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Both 6-(1H-indol-3-yl)-3-methyl-4-(4-methyl­phen­yl)-1-phen­yl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and 6-(1H-indol-3-yl)-3-methyl-4-(4-methoxy­phen­yl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile crystallize from dimethyl­formamide solutions as stoichiometric 1:1 solvates, viz. C29H21N5·C3H7NO, (I), and C29H21N5O·C3H7NO, (II), respectively; however, 6-(1H-indol-3-yl)-3-methyl-1-phenyl-4-(3,4,5-trimethoxy­phen­yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile, C31H25N5O3, (III), crystallizes in the unsolvated form. The heterocyclic components of (I) are linked by C—H...π(arene) hydrogen bonds to form cyclic centrosymmetric dimers, from which the solvent mol­ecules are pendent, linked by N—H...O hydrogen bonds. In (II), the heterocyclic components are linked by a combination of C—H...N and C—H...π(arene) hydrogen bonds into chains containing two types of centrosymmetric ring, and the pendent solvent mol­ecules are linked to these chains by N—H...O hydrogen bonds. Mol­ecules of (III) are linked into simple C(12) chains by an N—H...O hydrogen bond, and these chains are weakly linked into pairs by an aromatic π–π stacking inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107013649/fa3082sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107013649/fa3082Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107013649/fa3082IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107013649/fa3082IIIsup4.hkl
Contains datablock III

CCDC references: 649085; 649086; 649087

Comment top

We report here the structures of three 6-(1H-indol-3-yl)-3-methyl-1-phenyl-4-aryl-1H- pyrazolo[3,4-b]pyridine-5-carbonitriles, two of which crystallize from dimethylformamide solutions as stoichiometric monosolvates, namely 6-(1H-indol-3-yl)-3-methyl-1-phenyl-4-(4-methylphenyl)-1H- pyrazolo[3,4-b]pyridine-5-carbonitrile–dimethylformamide (1/1), (I), 6-(1H-indol-3-yl)-3-methyl-1-phenyl-4-(4-methoxyphenyl)-1H- pyrazolo[3,4-b]pyridine-5-carbonitrile–dimethylformamide (1/1), (II), and the solvent-free 6-(1H-indol-3-yl)-3-methyl-1-phenyl- 4-(3,4,5-trimethoxyphenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile, (III) (Figs. 1–3). The heterocyclic components within this group differ only in the substituents on the pendent aryl ring (C41–C46).

As a part of our exploration of routes to new biologically interesting pyrazolo[3,4-b]pyridine derivatives, we have sought methods for the introduction of an indolyl residue as a substituent at C-6, in order to establish the influence of this naturally occurring group on the biological activity of the resulting products. To this end, we have adapted the multicomponent reaction between substituted aryl aldehydes, an aminopyrazole and a ketone derivative, which has been used for the synthesis of fused heterocyclic systems (Quiroga et al., 2007) to include the use of 3-(2-cyanoacetyl)indole. The corresponding reactions utilizing mixtures of 5-amino-3-methyl-1-phenylpyrazole and 3-(2-cyanoacetyl)indole with three different substituted aryl aldehydes were conducted using microwave irradiation under solvent-free conditions to produce the corresponding 6-(1H-indol-3-yl)-3-methyl-1-phenyl-4-arylpyrazolo[3,4-b]pyridine- 5-carbonitriles, (I)–(III) (Scheme 2).

With the exception of the methoxy groups in compounds (II) and (III), the skeletal conformations of the heterocyclic components can be defined in terms of just three torsion angles, which define the orientation of the three cyclic substituents relative to the central pyrazolopyridine unit (Table 1). In each compound, the rotation of the substituents out of the plane of the pyrazolopyridine unit is least for the C11–C16 aryl ring and most for the C41–C46 aryl ring. Simple steric considerations, particularly those involving the methyl and cyano substituents at atoms C3 and C5, account for this order, although not for the detailed differences in the torsion angles.

The methoxy C atom in compound (II) is almost coplanar with the adjacent aryl ring, as are the methoxy atoms C431 and C451 in compound (III); on the other hand, the C44/O44/C441 plane defining the orientation of the central methoxy substituent in compound (III) is at an angle of almost 60° to the adjacent aryl ring. The exocyclic C—C—O bond angles exhibit the usual pattern, with the two values at each substituent differing by almost 10° for the in-plane methoxy groups, while for the out of plane methoxy group in compound (III), these angles differ by very much less (Table 1).

In each of the solvates (I) and (II), the molecular components within the selected asymmetric units are linked by an N—H···O hydrogen bond (Table 2), so that the N—H bond is not available for the formation of a hydrogen bond to another heterocyclic molecule. In compound (I), the heterocyclic components are linked by a C—H···π(arene) hydrogen bond; atom C42 at (x, y, z) acts as a hydrogen-bond donor to the aryl ring C63A/C64–C67/C67A at (1 - x, 1 - y, 1 - z), so generating by inversion a cyclic centrosymmetric dimer, centred at (1/2, 1/2, 1/2) (Fig. 4), from which two dimethylformamide molecules are pendent.

The aggregation of the pyrazolopyridine components in compound (II) utilizes both C—H···π(arene) and C—H···N hydrogen bonds (Table 2). As in compound (I), atom C42 at (x, y, z) acts as a hydrogen-bond donor to the aryl ring C63A/C64–C67/C67A, now at (1/2 - x, 3/2 - y, 1 - z), so generating by inversion a cyclic centrosymmetric motif. In addition, C46 at (x, y, z) acts as a donor to nitrile atom N51 at (1/2 - x, 1/2 - y, 1 - z), thus generating by inversion a centrosymmetric R22(14) (Bernstein et al., 1995) motif. Propagation by inversion of these two hydrogen bonds then generates a chain of rings parallel to [010], with rings containing pairs of C—H···π(arene) hydrogen bonds centred at (1/4, n - 1/4, 1/2) (where n represents zero or an integer) alternating with rings containing pairs of C—H···N hydrogen bonds centred at (1/4, n + 1/4, 1/2) (where n represents zero or an integer) (Fig. 5). The dimethylformamide solvent molecules are pendent from the chain, linked to it via N—H···O hydrogen bonds. Four chains of this type pass through each unit cell, but there are no direction-specific interactions between the chains.

In the solvent-free compound (III), the molecules are linked by a single, nearly-linear N—H···O hydrogen bond, but C—H···N and C—H···π(arene) hydrogen bonds are absent. Atom N63 in the molecule at (x, y, z) acts as a hydrogen-bond donor to the central methoxy atom O44 in the molecule at (x, -1 + y, z), so generating by translation a C(12) chain running parallel to the [010] direction (Fig. 6).

In each compound, there is a rather weak ππ stacking interaction involving the pyridyl rings in pairs of molecules related by inversion. In compounds (I) and (III), the rings involved are at (x, y, z) and (1 - x, 1 - y, 1 - z), while in compound (II), they are at (x, y, z) and (1/2 - x, 3/2 - y, 1 - z). The interplanar spacings in compounds (I), (II) and (III) are 3.632 (2), 3.538 (2) and 3.583 (2) Å, respectively, and the ring-centroid separations are 3.956 (2), 3.815 (2) and 3.831 (2) Å, corresponding to ring-centroid offsets of 1.568 (2), 1.427 (2) and 1.356 (2) Å, respectively. In compounds (I) and (II), the interactions weakly augment the actions of the C—H···π(arene) hydrogen bonds; in compound (III), the stacking interactions link, albeit weakly, an antiparallel pair of C(12) chains.

Related literature top

For related literature, see: Bernstein et al. (1995); Quiroga et al. (2007).

Experimental top

Equimolar mixtures (0.5 mmol of each component) of 5-amino-3-methyl-1-phenylpyrazole, 3-(2-cyanoacetyl)indole and the appropriate aldehyde [4-methylbenzaldehyde for (I), 4-methoxybenzaldehyde for (II) and 3,4,5-trimethoxybenzaldehyde for (III)] were subjected to microwave irradiation in the absence of solvent (maximum power 300 W during 9 min at a controlled temperature of 473 K) using a focused microwave reactor (CEM Discover). The resulting reaction mixtures were then extracted with hot ethanol/dimethylformamide mixtures (2:1 v/v): the solid products were collected by filtration and washed successively with ethanol and diethyl ether to yield crystals of compounds (I)–(III) suitable for single-crystal X-ray diffraction. Compound (I), yield 89%, m.p. 547 K; MS (70 eV) m/z (%) = 439(100, M+), 424 (37), 397 (6), 77 (40), 51 (30). Compound (II), yield 85%, m.p. 543 K; MS (70 eV) m/z (%) = 455 (100, M+), 424 (9), 409 (6), 77 (8). Compound (III), yield 88%, m.p. 548; MS (70 eV) m/z (%) = 515 (100, M+), 484 (23), 414 (8), 258 (10), 77 (31), 51 (13).

Refinement top

Crystals of compounds (I) and (III) are triclinic; for each compound space group P1 was selected, and confirmed by the structure analysis. For compound (II), the systematic absences permitted C2/c and Cc as possible space groups; C2/c was selected, and confirmed by the structure analysis. All H atoms were located in difference maps, and then treated as riding atoms with C—H distances of 0.95 Å (aromatic and formyl) or 0.98 Å (methyl) and N—H of 0.88 Å, and with Uiso(H) = kUeq(carrier), where k = 1.5 for the methyl groups and k = 1.2 for all other H atoms.

