1-{3-(4-Methyl­phen­yl)-5-[5-(2-nitro­phen­yl)furan-2-yl]-4,5-di­hydro-1H-pyrazol-1-yl}ethanone

Vinutha, N.; Madan Kumar, S.; Vidyashree Jois, B.S.; Balakrishna, K.; Lokanath, N.K.; Revannasiddaiah, D.

doi:10.1107/S1600536813024690

organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1528

doi:10.1107/S1600536813024690

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1-{3-(4-Methylphenyl)-5-[5-(2-nitrophenyl)furan-2-yl]-4,5-dihydro-1H-pyrazol-1-yl}ethanone

N. Vinutha,^a S. Madan Kumar,^a B. S. Vidyashree Jois,^b Kalluraya Balakrishna,^b N. K. Lokanath ^a and D. Revannasiddaiah ^a ^*

^aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: dr@physics.uni-mysore.ac.in

(Received 2 September 2013; accepted 4 September 2013; online 12 September 2013)

In the title compound, C₂₂H₁₉N₃O₄, the dihedral angle between the furan and pyrazole rings is 82.73 (19)° while the dihedral angles between the furan and pyrazole rings and their attached benzene rings are 31.93 (18) and 1.88 (18)°, respectively. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R₂²(16) loops. In addition, weak C—H⋯π and aromatic π–π stacking [minimum centroid–centroid distance = 3.5374 (17) Å] interactions are observed.

Related literature

For background to the biological properties of pyrazole derivatives, see: Amir et al. (2008 ); Husain et al. (2008 ).

Experimental

Crystal data

C₂₂H₁₉N₃O₄
M_r = 389.40
Triclinic, $[P \overline 1]$
a = 7.6235 (3) Å
b = 10.5652 (4) Å
c = 13.1177 (4) Å
α = 103.344 (2)°
β = 95.025 (2)°
γ = 108.221 (2)°
V = 961.78 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.78 mm⁻¹
T = 296 K
0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.842, T_max = 0.854
10640 measured reflections
3083 independent reflections
2186 reflections with I > 2σ(I)
R_int = 0.138

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.242
S = 1.06
3083 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C23–C28 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O19ⁱ	0.93	2.56	3.462 (4)	162
C18—H18C⋯Cg4ⁱⁱ	0.96	2.69	3.595 (4)	158
Symmetry codes: (i) -x, -y, -z+2; (ii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813024690/hb7133sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813024690/hb7133Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813024690/hb7133Isup3.cml

checkCIF report

Comment top

The ongoing work in our lab for synthesizing pyrozoline derivatives resulted the title molecule. Similar compounds are used for the preparation of drugs in the pharmacological industries (Amir et al., 2008; Husain et al., 2008).

In the title compound (Fig. 1), the pyrazole ring makes a dihedral angle of 82.73 (19) °, 88.84 (18) ° and 1.88 (18) ° with furan, nitrophenyl and terminal methylphenyl rings, respectively. The furan ring makes a dihedral angle of 82.35 (18) ° and 31.93 (18) ° with methyl phenyl and nitrophenyl rings, respectively. The dihedral angle between terminal nitrophenyl and methylphenyl ring is 88.23 (17) °.

The title molecules are linked to one another with C14—H14···O19 intermolecular hydrogen bonds with R₂²(16) ring motif (Fig. 2 and Table 1). In addition, short contacts C—H···π (Cg4) with distance 3.595 (4) Å (angle 158 °) [-x, -y, z - 1]. And π···π between Cg2 and Cg1 with distance 3.5374 (17) ° [x,y,z] and between Cg2 and Cg4 with a distance 3.641 (2) ° [x - 1, -y, z - 1] were observed, where Cg1:O11/C10/C14/C13/C12, Cg2:N16/N20/C21/C22/C15 and Cg4:C23/C24/C25/C26/C27/C28.

Related literature top

For background to the biological properties of pyrazole derivatives, see: Amir et al. (2008); Husain et al. (2008).

Experimental top

A mixture of 4-methylphenyl-3-[5-(2-nitrophenyl)furan-2-yl]prop-2-en-1-one (10 mmol), hydrazine hydrate (50 mmol) and glacial acetic acid (40 ml) were refluxed for 24 h. The resulting mixture was poured into water (100 ml) and allowed to stand. The precipitate that formed was separated by filtration, washed with cold water and then recrystallized from mixed DMF-ethanol solvents to yield brown blocks.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELX:97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP diagram of the title compound with 50% probability ellipsoids.
	Fig. 2. Packing diagram of molecule, viewed along the crystallographic a axis. Dotted lines represent hydrogen bonds.

1-{3-(4-Methylphenyl)-5-[5-(2-nitrophenyl)furan-2-yl]-4,5-dihydro-1H-pyrazol-1-yl}ethanone top

Crystal data top

C₂₂H₁₉N₃O₄	Z = 2
M_r = 389.40	F(000) = 408
Triclinic, P1	D_x = 1.345 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.6235 (3) Å	Cell parameters from 3083 reflections
b = 10.5652 (4) Å	θ = 3.5–64.8°
c = 13.1177 (4) Å	µ = 0.78 mm⁻¹
α = 103.344 (2)°	T = 296 K
β = 95.025 (2)°	Block, brown
γ = 108.221 (2)°	0.23 × 0.22 × 0.21 mm
V = 961.78 (6) Å³

Data collection top

Bruker X8 Proteum CCD diffractometer	3083 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2186 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.138
Detector resolution: 10.7 pixels mm^-1	θ_max = 64.8°, θ_min = 3.5°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→12
T_min = 0.842, T_max = 0.854	l = −14→15
10640 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.084	H-atom parameters constrained
wR(F²) = 0.242	w = 1/[σ²(F_o²) + (0.1607P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3083 reflections	Δρ_max = 0.40 e Å⁻³
265 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (3)

Crystal data top

C₂₂H₁₉N₃O₄	γ = 108.221 (2)°
M_r = 389.40	V = 961.78 (6) Å³
Triclinic, P1	Z = 2
a = 7.6235 (3) Å	Cu Kα radiation
b = 10.5652 (4) Å	µ = 0.78 mm⁻¹
c = 13.1177 (4) Å	T = 296 K
α = 103.344 (2)°	0.23 × 0.22 × 0.21 mm
β = 95.025 (2)°

