Home Crystal structure of catena-poly[(benzylamine-κ1 N)-(sorbato-κ1 O)-(μ2-sorbato-κ2 O,O′)-copper(II), C19H23CuNO4
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Crystal structure of catena-poly[(benzylamine-κ1 N)-(sorbato-κ1 O)-(μ2-sorbato-κ2 O,O′)-copper(II), C19H23CuNO4

  • Hyewon Shin , Jaeun Kang , Kang Min Ok and Junghwan Do ORCID logo EMAIL logo
Published/Copyright: March 12, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 3

Abstract

C19H23CuNO4, monoclinic, C2/c (no. 15), a = 16.1601(4) Å, b = 23.3298(7) Å, c = 12.8950(3) Å, β = 128.275(1)∘, V = 3816.6(2) Å3, Z = 8, R gt(F) = 0.0620, wR ref(F 2) = 0.1251, T = 296(2) K.

CCDC no.: 2334463

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: Blue polyhedron
Size: 0.28 × 0.25 × 0.19 mm
Wavelength:

μ:		 Mo Kα radiation (0.71073 Å)

1.17 mm−1
Diffractometer, scan mode:

θ max, completeness:		 Bruker P4, ω

28.3°, >99 %
N(hkl)measured, N(hkl)unique, R int: 24932, 4722, 0.145
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2646
N(param)refined: 228
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
Cu1 0.36860 (3) 0.26536 (2) 0.14511 (4) 0.03431 (16)
O1 0.4099 (2) 0.31020 (11) 0.0558 (2) 0.0422 (7)
O2 0.42021 (19) 0.32727 (11) 0.2742 (3) 0.0404 (7)
C1 0.4949 (3) 0.33785 (16) 0.1120 (4) 0.0349 (9)
C2 0.4991 (3) 0.38642 (17) 0.0420 (4) 0.0440 (10)
H2 0.561108 0.407615 0.086975 0.053*
C3 0.4213 (3) 0.40163 (17) −0.0792 (4) 0.0465 (11)
H3 0.359005 0.380818 −0.122096 0.056*
C4 0.4232 (4) 0.4478 (2) −0.1527 (5) 0.0603 (13)
H4 0.483442 0.470496 −0.108956 0.072*
C5 0.3455 (4) 0.4601 (2) −0.2774 (5) 0.0694 (15)
H5 0.284827 0.437928 −0.318749 0.083*
C6 0.3447 (5) 0.5055 (2) −0.3587 (6) 0.101 (2)
H6A 0.405135 0.529782 −0.303092 0.151*
H6B 0.281627 0.527976 −0.401105 0.151*
H6C 0.346737 0.488140 −0.424603 0.151*
O3 0.31230 (19) 0.20464 (11) 0.0120 (2) 0.0366 (6)
O4 0.4752 (2) 0.17689 (13) 0.1019 (3) 0.0720 (11)
C7 0.3791 (3) 0.17181 (17) 0.0176 (4) 0.0403 (10)
C8 0.3339 (3) 0.12689 (16) −0.0860 (4) 0.0410 (10)
H8 0.260976 0.124972 −0.149215 0.049*
C9 0.3920 (3) 0.08925 (17) −0.0933 (4) 0.0460 (11)
H9 0.464811 0.093243 −0.032918 0.055*
C10 0.3516 (4) 0.04277 (17) −0.1868 (4) 0.0475 (11)
H10 0.278856 0.039062 −0.249044 0.057*
C11 0.4112 (4) 0.00508 (18) −0.1900 (4) 0.0541 (12)
H11 0.483799 0.010213 −0.130794 0.065*
C12 0.3707 (4) −0.0452 (2) −0.2815 (5) 0.0746 (16)
H12A 0.401133 −0.079774 −0.230943 0.112*
H12B 0.389766 −0.041001 −0.338428 0.112*
H12C 0.295399 −0.046976 −0.333943 0.112*
N1 0.3191 (2) 0.21851 (13) 0.2272 (3) 0.0377 (8)
H1A 0.261187 0.200107 0.162156 0.045*
H1B 0.368019 0.191957 0.277150 0.045*
C13 0.2956 (5) 0.2459 (2) 0.3076 (6) 0.0802 (17)
H13A 0.235316 0.270851 0.250948 0.096*
H13B 0.355026 0.269946 0.372336 0.096*
C14 0.2724 (4) 0.20676 (19) 0.3799 (5) 0.0543 (12)
C15 0.1742 (4) 0.2027 (2) 0.3446 (5) 0.0619 (13)
H15 0.119044 0.222746 0.271164 0.074*
C16 0.1546 (5) 0.1691 (2) 0.4162 (6) 0.0787 (16)
H16 0.086625 0.166663 0.390169 0.094*
C17 0.2340 (6) 0.1400 (3) 0.5236 (6) 0.0814 (18)
H17 0.220845 0.118046 0.572185 0.098*
C18 0.3327 (5) 0.1428 (2) 0.5606 (6) 0.0831 (18)
H18 0.387189 0.122438 0.634046 0.100*
C19 0.3525 (5) 0.1759 (2) 0.4893 (6) 0.0748 (16)
H19 0.420464 0.177541 0.515035 0.090*

