N'-(3-Methyl-quinoxalin-2-yl)-N'-phenyl-benzohydrazide.

In the crystal structure of the title compound, C(22)H(18)N(4)O, the quinoxaline system makes dihedral angles of 86.59 (7) and 63.37 (9)° with the benzohydrazide and phenyl rings, respectively. The benzohydrazide ring makes a dihedral angle of 72.46 (10)° with the phenyl ring. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds, C-H⋯O contacts and C-H⋯π inter-actions.

Related literature

For the biological activity of quinoxaline derivatives, see: Kleim et al. (1995 ▶). For the anti­tumour and anti­tuberculous properties of quinoxaline derivatives, see: Abasolo et al. (1987 ▶); Rodrigo et al. (2002 ▶). For inter­esting anti­fungal, herbicidal, anti­dyslipidemic and anti­oxidative activities of quinoxaline derivatives, see: Jampilek et al. (2005 ▶); Sashidhara et al. (2009 ▶); Watkins et al. (2009 ▶).

Experimental

Crystal data

C22H18N4O

M = 354.40

Monoclinic,

a = 18.6809 (12) Å

b = 10.5840 (8) Å

c = 9.5860 (6) Å

β = 100.108 (3)°

V = 1865.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.35 × 0.34 × 0.18 mm

Data collection

Bruker APEXII CCD detector diffractometer

19397 measured reflections

4502 independent reflections

2286 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.01

4502 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.20 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101703X/bt5532sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101703X/bt5532Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101703X/bt5532Isup3.mol

Supplementary material file. DOI: 10.1107/S160053681101703X/bt5532Isup4.cml

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

C22H18N4O	F(000) = 744
Mr = 354.40	Dx = 1.262 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 345 reflections
a = 18.6809 (12) Å	θ = 2.7–26.8°
b = 10.5840 (8) Å	µ = 0.08 mm−1
c = 9.5860 (6) Å	T = 296 K
β = 100.108 (3)°	Prism, colourless
V = 1865.9 (2) Å3	0.35 × 0.34 × 0.18 mm
Z = 4

Bruker APEXII CCD detector diffractometer	2286 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 28.0°, θmin = 1.1°
ω and φ scans	h = −24→24
19397 measured reflections	k = −8→13
4502 independent reflections	l = −12→10

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0573P)2] where P = (Fo2 + 2Fc2)/3
4502 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. The data collection nominally covered a sphere of reciprocal space, by a combination of two sets of exposures; each set had a different φ angle for the crystal and each exposure covered 0.5° in ω and 30 s in time. The crystal-to-detector distance was 37.5 mm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

	x	y	z	Uiso*/Ueq
N1	0.26330 (7)	0.48128 (13)	0.36620 (14)	0.0485 (4)
N2	0.16619 (8)	0.65538 (14)	0.21427 (16)	0.0568 (4)
N3	0.20960 (7)	0.31873 (13)	0.22361 (14)	0.0480 (4)
O1	0.30401 (6)	0.31707 (11)	0.04356 (12)	0.0578 (3)
C8	0.38609 (8)	0.17788 (14)	0.18621 (16)	0.0439 (4)
C7	0.31928 (8)	0.25585 (14)	0.15321 (16)	0.0415 (4)
C21	0.26800 (9)	0.60703 (16)	0.39925 (18)	0.0494 (4)
N4	0.27553 (7)	0.25367 (12)	0.25080 (13)	0.0465 (3)
H6	0.2880	0.2128	0.3288	0.056*
C14	0.21230 (8)	0.44722 (15)	0.26227 (17)	0.0437 (4)
C15	0.16273 (8)	0.53545 (17)	0.18063 (17)	0.0488 (4)
C16	0.21862 (9)	0.69384 (16)	0.32436 (19)	0.0524 (4)
C6	0.14703 (9)	0.24218 (16)	0.21688 (17)	0.0483 (4)
C20	0.32204 (10)	0.65006 (19)	0.5091 (2)	0.0669 (5)
H20	0.3549	0.5931	0.5588	0.080*
C13	0.39464 (10)	0.08112 (17)	0.28516 (18)	0.0595 (5)
H13	0.3579	0.0650	0.3368	0.071*
C22	0.11033 (9)	0.49634 (18)	0.05163 (19)	0.0671 (5)
H22A	0.0695	0.4544	0.0797	0.101*
H22B	0.1340	0.4398	−0.0040	0.101*
H22C	0.0937	0.5697	−0.0036	0.101*
C17	0.22522 (11)	0.82237 (18)	0.3608 (2)	0.0722 (6)
H17	0.1934	0.8811	0.3116	0.087*
C1	0.08899 (9)	0.28171 (18)	0.27791 (19)	0.0597 (5)
H1	0.0921	0.3569	0.3288	0.072*
C19	0.32655 (12)	0.7747 (2)	0.5432 (2)	0.0783 (6)
H19	0.3621	0.8024	0.6172	0.094*
C9	0.44130 (10)	0.19941 (18)	0.1104 (2)	0.0680 (5)
H9	0.4366	0.2633	0.0428	0.082*
C5	0.14310 (10)	0.12638 (18)	0.14787 (18)	0.0647 (5)
H5	0.1821	0.0976	0.1083	0.078*
C12	0.45673 (13)	0.0085 (2)	0.3081 (2)	0.0784 (6)
H12	0.4617	−0.0562	0.3747	0.094*
C18	0.27851 (12)	0.8610 (2)	0.4687 (2)	0.0800 (7)
H18	0.2826	0.9462	0.4925	0.096*
C3	0.02217 (13)	0.0973 (3)	0.1942 (3)	0.0912 (7)
H3	−0.0202	0.0496	0.1845	0.109*
C11	0.51074 (12)	0.0315 (2)	0.2334 (3)	0.0920 (8)
H11	0.5527	−0.0174	0.2492	0.110*
C2	0.02629 (11)	0.2097 (2)	0.2635 (2)	0.0786 (6)
H2	−0.0132	0.2385	0.3015	0.094*
C4	0.08056 (14)	0.0540 (2)	0.1384 (2)	0.0846 (7)
H4	0.0781	−0.0244	0.0940	0.102*
C10	0.50361 (11)	0.1261 (2)	0.1350 (3)	0.0936 (7)
H10	0.5408	0.1413	0.0842	0.112*

	U11	U22	U33	U12	U13	U23
N1	0.0488 (8)	0.0440 (9)	0.0508 (9)	−0.0024 (6)	0.0038 (7)	−0.0003 (7)
N2	0.0587 (10)	0.0500 (9)	0.0627 (10)	0.0109 (7)	0.0132 (8)	0.0060 (8)
N3	0.0438 (8)	0.0416 (8)	0.0578 (9)	0.0045 (6)	0.0069 (6)	−0.0038 (7)
O1	0.0811 (9)	0.0501 (7)	0.0434 (7)	0.0102 (6)	0.0140 (6)	0.0074 (6)
C8	0.0494 (10)	0.0392 (9)	0.0430 (9)	0.0002 (7)	0.0078 (8)	−0.0100 (8)
C7	0.0550 (10)	0.0329 (8)	0.0367 (9)	−0.0027 (7)	0.0085 (8)	−0.0046 (7)
C21	0.0529 (11)	0.0451 (10)	0.0525 (10)	−0.0055 (8)	0.0155 (9)	−0.0019 (9)
N4	0.0519 (8)	0.0461 (8)	0.0425 (8)	0.0109 (7)	0.0108 (6)	0.0039 (6)
C14	0.0434 (9)	0.0433 (10)	0.0463 (10)	0.0012 (7)	0.0130 (8)	−0.0007 (8)
C15	0.0464 (10)	0.0515 (11)	0.0491 (10)	0.0040 (8)	0.0102 (8)	0.0025 (8)
C16	0.0593 (11)	0.0452 (11)	0.0568 (11)	0.0018 (8)	0.0211 (9)	−0.0004 (9)
C6	0.0535 (11)	0.0469 (10)	0.0420 (9)	−0.0038 (8)	0.0014 (8)	0.0021 (8)
C20	0.0673 (13)	0.0631 (13)	0.0680 (13)	−0.0137 (10)	0.0057 (10)	−0.0070 (10)
C13	0.0703 (12)	0.0569 (12)	0.0530 (11)	0.0181 (9)	0.0151 (9)	0.0026 (9)
C22	0.0625 (12)	0.0742 (14)	0.0594 (12)	0.0054 (10)	−0.0036 (9)	0.0084 (10)
C17	0.0926 (16)	0.0447 (12)	0.0864 (15)	0.0049 (10)	0.0350 (13)	−0.0032 (11)
C1	0.0585 (12)	0.0592 (12)	0.0619 (12)	−0.0044 (9)	0.0119 (9)	0.0024 (9)
C19	0.0889 (16)	0.0694 (16)	0.0789 (15)	−0.0287 (12)	0.0211 (12)	−0.0173 (12)
C9	0.0633 (13)	0.0635 (13)	0.0811 (14)	−0.0031 (10)	0.0237 (11)	−0.0011 (11)
C5	0.0803 (14)	0.0571 (12)	0.0537 (11)	−0.0069 (10)	0.0030 (10)	−0.0043 (10)
C12	0.0894 (16)	0.0696 (15)	0.0717 (14)	0.0300 (12)	0.0017 (13)	−0.0025 (11)
C18	0.1086 (18)	0.0520 (13)	0.0909 (17)	−0.0234 (13)	0.0488 (15)	−0.0208 (13)
C3	0.0790 (17)	0.101 (2)	0.0875 (17)	−0.0368 (14)	−0.0014 (13)	0.0133 (15)
C11	0.0630 (15)	0.0860 (18)	0.119 (2)	0.0220 (13)	−0.0057 (14)	−0.0242 (16)
C2	0.0630 (14)	0.0899 (17)	0.0824 (15)	−0.0134 (12)	0.0112 (11)	0.0153 (13)
C4	0.1145 (19)	0.0618 (14)	0.0688 (14)	−0.0309 (14)	−0.0081 (13)	−0.0045 (11)
C10	0.0595 (14)	0.0962 (19)	0.133 (2)	−0.0001 (13)	0.0396 (14)	−0.0130 (17)

