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

In the title compound, C(19)H(16)ClFN(2)O(2), the pyrazole ring makes dihedral angles of 5.15 (6) and 77.72 (6)°, with the fluoro-phenyl and chloro-phenyl rings, respectively.

Related literature

For the pharmacological activity of pyrazole compounds, see: Ge et al. (2007 ▶). For the synthesis of the title compound, see: Li et al. (2011 ▶). For the structure of ethyl 1-benzyl-3-(4-fluoro­phen­yl)-1H-pyrazole-5-carboxyl­ate, see: Han et al. (2011 ▶). For applications of nitro­gen-containing heterocyclic compounds, see: Ge et al. (2009 ▶, 2011 ▶).

Experimental

Crystal data

C19H16ClFN2O2

M = 358.79

Triclinic,

a = 8.267 (4) Å

b = 10.375 (5) Å

c = 11.368 (5) Å

α = 109.128 (7)°

β = 93.269 (7)°

γ = 104.842 (7)°

V = 879.8 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.22 × 0.14 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.949, T max = 0.974

4589 measured reflections

3091 independent reflections

2570 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.05

3091 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017156/fy2010sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017156/fy2010Isup2.hkl

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

C19H16ClFN2O2	Z = 2
Mr = 358.79	F(000) = 372
Triclinic, P1	Dx = 1.354 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.267 (4) Å	Cell parameters from 2637 reflections
b = 10.375 (5) Å	θ = 2.3–28.0°
c = 11.368 (5) Å	µ = 0.24 mm−1
α = 109.128 (7)°	T = 298 K
β = 93.269 (7)°	Block, colourless
γ = 104.842 (7)°	0.22 × 0.14 × 0.11 mm
V = 879.8 (7) Å3

Bruker SMART APEX CCD diffractometer	3091 independent reflections
Radiation source: fine-focus sealed tube	2570 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.949, Tmax = 0.974	k = −7→12
4589 measured reflections	l = −13→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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0578P)2 + 0.1997P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3091 reflections	Δρmax = 0.20 e Å−3
227 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.377 (15)

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
Cl1	1.50553 (8)	0.97753 (7)	0.28534 (7)	0.0902 (3)
F1	0.58679 (18)	0.70217 (16)	1.03659 (11)	0.0901 (4)
O1	0.8333 (2)	0.38223 (15)	0.13974 (12)	0.0730 (4)
O2	0.85036 (17)	0.24464 (14)	0.25387 (12)	0.0635 (4)
N1	0.76250 (18)	0.58191 (16)	0.36486 (13)	0.0520 (4)
N2	0.72669 (19)	0.64677 (16)	0.47978 (13)	0.0538 (4)
C1	1.2960 (3)	0.8828 (2)	0.28289 (19)	0.0623 (5)
C2	1.2032 (3)	0.7838 (2)	0.17127 (17)	0.0613 (5)
H2	1.2510	0.7663	0.0976	0.074*
C3	1.0381 (3)	0.7106 (2)	0.17021 (16)	0.0581 (5)
H3	0.9750	0.6430	0.0949	0.070*
C4	0.9639 (2)	0.73540 (19)	0.27895 (15)	0.0530 (4)
C5	1.0613 (3)	0.8359 (2)	0.39014 (17)	0.0665 (5)
H5	1.0142	0.8537	0.4641	0.080*
C6	1.2269 (3)	0.9101 (2)	0.39306 (19)	0.0735 (6)
H6	1.2910	0.9774	0.4681	0.088*
C7	0.7810 (2)	0.6583 (2)	0.27612 (17)	0.0589 (5)
H7A	0.7168	0.7269	0.2968	0.071*
H7B	0.7342	0.5910	0.1916	0.071*
C8	0.7893 (2)	0.45469 (18)	0.35425 (15)	0.0489 (4)
C9	0.7673 (2)	0.43606 (18)	0.46724 (15)	0.0502 (4)
H9	0.7764	0.3590	0.4890	0.060*
C10	0.7285 (2)	0.55756 (18)	0.54247 (15)	0.0480 (4)
C11	0.6912 (2)	0.59545 (18)	0.67292 (15)	0.0490 (4)
C12	0.7055 (2)	0.5107 (2)	0.74363 (17)	0.0599 (5)
H12	0.7390	0.4291	0.7082	0.072*
C13	0.6705 (3)	0.5465 (2)	0.86630 (18)	0.0663 (5)
H13	0.6798	0.4896	0.9133	0.080*
C14	0.6221 (2)	0.6670 (2)	0.91642 (17)	0.0633 (5)
C15	0.6065 (3)	0.7534 (2)	0.85037 (18)	0.0642 (5)
H15	0.5733	0.8349	0.8870	0.077*
C16	0.6412 (2)	0.7171 (2)	0.72777 (17)	0.0564 (4)
H16	0.6309	0.7747	0.6817	0.068*
C17	0.8260 (2)	0.35999 (19)	0.23761 (16)	0.0535 (4)
C18	0.8920 (3)	0.1438 (2)	0.1458 (2)	0.0723 (6)
H18A	0.9889	0.1920	0.1161	0.087*
H18B	0.7970	0.1014	0.0776	0.087*
C19	0.9320 (3)	0.0317 (3)	0.1868 (3)	0.0882 (7)
H19A	1.0243	0.0751	0.2555	0.132*
H19B	0.9631	−0.0351	0.1177	0.132*
H19C	0.8343	−0.0171	0.2136	0.132*

	U11	U22	U33	U12	U13	U23
Cl1	0.0733 (4)	0.0979 (5)	0.1037 (5)	0.0228 (3)	0.0231 (3)	0.0415 (4)
F1	0.1132 (10)	0.1118 (10)	0.0493 (7)	0.0361 (8)	0.0303 (6)	0.0283 (7)
O1	0.1059 (11)	0.0717 (9)	0.0482 (8)	0.0343 (8)	0.0217 (7)	0.0219 (7)
O2	0.0808 (9)	0.0592 (8)	0.0567 (8)	0.0294 (7)	0.0222 (6)	0.0198 (6)
N1	0.0610 (9)	0.0581 (9)	0.0442 (8)	0.0220 (7)	0.0137 (6)	0.0229 (7)
N2	0.0632 (9)	0.0583 (9)	0.0459 (8)	0.0234 (7)	0.0151 (6)	0.0206 (7)
C1	0.0701 (12)	0.0634 (11)	0.0642 (12)	0.0276 (9)	0.0183 (9)	0.0292 (10)
C2	0.0821 (13)	0.0669 (12)	0.0503 (10)	0.0354 (10)	0.0256 (9)	0.0277 (9)
C3	0.0814 (13)	0.0575 (10)	0.0414 (9)	0.0275 (9)	0.0134 (8)	0.0192 (8)
C4	0.0727 (11)	0.0539 (10)	0.0438 (9)	0.0274 (9)	0.0146 (8)	0.0240 (8)
C5	0.0851 (14)	0.0716 (13)	0.0418 (10)	0.0225 (11)	0.0198 (9)	0.0173 (9)
C6	0.0840 (15)	0.0748 (14)	0.0507 (11)	0.0163 (11)	0.0079 (10)	0.0139 (10)
C7	0.0733 (12)	0.0672 (11)	0.0492 (10)	0.0293 (9)	0.0124 (8)	0.0300 (9)
C8	0.0494 (9)	0.0522 (9)	0.0449 (9)	0.0146 (7)	0.0074 (7)	0.0171 (7)
C9	0.0546 (10)	0.0512 (9)	0.0475 (9)	0.0162 (8)	0.0088 (7)	0.0202 (8)
C10	0.0473 (9)	0.0538 (10)	0.0433 (9)	0.0134 (7)	0.0071 (7)	0.0188 (7)
C11	0.0463 (9)	0.0546 (10)	0.0445 (9)	0.0117 (7)	0.0068 (7)	0.0180 (8)
C12	0.0726 (12)	0.0609 (11)	0.0502 (10)	0.0217 (9)	0.0130 (8)	0.0225 (9)
C13	0.0807 (13)	0.0731 (13)	0.0521 (11)	0.0215 (11)	0.0138 (9)	0.0315 (10)
C14	0.0646 (11)	0.0799 (13)	0.0419 (9)	0.0145 (10)	0.0134 (8)	0.0212 (9)
C15	0.0692 (12)	0.0685 (12)	0.0543 (11)	0.0262 (10)	0.0157 (9)	0.0152 (9)
C16	0.0624 (11)	0.0623 (11)	0.0501 (10)	0.0222 (9)	0.0123 (8)	0.0236 (8)
C17	0.0549 (10)	0.0546 (10)	0.0478 (10)	0.0135 (8)	0.0097 (7)	0.0157 (8)
C18	0.0880 (14)	0.0623 (12)	0.0657 (12)	0.0312 (11)	0.0238 (10)	0.0125 (10)
C19	0.0947 (17)	0.0722 (14)	0.112 (2)	0.0396 (13)	0.0408 (14)	0.0357 (14)

