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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].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018208/om6158sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018208/om6158Isup2.hkl
Contains datablock I

CCDC reference: 222872

Key indicators

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

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.
[Figure 2] 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
C26H20N6F(000) = 436
Mr = 416.48Dx = 1.353 Mg m3
Triclinic, P1Melting point: 517 K
a = 8.4576 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.6599 (3) ÅCell parameters from 4637 reflections
c = 12.3642 (4) Åθ = 3.1–27.5°
α = 106.9170 (14)°µ = 0.08 mm1
β = 98.6240 (16)°T = 120 K
γ = 100.803 (2)°Block, brown
V = 1022.48 (5) Å30.28 × 0.22 × 0.18 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
4637 independent reflections
Radiation source: fine-focus sealed X-ray tube3732 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ϕ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1010
Tmin = 0.977, Tmax = 0.985k = 1313
19117 measured reflectionsl = 1615
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) = 0.110H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.1734P]
where P = (Fo2 + 2Fc2)/3
4637 reflections(Δ/σ)max < 0.001
291 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C26H20N6γ = 100.803 (2)°
Mr = 416.48V = 1022.48 (5) Å3
Triclinic, P1Z = 2
a = 8.4576 (2) ÅMo Kα radiation
b = 10.6599 (3) ŵ = 0.08 mm1
c = 12.3642 (4) ÅT = 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)
Tmin = 0.977, Tmax = 0.985Rint = 0.050
19117 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.03Δρmax = 0.25 e Å3
4637 reflectionsΔρmin = 0.25 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
N10.31352 (11)0.06622 (9)0.02226 (8)0.0183 (2)
N20.46861 (12)0.25463 (10)0.06259 (8)0.0197 (2)
N30.60148 (12)0.36471 (10)0.00499 (8)0.0214 (2)
N70.22367 (12)0.10898 (10)0.17481 (8)0.0219 (2)
N80.19836 (12)0.09346 (10)0.06625 (8)0.0194 (2)
N520.60600 (13)0.38270 (11)0.38405 (9)0.0257 (2)
C1A0.43165 (14)0.18011 (11)0.00781 (10)0.0178 (2)
C40.64613 (14)0.36174 (11)0.10053 (10)0.0195 (2)
C4A0.54369 (13)0.24750 (11)0.11638 (10)0.0179 (2)
C50.53309 (13)0.19511 (11)0.20688 (10)0.0177 (2)
C5A0.41189 (14)0.07542 (11)0.17944 (9)0.0181 (2)
C60.34921 (14)0.01033 (12)0.24163 (10)0.0207 (3)
C8A0.30884 (13)0.01859 (11)0.06626 (10)0.0174 (2)
C210.39228 (14)0.23594 (11)0.17791 (10)0.0196 (2)
C220.22943 (15)0.16217 (12)0.22427 (10)0.0229 (3)
C230.15769 (15)0.14562 (13)0.33791 (11)0.0257 (3)
C240.24560 (16)0.20351 (13)0.40458 (11)0.0267 (3)
C250.40694 (16)0.27891 (13)0.35671 (11)0.0266 (3)
C260.48110 (15)0.29504 (12)0.24422 (10)0.0240 (3)
C410.78873 (15)0.46651 (12)0.18448 (10)0.0233 (3)
C510.63797 (14)0.26626 (12)0.32535 (10)0.0193 (2)
C530.69853 (16)0.44902 (13)0.49086 (11)0.0296 (3)
C540.82234 (16)0.40458 (15)0.54260 (12)0.0342 (3)
C550.85259 (17)0.28416 (17)0.48169 (12)0.0390 (4)
C560.75932 (16)0.21315 (14)0.37111 (11)0.0307 (3)
C610.40634 (16)0.00020 (13)0.36462 (10)0.0264 (3)
C810.06302 (14)0.18390 (11)0.02100 (10)0.0186 (2)
C820.01656 (15)0.16302 (12)0.12590 (10)0.0223 (3)
C830.12059 (15)0.25137 (12)0.20700 (11)0.0242 (3)
C840.21210 (15)0.35990 (12)0.18481 (11)0.0245 (3)
C850.16322 (15)0.38136 (13)0.08105 (11)0.0258 (3)
C860.02569 (15)0.29492 (12)0.00072 (10)0.0235 (3)
H220.16790.12350.17860.028*
H230.04720.09410.37020.031*
H240.19600.19170.48220.032*
H250.46710.31990.40170.032*
H260.59190.34610.21240.029*
H41A0.83570.52980.14730.035*
H41B0.87290.42280.20930.035*
H41C0.75130.51580.25200.035*
H530.67730.53170.53340.036*
H540.88540.45560.61840.041*
H550.93660.25020.51530.047*
H560.77800.12990.32750.037*
H61A0.32880.06590.38420.040*
H61B0.41190.09150.41520.040*
H61C0.51600.01800.37530.040*
H820.07810.08890.14200.027*
H830.15220.23730.27870.029*
H840.30710.41870.24010.029*
H850.22450.45610.06560.031*
H860.00790.31130.07120.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0201 (5)0.0176 (5)0.0168 (5)0.0040 (4)0.0040 (4)0.0057 (4)
N20.0206 (5)0.0181 (5)0.0173 (5)0.0002 (4)0.0010 (4)0.0056 (4)
N30.0212 (5)0.0182 (5)0.0210 (5)0.0004 (4)0.0021 (4)0.0047 (4)
N70.0267 (5)0.0229 (5)0.0165 (5)0.0049 (4)0.0043 (4)0.0077 (4)
N80.0217 (5)0.0190 (5)0.0159 (5)0.0017 (4)0.0020 (4)0.0067 (4)
N520.0292 (6)0.0236 (5)0.0196 (5)0.0067 (4)0.0001 (4)0.0026 (4)
C1A0.0179 (5)0.0172 (5)0.0182 (6)0.0047 (4)0.0038 (4)0.0055 (4)
C40.0192 (6)0.0178 (6)0.0203 (6)0.0043 (5)0.0038 (4)0.0048 (4)
C4A0.0176 (5)0.0172 (5)0.0168 (6)0.0041 (4)0.0025 (4)0.0033 (4)
C50.0173 (5)0.0177 (5)0.0178 (6)0.0067 (4)0.0034 (4)0.0043 (4)
C5A0.0197 (5)0.0181 (6)0.0158 (5)0.0059 (4)0.0027 (4)0.0044 (4)
C60.0232 (6)0.0198 (6)0.0184 (6)0.0058 (5)0.0039 (5)0.0052 (5)
C8A0.0178 (5)0.0167 (5)0.0174 (5)0.0048 (4)0.0040 (4)0.0045 (4)
C210.0246 (6)0.0183 (6)0.0157 (6)0.0070 (5)0.0019 (4)0.0054 (4)
C220.0239 (6)0.0240 (6)0.0222 (6)0.0057 (5)0.0042 (5)0.0099 (5)
C230.0228 (6)0.0275 (6)0.0243 (6)0.0061 (5)0.0006 (5)0.0077 (5)
C240.0314 (7)0.0317 (7)0.0187 (6)0.0128 (5)0.0033 (5)0.0087 (5)
C250.0324 (7)0.0297 (7)0.0227 (6)0.0100 (5)0.0090 (5)0.0128 (5)
C260.0258 (6)0.0237 (6)0.0228 (6)0.0048 (5)0.0048 (5)0.0092 (5)
C410.0226 (6)0.0199 (6)0.0228 (6)0.0008 (5)0.0024 (5)0.0041 (5)
C510.0182 (5)0.0207 (6)0.0172 (6)0.0025 (4)0.0020 (4)0.0059 (4)
C530.0333 (7)0.0270 (7)0.0208 (6)0.0039 (5)0.0015 (5)0.0007 (5)
C540.0256 (7)0.0449 (8)0.0215 (7)0.0023 (6)0.0022 (5)0.0027 (6)
