3,5-Di­methyl-1,7-di­phenyl-4-(2-pyridyl)-1H,7H-pyrazolo­[3,4-b:4′,3′-e]­pyridine

Low, J.N.; Cobo, J.; Portilla, J.; Quiroga, J.

doi:10.1107/S1600536803018208

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3,5-Dimethyl-1,7-diphenyl-4-(2-pyridyl)-1H,7H-pyrazolo[3,4-b:4′,3′-e]pyridine

J. N. Low, J. Cobo, J. Portilla and J. Quiroga

In the title compound, C₂₆H₂₀N₆, the supramolecular structure is determined by a weak C—H

N hydrogen bond which links the molecules into chains running parallel to [110].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018208/om6158sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018208/om6158Isup2.hkl Contains datablock I

CCDC reference: 222872

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R factor = 0.040
wR factor = 0.110
Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

In our ongoing application of microwave irradiation to heterocyclic synthesis by multicomponent condensation, we have prepared compound (I) from 5-amino-3-methyl-1-phenyl-1H-pyrazole and 2-pyridinecarbadehyde.

There are no unusual bonds and angles in the structure (Fig. 1). The 12-membered fused-ring system defined by atoms N1 to C8A is essentially planar and symmetrical about the N1···C5 line, as shown by the bonds and angles in Table 1. However, the angle of tilt of the phenyl rings out of the plane of the 12-membered ring system varies as is shown by the torsion angles listed in Table 1 so that this symmetry does not extend to the whole molecule. There are two short intramolecular contacts C22—H22··· N1 and C82—H82···N1, i.e. between the two phenyl rings defined by atoms C21–C26 and C81–C86 to atom N1 (Table 2). The C8—H85···N3 weak hydrogen bond links the molecules into C(10) chains (Bernstein et al., 1995) which run parallel to [110] (Fig. 2).

Experimental top

A mixture of 5-amino-3-methyl-1-phenylpyrazole (10 mmol) and 2-pyridinecarbaldehyde (20 mmol) was placed into Pyrex-glass open vessels and irradiated in a domestic microwave oven for 1.5 min (at 600 W). The solid was filtered, washed with ethanol, dried and recrystalized from ethanol. Yield 68%, m.p. 517 K. Analysis calculated for C₂₇H₂₁N₅: C 78.05, H 5.09, N 16.86%; found: C 78.08, H 5.03, N 16.81%.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the C(10) chains running parallel to [110]. The atom labelled with an asterisk (*) is in the molecule at (x − 1, y − 1, z) while that labelled with a hash (#) is in the molecule at (1 + x, 1 + y, z).

3,5-Dimethyl-1,7-diphenyl-4-(2-pyridinyl)-1H,7H-pyrazolo[3,4 − b:4',3'-e]pyridine top

Crystal data top

C₂₆H₂₀N₆	F(000) = 436
M_r = 416.48	D_x = 1.353 Mg m⁻³
Triclinic, P1	Melting point: 517 K
a = 8.4576 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6599 (3) Å	Cell parameters from 4637 reflections
c = 12.3642 (4) Å	θ = 3.1–27.5°
α = 106.9170 (14)°	µ = 0.08 mm⁻¹
β = 98.6240 (16)°	T = 120 K
γ = 100.803 (2)°	Block, brown
V = 1022.48 (5) Å³	0.28 × 0.22 × 0.18 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	4637 independent reflections
Radiation source: fine-focus sealed X-ray tube	3732 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ scans and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −10→10
T_min = 0.977, T_max = 0.985	k = −13→13
19117 measured reflections	l = −16→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0603P)² + 0.1734P] where P = (F_o² + 2F_c²)/3
4637 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₆H₂₀N₆	γ = 100.803 (2)°
M_r = 416.48	V = 1022.48 (5) Å³
Triclinic, P1	Z = 2
a = 8.4576 (2) Å	Mo Kα radiation
b = 10.6599 (3) Å	µ = 0.08 mm⁻¹
c = 12.3642 (4) Å	T = 120 K
α = 106.9170 (14)°	0.28 × 0.22 × 0.18 mm
β = 98.6240 (16)°

Data collection top

Nonius KappaCCD diffractometer	4637 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	3732 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.985	R_int = 0.050
19117 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
4637 reflections	Δρ_min = −0.25 e Å⁻³
291 parameters

Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.31352 (11)	0.06622 (9)	−0.02226 (8)	0.0183 (2)
N2	0.46861 (12)	0.25463 (10)	−0.06259 (8)	0.0197 (2)
N3	0.60148 (12)	0.36471 (10)	−0.00499 (8)	0.0214 (2)
N7	0.22367 (12)	−0.10898 (10)	0.17481 (8)	0.0219 (2)
N8	0.19836 (12)	−0.09346 (10)	0.06625 (8)	0.0194 (2)
N52	0.60600 (13)	0.38270 (11)	0.38405 (9)	0.0257 (2)
C1A	0.43165 (14)	0.18011 (11)	0.00781 (10)	0.0178 (2)
C4	0.64613 (14)	0.36174 (11)	0.10053 (10)	0.0195 (2)
C4A	0.54369 (13)	0.24750 (11)	0.11638 (10)	0.0179 (2)
C5	0.53309 (13)	0.19511 (11)	0.20688 (10)	0.0177 (2)
C5A	0.41189 (14)	0.07542 (11)	0.17944 (9)	0.0181 (2)
C6	0.34921 (14)	−0.01033 (12)	0.24163 (10)	0.0207 (3)
C8A	0.30884 (13)	0.01859 (11)	0.06626 (10)	0.0174 (2)
C21	0.39228 (14)	0.23594 (11)	−0.17791 (10)	0.0196 (2)
C22	0.22943 (15)	0.16217 (12)	−0.22427 (10)	0.0229 (3)
C23	0.15769 (15)	0.14562 (13)	−0.33791 (11)	0.0257 (3)
C24	0.24560 (16)	0.20351 (13)	−0.40458 (11)	0.0267 (3)
C25	0.40694 (16)	0.27891 (13)	−0.35671 (11)	0.0266 (3)
C26	0.48110 (15)	0.29504 (12)	−0.24422 (10)	0.0240 (3)
C41	0.78873 (15)	0.46651 (12)	0.18448 (10)	0.0233 (3)
C51	0.63797 (14)	0.26626 (12)	0.32535 (10)	0.0193 (2)
C53	0.69853 (16)	0.44902 (13)	0.49086 (11)	0.0296 (3)
C54	0.82234 (16)	0.40458 (15)	0.54260 (12)	0.0342 (3)
C55	0.85259 (17)	0.28416 (17)	0.48169 (12)	0.0390 (4)
C56	0.75932 (16)	0.21315 (14)	0.37111 (11)	0.0307 (3)
C61	0.40634 (16)	0.00020 (13)	0.36462 (10)	0.0264 (3)
C81	0.06302 (14)	−0.18390 (11)	−0.02100 (10)	0.0186 (2)
C82	0.01656 (15)	−0.16302 (12)	−0.12590 (10)	0.0223 (3)
C83	−0.12059 (15)	−0.25137 (12)	−0.20700 (11)	0.0242 (3)
C84	−0.21210 (15)	−0.35990 (12)	−0.18481 (11)	0.0245 (3)
C85	−0.16322 (15)	−0.38136 (13)	−0.08105 (11)	0.0258 (3)
C86	−0.02569 (15)	−0.29492 (12)	0.00072 (10)	0.0235 (3)
H22	0.1679	0.1235	−0.1786	0.028*
H23	0.0472	0.0941	−0.3702	0.031*
H24	0.1960	0.1917	−0.4822	0.032*
H25	0.4671	0.3199	−0.4017	0.032*
H26	0.5919	0.3461	−0.2124	0.029*
H41A	0.8357	0.5298	0.1473	0.035*
H41B	0.8729	0.4228	0.2093	0.035*
H41C	0.7513	0.5158	0.2520	0.035*
H53	0.6773	0.5317	0.5334	0.036*
H54	0.8854	0.4556	0.6184	0.041*
H55	0.9366	0.2502	0.5153	0.047*
H56	0.7780	0.1299	0.3275	0.037*
H61A	0.3288	−0.0659	0.3842	0.040*
