1,2-Di-2-quinolylethene

Fun, H.-K.; Kia, R.; Maity, A.C.; Chakrabarty, R.; Goswami, S.

doi:10.1107/S160053680900186X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o354

doi:10.1107/S160053680900186X

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1,2-Di-2-quinolylethene

Hoong-Kun Fun,^a ^* Reza Kia,^a Annada C. Maity,^b Rinku Chakrabarty ^b and Shyamaprosad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 6 January 2009; accepted 15 January 2009; online 23 January 2009)

The title compound, C₂₀H₁₄N₂, comprises two crystallographically independent centrosymmetric molecules (A and B) with different conformations due to the disorder of molecule B. The whole of molecule B is disordered over two sets of positions, corresponding to a 180° rotation of the molecule, with a site-occupancy ratio of 0.780 (6):0.220 (6). The minor component of the disordered part in B has the same configuration as molecule A, but the major component is different. The dihedral angle between the planes of molecule A and molecule B (major component) is 63.22 (3)°. The crystal structure is stabilized by intermolecular C—H⋯π interactions.

Related literature

For the biological activities, molecular recognition and catalysis see, for example: Fournet et al. (2003 ); Yamada et al., (1981 ); Goswami & Mahapatra (1998 ); Goswami et al. (1989 ).

Experimental

Crystal data

C₂₀H₁₄N₂
M_r = 282.33
Monoclinic, P 2₁ /n
a = 15.6378 (2) Å
b = 6.0798 (1) Å
c = 16.0860 (2) Å
β = 108.879 (1)°
V = 1447.10 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100.0 (1) K
0.34 × 0.33 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.863, T_max = 0.993
12910 measured reflections
3317 independent reflections
2476 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.04
3317 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2A—H2AA⋯Cg1ⁱ	0.93	2.77	3.3409 (14)	121
C6A—H6AA⋯Cg2ⁱⁱ	0.93	2.65	3.5328 (18)	159
C4B—H4B⋯Cg3ⁱⁱⁱ	0.93	2.85	3.376 (12)	116
C6A—H6AA⋯Cg3^iv	0.93	2.76	3.613 (10)	152
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{3\over 2}}, -z+{\script{1\over 2}}]$ . Cg1, Cg2 and Cg3 are the centroids of the C3A–C8A, N1B/C8B/C3B/C2B/C1B/C9B and N1C/C8C/C3C/C2C/C1C/C9C rings, respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900186X/pk2144sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900186X/pk2144Isup2.hkl

checkCIF report

Comment top

Alkene or alkyne substituted quinolines are important as they exhibit significant activities against HTLV-1 transformed cells and also show the efficiency of these compounds for the treatment of ATLL (Fournet et al., 2003).

The benzylic carbon-carbon coupling reactions of benzylic halides catalyzed by Co^I(PPh₃)₃Cl and also the synthesis of diaryl ethylene have been reported (Yamada et al., 1981). The same reaction of functionalised benzylic bromides was shown to be useful for carbon-carbon bond formation by Co^I in the absence of oxygen, resulting in the convenient synthesis of a variety of functionalized benzylic dimers suitable for new spacers in molecular recognition research (Goswami & Mahapatra 1998; Goswami et al., 1989). We report here a useful and straightforward procedure for the synthesis of 1,2-di-(2-quinolyl)-ethylene from 2,2-dichloromethyl quinoline.

The title compound, Fig. 1, comprises two crystallographically independent centrosymmetric molecules with different conformations due to the disorder over two sites, corresponding to a ca180° rotation about the C9B—C10B bond. The minor component of the disordered part in B has the same configuration as molecule A, but the major component is different. The difference in conformation is that the A molecule atoms N1A-C9A-C10A-C10AA (AA is the symmetry related of A), form a chain like U shape while the corresponding atoms in the major component of B form a Z shape. The dihedral angle between the plane of molecule A and molecule B is 63.22 (3)°. In molecule B, the whole molecule is disordered over two positions with a site-occupancy factor of 0.780 (6)/0.220 (6). The crystal structure is stabilized by intermolecular C—H···π interactions (C2A—H2AA···Cg1ⁱ, C6A—H6AA···Cg2ⁱⁱ, C4B—H4B···Cg3ⁱⁱⁱ, and C6A—H6AA···Cg3^iv: (i) 1/2 - X, 1/2 + Y, 1/2 - Z; (ii) -1/2 + X, 1/2 - Y, 1/2 + Z; (iii) 1/2 + X, 3/2 - Y, 1/2 + Z; (iv) 1/2 - X, -3/2 + Y, 1/2 - Z; Cg1, Cg2 and Cg3 are the centroids of the C3A–C8A, N1B/C8B/C3B/C2B/C1B/C9B and N1C/C8C/C3C/C2C/C1C/C9C aromatic rings).

