Ethyl 3-{5-[(diethyl-amino)meth-yl]isoxazol-3-yl}-2-phenyl-pyrazolo[1,5-a]pyridine-5-carboxyl-ate.

In the title compound, C(24)H(26)N(4)O(3), 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 mol-ecules are linked by a pair of C-H⋯N hydrogen bonds, forming a centrosymmetric dimer. A weak intra-molecular C-H⋯O inter-action 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 = 418.49

Triclinic,

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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.187

S = 1.07

3800 reflections

281 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.35 e Å−3

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.

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

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

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

C24H26N4O3	Z = 2
Mr = 418.49	F(000) = 444
Triclinic, P1	Dx = 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

Bruker APEXII CCD area-detector diffractometer	3800 independent reflections
Radiation source: fine-focus sealed tube	2842 reflections with I > 2σ(I)
graphite	Rint = 0.014
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 1.5°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→13
Tmin = 0.992, Tmax = 0.992	l = −14→16
5453 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0993P)2 + 0.4336P] where P = (Fo2 + 2Fc2)/3
3800 reflections	(Δ/σ)max = 0.004
281 parameters	Δρmax = 0.75 e Å−3
1 restraint	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .