Home Physical Sciences Crystal structure of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl) terephthalic acid-dimethylsulfoxide (1/1), C18H15N3O6 ⋅ C2H6OS
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Crystal structure of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl) terephthalic acid-dimethylsulfoxide (1/1), C18H15N3O6 ⋅ C2H6OS

  • Gunay Z. Mammadova , Iván Brito EMAIL logo and Alejandro Cárdenas
Published/Copyright: September 27, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 1

Abstract

C18H15N3O6 ⋅ C2H6OS, P21/c (no. 14), a = 15.762(9) Å, v = 6.013(4) Å, c = 22.264(11) Å, β = 103.522(19)°, V = 2052(2) Å3, Z = 4, Rgt(F) = 0.0484, wRref(F2) = 0.1348, T = 296(2) K.

CCDC no.: 1865971

The asymmeric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow plate
Size:0.16 × 0.13 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.21 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:25.6°, >99%
N(hkl)measured, N(hkl)unique, Rint:24106, 3810, 0.082
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2387
N(param)refined:283
Programs:Bruker [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
S10.16958(6)0.59889(12)0.58433(3)0.0497(2)
O10.17080(15)0.1222(3)0.51448(9)0.0564(6)
H1O0.1710570.0250210.5422640.085*
O20.07960(16)−0.1156(4)0.45720(10)0.0678(7)
O30.12752(13)0.4501(3)0.19721(8)0.0500(5)
H3O0.1318100.5376520.1680890.075*
O40.14698(15)0.7723(3)0.24669(8)0.0537(6)
O50.28494(13)1.0473(3)0.32101(9)0.0474(5)
O60.41696(16)1.1628(4)0.50389(9)0.0717(7)
O70.17262(15)0.8413(3)0.60476(8)0.0574(6)
N10.22718(14)0.7114(3)0.36826(9)0.0356(5)
H1N0.2284210.7952820.3349980.043*
N20.27689(14)0.7683(3)0.42174(9)0.0360(5)
N30.38148(15)1.2718(4)0.38409(10)0.0437(6)
H3N0.4065491.2848420.4246170.052*
C10.17745(16)0.5170(4)0.36289(11)0.0330(6)
C20.13361(16)0.4438(4)0.30374(11)0.0350(6)
C30.08753(17)0.2463(4)0.29796(13)0.0406(7)
H3A0.0589760.1962530.2589490.049*
C40.08340(18)0.1229(4)0.34923(12)0.0400(7)
H4A0.051529−0.0086850.3447400.048*
C50.12660(17)0.1942(4)0.40753(12)0.0358(6)
C60.17394(17)0.3903(4)0.41447(12)0.0363(6)
H6A0.2033560.4372100.4536060.044*
C70.32522(16)0.9480(4)0.42659(12)0.0364(6)
C80.32830(17)1.0927(4)0.37279(12)0.0367(6)
C90.39780(17)1.4298(4)0.34107(12)0.0394(6)
C100.45815(19)1.5942(5)0.36409(14)0.0486(7)
H10A0.4859771.5967940.4058130.058*
C110.4766(2)1.7534(5)0.32477(16)0.0566(8)
H11A0.5178461.8621670.3402060.068*
C120.4356(2)1.7556(5)0.26347(16)0.0564(8)
H12A0.4485341.8650530.2374730.068*
C130.3753(2)1.5947(5)0.24091(14)0.0507(8)
H13A0.3466661.5959060.1993420.061*
C140.35629(19)1.4303(5)0.27910(13)0.0457(7)
H14A0.3157511.3203780.2631660.055*
C150.13728(17)0.5748(5)0.24744(12)0.0382(6)
C160.12196(19)0.0521(5)0.46152(13)0.0432(7)
C170.37487(19)0.9915(5)0.49014(13)0.0498(8)
C180.3744(2)0.8217(6)0.53924(14)0.0684(10)
H18A0.4248020.8420140.5725810.103*
H18B0.3754950.6753540.5222290.103*
H18C0.3225310.8389620.5544040.103*
C190.0702(2)0.4970(6)0.59526(18)0.0715(10)
H19A0.0229070.5698610.5671480.107*
H19B0.0663210.5255330.6369560.107*
H19C0.0669430.3397050.5876750.107*
C200.2413(2)0.4575(5)0.64531(15)0.0623(9)
H20A0.2998850.5082230.6483650.093*
H20B0.2380910.3004840.6372500.093*
H20C0.2248030.4869240.6834100.093*

