organic compounds
3-{[1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranos-1-yl)-1H-1,2,3-triazol-4-yl]methyl}quinazolin-4(3H)-one
aLaboratoire de Chimie Bio-organique et Macromoléculaire, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco, bLaboratoire de la Matière Condensée et des Nanostructures, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: m_elazhari52@yahoo.com
In the compound, C37H29N5O8, the quinazoline residue forms a dihedral angle of 72.90 (9)° with the triazole ring. The furan ring adopts a twist conformation. In the crystal, the molecules are linked by non-classical C—H⋯N and C—H⋯O hydrogen bonds, building an infinite three-dimensional network.
Related literature
For details of the synthesis, see: Ines et al. (2008); Krim et al. (2009); Huisgen (1963), Wu et al. (2004). For background to the biological activity of quinazolines, see: Traxler (1998); Bridges (2001); Wakeling (2005); Diana & Nitz (1993); Chen et al. (2000); Manfredini et al. (2000). For see: Cremer & Pople (1975).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812042778/bt6845sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042778/bt6845Isup2.hkl
The title compound, 3-((2,3,5-tri-O-benzoyl-β-D-ribofuranosyl- 1H-1,2,3-τriazol-4-yl)methyl) quinazolin-4(3H)-one was achieved by of propargylated quinazolinone with 2,3,5-tri-O-benzoyl-β-D– ribofuranosyl azide under microwave conditions with CuI as catalyst and without solvent. The product was obtained with quantitative yield (84%) and short reaction time (Ines et al. (2008); Krim et al. (2009)). The crude product was purified passing through a column packed with silica gel. Crystal suitable for X-ray analysis was obtained by slow evaporation of a methanol.
H atoms were located in a difference map and treated as riding with C—H = 0.97 Å and 0.93 Å for –CH2– and aromatic CH, respectively and with Uiso(H) = 1.2 Ueq(C). In the absence of significant
the could not be reliably determined and any references to the were removed.Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles. |
C37H29N5O8 | F(000) = 700 |
Mr = 671.65 | Dx = 1.381 Mg m−3 |
Monoclinic, P21 | Melting point: 454 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2646 (2) Å | Cell parameters from 4490 reflections |
b = 5.6471 (1) Å | θ = 0.8–28.5° |
c = 25.7507 (4) Å | µ = 0.10 mm−1 |
β = 99.595 (1)° | T = 296 K |
V = 1615.15 (5) Å3 | Block, colourless |
Z = 2 | 0.33 × 0.29 × 0.25 mm |
Bruker X8 APEXII diffractometer | 3651 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 28.5°, θmin = 0.8° |
ϕ and ω scans | h = −15→13 |
26180 measured reflections | k = −6→7 |
4490 independent reflections | l = −32→34 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0384P)2 + 0.1513P] where P = (Fo2 + 2Fc2)/3 |
4490 reflections | (Δ/σ)max = 0.001 |
451 parameters | Δρmax = 0.14 e Å−3 |
1 restraint | Δρmin = −0.13 e Å−3 |
C37H29N5O8 | V = 1615.15 (5) Å3 |
