Crystal structure of N-((3s,5s,7s)-adamantan-1-yl)-2-(3-benzoylphenyl)propanamide, C26H29NO2

Li-Na Gao; Ye Gu; Feng Jin; Duo Hao; Xin-Ru Zhang

doi:10.1515/ncrs-2022-0107

Open Access Published by De Gruyter (O) April 20, 2022

Crystal structure of N-((3s,5s,7s)-adamantan-1-yl)-2-(3-benzoylphenyl)propanamide, C₂₆H₂₉NO₂

Li-Na Gao , Ye Gu , Feng Jin , Duo Hao and Xin-Ru Zhang

From the journal Zeitschrift für Kristallographie - New Crystal Structures

https://doi.org/10.1515/ncrs-2022-0107

Abstract

C₂₆H₂₉NO₂, triclinic, P 1 ‾ (no. 2), a = 10.8490(8) Å, b = 13.2892(9) Å, c = 14.7199(10) Å, α = 89.161(3)°, β = 79.991(2)°, γ = 85.746(2)°, V = 2084.2(3) Å³, Z = 4, R _gt(F) = 0.0641, wR _ref(F ²) = 0.1449, T = 170 K.

CCDC no.: 2158053

The crystal 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:	Needle, colorless
Size:	0.07 × 0.05 × 0.02 mm
Wavelength:	Mo Kα radiation (0.71073 Å)
μ:	0.08 mm⁻¹
Diffractometer, scan mode:	Bruker D8 VENTURE, φ and ω-scans
θ _max, completeness:	26.4°, >99%
N(hkl)_measured, N(hkl)_unique, R _int:	24,187, 8510, 0.087
Criterion for I _obs, N(hkl)_gt:	I _obs > 2 σ(I _obs), 4647
N(param)_refined:	525
Programs:	Bruker programs [1], OLEX2 [2], SHELX [3, 4]

Table 2:

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

	x	y	z	U _iso*/U _eq
O1	0.41944 (17)	0.64618 (13)	0.53751 (13)	0.0367 (5)
O2	0.22477 (17)	0.16961 (13)	0.39002 (13)	0.0359 (5)
O3	0.05772 (17)	0.37384 (13)	0.80212 (13)	0.0387 (5)
O4	−0.18575 (18)	−0.10893 (13)	0.97631 (13)	0.0385 (5)
N1	0.4200 (2)	0.22835 (15)	0.36273 (15)	0.0301 (5)
H1	0.467632	0.270759	0.382933	0.036*
N2	0.1894 (2)	0.28132 (16)	0.88122 (15)	0.0312 (6)
H2A	0.193388	0.229561	0.918833	0.037*
C1	0.3389 (3)	0.8493 (2)	0.49712 (18)	0.0319 (7)
H1A	0.426794	0.835949	0.478366	0.038*
C2	0.2874 (3)	0.9479 (2)	0.50782 (19)	0.0385 (8)
H2	0.339941	1.002332	0.495110	0.046*
C3	0.1601 (3)	0.9672 (2)	0.5369 (2)	0.0401 (8)
H3	0.125495	1.034927	0.545093	0.048*
C4	0.0827 (3)	0.8888 (2)	0.55409 (19)	0.0350 (7)
H4	−0.004942	0.902392	0.574400	0.042*
C5	0.1331 (2)	0.79048 (19)	0.54165 (17)	0.0281 (6)
H5	0.079431	0.736603	0.552172	0.034*
C6	0.2610 (2)	0.76951 (19)	0.51397 (17)	0.0257 (6)
C7	0.3190 (2)	0.66463 (19)	0.51010 (18)	0.0289 (6)
C8	0.2559 (2)	0.58170 (18)	0.47470 (17)	0.0250 (6)
C9	0.2895 (2)	0.48202 (18)	0.49771 (18)	0.0261 (6)
H9	0.349100	0.469448	0.537543	0.031*
C10	0.2378 (2)	0.40133 (19)	0.46369 (18)	0.0263 (6)
C11	0.1530 (2)	0.42127 (19)	0.40351 (18)	0.0314 (7)
H11	0.117687	0.366787	0.378682	0.038*
C12	0.1196 (2)	0.5190 (2)	0.37941 (19)	0.0336 (7)
H12	0.061925	0.531211	0.338058	0.040*
C13	0.1698 (2)	0.5993 (2)	0.41529 (18)	0.0293 (6)
H13	0.145457	0.666534	0.399348	0.035*
C14	0.2712 (2)	0.29479 (18)	0.49404 (18)	0.0279 (6)
H14	0.347783	0.296034	0.523149	0.033*
C15	0.1662 (2)	0.2564 (2)	0.56602 (19)	0.0339 (7)
H15A	0.093189	0.246405	0.537050	0.051*
H15B	0.142510	0.305909	0.615813	0.051*
H15C	0.195351	0.192102	0.591370	0.051*
C16	0.3029 (2)	0.22410 (18)	0.41076 (18)	0.0271 (6)
C17	0.4769 (2)	0.16949 (19)	0.27988 (18)	0.0282 (6)
C18	0.4892 (3)	0.05732 (19)	0.30293 (18)	0.0326 (7)
H18A	0.404854	0.032784	0.323367	0.039*
H18B	0.537426	0.046619	0.353949	0.039*
C19	0.5562 (3)	−0.0018 (2)	0.21806 (19)	0.0375 (7)
H19	0.565010	−0.075047	0.234037	0.045*
C20	0.6860 (3)	0.0359 (2)	0.1851 (2)	0.0454 (8)
H20A	0.728770	−0.002791	0.130154	0.055*
H20B	0.737543	0.025776	0.234258	0.055*
C21	0.6074 (2)	0.2064 (2)	0.24681 (19)	0.0349 (7)
H21A	0.599946	0.279357	0.232332	0.042*
H21B	0.658354	0.196650	0.296337	0.042*
C22	0.6723 (3)	0.1481 (2)	0.1610 (2)	0.0416 (8)
H22	0.757226	0.173031	0.139676	0.050*
C23	0.5942 (3)	0.1628 (2)	0.08409 (19)	0.0413 (8)
H23A	0.585979	0.235116	0.067494	0.050*
H23B	0.636246	0.124722	0.028560	0.050*
C24	0.4646 (3)	0.1250 (2)	0.11747 (19)	0.0360 (7)
H24	0.413216	0.134882	0.067391	0.043*
C25	0.4777 (3)	0.0126 (2)	0.14111 (19)	0.0386 (7)
H25A	0.519246	−0.026106	0.085831	0.046*
H25B	0.393724	−0.012541	0.161747	0.046*
C26	0.3995 (2)	0.1852 (2)	0.20267 (18)	0.0306 (7)
H26A	0.391196	0.257804	0.186998	0.037*
H26B	0.314356	0.162348	0.223474	0.037*
C27	0.3080 (2)	0.32883 (19)	0.84786 (18)	0.0277 (6)
C28	0.4109 (2)	0.26850 (19)	0.88859 (19)	0.0307 (7)
H28A	0.389897	0.269978	0.956776	0.037*
H28B	0.416094	0.197305	0.868501	0.037*
C29	0.5371 (3)	0.3126 (2)	0.85723 (19)	0.0368 (7)
H29	0.603460	0.271903	0.883905	0.044*
C30	0.5700 (3)	0.3104 (2)	0.7523 (2)	0.0462 (8)
H30A	0.575989	0.239906	0.730172	0.055*
H30B	0.652166	0.338671	0.731867	0.055*
C31	0.3420 (3)	0.3271 (2)	0.74241 (18)	0.0364 (7)
H31A	0.347420	0.256791	0.720049	0.044*
H31B	0.275978	0.366341	0.715419	0.044*
C32	0.4679 (3)	0.3727 (2)	0.7121 (2)	0.0431 (8)
H32	0.489450	0.371792	0.643220	0.052*
C33	0.4588 (3)	0.4814 (2)	0.7459 (2)	0.0499 (9)
H33A	0.539701	0.511637	0.725325	0.060*
H33B	0.392977	0.521676	0.719538	0.060*
C34	0.4267 (3)	0.4828 (2)	0.8508 (2)	0.0405 (8)
H34	0.421323	0.554040	0.872932	0.049*
C35	0.5294 (3)	0.4211 (2)	0.8908 (2)	0.0433 (8)
H35A	0.611053	0.450411	0.870841	0.052*
H35B	0.509893	0.422782	0.959019	0.052*
C36	0.3004 (2)	0.43794 (19)	0.8821 (2)	0.0332 (7)
H36A	0.233784	0.478587	0.856992	0.040*
H36B	0.279020	0.439345	0.950269	0.040*
C37	0.0757 (3)	0.30912 (19)	0.85996 (19)	0.0297 (6)
C38	−0.0321 (2)	0.25326 (19)	0.91357 (19)	0.0303 (6)
H38	−0.005128	0.224587	0.970803	0.036*
C39	−0.1457 (3)	0.3283 (2)	0.9421 (2)	0.0451 (8)
H39A	−0.122647	0.381884	0.979680	0.068*
H39B	−0.214350	0.293227	0.978121	0.068*
H39C	−0.172851	0.357987	0.886867	0.068*
C40	−0.0644 (2)	0.16670 (19)	0.85761 (18)	0.0280 (6)
C41	−0.1085 (2)	−0.00924 (19)	0.84789 (18)	0.0279 (6)
C42	−0.0817 (2)	0.07249 (19)	0.89804 (19)	0.0291 (6)
H42	−0.075183	0.063417	0.961208	0.035*
C43	−0.1212 (2)	0.0043 (2)	0.75641 (19)	0.0329 (7)
H43	−0.138066	−0.050983	0.721388	0.039*
C44	−0.1093 (3)	0.0987 (2)	0.71620 (19)	0.0370 (7)
H44	−0.121459	0.108908	0.654260	0.044*
C45	−0.0797 (3)	0.1784 (2)	0.76609 (19)	0.0349 (7)
H45	−0.069633	0.242341	0.737185	0.042*
C46	−0.1286 (2)	−0.1076 (2)	0.89638 (19)	0.0301 (6)
C47	0.0337 (3)	−0.2093 (2)	0.78646 (19)	0.0336 (7)
H47	0.070730	−0.148937	0.764773	0.040*
C48	−0.0761 (2)	−0.20400 (19)	0.85006 (18)	0.0277 (6)
C49	0.0906 (3)	−0.3015 (2)	0.7539 (2)	0.0355 (7)
H49	0.167701	−0.304424	0.711639	0.043*
C50	0.0352 (3)	−0.3893 (2)	0.7829 (2)	0.0365 (7)
H50	0.073884	−0.452640	0.760396	0.044*
C51	−0.0763 (3)	−0.3850 (2)	0.8446 (2)	0.0378 (7)
H51	−0.115107	−0.445340	0.863836	0.045*
C52	−0.1314 (3)	−0.2935 (2)	0.87832 (19)	0.0346 (7)
H52	−0.207761	−0.291091	0.921284	0.041*

Source of materials

The ketoprofen (0.77 g, 3 mmol), oxalyl chloride (2.92 ml, 40 mmol) and one drop DMF were added to the reaction flask. The mixture was refluxed for 1 h and then the solvent was removed under reduced pressure. The residue was dissolved in 15 ml dichloromethane, followed by amantadine (0.37 g, 2.5 mmol) and triethylamine (0.42 ml, 3 mmol) at 0 °C and the reaction solution was stirred at room temperature for 3 h. After completion of the reaction, the solution was extracted three times with 15 ml methylene chloride. The organic phase was dehydrated with sodium sulfate and concentrated at reduced pressure to afford a light yellow solid. the solid was purified by column chromatography to give title compound (0.67 g), Yield 68.3%.

Experimental details

All hydrogen atoms were placed in geometrically calculated positions. The U _iso values of the hydrogen atoms of methyl groups were set to 1.5 U _eq (C methyl) and the U _iso values of all other hydrogen atoms were set to 1.2 U _eq(C).

Discussion

Adamantanamine and its derivatives play an important role in pharmaceuticals as well as medicinal chemistry because they possess a broad spectrum of biological activities [5], [6], [7], [8]. As a result, a great deal of attention has been paid to the investigation on the structure and property of amantadine and its derivatives. The aim of this study was to further optimize the organic synthesis and structural modification of amantadine amino based materials to design a suitable synthesis route to get novel compounds by a 1–2 steps reaction.

There are two crystallographically independent molecules in the asymmetric unit. Both molecules have almost the same geometric parameters. Thus only one of them is discussed in more detail (cf. the figure). The two aryl rings are linked by a keto group. Additionally, the amino-adamantyl moiety is attached to the second ketone group of the title molecules. The bond distances and angles are in their normal ranges according to the previously reported compounds [9], [10], [11].

Corresponding author: Xin-Ru Zhang, The Second Hospital of Jilin University, Changchun 130000, P. R. China, E-mail: xinru@jlu.edu.cn

Funding source: Medical and Health Talents Special Project of Jilin Province

Award Identifier / Grant number: 2019SCZT086

Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: This work was supported by Medical and Health Talents Special Project of Jilin Province (2019SCZT086).
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2022-03-07

Accepted: 2022-04-05

Published Online: 2022-04-20

Published in Print: 2022-08-26

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