[3-(5-Nitro-2-fur-yl)-1-phenyl-1H-pyrazol-4-yl](phen-yl)methanone.

In the title pyrazole compound, C(20)H(13)N(3)O(4), an intra-molecular C-H⋯O hydrogen bond generates a seven-membered ring, producing an S(7) ring motif. The essentially planar furan and pyrazole rings [maximum deviations of 0.002 (1) and 0.007 (1) Å, respectively] are coplanar with each other, forming a dihedral angle of 3.06 (10)°. The pyrazole ring forms dihedral angles of 8.51 (9) and 56.81 (9)° with the two benzene rings. The nitro group is coplanar with the attached furan ring, as indicated by the dihedral angle of 2.5 (3)°. In the crystal packing, inter-molecular C-H⋯O hydrogen bonds link adjacent mol-ecules into two-mol-ecule-wide chains along the a axis. The crystal packing is further stabilized by weak inter-molecular C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.4441 (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 graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For closely related structures, see: Goh et al. (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H13N3O4

M = 359.33

Monoclinic,

a = 11.2946 (12) Å

b = 6.9755 (8) Å

c = 22.7064 (18) Å

β = 115.015 (4)°

V = 1621.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.24 × 0.15 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.976, T max = 0.992

17931 measured reflections

4725 independent reflections

2991 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.129

S = 1.02

4725 reflections

296 parameters

All H-atom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015199/tk2653sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015199/tk2653Isup2.hkl

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

C20H13N3O4	F(000) = 744
Mr = 359.33	Dx = 1.472 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2349 reflections
a = 11.2946 (12) Å	θ = 3.5–26.3°
b = 6.9755 (8) Å	µ = 0.11 mm−1
c = 22.7064 (18) Å	T = 100 K
β = 115.015 (4)°	Block, brown
V = 1621.1 (3) Å3	0.24 × 0.15 × 0.07 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	4725 independent reflections
Radiation source: fine-focus sealed tube	2991 reflections with I > 2σ(I)
graphite	Rint = 0.056
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.976, Tmax = 0.992	k = −9→9
17931 measured reflections	l = −31→31

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	All H-atom parameters refined
S = 1.02	w = 1/[σ2(Fo2) + (0.0464P)2 + 0.6127P] where P = (Fo2 + 2Fc2)/3
4725 reflections	(Δ/σ)max = 0.001
296 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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	1.26743 (11)	0.74226 (19)	1.00753 (6)	0.0293 (3)
O2	0.86733 (12)	0.95863 (19)	0.85528 (6)	0.0297 (3)
O3	1.55123 (13)	0.7939 (2)	0.98584 (7)	0.0411 (4)
O4	1.52027 (15)	0.6888 (3)	1.06817 (9)	0.0764 (7)
N1	0.96246 (13)	0.6915 (2)	1.05307 (6)	0.0206 (3)
N2	1.07625 (13)	0.6992 (2)	1.04603 (7)	0.0215 (3)
N3	1.48065 (16)	0.7520 (3)	1.01308 (9)	0.0382 (4)
C1	0.62475 (17)	0.6603 (3)	0.86532 (8)	0.0286 (4)
C2	0.49042 (19)	0.6327 (4)	0.83427 (9)	0.0359 (5)
C3	0.40950 (19)	0.7816 (4)	0.80076 (9)	0.0410 (5)
C4	0.4611 (2)	0.9603 (4)	0.79806 (10)	0.0434 (6)
C5	0.5954 (2)	0.9876 (3)	0.82757 (10)	0.0362 (5)
C6	0.67801 (17)	0.8374 (3)	0.86116 (8)	0.0271 (4)
C7	0.82209 (16)	0.8692 (3)	0.88763 (8)	0.0238 (4)
C8	0.90414 (16)	0.7934 (2)	0.95280 (8)	0.0213 (3)
C9	1.04207 (16)	0.7631 (2)	0.98559 (8)	0.0208 (3)
C10	1.14371 (16)	0.7910 (2)	0.96325 (8)	0.0226 (4)
C11	1.14713 (18)	0.8593 (3)	0.90780 (9)	0.0278 (4)
C12	1.27856 (18)	0.8549 (3)	0.91693 (9)	0.0294 (4)
C13	1.34517 (17)	0.7833 (3)	0.97709 (9)	0.0282 (4)
C14	0.85851 (16)	0.7448 (2)	0.99826 (8)	0.0216 (3)
C15	0.96295 (16)	0.6275 (2)	1.11294 (8)	0.0209 (3)
C16	1.07647 (16)	0.5522 (3)	1.16079 (8)	0.0233 (4)
C17	1.07388 (18)	0.4800 (3)	1.21724 (9)	0.0281 (4)
C18	0.96039 (18)	0.4857 (3)	1.22655 (9)	0.0282 (4)
C19	0.84901 (18)	0.5655 (3)	1.17896 (9)	0.0273 (4)
C20	0.84850 (17)	0.6368 (3)	1.12181 (8)	0.0238 (4)
H1A	0.6830 (18)	0.558 (3)	0.8899 (9)	0.024 (5)*
H2A	0.458 (2)	0.505 (3)	0.8376 (11)	0.047 (7)*
H3A	0.315 (2)	0.757 (3)	0.7776 (11)	0.047 (6)*
H4A	0.406 (2)	1.071 (4)	0.7748 (12)	0.057 (7)*
H5A	0.635 (2)	1.110 (4)	0.8263 (11)	0.048 (7)*
H11A	1.071 (2)	0.900 (4)	0.8687 (12)	0.061 (7)*
H12A	1.319 (2)	0.895 (3)	0.8890 (10)	0.041 (6)*
H14A	0.7722 (19)	0.741 (3)	0.9963 (9)	0.028 (5)*
H16A	1.1530 (18)	0.549 (3)	1.1519 (9)	0.025 (5)*
H17A	1.150 (2)	0.425 (3)	1.2493 (10)	0.039 (6)*
H18A	0.9566 (19)	0.433 (3)	1.2648 (10)	0.034 (5)*
H19A	0.7709 (17)	0.575 (3)	1.1840 (8)	0.022 (5)*
H20A	0.7707 (18)	0.686 (3)	1.0903 (9)	0.022 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0199 (6)	0.0361 (7)	0.0344 (7)	0.0003 (5)	0.0140 (5)	0.0054 (6)
O2	0.0304 (7)	0.0320 (7)	0.0293 (6)	−0.0019 (6)	0.0152 (5)	0.0027 (6)
O3	0.0260 (7)	0.0555 (10)	0.0492 (8)	−0.0051 (7)	0.0230 (6)	−0.0074 (7)
O4	0.0283 (8)	0.1271 (18)	0.0727 (12)	0.0171 (10)	0.0201 (8)	0.0604 (13)
N1	0.0185 (7)	0.0227 (7)	0.0226 (7)	−0.0021 (6)	0.0106 (5)	−0.0021 (6)
N2	0.0184 (6)	0.0232 (7)	0.0252 (7)	−0.0015 (6)	0.0115 (5)	−0.0030 (6)
N3	0.0244 (8)	0.0450 (11)	0.0475 (10)	0.0010 (7)	0.0176 (7)	0.0061 (9)
C1	0.0235 (9)	0.0393 (11)	0.0230 (8)	0.0008 (8)	0.0098 (7)	0.0008 (8)
C2	0.0274 (10)	0.0548 (14)	0.0264 (9)	−0.0065 (10)	0.0125 (8)	−0.0022 (10)
C3	0.0222 (9)	0.0738 (17)	0.0254 (9)	0.0009 (10)	0.0086 (8)	0.0023 (10)
C4	0.0268 (10)	0.0670 (16)	0.0350 (10)	0.0134 (11)	0.0116 (8)	0.0175 (11)
C5	0.0324 (10)	0.0443 (13)	0.0337 (10)	0.0069 (10)	0.0157 (8)	0.0113 (9)
C6	0.0240 (8)	0.0385 (11)	0.0205 (8)	0.0027 (8)	0.0110 (7)	0.0013 (8)
C7	0.0255 (8)	0.0242 (9)	0.0232 (8)	0.0008 (7)	0.0117 (7)	−0.0024 (7)
C8	0.0214 (8)	0.0199 (8)	0.0242 (8)	−0.0021 (7)	0.0112 (6)	−0.0029 (7)
C9	0.0216 (8)	0.0172 (8)	0.0246 (8)	−0.0027 (7)	0.0108 (6)	−0.0050 (7)
C10	0.0189 (8)	0.0216 (8)	0.0271 (8)	−0.0021 (7)	0.0095 (7)	−0.0040 (7)
C11	0.0258 (9)	0.0337 (10)	0.0276 (9)	−0.0023 (8)	0.0148 (7)	−0.0026 (8)
C12	0.0276 (9)	0.0352 (11)	0.0303 (9)	−0.0065 (8)	0.0171 (7)	−0.0070 (8)
C13	0.0193 (8)	0.0301 (10)	0.0387 (10)	−0.0020 (7)	0.0157 (7)	−0.0026 (8)
C14	0.0197 (8)	0.0214 (8)	0.0239 (8)	0.0003 (7)	0.0095 (6)	−0.0030 (7)
C15	0.0225 (8)	0.0196 (8)	0.0221 (7)	−0.0030 (7)	0.0108 (6)	−0.0027 (7)
C16	0.0207 (8)	0.0245 (9)	0.0257 (8)	−0.0017 (7)	0.0106 (7)	−0.0032 (7)
C17	0.0270 (9)	0.0287 (10)	0.0251 (8)	−0.0012 (8)	0.0077 (7)	0.0007 (8)
C18	0.0327 (10)	0.0291 (10)	0.0240 (8)	−0.0073 (8)	0.0131 (7)	−0.0024 (8)
C19	0.0254 (9)	0.0305 (10)	0.0315 (9)	−0.0041 (8)	0.0173 (7)	−0.0042 (8)
C20	0.0204 (8)	0.0248 (9)	0.0262 (8)	−0.0013 (7)	0.0099 (7)	−0.0020 (7)

O1—C13	1.358 (2)	C7—C8	1.472 (2)
O1—C10	1.375 (2)	C8—C14	1.377 (2)
O2—C7	1.228 (2)	C8—C9	1.430 (2)
O3—N3	1.233 (2)	C9—C10	1.451 (2)
O4—N3	1.219 (2)	C10—C11	1.362 (2)
N1—C14	1.353 (2)	C11—C12	1.410 (3)
N1—N2	1.3616 (18)	C11—H11A	0.98 (2)
N1—C15	1.429 (2)	C12—C13	1.346 (3)
N2—C9	1.335 (2)	C12—H12A	0.96 (2)
N3—C13	1.414 (2)	C14—H14A	0.96 (2)
C1—C2	1.390 (3)	C15—C16	1.387 (2)
C1—C6	1.395 (3)	C15—C20	1.391 (2)
C1—H1A	0.97 (2)	C16—C17	1.389 (2)
C2—C3	1.380 (3)	C16—H16A	0.968 (18)
C2—H2A	0.98 (2)	C17—C18	1.385 (3)
C3—C4	1.388 (3)	C17—H17A	0.94 (2)
C3—H3A	0.99 (2)	C18—C19	1.382 (3)
C4—C5	1.389 (3)	C18—H18A	0.96 (2)
C4—H4A	1.00 (3)	C19—C20	1.387 (2)
C5—C6	1.396 (3)	C19—H19A	0.939 (18)
C5—H5A	0.97 (2)	C20—H20A	0.933 (18)
C6—C7	1.494 (2)
C13—O1—C10	104.57 (13)	C8—C9—C10	130.30 (15)
C14—N1—N2	112.10 (13)	C11—C10—O1	110.18 (14)
C14—N1—C15	127.88 (14)	C11—C10—C9	134.91 (16)
N2—N1—C15	120.00 (13)	O1—C10—C9	114.89 (14)
C9—N2—N1	104.88 (13)	C10—C11—C12	107.23 (16)
O4—N3—O3	124.47 (17)	C10—C11—H11A	125.5 (14)
O4—N3—C13	119.14 (17)	C12—C11—H11A	127.2 (14)
O3—N3—C13	116.38 (17)	C13—C12—C11	105.03 (16)
C2—C1—C6	119.85 (19)	C13—C12—H12A	124.0 (13)
C2—C1—H1A	121.2 (11)	C11—C12—H12A	131.0 (13)
C6—C1—H1A	118.9 (11)	C12—C13—O1	112.99 (15)
C3—C2—C1	120.1 (2)	C12—C13—N3	130.37 (17)
C3—C2—H2A	123.0 (14)	O1—C13—N3	116.60 (16)
C1—C2—H2A	116.9 (13)	N1—C14—C8	107.64 (15)
C2—C3—C4	120.51 (19)	N1—C14—H14A	120.4 (11)
C2—C3—H3A	118.6 (14)	C8—C14—H14A	132.0 (11)
C4—C3—H3A	120.8 (14)	C16—C15—C20	120.80 (16)
C3—C4—C5	119.7 (2)	C16—C15—N1	119.63 (14)
C3—C4—H4A	122.8 (14)	C20—C15—N1	119.55 (15)
C5—C4—H4A	117.5 (14)	C15—C16—C17	119.16 (16)
C4—C5—C6	120.2 (2)	C15—C16—H16A	117.3 (11)
C4—C5—H5A	122.1 (13)	C17—C16—H16A	123.6 (11)
C6—C5—H5A	117.7 (14)	C18—C17—C16	120.84 (17)
C1—C6—C5	119.62 (17)	C18—C17—H17A	119.5 (13)
C1—C6—C7	122.14 (17)	C16—C17—H17A	119.6 (13)
C5—C6—C7	118.10 (18)	C19—C18—C17	119.16 (17)
O2—C7—C8	122.64 (16)	C19—C18—H18A	119.1 (12)
O2—C7—C6	119.53 (15)	C17—C18—H18A	121.7 (12)
C8—C7—C6	117.83 (15)	C18—C19—C20	121.20 (17)
C14—C8—C9	104.11 (14)	C18—C19—H19A	121.7 (11)
C14—C8—C7	124.45 (15)	C20—C19—H19A	117.1 (11)
C9—C8—C7	131.35 (15)	C19—C20—C15	118.82 (16)
N2—C9—C8	111.25 (14)	C19—C20—H20A	118.7 (11)
N2—C9—C10	118.45 (15)	C15—C20—H20A	122.5 (11)
C14—N1—N2—C9	1.32 (18)	C8—C9—C10—O1	−178.34 (16)
C15—N1—N2—C9	179.83 (15)	O1—C10—C11—C12	−0.2 (2)
C6—C1—C2—C3	−1.6 (3)	C9—C10—C11—C12	178.25 (19)
C1—C2—C3—C4	−0.4 (3)	C10—C11—C12—C13	0.3 (2)
C2—C3—C4—C5	2.1 (3)	C11—C12—C13—O1	−0.3 (2)
C3—C4—C5—C6	−1.6 (3)	C11—C12—C13—N3	−177.8 (2)
C2—C1—C6—C5	2.1 (3)	C10—O1—C13—C12	0.2 (2)
C2—C1—C6—C7	−173.56 (16)	C10—O1—C13—N3	178.07 (16)
C4—C5—C6—C1	−0.5 (3)	O4—N3—C13—C12	178.3 (2)
C4—C5—C6—C7	175.34 (18)	O3—N3—C13—C12	−0.8 (3)
C1—C6—C7—O2	135.87 (18)	O4—N3—C13—O1	0.9 (3)
C5—C6—C7—O2	−39.8 (2)	O3—N3—C13—O1	−178.27 (17)
C1—C6—C7—C8	−45.1 (2)	N2—N1—C14—C8	−1.0 (2)
C5—C6—C7—C8	139.15 (17)	C15—N1—C14—C8	−179.35 (16)
O2—C7—C8—C14	159.65 (17)	C9—C8—C14—N1	0.24 (19)
C6—C7—C8—C14	−19.3 (3)	C7—C8—C14—N1	−176.58 (16)
O2—C7—C8—C9	−16.2 (3)	C14—N1—C15—C16	170.60 (17)
C6—C7—C8—C9	164.80 (17)	N2—N1—C15—C16	−7.6 (2)
N1—N2—C9—C8	−1.14 (18)	C14—N1—C15—C20	−7.7 (3)
N1—N2—C9—C10	178.84 (14)	N2—N1—C15—C20	174.08 (15)
C14—C8—C9—N2	0.58 (19)	C20—C15—C16—C17	2.0 (3)
C7—C8—C9—N2	177.09 (17)	N1—C15—C16—C17	−176.24 (16)
C14—C8—C9—C10	−179.40 (17)	C15—C16—C17—C18	−1.1 (3)
C7—C8—C9—C10	−2.9 (3)	C16—C17—C18—C19	−0.4 (3)
C13—O1—C10—C11	0.0 (2)	C17—C18—C19—C20	1.1 (3)
C13—O1—C10—C9	−178.77 (15)	C18—C19—C20—C15	−0.2 (3)
N2—C9—C10—C11	−176.7 (2)	C16—C15—C20—C19	−1.3 (3)
C8—C9—C10—C11	3.2 (3)	N1—C15—C20—C19	176.91 (16)
N2—C9—C10—O1	1.7 (2)

Cg1 is the centroid of the C15–C20 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4i	0.98 (2)	2.45 (2)	3.190 (3)	131.8 (17)
C11—H11A···O2	0.98 (3)	2.23 (3)	2.950 (3)	130 (2)
C14—H14A···O3ii	0.96 (2)	2.43 (2)	3.379 (3)	169.3 (17)
C18—H18A···Cg1iii	0.96 (2)	2.96 (2)	3.671 (2)	132.0 (16)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4i	0.98 (2)	2.45 (2)	3.190 (3)	131.8 (17)
C11—H11A⋯O2	0.98 (3)	2.23 (3)	2.950 (3)	130 (2)
C14—H14A⋯O3ii	0.96 (2)	2.43 (2)	3.379 (3)	169.3 (17)
C18—H18A⋯Cg1iii	0.96 (2)	2.96 (2)	3.671 (2)	132.0 (16)

Symmetry codes: (i) ; (ii) ; (iii) .