Mr = 671.65 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.2646 (2) Å | µ = 0.10 mm−1 |
b = 5.6471 (1) Å | T = 296 K |
c = 25.7507 (4) Å | 0.33 × 0.29 × 0.25 mm |
β = 99.595 (1)° |
Bruker X8 APEXII diffractometer | 3651 reflections with I > 2σ(I) |
26180 measured reflections | Rint = 0.029 |
4490 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 1 restraint |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.14 e Å−3 |
4490 reflections | Δρmin = −0.13 e Å−3 |
451 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.48779 (13) | 0.5193 (3) | 0.77079 (5) | 0.0599 (4) | |
C1 | 1.47437 (15) | 0.5402 (3) | 0.81663 (7) | 0.0394 (4) | |
C2 | 1.52690 (15) | 0.3864 (4) | 0.85969 (7) | 0.0409 (4) | |
C3 | 1.60106 (17) | 0.1978 (4) | 0.85044 (9) | 0.0527 (5) | |
H3 | 1.6160 | 0.1675 | 0.8166 | 0.063* | |
C4 | 1.6516 (2) | 0.0575 (5) | 0.89200 (12) | 0.0715 (7) | |
H4 | 1.7013 | −0.0682 | 0.8863 | 0.086* | |
C5 | 1.6288 (2) | 0.1029 (6) | 0.94223 (11) | 0.0803 (8) | |
H5 | 1.6638 | 0.0073 | 0.9700 | 0.096* | |
C6 | 1.5565 (2) | 0.2845 (6) | 0.95168 (9) | 0.0702 (7) | |
H6 | 1.5421 | 0.3122 | 0.9857 | 0.084* | |
C7 | 1.50357 (18) | 0.4298 (4) | 0.91030 (8) | 0.0491 (5) | |
N1 | 1.42881 (18) | 0.6125 (4) | 0.92126 (7) | 0.0596 (5) | |
N2 | 1.40433 (13) | 0.7224 (3) | 0.83175 (6) | 0.0419 (3) | |
C8 | 1.38486 (19) | 0.7462 (4) | 0.88269 (8) | 0.0545 (5) | |
H8 | 1.3355 | 0.8701 | 0.8898 | 0.065* | |
C9 | 1.35481 (18) | 0.8972 (4) | 0.79210 (8) | 0.0517 (5) | |
H9A | 1.4119 | 0.9228 | 0.7683 | 0.062* | |
H9B | 1.3444 | 1.0464 | 0.8095 | 0.062* | |
C10 | 1.23629 (16) | 0.8228 (3) | 0.76079 (7) | 0.0407 (4) | |
C11 | 1.18997 (17) | 0.6052 (4) | 0.74762 (8) | 0.0445 (4) | |
H11 | 1.2253 | 0.4588 | 0.7566 | 0.053* | |
N3 | 1.15628 (14) | 0.9885 (3) | 0.73967 (6) | 0.0439 (4) | |
N4 | 1.06111 (14) | 0.8827 (3) | 0.71381 (7) | 0.0456 (4) | |
N5 | 1.08115 (13) | 0.6486 (3) | 0.71851 (6) | 0.0392 (3) | |
C12 | 0.98816 (16) | 0.4739 (3) | 0.69944 (7) | 0.0396 (4) | |
H12 | 1.0233 | 0.3450 | 0.6815 | 0.048* | |
O2 | 0.93768 (11) | 0.3821 (3) | 0.74159 (5) | 0.0486 (3) | |
C13 | 0.81906 (16) | 0.4779 (4) | 0.74176 (7) | 0.0441 (4) | |
H13 | 0.7602 | 0.3536 | 0.7298 | 0.053* | |
C14 | 0.80732 (18) | 0.5416 (5) | 0.79708 (8) | 0.0529 (5) | |
H14A | 0.7273 | 0.6033 | 0.7979 | 0.063* | |
H14B | 0.8185 | 0.4013 | 0.8191 | 0.063* | |
C15 | 0.92262 (17) | 0.7284 (4) | 0.87000 (7) | 0.0495 (5) | |
O3 | 0.89576 (12) | 0.7166 (3) | 0.81724 (5) | 0.0523 (4) | |
O4 | 0.87382 (16) | 0.6050 (4) | 0.89822 (6) | 0.0759 (5) | |
C16 | 1.01456 (17) | 0.9096 (4) | 0.88883 (7) | 0.0482 (5) | |
C17 | 1.05099 (19) | 1.0778 (4) | 0.85589 (8) | 0.0537 (5) | |
H17 | 1.0199 | 1.0759 | 0.8201 | 0.064* | |
C18 | 1.1337 (2) | 1.2490 (5) | 0.87610 (10) | 0.0701 (7) | |
H18 | 1.1572 | 1.3638 | 0.8540 | 0.084* | |
C19 | 1.1811 (2) | 1.2495 (6) | 0.92904 (10) | 0.0770 (8) | |
H19 | 1.2372 | 1.3641 | 0.9425 | 0.092* | |
C20 | 1.1460 (3) | 1.0813 (7) | 0.96195 (10) | 0.0810 (8) | |
