Home Crystal structure of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate - ethanol (1/1), C19H28N6O7S
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Crystal structure of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate - ethanol (1/1), C19H28N6O7S

  • Binli Jiang ORCID logo and Guo-Chun Zhou EMAIL logo
Published/Copyright: October 25, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 2

Abstract

C19H28N6O7S, monoclinic, P21 (no. 4), a = 8.1573(1) Å, b = 17.4823(1) Å, c = 9.1162(1) Å, β = 116.432(1)°, V = 1164.14(2) Å3, Z = 2, Rgt(F) = 0.0273, wRref(F2) = 0.0732, T = 170(2) K.

CCDC no.: 1922467

The crystal 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:Block, colorless
Size:0.31 × 0.25 × 0.22 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:1.69 mm−1
Diffractometer, scan mode:XtaLAB Synergy R, ω-scans
θmax, completeness:75.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:21113, 4394, 0.019
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4350
N(param)refined:302
Programs:CrysAlisPRO [1], SHELX [2], [3], DIAMOND [4]
Table 2:

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

AtomxyzUiso*/Ueq
S10.85986(6)0.37651(3)0.28561(5)0.01876(12)
O1−0.3533(3)0.65911(14)0.2025(3)0.0560(6)
O2−0.1375(3)0.71613(14)0.4088(3)0.0587(6)
O30.4740(3)0.50527(11)−0.0885(2)0.0422(5)
O40.4055(2)0.38181(11)−0.09722(18)0.0349(4)
O50.7888(2)0.31740(9)0.3507(2)0.0295(4)
O61.0424(2)0.40402(9)0.38129(17)0.0259(3)
N1−0.1905(3)0.66482(12)0.3028(3)0.0348(5)
N2−0.0780(3)0.61244(11)0.2883(3)0.0285(4)
N30.1913(3)0.66470(11)0.5140(2)0.0260(4)
H3A0.3101830.6605620.5745240.031*
H3B0.1303770.7021120.5320390.031*
N40.1968(2)0.55826(11)0.3690(2)0.0260(4)
H40.1363620.5262890.2882890.031*
N50.7264(2)0.45014(10)0.2511(2)0.0177(3)
H50.7729610.4958320.2855170.021*
N60.9252(2)0.46816(11)0.0431(2)0.0210(4)
C10.1039(3)0.61466(13)0.3957(3)0.0222(4)
C20.3924(3)0.54635(15)0.4655(3)0.0282(5)
H2A0.4187710.5336800.5797160.034*
H2B0.4588110.5940000.4672020.034*
C30.4586(3)0.48193(14)0.3938(3)0.0254(5)
H3C0.3921530.4344500.3933060.030*
H3D0.5904480.4731060.4647810.030*
C40.4304(3)0.49857(14)0.2203(3)0.0245(4)
H4A0.4782110.5502160.2165720.029*
H4B0.2977410.4982260.1451880.029*
C50.5270(3)0.43976(12)0.1620(2)0.0204(4)
H5A0.4954510.3873210.1851750.024*
C60.4652(3)0.44737(12)−0.0218(2)0.0224(4)
C70.3542(5)0.3810(2)−0.2722(3)0.0489(7)
H7A0.2503330.415568−0.3291600.073*
H7B0.3195610.328988−0.3147190.073*
H7C0.4582390.398010−0.2902960.073*
C80.8428(3)0.34286(12)0.0965(2)0.0208(4)
C90.7882(3)0.26874(14)0.0494(3)0.0320(5)
H90.7583530.2359600.1171080.038*
C100.7769(4)0.24199(17)−0.1011(4)0.0435(6)
H100.7402430.190735−0.1340140.052*
C110.8181(4)0.28883(17)−0.1994(3)0.0405(6)
H110.8121470.269419−0.2989630.049*
C120.8694(3)0.36586(14)−0.1558(3)0.0277(5)
C130.9044(3)0.41828(17)−0.2564(3)0.0331(5)
H130.9017240.401232−0.3564230.040*
C140.9418(3)0.49288(16)−0.2117(3)0.0321(5)
C150.9493(3)0.51471(14)−0.0593(3)0.0262(5)
H150.9735430.566946−0.0285660.031*
C160.8826(3)0.39381(12)−0.0049(2)0.0203(4)
C170.9782(4)0.5516(2)−0.3143(3)0.0499(8)
H17A1.1061810.568157−0.2578810.075*
H17B0.8976570.595800−0.3314600.075*
H17C0.9542920.529222−0.4205090.075*
O70.5473(3)0.65204(13)0.8022(2)0.0552(6)
H70.5477950.6259400.8797710.083*
C180.6725(5)0.7570(2)0.7241(5)0.0571(9)
H18A0.5495940.7758870.6516620.086*
H18B0.7139030.7223150.6629880.086*
H18C0.7571690.8003280.7652710.086*
C190.6675(4)0.71484(18)0.8660(4)0.0485(7)
H19A0.7917000.6966630.9415590.058*
H19B0.6236750.7491520.9275020.058*

Source of materials

Procedures for preparation of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate was adapted from the reported paper [5], [6]. Sodium carbonate (3.64 g, 34.3 mmol) was added to a solution of methyl Nω′-nitro-L-argininate (4.00 g, 17.15 mmol) in water (40 mL) under stirring. The mixture was stirred for 1 hour at 0 °C. Then a solution of 3-methylquinoline-8-sulfonyl chloride (7.46 g, 30.87 mmol) in tetrahydrofuran (40 mL) was added and the mixture was warmed up to room temperature and stirred for 4 hours.

The crude residue was purified by flash column chromatography with an appropriate eluting solvent system. Off-white, Yield, 85%. 1H NMR (400 MHz, DMSO) δ 8.86 (d, J = 2.2 Hz, 1H), 8.27 (s, 1H), 8.21 (dd, J = 7.3, 1.3 Hz, 1H), 8.17 (dd, J = 8.3, 1.2 Hz, 1H), 7.90 (d, J = 8.5 Hz, 1H), 7.72–7.64 (m, 1H), 4.36– 4.26 (m, 1H), 3.18 (s, 3H), 3.11–2.99 (m, 2H), 2.53 (s, 3H), 1.72–1.33 (m, 5H), 1.23 (s, 2H). 13C NMR (101 MHz, CDCl3): δ 171.34, 159.25, 153.11, 141.17, 135.66, 135.52, 133.08, 132.36, 129.51, 128.66, 125.52, 55.71, 52.13, 40.35, 30.19, 24.33, 18.74. HR-MS(ESI+) m/z calcd. for C17H23N6O6S [M + H]+: 439.1400, Found: 439.1422 (M + H); IR (cm−1): 3408(w), 3295(w), 3250(w), 1737(s), 1623(s), 1596(s), 1538(w), 1418(m), 1331(m), 1253(s), 1221(m), 1160(s), 1138(m), 1008(w), 937(w), 886(w), 770(m), 679(m), 582(s), 536(m), 489(w).

The ethanol solvate was synthesized by the following procedure. An amount of 1 mmol methyl(E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate was dissolved in a mixed solvent of 5 mL absolute ethanol and 1 mL dichloromethane, then the solution was stayed in room temperature for slow evaporation. Colorless crystals were formed after three days. Yield: 80%.

Experimental details

The structure was solved with the ShelXT [2] structure solution program and refined with the XL [3] refinement package. The positions of the hydrogen atoms were generated geometrically. The figure was drawn by Diamond 4.0 [4].

Comment

The title compound is an important intermediate for the thrombin inhibitor argatroban. Argatroban was synthesized in 1970 [7]. The crystal structure of this intermediate is benefit to understand the reaction mechanism. Two related structures were found in the CSD: One is Nη-nitro-L-arginine methyl ester hydrochloride, and the other is L-nitroargininium picrate [8], [9].

The asymmetric unit contains one tite molecule and one ethanol. The bond lengths and angles within these moieties are in the expected ranges. The S1—N5 distance is 1.6237(17) Å. The C5—N5 distance is 1.470(3) Å. Viewing nitroguanidine part closer. For C—N bond, the distance of C1—N2, C1—N3, C1—N4 is 1.367(3) Å, 1.324(3) Å and 1.330(3) Å, respectively. For N—N bond, the distance of N1—N2 is 1.344(3) Å.

There are four intermolecular hydrogen bonds: N3—H3A⋯O7 (dN⋯O = 2.932(1) Å; ∠NHO = 153°, ′′ = 1 − x; +1/2 + y; 1 − z), N4—H4⋯N6 (dN⋯N = 3.218(1) Å; ∠NHN = 165°, ′′ = −1 + x; y; z), N5—H5⋯N2 (dN⋯N = 3.198(1) Å; ∠NHN = 157°, ′′ = 1 + x; y; z) and O7—H7⋯O3 (dO⋯O = 2.909(1) Å; ∠OHO = 136°, ′′ = 1 − x; −1/2 + y; −z). Intermolecular hydrogen bonds extend the structure to a three dimensional framework.

Acknowledgements

We gratefully acknowledge the financial support from Doctoral Scientific Research Foundation of Guangxi University of Chinese Medicine (XB017022) and Cultivating High-level Talent Teams in the Qi Huang Project of Guangxi University of Chinese Medicine, China (2018002). Xin-Ting Yan is supported by Undergraduate Student Scientific Research Training Project of Guangxi University of Chinese Medicine (2018DXS17).

References

1. Oxford Diffraction Ltd. CrysAlisPRO, Abingdon, Oxfordshire, England (2006).Search in Google Scholar

2. Sheldrick, G. M.: SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar

4. Brandenburg, K.: DIAMOND. Visual Crystal Structure Information System. Ver. 4.0. Crystal Impact, Bonn, Germany (2015).Search in Google Scholar

5. Cossy, J.; Belotti, D.: A short synthesis of argatroban: a potent selective thrombin inhibitor. Bioorg. Med. Chem. Lett. 11 (2001) 1989–1992.10.1016/S0960-894X(01)00351-1Search in Google Scholar

6. Alegret, C.; Santacana, F.; Riera, A.: Enantioselective synthesis of trans-4-methylpipecolic acid. J. Org. Chem. 72 (2007) 7688–7692.10.1021/jo071220zSearch in Google Scholar PubMed

7. Liu, K.; Kang, Y.; Li, J.; Zang, D.; Ma, D.: Synthesis of Argatroban. Chin. J. Pharm. 46 (2015) 1161–1164.Search in Google Scholar

8. Okabe, N.; Ikeda, K.; Kohyama, Y.: N′-Nitro-L-arginine methyl ester hydrochloride. Acta Crystallogr. C50 (1994) 2088–2089.10.1107/S0108270194004609Search in Google Scholar

9. Apreyan, R. A.; Fleck, M.; Atanesyan, A. K.; Sukiasyan, R. P.; Petrosyan, A.M.: L-Nitroargininium picrate. J. Mol. Struct. 1101 (2015) 236–242.10.1016/j.molstruc.2015.08.035Search in Google Scholar

Received: 2019-08-17
Accepted: 2019-10-08
Published Online: 2019-10-25
Published in Print: 2020-02-25

© 2019 Binli Jiang et al., published by De Gruyter, Berlin/Boston

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

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  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
https://doi.org/10.1515/ncrs-2019-0597
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Articles in the same Issue

  1. Frontmatter
  2. Synthesis and crystal structure of bis{5-fluorine-2-(((4-(1-(methoxy-imino)ethyl)phenyl) imino)methyl)phenolato-κ2N,O}copper(II), C32H28CuF2N4O4
  3. Redetermination of the crystal structure of N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide monohydrate, C16H17FN2O4
  4. The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C15H12ClFN2O2
  5. Crystal structure of (E)-N-[4-(1H)-imidazolyl phenyl]-(2-methylphenyl)methanimine, C17H15N3
  6. The crystal structure of 1-benzyl-4-(2-(phenylethynyl)phenyl)-1H-1,2,3-triazole, C23H17N3
  7. Crystal structure of catena-poly[{μ2-1,5-bis(diphenylphosphanyl)pentane-κ2P:P′}dichloridocadmium(II)], C29H30CdCl2P2
  8. Crystal structure of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate - ethanol (1/1), C19H28N6O7S
  9. The crystal structure of trans-carbonyl-(diphenylcyclohexyl-phosphine-κP)iodidomethyl-(2-oxopyridin-1(2H)-olato-κ2O,O′)rhodium(III), C25H28INO3PRh
  10. Crystal structure of N-(amino(pyrazin-2-yl)methylene)-6-methylpyridin-1-ium-3-carbohydrazonate-κ3O,N,N′)-(dinitrato-κ1O)zinc(II), C12H12N8O7Zn
  11. The crystal structure of dichlorido-(tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′)chromium(III) chloride — methanol (1/3), CrC27H33Cl3N7O3
  12. Crystal structure of catena-poly[aqua(μ4-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ8O,O′:O′,N:N′,O′′:O′′,O′′′))silver(I)], C10H24Ag2N2O10S2
  13. Crystal structure of bis(μ3-oxido)-bis(μ2–2,3,4,5-tetrafluorobenzoato-κ2O:O′)-bis(2,3,4,5-tetrafluorobenzoato-κO)-oktakis(3-chlorobenzyl-κC)tetratin(IV), C84H52Cl8F16O10Sn4
  14. Crystal structure of (E)-1-{4-[(4-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15FN2O2
  15. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-N,N′)zinc(II)], {C20H30N4O4P2S4Zn}n
  16. Crystal structure of methyl 2-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H12IN3O2
  17. Crystal structure of hexacarbonyl-(μ2-methanoato-k2O:O′)-(μ2–bis(di-p-tolylphosphino)cyclohexylamine-κ2P:P′)dirhenium(I), C42H45NO8P2Re2
  18. The cocrystal structure of 1′-hydroxy-1H,1′H-[5,5′-bitetrazol]-1-olate and 1,10-phenanthrolin-1-ium, C14H10N10O2
  19. The crystal structure of 1-benzyl-2-((4-(tert-butyl)phenyl)ethynyl)pyridin-1-ium bromide,C24H24BrN
  20. Crystal structure of (5,5′-bitetrazole-1,1′-diolate)-bis(1,10-phenanthroline)-copper(II), C26H16CuN12O2
  21. Crystal structure of bis(ammonium) diaqua-tetrakis(4-hydroxybenzoato)-manganese(II) tetrahydrate, [NH4]2[C28H24MnO14] ⋅ 4(H2O)
  22. The crystal structure of 3-chloro-1-hydrazino-2,4,6-trinitrobenzene, C6H4ClN5O6
  23. Crystal structure of catena-[(μ2-pyrazine-κ2N:N′)-bis(O,O′-di-ethyldithiophosphato-κ2S,S′)cadmium(II)], {C12H24CdN2O4P2S4}n
  24. Crystal structure of catena-poly[(μ2-pyrazine-N,N′)-bis(O,O′-di-isopropyldithiophosphato-S,S′)cadmium(II) acetonitrile di-solvate], [C16H32CdN2O4P2S4⋅2(C2H3N)]n
  25. Crystal structure of catena-poly{(μ2-N1,N2-bis[(pyridin-4-yl)methyl]ethanediamide-κ2N:N′)-bis(O,O′-di-isopropyldithiophosphato-κ1S)zinc(II)} — acetonitrile (1/1), C26H42N4O6P2S4Zn⋅C2H3N
  26. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)cobalt(II), C16H22O10Co
  27. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  28. Crystal structure of catena-poly[(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)-bis(O,O′-dimethyl dithiophosphato-κ2-S,S′)cadmium(II)], {C16H22CdN4O4P2S4}n
  29. Crystal structure of catena-poly[(bis(O,O′-diethyl dithiophosphato-κ2S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  30. The crystal structure of catena-poly[(E)-2-(((5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol], C12H15N3OS2Sn
