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

In the title pyrazole compound, C(21)H(15)N(3)O(4), an intra-molecular C-H⋯O hydrogen bond generates an S(7) ring motif. The essentially planar furan and pyrazole rings [maximum atomic deviations of 0.011 (2) and 0.006 (2) Å, respectively] make a dihedral angle of 9.21 (11)°. The nitro group is approximately coplanar with the attached furan ring, as indicated by the dihedral angle of 4.5 (2)°. In the crystal structure, inter-molecular C-H⋯O inter-actions form bifurcated hydrogen bonds, generating R(1) (2)(7) ring motifs. These hydrogen bonds link the mol-ecules into infinite chains along the a axis. The crystal structure is further stabilized by weak inter-molecular π-π inter-actions [centroid-centroid distance = 3.4118 (10) Å].

Related literature

For general background to and applications of the title compound, see: Hegde et al. (2006 ▶); Kalluraya et al. (1994 ▶); Rai & Kalluraya (2006 ▶); Rai et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H15N3O4

M = 373.36

Monoclinic,

a = 11.3859 (2) Å

b = 7.5746 (2) Å

c = 21.0008 (4) Å

β = 107.202 (1)°

V = 1730.17 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.19 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.981, T max = 0.990

22336 measured reflections

5085 independent reflections

2678 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.135

S = 1.02

5085 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.28 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047217/fj2257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047217/fj2257Isup2.hkl

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

C21H15N3O4	F(000) = 776
Mr = 373.36	Dx = 1.433 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2474 reflections
a = 11.3859 (2) Å	θ = 3.3–30.1°
b = 7.5746 (2) Å	µ = 0.10 mm−1
c = 21.0008 (4) Å	T = 100 K
β = 107.202 (1)°	Block, brown
V = 1730.17 (6) Å3	0.19 × 0.18 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5085 independent reflections
Radiation source: fine-focus sealed tube	2678 reflections with I > 2σ(I)
graphite	Rint = 0.085
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→16
Tmin = 0.981, Tmax = 0.990	k = −10→9
22336 measured reflections	l = −29→29

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0519P)2 + 0.0761P] where P = (Fo2 + 2Fc2)/3
5085 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.28 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	−0.26961 (11)	0.68826 (17)	−0.02101 (6)	0.0275 (3)
O2	0.05600 (11)	0.98467 (18)	0.11675 (6)	0.0286 (3)
O3	−0.56846 (12)	0.7483 (2)	−0.01746 (8)	0.0464 (4)
O4	−0.49541 (13)	0.5852 (2)	−0.08230 (8)	0.0473 (4)
N1	0.04825 (13)	0.6498 (2)	−0.06270 (7)	0.0219 (4)
N2	−0.06690 (14)	0.6518 (2)	−0.05573 (8)	0.0245 (4)
N3	−0.48241 (15)	0.6877 (2)	−0.03543 (9)	0.0340 (4)
C1	0.33869 (18)	0.7702 (3)	0.12408 (9)	0.0284 (5)
H1A	0.3085	0.6624	0.1049	0.034*
C2	0.46370 (18)	0.7905 (3)	0.15579 (10)	0.0320 (5)
H2A	0.5160	0.6946	0.1585	0.038*
C3	0.51237 (18)	0.9510 (3)	0.18361 (10)	0.0310 (5)
C4	0.43195 (18)	1.0917 (3)	0.17911 (9)	0.0294 (5)
H4A	0.4628	1.2009	0.1965	0.035*
C5	0.30696 (18)	1.0725 (3)	0.14930 (9)	0.0269 (5)
H5A	0.2546	1.1675	0.1480	0.032*
C6	0.25869 (17)	0.9108 (3)	0.12104 (9)	0.0248 (4)
C7	0.12233 (17)	0.8988 (2)	0.09159 (9)	0.0222 (4)
C8	0.06949 (16)	0.7914 (2)	0.03174 (9)	0.0222 (4)
C9	−0.05508 (16)	0.7393 (2)	0.00105 (9)	0.0220 (4)
C10	−0.16698 (17)	0.7701 (2)	0.01993 (9)	0.0236 (4)
C11	−0.19765 (17)	0.8688 (3)	0.06673 (10)	0.0281 (5)
H11A	−0.1443	0.9338	0.1007	0.034*
C12	−0.32650 (18)	0.8533 (3)	0.05368 (10)	0.0327 (5)
H12A	−0.3752	0.9068	0.0767	0.039*
C13	−0.36327 (17)	0.7451 (3)	0.00098 (10)	0.0274 (5)
C14	0.13067 (17)	0.7302 (2)	−0.01160 (9)	0.0220 (4)
H14A	0.2143	0.7425	−0.0064	0.026*
C15	0.06792 (17)	0.5688 (2)	−0.12035 (9)	0.0232 (4)
C16	−0.02628 (18)	0.4746 (3)	−0.16354 (9)	0.0273 (5)
H16A	−0.1025	0.4664	−0.1559	0.033*
C17	−0.00643 (19)	0.3924 (3)	−0.21841 (10)	0.0331 (5)
H17A	−0.0693	0.3275	−0.2473	0.040*
C18	0.10610 (19)	0.4062 (3)	−0.23042 (10)	0.0345 (5)
H18A	0.1190	0.3516	−0.2674	0.041*
C19	0.19937 (19)	0.5017 (3)	−0.18716 (10)	0.0328 (5)
H19A	0.2751	0.5111	−0.1953	0.039*
C20	0.18140 (18)	0.5839 (3)	−0.13170 (10)	0.0278 (5)
H20A	0.2445	0.6481	−0.1026	0.033*
C21	0.64761 (18)	0.9736 (3)	0.21836 (11)	0.0425 (6)
H21A	0.6768	1.0784	0.2022	0.064*
H21B	0.6916	0.8729	0.2095	0.064*
