Home Crystal structure of chlorido{hydridotris[3-phenyl-5-methylpyrazol-1-yl-κN3]borato}copper(II), C30H28BClCuN6
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Crystal structure of chlorido{hydridotris[3-phenyl-5-methylpyrazol-1-yl-κN3]borato}copper(II), C30H28BClCuN6

  • Kiyoshi Fujisawa ORCID logo EMAIL logo , Masaya Shimizu and Edward R. T. Tiekink ORCID logo EMAIL logo
Published/Copyright: October 2, 2020

Abstract

C30H28BClCuN6, triclinic, P1 (no. 2), a = 11.549(3) Å, b = 12.321(3) Å, c = 12.348(4) Å, α = 111.785(1)°, β = 116.664(3)°, γ = 97.513(1)°, V = 1361.3(7) Å3, Z = 2, Rgt(F) = 0.0440, wRref(F2) = 0.1063, T = 197 K.

CCDC no: 2027352

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:Red slab
Size0.20 × 0.20 × 0.05 mm
Wavelength:Mo radiation (0.71073 Å)
μ:0.93 mm−1
Diffractometer, scan modeRigaku Mercury70, ω
θmax, completeness:27.5°, 99 %
N(hkl)measured, N(hkl)unique, Rint:11245, 6149, 0.024
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4903
N(param)refined:355
Programs:REQAB [1], CrystalClear [2], SIR2014 [3], SHELX [4], WinGX/ORTEP [5]
Table 2:

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

AtomxyzUiso*/Ueq
Cu0.82167 (3)0.24667 (3)0.61708 (3)0.02796 (10)
Cl10.68003 (7)0.19846 (7)0.67373 (7)0.04129 (18)
N110.8585 (2)0.25491 (19)0.4816 (2)0.0284 (4)
N120.9911 (2)0.32572 (19)0.5349 (2)0.0289 (5)
N210.9821 (2)0.1791 (2)0.6851 (2)0.0297 (5)
N221.0988 (2)0.24965 (19)0.7027 (2)0.0297 (5)
N310.92672 (19)0.43375 (19)0.7398 (2)0.0281 (4)
N321.0636 (2)0.45820 (19)0.7810 (2)0.0284 (4)
C110.7821 (2)0.2237 (2)0.3469 (2)0.0274 (5)
C120.8682 (3)0.2763 (2)0.3141 (3)0.0314 (6)
H120.8418170.2697430.2264870.038*
C130.9983 (3)0.3391 (2)0.4332 (3)0.0299 (5)
C140.6342 (2)0.1456 (2)0.2596 (2)0.0278 (5)
C150.5436 (3)0.1558 (3)0.1458 (3)0.0384 (6)
H150.5773740.2145020.1245640.046*
C160.4044 (3)0.0811 (3)0.0631 (3)0.0462 (7)
H160.3436030.088487−0.0148040.055*
C170.3535 (3)−0.0034 (3)0.0928 (3)0.0434 (7)
H170.257771−0.0540160.0359560.052*
C180.4415 (3)−0.0146 (3)0.2048 (3)0.0404 (7)
H180.406435−0.0729400.2257270.048*
C190.5807 (3)0.0584 (2)0.2872 (3)0.0354 (6)
H190.6408780.0490790.3638090.043*
C201.1312 (3)0.4105 (3)0.4588 (3)0.0389 (6)
H20A1.1657950.4973450.5310470.058*
H20B1.1147940.4089780.3731060.058*
H20C1.1999760.3719370.4889450.058*
C211.0096 (3)0.0827 (2)0.7032 (3)0.0313 (5)
C221.1426 (3)0.0901 (3)0.7303 (3)0.0347 (6)
H221.1872690.0331750.7462220.042*
C231.1959 (2)0.1961 (2)0.7294 (2)0.0316 (5)
C240.9135 (3)−0.0114 (2)0.7008 (3)0.0319 (5)
C250.7719 (3)−0.0630 (3)0.6035 (3)0.0379 (6)
H250.733737−0.0381530.5346570.045*
C260.6852 (3)−0.1506 (3)0.6053 (3)0.0442 (7)
H260.588177−0.1849930.5384450.053*
C270.7405 (3)−0.1875 (3)0.7047 (3)0.0481 (8)
H270.681462−0.2476290.7061240.058*
C280.8809 (3)−0.1375 (3)0.8015 (3)0.0478 (7)
H280.918698−0.1637250.8691250.057*
C290.9673 (3)−0.0491 (3)0.8006 (3)0.0415 (7)
H291.064036−0.0139400.8686880.050*
C301.3350 (3)0.2512 (3)0.7552 (3)0.0419 (7)
H30A1.3229540.2565750.6737990.063*
H30B1.3892400.1979650.7727730.063*
H30C1.3840530.3352060.8360180.063*
C310.9219 (2)0.5303 (2)0.8329 (2)0.0287 (5)
C321.0568 (3)0.6166 (2)0.9363 (3)0.0338 (6)
H321.0834000.6931291.0149020.041*
C331.1430 (3)0.5676 (2)0.9007 (3)0.0320 (6)
C340.7886 (3)0.5402 (2)0.8124 (3)0.0288 (5)
C350.6679 (3)0.4770 (2)0.6810 (3)0.0323 (6)
H350.6713250.4260020.6037320.039*
C360.5429 (3)0.4871 (3)0.6611 (3)0.0383 (6)
H360.4610340.4429740.5707700.046*
C370.5375 (3)0.5615 (3)0.7727 (3)0.0451 (7)
H370.4516900.5682590.7597590.054*
C380.6564 (3)0.6259 (3)0.9026 (3)0.0486 (8)
H380.6526190.6784770.9790360.058*
C390.7817 (3)0.6155 (3)0.9242 (3)0.0378 (6)
H390.8629450.6597221.0149220.045*
C401.2977 (3)0.6183 (3)0.9764 (3)0.0422 (7)
H40A1.3358590.5674381.0181130.063*
H40B1.3333800.7050321.0493120.063*
H40C1.3252890.6156470.9113590.063*
B11.1019 (3)0.3679 (3)0.6867 (3)0.0312 (6)
H11.1956440.4113770.7096400.037*

