2,3,5-Triphenyl­pyrazine

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

doi:10.1107/S1600536808041627

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o106

doi:10.1107/S1600536808041627

Open

access

2,3,5-Triphenylpyrazine

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

^aPG 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 2 December 2008; accepted 8 December 2008; online 13 December 2008)

In the title molecule, C₂₂H₁₆N₂, the pyrazine ring deviates very slightly from planarity [maximum deviation 0.044 (3) Å], tending towards a twist-boat conformation. The phenyl ring at position 3 makes dihedral angles of 64.0 (2) and 45.8 (2)°, respectively, with the phenyl rings at positions 2 and 5. The dihedral angle between the phenyl rings at positions 2 and 5 is 49.7 (2)°. A C—H⋯π interaction is found in the crystal structure, but no classical hydrogen bonds form.

Related literature

For the biological properties of pyrazines, see: Foks et al. (2004 ); Premkumar & Govindarajan (2005 ); Sondhi et al. (2005 ).

Experimental

Crystal data

C₂₂H₁₆N₂
M_r = 308.37
Orthorhombic, P n a 2₁
a = 15.563 (2) Å
b = 6.2005 (9) Å
c = 16.845 (3) Å
V = 1625.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 (2) K
0.44 × 0.35 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.968, T_max = 0.985
17890 measured reflections
1730 independent reflections
1109 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.129
S = 1.02
1730 reflections
218 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C53—H53⋯Cgⁱ	0.93	2.98	3.909 (5)	174
Symmetry code: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z]$ . Cg is the centroid of the C21–C26 phenyl ring.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-NT (Bruker, 2004); data reduction: SAINT-NT; 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041627/wn2297sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041627/wn2297Isup2.hkl

checkCIF report

Comment top

Pyrazines are heterocycles which exhibit nutty, roasted or earth flavouring agents. 2-Cyanopyrazine derivatives show anticancer, anti-inflammatory and analgesic activities (Sondhi et al., 2005). Pyrazine derivatives exhibit tuberculostatic activity (Foks et al., 2004) and antimicrobial activity (Premkumar & Govindarajan, 2005).

In the title molecule, C₂₂H₁₆N₂, (Fig. 1), the pyrazine ring deviates very slightly from planarity, tending towards a twist-boat conformation. The phenyl ring at position 3 makes dihedral angles of 64.0 (2)° and 45.8 (2)° with the phenyl rings at positions 2 and 5, respectively. The dihedral angle between the phenyl rings at positions 2 and 5 is 49.7 (2)°. A C53—H53···π interaction involving the phenyl (C21–C26) ring at position 2 is found in the crystal structure, but no classical hydrogen bonds.

Related literature top

For the biological properties of pyrazines, see: Foks et al. (2004); Premkumar & Govindarajan (2005); Sondhi et al. (2005). Cg is the centroid of the C21–C26 phenyl ring.

Experimental top

To a homogeneous solution of benzil (1.05 g, 0.005 mol) and 1-phenylethanediamine dihydrochloride (1.04 g, 0.005 mol) in ethanol, 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 off and purified by column chromatography on silica gel. Elution with benzene: petroleum ether (4:1 v/v) at 333–353 K gave the product in pure form. Yield 1.6 g (80%).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-NT (Bruker, 2004); data reduction: SAINT-NT (Bruker, 2004); 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, 2003).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

2,3,5-Triphenylpyrazine top

Crystal data top

C₂₂H₁₆N₂	D_x = 1.260 Mg m⁻³
M_r = 308.37	Melting point: 421 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2955 reflections
a = 15.563 (2) Å	θ = 2.4–21.2°
b = 6.2005 (9) Å	µ = 0.07 mm⁻¹
c = 16.845 (3) Å	T = 296 K
V = 1625.5 (4) Å³	Chunk, colourless
Z = 4	0.44 × 0.35 × 0.21 mm
F(000) = 648

Data collection top

Bruker APEXII CCD diffractometer	1730 independent reflections
Radiation source: fine-focus sealed tube	1109 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
ϕ and ω scans	θ_max = 26.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −19→19
T_min = 0.968, T_max = 0.985	k = −7→7
17890 measured reflections	l = −20→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0653P)² + 0.1081P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
1730 reflections	Δρ_max = 0.13 e Å⁻³
218 parameters	Δρ_min = −0.13 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)

