Home The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
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The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3

  • Xianwu Liu ORCID logo , Yifan Li , Changzhou Liao , Yanping Luo ORCID logo and Lanying Wang EMAIL logo
Published/Copyright: November 20, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 1

Abstract

C21H19BrN2O3, orthorhombic, Pna21 (no. 33) a = 25.412(3) Å, b = 21.329(2) Å, c = 7.0020(8) Å, V = 3795.2(7) Å3, Z = 8, R gt (F) = 0.0390, wR ref (F2) = 0.1009, T = 100(2) K.

CCDC no.: 2294922

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 block
Size: 0.12 × 0.12 × 0.10 mm
Wavelength:

μ:		 Ga Kα radiation (1.34138 Å)

2.08 mm−1
Diffractometer, scan mode:

θmax, completeness:		 Bruker Photon III, φ and ω

57.0°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 37012, 7103, 0.051
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 5191
N(param)refined: 517
Programs: Bruker [1], Olex2 [2], SHELX [3]
Table 2:

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

Atom x y z Uiso*/Ueq
Br1A 0.47443 (2) 0.22176 (2) 0.1711 (2) 0.04921 (18)
Br1 0.32938 (2) 0.76592 (2) 0.1710 (3) 0.0575 (2)
C1A 0.37040 (14) 0.27159 (16) 0.177 (2) 0.0334 (10)
C1 0.22730 (13) 0.71064 (15) 0.172 (2) 0.0297 (8)
C2A 0.33434 (13) 0.32056 (17) 0.166 (2) 0.0386 (11)
H2A 0.298013 0.311593 0.149057 0.046*
C2 0.19302 (13) 0.66016 (16) 0.168 (2) 0.0367 (9)
H2 0.156141 0.667467 0.168047 0.044*
C3A 0.35095 (14) 0.38198 (18) 0.178 (2) 0.0388 (11)
C3 0.21162 (14) 0.59952 (17) 0.164 (2) 0.0381 (10)
C4A 0.40373 (15) 0.39636 (19) 0.175 (2) 0.0525 (15)
H4A 0.415075 0.438747 0.169061 0.063*
C4 0.26478 (14) 0.58775 (17) 0.170 (2) 0.0491 (12)
H4 0.277532 0.545905 0.173970 0.059*
C5A 0.43993 (15) 0.3481 (2) 0.183 (2) 0.0519 (17)
H5A 0.476402 0.357305 0.192793 0.062*
C5 0.29937 (15) 0.63774 (18) 0.169 (3) 0.0579 (15)
H5 0.336228 0.630301 0.170228 0.069*
C6A 0.42347 (14) 0.28714 (17) 0.175 (2) 0.0385 (10)
C6 0.28074 (14) 0.69788 (17) 0.165 (2) 0.0371 (10)
C7A 0.35399 (14) 0.20450 (18) 0.164 (2) 0.0425 (11)
H7AA 0.365086 0.186688 0.039330 0.051*
H7AB 0.370486 0.179714 0.266994 0.051*
C7 0.20793 (13) 0.77689 (16) 0.174 (3) 0.0379 (10)
H7A 0.220042 0.798453 0.291550 0.045*
H7B 0.221654 0.799972 0.062200 0.045*
C8A 0.27617 (15) 0.14514 (19) 0.171 (2) 0.0447 (11)
C8 0.12785 (14) 0.83151 (16) 0.1740 (19) 0.0364 (10)
C9A 0.21788 (16) 0.1463 (2) 0.171 (2) 0.0513 (12)
C9 0.06951 (14) 0.82703 (17) 0.175 (2) 0.0387 (10)
C10 0.04430 (16) 0.77310 (18) 0.175 (2) 0.0440 (12)
H10 0.063972 0.735224 0.173244 0.053*
C10A 0.19051 (15) 0.1996 (2) 0.180 (2) 0.0540 (16)
H10Aa 0.208882 0.238325 0.186332 0.065*
H10Bb 0.209493 0.236646 0.209946 0.065*
C11 −0.01476 (15) 0.76990 (19) 0.177 (3) 0.0539 (14)
H11Ec −0.027124 0.760487 0.307767 0.065*
H11Fc −0.026779 0.735752 0.091554 0.065*
H11Gd −0.026469 0.735618 0.262107 0.065*
H11Hd −0.028039 0.761144 0.046584 0.065*
C11Aa 0.1304 (4) 0.1999 (10) 0.179 (6) 0.079 (5)
H11Aa 0.117363 0.231901 0.269494 0.094*
H11Ba 0.117553 0.211143 0.049468 0.094*
C11Bb 0.1318 (6) 0.2065 (19) 0.145 (10) 0.079 (5)
H11Cb 0.113340 0.219953 0.262487 0.094*
H11Db 0.124611 0.237075 0.041899 0.094*
C12Aa 0.1093 (7) 0.1362 (9) 0.234 (3) 0.071 (4)
H12Aa 0.116470 0.128402 0.370962 0.086*
H12Ba 0.070757 0.135163 0.214468 0.086*
C12c −0.0382 (6) 0.8325 (5) 0.110 (3) 0.050 (3)
H12Ec −0.031638 0.838197 −0.028345 0.061*
H12Fc −0.076746 0.832551 0.131154 0.061*
C12′d −0.0367 (8) 0.8328 (8) 0.248 (4) 0.050 (3)
H12Gd −0.075525 0.833576 0.235563 0.061*
H12Hd −0.027510 0.839251 0.384032 0.061*
C12Bb 0.1153 (13) 0.1412 (16) 0.087 (6) 0.071 (4)
H12Cb 0.127180 0.132686 −0.045256 0.086*
H12Db 0.076406 0.137982 0.089729 0.086*
C13A 0.19241 (18) 0.0832 (2) 0.150 (2) 0.0515 (19)
H13Aa 0.205898 0.061927 0.033980 0.062*
H13Ba 0.200474 0.056713 0.261972 0.062*
H13Cb 0.188260 0.072667 0.012824 0.062*
H13Db 0.214307 0.050498 0.210803 0.062*
C13 0.04194 (15) 0.88940 (19) 0.182 (2) 0.0413 (13)
H13Ec 0.057618 0.915224 0.284536 0.050*
H13Fc 0.047452 0.911607 0.059190 0.050*
H13Gd 0.044411 0.906950 0.312322 0.050*
H13Hd 0.059322 0.918990 0.092901 0.050*
C14Aa 0.1093 (4) 0.0304 (4) 0.144 (3) 0.048 (4)
H14Aa 0.117783 0.011950 0.268056 0.072*
H14Ba 0.124507 0.004442 0.041963 0.072*
H14Ca 0.071060 0.032331 0.127955 0.072*
C14 −0.03988 (17) 0.9430 (2) 0.181 (3) 0.0649 (19)
H14Gc −0.021019 0.976177 0.249346 0.097*
H14Hc −0.076351 0.941173 0.226070 0.097*
H14Ic −0.039518 0.952014 0.043649 0.097*
H14Jd −0.021662 0.962384 0.289182 0.097*
H14Kd −0.076531 0.934497 0.215928 0.097*
H14Ld −0.038981 0.971525 0.071213 0.097*
C14Bb 0.1186 (17) 0.0257 (15) 0.227 (10) 0.18 (2)
H14Db 0.080205 0.029793 0.230926 0.266*
H14Eb 0.130326 −0.000127 0.335043 0.266*
H14Fb 0.129149 0.005712 0.107222 0.266*
C15 0.12504 (15) 0.55766 (18) 0.167 (3) 0.0513 (15)
C16 0.0989 (4) 0.5597 (6) 0.3458 (15) 0.046 (3)
H16 0.117738 0.555479 0.462197 0.055*
C17 0.0451 (4) 0.5682 (5) 0.3450 (16) 0.047 (3)
H17 0.026738 0.569558 0.463048 0.056*
C18 0.01841 (16) 0.5744 (2) 0.183 (2) 0.0436 (14)
C19 0.0445 (4) 0.5714 (6) 0.0016 (17) 0.056 (3)
H19 0.025599 0.575272 −0.114909 0.067*
C20 0.0997 (5) 0.5625 (5) 0.0044 (19) 0.063 (4)
H20 0.118539 0.559920 −0.112527 0.076*
C21 −0.03796 (17) 0.5854 (2) 0.171 (2) 0.0528 (13)
C25 0.09983 (16) 0.39487 (18) 0.162 (2) 0.0448 (13)
C27 0.15644 (15) 0.40255 (18) 0.169 (2) 0.0458 (14)
C31 0.26323 (16) 0.41999 (18) 0.176 (2) 0.0488 (15)
C32 0.2381 (4) 0.4159 (6) 0.0042 (18) 0.057 (4)
H32 0.256422 0.419320 −0.113569 0.068*
C35 0.2369 (4) 0.4156 (6) 0.3456 (18) 0.056 (3)
H35 0.256347 0.417953 0.461330 0.067*
C37 0.1828 (4) 0.4078 (7) 0.3545 (16) 0.054 (3)
H37 0.164234 0.406053 0.471991 0.065*
C38 0.1830 (4) 0.4063 (6) 0.0118 (16) 0.054 (3)
H38 0.164528 0.402411 −0.105485 0.065*
N1Aa 0.1312 (5) 0.0935 (5) 0.133 (2) 0.061 (4)
N1c −0.0142 (10) 0.8828 (12) 0.216 (3) 0.056 (4)
N1′d −0.0129 (15) 0.8823 (18) 0.129 (4) 0.056 (4)
N1Bb 0.1422 (11) 0.0867 (12) 0.240 (5) 0.061 (4)
N2A 0.05504 (14) 0.38963 (17) 0.1795 (19) 0.0538 (13)
N2 −0.08232 (15) 0.5944 (2) 0.166 (2) 0.0692 (13)
O1A 0.29718 (9) 0.20253 (12) 0.1807 (14) 0.0405 (9)
O1 0.15120 (9) 0.77502 (11) 0.1689 (15) 0.0389 (7)
O2A 0.30255 (11) 0.09779 (13) 0.1744 (16) 0.0538 (9)
O2 0.15209 (10) 0.88021 (12) 0.1744 (14) 0.0478 (9)
O3A 0.31702 (10) 0.43265 (12) 0.1633 (18) 0.0549 (10)
O3 0.17922 (10) 0.54759 (12) 0.1630 (19) 0.0579 (11)

  1. aOccupancy: 0.639(17), bOccupancy: 0.361(17), cOccupancy: 0.58(2), dOccupancy: 0.42(2).