H21C	0.6607	0.9838	0.2655	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.0179 (7)	0.0278 (8)	0.0350 (8)	−0.0026 (6)	0.0053 (6)	0.0027 (6)
O2	0.0245 (8)	0.0303 (8)	0.0307 (7)	−0.0007 (6)	0.0078 (6)	−0.0007 (6)
O3	0.0191 (8)	0.0648 (12)	0.0557 (10)	−0.0010 (8)	0.0118 (8)	−0.0040 (9)
O4	0.0270 (9)	0.0471 (10)	0.0633 (11)	−0.0079 (8)	0.0062 (8)	−0.0162 (9)
N1	0.0163 (8)	0.0217 (9)	0.0264 (8)	−0.0011 (7)	0.0045 (7)	0.0028 (7)
N2	0.0185 (9)	0.0234 (9)	0.0315 (9)	0.0000 (7)	0.0073 (7)	0.0040 (7)
N3	0.0214 (10)	0.0361 (11)	0.0429 (11)	−0.0028 (8)	0.0069 (9)	0.0053 (9)
C1	0.0259 (11)	0.0278 (12)	0.0283 (11)	−0.0008 (10)	0.0031 (9)	0.0010 (9)
C2	0.0228 (11)	0.0345 (13)	0.0354 (12)	0.0051 (10)	0.0035 (10)	0.0009 (10)
C3	0.0213 (11)	0.0412 (14)	0.0279 (11)	−0.0021 (10)	0.0036 (9)	−0.0005 (10)
C4	0.0262 (11)	0.0302 (12)	0.0292 (11)	−0.0049 (10)	0.0040 (9)	−0.0017 (9)
C5	0.0244 (11)	0.0279 (12)	0.0279 (10)	0.0009 (9)	0.0070 (9)	0.0018 (9)
C6	0.0205 (10)	0.0289 (11)	0.0242 (10)	−0.0020 (9)	0.0052 (9)	0.0042 (9)
C7	0.0202 (10)	0.0216 (11)	0.0237 (10)	−0.0023 (8)	0.0046 (8)	0.0055 (8)
C8	0.0180 (10)	0.0207 (10)	0.0259 (10)	−0.0008 (8)	0.0033 (8)	0.0051 (8)
C9	0.0192 (10)	0.0184 (10)	0.0260 (10)	0.0010 (8)	0.0031 (8)	0.0058 (8)
C10	0.0187 (10)	0.0206 (11)	0.0283 (10)	−0.0031 (8)	0.0021 (9)	0.0059 (8)
C11	0.0205 (11)	0.0307 (12)	0.0321 (11)	−0.0018 (9)	0.0062 (9)	0.0013 (9)
C12	0.0242 (11)	0.0372 (13)	0.0386 (12)	−0.0002 (10)	0.0124 (10)	0.0007 (10)
C13	0.0149 (10)	0.0299 (12)	0.0363 (11)	−0.0010 (9)	0.0059 (9)	0.0066 (10)
C14	0.0164 (10)	0.0212 (11)	0.0251 (10)	−0.0016 (8)	0.0013 (8)	0.0052 (8)
C15	0.0229 (10)	0.0205 (10)	0.0240 (10)	0.0020 (9)	0.0034 (9)	0.0060 (8)
C16	0.0209 (11)	0.0295 (12)	0.0281 (10)	−0.0006 (9)	0.0020 (9)	0.0042 (9)
C17	0.0316 (13)	0.0349 (13)	0.0267 (11)	−0.0021 (10)	−0.0006 (10)	0.0000 (10)
C18	0.0383 (13)	0.0374 (13)	0.0269 (11)	0.0072 (11)	0.0083 (10)	0.0007 (10)
C19	0.0296 (12)	0.0347 (13)	0.0365 (12)	0.0051 (10)	0.0136 (10)	0.0067 (10)
C20	0.0217 (11)	0.0275 (11)	0.0319 (11)	−0.0009 (9)	0.0042 (9)	0.0030 (9)
C21	0.0238 (12)	0.0503 (16)	0.0482 (14)	−0.0021 (11)	0.0024 (11)	−0.0084 (12)

O1—C13	1.352 (2)	C8—C14	1.380 (2)
O1—C10	1.377 (2)	C8—C9	1.429 (2)
O2—C7	1.229 (2)	C9—C10	1.461 (2)
O3—N3	1.2377 (19)	C10—C11	1.360 (3)
O4—N3	1.228 (2)	C11—C12	1.415 (3)
N1—C14	1.345 (2)	C11—H11A	0.9300
N1—N2	1.3617 (19)	C12—C13	1.341 (3)
N1—C15	1.433 (2)	C12—H12A	0.9300
N2—C9	1.336 (2)	C14—H14A	0.9300
N3—C13	1.414 (2)	C15—C16	1.381 (3)
C1—C2	1.390 (3)	C15—C20	1.386 (2)
C1—C6	1.391 (3)	C16—C17	1.386 (3)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.391 (3)	C17—C18	1.381 (3)
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.390 (3)	C18—C19	1.380 (3)
C3—C21	1.506 (3)	C18—H18A	0.9300
C4—C5	1.383 (3)	C19—C20	1.388 (3)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.400 (3)	C20—H20A	0.9300
C5—H5A	0.9300	C21—H21A	0.9600
C6—C7	1.494 (3)	C21—H21B	0.9600
C7—C8	1.468 (3)	C21—H21C	0.9600
C13—O1—C10	104.64 (15)	O1—C10—C9	113.95 (16)
C14—N1—N2	112.07 (14)	C10—C11—C12	106.71 (18)
C14—N1—C15	128.45 (15)	C10—C11—H11A	126.6
N2—N1—C15	119.47 (15)	C12—C11—H11A	126.6
C9—N2—N1	104.81 (15)	C13—C12—C11	105.26 (17)
O4—N3—O3	124.09 (18)	C13—C12—H12A	127.4
O4—N3—C13	119.78 (17)	C11—C12—H12A	127.4
O3—N3—C13	116.12 (18)	C12—C13—O1	113.05 (17)
C2—C1—C6	120.08 (19)	C12—C13—N3	130.51 (18)
C2—C1—H1A	120.0	O1—C13—N3	116.41 (18)
C6—C1—H1A	120.0	N1—C14—C8	108.03 (16)
C1—C2—C3	121.47 (19)	N1—C14—H14A	126.0
C1—C2—H2A	119.3	C8—C14—H14A	126.0
C3—C2—H2A	119.3	C16—C15—C20	120.81 (18)
C4—C3—C2	117.98 (19)	C16—C15—N1	119.41 (16)
C4—C3—C21	120.30 (19)	C20—C15—N1	119.78 (17)
C2—C3—C21	121.72 (19)	C15—C16—C17	119.49 (17)
C5—C4—C3	121.27 (19)	C15—C16—H16A	120.3
C5—C4—H4A	119.4	C17—C16—H16A	120.3
C3—C4—H4A	119.4	C18—C17—C16	120.4 (2)
C4—C5—C6	120.43 (18)	C18—C17—H17A	119.8
C4—C5—H5A	119.8	C16—C17—H17A	119.8
C6—C5—H5A	119.8	C19—C18—C17	119.62 (19)
C1—C6—C5	118.74 (18)	C19—C18—H18A	120.2
C1—C6—C7	123.94 (18)	C17—C18—H18A	120.2
C5—C6—C7	117.27 (17)	C18—C19—C20	120.77 (18)
O2—C7—C8	120.88 (17)	C18—C19—H19A	119.6
O2—C7—C6	119.03 (17)	C20—C19—H19A	119.6
C8—C7—C6	120.04 (16)	C15—C20—C19	118.91 (19)
C14—C8—C9	103.72 (16)	C15—C20—H20A	120.5
C14—C8—C7	126.29 (17)	C19—C20—H20A	120.5
C9—C8—C7	129.78 (16)	C3—C21—H21A	109.5
N2—C9—C8	111.36 (15)	C3—C21—H21B	109.5
N2—C9—C10	117.12 (17)	H21A—C21—H21B	109.5
C8—C9—C10	131.49 (18)	C3—C21—H21C	109.5
C11—C10—O1	110.30 (15)	H21A—C21—H21C	109.5
C11—C10—C9	135.64 (18)	H21B—C21—H21C	109.5
C14—N1—N2—C9	1.1 (2)	N2—C9—C10—O1	6.0 (2)
C15—N1—N2—C9	−178.35 (15)	C8—C9—C10—O1	−176.27 (17)
C6—C1—C2—C3	−1.6 (3)	O1—C10—C11—C12	−1.9 (2)
C1—C2—C3—C4	0.3 (3)	C9—C10—C11—C12	174.0 (2)
C1—C2—C3—C21	179.66 (18)	C10—C11—C12—C13	0.9 (2)
C2—C3—C4—C5	1.4 (3)	C11—C12—C13—O1	0.4 (2)
C21—C3—C4—C5	−177.92 (17)	C11—C12—C13—N3	−177.31 (19)
C3—C4—C5—C6	−1.9 (3)	C10—O1—C13—C12	−1.5 (2)
C2—C1—C6—C5	1.2 (3)	C10—O1—C13—N3	176.56 (16)
C2—C1—C6—C7	−176.31 (17)	O4—N3—C13—C12	−179.2 (2)
C4—C5—C6—C1	0.5 (3)	O3—N3—C13—C12	1.7 (3)
C4—C5—C6—C7	178.19 (16)	O4—N3—C13—O1	3.2 (3)
C1—C6—C7—O2	144.79 (18)	O3—N3—C13—O1	−175.94 (16)
C5—C6—C7—O2	−32.7 (2)	N2—N1—C14—C8	−0.6 (2)
C1—C6—C7—C8	−37.8 (3)	C15—N1—C14—C8	178.73 (16)
C5—C6—C7—C8	144.68 (17)	C9—C8—C14—N1	−0.1 (2)
O2—C7—C8—C14	160.61 (18)	C7—C8—C14—N1	−175.08 (17)
C6—C7—C8—C14	−16.7 (3)	C14—N1—C15—C16	172.41 (18)
O2—C7—C8—C9	−13.1 (3)	N2—N1—C15—C16	−8.3 (3)
C6—C7—C8—C9	169.56 (18)	C14—N1—C15—C20	−6.8 (3)
N1—N2—C9—C8	−1.1 (2)	N2—N1—C15—C20	172.55 (16)
N1—N2—C9—C10	177.03 (15)	C20—C15—C16—C17	0.8 (3)
C14—C8—C9—N2	0.8 (2)	N1—C15—C16—C17	−178.34 (17)
C7—C8—C9—N2	175.53 (17)	C15—C16—C17—C18	−0.9 (3)
C14—C8—C9—C10	−177.03 (19)	C16—C17—C18—C19	0.4 (3)
C7—C8—C9—C10	−2.3 (3)	C17—C18—C19—C20	0.0 (3)
C13—O1—C10—C11	2.0 (2)	C16—C15—C20—C19	−0.4 (3)
C13—O1—C10—C9	−174.79 (15)	N1—C15—C20—C19	178.79 (17)
N2—C9—C10—C11	−169.7 (2)	C18—C19—C20—C15	−0.1 (3)
C8—C9—C10—C11	8.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2	0.93	2.24	2.902 (2)	128
C14—H14A···O3i	0.93	2.55	3.467 (2)	168
C20—H20A···O3i	0.93	2.46	3.373 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2	0.93	2.24	2.902 (2)	128
C14—H14A⋯O3i	0.93	2.55	3.467 (2)	168
C20—H20A⋯O3i	0.93	2.46	3.373 (3)	166

Symmetry code: (i) .