Crystal data top

C₂₂H₁₆N₂	V = 1625.5 (4) Å³
M_r = 308.37	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 15.563 (2) Å	µ = 0.07 mm⁻¹
b = 6.2005 (9) Å	T = 296 K
c = 16.845 (3) Å	0.44 × 0.35 × 0.21 mm

Data collection top

Bruker APEXII CCD diffractometer	1730 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1109 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.985	R_int = 0.091
17890 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.129	H-atom parameters constrained
S = 1.02	Δρ_max = 0.13 e Å⁻³
1730 reflections	Δρ_min = −0.13 e Å⁻³
218 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	0.2355 (2)	0.1296 (5)	0.19242 (19)	0.0547 (12)
N4	0.3436 (2)	−0.1252 (5)	0.10173 (19)	0.0487 (11)
C2	0.2412 (3)	0.1612 (5)	0.1141 (2)	0.0463 (12)
C3	0.3009 (3)	0.0395 (6)	0.0686 (2)	0.0447 (12)
C5	0.3329 (3)	−0.1640 (6)	0.1791 (2)	0.0477 (12)
C6	0.2822 (3)	−0.0252 (7)	0.2244 (3)	0.0557 (14)
C21	0.1810 (3)	0.3188 (6)	0.0793 (2)	0.0480 (12)
C22	0.1658 (3)	0.5110 (6)	0.1192 (3)	0.0547 (16)
C23	0.1074 (3)	0.6577 (7)	0.0897 (3)	0.0670 (17)
C24	0.0622 (3)	0.6125 (8)	0.0212 (3)	0.0717 (17)
C25	0.0760 (3)	0.4218 (8)	−0.0185 (3)	0.0683 (19)
C26	0.1359 (3)	0.2775 (8)	0.0110 (3)	0.0610 (17)
C31	0.3243 (3)	0.0908 (7)	−0.0142 (2)	0.0500 (14)
C32	0.3486 (3)	0.2977 (7)	−0.0358 (3)	0.0583 (16)
C33	0.3772 (3)	0.3414 (7)	−0.1116 (3)	0.0653 (17)
C34	0.3783 (3)	0.1810 (8)	−0.1676 (3)	0.0660 (17)
C35	0.3525 (3)	−0.0229 (8)	−0.1474 (3)	0.0687 (17)
C36	0.3261 (3)	−0.0692 (6)	−0.0714 (2)	0.0577 (16)
C51	0.3770 (3)	−0.3528 (6)	0.2136 (2)	0.0483 (12)
C52	0.4302 (3)	−0.4792 (7)	0.1662 (3)	0.0610 (17)
C53	0.4682 (3)	−0.6620 (7)	0.1961 (3)	0.0730 (19)
C54	0.4543 (3)	−0.7247 (8)	0.2734 (3)	0.0747 (19)
C55	0.4017 (4)	−0.6012 (8)	0.3210 (3)	0.0770 (19)
C56	0.3635 (3)	−0.4195 (7)	0.2911 (3)	0.0667 (17)
H6	0.28114	−0.04259	0.27921	0.0669*
H22	0.19510	0.54089	0.16601	0.0653*
H23	0.09840	0.78757	0.11605	0.0803*
H24	0.02234	0.71109	0.00186	0.0859*
H25	0.04549	0.39011	−0.06447	0.0819*
H26	0.14584	0.14928	−0.01612	0.0727*
H32	0.34552	0.40842	0.00137	0.0699*
H33	0.39584	0.47943	−0.12464	0.0783*
H34	0.39640	0.21058	−0.21902	0.0788*
H35	0.35281	−0.13135	−0.18555	0.0820*
H36	0.30936	−0.20876	−0.05833	0.0693*
H52	0.44015	−0.43949	0.11371	0.0731*
H53	0.50365	−0.74446	0.16366	0.0872*
H54	0.48007	−0.84883	0.29325	0.0894*
H55	0.39220	−0.64112	0.37352	0.0927*
H56	0.32749	−0.33888	0.32367	0.0800*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.062 (2)	0.052 (2)	0.050 (2)	0.0055 (17)	0.0027 (16)	−0.0004 (16)
N4	0.0533 (19)	0.0458 (18)	0.047 (2)	0.0009 (15)	0.0024 (15)	0.0030 (15)
C2	0.057 (2)	0.042 (2)	0.040 (2)	−0.0052 (18)	0.0015 (17)	−0.0036 (18)
C3	0.055 (2)	0.039 (2)	0.040 (2)	0.0020 (18)	0.0004 (16)	−0.0025 (16)
C5	0.055 (2)	0.047 (2)	0.041 (2)	−0.0069 (18)	−0.0003 (17)	0.0022 (18)
C6	0.069 (3)	0.057 (2)	0.041 (2)	−0.002 (2)	−0.0020 (19)	−0.001 (2)
C21	0.051 (2)	0.047 (2)	0.046 (2)	−0.0008 (17)	0.0017 (18)	−0.0008 (18)
C22	0.060 (3)	0.050 (2)	0.054 (3)	0.000 (2)	0.0030 (19)	−0.0013 (19)
C23	0.067 (3)	0.055 (3)	0.079 (3)	0.011 (2)	0.007 (3)	0.001 (2)
C24	0.066 (3)	0.077 (3)	0.072 (3)	0.013 (3)	0.002 (3)	0.008 (3)
C25	0.067 (3)	0.085 (4)	0.053 (3)	0.012 (3)	−0.006 (2)	0.004 (2)
C26	0.067 (3)	0.062 (3)	0.054 (3)	0.002 (2)	−0.004 (2)	−0.002 (2)
C31	0.054 (2)	0.054 (3)	0.042 (2)	0.0078 (19)	−0.0010 (18)	0.0036 (18)
C32	0.077 (3)	0.047 (2)	0.051 (3)	0.003 (2)	0.009 (2)	0.002 (2)
C33	0.077 (3)	0.056 (3)	0.063 (3)	0.006 (2)	0.012 (2)	0.015 (2)
C34	0.076 (3)	0.076 (3)	0.046 (3)	0.015 (3)	0.009 (2)	0.014 (3)
C35	0.089 (3)	0.070 (3)	0.047 (3)	0.017 (3)	0.001 (2)	−0.006 (2)
C36	0.079 (3)	0.046 (2)	0.048 (3)	0.009 (2)	0.001 (2)	−0.004 (2)
C51	0.049 (2)	0.045 (2)	0.051 (2)	−0.0034 (18)	−0.0025 (18)	0.0050 (19)
C52	0.064 (3)	0.056 (3)	0.063 (3)	−0.001 (2)	0.005 (2)	0.013 (2)
C53	0.066 (3)	0.061 (3)	0.092 (4)	0.012 (2)	0.008 (3)	0.011 (3)
C54	0.075 (3)	0.056 (3)	0.093 (4)	0.007 (3)	−0.019 (3)	0.019 (3)
C55	0.098 (4)	0.072 (3)	0.061 (3)	0.010 (3)	−0.013 (3)	0.012 (3)
C56	0.085 (3)	0.064 (3)	0.051 (3)	0.013 (2)	−0.010 (2)	0.006 (2)

Geometric parameters (Å, º) top

N1—C2	1.337 (5)	C51—C56	1.386 (6)
N1—C6	1.319 (6)	C52—C53	1.374 (6)
N4—C3	1.340 (5)	C53—C54	1.376 (7)
N4—C5	1.336 (5)	C54—C55	1.378 (7)
C2—C3	1.421 (6)	C55—C56	1.370 (7)
C2—C21	1.475 (6)	C6—H6	0.9300
C3—C31	1.476 (5)	C22—H22	0.9300
C5—C6	1.395 (6)	C23—H23	0.9300
C5—C51	1.476 (6)	C24—H24	0.9300
C21—C22	1.389 (6)	C25—H25	0.9300
C21—C26	1.372 (6)	C26—H26	0.9300
C22—C23	1.379 (6)	C32—H32	0.9300
C23—C24	1.380 (7)	C33—H33	0.9300
C24—C25	1.375 (7)	C34—H34	0.9300
C25—C26	1.384 (7)	C35—H35	0.9300
C31—C32	1.386 (6)	C36—H36	0.9300
C31—C36	1.383 (5)	C52—H52	0.9300
C32—C33	1.379 (7)	C53—H53	0.9300
C33—C34	1.371 (7)	C54—H54	0.9300
C34—C35	1.370 (7)	C55—H55	0.9300
C35—C36	1.375 (6)	C56—H56	0.9300
C51—C52	1.392 (6)