H20 | 1.1786 | 1.0821 | 0.9976 | 0.097* | |
C21 | 1.0629 (2) | 0.9123 (6) | 0.94236 (8) | 0.0688 (7) | |
H21 | 1.0389 | 0.7995 | 0.9648 | 0.083* | |
C22 | 0.80514 (15) | 0.6720 (3) | 0.70008 (7) | 0.0388 (4) | |
H22 | 0.8349 | 0.8231 | 0.7158 | 0.047* | |
O5 | 0.68225 (11) | 0.6958 (2) | 0.67425 (5) | 0.0454 (3) | |
O6 | 0.65640 (13) | 0.9904 (3) | 0.72934 (6) | 0.0625 (4) | |
C23 | 0.61705 (16) | 0.8669 (4) | 0.69278 (7) | 0.0420 (4) | |
C24 | 0.49230 (16) | 0.8815 (4) | 0.66316 (7) | 0.0440 (4) | |
C25 | 0.4252 (2) | 1.0813 (5) | 0.67048 (9) | 0.0592 (6) | |
H25 | 0.4599 | 1.2044 | 0.6918 | 0.071* | |
C26 | 0.3065 (2) | 1.0963 (6) | 0.64598 (11) | 0.0767 (9) | |
H26 | 0.2615 | 1.2304 | 0.6506 | 0.092* | |
C27 | 0.2555 (2) | 0.9163 (7) | 0.61522 (12) | 0.0833 (10) | |
H27 | 0.1751 | 0.9266 | 0.5995 | 0.100* | |
C28 | 0.3214 (2) | 0.7190 (7) | 0.60707 (11) | 0.0827 (9) | |
H28 | 0.2860 | 0.5976 | 0.5855 | 0.099* | |
C29 | 0.4405 (2) | 0.7013 (5) | 0.63111 (9) | 0.0620 (6) | |
H29 | 0.4855 | 0.5682 | 0.6256 | 0.074* | |
C30 | 0.88453 (15) | 0.5871 (4) | 0.66172 (7) | 0.0400 (4) | |
H30 | 0.9110 | 0.7159 | 0.6408 | 0.048* | |
O7 | 0.82166 (11) | 0.4025 (3) | 0.62974 (5) | 0.0452 (3) | |
O8 | 0.97436 (13) | 0.3887 (4) | 0.58366 (6) | 0.0704 (5) | |
C31 | 0.87760 (18) | 0.3172 (4) | 0.59115 (8) | 0.0494 (5) | |
C32 | 0.80817 (18) | 0.1250 (4) | 0.56099 (7) | 0.0486 (5) | |
C33 | 0.6908 (2) | 0.0733 (5) | 0.56586 (9) | 0.0645 (6) | |
H33 | 0.6516 | 0.1623 | 0.5883 | 0.077* | |
C34 | 0.6317 (3) | −0.1120 (6) | 0.53723 (10) | 0.0793 (8) | |
H34 | 0.5524 | −0.1467 | 0.5402 | 0.095* | |
C35 | 0.6900 (3) | −0.2449 (6) | 0.50442 (10) | 0.0794 (8) | |
H35 | 0.6503 | −0.3700 | 0.4854 | 0.095* | |
C36 | 0.8059 (3) | −0.1932 (6) | 0.49975 (10) | 0.0810 (9) | |
H36 | 0.8450 | −0.2836 | 0.4776 | 0.097* | |
C37 | 0.8650 (2) | −0.0097 (6) | 0.52735 (9) | 0.0666 (7) | |
H37 | 0.9438 | 0.0251 | 0.5236 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0670 (9) | 0.0774 (11) | 0.0363 (7) | 0.0054 (9) | 0.0121 (6) | 0.0024 (7) |
C1 | 0.0354 (9) | 0.0417 (10) | 0.0403 (9) | −0.0081 (8) | 0.0036 (7) | −0.0004 (8) |
C2 | 0.0346 (8) | 0.0445 (10) | 0.0420 (9) | −0.0090 (8) | 0.0021 (7) | 0.0018 (8) |
C3 | 0.0383 (10) | 0.0541 (13) | 0.0657 (13) | −0.0055 (9) | 0.0085 (9) | −0.0017 (11) |
C4 | 0.0495 (12) | 0.0572 (15) | 0.105 (2) | 0.0085 (11) | 0.0051 (12) | 0.0176 (15) |
C5 | 0.0767 (16) | 0.082 (2) | 0.0746 (17) | 0.0064 (16) | −0.0094 (13) | 0.0320 (16) |
C6 | 0.0818 (16) | 0.0797 (18) | 0.0457 (12) | −0.0010 (15) | 0.0006 (11) | 0.0169 (13) |
C7 | 0.0509 (11) | 0.0548 (13) | 0.0394 (10) | −0.0091 (10) | 0.0012 (8) | 0.0036 (9) |
N1 | 0.0744 (12) | 0.0659 (12) | 0.0388 (9) | 0.0013 (11) | 0.0105 (8) | −0.0050 (9) |
N2 | 0.0447 (8) | 0.0390 (8) | 0.0394 (8) | −0.0056 (7) | −0.0005 (6) | 0.0015 (7) |
C8 | 0.0628 (12) | 0.0528 (13) | 0.0472 (11) | 0.0010 (11) | 0.0075 (9) | −0.0084 (10) |
C9 | 0.0548 (11) | 0.0391 (11) | 0.0561 (12) | −0.0088 (10) | −0.0059 (9) | 0.0077 (9) |
C10 | 0.0464 (10) | 0.0327 (10) | 0.0417 (10) | −0.0007 (8) | 0.0032 (8) | 0.0027 (8) |
C11 | 0.0437 (10) | 0.0319 (9) | 0.0529 (11) | 0.0057 (8) | −0.0068 (8) | 0.0032 (9) |
N3 | 0.0439 (8) | 0.0296 (7) | 0.0580 (10) | 0.0008 (7) | 0.0074 (7) | 0.0036 (7) |
N4 | 0.0409 (8) | 0.0308 (8) | 0.0638 (10) | 0.0030 (7) | 0.0050 (7) | 0.0048 (8) |
N5 | 0.0400 (8) | 0.0290 (8) | 0.0467 (8) | 0.0026 (6) | 0.0018 (6) | 0.0008 (6) |
C12 | 0.0410 (9) | 0.0318 (9) | 0.0445 (10) | 0.0010 (8) | 0.0027 (7) | −0.0018 (8) |
O2 | 0.0480 (7) | 0.0437 (7) | 0.0533 (8) | 0.0039 (7) | 0.0059 (6) | 0.0130 (7) |
C13 | 0.0394 (9) | 0.0440 (10) | 0.0472 (10) | −0.0087 (9) | 0.0022 (7) | 0.0005 (9) |
C14 | 0.0479 (10) | 0.0664 (14) | 0.0444 (10) | −0.0136 (10) | 0.0075 (8) | 0.0057 (10) |
C15 | 0.0486 (10) | 0.0630 (13) | 0.0374 (10) | 0.0065 (10) | 0.0088 (8) | 0.0042 (10) |
O3 | 0.0546 (8) | 0.0639 (9) | 0.0369 (7) | −0.0138 (7) | 0.0028 (6) | 0.0009 (7) |
O4 | 0.0871 (11) | 0.0960 (14) | 0.0462 (8) | −0.0236 (12) | 0.0156 (8) | 0.0069 (10) |
C16 | 0.0489 (10) | 0.0554 (12) | 0.0395 (10) | 0.0059 (10) | 0.0048 (8) | −0.0042 (9) |
C17 | 0.0584 (12) | 0.0580 (13) | 0.0451 (11) | 0.0031 (11) | 0.0095 (9) | −0.0044 (10) |
C18 | 0.0831 (16) | 0.0657 (16) | 0.0636 (15) | −0.0101 (14) | 0.0185 (12) | −0.0084 (13) |
C19 | 0.0741 (16) | 0.088 (2) | 0.0684 (16) | −0.0170 (16) | 0.0097 (13) | −0.0245 (16) |
C20 | 0.0841 (17) | 0.106 (2) | 0.0478 (13) | −0.0097 (18) | −0.0033 (12) | −0.0182 (16) |
C21 | 0.0778 (15) | 0.0861 (19) | 0.0405 (11) | −0.0056 (15) | 0.0037 (10) | 0.0000 (12) |
C22 | 0.0349 (8) | 0.0389 (10) | 0.0408 (9) | 0.0000 (8) | 0.0009 (7) | −0.0039 (8) |
O5 | 0.0380 (6) | 0.0471 (8) | 0.0482 (7) | 0.0065 (6) | −0.0011 (5) | −0.0111 (6) |
O6 | 0.0558 (8) | 0.0545 (9) | 0.0761 (10) | −0.0015 (8) | 0.0079 (7) | −0.0252 (9) |
C23 | 0.0429 (9) | 0.0365 (10) | 0.0474 (10) | −0.0012 (8) | 0.0098 (8) | −0.0019 (9) |
C24 | 0.0411 (9) | 0.0481 (11) | 0.0443 (10) | 0.0030 (9) | 0.0116 (8) | 0.0094 (9) |
C25 | 0.0582 (12) | 0.0618 (14) | 0.0616 (13) | 0.0162 (12) | 0.0215 (10) | 0.0190 (12) |
C26 | 0.0622 (15) | 0.095 (2) | 0.0780 (17) | 0.0330 (16) | 0.0267 (13) | 0.0387 (17) |
C27 | 0.0468 (13) | 0.123 (3) | 0.0780 (18) | 0.0130 (17) | 0.0044 (12) | 0.048 (2) |
C28 | 0.0629 (15) | 0.095 (2) | 0.0812 (18) | −0.0118 (16) | −0.0149 (13) | 0.0114 (17) |
C29 | 0.0522 (12) | 0.0651 (15) | 0.0647 (14) | −0.0008 (12) | −0.0019 (10) | 0.0026 (12) |
C30 | 0.0417 (9) | 0.0388 (10) | 0.0385 (9) | 0.0017 (8) | 0.0040 (7) | −0.0005 (8) |
O7 | 0.0436 (7) | 0.0520 (8) | 0.0394 (7) | −0.0014 (6) | 0.0051 (5) | −0.0093 (6) |
O8 | 0.0559 (9) | 0.0925 (13) | 0.0672 (10) | −0.0132 (10) | 0.0234 (7) | −0.0204 (10) |
C31 | 0.0494 (11) | 0.0585 (13) | 0.0404 (10) | 0.0063 (10) | 0.0076 (8) | −0.0048 (9) |
C32 | 0.0521 (11) | 0.0568 (12) | 0.0355 (9) | 0.0057 (10) | 0.0034 (8) | −0.0033 (9) |
