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

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

doi:10.1107/S160053680903414X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2323

doi:10.1107/S160053680903414X

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

Hanane Benzeid,^a El Mokhtar Essassi,^a Nathalie Saffon,^b Bernard Garrigues ^c 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 24 August 2009; accepted 26 August 2009; online 5 September 2009)

The phenyl substituents in both independent molecules of the title compound, C₁₅H₁₂N₂O, 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_r = 236.27
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.114
S = 1.01
4682 reflections
327 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903414X/sj2638sup1.cif

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

checkCIF report

Related literature top

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

Experimental top

3-Phenylquinoxalin-2(1H)-one (1 g, 4.5 mmol), methyl iodide (0.31 ml, 5.0 mmol), potassium carbonate (0.7 g, 5.0 mmol) and a catalytic quantity of tetra-n-butylammonium bromide were stirred in N,N-dimethylformamide (20 ml) for 24 h. The mixture was filtered to remove the salts and the solvent removed under reduce pressure. The residue was recrystallized in ethanol to afford the pure compound in 80% yield.The formulation was established by proton and carbon-13 NMR spectroscopy in CDCl₃.

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. A thermal ellipsoid plot (Barbour, 2001) of the two unique molecules of C₁₅H₁₆N₂O₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₁₅H₁₂N₂O	F(000) = 992
M_r = 236.27	D_x = 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

Data collection top

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

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0498P)² + 0.4004P] where P = (F_o² + 2F_c²)/3
4682 reflections	(Δ/σ)_max = 0.001
327 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O	V = 2312.32 (12) Å³
M_r = 236.27	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.3919 (5) Å	µ = 0.09 mm⁻¹
b = 7.0775 (2) Å	T = 193 K
c = 20.0214 (6) Å	0.60 × 0.20 × 0.10 mm
β = 95.434 (2)°

Data collection top

Bruker APEX2 diffractometer	3068 reflections with I > 2σ(I)
31360 measured reflections	R_int = 0.054
4682 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
4682 reflections	Δρ_min = −0.18 e Å⁻³
327 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O
M_r	236.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	193
a, b, c (Å)	16.3919 (5), 7.0775 (2), 20.0214 (6)
β (°)	95.434 (2)
V (Å³)	2312.32 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEX2 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	31360, 4682, 3068
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 1.01
No. of reflections	4682
No. of parameters	327
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

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
Benzeid, H., Vendier, L., Ramli, Y., Garrigues, B. & Essassi, E. M. (2008). Acta Cryst. E64, o2234. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar