2-Ethyl-3-[(R)-2-phenyl­butanamido]­quinazolin-4(3H)-one monohydrate

El-Hiti, G.A.; Smith, K.; Hegazy, A.S.; Jones, D.H.; Kariuki, B.M.

doi:10.1107/S1600536814005996

organic compounds

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Volume 70| Part 4| April 2014| Page o467

doi:10.1107/S1600536814005996

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2-Ethyl-3-[(R)-2-phenylbutanamido]quinazolin-4(3H)-one monohydrate

Gamal A. El-Hiti,^a ^* Keith Smith,^b Amany S. Hegazy,^b D. Heulyn Jones ^b and Benson M. Kariuki ^b ^*

^aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, and ^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales
^*Correspondence e-mail: gelhiti@ksu.edu.sa, kariukib@cardiff.ac.uk

(Received 10 March 2014; accepted 18 March 2014; online 22 March 2014)

In the title compound, C₂₀H₂₁N₃O₂·H₂O (EQR·H₂O), the quinazoline ring system forms dihedral angles of 53.1 (1) and 85.6 (1)° with the phenyl ring and the amide link, respectively. In the crystal, O—H⋯O hydrogen bonds link two EQR and two water molecules into a centrosymmetric R₄⁴(18) ring motif. N—H⋯O hydrogen bonds further link these hydrogen-bonded fragments into columns extending in [010].

CCDC reference: 992297

Related literature

For convenient routes towards modifying 3H-quinazolin-4-one derivatives, see: Smith et al. (1995 , 1996a ,b , 2004 ). For the crystal structures of related compounds, see: Yang et al. (2009 ); Srinivasan et al. (2011 ).

Experimental

Crystal data

C₂₀H₂₁N₃O₂·H₂O
M_r = 353.41
Monoclinic, P 2₁ /n
a = 14.5354 (2) Å
b = 7.3529 (1) Å
c = 18.1945 (3) Å
β = 98.591 (1)°
V = 1922.76 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.68 mm⁻¹
T = 296 K
0.41 × 0.21 × 0.08 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014 ) T_min = 0.723, T_max = 1.000
13383 measured reflections
3796 independent reflections
3341 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.116
S = 1.05
3796 reflections
246 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3	0.86	1.92	2.7431 (15)	159
O3—H3A⋯O2ⁱ	0.92 (3)	1.89 (3)	2.7806 (15)	164 (2)
O3—H3B⋯O1ⁱⁱ	0.91 (3)	1.92 (3)	2.8154 (17)	169 (2)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z.

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, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (CambridgeSoft, 2001 ).

Supporting information

CCDC reference: 992297

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814005996/cv5446sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814005996/cv5446Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814005996/cv5446Isup3.cml

checkCIF report

Comment top

In a continuation of our research focused on new synthetic routes towards novel substituted 3H-quinazolin-4-one derivatives (Smith et al., 1995, 1996a,b, 2004) we have synthesized 2-ethyl-3-((R)-2-phenylbutanoylamino)-3H-quinazolin-4-one (EQR) in a high yield. Herewith we present the crystal structure of its monohydrate.

In the title compound, EQR.H₂O (Fig. 1), all bond lengths and angles are normal and correspond well to those observed in the related structures (Smith et al., 2004; Yang et al., 2009; Srinivasan et al., 2011). The quinazoline ring system forms a dihedral angle of 53.1 (1)° with the phenyl ring and an angle of 85.6 (1)° with the amide link. A pair of EQR molecules accepts O–H···O hydrogen bonds from two water molecules to form a R⁴₄(18) ring motif. These rings are linked by N–H···O bonds to form columns parallel to the b-axis (Fig. 2).

Related literature top

For convenient routes towards modifying 3H-quinazolin-4-one derivatives, see: Smith et al. (1995, 1996a,b, 2004). For the crystal structures of related compounds, see: Yang et al. (2009); Srinivasan et al. (2011).

