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

Dumitru, F.; Şerb, M.-D.; Englert, U.

doi:10.1107/S1600536811011238

organic compounds

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Volume 67| Part 5| May 2011| Page o1030

doi:10.1107/S1600536811011238

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

Florina Dumitru,^a Mihaela-Diana Şerb ^a and Ulli Englert ^b ^*

^aFaculty of Applied Chemistry and Materials Science, University Politehnica of Bucharest, Polizu 1, RO-011061 Bucharest, Romania, and ^bInstitut für Anorganische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
^*Correspondence e-mail: ullrich.englert@ac.rwth-aachen.de

(Received 23 March 2011; accepted 25 March 2011; online 7 April 2011)

The title compound, C₃₃H₂₅N₅, 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 molecules 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_r = 491.58
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.117
S = 1.04
5391 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 1999 ); data reduction: SAINT-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.

Supporting information

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

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

checkCIF report

Comment top

The title compound is structurally related to terpyridyl (unsaturated nitrogen donor group incorporated into a tridentate frame) and offers a terpyridine-like coordination environment through a highly efficient and simple ligand synthesis. Analogously to terpyridine-ligands which exhibit all-trans transoid configurations about the interannular carbon-carbon bonds in order to minimize electrostatic interactions between the nitrogen lone pairs (Fallahpour, 2003; Constable, 2007), pyridine-2,6-dicarboxaldehydebis(benzophenone hydrazone) presents a transoid conformation for the (–N═C–C═N–C–C═N–) moiety wherein the lone-pair electrons of adjacent N atoms are directed away from each other. The dihedral angle formed by the phenyl rings attached to C7 is 69.67 (9)° and the dihedral angle formed by the phenyl rings attached to C21 is 66.23 (9)°. The shortest distance between the centroids of aromatic rings in neighbouring molecules amounts to 3.8080 (14) Å [Cg(1)-Cg(3)ⁱ; ring (1): N1-C3-C2-C1-C4-C5; ring (3): C14-C15-C16-C17-C18-C19; symmetry operator (i): 1-x, 1-y, 1-z].

Related literature top

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 top

pyridine-2,6-dicarboxaldehyde has been prepared according to the procedure of Vance et al. (1998) by oxidation of 2,6-pyridinemethanol with activated manganese(IV) dioxide. pyridine-2,6-dicarboxaldehydebis(benzophenone hydrazone) has been synthesized by condensation of one equivalent of pyridine-2,6-dicarboxaldehyde (0.135 g, 1 mmol) with two equivalents of benzophenone hydrazone (0.392 g, 2 mmol) in MeOH (40 ml) with stirring under reflux for 2 h. After solvent evaporation, the resulting crude material was recrystallized from acetonitrile to give the title compound as yellow crystals. ¹H-NMR (400 Hz, CD₃CN, p.p.m.): δ 8.413 (s, 2H, CH═N), 7.717 (br, 3H, H^py), 7.692 (m, 2H, H^ar), 7.674–7.671 (d, 2H, H^ar), 7.511–7.498 (t, 1H, H^ar), 7.489–7.482 (t, 1H, H^ar), 7.460–7.454 (d, 5H, H^ar), 7.446–7.442 (d, 5H, H^ar), 7.325–7.320 (d, 2H, H^ar), 7.312–7.301 (d, 2H, H^ar).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

Fig. 1. : PLATON (Spek, 2009) plot with displacement ellipsoids at 50% probability; H atoms are represented by spheres of arbitrary radius.

2,6-bis({[2-(diphenylmethylidene)hydrazin-1-ylidene]methyl})pyridine top

Crystal data top

C₃₃H₂₅N₅	F(000) = 2064
M_r = 491.58	D_x = 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

Data collection top

Bruker SMART APEX CCD diffractometer	5391 independent reflections
Radiation source: fine-focus sealed tube	3723 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ω scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −29→29
T_min = 0.971, T_max = 0.994	k = −15→15
30994 measured reflections	l = −23→23

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0352P)² + 2.9488P] where P = (F_o² + 2F_c²)/3
5391 reflections	(Δ/σ)_max = 0.001
343 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₃H₂₅N₅	V = 5255.3 (19) Å³
M_r = 491.58	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.702 (5) Å	µ = 0.08 mm⁻¹
b = 12.344 (3) Å	T = 100 K
c = 18.758 (4) Å	0.40 × 0.17 × 0.08 mm
β = 106.742 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	5391 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3723 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.994	R_int = 0.090
30994 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
5391 reflections	Δρ_min = −0.21 e Å⁻³
343 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	0.61026 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₃₃H₂₅N₅
M_r	491.58
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	23.702 (5), 12.344 (3), 18.758 (4)
β (°)	106.742 (4)
V (Å³)	5255.3 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.17 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.971, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	30994, 5391, 3723
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.117, 1.04
No. of reflections	5391
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Acknowledgements

The authors recognize financial support from the European Social Fund through POSDRU/89/1.5/S/54785 project: `Postdoctoral Program for Advanced Research in the field of nanomaterials'.

References

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