3,4,6-Trimethyl-1-phenyl-1H-pyrazolo-[3,4-b]pyridine.

In the title compound, C(15)H(15)N(3), the 1H-pyrazolo-[3,4-b]pyridine system and the phenyl ring are each individually planar, with r.m.s. deviations of 0.017 (2) and 0.011 (2) Å, respectively; the dihedral angle between the two aromatic systems is 9.33 (10)°. The crystal packing is stabilized by offset π-π stacking between parallel pyrazolo-[3,4-b]pyridine ring systems [face-to-face distance = 3.449 (6) Å].

Related literature

For a general review of pyrazolo­pyridines, see: Hardy (1984 ▶). For related compounds displaying biological activity, see: Chu & Lynchj (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H15N3

M = 237.30

Monoclinic,

a = 7.1714 (2) Å

b = 12.0690 (4) Å

c = 14.5491 (5) Å

β = 101.251 (1)°

V = 1235.05 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.32 × 0.29 × 0.12 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

10642 measured reflections

2252 independent reflections

1841 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.198

S = 1.09

2252 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810026474/xu2793sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026474/xu2793Isup2.hkl

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

C15H15N3	F(000) = 504
Mr = 237.30	Dx = 1.276 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1348 reflections
a = 7.1714 (2) Å	θ = 2.6–25.5°
b = 12.0690 (4) Å	µ = 0.08 mm−1
c = 14.5491 (5) Å	T = 296 K
β = 101.251 (1)°	Prism, colourless
V = 1235.05 (7) Å3	0.32 × 0.29 × 0.12 mm
Z = 4

Bruker X8 APEXII CCD area-detector diffractometer	1841 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 25.3°, θmin = 2.9°
φ and ω scans	h = −7→8
10642 measured reflections	k = −14→14
2252 independent reflections	l = −17→17

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.104P)2 + 1.0638P] where P = (Fo2 + 2Fc2)/3
2252 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) 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. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
C1	0.8454 (3)	0.7445 (2)	−0.04712 (18)	0.0367 (6)
C2	0.7992 (4)	0.6928 (2)	−0.13595 (19)	0.0421 (7)
C3	0.7465 (3)	0.5818 (2)	−0.14607 (17)	0.0332 (6)
C4	0.7468 (3)	0.5266 (2)	−0.06073 (18)	0.0351 (6)
C5	0.7917 (3)	0.5850 (2)	0.02285 (17)	0.0316 (6)
C6	0.9021 (4)	0.8635 (2)	−0.0425 (2)	0.0472 (7)
C7	0.6952 (4)	0.5279 (3)	−0.23948 (19)	0.0492 (8)
C8	0.7099 (3)	0.4171 (2)	−0.0326 (2)	0.0380 (7)
C9	0.6593 (4)	0.3137 (3)	−0.0909 (2)	0.0481 (8)
C10	0.8125 (3)	0.5303 (2)	0.19304 (17)	0.0317 (6)
C11	0.8164 (3)	0.4380 (2)	0.24944 (19)	0.0378 (6)
C12	0.8416 (4)	0.4501 (2)	0.3447 (2)	0.0404 (7)
C13	0.8649 (4)	0.5527 (2)	0.38535 (18)	0.0362 (6)
C14	0.8657 (4)	0.6457 (2)	0.33032 (18)	0.0356 (6)
C15	0.8396 (3)	0.6356 (2)	0.23326 (18)	0.0355 (6)
N1	0.8420 (3)	0.69504 (17)	0.03365 (15)	0.0339 (5)
N2	0.7298 (3)	0.41044 (18)	0.05772 (16)	0.0380 (6)
N3	0.7801 (3)	0.51439 (17)	0.09427 (15)	0.0332 (5)
H11	0.8019	0.3677	0.2228	0.045*
H12	0.8428	0.3877	0.3823	0.048*
H13	0.8802	0.5597	0.4501	0.043*
H14	0.8838	0.7153	0.3581	0.043*
H15	0.8401	0.6980	0.1958	0.043*
H2	0.8042	0.7343	−0.1893	0.051*
H6A	0.7931	0.9085	−0.0665	0.071*
H6B	0.9975	0.8750	−0.0796	0.071*
H6C	0.9523	0.8835	0.0214	0.071*
H7A	0.7068	0.5806	−0.2874	0.074*
H7B	0.5666	0.5016	−0.2488	0.074*
H7C	0.7792	0.4666	−0.2425	0.074*
H9A	0.7662	0.2913	−0.1173	0.072*
H9B	0.5529	0.3288	−0.1405	0.072*
H9C	0.6268	0.2554	−0.0520	0.072*

	U11	U22	U33	U12	U13	U23
C1	0.0326 (13)	0.0418 (15)	0.0371 (14)	0.0062 (11)	0.0100 (11)	−0.0020 (11)
C2	0.0459 (15)	0.0491 (17)	0.0334 (15)	0.0081 (12)	0.0129 (12)	0.0066 (12)
C3	0.0279 (12)	0.0443 (15)	0.0284 (13)	0.0109 (10)	0.0075 (10)	0.0000 (11)
C4	0.0274 (12)	0.0418 (15)	0.0358 (14)	0.0058 (10)	0.0055 (10)	−0.0037 (11)
C5	0.0251 (11)	0.0406 (14)	0.0302 (13)	0.0069 (10)	0.0082 (9)	0.0044 (10)
C6	0.0545 (17)	0.0469 (17)	0.0440 (17)	0.0002 (13)	0.0191 (13)	0.0156 (13)
C7	0.0453 (16)	0.068 (2)	0.0342 (15)	0.0045 (14)	0.0065 (12)	−0.0091 (14)
C8	0.0257 (12)	0.0334 (14)	0.0554 (18)	0.0045 (10)	0.0092 (11)	0.0069 (12)
C9	0.0431 (15)	0.0554 (19)	0.0420 (17)	0.0041 (13)	−0.0011 (12)	−0.0138 (13)
C10	0.0224 (11)	0.0444 (15)	0.0279 (12)	0.0048 (10)	0.0041 (9)	−0.0043 (11)
C11	0.0367 (13)	0.0302 (13)	0.0470 (16)	−0.0026 (10)	0.0096 (11)	−0.0034 (11)
C12	0.0430 (14)	0.0353 (15)	0.0445 (16)	0.0020 (11)	0.0127 (12)	0.0116 (12)
C13	0.0400 (14)	0.0445 (15)	0.0238 (12)	0.0081 (11)	0.0050 (10)	0.0046 (11)
C14	0.0422 (14)	0.0296 (13)	0.0338 (14)	0.0040 (11)	0.0044 (11)	−0.0049 (10)
C15	0.0394 (13)	0.0338 (13)	0.0333 (14)	0.0079 (11)	0.0072 (10)	0.0114 (11)
N1	0.0322 (11)	0.0275 (11)	0.0444 (13)	0.0041 (8)	0.0134 (9)	0.0057 (9)
N2	0.0374 (12)	0.0295 (12)	0.0460 (14)	−0.0025 (9)	0.0053 (10)	−0.0084 (10)
N3	0.0373 (11)	0.0284 (11)	0.0339 (12)	−0.0010 (9)	0.0068 (9)	−0.0026 (9)

C1—C6	1.491 (4)	C10—C11	1.380 (4)
C2—H2	0.9300	C11—H11	0.9300
C2—C1	1.415 (4)	C11—C12	1.370 (4)
C3—C7	1.487 (4)	C12—H12	0.9300
C3—C4	1.408 (4)	C13—H13	0.9300
C3—C2	1.392 (4)	C13—C14	1.379 (4)
C4—C8	1.424 (4)	C13—C12	1.368 (4)
C4—C5	1.388 (4)	C14—H14	0.9300
C6—H6C	0.9600	C15—H15	0.9300
C6—H6B	0.9600	C15—C10	1.397 (4)
C6—H6A	0.9600	C15—C14	1.393 (4)
C7—H7C	0.9600	N1—C5	1.377 (3)
C7—H7B	0.9600	N1—C1	1.322 (3)
C7—H7A	0.9600	N2—N3	1.383 (3)
C8—C9	1.512 (4)	N2—C8	1.296 (4)
C9—H9C	0.9600	N3—C10	1.423 (3)
C9—H9B	0.9600	N3—C5	1.359 (3)
C9—H9A	0.9600
C1—C6—H6C	109.5	C12—C13—C14	119.9 (2)
C1—C6—H6B	109.5	C12—C11—H11	120.0
C1—C6—H6A	109.5	C12—C11—C10	119.9 (2)
C1—C2—H2	118.9	C13—C12—H12	119.5
C1—N1—C5	112.6 (2)	C13—C12—C11	121.0 (2)
C2—C1—C6	118.6 (2)	C13—C14—H14	119.9
C2—C3—C7	122.1 (2)	C13—C14—C15	120.2 (2)
C2—C3—C4	114.1 (2)	C14—C13—H13	120.0
C3—C7—H7C	109.5	C14—C15—H15	120.5
C3—C7—H7B	109.5	C14—C15—C10	119.0 (2)
C3—C7—H7A	109.5	C15—C14—H14	119.9
C3—C2—H2	118.9	C15—C10—N3	121.8 (2)
C3—C2—C1	122.1 (2)	H6A—C6—H6C	109.5
C3—C4—C8	136.4 (3)	H6A—C6—H6B	109.5
C4—C8—C9	130.0 (3)	H6B—C6—H6C	109.5
C4—C3—C7	123.8 (3)	H7A—C7—H7C	109.5
C5—C4—C8	104.1 (2)	H7A—C7—H7B	109.5
C5—C4—C3	119.5 (3)	H7B—C7—H7C	109.5
C5—N3—C10	131.7 (2)	H9A—C9—H9C	109.5
C5—N3—N2	109.0 (2)	H9A—C9—H9B	109.5
C8—C9—H9C	109.5	H9B—C9—H9C	109.5
C8—C9—H9B	109.5	N1—C1—C6	116.6 (2)
C8—C9—H9A	109.5	N1—C1—C2	124.8 (3)
C8—N2—N3	107.6 (2)	N1—C5—C4	126.9 (2)
C10—C11—H11	120.0	N2—C8—C9	119.0 (2)
C10—C15—H15	120.5	N2—C8—C4	111.0 (2)
C11—C12—H12	119.5	N2—N3—C10	119.3 (2)
C11—C10—N3	118.2 (2)	N3—C5—C4	108.2 (2)
C11—C10—C15	120.0 (2)	N3—C5—N1	124.8 (2)
C12—C13—H13	120.0