5-(p-Fluoro­phen­yl)-1,3-diphenyl-2-pyraz­oline

The title compound, C₂₁H₁₇FN₂, was prepared from phenyl­hydrazine and 1-phenyl-3-(p-fluoro­phen­yl)-2-propenyl-1-ketone. The pyrazolinyl ring forms dihedral angles of 11.87 (12), 8.30 (12) and 65.89 (12)° with phenyl rings at the 1 and 3 positions and the fluoro­phenyl ring, respectively.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.101
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     -   C8      ..       5.52 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C9     = ...          R

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

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S1. Comment

As important and useful five-membered heterocyclic compounds, pyrazoline and its derivatives were found to possess antiviral (Rawal et al. 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino et al.,1981) activities. Several 1,3,5-triaryl-2-pyrazolines were also used as scintillation solutes (Wiley et al.,1958). Here, we report the crystal strucutre of the title compound (I).

In the structure of (I) (Fig. 1), all of the bond lengths and bond angles fall in the normal range (Rurack et al., 2000; Fahrni et al., 2003; Guo et al., 2006). The mean plane of pyrazolinyl ring N1/N2/C7—C9 make dihedral angles of 11.87 (12), 8.30 (12) and 65.89 (12)°, with the benzene rings C16—C21, C1—C6 and C10—C15 respectively.

Related literature

For related literature, see: Dhal et al. (1975); Fahrni et al. (2003); Guo et al. (2006); Lombardino & Ottemes (1981); Orzeszka et al. (2000); Rawal et al. (1963); Rurack et al. (2000); Wiley et al. (1958).

S2. Experimental

1-Phenyl-3-(p-fluorophenyl)-2-propenyl-1-ketone (0.02 mol) and phenylhydrazine (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 yellow solids. The solids were filtrated and washed with water until the pH of solution is about to 7.0. Finally, the red solid crystals were dried under room temperature. Single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from EtOH at room temperature.

S3. Refinement

H atoms were fixed geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.98 Å, and with U_iso=1.2–1.5U_eq of the parent atoms.

Computing details

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 (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