C33 | 0.0683 (14) | 0.0726 (16) | 0.0567 (13) | −0.0108 (13) | 0.0225 (11) | −0.0148 (13) |
C34 | 0.0811 (17) | 0.089 (2) | 0.0725 (16) | −0.0296 (17) | 0.0256 (14) | −0.0197 (16) |
C35 | 0.102 (2) | 0.0711 (18) | 0.0631 (15) | −0.0160 (17) | 0.0086 (14) | −0.0229 (14) |
C36 | 0.0784 (17) | 0.096 (2) | 0.0663 (15) | 0.0148 (16) | 0.0043 (13) | −0.0357 (16) |
C37 | 0.0544 (12) | 0.0889 (19) | 0.0549 (13) | 0.0114 (13) | 0.0043 (10) | −0.0217 (13) |
O1—C1 | 1.220 (2) | C17—C18 | 1.383 (3) |
C1—N2 | 1.391 (2) | C17—H17 | 0.9300 |
C1—C2 | 1.455 (3) | C18—C19 | 1.379 (4) |
C2—C7 | 1.394 (3) | C18—H18 | 0.9300 |
C2—C3 | 1.398 (3) | C19—C20 | 1.374 (4) |
C3—C4 | 1.376 (3) | C19—H19 | 0.9300 |
C3—H3 | 0.9300 | C20—C21 | 1.373 (4) |
C4—C5 | 1.384 (4) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.357 (4) | C22—O5 | 1.439 (2) |
C5—H5 | 0.9300 | C22—C30 | 1.517 (2) |
C6—C7 | 1.397 (3) | C22—H22 | 0.9800 |
C6—H6 | 0.9300 | O5—C23 | 1.348 (2) |
C7—N1 | 1.390 (3) | O6—C23 | 1.196 (2) |
N1—C8 | 1.280 (3) | C23—C24 | 1.485 (3) |
N2—C8 | 1.372 (2) | C24—C29 | 1.377 (3) |
N2—C9 | 1.462 (3) | C24—C25 | 1.388 (3) |
C8—H8 | 0.9300 | C25—C26 | 1.383 (3) |
C9—C10 | 1.500 (3) | C25—H25 | 0.9300 |
C9—H9A | 0.9700 | C26—C27 | 1.356 (5) |
C9—H9B | 0.9700 | C26—H26 | 0.9300 |
C10—N3 | 1.349 (2) | C27—C28 | 1.374 (5) |
C10—C11 | 1.356 (3) | C27—H27 | 0.9300 |
C11—N5 | 1.348 (2) | C28—C29 | 1.385 (3) |
C11—H11 | 0.9300 | C28—H28 | 0.9300 |
N3—N4 | 1.308 (2) | C29—H29 | 0.9300 |
N4—N5 | 1.343 (2) | C30—O7 | 1.439 (2) |
N5—C12 | 1.463 (2) | C30—H30 | 0.9800 |
C12—O2 | 1.406 (2) | O7—C31 | 1.351 (2) |
C12—C30 | 1.529 (2) | O8—C31 | 1.207 (2) |
C12—H12 | 0.9800 | C31—C32 | 1.480 (3) |
O2—C13 | 1.442 (2) | C32—C33 | 1.380 (3) |
C13—C14 | 1.496 (3) | C32—C37 | 1.387 (3) |
C13—C22 | 1.524 (3) | C33—C34 | 1.385 (4) |
C13—H13 | 0.9800 | C33—H33 | 0.9300 |
C14—O3 | 1.437 (3) | C34—C35 | 1.376 (4) |
C14—H14A | 0.9700 | C34—H34 | 0.9300 |
C14—H14B | 0.9700 | C35—C36 | 1.362 (4) |
C15—O4 | 1.204 (3) | C35—H35 | 0.9300 |
C15—O3 | 1.343 (2) | C36—C37 | 1.365 (4) |
C15—C16 | 1.479 (3) | C36—H36 | 0.9300 |
C16—C17 | 1.381 (3) | C37—H37 | 0.9300 |
C16—C21 | 1.395 (3) | ||
O1—C1—N2 | 120.65 (17) | C16—C17—C18 | 120.0 (2) |
O1—C1—C2 | 125.40 (18) | C16—C17—H17 | 120.0 |
N2—C1—C2 | 113.95 (16) | C18—C17—H17 | 120.0 |
C7—C2—C3 | 120.29 (19) | C19—C18—C17 | 120.0 (3) |
C7—C2—C1 | 119.44 (18) | C19—C18—H18 | 120.0 |
C3—C2—C1 | 120.26 (18) | C17—C18—H18 | 120.0 |
C4—C3—C2 | 119.2 (2) | C20—C19—C18 | 120.3 (3) |
C4—C3—H3 | 120.4 | C20—C19—H19 | 119.9 |
C2—C3—H3 | 120.4 | C18—C19—H19 | 119.9 |
C3—C4—C5 | 120.2 (2) | C21—C20—C19 | 120.2 (2) |
C3—C4—H4 | 119.9 | C21—C20—H20 | 119.9 |
C5—C4—H4 | 119.9 | C19—C20—H20 | 119.9 |
C6—C5—C4 | 121.2 (2) | C20—C21—C16 | 120.1 (3) |
C6—C5—H5 | 119.4 | C20—C21—H21 | 120.0 |
C4—C5—H5 | 119.4 | C16—C21—H21 | 120.0 |
C5—C6—C7 | 120.0 (2) | O5—C22—C30 | 110.78 (13) |
C5—C6—H6 | 120.0 | O5—C22—C13 | 111.78 (15) |
C7—C6—H6 | 120.0 | C30—C22—C13 | 103.22 (16) |
N1—C7—C2 | 122.38 (18) | O5—C22—H22 | 110.3 |
N1—C7—C6 | 118.5 (2) | C30—C22—H22 | 110.3 |
C2—C7—C6 | 119.1 (2) | C13—C22—H22 | 110.3 |
C8—N1—C7 | 116.71 (17) | C23—O5—C22 | 116.25 (14) |
C8—N2—C1 | 121.92 (17) | O6—C23—O5 | 122.97 (17) |
C8—N2—C9 | 119.88 (18) | O6—C23—C24 | 124.52 (18) |
C1—N2—C9 | 118.16 (16) | O5—C23—C24 | 112.50 (16) |
N1—C8—N2 | 125.5 (2) | C29—C24—C25 | 119.8 (2) |
N1—C8—H8 | 117.2 | C29—C24—C23 | 122.45 (19) |
N2—C8—H8 | 117.2 | C25—C24—C23 | 117.7 (2) |
N2—C9—C10 | 112.83 (17) | C26—C25—C24 | 119.7 (3) |
N2—C9—H9A | 109.0 | C26—C25—H25 | 120.2 |
C10—C9—H9A | 109.0 | C24—C25—H25 | 120.2 |
N2—C9—H9B | 109.0 | C27—C26—C25 | 120.3 (3) |
C10—C9—H9B | 109.0 | C27—C26—H26 | 119.9 |
H9A—C9—H9B | 107.8 | C25—C26—H26 | 119.9 |
N3—C10—C11 | 108.93 (16) | C26—C27—C28 | 120.6 (2) |
N3—C10—C9 | 119.82 (17) | C26—C27—H27 | 119.7 |
C11—C10—C9 | 131.24 (18) | C28—C27—H27 | 119.7 |
N5—C11—C10 | 104.50 (17) | C27—C28—C29 | 119.9 (3) |
N5—C11—H11 | 127.7 | C27—C28—H28 | 120.1 |
C10—C11—H11 | 127.7 | C29—C28—H28 | 120.1 |
N4—N3—C10 | 108.91 (16) | C24—C29—C28 | 119.8 (3) |
N3—N4—N5 | 107.01 (15) | C24—C29—H29 | 120.1 |
N4—N5—C11 | 110.65 (16) | C28—C29—H29 | 120.1 |
N4—N5—C12 | 122.23 (15) | O7—C30—C22 | 108.31 (14) |
C11—N5—C12 | 126.70 (16) | O7—C30—C12 | 108.15 (15) |
O2—C12—N5 | 110.41 (14) | C22—C30—C12 | 100.90 (14) |
O2—C12—C30 | 106.29 (14) | O7—C30—H30 | 112.9 |
N5—C12—C30 | 111.07 (15) | C22—C30—H30 | 112.9 |
O2—C12—H12 | 109.7 | C12—C30—H30 | 112.9 |
N5—C12—H12 | 109.7 | C31—O7—C30 | 115.70 (15) |
C30—C12—H12 | 109.7 | O8—C31—O7 | 122.9 (2) |
C12—O2—C13 | 110.98 (14) | O8—C31—C32 | 124.97 (19) |
O2—C13—C14 | 108.78 (15) | O7—C31—C32 | 112.15 (17) |
O2—C13—C22 | 104.75 (14) | C33—C32—C37 | 119.3 (2) |
C14—C13—C22 | 118.86 (19) | C33—C32—C31 | 122.55 (19) |
O2—C13—H13 | 108.0 | C37—C32—C31 | 118.14 (19) |
C14—C13—H13 | 108.0 | C32—C33—C34 | 119.6 (2) |
C22—C13—H13 | 108.0 | C32—C33—H33 | 120.2 |
O3—C14—C13 | 110.08 (15) | C34—C33—H33 | 120.2 |
O3—C14—H14A | 109.6 | C35—C34—C33 | 120.2 (2) |
C13—C14—H14A | 109.6 | C35—C34—H34 | 119.9 |
O3—C14—H14B | 109.6 | C33—C34—H34 | 119.9 |
C13—C14—H14B | 109.6 | C36—C35—C34 | 120.0 (3) |
H14A—C14—H14B | 108.2 | C36—C35—H35 | 120.0 |
O4—C15—O3 | 122.2 (2) | C34—C35—H35 | 120.0 |
O4—C15—C16 | 124.62 (18) | C35—C36—C37 | 120.5 (2) |
O3—C15—C16 | 113.16 (17) | C35—C36—H36 | 119.7 |
C15—O3—C14 | 115.17 (16) | C37—C36—H36 | 119.7 |
C17—C16—C21 | 119.5 (2) | C36—C37—C32 | 120.4 (2) |
C17—C16—C15 | 122.56 (17) | C36—C37—H37 | 119.8 |
C21—C16—C15 | 117.9 (2) | C32—C37—H37 | 119.8 |
O1—C1—C2—C7 | −179.64 (19) | O3—C15—C16—C21 | −170.2 (2) |
N2—C1—C2—C7 | 0.4 (2) | C21—C16—C17—C18 | −0.8 (3) |
O1—C1—C2—C3 | 0.9 (3) | C15—C16—C17—C18 | 177.3 (2) |
N2—C1—C2—C3 | −178.99 (16) | C16—C17—C18—C19 | 1.0 (4) |
C7—C2—C3—C4 | −0.7 (3) | C17—C18—C19—C20 | −0.5 (4) |
C1—C2—C3—C4 | 178.7 (2) | C18—C19—C20—C21 | −0.3 (5) |
C2—C3—C4—C5 | 0.2 (4) | C19—C20—C21—C16 | 0.5 (4) |
C3—C4—C5—C6 | 0.2 (4) | C17—C16—C21—C20 | 0.0 (4) |
C4—C5—C6—C7 | −0.1 (4) | C15—C16—C21—C20 | −178.1 (2) |
C3—C2—C7—N1 | −178.85 (19) | O2—C13—C22—O5 | 147.77 (14) |
C1—C2—C7—N1 | 1.7 (3) | C14—C13—C22—O5 | −90.54 (19) |
C3—C2—C7—C6 | 0.8 (3) | O2—C13—C22—C30 | 28.67 (18) |
C1—C2—C7—C6 | −178.6 (2) | C14—C13—C22—C30 | 150.35 (16) |
C5—C6—C7—N1 | 179.3 (2) | C30—C22—O5—C23 | −148.57 (16) |
C5—C6—C7—C2 | −0.4 (4) | C13—C22—O5—C23 | 96.90 (19) |
C2—C7—N1—C8 | −2.3 (3) | C22—O5—C23—O6 | −1.7 (3) |
C6—C7—N1—C8 | 178.0 (2) | C22—O5—C23—C24 | 178.91 (16) |
O1—C1—N2—C8 | 178.11 (19) | O6—C23—C24—C29 | −162.5 (2) |
C2—C1—N2—C8 | −2.0 (2) | O5—C23—C24—C29 | 16.9 (3) |
O1—C1—N2—C9 | −4.4 (3) | O6—C23—C24—C25 | 14.6 (3) |
C2—C1—N2—C9 | 175.55 (15) | O5—C23—C24—C25 | −166.00 (16) |
C7—N1—C8—N2 | 0.8 (3) | C29—C24—C25—C26 | 0.7 (3) |
C1—N2—C8—N1 | 1.5 (3) | C23—C24—C25—C26 | −176.40 (19) |
C9—N2—C8—N1 | −176.0 (2) | C24—C25—C26—C27 | 0.4 (3) |
C8—N2—C9—C10 | −95.6 (2) | C25—C26—C27—C28 | −1.3 (4) |
C1—N2—C9—C10 | 86.8 (2) | C26—C27—C28—C29 | 1.0 (4) |
N2—C9—C10—N3 | 152.32 (18) | C25—C24—C29—C28 | −1.0 (3) |
N2—C9—C10—C11 | −28.9 (3) | C23—C24—C29—C28 | 176.0 (2) |
N3—C10—C11—N5 | −0.2 (2) | C27—C28—C29—C24 | 0.1 (4) |
C9—C10—C11—N5 | −179.07 (19) | O5—C22—C30—O7 | −42.7 (2) |
C11—C10—N3—N4 | 0.2 (2) | C13—C22—C30—O7 | 77.08 (16) |
C9—C10—N3—N4 | 179.22 (17) | O5—C22—C30—C12 | −156.17 (15) |
C10—N3—N4—N5 | −0.1 (2) | C13—C22—C30—C12 | −36.37 (17) |
N3—N4—N5—C11 | 0.0 (2) | O2—C12—C30—O7 | −81.39 (17) |
N3—N4—N5—C12 | 173.02 (15) | N5—C12—C30—O7 | 158.48 (14) |
C10—C11—N5—N4 | 0.1 (2) | O2—C12—C30—C22 | 32.19 (18) |
C10—C11—N5—C12 | −172.54 (17) | N5—C12—C30—C22 | −87.95 (17) |
N4—N5—C12—O2 | −101.9 (2) | C22—C30—O7—C31 | 176.14 (16) |
C11—N5—C12—O2 | 70.0 (2) | C12—C30—O7—C31 | −75.31 (19) |
N4—N5—C12—C30 | 15.8 (2) | C30—O7—C31—O8 | 0.3 (3) |
C11—N5—C12—C30 | −172.38 (17) | C30—O7—C31—C32 | 178.77 (15) |
N5—C12—O2—C13 | 105.43 (16) | O8—C31—C32—C33 | −170.3 (2) |
C30—C12—O2—C13 | −15.1 (2) | O7—C31—C32—C33 | 11.3 (3) |
C12—O2—C13—C14 | −136.61 (18) | O8—C31—C32—C37 | 10.9 (3) |
C12—O2—C13—C22 | −8.5 (2) | O7—C31—C32—C37 | −167.5 (2) |
O2—C13—C14—O3 | 60.5 (2) | C37—C32—C33—C34 | 0.1 (4) |
C22—C13—C14—O3 | −59.1 (2) | C31—C32—C33—C34 | −178.7 (2) |
O4—C15—O3—C14 | −1.7 (3) | C32—C33—C34—C35 | 0.5 (4) |
C16—C15—O3—C14 | 179.56 (18) | C33—C34—C35—C36 | −0.5 (5) |
C13—C14—O3—C15 | −157.97 (19) | C34—C35—C36—C37 | −0.1 (5) |
O4—C15—C16—C17 | −167.0 (2) | C35—C36—C37—C32 | 0.7 (4) |
O3—C15—C16—C17 | 11.7 (3) | C33—C32—C37—C36 | −0.7 (4) |
O4—C15—C16—C21 | 11.1 (3) | C31—C32—C37—C36 | 178.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O6i | 0.93 | 2.57 | 3.483 (3) | 168 |
C13—H13···O6ii | 0.98 | 2.36 | 3.293 (3) | 159 |