Source of material

(Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl) terephthalic acid was synthesized by aqueous diazotization of 2-aminoterephthalic acid with subsequent coupling with 3-oxo-N-phenylbutanamide [3, 4] .

Diazotization: A 10 mmol portion of 2-aminoterephthalic acid was dissolved in 50 mL of water upon addition of 0.80 g of Solid NaOH. The solution was cooled in an ice bath to 0 °C and 10 mmol of NaNO2 were added with subsequent addition of 2 mL 33% HCl in portions of 0.4 mL for 1 h, under vigorous stirring. During the reaction, the temperature of the mixture must not exceed +5 °C. The obtained diazonium salt was used for the next stage (see below).

Azocoupling: 10 mmol of NaOH were added to a mixture of 10 mmol of 3-oxo-N-phenylbutanamide in 50 mL ethanol. The solution was cooled in an ice bath, and a suspension of the diazonium salt (prepared according to the procedure described above) was added in two equal portions under rigorous stirring for 1 h. The formed yellow precipitate of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl)terephthalic acid was filtered off, recrystallized from a mixture methanol-dimethylsulfoxide (50:1, v/v) and dried in air. Yield 84% (based on 3-oxo-N-phenylbutanamide), yellow powder, soluble in DMSO, ethanol and dimethylformamide and insoluble in non-polar solvents. The formed yellow precipitate of the title was filtered off, recrystallized from a mixture methanol-dimethylsulfoxide (50:1, v/v) and dried in air. Anal. Calcd. for C20H21N3O7S (M = 447.46): C, 53.69; H, 4.73; N, 9.39. Found: C, 53.58; H, 4.70; N, 9.36%. IR (KBr): 3441 (br.) ν(H2O), 2498 ν(NH), 1664 ν(C=O), 1600 ν(C=N) cm−1. MS (ESI) (positive ion mode): m/z: 370.10 [M–DMSO + H]+ and 79.10 [DMSO + H]+. 1H NMR (DMSO-d6): δ 2.44 (s, 3H, CH3), 2.50 (s, 6H, 2CH3 signals of DMSO overlapped with the solvent peak), 7.25–8.40 (8H, Ar—H), 12.85 and 13.11 (s, 2H, OH), 16.00 (s, 1H, NH). 13C{1H} (DMSO-d6): δ 26.33 (CH3), 39.52 (signals of DMSO overlapped with the solvent peak), 115.69 (Ar—H), 116.44 (Ar—H), 120.73 (2Ar—H), 124.13 (Ar—H), 124.94 (Ar—H), 129.41 (2Ar—H), 131.15 (Ar—COOH), 131.79 (Ar—COOH), 135.23 (C=N), 137.89 (Ar—CNH), 143.93 (Ar—NH—N), 161.18 and 166.44 (—COOH), 168.89 and 199.47 (C=O).

Experimental details

H atoms were located in the difference Fourier map, but refined with fixed individual displacement parameters, using riding models with C—H distances of 0.93 Å (for aromatic rings), N—H distances of 0.90 Å; O—H distances of 0.85 Å and C—H distances 0.96 for methyl group with U(H) values of 1.2 Ueq (C,N,O) and 1.5 Ueq(C) (for CH3).

Comment

No covalent interactions have been extensively used as a synthetic tool in the synthesis, catalysis and design of materials [5], [6], [7], [8], [9], [10], [11], [12], [13], [14]. “σ-hole” directed bonding interactions, such as halogen bonding, chalcogen bonding, pnicogen bonding and tetrel bonding, plays a crucial role in controlling the molecular arrangement and further properties of crystal materials due to its moderate strength, directionality and tunability [10], [11], [14], [15], [16], [17], [18], [19], [20], [21].