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

5-(p-Fluorophenyl)-1,3-diphenyl-2-pyrazoline

Crystal data

C21H17FN2	F(000) = 664
Mr = 316.37	Dx = 1.250 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1142 reflections
a = 11.476 (5) Å	θ = 2.4–20.0°
b = 13.389 (5) Å	µ = 0.08 mm^−1
c = 11.774 (4) Å	T = 294 K
β = 111.653 (6)°	Bar, yellow
V = 1681.4 (11) Å^3	0.22 × 0.20 × 0.14 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2958 independent reflections
Radiation source: fine-focus sealed tube	1473 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→13
Tmin = 0.982, Tmax = 0.989	k = −7→15
7071 measured reflections	l = −14→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0343P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2958 reflections	Δρmax = 0.12 e Å^−3
218 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0084 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.10006 (15)	0.46529 (10)	0.77127 (14)	0.1173 (6)
N1	0.29414 (16)	−0.06861 (13)	0.87003 (15)	0.0592 (5)
N2	0.33402 (16)	0.02657 (13)	0.85440 (15)	0.0621 (5)
C1	0.2031 (2)	−0.24652 (19)	0.9413 (2)	0.0727 (7)
H1	0.2442	−0.2529	0.8868	0.087*
C2	0.1559 (3)	−0.3302 (2)	0.9768 (3)	0.0946 (9)
H2	0.1651	−0.3925	0.9461	0.113*
C3	0.0953 (2)	−0.3221 (2)	1.0573 (3)	0.0904 (8)
H3	0.0643	−0.3789	1.0819	0.108*
C4	0.0806 (2)	−0.2304 (2)	1.1013 (2)	0.0783 (7)
H4	0.0383	−0.2245	1.1548	0.094*
C5	0.1288 (2)	−0.14629 (18)	1.06592 (19)	0.0643 (6)
H5	0.1196	−0.0841	1.0968	0.077*
C6	0.19058 (19)	−0.15360 (17)	0.98517 (18)	0.0534 (6)
C7	0.24386 (19)	−0.06540 (16)	0.95107 (18)	0.0522 (6)
C8	0.2448 (2)	0.03719 (15)	1.00217 (19)	0.0651 (6)
H8A	0.2823	0.0368	1.0907	0.078*
H8B	0.1607	0.0643	0.9769	0.078*
C9	0.3251 (2)	0.09683 (15)	0.94696 (18)	0.0557 (6)
H9	0.4086	0.1076	1.0094	0.067*
C10	0.26740 (18)	0.19610 (15)	0.89596 (19)	0.0485 (5)
C11	0.2857 (2)	0.27606 (18)	0.9737 (2)	0.0626 (6)
H11	0.3369	0.2688	1.0555	0.075*
C12	0.2297 (2)	0.36675 (18)	0.9326 (3)	0.0768 (7)
H12	0.2416	0.4205	0.9857	0.092*
C13	0.1567 (2)	0.37566 (19)	0.8128 (3)	0.0705 (7)
C14	0.1370 (2)	0.2999 (2)	0.7326 (2)	0.0673 (7)
H14	0.0870	0.3085	0.6507	0.081*
C15	0.1930 (2)	0.20892 (16)	0.7753 (2)	0.0597 (6)
H15	0.1801	0.1556	0.7213	0.072*
C16	0.41798 (19)	0.03619 (17)	0.79499 (18)	0.0553 (6)
