Redetermination at 113 K of 2,2-tetra­methyl­ene-1,2-dihydro­quinazolin-4(3H)-one

Zhang, L.; Li, J.; Shi, D.; Chen, J.

doi:10.1107/S1600536807066706

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o449

doi:10.1107/S1600536807066706

Open

access

Redetermination at 113 K of 2,2-tetramethylene-1,2-dihydroquinazolin-4(3H)-one

Lijun Zhang,^a Jiarong Li,^a ^* Daxin Shi ^a and Jinnan Chen ^a

^aSchool of Chemical Engineering and the Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
^*Correspondence e-mail: jrli@bit.edu.cn

(Received 20 November 2007; accepted 12 December 2007; online 16 January 2008)

The title compound {systematic name: spiro[cyclopentane-1,2′(1′H)-quinazolin]-4′(3′H)-one]}, C₁₂H₁₄N₂O, has been reported previously [Klemm, Weakley, Gilbertson & Song (1998 ). J. Heterocycl Chem. 35, 1269–1273]. Its structure has been redetermined at 113 K with greater precision for all data. The molecule is built up from two fused six-membered rings and one five-membered ring linked through a spiro C atom. The pyrimidine ring has an envelope conformation and the cyclopentane ring adopts a distorted boat form. There are intermolecular N—H⋯O hydrogen bonds, which form a two-dimensional sheet parallel to the (001) plane.

Related literature

For related literature, see: Bernstein et al. (1995 ); Cremer & Pople (1975 ); Etter et al. (1990 ); Shi et al. (2004 ); Summers et al. (1986 ).

Experimental

Crystal data

C₁₂H₁₄N₂O
M_r = 202.25
Orthorhombic, P b c a
a = 10.3872 (12) Å
b = 12.0252 (13) Å
c = 16.3027 (19) Å
V = 2036.3 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 113 (2) K
0.26 × 0.24 × 0.16 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.972, T_max = 0.984
23533 measured reflections
2403 independent reflections
2200 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.104
S = 1.09
2403 reflections
142 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.857 (9)	2.043 (9)	2.8936 (12)	171.2 (14)
N2—H2⋯O1ⁱⁱ	0.857 (9)	2.077 (9)	2.9303 (13)	173.3 (14)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku, 2004 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807066706/dn2298sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807066706/dn2298Isup2.hkl

checkCIF report

Comment top

When we used 2-aminobenzonitrile and cyclopentanone in presence of zinc chloride to synthesize tacrine (Summers et al., 1986) derivative, the unexpected spiro compound (I) (Scheme 1), was obtained. Its structure has been already reported (Klemm et al., 1998), however, as we were investigating the molecular and supramolecular architecture of related compounds, its structural redetermination at lower temperature (113 K) has been undertaken

The molecular structure of (I) is built up with two fused six membered ring and a five membered ring linked through a spiro C atom (Fig. 1). The pyrimidine ring has an envelope conformation with puckering parameters Q=0.3821 (11) Å, Θ= 115.21 (16)° and ϕ= 108.70 (19)° (Cremer & Pople, 1975). The five-membered ring displays an enveloppe conformation at C12 with puckering parameters Q(2)= O.3925 (15)Å and ϕ(2)= 319.8 (2)\%. The geometry of the fused rings compares well with the related 3-phenyl-1,2-dihydroquinazolin-4(3H)-one derivative (Shi et al., 2004).

The crystal structure of (I) is stabilized by the interplay of N—H···O interactions. The two N—H groups form N—H···O hydrogen bonds with the ketone O atom of symmetry related molecules building a R₂²(8) graph set motif (Etter et al., 1990; Bernstein et al., 1995). Those motifs formed with N—H···O hydrogen bonds link to each other building a two dimensionnal network parallel to the (0 0 1) plane (Fig. 2, Table 1).

Related literature top

For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975); Etter et al. (1990); Shi et al. (2004); Summers et al. (1986).

Experimental top

2,2-Tetramethylene-1,2-dihydroquinazolin-4(3H)-one (I) was prepared from the reflux of 2-aminobenzonitrile (1 mmol) with cyclopentanone (1 mmol) in presence of zinc chloride (1.2 mmol) in 10 ml DMF for 1.5 h. Then the reaction mixture was cooled and quenched with water and the precipitate was separated by filtration. The filtration residue was dispersed into water and titrated to pH 12–13 by 20% sodium hydroxide. After filtration, the product was obtained in 70% yield by column chromatography (200–300 mesh silica gel, ethyl acetate–petroleum with 1:2).

The single-crystal of (I) was cultured from a solution of ethanol by slow evaporation at room temperature.

Spectra data: IR (KBr, cm^-1): 3289, 3166, 2934, 1638, 1613, 1429; ¹H NMR (DMSO-d₆) δ_H: 1.75–2.08 (8H, m, C₄H₈), 6.07 (1H, s, NH), 6.73 (2H, dd, J=7.8, 8.0 Hz, ArH), 7.19 (1H, s, NH), 7.24–7.26 (1H, m, J=7.2 Hz, ArH), 7.73 (1H, d, J=8.0 Hz, ArH); ¹³C NMR (DMSO-d₆) δ_C: 21.97 (2 C), 38.88 (2 C), 77.05, 114.32, 114.57, 116.53, 127.23, 132.99, 147.49, 163.42; MS (ESI): m/z (%) =203.1 (100) [M+H]⁺; C₁₂H₁₄N₂O: calcd. C 71.26, H 6.98, N 13.85; found C 71.38, H 6.71, N 13.49.

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. The molecular structure of (I), with the atom-labelling scheme. Displacement elipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing showing one sheet of molecules connected by N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bondings have been omitted for clarity.

spiro[cyclopentane-1,2'(1'H)-quinazolin]-4'(3'H)-one] top

Crystal data top

C₁₂H₁₄N₂O	F(000) = 864
M_r = 202.25	D_x = 1.319 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5598 reflections
a = 10.3872 (12) Å	θ = 2.6–27.9°
b = 12.0252 (13) Å	µ = 0.09 mm⁻¹
c = 16.3027 (19) Å	T = 113 K
V = 2036.3 (4) Å³	Prism, colorless
Z = 8	0.26 × 0.24 × 0.16 mm

Data collection top

Rigaku Saturn diffractometer	2403 independent reflections
Radiation source: rotating anode	2200 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.033
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.9°
ω scans	h = −13→13
Absorption correction: multi-scan (Jacobson, 1998)	k = −15→15
T_min = 0.972, T_max = 0.984	l = −21→21
23533 measured reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0476P)² + 0.9123P] where P = (F_o² + 2F_c²)/3
2403 reflections	(Δ/σ)_max = 0.001
142 parameters	Δρ_max = 0.31 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₂H₁₄N₂O	V = 2036.3 (4) Å³
M_r = 202.25	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.3872 (12) Å	µ = 0.09 mm⁻¹
b = 12.0252 (13) Å	T = 113 K
c = 16.3027 (19) Å	0.26 × 0.24 × 0.16 mm

Data collection top

Rigaku Saturn diffractometer	2403 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2200 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.984	R_int = 0.033
23533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	2 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.31 e Å⁻³
2403 reflections	Δρ_min = −0.23 e Å⁻³
142 parameters