Related literature top

For the biological activities, molecular recognition and catalysis see, for example: Fournet et al. (2003); Yamada et al., (1981); Goswami & Mahapatra (1998); Goswami et al. (1989). Cg1, Cg2 and Cg3 are the centroids of the C3A–C8A, N1B/C8B/C3B/C2B/C1B/C9B and N1C/C8C/C3C/C2C/C1C/C9C rings, respectively.

Experimental top

2,2-dichloromethyl quinoline (1 mmol) was dissolved in dry benzene (25 mL). The anhydrous green colored Co^I(PPh₃)₃Cl (2.5 mmol) catalyst was added to the reaction mixture with stirring at room temperature under a nitrogen atmosphere. After 30 minutes, the color of the reaction mixture had changed from green to blue. The reaction mixture was then heated under reflux conditions for 2-3 h. The solvent was evaporated to dryness, the residue was worked up with water and the organic part was extracted with chloroform. The organic layer was dried (Na₂SO₄) and concentrated. Column chromatography of the crude product on silica gel and elution with methanol in chloroform afforded 1,2-di-(2-quinolyl)-ethylene. Single crystals suitable for X-ray diffraction were grown by slow evaporation of a CHCl₃-methanol (1:1) solution of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure showing 40% probability displacement ellipsoids and the atomic numbering. Open bonds indicate the minor component [symmetry code for C: -x + 1, -y + 2, -z and symmetry code for unlabelled atoms -x, -y, -z].
	Fig. 2. Crystal packing of viewed down the b-axis showing linking of molecules by intermolecular C—H···π interactions. Inermolecular interactions are drawn as dashed lines. Only the major component of the disordered molecule is shown.

1,2-Di-2-quinolylethene top

Crystal data top

C₂₀H₁₄N₂	F(000) = 592
M_r = 282.33	D_x = 1.296 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3767 reflections
a = 15.6378 (2) Å	θ = 2.7–31.5°
b = 6.0798 (1) Å	µ = 0.08 mm⁻¹
c = 16.0860 (2) Å	T = 100 K
β = 108.879 (1)°	Block, yellow
V = 1447.10 (4) Å³	0.34 × 0.33 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3317 independent reflections
Radiation source: fine-focus sealed tube	2476 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→20
T_min = 0.863, T_max = 0.993	k = −7→6
12910 measured reflections	l = −20→18

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0416P)² + 0.3849P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3317 reflections	Δρ_max = 0.25 e Å⁻³
245 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (10)

Crystal data top

C₂₀H₁₄N₂	V = 1447.10 (4) Å³
M_r = 282.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.6378 (2) Å	µ = 0.08 mm⁻¹
b = 6.0798 (1) Å	T = 100 K
c = 16.0860 (2) Å	0.34 × 0.33 × 0.09 mm
β = 108.879 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3317 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2476 reflections with I > 2σ(I)
T_min = 0.863, T_max = 0.993	R_int = 0.030
12910 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
3317 reflections	Δρ_min = −0.17 e Å⁻³
245 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.07166 (7)	0.04930 (18)	0.16586 (7)	0.0216 (3)
C1A	0.10529 (8)	0.3931 (2)	0.10857 (9)	0.0246 (3)
H1AA	0.1003	0.4797	0.0596	0.030*
C2A	0.14983 (8)	0.4706 (2)	0.19043 (9)	0.0247 (3)
H2AA	0.1749	0.6108	0.1977	0.030*
C3A	0.15781 (8)	0.3371 (2)	0.26439 (8)	0.0215 (3)
C4A	0.20530 (8)	0.4010 (2)	0.35202 (9)	0.0263 (3)
H4AA	0.2318	0.5395	0.3631	0.032*
C5A	0.21245 (8)	0.2605 (2)	0.42038 (9)	0.0281 (3)
H5AA	0.2442	0.3033	0.4776	0.034*
C6A	0.17178 (9)	0.0509 (2)	0.40428 (9)	0.0281 (3)
H6AA	0.1770	−0.0437	0.4511	0.034*
C7A	0.12485 (8)	−0.0149 (2)	0.32079 (9)	0.0248 (3)
H7AA	0.0977	−0.1528	0.3114	0.030*
C8A	0.11711 (8)	0.1247 (2)	0.24836 (8)	0.0201 (3)
C9A	0.06639 (8)	0.1799 (2)	0.09801 (8)	0.0218 (3)
C10A	0.01868 (8)	0.0993 (2)	0.00925 (8)	0.0232 (3)
H10A	0.0142	0.1934	−0.0375	0.028*
N1B	0.69538 (18)	0.8831 (3)	0.07847 (10)	0.0206 (5)	0.780 (6)
C1B	0.57855 (14)	0.6355 (5)	0.08990 (15)	0.0210 (5)	0.780 (6)
H1B	0.5174	0.6104	0.0801	0.025*	0.780 (6)
C2B	0.6415 (3)	0.4802 (7)	0.1311 (3)	0.0247 (9)	0.780 (6)
H2B	0.6231	0.3476	0.1486	0.030*	0.780 (6)
C3B	0.7367 (3)	0.5221 (6)	0.1476 (2)	0.0161 (7)	0.780 (6)
C4B	0.8065 (3)	0.3683 (7)	0.1894 (3)	0.0215 (9)	0.780 (6)
H4B	0.7918	0.2321	0.2072	0.026*	0.780 (6)
C5B	0.89117 (17)	0.4192 (6)	0.20252 (17)	0.0241 (6)	0.780 (6)
H5B	0.9360	0.3167	0.2284	0.029*	0.780 (6)
C6B	0.91586 (16)	0.6283 (5)	0.17789 (16)	0.0236 (6)	0.780 (6)
H6B	0.9765	0.6623	0.1891	0.028*	0.780 (6)
C7B	0.8505 (2)	0.7811 (4)	0.13753 (16)	0.0219 (5)	0.780 (6)
H7B	0.8670	0.9174	0.1213	0.026*	0.780 (6)
C8B	0.7575 (3)	0.7292 (7)	0.1208 (2)	0.0182 (7)	0.780 (6)
C9B	0.6082 (2)	0.8361 (4)	0.06227 (11)	0.0192 (5)	0.780 (6)
C10B	0.54504 (13)	1.0039 (3)	0.01229 (11)	0.0208 (6)	0.780 (6)
H10B	0.5703	1.1285	−0.0039	0.025*	0.780 (6)
N1C	0.3376 (6)	1.1411 (12)	−0.0755 (4)	0.0140 (16)*	0.220 (6)
C1C	0.4292 (7)	1.4289 (18)	−0.1047 (6)	0.026 (2)*	0.220 (6)
H1C	0.4870	1.4748	−0.1013	0.031*	0.220 (6)
