2-Methyl-3-(4-methyl­phen­yl)-5,6-diphenyl-2,3-dihydro­pyrazine

Thiruvalluvar, A.; Anuradha, N.; Chitra, S.; Devanathan, D.; Butcher, R.J.

doi:10.1107/S1600536812041438

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3084

doi:10.1107/S1600536812041438

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2-Methyl-3-(4-methylphenyl)-5,6-diphenyl-2,3-dihydropyrazine

A. Thiruvalluvar,^a ^* N. Anuradha,^a S. Chitra,^b D. Devanathan ^c and R. J. Butcher ^d

^aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, KSR College of Engineering, KSR Kalvi Nagar, Tiruchengode 637 215, Tamilnadu, India, ^cDepartment of Chemistry, Government Arts College, C. Mutlur 608 102, Chidambaram, Tamilnadu, India, and ^dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 28 September 2012; accepted 2 October 2012; online 6 October 2012)

In the title molecule, C₂₄H₂₂N₂, 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 interactions.

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_r = 338.44
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.069
wR(F²) = 0.214
S = 1.07
3892 reflections
254 parameters
68 restraints
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) -x, -y+1, -z; (ii) -x+1, -y+2, -z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812041438/hg5255sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812041438/hg5255Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812041438/hg5255Isup4.cml

checkCIF report

Comment top

As part of our investigations of dihydropyrazine derivatives (Anuradha et al., 2009, 2011) to compare their chemical and biological activities, we have undertaken the X-ray crystal structure analysis of the title compound.

In the title molecule, C₂₄H₂₂N₂, Fig.1., the heterocyclic ring with the major disorder component, adopts a half-chair conformation, with all substituents equatorial. The phenyl ring at C1 makes a dihedral angle of 59.10 (11) and 79.68 (11)° with the phenyl ring at C2 and benzene ring at C5A respectively. The dihedral angle between the phenyl ring at C2 and benzene ring at C5A is 80.92 (11)°. Four atoms (N2—C3—C5—N1) of the heterocyclic ring, with their attached H atoms, and all atoms of the methyl group, are disordered over two positions; the site occupancy factors refined to 0.713 (6) and 0.287 (6). The crystal structure is stabilized by three C—H···π interactions (Table 1). No hydrogen bonds are found in the crystal structure.

Related literature top

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

Experimental top

To a homogeneous solution of benzil (1.05 g, 0.005 mol) and 1-methyl-2-(4'-methylphenyl)-ethanediaminedihydrochloride (1.29 g, 0.005 mol) in ethanol (20 ml), sodium acetate trihydrate (2.04 g, 0.015 mol) was added. The precipitated sodium chloride was filtered off and the filtrate was refluxed for 2 h. On completion of the reaction, as indicated by TLC, the reaction mixture was poured into crushed ice and the resulting solid was filtered and purified by column chromatography on silica gel. Elution with benzene-petroleum ether (4:1 v/v) at 333–353 K gave the pure product. Yield 1.60 g (72%). The pure product was recrystallized in ethyl acetate, to obtain crystals suitable for X-ray diffraction studies.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius. Only the major disorder component is shown.

2-Methyl-3-(4-methylphenyl)-5,6-diphenyl-2,3-dihydropyrazine top

Crystal data top

C₂₄H₂₂N₂	F(000) = 720
M_r = 338.44	D_x = 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

Data collection top

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

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.214	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1119P)² + 0.6381P] where P = (F_o² + 2F_c²)/3
3892 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.71 e Å⁻³
68 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₄H₂₂N₂	V = 1902.38 (17) Å³
M_r = 338.44	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.1986 (5) Å	µ = 0.53 mm⁻¹
b = 11.8211 (6) Å	T = 123 K
c = 19.6686 (7) Å	0.39 × 0.21 × 0.17 mm
β = 93.638 (4)°

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	3892 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3044 reflections with I > 2σ(I)
T_min = 0.830, T_max = 1.000	R_int = 0.028
12585 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	68 restraints
wR(F²) = 0.214	H-atom parameters constrained
S = 1.07	Δρ_max = 0.71 e Å⁻³
3892 reflections	Δρ_min = −0.35 e Å⁻³
254 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂N₂
M_r	338.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	8.1986 (5), 11.8211 (6), 19.6686 (7)
β (°)	93.638 (4)
V (Å³)	1902.38 (17)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.39 × 0.21 × 0.17

Data collection
Diffractometer	Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.830, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12585, 3892, 3044
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.214, 1.07
No. of reflections	3892
No. of parameters	254
No. of restraints	68
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.35

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x, y+1/2, −z+1/2.

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Anuradha, N., Chitra, S., Thiruvalluvar, A., Pandiarajan, K., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o2598. Web of Science CSD CrossRef IUCr Journals Google Scholar
Anuradha, N., Thiruvalluvar, A., Pandiarajan, K., Chitra, S. & Butcher, R. J. (2009). Acta Cryst. E65, o546. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3084

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