2-Methyl-3,5,6-triphenyl-2,3-dihydro­pyrazine

Anuradha, N.; Thiruvalluvar, A.; Pandiarajan, K.; Chitra, S.; Butcher, R.J.

doi:10.1107/S1600536809005042

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o546

doi:10.1107/S1600536809005042

Open

access

2-Methyl-3,5,6-triphenyl-2,3-dihydropyrazine

N. Anuradha,^a A. Thiruvalluvar,^a ^* K. Pandiarajan,^b S. Chitra ^b and R. J. Butcher ^c

^aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, ^bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: athiru@vsnl.net

(Received 10 February 2009; accepted 11 February 2009; online 18 February 2009)

In the title molecule, C₂₃H₂₀N₂, the heterocyclic ring adopts a screw-boat conformation, with all substituents equatorial. The phenyl ring at position 3 makes dihedral angles of 78.12 (15) and 72.67 (15)°, respectively, with the phenyl rings at positions 5 and 6; the dihedral angle between the phenyl rings at positions 5 and 6 is 67.32 (14)°. A C—H⋯π interaction is present in the crystal structure.

Related literature

Some 2-alkyl-3,5,6-triphenyl-2,3-dihydropyrazines have been reported to exhibit fluorescence in the solid-state, see: Baliah & Pandiarajan (1978 ). For the use of dihydropyrazines in medicine, in particular with reference to DNA breakage activity, see: Yamaguchi et al. (2003 ). For their biological activity, see: Takechi et al. (2004 ) and their cyclooxygenase inhibitory activity, see: Singh et al. (2004 ).

Experimental

Crystal data

C₂₃H₂₀N₂
M_r = 324.41
Triclinic, $[P \overline 1]$
a = 10.4406 (10) Å
b = 10.5753 (7) Å
c = 11.0810 (13) Å
α = 93.439 (8)°
β = 114.161 (10)°
γ = 118.343 (9)°
V = 931.9 (2) Å³
Z = 2
Cu Kα radiation
μ = 0.52 mm⁻¹
T = 295 K
0.41 × 0.36 × 0.28 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.831, T_max = 0.885
8513 measured reflections
3852 independent reflections
3195 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.086
wR(F²) = 0.270
S = 1.09
3852 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C65—H65⋯Cgⁱ	0.93	2.97	3.834 (3)	156
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); 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/S1600536809005042/tk2373sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005042/tk2373Isup2.hkl

checkCIF report

Comment top

Some 2-alkyl-3,5,6-triphenyl-2,3-dihydropyrazines have been reported to exhibit fluorescence in the solid-state (Baliah & Pandiarajan, 1978). Dihydropyrazines are used in medicine, in particular with reference to DNA breakage activity (Yamaguchi et al., 2003). They also exhibit biological effects (Takechi et al., 2004) such as growth inhibition of Escherichia coli and cyclooxygenase inhibitory activity (Singh et al., 2004).

In the title molecule (I), Fig. 1, the heterocyclic ring adopts a screw-boat conformation, with all substituents equatorial. The phenyl ring at position 3 forms dihedral angles of 78.12 (15)° and 72.67 (15)° with the phenyl rings at positions 5 and 6, respectively. The dihedral angle between the phenyl rings at positions 5 and 6 is 67.32 (14)°. The most prominent intermolecular interaction in the crystal structure is a C65—H65···π contact involving the C31–C36 phenyl ring (Table 1).

Related literature top

Some 2-alkyl-3,5,6-triphenyl-2,3-dihydropyrazines have been reported to exhibit fluorescence in the solid-state, see: Baliah & Pandiarajan (1978). For the use of dihydropyrazines in medicine, in particular with reference to DNA breakage activity, see: Yamaguchi et al. (2003). For their biological activity, see: Singh et al. (2004) and their cyclooxygenase inhibitory activity, see: Takechi et al. (2004).

Experimental top

To a homogeneous solution of benzil (1.05 g, 0.005 mol) and 1-methyl-2-phenyl-1,2-ethanediamine dihydrochloride (1.11 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 333–353 K (4:1 v/v) gave the pure product in 1.72 g (80%) yield. .

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SIR2004 (Burla et al., 2005); 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 (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.

2-Methyl-3,5,6-triphenyl-2,3-dihydropyrazine top

Crystal data top

C₂₃H₂₀N₂	Z = 2
M_r = 324.41	F(000) = 344
Triclinic, P1	D_x = 1.156 Mg m⁻³
Hall symbol: -P 1	Melting point: 460 K
a = 10.4406 (10) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.5753 (7) Å	Cell parameters from 5680 reflections
c = 11.0810 (13) Å	θ = 5.2–77.4°
α = 93.439 (8)°	µ = 0.52 mm⁻¹
β = 114.161 (10)°	T = 295 K
γ = 118.343 (9)°	Prism, pale yellow
V = 931.9 (2) Å³	0.41 × 0.36 × 0.28 mm

Data collection top

Oxford Diffraction Gemini R diffractometer	3852 independent reflections
Radiation source: fine-focus sealed tube	3195 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 10.5081 pixels mm^-1	θ_max = 77.5°, θ_min = 5.2°
ϕ and ω scans	h = −13→13
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = −13→10
T_min = 0.831, T_max = 0.885	l = −13→13
8513 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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.270	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1784P)² + 0.1376P] where P = (F_o² + 2F_c²)/3
3852 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₃H₂₀N₂	γ = 118.343 (9)°
M_r = 324.41	V = 931.9 (2) Å³
Triclinic, P1	Z = 2
a = 10.4406 (10) Å	Cu Kα radiation
b = 10.5753 (7) Å	µ = 0.52 mm⁻¹
c = 11.0810 (13) Å	T = 295 K
α = 93.439 (8)°	0.41 × 0.36 × 0.28 mm
β = 114.161 (10)°

Data collection top

Oxford Diffraction Gemini R diffractometer	3852 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	3195 reflections with I > 2σ(I)
T_min = 0.831, T_max = 0.885	R_int = 0.045
8513 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.086	0 restraints
wR(F²) = 0.270	H-atom parameters constrained
S = 1.09	Δρ_max = 0.47 e Å⁻³
3852 reflections	Δρ_min = −0.27 e Å⁻³
227 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
N1	0.0780 (2)	0.1850 (2)	−0.0471 (2)	0.0633 (6)
N4	0.39318 (19)	0.25469 (17)	−0.01087 (17)	0.0512 (5)
C2	0.0900 (3)	0.0714 (2)	−0.1158 (3)	0.0613 (7)
C3	0.2375 (3)	0.1513 (2)	−0.1432 (2)	0.0551 (6)
C5	0.3812 (2)	0.3247 (2)	0.0777 (2)	0.0491 (5)
C6	0.2163 (2)	0.3057 (2)	0.0441 (2)	0.0536 (6)
C21	−0.0774 (3)	−0.0383 (3)	−0.2471 (3)	0.0824 (9)
C31	0.2605 (3)	0.0442 (2)	−0.2156 (2)	0.0587 (6)
C32	0.3089 (3)	−0.0438 (3)	−0.1466 (3)	0.0712 (8)
C33	0.3318 (4)	−0.1415 (3)	−0.2108 (3)	0.0873 (10)
C34	0.3090 (4)	−0.1517 (3)	−0.3418 (3)	0.0930 (10)
C35	0.2604 (4)	−0.0662 (4)	−0.4115 (3)	0.0901 (10)
C36	0.2364 (3)	0.0324 (3)	−0.3491 (3)	0.0732 (8)
C51	0.5327 (2)	0.4176 (2)	0.2180 (2)	0.0498 (6)
C52	0.5222 (3)	0.4188 (3)	0.3387 (3)	0.0634 (7)
C53	0.6663 (3)	0.4975 (3)	0.4688 (3)	0.0739 (9)
C54	0.8218 (3)	0.5780 (3)	0.4792 (3)	0.0725 (8)
C55	0.8337 (3)	0.5780 (3)	0.3593 (3)	0.0658 (7)
C56	0.6909 (2)	0.4972 (2)	0.2294 (2)	0.0539 (6)
C61	0.2079 (3)	0.4259 (2)	0.1105 (2)	0.0537 (6)
C62	0.0694 (3)	0.3844 (3)	0.1264 (3)	0.0638 (7)
C63	0.0531 (3)	0.4931 (3)	0.1805 (3)	0.0762 (10)
C64	0.1712 (4)	0.6439 (3)	0.2153 (3)	0.0806 (10)
C65	0.3098 (3)	0.6872 (3)	0.1991 (3)	0.0750 (9)
C66	0.3283 (3)	0.5782 (3)	0.1468 (3)	0.0630 (7)
H2	0.11272	0.01451	−0.05249	0.0736*
H3	0.21696	0.21204	−0.20281	0.0661*
H21A	−0.16525	−0.07906	−0.22411	0.1236*
H21B	−0.07434	−0.11930	−0.28702	0.1236*
H21C	−0.09824	0.01403	−0.31308	0.1236*
H32	0.32603	−0.03712	−0.05663	0.0854*
H33	0.36313	−0.20078	−0.16377	0.1046*
H34	0.32629	−0.21646	−0.38372	0.1115*
H35	0.24329	−0.07406	−0.50159	0.1078*
H36	0.20407	0.09047	−0.39721	0.0879*
H52	0.41748	0.36626	0.33246	0.0761*
H53	0.65783	0.49590	0.54911	0.0886*
H54	0.91824	0.63205	0.56637	0.0869*
H55	0.93864	0.63279	0.36618	0.0790*
H56	0.70022	0.49594	0.14949	0.0647*
H62	−0.01299	0.28242	0.10022	0.0765*
H63	−0.03835	0.46414	0.19338	0.0914*
H64	0.15848	0.71699	0.24976	0.0967*
H65	0.39029	0.78941	0.22342	0.0900*
H66	0.42124	0.60729	0.13614	0.0757*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0477 (9)	0.0567 (10)	0.0707 (12)	0.0264 (8)	0.0224 (8)	0.0037 (8)
N4	0.0459 (8)	0.0449 (8)	0.0534 (9)	0.0233 (7)	0.0207 (7)	0.0036 (6)
C2	0.0515 (11)	0.0536 (11)	0.0620 (12)	0.0248 (9)	0.0216 (9)	0.0032 (9)
C3	0.0529 (10)	0.0477 (10)	0.0524 (11)	0.0283 (8)	0.0171 (9)	0.0030 (8)
C5	0.0431 (9)	0.0440 (9)	0.0542 (10)	0.0234 (7)	0.0211 (8)	0.0071 (7)
C6	0.0453 (9)	0.0514 (10)	0.0587 (11)	0.0266 (8)	0.0229 (8)	0.0072 (8)
C21	0.0577 (13)	0.0709 (15)	0.0799 (17)	0.0244 (11)	0.0199 (12)	−0.0044 (12)
C31	0.0504 (10)	0.0485 (10)	0.0551 (11)	0.0260 (8)	0.0127 (8)	−0.0046 (8)
C32	0.0698 (14)	0.0611 (12)	0.0694 (14)	0.0411 (11)	0.0196 (11)	0.0067 (10)
C33	0.0798 (17)	0.0651 (14)	0.092 (2)	0.0482 (13)	0.0160 (14)	−0.0018 (13)
C34	0.0795 (17)	0.0765 (17)	0.093 (2)	0.0488 (14)	0.0179 (15)	−0.0205 (15)
C35	0.0881 (19)	0.094 (2)	0.0633 (15)	0.0484 (16)	0.0244 (14)	−0.0110 (14)
C36	0.0730 (14)	0.0702 (14)	0.0593 (13)	0.0419 (12)	0.0185 (11)	0.0014 (10)
C51	0.0462 (9)	0.0463 (9)	0.0546 (11)	0.0275 (8)	0.0221 (8)	0.0048 (7)
C52	0.0570 (11)	0.0717 (13)	0.0623 (12)	0.0368 (10)	0.0303 (10)	0.0081 (10)
C53	0.0755 (15)	0.0947 (17)	0.0516 (12)	0.0510 (14)	0.0290 (11)	0.0056 (11)
C54	0.0594 (12)	0.0782 (15)	0.0551 (12)	0.0384 (11)	0.0115 (10)	−0.0064 (10)
C55	0.0464 (10)	0.0626 (12)	0.0670 (13)	0.0249 (9)	0.0197 (10)	−0.0003 (10)
C56	0.0481 (10)	0.0512 (10)	0.0552 (11)	0.0256 (8)	0.0233 (8)	0.0057 (8)
C61	0.0484 (10)	0.0577 (10)	0.0552 (11)	0.0330 (9)	0.0224 (8)	0.0101 (8)
C62	0.0544 (11)	0.0722 (13)	0.0677 (13)	0.0380 (10)	0.0296 (10)	0.0164 (10)
C63	0.0703 (14)	0.1005 (19)	0.0767 (16)	0.0583 (15)	0.0393 (12)	0.0184 (14)
C64	0.0844 (17)	0.0880 (17)	0.0815 (17)	0.0620 (15)	0.0363 (14)	0.0059 (13)
C65	0.0728 (14)	0.0619 (13)	0.0844 (17)	0.0404 (12)	0.0326 (13)	0.0053 (11)
C66	0.0554 (11)	0.0586 (12)	0.0741 (14)	0.0331 (10)	0.0309 (10)	0.0084 (10)

Geometric parameters (Å, º) top

N1—C2	1.466 (4)	C62—C63	1.377 (5)
N1—C6	1.279 (3)	C63—C64	1.372 (4)
N4—C3	1.469 (3)	C64—C65	1.389 (6)
N4—C5	1.276 (3)	C65—C66	1.387 (5)
C2—C3	1.535 (4)	C2—H2	0.9800
C2—C21	1.519 (4)	C3—H3	0.9800
C3—C31	1.514 (4)	C21—H21A	0.9600
C5—C6	1.510 (3)	C21—H21B	0.9600
C5—C51	1.487 (3)	C21—H21C	0.9600
C6—C61	1.487 (3)	C32—H32	0.9300
C31—C32	1.386 (4)	C33—H33	0.9300
C31—C36	1.382 (4)	C34—H34	0.9300
C32—C33	1.384 (5)	C35—H35	0.9300
C33—C34	1.360 (4)	C36—H36	0.9300
C34—C35	1.368 (5)	C52—H52	0.9300
C35—C36	1.390 (5)	C53—H53	0.9300
C51—C52	1.386 (4)	C54—H54	0.9300
C51—C56	1.396 (3)	C55—H55	0.9300
C52—C53	1.388 (4)	C56—H56	0.9300
C53—C54	1.377 (5)	C62—H62	0.9300
C54—C55	1.384 (4)	C63—H63	0.9300
C55—C56	1.382 (4)	C64—H64	0.9300
C61—C62	1.389 (5)	C65—H65	0.9300
C61—C66	1.386 (4)	C66—H66	0.9300

N1···N4	2.848 (3)	H2···C5	2.8400
N4···N1	2.848 (3)	H2···C32	2.9200
N1···H62	2.5700	H2···H32	2.5500
N1···H2ⁱ	2.7800	H2···N1ⁱ	2.7800
N4···H32	2.7800	H3···C6	2.8600
N4···H56	2.6400	H3···H21C	2.5600
N4···H33ⁱⁱ	2.8300	H3···H36	2.3600
N4···H66ⁱⁱⁱ	2.7500	H3···C55ⁱⁱⁱ	3.0100
C32···C32ⁱⁱ	3.585 (5)	H3···C56ⁱⁱⁱ	2.8300
C51···C66	3.207 (4)	H21B···C31	2.7700
C52···C66	3.407 (5)	H21C···H3	2.5600
C52···C61	3.261 (4)	H21C···C35^v	3.0600
C61···C52	3.261 (4)	H21C···H35^v	2.3300
C62···C64^iv	3.479 (4)	H32···N4	2.7800
C64···C62^iv	3.479 (4)	H32···C2	3.0500
C66···C51	3.207 (4)	H32···H2	2.5500
C66···C52	3.407 (5)	H32···C33ⁱⁱ	3.0600
C2···H32	3.0500	H33···N4ⁱⁱ	2.8300
C5···H2	2.8400	H33···C51ⁱⁱ	3.0900
C5···H66	2.8100	H33···C56ⁱⁱ	2.9000
C6···H52	2.8300	H35···H21C^v	2.3300
C6···H3	2.8600	H36···H3	2.3600
C31···H21B	2.7700	H52···C6	2.8300
C32···H2	2.9200	H52···C61	2.8900
C33···H32ⁱⁱ	3.0600	H52···H53^vi	2.4800
C35···H65ⁱⁱⁱ	3.0200	H53···C52^vi	3.0500
C35···H21C^v	3.0600	H53···H52^vi	2.4800
C36···H65ⁱⁱⁱ	2.9900	H56···N4	2.6400
C51···H66	2.7900	H62···N1	2.5700
C51···H33ⁱⁱ	3.0900	H65···C35ⁱⁱⁱ	3.0200
C52···H53^vi	3.0500	H65···C36ⁱⁱⁱ	2.9900
C55···H3ⁱⁱⁱ	3.0100	H66···C5	2.8100
C56···H33ⁱⁱ	2.9000	H66···C51	2.7900
C56···H3ⁱⁱⁱ	2.8300	H66···N4ⁱⁱⁱ	2.7500
C61···H52	2.8900

C2—N1—C6	116.8 (2)	C21—C2—H2	108.00
C3—N4—C5	116.3 (2)	N4—C3—H3	108.00
N1—C2—C3	109.45 (18)	C2—C3—H3	108.00
N1—C2—C21	109.0 (3)	C31—C3—H3	108.00
C3—C2—C21	113.5 (2)	C2—C21—H21A	109.00
N4—C3—C2	109.53 (19)	C2—C21—H21B	109.00
N4—C3—C31	109.3 (2)	C2—C21—H21C	109.00
C2—C3—C31	113.97 (18)	H21A—C21—H21B	109.00
N4—C5—C6	121.10 (19)	H21A—C21—H21C	110.00
N4—C5—C51	117.5 (2)	H21B—C21—H21C	109.00
C6—C5—C51	121.34 (19)	C31—C32—H32	120.00
N1—C6—C5	120.0 (2)	C33—C32—H32	120.00
N1—C6—C61	117.9 (2)	C32—C33—H33	120.00
C5—C6—C61	122.14 (19)	C34—C33—H33	120.00
C3—C31—C32	119.6 (2)	C33—C34—H34	120.00
C3—C31—C36	121.8 (2)	C35—C34—H34	120.00
C32—C31—C36	118.5 (3)	C34—C35—H35	120.00
C31—C32—C33	120.4 (3)	C36—C35—H35	120.00
C32—C33—C34	120.7 (3)	C31—C36—H36	120.00
C33—C34—C35	119.6 (4)	C35—C36—H36	120.00
C34—C35—C36	120.7 (3)	C51—C52—H52	120.00
C31—C36—C35	120.1 (3)	C53—C52—H52	120.00
C5—C51—C52	121.7 (2)	C52—C53—H53	120.00
C5—C51—C56	119.25 (19)	C54—C53—H53	120.00
C52—C51—C56	118.9 (2)	C53—C54—H54	120.00
C51—C52—C53	120.7 (3)	C55—C54—H54	120.00
C52—C53—C54	120.1 (3)	C54—C55—H55	120.00
C53—C54—C55	119.7 (3)	C56—C55—H55	120.00
C54—C55—C56	120.5 (3)	C51—C56—H56	120.00
C51—C56—C55	120.1 (2)	C55—C56—H56	120.00
C6—C61—C62	119.0 (2)	C61—C62—H62	120.00
C6—C61—C66	121.5 (3)	C63—C62—H62	120.00
C62—C61—C66	119.4 (3)	C62—C63—H63	120.00
C61—C62—C63	120.5 (3)	C64—C63—H63	120.00
C62—C63—C64	120.2 (4)	C63—C64—H64	120.00
C63—C64—C65	119.9 (3)	C65—C64—H64	120.00
C64—C65—C66	120.1 (3)	C64—C65—H65	120.00
C61—C66—C65	119.8 (3)	C66—C65—H65	120.00
N1—C2—H2	108.00	C61—C66—H66	120.00
C3—C2—H2	108.00	C65—C66—H66	120.00

C6—N1—C2—C3	−38.6 (3)	C5—C6—C61—C62	−151.9 (2)
C6—N1—C2—C21	−163.2 (2)	C5—C6—C61—C66	33.1 (3)
C2—N1—C6—C5	−0.8 (3)	C3—C31—C32—C33	−179.5 (3)
C2—N1—C6—C61	177.16 (19)	C36—C31—C32—C33	−0.2 (5)
C5—N4—C3—C2	−37.2 (3)	C3—C31—C36—C35	179.4 (3)
C5—N4—C3—C31	−162.71 (18)	C32—C31—C36—C35	0.1 (5)
C3—N4—C5—C6	−2.4 (3)	C31—C32—C33—C34	0.7 (5)
C3—N4—C5—C51	173.76 (17)	C32—C33—C34—C35	−1.0 (6)
N1—C2—C3—N4	57.9 (3)	C33—C34—C35—C36	0.9 (6)
N1—C2—C3—C31	−179.37 (19)	C34—C35—C36—C31	−0.4 (6)
C21—C2—C3—N4	179.9 (2)	C5—C51—C52—C53	175.2 (3)
C21—C2—C3—C31	−57.3 (3)	C56—C51—C52—C53	−0.1 (4)
N4—C3—C31—C32	56.1 (3)	C5—C51—C56—C55	−176.7 (2)
N4—C3—C31—C36	−123.2 (3)	C52—C51—C56—C55	−1.3 (4)
C2—C3—C31—C32	−66.8 (3)	C51—C52—C53—C54	1.3 (5)
C2—C3—C31—C36	113.9 (3)	C52—C53—C54—C55	−1.0 (5)
N4—C5—C6—N1	25.0 (3)	C53—C54—C55—C56	−0.4 (5)
N4—C5—C6—C61	−152.88 (19)	C54—C55—C56—C51	1.6 (4)
C51—C5—C6—N1	−151.0 (2)	C6—C61—C62—C63	−176.5 (2)
C51—C5—C6—C61	31.1 (3)	C66—C61—C62—C63	−1.4 (4)
N4—C5—C51—C52	−138.4 (2)	C6—C61—C66—C65	175.3 (2)
N4—C5—C51—C56	36.9 (3)	C62—C61—C66—C65	0.3 (4)
C6—C5—C51—C52	37.7 (3)	C61—C62—C63—C64	2.0 (4)
C6—C5—C51—C56	−147.0 (2)	C62—C63—C64—C65	−1.6 (4)
N1—C6—C61—C62	30.2 (3)	C63—C64—C65—C66	0.5 (4)
N1—C6—C61—C66	−144.8 (2)	C64—C65—C66—C61	0.1 (4)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z; (iii) −x+1, −y+1, −z; (iv) −x, −y+1, −z; (v) −x, −y, −z−1; (vi) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C65—H65···Cg(C31–C36)ⁱⁱⁱ	0.93	2.97	3.834 (3)	156

Symmetry code: (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₂
M_r	324.41
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	10.4406 (10), 10.5753 (7), 11.0810 (13)
α, β, γ (°)	93.439 (8), 114.161 (10), 118.343 (9)
V (Å³)	931.9 (2)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.41 × 0.36 × 0.28

Data collection
Diffractometer	Oxford Diffraction Gemini R diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.831, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	8513, 3852, 3195
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.086, 0.270, 1.09
No. of reflections	3852
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.27

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C65—H65···Cg(C31–C36)ⁱ	0.93	2.97	3.834 (3)	156

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06 (UGC-SERO), Link No. 2355, 10/01/2007]. RJB acknowledges the NSF MRI programme (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Baliah, V. & Pandiarajan, K. (1978). Indian J. Chem. Sect. B, 16, 73–74. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, S. K., Saibaba, V., Ravikumar, V., Rudrawar, S., Daga, P., Rao, C. S., Akhila, V., Hegde, P. & Rao, Y. K. (2004). Bioorg. Med. Chem. 12, 1881–1893. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takechi, S., Yamaguchi, T., Nomura, H., Minematsu, T. & Nakayama, T. (2004). Mutat. Res. 560, 49–55. Web of Science CrossRef PubMed CAS Google Scholar
Yamaguchi, T., Nomura, H., Matsunaga, K., Ito, S., Tokata, J. & Karube, Y. (2003). Biol. Pharm. Bull. 26, 1523–1527. Web of Science CrossRef PubMed CAS Google Scholar