Home Physical Sciences Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12
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Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12

  • Kiyoshi Fujisawa ORCID logo EMAIL logo , Moemi Okamura and Edward R. T. Tiekink ORCID logo EMAIL logo
Published/Copyright: November 17, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 1

Abstract

C30H44B2CuN12, triclinic, P 1 ‾ (no. 2), a = 8.6801(1) Å, b = 10.1688(2) Å, c = 10.7290(2) Å, α = 62.672(2)°, β = 84.3550(10)°, γ = 78.9700(10)°, V = 825.71(3) Å3, Z = 1, R gt (F) = 0.0318, wR ref (F 2) = 0.0961, T = 178 K.

CCDC no.: 2118551

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Blue prism
Size: 0.17 × 0.15 × 0.03 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.70 mm−1
Diffractometer, scan mode: Rigaku XtaLAB P200, ω
θ max, completeness: 29.8°, >99%
N(hkl)measured, N(hkl)unique, R int: 27,784, 4444, 0.029
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 4288
N(param)refined: 211
Programs: CrysAlisPRO [1], SIR2014 [2], SHELX [3], WinGX/ORTEP [4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
Cu 0.5 0.0 0.0 0.02311 (8)
N11 0.33323 (12) 0.13068 (11) 0.05647 (10) 0.0253 (2)
N12 0.26240 (12) 0.06437 (11) 0.18590 (10) 0.02460 (19)
N21 0.33535 (15) −0.18292 (13) 0.10693 (12) 0.0341 (2)
N22 0.29741 (13) −0.21090 (12) 0.24250 (11) 0.0294 (2)
N31 0.59981 (12) −0.07955 (12) 0.19672 (11) 0.0283 (2)
N32 0.50163 (12) −0.11339 (11) 0.31202 (11) 0.0270 (2)
C1 0.3007 (2) 0.38129 (16) −0.15342 (15) 0.0423 (3)
H1A 0.372813 0.327324 −0.197144 0.063*
H1B 0.350881 0.458072 −0.150016 0.063*
H1C 0.204608 0.429309 −0.208628 0.063*
C2 0.26060 (16) 0.27329 (14) −0.00778 (13) 0.0311 (3)
C3 0.14323 (18) 0.29895 (15) 0.08067 (15) 0.0365 (3)
H3 0.074381 0.390549 0.061542 0.044*
C4 0.14663 (15) 0.16573 (15) 0.20102 (13) 0.0300 (2)
C5 0.04264 (19) 0.13038 (19) 0.32779 (16) 0.0411 (3)
H5A −0.024877 0.060968 0.333001 0.062*
H5B −0.022640 0.223152 0.321545 0.062*
H5C 0.107154 0.083814 0.412066 0.062*
C6 0.3280 (3) −0.3044 (2) −0.0445 (2) 0.0563 (5)
H6A 0.227680 −0.274389 −0.092734 0.085*
H6B 0.373402 −0.406957 −0.027818 0.085*
H6C 0.400202 −0.235867 −0.102880 0.085*
C7 0.30140 (19) −0.29826 (17) 0.09246 (18) 0.0415 (3)
C8 0.2450 (2) −0.40158 (17) 0.2190 (2) 0.0471 (4)
H8 0.213570 −0.493283 0.237044 0.057*
C9 0.24417 (18) −0.34353 (15) 0.31214 (17) 0.0390 (3)
C10 0.1980 (3) −0.4069 (2) 0.4638 (2) 0.0590 (5)
H10A 0.287533 −0.419705 0.519670 0.088*
H10B 0.165917 −0.504398 0.493623 0.088*
H10C 0.110358 −0.338098 0.477757 0.088*
C11 0.88668 (17) −0.0853 (2) 0.14792 (18) 0.0433 (3)
H11A 0.937875 −0.181575 0.151466 0.065*
H11B 0.960456 −0.044066 0.178246 0.065*
H11C 0.853973 −0.015059 0.051646 0.065*
C12 0.74626 (16) −0.10832 (15) 0.24292 (15) 0.0338 (3)
C13 0.74209 (17) −0.16084 (17) 0.38809 (16) 0.0388 (3)
H13 0.829419 −0.189445 0.447220 0.047*
C14 0.58605 (17) −0.16321 (15) 0.42930 (14) 0.0330 (3)
C15 0.5142 (2) −0.2093 (2) 0.57286 (15) 0.0456 (4)
H15A 0.428982 −0.129921 0.571193 0.068*
H15B 0.594323 −0.225928 0.639203 0.068*
H15C 0.472382 −0.302272 0.602181 0.068*
B1 0.32444 (16) −0.09898 (15) 0.29440 (14) 0.0258 (2)
H1 0.264735 −0.123218 0.393853 0.031*

