1-(2-Meth­oxy­phen­yl)-2-{[2-(2-meth­oxy­phen­yl)hydrazinyl­idene](nitro)­meth­yl}diazene

Eschwege, K.G. von; Muller, F.; Hill, T.N.

doi:10.1107/S1600536812004175

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o609

doi:10.1107/S1600536812004175

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1-(2-Methoxyphenyl)-2-{[2-(2-methoxyphenyl)hydrazinylidene](nitro)methyl}diazene

Karel G. von Eschwege,^a ^* Fabian Muller ^a and Tania N. Hill ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: veschwkg@ufs.ac.za

(Received 19 January 2012; accepted 31 January 2012; online 4 February 2012)

In the title compound, C₁₅H₁₅N₅O₄, a nitroformazan derivative, the formazan unit is essentially planar with an r.m.s. deviation of 0.0204 (6) Å and adopts a closed syn,s-cis configuration with an intramolecular N—H⋯N hydrogen bond. The formazan plane makes dihedral angles of 4.32 (5) and 24.35 (5)° with the benzene rings. The dihedral angle between the formazan plane and the nitro group is 12.58 (8)°. In the crystal, C—H⋯O interactions connect the molecules into an inversion dimer.

Related literature

For synthetic background, see: Pelkis et al. (1957 ). For applications of formazans, see: Irving (1977 ). For related structures, see: Gilroy et al. (2008 ); Laing (1977 ); Mito et al. (1997 ); von Eschwege et al. (2011 , 2012 ); von Eschwege & Swarts (2010 ).

Experimental

Crystal data

C₁₅H₁₅N₅O₄
M_r = 329.32
Triclinic, $[P \overline 1]$
a = 7.2025 (5) Å
b = 10.9574 (8) Å
c = 11.2190 (9) Å
α = 117.188 (2)°
β = 91.416 (2)°
γ = 107.251 (2)°
V = 738.66 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.25 × 0.21 × 0.06 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.668, T_max = 0.746
10250 measured reflections
3431 independent reflections
2824 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.11
S = 1.04
3431 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N2	1.10 (3)	1.73 (3)	2.6117 (15)	134 (3)
C17—H17B⋯O1ⁱ	0.98	2.47	3.3325 (16)	146
C27—H27C⋯O2ⁱ	0.98	2.65	3.3907 (17)	133
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812004175/is5057sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004175/is5057Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004175/is5057Isup3.cml

checkCIF report

Comment top

During synthesis of the versatile trace metal analysis dithizone reagent, aniline is first diazotized and then treated with nitromethane to form the bright orange–red nitroformazan product (Pelkis et al., 1957). Ammonia and hydrogen sulfide gas is used to substitute the nitro group with sulfur towards the formation of dithizone, the chemistry of which is extensively described by Irving (1977). Single crystal X-ray structures of nitroformazan derivatives were determined by Gilroy et al. (2008) and Mito et al. (1997), and the dithizone structure by Laing (1977), while we performed extensive DFT (von Eschwege et al., 2011) and electrochemistry studies (von Eschwege & Swarts, 2010) on the free ligand. We recently embarked on a study during which we synthesized a series of electronically altered dithizones for the purpose of investigating its altered redox and structural properties. During this process orange 1,5-bis(2-methoxyphenyl)-3-nitroformazan (I, Fig. 1) crystals suitable for X-ray crystallography were grown from an acetone solution overlaid with n-hexane.

The formazan backbone (N4—N3—C1—N1—N2) was found to be highly delocalized, showing minimal bond-length alternation [N1—N2 1.290 (1), N3—N4 1.301 (1), N1—C1 1.356 (2), N3—C1 1.325 (2) Å] which are similar to the values found by Gilroy et al. (2008) for the `closed' nitroformazan derivatives. The backbone was found to be essentially planar with an r.m.s. deviation of 0.0204 Å, and with a maximum deviation 0.0297 (8) Å for atom C1. The N—H bond in the expected intramolecular N—H···N hydrogen bond is elongated due to bridging with a distance of 1.10 (3) Å. Two additional hydrogen bond interactions (C17—H17B···O1ⁱ and C27—H27C···O2ⁱ; Table 1) are observed between the O atoms of the nitro substituent on the formazan backbone with an adjacent molecule, resulting in the formation of 'dimeric' unit (Fig. 2) and a parallel sheet configuration when viewed along the b-axis (Fig. 3). The nitro group is twisted by 12.58 (8)° relative to the plane of the formazan backbone, while average twisting is observed for the phenyl substituents [4.32 (5)° and 24.35 (5)°].

