2-Methyl-3-(4-methyl-phen-yl)-5,6-diphenyl-2,3-dihydro-pyrazine.

In the title mol-ecule, C(24)H(22)N(2), four atoms (N-C-C-N) of the heterocyclic ring, with their attached H atoms, and all atoms of the methyl group, are disordered over two positions; the site-occupancy factor of the major component is 0.713 (6). The major disorder component of the heterocyclic ring adopts a half-chair conformation, with all substituents equatorial. The benzene ring adjacent to the methyl group forms dihedral angles of 79.68 (11) and 80.92 (11)° with the phenyl rings; the dihedral angle between adjacent phenyl rings is 59.10 (11)°. The crystal structure features three C-H⋯π inter-actions.

Related literature

For the biological properties of dihydro­pyrazines and for closely related crystal structures, see: Anuradha et al. (2009 ▶, 2011 ▶).

Experimental

Crystal data

C24H22N2

M = 338.44

Monoclinic,

a = 8.1986 (5) Å

b = 11.8211 (6) Å

c = 19.6686 (7) Å

β = 93.638 (4)°

V = 1902.38 (17) Å3

Z = 4

Cu Kα radiation

μ = 0.53 mm−1

T = 123 K

0.39 × 0.21 × 0.17 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.830, T max = 1.000

12585 measured reflections

3892 independent reflections

3044 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.214

S = 1.07

3892 reflections

254 parameters

68 restraints

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041438/hg5255sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041438/hg5255Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041438/hg5255Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041438/hg5255Isup4.cml

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

C24H22N2	F(000) = 720
Mr = 338.44	Dx = 1.182 Mg m−3
Monoclinic, P21/c	Melting point: 450 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 8.1986 (5) Å	Cell parameters from 3179 reflections
b = 11.8211 (6) Å	θ = 3.7–75.3°
c = 19.6686 (7) Å	µ = 0.53 mm−1
β = 93.638 (4)°	T = 123 K
V = 1902.38 (17) Å3	Prism, colourless
Z = 4	0.39 × 0.21 × 0.17 mm

Agilent Xcalibur Ruby Gemini diffractometer	3892 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3044 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.5081 pixels mm-1	θmax = 75.5°, θmin = 4.4°
ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→14
Tmin = 0.830, Tmax = 1.000	l = −24→21
12585 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.214	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1119P)2 + 0.6381P] where P = (Fo2 + 2Fc2)/3
3892 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.71 e Å−3
68 restraints	Δρmin = −0.35 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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	Occ. (<1)
N1A	0.2620 (9)	0.8818 (4)	0.1306 (3)	0.0675 (11)	0.713 (6)
N2A	0.2421 (13)	0.9429 (5)	−0.0086 (3)	0.0781 (11)	0.713 (6)
C1	0.2458 (3)	0.80641 (19)	0.08145 (10)	0.0556 (7)
C2	0.2522 (3)	0.8383 (2)	0.00937 (11)	0.0604 (7)
C3A	0.2008 (6)	1.0239 (3)	0.04467 (17)	0.0605 (12)	0.713 (6)
C4A	0.2286 (11)	1.1422 (5)	0.0181 (4)	0.0792 (15)	0.713 (6)
C5A	0.3136 (7)	0.9952 (4)	0.1078 (2)	0.0682 (15)	0.713 (6)
C6	0.2095 (3)	0.68882 (18)	0.10250 (10)	0.0518 (6)
C7	0.2969 (3)	0.64263 (19)	0.15892 (11)	0.0548 (6)
C8	0.2641 (3)	0.53339 (19)	0.18009 (12)	0.0584 (7)
C9	0.1433 (3)	0.47028 (19)	0.14630 (11)	0.0590 (7)
C10	0.0534 (3)	0.5165 (2)	0.09150 (11)	0.0590 (7)
C11	0.0877 (3)	0.62512 (19)	0.06909 (10)	0.0553 (7)
C12	0.2806 (3)	0.75362 (19)	−0.04483 (11)	0.0566 (7)
C13	0.3907 (3)	0.6650 (2)	−0.03313 (11)	0.0601 (7)
C14	0.4185 (3)	0.5879 (2)	−0.08442 (13)	0.0666 (8)
C15	0.3345 (3)	0.5981 (2)	−0.14751 (12)	0.0664 (8)
C16	0.2262 (3)	0.6859 (2)	−0.16006 (12)	0.0649 (8)
C17	0.1998 (3)	0.7640 (2)	−0.10907 (11)	0.0617 (7)
C18	0.2782 (4)	1.0771 (2)	0.16632 (11)	0.0667 (8)
C19	0.3912 (3)	1.16373 (19)	0.17894 (12)	0.0636 (8)
C20	0.3719 (3)	1.24072 (18)	0.23056 (11)	0.0562 (7)
C21	0.2402 (3)	1.23338 (19)	0.27160 (10)	0.0548 (7)
C22	0.1289 (3)	1.1477 (2)	0.25858 (12)	0.0644 (8)
C23	0.1480 (3)	1.0702 (2)	0.20701 (12)	0.0685 (8)
C24	0.2223 (4)	1.3153 (2)	0.32921 (13)	0.0775 (10)
N1B	0.291 (3)	0.8782 (12)	0.1267 (9)	0.0675 (11)	0.287 (6)
N2B	0.220 (4)	0.9433 (14)	−0.0092 (8)	0.0781 (11)	0.287 (6)
C3B	0.2792 (15)	1.0317 (8)	0.0396 (4)	0.0605 (12)	0.287 (6)
C4B	0.195 (3)	1.1406 (13)	0.0178 (12)	0.0792 (15)	0.287 (6)
C5B	0.2419 (19)	0.9953 (10)	0.1111 (5)	0.0682 (15)	0.287 (6)
H7A	0.37917	0.68605	0.18298	0.0657*
H8A	0.32533	0.50200	0.21814	0.0701*
H1A	0.08386	1.01444	0.05527	0.0724*	0.713 (6)
H2A	0.15954	1.15427	−0.02381	0.1186*	0.713 (6)
H3A	0.20059	1.19772	0.05242	0.1186*	0.713 (6)
H4A	0.34371	1.15099	0.00839	0.1186*	0.713 (6)
H5A	0.43148	0.99642	0.09751	0.0819*	0.713 (6)
H15A	0.35169	0.54430	−0.18224	0.0797*
H16A	0.16954	0.69305	−0.20351	0.0778*
H17A	0.12614	0.82504	−0.11808	0.0740*
H19A	0.48250	1.16990	0.15174	0.0763*
H20A	0.44973	1.29963	0.23819	0.0675*
H22A	0.03708	1.14176	0.28552	0.0772*
H23A	0.07014	1.01130	0.19956	0.0822*
H24A	0.10614	1.32498	0.33688	0.1160*
H24B	0.27968	1.28581	0.37071	0.1160*
H24C	0.26928	1.38848	0.31757	0.1160*
H9A	0.12204	0.39527	0.16064	0.0708*
H10A	−0.03236	0.47404	0.06897	0.0708*
H11A	0.02715	0.65567	0.03060	0.0663*
H13A	0.44729	0.65724	0.01028	0.0720*
H14A	0.49501	0.52833	−0.07626	0.0798*
H6B	0.39999	1.04078	0.03728	0.0724*	0.287 (6)
H7B	0.12757	1.12787	−0.02437	0.1186*	0.287 (6)
H8B	0.12589	1.16604	0.05365	0.1186*	0.287 (6)
H9B	0.27751	1.19846	0.01009	0.1186*	0.287 (6)
H10B	0.11982	0.99121	0.10842	0.0819*	0.287 (6)

	U11	U22	U33	U12	U13	U23
N1A	0.109 (3)	0.0531 (11)	0.0414 (12)	−0.0068 (14)	0.0131 (15)	0.0041 (9)
N2A	0.130 (3)	0.0623 (12)	0.0421 (10)	0.0090 (15)	0.0068 (13)	0.0061 (9)
C1	0.0714 (13)	0.0551 (11)	0.0412 (10)	0.0034 (10)	0.0114 (9)	0.0037 (8)
C2	0.0792 (14)	0.0596 (12)	0.0427 (10)	0.0019 (11)	0.0074 (10)	0.0046 (9)
C3A	0.079 (3)	0.0616 (15)	0.0408 (12)	−0.006 (2)	0.0041 (17)	0.0034 (11)
C4A	0.107 (4)	0.0719 (16)	0.0580 (14)	0.006 (2)	0.001 (2)	0.0083 (12)
C5A	0.109 (4)	0.0531 (13)	0.0435 (13)	0.002 (2)	0.012 (2)	0.0063 (10)
C6	0.0628 (12)	0.0521 (11)	0.0420 (10)	0.0023 (9)	0.0151 (8)	0.0009 (8)
C7	0.0601 (11)	0.0573 (12)	0.0477 (10)	−0.0011 (10)	0.0090 (9)	0.0031 (9)
C8	0.0653 (13)	0.0580 (12)	0.0532 (12)	0.0075 (10)	0.0149 (10)	0.0097 (10)
C9	0.0693 (13)	0.0523 (11)	0.0581 (12)	−0.0006 (10)	0.0247 (10)	0.0006 (9)
C10	0.0647 (12)	0.0634 (13)	0.0508 (11)	−0.0094 (10)	0.0192 (10)	−0.0084 (10)
C11	0.0634 (12)	0.0632 (12)	0.0403 (10)	0.0030 (10)	0.0112 (9)	−0.0014 (9)
C12	0.0698 (13)	0.0591 (12)	0.0424 (10)	−0.0054 (10)	0.0150 (9)	0.0026 (9)
C13	0.0699 (13)	0.0636 (13)	0.0483 (11)	−0.0033 (11)	0.0167 (10)	0.0029 (10)
C14	0.0758 (14)	0.0649 (14)	0.0622 (13)	−0.0046 (12)	0.0299 (11)	−0.0002 (11)
C15	0.0770 (14)	0.0694 (14)	0.0561 (13)	−0.0192 (12)	0.0293 (11)	−0.0120 (10)
C16	0.0688 (13)	0.0823 (16)	0.0451 (11)	−0.0186 (12)	0.0166 (10)	−0.0057 (10)
C17	0.0686 (13)	0.0726 (14)	0.0451 (11)	−0.0058 (11)	0.0132 (10)	0.0018 (10)
C18	0.111 (2)	0.0513 (12)	0.0378 (10)	−0.0028 (12)	0.0060 (11)	0.0081 (9)
C19	0.0850 (15)	0.0542 (12)	0.0542 (12)	0.0065 (11)	0.0249 (11)	0.0092 (9)
C20	0.0645 (12)	0.0511 (11)	0.0539 (11)	0.0012 (10)	0.0101 (9)	0.0056 (9)
C21	0.0672 (12)	0.0562 (12)	0.0416 (10)	0.0042 (10)	0.0093 (9)	0.0067 (9)
C22	0.0682 (13)	0.0724 (15)	0.0539 (12)	−0.0063 (12)	0.0141 (10)	0.0115 (11)
C23	0.0898 (17)	0.0626 (13)	0.0522 (12)	−0.0185 (12)	−0.0031 (12)	0.0072 (10)
C24	0.104 (2)	0.0758 (16)	0.0554 (13)	0.0010 (15)	0.0260 (13)	−0.0034 (12)
N1B	0.109 (3)	0.0531 (11)	0.0414 (12)	−0.0068 (14)	0.0131 (15)	0.0041 (9)
N2B	0.130 (3)	0.0623 (12)	0.0421 (10)	0.0090 (15)	0.0068 (13)	0.0061 (9)
C3B	0.079 (3)	0.0616 (15)	0.0408 (12)	−0.006 (2)	0.0041 (17)	0.0034 (11)
C4B	0.107 (4)	0.0719 (16)	0.0580 (14)	0.006 (2)	0.001 (2)	0.0083 (12)
C5B	0.109 (4)	0.0531 (13)	0.0435 (13)	0.002 (2)	0.012 (2)	0.0063 (10)

N1A—C1	1.315 (6)	C20—C21	1.391 (3)
N1A—C5A	1.484 (7)	C21—C22	1.376 (3)
N1B—C5B	1.47 (2)	C21—C24	1.505 (3)
N1B—C1	1.268 (17)	C22—C23	1.383 (3)
N2A—C3A	1.475 (7)	C3A—H1A	1.0000
N2A—C2	1.287 (6)	C3B—H6B	1.0000
N2B—C2	1.316 (17)	C4A—H3A	0.9800
N2B—C3B	1.48 (2)	C4A—H4A	0.9800
C1—C6	1.486 (3)	C4A—H2A	0.9800
C1—C2	1.471 (3)	C4B—H7B	0.9800
C2—C12	1.491 (3)	C4B—H8B	0.9800
C3A—C4A	1.515 (7)	C4B—H9B	0.9800
C3A—C5A	1.538 (6)	C5A—H5A	1.0000
C3B—C4B	1.51 (2)	C5B—H10B	1.0000
C3B—C5B	1.520 (13)	C7—H7A	0.9500
C5A—C18	1.546 (5)	C8—H8A	0.9500
C5B—C18	1.470 (11)	C9—H9A	0.9500
C6—C7	1.394 (3)	C10—H10A	0.9500
C6—C11	1.383 (3)	C11—H11A	0.9500
C7—C8	1.388 (3)	C13—H13A	0.9500
C8—C9	1.377 (3)	C14—H14A	0.9500
C9—C10	1.379 (3)	C15—H15A	0.9500
C10—C11	1.392 (3)	C16—H16A	0.9500
C12—C13	1.392 (3)	C17—H17A	0.9500
C12—C17	1.394 (3)	C19—H19A	0.9500
C13—C14	1.389 (3)	C20—H20A	0.9500
C14—C15	1.386 (3)	C22—H22A	0.9500
C15—C16	1.378 (3)	C23—H23A	0.9500
C16—C17	1.390 (3)	C24—H24B	0.9800
C18—C19	1.393 (4)	C24—H24C	0.9800
C18—C23	1.377 (4)	C24—H24A	0.9800
C19—C20	1.380 (3)
C1—N1A—C5A	114.1 (4)	C5A—C3A—H1A	110.00
C1—N1B—C5B	114.9 (14)	C5B—C3B—H6B	109.00
C2—N2A—C3A	116.3 (5)	N2B—C3B—H6B	109.00
C2—N2B—C3B	115.7 (14)	C4B—C3B—H6B	109.00
N1A—C1—C6	116.2 (3)	C3A—C4A—H3A	110.00
C2—C1—C6	121.89 (19)	H2A—C4A—H4A	109.00
N1B—C1—C6	119.0 (7)	C3A—C4A—H4A	109.00
N1B—C1—C2	118.6 (8)	H2A—C4A—H3A	110.00
N1A—C1—C2	121.8 (3)	C3A—C4A—H2A	109.00
N2A—C2—C1	120.3 (3)	H3A—C4A—H4A	110.00
N2B—C2—C1	119.4 (8)	C3B—C4B—H7B	109.00
N2B—C2—C12	118.2 (7)	C3B—C4B—H9B	109.00
N2A—C2—C12	117.3 (3)	H7B—C4B—H8B	110.00
C1—C2—C12	122.3 (2)	C3B—C4B—H8B	109.00
C4A—C3A—C5A	112.7 (4)	H8B—C4B—H9B	109.00
N2A—C3A—C4A	107.9 (4)	H7B—C4B—H9B	110.00
N2A—C3A—C5A	106.1 (4)	C3A—C5A—H5A	112.00
N2B—C3B—C4B	107.0 (14)	C18—C5A—H5A	112.00
N2B—C3B—C5B	108.9 (11)	N1A—C5A—H5A	112.00
C4B—C3B—C5B	112.9 (12)	C18—C5B—H10B	103.00
C3A—C5A—C18	109.4 (4)	C3B—C5B—H10B	103.00
N1A—C5A—C3A	106.0 (4)	N1B—C5B—H10B	103.00
N1A—C5A—C18	105.7 (4)	C8—C7—H7A	120.00
N1B—C5B—C18	115.2 (10)	C6—C7—H7A	120.00
C3B—C5B—C18	117.0 (9)	C7—C8—H8A	120.00
N1B—C5B—C3B	113.1 (11)	C9—C8—H8A	120.00
C7—C6—C11	119.0 (2)	C10—C9—H9A	120.00
C1—C6—C7	119.1 (2)	C8—C9—H9A	120.00
C1—C6—C11	121.89 (19)	C9—C10—H10A	120.00
C6—C7—C8	120.2 (2)	C11—C10—H10A	120.00
C7—C8—C9	120.4 (2)	C6—C11—H11A	120.00
C8—C9—C10	119.7 (2)	C10—C11—H11A	120.00
C9—C10—C11	120.3 (2)	C12—C13—H13A	120.00
C6—C11—C10	120.4 (2)	C14—C13—H13A	120.00
C2—C12—C13	121.1 (2)	C15—C14—H14A	120.00
C2—C12—C17	120.1 (2)	C13—C14—H14A	120.00
C13—C12—C17	118.8 (2)	C14—C15—H15A	120.00
