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

In the title compound, C(19)H(17)FN(2)O(2), the pyrazole ring makes dihedral angles of 4.57 (16) and 81.19 (18)° with the fluoro-phenyl and benzene rings, respectively.

Related literature

For the applications of nitro­gen-containing heterocyclic compounds in agrochemical and pharmaceutical fields, see: Ge et al. (2009a ▶,b ▶). For related structures, see: Ge et al. (2007a ▶,b ▶).

Experimental

Crystal data

C19H17FN2O2

M = 324.35

Triclinic,

a = 8.119 (8) Å

b = 10.173 (6) Å

c = 10.814 (6) Å

α = 108.672 (15)°

β = 102.567 (16)°

γ = 91.460 (16)°

V = 821.5 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.21 × 0.16 × 0.12 mm

Data collection

Bruker SMART CD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.981, T max = 0.989

4034 measured reflections

2844 independent reflections

2014 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.245

S = 1.07

2844 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.30 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/S1600536811002340/jh2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002340/jh2256Isup2.hkl

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

C19H17FN2O2	Z = 2
Mr = 324.35	F(000) = 340
Triclinic, P1	Dx = 1.311 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.119 (8) Å	Cell parameters from 1645 reflections
b = 10.173 (6) Å	θ = 2.4–27.3°
c = 10.814 (6) Å	µ = 0.09 mm−1
α = 108.672 (15)°	T = 298 K
β = 102.567 (16)°	Block, white
γ = 91.460 (16)°	0.21 × 0.16 × 0.12 mm
V = 821.5 (10) Å3

Bruker SMART CD area-detector diffractometer	2844 independent reflections
Radiation source: fine-focus sealed tube	2014 reflections with I > 2σ(I)
graphite	Rint = 0.030
phi and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→6
Tmin = 0.981, Tmax = 0.989	k = −12→11
4034 measured reflections	l = −12→12

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.165P)2] where P = (Fo2 + 2Fc2)/3
2844 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.30 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
F1	0.0446 (3)	0.7940 (3)	1.0242 (2)	0.0941 (8)
O1	0.3457 (3)	0.4182 (3)	0.1271 (2)	0.0856 (8)
O2	0.3605 (2)	0.2792 (2)	0.2513 (2)	0.0633 (6)
N1	0.2763 (3)	0.6363 (2)	0.3527 (2)	0.0524 (6)
N2	0.2347 (3)	0.7094 (3)	0.4667 (2)	0.0544 (6)
C1	0.0891 (4)	0.7506 (4)	0.9042 (3)	0.0659 (9)
C2	0.1320 (4)	0.6187 (4)	0.8574 (3)	0.0681 (9)
H2	0.1317	0.5585	0.9063	0.082*
C3	0.1762 (4)	0.5763 (3)	0.7355 (3)	0.0604 (8)
H3	0.2066	0.4865	0.7023	0.072*
C4	0.1760 (3)	0.6651 (3)	0.6618 (3)	0.0486 (7)
C5	0.1315 (4)	0.7985 (3)	0.7127 (3)	0.0620 (8)
H5	0.1308	0.8594	0.6642	0.074*
C6	0.0878 (4)	0.8422 (4)	0.8360 (3)	0.0694 (9)
H6	0.0584	0.9321	0.8710	0.083*
C7	0.2232 (3)	0.6190 (3)	0.5320 (3)	0.0476 (7)
C8	0.2607 (3)	0.4883 (3)	0.4600 (3)	0.0507 (7)
H8	0.2623	0.4084	0.4842	0.061*
C9	0.2947 (3)	0.5017 (3)	0.3453 (3)	0.0496 (7)
C10	0.3367 (3)	0.3994 (3)	0.2303 (3)	0.0560 (8)
C11	0.3982 (4)	0.1676 (3)	0.1414 (3)	0.0707 (9)
H11A	0.5020	0.1943	0.1210	0.085*
H11B	0.3066	0.1471	0.0614	0.085*
C12	0.4175 (5)	0.0438 (4)	0.1851 (4)	0.0898 (12)
H12A	0.5120	0.0638	0.2615	0.135*
H12B	0.4370	−0.0338	0.1131	0.135*
H12C	0.3160	0.0211	0.2091	0.135*
C13	0.3159 (3)	0.7111 (3)	0.2662 (3)	0.0595 (8)
H13A	0.2573	0.7947	0.2804	0.071*
H13B	0.2741	0.6528	0.1730	0.071*
C14	0.5029 (3)	0.7517 (3)	0.2919 (3)	0.0532 (7)
C15	0.5833 (4)	0.7185 (3)	0.1874 (3)	0.0629 (8)
H15	0.5221	0.6684	0.1006	0.075*
C16	0.7528 (5)	0.7588 (4)	0.2109 (5)	0.0802 (11)
H16	0.8057	0.7374	0.1397	0.096*
C17	0.8439 (4)	0.8301 (4)	0.3378 (5)	0.0899 (13)
H17	0.9591	0.8567	0.3533	0.108*
C18	0.7659 (5)	0.8628 (4)	0.4434 (5)	0.0916 (12)
H18	0.8287	0.9107	0.5302	0.110*
C19	0.5959 (4)	0.8248 (4)	0.4209 (3)	0.0698 (9)
H19	0.5431	0.8480	0.4921	0.084*