Related literature top

For synthetic background, see: Pelkis et al. (1957). For applications of formazans, see: Irving (1977). For related structures, see: Gilroy et al. (2008); Laing (1977); Mito et al. (1997); von Eschwege et al. (2011, 2012); von Eschwege & Swarts (2010).

Experimental top

Solvents (AR) purchased from Merck and reagents from Sigma–Aldrich were used without further purification. The ortho-methoxy derivative of nitroformazan was prepared according to the procedure reported by Pelkis et al. (1957). M.p. 164 °C; λ_max (dicloromethane) 362, 462 nm. δH (600 MHz, CDCl₃) 14.92 (1H, s, NH), 4.03 (6H, s, OCH₃), 8.00–7.04 (8H, m, C₆H₄).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Intermolecular hydrogen bond interactions (dashed bonds) of the title compound. Non-relevant H atoms have been omitted for clarity. [Symmetry code: (i) 1 - x, 1 - y, 1 - z.]
	Fig. 3. A packing diagram of the title compound, illustrating the parallel sheet configuration as viewed along the b axis.

1-(2-Methoxyphenyl)-2-{[2-(2-methoxyphenyl)hydrazinylidene](nitro)methyl}diazene top

Crystal data top

C₁₅H₁₅N₅O₄	Z = 2
M_r = 329.32	F(000) = 344
Triclinic, P1	D_x = 1.481 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2025 (5) Å	Cell parameters from 5015 reflections
b = 10.9574 (8) Å	θ = 3.0–28.4°
c = 11.2190 (9) Å	µ = 0.11 mm⁻¹
α = 117.188 (2)°	T = 100 K
β = 91.416 (2)°	Cuboid, red
γ = 107.251 (2)°	0.25 × 0.21 × 0.06 mm
V = 738.66 (10) Å³

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	3431 independent reflections
Radiation source: sealed tube	2824 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 512 pixels mm^-1	θ_max = 28.0°, θ_min = 2.1°
ϕ and ω scans	h = −9→7
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −10→14
T_min = 0.668, T_max = 0.746	l = −14→14
10250 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0567P)² + 0.2301P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.11	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.32 e Å⁻³
3431 reflections	Δρ_min = −0.22 e Å⁻³
223 parameters

Crystal data top

C₁₅H₁₅N₅O₄	γ = 107.251 (2)°
M_r = 329.32	V = 738.66 (10) Å³
Triclinic, P1	Z = 2
a = 7.2025 (5) Å	Mo Kα radiation
b = 10.9574 (8) Å	µ = 0.11 mm⁻¹
c = 11.2190 (9) Å	T = 100 K
α = 117.188 (2)°	0.25 × 0.21 × 0.06 mm
β = 91.416 (2)°

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	3431 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2824 reflections with I > 2σ(I)
T_min = 0.668, T_max = 0.746	R_int = 0.027
10250 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.11	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.32 e Å⁻³
3431 reflections	Δρ_min = −0.22 e Å⁻³
223 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.

