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

In the title mol-ecule, C(17)H(14)BrFN(2)O, the benzene rings form dihedral angles of 6.58 (6) and 85.31 (6)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0231 Å). The latter ring is planar with a maximum deviation of 0.032 (1) Å The dihedral angle between the benzene rings is 78.75 (6)°. In the crystal, weak C-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules into corrugated layers parallel to the ab plane.

Related literature

For our work on the synthesis of pyrazoline derivatives, see: Samshuddin et al. (2011 ▶). For related structures, see: Fun et al. (2010 ▶, 2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H14BrFN2O

M = 361.21

Monoclinic,

a = 6.0973 (5) Å

b = 12.3079 (11) Å

c = 20.1432 (16) Å

β = 96.700 (1)°

V = 1501.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.75 mm−1

T = 100 K

0.35 × 0.29 × 0.12 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.449, T max = 0.735

20560 measured reflections

5389 independent reflections

4508 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.064

S = 1.04

5389 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.25 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/S1600536812033351/cv5325sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033351/cv5325Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033351/cv5325Isup3.cml

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

C17H14BrFN2O	F(000) = 728
Mr = 361.21	Dx = 1.598 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7995 reflections
a = 6.0973 (5) Å	θ = 3.3–32.4°
b = 12.3079 (11) Å	µ = 2.75 mm−1
c = 20.1432 (16) Å	T = 100 K
β = 96.700 (1)°	Block, colourless
V = 1501.3 (2) Å3	0.35 × 0.29 × 0.12 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	5389 independent reflections
Radiation source: fine-focus sealed tube	4508 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 32.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.449, Tmax = 0.735	k = −18→18
20560 measured reflections	l = −30→28

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0284P)2 + 0.4844P] where P = (Fo2 + 2Fc2)/3
5389 reflections	(Δ/σ)max = 0.002
200 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.25 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
Br1	0.04341 (2)	0.791941 (11)	0.448115 (6)	0.02747 (5)
F1	−0.59388 (13)	1.16479 (7)	0.96048 (4)	0.02911 (17)
O1	0.64441 (14)	0.86820 (8)	0.74360 (4)	0.02269 (17)
N1	0.18952 (16)	0.95514 (8)	0.82286 (5)	0.01709 (17)
N2	0.33651 (16)	0.94281 (8)	0.77529 (5)	0.01819 (18)
C1	−0.12723 (19)	1.02079 (10)	0.90775 (6)	0.0197 (2)
H1A	−0.0275	0.9644	0.9231	0.024*
C2	−0.2902 (2)	1.05229 (10)	0.94636 (6)	0.0219 (2)
H2A	−0.3024	1.0189	0.9883	0.026*
C3	−0.43476 (19)	1.13377 (10)	0.92222 (6)	0.0198 (2)
C4	−0.42365 (19)	1.18535 (9)	0.86209 (6)	0.0198 (2)
H4A	−0.5265	1.2404	0.8468	0.024*
C5	−0.25649 (19)	1.15407 (9)	0.82441 (6)	0.0182 (2)
H5A	−0.2431	1.1896	0.7832	0.022*
C6	−0.10798 (18)	1.07118 (9)	0.84631 (5)	0.01613 (19)
C7	0.06512 (18)	1.03787 (9)	0.80585 (5)	0.01641 (19)
C8	0.1174 (2)	1.09452 (10)	0.74299 (6)	0.0204 (2)
H8A	0.1713	1.1694	0.7527	0.024*
H8B	−0.0138	1.0972	0.7091	0.024*
C9	0.30095 (19)	1.02199 (9)	0.71935 (6)	0.0182 (2)
H9A	0.4379	1.0659	0.7171	0.022*
C10	0.23654 (18)	0.96573 (9)	0.65297 (5)	0.01642 (19)
C11	0.38005 (19)	0.96669 (9)	0.60390 (6)	0.0182 (2)
H11A	0.5182	1.0028	0.6123	0.022*
C12	0.3230 (2)	0.91522 (10)	0.54268 (6)	0.0193 (2)
H12A	0.4217	0.9153	0.5095	0.023*
C13	0.1196 (2)	0.86390 (9)	0.53106 (6)	0.0188 (2)
C14	−0.02684 (19)	0.86179 (10)	0.57892 (6)	0.0204 (2)
H14A	−0.1656	0.8263	0.5701	0.025*
C15	0.03330 (19)	0.91257 (10)	0.64006 (6)	0.0193 (2)
H15A	−0.0648	0.9111	0.6734	0.023*
C16	0.50858 (18)	0.87211 (10)	0.78447 (6)	0.0179 (2)
C17	0.5186 (2)	0.79944 (10)	0.84496 (6)	0.0226 (2)
H17A	0.6488	0.7524	0.8465	0.034*
H17B	0.3851	0.7546	0.8422	0.034*
H17C	0.5285	0.8441	0.8855	0.034*

