(4-Methyl-phen-yl)[1-(4-methyl-phen-yl)-3-(5-nitro-2-fur-yl)-1H-pyrazol-4-yl]methanone.

In the title pyrazole compound, C(22)H(17)N(3)O(4), an intra-molecular 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 methyl-phenyl groups is inclined to the pyrazole ring, as indicated by the dihedral angle of 48.41 (9)°. In the crystal structure, mol-ecules are linked into chains along [10] by C-H⋯O contacts. The crystal structure is further stabilized by π-π inter-actions [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 = 387.39

Triclinic,

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 (; 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[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.144

S = 1.08

5261 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.29 e Å−3

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 ▶).

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

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

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

C22H17N3O4	Z = 2
Mr = 387.39	F(000) = 404
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0554P)2 + 0.6909P] where P = (Fo2 + 2Fc2)/3
5261 reflections	(Δ/σ)max < 0.001
264 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .