Home Physical Sciences The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
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The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14

  • Hai-Ping Wang ORCID logo EMAIL logo , Ci-Mao Zhang , Guo-Peng Huang and Jia-Jun Liang
Published/Copyright: July 5, 2023

Abstract

C40H39SmN8O14, triclinic, P1̄ (no. 2), a = 8.2799(1) Å, b = 16.6666(5) Å, c = 17.1471(3) Å, α =  73.549 ( 2 ) , β =  89.123 ( 1 ) , γ = 83.045(2)°, V = 2252.2(1) Å3, Z = 2, R g t (F) = 0.0592, w R r e f (F2) = 0.1438, T = 297.71(13) K.

CCDC no.: 2240008

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 needle
Size: 0.15 × 0.14 × 0.12 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 10.4 mm−1
Diffractometer, scan mode: XtaLAB Synergy, ω
θmax, completeness: 74.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 29937, 8756, 0.097
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 7434
N(param)refined: 571
Programs: SHELX [1, 2], Olex2 [3]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.5067 (17) −0.0566 (7) 0.3997 (7) 0.124 (4)
H1A 0.489595 −0.103630 0.380329 0.186*
H1B 0.436067 −0.055043 0.444319 0.186*
H1C 0.617914 −0.062362 0.417619 0.186*
C2 0.4704 (14) 0.0231 (6) 0.3328 (6) 0.091 (3)
H2A 0.526909 0.018336 0.284008 0.109*
H2B 0.354439 0.034516 0.320499 0.109*
C3 0.4806 (10) 0.1683 (5) 0.3125 (4) 0.0653 (19)
C4 0.5388 (8) 0.2342 (5) 0.3443 (4) 0.0576 (17)
C5 0.6399 (8) 0.2146 (5) 0.4132 (4) 0.0589 (17)
H5 0.679018 0.158738 0.438771 0.071*
C6 0.6819 (8) 0.2775 (5) 0.4435 (4) 0.0566 (17)
H6 0.749146 0.263555 0.489508 0.068*
C7 0.6253 (7) 0.3615 (4) 0.4064 (4) 0.0498 (15)
C8 0.5286 (8) 0.3806 (5) 0.3360 (4) 0.0551 (16)
H8 0.493158 0.436597 0.308917 0.066*
C9 0.4851 (9) 0.3178 (5) 0.3062 (4) 0.0594 (17)
H9 0.418808 0.331695 0.259895 0.071*
C10 0.6693 (7) 0.4292 (4) 0.4397 (4) 0.0480 (14)
C11 0.6820 (8) 0.4174 (4) 0.5237 (4) 0.0522 (15)
H11 0.660567 0.366528 0.559460 0.063*
C12 0.7257 (7) 0.4797 (5) 0.5540 (4) 0.0518 (16)
H12 0.733912 0.469536 0.610079 0.062*
C13 0.7584 (7) 0.5582 (4) 0.5035 (3) 0.0472 (14)
C14 0.7423 (7) 0.5696 (4) 0.4188 (3) 0.0439 (13)
C15 0.6983 (7) 0.5065 (4) 0.3890 (4) 0.0481 (15)
H15 0.687718 0.516343 0.333076 0.058*
C16 0.8057 (7) 0.6226 (5) 0.5401 (4) 0.0505 (15)
C17 0.9106 (8) 0.5978 (5) 0.6076 (4) 0.0547 (16)
H17 0.950961 0.541217 0.628436 0.066*
C18 0.9551 (8) 0.6553 (5) 0.6438 (4) 0.0622 (18)
H18 1.024822 0.637075 0.689065 0.075*
C19 0.8977 (8) 0.7409 (5) 0.6142 (4) 0.0567 (17)
C20 0.7945 (9) 0.7668 (5) 0.5461 (4) 0.0626 (18)
H20 0.757118 0.823646 0.524369 0.075*
C21 0.7473 (8) 0.7083 (5) 0.5109 (4) 0.0558 (16)
H21 0.675024 0.726195 0.466658 0.067*
C22 0.9449 (9) 0.8063 (6) 0.6495 (5) 0.069 (2)
C23 1.0742 (13) 0.8365 (7) 0.7557 (6) 0.104 (3)
H23A 0.979841 0.871895 0.766621 0.124*