Data collection top

Bruker X8 Proteum CCD diffractometer	3083 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2186 reflections with I > 2σ(I)
T_min = 0.842, T_max = 0.854	R_int = 0.138
10640 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	0 restraints
wR(F²) = 0.242	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
3083 reflections	Δρ_min = −0.38 e Å⁻³
265 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O8	0.2462 (4)	0.4170 (3)	0.8072 (2)	0.0736 (10)
O9	0.0362 (6)	0.3831 (5)	0.6738 (2)	0.1186 (18)
O11	0.1066 (3)	0.1532 (2)	0.82063 (14)	0.0429 (7)
O19	0.0746 (4)	−0.2396 (2)	0.77708 (19)	0.0647 (9)
N7	0.0831 (5)	0.3916 (3)	0.7666 (2)	0.0603 (11)
N16	0.1731 (4)	−0.0929 (2)	0.67816 (18)	0.0445 (8)
N20	0.1833 (4)	−0.0661 (2)	0.57957 (19)	0.0423 (8)
C1	−0.2096 (5)	0.2889 (3)	0.9665 (3)	0.0561 (11)
C2	−0.3242 (5)	0.3645 (4)	0.9620 (3)	0.0652 (14)
C3	−0.3090 (5)	0.4456 (4)	0.8924 (3)	0.0649 (14)
C4	−0.1778 (5)	0.4506 (3)	0.8273 (3)	0.0587 (11)
C5	−0.0621 (4)	0.3744 (3)	0.8330 (2)	0.0469 (10)
C6	−0.0729 (4)	0.2910 (3)	0.9021 (2)	0.0418 (9)
C10	0.0452 (4)	0.2079 (3)	0.9105 (2)	0.0425 (9)
C12	0.2155 (4)	0.0806 (3)	0.8501 (2)	0.0415 (9)
C13	0.2212 (5)	0.0893 (3)	0.9544 (2)	0.0497 (11)
C14	0.1110 (5)	0.1697 (3)	0.9934 (2)	0.0505 (11)
C15	0.3075 (4)	0.0204 (3)	0.7665 (2)	0.0447 (10)
C17	0.0708 (5)	−0.2192 (3)	0.6880 (2)	0.0472 (11)
C18	−0.0432 (5)	−0.3260 (3)	0.5893 (3)	0.0592 (11)
C21	0.3124 (4)	0.0530 (3)	0.5932 (2)	0.0414 (9)
C22	0.4090 (4)	0.1216 (3)	0.7063 (2)	0.0502 (10)
C23	0.3564 (4)	0.1109 (3)	0.5040 (2)	0.0440 (10)
C24	0.2619 (4)	0.0440 (3)	0.4011 (3)	0.0487 (10)
C25	0.3054 (5)	0.1030 (3)	0.3190 (3)	0.0539 (12)
C26	0.4428 (5)	0.2314 (4)	0.3360 (3)	0.0556 (12)
C27	0.5380 (5)	0.2980 (4)	0.4389 (3)	0.0628 (12)
C28	0.4980 (5)	0.2405 (3)	0.5222 (3)	0.0565 (11)
C29	0.4863 (6)	0.2965 (5)	0.2462 (4)	0.0812 (17)
H1	−0.22270	0.23450	1.01380	0.0670*
H2	−0.41350	0.36140	1.00620	0.0780*
H3	−0.38780	0.49690	0.88980	0.0780*
H4	−0.16700	0.50470	0.77980	0.0700*
H13	0.28560	0.04970	0.99370	0.0600*
H14	0.08830	0.19190	1.06270	0.0610*
H15	0.39680	−0.01490	0.79860	0.0540*
H18A	−0.08350	−0.41510	0.60300	0.0890*
H18B	0.03140	−0.32780	0.53400	0.0890*
H18C	−0.15080	−0.30380	0.56720	0.0890*
H22A	0.39530	0.21130	0.73180	0.0600*
H22B	0.54140	0.13360	0.71370	0.0600*
H24	0.16790	−0.04200	0.38710	0.0580*
H25	0.24060	0.05540	0.25040	0.0650*
H27	0.63170	0.38400	0.45230	0.0750*
H28	0.56480	0.28760	0.59050	0.0680*
H29A	0.37170	0.28030	0.20040	0.1220*
H29B	0.56460	0.25620	0.20630	0.1220*
H29C	0.55040	0.39440	0.27470	0.1220*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O8	0.0562 (17)	0.0598 (16)	0.093 (2)	0.0000 (13)	0.0194 (14)	0.0235 (14)
O9	0.146 (3)	0.173 (4)	0.052 (2)	0.063 (3)	0.025 (2)	0.045 (2)
O11	0.0469 (13)	0.0401 (11)	0.0322 (11)	0.0069 (9)	0.0038 (9)	0.0041 (9)
O19	0.0872 (19)	0.0492 (14)	0.0484 (15)	0.0091 (12)	0.0117 (12)	0.0156 (11)
N7	0.074 (2)	0.0525 (17)	0.0494 (18)	0.0117 (15)	0.0152 (15)	0.0165 (13)
N16	0.0507 (16)	0.0337 (13)	0.0352 (14)	0.0011 (11)	0.0061 (11)	0.0024 (10)
N20	0.0471 (15)	0.0354 (13)	0.0372 (14)	0.0060 (11)	0.0074 (11)	0.0073 (10)
C1	0.053 (2)	0.0454 (18)	0.058 (2)	0.0071 (16)	0.0147 (16)	0.0032 (15)
C2	0.046 (2)	0.055 (2)	0.076 (3)	0.0071 (17)	0.0142 (17)	−0.0045 (18)
C3	0.049 (2)	0.052 (2)	0.077 (3)	0.0146 (17)	−0.0064 (19)	−0.0037 (18)
C4	0.054 (2)	0.0459 (19)	0.062 (2)	0.0099 (16)	−0.0063 (17)	0.0042 (16)
C5	0.0431 (18)	0.0403 (16)	0.0397 (17)	0.0005 (14)	−0.0028 (13)	0.0006 (13)
C6	0.0390 (17)	0.0326 (15)	0.0387 (16)	0.0003 (12)	0.0022 (12)	−0.0003 (12)
C10	0.0443 (17)	0.0364 (15)	0.0343 (16)	0.0024 (13)	0.0076 (12)	0.0017 (12)
C12	0.0425 (17)	0.0342 (15)	0.0372 (16)	0.0050 (13)	−0.0002 (12)	0.0034 (12)
C13	0.061 (2)	0.0467 (18)	0.0371 (18)	0.0125 (16)	0.0043 (14)	0.0129 (14)
C14	0.065 (2)	0.0474 (18)	0.0332 (17)	0.0101 (16)	0.0105 (14)	0.0116 (13)
C15	0.0438 (18)	0.0418 (16)	0.0360 (17)	0.0050 (13)	−0.0009 (13)	0.0035 (13)
C17	0.056 (2)	0.0347 (16)	0.0447 (19)	0.0083 (14)	0.0122 (14)	0.0079 (13)
C18	0.067 (2)	0.0382 (17)	0.052 (2)	−0.0020 (16)	0.0078 (17)	0.0026 (15)
C21	0.0368 (16)	0.0359 (15)	0.0432 (17)	0.0043 (12)	0.0065 (12)	0.0066 (12)
C22	0.0432 (18)	0.0457 (17)	0.0453 (19)	−0.0002 (14)	0.0049 (13)	0.0037 (14)
C23	0.0371 (17)	0.0373 (15)	0.0501 (19)	0.0035 (13)	0.0059 (13)	0.0111 (13)
C24	0.0404 (17)	0.0403 (16)	0.052 (2)	0.0003 (13)	0.0050 (14)	0.0070 (14)
C25	0.050 (2)	0.054 (2)	0.048 (2)	0.0048 (16)	0.0060 (15)	0.0147 (15)
C26	0.045 (2)	0.057 (2)	0.064 (2)	0.0092 (16)	0.0070 (15)	0.0276 (17)
C27	0.048 (2)	0.052 (2)	0.072 (2)	−0.0072 (16)	0.0014 (17)	0.0230 (18)
C28	0.0463 (19)	0.0471 (18)	0.056 (2)	−0.0073 (15)	−0.0026 (15)	0.0128 (15)
C29	0.076 (3)	0.082 (3)	0.083 (3)	0.006 (2)	0.011 (2)	0.048 (2)

