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

Benzeid, H.; Saffon, N.; Garrigues, B.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536809039944

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2685

https://doi.org/10.1107/S1600536809039944

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

Hanane Benzeid,^a Nathalie Saffon,^b Bernard Garrigues,^c El Mokhtar Essassi ^a and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bService Commun Rayons X, Université Paul Sabatier, Bâtiment 2R1, 118 route de Narbonne, 31062 Toulouse, France, ^cHétérochimie Fondamentale et Appliquée, Université Paul Sabatier, UMR 5069, 118 Route de Narbonne, 31062 Toulouse, France, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 29 September 2009; accepted 1 October 2009; online 10 October 2009)

The ten-membered fused ring system in the title compound, C₂₁H₁₆N₂O₂, is planar (r.m.s. deviation = 0.03 Å). The phenyl substituent is aligned at 15.1 (1)° with respect to the mean plane through this system, whereas the phenyl ring of the benzyl substitutent is aligned at 84.4 (1)°.

Related literature

For the crystal structure of the unsubstituted quinolixalin-2(1H)-one, see: Padmaja et al. (1987 ); Stępień et al. (1976 ).

Experimental

Crystal data

C₂₁H₁₆N₂O
M_r = 312.36
Triclinic, $[P \overline 1]$
a = 5.4776 (2) Å
b = 12.7015 (3) Å
c = 12.7469 (4) Å
α = 62.260 (2)°
β = 89.963 (2)°
γ = 87.845 (2)°
V = 784.23 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 193 K
0.60 × 0.20 × 0.10 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: none
12094 measured reflections
3864 independent reflections
2613 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.123
S = 1.04
3864 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039944/tk2547sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039944/tk2547Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of the unsubstituted quinolixalin-2(1H)-one, see: Padmaja et al. (1987); Stępień et al. (1976).

Experimental top

To a solution of 3-phenylquinoxalin-2(1H)-one (1 g, 4.5 mmol) in N,N-dimethylformamide (20 ml) was added benzyl chloride (0.62 ml, 5.4 mmol), potassium carbonate (0.74 g; 5.4 mmol) and a catalytic quantity of tetra-n-butylammonium bromide. The mixture was stirred 24 h. The solution was filtered to remove the salts and the solvent then removed under reduced pressure. The residue was recrystallized from ethanol to afford yellow crystals in 85% yield.

Structure description top

For the crystal structure of the unsubstituted quinolixalin-2(1H)-one, see: Padmaja et al. (1987); Stępień et al. (1976).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₁H₁₆N₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₂₁H₁₆N₂O	Z = 2
M_r = 312.36	F(000) = 328
Triclinic, P1	D_x = 1.323 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4776 (2) Å	Cell parameters from 2441 reflections
b = 12.7015 (3) Å	θ = 5.4–28.3°
c = 12.7469 (4) Å	µ = 0.08 mm⁻¹
α = 62.260 (2)°	T = 193 K
β = 89.963 (2)°	Plate, yellow
γ = 87.845 (2)°	0.60 × 0.20 × 0.10 mm
V = 784.23 (4) Å³

Data collection top

Bruker APEX2 diffractometer	2613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 28.3°, θ_min = 5.1°
φ and ω scans	h = −7→7
12094 measured reflections	k = −14→16
3864 independent reflections	l = 0→16

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: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0537P)² + 0.0846P] where P = (F_o² + 2F_c²)/3
3864 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₁₆N₂O	γ = 87.845 (2)°
M_r = 312.36	V = 784.23 (4) Å³
Triclinic, P1	Z = 2
a = 5.4776 (2) Å	Mo Kα radiation
b = 12.7015 (3) Å	µ = 0.08 mm⁻¹
c = 12.7469 (4) Å	T = 193 K
α = 62.260 (2)°	0.60 × 0.20 × 0.10 mm
β = 89.963 (2)°

Data collection top

Bruker APEX2 diffractometer	2613 reflections with I > 2σ(I)
12094 measured reflections	R_int = 0.037
3864 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
3864 reflections	Δρ_min = −0.23 e Å⁻³
217 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.8050 (2)	0.89874 (9)	0.53919 (8)	0.0380 (3)
N1	1.1349 (2)	0.77023 (10)	0.59168 (9)	0.0277 (3)
N2	0.9967 (2)	0.67563 (10)	0.82777 (10)	0.0305 (3)
C1	0.9290 (3)	0.81877 (12)	0.61835 (12)	0.0280 (3)
C2	0.8775 (3)	0.76874 (12)	0.74735 (11)	0.0276 (3)
C3	0.6910 (3)	0.82891 (12)	0.78827 (12)	0.0286 (3)
C4	0.4926 (3)	0.89908 (12)	0.71895 (13)	0.0319 (3)
H4	0.4715	0.9110	0.6402	0.038*
C5	0.3266 (3)	0.95134 (14)	0.76436 (14)	0.0381 (4)
H5	0.1920	0.9985	0.7164	0.046*
C6	0.3539 (3)	0.93598 (14)	0.87820 (14)	0.0407 (4)
H6	0.2388	0.9722	0.9086	0.049*
C7	0.5508 (3)	0.86731 (14)	0.94800 (13)	0.0412 (4)
H7	0.5715	0.8567	1.0264	0.049*
C8	0.7170 (3)	0.81428 (13)	0.90366 (13)	0.0361 (4)
H8	0.8510	0.7672	0.9522	0.043*
C9	1.2618 (3)	0.66951 (12)	0.67667 (12)	0.0289 (3)
C10	1.1849 (3)	0.62205 (12)	0.79476 (12)	0.0296 (3)
C11	1.3073 (3)	0.52005 (13)	0.88251 (13)	0.0360 (4)
H11	1.2555	0.4871	0.9623	0.043*
C12	1.5020 (3)	0.46731 (14)	0.85381 (14)	0.0408 (4)
H12	1.5861	0.3990	0.9138	0.049*
C13	1.5755 (3)	0.51431 (14)	0.73642 (15)	0.0408 (4)
H13	1.7093	0.4774	0.7169	0.049*
C14	1.4563 (3)	0.61377 (13)	0.64823 (13)	0.0349 (3)
H14	1.5065	0.6443	0.5684	0.042*
C15	1.2157 (3)	0.82914 (12)	0.46821 (12)	0.0303 (3)
H15A	1.3964	0.8232	0.4678	0.036*
H15B	1.1655	0.9147	0.4322	0.036*
C16	1.1145 (2)	0.77719 (12)	0.39268 (12)	0.0274 (3)
C17	1.1725 (3)	0.82793 (14)	0.27348 (13)	0.0417 (4)
H17	1.2813	0.8915	0.2418	0.050*
C18	1.0730 (3)	0.78651 (16)	0.20034 (14)	0.0483 (4)
H18	1.1141	0.8222	0.1189	0.058*
C19	0.9165 (3)	0.69502 (15)	0.24384 (15)	0.0445 (4)
H19	0.8474	0.6678	0.1929	0.053*
C20	0.8597 (3)	0.64252 (16)	0.36247 (15)	0.0491 (4)
H20	0.7524	0.5783	0.3938	0.059*
C21	0.9601 (3)	0.68376 (14)	0.43620 (13)	0.0401 (4)
H21	0.9213	0.6467	0.5179	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0422 (6)	0.0378 (6)	0.0273 (5)	0.0079 (5)	−0.0037 (5)	−0.0103 (5)
N1	0.0307 (6)	0.0279 (6)	0.0243 (6)	−0.0009 (5)	−0.0005 (5)	−0.0120 (5)
N2	0.0353 (7)	0.0283 (6)	0.0267 (6)	−0.0012 (5)	−0.0012 (5)	−0.0119 (5)
C1	0.0310 (8)	0.0261 (7)	0.0278 (7)	−0.0022 (6)	−0.0023 (6)	−0.0131 (6)
C2	0.0300 (7)	0.0283 (7)	0.0256 (7)	−0.0054 (6)	−0.0005 (6)	−0.0131 (6)
C3	0.0298 (7)	0.0278 (7)	0.0287 (7)	−0.0050 (6)	0.0029 (6)	−0.0132 (6)
C4	0.0305 (8)	0.0334 (8)	0.0321 (7)	−0.0040 (6)	−0.0014 (6)	−0.0153 (6)
C5	0.0300 (8)	0.0397 (8)	0.0421 (9)	−0.0001 (6)	0.0016 (7)	−0.0170 (7)
C6	0.0407 (9)	0.0398 (9)	0.0409 (9)	−0.0013 (7)	0.0113 (7)	−0.0184 (7)
C7	0.0491 (10)	0.0446 (9)	0.0289 (7)	0.0022 (8)	0.0048 (7)	−0.0167 (7)
C8	0.0390 (9)	0.0388 (8)	0.0284 (7)	0.0037 (7)	−0.0009 (6)	−0.0143 (6)
C9	0.0302 (8)	0.0269 (7)	0.0311 (7)	−0.0025 (6)	−0.0047 (6)	−0.0149 (6)
C10	0.0309 (8)	0.0293 (7)	0.0303 (7)	−0.0010 (6)	−0.0041 (6)	−0.0153 (6)
C11	0.0417 (9)	0.0320 (8)	0.0306 (7)	0.0006 (7)	−0.0060 (7)	−0.0115 (6)
C12	0.0408 (9)	0.0324 (8)	0.0447 (9)	0.0068 (7)	−0.0106 (7)	−0.0147 (7)
C13	0.0341 (9)	0.0401 (9)	0.0518 (10)	0.0053 (7)	−0.0034 (7)	−0.0247 (8)
C14	0.0324 (8)	0.0370 (8)	0.0374 (8)	−0.0007 (6)	0.0013 (6)	−0.0192 (7)
C15	0.0319 (8)	0.0298 (7)	0.0275 (7)	−0.0049 (6)	0.0034 (6)	−0.0116 (6)
C16	0.0267 (7)	0.0283 (7)	0.0276 (7)	0.0025 (6)	0.0000 (6)	−0.0136 (6)
C17	0.0480 (10)	0.0441 (9)	0.0312 (8)	−0.0106 (8)	0.0083 (7)	−0.0155 (7)
C18	0.0596 (11)	0.0584 (11)	0.0299 (8)	−0.0017 (9)	0.0045 (8)	−0.0231 (8)
C19	0.0486 (10)	0.0516 (10)	0.0437 (9)	0.0048 (8)	−0.0100 (8)	−0.0316 (8)
C20	0.0533 (11)	0.0530 (10)	0.0497 (10)	−0.0177 (8)	0.0027 (8)	−0.0300 (9)
C21	0.0445 (9)	0.0464 (9)	0.0320 (8)	−0.0139 (7)	0.0068 (7)	−0.0197 (7)

