Home The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
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The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO

  • Yi-Ding Geng ORCID logo , De-Qi Kong , Ya-Lu Zhang EMAIL logo , Yi-Xiu Zhang and Yi-Xia Gong ORCID logo EMAIL logo
Published/Copyright: April 24, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 4

Abstract

C16H16ClNO, monoclinic, P21/n (no. 14), a = 9.2566 Å, b = 9.2270(7) Å, c = 17.2231(14) Å, β = 103.745(8)°, V = 1428.9(2) Å3, Z = 4, R gt (F) = 0.0655, wR ref (F 2) = 0.2113, T = 293 K.

CCDC no.: 2312788

The crystal structure is shown in the figure above. Tables 1 and 2 contain details of the measurement method and a list of atoms including atomic coordinates and displacement parameters (Table 3).

Table 1:

Data collection and handling.

Crystal: Colourless needle
Size: 0.20 × 0.19 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.26 mm−1
Diffractometer, scan mode: New Gemini, ω
θ max, completeness: 26.1°, >99 %
N(hkl)measured, N(hkl)unique, R int: 5452, 2747, 0.056
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2016
N(param)refined: 174
Programs: Shelx 1 , 2 , Olex2 3
Table 2:

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

Atom x y z U iso */U eq
Cl4 1.29708 (10) 0.84145 (12) 0.49615 (6) 0.0744 (4)
O2 0.9871 (3) 0.8763 (3) 0.41374 (13) 0.0681 (7)
N4 0.8798 (3) 0.7564 (2) 0.49972 (13) 0.0464 (5)
C6 1.1470 (3) 0.8030 (3) 0.53936 (16) 0.0506 (6)
H6A 1.1579 0.7058 0.5614 0.061*
H6B 1.1481 0.8703 0.5828 0.061*
C12 0.9055 (3) 0.7800 (3) 0.64340 (16) 0.0481 (6)
H12 0.9127 0.8800 0.6387 0.058*
C15 0.6784 (3) 0.6403 (3) 0.39544 (15) 0.0462 (6)
C17 0.8885 (3) 0.6922 (3) 0.57668 (15) 0.0431 (6)
C19 0.8737 (3) 0.5441 (3) 0.58417 (16) 0.0500 (6)
H19 0.8614 0.4848 0.5394 0.060*
C23 0.9117 (3) 0.7176 (3) 0.71729 (17) 0.0531 (7)
H23 0.9259 0.7766 0.7622 0.064*
C30 0.5576 (3) 0.5591 (4) 0.40520 (16) 0.0545 (7)
H30 0.5099 0.5838 0.4452 0.065*
C32 0.8973 (3) 0.5702 (4) 0.72574 (16) 0.0512 (7)
C34 0.9989 (3) 0.8150 (3) 0.47790 (16) 0.0498 (6)
C35 0.7483 (3) 0.6011 (4) 0.33546 (18) 0.0554 (7)
H35 0.8294 0.6542 0.3281 0.066*
C40 0.8771 (3) 0.4840 (3) 0.65829 (17) 0.0530 (7)
H40 0.8657 0.3845 0.6628 0.064*
C41 0.7304 (3) 0.7707 (3) 0.44685 (18) 0.0545 (7)
H41A 0.7296 0.8540 0.4124 0.065*
H41B 0.6602 0.7896 0.4794 0.065*
C55 0.6977 (4) 0.4840 (4) 0.28679 (19) 0.0672 (9)
H55 0.7454 0.4578 0.2471 0.081*
C59 0.5769 (4) 0.4057 (4) 0.2968 (2) 0.0675 (9)
H59 0.5422 0.3277 0.2633 0.081*
C62 0.9030 (5) 0.5037 (5) 0.8068 (2) 0.0816 (11)
H62A 1.0029 0.5081 0.8390 0.122*
H62B 0.8714 0.4044 0.8001 0.122*
H62C 0.8381 0.5564 0.8326 0.122*
C67 0.5075 (4) 0.4424 (4) 0.3562 (2) 0.0653 (8)
H67 0.4268 0.3885 0.3633 0.078*
Table 3:

Fractional atomic coordinates and displacement parameters (Å2).

Atom x y z U 11 U 22 U 33 U 23 U 13 U 12
Cl4 12970.8 (10) 8414.5 (12) 4961.5 (6) 0.0697 (6) 0.0874 (7) 0.0750 (6) −0.0001 (4) 0.0346 (5) −0.0070 (4)
O2 9871 (3) 8763 (3) 4137.4 (13) 0.0912 (17) 0.0686 (14) 0.0417 (11) 0.0135 (10) 0.0104 (11) −0.0056 (12)
N4 8798 (3) 7564 (2) 4997.2 (13) 0.0521 (12) 0.0511 (13) 0.0322 (11) −0.0008 (8) 0.0026 (9) 0.0015 (9)
C6 11470 (3) 8030 (3) 5393.6 (16) 0.0620 (16) 0.0516 (15) 0.0391 (13) −0.0030 (11) 0.0137 (12) −0.0019 (11)
C12 9055 (3) 7800 (3) 6434.0 (16) 0.0505 (14) 0.0528 (14) 0.0405 (14) −0.0118 (11) 0.0099 (11) −0.0062 (11)
C15 6784 (3) 6403 (3) 3954.4 (15) 0.0404 (12) 0.0621 (15) 0.0319 (12) 0.0046 (10) 0.0005 (9) 0.0099 (10)
C17 8885 (3) 6922 (3) 5766.8 (15) 0.0426 (12) 0.0531 (14) 0.0325 (12) −0.0062 (10) 0.0067 (9) 0.0024 (10)
C19 8737 (3) 5441 (3) 5841.7 (16) 0.0563 (14) 0.0529 (15) 0.0382 (13) −0.0081 (11) 0.0060 (11) 0.0036 (11)
C23 9117 (3) 7176 (3) 7172.9 (17) 0.0561 (15) 0.0660 (17) 0.0377 (13) −0.0100 (12) 0.0123 (11) −0.0085 (13)
C30 5576 (3) 5591 (4) 4052.0 (16) 0.0525 (15) 0.0726 (18) 0.0405 (14) 0.0116 (12) 0.0151 (11) 0.0060 (13)
C32 8973 (3) 5702 (4) 7257.4 (16) 0.0387 (12) 0.0764 (18) 0.0381 (13) 0.0022 (12) 0.0085 (10) −0.0063 (11)
C34 9989 (3) 8150 (3) 4779.0 (16) 0.0676 (17) 0.0430 (13) 0.0376 (13) −0.0016 (10) 0.0100 (12) 0.0018 (11)
C35 7483 (3) 6011 (4) 3354.6 (18) 0.0436 (13) 0.0766 (19) 0.0468 (15) −0.0052 (14) 0.0124 (11) −0.0034 (12)
C40 8771 (3) 4840 (3) 6582.9 (17) 0.0532 (14) 0.0553 (15) 0.0494 (15) 0.0026 (12) 0.0100 (12) −0.0013 (12)
C41 7304 (3) 7707 (3) 4468.5 (18) 0.0545 (16) 0.0577 (15) 0.0460 (15) 0.0004 (12) 0.0013 (12) 0.0151 (12)
C55 6977 (4) 4840 (4) 2867.9 (19) 0.0620 (17) 0.092 (2) 0.0504 (17) −0.0196 (16) 0.0182 (14) −0.0033 (16)
C59 5769 (4) 4057 (4) 2968 (2) 0.0608 (18) 0.070 (2) 0.064 (2) −0.0146 (16) −0.0001 (15) −0.0042 (14)
C62 9030 (5) 5037 (5) 8068 (2) 0.089 (3) 0.105 (3) 0.0526 (19) 0.0156 (18) 0.0197 (17) −0.014 (2)

1 Source of material

Benzaldehyde (1 g, 9.42 mmol) was added to the stirred anhydrous magnesium sulfate (15 g), then dichloromethane (100 ml), finally 4-methylaniline (1.01 g, 9.42 mmol), and the reaction mixture was stirred for 6 h at room temperature. The reaction mixture was filtered and the filtrate was concentrated to obtain the crude product (E)-1-phenyl-N-(p-tolyl)methanimine, light yellow clear oil (1.77 g, yield 96.2 %). To (E)-1-phenyl-N-(p-tolyl)methanimine (1 g, 5.12 mmol) in a solution in anhydrous methanol (150 ml), we slowly added sodium borohydride (0.77 g, 20.48 mmol) for 0.5 h at low temperature, then moved to room temperature for 2 h. The solvent was steamed and dried, and a small amount of dichloromethane and dilute hydrochloric acid were added to regulate pH = 1–2. The product was washed three times with dichloromethane (30 ml), the combined organic phase, dried with anhydrous magnesium sulfate, and steamed to obtain light yellow solid (0.96 g, yield 95.02 %). 4 We added triethylamine (1.06 ml, 7.60 mmol) to a solution of N-benzyl-4-methylaniline (1 g, 5.07 mmol) in dichloromethane (100 ml), and then added chloroacetyl chloride (1.03 g, 9.12 mmol) dropwise after a 0.5 h ice salt bath. After addition, we stabilize at low temperature for 1 h. Transferred to room temperature and stirred for 9 h. Then we extracted the organic layer from a saturated salt aqueous solution and merged the organic layers. We dried with anhydrous magnesium sulfate, filtered, and evaporated the filtrate to obtain a light yellow solid (1.24 g, yield 89.36 %). The compounds were dissolved in dichloromethane/methanol. The solvent was then slowly volatilized in the air at low temperatures. A few days later, the crystals of the compound were obtained. 1 H-NMR (600 MHz, DMSO-d6) d 7.31–7.27 (m, 2H), 7.26–7.21 (m, 1H), 7.21–7.17 (m, 4H), 7.12–7.08 (m, 2H), 4.86 (s, 2H), 4.06 (s, 2H), 2.29 (s, 3H). 13 C-NMR (151 MHz, DMSO-d6) d 165.66, 138.14, 136.93, 130.07, 129.22, 128.33, 127.90 (d, J = 21.8 Hz), 52.66, 42.35, 20.57. MS(ESI):m/z = 274.0900 [M+H]+; FTIR (KBr, cm−1), 3003.12 (C–H methyl), 2933.69 (C–H methylene), 1668.40 (C=O ketone), 1508.31 (C=C benzene double bonds), 1398.37 (C–N amide bond), 752.23 (C–Cl carbon chlorine single bond).

2 Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

The amide bond is undoubtedly one of the most important structural motifs in nature. 5 , 6 Amides are not only restricted to biological systems but also undeniably present in an enormous array of molecules, along with major marketed drugs. In addition, the US FDA approved drugs like imatinib (Bcr-Abl tyrosine-kinase inhibitor), nilotinib (tyrosine-kinase inhibitor), ponatinib (multi-targeted tyrosine-kinase inhibitor), dasatinib (tyrosine-kinase inhibitor), afatinib (tyrosine kinase inhibitor), methotrexate (dihydrofolate reductase inhibitor) and carfilzomib (selective proteasome inhibitor) which are used for the treatment of different types of cancers also carry amide bond as an indispensable structural motif. 7 And the acylation of amine is one of the most widely practiced reactions in the pharmaceutical industry. 8 The crystal molecular packing of the title compound was formed by hydrogen bonds and van der Waals interactions. The hydrogen bond in the molecular structure of the target compound includes one intramolecular C41–H41A⋯O2 (2.750 Å) hydrogen bond. The above mentioned interactions play an important role in the stability of the crystal structure. Geometric parameters are all in the expected ranges. 9

Corresponding authors: Ya-Lu Zhang, Department of Pharmacy, Yanzhou District People’s Hospital of Jining City, Jining, 272100, P.R. China, E-mail: ; and Yi-Xia Gong, College of Pharmacy, Jiamusi University, Jiamusi, 154007, P.R. China, E-mail:

  1. Author contribution: 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 the Excellent youth project of Heilongjiang Natural Science Foundation (YQ2021H027), and the project of Cultivating Young Innovative Talents in Heilongjiang Province (UNPYSCT-2020056), and National Fund Cultivation Program of Jiamusi University (JMSUGPZR2022-007).

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

References

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Received: 2024-03-08
Accepted: 2024-04-11
Published Online: 2024-04-24
Published in Print: 2024-08-27

© 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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  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
https://doi.org/10.1515/ncrs-2024-0117
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]−} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 −)
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
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