1 Source of material

The mixture of CuCl (0.030 g, 0.3 mmol), benzylamine (0.033 mL, 0.3 mmol), sorbic acid (0.034 g, 0.3 mmol) in ethanol (1.0 mL) was sealed under vacuum in a Pyrex tube and heated to 70 °C for 68 h, then cooled to room temperature at 20 °C/h. The pH before the reaction was 6 and it remained unchanged after the reaction. The blue polyhedral crystals of the title compound were recovered by vacuum filtration. The product is stable in air.

2 Experimental details

All hydrogen atoms were placed in calculated positions and refined as riding model, and their positions and isotropic displacement parameters were refined. The Uiso value of the H atoms in sorbate and benzylamine were set to 1.2 Ueq except for the terminal methyl group (1.5 Ueq) in sorbate.

3 Comment

Many copper(II) complexes have been studied because of their interesting structural features followed by the metal center being able to adopt various coordination geometries such as square planar, square pyramidal, trigonal bipyramidal, and octahedral [5]. Specially, copper(II) carboxylates containing nitrogen donor ligands have been extensively studied due to their importance in biology and magnetism [6], [7], [8], [9]. In this study we report a 1D copper(II) coordination polymer containing monocarboxylic sorbate anion and benzylamine molecule.

One unique copper atom is coordinated by each one oxygen atoms of three sorbate anions (d(Cu–O) = 1.954(3), 1.958(2), 1.961(2) Å) and one nitrogen atom of benzylamine (d(Cu–N) = 2.001(3) Å) to form a square planar geometry. An additional sorbate oxygen atom is weakly coordinated to Cu in an apical position (d(Cu–O) = 2.409(2) Å), completing the slightly distorted square pyramidal arrangement, as evidenced by the τ value (angular structure parameter) of 0.02 [10]. The bond valence sum (BVS) calculation for Cu gives a value of +2.024 indicating an oxidation state of +2 [11]. The CuNO4 square pyramids share a common edge of weakly bonded oxygen (O3) atoms to form Cu2N2O6 dimeric units with the Cu⋯Cu distance of about 3.38 Å. The dinuclear Cu(II) unit is positioned around a center of inversion. The dimers are connected to each other by sorbate anions, forming a neutral Cu(benzylamine) (sorbate)2 chain in the [101] direction. The chains are further stabilized by the presence of intra-chain hydrogen bonds between the NH2 of benzylamine and non-coordinated carboxylate O atom [d(NH⋯O4) = 2.788(4) Å] or the coordinated carboxylate O atom [d(NH⋯O3) = 2.727(4) Å]. That is, of the two independent sorbates, only one sorbate weakly coordinated with Cu is involved in the hydrogen bonds. Adjacent chains are arranged so that the alkyl group of sorbates are partially interdigitated. The interchain distance between the sorbate groups is >3.78 Å, suggesting that van der Waals interactions predominate with only weak π–π stacking.

Corresponding author: Junghwan Do, Department of Chemistry, Konkuk University, Seoul 05029, Republic of Korea, E-mail:

Funding source: (NRF) grant funded by the Korea government (MSIT)

Award Identifier / Grant number: (No. 2021R1F1A1060277)

Acknowledgments

This work was supported by the (NRF) grant funded by the Korea government (MSIT) (No. 2021R1F1A1060277).

  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: (NRF) grant funded by the Korea government(MSIT) (No. 2021R1F1A1060277).

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Received: 2024-01-05
Accepted: 2024-02-22
Published Online: 2024-03-12
Published in Print: 2024-06-25