N1···N4	2.768 (4)	C34···H54^viii	3.0900
N4···N1	2.768 (4)	C35···H54^viii	2.9000
N1···H22	2.6600	C35···H56^v	3.0600
N1···H35ⁱ	2.8800	C51···H22ⁱⁱ	3.0200
N4···H36	2.8000	C52···H23^vii	3.0000
N4···H52	2.4700	C56···H6	2.6700
C5···C22ⁱⁱ	3.441 (6)	H6···C56	2.6700
C6···C34ⁱⁱⁱ	3.587 (7)	H6···H56	2.1100
C6···C54^iv	3.366 (7)	H22···N1	2.6600
C21···C32	3.253 (6)	H22···C5^iv	2.8300
C22···C5^iv	3.441 (6)	H22···C51^iv	3.0200
C26···C32	3.405 (7)	H23···C52^ix	3.0000
C26···C31	3.181 (7)	H25···C33^ix	3.0900
C31···C26	3.181 (7)	H26···C3	2.8900
C32···C26	3.405 (7)	H26···C31	2.8000
C32···C21	3.253 (6)	H32···C2	2.9300
C34···C6^v	3.587 (7)	H32···C21	2.9300
C35···C56^v	3.576 (7)	H32···H52^iv	2.5800
C54···C6ⁱⁱ	3.366 (7)	H35···N1^x	2.8800
C56···C35ⁱⁱⁱ	3.576 (7)	H36···N4	2.8000
C2···H32	2.9300	H52···N4	2.4700
C3···H26	2.8900	H52···H32ⁱⁱ	2.5800
C5···H22ⁱⁱ	2.8300	H54···C34^xi	3.0900
C6···H56	2.6600	H54···C35^xi	2.9000
C21···H32	2.9300	H55···C24^xii	3.0000
C24···H55^vi	3.0000	H56···C6	2.6600
C31···H26	2.8000	H56···H6	2.1100
C33···H25^vii	3.0900	H56···C35ⁱⁱⁱ	3.0600

C2—N1—C6	118.2 (4)	C54—C55—C56	120.1 (5)
C3—N4—C5	118.8 (3)	C51—C56—C55	121.8 (4)
N1—C2—C3	119.9 (3)	N1—C6—H6	119.00
N1—C2—C21	116.6 (3)	C5—C6—H6	119.00
C3—C2—C21	123.5 (3)	C21—C22—H22	120.00
N4—C3—C2	120.3 (3)	C23—C22—H22	120.00
N4—C3—C31	115.8 (4)	C22—C23—H23	120.00
C2—C3—C31	123.8 (3)	C24—C23—H23	120.00
N4—C5—C6	119.6 (4)	C23—C24—H24	120.00
N4—C5—C51	118.0 (3)	C25—C24—H24	120.00
C6—C5—C51	122.5 (3)	C24—C25—H25	120.00
N1—C6—C5	122.5 (4)	C26—C25—H25	120.00
C2—C21—C22	119.0 (3)	C21—C26—H26	119.00
C2—C21—C26	122.3 (4)	C25—C26—H26	119.00
C22—C21—C26	118.6 (4)	C31—C32—H32	119.00
C21—C22—C23	120.3 (4)	C33—C32—H32	120.00
C22—C23—C24	120.2 (4)	C32—C33—H33	120.00
C23—C24—C25	120.1 (4)	C34—C33—H33	120.00
C24—C25—C26	119.1 (5)	C33—C34—H34	120.00
C21—C26—C25	121.7 (4)	C35—C34—H34	120.00
C3—C31—C32	121.0 (4)	C34—C35—H35	120.00
C3—C31—C36	120.6 (4)	C36—C35—H35	120.00
C32—C31—C36	118.4 (4)	C31—C36—H36	120.00
C31—C32—C33	120.9 (4)	C35—C36—H36	120.00
C32—C33—C34	119.9 (4)	C51—C52—H52	120.00
C33—C34—C35	119.7 (5)	C53—C52—H52	120.00
C34—C35—C36	120.8 (4)	C52—C53—H53	120.00
C31—C36—C35	120.3 (4)	C54—C53—H53	120.00
C5—C51—C52	119.8 (3)	C53—C54—H54	120.00
C5—C51—C56	122.5 (4)	C55—C54—H54	120.00
C52—C51—C56	117.6 (4)	C54—C55—H55	120.00
C51—C52—C53	120.7 (4)	C56—C55—H55	120.00
C52—C53—C54	120.8 (4)	C51—C56—H56	119.00
C53—C54—C55	119.1 (5)	C55—C56—H56	119.00

C6—N1—C2—C3	−4.3 (6)	C2—C21—C22—C23	−177.5 (4)
C6—N1—C2—C21	173.4 (4)	C26—C21—C22—C23	−0.9 (7)
C2—N1—C6—C5	−3.9 (6)	C2—C21—C26—C25	176.3 (4)
C5—N4—C3—C2	−4.0 (6)	C22—C21—C26—C25	−0.2 (7)
C5—N4—C3—C31	172.3 (4)	C21—C22—C23—C24	1.4 (7)
C3—N4—C5—C6	−4.0 (6)	C22—C23—C24—C25	−0.8 (7)
C3—N4—C5—C51	176.9 (4)	C23—C24—C25—C26	−0.3 (7)
N1—C2—C3—N4	8.5 (6)	C24—C25—C26—C21	0.8 (7)
N1—C2—C3—C31	−167.5 (4)	C3—C31—C32—C33	174.6 (4)
C21—C2—C3—N4	−169.0 (4)	C36—C31—C32—C33	−2.6 (7)
C21—C2—C3—C31	15.0 (6)	C3—C31—C36—C35	−176.4 (4)
N1—C2—C21—C22	42.2 (6)	C32—C31—C36—C35	0.8 (7)
N1—C2—C21—C26	−134.2 (4)	C31—C32—C33—C34	2.8 (7)
C3—C2—C21—C22	−140.2 (4)	C32—C33—C34—C35	−1.3 (7)
C3—C2—C21—C26	43.4 (6)	C33—C34—C35—C36	−0.5 (7)
N4—C3—C31—C32	−126.1 (4)	C34—C35—C36—C31	0.7 (7)
N4—C3—C31—C36	51.0 (6)	C5—C51—C52—C53	−176.5 (4)
C2—C3—C31—C32	50.0 (7)	C56—C51—C52—C53	−0.6 (7)
C2—C3—C31—C36	−132.9 (5)	C5—C51—C56—C55	176.7 (5)
N4—C5—C6—N1	8.4 (7)	C52—C51—C56—C55	0.9 (7)
C51—C5—C6—N1	−172.6 (4)	C51—C52—C53—C54	0.3 (7)
N4—C5—C51—C52	2.3 (6)	C52—C53—C54—C55	−0.2 (7)
N4—C5—C51—C56	−173.5 (4)	C53—C54—C55—C56	0.5 (8)
C6—C5—C51—C52	−176.8 (4)	C54—C55—C56—C51	−0.9 (8)
C6—C5—C51—C56	7.5 (7)

Symmetry codes: (i) −x+1/2, y+1/2, z+1/2; (ii) x, y−1, z; (iii) −x+1/2, y−1/2, z+1/2; (iv) x, y+1, z; (v) −x+1/2, y+1/2, z−1/2; (vi) −x+1/2, y+3/2, z−1/2; (vii) x+1/2, −y+1/2, z; (viii) −x+1, −y−1, z−1/2; (ix) x−1/2, −y+1/2, z; (x) −x+1/2, y−1/2, z−1/2; (xi) −x+1, −y−1, z+1/2; (xii) −x+1/2, y−3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C53—H53···Cg^xiii	0.93	2.98	3.909 (5)	174

Symmetry code: (xiii) x+1/2, −y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₂
M_r	308.37
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	15.563 (2), 6.2005 (9), 16.845 (3)
V (Å³)	1625.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.44 × 0.35 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.968, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	17890, 1730, 1109
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.129, 1.02
No. of reflections	1730
No. of parameters	218
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: APEX2 (Bruker, 2004), SAINT-NT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C53—H53···Cgⁱ	0.93	2.98	3.909 (5)	174

Symmetry code: (i) x+1/2, −y−1/2, 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 program for funding to purchase the X-ray CCD diffractometer.

References

Bruker (2004). APEX2, SAINT-NT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Foks, H., Trapkaoska, I., Janowiec, M., Zwolska, Z. & Augustynowicz-Kopec, E. (2004). Chem. Heterocycl. Cmpd, 40, 1185–1193. CrossRef CAS Google Scholar
Premkumar, T. & Govindarajan, S. (2005). World J. Microbiol. Biotechnol. 21, 479–480. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sondhi, S. M., Singh, N., Rajvanshi, S. & Johar, M. (2005). Indian J. Chem. 44B, 387–399. CAS Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar