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The pyrazoline ring in the title compound, C15H13BrN2O2, is approximately perpendicular to the furan ring, forming a dihedral angle of 88.0 (2)°. Weak inter­molecular C—H...O contacts help to stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702778X/tk2160sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680702778X/tk2160Isup2.hkl
Contains datablock I

CCDC reference: 654918

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.119
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.10 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.24 Ang.
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 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Pyrazoline and its derivatives are important and useful five-membered heterocyclic compounds which possess anti-viral (Rawal et al., 1963), anti-fungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. Further, 1-acetyl-3,5-diaryl-2-pyrazoline has been found to inhibit monoamine oxidases (Manna et al., 2002). As part of our on-going investgation of pyrazolines and their metal complexes, we report here the crystal structure of the title compound (I).

In the structure of (I) (Fig. 1), all bond lengths and angles fall in the normal range (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007). The dihedral angles formed by the pyrazolinyl ring with the phenyl and furan rings are 11.3 (2) and 88.0 (2)°, respectively. There are some intermolecular C—H···O contacts (Table 1) which stabilize the structure.

Related literature top

For related literature, see: Dhal et al. (1975); Fahrni et al. (2003); Guo et al. (2007); Kimura et al. (1977); Lombardino & Ottemes (1981); Manna et al. (2002); Rawal et al. (1963).

Experimental top

1-(p-Bromophenyl)-3-furan-2-propenyl-1-ketone (0.02 mol) and hydrazine (0.02 mol) were mixed and stirred in refluxing 99.5% acetic acid (40 ml) for 6 h. The mixture was poured into ice-water to afford colourless solids. The solids were filtered and washed with water until the pH of solution was about to 7.0.at room temperature. Single crystals of (I) suitable for the X-ray study were obtained by recrystallization from an ethanol solution of (I) held at room temperature; m. pt. 329.9 - 330.3 K.

Refinement top

H atoms were fixed geometrically and allowed to ride on their parent atoms with C—H distances = 0.93–0.96 Å, and with Uiso = 1.2–1.5Ueq of the parent atoms.

Structure description top

Pyrazoline and its derivatives are important and useful five-membered heterocyclic compounds which possess anti-viral (Rawal et al., 1963), anti-fungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. Further, 1-acetyl-3,5-diaryl-2-pyrazoline has been found to inhibit monoamine oxidases (Manna et al., 2002). As part of our on-going investgation of pyrazolines and their metal complexes, we report here the crystal structure of the title compound (I).

In the structure of (I) (Fig. 1), all bond lengths and angles fall in the normal range (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007). The dihedral angles formed by the pyrazolinyl ring with the phenyl and furan rings are 11.3 (2) and 88.0 (2)°, respectively. There are some intermolecular C—H···O contacts (Table 1) which stabilize the structure.

