1-(2-Meth-oxy-phen-yl)-2-{[2-(2-meth-oxy-phen-yl)hydrazinyl-idene](nitro)-meth-yl}diazene.

In the title compound, C(15)H(15)N(5)O(4), a nitro-formazan 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 intra-molecular 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 inter-actions connect the mol-ecules 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 = 329.32

Triclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.11

S = 1.04

3431 reflections

223 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.22 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004175/is5057sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812004175/is5057Isup3.cml

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

C15H15N5O4	Z = 2
Mr = 329.32	F(000) = 344
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0567P)2 + 0.2301P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.11	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.32 e Å−3
3431 reflections	Δρmin = −0.22 e Å−3
223 parameters

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) .