C550.0286 (7)0.0576 (10)0.0291 (7)0.0187 (7)0.0036 (6)0.0115 (7)
C560.0293 (7)0.0355 (7)0.0261 (7)0.0149 (6)0.0015 (5)0.0058 (6)
C610.0325 (7)0.0274 (7)0.0177 (6)0.0037 (5)0.0034 (5)0.0081 (5)
C810.0178 (5)0.0181 (5)0.0172 (6)0.0040 (4)0.0034 (4)0.0024 (4)
C820.0243 (6)0.0199 (6)0.0210 (6)0.0027 (5)0.0033 (5)0.0065 (5)
C830.0253 (6)0.0246 (6)0.0205 (6)0.0057 (5)0.0012 (5)0.0064 (5)
C840.0201 (6)0.0235 (6)0.0238 (6)0.0023 (5)0.0028 (5)0.0015 (5)
C850.0250 (6)0.0222 (6)0.0263 (6)0.0006 (5)0.0068 (5)0.0056 (5)
C860.0255 (6)0.0236 (6)0.0202 (6)0.0026 (5)0.0052 (5)0.0076 (5)
Geometric parameters (Å, º) top
N1—C1A1.3347 (15)C25—C261.3842 (17)
N1—C8A1.3364 (15)C25—H250.95
N2—C1A1.3702 (15)C26—H260.95
N2—N31.3879 (13)C41—H41A0.98
N2—C211.4142 (14)C41—H41B0.98
N3—C41.3139 (15)C41—H41C0.98
N7—C61.3147 (15)C51—C561.3871 (17)
N7—N81.3896 (13)C53—C541.3753 (19)
N8—C8A1.3717 (15)C53—H530.95
N8—C811.4192 (14)C54—C551.378 (2)
N52—C531.3400 (16)C54—H540.95
N52—C511.3420 (15)C55—C561.3838 (19)
C1A—C4A1.4206 (15)C55—H550.95
C4—C4A1.4375 (16)C56—H560.95
C4—C411.4914 (16)C61—H61A0.98
C4A—C51.3953 (17)C61—H61B0.98
C5—C5A1.3954 (16)C61—H61C0.98
C5—C511.4898 (15)C81—C821.3908 (16)
C5A—C8A1.4240 (15)C81—C861.3957 (17)
C5A—C61.4345 (17)C82—C831.3893 (16)
C6—C611.4894 (16)C82—H820.95
C21—C221.3924 (17)C83—C841.3877 (18)
C21—C261.3933 (17)C83—H830.95
C22—C231.3905 (17)C84—C851.3844 (18)
C22—H220.95C84—H840.95
C23—C241.3860 (19)C85—C861.3883 (17)
C23—H230.95C85—H850.95
C24—C251.3886 (18)C86—H860.95
C24—H240.95
C1A—N1—C8A110.97 (9)C25—C26—H26120.2
C1A—N2—N3110.74 (9)C21—C26—H26120.2
C1A—N2—C21130.19 (10)C4—C41—H41A109.5
N3—N2—C21119.06 (9)C4—C41—H41B109.5
C4—N3—N2107.25 (9)H41A—C41—H41B109.5
C6—N7—N8107.25 (10)C4—C41—H41C109.5
C8A—N8—N7110.61 (9)H41A—C41—H41C109.5
C8A—N8—C81130.72 (10)H41B—C41—H41C109.5
N7—N8—C81118.49 (9)N52—C51—C56122.88 (11)
C53—N52—C51117.14 (10)N52—C51—C5115.80 (10)
N1—C1A—N2125.73 (10)C56—C51—C5121.31 (10)
N1—C1A—C4A127.79 (10)N52—C53—C54123.90 (12)
N2—C1A—C4A106.48 (10)N52—C53—H53118.0
N3—C4—C4A110.79 (10)C54—C53—H53118.0
N3—C4—C41120.45 (11)C53—C54—C55118.28 (12)
C4A—C4—C41128.74 (11)C53—C54—H54120.9
C5—C4A—C1A119.31 (10)C55—C54—H54120.9
C5—C4A—C4135.98 (11)C54—C55—C56119.28 (12)
C1A—C4A—C4104.71 (10)C54—C55—H55120.4
C5A—C5—C4A115.03 (10)C56—C55—H55120.4
C5A—C5—C51122.83 (10)C55—C56—C51118.50 (12)
C4A—C5—C51122.07 (10)C55—C56—H56120.7
C5—C5A—C8A119.47 (10)C51—C56—H56120.7
C5—C5A—C6135.71 (11)C6—C61—H61A109.5
C8A—C5A—C6104.67 (10)C6—C61—H61B109.5
N7—C6—C5A110.96 (10)H61A—C61—H61B109.5
N7—C6—C61119.88 (11)C6—C61—H61C109.5
C5A—C6—C61129.15 (11)H61A—C61—H61C109.5
N1—C8A—N8126.07 (10)H61B—C61—H61C109.5
N1—C8A—C5A127.41 (10)C82—C81—C86119.88 (11)
N8—C8A—C5A106.49 (10)C82—C81—N8121.49 (10)
C22—C21—C26120.14 (11)C86—C81—N8118.63 (10)
C22—C21—N2120.76 (11)C83—C82—C81119.47 (11)
C26—C21—N2119.09 (10)C83—C82—H82120.3
C23—C22—C21119.43 (11)C81—C82—H82120.3
C23—C22—H22120.3C82—C83—C84121.01 (12)
C21—C22—H22120.3C82—C83—H83119.5
C24—C23—C22120.73 (12)C84—C83—H83119.5
C24—C23—H23119.6C85—C84—C83119.13 (11)
C22—C23—H23119.6C85—C84—H84120.4
C23—C24—C25119.30 (11)C83—C84—H84120.4
C23—C24—H24120.3C84—C85—C86120.74 (12)
C25—C24—H24120.3C84—C85—H85119.6
C26—C25—C24120.78 (12)C86—C85—H85119.6
C26—C25—H25119.6C85—C86—C81119.74 (11)
C24—C25—H25119.6C85—C86—H86120.1
C25—C26—C21119.60 (11)C81—C86—H86120.1
C1A—N2—N3—C41.15 (12)C5—C5A—C8A—N10.62 (17)
C21—N2—N3—C4178.00 (9)C6—C5A—C8A—N1176.81 (11)
C6—N7—N8—C8A1.05 (12)C5—C5A—C8A—N8177.32 (10)
C6—N7—N8—C81176.71 (9)C6—C5A—C8A—N81.13 (11)
C8A—N1—C1A—N2179.82 (10)C1A—N2—C21—C2222.81 (18)
C8A—N1—C1A—C4A0.72 (16)N3—N2—C21—C22156.16 (10)
N3—N2—C1A—N1178.15 (10)C1A—N2—C21—C26158.64 (12)
C21—N2—C1A—N12.82 (19)N3—N2—C21—C2622.40 (15)
N3—N2—C1A—C4A1.40 (12)C26—C21—C22—C231.40 (17)
C21—N2—C1A—C4A177.63 (10)N2—C21—C22—C23179.95 (10)
N2—N3—C4—C4A0.41 (12)C21—C22—C23—C241.06 (18)
N2—N3—C4—C41179.07 (10)C22—C23—C24—C250.10 (18)
N1—C1A—C4A—C51.56 (17)C23—C24—C25—C260.93 (19)
N2—C1A—C4A—C5178.90 (10)C24—C25—C26—C210.58 (18)
N1—C1A—C4A—C4178.45 (11)C22—C21—C26—C250.59 (17)
N2—C1A—C4A—C41.09 (11)N2—C21—C26—C25179.16 (10)
N3—C4—C4A—C5179.56 (12)C53—N52—C51—C560.71 (19)
C41—C4—C4A—C51.9 (2)C53—N52—C51—C5179.94 (11)
N3—C4—C4A—C1A0.43 (12)C5A—C5—C51—N52108.40 (13)
C41—C4—C4A—C1A178.10 (11)C4A—C5—C51—N5268.30 (14)
C1A—C4A—C5—C5A1.72 (15)C5A—C5—C51—C5670.95 (16)
C4—C4A—C5—C5A178.30 (12)C4A—C5—C51—C56112.34 (14)
C1A—C4A—C5—C51175.22 (10)C51—N52—C53—C540.1 (2)
C4—C4A—C5—C514.8 (2)N52—C53—C54—C550.6 (2)
C4A—C5—C5A—C8A1.32 (15)C53—C54—C55—C560.6 (2)
C51—C5—C5A—C8A175.60 (10)C54—C55—C56—C510.0 (2)
C4A—C5—C5A—C6176.03 (12)N52—C51—C56—C550.7 (2)
C51—C5—C5A—C60.9 (2)C5—C51—C56—C55180.00 (12)
N8—N7—C6—C5A0.28 (13)C8A—N8—C81—C823.78 (18)
N8—N7—C6—C61179.97 (10)N7—N8—C81—C82170.86 (10)
C5—C5A—C6—N7175.78 (12)C8A—N8—C81—C86177.07 (11)
C8A—C5A—C6—N70.53 (12)N7—N8—C81—C868.29 (15)
C5—C5A—C6—C613.9 (2)C86—C81—C82—C831.59 (17)
C8A—C5A—C6—C61179.12 (11)N8—C81—C82—C83177.55 (10)
C1A—N1—C8A—N8177.31 (10)C81—C82—C83—C840.15 (18)
C1A—N1—C8A—C5A0.24 (15)C82—C83—C84—C851.31 (18)
N7—N8—C8A—N1176.60 (10)C83—C84—C85—C860.74 (18)
C81—N8—C8A—N11.64 (18)C84—C85—C86—C810.98 (18)
N7—N8—C8A—C5A1.37 (12)C82—C81—C86—C852.15 (17)
C81—N8—C8A—C5A176.34 (11)N8—C81—C86—C85177.02 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···N10.952.433.0029 (16)119
C82—H82···N10.952.312.9721 (16)126
C85—H85···N3i0.952.553.4922 (18)173
Symmetry code: (i) x1, y1, z.

Experimental details

Crystal data
Chemical formulaC26H20N6
Mr416.48
Crystal system, space groupTriclinic, 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)
V3)1022.48 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.28 × 0.22 × 0.18
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.977, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
19117, 4637, 3732
Rint0.050
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.110, 1.03
No. of reflections4637
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—C1A1.3347 (15)N52—C531.3400 (16)
N1—C8A1.3364 (15)N52—C511.3420 (15)
N2—N31.3879 (13)C1A—C4A1.4206 (15)
N3—C41.3139 (15)C4—C4A1.4375 (16)
N7—C61.3147 (15)C4A—C51.3953 (17)
N7—N81.3896 (13)C5—C5A1.3954 (16)
N8—C8A1.3717 (15)C5A—C8A1.4240 (15)
C1A—N1—C8A110.97 (9)C5A—C5—C4A115.03 (10)
C1A—N2—N3110.74 (9)C5A—C5—C51122.83 (10)
C1A—N2—C21130.19 (10)C4A—C5—C51122.07 (10)
N3—N2—C21119.06 (9)C5—C5A—C8A119.47 (10)
C4—N3—N2107.25 (9)C5—C5A—C6135.71 (11)
C6—N7—N8107.25 (10)C8A—C5A—C6104.67 (10)
C8A—N8—N7110.61 (9)N7—C6—C5A110.96 (10)
C8A—N8—C81130.72 (10)N7—C6—C61119.88 (11)
N7—N8—C81118.49 (9)C5A—C6—C61129.15 (11)
C53—N52—C51117.14 (10)N1—C8A—N8126.07 (10)
N1—C1A—N2125.73 (10)N1—C8A—C5A127.41 (10)
N1—C1A—C4A127.79 (10)N8—C8A—C5A106.49 (10)
N2—C1A—C4A106.48 (10)N52—C51—C56122.88 (11)
N3—C4—C4A110.79 (10)N52—C51—C5115.80 (10)
N3—C4—C41120.45 (11)N52—C53—C54123.90 (12)
C4A—C4—C41128.74 (11)C53—C54—C55118.28 (12)
C5—C4A—C1A119.31 (10)C54—C55—C56119.28 (12)
C5—C4A—C4135.98 (11)C55—C56—C51118.50 (12)
C1A—C4A—C4104.71 (10)
C1A—N2—C21—C2222.81 (18)C5A—C5—C51—C5670.95 (16)
N3—N2—C21—C22156.16 (10)C4A—C5—C51—C56112.34 (14)
C1A—N2—C21—C26158.64 (12)C8A—N8—C81—C823.78 (18)
N3—N2—C21—C2622.40 (15)N7—N8—C81—C82170.86 (10)
C5A—C5—C51—N52108.40 (13)C8A—N8—C81—C86177.07 (11)
C4A—C5—C51—N5268.30 (14)N7—N8—C81—C868.29 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···N10.952.433.0029 (16)119
C82—H82···N10.952.312.9721 (16)126
C85—H85···N3i0.952.553.4922 (18)173
Symmetry code: (i) x1, y1, z.
 

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