For related literature, see: Dhal et al. (1975); Fahrni et al. (2003); Guo et al. (2007); Kimura et al. (1977); Lombardino & Ottemes (1981); Manna et al. (2002); Rawal et al. (1963).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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 top
[Figure 1] Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level.
1-Acetyl-3-(4-bromophenyl)-5-(2-furyl)-2-pyrazoline top
Crystal data top
C15H13BrN2O2F(000) = 672
Mr = 333.18Dx = 1.587 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2387 reflections
a = 8.1417 (17) Åθ = 2.3–25.3°
b = 26.757 (6) ŵ = 2.95 mm1
c = 7.0974 (15) ÅT = 298 K
β = 115.587 (2)°Plan, colourless
V = 1394.5 (5) Å30.49 × 0.36 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2461 independent reflections
Radiation source: fine-focus sealed tube1948 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 99
Tmin = 0.326, Tmax = 0.757k = 2131
5796 measured reflectionsl = 87
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0511P)2 + 0.5202P]
where P = (Fo2 + 2Fc2)/3
2461 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C15H13BrN2O2V = 1394.5 (5) Å3
Mr = 333.18Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.1417 (17) ŵ = 2.95 mm1
b = 26.757 (6) ÅT = 298 K
c = 7.0974 (15) Å0.49 × 0.36 × 0.10 mm
β = 115.587 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2461 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
1948 reflections with I > 2σ(I)
Tmin = 0.326, Tmax = 0.757Rint = 0.044
5796 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.05Δρmax = 0.70 e Å3
2461 reflectionsΔρmin = 0.43 e Å3
182 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
xyzUiso*/Ueq
C10.0947 (5)0.41162 (13)0.4859 (5)0.0419 (8)
H10.02570.38320.42790.050*
C20.1101 (5)0.44764 (14)0.3554 (6)0.0456 (9)
H20.05270.44360.21120.055*
C30.2128 (5)0.48981 (13)0.4436 (5)0.0385 (8)
C40.2965 (5)0.49611 (14)0.6560 (6)0.0486 (9)
H40.36450.52480.71290.058*
C50.2800 (5)0.45990 (14)0.7856 (6)0.0455 (9)
H50.33610.46430.92970.055*
C60.1790 (4)0.41671 (13)0.7003 (5)0.0336 (7)
C70.1609 (4)0.37748 (12)0.8347 (5)0.0331 (7)
C80.0343 (5)0.33378 (13)0.7547 (5)0.0398 (8)
H8A0.07350.31120.67520.048*
H8B0.08910.34470.66750.048*
C90.0472 (4)0.30873 (13)0.9553 (5)0.0373 (8)
H90.07920.27340.95530.045*
C100.1191 (4)0.31280 (12)0.9911 (5)0.0355 (8)
C110.2383 (5)0.27922 (15)0.9944 (6)0.0470 (9)
H110.23150.24480.98130.056*
C120.3780 (5)0.30560 (16)1.0217 (6)0.0535 (10)
H120.47960.29201.03060.064*
C130.3341 (5)0.35353 (17)1.0319 (6)0.0521 (10)
H130.40200.37941.05010.063*
C140.3013 (5)0.32032 (15)1.3154 (6)0.0440 (9)
C150.4664 (5)0.34952 (16)1.4508 (6)0.0531 (10)
H15A0.52740.33321.58350.080*
H15B0.43090.38251.47120.080*
H15C0.54720.35171.38470.080*
N10.2571 (4)0.37738 (10)1.0338 (4)0.0350 (7)
N20.2051 (4)0.33615 (10)1.1156 (4)0.0367 (7)
O10.1747 (3)0.35984 (9)1.0122 (4)0.0475 (6)
O20.2510 (4)0.28316 (11)1.3765 (5)0.0643 (8)
Br10.23278 (6)0.540128 (15)0.26614 (7)0.0570 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.041 (2)0.042 (2)0.040 (2)0.0056 (16)0.0150 (17)0.0054 (15)
C20.049 (2)0.055 (2)0.033 (2)0.0008 (18)0.0177 (18)0.0001 (16)
C30.0306 (18)0.044 (2)0.045 (2)0.0050 (15)0.0202 (17)0.0076 (15)
C40.045 (2)0.046 (2)0.050 (2)0.0078 (18)0.0164 (19)0.0002 (17)
C50.045 (2)0.049 (2)0.036 (2)0.0021 (17)0.0113 (18)0.0000 (16)
C60.0237 (16)0.0426 (19)0.0336 (18)0.0033 (14)0.0115 (14)0.0002 (14)
C70.0257 (17)0.0385 (19)0.036 (2)0.0038 (14)0.0138 (15)0.0005 (14)
C80.038 (2)0.042 (2)0.041 (2)0.0011 (16)0.0185 (17)0.0042 (15)
C90.0318 (19)0.0380 (19)0.042 (2)0.0008 (15)0.0159 (16)0.0005 (15)
C100.0321 (18)0.0379 (19)0.0329 (18)0.0024 (15)0.0105 (15)0.0013 (14)
C110.038 (2)0.042 (2)0.061 (3)0.0017 (17)0.0208 (19)0.0065 (17)
C120.035 (2)0.069 (3)0.059 (3)0.000 (2)0.0223 (19)0.013 (2)
C130.038 (2)0.072 (3)0.053 (2)0.013 (2)0.0256 (19)0.0008 (19)
C140.0339 (19)0.057 (2)0.042 (2)0.0057 (17)0.0179 (17)0.0104 (17)
C150.035 (2)0.076 (3)0.040 (2)0.0051 (19)0.0084 (18)0.0077 (19)
N10.0277 (15)0.0415 (17)0.0363 (17)0.0012 (12)0.0142 (13)0.0030 (12)
N20.0264 (14)0.0425 (17)0.0372 (17)0.0024 (13)0.0098 (13)0.0052 (13)
O10.0433 (15)0.0425 (15)0.0624 (17)0.0000 (12)0.0282 (13)0.0055 (12)
O20.0591 (19)0.072 (2)0.0582 (18)0.0086 (15)0.0221 (15)0.0243 (15)
Br10.0593 (3)0.0572 (3)0.0622 (3)0.0015 (2)0.0335 (2)0.01656 (19)
Geometric parameters (Å, º) top
C1—C21.379 (5)C9—N21.490 (4)
C1—C61.380 (5)C9—H90.9800
C1—H10.9300C10—C111.330 (5)
C2—C31.383 (5)C10—O11.367 (4)
C2—H20.9300C11—C121.421 (5)
C3—C41.370 (5)C11—H110.9300
C3—Br11.898 (3)C12—C131.325 (6)
C4—C51.382 (5)C12—H120.9300
C4—H40.9300C13—O11.375 (4)
C5—C61.396 (5)C13—H130.9300
C5—H50.9300C14—O21.224 (4)
C6—C71.467 (5)C14—N21.358 (5)
C7—N11.287 (4)C14—C151.492 (5)
C7—C81.499 (5)C15—H15A0.9600
C8—C91.535 (5)C15—H15B0.9600
C8—H8A0.9700C15—H15C0.9600
C8—H8B0.9700N1—N21.395 (4)
C9—C101.486 (5)
C2—C1—C6121.7 (3)C10—C9—H9109.4
C2—C1—H1119.1N2—C9—H9109.4
C6—C1—H1119.1C8—C9—H9109.4
C1—C2—C3118.6 (3)C11—C10—O1110.0 (3)
C1—C2—H2120.7C11—C10—C9132.8 (3)
C3—C2—H2120.7O1—C10—C9117.1 (3)
C4—C3—C2121.0 (3)C10—C11—C12107.4 (4)
C4—C3—Br1119.9 (3)C10—C11—H11126.3
C2—C3—Br1119.1 (3)C12—C11—H11126.3
C3—C4—C5120.0 (3)C13—C12—C11106.0 (3)
C3—C4—H4120.0C13—C12—H12127.0
C5—C4—H4120.0C11—C12—H12127.0
C4—C5—C6120.0 (3)C12—C13—O1111.0 (3)
C4—C5—H5120.0C12—C13—H13124.5
C6—C5—H5120.0O1—C13—H13124.5
C1—C6—C5118.6 (3)O2—C14—N2119.5 (4)
C1—C6—C7120.3 (3)O2—C14—C15122.9 (4)
C5—C6—C7121.1 (3)N2—C14—C15117.5 (3)
N1—C7—C6122.1 (3)C14—C15—H15A109.5
N1—C7—C8114.0 (3)C14—C15—H15B109.5
C6—C7—C8123.9 (3)H15A—C15—H15B109.5
C7—C8—C9103.3 (3)C14—C15—H15C109.5
C7—C8—H8A111.1H15A—C15—H15C109.5
C9—C8—H8A111.1H15B—C15—H15C109.5
C7—C8—H8B111.1C7—N1—N2108.0 (3)
C9—C8—H8B111.1C14—N2—N1122.6 (3)
H8A—C8—H8B109.1C14—N2—C9124.2 (3)
C10—C9—N2112.5 (3)N1—N2—C9112.9 (3)
C10—C9—C8115.1 (3)C10—O1—C13105.6 (3)
N2—C9—C8100.6 (3)
C6—C1—C2—C30.1 (6)C8—C9—C10—O161.3 (4)
C1—C2—C3—C40.6 (6)O1—C10—C11—C120.8 (4)
C1—C2—C3—Br1179.2 (3)C9—C10—C11—C12175.8 (4)
C2—C3—C4—C50.4 (6)C10—C11—C12—C130.3 (4)
Br1—C3—C4—C5179.0 (3)C11—C12—C13—O10.2 (5)
C3—C4—C5—C60.4 (6)C6—C7—N1—N2178.7 (3)
C2—C1—C6—C50.9 (5)C8—C7—N1—N22.5 (4)
C2—C1—C6—C7179.5 (3)O2—C14—N2—N1178.3 (3)
C4—C5—C6—C11.1 (5)C15—C14—N2—N11.4 (5)
C4—C5—C6—C7179.4 (3)O2—C14—N2—C95.3 (5)
C1—C6—C7—N1170.1 (3)C15—C14—N2—C9174.3 (3)
C5—C6—C7—N110.4 (5)C7—N1—N2—C14168.2 (3)
C1—C6—C7—C88.5 (5)C7—N1—N2—C95.5 (4)
C5—C6—C7—C8171.0 (3)C10—C9—N2—C1473.8 (4)
N1—C7—C8—C98.9 (4)C8—C9—N2—C14163.2 (3)
C6—C7—C8—C9172.4 (3)C10—C9—N2—N1112.6 (3)
C7—C8—C9—C10110.6 (3)C8—C9—N2—N110.4 (3)
C7—C8—C9—N210.6 (3)C11—C10—O1—C130.9 (4)
N2—C9—C10—C11132.1 (4)C9—C10—O1—C13176.8 (3)
C8—C9—C10—C11113.5 (4)C12—C13—O1—C100.7 (4)
N2—C9—C10—O153.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O2i0.982.293.148 (4)146
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC15H13BrN2O2
Mr333.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)8.1417 (17), 26.757 (6), 7.0974 (15)
β (°) 115.587 (2)
V3)1394.5 (5)
Z4
Radiation typeMo Kα
µ (mm1)2.95
Crystal size (mm)0.49 × 0.36 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.326, 0.757
No. of measured, independent and
observed [I > 2σ(I)] reflections
5796, 2461, 1948
Rint0.044
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.119, 1.05
No. of reflections2461
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.70, 0.43

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O2i0.982.293.148 (4)146
Symmetry code: (i) x, y+1/2, z1/2.
 

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