1-Acetyl-5-(4-fluoro­phen­yl)-3-(4-nitro­phen­yl)-2-pyrazoline

Guo, H.-M.

doi:10.1107/S1600536807027833

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1-Acetyl-5-(4-fluorophenyl)-3-(4-nitrophenyl)-2-pyrazoline

H.-M. Guo

The title compound, C₁₇H₁₄FN₃O₃, was prepared by the reaction of hydrazine and 1-(4-nitrophenyl)-3-(4-fluorophenyl)-2-propenyl-1-ketone. The dihedral angle between the benzene ring bearing the nitro substituent and the pyrazoline ring is 3.82 (8)° and the dihedral angle between the two benzene rings is 70.27 (8)°. Weak intermolecular C—H

O hydrogen bonds are present in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027833/lh2419sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027833/lh2419Isup2.hkl Contains datablock I

CCDC reference: 654930

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R factor = 0.040
wR factor = 0.109
Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........          2
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........          1

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Pyrazoline and its derivatives are useful compounds found to possess antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. 1-Acetyl-3,5-diaryl-2-pyrazoline has been found to inhibit the monoamine oxidases (Manna et al., 2002). As part of our ongoing investgation of pyrazolines and their metal complexes, we report here the crystal strucutre of the title compound.

In the molecule (Fig. 1), all of the bond lengthes and bond angles fall in the normal ranges (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007). The dihedral angles formed by pyrazolinyl ring with phenyl groups at positions 3 and 5 of the pyrazoline are 3.82 (8) and 66.57 (8)°, respectively. Intermolecular C—H···O hydrogen bonds help stabilize the crystal structure of.

Related literature top

The medicinal and biological properties of pyrazoline derivatives has been reported previously (Rawal et al., 1963; Dhal et al., 1975; Lombardino & Ottemes, 1981; Manna et al., 2002). The bond lengths and angles of the title compound are similar to related structures (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007).

Experimental top

1-(p-Nitrophenyl)-3-(p-fluorophenyl)-2-propenyl-1-ketone (0.02 mol)and hydrazine (0.02 mol)were mixed in 99.5% acetic acid (40 ml) and stirred in refluxing for 6 h, then the mixture was poured into ice-water to afford a colourless solid. This solid was filtered and washed with water until the pH of the solution was ca 7.0. Finally, the solid was dry at room temperature. Single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from EtOH at room temperature.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXTL/PC.

Figures top

Fig. 1. The molecular structure and atom-labeling scheme with displacement ellipsoids drawn at the 30% probability level.

1-Acetyl-5-(4-fluorophenyl)-3-(4-nitrophenyl)-2-pyrazoline top

Crystal data top

C₁₇H₁₄FN₃O₃	F(000) = 680
M_r = 327.31	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3251 reflections
a = 5.7992 (11) Å	θ = 2.5–26.6°
b = 16.661 (3) Å	µ = 0.11 mm⁻¹
c = 16.056 (3) Å	T = 298 K
β = 99.387 (2)°	Bar, colourless
V = 1530.5 (5) Å³	0.50 × 0.25 × 0.21 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2326 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.5°, θ_min = 1.8°
φ and ω scans	h = −6→7
7736 measured reflections	k = −17→20
2826 independent reflections	l = −19→17

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.055P)² + 0.2585P] where P = (F_o² + 2F_c²)/3
2826 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₁₄FN₃O₃	V = 1530.5 (5) Å³
M_r = 327.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7992 (11) Å	µ = 0.11 mm⁻¹
b = 16.661 (3) Å	T = 298 K
c = 16.056 (3) Å	0.50 × 0.25 × 0.21 mm
β = 99.387 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2326 reflections with I > 2σ(I)
7736 measured reflections	R_int = 0.023
2826 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	Δρ_max = 0.18 e Å⁻³
2826 reflections	Δρ_min = −0.20 e Å⁻³
218 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1716 (3)	0.28095 (9)	0.31214 (10)	0.0497 (4)
H1	0.0514	0.2449	0.2940	0.060*
C2	0.1713 (3)	0.32338 (10)	0.38636 (10)	0.0576 (4)
H2	0.0515	0.3163	0.4178	0.069*
C3	0.3486 (3)	0.37541 (10)	0.41247 (10)	0.0591 (4)
C4	0.5251 (4)	0.38828 (12)	0.36756 (12)	0.0691 (5)
H4	0.6436	0.4248	0.3862	0.083*
C5	0.5239 (3)	0.34580 (11)	0.29357 (11)	0.0584 (4)
H5	0.6436	0.3538	0.2623	0.070*
C6	0.3472 (2)	0.29139 (8)	0.26500 (9)	0.0422 (3)
C7	0.3543 (3)	0.24768 (9)	0.18283 (9)	0.0459 (4)
H7	0.4945	0.2140	0.1882	0.055*
C8	0.3488 (3)	0.30551 (11)	0.10788 (9)	0.0525 (4)
H8A	0.3740	0.3606	0.1269	0.063*
H8B	0.4653	0.2911	0.0735	0.063*
C9	0.1069 (3)	0.29371 (9)	0.06089 (8)	0.0419 (3)
C10	−0.0012 (3)	0.34281 (8)	−0.01095 (8)	0.0392 (3)
C11	−0.2240 (3)	0.32545 (9)	−0.05429 (9)	0.0447 (4)
H11	−0.3050	0.2816	−0.0378	0.054*
C12	−0.3259 (3)	0.37190 (10)	−0.12099 (9)	0.0486 (4)
H12	−0.4751	0.3595	−0.1489	0.058*
C13	−0.2074 (3)	0.43700 (9)	−0.14678 (9)	0.0465 (4)
H13	−0.2756	0.4693	−0.1913	0.056*
C14	0.0134 (3)	0.45268 (8)	−0.10489 (8)	0.0401 (3)
C15	0.1209 (3)	0.40736 (8)	−0.03730 (8)	0.0398 (3)
H15	0.2709	0.4197	−0.0102	0.048*
C16	0.1205 (3)	0.12039 (10)	0.17533 (10)	0.0548 (4)
C17	−0.0864 (4)	0.07640 (11)	0.13026 (12)	0.0713 (6)
H17A	−0.0725	0.0708	0.0718	0.107*
H17B	−0.2260	0.1058	0.1350	0.107*
H17C	−0.0942	0.0242	0.1550	0.107*
F1	0.3487 (2)	0.41655 (7)	0.48573 (7)	0.0914 (4)
N1	0.1449 (2)	0.19873 (8)	0.15372 (7)	0.0490 (3)
N2	−0.0014 (2)	0.23332 (7)	0.08576 (7)	0.0466 (3)
N3	0.1435 (2)	0.52153 (7)	−0.13096 (8)	0.0483 (3)
O1	0.2651 (3)	0.09008 (7)	0.22967 (8)	0.0733 (4)
O2	0.3452 (2)	0.53098 (7)	−0.09699 (8)	0.0662 (4)
O3	0.0411 (2)	0.56620 (7)	−0.18506 (8)	0.0696 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0534 (10)	0.0437 (8)	0.0520 (9)	−0.0073 (7)	0.0088 (7)	0.0059 (7)
C2	0.0713 (12)	0.0525 (10)	0.0529 (9)	0.0023 (8)	0.0215 (8)	0.0073 (7)
C3	0.0758 (12)	0.0501 (10)	0.0496 (9)	0.0042 (9)	0.0046 (8)	−0.0025 (7)
C4	0.0653 (12)	0.0657 (12)	0.0723 (12)	−0.0146 (9)	−0.0012 (10)	−0.0138 (9)
C5	0.0499 (10)	0.0642 (11)	0.0617 (10)	−0.0105 (8)	0.0105 (8)	−0.0009 (8)
C6	0.0426 (8)	0.0395 (8)	0.0431 (8)	0.0004 (6)	0.0028 (6)	0.0096 (6)
C7	0.0446 (8)	0.0470 (8)	0.0459 (8)	−0.0014 (7)	0.0065 (7)	0.0067 (7)
C8	0.0512 (10)	0.0637 (10)	0.0430 (8)	−0.0079 (8)	0.0093 (7)	0.0111 (7)
C9	0.0494 (9)	0.0407 (8)	0.0371 (7)	−0.0017 (6)	0.0118 (6)	−0.0015 (6)
C10	0.0463 (8)	0.0379 (7)	0.0352 (7)	0.0011 (6)	0.0120 (6)	−0.0032 (6)
C11	0.0482 (9)	0.0427 (8)	0.0451 (8)	−0.0039 (6)	0.0129 (6)	−0.0024 (6)
C12	0.0442 (9)	0.0531 (9)	0.0474 (8)	−0.0013 (7)	0.0039 (7)	−0.0049 (7)
C13	0.0532 (9)	0.0457 (8)	0.0405 (8)	0.0081 (7)	0.0067 (7)	0.0014 (6)
C14	0.0500 (9)	0.0334 (7)	0.0387 (7)	0.0018 (6)	0.0126 (6)	−0.0026 (6)
C15	0.0436 (8)	0.0389 (7)	0.0376 (7)	−0.0006 (6)	0.0084 (6)	−0.0038 (6)
C16	0.0752 (12)	0.0448 (9)	0.0433 (8)	−0.0074 (8)	0.0062 (8)	0.0038 (7)
C17	0.0936 (15)	0.0519 (10)	0.0634 (11)	−0.0215 (10)	−0.0018 (10)	0.0059 (8)
F1	0.1220 (11)	0.0845 (8)	0.0669 (7)	0.0009 (7)	0.0134 (7)	−0.0266 (6)
N1	0.0603 (8)	0.0426 (7)	0.0417 (6)	−0.0075 (6)	0.0011 (6)	0.0059 (5)
N2	0.0562 (8)	0.0426 (7)	0.0399 (6)	−0.0049 (6)	0.0045 (6)	0.0026 (5)
N3	0.0611 (9)	0.0362 (7)	0.0501 (7)	0.0019 (6)	0.0164 (6)	0.0012 (6)
O1	0.0935 (10)	0.0537 (7)	0.0648 (8)	−0.0072 (6)	−0.0107 (7)	0.0180 (6)
O2	0.0631 (8)	0.0568 (7)	0.0771 (8)	−0.0177 (6)	0.0060 (7)	0.0093 (6)
O3	0.0817 (9)	0.0512 (7)	0.0761 (8)	0.0083 (6)	0.0138 (7)	0.0260 (6)

Geometric parameters (Å, º) top

C1—C6	1.375 (2)	C10—C15	1.391 (2)
C1—C2	1.386 (2)	C10—C11	1.394 (2)
C1—H1	0.9300	C11—C12	1.374 (2)
C2—C3	1.358 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.383 (2)
C3—F1	1.3613 (19)	C12—H12	0.9300
C3—C4	1.362 (3)	C13—C14	1.371 (2)
C4—C5	1.382 (2)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.3842 (19)
C5—C6	1.389 (2)	C14—N3	1.4709 (19)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.513 (2)	C16—O1	1.217 (2)
C7—N1	1.4745 (19)	C16—N1	1.364 (2)
C7—C8	1.538 (2)	C16—C17	1.489 (2)
C7—H7	0.9800	C17—H17A	0.9600
C8—C9	1.494 (2)	C17—H17B	0.9600
C8—H8A	0.9700	C17—H17C	0.9600
C8—H8B	0.9700	N1—N2	1.3930 (17)
C9—N2	1.2841 (18)	N3—O2	1.2176 (17)
C9—C10	1.4686 (19)	N3—O3	1.2219 (17)

C6—C1—C2	120.90 (15)	C15—C10—C9	119.73 (13)
C6—C1—H1	119.5	C11—C10—C9	121.26 (13)
C2—C1—H1	119.5	C12—C11—C10	121.21 (14)
C3—C2—C1	118.94 (16)	C12—C11—H11	119.4
C3—C2—H2	120.5	C10—C11—H11	119.4
C1—C2—H2	120.5	C11—C12—C13	120.20 (14)
C2—C3—F1	118.79 (17)	C11—C12—H12	119.9
C2—C3—C4	122.27 (16)	C13—C12—H12	119.9
F1—C3—C4	118.94 (17)	C14—C13—C12	118.20 (14)
C3—C4—C5	118.41 (17)	C14—C13—H13	120.9
C3—C4—H4	120.8	C12—C13—H13	120.9
C5—C4—H4	120.8	C13—C14—C15	123.10 (14)
C4—C5—C6	121.22 (16)	C13—C14—N3	119.37 (13)
C4—C5—H5	119.4	C15—C14—N3	117.51 (13)
C6—C5—H5	119.4	C14—C15—C10	118.25 (14)
C1—C6—C5	118.26 (14)	C14—C15—H15	120.9
C1—C6—C7	123.15 (14)	C10—C15—H15	120.9
C5—C6—C7	118.58 (13)	O1—C16—N1	119.46 (15)
N1—C7—C6	113.84 (12)	O1—C16—C17	123.41 (15)
N1—C7—C8	100.81 (11)	N1—C16—C17	117.13 (15)
C6—C7—C8	112.37 (13)	C16—C17—H17A	109.5
N1—C7—H7	109.8	C16—C17—H17B	109.5
C6—C7—H7	109.8	H17A—C17—H17B	109.5
C8—C7—H7	109.8	C16—C17—H17C	109.5
C9—C8—C7	102.17 (12)	H17A—C17—H17C	109.5
C9—C8—H8A	111.3	H17B—C17—H17C	109.5
C7—C8—H8A	111.3	C16—N1—N2	121.34 (13)
C9—C8—H8B	111.3	C16—N1—C7	124.25 (13)
C7—C8—H8B	111.3	N2—N1—C7	112.62 (11)
H8A—C8—H8B	109.2	C9—N2—N1	107.54 (12)
N2—C9—C10	120.84 (13)	O2—N3—O3	124.03 (14)
N2—C9—C8	114.40 (13)	O2—N3—C14	118.26 (13)
C10—C9—C8	124.69 (13)	O3—N3—C14	117.70 (14)
C15—C10—C11	119.01 (13)

C6—C1—C2—C3	−0.4 (2)	C10—C11—C12—C13	0.4 (2)
C1—C2—C3—F1	−179.51 (14)	C11—C12—C13—C14	0.9 (2)
C1—C2—C3—C4	1.0 (3)	C12—C13—C14—C15	−1.2 (2)
C2—C3—C4—C5	−0.9 (3)	C12—C13—C14—N3	180.00 (12)
F1—C3—C4—C5	179.60 (16)	C13—C14—C15—C10	0.1 (2)
C3—C4—C5—C6	0.3 (3)	N3—C14—C15—C10	178.97 (12)
C2—C1—C6—C5	−0.2 (2)	C11—C10—C15—C14	1.16 (19)
C2—C1—C6—C7	−179.00 (14)	C9—C10—C15—C14	−179.63 (12)
C4—C5—C6—C1	0.3 (2)	O1—C16—N1—N2	172.89 (15)
C4—C5—C6—C7	179.14 (16)	C17—C16—N1—N2	−7.4 (2)
C1—C6—C7—N1	5.5 (2)	O1—C16—N1—C7	9.3 (2)
C5—C6—C7—N1	−173.28 (14)	C17—C16—N1—C7	−170.99 (15)
C1—C6—C7—C8	119.32 (15)	C6—C7—N1—C16	−89.44 (18)
C5—C6—C7—C8	−59.47 (18)	C8—C7—N1—C16	150.03 (15)
N1—C7—C8—C9	14.43 (15)	C6—C7—N1—N2	105.70 (14)
C6—C7—C8—C9	−107.14 (14)	C8—C7—N1—N2	−14.83 (16)
C7—C8—C9—N2	−11.41 (17)	C10—C9—N2—N1	179.48 (12)
C7—C8—C9—C10	171.64 (13)	C8—C9—N2—N1	2.40 (17)
N2—C9—C10—C15	−179.24 (13)	C16—N1—N2—C9	−156.81 (14)
C8—C9—C10—C15	−2.5 (2)	C7—N1—N2—C9	8.55 (17)
N2—C9—C10—C11	−0.1 (2)	C13—C14—N3—O2	−174.83 (13)
C8—C9—C10—C11	176.70 (14)	C15—C14—N3—O2	6.29 (19)
C15—C10—C11—C12	−1.4 (2)	C13—C14—N3—O3	5.8 (2)
C9—C10—C11—C12	179.36 (12)	C15—C14—N3—O3	−173.06 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···02ⁱ	0.97	2.53	3.271 (2)	133
C12—H12···01ⁱⁱ	0.93	2.41	3.150 (2)	136

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄FN₃O₃
M_r	327.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	5.7992 (11), 16.661 (3), 16.056 (3)
β (°)	99.387 (2)
V (Å³)	1530.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.50 × 0.25 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7736, 2826, 2326
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.109, 1.05
No. of reflections	2826
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), SHELXTL/PC.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···02ⁱ	0.97	2.53	3.271 (2)	133
C12—H12···01ⁱⁱ	0.93	2.41	3.150 (2)	136

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, −y−1/2, z−3/2.

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