Startseite Crystal structure of 2-amino-4-(4-bromo-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H11BrN2O3
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Crystal structure of 2-amino-4-(4-bromo-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H11BrN2O3

  • Xue-Jun Yu EMAIL logo , Lin-Ping Zhao , Long-Ji Ma und Hua-Fen Gong
Veröffentlicht/Copyright: 1. November 2016

Abstract

C16H11BrN2O3, monoclinic, C2/c, a = 21.504(3) Å, b = 8.2788(10) Å, c = 18.170(3) Å, β = 110.511(5)°, V = 3029.8(7) Å3, Z = 8, Rgt(F) = 0.0429, wRref(F2) = 0.1251, T = 296 K.

CCDC no.:: 1510293

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless blocks
Size:0.18 × 0.16 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:27.3 cm−1
Diffractometer, scan mode:Bruker XSCANS, ω-scans
2θmax, completeness:50°, >99%
N(hkl)measured, N(hkl)unique, Rint:9161, 2663, 0.023
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2213
N(param)refined:199
Programs:SHELX [7], Bruker programs [8]
Table 2:

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

AtomxyzUiso*/Ueq
C1−0.15561(14)0.7447(4)−0.23949(17)0.0474(7)
C2−0.16301(14)0.8920(3)−0.20193(17)0.0432(6)
C3−0.15003(15)1.0332(3)−0.23085(18)0.0472(7)
C4−0.12421(19)1.0379(4)−0.2927(2)0.0598(9)
H4A−0.11561.1363−0.31190.072*
C5−0.11255(18)0.9000(4)−0.3229(2)0.0593(8)
C6−0.0816(2)0.8764(6)−0.3836(3)0.0862(13)
H6A−0.07100.9796−0.40020.129*
H6B−0.11210.8204−0.42780.129*
H6C−0.04170.8139−0.36190.129*
C7−0.18528(14)1.1865(3)−0.14360(17)0.0462(7)
C8−0.19815(14)1.0511(3)−0.10985(17)0.0424(6)
C9−0.18439(13)0.8813(3)−0.13198(17)0.0419(6)
H9A−0.22560.8188−0.14660.050*
C10−0.22607(16)1.0648(3)−0.0507(2)0.0507(7)
C11−0.13245(13)0.7989(3)−0.06265(16)0.0406(6)
C12−0.06519(14)0.8254(4)−0.04449(18)0.0518(7)
H12A−0.05120.8939−0.07610.062*
C13−0.01846(15)0.7528(4)0.01928(19)0.0589(8)
H13A0.02660.77090.03010.071*
C14−0.03920(15)0.6534(4)0.06666(18)0.0534(7)
C15−0.10578(17)0.6263(4)0.0509(2)0.0589(8)
H15A−0.11960.56000.08360.071*
C16−0.15181(15)0.6982(4)−0.01385(19)0.0518(7)
H16A−0.19680.6786−0.02490.062*
O1−0.15946(12)1.1804(2)−0.20255(13)0.0556(5)
O2−0.12832(12)0.7553(3)−0.29775(13)0.0585(6)
O3−0.17084(11)0.6110(3)−0.22451(13)0.0578(6)
N1−0.19546(15)1.3389(3)−0.12754(18)0.0633(8)
H1A−0.21211.3599−0.09190.076*
H1B−0.18541.4165−0.15280.076*
N2−0.24789(19)1.0700(3)−0.0018(2)0.0748(10)
Br10.02508(2)0.55281(5)0.15404(2)0.0848(2)

Source of material

The title compound was synthesized according to a reported procedure [6]. A mixture of 4-hydroxy-6-methylpyran-2-one (10 mmol), 4-bromobenzaldehyde (10 mmol), malononitrile (10 mmol) and 4-(dimethylamino)pyridine (DMAP) (1 mmol) in ethanol (100 mL) was refluxed for 2–3 h and then cooled to room temperature. After filtering the precipitates, they were sequentially washed with ice-cooled water and ethanol and then dried under vacuum.