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

	x	y	z	U_iso*/U_eq
C1	0.24373 (18)	0.35944 (13)	0.57201 (13)	0.0165 (3)
C11	0.20805 (18)	0.09665 (13)	0.23162 (13)	0.0163 (3)
C12	0.26683 (17)	0.09557 (13)	0.11311 (13)	0.0163 (3)
C13	0.22134 (18)	−0.03694 (14)	−0.00672 (13)	0.0187 (3)
H13	0.2594	−0.0385	−0.0877	0.022*
C14	0.11980 (19)	−0.16760 (14)	−0.00785 (14)	0.0201 (3)
H14	0.0874	−0.2579	−0.0901	0.024*
C15	0.06606 (18)	−0.16640 (13)	0.11022 (14)	0.0193 (3)
H15	0.0005	−0.2559	0.1095	0.023*
C16	0.10804 (18)	−0.03447 (13)	0.22960 (13)	0.0175 (3)
H16	0.0685	−0.0336	0.3101	0.021*
C17	0.4352 (2)	0.23340 (14)	0.00981 (14)	0.0202 (3)
H17A	0.5108	0.1675	−0.0269	0.03*
H17B	0.5198	0.3334	0.0357	0.03*
H17C	0.321	0.2022	−0.0598	0.03*
C21	0.26964 (17)	0.64157 (13)	0.49771 (13)	0.0161 (3)
C22	0.27401 (18)	0.65519 (13)	0.37900 (13)	0.0166 (3)
C23	0.27496 (19)	0.78593 (14)	0.38634 (13)	0.0188 (3)
H23	0.2767	0.796	0.3066	0.023*
C24	0.27338 (19)	0.90125 (13)	0.50974 (14)	0.0203 (3)
H24	0.2731	0.9897	0.5139	0.024*
C25	0.2722 (2)	0.88841 (14)	0.62726 (14)	0.0215 (3)
H25	0.2732	0.9684	0.7116	0.026*
C26	0.26962 (19)	0.75873 (14)	0.62146 (13)	0.0192 (3)
H26	0.2678	0.7497	0.7017	0.023*
C27	0.2702 (2)	0.54524 (15)	0.14037 (13)	0.0226 (3)
H27A	0.1481	0.5611	0.1218	0.034*
H27B	0.2725	0.4537	0.0645	0.034*
H27C	0.3848	0.6268	0.1502	0.034*
N1	0.24998 (15)	0.49180 (11)	0.59013 (11)	0.0178 (2)
N2	0.26924 (15)	0.50650 (11)	0.48294 (11)	0.0164 (2)
N3	0.23306 (15)	0.23476 (11)	0.46437 (11)	0.0174 (2)
N4	0.24656 (15)	0.23359 (11)	0.34850 (11)	0.0168 (2)
N5	0.23346 (15)	0.34848 (11)	0.69742 (11)	0.0178 (2)
O1	0.20306 (15)	0.44731 (10)	0.79751 (10)	0.0243 (2)
O2	0.25603 (15)	0.24155 (10)	0.69729 (10)	0.0246 (2)
O11	0.36796 (14)	0.22919 (9)	0.12699 (9)	0.0208 (2)
O21	0.27761 (14)	0.53657 (9)	0.26384 (9)	0.0210 (2)
H4	0.272 (5)	0.341 (4)	0.356 (3)	0.127 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0164 (6)	0.0176 (6)	0.0159 (6)	0.0044 (5)	0.0028 (4)	0.0094 (5)
C11	0.0154 (5)	0.0162 (5)	0.0161 (6)	0.0064 (5)	0.0006 (4)	0.0064 (5)
C12	0.0155 (5)	0.0164 (5)	0.0186 (6)	0.0064 (5)	0.0023 (5)	0.0093 (5)
C13	0.0199 (6)	0.0209 (6)	0.0168 (6)	0.0089 (5)	0.0039 (5)	0.0094 (5)
C14	0.0209 (6)	0.0166 (6)	0.0201 (7)	0.0078 (5)	0.0012 (5)	0.0060 (5)
C15	0.0192 (6)	0.0164 (6)	0.0240 (7)	0.0061 (5)	0.0013 (5)	0.0112 (5)
C16	0.0174 (6)	0.0201 (6)	0.0185 (6)	0.0076 (5)	0.0031 (5)	0.0115 (5)
C17	0.0219 (6)	0.0218 (6)	0.0204 (7)	0.0074 (5)	0.0069 (5)	0.0129 (5)
C21	0.0147 (5)	0.0156 (5)	0.0190 (6)	0.0051 (5)	0.0032 (5)	0.0092 (5)
C22	0.0159 (5)	0.0154 (5)	0.0169 (6)	0.0050 (5)	0.0027 (4)	0.0069 (5)
C23	0.0215 (6)	0.0190 (6)	0.0180 (6)	0.0071 (5)	0.0034 (5)	0.0108 (5)
C24	0.0223 (6)	0.0153 (6)	0.0236 (7)	0.0074 (5)	0.0022 (5)	0.0092 (5)
C25	0.0261 (6)	0.0176 (6)	0.0183 (6)	0.0098 (5)	0.0044 (5)	0.0054 (5)
C26	0.0215 (6)	0.0208 (6)	0.0167 (6)	0.0084 (5)	0.0048 (5)	0.0094 (5)
C27	0.0320 (7)	0.0222 (6)	0.0158 (6)	0.0111 (6)	0.0045 (5)	0.0098 (5)
N1	0.0163 (5)	0.0195 (5)	0.0175 (5)	0.0041 (4)	0.0023 (4)	0.0102 (4)
N2	0.0175 (5)	0.0163 (5)	0.0172 (5)	0.0053 (4)	0.0034 (4)	0.0098 (4)
N3	0.0161 (5)	0.0211 (5)	0.0165 (5)	0.0061 (4)	0.0026 (4)	0.0106 (4)
N4	0.0178 (5)	0.0163 (5)	0.0164 (5)	0.0059 (4)	0.0026 (4)	0.0081 (4)
N5	0.0183 (5)	0.0171 (5)	0.0163 (5)	0.0027 (4)	0.0019 (4)	0.0088 (4)
O1	0.0331 (5)	0.0208 (5)	0.0164 (5)	0.0081 (4)	0.0070 (4)	0.0077 (4)
O2	0.0335 (5)	0.0227 (5)	0.0237 (5)	0.0103 (4)	0.0056 (4)	0.0158 (4)
O11	0.0258 (5)	0.0171 (4)	0.0179 (5)	0.0038 (4)	0.0050 (4)	0.0095 (4)
O21	0.0334 (5)	0.0171 (4)	0.0150 (5)	0.0115 (4)	0.0060 (4)	0.0081 (4)

