(4-Methyl­phen­yl)[1-(4-methyl­phen­yl)-3-(5-nitro-2-fur­yl)-1H-pyrazol-4-yl]methanone

Goh, J.H.; Fun, H.-K.; Nithinchandra; Rai, N.S.; Kalluraya, B.

doi:10.1107/S1600536809047758

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3099-o3100

doi:10.1107/S1600536809047758

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(4-Methylphenyl)[1-(4-methylphenyl)-3-(5-nitro-2-furyl)-1H-pyrazol-4-yl]methanone

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ Nithinchandra,^b N. Satheesh Rai ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 10 November 2009; accepted 11 November 2009; online 14 November 2009)

In the title pyrazole compound, C₂₂H₁₇N₃O₄, an intramolecular C—H⋯O contact generates a seven-membered ring, producing an S(7) ring motif. The furan and pyrazole rings are essentially planar [maximum deviations = 0.004 (1) and 0.004 (2) Å, respectively] and are almost coplanar, making a dihedral angle of 3.75 (10)°. One of the methylphenyl groups is inclined to the pyrazole ring, as indicated by the dihedral angle of 48.41 (9)°. In the crystal structure, molecules are linked into chains along [ $[\overline{1}]$ 10] by C—H⋯O contacts. The crystal structure is further stabilized by π–π interactions [centroid–centroid distance = 3.4437 (10) Å].

Related literature

For general background to and applications of the title compound, see: Kalluraya et al. (1994 ); Rai & Kalluraya (2006 ); Rai et al. (2008 ); Sridhar & Perumal (2003 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For a closely related structure, see: Goh et al. (2009 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₁₇N₃O₄
M_r = 387.39
Triclinic, $[P \overline 1]$
a = 9.6398 (2) Å
b = 9.9160 (2) Å
c = 10.1815 (2) Å
α = 88.051 (1)°
β = 85.930 (1)°
γ = 70.495 (1)°
V = 915.01 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.39 × 0.23 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.963, T_max = 0.989
21316 measured reflections
5261 independent reflections
4131 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.144
S = 1.08
5261 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2	0.93	2.28	2.940 (2)	128
C14—H14A⋯O3ⁱ	0.93	2.42	3.352 (2)	175
Symmetry code: (i) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL nd PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047758/tk2571sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047758/tk2571Isup2.hkl

checkCIF report

Comment top

Pyrazole derivatives are in general well-known nitrogen-containing heterocyclic compounds and various procedures have been developed for their syntheses (Rai & Kalluraya, 2006). The chemistry of pyrazole derivatives has been the subject of much interest due to their importance for various applications, and their widespread potential and proven biological and pharmacological activities (Rai et al., 2008). Steroids containing pyrazole moiety are of interest as psychopharmacological agents. Some alkyl- and aryl-substituted pyrazoles have a sharply pronounced sedative action on the central nervous system. Further, certain alkyl pyrazoles show significant bacteriostatic, bacteriocidal and fungicidal, analgesic and anti-pyretic activities (Sridhar & Perumal, 2003). In continuation of our studies on 1,3-dipolar cyclo-addition reactions of sydnones with dipolarophiles carrying a nitrofuran or nitrothiophene moiety (Kalluraya et al., 1994), we herein report the synthesis of this new pyrazole possessing 5-nitrofuran nucleus, (I).

In (I), an intramolecular C11—H11A···O2 contact (Table 1) generates a seven-membered ring, producing an S(7) ring motif (Fig. 1, Bernstein et al., 1995). The furan (C10-C13/O1) and pyrazole (C8/C9/N2/N1/C14) rings are essentially planar, with maximum deviations of -0.004 (1) and 0.004 (2) Å, respectively, for atoms O1 and C9. These two rings are almost co-planar to one another, making a dihedral angle of 3.75 (10) °. One of the methylbenzene moieties (C1-C6/C21) is inclined to the pyrazole ring, as indicated by the dihedral angle formed between the mean plane through C1-C6/C21 and the C8/C9/N2/N1/C14 pyrazole ring of 48.41 (9) °. The bond lengths and angles observed are comparable to a closely related structure (Goh et al., 2009).

