Home The crystal structure of 1,8-bis(4-methoxybenzoyl)naphthalene-2,7-diyl dibenzoate, C40H28O8
Article Open Access

The crystal structure of 1,8-bis(4-methoxybenzoyl)naphthalene-2,7-diyl dibenzoate, C40H28O8

  • Miyuki Kobayashi , Kikuko Iida , Hiroaki Iitsuka , Kun Li , Noriyuki Yonezawa and Akiko Okamoto ORCID logo EMAIL logo
Published/Copyright: June 23, 2021
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 5

Abstract

C40H28O8, orthorhombic, Pna21 (no. 33), a = 27.0291(4) Å, b = 14.5593(2) Å, c = 7.95172(10) Å, V = 3129.20(7) Å3, Z = 4, R gt (F) = 0.0276, wR ref (F 2) = 0.0690, T = 193 K.

CCDC no.: 2084108

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: 0.40 × 0.30 × 0.10 mm
Wavelength: Cu Kα radiation (1.54187 Å)
μ: 0.78 mm−1
Diffractometer, scan mode: Rigaku R-AXIS RAPID, ω
θ max, completeness: 68.2°, >99%
N(hkl)measured, N(hkl)unique, R int: 44,449, 5717, 0.032
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 5474
N(param)refined: 436
Programs: Rigaku [1], [2], SIR2004 [3], SHELX [4], ORTEP-III [5], PLATON [6]
Table 2:

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

Atom x y z U iso*/U eq
O1 0.29041 (5) 0.41345 (10) 0.86408 (19) 0.0422 (3)
O2 0.13130 (6) 0.13796 (11) 1.1669 (2) 0.0505 (4)
O3 0.26450 (5) 0.28654 (9) 0.5490 (2) 0.0403 (3)
O4 0.49626 (6) 0.24230 (11) 0.6109 (3) 0.0622 (5)
O5 0.16377 (5) 0.50203 (10) 0.92579 (17) 0.0367 (3)
O6 0.09082 (6) 0.46659 (13) 0.8054 (2) 0.0544 (4)
O7 0.33903 (5) 0.41496 (9) 0.24556 (18) 0.0368 (3)
O8 0.39186 (6) 0.53448 (11) 0.2487 (3) 0.0653 (5)
C1 0.22243 (7) 0.46811 (13) 0.7096 (2) 0.0323 (4)
C2 0.18339 (7) 0.52016 (14) 0.7655 (3) 0.0363 (4)
C3 0.16461 (8) 0.59593 (15) 0.6767 (3) 0.0420 (5)
H3 0.137524 0.630192 0.719852 0.050*
C4 0.18584 (8) 0.61926 (14) 0.5282 (3) 0.0407 (5)
H4 0.173861 0.671224 0.468495 0.049*
C5 0.24628 (7) 0.59382 (14) 0.3044 (3) 0.0384 (5)
H5 0.233473 0.645536 0.245988 0.046*
C6 0.28432 (7) 0.54571 (14) 0.2374 (3) 0.0389 (5)
H6 0.298509 0.563885 0.133266 0.047*
C7 0.30253 (7) 0.46888 (13) 0.3232 (3) 0.0344 (4)
C8 0.28322 (7) 0.43827 (13) 0.4732 (3) 0.0319 (4)
C9 0.24404 (7) 0.49011 (12) 0.5495 (2) 0.0314 (4)
C10 0.22535 (7) 0.56790 (14) 0.4607 (3) 0.0350 (4)
C11 0.24682 (7) 0.40204 (13) 0.8329 (3) 0.0331 (4)
C12 0.21717 (7) 0.33013 (13) 0.9162 (2) 0.0332 (4)
C13 0.23196 (7) 0.29951 (13) 1.0742 (3) 0.0372 (4)
H13 0.261607 0.322872 1.122056 0.045*
C14 0.20447 (7) 0.23586 (15) 1.1630 (3) 0.0401 (5)
H14 0.214743 0.216418 1.271590 0.048*
C15 0.16175 (7) 0.20081 (13) 1.0915 (3) 0.0383 (5)
C16 0.14703 (8) 0.22875 (14) 0.9315 (3) 0.0392 (5)
H16 0.118268 0.203033 0.881516 0.047*
C17 0.17416 (7) 0.29355 (14) 0.8461 (3) 0.0360 (4)
H17 0.163532 0.313603 0.738288 0.043*
C18 0.14346 (10) 0.10974 (18) 1.3333 (3) 0.0570 (6)
H18A 0.145922 0.163815 1.406193 0.068*
H18B 0.175225 0.077275 1.332191 0.068*
H18C 0.117622 0.068685 1.375994 0.068*
C19 0.29736 (7) 0.34343 (13) 0.5353 (2) 0.0337 (4)
C20 0.34972 (7) 0.32091 (13) 0.5668 (3) 0.0356 (4)
C21 0.36423 (8) 0.22857 (14) 0.5707 (3) 0.0422 (5)
H21 0.339964 0.181619 0.561617 0.051*
C22 0.41302 (8) 0.20543 (15) 0.5874 (4) 0.0496 (6)
H22 0.422356 0.142538 0.589969 0.060*
C23 0.44902 (8) 0.27307 (16) 0.6007 (3) 0.0470 (5)
C24 0.43507 (8) 0.36500 (15) 0.6039 (3) 0.0462 (5)
H24 0.459316 0.411667 0.617341 0.055*
C25 0.38586 (7) 0.38792 (14) 0.5873 (3) 0.0399 (5)
H25 0.376431 0.450767 0.589881 0.048*
C26 0.53508 (9) 0.3078 (2) 0.6011 (5) 0.0716 (8)
H26A 0.533231 0.349302 0.697866 0.086*
H26B 0.531783 0.343284 0.496972 0.086*
H26C 0.567026 0.275940 0.601610 0.086*
C27 0.11558 (8) 0.47378 (14) 0.9297 (3) 0.0387 (5)
C28 0.09848 (8) 0.45404 (13) 1.1030 (3) 0.0362 (4)
C29 0.13081 (8) 0.44668 (16) 1.2368 (3) 0.0442 (5)
H29 0.165393 0.453749 1.219787 0.053*
C30 0.11237 (10) 0.42890 (18) 1.3959 (3) 0.0527 (6)
H30 0.134439 0.423525 1.488397 0.063*
C31 0.06230 (10) 0.41897 (18) 1.4210 (3) 0.0564 (6)
H31 0.049884 0.407391 1.530749 0.068*
C32 0.03018 (9) 0.4258 (2) 1.2874 (3) 0.0565 (6)
H32 −0.004362 0.418441 1.304900 0.068*
C33 0.04805 (8) 0.44328 (16) 1.1281 (3) 0.0455 (5)
H33 0.025869 0.447931 1.035841 0.055*
C34 0.38375 (8) 0.45543 (15) 0.2158 (3) 0.0423 (5)
C35 0.42021 (8) 0.39016 (15) 0.1459 (3) 0.0431 (5)
C36 0.40780 (9) 0.30444 (16) 0.0899 (4) 0.0560 (6)
H36 0.374231 0.285137 0.091985 0.067*
C37 0.44404 (11) 0.24566 (19) 0.0301 (4) 0.0706 (8)
H37 0.435204 0.186238 −0.009013 0.085*
C38 0.49228 (11) 0.2726 (2) 0.0272 (4) 0.0666 (8)
H38 0.516992 0.231959 −0.013693 0.080*
C39 0.50526 (10) 0.3585 (2) 0.0833 (5) 0.0781 (9)
H39 0.538913 0.377240 0.081522 0.094*
C40 0.46926 (9) 0.4174 (2) 0.1423 (5) 0.0709 (9)
H40 0.478170 0.476900 0.180721 0.085*

Source of material

The title compound was prepared by reaction of 1,8-bis(4-methoxybenzoyl)-2,7-dihydroxynaphthalene (0.2 mmol, 85.7 mg), which was obtained via P2O5–MsOH [7] -mediated diaroylation of 2,7-dihydroxynaphthalene and 4-methoxybenzoic acid, benzoyl chloride (0.44 mmol, 61.9 mg), and triethylamine (0.22 mmol, 0.03 ml) in dichloromethane (0.5 ml). After the reaction mixture was stirred at room temperature for 3 h, it was poured into water (30 ml) and the mixture was extracted with CHCl3 (10 ml × 3). The combined extracts were washed with sat. NaHCO3 aq. and brine. The organic layers thus obtained were dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give the crude product (94%). 1H NMR δ (400 MHz, CDCl3): 3.73 (6H, s), 6.72 (4H, broad), 7.25 (4H, t, J = 6.4 Hz), 7.46 (2H, t, J = 6.0 Hz), 7.56 (2H, d, J = 7.6 Hz), 7.63 (4H, d, J = 6.0 Hz), 7.69 (4H, broad), 8.10 (2H, d, J = 7.6 Hz) ppm 13C NMR δ (75 MHz, CDCl3): 55.45, 113.52 (overlap), 122.11, 128.31, 128.48, 129.68, 129.99, 130.82, 131.38, 131.54, 133.61, 147.54, 163.64, 164.18, 193.36 ppm. IR (KBr): 3450 (C–H), 2838 (O–CH3), 1735 (OC=O), 1653 (C=O), 1599 (Ar), 1507 (Ar) cm−1. HRMS (m/z): [M+H]+ calcd. for C40H29O8, 637.1863, found, 637.1910. m.p. = 184.6–185.0 °C.

Experimental details

All H atoms were found in a difference map and were subsequently refined as riding atoms, with C―H = 0.95 (aromatic) and 0.98 (methyl) Å, and with U iso(H) = 1.2U eq(C).

Comment

Weak interactions in solid organic molecular substances have acquired growing interests and the consequent revaluation over the last two decades [8], [9], [10]. Since the degree of freedom in arranging aromatic rings is small, crystals of compounds of non-coplanarly accumulated aromatic rings can be expected to distinguish contributions of rather weak non-covalent bonding interactions other than π⃛π stacking interactions or classical hydrogen bonds as structure determining factors [11], [12], [13].

In the molecular structure of the title compound, the benzene rings of 1,8-(4-methoxybenzoyl) groups and those of 2,7-benzoyloxy groups are twisted away from the naphthalene ring (Figure). Two 1,8-(4-methoxybenzoyl) groups are situated in anti-orientation. The dihedral angles between the benzene rings of 4-methoxybenzoyl groups and the naphthalene ring system are 67.41(7)° [C20–C25 ring, C7–C8–C19–O3 torsion angle = –116.81(15)°] and 73.77 (6)° [C12–C17 ring C2–C1–C11–O1 torsion angle = –119.46(15)°], respectively. The dihedral angle between the best planes of the two phenyl rings is 63.18(8)°. The two benzoyloxy groups at 2,7-positions of the naphthalene moiety are also situated in opposite directions. The dihedral angles between their benzene rings [C35–C40 ring and C28–C33 ring] and the naphthalene ring system are 72.13(9)° and 53.08(7)°, respectively. The two benzene rings make a dihedral angle of 77.55(10)°. The phenyl rings and carbonyloxy moieties are almost coplanar [O8–C34–C35–C36 torsion angle = −171.15(19)° and O6–C27–C28–C29 torsion angle = 167.41(16)°]. Several non-classical hydrogen bonds exhibiting almost similar interatomic distances are also confirmed: C–H(methoxy)⃛O=C(benzoyl) (2.57 Å, H18B⃛O1; 1/2−x, −1/2+y, 1/2+z), C–H(naphthalene)⃛O=C(benzoyl) (2.58 Å, H5⃛O3; 1/2−x, −1/2+y, 1/2+z), C–H(benzoyloxy)⃛OMe (2.60 Å, H39⃛O2; 1/2+x, 1/2−y, −1+z), and and C–H(benzoyloxy)⋯O(benzoyloxy) (2.60 Å, H31⃛O6; x, y, 1+z). The first three non-classical hydrogen bonds are parallel to the glide planes, and the last one is oriented along the c axis. The authors reported the crystal structure of the homologous compounds [2,7-dimethoxy-8-(4-methoxybenzoyl)-naphthalen-1-yl](4-methoxyphenyl)methanone chloroform monosolvate (I) [14] and 1,8-dibenzoylnaphthalene-2,7-diyl dibenzoate (II) [15]. The title compound and the homologue II shows unsymmetric spatial situation of 1,8-diaroyl groups on naphthalene ring [dihedral angles between phenyl rings and naphthalene: 67.41(7)° and 73.77(6)° for the title compound, 67.12(5)° and 85.15(5)° for homologue II, and 72.51(7)° and 73.33(7)° for homologue I]. Two benzoyloxy groups in homologue II are twisted to the naphthalene ring with almost same dihedral angles [71.47(5)° and 76.41(5)° vs. 72.13(9)° and 53.08(7)° for the title compound]. In these compounds, fewer non-classical hydrogen bonds than in the packing of the title compound are observed, e.g. C–H(naphthalene)⃛OMe for homologue I, C–H(benzoyl)⃛O=C(benzoyl) and C–H(benzoyloxy)⃛π(naphthalene) for homologue II. More effective factors stabilize their crystals such as co-crystallization with solvent molecules or π⃛π stacking interactions. In other words, continuous neighbouring substitution of 4-methoxybenzoyl groups and benzoyloxy group disturb the effective interactions other than non-classical hydrogen bonds in title compound. Concludingly, neighbourly aligned four benzene rings on naphthalene ring afford enough stabilization with the aid of maximum number of non-classical hydrogen bonds in the absence of π⃛π stacking. The magnitude of the stabilization satisfactorily compensates those expected by intermolecular interaction of crystal solvent.

Corresponding author: Akiko Okamoto, Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo, Japan, E-mail:

Funding source: JSPS KAKENHI

Award Identifier / Grant number: JP20K05473

Acknowledgement

The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for technical advice.

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

  2. Research funding: JSPS KAKENHI Grant Number JP20K05473. Tokyo Ohka Foundation for The Promotion of Science and Technology Grant Number 216065.

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

References

1. Rigaku. PROCESS-AUTO; Rigaku Corporation: Tokyo, Japan, 1998.Search in Google Scholar

2. Rigaku. CRYSTALSTRUCTURE; Rigaku Corporation: Tokyo, Japan, 2010.Search in Google Scholar

3. Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Spagna, R. SIR2004: an improved tool for crystal structure determination and refinement. J. Appl. Crystallogr. 2005, 38, 381–388; https://doi.org/10.1107/s002188980403225x.Search in Google Scholar

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

5. Burnett, M. N., Johnson, C. K. ORTEPIII. Report ORNL-6895; Oak Ridgeational Laboratory: Tennessee, USA, 1996.Search in Google Scholar

6. Spek, A. L. Structure validation in chemical crystallography. Acta Crystallogr. 2009, D65, 148–155; https://doi.org/10.1107/s090744490804362x.Search in Google Scholar PubMed PubMed Central

7. Eaton, P., Carlson, G. R., Lee, J. T. Phosphorus pentoxide-methane sulfonic acid. convenient alternative to polyphosphoric acid. J. Org. Chem. 1973, 38, 4071–4073; https://doi.org/10.1021/jo00987a028.Search in Google Scholar

8. Desiraju, G. R., Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.Search in Google Scholar

9. Desiraju, G. R. C–H⃛O and other weak hydrogen bonds. from crystal engineering to virtual screening. Chem. Commun. 2005, 24, 2995–3001; https://doi.org/10.1039/b504372g.Search in Google Scholar PubMed

10. Taylor, R., Kennard, O. Crystallographic evidence for the existence of C–H⃛O, C–H⃛N, and C–H⃛Cl hydrogen bonds. J. Am. Chem. Soc. 1982, 104, 5063–5070; https://doi.org/10.1021/ja00383a012.Search in Google Scholar

11. Okamoto, A., Yonezawa, N. Unique and specific reaction behavior and characteristic spatial organization of non-coplanarly aromatic-ring-accumulated molecular compounds. J. Synth. Org. Chem. 2015, 73, 339–360; https://doi.org/10.5059/yukigoseikyokaishi.73.339.Search in Google Scholar

12. Muto, T., Iida, K., Noguchi, K., Yonezawa, N., Okamoto, A. Crystal structure and Hirshfeld surface analysis of 2-hydroxy-7-methoxy-1,8-bis(2,4,6-trichlorobenzoyl)naphthalene. Acta Crystallogr. 2019, E75, 1418–1422; https://doi.org/10.1107/s2056989019012118.Search in Google Scholar PubMed PubMed Central

13. Iitsuka, H., Li, K., Kobayashi, M., Iida, K., Yonezawa, N., Okamoto, A. Crystal structure of 1,2-bis(4-fluorophenyl)-1-hydroxy- 2,3,8-trimethoxyacenaphthene: formation of a five-membered intramolecular O–H⃛O hydrogen-bonded ring. Acta Crystallogr. 2021, E77, 175–179; https://doi.org/10.1107/s2056989021000669.Search in Google Scholar