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
O1	0.08554 (8)	0.58043 (6)	0.58072 (5)	0.01704 (19)
N1	0.14762 (9)	0.42225 (8)	0.51639 (6)	0.0162 (2)
H1	0.0821 (11)	0.4272 (12)	0.4846 (8)	0.019*
N2	0.30566 (10)	0.30494 (8)	0.57191 (6)	0.0176 (2)
H2	0.3437 (13)	0.2417 (9)	0.5745 (9)	0.021*
C1	0.27524 (10)	0.48724 (9)	0.62879 (6)	0.0149 (2)
C2	0.34067 (10)	0.38442 (9)	0.62795 (7)	0.0155 (2)
C3	0.43548 (11)	0.36400 (10)	0.68791 (7)	0.0189 (2)
H3	0.4778	0.2959	0.6891	0.023*
C4	0.46564 (11)	0.44475 (10)	0.74485 (7)	0.0208 (3)
H4	0.5295	0.4308	0.7835	0.025*
C5	0.40171 (12)	0.54737 (10)	0.74554 (7)	0.0210 (3)
H5	0.4232	0.6013	0.7840	0.025*
C6	0.30602 (11)	0.56750 (9)	0.68820 (7)	0.0186 (2)
H6	0.2618	0.6347	0.6891	0.022*
C7	0.16430 (10)	0.50191 (9)	0.57324 (7)	0.0144 (2)
C8	0.24515 (11)	0.33881 (9)	0.49553 (6)	0.0148 (2)
C9	0.18435 (11)	0.23692 (10)	0.45265 (7)	0.0182 (2)
H9A	0.1703	0.1774	0.4918	0.022*
H9B	0.1023	0.2568	0.4283	0.022*
C10	0.27944 (13)	0.20002 (11)	0.38614 (9)	0.0300 (3)
H10A	0.3038	0.1229	0.3942	0.036*
H10B	0.2410	0.2075	0.3322	0.036*
C11	0.39717 (12)	0.27571 (10)	0.39391 (8)	0.0229 (3)
H11A	0.4620	0.2424	0.4290	0.027*
H11B	0.4348	0.2906	0.3406	0.027*
C12	0.34353 (11)	0.38216 (10)	0.43211 (7)	0.0195 (2)
H12A	0.3019	0.4282	0.3911	0.023*
H12B	0.4111	0.4248	0.4585	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0156 (4)	0.0139 (4)	0.0217 (4)	0.0012 (3)	−0.0010 (3)	−0.0011 (3)
N1	0.0137 (4)	0.0154 (4)	0.0194 (5)	0.0023 (3)	−0.0038 (4)	−0.0026 (4)
N2	0.0213 (5)	0.0138 (5)	0.0178 (5)	0.0050 (4)	−0.0044 (4)	−0.0006 (4)
C1	0.0145 (5)	0.0152 (5)	0.0149 (5)	−0.0015 (4)	0.0004 (4)	0.0010 (4)
C2	0.0144 (5)	0.0165 (5)	0.0155 (5)	−0.0010 (4)	0.0016 (4)	0.0010 (4)
C3	0.0180 (5)	0.0210 (5)	0.0178 (5)	0.0034 (4)	0.0003 (4)	0.0027 (4)
C4	0.0179 (5)	0.0287 (6)	0.0157 (5)	−0.0010 (5)	−0.0031 (4)	0.0020 (5)
C5	0.0231 (6)	0.0220 (6)	0.0180 (5)	−0.0051 (5)	−0.0032 (4)	−0.0020 (4)
C6	0.0204 (6)	0.0161 (5)	0.0194 (6)	−0.0017 (4)	−0.0002 (4)	−0.0007 (4)
C7	0.0140 (5)	0.0132 (5)	0.0159 (5)	−0.0015 (4)	0.0018 (4)	0.0015 (4)
C8	0.0141 (5)	0.0134 (5)	0.0168 (5)	0.0015 (4)	−0.0010 (4)	−0.0008 (4)
C9	0.0164 (5)	0.0171 (5)	0.0212 (5)	−0.0009 (4)	−0.0007 (4)	−0.0035 (4)
C10	0.0310 (7)	0.0266 (7)	0.0324 (7)	−0.0065 (5)	0.0113 (6)	−0.0128 (5)
C11	0.0196 (6)	0.0256 (6)	0.0235 (6)	0.0013 (5)	0.0037 (5)	−0.0038 (5)
C12	0.0199 (6)	0.0187 (6)	0.0198 (5)	−0.0028 (4)	0.0021 (4)	0.0002 (4)

Geometric parameters (Å, º) top

O1—C7	1.2553 (13)	C5—H5	0.9300
N1—C7	1.3442 (14)	C6—H6	0.9300
N1—C8	1.4659 (14)	C8—C12	1.5443 (15)
N1—H1	0.857 (9)	C8—C9	1.5456 (15)
N2—C2	1.3712 (15)	C9—C10	1.5323 (17)
N2—C8	1.4531 (14)	C9—H9A	0.9700
N2—H2	0.857 (9)	C9—H9B	0.9700
C1—C6	1.4041 (15)	C10—C11	1.5297 (17)
C1—C2	1.4110 (15)	C10—H10A	0.9700
C1—C7	1.4762 (15)	C10—H10B	0.9700
C2—C3	1.4091 (16)	C11—C12	1.5287 (17)
C3—C4	1.3794 (16)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.4014 (17)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.3857 (16)

