N-Cyclo­heptyl­idene-N′-(2,4-dinitro­phenyl)hydrazine

Kia, R.; Fun, H.-K.; Kargar, H.

doi:10.1107/S1600536809002657

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o382

doi:10.1107/S1600536809002657

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N-Cycloheptylidene-N′-(2,4-dinitrophenyl)hydrazine

Reza Kia,^a Hoong-Kun Fun ^a ^* and Hadi Kargar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 10 January 2009; accepted 21 January 2009; online 23 January 2009)

The title compound, C₁₃H₁₆N₄O₄, is a new hydrazone. An intramolecular N—H⋯O hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The nitro groups in the ortho and para positions are almost coplanar with the benzene ring to which they are bound, making dihedral angles of 0.60 (11) and 3.18 (11)°, respectively. Pairs of intermolecular C—H⋯O hydrogen bonds link neighbouring molecules into inversion dimers with R₂²(10) motifs. The crystal structure is further stabilized by intermolecular π–π interactions, with a benzene centroid-to-centroid distance of 3.6601 (4) Å.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related literature on the applications of hydrazone, see, for example: Niknam et al., (2005 ); Guillaumont & Nakamura (2000 ); Raj & Kurup (2006 ); Okabe et al. (1993 ).

Experimental

Crystal data

C₁₃H₁₆N₄O₄
M_r = 292.30
Monoclinic, P 2₁ /n
a = 6.9721 (1) Å
b = 23.7359 (5) Å
c = 8.2274 (2) Å
β = 102.351 (1)°
V = 1330.03 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100.0 (1) K
0.51 × 0.45 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.946, T_max = 0.991
26146 measured reflections
5824 independent reflections
4916 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.113
S = 1.04
5824 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2	0.888 (14)	1.947 (14)	2.6225 (9)	131.7 (12)
C2—H2A⋯O3ⁱ	0.95	2.52	3.3165 (10)	142
Symmetry code: (i) -x, -y, -z+1.

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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002657/kj2114sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002657/kj2114Isup2.hkl

checkCIF report

Comment top

2,4-Dinitrophenylhydrazones play an important role as stabilizers for the detection and protection of the carbonyl group (Niknam et al., 2005). 2,4-Dinitrophenylhydrazone derivatives are widely used in as dyes (Guillaumont & Nakamura, 2000). They are also found to have versatile coordinating abilities towards different metal ions (Raj & Kurup, 2006). In addition, some phenylhydrazone derivatives have been shown to be potentially DNA-damaging and mutagenic agents (Okabe et al., 1993).

The title compound (Fig. 1) is a new hydrazone. An intramolecular N—H···O hydrogen bond generates a six-membered ring, producing an S(6) ring motif (Bernstein et al., 1995). The nitro groups in the ortho and para positions are almost coplanar with the benzene ring to which they are bound, making dihedral angles of 0.60 (11)° and 3.18 (11)°, respectively. The cycloheptanone ring is puckered with a total puckering amplitude, Q = 0.7820 (8) Å. Pairs of intermolecular C—H···O hydrogen bonds link neighbouring molecules into dimers with R₂²(10) motifs (Table 1, Fig. 2). The crystal structure is further stabilized by intermolecular π–π interactions [Cg1···Cg1(1 - x, -y, 1 - z) = 3.6601 (4) Å, with Cg the centroid of the benzene ring].

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For related literature on the applications of hydrazone, see, for example: Niknam et al., (2005); Guillaumont & Nakamura (2000); Raj & Kurup (2006); Okabe et al. (1993).

Experimental top

The title compound was synthesized based on the reported procedure (Okabe et al. 1993). Single crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a saturated solution of the resulted compound in DMF.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. View of the molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms. Intramolecular hydrogen bond is shown as dash lines.
	Fig. 2. The crystal packing of the title compound, viewed down the c-axis showing dimer formation. Intermolecular hydrogen bonds are shown as dashed lines.

N-Cycloheptylidene-N'-(2,4-dinitrophenyl)hydrazine top

Crystal data top

C₁₃H₁₆N₄O₄	F(000) = 616
M_r = 292.30	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9967 reflections
a = 6.9721 (1) Å	θ = 2.7–40.2°
b = 23.7359 (5) Å	µ = 0.11 mm⁻¹
c = 8.2274 (2) Å	T = 100 K
β = 102.351 (1)°	Plate, yellow
V = 1330.03 (5) Å³	0.51 × 0.45 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5824 independent reflections
Radiation source: fine-focus sealed tube	4916 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 35.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.946, T_max = 0.991	k = −38→38
26146 measured reflections	l = −12→13

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0637P)² + 0.2167P] where P = (F_o² + 2F_c²)/3
5824 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₃H₁₆N₄O₄	V = 1330.03 (5) Å³
M_r = 292.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.9721 (1) Å	µ = 0.11 mm⁻¹
b = 23.7359 (5) Å	T = 100 K
c = 8.2274 (2) Å	0.51 × 0.45 × 0.08 mm
β = 102.351 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5824 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4916 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.991	R_int = 0.026
26146 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.43 e Å⁻³
5824 reflections	Δρ_min = −0.30 e Å⁻³
194 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cryosystem Cobra low-temperature attachment.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.71910 (9)	−0.13041 (2)	0.17783 (8)	0.02285 (12)
O2	0.81378 (8)	−0.04726 (2)	0.11828 (8)	0.02030 (12)
O3	0.01157 (8)	−0.08982 (3)	0.49098 (7)	0.02059 (12)
O4	0.17434 (9)	−0.16037 (2)	0.41905 (8)	0.02340 (13)
N1	0.62623 (9)	0.04321 (3)	0.18111 (8)	0.01434 (11)
N2	0.58494 (9)	0.10007 (2)	0.19219 (8)	0.01495 (11)
N3	0.70085 (9)	−0.07900 (3)	0.17430 (8)	0.01533 (11)
N4	0.14350 (9)	−0.10960 (3)	0.42854 (8)	0.01614 (12)
C1	0.34898 (10)	0.02454 (3)	0.30373 (9)	0.01400 (12)
H1A	0.3228	0.0638	0.3054	0.017*
C2	0.23044 (10)	−0.01240 (3)	0.36477 (9)	0.01428 (12)
H2A	0.1231	0.0012	0.4077	0.017*
C3	0.26847 (10)	−0.07040 (3)	0.36355 (8)	0.01365 (12)
C4	0.42249 (10)	−0.09135 (3)	0.30138 (8)	0.01385 (12)
H4A	0.4470	−0.1307	0.3017	0.017*
C5	0.54189 (9)	−0.05386 (3)	0.23798 (8)	0.01284 (11)
C6	0.51047 (9)	0.00541 (3)	0.23793 (8)	0.01249 (11)
C7	0.71332 (10)	0.13537 (3)	0.16026 (9)	0.01369 (12)
C8	0.90306 (10)	0.11873 (3)	0.11327 (9)	0.01459 (12)
H8A	0.8734	0.1078	−0.0056	0.018*
H8B	0.9549	0.0849	0.1784	0.018*
C9	1.06529 (10)	0.16349 (3)	0.13962 (9)	0.01612 (13)
H9A	1.0778	0.1796	0.2524	0.019*
H9B	1.1911	0.1447	0.1362	0.019*
C10	1.03488 (12)	0.21200 (3)	0.01374 (11)	0.02085 (15)
H10A	1.1629	0.2307	0.0187	0.025*
H10B	0.9920	0.1959	−0.0993	0.025*
C11	0.88606 (11)	0.25661 (3)	0.03869 (10)	0.01808 (13)
H11A	0.9336	0.2747	0.1483	0.022*
H11B	0.8801	0.2860	−0.0475	0.022*
C12	0.67896 (11)	0.23445 (3)	0.03073 (10)	0.01820 (14)
H12A	0.6359	0.2131	−0.0741	0.022*
H12B	0.5890	0.2669	0.0276	0.022*
C13	0.66109 (11)	0.19625 (3)	0.17764 (10)	0.01816 (13)
H13A	0.7471	0.2115	0.2797	0.022*
H13B	0.5242	0.1982	0.1930	0.022*
H1N1	0.727 (2)	0.0296 (6)	0.1432 (17)	0.036 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0256 (3)	0.0139 (2)	0.0313 (3)	0.0047 (2)	0.0112 (2)	−0.0015 (2)
O2	0.0173 (2)	0.0201 (2)	0.0264 (3)	−0.00068 (19)	0.0112 (2)	−0.0007 (2)
O3	0.0189 (2)	0.0239 (3)	0.0216 (3)	−0.0013 (2)	0.0100 (2)	0.0012 (2)
O4	0.0262 (3)	0.0139 (2)	0.0317 (3)	−0.0030 (2)	0.0096 (2)	0.0025 (2)
N1	0.0135 (2)	0.0119 (2)	0.0186 (3)	−0.00005 (18)	0.00577 (19)	0.00008 (19)
N2	0.0142 (2)	0.0117 (2)	0.0198 (3)	0.00064 (18)	0.0055 (2)	0.0012 (2)
N3	0.0145 (2)	0.0153 (3)	0.0166 (3)	0.00157 (19)	0.00412 (19)	−0.0017 (2)
N4	0.0161 (3)	0.0163 (3)	0.0162 (3)	−0.0022 (2)	0.0037 (2)	0.0015 (2)
C1	0.0132 (3)	0.0127 (3)	0.0166 (3)	0.0010 (2)	0.0045 (2)	0.0005 (2)
C2	0.0133 (3)	0.0144 (3)	0.0158 (3)	0.0007 (2)	0.0045 (2)	0.0008 (2)
C3	0.0139 (3)	0.0132 (3)	0.0141 (3)	−0.0011 (2)	0.0036 (2)	0.0009 (2)
C4	0.0145 (3)	0.0128 (3)	0.0140 (3)	−0.0004 (2)	0.0025 (2)	−0.0003 (2)
C5	0.0122 (3)	0.0128 (3)	0.0138 (3)	0.0008 (2)	0.0036 (2)	−0.0014 (2)
C6	0.0119 (3)	0.0127 (3)	0.0127 (3)	−0.00011 (19)	0.00235 (19)	0.0000 (2)
C7	0.0131 (3)	0.0125 (3)	0.0160 (3)	0.0006 (2)	0.0043 (2)	0.0009 (2)
C8	0.0133 (3)	0.0130 (3)	0.0184 (3)	0.0002 (2)	0.0054 (2)	−0.0004 (2)
C9	0.0125 (3)	0.0149 (3)	0.0210 (3)	−0.0004 (2)	0.0037 (2)	0.0026 (2)
C10	0.0200 (3)	0.0173 (3)	0.0284 (4)	0.0029 (2)	0.0121 (3)	0.0069 (3)
C11	0.0199 (3)	0.0137 (3)	0.0218 (3)	0.0009 (2)	0.0071 (2)	0.0032 (2)
C12	0.0170 (3)	0.0142 (3)	0.0233 (3)	0.0029 (2)	0.0040 (2)	0.0029 (2)
C13	0.0191 (3)	0.0128 (3)	0.0256 (3)	0.0016 (2)	0.0115 (3)	0.0003 (2)

Geometric parameters (Å, º) top

O1—N3	1.2265 (8)	C7—C13	1.5044 (10)
O2—N3	1.2471 (8)	C7—C8	1.5080 (10)
O3—N4	1.2380 (9)	C8—C9	1.5330 (10)
O4—N4	1.2296 (8)	C8—H8A	0.9900
N1—C6	1.3551 (9)	C8—H8B	0.9900
N1—N2	1.3871 (8)	C9—C10	1.5328 (10)
N1—H1N1	0.887 (14)	C9—H9A	0.9900
N2—C7	1.2934 (9)	C9—H9B	0.9900
N3—C5	1.4517 (9)	C10—C11	1.5269 (11)
N4—C3	1.4525 (9)	C10—H10A	0.9900
C1—C2	1.3717 (10)	C10—H10B	0.9900
C1—C6	1.4241 (10)	C11—C12	1.5249 (11)
C1—H1A	0.9500	C11—H11A	0.9900
C2—C3	1.4026 (10)	C11—H11B	0.9900
C2—H2A	0.9500	C12—C13	1.5373 (11)
C3—C4	1.3772 (10)	C12—H12A	0.9900
C4—C5	1.3938 (10)	C12—H12B	0.9900
C4—H4A	0.9500	C13—H13A	0.9900
C5—C6	1.4237 (9)	C13—H13B	0.9900

C6—N1—N2	118.31 (6)	C7—C8—H8B	108.2
C6—N1—H1N1	117.1 (9)	C9—C8—H8B	108.2
N2—N1—H1N1	124.6 (9)	H8A—C8—H8B	107.4
C7—N2—N1	117.04 (6)	C10—C9—C8	115.71 (6)
O1—N3—O2	122.64 (6)	C10—C9—H9A	108.4
O1—N3—C5	118.93 (6)	C8—C9—H9A	108.4
O2—N3—C5	118.43 (6)	C10—C9—H9B	108.4
O4—N4—O3	123.61 (7)	C8—C9—H9B	108.4
O4—N4—C3	118.53 (6)	H9A—C9—H9B	107.4
O3—N4—C3	117.86 (6)	C11—C10—C9	115.46 (6)
C2—C1—C6	121.51 (6)	C11—C10—H10A	108.4
C2—C1—H1A	119.2	C9—C10—H10A	108.4
C6—C1—H1A	119.2	C11—C10—H10B	108.4
C1—C2—C3	119.69 (6)	C9—C10—H10B	108.4
C1—C2—H2A	120.2	H10A—C10—H10B	107.5
C3—C2—H2A	120.2	C12—C11—C10	114.80 (6)
C4—C3—C2	121.37 (6)	C12—C11—H11A	108.6
C4—C3—N4	118.83 (6)	C10—C11—H11A	108.6
C2—C3—N4	119.79 (6)	C12—C11—H11B	108.6
C3—C4—C5	118.95 (6)	C10—C11—H11B	108.6
C3—C4—H4A	120.5	H11A—C11—H11B	107.5
C5—C4—H4A	120.5	C11—C12—C13	113.89 (6)
C4—C5—C6	121.79 (6)	C11—C12—H12A	108.8
C4—C5—N3	115.84 (6)	C13—C12—H12A	108.8
C6—C5—N3	122.37 (6)	C11—C12—H12B	108.8
N1—C6—C5	123.46 (6)	C13—C12—H12B	108.8
N1—C6—C1	119.84 (6)	H12A—C12—H12B	107.7
C5—C6—C1	116.69 (6)	C7—C13—C12	115.46 (6)
N2—C7—C13	114.26 (6)	C7—C13—H13A	108.4
N2—C7—C8	124.44 (6)	C12—C13—H13A	108.4
C13—C7—C8	121.29 (6)	C7—C13—H13B	108.4
C7—C8—C9	116.32 (6)	C12—C13—H13B	108.4
C7—C8—H8A	108.2	H13A—C13—H13B	107.5
C9—C8—H8A	108.2

C6—N1—N2—C7	170.12 (6)	C4—C5—C6—N1	178.35 (6)
C6—C1—C2—C3	0.28 (10)	N3—C5—C6—N1	−0.87 (10)
C1—C2—C3—C4	−0.32 (10)	C4—C5—C6—C1	−0.89 (9)
C1—C2—C3—N4	179.83 (6)	N3—C5—C6—C1	179.89 (6)
O4—N4—C3—C4	−3.17 (10)	C2—C1—C6—N1	−178.97 (6)
O3—N4—C3—C4	176.68 (6)	C2—C1—C6—C5	0.30 (10)
O4—N4—C3—C2	176.69 (7)	N1—N2—C7—C13	−178.94 (6)
O3—N4—C3—C2	−3.46 (10)	N1—N2—C7—C8	−0.34 (10)
C2—C3—C4—C5	−0.26 (10)	N2—C7—C8—C9	−159.23 (7)
N4—C3—C4—C5	179.60 (6)	C13—C7—C8—C9	19.27 (10)
C3—C4—C5—C6	0.88 (10)	C7—C8—C9—C10	−74.34 (8)
C3—C4—C5—N3	−179.85 (6)	C8—C9—C10—C11	76.57 (9)
O1—N3—C5—C4	0.89 (9)	C9—C10—C11—C12	−59.37 (9)
O2—N3—C5—C4	−179.00 (6)	C10—C11—C12—C13	68.70 (9)
O1—N3—C5—C6	−179.84 (6)	N2—C7—C13—C12	−131.11 (7)
O2—N3—C5—C6	0.26 (10)	C8—C7—C13—C12	50.25 (9)
N2—N1—C6—C5	−177.98 (6)	C11—C12—C13—C7	−84.10 (8)
N2—N1—C6—C1	1.24 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2	0.888 (14)	1.947 (14)	2.6225 (9)	131.7 (12)
C2—H2A···O3ⁱ	0.95	2.52	3.3165 (10)	142

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₄O₄
M_r	292.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	6.9721 (1), 23.7359 (5), 8.2274 (2)
β (°)	102.351 (1)
V (Å³)	1330.03 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.51 × 0.45 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.946, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	26146, 5824, 4916
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.113, 1.04
No. of reflections	5824
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.30

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2	0.888 (14)	1.947 (14)	2.6225 (9)	131.7 (12)
C2—H2A···O3ⁱ	0.9500	2.5200	3.3165 (10)	142.00

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a postdoctoral research fellowship. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for Research University Golden Goose grant No. 1001/PFIZIK/811012.

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