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Crystal structure of n-butyl-tris(dicyclo-hexylamido)hafnium(IV), C40H75HfN3

  • Christian Adler , Marc Schmidtmann and Rüdiger Beckhaus EMAIL logo
Published/Copyright: May 4, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 4

Abstract

C40H75HfN3, monoclinic, P21/n (no. 14), a = 10.7446(3) Å, b = 13.6547(4) Å, c = 26.5464(9) Å, β = 92.2375(15)°, V = 3891.8(2) Å3, Z = 4, Rgt(F) = 0.0195, wRref(F2) = 0.0461, T = 100(2) K.

CCDC no.:: 1542041

The asymmetric unit of the title crystal structure is shown in the figure (hydrogen atoms are omitted for clarity). Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.36 × 0.36 × 0.32 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:27.1 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:76°, >99%
N(hkl)measured, N(hkl)unique, Rint:225553, 20900, 0.022
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 19301
N(param)refined:398
Programs:SHELX [1], Bruker programs [2]
Table 2:

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

AtomxyzUiso*/Ueq
Hf10.41335(2)0.76960(2)0.11955(2)0.00992(1)
N10.47000(7)0.62661(6)0.12569(3)0.01208(13)
N20.22680(8)0.78168(6)0.10233(3)0.01219(13)
N30.46600(8)0.85440(6)0.18020(3)0.01237(13)
C10.60777(9)0.62364(7)0.12819(4)0.01329(15)
H10.63610.69320.13120.016*
C20.66360(9)0.57003(8)0.17489(4)0.01623(16)
H2A0.62710.59710.20560.019*
H2B0.64160.49970.17280.019*
C30.80570(10)0.58074(9)0.17898(5)0.0212(2)
H3A0.82740.65030.18490.025*
H3B0.83870.54230.20820.025*
C40.86654(11)0.54538(10)0.13121(5)0.0247(2)
H4A0.95700.55940.13380.030*
H4B0.85560.47360.12790.030*
C50.80913(11)0.59594(9)0.08458(5)0.0221(2)
H5A0.84610.56860.05400.027*
H5B0.82880.66670.08600.027*
C60.66744(10)0.58236(9)0.08089(4)0.01835(18)
H6A0.64740.51180.07750.022*
H6B0.63280.61660.05060.022*
C70.40903(9)0.53027(7)0.12424(4)0.01355(15)
H70.47100.48110.13750.016*
C80.36691(10)0.49809(8)0.07081(4)0.01663(17)
H8A0.30590.54590.05650.020*
H8B0.43960.49740.04900.020*
C90.30760(12)0.39625(9)0.07093(4)0.02057(19)
H9A0.27740.37940.03630.025*
H9B0.37120.34730.08170.025*
C100.19903(12)0.39196(9)0.10627(5)0.0227(2)
H10A0.16820.32380.10800.027*
H10B0.13020.43340.09250.027*
C110.23708(12)0.42695(9)0.15927(4)0.0212(2)
H11A0.29620.37940.17510.025*
H11B0.16250.42950.18000.025*
C120.29799(10)0.52817(8)0.15863(4)0.01693(17)
H12A0.32640.54620.19330.020*
H12B0.23570.57720.14680.020*
C130.21032(9)0.75034(7)0.04917(4)0.01308(15)
H130.28950.71630.04110.016*
C140.10656(10)0.67473(8)0.03891(4)0.01632(16)
H14A0.11550.62060.06360.020*
H14B0.02450.70600.04320.020*
C150.11261(12)0.63366(9)−0.01464(4)0.0212(2)
H15A0.19130.5969−0.01770.025*
H15B0.04270.5875−0.02090.025*
C160.10565(13)0.71478(10)−0.05421(5)0.0248(2)
H16A0.02200.7452−0.05460.030*
H16B0.11790.6862−0.08790.030*
C170.20469(13)0.79331(10)−0.04327(4)0.0231(2)
H17A0.28850.7649−0.04720.028*
H17B0.19360.8475−0.06780.028*
C180.19518(11)0.83334(8)0.01023(4)0.01709(17)
H18A0.11320.86530.01360.021*
H18B0.26070.88320.01670.021*
C190.11512(9)0.81571(8)0.12730(4)0.01483(15)
H190.04320.77520.11450.018*
C200.08316(11)0.92372(9)0.11686(4)0.02080(19)
H20A0.15490.96510.12780.025*
H20B0.06830.93320.08010.025*
C21−0.03235(12)0.95645(11)0.14440(5)0.0276(3)
H21A−0.04921.02640.13710.033*
H21B−0.10540.91800.13200.033*
C22−0.01346(11)0.94214(10)0.20110(5)0.0238(2)
H22A−0.09060.96050.21800.029*
H22B0.05450.98530.21410.029*
C230.01906(12)0.83571(10)0.21313(5)0.0249(2)
H23A−0.05420.79400.20460.030*
H23B0.03820.82930.24980.030*
C240.13045(11)0.79887(8)0.18427(4)0.01809(17)
H24A0.14160.72790.19070.022*
H24B0.20670.83280.19710.022*
C250.44877(9)0.95792(7)0.16540(4)0.01409(15)
H250.40390.95670.13170.017*
C260.36608(10)1.01802(8)0.19989(5)0.01922(18)
H26A0.28680.98270.20440.023*
H26B0.40861.02530.23340.023*
C270.33837(12)1.11967(9)0.17762(6)0.0267(2)
H27A0.28911.11260.14550.032*
H27B0.28821.15770.20120.032*
C280.45894(13)1.17459(9)0.16809(6)0.0289(3)
H28A0.43891.23800.15160.035*
H28B0.50331.18840.20070.035*
C290.54318(13)1.11567(10)0.13491(5)0.0259(2)
H29A0.62251.15130.13110.031*
H29B0.50271.10780.10100.031*
C300.57017(10)1.01465(8)0.15781(4)0.01818(17)
H30A0.61591.02240.19070.022*
H30B0.62360.97700.13520.022*
C310.51963(9)0.83741(7)0.23106(4)0.01325(15)
H310.50510.89760.25140.016*
C320.66064(9)0.81862(8)0.23196(4)0.01644(16)
H32A0.67800.76250.20970.020*
H32B0.70310.87690.21860.020*
C330.71334(10)0.79679(10)0.28522(5)0.02072(19)
H33A0.80310.78130.28380.025*
H33B0.70480.85560.30660.025*
C340.64561(11)0.71081(9)0.30888(4)0.02002(19)
H34A0.66140.65030.28960.024*
H34B0.67810.70090.34390.024*
C350.50579(11)0.73036(10)0.30892(4)0.0213(2)
H35A0.48980.78670.33120.026*
H35B0.46310.67240.32250.026*
C360.45243(10)0.75231(8)0.25595(4)0.01631(16)
H36A0.36290.76850.25780.020*
H36B0.45950.69300.23480.020*
C370.50835(10)0.83298(8)0.05218(4)0.01800(17)
H37A0.47860.79400.02270.022*
H37B0.47370.89960.04720.022*
C380.64836(11)0.84276(11)0.04786(5)0.0240(2)
H38A0.68690.77770.05370.029*
H38B0.68060.88700.07490.029*
C390.68963(13)0.88184(13)−0.00260(6)0.0342(3)
H39A0.65720.8383−0.02990.041*
H39B0.65300.9476−0.00840.041*
C400.83016(14)0.88879(14)−0.00522(8)0.0417(4)
H40A0.85170.9132−0.03850.063*
H40B0.86700.82380.00030.063*
H40C0.86250.93390.02090.063*

Source of material

All reactions were carried out under a dry nitrogen atmosphere using Schlenk-technique. Tris(dicyclohexylamido)hafnium(IV) chloride is easily available by a literature known synthesis [3]. The reaction with n-butyllithium was carried out according to the procedure known for the analogous zirconium complex [4]. To a solution of (Cy2N)3HfCl (500 mg, 0.662 mmol) in 20 mL n-hexane was added a n-butyllithium solution in n-hexane (0.27 mL, 0.662 mmol, 2.5 mol/l). The resulting mixture was stirred at ambient temperature. The mixture was filtered over a pad of celite and concetrated to 10 mL. Colourless crystals were obtained from this solution at −30 °C after three days, identified as the title compound n-butyl-tris(dicyclohexylamido)hafnium(IV).

Experimental details

All hydrogen atoms were located in the difference Fourier syntheses, and subsequently fixed to geometric positions using appropiate riding models.

Comment

The title compound is a rare example of a structural characterized hafnium complex with a terminal n-butyl group. The complex n-BuHf(NCy2)3 is the first structural characterized hafnium-n-butyl complex employing three amido ligands at the electron deficient metal center. It is isostructural to the analogous zirconium compound [4]. There are only three other examples for related hafnium complexes listed in the Cambridge Crystallographic Database [5], [6], [7]. One of them is the recently published crystal structure of Di-n-butylbis(η5-pentamethyl-cyclopentadienyl)hafnium(IV) [5]. Di-n-butylbis(η5-cyclopentadienyl)hafnium(IV) (Cp2Hf(n-Bu)2) is known and used as a Hf(II) source at elevated temperatures (100 °C), analogues to the Negishi System Cp2ZrCl2/n-BuLi which eliminates butane and 1-butene to give the free metallocene [8, 9] . Analogous to Cp2Hf(n-Bu)2 the complex n-BuHf(NCy2)3 is remarkably robust. There are no hints for a β-agostic interaction in the molecular structure. The angle Hf(1)-C(37)-C(38) is 124.84(8)° and thereby within the range for non-agostic compounds [10, 11] . The metal-carbon σ-bond Hf(1)-C(37) (2.2653(11) Å) is within the expected range for such a bond. The hafnium-nitrogen bonds are very similar (Hf(1)-N(1) 2.0497(8) Å, Hf(1)-N(2) 2.0450(8) Å, Hf(1)-N(3) 2.0451(8) Å). These bond lengths are shortened in comparison to a typical single bond due to attractive interactions between the nitrogen lone pair and the electron deficient metal center [12]. All nitrogen atoms are coordinated trigonal planar (sum of all angles: N1 359.8°, N2 359.9°, N3 359.9°).

References

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Received: 2016-11-29
Accepted: 2017-4-5
Published Online: 2017-5-4
Published in Print: 2017-7-26