In the crystal structure (Fig. 2), molecules are linked into a 1-D chain along the [110] direction by C14—H14A···O3 contacts (Table 1). The crystal structure is further stabilized by π–π interactions [Cg1···Cg1 = 3.4437 (10) Å; Cg1 is the centroid of the C8/C9/N2/N1/C14 pyrazole ring].

Related literature top

For general background to and applications of the title compound, see: Kalluraya et al. (1994); Rai & Kalluraya (2006); Rai et al. (2008); Sridhar & Perumal (2003). For hydrogen-bond motifs, see: Bernstein et al. (1995). For a closely related structure, see: Goh et al. (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

3-(p-methylphenyl)sydnone (0.01 mol) and 1-(p-methylphenyl)-3-(5-nitro-2-furyl)-2-propyn-1-one (0.01 mol) were dissolved in dry xylene (10 ml) and refluxed for 4 h. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product obtained was purified by recrystallization from ethanol and DMF mixture. The solid obtained was collected by filtration, washed with ethanol and dried. Single crystals were obtained by by slow evaporation of a DMF and ethanol (1:2) solution of (I).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. An intramolecular C–H···O contact is shown as dashed line.
	Fig. 2. A view of the crystal structure of (I), down the c axis, showing 1-D chains along the [110] direction. Intermolecular C–H···O contacts are shown as dashed lines.

(4-Methylphenyl)[1-(4-methylphenyl)-3-(5-nitro-2-furyl)-1H-pyrazol- 4-yl]methanone top

