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

The phenyl substituents in both independent mol-ecules of the title compound, C(15)H(12)N(2)O, are twisted with respect to the quinoxaline system [dihedral angles = 19.3 (1) and 30.4 (1)°].

Related literature

For the structure of 1-ethyl-3-methyl­quinoxalin-2(1H)-one, see: Benzeid et al. (2008 ▶).

Experimental

Crystal data

C15H12N2O

M = 236.27

Monoclinic,

a = 16.3919 (5) Å

b = 7.0775 (2) Å

c = 20.0214 (6) Å

β = 95.434 (2)°

V = 2312.32 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 193 K

0.60 × 0.20 × 0.10 mm

Data collection

Bruker APEX2 diffractometer

Absorption correction: none

31360 measured reflections

4682 independent reflections

3068 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.114

S = 1.01

4682 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.18 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/S160053680903414X/sj2638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903414X/sj2638Isup2.hkl

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

C15H12N2O	F(000) = 992
Mr = 236.27	Dx = 1.357 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4338 reflections
a = 16.3919 (5) Å	θ = 2.5–24.9°
b = 7.0775 (2) Å	µ = 0.09 mm−1
c = 20.0214 (6) Å	T = 193 K
β = 95.434 (2)°	Plate, yellow
V = 2312.32 (12) Å3	0.60 × 0.20 × 0.10 mm
Z = 8

Bruker APEX2 diffractometer	3068 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
graphite	θmax = 26.4°, θmin = 5.2°
φ and ω scans	h = −20→20
31360 measured reflections	k = −8→8
4682 independent reflections	l = −25→24

