N,N′-Bis(4-cyano­pyridyl­idene)­benzil dihydrazone

Patra, G.K.; Goldberg, I.

doi:10.1107/S1600536801015768

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N,N'-Bis(4-cyanopyridylidene)benzil dihydrazone

G. K. Patra and I. Goldberg

The title compound, C₃₀H₂₀N₆, was synthesized and its molecular structure was precisely characterized by low-temperature single-crystal analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015768/cv6060sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015768/cv6060Isup2.hkl Contains datablock I

CCDC reference: 175378

checkCIF report

Key indicators

Single-crystal X-ray study
T = 110 K
Mean (C-C) = 0.003 Å
R factor = 0.056
wR factor = 0.154
Data-to-parameter ratio = 17.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.89
         From the CIF: _reflns_number_total               5553
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         5907
         Completeness (_total/calc)             94.01%
          Alert C: < 95% complete

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(23)  -   C(35)  =       1.44 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(30)  -   C(33)  =       1.45 Ang.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     61
                   C31 -C30 -C33 -N34   -17.00 17.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     62
                   C29 -C30 -C33 -N34   163.00 17.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     63
                   C22 -C23 -C35 -N36   123.00  5.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     64
                   C24 -C23 -C35 -N36   -56.00  5.00   1.555   1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 7 Alert Level C = Please check

Comment top

The title compound, (I), is a 1 + 2 Schiff base ligand of benzil dihydrazone and 4-cyano benzaldehyde. It finds a wide range of applications in coordination chemistry owing to its polydentate chelating potential. The imino as well as the nitrilo N atoms can act as donor sites to this end. This compound can also be useful in the supramolecular assembly of hybrid organic–inorganic coordination polymers of varied dimensionality.

Experimental top

1.19 g (5 mmol) of benzil dihydrazone (prepared by Busch & Bailar, 1956) was dissolved in 100 ml of anhydrous methanol. 1.31 g (10 mmol) of solid 4-cyanobenzaldehyde was added to, and dissolved in, this solution with warming. Then, the yellow reaction mixture was refluxed for 8 h, while maintaining dry conditions. The solvent was evaporated to obtain the yellow product. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a dilute acetonitrile solution of this compound. Yield 1.75 g (75%). The product was characterized by elemental analyses and ¹H NMR spectra. Analysis found (calculated): C 77.68 (77.56%), H 4.33 (4.34%), N 18.07 (18.10%). ¹H NMR (200 MHz, CDCl₃, TMS): δ 8.46 (s, 2H), 7.89 (d, J = 8 Hz, 4H), 7.67–7.55 (m, 10H), 7.46 (d, J = 8 Hz, 4H).

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski, 1985); data reduction: DENZO (Otwinowski, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of the title compound. The shown ellipsoids represent displacement parameters at the 50% probability level at 110 K. Geometric parameters of the central part of this molecule include N—N bond lengths of 1.413 (2) and 1.415 (2) Å, N—Csp² bond lengths of 1.275 (2) and 1.277 (2) Å, N—Csp³ bond lengths of 1.285 (2) and 1.289 (2) Å, and an N1—C5—C6—N3 torsion angle of 102.3 (2)°.

Fig. 2. Crystal packing viewed approximately down the a axis (b is horizontal and c is vertical). The contents of two unit cells are shown. The N atoms are indicated by crossed circles. The crystal structure appears to be stabilized by π-stacking between the aryl groups, as well as by dipolar attractions between C—N dipoles of neighboring molecules displaced along c which are arranged in an antiparallel manner with respect to one another.

N,N'-bis(4-cyanopyridylidene)benzil dihydrazone top

Crystal data top

C₃₀H₂₀N₆	F(000) = 484
M_r = 464.52	D_x = 1.252 Mg m⁻³
Triclinic, P1	Melting point: 169-171 deg. C K
a = 9.4430 (3) Å	Mo Kα radiation, λ = 0.71070 Å
b = 10.1390 (3) Å	Cell parameters from 2889 reflections
c = 14.1380 (7) Å	θ = 2.4–27.9°
α = 96.023 (1)°	µ = 0.08 mm⁻¹
β = 95.676 (1)°	T = 110 K
γ = 112.223 (2)°	Prisms, yellow
V = 1231.94 (8) Å³	0.20 × 0.10 × 0.10 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	2889 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 27.9°, θ_min = 2.4°
Detector resolution: 56 microns pixels mm^-1	h = 0→12
1.0° ϕ and ω scans	k = −13→12
8099 measured reflections	l = −18→18
5553 independent 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0728P)²] where P = (F_o² + 2F_c²)/3
5553 reflections	(Δ/σ)_max = 0.016
325 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₃₀H₂₀N₆	γ = 112.223 (2)°
M_r = 464.52	V = 1231.94 (8) Å³
Triclinic, P1	Z = 2
a = 9.4430 (3) Å	Mo Kα radiation
b = 10.1390 (3) Å	µ = 0.08 mm⁻¹
c = 14.1380 (7) Å	T = 110 K
α = 96.023 (1)°	0.20 × 0.10 × 0.10 mm
β = 95.676 (1)°

Data collection top

Nonius KappaCCD diffractometer	2889 reflections with I > 2σ(I)
8099 measured reflections	R_int = 0.054
5553 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 0.97	Δρ_max = 0.25 e Å⁻³
5553 reflections	Δρ_min = −0.27 e Å⁻³
325 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.09241 (18)	0.47137 (17)	0.63095 (12)	0.0288 (4)
N2	0.01691 (19)	0.43526 (18)	0.71168 (12)	0.0298 (4)
N3	−0.07703 (19)	0.11081 (17)	0.58358 (12)	0.0271 (4)
N4	−0.15687 (18)	0.14367 (17)	0.50544 (12)	0.0269 (4)
C5	0.1066 (2)	0.3614 (2)	0.58560 (14)	0.0242 (5)
C6	0.0502 (2)	0.2172 (2)	0.62100 (14)	0.0240 (5)
C7	0.1892 (2)	0.3774 (2)	0.50120 (14)	0.0226 (5)
C8	0.1888 (2)	0.2568 (2)	0.44502 (15)	0.0292 (5)
H8	0.1301	0.1634	0.4587	0.035*
C9	0.2728 (2)	0.2707 (2)	0.36933 (16)	0.0311 (5)
H9	0.2722	0.1871	0.3318	0.037*
C10	0.3573 (2)	0.4049 (2)	0.34783 (16)	0.0337 (5)
H10	0.4157	0.4145	0.2961	0.040*
C11	0.3560 (3)	0.5254 (2)	0.40260 (18)	0.0446 (7)
H11	0.4134	0.6185	0.3880	0.054*
C12	0.2720 (3)	0.5124 (2)	0.47846 (17)	0.0405 (6)
H12	0.2711	0.5962	0.5150	0.049*
C13	0.1474 (2)	0.1960 (2)	0.70246 (15)	0.0254 (5)
C14	0.0837 (3)	0.0877 (2)	0.75691 (16)	0.0382 (6)
H14	−0.0227	0.0259	0.7415	0.046*
C15	0.1745 (3)	0.0692 (3)	0.83375 (18)	0.0444 (6)
H15	0.1296	−0.0026	0.8723	0.053*
C16	0.3304 (3)	0.1560 (2)	0.85367 (16)	0.0379 (6)
H16	0.3935	0.1417	0.9049	0.045*
C17	0.3947 (2)	0.2628 (2)	0.79995 (16)	0.0360 (6)
H17	0.5020	0.3223	0.8140	0.043*
C18	0.3022 (2)	0.2839 (2)	0.72465 (15)	0.0301 (5)
H18	0.3463	0.3593	0.6885	0.036*
C19	−0.0138 (2)	0.5368 (2)	0.75344 (15)	0.0285 (5)
H19	0.0137	0.6258	0.7293	0.034*
C20	−0.0916 (2)	0.5163 (2)	0.83859 (14)	0.0259 (5)
C21	−0.1419 (2)	0.6203 (2)	0.87742 (15)	0.0295 (5)
H21	−0.1197	0.7070	0.8510	0.035*
C22	−0.2241 (2)	0.5979 (2)	0.95421 (15)	0.0313 (5)
H22	−0.2579	0.6691	0.9806	0.038*
C23	−0.2567 (2)	0.4706 (2)	0.99243 (14)	0.0272 (5)
C24	−0.2006 (2)	0.3686 (2)	0.95672 (15)	0.0289 (5)
H24	−0.2197	0.2834	0.9846	0.035*
C25	−0.1178 (2)	0.3924 (2)	0.88112 (14)	0.0271 (5)
H25	−0.0782	0.3241	0.8576	0.033*
C26	−0.2816 (2)	0.0356 (2)	0.46978 (15)	0.0265 (5)
H26	−0.3090	−0.0496	0.4984	0.032*
C27	−0.3827 (2)	0.0396 (2)	0.38662 (14)	0.0248 (5)
C28	−0.3379 (2)	0.1524 (2)	0.33256 (15)	0.0312 (5)
H28	−0.2399	0.2301	0.3505	0.037*
C29	−0.4363 (3)	0.1508 (2)	0.25305 (16)	0.0359 (6)
H29	−0.4054	0.2269	0.2159	0.043*
C30	−0.5817 (2)	0.0368 (2)	0.22710 (15)	0.0337 (5)
C31	−0.6283 (2)	−0.0735 (2)	0.28182 (16)	0.0325 (5)
H31	−0.7279	−0.1494	0.2655	0.039*
C32	−0.5281 (2)	−0.0715 (2)	0.36037 (15)	0.0298 (5)
H32	−0.5592	−0.1478	0.3974	0.036*
C33	−0.6840 (3)	0.0351 (3)	0.14348 (19)	0.0470 (6)
N34	−0.7661 (3)	0.0318 (3)	0.07733 (17)	0.0693 (7)
C35	−0.3506 (2)	0.4399 (2)	1.06825 (16)	0.0318 (5)
N36	−0.4290 (2)	0.4109 (2)	1.12648 (14)	0.0428 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0291 (10)	0.0251 (9)	0.0314 (11)	0.0090 (8)	0.0099 (8)	0.0028 (8)
N2	0.0293 (10)	0.0306 (10)	0.0306 (11)	0.0125 (9)	0.0090 (8)	0.0024 (8)
N3	0.0260 (9)	0.0250 (9)	0.0282 (10)	0.0083 (9)	0.0028 (8)	0.0035 (8)
N4	0.0243 (9)	0.0262 (10)	0.0293 (10)	0.0092 (9)	0.0032 (8)	0.0047 (8)
C5	0.0205 (10)	0.0190 (10)	0.0301 (12)	0.0056 (9)	0.0030 (9)	0.0004 (9)
C6	0.0259 (11)	0.0217 (11)	0.0248 (12)	0.0099 (10)	0.0073 (9)	0.0008 (9)
C7	0.0228 (10)	0.0215 (10)	0.0240 (11)	0.0085 (9)	0.0047 (9)	0.0052 (9)
C8	0.0288 (12)	0.0216 (11)	0.0365 (13)	0.0080 (10)	0.0092 (10)	0.0049 (10)
C9	0.0324 (12)	0.0262 (11)	0.0337 (13)	0.0110 (10)	0.0080 (10)	−0.0004 (10)
C10	0.0362 (13)	0.0341 (13)	0.0358 (14)	0.0155 (11)	0.0161 (11)	0.0102 (11)
C11	0.0577 (16)	0.0259 (12)	0.0565 (17)	0.0148 (12)	0.0335 (14)	0.0158 (11)
C12	0.0522 (15)	0.0229 (12)	0.0489 (16)	0.0131 (12)	0.0260 (13)	0.0059 (11)
C13	0.0259 (11)	0.0235 (11)	0.0270 (12)	0.0102 (10)	0.0061 (9)	0.0002 (9)
C14	0.0343 (13)	0.0350 (13)	0.0390 (15)	0.0065 (11)	−0.0002 (11)	0.0112 (11)
C15	0.0527 (16)	0.0383 (14)	0.0413 (15)	0.0154 (13)	0.0031 (13)	0.0152 (12)
C16	0.0434 (14)	0.0437 (14)	0.0282 (13)	0.0229 (13)	−0.0032 (11)	−0.0014 (11)
C17	0.0275 (12)	0.0415 (13)	0.0336 (14)	0.0117 (11)	−0.0021 (11)	−0.0037 (11)
C18	0.0281 (12)	0.0312 (12)	0.0284 (13)	0.0091 (10)	0.0041 (10)	0.0033 (10)
C19	0.0244 (11)	0.0244 (11)	0.0354 (13)	0.0092 (10)	0.0045 (10)	0.0006 (10)
C20	0.0219 (11)	0.0282 (11)	0.0245 (12)	0.0085 (10)	0.0010 (9)	−0.0015 (9)
C21	0.0308 (12)	0.0289 (11)	0.0312 (13)	0.0142 (10)	0.0057 (10)	0.0042 (10)
C22	0.0320 (12)	0.0339 (12)	0.0313 (13)	0.0183 (11)	0.0045 (10)	−0.0007 (10)
C23	0.0241 (11)	0.0314 (12)	0.0234 (12)	0.0097 (10)	0.0002 (9)	0.0000 (9)
C24	0.0272 (11)	0.0288 (11)	0.0280 (13)	0.0099 (10)	−0.0013 (10)	0.0016 (10)
C25	0.0246 (11)	0.0268 (11)	0.0282 (13)	0.0112 (10)	−0.0009 (10)	−0.0034 (9)
C26	0.0283 (12)	0.0212 (11)	0.0291 (12)	0.0077 (10)	0.0056 (10)	0.0065 (9)
C27	0.0230 (11)	0.0219 (11)	0.0283 (12)	0.0084 (10)	0.0048 (9)	−0.0001 (9)
C28	0.0299 (12)	0.0302 (12)	0.0317 (13)	0.0100 (10)	0.0050 (10)	0.0037 (10)
C29	0.0427 (14)	0.0360 (13)	0.0344 (14)	0.0185 (12)	0.0127 (12)	0.0106 (11)
C30	0.0362 (13)	0.0407 (14)	0.0288 (13)	0.0216 (12)	0.0034 (11)	0.0013 (11)
C31	0.0278 (12)	0.0304 (12)	0.0363 (14)	0.0107 (10)	0.0038 (10)	−0.0033 (10)
C32	0.0323 (12)	0.0233 (11)	0.0319 (13)	0.0102 (10)	0.0026 (10)	0.0014 (9)
C33	0.0445 (15)	0.0578 (17)	0.0410 (16)	0.0232 (14)	0.0038 (13)	0.0081 (13)
N34	0.0575 (15)	0.096 (2)	0.0496 (16)	0.0264 (15)	−0.0070 (13)	0.0201 (14)
C35	0.0319 (12)	0.0310 (12)	0.0315 (14)	0.0128 (11)	0.0012 (11)	0.0021 (10)
N36	0.0489 (13)	0.0456 (12)	0.0425 (13)	0.0243 (11)	0.0144 (11)	0.0149 (10)

Geometric parameters (Å, º) top

N1—C5	1.285 (2)	C18—H18	0.9500
N1—N2	1.413 (2)	C19—C20	1.464 (3)
N2—C19	1.275 (2)	C19—H19	0.9500
N3—C6	1.289 (2)	C20—C21	1.396 (3)
N3—N4	1.415 (2)	C20—C25	1.398 (3)
N4—C26	1.277 (2)	C21—C22	1.385 (3)
C5—C7	1.479 (3)	C21—H21	0.9500
C5—C6	1.514 (3)	C22—C23	1.390 (3)
C6—C13	1.485 (3)	C22—H22	0.9500
C7—C8	1.385 (3)	C23—C24	1.401 (3)
C7—C12	1.386 (3)	C23—C35	1.443 (3)
C8—C9	1.382 (3)	C24—C25	1.374 (3)
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.376 (3)	C25—H25	0.9500
C9—H9	0.9500	C26—C27	1.454 (3)
C10—C11	1.381 (3)	C26—H26	0.9500
C10—H10	0.9500	C27—C32	1.390 (3)
C11—C12	1.384 (3)	C27—C28	1.397 (3)
C11—H11	0.9500	C28—C29	1.380 (3)
C12—H12	0.9500	C28—H28	0.9500
C13—C18	1.376 (3)	C29—C30	1.402 (3)
C13—C14	1.389 (3)	C29—H29	0.9500
C14—C15	1.389 (3)	C30—C31	1.385 (3)
C14—H14	0.9500	C30—C33	1.445 (3)
C15—C16	1.381 (3)	C31—C32	1.379 (3)
C15—H15	0.9500	C31—H31	0.9500
C16—C17	1.373 (3)	C32—H32	0.9500
C16—H16	0.9500	C33—N34	1.143 (3)
C17—C18	1.395 (3)	C35—N36	1.149 (3)
C17—H17	0.9500

