4-[2-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-yl­idene)hydrazin-1-yl]benzo­nitrile

Çolak, N.; Yıldırır, Y.; Tercan, B.; Ermiş, E.; Hökelek, T.

doi:10.1107/S1600536810024025

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1784-o1785

doi:10.1107/S1600536810024025

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4-[2-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)hydrazin-1-yl]benzonitrile

Naki Çolak,^a Yılmaz Yıldırır,^b Barış Tercan,^c Emel Ermiş ^d and Tuncer Hökelek ^e ^*

^aDepartment of Chemistry, Hitit University, 19030 Ulukavak, Çorum, Turkey, ^bDepartment of Chemistry, Gazi University, 06500 Teknikokullar, Ankara, Turkey, ^cDepartment of Physics, Karabük University, 78050 Karabük, Turkey, ^dDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey, and ^eDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 17 June 2010; accepted 21 June 2010; online 26 June 2010)

In the title compound, C₁₃H₁₁N₃O₄, the dioxane ring adopts an envelope conformation with the C atom bonded to the dimethyl group in the flap position [deviation = 0.613 (1) Å]. The nitrile group and the attached benzene ring are roughly coplanar [maximum deviation = 0.087 (1) Å]. An intramolecular N—H⋯O hydrogen bond involving the hydrazinyl group generates an S(6) ring. The N—N and C—N bond lengths indicate that the compound may be a mixture of the azo and hydrazone tautomeric forms but the presence of the N-bound H atom supports the hydrazone form. The crystal structure is stabilized by weak intermolecular C—H⋯O, C—H⋯N and C—H⋯π interactions.

Related literature

For the applications of related azo compounds, see: Branger et al. (1997 ); Buchel et al. (1995 ); Gale et al. (1998 ); Ikeda & Tsutsumi (1995 ); Kang et al. (2000 ); Karcı et al. (2004 ); Kim et al. (1995 ); Kobrakov et al. (2004 ); Natansohn et al. (1992 ); Rochon et al. (1995 ). For related hydrazone structures, see: Çolak et al. (2010 ); Pavlovic et al. (2009 ); Seferoğlu et al. (2008 ); Seferoğlu et al. (2009 ); Wojciechowski & Szymezak (2007 ).

Experimental

Crystal data

C₁₃H₁₁N₃O₄
M_r = 273.25
Monoclinic, P 2₁ /n
a = 9.7617 (2) Å
b = 11.0023 (2) Å
c = 11.4753 (3) Å
β = 93.796 (1)°
V = 1229.76 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.46 × 0.43 × 0.29 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.950, T_max = 0.968
11746 measured reflections
3098 independent reflections
2591 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.108
S = 1.04
3098 reflections
225 parameters
All H-atom parameters refined
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.92 (2)	1.958 (16)	2.6674 (13)	132 (1)
C9—H9⋯N1ⁱ	0.94 (2)	2.624 (15)	3.5320 (16)	164 (1)
C10—H10⋯N3ⁱⁱ	0.99 (2)	2.485 (15)	3.3876 (16)	152 (1)
C12—H123⋯O2ⁱⁱⁱ	0.97 (2)	2.527 (17)	3.4454 (15)	159 (1)
C12—H122⋯Cg1^iv	0.98 (2)	2.491 (15)	3.4575 (13)	171 (1)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+2; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024025/ci5104sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024025/ci5104Isup2.hkl

checkCIF report

Comment top

It has been known for many years that the azo compounds are widely used class of dyes due to their applications in various fields such as the dyeing of textile fibers, the coloring of different materials, colored plastics and electrochemical sensors (Kobrakov et al., 2004; Karcı et al., 2004; Gale et al., 1998). Azo dyes have been attracting intensive interest for their potential use in optical data storage (Natansohn et al., 1992), optical switching (Ikeda & Tsutsumi, 1995), polarization holography (Kim et al., 1995; Rochon et al., 1995), optical modulation (Buchel et al., 1995), nonlinear optics (Branger et al., 1997) and photolabile surfactants (Kang et al., 2000).

The dyes may exist in two possible tautomeric forms, namely azo form and hydrazone form. The azo-hydrazone tautomerism is quite interesting from a theoretical and practical point of view because the two tautomers have different properties. Azo dyes are known to exist in the azo-hydrazone tautomeric forms (Çolak et al., 2010; Pavlovic et al., 2009; Seferoğlu et al., 2009; Seferoğlu et al., 2008; Wojciechowski & Szymezak, 2007). We herein report the crystal structure of the title compound, (I).

The title compound, (I), contains benzonitrile and 2,2-dimethyl-1,3-dioxane -4,6-dione groups connected via a hydrazinyl group (Fig. 1). In (I), N1—N2 [1.3082 (14) Å] bond length is between the N═N double bond [1.20–1.28 Å for a real azo compound] and N—N single bond [longer than 1.4 Å] lengths. The N1—C3 and N2—C5 bond lengths are 1.3116 (14) and 1.4075 (14) Å, respectively. The carbonyl O atoms O3 and O4 slightly deviate from the N1/C2–C4 plane by 0.255 (2) and 0.259 (2) Å, respectively. So, the title compound may exist both in azo and hydrazone tautomeric forms, and is mainly in the hydrazone tautomeric form. The C8—C13 [1.4418 (15) Å] bond length is longer for a C(sp²)—C(sp¹) bond, but in agreement with the previously reported value [1.442 (3) Å; Çolak et al., 2010).

An intramolecular N2—H2···O3 hydrogen bond (Table 1) results in the formation of a nearly planar [with a maximum deviation of 0.056 (1) Å for atom C4] six-membered ring C (O3/N1/N2/H2/C3/C4), which is oriented with respect to the benzonitrile ring B (C5–C10) at a dihedral angle of 7.8 (43)°. Atoms N1, N2, N3 and C13 are displaced by -0.162 (2), 0.038 (2), 0.049 (2) and 0.028 (2) Å from the plane of ring B, respectively. The benzonitrile and hydrazinyl groups (4-hydrazinylbenzonitrile) are essentially coplanar [with a maximum deviation of -0.087 (1) Å for atom N1]. The dioxane ring A (O1/O2/C1–C4) is not planar having envelope conformation with atom C1 displaced by 0.613 (1) Å from the plane of the other ring atoms.

In the crystal structure, weak C—H···O and C—H···N hydrogen bonds (Table 1) may be effective in the stabilization of the crystal packing. There also exists a weak C—H···π interaction (Table 1).

Related literature top

For the applications of related azo compounds, see: Branger et al. (1997); Buchel et al. (1995); Gale et al. (1998); Ikeda & Tsutsumi (1995); Kang et al. (2000); Karcı et al. (2004); Kim et al. (1995); Kobrakov et al. (2004); Natansohn et al. (1992); Rochon et al. (1995). For related hydrazone structures, see: Çolak et al. (2010); Pavlovic et al. (2009); Seferoğlu et al. (2008); Seferoğlu et al. (2009); Wojciechowski & Szymezak (2007).

Experimental top

A hydrochloric acid solution (2.5 ml) of 4-aminobenzonitrile (1.18 g, 10 mmol) and an aqueous solution (10 ml) of sodium nitrite (0.69 g, 10 mmol) were mixed and stirred at 273 K for 1 h. To this solution, an ethanol solution (10 ml) of the coupling component 2,2-dimethyl-1,3-dioxane-4,6-dione (1.44 g, 10 mmol) was added and the stirring was continued at 273 K for 4 h. The resulting product was filtered and washed with water, dried and crystallized from ethanol (yield 1.88 g, 69%; m.p. 440–442 K).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a hydrogen bond.

4-[2-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)hydrazin-1-yl]benzonitrile top

Crystal data top

C₁₃H₁₁N₃O₄	F(000) = 568
M_r = 273.25	D_x = 1.476 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4103 reflections
a = 9.7617 (2) Å	θ = 2.6–28.4°
b = 11.0023 (2) Å	µ = 0.11 mm⁻¹
c = 11.4753 (3) Å	T = 100 K
β = 93.796 (1)°	Block, yellow
V = 1229.76 (5) Å³	0.46 × 0.43 × 0.29 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3098 independent reflections
Radiation source: fine-focus sealed tube	2591 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.950, T_max = 0.968	k = −14→14
11746 measured reflections	l = −15→8

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0626P)² + 0.2729P] where P = (F_o² + 2F_c²)/3
3098 reflections	(Δ/σ)_max = 0.001
225 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₃H₁₁N₃O₄	V = 1229.76 (5) Å³
M_r = 273.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7617 (2) Å	µ = 0.11 mm⁻¹
b = 11.0023 (2) Å	T = 100 K
c = 11.4753 (3) Å	0.46 × 0.43 × 0.29 mm
β = 93.796 (1)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3098 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2591 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.968	R_int = 0.029
11746 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.108	All H-atom parameters refined
S = 1.04	Δρ_max = 0.38 e Å⁻³
3098 reflections	Δρ_min = −0.24 e Å⁻³
225 parameters

Special details top

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	0.16363 (8)	0.74524 (7)	0.85585 (7)	0.0172 (2)
O2	0.17892 (8)	0.56739 (7)	0.97179 (7)	0.01470 (19)
O3	0.35656 (9)	0.44276 (8)	0.96914 (7)	0.0187 (2)
O4	0.32521 (9)	0.79574 (8)	0.73794 (8)	0.0249 (2)
N1	0.44403 (10)	0.56888 (9)	0.76510 (9)	0.0165 (2)
N2	0.51381 (10)	0.46953 (9)	0.78943 (9)	0.0159 (2)
H2	0.4942 (16)	0.4243 (15)	0.8538 (15)	0.028 (4)*
N3	1.03756 (11)	0.29578 (10)	0.47015 (10)	0.0232 (2)
C1	0.08704 (11)	0.64589 (10)	0.90176 (10)	0.0143 (2)
C2	0.27845 (12)	0.71950 (11)	0.79881 (10)	0.0172 (2)
C3	0.34022 (12)	0.59901 (10)	0.82608 (10)	0.0155 (2)
C4	0.29477 (11)	0.52812 (10)	0.92521 (10)	0.0144 (2)
C5	0.62374 (11)	0.43844 (10)	0.72180 (10)	0.0148 (2)
C6	0.64458 (13)	0.49922 (11)	0.61746 (10)	0.0173 (2)
H6	0.5852 (15)	0.5636 (14)	0.5904 (13)	0.020 (4)*
C7	0.75216 (13)	0.46401 (11)	0.55177 (10)	0.0175 (2)
H7	0.7668 (15)	0.5059 (14)	0.4788 (13)	0.024 (4)*
C8	0.83788 (12)	0.36875 (11)	0.59035 (10)	0.0155 (2)
C9	0.81720 (12)	0.30898 (11)	0.69557 (10)	0.0161 (2)
H9	0.8752 (14)	0.2457 (14)	0.7224 (12)	0.020 (4)*
C10	0.70992 (12)	0.34407 (11)	0.76131 (10)	0.0159 (2)
H10	0.6926 (14)	0.3023 (14)	0.8350 (13)	0.021 (4)*
C11	0.01442 (13)	0.57371 (11)	0.80405 (10)	0.0178 (2)
H111	0.0795 (15)	0.5338 (14)	0.7556 (13)	0.022 (4)*
H112	−0.0444 (15)	0.5101 (14)	0.8393 (13)	0.023 (4)*
H113	−0.0456 (15)	0.6270 (15)	0.7544 (14)	0.026 (4)*
C12	−0.00717 (13)	0.70098 (11)	0.98606 (10)	0.0169 (2)
H121	0.0494 (16)	0.7364 (15)	1.0534 (13)	0.026 (4)*
H122	−0.0616 (15)	0.7636 (14)	0.9446 (13)	0.021 (4)*
H123	−0.0673 (16)	0.6388 (16)	1.0133 (15)	0.035 (4)*
C13	0.94875 (12)	0.32918 (11)	0.52248 (10)	0.0177 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0168 (4)	0.0111 (4)	0.0244 (4)	0.0003 (3)	0.0057 (3)	0.0024 (3)
O2	0.0132 (4)	0.0139 (4)	0.0169 (4)	0.0027 (3)	0.0012 (3)	0.0015 (3)
O3	0.0164 (4)	0.0178 (4)	0.0220 (4)	0.0033 (3)	0.0011 (3)	0.0027 (3)
O4	0.0244 (5)	0.0191 (5)	0.0321 (5)	0.0004 (4)	0.0096 (4)	0.0083 (4)
N1	0.0144 (5)	0.0146 (5)	0.0204 (5)	−0.0002 (4)	0.0009 (4)	−0.0023 (4)
N2	0.0151 (5)	0.0149 (5)	0.0179 (5)	0.0004 (4)	0.0031 (4)	−0.0005 (4)
N3	0.0227 (6)	0.0233 (6)	0.0244 (5)	0.0003 (4)	0.0076 (4)	0.0001 (4)
C1	0.0135 (5)	0.0111 (5)	0.0182 (5)	0.0005 (4)	0.0010 (4)	0.0024 (4)
C2	0.0152 (6)	0.0159 (6)	0.0208 (5)	−0.0001 (4)	0.0025 (4)	−0.0003 (4)
C3	0.0143 (5)	0.0140 (5)	0.0184 (5)	−0.0005 (4)	0.0017 (4)	−0.0006 (4)
C4	0.0127 (5)	0.0135 (5)	0.0170 (5)	−0.0010 (4)	0.0008 (4)	−0.0027 (4)
C5	0.0119 (5)	0.0143 (5)	0.0182 (5)	−0.0024 (4)	0.0014 (4)	−0.0037 (4)
C6	0.0178 (6)	0.0137 (5)	0.0205 (5)	−0.0001 (4)	0.0014 (4)	0.0001 (4)
C7	0.0196 (6)	0.0155 (5)	0.0178 (5)	−0.0026 (4)	0.0039 (4)	0.0004 (4)
C8	0.0134 (5)	0.0155 (5)	0.0179 (5)	−0.0031 (4)	0.0028 (4)	−0.0022 (4)
C9	0.0137 (5)	0.0160 (5)	0.0185 (5)	0.0003 (4)	0.0001 (4)	−0.0002 (4)
C10	0.0144 (5)	0.0177 (5)	0.0155 (5)	−0.0026 (4)	0.0010 (4)	−0.0004 (4)
C11	0.0174 (6)	0.0170 (6)	0.0188 (5)	0.0019 (5)	−0.0009 (4)	−0.0015 (4)
C12	0.0162 (6)	0.0141 (5)	0.0207 (5)	0.0032 (4)	0.0037 (4)	0.0007 (4)
C13	0.0178 (6)	0.0167 (6)	0.0188 (5)	−0.0029 (4)	0.0024 (4)	0.0006 (4)

Geometric parameters (Å, º) top

O1—C1	1.4435 (13)	C6—C7	1.3878 (16)
O1—C2	1.3645 (13)	C6—H6	0.954 (15)
O2—C1	1.4493 (13)	C7—C8	1.3949 (17)
O2—C4	1.3533 (13)	C7—H7	0.974 (15)
O3—C4	1.2081 (14)	C8—C9	1.4012 (16)
O4—C2	1.2009 (14)	C8—C13	1.4418 (15)
N1—N2	1.3082 (14)	C9—C10	1.3854 (15)
N1—C3	1.3116 (14)	C9—H9	0.936 (15)
N2—C5	1.4075 (14)	C10—H10	0.986 (15)
N2—H2	0.922 (17)	C11—C1	1.5117 (16)
N3—C13	1.1473 (15)	C11—H111	0.976 (15)
C1—C12	1.5055 (15)	C11—H113	0.984 (16)
C2—C3	1.4812 (16)	C11—H112	1.007 (16)
C3—C4	1.4718 (15)	C12—H122	0.975 (15)
C5—C6	1.3981 (16)	C12—H121	0.999 (16)
C5—C10	1.3932 (17)	C12—H123	0.967 (17)

C2—O1—C1	118.66 (9)	C7—C6—H6	119.7 (9)
C4—O2—C1	118.29 (8)	C6—C7—C8	119.80 (11)
N2—N1—C3	120.47 (10)	C6—C7—H7	119.6 (9)
N1—N2—C5	119.38 (10)	C8—C7—H7	120.6 (9)
N1—N2—H2	119.3 (10)	C7—C8—C9	120.56 (10)
C5—N2—H2	121.1 (10)	C7—C8—C13	120.76 (10)
O1—C1—O2	109.71 (9)	C9—C8—C13	118.68 (11)
O1—C1—C11	110.85 (9)	C8—C9—H9	120.9 (9)
O1—C1—C12	106.43 (9)	C10—C9—C8	119.72 (11)
O2—C1—C11	109.92 (9)	C10—C9—H9	119.4 (9)
O2—C1—C12	105.40 (9)	C5—C10—H10	119.5 (9)
C12—C1—C11	114.31 (10)	C9—C10—C5	119.50 (10)
O1—C2—C3	114.85 (10)	C9—C10—H10	121.0 (9)
O4—C2—O1	119.33 (11)	C1—C11—H111	111.6 (9)
O4—C2—C3	125.66 (11)	C1—C11—H113	110.4 (9)
N1—C3—C2	115.57 (10)	C1—C11—H112	108.6 (9)
N1—C3—C4	124.16 (11)	H111—C11—H112	109.0 (12)
C4—C3—C2	119.88 (10)	H111—C11—H113	108.9 (13)
O2—C4—C3	116.02 (10)	H113—C11—H112	108.3 (12)
O3—C4—O2	119.38 (10)	C1—C12—H121	108.9 (9)
O3—C4—C3	124.52 (10)	C1—C12—H122	107.9 (8)
C6—C5—N2	121.03 (11)	C1—C12—H123	109.4 (10)
C10—C5—N2	117.89 (10)	H121—C12—H123	110.0 (13)
C10—C5—C6	121.08 (10)	H122—C12—H121	110.9 (13)
C5—C6—H6	120.9 (9)	H122—C12—H123	109.6 (13)
C7—C6—C5	119.34 (11)	N3—C13—C8	178.56 (13)

