2,3-Di­methyl­quinazolin-4(3H)-one

Saitkulov, F.E.; Tashniyazov, A.A.; Mamadrahimov, A.A.; Shakhidoyatov, K.M.

doi:10.1107/S1600536814013749

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 7| July 2014| Page o788

https://doi.org/10.1107/S1600536814013749

Open

access

2,3-Dimethylquinazolin-4(3H)-one

Fozil E. Saitkulov,^a ^* Azamat A. Tashniyazov,^b Azimjon A. Mamadrahimov ^c and Kh. M. Shakhidoyatov ^d

^aAlisher Navoi Samarkand State University, Ministry of Higher and Secondary Special Education, University Avenue 15, Samarkand 703004, Uzbekistan, ^bMirzo Ulugbek National University of Uzbekistan, Faculty of Chemistry, University St 6, Tashkent 100779, Uzbekistan, ^cInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, Mirzo Ulugbek St 83, Tashkent 100125, Uzbekistan, and ^dS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek St, 77, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: f.saitkulov@mail.ru

(Received 2 June 2014; accepted 12 June 2014; online 18 June 2014)

The non-H atoms of the title molecule, C₁₀H₁₀N₂O, are essentially coplanar, with a maximum deviation of 0.046 (4) Å for the O atom. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming chains along [010]. In addtion, weak C—H⋯π interactions and π–π stacking interactions between benzene and pyrimidine rings, with a centroid–centroid distance of 3.730 (3) Å, link the chains, forming a two-dimensional network parallel to (001).

CCDC reference: 1007927

Related literature

For the synthesis of related compounds, see: Takeuchi & Eguchi (1989 ). For the crystal structure of a related compound, see: Makhloufi et al. (2013 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₀H₁₀N₂O
M_r = 174.20
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.826 (2) Å
b = 7.919 (3) Å
c = 23.060 (8) Å
V = 881.3 (11) Å³
Z = 4
Cu Kα radiation
μ = 0.71 mm⁻¹
T = 293 K
0.40 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.041, T_max = 1.000
2236 measured reflections
1585 independent reflections
821 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.230
S = 0.97
1585 reflections
121 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 507 Friedel pairs
Absolute structure parameter: −0.3 (12)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/C2/N3/C4/C4A/C8A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1ⁱ	0.96	2.47	3.345 (8)	151
C10—H10B⋯Cgⁱⁱ	0.96	2.80	3.608 (6)	142
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1007927

Crystal structure: contains datablocks I, GLOBAL. DOI: https://doi.org/10.1107/S1600536814013749/lh5714sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013749/lh5714Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013749/lh5714Isup3.cml

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig .1. The non-H atoms are essentially co-planar, with a maximum deviation of 0.046 (4) Å for atom O1. In the crystal, molecules are linked by weak C—H···O hydrogen bonds to form chains along [010] (Fig. 2). In addition, weak C—H···π interactions and π–π stacking interactions between benzene and pyrimidine rings with a centroid–centroid distance of 3.730 (3)Å, link chains forming a two-dimensional network parallel to (001). The bond distances (Allen et al., 1987) and angles are in normal ranges. The crystal structure of a related cation is reported in the literature (Makhloufi et al., 2013) and the synthesis of compounds related to the title compound is described by (Takeuchi & Eguchi, 1989).

Related literature top

For the synthesis of related compounds, see: Takeuchi & Eguchi (1989). For the crystal structure of a related compound, see: Makhloufi et al. (2013). For standard bond lengths, see: Allen et al. (1987).

Experimental top

2-Methylquinazolin-4-one (0.01) mol was disolved in 45 ml absolute ethanol, then 2.5 mmol of NaH was added and then shaken for 30 min. To the reaction mixture was added solution of 0.01 mol methyliodide in 5 ml ethanol and the reaction mixture was refluxed for 4 h at 363 K. To this mixture was added 100 ml of cold water and then extracted with chloroform. The title compound was obtained in 69% yield with m.p. 491 K. Crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the title compound in ethanol.

Structure description top

For the synthesis of related compounds, see: Takeuchi & Eguchi (1989). For the crystal structure of a related compound, see: Makhloufi et al. (2013). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound showing a hydrogen bonds as dashed lines.

2,3-Dimethylquinazolin-4(3H)-one top

Crystal data top

C₁₀H₁₀N₂O	D_x = 1.313 Mg m⁻³
M_r = 174.20	Melting point: 491(2) K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 333 reflections
a = 4.826 (2) Å	θ = 3.8–64.0°
b = 7.919 (3) Å	µ = 0.71 mm⁻¹
c = 23.060 (8) Å	T = 293 K
V = 881.3 (11) Å³	Needle, colourless
Z = 4	0.40 × 0.10 × 0.08 mm
F(000) = 368

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	1585 independent reflections
Radiation source: fine-focus sealed tube	821 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 10.2576 pixels mm^-1	θ_max = 75.9°, θ_min = 3.8°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −5→9
T_min = 0.041, T_max = 1.000	l = −28→28
2236 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.071	H-atom parameters constrained
wR(F²) = 0.230	w = 1/[σ²(F_o²) + (0.1116P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
1585 reflections	Δρ_max = 0.20 e Å⁻³
121 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 507 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.3 (12)

Crystal data top

C₁₀H₁₀N₂O	V = 881.3 (11) Å³
M_r = 174.20	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 4.826 (2) Å	µ = 0.71 mm⁻¹
b = 7.919 (3) Å	T = 293 K
c = 23.060 (8) Å	0.40 × 0.10 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	1585 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	821 reflections with I > 2σ(I)
T_min = 0.041, T_max = 1.000	R_int = 0.020
2236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	H-atom parameters constrained
wR(F²) = 0.230	Δρ_max = 0.20 e Å⁻³
S = 0.97	Δρ_min = −0.19 e Å⁻³
1585 reflections	Absolute structure: Flack (1983), 507 Friedel pairs
121 parameters	Absolute structure parameter: −0.3 (12)
0 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

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

	x	y	z	U_iso*/U_eq
N3	0.3333 (9)	−0.1245 (5)	0.17512 (17)	0.0819 (12)
O1	0.4020 (9)	0.1511 (4)	0.19869 (17)	0.1055 (13)
N1	0.5799 (9)	−0.2643 (5)	0.10074 (17)	0.0846 (11)
C4A	0.6580 (10)	0.0357 (6)	0.1199 (2)	0.0773 (13)
C4	0.4620 (11)	0.0295 (7)	0.1667 (2)	0.0807 (13)
C10	0.1309 (12)	−0.1350 (7)	0.2233 (2)	0.1009 (17)
H10A	0.2040	−0.2059	0.2534	0.151*
H10B	−0.0397	−0.1819	0.2093	0.151*
H10C	0.0975	−0.0240	0.2386	0.151*
C8	0.8983 (11)	−0.1088 (7)	0.0431 (2)	0.0912 (15)
H8	0.9313	−0.2067	0.0219	0.109*
C2	0.4000 (11)	−0.2650 (6)	0.1422 (2)	0.0816 (13)
C8A	0.7099 (9)	−0.1120 (6)	0.0883 (2)	0.0769 (12)
C7	1.0368 (13)	0.0367 (8)	0.0292 (2)	0.1023 (16)
H7	1.1647	0.0374	−0.0010	0.123*
C9	0.2541 (14)	−0.4274 (7)	0.1551 (3)	0.109 (2)
H9A	0.2779	−0.4552	0.1954	0.164*
H9B	0.3305	−0.5158	0.1316	0.164*
H9C	0.0603	−0.4153	0.1468	0.164*
C6	0.9842 (12)	0.1838 (7)	0.0607 (3)	0.1019 (18)
H6	1.0776	0.2828	0.0514	0.122*
C5	0.7965 (12)	0.1837 (6)	0.1051 (2)	0.0923 (16)
H5	0.7615	0.2828	0.1255	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N3	0.077 (2)	0.080 (3)	0.089 (3)	0.004 (2)	0.003 (2)	0.002 (2)
O1	0.118 (3)	0.083 (2)	0.115 (3)	0.008 (2)	−0.002 (3)	−0.024 (2)
N1	0.080 (2)	0.080 (2)	0.094 (3)	−0.004 (2)	0.002 (2)	−0.005 (2)
C4A	0.074 (3)	0.072 (3)	0.086 (3)	−0.001 (2)	−0.011 (3)	−0.001 (3)
C4	0.083 (3)	0.073 (3)	0.086 (3)	0.010 (3)	−0.011 (3)	−0.004 (3)
C10	0.100 (4)	0.104 (4)	0.098 (3)	0.020 (4)	0.012 (3)	0.008 (3)
C8	0.085 (3)	0.090 (3)	0.099 (3)	0.004 (3)	0.003 (3)	−0.012 (3)
C2	0.076 (3)	0.066 (3)	0.102 (3)	0.004 (3)	−0.006 (3)	−0.002 (3)
C8A	0.068 (3)	0.071 (3)	0.091 (3)	−0.001 (3)	−0.005 (3)	0.003 (3)
C7	0.092 (4)	0.117 (4)	0.098 (3)	−0.003 (4)	0.006 (3)	0.006 (4)
C9	0.103 (4)	0.077 (3)	0.147 (5)	−0.002 (3)	0.014 (4)	0.002 (4)
C6	0.096 (4)	0.092 (4)	0.118 (4)	−0.013 (3)	−0.008 (4)	0.022 (3)
C5	0.093 (4)	0.076 (3)	0.108 (4)	0.003 (3)	−0.009 (3)	−0.002 (3)

Geometric parameters (Å, º) top

N3—C4	1.382 (6)	C8—C7	1.370 (7)
N3—C2	1.385 (6)	C8—C8A	1.383 (7)
N3—C10	1.482 (6)	C8—H8	0.9300
O1—C4	1.248 (6)	C2—C9	1.496 (7)
N1—C2	1.292 (6)	C7—C6	1.397 (8)
N1—C8A	1.390 (6)	C7—H7	0.9300
C4A—C5	1.392 (7)	C9—H9A	0.9600
C4A—C8A	1.400 (6)	C9—H9B	0.9600
C4A—C4	1.436 (7)	C9—H9C	0.9600
C10—H10A	0.9600	C6—C5	1.368 (7)
C10—H10B	0.9600	C6—H6	0.9300
C10—H10C	0.9600	C5—H5	0.9300

C4—N3—C2	121.8 (4)	N1—C2—C9	117.9 (5)
C4—N3—C10	116.8 (4)	N3—C2—C9	118.2 (5)
C2—N3—C10	121.3 (5)	C8—C8A—N1	117.9 (5)
C2—N1—C8A	117.4 (4)	C8—C8A—C4A	119.6 (5)
C5—C4A—C8A	119.4 (5)	N1—C8A—C4A	122.4 (4)
C5—C4A—C4	121.9 (5)	C8—C7—C6	119.4 (5)
C8A—C4A—C4	118.7 (5)	C8—C7—H7	120.3
O1—C4—N3	119.5 (5)	C6—C7—H7	120.3
O1—C4—C4A	124.9 (5)	C2—C9—H9A	109.5
N3—C4—C4A	115.6 (4)	C2—C9—H9B	109.5
N3—C10—H10A	109.5	H9A—C9—H9B	109.5
N3—C10—H10B	109.5	C2—C9—H9C	109.5
H10A—C10—H10B	109.5	H9A—C9—H9C	109.5
N3—C10—H10C	109.5	H9B—C9—H9C	109.5
H10A—C10—H10C	109.5	C5—C6—C7	120.7 (5)
H10B—C10—H10C	109.5	C5—C6—H6	119.7
C7—C8—C8A	120.8 (5)	C7—C6—H6	119.7
C7—C8—H8	119.6	C6—C5—C4A	120.1 (5)
C8A—C8—H8	119.6	C6—C5—H5	120.0
N1—C2—N3	124.0 (5)	C4A—C5—H5	120.0

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N1/C2/N3/C4/C4A/C8A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1ⁱ	0.96	2.47	3.345 (8)	151
C10—H10B···Cgⁱⁱ	0.96	2.80	3.608 (6)	142

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N1/C2/N3/C4/C4A/C8A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1ⁱ	0.96	2.47	3.345 (8)	151
C10—H10B···Cgⁱⁱ	0.96	2.80	3.608 (6)	142

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z.

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F7–T185).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Makhloufi, A., Wahl, M., Frank, W. & Ganter, C. (2013). Organometallics, 32, 854–861. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takeuchi, H. & Eguchi, S. (1989). Tetrahedron Lett. 30, 3313–3314. CrossRef CAS Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 7| July 2014| Page o788

https://doi.org/10.1107/S1600536814013749

Open

access