14. Sasagawa, K., Sakamoto, R., Kusakabe, T., Okamoto, A., Yonezawa, N. [2,7–Dimethoxy-8-(4-methoxybenzoyl)nephthalen-1-yl](4-methoxyphenyl)methanone chloroform monosolvate. Acta Crystallogr. 2013, E69, o146; https://doi.org/10.1107/s1600536812050799.Search in Google Scholar PubMed PubMed Central

15. Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A., Yonezawa, N. 1,8–Dibenzoylnaphthalene-2,7-diyl dibenzoate. Acta Crystallogr. 2012, E68, o2454; https://doi.org/10.1107/S1600536812030991.Search in Google Scholar PubMed PubMed Central

Received: 2021-04-27
Accepted: 2021-05-17
Published Online: 2021-06-23
Published in Print: 2021-09-27

© 2021 Miyuki Kobayashi et al., 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 [aqua-(4-iodopyridine-2,6-dicarboxylato-κ3 O,N,O′)-(1,10-phenanothroline-κ2 N,N′)copper(II)] dihydrate, C19H16O7N3CuI
  4. The crystal structure of tetrakis(1-isopropyl-1H-imidazolium) octamolybdate, C24H44Mo8N8O26
  5. Crystal structure of catena-poly[bis(µ2-3,5-bis(1-imidazolyl)pyridine-κ2 N:N′)-(µ2-3-nitrophthalato-k3 O,O′:O″)cadmium(II)] dihydrate, C30H25N11O8Cd
  6. The crystal structure of diaqua-bis(2-(3-(1H-pyrazol-4-yl)-1H-1,2,4-triazol-5-yl)pyridine-κ2 N:N′)-bis(3,5-dicarboxybenzoato-κ1 O)cobalt(II), C38H30CoN12O14
  7. Crystal structure of the nickel(II) complex aqua-(2,6-di(pyrazin-2-yl)-4,4′-bipyridine-κ3 N,N′,N′′)-(phthalato-κ2 O,O′)nickel(II) tetrahydrate, C26H26N6O9Ni
  8. The crystal structure of 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-methylmethanaminium 3-carboxyprop-2-enoate, C21H20FN3O6S
  9. The crystal structure of 1,2-bis(4-pyridyl)ethane - 4,4-dihydroxydiphenylmethane (1/1), C25H21N2O2
  10. Crystal structure of bis(2-((E)-5-chloro-2-hydroxybenzylidene)hydrazineyl)methaniminium trifluoroacetate dihydrate, C34H36Cl4N10O12
  11. Crystal structure of 1-cyclopropyl-7-ethoxy-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C15H13F2NO4
  12. Crystal structure of methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)benzoate, C18H15BN2O2
  13. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-2-hydroxybenzohydrazide, C14H11ClN2O3
  14. Crystal structure of Al-rich fluorophlogopite, K1.0(Mg2.8Al0.2)(Si2.8Al1.2)O10F2
  15. The crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium hexafluoridoantimonate(V), C20H22F6I2N3Sb
  16. Crystal structure of tris(3-iodopyridin-1-ium) catena-poly[(hexachlorido-κ1 Cl)-(μ2-trichlorido-κ2 Cl:Cl)diantimony(III)], C15H15Cl9I3N3Sb2
  17. Crystal structure of methyl 2-(1H-naphtho[1,8-de][1.3.2]diazaborinin-2(3H-yl)benzoate C18H15BN2O2
  18. The crystal structure of 1,8-bis(4-methoxybenzoyl)naphthalene-2,7-diyl dibenzoate, C40H28O8
  19. Crystal structure of 2-bromo-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4
  20. The crystal structure of (E)-3-chloro-2-(2-(2-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  21. Crystal structure of bis(µ2- 4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(µ2-1-(4-pyridyl)piperazine-κ2N:N′)-hexa-aqua-tetra-copper(II), C46H46Cu4I4N10O22
  22. Crystal structure of poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ2O:O′)(μ2-bis(4-pyridylformyl)piperazine-κ2N:N′)cadmium(II)] dihydrate, C24H28CdN4O12
  23. Crystal structure of poly[aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(μ3-2,3,5,6-tetrafluoroterephthalato-κ3O:O′:O′′)cadmium(II)], C17H14N4O5F4Cd
  24. Crystal structure of 6-(quinolin-8-yl)benzo[a]phenanthridin-5(6H)-one, C26H16N2O
  25. The crystal structure of aqua-bis(6-chloropicolinato-κ2N,O)copper(II), C12H8Cl2N2O5Cu
  26. Crystal structure of catena-poly[diaqua-bis(μ2-4,4′-bipyridyl-κ2N:N′) disilver(I)] 4-oxidopyridine-3-sulfonate trihydrate, C25H29Ag2N5O9S
  27. The crystal structure of 4-(3-bromophenyl)pyrimidin-2-amine, C10H8BrN3
  28. Crystal structure of 6-oxo-4-phenyl-1-propyl-1,6-dihydropyridine-3-carbonitrile, C15H14N2O
  29. Crystal structure of 4-(2,2-difluoroethyl)-2,4-dimethyl-6-(trifluoromethyl)isoquinoline-1,3(2H,4H)-dione, C14H12F5NO2
  30. Crystal structure of dibromido-(1-methyl-1H-imidazole-κ1N)-(3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoato-κ1O)zinc(II), C11H16Br2N4O2Zn
  31. The crystal structure of 1,1′-(((2 (dimethylamino)ethyl)azanediyl)bis(methylene)) bis(naphthalen-2-olato-κ4 N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)- titanium(IV) ─ dichloromethane (2/1), C33H29N3O6Ti
  32. The layered crystal structure of bis(theophyllinium) hexachloridostannate (IV), C14H18N8O8SnCl6
  33. The crystal structre of 3-(1-ethenyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate, C8H12N2O3S
  34. Synthesis and crystal structure of di-tert-butyl 1″-acetyl-2,2″,9′-trioxo-4a′,9a′-dihydro-1′H,3′H,9′H-dispiro[indoline-3,2′-xanthene-4′,3″-indoline]-1,3′-dicarboxylate, C39H38N2O9
  35. The crystal structure of 4-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  36. The crystal structure of 1-fluoro-4-(p-tolylethynyl)benzene, C15H11F
  37. The crystal structure of bis[4-bromo-2-(1H-pyrazol-3-yl) phenolato-κ2N,O] copper(II), C18H12Br2CuN4O2
  38. The crystal structure of poly[(μ 3-imidazolato-κ 3 N:N:N′)(tetrahydrofuran- κ 1 O)lithium(I)], C7H11LiN2O
  39. Crystal structure of N′,N′′′-((1E,1′E)-(propane-2,2-diylbis(1H-pyrrole-5,2diyl))bis(methaneylylidene))di(nicotinohydrazide) pentahydrate, C25H24N8O2·5H2O
  40. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-ethyl-1H-imidazol-3-ium hexafluoridophos-phate(V), C9H15F6N2O2P
  41. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(3-thiophenecarboxylato-κ2O,O′)copper(II), C22H14N2O4S2Cu
  42. The crystal structure of 2-amino-3-carboxypyridin-1-ium iodide hemihydrate, C6H8IN2O2.5
  43. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-2-yl)methylene)-tetralone, C18H17NO3
  44. The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br
  45. The crystal structure of 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
  46. The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2
  47. Crystal structure of monocarbonyl(N-nitroso-N-oxido-phenylamine-κ 2 O,O′)(tricyclohexylphosphine-κP)rhodium(I), C25H39N2O3PRh
  48. Crystal structure of poly[bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N:N′:N″]nickel(II)] hexafluorosilicate, C36H36N12NiSiF6
  49. The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
  50. Crystal structure of 3,5-bis((E)-4-methoxy-2-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  51. The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
  52. Crystal structure of (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  53. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
  54. The crystal structure of cis-diaqua-bis (N-butyl-N-(pyridin-2-yl)pyridin-2-amine-κ2N,N′)cobalt(II)] dichloride trihydrate, C28H44Cl2N6O5Co
  55. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3
  56. Crystal structure of (E)-2-((3-fluoropyridin-4-yl)methylene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  57. The crystal structure of 6-bromohexanoic acid, C6H11BrO2
  58. The crystal structure of 4-chloro-thiophenol, C6H5ClS
  59. The crystal structure of 4-bromobenzyl chloride, C7H6BrCl
  60. The crystal structure of di-tert-butyl dicarbonate, C10H18O5
  61. The crystal structure of (2-(4-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  62. The crystal structure of the co-crystal: 2-hydroxybenzoic acid – N′-(butan-2-ylidene)pyridine-4-carbohydrazide, C10H13N3O·C7H6O3
  63. Crystal structure and anti-inflammatory activity of (E)-7-fluoro-2-((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  64. Crystal structure of (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  65. Crystal structure of 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C32H56F24N8P4
  66. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2)-cadmium(II), C14H20CdCl2N4O4
  67. Crystal structure of 1-(2-cyanobenzyl)-3-cyano-4-phenyl-4-(2-cyanobenzyl)-1,4-dihydropyridine monohydrate, C56H42N8O
  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
https://doi.org/10.1515/ncrs-2021-0160
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of [aqua-(4-iodopyridine-2,6-dicarboxylato-κ3 O,N,O′)-(1,10-phenanothroline-κ2 N,N′)copper(II)] dihydrate, C19H16O7N3CuI
  4. The crystal structure of tetrakis(1-isopropyl-1H-imidazolium) octamolybdate, C24H44Mo8N8O26
  5. Crystal structure of catena-poly[bis(µ2-3,5-bis(1-imidazolyl)pyridine-κ2 N:N′)-(µ2-3-nitrophthalato-k3 O,O′:O″)cadmium(II)] dihydrate, C30H25N11O8Cd
  6. The crystal structure of diaqua-bis(2-(3-(1H-pyrazol-4-yl)-1H-1,2,4-triazol-5-yl)pyridine-κ2 N:N′)-bis(3,5-dicarboxybenzoato-κ1 O)cobalt(II), C38H30CoN12O14
  7. Crystal structure of the nickel(II) complex aqua-(2,6-di(pyrazin-2-yl)-4,4′-bipyridine-κ3 N,N′,N′′)-(phthalato-κ2 O,O′)nickel(II) tetrahydrate, C26H26N6O9Ni
  8. The crystal structure of 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-methylmethanaminium 3-carboxyprop-2-enoate, C21H20FN3O6S
  9. The crystal structure of 1,2-bis(4-pyridyl)ethane - 4,4-dihydroxydiphenylmethane (1/1), C25H21N2O2
  10. Crystal structure of bis(2-((E)-5-chloro-2-hydroxybenzylidene)hydrazineyl)methaniminium trifluoroacetate dihydrate, C34H36Cl4N10O12
  11. Crystal structure of 1-cyclopropyl-7-ethoxy-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C15H13F2NO4
  12. Crystal structure of methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)benzoate, C18H15BN2O2
  13. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-2-hydroxybenzohydrazide, C14H11ClN2O3
  14. Crystal structure of Al-rich fluorophlogopite, K1.0(Mg2.8Al0.2)(Si2.8Al1.2)O10F2
  15. The crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium hexafluoridoantimonate(V), C20H22F6I2N3Sb
  16. Crystal structure of tris(3-iodopyridin-1-ium) catena-poly[(hexachlorido-κ1 Cl)-(μ2-trichlorido-κ2 Cl:Cl)diantimony(III)], C15H15Cl9I3N3Sb2
  17. Crystal structure of methyl 2-(1H-naphtho[1,8-de][1.3.2]diazaborinin-2(3H-yl)benzoate C18H15BN2O2
  18. The crystal structure of 1,8-bis(4-methoxybenzoyl)naphthalene-2,7-diyl dibenzoate, C40H28O8
  19. Crystal structure of 2-bromo-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4
  20. The crystal structure of (E)-3-chloro-2-(2-(2-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  21. Crystal structure of bis(µ2- 4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(µ2-1-(4-pyridyl)piperazine-κ2N:N′)-hexa-aqua-tetra-copper(II), C46H46Cu4I4N10O22
  22. Crystal structure of poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ2O:O′)(μ2-bis(4-pyridylformyl)piperazine-κ2N:N′)cadmium(II)] dihydrate, C24H28CdN4O12
  23. Crystal structure of poly[aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(μ3-2,3,5,6-tetrafluoroterephthalato-κ3O:O′:O′′)cadmium(II)], C17H14N4O5F4Cd
  24. Crystal structure of 6-(quinolin-8-yl)benzo[a]phenanthridin-5(6H)-one, C26H16N2O
  25. The crystal structure of aqua-bis(6-chloropicolinato-κ2N,O)copper(II), C12H8Cl2N2O5Cu
  26. Crystal structure of catena-poly[diaqua-bis(μ2-4,4′-bipyridyl-κ2N:N′) disilver(I)] 4-oxidopyridine-3-sulfonate trihydrate, C25H29Ag2N5O9S
  27. The crystal structure of 4-(3-bromophenyl)pyrimidin-2-amine, C10H8BrN3
  28. Crystal structure of 6-oxo-4-phenyl-1-propyl-1,6-dihydropyridine-3-carbonitrile, C15H14N2O
  29. Crystal structure of 4-(2,2-difluoroethyl)-2,4-dimethyl-6-(trifluoromethyl)isoquinoline-1,3(2H,4H)-dione, C14H12F5NO2
  30. Crystal structure of dibromido-(1-methyl-1H-imidazole-κ1N)-(3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoato-κ1O)zinc(II), C11H16Br2N4O2Zn
  31. The crystal structure of 1,1′-(((2 (dimethylamino)ethyl)azanediyl)bis(methylene)) bis(naphthalen-2-olato-κ4 N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)- titanium(IV) ─ dichloromethane (2/1), C33H29N3O6Ti
  32. The layered crystal structure of bis(theophyllinium) hexachloridostannate (IV), C14H18N8O8SnCl6
  33. The crystal structre of 3-(1-ethenyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate, C8H12N2O3S
  34. Synthesis and crystal structure of di-tert-butyl 1″-acetyl-2,2″,9′-trioxo-4a′,9a′-dihydro-1′H,3′H,9′H-dispiro[indoline-3,2′-xanthene-4′,3″-indoline]-1,3′-dicarboxylate, C39H38N2O9
  35. The crystal structure of 4-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  36. The crystal structure of 1-fluoro-4-(p-tolylethynyl)benzene, C15H11F
  37. The crystal structure of bis[4-bromo-2-(1H-pyrazol-3-yl) phenolato-κ2N,O] copper(II), C18H12Br2CuN4O2
  38. The crystal structure of poly[(μ 3-imidazolato-κ 3 N:N:N′)(tetrahydrofuran- κ 1 O)lithium(I)], C7H11LiN2O
  39. Crystal structure of N′,N′′′-((1E,1′E)-(propane-2,2-diylbis(1H-pyrrole-5,2diyl))bis(methaneylylidene))di(nicotinohydrazide) pentahydrate, C25H24N8O2·5H2O
  40. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-ethyl-1H-imidazol-3-ium hexafluoridophos-phate(V), C9H15F6N2O2P
  41. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(3-thiophenecarboxylato-κ2O,O′)copper(II), C22H14N2O4S2Cu
  42. The crystal structure of 2-amino-3-carboxypyridin-1-ium iodide hemihydrate, C6H8IN2O2.5
  43. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-2-yl)methylene)-tetralone, C18H17NO3
  44. The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br
  45. The crystal structure of 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
  46. The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2
  47. Crystal structure of monocarbonyl(N-nitroso-N-oxido-phenylamine-κ 2 O,O′)(tricyclohexylphosphine-κP)rhodium(I), C25H39N2O3PRh
  48. Crystal structure of poly[bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N:N′:N″]nickel(II)] hexafluorosilicate, C36H36N12NiSiF6
  49. The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
  50. Crystal structure of 3,5-bis((E)-4-methoxy-2-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  51. The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
  52. Crystal structure of (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  53. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
  54. The crystal structure of cis-diaqua-bis (N-butyl-N-(pyridin-2-yl)pyridin-2-amine-κ2N,N′)cobalt(II)] dichloride trihydrate, C28H44Cl2N6O5Co
  55. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3
  56. Crystal structure of (E)-2-((3-fluoropyridin-4-yl)methylene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  57. The crystal structure of 6-bromohexanoic acid, C6H11BrO2
  58. The crystal structure of 4-chloro-thiophenol, C6H5ClS
  59. The crystal structure of 4-bromobenzyl chloride, C7H6BrCl
  60. The crystal structure of di-tert-butyl dicarbonate, C10H18O5
  61. The crystal structure of (2-(4-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  62. The crystal structure of the co-crystal: 2-hydroxybenzoic acid – N′-(butan-2-ylidene)pyridine-4-carbohydrazide, C10H13N3O·C7H6O3
  63. Crystal structure and anti-inflammatory activity of (E)-7-fluoro-2-((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  64. Crystal structure of (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  65. Crystal structure of 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C32H56F24N8P4
  66. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2)-cadmium(II), C14H20CdCl2N4O4
  67. Crystal structure of 1-(2-cyanobenzyl)-3-cyano-4-phenyl-4-(2-cyanobenzyl)-1,4-dihydropyridine monohydrate, C56H42N8O
  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 16.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2021-0160/html?licenseType=open-access
Scroll to top button