1-Benzyl-3-phenyl-quinoxalin-2(1H)-one.

The ten-membered fused ring system in the title compound, C(21)H(16)N(2)O(2), 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 = 312.36

Triclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.123

S = 1.04

3864 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039944/tk2547Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H16N2O	Z = 2
Mr = 312.36	F(000) = 328
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0537P)2 + 0.0846P] where P = (Fo2 + 2Fc2)/3
3864 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)