  31. Crystal structure of dichlorido(N-o-tolyl-1,1-di-p-tolylphosphanamine–κ1P)-(methoxydi-p-tolylphosphane-κ1P)palladium(II), C36H39Cl2NOP2Pd
  32. The crystal structure of the triclinic polymorph of hexameric (trimethylsilyl)methyllithium, C24H66Li6Si6
  33. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′O)cobalt(III) 7,7,8,8-tetracyanoquinodimethane, C34H22CoN8O4
  34. Synthesis and crystal structure of benzyl 5-oxo-5-phenyl-2-(quinolin-2-yl)pentanoate, C27H23NO3
  35. Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 4-(2,2-dichloroacetyl)-3,4-dihydro-2 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5
  36. Crystal structure of dipentyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C18H28O6
  37. The crystal structure of catena-poly[diaqua-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)dicadmium(II)], C30H18Cd2N2O10S2
  38. Crystal structure of 2,7-diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine, C14H14B2F4I2N4
  39. A dinuclear Eu(III) complex in the crystal structure of dodecaaqua-bis(μ2-4-(1H-tetrazol-5-yl)benzoato-κ2O:O′) bis(5-(4-carboxylatophenyl)tetrazol-1-ide) tetrahydrate, C32H50Eu2N16O24
  40. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C24H18F2N2O3S
  41. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate (2/1/1), C53H50F2N6O10S2
  42. Crystal structure of 4-dimethylamino-pyridin-1-ium uracil-1-acetate, C13H16N4O4
  43. Crystal structure of dimethylammonium 5-fluorouracil-1-acetate, C8H12N3O4F
  44. Crystal structure of bis(N′-((5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioato-κ2N,O)nickel(II), C22H30N8O4S2Ni
  45. Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-((bis-pyrazol-1-yl)methane-κ2N,N′) rhodium(III) hexafluorophosphate. (C17H23ClN4RhF6P)
  46. The crystal structure of 5-(benzofuran-2-carbonyl)-N-cyclohexyl-5,6-dihydrophenanthridine-6-carboxamide, C29H26N2O3
  47. The crystal structure of 2-oxo-2H-chromen-4-yl acetate, C11H8O4
  48. The crystal structure of 2-nitroisophthalic acid, C8H5NO6
  49. Crystal structure of 3-fluoro-9-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino [2′,1′:1,6]pyrazino[2,3-b]quinoxaline, C19H17FN4O
  50. Crystal structure of (4-fluorobenzyl-κC)(bis(2-hydroxyethyl) carbamodithioato-κ2S,S′)(2,2′-imino-diethanolato-κ3N,O,O′)tin(IV), C16H25FN2O4S2Sn
  51. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-bromophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18BrF3N2O3S
  52. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18ClF3N2O3S
  53. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridomanganate(II), C10H16Cl4MnN2
  54. The crystal structure of 3-carboxy-5-methylpyridin-1-ium-2-carboxylate, C8H7NO4
  55. Crystal structure of bis(3-methoxy-N-(1-(pyridin-2-yl)ethylidene)benzohydrazonato κ3O,N,N′)zinc(II), C30H28N6O4Zn
  56. Crystal structure of dichlorido-(4,4′-dichloro-2,2′-bipyridine-κ2N,N′)platinum(II) — acetone (1/1), C13H12Cl4N2PtO
  57. Crystal structure of diethyl 6,12-bis(4-fluorophenyl)-2,10-dimethoxy-3,9-diphenyl-3,9-diazatetracyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C42H42F2N2O6
  58. Synthesis and crystal structure of (1E,3E)-2-hydroxy-5-methylisophthalaldehyde O,O-di(2-((((E)-(2-hydroxynaphthalen-1-yl)methylene)amino)oxy)ethyl) dioxime, C35H32N4O7
  59. The crystal structure of 2-phenyl-4,6-bis(prop-2-yn-1-yloxy)-1,3,5-triazine, C15H11N3O2
  60. Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3
  61. Crystal structure of bis-[N-(3-ethyl-1-pyrazin-2-yl-ethylidene)-3-bromo-benzoic acid-hydrazonato-κ3O,N,N′)]-cadmium(II), C30H28N8O2Br2Cd
  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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