Experimental details

The H atoms bonded to C and N were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and 0.86 Å and with Uiso(H) = 1.2Ueq(C,N).

Discussion

The synthesis of pyrans and their derivatives has attracted considerable attention from organic and medicinal chemists for many years as a large number of natural and synthetic products contain this heterocyclic nucleus [1, 2]. Pyrans possess diverse pharmacological and biological activities such as antitumor, analgesic and ulcerogenic, anti-inflammatory, anticoagulant, phototriggering, and fungicidal properties, and can act as anticoagulants in the production of pesticides [3, 4]. In particular, the anticancer activity of pyran compounds has received considerable attention because of their cytotoxic activity against numerous types of cancers, including malignant melanoma, leukemia, renal cell carcinoma, prostate and breast cancer cell progression [5].

In the crystal structure of the title compound, the 4H-pyran ring is nearly planar and the adjacent pyran-2-on-3,4-diyl ring also adopts an almost planar conformation. The plane of the heterocyclic moiety is almost perpendicular to the mean plane of the bromophenyl substituent (cf. the figure).

References

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2 Li, J.; Meng, J.; Qu, D.; Zhang, Z.-d.; Li, F.; Yang, X.-H.; Li, J.-T.; Li, M.-K.: New biscoumarin and dihydropyran derivatives as antimicrobials. Res. Chem. Intermed. 41 (2015) 8257–8267.10.1007/s11164-014-1889-xSuche in Google Scholar

3 Li, J.; Xue, X. Y.; Li, X.; Hou, Z.; Yang, X. H.; Qu, D.; Zhou, Y.; Zhang; Z. D; Luo, X. X.; Li, J. T.; Li, M. K.: Synthesis of biscoumarin and dihydropyran derivatives and evaluation of their antibacterial activity. Molecules. 20 (2015) 17469–17482.10.3390/molecules200917469Suche in Google Scholar PubMed PubMed Central

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Received: 2016-6-13
Accepted: 2016-10-17
Published Online: 2016-11-1
Published in Print: 2017-1-1

©2016 Xue-Jun Yu et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  1. Cover and Frontmatter
  2. Editorial
  3. Twenty years of crystal structure publication and the road ahead
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  17. Crystal structure of 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea, C17H21ClN2S
  18. Crystal structure of 3-(adamantan-1-yl)-1-(4-bromophenyl)urea, C17H21BrN2O
  19. Crystal structure of (Z)-Ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene) acetate, C14H14N2O2S
  20. Crystal structure of methyl 2b-ethyl-1a,2a,2b,2b1,3,5,10,11-octahydro-1H-oxireno[2′,3′:6,7]indolizino[8,1-cd]carbazole-4-carboxylate, C21H24N2O3
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  22. Crystal structure of 1,2,3-trimethyl-2,3-dihydro-1H-perimidine, C14H16N2
  23. Crystal structure of bis(2,6-dihydroxymethyl)pyridine-κ3N,O,O′)-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-bis(6-chloropyridin-2-olato-κO)-bis(nitrato-κ2O,O′)digadolinium(III), C34H30Cl4Gd2N8O14
  24. Crystal structure of 8-isopropyl-8-aza-bicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate, C19H27NO3
  25. Crystal structure of 1-methyl-3-[((naphthalen-2-ylsulfonyl)oxy)imino]indolin-2-one, C19H14N2O4S
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  28. Crystal structure of 2-[(2-oxo-thiazolidine-3-carbonyl)sulfamoyl]-methy-benzoic acid methyl ester, C13H14N2O6S2
  29. Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C13H14N2O3S
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  33. Crystal structure of bis(μ-nitrato-κ2O:O)-bis[1,2-bis(diphenylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]disilver(I) dicloromethane monosolvate, C54H64B20Cl4O6P4Ag2
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