C5—N1—N2	111.07 (16)	C17—C18—H18	119.8
C19—N2—N1	113.39 (17)	N2—C19—C20	119.97 (19)
C6—N3—N4	112.50 (16)	N2—C19—H19	120.0
C26—N4—N3	110.75 (16)	C20—C19—H19	120.0
N1—C5—C7	119.85 (18)	C21—C20—C25	119.34 (19)
N1—C5—C6	121.20 (18)	C21—C20—C19	119.96 (19)
C7—C5—C6	118.80 (16)	C25—C20—C19	120.70 (17)
N3—C6—C13	118.08 (17)	C22—C21—C20	120.49 (19)
N3—C6—C5	123.53 (18)	C22—C21—H21	119.8
C13—C6—C5	118.39 (17)	C20—C21—H21	119.8
C8—C7—C12	118.78 (18)	C21—C22—C23	119.48 (18)
C8—C7—C5	120.13 (17)	C21—C22—H22	120.3
C12—C7—C5	121.06 (17)	C23—C22—H22	120.3
C9—C8—C7	120.69 (19)	C22—C23—C24	120.36 (19)
C9—C8—H8	119.7	C22—C23—C35	120.82 (18)
C7—C8—H8	119.7	C24—C23—C35	118.82 (19)
C10—C9—C8	120.54 (19)	C25—C24—C23	119.71 (19)
C10—C9—H9	119.7	C25—C24—H24	120.1
C8—C9—H9	119.7	C23—C24—H24	120.1
C9—C10—C11	119.0 (2)	C24—C25—C20	120.47 (18)
C9—C10—H10	120.5	C24—C25—H25	119.8
C11—C10—H10	120.5	C20—C25—H25	119.8
C10—C11—C12	120.9 (2)	N4—C26—C27	121.78 (18)
C10—C11—H11	119.6	N4—C26—H26	119.1
C12—C11—H11	119.6	C27—C26—H26	119.1
C11—C12—C7	120.12 (19)	C32—C27—C28	119.12 (19)
C11—C12—H12	119.9	C32—C27—C26	119.13 (19)
C7—C12—H12	119.9	C28—C27—C26	121.75 (18)
C18—C13—C14	119.27 (19)	C29—C28—C27	119.9 (2)
C18—C13—C6	120.12 (18)	C29—C28—H28	120.0
C14—C13—C6	120.61 (18)	C27—C28—H28	120.0
C15—C14—C13	120.5 (2)	C28—C29—C30	120.1 (2)
C15—C14—H14	119.7	C28—C29—H29	120.0
C13—C14—H14	119.7	C30—C29—H29	120.0
C16—C15—C14	119.5 (2)	C31—C30—C29	120.3 (2)
C16—C15—H15	120.2	C31—C30—C33	119.8 (2)
C14—C15—H15	120.2	C29—C30—C33	119.9 (2)
C17—C16—C15	120.4 (2)	C32—C31—C30	119.1 (2)
C17—C16—H16	119.8	C32—C31—H31	120.5
C15—C16—H16	119.8	C30—C31—H31	120.5
C16—C17—C18	119.9 (2)	C31—C32—C27	121.5 (2)
C16—C17—H17	120.1	C31—C32—H32	119.2
C18—C17—H17	120.1	C27—C32—H32	119.2
C13—C18—C17	120.4 (2)	N34—C33—C30	179.1 (3)
C13—C18—H18	119.8	N36—C35—C23	177.5 (2)

C5—N1—N2—C19	−173.34 (17)	C6—C13—C18—C17	−178.80 (18)
C6—N3—N4—C26	179.53 (15)	C16—C17—C18—C13	−1.5 (3)
N2—N1—C5—C7	−177.13 (15)	N1—N2—C19—C20	−179.76 (16)
N2—N1—C5—C6	−1.5 (3)	N2—C19—C20—C21	−172.29 (19)
N4—N3—C6—C13	−178.65 (15)	N2—C19—C20—C25	6.9 (3)
N4—N3—C6—C5	0.6 (2)	C25—C20—C21—C22	−3.3 (3)
N1—C5—C6—N3	102.3 (2)	C19—C20—C21—C22	175.93 (18)
C7—C5—C6—N3	−82.1 (2)	C20—C21—C22—C23	−0.2 (3)
N1—C5—C6—C13	−78.5 (2)	C21—C22—C23—C24	3.1 (3)
C7—C5—C6—C13	97.1 (2)	C21—C22—C23—C35	−175.92 (19)
N1—C5—C7—C8	−172.13 (18)	C22—C23—C24—C25	−2.4 (3)
C6—C5—C7—C8	12.2 (3)	C35—C23—C24—C25	176.58 (17)
N1—C5—C7—C12	9.9 (3)	C23—C24—C25—C20	−1.1 (3)
C6—C5—C7—C12	−165.83 (19)	C21—C20—C25—C24	3.9 (3)
C12—C7—C8—C9	1.8 (3)	C19—C20—C25—C24	−175.28 (17)
C5—C7—C8—C9	−176.26 (18)	N3—N4—C26—C27	−178.03 (16)
C7—C8—C9—C10	−0.6 (3)	N4—C26—C27—C32	−169.81 (16)
C8—C9—C10—C11	−0.5 (3)	N4—C26—C27—C28	10.0 (3)
C9—C10—C11—C12	0.4 (3)	C32—C27—C28—C29	−1.4 (3)
C10—C11—C12—C7	0.8 (4)	C26—C27—C28—C29	178.80 (18)
C8—C7—C12—C11	−1.9 (3)	C27—C28—C29—C30	0.7 (3)
C5—C7—C12—C11	176.2 (2)	C28—C29—C30—C31	0.9 (3)
N3—C6—C13—C18	159.06 (18)	C28—C29—C30—C33	−179.67 (19)
C5—C6—C13—C18	−20.2 (3)	C29—C30—C31—C32	−1.8 (3)
N3—C6—C13—C14	−20.8 (3)	C33—C30—C31—C32	178.83 (19)
C5—C6—C13—C14	159.90 (18)	C30—C31—C32—C27	1.0 (3)
C18—C13—C14—C15	0.8 (3)	C28—C27—C32—C31	0.6 (3)
C6—C13—C14—C15	−179.27 (19)	C26—C27—C32—C31	−179.63 (18)
C13—C14—C15—C16	−2.4 (3)	C31—C30—C33—N34	−17 (17)
C14—C15—C16—C17	2.0 (3)	C29—C30—C33—N34	163 (17)
C15—C16—C17—C18	−0.1 (3)	C22—C23—C35—N36	123 (5)
C14—C13—C18—C17	1.1 (3)	C24—C23—C35—N36	−56 (5)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₀N₆
M_r	464.52
Crystal system, space group	Triclinic, P1
Temperature (K)	110
a, b, c (Å)	9.4430 (3), 10.1390 (3), 14.1380 (7)
α, β, γ (°)	96.023 (1), 95.676 (1), 112.223 (2)
V (Å³)	1231.94 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8099, 5553, 2889
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.154, 0.97
No. of reflections	5553
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.27

Computer programs: COLLECT (Nonius, 1999), DENZO (Otwinowski, 1985), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.

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N,N'-Bis(4-cyano­pyridyl­idene)­benzil dihydrazone