Ethyl 5-(ethoxy-carbon-yl)-3-(4-methoxy-phen-yl)-1H-pyrazole-1-acetate.

In the title compound, C(17)H(20)N(2)O(5), all bond lengths and angles show normal values. The dihedral angle between the pyrazole ring and the benzene ring is 6.98 (11)°. The mol-ecules are linked by inter-molecular C-H⋯π inter-actions.

Related literature

For related literature, see: Allen et al. (1987 ▶); Brough et al. (2005 ▶); Cheng et al. (2006 ▶); Dong et al. (2007 ▶); Sehon et al. (2006 ▶); Wei et al. (2006 ▶); Xia et al. (2007 ▶).

Experimental

Crystal data

C17H20N2O5

M = 332.35

Triclinic,

a = 7.4267 (1) Å

b = 11.0511 (2) Å

c = 11.7139 (2) Å

α = 106.721 (1)°

β = 97.898 (1)°

γ = 106.796 (1)°

V = 855.59 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 (2) K

0.45 × 0.39 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.846, T max = 0.974

13041 measured reflections

3806 independent reflections

2376 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.166

S = 1.06

3806 reflections

221 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807057297/fj2063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807057297/fj2063Isup2.hkl

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

C17H20N2O5	Z = 2
Mr = 332.35	F000 = 352
Triclinic, P1	Dx = 1.290 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.4267 (1) Å	Cell parameters from 3567 reflections
b = 11.0511 (2) Å	θ = 3.0–24.5º
c = 11.7139 (2) Å	µ = 0.10 mm−1
α = 106.721 (1)º	T = 296 (2) K
β = 97.898 (1)º	Prism, colourless
γ = 106.796 (1)º	0.45 × 0.39 × 0.28 mm
V = 855.59 (3) Å3

Bruker APEXII CCD area-detector diffractometer	3806 independent reflections
Radiation source: fine-focus sealed tube	2376 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 296(2) K	θmax = 27.5º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.846, Tmax = 0.974	k = −14→14
13041 measured reflections	l = −15→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.166	w = 1/[σ2(Fo2) + (0.0775P)2 + 0.1127P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3806 reflections	Δρmax = 0.32 e Å−3
221 parameters	Δρmin = −0.16 e Å−3
3 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (4)