Crystal data top

C₂₂H₁₇N₃O₄	Z = 2
M_r = 387.39	F(000) = 404
Triclinic, P1	D_x = 1.406 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6398 (2) Å	Cell parameters from 9115 reflections
b = 9.9160 (2) Å	θ = 2.2–29.9°
c = 10.1815 (2) Å	µ = 0.10 mm⁻¹
α = 88.051 (1)°	T = 100 K
β = 85.930 (1)°	Block, orange
γ = 70.495 (1)°	0.39 × 0.23 × 0.11 mm
V = 915.01 (3) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5261 independent reflections
Radiation source: fine-focus sealed tube	4131 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 29.9°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.963, T_max = 0.989	k = −13→13
21316 measured reflections	l = −14→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0554P)² + 0.6909P] where P = (F_o² + 2F_c²)/3
5261 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₂H₁₇N₃O₄	γ = 70.495 (1)°
M_r = 387.39	V = 915.01 (3) Å³
Triclinic, P1	Z = 2
a = 9.6398 (2) Å	Mo Kα radiation
b = 9.9160 (2) Å	µ = 0.10 mm⁻¹
c = 10.1815 (2) Å	T = 100 K
α = 88.051 (1)°	0.39 × 0.23 × 0.11 mm
β = 85.930 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5261 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4131 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.989	R_int = 0.032
21316 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.08	Δρ_max = 0.51 e Å⁻³
5261 reflections	Δρ_min = −0.29 e Å⁻³
264 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
O1	0.37746 (12)	−0.18217 (11)	0.54625 (12)	0.0192 (3)
O2	0.27874 (13)	0.22439 (13)	0.28781 (12)	0.0220 (3)
O3	0.71075 (14)	−0.45933 (13)	0.52077 (13)	0.0275 (3)
O4	0.51656 (15)	−0.43098 (14)	0.65457 (15)	0.0329 (3)
N1	−0.00353 (15)	0.13036 (14)	0.62991 (13)	0.0165 (3)
N2	0.12266 (15)	0.01582 (14)	0.61610 (14)	0.0173 (3)
N3	0.58353 (16)	−0.39214 (15)	0.56224 (15)	0.0218 (3)
C1	−0.11237 (18)	0.36641 (17)	0.26082 (16)	0.0190 (3)
H1A	−0.1398	0.2924	0.3004	0.023*
C2	−0.21404 (19)	0.47566 (19)	0.19334 (17)	0.0221 (4)
H2A	−0.3088	0.4727	0.1870	0.026*
C3	−0.17692 (19)	0.58885 (18)	0.13536 (17)	0.0227 (4)
C4	−0.03428 (19)	0.59078 (18)	0.14428 (17)	0.0227 (4)
H4A	−0.0079	0.6663	0.1067	0.027*
C5	0.06906 (19)	0.48115 (17)	0.20874 (17)	0.0206 (3)
H5A	0.1647	0.4827	0.2121	0.025*
C6	0.03091 (18)	0.36868 (16)	0.26861 (16)	0.0171 (3)
C7	0.15071 (18)	0.25230 (16)	0.33197 (16)	0.0169 (3)
C8	0.11205 (17)	0.17708 (16)	0.44824 (16)	0.0162 (3)
C9	0.19410 (17)	0.04329 (16)	0.50694 (16)	0.0160 (3)
C10	0.33574 (18)	−0.06208 (16)	0.46636 (16)	0.0167 (3)
C11	0.44312 (18)	−0.06981 (17)	0.36922 (16)	0.0202 (3)
H11A	0.4408	−0.0024	0.3029	0.024*
C12	0.55914 (19)	−0.20056 (17)	0.38871 (17)	0.0209 (3)
H12A	0.6478	−0.2365	0.3386	0.025*
C13	0.51276 (18)	−0.26116 (16)	0.49567 (17)	0.0192 (3)
C14	−0.01294 (18)	0.22782 (16)	0.53221 (16)	0.0170 (3)
H14A	−0.0897	0.3137	0.5230	0.020*
C15	−0.10373 (17)	0.13658 (16)	0.74182 (16)	0.0164 (3)
C16	−0.07593 (19)	0.02085 (18)	0.82857 (17)	0.0216 (3)
H16A	0.0039	−0.0619	0.8115	0.026*
C17	−0.1685 (2)	0.03015 (19)	0.94092 (18)	0.0246 (4)
H17A	−0.1504	−0.0482	0.9980	0.029*
C18	−0.28747 (19)	0.1528 (2)	0.97094 (17)	0.0227 (4)
C19	−0.31491 (19)	0.26609 (18)	0.88030 (17)	0.0225 (4)
H19A	−0.3948	0.3488	0.8973	0.027*
C20	−0.22600 (18)	0.25837 (17)	0.76544 (17)	0.0194 (3)
H20A	−0.2480	0.3338	0.7050	0.023*
C21	−0.2876 (2)	0.7069 (2)	0.0625 (2)	0.0360 (5)
H21A	−0.2859	0.7979	0.0900	0.054*
H21B	−0.3844	0.7011	0.0816	0.054*
H21C	−0.2628	0.6967	−0.0305	0.054*
C22	−0.3809 (2)	0.1612 (2)	1.09795 (19)	0.0325 (5)
H22A	−0.3183	0.1206	1.1685	0.049*
H22B	−0.4475	0.1089	1.0894	0.049*
H22C	−0.4363	0.2595	1.1167	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0163 (6)	0.0132 (5)	0.0240 (6)	0.0000 (4)	0.0004 (4)	0.0034 (4)
O2	0.0183 (6)	0.0197 (6)	0.0252 (6)	−0.0038 (5)	0.0025 (5)	0.0048 (5)
O3	0.0230 (6)	0.0198 (6)	0.0288 (7)	0.0067 (5)	0.0010 (5)	−0.0002 (5)
O4	0.0273 (7)	0.0218 (6)	0.0426 (8)	−0.0017 (5)	0.0048 (6)	0.0128 (6)
N1	0.0154 (6)	0.0126 (6)	0.0187 (7)	−0.0015 (5)	0.0008 (5)	0.0015 (5)
N2	0.0149 (6)	0.0121 (6)	0.0216 (7)	−0.0004 (5)	−0.0003 (5)	0.0007 (5)
N3	0.0208 (7)	0.0152 (6)	0.0251 (8)	−0.0003 (5)	−0.0016 (6)	0.0004 (5)
C1	0.0196 (8)	0.0170 (7)	0.0191 (8)	−0.0052 (6)	0.0016 (6)	0.0035 (6)
C2	0.0166 (8)	0.0251 (8)	0.0218 (8)	−0.0040 (6)	−0.0001 (6)	0.0048 (7)
C3	0.0198 (8)	0.0226 (8)	0.0198 (8)	−0.0003 (6)	0.0008 (6)	0.0064 (6)
C4	0.0242 (8)	0.0173 (7)	0.0246 (9)	−0.0053 (6)	−0.0002 (7)	0.0069 (6)
C5	0.0206 (8)	0.0179 (7)	0.0223 (8)	−0.0055 (6)	−0.0013 (6)	0.0029 (6)
C6	0.0184 (7)	0.0138 (7)	0.0169 (7)	−0.0028 (6)	−0.0004 (6)	0.0016 (6)
C7	0.0192 (8)	0.0134 (7)	0.0172 (7)	−0.0045 (6)	0.0001 (6)	0.0019 (6)
C8	0.0163 (7)	0.0122 (6)	0.0186 (8)	−0.0029 (5)	−0.0015 (6)	0.0015 (5)
C9	0.0169 (7)	0.0122 (6)	0.0176 (7)	−0.0032 (5)	−0.0009 (6)	0.0011 (5)
C10	0.0177 (7)	0.0117 (6)	0.0191 (8)	−0.0028 (6)	−0.0029 (6)	0.0013 (5)
C11	0.0210 (8)	0.0165 (7)	0.0186 (8)	−0.0007 (6)	−0.0006 (6)	0.0014 (6)
C12	0.0187 (8)	0.0182 (7)	0.0205 (8)	0.0008 (6)	0.0002 (6)	−0.0023 (6)
C13	0.0168 (8)	0.0138 (7)	0.0223 (8)	0.0010 (6)	−0.0009 (6)	−0.0005 (6)
C14	0.0175 (7)	0.0126 (6)	0.0189 (8)	−0.0024 (6)	−0.0010 (6)	0.0023 (5)
C15	0.0159 (7)	0.0155 (7)	0.0174 (7)	−0.0048 (6)	−0.0003 (6)	0.0001 (6)
C16	0.0211 (8)	0.0176 (7)	0.0227 (8)	−0.0026 (6)	−0.0003 (6)	0.0037 (6)
C17	0.0242 (9)	0.0257 (8)	0.0226 (9)	−0.0077 (7)	−0.0009 (7)	0.0079 (7)
C18	0.0197 (8)	0.0304 (9)	0.0183 (8)	−0.0090 (7)	0.0004 (6)	0.0013 (7)
C19	0.0174 (8)	0.0221 (8)	0.0251 (9)	−0.0032 (6)	0.0017 (6)	−0.0015 (7)
C20	0.0182 (8)	0.0152 (7)	0.0229 (8)	−0.0036 (6)	0.0004 (6)	0.0028 (6)
C21	0.0218 (9)	0.0388 (11)	0.0377 (11)	0.0001 (8)	0.0009 (8)	0.0226 (9)
C22	0.0253 (10)	0.0465 (12)	0.0210 (9)	−0.0070 (8)	0.0033 (7)	0.0053 (8)

Geometric parameters (Å, º) top

O1—C13	1.3526 (18)	C9—C10	1.457 (2)
O1—C10	1.3792 (18)	C10—C11	1.365 (2)
O2—C7	1.2262 (19)	C11—C12	1.420 (2)
O3—N3	1.2354 (18)	C11—H11A	0.9300
O4—N3	1.2264 (19)	C12—C13	1.346 (2)
N1—C14	1.349 (2)	C12—H12A	0.9300
N1—N2	1.3614 (17)	C14—H14A	0.9300
N1—C15	1.430 (2)	C15—C16	1.389 (2)
N2—C9	1.334 (2)	C15—C20	1.391 (2)
N3—C13	1.423 (2)	C16—C17	1.386 (2)
C1—C2	1.394 (2)	C16—H16A	0.9300
C1—C6	1.397 (2)	C17—C18	1.390 (2)
C1—H1A	0.9300	C17—H17A	0.9300
C2—C3	1.389 (2)	C18—C19	1.396 (2)
C2—H2A	0.9300	C18—C22	1.511 (2)
C3—C4	1.391 (3)	C19—C20	1.389 (2)
C3—C21	1.509 (2)	C19—H19A	0.9300
C4—C5	1.388 (2)	C20—H20A	0.9300
C4—H4A	0.9300	C21—H21A	0.9600
C5—C6	1.395 (2)	C21—H21B	0.9600
C5—H5A	0.9300	C21—H21C	0.9600
C6—C7	1.499 (2)	C22—H22A	0.9600
C7—C8	1.470 (2)	C22—H22B	0.9600
C8—C14	1.383 (2)	C22—H22C	0.9600
C8—C9	1.434 (2)