Computing details top

For all compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The independent components of compound (I), showing the atom-labelling scheme and the N—H···O hydrogen bond within the selected asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The independent components of compound (II), showing the atom-labelling scheme and the N—H···O hydrogen bond within the selected asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 3] Fig. 3. A molecule of compound (III) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 4] Fig. 4. Part of the crystal structure of compound (I), showing the formation of a centrosymmetric hydrogen-bonded dimer. For the sake of clarity, the solvent molecule and the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 - x, 1 - y, 1 - z).
[Figure 5] Fig. 5. A stereoview of part of the crystal structure of compound (II), showing the formation of a hydrogen-bonded chain along [010], containing two types of centrosymmetric ring. For the sake of clarity, the solvent molecule and the H atoms not involved in the motif shown have been omitted.
[Figure 6] Fig. 6. Part of the crystal structure of compound (III), showing the formation of a hydrogen-bonded C(12) chain along [010]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, -1 + y, z) and (x, 1 + y, z), respectively.
(I) 6-(1H-indol-3-yl)-3-methyl-4-(4-methylphenyl)-1-phenyl-1H- pyrazolo[3,4-b]pyridine-5-carbonitrile top
Crystal data top
C29H21N5·C3H7NOZ = 2
Mr = 512.60F(000) = 540
Triclinic, P1Dx = 1.297 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8060 (3) ÅCell parameters from 5996 reflections
b = 10.1820 (3) Åθ = 3.0–27.5°
c = 13.818 (2) ŵ = 0.08 mm1
α = 97.035 (6)°T = 120 K
β = 104.455 (6)°Block, colourless
γ = 96.171 (3)°0.40 × 0.18 × 0.18 mm
V = 1312.2 (2) Å3
Data collection top
Bruker–Nonius KappaCCD
diffractometer
5996 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode3816 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
ϕ & ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1313
Tmin = 0.961, Tmax = 0.985l = 1717
31081 measured reflections
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0617P)2 + 0.7281P]
where P = (Fo2 + 2Fc2)/3
5996 reflections(Δ/σ)max < 0.001
356 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C29H21N5·C3H7NOγ = 96.171 (3)°
Mr = 512.60V = 1312.2 (2) Å3
Triclinic, P1Z = 2
a = 9.8060 (3) ÅMo Kα radiation
b = 10.1820 (3) ŵ = 0.08 mm1
c = 13.818 (2) ÅT = 120 K
α = 97.035 (6)°0.40 × 0.18 × 0.18 mm
β = 104.455 (6)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
5996 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
3816 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.985Rint = 0.048
31081 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.06Δρmax = 0.37 e Å3
5996 reflectionsΔρmin = 0.31 e Å3
356 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.17256 (17)0.43480 (15)0.53720 (12)0.0223 (4)
C110.0798 (2)0.32981 (19)0.46645 (15)0.0231 (4)
C120.0323 (2)0.2628 (2)0.49438 (16)0.0269 (5)
C130.1234 (2)0.1595 (2)0.42691 (17)0.0327 (5)
C140.1064 (2)0.1244 (2)0.33136 (17)0.0324 (5)
C150.0056 (2)0.1910 (2)0.30436 (17)0.0320 (5)
C160.1003 (2)0.2927 (2)0.37157 (15)0.0275 (5)
N20.16228 (18)0.45428 (16)0.63587 (12)0.0255 (4)
C30.2590 (2)0.55566 (19)0.68598 (15)0.0238 (4)
C310.2692 (2)0.6014 (2)0.79472 (15)0.0309 (5)
C3A0.3375 (2)0.60717 (19)0.62060 (14)0.0218 (4)
C40.4431 (2)0.71493 (18)0.62641 (14)0.0215 (4)
C410.5144 (2)0.80261 (19)0.72421 (14)0.0218 (4)
C420.5853 (2)0.7467 (2)0.80643 (15)0.0279 (5)
C430.6468 (2)0.8245 (2)0.89987 (15)0.0287 (5)
C440.6389 (2)0.9605 (2)0.91438 (15)0.0256 (4)
C4410.7015 (2)1.0440 (2)1.01756 (16)0.0350 (5)
C450.5709 (2)1.0160 (2)0.83178 (15)0.0268 (5)
C460.5096 (2)0.93929 (19)0.73794 (15)0.0248 (4)
C50.47434 (19)0.73448 (18)0.53544 (14)0.0213 (4)
C510.5754 (2)0.8462 (2)0.53358 (15)0.0256 (4)
N510.65463 (19)0.93516 (18)0.52840 (14)0.0342 (4)
C60.40680 (19)0.64614 (18)0.44291 (14)0.0206 (4)
C610.4389 (2)0.65856 (18)0.34648 (14)0.0210 (4)
C620.5649 (2)0.71023 (19)0.32929 (15)0.0238 (4)
N630.55728 (17)0.68867 (16)0.22899 (12)0.0252 (4)
C63A0.4247 (2)0.62111 (18)0.17701 (14)0.0224 (4)
C640.3699 (2)0.5764 (2)0.07383 (15)0.0280 (5)
C650.2335 (2)0.5086 (2)0.04160 (16)0.0313 (5)
C660.1523 (2)0.4892 (2)0.11050 (15)0.0289 (5)
C670.2061 (2)0.53492 (19)0.21261 (15)0.0247 (4)
C67A0.3468 (2)0.60076 (18)0.24838 (14)0.0213 (4)
N70.30754 (16)0.54313 (15)0.43858 (12)0.0215 (4)
C7A0.2762 (2)0.52825 (18)0.52556 (14)0.0216 (4)
N201.02010 (18)0.83307 (17)0.20145 (13)0.0286 (4)
C200.8953 (2)0.7928 (2)0.21673 (16)0.0273 (5)
O200.78473 (15)0.74965 (15)0.14953 (11)0.0329 (4)
C211.1434 (2)0.8874 (2)0.28574 (18)0.0365 (5)
C221.0394 (2)0.8270 (2)0.10081 (17)0.0382 (6)
H120.04620.28780.55940.032*
H130.19840.11220.44660.039*
H140.17100.05530.28460.039*
H150.01790.16670.23880.038*
H160.17830.33650.35290.033*
H31A0.18420.56120.81140.046*
H31B0.27600.69910.80690.046*
H31C0.35390.57400.83720.046*
H420.59140.65370.79810.033*
H430.69490.78430.95470.034*
H44A0.70021.13891.01180.053*
H44B0.79981.02841.04420.053*
H44C0.64501.01891.06350.053*
H450.56631.10930.83990.032*
H460.46400.98020.68280.030*
H620.64600.75480.38050.029*
H630.62590.71380.20160.030*
H640.42460.59210.02740.034*
H650.19380.47440.02810.038*
H660.05770.44340.08610.035*
H670.14910.52220.25800.030*
H200.89040.79750.28480.033*
H21A1.11460.89560.34900.055*
H21B1.18290.97570.27580.055*
H21C1.21570.82740.28920.055*
H22A0.95020.78670.05100.057*
H22B1.11430.77250.09460.057*
H22C1.06700.91750.08850.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0242 (9)0.0240 (8)0.0187 (8)0.0008 (7)0.0062 (7)0.0050 (7)
C110.0226 (10)0.0206 (10)0.0249 (10)0.0038 (8)0.0022 (8)0.0065 (8)
C120.0241 (10)0.0268 (11)0.0297 (11)0.0029 (8)0.0063 (9)0.0063 (9)
C130.0235 (11)0.0283 (11)0.0455 (14)0.0002 (9)0.0069 (10)0.0102 (10)
C140.0294 (11)0.0239 (11)0.0376 (13)0.0006 (9)0.0014 (10)0.0009 (9)
C150.0354 (12)0.0261 (11)0.0314 (12)0.0033 (9)0.0064 (10)0.0006 (9)
C160.0288 (11)0.0240 (10)0.0294 (11)0.0015 (9)0.0081 (9)0.0036 (9)
N20.0314 (9)0.0278 (9)0.0188 (9)0.0039 (7)0.0085 (7)0.0052 (7)
C30.0286 (11)0.0224 (10)0.0212 (10)0.0052 (8)0.0060 (8)0.0061 (8)
C310.0379 (12)0.0332 (12)0.0217 (11)0.0027 (10)0.0094 (9)0.0044 (9)
C3A0.0255 (10)0.0215 (10)0.0190 (10)0.0052 (8)0.0058 (8)0.0047 (8)
C40.0223 (10)0.0212 (10)0.0207 (10)0.0063 (8)0.0031 (8)0.0045 (8)
C410.0223 (10)0.0222 (10)0.0202 (10)0.0015 (8)0.0054 (8)0.0024 (8)
C420.0345 (12)0.0222 (10)0.0247 (11)0.0050 (9)0.0040 (9)0.0023 (8)
C430.0293 (11)0.0308 (11)0.0229 (11)0.0024 (9)0.0021 (9)0.0042 (9)
C440.0252 (10)0.0278 (11)0.0226 (10)0.0007 (8)0.0083 (8)0.0006 (8)
C4410.0382 (13)0.0359 (12)0.0264 (12)0.0025 (10)0.0084 (10)0.0058 (9)
C450.0308 (11)0.0198 (10)0.0297 (11)0.0014 (8)0.0105 (9)0.0001 (8)
C460.0252 (10)0.0242 (10)0.0250 (11)0.0034 (8)0.0060 (8)0.0060 (8)
C50.0201 (10)0.0214 (10)0.0218 (10)0.0023 (8)0.0039 (8)0.0048 (8)
C510.0248 (11)0.0300 (11)0.0208 (10)0.0028 (9)0.0044 (8)0.0035 (8)
N510.0334 (10)0.0355 (11)0.0292 (10)0.0080 (9)0.0067 (8)0.0019 (8)
C60.0182 (9)0.0217 (10)0.0221 (10)0.0034 (8)0.0044 (8)0.0052 (8)
C610.0244 (10)0.0200 (9)0.0196 (10)0.0048 (8)0.0061 (8)0.0043 (8)
C620.0265 (10)0.0234 (10)0.0212 (10)0.0039 (8)0.0055 (8)0.0041 (8)
N630.0261 (9)0.0277 (9)0.0252 (9)0.0033 (7)0.0112 (7)0.0082 (7)
C63A0.0259 (10)0.0203 (10)0.0220 (10)0.0051 (8)0.0067 (8)0.0053 (8)
C640.0367 (12)0.0290 (11)0.0216 (11)0.0067 (9)0.0122 (9)0.0060 (9)
C650.0411 (13)0.0330 (12)0.0187 (10)0.0060 (10)0.0057 (9)0.0035 (9)
C660.0275 (11)0.0314 (11)0.0245 (11)0.0002 (9)0.0028 (9)0.0037 (9)
C670.0258 (10)0.0257 (10)0.0220 (10)0.0028 (8)0.0057 (8)0.0037 (8)
C67A0.0277 (10)0.0182 (9)0.0196 (10)0.0046 (8)0.0083 (8)0.0043 (8)
N70.0219 (8)0.0232 (8)0.0194 (8)0.0029 (7)0.0055 (7)0.0037 (7)
C7A0.0216 (10)0.0209 (10)0.0215 (10)0.0037 (8)0.0038 (8)0.0040 (8)
N200.0248 (9)0.0300 (9)0.0288 (10)0.0012 (7)0.0073 (7)0.0001 (8)
C200.0303 (11)0.0267 (11)0.0245 (11)0.0006 (9)0.0087 (9)0.0032 (9)
O200.0256 (8)0.0430 (9)0.0276 (8)0.0043 (7)0.0071 (6)0.0037 (7)
C210.0281 (12)0.0351 (12)0.0403 (14)0.0009 (10)0.0014 (10)0.0021 (10)
C220.0359 (13)0.0468 (14)0.0330 (13)0.0022 (11)0.0164 (10)0.0021 (11)
Geometric parameters (Å, º) top
N1—C7A1.369 (2)C45—H450.95
N1—N21.384 (2)C46—H460.95
N1—C111.420 (2)C5—C61.432 (3)
C11—C161.389 (3)C5—C511.433 (3)
C11—C121.392 (3)C51—N511.150 (3)
C12—C131.384 (3)C6—N71.337 (2)
C12—H120.95C6—C611.460 (3)
C13—C141.380 (3)C61—C621.378 (3)
C13—H130.95C61—C67A1.442 (3)
C14—C151.382 (3)C62—N631.358 (2)
C14—H140.95C62—H620.95
C15—C161.387 (3)N63—C63A1.378 (2)
C15—H150.95N63—H630.88
C16—H160.95C63A—C641.391 (3)
N2—C31.316 (3)C63A—C67A1.411 (3)
C3—C3A1.435 (3)C64—C651.376 (3)
C3—C311.493 (3)C64—H640.95
C31—H31A0.98C65—C661.404 (3)
C31—H31B0.98C65—H650.95
C31—H31C0.98C66—C671.379 (3)
C3A—C7A1.405 (3)C66—H660.95
C3A—C41.406 (3)C67—C67A1.406 (3)
C4—C51.398 (3)C67—H670.95
C4—C411.487 (3)N7—C7A1.335 (2)
C41—C461.389 (3)N20—C201.324 (3)
C41—C421.396 (3)N20—C221.445 (3)
C42—C431.384 (3)N20—C211.456 (3)
C42—H420.95C20—O201.235 (2)
C43—C441.388 (3)C20—H200.95
C43—H430.95C21—H21A0.98
C44—C451.388 (3)C21—H21B0.98
C44—C4411.512 (3)C21—H21C0.98
C441—H44A0.98C22—H22A0.98
C441—H44B0.98C22—H22B0.98
C441—H44C0.98C22—H22C0.98
C45—C461.384 (3)
C7A—N1—N2110.04 (15)C45—C46—H46119.9
C7A—N1—C11130.79 (16)C41—C46—H46119.9
N2—N1—C11119.17 (15)C4—C5—C6121.70 (17)
C16—C11—C12120.13 (18)C4—C5—C51119.69 (17)
C16—C11—N1121.24 (17)C6—C5—C51118.61 (17)
C12—C11—N1118.63 (18)N51—C51—C5177.6 (2)
C13—C12—C11119.6 (2)N7—C6—C5121.65 (17)
C13—C12—H12120.2N7—C6—C61114.18 (16)
C11—C12—H12120.2C5—C6—C61124.17 (17)
C14—C13—C12120.7 (2)C62—C61—C67A105.76 (17)
C14—C13—H13119.6C62—C61—C6128.65 (18)
C12—C13—H13119.6C67A—C61—C6125.12 (17)
C13—C14—C15119.3 (2)N63—C62—C61110.67 (17)
C13—C14—H14120.3N63—C62—H62124.7
C15—C14—H14120.3C61—C62—H62124.7
C14—C15—C16121.0 (2)C62—N63—C63A108.97 (16)
C14—C15—H15119.5C62—N63—H63125.5
C16—C15—H15119.5C63A—N63—H63125.5
C15—C16—C11119.19 (19)N63—C63A—C64129.25 (18)
C15—C16—H16120.4N63—C63A—C67A107.65 (16)
C11—C16—H16120.4C64—C63A—C67A123.10 (18)
C3—N2—N1107.57 (16)C65—C64—C63A117.41 (19)
N2—C3—C3A110.37 (17)C65—C64—H64121.3
N2—C3—C31119.09 (18)C63A—C64—H64121.3
C3A—C3—C31130.51 (18)C64—C65—C66120.81 (19)
C3—C31—H31A109.5C64—C65—H65119.6
C3—C31—H31B109.5C66—C65—H65119.6
H31A—C31—H31B109.5C67—C66—C65121.69 (19)
C3—C31—H31C109.5C67—C66—H66119.2
H31A—C31—H31C109.5C65—C66—H66119.2
H31B—C31—H31C109.5C66—C67—C67A118.87 (19)
C7A—C3A—C4117.53 (17)C66—C67—H67120.6
C7A—C3A—C3104.80 (17)C67A—C67—H67120.6
C4—C3A—C3137.41 (18)C67—C67A—C63A118.07 (17)
C5—C4—C3A116.03 (17)C67—C67A—C61134.97 (18)
C5—C4—C41122.95 (17)C63A—C67A—C61106.96 (17)
C3A—C4—C41121.02 (17)C7A—N7—C6115.80 (16)
C46—C41—C42118.23 (18)N7—C7A—N1125.53 (17)
C46—C41—C4122.10 (17)N7—C7A—C3A127.24 (17)
C42—C41—C4119.64 (17)N1—C7A—C3A107.18 (16)
C43—C42—C41121.08 (19)C20—N20—C22121.64 (18)
C43—C42—H42119.5C20—N20—C21121.19 (18)
C41—C42—H42119.5C22—N20—C21117.17 (18)
C42—C43—C44120.76 (19)O20—C20—N20125.2 (2)
C42—C43—H43119.6O20—C20—H20117.4
C44—C43—H43119.6N20—C20—H20117.4
C45—C44—C43117.86 (18)N20—C21—H21A109.5
C45—C44—C441121.62 (18)N20—C21—H21B109.5
C43—C44—C441120.52 (19)H21A—C21—H21B109.5
C44—C441—H44A109.5N20—C21—H21C109.5
C44—C441—H44B109.5H21A—C21—H21C109.5
H44A—C441—H44B109.5H21B—C21—H21C109.5
C44—C441—H44C109.5N20—C22—H22A109.5
H44A—C441—H44C109.5N20—C22—H22B109.5
H44B—C441—H44C109.5H22A—C22—H22B109.5
C46—C45—C44121.87 (18)N20—C22—H22C109.5
C46—C45—H45119.1H22A—C22—H22C109.5
C44—C45—H45119.1H22B—C22—H22C109.5
C45—C46—C41120.17 (18)
C7A—N1—C11—C1611.4 (3)C4—C5—C6—N72.0 (3)
N2—N1—C11—C16169.71 (17)C51—C5—C6—N7177.35 (17)
C7A—N1—C11—C12169.39 (18)C4—C5—C6—C61177.64 (17)
N2—N1—C11—C129.5 (3)C51—C5—C6—C613.0 (3)
C16—C11—C12—C130.3 (3)N7—C6—C61—C62150.40 (19)
N1—C11—C12—C13179.51 (18)C5—C6—C61—C6229.3 (3)
C11—C12—C13—C141.6 (3)N7—C6—C61—C67A20.5 (3)
C12—C13—C14—C152.0 (3)C5—C6—C61—C67A159.76 (18)
C13—C14—C15—C160.4 (3)C67A—C61—C62—N630.0 (2)
C14—C15—C16—C111.5 (3)C6—C61—C62—N63172.28 (18)
C12—C11—C16—C151.8 (3)C61—C62—N63—C63A0.2 (2)
N1—C11—C16—C15178.97 (18)C62—N63—C63A—C64179.02 (19)
C7A—N1—N2—C31.3 (2)C62—N63—C63A—C67A0.3 (2)
C11—N1—N2—C3179.60 (16)N63—C63A—C64—C65178.79 (19)
N1—N2—C3—C3A0.0 (2)C67A—C63A—C64—C650.5 (3)
N1—N2—C3—C31178.33 (16)C63A—C64—C65—C661.8 (3)
N2—C3—C3A—C7A1.2 (2)C64—C65—C66—C671.1 (3)
C31—C3—C3A—C7A176.9 (2)C65—C66—C67—C67A1.0 (3)
N2—C3—C3A—C4174.9 (2)C66—C67—C67A—C63A2.2 (3)
C31—C3—C3A—C43.2 (4)C66—C67—C67A—C61178.6 (2)
C7A—C3A—C4—C51.4 (3)N63—C63A—C67A—C67179.03 (16)
C3—C3A—C4—C5171.7 (2)C64—C63A—C67A—C671.6 (3)
C7A—C3A—C4—C41179.38 (17)N63—C63A—C67A—C610.4 (2)
C3—C3A—C4—C417.5 (3)C64—C63A—C67A—C61179.05 (17)
C5—C4—C41—C4658.5 (3)C62—C61—C67A—C67179.0 (2)
C3A—C4—C41—C46120.6 (2)C6—C61—C67A—C678.3 (3)
C5—C4—C41—C42123.4 (2)C62—C61—C67A—C63A0.2 (2)
C3A—C4—C41—C4257.4 (3)C6—C61—C67A—C63A172.42 (17)
C46—C41—C42—C431.3 (3)C5—C6—N7—C7A0.1 (3)
C4—C41—C42—C43176.82 (19)C61—C6—N7—C7A179.59 (16)
C41—C42—C43—C440.3 (3)C6—N7—C7A—N1175.99 (17)
C42—C43—C44—C451.6 (3)C6—N7—C7A—C3A1.1 (3)
C42—C43—C44—C441177.70 (19)N2—N1—C7A—N7175.59 (17)
C43—C44—C45—C461.4 (3)C11—N1—C7A—N73.4 (3)
C441—C44—C45—C46177.96 (19)N2—N1—C7A—C3A2.0 (2)
C44—C45—C46—C410.2 (3)C11—N1—C7A—C3A179.00 (18)
C42—C41—C46—C451.5 (3)C4—C3A—C7A—N70.5 (3)
C4—C41—C46—C45176.50 (18)C3—C3A—C7A—N7175.66 (18)
C3A—C4—C5—C62.6 (3)C4—C3A—C7A—N1177.08 (16)
C41—C4—C5—C6178.20 (17)C3—C3A—C7A—N11.9 (2)
C3A—C4—C5—C51176.79 (17)C22—N20—C20—O201.5 (3)
C41—C4—C5—C512.4 (3)C21—N20—C20—O20177.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N63—H63···O200.881.892.767 (2)173
C42—H42···Cgi0.952.653.514 (2)151
Symmetry code: (i) x+1, y+1, z+1.
(II) 6-(1H-indol-3-yl)-3-methyl-4-(4-methoxyphenyl)-1-phenyl-1H- pyrazolo[3,4-b]pyridine-5-carbonitrile top
Crystal data top
C29H21N5O·C3H7NOF(000) = 2224
Mr = 528.60Dx = 1.330 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6055 reflections
a = 30.303 (3) Åθ = 3.8–27.5°
b = 11.3490 (16) ŵ = 0.09 mm1
c = 20.344 (3) ÅT = 120 K
β = 131.010 (5)°Block, colourless
V = 5279.5 (12) Å30.51 × 0.49 × 0.27 mm
Z = 8
Data collection top
Bruker–Nonius KappaCCD
diffractometer
6055 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode3416 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.8°
ϕ & ω scansh = 3939
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1414
Tmin = 0.949, Tmax = 0.977l = 2626
63662 measured reflections
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.237H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1316P)2 + 4.8045P]
where P = (Fo2 + 2Fc2)/3
6055 reflections(Δ/σ)max < 0.001
365 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C29H21N5O·C3H7NOV = 5279.5 (12) Å3
Mr = 528.60Z = 8
Monoclinic, C2/cMo Kα radiation
a = 30.303 (3) ŵ = 0.09 mm1
b = 11.3490 (16) ÅT = 120 K
c = 20.344 (3) Å0.51 × 0.49 × 0.27 mm
β = 131.010 (5)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
6055 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
3416 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.977Rint = 0.074
63662 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.237H-atom parameters constrained
S = 1.07Δρmax = 0.43 e Å3
6055 reflectionsΔρmin = 0.34 e Å3
365 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.32488 (10)0.7888 (2)0.70486 (14)0.0322 (5)
C110.36448 (12)0.8849 (2)0.73863 (17)0.0321 (6)
C120.38321 (13)0.9405 (3)0.81386 (18)0.0380 (7)
C130.42035 (13)1.0364 (3)0.8457 (2)0.0435 (8)
C140.43968 (13)1.0772 (3)0.80465 (19)0.0401 (7)
C150.42110 (12)1.0207 (3)0.72984 (19)0.0385 (7)
C160.38351 (11)0.9253 (2)0.69623 (18)0.0333 (6)
N20.29659 (10)0.7677 (2)0.73639 (15)0.0343 (6)
C30.25999 (12)0.6793 (3)0.69113 (18)0.0336 (6)
C310.22399 (13)0.6345 (3)0.71148 (19)0.0400 (7)
C3A0.26325 (11)0.6392 (2)0.62731 (17)0.0304 (6)
C40.23864 (11)0.5493 (2)0.56523 (17)0.0300 (6)
C410.19147 (11)0.4709 (2)0.54415 (17)0.0297 (6)
C420.13762 (12)0.5176 (2)0.51039 (17)0.0326 (6)
C430.09360 (12)0.4440 (2)0.48931 (18)0.0330 (6)
C440.10316 (11)0.3233 (2)0.50422 (17)0.0306 (6)
O440.05704 (8)0.25804 (17)0.48253 (13)0.0379 (5)
C4410.06882 (14)0.1363 (3)0.5079 (2)0.0418 (7)
C450.15661 (12)0.2763 (3)0.53807 (18)0.0336 (6)
C460.20003 (12)0.3501 (2)0.55714 (18)0.0331 (6)
C50.26140 (11)0.5367 (2)0.52369 (17)0.0297 (6)
C510.23897 (12)0.4441 (3)0.46091 (19)0.0326 (6)
N510.22104 (10)0.3701 (2)0.41031 (16)0.0383 (6)
C60.30551 (11)0.6147 (2)0.54193 (16)0.0285 (6)
C610.33029 (11)0.6076 (2)0.49971 (17)0.0287 (6)
C620.30427 (12)0.5661 (2)0.41748 (18)0.0324 (6)
N630.33872 (10)0.5905 (2)0.39853 (15)0.0336 (6)
C63A0.38834 (12)0.6484 (2)0.46756 (18)0.0305 (6)
C640.43473 (12)0.6915 (3)0.47644 (19)0.0343 (6)
C650.47972 (12)0.7480 (3)0.55343 (19)0.0356 (7)
C660.47790 (12)0.7598 (2)0.62011 (18)0.0342 (6)
C670.43153 (12)0.7167 (2)0.61128 (17)0.0313 (6)
C67A0.38476 (11)0.6605 (2)0.53326 (17)0.0281 (6)
N70.32761 (9)0.7014 (2)0.60023 (14)0.0302 (5)
C7A0.30613 (11)0.7103 (2)0.64019 (17)0.0293 (6)
N200.39941 (11)0.5910 (2)0.22693 (15)0.0388 (6)
C200.36099 (14)0.6152 (3)0.2364 (2)0.0433 (8)
O200.35567 (11)0.5587 (2)0.28208 (15)0.0576 (7)
C210.40002 (17)0.6580 (3)0.1665 (2)0.0554 (9)
C220.44024 (16)0.4946 (3)0.2732 (2)0.0553 (9)
H120.37060.91300.84330.046*
H130.43281.07490.89690.052*
H140.46531.14300.82720.048*
H150.43441.04780.70120.046*
H160.37080.88760.64460.040*
H31A0.23790.66930.76630.060*
H31B0.22740.54850.71720.060*
H31C0.18300.65610.66440.060*
H420.13120.60020.50190.039*
H430.05660.47600.46450.040*
H44A0.08060.09620.47890.063*
H44B0.03350.09890.49090.063*
H44C0.10040.13060.57120.063*
H450.16340.19390.54810.040*
H460.23640.31740.57960.040*
H620.26770.52640.37990.039*
H630.33060.57220.34950.040*
H640.43570.68270.43100.041*
H650.51190.77880.56100.043*
H660.50920.79820.67260.041*
H670.43120.72500.65750.038*
H200.33590.68100.20560.052*
H21A0.36980.71910.13870.083*
H21B0.39230.60500.12190.083*
H21C0.43840.69500.19840.083*
H22A0.43220.45150.30610.083*
H22B0.48020.52560.31340.083*
H22C0.43600.44120.23140.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0328 (12)0.0364 (13)0.0322 (12)0.0006 (10)0.0234 (11)0.0011 (10)
C110.0274 (13)0.0316 (15)0.0300 (14)0.0039 (11)0.0157 (12)0.0014 (12)
C120.0391 (16)0.0396 (17)0.0346 (15)0.0002 (14)0.0239 (14)0.0037 (13)
C130.0411 (17)0.0433 (19)0.0366 (16)0.0018 (14)0.0214 (14)0.0085 (14)
C140.0374 (16)0.0315 (16)0.0389 (16)0.0026 (13)0.0196 (14)0.0047 (13)
C150.0367 (15)0.0354 (17)0.0420 (17)0.0012 (13)0.0253 (14)0.0035 (13)
C160.0304 (14)0.0339 (15)0.0311 (14)0.0002 (12)0.0183 (13)0.0042 (12)
N20.0355 (13)0.0396 (14)0.0329 (13)0.0002 (11)0.0247 (11)0.0006 (11)
C30.0344 (15)0.0365 (16)0.0325 (15)0.0033 (13)0.0230 (13)0.0032 (12)
C310.0442 (17)0.0454 (18)0.0376 (16)0.0009 (14)0.0300 (15)0.0015 (14)
C3A0.0308 (14)0.0335 (15)0.0290 (14)0.0036 (12)0.0205 (12)0.0030 (11)
C40.0287 (13)0.0304 (15)0.0295 (14)0.0043 (11)0.0185 (12)0.0053 (11)
C410.0291 (13)0.0317 (15)0.0277 (13)0.0006 (11)0.0183 (12)0.0012 (11)
C420.0390 (15)0.0281 (14)0.0333 (15)0.0023 (12)0.0249 (13)0.0029 (12)
C430.0307 (14)0.0327 (15)0.0367 (15)0.0034 (12)0.0226 (13)0.0029 (12)
C440.0323 (14)0.0325 (15)0.0316 (14)0.0002 (12)0.0230 (13)0.0024 (11)
O440.0351 (11)0.0302 (11)0.0532 (13)0.0016 (9)0.0310 (10)0.0069 (9)
C4410.0469 (17)0.0289 (15)0.0582 (19)0.0007 (13)0.0382 (16)0.0050 (14)
C450.0375 (15)0.0295 (15)0.0371 (15)0.0043 (12)0.0260 (14)0.0032 (12)
C460.0293 (14)0.0339 (16)0.0342 (15)0.0010 (12)0.0200 (13)0.0017 (12)
C50.0297 (14)0.0293 (14)0.0292 (14)0.0043 (11)0.0190 (12)0.0021 (11)
C510.0304 (14)0.0312 (15)0.0374 (15)0.0002 (12)0.0228 (13)0.0000 (13)
N510.0365 (13)0.0339 (14)0.0443 (14)0.0006 (11)0.0264 (12)0.0045 (12)
C60.0252 (13)0.0290 (14)0.0283 (13)0.0039 (11)0.0163 (12)0.0021 (11)
C610.0305 (14)0.0285 (14)0.0293 (13)0.0020 (11)0.0205 (12)0.0007 (11)
C620.0339 (15)0.0297 (15)0.0379 (15)0.0012 (12)0.0254 (13)0.0009 (12)
N630.0353 (13)0.0357 (13)0.0325 (12)0.0019 (10)0.0235 (11)0.0037 (10)
C63A0.0356 (15)0.0246 (14)0.0349 (15)0.0030 (12)0.0246 (13)0.0019 (11)
C640.0351 (15)0.0357 (16)0.0387 (15)0.0011 (12)0.0272 (14)0.0006 (13)
C650.0358 (15)0.0311 (15)0.0426 (16)0.0006 (12)0.0269 (14)0.0026 (13)
C660.0310 (14)0.0297 (15)0.0358 (15)0.0021 (12)0.0194 (13)0.0019 (12)
C670.0351 (14)0.0300 (15)0.0319 (14)0.0034 (12)0.0233 (13)0.0028 (11)
C67A0.0292 (14)0.0250 (13)0.0302 (14)0.0031 (11)0.0195 (12)0.0034 (11)
N70.0312 (12)0.0300 (12)0.0309 (12)0.0009 (10)0.0210 (11)0.0022 (10)
C7A0.0291 (13)0.0287 (14)0.0278 (13)0.0030 (11)0.0176 (12)0.0006 (11)
N200.0413 (14)0.0418 (15)0.0374 (13)0.0034 (11)0.0276 (12)0.0005 (11)
C200.0427 (17)0.051 (2)0.0362 (16)0.0015 (15)0.0260 (15)0.0072 (14)
O200.0665 (16)0.0723 (17)0.0502 (14)0.0131 (13)0.0454 (13)0.0142 (12)
C210.070 (2)0.054 (2)0.059 (2)0.0045 (18)0.049 (2)0.0024 (18)
C220.057 (2)0.047 (2)0.055 (2)0.0131 (17)0.0340 (18)0.0009 (17)
Geometric parameters (Å, º) top
N1—C7A1.366 (3)C45—C461.383 (4)
N1—N21.388 (3)C45—H450.95
N1—C111.421 (4)C46—H460.95
C11—C121.387 (4)C5—C61.435 (4)
C11—C161.393 (4)C5—C511.435 (4)
C12—C131.384 (4)C51—N511.151 (3)
C12—H120.95C6—N71.335 (3)
C13—C141.377 (5)C6—C611.468 (4)
C13—H130.95C61—C621.383 (4)
C14—C151.386 (4)C61—C67A1.439 (4)
C14—H140.95C62—N631.358 (3)
C15—C161.384 (4)C62—H620.95
C15—H150.95N63—C63A1.376 (4)
C16—H160.95N63—H630.88
N2—C31.321 (4)C63A—C641.384 (4)
C3—C3A1.439 (4)C63A—C67A1.417 (4)
C3—C311.487 (4)C64—C651.386 (4)
C31—H31A0.98C64—H640.95
C31—H31B0.98C65—C661.400 (4)
C31—H31C0.98C65—H650.95
C3A—C41.399 (4)C66—C671.384 (4)
C3A—C7A1.400 (4)C66—H660.95
C4—C51.405 (4)C67—C67A1.408 (4)
C4—C411.488 (4)C67—H670.95
C41—C461.388 (4)N7—C7A1.338 (3)
C41—C421.395 (4)N20—C201.328 (4)
C42—C431.382 (4)N20—C221.444 (4)
C42—H420.95N20—C211.455 (4)
C43—C441.392 (4)C20—O201.223 (4)
C43—H430.95C20—H200.95
C44—O441.374 (3)C21—H21A0.98
C44—C451.385 (4)C21—H21B0.98
O44—C4411.436 (3)C21—H21C0.98
C441—H44A0.98C22—H22A0.98
C441—H44B0.98C22—H22B0.98
C441—H44C0.98C22—H22C0.98
C7A—N1—N2109.9 (2)C45—C46—C41121.3 (3)
C7A—N1—C11130.7 (2)C45—C46—H46119.3
N2—N1—C11119.4 (2)C41—C46—H46119.3
C12—C11—C16119.8 (3)C4—C5—C6121.5 (2)
C12—C11—N1119.2 (3)C4—C5—C51118.5 (2)
C16—C11—N1121.0 (2)C6—C5—C51119.9 (2)
C13—C12—C11119.5 (3)N51—C51—C5179.6 (3)
C13—C12—H12120.2N7—C6—C5121.6 (2)
C11—C12—H12120.2N7—C6—C61114.2 (2)
C14—C13—C12121.3 (3)C5—C6—C61124.2 (2)
C14—C13—H13119.3C62—C61—C67A106.4 (2)
C12—C13—H13119.3C62—C61—C6128.5 (2)
C13—C14—C15118.8 (3)C67A—C61—C6124.6 (2)
C13—C14—H14120.6N63—C62—C61109.9 (2)
C15—C14—H14120.6N63—C62—H62125.1
C16—C15—C14121.0 (3)C61—C62—H62125.1
C16—C15—H15119.5C62—N63—C63A109.7 (2)
C14—C15—H15119.5C62—N63—H63125.2
C15—C16—C11119.5 (3)C63A—N63—H63125.2
C15—C16—H16120.2N63—C63A—C64129.7 (3)
C11—C16—H16120.2N63—C63A—C67A107.5 (2)
C3—N2—N1107.4 (2)C64—C63A—C67A122.9 (3)
N2—C3—C3A110.2 (2)C63A—C64—C65118.2 (3)
N2—C3—C31119.9 (2)C63A—C64—H64120.9
C3A—C3—C31129.8 (3)C65—C64—H64120.9
C3—C31—H31A109.5C64—C65—C66120.3 (3)
C3—C31—H31B109.5C64—C65—H65119.8
H31A—C31—H31B109.5C66—C65—H65119.8
C3—C31—H31C109.5C67—C66—C65121.5 (3)
H31A—C31—H31C109.5C67—C66—H66119.2
H31B—C31—H31C109.5C65—C66—H66119.2
C4—C3A—C7A117.9 (2)C66—C67—C67A119.5 (2)
C4—C3A—C3137.2 (3)C66—C67—H67120.3
C7A—C3A—C3104.7 (2)C67A—C67—H67120.3
C3A—C4—C5115.8 (2)C67—C67A—C63A117.6 (2)
C3A—C4—C41122.6 (2)C67—C67A—C61135.7 (2)
C5—C4—C41121.6 (2)C63A—C67A—C61106.6 (2)
C46—C41—C42118.8 (3)C6—N7—C7A115.8 (2)
C46—C41—C4120.8 (2)N7—C7A—N1125.0 (2)
C42—C41—C4120.5 (2)N7—C7A—C3A127.2 (2)
C43—C42—C41120.1 (3)N1—C7A—C3A107.7 (2)
C43—C42—H42119.9C20—N20—C22121.3 (3)
C41—C42—H42119.9C20—N20—C21120.8 (3)
C42—C43—C44120.5 (3)C22—N20—C21117.8 (3)
C42—C43—H43119.8O20—C20—N20124.5 (3)
C44—C43—H43119.8O20—C20—H20117.8
O44—C44—C45124.3 (3)N20—C20—H20117.8
O44—C44—C43116.0 (2)N20—C21—H21A109.5
C45—C44—C43119.7 (3)N20—C21—H21B109.5
C44—O44—C441116.3 (2)H21A—C21—H21B109.5
O44—C441—H44A109.5N20—C21—H21C109.5
O44—C441—H44B109.5H21A—C21—H21C109.5
H44A—C441—H44B109.5H21B—C21—H21C109.5
O44—C441—H44C109.5N20—C22—H22A109.5
H44A—C441—H44C109.5N20—C22—H22B109.5
H44B—C441—H44C109.5H22A—C22—H22B109.5
C46—C45—C44119.5 (3)N20—C22—H22C109.5
C46—C45—H45120.2H22A—C22—H22C109.5
C44—C45—H45120.2H22B—C22—H22C109.5
C7A—N1—C11—C12170.2 (3)C41—C4—C5—C511.3 (4)
N2—N1—C11—C1213.1 (4)C4—C5—C6—N71.2 (4)
C7A—N1—C11—C1611.3 (4)C51—C5—C6—N7179.6 (2)
N2—N1—C11—C16165.4 (2)C4—C5—C6—C61178.8 (2)
C16—C11—C12—C130.5 (4)C51—C5—C6—C610.3 (4)
N1—C11—C12—C13178.0 (3)N7—C6—C61—C62151.4 (3)
C11—C12—C13—C140.7 (5)C5—C6—C61—C6228.6 (4)
C12—C13—C14—C150.2 (5)N7—C6—C61—C67A18.7 (4)
C13—C14—C15—C160.4 (5)C5—C6—C61—C67A161.3 (3)
C14—C15—C16—C110.6 (4)C67A—C61—C62—N630.4 (3)
C12—C11—C16—C150.1 (4)C6—C61—C62—N63171.1 (3)
N1—C11—C16—C15178.6 (2)C61—C62—N63—C63A0.2 (3)
C7A—N1—N2—C31.2 (3)C62—N63—C63A—C64178.8 (3)
C11—N1—N2—C3176.2 (2)C62—N63—C63A—C67A0.1 (3)
N1—N2—C3—C3A0.1 (3)N63—C63A—C64—C65179.4 (3)
N1—N2—C3—C31178.7 (2)C67A—C63A—C64—C650.6 (4)
N2—C3—C3A—C4176.4 (3)C63A—C64—C65—C660.4 (4)
C31—C3—C3A—C42.3 (5)C64—C65—C66—C670.5 (4)
N2—C3—C3A—C7A1.3 (3)C65—C66—C67—C67A0.5 (4)
C31—C3—C3A—C7A177.4 (3)C66—C67—C67A—C63A1.4 (4)
C7A—C3A—C4—C52.2 (4)C66—C67—C67A—C61178.8 (3)
C3—C3A—C4—C5172.4 (3)N63—C63A—C67A—C67179.4 (2)
C7A—C3A—C4—C41178.0 (2)C64—C63A—C67A—C671.5 (4)
C3—C3A—C4—C417.3 (5)N63—C63A—C67A—C610.4 (3)
C3A—C4—C41—C46119.0 (3)C64—C63A—C67A—C61178.7 (2)
C5—C4—C41—C4660.7 (4)C62—C61—C67A—C67179.3 (3)
C3A—C4—C41—C4261.4 (4)C6—C61—C67A—C678.8 (5)
C5—C4—C41—C42118.9 (3)C62—C61—C67A—C63A0.5 (3)
C46—C41—C42—C430.9 (4)C6—C61—C67A—C63A171.5 (2)
C4—C41—C42—C43178.7 (2)C5—C6—N7—C7A0.2 (4)
C41—C42—C43—C442.2 (4)C61—C6—N7—C7A179.8 (2)
C42—C43—C44—O44178.8 (2)C6—N7—C7A—N1176.5 (2)
C42—C43—C44—C451.9 (4)C6—N7—C7A—C3A0.2 (4)
C45—C44—O44—C4418.5 (4)N2—N1—C7A—N7175.2 (2)
C43—C44—O44—C441172.3 (2)C11—N1—C7A—N77.8 (4)
O44—C44—C45—C46179.6 (2)N2—N1—C7A—C3A2.0 (3)
C43—C44—C45—C460.4 (4)C11—N1—C7A—C3A174.9 (3)
C44—C45—C46—C410.9 (4)C4—C3A—C7A—N71.0 (4)
C42—C41—C46—C450.6 (4)C3—C3A—C7A—N7175.2 (3)
C4—C41—C46—C45179.8 (2)C4—C3A—C7A—N1178.2 (2)
C3A—C4—C5—C62.3 (4)C3—C3A—C7A—N12.0 (3)
C41—C4—C5—C6177.9 (2)C22—N20—C20—O201.7 (5)
C3A—C4—C5—C51178.5 (2)C21—N20—C20—O20175.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N63—H63···O200.881.962.758 (3)149
C42—H42···Cgi0.952.683.558 (3)154
C46—H46···N51ii0.952.433.213 (4)140
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x+1/2, y+1/2, z+1.
(III) 6-(1H-indol-3-yl)-3-methyl-1-phenyl-4-(3,4,5-trimethoxyphenyl)-1H- pyrazolo[3,4-b]pyridine-5-carbonitrile top
Crystal data top
C31H25N5O3Z = 2
Mr = 515.56F(000) = 540
Triclinic, P1Dx = 1.346 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8241 (10) ÅCell parameters from 5825 reflections
b = 11.9901 (9) Åθ = 3.1–27.5°
c = 12.9130 (17) ŵ = 0.09 mm1
α = 99.372 (9)°T = 120 K
β = 108.822 (12)°Block, colourless
γ = 90.994 (7)°0.38 × 0.20 × 0.18 mm
V = 1272.3 (3) Å3
Data collection top
Bruker–Nonius KappaCCD
diffractometer
5825 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode3165 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ & ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1515
Tmin = 0.960, Tmax = 0.984l = 1616
31225 measured reflections
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0677P)2 + 0.2687P]
where P = (Fo2 + 2Fc2)/3
5825 reflections(Δ/σ)max = 0.001
356 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C31H25N5O3γ = 90.994 (7)°
Mr = 515.56V = 1272.3 (3) Å3
Triclinic, P1Z = 2
a = 8.8241 (10) ÅMo Kα radiation
b = 11.9901 (9) ŵ = 0.09 mm1
c = 12.9130 (17) ÅT = 120 K
α = 99.372 (9)°0.38 × 0.20 × 0.18 mm
β = 108.822 (12)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
5825 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
3165 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.984Rint = 0.075
31225 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.06Δρmax = 0.27 e Å3
5825 reflectionsΔρmin = 0.35 e Å3
356 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.8288 (2)0.55082 (15)0.57478 (15)0.0208 (4)
C110.9416 (3)0.49719 (18)0.65428 (18)0.0211 (5)
C120.9807 (3)0.5419 (2)0.76630 (19)0.0263 (6)
C131.0826 (3)0.4863 (2)0.8447 (2)0.0325 (6)
C141.1465 (3)0.3881 (2)0.8109 (2)0.0310 (6)
C151.1108 (3)0.3464 (2)0.6982 (2)0.0266 (6)
C161.0081 (3)0.40045 (19)0.61969 (19)0.0227 (5)
N20.8238 (2)0.66726 (15)0.59466 (15)0.0228 (5)
C30.7047 (3)0.69342 (18)0.51153 (19)0.0217 (5)
C310.6765 (3)0.81545 (18)0.5070 (2)0.0275 (6)
C3A0.6254 (3)0.59281 (18)0.43482 (18)0.0188 (5)
C40.5023 (3)0.56642 (18)0.33228 (18)0.0191 (5)
C410.4069 (2)0.65372 (17)0.27670 (18)0.0183 (5)
C420.3253 (3)0.72433 (18)0.33320 (19)0.0208 (5)
C430.2327 (3)0.80450 (18)0.28112 (18)0.0194 (5)
O430.14951 (19)0.87919 (13)0.32893 (13)0.0271 (4)
C4310.1773 (3)0.8859 (2)0.44543 (19)0.0302 (6)
C440.2193 (3)0.81218 (18)0.17206 (18)0.0210 (5)
O440.13111 (18)0.89568 (12)0.12391 (13)0.0256 (4)
C4410.0060 (3)0.8548 (2)0.0261 (2)0.0355 (7)
C450.3052 (3)0.74285 (19)0.11722 (18)0.0221 (5)
O450.29257 (19)0.76236 (14)0.01335 (13)0.0310 (4)
C4510.4007 (3)0.7087 (2)0.0378 (2)0.0353 (6)
C460.3984 (3)0.66287 (18)0.16897 (18)0.0206 (5)
C50.4756 (3)0.45107 (18)0.28397 (18)0.0196 (5)
C510.3603 (3)0.41607 (18)0.1744 (2)0.0214 (5)
N510.2724 (2)0.38747 (16)0.08551 (17)0.0309 (5)
C60.5638 (3)0.36616 (18)0.33867 (18)0.0195 (5)
C610.5269 (3)0.24616 (18)0.29019 (18)0.0208 (5)
C620.3775 (3)0.18915 (18)0.24427 (18)0.0235 (5)
N630.3908 (2)0.07754 (15)0.20989 (16)0.0272 (5)
C63A0.5513 (3)0.05854 (19)0.23097 (19)0.0244 (5)
C640.6229 (3)0.0399 (2)0.2067 (2)0.0326 (6)
C650.7872 (3)0.0324 (2)0.2320 (2)0.0349 (7)
C660.8778 (3)0.0711 (2)0.2787 (2)0.0293 (6)
C670.8076 (3)0.16856 (19)0.30425 (19)0.0244 (5)
C67A0.6411 (3)0.16309 (18)0.28160 (18)0.0214 (5)
N70.6836 (2)0.39235 (15)0.43588 (15)0.0207 (4)
C7A0.7109 (3)0.50362 (18)0.47888 (18)0.0190 (5)
H120.93800.61010.78940.032*
H131.10840.51590.92170.039*
H141.21450.34930.86450.037*
H151.15740.28020.67480.032*
H160.98340.37140.54270.027*
H31A0.58020.83380.52650.041*
H31B0.66150.82930.43170.041*
H31C0.76930.86320.55990.041*
H420.33280.71790.40700.025*
H43A0.15130.81140.45980.045*
H43B0.10920.94110.46920.045*
H43C0.29040.90990.48700.045*
H44A0.02780.84420.03990.053*
H44B0.08740.91030.01860.053*
H44C0.05120.78240.03320.053*
H45A0.51160.73140.01020.053*
H45B0.38310.73180.10990.053*
H45C0.38150.62620.04860.053*
H460.45570.61490.13130.025*
H620.27900.22290.23750.028*
H630.31010.02560.17910.033*
H640.56080.10990.17370.039*
H650.83980.09870.21760.042*
H660.99050.07410.29310.035*
H670.87080.23820.33660.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0214 (10)0.0175 (10)0.0211 (10)0.0033 (8)0.0030 (8)0.0043 (8)
C110.0175 (12)0.0221 (12)0.0232 (13)0.0003 (10)0.0052 (10)0.0060 (10)
C120.0236 (13)0.0263 (13)0.0258 (13)0.0053 (11)0.0047 (11)0.0021 (11)
C130.0327 (15)0.0419 (16)0.0172 (13)0.0042 (12)0.0015 (11)0.0024 (11)
C140.0245 (14)0.0363 (15)0.0298 (15)0.0036 (11)0.0033 (11)0.0112 (12)
C150.0214 (13)0.0296 (14)0.0301 (14)0.0049 (11)0.0079 (11)0.0099 (11)
C160.0228 (13)0.0252 (13)0.0209 (12)0.0007 (10)0.0084 (10)0.0040 (10)
N20.0242 (11)0.0191 (10)0.0250 (11)0.0011 (8)0.0080 (9)0.0037 (8)
C30.0215 (13)0.0221 (13)0.0218 (12)0.0029 (10)0.0072 (10)0.0045 (10)
C310.0298 (14)0.0192 (12)0.0272 (14)0.0004 (10)0.0021 (11)0.0016 (10)
C3A0.0193 (12)0.0165 (12)0.0220 (12)0.0024 (9)0.0081 (10)0.0040 (9)
C40.0179 (12)0.0213 (12)0.0209 (12)0.0019 (9)0.0088 (10)0.0069 (10)
C410.0161 (12)0.0177 (12)0.0191 (12)0.0009 (9)0.0037 (9)0.0023 (9)
C420.0227 (12)0.0192 (12)0.0198 (12)0.0007 (10)0.0053 (10)0.0052 (10)
C430.0169 (12)0.0176 (12)0.0232 (13)0.0009 (9)0.0062 (10)0.0029 (10)
O430.0307 (9)0.0250 (9)0.0285 (10)0.0113 (7)0.0126 (8)0.0062 (7)
C4310.0385 (15)0.0282 (14)0.0254 (14)0.0076 (12)0.0139 (12)0.0017 (11)
C440.0209 (12)0.0152 (12)0.0242 (13)0.0024 (9)0.0020 (10)0.0068 (10)
O440.0234 (9)0.0218 (9)0.0284 (9)0.0038 (7)0.0012 (7)0.0101 (7)
C4410.0306 (15)0.0326 (15)0.0332 (15)0.0022 (12)0.0038 (12)0.0071 (12)
C450.0254 (13)0.0228 (12)0.0184 (12)0.0001 (10)0.0060 (10)0.0073 (10)
O450.0363 (10)0.0372 (10)0.0240 (9)0.0114 (8)0.0116 (8)0.0137 (8)
C4510.0428 (16)0.0449 (16)0.0244 (14)0.0102 (13)0.0179 (12)0.0090 (12)
C460.0216 (12)0.0198 (12)0.0217 (13)0.0040 (10)0.0087 (10)0.0038 (10)
C50.0188 (12)0.0214 (12)0.0201 (12)0.0021 (10)0.0080 (10)0.0043 (10)
C510.0224 (13)0.0166 (12)0.0247 (13)0.0034 (10)0.0064 (11)0.0046 (10)
N510.0335 (12)0.0266 (11)0.0277 (12)0.0033 (10)0.0038 (10)0.0040 (9)
C60.0201 (12)0.0188 (12)0.0203 (12)0.0009 (10)0.0081 (10)0.0023 (10)
C610.0224 (13)0.0210 (12)0.0183 (12)0.0039 (10)0.0055 (10)0.0036 (9)
C620.0248 (13)0.0206 (13)0.0246 (13)0.0048 (10)0.0065 (11)0.0059 (10)
N630.0240 (11)0.0200 (11)0.0326 (12)0.0007 (9)0.0044 (9)0.0012 (9)
C63A0.0232 (13)0.0207 (13)0.0281 (14)0.0035 (10)0.0069 (11)0.0036 (10)
C640.0303 (15)0.0195 (13)0.0422 (16)0.0012 (11)0.0065 (12)0.0002 (11)
C650.0334 (16)0.0269 (14)0.0401 (16)0.0112 (12)0.0074 (12)0.0027 (12)
C660.0216 (13)0.0317 (15)0.0310 (14)0.0064 (11)0.0039 (11)0.0050 (11)
C670.0266 (14)0.0216 (13)0.0226 (13)0.0023 (10)0.0045 (10)0.0039 (10)
C67A0.0226 (13)0.0219 (12)0.0191 (12)0.0030 (10)0.0048 (10)0.0058 (10)
N70.0212 (10)0.0200 (10)0.0209 (10)0.0011 (8)0.0068 (8)0.0038 (8)
C7A0.0175 (12)0.0213 (12)0.0193 (12)0.0016 (9)0.0079 (10)0.0024 (10)
Geometric parameters (Å, º) top
N1—C7A1.363 (3)C44—C451.394 (3)
N1—N21.382 (2)O44—C4411.446 (3)
N1—C111.427 (3)C441—H44A0.98
C11—C161.383 (3)C441—H44B0.98
C11—C121.385 (3)C441—H44C0.98
C12—C131.389 (3)C45—O451.368 (3)
C12—H120.95C45—C461.387 (3)
C13—C141.383 (3)O45—C4511.432 (3)
C13—H130.95C451—H45A0.98
C14—C151.389 (3)C451—H45B0.98
C14—H140.95C451—H45C0.98
C15—C161.382 (3)C46—H460.95
C15—H150.95C5—C61.431 (3)
C16—H160.95C5—C511.441 (3)
N2—C31.322 (3)C51—N511.151 (3)
C3—C3A1.436 (3)C6—N71.340 (3)
C3—C311.496 (3)C6—C611.458 (3)
C31—H31A0.98C61—C621.375 (3)
C31—H31B0.98C61—C67A1.446 (3)
C31—H31C0.98C62—N631.359 (3)
C3A—C41.399 (3)C62—H620.95
C3A—C7A1.409 (3)N63—C63A1.384 (3)
C4—C51.404 (3)N63—H630.88
C4—C411.485 (3)C63A—C641.386 (3)
C41—C421.388 (3)C63A—C67A1.411 (3)
C41—C461.391 (3)C64—C651.377 (4)
C42—C431.388 (3)C64—H640.95
C42—H420.95C65—C661.398 (3)
C43—O431.363 (3)C65—H650.95
C43—C441.393 (3)C66—C671.375 (3)
O43—C4311.432 (3)C66—H660.95
C431—H43A0.98C67—C67A1.401 (3)
C431—H43B0.98C67—H670.95
C431—H43C0.98N7—C7A1.345 (3)
C44—O441.383 (2)
C7A—N1—N2110.62 (17)O44—C441—H44A109.5
C7A—N1—C11129.55 (18)O44—C441—H44B109.5
N2—N1—C11119.71 (17)H44A—C441—H44B109.5
C16—C11—C12120.7 (2)O44—C441—H44C109.5
C16—C11—N1120.2 (2)H44A—C441—H44C109.5
C12—C11—N1119.09 (19)H44B—C441—H44C109.5
C11—C12—C13119.5 (2)O45—C45—C46124.4 (2)
C11—C12—H12120.2O45—C45—C44115.25 (19)
C13—C12—H12120.2C46—C45—C44120.3 (2)
C14—C13—C12120.2 (2)C45—O45—C451117.26 (18)
C14—C13—H13119.9O45—C451—H45A109.5
C12—C13—H13119.9O45—C451—H45B109.5
C13—C14—C15119.7 (2)H45A—C451—H45B109.5
C13—C14—H14120.2O45—C451—H45C109.5
C15—C14—H14120.2H45A—C451—H45C109.5
C16—C15—C14120.5 (2)H45B—C451—H45C109.5
C16—C15—H15119.7C45—C46—C41119.3 (2)
C14—C15—H15119.7C45—C46—H46120.4
C15—C16—C11119.4 (2)C41—C46—H46120.4
C15—C16—H16120.3C4—C5—C6122.00 (19)
C11—C16—H16120.3C4—C5—C51119.73 (19)
C3—N2—N1107.10 (17)C6—C5—C51118.24 (19)
N2—C3—C3A110.48 (19)N51—C51—C5177.7 (2)
N2—C3—C31119.2 (2)N7—C6—C5122.14 (19)
C3A—C3—C31130.3 (2)N7—C6—C61116.84 (19)
C3—C31—H31A109.5C5—C6—C61121.03 (19)
C3—C31—H31B109.5C62—C61—C67A106.24 (19)
H31A—C31—H31B109.5C62—C61—C6127.1 (2)
C3—C31—H31C109.5C67A—C61—C6126.6 (2)
H31A—C31—H31C109.5N63—C62—C61110.3 (2)
H31B—C31—H31C109.5N63—C62—H62124.8
C4—C3A—C7A118.15 (19)C61—C62—H62124.8
C4—C3A—C3137.1 (2)C62—N63—C63A109.21 (19)
C7A—C3A—C3104.59 (18)C62—N63—H63125.4
C3A—C4—C5115.42 (19)C63A—N63—H63125.4
C3A—C4—C41122.83 (19)N63—C63A—C64130.2 (2)
C5—C4—C41121.75 (19)N63—C63A—C67A107.50 (19)
C42—C41—C46120.9 (2)C64—C63A—C67A122.3 (2)
C42—C41—C4119.0 (2)C65—C64—C63A117.6 (2)
C46—C41—C4120.06 (19)C65—C64—H64121.2
C41—C42—C43119.6 (2)C63A—C64—H64121.2
C41—C42—H42120.2C64—C65—C66121.1 (2)
C43—C42—H42120.2C64—C65—H65119.5
O43—C43—C42124.6 (2)C66—C65—H65119.5
O43—C43—C44115.29 (19)C67—C66—C65121.5 (2)
C42—C43—C44120.1 (2)C67—C66—H66119.2
C43—O43—C431117.41 (17)C65—C66—H66119.2
O43—C431—H43A109.5C66—C67—C67A118.6 (2)
O43—C431—H43B109.5C66—C67—H67120.7
H43A—C431—H43B109.5C67A—C67—H67120.7
O43—C431—H43C109.5C67—C67A—C63A118.8 (2)
H43A—C431—H43C109.5C67—C67A—C61134.3 (2)
H43B—C431—H43C109.5C63A—C67A—C61106.71 (19)
O44—C44—C43118.7 (2)C6—N7—C7A114.83 (18)
O44—C44—C45121.3 (2)N7—C7A—N1125.50 (19)
C43—C44—C45119.81 (19)N7—C7A—C3A127.3 (2)
C44—O44—C441115.08 (17)N1—C7A—C3A107.19 (18)
C7A—N1—C11—C1637.4 (3)C44—C45—C46—C410.9 (3)
N2—N1—C11—C16147.0 (2)C42—C41—C46—C450.8 (3)
C7A—N1—C11—C12141.2 (2)C4—C41—C46—C45178.3 (2)
N2—N1—C11—C1234.4 (3)C3A—C4—C5—C62.7 (3)
C16—C11—C12—C132.6 (4)C41—C4—C5—C6178.1 (2)
N1—C11—C12—C13176.0 (2)C3A—C4—C5—C51175.1 (2)
C11—C12—C13—C141.0 (4)C41—C4—C5—C514.1 (3)
C12—C13—C14—C151.2 (4)C4—C5—C6—N74.2 (3)
C13—C14—C15—C162.0 (4)C51—C5—C6—N7173.7 (2)
C14—C15—C16—C110.4 (4)C4—C5—C6—C61176.0 (2)
C12—C11—C16—C151.9 (3)C51—C5—C6—C616.2 (3)
N1—C11—C16—C15176.7 (2)N7—C6—C61—C62134.9 (2)
C7A—N1—N2—C30.6 (2)C5—C6—C61—C6245.3 (3)
C11—N1—N2—C3176.94 (19)N7—C6—C61—C67A44.7 (3)
N1—N2—C3—C3A1.1 (2)C5—C6—C61—C67A135.2 (2)
N1—N2—C3—C31176.4 (2)C67A—C61—C62—N631.0 (3)
N2—C3—C3A—C4175.8 (3)C6—C61—C62—N63178.6 (2)
C31—C3—C3A—C41.4 (5)C61—C62—N63—C63A1.0 (3)
N2—C3—C3A—C7A1.2 (3)C62—N63—C63A—C64177.2 (2)
C31—C3—C3A—C7A175.9 (2)C62—N63—C63A—C67A0.6 (3)
C7A—C3A—C4—C50.7 (3)N63—C63A—C64—C65176.3 (2)
C3—C3A—C4—C5174.7 (2)C67A—C63A—C64—C651.1 (4)
C7A—C3A—C4—C41178.5 (2)C63A—C64—C65—C661.1 (4)
C3—C3A—C4—C414.5 (4)C64—C65—C66—C672.0 (4)
C3A—C4—C41—C4256.7 (3)C65—C66—C67—C67A0.6 (4)
C5—C4—C41—C42124.1 (2)C66—C67—C67A—C63A1.6 (3)
C3A—C4—C41—C46124.2 (2)C66—C67—C67A—C61175.6 (2)
C5—C4—C41—C4655.0 (3)N63—C63A—C67A—C67175.4 (2)
C46—C41—C42—C430.6 (3)C64—C63A—C67A—C672.5 (4)
C4—C41—C42—C43178.5 (2)N63—C63A—C67A—C610.1 (3)
C41—C42—C43—O43178.99 (19)C64—C63A—C67A—C61178.0 (2)
C41—C42—C43—C441.3 (3)C62—C61—C67A—C67173.9 (2)
C42—C43—O43—C4319.0 (3)C6—C61—C67A—C676.5 (4)
C44—C43—O43—C431171.3 (2)C62—C61—C67A—C63A0.6 (2)
O43—C43—C44—O442.7 (3)C6—C61—C67A—C63A179.0 (2)
C42—C43—C44—O44177.58 (19)C5—C6—N7—C7A1.7 (3)
O43—C43—C44—C45177.25 (19)C61—C6—N7—C7A178.42 (19)
C42—C43—C44—C453.0 (3)C6—N7—C7A—N1177.9 (2)
C43—C44—O44—C441119.0 (2)C6—N7—C7A—C3A2.0 (3)
C45—C44—O44—C44166.5 (3)N2—N1—C7A—N7179.7 (2)
O44—C44—C45—O451.3 (3)C11—N1—C7A—N74.4 (4)
C43—C44—C45—O45175.67 (19)N2—N1—C7A—C3A0.2 (2)
O44—C44—C45—C46177.23 (19)C11—N1—C7A—C3A175.7 (2)
C43—C44—C45—C462.8 (3)C4—C3A—C7A—N73.3 (3)
C46—C45—O45—C4519.7 (3)C3—C3A—C7A—N7179.1 (2)
C44—C45—O45—C451168.7 (2)C4—C3A—C7A—N1176.6 (2)
O45—C45—C46—C41177.4 (2)C3—C3A—C7A—N10.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N63—H63···O44i0.882.062.938 (2)173
Symmetry code: (i) x, y1, z.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC29H21N5·C3H7NOC29H21N5O·C3H7NOC31H25N5O3
Mr512.60528.60515.56
Crystal system, space groupTriclinic, P1Monoclinic, C2/cTriclinic, P1
Temperature (K)120120120
a, b, c (Å)9.8060 (3), 10.1820 (3), 13.818 (2)30.303 (3), 11.3490 (16), 20.344 (3)8.8241 (10), 11.9901 (9), 12.9130 (17)
α, β, γ (°)97.035 (6), 104.455 (6), 96.171 (3)90, 131.010 (5), 9099.372 (9), 108.822 (12), 90.994 (7)
V3)1312.2 (2)5279.5 (12)1272.3 (3)
Z282
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.080.090.09
Crystal size (mm)0.40 × 0.18 × 0.180.51 × 0.49 × 0.270.38 × 0.20 × 0.18
Data collection
DiffractometerBruker–Nonius KappaCCD
diffractometer
Bruker–Nonius KappaCCD
diffractometer
Bruker–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.961, 0.9850.949, 0.9770.960, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
31081, 5996, 3816 63662, 6055, 3416 31225, 5825, 3165
Rint0.0480.0740.075
(sin θ/λ)max1)0.6500.6500.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.146, 1.06 0.069, 0.237, 1.07 0.055, 0.152, 1.06
No. of reflections599660555825
No. of parameters356365356
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.310.43, 0.340.27, 0.35

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected torsion angles and bond angles (°) for compounds (I)–(III) top
Parameter(I)(II)(III)
N2—N1—C11—C129.5 (3)13.1 (4)34.4 (3)
C3A—C4—C41—C4257.4 (3)61.4 (4)-56.7 (3)
C5—C6—C61—C6229.3 (3)28.6 (4)-45.3 (3)
C42—C43—O43—C4319.0 (3)
C43—C44—O44—C441-172.3 (2)-119.0 (2)
C46—C45—O45—C451-9.7 (3)
C42—C43—O43124.6 (2)
C44—C43—O43115.29 (19)
C43—C44—O44116.0 (2)118.7 (2)
C45—C44—O44124.3 (3)121.3 (2)
C44—C45—O45115.25 (19)
C46—-C45—O45124.4 (2)
C43—O43—C431117.41 (17)
C44—O44—C441116.3 (2)115.08 (17)
C45—O45—C451117.26 (18)
Hydrogen bond parameters (Å, °) for compounds (I) - (III) top
CompoundD—H···AD—HH···AD···AD—H···A
(I)N63—H63···O200.881.892.767 (2)173
C42—H42···Cgi0.952.653.514 (3)151
(II)N63—H63···O200.881.962.757 (5)149
C42—H42···Cgii0.952.683.558 (3)154
C46—H46···N51iii0.952.433.213 (4)140
(III)N63—H63···O44iv0.882.062.939 (2)173
Symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) -x + 1/2, -y + 3/2, -z + 1; (iii) -x = 1/2, -y + 1/2, -z + 1; (iv) x, -1 + y, z.

Cg represents the centroid of the ring C63A/C64–C67/C67A.
 

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