C2C	0.3606 (11)	1.556 (3)	−0.1416 (11)	0.014 (3)*	0.220 (6)
H2C	0.3687	1.6944	−0.1628	0.017*	0.220 (6)
C3C	0.2813 (9)	1.486 (2)	−0.1479 (10)	0.011 (3)*	0.220 (6)
C4C	0.2057 (13)	1.604 (3)	−0.1817 (12)	0.024 (4)*	0.220 (6)
H4C	0.2120	1.7485	−0.1976	0.029*	0.220 (6)
C5C	0.1046 (7)	1.515 (2)	−0.1969 (7)	0.020 (3)*	0.220 (6)
H5C	0.0529	1.5947	−0.2263	0.025*	0.220 (6)
C6C	0.1025 (8)	1.3099 (17)	−0.1622 (6)	0.022 (2)*	0.220 (6)
H6C	0.0474	1.2482	−0.1645	0.026*	0.220 (6)
C7C	0.1792 (8)	1.197 (2)	−0.1248 (6)	0.026 (3)*	0.220 (6)
H7C	0.1743	1.0569	−0.1035	0.031*	0.220 (6)
C8C	0.2620 (12)	1.271 (4)	−0.1160 (13)	0.030 (5)*	0.220 (6)
C9C	0.4178 (6)	1.2225 (17)	−0.0697 (5)	0.0172 (18)*	0.220 (6)
C10C	0.4987 (5)	1.0882 (12)	−0.0238 (4)	0.023 (2)*	0.220 (6)
H10C	0.5533	1.1342	−0.0294	0.028*	0.220 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0207 (5)	0.0220 (6)	0.0214 (6)	0.0007 (4)	0.0058 (4)	−0.0004 (5)
C1A	0.0220 (6)	0.0249 (7)	0.0272 (7)	0.0016 (5)	0.0083 (5)	0.0051 (6)
C2A	0.0214 (6)	0.0195 (7)	0.0330 (8)	−0.0017 (5)	0.0084 (6)	−0.0009 (6)
C3A	0.0174 (6)	0.0220 (7)	0.0253 (7)	0.0022 (5)	0.0072 (5)	−0.0030 (5)
C4A	0.0227 (6)	0.0248 (7)	0.0301 (8)	0.0003 (5)	0.0068 (5)	−0.0085 (6)
C5A	0.0248 (7)	0.0365 (8)	0.0213 (7)	0.0032 (6)	0.0052 (5)	−0.0089 (6)
C6A	0.0282 (7)	0.0344 (8)	0.0222 (7)	0.0036 (6)	0.0088 (5)	0.0023 (6)
C7A	0.0250 (7)	0.0245 (7)	0.0251 (7)	−0.0009 (5)	0.0083 (5)	0.0005 (6)
C8A	0.0163 (6)	0.0215 (7)	0.0226 (7)	0.0012 (5)	0.0064 (5)	−0.0013 (5)
C9A	0.0189 (6)	0.0225 (7)	0.0236 (7)	0.0022 (5)	0.0065 (5)	0.0017 (5)
C10A	0.0214 (6)	0.0265 (7)	0.0209 (7)	0.0029 (5)	0.0058 (5)	0.0034 (6)
N1B	0.0168 (11)	0.0220 (9)	0.0217 (8)	−0.0001 (7)	0.0045 (7)	0.0001 (6)
C1B	0.0193 (9)	0.0226 (15)	0.0203 (10)	−0.0011 (9)	0.0051 (7)	−0.0014 (10)
C2B	0.0308 (15)	0.0216 (19)	0.0228 (16)	−0.0083 (12)	0.0103 (11)	−0.0013 (13)
C3B	0.0110 (15)	0.0222 (13)	0.0160 (11)	−0.0003 (12)	0.0056 (11)	−0.0020 (7)
C4B	0.0253 (17)	0.0185 (15)	0.0189 (14)	0.0117 (12)	0.0048 (11)	0.0069 (10)
C5B	0.0255 (12)	0.0219 (15)	0.0244 (11)	0.0049 (11)	0.0074 (8)	0.0034 (11)
C6B	0.0194 (11)	0.0273 (14)	0.0233 (11)	0.0025 (11)	0.0057 (8)	0.0023 (10)
C7B	0.0179 (13)	0.0234 (11)	0.0258 (11)	−0.0020 (11)	0.0089 (10)	−0.0010 (9)
C8B	0.022 (2)	0.0188 (13)	0.0133 (12)	0.0004 (14)	0.0051 (12)	−0.0022 (7)
C9B	0.0188 (11)	0.0192 (11)	0.0195 (9)	−0.0017 (9)	0.0061 (8)	−0.0012 (7)
C10B	0.0214 (11)	0.0190 (10)	0.0214 (9)	−0.0012 (7)	0.0061 (7)	0.0009 (7)