C13—O1—C10	104.73 (12)	C12—C11—H11A	126.6
C14—N1—N2	112.14 (13)	C13—C12—C11	104.92 (14)
C14—N1—C15	128.60 (13)	C13—C12—H12A	127.5
N2—N1—C15	119.22 (13)	C11—C12—H12A	127.5
C9—N2—N1	105.09 (12)	C12—C13—O1	113.27 (14)
O4—N3—O3	124.62 (14)	C12—C13—N3	130.32 (15)
O4—N3—C13	119.26 (14)	O1—C13—N3	116.41 (14)
O3—N3—C13	116.12 (14)	N1—C14—C8	107.72 (13)
C2—C1—C6	119.62 (15)	N1—C14—H14A	126.1
C2—C1—H1A	120.2	C8—C14—H14A	126.1
C6—C1—H1A	120.2	C16—C15—C20	120.22 (15)
C3—C2—C1	121.40 (16)	C16—C15—N1	119.28 (14)
C3—C2—H2A	119.3	C20—C15—N1	120.49 (14)
C1—C2—H2A	119.3	C17—C16—C15	119.23 (15)
C2—C3—C4	118.62 (15)	C17—C16—H16A	120.4
C2—C3—C21	121.14 (17)	C15—C16—H16A	120.4
C4—C3—C21	120.24 (16)	C16—C17—C18	122.08 (16)
C5—C4—C3	120.63 (16)	C16—C17—H17A	119.0
C5—C4—H4A	119.7	C18—C17—H17A	119.0
C3—C4—H4A	119.7	C17—C18—C19	117.40 (16)
C4—C5—C6	120.65 (16)	C17—C18—C22	120.35 (16)
C4—C5—H5A	119.7	C19—C18—C22	122.25 (16)
C6—C5—H5A	119.7	C20—C19—C18	121.69 (15)
C5—C6—C1	119.07 (15)	C20—C19—H19A	119.2
C5—C6—C7	117.08 (15)	C18—C19—H19A	119.2
C1—C6—C7	123.77 (14)	C19—C20—C15	119.28 (15)
O2—C7—C8	121.55 (14)	C19—C20—H20A	120.4
O2—C7—C6	119.45 (14)	C15—C20—H20A	120.4
C8—C7—C6	118.98 (14)	C3—C21—H21A	109.5
C14—C8—C9	103.84 (13)	C3—C21—H21B	109.5
C14—C8—C7	126.10 (14)	H21A—C21—H21B	109.5
C9—C8—C7	129.94 (14)	C3—C21—H21C	109.5
N2—C9—C8	111.20 (13)	H21A—C21—H21C	109.5
N2—C9—C10	117.80 (13)	H21B—C21—H21C	109.5
C8—C9—C10	131.00 (15)	C18—C22—H22A	109.5
C11—C10—O1	110.18 (13)	C18—C22—H22B	109.5
C11—C10—C9	135.41 (15)	H22A—C22—H22B	109.5
O1—C10—C9	114.36 (13)	C18—C22—H22C	109.5
C10—C11—C12	106.90 (14)	H22A—C22—H22C	109.5
C10—C11—H11A	126.6	H22B—C22—H22C	109.5

