1-Diphenyl­methyl­ene-2-(9H-fluoren-9-yl­idene)hydrazine

Archana, R.; Anbazhagan, R.; Sankaran, K.R.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S160053681000070X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o345

https://doi.org/10.1107/S160053681000070X

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1-Diphenylmethylene-2-(9H-fluoren-9-ylidene)hydrazine

R. Archana,^a R. Anbazhagan,^b K. R. Sankaran,^b A. Thiruvalluvar ^a ^* 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 4 January 2010; accepted 6 January 2010; online 13 January 2010)

In the title molecule, C₂₆H₁₈N₂, the 9H-fluorene unit is almost planar, as the cyclopentadiene ring makes dihedral angles of 1.12 (6) and 1.46 (6)° with the fused benzene rings. The dihedral angle between the two phenyl rings of the diphenylmethylene residue is 61.78 (6)°.

Related literature

For the synthesis, see: Lewis & Glaser (2002 ). For the crystal structures of some aromatic azines, for example, fluorenone azine, see: Hagen et al. (1977 ). For the other heterocyclic aldehyde azines, see: Chen et al. (1995 ). For quadratic nonlinear optical properties, see: Wolff & Wortmann (1999 ).

Experimental

Crystal data

C₂₆H₁₈N₂
M_r = 358.42
Monoclinic, C 2/c
a = 22.8362 (3) Å
b = 13.1432 (2) Å
c = 12.4642 (2) Å
β = 92.874 (1)°
V = 3736.31 (10) Å³
Z = 8
Cu Kα radiation
μ = 0.58 mm⁻¹
T = 110 K
0.46 × 0.41 × 0.32 mm

Data collection

Oxford Xcalibur diffractometer with a Ruby Gemini detector
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.955, T_max = 1.000
7177 measured reflections
3682 independent reflections
3147 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.102
S = 1.06
3682 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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: https://doi.org/10.1107/S160053681000070X/tk2612sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681000070X/tk2612Isup2.hkl

checkCIF report

Comment top

Azines have received attention due to their unusual reactivity and spectral properties. For instance they are potential nonlinear optical (NLO) material. Molecular materials with quadratic nonlinear optical properties are currently attracting considerable interest (Wolff & Wortmann, 1999; Chen et al., 1995). Some crystal structures are known (Hagen et al., 1977). Optoelectronics has stimulated the search of highly nonlinear organic crystals for efficient signal processing. The title compound is an example of unsymmetrical fluorenone azine and shows a nonlinear optical behaviour. Herein, we report its crystal structure.

In the title molecule, C₂₆H₁₈N₂, the 9H-fluorene unit is planar. The cyclopentadiene ring makes dihedral angles of 1.12 (6)° and 1.46 (6)° with the fused benzene rings. The dihedral angle between the two phenyl rings of the diphenylmethylene residue is 61.78 (6)°.

Related literature top

For the synthesis, see: Lewis & Glaser (2002). For the crystal structures of some aromatic azines, for example, fluorenone azine, see: Hagen et al. (1977). For the other heterocyclic aldehyde azines, see: Chen et al. (1995). For quadratic nonlinear optical properties, see: Wolff & Wortmann (1999).

Experimental top

The compound was prepared in accord with literature precedents Lewis & Glaser (2002). The mixture of fluorenone hydrazone (1.94 g, 0.01 mol) and benzophenone (1.82 g, 0.01 mol) in ethanol with acetic acid was refluxed for 2 h. A mixture was cooled to room temperature over several hours. The solid obtained was separated, dried and then recrystallized from absolute ethanol. The yield of isolated product was (3.07 g, 78%).

Structure description top

For the synthesis, see: Lewis & Glaser (2002). For the crystal structures of some aromatic azines, for example, fluorenone azine, see: Hagen et al. (1977). For the other heterocyclic aldehyde azines, see: Chen et al. (1995). For quadratic nonlinear optical properties, see: Wolff & Wortmann (1999).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

1-Diphenylmethylene-2-(9H-fluoren-9-ylidene)hydrazine top

Crystal data top

C₂₆H₁₈N₂	F(000) = 1504
M_r = 358.42	D_x = 1.274 Mg m⁻³
Monoclinic, C2/c	Melting point: 377 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54184 Å
a = 22.8362 (3) Å	Cell parameters from 4987 reflections
b = 13.1432 (2) Å	θ = 5.1–73.9°
c = 12.4642 (2) Å	µ = 0.58 mm⁻¹
β = 92.874 (1)°	T = 110 K
V = 3736.31 (10) Å³	Chunk, pale-yellow
Z = 8	0.46 × 0.41 × 0.32 mm

Data collection top

Oxford Xcalibur diffractometer with a Ruby Gemini detector	3682 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3147 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.1°, θ_min = 5.2°
ω scans	h = −27→28
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→15
T_min = 0.955, T_max = 1.000	l = −14→15
7177 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0563P)² + 1.6279P] where P = (F_o² + 2F_c²)/3
3682 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₆H₁₈N₂	V = 3736.31 (10) Å³
M_r = 358.42	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 22.8362 (3) Å	µ = 0.58 mm⁻¹
b = 13.1432 (2) Å	T = 110 K
c = 12.4642 (2) Å	0.46 × 0.41 × 0.32 mm
β = 92.874 (1)°

Data collection top

Oxford Xcalibur diffractometer with a Ruby Gemini detector	3682 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3147 reflections with I > 2σ(I)
T_min = 0.955, T_max = 1.000	R_int = 0.019
7177 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
3682 reflections	Δρ_min = −0.20 e Å⁻³
253 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	0.35481 (4)	0.16268 (8)	0.34487 (8)	0.0276 (3)
N2	0.30117 (4)	0.20980 (8)	0.32203 (8)	0.0266 (3)
C1	0.48097 (6)	0.08981 (10)	0.38410 (10)	0.0325 (4)
C2	0.54135 (6)	0.07751 (12)	0.40371 (11)	0.0381 (4)
C3	0.57819 (6)	0.16072 (12)	0.41540 (11)	0.0385 (4)
C4	0.55662 (6)	0.25969 (11)	0.40685 (10)	0.0329 (4)
C4A	0.49686 (5)	0.27237 (10)	0.38678 (9)	0.0264 (3)
C4B	0.46148 (5)	0.36564 (10)	0.37429 (9)	0.0252 (3)
C5	0.47889 (5)	0.46657 (10)	0.37629 (9)	0.0291 (4)
C6	0.43594 (6)	0.54174 (10)	0.36409 (10)	0.0309 (4)
C7	0.37714 (6)	0.51540 (10)	0.35090 (9)	0.0295 (4)
C8	0.35919 (5)	0.41379 (10)	0.34822 (9)	0.0262 (3)
C8A	0.40189 (5)	0.33819 (9)	0.35879 (9)	0.0238 (3)
C9	0.39839 (5)	0.22522 (9)	0.35779 (9)	0.0247 (3)
C9A	0.45920 (5)	0.18833 (10)	0.37629 (9)	0.0266 (3)
C10	0.25572 (5)	0.16399 (9)	0.35694 (9)	0.0225 (3)
C11	0.25793 (5)	0.07200 (8)	0.42731 (9)	0.0215 (3)
C12	0.22316 (5)	−0.01253 (9)	0.39994 (9)	0.0259 (3)
C13	0.22468 (5)	−0.09829 (9)	0.46475 (10)	0.0281 (3)
C14	0.25979 (5)	−0.09989 (9)	0.55906 (10)	0.0277 (3)
C15	0.29376 (5)	−0.01569 (9)	0.58763 (9)	0.0264 (3)
C16	0.29369 (5)	0.06937 (9)	0.52151 (9)	0.0233 (3)
C21	0.19789 (5)	0.20994 (9)	0.32457 (9)	0.0226 (3)
C22	0.19408 (5)	0.28377 (9)	0.24323 (9)	0.0257 (3)
C23	0.14141 (6)	0.33068 (10)	0.21489 (10)	0.0319 (4)
C24	0.09125 (6)	0.30600 (11)	0.26812 (11)	0.0348 (4)
C25	0.09424 (5)	0.23372 (10)	0.34938 (10)	0.0307 (4)
C26	0.14706 (5)	0.18576 (9)	0.37725 (9)	0.0251 (3)
H1	0.45565	0.03265	0.37637	0.0390*
H2	0.55735	0.01088	0.40909	0.0457*
