Crystal structure of (2-hy­droxy-5-methyl­phen­yl)(3-methyl-1-phenyl-1H-pyrazolo­[3,4-b]pyridin-5-yl)methanone

Raja, R.; Poomathi, N.; Perumal, P.T.; SubbiahPandi, A.

doi:10.1107/S2056989015011597

organic compounds

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Volume 71| Part 7| July 2015| Pages o501-o502

doi:10.1107/S2056989015011597

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Crystal structure of (2-hydroxy-5-methylphenyl)(3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methanone

Rajamani Raja,^a Nataraj Poomathi,^b Paramasivam T. Perumal ^b and A. SubbiahPandi ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bOrganic Chemistry Division, CSIR Central Leather Research Institute, Adyar, Chennai 600 020, India
^*Correspondence e-mail: aspandian59@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 11 June 2015; accepted 15 June 2015; online 24 June 2015)

In the title compound, C₂₁H₁₇N₃O₂, the 2-hydroxy-5-methylphenyl ring and the phenyl ring are inclined to the mean plane of the pyrazolopyridine moiety (r.m.s. deviation = 0.013 Å) by 52.89 (9) and 19.63 (8)°, respectively, and to each other by 42.83 (11)°. In the molecule, there are intramolecular O—H⋯O and C—H⋯N hydrogen bonds, both enclosing an S(6) ring motif. In the crystal, molecules stack along the c-axis direction, forming columns within which there are a number of π–π interactions [the inter-centroid distances vary from 3.5278 (10) to 3.8625 (10) Å]. The columns are linked by C—H⋯π interactions, forming slabs parallel to (100).

Keywords: crystal structure; pyrazoles; propenones; pyrazolopyridine; intramolecular hydrogen bonding; π–π interactions; C—H⋯π interactions.

CCDC reference: 1406889

1. Related literature

For some details of the biological activity of pyrazole derivatives, see: Burger & Iorio (1979 , 1980 ); Kalluraya & Ramesh (2001 ); Windholz (2003 ). For the antibacterial activity of propenones, see: Holla et al. (1994 ). For details of the pyrazole moiety found in blockbuster drugs, see: Penning et al. (1997 ) for celecobix; Terrett et al. (1996 ) for sildenafil; Seltzman et al. (1995 ) for rimonabant.

2. Experimental

2.1. Crystal data

C₂₁H₁₇N₃O₂
M_r = 343.38
Monoclinic, P 2₁ /c
a = 14.7164 (7) Å
b = 16.7306 (9) Å
c = 7.0733 (3) Å
β = 94.857 (2)°
V = 1735.29 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.979, T_max = 0.983
10536 measured reflections
3055 independent reflections
2001 reflections with I > 2σ(I)
R_int = 0.036

2.3. Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.125
S = 1.04
3055 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of rings C1–C4/C6/C7 and C16–C21, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.91	2.613 (2)	143
C21—H21⋯N1	0.93	2.41	3.019 (3)	123
C5—H5A⋯Cg3ⁱ	0.96	2.97	3.703 (3)	134
C20—H20⋯Cg4ⁱ	0.93	2.80	3.608 (2)	146
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1406889

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015011597/su5154sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011597/su5154Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011597/su5154Isup3.cml

checkCIF report

Comments top

Pyrazole derivatives are reported to possess varied biological activities such as anti-inflammatory (Windholz, 2003), analgesic (Windholz, 2003), hypoglysemic, seditive (Burger et al., 1979), hypnotic (Burger et al., 1980), antifungal and antibacterial (Kalluraya & Ramesh, 2001) activities. Propenones are also found to show good antibacterial activity (Holla et al., 1994). The pyrazole moiety is found in blockbuster drugs such as celecobix (Penning et al., 1997), sildenafil (Terrett et al., 1996) and rimonabant (Seltzmann et al., 1995).

The molecular structure of the title molecule is shown in Fig. 1. The 2-hydroxy-5-methylphenyl ring (C1—C4/C6/C7) and the phenyl ring (C16—C21) are inclined to the mean plane of the pyrazolopyridine moiety (N1—N3/C9—C14; r.m.s. deviation = 0.013 Å) by 52.89 (9) and 19.63 (8) °, respectively, and to each other by 42.83 (11) °. The molecular conformation is partly determined by the intramolecular O—H···O hydrogen bond with an S(6) ring motif, and a C—H···N short contact enclosing a second S(6) ring motif (Table 1 and Fig. 1).

In the crystal, the molecules stack along the c axis direction forming columns, within which there are a number of π–π interactions [Cg1···Cg1ⁱ = 3.7660 (10) Å, interplanar distance = 3.4748 (7) Å, slippage = 1.452 Å; Cg1··· Cg1ⁱⁱ = 3.5278 (10) Å, interplanar distance = 3.4477 (7) Å, slippage = 0.747 Å; Cg1···Cg2ⁱ = 3.6162 (10) Å; Cg1···Cg2ⁱⁱ = 3.8625 (10) Å; Cg1 and Cg2 are the centroids of rings N2/N3/C11—C14 and N1/C9—C13, respectively; symmetry codes: (i) -x + 1, -y, -z; (ii) -x + 1, -y, -z + 1]. The columns are linked by C—H···π interactions (Table 1 and Fig. 2) forming slabs parallel to (100).

Synthesis and crystallization top

To a mixture of 3-formylchromone and 5-amino-3-methyl-1-phenyl pyrazole in ethanol, was added a catalytic amount of In(OTf)₃ and the resulting mixture was refluxed for ca. 20 min. The precipitate formed was filtered and dried under vacuum to afford the pure title product (yield: 87%). It was recrystallized from ethanol and DMSO-D₆ by slow evaporation over 48 h, giving colourless block-like crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The O- and C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms: O—H = 0.82 Å, C–H = 0.93–0.96 Å with U_iso(H) = 1.5U_eq(O,C) for the hydroxyl and methyl H atoms and 1.2U_eq(C) for other H atoms.

Related literature top

For some details of the biological activity of pyrazole derivatives, see: Burger & Iorio (1979, 1980); Kalluraya & Ramesh (2001); Windholz (2003). For the antibacterial activity of propenones, see: Holla et al. (1994). For details of the pyrazole moiety found in blockbuster drugs, see: Penning et al. (1997) for celecobix; Terrett et al. (1996) for sildenafil; Seltzman et al. (1995) for rimonabant.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Intramolecular hydrogen bonds are shown as dashed lines (see Table 1 for details)
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. The O—H···O and C—H···π interactions are shown as dashed lines (see Table 1 for details).

(2-Hydroxy-5-methylphenyl)(3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methanone top

Crystal data top

C₂₁H₁₇N₃O₂	F(000) = 720
M_r = 343.38	D_x = 1.314 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2001 reflections
a = 14.7164 (7) Å	θ = 1.4–25.0°
b = 16.7306 (9) Å	µ = 0.09 mm⁻¹
c = 7.0733 (3) Å	T = 293 K
β = 94.857 (2)°	Block, colourless
V = 1735.29 (14) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3055 independent reflections
Radiation source: fine-focus sealed tube	2001 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω and ϕ scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
T_min = 0.979, T_max = 0.983	k = −19→19
10536 measured reflections	l = −5→8

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0597P)² + 0.1547P] where P = (F_o² + 2F_c²)/3
3055 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₁₇N₃O₂	V = 1735.29 (14) Å³
M_r = 343.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.7164 (7) Å	µ = 0.09 mm⁻¹
b = 16.7306 (9) Å	T = 293 K
c = 7.0733 (3) Å	0.25 × 0.20 × 0.20 mm
β = 94.857 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3055 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2001 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.036
10536 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
3055 reflections	Δρ_min = −0.18 e Å⁻³
237 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.05588 (15)	0.09390 (16)	0.0431 (4)	0.0621 (7)
C2	0.00532 (16)	0.13878 (17)	−0.0938 (4)	0.0746 (8)
H2	−0.0552	0.1509	−0.0781	0.090*
C3	0.04416 (17)	0.16526 (16)	−0.2520 (4)	0.0724 (8)
H3	0.0090	0.1950	−0.3420	0.087*
C4	0.13449 (15)	0.14903 (14)	−0.2816 (3)	0.0559 (6)
C5	0.17618 (19)	0.17799 (17)	−0.4560 (4)	0.0787 (8)
H5A	0.1872	0.2344	−0.4458	0.118*
H5B	0.1352	0.1674	−0.5660	0.118*
H5C	0.2328	0.1506	−0.4675	0.118*
C6	0.18475 (14)	0.10574 (13)	−0.1436 (3)	0.0491 (6)
H6	0.2454	0.0945	−0.1602	0.059*
C7	0.14798 (13)	0.07811 (13)	0.0206 (3)	0.0482 (6)
C8	0.20198 (14)	0.03024 (15)	0.1632 (3)	0.0517 (6)
C9	0.30348 (13)	0.03373 (13)	0.1803 (3)	0.0420 (5)
C10	0.35019 (13)	0.10607 (14)	0.1603 (3)	0.0451 (5)
H10	0.3150	0.1511	0.1289	0.054*
C11	0.48557 (12)	0.04804 (12)	0.2241 (2)	0.0358 (5)
C12	0.44789 (12)	−0.02748 (12)	0.2511 (2)	0.0364 (5)
C13	0.35323 (13)	−0.03413 (13)	0.2305 (3)	0.0426 (5)
H13	0.3245	−0.0826	0.2500	0.051*
C14	0.52392 (13)	−0.07907 (13)	0.2957 (3)	0.0409 (5)
C15	0.52419 (16)	−0.16642 (14)	0.3369 (3)	0.0585 (6)
H15A	0.5858	−0.1858	0.3471	0.088*
H15B	0.4895	−0.1940	0.2360	0.088*
H15C	0.4975	−0.1757	0.4542	0.088*
C16	0.64979 (12)	0.09625 (12)	0.2357 (2)	0.0376 (5)
C17	0.73654 (13)	0.07915 (14)	0.3181 (3)	0.0484 (6)
H17	0.7475	0.0326	0.3881	0.058*
C18	0.80646 (14)	0.13251 (17)	0.2945 (3)	0.0618 (7)
H18	0.8650	0.1211	0.3478	0.074*
C19	0.79085 (16)	0.20215 (17)	0.1933 (3)	0.0639 (7)
H19	0.8384	0.2375	0.1783	0.077*
C20	0.70447 (15)	0.21893 (15)	0.1146 (3)	0.0548 (6)
H20	0.6935	0.2662	0.0473	0.066*
C21	0.63382 (14)	0.16638 (13)	0.1345 (3)	0.0448 (5)
H21	0.5756	0.1780	0.0800	0.054*
N1	0.44001 (10)	0.11614 (10)	0.1820 (2)	0.0426 (4)
N2	0.57850 (10)	0.03981 (10)	0.2511 (2)	0.0378 (4)
N3	0.60079 (11)	−0.03890 (10)	0.2955 (2)	0.0421 (4)
O1	0.01363 (10)	0.06702 (12)	0.1927 (3)	0.0870 (6)
H1	0.0497	0.0411	0.2629	0.130*
O2	0.16431 (10)	−0.01281 (12)	0.2757 (2)	0.0770 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0363 (13)	0.0691 (19)	0.0801 (16)	−0.0013 (12)	0.0012 (12)	−0.0142 (14)
C2	0.0360 (13)	0.078 (2)	0.108 (2)	0.0116 (13)	−0.0070 (14)	−0.0114 (17)
C3	0.0540 (16)	0.0674 (19)	0.0910 (19)	0.0122 (14)	−0.0217 (14)	−0.0046 (16)
C4	0.0514 (14)	0.0499 (16)	0.0636 (14)	0.0071 (12)	−0.0111 (11)	−0.0101 (12)
C5	0.0879 (19)	0.076 (2)	0.0695 (16)	0.0080 (16)	−0.0083 (14)	0.0057 (14)
C6	0.0362 (11)	0.0506 (15)	0.0591 (13)	0.0039 (10)	−0.0035 (10)	−0.0120 (11)
C7	0.0296 (11)	0.0521 (15)	0.0622 (13)	0.0028 (10)	−0.0007 (10)	−0.0120 (11)
C8	0.0384 (12)	0.0626 (17)	0.0542 (13)	−0.0040 (11)	0.0044 (10)	−0.0059 (12)
C9	0.0336 (11)	0.0484 (14)	0.0438 (11)	0.0006 (10)	0.0012 (8)	−0.0025 (10)
C10	0.0368 (12)	0.0459 (14)	0.0516 (12)	0.0073 (10)	−0.0020 (9)	−0.0009 (10)
C11	0.0317 (10)	0.0394 (13)	0.0361 (10)	0.0031 (9)	0.0016 (8)	−0.0025 (9)
C12	0.0366 (11)	0.0377 (13)	0.0348 (9)	0.0001 (9)	0.0025 (8)	−0.0048 (9)
C13	0.0425 (12)	0.0451 (14)	0.0407 (10)	−0.0082 (10)	0.0062 (9)	−0.0048 (9)
C14	0.0447 (12)	0.0382 (13)	0.0396 (10)	0.0015 (10)	0.0030 (9)	−0.0029 (9)
C15	0.0648 (15)	0.0400 (15)	0.0693 (14)	0.0025 (12)	−0.0020 (12)	0.0037 (11)
C16	0.0337 (11)	0.0435 (14)	0.0363 (10)	−0.0009 (9)	0.0071 (8)	−0.0068 (9)
C17	0.0373 (12)	0.0518 (15)	0.0558 (12)	0.0066 (11)	0.0023 (9)	−0.0054 (11)
C18	0.0319 (12)	0.076 (2)	0.0775 (16)	−0.0011 (12)	0.0064 (11)	−0.0127 (15)
C19	0.0485 (15)	0.072 (2)	0.0747 (16)	−0.0190 (13)	0.0219 (12)	−0.0100 (14)
C20	0.0579 (15)	0.0539 (16)	0.0541 (12)	−0.0116 (12)	0.0134 (11)	0.0017 (11)
C21	0.0432 (12)	0.0477 (15)	0.0432 (11)	−0.0032 (10)	0.0026 (9)	0.0001 (10)
N1	0.0340 (9)	0.0412 (11)	0.0520 (10)	0.0031 (8)	0.0003 (7)	−0.0012 (8)
N2	0.0324 (9)	0.0364 (11)	0.0443 (9)	0.0032 (8)	0.0013 (7)	0.0005 (8)
N3	0.0403 (10)	0.0367 (11)	0.0490 (9)	0.0066 (8)	0.0020 (7)	0.0006 (8)
O1	0.0393 (10)	0.1199 (18)	0.1043 (14)	−0.0003 (10)	0.0207 (9)	0.0018 (12)
O2	0.0431 (9)	0.1069 (16)	0.0816 (11)	−0.0112 (10)	0.0087 (8)	0.0238 (11)

Geometric parameters (Å, º) top

C1—O1	1.349 (3)	C11—C12	1.399 (3)
C1—C2	1.391 (3)	C12—C13	1.393 (3)
C1—C7	1.403 (3)	C12—C14	1.427 (3)
C2—C3	1.372 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—N3	1.316 (2)
C3—C4	1.390 (3)	C14—C15	1.490 (3)
C3—H3	0.9300	C15—H15A	0.9600
C4—C6	1.379 (3)	C15—H15B	0.9600
C4—C5	1.504 (3)	C15—H15C	0.9600
C5—H5A	0.9600	C16—C21	1.384 (3)
C5—H5B	0.9600	C16—C17	1.388 (3)
C5—H5C	0.9600	C16—N2	1.423 (2)
C6—C7	1.401 (3)	C17—C18	1.383 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.468 (3)	C18—C19	1.376 (3)
C8—O2	1.239 (3)	C18—H18	0.9300
C8—C9	1.489 (3)	C19—C20	1.373 (3)
C9—C13	1.381 (3)	C19—H19	0.9300
C9—C10	1.405 (3)	C20—C21	1.378 (3)
C10—N1	1.328 (2)	C20—H20	0.9300
C10—H10	0.9300	C21—H21	0.9300
C11—N1	1.343 (2)	N2—N3	1.387 (2)
C11—N2	1.372 (2)	O1—H1	0.8200

O1—C1—C2	118.1 (2)	C11—C12—C14	105.31 (17)
O1—C1—C7	122.7 (2)	C9—C13—C12	117.71 (19)
C2—C1—C7	119.2 (2)	C9—C13—H13	121.1
C3—C2—C1	120.5 (2)	C12—C13—H13	121.1
C3—C2—H2	119.8	N3—C14—C12	110.41 (18)
C1—C2—H2	119.8	N3—C14—C15	120.87 (19)
C2—C3—C4	122.0 (2)	C12—C14—C15	128.72 (19)
C2—C3—H3	119.0	C14—C15—H15A	109.5
C4—C3—H3	119.0	C14—C15—H15B	109.5
C6—C4—C3	117.3 (2)	H15A—C15—H15B	109.5
C6—C4—C5	121.2 (2)	C14—C15—H15C	109.5
C3—C4—C5	121.5 (2)	H15A—C15—H15C	109.5
C4—C5—H5A	109.5	H15B—C15—H15C	109.5
C4—C5—H5B	109.5	C21—C16—C17	120.13 (19)
H5A—C5—H5B	109.5	C21—C16—N2	120.56 (16)
C4—C5—H5C	109.5	C17—C16—N2	119.28 (18)
H5A—C5—H5C	109.5	C18—C17—C16	118.9 (2)
H5B—C5—H5C	109.5	C18—C17—H17	120.5
C4—C6—C7	122.6 (2)	C16—C17—H17	120.5
C4—C6—H6	118.7	C19—C18—C17	121.1 (2)
C7—C6—H6	118.7	C19—C18—H18	119.5
C6—C7—C1	118.5 (2)	C17—C18—H18	119.5
C6—C7—C8	121.67 (18)	C20—C19—C18	119.5 (2)
C1—C7—C8	119.8 (2)	C20—C19—H19	120.3
O2—C8—C7	120.86 (19)	C18—C19—H19	120.3
O2—C8—C9	118.09 (19)	C19—C20—C21	120.6 (2)
C7—C8—C9	121.03 (19)	C19—C20—H20	119.7
C13—C9—C10	118.74 (18)	C21—C20—H20	119.7
C13—C9—C8	119.7 (2)	C20—C21—C16	119.81 (19)
C10—C9—C8	121.43 (19)	C20—C21—H21	120.1
N1—C10—C9	126.03 (19)	C16—C21—H21	120.1
N1—C10—H10	117.0	C10—N1—C11	113.03 (18)
C9—C10—H10	117.0	C11—N2—N3	109.93 (16)
N1—C11—N2	126.11 (18)	C11—N2—C16	130.97 (17)
N1—C11—C12	126.89 (17)	N3—N2—C16	119.08 (15)
N2—C11—C12	107.00 (17)	C14—N3—N2	107.36 (15)
C13—C12—C11	117.53 (18)	C1—O1—H1	109.5
C13—C12—C14	137.2 (2)

O1—C1—C2—C3	−177.8 (2)	C11—C12—C13—C9	1.6 (2)
C7—C1—C2—C3	2.0 (4)	C14—C12—C13—C9	−178.63 (19)
C1—C2—C3—C4	−0.3 (4)	C13—C12—C14—N3	−179.9 (2)
C2—C3—C4—C6	−0.9 (4)	C11—C12—C14—N3	−0.1 (2)
C2—C3—C4—C5	179.7 (2)	C13—C12—C14—C15	0.7 (4)
C3—C4—C6—C7	0.3 (3)	C11—C12—C14—C15	−179.57 (19)
C5—C4—C6—C7	179.8 (2)	C21—C16—C17—C18	−1.1 (3)
C4—C6—C7—C1	1.3 (3)	N2—C16—C17—C18	176.83 (17)
C4—C6—C7—C8	178.3 (2)	C16—C17—C18—C19	0.9 (3)
O1—C1—C7—C6	177.3 (2)	C17—C18—C19—C20	0.0 (4)
C2—C1—C7—C6	−2.4 (3)	C18—C19—C20—C21	−0.7 (3)
O1—C1—C7—C8	0.3 (4)	C19—C20—C21—C16	0.4 (3)
C2—C1—C7—C8	−179.5 (2)	C17—C16—C21—C20	0.5 (3)
C6—C7—C8—O2	−158.7 (2)	N2—C16—C21—C20	−177.45 (17)
C1—C7—C8—O2	18.2 (3)	C9—C10—N1—C11	1.0 (3)
C6—C7—C8—C9	23.0 (3)	N2—C11—N1—C10	178.78 (16)
C1—C7—C8—C9	−160.0 (2)	C12—C11—N1—C10	−2.1 (3)
O2—C8—C9—C13	36.0 (3)	N1—C11—N2—N3	178.98 (17)
C7—C8—C9—C13	−145.7 (2)	C12—C11—N2—N3	−0.31 (19)
O2—C8—C9—C10	−139.2 (2)	N1—C11—N2—C16	−2.9 (3)
C7—C8—C9—C10	39.1 (3)	C12—C11—N2—C16	177.79 (16)
C13—C9—C10—N1	1.3 (3)	C21—C16—N2—C11	−19.2 (3)
C8—C9—C10—N1	176.53 (18)	C17—C16—N2—C11	162.90 (18)
N1—C11—C12—C13	0.8 (3)	C21—C16—N2—N3	158.80 (17)
N2—C11—C12—C13	−179.92 (15)	C17—C16—N2—N3	−19.1 (2)
N1—C11—C12—C14	−179.01 (17)	C12—C14—N3—N2	0.0 (2)
N2—C11—C12—C14	0.27 (19)	C15—C14—N3—N2	179.44 (17)
C10—C9—C13—C12	−2.6 (3)	C11—N2—N3—C14	0.23 (19)
C8—C9—C13—C12	−177.90 (16)	C16—N2—N3—C14	−178.13 (14)

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of rings C1–C4/C6/C7 and C16–C21, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.91	2.613 (2)	143
C21—H21···N1	0.93	2.41	3.019 (3)	123
C5—H5A···Cg3ⁱ	0.96	2.97	3.703 (3)	134
C20—H20···Cg4ⁱ	0.93	2.80	3.608 (2)	146

Symmetry code: (i) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of rings C1–C4/C6/C7 and C16–C21, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.91	2.613 (2)	143
C21—H21···N1	0.93	2.41	3.019 (3)	123
C5—H5A···Cg3ⁱ	0.96	2.97	3.703 (3)	134
C20—H20···Cg4ⁱ	0.93	2.80	3.608 (2)	146

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The authors thank the Department of Chemistry, IIT, Chennai, India, for the X-ray intensity data collection.

References

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Volume 71| Part 7| July 2015| Pages o501-o502

doi:10.1107/S2056989015011597

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (2-hy­dr­oxy-5-methyl­phen­yl)(3-methyl-1-phenyl-1H-pyrazolo­[3,4-b]pyridin-5-yl)methanone

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (2-hydroxy-5-methylphenyl)(3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methanone