Experimental top

To a stirred mixture of 3-amino-2-ethyl-3H-quinazolin-4-one (1.89 g, 10.0 mmol) and Et₃N (3 ml) in anhydrous toluene (20 ml), was added a solution of 2-phenylbutanoyl chloride (0.91 g, 5.0 mmol) in anhydrous toluene (5 ml). The mixture was heated under reflux for 30 min, allowed to cool, washed with saturated aqueous NaHCO₃ (2 x 10 ml) and H₂O (2 x 15 ml), dried (MgSO₄), and evaporated under reduced pressure. The residue obtained was purified by column chromatography on silica gel (Et₂O–hexane, 1:4) followed by recrystallization from ethyl acetate to give 2-ethyl-3-(2-phenylbutanoylamino)-3H-quinazolin-4-one (1.36 g, 4.05 mmol; 81% based on acid chloride) as colourless crystals, m.p. 101–103 °C. The title compound (I) appears from its NMR spectra as a mixture of two diastereoisomers in unequal proportions (Ia:Ib = ca. 4:6), due to restricted rotation around the N–N axis (Smith et al., 2004), but the X-ray crystallography showed a single type of crystal containing just one diastereoisomer but with both enantiomers in equal proportions (the structure displayed shows the structure as 2-ethyl-3-((R)-2-phenylbutanoylamino)-3H-quinazolin-4-one hydrate). The ¹H NMR spectrum also showed diastereotopism for the CH₂ protons of the ethyl groups, but was temperature dependent and showed a single set of signals at 150 °C (Smith et al., 2004). EI–MS: m/z (%) = 335 (M⁺, 5), 216 (40), 189 (17), 173 (12), 119 (65), 91 (100). HRMS (EI): Calculated for C₂₀H₂₁N₃O₂ [M]: 335.1634; found, 335.1634. NMR assignments have been made on the basis of expected chemical shifts and coupling patterns and have not been rigorously confirmed.

¹H NMR (500 MHz, DMSO-d₆, δ, p.p.m.) 8.15 (d, J = 8 Hz, 0.6 H, H-5 of Ib), 8.06 (d, J = 8 Hz, 0.4 H, H-5 of Ia), 7.87–7.82 (m, 1 H, H-7 of Ia and Ib), 7.68 (d, J = 8 Hz, 0.4 H, H-8 of Ia), 7.65 (d, J = 8 Hz, 0.6 H, H-8 of Ib), 7.57–5.48 (m, 1 H, H-6 of Ia and Ib), 7.45–7.35 (m, 4 H, H-2 and H-3 of Ph of Ia and Ib), 7.32–7.27 (m, 1 H, H-4 of Ph of Ia and Ib), 3.75–3.67 (m, 1 H, CH of Ia and Ib), 2.76 (dq, J = 15, 7.5 Hz, 0.4 H, ArCH_aH_b of Ia), 2.63 (dq, J = 15, 7.5 Hz, 0.4 H, ArCH_aH_b of Ia), 2.30 (dq, J = 15, 7.5 Hz, 0.6 Hz, ArCH_aH_b of Ib), 2.20 (dq, J = 15, 7.5 Hz, 0.6 H, ArCH_aH_b of Ib), 2.18–2.04 (m, 1 H, CHCH_aH_b of Ia and Ib), 1.86–1.71 (m, 1 H, CHCH_aH_b of Ia and Ib), 1.25 (app. t, J = 7.5 Hz, 1.2 H, CH₃CH₂Ar of Ia), 0.99 (app. t, J = 7.5 Hz, 1.8 H, CH₃CH₂Ar of Ib), 0.96–0.90 (m, 3 H, CH₃CH₂CH of Ia and Ib). ¹³C NMR (125 MHz, DMSO-d₆, δ, p.p.m.) 173.0 (s, C=O of Ia), 172.9 (s, C=O of Ib), 159.7 (s, C-4 of Ib), 159.6 (s, C-4 of Ia), 159.5 (s, C-2 of Ib), 159.3 (s, C-2 of Ia), 147.1 (s, C-8a of Ib), 147.0 (s, C-8a of Ia), 139.9 (s, C-1 of Ph of Ib), 139.6 (s, C-1 of Ph of Ia), 135.4 (d, C-7 of Ib), 135.3 (d, C-7 of Ia), 128.9 (d, C-3/C-5 of Ph of Ib), 128.7 (d, C-3/C-5 of Ph of Ia), 128.5 (d, C-2/C-6 of Ph od Ia), 128.1 (d, C-2/C-6 of Ph of Ib), 127.6 (d, three overlapping signals, C-6 of Ia and Ib and C-8 of Ib), 127.4 (d, C-8 of Ia), 127.2 (d, C-5 of Ib), 127.1 (d, C-5 of Ia), 126.9 (d, C-4 of Ph), 126.8 (d, C-4 of Ph), 121.1 (s, two overlapping signals, C-4a of Ia and Ib), 51.9 (d, CH of Ia), 51.8 (d, CH of Ib), 27.0 (t, CH₂CH of Ia), 26.9 (t, CH₂CH of Ib), 26.6 (t, CH₂Ar of Ib), 25.9 (t, CH₂Ar of Ia), 12.6 (q, CH₃CH₂CH of Ia), 12.5 (q, CH₃CH₂CH of Ib), 11.0 (q, CH₃CH₂Ar of Ia), 10.8 (q, CH₃CH₂Ar of Ib).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (CambridgeSoft, 2001).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A portion of the crystal packing viewed along the a axis and showing the hydrogen bonds as dotted green lines. C-bound H atoms were omitted for clarity.