Geometric parameters (Å, º) top

C1—N3	1.3252 (16)	C21—C22	1.4063 (18)
C1—N1	1.3559 (16)	C21—N2	1.4111 (15)
C1—N5	1.4675 (16)	C22—O21	1.3588 (15)
C11—C16	1.3926 (17)	C22—C23	1.3949 (17)
C11—C12	1.4013 (18)	C23—C24	1.3872 (18)
C11—N4	1.4089 (16)	C23—H23	0.95
C12—O11	1.3608 (14)	C24—C25	1.3884 (19)
C12—C13	1.3911 (17)	C24—H24	0.95
C13—C14	1.3952 (18)	C25—C26	1.3869 (18)
C13—H13	0.95	C25—H25	0.95
C14—C15	1.3847 (19)	C26—H26	0.95
C14—H14	0.95	C27—O21	1.4319 (16)
C15—C16	1.3880 (18)	C27—H27A	0.98
C15—H15	0.95	C27—H27B	0.98
C16—H16	0.95	C27—H27C	0.98
C17—O11	1.4278 (15)	N1—N2	1.2897 (15)
C17—H17A	0.98	N3—N4	1.3005 (15)
C17—H17B	0.98	N4—H4	1.10 (3)
C17—H17C	0.98	N5—O2	1.2292 (14)
C21—C26	1.3953 (18)	N5—O1	1.2342 (15)

N3—C1—N1	134.09 (12)	O21—C22—C21	116.00 (11)
N3—C1—N5	112.67 (11)	C23—C22—C21	119.20 (11)
N1—C1—N5	113.09 (11)	C24—C23—C22	120.17 (12)
C16—C11—C12	120.02 (11)	C24—C23—H23	119.9
C16—C11—N4	122.24 (12)	C22—C23—H23	119.9
C12—C11—N4	117.68 (11)	C23—C24—C25	120.55 (12)
O11—C12—C13	125.15 (12)	C23—C24—H24	119.7
O11—C12—C11	115.31 (11)	C25—C24—H24	119.7
C13—C12—C11	119.54 (11)	C26—C25—C24	119.98 (12)
C12—C13—C14	119.96 (12)	C26—C25—H25	120
C12—C13—H13	120	C24—C25—H25	120
C14—C13—H13	120	C25—C26—C21	119.99 (12)
C15—C14—C13	120.36 (12)	C25—C26—H26	120
C15—C14—H14	119.8	C21—C26—H26	120
C13—C14—H14	119.8	O21—C27—H27A	109.5
C14—C15—C16	120.00 (11)	O21—C27—H27B	109.5
C14—C15—H15	120	H27A—C27—H27B	109.5
C16—C15—H15	120	O21—C27—H27C	109.5
C15—C16—C11	120.10 (12)	H27A—C27—H27C	109.5
C15—C16—H16	120	H27B—C27—H27C	109.5
C11—C16—H16	120	N2—N1—C1	114.18 (11)
O11—C17—H17A	109.5	N1—N2—C21	115.34 (10)
O11—C17—H17B	109.5	N4—N3—C1	117.69 (11)
H17A—C17—H17B	109.5	N3—N4—C11	117.09 (10)
O11—C17—H17C	109.5	N3—N4—H4	113.3 (17)
H17A—C17—H17C	109.5	C11—N4—H4	129.2 (17)
H17B—C17—H17C	109.5	O2—N5—O1	123.48 (11)
C26—C21—C22	120.09 (11)	O2—N5—C1	118.27 (11)
C26—C21—N2	123.72 (12)	O1—N5—C1	118.25 (11)
C22—C21—N2	116.18 (11)	C12—O11—C17	117.37 (10)
O21—C22—C23	124.80 (12)	C22—O21—C27	116.76 (10)