Geometric parameters (Å, º) top

O8—N7	1.229 (5)	C23—C28	1.406 (5)
O9—N7	1.213 (4)	C24—C25	1.379 (5)
O11—C10	1.376 (3)	C25—C26	1.385 (5)
O11—C12	1.381 (4)	C26—C27	1.384 (5)
O19—C17	1.236 (4)	C26—C29	1.507 (6)
N7—C5	1.461 (5)	C27—C28	1.380 (5)
N16—N20	1.390 (3)	C1—H1	0.9300
N16—C15	1.487 (4)	C2—H2	0.9300
N16—C17	1.361 (4)	C3—H3	0.9300
N20—C21	1.294 (4)	C4—H4	0.9300
C1—C2	1.362 (6)	C13—H13	0.9300
C1—C6	1.396 (5)	C14—H14	0.9300
C2—C3	1.378 (6)	C15—H15	0.9800
C3—C4	1.367 (6)	C18—H18A	0.9600
C4—C5	1.376 (5)	C18—H18B	0.9600
C5—C6	1.393 (4)	C18—H18C	0.9600
C6—C10	1.454 (4)	C22—H22A	0.9700
C10—C14	1.353 (4)	C22—H22B	0.9700
C12—C13	1.346 (4)	C24—H24	0.9300
C12—C15	1.480 (4)	C25—H25	0.9300
C13—C14	1.418 (5)	C27—H27	0.9300
C15—C22	1.531 (4)	C28—H28	0.9300
C17—C18	1.490 (5)	C29—H29A	0.9600
C21—C22	1.499 (4)	C29—H29B	0.9600
C21—C23	1.458 (4)	C29—H29C	0.9600
C23—C24	1.383 (5)

C10—O11—C12	106.9 (2)	C27—C26—C29	121.3 (4)
O8—N7—O9	123.2 (4)	C26—C27—C28	121.9 (4)
O8—N7—C5	119.1 (3)	C23—C28—C27	120.1 (3)
O9—N7—C5	117.7 (4)	C2—C1—H1	119.00
N20—N16—C15	113.1 (2)	C6—C1—H1	119.00
N20—N16—C17	121.9 (2)	C1—C2—H2	120.00
C15—N16—C17	124.3 (2)	C3—C2—H2	120.00
N16—N20—C21	108.1 (2)	C2—C3—H3	120.00
C2—C1—C6	121.8 (3)	C4—C3—H3	120.00
C1—C2—C3	120.5 (4)	C3—C4—H4	120.00
C2—C3—C4	119.9 (4)	C5—C4—H4	120.00
C3—C4—C5	119.0 (3)	C12—C13—H13	126.00
N7—C5—C4	116.3 (3)	C14—C13—H13	126.00
N7—C5—C6	120.8 (3)	C10—C14—H14	127.00
C4—C5—C6	122.9 (3)	C13—C14—H14	127.00
C1—C6—C5	115.9 (3)	N16—C15—H15	109.00
C1—C6—C10	119.2 (3)	C12—C15—H15	109.00
C5—C6—C10	124.9 (3)	C22—C15—H15	109.00
O11—C10—C6	118.5 (2)	C17—C18—H18A	109.00
O11—C10—C14	109.5 (3)	C17—C18—H18B	109.00
C6—C10—C14	132.0 (3)	C17—C18—H18C	109.00
O11—C12—C13	109.3 (3)	H18A—C18—H18B	109.00
O11—C12—C15	116.1 (2)	H18A—C18—H18C	110.00
C13—C12—C15	134.5 (3)	H18B—C18—H18C	109.00
C12—C13—C14	107.5 (3)	C15—C22—H22A	111.00
C10—C14—C13	106.8 (2)	C15—C22—H22B	111.00
N16—C15—C12	113.3 (3)	C21—C22—H22A	111.00
N16—C15—C22	101.4 (2)	C21—C22—H22B	111.00
C12—C15—C22	114.1 (3)	H22A—C22—H22B	109.00
O19—C17—N16	119.2 (3)	C23—C24—H24	120.00
O19—C17—C18	123.3 (3)	C25—C24—H24	120.00
N16—C17—C18	117.5 (2)	C24—C25—H25	119.00
N20—C21—C22	114.0 (2)	C26—C25—H25	119.00
N20—C21—C23	121.3 (2)	C26—C27—H27	119.00
C22—C21—C23	124.7 (3)	C28—C27—H27	119.00
C15—C22—C21	103.4 (2)	C23—C28—H28	120.00
C21—C23—C24	122.5 (3)	C27—C28—H28	120.00
C21—C23—C28	119.5 (3)	C26—C29—H29A	109.00
C24—C23—C28	118.0 (3)	C26—C29—H29B	109.00
C23—C24—C25	120.9 (3)	C26—C29—H29C	109.00
C24—C25—C26	121.8 (3)	H29A—C29—H29B	109.00
C25—C26—C27	117.4 (4)	H29A—C29—H29C	109.00
C25—C26—C29	121.4 (4)	H29B—C29—H29C	110.00

