Pyridine-2,6-dicarboxaldehyde bis[(diphenylmethylidene)hydrazone].

The title compound, C(33)H(25)N(5), belongs to the family of pyridine-2,6-dicarboxaldehyde Schiff bases which possess a terdentate coordinating site (-N=C-C=N-C-C=N-) similar to terpyridine derivatives. The dihedral angles between pairs of terminal rings are 69.67 (9) and 66.23 (9)°. The shortest distance between the centroids of aromatic rings in neighbouring mol-ecules is 3.8080 (14) Å.

Related literature

For compounds containing the (–N=C–C=N–C–C=N–) moiety in acyclic ligands, see: Vance et al. (1998 ▶); Albrecht et al. (2007 ▶) and in macrocyclic ligands, see: Haussmann et al. (2007 ▶); Plattner et al. (2002 ▶). For electrostatic inter­actions between the nitro­gen lone pairs, which determine the all-trans transoid solid-state configuration of the archetypal terpyridine ligand, see: Fallahpour (2003 ▶); Constable (2007 ▶).

Experimental

Crystal data

C33H25N5

M = 491.58

Monoclinic,

a = 23.702 (5) Å

b = 12.344 (3) Å

c = 18.758 (4) Å

β = 106.742 (4)°

V = 5255.3 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.40 × 0.17 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.971, T max = 0.994

30994 measured reflections

5391 independent reflections

3723 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.117

S = 1.04

5391 reflections

343 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAIn class="Chemical">NT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011238/bt5500sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011238/bt5500Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C33H25N5	F(000) = 2064
Mr = 491.58	Dx = 1.243 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1380 reflections
a = 23.702 (5) Å	θ = 2.3–20.1°
b = 12.344 (3) Å	µ = 0.08 mm−1
c = 18.758 (4) Å	T = 100 K
β = 106.742 (4)°	Fragment, yellow
V = 5255.3 (19) Å3	0.40 × 0.17 × 0.08 mm
Z = 8

Bruker SMART APEX CCD diffractometer	5391 independent reflections
Radiation source: fine-focus sealed tube	3723 reflections with I > 2σ(I)
graphite	Rint = 0.090
ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −29→29
Tmin = 0.971, Tmax = 0.994	k = −15→15
30994 measured reflections	l = −23→23

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0352P)2 + 2.9488P] where P = (Fo2 + 2Fc2)/3
5391 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.61026 (7)	0.42994 (12)	0.40175 (8)	0.0224 (4)
N2	0.48535 (6)	0.36138 (12)	0.46057 (8)	0.0234 (4)
N3	0.42988 (6)	0.41191 (12)	0.44402 (8)	0.0230 (4)
N4	0.75138 (7)	0.44728 (13)	0.37188 (9)	0.0250 (4)
N5	0.77596 (7)	0.53493 (13)	0.34311 (9)	0.0253 (4)
C1	0.65304 (8)	0.23302 (16)	0.46965 (11)	0.0276 (5)
H1	0.6677	0.1664	0.4931	0.033*
C2	0.68692 (8)	0.29596 (15)	0.43668 (10)	0.0260 (4)
H2	0.7249	0.2723	0.4358	0.031*
C3	0.66450 (8)	0.39407 (15)	0.40490 (10)	0.0218 (4)
C4	0.59769 (8)	0.26889 (15)	0.46784 (10)	0.0246 (4)
H4	0.5735	0.2273	0.4900	0.029*
C5	0.57755 (8)	0.36729 (15)	0.43294 (10)	0.0214 (4)
C6	0.51856 (8)	0.40877 (15)	0.42733 (10)	0.0219 (4)
H6	0.5048	0.4718	0.3986	0.026*
C7	0.39333 (8)	0.36647 (14)	0.47450 (10)	0.0207 (4)
C8	0.40803 (7)	0.26922 (14)	0.52396 (10)	0.0204 (4)
C9	0.40873 (8)	0.27596 (16)	0.59825 (10)	0.0254 (4)
H9	0.3990	0.3423	0.6174	0.031*
C10	0.42363 (8)	0.18627 (17)	0.64447 (11)	0.0307 (5)
H10	0.4245	0.1918	0.6953	0.037*
C11	0.43716 (9)	0.08927 (16)	0.61696 (11)	0.0303 (5)
H11	0.4474	0.0280	0.6487	0.036*
C12	0.43578 (8)	0.08137 (16)	0.54286 (11)	0.0279 (5)
H12	0.4445	0.0142	0.5236	0.033*
C13	0.42185 (8)	0.17068 (15)	0.49684 (11)	0.0249 (4)
H13	0.4217	0.1649	0.4463	0.030*
C14	0.33326 (8)	0.41441 (14)	0.45463 (10)	0.0209 (4)
C15	0.32071 (8)	0.50628 (15)	0.40943 (10)	0.0256 (4)
H15	0.3512	0.5399	0.3939	0.031*
C16	0.26442 (9)	0.54899 (16)	0.38698 (11)	0.0287 (5)
H16	0.2564	0.6111	0.3558	0.034*
C17	0.21974 (9)	0.50112 (16)	0.40998 (11)	0.0289 (5)
H17	0.1810	0.5301	0.3942	0.035*
C18	0.23155 (8)	0.41164 (16)	0.45561 (12)	0.0299 (5)
H18	0.2010	0.3796	0.4720	0.036*
C19	0.28792 (8)	0.36812 (15)	0.47775 (11)	0.0265 (4)
H19	0.2957	0.3061	0.5090	0.032*
C20	0.69872 (8)	0.46825 (15)	0.37254 (10)	0.0239 (4)
H20	0.6811	0.5343	0.3513	0.029*
C21	0.82136 (8)	0.51081 (15)	0.32125 (9)	0.0209 (4)
C22	0.84387 (8)	0.39924 (15)	0.31789 (10)	0.0211 (4)
C23	0.90133 (8)	0.37120 (16)	0.35746 (10)	0.0267 (4)
H23	0.9265	0.4241	0.3873	0.032*
C24	0.92223 (9)	0.26719 (16)	0.35387 (11)	0.0313 (5)
H24	0.9611	0.2484	0.3820	0.038*
C25	0.88609 (9)	0.19091 (17)	0.30904 (12)	0.0339 (5)
H25	0.9004	0.1197	0.3059	0.041*
C26	0.82924 (9)	0.21799 (16)	0.26881 (12)	0.0340 (5)
H26	0.8046	0.1655	0.2378	0.041*
C27	0.80817 (8)	0.32135 (16)	0.27363 (11)	0.0277 (5)
H27	0.7689	0.3392	0.2464	0.033*
C28	0.85117 (8)	0.60294 (15)	0.29616 (10)	0.0220 (4)
C29	0.83879 (8)	0.71002 (15)	0.31126 (10)	0.0246 (4)
H29	0.8104	0.7240	0.3370	0.030*
C30	0.86733 (9)	0.79540 (16)	0.28925 (10)	0.0282 (5)
H30	0.8583	0.8676	0.2997	0.034*
C31	0.90906 (9)	0.77644 (17)	0.25204 (10)	0.0309 (5)
H31	0.9294	0.8353	0.2380	0.037*
C32	0.92088 (9)	0.67150 (17)	0.23551 (11)	0.0318 (5)
H32	0.9488	0.6583	0.2089	0.038*
C33	0.89241 (8)	0.58532 (16)	0.25738 (10)	0.0273 (4)
H33	0.9011	0.5134	0.2458	0.033*

	U11	U22	U33	U12	U13	U23
N1	0.0201 (8)	0.0261 (9)	0.0225 (8)	0.0002 (7)	0.0088 (7)	0.0003 (7)
N2	0.0173 (8)	0.0262 (9)	0.0276 (9)	0.0014 (7)	0.0079 (7)	−0.0006 (7)
N3	0.0173 (8)	0.0247 (9)	0.0277 (9)	0.0011 (7)	0.0075 (7)	−0.0011 (7)
N4	0.0230 (9)	0.0262 (9)	0.0297 (9)	0.0000 (7)	0.0136 (7)	0.0020 (7)
N5	0.0226 (9)	0.0271 (9)	0.0296 (9)	−0.0010 (7)	0.0128 (7)	0.0028 (7)
C1	0.0253 (11)	0.0254 (11)	0.0325 (11)	0.0033 (9)	0.0090 (9)	0.0058 (9)
C2	0.0201 (10)	0.0312 (11)	0.0286 (10)	0.0038 (8)	0.0102 (8)	0.0016 (8)
C3	0.0182 (10)	0.0273 (11)	0.0213 (9)	0.0016 (8)	0.0078 (8)	−0.0014 (8)
C4	0.0223 (10)	0.0266 (11)	0.0275 (10)	0.0002 (8)	0.0114 (8)	0.0030 (8)
C5	0.0194 (10)	0.0257 (10)	0.0201 (9)	−0.0015 (8)	0.0070 (8)	−0.0018 (8)
C6	0.0204 (10)	0.0234 (10)	0.0227 (10)	0.0007 (8)	0.0076 (8)	0.0010 (8)
C7	0.0190 (9)	0.0208 (10)	0.0231 (10)	−0.0029 (8)	0.0072 (8)	−0.0041 (8)
C8	0.0128 (9)	0.0237 (10)	0.0255 (10)	−0.0016 (7)	0.0069 (8)	0.0000 (8)
C9	0.0220 (10)	0.0277 (11)	0.0297 (11)	0.0039 (8)	0.0124 (8)	−0.0004 (8)
C10	0.0286 (11)	0.0417 (13)	0.0264 (11)	0.0061 (10)	0.0153 (9)	0.0065 (9)
C11	0.0279 (11)	0.0315 (12)	0.0351 (12)	0.0041 (9)	0.0148 (9)	0.0103 (9)
C12	0.0249 (11)	0.0228 (11)	0.0381 (12)	0.0023 (8)	0.0127 (9)	0.0003 (9)
C13	0.0215 (10)	0.0278 (11)	0.0258 (10)	−0.0007 (8)	0.0073 (8)	−0.0014 (8)
C14	0.0210 (10)	0.0197 (10)	0.0227 (10)	0.0008 (8)	0.0073 (8)	−0.0038 (8)
C15	0.0224 (10)	0.0270 (11)	0.0295 (10)	0.0004 (8)	0.0107 (8)	0.0021 (8)
C16	0.0284 (11)	0.0256 (11)	0.0318 (11)	0.0052 (9)	0.0083 (9)	0.0050 (9)
C17	0.0185 (10)	0.0296 (11)	0.0370 (12)	0.0050 (8)	0.0054 (9)	−0.0023 (9)
C18	0.0182 (10)	0.0277 (11)	0.0462 (13)	−0.0004 (8)	0.0130 (9)	0.0020 (9)
C19	0.0197 (10)	0.0235 (10)	0.0366 (11)	−0.0006 (8)	0.0085 (9)	0.0037 (9)
C20	0.0216 (10)	0.0265 (10)	0.0261 (10)	0.0032 (8)	0.0110 (8)	0.0015 (8)
C21	0.0168 (9)	0.0275 (10)	0.0188 (9)	−0.0010 (8)	0.0059 (7)	−0.0007 (8)
C22	0.0199 (10)	0.0249 (10)	0.0218 (9)	−0.0005 (8)	0.0115 (8)	0.0008 (8)
C23	0.0241 (10)	0.0328 (11)	0.0249 (10)	0.0009 (9)	0.0096 (8)	−0.0005 (8)
C24	0.0269 (11)	0.0374 (12)	0.0326 (11)	0.0109 (9)	0.0135 (9)	0.0087 (9)
C25	0.0422 (13)	0.0255 (11)	0.0448 (13)	0.0059 (10)	0.0297 (11)	0.0063 (10)
C26	0.0335 (12)	0.0293 (12)	0.0456 (13)	−0.0081 (9)	0.0218 (10)	−0.0095 (10)
C27	0.0199 (10)	0.0310 (11)	0.0344 (11)	−0.0040 (9)	0.0113 (9)	−0.0047 (9)
C28	0.0167 (9)	0.0285 (11)	0.0202 (9)	−0.0028 (8)	0.0043 (8)	−0.0005 (8)
C29	0.0220 (10)	0.0293 (11)	0.0221 (10)	0.0007 (8)	0.0057 (8)	0.0007 (8)
C30	0.0311 (11)	0.0255 (11)	0.0245 (10)	−0.0009 (9)	0.0026 (9)	0.0023 (8)
C31	0.0303 (11)	0.0359 (12)	0.0248 (10)	−0.0098 (9)	0.0050 (9)	0.0050 (9)
C32	0.0283 (11)	0.0408 (13)	0.0300 (11)	−0.0060 (9)	0.0140 (9)	−0.0004 (9)
C33	0.0248 (11)	0.0303 (11)	0.0289 (11)	−0.0018 (9)	0.0111 (9)	−0.0022 (9)

N1—C5	1.343 (2)	C15—H15	0.95
N1—C3	1.345 (2)	C16—C17	1.385 (3)
N2—C6	1.278 (2)	C16—H16	0.95
N2—N3	1.407 (2)	C17—C18	1.376 (3)
N3—C7	1.295 (2)	C17—H17	0.95
N4—C20	1.278 (2)	C18—C19	1.388 (3)
N4—N5	1.408 (2)	C18—H18	0.95
N5—C21	1.292 (2)	C19—H19	0.95
C1—C4	1.376 (3)	C20—H20	0.95
C1—C2	1.385 (3)	C21—C22	1.485 (3)
C1—H1	0.95	C21—C28	1.485 (3)
C2—C3	1.386 (3)	C22—C27	1.387 (3)
C2—H2	0.95	C22—C23	1.394 (3)
C3—C20	1.466 (3)	C23—C24	1.385 (3)
C4—C5	1.397 (3)	C23—H23	0.95
C4—H4	0.95	C24—C25	1.383 (3)
C5—C6	1.464 (2)	C24—H24	0.95
C6—H6	0.95	C25—C26	1.383 (3)
C7—C14	1.487 (2)	C25—H25	0.95
C7—C8	1.496 (2)	C26—C27	1.383 (3)
C8—C9	1.391 (3)	C26—H26	0.95
C8—C13	1.393 (3)	C27—H27	0.95
C9—C10	1.388 (3)	C28—C33	1.393 (3)
C9—H9	0.95	C28—C29	1.400 (3)
C10—C11	1.378 (3)	C29—C30	1.378 (3)
C10—H10	0.95	C29—H29	0.95
C11—C12	1.384 (3)	C30—C31	1.385 (3)
C11—H11	0.95	C30—H30	0.95
C12—C13	1.380 (3)	C31—C32	1.379 (3)
C12—H12	0.95	C31—H31	0.95
C13—H13	0.95	C32—C33	1.384 (3)
C14—C19	1.392 (3)	C32—H32	0.95
C14—C15	1.396 (3)	C33—H33	0.95
C15—C16	1.383 (3)
C5—N1—C3	117.13 (16)	C17—C16—H16	120.0
C6—N2—N3	110.94 (15)	C18—C17—C16	119.95 (18)
C7—N3—N2	114.33 (15)	C18—C17—H17	120.0
C20—N4—N5	111.17 (15)	C16—C17—H17	120.0
C21—N5—N4	114.78 (15)	C17—C18—C19	120.17 (19)
C4—C1—C2	118.69 (18)	C17—C18—H18	119.9
C4—C1—H1	120.7	C19—C18—H18	119.9
C2—C1—H1	120.7	C18—C19—C14	120.72 (18)
C1—C2—C3	118.84 (18)	C18—C19—H19	119.6
C1—C2—H2	120.6	C14—C19—H19	119.6
C3—C2—H2	120.6	N4—C20—C3	122.41 (17)
N1—C3—C2	123.35 (17)	N4—C20—H20	118.8
N1—C3—C20	114.35 (16)	C3—C20—H20	118.8
C2—C3—C20	122.30 (17)	N5—C21—C22	124.72 (17)
C1—C4—C5	119.08 (18)	N5—C21—C28	116.10 (16)
C1—C4—H4	120.5	C22—C21—C28	119.16 (16)
C5—C4—H4	120.5	C27—C22—C23	118.72 (18)
N1—C5—C4	122.86 (17)	C27—C22—C21	120.22 (17)
N1—C5—C6	115.26 (16)	C23—C22—C21	121.04 (17)
C4—C5—C6	121.88 (17)	C24—C23—C22	120.84 (19)
N2—C6—C5	120.97 (17)	C24—C23—H23	119.6
N2—C6—H6	119.5	C22—C23—H23	119.6
C5—C6—H6	119.5	C25—C24—C23	119.56 (19)
N3—C7—C14	115.53 (16)	C25—C24—H24	120.2
N3—C7—C8	123.75 (16)	C23—C24—H24	120.2
C14—C7—C8	120.66 (15)	C26—C25—C24	120.19 (19)
C9—C8—C13	118.80 (17)	C26—C25—H25	119.9
C9—C8—C7	120.45 (16)	C24—C25—H25	119.9
C13—C8—C7	120.75 (16)	C25—C26—C27	120.07 (19)
C10—C9—C8	120.36 (18)	C25—C26—H26	120.0
C10—C9—H9	119.8	C27—C26—H26	120.0
C8—C9—H9	119.8	C26—C27—C22	120.60 (19)
C11—C10—C9	120.28 (18)	C26—C27—H27	119.7
C11—C10—H10	119.9	C22—C27—H27	119.7
C9—C10—H10	119.9	C33—C28—C29	118.18 (17)
C10—C11—C12	119.77 (18)	C33—C28—C21	121.01 (17)
C10—C11—H11	120.1	C29—C28—C21	120.81 (17)
C12—C11—H11	120.1	C30—C29—C28	120.78 (18)
C13—C12—C11	120.26 (18)	C30—C29—H29	119.6
C13—C12—H12	119.9	C28—C29—H29	119.6
C11—C12—H12	119.9	C29—C30—C31	120.34 (19)
C12—C13—C8	120.52 (18)	C29—C30—H30	119.8
C12—C13—H13	119.7	C31—C30—H30	119.8
C8—C13—H13	119.7	C32—C31—C30	119.52 (19)
C19—C14—C15	118.32 (17)	C32—C31—H31	120.2
C19—C14—C7	121.87 (16)	C30—C31—H31	120.2
C15—C14—C7	119.78 (17)	C31—C32—C33	120.49 (19)
C16—C15—C14	120.84 (18)	C31—C32—H32	119.8
C16—C15—H15	119.6	C33—C32—H32	119.8
C14—C15—H15	119.6	C32—C33—C28	120.67 (19)
C15—C16—C17	119.98 (18)	C32—C33—H33	119.7
C15—C16—H16	120.0	C28—C33—H33	119.7