1-Cyclo-pentyl-idene-2-(2,4-dinitro-phenyl)-hydrazine.

The title compound, C(11)H(12)N(4)O(4), was synthesized by the reaction of (2,4-dinitro-phen-yl)hydrazine with cyclo-penta-none. The cyclo-pentyl fragment is disordered over two sites with occupancies of 0.63 (1) and 0.37 (1). An intra-molecular N-H⋯O hydrogen bond helps to establish the conformation. Pairs of mol-ecules are held together by π-π inter-actions between adjacent benzene rings [centroid-to-centroid distance 3.589 (2) Å].

Related literature

For background literature on Schiff bases, see: Liang (2007 ▶). For information on the properties of dinitro­phenyl­hydrazones, see: Baughman et al. (2004 ▶); Zare et al. (2005 ▶); El-Seify & El-Dossoki (2006 ▶); Kim & Yoon (1998 ▶). For bond-length data, see: Allen et al. (1987 ▶); Allen (2002 ▶).

Experimental

Crystal data

C11H12N4O4

M = 264.25

Monoclinic,

a = 6.962 (3) Å

b = 21.840 (10) Å

c = 8.162 (4) Å

β = 98.528 (9)°

V = 1227.3 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 (2) K

0.15 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.993

6423 measured reflections

2168 independent reflections

1353 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.129

S = 1.02

2168 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033345/fb2114sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033345/fb2114Isup2.hkl

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

C11H12N4O4	F(000) = 552
Mr = 264.25	Dx = 1.430 Mg m−3
Monoclinic, P21/n	Melting point = 318–320 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.962 (3) Å	Cell parameters from 1213 reflections
b = 21.84 (1) Å	θ = 3.1–21.3°
c = 8.162 (4) Å	µ = 0.11 mm−1
β = 98.528 (9)°	T = 295 K
V = 1227.3 (10) Å3	Block, brown
Z = 4	0.15 × 0.10 × 0.06 mm

Bruker SMART CCD diffractometer	2168 independent reflections
Radiation source: fine-focus sealed tube	1353 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.984, Tmax = 0.993	k = −20→26
6423 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.1369P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2168 reflections	Δρmax = 0.13 e Å−3
192 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
64 constraints	Extinction coefficient: 0.008 (2)
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
O1	0.7332 (3)	−0.13258 (8)	0.3023 (2)	0.0970 (6)
O2	0.6598 (2)	−0.04170 (8)	0.3749 (2)	0.0883 (6)
O3	1.2739 (3)	−0.17276 (10)	0.0323 (3)	0.1106 (7)
O4	1.4641 (3)	−0.09968 (8)	−0.0180 (2)	0.0979 (6)
N1	0.7661 (3)	−0.07782 (10)	0.3142 (2)	0.0715 (5)
N2	1.3231 (3)	−0.11920 (11)	0.0400 (2)	0.0802 (6)
N3	0.8813 (2)	0.05130 (8)	0.3322 (2)	0.0643 (5)
H3	0.7731	0.0416	0.3643	0.077*
N4	0.9487 (3)	0.11105 (8)	0.3468 (2)	0.0716 (5)
C1	0.9877 (3)	0.00874 (9)	0.2673 (2)	0.0563 (5)
C2	0.9367 (3)	−0.05376 (9)	0.2535 (2)	0.0583 (5)
C3	1.0473 (3)	−0.09546 (10)	0.1801 (2)	0.0641 (6)
H3A	1.0114	−0.1365	0.1717	0.077*
C4	1.2096 (3)	−0.07577 (10)	0.1204 (2)	0.0634 (6)
C5	1.2658 (3)	−0.01508 (10)	0.1343 (3)	0.0653 (6)
H5	1.3777	−0.0024	0.0944	0.078*
C6	1.1586 (3)	0.02600 (10)	0.2058 (3)	0.0631 (6)
H6	1.1986	0.0666	0.2145	0.076*
C7	0.8305 (3)	0.15004 (10)	0.3923 (3)	0.0690 (6)
C8	0.6290 (3)	0.14145 (10)	0.4287 (3)	0.0785 (7)
H8A	0.6292	0.1186	0.5306	0.094*
H8B	0.5503	0.1197	0.3391	0.094*
C9	0.5515 (8)	0.2067 (3)	0.4458 (10)	0.0954 (16)	0.631 (10)
H9A	0.4572	0.2078	0.5221	0.114*	0.631 (10)
H9B	0.4921	0.2227	0.3393	0.114*	0.631 (10)
C10	0.7337 (8)	0.2425 (3)	0.5134 (10)	0.0972 (15)	0.631 (10)
H10A	0.7157	0.2860	0.4924	0.117*	0.631 (10)
H10B	0.7690	0.2360	0.6316	0.117*	0.631 (10)
C10'	0.7036 (14)	0.2469 (4)	0.4218 (16)	0.090 (2)	0.369 (10)
H10C	0.6345	0.2536	0.3111	0.108*	0.369 (10)
H10D	0.7224	0.2859	0.4788	0.108*	0.369 (10)
C9'	0.5961 (19)	0.2020 (4)	0.5176 (14)	0.087 (2)	0.369 (10)
H9'1	0.4591	0.2119	0.5080	0.105*	0.369 (10)
H9'2	0.6518	0.2006	0.6337	0.105*	0.369 (10)
C11	0.8888 (4)	0.21600 (11)	0.4170 (4)	0.0979 (8)
H11A	0.8868	0.2367	0.3116	0.117*
H11B	1.0176	0.2196	0.4805	0.117*

