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Hydrazone derivatives exhibit a wide range of biological activities, while pyrazolo­[3,4-b]quinoline derivatives, on the other hand, exhibit both anti­microbial and anti­viral activity, so that all new derivatives in these chemical classes are potentially of value. Dry grinding of a mixture of 2-chloro­quinoline-3-carbaldehyde and 4-methyl­phenyl­hydrazinium chloride gives (E)-1-[(2-chloro­quinolin-3-yl)methyl­idene]-2-(4-methyl­phen­yl)hydrazine, C17H14ClN3, (I), while the same regents in methanol in the presence of sodium cyano­borohydride give 1-(4-methyl­phen­yl)-4,9-di­hydro-1H-pyrazolo­[3,4-b]quinoline, C17H15N3, (II). The reactions between phenyl­hydrazinium chloride and either 2-chloro­quinoline-3-carbaldehyde or 2-chloro-6-methyl­quinoline-3-carbaldehyde give, respectively, 1-phenyl-1H-pyrazolo­[3,4-b]quinoline, C16H11N3, (III), which crystallizes in the space group Pbcn as a nonmerohedral twin having Z′ = 3, or 6-methyl-1-phenyl-1H-pyrazolo­[3,4-b]quinoline, C17H13N3, (IV), which crystallizes in the space group R\overline{3}. The mol­ecules of compound (I) are linked into sheets by a combination of N—H...N and C—H...π(arene) hydrogen bonds, and the mol­ecules of compound (II) are linked by a combination of N—H...N and C—H...π(arene) hydrogen bonds to form a chain of rings. In the structure of compound (III), one of the three independent mol­ecules forms chains generated by C—H...π(arene) hydrogen bonds, with a second type of mol­ecule linked to the chains by a second C—H...π(arene) hydrogen bond and the third type of mol­ecule linked to the chain by multiple π–π stacking inter­actions. A single C—H...π(arene) hydrogen bond links the mol­ecules of compound (IV) into cyclic centrosymmetric hexa­mers having \overline{3} (S6) symmetry, which are themselves linked into a three-dimensional array by π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961601278X/sk3635sup1.cif
Contains datablocks global, I, II, III, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961601278X/sk3635Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961601278X/sk3635IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961601278X/sk3635IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961601278X/sk3635IVsup5.hkl
Contains datablock IV

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601278X/sk3635Isup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601278X/sk3635IIsup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601278X/sk3635IIIsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601278X/sk3635IVsup9.cml
Supplementary material

CCDC references: 995472; 995470; 995471; 995469

Computing details top

For all compounds, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) (E)-1-[(2-Chloroquinolin-3-yl)methylidene]-2-(4-methylphenyl)hydrazine top
Crystal data top
C17H14ClN3Dx = 1.305 Mg m3
Mr = 295.76Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 3572 reflections
a = 14.730 (6) Åθ = 2.5–28.0°
b = 12.413 (5) ŵ = 0.25 mm1
c = 16.464 (5) ÅT = 296 K
V = 3010 (2) Å3Block, colourless
Z = 80.28 × 0.22 × 0.14 mm
F(000) = 1232
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer
2200 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.080
φ and ω scansθmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
h = 1919
Tmin = 0.901, Tmax = 0.966k = 1616
59891 measured reflectionsl = 2021
3467 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0574P)2 + 0.5907P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3467 reflectionsΔρmax = 0.18 e Å3
194 parametersΔρmin = 0.22 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.31620 (11)0.44493 (11)0.28740 (10)0.0500 (4)
N20.31793 (12)0.54330 (13)0.32296 (11)0.0590 (5)
H20.3735 (16)0.5762 (17)0.3265 (13)0.071*
N110.48200 (10)0.14748 (11)0.17393 (9)0.0454 (4)
C120.47319 (11)0.23884 (14)0.21195 (10)0.0415 (4)
Cl120.57326 (3)0.28779 (4)0.25668 (4)0.0642 (2)
C130.39251 (12)0.30123 (13)0.22095 (11)0.0409 (4)
C140.31606 (11)0.25532 (15)0.18813 (11)0.0467 (4)
H140.26080.29110.19260.056*
C14A0.31925 (12)0.15503 (14)0.14768 (11)0.0439 (4)
C150.24215 (14)0.10411 (17)0.11263 (13)0.0597 (5)
H150.18520.13560.11800.072*
C160.25104 (16)0.00923 (19)0.07104 (14)0.0678 (6)
H160.20010.02350.04860.081*
C170.33652 (17)0.03884 (17)0.06209 (14)0.0690 (6)
H170.34190.10250.03270.083*
C180.41181 (15)0.00635 (16)0.09589 (12)0.0594 (5)
H180.46800.02690.08990.071*
C18A0.40476 (12)0.10393 (14)0.14009 (11)0.0433 (4)
C190.39167 (13)0.40638 (14)0.26179 (12)0.0488 (5)
H190.44540.44460.26900.059*
C210.23925 (14)0.58540 (14)0.35853 (11)0.0490 (5)
C220.24187 (15)0.68640 (14)0.39531 (12)0.0545 (5)
H220.29530.72630.39470.065*
C230.16556 (16)0.72756 (16)0.43267 (12)0.0598 (6)
H230.16870.79510.45690.072*
C240.08422 (15)0.67110 (17)0.43515 (12)0.0586 (5)
C250.08211 (15)0.57136 (18)0.39657 (14)0.0666 (6)
H250.02820.53240.39600.080*
C260.15815 (14)0.52843 (17)0.35900 (13)0.0618 (6)
H260.15480.46130.33410.074*
C270.00103 (19)0.7156 (2)0.47776 (15)0.0857 (8)
H27A0.04350.73610.43810.128*
H27B0.01790.77750.50930.128*
H27C0.02400.66150.51290.128*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0590 (10)0.0375 (8)0.0535 (10)0.0021 (7)0.0000 (8)0.0056 (7)
N20.0590 (11)0.0435 (9)0.0743 (12)0.0056 (8)0.0049 (9)0.0131 (8)
N110.0442 (8)0.0450 (8)0.0470 (9)0.0061 (7)0.0026 (7)0.0002 (7)
C120.0383 (9)0.0457 (9)0.0405 (10)0.0012 (8)0.0003 (8)0.0044 (8)
Cl120.0432 (3)0.0641 (3)0.0854 (4)0.0046 (2)0.0134 (3)0.0079 (3)
C130.0401 (9)0.0402 (9)0.0424 (10)0.0001 (7)0.0031 (8)0.0017 (7)
C140.0375 (9)0.0496 (10)0.0528 (11)0.0032 (8)0.0031 (8)0.0038 (9)
C14A0.0436 (10)0.0459 (9)0.0421 (10)0.0020 (8)0.0009 (8)0.0004 (8)
C150.0478 (11)0.0647 (13)0.0666 (14)0.0034 (10)0.0078 (10)0.0095 (11)
C160.0715 (14)0.0648 (13)0.0670 (14)0.0135 (11)0.0206 (12)0.0095 (11)
C170.0873 (17)0.0510 (12)0.0687 (15)0.0074 (11)0.0220 (13)0.0150 (11)
C180.0676 (13)0.0510 (11)0.0596 (13)0.0149 (10)0.0103 (10)0.0097 (9)
C18A0.0508 (10)0.0415 (9)0.0375 (10)0.0037 (8)0.0033 (8)0.0032 (7)
C190.0484 (10)0.0401 (9)0.0577 (12)0.0035 (8)0.0012 (9)0.0033 (8)
C210.0602 (12)0.0395 (9)0.0473 (11)0.0030 (9)0.0037 (9)0.0025 (8)
C220.0719 (14)0.0401 (10)0.0514 (12)0.0015 (9)0.0058 (11)0.0017 (8)
C230.0868 (16)0.0446 (11)0.0480 (12)0.0131 (11)0.0084 (11)0.0062 (9)
C240.0683 (14)0.0605 (12)0.0469 (12)0.0191 (11)0.0123 (10)0.0080 (10)
C250.0563 (13)0.0713 (14)0.0721 (15)0.0055 (11)0.0098 (11)0.0204 (12)
C260.0645 (13)0.0493 (11)0.0716 (15)0.0005 (10)0.0060 (11)0.0208 (11)
C270.0830 (17)0.0969 (18)0.0771 (16)0.0300 (14)0.0036 (14)0.0244 (14)
Geometric parameters (Å, º) top
N1—C191.282 (2)C17—H170.9300
N1—N21.354 (2)C18—C18A1.417 (3)
N2—C211.400 (3)C18—H180.9300
N2—H20.92 (2)C19—H190.9300
N11—C121.302 (2)C21—C261.388 (3)
N11—C18A1.377 (2)C21—C221.393 (3)
C12—C131.426 (2)C22—C231.379 (3)
C12—Cl121.7562 (18)C22—H220.9300
C13—C141.373 (2)C23—C241.389 (3)
C13—C191.468 (2)C23—H230.9300
C14—C14A1.413 (3)C24—C251.392 (3)
C14—H140.9300C24—C271.516 (3)
C14A—C18A1.416 (2)C25—C261.386 (3)
C14A—C151.422 (3)C25—H250.9300
C15—C161.369 (3)C26—H260.9300
C15—H150.9300C27—H27A0.9600
C16—C171.401 (3)C27—H27B0.9600
C16—H160.9300C27—H27C0.9600
C17—C181.362 (3)
C19—N1—N2117.54 (16)N11—C18A—C18118.87 (17)
N1—N2—C21120.12 (16)C14A—C18A—C18119.57 (17)
N1—N2—H2116.5 (14)N1—C19—C13119.33 (17)
C21—N2—H2123.1 (14)N1—C19—H19120.3
C12—N11—C18A117.00 (15)C13—C19—H19120.3
N11—C12—C13127.30 (16)C26—C21—C22118.68 (19)
N11—C12—Cl12114.79 (13)C26—C21—N2121.65 (17)
C13—C12—Cl12117.90 (14)C22—C21—N2119.67 (18)
C14—C13—C12114.65 (15)C23—C22—C21120.3 (2)
C14—C13—C19122.85 (16)C23—C22—H22119.8
C12—C13—C19122.50 (16)C21—C22—H22119.8
C13—C14—C14A121.61 (16)C22—C23—C24121.95 (19)
C13—C14—H14119.2C22—C23—H23119.0
C14A—C14—H14119.2C24—C23—H23119.0
C14—C14A—C18A117.78 (16)C23—C24—C25117.1 (2)
C14—C14A—C15123.81 (17)C23—C24—C27121.8 (2)
C18A—C14A—C15118.39 (17)C25—C24—C27121.1 (2)
C16—C15—C14A120.6 (2)C26—C25—C24121.8 (2)
C16—C15—H15119.7C26—C25—H25119.1
C14A—C15—H15119.7C24—C25—H25119.1
C15—C16—C17120.3 (2)C25—C26—C21120.14 (19)
C15—C16—H16119.8C25—C26—H26119.9
C17—C16—H16119.8C21—C26—H26119.9
C18—C17—C16120.9 (2)C24—C27—H27A109.5
C18—C17—H17119.6C24—C27—H27B109.5
C16—C17—H17119.6H27A—C27—H27B109.5
C17—C18—C18A120.2 (2)C24—C27—H27C109.5
C17—C18—H18119.9H27A—C27—H27C109.5
C18A—C18—H18119.9H27B—C27—H27C109.5
N11—C18A—C14A121.56 (16)
C19—N1—N2—C21174.32 (18)C14—C14A—C18A—C18176.37 (17)
C18A—N11—C12—C131.8 (3)C15—C14A—C18A—C182.1 (3)
C18A—N11—C12—Cl12177.92 (12)C17—C18—C18A—N11179.69 (19)
N11—C12—C13—C143.0 (3)C17—C18—C18A—C14A1.1 (3)
Cl12—C12—C13—C14176.74 (13)N2—N1—C19—C13178.42 (16)
N11—C12—C13—C19176.76 (17)C14—C13—C19—N119.0 (3)
Cl12—C12—C13—C193.5 (2)C12—C13—C19—N1161.31 (17)
C12—C13—C14—C14A1.1 (3)N1—N2—C21—C260.4 (3)
C19—C13—C14—C14A178.65 (17)N1—N2—C21—C22179.67 (17)
C13—C14—C14A—C18A1.6 (3)C26—C21—C22—C231.2 (3)
C13—C14—C14A—C15179.96 (18)N2—C21—C22—C23178.11 (18)
C14—C14A—C15—C16176.95 (19)C21—C22—C23—C240.0 (3)
C18A—C14A—C15—C161.4 (3)C22—C23—C24—C251.4 (3)
C14A—C15—C16—C170.3 (3)C22—C23—C24—C27178.73 (19)
C15—C16—C17—C181.4 (4)C23—C24—C25—C261.6 (3)
C16—C17—C18—C18A0.7 (3)C27—C24—C25—C26178.5 (2)
C12—N11—C18A—C14A1.3 (2)C24—C25—C26—C210.5 (3)
C12—N11—C18A—C18177.97 (17)C22—C21—C26—C250.9 (3)
C14—C14A—C18A—N112.9 (3)N2—C21—C26—C25178.4 (2)
C15—C14A—C18A—N11178.66 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N11i0.92 (2)2.31 (2)3.219 (3)175 (2)
C16—H16···Cg1ii0.932.883.596 (3)133
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1/2, z3/2.
(II) 1-(4-Methylphenyl)-4,9-dihydro-1H-pyrazolo[3,4-b]quinoline top
Crystal data top
C17H15N3F(000) = 552
Mr = 261.32Dx = 1.279 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.6676 (17) ÅCell parameters from 3036 reflections
b = 26.571 (8) Åθ = 2.8–27.6°
c = 7.912 (2) ŵ = 0.08 mm1
β = 104.561 (9)°T = 300 K
V = 1356.7 (6) Å3Plate, colourless
Z = 40.34 × 0.22 × 0.08 mm
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer
1529 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.054
φ and ω scansθmax = 25.6°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
h = 87
Tmin = 0.992, Tmax = 0.994k = 3232
12345 measured reflectionsl = 89
2509 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.060H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.157 w = 1/[σ2(Fo2) + (0.0757P)2 + 0.1113P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2509 reflectionsΔρmax = 0.13 e Å3
185 parametersΔρmin = 0.15 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.7866 (3)0.25204 (7)0.5796 (3)0.0534 (5)
N20.9607 (3)0.25073 (9)0.5131 (3)0.0646 (6)
C30.9912 (4)0.20219 (11)0.4936 (3)0.0623 (7)
H31.09910.18960.45090.075*
C3A0.8459 (3)0.17157 (10)0.5432 (3)0.0557 (6)
C40.8093 (4)0.11650 (10)0.5386 (4)0.0745 (8)
H410.93770.09920.59250.089*
H420.76380.10540.41830.089*
C4A0.6462 (4)0.10322 (10)0.6348 (3)0.0565 (7)
C50.6082 (5)0.05338 (11)0.6632 (4)0.0740 (8)
H50.68450.02880.62360.089*
C60.4615 (6)0.03868 (12)0.7481 (4)0.0903 (10)
H60.44100.00480.76800.108*
C70.3455 (5)0.07523 (12)0.8030 (4)0.0802 (9)
H70.24490.06590.85970.096*
C80.3765 (4)0.12526 (9)0.7752 (3)0.0589 (7)
H80.29720.14950.81290.071*
C8A0.5270 (3)0.13975 (9)0.6903 (3)0.0484 (6)
N90.5542 (3)0.19129 (8)0.6648 (3)0.0533 (6)
H90.509 (4)0.2115 (9)0.737 (3)0.064*
C9A0.7211 (3)0.20479 (9)0.5997 (3)0.0499 (6)
C110.7043 (4)0.29895 (9)0.6118 (3)0.0492 (6)
C120.4944 (4)0.30852 (10)0.5550 (3)0.0574 (7)
H120.40440.28330.50030.069*
C130.4189 (4)0.35541 (11)0.5794 (3)0.0648 (7)
H130.27710.36130.54160.078*
C140.5467 (4)0.39397 (10)0.6581 (3)0.0636 (7)
C150.7561 (4)0.38321 (10)0.7179 (4)0.0677 (8)
H150.84560.40830.77430.081*
C160.8350 (4)0.33655 (10)0.6963 (3)0.0614 (7)
H160.97600.33030.73840.074*
C170.4643 (5)0.44609 (11)0.6764 (5)0.0984 (11)
H17A0.52060.46940.60780.148*
H17B0.50400.45610.79680.148*
H17C0.31590.44590.63630.148*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0450 (11)0.0683 (15)0.0497 (12)0.0035 (10)0.0169 (10)0.0006 (10)
N20.0491 (12)0.0903 (18)0.0604 (14)0.0012 (11)0.0247 (11)0.0070 (12)
C30.0478 (14)0.085 (2)0.0599 (18)0.0084 (13)0.0232 (13)0.0015 (14)
C3A0.0416 (12)0.0708 (17)0.0570 (16)0.0028 (12)0.0167 (12)0.0024 (12)
C40.0566 (16)0.081 (2)0.094 (2)0.0081 (14)0.0341 (16)0.0089 (15)
C4A0.0557 (15)0.0601 (16)0.0516 (15)0.0039 (12)0.0092 (12)0.0058 (12)
C50.082 (2)0.069 (2)0.074 (2)0.0052 (15)0.0264 (17)0.0050 (15)
C60.116 (3)0.064 (2)0.099 (3)0.0045 (18)0.041 (2)0.0020 (17)
C70.090 (2)0.079 (2)0.079 (2)0.0178 (17)0.0355 (18)0.0017 (16)
C80.0601 (15)0.0699 (18)0.0511 (15)0.0069 (13)0.0222 (13)0.0092 (12)
C8A0.0415 (12)0.0567 (16)0.0439 (14)0.0026 (11)0.0050 (11)0.0042 (11)
N90.0424 (11)0.0652 (15)0.0572 (14)0.0017 (9)0.0215 (10)0.0081 (10)
C9A0.0387 (12)0.0652 (16)0.0454 (14)0.0005 (11)0.0096 (11)0.0041 (11)
C110.0459 (13)0.0636 (16)0.0375 (13)0.0059 (11)0.0092 (11)0.0033 (10)
C120.0479 (14)0.0695 (17)0.0474 (15)0.0046 (12)0.0018 (12)0.0013 (12)
C130.0591 (15)0.0797 (19)0.0533 (16)0.0077 (14)0.0096 (13)0.0090 (14)
C140.0745 (18)0.0666 (17)0.0545 (17)0.0008 (14)0.0254 (15)0.0084 (13)
C150.0778 (19)0.0675 (19)0.0585 (18)0.0220 (15)0.0185 (15)0.0045 (13)
C160.0521 (14)0.0764 (19)0.0541 (16)0.0140 (13)0.0104 (13)0.0009 (13)
C170.134 (3)0.071 (2)0.103 (3)0.007 (2)0.054 (2)0.0134 (17)
Geometric parameters (Å, º) top
N1—C9A1.352 (3)C8—C8A1.394 (3)
N1—N21.390 (3)C8—H80.9300
N1—C111.411 (3)C8A—N91.403 (3)
N2—C31.321 (3)N9—C9A1.386 (3)
C3—C3A1.395 (3)N9—H90.89 (2)
C3—H30.9300C11—C121.382 (3)
C3A—C9A1.363 (3)C11—C161.383 (3)
C3A—C41.482 (3)C12—C131.375 (3)
C4—C4A1.518 (4)C12—H120.9300
C4—H410.9700C13—C141.377 (4)
C4—H420.9700C13—H130.9300
C4A—C51.377 (4)C14—C151.387 (4)
C4A—C8A1.393 (3)C14—C171.510 (4)
C5—C61.375 (4)C15—C161.374 (3)
C5—H50.9300C15—H150.9300
C6—C71.378 (4)C16—H160.9300
C6—H60.9300C17—H17A0.9600
C7—C81.372 (3)C17—H17B0.9600
C7—H70.9300C17—H17C0.9600
C9A—N1—N2110.29 (19)C4A—C8A—N9122.0 (2)
C9A—N1—C11130.3 (2)C8—C8A—N9118.3 (2)
N2—N1—C11119.4 (2)C9A—N9—C8A116.8 (2)
C3—N2—N1103.7 (2)C9A—N9—H9121.1 (16)
N2—C3—C3A113.5 (2)C8A—N9—H9114.9 (16)
N2—C3—H3123.3N1—C9A—C3A108.7 (2)
C3A—C3—H3123.3N1—C9A—N9126.7 (2)
C9A—C3A—C3103.8 (2)C3A—C9A—N9124.6 (2)
C9A—C3A—C4122.5 (2)C12—C11—C16119.2 (2)
C3—C3A—C4133.6 (2)C12—C11—N1120.8 (2)
C3A—C4—C4A110.5 (2)C16—C11—N1120.0 (2)
C3A—C4—H41109.5C13—C12—C11119.8 (2)
C4A—C4—H41109.5C13—C12—H12120.1
C3A—C4—H42109.5C11—C12—H12120.1
C4A—C4—H42109.5C12—C13—C14122.1 (2)
H41—C4—H42108.1C12—C13—H13119.0
C5—C4A—C8A118.4 (3)C14—C13—H13119.0
C5—C4A—C4119.3 (2)C13—C14—C15117.2 (2)
C8A—C4A—C4122.3 (2)C13—C14—C17121.8 (3)
C6—C5—C4A122.4 (3)C15—C14—C17121.0 (3)
C6—C5—H5118.8C16—C15—C14121.8 (2)
C4A—C5—H5118.8C16—C15—H15119.1
C5—C6—C7118.6 (3)C14—C15—H15119.1
C5—C6—H6120.7C15—C16—C11119.9 (2)
C7—C6—H6120.7C15—C16—H16120.1
C8—C7—C6120.9 (3)C11—C16—H16120.1
C8—C7—H7119.6C14—C17—H17A109.5
C6—C7—H7119.6C14—C17—H17B109.5
C7—C8—C8A120.0 (2)H17A—C17—H17B109.5
C7—C8—H8120.0C14—C17—H17C109.5
C8A—C8—H8120.0H17A—C17—H17C109.5
C4A—C8A—C8119.7 (2)H17B—C17—H17C109.5
C9A—N1—N2—C30.8 (2)C11—N1—C9A—C3A177.1 (2)
C11—N1—N2—C3177.99 (19)N2—N1—C9A—N9179.0 (2)
N1—N2—C3—C3A0.2 (3)C11—N1—C9A—N92.3 (4)
N2—C3—C3A—C9A1.1 (3)C3—C3A—C9A—N11.5 (3)
N2—C3—C3A—C4176.8 (3)C4—C3A—C9A—N1176.7 (2)
C9A—C3A—C4—C4A10.7 (3)C3—C3A—C9A—N9179.0 (2)
C3—C3A—C4—C4A171.7 (3)C4—C3A—C9A—N92.8 (4)
C3A—C4—C4A—C5172.3 (2)C8A—N9—C9A—N1173.8 (2)
C3A—C4—C4A—C8A10.2 (3)C8A—N9—C9A—C3A6.8 (3)
C8A—C4A—C5—C61.8 (4)C9A—N1—C11—C1246.2 (3)
C4—C4A—C5—C6179.4 (3)N2—N1—C11—C12132.4 (2)
C4A—C5—C6—C71.5 (5)C9A—N1—C11—C16135.9 (2)
C5—C6—C7—C80.5 (5)N2—N1—C11—C1645.6 (3)
C6—C7—C8—C8A0.0 (4)C16—C11—C12—C131.5 (4)
C5—C4A—C8A—C81.2 (3)N1—C11—C12—C13176.5 (2)
C4—C4A—C8A—C8178.8 (2)C11—C12—C13—C140.6 (4)
C5—C4A—C8A—N9179.3 (2)C12—C13—C14—C152.2 (4)
C4—C4A—C8A—N91.8 (3)C12—C13—C14—C17176.9 (2)
C7—C8—C8A—C4A0.3 (3)C13—C14—C15—C161.6 (4)
C7—C8—C8A—N9179.8 (2)C17—C14—C15—C16177.4 (3)
C4A—C8A—N9—C9A7.1 (3)C14—C15—C16—C110.4 (4)
C8—C8A—N9—C9A172.3 (2)C12—C11—C16—C152.0 (4)
N2—N1—C9A—C3A1.5 (3)N1—C11—C16—C15176.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N9—H9···N2i0.89 (2)2.50 (2)3.350 (3)161 (2)
C3—H3···Cg2ii0.932.713.423 (3)134
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2.
(III) 1-Phenyl-1H-pyrazolo[3,4-b]quinoline top
Crystal data top
C16H11N3Dx = 1.363 Mg m3
Mr = 245.28Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 8212 reflections
a = 25.145 (2) Åθ = 1.5–27.5°
b = 16.9623 (19) ŵ = 0.08 mm1
c = 16.8138 (19) ÅT = 300 K
V = 7171.4 (13) Å3Plate, colourless
Z = 240.32 × 0.26 × 0.09 mm
F(000) = 3072
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer
5998 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.057
φ and ω scansθmax = 27.5°, θmin = 0.8°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
h = 3232
Tmin = 0.990, Tmax = 0.992k = 2121
166448 measured reflectionsl = 2121
8517 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0398P)2 + 2.3824P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
8517 reflectionsΔρmax = 0.17 e Å3
515 parametersΔρmin = 0.20 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.34470 (5)0.64947 (8)0.43734 (8)0.0359 (3)
N120.28988 (6)0.65129 (9)0.43153 (9)0.0458 (4)
C130.27151 (7)0.59857 (11)0.48108 (11)0.0471 (4)
H130.23550.58840.48850.056*
C13A0.31285 (7)0.55862 (10)0.52232 (10)0.0394 (4)
C140.31723 (7)0.49941 (11)0.57766 (11)0.0452 (4)
H140.28720.47480.59840.054*
C14A0.36838 (7)0.47722 (10)0.60192 (10)0.0397 (4)
C150.37755 (9)0.41692 (11)0.65910 (11)0.0511 (5)
H150.34870.39030.68090.061*
C160.42724 (9)0.39751 (11)0.68240 (11)0.0541 (5)
H160.43240.35760.71950.065*
C170.47127 (8)0.43773 (11)0.65045 (11)0.0489 (5)
H170.50540.42450.66720.059*
C180.46469 (7)0.49572 (11)0.59527 (10)0.0408 (4)
H180.49430.52150.57480.049*
C18A0.41325 (7)0.51725 (9)0.56880 (9)0.0353 (4)
N190.40943 (5)0.57565 (8)0.51317 (8)0.0351 (3)
C19A0.36027 (6)0.59342 (9)0.49250 (9)0.0333 (4)
C1110.37504 (6)0.70029 (9)0.38820 (9)0.0335 (4)
C1120.42985 (7)0.70303 (10)0.39475 (10)0.0395 (4)
H1120.44730.67050.43080.047*
C1130.45848 (7)0.75451 (11)0.34729 (11)0.0465 (4)
H1130.49530.75640.35180.056*
C1140.43322 (8)0.80293 (11)0.29358 (11)0.0477 (4)
H1140.45270.83760.26220.057*
C1150.37871 (8)0.79924 (11)0.28703 (11)0.0501 (5)
H1150.36140.83150.25050.060*
C1160.34925 (7)0.74860 (10)0.33354 (11)0.0447 (4)
H1160.31240.74670.32850.054*
N210.35376 (5)0.05924 (8)0.22135 (8)0.0382 (3)
N220.29872 (6)0.05813 (9)0.21878 (9)0.0457 (4)
C230.28203 (7)0.11046 (11)0.27028 (10)0.0445 (4)
H230.24640.12120.28010.053*
C23A0.32494 (6)0.14900 (10)0.30952 (10)0.0364 (4)
C240.33145 (7)0.20544 (10)0.36768 (10)0.0392 (4)
H240.30230.22910.39180.047*
C24A0.38342 (7)0.22603 (10)0.38931 (10)0.0376 (4)
C250.39481 (8)0.28359 (11)0.44875 (11)0.0477 (5)
H250.36690.30800.47550.057*
C260.44558 (9)0.30327 (12)0.46675 (11)0.0544 (5)
H260.45230.34080.50580.065*
C270.48834 (8)0.26718 (12)0.42656 (11)0.0532 (5)
H270.52300.28200.43860.064*
C280.47958 (7)0.21108 (11)0.37047 (11)0.0469 (4)
H280.50830.18730.34520.056*
C28A0.42711 (7)0.18836 (10)0.34998 (9)0.0369 (4)
N290.42095 (5)0.13183 (8)0.29293 (8)0.0383 (3)
C29A0.37119 (6)0.11471 (9)0.27579 (9)0.0336 (4)
C2110.38268 (7)0.00658 (10)0.17211 (10)0.0386 (4)
C2120.43768 (8)0.00517 (12)0.17404 (12)0.0516 (5)
H2120.45630.03830.20820.062*
C2130.46470 (9)0.04633 (13)0.12442 (14)0.0643 (6)
H2130.50170.04740.12550.077*
C2140.43791 (10)0.09580 (13)0.07369 (13)0.0646 (6)
H2140.45650.13000.04060.078*
C2150.38333 (10)0.09404 (12)0.07255 (12)0.0598 (6)
H2150.36500.12760.03850.072*
C2160.35531 (8)0.04345 (11)0.12107 (11)0.0489 (5)
H2160.31830.04280.11970.059*
N310.28737 (6)0.79630 (9)0.57228 (9)0.0442 (4)
N320.23268 (6)0.79811 (10)0.56896 (11)0.0558 (4)
C330.21501 (8)0.74656 (12)0.62059 (13)0.0565 (5)
H330.17920.73660.62980.068*
C33A0.25736 (7)0.70760 (11)0.66101 (11)0.0459 (4)
C340.26314 (8)0.65060 (11)0.71821 (12)0.0501 (5)
H340.23360.62660.74100.060*
C34A0.31461 (7)0.62948 (10)0.74131 (11)0.0446 (4)
C350.32516 (9)0.57098 (12)0.80038 (12)0.0567 (5)
H350.29690.54530.82500.068*
C360.37552 (9)0.55248 (13)0.82104 (12)0.0615 (6)
H360.38170.51430.85960.074*
C370.41865 (8)0.59056 (12)0.78461 (11)0.0536 (5)
H370.45310.57730.79950.064*
C380.41083 (7)0.64633 (11)0.72811 (11)0.0455 (4)
H380.44000.67090.70480.055*
C38A0.35892 (7)0.66766 (10)0.70424 (10)0.0385 (4)
N390.35367 (6)0.72454 (8)0.64686 (8)0.0392 (3)
C39A0.30417 (7)0.74181 (10)0.62778 (10)0.0385 (4)
C3110.31690 (7)0.84788 (10)0.52224 (10)0.0422 (4)
C3120.37146 (8)0.85344 (11)0.52897 (11)0.0473 (4)
H3120.38950.82300.56630.057*
C3130.39928 (9)0.90427 (12)0.48017 (12)0.0540 (5)
H3130.43610.90780.48480.065*
C3140.37313 (10)0.94998 (13)0.42443 (12)0.0622 (6)
H3140.39200.98420.39170.075*
C3150.31879 (10)0.94404 (13)0.41812 (13)0.0645 (6)
H3150.30090.97470.38080.077*
C3160.29015 (9)0.89327 (12)0.46623 (12)0.0555 (5)
H3160.25340.88950.46120.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0276 (7)0.0431 (8)0.0371 (7)0.0014 (6)0.0055 (6)0.0013 (6)
N120.0292 (8)0.0571 (10)0.0510 (9)0.0010 (7)0.0080 (7)0.0027 (8)
C130.0298 (9)0.0594 (12)0.0519 (11)0.0049 (8)0.0036 (8)0.0020 (9)
C13A0.0329 (9)0.0459 (10)0.0393 (9)0.0040 (7)0.0021 (7)0.0044 (8)
C140.0439 (11)0.0477 (10)0.0441 (10)0.0109 (8)0.0016 (8)0.0005 (8)
C14A0.0463 (10)0.0384 (9)0.0345 (9)0.0028 (7)0.0027 (7)0.0038 (7)
C150.0663 (14)0.0442 (10)0.0427 (10)0.0083 (9)0.0017 (9)0.0040 (8)
C160.0777 (15)0.0424 (10)0.0421 (10)0.0052 (10)0.0095 (10)0.0053 (9)
C170.0591 (12)0.0482 (10)0.0395 (9)0.0165 (9)0.0114 (9)0.0052 (8)
C180.0424 (10)0.0460 (10)0.0341 (9)0.0077 (8)0.0044 (7)0.0046 (7)
C18A0.0424 (10)0.0354 (8)0.0282 (8)0.0038 (7)0.0034 (7)0.0076 (7)
N190.0333 (8)0.0399 (7)0.0321 (7)0.0035 (6)0.0034 (6)0.0019 (6)
C19A0.0347 (9)0.0361 (9)0.0291 (8)0.0001 (7)0.0036 (7)0.0055 (6)
C1110.0370 (9)0.0346 (8)0.0289 (8)0.0006 (7)0.0019 (7)0.0041 (6)
C1120.0361 (10)0.0455 (10)0.0371 (9)0.0035 (7)0.0035 (7)0.0000 (7)
C1130.0366 (10)0.0512 (11)0.0517 (11)0.0005 (8)0.0030 (8)0.0001 (9)
C1140.0531 (12)0.0431 (10)0.0467 (10)0.0002 (8)0.0077 (9)0.0028 (8)
C1150.0561 (13)0.0475 (11)0.0469 (11)0.0064 (9)0.0062 (9)0.0090 (9)
C1160.0387 (10)0.0481 (10)0.0473 (10)0.0032 (8)0.0080 (8)0.0041 (8)
N210.0342 (8)0.0427 (8)0.0375 (7)0.0034 (6)0.0001 (6)0.0036 (6)
N220.0360 (8)0.0554 (9)0.0455 (8)0.0062 (7)0.0008 (7)0.0018 (7)
C230.0346 (10)0.0548 (11)0.0441 (10)0.0021 (8)0.0024 (8)0.0010 (9)
C23A0.0345 (9)0.0402 (9)0.0343 (8)0.0016 (7)0.0045 (7)0.0066 (7)
C240.0425 (10)0.0389 (9)0.0362 (9)0.0019 (7)0.0094 (7)0.0028 (7)
C24A0.0454 (10)0.0356 (9)0.0317 (8)0.0033 (7)0.0045 (7)0.0031 (7)
C250.0619 (13)0.0440 (10)0.0372 (9)0.0031 (9)0.0085 (9)0.0036 (8)
C260.0719 (15)0.0511 (11)0.0402 (10)0.0121 (10)0.0025 (10)0.0082 (9)
C270.0544 (12)0.0593 (12)0.0459 (10)0.0149 (10)0.0088 (9)0.0028 (9)
C280.0419 (11)0.0537 (11)0.0451 (10)0.0058 (8)0.0017 (8)0.0041 (9)
C28A0.0407 (10)0.0383 (9)0.0317 (8)0.0037 (7)0.0009 (7)0.0022 (7)
N290.0360 (8)0.0411 (8)0.0379 (7)0.0029 (6)0.0010 (6)0.0022 (6)
C29A0.0368 (9)0.0349 (8)0.0292 (8)0.0032 (7)0.0013 (7)0.0026 (6)
C2110.0476 (11)0.0349 (8)0.0332 (8)0.0000 (7)0.0011 (7)0.0015 (7)
C2120.0467 (12)0.0545 (11)0.0536 (11)0.0066 (9)0.0051 (9)0.0122 (9)
C2130.0548 (13)0.0690 (14)0.0693 (14)0.0175 (11)0.0006 (11)0.0158 (12)
C2140.0816 (17)0.0541 (13)0.0581 (13)0.0156 (11)0.0074 (12)0.0147 (10)
C2150.0777 (16)0.0506 (12)0.0510 (12)0.0053 (11)0.0005 (11)0.0141 (10)
C2160.0554 (12)0.0476 (10)0.0436 (10)0.0075 (9)0.0005 (9)0.0056 (8)
N310.0386 (9)0.0451 (8)0.0489 (9)0.0054 (7)0.0016 (7)0.0012 (7)
N320.0370 (9)0.0591 (10)0.0713 (11)0.0068 (8)0.0037 (8)0.0001 (9)
C330.0376 (11)0.0580 (12)0.0740 (14)0.0010 (9)0.0031 (10)0.0010 (11)
C33A0.0403 (10)0.0445 (10)0.0530 (11)0.0015 (8)0.0050 (8)0.0078 (9)
C340.0445 (11)0.0486 (11)0.0571 (11)0.0059 (9)0.0119 (9)0.0020 (9)
C34A0.0472 (11)0.0419 (10)0.0448 (10)0.0013 (8)0.0066 (8)0.0068 (8)
C350.0671 (14)0.0498 (11)0.0530 (12)0.0027 (10)0.0150 (10)0.0065 (9)
C360.0797 (16)0.0546 (12)0.0501 (12)0.0097 (11)0.0034 (11)0.0119 (10)
C370.0570 (13)0.0583 (12)0.0455 (11)0.0114 (10)0.0029 (9)0.0015 (9)
C380.0444 (11)0.0496 (11)0.0425 (10)0.0030 (8)0.0004 (8)0.0031 (8)
C38A0.0445 (10)0.0369 (9)0.0342 (8)0.0021 (7)0.0035 (7)0.0069 (7)
N390.0381 (8)0.0406 (8)0.0387 (8)0.0024 (6)0.0021 (6)0.0032 (6)
C39A0.0379 (10)0.0379 (9)0.0398 (9)0.0026 (7)0.0018 (7)0.0084 (7)
C3110.0488 (11)0.0392 (9)0.0386 (9)0.0052 (8)0.0039 (8)0.0053 (7)
C3120.0496 (12)0.0471 (10)0.0451 (10)0.0060 (9)0.0004 (8)0.0015 (8)
C3130.0539 (13)0.0542 (12)0.0537 (11)0.0002 (9)0.0087 (9)0.0016 (10)
C3140.0813 (17)0.0548 (12)0.0506 (12)0.0018 (11)0.0133 (11)0.0071 (10)
C3150.0782 (17)0.0614 (13)0.0538 (12)0.0173 (12)0.0017 (11)0.0120 (11)
C3160.0555 (13)0.0579 (12)0.0532 (11)0.0127 (10)0.0029 (10)0.0032 (10)
Geometric parameters (Å, º) top
N11—N121.3823 (19)C27—H270.9300
N11—C19A1.385 (2)C28—C28A1.417 (2)
N11—C1111.417 (2)C28—H280.9300
N12—C131.306 (2)C28A—N291.365 (2)
C13—C13A1.422 (2)N29—C29A1.316 (2)
C13—H130.9300C211—C2121.383 (3)
C13A—C141.373 (3)C211—C2161.389 (2)
C13A—C19A1.422 (2)C212—C2131.386 (3)
C14—C14A1.401 (2)C212—H2120.9300
C14—H140.9300C213—C2141.373 (3)
C14A—C151.422 (2)C213—H2130.9300
C14A—C18A1.430 (2)C214—C2151.373 (3)
C15—C161.350 (3)C214—H2140.9300
C15—H150.9300C215—C2161.378 (3)
C16—C171.407 (3)C215—H2150.9300
C16—H160.9300C216—H2160.9300
C17—C181.362 (2)N31—N321.377 (2)
C17—H170.9300N31—C39A1.380 (2)
C18—C18A1.416 (2)N31—C3111.423 (2)
C18—H180.9300N32—C331.310 (3)
C18A—N191.366 (2)C33—C33A1.426 (3)
N19—C19A1.319 (2)C33—H330.9300
C111—C1121.383 (2)C33A—C341.371 (3)
C111—C1161.392 (2)C33A—C39A1.426 (2)
C112—C1131.385 (2)C34—C34A1.398 (3)
C112—H1120.9300C34—H340.9300
C113—C1141.376 (3)C34A—C351.429 (3)
C113—H1130.9300C34A—C38A1.432 (2)
C114—C1151.377 (3)C35—C361.350 (3)
C114—H1140.9300C35—H350.9300
C115—C1161.378 (3)C36—C371.403 (3)
C115—H1150.9300C36—H360.9300
C116—H1160.9300C37—C381.355 (3)
N21—C29A1.384 (2)C37—H370.9300
N21—N221.385 (2)C38—C38A1.413 (2)
N21—C2111.419 (2)C38—H380.9300
N22—C231.309 (2)C38A—N391.371 (2)
C23—C23A1.424 (2)N39—C39A1.318 (2)
C23—H230.9300C311—C3121.380 (3)
C23A—C241.378 (2)C311—C3161.390 (3)
C23A—C29A1.419 (2)C312—C3131.381 (3)
C24—C24A1.401 (2)C312—H3120.9300
C24—H240.9300C313—C3141.383 (3)
C24A—C251.426 (2)C313—H3130.9300
C24A—C28A1.433 (2)C314—C3151.374 (3)
C25—C261.354 (3)C314—H3140.9300
C25—H250.9300C315—C3161.384 (3)
C26—C271.410 (3)C315—H3150.9300
C26—H260.9300C316—H3160.9300
C27—C281.358 (3)
N12—N11—C19A110.15 (13)C28A—C28—H28119.7
N12—N11—C111118.82 (13)N29—C28A—C28117.88 (16)
C19A—N11—C111131.01 (14)N29—C28A—C24A123.40 (15)
C13—N12—N11106.99 (14)C28—C28A—C24A118.72 (15)
N12—C13—C13A112.27 (16)C29A—N29—C28A114.63 (14)
N12—C13—H13123.9N29—C29A—N21126.57 (15)
C13A—C13—H13123.9N29—C29A—C23A126.96 (15)
C14—C13A—C13137.55 (17)N21—C29A—C23A106.47 (14)
C14—C13A—C19A118.37 (16)C212—C211—C216119.94 (17)
C13—C13A—C19A104.07 (15)C212—C211—N21120.65 (16)
C13A—C14—C14A117.87 (16)C216—C211—N21119.41 (16)
C13A—C14—H14121.1C211—C212—C213119.14 (19)
C14A—C14—H14121.1C211—C212—H212120.4
C14—C14A—C15122.60 (17)C213—C212—H212120.4
C14—C14A—C18A118.91 (15)C214—C213—C212121.2 (2)
C15—C14A—C18A118.48 (17)C214—C213—H213119.4
C16—C15—C14A121.42 (19)C212—C213—H213119.4
C16—C15—H15119.3C215—C214—C213119.07 (19)
C14A—C15—H15119.3C215—C214—H214120.5
C15—C16—C17119.95 (18)C213—C214—H214120.5
C15—C16—H16120.0C214—C215—C216121.1 (2)
C17—C16—H16120.0C214—C215—H215119.5
C18—C17—C16120.96 (18)C216—C215—H215119.5
C18—C17—H17119.5C215—C216—C211119.53 (19)
C16—C17—H17119.5C215—C216—H216120.2
C17—C18—C18A120.76 (18)C211—C216—H216120.2
C17—C18—H18119.6N32—N31—C39A110.38 (15)
C18A—C18—H18119.6N32—N31—C311118.92 (15)
N19—C18A—C18117.81 (15)C39A—N31—C311130.70 (15)
N19—C18A—C14A123.76 (15)C33—N32—N31107.28 (16)
C18—C18A—C14A118.43 (15)N32—C33—C33A111.84 (18)
C19A—N19—C18A114.34 (14)N32—C33—H33124.1
N19—C19A—N11126.75 (15)C33A—C33—H33124.1
N19—C19A—C13A126.73 (15)C34—C33A—C33137.75 (19)
N11—C19A—C13A106.52 (14)C34—C33A—C39A118.31 (17)
C112—C111—C116119.80 (16)C33—C33A—C39A103.95 (17)
C112—C111—N11120.68 (15)C33A—C34—C34A118.27 (17)
C116—C111—N11119.51 (15)C33A—C34—H34120.9
C111—C112—C113119.55 (16)C34A—C34—H34120.9
C111—C112—H112120.2C34—C34A—C35122.89 (18)
C113—C112—H112120.2C34—C34A—C38A118.92 (17)
C114—C113—C112120.98 (17)C35—C34A—C38A118.19 (17)
C114—C113—H113119.5C36—C35—C34A120.96 (19)
C112—C113—H113119.5C36—C35—H35119.5
C113—C114—C115119.00 (18)C34A—C35—H35119.5
C113—C114—H114120.5C35—C36—C37120.37 (19)
C115—C114—H114120.5C35—C36—H36119.8
C114—C115—C116121.22 (17)C37—C36—H36119.8
C114—C115—H115119.4C38—C37—C36121.03 (19)
C116—C115—H115119.4C38—C37—H37119.5
C115—C116—C111119.44 (17)C36—C37—H37119.5
C115—C116—H116120.3C37—C38—C38A120.80 (18)
C111—C116—H116120.3C37—C38—H38119.6
C29A—N21—N22110.27 (13)C38A—C38—H38119.6
C29A—N21—C211130.67 (14)N39—C38A—C38117.99 (16)
N22—N21—C211119.05 (14)N39—C38A—C34A123.35 (16)
C23—N22—N21106.89 (14)C38—C38A—C34A118.65 (16)
N22—C23—C23A112.01 (16)C39A—N39—C38A114.75 (15)
N22—C23—H23124.0N39—C39A—N31127.05 (16)
C23A—C23—H23124.0N39—C39A—C33A126.40 (17)
C24—C23A—C29A118.10 (15)N31—C39A—C33A106.55 (15)
C24—C23A—C23137.54 (16)C312—C311—C316119.93 (18)
C29A—C23A—C23104.35 (15)C312—C311—N31120.82 (16)
C23A—C24—C24A117.92 (15)C316—C311—N31119.25 (17)
C23A—C24—H24121.0C311—C312—C313119.85 (18)
C24A—C24—H24121.0C311—C312—H312120.1
C24—C24A—C25122.68 (16)C313—C312—H312120.1
C24—C24A—C28A118.98 (15)C312—C313—C314120.8 (2)
C25—C24A—C28A118.34 (16)C312—C313—H313119.6
C26—C25—C24A120.99 (18)C314—C313—H313119.6
C26—C25—H25119.5C315—C314—C313119.0 (2)
C24A—C25—H25119.5C315—C314—H314120.5
C25—C26—C27120.33 (18)C313—C314—H314120.5
C25—C26—H26119.8C314—C315—C316121.2 (2)
C27—C26—H26119.8C314—C315—H315119.4
C28—C27—C26120.91 (18)C316—C315—H315119.4
C28—C27—H27119.5C315—C316—C311119.3 (2)
C26—C27—H27119.5C315—C316—H316120.4
C27—C28—C28A120.69 (18)C311—C316—H316120.4
C27—C28—H28119.7
C19A—N11—N12—C130.05 (19)C28A—N29—C29A—N21179.08 (15)
C111—N11—N12—C13178.71 (15)C28A—N29—C29A—C23A0.6 (2)
N11—N12—C13—C13A0.2 (2)N22—N21—C29A—N29179.43 (15)
N12—C13—C13A—C14178.5 (2)C211—N21—C29A—N291.4 (3)
N12—C13—C13A—C19A0.3 (2)N22—N21—C29A—C23A0.82 (18)
C13—C13A—C14—C14A179.1 (2)C211—N21—C29A—C23A178.39 (16)
C19A—C13A—C14—C14A0.5 (2)C24—C23A—C29A—N291.3 (2)
C13A—C14—C14A—C15179.71 (16)C23—C23A—C29A—N29179.52 (16)
C13A—C14—C14A—C18A0.5 (2)C24—C23A—C29A—N21178.44 (14)
C14—C14A—C15—C16178.94 (18)C23—C23A—C29A—N210.72 (17)
C18A—C14A—C15—C160.3 (3)C29A—N21—C211—C2120.2 (3)
C14A—C15—C16—C170.5 (3)N22—N21—C211—C212178.96 (16)
C15—C16—C17—C180.8 (3)C29A—N21—C211—C216179.25 (16)
C16—C17—C18—C18A0.2 (3)N22—N21—C211—C2161.6 (2)
C17—C18—C18A—N19179.76 (15)C216—C211—C212—C2130.2 (3)
C17—C18—C18A—C14A0.6 (2)N21—C211—C212—C213179.19 (18)
C14—C14A—C18A—N191.2 (2)C211—C212—C213—C2140.1 (3)
C15—C14A—C18A—N19179.55 (15)C212—C213—C214—C2150.1 (4)
C14—C14A—C18A—C18178.40 (15)C213—C214—C215—C2160.2 (3)
C15—C14A—C18A—C180.8 (2)C214—C215—C216—C2110.1 (3)
C18—C18A—N19—C19A178.84 (14)C212—C211—C216—C2150.2 (3)
C14A—C18A—N19—C19A0.8 (2)N21—C211—C216—C215179.29 (17)
C18A—N19—C19A—N11179.46 (14)C39A—N31—N32—C330.0 (2)
C18A—N19—C19A—C13A0.3 (2)C311—N31—N32—C33179.29 (16)
N12—N11—C19A—N19179.94 (15)N31—N32—C33—C33A0.1 (2)
C111—N11—C19A—N191.5 (3)N32—C33—C33A—C34179.6 (2)
N12—N11—C19A—C13A0.11 (18)N32—C33—C33A—C39A0.1 (2)
C111—N11—C19A—C13A178.33 (15)C33—C33A—C34—C34A179.9 (2)
C14—C13A—C19A—N191.0 (3)C39A—C33A—C34—C34A0.5 (3)
C13—C13A—C19A—N19179.95 (16)C33A—C34—C34A—C35179.89 (18)
C14—C13A—C19A—N11178.85 (15)C33A—C34—C34A—C38A0.3 (3)
C13—C13A—C19A—N110.22 (17)C34—C34A—C35—C36179.87 (19)
N12—N11—C111—C112176.94 (15)C38A—C34A—C35—C360.4 (3)
C19A—N11—C111—C1124.7 (3)C34A—C35—C36—C370.0 (3)
N12—N11—C111—C1162.2 (2)C35—C36—C37—C380.1 (3)
C19A—N11—C111—C116176.08 (16)C36—C37—C38—C38A0.1 (3)
C116—C111—C112—C1130.7 (2)C37—C38—C38A—N39179.94 (17)
N11—C111—C112—C113178.53 (15)C37—C38—C38A—C34A0.4 (3)
C111—C112—C113—C1140.1 (3)C34—C34A—C38A—N390.2 (3)
C112—C113—C114—C1150.5 (3)C35—C34A—C38A—N39179.94 (16)
C113—C114—C115—C1160.5 (3)C34—C34A—C38A—C38179.71 (17)
C114—C115—C116—C1110.0 (3)C35—C34A—C38A—C380.5 (2)
C112—C111—C116—C1150.6 (3)C38—C38A—N39—C39A179.66 (15)
N11—C111—C116—C115178.58 (16)C34A—C38A—N39—C39A0.1 (2)
C29A—N21—N22—C230.57 (19)C38A—N39—C39A—N31179.93 (15)
C211—N21—N22—C23178.75 (15)C38A—N39—C39A—C33A0.3 (2)
N21—N22—C23—C23A0.1 (2)N32—N31—C39A—N39179.82 (16)
N22—C23—C23A—C24178.50 (19)C311—N31—C39A—N390.6 (3)
N22—C23—C23A—C29A0.40 (19)N32—N31—C39A—C33A0.03 (19)
C29A—C23A—C24—C24A0.6 (2)C311—N31—C39A—C33A179.23 (17)
C23—C23A—C24—C24A179.44 (19)C34—C33A—C39A—N390.4 (3)
C23A—C24—C24A—C25179.96 (16)C33—C33A—C39A—N39179.79 (17)
C23A—C24—C24A—C28A0.5 (2)C34—C33A—C39A—N31179.70 (16)
C24—C24A—C25—C26178.45 (17)C33—C33A—C39A—N310.06 (19)
C28A—C24A—C25—C261.1 (3)N32—N31—C311—C312173.78 (17)
C24A—C25—C26—C270.3 (3)C39A—N31—C311—C3125.4 (3)
C25—C26—C27—C281.4 (3)N32—N31—C311—C3166.0 (2)
C26—C27—C28—C28A1.1 (3)C39A—N31—C311—C316174.88 (18)
C27—C28—C28A—N29179.77 (17)C316—C311—C312—C3130.2 (3)
C27—C28—C28A—C24A0.3 (3)N31—C311—C312—C313179.56 (17)
C24—C24A—C28A—N291.2 (2)C311—C312—C313—C3140.1 (3)
C25—C24A—C28A—N29179.20 (15)C312—C313—C314—C3150.1 (3)
C24—C24A—C28A—C28178.19 (16)C313—C314—C315—C3160.1 (3)
C25—C24A—C28A—C281.4 (2)C314—C315—C316—C3110.4 (3)
C28—C28A—N29—C29A178.76 (15)C312—C311—C316—C3150.4 (3)
C24A—C28A—N29—C29A0.7 (2)N31—C311—C316—C315179.34 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···Cg3i0.932.843.716 (2)157
C26—H26···Cg40.932.943.795 (2)154
Symmetry code: (i) x, y+1, z+1/2.
(IV) 6-Methyl-1-phenyl-1H-pyrazolo[3,4-b]quinoline top
Crystal data top
C17H13N3Dx = 1.354 Mg m3
Mr = 259.30Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3:HCell parameters from 3437 reflections
a = 29.9202 (12) Åθ = 2.4–30.3°
c = 7.3811 (3) ŵ = 0.08 mm1
V = 5722.4 (5) Å3T = 296 K
Z = 18Block, colourless
F(000) = 24480.42 × 0.26 × 0.14 mm
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer
2077 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.097
φ and ω scansθmax = 27.6°, θmin = 2.7°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
h = 3836
Tmin = 0.978, Tmax = 0.988k = 3838
17651 measured reflectionsl = 99
2942 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056 w = 1/[σ2(Fo2) + (0.0742P)2 + 4.6125P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.173(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.22 e Å3
2942 reflectionsΔρmin = 0.20 e Å3
183 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0006 (2)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.43257 (6)0.28207 (6)0.4528 (2)0.0390 (4)
N20.41980 (7)0.31916 (6)0.4071 (2)0.0466 (5)
C30.37090 (8)0.29442 (8)0.3617 (3)0.0461 (5)
H30.35270.31060.32490.055*
C3A0.34878 (7)0.23988 (7)0.3750 (3)0.0388 (5)
C40.30184 (7)0.19673 (8)0.3434 (3)0.0402 (5)
H40.27410.19950.30040.048*
C4A0.29689 (7)0.14837 (7)0.3780 (2)0.0359 (4)
C50.24970 (7)0.10132 (8)0.3539 (3)0.0405 (5)
H50.22110.10260.31130.049*
C60.24463 (7)0.05443 (7)0.3907 (3)0.0406 (5)
C70.28895 (8)0.05326 (8)0.4524 (3)0.0426 (5)
H70.28620.02150.47750.051*
C80.33536 (7)0.09705 (7)0.4759 (3)0.0408 (5)
H80.36360.09460.51570.049*
C8A0.34122 (7)0.14632 (7)0.4404 (2)0.0349 (4)
N90.38851 (6)0.18886 (6)0.4680 (2)0.0360 (4)
C9A0.39014 (7)0.23301 (7)0.4355 (2)0.0354 (4)
C110.48437 (7)0.29814 (7)0.4980 (2)0.0365 (4)
C120.49663 (8)0.26581 (7)0.5928 (3)0.0414 (5)
H120.47080.23300.62700.050*
C130.54775 (8)0.28264 (8)0.6365 (3)0.0500 (5)
H130.55610.26100.70030.060*
C140.58628 (8)0.33119 (8)0.5863 (3)0.0530 (6)
H140.62040.34220.61640.064*
C150.57403 (8)0.36335 (8)0.4912 (3)0.0497 (5)
H150.60010.39600.45710.060*
C160.52344 (8)0.34733 (7)0.4462 (3)0.0431 (5)
H160.51540.36910.38190.052*
C610.19410 (8)0.00502 (8)0.3690 (3)0.0502 (5)
H61A0.18210.01080.48550.075*
H61B0.19880.01800.29150.075*
H61C0.16910.01230.31630.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0381 (9)0.0310 (8)0.0484 (9)0.0176 (7)0.0021 (7)0.0026 (7)
N20.0501 (11)0.0357 (9)0.0588 (11)0.0250 (8)0.0030 (8)0.0037 (8)
C30.0459 (12)0.0415 (11)0.0594 (13)0.0283 (10)0.0041 (9)0.0072 (9)
C3A0.0409 (11)0.0376 (10)0.0421 (10)0.0228 (9)0.0052 (8)0.0031 (8)
C40.0367 (10)0.0474 (11)0.0430 (11)0.0259 (9)0.0017 (8)0.0033 (8)
C4A0.0335 (9)0.0401 (10)0.0345 (9)0.0188 (8)0.0022 (7)0.0004 (8)
C50.0324 (10)0.0462 (11)0.0417 (11)0.0187 (9)0.0013 (8)0.0007 (8)
C60.0364 (10)0.0403 (11)0.0398 (10)0.0151 (8)0.0028 (8)0.0036 (8)
C70.0414 (11)0.0342 (10)0.0493 (11)0.0168 (9)0.0001 (9)0.0008 (8)
C80.0365 (10)0.0372 (10)0.0502 (11)0.0197 (8)0.0018 (8)0.0005 (8)
C8A0.0342 (10)0.0364 (10)0.0344 (9)0.0178 (8)0.0017 (7)0.0011 (7)
N90.0343 (8)0.0315 (8)0.0415 (9)0.0159 (7)0.0004 (6)0.0009 (6)
C9A0.0359 (10)0.0344 (10)0.0361 (9)0.0178 (8)0.0034 (7)0.0002 (7)
C110.0373 (10)0.0348 (10)0.0360 (10)0.0169 (8)0.0020 (7)0.0047 (7)
C120.0403 (11)0.0327 (10)0.0475 (11)0.0155 (8)0.0010 (8)0.0017 (8)
C130.0492 (13)0.0412 (11)0.0589 (13)0.0220 (10)0.0101 (10)0.0035 (9)
C140.0396 (11)0.0460 (12)0.0666 (14)0.0163 (10)0.0082 (10)0.0098 (10)
C150.0417 (11)0.0376 (11)0.0565 (13)0.0099 (9)0.0026 (9)0.0012 (9)
C160.0452 (11)0.0350 (10)0.0454 (11)0.0173 (9)0.0017 (9)0.0009 (8)
C610.0384 (11)0.0445 (12)0.0576 (13)0.0132 (9)0.0012 (9)0.0075 (10)
Geometric parameters (Å, º) top
N1—N21.384 (2)C8—C8A1.419 (3)
N1—C9A1.385 (2)C8—H80.9300
N1—C111.414 (2)C8A—N91.365 (2)
N2—C31.311 (3)N9—C9A1.320 (2)
C3—C3A1.425 (3)C11—C121.384 (3)
C3—H30.9300C11—C161.399 (3)
C3A—C41.371 (3)C12—C131.388 (3)
C3A—C9A1.424 (3)C12—H120.9300
C4—C4A1.402 (3)C13—C141.379 (3)
C4—H40.9300C13—H130.9300
C4A—C51.421 (3)C14—C151.380 (3)
C4A—C8A1.434 (3)C14—H140.9300
C5—C61.361 (3)C15—C161.381 (3)
C5—H50.9300C15—H150.9300
C6—C71.419 (3)C16—H160.9300
C6—C611.504 (3)C61—H61A0.9600
C7—C81.362 (3)C61—H61B0.9600
C7—H70.9300C61—H61C0.9600
N2—N1—C9A110.67 (15)C8—C8A—C4A117.85 (17)
N2—N1—C11118.68 (15)C9A—N9—C8A114.12 (16)
C9A—N1—C11130.55 (16)N9—C9A—N1126.84 (17)
C3—N2—N1106.70 (16)N9—C9A—C3A127.00 (17)
N2—C3—C3A112.15 (17)N1—C9A—C3A106.16 (16)
N2—C3—H3123.9C12—C11—C16119.97 (18)
C3A—C3—H3123.9C12—C11—N1120.68 (17)
C4—C3A—C9A118.19 (17)C16—C11—N1119.35 (17)
C4—C3A—C3137.48 (19)C11—C12—C13119.53 (18)
C9A—C3A—C3104.32 (17)C11—C12—H12120.2
C3A—C4—C4A118.07 (17)C13—C12—H12120.2
C3A—C4—H4121.0C14—C13—C12120.6 (2)
C4A—C4—H4121.0C14—C13—H13119.7
C4—C4A—C5122.64 (17)C12—C13—H13119.7
C4—C4A—C8A118.68 (17)C13—C14—C15119.8 (2)
C5—C4A—C8A118.69 (17)C13—C14—H14120.1
C6—C5—C4A122.66 (18)C15—C14—H14120.1
C6—C5—H5118.7C14—C15—C16120.50 (19)
C4A—C5—H5118.7C14—C15—H15119.8
C5—C6—C7117.75 (18)C16—C15—H15119.8
C5—C6—C61122.09 (18)C15—C16—C11119.58 (19)
C7—C6—C61120.16 (18)C15—C16—H16120.2
C8—C7—C6122.21 (18)C11—C16—H16120.2
C8—C7—H7118.9C6—C61—H61A109.5
C6—C7—H7118.9C6—C61—H61B109.5
C7—C8—C8A120.84 (18)H61A—C61—H61B109.5
C7—C8—H8119.6C6—C61—H61C109.5
C8A—C8—H8119.6H61A—C61—H61C109.5
N9—C8A—C8118.24 (16)H61B—C61—H61C109.5
N9—C8A—C4A123.91 (16)
C9A—N1—N2—C30.3 (2)C4A—C8A—N9—C9A1.2 (3)
C11—N1—N2—C3176.52 (16)C8A—N9—C9A—N1179.65 (17)
N1—N2—C3—C3A0.1 (2)C8A—N9—C9A—C3A0.6 (3)
N2—C3—C3A—C4178.6 (2)N2—N1—C9A—N9179.91 (17)
N2—C3—C3A—C9A0.1 (2)C11—N1—C9A—N93.8 (3)
C9A—C3A—C4—C4A1.9 (3)N2—N1—C9A—C3A0.3 (2)
C3—C3A—C4—C4A179.5 (2)C11—N1—C9A—C3A175.97 (18)
C3A—C4—C4A—C5178.50 (17)C4—C3A—C9A—N91.0 (3)
C3A—C4—C4A—C8A1.4 (3)C3—C3A—C9A—N9179.99 (18)
C4—C4A—C5—C6178.70 (18)C4—C3A—C9A—N1178.79 (16)
C8A—C4A—C5—C61.2 (3)C3—C3A—C9A—N10.2 (2)
C4A—C5—C6—C71.2 (3)N2—N1—C11—C12161.33 (17)
C4A—C5—C6—C61178.45 (18)C9A—N1—C11—C1222.6 (3)
C5—C6—C7—C80.3 (3)N2—N1—C11—C1618.6 (2)
C61—C6—C7—C8179.29 (19)C9A—N1—C11—C16157.44 (19)
C6—C7—C8—C8A0.5 (3)C16—C11—C12—C130.3 (3)
C7—C8—C8A—N9179.37 (17)N1—C11—C12—C13179.61 (18)
C7—C8—C8A—C4A0.4 (3)C11—C12—C13—C140.0 (3)
C4—C4A—C8A—N90.2 (3)C12—C13—C14—C150.2 (3)
C5—C4A—C8A—N9179.85 (16)C13—C14—C15—C160.1 (3)
C4—C4A—C8A—C8179.55 (17)C14—C15—C16—C110.1 (3)
C5—C4A—C8A—C80.4 (3)C12—C11—C16—C150.4 (3)
C8—C8A—N9—C9A178.58 (16)N1—C11—C16—C15179.55 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···Cg2i0.932.863.585 (2)136
Symmetry code: (i) y+1/3, x+y+2/3, z+2/3.
Selected geometric parameters (Å, °) for compounds (I)–(IV) top
(I)(II)(III)(III)(III)(IV)
(x = nul)(x = 1)(x = 2)(x = 3)(x = nul)
Bond lengths
Nx1—Nx21.390 (3)1.3823 (19)1.385 (2)1.377 (2)1.377 (2)
Nx2—Cx31.321 (3)1.306 (2)1.309 (2)1.312 (3)1.310 (3)
Cx3—Cx3A1.395 (3)1.422 (2)1.424 (2)1.425 (3)1.426 (3)
Cx3A—Cx9A1.363 (3)1.422 (2)1.419 (2)1.428 (3)1.426 (2)
Cx9A—Nx11.352 (3)1.385 (2)1.384 (2)1.378 (2)1.380 (2)
Cx4A—Cx51.377 (4)1.422 (2)1.426 (2)1.430 (3)1.429 (3)
Cx5—Cx61.375 (4)1.350 (3)1.354 (3)1.350 (3)1.350 (3)
Cx6—Cx71.378 (4)1.407 (3)1.410 (3)1.404 (3)1.403 (3)
Cx7—Cx81.372 (3)1.362 (2)1.358 (3)1.354 (3)1.355 (3)
Cx8—Cx8A1.394 (3)1.416 (2)1.417 (2)1.413 (3)1.413 (2)
Cx8A—Cx4A1.393 (3)1.430 (3)1.433 (2)1.431 (3)1.432 (2)
Torsion angles
C12—C13—C19—N1-161.31 (17)
C13—C19—N1—N2-178.42 (16)
C19—N1—N2—C21-174.32 (18)
N1—N2—C21—C22179.67 (17)
Nx2—Nx1—Cx11—Cx12132.4 (2)176.94 (15)-178.96 (16)173.78 (17)161.33 (17)
Hydrogen bonds (Å, °) for compounds (I)–(IV) top
CompoundD—H···AD—HH···AD···AD—H···A
(I)N2—H2···N11i0.92 (3)2.31 (2)3.219 (3)175 (2)
C16—H16···Cg1ii0.932.883.596 (3)133
(II)N9—H9···N2iii0.89 (2)2.50 (2)2.350 (3)161 (2)
C3—H3···Cg2iv0.932.713.423 (3)134
(III)C16—H16···Cg3v0.932.843.716 (2)157
C26—H26···Cg40.932.943.795 (2)154
(IV)C15—H15···Cg2vi0.932.863.585 (2)136
Cg1–Cg4 represent the centroids of the rings C21–C26, C11–C16,C111–C116 and C14A/C15–C18/C18A, respectively

Symmetry codes: (i) -x+1, y+1/2, -z+1/2; (ii) x, -y+1/2, z-1/2; (iii) x-1/2, -y+1/2, z+1/2; (iv) x+1/2, -y+1/2, z-1/2; (v) x, -y+1, z+1/2; (vi) y+1/3, -x+y+2/3, -z+2/3.
 

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