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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301821X/om6159sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301821X/om6159Isup2.hkl
Contains datablock I

CCDC reference: 222883

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](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%.

Refinement top

Molecule (I) crystallized in the triclinic system; space group P1 was assumed and confirmed by the analysis. H atoms were treated as riding atoms, with C—H 0.95 Å (aromatic) and 0.98 Å (methyl).

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
[Figure 1] 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
C27H21N5F(000) = 436
Mr = 415.49Dx = 1.335 Mg m3
Triclinic, P1Melting point: 516 K
a = 8.5006 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.5829 (3) ÅCell parameters from 4711 reflections
c = 12.4093 (3) Åθ = 3.1–27.5°
α = 106.0775 (12)°µ = 0.08 mm1
β = 97.6152 (15)°T = 120 K
γ = 100.6751 (10)°Block, brown
V = 1033.96 (5) Å30.40 × 0.26 × 0.20 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
4711 independent reflections
Radiation source: fine-focus sealed X-ray tube3815 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ϕ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1110
Tmin = 0.968, Tmax = 0.984k = 1313
21256 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0522P)2 + 0.2273P]
where P = (Fo2 + 2Fc2)/3
4711 reflections(Δ/σ)max < 0.001
291 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C27H21N5γ = 100.6751 (10)°
Mr = 415.49V = 1033.96 (5) Å3
Triclinic, P1Z = 2
a = 8.5006 (2) ÅMo Kα radiation
b = 10.5829 (3) ŵ = 0.08 mm1
c = 12.4093 (3) ÅT = 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)
Tmin = 0.968, Tmax = 0.984Rint = 0.047
21256 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.05Δρmax = 0.21 e Å3
4711 reflectionsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
N10.31589 (11)0.07187 (9)0.02223 (8)0.0174 (2)
N20.47539 (12)0.25920 (10)0.06321 (8)0.0186 (2)
N30.60853 (12)0.36576 (9)0.00791 (8)0.0200 (2)
N70.21412 (12)0.10660 (10)0.17268 (8)0.0209 (2)
N80.19462 (12)0.08908 (9)0.06531 (8)0.0182 (2)
C1A0.43399 (14)0.18444 (11)0.00738 (9)0.0169 (2)
C40.64962 (14)0.36088 (11)0.09665 (10)0.0182 (2)
C4A0.54365 (13)0.24814 (11)0.11399 (9)0.0167 (2)
C50.53025 (13)0.19280 (11)0.20347 (9)0.0165 (2)
C5A0.40630 (14)0.07551 (11)0.17696 (9)0.0170 (2)
C60.33836 (14)0.01074 (11)0.23877 (10)0.0197 (2)
C8A0.30697 (13)0.02249 (11)0.06549 (9)0.0167 (2)
