(E)-2-Furyl methyl ketone 2,4-dinitro-phenyl-hydrazone.

Crystals of the title compound, C(12)H(10)N(4)O(5), were obtained from a condensation reaction of 2,4-dinitro-phenyl-hydrazine and 2-furyl methyl ketone. The mol-ecule displays a nearly planar structure, and the furan ring is slightly twisted by a dihedral angle of 12.62 (6)° with respect to the phenyl-hydrazone plane. The face-to-face separation of 3.287 (7) Å between parallel benzene rings of adjacent mol-ecules indicates the existence of π-π stacking between dinitro-phenyl rings in the crystal structure.

Related literature

For general background, see: Okabe et al. (1993 ▶); Shan et al. (2003a ▶, 2006 ▶). For related structures, see: Vickery et al. (1985 ▶); Fan et al. (2004 ▶); Shan et al. (2003b ▶).

Experimental

Crystal data

C12H10N4O5

M = 290.24

Monoclinic,

a = 9.8917 (8) Å

b = 12.8477 (15) Å

c = 10.6549 (12) Å

β = 111.63 (2)°

V = 1258.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 (2) K

0.36 × 0.23 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

12121 measured reflections

2858 independent reflections

1784 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.03

2858 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015122/om2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015122/om2233Isup2.hkl

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

C12H10N4O5	F000 = 600
Mr = 290.24	Dx = 1.532 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5266 reflections
a = 9.8917 (8) Å	θ = 3.2–26.0º
b = 12.8477 (15) Å	µ = 0.12 mm−1
c = 10.6549 (12) Å	T = 293 (2) K
β = 111.63 (2)º	Prism, brown
V = 1258.7 (3) Å3	0.36 × 0.23 × 0.18 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2858 independent reflections
Radiation source: fine-focus sealed tube	1784 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 10.00 pixels mm-1	θmax = 27.4º
T = 293(2) K	θmin = 3.2º
ω scans	h = −12→12
Absorption correction: none	k = −16→16
12121 measured reflections	l = −13→13

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0649P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.21 e Å−3
2858 reflections	Δρmin = −0.17 e Å−3
192 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (11)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.13582 (13)	0.43547 (8)	0.14104 (11)	0.0648 (4)
O2	0.15573 (13)	0.27996 (8)	0.22020 (12)	0.0648 (4)
O3	0.44159 (13)	0.19704 (8)	0.66737 (13)	0.0660 (4)
O4	0.52296 (15)	0.31707 (10)	0.81753 (13)	0.0742 (4)
O5	0.09817 (11)	0.93990 (8)	0.18361 (12)	0.0566 (3)
N1	0.17859 (13)	0.37357 (9)	0.23615 (12)	0.0452 (3)
N2	0.45693 (14)	0.28930 (10)	0.70150 (14)	0.0498 (3)
N3	0.21841 (13)	0.59367 (8)	0.30483 (12)	0.0412 (3)
H3	0.1757	0.5753	0.2219	0.049*
N4	0.22992 (13)	0.69747 (8)	0.33900 (12)	0.0411 (3)
C1	0.27421 (13)	0.52042 (9)	0.40146 (14)	0.0349 (3)
C2	0.25858 (14)	0.41229 (10)	0.37100 (14)	0.0368 (3)
C3	0.31897 (14)	0.33809 (10)	0.46968 (15)	0.0406 (3)
H3A	0.3085	0.2677	0.4478	0.049*
C4	0.39417 (14)	0.36870 (10)	0.59975 (15)	0.0403 (3)
C5	0.40955 (15)	0.47424 (11)	0.63469 (15)	0.0412 (3)
H5	0.4597	0.4940	0.7238	0.049*
C6	0.35072 (14)	0.54818 (10)	0.53751 (14)	0.0393 (3)
H6	0.3613	0.6182	0.5615	0.047*
C7	0.16518 (14)	0.76093 (10)	0.24031 (14)	0.0395 (3)
C8	0.18273 (16)	0.87045 (10)	0.27796 (16)	0.0431 (4)
C9	0.26625 (19)	0.92158 (12)	0.38905 (18)	0.0586 (4)
H9	0.3329	0.8926	0.4674	0.070*
C10	0.2326 (2)	1.02927 (13)	0.3632 (2)	0.0691 (5)
H10	0.2734	1.0842	0.4218	0.083*
C11	0.1335 (2)	1.03623 (12)	0.2414 (2)	0.0662 (5)
H11	0.0926	1.0983	0.1997	0.079*
C12	0.07984 (19)	0.73130 (12)	0.09826 (17)	0.0556 (4)
H12A	0.1447	0.7073	0.0560	0.083*
H12B	0.0268	0.7907	0.0502	0.083*
H12C	0.0130	0.6767	0.0968	0.083*

	U11	U22	U33	U12	U13	U23
O1	0.0920 (9)	0.0420 (6)	0.0438 (7)	−0.0007 (6)	0.0055 (6)	−0.0006 (5)
O2	0.0836 (8)	0.0323 (6)	0.0615 (8)	−0.0105 (5)	0.0068 (6)	−0.0098 (5)
O3	0.0778 (8)	0.0408 (6)	0.0728 (9)	0.0058 (5)	0.0200 (7)	0.0147 (5)
O4	0.0884 (9)	0.0708 (8)	0.0459 (8)	0.0053 (7)	0.0041 (7)	0.0107 (6)
O5	0.0572 (6)	0.0371 (6)	0.0754 (8)	0.0069 (5)	0.0242 (6)	0.0136 (5)
N1	0.0513 (7)	0.0333 (6)	0.0443 (8)	−0.0020 (5)	0.0096 (6)	−0.0035 (5)
N2	0.0510 (7)	0.0468 (8)	0.0489 (9)	0.0030 (6)	0.0151 (6)	0.0111 (6)
N3	0.0510 (7)	0.0272 (5)	0.0399 (7)	−0.0003 (5)	0.0103 (5)	−0.0014 (5)
N4	0.0490 (7)	0.0263 (6)	0.0468 (7)	−0.0013 (5)	0.0164 (6)	−0.0013 (5)
C1	0.0349 (7)	0.0296 (6)	0.0404 (8)	−0.0010 (5)	0.0142 (6)	−0.0009 (5)
C2	0.0373 (7)	0.0305 (6)	0.0400 (8)	−0.0020 (5)	0.0112 (6)	−0.0026 (5)
C3	0.0411 (7)	0.0297 (6)	0.0492 (9)	−0.0020 (5)	0.0147 (7)	0.0013 (6)
C4	0.0395 (7)	0.0372 (7)	0.0434 (9)	0.0017 (6)	0.0146 (6)	0.0064 (6)
C5	0.0421 (7)	0.0439 (8)	0.0366 (8)	−0.0028 (6)	0.0132 (6)	−0.0034 (6)
C6	0.0433 (7)	0.0316 (7)	0.0448 (9)	−0.0023 (6)	0.0181 (6)	−0.0047 (6)
C7	0.0428 (7)	0.0343 (7)	0.0427 (8)	−0.0003 (6)	0.0171 (6)	0.0024 (6)
C8	0.0507 (8)	0.0319 (7)	0.0496 (9)	0.0045 (6)	0.0220 (7)	0.0084 (6)
C9	0.0800 (11)	0.0390 (8)	0.0549 (10)	−0.0056 (8)	0.0227 (9)	−0.0049 (7)
C10	0.0959 (14)	0.0354 (8)	0.0892 (15)	−0.0106 (8)	0.0495 (13)	−0.0130 (9)
C11	0.0762 (12)	0.0289 (8)	0.1072 (18)	0.0051 (8)	0.0499 (13)	0.0085 (9)
C12	0.0682 (10)	0.0446 (8)	0.0471 (10)	0.0010 (8)	0.0133 (8)	0.0036 (7)

O1—N1	1.2338 (16)	C3—H3A	0.9300
O2—N1	1.2239 (15)	C4—C5	1.3995 (19)
O3—N2	1.2327 (17)	C5—C6	1.367 (2)
O4—N2	1.2194 (18)	C5—H5	0.9300
O5—C11	1.369 (2)	C6—H6	0.9300
O5—C8	1.3735 (18)	C7—C8	1.4560 (19)
N1—C2	1.4491 (18)	C7—C12	1.485 (2)
N2—C4	1.4510 (18)	C8—C9	1.339 (2)
N3—C1	1.3533 (17)	C9—C10	1.426 (2)
N3—N4	1.3760 (15)	C9—H9	0.9300
N3—H3	0.8600	C10—C11	1.309 (3)
N4—C7	1.2977 (18)	C10—H10	0.9300
C1—C6	1.4115 (19)	C11—H11	0.9300
C1—C2	1.4221 (17)	C12—H12A	0.9600
C2—C3	1.3813 (19)	C12—H12B	0.9600
C3—C4	1.367 (2)	C12—H12C	0.9600
C11—O5—C8	105.81 (13)	C4—C5—H5	120.1
O2—N1—O1	121.97 (13)	C5—C6—C1	121.31 (13)
O2—N1—C2	118.71 (12)	C5—C6—H6	119.3
O1—N1—C2	119.32 (11)	C1—C6—H6	119.3
O4—N2—O3	122.83 (14)	N4—C7—C8	114.26 (13)
O4—N2—C4	118.26 (13)	N4—C7—C12	126.16 (13)
O3—N2—C4	118.91 (14)	C8—C7—C12	119.58 (12)
C1—N3—N4	120.13 (12)	C9—C8—O5	109.82 (13)
C1—N3—H3	119.9	C9—C8—C7	133.59 (14)
N4—N3—H3	119.9	O5—C8—C7	116.59 (13)
C7—N4—N3	115.25 (12)	C8—C9—C10	106.32 (17)
N3—C1—C6	121.30 (12)	C8—C9—H9	126.8
N3—C1—C2	121.75 (13)	C10—C9—H9	126.8
C6—C1—C2	116.95 (12)	C11—C10—C9	107.09 (16)
C3—C2—C1	121.36 (13)	C11—C10—H10	126.5
C3—C2—N1	116.28 (12)	C9—C10—H10	126.5
C1—C2—N1	122.37 (12)	C10—C11—O5	110.96 (14)
C4—C3—C2	119.62 (13)	C10—C11—H11	124.5
C4—C3—H3A	120.2	O5—C11—H11	124.5
C2—C3—H3A	120.2	C7—C12—H12A	109.5
C3—C4—C5	120.90 (13)	C7—C12—H12B	109.5
C3—C4—N2	118.57 (13)	H12A—C12—H12B	109.5
C5—C4—N2	120.52 (13)	C7—C12—H12C	109.5
C6—C5—C4	119.84 (13)	H12A—C12—H12C	109.5
C6—C5—H5	120.1	H12B—C12—H12C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	1.97	2.6063 (15)	130
C9—H9···O4i	0.93	2.41	3.334 (2)	172
C11—H11···O2ii	0.93	2.41	3.1530 (19)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.86	1.97	2.6063 (15)	130
C9—H9⋯O4i	0.93	2.41	3.334 (2)	172
C11—H11⋯O2ii	0.93	2.41	3.1530 (19)	137

Symmetry codes: (i) ; (ii) .