Home Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
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Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S

  • Zeng Rong , Hu Ying , Zeng Xiao-Yan , Peng Da-Yong ORCID logo and Zhang Ji ORCID logo EMAIL logo
Published/Copyright: May 31, 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

C12H13NO5S, triclinic, P1̄ (no. 2), a = 9.7095(6) Å, b = 11.9632(6) Å, c = 12.4335(5) Å, α = 86.456(4)°, β = 73.532(4)°, γ = 69.272(5)°, V = 1294.15(12) Å3, Z = 4, Rgt (F) = 0.0445, wRref (F 2) = 0.1113, T = 296(2) K.

CCDC no.: 2351589

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: 0.25 × 0.18 × 0.16 mm
Wavelength:

μ:		 Mo Kα radiation (0.71073 Å)

0.27 mm−1
Diffractometer, scan mode:

θ max, completeness:		 Bruker APEX-II, φ and ω

25.5°, >99 %
N(hkl)measured, N(hkl)unique, R int: 9905, 4814, 0.021
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3836
N(param)refined: 349
Programs: Bruker, 1 SHELX, 2 , 3 Diamond 4
Table 2:

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

Atom x y z U iso*/U eq
C1 0.5513 (3) 0.84105 (19) 0.05240 (19) 0.0407 (5)
C2 0.5974 (3) 0.71499 (18) 0.08980 (18) 0.0364 (5)
C3 0.7533 (3) 0.6501 (2) 0.06579 (19) 0.0422 (6)
H3 0.8237 0.6866 0.0309 0.051*
C4 0.8043 (3) 0.5325 (2) 0.0932 (2) 0.0437 (6)
H4 0.9089 0.4901 0.0795 0.052*
C5 0.6991 (2) 0.47765 (18) 0.14119 (18) 0.0367 (5)
C6 0.5415 (2) 0.54183 (18) 0.16964 (17) 0.0336 (5)
C7 0.4881 (2) 0.66330 (18) 0.14495 (17) 0.0349 (5)
C8 0.3177 (3) 0.7314 (2) 0.1723 (2) 0.0478 (6)
H8A 0.2636 0.6861 0.2216 0.072*
H8B 0.2870 0.7441 0.1043 0.072*
H8C 0.2940 0.8072 0.2085 0.072*
C9 0.4294 (2) 0.48230 (18) 0.22146 (18) 0.0355 (5)
C10 0.3464 (3) 0.4375 (2) 0.1598 (2) 0.0502 (6)
H10A 0.4157 0.3888 0.0934 0.060*
H10B 0.2661 0.5025 0.1388 0.060*
C11 0.2819 (3) 0.3644 (2) 0.2485 (2) 0.0593 (7)
H11A 0.1765 0.3771 0.2514 0.071*
H11B 0.3419 0.2799 0.2336 0.071*