N1—C14	1.3028 (19)	C22—H22A	0.9600
N1—C21	1.367 (2)	C22—H22B	0.9600
N2—C15	1.308 (2)	C22—H22C	0.9600
N2—C16	1.370 (2)	C17—C18	1.366 (3)
N3—N4	1.3951 (16)	C17—H17	0.9300
N3—C14	1.408 (2)	C1—C2	1.384 (2)
N3—C6	1.414 (2)	C1—H1	0.9300
O1—C7	1.2251 (17)	C19—C18	1.388 (3)
C8—C9	1.381 (2)	C19—H19	0.9300
C8—C13	1.386 (2)	C9—C10	1.385 (3)
C8—C7	1.483 (2)	C9—H9	0.9300
C7—N4	1.3461 (18)	C5—C4	1.387 (3)
C21—C20	1.401 (2)	C5—H5	0.9300
C21—C16	1.406 (2)	C12—C11	1.358 (3)
N4—H6	0.8600	C12—H12	0.9300
C14—C15	1.445 (2)	C18—H18	0.9300
C15—C22	1.495 (2)	C3—C2	1.358 (3)
C16—C17	1.405 (2)	C3—C4	1.375 (3)
C6—C1	1.384 (2)	C3—H3	0.9300
C6—C5	1.389 (2)	C11—C10	1.366 (3)
C20—C19	1.358 (3)	C11—H11	0.9300
C20—H20	0.9300	C2—H2	0.9300
C13—C12	1.376 (2)	C4—H4	0.9300
C13—H13	0.9300	C10—H10	0.9300
C14—N1—C21	117.07 (14)	H22A—C22—H22C	109.5
C15—N2—C16	118.43 (14)	H22B—C22—H22C	109.5
N4—N3—C14	115.97 (12)	C18—C17—C16	119.9 (2)
N4—N3—C6	114.91 (13)	C18—C17—H17	120.0
C14—N3—C6	123.80 (13)	C16—C17—H17	120.0
C9—C8—C13	118.36 (16)	C2—C1—C6	120.24 (19)
C9—C8—C7	118.30 (16)	C2—C1—H1	119.9
C13—C8—C7	123.28 (15)	C6—C1—H1	119.9
O1—C7—N4	121.80 (14)	C20—C19—C18	120.6 (2)
O1—C7—C8	122.53 (14)	C20—C19—H19	119.7
N4—C7—C8	115.66 (14)	C18—C19—H19	119.7
N1—C21—C20	119.94 (17)	C8—C9—C10	120.1 (2)
N1—C21—C16	120.52 (16)	C8—C9—H9	120.0
C20—C21—C16	119.53 (17)	C10—C9—H9	120.0
C7—N4—N3	119.04 (13)	C4—C5—C6	119.50 (19)
C7—N4—H6	120.5	C4—C5—H5	120.3
N3—N4—H6	120.5	C6—C5—H5	120.3
N1—C14—N3	117.14 (14)	C11—C12—C13	120.0 (2)
N1—C14—C15	123.27 (15)	C11—C12—H12	120.0
N3—C14—C15	119.46 (14)	C13—C12—H12	120.0
N2—C15—C14	119.62 (15)	C17—C18—C19	120.8 (2)
N2—C15—C22	118.00 (15)	C17—C18—H18	119.6
C14—C15—C22	122.24 (16)	C19—C18—H18	119.6
N2—C16—C17	119.95 (17)	C2—C3—C4	120.1 (2)
N2—C16—C21	121.02 (16)	C2—C3—H3	119.9
C17—C16—C21	118.99 (18)	C4—C3—H3	119.9
C1—C6—C5	119.22 (17)	C12—C11—C10	120.3 (2)
C1—C6—N3	120.67 (15)	C12—C11—H11	119.9
C5—C6—N3	120.11 (16)	C10—C11—H11	119.9
C19—C20—C21	120.2 (2)	C3—C2—C1	120.4 (2)
C19—C20—H20	119.9	C3—C2—H2	119.8
C21—C20—H20	119.9	C1—C2—H2	119.8
C12—C13—C8	120.95 (19)	C3—C4—C5	120.5 (2)
C12—C13—H13	119.5	C3—C4—H4	119.8
C8—C13—H13	119.5	C5—C4—H4	119.8
C15—C22—H22A	109.5	C11—C10—C9	120.4 (2)
C15—C22—H22B	109.5	C11—C10—H10	119.8
H22A—C22—H22B	109.5	C9—C10—H10	119.8
C15—C22—H22C	109.5
C21—N1—C14—N3	177.02 (16)	O1—C7—C8—C9	16.7 (3)
C21—N1—C14—C15	1.5 (3)	O1—C7—C8—C13	−160.64 (18)
C14—N1—C21—C16	0.9 (3)	N4—C7—C8—C9	−164.24 (18)
C14—N1—C21—C20	−179.40 (18)	N4—C7—C8—C13	18.4 (3)
C16—N2—C15—C14	1.8 (3)	C7—C8—C9—C10	−178.0 (2)
C16—N2—C15—C22	−174.01 (17)	C13—C8—C9—C10	−0.5 (3)
C15—N2—C16—C17	178.2 (2)	C7—C8—C13—C12	177.6 (2)
C15—N2—C16—C21	0.4 (3)	C9—C8—C13—C12	0.3 (3)
C6—N3—N4—C7	117.98 (18)	C8—C9—C10—C11	0.4 (4)
C14—N3—N4—C7	−86.8 (2)	C9—C10—C11—C12	−0.1 (5)
N4—N3—C6—C1	138.71 (18)	C10—C11—C12—C13	−0.2 (5)
N4—N3—C6—C5	−41.6 (2)	C11—C12—C13—C8	0.1 (4)
C14—N3—C6—C1	−14.3 (3)	N1—C14—C15—N2	−2.9 (3)
C14—N3—C6—C5	165.36 (18)	N1—C14—C15—C22	172.71 (17)
N4—N3—C14—N1	−27.4 (2)	N3—C14—C15—N2	−178.39 (17)
N4—N3—C14—C15	148.32 (16)	N3—C14—C15—C22	−2.8 (3)
C6—N3—C14—N1	125.33 (19)	N2—C16—C17—C18	−178.6 (2)
C6—N3—C14—C15	−58.9 (2)	C21—C16—C17—C18	−0.8 (3)
N3—N4—C7—O1	2.7 (3)	N2—C16—C21—N1	−1.9 (3)
N3—N4—C7—C8	−176.34 (15)	N2—C16—C21—C20	178.37 (19)
C6—C1—C2—C3	2.7 (4)	C17—C16—C21—N1	−179.65 (19)
C2—C1—C6—N3	176.1 (2)	C17—C16—C21—C20	0.6 (3)
C2—C1—C6—C5	−3.6 (3)	C16—C17—C18—C19	0.0 (4)
C1—C2—C3—C4	0.1 (4)	C17—C18—C19—C20	1.0 (4)
C2—C3—C4—C5	−2.1 (4)	C18—C19—C20—C21	−1.2 (4)
C3—C4—C5—C6	1.2 (4)	C19—C20—C21—N1	−179.4 (2)
C4—C5—C6—N3	−178.0 (2)	C19—C20—C21—C16	0.4 (3)
C4—C5—C6—C1	1.6 (3)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H6···O1i	0.86	2.05	2.863 (2)	157.
C18—H18···O1ii	0.93	2.57	3.496 (3)	175.
C22—H22B···Cg1iii	0.96	2.99	3.696 (2)	131
C20—H20···Cg2iv	0.93	2.94	3.866 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H6⋯O1i	0.86	2.05	2.863 (2)	157
C18—H18⋯O1ii	0.93	2.57	3.496 (3)	175
C22—H22B⋯Cg1iii	0.96	2.99	3.696 (2)	131
C20—H20⋯Cg2iv	0.93	2.94	3.866 (2)	175

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .