL, temperatures of data collection and treatment of hydrogen thermal motions in the investigated structures

In the case of HAR, the basis sets in the table were used for all atoms in the structure (unless otherwise stated). In the case of CRYSTAL calculations the basis sets in the table were used for the heavy metal atoms only, and for the remaining atoms the 6-31G(d,p) basis set was used.

    Basis set Temperature (K) Hydrogen thermal motions
REFCODE Metal HAR CRYSTAL X-ray Neutron HAR Neutron
KCPTCR Cr cc-pVDZ TZP 28 (2) 20 (1) Anisotropic Anisotropic
K cc-pVDZ TZP
QOSZON Fe cc-pVTZ 6-31G(d,p) 293 (2) 20 (2) Anisotropic Anisotropic
SITKUB Rh jorge-DZP jorge-DZP 120.15 20 (2) Anisotropic Isotropic
ZEYVAA Nb cc-pVTZ-DK cc-pVTZ-DK 173 (2) 100 Isotropic Anisotropic
XAXMEP Os jorge-DZP jorge-DZP 199 (2) 20 Isotropic Isotropic
TIWXOP Sb jorge-DZP jorge-DZP 120.01 (10) 120 Isotropic Anisotropic
GOJNIF Ni cc-pVTZ-DK 6-31G(d,p) 100 (2) 100 (2) Anisotropic Anisotropic
In cc-pVTZ-DK3 cc-pVTZ-DK3
Basis set used only for the In atom in HAR.
†Only the hydrogen atom bonded to Rh was refined anisotropically.

Various types of HAR were conducted with hydrogen ADPs fixed at the SHADE3/NoMoRe values. The refinements denoted HAR_SHADE3/HAR_NoMoRe involved using SHADE3/NoMoRe before each HAR cycle and refining until max(parameter shift/sigma) was below 1.0. The HAR_SHADE3 refinement for ZEYVAA was considered not converged since max(parameter shift/sigma) was oscillating and its values were much higher than 1.0. In refinements denoted HAR_SHADE3_1/HAR_NoMoRe_1, hydrogen ADPs were determined using SHADE3/NoMoRe only before the first HAR cycle and refinements continued until the maximum (parameter shift/sigma) was below 0.001. Additionally, IAM refinements using SHADE3 and NoMoRe were performed. Lastly, IAM and HAR with all hydrogen ADPs set to 0 (denoted IAM_0_HADPs and HAR_0_HADPs) were carried out. Although this is an unphysical model of thermal vibrations, it served as a boundary evaluation for the influence of the values of hydrogen ADPs on TM—H and X—H bond lengths and refinement statistics. Statistics describing all the refinements are provided in the supporting information (Figs. S1–S9 and Tables S2–S8) along with the computational details for SHADE3 and NoMoRe procedures.

2.3. Atomic thermal motions: similarity index

The similarity index S12 (Whitten & Spackman, 2006[Whitten, A. E. & Spackman, M. A. (2006). Acta Cryst. B62, 875-888.]) was used as a measure of similarity between thermal ellipsoids of a given atom obtained with different diffraction methods or models. S12 quantifies the non-overlapping part of probability densities of a given atom (differing due to different thermal motions) and is given by

[S_{12} = 100 \left(1 - R_{12} \right),]

where R12 is the overlap integral between the compared probability densities, calculated using only the values of the ADPs. S12 = 0 indicates perfect agreement, whereas 100 denotes the highest possible difference. Notably, S12 is more suitable for confirming high similarity between thermal motions, as even small differences at a level of 1 can result in noticeable visual differences in thermal ellipsoids. Moreover, depending on the estimated standard deviations (e.s.d.s) of ADPs, the e.s.d.s of S12 can be very high, making S12 an untrustworthy measure. Therefore, we use the mean S12 calculated for all hydrogen or non-hydrogen atoms in the molecule, along with their estimated errors calculated using error propagation. The estimated error of the mean S12 is lower meaning S12 is a more reliable measure of thermal motion similarity. In the supporting information, the values of S12 with e.s.d.s for individual atoms in all the structures are available (Figs. S10–S27), as well as the values of a mean S12 with the corresponding e.s.d.s of the mean (Figs. S28–S45).

HAR with anisotropically refined hydrogen thermal motions was attainable for four of the crystal structures. However, a few hydrogen atoms in these structures had to be refined isotropically (Tables S2–S8). For TIWXOP, XAXMEP and ZEYVAA, only isotropic refinement was possible. The results of HAR for these structures have been published in a previous study (Woińska et al., 2023[Woińska, M., Pawlędzio, S., Chodkiewicz, M. L. & Woźniak, K. (2023). J. Phys. Chem. A, 127, 3020-3035.]), with the exception of KCPTCR, which has not yet been treated with HAR, and GOJNIF, for which only isotropic HAR results were published. In the case of TIWXOP, the neutron dataset presented challenges, with large and distorted ellipsoids of anisotropically refined hydrogen atoms. One of the methyl groups in TIWXOP was significantly disordered, and only the hydrogen atoms of the largest component could be identified in the difference density map and refined isotropically, with the remaining nuclear density modelled as a ring of hydrogen nuclear density. The temperatures at which the neutron and the X-ray data for KCPTCR have been collected differ by only 8 K; therefore, we decided to compare the neutron thermal ellipsoids and those obtained from refinements against the X-ray data. Fig. 2[link] shows the structures of QOSZON and SITKUB obtained with HAR (anisotropic): HAR_NoMoRe and HAR_SHADE3. Fig. 3[link] displays the structures of XAXMEP and ZEYVAA obtained with HAR (isotropic): HAR_NoMoRe and HAR_SHADE3. Fig. 4[link] includes the X-ray-derived structures of TIWXOP, GOJNIF and KCPTCR along with the neutron structures.

[Figure 2]
Figure 2
Crystal structures of (a) QOSZON and (b) SITKUB obtained with HAR, HAR_NoMoRe and HAR_SHADE3. Thermal ellipsoids are depicted at the 50% probability level.
[Figure 3]
Figure 3
Crystal structures of (a) XAXMEP and (b) ZEYVAA obtained with HAR, HAR_NoMoRe and HAR_SHADE3 (HAR_SHADE3_1 for ZEYVAA). Thermal ellipsoids are depicted at the 50% probability level.
[Figure 4]
Figure 4
Crystal structures of (a) TIWXOP, (b) GOJNIF and (c) KCPTCR (high resolution) obtained based on the neutron and X-ray experiments (HAR, HAR_NoMoRe and HAR_SHADE3). Thermal ellipsoids are depicted at the 50% probability level.
2.3.1. Hydrogen ADPs from HAR_SHADE3(_1) versus HAR_NoMoRe(_1)

Average S12 values are close to 0 when comparing hydrogen ADPs obtained from HAR_SHADE3 and HAR_SHADE3_1, as well as HAR_NoMoRe and HAR_ NoMoRe_1. This means that iterative application of SHADE3 or NoMoRe during HAR does not influence the estimated values of hydrogen ADPs. We will now focus on the results of HAR_SHADE3 and HAR_NoMoRe, with the HAR_SHADE3_1 and HAR_NoMoRe_1 results available in the supporting information (Figs. S10–S71). The averaged S12 values, calculated between hydrogen ADPs obtained with HAR_SHADE3 and HAR_NoMoRe, are between 1 and 5 (see Table 2[link]) and reflect the differences in hydrogen ADPs resulting from variations in internal vibrations estimated with NoMoRe using experimental data, and those obtained with SHADE3 are based on theoretical calculations. The variability of averaged S12 for hydrogen atoms among the structures considered appears independent of the experimental temperature, position of the dataset in the ranking or the number of refined normal modes during NoMoRe. However, it noticeably decreases with the increasing number of hydrogen atoms in the structure.

Table 2
Averaged S12 comparing hydrogen ADPs obtained with HAR_SHADE3 and HAR_NoMoRe

The structures are ordered according to their position in the X-ray (HAR) neutron data-refinement-quality ranking from best to worst.

  Averaged S12 X-ray Temperature (K) Normal modes refined in NoMoRe
QOSZON 2.21 293 (2) 40
KCPTCR_std 1.25 28 (2) 20
GOJNIF 1.54 100 (2) 20
SITKUB 2.48 120.15 50
KCPTCR_max 1.28 28 (2) 20
TIWXOP 4.12 120.01 (10) 20
ZEYVAA 3.19 173 (2) 20
XAXMEP 1.47 199 (2) 70
†Results for HAR_SHADE3_1 and HAR_NoMoRe _1 (HAR_SHADE3 and HAR_NoMoRe did not converge).
2.3.2. Hydrogen ADPs from HAR versus HAR_SHADE3 and HAR_NoMoRe

The average S12 values between hydrogen ADPs obtained from HAR and HAR_NoMoRe are consistently lower than those from HAR and HAR_SHADE3. This is the consequence of the refinement of normal modes against experimental data (see Table 3[link]). Only for QOSZON is the average S12 value between hydrogen ADPs refined with HAR and those estimated with HAR_NoMoRe similar to the discrepancy between hydrogen ADPs from HAR_NoMoRe and HAR_SHADE3 (S12 = 2.67). The differences between hydrogen ADPs in QOSZON from HAR and HAR_SHADE3 are slightly higher, with S12 close to 5. For KCPTCR, SITKUB and GOJNIF, the S12 values between hydrogen ADPs obtained from HAR and HAR_NoMoRe/HAR_SHADE3 are already relatively high, ranging from 6.50 to 8.51 and 8.69 to 9.87, respectively. It is also noticeable that among the presented structures, S12 increases when the refinement of hydrogen ADPs with HAR becomes more problematic, i.e. the number of hydrogen atoms that have to be refined isotropically grows and also the shapes of refined hydrogen ellipsoids become more irregular. Refinement against high- and low-resolution data performed for KCPTCR reveals different behaviour of hydrogen ADPs from NoMoRe and SHADE3 – S12 slightly increases with decreasing resolution for NoMoRe and slightly decreases for SHADE3.

Table 3
Averaged S12 comparing hydrogen ADPs obtained with HAR and HAR_NoMoRe /HAR_SHADE3

Averaged S12 is given with its estimated error.

  HAR_NoMoRe HAR_ SHADE3
KCPTCR_max 6.00 ± 1.57 6.72 ± 1.61
KCPTCR_std 6.19 ± 1.46 6.66 ± 1.48
QOSZON 2.67 ± 0.77 4.75 ± 0.74
SITKUB 6.50 ± 2.16 8.51 ± 2.10
GOJNIF 8.69 ± 4.15 9.87 ± 4.08
2.3.3. Hydrogen and non-hydrogen ADPs from neutron versus HAR, HAR_SHADE3, HAR_NoMoRe and IAM

Based on the neutron data quality of KCPTCR, TIWXOP and GOJNIF, collected at the same or a similar temperature to the X-ray data, it was expected that TIWXOP would show the least favourable comparison (see Table 4[link]). Indeed, the average S12 for hydrogen atoms between neutron and HAR_NoMoRe is quite high, almost 9, and exceeds 11 between neutron and HAR_SHADE3. In the case of GOJNIF, for which the neutron structure is of much better quality, the average S12 between neutron and HAR_NoMoRe/HAR_SHADE3 is similar to the level of discrepancy between hydrogen ADPs from HAR_NoMoRe and HAR_SHADE3. Averaged S12 between the neutron and HAR hydrogen ADPs is high, almost 11. For KCPTCR, the results are better, with S12 between neutron and HAR hydrogen ADPs being similar to S12 between HAR and HAR_NoMoRe/HAR_SHADE3 hydrogen ADPs. These values indicate that for KCPTCR, NoMoRe in particular yields hydrogen thermal motions that are in quite good agreement with the neutron thermal motions, and their similarity is even higher on average than the similarity between NoMoRe and SHADE3. It can also be observed that S12 between neutron and HAR or SHADE3 hydrogen ellipsoids slightly decreases with lower data resolution, whereas in the case of NoMoRe, there is either a small increase or no significant difference. This outcome is expected, as the scattering factor of hydrogen atoms is very low at high resolution and high-resolution data do not add much information about hydrogen atoms.

Table 4
Averaged S12 comparing hydrogen ADPs obtained with neutron and HAR/HAR_NoMoRe/HAR_SHADE3

Averaged S12 is given its estimated error.

  HAR HAR_NoMoRe HAR_ SHADE3
KCPTCR_max 6.30 ± 1.72 0.98 ± 0.08 1.43 ± 0.07
KCPTCR_std 5.74 ± 1.54 1.05 ± 0.08 1.36 ± 0.07
TIWXOP 8.93 ± 1.12 11.47 ± 0.95
GOJNIF 10.89 ± 4.26 2.80 ± 1.62 3.55 ± 1.63

For non-hydrogen atoms, the S12 values between neutron ADPs and X-ray ADPs obtained with all investigated refinement techniques do not vary significantly across different structures (see Table 5[link]). In the case of GOJNIF, the averaged S12 reaches values up to 4. For GOJNIF, averaged S12 is slightly lower for all the versions of IAM than in the case of HAR, and there is generally not much variability observed in averaged S12 between different IAM or HAR versions [Fig. 4[link](b)]. In the case of TIWXOP, HAR (averaged S12 between 4.24 and 4.3) results in non-hydrogen ADPs more similar to the neutron ones than IAM (averaged S12 between 4.87 and 5.39) [Fig. 4[link](a)]. Regarding KCPTCR, using only low-resolution data significantly increases the S12 values between neutron and IAM ADPs of non-hydrogen atoms (from around 1.33–1.36 to 2.87–3.04), whereas the increase for HAR is very small [Fig. 4[link](c)]. Note that IAM requires high-resolution data to achieve the same level of agreement of non-hydrogen thermal motions with the neutron results as HAR can provide with standard-resolution data. Further comparison of the ADPs for KCPTCR based on refinement against the full high-resolution dataset to those in the structure resulting from X-ray data cut to the resolution limit equivalent to 2θ = 50° can be found in the supporting information.

Table 5
Averaged S12 comparing non-hydrogen ADPs obtained with neutron and HAR/HAR_NoMoRe/HAR_SHADE3

Averaged S12 is given with its estimated error.

  IAM IAM_NoMoRe IAM_SHADE3 IAM_0_HADPs HAR HAR_NoMoRe HAR_SHADE3 HAR_0_HADPs
KCPTCR_max 1.33 ± 0.52 1.36 ± 0.52 1.36 ± 0.52 1.36 ± 0.52 1.21 ± 0.52 1.22 ± 0.52 1.22 ± 0.52 1.23 ± 0.52
KCPTCR_std 2.96 ± 0.54 2.87 ± 0.54 2.88 ± 0.54 3.04 ± 0.55 1.32 ± 0.53 1.37 ± 0.52 1.37 ± 0.52 1.34 ± 0.53
TIWXOP 4.97 ± 0.59 4.87 ± 0.58 5.39 ± 0.59 5.20 ± 0.60 4.51 ± 0.56 4.24 ± 0.58 4.48 ± 0.55 4.83 ± 0.58
GOJNIF 3.84 ± 1.76 3.84 ± 1.76 3.88 ± 1.76 3.88 ± 1.77 3.98 ± 1.76 3.94 ± 1.77 3.99 ± 1.77 4.01 ± 1.78

2.4. The effect of data resolution on dynamic structure factors

Plotting the difference between the dynamic structure factor amplitudes [ΔFcalc = Fcalc(model1) − Fcalc(model2)] for the models allowed us to observe in which resolution ranges there are the highest differences between the models and how data truncation affects these differences. ΔFcalc between HAR and IAM for the full dataset [Fig. 5[link](a)] indicates the highest differences in low-resolution reflections (with a maximum between 0.2 and 0.3 Å−1) and a sharp decrease at sin(θ)/λ = 0.6 Å−1, which corresponds to the applied resolution cutoff. Applying the cutoff [Fig. 5[link](b)] has minimal effect on the low-resolution region, mainly reducing the concentration of diverging reflections, making HAR and IAM models slightly more similar. In both cases [Fig. 5[link](a) and 5[link](b)], ΔFcalc is quite symmetric relative to the x axis. Regarding how data trimming influences HAR and IAM individually [Figs. 5[link](c) and 5[link](d)], differences are less pronounced than between HAR and IAM, and the spread of ΔFcalc increases with higher resolution. HAR results in lower ΔFcalc compared with IAM. For both HAR and IAM, the KCPTCR_max structure tends to have slightly higher dynamic amplitudes of reflections than KCPTCR_std. The effect of thermal motions on dynamic structure factor amplitudes is very subtle; therefore, similar trends are observed for different techniques of estimating hydrogen thermal motion (Figs. S54–S59). Analogous effects for the remaining structures are presented in Figs. S60–S71.

[Figure 5]
Figure 5
The differences between the dynamic structure factors calculated in a given refinement versus resolution.

2.5. TM—H and X—H bond lengths obtained with various methods

The mean difference (MD) and mean absolute difference (MAD) between the neutron bond lengths and the X-ray bond lengths were calculated for the X—H and TM—H bonds (Fig. 6[link]). Combined standard deviation (c.s.d.) averaged over the bond lengths was used as a measure for uncertainty of MD and MAD and was calculated according to the formula

[{\rm c.s.d.} = \sqrt {{{\left({{\sigma_{\rm X}}} \right)}^2} + {{\left({{\sigma_{\rm N}}} \right)}^2}}]

where σX and σN are the estimated standard deviations of the X-ray and the neutron bond lengths, respectively. Aside from the plots, MD, MAD, MD/c.s.d. and MAD/c.s.d. values averaged for the X—H and TM—H bonds in all the structures are given in Tables 6[link] and 7[link]. The two-tailed Welch's t-test (Welch, 1947[Welch, B. L. (1947). Biometrika, 34, 28-35.]) was employed to assess the statistical significance of these differences.

Table 6
MD, MAD, MD/c.s.d. and MAD/c.s.d. values calculated between the neutron and the X-ray/optimized bond lengths averaged for X—H bonds in all the structures

Bold: statistically significant. Italics: not significant.

Method MD (Å) MAD (Å) MD/c.s.d. MAD/c.s.d. Mean c.s.d. (Å)
IAM −0.121 0.122 −5.12 5.15 0.046
IAM_NoMoRe −0.119 0.120 −3.98 4.00 0.039
IAM_SHADE3 −0.127 0.127 −4.93 4.95 0.031
IAM_0_HADPs −0.134 0.135 −5.51 5.54 0.030
HAR 0.004 0.027 0.08 0.85 0.034
HAR_NoMoRe 0.005 0.032 0.03 0.89 0.038
HAR_NoMoRe_1 0.005 0.028 0.04 0.83 0.037
HAR_SHADE3 0.001 0.031 −0.01 0.92 0.035
HAR_SHADE3_1 0.000 0.035 −0.02 0.97 0.036
HAR_0_HADPs 0.003 0.042 0.00 1.47 0.030
Optimized −0.001 0.014 −0.19 1.01 0.016

Table 7
MD, MAD, MD/c.s.d. and MAD/c.s.d. values calculated between the neutron and the X-ray/optimized bond lengths averaged for the TM—H bonds in all the structures

Since there are only 15 TM—H bond lengths in total, no statistical tests were performed on the averaged values.

Method MD (Å) MAD (Å) MD/c.s.d. MAD/c.s.d. Mean c.s.d. (Å)
IAM −0.028 0.046 −1.24 1.97 0.037
IAM_NoMoRe −0.028 0.039 −1.25 1.65 0.039
IAM_SHADE3 −0.030 0.039 −1.44 1.76 0.034
IAM_0_HADPs −0.023 0.038 −1.31 1.71 0.028
HAR 0.031 0.036 0.62 0.97 0.033
HAR_NoMoRe 0.025 0.043 0.29 1.31 0.038
HAR_NoMoRe_1 0.026 0.042 0.37 1.29 0.038
HAR_SHADE3 0.026 0.042 0.32 1.32 0.036
HAR_SHADE3_1 0.030 0.045 0.38 1.26 0.038
HAR_0_HADPs 0.032 0.052 0.55 1.64 0.031
Optimized −0.005 0.017 −0.04 1.56 0.012
[Figure 6]
Figure 6
MAD between the X-ray/geometry-optimized and neutron values of the X—H and TM—H bond lengths with the c.s.d. averaged for the X—H/TM—H bonds in each structure as error bars. The X-ray values were obtained with various refinement methods. The structures are ordered according to their position in the X-ray (HAR)–neutron data- and refinement-quality ranking from best to worst.

The results indicate that tweaking HAR using more sophisticated methods for describing hydrogen thermal vibrations has minimal impact on the X—H and TM—H bond lengths in the investigated cases. As shown in Fig. 6[link], MAD between the HAR and the neutron bond lengths is fairly consistent across different hydrogen ADP estimation methods. Even setting hydrogen ADPs to 0 (IAM_0_HADPs/HAR_0_HADPs) does not significantly alter the X—H or TM—H bond lengths compared with conventional IAM/HAR, although some variability exists depending on the structure. MAD plots in Fig. 6[link] show that in the case of X—H bond lengths, the IAM values of MAD are consistently higher than 0.1 Å, with little variability related to different methods of estimating hydrogen ADPs. HAR generally yields lower MAD values for X—H bond lengths compared with IAM. Moreover, MAD obtained with HAR is the lowest for the structures from the top of the ranking and tends to increase with decreasing quality. For KCPTCR, pruning reflections has a minor effect on MAD for both HAR and IAM refinements.

For the TM—H bond lengths obtained with various HAR versions, it can also be observed that MAD tends to increase with lower position in the ranking and for some structures MAD is slightly higher than for the X—H bond lengths. Surprisingly, IAM yields lower MAD values for TM—H bond lengths compared with X—H bond lengths and, on average, MAD values are only slightly higher than those for HAR. For KCPTCR_std and KCPTCR_max, MAD is relatively consistent across various IAM and HAR types, although conventional HAR provides the best agreement of Cr—H bond lengths with the neutron structure.

The findings summarized in Tables 6[link] and 7[link] confirm the observations in the previous paragraph. All types of IAM, irrespective of the method of hydrogen thermal motion treatment, underestimate the X—H bond lengths in the investigated structures by on average 0.012–0.013 Å. In the case where all the variants of HAR and the geometry-optimized structure, MD is very close to 0. However, for HAR and HAR_NoMoRe(_1), MD is slightly different from 0 but still statistically significant. MAD values in these cases are significantly different from 0 but much lower compared with IAM. Geometry optimization results in the lowest MAD (0.014 Å). MAD is twice as high for HAR (0.027 Å) and HAR_NoMoRe_1 (0.028 Å). MAD increases slightly for HAR_NoMoRe (0.032 Å) and HAR_SHADE3(_1) (0.031 Å (0.035 Å), and finally for HAR_0_HADPs (0.042 Å) it is still much lower than in the case of IAM. The differences in MAD for X—H bond lengths for various types of IAM are quite small and the highest MAD is attained for IAM_0_HADPs.

Unfortunately, for TM—H bond lengths, statistical testing is impossible due to the small sample size of only 15 bonds. In this case, geometry optimization, which closely aligns with neutron values, slightly underestimates the bond lengths (MD = −0.005 Å and MAD = 0.017 Å). IAM tends to underestimate the TM—H bond lengths (MD ranging from −0.023 to −0.030 Å), resulting in MAD values of 0.038–0.046 Å, similar to what HAR achieves for X—H bond lengths. HAR, conversely, generally overestimates TM—H bond lengths (MD equal to 0.025–0.032 Å). The divergence of HAR values from neutron values, as estimated by MAD, has a similar range to IAM. However, in HAR the lowest MAD is obtained with standard HAR (0.036 Å) and the highest with HAR_0_HADPs (0.052 Å). In the case of IAM, IAM_0_HADPs results in the lowest MAD (0.038 Å) and standard IAM yields the highest MAD (0.046 Å). In summary, for the studied compounds, HAR performs slightly worse for TM—H bond lengths compared with the general case. The IAM performance for TM—H bond lengths is slightly worse than that of HAR and it appears to improve after using SHADE3 or NoMoRe, unlike the HAR performance for TM—H bond lengths. These conclusions are based on quite a small set of structures and the good agreement between the neutron and IAM TM—H bond lengths could be a coincidence. The role of high data quality, crucial for determining hydrogen positions with HAR in typical X—H bonds, seems to be even more critical for TM—H bond lengths, whereas this might not be an issue for IAM, perhaps accidentally.

3. Conclusions

This study aimed to combine HAR with sophisticated methods of estimating anisotropic thermal motions of hydrogen atoms – NoMoRe and SHADE3 – for seven X-ray datasets of TM/metalloid hydrides, with neutron structures serving as benchmarks. The primary objective was to investigate whether a more accurate estimation of hydrogen ADPs could enhance the positions of hydrogen atoms obtained from HAR, especially near heavy metals. The second goal was to assess the discrepancies between the thermal ellipsoids of hydrogen atoms obtained with various methods. Anisotropic HAR was feasible for only four structures. Neutron data were collected at the same temperature as the X-ray data for just two structures, one of which allowed anisotropic HAR. For one structure, a high-resolution X-ray dataset was collected and the neutron experiment was performed at a similar temperature, which enabled an examination of how data resolution affected atomic positions and thermal parameters.

The first observation regarding hydrogen ADPs is that, compared with SHADE3, NoMoRe yields hydrogen thermal ellipsoids in better agreement with those refined by HAR and this agreement correlates with the data-refinement quality ranking of the structure. Similarly, when comparing neutron hydrogen ADPs to those estimated by NoMoRe or SHADE3, the former results in smaller discrepancies with neutron ellipsoids and the corresponding S12 values are strongly dependent on the specific structure. In comparisons between the neutron and the HAR hydrogen ADPs made for the only two structures for which it was feasible (GOJNIF and KCPTCR), a high discrepancy was also observed. For KCPTCR (standard resolution) averaged S12 was slightly lower than for KCPTCR (high resolution) and significantly lower than for GOJNIF. Nonetheless, considering the high estimated error values of averaged S12, these differences fall within the margin of error. As expected, NoMoRe yields hydrogen ADPs with the best agreement with neutron hydrogen ADPs, SHADE3 lags slightly behind, and HAR results in the most divergent hydrogen ADPs. Non-hydrogen ADPs are almost unaffected by hydrogen ADPs, even when those values are obviously erroneous (e.g. fixed at 0). Hydrogen ADPs obtained from HAR with high-resolution X-ray data are slightly more divergent from neutron hydrogen ADPs than in the case of standard-resolution X-ray data. It can be concluded that the information used by HAR to model hydrogen ADPs is mostly low-resolution data, with high-resolution data primarily introducing noise. The effect of data resolution on non-hydrogen atom ADPs differs for HAR and IAM. In HAR, using the high-resolution part of the data makes non-hydrogen ADPs only slightly more similar to neutron ones, whereas in IAM, it makes non-hydrogen ADPs much more similar to neutron ones. It appears that high-resolution X-ray data are needed to improve the description of thermal motion of non-hydrogen atoms with IAM, while standard resolution suffices for HAR.

The second issue addressed in this study was the impact of different methods of describing hydrogen thermal vibrations of X—H and, in particular, TM—H bond lengths. While there was some variability in X—H/TM—H bond lengths due to different hydrogen thermal motion estimation methods for individual structures, on average, the method of obtaining ADPs did not significantly influence hydrogen atom positions, even when the ADPs were set to 0 in IAM or HAR. In the case of IAM, the resulting average X—H bond lengths were very similar for all seven structures and they were underestimated by on average 0.121–0.134 Å. For HAR, discrepancies with mean neutron X—H bond lengths tended to increase with deteriorating position of the structure in the joint data-refinement quality X-ray–neutron ranking. HAR performed much better than IAM for X—H bond lengths, with discrepancies from neutron bond lengths varying depending on the hydrogen thermal motion treatment method, ranging from the lowest MAD in conventional HAR (0.027 Å) to slightly higher MAD in HAR_0_HADPs (0.042 Å). Surprisingly, IAM performed better for TM—H bond lengths, with average discrepancies from neutron bond lengths ranging from 0.038 Å (IAM_0_HADPs) to 0.046 Å (IAM). The IAM performance in terms of TM—H bond lengths was notably better for the structures with the worst position in the data and refinement quality ranking. In comparison, HAR yielded similar levels of discrepancy with neutron TM—H bonds as IAM, with MAD ranging from 0.036 Å (HAR) to 0.052 Å (HAR_0_HADPs). Note that geometry optimization resulted in high agreement with neutron positions, both for all X—H bond lengths (MAD = 0.014 Å) and for specifically TM—H bond lengths (MAD = 0.017 Å).

In conclusion, applying more precise and much more costly methods to describe hydrogen thermal motions did not improve hydrogen position determination in HAR. On the contrary, conventional HAR used to refine both hydrogen positions and thermal motions slightly outperformed HAR during which hydrogen thermal motions were fixed at the values estimated by sophisticated techniques such as NoMoRe and SHADE3. Nevertheless, this scientific problem certainly deserves more in-depth investigation.

Supporting information


Computing details top

(GOJNIF_HAR_0_HADPs) top
Crystal data top
C39H62InN4NiP3Dx = 1.415 Mg m3
Mr = 853.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9537 reflections
a = 12.2127 (4) Åθ = 2.3–36.4°
b = 14.5402 (5) ŵ = 1.20 mm1
c = 22.5601 (8) ÅT = 100 K
V = 4006.1 (2) Å3Block, gold
Z = 40.14 × 0.08 × 0.06 mm
F(000) = 105.781
Data collection top
Bruker Photon-II CMOS
diffractometer
18741 reflections with I 2u(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
SADABS. R.Blessing, 1995
θmax = 36.4°, θmin = 2.3°
Tmin = 0.701, Tmax = 0.747h = 2020
237431 measured reflectionsk = 2424
19473 independent reflectionsl = 3737
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullOnly H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.021 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max = 0.001
S = 0.69Δρmax = 0.32 e Å3
19473 reflectionsΔρmin = 0.99 e Å3
619 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
0 restraintsAbsolute structure parameter: 0.004 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.755794 (12)0.598667 (10)0.856158 (7)0.00973 (3)
H1A0.7244 (17)0.5612 (15)0.9258 (9)0.000000
H1B0.7516 (17)0.6221 (15)0.9292 (9)0.000000
In10.798245 (6)0.580828 (5)0.749329 (3)0.00865 (2)
P10.91843 (2)0.52226 (2)0.864349 (13)0.00966 (5)
P20.59903 (2)0.52856 (2)0.829183 (13)0.00973 (5)
P30.75364 (3)0.75010 (2)0.835663 (12)0.00939 (4)
N10.96175 (7)0.53390 (7)0.74724 (5)0.01104 (14)
N20.67674 (9)0.48674 (7)0.72031 (4)0.01165 (16)
N30.78418 (9)0.71637 (7)0.71622 (4)0.01086 (15)
N40.83414 (8)0.56330 (7)0.64680 (4)0.00916 (14)
C10.95349 (9)0.57155 (7)0.64338 (5)0.00953 (15)
C21.00508 (10)0.59713 (9)0.59111 (5)0.01339 (18)
H2A0.9635 (13)0.6143 (11)0.5554 (7)0.000000
C31.11903 (11)0.60875 (9)0.58826 (6)0.0150 (2)
H3A1.1648 (15)0.6210 (13)0.5471 (7)0.000000
C41.18058 (10)0.59547 (9)0.63983 (6)0.01458 (19)
H4A1.2641 (13)0.6076 (11)0.6377 (7)0.000000
C51.12988 (10)0.57046 (9)0.69278 (5)0.01301 (18)
H5A1.1850 (16)0.5651 (13)0.7349 (8)0.000000
C61.01529 (10)0.55737 (8)0.69636 (5)0.01010 (17)
C71.01955 (10)0.53667 (9)0.80305 (5)0.01191 (18)
H7A1.0641 (13)0.5966 (11)0.8137 (7)0.000000
H7B1.0918 (15)0.4849 (12)0.8011 (7)0.000000
C80.99537 (11)0.56222 (9)0.93123 (5)0.01450 (19)
H8A0.9835 (15)0.6403 (13)0.9306 (8)0.000000
C90.91100 (10)0.39466 (8)0.87154 (6)0.01448 (19)
H9A0.8490 (14)0.3821 (13)0.9077 (7)0.000000
C101.12048 (12)0.55060 (12)0.93058 (7)0.0227 (3)
H10A1.1499 (16)0.4685 (14)0.9324 (8)0.000000
H10B1.1541 (13)0.5837 (11)0.8967 (7)0.000000
H10C1.1561 (16)0.5756 (14)0.9845 (9)0.000000
C110.94557 (16)0.52140 (13)0.98765 (6)0.0265 (3)
H11A1.0043 (14)0.5499 (13)1.0236 (8)0.000000
H11B0.8601 (13)0.5341 (12)0.9944 (7)0.000000
H11C0.9654 (15)0.4443 (12)0.9891 (7)0.000000
C120.86437 (13)0.35251 (9)0.81442 (6)0.0191 (2)
H12A0.8582 (14)0.2802 (12)0.8228 (7)0.000000
H12B0.7822 (14)0.3920 (13)0.8025 (8)0.000000
H12C0.9247 (14)0.3579 (12)0.7807 (7)0.000000
C131.01669 (13)0.34492 (11)0.88741 (8)0.0242 (3)
H13A1.0162 (14)0.2730 (12)0.8987 (7)0.000000
H13B1.0889 (14)0.3649 (12)0.8618 (7)0.000000
H13C1.0588 (15)0.3643 (12)0.9270 (7)0.000000
C140.78942 (9)0.47291 (7)0.63335 (5)0.01020 (16)
C150.82593 (10)0.42283 (9)0.58486 (5)0.01245 (17)
H15A0.8935 (15)0.4560 (13)0.5554 (8)0.000000
C160.78534 (11)0.33508 (9)0.57252 (6)0.0157 (2)
H16A0.8118 (14)0.2971 (12)0.5337 (7)0.000000
C170.70742 (11)0.29751 (9)0.61056 (6)0.0162 (2)
H17A0.6707 (15)0.2273 (13)0.5969 (8)0.000000
C180.67030 (11)0.34629 (9)0.65972 (6)0.01473 (19)
H18A0.6169 (14)0.3114 (12)0.6898 (7)0.000000
C190.70933 (9)0.43559 (8)0.67272 (5)0.01066 (16)
C200.60332 (10)0.44844 (8)0.76429 (5)0.01226 (17)
H20A0.6198 (15)0.3760 (12)0.7836 (8)0.000000
H20B0.5220 (13)0.4408 (12)0.7434 (7)0.000000
C210.53642 (10)0.45616 (9)0.88806 (5)0.01363 (19)
H21A0.4654 (14)0.4161 (13)0.8693 (7)0.000000
C220.48067 (9)0.60412 (9)0.80772 (5)0.01273 (18)
H22A0.4859 (14)0.6595 (12)0.8402 (7)0.000000
C230.61419 (12)0.38126 (11)0.91006 (6)0.0204 (2)
H23A0.5666 (15)0.3404 (12)0.9426 (7)0.000000
H23B0.6422 (14)0.3323 (12)0.8780 (7)0.000000
H23C0.6926 (16)0.4200 (13)0.9360 (8)0.000000
C240.49899 (12)0.51677 (10)0.93996 (6)0.0187 (2)
H24A0.4354 (16)0.5793 (14)0.9243 (8)0.000000
H24B0.4538 (14)0.4749 (12)0.9719 (7)0.000000
H24C0.5624 (14)0.5525 (12)0.9646 (7)0.000000
C250.49936 (11)0.64734 (10)0.74673 (7)0.01745 (19)
H25A0.4321 (14)0.6971 (12)0.7366 (7)0.000000
H25B0.5753 (13)0.6754 (11)0.7367 (7)0.000000
H25C0.4997 (14)0.5910 (12)0.7135 (7)0.000000
C260.36782 (11)0.55810 (11)0.80854 (6)0.0176 (2)
H26A0.3036 (14)0.6088 (12)0.7971 (7)0.000000
H26B0.3681 (14)0.5024 (11)0.7801 (7)0.000000
H26C0.3400 (15)0.5180 (13)0.8480 (7)0.000000
C270.77569 (10)0.64133 (8)0.62084 (5)0.01049 (17)
C280.74244 (12)0.64009 (8)0.56206 (5)0.01472 (19)
H28A0.7512 (16)0.5693 (13)0.5388 (8)0.000000
C290.69219 (13)0.71640 (10)0.53612 (6)0.0185 (2)
H29A0.6685 (13)0.7124 (11)0.4932 (7)0.000000
C300.67558 (12)0.79459 (9)0.57063 (6)0.0171 (2)
H30A0.6348 (16)0.8605 (14)0.5438 (8)0.000000
C310.70545 (11)0.79585 (8)0.63009 (5)0.01365 (18)
H31A0.6886 (13)0.8510 (11)0.6548 (7)0.000000
C320.75548 (10)0.71935 (8)0.65747 (5)0.01058 (16)
C330.74788 (10)0.78795 (7)0.75560 (5)0.01177 (16)
H33A0.6602 (14)0.8074 (12)0.7473 (8)0.000000
H33B0.7982 (12)0.8508 (12)0.7535 (7)0.000000
C340.62768 (10)0.80860 (8)0.86330 (5)0.01212 (17)
H34A0.5633 (14)0.7822 (12)0.8355 (7)0.000000
C350.86864 (10)0.82268 (8)0.86211 (6)0.01360 (18)
H35A0.8511 (13)0.8906 (12)0.8482 (7)0.000000
C360.63050 (11)0.91398 (9)0.86001 (6)0.0164 (2)
H36A0.6580 (13)0.9363 (11)0.8210 (7)0.000000
H36B0.5464 (14)0.9348 (12)0.8686 (7)0.000000
H36C0.6793 (16)0.9424 (13)0.9009 (8)0.000000
C370.59237 (12)0.77684 (10)0.92545 (6)0.0182 (2)
H37A0.5083 (14)0.8042 (13)0.9327 (8)0.000000
H37B0.6123 (13)0.7113 (11)0.9358 (7)0.000000
H37C0.6489 (13)0.8014 (12)0.9555 (7)0.000000
C380.97438 (11)0.79003 (10)0.83210 (6)0.0173 (2)
H38A1.0317 (14)0.8407 (11)0.8344 (7)0.000000
H38B0.9913 (14)0.7232 (12)0.8532 (7)0.000000
H38C0.9638 (15)0.7759 (13)0.7812 (8)0.000000
C390.88000 (12)0.82434 (10)0.92962 (6)0.0184 (2)
H39A0.9585 (16)0.8568 (13)0.9503 (8)0.000000
H39B0.8149 (15)0.8679 (12)0.9514 (7)0.000000
H39C0.8751 (15)0.7527 (13)0.9477 (7)0.000000
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.00899 (5)0.00842 (5)0.01178 (6)0.00032 (4)0.00040 (4)0.00001 (4)
H1A0.0000000.0000000.0000000.0000000.0000000.000000
H1B0.0000000.0000000.0000000.0000000.0000000.000000
In10.00886 (3)0.00814 (3)0.00895 (3)0.000085 (18)0.00013 (2)0.00011 (2)
P10.01033 (11)0.00983 (11)0.00884 (11)0.00072 (9)0.00064 (8)0.00055 (8)
P20.00907 (10)0.01103 (11)0.00910 (10)0.00187 (9)0.00045 (8)0.00029 (9)
P30.01131 (11)0.00787 (10)0.00898 (10)0.00032 (9)0.00060 (9)0.00082 (8)
N10.0097 (3)0.0139 (4)0.0095 (3)0.0009 (3)0.0002 (3)0.0013 (3)
N20.0119 (4)0.0124 (4)0.0106 (4)0.0020 (3)0.0015 (3)0.0026 (3)
N30.0148 (4)0.0091 (3)0.0087 (3)0.0014 (3)0.0004 (3)0.0002 (3)
N40.0110 (3)0.0092 (3)0.0073 (3)0.0009 (3)0.0012 (3)0.0000 (3)
C10.0098 (4)0.0096 (4)0.0093 (4)0.0005 (3)0.0020 (3)0.0001 (3)
C20.0149 (4)0.0141 (4)0.0111 (4)0.0001 (4)0.0033 (3)0.0000 (3)
H2A0.0000000.0000000.0000000.0000000.0000000.000000
C30.0151 (5)0.0162 (5)0.0137 (5)0.0007 (4)0.0039 (4)0.0009 (4)
H3A0.0000000.0000000.0000000.0000000.0000000.000000
C40.0117 (4)0.0157 (4)0.0164 (5)0.0010 (4)0.0035 (4)0.0012 (4)
H4A0.0000000.0000000.0000000.0000000.0000000.000000
C50.0105 (4)0.0157 (5)0.0128 (4)0.0001 (3)0.0004 (3)0.0008 (4)
H5A0.0000000.0000000.0000000.0000000.0000000.000000
C60.0098 (4)0.0110 (4)0.0094 (4)0.0006 (3)0.0014 (3)0.0004 (3)
C70.0111 (4)0.0142 (4)0.0105 (4)0.0007 (4)0.0001 (3)0.0001 (3)
H7A0.0000000.0000000.0000000.0000000.0000000.000000
H7B0.0000000.0000000.0000000.0000000.0000000.000000
C80.0157 (5)0.0167 (5)0.0112 (4)0.0010 (4)0.0023 (4)0.0005 (4)
H8A0.0000000.0000000.0000000.0000000.0000000.000000
C90.0161 (5)0.0111 (4)0.0163 (5)0.0015 (4)0.0003 (4)0.0027 (4)
H9A0.0000000.0000000.0000000.0000000.0000000.000000
C100.0163 (5)0.0298 (7)0.0218 (6)0.0005 (5)0.0075 (5)0.0035 (5)
H10A0.0000000.0000000.0000000.0000000.0000000.000000
H10B0.0000000.0000000.0000000.0000000.0000000.000000
H10C0.0000000.0000000.0000000.0000000.0000000.000000
C110.0339 (8)0.0351 (8)0.0105 (5)0.0097 (7)0.0003 (5)0.0009 (5)
H11A0.0000000.0000000.0000000.0000000.0000000.000000
H11B0.0000000.0000000.0000000.0000000.0000000.000000
H11C0.0000000.0000000.0000000.0000000.0000000.000000
C120.0257 (6)0.0119 (5)0.0198 (5)0.0001 (4)0.0019 (5)0.0027 (4)
H12A0.0000000.0000000.0000000.0000000.0000000.000000
H12B0.0000000.0000000.0000000.0000000.0000000.000000
H12C0.0000000.0000000.0000000.0000000.0000000.000000
C130.0201 (6)0.0152 (5)0.0372 (8)0.0050 (5)0.0055 (6)0.0058 (5)
H13A0.0000000.0000000.0000000.0000000.0000000.000000
H13B0.0000000.0000000.0000000.0000000.0000000.000000
H13C0.0000000.0000000.0000000.0000000.0000000.000000
C140.0130 (4)0.0088 (4)0.0088 (4)0.0017 (3)0.0002 (3)0.0013 (3)
C150.0153 (4)0.0126 (4)0.0095 (4)0.0001 (4)0.0007 (3)0.0017 (3)
H15A0.0000000.0000000.0000000.0000000.0000000.000000
C160.0206 (5)0.0130 (4)0.0135 (4)0.0010 (4)0.0012 (4)0.0055 (4)
H16A0.0000000.0000000.0000000.0000000.0000000.000000
C170.0182 (5)0.0131 (4)0.0173 (5)0.0033 (4)0.0001 (4)0.0049 (4)
H17A0.0000000.0000000.0000000.0000000.0000000.000000
C180.0146 (4)0.0120 (4)0.0175 (5)0.0027 (4)0.0009 (4)0.0039 (4)
H18A0.0000000.0000000.0000000.0000000.0000000.000000
C190.0109 (4)0.0111 (4)0.0100 (4)0.0006 (3)0.0001 (3)0.0025 (3)
C200.0108 (4)0.0135 (4)0.0125 (4)0.0034 (3)0.0018 (3)0.0016 (3)
H20A0.0000000.0000000.0000000.0000000.0000000.000000
H20B0.0000000.0000000.0000000.0000000.0000000.000000
C210.0135 (4)0.0164 (5)0.0110 (4)0.0036 (4)0.0009 (3)0.0011 (4)
H21A0.0000000.0000000.0000000.0000000.0000000.000000
C220.0099 (4)0.0158 (4)0.0125 (4)0.0003 (4)0.0009 (3)0.0022 (4)
H22A0.0000000.0000000.0000000.0000000.0000000.000000
C230.0214 (6)0.0217 (6)0.0180 (5)0.0003 (5)0.0031 (4)0.0066 (4)
H23A0.0000000.0000000.0000000.0000000.0000000.000000
H23B0.0000000.0000000.0000000.0000000.0000000.000000
H23C0.0000000.0000000.0000000.0000000.0000000.000000
C240.0247 (6)0.0215 (6)0.0099 (4)0.0056 (5)0.0026 (4)0.0014 (4)
H24A0.0000000.0000000.0000000.0000000.0000000.000000
H24B0.0000000.0000000.0000000.0000000.0000000.000000
H24C0.0000000.0000000.0000000.0000000.0000000.000000
C250.0170 (5)0.0196 (5)0.0157 (5)0.0026 (4)0.0013 (4)0.0033 (5)
H25A0.0000000.0000000.0000000.0000000.0000000.000000
H25B0.0000000.0000000.0000000.0000000.0000000.000000
H25C0.0000000.0000000.0000000.0000000.0000000.000000
C260.0108 (4)0.0221 (6)0.0198 (5)0.0021 (4)0.0013 (4)0.0028 (4)
H26A0.0000000.0000000.0000000.0000000.0000000.000000
H26B0.0000000.0000000.0000000.0000000.0000000.000000
H26C0.0000000.0000000.0000000.0000000.0000000.000000
C270.0149 (4)0.0092 (4)0.0074 (4)0.0020 (3)0.0006 (3)0.0004 (3)
C280.0214 (5)0.0128 (4)0.0100 (4)0.0038 (4)0.0025 (4)0.0014 (3)
H28A0.0000000.0000000.0000000.0000000.0000000.000000
C290.0274 (6)0.0175 (5)0.0105 (4)0.0084 (5)0.0061 (4)0.0003 (4)
H29A0.0000000.0000000.0000000.0000000.0000000.000000
C300.0241 (6)0.0160 (5)0.0111 (4)0.0084 (4)0.0032 (4)0.0009 (4)
H30A0.0000000.0000000.0000000.0000000.0000000.000000
C310.0177 (5)0.0120 (4)0.0112 (4)0.0044 (4)0.0005 (4)0.0006 (3)
H31A0.0000000.0000000.0000000.0000000.0000000.000000
C320.0125 (4)0.0093 (4)0.0099 (4)0.0014 (3)0.0009 (3)0.0003 (3)
C330.0163 (4)0.0086 (3)0.0104 (4)0.0013 (3)0.0004 (4)0.0006 (3)
H33A0.0000000.0000000.0000000.0000000.0000000.000000
H33B0.0000000.0000000.0000000.0000000.0000000.000000
C340.0146 (4)0.0114 (4)0.0104 (4)0.0010 (3)0.0002 (3)0.0008 (3)
H34A0.0000000.0000000.0000000.0000000.0000000.000000
C350.0156 (4)0.0108 (4)0.0144 (5)0.0019 (4)0.0005 (4)0.0021 (4)
H35A0.0000000.0000000.0000000.0000000.0000000.000000
C360.0202 (5)0.0120 (4)0.0169 (5)0.0029 (4)0.0012 (4)0.0010 (4)
H36A0.0000000.0000000.0000000.0000000.0000000.000000
H36B0.0000000.0000000.0000000.0000000.0000000.000000
H36C0.0000000.0000000.0000000.0000000.0000000.000000
C370.0242 (6)0.0168 (5)0.0137 (5)0.0008 (5)0.0043 (4)0.0010 (4)
H37A0.0000000.0000000.0000000.0000000.0000000.000000
H37B0.0000000.0000000.0000000.0000000.0000000.000000
H37C0.0000000.0000000.0000000.0000000.0000000.000000
C380.0160 (5)0.0192 (5)0.0167 (5)0.0046 (4)0.0015 (4)0.0034 (4)
H38A0.0000000.0000000.0000000.0000000.0000000.000000
H38B0.0000000.0000000.0000000.0000000.0000000.000000
H38C0.0000000.0000000.0000000.0000000.0000000.000000
C390.0194 (5)0.0207 (5)0.0151 (5)0.0033 (5)0.0032 (4)0.0041 (4)
H39A0.0000000.0000000.0000000.0000000.0000000.000000
H39B0.0000000.0000000.0000000.0000000.0000000.000000
H39C0.0000000.0000000.0000000.0000000.0000000.000000
Geometric parameters (Å, º) top
Ni1—H1A1.71 (2)C14—C191.4282 (16)
Ni1—H1B1.68 (2)C15—H15A1.164 (18)
Ni1—In12.4788 (2)C15—C161.3968 (18)
Ni1—P12.2834 (3)C16—H16A1.086 (17)
Ni1—P22.2527 (3)C16—C171.3931 (19)
Ni1—P32.2501 (3)C17—H17A1.156 (18)
H1A—H1B0.95 (3)C17—C181.3922 (18)
In1—N12.1108 (9)C18—H18A1.070 (17)
In1—N22.1218 (10)C18—C191.4139 (17)
In1—N32.1146 (10)C20—H20A1.157 (18)
In1—N42.3681 (10)C20—H20B1.105 (16)
P1—C71.8658 (12)C21—H21A1.128 (18)
P1—C81.8702 (13)C21—C231.528 (2)
P1—C91.8645 (13)C21—C241.5353 (19)
P2—C201.8716 (12)C22—H22A1.090 (17)
P2—C211.8593 (12)C22—C251.5299 (19)
P2—C221.8791 (12)C22—C261.5322 (18)
P3—C331.8894 (12)C23—H23A1.110 (17)
P3—C341.8651 (12)C23—H23B1.070 (17)
P3—C351.8553 (12)C23—H23C1.256 (19)
N1—C61.3644 (15)C24—H24A1.25 (2)
N1—C71.4440 (16)C24—H24B1.093 (17)
N2—C191.3655 (15)C24—H24C1.085 (17)
N2—C201.4487 (15)C25—H25A1.118 (17)
N3—C321.3718 (14)C25—H25B1.038 (16)
N3—C331.4385 (15)C25—H25C1.110 (17)
N4—C11.4645 (15)C26—H26A1.107 (17)
N4—C141.4551 (15)C26—H26B1.033 (16)
N4—C271.4627 (14)C26—H26C1.117 (17)
C1—C21.3879 (16)C27—C281.3871 (16)
C1—C61.4284 (16)C27—C321.4250 (16)
C2—H2A0.984 (15)C28—H28A1.161 (18)
C2—C31.4034 (18)C28—C291.3965 (18)
C3—H3A1.098 (17)C29—H29A1.013 (16)
C3—C41.3984 (18)C29—C301.3928 (19)
C4—H4A1.036 (16)C30—H30A1.238 (19)
C4—C51.3938 (17)C30—C311.3903 (18)
C5—H5A1.168 (18)C31—H31A0.998 (16)
C5—C61.4147 (17)C31—C321.4113 (16)
C7—H7A1.056 (16)C33—H33A1.124 (17)
C7—H7B1.161 (18)C33—H33B1.102 (17)
C8—H8A1.144 (18)C34—H34A1.077 (16)
C8—C101.537 (2)C34—C361.5345 (18)
C8—C111.530 (2)C34—C371.5380 (18)
C9—H9A1.128 (17)C35—H35A1.059 (17)
C9—C121.5365 (19)C35—C381.5335 (19)
C9—C131.5223 (19)C35—C391.5296 (18)
C10—H10A1.25 (2)C36—H36A0.997 (16)
C10—H10B0.993 (15)C36—H36B1.088 (17)
C10—H10C1.34 (2)C36—H36C1.174 (18)
C11—H11A1.160 (18)C37—H37A1.113 (17)
C11—H11B1.071 (16)C37—H37B1.011 (16)
C11—H11C1.148 (18)C37—H37C1.031 (16)
C12—H12A1.072 (18)C38—H38A1.018 (17)
C12—H12B1.187 (18)C38—H38B1.101 (17)
C12—H12C1.061 (16)C38—H38C1.173 (18)
C13—H13A1.076 (18)C39—H39A1.166 (19)
C13—H13B1.094 (17)C39—H39B1.129 (18)
C13—H13C1.068 (17)C39—H39C1.120 (18)
C14—C151.3877 (16)
H1B—Ni1—H1A32.5 (9)C15—C14—N4121.18 (10)
In1—Ni1—H1A155.3 (7)C19—C14—N4118.08 (9)
In1—Ni1—H1B168.3 (7)C19—C14—C15120.71 (10)
P1—Ni1—H1A88.0 (7)H15A—C15—C14117.4 (9)
P1—Ni1—H1B92.6 (7)C16—C15—C14121.50 (11)
P1—Ni1—In181.131 (9)C16—C15—H15A121.1 (9)
P2—Ni1—H1A85.0 (7)H16A—C16—C15121.4 (9)
P2—Ni1—H1B109.3 (7)C17—C16—C15118.54 (11)
P2—Ni1—In182.400 (9)C17—C16—H16A120.1 (9)
P2—Ni1—P1122.750 (13)H17A—C17—C16116.6 (9)
P3—Ni1—H1A119.9 (7)C18—C17—C16120.89 (11)
P3—Ni1—H1B90.2 (7)C18—C17—H17A122.3 (9)
P3—Ni1—In184.552 (9)H18A—C18—C17117.6 (9)
P3—Ni1—P1120.196 (13)C19—C18—C17121.55 (12)
P3—Ni1—P2112.170 (13)C19—C18—H18A120.6 (9)
H1B—H1A—Ni172.5 (19)C14—C19—N2118.79 (10)
H1A—H1B—Ni175.0 (19)C18—C19—N2124.40 (11)
N1—In1—Ni1104.68 (3)C18—C19—C14116.80 (10)
N2—In1—Ni1102.78 (3)N2—C20—P2108.29 (8)
N2—In1—N1116.51 (4)H20A—C20—P2106.1 (9)
N3—In1—Ni1103.23 (3)H20A—C20—N2120.0 (9)
N3—In1—N1111.73 (4)H20B—C20—P2111.7 (9)
N3—In1—N2115.79 (4)H20B—C20—N2107.7 (9)
N4—In1—Ni1178.59 (2)H20B—C20—H20A103.0 (13)
N4—In1—N176.60 (4)H21A—C21—P2109.9 (9)
N4—In1—N276.04 (4)C23—C21—P2112.34 (9)
N4—In1—N376.72 (3)C23—C21—H21A103.5 (9)
C7—P1—Ni1117.46 (4)C24—C21—P2110.01 (9)
C8—P1—Ni1110.56 (4)C24—C21—H21A110.7 (9)
C8—P1—C7103.33 (6)C24—C21—C23110.27 (11)
C9—P1—Ni1116.67 (4)H22A—C22—P2102.4 (9)
C9—P1—C7102.03 (6)C25—C22—P2110.93 (8)
C9—P1—C8105.27 (6)C25—C22—H22A107.0 (9)
C20—P2—Ni1117.98 (4)C26—C22—P2115.69 (10)
C21—P2—Ni1114.38 (4)C26—C22—H22A111.5 (9)
C21—P2—C20102.58 (5)C26—C22—C25108.93 (10)
C22—P2—Ni1117.31 (4)H23A—C23—C21105.8 (9)
C22—P2—C20100.60 (6)H23B—C23—C21117.0 (9)
C22—P2—C21101.46 (6)H23B—C23—H23A105.0 (13)
C33—P3—Ni1118.81 (3)H23C—C23—C21107.8 (9)
C34—P3—Ni1112.78 (4)H23C—C23—H23A109.3 (12)
C34—P3—C3398.98 (5)H23C—C23—H23B111.6 (13)
C35—P3—Ni1118.80 (4)H24A—C24—C21112.8 (9)
C35—P3—C3399.78 (6)H24B—C24—C21109.5 (9)
C35—P3—C34104.92 (5)H24B—C24—H24A106.1 (13)
C6—N1—In1113.03 (8)H24C—C24—C21116.9 (9)
C7—N1—In1115.72 (7)H24C—C24—H24A103.9 (13)
C7—N1—C6119.50 (9)H24C—C24—H24B106.8 (12)
C19—N2—In1112.95 (8)H25A—C25—C22109.9 (9)
C20—N2—In1117.99 (7)H25B—C25—C22119.4 (9)
C20—N2—C19120.64 (10)H25B—C25—H25A110.9 (13)
C32—N3—In1113.05 (7)H25C—C25—C22107.7 (9)
C33—N3—In1118.76 (7)H25C—C25—H25A110.0 (12)
C33—N3—C32119.69 (10)H25C—C25—H25B98.1 (13)
C1—N4—In1103.11 (7)H26A—C26—C22110.1 (9)
C14—N4—In1103.38 (6)H26B—C26—C22109.4 (9)
C14—N4—C1115.89 (9)H26B—C26—H26A112.3 (12)
C27—N4—In1102.54 (6)H26C—C26—C22120.8 (9)
C27—N4—C1113.65 (9)H26C—C26—H26A108.5 (13)
C27—N4—C14115.72 (9)H26C—C26—H26B94.9 (13)
C2—C1—N4121.23 (10)C28—C27—N4121.04 (10)
C6—C1—N4118.04 (10)C32—C27—N4118.03 (9)
C6—C1—C2120.65 (10)C32—C27—C28120.93 (10)
H2A—C2—C1121.9 (9)H28A—C28—C27114.7 (9)
C3—C2—C1121.42 (12)C29—C28—C27121.27 (11)
C3—C2—H2A116.3 (9)C29—C28—H28A123.8 (9)
H3A—C3—C2124.2 (9)H29A—C29—C28118.7 (9)
C4—C3—C2118.58 (11)C30—C29—C28118.58 (11)
C4—C3—H3A116.9 (9)C30—C29—H29A122.7 (9)
H4A—C4—C3117.9 (9)H30A—C30—C29114.6 (9)
C5—C4—C3120.68 (11)C31—C30—C29120.78 (11)
C5—C4—H4A121.4 (9)C31—C30—H30A124.6 (9)
H5A—C5—C4117.3 (9)H31A—C31—C30119.7 (9)
C6—C5—C4121.56 (11)C32—C31—C30121.70 (11)
C6—C5—H5A121.0 (9)C32—C31—H31A118.6 (9)
C1—C6—N1119.13 (10)C27—C32—N3119.40 (10)
C5—C6—N1123.76 (11)C31—C32—N3123.94 (10)
C5—C6—C1117.10 (10)C31—C32—C27116.66 (10)
N1—C7—P1108.64 (8)N3—C33—P3111.60 (7)
H7A—C7—P1105.4 (9)H33A—C33—P3105.6 (9)
H7A—C7—N1118.3 (9)H33A—C33—N3111.9 (9)
H7B—C7—P1117.3 (8)H33B—C33—P3105.2 (8)
H7B—C7—N1108.7 (8)H33B—C33—N3113.7 (8)
H7B—C7—H7A98.8 (12)H33B—C33—H33A108.4 (12)
H8A—C8—P1103.6 (9)H34A—C34—P3104.2 (9)
C10—C8—P1117.22 (10)C36—C34—P3114.88 (9)
C10—C8—H8A103.6 (9)C36—C34—H34A110.1 (9)
C11—C8—P1110.53 (10)C37—C34—P3113.52 (9)
C11—C8—H8A110.1 (9)C37—C34—H34A102.7 (9)
C11—C8—C10111.12 (13)C37—C34—C36110.50 (10)
H9A—C9—P1104.9 (9)H35A—C35—P3106.4 (9)
C12—C9—P1110.00 (9)C38—C35—P3108.63 (8)
C12—C9—H9A107.1 (9)C38—C35—H35A109.2 (9)
C13—C9—P1116.87 (10)C39—C35—P3113.44 (9)
C13—C9—H9A108.8 (9)C39—C35—H35A107.4 (9)
C13—C9—C12108.78 (12)C39—C35—C38111.60 (11)
H10A—C10—C8113.0 (9)H36A—C36—C34112.1 (9)
H10B—C10—C8111.4 (9)H36B—C36—C34104.3 (9)
H10B—C10—H10A111.8 (13)H36B—C36—H36A112.6 (13)
H10C—C10—C8106.5 (9)H36C—C36—C34109.0 (9)
H10C—C10—H10A97.8 (12)H36C—C36—H36A114.1 (13)
H10C—C10—H10B115.6 (13)H36C—C36—H36B104.0 (13)
H11A—C11—C8101.4 (9)H37A—C37—C34106.6 (9)
H11B—C11—C8116.0 (9)H37B—C37—C34115.2 (9)
H11B—C11—H11A116.2 (13)H37B—C37—H37A121.7 (13)
H11C—C11—C8108.6 (9)H37C—C37—C34107.9 (9)
H11C—C11—H11A101.5 (13)H37C—C37—H37A113.4 (13)
H11C—C11—H11B111.7 (13)H37C—C37—H37B90.8 (13)
H12A—C12—C9105.6 (9)H38A—C38—C35109.4 (9)
H12B—C12—C9108.1 (9)H38B—C38—C35103.9 (9)
H12B—C12—H12A117.1 (13)H38B—C38—H38A119.1 (13)
H12C—C12—C9108.3 (9)H38C—C38—C35113.2 (9)
H12C—C12—H12A104.4 (13)H38C—C38—H38A104.7 (13)
H12C—C12—H12B112.9 (12)H38C—C38—H38B106.8 (13)
H13A—C13—C9120.8 (10)H39A—C39—C35118.7 (9)
H13B—C13—C9115.7 (9)H39B—C39—C35112.3 (9)
H13B—C13—H13A112.8 (13)H39B—C39—H39A100.2 (13)
H13C—C13—C9118.7 (10)H39C—C39—C35110.0 (9)
H13C—C13—H13A93.5 (13)H39C—C39—H39A106.0 (13)
H13C—C13—H13B89.1 (13)H39C—C39—H39B109.0 (13)
In1—N1—C6—C126.68 (9)N2—C19—C18—C17179.61 (12)
In1—N1—C6—C5152.11 (8)N3—C32—C27—N44.50 (13)
In1—N1—C7—P129.22 (6)N3—C32—C27—C28176.52 (11)
In1—N2—C19—C1426.87 (9)N3—C32—C31—C30178.45 (13)
In1—N2—C19—C18152.11 (8)N4—C1—C2—C3177.38 (11)
In1—N2—C20—P223.25 (7)N4—C1—C6—C5176.73 (10)
In1—N3—C32—C2721.98 (9)N4—C14—C15—C16178.39 (11)
In1—N3—C32—C31157.58 (8)N4—C14—C19—C18177.77 (10)
In1—N3—C33—P314.42 (7)N4—C27—C28—C29176.31 (12)
In1—N4—C1—C2157.18 (7)N4—C27—C32—C31175.91 (10)
In1—N4—C1—C619.47 (7)C1—C2—C3—C41.06 (14)
In1—N4—C14—C15157.00 (7)C1—C6—C5—C40.44 (13)
In1—N4—C14—C1920.86 (7)C2—C3—C4—C50.55 (15)
In1—N4—C27—C28156.87 (8)C3—C4—C5—C60.20 (15)
In1—N4—C27—C3224.15 (8)C14—C15—C16—C170.76 (14)
P1—C7—N1—C6169.70 (8)C14—C19—C18—C170.61 (13)
P2—C20—N2—C19169.15 (7)C15—C16—C17—C180.25 (15)