C12—O11—C10—C6	179.6 (3)	C1—C6—C10—O11	147.6 (3)
C12—O11—C10—C14	−0.8 (3)	C1—C6—C10—C14	−31.9 (5)
C10—O11—C12—C13	0.2 (3)	C5—C6—C10—O11	−32.0 (4)
C10—O11—C12—C15	−176.0 (3)	C5—C6—C10—C14	148.5 (4)
O8—N7—C5—C4	129.4 (3)	O11—C10—C14—C13	1.0 (4)
O8—N7—C5—C6	−47.1 (4)	C6—C10—C14—C13	−179.5 (3)
O9—N7—C5—C4	−48.9 (5)	O11—C12—C13—C14	0.4 (4)
O9—N7—C5—C6	134.6 (4)	C15—C12—C13—C14	175.6 (3)
C15—N16—N20—C21	0.7 (4)	O11—C12—C15—N16	−67.3 (3)
C17—N16—N20—C21	−169.8 (3)	O11—C12—C15—C22	48.1 (4)
N20—N16—C15—C12	121.0 (3)	C13—C12—C15—N16	117.7 (4)
N20—N16—C15—C22	−1.7 (3)	C13—C12—C15—C22	−126.9 (4)
C17—N16—C15—C12	−68.8 (4)	C12—C13—C14—C10	−0.8 (4)
C17—N16—C15—C22	168.5 (3)	N16—C15—C22—C21	1.9 (3)
N20—N16—C17—O19	176.2 (3)	C12—C15—C22—C21	−120.3 (3)
N20—N16—C17—C18	−4.7 (5)	N20—C21—C22—C15	−1.8 (4)
C15—N16—C17—O19	6.8 (5)	C23—C21—C22—C15	178.7 (3)
C15—N16—C17—C18	−174.0 (3)	N20—C21—C23—C24	1.1 (5)
N16—N20—C21—C22	0.8 (4)	N20—C21—C23—C28	−179.9 (3)
N16—N20—C21—C23	−179.7 (3)	C22—C21—C23—C24	−179.4 (3)
C6—C1—C2—C3	0.4 (6)	C22—C21—C23—C28	−0.4 (5)
C2—C1—C6—C5	−0.3 (5)	C21—C23—C24—C25	179.0 (3)
C2—C1—C6—C10	−180.0 (3)	C28—C23—C24—C25	−0.1 (5)
C1—C2—C3—C4	−0.1 (6)	C21—C23—C28—C27	−178.5 (3)
C2—C3—C4—C5	−0.3 (6)	C24—C23—C28—C27	0.6 (5)
C3—C4—C5—N7	−176.0 (3)	C23—C24—C25—C26	−0.8 (6)
C3—C4—C5—C6	0.4 (5)	C24—C25—C26—C27	1.1 (6)
N7—C5—C6—C1	176.1 (3)	C24—C25—C26—C29	−178.6 (4)
N7—C5—C6—C10	−4.2 (4)	C25—C26—C27—C28	−0.5 (6)
C4—C5—C6—C1	−0.1 (4)	C29—C26—C27—C28	179.1 (4)
C4—C5—C6—C10	179.6 (3)	C26—C27—C28—C23	−0.3 (6)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C23–C28 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O19ⁱ	0.93	2.56	3.462 (4)	162
C18—H18C···Cg4ⁱⁱ	0.96	2.69	3.595 (4)	158

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

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C23–C28 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O19ⁱ	0.93	2.56	3.462 (4)	162
C18—H18C···Cg4ⁱⁱ	0.96	2.69	3.595 (4)	158

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

Acknowledgements

The authors thank the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. VN is grateful to the UGC, New Delhi, for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41–882/2012 (SR) dated 01/07/2012].

References

Amir, M., Kumar, H. & Khan, S. A. (2008). Bioorg. Med. Chem. Lett. 18, 918–922. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Husain, K., Abid, M. & Azam, A. (2008). Eur. J. Med. Chem. 43, 393–403. Web of Science CrossRef PubMed CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 10| October 2013| Page o1528

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

1-{3-(4-Methyl­phen­yl)-5-[5-(2-nitro­phen­yl)furan-2-yl]-4,5-di­hydro-1H-pyrazol-1-yl}ethanone

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organic compounds

1-{3-(4-Methylphenyl)-5-[5-(2-nitrophenyl)furan-2-yl]-4,5-dihydro-1H-pyrazol-1-yl}ethanone