©2017 Christian Adler et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  49. Crystal structure of methyl (E)-2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazine-1-carboxylate, C13H19N3O3
  50. The crystal structure of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate, C10H15N3O2
  51. Crystal structure of 1,1-bis(η5-adamantylcyclopentadienyl)-3-phenyl-2-trimethylsilyl-2,3-dihydroisotitanazole, C42H55NSiTi
  52. Crystal structure of 2-(4-(2-(4-benzylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C28H29N3O2
  53. Important impurity of Flupirtine – a single crystal study on ethyl (6-amino-5-((ethoxycarbonyl)amino)pyridin-2-yl)(4-fluorobenzyl)carbamate, C18H21FN4O4
  54. Crystal structure of ethyl 3-(4-methoxyphenyl)-1-(2-(4-methoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate, C22H22N2O5
  55. Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10
  56. The crystal structure of the inner salt of 2-[(aminoiminomethyl)amino]ethylcarbamic acid [systematic name: (2-((diaminomethylene)ammonio)ethyl)carbamate], C4H10N4O2
  57. Crystal structure of (8-hydroxy-5-nitroquinolinium) perchlorate – 8-hydroxy-5-nitroquinoline (1/1), C18H13ClN4O10
  58. The crystal structure of (5-methyl-1,2,4-oxadiazol-3-yl)ferrocene, C13H12FeN2O
  59. Crystal structure of methyl 1-(2-(fluorosulfonyl)ethyl)-2-oxocyclopentanecarboxylate, C9H13FO5S
  60. Crystal structure of the triclinic modification of 1-methyl-4-nitroimidzole, C4H5N3O2
  61. Corrigendum
  62. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
https://doi.org/10.1515/ncrs-2016-0380
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)manganese(II)] bis(4-chlorobenzenesulfonate) – 4,4′-bipyridine – water (1/1/2) C42H40Cl2MnN6O10S2
  3. The crystal structure of 1,2-bis[2-methyl-5-(3-cyanophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H16F6N2S2
  4. Crystal structure of the first characterized polymeric copper and sodium complex diaqua-(tris-acetato-κO,O′)(μ2-acetato-κO′′)dinatrium copper(II) monohydrate, C8H18CuNa2O11
  5. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-3-yl-methylene)aniline, C18H22N2
  6. Crystal structure of methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22N2O5
  7. Crystal structure of bis(1,3-bis(diphenylphosphino)propane-κ2P,P′)silver(I) trifluorosulfonate–methanol (1:0.5), [Ag(C27H26P2)]SO3CF3⋅0.5CH3OH
  8. Crystal structure of μ-1,4-bis(diphenylphosphine)butane-2,9-dimethyl-1,10-phenanthroline-κ2N:N′-bis(cyano-κC)dicopper(I)]-water, C58H56Cu2N6O2P2
  9. Crystal structure of N2,N6-bis(1-hydrazinyl-2-methyl-1-oxopropan-2-yl) pyridine-2,6-dicarboxamide, C15H23N7O4
  10. Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2
  11. Crystal structure of diaqua-(2,2′-(butane-1,4-diyl)-bis(5-carboxy-1H-imidazole-4-carboxylato)-κ4O,O′,N,N′)cadmium(II) monohydrate, C14H18O11N4Cd
  12. Crystal structure of ethyl (E)-3-(cyclopropylamino)-2-(2,4-dichloro-5-fluorobenzoyl) acrylate, C15H14Cl2FNO3
  13. Crystal structure of bis-(1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-ol-κ2O,O′)-(N,N-dimethylformamide)zinc(II), C43H31Cl2N5O5S2Zn
  14. Crystal structure of tetrakis(μ3-2-(N-(2-hydroxyethyl)amino)ethoxo)-tetrachloro-tetra-cobalt(II) methanol solvate, C17H44Cl4Co4N4O9
  15. Crystal structure of 3-amino-1-(4-bromophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrile, C21H15BrN2O2
  16. Crystal structure of 2-amino-4-(4-isopropyl-phenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene, C22H18N2O3
  17. Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C22H18N2O3
  18. Crystal structure of monoaqua-[6,6′-((1E,1′E)-(1,2-phenylene bis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-nitrophenolato-κ4N,N′,O,O′)]zinc(II), C20H12Br2N4O7Zn
  19. Crystal structure of 11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one – acetonitril (1/2), C33H41N3O2
  20. Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C11H15NO3S
  21. Crystal structure of catena-poly{diaqua-bis(3-(1H-1,2,4-triazol-1-yl)benzoato-κ2O:N)copper(II)} monohydrate, C18H18CuN6O7
  22. Crystal structure of tetraaqua-bis(3-(4H-1,2,4-triazol-4-yl)benzoato-κN)cobalt(II), C18H20CoN6O8
  23. The crystal structure of 4-bromo-N-cyclopropyl-2,5-difluorobenzenesulfonamide, C9H8BrF2NO2S
  24. Crystal structure of ([3,3′-bipyridine]-6,6′-dicarboxylato-κ2O:O′)-bis(1,2-bis(4-pyridyl)ethane-κ2N:N′)disilver(I) dihydrate, C37H35Ag2N5O6
  25. The crystal structure of (4-(1H-1,2,4-triazol-1-yl)benzoato-κN)-[4-(1H-1,2,4-triazol-1-yl)benzoic acid-κN]silver(I), C18H13AgN6O4
  26. Crystal structure of 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2
  27. Crystal structure of bis(2-((E)-((4-((E)-1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-methoxyphenolato-κ2O,N)copper(II), C36H38CuN4O6
  28. Crystal structure of poly[1,2-bis(1,2,4-triazol-4-yl)ethane-κ2N:N′]silver(I) bromate monohydrate]silver(I), C6H10AgBrN6O4
  29. The crystal structure of 2,3,5-triphenyl-2,3-dihydro-1H-tetrazol-1-ium 2,3-dioxoindoline-5-sulfonate, C27H19N5O5S
  30. Crystal structure of 3-(2-amino-1,3-selenazol-4-yl)-2H-chromen-2-one – dimethylformamide (1/1), C15H15N3O3Se
  31. Crystal structure of diethyl 3,3′-(diazene-1,2-diyl)(E)-dibenzoate, C18H18N2O4
  32. Crystal structure of cis-bis((1H-benzimidazol-2-yl)methanol-κN,O)-bis(isothiocyanato-κN)nickel(II), C18H16N6NiO2S2
  33. Crystal structure of bis(2-(2′-hydroxy-5′-methoxyphenyl)-1H-benzimidazole)boron – tetrahydrofuran (1/1), C36H37N4O6B
  34. Crystal structure of poly[aqua-bis(nitrato-κ2O,O′)-(μ3-1,3-benzimidazol-3-ium-1,3-diacetato-κ4O,O′:O′′:O′′′)dysprosium(III)], C11H11DyN4O11
  35. Crystal structure of n-butyl-tris(dicyclo-hexylamido)hafnium(IV), C40H75HfN3
  36. Crystal structure of (E)-1-[1-(3-chloro-4-fluoro-phenyl)ethylidene]-2-(2,4-dinitrophenyl)hydrazine, C28H20Cl2F2N8O8
  37. The crystal structure of ethyl 4-((2-hydroxybenzyl)amino)benzoate, a Schiff base, C16H17NO3
  38. Crystal structure of 3-(2-(4-isobutylphenyl)propanoyl)-1-methylimidazolidine-2,4-dione, C17H22N2O3
  39. Crystal structure of poly[(μ3-2-(pyrazin-2-ylthio)acetato-κ3N:O:S)silver(I)], C6H5AgN2O2S
  40. Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl)ethanone O-benzyl oxime, C26H22N2O2
  41. Crystal structure of (E)-2,3-dihydroxybenzaldehyde O-(2-((((E)-1-(2,5-dihydroxyphenyl)ethylidene)amino)oxy)ethyl) oxime monohydrate, C17H20N2O7
  42. Crystal structure of 4-(chloromethyl)-3-nitrobenzoic acid, C8H6ClNO4
  43. Crystal stucture of 4-((10H-phenothiazin-10-yl)methyl)-2,6-di-tert-butylphenol, C27H31NOS
  44. The crystal structure of ethyl 1-(4-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C13H10F3N3O4
  45. Crystal structure of catena-poly[di-(μ3-oxido-κ3O:O:O)-tetraoxido-(μ2-5′-(pyrazin-2-yl)-1H,2′H-3,3′-bi(1,2,4-triazole)-κ2N:N′)dimolybdenum(VI)], C8H6Mo2N8O6
  46. Crystal structure of (3,6-dioxocyclohexa-1,4-diene-1,4-bis(olato)-κ4O,O′:O′′,O′′′)-bis(tris(2-pyridylmethyl)amine-κ4N,N′,N′′,N′′′))-dizinc(II) bis(hexafluorophosphate(V)), C42H38F12N8O4P2Zn2
  47. Crystal structure of catena-poly[hexakis(μ2-2-acetylphenolato-κ3O:O,O′)trimanganese(II)], C48H42Mn3O12
  48. The crystal structure of 2,2-difluoro-4-(trifluoromethyl)-2,5-dihydro-[1,3,2]dioxaborinino[5,4-c]chromen-3-ium-2-uide, C11H6BF5O3
  49. Crystal structure of methyl (E)-2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazine-1-carboxylate, C13H19N3O3
  50. The crystal structure of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate, C10H15N3O2
  51. Crystal structure of 1,1-bis(η5-adamantylcyclopentadienyl)-3-phenyl-2-trimethylsilyl-2,3-dihydroisotitanazole, C42H55NSiTi
  52. Crystal structure of 2-(4-(2-(4-benzylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C28H29N3O2
  53. Important impurity of Flupirtine – a single crystal study on ethyl (6-amino-5-((ethoxycarbonyl)amino)pyridin-2-yl)(4-fluorobenzyl)carbamate, C18H21FN4O4
  54. Crystal structure of ethyl 3-(4-methoxyphenyl)-1-(2-(4-methoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate, C22H22N2O5
  55. Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10
  56. The crystal structure of the inner salt of 2-[(aminoiminomethyl)amino]ethylcarbamic acid [systematic name: (2-((diaminomethylene)ammonio)ethyl)carbamate], C4H10N4O2
  57. Crystal structure of (8-hydroxy-5-nitroquinolinium) perchlorate – 8-hydroxy-5-nitroquinoline (1/1), C18H13ClN4O10
  58. The crystal structure of (5-methyl-1,2,4-oxadiazol-3-yl)ferrocene, C13H12FeN2O
  59. Crystal structure of methyl 1-(2-(fluorosulfonyl)ethyl)-2-oxocyclopentanecarboxylate, C9H13FO5S
  60. Crystal structure of the triclinic modification of 1-methyl-4-nitroimidzole, C4H5N3O2
  61. Corrigendum
  62. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
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