P3—C33—N3—C32160.21 (8)C16—C17—C18—C190.44 (16)
N1—C6—C1—N42.14 (12)C27—C28—C29—C300.13 (16)
N1—C6—C1—C2178.81 (11)C27—C32—C31—C301.12 (14)
N1—C6—C5—C4179.25 (12)C28—C29—C30—C311.84 (18)
N2—C19—C14—N41.30 (12)C29—C30—C31—C321.32 (18)
N2—C19—C14—C15179.17 (11)
(GOJNIF_HAR) top
Crystal data top
C39H62InN4NiP3Dx = 1.415 Mg m3
Mr = 853.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9537 reflections
a = 12.2127 (4) Åθ = 2.3–36.4°
b = 14.5402 (5) ŵ = 1.20 mm1
c = 22.5601 (8) ÅT = 100 K
V = 4006.1 (2) Å3Block, gold
Z = 40.14 × 0.08 × 0.06 mm
F(000) = 105.781
Data collection top
Bruker Photon-II CMOS
diffractometer
18741 reflections with I 2u(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
SADABS. R.Blessing, 1995
θmax = 36.4°, θmin = 2.3°
Tmin = 0.701, Tmax = 0.747h = 2020
237431 measured reflectionsk = 2424
19473 independent reflectionsl = 3737
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.023 w = 1/[σ2(Fo2) + (0.0161P)2 + 3.3112P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.051(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.35 e Å3
19473 reflectionsΔρmin = 0.62 e Å3
936 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
0 restraintsAbsolute structure parameter: 0.234 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.755807 (13)0.598646 (10)0.856159 (7)0.00891 (3)
H1A0.727 (3)0.574 (3)0.9266 (17)0.056 (11)*
H1B0.757 (4)0.635 (3)0.927 (2)0.080 (15)*
In10.798239 (6)0.580826 (5)0.749330 (4)0.008881 (15)
P10.91844 (3)0.52225 (2)0.864335 (14)0.00896 (5)
P20.59903 (3)0.52857 (2)0.829180 (14)0.00902 (5)
P30.75360 (3)0.75011 (2)0.835669 (14)0.00874 (5)
N10.96178 (8)0.53380 (7)0.74730 (6)0.01052 (15)
N20.67669 (9)0.48662 (8)0.72034 (5)0.01092 (18)
N30.78428 (9)0.71627 (7)0.71617 (5)0.01021 (17)
N40.83427 (9)0.56334 (7)0.64679 (5)0.00848 (16)
C10.95348 (10)0.57173 (8)0.64334 (5)0.00915 (17)
C21.00524 (11)0.59716 (9)0.59113 (6)0.0125 (2)
H2A0.957 (2)0.6113 (18)0.5529 (11)0.025 (6)*
C31.11901 (12)0.60861 (10)0.58837 (6)0.0143 (2)
H3A1.160 (2)0.629 (2)0.5486 (13)0.037 (7)*
C41.18033 (10)0.59552 (9)0.63977 (6)0.0138 (2)
H4A1.2671 (19)0.6043 (18)0.6379 (11)0.029 (6)
C51.12975 (10)0.57047 (9)0.69269 (6)0.0121 (2)
H5A1.178 (2)0.5614 (17)0.7321 (10)0.026 (6)
C61.01536 (11)0.55741 (9)0.69638 (6)0.0095 (2)
C71.01939 (11)0.53663 (10)0.80307 (6)0.0111 (2)
H7A1.0632 (19)0.6008 (17)0.8120 (11)0.025 (6)
H7B1.082 (2)0.4808 (19)0.8063 (11)0.031 (7)
C80.99541 (12)0.56224 (10)0.93122 (6)0.0138 (2)
H8A0.981 (2)0.6375 (18)0.9321 (12)0.032 (7)
C90.91079 (11)0.39464 (9)0.87150 (6)0.0135 (2)
H9A0.852 (2)0.3829 (18)0.9081 (12)0.029 (7)
C101.12044 (14)0.55059 (13)0.93045 (8)0.0220 (3)
H10A1.143 (3)0.479 (2)0.9271 (18)0.067 (11)
H10B1.160 (2)0.587 (3)0.8936 (13)0.053 (9)
H10C1.155 (2)0.580 (3)0.9722 (13)0.049 (9)
C110.94556 (17)0.52153 (15)0.98765 (7)0.0263 (3)
H11A0.979 (4)0.554 (3)1.0251 (13)0.084 (15)
H11B0.862 (3)0.535 (2)0.9907 (14)0.046 (8)*
H11C0.953 (3)0.447 (2)0.9914 (14)0.062 (12)
C120.86448 (14)0.35267 (10)0.81439 (7)0.0182 (3)
H12A0.849 (3)0.2809 (17)0.8216 (13)0.048 (9)
H12B0.786 (2)0.3855 (19)0.8018 (13)0.040 (8)
H12C0.924 (3)0.362 (2)0.7787 (11)0.048 (10)
C131.01692 (15)0.34496 (11)0.88746 (9)0.0234 (3)
H13A1.005 (3)0.272 (2)0.8865 (14)0.049 (9)*
H13B1.083 (2)0.3606 (19)0.8545 (15)0.042 (8)
H13C1.048 (3)0.362 (2)0.9308 (15)0.053 (10)
C140.78966 (10)0.47284 (8)0.63325 (5)0.00964 (18)
C150.82602 (11)0.42267 (10)0.58484 (5)0.01201 (19)
H15A0.8904 (19)0.4519 (16)0.5573 (10)0.019 (5)*
C160.78525 (12)0.33496 (9)0.57247 (6)0.0147 (2)
H16A0.815 (2)0.2968 (17)0.5338 (11)0.030 (7)
C170.70729 (13)0.29739 (9)0.61049 (6)0.0156 (2)
H17A0.676 (3)0.2291 (18)0.6023 (12)0.040 (8)
C180.67002 (12)0.34631 (9)0.65962 (6)0.0138 (2)
H18A0.612 (2)0.3151 (19)0.6913 (11)0.027 (6)
C190.70909 (10)0.43552 (8)0.67264 (5)0.01006 (18)
C200.60328 (11)0.44849 (9)0.76426 (6)0.0115 (2)
H20A0.628 (2)0.3794 (18)0.7806 (13)0.033 (7)
H20B0.5193 (18)0.4393 (16)0.7461 (13)0.027 (6)
C210.53629 (11)0.45621 (9)0.88800 (6)0.0128 (2)
H21A0.465 (2)0.422 (2)0.8679 (11)0.027 (6)*
C220.48065 (10)0.60402 (10)0.80768 (6)0.0121 (2)
H22A0.478 (2)0.6577 (17)0.8413 (11)0.031 (7)
C230.61405 (14)0.38130 (12)0.91017 (7)0.0202 (3)
H23A0.573 (2)0.337 (2)0.9433 (13)0.036 (7)*
H23B0.640 (3)0.3364 (19)0.8756 (13)0.042 (8)
H23C0.684 (2)0.414 (2)0.9314 (12)0.041 (8)
C240.49919 (14)0.51662 (12)0.94002 (6)0.0183 (3)
H24A0.443 (2)0.574 (2)0.9267 (11)0.038 (8)
H24B0.463 (3)0.4754 (19)0.9726 (11)0.038 (8)
H24C0.569 (2)0.551 (2)0.9607 (13)0.040 (8)
C250.49935 (11)0.64750 (10)0.74678 (8)0.0168 (2)
H25A0.436 (2)0.6986 (18)0.7376 (11)0.033 (7)
H25B0.578 (2)0.6809 (19)0.7409 (10)0.029 (6)
H25C0.494 (2)0.595 (2)0.7130 (12)0.039 (7)*
C260.36765 (12)0.55815 (11)0.80854 (7)0.0171 (2)
H26A0.306 (2)0.6093 (18)0.7969 (14)0.037 (7)
H26B0.364 (2)0.5028 (19)0.7777 (12)0.037 (7)
H26C0.344 (2)0.534 (2)0.8512 (12)0.043 (8)
C270.77587 (10)0.64131 (8)0.62076 (5)0.00994 (19)
C280.74260 (13)0.64002 (9)0.56205 (6)0.0140 (2)
H28A0.7542 (19)0.5773 (16)0.5369 (10)0.021 (5)
C290.69212 (14)0.71649 (10)0.53620 (6)0.0177 (2)
H29A0.669 (3)0.7150 (19)0.4909 (12)0.043 (9)
C300.67545 (13)0.79434 (10)0.57069 (6)0.0165 (2)
H30A0.638 (3)0.8550 (18)0.5518 (13)0.036 (8)
C310.70546 (12)0.79591 (9)0.63023 (6)0.0128 (2)
H31A0.693 (3)0.8574 (17)0.6538 (13)0.041 (8)
C320.75543 (11)0.71946 (8)0.65751 (5)0.00952 (18)
C330.74804 (11)0.78800 (8)0.75567 (6)0.01132 (18)
H33A0.6630 (17)0.8081 (17)0.7469 (13)0.029 (6)
H33B0.797 (2)0.8504 (15)0.7520 (11)0.029 (6)
C340.62754 (11)0.80867 (9)0.86343 (6)0.0115 (2)
H34A0.5636 (19)0.7829 (17)0.8332 (10)0.021 (6)
C350.86861 (11)0.82275 (9)0.86203 (6)0.0126 (2)
H35A0.849 (2)0.8921 (16)0.8463 (12)0.032 (7)
C360.63050 (12)0.91388 (10)0.85998 (6)0.0158 (2)
H36A0.657 (2)0.937 (2)0.8174 (12)0.040 (8)
H36B0.550 (2)0.9423 (19)0.8692 (13)0.038 (8)
H36C0.685 (3)0.9425 (19)0.8938 (13)0.043 (8)
C370.59270 (14)0.77704 (11)0.92534 (7)0.0174 (2)
H37A0.514 (2)0.805 (2)0.9364 (15)0.054 (10)
H37B0.586 (3)0.7045 (17)0.9288 (13)0.045 (9)
H37C0.648 (2)0.8012 (19)0.9578 (11)0.029 (6)
C380.97439 (12)0.78990 (11)0.83199 (7)0.0166 (2)
H38A1.036 (3)0.840 (2)0.8348 (16)0.052 (10)
H38B1.001 (2)0.7265 (18)0.8516 (12)0.036 (7)
H38C0.961 (2)0.778 (2)0.7844 (11)0.032 (7)
C390.87995 (13)0.82433 (11)0.92965 (7)0.0175 (2)
H39A0.955 (3)0.858 (3)0.9429 (16)0.063 (12)
H39B0.817 (2)0.862 (2)0.9510 (12)0.042 (8)
H39C0.877 (2)0.755 (2)0.9479 (13)0.038 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.00806 (6)0.00781 (6)0.01086 (6)0.00034 (5)0.00038 (5)0.00003 (5)
In10.00908 (3)0.00840 (3)0.00917 (3)0.00011 (2)0.00015 (3)0.00014 (3)
P10.00966 (12)0.00914 (12)0.00807 (12)0.00075 (10)0.00067 (9)0.00064 (10)
P20.00826 (12)0.01045 (12)0.00835 (12)0.00177 (10)0.00046 (9)0.00026 (10)
P30.01059 (12)0.00735 (11)0.00828 (11)0.00014 (11)0.00058 (10)0.00085 (9)
N10.0089 (3)0.0133 (4)0.0093 (4)0.0010 (3)0.0001 (4)0.0013 (4)
N20.0114 (4)0.0112 (4)0.0101 (4)0.0022 (3)0.0012 (3)0.0025 (3)
N30.0138 (5)0.0087 (4)0.0081 (4)0.0016 (3)0.0008 (3)0.0002 (3)
N40.0100 (4)0.0085 (4)0.0070 (4)0.0009 (3)0.0008 (3)0.0001 (3)
C10.0098 (4)0.0097 (4)0.0079 (4)0.0005 (4)0.0014 (3)0.0000 (4)
C20.0140 (5)0.0132 (5)0.0103 (5)0.0000 (4)0.0026 (4)0.0007 (4)
C30.0144 (5)0.0157 (5)0.0129 (5)0.0011 (4)0.0043 (4)0.0012 (4)
C40.0108 (5)0.0148 (5)0.0156 (5)0.0008 (4)0.0036 (4)0.0006 (4)
H4A0.017 (12)0.042 (16)0.028 (14)0.002 (12)0.005 (11)0.003 (13)
C50.0097 (5)0.0145 (5)0.0121 (5)0.0002 (4)0.0007 (4)0.0005 (4)
H5A0.025 (14)0.026 (14)0.026 (14)0.007 (11)0.010 (11)0.013 (11)
C60.0091 (5)0.0106 (5)0.0088 (5)0.0006 (4)0.0011 (4)0.0000 (4)
C70.0096 (5)0.0140 (5)0.0098 (5)0.0011 (4)0.0003 (4)0.0007 (4)
H7A0.016 (13)0.027 (15)0.032 (15)0.007 (12)0.011 (11)0.004 (12)
H7B0.031 (16)0.040 (17)0.023 (14)0.016 (14)0.014 (12)0.002 (13)
C80.0152 (5)0.0162 (6)0.0102 (5)0.0013 (4)0.0021 (4)0.0004 (4)
H8A0.047 (19)0.022 (14)0.026 (16)0.013 (14)0.009 (14)0.007 (12)
C90.0145 (5)0.0103 (5)0.0156 (5)0.0015 (4)0.0005 (4)0.0027 (4)
H9A0.030 (16)0.025 (15)0.033 (16)0.002 (12)0.011 (13)0.017 (12)
C100.0162 (6)0.0287 (8)0.0212 (7)0.0007 (6)0.0078 (5)0.0036 (6)
H10A0.05 (2)0.04 (2)0.11 (3)0.009 (19)0.03 (2)0.02 (2)
H10B0.036 (19)0.08 (3)0.041 (19)0.01 (2)0.002 (15)0.02 (2)
H10C0.039 (18)0.08 (3)0.032 (17)0.016 (19)0.009 (14)0.010 (18)
C110.0334 (9)0.0344 (9)0.0111 (6)0.0102 (7)0.0003 (6)0.0007 (6)
H11A0.17 (5)0.07 (3)0.012 (16)0.02 (3)0.02 (2)0.010 (16)
H11C0.12 (3)0.025 (17)0.04 (2)0.04 (2)0.02 (2)0.003 (14)
C120.0241 (7)0.0110 (5)0.0194 (6)0.0006 (5)0.0019 (5)0.0018 (5)
H12A0.08 (3)0.007 (12)0.05 (2)0.006 (15)0.031 (19)0.001 (13)
H12B0.037 (18)0.034 (17)0.048 (19)0.003 (14)0.012 (15)0.013 (14)
H12C0.09 (3)0.05 (2)0.003 (12)0.02 (2)0.007 (15)0.001 (13)
C130.0200 (7)0.0139 (6)0.0363 (9)0.0054 (5)0.0056 (6)0.0051 (6)
H13B0.024 (16)0.028 (16)0.07 (2)0.016 (13)0.019 (17)0.002 (17)
H13C0.06 (2)0.05 (2)0.05 (2)0.005 (19)0.029 (19)0.026 (18)
C140.0117 (4)0.0088 (4)0.0084 (4)0.0012 (4)0.0000 (4)0.0014 (3)
C150.0149 (5)0.0115 (5)0.0097 (4)0.0001 (4)0.0011 (4)0.0020 (4)
C160.0182 (6)0.0127 (5)0.0133 (5)0.0007 (4)0.0010 (4)0.0057 (4)
H16A0.035 (16)0.023 (14)0.031 (15)0.005 (13)0.009 (13)0.022 (12)
C170.0180 (6)0.0120 (5)0.0168 (5)0.0029 (5)0.0007 (5)0.0055 (4)
H17A0.06 (2)0.028 (15)0.029 (16)0.012 (15)0.021 (15)0.016 (13)
C180.0142 (5)0.0119 (5)0.0154 (5)0.0030 (4)0.0014 (4)0.0039 (4)
H18A0.017 (13)0.040 (17)0.024 (14)0.019 (12)0.011 (11)0.001 (12)
C190.0104 (4)0.0099 (4)0.0099 (4)0.0007 (4)0.0002 (4)0.0023 (3)
C200.0106 (5)0.0120 (4)0.0118 (5)0.0027 (4)0.0014 (4)0.0020 (3)
H20A0.021 (15)0.018 (14)0.06 (2)0.005 (12)0.002 (13)0.005 (13)
H20B0.019 (12)0.032 (14)0.030 (14)0.008 (10)0.001 (14)0.013 (14)
C210.0125 (5)0.0153 (5)0.0106 (5)0.0039 (4)0.0007 (4)0.0010 (4)
C220.0093 (4)0.0152 (5)0.0117 (5)0.0003 (4)0.0005 (4)0.0020 (4)
H22A0.046 (18)0.025 (15)0.022 (14)0.008 (13)0.000 (13)0.016 (11)
C230.0205 (7)0.0218 (7)0.0184 (6)0.0002 (5)0.0023 (5)0.0075 (5)
H23B0.05 (2)0.030 (17)0.044 (19)0.020 (15)0.001 (16)0.022 (14)
H23C0.036 (17)0.051 (19)0.035 (16)0.000 (16)0.023 (14)0.000 (15)
C240.0236 (7)0.0213 (6)0.0100 (5)0.0057 (5)0.0029 (5)0.0011 (5)
H24A0.042 (18)0.05 (2)0.017 (14)0.002 (17)0.010 (13)0.004 (15)
H24B0.07 (2)0.027 (16)0.015 (13)0.021 (15)0.015 (14)0.009 (12)
H24C0.026 (16)0.05 (2)0.041 (18)0.017 (14)0.012 (14)0.000 (15)
C250.0166 (5)0.0185 (5)0.0151 (5)0.0028 (4)0.0011 (5)0.0024 (6)
H25A0.034 (15)0.044 (17)0.021 (16)0.019 (13)0.001 (12)0.015 (13)
H25B0.030 (14)0.050 (17)0.007 (13)0.012 (12)0.003 (11)0.000 (12)
C260.0101 (5)0.0228 (6)0.0184 (6)0.0013 (5)0.0011 (4)0.0034 (5)
H26A0.008 (12)0.028 (15)0.07 (2)0.000 (12)0.017 (14)0.006 (15)
H26B0.031 (16)0.039 (17)0.041 (17)0.015 (14)0.005 (13)0.022 (14)
H26C0.023 (15)0.07 (2)0.035 (17)0.005 (15)0.013 (13)0.007 (16)
C270.0131 (5)0.0091 (4)0.0076 (4)0.0015 (3)0.0007 (3)0.0000 (3)
C280.0200 (6)0.0125 (5)0.0094 (5)0.0041 (5)0.0029 (4)0.0014 (4)
H28A0.016 (11)0.018 (11)0.030 (13)0.007 (11)0.008 (11)0.008 (11)
C290.0261 (7)0.0169 (5)0.0102 (5)0.0083 (5)0.0056 (5)0.0006 (4)
H29A0.06 (2)0.040 (18)0.028 (15)0.017 (16)0.028 (15)0.021 (13)
C300.0237 (6)0.0147 (5)0.0110 (5)0.0082 (5)0.0030 (4)0.0012 (4)
H30A0.05 (2)0.020 (15)0.040 (18)0.014 (14)0.002 (15)0.002 (13)
C310.0171 (5)0.0111 (4)0.0102 (5)0.0046 (4)0.0011 (4)0.0007 (4)
H31A0.048 (19)0.022 (14)0.053 (19)0.021 (14)0.007 (16)0.021 (13)
C320.0117 (5)0.0084 (4)0.0084 (4)0.0018 (4)0.0008 (4)0.0002 (3)
C330.0157 (5)0.0084 (4)0.0099 (5)0.0013 (4)0.0002 (4)0.0005 (4)
H33A0.013 (11)0.039 (15)0.036 (15)0.018 (10)0.012 (14)0.013 (16)
H33B0.044 (15)0.029 (13)0.015 (12)0.020 (12)0.008 (15)0.012 (12)
C340.0134 (5)0.0107 (5)0.0104 (5)0.0011 (4)0.0005 (4)0.0010 (4)
H34A0.015 (12)0.031 (15)0.016 (12)0.009 (11)0.002 (10)0.004 (11)
C350.0140 (5)0.0104 (5)0.0133 (5)0.0022 (4)0.0006 (4)0.0016 (4)
H35A0.050 (19)0.012 (13)0.034 (16)0.005 (12)0.009 (14)0.006 (12)
C360.0202 (6)0.0112 (5)0.0160 (5)0.0033 (4)0.0009 (4)0.0008 (5)
H36A0.039 (17)0.045 (19)0.037 (17)0.012 (15)0.016 (14)0.013 (14)
H36B0.029 (16)0.034 (18)0.05 (2)0.005 (13)0.019 (15)0.020 (15)
H36C0.06 (2)0.028 (16)0.045 (19)0.007 (15)0.019 (16)0.001 (14)
C370.0220 (6)0.0173 (6)0.0129 (5)0.0012 (5)0.0037 (5)0.0005 (4)
H37A0.032 (18)0.07 (3)0.06 (2)0.009 (18)0.037 (16)0.002 (19)
H37B0.08 (2)0.007 (12)0.047 (19)0.005 (15)0.024 (18)0.000 (12)
H37C0.035 (16)0.034 (16)0.020 (14)0.004 (13)0.001 (12)0.002 (12)
C380.0142 (5)0.0178 (6)0.0177 (6)0.0041 (5)0.0013 (5)0.0028 (5)
H38A0.034 (18)0.034 (18)0.09 (3)0.017 (15)0.018 (18)0.006 (17)
H38B0.053 (19)0.019 (14)0.035 (17)0.002 (13)0.001 (15)0.003 (13)
H38C0.029 (16)0.05 (2)0.012 (13)0.006 (14)0.001 (12)0.008 (13)
C390.0188 (6)0.0199 (6)0.0137 (6)0.0030 (5)0.0027 (5)0.0039 (5)
H39A0.05 (2)0.09 (3)0.06 (2)0.03 (2)0.018 (19)0.00 (2)
H39B0.036 (18)0.05 (2)0.036 (17)0.018 (15)0.014 (14)0.020 (15)
Geometric parameters (Å, º) top
Ni1—H1A1.67 (4)C14—C191.4327 (17)
Ni1—H1B1.68 (5)C15—H15A1.09 (2)
Ni1—In12.4787 (2)C15—C161.3973 (19)
Ni1—P12.2832 (4)C16—H16A1.09 (2)
Ni1—P22.2527 (4)C16—C171.393 (2)
Ni1—P32.2505 (4)C17—H17A1.08 (3)
H1A—H1B0.96 (6)C17—C181.3934 (19)
In1—N12.1116 (10)C18—H18A1.11 (2)
In1—N22.1231 (11)C18—C191.4128 (18)
In1—N32.1136 (11)C20—H20A1.11 (3)
In1—N42.3684 (11)C20—H20B1.11 (2)
P1—C71.8639 (14)C21—H21A1.10 (3)
P1—C81.8704 (14)C21—C231.529 (2)
P1—C91.8648 (14)C21—C241.534 (2)
P2—C201.8717 (13)C22—H22A1.09 (2)
P2—C211.8587 (13)C22—C251.529 (2)
P2—C221.8786 (14)C22—C261.5328 (19)
P3—C331.8882 (13)C23—H23A1.11 (3)
P3—C341.8675 (13)C23—H23B1.06 (3)
P3—C351.8553 (13)C23—H23C1.09 (3)
N1—C61.3659 (18)C24—H24A1.12 (3)
N1—C71.4422 (18)C24—H24B1.05 (2)
N2—C191.3663 (16)C24—H24C1.09 (3)
N2—C201.4466 (17)C25—H25A1.10 (2)
N3—C321.3702 (16)C25—H25B1.08 (2)
N3—C331.4415 (16)C25—H25C1.08 (3)
N4—C11.4631 (16)C26—H26A1.09 (2)
N4—C141.4566 (16)C26—H26B1.06 (2)
N4—C271.4625 (16)C26—H26C1.06 (3)
C1—C21.3870 (17)C27—C281.3854 (17)
C1—C61.4304 (18)C27—C321.4287 (17)
C2—H2A1.07 (2)C28—H28A1.08 (2)
C2—C31.4008 (19)C28—C291.3988 (19)
C3—H3A1.07 (3)C29—H29A1.06 (3)
C3—C41.394 (2)C29—C301.389 (2)
C4—H4A1.07 (2)C30—H30A1.08 (3)
C4—C51.3926 (19)C30—C311.3925 (19)
C5—H5A1.08 (2)C31—H31A1.05 (2)
C5—C61.4123 (19)C31—C321.4095 (17)
C7—H7A1.09 (2)C33—H33A1.10 (2)
C7—H7B1.11 (3)C33—H33B1.09 (2)
C8—H8A1.11 (3)C34—H34A1.10 (2)
C8—C101.536 (2)C34—C361.5322 (19)
C8—C111.530 (2)C34—C371.531 (2)
C9—H9A1.11 (3)C35—H35A1.09 (2)
C9—C121.534 (2)C35—C381.535 (2)
C9—C131.527 (2)C35—C391.532 (2)
C10—H10A1.08 (3)C36—H36A1.07 (3)
C10—H10B1.10 (3)C36—H36B1.09 (3)
C10—H10C1.12 (3)C36—H36C1.10 (3)
C11—H11A1.05 (3)C37—H37A1.07 (3)
C11—H11B1.04 (3)C37—H37B1.06 (2)
C11—H11C1.09 (3)C37—H37C1.06 (3)
C12—H12A1.07 (3)C38—H38A1.05 (3)
C12—H12B1.11 (3)C38—H38B1.07 (3)
C12—H12C1.09 (3)C38—H38C1.10 (2)
C13—H13A1.07 (3)C39—H39A1.08 (3)
C13—H13B1.12 (3)C39—H39B1.06 (2)
C13—H13C1.08 (3)C39—H39C1.09 (3)
C14—C151.3864 (17)
H1B—Ni1—H1A33.3 (19)C15—C14—N4121.38 (11)
In1—Ni1—H1A161.8 (14)C19—C14—N4117.97 (10)
In1—Ni1—H1B162.4 (17)C19—C14—C15120.62 (11)
P1—Ni1—H1A90.2 (13)H15A—C15—C14118.4 (12)
P1—Ni1—H1B94.1 (17)C16—C15—C14121.57 (12)
P1—Ni1—In181.131 (10)C16—C15—H15A120.0 (12)
P2—Ni1—H1A89.0 (14)H16A—C16—C15120.3 (14)
P2—Ni1—H1B114.0 (18)C17—C16—C15118.58 (12)
P2—Ni1—In182.397 (10)C17—C16—H16A121.1 (14)
P2—Ni1—P1122.760 (14)H17A—C17—C16119.6 (14)
P3—Ni1—H1A113.6 (14)C18—C17—C16120.85 (12)
P3—Ni1—H1B83.3 (16)C18—C17—H17A119.5 (14)
P3—Ni1—In184.553 (10)H18A—C18—C17121.0 (14)
P3—Ni1—P1120.206 (14)C19—C18—C17121.59 (13)
P3—Ni1—P2112.148 (14)C19—C18—H18A117.4 (14)
H1B—H1A—Ni174 (4)C14—C19—N2118.78 (11)
H1A—H1B—Ni172 (4)C18—C19—N2124.42 (12)
N1—In1—Ni1104.64 (4)C18—C19—C14116.79 (11)
N2—In1—Ni1102.76 (3)N2—C20—P2108.35 (9)
N2—In1—N1116.47 (4)H20A—C20—P2108.1 (15)
N3—In1—Ni1103.29 (3)H20A—C20—N2114.1 (14)
N3—In1—N1111.74 (4)H20B—C20—P2109.7 (13)
N3—In1—N2115.83 (4)H20B—C20—N2111.4 (15)
N4—In1—Ni1178.63 (3)H20B—C20—H20A105.0 (19)
N4—In1—N176.60 (4)H21A—C21—P2106.8 (14)
N4—In1—N276.10 (4)C23—C21—P2112.38 (10)
N4—In1—N376.66 (4)C23—C21—H21A107.4 (15)
C7—P1—Ni1117.45 (5)C24—C21—P2110.11 (10)
C8—P1—Ni1110.55 (5)C24—C21—H21A110.2 (13)
C8—P1—C7103.35 (6)C24—C21—C23109.94 (12)
C9—P1—Ni1116.58 (5)H22A—C22—P2105.3 (15)
C9—P1—C7102.07 (6)C25—C22—P2111.00 (9)
C9—P1—C8105.34 (6)C25—C22—H22A109.5 (14)
C20—P2—Ni1117.98 (4)C26—C22—P2115.82 (10)
C21—P2—Ni1114.42 (4)C26—C22—H22A105.9 (15)
C21—P2—C20102.59 (6)C26—C22—C25109.01 (12)
C22—P2—Ni1117.37 (4)H23A—C23—C21110.4 (16)
C22—P2—C20100.52 (6)H23B—C23—C21112.3 (14)
C22—P2—C21101.40 (6)H23B—C23—H23A106 (2)
C33—P3—Ni1118.84 (4)H23C—C23—C21108.4 (16)
C34—P3—Ni1112.78 (4)H23C—C23—H23A108 (2)
C34—P3—C3399.08 (6)H23C—C23—H23B111 (2)
C35—P3—Ni1118.83 (5)H24A—C24—C21113.7 (14)
C35—P3—C3399.64 (6)H24B—C24—C21109.5 (15)
C35—P3—C34104.90 (6)H24B—C24—H24A111 (2)
C6—N1—In1112.96 (9)H24C—C24—C21111.0 (16)
C7—N1—In1115.67 (9)H24C—C24—H24A105 (2)
C7—N1—C6119.52 (10)H24C—C24—H24B107 (2)
C19—N2—In1113.02 (8)H25A—C25—C22110.1 (13)
C20—N2—In1118.00 (8)H25B—C25—C22115.3 (13)
C20—N2—C19120.70 (11)H25B—C25—H25A107 (2)
C32—N3—In1113.21 (8)H25C—C25—C22109.2 (15)
C33—N3—In1118.69 (8)H25C—C25—H25A108 (2)
C33—N3—C32119.57 (10)H25C—C25—H25B107 (2)
C1—N4—In1103.17 (7)H26A—C26—C22108.7 (13)
C14—N4—In1103.43 (7)H26B—C26—C22111.0 (15)
C14—N4—C1115.87 (10)H26B—C26—H26A109 (2)
C27—N4—In1102.62 (7)H26C—C26—C22113.7 (15)
C27—N4—C1113.53 (10)H26C—C26—H26A105 (2)
C27—N4—C14115.70 (10)H26C—C26—H26B109 (2)
C2—C1—N4121.39 (11)C28—C27—N4121.09 (11)
C6—C1—N4117.98 (11)C32—C27—N4117.95 (10)
C6—C1—C2120.56 (11)C32—C27—C28120.96 (11)
H2A—C2—C1119.0 (14)H28A—C28—C27118.3 (13)
C3—C2—C1121.43 (12)C29—C28—C27121.14 (12)
C3—C2—H2A119.5 (14)C29—C28—H28A120.6 (13)
H3A—C3—C2122.6 (16)H29A—C29—C28120.3 (15)
C4—C3—C2118.67 (12)C30—C29—C28118.61 (12)
C4—C3—H3A118.7 (16)C30—C29—H29A121.1 (15)
H4A—C4—C3119.0 (13)H30A—C30—C29120.4 (15)
C5—C4—C3120.72 (12)C31—C30—C29121.02 (13)
C5—C4—H4A120.3 (13)C31—C30—H30A118.6 (15)
H5A—C5—C4119.6 (14)H31A—C31—C30117.5 (16)
C6—C5—C4121.62 (12)C32—C31—C30121.49 (12)
C6—C5—H5A118.7 (14)C32—C31—H31A120.9 (16)
C1—C6—N1119.14 (12)C27—C32—N3119.25 (11)
C5—C6—N1123.86 (12)C31—C32—N3124.05 (11)
C5—C6—C1116.99 (12)C31—C32—C27116.70 (11)
N1—C7—P1108.73 (9)N3—C33—P3111.64 (8)
H7A—C7—P1106.4 (13)H33A—C33—P3106.5 (16)
H7A—C7—N1115.0 (12)H33A—C33—N3111.8 (14)
H7B—C7—P1108.7 (14)H33B—C33—P3107.2 (14)
H7B—C7—N1111.6 (13)H33B—C33—N3112.7 (13)
H7B—C7—H7A106.1 (19)H33B—C33—H33A106.6 (19)
H8A—C8—P1104.1 (14)H34A—C34—P3102.9 (12)
C10—C8—P1117.13 (11)C36—C34—P3114.75 (10)
C10—C8—H8A105.3 (16)C36—C34—H34A108.9 (13)
C11—C8—P1110.54 (11)C37—C34—P3113.46 (10)
C11—C8—H8A107.8 (15)C37—C34—H34A105.3 (12)
C11—C8—C10111.23 (14)C37—C34—C36110.67 (11)
H9A—C9—P1104.5 (13)H35A—C35—P3104.8 (15)
C12—C9—P1109.97 (9)C38—C35—P3108.57 (9)
C12—C9—H9A108.9 (13)C38—C35—H35A109.0 (15)
C13—C9—P1116.65 (11)C39—C35—P3113.34 (10)
C13—C9—H9A107.7 (15)C39—C35—H35A109.2 (14)
C13—C9—C12108.84 (13)C39—C35—C38111.61 (12)
H10A—C10—C8111.3 (19)H36A—C36—C34111.6 (16)
H10B—C10—C8113.1 (17)H36B—C36—C34110.4 (15)
H10B—C10—H10A108 (3)H36B—C36—H36A109 (2)
H10C—C10—C8109.1 (16)H36C—C36—C34111.0 (15)
H10C—C10—H10A109 (3)H36C—C36—H36A108 (2)
H10C—C10—H10B106 (2)H36C—C36—H36B106 (2)
H11A—C11—C8110 (2)H37A—C37—C34110.3 (18)
H11B—C11—C8111.7 (17)H37B—C37—C34112.8 (15)
H11B—C11—H11A104 (3)H37B—C37—H37A107 (3)
H11C—C11—C8114.6 (19)H37C—C37—C34110.7 (14)
H11C—C11—H11A110 (3)H37C—C37—H37A107 (2)
H11C—C11—H11B106 (3)H37C—C37—H37B109 (2)
H12A—C12—C9108.9 (15)H38A—C38—C35110.7 (19)
H12B—C12—C9111.3 (14)H38B—C38—C35110.1 (15)
H12B—C12—H12A108 (2)H38B—C38—H38A111 (2)
H12C—C12—C9108.7 (16)H38C—C38—C35110.9 (14)
H12C—C12—H12A111 (2)H38C—C38—H38A106 (2)
H12C—C12—H12B109 (2)H38C—C38—H38B108 (2)
H13A—C13—C9110.4 (17)H39A—C39—C35111.1 (19)
H13B—C13—C9111.1 (15)H39B—C39—C35113.2 (16)
H13B—C13—H13A107 (2)H39B—C39—H39A105 (3)
H13C—C13—C9113.9 (19)H39C—C39—C35111.0 (15)
H13C—C13—H13A107 (2)H39C—C39—H39A110 (3)
H13C—C13—H13B107 (3)H39C—C39—H39B107 (2)
In1—N1—C6—C126.68 (9)N2—C19—C18—C17179.33 (14)
In1—N1—C6—C5152.14 (9)N3—C32—C27—N44.31 (14)
In1—N1—C7—P129.28 (6)N3—C32—C27—C28176.51 (12)
In1—N2—C19—C1426.52 (10)N3—C32—C31—C30178.37 (14)
In1—N2—C19—C18152.16 (9)N4—C1—C2—C3177.54 (12)
In1—N2—C20—P223.11 (8)N4—C1—C6—C5176.85 (11)
In1—N3—C32—C2722.21 (10)N4—C14—C15—C16178.52 (12)
In1—N3—C32—C31157.51 (9)N4—C14—C19—C18177.85 (11)
In1—N3—C33—P314.30 (8)N4—C27—C28—C29176.44 (13)
In1—N4—C1—C2157.31 (8)N4—C27—C32—C31175.96 (12)
In1—N4—C1—C619.60 (8)C1—C2—C3—C41.13 (15)
In1—N4—C14—C15157.01 (8)C1—C6—C5—C40.45 (14)
In1—N4—C14—C1921.05 (8)C2—C3—C4—C50.76 (16)
In1—N4—C27—C28156.75 (9)C3—C4—C5—C60.03 (16)
In1—N4—C27—C3224.07 (8)C14—C15—C16—C170.86 (16)
P1—C7—N1—C6169.60 (8)C14—C19—C18—C170.62 (14)
P2—C20—N2—C19169.29 (8)C15—C16—C17—C180.46 (16)
P3—C33—N3—C32160.12 (9)C16—C17—C18—C190.29 (18)
N1—C6—C1—N42.06 (13)C27—C28—C29—C300.19 (18)
N1—C6—C1—C2178.99 (12)C27—C32—C31—C301.35 (15)
N1—C6—C5—C4179.30 (13)C28—C29—C30—C311.70 (19)
N2—C19—C14—N40.93 (13)C29—C30—C31—C321.09 (19)
N2—C19—C14—C15179.01 (12)
(GOJNIF_HAR_NoMoRe_1) top
Crystal data top
C39H62InN4NiP3Dx = 1.415 Mg m3
Mr = 853.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9537 reflections
a = 12.2127 (4) Åθ = 2.3–36.4°
b = 14.5402 (5) ŵ = 1.20 mm1
c = 22.5601 (8) ÅT = 100 K
V = 4006.1 (2) Å3Block, gold
Z = 40.14 × 0.08 × 0.06 mm
F(000) = 1784.150
Data collection top
Bruker Photon-II CMOS
diffractometer
18741 reflections with I 2u(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
SADABS. R.Blessing, 1995
θmax = 36.4°, θmin = 2.3°
Tmin = 0.701, Tmax = 0.747h = 2020
237431 measured reflectionsk = 2424
19473 independent reflectionsl = 3737
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullOnly H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.016 w = 1/[σ2(Fo2) + (0.0103P)2 + 0.7427P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.031(Δ/σ)max = 0.0002
S = 1.05Δρmax = 0.35 e Å3
19473 reflectionsΔρmin = 0.50 e Å3
619 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
0 restraintsAbsolute structure parameter: 0.004 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.755816 (8)0.598648 (6)0.856146 (5)0.009166 (17)
H1A0.7290 (15)0.5718 (13)0.9262 (7)0.036333
H1B0.7578 (17)0.6349 (12)0.9268 (7)0.035000
In10.798238 (4)0.580829 (3)0.749320 (3)0.008179 (9)
P10.918447 (17)0.522247 (14)0.864340 (9)0.00922 (3)
P20.599033 (17)0.528563 (14)0.829176 (9)0.00932 (3)
P30.753610 (18)0.750099 (14)0.835675 (9)0.00903 (3)
N10.96176 (5)0.53380 (4)0.74725 (4)0.01081 (10)
N20.67664 (6)0.48665 (5)0.72035 (3)0.01129 (12)
N30.78426 (6)0.71631 (4)0.71617 (3)0.01057 (11)
N40.83423 (5)0.56340 (4)0.64679 (3)0.00877 (10)
C10.95347 (6)0.57173 (5)0.64335 (3)0.00949 (11)
C21.00529 (7)0.59714 (6)0.59112 (4)0.01272 (13)
H2A0.9563 (12)0.6122 (10)0.5535 (6)0.028000
C31.11899 (7)0.60859 (6)0.58834 (4)0.01462 (14)
H3A1.1602 (12)0.6282 (11)0.5483 (6)0.032000
C41.18035 (6)0.59548 (6)0.63979 (4)0.01414 (14)
H4A1.2687 (11)0.6061 (10)0.6382 (6)0.030333
C51.12980 (6)0.57045 (6)0.69272 (4)0.01235 (13)
H5A1.1800 (11)0.5618 (10)0.7326 (6)0.027667
C61.01533 (7)0.55740 (6)0.69641 (4)0.00980 (13)
C71.01950 (7)0.53659 (6)0.80306 (4)0.01149 (14)
H7A1.0637 (12)0.6015 (10)0.8121 (6)0.028000
H7B1.0815 (12)0.4811 (10)0.8056 (6)0.029000
C80.99545 (7)0.56226 (6)0.93121 (4)0.01421 (14)
H8A0.9795 (12)0.6371 (10)0.9324 (6)0.027667
C90.91074 (7)0.39464 (6)0.87150 (4)0.01382 (14)
H9A0.8498 (12)0.3827 (10)0.9076 (6)0.029000
C101.12036 (8)0.55054 (8)0.93050 (5)0.02230 (19)
H10A1.1449 (14)0.4788 (12)0.9259 (8)0.049667
H10B1.1554 (13)0.5777 (15)0.9727 (7)0.051667
H10C1.1594 (13)0.5875 (13)0.8930 (7)0.041333
C110.94543 (10)0.52162 (9)0.98766 (4)0.0271 (2)
H11A0.9812 (15)0.5542 (12)1.0261 (7)0.042000
H11B0.9552 (13)0.4465 (13)0.9908 (7)0.046333
H11C0.8629 (15)0.5370 (10)0.9912 (7)0.040000
C120.86443 (9)0.35268 (6)0.81444 (4)0.01860 (16)
H12A0.8490 (14)0.2802 (10)0.8217 (7)0.040667
H12B0.9251 (14)0.3613 (11)0.7792 (7)0.042333
H12C0.7874 (14)0.3873 (12)0.8029 (7)0.045667
C131.01689 (9)0.34488 (7)0.88745 (6)0.0237 (2)
H13A1.0053 (14)0.2707 (11)0.8862 (8)0.045333
H13B1.0505 (15)0.3631 (12)0.9304 (9)0.048000
H13C1.0822 (16)0.3596 (12)0.8541 (8)0.051333
C140.78969 (7)0.47285 (5)0.63325 (3)0.01002 (12)
C150.82603 (7)0.42270 (6)0.58483 (3)0.01233 (13)
H15A0.8923 (12)0.4523 (10)0.5579 (6)0.027000
C160.78524 (7)0.33492 (6)0.57248 (4)0.01517 (15)
H16A0.8133 (13)0.2964 (10)0.5337 (6)0.035333
C170.70732 (8)0.29738 (6)0.61046 (4)0.01602 (14)
H17A0.6763 (13)0.2279 (10)0.6031 (7)0.038667
C180.67003 (7)0.34634 (6)0.65963 (4)0.01417 (14)
H18A0.6108 (13)0.3147 (10)0.6903 (7)0.033333
C190.70912 (7)0.43550 (5)0.67266 (3)0.01037 (12)
C200.60329 (7)0.44845 (6)0.76421 (3)0.01187 (13)
H20A0.6274 (12)0.3790 (9)0.7804 (6)0.026667
H20B0.5195 (10)0.4389 (9)0.7460 (7)0.026333
C210.53634 (7)0.45617 (6)0.88799 (4)0.01315 (14)
H21A0.4639 (11)0.4213 (10)0.8674 (6)0.025000
C220.48064 (7)0.60402 (6)0.80771 (4)0.01236 (13)
H22A0.4785 (12)0.6580 (9)0.8420 (6)0.025000
C230.61396 (8)0.38123 (7)0.91014 (4)0.02053 (18)
H23A0.5717 (14)0.3371 (11)0.9426 (7)0.042333
H23B0.6852 (14)0.4149 (11)0.9313 (7)0.042333
H23C0.6415 (13)0.3359 (11)0.8758 (7)0.041667
C240.49925 (8)0.51663 (7)0.93998 (4)0.01876 (17)
H24A0.4407 (14)0.5758 (12)0.9264 (7)0.036333
H24B0.5692 (13)0.5497 (11)0.9614 (6)0.035000
H24C0.4614 (13)0.4752 (11)0.9734 (7)0.038000
C250.49931 (7)0.64751 (6)0.74673 (5)0.01704 (14)
H25A0.4349 (12)0.6996 (10)0.7387 (7)0.035667
H25B0.4952 (12)0.5946 (11)0.7131 (7)0.035333
H25C0.5786 (13)0.6811 (10)0.7415 (7)0.036333
C260.36756 (7)0.55820 (7)0.80854 (4)0.01752 (16)
H26A0.3053 (12)0.6090 (10)0.7960 (7)0.036000
H26B0.3449 (12)0.5314 (11)0.8522 (7)0.037333
H26C0.3630 (12)0.5018 (11)0.7775 (6)0.034667
C270.77595 (6)0.64129 (5)0.62074 (3)0.01012 (13)
C280.74256 (8)0.64003 (6)0.56205 (4)0.01431 (14)
H28A0.7562 (13)0.5766 (10)0.5369 (6)0.029333
C290.69218 (8)0.71649 (6)0.53616 (4)0.01813 (16)
H29A0.6692 (14)0.7148 (10)0.4907 (6)0.038333
C300.67548 (8)0.79432 (6)0.57071 (4)0.01677 (16)
H30A0.6390 (14)0.8561 (10)0.5524 (6)0.036333
C310.70550 (7)0.79597 (5)0.63025 (3)0.01309 (13)
H31A0.6908 (13)0.8577 (9)0.6537 (6)0.029333
C320.75541 (7)0.71942 (5)0.65749 (3)0.00988 (12)
C330.74815 (7)0.78803 (5)0.75568 (4)0.01164 (12)
H33A0.6632 (10)0.8093 (9)0.7458 (7)0.026667
H33B0.7982 (11)0.8500 (8)0.7517 (7)0.028333
C340.62751 (7)0.80867 (5)0.86342 (4)0.01183 (13)
H34A0.5632 (11)0.7828 (10)0.8330 (6)0.026000
C350.86864 (7)0.82275 (6)0.86200 (4)0.01279 (13)
H35A0.8494 (12)0.8932 (9)0.8470 (6)0.028000
C360.63052 (7)0.91393 (6)0.85997 (4)0.01616 (14)
H36A0.6590 (13)0.9383 (10)0.8174 (6)0.036000
H36B0.6865 (13)0.9422 (10)0.8952 (7)0.037333
H36C0.5486 (13)0.9427 (10)0.8683 (7)0.036000
C370.59270 (8)0.77705 (7)0.92536 (4)0.01775 (16)
H37A0.5123 (13)0.8041 (11)0.9364 (7)0.036333
H37B0.6501 (13)0.8007 (10)0.9576 (7)0.032667
H37C0.5858 (13)0.7038 (11)0.9291 (6)0.036000
C380.97436 (7)0.78993 (7)0.83201 (4)0.01691 (15)
H38A1.0371 (13)0.8418 (11)0.8360 (8)0.041000
H38B0.9612 (13)0.7792 (11)0.7842 (7)0.042000
H38C1.0018 (13)0.7242 (11)0.8526 (7)0.036000
C390.88001 (8)0.82429 (7)0.92964 (4)0.01780 (16)
H39A0.9557 (15)0.8575 (12)0.9433 (7)0.043333
H39B0.8770 (13)0.7537 (12)0.9476 (7)0.040000
H39C0.8159 (15)0.8629 (11)0.9514 (7)0.038000
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.00830 (4)0.00808 (4)0.01113 (4)0.00033 (3)0.00037 (3)0.00003 (3)
H1A0.0460000.0390000.0240000.0100000.0030000.006000
H1B0.0490000.0330000.0230000.0020000.0010000.005000
In10.008364 (17)0.007714 (17)0.008460 (17)0.000107 (15)0.000162 (19)0.000133 (19)
P10.00994 (8)0.00943 (8)0.00829 (8)0.00074 (6)0.00068 (6)0.00063 (6)
P20.00855 (8)0.01072 (8)0.00868 (8)0.00177 (6)0.00046 (6)0.00032 (6)
P30.01089 (8)0.00767 (7)0.00853 (7)0.00017 (7)0.00057 (7)0.00087 (6)
N10.0095 (2)0.0137 (2)0.0093 (2)0.00094 (19)0.0002 (2)0.0011 (3)
N20.0118 (3)0.0116 (3)0.0105 (3)0.0022 (2)0.0014 (2)0.0027 (2)
N30.0142 (3)0.0091 (2)0.0085 (2)0.0015 (2)0.0007 (2)0.0000 (2)
N40.0103 (2)0.0087 (3)0.0073 (2)0.0009 (2)0.0007 (2)0.0001 (2)
C10.0101 (3)0.0100 (3)0.0084 (3)0.0004 (2)0.0012 (2)0.0002 (2)
C20.0142 (3)0.0134 (3)0.0105 (3)0.0001 (3)0.0024 (2)0.0007 (3)
H2A0.0270000.0390000.0180000.0000000.0020000.005000
C30.0148 (3)0.0158 (3)0.0132 (3)0.0010 (3)0.0044 (3)0.0012 (3)
H3A0.0290000.0450000.0220000.0050000.0090000.007000
C40.0114 (3)0.0153 (3)0.0157 (3)0.0008 (3)0.0036 (3)0.0006 (3)
H4A0.0170000.0410000.0330000.0040000.0040000.002000
C50.0099 (3)0.0148 (3)0.0124 (3)0.0002 (3)0.0007 (2)0.0005 (3)
H5A0.0200000.0400000.0230000.0000000.0030000.004000
C60.0095 (3)0.0108 (3)0.0091 (3)0.0008 (2)0.0011 (2)0.0001 (2)
C70.0101 (3)0.0144 (4)0.0099 (3)0.0014 (3)0.0003 (2)0.0008 (3)
H7A0.0260000.0310000.0270000.0090000.0010000.001000
H7B0.0240000.0340000.0290000.0130000.0010000.005000
C80.0159 (4)0.0164 (4)0.0104 (3)0.0014 (3)0.0020 (3)0.0003 (3)
H8A0.0340000.0190000.0300000.0010000.0040000.002000
C90.0149 (3)0.0106 (3)0.0159 (3)0.0014 (3)0.0006 (3)0.0025 (3)
H9A0.0330000.0240000.0300000.0010000.0100000.006000
C100.0167 (4)0.0292 (5)0.0209 (4)0.0006 (4)0.0078 (3)0.0034 (4)
H10A0.0310000.0460000.0720000.0130000.0090000.015000
H10B0.0280000.0890000.0380000.0130000.0010000.021000
H10C0.0310000.0610000.0320000.0040000.0110000.008000
C110.0340 (6)0.0353 (6)0.0120 (4)0.0098 (5)0.0003 (4)0.0006 (4)
H11A0.0590000.0470000.0200000.0140000.0070000.000000
H11B0.0290000.0710000.0390000.0090000.0100000.020000
H11C0.0630000.0230000.0340000.0020000.0020000.008000
C120.0242 (4)0.0114 (3)0.0202 (4)0.0006 (3)0.0017 (3)0.0018 (3)
H12A0.0570000.0160000.0490000.0030000.0050000.002000
H12B0.0380000.0320000.0570000.0090000.0210000.009000
H12C0.0520000.0520000.0330000.0120000.0150000.011000
C130.0203 (4)0.0144 (4)0.0364 (6)0.0055 (3)0.0056 (4)0.0050 (4)
H13A0.0490000.0190000.0680000.0090000.0100000.004000
H13B0.0270000.0440000.0730000.0110000.0080000.007000
H13C0.0580000.0440000.0520000.0180000.0270000.004000
C140.0121 (3)0.0091 (3)0.0088 (3)0.0011 (2)0.0001 (2)0.0014 (2)
C150.0153 (3)0.0117 (3)0.0101 (3)0.0002 (3)0.0012 (2)0.0022 (3)
H15A0.0280000.0290000.0240000.0010000.0090000.002000
C160.0187 (4)0.0131 (3)0.0137 (3)0.0007 (3)0.0009 (3)0.0060 (3)
H16A0.0410000.0340000.0310000.0010000.0090000.018000
C170.0184 (4)0.0125 (3)0.0172 (4)0.0028 (3)0.0008 (3)0.0056 (3)
H17A0.0460000.0260000.0440000.0140000.0070000.017000
C180.0144 (3)0.0124 (3)0.0158 (4)0.0031 (3)0.0016 (3)0.0041 (3)
H18A0.0370000.0300000.0330000.0150000.0110000.006000
C190.0106 (3)0.0101 (3)0.0104 (3)0.0007 (2)0.0002 (2)0.0024 (2)
C200.0111 (3)0.0124 (3)0.0121 (3)0.0028 (3)0.0014 (2)0.0020 (2)
H20A0.0320000.0180000.0300000.0000000.0050000.003000
H20B0.0180000.0350000.0260000.0060000.0020000.005000
C210.0131 (3)0.0156 (3)0.0108 (3)0.0038 (3)0.0009 (3)0.0012 (3)
H21A0.0230000.0270000.0250000.0080000.0010000.002000
C220.0097 (3)0.0155 (3)0.0119 (3)0.0004 (3)0.0002 (2)0.0020 (3)
H22A0.0280000.0230000.0240000.0000000.0010000.007000
C230.0205 (4)0.0223 (4)0.0189 (4)0.0001 (3)0.0022 (3)0.0076 (3)
H23A0.0450000.0380000.0440000.0020000.0110000.023000
H23B0.0530000.0380000.0360000.0180000.0070000.001000
H23C0.0310000.0490000.0450000.0010000.0120000.008000
C240.0240 (4)0.0220 (4)0.0103 (3)0.0059 (3)0.0030 (3)0.0014 (3)
H24A0.0470000.0340000.0280000.0130000.0020000.001000
H24B0.0450000.0360000.0240000.0100000.0120000.005000
H24C0.0350000.0510000.0280000.0170000.0000000.011000
C250.0169 (3)0.0189 (3)0.0153 (4)0.0028 (3)0.0010 (3)0.0018 (4)
H25A0.0330000.0380000.0360000.0140000.0010000.010000
H25B0.0250000.0440000.0370000.0090000.0000000.013000
H25C0.0540000.0340000.0210000.0000000.0000000.005000
C260.0106 (3)0.0233 (4)0.0186 (4)0.0014 (3)0.0011 (3)0.0036 (3)
H26A0.0210000.0380000.0490000.0060000.0050000.007000
H26B0.0310000.0390000.0420000.0080000.0010000.018000
H26C0.0270000.0490000.0280000.0070000.0040000.008000
C270.0132 (3)0.0094 (3)0.0078 (3)0.0014 (2)0.0007 (2)0.0000 (2)
C280.0204 (4)0.0131 (3)0.0094 (3)0.0043 (3)0.0032 (3)0.0013 (2)
H28A0.0430000.0240000.0210000.0100000.0030000.006000
C290.0268 (4)0.0171 (4)0.0105 (3)0.0086 (3)0.0056 (3)0.0006 (3)
H29A0.0620000.0350000.0180000.0160000.0110000.000000
C300.0240 (4)0.0153 (4)0.0111 (3)0.0084 (3)0.0028 (3)0.0011 (3)
H30A0.0570000.0250000.0270000.0180000.0060000.006000
C310.0173 (3)0.0115 (3)0.0105 (3)0.0048 (3)0.0010 (3)0.0006 (2)
H31A0.0440000.0180000.0260000.0090000.0020000.003000
C320.0123 (3)0.0086 (3)0.0088 (3)0.0015 (3)0.0009 (2)0.0001 (2)
C330.0162 (3)0.0087 (2)0.0101 (3)0.0013 (2)0.0001 (3)0.0004 (2)
H33A0.0260000.0280000.0260000.0110000.0020000.002000
H33B0.0390000.0170000.0290000.0070000.0020000.000000
C340.0137 (3)0.0112 (3)0.0106 (3)0.0013 (2)0.0006 (3)0.0010 (3)
H34A0.0230000.0290000.0260000.0000000.0050000.005000
C350.0144 (3)0.0108 (3)0.0133 (3)0.0023 (3)0.0006 (3)0.0015 (3)
H35A0.0330000.0170000.0340000.0020000.0020000.000000
C360.0206 (4)0.0116 (3)0.0162 (3)0.0035 (3)0.0009 (3)0.0008 (3)
H36A0.0520000.0280000.0280000.0030000.0100000.006000
H36B0.0340000.0280000.0500000.0120000.0090000.000000
H36C0.0470000.0240000.0370000.0040000.0080000.007000
C370.0221 (4)0.0176 (4)0.0136 (4)0.0014 (3)0.0036 (3)0.0004 (3)
H37A0.0330000.0380000.0380000.0120000.0140000.002000
H37B0.0420000.0190000.0370000.0020000.0090000.001000
H37C0.0430000.0420000.0230000.0090000.0040000.001000
C380.0146 (4)0.0182 (4)0.0179 (4)0.0040 (3)0.0011 (3)0.0027 (3)
H38A0.0270000.0440000.0520000.0160000.0050000.011000
H38B0.0390000.0380000.0490000.0140000.0090000.016000
H38C0.0330000.0510000.0240000.0010000.0010000.007000
C390.0190 (4)0.0203 (4)0.0142 (4)0.0029 (3)0.0026 (3)0.0041 (3)
H39A0.0350000.0600000.0350000.0210000.0070000.009000
H39B0.0400000.0480000.0320000.0060000.0040000.013000
H39C0.0510000.0340000.0290000.0030000.0050000.005000
Geometric parameters (Å, º) top
Ni1—H1A1.660 (16)C14—C191.4330 (11)
Ni1—H1B1.680 (16)C15—H15A1.099 (14)
Ni1—In12.4787 (1)C15—C161.3982 (12)
Ni1—P12.2832 (2)C16—H16A1.094 (14)
Ni1—P22.2528 (2)C16—C171.3920 (13)
Ni1—P32.2502 (2)C17—H17A1.091 (14)
H1A—H1B0.98 (2)C17—C181.3945 (12)
In1—N12.1114 (6)C18—H18A1.101 (14)
In1—N22.1231 (7)C18—C191.4124 (11)
In1—N32.1141 (7)C20—H20A1.113 (14)
In1—N42.3681 (7)C20—H20B1.112 (12)
P1—C71.8649 (9)C21—H21A1.120 (13)
P1—C81.8706 (9)C21—C231.5283 (13)
P1—C91.8648 (8)C21—C241.5342 (13)
P2—C201.8728 (8)C22—H22A1.103 (13)
P2—C211.8587 (8)C22—C251.5312 (14)
P2—C221.8786 (8)C22—C261.5334 (12)
P3—C331.8882 (8)C23—H23A1.102 (15)
P3—C341.8678 (8)C23—H23B1.107 (18)
P3—C351.8553 (8)C23—H23C1.072 (17)
N1—C61.3643 (11)C24—H24A1.160 (16)
N1—C71.4437 (11)C24—H24B1.093 (16)
N2—C191.3668 (10)C24—H24C1.071 (16)
N2—C201.4457 (10)C25—H25A1.107 (13)
N3—C321.3708 (10)C25—H25B1.081 (16)
N3—C331.4410 (10)C25—H25C1.090 (15)
N4—C11.4633 (10)C26—H26A1.096 (14)
N4—C141.4569 (10)C26—H26B1.094 (16)
N4—C271.4611 (10)C26—H26C1.079 (16)
C1—C21.3876 (11)C27—C281.3854 (11)
C1—C61.4307 (11)C27—C321.4285 (11)
C2—H2A1.061 (13)C28—H28A1.096 (13)
C2—C31.4000 (12)C28—C291.3985 (12)
C3—H3A1.073 (13)C29—H29A1.063 (14)
C3—C41.3947 (12)C29—C301.3890 (13)
C4—H4A1.091 (13)C30—H30A1.084 (14)
C4—C51.3927 (11)C30—C311.3925 (12)
C5—H5A1.097 (13)C31—H31A1.057 (13)
C5—C61.4133 (11)C31—C321.4101 (11)
C7—H7A1.106 (14)C33—H33A1.106 (12)
C7—H7B1.108 (14)C33—H33B1.093 (12)
C8—H8A1.105 (14)C34—H34A1.109 (13)
C8—C101.5350 (13)C34—C361.5328 (12)
C8—C111.5311 (14)C34—C371.5313 (12)
C9—H9A1.116 (14)C35—H35A1.104 (13)
C9—C121.5328 (13)C35—C381.5340 (13)
C9—C131.5276 (13)C35—C391.5324 (13)
C10—H10A1.090 (16)C36—H36A1.081 (14)
C10—H10B1.116 (17)C36—H36B1.125 (17)
C10—H10C1.110 (17)C36—H36C1.101 (16)
C11—H11A1.080 (15)C37—H37A1.086 (15)
C11—H11B1.101 (18)C37—H37B1.067 (16)
C11—H11C1.035 (17)C37—H37C1.072 (16)
C12—H12A1.083 (14)C38—H38A1.080 (15)
C12—H12B1.094 (18)C38—H38B1.102 (17)
C12—H12C1.099 (18)C38—H38C1.115 (16)
C13—H13A1.088 (15)C39—H39A1.087 (16)
C13—H13B1.09 (2)C39—H39B1.105 (18)
C13—H13C1.12 (2)C39—H39C1.081 (17)
C14—C151.3864 (11)
H1B—Ni1—H1A34.2 (7)C15—C14—N4121.39 (7)
In1—Ni1—H1A160.4 (6)C19—C14—N4117.96 (6)
In1—Ni1—H1B162.3 (7)C19—C14—C15120.62 (7)
P1—Ni1—H1A88.9 (6)H15A—C15—C14117.7 (7)
P1—Ni1—H1B93.6 (7)C16—C15—C14121.54 (8)
P1—Ni1—In181.143 (6)C16—C15—H15A120.6 (7)
P2—Ni1—H1A89.0 (6)H16A—C16—C15121.0 (8)
P2—Ni1—H1B114.2 (7)C17—C16—C15118.61 (7)
P2—Ni1—In182.401 (6)C17—C16—H16A120.4 (8)
P2—Ni1—P1122.762 (8)H17A—C17—C16120.5 (8)
P3—Ni1—H1A115.0 (6)C18—C17—C16120.85 (8)
P3—Ni1—H1B83.5 (6)C18—C17—H17A118.6 (8)
P3—Ni1—In184.563 (6)H18A—C18—C17120.1 (8)
P3—Ni1—P1120.211 (9)C19—C18—C17121.58 (8)
P3—Ni1—P2112.153 (9)C19—C18—H18A118.3 (8)
H1B—H1A—Ni174.0 (16)C14—C19—N2118.77 (7)
H1A—H1B—Ni171.8 (15)C18—C19—N2124.42 (7)
N1—In1—Ni1104.66 (2)C18—C19—C14116.80 (7)
N2—In1—Ni1102.740 (18)N2—C20—P2108.29 (5)
N2—In1—N1116.48 (3)H20A—C20—P2108.3 (7)
N3—In1—Ni1103.277 (18)H20A—C20—N2114.2 (7)
N3—In1—N1111.74 (3)H20B—C20—P2110.0 (7)
N3—In1—N2115.83 (3)H20B—C20—N2111.4 (8)
N4—In1—Ni1178.627 (16)H20B—C20—H20A104.5 (10)
N4—In1—N176.59 (3)H21A—C21—P2106.6 (7)
N4—In1—N276.12 (2)C23—C21—P2112.44 (6)
N4—In1—N376.66 (2)C23—C21—H21A107.6 (8)
C7—P1—Ni1117.47 (3)C24—C21—P2110.05 (6)
C8—P1—Ni1110.57 (3)C24—C21—H21A110.1 (7)
C8—P1—C7103.32 (4)C24—C21—C23109.97 (8)
C9—P1—Ni1116.57 (3)H22A—C22—P2104.7 (7)
C9—P1—C7102.06 (4)C25—C22—P2110.99 (6)
C9—P1—C8105.36 (4)C25—C22—H22A109.9 (7)
C20—P2—Ni1117.98 (3)C26—C22—P2115.87 (6)
C21—P2—Ni1114.43 (3)C26—C22—H22A106.3 (7)
C21—P2—C20102.58 (4)C26—C22—C25108.94 (7)
C22—P2—Ni1117.37 (3)H23A—C23—C21110.0 (9)
C22—P2—C20100.54 (4)H23B—C23—C21108.3 (8)
C22—P2—C21101.40 (4)H23B—C23—H23A109.8 (12)
C33—P3—Ni1118.84 (2)H23C—C23—C21113.4 (8)
C34—P3—Ni1112.79 (3)H23C—C23—H23A105.6 (12)
C34—P3—C3399.09 (4)H23C—C23—H23B109.8 (11)
C35—P3—Ni1118.85 (3)H24A—C24—C21113.9 (8)
C35—P3—C3399.58 (4)H24B—C24—C21111.1 (8)
C35—P3—C34104.91 (4)H24B—C24—H24A105.8 (12)
C6—N1—In1113.00 (5)H24C—C24—C21110.1 (8)
C7—N1—In1115.69 (5)H24C—C24—H24A109.7 (12)
C7—N1—C6119.47 (6)H24C—C24—H24B105.9 (11)
C19—N2—In1112.98 (5)H25A—C25—C22108.9 (8)
C20—N2—In1118.06 (5)H25B—C25—C22109.2 (8)
C20—N2—C19120.63 (7)H25B—C25—H25A109.8 (11)
C32—N3—In1113.14 (5)H25C—C25—C22114.4 (8)
C33—N3—In1118.70 (5)H25C—C25—H25A107.9 (11)
C33—N3—C32119.67 (6)H25C—C25—H25B106.5 (11)
C1—N4—In1103.16 (5)H26A—C26—C22109.2 (8)
C14—N4—In1103.42 (4)H26B—C26—C22113.2 (8)
C14—N4—C1115.80 (6)H26B—C26—H26A107.3 (11)
C27—N4—In1102.68 (4)H26C—C26—C22111.6 (8)
C27—N4—C1113.54 (6)H26C—C26—H26A108.0 (11)
C27—N4—C14115.74 (6)H26C—C26—H26B107.4 (11)
C2—C1—N4121.39 (7)C28—C27—N4121.17 (7)
C6—C1—N4117.98 (7)C32—C27—N4117.94 (6)
C6—C1—C2120.56 (7)C32—C27—C28120.89 (7)
H2A—C2—C1118.5 (8)H28A—C28—C27117.5 (7)
C3—C2—C1121.47 (8)C29—C28—C27121.21 (8)
C3—C2—H2A120.0 (8)C29—C28—H28A121.3 (7)
H3A—C3—C2122.3 (8)H29A—C29—C28120.0 (8)
C4—C3—C2118.65 (7)C30—C29—C28118.55 (8)
C4—C3—H3A119.0 (8)C30—C29—H29A121.4 (8)
H4A—C4—C3119.0 (7)H30A—C30—C29121.4 (8)
C5—C4—C3120.74 (7)C31—C30—C29121.11 (8)
C5—C4—H4A120.2 (8)C31—C30—H30A117.5 (8)
H5A—C5—C4119.1 (7)H31A—C31—C30116.9 (7)
C6—C5—C4121.60 (8)C32—C31—C30121.37 (7)
C6—C5—H5A119.3 (7)C32—C31—H31A121.7 (7)
C1—C6—N1119.13 (7)C27—C32—N3119.29 (7)
C5—C6—N1123.89 (8)C31—C32—N3123.92 (7)
C5—C6—C1116.98 (7)C31—C32—C27116.79 (7)
N1—C7—P1108.68 (6)N3—C33—P3111.65 (5)
H7A—C7—P1106.3 (7)H33A—C33—P3107.9 (8)
H7A—C7—N1115.1 (7)H33A—C33—N3111.4 (7)
H7B—C7—P1109.5 (7)H33B—C33—P3107.4 (8)
H7B—C7—N1111.0 (7)H33B—C33—N3112.0 (7)
H7B—C7—H7A106.1 (11)H33B—C33—H33A106.1 (10)
H8A—C8—P1103.7 (8)H34A—C34—P3102.8 (7)
C10—C8—P1117.17 (7)C36—C34—P3114.74 (6)
C10—C8—H8A106.5 (8)C36—C34—H34A109.0 (7)
C11—C8—P1110.50 (7)C37—C34—P3113.44 (6)
C11—C8—H8A106.8 (8)C37—C34—H34A105.4 (7)
C11—C8—C10111.25 (8)C37—C34—C36110.66 (7)
H9A—C9—P1104.6 (7)H35A—C35—P3105.6 (8)
C12—C9—P1109.99 (6)C38—C35—P3108.60 (6)
C12—C9—H9A107.7 (8)C38—C35—H35A109.4 (8)
C13—C9—P1116.67 (6)C39—C35—P3113.31 (6)
C13—C9—H9A108.7 (8)C39—C35—H35A108.1 (7)
C13—C9—C12108.81 (8)C39—C35—C38111.56 (7)
H10A—C10—C8112.4 (9)H36A—C36—C34112.3 (8)
H10B—C10—C8109.5 (9)H36B—C36—C34110.1 (8)
H10B—C10—H10A108.4 (14)H36B—C36—H36A108.1 (11)
H10C—C10—C8112.4 (8)H36C—C36—C34110.5 (8)
H10C—C10—H10A105.8 (13)H36C—C36—H36A108.7 (12)
H10C—C10—H10B108.3 (12)H36C—C36—H36B107.0 (11)
H11A—C11—C8109.7 (9)H37A—C37—C34110.5 (8)
H11B—C11—C8113.2 (8)H37B—C37—C34110.0 (8)
H11B—C11—H11A109.8 (13)H37B—C37—H37A108.7 (12)
H11C—C11—C8111.6 (8)H37C—C37—C34113.0 (8)
H11C—C11—H11A103.8 (13)H37C—C37—H37A105.7 (12)
H11C—C11—H11B108.4 (12)H37C—C37—H37B108.6 (11)
H12A—C12—C9109.0 (9)H38A—C38—C35110.1 (9)
H12B—C12—C9108.3 (8)H38B—C38—C35110.7 (8)
H12B—C12—H12A109.8 (12)H38B—C38—H38A106.4 (12)
H12C—C12—C9109.4 (8)H38C—C38—C35109.6 (8)
H12C—C12—H12A109.4 (12)H38C—C38—H38A110.6 (12)
H12C—C12—H12B110.8 (11)H38C—C38—H38B109.4 (11)
H13A—C13—C9110.6 (9)H39A—C39—C35111.5 (9)
H13B—C13—C9114.6 (9)H39B—C39—C35110.4 (8)
H13B—C13—H13A108.3 (13)H39B—C39—H39A109.7 (13)
H13C—C13—C9110.9 (8)H39C—C39—C35113.2 (8)
H13C—C13—H13A105.4 (13)H39C—C39—H39A104.8 (12)
H13C—C13—H13B106.6 (13)H39C—C39—H39B106.9 (11)
In1—N1—C6—C126.71 (6)N2—C19—C18—C17179.40 (8)
In1—N1—C6—C5152.14 (5)N3—C32—C27—N44.20 (9)
In1—N1—C7—P129.24 (4)N3—C32—C27—C28176.48 (8)
In1—N2—C19—C1426.58 (6)N3—C32—C31—C30178.37 (9)
In1—N2—C19—C18152.20 (6)N4—C1—C2—C3177.50 (7)
In1—N2—C20—P223.16 (5)N4—C1—C6—C5176.83 (7)
In1—N3—C32—C2722.26 (6)N4—C14—C15—C16178.54 (7)
In1—N3—C32—C31157.58 (6)N4—C14—C19—C18177.91 (7)
In1—N3—C33—P314.20 (5)N4—C27—C28—C29176.42 (8)
In1—N4—C1—C2157.34 (5)N4—C27—C32—C31175.95 (7)
In1—N4—C1—C619.55 (5)C1—C2—C3—C41.10 (10)
In1—N4—C14—C15157.03 (5)C1—C6—C5—C40.45 (9)
In1—N4—C14—C1921.07 (5)C2—C3—C4—C50.73 (10)
In1—N4—C27—C28156.69 (5)C3—C4—C5—C60.04 (10)
In1—N4—C27—C3224.00 (5)C14—C15—C16—C170.78 (10)
P1—C7—N1—C6169.58 (5)C14—C19—C18—C170.60 (9)
P2—C20—N2—C19169.24 (5)C15—C16—C17—C180.40 (10)
P3—C33—N3—C32160.05 (6)C16—C17—C18—C190.30 (11)
N1—C6—C1—N42.11 (8)C27—C28—C29—C300.33 (11)
N1—C6—C1—C2179.03 (7)C27—C32—C31—C301.47 (10)
N1—C6—C5—C4179.33 (8)C28—C29—C30—C311.60 (12)
N2—C19—C14—N40.96 (8)C29—C30—C31—C320.99 (12)
N2—C19—C14—C15179.08 (7)
(GOJNIF_HAR_NoMoRe) top
Crystal data top
C39H62InN4NiP3Dx = 1.415 Mg m3
Mr = 853.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9537 reflections
a = 12.2127 (4) Åθ = 2.3–36.4°
b = 14.5402 (5) ŵ = 1.20 mm1
c = 22.5601 (8) ÅT = 100 K
V = 4006.1 (2) Å3Block, gold
Z = 40.14 × 0.08 × 0.06 mm
F(000) = 1784.150
Data collection top
Bruker Photon-II CMOS
diffractometer
18741 reflections with I 2u(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
SADABS. R.Blessing, 1995
θmax = 36.4°, θmin = 2.3°
Tmin = 0.701, Tmax = 0.747h = 2020
237431 measured reflectionsk = 2424
19473 independent reflectionsl = 3737
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullOnly H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.016 w = 1/[σ2(Fo2) + (0.0239P)2 + 0.5897P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.040(Δ/σ)max = 0.001
S = 0.96Δρmax = 0.34 e Å3
19473 reflectionsΔρmin = 0.55 e Å3
619 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
0 restraintsAbsolute structure parameter: 0.003 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.755816 (9)0.598650 (7)0.856150 (5)0.009304 (19)
H1A0.7315 (18)0.5702 (15)0.9260 (9)0.037000
H1B0.753 (2)0.6337 (15)0.9273 (9)0.035333
In10.798239 (4)0.580829 (3)0.749322 (3)0.008315 (11)
P10.918454 (18)0.522248 (15)0.864338 (9)0.00934 (3)
P20.599028 (18)0.528565 (15)0.829176 (10)0.00942 (3)
P30.753619 (19)0.750093 (15)0.835678 (9)0.00916 (3)
N10.96176 (5)0.53381 (5)0.74727 (4)0.01093 (10)
N20.67666 (6)0.48666 (5)0.72035 (3)0.01136 (12)
N30.78427 (6)0.71632 (5)0.71619 (3)0.01066 (11)
N40.83415 (6)0.56338 (5)0.64679 (3)0.00883 (11)
C10.95346 (6)0.57171 (5)0.64336 (4)0.00957 (12)
C21.00523 (7)0.59713 (6)0.59110 (4)0.01287 (14)
H2A0.9573 (14)0.6117 (12)0.5540 (6)0.028333
C31.11901 (8)0.60861 (6)0.58831 (4)0.01475 (15)
H3A1.1608 (15)0.6284 (13)0.5481 (7)0.032000
C41.18035 (7)0.59547 (6)0.63979 (4)0.01430 (14)
H4A1.2684 (13)0.6058 (12)0.6377 (8)0.030333
C51.12982 (7)0.57046 (6)0.69273 (4)0.01248 (14)
H5A1.1801 (13)0.5630 (12)0.7329 (7)0.028000
C61.01531 (7)0.55739 (6)0.69640 (4)0.00990 (13)
C71.01947 (7)0.53661 (6)0.80306 (4)0.01156 (14)
H7A1.0634 (14)0.6011 (12)0.8127 (7)0.028000
H7B1.0828 (14)0.4829 (12)0.8052 (7)0.029000
C80.99543 (8)0.56223 (7)0.93121 (4)0.01429 (15)
H8A0.9801 (15)0.6381 (12)0.9321 (7)0.027667
C90.91080 (8)0.39463 (6)0.87150 (4)0.01393 (14)
H9A0.8502 (15)0.3832 (11)0.9078 (7)0.029667
C101.12038 (9)0.55058 (9)0.93051 (5)0.02237 (19)
H10A1.1454 (16)0.4783 (14)0.9261 (10)0.050333
H10B1.1554 (16)0.5768 (17)0.9739 (9)0.051667
H10C1.1603 (15)0.5854 (15)0.8926 (8)0.041667
C110.94552 (11)0.52155 (10)0.98768 (5)0.0270 (2)
H11A0.9871 (17)0.5546 (14)1.0255 (8)0.042000
H11B0.9561 (16)0.4456 (15)0.9906 (9)0.046667
H11C0.8635 (17)0.5359 (12)0.9916 (8)0.040000
C120.86444 (9)0.35268 (7)0.81443 (5)0.01864 (17)
H12A0.8484 (17)0.2809 (11)0.8223 (9)0.041333
H12B0.9250 (17)0.3606 (13)0.7799 (9)0.043000
H12C0.7863 (17)0.3887 (14)0.8039 (8)0.046000
C131.01684 (10)0.34490 (7)0.88744 (6)0.0237 (2)
H13A1.0056 (17)0.2705 (12)0.8869 (9)0.045667
H13B1.0515 (17)0.3624 (15)0.9296 (10)0.048333
H13C1.0830 (19)0.3608 (14)0.8551 (9)0.051667
C140.78963 (7)0.47286 (5)0.63325 (3)0.01011 (12)
C150.82600 (7)0.42271 (6)0.58483 (4)0.01240 (13)
H15A0.8929 (14)0.4529 (12)0.5581 (7)0.027333
C160.78525 (8)0.33492 (6)0.57248 (4)0.01526 (15)
H16A0.8119 (16)0.2970 (13)0.5323 (8)0.036000
C170.70728 (8)0.29739 (6)0.61048 (4)0.01609 (15)
H17A0.6752 (16)0.2269 (12)0.6027 (8)0.039333
C180.67007 (8)0.34633 (6)0.65965 (4)0.01425 (15)
H18A0.6109 (15)0.3151 (12)0.6902 (8)0.034000
C190.70913 (7)0.43549 (5)0.67266 (4)0.01043 (12)
C200.60325 (7)0.44845 (6)0.76424 (4)0.01194 (14)
H20A0.6269 (14)0.3788 (11)0.7808 (7)0.027000
H20B0.5199 (12)0.4394 (11)0.7455 (7)0.027000
C210.53633 (7)0.45619 (6)0.88799 (4)0.01321 (14)
H21A0.4653 (13)0.4218 (12)0.8680 (7)0.025000
C220.48066 (7)0.60401 (6)0.80770 (4)0.01243 (13)
H22A0.4783 (14)0.6577 (11)0.8418 (7)0.025333
C230.61403 (9)0.38122 (8)0.91014 (5)0.02053 (18)
H23A0.5723 (17)0.3376 (13)0.9429 (9)0.043000
H23B0.6857 (17)0.4150 (14)0.9322 (9)0.042667
H23C0.6414 (15)0.3353 (14)0.8759 (9)0.042333
C240.49921 (9)0.51666 (8)0.93998 (4)0.01882 (17)
H24A0.4395 (17)0.5763 (14)0.9255 (8)0.036667
H24B0.5685 (16)0.5499 (13)0.9612 (7)0.035333
H24C0.4609 (16)0.4765 (13)0.9738 (8)0.038333
C250.49929 (8)0.64748 (7)0.74674 (5)0.01718 (15)
H25A0.4347 (14)0.6998 (12)0.7385 (8)0.036000
H25B0.4947 (14)0.5934 (13)0.7135 (8)0.035667
H25C0.5788 (16)0.6802 (12)0.7410 (7)0.036667
C260.36760 (8)0.55818 (7)0.80853 (5)0.01755 (17)
H26A0.3048 (14)0.6098 (13)0.7978 (8)0.036667
H26B0.3438 (15)0.5299 (13)0.8521 (8)0.037667
H26C0.3631 (14)0.5020 (13)0.7779 (7)0.035333
C270.77588 (7)0.64129 (6)0.62077 (4)0.01021 (13)
C280.74258 (8)0.64005 (6)0.56207 (4)0.01443 (14)
H28A0.7556 (16)0.5753 (11)0.5375 (7)0.029333
C290.69218 (9)0.71653 (7)0.53615 (4)0.01817 (17)
H29A0.6692 (16)0.7140 (12)0.4909 (7)0.038333
C300.67553 (8)0.79432 (7)0.57069 (4)0.01690 (16)
H30A0.6396 (17)0.8561 (12)0.5519 (8)0.036667
C310.70552 (8)0.79596 (6)0.63024 (4)0.01321 (13)
H31A0.6910 (15)0.8575 (10)0.6524 (7)0.029333
C320.75544 (7)0.71940 (6)0.65748 (3)0.01000 (12)
C330.74812 (7)0.78800 (5)0.75566 (4)0.01175 (12)
H33A0.6623 (13)0.8085 (11)0.7459 (7)0.027333
H33B0.7982 (12)0.8493 (10)0.7518 (7)0.028667
C340.62755 (7)0.80867 (6)0.86343 (4)0.01191 (13)
H34A0.5639 (13)0.7830 (11)0.8333 (7)0.026000
C350.86864 (7)0.82277 (6)0.86198 (4)0.01293 (14)
H35A0.8485 (15)0.8925 (11)0.8472 (7)0.028333
C360.63049 (8)0.91393 (6)0.85998 (4)0.01625 (15)
H36A0.6582 (16)0.9379 (12)0.8189 (8)0.036333
H36B0.6860 (16)0.9435 (13)0.8956 (9)0.037667
H36C0.5478 (16)0.9421 (12)0.8686 (8)0.036000
C370.59270 (9)0.77704 (7)0.92539 (4)0.01787 (16)
H37A0.5123 (15)0.8045 (14)0.9364 (8)0.036667
H37B0.6498 (15)0.8009 (12)0.9568 (8)0.032667
H37C0.5859 (15)0.7045 (13)0.9295 (7)0.036000
C380.97440 (8)0.78990 (7)0.83201 (5)0.01697 (16)
H38A1.0371 (15)0.8411 (13)0.8362 (9)0.041000
H38B0.9616 (16)0.7800 (13)0.7837 (9)0.041667
H38C1.0007 (15)0.7238 (13)0.8528 (8)0.035667
C390.88002 (9)0.82427 (7)0.92964 (4)0.01793 (17)
H39A0.9530 (17)0.8583 (15)0.9448 (8)0.043667
H39B0.8752 (16)0.7534 (14)0.9474 (8)0.040000
H39C0.8164 (18)0.8630 (13)0.9515 (8)0.038000
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.00845 (4)0.00819 (4)0.01127 (4)0.00035 (3)0.00037 (3)0.00002 (3)
H1A0.0470000.0400000.0240000.0100000.0030000.006000
H1B0.0490000.0340000.0230000.0020000.0010000.005000
In10.008502 (19)0.007840 (19)0.008604 (19)0.000102 (15)0.000154 (19)0.000134 (19)
P10.01006 (8)0.00953 (8)0.00843 (8)0.00075 (7)0.00069 (6)0.00060 (6)
P20.00865 (8)0.01082 (8)0.00878 (8)0.00176 (7)0.00046 (6)0.00029 (7)
P30.01105 (8)0.00777 (7)0.00865 (8)0.00019 (7)0.00055 (7)0.00086 (6)
N10.0095 (2)0.0137 (3)0.0095 (3)0.0010 (2)0.0002 (2)0.0012 (3)
N20.0119 (3)0.0117 (3)0.0105 (3)0.0022 (2)0.0012 (2)0.0027 (2)
N30.0144 (3)0.0091 (3)0.0086 (3)0.0015 (2)0.0008 (2)0.0001 (2)
N40.0105 (3)0.0088 (3)0.0072 (3)0.0009 (2)0.0008 (2)0.0001 (2)
C10.0102 (3)0.0101 (3)0.0084 (3)0.0004 (2)0.0012 (2)0.0003 (2)
C20.0143 (3)0.0135 (3)0.0107 (3)0.0002 (3)0.0025 (3)0.0007 (3)
H2A0.0270000.0400000.0180000.0000000.0020000.005000
C30.0150 (4)0.0159 (4)0.0133 (3)0.0011 (3)0.0044 (3)0.0011 (3)
H3A0.0290000.0450000.0220000.0040000.0090000.007000
C40.0114 (3)0.0155 (3)0.0160 (4)0.0008 (3)0.0036 (3)0.0006 (3)
H4A0.0170000.0410000.0330000.0040000.0040000.002000
C50.0100 (3)0.0150 (3)0.0125 (3)0.0002 (3)0.0008 (3)0.0007 (3)
H5A0.0210000.0400000.0230000.0000000.0030000.004000
C60.0097 (3)0.0109 (3)0.0092 (3)0.0007 (2)0.0011 (2)0.0001 (2)
C70.0102 (3)0.0144 (4)0.0101 (3)0.0013 (3)0.0003 (2)0.0008 (3)
H7A0.0260000.0310000.0270000.0090000.0010000.001000
H7B0.0240000.0340000.0290000.0130000.0010000.006000
C80.0159 (4)0.0164 (4)0.0105 (3)0.0014 (3)0.0020 (3)0.0003 (3)
H8A0.0340000.0190000.0300000.0010000.0040000.002000
C90.0151 (3)0.0107 (3)0.0160 (4)0.0014 (3)0.0006 (3)0.0026 (3)
H9A0.0340000.0240000.0310000.0010000.0100000.007000
C100.0167 (4)0.0294 (5)0.0210 (5)0.0005 (4)0.0078 (3)0.0034 (4)
H10A0.0320000.0460000.0730000.0130000.0090000.015000
H10B0.0280000.0890000.0380000.0130000.0010000.021000
H10C0.0320000.0610000.0320000.0040000.0110000.008000
C110.0337 (6)0.0352 (6)0.0120 (4)0.0098 (5)0.0003 (4)0.0008 (4)
H11A0.0590000.0470000.0200000.0140000.0070000.000000
H11B0.0290000.0710000.0400000.0090000.0100000.020000
H11C0.0630000.0230000.0340000.0020000.0020000.008000
C120.0244 (5)0.0116 (3)0.0199 (4)0.0006 (3)0.0017 (3)0.0018 (3)
H12A0.0580000.0160000.0500000.0030000.0040000.001000
H12B0.0390000.0320000.0580000.0090000.0210000.009000
H12C0.0530000.0520000.0330000.0120000.0150000.010000
C130.0202 (4)0.0145 (4)0.0365 (6)0.0054 (3)0.0056 (4)0.0050 (4)
H13A0.0500000.0190000.0680000.0090000.0100000.004000
H13B0.0280000.0440000.0730000.0120000.0080000.007000
H13C0.0590000.0440000.0520000.0180000.0270000.003000
C140.0124 (3)0.0090 (3)0.0089 (3)0.0012 (3)0.0000 (2)0.0015 (2)
C150.0153 (3)0.0118 (3)0.0101 (3)0.0000 (3)0.0011 (2)0.0022 (3)
H15A0.0290000.0290000.0240000.0010000.0090000.002000
C160.0189 (4)0.0132 (3)0.0137 (3)0.0006 (3)0.0009 (3)0.0059 (3)
H16A0.0420000.0340000.0320000.0010000.0090000.019000
C170.0184 (4)0.0126 (3)0.0172 (4)0.0028 (3)0.0007 (3)0.0055 (3)
H17A0.0470000.0260000.0450000.0140000.0070000.017000
C180.0145 (3)0.0123 (3)0.0160 (4)0.0030 (3)0.0015 (3)0.0041 (3)
H18A0.0380000.0300000.0340000.0150000.0110000.006000
C190.0107 (3)0.0102 (3)0.0104 (3)0.0006 (2)0.0002 (2)0.0024 (2)
C200.0111 (3)0.0126 (3)0.0121 (3)0.0029 (3)0.0015 (2)0.0018 (2)
H20A0.0330000.0180000.0300000.0010000.0050000.003000
H20B0.0190000.0360000.0260000.0060000.0020000.005000
C210.0132 (3)0.0156 (4)0.0108 (3)0.0037 (3)0.0008 (3)0.0012 (3)
H21A0.0230000.0270000.0250000.0080000.0010000.002000
C220.0097 (3)0.0156 (3)0.0119 (3)0.0004 (3)0.0003 (2)0.0020 (3)
H22A0.0280000.0240000.0240000.0000000.0010000.007000
C230.0206 (4)0.0223 (4)0.0187 (4)0.0001 (4)0.0024 (3)0.0075 (3)
H23A0.0450000.0390000.0450000.0010000.0110000.023000
H23B0.0530000.0390000.0360000.0180000.0070000.001000
H23C0.0320000.0500000.0450000.0010000.0120000.008000
C240.0241 (5)0.0221 (4)0.0102 (4)0.0059 (4)0.0031 (3)0.0015 (3)
H24A0.0470000.0350000.0280000.0130000.0020000.001000
H24B0.0450000.0370000.0240000.0100000.0120000.005000
H24C0.0350000.0520000.0280000.0180000.0000000.011000
C250.0170 (3)0.0191 (3)0.0155 (4)0.0028 (3)0.0011 (3)0.0020 (4)
H25A0.0330000.0390000.0360000.0140000.0010000.010000
H25B0.0250000.0450000.0370000.0090000.0000000.013000
H25C0.0540000.0350000.0210000.0000000.0000000.005000
C260.0107 (3)0.0232 (4)0.0188 (4)0.0015 (3)0.0011 (3)0.0035 (3)
H26A0.0210000.0400000.0490000.0050000.0050000.006000
H26B0.0310000.0400000.0420000.0080000.0010000.019000
H26C0.0280000.0500000.0280000.0080000.0040000.008000
C270.0134 (3)0.0094 (3)0.0078 (3)0.0014 (2)0.0006 (2)0.0000 (2)
C280.0206 (4)0.0130 (3)0.0096 (3)0.0041 (3)0.0030 (3)0.0013 (3)
H28A0.0430000.0240000.0210000.0100000.0030000.006000
C290.0269 (5)0.0170 (4)0.0106 (3)0.0085 (3)0.0056 (3)0.0007 (3)
H29A0.0620000.0350000.0180000.0150000.0120000.000000
C300.0242 (4)0.0153 (4)0.0111 (3)0.0084 (3)0.0029 (3)0.0012 (3)
H30A0.0570000.0260000.0270000.0180000.0070000.006000
C310.0175 (3)0.0116 (3)0.0105 (3)0.0048 (3)0.0011 (3)0.0006 (2)
H31A0.0440000.0180000.0260000.0090000.0020000.003000
C320.0123 (3)0.0087 (3)0.0090 (3)0.0015 (3)0.0009 (3)0.0002 (2)
C330.0163 (3)0.0087 (3)0.0103 (3)0.0012 (3)0.0000 (3)0.0005 (2)
H33A0.0270000.0290000.0260000.0110000.0020000.002000
H33B0.0400000.0170000.0290000.0070000.0020000.000000
C340.0138 (3)0.0112 (3)0.0107 (3)0.0011 (3)0.0006 (3)0.0008 (3)
H34A0.0230000.0290000.0260000.0000000.0050000.006000
C350.0145 (3)0.0108 (3)0.0134 (4)0.0022 (3)0.0005 (3)0.0015 (3)
H35A0.0340000.0170000.0340000.0020000.0020000.000000
C360.0206 (4)0.0118 (3)0.0164 (4)0.0035 (3)0.0010 (3)0.0007 (3)
H36A0.0520000.0280000.0290000.0040000.0100000.006000
H36B0.0350000.0280000.0500000.0130000.0090000.000000
H36C0.0470000.0240000.0370000.0040000.0080000.007000
C370.0223 (4)0.0175 (4)0.0137 (4)0.0013 (3)0.0037 (3)0.0005 (3)
H37A0.0340000.0380000.0380000.0130000.0140000.002000
H37B0.0420000.0190000.0370000.0020000.0090000.001000
H37C0.0430000.0420000.0230000.0090000.0040000.001000
C380.0147 (4)0.0182 (4)0.0180 (4)0.0041 (3)0.0011 (3)0.0028 (3)
H38A0.0270000.0440000.0520000.0160000.0050000.010000
H38B0.0390000.0370000.0490000.0140000.0090000.016000
H38C0.0330000.0500000.0240000.0000000.0020000.007000
C390.0191 (4)0.0204 (4)0.0143 (4)0.0031 (3)0.0026 (3)0.0041 (3)
H39A0.0360000.0600000.0350000.0210000.0080000.009000
H39B0.0400000.0480000.0320000.0060000.0040000.013000
H39C0.0510000.0340000.0290000.0030000.0050000.005000
Geometric parameters (Å, º) top
Ni1—H1A1.66 (2)C14—C191.4325 (12)
Ni1—H1B1.686 (19)C15—H15A1.106 (16)
Ni1—In12.4787 (1)C15—C161.3981 (13)
Ni1—P12.2833 (2)C16—H16A1.109 (16)
Ni1—P22.2528 (2)C16—C171.3927 (14)
Ni1—P32.2501 (2)C17—H17A1.111 (17)
H1A—H1B0.96 (3)C17—C181.3940 (13)
In1—N12.1114 (7)C18—H18A1.097 (16)
In1—N22.1229 (7)C18—C191.4122 (12)
In1—N32.1140 (7)C20—H20A1.117 (16)
In1—N42.3680 (7)C20—H20B1.110 (15)
P1—C71.8646 (9)C21—H21A1.098 (16)
P1—C81.8702 (9)C21—C231.5292 (14)
P1—C91.8649 (9)C21—C241.5345 (13)
P2—C201.8724 (9)C22—H22A1.096 (15)
P2—C211.8586 (9)C22—C251.5305 (15)
P2—C221.8783 (9)C22—C261.5333 (13)
P3—C331.8886 (9)C23—H23A1.099 (18)
P3—C341.8676 (9)C23—H23B1.12 (2)
P3—C351.8553 (9)C23—H23C1.07 (2)
N1—C61.3646 (12)C24—H24A1.180 (19)
N1—C71.4431 (12)C24—H24B1.086 (19)
N2—C191.3669 (11)C24—H24C1.069 (18)
N2—C201.4466 (11)C25—H25A1.112 (16)
N3—C321.3712 (10)C25—H25B1.09 (2)
N3—C331.4402 (11)C25—H25C1.088 (19)
N4—C11.4641 (10)C26—H26A1.100 (17)
N4—C141.4564 (11)C26—H26B1.103 (19)
N4—C271.4609 (10)C26—H26C1.071 (18)
C1—C21.3879 (12)C27—C281.3855 (11)
C1—C61.4303 (12)C27—C321.4277 (11)
C2—H2A1.044 (15)C28—H28A1.104 (16)
C2—C31.4010 (13)C28—C291.3990 (13)
C3—H3A1.081 (16)C29—H29A1.058 (16)
C3—C41.3951 (13)C29—C301.3885 (14)
C4—H4A1.087 (16)C30—H30A1.086 (16)
C4—C51.3927 (12)C30—C311.3928 (13)
C5—H5A1.099 (15)C31—H31A1.039 (15)
C5—C61.4138 (12)C31—C321.4102 (12)
C7—H7A1.102 (16)C33—H33A1.112 (15)
C7—H7B1.100 (16)C33—H33B1.084 (14)
C8—H8A1.119 (17)C34—H34A1.098 (15)
C8—C101.5354 (14)C34—C361.5329 (13)
C8—C111.5311 (15)C34—C371.5319 (13)
C9—H9A1.116 (16)C35—H35A1.095 (16)
C9—C121.5330 (14)C35—C381.5342 (14)
C9—C131.5261 (14)C35—C391.5328 (14)
C10—H10A1.10 (2)C36—H36A1.045 (16)
C10—H10B1.13 (2)C36—H36B1.13 (2)
C10—H10C1.11 (2)C36—H36C1.11 (2)
C11—H11A1.103 (18)C37—H37A1.088 (17)
C11—H11B1.11 (2)C37—H37B1.054 (18)
C11—H11C1.03 (2)C37—H37C1.062 (18)
C12—H12A1.077 (17)C38—H38A1.072 (18)
C12—H12B1.08 (2)C38—H38B1.11 (2)
C12—H12C1.11 (2)C38—H38C1.116 (19)
C13—H13A1.091 (18)C39—H39A1.075 (19)
C13—H13B1.07 (2)C39—H39B1.11 (2)
C13—H13C1.11 (2)C39—H39C1.08 (2)
C14—C151.3866 (11)
H1B—Ni1—H1A33.4 (9)C15—C14—N4121.39 (8)
In1—Ni1—H1A159.5 (8)C19—C14—N4117.97 (7)
In1—Ni1—H1B164.3 (8)C19—C14—C15120.62 (7)
P1—Ni1—H1A87.6 (8)H15A—C15—C14117.2 (9)
P1—Ni1—H1B95.1 (8)C16—C15—C14121.54 (8)
P1—Ni1—In181.139 (6)C16—C15—H15A121.1 (9)
P2—Ni1—H1A89.5 (8)H16A—C16—C15120.8 (10)
P2—Ni1—H1B112.1 (8)C17—C16—C15118.58 (8)
P2—Ni1—In182.400 (7)C17—C16—H16A120.6 (10)
P2—Ni1—P1122.762 (9)H17A—C17—C16120.3 (10)
P3—Ni1—H1A115.9 (8)C18—C17—C16120.85 (8)
P3—Ni1—H1B84.2 (7)C18—C17—H17A118.8 (10)
P3—Ni1—In184.562 (6)H18A—C18—C17120.3 (9)
P3—Ni1—P1120.206 (9)C19—C18—C17121.59 (8)
P3—Ni1—P2112.154 (9)C19—C18—H18A118.1 (9)
H1B—H1A—Ni175.1 (19)C14—C19—N2118.76 (7)
H1A—H1B—Ni171.6 (18)C18—C19—N2124.42 (8)
N1—In1—Ni1104.65 (2)C18—C19—C14116.82 (7)
N2—In1—Ni1102.74 (2)N2—C20—P2108.28 (6)
N2—In1—N1116.49 (3)H20A—C20—P2108.1 (8)
N3—In1—Ni1103.267 (19)H20A—C20—N2114.6 (9)
N3—In1—N1111.73 (3)H20B—C20—P2110.3 (8)
N3—In1—N2115.84 (3)H20B—C20—N2110.7 (9)
N4—In1—Ni1178.604 (17)H20B—C20—H20A104.8 (12)
N4—In1—N176.63 (3)H21A—C21—P2106.9 (8)
N4—In1—N276.10 (3)C23—C21—P2112.41 (6)
N4—In1—N376.67 (2)C23—C21—H21A107.5 (9)
C7—P1—Ni1117.46 (3)C24—C21—P2110.06 (6)
C8—P1—Ni1110.57 (3)C24—C21—H21A109.9 (8)
C8—P1—C7103.33 (4)C24—C21—C23110.00 (8)
C9—P1—Ni1116.58 (3)H22A—C22—P2104.8 (9)
C9—P1—C7102.05 (4)C25—C22—P2111.01 (6)
C9—P1—C8105.35 (4)C25—C22—H22A109.9 (9)
C20—P2—Ni1117.99 (3)C26—C22—P2115.85 (7)
C21—P2—Ni1114.42 (3)C26—C22—H22A106.1 (9)
C21—P2—C20102.57 (4)C26—C22—C25108.93 (8)
C22—P2—Ni1117.36 (3)H23A—C23—C21110.1 (11)
C22—P2—C20100.53 (4)H23B—C23—C21108.5 (10)
C22—P2—C21101.41 (4)H23B—C23—H23A108.4 (15)
C33—P3—Ni1118.83 (2)H23C—C23—C21113.7 (10)
C34—P3—Ni1112.79 (3)H23C—C23—H23A105.6 (15)
C34—P3—C3399.09 (4)H23C—C23—H23B110.4 (13)
C35—P3—Ni1118.86 (3)H24A—C24—C21113.1 (9)
C35—P3—C3399.58 (4)H24B—C24—C21111.2 (9)
C35—P3—C34104.90 (4)H24B—C24—H24A106.1 (14)
C6—N1—In1112.98 (6)H24C—C24—C21111.2 (10)
C7—N1—In1115.70 (6)H24C—C24—H24A109.2 (15)
C7—N1—C6119.50 (7)H24C—C24—H24B105.6 (12)
C19—N2—In1112.98 (5)H25A—C25—C22109.1 (9)
C20—N2—In1118.06 (5)H25B—C25—C22108.3 (9)
C20—N2—C19120.63 (7)H25B—C25—H25A110.1 (13)
C32—N3—In1113.12 (5)H25C—C25—C22114.8 (9)
C33—N3—In1118.72 (5)H25C—C25—H25A108.3 (13)
C33—N3—C32119.66 (7)H25C—C25—H25B106.2 (12)
C1—N4—In1103.12 (5)H26A—C26—C22109.2 (9)
C14—N4—In1103.44 (5)H26B—C26—C22114.2 (9)
C14—N4—C1115.80 (6)H26B—C26—H26A105.5 (14)
C27—N4—In1102.66 (5)H26C—C26—C22111.7 (9)
C27—N4—C1113.54 (6)H26C—C26—H26A110.0 (13)
C27—N4—C14115.76 (6)H26C—C26—H26B106.1 (13)
C2—C1—N4121.35 (7)C28—C27—N4121.13 (7)
C6—C1—N4117.99 (7)C32—C27—N4117.97 (7)
C6—C1—C2120.59 (8)C32—C27—C28120.90 (7)
H2A—C2—C1118.7 (9)H28A—C28—C27116.6 (8)
C3—C2—C1121.45 (8)C29—C28—C27121.22 (8)
C3—C2—H2A119.7 (9)C29—C28—H28A122.1 (8)
H3A—C3—C2122.5 (10)H29A—C29—C28119.5 (9)
C4—C3—C2118.62 (8)C30—C29—C28118.52 (8)
C4—C3—H3A118.8 (10)C30—C29—H29A122.0 (9)
H4A—C4—C3118.5 (9)H30A—C30—C29120.9 (9)
C5—C4—C3120.78 (8)C31—C30—C29121.11 (8)
C5—C4—H4A120.7 (9)C31—C30—H30A118.0 (9)
H5A—C5—C4119.0 (9)H31A—C31—C30115.6 (9)
C6—C5—C4121.57 (8)C32—C31—C30121.37 (8)
C6—C5—H5A119.4 (9)C32—C31—H31A123.0 (9)
C1—C6—N1119.15 (8)C27—C32—N3119.31 (7)
C5—C6—N1123.85 (8)C31—C32—N3123.90 (7)
C5—C6—C1116.99 (8)C31—C32—C27116.79 (7)
N1—C7—P1108.68 (6)N3—C33—P3111.65 (5)
H7A—C7—P1105.8 (9)H33A—C33—P3107.5 (9)
H7A—C7—N1115.7 (8)H33A—C33—N3111.1 (9)
H7B—C7—P1110.7 (8)H33B—C33—P3107.3 (9)
H7B—C7—N1111.2 (9)H33B—C33—N3111.8 (8)
H7B—C7—H7A104.6 (12)H33B—C33—H33A107.2 (12)
H8A—C8—P1103.7 (9)H34A—C34—P3102.8 (8)
C10—C8—P1117.20 (7)C36—C34—P3114.77 (6)
C10—C8—H8A105.9 (9)C36—C34—H34A108.9 (9)
C11—C8—P1110.55 (7)C37—C34—P3113.46 (6)
C11—C8—H8A107.4 (9)C37—C34—H34A105.4 (9)
C11—C8—C10111.19 (9)C37—C34—C36110.65 (7)
H9A—C9—P1104.2 (9)H35A—C35—P3105.1 (9)
C12—C9—P1109.98 (6)C38—C35—P3108.60 (6)
C12—C9—H9A108.2 (9)C38—C35—H35A110.1 (9)
C13—C9—P1116.70 (7)C39—C35—P3113.29 (6)
C13—C9—H9A108.6 (9)C39—C35—H35A108.1 (9)
C13—C9—C12108.83 (9)C39—C35—C38111.53 (8)
H10A—C10—C8112.5 (11)H36A—C36—C34112.6 (10)
H10B—C10—C8109.2 (10)H36B—C36—C34110.9 (9)
H10B—C10—H10A107.1 (16)H36B—C36—H36A107.9 (14)
H10C—C10—C8113.3 (10)H36C—C36—C34109.8 (9)
H10C—C10—H10A104.1 (16)H36C—C36—H36A109.2 (14)
H10C—C10—H10B110.3 (14)H36C—C36—H36B106.2 (13)
H11A—C11—C8106.9 (10)H37A—C37—C34110.4 (10)
H11B—C11—C8112.8 (10)H37B—C37—C34109.4 (9)
H11B—C11—H11A109.4 (15)H37B—C37—H37A108.8 (14)
H11C—C11—C8112.5 (10)H37C—C37—C34113.6 (9)
H11C—C11—H11A107.1 (16)H37C—C37—H37A105.9 (15)
H11C—C11—H11B108.0 (14)H37C—C37—H37B108.7 (13)
H12A—C12—C9108.3 (10)H38A—C38—C35110.3 (10)
H12B—C12—C9108.1 (10)H38B—C38—C35110.8 (10)
H12B—C12—H12A110.3 (14)H38B—C38—H38A106.1 (15)
H12C—C12—C9107.9 (10)H38C—C38—C35109.0 (9)
H12C—C12—H12A109.5 (15)H38C—C38—H38A110.7 (14)
H12C—C12—H12B112.5 (13)H38C—C38—H38B109.9 (13)
H13A—C13—C9111.2 (11)H39A—C39—C35113.5 (10)
H13B—C13—C9115.6 (11)H39B—C39—C35110.0 (9)
H13B—C13—H13A107.2 (15)H39B—C39—H39A110.9 (16)
H13C—C13—C9111.3 (10)H39C—C39—C35113.5 (10)
H13C—C13—H13A106.8 (15)H39C—C39—H39A102.1 (15)
H13C—C13—H13B104.2 (15)H39C—C39—H39B106.4 (13)
(GOJNIF_HAR_SHADE3_1) top
Crystal data top
C39H62InN4NiP3Dx = 1.415 Mg m3
Mr = 853.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9537 reflections
a = 12.2127 (4) Åθ = 2.3–36.4°
b = 14.5402 (5) ŵ = 1.20 mm1
c = 22.5601 (8) ÅT = 100 K
V = 4006.1 (2) Å3Block, gold
Z = 40.14 × 0.08 × 0.06 mm
F(000) = 105.781
Data collection top
Bruker Photon-II CMOS
diffractometer