© 2024 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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https://doi.org/10.1515/ncrs-2024-0005
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of tris((Z)-2-hydroxy-N-((E)-pyridin-2-ylmethylene)benzohydrazonato-k2O,N)europium(III), C39H30N9O6Eu
  4. Crystal structure of (E)-3-(benzylideneamino)-2-phenylthiazolidin-4-one, C16H14N2OS
  5. The crystal structure of (E)-4-fluoro-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H15FN2O
  6. Crystal structure of (6-chloropyridin-3-yl)methyl 2-(6-methoxynaphthalen-2-yl)propanoate, C20H18ClNO3
  7. Crystal structure of methyl 3-methoxy-4-(2-methoxy-2-oxoethoxy)benzoate, C12H14O6
  8. The crystal structure of bis[(4-methoxyphenyl)(picolinoyl)amido-κ2 N:N′]copper(II), C26H22CuN4O4
  9. The crystal structure of poly[di(μ2-aqua)-diaqua-bis(3-aminopyridine-4-carboxylate-κ2 O: O′)-tetra(μ2-3-aminopyridine-4-carboxylate-κ2 O: O′)-dineodymium(III), [Nd2(C6H5N2O2)6(H2O)4] n
  10. The crystal structure of t-butyl 7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate, C28H34FNO4
  11. Crystal structure of catena-poly[(benzylamine-κ1 N)-(sorbato-κ1 O)-(μ2-sorbato-κ2 O,O′)-copper(II), C19H23CuNO4
  12. Crystal structure of (4-(2-chlorophenyl)-1H-pyrrol-3-yl)(ferrocenyl) methanone, C21H16ClFeNO
  13. The crystal structure of N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-3-(2-methylphenyl)-2-sulfanylprop-2-enamide hydrate, C19H17BrN2O2S2
  14. The crystal structure of N′-{5-[2-(2,6-dimethylphenoxy) acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl}-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide hydrate
  15. Crystal structure of 2-(naphthalen-1-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C26H24O3
  16. Crystal structure of naphthalen-1-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C25H22O3
  17. Crystal structure of poly[diaqua- (μ4-5-(1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ5N:O,O’:O’’:O’’’)calcium(II), C10H9CaN3O6
  18. Crystal structure of (E)-N′-(4-((E)-3-(dimethylamino)acryloyl)-3-hydroxyphenyl)-N, N-dimethylformimidamide, C14H19N3O2
  19. Crystal structure of (E)-3-(dimethylamino)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one, C13H17NO4
  20. Crystal structure of (2-chloropyridin-3-yl)methyl-2-(6-methoxynaphthalen-2-yl)propanoate, C20H18ClNO3
  21. The crystal structure of diethyl 4-(3,4-dimethylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C21H27NO4
  22. Crystal structure of (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-17-((4-(2-phenylpropyl)phenyl)ethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H42O2
  23. Synthesis and crystal structure of 4-(4-cyclopropylnaphthalen-1-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, C15H13N3S
  24. Crystal structure of catena-poly[aqua-(2,6-di-(2-pyridyl)-pyridine-κ3 N,N′, N″)(μ2-1,4-naphthalene dicarboxylato-κ2 O,O′)nickel(II)], C27H19NiN3O5
  25. Crystal structure of 3-(diphenylphosphoryl)-3-hydroxy-1-phenylpropan-1-one, C21H19O3P
  26. The crystal structure of R,S-{N-[(2-oxidonaphthalen-1-yl)methylidene]phenylglycinato}divinylsilicon, C23H19NO3Si
  27. The crystal structure of 1,2,4-tris(bromomethyl)benzene, C9H9Br3
  28. Crystal structure of chlorido-[4-(pyridin-2-yl)benzaldehyde-κ2 N,C]-(diethylamine-κ1 N)platinum(II), C16H18ClN2OPt
  29. Crystal structure of 3-(methoxycarbonyl)-1-(4-methoxyphenyl)-2,3,4,9- tetrahydro-1H-pyrido[3,4-b]indol-2-ium chloride hydrate, C40H48Cl2N4O9
  30. The crystal structure of 1-(2-chlorobenzyl)-3-(3-chlorophenyl)urea, C14H12Cl2N2O
  31. Hydrothermal synthesis and crystal structure of aqua-tris(4-acetamidobenzoato-κ2 O,O′)-(1,10-phenanthroline-κ2 N,N′)terbium(III) hydrate C39H36N5O11Tb
  32. The crystal structure of zwitterionic 3-aminoisonicotinic acid, C6H6N2O2
  33. The crystal structure of bis{[monoaqua-μ2-4-[(pyridine-4-carbonyl)-amino]-phthalato-κ3 N:O,O′-(2,2′-bipyridine κ2 N,N′)copper(II)]}decahydrate, C48H56N8O22Cu2
  34. Crystal structure of poly[μ10-4,4′-methylene-bis(oxy)benzoatodipotassium], C15H10K2O6
  35. The crystal structure of catena-poly[[tetraaqua[(μ2-1,4-di(4-methyl-1-imidazolyl)benzene] cobalt(II)]bis(formate)], C16H24CoN4O8
  36. The crystal structure of (E)-2-chloro-5-((2-(nitromethylene)imidazolidin-1-yl)methyl)pyridine, C10H11ClN4O2
  37. The crystal structure of (E)-1-(((2-amino-4,5-dimethylphenyl)iminio)methyl)naphthalen-2-olate, C19H18N2O
  38. Crystal structure of N-(acridin-9-yl)-2-(4-methylpiperidin-1-yl) acetamide monohydrate, C21H25N3O2
  39. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2 O,O′)-zinc(II), C14H20Cl2N4O4Zn
  40. The crystal structure of 2,8-diethyl-1,3,7,9-tetramethyl-4λ4,5λ4-spiro[dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine-5,2′-naphtho[1,8-de][1,3,2]dioxaborinine], C25H29BN2O2
  41. The crystal structure of 5-tert-butyl-2-(5-tert-butyl-3-iodo-benzofuran-2-yl)-3-iodobenzofuran, C24H24I2O2
  42. Synthesis and crystal structure of methyl 2-{[4-(4-cyclopropyl-1-naphthyl)-4H-1,2,4-triazole-3-yl]thio} acetate, C18H17N3O2S
  43. The crystal structure of n-propylammonium bis(2,3-dimethylbutane-2,3-diolato)borate-boric acid (1/1), [C3H10N][C12H24BO4]·B(OH)3
  44. Crystal structure of methyl 1-(2-bromophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C19H17BrN2O2
  45. Crystal structure of (4-bromobenzyl)triphenylphosphonium bromide ethanol solvate, C52H48Br4OP2
  46. The crystal structure of unsymmetrical BOPHY C26H27BN4
  47. The crystal structure of Tb3B5O11(OH)2
  48. The crystal structure of (Z)-4-ethyl-2-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3,5-dimethyl-2H-pyrrol-1-ium 2,2'-spirobi[naphtho[1,8-de][1,3,2]dioxaborinin]-2-uide, C37H37BN2O4
  49. Crystal structure of bis(methylammonium) hexadecaselenidopalladate(II), (CH3NH3)2PdSe16
  50. The crystal structure of (2-diphenylphosphanylphenyl) 2-[7-(dimethylamino)-2-oxochromen-4-yl]acetate, C31H26NO4P
  51. Crystal structure of (E)-6-(4-ethylpiperazin-1-yl)-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C23H25FN2O
  52. The structure of RUB-56, (C6H16N)8 [Si32O64(OH)8]·32 H2O, a hydrous layer silicate (2D-zeolite) that contains microporous levyne-type silicate layers
  53. Crystal structure of 4-amino-3,5-dibromobenzonitrile, C7H4Br2N2
  54. Crystal structure of 2-(naphthalen-1-yl)ethyl 2-acetoxybenzoate, C21H18O4
  55. Single-crystal structure determination of Tm3B12O19(OH)7
  56. Crystal structure determination of NdB3.6O7
  57. The crystal structure of NdB6O8(OH)5·H3BO3
  58. Crystal structure of 2-(5-ethylpyridin-2-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H25NO3
  59. Crystal structure of N-(1-(3,4-dimethoxyphenyl)-2-methylpropyl)aniline, C18H23NO2
  60. Crystal structure of Ba6Cd12Mn4SiF48
  61. Synthesis and crystal structure of 5-fluoro-1-methyl-2-oxo-3-(2-oxochroman-4-yl)indolin-3-yl acetate, C20H16FNO5
  62. The crystal structure of 6-methacryloylbenzo[d][1,3]dioxol-5-yl 4-nitrobenzenesulfonate, C17H13NO8S
  63. Crystal structure of ethyl 2-(3-benzyl-4-oxo-3,4-dihydrophthalazin-1-yl)- 2,2-difluoroacetate, C19H16F2N2O3
  64. The crystal structure of tetrakis(μ 2-(1H-benzimidazole-2-methoxo-κ2 N,O:O:O)-(n-butanol-κO)-chlorido)-tetranickel(II), C48H68Cl4N8O8Ni4
  65. Synthesis and crystal structure of trans-tetraaqua-bis((1-((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carbonyl)oxy-κO)zinc(II)hexahydrate, C46H64N2O28S2Zn
  66. The crystal structure of 1-(4-carboxybutyl)-3-methyl-1H-imidazol-3-ium hexafluoridophosphate, C9H15F6N2O2P
  67. Crystal structure of 1-(4-chlorophenyl)-4-(2-furoyl)-3-phenyl-1H-pyrazol-5-ol, C20H13ClN2O3
  68. Crystal structure of dimethyl (R)-2-(3-(1-phenylethyl)thioureido)-[1,1′-biphenyl]-4,4′-dicarboxylate, C25H24N2O4S
  69. The crystal structure of 1-(3-carboxypropyl)-1H-imidazole-3-oxide, C7H10N2O3
  70. Synthesis and crystal structure of dimethyl 4,4′-(propane-1,3-diylbis(oxy))dibenzoate, C19H20O6
  71. Crystal structure of methyl-1-(p-tolyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C20H20N2O2
  72. The crystal structure of 1-(1-adamantan-1-yl)ethyl-3-(3-methoxyphenyl)thiourea, C20H28N2OS
  73. The crystal structure of N,N′-carbonylbis(2,6-difluorobenzamide), C15H8F4N2O3
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