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	−0.7281 (3)	0.0919 (3)	0.9802 (3)	0.1071 (8)
H1A	−0.7815	0.0997	0.9043	0.161*
H1B	−0.8148	0.0990	1.0334	0.161*
H1C	−0.7110	0.0062	0.9639	0.161*
C2	−0.4043 (3)	0.2015 (2)	0.9716 (2)	0.0792 (5)
C3	−0.2328 (3)	0.3033 (2)	1.0311 (2)	0.0871 (6)
H3	−0.2183	0.3626	1.1091	0.104*
C4	−0.0829 (3)	0.3176 (2)	0.9754 (2)	0.0815 (6)
H4	0.0339	0.3872	1.0170	0.098*
C5	−0.0974 (3)	0.23132 (17)	0.85765 (17)	0.0676 (5)
C6	−0.2716 (3)	0.1283 (2)	0.7993 (2)	0.0783 (6)
H6	−0.2865	0.0685	0.7214	0.094*
C7	−0.4285 (3)	0.1127 (2)	0.8567 (2)	0.0823 (6)
H7	−0.5462	0.0432	0.8171	0.099*
C8	0.0682 (3)	0.25088 (16)	0.80054 (16)	0.0645 (5)
C9	0.0946 (3)	0.17110 (17)	0.69185 (17)	0.0674 (5)
H9	0.0062	0.0898	0.6365	0.081*
C10	0.2765 (3)	0.23673 (16)	0.68338 (16)	0.0640 (5)
C11	0.5351 (3)	0.46068 (18)	0.81994 (17)	0.0722 (5)
H11A	0.6397	0.4248	0.8165	0.087*
H11B	0.5551	0.5187	0.9038	0.087*
C12	0.5401 (3)	0.54247 (18)	0.73607 (18)	0.0744 (5)
C13	0.7510 (4)	0.7109 (3)	0.6817 (3)	0.1111 (9)
H13A	0.6755	0.7696	0.6977	0.133*
H13B	0.7114	0.6574	0.5949	0.133*
C14	0.9606 (5)	0.7918 (3)	0.7167 (3)	0.1405 (13)
H14A	0.9996	0.8409	0.8034	0.211*
H14B	0.9843	0.8539	0.6730	0.211*
H14C	1.0335	0.7330	0.6963	0.211*
C15	0.3773 (3)	0.19420 (18)	0.58813 (18)	0.0714 (5)
C16	0.6729 (3)	0.2462 (3)	0.5236 (2)	0.0952 (7)
H16A	0.6079	0.2275	0.4395	0.114*
H16B	0.7006	0.1670	0.5287	0.114*
C17	0.8560 (4)	0.3647 (3)	0.5629 (3)	0.1128 (9)
H17A	0.8293	0.4383	0.5452	0.169*
H17B	0.9483	0.3412	0.5193	0.169*
H17C	0.9080	0.3909	0.6496	0.169*
N1	0.2268 (2)	0.36044 (14)	0.85650 (14)	0.0697 (4)
N2	0.3521 (2)	0.35071 (14)	0.78541 (14)	0.0664 (4)
O1	−0.5490 (2)	0.19486 (17)	1.03670 (16)	0.1040 (5)
O2	0.4038 (2)	0.53626 (15)	0.66541 (16)	0.1015 (5)
O3	0.7201 (2)	0.62366 (14)	0.75458 (13)	0.0866 (5)
O4	0.3061 (2)	0.08992 (16)	0.50282 (15)	0.1068 (6)