18741 reflections with I 2u(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
SADABS. R.Blessing, 1995
θmax = 36.4°, θmin = 2.3°
Tmin = 0.701, Tmax = 0.747h = 2020
237431 measured reflectionsk = 2424
19473 independent reflectionsl = 3737
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullOnly H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.025 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091(Δ/σ)max = 0.001
S = 0.81Δρmax = 0.28 e Å3
19473 reflectionsΔρmin = 1.33 e Å3
619 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
0 restraintsAbsolute structure parameter: 0.231 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.755786 (14)0.598658 (12)0.856175 (8)0.00943 (3)
H1A0.732 (4)0.560 (3)0.9253 (17)0.032933
H1B0.740 (4)0.624 (3)0.9285 (16)0.032963
In10.798243 (7)0.580827 (5)0.749338 (4)0.00930 (2)
P10.91844 (3)0.52223 (2)0.864360 (15)0.00939 (5)
P20.59901 (3)0.52857 (2)0.829156 (15)0.00947 (5)
P30.75363 (3)0.75012 (2)0.835668 (15)0.00918 (5)
N10.96186 (9)0.53386 (8)0.74739 (6)0.01099 (16)
N20.67673 (10)0.48664 (9)0.72030 (5)0.01135 (18)
N30.78426 (10)0.71625 (8)0.71621 (5)0.01067 (17)
N40.83422 (9)0.56334 (8)0.64688 (5)0.00898 (16)
C10.95346 (10)0.57160 (9)0.64333 (6)0.00938 (18)
C21.00509 (12)0.59718 (10)0.59116 (6)0.0132 (2)
H2A0.956 (3)0.611 (2)0.5552 (12)0.026173
C31.11903 (12)0.60874 (11)0.58828 (6)0.0148 (2)
H3A1.172 (3)0.630 (2)0.5556 (13)0.029180
C41.18048 (12)0.59553 (10)0.63980 (7)0.0146 (2)
H4A1.262 (2)0.605 (2)0.6377 (13)0.029900
C51.12989 (11)0.57056 (10)0.69278 (6)0.0128 (2)
H5A1.180 (3)0.564 (2)0.7317 (13)0.026790
C61.01537 (11)0.55736 (9)0.69641 (6)0.0100 (2)
C71.01944 (12)0.53670 (10)0.80310 (6)0.0116 (2)
H7A1.059 (3)0.600 (2)0.8133 (13)0.025617
H7B1.085 (3)0.483 (2)0.8057 (13)0.026373
C80.99550 (13)0.56223 (11)0.93117 (6)0.0142 (2)
H8A0.983 (2)0.635 (2)0.9291 (13)0.023160
C90.91098 (12)0.39470 (10)0.87153 (7)0.0139 (2)
H9A0.851 (3)0.382 (2)0.9082 (13)0.024073
C101.12026 (15)0.55058 (15)0.93054 (9)0.0227 (3)
H10A1.149 (3)0.474 (2)0.9294 (16)0.032013
H10B1.164 (3)0.580 (2)0.8972 (13)0.029943
H10C1.149 (3)0.579 (3)0.9806 (16)0.033943
C110.94535 (18)0.52143 (16)0.98759 (8)0.0262 (4)
H11A0.998 (3)0.550 (3)1.0198 (13)0.032467
H11B0.860 (2)0.528 (2)0.9952 (14)0.028553
H11C0.960 (3)0.448 (2)0.9894 (14)0.033707
C120.86456 (15)0.35257 (11)0.81432 (8)0.0186 (3)
H12A0.852 (3)0.283 (2)0.8258 (14)0.030940
H12B0.779 (3)0.390 (2)0.8026 (14)0.028060
H12C0.925 (3)0.360 (2)0.7813 (13)0.029693
C131.01659 (16)0.34496 (13)0.88744 (10)0.0239 (3)
H13A1.004 (3)0.272 (2)0.8915 (15)0.033140
H13B1.087 (3)0.367 (3)0.8607 (14)0.032587
H13C1.054 (3)0.355 (2)0.9235 (13)0.032957
C140.78948 (11)0.47295 (9)0.63327 (6)0.00992 (18)
C150.82591 (12)0.42276 (10)0.58484 (6)0.0123 (2)
H15A0.896 (3)0.456 (2)0.5564 (13)0.025920
C160.78539 (13)0.33499 (10)0.57248 (7)0.0153 (2)
H16A0.810 (3)0.301 (2)0.5314 (14)0.029147
C170.70733 (13)0.29742 (10)0.61055 (7)0.0158 (2)
H17A0.668 (3)0.229 (2)0.5970 (15)0.030350
C180.67022 (13)0.34625 (10)0.65968 (7)0.0142 (2)
H18A0.615 (3)0.315 (2)0.6915 (13)0.027480
C190.70911 (11)0.43560 (9)0.67263 (6)0.01043 (19)
C200.60314 (11)0.44849 (10)0.76429 (6)0.0118 (2)
H20A0.628 (3)0.376 (2)0.7803 (14)0.026297
H20B0.520 (2)0.440 (2)0.7453 (13)0.027083
C210.53637 (12)0.45618 (10)0.88806 (6)0.0134 (2)
H21A0.463 (3)0.421 (2)0.8675 (13)0.026133
C220.48074 (11)0.60408 (10)0.80768 (6)0.0123 (2)
H22A0.480 (3)0.659 (2)0.8417 (13)0.023530
C230.61423 (15)0.38117 (13)0.91011 (7)0.0203 (3)
H23A0.574 (3)0.341 (2)0.9450 (14)0.033403
H23B0.635 (3)0.329 (2)0.8733 (14)0.030193
H23C0.684 (3)0.414 (2)0.9314 (15)0.030337
C240.49905 (15)0.51671 (12)0.94003 (7)0.0186 (3)
H24A0.440 (3)0.575 (3)0.9219 (15)0.030587
H24B0.458 (3)0.476 (2)0.9703 (13)0.033750
H24C0.565 (3)0.551 (2)0.9633 (14)0.029967
C250.49927 (13)0.64744 (12)0.74684 (8)0.0173 (2)
H25A0.439 (3)0.699 (2)0.7355 (14)0.031203
H25B0.574 (2)0.678 (2)0.7386 (13)0.027960
H25C0.497 (3)0.589 (2)0.7157 (14)0.030697
C260.36780 (12)0.55804 (12)0.80856 (8)0.0171 (3)
H26A0.301 (3)0.607 (2)0.8026 (15)0.034020
H26B0.365 (3)0.503 (2)0.7761 (14)0.033997
H26C0.337 (3)0.527 (3)0.8488 (13)0.033143
C270.77563 (11)0.64134 (9)0.62082 (6)0.01047 (19)
C280.74267 (14)0.63999 (10)0.56205 (6)0.0144 (2)
H28A0.750 (3)0.574 (2)0.5366 (13)0.026503
C290.69216 (15)0.71651 (11)0.53615 (7)0.0182 (3)
H29A0.663 (3)0.708 (2)0.4939 (12)0.030493
C300.67555 (14)0.79446 (11)0.57063 (7)0.0170 (3)
H30A0.637 (3)0.859 (3)0.5432 (15)0.031337
C310.70544 (12)0.79587 (10)0.63021 (6)0.0134 (2)
H31A0.692 (3)0.856 (2)0.6470 (12)0.027447
C320.75541 (11)0.71941 (9)0.65751 (6)0.01039 (19)
C330.74806 (12)0.78793 (8)0.75563 (6)0.01161 (19)
H33A0.658 (3)0.804 (2)0.7483 (14)0.025540
H33B0.801 (2)0.848 (2)0.7508 (12)0.026013
C340.62768 (12)0.80867 (10)0.86343 (6)0.0119 (2)
H34A0.562 (3)0.783 (2)0.8335 (13)0.023143
C350.86861 (12)0.82273 (10)0.86214 (7)0.0132 (2)
H35A0.845 (3)0.889 (2)0.8459 (13)0.024117
C360.63049 (13)0.91382 (10)0.85994 (7)0.0163 (2)
H36A0.658 (3)0.940 (2)0.8265 (12)0.031200
H36B0.547 (3)0.932 (2)0.8720 (16)0.031940
H36C0.683 (3)0.940 (2)0.8946 (14)0.031447
C370.59266 (15)0.77694 (11)0.92545 (7)0.0180 (3)
H37A0.516 (3)0.807 (3)0.9352 (14)0.029693
H37B0.589 (3)0.706 (2)0.9319 (13)0.027917
H37C0.645 (3)0.799 (2)0.9556 (12)0.029467
C380.97448 (13)0.78997 (12)0.83206 (7)0.0170 (2)
H38A1.032 (3)0.838 (2)0.8393 (14)0.030140
H38B0.993 (3)0.727 (2)0.8529 (14)0.028413
H38C0.963 (3)0.777 (2)0.7811 (14)0.028310
C390.87987 (14)0.82434 (12)0.92961 (7)0.0181 (3)
H39A0.943 (3)0.870 (3)0.9479 (14)0.031073
H39B0.814 (3)0.858 (2)0.9492 (13)0.031150
H39C0.876 (3)0.755 (2)0.9479 (14)0.029307
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.00868 (6)0.00821 (6)0.01140 (7)0.00034 (5)0.00037 (5)0.00001 (5)
H1A0.0438400.0320000.0229600.0069100.0034700.004980
H1B0.0468200.0298000.0222700.0027100.0005200.005120
In10.00952 (4)0.00876 (4)0.00961 (4)0.00009 (2)0.00013 (3)0.00013 (3)
P10.01007 (12)0.00966 (12)0.00844 (12)0.00076 (10)0.00067 (10)0.00063 (10)
P20.00875 (12)0.01086 (13)0.00881 (12)0.00171 (10)0.00051 (10)0.00018 (10)
P30.01108 (13)0.00768 (11)0.00876 (12)0.00026 (11)0.00057 (10)0.00083 (9)
N10.0093 (4)0.0137 (4)0.0100 (4)0.0009 (3)0.0001 (4)0.0015 (4)
N20.0119 (4)0.0122 (4)0.0099 (4)0.0018 (4)0.0014 (3)0.0024 (3)
N30.0146 (5)0.0088 (4)0.0086 (4)0.0017 (4)0.0010 (3)0.0004 (3)
N40.0107 (4)0.0090 (4)0.0073 (4)0.0011 (3)0.0013 (3)0.0001 (3)
C10.0096 (4)0.0096 (4)0.0090 (4)0.0005 (4)0.0020 (4)0.0002 (4)
C20.0144 (5)0.0136 (5)0.0115 (5)0.0001 (4)0.0031 (4)0.0002 (4)
H2A0.0267400.0322900.0194900.0012300.0011400.002660
C30.0146 (5)0.0165 (6)0.0133 (5)0.0013 (5)0.0041 (4)0.0011 (4)
H3A0.0285300.0367100.0223000.0025900.0087200.002720
C40.0114 (5)0.0154 (5)0.0169 (5)0.0009 (4)0.0038 (4)0.0009 (5)
H4A0.0178400.0406400.0312200.0032700.0044400.000140
C50.0101 (5)0.0155 (5)0.0128 (5)0.0002 (4)0.0008 (4)0.0007 (4)
H5A0.0208800.0363100.0231800.0002200.0023800.001550
C60.0096 (5)0.0108 (5)0.0096 (5)0.0006 (4)0.0014 (4)0.0004 (4)
C70.0107 (5)0.0143 (5)0.0099 (5)0.0005 (4)0.0004 (4)0.0004 (4)
H7A0.0249200.0254100.0265200.0073500.0015900.001430
H7B0.0231300.0282000.0277900.0092600.0008100.001380
C80.0154 (5)0.0160 (6)0.0112 (5)0.0014 (4)0.0020 (4)0.0006 (4)
H8A0.0238800.0209800.0246200.0007900.0016600.000460
C90.0154 (5)0.0108 (5)0.0154 (5)0.0016 (4)0.0001 (4)0.0028 (4)
H9A0.0258200.0250000.0214000.0006700.0036900.003120
C100.0161 (6)0.0298 (8)0.0222 (7)0.0002 (6)0.0083 (5)0.0036 (6)
H10A0.0289900.0267100.0403400.0069800.0013600.001020
H10B0.0243400.0364500.0290400.0004800.0019800.008010
H10C0.0266500.0497100.0254700.0011100.0081100.007630
C110.0330 (9)0.0343 (9)0.0112 (6)0.0104 (8)0.0003 (6)0.0006 (6)
H11A0.0332600.0441000.0200400.0058700.0067500.000640
H11B0.0207700.0360000.0288900.0028800.0008900.005010
H11C0.0457600.0226300.0327300.0062100.0048000.004840
C120.0250 (7)0.0121 (5)0.0187 (6)0.0007 (5)0.0016 (5)0.0024 (5)
H12A0.0460900.0159500.0307800.0030600.0025800.002690
H12B0.0242700.0297800.0301300.0081700.0053900.002730
H12C0.0266000.0389000.0235800.0042300.0071800.001680
C130.0195 (7)0.0150 (6)0.0373 (10)0.0049 (5)0.0050 (7)0.0054 (6)
H13A0.0371900.0202600.0419700.0052700.0039800.003940
H13B0.0264600.0404800.0308200.0066800.0059900.009580
H13C0.0357200.0401500.0230000.0089800.0077400.002200
C140.0123 (5)0.0086 (4)0.0089 (4)0.0016 (4)0.0001 (4)0.0012 (4)
C150.0154 (5)0.0119 (5)0.0097 (5)0.0002 (4)0.0007 (4)0.0018 (4)
H15A0.0280300.0258700.0238600.0030200.0069900.001480
C160.0195 (6)0.0131 (5)0.0133 (5)0.0009 (5)0.0012 (4)0.0055 (4)
H16A0.0363000.0268700.0242700.0007200.0057000.009510
C170.0178 (6)0.0124 (5)0.0172 (6)0.0031 (5)0.0003 (5)0.0049 (4)
H17A0.0375600.0214500.0320400.0083200.0032300.008260
C180.0146 (5)0.0121 (5)0.0160 (5)0.0029 (4)0.0008 (4)0.0040 (4)
H18A0.0294900.0256300.0273200.0079400.0068200.002860
C190.0107 (5)0.0109 (5)0.0097 (4)0.0005 (4)0.0003 (4)0.0022 (4)
C200.0107 (5)0.0131 (5)0.0117 (5)0.0032 (4)0.0017 (4)0.0016 (4)
H20A0.0317800.0188100.0283000.0002500.0029500.002210
H20B0.0188400.0344500.0279600.0054700.0023000.004060
C210.0129 (5)0.0161 (6)0.0113 (5)0.0036 (4)0.0007 (4)0.0011 (4)
H21A0.0218800.0283100.0282100.0074200.0001600.003290
C220.0095 (4)0.0155 (5)0.0120 (5)0.0005 (4)0.0010 (4)0.0021 (4)
H22A0.0232900.0252500.0220500.0002100.0009800.005670
C230.0213 (7)0.0220 (7)0.0175 (6)0.0002 (6)0.0027 (5)0.0070 (5)
H23A0.0346200.0302500.0353400.0050400.0107300.011730
H23B0.0367700.0283700.0254400.0036600.0037600.005620
H23C0.0287300.0255300.0367500.0046600.0084900.002600
C240.0244 (7)0.0213 (7)0.0102 (5)0.0060 (6)0.0030 (5)0.0013 (5)
H24A0.0285200.0316800.0315600.0068400.0015600.002660
H24B0.0410600.0316600.0285300.0086300.0141700.001890
H24C0.0220400.0369500.0309100.0057400.0011500.009110
C250.0167 (5)0.0196 (6)0.0156 (6)0.0027 (4)0.0016 (5)0.0025 (5)
H25A0.0266900.0366600.0302600.0139700.0002500.003440
H25B0.0200000.0361300.0277500.0066800.0006900.002270
H25C0.0418600.0274100.0228200.0028000.0003100.008220
C260.0104 (5)0.0222 (7)0.0187 (6)0.0020 (5)0.0011 (4)0.0028 (5)
H26A0.0196800.0371900.0451900.0036700.0029700.000680
H26B0.0278400.0377400.0364100.0067100.0042900.017020
H26C0.0279800.0464200.0250300.0089300.0042900.002010
C270.0143 (5)0.0092 (4)0.0079 (4)0.0017 (4)0.0007 (4)0.0000 (4)
C280.0210 (6)0.0128 (5)0.0095 (5)0.0039 (5)0.0024 (4)0.0012 (4)
H28A0.0347400.0234400.0213300.0057800.0010500.005150
C290.0270 (7)0.0173 (6)0.0104 (5)0.0080 (5)0.0059 (5)0.0007 (4)
H29A0.0414400.0335600.0164800.0083300.0049100.000270
C300.0244 (7)0.0151 (6)0.0114 (5)0.0081 (5)0.0036 (5)0.0008 (4)
H30A0.0435800.0258800.0245500.0132900.0033900.004630
C310.0180 (6)0.0112 (5)0.0109 (5)0.0047 (4)0.0008 (4)0.0007 (4)
H31A0.0387700.0204900.0230800.0079200.0005300.002830
C320.0122 (5)0.0094 (4)0.0096 (4)0.0015 (4)0.0007 (4)0.0005 (3)
C330.0160 (5)0.0084 (4)0.0104 (5)0.0011 (4)0.0003 (4)0.0006 (4)
H33A0.0237100.0278800.0250300.0082800.0014900.000790
H33B0.0333700.0181000.0265700.0051100.0035200.000060
C340.0141 (5)0.0111 (5)0.0104 (5)0.0008 (4)0.0004 (4)0.0006 (4)
H34A0.0231600.0247300.0215400.0010300.0027000.002790
C350.0149 (5)0.0109 (5)0.0139 (5)0.0019 (4)0.0005 (4)0.0018 (4)
H35A0.0307000.0167100.0249400.0000100.0014600.000540
C360.0199 (6)0.0121 (5)0.0167 (6)0.0031 (5)0.0016 (5)0.0005 (4)
H36A0.0461200.0251100.0223700.0012500.0077000.002240
H36B0.0284900.0261500.0411800.0086200.0048600.002530
H36C0.0396000.0251300.0296100.0016900.0096700.004310
C370.0238 (7)0.0167 (6)0.0134 (5)0.0009 (5)0.0042 (5)0.0008 (5)
H37A0.0245200.0360800.0284800.0098700.0059200.000070
H37B0.0377400.0186500.0273600.0020000.0039100.000780
H37C0.0291900.0371000.0221100.0071900.0049800.002480
C380.0153 (6)0.0185 (6)0.0172 (6)0.0046 (5)0.0014 (5)0.0035 (5)
H38A0.0257100.0247900.0399200.0106400.0042100.007270
H38B0.0312100.0225300.0315000.0038400.0044600.007100
H38C0.0301900.0365800.0181600.0012900.0001600.004690
C390.0192 (6)0.0202 (6)0.0149 (6)0.0031 (5)0.0030 (5)0.0043 (5)
H39A0.0286600.0368000.0277600.0131400.0028700.004160
H39B0.0321800.0354000.0258700.0092200.0045900.005160
H39C0.0434600.0189500.0255100.0023800.0011400.002110
Geometric parameters (Å, º) top
Ni1—H1A1.68 (4)C14—C191.4306 (19)
Ni1—H1B1.68 (4)C15—H15A1.18 (3)
Ni1—In12.4790 (2)C15—C161.397 (2)
Ni1—P12.2836 (4)C16—H16A1.09 (3)
Ni1—P22.2530 (4)C16—C171.395 (2)
Ni1—P32.2505 (4)C17—H17A1.15 (3)
H1A—H1B0.94 (5)C17—C181.392 (2)
In1—N12.1121 (11)C18—H18A1.09 (3)
In1—N22.1230 (12)C18—C191.414 (2)
In1—N32.1131 (12)C20—H20A1.15 (3)
In1—N42.3667 (11)C20—H20B1.11 (3)
P1—C71.8643 (14)C21—H21A1.13 (3)
P1—C81.8697 (15)C21—C231.530 (2)
P1—C91.8636 (15)C21—C241.535 (2)
P2—C201.8707 (14)C22—H22A1.11 (3)
P2—C211.8599 (14)C22—C251.527 (2)
P2—C221.8780 (14)C22—C261.533 (2)
P3—C331.8888 (14)C23—H23A1.10 (3)
P3—C341.8664 (14)C23—H23B1.15 (3)
P3—C351.8555 (15)C23—H23C1.09 (3)
N1—C61.3662 (18)C24—H24A1.19 (4)
N1—C71.4408 (19)C24—H24B1.03 (3)
N2—C191.3652 (17)C24—H24C1.09 (3)
N2—C201.4492 (18)C25—H25A1.09 (3)
N3—C321.3713 (17)C25—H25B1.03 (3)
N3—C331.4395 (17)C25—H25C1.10 (3)
N4—C11.4633 (17)C26—H26A1.09 (3)
N4—C141.4561 (17)C26—H26B1.08 (3)
N4—C271.4642 (17)C26—H26C1.08 (3)
C1—C21.3860 (19)C27—C281.3858 (19)
C1—C61.4314 (19)C27—C321.4264 (19)
C2—H2A1.03 (3)C28—H28A1.12 (3)
C2—C31.403 (2)C28—C291.400 (2)
C3—H3A1.03 (3)C29—H29A1.03 (3)
C3—C41.397 (2)C29—C301.390 (2)
C4—H4A1.00 (3)C30—H30A1.22 (3)
C4—C51.394 (2)C30—C311.393 (2)
C5—H5A1.07 (3)C31—H31A0.97 (3)
C5—C61.414 (2)C31—C321.4098 (19)
C7—H7A1.06 (3)C33—H33A1.13 (3)
C7—H7B1.12 (3)C33—H33B1.09 (3)
C8—H8A1.07 (3)C34—H34A1.12 (3)
C8—C101.533 (2)C34—C361.531 (2)
C8—C111.532 (2)C34—C371.534 (2)
C9—H9A1.12 (3)C35—H35A1.08 (3)
C9—C121.537 (2)C35—C381.536 (2)
C9—C131.522 (2)C35—C391.528 (2)
C10—H10A1.16 (3)C36—H36A0.92 (3)
C10—H10B1.01 (3)C36—H36B1.09 (3)
C10—H10C1.26 (3)C36—H36C1.08 (3)
C11—H11A1.06 (3)C37—H37A1.06 (3)
C11—H11B1.06 (3)C37—H37B1.04 (3)
C11—H11C1.08 (3)C37—H37C0.99 (3)
C12—H12A1.05 (3)C38—H38A1.01 (3)
C12—H12B1.20 (3)C38—H38B1.06 (3)
C12—H12C1.05 (3)C38—H38C1.17 (3)
C13—H13A1.07 (3)C39—H39A1.09 (3)
C13—H13B1.10 (3)C39—H39B1.04 (3)
C13—H13C0.94 (3)C39—H39C1.10 (3)
C14—C151.3872 (18)
H1B—Ni1—H1A32.5 (17)C15—C14—N4121.37 (12)
In1—Ni1—H1A154.5 (14)C19—C14—N4117.98 (11)
In1—Ni1—H1B171.3 (15)C19—C14—C15120.62 (12)
P1—Ni1—H1A85.1 (16)H15A—C15—C14116.4 (16)
P1—Ni1—H1B97.5 (16)C16—C15—C14121.61 (13)
P1—Ni1—In181.129 (10)C16—C15—H15A121.9 (16)
P2—Ni1—H1A87.3 (15)H16A—C16—C15119.2 (17)
P2—Ni1—H1B105.4 (16)C17—C16—C15118.50 (13)
P2—Ni1—In182.380 (10)C17—C16—H16A122.0 (17)
P2—Ni1—P1122.749 (15)H17A—C17—C16117.5 (17)
P3—Ni1—H1A120.9 (14)C18—C17—C16120.87 (13)
P3—Ni1—H1B88.8 (14)C18—C17—H17A121.2 (17)
P3—Ni1—In184.544 (10)H18A—C18—C17120.8 (17)
P3—Ni1—P1120.198 (15)C19—C18—C17121.59 (14)
P3—Ni1—P2112.155 (15)C19—C18—H18A117.4 (17)
H1B—H1A—Ni174 (4)C14—C19—N2118.78 (12)
H1A—H1B—Ni174 (4)C18—C19—N2124.40 (13)
N1—In1—Ni1104.59 (3)C18—C19—C14116.81 (12)
N2—In1—Ni1102.78 (3)N2—C20—P2108.31 (9)
N2—In1—N1116.51 (5)H20A—C20—P2109.3 (16)
N3—In1—Ni1103.27 (3)H20A—C20—N2113.7 (16)
N3—In1—N1111.74 (5)H20B—C20—P2110.4 (16)
N3—In1—N2115.82 (5)H20B—C20—N2110.3 (16)
N4—In1—Ni1178.62 (3)H20B—C20—H20A105 (3)
N4—In1—N176.66 (4)H21A—C21—P2106.7 (16)
N4—In1—N276.06 (4)C23—C21—P2112.33 (10)
N4—In1—N376.69 (4)C23—C21—H21A107.7 (17)
C7—P1—Ni1117.43 (5)C24—C21—P2110.09 (11)
C8—P1—Ni1110.59 (5)C24—C21—H21A109.8 (16)
C8—P1—C7103.27 (7)C24—C21—C23110.18 (13)
C9—P1—Ni1116.66 (5)H22A—C22—P2104.5 (16)
C9—P1—C7102.06 (7)C25—C22—P2111.05 (10)
C9—P1—C8105.32 (7)C25—C22—H22A108.9 (16)
C20—P2—Ni1118.05 (5)C26—C22—P2115.67 (11)
C21—P2—Ni1114.34 (5)C26—C22—H22A107.4 (17)
C21—P2—C20102.58 (6)C26—C22—C25108.97 (12)
C22—P2—Ni1117.32 (5)H23A—C23—C21109.5 (19)
C22—P2—C20100.54 (6)H23B—C23—C21111.9 (17)
C22—P2—C21101.47 (7)H23B—C23—H23A105 (2)
C33—P3—Ni1118.80 (4)H23C—C23—C21108.3 (18)
C34—P3—Ni1112.77 (5)H23C—C23—H23A106 (3)
C34—P3—C3399.11 (6)H23C—C23—H23B116 (3)
C35—P3—Ni1118.80 (5)H24A—C24—C21109.2 (17)
C35—P3—C3399.75 (6)H24B—C24—C21108.6 (18)
C35—P3—C34104.84 (6)H24B—C24—H24A110 (3)
C6—N1—In1112.91 (9)H24C—C24—C21114.5 (17)
C7—N1—In1115.74 (9)H24C—C24—H24A106 (3)
C7—N1—C6119.58 (11)H24C—C24—H24B108 (3)
C19—N2—In1113.03 (9)H25A—C25—C22113.4 (17)
C20—N2—In1117.97 (8)H25B—C25—C22118.0 (17)
C20—N2—C19120.74 (12)H25B—C25—H25A105 (3)
C32—N3—In1113.18 (9)H25C—C25—C22104.7 (17)
C33—N3—In1118.75 (8)H25C—C25—H25A111 (3)
C33—N3—C32119.57 (11)H25C—C25—H25B104 (2)
C1—N4—In1103.26 (8)H26A—C26—C22112.8 (18)
C14—N4—In1103.49 (8)H26B—C26—C22109.8 (18)
C14—N4—C1115.85 (10)H26B—C26—H26A112 (3)
C27—N4—In1102.60 (7)H26C—C26—C22120.5 (18)
C27—N4—C1113.63 (11)H26C—C26—H26A96 (3)
C27—N4—C14115.54 (10)H26C—C26—H26B105 (3)
C2—C1—N4121.42 (12)C28—C27—N4121.00 (12)
C6—C1—N4117.91 (11)C32—C27—N4117.92 (11)
C6—C1—C2120.59 (12)C32—C27—C28121.07 (12)
H2A—C2—C1117.0 (17)H28A—C28—C27118.5 (16)
C3—C2—C1121.51 (14)C29—C28—C27121.07 (13)
C3—C2—H2A121.4 (17)C29—C28—H28A120.2 (16)
H3A—C3—C2133.7 (19)H29A—C29—C28116.3 (17)
C4—C3—C2118.55 (13)C30—C29—C28118.62 (13)
C4—C3—H3A107.6 (18)C30—C29—H29A124.7 (17)
H4A—C4—C3118.3 (17)H30A—C30—C29113.5 (17)
C5—C4—C3120.75 (13)C31—C30—C29120.93 (13)
C5—C4—H4A121.0 (17)C31—C30—H30A125.6 (17)
H5A—C5—C4118.2 (17)H31A—C31—C30110.2 (17)
C6—C5—C4121.57 (13)C32—C31—C30121.55 (13)
C6—C5—H5A120.1 (17)C32—C31—H31A128.0 (17)
C1—C6—N1119.19 (12)C27—C32—N3119.29 (11)
C5—C6—N1123.77 (13)C31—C32—N3124.02 (12)
C5—C6—C1117.02 (12)C31—C32—C27116.69 (11)
N1—C7—P1108.70 (9)N3—C33—P3111.64 (9)
H7A—C7—P1103.5 (17)H33A—C33—P3103.5 (16)
H7A—C7—N1115.7 (16)H33A—C33—N3110.7 (16)
H7B—C7—P1110.8 (15)H33B—C33—P3107.9 (15)
H7B—C7—N1112.0 (16)H33B—C33—N3109.7 (15)
H7B—C7—H7A106 (2)H33B—C33—H33A113 (2)
H8A—C8—P1101.6 (15)H34A—C34—P3103.6 (16)
C10—C8—P1117.28 (12)C36—C34—P3114.82 (10)
C10—C8—H8A104.5 (16)C36—C34—H34A108.9 (16)
C11—C8—P1110.37 (11)C37—C34—P3113.49 (10)
C11—C8—H8A111.2 (16)C37—C34—H34A104.5 (16)
C11—C8—C10111.24 (15)C37—C34—C36110.70 (12)
H9A—C9—P1104.7 (17)H35A—C35—P3101.5 (17)
C12—C9—P1109.98 (10)C38—C35—P3108.56 (10)
C12—C9—H9A108.4 (16)C38—C35—H35A110.8 (16)
C13—C9—P1116.87 (12)C39—C35—P3113.41 (11)
C13—C9—H9A107.8 (16)C39—C35—H35A110.5 (16)
C13—C9—C12108.74 (14)C39—C35—C38111.66 (13)
H10A—C10—C8113.7 (18)H36A—C36—C34118.3 (19)
H10B—C10—C8118.8 (18)H36B—C36—C34102.2 (19)
H10B—C10—H10A103 (3)H36B—C36—H36A117 (3)
H10C—C10—C8103.6 (17)H36C—C36—C34109.4 (18)
H10C—C10—H10A105 (3)H36C—C36—H36A103 (3)
H10C—C10—H10B112 (3)H36C—C36—H36B107 (3)
H11A—C11—C8100.1 (18)H37A—C37—C34108.2 (18)
H11B—C11—C8119.7 (17)H37B—C37—C34115.9 (16)
H11B—C11—H11A117 (3)H37B—C37—H37A110 (3)
H11C—C11—C8110.3 (17)H37C—C37—C34110.4 (18)
H11C—C11—H11A105 (3)H37C—C37—H37A107 (3)
H11C—C11—H11B104 (3)H37C—C37—H37B105 (3)
H12A—C12—C9103.3 (17)H38A—C38—C35107.2 (18)
H12B—C12—C9108.9 (16)H38B—C38—C35104.5 (17)
H12B—C12—H12A111 (3)H38B—C38—H38A113 (3)
H12C—C12—C9107.3 (18)H38C—C38—C35112.4 (17)
H12C—C12—H12A112 (3)H38C—C38—H38A111 (3)
H12C—C12—H12B114 (2)H38C—C38—H38B109 (2)
H13A—C13—C9111.8 (19)H39A—C39—C35116.7 (17)
H13B—C13—C9113.2 (17)H39B—C39—C35111.2 (17)
H13B—C13—H13A117 (3)H39B—C39—H39A96 (3)
H13C—C13—C9122 (2)H39C—C39—C35110.9 (17)
H13C—C13—H13A99 (3)H39C—C39—H39A117 (3)
H13C—C13—H13B93 (3)H39C—C39—H39B104 (3)
In1—N1—C6—C126.60 (10)N2—C19—C18—C17179.40 (14)
In1—N1—C6—C5152.09 (9)N3—C32—C27—N44.49 (15)
In1—N1—C7—P129.30 (7)N3—C32—C27—C28176.68 (13)
In1—N2—C19—C1426.60 (11)N3—C32—C31—C30178.48 (15)
In1—N2—C19—C18151.99 (10)N4—C1—C2—C3177.39 (13)
In1—N2—C20—P223.07 (8)N4—C1—C6—C5176.65 (12)
In1—N3—C32—C2722.08 (11)N4—C14—C15—C16178.26 (13)
In1—N3—C32—C31157.54 (10)N4—C14—C19—C18177.58 (12)
In1—N3—C33—P314.31 (9)N4—C27—C28—C29176.35 (15)
In1—N4—C1—C2157.14 (8)N4—C27—C32—C31175.86 (12)
In1—N4—C1—C619.47 (9)C1—C2—C3—C41.17 (17)
In1—N4—C14—C15156.94 (8)C1—C6—C5—C40.55 (15)
In1—N4—C14—C1920.89 (9)C2—C3—C4—C50.61 (17)
In1—N4—C27—C28156.96 (9)C3—C4—C5—C60.25 (17)
In1—N4—C27—C3224.22 (9)C14—C15—C16—C170.72 (17)
P1—C7—N1—C6169.71 (9)C14—C19—C18—C170.79 (15)
P2—C20—N2—C19169.29 (9)C15—C16—C17—C180.20 (18)
P3—C33—N3—C32160.14 (9)C16—C17—C18—C190.56 (19)
N1—C6—C1—N42.13 (15)C27—C28—C29—C300.03 (19)
N1—C6—C1—C2178.78 (13)C27—C32—C31—C301.14 (16)
N1—C6—C5—C4179.27 (14)C28—C29—C30—C311.9 (2)
N2—C19—C14—N41.12 (14)C29—C30—C31—C321.3 (2)
N2—C19—C14—C15178.97 (12)
(GOJNIF_HAR_SHADE3) top
Crystal data top
C39H62InN4NiP3Dx = 1.415 Mg m3
Mr = 853.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9537 reflections
a = 12.2127 (4) Åθ = 2.3–36.4°
b = 14.5402 (5) ŵ = 1.20 mm1
c = 22.5601 (8) ÅT = 100 K
V = 4006.1 (2) Å3Block, gold
Z = 40.14 × 0.08 × 0.06 mm
F(000) = 1787.122
Data collection top
Bruker Photon-II CMOS
diffractometer
18741 reflections with I 2u(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
SADABS. R.Blessing, 1995
θmax = 36.4°, θmin = 2.3°
Tmin = 0.701, Tmax = 0.747h = 2020
237431 measured reflectionsk = 2424
19473 independent reflectionsl = 3737
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullOnly H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.025 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091(Δ/σ)max = 0.001
S = 0.81Δρmax = 0.28 e Å3
19473 reflectionsΔρmin = 1.33 e Å3
619 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
0 restraintsAbsolute structure parameter: 0.231 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.755786 (14)0.598658 (12)0.856175 (8)0.00943 (3)
H1A0.732 (4)0.560 (3)0.9253 (17)0.032777
H1B0.740 (4)0.624 (3)0.9284 (16)0.032880
In10.798243 (7)0.580827 (5)0.749338 (4)0.00930 (2)
P10.91844 (3)0.52223 (2)0.864360 (15)0.00939 (5)
P20.59901 (3)0.52856 (2)0.829156 (15)0.00947 (5)
P30.75363 (3)0.75012 (2)0.835668 (15)0.00918 (5)
N10.96186 (9)0.53386 (8)0.74739 (6)0.01099 (16)
N20.67672 (10)0.48664 (9)0.72030 (5)0.01135 (18)
N30.78425 (10)0.71625 (8)0.71621 (5)0.01067 (17)
N40.83422 (9)0.56334 (8)0.64688 (5)0.00897 (16)
C10.95346 (10)0.57160 (9)0.64333 (6)0.00939 (18)
C21.00509 (12)0.59718 (10)0.59116 (6)0.0132 (2)
H2A0.955 (3)0.611 (2)0.5552 (12)0.026547
C31.11903 (12)0.60874 (11)0.58829 (6)0.0148 (2)
H3A1.172 (3)0.630 (2)0.5556 (13)0.029823
C41.18047 (12)0.59553 (10)0.63980 (7)0.0146 (2)
H4A1.262 (2)0.605 (2)0.6376 (14)0.030597
C51.12989 (11)0.57056 (10)0.69277 (6)0.0128 (2)
H5A1.180 (3)0.565 (2)0.7316 (13)0.027547
C61.01536 (11)0.55736 (9)0.69641 (6)0.0100 (2)
C71.01943 (12)0.53670 (10)0.80310 (6)0.0116 (2)
H7A1.058 (3)0.600 (2)0.8134 (13)0.026160
H7B1.085 (3)0.483 (2)0.8057 (13)0.027077
C80.99550 (13)0.56223 (11)0.93117 (6)0.0142 (2)
H8A0.983 (2)0.635 (2)0.9291 (13)0.023010
C90.91098 (12)0.39470 (10)0.87153 (7)0.0139 (2)
H9A0.851 (3)0.382 (2)0.9080 (13)0.023980
C101.12026 (15)0.55058 (15)0.93054 (9)0.0227 (3)
H10A1.149 (3)0.474 (2)0.9294 (16)0.032437
H10B1.164 (3)0.580 (2)0.8972 (13)0.030493
H10C1.149 (3)0.579 (3)0.9806 (16)0.034073
C110.94534 (18)0.52143 (16)0.98760 (8)0.0262 (4)
H11A0.999 (3)0.550 (3)1.0198 (14)0.031947
H11B0.860 (2)0.528 (2)0.9952 (14)0.028190
H11C0.960 (3)0.448 (2)0.9894 (14)0.033387
C120.86456 (15)0.35257 (11)0.81432 (8)0.0186 (3)
H12A0.852 (3)0.283 (2)0.8258 (14)0.031280
H12B0.779 (3)0.390 (2)0.8026 (14)0.028247
H12C0.925 (3)0.360 (2)0.7813 (13)0.030097
C131.01659 (16)0.34496 (13)0.88744 (10)0.0239 (3)
H13A1.005 (3)0.272 (2)0.8916 (15)0.033360
H13B1.087 (3)0.367 (3)0.8608 (14)0.032930
H13C1.054 (3)0.355 (2)0.9237 (13)0.033173
C140.78948 (11)0.47295 (9)0.63327 (6)0.00992 (18)
C150.82591 (12)0.42276 (10)0.58484 (6)0.0123 (2)
H15A0.896 (3)0.456 (2)0.5564 (13)0.026317
C160.78539 (13)0.33498 (10)0.57248 (7)0.0153 (2)
H16A0.810 (3)0.301 (2)0.5312 (14)0.029527
C170.70733 (13)0.29742 (10)0.61055 (7)0.0158 (2)
H17A0.668 (3)0.229 (2)0.5969 (15)0.031103
C180.67022 (13)0.34625 (10)0.65968 (7)0.0142 (2)
H18A0.615 (3)0.315 (2)0.6915 (13)0.027867
C190.70911 (11)0.43560 (9)0.67263 (6)0.01044 (19)
C200.60314 (11)0.44849 (10)0.76429 (6)0.0118 (2)
H20A0.628 (3)0.376 (2)0.7803 (14)0.026797
H20B0.520 (2)0.440 (2)0.7452 (13)0.027590
C210.53637 (12)0.45618 (10)0.88807 (6)0.0134 (2)
H21A0.464 (3)0.421 (2)0.8675 (13)0.026070
C220.48074 (11)0.60409 (10)0.80768 (6)0.0123 (2)
H22A0.480 (3)0.659 (2)0.8417 (13)0.023520
C230.61422 (15)0.38117 (13)0.91011 (7)0.0203 (3)
H23A0.574 (3)0.340 (2)0.9450 (14)0.032970
H23B0.635 (3)0.329 (2)0.8733 (14)0.030373
H23C0.684 (3)0.414 (2)0.9314 (15)0.029870
C240.49905 (15)0.51670 (12)0.94003 (7)0.0186 (3)
H24A0.440 (3)0.575 (3)0.9220 (15)0.030083
H24B0.458 (3)0.476 (2)0.9703 (13)0.033003
H24C0.565 (3)0.551 (2)0.9633 (14)0.029380
C250.49926 (13)0.64744 (12)0.74684 (8)0.0173 (2)
H25A0.439 (3)0.699 (2)0.7355 (14)0.031697
H25B0.574 (2)0.677 (2)0.7386 (13)0.028417
H25C0.497 (3)0.589 (2)0.7157 (14)0.031093
C260.36780 (12)0.55803 (12)0.80856 (8)0.0171 (3)
H26A0.301 (3)0.607 (2)0.8027 (15)0.034310
H26B0.365 (3)0.504 (2)0.7763 (14)0.034193
H26C0.337 (3)0.527 (3)0.8488 (13)0.033460
C270.77563 (11)0.64134 (9)0.62082 (6)0.01046 (19)
C280.74267 (14)0.63999 (10)0.56205 (6)0.0144 (2)
H28A0.750 (3)0.574 (2)0.5367 (13)0.026897
C290.69216 (15)0.71651 (11)0.53615 (7)0.0182 (3)
H29A0.663 (3)0.708 (2)0.4939 (12)0.030690
C300.67556 (14)0.79446 (11)0.57063 (7)0.0170 (3)
H30A0.637 (3)0.859 (3)0.5432 (15)0.032427
C310.70544 (12)0.79587 (10)0.63021 (6)0.0134 (2)
H31A0.693 (3)0.857 (2)0.6468 (12)0.028243
C320.75541 (11)0.71941 (9)0.65751 (6)0.01039 (19)
C330.74806 (12)0.78793 (8)0.75563 (6)0.01161 (19)
H33A0.659 (3)0.804 (2)0.7483 (14)0.026027
H33B0.801 (2)0.848 (2)0.7508 (12)0.026610
C340.62768 (12)0.80867 (10)0.86343 (6)0.0119 (2)
H34A0.562 (3)0.783 (2)0.8336 (13)0.023220
C350.86861 (12)0.82272 (10)0.86214 (7)0.0132 (2)
H35A0.845 (3)0.890 (2)0.8461 (13)0.024307
C360.63049 (13)0.91382 (10)0.85994 (7)0.0162 (2)
H36A0.658 (3)0.940 (2)0.8266 (12)0.031530
H36B0.547 (3)0.932 (2)0.8723 (16)0.031720
H36C0.683 (3)0.941 (2)0.8945 (14)0.031390
C370.59267 (15)0.77694 (11)0.92546 (7)0.0180 (3)
H37A0.515 (3)0.807 (3)0.9354 (14)0.029330
H37B0.588 (3)0.706 (2)0.9317 (13)0.027593
H37C0.645 (3)0.799 (2)0.9555 (12)0.029013
C380.97448 (13)0.78997 (12)0.83205 (7)0.0170 (2)
H38A1.032 (3)0.838 (2)0.8395 (15)0.030563
H38B0.993 (3)0.727 (2)0.8529 (14)0.028607
H38C0.963 (3)0.776 (2)0.7812 (14)0.028790
C390.87987 (14)0.82434 (12)0.92961 (7)0.0181 (3)
H39A0.942 (3)0.869 (3)0.9481 (14)0.031313
H39B0.814 (3)0.858 (2)0.9492 (13)0.030753
H39C0.875 (3)0.755 (2)0.9479 (14)0.029063
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.00868 (6)0.00822 (6)0.01140 (7)0.00034 (5)0.00037 (5)0.00001 (5)
H1A0.0435100.0312900.0235300.0068600.0032800.005010
H1B0.0464900.0293300.0228200.0027500.0005000.005040
In10.00952 (4)0.00876 (4)0.00961 (4)0.00009 (2)0.00013 (3)0.00013 (3)
P10.01007 (12)0.00966 (12)0.00844 (12)0.00076 (10)0.00067 (10)0.00063 (10)
P20.00875 (12)0.01086 (13)0.00881 (12)0.00171 (10)0.00051 (10)0.00018 (10)
P30.01108 (13)0.00768 (11)0.00877 (12)0.00026 (11)0.00057 (10)0.00083 (9)
N10.0093 (4)0.0137 (4)0.0099 (4)0.0009 (3)0.0001 (4)0.0015 (4)
N20.0119 (4)0.0122 (4)0.0099 (4)0.0018 (4)0.0013 (3)0.0024 (3)
N30.0146 (5)0.0088 (4)0.0086 (4)0.0017 (4)0.0010 (3)0.0004 (3)
N40.0107 (4)0.0090 (4)0.0073 (4)0.0011 (3)0.0013 (3)0.0002 (3)
C10.0096 (4)0.0096 (4)0.0090 (4)0.0005 (4)0.0020 (4)0.0002 (4)
C20.0144 (5)0.0136 (5)0.0115 (5)0.0001 (4)0.0031 (4)0.0002 (4)
H2A0.0275200.0322800.0198400.0011900.0013400.002790
C30.0146 (5)0.0165 (6)0.0133 (5)0.0013 (5)0.0041 (4)0.0011 (4)
H3A0.0290900.0376400.0227400.0030200.0086700.002790
C40.0113 (5)0.0155 (5)0.0169 (5)0.0009 (4)0.0038 (4)0.0009 (5)
H4A0.0186800.0421300.0309800.0034500.0045100.000090
C50.0101 (5)0.0155 (5)0.0128 (5)0.0002 (4)0.0008 (4)0.0007 (4)
H5A0.0214700.0379300.0232400.0003200.0021300.001720
C60.0096 (5)0.0108 (5)0.0097 (5)0.0006 (4)0.0014 (4)0.0004 (4)
C70.0108 (5)0.0143 (5)0.0099 (5)0.0005 (4)0.0004 (4)0.0004 (4)
H7A0.0252800.0264000.0268000.0074900.0013100.001330
H7B0.0235900.0295500.0280900.0095800.0003400.001420
C80.0154 (5)0.0160 (6)0.0112 (5)0.0014 (4)0.0020 (4)0.0006 (4)
H8A0.0232300.0207500.0250500.0005800.0011700.000360
C90.0154 (5)0.0108 (5)0.0155 (5)0.0016 (4)0.0002 (4)0.0028 (4)
H9A0.0256700.0248200.0214500.0008700.0041000.002590
C100.0161 (6)0.0298 (8)0.0222 (7)0.0002 (6)0.0083 (5)0.0036 (6)
H10A0.0288400.0279300.0405400.0077100.0005200.001030
H10B0.0241300.0380300.0293200.0006000.0026600.008090
H10C0.0261700.0506300.0254200.0011100.0073700.007580
C110.0330 (9)0.0343 (9)0.0112 (6)0.0104 (8)0.0003 (6)0.0006 (6)
H11A0.0315200.0436800.0206400.0056900.0063300.000880
H11B0.0200500.0351200.0294000.0030600.0012000.004910
H11C0.0449300.0221400.0330900.0067000.0053700.004490
C120.0250 (7)0.0121 (5)0.0187 (6)0.0007 (5)0.0016 (5)0.0025 (5)
H12A0.0469900.0163200.0305300.0026000.0020400.002380
H12B0.0245100.0300600.0301700.0080300.0051400.003150
H12C0.0271700.0395600.0235600.0038800.0076100.001800
C130.0195 (7)0.0150 (6)0.0372 (10)0.0049 (5)0.0050 (7)0.0054 (6)
H13A0.0378200.0207200.0415400.0060200.0030500.003520
H13B0.0263400.0418500.0306000.0072100.0066600.009300
H13C0.0356700.0407500.0231000.0099200.0068700.002620
C140.0123 (5)0.0086 (4)0.0089 (4)0.0016 (4)0.0001 (4)0.0012 (4)
C150.0154 (5)0.0119 (5)0.0098 (5)0.0002 (4)0.0007 (4)0.0018 (4)
H15A0.0287800.0260000.0241700.0029600.0073100.000950
C160.0195 (6)0.0131 (5)0.0133 (5)0.0009 (5)0.0012 (4)0.0056 (4)
H16A0.0375300.0270500.0240000.0007900.0061300.008930
C170.0179 (6)0.0124 (5)0.0172 (6)0.0032 (5)0.0003 (5)0.0049 (4)
H17A0.0394200.0222300.0316600.0088800.0038500.008260
C180.0146 (5)0.0121 (5)0.0160 (5)0.0029 (4)0.0008 (4)0.0040 (4)
H18A0.0306000.0259300.0270700.0081600.0072500.002870
C190.0106 (5)0.0109 (5)0.0097 (4)0.0005 (4)0.0003 (4)0.0022 (4)
C200.0107 (5)0.0131 (5)0.0117 (5)0.0032 (4)0.0017 (4)0.0016 (4)
H20A0.0328600.0190400.0284900.0004000.0031500.001870
H20B0.0195400.0351900.0280400.0056100.0024200.004490
C210.0129 (5)0.0161 (6)0.0113 (5)0.0036 (4)0.0007 (4)0.0011 (4)
H21A0.0219600.0281600.0280900.0075400.0006400.004060
C220.0095 (4)0.0155 (5)0.0120 (5)0.0005 (4)0.0009 (4)0.0021 (4)
H22A0.0235700.0249900.0220000.0002800.0004600.005630
C230.0213 (7)0.0220 (7)0.0175 (6)0.0002 (6)0.0027 (5)0.0070 (5)
H23A0.0344900.0293400.0350800.0048800.0105700.010790
H23B0.0375100.0280300.0255800.0036200.0039100.006420
H23C0.0281400.0247300.0367400.0043100.0087000.003240
C240.0244 (7)0.0213 (7)0.0102 (5)0.0060 (6)0.0030 (5)0.0013 (5)
H24A0.0277700.0310000.0314800.0072500.0025600.003080
H24B0.0401700.0303700.0284700.0086100.0133600.001160
H24C0.0213400.0357400.0310600.0055900.0017700.009410
C250.0167 (5)0.0196 (6)0.0156 (6)0.0027 (4)0.0016 (5)0.0025 (5)
H25A0.0276300.0373200.0301400.0143300.0001500.003440
H25B0.0208200.0364900.0279400.0065800.0009800.002290
H25C0.0425100.0278400.0229300.0030900.0004500.008420
C260.0104 (5)0.0222 (7)0.0187 (6)0.0020 (5)0.0011 (4)0.0027 (5)
H26A0.0200900.0380600.0447800.0038100.0035300.000420
H26B0.0283900.0382100.0359800.0068200.0037800.017430
H26C0.0282000.0471800.0250000.0092600.0036500.001410
C270.0143 (5)0.0092 (4)0.0079 (4)0.0017 (4)0.0008 (4)0.0000 (4)
C280.0210 (6)0.0128 (5)0.0095 (5)0.0039 (5)0.0024 (4)0.0012 (4)
H28A0.0352700.0235000.0219200.0056100.0010600.005320
C290.0270 (7)0.0173 (6)0.0104 (5)0.0080 (5)0.0059 (5)0.0007 (4)
H29A0.0417200.0335200.0168300.0083300.0049200.000220
C300.0244 (7)0.0151 (6)0.0114 (5)0.0081 (5)0.0036 (5)0.0008 (4)
H30A0.0459900.0266300.0246600.0140400.0032800.004410
C310.0180 (6)0.0112 (5)0.0109 (5)0.0047 (4)0.0008 (4)0.0006 (4)
H31A0.0405500.0210300.0231500.0080900.0004800.002870
C320.0122 (5)0.0094 (4)0.0096 (4)0.0015 (4)0.0007 (4)0.0005 (3)
C330.0160 (5)0.0084 (4)0.0104 (5)0.0011 (4)0.0003 (4)0.0006 (4)
H33A0.0244300.0284700.0251800.0084000.0017300.000760
H33B0.0345700.0185100.0267500.0054400.0035900.000060
C340.0141 (5)0.0111 (5)0.0104 (5)0.0008 (4)0.0005 (4)0.0006 (4)
H34A0.0233700.0247800.0215100.0010200.0031900.002490
C350.0149 (5)0.0109 (5)0.0139 (5)0.0019 (4)0.0005 (4)0.0018 (4)
H35A0.0314100.0167400.0247700.0001500.0015600.001140
C360.0198 (6)0.0121 (5)0.0167 (6)0.0031 (5)0.0016 (5)0.0005 (4)
H36A0.0474600.0250800.0220500.0009700.0076600.002680
H36B0.0286200.0261100.0404300.0086100.0044000.001850
H36C0.0402400.0247400.0291900.0020500.0098300.003550
C370.0237 (7)0.0167 (6)0.0135 (5)0.0009 (5)0.0042 (5)0.0008 (5)
H37A0.0243600.0352300.0284000.0100100.0052000.000630
H37B0.0373900.0178300.0275600.0021100.0033600.000510
H37C0.0287700.0360300.0222400.0073000.0054400.001870
C380.0153 (6)0.0185 (6)0.0172 (6)0.0046 (5)0.0014 (5)0.0035 (5)
H38A0.0263200.0255400.0398300.0112000.0045300.006930
H38B0.0313100.0229000.0316100.0037200.0046800.007450
H38C0.0308500.0371800.0183400.0010600.0000700.004390
C390.0192 (6)0.0201 (6)0.0150 (6)0.0031 (5)0.0030 (5)0.0043 (5)
H39A0.0294000.0365900.0279500.0138700.0023700.003670
H39B0.0317700.0347200.0257700.0089700.0045800.004320
H39C0.0428700.0185400.0257800.0026000.0010700.002650
Geometric parameters (Å, º) top
Ni1—H1A1.68 (4)C14—C191.4306 (19)
Ni1—H1B1.68 (4)C15—H15A1.17 (3)
Ni1—In12.4790 (2)C15—C161.397 (2)
Ni1—P12.2836 (4)C16—H16A1.10 (3)
Ni1—P22.2530 (4)C16—C171.395 (2)
Ni1—P32.2505 (4)C17—H17A1.15 (3)
H1A—H1B0.94 (5)C17—C181.392 (2)
In1—N12.1121 (11)C18—H18A1.08 (3)
In1—N22.1230 (12)C18—C191.414 (2)
In1—N32.1131 (12)C20—H20A1.15 (3)
In1—N42.3666 (11)C20—H20B1.11 (3)
P1—C71.8643 (14)C21—H21A1.12 (3)
P1—C81.8696 (15)C21—C231.530 (2)
P1—C91.8636 (15)C21—C241.535 (2)
P2—C201.8708 (14)C22—H22A1.11 (3)
P2—C211.8599 (14)C22—C251.527 (2)
P2—C221.8780 (14)C22—C261.533 (2)
P3—C331.8888 (14)C23—H23A1.10 (3)
P3—C341.8664 (14)C23—H23B1.16 (3)
P3—C351.8554 (15)C23—H23C1.09 (3)
N1—C61.3662 (18)C24—H24A1.19 (3)
N1—C71.4408 (19)C24—H24B1.03 (3)
N2—C191.3652 (17)C24—H24C1.09 (3)
N2—C201.4492 (18)C25—H25A1.08 (3)
N3—C321.3712 (17)C25—H25B1.03 (3)
N3—C331.4395 (17)C25—H25C1.10 (3)
N4—C11.4634 (17)C26—H26A1.10 (3)
N4—C141.4561 (17)C26—H26B1.08 (3)
N4—C271.4641 (17)C26—H26C1.08 (3)
C1—C21.3861 (19)C27—C281.3858 (19)
C1—C61.4313 (19)C27—C321.4264 (19)
C2—H2A1.03 (3)C28—H28A1.12 (3)
C2—C31.403 (2)C28—C291.400 (2)
C3—H3A1.03 (3)C29—H29A1.03 (3)
C3—C41.397 (2)C29—C301.390 (2)
C4—H4A1.01 (3)C30—H30A1.22 (3)
C4—C51.394 (2)C30—C311.393 (2)
C5—H5A1.07 (3)C31—H31A0.97 (3)
C5—C61.414 (2)C31—C321.4098 (19)
C7—H7A1.06 (3)C33—H33A1.13 (3)
C7—H7B1.12 (3)C33—H33B1.09 (3)
C8—H8A1.07 (3)C34—H34A1.11 (3)
C8—C101.533 (2)C34—C361.531 (2)
C8—C111.532 (2)C34—C371.534 (2)
C9—H9A1.12 (3)C35—H35A1.08 (3)
C9—C121.537 (2)C35—C381.536 (2)
C9—C131.522 (2)C35—C391.528 (2)
C10—H10A1.16 (3)C36—H36A0.91 (3)
C10—H10B1.01 (3)C36—H36B1.09 (3)
C10—H10C1.26 (3)C36—H36C1.08 (3)
C11—H11A1.06 (3)C37—H37A1.07 (3)
C11—H11B1.06 (3)C37—H37B1.04 (3)
C11—H11C1.09 (3)C37—H37C0.98 (3)
C12—H12A1.05 (3)C38—H38A1.01 (3)
C12—H12B1.20 (3)C38—H38B1.06 (3)
C12—H12C1.05 (3)C38—H38C1.17 (3)
C13—H13A1.07 (3)C39—H39A1.09 (3)
C13—H13B1.10 (3)C39—H39B1.04 (3)
C13—H13C0.95 (3)C39—H39C1.09 (3)
C14—C151.3872 (18)
H1B—Ni1—H1A32.5 (17)C15—C14—N4121.36 (12)
In1—Ni1—H1A154.5 (14)C19—C14—N4117.98 (11)
In1—Ni1—H1B171.5 (15)C19—C14—C15120.62 (12)
P1—Ni1—H1A85.1 (15)H15A—C15—C14116.4 (16)
P1—Ni1—H1B97.5 (16)C16—C15—C14121.61 (13)
P1—Ni1—In181.128 (10)C16—C15—H15A121.9 (16)
P2—Ni1—H1A87.3 (14)H16A—C16—C15119.2 (18)
P2—Ni1—H1B105.2 (16)C17—C16—C15118.50 (13)
P2—Ni1—In182.380 (10)C17—C16—H16A122.0 (17)
P2—Ni1—P1122.749 (15)H17A—C17—C16117.3 (17)
P3—Ni1—H1A121.0 (14)C18—C17—C16120.88 (13)
P3—Ni1—H1B88.9 (14)C18—C17—H17A121.4 (17)
P3—Ni1—In184.544 (10)H18A—C18—C17120.8 (17)
P3—Ni1—P1120.197 (15)C19—C18—C17121.59 (14)
P3—Ni1—P2112.156 (15)C19—C18—H18A117.4 (17)
H1B—H1A—Ni174 (4)C14—C19—N2118.78 (12)
H1A—H1B—Ni174 (4)C18—C19—N2124.40 (13)
N1—In1—Ni1104.59 (3)C18—C19—C14116.81 (12)
N2—In1—Ni1102.78 (3)N2—C20—P2108.31 (9)
N2—In1—N1116.51 (5)H20A—C20—P2109.2 (16)
N3—In1—Ni1103.27 (3)H20A—C20—N2113.7 (16)
N3—In1—N1111.74 (5)H20B—C20—P2110.4 (16)
N3—In1—N2115.82 (5)H20B—C20—N2110.2 (16)
N4—In1—Ni1178.62 (3)H20B—C20—H20A105 (3)
N4—In1—N176.66 (4)H21A—C21—P2106.5 (16)
N4—In1—N276.06 (4)C23—C21—P2112.34 (10)
N4—In1—N376.69 (4)C23—C21—H21A107.8 (17)
C7—P1—Ni1117.43 (5)C24—C21—P2110.09 (11)
C8—P1—Ni1110.59 (5)C24—C21—H21A109.8 (16)
C8—P1—C7103.27 (7)C24—C21—C23110.18 (13)
C9—P1—Ni1116.66 (5)H22A—C22—P2104.5 (16)
C9—P1—C7102.06 (7)C25—C22—P2111.05 (10)
C9—P1—C8105.32 (7)C25—C22—H22A108.8 (16)
C20—P2—Ni1118.05 (5)C26—C22—P2115.67 (11)
C21—P2—Ni1114.34 (5)C26—C22—H22A107.6 (17)
C21—P2—C20102.58 (6)C26—C22—C25108.98 (12)
C22—P2—Ni1117.32 (5)H23A—C23—C21109.8 (19)
C22—P2—C20100.53 (6)H23B—C23—C21111.8 (17)
C22—P2—C21101.47 (7)H23B—C23—H23A105 (2)
C33—P3—Ni1118.80 (4)H23C—C23—C21108.4 (18)
C34—P3—Ni1112.77 (5)H23C—C23—H23A106 (3)
C34—P3—C3399.12 (6)H23C—C23—H23B116 (3)
C35—P3—Ni1118.80 (5)H24A—C24—C21109.2 (17)
C35—P3—C3399.75 (6)H24B—C24—C21108.9 (18)
C35—P3—C34104.84 (6)H24B—C24—H24A110 (3)
C6—N1—In1112.91 (9)H24C—C24—C21114.5 (17)
C7—N1—In1115.74 (9)H24C—C24—H24A106 (3)
C7—N1—C6119.59 (11)H24C—C24—H24B108 (3)
C19—N2—In1113.03 (9)H25A—C25—C22113.4 (17)
C20—N2—In1117.98 (8)H25B—C25—C22118.0 (17)
C20—N2—C19120.74 (12)H25B—C25—H25A105 (3)
C32—N3—In1113.18 (9)H25C—C25—C22104.7 (17)
C33—N3—In1118.75 (8)H25C—C25—H25A111 (3)
C33—N3—C32119.57 (11)H25C—C25—H25B104 (3)
C1—N4—In1103.26 (8)H26A—C26—C22112.8 (18)
C14—N4—In1103.49 (8)H26B—C26—C22109.8 (18)
C14—N4—C1115.85 (10)H26B—C26—H26A112 (3)
C27—N4—In1102.60 (7)H26C—C26—C22120.5 (18)
C27—N4—C1113.63 (11)H26C—C26—H26A96 (3)
C27—N4—C14115.54 (10)H26C—C26—H26B105 (3)
C2—C1—N4121.42 (12)C28—C27—N4121.00 (12)
C6—C1—N4117.91 (11)C32—C27—N4117.92 (11)
C6—C1—C2120.59 (12)C32—C27—C28121.07 (12)
H2A—C2—C1116.8 (17)H28A—C28—C27118.5 (16)
C3—C2—C1121.51 (14)C29—C28—C27121.07 (13)
C3—C2—H2A121.6 (17)C29—C28—H28A120.2 (17)
H3A—C3—C2134.0 (19)H29A—C29—C28116.4 (17)
C4—C3—C2118.55 (13)C30—C29—C28118.62 (13)
C4—C3—H3A107.3 (19)C30—C29—H29A124.7 (17)
H4A—C4—C3118.1 (18)H30A—C30—C29113.5 (17)
C5—C4—C3120.75 (13)C31—C30—C29120.93 (13)
C5—C4—H4A121.1 (18)C31—C30—H30A125.5 (17)
H5A—C5—C4118.0 (17)H31A—C31—C30110.1 (17)
C6—C5—C4121.57 (13)C32—C31—C30121.55 (13)
C6—C5—H5A120.4 (17)C32—C31—H31A128.2 (17)
C1—C6—N1119.20 (12)C27—C32—N3119.29 (11)
C5—C6—N1123.77 (13)C31—C32—N3124.02 (12)
C5—C6—C1117.02 (12)C31—C32—C27116.69 (11)
N1—C7—P1108.70 (9)N3—C33—P3111.64 (9)
H7A—C7—P1103.4 (17)H33A—C33—P3103.5 (16)
H7A—C7—N1115.7 (16)H33A—C33—N3110.7 (16)
H7B—C7—P1110.8 (16)H33B—C33—P3107.8 (15)
H7B—C7—N1112.0 (16)H33B—C33—N3109.7 (15)
H7B—C7—H7A106 (2)H33B—C33—H33A113 (2)
H8A—C8—P1101.6 (15)H34A—C34—P3103.6 (16)
C10—C8—P1117.29 (12)C36—C34—P3114.81 (10)
C10—C8—H8A104.5 (16)C36—C34—H34A108.9 (16)
C11—C8—P1110.37 (11)C37—C34—P3113.49 (10)
C11—C8—H8A111.2 (16)C37—C34—H34A104.4 (16)
C11—C8—C10111.24 (15)C37—C34—C36110.70 (12)
H9A—C9—P1104.8 (17)H35A—C35—P3101.5 (17)
C12—C9—P1109.98 (10)C38—C35—P3108.57 (10)
C12—C9—H9A108.3 (16)C38—C35—H35A111.1 (16)
C13—C9—P1116.87 (12)C39—C35—P3113.42 (11)
C13—C9—H9A107.8 (16)C39—C35—H35A110.2 (16)
C13—C9—C12108.75 (14)C39—C35—C38111.66 (13)
H10A—C10—C8113.9 (18)H36A—C36—C34118.4 (19)
H10B—C10—C8118.9 (18)H36B—C36—C34102.3 (19)
H10B—C10—H10A103 (3)H36B—C36—H36A117 (3)
H10C—C10—C8103.7 (17)H36C—C36—C34109.6 (18)
H10C—C10—H10A105 (3)H36C—C36—H36A103 (3)
H10C—C10—H10B112 (3)H36C—C36—H36B106 (3)
H11A—C11—C899.9 (18)H37A—C37—C34108.3 (18)
H11B—C11—C8119.7 (17)H37B—C37—C34115.9 (16)
H11B—C11—H11A118 (3)H37B—C37—H37A109 (3)
H11C—C11—C8110.2 (17)H37C—C37—C34110.4 (18)
H11C—C11—H11A105 (3)H37C—C37—H37A107 (3)
H11C—C11—H11B104 (3)H37C—C37—H37B106 (3)
H12A—C12—C9103.3 (17)H38A—C38—C35107.2 (19)
H12B—C12—C9108.9 (16)H38B—C38—C35104.4 (17)
H12B—C12—H12A111 (3)H38B—C38—H38A113 (3)
H12C—C12—C9107.3 (18)H38C—C38—C35112.4 (17)
H12C—C12—H12A112 (3)H38C—C38—H38A111 (3)
H12C—C12—H12B114 (2)H38C—C38—H38B108 (2)
H13A—C13—C9112.3 (19)H39A—C39—C35117.0 (17)
H13B—C13—C9113.3 (17)H39B—C39—C35111.2 (17)
H13B—C13—H13A116 (3)H39B—C39—H39A95 (3)
H13C—C13—C9122 (2)H39C—C39—C35110.9 (17)
H13C—C13—H13A98 (3)H39C—C39—H39A116 (3)
H13C—C13—H13B93 (3)H39C—C39—H39B104 (3)
(GOJNIF_IAM_0_HADPs) top
Crystal data top
C39H62InN4NiP3Dx = 1.415 Mg m3
Mr = 853.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9537 reflections
a = 12.2127 (4) Åθ = 2.3–36.4°
b = 14.5402 (5) ŵ = 1.20 mm1
c = 22.5601 (8) ÅT = 100 K
V = 4006.1 (2) Å3Block, gold
Z = 40.14 × 0.08 × 0.06 mm
F(000) = 105.805
Data collection top
Bruker Photon-II CMOS
diffractometer
18741 reflections with I 2u(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
SADABS. R.Blessing, 1995
θmax = 36.4°, θmin = 2.3°
Tmin = 0.701, Tmax = 0.747h = 2020
237431 measured reflectionsk = 2424
19473 independent reflectionsl = 3737
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullOnly H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.019 w = 1/[σ2(Fo2) + (0.0146P)2 + 1.8877P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.043(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.40 e Å3
19473 reflectionsΔρmin = 0.59 e Å3
619 parametersAbsolute structure: Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.
0 restraintsAbsolute structure parameter: 0.0095 (17)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.755796 (11)0.598654 (9)0.856163 (6)0.00938 (2)
Ha0.7260 (11)0.5766 (10)0.9247 (6)0.000000
Hb0.7616 (12)0.6325 (10)0.9232 (6)0.000000
In10.798243 (5)0.580828 (4)0.749323 (3)0.008341 (12)
P10.91843 (2)0.522271 (19)0.864329 (12)0.00938 (4)
P20.59907 (2)0.528580 (19)0.829182 (12)0.00943 (4)
P30.75361 (2)0.750090 (18)0.835685 (11)0.00916 (4)
N10.96160 (7)0.53379 (6)0.74726 (5)0.01061 (13)
N20.67672 (8)0.48679 (7)0.72033 (4)0.01127 (15)
N30.78431 (8)0.71619 (6)0.71614 (4)0.01044 (14)
N40.83419 (7)0.56338 (6)0.64690 (4)0.00869 (13)
C10.95366 (8)0.57172 (7)0.64335 (4)0.00937 (15)
C21.00532 (9)0.59715 (8)0.59114 (5)0.01291 (17)
H20.9638 (12)0.6087 (10)0.5560 (6)0.000000
C31.11899 (10)0.60859 (8)0.58844 (5)0.01473 (18)
H31.1552 (12)0.6248 (10)0.5549 (6)0.000000
C41.18023 (8)0.59547 (8)0.63980 (5)0.01397 (17)
H41.2595 (12)0.6040 (9)0.6371 (6)0.000000
C51.12981 (9)0.57034 (8)0.69260 (5)0.01243 (17)
H51.1718 (12)0.5611 (10)0.7277 (6)0.000000
C61.01545 (9)0.55745 (7)0.69632 (5)0.00990 (17)
C71.01944 (9)0.53673 (8)0.80313 (5)0.01138 (18)
H7a1.0596 (11)0.5917 (10)0.8101 (6)0.000000
H7b1.0756 (12)0.4873 (10)0.8052 (6)0.000000
C80.99542 (10)0.56229 (8)0.93126 (5)0.01418 (18)
H80.9810 (12)0.6279 (10)0.9307 (6)0.000000
C90.91074 (9)0.39460 (8)0.87149 (5)0.01383 (18)
H90.8587 (12)0.3840 (10)0.9047 (6)0.000000
C101.12032 (11)0.55057 (11)0.93042 (6)0.0226 (2)
H10a1.1474 (12)0.4853 (10)0.9273 (6)0.000000
H10b1.1541 (11)0.5828 (10)0.8977 (6)0.000000
H10c1.1500 (11)0.5776 (10)0.9682 (6)0.000000
C110.94528 (14)0.52142 (12)0.98763 (6)0.0266 (3)
H11a0.9790 (12)0.5480 (10)1.0205 (6)0.000000
H11b0.8705 (12)0.5358 (10)0.9904 (6)0.000000
H11c0.9546 (12)0.4534 (10)0.9897 (6)0.000000
C120.86458 (12)0.35268 (8)0.81442 (6)0.0186 (2)
H12a0.8499 (12)0.2888 (10)0.8206 (6)0.000000
H12b0.7919 (12)0.3829 (9)0.8026 (6)0.000000
H12c0.9179 (12)0.3589 (10)0.7842 (6)0.000000
C131.01693 (12)0.34496 (9)0.88757 (7)0.0235 (3)
H13a1.0043 (12)0.2815 (10)0.8878 (6)0.000000
H13b1.0744 (12)0.3595 (10)0.8592 (6)0.000000
H13c1.0462 (12)0.3642 (10)0.9247 (6)0.000000
C140.78952 (9)0.47270 (7)0.63327 (4)0.00998 (15)
C150.82592 (9)0.42270 (8)0.58481 (4)0.01227 (16)
H150.8836 (12)0.4444 (10)0.5618 (6)0.000000
C160.78510 (10)0.33494 (8)0.57256 (5)0.01507 (19)
H160.8128 (12)0.2976 (10)0.5388 (6)0.000000
C170.70729 (11)0.29763 (8)0.61045 (5)0.01581 (18)
H170.6801 (11)0.2367 (10)0.6039 (6)0.000000
C180.67000 (10)0.34622 (8)0.65958 (5)0.01406 (18)
H180.6192 (12)0.3160 (10)0.6869 (6)0.000000
C190.70909 (9)0.43555 (7)0.67262 (4)0.01031 (15)
C200.60325 (9)0.44849 (8)0.76424 (5)0.01193 (17)
H20a0.6229 (12)0.3866 (10)0.7792 (6)0.000000
H20b0.5268 (10)0.4402 (9)0.7488 (7)0.000000
C210.53629 (9)0.45614 (8)0.88800 (5)0.01311 (18)
H210.4724 (11)0.4263 (10)0.8704 (6)0.000000
C220.48061 (9)0.60404 (8)0.80768 (5)0.01231 (17)
H220.4805 (12)0.6529 (10)0.8376 (6)0.000000
C230.61392 (11)0.38123 (9)0.91002 (6)0.0204 (2)
H23a0.5759 (12)0.3410 (10)0.9388 (6)0.000000
H23b0.6378 (12)0.3428 (10)0.8778 (6)0.000000
H23c0.6770 (11)0.4090 (10)0.9298 (6)0.000000
C240.49921 (11)0.51660 (9)0.93994 (5)0.0185 (2)
H24a0.4497 (12)0.5635 (10)0.9286 (6)0.000000
H24b0.4687 (12)0.4794 (10)0.9690 (6)0.000000
H24c0.5593 (12)0.5461 (10)0.9591 (6)0.000000
C250.49935 (9)0.64746 (8)0.74666 (7)0.01698 (18)
H25a0.4425 (11)0.6918 (9)0.7375 (6)0.000000
H25b0.5700 (11)0.6763 (9)0.7413 (6)0.000000
H25c0.4961 (12)0.6020 (10)0.7172 (6)0.000000
C260.36768 (10)0.55817 (9)0.80855 (6)0.0171 (2)
H26a0.3129 (12)0.6050 (10)0.7982 (6)0.000000
H26b0.3643 (12)0.5087 (10)0.7808 (6)0.000000
H26c0.3479 (12)0.5374 (10)0.8454 (6)0.000000
C270.77592 (8)0.64147 (7)0.62070 (4)0.01026 (16)
C280.74247 (11)0.64021 (8)0.56208 (5)0.01440 (18)
H280.7563 (12)0.5835 (10)0.5378 (6)0.000000
C290.69203 (11)0.71654 (8)0.53624 (5)0.0178 (2)
H290.6722 (12)0.7142 (10)0.4980 (6)0.000000
C300.67556 (11)0.79426 (8)0.57074 (5)0.0168 (2)
H300.6443 (12)0.8474 (10)0.5552 (6)0.000000
C310.70535 (10)0.79577 (7)0.63025 (5)0.01299 (17)
H310.6925 (12)0.8500 (9)0.6531 (6)0.000000
C320.75538 (9)0.71943 (7)0.65745 (4)0.00976 (15)
C330.74807 (9)0.78807 (6)0.75562 (5)0.01182 (15)
H33a0.6711 (10)0.8065 (9)0.7486 (7)0.000000
H33b0.7900 (10)0.8442 (9)0.7526 (7)0.000000
C340.62759 (9)0.80863 (7)0.86334 (5)0.01205 (17)
H340.5705 (12)0.7876 (10)0.8375 (6)0.000000
C350.86862 (9)0.82265 (7)0.86207 (5)0.01288 (17)
H350.8529 (12)0.8830 (10)0.8478 (6)0.000000
C360.63057 (10)0.91388 (8)0.85995 (5)0.01597 (18)
H36a0.6544 (12)0.9338 (10)0.8233 (6)0.000000
H36b0.5567 (12)0.9378 (10)0.8681 (6)0.000000
H36c0.6828 (12)0.9408 (10)0.8923 (6)0.000000
C370.59279 (11)0.77702 (9)0.92533 (5)0.0175 (2)
H37a0.5197 (12)0.8037 (10)0.9330 (6)0.000000
H37b0.5874 (12)0.7113 (10)0.9283 (6)0.000000
H37c0.6426 (12)0.7981 (10)0.9529 (6)0.000000
C380.97439 (10)0.78989 (9)0.83202 (6)0.0168 (2)
H38a1.0297 (12)0.8332 (10)0.8362 (6)0.000000
H38b1.0001 (12)0.7363 (10)0.8487 (6)0.000000
H38c0.9622 (12)0.7786 (10)0.7889 (6)0.000000
C390.87992 (11)0.82439 (9)0.92961 (6)0.0178 (2)
H39a0.9476 (12)0.8487 (10)0.9422 (6)0.000000
H39b0.8237 (12)0.8581 (10)0.9478 (6)0.000000
H39c0.8745 (12)0.7591 (10)0.9474 (6)0.000000
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.00867 (5)0.00828 (5)0.01119 (5)0.00038 (4)0.00040 (4)0.00007 (4)
Ha0.0000000.0000000.0000000.0000000.0000000.000000
Hb0.0000000.0000000.0000000.0000000.0000000.000000
In10.00852 (2)0.00788 (2)0.00862 (2)0.000100 (19)0.00017 (2)0.00012 (2)
P10.01020 (10)0.00953 (10)0.00842 (10)0.00072 (8)0.00059 (8)0.00063 (8)
P20.00868 (10)0.01080 (10)0.00882 (10)0.00174 (8)0.00042 (8)0.00031 (8)
P30.01096 (10)0.00781 (9)0.00872 (9)0.00021 (9)0.00060 (9)0.00076 (8)
N10.0093 (3)0.0139 (3)0.0087 (3)0.0010 (2)0.0003 (3)0.0009 (3)
N20.0117 (4)0.0123 (4)0.0099 (3)0.0024 (3)0.0017 (3)0.0025 (3)
N30.0145 (4)0.0090 (3)0.0079 (3)0.0016 (3)0.0004 (3)0.0003 (3)
N40.0097 (3)0.0080 (3)0.0083 (3)0.0007 (3)0.0009 (3)0.0003 (3)
C10.0097 (3)0.0090 (4)0.0094 (4)0.0003 (3)0.0012 (3)0.0004 (3)
C20.0152 (4)0.0123 (4)0.0112 (4)0.0005 (3)0.0023 (3)0.0001 (3)
H20.0000000.0000000.0000000.0000000.0000000.000000
C30.0156 (5)0.0146 (4)0.0139 (4)0.0006 (4)0.0048 (4)0.0009 (4)
H30.0000000.0000000.0000000.0000000.0000000.000000
C40.0116 (4)0.0134 (4)0.0169 (4)0.0009 (3)0.0035 (3)0.0001 (4)
H40.0000000.0000000.0000000.0000000.0000000.000000
C50.0103 (4)0.0139 (4)0.0131 (4)0.0004 (3)0.0001 (3)0.0001 (3)
H50.0000000.0000000.0000000.0000000.0000000.000000
C60.0101 (4)0.0096 (4)0.0100 (4)0.0009 (3)0.0012 (3)0.0006 (3)
C70.0104 (4)0.0138 (4)0.0099 (4)0.0009 (3)0.0005 (3)0.0008 (3)
H7a0.0000000.0000000.0000000.0000000.0000000.000000
H7b0.0000000.0000000.0000000.0000000.0000000.000000
C80.0154 (5)0.0163 (5)0.0109 (4)0.0013 (4)0.0024 (3)0.0005 (3)
H80.0000000.0000000.0000000.0000000.0000000.000000
C90.0150 (4)0.0105 (4)0.0160 (4)0.0013 (3)0.0005 (3)0.0026 (3)
H90.0000000.0000000.0000000.0000000.0000000.000000
C100.0169 (5)0.0296 (6)0.0215 (6)0.0003 (5)0.0080 (4)0.0037 (5)
H10a0.0000000.0000000.0000000.0000000.0000000.000000
H10b0.0000000.0000000.0000000.0000000.0000000.000000
H10c0.0000000.0000000.0000000.0000000.0000000.000000
C110.0341 (7)0.0340 (7)0.0116 (5)0.0099 (6)0.0002 (5)0.0009 (5)
H11a0.0000000.0000000.0000000.0000000.0000000.000000
H11b0.0000000.0000000.0000000.0000000.0000000.000000
H11c0.0000000.0000000.0000000.0000000.0000000.000000
C120.0252 (6)0.0106 (4)0.0201 (5)0.0008 (4)0.0017 (4)0.0022 (4)
H12a0.0000000.0000000.0000000.0000000.0000000.000000
H12b0.0000000.0000000.0000000.0000000.0000000.000000
H12c0.0000000.0000000.0000000.0000000.0000000.000000
C130.0198 (6)0.0146 (5)0.0361 (7)0.0053 (4)0.0061 (5)0.0049 (5)
H13a0.0000000.0000000.0000000.0000000.0000000.000000
H13b0.0000000.0000000.0000000.0000000.0000000.000000
H13c0.0000000.0000000.0000000.0000000.0000000.000000
C140.0120 (4)0.0087 (3)0.0092 (4)0.0015 (3)0.0012 (3)0.0011 (3)
C150.0147 (4)0.0123 (4)0.0097 (4)0.0007 (3)0.0005 (3)0.0012 (3)
H150.0000000.0000000.0000000.0000000.0000000.000000
C160.0182 (5)0.0134 (4)0.0136 (4)0.0001 (4)0.0001 (4)0.0056 (3)
H160.0000000.0000000.0000000.0000000.0000000.000000
C170.0180 (5)0.0121 (4)0.0173 (5)0.0023 (4)0.0007 (4)0.0051 (3)
H170.0000000.0000000.0000000.0000000.0000000.000000
C180.0138 (4)0.0123 (4)0.0160 (5)0.0029 (3)0.0008 (4)0.0032 (3)
H180.0000000.0000000.0000000.0000000.0000000.000000
C190.0103 (4)0.0105 (4)0.0101 (4)0.0000 (3)0.0009 (3)0.0020 (3)
C200.0113 (4)0.0125 (4)0.0120 (4)0.0026 (3)0.0015 (3)0.0020 (3)
H20a0.0000000.0000000.0000000.0000000.0000000.000000
H20b0.0000000.0000000.0000000.0000000.0000000.000000
C210.0129 (4)0.0157 (4)0.0108 (4)0.0040 (3)0.0009 (3)0.0011 (3)
H210.0000000.0000000.0000000.0000000.0000000.000000
C220.0098 (4)0.0155 (4)0.0116 (4)0.0005 (3)0.0003 (3)0.0019 (3)
H220.0000000.0000000.0000000.0000000.0000000.000000
C230.0202 (5)0.0221 (6)0.0189 (5)0.0003 (4)0.0026 (4)0.0077 (4)
H23a0.0000000.0000000.0000000.0000000.0000000.000000
H23b0.0000000.0000000.0000000.0000000.0000000.000000
H23c0.0000000.0000000.0000000.0000000.0000000.000000
C240.0235 (6)0.0215 (5)0.0105 (4)0.0057 (4)0.0030 (4)0.0012 (4)
H24a0.0000000.0000000.0000000.0000000.0000000.000000
H24b0.0000000.0000000.0000000.0000000.0000000.000000
H24c0.0000000.0000000.0000000.0000000.0000000.000000
C250.0171 (4)0.0188 (4)0.0150 (5)0.0027 (3)0.0009 (4)0.0026 (5)
H25a0.0000000.0000000.0000000.0000000.0000000.000000
H25b0.0000000.0000000.0000000.0000000.0000000.000000
H25c0.0000000.0000000.0000000.0000000.0000000.000000
C260.0104 (4)0.0224 (5)0.0185 (5)0.0012 (4)0.0010 (4)0.0032 (4)
H26a0.0000000.0000000.0000000.0000000.0000000.000000
H26b0.0000000.0000000.0000000.0000000.0000000.000000
H26c0.0000000.0000000.0000000.0000000.0000000.000000
C270.0131 (4)0.0090 (4)0.0087 (4)0.0014 (3)0.0004 (3)0.0007 (3)
C280.0196 (5)0.0136 (4)0.0099 (4)0.0038 (4)0.0029 (4)0.0012 (3)
H280.0000000.0000000.0000000.0000000.0000000.000000
C290.0249 (6)0.0179 (5)0.0107 (4)0.0076 (4)0.0054 (4)0.0002 (4)
H290.0000000.0000000.0000000.0000000.0000000.000000
C300.0223 (5)0.0162 (5)0.0118 (4)0.0076 (4)0.0025 (4)0.0018 (4)
H300.0000000.0000000.0000000.0000000.0000000.000000
C310.0164 (4)0.0117 (4)0.0109 (4)0.0038 (4)0.0006 (4)0.0005 (3)
H310.0000000.0000000.0000000.0000000.0000000.000000
C320.0108 (4)0.0094 (3)0.0090 (4)0.0006 (3)0.0004 (3)0.0003 (3)
C330.0162 (4)0.0087 (3)0.0106 (4)0.0015 (3)0.0004 (4)0.0005 (3)
H33a0.0000000.0000000.0000000.0000000.0000000.000000
H33b0.0000000.0000000.0000000.0000000.0000000.000000
C340.0139 (4)0.0113 (4)0.0109 (4)0.0013 (3)0.0003 (3)0.0012 (3)
H340.0000000.0000000.0000000.0000000.0000000.000000
C350.0143 (4)0.0107 (4)0.0136 (4)0.0024 (3)0.0004 (3)0.0015 (3)
H350.0000000.0000000.0000000.0000000.0000000.000000
C360.0203 (5)0.0110 (4)0.0166 (4)0.0034 (4)0.0009 (4)0.0010 (4)
H36a0.0000000.0000000.0000000.0000000.0000000.000000
H36b0.0000000.0000000.0000000.0000000.0000000.000000
H36c0.0000000.0000000.0000000.0000000.0000000.000000
C370.0220 (5)0.0173 (5)0.0133 (5)0.0013 (4)0.0039 (4)0.0003 (4)
H37a0.0000000.0000000.0000000.0000000.0000000.000000
H37b0.0000000.0000000.0000000.0000000.0000000.000000
H37c0.0000000.0000000.0000000.0000000.0000000.000000
C380.0146 (5)0.0179 (5)0.0179 (5)0.0037 (4)0.0013 (4)0.0029 (4)
H38a0.0000000.0000000.0000000.0000000.0000000.000000
H38b0.0000000.0000000.0000000.0000000.0000000.000000
H38c0.0000000.0000000.0000000.0000000.0000000.000000
C390.0191 (5)0.0199 (5)0.0143 (5)0.0027 (4)0.0026 (4)0.0042 (4)
H39a0.0000000.0000000.0000000.0000000.0000000.000000
H39b0.0000000.0000000.0000000.0000000.0000000.000000
H39c0.0000000.0000000.0000000.0000000.0000000.000000
Geometric parameters (Å, º) top
Ni1—Ha1.620 (14)C14—C191.4298 (15)
Ni1—Hb1.593 (14)C15—H150.931 (14)
Ni1—In12.4790 (2)C15—C161.3976 (16)
Ni1—P12.2831 (3)C16—H160.995 (14)
Ni1—P22.2521 (3)C16—C171.3885 (17)
Ni1—P32.2500 (3)C17—H170.958 (14)
Ha—Hb0.922 (18)C17—C181.3910 (16)
In1—N12.1095 (8)C18—H180.979 (14)
In1—N22.1213 (9)C18—C191.4148 (15)
In1—N32.1127 (9)C20—H20a0.991 (14)
In1—N42.3656 (9)C20—H20b1.003 (13)
P1—C71.8634 (12)C21—H210.977 (14)
P1—C81.8716 (11)C21—C231.5272 (18)
P1—C91.8657 (11)C21—C241.5333 (17)
P2—C201.8723 (11)C22—H220.979 (14)
P2—C211.8596 (11)C22—C251.5317 (18)
P2—C221.8795 (11)C22—C261.5321 (16)
P3—C331.8900 (11)C23—H23a0.989 (14)
P3—C341.8662 (11)C23—H23b0.963 (14)
P3—C351.8547 (11)C23—H23c0.977 (14)
N1—C61.3680 (15)C24—H24a0.946 (14)
N1—C71.4454 (15)C24—H24b0.927 (14)
N2—C191.3675 (13)C24—H24c0.954 (14)
N2—C201.4479 (14)C25—H25a0.970 (14)
N3—C321.3711 (13)C25—H25b0.967 (13)
N3—C331.4428 (13)C25—H25c0.938 (14)
N4—C11.4663 (13)C26—H26a0.983 (14)
N4—C141.4597 (13)C26—H26b0.954 (14)
N4—C271.4646 (13)C26—H26c0.916 (14)
C1—C21.3864 (15)C27—C281.3844 (14)
C1—C61.4286 (15)C27—C321.4266 (14)
C2—H20.955 (14)C28—H281.004 (14)
C2—C31.3995 (16)C28—C291.3967 (16)
C3—H30.908 (14)C29—H290.897 (14)
C3—C41.3923 (17)C29—C301.3868 (17)
C4—H40.978 (14)C30—H300.930 (14)
C4—C51.3899 (15)C30—C311.3913 (16)
C5—H50.954 (14)C31—H310.955 (14)
C5—C61.4117 (15)C31—C321.4078 (14)
C7—H7a0.951 (14)C33—H33a0.990 (13)
C7—H7b0.995 (15)C33—H33b0.966 (12)
C8—H80.970 (15)C34—H340.959 (14)
C8—C101.5350 (18)C34—C361.5327 (16)
C8—C111.5315 (18)C34—C371.5322 (16)
C9—H90.994 (14)C35—H350.955 (14)
C9—C121.5320 (17)C35—C381.5346 (17)
C9—C131.5277 (17)C35—C391.5302 (17)
C10—H10a1.007 (14)C36—H36a0.923 (14)
C10—H10b0.967 (14)C36—H36b0.985 (14)
C10—H10c1.007 (14)C36—H36c1.045 (14)
C11—H11a0.932 (14)C37—H37a0.988 (15)
C11—H11b0.939 (14)C37—H37b0.960 (14)
C11—H11c0.997 (14)C37—H37c0.923 (15)
C12—H12a0.957 (14)C38—H38a0.928 (15)
C12—H12b1.025 (14)C38—H38b0.920 (14)
C12—H12c0.948 (15)C38—H38c0.998 (14)
C13—H13a0.936 (15)C39—H39a0.942 (15)
C13—H13b0.974 (15)C39—H39b0.938 (14)
C13—H13c0.953 (15)C39—H39c1.032 (15)
C14—C151.3862 (14)
Hb—Ni1—Ha33.3 (6)C15—C14—N4121.33 (9)
In1—Ni1—Ha162.5 (5)C19—C14—N4117.86 (8)
In1—Ni1—Hb161.2 (5)C19—C14—C15120.79 (9)
P1—Ni1—Ha91.2 (5)H15—C15—C14120.4 (9)
P1—Ni1—Hb92.0 (5)C16—C15—C14121.36 (10)
P1—Ni1—In181.122 (8)C16—C15—H15117.9 (9)
P2—Ni1—Ha88.7 (5)H16—C16—C15121.9 (8)
P2—Ni1—Hb115.8 (5)C17—C16—C15118.63 (10)
P2—Ni1—In182.393 (8)C17—C16—H16119.5 (8)
P2—Ni1—P1122.758 (11)H17—C17—C16120.3 (8)
P3—Ni1—Ha112.8 (5)C18—C17—C16121.08 (10)
P3—Ni1—Hb83.9 (5)C18—C17—H17118.6 (8)
P3—Ni1—In184.558 (8)H18—C18—C17118.8 (8)
P3—Ni1—P1120.195 (12)C19—C18—C17121.43 (10)
P3—Ni1—P2112.158 (12)C19—C18—H18119.7 (8)
Hb—Ha—Ni171.7 (13)C14—C19—N2118.78 (9)
Ha—Hb—Ni174.9 (13)C18—C19—N2124.50 (10)
N1—In1—Ni1104.66 (3)C18—C19—C14116.71 (9)
N2—In1—Ni1102.76 (2)N2—C20—P2108.24 (7)
N2—In1—N1116.48 (4)H20a—C20—P2107.7 (8)
N3—In1—Ni1103.32 (2)H20a—C20—N2115.6 (8)
N3—In1—N1111.74 (3)H20b—C20—P2108.7 (8)
N3—In1—N2115.78 (4)H20b—C20—N2112.6 (9)
N4—In1—Ni1178.62 (2)H20b—C20—H20a103.6 (11)
N4—In1—N176.60 (4)H21—C21—P2107.0 (8)
N4—In1—N276.09 (3)C23—C21—P2112.34 (8)
N4—In1—N376.63 (3)C23—C21—H21108.1 (9)
C7—P1—Ni1117.47 (4)C24—C21—P2110.02 (8)
C8—P1—Ni1110.54 (4)C24—C21—H21109.2 (8)
C8—P1—C7103.31 (5)C24—C21—C23110.09 (10)
C9—P1—Ni1116.56 (4)H22—C22—P2104.3 (8)
C9—P1—C7102.11 (5)C25—C22—P2110.95 (7)
C9—P1—C8105.35 (5)C25—C22—H22108.7 (8)
C20—P2—Ni1118.02 (4)C26—C22—P2115.81 (8)
C21—P2—Ni1114.45 (4)C26—C22—H22107.8 (9)
C21—P2—C20102.55 (5)C26—C22—C25109.00 (9)
C22—P2—Ni1117.38 (4)H23a—C23—C21110.1 (8)
C22—P2—C20100.49 (5)H23b—C23—C21110.9 (9)
C22—P2—C21101.39 (5)H23b—C23—H23a107.1 (12)
C33—P3—Ni1118.86 (3)H23c—C23—C21110.0 (9)
C34—P3—Ni1112.80 (4)H23c—C23—H23a108.4 (12)
C34—P3—C3399.02 (5)H23c—C23—H23b110.2 (12)
C35—P3—Ni1118.80 (4)H24a—C24—C21113.3 (9)
C35—P3—C3399.65 (5)H24b—C24—C21108.9 (9)
C35—P3—C34104.94 (5)H24b—C24—H24a110.7 (13)
C6—N1—In1113.05 (7)H24c—C24—C21112.1 (9)
C7—N1—In1115.68 (7)H24c—C24—H24a106.9 (12)
C7—N1—C6119.35 (8)H24c—C24—H24b104.5 (12)
C19—N2—In1113.06 (7)H25a—C25—C22111.1 (8)
C20—N2—In1118.07 (7)H25b—C25—C22115.0 (8)
C20—N2—C19120.53 (9)H25b—C25—H25a109.0 (11)
C32—N3—In1113.26 (7)H25c—C25—C22109.9 (9)
C33—N3—In1118.74 (6)H25c—C25—H25a106.7 (12)
C33—N3—C32119.49 (9)H25c—C25—H25b104.8 (12)
C1—N4—In1103.25 (6)H26a—C26—C22108.0 (8)
C14—N4—In1103.48 (6)H26b—C26—C22111.0 (9)
C14—N4—C1115.79 (8)H26b—C26—H26a109.7 (12)
C27—N4—In1102.76 (6)H26c—C26—C22113.1 (9)
C27—N4—C1113.41 (8)H26c—C26—H26a105.4 (12)
C27—N4—C14115.70 (8)H26c—C26—H26b109.5 (12)
C2—C1—N4121.42 (9)C28—C27—N4121.25 (9)
C6—C1—N4117.90 (9)C32—C27—N4117.83 (8)
C6—C1—C2120.61 (9)C32—C27—C28120.92 (9)
H2—C2—C1120.6 (9)H28—C28—C27118.8 (8)
C3—C2—C1121.34 (10)C29—C28—C27121.22 (10)
C3—C2—H2118.0 (9)C29—C28—H28119.9 (8)
H3—C3—C2123.4 (9)H29—C29—C28119.4 (9)
C4—C3—C2118.71 (10)C30—C29—C28118.50 (10)
C4—C3—H3117.9 (9)C30—C29—H29122.1 (9)
H4—C4—C3117.6 (8)H30—C30—C29121.6 (9)
C5—C4—C3120.75 (10)C31—C30—C29121.11 (10)
C5—C4—H4121.7 (8)C31—C30—H30117.3 (9)
H5—C5—C4120.7 (9)H31—C31—C30119.4 (8)
C6—C5—C4121.62 (10)C32—C31—C30121.44 (10)
C6—C5—H5117.6 (9)C32—C31—H31119.1 (8)
C1—C6—N1119.04 (10)C27—C32—N3119.25 (9)
C5—C6—N1123.98 (10)C31—C32—N3124.04 (9)
C5—C6—C1116.97 (10)C31—C32—C27116.71 (9)
N1—C7—P1108.62 (8)N3—C33—P3111.55 (7)
H7a—C7—P1108.3 (8)H33a—C33—P3105.5 (9)
H7a—C7—N1114.8 (8)H33a—C33—N3112.8 (9)
H7b—C7—P1109.9 (8)H33b—C33—P3107.2 (9)
H7b—C7—N1110.9 (8)H33b—C33—N3114.0 (8)
H7b—C7—H7a104.1 (12)H33b—C33—H33a105.3 (11)
H8—C8—P1101.8 (9)H34—C34—P3104.6 (9)
C10—C8—P1117.04 (9)C36—C34—P3114.77 (8)
C10—C8—H8106.8 (9)C36—C34—H34107.8 (9)
C11—C8—P1110.40 (9)C37—C34—P3113.40 (8)
C11—C8—H8108.6 (9)C37—C34—H34104.9 (9)
C11—C8—C10111.38 (11)C37—C34—C36110.59 (9)
H9—C9—P1104.6 (8)H35—C35—P3105.2 (9)
C12—C9—P1109.97 (8)C38—C35—P3108.61 (8)
C12—C9—H9109.6 (8)C38—C35—H35107.8 (9)
C13—C9—P1116.61 (9)C39—C35—P3113.41 (8)
C13—C9—H9106.9 (8)C39—C35—H35109.8 (9)
C13—C9—C12108.90 (11)C39—C35—C38111.66 (10)
H10a—C10—C8115.6 (8)H36a—C36—C34111.5 (9)
H10b—C10—C8112.3 (8)H36b—C36—C34108.8 (8)
H10b—C10—H10a105.3 (12)H36b—C36—H36a110.2 (12)
H10c—C10—C8107.7 (8)H36c—C36—C34110.7 (8)
H10c—C10—H10a108.0 (12)H36c—C36—H36a108.4 (12)
H10c—C10—H10b107.7 (12)H36c—C36—H36b107.3 (11)
H11a—C11—C8108.8 (9)H37a—C37—C34107.0 (9)
H11b—C11—C8110.9 (9)H37b—C37—C34112.4 (9)
H11b—C11—H11a106.5 (13)H37b—C37—H37a108.5 (12)
H11c—C11—C8112.2 (8)H37c—C37—C34109.4 (9)
H11c—C11—H11a109.0 (12)H37c—C37—H37a110.3 (12)
H11c—C11—H11b109.2 (12)H37c—C37—H37b109.3 (13)
H12a—C12—C9109.4 (9)H38a—C38—C35110.9 (9)
H12b—C12—C9111.5 (8)H38b—C38—C35111.6 (9)
H12b—C12—H12a107.0 (12)H38b—C38—H38a106.5 (13)
H12c—C12—C9108.3 (9)H38c—C38—C35110.9 (8)
H12c—C12—H12a109.1 (12)H38c—C38—H38a108.6 (12)
H12c—C12—H12b111.5 (11)H38c—C38—H38b108.1 (12)
H13a—C13—C9109.1 (9)H39a—C39—C35112.7 (9)
H13b—C13—C9110.7 (8)H39b—C39—C35112.2 (9)
H13b—C13—H13a109.7 (12)H39b—C39—H39a108.3 (12)
H13c—C13—C9112.9 (9)H39c—C39—C35111.5 (8)
H13c—C13—H13a110.2 (12)H39c—C39—H39a106.5 (12)
H13c—C13—H13b104.2 (12)H39c—C39—H39b105.3 (12)
In1—N1—C6—C126.77 (8)N2—C19—C18—C17179.43 (11)
In1—N1—C6—C5152.23 (7)N3—C32—C27—N44.06 (12)
In1—N1—C7—P129.39 (5)N3—C32—C27—C28176.42 (10)
In1—N2—C19—C1426.58 (8)N3—C32—C31—C30178.51 (12)
In1—N2—C19—C18152.09 (7)N4—C1—C2—C3177.45 (10)
In1—N2—C20—P223.17 (6)N4—C1—C6—C5176.91 (9)
In1—N3—C32—C2722.34 (8)N4—C14—C15—C16178.43 (10)
In1—N3—C32—C31157.41 (8)N4—C14—C19—C18177.81 (9)
In1—N3—C33—P314.25 (6)N4—C27—C28—C29176.60 (11)
In1—N4—C1—C2157.28 (6)N4—C27—C32—C31176.17 (10)
In1—N4—C1—C619.53 (7)C1—C2—C3—C41.10 (13)
In1—N4—C14—C15157.05 (6)C1—C6—C5—C40.20 (12)
In1—N4—C14—C1921.06 (7)C2—C3—C4—C50.82 (13)
In1—N4—C27—C28156.60 (7)C3—C4—C5—C60.18 (13)
In1—N4—C27—C3223.89 (7)C14—C15—C16—C170.64 (13)
P1—C7—N1—C6169.64 (7)C14—C19—C18—C170.73 (12)
P2—C20—N2—C19169.26 (7)C15—C16—C17—C180.22 (14)
P3—C33—N3—C32160.10 (7)C16—C17—C18—C190.48 (15)
N1—C6—C1—N42.16 (11)C27—C28—C29—C300.21 (15)
N1—C6—C1—C2179.00 (10)C27—C32—C31—C301.25 (13)
N1—C6—C5—C4179.22 (11)C28—C29—C30—C311.91 (16)
N2—C19—C14—N40.97 (11)C29—C30—C31—C321.36 (16)
N2—C19—C14—C15179.08 (10)
(GOJNIF_IAM_NoMoRe) top
Crystal data top
C39H62InN4NiP3Dx = 1.415 Mg m3
Mr = 853.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9537 reflections
a = 12.2127 (4) Åθ = 2.3–36.4°
b = 14.5402 (5) ŵ = 1.20 mm1
c = 22.5601 (8) ÅT = 100 K
V = 4006.1 (2) Å3Block, gold
Z = 40.14 × 0.08 × 0.06 mm
F(000) = 1784.150
Data collection top
Bruker Photon-II CMOS
diffractometer
18741 reflections with I 2u(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
SADABS. R.Blessing, 1995
θmax = 36.4°, θmin = 2.3°
Tmin = 0.701, Tmax = 0.747h = 2020
237431 measured reflectionsk = 2424
19473 independent reflectionsl = 3737
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullOnly H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.018 w = 1/[σ2(Fo2) + (0.0167P)2 + 1.352P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.042(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.43 e Å3
19473 reflectionsΔρmin = 0.51 e Å3
619 parametersAbsolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881.
0 restraintsAbsolute structure parameter: 0.003 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.755800 (10)0.598649 (8)0.856160 (6)0.00937 (2)
H1A0.7243 (18)0.5783 (15)0.9261 (9)0.036333
H1B0.756 (2)0.6348 (14)0.9218 (9)0.035000
In10.798245 (5)0.580830 (4)0.749321 (3)0.008364 (12)
P10.91844 (2)0.522268 (17)0.864329 (11)0.00941 (4)
P20.59906 (2)0.528573 (18)0.829180 (11)0.00948 (4)
P30.75362 (2)0.750099 (17)0.835687 (11)0.00922 (4)
N10.96165 (6)0.53377 (5)0.74728 (4)0.01070 (12)
N20.67671 (7)0.48677 (6)0.72033 (4)0.01115 (14)
N3