C12 0.7688 (3) 0.3050 (2) 0.3001 (2) 0.0632 (8)
H12A 0.8242 0.3496 0.3193 0.095*
H12B 0.8142 0.2221 0.3144 0.095*
H12C 0.6638 0.3353 0.3448 0.095*
C13 0.7814 (3) 0.0771 (2) 0.56243 (19) 0.0425 (6)
C14 0.6090 (2) 0.13637 (19) 0.59435 (18) 0.0374 (5)
C15 0.5580 (2) 0.2578 (2) 0.57544 (18) 0.0400 (5)
H15 0.6291 0.2954 0.5477 0.048*
C16 0.4038 (2) 0.3235 (2) 0.59708 (19) 0.0407 (5)
H16 0.3711 0.4043 0.5817 0.049*
C17 0.2982 (2) 0.26848 (19) 0.64178 (18) 0.0355 (5)
C18 0.3448 (2) 0.14694 (18) 0.66498 (18) 0.0358 (5)
C19 0.5034 (3) 0.07825 (19) 0.63902 (18) 0.0378 (5)
C20 0.5509 (3) −0.0545 (2) 0.6573 (2) 0.0551 (7)
H20A 0.6225 −0.0975 0.5899 0.083*
H20B 0.4621 −0.0776 0.6762 0.083*
H20C 0.5982 −0.0726 0.7175 0.083*
C21 0.2301 (3) 0.08959 (19) 0.7184 (2) 0.0392 (5)
C22 0.1822 (3) 0.0668 (2) 0.8413 (2) 0.0530 (7)
H22A 0.1503 0.1387 0.8877 0.064*
H22B 0.2632 0.0040 0.8638 0.064*
C23 0.0494 (3) 0.0283 (2) 0.8451 (2) 0.0560 (7)
H23A 0.0553 −0.0430 0.8880 0.067*
H23B −0.0471 0.0912 0.8794 0.067*
C24 0.0396 (3) 0.3258 (2) 0.5607 (2) 0.0518 (6)
H24A −0.0642 0.3774 0.5674 0.078*
H24B 0.0447 0.2441 0.5652 0.078*
H24C 0.1049 0.3364 0.4898 0.078*
N1 0.3961 (2) 0.46637 (18) 0.32590 (16) 0.0483 (5)
N2 0.1658 (2) 0.05364 (18) 0.65959 (18) 0.0516 (5)
O1 0.6469 (2) 0.85588 (15) −0.03931 (16) 0.0687 (6)
H1 0.6181 0.9263 −0.0555 0.103*
O2 0.4384 (2) 0.92137 (15) 0.10294 (16) 0.0709 (6)
O3 0.9341 (2) 0.27951 (15) 0.09338 (17) 0.0736 (7)
O4 0.6787 (2) 0.26533 (14) 0.13316 (16) 0.0615 (5)
O5 0.2900 (2) 0.40554 (18) 0.35174 (16) 0.0647 (5)
O6 0.86247 (18) 0.12963 (15) 0.50452 (15) 0.0522 (5)
O7 0.83477 (19) −0.02818 (16) 0.59976 (16) 0.0599 (5)
H7 0.9282 −0.0556 0.5732 0.090*
O8 0.09568 (18) 0.48260 (14) 0.65806 (16) 0.0574 (5)
O9 0.01618 (18) 0.33036 (15) 0.77451 (14) 0.0541 (5)
O10 0.0618 (2) 0.00419 (17) 0.73001 (17) 0.0653 (5)
S1 0.77667 (7) 0.31963 (5) 0.15816 (5) 0.04698 (19)
S2 0.10023 (6) 0.36139 (5) 0.66954 (5) 0.04096 (17)