C2—O1—C1—O2	51.23 (12)	O4—C2—C3—N1	−9.81 (19)
C2—O1—C1—C11	−70.35 (13)	O4—C2—C3—C4	163.35 (12)
C2—O1—C1—C12	164.79 (10)	N1—C3—C4—O2	−174.73 (10)
C1—O1—C2—O4	163.20 (11)	N1—C3—C4—O3	8.59 (19)
C1—O1—C2—C3	−21.07 (14)	C2—C3—C4—O2	12.73 (16)
C4—O2—C1—O1	−50.36 (12)	C2—C3—C4—O3	−163.95 (11)
C4—O2—C1—C12	−164.59 (9)	N2—C5—C6—C7	−178.47 (10)
C4—O2—C1—C11	71.77 (12)	C10—C5—C6—C7	0.62 (18)
C1—O2—C4—O3	−163.46 (10)	N2—C5—C10—C9	178.44 (10)
C1—O2—C4—C3	19.68 (14)	C6—C5—C10—C9	−0.67 (18)
C3—N1—N2—C5	179.24 (10)	C5—C6—C7—C8	0.05 (18)
N2—N1—C3—C2	173.80 (10)	C6—C7—C8—C9	−0.65 (18)
N2—N1—C3—C4	0.97 (18)	C6—C7—C8—C13	178.87 (11)
N1—N2—C5—C6	−11.37 (17)	C7—C8—C9—C10	0.60 (18)
N1—N2—C5—C10	169.52 (10)	C13—C8—C9—C10	−178.93 (11)
O1—C2—C3—N1	174.77 (10)	C8—C9—C10—C5	0.06 (17)
O1—C2—C3—C4	−12.07 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.92 (2)	1.958 (16)	2.6674 (13)	132 (1)
C9—H9···N1ⁱ	0.94 (2)	2.624 (15)	3.5320 (16)	164 (1)
C10—H10···N3ⁱⁱ	0.99 (2)	2.485 (15)	3.3876 (16)	152 (1)
C12—H123···O2ⁱⁱⁱ	0.97 (2)	2.527 (17)	3.4454 (15)	159 (1)
C12—H122···Cg1^iv	0.98 (2)	2.491 (15)	3.4575 (13)	171 (1)

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) −x, −y+1, −z+2; (iv) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₄
M_r	273.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.7617 (2), 11.0023 (2), 11.4753 (3)
β (°)	93.796 (1)
V (Å³)	1229.76 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.46 × 0.43 × 0.29

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.950, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	11746, 3098, 2591
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.108, 1.04
No. of reflections	3098
No. of parameters	225
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.92 (2)	1.958 (16)	2.6674 (13)	132 (1)
C9—H9···N1ⁱ	0.94 (2)	2.624 (15)	3.5320 (16)	164 (1)
C10—H10···N3ⁱⁱ	0.99 (2)	2.485 (15)	3.3876 (16)	152 (1)
C12—H123···O2ⁱⁱⁱ	0.97 (2)	2.527 (17)	3.4454 (15)	159 (1)
C12—H122···Cg1^iv	0.98 (2)	2.491 (15)	3.4575 (13)	171 (1)

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) −x, −y+1, −z+2; (iv) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of X-ray diffractometer.

References

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Volume 66| Part 7| July 2010| Pages o1784-o1785

doi:10.1107/S1600536810024025

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-[2-(2,2-Di­methyl-4,6-dioxo-1,3-dioxan-5-yl­­idene)hydrazin-1-yl]benzo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[2-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)hydrazin-1-yl]benzonitrile