Reactions between aryl­hydrazinium chlorides and 2-chloro­quinoline-3-carbaldehydes: mol­ecular and supra­molecular structures of a hydrazone, a 4,9-di­hydro-1H-pyrazolo­[3,4-b]quinoline and two 1H-pyrazolo­[3,4-b]quinolines

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. 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 (S₆) symmetry, which are themselves linked into a three-dimensional array by π–π stacking inter­actions.

Computing details

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

Crystal data

C17H14ClN3	Dx = 1.305 Mg m^−3
Mr = 295.76	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3572 reflections
a = 14.730 (6) Å	θ = 2.5–28.0°
b = 12.413 (5) Å	µ = 0.25 mm^−1
c = 16.464 (5) Å	T = 296 K
V = 3010 (2) Å^3	Block, colourless
Z = 8	0.28 × 0.22 × 0.14 mm
F(000) = 1232

Data collection

Agilent Xcalibur Eos Gemini diffractometer	2200 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	Rint = 0.080
φ and ω scans	θmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −19→19
Tmin = 0.901, Tmax = 0.966	k = −16→16
59891 measured reflections	l = −20→21
3467 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 0.5907P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3467 reflections	Δρmax = 0.18 e Å^−3
194 parameters	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.31620 (11)	0.44493 (11)	0.28740 (10)	0.0500 (4)
N2	0.31793 (12)	0.54330 (13)	0.32296 (11)	0.0590 (5)
H2	0.3735 (16)	0.5762 (17)	0.3265 (13)	0.071*
N11	0.48200 (10)	0.14748 (11)	0.17393 (9)	0.0454 (4)
C12	0.47319 (11)	0.23884 (14)	0.21195 (10)	0.0415 (4)
Cl12	0.57326 (3)	0.28779 (4)	0.25668 (4)	0.0642 (2)
C13	0.39251 (12)	0.30123 (13)	0.22095 (11)	0.0409 (4)
C14	0.31606 (11)	0.25532 (15)	0.18813 (11)	0.0467 (4)
H14	0.2608	0.2911	0.1926	0.056*
C14A	0.31925 (12)	0.15503 (14)	0.14768 (11)	0.0439 (4)
C15	0.24215 (14)	0.10411 (17)	0.11263 (13)	0.0597 (5)
H15	0.1852	0.1356	0.1180	0.072*
C16	0.25104 (16)	0.00923 (19)	0.07104 (14)	0.0678 (6)
H16	0.2001	−0.0235	0.0486	0.081*
C17	0.33652 (17)	−0.03884 (17)	0.06209 (14)	0.0690 (6)
H17	0.3419	−0.1025	0.0327	0.083*
C18	0.41181 (15)	0.00635 (16)	0.09589 (12)	0.0594 (5)
H18	0.4680	−0.0269	0.0899	0.071*
C18A	0.40476 (12)	0.10393 (14)	0.14009 (11)	0.0433 (4)
C19	0.39167 (13)	0.40638 (14)	0.26179 (12)	0.0488 (5)
H19	0.4454	0.4446	0.2690	0.059*
C21	0.23925 (14)	0.58540 (14)	0.35853 (11)	0.0490 (5)
C22	0.24187 (15)	0.68640 (14)	0.39531 (12)	0.0545 (5)
H22	0.2953	0.7263	0.3947	0.065*
C23	0.16556 (16)	0.72756 (16)	0.43267 (12)	0.0598 (6)
H23	0.1687	0.7951	0.4569	0.072*
C24	0.08422 (15)	0.67110 (17)	0.43515 (12)	0.0586 (5)
C25	0.08211 (15)	0.57136 (18)	0.39657 (14)	0.0666 (6)
H25	0.0282	0.5324	0.3960	0.080*
C26	0.15815 (14)	0.52843 (17)	0.35900 (13)	0.0618 (6)
H26	0.1548	0.4613	0.3341	0.074*
C27	0.00103 (19)	0.7156 (2)	0.47776 (15)	0.0857 (8)
H27A	−0.0435	0.7361	0.4381	0.128*
H27B	0.0179	0.7775	0.5093	0.128*
H27C	−0.0240	0.6615	0.5129	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0590 (10)	0.0375 (8)	0.0535 (10)	0.0021 (7)	0.0000 (8)	−0.0056 (7)
N2	0.0590 (11)	0.0435 (9)	0.0743 (12)	−0.0056 (8)	0.0049 (9)	−0.0131 (8)
N11	0.0442 (8)	0.0450 (8)	0.0470 (9)	0.0061 (7)	−0.0026 (7)	0.0002 (7)
C12	0.0383 (9)	0.0457 (9)	0.0405 (10)	−0.0012 (8)	−0.0003 (8)	0.0044 (8)
Cl12	0.0432 (3)	0.0641 (3)	0.0854 (4)	−0.0046 (2)	−0.0134 (3)	−0.0079 (3)
C13	0.0401 (9)	0.0402 (9)	0.0424 (10)	−0.0001 (7)	0.0031 (8)	0.0017 (7)
C14	0.0375 (9)	0.0496 (10)	0.0528 (11)	0.0032 (8)	0.0031 (8)	−0.0038 (9)
C14A	0.0436 (10)	0.0459 (9)	0.0421 (10)	−0.0020 (8)	−0.0009 (8)	−0.0004 (8)
C15	0.0478 (11)	0.0647 (13)	0.0666 (14)	−0.0034 (10)	−0.0078 (10)	−0.0095 (11)
C16	0.0715 (14)	0.0648 (13)	0.0670 (14)	−0.0135 (11)	−0.0206 (12)	−0.0095 (11)
C17	0.0873 (17)	0.0510 (12)	0.0687 (15)	0.0074 (11)	−0.0220 (13)	−0.0150 (11)
C18	0.0676 (13)	0.0510 (11)	0.0596 (13)	0.0149 (10)	−0.0103 (10)	−0.0097 (9)
C18A	0.0508 (10)	0.0415 (9)	0.0375 (10)	0.0037 (8)	−0.0033 (8)	0.0032 (7)
C19	0.0484 (10)	0.0401 (9)	0.0577 (12)	−0.0035 (8)	0.0012 (9)	−0.0033 (8)
C21	0.0602 (12)	0.0395 (9)	0.0473 (11)	0.0030 (9)	−0.0037 (9)	−0.0025 (8)
C22	0.0719 (14)	0.0401 (10)	0.0514 (12)	−0.0015 (9)	−0.0058 (11)	−0.0017 (8)
C23	0.0868 (16)	0.0446 (11)	0.0480 (12)	0.0131 (11)	−0.0084 (11)	−0.0062 (9)
C24	0.0683 (14)	0.0605 (12)	0.0469 (12)	0.0191 (11)	−0.0123 (10)	−0.0080 (10)
C25	0.0563 (13)	0.0713 (14)	0.0721 (15)	0.0055 (11)	−0.0098 (11)	−0.0204 (12)
C26	0.0645 (13)	0.0493 (11)	0.0716 (15)	0.0005 (10)	−0.0060 (11)	−0.0208 (11)
C27	0.0830 (17)	0.0969 (18)	0.0771 (16)	0.0300 (14)	−0.0036 (14)	−0.0244 (14)

Geometric parameters (Å, º)

