1-[3-(4-Fluoro-phen-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

In the title compound, C(17)H(15)FN(2)O, the pyrazoline ring adopts a flattened envelope conformation. The dihedral angle between the fluoro-substituted benzene ring and the phenyl ring is 69.20 (5)°. In the crystal, a pair of C-H⋯O hydrogen bonds link neighbouring mol-ecules, forming an inversion dimer. The crystal structure is further consolidated by C-H⋯π inter-actions and by a π-π inter-action with a centroid-centroid distance of 3.7379 (6) Å.

Related literature

For related structures, see: Fun et al. (2010 ▶, 2012a ▶,b ▶); Samshuddin et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H15FN2O

M = 282.31

Orthorhombic,

a = 13.0973 (6) Å

b = 8.6104 (4) Å

c = 24.5948 (12) Å

V = 2773.6 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.34 × 0.33 × 0.09 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.969, T max = 0.991

25040 measured reflections

4069 independent reflections

3442 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.03

4069 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.38 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 datablock(s) global, I. DOI: 10.1107/S1600536812033971/is5177sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033971/is5177Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033971/is5177Isup3.cml

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

C17H15FN2O	F(000) = 1184
Mr = 282.31	Dx = 1.352 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8833 reflections
a = 13.0973 (6) Å	θ = 3.0–30.1°
b = 8.6104 (4) Å	µ = 0.10 mm−1
c = 24.5948 (12) Å	T = 100 K
V = 2773.6 (2) Å3	Plate, colourless
Z = 8	0.34 × 0.33 × 0.09 mm

Bruker APEX DUO CCD area-detector diffractometer	4069 independent reflections
Radiation source: fine-focus sealed tube	3442 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 30.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→18
Tmin = 0.969, Tmax = 0.991	k = −9→12
25040 measured reflections	l = −34→34

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.9304P] where P = (Fo2 + 2Fc2)/3
4069 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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	0.82344 (6)	−0.34824 (9)	0.79260 (3)	0.03354 (18)
O1	0.34443 (6)	0.10960 (9)	0.53136 (3)	0.02267 (17)
N1	0.49592 (6)	−0.01792 (10)	0.64081 (4)	0.01708 (17)
N2	0.46304 (6)	0.06398 (10)	0.59506 (3)	0.01737 (17)
C1	0.76046 (8)	−0.09765 (12)	0.67970 (4)	0.0202 (2)
H1A	0.7939	−0.0381	0.6525	0.024*
C2	0.81782 (8)	−0.18030 (13)	0.71746 (5)	0.0246 (2)
H2A	0.8903	−0.1776	0.7165	0.029*
C3	0.76748 (9)	−0.26591 (13)	0.75618 (4)	0.0242 (2)
C4	0.66219 (9)	−0.27418 (13)	0.75934 (4)	0.0248 (2)
H4A	0.6297	−0.3347	0.7866	0.030*
C5	0.60547 (8)	−0.19140 (13)	0.72153 (4)	0.0223 (2)
H5A	0.5330	−0.1956	0.7228	0.027*
C6	0.65372 (8)	−0.10171 (11)	0.68153 (4)	0.01726 (19)
C7	0.59451 (7)	−0.01827 (11)	0.64033 (4)	0.01611 (18)
C8	0.64134 (7)	0.06184 (12)	0.59202 (4)	0.01745 (19)
H8A	0.6751	−0.0134	0.5675	0.021*
H8B	0.6916	0.1413	0.6035	0.021*
C9	0.54760 (7)	0.13688 (11)	0.56463 (4)	0.01575 (18)
H9A	0.5444	0.1043	0.5256	0.019*
C10	0.54856 (7)	0.31268 (11)	0.56813 (4)	0.01515 (18)
C11	0.49159 (7)	0.39548 (12)	0.60596 (4)	0.0186 (2)
H11A	0.4487	0.3420	0.6308	0.022*
C12	0.49747 (8)	0.55759 (13)	0.60740 (4)	0.0222 (2)
H12A	0.4590	0.6142	0.6335	0.027*
C13	0.55944 (8)	0.63580 (12)	0.57079 (4)	0.0220 (2)
H13A	0.5622	0.7460	0.5713	0.026*
C14	0.61750 (8)	0.55344 (12)	0.53337 (4)	0.0197 (2)
H14A	0.6605	0.6071	0.5086	0.024*
C15	0.61256 (7)	0.39232 (12)	0.53229 (4)	0.01723 (19)
H15A	0.6530	0.3359	0.5070	0.021*
C16	0.36726 (7)	0.04583 (12)	0.57425 (4)	0.01743 (19)
C17	0.29434 (8)	−0.05575 (13)	0.60548 (5)	0.0233 (2)
H17A	0.2245	−0.0367	0.5928	0.035*
H17B	0.2991	−0.0315	0.6443	0.035*
H17C	0.3120	−0.1651	0.5996	0.035*

	U11	U22	U33	U12	U13	U23
F1	0.0370 (4)	0.0359 (4)	0.0277 (4)	0.0095 (3)	−0.0118 (3)	0.0057 (3)
O1	0.0190 (4)	0.0253 (4)	0.0237 (4)	−0.0001 (3)	−0.0042 (3)	0.0026 (3)
N1	0.0155 (4)	0.0176 (4)	0.0182 (4)	0.0005 (3)	−0.0008 (3)	0.0014 (3)
N2	0.0127 (4)	0.0187 (4)	0.0207 (4)	−0.0015 (3)	−0.0006 (3)	0.0044 (3)
C1	0.0177 (5)	0.0205 (5)	0.0225 (5)	0.0007 (4)	−0.0028 (4)	−0.0006 (4)
C2	0.0196 (5)	0.0268 (5)	0.0273 (5)	0.0032 (4)	−0.0067 (4)	−0.0010 (4)
C3	0.0298 (6)	0.0226 (5)	0.0202 (5)	0.0072 (4)	−0.0084 (4)	−0.0021 (4)
C4	0.0293 (6)	0.0262 (5)	0.0190 (5)	0.0050 (4)	0.0012 (4)	0.0022 (4)
C5	0.0196 (5)	0.0262 (5)	0.0210 (5)	0.0035 (4)	0.0018 (4)	0.0021 (4)
C6	0.0165 (4)	0.0177 (4)	0.0176 (4)	0.0024 (3)	−0.0012 (3)	−0.0024 (3)
C7	0.0149 (4)	0.0153 (4)	0.0180 (4)	0.0007 (3)	0.0005 (3)	−0.0019 (3)
C8	0.0126 (4)	0.0180 (4)	0.0218 (5)	0.0006 (3)	0.0009 (3)	0.0015 (3)
C9	0.0122 (4)	0.0166 (4)	0.0184 (4)	−0.0010 (3)	0.0008 (3)	0.0009 (3)
C10	0.0123 (4)	0.0170 (4)	0.0161 (4)	0.0002 (3)	−0.0023 (3)	0.0004 (3)
C11	0.0153 (4)	0.0215 (5)	0.0189 (4)	0.0009 (3)	0.0008 (3)	0.0000 (4)
C12	0.0203 (5)	0.0223 (5)	0.0241 (5)	0.0034 (4)	−0.0008 (4)	−0.0055 (4)
C13	0.0219 (5)	0.0166 (4)	0.0275 (5)	−0.0005 (4)	−0.0054 (4)	−0.0019 (4)
C14	0.0160 (4)	0.0203 (5)	0.0230 (5)	−0.0035 (4)	−0.0028 (4)	0.0029 (4)
C15	0.0144 (4)	0.0196 (5)	0.0177 (4)	−0.0002 (3)	−0.0003 (3)	−0.0002 (3)
C16	0.0137 (4)	0.0168 (4)	0.0218 (4)	0.0000 (3)	−0.0003 (3)	−0.0020 (3)
C17	0.0149 (4)	0.0279 (5)	0.0271 (5)	−0.0053 (4)	0.0001 (4)	0.0016 (4)

F1—C3	1.3572 (12)	C8—H8A	0.9900
O1—C16	1.2261 (13)	C8—H8B	0.9900
N1—C7	1.2914 (13)	C9—C10	1.5162 (13)
N1—N2	1.3959 (11)	C9—H9A	1.0000
N2—C16	1.3639 (12)	C10—C11	1.3896 (13)
N2—C9	1.4767 (12)	C10—C15	1.3963 (13)
C1—C2	1.3903 (14)	C11—C12	1.3984 (15)
C1—C6	1.3991 (14)	C11—H11A	0.9500
C1—H1A	0.9500	C12—C13	1.3866 (15)
C2—C3	1.3729 (16)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.3886 (15)
C3—C4	1.3831 (16)	C13—H13A	0.9500
C4—C5	1.3875 (15)	C14—C15	1.3891 (14)
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.4012 (14)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C17	1.5058 (14)
C6—C7	1.4644 (13)	C17—H17A	0.9800
C7—C8	1.5045 (14)	C17—H17B	0.9800
C8—C9	1.5422 (13)	C17—H17C	0.9800
C7—N1—N2	107.59 (8)	N2—C9—C8	101.40 (7)
C16—N2—N1	121.90 (8)	C10—C9—C8	112.76 (8)
C16—N2—C9	123.25 (8)	N2—C9—H9A	109.6
N1—N2—C9	113.07 (8)	C10—C9—H9A	109.6
C2—C1—C6	120.37 (10)	C8—C9—H9A	109.6
C2—C1—H1A	119.8	C11—C10—C15	119.55 (9)
C6—C1—H1A	119.8	C11—C10—C9	123.07 (9)
C3—C2—C1	118.60 (10)	C15—C10—C9	117.35 (8)
C3—C2—H2A	120.7	C10—C11—C12	119.96 (9)
C1—C2—H2A	120.7	C10—C11—H11A	120.0
F1—C3—C2	118.61 (10)	C12—C11—H11A	120.0
F1—C3—C4	118.32 (10)	C13—C12—C11	120.04 (10)
C2—C3—C4	123.06 (10)	C13—C12—H12A	120.0
C3—C4—C5	118.02 (10)	C11—C12—H12A	120.0
C3—C4—H4A	121.0	C12—C13—C14	120.19 (10)
C5—C4—H4A	121.0	C12—C13—H13A	119.9
C4—C5—C6	120.81 (10)	C14—C13—H13A	119.9
C4—C5—H5A	119.6	C13—C14—C15	119.82 (10)
C6—C5—H5A	119.6	C13—C14—H14A	120.1
C1—C6—C5	119.14 (9)	C15—C14—H14A	120.1
C1—C6—C7	119.65 (9)	C14—C15—C10	120.42 (9)
C5—C6—C7	121.15 (9)	C14—C15—H15A	119.8
N1—C7—C6	121.63 (9)	C10—C15—H15A	119.8
N1—C7—C8	114.44 (9)	O1—C16—N2	119.73 (9)
C6—C7—C8	123.74 (9)	O1—C16—C17	122.97 (9)
C7—C8—C9	102.27 (8)	N2—C16—C17	117.29 (9)
C7—C8—H8A	111.3	C16—C17—H17A	109.5
C9—C8—H8A	111.3	C16—C17—H17B	109.5
C7—C8—H8B	111.3	H17A—C17—H17B	109.5
C9—C8—H8B	111.3	C16—C17—H17C	109.5
H8A—C8—H8B	109.2	H17A—C17—H17C	109.5
N2—C9—C10	113.69 (8)	H17B—C17—H17C	109.5
C7—N1—N2—C16	159.15 (9)	N1—N2—C9—C10	−110.76 (9)
C7—N1—N2—C9	−6.08 (11)	C16—N2—C9—C8	−154.47 (9)
C6—C1—C2—C3	0.25 (16)	N1—N2—C9—C8	10.53 (10)
C1—C2—C3—F1	179.15 (9)	C7—C8—C9—N2	−10.18 (9)
C1—C2—C3—C4	0.17 (17)	C7—C8—C9—C10	111.76 (9)
F1—C3—C4—C5	−179.15 (10)	N2—C9—C10—C11	14.38 (13)
C2—C3—C4—C5	−0.16 (17)	C8—C9—C10—C11	−100.34 (10)
C3—C4—C5—C6	−0.26 (16)	N2—C9—C10—C15	−167.56 (8)
C2—C1—C6—C5	−0.66 (15)	C8—C9—C10—C15	77.72 (11)
C2—C1—C6—C7	−177.92 (9)	C15—C10—C11—C12	0.96 (14)
C4—C5—C6—C1	0.67 (16)	C9—C10—C11—C12	178.98 (9)
C4—C5—C6—C7	177.89 (10)	C10—C11—C12—C13	0.55 (15)
N2—N1—C7—C6	−176.87 (8)	C11—C12—C13—C14	−1.38 (16)
N2—N1—C7—C8	−1.65 (11)	C12—C13—C14—C15	0.69 (15)
C1—C6—C7—N1	−179.40 (9)	C13—C14—C15—C10	0.84 (15)
C5—C6—C7—N1	3.40 (15)	C11—C10—C15—C14	−1.66 (14)
C1—C6—C7—C8	5.84 (15)	C9—C10—C15—C14	−179.79 (9)
C5—C6—C7—C8	−171.37 (9)	N1—N2—C16—O1	−173.68 (9)
N1—C7—C8—C9	8.00 (11)	C9—N2—C16—O1	−9.96 (15)
C6—C7—C8—C9	−176.89 (9)	N1—N2—C16—C17	5.37 (14)
C16—N2—C9—C10	84.23 (11)	C9—N2—C16—C17	169.09 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.99	2.58	3.3797 (13)	138
C1—H1A···Cg2ii	0.95	2.85	3.6856 (11)	148
C13—H13A···Cg1iii	0.95	2.73	3.6370 (11)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the pyrazole N1/N2/C7–C9 ring and the phenyl C10–C15 ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.99	2.58	3.3797 (13)	138
C1—H1A⋯Cg2ii	0.95	2.85	3.6856 (11)	148
C13—H13A⋯Cg1iii	0.95	2.73	3.6370 (11)	161

Symmetry codes: (i) ; (ii) ; (iii) .