	U11	U22	U33	U12	U13	U23
Br1	0.03694 (8)	0.02603 (7)	0.01781 (6)	−0.00295 (5)	−0.00372 (4)	−0.00310 (5)
F1	0.0272 (4)	0.0295 (4)	0.0332 (4)	0.0103 (3)	0.0145 (3)	0.0057 (3)
O1	0.0178 (4)	0.0292 (4)	0.0216 (4)	−0.0003 (3)	0.0047 (3)	−0.0060 (3)
N1	0.0168 (4)	0.0200 (4)	0.0149 (4)	0.0013 (3)	0.0036 (3)	−0.0005 (3)
N2	0.0192 (4)	0.0214 (4)	0.0148 (4)	0.0026 (4)	0.0052 (3)	0.0007 (3)
C1	0.0195 (5)	0.0191 (5)	0.0207 (5)	0.0037 (4)	0.0036 (4)	0.0029 (4)
C2	0.0220 (5)	0.0230 (5)	0.0217 (5)	0.0041 (4)	0.0068 (4)	0.0055 (4)
C3	0.0177 (5)	0.0195 (5)	0.0230 (5)	0.0014 (4)	0.0060 (4)	−0.0011 (4)
C4	0.0199 (5)	0.0161 (5)	0.0228 (5)	0.0031 (4)	0.0001 (4)	−0.0005 (4)
C5	0.0214 (5)	0.0162 (5)	0.0165 (5)	0.0011 (4)	0.0003 (4)	0.0004 (4)
C6	0.0167 (5)	0.0150 (4)	0.0165 (5)	−0.0004 (4)	0.0009 (4)	−0.0020 (4)
C7	0.0177 (5)	0.0164 (5)	0.0151 (5)	−0.0006 (4)	0.0019 (4)	−0.0011 (4)
C8	0.0266 (6)	0.0180 (5)	0.0171 (5)	0.0026 (4)	0.0051 (4)	0.0010 (4)
C9	0.0207 (5)	0.0184 (5)	0.0160 (5)	−0.0013 (4)	0.0038 (4)	0.0004 (4)
C10	0.0178 (5)	0.0162 (5)	0.0157 (5)	−0.0008 (4)	0.0037 (4)	0.0015 (4)
C11	0.0182 (5)	0.0195 (5)	0.0174 (5)	−0.0039 (4)	0.0044 (4)	0.0008 (4)
C12	0.0229 (5)	0.0202 (5)	0.0155 (5)	−0.0018 (4)	0.0055 (4)	0.0018 (4)
C13	0.0229 (5)	0.0174 (5)	0.0155 (5)	−0.0004 (4)	−0.0007 (4)	0.0006 (4)
C14	0.0172 (5)	0.0206 (5)	0.0231 (5)	−0.0025 (4)	0.0008 (4)	0.0008 (4)
C15	0.0173 (5)	0.0215 (5)	0.0199 (5)	−0.0017 (4)	0.0055 (4)	0.0010 (4)
C16	0.0157 (5)	0.0204 (5)	0.0173 (5)	−0.0007 (4)	0.0003 (4)	−0.0046 (4)
C17	0.0241 (5)	0.0243 (5)	0.0191 (5)	0.0057 (4)	0.0008 (4)	0.0001 (4)

Br1—C13	1.9003 (11)	C8—C9	1.5494 (16)
F1—C3	1.3622 (14)	C8—H8A	0.9900
O1—C16	1.2349 (14)	C8—H8B	0.9900
N1—C7	1.2919 (14)	C9—C10	1.5163 (16)
N1—N2	1.3947 (13)	C9—H9A	1.0000
N2—C16	1.3590 (15)	C10—C11	1.3945 (16)
N2—C9	1.4864 (15)	C10—C15	1.3987 (16)
C1—C2	1.3866 (16)	C11—C12	1.3940 (16)
C1—C6	1.4013 (16)	C11—H11A	0.9500
C1—H1A	0.9500	C12—C13	1.3867 (17)
C2—C3	1.3853 (16)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.3887 (17)
C3—C4	1.3760 (17)	C14—C15	1.3916 (17)
C4—C5	1.3942 (17)	C14—H14A	0.9500
C4—H4A	0.9500	C15—H15A	0.9500
C5—C6	1.4008 (15)	C16—C17	1.5070 (17)
C5—H5A	0.9500	C17—H17A	0.9800
C6—C7	1.4653 (16)	C17—H17B	0.9800
C7—C8	1.5116 (16)	C17—H17C	0.9800
C7—N1—N2	107.94 (9)	N2—C9—C8	101.04 (9)
C16—N2—N1	121.60 (9)	C10—C9—C8	114.33 (10)
C16—N2—C9	124.40 (9)	N2—C9—H9A	109.8
N1—N2—C9	113.63 (9)	C10—C9—H9A	109.8
C2—C1—C6	120.72 (11)	C8—C9—H9A	109.8
C2—C1—H1A	119.6	C11—C10—C15	119.19 (10)
C6—C1—H1A	119.6	C11—C10—C9	120.12 (10)
C3—C2—C1	118.28 (11)	C15—C10—C9	120.69 (10)
C3—C2—H2A	120.9	C12—C11—C10	120.71 (11)
C1—C2—H2A	120.9	C12—C11—H11A	119.6
F1—C3—C4	118.69 (10)	C10—C11—H11A	119.6
F1—C3—C2	118.06 (11)	C13—C12—C11	118.83 (11)
C4—C3—C2	123.25 (11)	C13—C12—H12A	120.6
C3—C4—C5	117.78 (11)	C11—C12—H12A	120.6
C3—C4—H4A	121.1	C12—C13—C14	121.75 (11)
C5—C4—H4A	121.1	C12—C13—Br1	118.87 (9)
C4—C5—C6	121.09 (11)	C14—C13—Br1	119.37 (9)
C4—C5—H5A	119.5	C13—C14—C15	118.78 (11)
C6—C5—H5A	119.5	C13—C14—H14A	120.6
C5—C6—C1	118.87 (10)	C15—C14—H14A	120.6
C5—C6—C7	120.64 (10)	C14—C15—C10	120.73 (11)
C1—C6—C7	120.49 (10)	C14—C15—H15A	119.6
N1—C7—C6	120.77 (10)	C10—C15—H15A	119.6
N1—C7—C8	114.27 (10)	O1—C16—N2	120.09 (11)
C6—C7—C8	124.95 (10)	O1—C16—C17	123.28 (11)
C7—C8—C9	102.84 (9)	N2—C16—C17	116.61 (10)
C7—C8—H8A	111.2	C16—C17—H17A	109.5
C9—C8—H8A	111.2	C16—C17—H17B	109.5
C7—C8—H8B	111.2	H17A—C17—H17B	109.5
C9—C8—H8B	111.2	C16—C17—H17C	109.5
H8A—C8—H8B	109.1	H17A—C17—H17C	109.5
N2—C9—C10	111.65 (9)	H17B—C17—H17C	109.5
C7—N1—N2—C16	170.61 (10)	C16—N2—C9—C8	−168.23 (11)
C7—N1—N2—C9	−2.78 (13)	N1—N2—C9—C8	4.94 (12)
C6—C1—C2—C3	0.80 (19)	C7—C8—C9—N2	−4.85 (11)
C1—C2—C3—F1	−179.69 (11)	C7—C8—C9—C10	115.20 (10)
C1—C2—C3—C4	−0.44 (19)	N2—C9—C10—C11	−112.65 (12)
F1—C3—C4—C5	178.57 (10)	C8—C9—C10—C11	133.42 (11)
C2—C3—C4—C5	−0.67 (18)	N2—C9—C10—C15	67.46 (13)
C3—C4—C5—C6	1.44 (17)	C8—C9—C10—C15	−46.47 (15)
C4—C5—C6—C1	−1.10 (17)	C15—C10—C11—C12	−0.17 (17)
C4—C5—C6—C7	179.11 (11)	C9—C10—C11—C12	179.94 (10)
C2—C1—C6—C5	−0.05 (18)	C10—C11—C12—C13	0.69 (18)
C2—C1—C6—C7	179.74 (11)	C11—C12—C13—C14	−0.57 (18)
N2—N1—C7—C6	179.71 (10)	C11—C12—C13—Br1	−179.12 (9)
N2—N1—C7—C8	−0.93 (13)	C12—C13—C14—C15	−0.08 (18)
C5—C6—C7—N1	−173.72 (11)	Br1—C13—C14—C15	178.47 (9)
C1—C6—C7—N1	6.49 (17)	C13—C14—C15—C10	0.61 (18)
C5—C6—C7—C8	6.99 (17)	C11—C10—C15—C14	−0.49 (17)
C1—C6—C7—C8	−172.79 (11)	C9—C10—C15—C14	179.39 (11)
N1—C7—C8—C9	3.93 (13)	N1—N2—C16—O1	−175.15 (10)
C6—C7—C8—C9	−176.74 (10)	C9—N2—C16—O1	−2.50 (17)
C16—N2—C9—C10	69.83 (14)	N1—N2—C16—C17	6.25 (16)
N1—N2—C9—C10	−117.00 (10)	C9—N2—C16—C17	178.90 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1i	0.95	2.45	3.2772 (15)	146
C14—H14A···F1ii	0.95	2.50	3.3806 (15)	153
C15—H15A···O1iii	0.95	2.45	3.3800 (15)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1i	0.95	2.45	3.2772 (15)	146
C14—H14A⋯F1ii	0.95	2.50	3.3806 (15)	153
C15—H15A⋯O1iii	0.95	2.45	3.3800 (15)	166

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