1,3-Diphenyl-8-trifluoro-methyl-1H-pyrazolo-[3,4-b]quinoline.

The 1H-pyrazolo-[3,4-b]quinoline (PQ) core of the title mol-ecule, C(23)H(14)F(3)N(3), is aromatic and essentially planar (r.m.s. deviation = 0.015 Å) and the two phenyl substituents at positions 1 and 3 are twisted relative to this fragment by 29.74 (7) and 25.63 (7)°, respectively. In the crystal, mol-ecules are arranged along the b axis into stacks via π-π inter-actions, with an inter-planar distance of the PQ core of 3.489 (4) Å.

Related literature

For selected photophysical properties of trifluoro­methyl derivatives of 1H-pyrazolo-[3,4-b]quinoline, see: Koścień, Gondek, Jarosz et al. (2009 ▶); Koścień, Gondek, Pokladko et al. (2009 ▶). For the use of trifluoro­methyl derivatives of 1H-pyrazolo-[3,4-b]quinoline in organic light-emitting diode (OLED) preparation, see: Tao et al. (2001 ▶). For the synthesis of 1H-pyrazolo-[3,4-b]quinoline derivatives, see: Brack (1965 ▶).

Experimental

Crystal data

C23H14F3N3

M = 389.37

Monoclinic,

a = 11.8299 (5) Å

b = 6.9788 (3) Å

c = 12.1306 (4) Å

β = 112.765 (2)°

V = 923.47 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.27 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.972, T max = 0.979

4497 measured reflections

4497 independent reflections

2183 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.104

S = 1.05

2876 reflections

262 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028206/gk2493sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028206/gk2493Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028206/gk2493Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H14F3N3	F(000) = 400
Mr = 389.37	Dx = 1.400 Mg m−3
Monoclinic, P21	Melting point = 452–454 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.8299 (5) Å	Cell parameters from 2631 reflections
b = 6.9788 (3) Å	θ = 0.1–30.0°
c = 12.1306 (4) Å	µ = 0.11 mm−1
β = 112.765 (2)°	T = 293 K
V = 923.47 (6) Å3	Block, yellow
Z = 2	0.27 × 0.25 × 0.20 mm

Nonius KappaCCD diffractometer	4497 independent reflections
Radiation source: fine-focus sealed tube	2183 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.018
Detector resolution: 9 pixels mm-1	θmax = 30.0°, θmin = 3.1°
ω scans	h = −16→16
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	k = −8→9
Tmin = 0.972, Tmax = 0.979	l = −17→16
4497 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.1305P] where P = (Fo2 + 2Fc2)/3
2876 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.18 e Å−3
0 constraints

Geometry. All e.s.d.'s are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry.

Refinement. Refinement of F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on all data will be even larger.

	x	y	z	Uiso*/Ueq
N1	−0.18386 (15)	0.2365 (4)	0.65903 (14)	0.0473 (4)
N2	−0.30046 (15)	0.2283 (3)	0.57218 (15)	0.0491 (4)
C3	−0.29086 (18)	0.2297 (4)	0.46736 (18)	0.0454 (5)
C3A	−0.16388 (17)	0.2389 (4)	0.48271 (16)	0.0422 (4)
C4	−0.09599 (18)	0.2371 (4)	0.41296 (17)	0.0453 (5)
H4	−0.1342	0.2327	0.3301	0.054*
C4A	0.03230 (18)	0.2421 (4)	0.46963 (16)	0.0432 (4)
C5	0.1094 (2)	0.2426 (5)	0.40413 (18)	0.0518 (5)
H5	0.0743	0.2407	0.3210	0.062*
C6	0.2333 (2)	0.2456 (5)	0.4611 (2)	0.0572 (6)
H6	0.2822	0.2441	0.4168	0.069*
C7	0.28812 (19)	0.2510 (5)	0.5865 (2)	0.0535 (5)
H7	0.3731	0.2536	0.6242	0.064*
C8	0.21850 (18)	0.2525 (4)	0.65379 (17)	0.0455 (4)
C8A	0.08787 (17)	0.2470 (4)	0.59753 (16)	0.0410 (4)
N9	0.02219 (14)	0.2477 (3)	0.66801 (13)	0.0434 (4)
C9A	−0.09735 (18)	0.2432 (4)	0.60926 (16)	0.0417 (4)
C11	−0.16788 (19)	0.2393 (4)	0.78184 (17)	0.0477 (5)
C12	−0.0697 (2)	0.3313 (4)	0.8651 (2)	0.0593 (7)
H12	−0.0100	0.3868	0.8431	0.071*
C13	−0.0599 (3)	0.3410 (5)	0.9832 (2)	0.0719 (8)
H13	0.0068	0.4025	1.0405	0.086*
C14	−0.1485 (3)	0.2596 (6)	1.0149 (2)	0.0756 (8)
H14	−0.1428	0.2686	1.0934	0.091*
C15	−0.2448 (3)	0.1658 (6)	0.9320 (3)	0.0766 (9)
H15	−0.3035	0.1091	0.9549	0.092*
C16	−0.2567 (3)	0.1534 (5)	0.8135 (2)	0.0639 (7)
H16	−0.3226	0.0892	0.7570	0.077*
C31	−0.40125 (19)	0.2166 (4)	0.3563 (2)	0.0486 (5)
C32	−0.5081 (2)	0.1333 (5)	0.3575 (2)	0.0594 (6)
H32	−0.5100	0.0878	0.4288	0.071*
C33	−0.6107 (2)	0.1185 (5)	0.2531 (3)	0.0720 (8)
H33	−0.6818	0.0641	0.2547	0.086*
C34	−0.6094 (3)	0.1835 (5)	0.1461 (3)	0.0775 (10)
H34	−0.6788	0.1721	0.0759	0.093*
C35	−0.5043 (2)	0.2654 (7)	0.1446 (2)	0.0779 (9)
H35	−0.5026	0.3098	0.0730	0.093*
C36	−0.4008 (2)	0.2820 (5)	0.2494 (2)	0.0614 (7)
H36	−0.3302	0.3380	0.2474	0.074*
C80	0.2782 (2)	0.2633 (5)	0.7870 (2)	0.0567 (6)
F81	0.24588 (17)	0.4210 (3)	0.83109 (15)	0.0736 (5)
F82	0.25008 (17)	0.1139 (3)	0.84136 (15)	0.0723 (5)
F83	0.40032 (12)	0.2662 (4)	0.82621 (13)	0.0813 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0495 (9)	0.0539 (11)	0.0428 (8)	0.0010 (12)	0.0225 (7)	0.0000 (11)
N2	0.0477 (9)	0.0514 (11)	0.0502 (9)	0.0000 (11)	0.0211 (7)	0.0007 (11)
C3	0.0494 (10)	0.0415 (12)	0.0457 (10)	−0.0017 (12)	0.0190 (8)	0.0002 (11)
C3A	0.0477 (9)	0.0385 (10)	0.0405 (9)	−0.0031 (12)	0.0172 (8)	−0.0024 (11)
C4	0.0548 (11)	0.0457 (12)	0.0362 (8)	−0.0032 (13)	0.0183 (8)	−0.0025 (12)
C4A	0.0525 (10)	0.0392 (10)	0.0422 (9)	−0.0029 (12)	0.0231 (8)	−0.0025 (11)
C5	0.0632 (12)	0.0531 (13)	0.0481 (10)	−0.0026 (16)	0.0313 (10)	−0.0034 (15)
C6	0.0622 (13)	0.0584 (15)	0.0646 (13)	−0.0020 (17)	0.0395 (11)	−0.0050 (17)
C7	0.0488 (10)	0.0507 (13)	0.0651 (12)	−0.0026 (14)	0.0268 (10)	−0.0041 (15)
C8	0.0490 (10)	0.0386 (10)	0.0494 (10)	−0.0003 (12)	0.0195 (8)	−0.0034 (12)
C8A	0.0496 (10)	0.0335 (9)	0.0436 (9)	0.0001 (12)	0.0220 (8)	−0.0022 (11)
N9	0.0489 (8)	0.0445 (9)	0.0388 (7)	−0.0008 (11)	0.0191 (7)	−0.0026 (10)
C9A	0.0502 (10)	0.0388 (10)	0.0405 (9)	−0.0013 (12)	0.0223 (8)	−0.0018 (12)
C11	0.0608 (11)	0.0456 (11)	0.0433 (9)	0.0046 (14)	0.0274 (9)	0.0027 (13)
C12	0.0760 (16)	0.0589 (16)	0.0523 (13)	−0.0056 (14)	0.0351 (12)	−0.0023 (12)
C13	0.095 (2)	0.075 (2)	0.0485 (13)	−0.0102 (17)	0.0306 (14)	−0.0091 (14)
C14	0.106 (2)	0.084 (2)	0.0499 (12)	0.009 (2)	0.0448 (14)	0.0019 (17)
C15	0.0898 (19)	0.092 (2)	0.0646 (16)	−0.0012 (19)	0.0481 (16)	0.0157 (17)
C16	0.0735 (16)	0.0687 (18)	0.0587 (14)	−0.0023 (15)	0.0355 (13)	0.0074 (14)
C31	0.0464 (10)	0.0454 (14)	0.0520 (11)	0.0004 (11)	0.0169 (9)	−0.0019 (11)
C32	0.0515 (12)	0.0652 (16)	0.0629 (14)	−0.0039 (14)	0.0238 (11)	−0.0039 (14)
C33	0.0528 (14)	0.080 (2)	0.0799 (19)	−0.0115 (16)	0.0221 (13)	−0.0157 (18)
C34	0.0588 (15)	0.093 (3)	0.0647 (16)	−0.0047 (17)	0.0059 (12)	−0.0165 (17)
C35	0.0726 (16)	0.097 (3)	0.0521 (13)	−0.003 (2)	0.0114 (12)	0.0035 (19)
C36	0.0565 (12)	0.0682 (19)	0.0554 (13)	−0.0052 (14)	0.0170 (10)	0.0059 (13)
C80	0.0538 (12)	0.0606 (16)	0.0529 (11)	0.0031 (15)	0.0176 (10)	−0.0045 (14)
F81	0.0799 (12)	0.0745 (11)	0.0595 (10)	0.0008 (10)	0.0192 (9)	−0.0227 (9)
F82	0.0823 (12)	0.0769 (12)	0.0544 (9)	0.0061 (10)	0.0226 (9)	0.0131 (9)
F83	0.0526 (7)	0.1111 (15)	0.0676 (8)	−0.0001 (12)	0.0093 (6)	−0.0062 (12)

N1—C9A	1.376 (2)	C12—C13	1.393 (3)
N1—N2	1.375 (2)	C12—H12	0.9300
N1—C11	1.427 (2)	C13—C14	1.372 (4)
N2—C3	1.320 (3)	C13—H13	0.9300
C3—C3A	1.442 (3)	C14—C15	1.361 (4)
C3—C31	1.472 (3)	C14—H14	0.9300
C3A—C4	1.374 (3)	C15—C16	1.392 (4)
C3A—C9A	1.429 (3)	C15—H15	0.9300
C4—C4A	1.403 (3)	C16—H16	0.9300
C4—H4	0.9300	C31—C36	1.378 (3)
C4A—C5	1.422 (3)	C31—C32	1.396 (3)
C4A—C8A	1.432 (3)	C32—C33	1.378 (4)
C5—C6	1.358 (3)	C32—H32	0.9300
C5—H5	0.9300	C33—C34	1.380 (5)
C6—C7	1.404 (3)	C33—H33	0.9300
C6—H6	0.9300	C34—C35	1.375 (4)
C7—C8	1.366 (3)	C34—H34	0.9300
C7—H7	0.9300	C35—C36	1.387 (3)
C8—C8A	1.428 (3)	C35—H35	0.9300
C8—C80	1.494 (3)	C36—H36	0.9300
C8A—N9	1.360 (2)	C80—F83	1.335 (3)
N9—C9A	1.315 (2)	C80—F82	1.343 (4)
C11—C12	1.369 (3)	C80—F81	1.343 (4)
C11—C16	1.387 (3)
N9···F82	2.859 (3)	N9···C80	2.808 (3)
N9···F81	2.886 (2)
C9A—N1—N2	111.17 (15)	C13—C12—H12	120.3
C9A—N1—C11	129.57 (17)	C14—C13—C12	120.0 (3)
N2—N1—C11	119.25 (15)	C14—C13—H13	120.0
C3—N2—N1	107.64 (16)	C12—C13—H13	120.0
N2—C3—C3A	110.47 (17)	C15—C14—C13	120.3 (2)
N2—C3—C31	120.29 (18)	C15—C14—H14	119.9
C3A—C3—C31	129.21 (18)	C13—C14—H14	119.9
C4—C3A—C9A	116.85 (17)	C14—C15—C16	121.0 (3)
C4—C3A—C3	138.44 (18)	C14—C15—H15	119.5
C9A—C3A—C3	104.65 (15)	C16—C15—H15	119.5
C3A—C4—C4A	118.50 (17)	C11—C16—C15	118.4 (3)
C3A—C4—H4	120.8	C11—C16—H16	120.8
C4A—C4—H4	120.8	C15—C16—H16	120.8
C4—C4A—C5	122.12 (17)	C36—C31—C32	118.8 (2)
C4—C4A—C8A	119.17 (16)	C36—C31—C3	121.0 (2)
C5—C4A—C8A	118.71 (18)	C32—C31—C3	120.2 (2)
C6—C5—C4A	121.01 (19)	C33—C32—C31	120.1 (3)
C6—C5—H5	119.5	C33—C32—H32	120.0
C4A—C5—H5	119.5	C31—C32—H32	120.0
C5—C6—C7	120.43 (18)	C34—C33—C32	120.9 (3)
C5—C6—H6	119.8	C34—C33—H33	119.6
C7—C6—H6	119.8	C32—C33—H33	119.6
C8—C7—C6	121.0 (2)	C35—C34—C33	119.2 (3)
C8—C7—H7	119.5	C35—C34—H34	120.4
C6—C7—H7	119.5	C33—C34—H34	120.4
C7—C8—C8A	120.35 (19)	C34—C35—C36	120.3 (3)
C7—C8—C80	120.32 (19)	C34—C35—H35	119.8
C8A—C8—C80	119.32 (17)	C36—C35—H35	119.8
N9—C8A—C8	118.39 (17)	C31—C36—C35	120.7 (3)
N9—C8A—C4A	123.15 (17)	C31—C36—H36	119.6
C8—C8A—C4A	118.47 (16)	C35—C36—H36	119.6
C9A—N9—C8A	114.56 (16)	F83—C80—F82	106.0 (2)
N9—C9A—N1	126.14 (16)	F83—C80—F81	106.3 (2)
N9—C9A—C3A	127.78 (16)	F82—C80—F81	106.12 (18)
N1—C9A—C3A	106.07 (16)	F83—C80—C8	112.35 (18)
C12—C11—C16	121.0 (2)	F82—C80—C8	112.9 (2)
C12—C11—N1	120.6 (2)	F81—C80—C8	112.6 (2)
C16—C11—N1	118.3 (2)	C80—F81—N9	73.15 (13)
C11—C12—C13	119.4 (2)	C80—F82—N9	74.18 (13)
C11—C12—H12	120.3
C9A—N1—N2—C3	0.0 (3)	N2—N1—C9A—C3A	0.0 (3)
C11—N1—N2—C3	179.2 (3)	C11—N1—C9A—C3A	−179.2 (3)
N1—N2—C3—C3A	0.1 (3)	C4—C3A—C9A—N9	0.7 (4)
N1—N2—C3—C31	178.3 (2)	C3—C3A—C9A—N9	178.4 (3)
N2—C3—C3A—C4	176.8 (3)	C4—C3A—C9A—N1	−177.6 (2)
C31—C3—C3A—C4	−1.2 (6)	C3—C3A—C9A—N1	0.1 (3)
N2—C3—C3A—C9A	−0.1 (3)	C9A—N1—C11—C12	29.2 (4)
C31—C3—C3A—C9A	−178.1 (3)	N2—N1—C11—C12	−149.9 (3)
C9A—C3A—C4—C4A	−0.8 (4)	C9A—N1—C11—C16	−153.3 (3)
C3—C3A—C4—C4A	−177.5 (3)	N2—N1—C11—C16	27.6 (4)
C3A—C4—C4A—C5	−179.4 (3)	C16—C11—C12—C13	−0.9 (4)
C3A—C4—C4A—C8A	0.6 (4)	N1—C11—C12—C13	176.5 (3)
C4—C4A—C5—C6	−179.4 (3)	C11—C12—C13—C14	−0.3 (5)
C8A—C4A—C5—C6	0.6 (5)	C12—C13—C14—C15	1.4 (6)
C4A—C5—C6—C7	−0.9 (5)	C13—C14—C15—C16	−1.2 (6)
C5—C6—C7—C8	0.3 (5)	C12—C11—C16—C15	1.1 (4)
C6—C7—C8—C8A	0.5 (5)	N1—C11—C16—C15	−176.3 (3)
C6—C7—C8—C80	−178.5 (3)	C14—C15—C16—C11	0.0 (5)
C7—C8—C8A—N9	179.6 (3)	N2—C3—C31—C36	157.4 (3)
C80—C8—C8A—N9	−1.4 (4)	C3A—C3—C31—C36	−24.7 (4)
C7—C8—C8A—C4A	−0.7 (4)	N2—C3—C31—C32	−23.9 (4)
C80—C8—C8A—C4A	178.3 (3)	C3A—C3—C31—C32	153.9 (3)
C4—C4A—C8A—N9	−0.2 (4)	C36—C31—C32—C33	−0.3 (4)
C5—C4A—C8A—N9	179.8 (3)	C3—C31—C32—C33	−179.0 (3)
C4—C4A—C8A—C8	−179.9 (3)	C31—C32—C33—C34	0.6 (5)
C5—C4A—C8A—C8	0.1 (4)	C32—C33—C34—C35	−0.5 (5)
C8—C8A—N9—C9A	179.7 (2)	C33—C34—C35—C36	0.1 (6)
C4A—C8A—N9—C9A	0.1 (4)	C32—C31—C36—C35	−0.1 (5)
C8—C8A—N9—C80	0.7 (2)	C3—C31—C36—C35	178.5 (3)
C4A—C8A—N9—C80	−178.9 (3)	C34—C35—C36—C31	0.2 (6)
C8—C8A—N9—F82	−21.1 (2)	C7—C8—C80—F83	−1.4 (4)
C4A—C8A—N9—F82	159.3 (2)	C8A—C8—C80—F83	179.6 (3)
C8—C8A—N9—F81	23.3 (2)	C7—C8—C80—F82	−121.3 (3)
C4A—C8A—N9—F81	−156.3 (2)	C8A—C8—C80—F82	59.7 (3)
C8A—N9—C9A—N1	177.7 (2)	C7—C8—C80—F81	118.6 (3)
C8A—N9—C9A—C3A	−0.3 (4)	C8A—C8—C80—F81	−60.4 (3)
N2—N1—C9A—N9	−178.4 (3)	C7—C8—C80—N9	179.7 (3)
C11—N1—C9A—N9	2.4 (5)	C8A—C8—C80—N9	0.68 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N9	0.93	2.50	3.042 (3)	118
C7—H7···F83	0.93	2.35	2.692 (3)	102
C36—H36···F82i	0.93	2.56	3.357 (3)	144
C13—H13···Cg4ii	0.93	2.92	3.729 (4)	146
C33—H33···Cg4iii	0.93	3.03	3.697 (4)	130