organic compounds
S,2S)-3-methyl-2-phenyl-2,3-dihydrothiazolo[2,3-b]quinazolin-5-one
of (1aMedicinal, Aromatic and Poisonous Plants Research Center, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, bDepartment of Pharmacognosy, College of Pharmacy, Salman Bin Abdulaziz University, PO Box 173, Al-Kharji 1194, Saudi Arabia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
The 17H14N2OS, was determined by the of the to 0.0 (2) based on 1011 Friedel pairs. The quinazoline ring is essentially planar, with a maximum deviation of 0.037 (2) Å. The thiazole ring is distorted from planarity [maximum deviation = 0.168 (2) Å] and adopts a slightly twisted with the C atom as the flap atom. The central thiazole ring makes dihedral angles of 7.01 (8) and 76.80 (10)° with the quinazoline and phenyl rings, respectively. The corresponding angle between the quinazoline and phenyl rings is 3.74 (9)°. In the crystal, there are no classical hydrogen bonds but stabilization is provided by weak C—H⋯π interactions, involving the centroids of the phenyl rings.
of the molecule in the crystal of the title compound, CRelated literature
For details and applications of quinazoline derivatives, see: Ghorab et al. (2010a,b,c). For related crystal structures, see: Al-Salahi et al. (2012); Priya et al. (2011); Liu et al. (2010). For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S160053681200832X/nk2145sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681200832X/nk2145Isup2.hkl
A mixture of 2-isothiocyanatobenzoate (1.93 g, 0.01 mole) and 2-amino-1-phenylpropan-1-ol (1.51 g, 0.01 mole) in dry dimethylformamide (30 ml) containing a catalytic amount of triethylamine was refluxed for 6 h. The solid obtained was recrystallized from ethanol to give the title thiazoloquinazline derivative compound. Single crystals suitable for X-ray structural analysis were obtained by slow evaporation from ethanol at room temperature.
All H atoms were positioned geometrically [C—H = 0.93–0.98 Å] and were refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl groups. 1011 Friedel pairs were used to determine the absolute configuration.
Quinazoline derivatives are well known as biologically active compounds. Consequently, quinazolines have been intensively studied for their interesting pharmacological properties such as anticancer activity (Ghorab et al., 2010a,b,c). The crystal structures of 2-Ethoxy-5-methylbis[1,2,4]triazolo[1,5-a:4',3'-c] quinazoline (Al-Salahi et al., 2012), 3-(4-Chlorophenyl)quinazolin-4(3H)-one (Priya et al., 2011) and 2-Anilino-3-(2-hydroxyphenyl)quinazolin-4(3H)-one methanol monosolvate (Liu et al., 2010) have been reported in the literature. Herein, we report the
of title compound (I).The θ = 226.7 (4)° (Cremer & Pople, 1975). The central thiazole (S1/N1/C1–C2,C10) ring makes dihedral angles of 7.01 (8)° and 76.80 (10)° with the quinazoline (N1,N2/C3–C10) and phenyl (C11–C16) rings, respectively. The corresponding angle between the quinazoline (N1,N2/C3–C10) and phenyl (C11–C16) rings is 73.74 (9)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges.
of the title compound is shown in Fig. 1. The quinazoline (N1,N2/C3–C10) ring is essentially planar, with a maximum deviation of 0.037 (2) Å for atom C8. The thiazole (S1/N2/C7–C9) rings adopt an with the C2 (0.168 (2) Å) atom as the flap atom and with puckering parameter, Q = 0.2724 (19) Å andThe
of the molecule were determined by the of the to 0.0 (2). There are two chiral centres in the molecule. From the structure presented, these centers exhibit the following chiralities: C1 = S and C2 = S.In the π interactions (Table 1) involving the centroids of the (C4–C9) and (C11–C16) phenyl rings.
(Fig. 2), there are no classical hydrogen bonds but stabilization is provided by weak C—H···For details and applications of quinazoline derivatives, see: Ghorab et al. (2010a,b,c). For related crystal structures, see: Al-Salahi et al. (2012); Priya et al. (2011); Liu et al. (2010). For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. | |
Fig. 2. The crystal packing of the title compound (I). |
C17H14N2OS | F(000) = 616 |
Mr = 294.36 | Dx = 1.358 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4079 reflections |
a = 8.4865 (1) Å | θ = 4.4–71.7° |
b = 10.0846 (2) Å | µ = 1.99 mm−1 |
c = 16.8290 (3) Å | T = 296 K |
V = 1440.28 (4) Å3 | Block, colourless |
Z = 4 | 0.96 × 0.64 × 0.51 mm |
Bruker SMART APEXII CCD diffractometer | 2637 independent reflections |
Radiation source: fine-focus sealed tube | 2521 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 71.9°, θmin = 5.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −10→10 |
Tmin = 0.251, Tmax = 0.431 | k = −8→12 |
8654 measured reflections | l = −20→20 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0729P)2 + 0.0628P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max = 0.001 |
S = 1.08 | Δρmax = 0.22 e Å−3 |
2637 reflections | Δρmin = −0.23 e Å−3 |
192 parameters | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.107 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1011 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (2) |
C17H14N2OS | V = 1440.28 (4) Å3 |
Mr = 294.36 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 8.4865 (1) Å | µ = 1.99 mm−1 |
b = 10.0846 (2) Å | T = 296 K |
c = 16.8290 (3) Å | 0.96 × 0.64 × 0.51 mm |
Bruker SMART APEXII CCD diffractometer | 2637 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2521 reflections with I > 2σ(I) |
Tmin = 0.251, Tmax = 0.431 | Rint = 0.028 |
8654 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.109 | Δρmax = 0.22 e Å−3 |
S = 1.08 | Δρmin = −0.23 e Å−3 |
2637 reflections | Absolute structure: Flack (1983), with 1011 Friedel pairs |
192 parameters | Absolute structure parameter: 0.00 (2) |
0 restraints |
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 | ||
S1 | 0.93740 (6) | 0.77405 (8) | 0.26159 (3) | 0.0835 (3) | |
N1 | 0.84292 (17) | 0.75544 (18) | 0.40678 (9) | 0.0558 (4) | |
N2 | 0.99073 (19) | 0.57264 (18) | 0.35894 (9) | 0.0585 (4) | |
O1 | 0.7394 (3) | 0.7625 (3) | 0.53134 (11) | 0.0983 (7) | |
C3 | 0.8142 (2) | 0.7024 (3) | 0.48182 (12) | 0.0654 (5) | |
C10 | 0.9264 (2) | 0.6865 (2) | 0.35080 (10) | 0.0540 (4) | |
C9 | 0.9715 (2) | 0.51345 (19) | 0.43270 (11) | 0.0561 (4) | |
C12 | 0.5242 (2) | 0.8021 (2) | 0.28662 (15) | 0.0693 (6) | |
H12A | 0.5479 | 0.7496 | 0.3304 | 0.083* | |
C11 | 0.6379 (2) | 0.88563 (18) | 0.25601 (12) | 0.0556 (4) | |
C4 | 0.8811 (2) | 0.5710 (2) | 0.49297 (11) | 0.0598 (5) | |
C13 | 0.3752 (3) | 0.7954 (3) | 0.25291 (17) | 0.0743 (6) | |
H13A | 0.2993 | 0.7396 | 0.2746 | 0.089* | |
C5 | 0.8607 (3) | 0.5028 (3) | 0.56509 (14) | 0.0774 (6) | |
H5A | 0.8007 | 0.5405 | 0.6055 | 0.093* | |
C14 | 0.3400 (3) | 0.8704 (2) | 0.18807 (17) | 0.0730 (6) | |
H14A | 0.2396 | 0.8670 | 0.1660 | 0.088* | |
C16 | 0.6023 (3) | 0.9594 (2) | 0.18898 (14) | 0.0633 (5) | |
H16A | 0.6783 | 1.0144 | 0.1666 | 0.076* | |
C6 | 0.9290 (4) | 0.3807 (3) | 0.57612 (17) | 0.0875 (8) | |
H6A | 0.9131 | 0.3350 | 0.6235 | 0.105* | |
C1 | 0.7973 (2) | 0.9010 (2) | 0.29489 (15) | 0.0659 (5) | |
H1A | 0.8396 | 0.9878 | 0.2798 | 0.079* | |
C15 | 0.4533 (3) | 0.9515 (2) | 0.15507 (14) | 0.0723 (6) | |
H15A | 0.4299 | 1.0010 | 0.1100 | 0.087* | |
C8 | 1.0433 (3) | 0.3896 (2) | 0.44566 (15) | 0.0744 (6) | |
H8A | 1.1052 | 0.3517 | 0.4061 | 0.089* | |
C2 | 0.7980 (2) | 0.8926 (2) | 0.38635 (14) | 0.0659 (5) | |
H2B | 0.6911 | 0.9094 | 0.4060 | 0.079* | |
C17 | 0.9107 (4) | 0.9910 (3) | 0.4252 (3) | 0.1039 (11) | |
H17A | 0.9070 | 0.9806 | 0.4818 | 0.156* | |
H17C | 0.8802 | 1.0797 | 0.4113 | 0.156* | |
H17D | 1.0160 | 0.9746 | 0.4067 | 0.156* | |
C7 | 1.0225 (4) | 0.3247 (3) | 0.51644 (19) | 0.0874 (8) | |
H7A | 1.0707 | 0.2431 | 0.5248 | 0.105* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0541 (3) | 0.1285 (5) | 0.0680 (3) | 0.0297 (3) | 0.0168 (2) | 0.0362 (3) |
N1 | 0.0436 (7) | 0.0702 (9) | 0.0535 (8) | 0.0037 (6) | −0.0037 (6) | −0.0028 (7) |
N2 | 0.0529 (8) | 0.0726 (10) | 0.0500 (7) | 0.0055 (7) | −0.0055 (6) | −0.0051 (7) |
O1 | 0.1001 (14) | 0.1344 (18) | 0.0602 (9) | 0.0463 (14) | 0.0130 (8) | −0.0049 (10) |
C3 | 0.0512 (9) | 0.0952 (14) | 0.0497 (9) | 0.0092 (10) | −0.0022 (8) | −0.0043 (9) |
C10 | 0.0393 (7) | 0.0739 (11) | 0.0490 (8) | 0.0004 (7) | −0.0014 (7) | 0.0020 (7) |
C9 | 0.0526 (9) | 0.0635 (10) | 0.0522 (9) | −0.0071 (7) | −0.0092 (7) | −0.0034 (7) |
C12 | 0.0519 (10) | 0.0741 (12) | 0.0820 (13) | −0.0033 (8) | −0.0106 (9) | 0.0223 (10) |
C11 | 0.0469 (8) | 0.0523 (8) | 0.0675 (10) | 0.0055 (6) | −0.0032 (8) | 0.0022 (8) |
C4 | 0.0472 (8) | 0.0815 (12) | 0.0507 (9) | −0.0083 (8) | −0.0059 (7) | 0.0028 (8) |
C13 | 0.0491 (10) | 0.0816 (13) | 0.0923 (16) | −0.0055 (9) | −0.0084 (10) | 0.0104 (12) |
C5 | 0.0615 (12) | 0.1126 (18) | 0.0579 (11) | −0.0103 (12) | −0.0015 (9) | 0.0107 (12) |
C14 | 0.0527 (10) | 0.0768 (13) | 0.0896 (15) | 0.0096 (9) | −0.0178 (11) | −0.0050 (11) |
C16 | 0.0634 (11) | 0.0560 (9) | 0.0705 (11) | 0.0068 (8) | −0.0005 (9) | 0.0064 (8) |
C6 | 0.0857 (16) | 0.0934 (17) | 0.0833 (15) | −0.0174 (14) | −0.0132 (14) | 0.0307 (13) |
C1 | 0.0460 (9) | 0.0666 (10) | 0.0850 (14) | −0.0021 (8) | −0.0040 (9) | 0.0180 (10) |
C15 | 0.0745 (13) | 0.0697 (11) | 0.0727 (12) | 0.0158 (10) | −0.0151 (10) | 0.0056 (9) |
C8 | 0.0880 (15) | 0.0662 (11) | 0.0691 (11) | 0.0015 (11) | −0.0152 (12) | −0.0065 (9) |
C2 | 0.0505 (9) | 0.0676 (11) | 0.0795 (13) | 0.0061 (8) | −0.0114 (9) | −0.0047 (10) |
C17 | 0.0876 (19) | 0.0806 (16) | 0.143 (3) | −0.0012 (14) | −0.038 (2) | −0.0195 (18) |
C7 | 0.107 (2) | 0.0709 (13) | 0.0845 (15) | −0.0052 (13) | −0.0216 (15) | 0.0107 (11) |
S1—C10 | 1.7439 (18) | C5—C6 | 1.374 (5) |
S1—C1 | 1.835 (2) | C5—H5A | 0.9300 |
N1—C10 | 1.368 (3) | C14—C15 | 1.379 (4) |
N1—C3 | 1.393 (3) | C14—H14A | 0.9300 |
N1—C2 | 1.475 (3) | C16—C15 | 1.390 (3) |
N2—C10 | 1.279 (3) | C16—H16A | 0.9300 |
N2—C9 | 1.387 (3) | C6—C7 | 1.399 (5) |
O1—C3 | 1.211 (3) | C6—H6A | 0.9300 |
C3—C4 | 1.454 (3) | C1—C2 | 1.542 (3) |
C9—C4 | 1.398 (3) | C1—H1A | 0.9800 |
C9—C8 | 1.406 (3) | C15—H15A | 0.9300 |
C12—C11 | 1.380 (3) | C8—C7 | 1.371 (4) |
C12—C13 | 1.388 (3) | C8—H8A | 0.9300 |
C12—H12A | 0.9300 | C2—C17 | 1.526 (3) |
C11—C16 | 1.385 (3) | C2—H2B | 0.9800 |
C11—C1 | 1.511 (3) | C17—H17A | 0.9600 |
C4—C5 | 1.406 (3) | C17—H17C | 0.9600 |
C13—C14 | 1.361 (4) | C17—H17D | 0.9600 |
C13—H13A | 0.9300 | C7—H7A | 0.9300 |
C10—S1—C1 | 93.18 (10) | C11—C16—H16A | 119.9 |
C10—N1—C3 | 121.33 (18) | C15—C16—H16A | 119.9 |
C10—N1—C2 | 116.71 (17) | C5—C6—C7 | 120.3 (2) |
C3—N1—C2 | 121.72 (18) | C5—C6—H6A | 119.9 |
C10—N2—C9 | 115.61 (16) | C7—C6—H6A | 119.9 |
O1—C3—N1 | 121.6 (2) | C11—C1—C2 | 115.45 (17) |
O1—C3—C4 | 124.9 (2) | C11—C1—S1 | 112.12 (16) |
N1—C3—C4 | 113.49 (18) | C2—C1—S1 | 105.33 (14) |
N2—C10—N1 | 127.10 (17) | C11—C1—H1A | 107.9 |
N2—C10—S1 | 121.59 (14) | C2—C1—H1A | 107.9 |
N1—C10—S1 | 111.31 (14) | S1—C1—H1A | 107.9 |
N2—C9—C4 | 122.34 (19) | C14—C15—C16 | 120.2 (2) |
N2—C9—C8 | 118.0 (2) | C14—C15—H15A | 119.9 |
C4—C9—C8 | 119.6 (2) | C16—C15—H15A | 119.9 |
C11—C12—C13 | 120.9 (2) | C7—C8—C9 | 120.2 (3) |
C11—C12—H12A | 119.5 | C7—C8—H8A | 119.9 |
C13—C12—H12A | 119.5 | C9—C8—H8A | 119.9 |
C12—C11—C16 | 118.68 (18) | N1—C2—C17 | 110.36 (19) |
C12—C11—C1 | 121.78 (18) | N1—C2—C1 | 106.58 (17) |
C16—C11—C1 | 119.52 (18) | C17—C2—C1 | 113.2 (2) |
C9—C4—C5 | 119.4 (2) | N1—C2—H2B | 108.9 |
C9—C4—C3 | 119.94 (18) | C17—C2—H2B | 108.9 |
C5—C4—C3 | 120.6 (2) | C1—C2—H2B | 108.9 |
C14—C13—C12 | 120.0 (2) | C2—C17—H17A | 109.5 |
C14—C13—H13A | 120.0 | C2—C17—H17C | 109.5 |
C12—C13—H13A | 120.0 | H17A—C17—H17C | 109.5 |