C17	0.4340 (2)	−0.04195 (18)	0.72432 (19)	0.0665 (6)
H17	0.3910	−0.1017	0.7191	0.080*
C18	0.5140 (2)	−0.0304 (2)	0.6621 (2)	0.0785 (7)
H18	0.5244	−0.0828	0.6149	0.094*
C19	0.5786 (2)	0.0571 (2)	0.6685 (2)	0.0803 (8)
H19	0.6327	0.0638	0.6265	0.096*
C20	0.5625 (2)	0.1340 (2)	0.7375 (2)	0.0722 (7)
H20	0.6055	0.1936	0.7417	0.087*
C21	0.4835 (2)	0.12442 (17)	0.80117 (19)	0.0629 (6)
H21	0.4740	0.1772	0.8483	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1337 (13)	0.0680 (10)	0.1532 (14)	0.0224 (9)	0.0564 (11)	0.0353 (9)
N1	0.0616 (12)	0.0649 (13)	0.0596 (12)	0.0006 (10)	0.0325 (10)	−0.0002 (10)
N2	0.0717 (13)	0.0592 (12)	0.0714 (13)	0.0028 (10)	0.0450 (11)	−0.0017 (10)
C1	0.0777 (17)	0.0666 (17)	0.0866 (18)	0.0077 (14)	0.0454 (14)	0.0027 (15)
C2	0.101 (2)	0.0677 (19)	0.131 (3)	0.0109 (16)	0.062 (2)	0.0078 (17)
C3	0.082 (2)	0.086 (2)	0.113 (2)	0.0033 (16)	0.0477 (18)	0.0298 (18)
C4	0.0665 (16)	0.105 (2)	0.0722 (18)	−0.0017 (17)	0.0361 (14)	0.0099 (17)
C5	0.0588 (15)	0.0812 (18)	0.0568 (15)	−0.0060 (13)	0.0260 (13)	−0.0024 (13)
C6	0.0482 (13)	0.0652 (16)	0.0483 (14)	0.0054 (12)	0.0195 (11)	0.0047 (12)
C7	0.0497 (13)	0.0618 (16)	0.0462 (14)	0.0077 (12)	0.0190 (11)	0.0014 (12)
C8	0.0764 (16)	0.0677 (16)	0.0607 (15)	0.0142 (13)	0.0363 (13)	0.0108 (12)
C9	0.0563 (14)	0.0638 (15)	0.0474 (13)	0.0064 (12)	0.0197 (11)	−0.0004 (12)
C10	0.0442 (12)	0.0570 (15)	0.0443 (14)	−0.0027 (11)	0.0166 (11)	−0.0015 (12)
C11	0.0667 (15)	0.0632 (16)	0.0565 (15)	−0.0087 (13)	0.0210 (12)	−0.0052 (14)
C12	0.094 (2)	0.0542 (18)	0.088 (2)	−0.0121 (15)	0.0406 (17)	−0.0085 (15)
C13	0.0725 (18)	0.0514 (18)	0.095 (2)	0.0055 (14)	0.0396 (17)	0.0217 (17)
C14	0.0584 (15)	0.0815 (19)	0.0596 (17)	0.0032 (14)	0.0188 (13)	0.0134 (16)
C15	0.0573 (14)	0.0686 (17)	0.0514 (16)	0.0008 (13)	0.0179 (12)	−0.0053 (12)
C16	0.0490 (14)	0.0703 (17)	0.0505 (14)	0.0131 (13)	0.0228 (12)	0.0117 (12)
C17	0.0650 (16)	0.0815 (17)	0.0618 (15)	0.0022 (13)	0.0338 (13)	−0.0002 (13)
C18	0.0783 (18)	0.101 (2)	0.0682 (17)	0.0033 (16)	0.0412 (15)	−0.0076 (15)
C19	0.0631 (17)	0.118 (2)	0.0707 (18)	0.0049 (17)	0.0369 (14)	0.0097 (17)
C20	0.0483 (15)	0.094 (2)	0.0768 (18)	0.0042 (14)	0.0261 (14)	0.0210 (15)
C21	0.0526 (15)	0.0739 (18)	0.0638 (16)	0.0085 (13)	0.0233 (12)	0.0097 (12)