Geometric parameters (Å, º) top

O1—C1	1.2274 (15)	C11—C12	1.376 (2)
N1—C1	1.3820 (18)	C11—H11	0.9500
N1—C9	1.3918 (17)	C12—C13	1.394 (2)
N1—C15	1.4698 (16)	C12—H12	0.9500
N2—C2	1.3000 (17)	C13—C14	1.379 (2)
N2—C10	1.3843 (18)	C13—H13	0.9500
C1—C2	1.4925 (18)	C14—H14	0.9500
C2—C3	1.4872 (19)	C15—C16	1.5132 (18)
C3—C4	1.3971 (19)	C15—H15A	0.9900
C3—C8	1.4008 (19)	C15—H15B	0.9900
C4—C5	1.383 (2)	C16—C21	1.376 (2)
C4—H4	0.9500	C16—C17	1.3887 (19)
C5—C6	1.379 (2)	C17—C18	1.386 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.387 (2)	C18—C19	1.366 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.382 (2)	C19—C20	1.380 (2)
C7—H7	0.9500	C19—H19	0.9500
C8—H8	0.9500	C20—C21	1.393 (2)
C9—C14	1.396 (2)	C20—H20	0.9500
C9—C10	1.4071 (19)	C21—H21	0.9500
C10—C11	1.4021 (19)