In the title structure, the organic hydrazine molecule is essentially planar, (r.m.s. deviation = 0.174 Å) with a maximum deviation of 0.646(2) and −0.491(2) Å for the O3 and O4 atoms. All carbonyl groups O atoms are involved in intramolecular hydrogen bond interactions to hydrogen atoms of amino and phenyl groups, giving a S(6) motif in each case (cf. the figure) [22]. Both hydroxyl groups H atoms are involved in intermolecular hydrogen bond interactions to O atoms of dimethyl sulfoxide molecules linking the molecules into chains with graph-set notation C(13) along the [001] direction [22]. The bond lengths and angles are in the expected ranges.

Acknowledgements

IB thanks to Fondequip (EQM13–0021). G⋅Z⋅M⋅ thanks Baku State University.

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Received: 2018-06-20
Accepted: 2018-09-05
Published Online: 2018-09-27
Published in Print: 2018-12-19

©2018 Gunay Z. Mammadova et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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  38. Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN
  39. Crystal structure of N-(4-methoxybenzyl)pyridazin-3-amine- a rare Z′ = 4 structure, C12H13N3O
  40. Crystal structure of bis(perchlorato-κ1O)-bis(3,4,5-trimethoxy-N-(pyridin-2-yl)benzamide-κ2N,O)copper(II), C32H30Cl2CuN4O16
  41. Crystal structure of methyl 4-methyl-2,5-di(pyridin-4-yl)-1H-pyrrole-3-carboxylate monohydrate C17H15N3O2⋅H2O
  42. Crystal structure of dimethyl 5-(10-(methoxycarbonyl)anthracen-9-yl) isophthalate,C26H20O6
  43. Crystal structure of tert-butyl (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)carbamate, C16H24N2O4
  44. Crystal structure of aqua-bis(1,5-dimethyl-2-phenyl-4-(((E)-4-pyridylmethylene)amino)pyrazolidin-3-one-κN)-(nitrato-κO)-(nitrato-κ2O,O′)zinc(II), C34H34N10O9Zn
  45. Crystal structure of catena-poly[dichlorido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)cobalt(II)] – methanol (1/1), C18H20Cl2CoN4O2
  46. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)]bis(2-carboxybenzoate) dihydrate, MnC40H40N10O12
  47. The crystal structure of 4-((3,4-dichlorobenzylidene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, C18H15Cl2N3O
  48. Crystal structure of bis(2-methoxy-6-((2-(pyrimidin-2-yl)hydrazono)methyl)phenolato-κ3N,N′,O)iron(III) perchlorate, C24H22N8O8ClFe
  49. The crystal structure of 2-[4-hydroxy-3-methoxyphenyl]-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl, C14H19N2O4
  50. Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6
  51. Crystal structure of dichloro-tetrakis[(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol-κN]cadmium (II), C60H74CdCl6N12O4
  52. Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
  53. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
  54. The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
  55. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(tri(p-tolyl)phosphine-κP)copper(I) tetrafluoroborate – 4,4′-bipyridine (2/1), C57H54BCuF4N3P2
  56. The crystal structure of 2,6-dimethyl-3,5-dinitrocyclohexa-2,5-diene-1,4-dione, C8H6N2O6
  57. The crystal structure of 2,3-dimethyl-1,4-dinitrobenzene – a Z′ = 4 structure, C8H8N2O4
  58. Crystal structure of [(1,2-η)-1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl] (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-κ6N2,O4) rubidium (I), [Rb(diaza-18-crown-6)]Cp*, C22H41N2O4Rb
  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
https://doi.org/10.1515/ncrs-2018-0190
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of bis(6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2,4-diiodophenolato)-κ4N,N′,O,O′)cer(IV), C32H20CeI8N4O4