Geometric parameters (Å, º) top

N1A—C9A	1.3307 (16)	C4B—H4B	0.9300
N1A—C8A	1.3661 (15)	C5B—C6B	1.422 (4)
C1A—C2A	1.3592 (18)	C5B—H5B	0.9300
C1A—C9A	1.4183 (18)	C6B—C7B	1.378 (3)
C1A—H1AA	0.9300	C6B—H6B	0.9300
C2A—C3A	1.4118 (18)	C7B—C8B	1.426 (5)
C2A—H2AA	0.9300	C7B—H7B	0.9300
C3A—C4A	1.4183 (17)	C9B—C10B	1.466 (3)
C3A—C8A	1.4259 (18)	C10B—C10Bⁱⁱ	1.335 (4)
C4A—C5A	1.3683 (19)	C10B—H10B	0.9300
C4A—H4AA	0.9300	N1C—C9C	1.324 (9)
C5A—C6A	1.411 (2)	N1C—C8C	1.40 (2)
C5A—H5AA	0.9300	C1C—C2C	1.30 (2)
C6A—C7A	1.3652 (18)	C1C—C9C	1.410 (10)
C6A—H6AA	0.9300	C1C—H1C	0.9300
C7A—C8A	1.4146 (18)	C2C—C3C	1.28 (2)
C7A—H7AA	0.9300	C2C—H2C	0.9300
C9A—C10A	1.4650 (17)	C3C—C4C	1.34 (2)
C10A—C10Aⁱ	1.332 (3)	C3C—C8C	1.47 (3)
C10A—H10A	0.9300	C4C—C5C	1.61 (2)
N1B—C9B	1.333 (3)	C4C—H4C	0.9300
N1B—C8B	1.362 (5)	C5C—C6C	1.371 (13)
C1B—C2B	1.370 (5)	C5C—H5C	0.9300
C1B—C9B	1.426 (3)	C6C—C7C	1.344 (11)
C1B—H1B	0.9300	C6C—H6C	0.9300
C2B—C3B	1.448 (6)	C7C—C8C	1.335 (18)
C2B—H2B	0.9300	C7C—H7C	0.9300
C3B—C8B	1.403 (6)	C9C—C10C	1.486 (11)
C3B—C4B	1.429 (5)	C10C—C10Cⁱⁱ	1.311 (15)
C4B—C5B	1.308 (6)	C10C—H10C	0.9300

C9A—N1A—C8A	118.11 (11)	C7B—C6B—C5B	120.5 (2)
C2A—C1A—C9A	119.88 (12)	C7B—C6B—H6B	119.8
C2A—C1A—H1AA	120.1	C5B—C6B—H6B	119.8
C9A—C1A—H1AA	120.1	C6B—C7B—C8B	119.7 (2)
C1A—C2A—C3A	119.68 (12)	C6B—C7B—H7B	120.2
C1A—C2A—H2AA	120.2	C8B—C7B—H7B	120.2
C3A—C2A—H2AA	120.2	N1B—C8B—C3B	124.8 (4)
C2A—C3A—C4A	123.73 (12)	N1B—C8B—C7B	117.5 (3)
C2A—C3A—C8A	117.09 (11)	C3B—C8B—C7B	117.7 (3)
C4A—C3A—C8A	119.16 (12)	N1B—C9B—C1B	122.53 (17)
C5A—C4A—C3A	120.54 (13)	N1B—C9B—C10B	115.0 (2)
C5A—C4A—H4AA	119.7	C1B—C9B—C10B	122.4 (2)
C3A—C4A—H4AA	119.7	C10Bⁱⁱ—C10B—C9B	126.7 (2)
C4A—C5A—C6A	120.12 (12)	C10Bⁱⁱ—C10B—H10B	116.7
C4A—C5A—H5AA	119.9	C9B—C10B—H10B	116.7
C6A—C5A—H5AA	119.9	C9C—N1C—C8C	117.5 (11)
C7A—C6A—C5A	120.80 (13)	C2C—C1C—C9C	121.4 (10)
C7A—C6A—H6AA	119.6	C2C—C1C—H1C	119.3
C5A—C6A—H6AA	119.6	C9C—C1C—H1C	119.3
C6A—C7A—C8A	120.67 (13)	C3C—C2C—C1C	118.0 (14)
C6A—C7A—H7AA	119.7	C3C—C2C—H2C	121.0
C8A—C7A—H7AA	119.7	C1C—C2C—H2C	121.0
N1A—C8A—C7A	118.54 (12)	C2C—C3C—C4C	123.7 (16)
N1A—C8A—C3A	122.77 (12)	C2C—C3C—C8C	124.9 (14)
C7A—C8A—C3A	118.69 (11)	C4C—C3C—C8C	111.4 (14)
N1A—C9A—C1A	122.47 (12)	C3C—C4C—C5C	125.1 (14)
N1A—C9A—C10A	118.44 (12)	C3C—C4C—H4C	117.5
C1A—C9A—C10A	119.09 (12)	C5C—C4C—H4C	117.5
C10Aⁱ—C10A—C9A	124.71 (15)	C6C—C5C—C4C	113.2 (10)
C10Aⁱ—C10A—H10A	117.6	C6C—C5C—H5C	123.4
C9A—C10A—H10A	117.6	C4C—C5C—H5C	123.4
C9B—N1B—C8B	118.0 (3)	C7C—C6C—C5C	120.8 (11)
C2B—C1B—C9B	119.0 (2)	C7C—C6C—H6C	119.6
C2B—C1B—H1B	120.5	C5C—C6C—H6C	119.6
C9B—C1B—H1B	120.5	C8C—C7C—C6C	124.7 (14)
C1B—C2B—C3B	120.2 (3)	C8C—C7C—H7C	117.7
C1B—C2B—H2B	119.9	C6C—C7C—H7C	117.7
C3B—C2B—H2B	119.9	C7C—C8C—N1C	120.2 (18)
C8B—C3B—C4B	120.9 (4)	C7C—C8C—C3C	124.4 (16)
C8B—C3B—C2B	115.4 (4)	N1C—C8C—C3C	115.3 (14)
C4B—C3B—C2B	123.7 (4)	N1C—C9C—C1C	122.9 (8)
C5B—C4B—C3B	120.0 (4)	N1C—C9C—C10C	117.7 (9)
C5B—C4B—H4B	120.0	C1C—C9C—C10C	119.3 (9)
C3B—C4B—H4B	120.0	C10Cⁱⁱ—C10C—C9C	126.9 (9)
C4B—C5B—C6B	121.2 (3)	C10Cⁱⁱ—C10C—H10C	116.6
C4B—C5B—H5B	119.4	C9C—C10C—H10C	116.6
C6B—C5B—H5B	119.4