C7—N1—C8	123.96 (9)	N1—C8—C12	112.43 (9)
C7—N1—H1	118.0 (9)	N2—C8—C9	110.01 (9)
C8—N1—H1	117.1 (10)	N1—C8—C9	111.42 (9)
C2—N2—C8	119.36 (9)	C12—C8—C9	103.60 (9)
C2—N2—H2	117.6 (10)	C10—C9—C8	106.63 (9)
C8—N2—H2	119.3 (10)	C10—C9—H9A	110.4
C6—C1—C2	119.95 (10)	C8—C9—H9A	110.4
C6—C1—C7	121.25 (10)	C10—C9—H9B	110.4
C2—C1—C7	118.35 (10)	C8—C9—H9B	110.4
N2—C2—C3	121.74 (10)	H9A—C9—H9B	108.6
N2—C2—C1	119.31 (10)	C11—C10—C9	106.53 (10)
C3—C2—C1	118.85 (10)	C11—C10—H10A	110.4
C4—C3—C2	120.19 (11)	C9—C10—H10A	110.4
C4—C3—H3	119.9	C11—C10—H10B	110.4
C2—C3—H3	119.9	C9—C10—H10B	110.4
C3—C4—C5	121.17 (11)	H10A—C10—H10B	108.6
C3—C4—H4	119.4	C12—C11—C10	103.92 (10)
C5—C4—H4	119.4	C12—C11—H11A	111.0
C6—C5—C4	119.23 (11)	C10—C11—H11A	111.0
C6—C5—H5	120.4	C12—C11—H11B	111.0
C4—C5—H5	120.4	C10—C11—H11B	111.0
C5—C6—C1	120.57 (11)	H11A—C11—H11B	109.0
C5—C6—H6	119.7	C11—C12—C8	103.37 (9)
C1—C6—H6	119.7	C11—C12—H12A	111.1
O1—C7—N1	121.26 (10)	C8—C12—H12A	111.1
O1—C7—C1	122.62 (10)	C11—C12—H12B	111.1
N1—C7—C1	116.01 (9)	C8—C12—H12B	111.1
N2—C8—N1	106.98 (9)	H12A—C12—H12B	109.1
N2—C8—C12	112.46 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86 (1)	2.04 (1)	2.8936 (12)	171 (1)
N2—H2···O1ⁱⁱ	0.86 (1)	2.08 (1)	2.9303 (13)	173 (1)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₂O
M_r	202.25
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	113
a, b, c (Å)	10.3872 (12), 12.0252 (13), 16.3027 (19)
V (Å³)	2036.3 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.24 × 0.16

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.972, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	23533, 2403, 2200
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.104, 1.09
No. of reflections	2403
No. of parameters	142
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.857 (9)	2.043 (9)	2.8936 (12)	171.2 (14)
N2—H2···O1ⁱⁱ	0.857 (9)	2.077 (9)	2.9303 (13)	173.3 (14)

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

Acknowledgements

We thank Beijing Institute of Technology for financial support and Naikai University for the X-ray diffraction analysis.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jacobson, R. (1998). Private communication to Rigaku Corporation, Tokyo, Japan. Google Scholar
Klemm, L. H., Weakley, T. J. R., Gilbertson, R. D. & Song, Y. H. (1998). J. Heterocycl. Chem. 35, 1269–1273. CrossRef CAS Google Scholar
Rigaku (2004). CrystalClear. Version 1.36. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Shi, D. Q., Rong, L. C., Wang, J. X., Wang, X. S., Tu, S. J. & Hu, H. W. (2004). Chem. J. Chin. Univ. 25, 2051–2053. CAS Google Scholar
Summers, W. K., Majovski, L. V., Marsh, G. M., Tachiki, K. & Kling, A. (1986). N. Engl. J. Med. 315, 1241–1245. CrossRef CAS PubMed Web of Science Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. 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 64| Part 2| February 2008| Page o449

doi:10.1107/S1600536807066706

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Redetermination at 113 K of 2,2-tetra­methyl­ene-1,2-di­hydro­quinazolin-4(3H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Redetermination at 113 K of 2,2-tetramethylene-1,2-dihydroquinazolin-4(3H)-one