H3	0.61900	0.15017	0.42955	0.0462*
H4	0.58209	0.31666	0.41454	0.0395*
H5	0.51916	0.48422	0.38577	0.0350*
H6	0.44700	0.61143	0.36480	0.0370*
H7	0.34848	0.56765	0.34354	0.0355*
H8	0.31883	0.39663	0.33940	0.0315*
H12	0.19833	−0.01119	0.33649	0.0310*
H13	0.20167	−0.15608	0.44465	0.0337*
H14	0.26053	−0.15842	0.60383	0.0332*
H15	0.31719	−0.01624	0.65280	0.0317*
H16	0.31802	0.12588	0.54040	0.0279*
H22	0.22823	0.30178	0.20708	0.0308*
H23	0.13947	0.37987	0.15898	0.0382*
H24	0.05507	0.33849	0.24892	0.0417*
H25	0.06007	0.21698	0.38608	0.0369*
H26	0.14866	0.13604	0.43264	0.0301*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0245 (5)	0.0310 (5)	0.0277 (5)	0.0046 (4)	0.0057 (4)	0.0066 (4)
N2	0.0237 (5)	0.0284 (5)	0.0279 (5)	0.0023 (4)	0.0034 (4)	0.0040 (4)
C1	0.0348 (7)	0.0340 (7)	0.0293 (6)	0.0097 (5)	0.0066 (5)	0.0068 (5)
C2	0.0384 (7)	0.0428 (8)	0.0334 (7)	0.0195 (6)	0.0056 (6)	0.0080 (6)
C3	0.0270 (6)	0.0556 (9)	0.0328 (7)	0.0157 (6)	0.0012 (5)	0.0020 (6)
C4	0.0252 (6)	0.0463 (8)	0.0273 (6)	0.0066 (5)	0.0011 (5)	−0.0002 (5)
C4A	0.0263 (6)	0.0356 (7)	0.0174 (5)	0.0066 (5)	0.0036 (4)	0.0022 (5)
C4B	0.0245 (5)	0.0346 (7)	0.0167 (5)	0.0055 (5)	0.0023 (4)	0.0011 (4)
C5	0.0276 (6)	0.0364 (7)	0.0233 (6)	0.0004 (5)	0.0003 (5)	−0.0011 (5)
C6	0.0379 (7)	0.0302 (6)	0.0245 (6)	0.0014 (5)	0.0011 (5)	−0.0001 (5)
C7	0.0343 (7)	0.0320 (7)	0.0224 (6)	0.0103 (5)	0.0023 (5)	0.0028 (5)
C8	0.0242 (5)	0.0336 (6)	0.0210 (5)	0.0069 (5)	0.0028 (4)	0.0044 (5)
C8A	0.0247 (6)	0.0314 (6)	0.0157 (5)	0.0036 (5)	0.0039 (4)	0.0034 (4)
C9	0.0240 (6)	0.0310 (6)	0.0195 (5)	0.0056 (4)	0.0060 (4)	0.0059 (4)
C9A	0.0254 (6)	0.0350 (7)	0.0198 (5)	0.0067 (5)	0.0055 (4)	0.0050 (5)
C10	0.0261 (6)	0.0219 (6)	0.0198 (5)	0.0001 (4)	0.0029 (4)	−0.0030 (4)
C11	0.0229 (5)	0.0207 (5)	0.0214 (5)	0.0021 (4)	0.0051 (4)	−0.0015 (4)
C12	0.0282 (6)	0.0255 (6)	0.0240 (5)	−0.0002 (5)	0.0022 (4)	−0.0043 (5)
C13	0.0291 (6)	0.0205 (6)	0.0354 (6)	−0.0017 (4)	0.0086 (5)	−0.0045 (5)
C14	0.0299 (6)	0.0221 (6)	0.0318 (6)	0.0065 (5)	0.0100 (5)	0.0046 (5)
C15	0.0270 (6)	0.0279 (6)	0.0245 (6)	0.0077 (5)	0.0026 (4)	0.0009 (5)
C16	0.0232 (5)	0.0220 (5)	0.0248 (6)	0.0016 (4)	0.0036 (4)	−0.0036 (4)
C21	0.0262 (6)	0.0213 (5)	0.0202 (5)	0.0000 (4)	0.0015 (4)	−0.0038 (4)
C22	0.0289 (6)	0.0251 (6)	0.0233 (6)	0.0005 (5)	0.0035 (4)	−0.0010 (4)
C23	0.0347 (7)	0.0315 (7)	0.0291 (6)	0.0053 (5)	−0.0012 (5)	0.0031 (5)
C24	0.0274 (6)	0.0375 (7)	0.0389 (7)	0.0072 (5)	−0.0029 (5)	−0.0018 (6)
C25	0.0241 (6)	0.0344 (7)	0.0339 (7)	−0.0012 (5)	0.0043 (5)	−0.0048 (5)
C26	0.0276 (6)	0.0245 (6)	0.0232 (5)	−0.0018 (4)	0.0029 (4)	−0.0029 (4)

Geometric parameters (Å, º) top

N1—N2	1.3893 (13)	C15—C16	1.3889 (16)
N1—C9	1.2946 (15)	C21—C22	1.4029 (16)
N2—C10	1.2940 (15)	C21—C26	1.3986 (16)
C1—C2	1.3976 (19)	C22—C23	1.3817 (18)
C1—C9A	1.3887 (18)	C23—C24	1.3906 (19)
C2—C3	1.383 (2)	C24—C25	1.3878 (19)
C3—C4	1.393 (2)	C25—C26	1.3896 (17)
C4—C4A	1.3851 (18)	C1—H1	0.9500
C4A—C4B	1.4721 (18)	C2—H2	0.9500
C4A—C9A	1.4020 (18)	C3—H3	0.9500
C4B—C5	1.3847 (18)	C4—H4	0.9500
C4B—C8A	1.4117 (16)	C5—H5	0.9500
C5—C6	1.3951 (18)	C6—H6	0.9500
C6—C7	1.3884 (19)	C7—H7	0.9500
C7—C8	1.3969 (19)	C8—H8	0.9500
C8—C8A	1.3938 (17)	C12—H12	0.9500
C8A—C9	1.4870 (17)	C13—H13	0.9500
C9—C9A	1.4780 (16)	C14—H14	0.9500
C10—C11	1.4931 (16)	C15—H15	0.9500
C10—C21	1.4893 (16)	C16—H16	0.9500
C11—C12	1.3979 (16)	C22—H22	0.9500
C11—C16	1.3966 (16)	C23—H23	0.9500
C12—C13	1.3862 (17)	C24—H24	0.9500
C13—C14	1.3895 (17)	C25—H25	0.9500
C14—C15	1.3877 (17)	C26—H26	0.9500

N1···C16	2.9339 (15)	C21···H7^vii	2.9600
N2···C8	3.0012 (16)	C21···H16^v	2.7700
N1···H1	2.8800	C22···H14ⁱ	2.8800
N1···H16	2.6600	C22···H16^v	2.9700
N2···H8	2.5000	C23···H15^v	3.0700
N2···H16	2.9400	C25···H16^v	3.0100
N2···H22	2.4600	C26···H12	2.9000
N2···H14ⁱ	2.9100	C26···H16^v	2.7800
C1···C1ⁱⁱ	3.4960 (18)	H1···N1	2.8800
C1···C2ⁱⁱⁱ	3.4966 (19)	H1···C2ⁱⁱⁱ	3.1000
C2···C1ⁱⁱⁱ	3.4966 (19)	H2···C1ⁱⁱⁱ	3.0600
C3···C9ⁱⁱ	3.5752 (18)	H3···C14ⁱⁱⁱ	2.8400
C3···C15ⁱⁱⁱ	3.4924 (18)	H3···C15ⁱⁱⁱ	2.6800
C4···C9ⁱⁱ	3.5328 (17)	H3···H15ⁱⁱⁱ	2.5300
C4A···C4Aⁱⁱ	3.4199 (16)	H4···C5	3.0900
C5···C5ⁱⁱ	3.3384 (16)	H5···C4	3.0800
C5···C5^iv	3.3036 (16)	H5···C5^iv	3.0300
C7···C14^v	3.5528 (18)	H7···C21^vi	2.9600
C7···C13^v	3.5226 (17)	H7···C13^v	3.0100
C8···N2	3.0012 (16)	H7···C14^v	2.8400
C8A···C26^v	3.5415 (16)	H8···N2	2.5000
C9···C4ⁱⁱ	3.5328 (17)	H8···H12^vi	2.5200
C9···C3ⁱⁱ	3.5752 (18)	H12···C21	2.9100
C12···C26	3.1373 (17)	H12···C26	2.9000
C13···C7^v	3.5226 (17)	H12···H26	2.5700
C14···C7^v	3.5528 (18)	H12···C7^vii	2.8500
C15···C3ⁱⁱⁱ	3.4924 (18)	H12···C8^vii	2.7700
C16···N1	2.9339 (15)	H12···H8^vii	2.5200
C16···C22^v	3.5100 (16)	H13···H22^vii	2.6000
C16···C21^v	3.4776 (16)	H14···N2^viii	2.9100
C21···C16^v	3.4776 (16)	H14···C22^viii	2.8800
C22···C16^v	3.5100 (16)	H14···H22^viii	2.4200
C26···C8A^v	3.5415 (16)	H15···H3ⁱⁱⁱ	2.5300
C26···C12	3.1373 (17)	H15···C23^v	3.0700
C1···H2ⁱⁱⁱ	3.0600	H16···N1	2.6600
C2···H1ⁱⁱⁱ	3.1000	H16···N2	2.9400
C4···H5	3.0800	H16···C21^v	2.7700
C5···H4	3.0900	H16···C22^v	2.9700
C5···H5^iv	3.0300	H16···C25^v	3.0100
C7···H12^vi	2.8500	H16···C26^v	2.7800
C8···H26^v	2.8200	H22···N2	2.4600
C8···H12^vi	2.7700	H22···H14ⁱ	2.4200
C8A···H26^v	2.9200	H22···C12^vi	3.0200
C11···H26	2.6400	H22···C13^vi	2.7700
C12···H26	2.6300	H22···H13^vi	2.6000
C12···H22^vii	3.0200	H24···H24^ix	2.5200
C13···H22^vii	2.7700	H26···C11	2.6400
C13···H7^v	3.0100	H26···C12	2.6300
C14···H7^v	2.8400	H26···H12	2.5700
C14···H3ⁱⁱⁱ	2.8400	H26···C8^v	2.8200
C15···H3ⁱⁱⁱ	2.6800	H26···C8A^v	2.9200
C21···H12	2.9100

