Startseite Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
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Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3

  • See Mun Lee , Kong Mun Lo und Edward R.T. Tiekink ORCID logo EMAIL logo
Veröffentlicht/Copyright: 10. September 2019
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 234 Heft 6

Abstract

C16H15ClN2O3, orthorhombic, Pbca (no. 61), a = 18.7178(2) Å, b = 15.2296(2) Å, c = 32.0558(3) Å, V = 9137.97(18) Å3, Z = 24, Rgt(F) = 0.0407, wRref(F2) = 0.1099, T = 100(2) K.

CCDC no.: 1946616

The three molecules comprising the asymmetric unit are 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:Yellow block
Size:0.30 × 0.24 × 0.12 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:2.35 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:76.6°, >99%
N(hkl)measured, N(hkl)unique, Rint:31906, 9519, 0.034
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 8480
N(param)refined:616
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.70677(3)0.23421(4)0.08440(2)0.04725(13)
Cl21.02412(3)0.40652(4)0.45858(2)0.04883(14)
Cl30.70514(2)0.96072(3)0.10114(2)0.03421(11)
O10.51429(6)0.28828(8)0.38072(3)0.0256(2)
H1O0.5356(11)0.2820(15)0.3580(4)0.038*
O20.46888(6)0.29100(8)0.45669(3)0.0294(2)
O30.52798(6)0.26789(8)0.26463(3)0.0255(2)
O40.67005(6)0.56582(8)0.23750(3)0.0264(2)
H4O0.6892(12)0.5517(15)0.2602(4)0.040*
O50.59621(7)0.59094(8)0.16997(4)0.0328(3)
O60.80607(7)0.56269(10)0.31806(4)0.0396(3)
O70.67117(5)0.64894(7)0.37859(3)0.0218(2)
H7O0.6634(12)0.6760(13)0.3561(4)0.033*
O80.67684(6)0.54346(8)0.44266(3)0.0283(2)
O90.71534(5)0.78524(8)0.29089(3)0.0241(2)
N10.61641(6)0.26216(8)0.32920(4)0.0198(2)
H2N0.6870(5)0.2555(13)0.2839(6)0.024*
N20.64083(6)0.25484(9)0.28917(4)0.0206(2)
N30.67912(7)0.49141(9)0.30934(4)0.0255(3)
N40.72222(8)0.46748(9)0.34182(4)0.0262(3)
H4N0.7052(11)0.4381(13)0.3631(5)0.031*
N50.60035(7)0.70692(8)0.31556(4)0.0198(2)
N60.60059(6)0.75046(8)0.27797(4)0.0196(2)
H6N0.5608(7)0.7556(13)0.2637(5)0.023*
C10.56437(8)0.27817(10)0.41057(4)0.0199(3)
C20.54069(8)0.27973(10)0.45242(5)0.0218(3)
C30.58974(9)0.26936(10)0.48449(5)0.0246(3)
H30.57420.27170.51270.030*
C40.66195(9)0.25553(11)0.47545(5)0.0263(3)
H40.69500.24730.49760.032*
C50.68583(8)0.25371(10)0.43487(5)0.0232(3)
H50.73510.24480.42910.028*
C60.63712(8)0.26512(9)0.40187(4)0.0189(3)
C70.66222(7)0.25704(10)0.35905(4)0.0195(3)
H70.71150.24820.35330.023*
C80.59214(8)0.25925(10)0.25817(4)0.0196(3)
C90.62332(7)0.25333(10)0.21538(4)0.0203(3)
C100.59394(8)0.30620(11)0.18417(5)0.0252(3)
H100.55610.34560.19060.030*
C110.62024(9)0.30093(12)0.14376(5)0.0296(3)
H110.60090.33680.12230.036*
C120.67504(9)0.24271(12)0.13525(5)0.0296(3)
C130.70541(9)0.19004(12)0.16578(5)0.0274(3)
H130.74320.15080.15920.033*
C140.67928(8)0.19604(10)0.20624(4)0.0233(3)
H140.69960.16100.22770.028*
C150.43933(10)0.29242(15)0.49749(5)0.0374(4)
H15A0.45210.34790.51180.045*
H15B0.45830.24280.51410.045*
C160.35951(10)0.28498(14)0.49350(6)0.0378(4)
H16A0.34170.33170.47520.057*
H16B0.33750.29070.52110.057*
H16C0.34720.22770.48160.057*
C170.60095(9)0.53996(10)0.23869(5)0.0250(3)
C180.55938(9)0.55638(11)0.20300(5)0.0284(3)
C190.48673(10)0.53751(12)0.20322(6)0.0341(4)
H190.45830.55080.17950.041*
C200.45546(10)0.49912(13)0.23816(6)0.0375(4)
H200.40550.48790.23840.045*
C210.49641(10)0.47738(11)0.27228(6)0.0331(4)
H210.47500.44890.29550.040*
C220.56960(9)0.49704(10)0.27305(5)0.0265(3)
C230.61245(9)0.47228(10)0.30918(5)0.0267(3)
H230.59130.44260.33210.032*
C240.78782(9)0.50665(11)0.34305(5)0.0277(3)
C250.83791(9)0.47564(11)0.37638(5)0.0255(3)
C260.86842(11)0.53822(11)0.40257(5)0.0337(4)
H260.85130.59690.40200.040*
C270.92309(11)0.51612(12)0.42936(5)0.0346(4)
H270.94290.55850.44770.041*
C280.94831(10)0.43126(12)0.42892(5)0.0326(4)
C290.91801(12)0.36699(12)0.40424(6)0.0377(4)
H290.93540.30840.40510.045*
C300.86141(11)0.38974(11)0.37805(5)0.0332(4)
H300.83900.34610.36140.040*
C310.56162(11)0.58467(13)0.13011(6)0.0360(4)
H31A0.51960.62410.12920.043*
H31B0.54520.52380.12520.043*
C320.61505(12)0.61098(15)0.09745(6)0.0431(4)
H32A0.63080.67140.10260.065*
H32B0.59290.60740.06980.065*
H32C0.65630.57140.09860.065*
C330.60971(8)0.60769(10)0.38903(4)0.0204(3)
C340.61165(8)0.55055(10)0.42375(5)0.0237(3)
C350.55008(9)0.50664(11)0.43577(5)0.0294(3)
H350.55130.46860.45930.035*
C360.48643(9)0.51764(12)0.41383(6)0.0326(4)
H360.44460.48760.42260.039*
C370.48397(9)0.57194(11)0.37944(5)0.0283(3)
H370.44050.57900.36450.034*
C380.54564(8)0.61702(10)0.36634(5)0.0220(3)
C390.54352(8)0.66727(10)0.32763(5)0.0217(3)
H390.50090.67060.31170.026*
C400.66375(7)0.78660(9)0.26694(4)0.0194(3)
C410.66906(7)0.82919(10)0.22515(4)0.0197(3)
C420.72202(8)0.89326(10)0.22056(5)0.0230(3)
H420.75090.90870.24380.028*
C430.73302(8)0.93446(11)0.18268(5)0.0252(3)
H430.76860.97850.17970.030*
C440.69057(8)0.90969(11)0.14913(5)0.0241(3)
C450.63763(8)0.84671(11)0.15254(5)0.0237(3)
H450.60910.83150.12910.028*
C460.62692(7)0.80602(10)0.19093(4)0.0213(3)
H460.59090.76250.19380.026*
C470.68035(10)0.48873(12)0.47914(5)0.0333(4)
H47A0.66400.42860.47240.040*
H47B0.64920.51270.50130.040*
C480.75665(11)0.48689(15)0.49370(6)0.0435(5)
H48A0.78670.46070.47200.065*
H48B0.76010.45190.51930.065*
H48C0.77280.54690.49930.065*