Geometric parameters (Å, º)

F1—C13	1.367 (2)	C9—H9	0.9800
N1—C7	1.285 (2)	C10—C15	1.372 (2)
N1—N2	1.389 (2)	C10—C11	1.373 (3)
N2—C16	1.390 (2)	C11—C12	1.376 (3)
N2—C9	1.472 (2)	C11—H11	0.9300
C1—C6	1.375 (3)	C12—C13	1.354 (3)
C1—C2	1.375 (3)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.347 (3)
C2—C3	1.372 (3)	C14—C15	1.382 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.367 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C21	1.387 (3)
C4—C5	1.385 (3)	C16—C17	1.391 (3)
C4—H4	0.9300	C17—C18	1.378 (3)
C5—C6	1.383 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.373 (3)
C6—C7	1.453 (3)	C18—H18	0.9300
C7—C8	1.498 (2)	C19—C20	1.366 (3)
C8—C9	1.533 (3)	C19—H19	0.9300
C8—H8A	0.9700	C20—C21	1.379 (3)
C8—H8B	0.9700	C20—H20	0.9300
C9—C10	1.507 (3)	C21—H21	0.9300
C7—N1—N2	109.14 (17)	C15—C10—C11	118.4 (2)
N1—N2—C16	118.38 (18)	C15—C10—C9	122.46 (19)
N1—N2—C9	111.83 (16)	C11—C10—C9	119.0 (2)
C16—N2—C9	124.35 (19)	C10—C11—C12	121.2 (2)
C6—C1—C2	121.1 (2)	C10—C11—H11	119.4
C6—C1—H1	119.5	C12—C11—H11	119.4
C2—C1—H1	119.5	C13—C12—C11	118.2 (2)
C3—C2—C1	120.2 (3)	C13—C12—H12	120.9
C3—C2—H2	119.9	C11—C12—H12	120.9
C1—C2—H2	119.9	C14—C13—C12	122.9 (2)
C4—C3—C2	119.9 (2)	C14—C13—F1	118.4 (3)
C4—C3—H3	120.1	C12—C13—F1	118.7 (3)
C2—C3—H3	120.1	C13—C14—C15	118.3 (2)
C3—C4—C5	119.8 (2)	C13—C14—H14	120.9
C3—C4—H4	120.1	C15—C14—H14	120.9
C5—C4—H4	120.1	C10—C15—C14	121.0 (2)
C6—C5—C4	120.8 (2)	C10—C15—H15	119.5
C6—C5—H5	119.6	C14—C15—H15	119.5
C4—C5—H5	119.6	C21—C16—N2	121.0 (2)
C1—C6—C5	118.2 (2)	C21—C16—C17	118.9 (2)
C1—C6—C7	121.3 (2)	N2—C16—C17	120.0 (2)
C5—C6—C7	120.5 (2)	C18—C17—C16	119.6 (2)
N1—C7—C6	121.9 (2)	C18—C17—H17	120.2
N1—C7—C8	112.96 (19)	C16—C17—H17	120.2
C6—C7—C8	125.16 (19)	C19—C18—C17	121.2 (2)
C7—C8—C9	102.93 (17)	C19—C18—H18	119.4
C7—C8—H8A	111.2	C17—C18—H18	119.4
C9—C8—H8A	111.2	C20—C19—C18	119.1 (3)
C7—C8—H8B	111.2	C20—C19—H19	120.4
C9—C8—H8B	111.2	C18—C19—H19	120.4
H8A—C8—H8B	109.1	C19—C20—C21	120.9 (2)
N2—C9—C10	114.15 (16)	C19—C20—H20	119.5
N2—C9—C8	101.42 (16)	C21—C20—H20	119.5
C10—C9—C8	112.58 (17)	C20—C21—C16	120.2 (2)
N2—C9—H9	109.5	C20—C21—H21	119.9
C10—C9—H9	109.5	C16—C21—H21	119.9
C8—C9—H9	109.5
C7—N1—N2—C16	164.09 (17)	C8—C9—C10—C15	−94.2 (2)
C7—N1—N2—C9	9.0 (2)	N2—C9—C10—C11	−161.80 (18)
C6—C1—C2—C3	−0.1 (4)	C8—C9—C10—C11	83.3 (2)
C1—C2—C3—C4	0.8 (4)	C15—C10—C11—C12	0.9 (3)
C2—C3—C4—C5	−1.1 (4)	C9—C10—C11—C12	−176.6 (2)
C3—C4—C5—C6	0.8 (3)	C10—C11—C12—C13	−0.7 (3)
C2—C1—C6—C5	−0.1 (3)	C11—C12—C13—C14	−0.1 (4)
C2—C1—C6—C7	178.0 (2)	C11—C12—C13—F1	179.6 (2)
C4—C5—C6—C1	−0.2 (3)	C12—C13—C14—C15	0.6 (3)
C4—C5—C6—C7	−178.33 (19)	F1—C13—C14—C15	−179.07 (19)
N2—N1—C7—C6	178.60 (17)	C11—C10—C15—C14	−0.4 (3)
N2—N1—C7—C8	−0.3 (2)	C9—C10—C15—C14	177.07 (19)
C1—C6—C7—N1	6.8 (3)	C13—C14—C15—C10	−0.4 (3)
C5—C6—C7—N1	−175.14 (19)	N1—N2—C16—C21	−164.84 (17)
C1—C6—C7—C8	−174.4 (2)	C9—N2—C16—C21	−13.1 (3)
C5—C6—C7—C8	3.6 (3)	N1—N2—C16—C17	17.6 (3)
N1—C7—C8—C9	−7.7 (2)	C9—N2—C16—C17	169.32 (18)
C6—C7—C8—C9	173.42 (18)	C21—C16—C17—C18	−0.1 (3)
N1—N2—C9—C10	−134.33 (17)	N2—C16—C17—C18	177.61 (18)
C16—N2—C9—C10	72.3 (2)	C16—C17—C18—C19	0.1 (3)
N1—N2—C9—C8	−13.0 (2)	C17—C18—C19—C20	−0.3 (4)
C16—N2—C9—C8	−166.37 (17)	C18—C19—C20—C21	0.6 (3)
C7—C8—C9—N2	11.62 (19)	C19—C20—C21—C16	−0.6 (3)
C7—C8—C9—C10	134.04 (18)	N2—C16—C21—C20	−177.35 (19)
N2—C9—C10—C15	20.8 (3)	C17—C16—C21—C20	0.3 (3)