1-(3-Hy­droxy­prop­yl)-3-phenyl­quinoxalin-2(1H)-one

Abad, N.; Ramli, Y.; Lahmidi, S.; El Hafi, M.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314618016334

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 11| November 2018| x181633

https://doi.org/10.1107/S2414314618016334

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1-(3-Hydroxypropyl)-3-phenylquinoxalin-2(1H)-one

Nadeem Abad,^a Youssef Ramli,^b Sanae Lahmidi,^a ^* Mohamed El Hafi,^a El Mokhtar Essassi ^a and Joel T. Mague ^c

^aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche Des Sciences des Médicaments, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^bLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University Rabat, Morocco, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: asb.sanae@gmail.com

Edited by A. J. Lough, University of Toronto, Canada (Received 12 October 2018; accepted 17 November 2018; online 30 November 2018)

In the title molecule, C₁₇H₁₆N₂O₂, the quinoxaline portion is slightly folded about the N⋯N axis with an angle of 4.27 (4)°. In the crystal, O—H⋯O and weak C—H⋯O hydrogen bonds link molecules along the b-axis direction. In addition, two sets of weak C—H⋯π(ring) interactions form a two-dimensional `step' motif parallel to the bc plane.

Keywords: crystal structure; dihydroquinoxaline; hydrogen bond; C—H⋯π(ring).

CCDC reference: 1879633

Structure description

Quinoxalines and their derivatives, especially the quinoxalinones, are of great importance in medicinal chemistry (Ramli & Essassi, 2015 ). As a continuation of our work on the synthesis of quinoxalin-2-one derivatives in order to evaluate their pharmacological activities (Ramli et al., 2010a ,b, 2011 , 2013 ; Caleb et al., 2016 ; Missioui et al., 2017 ) we report herein the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The dihydroquinoxaline fragment shows a slight fold of 4.27 (4)° about the N1⋯N2 axis and the C9–C14 phenyl ring is inclined at 44.89 (3)° to the mean plane of the N1/N2/C1–C6 fragment. In the crystal, O—H⋯O and weak C—H⋯O hydrogen bonds form ribbons two molecules wide extending along the b-axis direction. Each half of the ribbon is reinforced by C3—H3⋯Cg1ⁱⁱ interactions (Table 1 and Fig. 2). The ribbons are connected into a `step' motif running parallel to the bc plane by C10—H10⋯Cg2ⁱⁱⁱ interactions (Table 1 and Figs. 2–4 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C14 and C1–C6 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1ⁱ	0.949 (15)	1.888 (15)	2.8345 (10)	174.4 (14)
C15—H15A⋯O2ⁱⁱ	0.969 (11)	2.582 (12)	3.3425 (13)	135.5 (9)
C3—H3⋯Cg1ⁱⁱⁱ	0.953 (12)	2.734 (12)	3.4708 (12)	134.8 (9)
C10—H10⋯Cg2^iv	1.003 (12)	2.916 (13)	3.5859 (12)	124.9 (9)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x, y-1, z; (iv) -x+1, -y+1, -z+1.

Figure 1
The molecular structure of the title molecule with the labelling scheme and 50% probability ellipsoids.

Figure 2
Part of the crystal structure viewed along the a-axis direction. The O—H⋯O and C—H⋯O hydrogen bonds are shown, respectively, by red and black dashed lines. C—H⋯π(ring) interactions are shown by green dashed lines.

Figure 3
Part of the crystal structure viewed along the c-axis direction showing C—H⋯π(ring) interactions as green dashed lines. Hydrogen bonds are as depicted as in Fig. 2

Figure 4
A view of portions of two chains viewed along the b-axis direction showing their association through C—H⋯π(ring) interactions. These and the hydrogen bonds are depicted as in Fig. 2

Synthesis and crystallization

A solution of 1-(3-bromopropyl)-3-phenylquinoxalin-2(1H)-one (1 g, 2.9 mmol) methanol/water (20/5 ml) was stirred under reflex for 12 h. After completion of the reaction (monitored by TLC), the solution was concentrated and the residue was purified by column chromatography on silica gel by using a mixture (hexane/ethyl acetate 9/1). The solid product was purified by recrystallization from ethanol solution to afford colourless crystals in 20% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₂
M_r	280.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	8.1914 (14), 9.5151 (16), 17.781 (3)
β (°)	94.880 (2)
V (Å³)	1380.9 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.30 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.90, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	26403, 3863, 3134
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.696

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.135, 1.10
No. of reflections	3863
No. of parameters	254
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.25
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2018/1 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1879633

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618016334/lh4040sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618016334/lh4040Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618016334/lh4040Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314618016334/lh4040Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1-(3-Hydroxypropyl)-3-phenylquinoxalin-2(1H)-one top

Crystal data top

C₁₇H₁₆N₂O₂	F(000) = 592
M_r = 280.32	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.1914 (14) Å	Cell parameters from 9996 reflections
b = 9.5151 (16) Å	θ = 2.3–29.5°
c = 17.781 (3) Å	µ = 0.09 mm⁻¹
β = 94.880 (2)°	T = 120 K
V = 1380.9 (4) Å³	Block, colourless
Z = 4	0.36 × 0.30 × 0.24 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3863 independent reflections
Radiation source: fine-focus sealed tube	3134 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.7°, θ_min = 2.3°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→13
T_min = 0.90, T_max = 0.98	l = −24→24
26403 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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.135	All H-atom parameters refined
S = 1.10	w = 1/[σ²(F_o²) + (0.0966P)²] where P = (F_o² + 2F_c²)/3
3863 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 10 sec/frame.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.27209 (9)	0.74659 (7)	0.56746 (4)	0.02520 (19)
O2	0.22106 (10)	0.33666 (7)	0.78036 (4)	0.0312 (2)
H2A	0.2164 (19)	0.3088 (16)	0.8314 (8)	0.048 (4)*
N1	0.20531 (9)	0.51397 (8)	0.56730 (4)	0.01714 (18)
N2	0.23410 (10)	0.50846 (8)	0.41202 (4)	0.01962 (19)
C1	0.19860 (11)	0.38735 (9)	0.45045 (5)	0.0185 (2)
C2	0.17979 (12)	0.26102 (9)	0.40970 (6)	0.0222 (2)
H2	0.1884 (17)	0.2662 (13)	0.3542 (8)	0.032 (3)*
C3	0.15117 (12)	0.13665 (10)	0.44606 (6)	0.0229 (2)
H3	0.1392 (14)	0.0507 (13)	0.4187 (6)	0.024 (3)*
C4	0.13883 (12)	0.13696 (10)	0.52385 (6)	0.0220 (2)
H4	0.1204 (15)	0.0500 (13)	0.5494 (7)	0.032 (3)*
C5	0.15550 (11)	0.25972 (9)	0.56534 (5)	0.0203 (2)
H5	0.1496 (15)	0.2574 (11)	0.6206 (8)	0.027 (3)*
C6	0.18532 (10)	0.38650 (9)	0.52882 (5)	0.01701 (19)
C7	0.24818 (11)	0.63536 (9)	0.53240 (5)	0.01806 (19)
C8	0.25998 (11)	0.62434 (9)	0.44965 (5)	0.01757 (19)
C9	0.30450 (11)	0.75076 (9)	0.40701 (5)	0.0181 (2)
C10	0.43131 (12)	0.83965 (10)	0.43404 (5)	0.0200 (2)
H10	0.4888 (16)	0.8204 (13)	0.4851 (7)	0.029 (3)*
C11	0.47873 (12)	0.95075 (10)	0.39000 (6)	0.0232 (2)
H11	0.5651 (15)	1.0131 (11)	0.4081 (6)	0.022 (3)*
C12	0.39868 (12)	0.97456 (10)	0.31921 (5)	0.0238 (2)
H12	0.4319 (17)	1.0523 (15)	0.2884 (8)	0.047 (4)*
C13	0.27064 (12)	0.88795 (10)	0.29237 (5)	0.0231 (2)
H13	0.2131 (16)	0.9078 (14)	0.2422 (8)	0.036 (3)*
C14	0.22437 (12)	0.77595 (10)	0.33558 (5)	0.0214 (2)
H14	0.1360 (15)	0.7173 (12)	0.3173 (7)	0.023 (3)*
C15	0.18946 (11)	0.51763 (10)	0.64903 (5)	0.0191 (2)
H15A	0.1498 (14)	0.6104 (12)	0.6607 (6)	0.024 (3)*
H15B	0.1017 (13)	0.4501 (11)	0.6590 (6)	0.017 (3)*
C16	0.35032 (12)	0.47987 (12)	0.69358 (5)	0.0256 (2)
H16A	0.4287 (15)	0.5601 (13)	0.6897 (7)	0.031 (3)*
H16B	0.4001 (16)	0.3962 (14)	0.6743 (7)	0.032 (3)*
C17	0.32545 (15)	0.45535 (12)	0.77586 (6)	0.0302 (2)
H17A	0.2795 (15)	0.5397 (13)	0.8020 (7)	0.033 (3)*
H17B	0.4311 (18)	0.4404 (14)	0.8036 (8)	0.042 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0405 (4)	0.0198 (3)	0.0159 (4)	−0.0061 (3)	0.0058 (3)	−0.0034 (2)
O2	0.0500 (5)	0.0257 (4)	0.0187 (4)	0.0036 (3)	0.0068 (3)	0.0059 (3)
N1	0.0217 (4)	0.0188 (4)	0.0110 (4)	−0.0012 (3)	0.0014 (3)	0.0001 (3)
N2	0.0249 (4)	0.0194 (4)	0.0147 (4)	−0.0030 (3)	0.0021 (3)	−0.0011 (3)
C1	0.0221 (4)	0.0185 (4)	0.0148 (4)	−0.0021 (3)	0.0014 (3)	0.0001 (3)
C2	0.0284 (5)	0.0220 (5)	0.0165 (4)	−0.0037 (4)	0.0031 (4)	−0.0030 (3)
C3	0.0255 (5)	0.0196 (4)	0.0235 (5)	−0.0037 (4)	0.0020 (4)	−0.0026 (3)
C4	0.0225 (4)	0.0201 (4)	0.0232 (5)	−0.0040 (3)	0.0009 (4)	0.0022 (3)
C5	0.0223 (4)	0.0218 (5)	0.0166 (4)	−0.0028 (3)	0.0014 (3)	0.0020 (3)
C6	0.0176 (4)	0.0185 (4)	0.0149 (4)	−0.0010 (3)	0.0006 (3)	−0.0006 (3)
C7	0.0218 (4)	0.0190 (4)	0.0135 (4)	−0.0009 (3)	0.0020 (3)	−0.0006 (3)
C8	0.0213 (4)	0.0190 (4)	0.0125 (4)	−0.0011 (3)	0.0020 (3)	0.0007 (3)
C9	0.0234 (4)	0.0174 (4)	0.0139 (4)	0.0000 (3)	0.0044 (3)	0.0005 (3)
C10	0.0232 (4)	0.0204 (4)	0.0164 (4)	0.0001 (3)	0.0013 (3)	0.0011 (3)
C11	0.0256 (5)	0.0215 (5)	0.0226 (5)	−0.0031 (4)	0.0036 (4)	0.0016 (4)
C12	0.0301 (5)	0.0216 (4)	0.0205 (5)	0.0010 (4)	0.0071 (4)	0.0058 (3)
C13	0.0290 (5)	0.0269 (5)	0.0136 (4)	0.0036 (4)	0.0026 (3)	0.0028 (3)
C14	0.0255 (5)	0.0238 (4)	0.0150 (4)	−0.0017 (4)	0.0021 (3)	−0.0004 (3)
C15	0.0245 (4)	0.0222 (4)	0.0106 (4)	−0.0016 (4)	0.0024 (3)	0.0002 (3)
C16	0.0249 (5)	0.0358 (5)	0.0157 (4)	−0.0029 (4)	−0.0011 (4)	0.0024 (4)
C17	0.0384 (6)	0.0358 (6)	0.0156 (5)	−0.0003 (5)	−0.0028 (4)	0.0019 (4)

Geometric parameters (Å, º) top

O1—C7	1.2354 (11)	C9—C10	1.3930 (13)
O2—C17	1.4229 (14)	C9—C14	1.3998 (13)
O2—H2A	0.949 (15)	C10—C11	1.3904 (12)
N1—C7	1.3710 (11)	C10—H10	1.003 (12)
N1—C6	1.3954 (11)	C11—C12	1.3876 (14)
N1—C15	1.4704 (11)	C11—H11	0.958 (12)
N2—C8	1.2977 (11)	C12—C13	1.3862 (14)
N2—C1	1.3832 (11)	C12—H12	0.973 (15)
C1—C2	1.4051 (12)	C13—C14	1.3854 (13)
C1—C6	1.4071 (12)	C13—H13	0.991 (14)
C2—C3	1.3781 (13)	C14—H14	0.950 (12)
C2—H2	0.996 (13)	C15—C16	1.5216 (14)
C3—C4	1.3954 (14)	C15—H15A	0.969 (11)
C3—H3	0.953 (12)	C15—H15B	0.991 (10)
C4—C5	1.3822 (13)	C16—C17	1.5123 (14)
C4—H4	0.962 (13)	C16—H16A	1.003 (13)
C5—C6	1.4012 (12)	C16—H16B	0.970 (13)
C5—H5	0.988 (13)	C17—H17A	1.016 (12)
C7—C8	1.4865 (12)	C17—H17B	0.969 (15)
C8—C9	1.4838 (12)

C17—O2—H2A	110.4 (9)	C11—C10—H10	121.1 (7)
C7—N1—C6	122.30 (7)	C9—C10—H10	118.7 (7)
C7—N1—C15	118.36 (7)	C12—C11—C10	120.13 (9)
C6—N1—C15	119.25 (7)	C12—C11—H11	118.8 (7)
C8—N2—C1	119.03 (8)	C10—C11—H11	121.0 (7)
N2—C1—C2	118.46 (8)	C13—C12—C11	120.04 (9)
N2—C1—C6	122.09 (8)	C13—C12—H12	119.8 (8)
C2—C1—C6	119.43 (8)	C11—C12—H12	120.2 (8)
C3—C2—C1	120.55 (9)	C14—C13—C12	120.06 (9)
C3—C2—H2	122.4 (7)	C14—C13—H13	120.9 (8)
C1—C2—H2	117.0 (7)	C12—C13—H13	119.0 (8)
C2—C3—C4	119.52 (9)	C13—C14—C9	120.38 (9)
C2—C3—H3	120.8 (7)	C13—C14—H14	120.0 (7)
C4—C3—H3	119.7 (7)	C9—C14—H14	119.6 (7)
C5—C4—C3	121.25 (9)	N1—C15—C16	111.32 (8)
C5—C4—H4	119.1 (7)	N1—C15—H15A	107.0 (7)
C3—C4—H4	119.6 (7)	C16—C15—H15A	113.3 (7)
C4—C5—C6	119.56 (9)	N1—C15—H15B	106.7 (6)
C4—C5—H5	120.1 (6)	C16—C15—H15B	111.3 (6)
C6—C5—H5	120.4 (6)	H15A—C15—H15B	106.9 (9)
N1—C6—C5	122.61 (8)	C17—C16—C15	110.98 (8)
N1—C6—C1	117.70 (7)	C17—C16—H16A	108.8 (7)
C5—C6—C1	119.68 (8)	C15—C16—H16A	108.4 (7)
O1—C7—N1	121.94 (8)	C17—C16—H16B	108.1 (7)
O1—C7—C8	122.62 (8)	C15—C16—H16B	112.4 (8)
N1—C7—C8	115.43 (7)	H16A—C16—H16B	108.1 (10)
N2—C8—C9	117.51 (8)	O2—C17—C16	107.93 (9)
N2—C8—C7	123.28 (8)	O2—C17—H17A	110.7 (7)
C9—C8—C7	119.21 (7)	C16—C17—H17A	114.0 (7)
C10—C9—C14	119.17 (8)	O2—C17—H17B	111.7 (8)
C10—C9—C8	121.63 (8)	C16—C17—H17B	109.1 (8)
C14—C9—C8	119.06 (8)	H17A—C17—H17B	103.5 (11)
C11—C10—C9	120.21 (9)

C8—N2—C1—C2	−176.53 (9)	C1—N2—C8—C7	−2.06 (14)
C8—N2—C1—C6	1.73 (13)	O1—C7—C8—N2	−179.52 (9)
N2—C1—C2—C3	177.28 (9)	N1—C7—C8—N2	−0.87 (13)
C6—C1—C2—C3	−1.03 (14)	O1—C7—C8—C9	0.91 (13)
C1—C2—C3—C4	0.79 (15)	N1—C7—C8—C9	179.56 (8)
C2—C3—C4—C5	−0.28 (15)	N2—C8—C9—C10	−135.20 (9)
C3—C4—C5—C6	0.01 (15)	C7—C8—C9—C10	44.40 (12)
C7—N1—C6—C5	174.33 (8)	N2—C8—C9—C14	40.45 (12)
C15—N1—C6—C5	−2.04 (13)	C7—C8—C9—C14	−139.95 (9)
C7—N1—C6—C1	−4.68 (13)	C14—C9—C10—C11	−0.85 (13)
C15—N1—C6—C1	178.95 (7)	C8—C9—C10—C11	174.79 (8)
C4—C5—C6—N1	−179.24 (8)	C9—C10—C11—C12	0.72 (14)
C4—C5—C6—C1	−0.25 (13)	C10—C11—C12—C13	0.31 (14)
N2—C1—C6—N1	1.55 (13)	C11—C12—C13—C14	−1.19 (14)
C2—C1—C6—N1	179.79 (8)	C12—C13—C14—C9	1.04 (14)
N2—C1—C6—C5	−177.49 (9)	C10—C9—C14—C13	−0.03 (14)
C2—C1—C6—C5	0.75 (13)	C8—C9—C14—C13	−175.78 (8)
C6—N1—C7—O1	−177.04 (8)	C7—N1—C15—C16	−91.26 (10)
C15—N1—C7—O1	−0.64 (13)	C6—N1—C15—C16	85.24 (10)
C6—N1—C7—C8	4.31 (12)	N1—C15—C16—C17	−168.64 (8)
C15—N1—C7—C8	−179.30 (8)	C15—C16—C17—O2	63.85 (11)
C1—N2—C8—C9	177.52 (8)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C9–C14 and C1–C6 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.949 (15)	1.888 (15)	2.8345 (10)	174.4 (14)
C15—H15A···O2ⁱⁱ	0.969 (11)	2.582 (12)	3.3425 (13)	135.5 (9)
C3—H3···Cg1ⁱⁱⁱ	0.953 (12)	2.734 (12)	3.4708 (12)	134.8 (9)
C10—H10···Cg2^iv	1.003 (12)	2.916 (13)	3.5859 (12)	124.9 (9)

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

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