2-Ethyl-3-[(R)-2-phenylbutanamido]quinazolin-4(3H)-one monohydrate top

Crystal data top

C₂₀H₂₁N₃O₂·H₂O	F(000) = 752
M_r = 353.41	D_x = 1.221 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 14.5354 (2) Å	Cell parameters from 3341 reflections
b = 7.3529 (1) Å	θ = 3.6–67.7°
c = 18.1945 (3) Å	µ = 0.68 mm⁻¹
β = 98.591 (1)°	T = 296 K
V = 1922.76 (5) Å³	Plate, colourless
Z = 4	0.41 × 0.21 × 0.08 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3341 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	R_int = 0.017
ω scans	θ_max = 73.5°, θ_min = 3.6°
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	h = −16→17
T_min = 0.723, T_max = 1.000	k = −9→8
13383 measured reflections	l = −22→21
3796 independent reflections

Refinement top

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) + (0.0544P)² + 0.3851P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.116	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.29 e Å⁻³
3796 reflections	Δρ_min = −0.36 e Å⁻³
246 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0033 (3)

Crystal data top

C₂₀H₂₁N₃O₂·H₂O	V = 1922.76 (5) Å³
M_r = 353.41	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 14.5354 (2) Å	µ = 0.68 mm⁻¹
b = 7.3529 (1) Å	T = 296 K
c = 18.1945 (3) Å	0.41 × 0.21 × 0.08 mm
β = 98.591 (1)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3796 independent reflections
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	3341 reflections with I > 2σ(I)
T_min = 0.723, T_max = 1.000	R_int = 0.017
13383 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.29 e Å⁻³
3796 reflections	Δρ_min = −0.36 e Å⁻³
246 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro (Agilent, 2014): Numerical absorption correction based on Gaussian integration over a multifaceted crystal model. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

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

	x	y	z	U_iso*/U_eq
C1	0.71716 (9)	0.66803 (17)	0.06334 (7)	0.0466 (3)
C2	0.81747 (9)	0.69215 (18)	0.07879 (8)	0.0525 (3)
C3	0.85958 (9)	0.72040 (19)	0.15199 (9)	0.0557 (3)
C4	0.72196 (9)	0.69526 (17)	0.19860 (7)	0.0470 (3)
C5	0.87036 (12)	0.6905 (3)	0.02072 (11)	0.0732 (5)
H5	0.8418	0.6688	−0.0277	0.088*
C6	0.96387 (14)	0.7207 (3)	0.03496 (15)	0.0952 (7)
H6	0.9992	0.7205	−0.0037	0.114*
C7	1.00601 (13)	0.7517 (3)	0.10751 (16)	0.0979 (7)
H7	1.0697	0.7731	0.1168	0.117*
C8	0.95599 (11)	0.7514 (3)	0.16581 (13)	0.0796 (5)
H8	0.9857	0.7715	0.2140	0.096*
C9	0.52278 (8)	0.79347 (16)	0.10850 (7)	0.0410 (3)
C10	0.41982 (8)	0.74708 (17)	0.10069 (7)	0.0418 (3)
H10	0.4092	0.6357	0.0711	0.050*
C11	0.39529 (8)	0.70884 (18)	0.17738 (7)	0.0456 (3)
C12	0.34870 (10)	0.5513 (2)	0.19121 (8)	0.0593 (4)
H12	0.3334	0.4666	0.1534	0.071*
C13	0.32464 (13)	0.5187 (3)	0.26100 (10)	0.0781 (5)
H13	0.2928	0.4128	0.2695	0.094*
C14	0.34730 (15)	0.6408 (3)	0.31718 (10)	0.0835 (5)
H14	0.3308	0.6185	0.3638	0.100*
C15	0.39456 (14)	0.7967 (3)	0.30473 (9)	0.0769 (5)
H15	0.4110	0.8791	0.3432	0.092*
C16	0.41781 (11)	0.8314 (2)	0.23522 (8)	0.0600 (4)
H16	0.4490	0.9383	0.2271	0.072*
C17	0.66472 (11)	0.6937 (2)	0.26021 (8)	0.0611 (4)
H17A	0.6266	0.5848	0.2559	0.073*
H17B	0.6232	0.7977	0.2545	0.073*
C18	0.72124 (14)	0.6992 (3)	0.33713 (9)	0.0749 (5)
H18A	0.7599	0.5929	0.3445	0.112*
H18B	0.6800	0.7021	0.3737	0.112*
H18C	0.7597	0.8060	0.3419	0.112*
C19	0.35937 (9)	0.8981 (2)	0.06048 (7)	0.0512 (3)
H19A	0.3635	1.0057	0.0916	0.061*
H19B	0.3826	0.9292	0.0148	0.061*
C20	0.25831 (10)	0.8397 (2)	0.04242 (9)	0.0628 (4)
H20A	0.2540	0.7337	0.0113	0.094*
H20B	0.2224	0.9364	0.0169	0.094*
H20C	0.2346	0.8119	0.0876	0.094*
N1	0.81045 (8)	0.72053 (16)	0.21145 (7)	0.0557 (3)
N2	0.67465 (7)	0.66873 (14)	0.12675 (6)	0.0429 (2)
N3	0.57841 (7)	0.64529 (14)	0.11660 (6)	0.0446 (3)
H3	0.5547	0.5380	0.1155	0.054*
O1	0.67227 (7)	0.64818 (15)	0.00151 (5)	0.0613 (3)
O2	0.55448 (6)	0.94696 (12)	0.11169 (6)	0.0557 (3)
O3	0.50861 (9)	0.30699 (16)	0.07666 (10)	0.0873 (5)
H3A	0.5189 (19)	0.193 (4)	0.0963 (14)	0.124 (9)*
H3B	0.450 (2)	0.306 (4)	0.0514 (15)	0.123 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0444 (6)	0.0406 (6)	0.0543 (7)	0.0049 (5)	0.0061 (5)	0.0001 (5)
C2	0.0436 (7)	0.0456 (7)	0.0687 (8)	0.0041 (5)	0.0100 (6)	0.0023 (6)
C3	0.0412 (7)	0.0474 (7)	0.0766 (9)	0.0026 (5)	0.0032 (6)	0.0011 (6)
C4	0.0482 (7)	0.0384 (6)	0.0518 (7)	0.0015 (5)	−0.0008 (5)	0.0040 (5)
C5	0.0592 (9)	0.0781 (11)	0.0871 (12)	0.0042 (8)	0.0264 (8)	−0.0011 (9)
C6	0.0634 (11)	0.1038 (16)	0.1273 (19)	−0.0029 (10)	0.0433 (12)	−0.0105 (14)
C7	0.0429 (9)	0.1033 (15)	0.151 (2)	−0.0051 (9)	0.0268 (11)	−0.0150 (15)
C8	0.0432 (8)	0.0802 (12)	0.1115 (15)	−0.0009 (8)	−0.0010 (8)	−0.0100 (10)
C9	0.0421 (6)	0.0375 (6)	0.0439 (6)	0.0001 (5)	0.0077 (5)	0.0028 (5)
C10	0.0387 (6)	0.0418 (6)	0.0451 (6)	−0.0001 (5)	0.0069 (5)	0.0000 (5)
C11	0.0392 (6)	0.0504 (7)	0.0473 (6)	−0.0002 (5)	0.0070 (5)	0.0036 (5)
C12	0.0591 (8)	0.0608 (9)	0.0582 (8)	−0.0127 (7)	0.0088 (6)	0.0058 (7)
C13	0.0840 (12)	0.0812 (12)	0.0721 (10)	−0.0192 (9)	0.0212 (9)	0.0191 (9)
C14	0.1001 (14)	0.0986 (14)	0.0564 (9)	−0.0080 (11)	0.0265 (9)	0.0127 (9)
C15	0.0934 (13)	0.0861 (12)	0.0536 (9)	−0.0062 (10)	0.0185 (8)	−0.0089 (8)
C16	0.0655 (9)	0.0603 (9)	0.0561 (8)	−0.0090 (7)	0.0157 (7)	−0.0048 (6)
C17	0.0644 (9)	0.0651 (9)	0.0533 (8)	0.0004 (7)	0.0074 (6)	0.0071 (7)
C18	0.0978 (13)	0.0720 (11)	0.0522 (8)	−0.0035 (9)	0.0023 (8)	0.0017 (7)
C19	0.0465 (7)	0.0560 (8)	0.0516 (7)	0.0083 (6)	0.0096 (5)	0.0071 (6)
C20	0.0473 (7)	0.0793 (10)	0.0590 (8)	0.0111 (7)	−0.0012 (6)	−0.0030 (7)
N1	0.0464 (6)	0.0538 (7)	0.0627 (7)	0.0000 (5)	−0.0057 (5)	0.0015 (5)
N2	0.0356 (5)	0.0398 (5)	0.0521 (6)	0.0007 (4)	0.0025 (4)	0.0010 (4)
N3	0.0350 (5)	0.0363 (5)	0.0618 (6)	−0.0024 (4)	0.0046 (4)	0.0000 (4)
O1	0.0554 (6)	0.0734 (7)	0.0533 (6)	0.0040 (5)	0.0022 (4)	−0.0047 (5)
O2	0.0473 (5)	0.0367 (5)	0.0830 (7)	−0.0019 (4)	0.0092 (4)	0.0053 (4)
O3	0.0695 (8)	0.0397 (6)	0.1395 (13)	−0.0015 (5)	−0.0278 (8)	−0.0025 (6)

