Ethyl 6-methyl-2-p-tolyl-pyrazolo[1,5-a]pyridine-5-carboxyl-ate.

In the title mol-ecule, C(18)H(18)N(2)O(2), the bicyclic ring system and the benzene ring form a dihedral angle of 13.45 (3)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into chains propagated along [201].

Related literature

For novel pyrazolo[1,5-a]pyridine compounds, see: Ge et al. (2009 ▶). For a related structure, see: Shao et al. (2009 ▶).

Experimental

Crystal data

C18H18N2O2

M = 294.34

Monoclinic,

a = 6.8352 (3) Å

b = 30.3999 (11) Å

c = 7.5409 (3) Å

β = 97.375 (2)°

V = 1553.96 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.43 × 0.32 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.965, T max = 0.983

18651 measured reflections

3181 independent reflections

2166 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.148

S = 1.07

3181 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035314/cv2611sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035314/cv2611Isup2.hkl

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

C18H18N2O2	F(000) = 624
Mr = 294.34	Dx = 1.258 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4574 reflections
a = 6.8352 (3) Å	θ = 2.7–24.2°
b = 30.3999 (11) Å	µ = 0.08 mm−1
c = 7.5409 (3) Å	T = 293 K
β = 97.375 (2)°	Block, colourless
V = 1553.96 (11) Å3	0.43 × 0.32 × 0.21 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3181 independent reflections
Radiation source: fine-focus sealed tube	2166 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 26.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.965, Tmax = 0.983	k = −37→37
18651 measured reflections	l = −9→9

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.5452P] where P = (Fo2 + 2Fc2)/3
3181 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.22 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
N1	0.3372 (2)	0.65607 (5)	0.5370 (2)	0.0429 (4)
N2	0.3988 (2)	0.61395 (6)	0.5589 (2)	0.0482 (4)
O2	0.3651 (2)	0.81645 (4)	0.5569 (2)	0.0561 (4)
O3	0.0666 (3)	0.80858 (6)	0.4073 (3)	0.0806 (6)
C1	1.0771 (5)	0.46224 (8)	0.7690 (4)	0.0820 (8)
H1A	1.2123	0.4711	0.7975	0.123*
H1B	1.0627	0.4450	0.6615	0.123*
H1C	1.0386	0.4450	0.8654	0.123*
C2	0.9475 (4)	0.50258 (8)	0.7418 (3)	0.0589 (6)
C3	1.0264 (4)	0.54415 (8)	0.7553 (3)	0.0638 (6)
H3A	1.1619	0.5474	0.7852	0.077*
C4	0.9101 (3)	0.58130 (7)	0.7255 (3)	0.0563 (6)
H4A	0.9683	0.6090	0.7366	0.068*
C5	0.7080 (3)	0.57786 (6)	0.6794 (3)	0.0460 (5)
C6	0.6282 (4)	0.53587 (7)	0.6683 (3)	0.0636 (6)
H6A	0.4927	0.5324	0.6392	0.076*
C7	0.7463 (4)	0.49920 (8)	0.6995 (4)	0.0695 (7)
H7A	0.6885	0.4715	0.6918	0.083*
C8	0.5871 (3)	0.61754 (6)	0.6386 (3)	0.0435 (5)
C9	0.6428 (3)	0.66109 (7)	0.6684 (3)	0.0464 (5)
H9A	0.7643	0.6714	0.7221	0.056*
C10	0.4813 (3)	0.68603 (6)	0.6023 (3)	0.0423 (5)
C11	0.4335 (3)	0.73089 (6)	0.5842 (3)	0.0440 (5)
H11A	0.5260	0.7519	0.6288	0.053*
C12	0.2535 (3)	0.74423 (7)	0.5024 (2)	0.0412 (5)
C13	0.1075 (3)	0.71204 (7)	0.4353 (3)	0.0441 (5)
C14	0.1553 (3)	0.66890 (7)	0.4564 (3)	0.0473 (5)
H14A	0.0628	0.6476	0.4153	0.057*
C15	−0.0942 (3)	0.72349 (8)	0.3412 (3)	0.0557 (6)
H15A	−0.1660	0.6970	0.3083	0.084*
H15B	−0.0807	0.7403	0.2357	0.084*
H15C	−0.1644	0.7405	0.4197	0.084*
C16	0.2140 (3)	0.79236 (7)	0.4827 (3)	0.0476 (5)
C17	0.3473 (4)	0.86376 (7)	0.5387 (3)	0.0624 (6)
H17A	0.2408	0.8744	0.6007	0.075*
H17B	0.3190	0.8718	0.4135	0.075*
C18	0.5387 (4)	0.88348 (8)	0.6182 (3)	0.0757 (8)
H18A	0.5313	0.9149	0.6078	0.114*
H18B	0.6429	0.8727	0.5557	0.114*
H18C	0.5649	0.8755	0.7421	0.114*

	U11	U22	U33	U12	U13	U23
N1	0.0375 (9)	0.0432 (10)	0.0472 (9)	−0.0043 (7)	0.0016 (7)	−0.0009 (7)
N2	0.0473 (10)	0.0404 (10)	0.0560 (10)	−0.0027 (8)	0.0035 (8)	−0.0002 (8)
O2	0.0546 (9)	0.0407 (9)	0.0710 (10)	−0.0009 (7)	0.0008 (7)	0.0056 (7)
O3	0.0562 (10)	0.0558 (11)	0.1210 (15)	0.0076 (8)	−0.0225 (10)	0.0140 (10)
C1	0.101 (2)	0.0602 (17)	0.0863 (19)	0.0314 (15)	0.0167 (16)	0.0084 (14)
C2	0.0711 (17)	0.0490 (14)	0.0574 (13)	0.0134 (12)	0.0116 (11)	0.0033 (10)
C3	0.0520 (14)	0.0598 (16)	0.0790 (17)	0.0093 (12)	0.0058 (12)	0.0061 (12)
C4	0.0516 (13)	0.0448 (13)	0.0719 (15)	0.0004 (10)	0.0062 (11)	0.0037 (11)
C5	0.0476 (12)	0.0423 (12)	0.0487 (11)	0.0007 (9)	0.0078 (9)	−0.0003 (9)
C6	0.0553 (14)	0.0488 (14)	0.0850 (17)	−0.0039 (11)	0.0027 (12)	−0.0019 (12)
C7	0.0785 (18)	0.0384 (13)	0.0909 (19)	−0.0012 (12)	0.0081 (14)	0.0013 (12)
C8	0.0414 (11)	0.0436 (12)	0.0454 (11)	−0.0024 (9)	0.0050 (9)	0.0006 (9)
C9	0.0388 (11)	0.0441 (12)	0.0547 (12)	−0.0031 (9)	−0.0007 (9)	0.0001 (9)
C10	0.0372 (10)	0.0432 (12)	0.0455 (11)	−0.0049 (9)	0.0022 (8)	−0.0004 (8)
C11	0.0405 (11)	0.0407 (11)	0.0500 (11)	−0.0051 (9)	0.0022 (9)	−0.0001 (9)
C12	0.0374 (10)	0.0451 (12)	0.0411 (10)	−0.0001 (9)	0.0045 (8)	0.0038 (8)
C13	0.0361 (10)	0.0534 (13)	0.0425 (11)	−0.0011 (9)	0.0036 (8)	0.0030 (9)
C14	0.0367 (11)	0.0533 (13)	0.0502 (12)	−0.0071 (9)	−0.0008 (9)	−0.0013 (9)
C15	0.0408 (12)	0.0626 (14)	0.0609 (14)	−0.0007 (10)	−0.0042 (10)	0.0036 (11)
C16	0.0406 (11)	0.0510 (13)	0.0512 (12)	0.0006 (10)	0.0055 (9)	0.0055 (10)
C17	0.0741 (17)	0.0418 (13)	0.0731 (16)	0.0030 (12)	0.0157 (13)	0.0056 (11)
C18	0.094 (2)	0.0588 (16)	0.0740 (17)	−0.0194 (14)	0.0101 (15)	−0.0054 (13)

N1—N2	1.351 (2)	C7—H7A	0.9300
N1—C14	1.369 (2)	C8—C9	1.388 (3)
N1—C10	1.385 (2)	C9—C10	1.379 (3)
N2—C8	1.353 (2)	C9—H9A	0.9300
O2—C16	1.330 (2)	C10—C11	1.405 (3)
O2—C17	1.448 (3)	C11—C12	1.365 (3)
O3—C16	1.198 (2)	C11—H11A	0.9300
C1—C2	1.511 (3)	C12—C13	1.442 (3)
C1—H1A	0.9600	C12—C16	1.492 (3)
C1—H1B	0.9600	C13—C14	1.356 (3)
C1—H1C	0.9600	C13—C15	1.508 (3)
C2—C3	1.373 (3)	C14—H14A	0.9300
C2—C7	1.375 (4)	C15—H15A	0.9600
C3—C4	1.383 (3)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—C5	1.384 (3)	C17—C18	1.493 (3)
C4—H4A	0.9300	C17—H17A	0.9700
C5—C6	1.386 (3)	C17—H17B	0.9700
C5—C8	1.472 (3)	C18—H18A	0.9600
C6—C7	1.379 (3)	C18—H18B	0.9600
C6—H6A	0.9300	C18—H18C	0.9600
N2—N1—C14	125.13 (17)	C9—C10—C11	137.25 (19)
N2—N1—C10	112.56 (16)	N1—C10—C11	117.27 (17)
C14—N1—C10	122.30 (17)	C12—C11—C10	121.13 (18)
N1—N2—C8	103.98 (15)	C12—C11—H11A	119.4
C16—O2—C17	117.10 (17)	C10—C11—H11A	119.4
C2—C1—H1A	109.5	C11—C12—C13	120.00 (19)
C2—C1—H1B	109.5	C11—C12—C16	118.51 (18)
H1A—C1—H1B	109.5	C13—C12—C16	121.49 (17)
C2—C1—H1C	109.5	C14—C13—C12	117.99 (18)
H1A—C1—H1C	109.5	C14—C13—C15	118.08 (18)
H1B—C1—H1C	109.5	C12—C13—C15	123.93 (19)
C3—C2—C7	117.3 (2)	C13—C14—N1	121.30 (19)
C3—C2—C1	121.3 (2)	C13—C14—H14A	119.3
C7—C2—C1	121.5 (2)	N1—C14—H14A	119.3
C2—C3—C4	121.8 (2)	C13—C15—H15A	109.5
C2—C3—H3A	119.1	C13—C15—H15B	109.5
C4—C3—H3A	119.1	H15A—C15—H15B	109.5
C3—C4—C5	120.9 (2)	C13—C15—H15C	109.5
C3—C4—H4A	119.6	H15A—C15—H15C	109.5
C5—C4—H4A	119.6	H15B—C15—H15C	109.5
C4—C5—C6	117.2 (2)	O3—C16—O2	122.3 (2)
C4—C5—C8	120.38 (19)	O3—C16—C12	125.6 (2)
C6—C5—C8	122.4 (2)	O2—C16—C12	112.17 (17)
C7—C6—C5	121.1 (2)	O2—C17—C18	107.6 (2)
C7—C6—H6A	119.4	O2—C17—H17A	110.2
C5—C6—H6A	119.4	C18—C17—H17A	110.2
C2—C7—C6	121.7 (2)	O2—C17—H17B	110.2
C2—C7—H7A	119.2	C18—C17—H17B	110.2
C6—C7—H7A	119.2	H17A—C17—H17B	108.5
N2—C8—C9	111.98 (17)	C17—C18—H18A	109.5
N2—C8—C5	120.22 (18)	C17—C18—H18B	109.5
C9—C8—C5	127.78 (18)	H18A—C18—H18B	109.5
C10—C9—C8	106.01 (17)	C17—C18—H18C	109.5
C10—C9—H9A	127.0	H18A—C18—H18C	109.5
C8—C9—H9A	127.0	H18B—C18—H18C	109.5
C9—C10—N1	105.47 (17)
C14—N1—N2—C8	178.09 (17)	C14—N1—C10—C9	−178.47 (17)
C10—N1—N2—C8	−0.5 (2)	N2—N1—C10—C11	179.20 (16)
C7—C2—C3—C4	−0.8 (4)	C14—N1—C10—C11	0.5 (3)
C1—C2—C3—C4	178.1 (2)	C9—C10—C11—C12	177.3 (2)
C2—C3—C4—C5	−0.5 (4)	N1—C10—C11—C12	−1.3 (3)
C3—C4—C5—C6	1.3 (3)	C10—C11—C12—C13	1.0 (3)
C3—C4—C5—C8	−176.7 (2)	C10—C11—C12—C16	−178.23 (18)
C4—C5—C6—C7	−0.9 (4)	C11—C12—C13—C14	0.0 (3)
C8—C5—C6—C7	177.0 (2)	C16—C12—C13—C14	179.22 (18)
C3—C2—C7—C6	1.2 (4)	C11—C12—C13—C15	−179.27 (19)
C1—C2—C7—C6	−177.6 (2)	C16—C12—C13—C15	−0.1 (3)
C5—C6—C7—C2	−0.4 (4)	C12—C13—C14—N1	−0.7 (3)
N1—N2—C8—C9	0.7 (2)	C15—C13—C14—N1	178.58 (18)
N1—N2—C8—C5	−178.00 (17)	N2—N1—C14—C13	−178.02 (18)
C4—C5—C8—N2	166.40 (19)	C10—N1—C14—C13	0.5 (3)
C6—C5—C8—N2	−11.4 (3)	C17—O2—C16—O3	−1.8 (3)
C4—C5—C8—C9	−12.0 (3)	C17—O2—C16—C12	177.15 (17)
C6—C5—C8—C9	170.1 (2)	C11—C12—C16—O3	176.6 (2)
N2—C8—C9—C10	−0.6 (2)	C13—C12—C16—O3	−2.6 (3)
C5—C8—C9—C10	177.97 (19)	C11—C12—C16—O2	−2.3 (3)
C8—C9—C10—N1	0.2 (2)	C13—C12—C16—O2	178.51 (17)
C8—C9—C10—C11	−178.5 (2)	C16—O2—C17—C18	−175.41 (18)
N2—N1—C10—C9	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O3i	0.93	2.42	3.339 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O3i	0.93	2.42	3.339 (3)	170

Symmetry code: (i) .