	U11	U22	U33	U12	U13	U23
F1	0.0974 (14)	0.131 (2)	0.0598 (13)	0.0193 (13)	0.0397 (11)	0.0254 (13)
O1	0.126 (2)	0.0790 (17)	0.0587 (15)	0.0083 (14)	0.0397 (14)	0.0212 (13)
O2	0.0740 (13)	0.0592 (13)	0.0566 (13)	0.0104 (10)	0.0235 (10)	0.0135 (11)
N1	0.0546 (12)	0.0581 (15)	0.0503 (14)	0.0089 (10)	0.0189 (10)	0.0215 (12)
N2	0.0537 (12)	0.0584 (15)	0.0572 (15)	0.0104 (10)	0.0201 (11)	0.0225 (13)
C1	0.0529 (16)	0.092 (2)	0.0498 (18)	0.0047 (15)	0.0175 (13)	0.0157 (18)
C2	0.0730 (19)	0.081 (2)	0.055 (2)	0.0028 (16)	0.0184 (16)	0.0284 (18)
C3	0.0653 (17)	0.0633 (19)	0.0573 (18)	0.0065 (14)	0.0194 (14)	0.0233 (16)
C4	0.0415 (13)	0.0544 (16)	0.0481 (16)	0.0016 (11)	0.0106 (11)	0.0149 (14)
C5	0.0641 (17)	0.066 (2)	0.060 (2)	0.0139 (14)	0.0200 (14)	0.0230 (17)
C6	0.0698 (18)	0.074 (2)	0.064 (2)	0.0205 (16)	0.0261 (16)	0.0144 (19)
C7	0.0412 (12)	0.0525 (16)	0.0491 (16)	0.0030 (11)	0.0098 (11)	0.0178 (14)
C8	0.0479 (13)	0.0551 (18)	0.0507 (17)	0.0010 (11)	0.0126 (12)	0.0195 (14)
C9	0.0434 (13)	0.0542 (17)	0.0481 (16)	0.0010 (11)	0.0101 (11)	0.0137 (13)
C10	0.0517 (15)	0.0607 (19)	0.0514 (18)	−0.0028 (12)	0.0121 (13)	0.0137 (15)
C11	0.083 (2)	0.066 (2)	0.058 (2)	0.0123 (16)	0.0230 (16)	0.0080 (18)
C12	0.117 (3)	0.065 (2)	0.087 (3)	0.018 (2)	0.033 (2)	0.019 (2)
C13	0.0616 (16)	0.070 (2)	0.0578 (18)	0.0117 (14)	0.0170 (14)	0.0345 (16)
C14	0.0622 (15)	0.0529 (17)	0.0557 (18)	0.0109 (12)	0.0219 (13)	0.0278 (15)
C15	0.0761 (19)	0.0630 (19)	0.061 (2)	0.0124 (14)	0.0303 (16)	0.0270 (16)
C16	0.080 (2)	0.081 (2)	0.103 (3)	0.0177 (19)	0.048 (2)	0.045 (2)
C17	0.060 (2)	0.086 (3)	0.139 (4)	0.0027 (18)	0.028 (2)	0.057 (3)
C18	0.081 (2)	0.088 (3)	0.095 (3)	−0.0153 (19)	0.005 (2)	0.029 (2)
C19	0.078 (2)	0.073 (2)	0.056 (2)	−0.0005 (16)	0.0187 (16)	0.0186 (17)

F1—C1	1.362 (4)	C9—C10	1.456 (4)
O1—C10	1.208 (4)	C11—C12	1.480 (5)
O2—C10	1.325 (4)	C11—H11A	0.9700
O2—C11	1.451 (4)	C11—H11B	0.9700
N1—N2	1.340 (3)	C12—H12A	0.9600
N1—C9	1.360 (4)	C12—H12B	0.9600
N1—C13	1.460 (3)	C12—H12C	0.9600
N2—C7	1.339 (3)	C13—C14	1.504 (4)
C1—C2	1.358 (5)	C13—H13A	0.9700
C1—C6	1.360 (5)	C13—H13B	0.9700
C2—C3	1.379 (4)	C14—C15	1.380 (4)
C2—H2	0.9300	C14—C19	1.385 (4)
C3—C4	1.382 (4)	C15—C16	1.371 (5)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.382 (4)	C16—C17	1.360 (6)
C4—C7	1.470 (4)	C16—H16	0.9300
C5—C6	1.392 (4)	C17—C18	1.378 (6)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.372 (5)
C7—C8	1.388 (4)	C18—H18	0.9300
C8—C9	1.374 (4)	C19—H19	0.9300
C8—H8	0.9300
C10—O2—C11	116.1 (3)	O2—C11—H11A	110.3
N2—N1—C9	111.5 (2)	C12—C11—H11A	110.3
N2—N1—C13	118.3 (2)	O2—C11—H11B	110.3
C9—N1—C13	129.6 (2)	C12—C11—H11B	110.3
C7—N2—N1	105.6 (2)	H11A—C11—H11B	108.5
C2—C1—C6	122.8 (3)	C11—C12—H12A	109.5
C2—C1—F1	119.1 (3)	C11—C12—H12B	109.5
C6—C1—F1	118.1 (3)	H12A—C12—H12B	109.5
C1—C2—C3	118.4 (3)	C11—C12—H12C	109.5
C1—C2—H2	120.8	H12A—C12—H12C	109.5
C3—C2—H2	120.8	H12B—C12—H12C	109.5
C2—C3—C4	121.1 (3)	N1—C13—C14	112.9 (2)
C2—C3—H3	119.5	N1—C13—H13A	109.0
C4—C3—H3	119.5	C14—C13—H13A	109.0
C5—C4—C3	118.9 (3)	N1—C13—H13B	109.0
C5—C4—C7	120.4 (3)	C14—C13—H13B	109.0
C3—C4—C7	120.7 (3)	H13A—C13—H13B	107.8
C4—C5—C6	120.3 (3)	C15—C14—C19	119.2 (3)
C4—C5—H5	119.8	C15—C14—C13	120.6 (3)
C6—C5—H5	119.8	C19—C14—C13	120.1 (3)
C1—C6—C5	118.5 (3)	C16—C15—C14	120.3 (3)
C1—C6—H6	120.7	C16—C15—H15	119.8
C5—C6—H6	120.7	C14—C15—H15	119.8
N2—C7—C8	110.7 (2)	C17—C16—C15	120.3 (3)
N2—C7—C4	119.9 (2)	C17—C16—H16	119.9
C8—C7—C4	129.3 (3)	C15—C16—H16	119.9
C9—C8—C7	105.6 (3)	C16—C17—C18	120.1 (3)
C9—C8—H8	127.2	C16—C17—H17	120.0
C7—C8—H8	127.2	C18—C17—H17	120.0
N1—C9—C8	106.6 (2)	C19—C18—C17	120.2 (4)
N1—C9—C10	122.5 (3)	C19—C18—H18	119.9
C8—C9—C10	130.9 (3)	C17—C18—H18	119.9
O1—C10—O2	123.3 (3)	C18—C19—C14	119.9 (3)
O1—C10—C9	125.5 (3)	C18—C19—H19	120.1
O2—C10—C9	111.1 (3)	C14—C19—H19	120.1
O2—C11—C12	107.1 (3)
C9—N1—N2—C7	−1.2 (3)	C13—N1—C9—C10	−9.9 (4)
C13—N1—N2—C7	−173.5 (2)	C7—C8—C9—N1	−0.2 (3)
C6—C1—C2—C3	0.0 (5)	C7—C8—C9—C10	−177.9 (3)
F1—C1—C2—C3	179.8 (3)	C11—O2—C10—O1	−0.3 (4)
C1—C2—C3—C4	−0.4 (5)	C11—O2—C10—C9	178.2 (2)
C2—C3—C4—C5	0.4 (4)	N1—C9—C10—O1	−6.4 (4)
C2—C3—C4—C7	180.0 (3)	C8—C9—C10—O1	171.0 (3)
C3—C4—C5—C6	0.0 (4)	N1—C9—C10—O2	175.1 (2)
C7—C4—C5—C6	−179.6 (2)	C8—C9—C10—O2	−7.4 (4)
C2—C1—C6—C5	0.4 (5)	C10—O2—C11—C12	−179.2 (3)
F1—C1—C6—C5	−179.4 (3)	N2—N1—C13—C14	94.7 (3)
C4—C5—C6—C1	−0.4 (5)	C9—N1—C13—C14	−76.1 (4)
N1—N2—C7—C8	1.0 (3)	N1—C13—C14—C15	128.1 (3)
N1—N2—C7—C4	−178.9 (2)	N1—C13—C14—C19	−52.8 (4)
C5—C4—C7—N2	4.6 (4)	C19—C14—C15—C16	−0.8 (4)
C3—C4—C7—N2	−175.0 (2)	C13—C14—C15—C16	178.3 (3)
C5—C4—C7—C8	−175.3 (3)	C14—C15—C16—C17	1.1 (5)
C3—C4—C7—C8	5.0 (4)	C15—C16—C17—C18	−0.4 (6)
N2—C7—C8—C9	−0.5 (3)	C16—C17—C18—C19	−0.6 (6)
C4—C7—C8—C9	179.4 (2)	C17—C18—C19—C14	0.9 (6)
N2—N1—C9—C8	0.8 (3)	C15—C14—C19—C18	−0.2 (5)
C13—N1—C9—C8	172.1 (3)	C13—C14—C19—C18	−179.3 (3)
N2—N1—C9—C10	178.8 (2)