C14—N1—N2—C9	0.31 (18)	C8—C9—C10—O1	−177.61 (16)
C15—N1—N2—C9	−177.78 (14)	O1—C10—C11—C12	−0.40 (19)
C6—C1—C2—C3	−1.2 (3)	C9—C10—C11—C12	176.65 (19)
C1—C2—C3—C4	0.8 (3)	C10—C11—C12—C13	0.0 (2)
C1—C2—C3—C21	−179.96 (17)	C11—C12—C13—O1	0.4 (2)
C2—C3—C4—C5	0.6 (3)	C11—C12—C13—N3	−179.11 (18)
C21—C3—C4—C5	−178.65 (17)	C10—O1—C13—C12	−0.66 (19)
C3—C4—C5—C6	−1.6 (3)	C10—O1—C13—N3	178.94 (14)
C4—C5—C6—C1	1.1 (2)	O4—N3—C13—C12	−175.80 (19)
C4—C5—C6—C7	177.95 (15)	O3—N3—C13—C12	4.0 (3)
C2—C1—C6—C5	0.2 (2)	O4—N3—C13—O1	4.7 (2)
C2—C1—C6—C7	−176.34 (15)	O3—N3—C13—O1	−175.53 (15)
C5—C6—C7—O2	−29.8 (2)	N2—N1—C14—C8	0.17 (19)
C1—C6—C7—O2	146.86 (17)	C15—N1—C14—C8	178.05 (15)
C5—C6—C7—C8	148.48 (16)	C9—C8—C14—N1	−0.54 (18)
C1—C6—C7—C8	−34.9 (2)	C7—C8—C14—N1	−176.89 (15)
O2—C7—C8—C14	156.53 (17)	C14—N1—C15—C16	177.34 (17)
C6—C7—C8—C14	−21.7 (3)	N2—N1—C15—C16	−4.9 (2)
O2—C7—C8—C9	−18.8 (3)	C14—N1—C15—C20	−4.1 (3)
C6—C7—C8—C9	162.94 (16)	N2—N1—C15—C20	173.63 (15)
N1—N2—C9—C8	−0.67 (18)	C20—C15—C16—C17	−2.2 (3)
N1—N2—C9—C10	179.90 (14)	N1—C15—C16—C17	176.38 (16)
C14—C8—C9—N2	0.77 (19)	C15—C16—C17—C18	−1.0 (3)
C7—C8—C9—N2	176.92 (16)	C16—C17—C18—C19	2.6 (3)
C14—C8—C9—C10	−179.89 (17)	C16—C17—C18—C22	−176.83 (18)
C7—C8—C9—C10	−3.7 (3)	C17—C18—C19—C20	−1.0 (3)
C13—O1—C10—C11	0.64 (18)	C22—C18—C19—C20	178.38 (18)
C13—O1—C10—C9	−177.09 (14)	C18—C19—C20—C15	−2.0 (3)
N2—C9—C10—C11	−175.27 (19)	C16—C15—C20—C19	3.7 (3)
C8—C9—C10—C11	5.4 (3)	N1—C15—C20—C19	−174.87 (16)
N2—C9—C10—O1	1.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2	0.93	2.28	2.940 (2)	128
C14—H14A···O3ⁱ	0.93	2.42	3.352 (2)	175

Symmetry code: (i) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇N₃O₄
M_r	387.39
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.6398 (2), 9.9160 (2), 10.1815 (2)
α, β, γ (°)	88.051 (1), 85.930 (1), 70.495 (1)
V (Å³)	915.01 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.39 × 0.23 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.963, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	21316, 5261, 4131
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.701

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.144, 1.08
No. of reflections	5261
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.29

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2	0.93	2.28	2.940 (2)	128
C14—H14A···O3ⁱ	0.93	2.42	3.352 (2)	175

Symmetry code: (i) x−1, y+1, z.

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra & Kalluraya, B. (2009). Acta Cryst. E65, o3088–o3089. Google Scholar
Kalluraya, B., D'Souza, A. & Holla, B. S. (1994). Indian J. Chem. Sect. B, 33, 1017–1022. Google Scholar
Rai, N. S. & Kalluraya, B. (2006). Indian J. Chem. Sect. B, 46, 375–378. Google Scholar
Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715–1720. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sridhar, R. & Perumal, P. T. (2003). Synth. Commun. 33, 1483–1488. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 12| December 2009| Pages o3099-o3100

doi:10.1107/S1600536809047758

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

(4-Methyl­phen­yl)[1-(4-methyl­phen­yl)-3-(5-nitro-2-fur­yl)-1H-pyrazol-4-yl]methanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

(4-Methylphenyl)[1-(4-methylphenyl)-3-(5-nitro-2-furyl)-1H-pyrazol-4-yl]methanone