C1—N1—C9	122.23 (11)	C12—C11—H11	119.8
C1—N1—C15	117.13 (11)	C10—C11—H11	119.8
C9—N1—C15	120.63 (11)	C11—C12—C13	119.83 (14)
C2—N2—C10	119.69 (12)	C11—C12—H12	120.1
O1—C1—N1	120.56 (12)	C13—C12—H12	120.1
O1—C1—C2	124.30 (13)	C14—C13—C12	120.87 (15)
N1—C1—C2	115.13 (11)	C14—C13—H13	119.6
N2—C2—C3	117.57 (12)	C12—C13—H13	119.6
N2—C2—C1	122.49 (12)	C13—C14—C9	119.81 (14)
C3—C2—C1	119.89 (11)	C13—C14—H14	120.1
C4—C3—C8	118.12 (13)	C9—C14—H14	120.1
C4—C3—C2	124.19 (12)	N1—C15—C16	113.80 (11)
C8—C3—C2	117.69 (12)	N1—C15—H15A	108.8
C5—C4—C3	120.39 (13)	C16—C15—H15A	108.8
C5—C4—H4	119.8	N1—C15—H15B	108.8
C3—C4—H4	119.8	C16—C15—H15B	108.8
C6—C5—C4	120.92 (14)	H15A—C15—H15B	107.7
C6—C5—H5	119.5	C21—C16—C17	118.26 (13)
C4—C5—H5	119.5	C21—C16—C15	122.73 (12)
C5—C6—C7	119.48 (14)	C17—C16—C15	118.99 (13)
C5—C6—H6	120.3	C18—C17—C16	120.52 (15)
C7—C6—H6	120.3	C18—C17—H17	119.7
C8—C7—C6	120.05 (14)	C16—C17—H17	119.7
C8—C7—H7	120.0	C19—C18—C17	120.85 (15)
C6—C7—H7	120.0	C19—C18—H18	119.6
C7—C8—C3	121.03 (14)	C17—C18—H18	119.6
C7—C8—H8	119.5	C18—C19—C20	119.34 (15)
C3—C8—H8	119.5	C18—C19—H19	120.3
N1—C9—C14	122.46 (13)	C20—C19—H19	120.3
N1—C9—C10	117.81 (12)	C19—C20—C21	119.91 (16)
C14—C9—C10	119.71 (13)	C19—C20—H20	120.0
N2—C10—C11	118.79 (13)	C21—C20—H20	120.0
N2—C10—C9	121.84 (12)	C16—C21—C20	121.11 (14)
C11—C10—C9	119.33 (13)	C16—C21—H21	119.4
C12—C11—C10	120.43 (14)	C20—C21—H21	119.4

C9—N1—C1—O1	−171.38 (12)	C2—N2—C10—C11	−178.50 (12)
C15—N1—C1—O1	8.22 (18)	C2—N2—C10—C9	3.8 (2)
C9—N1—C1—C2	9.96 (18)	N1—C9—C10—N2	−2.82 (19)
C15—N1—C1—C2	−170.44 (11)	C14—C9—C10—N2	178.51 (12)
C10—N2—C2—C3	−175.06 (12)	N1—C9—C10—C11	179.47 (12)
C10—N2—C2—C1	2.35 (19)	C14—C9—C10—C11	0.8 (2)
O1—C1—C2—N2	172.36 (13)	N2—C10—C11—C12	−177.24 (13)
N1—C1—C2—N2	−9.05 (18)	C9—C10—C11—C12	0.5 (2)
O1—C1—C2—C3	−10.3 (2)	C10—C11—C12—C13	−1.1 (2)
N1—C1—C2—C3	168.30 (11)	C11—C12—C13—C14	0.4 (2)
N2—C2—C3—C4	−155.97 (13)	C12—C13—C14—C9	1.0 (2)
C1—C2—C3—C4	26.6 (2)	N1—C9—C14—C13	179.85 (13)
N2—C2—C3—C8	24.20 (19)	C10—C9—C14—C13	−1.5 (2)
C1—C2—C3—C8	−153.28 (13)	C1—N1—C15—C16	−92.98 (14)
C8—C3—C4—C5	−0.5 (2)	C9—N1—C15—C16	86.63 (15)
C2—C3—C4—C5	179.64 (13)	N1—C15—C16—C21	0.29 (19)
C3—C4—C5—C6	0.4 (2)	N1—C15—C16—C17	178.13 (13)
C4—C5—C6—C7	0.1 (2)	C21—C16—C17—C18	1.2 (2)
C5—C6—C7—C8	−0.4 (2)	C15—C16—C17—C18	−176.71 (14)
C6—C7—C8—C3	0.2 (2)	C16—C17—C18—C19	−0.1 (3)
C4—C3—C8—C7	0.2 (2)	C17—C18—C19—C20	−0.8 (3)
C2—C3—C8—C7	−179.92 (14)	C18—C19—C20—C21	0.6 (3)
C1—N1—C9—C14	174.04 (12)	C17—C16—C21—C20	−1.4 (2)
C15—N1—C9—C14	−5.54 (19)	C15—C16—C21—C20	176.43 (14)
C1—N1—C9—C10	−4.59 (18)	C19—C20—C21—C16	0.5 (3)
C15—N1—C9—C10	175.83 (12)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₂O
M_r	312.36
Crystal system, space group	Triclinic, P1
Temperature (K)	193
a, b, c (Å)	5.4776 (2), 12.7015 (3), 12.7469 (4)
α, β, γ (°)	62.260 (2), 89.963 (2), 87.845 (2)
V (Å³)	784.23 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.60 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEX2
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12094, 3864, 2613
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.123, 1.04
No. of reflections	3864
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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