C16—C11—C12—O11	−178.36 (11)	C22—C21—C26—C25	0.55 (19)
N4—C11—C12—O11	4.19 (17)	N2—C21—C26—C25	179.30 (12)
C16—C11—C12—C13	1.18 (19)	N3—C1—N1—N2	−8.2 (2)
N4—C11—C12—C13	−176.26 (11)	N5—C1—N1—N2	176.64 (10)
O11—C12—C13—C14	178.79 (12)	C1—N1—N2—C21	178.01 (10)
C11—C12—C13—C14	−0.71 (19)	C26—C21—N2—N1	6.28 (17)
C12—C13—C14—C15	−0.8 (2)	C22—C21—N2—N1	−174.93 (11)
C13—C14—C15—C16	1.89 (19)	N1—C1—N3—N4	6.7 (2)
C14—C15—C16—C11	−1.41 (19)	N5—C1—N3—N4	−178.05 (10)
C12—C11—C16—C15	−0.12 (19)	C1—N3—N4—C11	−171.54 (10)
N4—C11—C16—C15	177.20 (11)	C16—C11—N4—N3	17.56 (18)
C26—C21—C22—O21	178.75 (11)	C12—C11—N4—N3	−165.06 (11)
N2—C21—C22—O21	−0.09 (16)	N3—C1—N5—O2	14.10 (16)
C26—C21—C22—C23	−1.06 (18)	N1—C1—N5—O2	−169.63 (10)
N2—C21—C22—C23	−179.90 (11)	N3—C1—N5—O1	−166.06 (11)
O21—C22—C23—C24	−179.23 (12)	N1—C1—N5—O1	10.20 (16)
C21—C22—C23—C24	0.57 (19)	C13—C12—O11—C17	−0.99 (18)
C22—C23—C24—C25	0.4 (2)	C11—C12—O11—C17	178.52 (10)
C23—C24—C25—C26	−1.0 (2)	C23—C22—O21—C27	−3.81 (18)
C24—C25—C26—C21	0.5 (2)	C21—C22—O21—C27	176.39 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2	1.10 (3)	1.73 (3)	2.6117 (15)	134 (3)
N4—H4···N1	1.10 (3)	2.42 (3)	2.8812 (16)	103 (2)
C17—H17B···O1ⁱ	0.98	2.47	3.3325 (16)	146
C27—H27C···O2ⁱ	0.98	2.65	3.3907 (17)	133

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₅O₄
M_r	329.32
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.2025 (5), 10.9574 (8), 11.2190 (9)
α, β, γ (°)	117.188 (2), 91.416 (2), 107.251 (2)
V (Å³)	738.66 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.21 × 0.06

Data collection
Diffractometer	Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.668, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	10250, 3431, 2824
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.11, 1.04
No. of reflections	3431
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.22

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2	1.10 (3)	1.73 (3)	2.6117 (15)	134 (3)
N4—H4···N1	1.10 (3)	2.42 (3)	2.8812 (16)	103 (2)
C17—H17B···O1ⁱ	0.98	2.47	3.3325 (16)	146.1
C27—H27C···O2ⁱ	0.98	2.65	3.3907 (17)	132.8

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

Financial assistance from the University of the Free State is gratefully acknowledged. We also express our gratitude towards SASOL and the South African National Research Foundation (SA-NRF/THRIP) for financial support of this project. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Imapct GbR, Bonn, Germany. Google Scholar
Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Laing, M. (1977). J. Chem. Soc. Perkin Trans. 2, pp. 1248–1252. CSD CrossRef Google Scholar
Mito, M., Takeda, K., Mukai, K., Azuma, N., Gleiter, M. R., Krieger, C. & Neugebaue, F. A. (1997). J. Phys. Chem. B, 101, 9517–9524. CSD CrossRef CAS Web of Science Google Scholar
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Volume 68| Part 3| March 2012| Page o609

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

1-(2-Meth­­oxy­phen­yl)-2-{[2-(2-meth­­oxy­phen­yl)hydrazinyl­­idene](nitro)­meth­yl}diazene

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

1-(2-Methoxyphenyl)-2-{[2-(2-methoxyphenyl)hydrazinylidene](nitro)methyl}diazene