Ethyl 1-benzyl-3-(4-methyl-phen-yl)-1H-pyrazole-5-carboxyl-ate.

In the title compound, C(20)H(20)N(2)O(2), the pyrazole ring makes dihedral angles of 15.68 (4) and 83.40 (4)°, respectively, with the tolyl and benzyl rings, respectively.

Related literature

For arelated structure, see: Ge et al. (2007 ▶). For applications of nitro­gen-containing heterocyclic compounds in agrochemicals and pharmaceuticals, see: Ge et al. (2009a ▶,b ▶, 2011 ▶).

Experimental

Crystal data

C20H20N2O2

M = 320.38

Triclinic,

a = 7.666 (4) Å

b = 10.160 (6) Å

c = 11.381 (7) Å

α = 83.991 (9)°

β = 87.466 (9)°

γ = 85.47 (1)°

V = 878.2 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.21 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.984, T max = 0.991

4489 measured reflections

3045 independent reflections

2182 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.220

S = 1.06

3045 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536811002339/jh2257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002339/jh2257Isup2.hkl

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

C20H20N2O2	Z = 2
Mr = 320.38	F(000) = 340
Triclinic, P1	Dx = 1.212 Mg m−3
a = 7.666 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.160 (6) Å	Cell parameters from 1778 reflections
c = 11.381 (7) Å	θ = 2.6–24.2°
α = 83.991 (9)°	µ = 0.08 mm−1
β = 87.466 (9)°	T = 298 K
γ = 85.47 (1)°	BLOCK, white
V = 878.2 (9) Å3	0.21 × 0.16 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	3045 independent reflections
Radiation source: fine-focus sealed tube	2182 reflections with I > 2σ(I)
graphite	Rint = 0.032
phi and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→8
Tmin = 0.984, Tmax = 0.991	k = −12→9
4489 measured reflections	l = −13→13

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.220	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1348P)2 + 0.1525P] where P = (Fo2 + 2Fc2)/3
3045 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.21 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
O1	0.3059 (3)	0.5585 (2)	0.70282 (17)	0.0826 (7)
O2	0.2483 (3)	0.6693 (2)	0.86211 (17)	0.0703 (6)
N1	0.3539 (3)	0.3185 (2)	0.86746 (18)	0.0548 (6)
N2	0.3537 (3)	0.2290 (2)	0.96361 (19)	0.0569 (6)
C1	0.1960 (6)	0.9004 (4)	0.8654 (3)	0.0955 (11)
H1A	0.1004	0.8824	0.9206	0.143*
H1B	0.1698	0.9836	0.8191	0.143*
H1C	0.3006	0.9049	0.9077	0.143*
C2	0.2227 (5)	0.7932 (3)	0.7865 (3)	0.0764 (9)
H2A	0.1213	0.7919	0.7387	0.092*
H2B	0.3246	0.8065	0.7342	0.092*
C3	0.2870 (3)	0.5601 (3)	0.8081 (2)	0.0597 (7)
C4	0.3021 (3)	0.4439 (3)	0.8954 (2)	0.0528 (6)
C5	0.2658 (3)	0.4323 (3)	1.0152 (2)	0.0551 (7)
H5	0.2268	0.5002	1.0609	0.066*
C6	0.2990 (3)	0.2986 (3)	1.0543 (2)	0.0517 (6)
C7	0.2828 (3)	0.2321 (3)	1.1751 (2)	0.0523 (6)
C8	0.2692 (4)	0.3059 (3)	1.2712 (2)	0.0625 (7)
H8	0.2707	0.3978	1.2586	0.075*
C9	0.2535 (4)	0.2459 (3)	1.3851 (2)	0.0669 (8)
H9	0.2442	0.2982	1.4478	0.080*
C10	0.2512 (4)	0.1096 (3)	1.4083 (2)	0.0616 (7)
C11	0.2643 (4)	0.0367 (3)	1.3121 (3)	0.0717 (8)
H11	0.2620	−0.0551	1.3247	0.086*
C12	0.2806 (4)	0.0958 (3)	1.1980 (2)	0.0648 (8)
H12	0.2903	0.0433	1.1355	0.078*
C13	0.2361 (5)	0.0423 (4)	1.5327 (3)	0.0880 (10)
H13A	0.2140	−0.0490	1.5301	0.132*
H13B	0.1414	0.0861	1.5752	0.132*
H13C	0.3434	0.0471	1.5719	0.132*
C14	0.4189 (3)	0.2742 (3)	0.7545 (2)	0.0608 (7)
H14A	0.3443	0.3163	0.6925	0.073*
H14B	0.4110	0.1791	0.7574	0.073*
C15	0.6048 (3)	0.3050 (2)	0.7234 (2)	0.0485 (6)
C16	0.6535 (4)	0.3469 (3)	0.6073 (2)	0.0596 (7)
H16	0.5692	0.3606	0.5501	0.071*
C17	0.8246 (4)	0.3682 (3)	0.5762 (3)	0.0730 (9)
H17	0.8563	0.3945	0.4979	0.088*
C18	0.9483 (4)	0.3509 (4)	0.6601 (3)	0.0766 (9)
H18	1.0637	0.3675	0.6390	0.092*
C19	0.9039 (4)	0.3090 (3)	0.7758 (3)	0.0692 (8)
H19	0.9892	0.2966	0.8324	0.083*
C20	0.7326 (3)	0.2855 (3)	0.8074 (2)	0.0555 (7)
H20	0.7025	0.2566	0.8853	0.067*

	U11	U22	U33	U12	U13	U23
O1	0.1089 (17)	0.0879 (17)	0.0500 (12)	−0.0083 (13)	−0.0052 (10)	−0.0005 (11)
O2	0.0972 (15)	0.0575 (12)	0.0542 (11)	−0.0067 (10)	−0.0058 (9)	0.0058 (9)
N1	0.0577 (12)	0.0589 (14)	0.0494 (12)	−0.0112 (10)	0.0018 (9)	−0.0093 (10)
N2	0.0608 (13)	0.0548 (13)	0.0561 (13)	−0.0100 (10)	0.0022 (10)	−0.0083 (10)
C1	0.131 (3)	0.061 (2)	0.091 (2)	−0.0049 (19)	−0.015 (2)	0.0112 (18)
C2	0.091 (2)	0.065 (2)	0.0695 (19)	−0.0083 (16)	−0.0136 (16)	0.0169 (16)
C3	0.0604 (16)	0.0674 (18)	0.0520 (16)	−0.0112 (13)	−0.0059 (11)	−0.0031 (13)
C4	0.0542 (14)	0.0551 (16)	0.0501 (14)	−0.0110 (11)	−0.0027 (11)	−0.0037 (12)
C5	0.0643 (16)	0.0517 (15)	0.0500 (14)	−0.0065 (12)	0.0008 (11)	−0.0082 (11)
C6	0.0545 (14)	0.0512 (15)	0.0509 (14)	−0.0089 (11)	0.0025 (11)	−0.0098 (11)
C7	0.0545 (14)	0.0491 (15)	0.0531 (14)	−0.0051 (11)	0.0026 (11)	−0.0056 (11)
C8	0.0851 (19)	0.0470 (15)	0.0561 (16)	−0.0106 (13)	0.0011 (13)	−0.0061 (12)
C9	0.089 (2)	0.0595 (18)	0.0530 (16)	−0.0082 (15)	0.0023 (14)	−0.0104 (13)
C10	0.0716 (17)	0.0582 (17)	0.0534 (15)	−0.0028 (13)	0.0007 (12)	−0.0007 (12)
C11	0.103 (2)	0.0443 (16)	0.0660 (18)	−0.0029 (14)	0.0045 (16)	−0.0023 (13)
C12	0.091 (2)	0.0462 (15)	0.0567 (16)	−0.0007 (13)	0.0029 (14)	−0.0081 (12)
C13	0.123 (3)	0.079 (2)	0.0594 (19)	−0.008 (2)	−0.0044 (18)	0.0073 (16)
C14	0.0632 (16)	0.0726 (19)	0.0512 (14)	−0.0156 (13)	−0.0016 (12)	−0.0198 (13)
C15	0.0543 (14)	0.0459 (14)	0.0472 (13)	−0.0054 (10)	−0.0033 (10)	−0.0120 (10)
C16	0.0669 (17)	0.0637 (17)	0.0481 (14)	−0.0030 (13)	−0.0076 (12)	−0.0048 (12)
C17	0.0712 (19)	0.087 (2)	0.0594 (17)	−0.0095 (16)	0.0107 (14)	−0.0026 (15)
C18	0.0563 (17)	0.092 (2)	0.081 (2)	−0.0046 (15)	0.0081 (15)	−0.0122 (18)
C19	0.0549 (16)	0.084 (2)	0.0699 (18)	0.0027 (14)	−0.0142 (13)	−0.0154 (16)
C20	0.0669 (16)	0.0551 (15)	0.0456 (13)	−0.0038 (12)	−0.0063 (11)	−0.0096 (11)

O1—C3	1.202 (3)	C9—H9	0.9300
O2—C3	1.332 (3)	C10—C11	1.381 (4)
O2—C2	1.453 (3)	C10—C13	1.510 (4)
N1—N2	1.348 (3)	C11—C12	1.376 (4)
N1—C4	1.369 (3)	C11—H11	0.9300
N1—C14	1.461 (3)	C12—H12	0.9300
N2—C6	1.345 (3)	C13—H13A	0.9600
C1—C2	1.480 (5)	C13—H13B	0.9600
C1—H1A	0.9600	C13—H13C	0.9600
C1—H1B	0.9600	C14—C15	1.502 (3)
C1—H1C	0.9600	C14—H14A	0.9700
C2—H2A	0.9700	C14—H14B	0.9700
C2—H2B	0.9700	C15—C20	1.388 (4)
C3—C4	1.463 (4)	C15—C16	1.389 (4)
C4—C5	1.374 (3)	C16—C17	1.372 (4)
C5—C6	1.392 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.364 (4)
C6—C7	1.471 (4)	C17—H17	0.9300
C7—C12	1.384 (4)	C18—C19	1.377 (4)
C7—C8	1.386 (4)	C18—H18	0.9300
C8—C9	1.378 (4)	C19—C20	1.379 (4)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.384 (4)	C20—H20	0.9300
C3—O2—C2	116.6 (2)	C11—C10—C13	121.0 (3)
N2—N1—C4	111.8 (2)	C9—C10—C13	122.1 (3)
N2—N1—C14	118.5 (2)	C12—C11—C10	122.0 (3)
C4—N1—C14	129.5 (2)	C12—C11—H11	119.0
C6—N2—N1	105.3 (2)	C10—C11—H11	119.0
C2—C1—H1A	109.5	C11—C12—C7	121.0 (3)
C2—C1—H1B	109.5	C11—C12—H12	119.5
H1A—C1—H1B	109.5	C7—C12—H12	119.5
C2—C1—H1C	109.5	C10—C13—H13A	109.5
H1A—C1—H1C	109.5	C10—C13—H13B	109.5
H1B—C1—H1C	109.5	H13A—C13—H13B	109.5
O2—C2—C1	106.8 (3)	C10—C13—H13C	109.5
O2—C2—H2A	110.4	H13A—C13—H13C	109.5
C1—C2—H2A	110.4	H13B—C13—H13C	109.5
O2—C2—H2B	110.4	N1—C14—C15	113.41 (19)
C1—C2—H2B	110.4	N1—C14—H14A	108.9
H2A—C2—H2B	108.6	C15—C14—H14A	108.9
O1—C3—O2	124.5 (3)	N1—C14—H14B	108.9
O1—C3—C4	125.5 (3)	C15—C14—H14B	108.9
O2—C3—C4	110.0 (2)	H14A—C14—H14B	107.7
N1—C4—C5	106.1 (2)	C20—C15—C16	118.7 (2)
N1—C4—C3	123.6 (2)	C20—C15—C14	121.2 (2)
C5—C4—C3	130.3 (3)	C16—C15—C14	119.9 (2)
C4—C5—C6	106.2 (2)	C17—C16—C15	120.7 (2)
C4—C5—H5	126.9	C17—C16—H16	119.7
C6—C5—H5	126.9	C15—C16—H16	119.7
N2—C6—C5	110.6 (2)	C18—C17—C16	119.9 (3)
N2—C6—C7	120.6 (2)	C18—C17—H17	120.0
C5—C6—C7	128.8 (2)	C16—C17—H17	120.0
C12—C7—C8	117.3 (2)	C17—C18—C19	120.6 (3)
C12—C7—C6	122.4 (2)	C17—C18—H18	119.7
C8—C7—C6	120.2 (2)	C19—C18—H18	119.7
C9—C8—C7	121.3 (3)	C18—C19—C20	119.7 (3)
C9—C8—H8	119.4	C18—C19—H19	120.1
C7—C8—H8	119.4	C20—C19—H19	120.1
C8—C9—C10	121.5 (3)	C19—C20—C15	120.3 (2)
C8—C9—H9	119.3	C19—C20—H20	119.9
C10—C9—H9	119.3	C15—C20—H20	119.9
C11—C10—C9	116.9 (3)
C4—N1—N2—C6	0.6 (3)	C12—C7—C8—C9	−0.2 (4)
C14—N1—N2—C6	176.1 (2)	C6—C7—C8—C9	179.8 (2)
C3—O2—C2—C1	−175.4 (3)	C7—C8—C9—C10	0.2 (5)
C2—O2—C3—O1	1.8 (4)	C8—C9—C10—C11	−0.4 (5)
C2—O2—C3—C4	−177.9 (2)	C8—C9—C10—C13	179.3 (3)
N2—N1—C4—C5	−0.6 (3)	C9—C10—C11—C12	0.6 (5)
C14—N1—C4—C5	−175.4 (2)	C13—C10—C11—C12	−179.1 (3)
N2—N1—C4—C3	−178.8 (2)	C10—C11—C12—C7	−0.7 (5)
C14—N1—C4—C3	6.4 (4)	C8—C7—C12—C11	0.4 (4)
O1—C3—C4—N1	5.4 (4)	C6—C7—C12—C11	−179.6 (3)
O2—C3—C4—N1	−174.9 (2)	N2—N1—C14—C15	−99.0 (3)
O1—C3—C4—C5	−172.3 (3)	C4—N1—C14—C15	75.5 (3)
O2—C3—C4—C5	7.4 (4)	N1—C14—C15—C20	42.9 (4)
N1—C4—C5—C6	0.4 (3)	N1—C14—C15—C16	−140.7 (3)
C3—C4—C5—C6	178.4 (2)	C20—C15—C16—C17	0.2 (4)
N1—N2—C6—C5	−0.4 (3)	C14—C15—C16—C17	−176.3 (3)
N1—N2—C6—C7	−179.9 (2)	C15—C16—C17—C18	−1.3 (5)
C4—C5—C6—N2	0.0 (3)	C16—C17—C18—C19	1.5 (5)
C4—C5—C6—C7	179.5 (2)	C17—C18—C19—C20	−0.6 (5)
N2—C6—C7—C12	−16.0 (4)	C18—C19—C20—C15	−0.5 (4)
C5—C6—C7—C12	164.6 (3)	C16—C15—C20—C19	0.7 (4)
N2—C6—C7—C8	164.0 (2)	C14—C15—C20—C19	177.2 (2)
C5—C6—C7—C8	−15.4 (4)