Startseite Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
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Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2

  • Sang Loon Tan und Edward R.T. Tiekink ORCID logo EMAIL logo
Veröffentlicht/Copyright: 21. 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

C35H25BrO10S4, triclinic, P1̄ (no. 2), a = 7.9533(2) Å, b = 10.27180(10) Å, c = 20.6598(4) Å, α = 103.462(1)°, β = 95.933(2)°, γ = 96.008(1)°, V = 1618.11(5) Å3, Z = 2, Rgt(F) = 0.0624, wRref(F2) = 0.1759, T = 100(2) K.

CCDC no.: 1953253

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:Colourless prism
Size:0.09 × 0.06 × 0.05 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:4.68 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:76.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:41307, 6729, 0.041
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 6431
N(param)refined:466
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Br11.00883(7)0.79638(5)0.31164(3)0.03747(17)
S10.78070(11)0.40858(9)0.26241(4)0.01657(19)
S20.81477(12)0.50631(8)0.36235(4)0.0170(2)
S30.53249(12)0.89453(8)0.74523(4)0.0186(2)
S40.56038(12)1.00647(9)0.84254(4)0.0184(2)
O10.7024(5)0.5139(4)0.00345(18)0.0443(9)
O20.5582(5)0.5877(4)0.08759(19)0.0389(8)
H2O0.477(10)0.554(7)0.060(4)0.058*
O30.7131(3)0.3124(3)0.12900(13)0.0182(5)
O40.9000(4)0.2621(3)0.05612(13)0.0223(6)
H4O0.810(4)0.229(5)0.030(2)0.033*
O50.7635(4)0.6292(3)0.48742(13)0.0197(5)
O60.6687(4)0.5222(3)0.56240(13)0.0204(5)
H6O0.646(7)0.600(2)0.579(3)0.031*
O70.5956(4)0.7640(3)0.62061(13)0.0218(6)
O80.6849(4)0.8689(3)0.54466(14)0.0242(6)
H8O0.711(7)0.793(3)0.527(3)0.036*
O90.6224(3)1.1430(3)0.97132(13)0.0221(6)
O100.4344(4)1.2113(3)1.04050(14)0.0250(6)
H10O0.520(5)1.236(6)1.070(2)0.038*
C10.6985(6)0.5727(4)0.0625(2)0.0311(9)
C20.8582(6)0.6280(4)0.1091(2)0.0284(9)
C30.8523(6)0.6768(4)0.1773(2)0.0266(8)
H30.74710.67620.19530.032*
C41.0049(6)0.7261(4)0.2178(2)0.0289(9)
C51.1596(6)0.7260(5)0.1935(3)0.0371(11)
H51.26340.75830.22270.045*
C61.1593(7)0.6770(5)0.1244(3)0.0408(11)
H61.26460.67710.10640.049*
C71.0125(7)0.6296(5)0.0827(3)0.0349(10)
H71.01420.59760.03580.042*
C80.8611(5)0.3092(3)0.11679(17)0.0150(7)
C91.0095(5)0.3574(3)0.16954(17)0.0149(7)
C101.1742(5)0.3543(4)0.15098(19)0.0188(7)
H101.18750.32490.10490.023*
C111.3176(5)0.3933(4)0.1986(2)0.0221(8)
H111.42850.39090.18550.027*
C121.2966(5)0.4360(4)0.2659(2)0.0208(7)
H121.39410.46130.29910.025*
C131.1350(5)0.4420(4)0.28533(18)0.0193(7)
H131.12340.47260.33150.023*
C140.9891(5)0.4038(3)0.23784(18)0.0170(7)
C150.8289(5)0.3753(4)0.40607(18)0.0170(7)
C160.8785(5)0.2520(4)0.37535(19)0.0196(7)
H160.90710.23750.33090.023*
C170.8864(5)0.1499(4)0.4093(2)0.0236(8)
H170.91830.06580.38740.028*
C180.8485(5)0.1695(4)0.4743(2)0.0236(8)
H180.85500.09980.49730.028*
C190.8005(5)0.2931(4)0.50569(19)0.0208(7)
H190.77440.30720.55040.025*
C200.7904(5)0.3960(3)0.47256(18)0.0162(7)
C210.7398(5)0.5266(4)0.50773(17)0.0170(7)
C220.6129(5)0.8653(4)0.59878(17)0.0170(7)
C230.5550(5)0.9938(4)0.63122(19)0.0186(7)
C240.5407(5)1.0916(4)0.59543(19)0.0229(8)
H240.57151.07560.55130.027*
C250.4821(6)1.2127(4)0.6229(2)0.0270(9)
H250.47581.28000.59840.032*
C260.4336(6)1.2337(4)0.6860(2)0.0285(9)
H260.39051.31500.70470.034*
C270.4469(6)1.1369(4)0.7228(2)0.0257(8)
H270.41291.15340.76640.031*
C280.5088(5)1.0165(4)0.69696(18)0.0193(7)
C290.3508(5)1.0177(3)0.86487(18)0.0172(7)
C300.2067(5)0.9649(4)0.81789(19)0.0191(7)
H300.22010.92360.77290.023*
C310.0434(5)0.9719(4)0.8360(2)0.0219(8)
H31−0.05310.93570.80320.026*
C320.0205(5)1.0311(4)0.9012(2)0.0233(8)
H32−0.09111.03360.91360.028*
C330.1622(5)1.0868(4)0.94836(19)0.0197(7)
H330.14701.12860.99310.024*
C340.3271(5)1.0823(3)0.93098(18)0.0153(7)
C350.4743(5)1.1469(3)0.98236(18)0.0159(7)