Source of material

A solution of [Tl{HB(3-Ph-5-Mepz)3}] (300.5 mg, 0.437 mmol) [6] in dichloromethane (20 mL) was added slowly to a solution of CuCl2⋅2H2O (82.1 mg, 0.482 mmol) in acetone (10 mL). After the mixture was stirred for 1 h, the solvent was evaporated under vacuum, and the resulting solid was extracted with dichloromethane (30 mL). The filtrate was evaporated under vacuum, and a brown powder was obtained. Red crystals were obtained by the slow evaporation of a saturated dichloromethane/n-heptane solution held at room temperature. The second crop was contaminated by other adducts involving free pyrazole and/or coordinating solvents. Yield: 28% (72.5 mg, 0.124 mmol).

Anal. Calcd. for C30H28BClCuN6. C, 61.87; H, 4.85; N, 14.43%. Found: C; 61.80, H; 4.70, N; 14.10.

IR (JASCO FT/IR-6300 spectrophotometer, KBr; cm−1): 3058 (w) ν(C–H), 2927 (w) ν(C–H), 2535 (m) ν(B–H), 1542 (s) ν(C=N).

UV–Vis (JASCO V–570 at 298 K); λmax, nm (ε, M–1 cm–1): 369 (1660), 408 (sh, 1510), 520 (sh, 390), 906 (180).

Experimental details

The C- and B-bound H atoms were geometrically placed (C–H = 0.95–1.00 Å & B–H = 1.00 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C) and 1.2Ueq(B). Owing to poor agreement, two reflections, i.e. (4 8 4) and (−11 11 3), were manually omitted from the final cycles of refinement.