C210.40119 (14)0.24375 (11)0.17647 (9)0.0186 (2)
C220.23732 (15)0.17973 (12)0.21773 (10)0.0215 (3)
C230.16649 (15)0.16713 (13)0.32885 (11)0.0251 (3)
C240.25785 (16)0.21855 (13)0.39858 (10)0.0260 (3)
C250.42140 (16)0.28241 (13)0.35650 (10)0.0248 (3)
C260.49400 (15)0.29542 (12)0.24581 (10)0.0216 (3)
C410.79153 (14)0.46319 (12)0.17703 (10)0.0216 (3)
C510.63798 (14)0.25437 (12)0.31803 (10)0.0201 (2)
C520.63898 (16)0.38434 (13)0.38477 (10)0.0270 (3)
C530.74051 (19)0.44163 (15)0.49152 (11)0.0394 (4)
C540.84063 (19)0.37008 (19)0.53278 (12)0.0460 (4)
C550.84033 (18)0.24093 (18)0.46707 (13)0.0424 (4)
C560.73975 (15)0.18261 (15)0.36011 (11)0.0290 (3)
C610.38635 (16)0.00210 (13)0.36103 (10)0.0262 (3)
C810.06502 (14)0.17901 (11)0.02190 (10)0.0182 (2)
C820.02632 (14)0.15679 (12)0.12668 (10)0.0216 (3)
C830.10312 (15)0.24664 (12)0.20898 (11)0.0244 (3)
C840.19393 (15)0.35728 (13)0.18804 (11)0.0251 (3)
C850.15356 (15)0.37876 (12)0.08371 (11)0.0250 (3)
C860.02377 (15)0.29142 (12)0.00117 (10)0.0227 (3)
H220.17420.14480.17030.026*
H230.05460.12300.35740.030*
H240.20880.21010.47440.031*
H250.48430.31760.40400.030*
H260.60600.33920.21750.026*
H41A0.85090.51590.13520.032*
H41B0.86450.41720.21140.032*
H41C0.75250.52380.23730.032*
H520.56980.43400.35700.032*
H530.74100.53050.53630.047*
H540.90960.40930.60610.055*
H550.90970.19170.49550.051*
H560.74020.09380.31560.035*
H61A0.30460.06620.38030.039*
H61B0.39310.08990.40980.039*
H61C0.49290.02420.37340.039*
H820.08760.08110.14180.026*
H830.12970.23200.28060.029*
H840.28270.41760.24450.030*
H850.21550.45420.06860.030*
H860.00460.30820.06940.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0184 (5)0.0163 (5)0.0175 (5)0.0028 (4)0.0033 (4)0.0060 (4)
N20.0193 (5)0.0175 (5)0.0163 (5)0.0011 (4)0.0000 (4)0.0061 (4)
N30.0194 (5)0.0169 (5)0.0203 (5)0.0006 (4)0.0012 (4)0.0048 (4)
N70.0265 (5)0.0200 (5)0.0166 (5)0.0035 (4)0.0047 (4)0.0075 (4)
N80.0202 (5)0.0176 (5)0.0154 (5)0.0004 (4)0.0025 (4)0.0057 (4)
C1A0.0179 (5)0.0162 (5)0.0172 (6)0.0048 (4)0.0036 (4)0.0057 (4)
C40.0186 (6)0.0162 (5)0.0191 (6)0.0039 (4)0.0029 (4)0.0048 (4)
C4A0.0168 (5)0.0153 (5)0.0171 (6)0.0039 (4)0.0024 (4)0.0039 (4)
C50.0174 (5)0.0156 (5)0.0167 (6)0.0062 (4)0.0031 (4)0.0037 (4)
C5A0.0192 (5)0.0162 (5)0.0157 (5)0.0051 (4)0.0027 (4)0.0050 (4)
C60.0234 (6)0.0173 (6)0.0184 (6)0.0047 (5)0.0044 (4)0.0054 (4)
C8A0.0171 (5)0.0150 (5)0.0175 (6)0.0033 (4)0.0036 (4)0.0044 (4)
C210.0243 (6)0.0165 (5)0.0148 (5)0.0059 (5)0.0015 (4)0.0050 (4)
C220.0235 (6)0.0209 (6)0.0213 (6)0.0055 (5)0.0033 (5)0.0087 (5)
C230.0243 (6)0.0254 (6)0.0238 (6)0.0054 (5)0.0011 (5)0.0075 (5)
C240.0332 (7)0.0279 (7)0.0179 (6)0.0109 (5)0.0009 (5)0.0079 (5)
C250.0324 (7)0.0249 (6)0.0203 (6)0.0089 (5)0.0080 (5)0.0092 (5)
C260.0230 (6)0.0206 (6)0.0210 (6)0.0041 (5)0.0038 (5)0.0072 (5)
C410.0212 (6)0.0189 (6)0.0214 (6)0.0000 (5)0.0018 (5)0.0052 (5)
C510.0185 (5)0.0228 (6)0.0175 (6)0.0001 (5)0.0019 (4)0.0079 (5)
C520.0321 (7)0.0242 (6)0.0202 (6)0.0005 (5)0.0031 (5)0.0052 (5)
C530.0471 (9)0.0362 (8)0.0197 (7)0.0124 (7)0.0028 (6)0.0009 (6)
C540.0344 (8)0.0681 (12)0.0209 (7)0.0148 (8)0.0070 (6)0.0140 (7)
C550.0252 (7)0.0708 (11)0.0358 (8)0.0054 (7)0.0031 (6)0.0319 (8)
C560.0240 (6)0.0382 (8)0.0288 (7)0.0077 (5)0.0032 (5)0.0175 (6)
C610.0335 (7)0.0251 (6)0.0181 (6)0.0014 (5)0.0037 (5)0.0080 (5)
C810.0168 (5)0.0176 (6)0.0182 (6)0.0034 (4)0.0035 (4)0.0030 (4)
C820.0214 (6)0.0194 (6)0.0229 (6)0.0017 (5)0.0034 (5)0.0073 (5)
C830.0239 (6)0.0246 (6)0.0218 (6)0.0037 (5)0.0001 (5)0.0060 (5)
C840.0191 (6)0.0236 (6)0.0259 (6)0.0001 (5)0.0013 (5)0.0017 (5)
C850.0231 (6)0.0208 (6)0.0277 (7)0.0019 (5)0.0064 (5)0.0060 (5)
C860.0243 (6)0.0208 (6)0.0215 (6)0.0012 (5)0.0057 (5)0.0065 (5)
Geometric parameters (Å, º) top
N1—C1A1.3337 (15)C26—H260.95
N1—C8A1.3365 (14)C41—H41A0.98
N2—C1A1.3710 (14)C41—H41B0.98
N2—N31.3843 (13)C41—H41C0.98
N2—C211.4141 (14)C51—C521.3931 (18)
N3—C41.3161 (15)C51—C561.3932 (17)
N7—C61.3152 (15)C52—C531.3877 (18)
N7—N81.3881 (13)C52—H520.95
N8—C8A1.3734 (14)C53—C541.378 (2)
N8—C811.4198 (14)C53—H530.95
C1A—C4A1.4212 (15)C54—C551.383 (3)
C4—C4A1.4410 (16)C54—H540.95
C4—C411.4905 (15)C55—C561.3869 (19)
C4A—C51.3992 (16)C55—H550.95
C5—C5A1.3988 (16)C56—H560.95
C5—C511.4850 (16)C61—H61A0.98
C5A—C8A1.4234 (15)C61—H61B0.98
C5A—C61.4370 (16)C61—H61C0.98
C6—C611.4906 (16)C81—C821.3924 (16)
C21—C221.3895 (16)C81—C861.3926 (16)
C21—C261.3937 (16)C82—C831.3909 (16)
C22—C231.3893 (17)C82—H820.95
C22—H220.95C83—C841.3860 (18)
C23—C241.3894 (18)C83—H830.95
C23—H230.95C84—C851.3856 (18)
C24—C251.3879 (18)C84—H840.95
C24—H240.95C85—C861.3853 (16)
C25—C261.3877 (17)C85—H850.95
C25—H250.95C86—H860.95
C1A—N1—C8A110.76 (10)C4—C41—H41A109.5
C1A—N2—N3110.76 (9)C4—C41—H41B109.5
C1A—N2—C21129.90 (10)H41A—C41—H41B109.5
N3—N2—C21119.32 (9)C4—C41—H41C109.5
C4—N3—N2107.36 (9)H41A—C41—H41C109.5
C6—N7—N8107.47 (9)H41B—C41—H41C109.5
C8A—N8—N7110.42 (9)C52—C51—C56119.11 (11)
C8A—N8—C81130.92 (10)C52—C51—C5120.63 (11)
N7—N8—C81118.58 (9)C56—C51—C5120.26 (11)
N1—C1A—N2125.31 (10)C53—C52—C51120.38 (13)
N1—C1A—C4A128.02 (10)C53—C52—H52119.8
N2—C1A—C4A106.64 (10)C51—C52—H52119.8
N3—C4—C4A110.74 (10)C54—C53—C52120.25 (14)
N3—C4—C41119.73 (10)C54—C53—H53119.9
C4A—C4—C41129.53 (10)C52—C53—H53119.9
C5—C4A—C1A119.31 (10)C53—C54—C55119.74 (13)
C5—C4A—C4136.18 (10)C53—C54—H54120.1
C1A—C4A—C4104.49 (10)C55—C54—H54120.1
C5A—C5—C4A114.75 (10)C54—C55—C56120.60 (14)
C5A—C5—C51122.54 (10)C54—C55—H55119.7
C4A—C5—C51122.71 (10)C56—C55—H55119.7
C5—C5A—C8A119.52 (10)C55—C56—C51119.92 (14)
C5—C5A—C6135.78 (11)C55—C56—H56120.0
C8A—C5A—C6104.56 (10)C51—C56—H56120.0
N7—C6—C5A110.85 (10)C6—C61—H61A109.5
N7—C6—C61119.64 (10)C6—C61—H61B109.5
C5A—C6—C61129.49 (11)H61A—C61—H61B109.5
N1—C8A—N8125.71 (10)C6—C61—H61C109.5
N1—C8A—C5A127.62 (10)H61A—C61—H61C109.5
N8—C8A—C5A106.65 (10)H61B—C61—H61C109.5
C22—C21—C26120.33 (10)C82—C81—C86120.00 (11)
C22—C21—N2120.54 (10)C82—C81—N8121.28 (10)
C26—C21—N2119.12 (10)C86—C81—N8118.72 (10)
C23—C22—C21119.55 (11)C83—C82—C81119.25 (11)
C23—C22—H22120.2C83—C82—H82120.4
C21—C22—H22120.2C81—C82—H82120.4
C22—C23—C24120.57 (12)C84—C83—C82121.02 (11)
C22—C23—H23119.7C84—C83—H83119.5
C24—C23—H23119.7C82—C83—H83119.5
C25—C24—C23119.42 (11)C85—C84—C83119.18 (11)
C25—C24—H24120.3C85—C84—H84120.4
C23—C24—H24120.3C83—C84—H84120.4
C26—C25—C24120.68 (11)C86—C85—C84120.68 (11)
C26—C25—H25119.7C86—C85—H85119.7
C24—C25—H25119.7C84—C85—H85119.7
C25—C26—C21119.45 (11)C85—C86—C81119.85 (11)
C25—C26—H26120.3C85—C86—H86120.1
C21—C26—H26120.3C81—C86—H86120.1
C1A—N2—N3—C41.15 (13)C5—C5A—C8A—N10.09 (18)
C21—N2—N3—C4177.31 (10)C6—C5A—C8A—N1176.41 (11)
C6—N7—N8—C8A1.55 (13)C5—C5A—C8A—N8178.38 (10)
C6—N7—N8—C81178.71 (10)C6—C5A—C8A—N81.87 (12)
C8A—N1—C1A—N2179.49 (10)C1A—N2—C21—C2225.02 (18)
C8A—N1—C1A—C4A1.64 (16)N3—N2—C21—C22153.10 (11)
N3—N2—C1A—N1176.83 (10)C1A—N2—C21—C26155.93 (11)
C21—N2—C1A—N14.92 (19)N3—N2—C21—C2625.95 (16)
N3—N2—C1A—C4A1.39 (12)C26—C21—C22—C230.19 (18)
C21—N2—C1A—C4A176.86 (11)N2—C21—C22—C23179.23 (11)
N2—N3—C4—C4A0.42 (13)C21—C22—C23—C240.33 (18)
N2—N3—C4—C41179.38 (10)C22—C23—C24—C250.28 (19)
N1—C1A—C4A—C51.63 (18)C23—C24—C25—C260.09 (19)
N2—C1A—C4A—C5179.79 (10)C24—C25—C26—C210.04 (18)
N1—C1A—C4A—C4177.09 (11)C22—C21—C26—C250.01 (18)
N2—C1A—C4A—C41.07 (12)N2—C21—C26—C25179.06 (10)
N3—C4—C4A—C5178.80 (12)C5A—C5—C51—C52117.76 (13)
C41—C4—C4A—C50.0 (2)C4A—C5—C51—C5261.61 (16)
N3—C4—C4A—C1A0.41 (13)C5A—C5—C51—C5662.32 (16)
C41—C4—C4A—C1A178.42 (11)C4A—C5—C51—C56118.31 (13)
C1A—C4A—C5—C5A0.51 (15)C56—C51—C52—C530.25 (19)
C4—C4A—C5—C5A177.70 (12)C5—C51—C52—C53179.68 (12)
C1A—C4A—C5—C51178.91 (10)C51—C52—C53—C540.4 (2)
C4—C4A—C5—C512.9 (2)C52—C53—C54—C550.4 (2)
C4A—C5—C5A—C8A0.22 (15)C53—C54—C55—C560.2 (2)
C51—C5—C5A—C8A179.64 (10)C54—C55—C56—C510.1 (2)
C4A—C5—C5A—C6174.93 (12)C52—C51—C56—C550.09 (19)
C51—C5—C5A—C64.5 (2)C5—C51—C56—C55179.83 (12)
N8—N7—C6—C5A0.29 (13)C8A—N8—C81—C824.62 (19)
N8—N7—C6—C61178.71 (10)N7—N8—C81—C82171.84 (10)
C5—C5A—C6—N7176.63 (12)C8A—N8—C81—C86175.19 (11)
C8A—C5A—C6—N71.00 (13)N7—N8—C81—C868.34 (16)
C5—C5A—C6—C611.6 (2)C86—C81—C82—C831.06 (17)
C8A—C5A—C6—C61177.22 (12)N8—C81—C82—C83179.13 (11)
C1A—N1—C8A—N8177.21 (11)C81—C82—C83—C840.17 (18)
C1A—N1—C8A—C5A0.77 (16)C82—C83—C84—C850.57 (19)
N7—N8—C8A—N1176.17 (10)C83—C84—C85—C860.26 (19)
C81—N8—C8A—N10.52 (19)C84—C85—C86—C811.49 (19)
N7—N8—C8A—C5A2.16 (12)C82—C81—C86—C851.89 (18)
C81—N8—C8A—C5A178.85 (11)N8—C81—C86—C85178.30 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···N10.952.443.0036 (16)118
C82—H82···N10.952.312.9674 (16)126
C85—H85···N3i0.952.543.4888 (17)173
Symmetry code: (i) x1, y1, z.

Experimental details

Crystal data
Chemical formulaC27H21N5
Mr415.49
Crystal system, space groupTriclinic, 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)
V3)1033.96 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.26 × 0.20
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.968, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
21256, 4711, 3815
Rint0.047
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.105, 1.05
No. of reflections4711
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—C521.3931 (18)C52—C531.3877 (18)
N3—C4—C41119.73 (10)C53—C52—C51120.38 (13)
C4A—C4—C41129.53 (10)C54—C53—C52120.25 (14)
C52—C51—C56119.11 (11)C53—C54—C55119.74 (13)
C52—C51—C5120.63 (11)C54—C55—C56120.60 (14)
C56—C51—C5120.26 (11)C55—C56—C51119.92 (14)
C1A—N2—C21—C2225.02 (18)C5A—C5—C51—C5662.32 (16)
N3—N2—C21—C22153.10 (11)C4A—C5—C51—C56118.31 (13)
C1A—N2—C21—C26155.93 (11)C8A—N8—C81—C824.62 (19)
N3—N2—C21—C2625.95 (16)N7—N8—C81—C82171.84 (10)
C5A—C5—C51—C52117.76 (13)C8A—N8—C81—C86175.19 (11)
C4A—C5—C51—C5261.61 (16)N7—N8—C81—C868.34 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···N10.952.443.0036 (16)118
C82—H82···N10.952.312.9674 (16)126
C85—H85···N3i0.952.543.4888 (17)173
Symmetry code: (i) x1, y1, z.
 

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