H23B 1.143509 0.872006 0.718629 0.124*
C24 1.1654 (16) 0.7901 (9) 0.8332 (6) 0.132 (5)
H24A 1.246074 0.747859 0.823277 0.197*
H24B 1.090974 0.763743 0.872981 0.197*
H24C 1.217704 0.829053 0.853048 0.197*
C25 0.6745 (7) 0.6908 (4) 0.3011 (3) 0.0437 (14)
C26 0.7263 (7) 0.7703 (4) 0.2448 (3) 0.0440 (13)
H26A 0.674273 0.819327 0.259288 0.053*
H26B 0.843273 0.769610 0.248199 0.053*
C27 0.7849 (7) 0.7093 (5) 0.1357 (4) 0.0520 (16)
H27A 0.795986 0.656646 0.178831 0.062*
H27B 0.891904 0.727687 0.125225 0.062*
C28 0.7183 (8) 0.6957 (5) 0.0602 (4) 0.0580 (17)
C29 0.8218 (10) 0.6797 (7) −0.0004 (5) 0.088 (3)
H29 0.933559 0.679370 0.004580 0.106*
C30 0.7566 (13) 0.6644 (8) −0.0671 (6) 0.107 (3)
H30 0.823105 0.655293 −0.108758 0.128*
C31 0.5929 (12) 0.6628 (8) −0.0715 (5) 0.100 (4)
H31 0.546229 0.650449 −0.115093 0.120*
C32 0.4981 (10) 0.6796 (7) −0.0103 (5) 0.081 (3)
H32 0.386244 0.679375 −0.014335 0.097*
C33 0.6911 (7) 0.8591 (4) 0.1062 (4) 0.0514 (15)
H33A 0.796161 0.875177 0.115632 0.062*
H33B 0.686461 0.857182 0.050271 0.062*
C34 0.5607 (7) 0.9238 (4) 0.1184 (3) 0.0463 (14)
C35 0.5871 (9) 1.0080 (5) 0.1009 (4) 0.0558 (17)
H35 0.689015 1.024109 0.084870 0.067*
C36 0.4618 (10) 1.0663 (5) 0.1076 (4) 0.0653 (19)
H36 0.477367 1.122833 0.095558 0.078*
C37 0.3129 (10) 1.0418 (5) 0.1320 (5) 0.0662 (19)
H37 0.225704 1.081154 0.135927 0.079*
C38 0.2956 (9) 0.9572 (5) 0.1506 (4) 0.0598 (17)
H38 0.195178 0.940425 0.168592 0.072*
C39 0.9482 (14) 0.9365 (7) 0.3226 (8) 0.101 (3)
C40 1.0334 (17) 0.9256 (8) 0.3992 (8) 0.131 (5)
H40A 1.104613 0.968348 0.392570 0.197*
H40B 1.096085 0.871004 0.415389 0.197*
H40C 0.955663 0.930318 0.440320 0.197*
N1 0.7753 (5) 0.6470 (3) 0.3627 (3) 0.0439 (11)
H1 0.864473 0.666403 0.368812 0.053*
N2 0.6760 (5) 0.7733 (3) 0.1617 (3) 0.0435 (11)
N3 0.5569 (6) 0.6963 (4) 0.0547 (3) 0.0557 (14)
N4 0.4159 (6) 0.8974 (4) 0.1441 (3) 0.0481 (12)
N5 0.2837 (10) 0.5768 (5) 0.1527 (5) 0.084 (2)
N6 0.1388 (6) 0.8468 (4) 0.0433 (3) 0.0574 (15)
N7 0.1582 (6) 0.7390 (4) 0.3092 (3) 0.0498 (13)
N8 0.8829 (15) 0.9447 (8) 0.2638 (9) 0.148 (5)
O1 0.4032 (9) 0.1835 (4) 0.2501 (4) 0.0921 (19)
O2 0.5247 (7) 0.0905 (4) 0.3599 (3) 0.0766 (15)
O3 0.9154 (9) 0.8809 (5) 0.6172 (4) 0.101 (2)
O4 1.0242 (7) 0.7742 (4) 0.7203 (4) 0.0829 (17)
O5 0.5413 (5) 0.6699 (3) 0.2890 (2) 0.0526 (11)
O6 0.2455 (13) 0.5105 (5) 0.1497 (6) 0.153 (4)
O7 0.2114 (6) 0.6474 (4) 0.1122 (3) 0.0651 (13)
O8 0.4004 (7) 0.5799 (4) 0.1999 (3) 0.0747 (15)
O9 0.1059 (5) 0.8216 (3) 0.1191 (3) 0.0539 (11)
O10 0.0422 (7) 0.8912 (5) −0.0072 (3) 0.101 (2)
O11 0.2802 (5) 0.8219 (3) 0.0246 (3) 0.0596 (12)
O12 0.1569 (5) 0.6855 (3) 0.2694 (3) 0.0571 (11)
O13 0.0668 (5) 0.7394 (3) 0.3652 (3) 0.0610 (13)
O14 0.2603 (5) 0.7913 (3) 0.2872 (3) 0.0566 (11)
Sm1 0.37147 (3) 0.73754 (2) 0.16732 (2) 0.04119 (11)