  3. Crystal structure of (6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato-κ2N,O))copper(II), C16H12Cl2CuN2O2
  4. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)samarium(III)], C26H18N2O9Sm
  5. Crystal structure of 1-{4-[(2-hydroxy-5-nitrobenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15N3O4
  6. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis(μ2-1-(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)trizinc(II), C44H38Zn3N4O12
  7. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)–bis(μ2–(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)tricobalt(II), C44H38Co3N4O12
  8. Crystal structure of poly[aqua(μ4-2,2′,2′′-nitrilotriacetato-κ6O1,O3,O5:O2:O4:O6)-yttrium(III)], C6H8NO7Y
  9. Crystal structure of catena-poly[bromido-(μ2-pyrazine-2-carboxylato-κ3N:N′,O)copper(II)], C10H6N4Cu2O4Br
  10. Crystal structure of poly[dodekais(μ2-2,6-difluorobenzoato-κ2O:O′)-bis((μ3-hexamethylenetetramine-κ3N:N′:N′′)hexacopper(II)], C48H30N4O12F12Cu3
  11. Crystal structure of methyl 4-(4-hydroxy-3-nitrophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H18N2O6
  12. Crystal structure of N-phenyl-2-(propan-2-ylidene)hydrazine-1-carbothioamide, C10H13N3S
  13. Crystal structure of sodium caesium zinc phosphate, NaCsZnP2O7
  14. Crystal structure of methyl 4-(4-isopropylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C23H29NO3
  15. Crystal structure of catena-poly[bis(μ2-1,3-di(4H-1,2,4-triazol-4-yl)benzene-κ2N:N′)-bis(thiocyanato-κ1N)cobalt(II), C22H16CoN14S2
  16. Crystal structure of catena-poly[(μ2-2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ2N:N′)-bis(2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ1N)-bis(thiocyanato-κ1N)cobalt(II)], C38H24CoN14S5
  17. Crystal structure of bis(2,5-di(pyridin-2-yl)-1,3,4-thiadiazole-κ2N,N′)-bis(thiocyanato-κ1N)cobalt(II), C26H16CoN10S4
  18. Crystal structure of (bis((1H-benzo[d]imidazol2-yl)methyl)amine-κ3N,N′,N′′)-(pyridine-2,6-dicarboxylato-κ3N,O,O′)zinc(II) — methanol — water (1/2/1), C25H28N6O7Zn
  19. Crystal structure of catena-poly[triaqua-(μ2-5-methoxy-isophthalato-κ2O:O′)copper(II)], C9H12CuO8
  20. Structure and photochromism of 1-[2-methyl-5-phenyl-3-thienyl]-2-[2-methyl-5-(4-chlorophenyl)-3-thienyl]3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16ClF6S2
  21. Crystal structure of methyl 4-(3-phenoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C26H27NO4
  22. Crystal structure of poly[diaqua-di-μ2-hydroxido-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ4O:O′:O′′:O′′′)-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ5O,O:O′:O′′:O′′′)disamarium(III)] – bipyridine (2/1), C21H11NF16O12Sm2
  23. Crystal structural of diethyl 4-(3,5-dibromo-4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C19H21Br2NO5
  24. Crystal structure of catena-poly[tetraaqua(μ2-4-(1H-imidazol-1-yl)pyridine-κ2N:N′))zinc(II)] thiophene-2,5-dicarboxylate, C14H17N3O8ZnS
  25. Crystal structure of (20S)-20-(dimethylamino)-3-(tigloylamino)-5α-pregn-2,16-dien-4-one, C28H42N2O2
  26. Crystal structure of rac-trans-N,N′-bis(3,5-diiodosalicylidene)-1,2-cyclohexanediamine, C20H18I4N2O2
  27. Crystal structure of 2-bromo-7-(4-(dimethylamino)phenyl)-10-methylacridin-9 (10H)-one, C22H19BrN2O
  28. Crystal structure of catena-poly[(μ2-pentane-1,5-dicarboxylato-κ2O:O′)-(μ2-2-[(1H-imidazol-1-yl)methyl]-6-methyl-1H-benzimidazole-κ2N:N′)zinc(II)] sesquihydrate, C17H21N4O5.5Zn
  29. Crystal structure of ethyl 2-amino-4-(3,4-difluorophenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C21H15F2NO5
