Home The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
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The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3

  • Sadeekah O. Saber ORCID logo , Yaseen A. Al-Soud , Raed A. Al-Qawasmeh and Monther A. Khanfar ORCID logo EMAIL logo
Published/Copyright: February 3, 2025
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 2

Abstract

C12H9Br2N3O3, monoclinic, P21/c (no. 14), a = 9.0255(5) Å, b = 14.9112(5) Å, c = 10.9438(5) Å, β = 109.223(5)°, V = 1390.71(12) Å3, Z = 4, Rgt(F) = 0.0482, wRref(F2) = 0.0948, T = 293(2) K.

CCDC no.: 2416949

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: Clear colourless block
Size: 0.22 × 0.16 × 0.01 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 5.84 mm−1
Diffractometer, scan mode: Xcalibur, Eos, φ and ω scans
θmax, completeness: 29.4°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 11361, 3325, 0.034
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2,459
N(param)refined: 187
Programs: Bruker, 1 Olex2, 2 SHELX 3
Table 2:

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

x y z Uiso*/Ueq
Br1 0.14800 (6) 0.66340 (3) 0.25408 (4) 0.04043 (16)
Br2 0.05169 (6) 0.37422 (4) 0.10680 (5) 0.04954 (18)
O3 0.4769 (4) 0.4077 (2) 0.3042 (3) 0.0491 (9)
N1 0.2100 (4) 0.4797 (2) 0.3232 (3) 0.0277 (8)
O1 0.1415 (4) 0.5944 (2) 0.6730 (3) 0.0472 (9)
O2 0.1287 (5) 0.6970 (2) 0.5302 (3) 0.0531 (10)
N3 0.2018 (4) 0.4656 (2) 0.5234 (3) 0.0329 (8)
N4 0.1470 (4) 0.6191 (3) 0.5682 (3) 0.0337 (8)
C4 0.1755 (5) 0.5523 (3) 0.4832 (4) 0.0265 (9)
C6 0.2192 (5) 0.4578 (3) 0.1975 (4) 0.0284 (9)
C5 0.1780 (5) 0.5636 (2) 0.3613 (4) 0.0263 (9)
C8 0.4056 (5) 0.4003 (3) 0.0773 (4) 0.0312 (9)
C2 0.2229 (5) 0.4225 (3) 0.4267 (4) 0.0314 (9)
C7 0.3806 (5) 0.4193 (3) 0.2028 (4) 0.0303 (9)
C9 0.5384 (6) 0.3500 (3) 0.0823 (5) 0.0401 (11)
H9 0.6057 0.3294 0.1613 0.048*
C13 0.3082 (6) 0.4323 (3) −0.0414 (4) 0.0367 (10)
H13 0.2207 0.4667 −0.0455 0.044*
C12 0.3414 (7) 0.4129 (3) −0.1539 (5) 0.0477 (13)
H12 0.2764 0.4342 −0.2333 0.057*
C10 0.5691 (6) 0.3313 (3) −0.0301 (5) 0.0490 (13)
H10 0.6569 0.2975 −0.0269 0.059*
C11 0.4710 (7) 0.3620 (3) −0.1469 (5) 0.0511 (14)
H11 0.4925 0.3484 −0.2223 0.061*
C14 0.2489 (7) 0.3238 (3) 0.4275 (5) 0.0509 (14)
H14A 0.1708 0.2971 0.3547 0.076*
H14B 0.2415 0.2986 0.5061 0.076*
H14C 0.3513 0.3120 0.4224 0.076*
H6 0.201 (5) 0.508 (3) 0.152 (4) 0.024 (11)*

1 Source of materials

The title compound was synthesized via double bromination of the precursor 2-(2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone. The reaction was performed using liquid bromine in DMF, in the presence of potassium carbonate as a base. The new compound 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone crystallized as off-white crystal in 84 % yield from dichloromethane-diethyl ether system. Melting Point: 176–178 °C. HRMS–ESI m/z: 401.89414 (M +H)+. 1H NMR (500 MHz, DMSO‑d6, 298 K): δ 2.51 (s, 3H, H–C14); 7.51 (pseudo t, 2H, H–C10, H–C12); 7.63 (t, 1H, J = 7.4 Hz, H–C11); 7.82 (d, 2H, J = 7.7 Hz, H–C9, H–C13); 8.39 (s, 1H, H–C6). 13C NMR (125 MHz, DMSO‑d6, 298 K); δ 15.2 (C14); 59.7 (C6); 107.4 (C4); 129.2 (C9, C13); 129.4 (C10, C12); 132.9 (C11); 134.7 (C8); 144.9 (C2); 146.9 (C4); 187.3 (C7).

2 Experimental details

The chemicals were purchased from Aldrich (Germany), Fluka (Switzerland), and Scharlau, they were used without further purification, unless otherwise stated.

The NMR spectra were recorded on a Bruker Avance III-(500 MHz) spectrometer with tetramethylsilane (TMS) as an internal standard. 1H NMR (500 MHz), 13C NMR (125 MHz) were recorded in dimethylsulfoxide (DMSO‑d6). The following abbreviations are used to describe peak patterns: s = singlet, t = triplet, d = doublet. High-resolution mass spectra (HRMS) were measured (in positive/or negative ion mode) using the electro spray ion trap (ESI po slow mass) technique by collision-induced dissociation on a Bruker APEX–IV (7 Tesla) instrument. Melting points were determined on a Stuart (SMP-10) melting point apparatus. Single crystal of C12H9Br2N3O3 was obtained through crystallization of the pure compound from CH2Cl2/Et2O. Using Olex2, 2 the structure was solved with the ShelXT 3 structure solution program and refined with the ShelXL 4 refinement package. All H atoms bonded to C atoms were refined as riding, with CH distances of 0.93 Å (for aromatic ring).

3 Discussion

Imidazole forms the main structure of some well-known components of human organisms, that is, histidine, Vit–B12, a component of DNA base structure and purines, histamine and biotin. It is also present in the structure of many natural or synthetic drug molecules. 5 For example, lepidiline A and B exhibit significant cytotoxicity against various types of human cancer cell lines at micromolar concentrations. 6 Dacarbazine, 7 zoledronic acid 8 and azathioprine 9 are also potent anticancer agents bearing an imidazole ring. In consideration of the high therapeutic properties of the nitroimidazole-related drugs and in continuation of our research on the synthesis and biological evaluation of imidazole analogs, 10 , 11 , 12 , 13 , 14 , 15 , 16 we here present the important nucleus as imidazolyl containing title structure. Herein, the 2-bromo-1-phenylethane-1-one was coupled with imidazole ring to produce the target compound. The measurement shows that the title crystal structure consists of the monomeric molecules. In the title molecules all bond lengths are in normal ranges. 17 The average plane of imidazole ring is twisted (57.9(4)°) to the average plane of the ethanone group (C6 C7 C8). The shortest hydrogen intramolecular interactions are CH⋯O (C14H14A⋯O3, = 2.442(4) Å) and CH⋯Br interactions (C6H6⋯Br1 = 2.69(4) Å and C14H14C⋯Br2 = 2.8137(6) Å). The crystal is stabilized via CH…O (H10…O2 (1 − x, −1/2 + y, 1/2 − z) = 2.457(4) Å) and CH⋯N (H12⋯N3 (+x, +y, 1 + z) = 2.565(3) Å) interactions.

Corresponding author: Monther A. Khanfar, Department of Chemistry, Pure and Applied Chemistry Group, College of Sciences, University of Sharjah, Sharjah 27272, UAE; and Department of Chemistry, The University of Jordan, Amman 11942, Jordan, E-mail:

Funding source: The office of the vice chancellor for research and graduate studies .

Award Identifier / Grant number: funded Project 23021440137

  1. Research funding: RAA thanks the office of the vice chancellor for research and graduate studies for funded Project 23021440137.

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Received: 2024-12-29
Accepted: 2025-01-14
Published Online: 2025-02-03
Published in Print: 2025-04-28

© 2025 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-2024-0489
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
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