Home Physical Sciences Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
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Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5

  • Fatin Nur Ain Abdul Rashid ORCID logo , Muhamad Zulfaqar Bacho , Alexandra M. Z. Slawin , Mohd Abdul Fatah Abdul Manan , Saiful Azmi Johari ORCID logo and Mohd Fazli Mohammat EMAIL logo
Published/Copyright: December 13, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 1

Abstract

C16H20N2O5, triclinic, P 1 ‾ (no. 2), a = 7.9179(7) Å, b = 10.1982(9) Å, c = 10.4144(8) Å, α = 76.184(7)°, β = 87.090 (7)°, γ = 73.500(8)°, V = 782.86(12) Å3, Z = 2, R gt (F) = 0.0458, wR ref (F 2) = 0.1333, T = 93 K.

CCDC no.: 2208835

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: 0.20 × 0.10 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: Rigaku XtaLAB P200, ω
θ max, completeness: 26.4°, >99%
N(hkl) measured, N(hkl) unique, R int: 7943, 3178, 0.038
Criterion for I obs, N(hkl) gt: I obs > 2 σ(I obs), 2979
N(param) refined: 218
Programs: CrysAlisPRO [1], SHELX [2, 3], Mercury [4]
Table 2:

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

Atom x y z U iso*/U eq
O2 0.11051 (12) 0.16554 (10) 0.41846 (9) 0.0256 (2)
O7 −0.05650 (12) −0.00798 (9) 0.74929 (9) 0.0252 (2)
O11 0.62501 (12) 0.08398 (9) 0.02766 (8) 0.0218 (2)
O15 0.37685 (11) 0.49239 (9) 0.62943 (9) 0.0227 (2)
O16 0.15173 (11) 0.51537 (9) 0.77205 (8) 0.0210 (2)
N1 −0.03381 (13) 0.26014 (11) 0.58643 (10) 0.0192 (2)
N3 0.36381 (13) 0.32308 (11) 0.44944 (10) 0.0210 (2)
C2 0.09672 (15) 0.23665 (12) 0.49985 (11) 0.0180 (3)
C3 0.22057 (15) 0.31601 (12) 0.52269 (11) 0.0168 (3)
C4 0.15872 (15) 0.37848 (12) 0.62344 (11) 0.0171 (3)
C5 −0.00996 (15) 0.34710 (12) 0.67152 (11) 0.0182 (3)
H5A 0.000488 0.295627 0.765591 0.022*
H5B −0.108557 0.434339 0.660656 0.022*
C6 −0.18845 (16) 0.21055 (14) 0.58967 (12) 0.0235 (3)
H6A −0.183048 0.162756 0.516621 0.028*
H6B −0.294674 0.292329 0.574819 0.028*
C7 −0.20545 (16) 0.10962 (13) 0.71960 (12) 0.0228 (3)
H7A −0.222266 0.159903 0.791731 0.027*
H7B −0.311069 0.077179 0.714958 0.027*
C8 0.42331 (15) 0.25494 (13) 0.34363 (12) 0.0183 (3)
C9 0.36126 (16) 0.32034 (13) 0.21533 (13) 0.0237 (3)
H9 0.271743 0.407427 0.198590 0.028*
C10 0.42897 (16) 0.25948 (13) 0.11218 (12) 0.0228 (3)
H10 0.385147 0.304037 0.024651 0.027*
C11 0.56138 (15) 0.13291 (12) 0.13611 (11) 0.0175 (3)
C12 0.62112 (15) 0.06565 (12) 0.26465 (12) 0.0176 (3)
H12 0.708970 −0.022341 0.281932 0.021*
C13 0.55152 (15) 0.12793 (12) 0.36767 (11) 0.0175 (3)
H13 0.592751 0.082492 0.455646 0.021*
C14 0.75390 (17) −0.05001 (13) 0.05126 (12) 0.0240 (3)
H14A 0.858124 −0.044962 0.094595 0.029*
H14B 0.787361 −0.076083 −0.033088 0.029*
H14C 0.704607 −0.120876 0.108448 0.029*
C15 0.24119 (15) 0.46570 (12) 0.67301 (11) 0.0178 (3)
C17 0.22268 (18) 0.60931 (14) 0.82359 (12) 0.0246 (3)
H17A 0.228085 0.691792 0.752255 0.029*
H17B 0.343285 0.559982 0.859765 0.029*
C18 0.10359 (18) 0.65577 (14) 0.93055 (13) 0.0257 (3)
H18A 0.100625 0.573518 1.001217 0.031*
H18B −0.015559 0.703724 0.893858 0.031*
H18C 0.147814 0.720445 0.966503 0.031*
H7 −0.058 (3) −0.0669 (17) 0.6883 (15) 0.047 (5)*
H3 0.431 (2) 0.3830 (15) 0.4679 (17) 0.037 (4)*

Source of materials

A mixture of 2,3-dioxopyrrolidine (2.00 g, 9.29 mmol), p-anisidine (1.37 g, 11.15 mmol) and formic acid (0.56 mL, 14.87 mmol) in ethanol was refluxed for 24 h. The solution was concentrated by distillation. The organic mixture was extracted with dichloromethane, washed with water and dried over MgSO4. The solvent was evaporated under reduced pressure and the crude was purified by column chromatography on silica gel (ethyl acetate:petroleum ether, 50:50) to afford 1 as brown solid product (2.34 g, 79%).

Experimental details

The data were indexed and processed using CrysAlisPRO [1]. A multi-scan absorption correction was performed. The structure was solved with SHELXT Version 2018/2 [2] solution program. The model was refined with SHELXL Version 2018/3 [3].

Comment

Pyrrolinones play an important role in organic synthesis and find vast applications in pharmaceutical fields due to their broad range of biological properties such as anti-inflammatory, antifungal, and antibacterial activities [5, 6]. Owing to their notable pharmaceutical effects, they have received tremendous attention over the past few years [7]. Thus, in view of diversifying the structural motifs of these classes of compounds, we decided to prepare the analogue of N-substituted pyrrolinone via amination of 2,3-dioxopyrrolidine with p-anisidine [8]. The starting material, 2,3-dioxopyrrolidine was initially prepared according to the reported procedure [9], [10], [11]. This paper describes the crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate (1).

The crystal structure of 1 is similar to previously reported structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate [12]. All bond angles and lengths are within the normal ranges and comparable to the related structures [12], [13], [14], [15]. The 4-methoxyaniline (N3/C8–C13/O11/C–14) and hydroxyethyl (C6/C7/O7) moieties are observed slightly twisted at N3–C8 and C6–C7 bonds, respectively. The twisted angle of C3–N3–C8–C9 is found to be 87.97° while the twisted angle for N1–C6–C7–O7 is −57.11. The ethyl acetate (O15/O16/C15/C17/C18) and 4-methoxyaniline (N3/C8–C13/O11/C14) moieties are almost perpendicular to each other, subtending a dihedral angle of 86.00°. Meanwhile, the pyrrole ring (N1/C2–C5) forms a dihedral angle of 83.17° with the phenyl ring (C8–C13). In the molecule, an intramolecular N3–H3···O15 hydrogen bond is observed, forming a pseudo six-membered ring, which further stabilizes and lock its atoms in a nearly planar arrangement. A similar feature was observed in the reported structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate [16].

Corresponding author: Mohd Fazli Mohammat, Organic Synthesis Research Laboratory, Institute of Science, Universiti Teknologi MARA, 42300 Bandar Puncak Alam, Selangor, Malaysia, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Forest Research Institute Malaysia (FRIM) and Malaysian Government (MOHE) for the financial support (FRGS/1/2019/STG05/NRE/03/1).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Rigaku Oxford Diffraction. CrysAlisPRO; Rigaku Corp.: Tokyo, Japan, 2021.Search in Google Scholar

2. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M. A short history of Shelx. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar PubMed

4. Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M., Wood, P. A. Mercury 4.0: from visualization to analysis, design and prediction. J. Appl. Crystallogr. 2020, 53, 226–235; https://doi.org/10.1107/s1600576719014092.Search in Google Scholar PubMed PubMed Central

5. Ali, Y., Alam, M. S., Hamid, H., Hussain, A. 2(3H)Pyrrolone – a biologically active scaffold (A review). Orient. J. Chem. 2014, 30, 1–16; https://doi.org/10.13005/ojc/300101.Search in Google Scholar

6. Zali-Boeini, H., Mobin, M., Hajibabaei, K., Ghani, M. Approaches to the construction of substituted 4-amino-1H-pyrrol-2(5 H)-ones. J. Org. Chem. 2012, 77, 5808–5812; https://doi.org/10.1021/jo3004309.Search in Google Scholar PubMed

7. Tan, Q. W., Chovatia, P., Willis, M. C. Copper-catalysed synthesis of alkylidene 2-pyrrolinone derivatives from the combination of α-keto amides and alkynes. Org. Biomol. Chem. 2018, 16, 7797–7800; https://doi.org/10.1039/c8ob02205d.Search in Google Scholar PubMed

8. Bacho, M. Z., Mohammat, M. F., Shaameri, Z., Wibowo, A., Kamarulzaman, F., Hamzah, A. S. A facile synthesis of pyrrolidine-based iminosugars as potential alpha-glucosidase inhibitors. Orient. J. Chem. 2020, 36, 309–319; https://doi.org/10.13005/ojc/360214.Search in Google Scholar

9. Mohammat, M. F., Najim, N., Mansor, N. S., Sarman, S., Shaameri, Z., Zain, M. M., Hamzah, A. S. Synthesis and bioactivity of some 2-oxo-5-aryl-3-hydrazone and 2-oxo-5-aryl-4-hydrazone pyrrolidine derivatives. Arkivoc 2011, ix, 429–438; https://doi.org/10.3998/ark.5550190.0012.932.Search in Google Scholar

10. Abdul Rashid, F. N. A., Mohammat, M. F., Shaameri, Z., Hamzah, A. S. Synthesis of novel 3, 4-fused pyrazolidinone γ-lactam bicyclic moieties from 2,3-dioxo-4-carboxy-5-(substituted) pyrrolidines. Org. Commun. 2019, 12, 121–131; https://doi.org/10.25135/acg.oc.62.19.07.1323.Search in Google Scholar

11. Mohammat, M. F., Shaameri, Z., Hamzah, A. S. Synthesis of 2,3-dioxo-5-(substituted)arylpyrroles and their 2-oxo-5-aryl-3-hydrazone pyrrolidine derivatives. Molecules 2009, 14, 250–256; https://doi.org/10.3390/molecules14010250.Search in Google Scholar PubMed PubMed Central

12. Song, H.-Y., Liu, S., Zhang, B.-N., Zhong, Q.-D., Qi, Y.-J. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 1063–1064; https://doi.org/10.1515/ncrs-2021-0219.Search in Google Scholar

13. Mohammat, M. F., Shaameri, Z., Hamzah, A. S., Fun, H. K., Chantrapromma, S. 4-Hydroxy-5-(4-methoxyphenyl)pyrrolidin-2-one. Acta Crystallogr. 2008, E64, 6979–6981.10.1107/S1600536808003899Search in Google Scholar PubMed PubMed Central

14. Mohammat, M. F., Mansor, N. S., Shaameri, Z., Hamzah, A. S. Diastereoselective reduction of 2,3-dioxo-4-carboxy-5-substituted pyrrolidines using NaBH4/AcOH and heterogenous hydrogenation reactions. J. Kor. Chem. Soc. 2015, 59, 31–35; https://doi.org/10.5012/jkcs.2015.59.1.31.Search in Google Scholar

15. Naganagowda, G., Mahlaka, T. J., Meijboom, R. Crystal structure of methyl-2-methyl-4-(2-oxo-2-phenylethyl)-5-phenyl-1H-pyrrole-3- carboxylate, C21H19NO3. Z. Kristallogr. N. Cryst. Struct. 2017, 232, 63–65; https://doi.org/10.1515/ncrs-2016-0149.Search in Google Scholar

16. Abdul Rashid, F. N. A., Mohammat, M. F., Arshad, S., Shaameri, Z., Hamzah, A. S. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4. Z. Kristallogr. N. Cryst. Struct. 2019, 234, 1137–1139; https://doi.org/10.1515/ncrs-2019-0203.Search in Google Scholar
Received: 2022-10-14
Accepted: 2022-11-25
Published Online: 2022-12-13
Published in Print: 2023-01-27

© 2022 the author(s), published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
https://doi.org/10.1515/ncrs-2022-0497
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
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