Source of material

A mixed solvent system comprising acetone (20 mL) and dichloromethane (20 mL) was added to a mixture of K{HB(3,5-Me2pz)3} (369 mg, 1.097 mmol) [5] and Cu(NO3)2·3H2O (150 mg, 0.621 mmol). After the mixture was stirred for 30 min, the solvent was evaporated under vacuum. The resulting solid was washed with distilled water (10 mL) to remove side-products, e.g. KNO3. Pale-blue crystals were obtained by the crystallisation of the remaining solid from a dichloromethane/hexane (10 mL/5 mL) solution at −30 °C. Yield: 34% (121 mg, 0.184 mmol). Anal. Calcd. for C30H44B2CuN12(H2O). C; 53.31, H; 6.86, N; 24.87%. Found: C; 53.08, H; 6.62, N; 24.87%. IR (JASCO FT/IR-550 spectrophotometer, KBr; cm−1): 2925 (s) ν(C–H), 2506 (s) ν(B–H), 1541 (s) ν(C=N). Far-IR (JASCO FT/IR-6700 spectrophotometer, CsI; cm−1): 649 (s), 471 (s), 277 (s) ν(Cu–N). UV–Vis (JASCO V-570 at 298 K) in dichloromethane: λ max/nm (ε, mol−1 L cm−1) 313 (800), 645 (24). ESR (JEOL JES-RE2X, 5 mm φ quartz tube, dichloromethane, 143 K): g ‖ , 2.22 ( A ‖ , 154 G); g(⊥), 2.07.

Experimental details

The C- and B-bound H atoms were geometrically placed (C–H = 0.95–1.00 Å & B–H = 1.12 Å) and refined as riding with U iso(H) = 1.2–1.5U eq(C) and 1.2U eq(B). Owing to poor agreement, two reflections, i.e. (0 0 1) and (3 1 1), were omitted from the final cycles of refinement.

Comment

Since their earliest reports, poly(1-pyrazolyl)borates have been established as an important class of ligands in contemporary coordination chemistry [5]. Among these ligands, the methyl substituted mono-anion, hydridotris{(3,5-dimethylpyrazolyl-1-yl)borato-κN 3} anion, denoted as HB{(3,5-Me2pz)3}, is prototypical of the substituted derivatives [5], [6], [7]. This ligand is relatively sterically unhindered so it can readily form coordinatively saturated six-coordinate complexes, formulated as [M{HB(3,5-Me2pz)3}2]. The crystal structure of the copper(II) derivative [Cu{HB(3,5-Me2pz)3}2], has been described previously [8] but was experimentally flawed and subsequently was subjected to a space group change [9]. However, the derived Cu–N bond lengths, being close to equivalent, do not match expectation; another room temperature determination exhibits relatively high standard uncertainty values on derived parameters [10]. Hence, it was thought worthwhile to redetermine this benchmark structure at reduced temperature in order to reliably determine the crucial intramolecular parameters; new spectroscopic data are also presented.

The molecular structure of [Cu{HB(3,5-Me2pz)3}2] is shown in the figure (35% displacement ellipsoids). The copper(II) centre lies on a centre of inversion being coordinated by the six nitrogen atoms derived from two symmetry related tripodal {HB(3,5-Me2pz)3}− anions. The Cu–N bond lengths span a range of 0.34 Å with the shortest Cu–N11 bond being 2.0147(10) Å compared to the longest bond of 2.3567(12) for Cu–N21; at 2.0936(11) Å, the Cu–N31 bond length is intermediate between these extremes. These observations suggest a significant deviation from putative three-fold symmetry along the HB⃛Cu axis, being consistent with an elongated rhombic octahedral geometry. Further, the sequence of dihedral angles between the N11-/N21, N11-/N31- and N21-/N31-pyrazolyl rings is 54.95(9), 58.55(9) and 69.60(10)°, respectively. The d9 electronic configuration of the copper(II) ion gives three electrons in the doubly degenerate eg orbitals, therefore the relative elongation of the Cu1–N21 bond is traced to the Jahn–Teller distortion, an effect which lowers the electrostatic repulsion between the electron-pairs on the Lewis basic pyrazole ligands, with the result the overall energy of the complex decreases [11].

