Ethyl 3-{5-[(diethyl­amino)meth­yl]isoxazol-3-yl}-2-phenyl­pyrazolo[1,5-a]pyridine-5-carboxyl­ate

Meng, Q.-Y.; Jia, J.; Yin, L.; Zhan, F.-X.; Wang, J.-W.

doi:10.1107/S1600536810004174

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o723

doi:10.1107/S1600536810004174

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Ethyl 3-{5-[(diethylamino)methyl]isoxazol-3-yl}-2-phenylpyrazolo[1,5-a]pyridine-5-carboxylate

Qing-Yang Meng,^a Jiong Jia,^a Ling Yin,^a Fu-Xu Zhan ^a and Jian-Wu Wang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: jwwang@sdu.edu.cn

(Received 8 January 2010; accepted 2 February 2010; online 3 March 2010)

In the title compound, C₂₄H₂₆N₄O₃, the pyrazolo[1,5-a]pyridine ring system makes dihedral angles of 38.130 (3) and 30.120 (3)°, respectively, with the isoxazole and phenyl rings. In the crystal, two molecules are linked by a pair of C—H⋯N hydrogen bonds, forming a centrosymmetric dimer. A weak intramolecular C—H⋯O interaction is also present.

Related literature

For the bioactivity of pyrazolo[1,5-a]pyridine and isoxazole derivatives, see: Cuny et al. (2008 ); Ge et al. (2009 ); Johns et al. (2005 ); Lanig et al. (2001 ); Lee et al. (2009 ). For the synthesis of ethyl 3-(5-((methylsulfonyloxy)methyl)isoxazol-3-yl)-2-phenyl-H-pyrazolo[1,5-a]pyridine-5-carboxylate, see: Meng et al. (2010 ).

Experimental

Crystal data

C₂₄H₂₆N₄O₃
M_r = 418.49
Triclinic, $[P \overline 1]$
a = 6.1250 (7) Å
b = 13.1425 (16) Å
c = 13.7139 (16) Å
α = 93.600 (2)°
β = 95.514 (2)°
γ = 95.637 (2)°
V = 1090.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.10 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.992, T_max = 0.992
5453 measured reflections
3800 independent reflections
2842 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.187
S = 1.07
3800 reflections
281 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N2ⁱ	0.93	2.54	3.456 (3)	169
C22—H22A⋯O3	0.97	2.52	3.218 (3)	129
Symmetry code: (i) -x-1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004174/is2515sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004174/is2515Isup2.hkl

checkCIF report

Comment top

Pyrazolo[1,5-a]pyridine derivatives have been intensively investigated due to their widespread biological activities (Cuny et al., 2008; Johns et al., 2005; Lanig et al., 2001). Thus, it is necessary to further widen the system of application of heterocycle compounds. Recently, an interesting intramolecular condensation of α,β-unsaturated esters with aldehydes has been discovered, leading to a series of pyrazolo[1,5-a]pyridines under mild conditions (Ge et al., 2009). Moreover, it is well known that many compounds with isoxazole core show potent antitumor activities (Lee et al., 2009). It is therefore worth trying to incorporate isoxazole core into pyrazolo[1,5-a]pyridine scaffold to improve the biological activity (Meng et al., 2010). Herein, a novel heterocycle compound has been obtained and its molecular structure is depicted (Fig. 1).

Related literature top

For the bioactivity of pyrazolo[1,5-a]pyridine and isoxazole derivatives, see: Cuny et al. (2008); Ge et al. (2009); Johns et al. (2005); Lanig et al. (2001); Lee et al. (2009). For the synthsis of ethyl 3-(5-((methylsulfonyloxy)methyl)isoxazol-3-yl)-2-phenyl H-pyrazolo[1,5-a]pyridine-5-carboxylate, see: Meng et al. (2010).

Experimental top

To a solution of ethyl 3-{5-[(methylsulfonyloxy)methyl]isoxazol-3-yl}-2-phenyl H-pyrazolo[1,5-a]pyridine-5-carboxylate (Meng et al., 2010) (0.33 g, 0.75 mmol) in THF (20 ml) was added diethylamine (0.22 ml, 2.25 mmol). The mixture was stirred for 12 h. Water and dichloromethane were added in turn and stirred, and layers were separated. The aqueous layer was back-extracted with dichloromethane. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (yield 89%). The crystals of (I) were obtained from a hexane-ethyl acetate-dichloromethane (3:1:1, v/v/v) solution by slow evaporation at room temperature (m.p. 363–364 K).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title compound, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Ethyl 3-{5-[(diethylamino)methyl]isoxazol-3-yl}-2- phenylpyrazolo[1,5-a]pyridine-5-carboxylate top

Crystal data top

C₂₄H₂₆N₄O₃	Z = 2
M_r = 418.49	F(000) = 444
Triclinic, P1	D_x = 1.274 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1250 (7) Å	Cell parameters from 1181 reflections
b = 13.1425 (16) Å	θ = 2.5–25.5°
c = 13.7139 (16) Å	µ = 0.09 mm⁻¹
α = 93.600 (2)°	T = 298 K
β = 95.514 (2)°	Block, colorless
γ = 95.637 (2)°	0.10 × 0.10 × 0.10 mm
V = 1090.6 (2) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3800 independent reflections
Radiation source: fine-focus sealed tube	2842 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 1.5°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→13
T_min = 0.992, T_max = 0.992	l = −14→16
5453 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.187	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0993P)² + 0.4336P] where P = (F_o² + 2F_c²)/3
3800 reflections	(Δ/σ)_max = 0.004
281 parameters	Δρ_max = 0.75 e Å⁻³
1 restraint	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₄H₂₆N₄O₃	γ = 95.637 (2)°
M_r = 418.49	V = 1090.6 (2) Å³
Triclinic, P1	Z = 2
a = 6.1250 (7) Å	Mo Kα radiation
b = 13.1425 (16) Å	µ = 0.09 mm⁻¹
c = 13.7139 (16) Å	T = 298 K
α = 93.600 (2)°	0.10 × 0.10 × 0.10 mm
β = 95.514 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3800 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2842 reflections with I > 2σ(I)
T_min = 0.992, T_max = 0.992	R_int = 0.014
5453 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	1 restraint
wR(F²) = 0.187	H-atom parameters constrained
S = 1.07	Δρ_max = 0.75 e Å⁻³
3800 reflections	Δρ_min = −0.35 e Å⁻³
281 parameters

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. 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	0.2802 (5)	−0.0313 (2)	0.0758 (3)	0.0669 (9)
H1A	0.4008	−0.0724	0.0722	0.100*
H1B	0.2200	−0.0200	0.0106	0.100*
H1C	0.1680	−0.0663	0.1094	0.100*
C2	0.3600 (5)	0.0686 (2)	0.1300 (2)	0.0585 (8)
H2A	0.4219	0.0570	0.1957	0.070*
H2B	0.4758	0.1031	0.0968	0.070*
C3	0.1430 (4)	0.19374 (19)	0.06317 (19)	0.0441 (6)
C4	−0.0421 (4)	0.25659 (18)	0.07983 (17)	0.0393 (6)
C5	−0.1456 (4)	0.25212 (18)	0.16402 (17)	0.0366 (5)
H5	−0.1060	0.2073	0.2109	0.044*
C6	−0.3125 (4)	0.31605 (17)	0.17869 (16)	0.0346 (5)
C7	−0.2687 (4)	0.3840 (2)	0.02118 (18)	0.0451 (6)
H7	−0.3130	0.4270	−0.0266	0.054*
C8	−0.1074 (5)	0.3235 (2)	0.00756 (18)	0.0470 (6)
H8	−0.0380	0.3255	−0.0498	0.056*
C9	−0.4470 (4)	0.33567 (17)	0.25335 (16)	0.0358 (5)
C10	−0.5678 (4)	0.41490 (18)	0.22118 (17)	0.0366 (5)
C11	−0.7208 (4)	0.47407 (18)	0.27307 (18)	0.0387 (6)
C12	−0.6795 (5)	0.5013 (2)	0.3729 (2)	0.0556 (7)
H12	−0.5587	0.4790	0.4087	0.067*
C13	−0.8164 (6)	0.5616 (3)	0.4199 (2)	0.0686 (9)
H13	−0.7867	0.5799	0.4868	0.082*
C14	−0.9967 (6)	0.5946 (2)	0.3677 (3)	0.0675 (9)
H14	−1.0897	0.6345	0.3993	0.081*
C15	−1.0381 (5)	0.5682 (2)	0.2687 (3)	0.0610 (8)
H15	−1.1597	0.5904	0.2335	0.073*
C16	−0.9014 (4)	0.50908 (19)	0.2210 (2)	0.0464 (6)
H16	−0.9301	0.4925	0.1538	0.056*
C17	−0.4706 (4)	0.27444 (18)	0.33801 (17)	0.0369 (5)
C18	−0.6611 (4)	0.2496 (2)	0.38597 (18)	0.0437 (6)
H18	−0.7981	0.2739	0.3743	0.052*
C19	−0.6021 (5)	0.1835 (2)	0.45177 (19)	0.0467 (6)
C20	−0.7261 (5)	0.1236 (2)	0.5216 (2)	0.0582 (8)
H20A	−0.8790	0.1091	0.4945	0.070*
H20B	−0.6655	0.0586	0.5283	0.070*
C21	−0.4753 (6)	0.2470 (3)	0.7671 (2)	0.0775 (10)
H21A	−0.3289	0.2451	0.7985	0.116*
H21B	−0.5810	0.2223	0.8097	0.116*
H21C	−0.4972	0.3162	0.7534	0.116*
C22	−0.5053 (6)	0.1792 (3)	0.6711 (2)	0.0719 (9)
H22A	−0.3953	0.2038	0.6293	0.086*
H22B	−0.4793	0.1099	0.6855	0.086*
C23	−0.9023 (6)	0.1347 (3)	0.6722 (3)	0.0747 (10)
H23A	−0.9082	0.1799	0.7304	0.090*
H23B	−1.0389	0.1367	0.6305	0.090*
C24	−0.8942 (7)	0.0293 (3)	0.7027 (3)	0.0898 (12)
H24A	−1.0212	0.0102	0.7361	0.135*
H24B	−0.7628	0.0263	0.7462	0.135*
H24C	−0.8935	−0.0170	0.6458	0.135*
N1	−0.3662 (3)	0.38084 (15)	0.10689 (14)	0.0374 (5)
N2	−0.5209 (3)	0.44225 (16)	0.13189 (15)	0.0419 (5)
N3	−0.3039 (4)	0.22794 (19)	0.37371 (17)	0.0572 (7)
N4	−0.7175 (4)	0.1771 (2)	0.61889 (18)	0.0590 (7)
O1	0.1826 (3)	0.13349 (14)	0.13639 (14)	0.0520 (5)
O2	0.2449 (4)	0.19763 (17)	−0.00730 (16)	0.0689 (6)
O3	−0.3882 (4)	0.16863 (16)	0.44714 (14)	0.0633 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.065 (2)	0.0539 (18)	0.085 (2)	0.0132 (15)	0.0186 (17)	−0.0004 (16)
C2	0.0485 (16)	0.0600 (18)	0.0696 (19)	0.0210 (14)	0.0073 (14)	−0.0002 (15)
C3	0.0457 (14)	0.0414 (13)	0.0458 (15)	0.0024 (11)	0.0136 (12)	−0.0025 (11)
C4	0.0429 (14)	0.0386 (13)	0.0365 (13)	0.0026 (11)	0.0078 (11)	−0.0012 (10)
C5	0.0392 (13)	0.0350 (12)	0.0363 (12)	0.0049 (10)	0.0056 (10)	0.0038 (10)
C6	0.0401 (13)	0.0329 (12)	0.0311 (12)	0.0036 (10)	0.0039 (10)	0.0046 (9)
C7	0.0555 (16)	0.0502 (15)	0.0315 (13)	0.0082 (12)	0.0076 (11)	0.0076 (11)
C8	0.0549 (16)	0.0543 (15)	0.0342 (13)	0.0087 (13)	0.0132 (12)	0.0043 (11)
C9	0.0400 (13)	0.0356 (12)	0.0332 (12)	0.0069 (10)	0.0063 (10)	0.0037 (10)
C10	0.0384 (13)	0.0367 (12)	0.0351 (12)	0.0061 (10)	0.0039 (10)	0.0031 (10)
C11	0.0407 (13)	0.0335 (12)	0.0430 (14)	0.0048 (10)	0.0078 (11)	0.0030 (10)
C12	0.0641 (18)	0.0588 (17)	0.0466 (16)	0.0237 (14)	0.0045 (13)	−0.0007 (13)
C13	0.086 (2)	0.066 (2)	0.0558 (18)	0.0193 (18)	0.0184 (17)	−0.0086 (15)
C14	0.065 (2)	0.0577 (18)	0.087 (2)	0.0223 (16)	0.0309 (18)	−0.0025 (17)
C15	0.0444 (16)	0.0529 (17)	0.087 (2)	0.0141 (13)	0.0048 (15)	0.0008 (16)
C16	0.0408 (14)	0.0412 (14)	0.0570 (16)	0.0055 (11)	0.0037 (12)	0.0020 (12)
C17	0.0440 (13)	0.0370 (12)	0.0314 (12)	0.0096 (10)	0.0066 (10)	0.0034 (10)
C18	0.0437 (14)	0.0512 (15)	0.0383 (13)	0.0078 (12)	0.0073 (11)	0.0102 (11)
C19	0.0552 (16)	0.0468 (14)	0.0409 (14)	0.0075 (12)	0.0145 (12)	0.0065 (11)
C20	0.078 (2)	0.0523 (16)	0.0456 (16)	−0.0024 (15)	0.0160 (14)	0.0106 (13)
C21	0.092 (3)	0.083 (2)	0.0550 (19)	−0.003 (2)	0.0054 (18)	0.0036 (17)
C22	0.064 (2)	0.091 (2)	0.068 (2)	0.0180 (18)	0.0230 (17)	0.0296 (18)
C23	0.065 (2)	0.091 (3)	0.075 (2)	0.0170 (18)	0.0260 (18)	0.0182 (19)
C24	0.116 (3)	0.078 (2)	0.078 (2)	−0.013 (2)	0.034 (2)	0.022 (2)
N1	0.0417 (11)	0.0386 (11)	0.0334 (10)	0.0087 (9)	0.0044 (8)	0.0060 (8)
N2	0.0459 (12)	0.0455 (12)	0.0373 (11)	0.0144 (10)	0.0060 (9)	0.0080 (9)
N3	0.0639 (15)	0.0715 (16)	0.0474 (13)	0.0290 (13)	0.0242 (11)	0.0290 (12)
N4	0.0586 (15)	0.0684 (16)	0.0547 (15)	0.0082 (12)	0.0184 (12)	0.0185 (12)
O1	0.0531 (11)	0.0529 (11)	0.0554 (11)	0.0202 (9)	0.0161 (9)	0.0066 (9)
O2	0.0720 (14)	0.0770 (15)	0.0680 (14)	0.0234 (12)	0.0390 (12)	0.0133 (11)
O3	0.0735 (14)	0.0733 (14)	0.0565 (12)	0.0356 (11)	0.0274 (10)	0.0345 (10)

Geometric parameters (Å, º) top

C1—C2	1.482 (4)	C14—C15	1.373 (5)
C1—H1A	0.9600	C14—H14	0.9300
C1—H1B	0.9600	C15—C16	1.379 (4)
C1—H1C	0.9600	C15—H15	0.9300
C2—O1	1.451 (3)	C16—H16	0.9300
C2—H2A	0.9700	C17—N3	1.311 (3)
C2—H2B	0.9700	C17—C18	1.415 (3)
C3—O2	1.201 (3)	C18—C19	1.340 (4)
C3—O1	1.336 (3)	C18—H18	0.9300
C3—C4	1.493 (4)	C19—O3	1.350 (3)
C4—C5	1.371 (3)	C19—C20	1.494 (4)
C4—C8	1.420 (4)	C20—N4	1.462 (4)
C5—C6	1.407 (3)	C20—H20A	0.9700
C5—H5	0.9300	C20—H20B	0.9700
C6—N1	1.379 (3)	C21—C22	1.528 (5)
C6—C9	1.402 (3)	C21—H21A	0.9600
C7—C8	1.347 (4)	C21—H21B	0.9600
C7—N1	1.370 (3)	C21—H21C	0.9600
C7—H7	0.9300	C22—N4	1.419 (4)
C8—H8	0.9300	C22—H22A	0.9700
C9—C10	1.404 (3)	C22—H22B	0.9700
C9—C17	1.464 (3)	C23—C24	1.476 (5)
C10—N2	1.347 (3)	C23—N4	1.487 (4)
C10—C11	1.480 (3)	C23—H23A	0.9700
C11—C12	1.386 (4)	C23—H23B	0.9700
C11—C16	1.391 (3)	C24—H24A	0.9600
C12—C13	1.384 (4)	C24—H24B	0.9600
C12—H12	0.9300	C24—H24C	0.9600
C13—C14	1.379 (5)	N1—N2	1.358 (3)
C13—H13	0.9300	N3—O3	1.417 (3)

C2—C1—H1A	109.5	C15—C16—H16	119.9
C2—C1—H1B	109.5	C11—C16—H16	119.9
H1A—C1—H1B	109.5	N3—C17—C18	111.6 (2)
C2—C1—H1C	109.5	N3—C17—C9	119.6 (2)
H1A—C1—H1C	109.5	C18—C17—C9	128.7 (2)
H1B—C1—H1C	109.5	C19—C18—C17	105.3 (2)
O1—C2—C1	111.2 (2)	C19—C18—H18	127.4
O1—C2—H2A	109.4	C17—C18—H18	127.4
C1—C2—H2A	109.4	C18—C19—O3	109.4 (2)
O1—C2—H2B	109.4	C18—C19—C20	133.0 (3)
C1—C2—H2B	109.4	O3—C19—C20	117.5 (2)
H2A—C2—H2B	108.0	N4—C20—C19	113.1 (2)
O2—C3—O1	124.2 (2)	N4—C20—H20A	109.0
O2—C3—C4	123.9 (3)	C19—C20—H20A	109.0
O1—C3—C4	111.9 (2)	N4—C20—H20B	109.0
C5—C4—C8	120.0 (2)	C19—C20—H20B	109.0
C5—C4—C3	121.2 (2)	H20A—C20—H20B	107.8
C8—C4—C3	118.8 (2)	C22—C21—H21A	109.5
C4—C5—C6	119.3 (2)	C22—C21—H21B	109.5
C4—C5—H5	120.4	H21A—C21—H21B	109.5
C6—C5—H5	120.4	C22—C21—H21C	109.5
N1—C6—C9	105.8 (2)	H21A—C21—H21C	109.5
N1—C6—C5	118.2 (2)	H21B—C21—H21C	109.5
C9—C6—C5	136.0 (2)	N4—C22—C21	113.7 (3)
C8—C7—N1	118.6 (2)	N4—C22—H22A	108.8
C8—C7—H7	120.7	C21—C22—H22A	108.8
N1—C7—H7	120.7	N4—C22—H22B	108.8
C7—C8—C4	120.7 (2)	C21—C22—H22B	108.8
C7—C8—H8	119.6	H22A—C22—H22B	107.7
C4—C8—H8	119.6	C24—C23—N4	116.8 (3)
C6—C9—C10	104.9 (2)	C24—C23—H23A	108.1
C6—C9—C17	125.0 (2)	N4—C23—H23A	108.1
C10—C9—C17	129.6 (2)	C24—C23—H23B	108.1
N2—C10—C9	112.2 (2)	N4—C23—H23B	108.1
N2—C10—C11	118.0 (2)	H23A—C23—H23B	107.3
C9—C10—C11	129.7 (2)	C23—C24—H24A	109.5
C12—C11—C16	118.7 (2)	C23—C24—H24B	109.5
C12—C11—C10	120.9 (2)	H24A—C24—H24B	109.5
C16—C11—C10	120.3 (2)	C23—C24—H24C	109.5
C13—C12—C11	120.6 (3)	H24A—C24—H24C	109.5
C13—C12—H12	119.7	H24B—C24—H24C	109.5
C11—C12—H12	119.7	N2—N1—C7	124.3 (2)
C14—C13—C12	120.1 (3)	N2—N1—C6	112.60 (19)
C14—C13—H13	119.9	C7—N1—C6	123.1 (2)
C12—C13—H13	119.9	C10—N2—N1	104.49 (18)
C15—C14—C13	119.6 (3)	C17—N3—O3	104.9 (2)
C15—C14—H14	120.2	C22—N4—C20	111.2 (3)
C13—C14—H14	120.2	C22—N4—C23	114.6 (3)
C14—C15—C16	120.7 (3)	C20—N4—C23	110.5 (3)
C14—C15—H15	119.6	C3—O1—C2	117.7 (2)
C16—C15—H15	119.6	C19—O3—N3	108.85 (19)
C15—C16—C11	120.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N2ⁱ	0.93	2.54	3.456 (3)	169
C22—H22A···O3	0.97	2.52	3.218 (3)	129

Symmetry code: (i) −x−1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆N₄O₃
M_r	418.49
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.1250 (7), 13.1425 (16), 13.7139 (16)
α, β, γ (°)	93.600 (2), 95.514 (2), 95.637 (2)
V (Å³)	1090.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.992, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	5453, 3800, 2842
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.187, 1.07
No. of reflections	3800
No. of parameters	281
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.35

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N2ⁱ	0.93	2.54	3.456 (3)	169
C22—H22A···O3	0.97	2.52	3.218 (3)	129

Symmetry code: (i) −x−1, −y+1, −z.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cuny, G. D., Yu, P. B., Laha, J. K., Xing, X. C., Liu, J. F., Lai, C. S., Deng, D. Y., Sachidanandan, C., Bloch, K. D. & Peterson, R. T. (2008). Bioorg. Med. Chem. Lett. 18, 4388–4392. Web of Science CrossRef PubMed CAS Google Scholar
Ge, Y. Q., Jia, J., Li, Y., Yin, L. & Wang, J. W. (2009). Heterocycles, 78, 197–206. CAS Google Scholar
Johns, B. A., Gudmundsson, K. S., Turner, E. M., Allen, S. H., Samano, V. A., Ray, J. A., Freeman, G. A. F., Boyd, L. Jr, Sexton, C. J., Selleseth, D. W., Creechb, K. L. & Monirib, K. R. (2005). Bioorg. Med. Chem. 13, 2397–2411. Web of Science CrossRef PubMed CAS Google Scholar
Lanig, H., Utz, W. & Gmeiner, P. (2001). J. Med. Chem. 44, 1151–1157. Web of Science CrossRef PubMed CAS Google Scholar
Lee, Y. S., Park, S. M., Kim, H. M., Park, S. K., Lee, K., Lee, C. W. & Kim, B. H. (2009). Bioorg. Med. Chem. Lett. 19, 4688–4691. Web of Science CrossRef PubMed CAS Google Scholar
Meng, Q. Y., Yin, L., Liu, W., Jia, J., Zhan, F. X., Ge, Y. Q., Yang, H. & Wang, J. W. (2010). In preparation. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 4| April 2010| Page o723

doi:10.1107/S1600536810004174

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

Ethyl 3-{5-[(di­ethyl­amino)meth­yl]isoxazol-3-yl}-2-phenyl­pyrazolo[1,5-a]pyridine-5-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Ethyl 3-{5-[(diethylamino)methyl]isoxazol-3-yl}-2-phenylpyrazolo[1,5-a]pyridine-5-carboxylate