1 Source of materials

All chemicals were purchased and used as received without further purification. Diethyl 2 -(2-(bis(pyridin-2-ylmethyl)amino)acetamido)-[1,1 :4 , 1 -terphenyl]-4,4 -dicarboxylate (L) was prepared according to previous literature reports [4, 5]. A solution of L (6.3 mg, 0.01 mmol) in acetonitrile (5 mL) was added to a stirred solution of Sm(NO3)3·6H2O (4.5 mg, 0.01 mmol) in acetonitrile (5 mL) at room temperature for 1 h. After filtration, slow diffusion of diethyl ether into the filtrate over 72 h afforded block crystals.

2 Experimental details

All C-bound hydrogen atoms were refined isotropically on calculated positions using a riding model with their U iso values constrained to 1.5 times the U eq of their pivot atoms for terminal sp3 carbon atoms and 1.2 times for all other carbon atoms. One methanol molecule has been removed by solvent mask because it was too unordered: A solvent mask was calculated and 31 electrons were found in a volume of 190 Å3 in 1 void per unit cell.

3 Comment

A tripodal ligand constructed by pyridine and amide could sensitize lanthanide cations which have fascinating optical properties such as long-lived, line-shaped, and position-defined luminescence and the lanthanide complexes have been studied in light-conversion molecular devices and organic light-emitting devices [6], [7], [8], [9]. Some of them have a strong light absorption yield, the multidentate chelate tripodal ligands could coordinated with a lanthanide cation by a helical wrapping configuration of the ligand to build a well-protected coordination environment. In other words, the coordination structures could influence the energy transfer to regulate the luminescence behavior of the lanthanide complexes.

The crystal structure of the complex is shown in the figure. In the asymmetric unit the tripodal ligand takes a fan-like configuration to coordinated to the Sm(III) ion with three bidentate N O 3 anions and a free acetonitrile and a methanol molecule being present in the structure. One apical N, two pyridine N, one amide O, and six nitrate O atoms participate in the coordination of the Sm(III) center to form a 10-coordinating environment. The bond lengths of coordination bonds formed by Sm3+ and tripod are as follows: the Sm1–O5 bond length is 2.442 (4) Å, the Sm1–N2 bond length is 2.654 (4) Å, the Sm1–N3 bond length is 2.638 (5) Å, the Sm1–N4 bond length is 2.649 (5) Å, similar to that reported in Ref. [10]. The bond lengths formed by Sm3+ and six O atoms from three double-toothed N O 3 are respectively: the Sm1–O7 bond length is 2.497(5) Å, the Sm1–O8 bond length is 2.509(6) Å, the Sm1–O9 bond length is 2.477(4) Å, the Sm1–O11 bond length is 2.526(4) Å, the Sm1–O12 bond length is 2.528(4) Å, the Sm1–O14 bond length is 2.581(5) Å, similar to that reported in Ref. [11].


Corresponding author: Hai-Ping Wang, School of Biotechnology and Health Sciences, Wuyi Universty, Guangdong 529020, P.R. China, E-mail:

Acknowledgements

We gratefully acknowledge support by the NSFC of China (21703291) and the NSF of Guangdong Province (2017A030310258).

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

  2. Research funding: NSFC of China (21703291) and the NSF of Guangdong Province (2017A030310258).

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

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Received: 2023-04-04
Accepted: 2023-06-08
Published Online: 2023-07-05
Published in Print: 2023-10-26

© 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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  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
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