1-{3-(4-Methyl-phen-yl)-5-[5-(2-nitro-phen-yl)furan-2-yl]-4,5-di-hydro-1H-pyrazol-1-yl}ethanone.

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 R 2 (2)(16) loops. In addition, weak C-H⋯π and aromatic π-π stacking [minimum centroid-centroid distance = 3.5374 (17) Å] inter-actions 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 = 389.40

Triclinic,

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[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.242

S = 1.06

3083 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.38 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024690/hb7133sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024690/hb7133Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H19N3O4	Z = 2
Mr = 389.40	F(000) = 408
Triclinic, P1	Dx = 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

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	Rint = 0.138
Detector resolution: 10.7 pixels mm-1	θmax = 64.8°, θmin = 3.5°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→12
Tmin = 0.842, Tmax = 0.854	l = −14→15
10640 measured reflections

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(Fo2) + (0.1607P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3083 reflections	Δρmax = 0.40 e Å−3
265 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .