organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

5-(2-Fur­yl)-3-methyl-1-(3-nitro­phen­yl)-4,5-di­hydro-1H-pyrazole

aEnergy Research Institute Co Ltd, Henan Academy of Sciences, Zhengzhou 450000, People's Republic of China, and bSchool of Chemistry and Biological Engineering, Guilin University of Technology, People's Republic of China
*Correspondence e-mail: junqiangchen2009@126.com

(Received 6 August 2009; accepted 10 August 2009; online 15 August 2009)

In the title compound, C14H13N3O3, the pyrazoline ring assumes an envelope conformation with the furanyl-bearing C atom at the flap position. The dihedral angle between the furan and nitrobenzene rings is 84.40 (9)°. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of pyrazoline derivatives, see: Hatheway et al. (1978[Hatheway, G. J., Hansch, C., Kim, K. H., Milstein, S. R., Schmidt, C. L., Smith, R. N. & Quinn, F. R. (1978). J. Med. Chem. 21, 563-567.]); Mahajan et al. (1991[Mahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245-246.]); Sobczak & Pawlaczyk (1998[Sobczak, H. & Pawlaczyk, J. (1998). Acta Pol. Pharm. 55, 279-283.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13N3O3

  • Mr = 271.27

  • Triclinic, [P \overline 1]

  • a = 6.2089 (2) Å

  • b = 7.8581 (3) Å

  • c = 14.3800 (4) Å

  • α = 105.764 (2)°

  • β = 97.054 (2)°

  • γ = 96.944 (2)°

  • V = 661.31 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.31 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: none

  • 9707 measured reflections

  • 2590 independent reflections

  • 1778 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.121

  • S = 1.10

  • 2590 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12A⋯O1i 0.93 2.51 3.311 (2) 144
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

The derivatives of pyrazoline are mostly used in medicine, for example as antitumor (Hatheway et al., 1978), analgesic (Sobczak & Pawlaczyk, 1998), and antimicrobial (Mahajan et al., 1991) agents. As part of our work, the new title compound (I) are synthesized in our group.

The pyrazoline ring assumes an envelope conformation with the furanyl-bearing carbon atom at the flap position (Fig. 1). Intermolecular weak C—H···O hydrogen bonding is present in the crystal structure. (Fig. 2 and Table 1).

Related literature top

For applications of pyrazoline derivatives, see: Hatheway et al. (1978); Mahajan et al. (1991); Sobczak & Pawlaczyk (1998).

Experimental top

3-Nitrophenylhydrazine (1 mmol, 0.153 g) was dissolved in anhydrous ethanol (15 ml). The mixture was stirred for several min at 351 K, furylideneacetone (1 mmol, 0.136 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol, bronze single crystals of (I) were obtained after 3 d.