	U11	U22	U33	U12	U13	U23
O1	0.0998 (14)	0.0748 (12)	0.1191 (15)	−0.0291 (10)	0.0247 (11)	0.0028 (10)
O2	0.0678 (11)	0.0882 (12)	0.1131 (14)	−0.0079 (9)	0.0276 (10)	0.0071 (10)
O3	0.1313 (17)	0.0738 (12)	0.1310 (17)	0.0164 (11)	0.0340 (13)	−0.0039 (11)
O4	0.0988 (14)	0.1102 (14)	0.0911 (13)	0.0162 (11)	0.0353 (11)	0.0015 (11)
N1	0.0660 (13)	0.0744 (14)	0.0725 (13)	−0.0132 (11)	0.0047 (10)	0.0104 (10)
N2	0.0869 (15)	0.0837 (16)	0.0694 (13)	0.0160 (13)	0.0095 (11)	0.0062 (11)
N3	0.0584 (11)	0.0658 (11)	0.0695 (12)	−0.0059 (9)	0.0124 (9)	0.0045 (9)
N4	0.0675 (12)	0.0604 (11)	0.0879 (14)	−0.0060 (10)	0.0151 (10)	0.0050 (10)
C1	0.0544 (12)	0.0634 (12)	0.0494 (11)	−0.0002 (10)	0.0019 (9)	0.0087 (9)
C2	0.0562 (12)	0.0630 (12)	0.0535 (11)	−0.0059 (10)	0.0011 (9)	0.0108 (10)
C3	0.0697 (14)	0.0613 (13)	0.0575 (12)	−0.0040 (11)	−0.0025 (11)	0.0099 (10)
C4	0.0685 (14)	0.0646 (13)	0.0555 (12)	0.0088 (11)	0.0032 (10)	0.0091 (10)
C5	0.0593 (12)	0.0761 (14)	0.0610 (13)	−0.0003 (11)	0.0104 (10)	0.0106 (11)
C6	0.0625 (13)	0.0638 (13)	0.0626 (13)	−0.0067 (10)	0.0080 (11)	0.0077 (10)
C7	0.0733 (14)	0.0660 (13)	0.0688 (14)	−0.0015 (12)	0.0145 (11)	0.0070 (11)
C8	0.0805 (16)	0.0807 (15)	0.0784 (15)	−0.0003 (12)	0.0254 (12)	0.0018 (12)
C9	0.104 (3)	0.095 (3)	0.093 (3)	0.023 (2)	0.030 (3)	0.011 (3)
C10	0.118 (3)	0.076 (3)	0.098 (3)	0.011 (2)	0.016 (3)	0.002 (3)
C10'	0.110 (4)	0.066 (3)	0.094 (4)	0.012 (3)	0.016 (4)	0.007 (4)
C9'	0.095 (4)	0.080 (3)	0.090 (4)	0.010 (3)	0.026 (4)	0.007 (4)
C11	0.1034 (19)	0.0699 (15)	0.123 (2)	−0.0041 (14)	0.0257 (16)	0.0030 (14)