Discussion

Comment

The coordination chemistry of hydrotris(pyrazolyl)borate ligands has proven to be a very productive area of research. This is mainly because the coordination environment of a metal can be readily controlled by these ligands which also exert a significant influence upon second sphere coordination effects [7], [8]. This control can be moderated by altering the steric profiles of pyrazoles by substitution at the 3- and/or 5-positions of the pyrazolyl ring. By using the less hindered, parent hydridotris(pyrazolyl)borate, the formation of unreactive and coordinatively saturated complexes, [M{HB(3,5-R2pz)3}2] (R = H and Me), were easily obtained [7], [8]. In 1986, bulkier substituents were introduced at the 3-position of the pyrazolyl ring, [HB(3-Rpz)3]- (R = tBu or Ph) [9], which then lead to 3,5-disubstitution by isopropyl and phenyl groups to prevent the formation of the unreactive, bischelate formation [10], [11], [12]. Therefore, these hindered hydridotris(pyrazolyl)borate ligands were given the term ”tetrahedral enforcer” [13]. In copper(II) coordination chemistry, a D2d distorted tetrahedral structure is very important in inorganic and bioinorganic chemistry, since in copper proteins tetrahedral geometries have been reported for copper(II) centres [14]. However, it remains very difficult to obtain tetrahedral copper(II) complexes as pure compounds, since some additional ligands and/or coordinating solvents can be easily coordinated to the copper(II) centre to form five- or six-coordinate species instead. In this connection, the present work reports the X-ray structural characterization and some properties of a four-coordinate copper(II) complex with a phenyl-substituted hydridotris(pyrazolyl)borate, i.e. [Cu(Cl){HB(3-Ph-5-Mepz)3}], (I).

As mentioned above, tetrahedral copper(II) geometries are not common in coordination chemistry. Therefore, to synthesise complexes with this difficult to obtain geometry, a judicious choice of ligand needs to be made. Among these, the N3-type hydridotris(pyrazolyl)borate ligands are good candidates. By using sterically hindered hydridotris(pyrazolyl)borate ligands, tetrahedral copper(II) complexes have been obtained previously, such as [Cu(Cl){HB(3,5-iPr2pz)3}] [15], [Cu(SC6F5){HB(3,5-iPr2pz)3}] [16], [Cu(OOC(CH3)2C6H5){HB(3,5-iPr2pz)3}] [17], [Cu(OH){HB(3-tBu-5-iPrpz)3}] [18], [Cu(Cl){HB(3-tBu-5-iPrpz)3}] [19], [Cu(Cl){HB(3-Ad-5-iPrpz)3}] [19] and [Cu(Cl){HB(3-tBu-5-Mepz)3}] [20]. However, these complexes with a tetrahedral geometry were quite unstable with ligands such as [HB(3,5-iPr2pz)3]-, i.e. with reduced steric hindrance. Indeed, the addition of small amount of a coordinating solvent such as DMF into a CH2Cl2 solution of [Cu(Cl){HB(3,5-iPr2pz)3}] results in the immediate formation of the solvent adduct, [Cu(Cl)(dmf){HB(3,5-iPr2pz)3}], which was characterized by X-ray diffraction [15]. For the preparation of coordinatively unsaturated [Cu(Cl){HB(3-Ph-5-Mepz)3}], care must be made to avoid contamination by solvent and other species. Therefore, in the present study, the thallium(I) salt [Tl{HB(3-Ph-5-Mepz)3}] [6] was employed. However, the yield was very low (28%), partly because the second crop of crystals was green, consistent with the formation of five-coordinate products.

The molecular structure of (I) is shown in the figure (35% probably displacement ellipsoids). The Cu–Cl bond length in (I) is 2.1446(7) Å, which lies in the range for Cu–Cl bonds in other tetrahedral chlorido copper(II) complexes with pz ligands, viz. [Cu(Cl){HB(3,5-iPr2pz)3}] (2.125(6) Å) [15], [Cu(Cl){HB(3-tBu-5-iPrpz)3}] (2.167(1) Å) [19], [Cu(Cl){HB(3–Ad-5-iPrpz)3}] (2.1706(9) Å) [19] and [Cu(Cl){HB(3-tBu-5-Mepz)3}] (2.1738(14) and 2.1760(13) Å, for the two independent molecules) [20]. On the other hand, examples of Cu–Cl bond lengths in five-coordinate chlorido complexes are 2.260(2) Å in [Cu(Cl)(dmf){HB(3,5-iPr2pz)3}] [15] and 2.2833(8) Å in [Cu(Cl){HB(3-Ph-5-Mepz)3}(3-Ph-5-MepzH)] [21], which represent approximately 0.1 Å elongations compared with the Cu–Cl distances in the four coordinate, chlorido copper(II) percursor complexes. These parameters are comparable with those found in tetrachloridocuprates [14]. This dramatic change is due to differences in the ground state electronic configurations, which change from dz2 to dx2−y2. This change can also be observed in the d–d transition energies: 906 nm (180 M−1 cm−1) in [Cu(Cl){HB(3-Ph-5-Mepz)3}], 996 nm (150 M−1 cm−1) in [Cu(Cl){HB(3,5-iPr2pz)3}] and 758 nm (100 M−1 cm−1) in [Cu(Cl)(dmf){HB(3,5-iPr2pz)3}] [15].

The Cu–N bond lengths in (I) are experimentally distinct with Cu–N11 [1.9348(19) Å] being significantly shorter than Cu–N21 [2.088(2) Å] and Cu–N31 [2.027(2) Å]. The range of tetrahedral angles is broad, i.e. from a narrow 89.02(8)° for N11–Cu–N31 to a wide 150.98(6)° for N11–Cu–Cl1, indicating the N11 atom is approximately trans to the Cl1 atom, which accounts for the disparity in the Cu–N bonds, and a significant deviation from molecular three-fold symmetry.

In the crystal, a prominent intermolecular contact is a phenyl–C–H⃛Cl [C18–H18⃛Cl1i: H18⃛Cl1i = 2.66 Å, C18⃛Cl1i = 3.596(4) Å with angle at H18 = 169°; symmetry operation (i) 1−x, −y, 1−z] interaction between centrosymmetrically related molecules which leads to the formation of a two-molecule aggregate. The only other identified contacts are methyl–C–H⃛π(pyrazolyl) [C20–H20a⃛Cg(N11,N12,C11–C13)ii: H20a⃛Cg(N11,N12,C11–C13)ii = 2.82 Å with angle at H20a = 141° and C20–H20b⃛Cg(N31,N32,C31–C33)ii: H20b⃛Cg(N31,N32,C31–C33)ii = 2.89 Å with angle at H20b = 148° for (ii) 2−x, 1−y, 1−z] interactions, which connect the dimeric aggregates into a supramolecular layer in the ab-plane; layers stack without directional interactions between them.

An analysis of the supramolecular association in the crystal of (I) was also performed by calculating the Hirshfeld surface as well as the full and delineated two-dimensional fingerprint plots employing Crystal Explorer 17 [22] and literature methods [23]. The specified H⃛Cl contacts leading to the dimeric aggregates appear as sharp spikes in the fingerprint plot delineated into H⃛Cl/Cl⃛H contacts; overall, these contribute 8.0% of all contacts to the surface. In the same way, characteristic wings are noted in the delineated fingerprint for H⃛C/C⃛H contacts, which contribue 28.7% to the calculated Hirshfeld surface. The major contribution to the surface comes from H⃛H contacts at 52.7%. Smaller contributions but, at relatively long separations are made by H⃛N/N⃛H [6.2%] and C⃛C [3.8%] contacts.


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

Funding source: Osaka City University

Funding source: Sunway University

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

  2. Research funding: KF is grateful for support from the joint usage/research programme “Artificial Photosynthesis” based at Osaka City University. Sunway University Sdn Bhd is thanked for financial support of this work through Grant No. STR–RCTR–RCCM‐001–2019.

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

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Received: 2020-07-26
Accepted: 2020-09-08
Published Online: 2020-10-02
Published in Print: 2021-01-26