N1—C19	1.282 (2)	C17—H17	0.9300
N1—N2	1.354 (2)	C18—C18A	1.417 (3)
N2—C21	1.400 (3)	C18—H18	0.9300
N2—H2	0.92 (2)	C19—H19	0.9300
N11—C12	1.302 (2)	C21—C26	1.388 (3)
N11—C18A	1.377 (2)	C21—C22	1.393 (3)
C12—C13	1.426 (2)	C22—C23	1.379 (3)
C12—Cl12	1.7562 (18)	C22—H22	0.9300
C13—C14	1.373 (2)	C23—C24	1.389 (3)
C13—C19	1.468 (2)	C23—H23	0.9300
C14—C14A	1.413 (3)	C24—C25	1.392 (3)
C14—H14	0.9300	C24—C27	1.516 (3)
C14A—C18A	1.416 (2)	C25—C26	1.386 (3)
C14A—C15	1.422 (3)	C25—H25	0.9300
C15—C16	1.369 (3)	C26—H26	0.9300
C15—H15	0.9300	C27—H27A	0.9600
C16—C17	1.401 (3)	C27—H27B	0.9600
C16—H16	0.9300	C27—H27C	0.9600
C17—C18	1.362 (3)
C19—N1—N2	117.54 (16)	N11—C18A—C18	118.87 (17)
N1—N2—C21	120.12 (16)	C14A—C18A—C18	119.57 (17)
N1—N2—H2	116.5 (14)	N1—C19—C13	119.33 (17)
C21—N2—H2	123.1 (14)	N1—C19—H19	120.3
C12—N11—C18A	117.00 (15)	C13—C19—H19	120.3
N11—C12—C13	127.30 (16)	C26—C21—C22	118.68 (19)
N11—C12—Cl12	114.79 (13)	C26—C21—N2	121.65 (17)
C13—C12—Cl12	117.90 (14)	C22—C21—N2	119.67 (18)
C14—C13—C12	114.65 (15)	C23—C22—C21	120.3 (2)
C14—C13—C19	122.85 (16)	C23—C22—H22	119.8
C12—C13—C19	122.50 (16)	C21—C22—H22	119.8
C13—C14—C14A	121.61 (16)	C22—C23—C24	121.95 (19)
C13—C14—H14	119.2	C22—C23—H23	119.0
C14A—C14—H14	119.2	C24—C23—H23	119.0
C14—C14A—C18A	117.78 (16)	C23—C24—C25	117.1 (2)
C14—C14A—C15	123.81 (17)	C23—C24—C27	121.8 (2)
C18A—C14A—C15	118.39 (17)	C25—C24—C27	121.1 (2)
C16—C15—C14A	120.6 (2)	C26—C25—C24	121.8 (2)
C16—C15—H15	119.7	C26—C25—H25	119.1
C14A—C15—H15	119.7	C24—C25—H25	119.1
C15—C16—C17	120.3 (2)	C25—C26—C21	120.14 (19)
C15—C16—H16	119.8	C25—C26—H26	119.9
C17—C16—H16	119.8	C21—C26—H26	119.9
C18—C17—C16	120.9 (2)	C24—C27—H27A	109.5
C18—C17—H17	119.6	C24—C27—H27B	109.5
C16—C17—H17	119.6	H27A—C27—H27B	109.5
C17—C18—C18A	120.2 (2)	C24—C27—H27C	109.5
C17—C18—H18	119.9	H27A—C27—H27C	109.5
C18A—C18—H18	119.9	H27B—C27—H27C	109.5
N11—C18A—C14A	121.56 (16)
C19—N1—N2—C21	−174.32 (18)	C14—C14A—C18A—C18	−176.37 (17)
C18A—N11—C12—C13	−1.8 (3)	C15—C14A—C18A—C18	2.1 (3)
C18A—N11—C12—Cl12	177.92 (12)	C17—C18—C18A—N11	179.69 (19)
N11—C12—C13—C14	3.0 (3)	C17—C18—C18A—C14A	−1.1 (3)
Cl12—C12—C13—C14	−176.74 (13)	N2—N1—C19—C13	−178.42 (16)
N11—C12—C13—C19	−176.76 (17)	C14—C13—C19—N1	19.0 (3)
Cl12—C12—C13—C19	3.5 (2)	C12—C13—C19—N1	−161.31 (17)
C12—C13—C14—C14A	−1.1 (3)	N1—N2—C21—C26	0.4 (3)
C19—C13—C14—C14A	178.65 (17)	N1—N2—C21—C22	179.67 (17)
C13—C14—C14A—C18A	−1.6 (3)	C26—C21—C22—C23	1.2 (3)
C13—C14—C14A—C15	−179.96 (18)	N2—C21—C22—C23	−178.11 (18)
C14—C14A—C15—C16	176.95 (19)	C21—C22—C23—C24	0.0 (3)
C18A—C14A—C15—C16	−1.4 (3)	C22—C23—C24—C25	−1.4 (3)
C14A—C15—C16—C17	−0.3 (3)	C22—C23—C24—C27	178.73 (19)
C15—C16—C17—C18	1.4 (4)	C23—C24—C25—C26	1.6 (3)
C16—C17—C18—C18A	−0.7 (3)	C27—C24—C25—C26	−178.5 (2)
C12—N11—C18A—C14A	−1.3 (2)	C24—C25—C26—C21	−0.5 (3)
C12—N11—C18A—C18	177.97 (17)	C22—C21—C26—C25	−0.9 (3)
C14—C14A—C18A—N11	2.9 (3)	N2—C21—C26—C25	178.4 (2)
C15—C14A—C18A—N11	−178.66 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N11^i	0.92 (2)	2.31 (2)	3.219 (3)	175 (2)
C16—H16···Cg1^ii	0.93	2.88	3.596 (3)	133

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z−3/2.

(II) 1-(4-Methylphenyl)-4,9-dihydro-1H-pyrazolo[3,4-b]quinoline

Crystal data

C17H15N3	F(000) = 552
Mr = 261.32	Dx = 1.279 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.6676 (17) Å	Cell parameters from 3036 reflections
b = 26.571 (8) Å	θ = 2.8–27.6°
c = 7.912 (2) Å	µ = 0.08 mm^−1
β = 104.561 (9)°	T = 300 K
V = 1356.7 (6) Å^3	Plate, colourless
Z = 4	0.34 × 0.22 × 0.08 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer	1529 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	Rint = 0.054
φ and ω scans	θmax = 25.6°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −8→7
Tmin = 0.992, Tmax = 0.994	k = −32→32
12345 measured reflections	l = −8→9
2509 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0757P)^2 + 0.1113P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2509 reflections	Δρmax = 0.13 e Å^−3
185 parameters	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.7866 (3)	0.25204 (7)	0.5796 (3)	0.0534 (5)
N2	0.9607 (3)	0.25073 (9)	0.5131 (3)	0.0646 (6)
C3	0.9912 (4)	0.20219 (11)	0.4936 (3)	0.0623 (7)
H3	1.0991	0.1896	0.4509	0.075*
C3A	0.8459 (3)	0.17157 (10)	0.5432 (3)	0.0557 (6)
C4	0.8093 (4)	0.11650 (10)	0.5386 (4)	0.0745 (8)
H41	0.9377	0.0992	0.5925	0.089*
H42	0.7638	0.1054	0.4183	0.089*
C4A	0.6462 (4)	0.10322 (10)	0.6348 (3)	0.0565 (7)
C5	0.6082 (5)	0.05338 (11)	0.6632 (4)	0.0740 (8)
H5	0.6845	0.0288	0.6236	0.089*
C6	0.4615 (6)	0.03868 (12)	0.7481 (4)	0.0903 (10)
H6	0.4410	0.0048	0.7680	0.108*
C7	0.3455 (5)	0.07523 (12)	0.8030 (4)	0.0802 (9)
H7	0.2449	0.0659	0.8597	0.096*
C8	0.3765 (4)	0.12526 (9)	0.7752 (3)	0.0589 (7)
H8	0.2972	0.1495	0.8129	0.071*
C8A	0.5270 (3)	0.13975 (9)	0.6903 (3)	0.0484 (6)
N9	0.5542 (3)	0.19129 (8)	0.6648 (3)	0.0533 (6)
H9	0.509 (4)	0.2115 (9)	0.737 (3)	0.064*
C9A	0.7211 (3)	0.20479 (9)	0.5997 (3)	0.0499 (6)
C11	0.7043 (4)	0.29895 (9)	0.6118 (3)	0.0492 (6)
C12	0.4944 (4)	0.30852 (10)	0.5550 (3)	0.0574 (7)
H12	0.4044	0.2833	0.5003	0.069*
C13	0.4189 (4)	0.35541 (11)	0.5794 (3)	0.0648 (7)
H13	0.2771	0.3613	0.5416	0.078*
C14	0.5467 (4)	0.39397 (10)	0.6581 (3)	0.0636 (7)
C15	0.7561 (4)	0.38321 (10)	0.7179 (4)	0.0677 (8)
H15	0.8456	0.4083	0.7743	0.081*
C16	0.8350 (4)	0.33655 (10)	0.6963 (3)	0.0614 (7)
H16	0.9760	0.3303	0.7384	0.074*
C17	0.4643 (5)	0.44609 (11)	0.6764 (5)	0.0984 (11)
H17A	0.5206	0.4694	0.6078	0.148*
H17B	0.5040	0.4561	0.7968	0.148*
H17C	0.3159	0.4459	0.6363	0.148*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0450 (11)	0.0683 (15)	0.0497 (12)	−0.0035 (10)	0.0169 (10)	−0.0006 (10)
N2	0.0491 (12)	0.0903 (18)	0.0604 (14)	−0.0012 (11)	0.0247 (11)	0.0070 (12)
C3	0.0478 (14)	0.085 (2)	0.0599 (18)	0.0084 (13)	0.0232 (13)	0.0015 (14)
C3A	0.0416 (12)	0.0708 (17)	0.0570 (16)	0.0028 (12)	0.0167 (12)	−0.0024 (12)
C4	0.0566 (16)	0.081 (2)	0.094 (2)	0.0081 (14)	0.0341 (16)	−0.0089 (15)
C4A	0.0557 (15)	0.0601 (16)	0.0516 (15)	0.0039 (12)	0.0092 (12)	−0.0058 (12)
C5	0.082 (2)	0.069 (2)	0.074 (2)	0.0052 (15)	0.0264 (17)	−0.0050 (15)
C6	0.116 (3)	0.064 (2)	0.099 (3)	−0.0045 (18)	0.041 (2)	0.0020 (17)
C7	0.090 (2)	0.079 (2)	0.079 (2)	−0.0178 (17)	0.0355 (18)	−0.0017 (16)
C8	0.0601 (15)	0.0699 (18)	0.0511 (15)	−0.0069 (13)	0.0222 (13)	−0.0092 (12)
C8A	0.0415 (12)	0.0567 (16)	0.0439 (14)	−0.0026 (11)	0.0050 (11)	−0.0042 (11)
N9	0.0424 (11)	0.0652 (15)	0.0572 (14)	−0.0017 (9)	0.0215 (10)	−0.0081 (10)
C9A	0.0387 (12)	0.0652 (16)	0.0454 (14)	−0.0005 (11)	0.0096 (11)	−0.0041 (11)
C11	0.0459 (13)	0.0636 (16)	0.0375 (13)	−0.0059 (11)	0.0092 (11)	0.0033 (10)
C12	0.0479 (14)	0.0695 (17)	0.0474 (15)	−0.0046 (12)	−0.0018 (12)	0.0013 (12)
C13	0.0591 (15)	0.0797 (19)	0.0533 (16)	0.0077 (14)	0.0096 (13)	0.0090 (14)
C14	0.0745 (18)	0.0666 (17)	0.0545 (17)	−0.0008 (14)	0.0254 (15)	0.0084 (13)
C15	0.0778 (19)	0.0675 (19)	0.0585 (18)	−0.0220 (15)	0.0185 (15)	−0.0045 (13)
C16	0.0521 (14)	0.0764 (19)	0.0541 (16)	−0.0140 (13)	0.0104 (13)	0.0009 (13)
C17	0.134 (3)	0.071 (2)	0.103 (3)	0.007 (2)	0.054 (2)	0.0134 (17)

Geometric parameters (Å, º)

N1—C9A	1.352 (3)	C8—C8A	1.394 (3)
N1—N2	1.390 (3)	C8—H8	0.9300
N1—C11	1.411 (3)	C8A—N9	1.403 (3)
N2—C3	1.321 (3)	N9—C9A	1.386 (3)
C3—C3A	1.395 (3)	N9—H9	0.89 (2)
C3—H3	0.9300	C11—C12	1.382 (3)
C3A—C9A	1.363 (3)	C11—C16	1.383 (3)
C3A—C4	1.482 (3)	C12—C13	1.375 (3)
C4—C4A	1.518 (4)	C12—H12	0.9300
C4—H41	0.9700	C13—C14	1.377 (4)
C4—H42	0.9700	C13—H13	0.9300
C4A—C5	1.377 (4)	C14—C15	1.387 (4)
C4A—C8A	1.393 (3)	C14—C17	1.510 (4)
C5—C6	1.375 (4)	C15—C16	1.374 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.378 (4)	C16—H16	0.9300
C6—H6	0.9300	C17—H17A	0.9600
C7—C8	1.372 (3)	C17—H17B	0.9600
C7—H7	0.9300	C17—H17C	0.9600
C9A—N1—N2	110.29 (19)	C4A—C8A—N9	122.0 (2)
C9A—N1—C11	130.3 (2)	C8—C8A—N9	118.3 (2)
N2—N1—C11	119.4 (2)	C9A—N9—C8A	116.8 (2)
C3—N2—N1	103.7 (2)	C9A—N9—H9	121.1 (16)
N2—C3—C3A	113.5 (2)	C8A—N9—H9	114.9 (16)
N2—C3—H3	123.3	N1—C9A—C3A	108.7 (2)
C3A—C3—H3	123.3	N1—C9A—N9	126.7 (2)
C9A—C3A—C3	103.8 (2)	C3A—C9A—N9	124.6 (2)
C9A—C3A—C4	122.5 (2)	C12—C11—C16	119.2 (2)
C3—C3A—C4	133.6 (2)	C12—C11—N1	120.8 (2)
C3A—C4—C4A	110.5 (2)	C16—C11—N1	120.0 (2)
C3A—C4—H41	109.5	C13—C12—C11	119.8 (2)
C4A—C4—H41	109.5	C13—C12—H12	120.1
C3A—C4—H42	109.5	C11—C12—H12	120.1
C4A—C4—H42	109.5	C12—C13—C14	122.1 (2)
H41—C4—H42	108.1	C12—C13—H13	119.0
C5—C4A—C8A	118.4 (3)	C14—C13—H13	119.0
C5—C4A—C4	119.3 (2)	C13—C14—C15	117.2 (2)
C8A—C4A—C4	122.3 (2)	C13—C14—C17	121.8 (3)
C6—C5—C4A	122.4 (3)	C15—C14—C17	121.0 (3)
C6—C5—H5	118.8	C16—C15—C14	121.8 (2)
C4A—C5—H5	118.8	C16—C15—H15	119.1
C5—C6—C7	118.6 (3)	C14—C15—H15	119.1
C5—C6—H6	120.7	C15—C16—C11	119.9 (2)
C7—C6—H6	120.7	C15—C16—H16	120.1
C8—C7—C6	120.9 (3)	C11—C16—H16	120.1
C8—C7—H7	119.6	C14—C17—H17A	109.5
C6—C7—H7	119.6	C14—C17—H17B	109.5
C7—C8—C8A	120.0 (2)	H17A—C17—H17B	109.5
C7—C8—H8	120.0	C14—C17—H17C	109.5
C8A—C8—H8	120.0	H17A—C17—H17C	109.5
C4A—C8A—C8	119.7 (2)	H17B—C17—H17C	109.5
C9A—N1—N2—C3	0.8 (2)	C11—N1—C9A—C3A	177.1 (2)
C11—N1—N2—C3	−177.99 (19)	N2—N1—C9A—N9	179.0 (2)
N1—N2—C3—C3A	0.2 (3)	C11—N1—C9A—N9	−2.3 (4)
N2—C3—C3A—C9A	−1.1 (3)	C3—C3A—C9A—N1	1.5 (3)
N2—C3—C3A—C4	176.8 (3)	C4—C3A—C9A—N1	−176.7 (2)
C9A—C3A—C4—C4A	−10.7 (3)	C3—C3A—C9A—N9	−179.0 (2)
C3—C3A—C4—C4A	171.7 (3)	C4—C3A—C9A—N9	2.8 (4)
C3A—C4—C4A—C5	−172.3 (2)	C8A—N9—C9A—N1	−173.8 (2)
C3A—C4—C4A—C8A	10.2 (3)	C8A—N9—C9A—C3A	6.8 (3)
C8A—C4A—C5—C6	−1.8 (4)	C9A—N1—C11—C12	−46.2 (3)
C4—C4A—C5—C6	−179.4 (3)	N2—N1—C11—C12	132.4 (2)
C4A—C5—C6—C7	1.5 (5)	C9A—N1—C11—C16	135.9 (2)
C5—C6—C7—C8	−0.5 (5)	N2—N1—C11—C16	−45.6 (3)
C6—C7—C8—C8A	0.0 (4)	C16—C11—C12—C13	1.5 (4)
C5—C4A—C8A—C8	1.2 (3)	N1—C11—C12—C13	−176.5 (2)
C4—C4A—C8A—C8	178.8 (2)	C11—C12—C13—C14	0.6 (4)
C5—C4A—C8A—N9	−179.3 (2)	C12—C13—C14—C15	−2.2 (4)
C4—C4A—C8A—N9	−1.8 (3)	C12—C13—C14—C17	176.9 (2)
C7—C8—C8A—C4A	−0.3 (3)	C13—C14—C15—C16	1.6 (4)
C7—C8—C8A—N9	−179.8 (2)	C17—C14—C15—C16	−177.4 (3)
C4A—C8A—N9—C9A	−7.1 (3)	C14—C15—C16—C11	0.4 (4)
C8—C8A—N9—C9A	172.3 (2)	C12—C11—C16—C15	−2.0 (4)
N2—N1—C9A—C3A	−1.5 (3)	N1—C11—C16—C15	176.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···N2^i	0.89 (2)	2.50 (2)	3.350 (3)	161 (2)
C3—H3···Cg2^ii	0.93	2.71	3.423 (3)	134

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2.

(III) 1-Phenyl-1H-pyrazolo[3,4-b]quinoline

Crystal data

C16H11N3	Dx = 1.363 Mg m^−3
Mr = 245.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 8212 reflections
a = 25.145 (2) Å	θ = 1.5–27.5°
b = 16.9623 (19) Å	µ = 0.08 mm^−1
c = 16.8138 (19) Å	T = 300 K
V = 7171.4 (13) Å^3	Plate, colourless
Z = 24	0.32 × 0.26 × 0.09 mm
F(000) = 3072

Data collection

Agilent Xcalibur Eos Gemini diffractometer	5998 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	Rint = 0.057
φ and ω scans	θmax = 27.5°, θmin = 0.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −32→32
Tmin = 0.990, Tmax = 0.992	k = −21→21
166448 measured reflections	l = −21→21
8517 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0398P)^2 + 2.3824P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
8517 reflections	Δρmax = 0.17 e Å^−3
515 parameters	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N11	0.34470 (5)	0.64947 (8)	0.43734 (8)	0.0359 (3)
N12	0.28988 (6)	0.65129 (9)	0.43153 (9)	0.0458 (4)
C13	0.27151 (7)	0.59857 (11)	0.48108 (11)	0.0471 (4)
H13	0.2355	0.5884	0.4885	0.056*
C13A	0.31285 (7)	0.55862 (10)	0.52232 (10)	0.0394 (4)
C14	0.31723 (7)	0.49941 (11)	0.57766 (11)	0.0452 (4)
H14	0.2872	0.4748	0.5984	0.054*
C14A	0.36838 (7)	0.47722 (10)	0.60192 (10)	0.0397 (4)
C15	0.37755 (9)	0.41692 (11)	0.65910 (11)	0.0511 (5)
H15	0.3487	0.3903	0.6809	0.061*
C16	0.42724 (9)	0.39751 (11)	0.68240 (11)	0.0541 (5)
H16	0.4324	0.3576	0.7195	0.065*
C17	0.47127 (8)	0.43773 (11)	0.65045 (11)	0.0489 (5)
H17	0.5054	0.4245	0.6672	0.059*
C18	0.46469 (7)	0.49572 (11)	0.59527 (10)	0.0408 (4)
H18	0.4943	0.5215	0.5748	0.049*
C18A	0.41325 (7)	0.51725 (9)	0.56880 (9)	0.0353 (4)
N19	0.40943 (5)	0.57565 (8)	0.51317 (8)	0.0351 (3)
C19A	0.36027 (6)	0.59342 (9)	0.49250 (9)	0.0333 (4)
C111	0.37504 (6)	0.70029 (9)	0.38820 (9)	0.0335 (4)
C112	0.42985 (7)	0.70303 (10)	0.39475 (10)	0.0395 (4)
H112	0.4473	0.6705	0.4308	0.047*
C113	0.45848 (7)	0.75451 (11)	0.34729 (11)	0.0465 (4)
H113	0.4953	0.7564	0.3518	0.056*
C114	0.43322 (8)	0.80293 (11)	0.29358 (11)	0.0477 (4)
H114	0.4527	0.8376	0.2622	0.057*
C115	0.37871 (8)	0.79924 (11)	0.28703 (11)	0.0501 (5)
H115	0.3614	0.8315	0.2505	0.060*
C116	0.34925 (7)	0.74860 (10)	0.33354 (11)	0.0447 (4)
H116	0.3124	0.7467	0.3285	0.054*
N21	0.35376 (5)	0.05924 (8)	0.22135 (8)	0.0382 (3)
N22	0.29872 (6)	0.05813 (9)	0.21878 (9)	0.0457 (4)
C23	0.28203 (7)	0.11046 (11)	0.27028 (10)	0.0445 (4)
H23	0.2464	0.1212	0.2801	0.053*
C23A	0.32494 (6)	0.14900 (10)	0.30952 (10)	0.0364 (4)
C24	0.33145 (7)	0.20544 (10)	0.36768 (10)	0.0392 (4)
H24	0.3023	0.2291	0.3918	0.047*
C24A	0.38342 (7)	0.22603 (10)	0.38931 (10)	0.0376 (4)
C25	0.39481 (8)	0.28359 (11)	0.44875 (11)	0.0477 (5)
H25	0.3669	0.3080	0.4755	0.057*
C26	0.44558 (9)	0.30327 (12)	0.46675 (11)	0.0544 (5)
H26	0.4523	0.3408	0.5058	0.065*
C27	0.48834 (8)	0.26718 (12)	0.42656 (11)	0.0532 (5)
H27	0.5230	0.2820	0.4386	0.064*
C28	0.47958 (7)	0.21108 (11)	0.37047 (11)	0.0469 (4)
H28	0.5083	0.1873	0.3452	0.056*
C28A	0.42711 (7)	0.18836 (10)	0.34998 (9)	0.0369 (4)
N29	0.42095 (5)	0.13183 (8)	0.29293 (8)	0.0383 (3)
C29A	0.37119 (6)	0.11471 (9)	0.27579 (9)	0.0336 (4)
C211	0.38268 (7)	0.00658 (10)	0.17211 (10)	0.0386 (4)
C212	0.43768 (8)	0.00517 (12)	0.17404 (12)	0.0516 (5)
H212	0.4563	0.0383	0.2082	0.062*
C213	0.46470 (9)	−0.04633 (13)	0.12442 (14)	0.0643 (6)
H213	0.5017	−0.0474	0.1255	0.077*
C214	0.43791 (10)	−0.09580 (13)	0.07369 (13)	0.0646 (6)
H214	0.4565	−0.1300	0.0406	0.078*
C215	0.38333 (10)	−0.09404 (12)	0.07255 (12)	0.0598 (6)
H215	0.3650	−0.1276	0.0385	0.072*
C216	0.35531 (8)	−0.04345 (11)	0.12107 (11)	0.0489 (5)
H216	0.3183	−0.0428	0.1197	0.059*
N31	0.28737 (6)	0.79630 (9)	0.57228 (9)	0.0442 (4)
N32	0.23268 (6)	0.79811 (10)	0.56896 (11)	0.0558 (4)
C33	0.21501 (8)	0.74656 (12)	0.62059 (13)	0.0565 (5)
H33	0.1792	0.7366	0.6298	0.068*
C33A	0.25736 (7)	0.70760 (11)	0.66101 (11)	0.0459 (4)
C34	0.26314 (8)	0.65060 (11)	0.71821 (12)	0.0501 (5)
H34	0.2336	0.6266	0.7410	0.060*
C34A	0.31461 (7)	0.62948 (10)	0.74131 (11)	0.0446 (4)
C35	0.32516 (9)	0.57098 (12)	0.80038 (12)	0.0567 (5)
H35	0.2969	0.5453	0.8250	0.068*
C36	0.37552 (9)	0.55248 (13)	0.82104 (12)	0.0615 (6)
H36	0.3817	0.5143	0.8596	0.074*
C37	0.41865 (8)	0.59056 (12)	0.78461 (11)	0.0536 (5)
H37	0.4531	0.5773	0.7995	0.064*
C38	0.41083 (7)	0.64633 (11)	0.72811 (11)	0.0455 (4)
H38	0.4400	0.6709	0.7048	0.055*
C38A	0.35892 (7)	0.66766 (10)	0.70424 (10)	0.0385 (4)
N39	0.35367 (6)	0.72454 (8)	0.64686 (8)	0.0392 (3)
C39A	0.30417 (7)	0.74181 (10)	0.62778 (10)	0.0385 (4)
C311	0.31690 (7)	0.84788 (10)	0.52224 (10)	0.0422 (4)
C312	0.37146 (8)	0.85344 (11)	0.52897 (11)	0.0473 (4)
H312	0.3895	0.8230	0.5663	0.057*
C313	0.39928 (9)	0.90427 (12)	0.48017 (12)	0.0540 (5)
H313	0.4361	0.9078	0.4848	0.065*
C314	0.37313 (10)	0.94998 (13)	0.42443 (12)	0.0622 (6)
H314	0.3920	0.9842	0.3917	0.075*
C315	0.31879 (10)	0.94404 (13)	0.41812 (13)	0.0645 (6)
H315	0.3009	0.9747	0.3808	0.077*
C316	0.29015 (9)	0.89327 (12)	0.46623 (12)	0.0555 (5)
H316	0.2534	0.8895	0.4612	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0276 (7)	0.0431 (8)	0.0371 (7)	0.0014 (6)	−0.0055 (6)	0.0013 (6)
N12	0.0292 (8)	0.0571 (10)	0.0510 (9)	0.0010 (7)	−0.0080 (7)	0.0027 (8)
C13	0.0298 (9)	0.0594 (12)	0.0519 (11)	−0.0049 (8)	−0.0036 (8)	0.0020 (9)
C13A	0.0329 (9)	0.0459 (10)	0.0393 (9)	−0.0040 (7)	−0.0021 (7)	−0.0044 (8)
C14	0.0439 (11)	0.0477 (10)	0.0441 (10)	−0.0109 (8)	0.0016 (8)	0.0005 (8)
C14A	0.0463 (10)	0.0384 (9)	0.0345 (9)	−0.0028 (7)	−0.0027 (7)	−0.0038 (7)
C15	0.0663 (14)	0.0442 (10)	0.0427 (10)	−0.0083 (9)	−0.0017 (9)	0.0040 (8)
C16	0.0777 (15)	0.0424 (10)	0.0421 (10)	0.0052 (10)	−0.0095 (10)	0.0053 (9)
C17	0.0591 (12)	0.0482 (10)	0.0395 (9)	0.0165 (9)	−0.0114 (9)	−0.0052 (8)
C18	0.0424 (10)	0.0460 (10)	0.0341 (9)	0.0077 (8)	−0.0044 (7)	−0.0046 (7)
C18A	0.0424 (10)	0.0354 (8)	0.0282 (8)	0.0038 (7)	−0.0034 (7)	−0.0076 (7)
N19	0.0333 (8)	0.0399 (7)	0.0321 (7)	0.0035 (6)	−0.0034 (6)	−0.0019 (6)
C19A	0.0347 (9)	0.0361 (9)	0.0291 (8)	0.0001 (7)	−0.0036 (7)	−0.0055 (6)
C111	0.0370 (9)	0.0346 (8)	0.0289 (8)	0.0006 (7)	−0.0019 (7)	−0.0041 (6)
C112	0.0361 (10)	0.0455 (10)	0.0371 (9)	0.0035 (7)	−0.0035 (7)	0.0000 (7)
C113	0.0366 (10)	0.0512 (11)	0.0517 (11)	−0.0005 (8)	0.0030 (8)	−0.0001 (9)
C114	0.0531 (12)	0.0431 (10)	0.0467 (10)	−0.0002 (8)	0.0077 (9)	0.0028 (8)
C115	0.0561 (13)	0.0475 (11)	0.0469 (11)	0.0064 (9)	−0.0062 (9)	0.0090 (9)
C116	0.0387 (10)	0.0481 (10)	0.0473 (10)	0.0032 (8)	−0.0080 (8)	0.0041 (8)
N21	0.0342 (8)	0.0427 (8)	0.0375 (7)	−0.0034 (6)	−0.0001 (6)	−0.0036 (6)
N22	0.0360 (8)	0.0554 (9)	0.0455 (8)	−0.0062 (7)	−0.0008 (7)	−0.0018 (7)
C23	0.0346 (10)	0.0548 (11)	0.0441 (10)	−0.0021 (8)	0.0024 (8)	0.0010 (9)
C23A	0.0345 (9)	0.0402 (9)	0.0343 (8)	−0.0016 (7)	0.0045 (7)	0.0066 (7)
C24	0.0425 (10)	0.0389 (9)	0.0362 (9)	0.0019 (7)	0.0094 (7)	0.0028 (7)
C24A	0.0454 (10)	0.0356 (9)	0.0317 (8)	−0.0033 (7)	0.0045 (7)	0.0031 (7)
C25	0.0619 (13)	0.0440 (10)	0.0372 (9)	−0.0031 (9)	0.0085 (9)	−0.0036 (8)
C26	0.0719 (15)	0.0511 (11)	0.0402 (10)	−0.0121 (10)	−0.0025 (10)	−0.0082 (9)
C27	0.0544 (12)	0.0593 (12)	0.0459 (10)	−0.0149 (10)	−0.0088 (9)	−0.0028 (9)
C28	0.0419 (11)	0.0537 (11)	0.0451 (10)	−0.0058 (8)	−0.0017 (8)	−0.0041 (9)
C28A	0.0407 (10)	0.0383 (9)	0.0317 (8)	−0.0037 (7)	0.0009 (7)	0.0022 (7)
N29	0.0360 (8)	0.0411 (8)	0.0379 (7)	−0.0029 (6)	0.0010 (6)	−0.0022 (6)
C29A	0.0368 (9)	0.0349 (8)	0.0292 (8)	−0.0032 (7)	0.0013 (7)	0.0026 (6)
C211	0.0476 (11)	0.0349 (8)	0.0332 (8)	0.0000 (7)	0.0011 (7)	0.0015 (7)
C212	0.0467 (12)	0.0545 (11)	0.0536 (11)	0.0066 (9)	−0.0051 (9)	−0.0122 (9)
C213	0.0548 (13)	0.0690 (14)	0.0693 (14)	0.0175 (11)	0.0006 (11)	−0.0158 (12)
C214	0.0816 (17)	0.0541 (13)	0.0581 (13)	0.0156 (11)	0.0074 (12)	−0.0147 (10)
C215	0.0777 (16)	0.0506 (12)	0.0510 (12)	−0.0053 (11)	0.0005 (11)	−0.0141 (10)
C216	0.0554 (12)	0.0476 (10)	0.0436 (10)	−0.0075 (9)	0.0005 (9)	−0.0056 (8)
N31	0.0386 (9)	0.0451 (8)	0.0489 (9)	0.0054 (7)	−0.0016 (7)	−0.0012 (7)
N32	0.0370 (9)	0.0591 (10)	0.0713 (11)	0.0068 (8)	−0.0037 (8)	−0.0001 (9)
C33	0.0376 (11)	0.0580 (12)	0.0740 (14)	0.0010 (9)	0.0031 (10)	0.0010 (11)
C33A	0.0403 (10)	0.0445 (10)	0.0530 (11)	0.0015 (8)	0.0050 (8)	−0.0078 (9)
C34	0.0445 (11)	0.0486 (11)	0.0571 (11)	−0.0059 (9)	0.0119 (9)	−0.0020 (9)
C34A	0.0472 (11)	0.0419 (10)	0.0448 (10)	0.0013 (8)	0.0066 (8)	−0.0068 (8)
C35	0.0671 (14)	0.0498 (11)	0.0530 (12)	−0.0027 (10)	0.0150 (10)	0.0065 (9)
C36	0.0797 (16)	0.0546 (12)	0.0501 (12)	0.0097 (11)	0.0034 (11)	0.0119 (10)
C37	0.0570 (13)	0.0583 (12)	0.0455 (11)	0.0114 (10)	−0.0029 (9)	0.0015 (9)
C38	0.0444 (11)	0.0496 (11)	0.0425 (10)	0.0030 (8)	0.0004 (8)	−0.0031 (8)
C38A	0.0445 (10)	0.0369 (9)	0.0342 (8)	0.0021 (7)	0.0035 (7)	−0.0069 (7)
N39	0.0381 (8)	0.0406 (8)	0.0387 (8)	0.0024 (6)	0.0021 (6)	−0.0032 (6)
C39A	0.0379 (10)	0.0379 (9)	0.0398 (9)	0.0026 (7)	0.0018 (7)	−0.0084 (7)
C311	0.0488 (11)	0.0392 (9)	0.0386 (9)	0.0052 (8)	0.0039 (8)	−0.0053 (7)
C312	0.0496 (12)	0.0471 (10)	0.0451 (10)	0.0060 (9)	0.0004 (8)	0.0015 (8)
C313	0.0539 (13)	0.0542 (12)	0.0537 (11)	0.0002 (9)	0.0087 (9)	0.0016 (10)
C314	0.0813 (17)	0.0548 (12)	0.0506 (12)	0.0018 (11)	0.0133 (11)	0.0071 (10)
C315	0.0782 (17)	0.0614 (13)	0.0538 (12)	0.0173 (12)	−0.0017 (11)	0.0120 (11)
C316	0.0555 (13)	0.0579 (12)	0.0532 (11)	0.0127 (10)	−0.0029 (10)	0.0032 (10)

Geometric parameters (Å, º)

N11—N12	1.3823 (19)	C27—H27	0.9300
N11—C19A	1.385 (2)	C28—C28A	1.417 (2)
N11—C111	1.417 (2)	C28—H28	0.9300
N12—C13	1.306 (2)	C28A—N29	1.365 (2)
C13—C13A	1.422 (2)	N29—C29A	1.316 (2)
C13—H13	0.9300	C211—C212	1.383 (3)
C13A—C14	1.373 (3)	C211—C216	1.389 (2)
C13A—C19A	1.422 (2)	C212—C213	1.386 (3)
C14—C14A	1.401 (2)	C212—H212	0.9300
C14—H14	0.9300	C213—C214	1.373 (3)
C14A—C15	1.422 (2)	C213—H213	0.9300
C14A—C18A	1.430 (2)	C214—C215	1.373 (3)
C15—C16	1.350 (3)	C214—H214	0.9300
C15—H15	0.9300	C215—C216	1.378 (3)
C16—C17	1.407 (3)	C215—H215	0.9300
C16—H16	0.9300	C216—H216	0.9300
C17—C18	1.362 (2)	N31—N32	1.377 (2)
C17—H17	0.9300	N31—C39A	1.380 (2)
C18—C18A	1.416 (2)	N31—C311	1.423 (2)
C18—H18	0.9300	N32—C33	1.310 (3)
C18A—N19	1.366 (2)	C33—C33A	1.426 (3)
N19—C19A	1.319 (2)	C33—H33	0.9300
C111—C112	1.383 (2)	C33A—C34	1.371 (3)
C111—C116	1.392 (2)	C33A—C39A	1.426 (2)
C112—C113	1.385 (2)	C34—C34A	1.398 (3)
C112—H112	0.9300	C34—H34	0.9300
C113—C114	1.376 (3)	C34A—C35	1.429 (3)
C113—H113	0.9300	C34A—C38A	1.432 (2)
C114—C115	1.377 (3)	C35—C36	1.350 (3)
C114—H114	0.9300	C35—H35	0.9300
C115—C116	1.378 (3)	C36—C37	1.403 (3)
C115—H115	0.9300	C36—H36	0.9300
C116—H116	0.9300	C37—C38	1.355 (3)
N21—C29A	1.384 (2)	C37—H37	0.9300
N21—N22	1.385 (2)	C38—C38A	1.413 (2)
N21—C211	1.419 (2)	C38—H38	0.9300
N22—C23	1.309 (2)	C38A—N39	1.371 (2)
C23—C23A	1.424 (2)	N39—C39A	1.318 (2)
C23—H23	0.9300	C311—C312	1.380 (3)
C23A—C24	1.378 (2)	C311—C316	1.390 (3)
C23A—C29A	1.419 (2)	C312—C313	1.381 (3)
C24—C24A	1.401 (2)	C312—H312	0.9300
C24—H24	0.9300	C313—C314	1.383 (3)
C24A—C25	1.426 (2)	C313—H313	0.9300
C24A—C28A	1.433 (2)	C314—C315	1.374 (3)
C25—C26	1.354 (3)	C314—H314	0.9300
C25—H25	0.9300	C315—C316	1.384 (3)
C26—C27	1.410 (3)	C315—H315	0.9300
C26—H26	0.9300	C316—H316	0.9300
C27—C28	1.358 (3)
N12—N11—C19A	110.15 (13)	C28A—C28—H28	119.7
N12—N11—C111	118.82 (13)	N29—C28A—C28	117.88 (16)
C19A—N11—C111	131.01 (14)	N29—C28A—C24A	123.40 (15)
C13—N12—N11	106.99 (14)	C28—C28A—C24A	118.72 (15)
N12—C13—C13A	112.27 (16)	C29A—N29—C28A	114.63 (14)
N12—C13—H13	123.9	N29—C29A—N21	126.57 (15)
C13A—C13—H13	123.9	N29—C29A—C23A	126.96 (15)
C14—C13A—C13	137.55 (17)	N21—C29A—C23A	106.47 (14)
C14—C13A—C19A	118.37 (16)	C212—C211—C216	119.94 (17)
C13—C13A—C19A	104.07 (15)	C212—C211—N21	120.65 (16)
C13A—C14—C14A	117.87 (16)	C216—C211—N21	119.41 (16)
C13A—C14—H14	121.1	C211—C212—C213	119.14 (19)
C14A—C14—H14	121.1	C211—C212—H212	120.4
C14—C14A—C15	122.60 (17)	C213—C212—H212	120.4
C14—C14A—C18A	118.91 (15)	C214—C213—C212	121.2 (2)
C15—C14A—C18A	118.48 (17)	C214—C213—H213	119.4
C16—C15—C14A	121.42 (19)	C212—C213—H213	119.4
C16—C15—H15	119.3	C215—C214—C213	119.07 (19)
C14A—C15—H15	119.3	C215—C214—H214	120.5
C15—C16—C17	119.95 (18)	C213—C214—H214	120.5
C15—C16—H16	120.0	C214—C215—C216	121.1 (2)
C17—C16—H16	120.0	C214—C215—H215	119.5
C18—C17—C16	120.96 (18)	C216—C215—H215	119.5
C18—C17—H17	119.5	C215—C216—C211	119.53 (19)
C16—C17—H17	119.5	C215—C216—H216	120.2
C17—C18—C18A	120.76 (18)	C211—C216—H216	120.2
C17—C18—H18	119.6	N32—N31—C39A	110.38 (15)
C18A—C18—H18	119.6	N32—N31—C311	118.92 (15)
N19—C18A—C18	117.81 (15)	C39A—N31—C311	130.70 (15)
N19—C18A—C14A	123.76 (15)	C33—N32—N31	107.28 (16)
C18—C18A—C14A	118.43 (15)	N32—C33—C33A	111.84 (18)
C19A—N19—C18A	114.34 (14)	N32—C33—H33	124.1
N19—C19A—N11	126.75 (15)	C33A—C33—H33	124.1
N19—C19A—C13A	126.73 (15)	C34—C33A—C33	137.75 (19)
N11—C19A—C13A	106.52 (14)	C34—C33A—C39A	118.31 (17)
C112—C111—C116	119.80 (16)	C33—C33A—C39A	103.95 (17)
C112—C111—N11	120.68 (15)	C33A—C34—C34A	118.27 (17)
C116—C111—N11	119.51 (15)	C33A—C34—H34	120.9
C111—C112—C113	119.55 (16)	C34A—C34—H34	120.9
C111—C112—H112	120.2	C34—C34A—C35	122.89 (18)
C113—C112—H112	120.2	C34—C34A—C38A	118.92 (17)
C114—C113—C112	120.98 (17)	C35—C34A—C38A	118.19 (17)
C114—C113—H113	119.5	C36—C35—C34A	120.96 (19)
C112—C113—H113	119.5	C36—C35—H35	119.5
C113—C114—C115	119.00 (18)	C34A—C35—H35	119.5
C113—C114—H114	120.5	C35—C36—C37	120.37 (19)
C115—C114—H114	120.5	C35—C36—H36	119.8
C114—C115—C116	121.22 (17)	C37—C36—H36	119.8
C114—C115—H115	119.4	C38—C37—C36	121.03 (19)
C116—C115—H115	119.4	C38—C37—H37	119.5
C115—C116—C111	119.44 (17)	C36—C37—H37	119.5
C115—C116—H116	120.3	C37—C38—C38A	120.80 (18)
C111—C116—H116	120.3	C37—C38—H38	119.6
C29A—N21—N22	110.27 (13)	C38A—C38—H38	119.6
C29A—N21—C211	130.67 (14)	N39—C38A—C38	117.99 (16)
N22—N21—C211	119.05 (14)	N39—C38A—C34A	123.35 (16)
C23—N22—N21	106.89 (14)	C38—C38A—C34A	118.65 (16)
N22—C23—C23A	112.01 (16)	C39A—N39—C38A	114.75 (15)
N22—C23—H23	124.0	N39—C39A—N31	127.05 (16)
C23A—C23—H23	124.0	N39—C39A—C33A	126.40 (17)
C24—C23A—C29A	118.10 (15)	N31—C39A—C33A	106.55 (15)
C24—C23A—C23	137.54 (16)	C312—C311—C316	119.93 (18)
C29A—C23A—C23	104.35 (15)	C312—C311—N31	120.82 (16)
C23A—C24—C24A	117.92 (15)	C316—C311—N31	119.25 (17)
C23A—C24—H24	121.0	C311—C312—C313	119.85 (18)
C24A—C24—H24	121.0	C311—C312—H312	120.1
C24—C24A—C25	122.68 (16)	C313—C312—H312	120.1
C24—C24A—C28A	118.98 (15)	C312—C313—C314	120.8 (2)
C25—C24A—C28A	118.34 (16)	C312—C313—H313	119.6
C26—C25—C24A	120.99 (18)	C314—C313—H313	119.6
C26—C25—H25	119.5	C315—C314—C313	119.0 (2)
C24A—C25—H25	119.5	C315—C314—H314	120.5
C25—C26—C27	120.33 (18)	C313—C314—H314	120.5
C25—C26—H26	119.8	C314—C315—C316	121.2 (2)
C27—C26—H26	119.8	C314—C315—H315	119.4
C28—C27—C26	120.91 (18)	C316—C315—H315	119.4
C28—C27—H27	119.5	C315—C316—C311	119.3 (2)
C26—C27—H27	119.5	C315—C316—H316	120.4
C27—C28—C28A	120.69 (18)	C311—C316—H316	120.4
C27—C28—H28	119.7
C19A—N11—N12—C13	0.05 (19)	C28A—N29—C29A—N21	−179.08 (15)
C111—N11—N12—C13	178.71 (15)	C28A—N29—C29A—C23A	0.6 (2)
N11—N12—C13—C13A	−0.2 (2)	N22—N21—C29A—N29	−179.43 (15)
N12—C13—C13A—C14	−178.5 (2)	C211—N21—C29A—N29	1.4 (3)
N12—C13—C13A—C19A	0.3 (2)	N22—N21—C29A—C23A	0.82 (18)
C13—C13A—C14—C14A	179.1 (2)	C211—N21—C29A—C23A	−178.39 (16)
C19A—C13A—C14—C14A	0.5 (2)	C24—C23A—C29A—N29	−1.3 (2)
C13A—C14—C14A—C15	179.71 (16)	C23—C23A—C29A—N29	179.52 (16)
C13A—C14—C14A—C18A	0.5 (2)	C24—C23A—C29A—N21	178.44 (14)
C14—C14A—C15—C16	−178.94 (18)	C23—C23A—C29A—N21	−0.72 (17)
C18A—C14A—C15—C16	0.3 (3)	C29A—N21—C211—C212	0.2 (3)
C14A—C15—C16—C17	0.5 (3)	N22—N21—C211—C212	−178.96 (16)
C15—C16—C17—C18	−0.8 (3)	C29A—N21—C211—C216	−179.25 (16)
C16—C17—C18—C18A	0.2 (3)	N22—N21—C211—C216	1.6 (2)
C17—C18—C18A—N19	−179.76 (15)	C216—C211—C212—C213	0.2 (3)
C17—C18—C18A—C14A	0.6 (2)	N21—C211—C212—C213	−179.19 (18)
C14—C14A—C18A—N19	−1.2 (2)	C211—C212—C213—C214	−0.1 (3)
C15—C14A—C18A—N19	179.55 (15)	C212—C213—C214—C215	−0.1 (4)
C14—C14A—C18A—C18	178.40 (15)	C213—C214—C215—C216	0.2 (3)
C15—C14A—C18A—C18	−0.8 (2)	C214—C215—C216—C211	−0.1 (3)
C18—C18A—N19—C19A	−178.84 (14)	C212—C211—C216—C215	−0.2 (3)
C14A—C18A—N19—C19A	0.8 (2)	N21—C211—C216—C215	179.29 (17)
C18A—N19—C19A—N11	−179.46 (14)	C39A—N31—N32—C33	0.0 (2)
C18A—N19—C19A—C13A	0.3 (2)	C311—N31—N32—C33	−179.29 (16)
N12—N11—C19A—N19	179.94 (15)	N31—N32—C33—C33A	−0.1 (2)
C111—N11—C19A—N19	1.5 (3)	N32—C33—C33A—C34	−179.6 (2)
N12—N11—C19A—C13A	0.11 (18)	N32—C33—C33A—C39A	0.1 (2)
C111—N11—C19A—C13A	−178.33 (15)	C33—C33A—C34—C34A	−179.9 (2)
C14—C13A—C19A—N19	−1.0 (3)	C39A—C33A—C34—C34A	0.5 (3)
C13—C13A—C19A—N19	179.95 (16)	C33A—C34—C34A—C35	179.89 (18)
C14—C13A—C19A—N11	178.85 (15)	C33A—C34—C34A—C38A	−0.3 (3)
C13—C13A—C19A—N11	−0.22 (17)	C34—C34A—C35—C36	−179.87 (19)
N12—N11—C111—C112	176.94 (15)	C38A—C34A—C35—C36	0.4 (3)
C19A—N11—C111—C112	−4.7 (3)	C34A—C35—C36—C37	0.0 (3)
N12—N11—C111—C116	−2.2 (2)	C35—C36—C37—C38	−0.1 (3)
C19A—N11—C111—C116	176.08 (16)	C36—C37—C38—C38A	−0.1 (3)
C116—C111—C112—C113	0.7 (2)	C37—C38—C38A—N39	179.94 (17)
N11—C111—C112—C113	−178.53 (15)	C37—C38—C38A—C34A	0.4 (3)
C111—C112—C113—C114	−0.1 (3)	C34—C34A—C38A—N39	0.2 (3)
C112—C113—C114—C115	−0.5 (3)	C35—C34A—C38A—N39	179.94 (16)
C113—C114—C115—C116	0.5 (3)	C34—C34A—C38A—C38	179.71 (17)
C114—C115—C116—C111	0.0 (3)	C35—C34A—C38A—C38	−0.5 (2)
C112—C111—C116—C115	−0.6 (3)	C38—C38A—N39—C39A	−179.66 (15)
N11—C111—C116—C115	178.58 (16)	C34A—C38A—N39—C39A	−0.1 (2)
C29A—N21—N22—C23	−0.57 (19)	C38A—N39—C39A—N31	−179.93 (15)
C211—N21—N22—C23	178.75 (15)	C38A—N39—C39A—C33A	0.3 (2)
N21—N22—C23—C23A	0.1 (2)	N32—N31—C39A—N39	−179.82 (16)
N22—C23—C23A—C24	−178.50 (19)	C311—N31—C39A—N39	−0.6 (3)
N22—C23—C23A—C29A	0.40 (19)	N32—N31—C39A—C33A	0.03 (19)
C29A—C23A—C24—C24A	0.6 (2)	C311—N31—C39A—C33A	179.23 (17)
C23—C23A—C24—C24A	179.44 (19)	C34—C33A—C39A—N39	−0.4 (3)
C23A—C24—C24A—C25	−179.96 (16)	C33—C33A—C39A—N39	179.79 (17)
C23A—C24—C24A—C28A	0.5 (2)	C34—C33A—C39A—N31	179.70 (16)
C24—C24A—C25—C26	−178.45 (17)	C33—C33A—C39A—N31	−0.06 (19)
C28A—C24A—C25—C26	1.1 (3)	N32—N31—C311—C312	173.78 (17)
C24A—C25—C26—C27	0.3 (3)	C39A—N31—C311—C312	−5.4 (3)
C25—C26—C27—C28	−1.4 (3)	N32—N31—C311—C316	−6.0 (2)
C26—C27—C28—C28A	1.1 (3)	C39A—N31—C311—C316	174.88 (18)
C27—C28—C28A—N29	179.77 (17)	C316—C311—C312—C313	0.2 (3)
C27—C28—C28A—C24A	0.3 (3)	N31—C311—C312—C313	−179.56 (17)
C24—C24A—C28A—N29	−1.2 (2)	C311—C312—C313—C314	0.1 (3)
C25—C24A—C28A—N29	179.20 (15)	C312—C313—C314—C315	−0.1 (3)
C24—C24A—C28A—C28	178.19 (16)	C313—C314—C315—C316	−0.1 (3)
C25—C24A—C28A—C28	−1.4 (2)	C314—C315—C316—C311	0.4 (3)
C28—C28A—N29—C29A	−178.76 (15)	C312—C311—C316—C315	−0.4 (3)
C24A—C28A—N29—C29A	0.7 (2)	N31—C311—C316—C315	179.34 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···Cg3^i	0.93	2.84	3.716 (2)	157
C26—H26···Cg4	0.93	2.94	3.795 (2)	154

Symmetry code: (i) x, −y+1, z+1/2.

(IV) 6-Methyl-1-phenyl-1H-pyrazolo[3,4-b]quinoline

Crystal data

C17H13N3	Dx = 1.354 Mg m^−3
Mr = 259.30	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3:H	Cell parameters from 3437 reflections
a = 29.9202 (12) Å	θ = 2.4–30.3°
c = 7.3811 (3) Å	µ = 0.08 mm^−1
V = 5722.4 (5) Å^3	T = 296 K
Z = 18	Block, colourless
F(000) = 2448	0.42 × 0.26 × 0.14 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer	2077 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	Rint = 0.097
φ and ω scans	θmax = 27.6°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −38→36
Tmin = 0.978, Tmax = 0.988	k = −38→38
17651 measured reflections	l = −9→9
2942 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.0742P)^2 + 4.6125P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.173	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.22 e Å^−3
2942 reflections	Δρmin = −0.20 e Å^−3
183 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0006 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.43257 (6)	0.28207 (6)	0.4528 (2)	0.0390 (4)
N2	0.41980 (7)	0.31916 (6)	0.4071 (2)	0.0466 (5)
C3	0.37090 (8)	0.29442 (8)	0.3617 (3)	0.0461 (5)
H3	0.3527	0.3106	0.3249	0.055*
C3A	0.34878 (7)	0.23988 (7)	0.3750 (3)	0.0388 (5)
C4	0.30184 (7)	0.19673 (8)	0.3434 (3)	0.0402 (5)
H4	0.2741	0.1995	0.3004	0.048*
C4A	0.29689 (7)	0.14837 (7)	0.3780 (2)	0.0359 (4)
C5	0.24970 (7)	0.10132 (8)	0.3539 (3)	0.0405 (5)
H5	0.2211	0.1026	0.3113	0.049*
C6	0.24463 (7)	0.05443 (7)	0.3907 (3)	0.0406 (5)
C7	0.28895 (8)	0.05326 (8)	0.4524 (3)	0.0426 (5)
H7	0.2862	0.0215	0.4775	0.051*
C8	0.33536 (7)	0.09705 (7)	0.4759 (3)	0.0408 (5)
H8	0.3636	0.0946	0.5157	0.049*
C8A	0.34122 (7)	0.14632 (7)	0.4404 (2)	0.0349 (4)
N9	0.38851 (6)	0.18886 (6)	0.4680 (2)	0.0360 (4)
C9A	0.39014 (7)	0.23301 (7)	0.4355 (2)	0.0354 (4)
C11	0.48437 (7)	0.29814 (7)	0.4980 (2)	0.0365 (4)
C12	0.49663 (8)	0.26581 (7)	0.5928 (3)	0.0414 (5)
H12	0.4708	0.2330	0.6270	0.050*
C13	0.54775 (8)	0.28264 (8)	0.6365 (3)	0.0500 (5)
H13	0.5561	0.2610	0.7003	0.060*
C14	0.58628 (8)	0.33119 (8)	0.5863 (3)	0.0530 (6)
H14	0.6204	0.3422	0.6164	0.064*
C15	0.57403 (8)	0.36335 (8)	0.4912 (3)	0.0497 (5)
H15	0.6001	0.3960	0.4571	0.060*
C16	0.52344 (8)	0.34733 (7)	0.4462 (3)	0.0431 (5)
H16	0.5154	0.3691	0.3819	0.052*
C61	0.19410 (8)	0.00502 (8)	0.3690 (3)	0.0502 (5)
H61A	0.1821	−0.0108	0.4855	0.075*
H61B	0.1988	−0.0180	0.2915	0.075*
H61C	0.1691	0.0123	0.3163	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0381 (9)	0.0310 (8)	0.0484 (9)	0.0176 (7)	0.0021 (7)	0.0026 (7)
N2	0.0501 (11)	0.0357 (9)	0.0588 (11)	0.0250 (8)	0.0030 (8)	0.0037 (8)
C3	0.0459 (12)	0.0415 (11)	0.0594 (13)	0.0283 (10)	0.0041 (9)	0.0072 (9)
C3A	0.0409 (11)	0.0376 (10)	0.0421 (10)	0.0228 (9)	0.0052 (8)	0.0031 (8)
C4	0.0367 (10)	0.0474 (11)	0.0430 (11)	0.0259 (9)	0.0017 (8)	0.0033 (8)
C4A	0.0335 (9)	0.0401 (10)	0.0345 (9)	0.0188 (8)	0.0022 (7)	0.0004 (8)
C5	0.0324 (10)	0.0462 (11)	0.0417 (11)	0.0187 (9)	−0.0013 (8)	−0.0007 (8)
C6	0.0364 (10)	0.0403 (11)	0.0398 (10)	0.0151 (8)	0.0028 (8)	−0.0036 (8)
C7	0.0414 (11)	0.0342 (10)	0.0493 (11)	0.0168 (9)	−0.0001 (9)	0.0008 (8)
C8	0.0365 (10)	0.0372 (10)	0.0502 (11)	0.0197 (8)	−0.0018 (8)	0.0005 (8)
C8A	0.0342 (10)	0.0364 (10)	0.0344 (9)	0.0178 (8)	0.0017 (7)	−0.0011 (7)
N9	0.0343 (8)	0.0315 (8)	0.0415 (9)	0.0159 (7)	0.0004 (6)	0.0009 (6)
C9A	0.0359 (10)	0.0344 (10)	0.0361 (9)	0.0178 (8)	0.0034 (7)	0.0002 (7)
C11	0.0373 (10)	0.0348 (10)	0.0360 (10)	0.0169 (8)	0.0020 (7)	−0.0047 (7)
C12	0.0403 (11)	0.0327 (10)	0.0475 (11)	0.0155 (8)	−0.0010 (8)	−0.0017 (8)
C13	0.0492 (13)	0.0412 (11)	0.0589 (13)	0.0220 (10)	−0.0101 (10)	−0.0035 (9)
C14	0.0396 (11)	0.0460 (12)	0.0666 (14)	0.0163 (10)	−0.0082 (10)	−0.0098 (10)
C15	0.0417 (11)	0.0376 (11)	0.0565 (13)	0.0099 (9)	0.0026 (9)	−0.0012 (9)
C16	0.0452 (11)	0.0350 (10)	0.0454 (11)	0.0173 (9)	0.0017 (9)	0.0009 (8)
C61	0.0384 (11)	0.0445 (12)	0.0576 (13)	0.0132 (9)	0.0012 (9)	−0.0075 (10)

Geometric parameters (Å, º)

N1—N2	1.384 (2)	C8—C8A	1.419 (3)
N1—C9A	1.385 (2)	C8—H8	0.9300
N1—C11	1.414 (2)	C8A—N9	1.365 (2)
N2—C3	1.311 (3)	N9—C9A	1.320 (2)
C3—C3A	1.425 (3)	C11—C12	1.384 (3)
C3—H3	0.9300	C11—C16	1.399 (3)
C3A—C4	1.371 (3)	C12—C13	1.388 (3)
C3A—C9A	1.424 (3)	C12—H12	0.9300
C4—C4A	1.402 (3)	C13—C14	1.379 (3)
C4—H4	0.9300	C13—H13	0.9300
C4A—C5	1.421 (3)	C14—C15	1.380 (3)
C4A—C8A	1.434 (3)	C14—H14	0.9300
C5—C6	1.361 (3)	C15—C16	1.381 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.419 (3)	C16—H16	0.9300
C6—C61	1.504 (3)	C61—H61A	0.9600
C7—C8	1.362 (3)	C61—H61B	0.9600
C7—H7	0.9300	C61—H61C	0.9600
N2—N1—C9A	110.67 (15)	C8—C8A—C4A	117.85 (17)
N2—N1—C11	118.68 (15)	C9A—N9—C8A	114.12 (16)
C9A—N1—C11	130.55 (16)	N9—C9A—N1	126.84 (17)
C3—N2—N1	106.70 (16)	N9—C9A—C3A	127.00 (17)
N2—C3—C3A	112.15 (17)	N1—C9A—C3A	106.16 (16)
N2—C3—H3	123.9	C12—C11—C16	119.97 (18)
C3A—C3—H3	123.9	C12—C11—N1	120.68 (17)
C4—C3A—C9A	118.19 (17)	C16—C11—N1	119.35 (17)
C4—C3A—C3	137.48 (19)	C11—C12—C13	119.53 (18)
C9A—C3A—C3	104.32 (17)	C11—C12—H12	120.2
C3A—C4—C4A	118.07 (17)	C13—C12—H12	120.2
C3A—C4—H4	121.0	C14—C13—C12	120.6 (2)
C4A—C4—H4	121.0	C14—C13—H13	119.7
C4—C4A—C5	122.64 (17)	C12—C13—H13	119.7
C4—C4A—C8A	118.68 (17)	C13—C14—C15	119.8 (2)
C5—C4A—C8A	118.69 (17)	C13—C14—H14	120.1
C6—C5—C4A	122.66 (18)	C15—C14—H14	120.1
C6—C5—H5	118.7	C14—C15—C16	120.50 (19)
C4A—C5—H5	118.7	C14—C15—H15	119.8
C5—C6—C7	117.75 (18)	C16—C15—H15	119.8
C5—C6—C61	122.09 (18)	C15—C16—C11	119.58 (19)
C7—C6—C61	120.16 (18)	C15—C16—H16	120.2
C8—C7—C6	122.21 (18)	C11—C16—H16	120.2
C8—C7—H7	118.9	C6—C61—H61A	109.5
C6—C7—H7	118.9	C6—C61—H61B	109.5
C7—C8—C8A	120.84 (18)	H61A—C61—H61B	109.5
C7—C8—H8	119.6	C6—C61—H61C	109.5
C8A—C8—H8	119.6	H61A—C61—H61C	109.5
N9—C8A—C8	118.24 (16)	H61B—C61—H61C	109.5
N9—C8A—C4A	123.91 (16)
C9A—N1—N2—C3	−0.3 (2)	C4A—C8A—N9—C9A	1.2 (3)
C11—N1—N2—C3	176.52 (16)	C8A—N9—C9A—N1	179.65 (17)
N1—N2—C3—C3A	0.1 (2)	C8A—N9—C9A—C3A	−0.6 (3)
N2—C3—C3A—C4	−178.6 (2)	N2—N1—C9A—N9	−179.91 (17)
N2—C3—C3A—C9A	0.1 (2)	C11—N1—C9A—N9	3.8 (3)
C9A—C3A—C4—C4A	1.9 (3)	N2—N1—C9A—C3A	0.3 (2)
C3—C3A—C4—C4A	−179.5 (2)	C11—N1—C9A—C3A	−175.97 (18)
C3A—C4—C4A—C5	178.50 (17)	C4—C3A—C9A—N9	−1.0 (3)
C3A—C4—C4A—C8A	−1.4 (3)	C3—C3A—C9A—N9	179.99 (18)
C4—C4A—C5—C6	−178.70 (18)	C4—C3A—C9A—N1	178.79 (16)
C8A—C4A—C5—C6	1.2 (3)	C3—C3A—C9A—N1	−0.2 (2)
C4A—C5—C6—C7	−1.2 (3)	N2—N1—C11—C12	161.33 (17)
C4A—C5—C6—C61	178.45 (18)	C9A—N1—C11—C12	−22.6 (3)
C5—C6—C7—C8	0.3 (3)	N2—N1—C11—C16	−18.6 (2)
C61—C6—C7—C8	−179.29 (19)	C9A—N1—C11—C16	157.44 (19)
C6—C7—C8—C8A	0.5 (3)	C16—C11—C12—C13	0.3 (3)
C7—C8—C8A—N9	179.37 (17)	N1—C11—C12—C13	−179.61 (18)
C7—C8—C8A—C4A	−0.4 (3)	C11—C12—C13—C14	0.0 (3)
C4—C4A—C8A—N9	−0.2 (3)	C12—C13—C14—C15	−0.2 (3)
C5—C4A—C8A—N9	179.85 (16)	C13—C14—C15—C16	0.1 (3)
C4—C4A—C8A—C8	179.55 (17)	C14—C15—C16—C11	0.1 (3)
C5—C4A—C8A—C8	−0.4 (3)	C12—C11—C16—C15	−0.4 (3)
C8—C8A—N9—C9A	−178.58 (16)	N1—C11—C16—C15	179.55 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg2^i	0.93	2.86	3.585 (2)	136

Symmetry code: (i) y+1/3, −x+y+2/3, −z+2/3.