Home Crystal structure of poly[(μ4-benzene-1,2,4,5-tetracarboxylato)-bis(μ2-adipohydrazide)dicadmium], C11H15N4O6Cd
Article Open Access

Crystal structure of poly[(μ4-benzene-1,2,4,5-tetracarboxylato)-bis(μ2-adipohydrazide)dicadmium], C11H15N4O6Cd

  • Yuhong Long , Xiaoyu Hu and Jingwen Ran ORCID logo EMAIL logo
Published/Copyright: September 8, 2021

Abstract

C11H15CdN4O6, monoclinic, P21/n (no. 14), a = 11.1387(15) Å, b = 10.3933(14) Å, c = 12.2891(17) Å, β = 105.319(2)°, Z = 4, V = 1372.1(3) Å3, Rgt(F) = 0.0286, wRref(F2) = 0.0477, T = 296(2) K.

CCDC no.: 2106207

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 prism
Size: 0.32 × 0.31 × 0.28 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.63 mm−1
Diffractometer, scan mode: Bruker Apex-III, φ and ω
θmax, completeness: 27.0°, 99%
N(hkl)measured, N(hkl)unique, Rint: 7847, 2966, 0.035
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2324
N(param)refined: 200
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 Uiso*/Ueq
Cd1 0.60643 (2) 0.19229 (2) 0.16712 (2) 0.01766 (8)
O1 0.82720 (17) 0.1852 (2) 0.16547 (16) 0.0218 (5)
O2 0.69441 (17) 0.0556 (2) 0.04887 (16) 0.0222 (5)
O3 0.82900 (19) −0.2851 (2) 0.04777 (18) 0.0282 (5)
O4 0.85391 (19) −0.15641 (19) 0.19838 (17) 0.0254 (5)
O5 0.43704 (19) 0.0986 (2) 0.22782 (19) 0.0316 (6)
O6 0.12613 (19) 0.1328 (2) 0.54508 (17) 0.0288 (5)
N1 0.5739 (2) −0.0581 (3) 0.3011 (2) 0.0290 (7)
H1 0.586555 −0.133593 0.330668 0.035*
N2 0.6746 (2) 0.0170 (2) 0.2884 (2) 0.0251 (6)
H2A 0.725321 −0.031738 0.260864 0.030*
H2B 0.717310 0.045954 0.355689 0.030*
N3 −0.0373 (2) 0.2228 (3) 0.4215 (2) 0.0279 (7)
H3A −0.081536 0.229573 0.352884 0.033*
N4 −0.0665 (2) 0.2965 (3) 0.5080 (2) 0.0269 (6)
H4A −0.130412 0.260780 0.527426 0.032*
H4B −0.088622 0.375532 0.482705 0.032*
C1 0.8026 (3) 0.0981 (3) 0.0910 (2) 0.0172 (7)
C2 0.9070 (2) 0.0450 (3) 0.0478 (2) 0.0137 (6)
C3 0.9776 (3) 0.1300 (3) 0.0027 (2) 0.0161 (6)
H3 0.962917 0.217875 0.005232 0.019*
C4 0.9307 (2) −0.0869 (3) 0.0459 (2) 0.0137 (6)
C5 0.8648 (2) −0.1853 (3) 0.1000 (2) 0.0185 (6)
C6 0.4586 (3) −0.0109 (3) 0.2668 (3) 0.0251 (7)
C7 0.3576 (3) −0.1045 (3) 0.2747 (3) 0.0388 (9)
H7A 0.383275 −0.147862 0.347062 0.047*
H7B 0.350671 −0.169223 0.216551 0.047*
C8 0.2300 (3) −0.0464 (3) 0.2629 (3) 0.0322 (9)
H8A 0.209268 0.007089 0.195782 0.039*
H8B 0.169497 −0.115533 0.251406 0.039*
C9 0.2176 (3) 0.0338 (3) 0.3620 (3) 0.0288 (8)
H9A 0.264359 0.112985 0.364786 0.035*
H9B 0.252117 −0.013060 0.431484 0.035*
C10 0.0814 (3) 0.0653 (3) 0.3518 (3) 0.0274 (8)
H10A 0.048202 0.112498 0.282297 0.033*
H10B 0.035221 −0.014663 0.346518 0.033*
C11 0.0599 (3) 0.1426 (3) 0.4480 (3) 0.0205 (7)

Source of material

The reagents were purchased from commercial sources and used without further purification.