O5	0.55182 (19)	0.28057 (13)	0.60626 (13)	0.0793 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0884 (16)	0.0961 (16)	0.127 (2)	0.0173 (13)	0.0019 (14)	0.0497 (15)
C2	0.0858 (13)	0.0741 (12)	0.0800 (12)	0.0337 (11)	0.0114 (10)	0.0275 (9)
C3	0.0879 (15)	0.0757 (13)	0.0808 (14)	0.0253 (11)	0.0101 (12)	0.0105 (10)
C4	0.0789 (13)	0.0690 (12)	0.0812 (14)	0.0205 (10)	0.0088 (11)	0.0137 (10)
C5	0.0714 (11)	0.0561 (9)	0.0686 (11)	0.0195 (8)	0.0012 (9)	0.0217 (8)
C6	0.0816 (13)	0.0689 (11)	0.0720 (12)	0.0169 (10)	0.0042 (10)	0.0220 (9)
C7	0.0760 (12)	0.0665 (11)	0.0860 (13)	0.0112 (9)	−0.0028 (10)	0.0234 (9)
C8	0.0682 (11)	0.0522 (9)	0.0622 (10)	0.0151 (8)	−0.0010 (8)	0.0176 (8)
C9	0.0697 (11)	0.0500 (9)	0.0656 (11)	0.0123 (8)	−0.0031 (9)	0.0129 (8)
C10	0.0688 (11)	0.0497 (8)	0.0575 (10)	0.0127 (8)	−0.0034 (8)	0.0119 (7)
C11	0.0730 (11)	0.0625 (10)	0.0548 (10)	0.0035 (8)	−0.0051 (8)	0.0118 (8)
C12	0.0791 (12)	0.0573 (10)	0.0655 (11)	0.0093 (9)	−0.0017 (10)	0.0136 (8)
C13	0.129 (2)	0.0820 (15)	0.1059 (19)	0.0067 (14)	0.0078 (16)	0.0480 (14)
C14	0.146 (3)	0.106 (2)	0.127 (2)	−0.0186 (19)	0.021 (2)	0.0466 (18)
C15	0.0744 (12)	0.0624 (10)	0.0650 (11)	0.0193 (9)	0.0023 (9)	0.0152 (9)
C16	0.0941 (16)	0.1076 (17)	0.0903 (16)	0.0433 (14)	0.0266 (13)	0.0332 (13)
C17	0.0953 (17)	0.1129 (19)	0.150 (3)	0.0370 (15)	0.0466 (17)	0.0653 (19)
N1	0.0757 (10)	0.0590 (8)	0.0591 (9)	0.0129 (7)	0.0038 (8)	0.0144 (7)
N2	0.0691 (9)	0.0556 (8)	0.0563 (8)	0.0093 (7)	−0.0014 (7)	0.0127 (6)
O1	0.0940 (11)	0.0954 (11)	0.1023 (12)	0.0215 (9)	0.0206 (9)	0.0175 (9)
O2	0.0943 (10)	0.0906 (10)	0.1036 (12)	0.0156 (8)	−0.0142 (9)	0.0441 (9)
O3	0.0868 (9)	0.0727 (8)	0.0778 (9)	0.0016 (7)	0.0001 (7)	0.0287 (7)
O4	0.0975 (11)	0.0835 (10)	0.0917 (11)	0.0104 (8)	0.0154 (9)	−0.0146 (8)
O5	0.0756 (8)	0.0742 (8)	0.0753 (9)	0.0172 (7)	0.0137 (7)	0.0178 (7)

C1—O1	1.397 (3)	C11—C12	1.512 (3)
C1—H1A	0.9600	C11—H11A	0.9700
C1—H1B	0.9600	C11—H11B	0.9700
C1—H1C	0.9600	C12—O2	1.188 (2)
C2—C3	1.360 (3)	C12—O3	1.325 (2)
C2—C7	1.370 (3)	C13—O3	1.452 (3)
C2—O1	1.398 (3)	C13—C14	1.483 (4)
C3—C4	1.359 (3)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.402 (3)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.377 (2)	C14—H14C	0.9600
C5—C8	1.470 (3)	C15—O4	1.203 (2)
C6—C7	1.417 (3)	C15—O5	1.315 (2)
C6—H6	0.9300	C16—O5	1.455 (3)
C7—H7	0.9300	C16—C17	1.492 (3)
C8—N1	1.338 (2)	C16—H16A	0.9700
C8—C9	1.400 (3)	C16—H16B	0.9700
C9—C10	1.369 (3)	C17—H17A	0.9600
C9—H9	0.9300	C17—H17B	0.9600
C10—N2	1.368 (2)	C17—H17C	0.9600
C10—C15	1.469 (3)	N1—N2	1.338 (2)
C11—N2	1.449 (2)
O1—C1—H1A	109.5	H11A—C11—H11B	108.0
O1—C1—H1B	109.5	O2—C12—O3	125.12 (19)
H1A—C1—H1B	109.5	O2—C12—C11	125.49 (19)
O1—C1—H1C	109.5	O3—C12—C11	109.39 (16)
H1A—C1—H1C	109.5	O3—C13—C14	107.6 (2)
H1B—C1—H1C	109.5	O3—C13—H13A	110.2
C3—C2—C7	121.2 (2)	C14—C13—H13A	110.2
C3—C2—O1	115.1 (2)	O3—C13—H13B	110.2
C7—C2—O1	123.7 (2)	C14—C13—H13B	110.2
C4—C3—C2	119.4 (2)	H13A—C13—H13B	108.5
C4—C3—H3	120.3	C13—C14—H14A	109.5
C2—C3—H3	120.3	C13—C14—H14B	109.5
C3—C4—C5	122.6 (2)	H14A—C14—H14B	109.5
C3—C4—H4	118.7	C13—C14—H14C	109.5
C5—C4—H4	118.7	H14A—C14—H14C	109.5
C6—C5—C4	117.2 (2)	H14B—C14—H14C	109.5
C6—C5—C8	122.06 (18)	O4—C15—O5	123.9 (2)
C4—C5—C8	120.78 (17)	O4—C15—C10	122.73 (19)
C5—C6—C7	120.6 (2)	O5—C15—C10	113.38 (15)
C5—C6—H6	119.7	O5—C16—C17	106.8 (2)
C7—C6—H6	119.7	O5—C16—H16A	110.4
C2—C7—C6	119.0 (2)	C17—C16—H16A	110.4
C2—C7—H7	120.5	O5—C16—H16B	110.4
C6—C7—H7	120.5	C17—C16—H16B	110.4
N1—C8—C9	110.03 (17)	H16A—C16—H16B	108.6
N1—C8—C5	119.14 (17)	C16—C17—H17A	109.5
C9—C8—C5	130.83 (16)	C16—C17—H17B	109.5
C10—C9—C8	106.19 (15)	H17A—C17—H17B	109.5
C10—C9—H9	126.9	C16—C17—H17C	109.5
C8—C9—H9	126.9	H17A—C17—H17C	109.5
N2—C10—C9	106.01 (17)	H17B—C17—H17C	109.5
N2—C10—C15	125.70 (17)	C8—N1—N2	105.97 (15)
C9—C10—C15	128.25 (16)	N1—N2—C10	111.79 (15)
N2—C11—C12	111.51 (14)	N1—N2—C11	118.33 (14)
N2—C11—H11A	109.3	C10—N2—C11	129.73 (18)
C12—C11—H11A	109.3	C1—O1—C2	117.6 (2)
N2—C11—H11B	109.3	C12—O3—C13	116.71 (17)
C12—C11—H11B	109.3	C15—O5—C16	118.99 (16)
C7—C2—C3—C4	0.2 (3)	C9—C10—C15—O4	−0.7 (3)
O1—C2—C3—C4	179.65 (19)	N2—C10—C15—O5	−2.6 (3)
C2—C3—C4—C5	0.3 (3)	C9—C10—C15—O5	179.77 (16)
C3—C4—C5—C6	−0.7 (3)	C9—C8—N1—N2	−0.21 (18)
C3—C4—C5—C8	179.64 (18)	C5—C8—N1—N2	179.32 (14)
C4—C5—C6—C7	0.6 (3)	C8—N1—N2—C10	0.48 (19)
C8—C5—C6—C7	−179.75 (16)	C8—N1—N2—C11	176.47 (14)
C3—C2—C7—C6	−0.3 (3)	C9—C10—N2—N1	−0.56 (19)
O1—C2—C7—C6	−179.68 (18)	C15—C10—N2—N1	−178.58 (15)
C5—C6—C7—C2	−0.1 (3)	C9—C10—N2—C11	−175.96 (16)
C6—C5—C8—N1	173.34 (16)	C15—C10—N2—C11	6.0 (3)
C4—C5—C8—N1	−7.0 (2)	C12—C11—N2—N1	−106.75 (19)
C6—C5—C8—C9	−7.2 (3)	C12—C11—N2—C10	68.4 (2)
C4—C5—C8—C9	172.38 (18)	C3—C2—O1—C1	−179.77 (19)
N1—C8—C9—C10	−0.12 (19)	C7—C2—O1—C1	−0.4 (3)
C5—C8—C9—C10	−179.58 (16)	O2—C12—O3—C13	−0.3 (3)
C8—C9—C10—N2	0.40 (18)	C11—C12—O3—C13	−179.51 (19)
C8—C9—C10—C15	178.35 (16)	C14—C13—O3—C12	−179.8 (2)
N2—C11—C12—O2	13.2 (3)	O4—C15—O5—C16	−4.0 (3)
N2—C11—C12—O3	−167.54 (16)	C10—C15—O5—C16	175.57 (16)
N2—C10—C15—O4	176.88 (19)	C17—C16—O5—C15	177.34 (17)

X—H···Cg	X—H	H···Cg	X···Cg	X—H···Cg
C1—H1A···Cg1i	0.96	2.89	3.731 (3)	147

Table 1

X—H⋯π-ring interactions calculated by PLATON (Spek, 2003 ▶). Cg i is a centroid of the pyrazole ring N1/N2/C8/C9/C10

X—H⋯Cg	X—H	H⋯Cg	X⋯Cg	X—H⋯Cg
C1—H1A⋯Cg1i	0.96	2.89	3.731 (3)	147

Symmetry code: (i) . Cg1 is the centroid of the the pyrazole ring.