Source of material

The title 2:1 co-crystal was prepared through solvent drop grinding of 2-mercaptobenzoic acid (Merck, Darmstadt, Germany) (0.154 g, 1 mmol) and 3-bromobenzoic acid (Alfa Aesar, Heysham, Lancashire, United Kingdom) (0.201 g, 1 mmol) in a 1:1 molar ratio. The mixture was ground for 15 mins in the presence of a few drops of methanol and the process was repeated three times. Upon dissolving the mixture in dimethylformamide (1 mL), the solution was then carefully layered with benzene (1.5 mL). Colourless crystals formed after two weeks. M.pt: 491–493 K. IR (ATR, cm−1): 3066–2829(w) ν(C—H), 1683(s) ν(C=O), 1560(m) ν(C=C), 1415(m) δ(C—H), 739(s) δ(C=C), 669(m) ν(C—Br), 493(w) ν(S—S).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The O-bound H-atoms were located in a difference Fourier map but were refined with a distance restraint O—H = 0.84 ± 0.01 Å, and with Uiso(H) set to 1.5Ueq(O). Owing to poor agreement, one reflection, i.e. (0 −1 1), was omitted from the final cycles of refinement.

Comment

In continuation of a long-held interest in co-crystals of 2-[(2-carboxyphenyl)disulfanyl]benzoic acid (2,2′-dithiodibenzoic acid; DTBA) [5], [6], recent attention has been directed to co-crystal formation of this conformationally flexible di-acid [7] with benzoic acid derivatives. Thus, it has been possible to isolate the anticipated 1:2 co-crystal, DTBA.2 (benzoic acid) whereby each carboxylic acid group of DTBA associated with benzoic acid via a non-symmetric, eight-membered {⋯HOCO}2 synthon [8]. However, analogous experiments with 3-chlorobenzoic acid (3-ClBA) gave rise to an unexpected 1:1:1 multi-component crystal comprising DTBA, 3-ClBA and dimethylformamide (DMF) [9]. Here, one carboxylic acid associated with 3-ClBA via the {⋯HOCO}2 synthon but the second residue formed a seven-membered {⋯HOCO⋯HCO} heterosynthon with the DMF molecule [9]. This species was isolated from the recrystallisation of a thoroughly ground powder (solvent drop method with methanol) comprising a 1:1 mixture of 2-mercaptobenzoic acid and 3-ClBA in toluene which was layered with DMF; co-crystallisation experiments with 2-mercaptobenzoic acid are well-known to produce DTBA [5], [6], [10] and, indeed, other side-products [11]. A similar experiment in which the powder was crystallised from dichloromethane layered with benzene gave the 2:1 co-crystal 2DTBA.3-ClBA [12]. In the present report, analogous experiments were conducted but with 3-bromobenzoic acid (3-BrBA) as the co-former. After recrystallisation from dimethylformamide layered with benzene, the non-solvated 2:1 co-crystal 2DTBA.3-BrBA was isolated, the crystal and molecular structures of which are reported herein.

As illustrated in the figure (50% probability displacement ellipsoids), the X-ray crystallographic analysis showed the asymmetric unit in the title 2:1 co-crystal to comprise two independent molecules of DTBA and one of 3-BrBA, consistent with oxidation of 2-MBA during co-crystal formation [5], [6], [10]. The 3-BrBA molecule exhibits a twist between the aromatic ring and the carboxylic acid residue with the dihedral angle between the planes being 8.38(3)°. The DTBA molecules are twisted as seen in the values of the C14—S1—S2—C15 and C28—S3—S4—C29 torsion angles of −90.73(19) and 86.79(19)°, respectively. This is also reflected in the dihedral angles between the (C9—C14) and (C15—C20) rings of 79.3(13)°, and between the (C23—C28) and (C29—C34) rings of 80.85(13)°. Variable twists between the O3-, O5-, O7- and O9-carboxylic acid groups and the phenyl rings to which they are attached are evident as seen in the sequence of C6/CO2 dihedral angles of 3.89(12), 15.6(4), 14.5(5) and 5.1(3)°, respectively. A least-squares fit calculation [13] comparing the independent DTBA molecules show the r.m.s. deviation of distances and angles to be 0.0051 Å and 0.483°, respectively, consistent with a high degree of concordance between the DTBA molecules.