H61B	0.4119	0.0915	0.4152	0.040*
H61C	0.5160	−0.0180	0.3753	0.040*
H82	0.0781	−0.0889	−0.1420	0.027*
H83	−0.1522	−0.2373	−0.2787	0.029*
H84	−0.3071	−0.4187	−0.2401	0.029*
H85	−0.2245	−0.4561	−0.0656	0.031*
H86	0.0079	−0.3113	0.0712	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0201 (5)	0.0176 (5)	0.0168 (5)	0.0040 (4)	0.0040 (4)	0.0057 (4)
N2	0.0206 (5)	0.0181 (5)	0.0173 (5)	−0.0002 (4)	0.0010 (4)	0.0056 (4)
N3	0.0212 (5)	0.0182 (5)	0.0210 (5)	0.0004 (4)	0.0021 (4)	0.0047 (4)
N7	0.0267 (5)	0.0229 (5)	0.0165 (5)	0.0049 (4)	0.0043 (4)	0.0077 (4)
N8	0.0217 (5)	0.0190 (5)	0.0159 (5)	0.0017 (4)	0.0020 (4)	0.0067 (4)
N52	0.0292 (6)	0.0236 (5)	0.0196 (5)	0.0067 (4)	0.0001 (4)	0.0026 (4)
C1A	0.0179 (5)	0.0172 (5)	0.0182 (6)	0.0047 (4)	0.0038 (4)	0.0055 (4)
C4	0.0192 (6)	0.0178 (6)	0.0203 (6)	0.0043 (5)	0.0038 (4)	0.0048 (4)
C4A	0.0176 (5)	0.0172 (5)	0.0168 (6)	0.0041 (4)	0.0025 (4)	0.0033 (4)
C5	0.0173 (5)	0.0177 (5)	0.0178 (6)	0.0067 (4)	0.0034 (4)	0.0043 (4)
C5A	0.0197 (5)	0.0181 (6)	0.0158 (5)	0.0059 (4)	0.0027 (4)	0.0044 (4)
C6	0.0232 (6)	0.0198 (6)	0.0184 (6)	0.0058 (5)	0.0039 (5)	0.0052 (5)
C8A	0.0178 (5)	0.0167 (5)	0.0174 (5)	0.0048 (4)	0.0040 (4)	0.0045 (4)
C21	0.0246 (6)	0.0183 (6)	0.0157 (6)	0.0070 (5)	0.0019 (4)	0.0054 (4)
C22	0.0239 (6)	0.0240 (6)	0.0222 (6)	0.0057 (5)	0.0042 (5)	0.0099 (5)
C23	0.0228 (6)	0.0275 (6)	0.0243 (6)	0.0061 (5)	−0.0006 (5)	0.0077 (5)
C24	0.0314 (7)	0.0317 (7)	0.0187 (6)	0.0128 (5)	0.0033 (5)	0.0087 (5)
C25	0.0324 (7)	0.0297 (7)	0.0227 (6)	0.0100 (5)	0.0090 (5)	0.0128 (5)
C26	0.0258 (6)	0.0237 (6)	0.0228 (6)	0.0048 (5)	0.0048 (5)	0.0092 (5)
C41	0.0226 (6)	0.0199 (6)	0.0228 (6)	0.0008 (5)	0.0024 (5)	0.0041 (5)
C51	0.0182 (5)	0.0207 (6)	0.0172 (6)	0.0025 (4)	0.0020 (4)	0.0059 (4)
C53	0.0333 (7)	0.0270 (7)	0.0208 (6)	0.0039 (5)	0.0015 (5)	0.0007 (5)
C54	0.0256 (7)	0.0449 (8)	0.0215 (7)	0.0023 (6)	−0.0022 (5)	0.0027 (6)
C55	0.0286 (7)	0.0576 (10)	0.0291 (7)	0.0187 (7)	−0.0036 (6)	0.0115 (7)
C56	0.0293 (7)	0.0355 (7)	0.0261 (7)	0.0149 (6)	0.0015 (5)	0.0058 (6)
C61	0.0325 (7)	0.0274 (7)	0.0177 (6)	0.0037 (5)	0.0034 (5)	0.0081 (5)
C81	0.0178 (5)	0.0181 (5)	0.0172 (6)	0.0040 (4)	0.0034 (4)	0.0024 (4)
C82	0.0243 (6)	0.0199 (6)	0.0210 (6)	0.0027 (5)	0.0033 (5)	0.0065 (5)
C83	0.0253 (6)	0.0246 (6)	0.0205 (6)	0.0057 (5)	0.0012 (5)	0.0064 (5)
C84	0.0201 (6)	0.0235 (6)	0.0238 (6)	0.0023 (5)	0.0028 (5)	0.0015 (5)
C85	0.0250 (6)	0.0222 (6)	0.0263 (6)	−0.0006 (5)	0.0068 (5)	0.0056 (5)
C86	0.0255 (6)	0.0236 (6)	0.0202 (6)	0.0026 (5)	0.0052 (5)	0.0076 (5)

Geometric parameters (Å, º) top

N1—C1A	1.3347 (15)	C25—C26	1.3842 (17)
N1—C8A	1.3364 (15)	C25—H25	0.95
N2—C1A	1.3702 (15)	C26—H26	0.95
N2—N3	1.3879 (13)	C41—H41A	0.98
N2—C21	1.4142 (14)	C41—H41B	0.98
N3—C4	1.3139 (15)	C41—H41C	0.98
N7—C6	1.3147 (15)	C51—C56	1.3871 (17)
N7—N8	1.3896 (13)	C53—C54	1.3753 (19)
N8—C8A	1.3717 (15)	C53—H53	0.95
N8—C81	1.4192 (14)	C54—C55	1.378 (2)
N52—C53	1.3400 (16)	C54—H54	0.95
N52—C51	1.3420 (15)	C55—C56	1.3838 (19)
C1A—C4A	1.4206 (15)	C55—H55	0.95
C4—C4A	1.4375 (16)	C56—H56	0.95
C4—C41	1.4914 (16)	C61—H61A	0.98
C4A—C5	1.3953 (17)	C61—H61B	0.98
C5—C5A	1.3954 (16)	C61—H61C	0.98
C5—C51	1.4898 (15)	C81—C82	1.3908 (16)
C5A—C8A	1.4240 (15)	C81—C86	1.3957 (17)
C5A—C6	1.4345 (17)	C82—C83	1.3893 (16)
C6—C61	1.4894 (16)	C82—H82	0.95
C21—C22	1.3924 (17)	C83—C84	1.3877 (18)
C21—C26	1.3933 (17)	C83—H83	0.95
C22—C23	1.3905 (17)	C84—C85	1.3844 (18)
C22—H22	0.95	C84—H84	0.95
C23—C24	1.3860 (19)	C85—C86	1.3883 (17)
C23—H23	0.95	C85—H85	0.95
C24—C25	1.3886 (18)	C86—H86	0.95
C24—H24	0.95

C1A—N1—C8A	110.97 (9)	C25—C26—H26	120.2
C1A—N2—N3	110.74 (9)	C21—C26—H26	120.2
C1A—N2—C21	130.19 (10)	C4—C41—H41A	109.5
N3—N2—C21	119.06 (9)	C4—C41—H41B	109.5
C4—N3—N2	107.25 (9)	H41A—C41—H41B	109.5
C6—N7—N8	107.25 (10)	C4—C41—H41C	109.5
C8A—N8—N7	110.61 (9)	H41A—C41—H41C	109.5
C8A—N8—C81	130.72 (10)	H41B—C41—H41C	109.5
N7—N8—C81	118.49 (9)	N52—C51—C56	122.88 (11)
C53—N52—C51	117.14 (10)	N52—C51—C5	115.80 (10)
N1—C1A—N2	125.73 (10)	C56—C51—C5	121.31 (10)
N1—C1A—C4A	127.79 (10)	N52—C53—C54	123.90 (12)
N2—C1A—C4A	106.48 (10)	N52—C53—H53	118.0
N3—C4—C4A	110.79 (10)	C54—C53—H53	118.0
N3—C4—C41	120.45 (11)	C53—C54—C55	118.28 (12)
C4A—C4—C41	128.74 (11)	C53—C54—H54	120.9
C5—C4A—C1A	119.31 (10)	C55—C54—H54	120.9
C5—C4A—C4	135.98 (11)	C54—C55—C56	119.28 (12)
C1A—C4A—C4	104.71 (10)	C54—C55—H55	120.4
C5A—C5—C4A	115.03 (10)	C56—C55—H55	120.4
C5A—C5—C51	122.83 (10)	C55—C56—C51	118.50 (12)
C4A—C5—C51	122.07 (10)	C55—C56—H56	120.7
C5—C5A—C8A	119.47 (10)	C51—C56—H56	120.7
C5—C5A—C6	135.71 (11)	C6—C61—H61A	109.5
C8A—C5A—C6	104.67 (10)	C6—C61—H61B	109.5
N7—C6—C5A	110.96 (10)	H61A—C61—H61B	109.5
N7—C6—C61	119.88 (11)	C6—C61—H61C	109.5
C5A—C6—C61	129.15 (11)	H61A—C61—H61C	109.5
N1—C8A—N8	126.07 (10)	H61B—C61—H61C	109.5
N1—C8A—C5A	127.41 (10)	C82—C81—C86	119.88 (11)
N8—C8A—C5A	106.49 (10)	C82—C81—N8	121.49 (10)
C22—C21—C26	120.14 (11)	C86—C81—N8	118.63 (10)
C22—C21—N2	120.76 (11)	C83—C82—C81	119.47 (11)
C26—C21—N2	119.09 (10)	C83—C82—H82	120.3
C23—C22—C21	119.43 (11)	C81—C82—H82	120.3
C23—C22—H22	120.3	C82—C83—C84	121.01 (12)
C21—C22—H22	120.3	C82—C83—H83	119.5
C24—C23—C22	120.73 (12)	C84—C83—H83	119.5
C24—C23—H23	119.6	C85—C84—C83	119.13 (11)
C22—C23—H23	119.6	C85—C84—H84	120.4
C23—C24—C25	119.30 (11)	C83—C84—H84	120.4
C23—C24—H24	120.3	C84—C85—C86	120.74 (12)
C25—C24—H24	120.3	C84—C85—H85	119.6
C26—C25—C24	120.78 (12)	C86—C85—H85	119.6
C26—C25—H25	119.6	C85—C86—C81	119.74 (11)
C24—C25—H25	119.6	C85—C86—H86	120.1
C25—C26—C21	119.60 (11)	C81—C86—H86	120.1

C1A—N2—N3—C4	−1.15 (12)	C5—C5A—C8A—N1	0.62 (17)
C21—N2—N3—C4	178.00 (9)	C6—C5A—C8A—N1	176.81 (11)
C6—N7—N8—C8A	−1.05 (12)	C5—C5A—C8A—N8	−177.32 (10)
C6—N7—N8—C81	−176.71 (9)	C6—C5A—C8A—N8	−1.13 (11)
C8A—N1—C1A—N2	−179.82 (10)	C1A—N2—C21—C22	22.81 (18)
C8A—N1—C1A—C4A	0.72 (16)	N3—N2—C21—C22	−156.16 (10)
N3—N2—C1A—N1	−178.15 (10)	C1A—N2—C21—C26	−158.64 (12)
C21—N2—C1A—N1	2.82 (19)	N3—N2—C21—C26	22.40 (15)
N3—N2—C1A—C4A	1.40 (12)	C26—C21—C22—C23	1.40 (17)
C21—N2—C1A—C4A	−177.63 (10)	N2—C21—C22—C23	179.95 (10)
N2—N3—C4—C4A	0.41 (12)	C21—C22—C23—C24	−1.06 (18)
N2—N3—C4—C41	179.07 (10)	C22—C23—C24—C25	−0.10 (18)
N1—C1A—C4A—C5	−1.56 (17)	C23—C24—C25—C26	0.93 (19)
N2—C1A—C4A—C5	178.90 (10)	C24—C25—C26—C21	−0.58 (18)
N1—C1A—C4A—C4	178.45 (11)	C22—C21—C26—C25	−0.59 (17)
N2—C1A—C4A—C4	−1.09 (11)	N2—C21—C26—C25	−179.16 (10)
N3—C4—C4A—C5	−179.56 (12)	C53—N52—C51—C56	0.71 (19)
C41—C4—C4A—C5	1.9 (2)	C53—N52—C51—C5	−179.94 (11)
N3—C4—C4A—C1A	0.43 (12)	C5A—C5—C51—N52	−108.40 (13)
C41—C4—C4A—C1A	−178.10 (11)	C4A—C5—C51—N52	68.30 (14)
C1A—C4A—C5—C5A	1.72 (15)	C5A—C5—C51—C56	70.95 (16)
C4—C4A—C5—C5A	−178.30 (12)	C4A—C5—C51—C56	−112.34 (14)
C1A—C4A—C5—C51	−175.22 (10)	C51—N52—C53—C54	−0.1 (2)
C4—C4A—C5—C51	4.8 (2)	N52—C53—C54—C55	−0.6 (2)
C4A—C5—C5A—C8A	−1.32 (15)	C53—C54—C55—C56	0.6 (2)
C51—C5—C5A—C8A	175.60 (10)	C54—C55—C56—C51	0.0 (2)
C4A—C5—C5A—C6	−176.03 (12)	N52—C51—C56—C55	−0.7 (2)
C51—C5—C5A—C6	0.9 (2)	C5—C51—C56—C55	180.00 (12)
N8—N7—C6—C5A	0.28 (13)	C8A—N8—C81—C82	−3.78 (18)
N8—N7—C6—C61	179.97 (10)	N7—N8—C81—C82	170.86 (10)
C5—C5A—C6—N7	175.78 (12)	C8A—N8—C81—C86	177.07 (11)
C8A—C5A—C6—N7	0.53 (12)	N7—N8—C81—C86	−8.29 (15)
C5—C5A—C6—C61	−3.9 (2)	C86—C81—C82—C83	1.59 (17)
C8A—C5A—C6—C61	−179.12 (11)	N8—C81—C82—C83	−177.55 (10)
C1A—N1—C8A—N8	177.31 (10)	C81—C82—C83—C84	0.15 (18)
C1A—N1—C8A—C5A	−0.24 (15)	C82—C83—C84—C85	−1.31 (18)
N7—N8—C8A—N1	−176.60 (10)	C83—C84—C85—C86	0.74 (18)
C81—N8—C8A—N1	−1.64 (18)	C84—C85—C86—C81	0.98 (18)
N7—N8—C8A—C5A	1.37 (12)	C82—C81—C86—C85	−2.15 (17)
C81—N8—C8A—C5A	176.34 (11)	N8—C81—C86—C85	177.02 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···N1	0.95	2.43	3.0029 (16)	119
C82—H82···N1	0.95	2.31	2.9721 (16)	126
C85—H85···N3ⁱ	0.95	2.55	3.4922 (18)	173

Symmetry code: (i) x−1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₆
M_r	416.48
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.4576 (2), 10.6599 (3), 12.3642 (4)
α, β, γ (°)	106.9170 (14), 98.6240 (16), 100.803 (2)
V (Å³)	1022.48 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.977, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	19117, 4637, 3732
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.03
No. of reflections	4637
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.25

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2003), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top

N1—C1A	1.3347 (15)	N52—C53	1.3400 (16)
N1—C8A	1.3364 (15)	N52—C51	1.3420 (15)
N2—N3	1.3879 (13)	C1A—C4A	1.4206 (15)
N3—C4	1.3139 (15)	C4—C4A	1.4375 (16)
N7—C6	1.3147 (15)	C4A—C5	1.3953 (17)
N7—N8	1.3896 (13)	C5—C5A	1.3954 (16)
N8—C8A	1.3717 (15)	C5A—C8A	1.4240 (15)

C1A—N1—C8A	110.97 (9)	C5A—C5—C4A	115.03 (10)
C1A—N2—N3	110.74 (9)	C5A—C5—C51	122.83 (10)
C1A—N2—C21	130.19 (10)	C4A—C5—C51	122.07 (10)
N3—N2—C21	119.06 (9)	C5—C5A—C8A	119.47 (10)
C4—N3—N2	107.25 (9)	C5—C5A—C6	135.71 (11)
C6—N7—N8	107.25 (10)	C8A—C5A—C6	104.67 (10)
C8A—N8—N7	110.61 (9)	N7—C6—C5A	110.96 (10)
C8A—N8—C81	130.72 (10)	N7—C6—C61	119.88 (11)
N7—N8—C81	118.49 (9)	C5A—C6—C61	129.15 (11)
C53—N52—C51	117.14 (10)	N1—C8A—N8	126.07 (10)
N1—C1A—N2	125.73 (10)	N1—C8A—C5A	127.41 (10)
N1—C1A—C4A	127.79 (10)	N8—C8A—C5A	106.49 (10)
N2—C1A—C4A	106.48 (10)	N52—C51—C56	122.88 (11)
N3—C4—C4A	110.79 (10)	N52—C51—C5	115.80 (10)
N3—C4—C41	120.45 (11)	N52—C53—C54	123.90 (12)
C4A—C4—C41	128.74 (11)	C53—C54—C55	118.28 (12)
C5—C4A—C1A	119.31 (10)	C54—C55—C56	119.28 (12)
C5—C4A—C4	135.98 (11)	C55—C56—C51	118.50 (12)
C1A—C4A—C4	104.71 (10)

C1A—N2—C21—C22	22.81 (18)	C5A—C5—C51—C56	70.95 (16)
N3—N2—C21—C22	−156.16 (10)	C4A—C5—C51—C56	−112.34 (14)
C1A—N2—C21—C26	−158.64 (12)	C8A—N8—C81—C82	−3.78 (18)
N3—N2—C21—C26	22.40 (15)	N7—N8—C81—C82	170.86 (10)
C5A—C5—C51—N52	−108.40 (13)	C8A—N8—C81—C86	177.07 (11)
C4A—C5—C51—N52	68.30 (14)	N7—N8—C81—C86	−8.29 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···N1	0.95	2.43	3.0029 (16)	119
C82—H82···N1	0.95	2.31	2.9721 (16)	126
C85—H85···N3ⁱ	0.95	2.55	3.4922 (18)	173

Symmetry code: (i) x−1, y−1, z.

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