3,5-Di­methyl-1,4,7-tri­phenyl-1H,7H-pyrazolo­[3,4-b:4′,3′-e]­pyridine

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

doi:10.1107/S160053680301821X

3,5-Dimethyl-1,4,7-triphenyl-1H,7H-pyrazolo[3,4-b:4',3'-e]pyridine

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

The title compound, C₂₇H₂₁N₅, is isomorphous with 3,5-dimethyl-1,7-diphenyl-4-(2-pyridinyl)-1H,7H-pyrazolo[3,4-b:4',3'-e]pyridine.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301821X/om6159sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301821X/om6159Isup2.hkl Contains datablock I

CCDC reference: 222883

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R factor = 0.040
wR factor = 0.105
Data-to-parameter ratio = 16.2

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 .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 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

The title compound, 3,5-dimethyl-1,4,7-triphenyl-1H,7H-pyrazolo[3,4 − b:4',3'-e]pyridine, (I), is isomorphous with 3,5-dimethyl-1,7-diphenyl-4-(2-pyridinyl)-1H,7H-pyrazolo[3,4 − b:4',3'-e]pyridine, (II) (Low et al., 2003), the only difference being that in (I) a phenyl ring replaces the pyridyl ring of (II).

The bonds and angles for this compound are identical to (II) within 3σ, with the exception of those listed in Table 1.

Experimental top

A mixture of 5-amino-3-methyl-1-phenylpyrazole (10 mmol) and benzaldehyde (20 mmol) was placed into Pyrex-glass open vessels and irradiated in a domestic microwave oven for 1 min (at 600 W). The solid was filtered, washed with ethanol, dried and recrystalized from ethanol. Yield 65%, m.p. 516 K. Analysis calculated for C₂₆H₂₀N₆: C 74.98, H 4.84, N 20.18%; found: C 74.93, H 4.78, N 20.15%.

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.

3,5-Dimethyl-1,4,7-triphenyl-1H,7H-pyrazolo[3,4 − b:4',3'-e]pyridine top

Crystal data top

C₂₇H₂₁N₅	F(000) = 436
M_r = 415.49	D_x = 1.335 Mg m⁻³
Triclinic, P1	Melting point: 516 K
a = 8.5006 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5829 (3) Å	Cell parameters from 4711 reflections
c = 12.4093 (3) Å	θ = 3.1–27.5°
α = 106.0775 (12)°	µ = 0.08 mm⁻¹
β = 97.6152 (15)°	T = 120 K
γ = 100.6751 (10)°	Block, brown
V = 1033.96 (5) Å³	0.40 × 0.26 × 0.20 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	4711 independent reflections
Radiation source: fine-focus sealed X-ray tube	3815 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
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 = −11→10
T_min = 0.968, T_max = 0.984	k = −13→13
21256 measured reflections	l = −16→16

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) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0522P)² + 0.2273P] where P = (F_o² + 2F_c²)/3
4711 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₇H₂₁N₅	γ = 100.6751 (10)°
M_r = 415.49	V = 1033.96 (5) Å³
Triclinic, P1	Z = 2
a = 8.5006 (2) Å	Mo Kα radiation
b = 10.5829 (3) Å	µ = 0.08 mm⁻¹
c = 12.4093 (3) Å	T = 120 K
α = 106.0775 (12)°	0.40 × 0.26 × 0.20 mm
β = 97.6152 (15)°

Data collection top

Nonius KappaCCD diffractometer	4711 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	3815 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.984	R_int = 0.047
21256 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	Δρ_max = 0.21 e Å⁻³
4711 reflections	Δρ_min = −0.21 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	0.31589 (11)	0.07187 (9)	−0.02223 (8)	0.0174 (2)
N2	0.47539 (12)	0.25920 (10)	−0.06321 (8)	0.0186 (2)
N3	0.60853 (12)	0.36576 (9)	−0.00791 (8)	0.0200 (2)
N7	0.21412 (12)	−0.10660 (10)	0.17268 (8)	0.0209 (2)
N8	0.19462 (12)	−0.08908 (9)	0.06531 (8)	0.0182 (2)
C1A	0.43399 (14)	0.18444 (11)	0.00738 (9)	0.0169 (2)
C4	0.64962 (14)	0.36088 (11)	0.09665 (10)	0.0182 (2)
C4A	0.54365 (13)	0.24814 (11)	0.11399 (9)	0.0167 (2)
C5	0.53025 (13)	0.19280 (11)	0.20347 (9)	0.0165 (2)
C5A	0.40630 (14)	0.07551 (11)	0.17696 (9)	0.0170 (2)
C6	0.33836 (14)	−0.01074 (11)	0.23877 (10)	0.0197 (2)
C8A	0.30697 (13)	0.02249 (11)	0.06549 (9)	0.0167 (2)
C21	0.40119 (14)	0.24375 (11)	−0.17647 (9)	0.0186 (2)
C22	0.23732 (15)	0.17973 (12)	−0.21773 (10)	0.0215 (3)
C23	0.16649 (15)	0.16713 (13)	−0.32885 (11)	0.0251 (3)
C24	0.25785 (16)	0.21855 (13)	−0.39858 (10)	0.0260 (3)
C25	0.42140 (16)	0.28241 (13)	−0.35650 (10)	0.0248 (3)
C26	0.49400 (15)	0.29542 (12)	−0.24581 (10)	0.0216 (3)
C41	0.79153 (14)	0.46319 (12)	0.17703 (10)	0.0216 (3)
C51	0.63798 (14)	0.25437 (12)	0.31803 (10)	0.0201 (2)
C52	0.63898 (16)	0.38434 (13)	0.38477 (10)	0.0270 (3)
C53	0.74051 (19)	0.44163 (15)	0.49152 (11)	0.0394 (4)
C54	0.84063 (19)	0.37008 (19)	0.53278 (12)	0.0460 (4)
C55	0.84033 (18)	0.24093 (18)	0.46707 (13)	0.0424 (4)
C56	0.73975 (15)	0.18261 (15)	0.36011 (11)	0.0290 (3)
C61	0.38635 (16)	−0.00210 (13)	0.36103 (10)	0.0262 (3)
C81	0.06502 (14)	−0.17901 (11)	−0.02190 (10)	0.0182 (2)
C82	0.02632 (14)	−0.15679 (12)	−0.12668 (10)	0.0216 (3)
C83	−0.10312 (15)	−0.24664 (12)	−0.20898 (11)	0.0244 (3)
C84	−0.19393 (15)	−0.35728 (13)	−0.18804 (11)	0.0251 (3)
C85	−0.15356 (15)	−0.37876 (12)	−0.08371 (11)	0.0250 (3)
C86	−0.02377 (15)	−0.29142 (12)	−0.00117 (10)	0.0227 (3)
H22	0.1742	0.1448	−0.1703	0.026*
H23	0.0546	0.1230	−0.3574	0.030*
H24	0.2088	0.2101	−0.4744	0.031*
H25	0.4843	0.3176	−0.4040	0.030*
H26	0.6060	0.3392	−0.2175	0.026*
H41A	0.8509	0.5159	0.1352	0.032*
H41B	0.8645	0.4172	0.2114	0.032*
H41C	0.7525	0.5238	0.2373	0.032*
H52	0.5698	0.4340	0.3570	0.032*
H53	0.7410	0.5305	0.5363	0.047*
H54	0.9096	0.4093	0.6061	0.055*
H55	0.9097	0.1917	0.4955	0.051*
H56	0.7402	0.0938	0.3156	0.035*
H61A	0.3046	−0.0662	0.3803	0.039*
H61B	0.3931	0.0899	0.4098	0.039*
H61C	0.4929	−0.0242	0.3734	0.039*
H82	0.0876	−0.0811	−0.1418	0.026*
H83	−0.1297	−0.2320	−0.2806	0.029*
H84	−0.2827	−0.4176	−0.2445	0.030*
H85	−0.2155	−0.4542	−0.0686	0.030*
H86	0.0046	−0.3082	0.0694	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0184 (5)	0.0163 (5)	0.0175 (5)	0.0028 (4)	0.0033 (4)	0.0060 (4)
N2	0.0193 (5)	0.0175 (5)	0.0163 (5)	−0.0011 (4)	0.0000 (4)	0.0061 (4)
N3	0.0194 (5)	0.0169 (5)	0.0203 (5)	−0.0006 (4)	0.0012 (4)	0.0048 (4)
N7	0.0265 (5)	0.0200 (5)	0.0166 (5)	0.0035 (4)	0.0047 (4)	0.0075 (4)
N8	0.0202 (5)	0.0176 (5)	0.0154 (5)	0.0004 (4)	0.0025 (4)	0.0057 (4)
C1A	0.0179 (5)	0.0162 (5)	0.0172 (6)	0.0048 (4)	0.0036 (4)	0.0057 (4)
C4	0.0186 (6)	0.0162 (5)	0.0191 (6)	0.0039 (4)	0.0029 (4)	0.0048 (4)
C4A	0.0168 (5)	0.0153 (5)	0.0171 (6)	0.0039 (4)	0.0024 (4)	0.0039 (4)
C5	0.0174 (5)	0.0156 (5)	0.0167 (6)	0.0062 (4)	0.0031 (4)	0.0037 (4)
C5A	0.0192 (5)	0.0162 (5)	0.0157 (5)	0.0051 (4)	0.0027 (4)	0.0050 (4)
C6	0.0234 (6)	0.0173 (6)	0.0184 (6)	0.0047 (5)	0.0044 (4)	0.0054 (4)
C8A	0.0171 (5)	0.0150 (5)	0.0175 (6)	0.0033 (4)	0.0036 (4)	0.0044 (4)
C21	0.0243 (6)	0.0165 (5)	0.0148 (5)	0.0059 (5)	0.0015 (4)	0.0050 (4)
C22	0.0235 (6)	0.0209 (6)	0.0213 (6)	0.0055 (5)	0.0033 (5)	0.0087 (5)
C23	0.0243 (6)	0.0254 (6)	0.0238 (6)	0.0054 (5)	−0.0011 (5)	0.0075 (5)
C24	0.0332 (7)	0.0279 (7)	0.0179 (6)	0.0109 (5)	0.0009 (5)	0.0079 (5)
C25	0.0324 (7)	0.0249 (6)	0.0203 (6)	0.0089 (5)	0.0080 (5)	0.0092 (5)
C26	0.0230 (6)	0.0206 (6)	0.0210 (6)	0.0041 (5)	0.0038 (5)	0.0072 (5)
C41	0.0212 (6)	0.0189 (6)	0.0214 (6)	0.0000 (5)	0.0018 (5)	0.0052 (5)
C51	0.0185 (5)	0.0228 (6)	0.0175 (6)	−0.0001 (5)	0.0019 (4)	0.0079 (5)
C52	0.0321 (7)	0.0242 (6)	0.0202 (6)	−0.0005 (5)	0.0031 (5)	0.0052 (5)
C53	0.0471 (9)	0.0362 (8)	0.0197 (7)	−0.0124 (7)	0.0028 (6)	0.0009 (6)
C54	0.0344 (8)	0.0681 (12)	0.0209 (7)	−0.0148 (8)	−0.0070 (6)	0.0140 (7)
C55	0.0252 (7)	0.0708 (11)	0.0358 (8)	0.0054 (7)	−0.0031 (6)	0.0319 (8)
C56	0.0240 (6)	0.0382 (8)	0.0288 (7)	0.0077 (5)	0.0032 (5)	0.0175 (6)
C61	0.0335 (7)	0.0251 (6)	0.0181 (6)	0.0014 (5)	0.0037 (5)	0.0080 (5)
C81	0.0168 (5)	0.0176 (6)	0.0182 (6)	0.0034 (4)	0.0035 (4)	0.0030 (4)
C82	0.0214 (6)	0.0194 (6)	0.0229 (6)	0.0017 (5)	0.0034 (5)	0.0073 (5)
C83	0.0239 (6)	0.0246 (6)	0.0218 (6)	0.0037 (5)	−0.0001 (5)	0.0060 (5)
C84	0.0191 (6)	0.0236 (6)	0.0259 (6)	0.0001 (5)	0.0013 (5)	0.0017 (5)
C85	0.0231 (6)	0.0208 (6)	0.0277 (7)	−0.0019 (5)	0.0064 (5)	0.0060 (5)
C86	0.0243 (6)	0.0208 (6)	0.0215 (6)	0.0012 (5)	0.0057 (5)	0.0065 (5)

Geometric parameters (Å, º) top

N1—C1A	1.3337 (15)	C26—H26	0.95
N1—C8A	1.3365 (14)	C41—H41A	0.98
N2—C1A	1.3710 (14)	C41—H41B	0.98
N2—N3	1.3843 (13)	C41—H41C	0.98
N2—C21	1.4141 (14)	C51—C52	1.3931 (18)
N3—C4	1.3161 (15)	C51—C56	1.3932 (17)
N7—C6	1.3152 (15)	C52—C53	1.3877 (18)
N7—N8	1.3881 (13)	C52—H52	0.95
N8—C8A	1.3734 (14)	C53—C54	1.378 (2)
N8—C81	1.4198 (14)	C53—H53	0.95
C1A—C4A	1.4212 (15)	C54—C55	1.383 (3)
C4—C4A	1.4410 (16)	C54—H54	0.95
C4—C41	1.4905 (15)	C55—C56	1.3869 (19)
C4A—C5	1.3992 (16)	C55—H55	0.95
C5—C5A	1.3988 (16)	C56—H56	0.95
C5—C51	1.4850 (16)	C61—H61A	0.98
C5A—C8A	1.4234 (15)	C61—H61B	0.98
C5A—C6	1.4370 (16)	C61—H61C	0.98
C6—C61	1.4906 (16)	C81—C82	1.3924 (16)
C21—C22	1.3895 (16)	C81—C86	1.3926 (16)
C21—C26	1.3937 (16)	C82—C83	1.3909 (16)
C22—C23	1.3893 (17)	C82—H82	0.95
C22—H22	0.95	C83—C84	1.3860 (18)
C23—C24	1.3894 (18)	C83—H83	0.95
C23—H23	0.95	C84—C85	1.3856 (18)
C24—C25	1.3879 (18)	C84—H84	0.95
C24—H24	0.95	C85—C86	1.3853 (16)
C25—C26	1.3877 (17)	C85—H85	0.95
C25—H25	0.95	C86—H86	0.95

C1A—N1—C8A	110.76 (10)	C4—C41—H41A	109.5
C1A—N2—N3	110.76 (9)	C4—C41—H41B	109.5
C1A—N2—C21	129.90 (10)	H41A—C41—H41B	109.5
N3—N2—C21	119.32 (9)	C4—C41—H41C	109.5
C4—N3—N2	107.36 (9)	H41A—C41—H41C	109.5
C6—N7—N8	107.47 (9)	H41B—C41—H41C	109.5
C8A—N8—N7	110.42 (9)	C52—C51—C56	119.11 (11)
C8A—N8—C81	130.92 (10)	C52—C51—C5	120.63 (11)
N7—N8—C81	118.58 (9)	C56—C51—C5	120.26 (11)
N1—C1A—N2	125.31 (10)	C53—C52—C51	120.38 (13)
N1—C1A—C4A	128.02 (10)	C53—C52—H52	119.8
N2—C1A—C4A	106.64 (10)	C51—C52—H52	119.8
N3—C4—C4A	110.74 (10)	C54—C53—C52	120.25 (14)
N3—C4—C41	119.73 (10)	C54—C53—H53	119.9
C4A—C4—C41	129.53 (10)	C52—C53—H53	119.9
C5—C4A—C1A	119.31 (10)	C53—C54—C55	119.74 (13)
C5—C4A—C4	136.18 (10)	C53—C54—H54	120.1
C1A—C4A—C4	104.49 (10)	C55—C54—H54	120.1
C5A—C5—C4A	114.75 (10)	C54—C55—C56	120.60 (14)
C5A—C5—C51	122.54 (10)	C54—C55—H55	119.7
C4A—C5—C51	122.71 (10)	C56—C55—H55	119.7
C5—C5A—C8A	119.52 (10)	C55—C56—C51	119.92 (14)
C5—C5A—C6	135.78 (11)	C55—C56—H56	120.0
C8A—C5A—C6	104.56 (10)	C51—C56—H56	120.0
N7—C6—C5A	110.85 (10)	C6—C61—H61A	109.5
N7—C6—C61	119.64 (10)	C6—C61—H61B	109.5
C5A—C6—C61	129.49 (11)	H61A—C61—H61B	109.5
N1—C8A—N8	125.71 (10)	C6—C61—H61C	109.5
N1—C8A—C5A	127.62 (10)	H61A—C61—H61C	109.5
N8—C8A—C5A	106.65 (10)	H61B—C61—H61C	109.5
C22—C21—C26	120.33 (10)	C82—C81—C86	120.00 (11)
C22—C21—N2	120.54 (10)	C82—C81—N8	121.28 (10)
C26—C21—N2	119.12 (10)	C86—C81—N8	118.72 (10)
C23—C22—C21	119.55 (11)	C83—C82—C81	119.25 (11)
C23—C22—H22	120.2	C83—C82—H82	120.4
C21—C22—H22	120.2	C81—C82—H82	120.4
C22—C23—C24	120.57 (12)	C84—C83—C82	121.02 (11)
C22—C23—H23	119.7	C84—C83—H83	119.5
C24—C23—H23	119.7	C82—C83—H83	119.5
C25—C24—C23	119.42 (11)	C85—C84—C83	119.18 (11)
C25—C24—H24	120.3	C85—C84—H84	120.4
C23—C24—H24	120.3	C83—C84—H84	120.4
C26—C25—C24	120.68 (11)	C86—C85—C84	120.68 (11)
C26—C25—H25	119.7	C86—C85—H85	119.7
C24—C25—H25	119.7	C84—C85—H85	119.7
C25—C26—C21	119.45 (11)	C85—C86—C81	119.85 (11)
C25—C26—H26	120.3	C85—C86—H86	120.1
C21—C26—H26	120.3	C81—C86—H86	120.1

C1A—N2—N3—C4	−1.15 (13)	C5—C5A—C8A—N1	−0.09 (18)
C21—N2—N3—C4	177.31 (10)	C6—C5A—C8A—N1	176.41 (11)
C6—N7—N8—C8A	−1.55 (13)	C5—C5A—C8A—N8	−178.38 (10)
C6—N7—N8—C81	−178.71 (10)	C6—C5A—C8A—N8	−1.87 (12)
C8A—N1—C1A—N2	179.49 (10)	C1A—N2—C21—C22	25.02 (18)
C8A—N1—C1A—C4A	1.64 (16)	N3—N2—C21—C22	−153.10 (11)
N3—N2—C1A—N1	−176.83 (10)	C1A—N2—C21—C26	−155.93 (11)
C21—N2—C1A—N1	4.92 (19)	N3—N2—C21—C26	25.95 (16)
N3—N2—C1A—C4A	1.39 (12)	C26—C21—C22—C23	0.19 (18)
C21—N2—C1A—C4A	−176.86 (11)	N2—C21—C22—C23	179.23 (11)
N2—N3—C4—C4A	0.42 (13)	C21—C22—C23—C24	−0.33 (18)
N2—N3—C4—C41	179.38 (10)	C22—C23—C24—C25	0.28 (19)
N1—C1A—C4A—C5	−1.63 (18)	C23—C24—C25—C26	−0.09 (19)
N2—C1A—C4A—C5	−179.79 (10)	C24—C25—C26—C21	−0.04 (18)
N1—C1A—C4A—C4	177.09 (11)	C22—C21—C26—C25	−0.01 (18)
N2—C1A—C4A—C4	−1.07 (12)	N2—C21—C26—C25	−179.06 (10)
N3—C4—C4A—C5	178.80 (12)	C5A—C5—C51—C52	−117.76 (13)
C41—C4—C4A—C5	0.0 (2)	C4A—C5—C51—C52	61.61 (16)
N3—C4—C4A—C1A	0.41 (13)	C5A—C5—C51—C56	62.32 (16)
C41—C4—C4A—C1A	−178.42 (11)	C4A—C5—C51—C56	−118.31 (13)
C1A—C4A—C5—C5A	0.51 (15)	C56—C51—C52—C53	0.25 (19)
C4—C4A—C5—C5A	−177.70 (12)	C5—C51—C52—C53	−179.68 (12)
C1A—C4A—C5—C51	−178.91 (10)	C51—C52—C53—C54	−0.4 (2)
C4—C4A—C5—C51	2.9 (2)	C52—C53—C54—C55	0.4 (2)
C4A—C5—C5A—C8A	0.22 (15)	C53—C54—C55—C56	−0.2 (2)
C51—C5—C5A—C8A	179.64 (10)	C54—C55—C56—C51	0.1 (2)
C4A—C5—C5A—C6	−174.93 (12)	C52—C51—C56—C55	−0.09 (19)
C51—C5—C5A—C6	4.5 (2)	C5—C51—C56—C55	179.83 (12)
N8—N7—C6—C5A	0.29 (13)	C8A—N8—C81—C82	−4.62 (19)
N8—N7—C6—C61	178.71 (10)	N7—N8—C81—C82	171.84 (10)
C5—C5A—C6—N7	176.63 (12)	C8A—N8—C81—C86	175.19 (11)
C8A—C5A—C6—N7	1.00 (13)	N7—N8—C81—C86	−8.34 (16)
C5—C5A—C6—C61	−1.6 (2)	C86—C81—C82—C83	1.06 (17)
C8A—C5A—C6—C61	−177.22 (12)	N8—C81—C82—C83	−179.13 (11)
C1A—N1—C8A—N8	177.21 (11)	C81—C82—C83—C84	0.17 (18)
C1A—N1—C8A—C5A	−0.77 (16)	C82—C83—C84—C85	−0.57 (19)
N7—N8—C8A—N1	−176.17 (10)	C83—C84—C85—C86	−0.26 (19)
C81—N8—C8A—N1	0.52 (19)	C84—C85—C86—C81	1.49 (19)
N7—N8—C8A—C5A	2.16 (12)	C82—C81—C86—C85	−1.89 (18)
C81—N8—C8A—C5A	178.85 (11)	N8—C81—C86—C85	178.30 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···N1	0.95	2.44	3.0036 (16)	118
C82—H82···N1	0.95	2.31	2.9674 (16)	126
C85—H85···N3ⁱ	0.95	2.54	3.4888 (17)	173

Symmetry code: (i) x−1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₁N₅
M_r	415.49
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.5006 (2), 10.5829 (3), 12.4093 (3)
α, β, γ (°)	106.0775 (12), 97.6152 (15), 100.6751 (10)
V (Å³)	1033.96 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.26 × 0.20

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.968, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	21256, 4711, 3815
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.05
No. of reflections	4711
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

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

C51—C52	1.3931 (18)	C52—C53	1.3877 (18)

N3—C4—C41	119.73 (10)	C53—C52—C51	120.38 (13)
C4A—C4—C41	129.53 (10)	C54—C53—C52	120.25 (14)
C52—C51—C56	119.11 (11)	C53—C54—C55	119.74 (13)
C52—C51—C5	120.63 (11)	C54—C55—C56	120.60 (14)
C56—C51—C5	120.26 (11)	C55—C56—C51	119.92 (14)

C1A—N2—C21—C22	25.02 (18)	C5A—C5—C51—C56	62.32 (16)
N3—N2—C21—C22	−153.10 (11)	C4A—C5—C51—C56	−118.31 (13)
C1A—N2—C21—C26	−155.93 (11)	C8A—N8—C81—C82	−4.62 (19)
N3—N2—C21—C26	25.95 (16)	N7—N8—C81—C82	171.84 (10)
C5A—C5—C51—C52	−117.76 (13)	C8A—N8—C81—C86	175.19 (11)
C4A—C5—C51—C52	61.61 (16)	N7—N8—C81—C86	−8.34 (16)