C6—H6···N1iii | 0.93 | 2.62 | 3.390 (3) | 141 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y−1, z; (iii) −x+3, y−1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C37H29N5O8 |
Mr | 671.65 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 11.2646 (2), 5.6471 (1), 25.7507 (4) |
β (°) | 99.595 (1) |
V (Å3) | 1615.15 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.33 × 0.29 × 0.25 |
Data collection | |
Diffractometer | Bruker X8 APEXII diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26180, 4490, 3651 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.671 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.081, 1.03 |
No. of reflections | 4490 |
No. of parameters | 451 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.13 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia,1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O6i | 0.93 | 2.57 | 3.483 (3) | 167.7 |
C13—H13···O6ii | 0.98 | 2.36 | 3.293 (3) | 158.9 |
C6—H6···N1iii | 0.93 | 2.62 | 3.390 (3) | 140.7 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y−1, z; (iii) −x+3, y−1/2, −z+2. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Quinazoline and its derivatives are an interesting class of heterocyclic compounds that have drawn much attention because of their biological and pharmaceutical activities including a wide range of antitumor activity (Traxler, 1998; Bridges, 2001; Wakeling, 2005). Furthermore, triazole heterocycles are potent antiviral (Diana & Nitz, 1993), antimicrobial (Chen et al., 2000), and anti-proliferate agents (Manfredini et al., 2000). The pharmaceutical importance of triazoles has prompted the design and synthesis of various triazolonucleosides.
The most interesting method for the synthesis of triazoles is the Huisgen 1,3-dipolar cycloaddition of organic azides with alkynes (Huisgen, 1963). Copper-catalyzed click chemistry is an efficient method that uses azides and terminal acetylenes to have 1,4-disubstituted-1,2,3- triazole products with excellent selectivity and high yield (Wu et al., 2004). In connection to our studies on the synthesis of new nucleosides, we decided to explore the feasibility of the 'click' chemistry for the synthesis of novel 1,2,3-triazoles containing the quinazolinone moiety.
The molecule of the title compound contains a quinazolinone moiety linked to a furan ring through a triazole ring. As shown in Fig.1, the furan ring is also connected to three benzoyl rings. The furan ring which adopts a twist conformation as indicated by Cremer & Pople (1975) puckering parameters Q(2)= 0.365 (2) Å and the phase angle ϕ = 85.7 (3)°. The five-membered ring (O2 C12 C13 C22 C30) is nearly perpendicular to (N3 N4 N5 C10 C11), (C16 to C21), (C24 to C29) and to (C32 to C37) with the dihedral angles of 79.6 (2), 75.9 (2), 83.4 (2) and 88.2 (2)°, respectively.
An intermolecular C–H···N and C–H···O non classic hydrogen bonds, building an infinite three-dimensional network ensure the cohesion of the crystal structure (see Table 1).