The elongated rhombic octahedral structure just described was not observed in other metal(II) complexes of comparable formulation: [M{HB(3,5-Me2pz)3}2] for M = Fe [12], M = Co [13] and M = Zn [14], forming instead close to regular octahedral coordination geometries.

In the far-IR spectrum, the strong peak at 277 cm−1 can be assigned as ν(Cu–N). This observation is consistent with ν(Fe–N), which was assigned by far-IR spectroscopy at 192 cm−1 and NRSV (nuclear resonance vibrational spectroscopy) at 197 cm−1 [15]. The ground state of the title complex is dx2-y2, which was observed in its ESR spectrum with its ESR parameter g ‖ being 2.22 ( A ‖ , 154 G) [11]. This ground state also support by UV–Vis spectroscopy as the d–d transition occurs at 645 nm (24 mol−1 cm−1 L), which is shifted by 85 nm to higher energy compared with that of 730 nm (100−1 cm−1 L) observed for the recently reported complex [Cu(Cl)(3,5-Me2pzH){HB(3,5-Me2pz)3}] [16]. This difference arises from the different coordination geometries: elongated rhombic octahedral and distorted square pyramidal geometries, respectively.

An analysis of the molecular packing employing PLATON [17] suggests the absence of directional interactions between molecules. This analysis was complemented by the calculation, using Crystal Explorer 17 [18], of the Hirshfeld surfaces and of the full and delineated two-dimensional fingerprint plots conducted employing literature protocols [19]. These calculations show that H⃛H contacts contribute 85.7% to the calculated surface with the only other contacts of note being C⃛H/H⃛C [11.5%] and N⃛H/H⃛N [2.9%].

Corresponding authors: Kiyoshi Fujisawa, Department of Chemistry, Ibaraki University, Mito, Ibaraki 310-8512, Japan, Email: ; and Edward R. T. Tiekink, Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia, E-mail:

Funding source: Sunway University

Award Identifier / Grant number: GRTIN-IRG-01-2021

Acknowledgements

KF is grateful for support from the joint usage/research programme “Artificial Photosynthesis” based at Osaka City University.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This study was financially supported by Sunway University Sdn Bhd No. GRTIN-IRG-01-2021.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2021-10-13
Accepted: 2021-10-29
Published Online: 2021-11-17
Published in Print: 2022-02-23