In the molecular packing, and as shown in the figure, the DTBA molecules associate via hydroxy-O—H⋯O(carbonyl) hydrogen bonding and an eight-membered {⋯HOCO}2 synthon [O6—H6o⋯O7: H6o⋯O7 = 1.81(4) Å, O6⋯O7 = 2.648(4) Å with angle at H6o = 176(7)° and O8—H8o⋯O5: H8o⋯O5 = 1.80(4) Å, O8⋯O5 = 2.640(4) Å with angle at H8o = 179(7)°]. The remaining carboxylic acid residues of the DTBA molecules associate with symmetry-related DTBA molecules via hydroxy-O—H⋯O(carbonyl) hydrogen bonds [O4—H4o⋯O9i: H4o⋯O9i = 1.82(4) Å, O4⋯O9i = 2.660(4) Å with angle at H4o = 175(5)° and O10—H10o⋯O3ii: H10o⋯O3ii = 1.84(4) Å, O10⋯O3ii = 2.670(4) Å with angle at H10o = 171(5)° for symmetry operations (i) x, −1 + y, −1 + z and (ii) x, 1 + y, 1 + z]. The result of the aforementioned mode of association is a linear supramolecular chain along [0 1 1]. The 3-BrBA molecules self-associate about a centre of inversion via hydroxy-O—H⋯O(carbonyl) hydrogen bonds to form a dimeric aggregate [O2—H2o⋯O1iii: H2o⋯O1iii = 1.79(8) Å, O2⋯O1iii = 2.598(5) Å with angle at 177(10)° for (iii) 1 − x, 1 − y, −z]. Neighbouring supramolecular chains are connected by dimeric aggregates formed by the 3-BrBA molecules via side-on C—Br⋯π interactions [C4—Br1⋯Cg(C23—C28)iv: Br1⋯Cg(C23—C28)iv = 3.9117(19) Å, C4⋯Cg(C23—C28)iv = 4.427(5) Å with angle at Br1 = 92.64(15)° for (iv) 2 − x, 2 − y, 1 − z]. In a similar fashion, centrosymmetrically-related supramolecular chains are connected directly via side-on C=O⋯π interactions [C21—O5⋯Cg(C15—C20)v: O5⋯Cg(C15—C20)v = 3.300(3) Å, C21⋯Cg(C15—C20)v = 3.662(4) Å with angle at O5 = 97.2(2)° for (v) 1 − x, 1 − y, 1 − z]. In addition, π—π stacking interactions link 3-BrBA and DTBA rings to consolidate the three-dimensional architecture [Cg(C9—C14)⋯Cg(C2—C7) = 3.706(3) Å and angle of inclination = 6.0(2)° and Cg(C29—C34)⋯Cg(C2—C7)vi = 3.729(3) Å and angle of inclination = 7.0(2)° for (vi) 1 − x, 2 − y, 1 − z].

Further insight into the supramolecular association in the title co-crystal and the isostructural 3-ClBA species [12] was gained through an analysis of the calculated Hirshfeld surfaces as well as the full and delineated two-dimensional fingerprint plots using literature procedures [14] and Crystal Explorer 17 [15]. The calculations were performed on the asymmetric unit illustrated in the figure, and for the entire asymmetric unit for the isostructural literature analogue [12]. This analysis reveals that a considerable number of different contacts impact upon the Hirshfeld surface with the most prominent contacts being H⋯H [30.8%], O⋯H/H⋯O [22.9%], C⋯H/H⋯C [12.8%] and S⋯H/H⋯S [10.0%]. Less prominent but significant contacts are of the type C⋯C [6.7%], O⋯C/C⋯O [6.4%] and Br⋯H/H⋯Br [5.0%]. The results of the analogous analysis of the molecular packing of the isostructural 3-ClBA species [12] mirror those of the title compound very closely. Thus, the greatest disparities are noted in the H⋯H [30.3%] and O⋯H/H⋯O [23.6%] percentage contibutions but, the differences are <1%; the differences in the other percentage contacts were 0.1% or less. These results emphasise the isostructural relationship in the two co-crystals.

Acknowledgements

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

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Received: 2019-07-11
Accepted: 2019-09-12
Published Online: 2019-09-21
Published in Print: 2019-11-26

©2019 Sang Loon Tan 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-2019-0489
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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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