C9A—C1A—C2A—C3A	0.64 (18)	C2B—C3B—C8B—N1B	−2.9 (5)
C1A—C2A—C3A—C4A	178.00 (12)	C4B—C3B—C8B—C7B	−0.6 (5)
C1A—C2A—C3A—C8A	−0.46 (17)	C2B—C3B—C8B—C7B	178.5 (3)
C2A—C3A—C4A—C5A	−178.12 (12)	C6B—C7B—C8B—N1B	−178.1 (2)
C8A—C3A—C4A—C5A	0.32 (18)	C6B—C7B—C8B—C3B	0.6 (4)
C3A—C4A—C5A—C6A	−0.58 (19)	C8B—N1B—C9B—C1B	2.0 (3)
C4A—C5A—C6A—C7A	−0.06 (19)	C8B—N1B—C9B—C10B	−176.8 (2)
C5A—C6A—C7A—C8A	0.96 (19)	C2B—C1B—C9B—N1B	−3.1 (3)
C9A—N1A—C8A—C7A	−178.59 (11)	C2B—C1B—C9B—C10B	175.6 (3)
C9A—N1A—C8A—C3A	0.75 (17)	N1B—C9B—C10B—C10Bⁱⁱ	179.9 (2)
C6A—C7A—C8A—N1A	178.17 (11)	C1B—C9B—C10B—C10Bⁱⁱ	1.1 (3)
C6A—C7A—C8A—C3A	−1.20 (18)	C9C—C1C—C2C—C3C	−2 (2)
C2A—C3A—C8A—N1A	−0.24 (17)	C1C—C2C—C3C—C4C	177.6 (16)
C4A—C3A—C8A—N1A	−178.78 (11)	C1C—C2C—C3C—C8C	0 (3)
C2A—C3A—C8A—C7A	179.10 (11)	C2C—C3C—C4C—C5C	175.5 (15)
C4A—C3A—C8A—C7A	0.56 (17)	C8C—C3C—C4C—C5C	−7 (2)
C8A—N1A—C9A—C1A	−0.58 (17)	C3C—C4C—C5C—C6C	7 (2)
C8A—N1A—C9A—C10A	179.29 (10)	C4C—C5C—C6C—C7C	−3.8 (16)
C2A—C1A—C9A—N1A	−0.11 (19)	C5C—C6C—C7C—C8C	2 (2)
C2A—C1A—C9A—C10A	−179.98 (11)	C6C—C7C—C8C—N1C	179.5 (11)
N1A—C9A—C10A—C10Aⁱ	−1.6 (2)	C6C—C7C—C8C—C3C	−1 (3)
C1A—C9A—C10A—C10Aⁱ	178.32 (15)	C9C—N1C—C8C—C7C	179.2 (13)
C9B—C1B—C2B—C3B	1.1 (5)	C9C—N1C—C8C—C3C	0.2 (19)
C1B—C2B—C3B—C8B	1.6 (6)	C2C—C3C—C8C—C7C	−178.3 (17)
C1B—C2B—C3B—C4B	−179.3 (4)	C4C—C3C—C8C—C7C	4 (3)
C8B—C3B—C4B—C5B	−0.5 (6)	C2C—C3C—C8C—N1C	1 (2)
C2B—C3B—C4B—C5B	−179.5 (4)	C4C—C3C—C8C—N1C	−176.8 (15)
C3B—C4B—C5B—C6B	1.6 (6)	C8C—N1C—C9C—C1C	−2.0 (15)
C4B—C5B—C6B—C7B	−1.5 (4)	C8C—N1C—C9C—C10C	177.9 (10)
C5B—C6B—C7B—C8B	0.3 (4)	C2C—C1C—C9C—N1C	3.2 (16)
C9B—N1B—C8B—C3B	1.1 (4)	C2C—C1C—C9C—C10C	−176.7 (11)
C9B—N1B—C8B—C7B	179.8 (2)	N1C—C9C—C10C—C10Cⁱⁱ	−11.3 (12)
C4B—C3B—C8B—N1B	178.1 (3)	C1C—C9C—C10C—C10Cⁱⁱ	168.6 (9)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2AA···Cg1ⁱⁱⁱ	0.93	2.77	3.3409 (14)	121
C6A—H6AA···Cg2^iv	0.93	2.65	3.5328 (18)	159
C4B—H4B···Cg3^v	0.93	2.85	3.376 (12)	116
C6A—H6AA···Cg3^vi	0.93	2.76	3.613 (10)	152

Symmetry codes: (iii) −x+1/2, y+1/2, −z+1/2; (iv) x−3/2, −y−1/2, z−1/2; (v) x−1/2, −y+1/2, z−1/2; (vi) −x+1/2, y−3/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄N₂
M_r	282.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	15.6378 (2), 6.0798 (1), 16.0860 (2)
β (°)	108.879 (1)
V (Å³)	1447.10 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.34 × 0.33 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.863, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	12910, 3317, 2476
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.04
No. of reflections	3317
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.17

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2AA···Cg1ⁱ	0.9300	2.77	3.3409 (14)	121
C6A—H6AA···Cg2ⁱⁱ	0.9300	2.65	3.5328 (18)	159
C4B—H4B···Cg3ⁱⁱⁱ	0.9300	2.85	3.376 (12)	116
C6A—H6AA···Cg3^iv	0.9300	2.76	3.613 (10)	152

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−3/2, −y−1/2, z−1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1/2, y−3/2, −z+1/2.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. We thank the DST [SR/S1/OC-13/2005], Goverment of India, for financial support. ACM thanks the UGC, Goverment of India, for a fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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