Refinement top

All H atoms were positioned geometrically and refined as riding with C—H = 0.93 (aromatic), 0.97 (methylene), 0.98 (methine) and 0.96 Å (methyl), with Uiso(H)=1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing of (I), showing the intermolecular hydrogen bonds as dashed lines.
5-(2-Furyl)-3-methyl-1-(3-nitrophenyl)-4,5-dihydro-1H-pyrazole top
Crystal data top
C14H13N3O3Z = 2
Mr = 271.27F(000) = 284
Triclinic, P1Dx = 1.362 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2089 (2) ÅCell parameters from 1598 reflections
b = 7.8581 (3) Åθ = 3.5–24.6°
c = 14.3800 (4) ŵ = 0.10 mm1
α = 105.764 (2)°T = 296 K
β = 97.054 (2)°Block, bronze
γ = 96.944 (2)°0.31 × 0.15 × 0.10 mm
V = 661.31 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1778 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 26.0°, θmin = 3.5°
ω scansh = 77
9707 measured reflectionsk = 89
2590 independent reflectionsl = 1717
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0608P)2]
where P = (Fo2 + 2Fc2)/3
2590 reflections(Δ/σ)max = 0.003
181 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C14H13N3O3γ = 96.944 (2)°
Mr = 271.27V = 661.31 (4) Å3
Triclinic, P1Z = 2
a = 6.2089 (2) ÅMo Kα radiation
b = 7.8581 (3) ŵ = 0.10 mm1
c = 14.3800 (4) ÅT = 296 K
α = 105.764 (2)°0.31 × 0.15 × 0.10 mm
β = 97.054 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1778 reflections with I > 2σ(I)
9707 measured reflectionsRint = 0.036
2590 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.10Δρmax = 0.14 e Å3
2590 reflectionsΔρmin = 0.21 e Å3
181 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
O0.36743 (18)0.34679 (15)0.90208 (8)0.0586 (3)
N10.1661 (2)0.62239 (17)0.78604 (10)0.0496 (4)
N20.2000 (2)0.45740 (16)0.72794 (10)0.0491 (4)
C90.3755 (2)0.4521 (2)0.67745 (11)0.0429 (4)
C140.5059 (2)0.6102 (2)0.67820 (11)0.0460 (4)
H14A0.47720.72110.71320.055*
C70.0168 (3)0.5942 (2)0.83623 (13)0.0534 (4)
C100.4224 (3)0.2892 (2)0.62195 (12)0.0546 (4)
H10A0.33470.18260.61910.066*
C40.2531 (2)0.2318 (2)0.81601 (12)0.0477 (4)
C130.6784 (2)0.5987 (2)0.62600 (12)0.0514 (4)
N30.8105 (2)0.7665 (2)0.62761 (12)0.0680 (5)
O10.9707 (2)0.7615 (2)0.58611 (11)0.0934 (5)
C50.0941 (2)0.3072 (2)0.75855 (12)0.0508 (4)
H5A0.01380.21260.70100.061*
C120.7298 (3)0.4395 (3)0.57272 (12)0.0611 (5)
H12A0.84870.43650.53910.073*
C60.0684 (3)0.4007 (3)0.81836 (14)0.0615 (5)
H6A0.21660.36860.78170.074*
H6B0.06770.37060.87950.074*
C10.4967 (3)0.2476 (3)0.94299 (14)0.0607 (5)
H1B0.59240.29201.00220.073*
O20.7571 (3)0.9062 (2)0.67000 (14)0.1046 (6)
C110.5976 (3)0.2848 (3)0.57136 (13)0.0642 (5)
H11A0.62700.17480.53550.077*
C30.3090 (3)0.0707 (2)0.80439 (14)0.0660 (5)
H3A0.25500.03080.75180.079*
C20.4665 (3)0.0818 (3)0.88708 (14)0.0673 (5)
H2A0.53500.01080.89920.081*
C80.0654 (3)0.7433 (3)0.90245 (15)0.0793 (6)
H8A0.01410.85560.90190.119*
H8B0.04440.73290.96780.119*
H8C0.21910.73810.88060.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O0.0577 (7)0.0535 (7)0.0622 (8)0.0133 (5)0.0000 (6)0.0156 (6)
N10.0513 (8)0.0481 (8)0.0555 (8)0.0152 (6)0.0159 (6)0.0190 (7)
N20.0507 (7)0.0414 (7)0.0613 (9)0.0090 (6)0.0178 (6)0.0206 (7)
C90.0443 (8)0.0457 (9)0.0417 (9)0.0103 (7)0.0050 (7)0.0172 (7)
C140.0459 (8)0.0467 (9)0.0464 (9)0.0077 (7)0.0087 (7)0.0147 (7)
C70.0454 (8)0.0673 (11)0.0568 (10)0.0186 (8)0.0109 (8)0.0284 (9)
C100.0639 (10)0.0459 (10)0.0528 (10)0.0079 (8)0.0105 (8)0.0125 (8)
C40.0474 (8)0.0414 (9)0.0544 (10)0.0009 (7)0.0061 (7)0.0179 (8)
C130.0452 (9)0.0591 (10)0.0501 (10)0.0017 (8)0.0074 (7)0.0191 (8)
N30.0584 (9)0.0749 (12)0.0685 (10)0.0040 (8)0.0163 (8)0.0210 (9)
O10.0729 (9)0.1114 (12)0.0966 (11)0.0083 (8)0.0418 (8)0.0290 (9)
C50.0440 (8)0.0488 (9)0.0621 (10)0.0003 (7)0.0046 (7)0.0256 (8)
C120.0591 (10)0.0759 (13)0.0516 (11)0.0182 (9)0.0200 (8)0.0159 (9)
C60.0403 (8)0.0813 (13)0.0765 (12)0.0102 (8)0.0121 (8)0.0440 (11)
C10.0531 (10)0.0751 (13)0.0613 (11)0.0207 (9)0.0076 (8)0.0285 (10)
O20.0990 (12)0.0602 (9)0.1522 (16)0.0069 (8)0.0581 (11)0.0187 (10)
C110.0777 (12)0.0602 (11)0.0550 (11)0.0230 (10)0.0176 (10)0.0093 (9)
C30.0813 (13)0.0457 (10)0.0690 (13)0.0129 (9)0.0027 (10)0.0164 (9)
C20.0761 (12)0.0621 (13)0.0761 (13)0.0288 (10)0.0118 (10)0.0333 (11)
C80.0778 (13)0.0996 (16)0.0771 (14)0.0422 (12)0.0352 (11)0.0316 (12)
Geometric parameters (Å, º) top
O—C41.3689 (18)N3—O21.208 (2)
O—C11.372 (2)N3—O11.2209 (19)
N1—C71.277 (2)C5—C61.532 (2)
N1—N21.3940 (18)C5—H5A0.9800
N2—C91.3803 (19)C12—C111.376 (3)
N2—C51.4784 (19)C12—H12A0.9300
C9—C141.396 (2)C6—H6A0.9700
C9—C101.397 (2)C6—H6B0.9700
C14—C131.379 (2)C1—C21.309 (2)
C14—H14A0.9300C1—H1B0.9300
C7—C81.482 (2)C11—H11A0.9300
C7—C61.489 (3)C3—C21.420 (2)
C10—C111.380 (2)C3—H3A0.9300
C10—H10A0.9300C2—H2A0.9300
C4—C31.325 (2)C8—H8A0.9600
C4—C51.488 (2)C8—H8B0.9600
C13—C121.375 (2)C8—H8C0.9600
C13—N31.459 (2)
C4—O—C1105.97 (13)C4—C5—H5A110.0
C7—N1—N2108.34 (13)C6—C5—H5A110.0
C9—N2—N1118.80 (12)C13—C12—C11117.03 (16)
C9—N2—C5125.31 (13)C13—C12—H12A121.5
N1—N2—C5111.64 (12)C11—C12—H12A121.5
N2—C9—C14120.55 (14)C7—C6—C5103.00 (13)
N2—C9—C10120.96 (14)C7—C6—H6A111.2
C14—C9—C10118.47 (14)C5—C6—H6A111.2
C13—C14—C9118.59 (15)C7—C6—H6B111.2
C13—C14—H14A120.7C5—C6—H6B111.2
C9—C14—H14A120.7H6A—C6—H6B109.1
N1—C7—C8121.87 (16)C2—C1—O110.60 (15)
N1—C7—C6113.46 (15)C2—C1—H1B124.7
C8—C7—C6124.64 (16)O—C1—H1B124.7
C11—C10—C9120.67 (16)C12—C11—C10121.50 (17)
C11—C10—H10A119.7C12—C11—H11A119.3
C9—C10—H10A119.7C10—C11—H11A119.3
C3—C4—O109.50 (15)C4—C3—C2107.27 (16)
C3—C4—C5134.10 (17)C4—C3—H3A126.4
O—C4—C5116.37 (14)C2—C3—H3A126.4
C12—C13—C14123.72 (16)C1—C2—C3106.65 (16)
C12—C13—N3119.04 (15)C1—C2—H2A126.7
C14—C13—N3117.24 (15)C3—C2—H2A126.7
O2—N3—O1122.13 (17)C7—C8—H8A109.5
O2—N3—C13118.76 (15)C7—C8—H8B109.5
O1—N3—C13119.11 (17)H8A—C8—H8B109.5
N2—C5—C4112.93 (12)C7—C8—H8C109.5
N2—C5—C6100.18 (13)H8A—C8—H8C109.5
C4—C5—C6113.50 (14)H8B—C8—H8C109.5
N2—C5—H5A110.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O1i0.932.513.311 (2)144
Symmetry code: (i) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC14H13N3O3
Mr271.27
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)6.2089 (2), 7.8581 (3), 14.3800 (4)
α, β, γ (°)105.764 (2), 97.054 (2), 96.944 (2)
V3)661.31 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.31 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9707, 2590, 1778
Rint0.036
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.121, 1.10
No. of reflections2590
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O1i0.932.513.311 (2)144
Symmetry code: (i) x+2, y+1, z+1.
 

References

First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationHatheway, G. J., Hansch, C., Kim, K. H., Milstein, S. R., Schmidt, C. L., Smith, R. N. & Quinn, F. R. (1978). J. Med. Chem. 21, 563–567.  CrossRef CAS PubMed Web of Science Google Scholar
First citationMahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245–246.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSobczak, H. & Pawlaczyk, J. (1998). Acta Pol. Pharm. 55, 279–283.  CAS PubMed Google Scholar

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ISSN: 2056-9890
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