Literature DB >> 26396813

Crystal structure of 3-amino-2-propyl-quinazolin-4(3H)-one.

Gamal A El-Hiti¹, Keith Smith², Amany S Hegazy², Saud A Alanazi¹, Benson M Kariuki².

Abstract

In the title mol-ecule, C11H13N3O, the propyl group is almost perpendicular to the quinazolin-4(3H)-one mean plane, making a dihedral angle of 88.98 (9)°. In the crystal, mol-ecules related by an inversion centre are paired via π-π overlap, indicated by the short distances of 3.616 (5) and 3.619 (5) Å between the centroids of the aromatic rings of neighbouring mol-ecules. Inter-molecular N-H⋯N and N-H⋯O hydrogen bonds form R 6 (6)(30) rings and C(5) chains, respectively, generating a three-dimensional network. Weak C-H⋯O inter-actions are also observed.

Entities: CellLine Chemical Disease Species

Keywords: crystal structure; hydrogen bonding; quinazolin-4(3H)-one; π–π overlap

Year: 2015 PMID： 26396813 PMCID： PMC4571413 DOI： 10.1107/S2056989015013134

Source DB: PubMed Journal: Acta Crystallogr E Crystallogr Commun

Related literature

For biological applications of related compounds, see: Sasmal et al. (2012 ▸); Rohini et al. (2010 ▸); Chandregowda et al. (2009 ▸); Gupta et al. (2008 ▸); Alagarsamy et al. (2007 ▸). For the synthesis of substituted quinazolin-4(3H)-ones, see: Ma et al. (2013 ▸); Adib et al. (2012 ▸); Xu et al. (2012 ▸); Kumar et al. (2011 ▸). For modification of the quinazolin-4(3H)-one ring system via lithiation, see: Smith et al. (2004 ▸, 1996 ▸, 1995 ▸). For the crystal structures for related compounds, see: El-Hiti et al. (2014 ▸); Yang et al. (2009 ▸); Coogan et al. (1999 ▸).

Experimental

Crystal data

C11H13N3O M = 203.24 Trigonal, a = 24.1525 (5) Å c = 9.6500 (2) Å V = 4875.1 (2) Å3 Z = 18 Cu Kα radiation μ = 0.67 mm−1 T = 296 K 0.34 × 0.25 × 0.19 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.975, T max = 0.984 3734 measured reflections 2136 independent reflections 1913 reflections with I > 2σ(I) R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.120 S = 1.06 2136 reflections 146 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.17 e Å−3 Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and CHEMDRAW Ultra (Cambridge Soft, 2001 ▸). Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015013134/cv5493sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013134/cv5493Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015013134/cv5493Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015013134/cv5493fig1.tif View of (I) showing the atom labels and 50% probability displacement ellipsoids. Click here for additional data file. c . DOI: 10.1107/S2056989015013134/cv5493fig2.tif Crystal packing viewed along the c axis. CCDC reference: 1411448 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₁H₁₃N₃O	D_x = 1.246 Mg m⁻³
M_r = 203.24	Cu Kα radiation, λ = 1.54184 Å
Trigonal, R3:H	Cell parameters from 2040 reflections
a = 24.1525 (5) Å	θ = 5.0–74.1°
c = 9.6500 (2) Å	µ = 0.67 mm⁻¹
V = 4875.1 (2) Å³	T = 296 K
Z = 18	Block, colourless
F(000) = 1944	0.34 × 0.25 × 0.19 mm

Agilent SuperNova Dual Source diffractometer with an Atlas detector	1913 reflections with I > 2σ(I)
ω scans	R_int = 0.013
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	θ_max = 74.1°, θ_min = 3.7°
T_min = 0.975, T_max = 0.984	h = −21→30
3734 measured reflections	k = −26→18
2136 independent reflections	l = −11→10

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0637P)² + 1.4157P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.120	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.17 e Å⁻³
2136 reflections	Δρ_min = −0.15 e Å⁻³
146 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00114 (10)

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.

	x	y	z	U_iso*/U_eq
C1	0.23343 (6)	0.11120 (6)	0.00970 (12)	0.0453 (3)
C2	0.28221 (6)	0.06090 (5)	0.14259 (13)	0.0457 (3)
C3	0.27352 (5)	0.09197 (5)	0.26270 (12)	0.0440 (3)
C4	0.24674 (6)	0.13113 (6)	0.24439 (12)	0.0450 (3)
C5	0.29168 (6)	0.08293 (7)	0.39466 (14)	0.0535 (3)
H5	0.3089	0.0563	0.4064	0.064*
C6	0.28403 (7)	0.11345 (8)	0.50654 (14)	0.0618 (4)
H6	0.2958	0.1074	0.5946	0.074*
C7	0.25865 (8)	0.15367 (8)	0.48822 (14)	0.0630 (4)
H7	0.2544	0.1749	0.5643	0.076*
C8	0.23997 (7)	0.16241 (7)	0.36013 (14)	0.0567 (3)
H8	0.2228	0.1891	0.3498	0.068*
C9	0.20961 (7)	0.11882 (6)	−0.12831 (14)	0.0546 (3)
H9A	0.2357	0.1157	−0.2009	0.066*
H9B	0.2141	0.1610	−0.1337	0.066*
C10	0.13977 (8)	0.06846 (8)	−0.15299 (18)	0.0697 (4)
H10A	0.1359	0.0265	−0.1554	0.084*
H10B	0.1141	0.0691	−0.0763	0.084*
C11	0.11417 (10)	0.07946 (12)	−0.2869 (2)	0.0996 (7)
H11A	0.1222	0.1226	−0.2894	0.149*
H11B	0.0690	0.0503	−0.2924	0.149*
H11C	0.1351	0.0724	−0.3639	0.149*
N1	0.25905 (5)	0.07168 (5)	0.01918 (10)	0.0447 (3)
N2	0.22710 (5)	0.14035 (5)	0.11608 (11)	0.0486 (3)
N3	0.26483 (7)	0.04247 (6)	−0.10370 (12)	0.0550 (3)
O1	0.30729 (5)	0.02780 (5)	0.14300 (11)	0.0625 (3)
H3A	0.2287 (9)	0.0033 (10)	−0.1045 (18)	0.069 (5)*
H3B	0.2972 (10)	0.0370 (9)	−0.087 (2)	0.069 (5)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0447 (6)	0.0405 (6)	0.0464 (6)	0.0179 (5)	−0.0012 (5)	0.0016 (4)
C2	0.0425 (6)	0.0391 (5)	0.0518 (7)	0.0177 (5)	−0.0073 (5)	−0.0046 (5)
C3	0.0400 (6)	0.0401 (6)	0.0462 (6)	0.0158 (5)	−0.0028 (4)	−0.0002 (4)
C4	0.0441 (6)	0.0438 (6)	0.0439 (6)	0.0196 (5)	0.0021 (4)	0.0025 (4)
C5	0.0514 (7)	0.0554 (7)	0.0518 (7)	0.0253 (6)	−0.0067 (5)	0.0018 (5)
C6	0.0650 (8)	0.0724 (9)	0.0432 (7)	0.0307 (7)	−0.0043 (6)	0.0016 (6)
C7	0.0736 (9)	0.0695 (9)	0.0450 (7)	0.0350 (7)	0.0067 (6)	−0.0039 (6)
C8	0.0653 (8)	0.0603 (8)	0.0504 (7)	0.0358 (7)	0.0057 (6)	−0.0003 (6)
C9	0.0631 (8)	0.0512 (7)	0.0486 (7)	0.0279 (6)	−0.0060 (5)	0.0022 (5)
C10	0.0616 (9)	0.0732 (10)	0.0692 (9)	0.0300 (8)	−0.0086 (7)	0.0004 (7)
C11	0.0780 (12)	0.1036 (15)	0.0986 (15)	0.0315 (11)	−0.0333 (11)	0.0058 (12)
N1	0.0467 (5)	0.0401 (5)	0.0434 (5)	0.0189 (4)	−0.0036 (4)	−0.0052 (4)
N2	0.0546 (6)	0.0488 (6)	0.0462 (6)	0.0287 (5)	0.0001 (4)	0.0023 (4)
N3	0.0630 (7)	0.0499 (6)	0.0494 (6)	0.0263 (6)	−0.0042 (5)	−0.0120 (4)
O1	0.0729 (6)	0.0611 (6)	0.0683 (6)	0.0446 (5)	−0.0198 (5)	−0.0166 (4)

C1—N2	1.2963 (16)	C7—H7	0.9300
C1—N1	1.3760 (16)	C8—H8	0.9300
C1—C9	1.4981 (17)	C9—C10	1.526 (2)
C2—O1	1.2209 (15)	C9—H9A	0.9700
C2—N1	1.3945 (16)	C9—H9B	0.9700
C2—C3	1.4520 (17)	C10—C11	1.512 (2)
C3—C4	1.3984 (18)	C10—H10A	0.9700
C3—C5	1.3991 (18)	C10—H10B	0.9700
C4—N2	1.3832 (16)	C11—H11A	0.9600
C4—C8	1.4032 (18)	C11—H11B	0.9600
C5—C6	1.371 (2)	C11—H11C	0.9600
C5—H5	0.9300	N1—N3	1.4219 (14)
C6—C7	1.395 (2)	N3—H3A	0.91 (2)
C6—H6	0.9300	N3—H3B	0.87 (2)
C7—C8	1.368 (2)

N2—C1—N1	122.69 (11)	C1—C9—H9A	109.1
N2—C1—C9	118.73 (11)	C10—C9—H9A	109.1
N1—C1—C9	118.53 (11)	C1—C9—H9B	109.1
O1—C2—N1	120.11 (11)	C10—C9—H9B	109.1
O1—C2—C3	125.67 (12)	H9A—C9—H9B	107.9
N1—C2—C3	114.21 (10)	C11—C10—C9	112.30 (15)
C4—C3—C5	120.51 (12)	C11—C10—H10A	109.1
C4—C3—C2	118.94 (11)	C9—C10—H10A	109.1
C5—C3—C2	120.55 (11)	C11—C10—H10B	109.1
N2—C4—C3	122.27 (11)	C9—C10—H10B	109.1
N2—C4—C8	118.95 (12)	H10A—C10—H10B	107.9
C3—C4—C8	118.78 (12)	C10—C11—H11A	109.5
C6—C5—C3	119.73 (13)	C10—C11—H11B	109.5
C6—C5—H5	120.1	H11A—C11—H11B	109.5
C3—C5—H5	120.1	C10—C11—H11C	109.5
C5—C6—C7	119.93 (13)	H11A—C11—H11C	109.5
C5—C6—H6	120.0	H11B—C11—H11C	109.5
C7—C6—H6	120.0	C1—N1—C2	123.22 (10)
C8—C7—C6	121.04 (13)	C1—N1—N3	118.60 (10)
C8—C7—H7	119.5	C2—N1—N3	118.13 (10)
C6—C7—H7	119.5	C1—N2—C4	118.58 (11)
C7—C8—C4	119.99 (13)	N1—N3—H3A	104.0 (11)
C7—C8—H8	120.0	N1—N3—H3B	103.8 (13)
C4—C8—H8	120.0	H3A—N3—H3B	108.1 (17)
C1—C9—C10	112.34 (12)

O1—C2—C3—C4	176.78 (12)	N2—C1—C9—C10	−89.31 (15)
N1—C2—C3—C4	−3.10 (16)	N1—C1—C9—C10	88.39 (15)
O1—C2—C3—C5	−3.2 (2)	C1—C9—C10—C11	175.23 (16)
N1—C2—C3—C5	176.95 (11)	N2—C1—N1—C2	−1.99 (18)
C5—C3—C4—N2	−178.79 (11)	C9—C1—N1—C2	−179.59 (11)
C2—C3—C4—N2	1.26 (17)	N2—C1—N1—N3	−179.17 (11)
C5—C3—C4—C8	1.61 (18)	C9—C1—N1—N3	3.23 (16)
C2—C3—C4—C8	−178.34 (11)	O1—C2—N1—C1	−176.35 (11)
C4—C3—C5—C6	−0.98 (19)	C3—C2—N1—C1	3.54 (16)
C2—C3—C5—C6	178.97 (12)	O1—C2—N1—N3	0.84 (17)
C3—C5—C6—C7	−0.4 (2)	C3—C2—N1—N3	−179.27 (10)
C5—C6—C7—C8	1.2 (2)	N1—C1—N2—C4	−0.22 (18)
C6—C7—C8—C4	−0.6 (2)	C9—C1—N2—C4	177.38 (11)
N2—C4—C8—C7	179.55 (13)	C3—C4—N2—C1	0.51 (18)
C3—C4—C8—C7	−0.8 (2)	C8—C4—N2—C1	−179.89 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2ⁱ	0.91 (2)	2.16 (2)	3.0677 (17)	176.1 (16)
N3—H3B···O1ⁱⁱ	0.87 (2)	2.51 (2)	3.0599 (16)	122.0 (15)
C5—H5···O1ⁱⁱⁱ	0.93	2.44	3.3163 (16)	157

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N3H3AN2ⁱ	0.91(2)	2.16(2)	3.0677(17)	176.1(16)
N3H3BO1ⁱⁱ	0.87(2)	2.51(2)	3.0599(16)	122.0(15)
C5H5O1ⁱⁱⁱ	0.93	2.44	3.3163(16)	157

Symmetry codes: (i) ; (ii) ; (iii) .

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4. Design, synthesis and potential 6 Hz psychomotor seizure test activity of some novel 2-(substituted)-3-{[substituted]amino}quinazolin-4(3H)-one.

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5. Antimicrobial study of newly synthesized 6-substituted indolo[1,2-c]quinazolines.

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Authors: V Alagarsamy; V Raja Solomon; K Dhanabal
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