C12—C13—C14	120.5 (2)	C16—C15—H15A	120.00
C13—C14—C15	119.9 (2)	C17—C16—H16A	120.00
C14—C15—C16	120.3 (2)	C15—C16—H16A	120.00
C15—C16—C17	119.9 (2)	C12—C17—H17A	120.00
C12—C17—C16	120.6 (2)	C16—C17—H17A	120.00
C5A—C18—C19	116.1 (3)	C18—C19—H19A	120.00
C5A—C18—C23	125.8 (3)	C20—C19—H19A	120.00
C19—C18—C23	118.1 (2)	C21—C20—H20A	119.00
C5B—C18—C19	135.8 (6)	C19—C20—H20A	119.00
C5B—C18—C23	105.2 (6)	C21—C22—H22A	119.00
C18—C19—C20	120.7 (2)	C23—C22—H22A	119.00
C19—C20—C21	121.0 (2)	C18—C23—H23A	119.00
C20—C21—C22	117.9 (2)	C22—C23—H23A	120.00
C20—C21—C24	120.9 (2)	H24B—C24—H24C	109.00
C22—C21—C24	121.2 (2)	H24A—C24—H24B	109.00
C21—C22—C23	121.3 (2)	H24A—C24—H24C	109.00
C18—C23—C22	121.0 (2)	C21—C24—H24A	109.00
N2A—C3A—H1A	110.00	C21—C24—H24B	109.00
C4A—C3A—H1A	110.00	C21—C24—H24C	109.00
C5A—N1A—C1—C2	−9.5 (7)	C3A—C5A—C18—C23	77.9 (4)
C5A—N1A—C1—C6	174.5 (4)	C1—C6—C7—C8	179.3 (2)
C1—N1A—C5A—C18	164.4 (5)	C11—C6—C7—C8	1.4 (3)
C1—N1A—C5A—C3A	48.4 (7)	C1—C6—C11—C10	−177.9 (2)
C3A—N2A—C2—C1	−8.4 (10)	C7—C6—C11—C10	−0.1 (3)
C2—N2A—C3A—C5A	47.6 (9)	C6—C7—C8—C9	−1.1 (4)
C2—N2A—C3A—C4A	168.7 (7)	C7—C8—C9—C10	−0.6 (4)
C3A—N2A—C2—C12	175.2 (5)	C8—C9—C10—C11	1.9 (4)
C6—C1—C2—C12	−21.6 (4)	C9—C10—C11—C6	−1.6 (3)
N1A—C1—C6—C7	−44.7 (5)	C2—C12—C13—C14	−178.8 (2)
N1A—C1—C2—C12	162.6 (4)	C17—C12—C13—C14	−0.5 (4)
C6—C1—C2—N2A	162.2 (6)	C2—C12—C17—C16	179.6 (2)
N1A—C1—C6—C11	133.2 (4)	C13—C12—C17—C16	1.3 (4)
C2—C1—C6—C11	−42.8 (3)	C12—C13—C14—C15	−0.9 (4)
N1A—C1—C2—N2A	−13.6 (7)	C13—C14—C15—C16	1.5 (4)
C2—C1—C6—C7	139.4 (2)	C14—C15—C16—C17	−0.6 (4)
N2A—C2—C12—C13	137.5 (6)	C15—C16—C17—C12	−0.8 (4)
N2A—C2—C12—C17	−40.8 (6)	C5A—C18—C19—C20	−179.3 (3)
C1—C2—C12—C17	143.0 (2)	C23—C18—C19—C20	−0.5 (4)
C1—C2—C12—C13	−38.8 (4)	C5A—C18—C23—C22	179.4 (3)
N2A—C3A—C5A—N1A	−66.7 (6)	C19—C18—C23—C22	0.6 (4)
C4A—C3A—C5A—C18	61.9 (6)	C18—C19—C20—C21	0.5 (4)
N2A—C3A—C5A—C18	179.8 (4)	C19—C20—C21—C22	−0.7 (3)
C4A—C3A—C5A—N1A	175.4 (5)	C19—C20—C21—C24	178.1 (2)
N1A—C5A—C18—C19	143.0 (4)	C20—C21—C22—C23	0.9 (3)
N1A—C5A—C18—C23	−35.7 (5)	C24—C21—C22—C23	−177.9 (2)
C3A—C5A—C18—C19	−103.3 (4)	C21—C22—C23—C18	−0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cg4i	0.95	2.95	3.743 (3)	142
C19—H19A···Cg4ii	0.95	2.77	3.578 (3)	143
C22—H22A···Cg3iii	0.95	2.66	3.590 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C6–C11 and C12–C17 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cg4i	0.95	2.95	3.743 (3)	142
C19—H19A⋯Cg4ii	0.95	2.77	3.578 (3)	143
C22—H22A⋯Cg3iii	0.95	2.66	3.590 (3)	165

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