Home Physical Sciences Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
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Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P

  • Yifan Liu , Ronghai Cui , Jialing Kang , Xin Jin , Qiang Huang ORCID logo and Jian Zhang EMAIL logo
Published/Copyright: June 3, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 4

Abstract

C21H18BrO3P, monoclinic, P21/c (no. 14), a = 20.2890(9) Å, b = 5.9736(2) Å, c = 16.1577(8) Å, β = 105.371(2)°, V = 1888.24(14) Å3, Z = 4, R gt(F) = 0.1359, wR ref(F 2) = 0.1414, T = 298.00 K.

CCDC no.: 2354776

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: Colorless block
Size: 0.20 × 0.18 × 0.17 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 2.28 mm−1
Diffractometer, scan mode: Bruker Smart-Apex-II, φ and ω
θ max, completeness: 25.0°, >99 %
N(hkl)measured, N(hkl)unique, R int: 25,463, 3310, 0.038
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2799
N(param)refined: 236
Programs: Olex2, 1 , 2 SHELX 3
Table 2:

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

Atom x y z U iso*/U eq
Br1 0.66013 (3) 0.64869 (13) 0.84335 (5) 0.1050 (3)
P1 0.19263 (4) 0.50494 (13) 0.83262 (5) 0.0269 (2)
O1 0.20754 (13) 0.7311 (4) 0.87214 (15) 0.0391 (6)
O2 0.25202 (15) 0.1153 (4) 0.82354 (17) 0.0462 (6)
H2 0.2424 0.0100 0.8507 0.069*
O3 0.39309 (16) 0.1252 (6) 0.9478 (2) 0.0724 (10)
C7 0.18357 (16) 0.5077 (5) 0.7182 (2) 0.0296 (7)
C6 0.11412 (16) 0.3961 (5) 0.84973 (19) 0.0287 (7)
C5 0.07667 (18) 0.5478 (6) 0.8844 (2) 0.0352 (7)
H5 0.0941 0.6903 0.8999 0.042*
C13 0.26336 (17) 0.3087 (5) 0.8756 (2) 0.0322 (7)
H13 0.2658 0.2702 0.9353 0.039*
C1 0.08802 (17) 0.1817 (6) 0.8285 (2) 0.0350 (7)
H1 0.1130 0.0773 0.8067 0.042*
C8 0.1549 (2) 0.3315 (6) 0.6641 (2) 0.0403 (8)
H8 0.1375 0.2079 0.6863 0.048*
C16 0.45737 (18) 0.3828 (6) 0.8899 (2) 0.0384 (8)
C14 0.32857 (17) 0.4248 (6) 0.8696 (2) 0.0373 (8)
H14A 0.3251 0.4563 0.8097 0.045*
H14B 0.3320 0.5671 0.8993 0.045*
C12 0.2089 (2) 0.6902 (6) 0.6836 (2) 0.0404 (8)
H12 0.2281 0.8096 0.7186 0.048*
C10 0.1771 (2) 0.5203 (7) 0.5442 (2) 0.0448 (9)
H10 0.1748 0.5249 0.4860 0.054*
C17 0.45987 (19) 0.5876 (7) 0.8498 (3) 0.0461 (9)
H17 0.4203 0.6731 0.8322 0.055*
C4 0.01363 (19) 0.4884 (7) 0.8962 (2) 0.0441 (9)
H4 −0.0111 0.5911 0.9192 0.053*
C9 0.1520 (2) 0.3387 (7) 0.5777 (2) 0.0470 (9)
H9 0.1329 0.2199 0.5423 0.056*
C2 0.02481 (19) 0.1242 (6) 0.8398 (2) 0.0441 (9)
H2A 0.0072 −0.0181 0.8245 0.053*
C21 0.51713 (19) 0.2585 (7) 0.9160 (3) 0.0483 (9)
H21 0.5165 0.1215 0.9431 0.058*
C15 0.39300 (19) 0.2946 (7) 0.9061 (2) 0.0439 (9)
C3 −0.01232 (18) 0.2771 (7) 0.8737 (3) 0.0473 (9)
H3 −0.0547 0.2373 0.8813 0.057*
C18 0.5196 (2) 0.6661 (7) 0.8357 (3) 0.0524 (10)
H18 0.5207 0.8031 0.8087 0.063*
C11 0.2055 (2) 0.6950 (7) 0.5963 (2) 0.0478 (9)
H11 0.2227 0.8178 0.5734 0.057*
C19 0.57808 (19) 0.5382 (8) 0.8624 (3) 0.0509 (10)
C20 0.5774 (2) 0.3354 (7) 0.9021 (3) 0.0557 (11)
H20 0.6171 0.2507 0.9195 0.067*

1 Source of material

3-(Diphenylphosphoryl)-3-hydroxy-1-phenylpropan-1-one was prepared by the direct difunctionalization of tertiary enaminones with H-phosphine oxide and water. Firstly, the (E)-1-(4-bromophenyl)-3-(dimethylamino)prop-2-en-1-one (compound A) was synthesized through the reaction between 1-(4-bromophenyl)ethan-1-one and N,N–dimethylformamide dimethyl acetal (DMF–DMA) at 363 K for overnight. In this reaction, residual DMF–DMA was removed by reduced pressure distillation, and then the crude product A was purified by flash column chromatography on silicagel (ethyl acetate/petroleum ether = 1:4) to obtain white solid target compound A in 72 % yield. Next, the obtained (E)-1-(4-bromophenyl)-3-(dimethylamino) prop-2-en-1-one (A, 254 mg, 1 mmol) reacted with diphenylphosphine oxide (303 mg, 1.5 mmol) using dried aluminum muriate (266 mg, 2 mmol) in the mixed solvent of tetrahydrofuran (8 ml) and pure water (1 ml) was stirred at 323 K for 3 h. After completion of reaction, the above mixture was filtrated and washed three times by ethyl acetate. The organic liquid was evaporated under vacuum to obtain the residue. The residue was purified by flash column chromatography on silicagel (ethyl acetate/petroleum ether = 1:1) to obtain white solid B as the target compound in 92 % yield. The product B is stable in air.

2 Experimental details

Using Olex2, 1 the structure was solved with the Olex2.solve 2 structure solution program using Charge Flipping and refined with the ShelXL 3 refinement package using CGLS minimization. All hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

Organic phosphorous is attractive because of wide applications in organic and medicinal chemistry. 4 – 6 For example, various α-aminophosphine oxides can be synthesied through the substitution of the OH-group in α-hydroxylphosphorus compounds using amines. 7

In the molecules forming the title crystal structure, the key bond lengths and angles are within normal ranges, and are consistent with those previously reported in similar structures. 8 The C–P bond is confirmed by the distance of P1–C6, P1–C7, P2–C13. Their lengths are 1.808(3) Å°, 1.809(3) Å°, and 1.841(3) Å, respectively. The bond angles for O1–P1–C6, O1–P1–C7, O1–P1–C13 are 110.33(14) Å°, 112.57(14) Å°, and 111.48(15) Å°, which is consistent with O=P–C group. Additionally, the bond angles for C7–P1–C13, C6–P1–C7, C6–P1–C13 at 104.42(15) Å°, 107.73(14) Å°, and 110.10(15) Å° were observed. Meanwhile, the hydroxyl and carbonyl groups are also found by the distance of O2–C13, O3=C15. The bond lengths are 1.412(4) Å° and 1.215(5) Å°.

Corresponding author: Jian Zhang, Department of Pharmacy, West China Hospital, Sichuan University, Chengdu 610041, China, E-mail:

Acknowledgments

This research was supported by National Key Clinical Specialties Construction Program, and the Natural Science Foundation of Guizhou Province (No. QKHJC-ZK[2022]592).

  1. Author contributions: Yifan Liu drafted most parts of the manuscript and conducted the experiments of crystal analysis. Ronghai Cui coordinated the work. Jialing Kang and Jian Zhang co-revised the manuscript. Xin Jin cultured the crystal of compound. Qiang Huang contributed to the analysis of results. All authors agreed to the final version of the manuscript. All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: National Key Clinical Specialties Construction Program, the Natural Science Foundation of Guizhou Province (No. QKHJC-ZK[2022]592).

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

References

1. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

2. Bourhis, L. J.; Dolomanov, O. V.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. The Anatomy of a Comprehensive Constrained, Restrained Refinement Program for the Modern Computing Environment–Olex2 Dissected. Acta Crystallogr. 2015, A71, 59–75; https://doi.org/10.1107/s2053273314022207.Search in Google Scholar

3. Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Yuan, H.; Zhang, Y.; Chen, Z.; Cai, S.; Zhang, Z.; Yang, P.; Peng, S.; Yu, J.; Wang, D.; Zhang, W. Molecular Transformation Pathway and Bioavailability of Organic Phosphorus in Sewage Sludge under Vermicomposting. Sci. Total Environ. 2024, 906, 167796; https://doi.org/10.1016/j.scitotenv.2023.167796.Search in Google Scholar PubMed

5. He, J.; Sun, Z.; Deng, Y.; Liu, Y.; Zheng, P.; Zhang, X.; Cao, S. Air-Induced Hydroxyphosphorylation of α-Trifluoromethyl Styrenes with H-Phosphonates and H-Phosphine Oxides. Eur. J. Org Chem. 2023, 26, e202300719; https://doi.org/10.1002/ejoc.202300719.Search in Google Scholar

6. Zhao, P.; Li, P.; Xiao, J.; Wang, Y.; Hao, X.; Meng, A.; Liu, C. Synthesis and Antitumor Activities of α-Hydroxyamino Phosphine Oxides by Catalyst-Free Hydrophosphinylation of Nitrones. Chem. Commun. 2023, 59, 2614; https://doi.org/10.1039/d2cc06981d.Search in Google Scholar PubMed

7. Troev, K. D. Reactivity of P–H Group of Phosphorus Based Compounds; Troev, K. D., Ed.; Academic Press: Salt Lake City, 2018.10.1016/B978-0-12-813834-2.00002-0Search in Google Scholar

8. Samiee, S.; Kooti, N.; Gable, R. W. Synthesis, Characterization, and Crystal Structure of Mercury(II) Complex Containing New Phosphine Oxide Salt. J. Mol. Struct. 2017, 1129, 319; https://doi.org/10.1016/j.molstruc.2016.09.079.Search in Google Scholar
Received: 2024-04-05
Accepted: 2024-05-12
Published Online: 2024-06-03
Published in Print: 2024-08-27

© 2024 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. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
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  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
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  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
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  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
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  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
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  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 −)
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  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
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https://doi.org/10.1515/ncrs-2024-0159
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]−} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 −)
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
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