Source of material

General: The melting point of the compound was measured on a Electrothermal digital melting point apparatus and was uncorrected. The elemental analysis was performed on a Perkin-Elmer EA2400 CHN analyser. The IR spectrum was recorded using a Perkin-Elmer RX1 spectrophotometer equipped as a Nujol mull in between KBr cell from 4000 to 400 cm−1. The 1H and 13C{1H} NMR spectra were recorded in CDCl3 solution on a Bruker AVN FT-NMR 400 MHz NMR spectrometer with chemical shifts relative to tetramethylsilane.

Synthesis: 4-Chlorobenzhydrazide (Fluka, 0.85 g, 5.0 mmol) and 3-ethoxysalicylaldehyde (Aldrich, 0.83 g, 5.0 mmol) were dissolved in methanol (50 mL) and refluxed for 3 h. The mixture was filtered and allowed to stand at room temperature for 2 days whereupon yellow crystals were formed. The crystals were filtered, washed with methanol and air-dried. Yield: 1.35 g (84.7%). M.pt: 433–434 K. Calcd for C16H15ClN2O3: C 60.29; H 4.74; N 8.79%. Found: C 60.24; H 4.34; N, 8.78%. IR (cm−1): 3448 (br) ν(O—H), 3217 (s) ν(N—H), 1655 (s) ν(C=O), 1610 (s) ν(C=N). 1H NMR (CDCl3, ppm): δ 1.39 (s, 3H, CH3), 3.98–4.08 (m, 2H, OCH2), 6.77–7.17 (m, 3H, Ar—H), 7.59–7.93 (m, 4H, Ph—H), 8.63 (s, 1H, HCN), 10.88 (s, 1H, N—H), 12.15 (s, 1H, O—H). 13C{1H} NMR (CDCl3, ppm): δ 14.7 (CH3), 64.2 (CH2), 115.4, 118.9, 119.1, 121.0, 128.6, 129.5, 131.5, 136.8, 147.0, 147.5 (Ar—C).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The O- and N-bound H-atoms were located in a difference Fourier map but were refined with distance restraints of O—H = 0.84±0.01 Å and N—H = 0.88±0.01 Å, respectively, and with Uiso(H) set to 1.5Ueq(O) and 1.2Ueq(N), respectively.

Comment

Crystal structure determinations of neutral benzyltin compounds containing Schiff base ligands related to the title hydrazone molecule, 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene] benzohydrazide, a potentially dianionic tridentate ligand, have sometimes revealed unexpected synthetic outcomes. Thus, while the anticipated (2-FC6H4CH2)2Sn(L1) product was obtained from the reaction of (2-FC6H4CH2)2SnCl2 and 4-chloro-N′-[(1E)-(5-chloro-2-hydroxyphenyl)methylidene] benzohydrazide (H2L1) [5], incompletely substituted species of composition (C6H5CH2)Sn(OHCH3)(L2)Cl [6] and (4-FC6H4CH2)Sn(OH2)(L3)Cl [7] were obtained when analogous reactions of the respective di-(substituted-benzyl)tin dichlorides with 4-chloro-N′-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide (H2L2) and 1-hydroxy-N′-[(1E)-(2-hydroxy-4-methoxyphenyl) methylidene]naphthalene-2-carbohydrazide (H2L3), respectively, were conducted. Studies in this area are largely motivated by the biological activity, especially in the context of the quest for new anti-cancer drugs, of organotin derivatives of these molecules [8], [9], [10]. Complementing the above, are structural studies of the Schiff bases themselves [11], [12] and it was in this context that the title compound was studied crystallographically.

The crystallographic asymmetric unit of the title structure comprises three independent molecules as shown in the figure (70% displacement ellipsoids). Each independent molecule, hereafter designated as the Cl1-, Cl2- and Cl3-molecules, comprises a central chromophore defined by the C(=O)N(H)N=C atoms which is planar with r.m.s. deviations of 0.0068 and 0.0171 Å for the Cl1 and Cl3 molecules, respectively. However, a difference in conformation for the Cl2-molecule is noted whereby a twist is evident as seen in the C23—N3—N4—C24 torsion angle of −166.67(14)°. The configuration about each of the imine-N1—C7 [1.2871(19) Å], N3—C23 [1.282(2) Å] and N5—C39 [1.283(2) Å] bonds is E. The dihedral angles between the central planes and appended hydroxy- and chloro-phenyl rings also reveal differences in conformation between the independent molecules, i.e. 4.49(3) & 38.97(7)°, 18.47(11) & 59.73(7)° and 9.83(10) and 25.05(7)°, for the Cl1–Cl3-molecules, respectively. The dihedral angles formed between the outer rings are 35.36(6), 77.69(6) and 31.3(7)°, respectively. Each molecule features an intramolecular hydroxy-O—H⋯N(imine) hydrogen bond [O1—H1o⋯N1: H1o⋯N1 = 1.798(19) Å, O1⋯N1 = 2.5572(16) Å with angle at H1o = 150.3(18) Å, O4—H4o⋯N3: H4o⋯N3 = 1.833(16) Å, O4⋯N3 = 2.5722(17) Å with angle at H4o = 146(2)° and O7—H7o⋯N5: H7o⋯N5 = 1.818(18) Å, O7⋯N5 = 2.5728(16) Å with angle at H7o = 148(2)°].