© 2020 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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  13. The crystal structure of (8R,10R,12R,14R)- 12-hydroxy-16-(5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)- 4,4,8,10,14-pentamethyltetradecahydro-3H- cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O5
  14. Structure of the mixed crystal (S)-(6-(bromo/chloro)-2-methoxy-2,6-dihydroquinolin-3-yl)(phenyl)methanol, C17H14Br0.5Cl0.5NO2
  15. The crystal structure of trans-tetraaqua-bis(4-acetylphenoxyacetato-κ1O)manganese(II), C20H26O12Mn
  16. Crystal structure of (E)-2-(4-fluoro-3-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  17. Crystal structure of DL-α-(methylaminomethyl)benzyl alcohol, C9H13NO
  18. The crystal structure of dipentaerthritol hexanitrate, C10H16N6O19
  19. Crystal structure of N,N-diphenylformamide, C13H11NO
  20. Crystal structure of (E)-2-(3,5-bis(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen- 1(2H)-one, C20H14F6O2
  21. Crystal structure of ortho-methoxy benzaldehyde, C8H8O2 – a second polymorph and deposition of 3D coordinates
  22. Crystal structure of catena-poly[diaqua-bis(μ2-2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O:O')-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O,O')yttrium(III)], C51H79O11Y
  23. Crystal structure of benzylthiouronium chloride, C8H11ClN2S
  24. Synthesis and crystal structure of tert-butyl (2′R,3R,3′R,4aR,9aS)-1-acetyl-5-chloro-3″-methyl-2,5″,9′-trioxo-1″-phenyl-1″,4a′,5″,9a′-tetrahydro-1′H,3′H,9′H-dispiro[indoline-3,4′-xanthene-2′,4″-pyrazole]-3′-carboxylate, C36H32ClN3O7
  25. Crystal structure of 2-hydroxy-4-methoxy benzaldehyde, C8H8O3
  26. Crystal structure of poly[diaqua-(m3-3′,5′-dicarboxy-[1,1′-biphenyl]-3,4-dicarboxylato-K4O,O′:O″:O‴) cadmium(II)], C16H11O10Cd
  27. Crystal structure of {tetraaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)}-{triaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)} – water – acetone (1/1/8/2)
  28. Synthesis and crystal structure of bis{2-bromo-6-((E)-((4-((E)-1-(methoxy-imino)ethyl)phenyl)imino)methyl)phenolato- κ2N,O}zinc(II)-methanol(1/2), C65H60Br4N8O9Zn2
  29. Crystal structure of benzenesulphonic acid
  30. Crystal structure of N-benzyl-N-nicotinoyl-nicotine amide C19H15N3O2
  31. Crystal structure of poly[aqua(μ3-2,4-diamino-benzenesulfonato-κ4N:N′,O:O′)silver(I)], C12H18O8N4S2Ag2
  32. Crystal structure of 1,4-bis(methylpyridinium benzene) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C26H18N6NiS4
  33. Crystal structure of the Cu(II) complex chlorido-(6-oxo-2-phenyl-1,6-dihydropyrimidine-4-carboxylato-k2N,O)-(phenanthroline-k2N,N')copper(II), C23H15ClCuN4O3
  34. Crystal structure of phenarsazine chloride acetic acid solvate, C14H13AsClNO2
  35. Crystal structure of poly[aqua-(μ2-3,3′,4,5′-biphenyl tetracarboxylate- κ3O,O′:O′′) -(μ2-4,4′-bis(pyrid-4-yl)biphenyl-κ2N:N′)zinc(II)], C27H18NO9Zn
  36. Crystal structure of catena-poly[(μ2-3-amino-benzenedisulfonato-κ2N:O)-bis (3-methyl-isoquinoline-κN)silver(I)], C26H24N3O3SAg
  37. Crystal structure of 2-((4-Aminophenyl)thio)acetic acid, C8H9NO2S
  38. Crystal structure of phenarsazine chloride dimethylsulfoxide solvate, C14H15AsClNOS
  39. Synthesis and crystal structure of 2-azido-N-phenylacetamide, C8H8N4O
  40. Crystal structure of chlorido{hydridotris[3-phenyl-5-methylpyrazol-1-yl-κN3]borato}copper(II), C30H28BClCuN6
  41. Crystal structure of benzanthrone – a redetermination for correct molecular geometry and localization of hydrogen atoms
  42. Crystal structure of 4-bromobenzaldehyde – complete redetermination at 200 K, C7H5BrO
  43. Crystal structure and spectroscopic properties of chlorido{hydridotris[3-,5-dimethylpyrazol-1-yl-κN3]borato}(3-,5-dimethylpyrazol-1-yl-κN)copper(II), C20H30BClCuN8
  44. The crystal structure of 4-((2-hydroxynaphthalen-1-yl)(pyrrolidin-1-yl)methyl)benzonitrile, C22H20N2O