1 Source of materials

All chemicals were of reagent grade and used without further purification. The synthesis of the title compound was regulated in accord to reference [4] with appropriate modification: arecaine (0.282 g, 2 mmol), 4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile (0.608 g, 2 mmol), and 4–dimethylaminopyridine (0.122 g, 1 mmol) were dissolved in DMF (5 mL) initially, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.575 g, 3 mmol) was added to the mixture. The reaction was then stirred overnight at room temperature, monitored by TLC. After confirmation of the completion, a saturated aqueous NaHCO3 (20 mL) was added, and extracted with ethyl acetate (3 times with 15 mL). The combined organics were washed with water and brine, dried over anhydrous Na2SO4, concentrated in vacuo, and purified through column chromatography to obtain the title compound as white solid. Colourless crystals of the title compound were obtained by slow evaporation (n-hexane/acetone) within one weeks.

2 Experimental details

All hydrogen atoms were placed in the calculated positions and constrained to ride on their parent atoms. Using Olex2 [2], the structure was solved with the XM [3] structure solution program using Dual Space and refined with the XL [3].

3 Comment

Arecoline, an alkaloid that acts on the nervous system [5], is from the areca (betel) nut of the areca palm (Areca catechu) endemic to Southeast Asia, the East African seaboard, and the Western Pacific [6]. In addition to being a naturally occurring psychoactive alkaloid, arecoline also has a variety of physiological activities, such as anti-inflammatory [7], anti-atherosclerotic [8], insecticide and antibacterial activity [9], etc., which have been reviewed [10]. In view of a wide range of physiological activities and important significance in drug development of arecoline, research involving single crystal structures of arecoline derivatives is of great significance to reveal the structure-activity relationship.

The title compound crystallizes in the orthorhombic space group Pna21 with two of the title molecules in the asymmetric unit. They show pseudo-symmetry of a mirror plane as discussed before [11]. Each molecule consists of arecoline (methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate) and diphenyl ethers (4-(4-bromophenoxy)benzonitrile) (see the Figure). A bromine atom and cyano group are connected to the diphenyl ethers with C(6)–Br(1), C(21)–N(2) bonds, respectively. The C(6)–Br(1), C(21)–N(2), C(3)–O(3) and C(15)–O(3) bond lengths were determined as 1.907(4) Å, 1.144(6) Å, 1.380(4) Å and 1.394(5) Å. All bond lengths and angles are in normal ranges [12, 13]. The dihedral angle between the plane through C(1)–C(6) and the plane through C(15)–C(20) is 91.3(4)∘. The centroid distance between the benzene rings is 4.770(4) Å.

Corresponding author: Lanying Wang, School of Tropical Agriculture and Forestry, Hainan University, 570228, Haikou, China, E-mail:

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

  2. Research funding: National Natural Science Foundation of China grant (32260685).

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

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Received: 2023-10-07
Accepted: 2023-11-03
Published Online: 2023-11-20
Published in Print: 2024-02-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

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  35. (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
  36. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
  37. Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
  38. Crystal structure of catena-poly[triaqua-(μ2-1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-O,O′:O″)cobalt(II)], C12H12N2O8Co
  39. Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
  40. Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6
  41. Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
  42. The crystal structure of triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ3N,O,O)nickel(II) monohydrate, C12H15NO9Ni
  43. Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
  44. The crystal structure of 1-(carboxymethyl)-1H-imidazole 3-oxide
  45. The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
  46. Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
  47. Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S
https://doi.org/10.1515/ncrs-2023-0438
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
  8. Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
  9. The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
  10. Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
  11. Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
  12. Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
  15. Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
  16. The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
  17. Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
  19. The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
  20. Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  21. The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
  22. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
  23. The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
  24. Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
  25. The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
  26. Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
  27. Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
  28. Crystal structure of langite from Mine du Pradet (France)
  29. The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
  30. Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
  31. The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
  32. The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
  33. Synthesis and crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino) ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C40H46CoN4O4
  34. Crystal structure of tetraaqua-[(1-(carboxymethyl)-1H-pyrazole-3-carboxylato-κ2N,O)cobalt(II)], C6H12CoN2O8
  35. (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
  36. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
  37. Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
  38. Crystal structure of catena-poly[triaqua-(μ2-1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-O,O′:O″)cobalt(II)], C12H12N2O8Co
  39. Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
  40. Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6
  41. Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
  42. The crystal structure of triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ3N,O,O)nickel(II) monohydrate, C12H15NO9Ni
  43. Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
  44. The crystal structure of 1-(carboxymethyl)-1H-imidazole 3-oxide
  45. The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
  46. Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
  47. Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S
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