A mixture of benzene-1,2,4,5-tetracarboxylic acid (0.25 mmol, 63.5 mg), NaOH (1.0 mmol, 40 mg) and deionized water (5 mL) was placed in a high-pressure resistant glass bottle (10 mL), the bottle was sealed and heated at 353 K for 30 min. After that, cadmium acetate dihydrate (0.5 mmol, 133 mg) and adipohydrazide (0.5 mmol, 87 mg) were added, and the bottle was sealed and heated at 393 K for 24 h and cooled to room temperature. Colorless prism crystals were obtained by filtration, washed with deionized water and dried in air. Yield 46% based on Cd(II).

Experimental details

H atoms were added using riding models. Their Uiso values were set to 1.2Ueq of the parent atoms.

Comment

Researchers have focused on coordination polymers due to their versatile architecture and potential applications for luminescent properties, magnetic interactions, catalytic ability, and so on [5, 6]. As a versatile ligand benzene-1,2,4,5-tetracarboxylate has been widely used to construct transition metal or rare earth metal complexes using its multiple coordination function modes.

The asymmetric unit of the complex consists of one Cd ion, one adipohydrazide ligand and one half of a fully deprotonated benzene-1,2,4,5-tetracarboxylate (btc4−). The btc4− ligand is located on a center of inversion (see the Figure). The central Cd ion is coordinated by a chelating carboxylate group (O1 and O2) and a monodentate carboxylate group (O4) from two btc4− ligands. In addition, two adipohydrazide ligands provide two oxygen atoms (O5 and O6) and two nitrogen atoms (N2 and N4) to coordinate with the central cadmium ion, forming a distorted single capped octahedron. Each Cd ion is connected by two btc4− ligands to form a two-dimensional network with a rhombic-shaped grid [7]. The adipohydrazide ligands are interspersed in the two-dimensional structure, ensuring the Cd ion to form a seven-coordinated conformation, enhancing the stability of the coordination polymer. The Cd–O bond distances fall in the range of 2.239(2)–2.4646 (19) Å and the Cd–N bond distances are 2.349(2) and 2.356(2) Å. All the bond lengths around the Cd1 center are within the normal range [8, 9]. The N–N bond distances are 1.410(3) and 1.415(3) Å, which are in good agreement with the reported information [10, 11].


Corresponding author: Jingwen Ran, Hubei Key Laboratory for Processing and Application of Catalytic Materials, College of Chemistry and Chemical Engineering, Huanggang Normal University, Huanggang 438000, China, E-mail:

Funding source: Hubei Provincial Central Committee Guiding Local Science and Technology Development Project

Award Identifier / Grant number: 2019ZYYD074

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

  2. Research funding: This work was supported by Hubei Provincial Central Committee Guiding Local Science and Technology Development Project (No. 2019ZYYD074).

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

References

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

2. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/S2053273314026370.Search in Google Scholar PubMed PubMed Central

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 PubMed PubMed Central

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

5. Zhou, Y., Yoon, J. Recent progress in fluorescent and colorimetric chemosensors for detection of amino acids. Chem. Soc. Rev. 2012, 41, 52–67; https://doi.org/10.1039/c1cs15159b.Search in Google Scholar PubMed

6. Dhakshinamoorthy, A., Garcia, H. Catalysis by metal nanoparticles embedded on metal-organic frameworks. Chem. Soc. Rev. 2012, 41, 5262–5284; https://doi.org/10.1039/c2cs35047e.Search in Google Scholar PubMed

7. Shi, R., Zhu, X., Lin, S. Y., Su, Y. Y., Zhang, S. Y. Crystal structure of poly[aqua-(μ4-benzene-1,2,4,5-tetracarboxylato-bis[μ2-1(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazol-dinickel(II)], NiC17H14N5. Z. Kristallogr. N. Cryst. Struct. 2020, 235, 817–819; https://doi.org/10.1515/ncrs-2020-0027.Search in Google Scholar

8. Cai, H., Xu, C., Zhou, Y. P., Tong, X. Q., Guo, Y. Molecular tectonics of mixed-ligand metal-organic frameworks: positional isomeric effect, and structural diversification. J. Mol. Struct. 2016, 1108, 263–268; https://doi.org/10.1016/j.molstruc.2015.12.006.Search in Google Scholar

9. Lin, J. D., Cheng, J. W., Du, S. W. Five d10 3D metal-organic frameworks constructed from aromatic polycarboxylate acids and flexible imidazole-based ligands. Cryst. Growth Des. 2008, 8, 3345–3353; https://doi.org/10.1021/cg8002614.Search in Google Scholar

10. Lo, K. M., Lee, S. M., Tiekink, E. R. T. Crystal structure of heanedihydrazide, C6H14N4O2. Z. Kristallogr. N. Cryst. Struct. 2020, 235, 1257–1258; https://doi.org/10.1515/ncrs-2020-0301.Search in Google Scholar

11. Zabierowski, P., Oszajca, M., Hodorowicz, M., Matoga, D. Ladder-chain zinc coordination polymers based on adipic acid dihydrazide precursor: synthesis and structural transformations. Polyhedron 2017, 121, 25–36; https://doi.org/10.1016/j.poly.2016.09.053.Search in Google Scholar

Received: 2021-07-29
Accepted: 2021-08-29
Published Online: 2021-09-08
Published in Print: 2021-12-20

© 2021 Yuhong Long 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. Redetermination of the crystal structure of 3-bromonitrobenzene at 200 K, C6H4BrNO2 – temperature effects on cell constants
  4. Crystal structure of (E)-ethyl 2-((4-oxo-4H-chromen-3-yl)methyleneaminooxy)acetate, C14H13NO5
  5. Crystal structure of (8R,10R,14R, Z)-2-((3–Fluoropyridin-4-yl) methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6, 6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a] phenanthren-3-one, C36H52FNO3
  6. Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-κ4N,N′,O,O′] copper(II), C17H14Cl2CuN2O2
  7. The crystal structure of 6-amino-2-carboxypyridin-1-ium bromide, C6H7BrN2O2
  8. Redetermination of the crystal structure of bis[N,N′-ethylenebis(acetylacetoniminato)nickel(II)] sodium perchlorate, C24H36ClN4NaNi2O8
  9. The crystal structure of 3-methyl-2,6-dinitrophenol, C7H6N2O5
  10. The crystal structure of 5-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  11. Crystal structure of trans-tetraaqua-bis{2-carboxy-4-((5-carboxypyridin-3-yl)oxy)benzoato-κ1 N}cobalt(II) dihydrate C28H28O20N2Co
  12. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-(p-tolyl)furan, C23H23BrO2
  13. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(benzo[d][1,3]dioxol-5-ol ato-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV)-dichloromethane(1/1), C27H25N3O10Ti
  14. Crystal structure of (((1E,1′E)-1,2-phenylenebis(methaneylylidene))bis(hydrazin-1-yl-2-ylidene))bis(aminomethaniminium) dinitrate C10H16N10O6
  15. Crystal structure of catena-poly[triaqua-(μ 2-1,3-di(1H-imidazol-1-yl)propane-κ 2 N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ 1 O)nickel(II)]N,N′-dimethylformamide (1/1), C28H35N8O8Ni
  16. The crystal structure of 3,3′-[1,4-phenylenebis(methylene)]bis(1-ethenyl-1H-imidazol-3-ium) dichloride – dichloromethane – water (1/1/1), C19H24Cl4N4O1
  17. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C13H22F12N4P2
  18. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)tin(IV), C12H8Cl4Sn
  19. Synthesis and crystal structure of 4-acetylpyrene, C18H12O
  20. Crystal structure of 2,2′-(butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(4-methoxyphenol), C20H24N2O4
  21. The crystal structure of (E)-2-(((5-((triphenylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C27H21N3OS2Sn
  22. Crystal structure of diaqua-bis(μ2-6-phenylpyridine-2-carboxylate-κ3N,O:O)-bis(6-phenylpyridine-2-carboxylato-κ2N,O)lead(II) – N,N-dimethylformamide – water (1/2/4), C54H58N6O16Pb2
  23. Crystal structure of methyl 4-acetoxy-3-methoxybenzoate, C11H12O5
  24. Crystal structure of 2,2′-(propane-1,3-dilylbis(azaneylylidene))bis(methanylylidene)bis(4-methylphenol), C19H22N2O2
  25. Crystal structure of dichlorido-bis(4-methylphenyl-κC1)tin(IV), C14H14Cl2Sn
  26. Crystal structure of methyl (E)-3-(4-acetoxyphenyl)acrylate, C12H12O4
  27. The crystal structure of bis(benzoato-κ2 O,O′)-(2,9-dimethyl-1,10-phenanthroline-κ2 N,N′)-copper(II), C28H22CuN2O4
  28. Crystal structure of (8R,10R,14R,Z)-12-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one–water (2/1), C37H56NO4.5
  29. Crystal structure of dimethyl-bis(4-bromophenyl-κC1)tin(IV), C14H14Br2Sn
  30. The crystal structure of the cocrystal di-μ2-chlorido-octamethyl-di-μ3-oxido-bis(2,3,4,5-tetrafluorobenzoato-κ2 O,O′)tetratin(IV) ─ octamethyl-di-μ3-oxido-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O′)-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O;O′)tetratin(IV) C58H54Cl2F24O16Sn8
  31. Crystal structure of 3-iodo-N 2-(2-methyl-1-(methylsulfonyl)propan-2-yl)-N 1-(2-methyl-4-(perfluoropropan-2-yl)phenyl)phthalamide, C23H22F7I1N2O4S1
  32. Crystal structure of 1-(2-(4-bromophenyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)-naphthalen-2-ol – dichloromethane – dimethyl sulfoxide (1/1/1), C28H18BrNO·CH2Cl2·C2H6SO
  33. Crystal structure of [meso-5,7,7,12,14,14,-hexamethyl-1,4,8,11-tetraazacyclotetradecane]nickel(II) diperchlorate – dimethylsulphoxide (1/2), C20H48Cl2N4NiO10S2
  34. Crystal structure of 1,1′-(1,3-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S) palladium(II), C26H18N6PdS4
  35. The crystal structure of bis(6-phenylpyridine-2-carboxylato-κ2 N,O)copper(II), C24H16N2O4Cu
  36. Crystal structure of dichlorido-bis(4-chlorophenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C48H38As2Cl4O2Sn
  37. Crystal structure of (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane-κ 8 N 2, O 6) potassium cyclopentadienide, [K([2.2.2]crypt)]Cp, C23H41KN2O6
  38. The crystal structure of bis(2-oxidopyridin-1-ium-3-carboxylato-κ2O,O′)-(phenantroline-κ2N,N′)manganese(II) - methanol (1/3), C27H28N4O9Mn
  39. Crystal structure of 4-(dimethylamino)pyridinium dibromido-tris(4-chlorophenyl-κC)stannate(IV), C25H23Br2Cl3N2Sn
  40. Crystal structure of (3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis(3-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C27H20Cl2F2N2O3S
  41. Crystal structure of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-trifluoromethyl)benzenesulfonyl)piperidin-4-one, C26H18F5NO3S
  42. Crystal structure of chlorido-(4-methyl-2-((phenylimino)methyl)phenolato-κ2 N,O)-(pyridine-κ1 N)platinum(II), C19H17ClN2OPt
  43. Crystal structure of (4-methylbenzyl)(triphenyl)phosphonium chloride dihydrate, C26H28ClO2P
  44. The crystal structure of poly[μ2-chlorido-(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′silver(I)], C12H12AgClN2
  45. Crystal structure of poly[(μ4-benzene-1,2,4,5-tetracarboxylato)-bis(μ2-adipohydrazide)dicadmium], C11H15N4O6Cd
  46. The crystal structure of (E)-N′-(butan-2-ylidene)isonicotinohydrazide 0.5 hydrate C10H13N3O·0.5H2O
  47. The crystal structure of bis(6-phenylpyridine-2-carboxylate-κ2 N,O)-(2,2′-bipyridine-κ2 N,N′)zinc(II) monohydrate, C34H26N4O5Zn
  48. The crystal structure of (1R *,2S *)-1,2-bis(2-fluorophenyl)-3,8-dimethoxyacenaphthene-1,2-diol, C26H20F2O4
  49. Crystal structure of catena-poly[(μ2-1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzotriazole-κ2N:N′)-(nitrato-κ2O,O′)silver (I)], C13H15Ag1N6O3
  50. The crystal structure of [(phenantroline-κ2 N,N′)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)cobalt(II)]monohydrate, C36H26N4O5Co
  51. Crystal structure of (1E)-N-[(1E)-1-(4-chlorophenyl)ethylidene]-2-[1-(4-chlorophenyl)ethylidene]hydrazine-1-carbohydrazonamide, C 17 H 17 Cl 2 N 5
  52. The crystal structure of (E)-2-((tert-butylimino)methyl)-4-chlorophenol, C11H14ClNO
  53. Crystal structure of all-cis-2,4,6-trihydroxycyclohexane- 1,3,5-triaminium chloride sulfate, C6H18ClN3O7S
  54. Crystal structure of dichlorido-bis(dimethyl sulfoxide-κO)bis(4-methylphenyl-κC 1)tin(IV), C18H26Cl2O2S2Sn
  55. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)(2,2′-bipyridyl-κ 2 N,N′)tin(IV), C22H16Cl4N2Sn
  56. Redetermination of the crystal structure of (E)-5-bromo-2-hydroxybenzaldehyde oxime, C 7 H 6 BrNO 2
  57. The crystal structure of (E)-amino(2-(4-methylbenzylidene)hydrazineyl)methaniminium 4-methylbenzoate, C9H13N4 + C8H7O2
  58. Crystal structure of 2-chloro-3-(isopentylamino)naphthalene-1,4-dione, C 15 H 16 ClNO 2
  59. The crystal structure of bis(2-acetyl-5-methoxyphenyl)carbonate 1.5 hydrate, C19H18O7
  60. The crystal structure of poly[(μ 4-4,4′-(azanediylbis(methylene))dibenzoato-κ 4 O:N:O′:Oʺ)zinc(II)], C16H13NO4Zn
  61. The crystal structure of catena-poly[(1,10-phenanthroline-k2N,N′)-(μ3-tetraoxidomoybdato(VI)-k3O:O′:O″)manganese(II)] C12H8N2O4MoMn
  62. Crystal structure of catena-poly[(4-hydroxyl-5-(methoylcarbonyl)thiophene-2-carboxylato-κ1 O)-(μ2-piperazine-1,4-diylbis(pyridin-4-ylmethanone)-κ2 N:N′)silver(I)] monohydrate, C23H23AgN4O8S
  63. Crystal structure of bis(4-bromo-2-(((3-bromopropyl)imino)methyl)phenolato-κ2N,O)-oxido-vanadium(IV), C20H20Br4N2O3V
  64. The crystal structure of (2a′S,2a1′S,3R,5a′S,7′R)-5-(furan-3-yl)-2a′,2a1′-dihydroxy-7′-methyldecahydro-2H-spiro[furan-3,6′-naphtho[1,8-bc]furan]-2,2′(2a′H)-dione, C19H22O7
  65. The crystal structure of 3-bromopicolinic acid, C6H4BrNO2
  66. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S,S) platinum(II), C26H18N6PtS4
  67. Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
  68. The crystal structure of 3-amino-5-carboxypyridin-1-ium bromide, C6H7BrN2O2
  69. The crystal structure of (2-hydroxy-5-methyl-phenyl)-(1H-pyrazol-4-yl)-methanone hemihydrate, C11H10.5N2O2.5
  70. Crystal structure of tetraaqua-(2-(4-formylphenoxy)acetato-k1O)cadmium(II), C18H22O12Cd
  71. Crystal structure of diethyl 6,12-dimethyl-3,9-di-p-tolyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5-dicarboxylate, C32H38N2O4
  72. Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5
Downloaded on 16.11.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2021-0309/html?lang=en
Scroll to top button