1 Source of materials

Compound methyl 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoate and twice the amount of NaOH solid were added to the round-bottom flask under stirring, and the reaction was carried out for 5 h at 50 °C with an appropriate amount of methanol as solvent. The title compound crystals were obtained by slow evaporation of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid at room temperature over a week. After one week, the crystals suitable for X-ray analysis were obtained.

2 Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.90–0.97 Å with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms.

3 Comment

Topramezone is an inhibitor of hydroxyphenylacetonate oxidase, which can inhibit the synthesis of hydroxyphenylacetonate oxidase (4–HPPD) and plastoquinone, and indirectly interfere with the synthesis of carotenoids, disrupting the function of chloroplasts and causing tissue necrosis in plants. 5 , 6 Mainly used for post seedling stem and leaf treatment in corn fields to control annual grasses and broad-leaved weeds, with high safety for corn. In recent years, it has become the preferred choice for controlling corn weeds. 7 , 8 .

In the molecules of the title structure bond lengths and angles are very similar to those given in the literature. 9 , 10 In the title structure, there are two independent molecules (A and B) in each asymmetric unit. The dihydroisoxazole rings are in envelope configuration. The dihydroisoxazole rings are almost perpendicular to the plane of benzene ring, and the dihedral angles between them are 87.3° and 87.7°, respectively. The carboxyl group and benzene ring are not on the same plane, and the dihedral angles between them are 33.2° and 13.6°, respectively. The torsion angles of C6 – C5 – S1 – C12 and C16 – C17 – S2 – C24 are −80.5° and 103.4°, respectively. Intermolecular O – H⋯O hydrogen bonds connect adjacent molecules A and B to form two dimers. In addition, weak intermolecular C – H⋯O hydrogen bonds and C – H⋯N hydrogen bonds contribute to the stability of the crystal structure.

Corresponding author: Zhang Ji, College of Forestry, Jiangxi Agricultural University, East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration, The Institute of Plant Natural Products and Forest Products Chemical Engineering, Nanchang 330045, People’s Republic of China, E-mail:

Acknowledgments

X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, People’s Republic of China.

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

  2. Competing interests: The authors declare no conflicts of interest regarding this article.

  3. Research funding: This work was supported by Jiangxi Province Major science and technology R & D special project (20203ABC28W016), Jiangxi Province Forestry Bureau Camphor Tree Research Special Project (2020CXZX07), College Students’ Innovative Entrepreneurial Training Plan Program (202310410006), the Earmarked Fund for the Youthful Innovation Research Team of Jiangxi Agricultural University-05, the Jiangxi Provincial Forestry Bureau’s Science and Technology Innovation Project Innovation Special Project (2024–3).

References

1. Bruker APEX2, SAINT and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2009.Search in Google Scholar

2. 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

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

5. Peppers, J. M.; Elmore, M. T.; Askew, S. D. Evaluation of Goosegrass Response to Combinations of Topramezone and Chlorothalonil. Weed Technol. 2023, 37, 554–559; https://doi.org/10.1017/wet.2023.67.Search in Google Scholar

6. Ma, Y. L.; Guo, C. L.; Wang, Y. H.; Gao, Y. Y.; Qin, J. L.; Wei, J. L. Herbicidal Activity Evaluation of Topramezone and its Safety to Sugarcane. Sugar Tech. 2023, 25, 698–704; https://doi.org/10.1007/s12355–022–01226-z.10.1007/s12355-022-01226-zSearch in Google Scholar

7. Grossmann, K.; Ehrhardt, T. On the Mechanism of Action and Selectivity of the Corn Herbicide Topramezone: a New Inhibitor of 4-hydroxyphenylpyruvate Dioxygenase. Pest Manag. Sci. 2007, 63, 429–439; https://doi.org/10.1002/ps.1341.Search in Google Scholar PubMed

8. Cutulle, M. A.; Armel, G. R.; Kopsell, D. A.; Wilson, H. P.; Brosnan, J. T.; Vargas, J. J.; Koepke-Hill, R. M. Several Pesticides Influence the Nutritional Content of Sweet Corn. J. Agric. Food Chem. 2018, 66, 3086–3092; https://doi.org/10.1021/acs.jafc.7b05885.Search in Google Scholar PubMed

9. Brunvoll, J.; Colapietro, M.; Domenicano, A.; Marciante, C.; Portalone, G.; Hargittai, I. Molecular Structures of P-Methylsulphonylbenzoic Acid and Methylphenylsulphone: Comparison of X-Ray and Electron Diffraction Results. Z. Naturforsch. B Chem. Sci. 1984, 39 (5), 607–609; https://doi.org/10.1515/znb-1984–0512.10.1515/znb-1984-0512Search in Google Scholar

10. Lian, F. Y.; Yuan, D. Q.; Jiang, F. L.; Hong, M. C. 4, 4′-Sulfonyldibenzoic Acid. Acta Crystallogr. 2007, E63, o2870; https://doi.org/10.1107/S1600536807021216.Search in Google Scholar
Received: 2024-03-17
Accepted: 2024-04-27
Published Online: 2024-05-31
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]
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  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
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  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
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  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
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  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
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  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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  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
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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-2024-0133
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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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