C6—C5—C4 | 120.2 (3) | C2—C17—H17D | 109.5 |
C6—C5—H5A | 119.9 | H17A—C17—H17D | 109.5 |
C4—C5—H5A | 119.9 | H17C—C17—H17D | 109.5 |
C13—C14—C15 | 120.0 (2) | C8—C7—C6 | 120.3 (3) |
C13—C14—H14A | 120.0 | C8—C7—H7A | 119.8 |
C15—C14—H14A | 120.0 | C6—C7—H7A | 119.8 |
C11—C16—C15 | 120.1 (2) | ||
C10—N1—C3—O1 | −179.4 (2) | C3—C4—C5—C6 | −177.7 (2) |
C2—N1—C3—O1 | 6.4 (3) | C12—C13—C14—C15 | 1.1 (4) |
C10—N1—C3—C4 | 0.1 (3) | C12—C11—C16—C15 | 1.8 (3) |
C2—N1—C3—C4 | −174.12 (17) | C1—C11—C16—C15 | −176.6 (2) |
C9—N2—C10—N1 | 0.6 (3) | C4—C5—C6—C7 | 1.6 (4) |
C9—N2—C10—S1 | −179.34 (13) | C12—C11—C1—C2 | −34.8 (3) |
C3—N1—C10—N2 | −2.2 (3) | C16—C11—C1—C2 | 143.6 (2) |
C2—N1—C10—N2 | 172.28 (18) | C12—C11—C1—S1 | 85.8 (2) |
C3—N1—C10—S1 | 177.70 (15) | C16—C11—C1—S1 | −95.81 (19) |
C2—N1—C10—S1 | −7.8 (2) | C10—S1—C1—C11 | −105.81 (15) |
C1—S1—C10—N2 | 171.57 (16) | C10—S1—C1—C2 | 20.52 (15) |
C1—S1—C10—N1 | −8.37 (15) | C13—C14—C15—C16 | −1.6 (4) |
C10—N2—C9—C4 | 3.2 (3) | C11—C16—C15—C14 | 0.1 (3) |
C10—N2—C9—C8 | −178.35 (18) | N2—C9—C8—C7 | −177.4 (2) |
C13—C12—C11—C16 | −2.4 (4) | C4—C9—C8—C7 | 1.2 (3) |
C13—C12—C11—C1 | 176.0 (2) | C10—N1—C2—C17 | −99.9 (3) |
N2—C9—C4—C5 | 177.15 (19) | C3—N1—C2—C17 | 74.6 (3) |
C8—C9—C4—C5 | −1.3 (3) | C10—N1—C2—C1 | 23.4 (2) |
N2—C9—C4—C3 | −5.2 (3) | C3—N1—C2—C1 | −162.12 (17) |
C8—C9—C4—C3 | 176.33 (19) | C11—C1—C2—N1 | 97.6 (2) |
O1—C3—C4—C9 | −177.2 (2) | S1—C1—C2—N1 | −26.69 (19) |
N1—C3—C4—C9 | 3.3 (3) | C11—C1—C2—C17 | −140.9 (2) |
O1—C3—C4—C5 | 0.4 (4) | S1—C1—C2—C17 | 94.8 (2) |
N1—C3—C4—C5 | −179.06 (19) | C9—C8—C7—C6 | 0.3 (4) |
C11—C12—C13—C14 | 0.9 (4) | C5—C6—C7—C8 | −1.7 (4) |
C9—C4—C5—C6 | 0.0 (3) |
Cg3 and Cg4 are the centroids of the C4–C9 and C11–C16 phenyl rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···Cg3i | 0.98 | 2.91 | 3.824 (2) | 155 |
C6—H6A···Cg4ii | 0.93 | 2.81 | 3.637 (3) | 146 |
Symmetry codes: (i) −x−1, y+3/2, −z+3/2; (ii) −x+3/2, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H14N2OS |
Mr | 294.36 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 8.4865 (1), 10.0846 (2), 16.8290 (3) |
V (Å3) | 1440.28 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.99 |
Crystal size (mm) | 0.96 × 0.64 × 0.51 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.251, 0.431 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8654, 2637, 2521 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.109, 1.08 |
No. of reflections | 2637 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.23 |
Absolute structure | Flack (1983), with 1011 Friedel pairs |
Absolute structure parameter | 0.00 (2) |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg3 and Cg4 are the centroids of the C4–C9 and C11–C16 phenyl rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···Cg3i | 0.98 | 2.91 | 3.824 (2) | 155.00 |
C6—H6A···Cg4ii | 0.93 | 2.81 | 3.637 (3) | 146.00 |
Symmetry codes: (i) −x−1, y+3/2, −z+3/2; (ii) −x+3/2, −y+1, z+1/2. |
Footnotes
‡Alternative address: College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.
Acknowledgements
MMG, MSA and MSA are grateful for sponsorship of the Research Center, College of Pharmacy, and the Deanship of Scientific Research, King Saud University, Riyadh, Saudia Arabia. MH and HFK thank the Malaysian Government and Universiti Sains Malaysia for Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a postdoctoral research fellowship.
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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 derivatives are well known as biologically active compounds. Consequently, quinazolines have been intensively studied for their interesting pharmacological properties such as anticancer activity (Ghorab et al., 2010a,b,c). The crystal structures of 2-Ethoxy-5-methylbis[1,2,4]triazolo[1,5-a:4',3'-c] quinazoline (Al-Salahi et al., 2012), 3-(4-Chlorophenyl)quinazolin-4(3H)-one (Priya et al., 2011) and 2-Anilino-3-(2-hydroxyphenyl)quinazolin-4(3H)-one methanol monosolvate (Liu et al., 2010) have been reported in the literature. Herein, we report the crystal structure of title compound (I).
The asymmetric unit of the title compound is shown in Fig. 1. The quinazoline (N1,N2/C3–C10) ring is essentially planar, with a maximum deviation of 0.037 (2) Å for atom C8. The thiazole (S1/N2/C7–C9) rings adopt an envelope conformation with the C2 (0.168 (2) Å) atom as the flap atom and with puckering parameter, Q = 0.2724 (19) Å and θ = 226.7 (4)° (Cremer & Pople, 1975). The central thiazole (S1/N1/C1–C2,C10) ring makes dihedral angles of 7.01 (8)° and 76.80 (10)° with the quinazoline (N1,N2/C3–C10) and phenyl (C11–C16) rings, respectively. The corresponding angle between the quinazoline (N1,N2/C3–C10) and phenyl (C11–C16) rings is 73.74 (9)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges.
The absolute configuration of the molecule were determined by the refinement of the Flack parameter to 0.0 (2). There are two chiral centres in the molecule. From the structure presented, these centers exhibit the following chiralities: C1 = S and C2 = S.
In the crystal structure (Fig. 2), there are no classical hydrogen bonds but stabilization is provided by weak C—H···π interactions (Table 1) involving the centroids of the (C4–C9) and (C11–C16) phenyl rings.