Cl1—C1	1.753 (2)	C8—C9	1.375 (2)
F1—C14	1.363 (2)	C8—C17	1.470 (2)
O1—C17	1.210 (2)	C9—C10	1.398 (2)
O2—C17	1.331 (2)	C9—H9	0.9300
O2—C18	1.454 (2)	C10—C11	1.477 (2)
N1—N2	1.348 (2)	C11—C16	1.390 (3)
N1—C8	1.362 (2)	C11—C12	1.392 (2)
N1—C7	1.466 (2)	C12—C13	1.388 (3)
N2—C10	1.343 (2)	C12—H12	0.9300
C1—C2	1.373 (3)	C13—C14	1.366 (3)
C1—C6	1.381 (3)	C13—H13	0.9300
C2—C3	1.379 (3)	C14—C15	1.368 (3)
C2—H2	0.9300	C15—C16	1.387 (3)
C3—C4	1.389 (2)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.387 (3)	C18—C19	1.488 (3)
C4—C7	1.512 (3)	C18—H18A	0.9700
C5—C6	1.380 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—H7A	0.9700	C19—H19C	0.9600
C7—H7B	0.9700
C17—O2—C18	115.92 (15)	N2—C10—C11	119.71 (15)
N2—N1—C8	111.63 (13)	C9—C10—C11	129.52 (15)
N2—N1—C7	118.43 (15)	C16—C11—C12	118.60 (17)
C8—N1—C7	129.72 (15)	C16—C11—C10	120.50 (16)
C10—N2—N1	105.41 (14)	C12—C11—C10	120.90 (16)
C2—C1—C6	121.27 (19)	C13—C12—C11	120.85 (19)
C2—C1—Cl1	119.37 (15)	C13—C12—H12	119.6
C6—C1—Cl1	119.37 (17)	C11—C12—H12	119.6
C1—C2—C3	118.90 (17)	C14—C13—C12	118.54 (18)
C1—C2—H2	120.6	C14—C13—H13	120.7
C3—C2—H2	120.6	C12—C13—H13	120.7
C2—C3—C4	121.55 (17)	F1—C14—C13	118.73 (19)
C2—C3—H3	119.2	F1—C14—C15	118.72 (19)
C4—C3—H3	119.2	C13—C14—C15	122.55 (18)
C5—C4—C3	118.05 (18)	C14—C15—C16	118.70 (19)
C5—C4—C7	120.71 (16)	C14—C15—H15	120.6
C3—C4—C7	121.22 (16)	C16—C15—H15	120.6
C6—C5—C4	121.21 (18)	C15—C16—C11	120.75 (18)
C6—C5—H5	119.4	C15—C16—H16	119.6
C4—C5—H5	119.4	C11—C16—H16	119.6
C5—C6—C1	119.02 (19)	O1—C17—O2	124.03 (17)
C5—C6—H6	120.5	O1—C17—C8	125.40 (18)
C1—C6—H6	120.5	O2—C17—C8	110.57 (15)
N1—C7—C4	112.17 (14)	O2—C18—C19	107.60 (18)
N1—C7—H7A	109.2	O2—C18—H18A	110.2
C4—C7—H7A	109.2	C19—C18—H18A	110.2
N1—C7—H7B	109.2	O2—C18—H18B	110.2
C4—C7—H7B	109.2	C19—C18—H18B	110.2
H7A—C7—H7B	107.9	H18A—C18—H18B	108.5
N1—C8—C9	106.76 (15)	C18—C19—H19A	109.5
N1—C8—C17	122.96 (15)	C18—C19—H19B	109.5
C9—C8—C17	130.22 (17)	H19A—C19—H19B	109.5
C8—C9—C10	105.43 (15)	C18—C19—H19C	109.5
C8—C9—H9	127.3	H19A—C19—H19C	109.5
C10—C9—H9	127.3	H19B—C19—H19C	109.5
N2—C10—C9	110.77 (15)
C8—N1—N2—C10	−0.88 (18)	C8—C9—C10—N2	−0.08 (19)
C7—N1—N2—C10	−175.99 (14)	C8—C9—C10—C11	179.54 (16)
C6—C1—C2—C3	−0.1 (3)	N2—C10—C11—C16	5.1 (2)
Cl1—C1—C2—C3	−179.55 (14)	C9—C10—C11—C16	−174.51 (17)
C1—C2—C3—C4	0.3 (3)	N2—C10—C11—C12	−174.77 (16)
C2—C3—C4—C5	−0.5 (3)	C9—C10—C11—C12	5.6 (3)
C2—C3—C4—C7	177.88 (16)	C16—C11—C12—C13	0.1 (3)
C3—C4—C5—C6	0.4 (3)	C10—C11—C12—C13	179.94 (17)
C7—C4—C5—C6	−177.99 (18)	C11—C12—C13—C14	−0.2 (3)
C4—C5—C6—C1	−0.1 (3)	C12—C13—C14—F1	179.67 (17)
C2—C1—C6—C5	0.0 (3)	C12—C13—C14—C15	0.2 (3)
Cl1—C1—C6—C5	179.45 (16)	F1—C14—C15—C16	−179.51 (17)
N2—N1—C7—C4	95.64 (18)	C13—C14—C15—C16	0.0 (3)
C8—N1—C7—C4	−78.4 (2)	C14—C15—C16—C11	−0.1 (3)
C5—C4—C7—N1	−57.5 (2)	C12—C11—C16—C15	0.1 (3)
C3—C4—C7—N1	124.17 (18)	C10—C11—C16—C15	−179.79 (16)
N2—N1—C8—C9	0.85 (19)	C18—O2—C17—O1	1.5 (3)
C7—N1—C8—C9	175.25 (16)	C18—O2—C17—C8	−178.52 (16)
N2—N1—C8—C17	178.25 (15)	N1—C8—C17—O1	−1.4 (3)
C7—N1—C8—C17	−7.3 (3)	C9—C8—C17—O1	175.33 (19)
N1—C8—C9—C10	−0.45 (18)	N1—C8—C17—O2	178.63 (15)
C17—C8—C9—C10	−177.60 (17)	C9—C8—C17—O2	−4.6 (3)
N1—N2—C10—C9	0.57 (18)	C17—O2—C18—C19	174.11 (17)
N1—N2—C10—C11	−179.09 (14)