Geometric parameters (Å, º) top

C1—O1	1.2220 (16)	C12—C13	1.387 (2)
C1—N2	1.3879 (17)	C12—H12	0.9300
C1—C2	1.4539 (18)	C13—C14	1.364 (3)
C2—C3	1.396 (2)	C13—H13	0.9300
C2—C5	1.397 (2)	C14—C15	1.372 (3)
C3—N1	1.382 (2)	C14—H14	0.9300
C3—C8	1.405 (2)	C15—C16	1.381 (2)
C4—N1	1.2860 (17)	C15—H15	0.9300
C4—N2	1.3969 (16)	C16—H16	0.9300
C4—C17	1.493 (2)	C17—C18	1.514 (2)
C5—C6	1.363 (3)	C17—H17A	0.9700
C5—H5	0.9300	C17—H17B	0.9700
C6—C7	1.389 (3)	C18—H18A	0.9600
C6—H6	0.9300	C18—H18B	0.9600
C7—C8	1.373 (3)	C18—H18C	0.9600
C7—H7	0.9300	C19—C20	1.519 (2)
C8—H8	0.9300	C19—H19A	0.9700
C9—O2	1.2172 (15)	C19—H19B	0.9700
C9—N3	1.3516 (16)	C20—H20A	0.9600
C9—C10	1.5208 (16)	C20—H20B	0.9600
C10—C11	1.5171 (17)	C20—H20C	0.9600
C10—C19	1.5324 (17)	N2—N3	1.3941 (14)
C10—H10	0.9800	N3—H3	0.8600
C11—C12	1.3836 (19)	O3—H3A	0.92 (3)
C11—C16	1.387 (2)	O3—H3B	0.91 (3)