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.4004P] where P = (Fo2 + 2Fc2)/3
4682 reflections	(Δ/σ)max = 0.001
327 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.53417 (7)	0.34744 (19)	0.19948 (6)	0.0472 (4)
O2	0.62711 (8)	0.8355 (2)	0.09382 (7)	0.0632 (4)
N1	0.42018 (8)	0.3190 (2)	0.12599 (7)	0.0323 (3)
N2	0.33162 (8)	0.2202 (2)	0.23283 (6)	0.0326 (3)
N3	0.69753 (8)	0.8664 (2)	0.19620 (7)	0.0358 (4)
N4	0.54955 (8)	0.86008 (19)	0.25385 (7)	0.0317 (3)
C1	0.46011 (10)	0.3149 (2)	0.18965 (9)	0.0331 (4)
C2	0.40856 (10)	0.2669 (2)	0.24408 (8)	0.0300 (4)
C3	0.44373 (10)	0.2670 (2)	0.31523 (8)	0.0309 (4)
C4	0.50477 (10)	0.3928 (3)	0.34009 (9)	0.0389 (4)
H4	0.5281	0.4779	0.3105	0.047*
C5	0.53143 (11)	0.3938 (3)	0.40790 (9)	0.0435 (5)
H5	0.5728	0.4802	0.4246	0.052*
C6	0.49836 (11)	0.2705 (3)	0.45122 (9)	0.0453 (5)
H6	0.5169	0.2722	0.4976	0.054*
C7	0.43825 (11)	0.1445 (3)	0.42723 (9)	0.0418 (5)
H7	0.4157	0.0590	0.4571	0.050*
C8	0.41091 (10)	0.1428 (2)	0.35977 (8)	0.0364 (4)
H8	0.3694	0.0562	0.3435	0.044*
C9	0.46906 (12)	0.3662 (3)	0.07079 (9)	0.0464 (5)
H9A	0.4507	0.4876	0.0512	0.070*
H9B	0.4622	0.2674	0.0364	0.070*
H9C	0.5270	0.3751	0.0878	0.070*
C10	0.33732 (10)	0.2762 (2)	0.11315 (8)	0.0306 (4)
C11	0.29496 (10)	0.2221 (2)	0.16767 (8)	0.0309 (4)
C12	0.21273 (10)	0.1659 (3)	0.15667 (9)	0.0382 (4)
H12	0.1844	0.1259	0.1935	0.046*
C13	0.17287 (11)	0.1683 (3)	0.09346 (9)	0.0428 (5)
H13	0.1173	0.1291	0.0862	0.051*
C14	0.21443 (12)	0.2287 (3)	0.03988 (9)	0.0438 (5)
H14	0.1863	0.2334	−0.0038	0.053*
C15	0.29569 (11)	0.2818 (2)	0.04900 (8)	0.0380 (4)
H15	0.3232	0.3221	0.0118	0.046*
C16	0.62597 (11)	0.8499 (3)	0.15482 (9)	0.0382 (4)
C17	0.54917 (10)	0.8488 (2)	0.18917 (8)	0.0309 (4)
C18	0.46772 (10)	0.8295 (2)	0.14974 (8)	0.0312 (4)
C19	0.45321 (12)	0.8707 (3)	0.08144 (9)	0.0407 (4)
H19	0.4969	0.9137	0.0573	0.049*
C20	0.37535 (13)	0.8491 (3)	0.04856 (10)	0.0472 (5)
H20	0.3661	0.8780	0.0021	0.057*
C21	0.31130 (12)	0.7860 (3)	0.08274 (10)	0.0469 (5)
H21	0.2584	0.7694	0.0597	0.056*
C22	0.32428 (11)	0.7471 (3)	0.15040 (10)	0.0441 (5)
H22	0.2802	0.7051	0.1742	0.053*
C23	0.40153 (10)	0.7693 (2)	0.18359 (9)	0.0369 (4)
H23	0.4098	0.7432	0.2303	0.044*
C24	0.77511 (11)	0.8735 (3)	0.16470 (10)	0.0487 (5)
H24A	0.7635	0.8699	0.1158	0.073*
H24B	0.8091	0.7647	0.1795	0.073*
H24C	0.8043	0.9905	0.1778	0.073*
C25	0.69876 (10)	0.8736 (2)	0.26575 (9)	0.0341 (4)
C26	0.62318 (10)	0.8714 (2)	0.29362 (8)	0.0314 (4)
C27	0.62170 (11)	0.8786 (3)	0.36323 (9)	0.0402 (4)
H27	0.5707	0.8792	0.3821	0.048*
C28	0.69355 (12)	0.8848 (3)	0.40451 (10)	0.0479 (5)
H28	0.6923	0.8890	0.4518	0.057*
C29	0.76810 (12)	0.8850 (3)	0.37677 (10)	0.0499 (5)
H29	0.8176	0.8885	0.4055	0.060*
C30	0.77140 (11)	0.8802 (3)	0.30840 (10)	0.0437 (5)
H30	0.8229	0.8813	0.2902	0.052*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (7)	0.0654 (9)	0.0483 (8)	−0.0051 (6)	0.0063 (6)	−0.0005 (7)
O2	0.0531 (9)	0.1003 (13)	0.0387 (8)	0.0090 (8)	0.0178 (7)	−0.0003 (8)
N1	0.0342 (8)	0.0341 (8)	0.0294 (8)	−0.0007 (6)	0.0075 (6)	−0.0014 (6)
N2	0.0297 (8)	0.0389 (8)	0.0288 (8)	−0.0005 (7)	0.0010 (6)	−0.0027 (6)
N3	0.0315 (8)	0.0342 (8)	0.0439 (9)	0.0005 (7)	0.0150 (7)	−0.0008 (7)
N4	0.0310 (7)	0.0315 (8)	0.0330 (8)	0.0001 (6)	0.0052 (6)	−0.0016 (6)
C1	0.0288 (9)	0.0313 (9)	0.0396 (10)	0.0018 (7)	0.0047 (8)	−0.0034 (8)
C2	0.0278 (9)	0.0288 (9)	0.0334 (9)	0.0018 (7)	0.0023 (7)	−0.0033 (7)
C3	0.0241 (8)	0.0348 (9)	0.0334 (9)	0.0041 (7)	0.0007 (7)	−0.0022 (8)
C4	0.0324 (9)	0.0425 (11)	0.0415 (11)	0.0004 (8)	0.0018 (8)	−0.0024 (8)
C5	0.0340 (10)	0.0506 (12)	0.0439 (11)	0.0010 (9)	−0.0061 (8)	−0.0103 (9)
C6	0.0403 (11)	0.0583 (13)	0.0354 (10)	0.0099 (10)	−0.0061 (8)	−0.0055 (10)
C7	0.0387 (10)	0.0496 (12)	0.0366 (10)	0.0058 (9)	0.0004 (8)	0.0066 (9)
C8	0.0311 (9)	0.0396 (10)	0.0376 (10)	−0.0010 (8)	−0.0009 (8)	0.0008 (8)
C9	0.0509 (11)	0.0492 (12)	0.0417 (11)	−0.0096 (10)	0.0174 (9)	−0.0008 (9)
C10	0.0336 (9)	0.0266 (9)	0.0315 (9)	0.0030 (7)	0.0029 (7)	−0.0033 (7)
C11	0.0303 (9)	0.0321 (9)	0.0298 (9)	0.0032 (7)	0.0014 (7)	−0.0035 (7)
C12	0.0308 (9)	0.0485 (11)	0.0350 (10)	0.0004 (8)	0.0015 (8)	−0.0013 (8)
C13	0.0319 (10)	0.0520 (12)	0.0427 (11)	0.0014 (9)	−0.0059 (8)	−0.0030 (9)
C14	0.0457 (11)	0.0479 (12)	0.0353 (10)	0.0051 (9)	−0.0089 (9)	−0.0018 (9)
C15	0.0479 (11)	0.0362 (10)	0.0300 (9)	0.0010 (9)	0.0036 (8)	0.0008 (8)
C16	0.0401 (10)	0.0398 (11)	0.0361 (10)	0.0026 (8)	0.0110 (8)	0.0025 (8)
C17	0.0362 (9)	0.0241 (9)	0.0332 (10)	0.0025 (7)	0.0082 (7)	−0.0006 (7)
C18	0.0353 (9)	0.0259 (9)	0.0326 (9)	0.0056 (7)	0.0045 (7)	−0.0030 (7)
C19	0.0489 (11)	0.0371 (10)	0.0363 (10)	0.0060 (9)	0.0046 (9)	−0.0018 (8)
C20	0.0572 (13)	0.0453 (12)	0.0367 (10)	0.0127 (10)	−0.0077 (10)	−0.0053 (9)
C21	0.0431 (11)	0.0407 (11)	0.0538 (13)	0.0071 (9)	−0.0109 (10)	−0.0133 (9)
C22	0.0370 (10)	0.0414 (11)	0.0533 (12)	−0.0002 (9)	0.0004 (9)	−0.0040 (9)
C23	0.0359 (10)	0.0364 (10)	0.0381 (10)	0.0020 (8)	0.0017 (8)	−0.0015 (8)
C24	0.0368 (10)	0.0467 (12)	0.0666 (13)	−0.0015 (9)	0.0262 (10)	−0.0030 (10)
C25	0.0331 (9)	0.0252 (9)	0.0445 (10)	0.0003 (7)	0.0066 (8)	−0.0002 (8)
C26	0.0293 (9)	0.0280 (9)	0.0372 (10)	0.0016 (7)	0.0044 (7)	−0.0008 (7)
C27	0.0383 (10)	0.0439 (11)	0.0384 (10)	0.0012 (9)	0.0040 (8)	−0.0013 (8)
C28	0.0502 (12)	0.0499 (12)	0.0417 (11)	0.0009 (10)	−0.0058 (9)	−0.0030 (9)
C29	0.0405 (11)	0.0478 (12)	0.0582 (13)	0.0006 (9)	−0.0116 (10)	−0.0024 (10)
C30	0.0301 (10)	0.0380 (11)	0.0631 (13)	−0.0019 (8)	0.0049 (9)	−0.0008 (9)

O1—C1	1.2331 (19)	C12—H12	0.9500
O2—C16	1.228 (2)	C13—C14	1.391 (3)
N1—C1	1.377 (2)	C13—H13	0.9500
N1—C10	1.392 (2)	C14—C15	1.380 (2)
N1—C9	1.464 (2)	C14—H14	0.9500
N2—C2	1.3027 (19)	C15—H15	0.9500
N2—C11	1.384 (2)	C16—C17	1.491 (2)
N3—C16	1.376 (2)	C17—C18	1.491 (2)
N3—C25	1.392 (2)	C18—C19	1.396 (2)
N3—C24	1.473 (2)	C18—C23	1.399 (2)
N4—C17	1.297 (2)	C19—C20	1.388 (3)
N4—C26	1.384 (2)	C19—H19	0.9500
C1—C2	1.480 (2)	C20—C21	1.381 (3)
C2—C3	1.485 (2)	C20—H20	0.9500
C3—C4	1.395 (2)	C21—C22	1.379 (3)
C3—C8	1.396 (2)	C21—H21	0.9500
C4—C5	1.386 (2)	C22—C23	1.382 (2)
C4—H4	0.9500	C22—H22	0.9500
C5—C6	1.377 (3)	C23—H23	0.9500
C5—H5	0.9500	C24—H24A	0.9800
C6—C7	1.381 (3)	C24—H24B	0.9800
C6—H6	0.9500	C24—H24C	0.9800
C7—C8	1.382 (2)	C25—C30	1.399 (2)
C7—H7	0.9500	C25—C26	1.406 (2)
C8—H8	0.9500	C26—C27	1.397 (2)
C9—H9A	0.9800	C27—C28	1.374 (2)
C9—H9B	0.9800	C27—H27	0.9500
C9—H9C	0.9800	C28—C29	1.389 (3)
C10—C15	1.397 (2)	C28—H28	0.9500
C10—C11	1.401 (2)	C29—C30	1.376 (3)
C11—C12	1.402 (2)	C29—H29	0.9500
C12—C13	1.368 (2)	C30—H30	0.9500
C1—N1—C10	122.44 (14)	C13—C14—H14	119.4
C1—N1—C9	117.23 (14)	C14—C15—C10	119.70 (17)
C10—N1—C9	120.31 (14)	C14—C15—H15	120.1
C2—N2—C11	119.18 (14)	C10—C15—H15	120.1
C16—N3—C25	122.45 (14)	O2—C16—N3	120.92 (16)
C16—N3—C24	117.81 (15)	O2—C16—C17	123.49 (16)
C25—N3—C24	119.73 (15)	N3—C16—C17	115.58 (15)
C17—N4—C26	119.98 (14)	N4—C17—C16	122.41 (15)
O1—C1—N1	121.22 (15)	N4—C17—C18	116.98 (15)
O1—C1—C2	123.17 (16)	C16—C17—C18	120.59 (15)
N1—C1—C2	115.60 (14)	C19—C18—C23	118.03 (16)
N2—C2—C1	122.79 (15)	C19—C18—C17	124.07 (16)
N2—C2—C3	116.58 (14)	C23—C18—C17	117.89 (15)
C1—C2—C3	120.62 (14)	C20—C19—C18	120.34 (18)
C4—C3—C8	118.73 (15)	C20—C19—H19	119.8
C4—C3—C2	122.86 (15)	C18—C19—H19	119.8
C8—C3—C2	118.31 (15)	C21—C20—C19	120.59 (18)
C5—C4—C3	120.11 (17)	C21—C20—H20	119.7
C5—C4—H4	119.9	C19—C20—H20	119.7
C3—C4—H4	119.9	C22—C21—C20	119.84 (18)
C6—C5—C4	120.47 (18)	C22—C21—H21	120.1
C6—C5—H5	119.8	C20—C21—H21	120.1
C4—C5—H5	119.8	C21—C22—C23	119.92 (19)
C5—C6—C7	120.04 (17)	C21—C22—H22	120.0
C5—C6—H6	120.0	C23—C22—H22	120.0
C7—C6—H6	120.0	C22—C23—C18	121.26 (17)
C6—C7—C8	120.00 (18)	C22—C23—H23	119.4
C6—C7—H7	120.0	C18—C23—H23	119.4
C8—C7—H7	120.0	N3—C24—H24A	109.5
C7—C8—C3	120.65 (16)	N3—C24—H24B	109.5
C7—C8—H8	119.7	H24A—C24—H24B	109.5
C3—C8—H8	119.7	N3—C24—H24C	109.5
N1—C9—H9A	109.5	H24A—C24—H24C	109.5
N1—C9—H9B	109.5	H24B—C24—H24C	109.5
H9A—C9—H9B	109.5	N3—C25—C30	122.88 (16)
N1—C9—H9C	109.5	N3—C25—C26	117.83 (15)
H9A—C9—H9C	109.5	C30—C25—C26	119.28 (17)
H9B—C9—H9C	109.5	N4—C26—C27	118.65 (15)
N1—C10—C15	123.16 (15)	N4—C26—C25	121.70 (15)
N1—C10—C11	117.56 (14)	C27—C26—C25	119.65 (16)
C15—C10—C11	119.28 (16)	C28—C27—C26	120.42 (17)
N2—C11—C10	122.27 (15)	C28—C27—H27	119.8
N2—C11—C12	118.07 (15)	C26—C27—H27	119.8
C10—C11—C12	119.66 (15)	C27—C28—C29	119.73 (18)
C13—C12—C11	120.63 (17)	C27—C28—H28	120.1
C13—C12—H12	119.7	C29—C28—H28	120.1
C11—C12—H12	119.7	C30—C29—C28	121.12 (18)
C12—C13—C14	119.40 (17)	C30—C29—H29	119.4
C12—C13—H13	120.3	C28—C29—H29	119.4
C14—C13—H13	120.3	C29—C30—C25	119.79 (17)
C15—C14—C13	121.25 (17)	C29—C30—H30	120.1
C15—C14—H14	119.4	C25—C30—H30	120.1
C10—N1—C1—O1	177.65 (15)	C25—N3—C16—O2	−176.73 (17)
C9—N1—C1—O1	−0.8 (2)	C24—N3—C16—O2	2.3 (3)
C10—N1—C1—C2	−1.6 (2)	C25—N3—C16—C17	2.6 (2)
C9—N1—C1—C2	179.90 (15)	C24—N3—C16—C17	−178.34 (15)
C11—N2—C2—C1	−2.6 (2)	C26—N4—C17—C16	−0.8 (2)
C11—N2—C2—C3	178.43 (14)	C26—N4—C17—C18	177.68 (14)
O1—C1—C2—N2	−175.20 (16)	O2—C16—C17—N4	178.43 (17)
N1—C1—C2—N2	4.1 (2)	N3—C16—C17—N4	−0.9 (2)
O1—C1—C2—C3	3.7 (3)	O2—C16—C17—C18	0.0 (3)
N1—C1—C2—C3	−177.04 (14)	N3—C16—C17—C18	−179.32 (14)
N2—C2—C3—C4	−147.10 (16)	N4—C17—C18—C19	160.36 (16)
C1—C2—C3—C4	33.9 (2)	C16—C17—C18—C19	−21.2 (2)
N2—C2—C3—C8	29.2 (2)	N4—C17—C18—C23	−18.6 (2)
C1—C2—C3—C8	−149.75 (16)	C16—C17—C18—C23	159.91 (15)
C8—C3—C4—C5	−0.4 (3)	C23—C18—C19—C20	−0.9 (2)
C2—C3—C4—C5	175.90 (16)	C17—C18—C19—C20	−179.88 (16)
C3—C4—C5—C6	0.3 (3)	C18—C19—C20—C21	−0.3 (3)
C4—C5—C6—C7	0.1 (3)	C19—C20—C21—C22	1.2 (3)
C5—C6—C7—C8	−0.4 (3)	C20—C21—C22—C23	−0.8 (3)
C6—C7—C8—C3	0.3 (3)	C21—C22—C23—C18	−0.5 (3)
C4—C3—C8—C7	0.1 (3)	C19—C18—C23—C22	1.3 (3)
C2—C3—C8—C7	−176.37 (15)	C17—C18—C23—C22	−179.67 (15)
C1—N1—C10—C15	179.25 (15)	C16—N3—C25—C30	176.49 (16)
C9—N1—C10—C15	−2.3 (2)	C24—N3—C25—C30	−2.5 (2)
C1—N1—C10—C11	−1.9 (2)	C16—N3—C25—C26	−2.6 (2)
C9—N1—C10—C11	176.53 (15)	C24—N3—C25—C26	178.38 (15)
C2—N2—C11—C10	−1.3 (2)	C17—N4—C26—C27	−178.43 (16)
C2—N2—C11—C12	178.21 (15)	C17—N4—C26—C25	0.9 (2)
N1—C10—C11—N2	3.5 (2)	N3—C25—C26—N4	0.8 (2)
C15—C10—C11—N2	−177.55 (15)	C30—C25—C26—N4	−178.34 (15)
N1—C10—C11—C12	−175.94 (15)	N3—C25—C26—C27	−179.93 (16)
C15—C10—C11—C12	3.0 (2)	C30—C25—C26—C27	0.9 (2)
N2—C11—C12—C13	178.77 (16)	N4—C26—C27—C28	178.28 (16)
C10—C11—C12—C13	−1.7 (3)	C25—C26—C27—C28	−1.0 (3)
C11—C12—C13—C14	−0.6 (3)	C26—C27—C28—C29	0.4 (3)
C12—C13—C14—C15	1.6 (3)	C27—C28—C29—C30	0.4 (3)
C13—C14—C15—C10	−0.3 (3)	C28—C29—C30—C25	−0.5 (3)
N1—C10—C15—C14	176.88 (16)	N3—C25—C30—C29	−179.29 (17)
C11—C10—C15—C14	−2.0 (2)	C26—C25—C30—C29	−0.2 (3)