N2—N1—C9	114.01 (10)	C22—C23—C24	120.09 (12)
N1—N2—C10	115.95 (10)	C23—C24—C25	119.76 (12)
C2—C1—C9A	117.82 (12)	C24—C25—C26	120.22 (11)
C1—C2—C3	121.10 (14)	C21—C26—C25	120.67 (11)
C2—C3—C4	121.29 (13)	C2—C1—H1	121.00
C3—C4—C4A	117.88 (13)	C9A—C1—H1	121.00
C4—C4A—C4B	130.53 (12)	C1—C2—H2	119.00
C4—C4A—C9A	121.08 (12)	C3—C2—H2	119.00
C4B—C4A—C9A	108.38 (10)	C2—C3—H3	119.00
C4A—C4B—C5	129.81 (11)	C4—C3—H3	119.00
C4A—C4B—C8A	108.77 (11)	C3—C4—H4	121.00
C5—C4B—C8A	121.41 (11)	C4A—C4—H4	121.00
C4B—C5—C6	118.48 (11)	C4B—C5—H5	121.00
C5—C6—C7	120.45 (12)	C6—C5—H5	121.00
C6—C7—C8	121.47 (12)	C5—C6—H6	120.00
C7—C8—C8A	118.44 (11)	C7—C6—H6	120.00
C4B—C8A—C8	119.72 (11)	C6—C7—H7	119.00
C4B—C8A—C9	107.90 (10)	C8—C7—H7	119.00
C8—C8A—C9	132.38 (11)	C7—C8—H8	121.00
N1—C9—C8A	132.51 (11)	C8A—C8—H8	121.00
N1—C9—C9A	121.43 (11)	C11—C12—H12	120.00
C8A—C9—C9A	106.06 (10)	C13—C12—H12	120.00
C1—C9A—C4A	120.82 (11)	C12—C13—H13	120.00
C1—C9A—C9	130.32 (12)	C14—C13—H13	120.00
C4A—C9A—C9	108.86 (11)	C13—C14—H14	120.00
N2—C10—C11	124.77 (10)	C15—C14—H14	120.00
N2—C10—C21	115.82 (10)	C14—C15—H15	120.00
C11—C10—C21	119.40 (10)	C16—C15—H15	120.00
C10—C11—C12	119.88 (10)	C11—C16—H16	120.00
C10—C11—C16	121.00 (10)	C15—C16—H16	120.00
C12—C11—C16	119.11 (10)	C21—C22—H22	120.00
C11—C12—C13	120.45 (10)	C23—C22—H22	119.00
C12—C13—C14	120.12 (11)	C22—C23—H23	120.00
C13—C14—C15	119.77 (11)	C24—C23—H23	120.00
C14—C15—C16	120.38 (11)	C23—C24—H24	120.00
C11—C16—C15	120.13 (11)	C25—C24—H24	120.00
C10—C21—C22	119.89 (10)	C24—C25—H25	120.00
C10—C21—C26	121.75 (10)	C26—C25—H25	120.00
C22—C21—C26	118.27 (10)	C21—C26—H26	120.00
C21—C22—C23	121.00 (11)	C25—C26—H26	120.00

C9—N1—N2—C10	−148.47 (11)	C4B—C8A—C9—C9A	1.37 (12)
N2—N1—C9—C8A	3.86 (18)	C8—C8A—C9—N1	1.5 (2)
N2—N1—C9—C9A	−176.38 (10)	C8—C8A—C9—C9A	−178.31 (12)
N1—N2—C10—C11	6.19 (17)	N1—C9—C9A—C1	−0.58 (19)
N1—N2—C10—C21	−175.08 (10)	N1—C9—C9A—C4A	179.70 (11)
C9A—C1—C2—C3	0.26 (19)	C8A—C9—C9A—C1	179.24 (12)
C2—C1—C9A—C4A	0.60 (18)	C8A—C9—C9A—C4A	−0.49 (12)
C2—C1—C9A—C9	−179.09 (12)	N2—C10—C11—C12	−130.13 (13)
C1—C2—C3—C4	−0.8 (2)	N2—C10—C11—C16	50.85 (17)
C2—C3—C4—C4A	0.35 (19)	C21—C10—C11—C12	51.19 (15)
C3—C4—C4A—C4B	179.63 (12)	C21—C10—C11—C16	−127.84 (12)
C3—C4—C4A—C9A	0.52 (18)	N2—C10—C21—C22	13.12 (16)
C4—C4A—C4B—C5	2.1 (2)	N2—C10—C21—C26	−163.26 (11)
C4—C4A—C4B—C8A	−177.76 (12)	C11—C10—C21—C22	−168.08 (10)
C9A—C4A—C4B—C5	−178.73 (12)	C11—C10—C21—C26	15.54 (17)
C9A—C4A—C4B—C8A	1.44 (13)	C10—C11—C12—C13	−179.81 (11)
C4—C4A—C9A—C1	−1.01 (18)	C16—C11—C12—C13	−0.77 (17)
C4—C4A—C9A—C9	178.74 (11)	C10—C11—C16—C15	177.99 (11)
C4B—C4A—C9A—C1	179.70 (11)	C12—C11—C16—C15	−1.05 (17)
C4B—C4A—C9A—C9	−0.55 (13)	C11—C12—C13—C14	1.60 (18)
C4A—C4B—C5—C6	−178.91 (11)	C12—C13—C14—C15	−0.61 (18)
C8A—C4B—C5—C6	0.90 (17)	C13—C14—C15—C16	−1.21 (17)
C4A—C4B—C8A—C8	178.01 (10)	C14—C15—C16—C11	2.04 (17)
C4A—C4B—C8A—C9	−1.72 (13)	C10—C21—C22—C23	−177.22 (11)
C5—C4B—C8A—C8	−1.84 (17)	C26—C21—C22—C23	−0.72 (17)
C5—C4B—C8A—C9	178.43 (10)	C10—C21—C26—C25	176.52 (11)
C4B—C5—C6—C7	0.37 (17)	C22—C21—C26—C25	0.08 (16)
C5—C6—C7—C8	−0.71 (18)	C21—C22—C23—C24	0.85 (19)
C6—C7—C8—C8A	−0.22 (17)	C22—C23—C24—C25	−0.3 (2)
C7—C8—C8A—C4B	1.46 (16)	C23—C24—C25—C26	−0.3 (2)
C7—C8—C8A—C9	−178.89 (11)	C24—C25—C26—C21	0.42 (19)
C4B—C8A—C9—N1	−178.85 (12)

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈N₂
M_r	358.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	110
a, b, c (Å)	22.8362 (3), 13.1432 (2), 12.4642 (2)
β (°)	92.874 (1)
V (Å³)	3736.31 (10)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.46 × 0.41 × 0.32

Data collection
Diffractometer	Oxford Xcalibur diffractometer with a Ruby Gemini detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.955, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7177, 3682, 3147
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.102, 1.06
No. of reflections	3682
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20

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

Acknowledgements

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

References

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