O1—C1—N2	121.53 (12)	C13—C14—C15	119.81 (16)
O1—C1—C2	125.08 (13)	C13—C14—H14	120.1
N2—C1—C2	113.39 (12)	C15—C14—H14	120.1
C3—C2—C5	120.71 (14)	C14—C15—C16	120.18 (17)
C3—C2—C1	119.13 (13)	C14—C15—H15	119.9
C5—C2—C1	120.14 (14)	C16—C15—H15	119.9
N1—C3—C2	122.86 (12)	C15—C16—C11	120.84 (15)
N1—C3—C8	118.55 (15)	C15—C16—H16	119.6
C2—C3—C8	118.58 (16)	C11—C16—H16	119.6
N1—C4—N2	121.97 (13)	C4—C17—C18	114.06 (14)
N1—C4—C17	121.28 (12)	C4—C17—H17A	108.7
N2—C4—C17	116.75 (11)	C18—C17—H17A	108.7
C6—C5—C2	120.05 (19)	C4—C17—H17B	108.7
C6—C5—H5	120.0	C18—C17—H17B	108.7
C2—C5—H5	120.0	H17A—C17—H17B	107.6
C5—C6—C7	119.54 (19)	C17—C18—H18A	109.5
C5—C6—H6	120.2	C17—C18—H18B	109.5
C7—C6—H6	120.2	H18A—C18—H18B	109.5
C8—C7—C6	121.67 (17)	C17—C18—H18C	109.5
C8—C7—H7	119.2	H18A—C18—H18C	109.5
C6—C7—H7	119.2	H18B—C18—H18C	109.5
C7—C8—C3	119.43 (19)	C20—C19—C10	111.44 (12)
C7—C8—H8	120.3	C20—C19—H19A	109.3
C3—C8—H8	120.3	C10—C19—H19A	109.3
O2—C9—N3	121.75 (11)	C20—C19—H19B	109.3
O2—C9—C10	124.94 (11)	C10—C19—H19B	109.3
N3—C9—C10	113.18 (10)	H19A—C19—H19B	108.0
C11—C10—C9	108.59 (10)	C19—C20—H20A	109.5
C11—C10—C19	112.12 (10)	C19—C20—H20B	109.5
C9—C10—C19	111.61 (10)	H20A—C20—H20B	109.5
C11—C10—H10	108.1	C19—C20—H20C	109.5
C9—C10—H10	108.1	H20A—C20—H20C	109.5
C19—C10—H10	108.1	H20B—C20—H20C	109.5
C12—C11—C16	118.18 (13)	C4—N1—C3	118.51 (12)
C12—C11—C10	120.74 (12)	C1—N2—N3	116.87 (10)
C16—C11—C10	121.08 (12)	C1—N2—C4	124.09 (11)
C11—C12—C13	120.56 (15)	N3—N2—C4	119.02 (10)
C11—C12—H12	119.7	C9—N3—N2	119.14 (10)
C13—C12—H12	119.7	C9—N3—H3	120.4
C14—C13—C12	120.43 (16)	N2—N3—H3	120.4
C14—C13—H13	119.8	H3A—O3—H3B	106 (2)
C12—C13—H13	119.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3	0.86	1.92	2.7431 (15)	159
O3—H3A···O2ⁱ	0.92 (3)	1.89 (3)	2.7806 (15)	164 (2)
O3—H3B···O1ⁱⁱ	0.91 (3)	1.92 (3)	2.8154 (17)	169 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3	0.86	1.92	2.7431 (15)	159.4
O3—H3A···O2ⁱ	0.92 (3)	1.89 (3)	2.7806 (15)	164 (2)
O3—H3B···O1ⁱⁱ	0.91 (3)	1.92 (3)	2.8154 (17)	169 (2)

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

Acknowledgements

The authors thank the College of Applied Medical Sciences Research Center and the Deanship of Scientific Research at King Saud University for funding this research.

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