5-Ethyl-2-(4-fluoro-phen-yl)-4-phen-oxy-1H-pyrazol-3(2H)-one.

In the title compound, C(17)H(15)FN(2)O(2), the essentially planar pyrazole ring [maximum deviation = 0.026 (1) Å] makes dihedral angles of 72.06 (7) and 33.05 (7)°, with the phenyl and fluoro-benzene rings, respectively. The dihedral angle between the two six-membered rings is 87.88 (7)°. In the crystal, inter-molecular N-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules into layers lying parallel to the bc plane.

Related literature

For pyrazole derivatives and their microbial activity, see: Ragavan et al. (2009 ▶, 2010 ▶). For the synthesis, see: Ragavan et al. (2009 ▶). For related structures, see: Shahani et al. (2009 ▶, 2010a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H15FN2O2

M = 298.31

Monoclinic,

a = 15.332 (2) Å

b = 8.6833 (14) Å

c = 11.6066 (19) Å

β = 109.916 (3)°

V = 1452.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.55 × 0.14 × 0.08 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.947, T max = 0.992

12927 measured reflections

4247 independent reflections

3207 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.05

4247 reflections

204 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000754/hb5788sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000754/hb5788Isup2.hkl

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

C17H15FN2O2	F(000) = 624
Mr = 298.31	Dx = 1.364 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2971 reflections
a = 15.332 (2) Å	θ = 3.0–33.0°
b = 8.6833 (14) Å	µ = 0.10 mm−1
c = 11.6066 (19) Å	T = 100 K
β = 109.916 (3)°	Needle, colourless
V = 1452.8 (4) Å3	0.55 × 0.14 × 0.08 mm
Z = 4

Bruker APEXII DUO CCD diffractometer	4247 independent reflections
Radiation source: fine-focus sealed tube	3207 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 30.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→20
Tmin = 0.947, Tmax = 0.992	k = −12→9
12927 measured reflections	l = −16→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.047P)2 + 0.4776P] where P = (Fo2 + 2Fc2)/3
4247 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.77686 (5)	0.90535 (11)	0.09196 (7)	0.0332 (2)
O1	0.22938 (6)	0.55499 (11)	0.07275 (8)	0.0226 (2)
O2	0.40598 (6)	0.72722 (11)	0.20071 (7)	0.0243 (2)
N1	0.41488 (7)	0.72695 (13)	0.00442 (8)	0.0187 (2)
N2	0.36358 (7)	0.66422 (13)	−0.10812 (9)	0.0192 (2)
C1	0.55898 (8)	0.70430 (15)	−0.03872 (10)	0.0191 (2)
H1A	0.5320	0.6289	−0.0969	0.023*
C2	0.64946 (9)	0.75124 (16)	−0.01831 (11)	0.0215 (3)
H2A	0.6836	0.7098	−0.0634	0.026*
C3	0.68736 (8)	0.86072 (16)	0.07039 (11)	0.0222 (3)
C4	0.63952 (9)	0.92659 (15)	0.13937 (11)	0.0215 (3)
H4A	0.6677	0.9992	0.1994	0.026*
C5	0.54850 (8)	0.88198 (15)	0.11691 (10)	0.0200 (3)
H5A	0.5142	0.9261	0.1607	0.024*
C6	0.50869 (8)	0.77049 (14)	0.02820 (10)	0.0172 (2)
C7	0.37115 (8)	0.69697 (15)	0.08861 (10)	0.0187 (2)
C8	0.28708 (8)	0.62287 (15)	0.01905 (10)	0.0190 (2)
C9	0.28418 (8)	0.60586 (15)	−0.09962 (10)	0.0190 (2)
C10	0.14644 (8)	0.62813 (16)	0.06414 (11)	0.0204 (3)
C11	0.10224 (9)	0.56911 (18)	0.14043 (11)	0.0254 (3)
H11A	0.1284	0.4881	0.1933	0.030*
C12	0.01814 (10)	0.6329 (2)	0.13677 (13)	0.0337 (4)
H12A	−0.0120	0.5947	0.1880	0.040*
C13	−0.02094 (10)	0.7526 (2)	0.05755 (14)	0.0378 (4)
H13A	−0.0772	0.7950	0.0554	0.045*
C14	0.02428 (10)	0.8092 (2)	−0.01883 (13)	0.0330 (3)
H14A	−0.0023	0.8892	−0.0727	0.040*
C15	0.10888 (9)	0.74771 (17)	−0.01581 (11)	0.0252 (3)
H15A	0.1394	0.7863	−0.0665	0.030*
C16	0.21135 (9)	0.53400 (17)	−0.20637 (11)	0.0246 (3)
H16A	0.1673	0.6127	−0.2491	0.030*
H16B	0.1781	0.4578	−0.1764	0.030*
C17	0.25005 (10)	0.45693 (18)	−0.29685 (12)	0.0282 (3)
H17A	0.2009	0.4051	−0.3590	0.042*
H17B	0.2968	0.3836	−0.2542	0.042*
H17C	0.2769	0.5336	−0.3342	0.042*
H1N2	0.3689 (12)	0.706 (2)	−0.1764 (16)	0.035 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0199 (4)	0.0497 (6)	0.0311 (4)	−0.0092 (4)	0.0103 (3)	−0.0079 (4)
O1	0.0193 (4)	0.0301 (5)	0.0232 (4)	0.0039 (4)	0.0136 (3)	0.0076 (4)
O2	0.0251 (4)	0.0367 (6)	0.0138 (4)	0.0009 (4)	0.0100 (3)	−0.0019 (3)
N1	0.0179 (5)	0.0274 (6)	0.0124 (4)	−0.0018 (4)	0.0071 (4)	−0.0017 (4)
N2	0.0192 (5)	0.0275 (6)	0.0120 (4)	−0.0024 (4)	0.0067 (4)	−0.0009 (4)
C1	0.0208 (5)	0.0212 (6)	0.0166 (5)	0.0005 (5)	0.0080 (4)	−0.0013 (4)
C2	0.0211 (6)	0.0265 (7)	0.0200 (5)	0.0019 (5)	0.0109 (5)	−0.0001 (5)
C3	0.0179 (5)	0.0281 (7)	0.0202 (5)	−0.0016 (5)	0.0060 (4)	0.0021 (5)
C4	0.0220 (6)	0.0243 (6)	0.0174 (5)	−0.0009 (5)	0.0059 (4)	−0.0019 (4)
C5	0.0217 (6)	0.0237 (6)	0.0159 (5)	0.0031 (5)	0.0082 (4)	−0.0002 (4)
C6	0.0174 (5)	0.0209 (6)	0.0143 (5)	0.0013 (4)	0.0067 (4)	0.0027 (4)
C7	0.0203 (5)	0.0224 (6)	0.0160 (5)	0.0042 (5)	0.0097 (4)	0.0019 (4)
C8	0.0178 (5)	0.0244 (6)	0.0177 (5)	0.0016 (5)	0.0099 (4)	0.0023 (4)
C9	0.0181 (5)	0.0225 (6)	0.0177 (5)	0.0016 (5)	0.0078 (4)	0.0015 (4)
C10	0.0163 (5)	0.0283 (7)	0.0175 (5)	0.0002 (5)	0.0070 (4)	−0.0029 (4)
C11	0.0191 (6)	0.0394 (8)	0.0193 (6)	−0.0026 (5)	0.0087 (5)	0.0010 (5)
C12	0.0207 (6)	0.0588 (11)	0.0263 (6)	−0.0031 (7)	0.0142 (5)	−0.0045 (6)
C13	0.0218 (6)	0.0590 (11)	0.0344 (7)	0.0097 (7)	0.0119 (6)	−0.0071 (7)
C14	0.0295 (7)	0.0401 (9)	0.0288 (7)	0.0129 (6)	0.0090 (6)	0.0007 (6)
C15	0.0246 (6)	0.0314 (7)	0.0221 (6)	0.0039 (6)	0.0110 (5)	−0.0006 (5)
C16	0.0211 (6)	0.0321 (7)	0.0207 (6)	−0.0027 (5)	0.0071 (5)	−0.0019 (5)
C17	0.0301 (7)	0.0347 (8)	0.0194 (6)	−0.0042 (6)	0.0078 (5)	−0.0055 (5)

F1—C3	1.3644 (14)	C8—C9	1.3708 (16)
O1—C8	1.3763 (15)	C9—C16	1.4928 (17)
O1—C10	1.3941 (15)	C10—C15	1.3809 (18)
O2—C7	1.2544 (14)	C10—C11	1.3837 (18)
N1—C7	1.3851 (15)	C11—C12	1.3907 (19)
N1—N2	1.3862 (13)	C11—H11A	0.9300
N1—C6	1.4202 (16)	C12—C13	1.382 (2)
N2—C9	1.3529 (16)	C12—H12A	0.9300
N2—H1N2	0.899 (18)	C13—C14	1.388 (2)
C1—C2	1.3866 (17)	C13—H13A	0.9300
C1—C6	1.3915 (17)	C14—C15	1.3922 (19)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.3761 (18)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.5255 (19)
C3—C4	1.3806 (18)	C16—H16A	0.9700
C4—C5	1.3848 (17)	C16—H16B	0.9700
C4—H4A	0.9300	C17—H17A	0.9600
C5—C6	1.3934 (17)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C7—C8	1.4206 (17)
C8—O1—C10	118.93 (10)	N2—C9—C16	122.23 (11)
C7—N1—N2	109.59 (10)	C8—C9—C16	129.65 (12)
C7—N1—C6	127.91 (9)	C15—C10—C11	121.70 (12)
N2—N1—C6	119.98 (9)	C15—C10—O1	123.51 (11)
C9—N2—N1	108.32 (9)	C11—C10—O1	114.77 (11)
C9—N2—H1N2	124.6 (11)	C10—C11—C12	118.95 (13)
N1—N2—H1N2	118.8 (11)	C10—C11—H11A	120.5
C2—C1—C6	119.70 (11)	C12—C11—H11A	120.5
C2—C1—H1A	120.1	C13—C12—C11	120.48 (14)
C6—C1—H1A	120.1	C13—C12—H12A	119.8
C3—C2—C1	118.28 (12)	C11—C12—H12A	119.8
C3—C2—H2A	120.9	C12—C13—C14	119.58 (14)
C1—C2—H2A	120.9	C12—C13—H13A	120.2
F1—C3—C2	118.39 (12)	C14—C13—H13A	120.2
F1—C3—C4	118.40 (11)	C13—C14—C15	120.79 (14)
C2—C3—C4	123.20 (12)	C13—C14—H14A	119.6
C3—C4—C5	118.38 (12)	C15—C14—H14A	119.6
C3—C4—H4A	120.8	C10—C15—C14	118.50 (13)
C5—C4—H4A	120.8	C10—C15—H15A	120.8
C4—C5—C6	119.55 (11)	C14—C15—H15A	120.8
C4—C5—H5A	120.2	C9—C16—C17	113.48 (11)
C6—C5—H5A	120.2	C9—C16—H16A	108.9
C1—C6—C5	120.86 (11)	C17—C16—H16A	108.9
C1—C6—N1	119.90 (11)	C9—C16—H16B	108.9
C5—C6—N1	119.23 (11)	C17—C16—H16B	108.9
O2—C7—N1	123.71 (11)	H16A—C16—H16B	107.7
O2—C7—C8	131.88 (11)	C16—C17—H17A	109.5
N1—C7—C8	104.34 (10)	C16—C17—H17B	109.5
C9—C8—O1	127.09 (11)	H17A—C17—H17B	109.5
C9—C8—C7	109.42 (11)	C16—C17—H17C	109.5
O1—C8—C7	122.36 (10)	H17A—C17—H17C	109.5
N2—C9—C8	108.11 (10)	H17B—C17—H17C	109.5
C7—N1—N2—C9	4.94 (14)	O2—C7—C8—C9	−174.87 (14)
C6—N1—N2—C9	168.32 (11)	N1—C7—C8—C9	2.11 (14)
C6—C1—C2—C3	1.35 (18)	O2—C7—C8—O1	−6.2 (2)
C1—C2—C3—F1	179.00 (11)	N1—C7—C8—O1	170.74 (11)
C1—C2—C3—C4	−0.4 (2)	N1—N2—C9—C8	−3.48 (14)
F1—C3—C4—C5	179.60 (11)	N1—N2—C9—C16	177.94 (12)
C2—C3—C4—C5	−1.0 (2)	O1—C8—C9—N2	−167.13 (12)
C3—C4—C5—C6	1.43 (18)	C7—C8—C9—N2	0.83 (15)
C2—C1—C6—C5	−0.93 (18)	O1—C8—C9—C16	11.3 (2)
C2—C1—C6—N1	177.66 (11)	C7—C8—C9—C16	179.27 (13)
C4—C5—C6—C1	−0.49 (18)	C8—O1—C10—C15	13.96 (18)
C4—C5—C6—N1	−179.09 (11)	C8—O1—C10—C11	−167.62 (11)
C7—N1—C6—C1	137.38 (13)	C15—C10—C11—C12	−0.4 (2)
N2—N1—C6—C1	−22.65 (17)	O1—C10—C11—C12	−178.89 (12)
C7—N1—C6—C5	−44.01 (18)	C10—C11—C12—C13	0.4 (2)
N2—N1—C6—C5	155.96 (11)	C11—C12—C13—C14	0.1 (2)
N2—N1—C7—O2	173.06 (12)	C12—C13—C14—C15	−0.6 (2)
C6—N1—C7—O2	11.4 (2)	C11—C10—C15—C14	−0.1 (2)
N2—N1—C7—C8	−4.24 (13)	O1—C10—C15—C14	178.25 (12)
C6—N1—C7—C8	−165.94 (12)	C13—C14—C15—C10	0.6 (2)
C10—O1—C8—C9	−87.43 (16)	N2—C9—C16—C17	30.45 (18)
C10—O1—C8—C7	106.04 (13)	C8—C9—C16—C17	−147.80 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2i	0.899 (18)	1.803 (18)	2.6865 (14)	167.1 (16)
C11—H11A···F1ii	0.93	2.52	3.3441 (16)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2i	0.899 (18)	1.803 (18)	2.6865 (14)	167.1 (16)
C11—H11A⋯F1ii	0.93	2.52	3.3441 (16)	147

Symmetry codes: (i) ; (ii) .