  30. Crystal structure of 9-(5-methylthiophen-2-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione, C18H18O3S
  31. Crystal structure of [5,5′-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-2-ylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′]nickel(II), C23H30N4O4Ni
  32. Crystal structure of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl) terephthalic acid-dimethylsulfoxide (1/1), C18H15N3O6 ⋅ C2H6OS
  33. Crystal structure of (2E,4Z)-dimethyl 4-((phenylamino)methylene)pent-2-enedioate, C14H15N1O4
  34. Crystal structure of (2Z,2′Z)-1,1′-(pyridine-2,6-diyl) bis(3-hydroxy-3-phenylprop-2-en-1-one), C23H17NO4
  35. Crystal structure of ethyl 2-amino-4-(3-bromophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C21H16BrNO5
  36. Crystal structure of bis(μ2-3,5-dichloro-2-oxidobenzoato-κ4O,O′:O′,O′′)-hexakis(μ2-pivalato-κ2O:O′)-bis(pivalato-κ2O,O′)-tetrakis(1,10-phenanthroline-κ2N,N′)tetragadolinium(III), C102H108Cl4Gd4N8O22
  37. Crystal structure of catena-poly[aqua-bis(formato-κ1O)-(μ2-1,1′-(oxybis(1,4-phenylene))-bis(1H-1,2,4-triazole)-κ2N:N′)copper(II)]hydrate, C18H16CuN6O6
  38. Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN
  39. Crystal structure of N-(4-methoxybenzyl)pyridazin-3-amine- a rare Z′ = 4 structure, C12H13N3O
  40. Crystal structure of bis(perchlorato-κ1O)-bis(3,4,5-trimethoxy-N-(pyridin-2-yl)benzamide-κ2N,O)copper(II), C32H30Cl2CuN4O16
  41. Crystal structure of methyl 4-methyl-2,5-di(pyridin-4-yl)-1H-pyrrole-3-carboxylate monohydrate C17H15N3O2⋅H2O
  42. Crystal structure of dimethyl 5-(10-(methoxycarbonyl)anthracen-9-yl) isophthalate,C26H20O6
  43. Crystal structure of tert-butyl (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)carbamate, C16H24N2O4
  44. Crystal structure of aqua-bis(1,5-dimethyl-2-phenyl-4-(((E)-4-pyridylmethylene)amino)pyrazolidin-3-one-κN)-(nitrato-κO)-(nitrato-κ2O,O′)zinc(II), C34H34N10O9Zn
  45. Crystal structure of catena-poly[dichlorido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)cobalt(II)] – methanol (1/1), C18H20Cl2CoN4O2
  46. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)]bis(2-carboxybenzoate) dihydrate, MnC40H40N10O12
  47. The crystal structure of 4-((3,4-dichlorobenzylidene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, C18H15Cl2N3O
  48. Crystal structure of bis(2-methoxy-6-((2-(pyrimidin-2-yl)hydrazono)methyl)phenolato-κ3N,N′,O)iron(III) perchlorate, C24H22N8O8ClFe
  49. The crystal structure of 2-[4-hydroxy-3-methoxyphenyl]-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl, C14H19N2O4
  50. Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6
  51. Crystal structure of dichloro-tetrakis[(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol-κN]cadmium (II), C60H74CdCl6N12O4
  52. Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
  53. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
  54. The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
  55. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(tri(p-tolyl)phosphine-κP)copper(I) tetrafluoroborate – 4,4′-bipyridine (2/1), C57H54BCuF4N3P2
  56. The crystal structure of 2,6-dimethyl-3,5-dinitrocyclohexa-2,5-diene-1,4-dione, C8H6N2O6
  57. The crystal structure of 2,3-dimethyl-1,4-dinitrobenzene – a Z′ = 4 structure, C8H8N2O4
  58. Crystal structure of [(1,2-η)-1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl] (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-κ6N2,O4) rubidium (I), [Rb(diaza-18-crown-6)]Cp*, C22H41N2O4Rb
  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
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