The crystal of the title compound features supramolecular, zig-zag chains along the a-axis direction sustained by amide-N—H⋯O(carbonyl) hydrogen bonds occurring between the Cl1- and Cl3-molecules [N2—H2n⋯O9i: H2n⋯O9i = 1.897(10) Å, N2⋯O9i = 2.7323(15) Å with angle at H2n = 157.8(18)° and N6—H6n⋯O3ii: H6n⋯O3ii = 1.903(14) Å, N6⋯O3ii = 2.7797(16) Å with angle at H6n = 177.1(15)° for symmetry operations (i) 3/2 − x, −1/2 + y, z and (ii) 1 − x, 1/2 + y, 1/2 − z]. Additional stability to the chains is afforded by π-stacking interactions between chlorophenyl rings [Cg(C9–C14)⋯Cg(C41–C46)i = 3.7110(9) Å with an angle of inclination = 2.52(8)°] The amide-N4H atom of the Cl2-molecule does not participate in a hydrogen bond. The chains are linked into supramolecular layers in the ab-plane via a combination of parallel carbonyl-O⋯π(hydroxyphenyl) [C8—O3⋯Cg(C17–C22)iii = 3.9502(14) Å with angle at O3 = 98.81(9)° for (iii) 1 − x, −1/2 + y, 1/2 − z] and C—H⋯O interactions with the closest of these being of the type methylene-C—H⋯O(hydroxy) [C31—H31a⋯O1ii: H31a⋯O1ii = 2.60 Å, C31⋯O1ii = 3.429(2) Å with angle at H31a = 141°]. The links between layers along the c-axis to consolidate the three-dimensional molecular packing are of the type hydroxyphenyl- and methylene-C—H⋯Cl [C4—H4⋯Cl1iv: H4⋯Cl1iv = 2.81 Å, C4⋯Cl1iv = 3.5952(17) Å with angle at H4 = 141° and C15—H15b⋯Cl2v: H15b⋯Cl2v = 2.73 Å, C15⋯Cl2v 3.699(2) Å with angle at H15b = 166° for (iv) x, 1/2 − y, 1/2 + z and (v) −1/2 + x, 1/2 − y, 1 − z].

Finally, an analysis of the calculated Hirshfeld surfaces was conducted. This was accomplished employing Crystal Explorer 17 [13] and literature procedures [14], including the calculation of the full and decomposed two-dimensional fingerprint plots. In particular, a recent study showed how such an analysis can be employed to differentiate between multiple molecules in the asymmetric unit [15]. The most prominent contacts on the Hirshfeld surface for each individual molecule are, not surprisingly, H⋯H contacts and the percentage contributions for the Cl1–Cl3-molecules, i.e. 38.5, 31.5 and 32.6%, differentiate between the Cl1-molecule on the one hand and the Cl2- and Cl3-molecules on the other. A similar differentiation is seen in the C⋯H/H⋯C contacts of 20.3, 26.7 and 25.6%, respectively. To a first approximation, the percentage contributions from the O⋯H/H⋯O [16.6, 17.0 and 17.5%] and Cl⋯H/H⋯Cl [15.6, 13.4 and 12.8%] contacts are about the same. The 3.6, 1.7 and 3.8% contributions from the C⋯C contacts and 1.1, 1.9 and 1.2% from the O⋯C/C⋯O contacts highlight small differences between the molecules.

Acknowledgements

Sunway University Sdn Bhd is thanked for financial support of this work through Grant no. STR-RCTR-RCCM-001-2019.

References

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Received: 2019-07-25
Accepted: 2019-08-12
Published Online: 2019-09-10
Published in Print: 2019-11-26

©2019 See Mun Lee et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
https://doi.org/10.1515/ncrs-2019-0528
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Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
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