  45. Crystal structure of 4-ethyl-3-phenylisoquinolin-1(2H)-one, C17H15NO
  46. Crystal structure of (tricyclohexylphosphane-κP)-[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-k1S]gold(I), C26H40AuFNOPS
  47. Crystal structure of (3S,8R,10R,12R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H54O4
  48. The crystal structure of 2-[(S)-1-(naphthalen-1-yl)ethyl]-2,3,7,7a- tetrahydro-3a,6-epoxyisoindol-1(6H)-one, C19H20NO2
  49. Crystal structure of {hydridotris[3-(t-butyl)-5-isopropylpyrazol-1-yl-κN3]borato}thallium(I), C30H52BN6Tl
  50. Synthesis and crystal structure of 1-octyl-3-phenylquinoxalin-2(1H)-one, C22H26N2O
  51. The crystal structure of 2,6-difluorophenol, C6H4F2O
  52. 4-(9H-Fluoren-9-yl)-4-methylmorpholin-4-ium bromide, C18H20BrNO
  53. The crystal structure of 2,4-dimethylimidazole monohydrate, C5H10N2O
  54. The crystal structure of 1,2-dimethylimidazole, C5H8N2
  55. The crystal structure of 3-ammonio-4-aminobenzoate, C7H8N2O2 – a second polymorph
  56. The crystal structure of 4-hydroxy-2,5-bis(1-methyl-1H-imidazol-3-ium-2-ylthio)-3,6-dioxocyclohexa-1,4-dienolate chloride monohydrate, C14H15N4O5S2Cl
  57. The crystal structure of butyrylferrocene, C14H16FeO
  58. The crystal structure of bi-1,1′-cyclopentane-1,1′-diol, C10H18O2
  59. The crystal structure of 2-iso-propylimidazole, C6H10N2
  60. The crystal structure of aqua-tris (1,3-diphenylpropane-1,3-dionato-κ2O,O′)-lanthanum(III), C45H35LaO7
  61. Crystal structure of (3E,5E)-3,5-bis-4-methoxy-3-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  62. The crystal structure of 3,5-dichloro-6-diazo-2,4-dinitrocyclohexa-2,4-dien-1-one, C6Cl2N4O5
  63. Crystal structure of carbonyl(2-methylquinolin-8-olato-κ2N,O)(triphenylarsine-κAs)rhodium(I), C29H23AsNO2Rh
  64. Crystal structure of (1aS,1a1S,2S)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl-4-nitrobenzoate, C22H25NO5
  65. Crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-k2O,O′)(triphenylarsine-κAs)rhodium(I), C24H19AsNO3Rh
  66. Crystal structure of catena-poly[triqua-bis(μ2-4-carboxy-2-(1H-tetrazol-1-yl)-1H-imidazole-5-carboxylato-k3N,O:O′)barium(II)] tetrahydrate, C14H14BaN12O15
  67. Crystal structure of (E)-3′,6′-bis(ethylamino)-2-((quinoxalin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C35H32N6O2
  68. Crystal structure of diaqua-bis(μ2-5-chloro-salicylato-κ3O,O′:O′)-bis(5-chloro-salicylato-κ2O,O′)-bis(1,10-phenanthroline-κ2N,N′) dilead(II) – water (1/2), C52H36C14N4O14Pb2·2(H2O)
  69. Crystal structure of (E)-2-(4-ethoxycarbonyl-3,5-dimethyl-2-(pyrrole-2-ylmethyleneamino)-3′,6′-dihydroxylspiro[isoindoline-1,9′-xanthen]-3-one-methanol (1/1), C31H29N3O7
  70. The crystal structure of 5H-dibenzo[b,e]azepine-6,11-dione, C14H9NO2
  71. Crystal structure of (E)-2-(4-fluoro-2-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  72. The crystal structure of N-(2-methoxy-4,5-bis[phenylselanyl]phenyl)picolinamide, C25H20N2O2Se2
  73. The crystal structure of (E)-2-(5-bromo-2-hydroxybenzylidene)-N-phenylhydrazine-1- carboxamide monohydrate, C14H14BrN3O3
  74. Crystal structure of fac-tricarbonyl-(nitrato-k1O)-bis(pyridine-κN)-rhenium, C13H10O6N3Re
  75. Crystal structure of (E)-2-(((1H-pyrrol-2-yl)methylene)amino)-3′,6′-dihydroxyspiro[isoindoline-1,9′-xanthen]-3-one — methanol (1/2), C27H25N3O6
  76. The crystal structure of 4-amino-N′-(4-aminobenzoyl)benzohydrazide monohydrate, C14H16N4O3
  77. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 5-hydroxyisophthalate monohydrate, C12H20N8O6S2
  78. The crystal structure of 2-(chloromethyl)pyridine, C6H6ClN
  79. The crystal structure of 1-bromo-4-iodo-benzene, C6H4BrI
  80. The crystal structure of 2,6-dimethyl-4-nitro-phenol, C8H9NO3
  81. The crystal structure of 3-chloropropionic acid, C3H5ClO2
  82. The crystal structure of 2-(2-methoxyphenyl)acetic acid, C9H10O3
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