© 2021 Kiyoshi Fujisawa et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  43. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)zinc(II)], C64H44Br4N8O8Zn2
  44. The crystal structure of catena-poly[(1-(4-carboxybenzyl)pyridin-1-ium-4-carboxylato-κ1O)-(μ2-oxalato-κ4 O:O′:O″:O‴)dioxidouranium(VI)], C16H11NO10U
  45. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
  46. Halogen bonds in the crystal structure of 4,3′:5′,4″-terpyridine — 1,3-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  47. Crystal structure of 2-(1H-indol-3-yl)ethan-1-aminium 2-(4-acetylphenoxy)acetate, C20H22N2O4
  48. Chalcogen bonds in the crystal structure of 4,7-dibromo-2,1,3-benzoselenadiazole, C6H2Br2N2Se
  49. The crystal structure of 1,4-bis((1H-benzimidazol-2-yl)methyl)-piperazine-2,5-dione dihydrate, C20H22N6O4
  50. The crystal structure of C19H20O8
  51. The crystal structure of KNa3Te8O18·5H2O exhibiting a ∞2[Te4O9]2− layer
  52. Erratum
  53. Erratum to: Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
https://doi.org/10.1515/ncrs-2021-0396
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-3-yl)methylene)-3, 4-dihydronaphthalen-1(2H)-one, C17H15NO3
  4. Crystal structure of (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1 (2H)-one, C18H17NO3
  5. The crystal structure of N 6,N 6′-di(pyridin-2-yl)-[2,2′-bipyridine]-6,6′-diamine, C20H16N6
  6. The crystal structure of {N 1,N 2-bis[2,4-dimethyl-6-(4-(tert-butyl)phenyl)(phenyl)methyl]acenaphthylene-1,2-diimino-κ2 N, N′}-dibromido-nickel(II) – dichloromethane(1/2), C64H64Br2Cl4N2Ni
  7. Synthesis and crystal structure of nonacarbonyltris[(2-thia-1,3,5-triaza-7-phosphatricylco[3.3.1.1]decane-κ1 P)-2,2-dioxide]triruthenium(0) – acetonitrile (7/6), C25.71H32.57N9.86O15P3S3Ru3
  8. A new polymorph of 1-(4-nitrophenyl)-1H-benzimidazole (C13H9N3O2)
  9. The crystal structure of 2,2′-((1E,1′E)-(naphthalene-2,3 diylbis(azanylylidene)) bis(methanylylidene))bis(4-methylphenol), C26H22N2O2
  10. The crystal structure of bis(μ2-iodido)-bis(η6-benzene)-bis(iodido)-diosmium(II), C12H12I4Os2
  11. Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12
  12. Crystal structure of (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
  13. Crystal structure of 2,2′-(p-tolylazanediyl)bis(1-phenylethan-1-one), C23H21NO2
  14. Redetermination of the crystal structure of the crystal sponge the poly[tetrakis(μ3-2,4,6-tris(pyridin-4-yl)-1,3,5-triazine)-dodecaiodidohexazinc(II) nitrobenzene solvate], C72H48I12N24Zn6⋅10(C6H5NO2)
  15. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C44H45N5O2
  16. Crystal structure of (E)-7-fluoro-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O1
  17. Crystal structure of tetrabutylammonium sulfanilate – 1-(diaminomethylene)thiourea (1/2)
  18. Crystal structure of [2,2′-{azanediyl)bis[(propane-3,1-diyl)(azanylylidene)methylylidene]} bis(3,5-dichlorophenolato)-κ2O,O′]-isothiocyanato-κN-iron(III), C21H19Cl4FeN4O2S
  19. Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2
  20. Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2
  21. Chlorido-(2,2′-(ethane-bis(5-methoxyphenolato))-κ4 N,N′,O,O′)manganese(III) monohydrate, C19H18Cl2CuN2O2
  22. Crystal structure of 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one, C22H28O2
  23. Crystal structure of [6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato)-κ4N,N′,O,O′]copper(II)
  24. Crystal structure of 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione, C30H20O4N2Cl2S2
  25. Crystal structure of bis{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl)borato-κN 3}manganese(II), C30H26B2F18MnN12
  26. Crystal structure of 1-(2-methylphenyl)-2-(2-methylbenzo[b]thienyl)-3,3,4,4,5,5-hexafluorocyclopent-ene, C21H14F6S
  27. Crystal structure of 2-(3-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  28. Crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium chloride – chloroform (1/1), C21H23Cl4I2N3
  29. Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3
  30. The crystal structure of 2-(4-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  31. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C9H14F12N4P2
  32. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(pyren-1-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C54H48N4O2
  33. Crystal structure of poly[bis(μ2-2,6-bis(1-imidazoly)pyridine-κ2 N,N′)-bis(thiocyanato-κ1 N)copper(II)] dithiocyanate, C24H18CuN12S2
  34. Cones with a three-fold symmetry constructed from three hydrogen bonded theophyllinium cations that coat [FeCl4]− anions in the crystal structure of tris(theophyllinium) bis(tetrachloridoferrate(III)) chloride trihydrate, C21H33Cl9Fe2N12O9
  35. Crystal structure of 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin monohydrate, C32H49N3O6S
  36. The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
  37. The crystal structure of 4-phenyl-4-[2-(pyridine-4-carbonyl)hydrazinylidene]butanoic acid, C16H15N3O3
  38. The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3
  39. Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)
  40. Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene) hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
  41. Crystal structure of (E)-amino(2-((5-methylfuran-2-yl)methylene)hydrazinyl) methaniminium nitrate monohydrate, C14H26N10O10
  42. The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
  43. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)zinc(II)], C64H44Br4N8O8Zn2
  44. The crystal structure of catena-poly[(1-(4-carboxybenzyl)pyridin-1-ium-4-carboxylato-κ1O)-(μ2-oxalato-κ4 O:O′:O″:O‴)dioxidouranium(VI)], C16H11NO10U
  45. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
  46. Halogen bonds in the crystal structure of 4,3′:5′,4″-terpyridine — 1,3-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  47. Crystal structure of 2-(1H-indol-3-yl)ethan-1-aminium 2-(4-acetylphenoxy)acetate, C20H22N2O4
  48. Chalcogen bonds in the crystal structure of 4,7-dibromo-2,1,3-benzoselenadiazole, C6H2Br2N2Se
  49. The crystal structure of 1,4-bis((1H-benzimidazol-2-yl)methyl)-piperazine-2,5-dione dihydrate, C20H22N6O4
  50. The crystal structure of C19H20O8
  51. The crystal structure of KNa3Te8O18·5H2O exhibiting a ∞2[Te4O9]2− layer
  52. Erratum
  53. Erratum to: Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
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