O1—N1	1.219 (2)	C7—C11	1.502 (3)
O2—N1	1.234 (2)	C8—C9	1.538 (6)
O3—N2	1.218 (2)	C8—C9'	1.542 (10)
O4—N2	1.227 (3)	C8—H8A	0.9700
N1—C2	1.452 (3)	C8—H8B	0.9700
N2—C4	1.453 (3)	C9—C10	1.522 (7)
N3—C1	1.345 (3)	C9—H9A	0.9700
N3—N4	1.386 (2)	C9—H9B	0.9700
N3—H3	0.8600	C10—C11	1.540 (6)
N4—C7	1.277 (3)	C10—H10A	0.9700
C1—C6	1.409 (3)	C10—H10B	0.9700
C1—C2	1.411 (3)	C10'—C11	1.461 (9)
C2—C3	1.385 (3)	C10'—C9'	1.519 (2)
C3—C4	1.364 (3)	C10'—H10C	0.9700
C3—H3A	0.9300	C10'—H10D	0.9700
C4—C5	1.382 (3)	C9'—H9'1	0.9700
C5—C6	1.354 (3)	C9'—H9'2	0.9700
C5—H5	0.9300	C11—H11A	0.9700
C6—H6	0.9300	C11—H11B	0.9700
C7—C8	1.488 (3)
O1—N1—O2	122.8 (2)	C9—C8—H8B	110.8
O1—N1—C2	118.8 (2)	C9'—C8—H8B	131.9
O2—N1—C2	118.38 (19)	H8A—C8—H8B	108.9
O3—N2—O4	123.3 (2)	C8—C9—C10	102.9 (5)
O3—N2—C4	118.9 (2)	C8—C9—H9A	111.2
O4—N2—C4	117.9 (2)	C10—C9—H9A	111.2
C1—N3—N4	119.05 (18)	C8—C9—H9B	111.2
C1—N3—H3	120.5	C10—C9—H9B	111.2
N4—N3—H3	120.5	H9A—C9—H9B	109.1
C7—N4—N3	115.38 (19)	C11—C10—C9	103.4 (5)
N3—C1—C6	119.90 (19)	C11—C10—H10A	111.1
N3—C1—C2	123.60 (19)	C9—C10—H10A	111.1
C6—C1—C2	116.5 (2)	C11—C10—H10B	111.1
C3—C2—C1	121.43 (19)	C9—C10—H10B	111.1
C3—C2—N1	116.4 (2)	H10A—C10—H10B	109.0
C1—C2—N1	122.1 (2)	C11—C10'—C9'	102.7 (7)
C4—C3—C2	119.3 (2)	C11—C10'—H10C	111.2
C4—C3—H3A	120.3	C9'—C10'—H10C	111.2
C2—C3—H3A	120.3	C11—C10'—H10D	111.2
C3—C4—C5	120.8 (2)	C9'—C10'—H10D	111.2
C3—C4—N2	119.4 (2)	H10C—C10'—H10D	109.1
C5—C4—N2	119.8 (2)	C10'—C9'—C8	101.1 (7)
C6—C5—C4	120.2 (2)	C10'—C9'—H9'1	111.5
C6—C5—H5	119.9	C8—C9'—H9'1	111.5
C4—C5—H5	119.9	C10'—C9'—H9'2	111.5
C5—C6—C1	121.7 (2)	C8—C9'—H9'2	111.5
C5—C6—H6	119.2	H9'1—C9'—H9'2	109.4
C1—C6—H6	119.2	C10'—C11—C7	103.0 (4)
N4—C7—C8	129.9 (2)	C7—C11—C10	103.5 (3)
N4—C7—C11	120.4 (2)	C10'—C11—H11A	85.0
C8—C7—C11	109.8 (2)	C7—C11—H11A	111.1
C7—C8—C9	104.8 (3)	C10—C11—H11A	111.1
C7—C8—C9'	101.3 (4)	C10'—C11—H11B	134.2
C7—C8—H8A	110.8	C7—C11—H11B	111.1
C9—C8—H8A	110.8	C10—C11—H11B	111.1
C9'—C8—H8A	91.1	H11A—C11—H11B	109.0
C7—C8—H8B	110.8

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2	0.86	1.99	2.605 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2	0.86	1.99	2.605 (2)	128